WO2005123873A1 - Organic electroluminescent device material, organic electroluminescent device, display and illuminating device - Google Patents

Organic electroluminescent device material, organic electroluminescent device, display and illuminating device Download PDF

Info

Publication number
WO2005123873A1
WO2005123873A1 PCT/JP2005/010552 JP2005010552W WO2005123873A1 WO 2005123873 A1 WO2005123873 A1 WO 2005123873A1 JP 2005010552 W JP2005010552 W JP 2005010552W WO 2005123873 A1 WO2005123873 A1 WO 2005123873A1
Authority
WO
WIPO (PCT)
Prior art keywords
general formula
organic
organic electroluminescent
electroluminescent device
tautomer
Prior art date
Application number
PCT/JP2005/010552
Other languages
French (fr)
Japanese (ja)
Inventor
Tomohiro Oshiyama
Masato Nishizeki
Eisaku Katoh
Hiroshi Kita
Original Assignee
Konica Minolta Holdings, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Konica Minolta Holdings, Inc. filed Critical Konica Minolta Holdings, Inc.
Priority to JP2006514709A priority Critical patent/JP4894513B2/en
Publication of WO2005123873A1 publication Critical patent/WO2005123873A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/348—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising osmium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • Organic electroluminescent device organic electroluminescent device
  • the present invention relates to a material for an organic electroluminescent device, a device for an organic electroluminescent device, a display device, and a lighting device.
  • ELD electroluminescent display
  • ELD components include an inorganic electroluminescent device and an organic electroluminescent device (hereinafter referred to as an organic EL device).
  • Inorganic electroluminescent devices have been used as flat light sources, but high voltage AC is required to drive the light emitting devices.
  • An organic EL device has a structure in which a light-emitting layer containing a compound that emits light is sandwiched between a cathode and an anode. Electrons and holes are injected into the light-emitting layer and recombined to generate excitons.
  • a stilbene derivative, a distyrylarylene derivative or a tris styrylarylene derivative is doped with a small amount of a phosphor to achieve an improvement in light emission luminance and a long life of the device. .
  • an element having an organic light-emitting layer obtained by using an 8-hydroxyquinoline aluminum complex as a host conjugate and adding a small amount of a phosphor thereto for example, JP-A-63-264692
  • a device having an organic light emitting layer in which a quinoline aluminum complex is used as a host conjugate and doped with a quinacridone dye for example, JP-A-3-255190
  • the generation ratio of a luminescent excited species is 25% because the generation ratio between a singlet exciton and a triplet exciton is 1: 3, Since the light extraction efficiency is about 20%, the limit of the external extraction quantum efficiency (ext) is 5%.
  • the upper limit of the internal quantum efficiency is 100. / o, so the luminous efficiency power is four times higher in principle than in the case of singlet excitation, and it is possible to obtain almost the same performance as a cold-cathode tube. .
  • Onoleto metal iodide complexes in which the central metal is platinum instead of iridium, have also attracted attention.
  • this type of complex there are many known examples in which ligands are characterized (for example, see Patent Documents:! To 5 and Non-Patent Document 1).
  • the light emission luminance and the light emission efficiency of the light emitting element are greatly improved as compared with the conventional element because the emitted light is derived from phosphorescence.
  • the light emission lifetime is shorter than that of the conventional device.
  • phosphorescent high-efficiency light-emitting materials are difficult to shorten the emission wavelength and improve the light-emitting life of the device, and can achieve sufficient performance for practical use. .
  • an electron-withdrawing group such as a fluorine atom, a trifluoromethyl group or a cyano group has been introduced as a substituent into phenylpyridine, and picolinic acid or virazabole-based ligand has been used as a ligand.
  • a ligand for example, see Patent Documents 6 to 13 and Non-Patent Documents:! To 4
  • the emission wavelength of the light-emitting material is shortened. While blue can be achieved and a highly efficient device can be achieved, the emission lifetime of the device tends to be degraded, and improvement of the trade-off has been required.
  • Patent Document 1 JP-A-2002-332291
  • Patent Document 2 JP 2002-332292 A
  • Patent Document 3 JP-A-2002-338588
  • Patent Document 4 JP-A-2002-226495
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2002-234894
  • Patent Document 6 WO 02/15645 pamphlet
  • Patent Document 7 JP-A-2003-123982
  • Patent Document 8 Japanese Patent Application Laid-Open No. 2002-117978
  • Patent Document 9 JP 2003-146996 A
  • Patent Document 10
  • Patent Document 11 International Publication No. 05/007767 pamphlet
  • Patent Document 12 WO 04/101707 pamphlet
  • Patent Document 13 JP 2005-053912 A
  • Non-Patent Document 1 Inorganic Chemistry, Vol. 41, No. 12, pp. 3055-3066 (2002)
  • Non-Patent Document 2 Aplied Physics Letters, Vol. 79, page 2082 (2001)
  • Non-Patent Document 3 Aplied Physics Letters, Vol. 83, page 3818 (2003)
  • Non-Patent Document 4 New Journal of Chemistry, 26 Vol., P. 1171 (2002) Disclosure of the Invention
  • An object of the present invention is to provide an organic EL element, a lighting device, and a display device, in which the emission wavelength is controlled, which exhibits high luminous efficiency, and which has a long emission life.
  • One embodiment of the present invention for achieving the above object is a metal complex having the following general formula (1) or a tautomer of the general formula (1) as a partial structure. It is a feature of the organic electroluminescent device material.
  • Z11 represents an atom group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • R 1, R 2 and R 3 each represent a hydrogen atom or a substituent.
  • M is the periodic table of the elements
  • FIG. 1 is a schematic diagram showing an example of a display device including an organic EL element.
  • FIG. 2 is a schematic diagram of a display unit A.
  • FIG. 3 is an equivalent circuit diagram of a driving circuit constituting a pixel.
  • FIG. 4 is a schematic diagram of a display device using a passive matrix method.
  • FIG. 5 is a schematic diagram of a sealing structure of an organic EL element OLED1-1.
  • FIG. 6 is a schematic diagram of a lighting device including an organic EL element.
  • a metal complex having the following general formula (1) or a tautomer of the general formula (1) as a partial structure, a tautomer of the following general formula (2) or the general formula (2) A metal complex having the following general formula (3) or a tautomer of the general formula (3) as a partial structure; a metal complex having the following general formula (4) or a general formula (4) )
  • Z11 represents an atom group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • R 1, R 2 and R 3 each represent a hydrogen atom or a substituent.
  • M is the periodic table of the elements
  • Z21 represents an atom group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • R 1, R 2 and R 3 each represent a hydrogen atom or a substituent.
  • M is the periodic table of the elements
  • Z31 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • X, ⁇ and ⁇ each represent a carbon atom or a nitrogen atom which may have a substituent.
  • N (R) where at least two are nitrogen atoms or N (R) (where R is a hydrogen atom or
  • C represents a carbon atom.
  • M is group 8 in the periodic table
  • Z41 represents an atom group necessary for forming an aromatic heterocyclic ring. X and X are replaced
  • C 1, C 2 and C 3 each have a carbon atom
  • M represents a metal belonging to Groups 8 to 10 in the periodic table.
  • the bond between 41 42 41 42 41 43 42 43 represents a single bond or a double bond.
  • Z51 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • X represents an oxygen atom or a sulfur atom.
  • R and R are a hydrogen atom or
  • Z61 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • X ⁇ represents a carbon atom or a nitrogen atom, each of which may have a substituent.
  • ⁇ is group 8 to group 10 in the periodic table
  • Z11 represents an atomic group necessary for forming an aromatic heterocyclic ring.
  • the organic electroluminescent device material according to (2) which is characterized by the above-mentioned (2).
  • the organic electroluminescent device material according to the above (1) which is a metal complex having the above-mentioned general formula (3) or a tautomer of the general formula (3) as a partial structure. Fees.
  • the organic electroluminescent device according to the above (1) which is a metal complex having the above general formula (4) or a tautomer of the general formula (4) as a partial structure. Fees.
  • the organic electroluminescent device according to the above (1) which is a metal complex having the above general formula (5) or a tautomer of the general formula (5) as a partial structure. Fees.
  • M is S, iridium or platinum.
  • M is S, iridium or platinum.
  • M is S, iridium or platinum.
  • X represents a carbon atom which may have a substituent
  • X represents a nitrogen atom or —N (R) — (where R represents a hydrogen atom or a substituent).
  • M is iridium or platinum.
  • M is iridium or platinum.
  • M is S, iridium or platinum.
  • An organic electroluminescent device comprising the organic electroluminescent device according to any one of (1) to (21).
  • hole blocking layer as a constituent layer, wherein the hole blocking layer contains the organic electroluminescent device material according to any one of (1) to (21).
  • a light-emitting layer as a constituent layer wherein the light-emitting layer has a ring structure in which at least one of carbon atoms of a carboline derivative or a hydrocarbon ring constituting a carboline ring of the carboline derivative is substituted with a nitrogen atom.
  • the organic electroluminescent device according to any one of the above items (22) to (25), further comprising a derivative having a ring structure.
  • a display device comprising the organic electorescence luminescent element according to any one of (22) to (26).
  • a lighting device comprising the organic electorophore luminescent element according to any one of (22) to (26).
  • the composition defined in any one of the above (1) to (21) is used to molecularly design an organic EL device material useful for an organic EL device. It worked. Further, by using the organic EL element material, it was possible to provide an organic EL element, a lighting device, and a display device exhibiting high luminous efficiency and having a long luminous life.
  • phenylviridine (a 6-membered ring and a 6-membered
  • the mother nucleus of the compound represented by the general formulas (1) to (6) is represented by an aromatic hydrocarbon ring or an aromatic heterocyclic ring (preferably 6-membered). Ring) and an aromatic heterocyclic ring (preferably a 5-membered ring) are connected by a carbon-carbon bond or a carbon-nitrogen bond to form a metal complex having a specific partial structure.
  • the present invention provides a molecular design for imparting a function of controlling the emission wavelength of a metal complex to a long-wave region by introducing a substituent having a long-wavelength emission wavelength as a substituent.
  • the selection of an appropriate partial structure by using the basic skeleton of the general formulas (1) to (6) or each tautomer of the general formulas (1) to (6) as a starting point. Is possible.
  • a layer containing a metal complex having a partial structure of the general formulas (1) to (6) or each of the tautomers of the general formulas (1) to (6) according to the present invention a light emitting layer And / or a hole-blocking layer is preferred.
  • the compound when contained in the light-emitting layer, it can be used as a light-emitting dopant in the light-emitting layer to increase the efficiency of the external extraction quantum efficiency of the organic EL device of the present invention ( (Higher brightness) and a longer luminescent life.
  • the aromatic hydrocarbon ring represented by Z11 includes a benzene ring, a biphenyl ring, a naphthalene ring, an azulene ring, an anthracene ring, and a phenanthrene ring.
  • a benzene ring is preferably used.
  • the aromatic hydrocarbon ring has a substituent represented by R 1, R 2, R 3 in the general formula (1) described below.
  • the aromatic complex ring represented by Z11 includes a furan ring, a thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, Pyrazine ring, triazine ring, benzimidazole ring, oxaziazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, Examples include a phthalazine ring, a carbazole ring, a carboline ring, and a ring in which at least one of carbon atoms of a hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom.
  • a pyridine ring is preferable.
  • the aromatic heterocyclic ring may have a substituent represented by R 1, R 2 and R 3 in the above-mentioned general formula (1).
  • the ring represented by R11 is preferably an aromatic heterocyclic ring.
  • the aromatic ring (corresponding to Z11 in the present invention) linked thereto is In the case of an aromatic heterocycle, the stability of the molecule is improved, and the emission wavelength is shorter.
  • each is represented by R 1, R 2, and R 3.
  • substituents include, for example, an alkyl group (for example, a methyl group, an ethyl group, an isopropylinole group, a hydroxyethyl group, a methoxymethinole group, a trifluoromethyl group, a t_butyl group, etc.), a cycloalkyl group (for example, , A cyclopentyl group, a cyclohexyl group, etc.), an aralkyl group (eg, a benzyl group, a 2-phenyl group, etc.), an aromatic hydrocarbon group (eg, a phenyl group, a p-chlorophenyl group, a mesityl group, a tolyl group, a xylyl group) Group, biphenylyl group, naphthyl group, anthryl group, phenanthryl group, etc.), aromatic heterocyclic group (for example, furyl group, chen,
  • At least one of the groups represented by R 1, R 2 and R 3 is
  • It is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • Platinum (Pt) and iridium (Ir) are preferably used among the powers representing metals of group 8 to 10 (which may be metal atoms or ions).
  • M may be a metal.
  • a coordination bond is formed (also called complex formation) with a core metal (which may be a metal or an ion) to form a metal complex.
  • the aromatic hydrocarbon ring represented by Z21 is the same as the general formula (1) or the tautomer of the general formula (1).
  • the aromatic complex ring represented by Z21 is the same as the general formula (1) or the tautomer of the general formula (1). In the body, it has the same meaning as the aromatic heterocyclic ring represented by Z11.
  • R 1, R 2 and R 3 are each represented by
  • the metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1).
  • the aromatic hydrocarbon ring represented by Z31 is the same as the general formula (1) or the tautomer of the general formula (1).
  • the aromatic complex ring represented by Z31 is the same as the general formula (1) or the tautomer of the general formula (1). In the body, it has the same meaning as the aromatic heterocyclic ring represented by Z11.
  • each is represented by X 1, X 2 and X 3
  • the substituent represented by R in N (R) is a group represented by the general formula (1) or a tautomer of the general formula (1).
  • the metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1).
  • X may have a substituent.
  • X and X are nitrogen atoms or N (R) (where R is hydrogen atom or
  • the aromatic complex ring represented by Z41 is represented by the general formula (1) or the tautomer of the general formula (1): It has the same meaning as the aromatic heterocyclic ring represented by Z11.
  • R of N (R) _ is represented by the general formula (1) or a tautomer of the general formula (1). Has the same meaning as the substituents represented by R 1, R 2 and R 3.
  • the metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1).
  • the aromatic hydrocarbon ring represented by Z51 is the same as the general formula (1) or the tautomer of the general formula (1).
  • the aromatic complex ring represented by Z51 is the same as the general formula (1) or the tautomer of the general formula (1). In the body, it has the same meaning as the aromatic heterocyclic ring represented by Z11.
  • the substituents are each represented by R 1, R 2 and R 3 in the general formula (1) or a tautomer of the general formula (1).
  • the metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1).
  • X is a sulfur atom
  • the aromatic hydrocarbon ring represented by Z61 is the same as the general formula (1) or the tautomer of the general formula (1). Has the same meaning as the aromatic hydrocarbon ring represented by Z11.
  • an aromatic compound represented by Z61 The prime ring has the same meaning as that of the aromatic heterocyclic ring represented by Z11 in the general formula (1) or a tautomer of the general formula (1).
  • the metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1).
  • the metal complex according to the organic EL device material of the present invention is described in, for example, ⁇ rganic Le magazine, vol3 , No. 16, p2579 to 2581 (2001), Inorganic Chemistry, Vol . 30, Vol . 85 ⁇ : 1687 (1991),].
  • the organic EL device When an organic EL device is produced using the organic EL device material of the present invention, it is preferable to use the organic EL device as a light emitting layer or a hole blocking layer among constituent layers of the organic EL device (details will be described later). .
  • the light emitting layer it is preferably used as a light emitting dopant.
  • the mixing ratio of the light-emitting host to the light-emitting host, which is the main component in the light-emitting layer, is preferably adjusted to 0.1% by mass to less than 30% by mass.
  • the light emitting dopant may be a mixture of a plurality of types of compounds, and the mixing partner may have a different structure.
  • Other metal complexes or phosphorescent dopants or fluorescent dopants having other structures may be used. Good.
  • dopants phosphorescent dopants, fluorescent dopants, and the like
  • metal complex used as the luminescent dopant
  • the light-emitting dopant is roughly classified into two types, a fluorescent dopant that emits fluorescence and a phosphorescent dopant that emits phosphorescence.
  • fluorescent dopant include coumarin-based dyes, pyran-based dyes, cyanine-based dyes, croconium-based dyes, squarium-based dyes, oxobenzanthracene-based dyes, fluorescein-based dyes, and rhodamine-based dyes And pyrylium dyes, perylene dyes, styrven dyes, polythiophene dyes, and rare earth complex fluorescent materials.
  • a typical example of the latter is preferably a complex compound containing a metal belonging to Group 8, 9, or 10 of the periodic table of the elements, and more preferably an iridium compound or an iridium compound. Sumidium compounds are the most preferred, and iridium compounds are the most preferred.
  • the light-emitting host used in the present invention is not particularly limited in structure, but is typically a carbazole derivative, a triarylamine derivative, an aromatic borane derivative, a nitrogen-containing complex ring compound, or thiophene.
  • a carbazole derivative a triarylamine derivative, an aromatic borane derivative, a nitrogen-containing complex ring compound, or thiophene.
  • a carboline derivative a diazaforce rubazole derivative and the like are preferably used.
  • carboline derivative diazaforce rubazole derivative, and the like
  • the present invention is not limited thereto. These compounds may be used as hole blocking materials.
  • the luminescent host used in the present invention may be a low-molecular compound, a high-molecular compound having a repeating unit, or a low-molecular compound having a polymerizable group such as a vinyl group or an epoxy group (evaporation-polymerizable luminescent host). Les, Les ,.
  • a compound which has a hole-transporting ability and an electron-transporting ability, prevents a longer wavelength of light emission, and has a high Tg (glass transition temperature) is preferable.
  • the blocking layer for example, an electron blocking layer and a hole blocking layer
  • the organic EL device material of the present invention is preferably used for the hole blocking layer, the electron blocking layer, and the like, particularly preferably for the hole blocking layer.
  • the metal complex according to the present invention described in any one of Claims 1 to 17 is used as a hole.
  • the blocking layer may be contained as a layer component of the electron blocking layer or the like in a state of 100% by mass, or may be another organic compound (for example, a compound used for a constituent layer of the organic EL device of the present invention). Etc. may be mixed.
  • the thickness of the blocking layer according to the present invention is preferably from 3 nm to:! OO nm, and more preferably from 5 nm to 30 nm.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a material having a function of transporting electrons and having a very small ability to transport holes, and blocking holes while transporting electrons. By doing so, the recombination probability of electrons and holes can be improved.
  • the hole blocking layer examples include, for example, JP-A Nos. 11-204258 and 11-204359, and “Organic EL Devices and Their Forefront of Industrialization (N.T. Issue) ”on page 237 and the like can be used as the hole blocking layer according to the present invention. Further, the configuration of the electron transport layer described below can be used as a hole blocking layer according to the present invention, if necessary.
  • Electron blocking layer >>
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material having a function of transporting holes and having an extremely small ability to transport electrons. By blocking the electrons, the recombination probability of electrons and holes can be improved. Further, the configuration of the hole transport layer described later can be used as an electron blocking layer as needed.
  • the organic EL device material of the present invention for the adjacent layer adjacent to the light emitting layer, that is, for the hole blocking layer and the electron blocking layer, particularly It is preferably used for a blocking layer.
  • the hole transport layer includes a material having a function of transporting holes.
  • a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transporting material is not particularly limited, and is conventionally used in photoconductive materials as a charge injecting and transporting material for holes and used as a hole injecting layer and a hole transporting layer in EL devices. Any known medium force can be selected and used.
  • the hole transporting material has any of hole injection or transport and electron barrier properties, and may be an organic substance or an inorganic substance.
  • triazole derivatives oxazidazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives And hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, especially thiophene oligomers.
  • the hole transporting material the above-mentioned materials can be used. It is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
  • aromatic tertiary amine compound and styrylamine compound include N, N, N ', N, 1-tetraphenyl-1,4,4'-diaminophenyl; N, ⁇ '-diphenyl-1N, ⁇ 1,1-bis (3-methylphenyl)-[1,1,1-biphenyl] -1,4,4-diamine (TPD); 2,2-bis (4-di- ⁇ -tolylaminophenyl) ) Propane; 1,1-bis (4-di- ⁇ -tolylaminophenyl) cyclohexane; ⁇ , ⁇ , ⁇ ', ⁇ , tetra- ⁇ -tolyl-1,4,4'-diaminobiphenyl; 1,1- Bis (4-di- ⁇ -tolylaminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylme
  • a polymer material in which these materials are introduced into a polymer chain, or in which these materials are used as a polymer main chain, can also be used.
  • inorganic compounds such as p-type-Si and p-type-SiC can be used as hole injection materials and hole transport materials.
  • the hole transport material preferably has a high Tg.
  • the hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an inkjet method, and an LB method. That can be S.
  • the thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 500 nm.
  • the hole transport layer may have a single-layer structure composed of one or more of the above materials.
  • the electron transport layer is made of a material having a function of transporting electrons.
  • the electron transport layer includes an electron injection layer and a hole blocking layer.
  • the electron transport layer can have a single layer or a plurality of layers.
  • the electron transport material also serving as a hole blocking material
  • the electron transport layer adjacent to the light emitting layer on the cathode side is as follows. The following materials are known.
  • the electron transporting layer is not limited as long as it has a function of transmitting electrons injected from the cathode to the light emitting layer. Let's do it.
  • Examples of the material used for the electron transport layer include a nitro-substituted fluorene derivative, a diphenylquinone derivative, a thiopyran dioxide derivative, and a naphthalene derivative.
  • Examples include heterocyclic tetracarboxylic acid anhydrides such as phthalene perylene, phenolic imide, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, and oxaziazole derivatives.
  • a thiadiazole derivative in which an oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as the electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain, or in which these materials are used as a polymer main chain, can also be used.
  • a metal complex of an 8_quinolinol derivative for example, tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-18-quinolinol) aluminum, tris (5,7-dibutanol) 8_quinolinol) aluminum, tris (2-methyl_8_quinolinol) aluminum, tris (5-methyl_8_quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc.
  • Metal complexes that replace In, Mg, Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials.
  • methanol-free or metal phthalocyanine or those whose terminals are substituted with an alkyl group ⁇ sulfonic acid group or the like can be preferably used as the electron transporting material.
  • the distyryl virazine derivative exemplified as the material of the light emitting layer can be used as the electron transporting material, and like the hole injection layer and the hole transport layer, n-type—Si, n-type—SiC, etc.
  • Inorganic semiconductors can also be used as electron transport materials.
  • the electron transport layer is formed by thinning the electron transport material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an ink jet method, and an LB method. S can.
  • the thickness of the electron transport layer is not particularly limited, but is usually about 5 to 5000 nm.
  • the electron transport layer may have a single-layer structure made of one or more of the above materials.
  • the injection layer is provided as necessary, and has an electron injection layer and a hole injection layer. It may be present between the light emitting layer or the hole transporting layer and between the cathode and the light emitting layer or the electron transporting layer.
  • the injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the light emission luminance.
  • the organic EL element and the forefront of its industrialization June 30, 1998, N.T. For details, refer to Vol. 2, Chapter 2 “Electrode Materials” (pages 123 to 166) of “Ess Co., Ltd.”.
  • the anode buffer layer (hole injection layer) is also described in detail in JP-A-9-45479, JP-A-1260062, JP-A-8-288069, and the like.
  • cathode buffer electro injection layer
  • metal buffer represented by aluminum-aluminum
  • alkali metal compound buffer represented by lithium fluoride
  • alkaline earth metal compound buffer represented by magnesium fluoride
  • oxide represented by aluminum oxide
  • the buffer layer is an extremely thin film, and the thickness thereof is preferably in the range of 0.1 nm to 100 nm.
  • This injection layer can be formed by thin-filming the above-mentioned material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an ink jet method, and an LB method.
  • the thickness of the injection layer is not particularly limited, but is usually about 5 to 5000 nm.
  • the injection layer may have a single-layer structure made of one or more of the above materials.
  • a material having a large work function (4 eV or more), a metal, an alloy, an electrically conductive compound and a mixture thereof as an electrode material is preferably used.
  • electrode materials include metals such as Au, Cul, and indium tin oxide.
  • examples include conductive transparent materials such as Sido (ITO), SnO, and ⁇ . Also, IDIXO (In O-
  • a material which can produce an amorphous and transparent conductive film such as Zn ( II) may be used.
  • the anode is used to form a thin film by depositing these electrode materials by vapor deposition or sputtering, etc., and to form a pattern of a desired shape by one photolithography method. (about ⁇ m or more), and a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode substance.
  • the transmittance be greater than 10%
  • the sheet resistance of the anode is preferably several hundred ⁇ / port or less.
  • the film thickness is selected depending on the material, usually from 10 nm to: 1000 nm, preferably from 10 nm to 200 nm.
  • a metal having a low work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof are used as an electrode material.
  • electrode materials include sodium, sodium monolithium alloy, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al O) mixture, indium, lithium / aluminum mixture, rare
  • a mixture of an electron injecting metal and a second metal which is a metal having a large work function and a stable value such as a magnesium / silver mixture, Magnesium / aluminium mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3) mixture
  • the cathode can be manufactured by forming a thin film of these electrode materials by a method such as evaporation or sputtering.
  • the sheet resistance of the cathode is preferably several hundreds of ohms or less, and the preferred film thickness is usually selected in the range of 10 nm to 1000 nm, preferably 50 nm to 200 nm.
  • the anode S or the cathode S of the organic EL element is transparent or translucent or translucent, the light emission luminance is improved, which is advantageous.
  • Substrate also referred to as substrate, substrate, support, etc.
  • the substrate according to the organic EL device of the present invention is particularly suitable for glass, plastic, and the like.
  • the substrate is transparent, but preferably used substrates include, for example, glass, quartz, and a light-transmitting resin film.
  • a particularly preferred substrate is a resin film that can provide flexibility to the organic EL device.
  • Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyetherimide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC),
  • Examples of the film include cellulose triacetate (TAC) and cellulose acetate propionate (CAP).
  • the surface of the resin film, an inorganic material or coating or High Priestess Tsu Yogu water vapor permeability even de coating is formed 0. 01g / m 2 'day' atm following high barrier for both the organic Preferably it is a film.
  • the organic light-emitting device of the present invention has an external extraction efficiency at room temperature of preferably 1% or more, more preferably 2% or more.
  • quantum efficiency taken out (%) number of photons emitted to the outside of the organic EL element / number of electrons flowing to the organic EL element ⁇ 100.
  • a hue improvement filter such as a color filter may be used in combination.
  • a film having a roughened surface (such as an anti-glare finolem) may be used in combination to reduce uneven light emission.
  • a method for fabricating an organic EL device composed of a light-emitting layer, a hole blocking layer, an electron transport layer, a cathode buffer layer, and a cathode will be described.
  • a thin film made of a desired electrode material for example, a material for an anode is formed on an appropriate substrate by a method such as evaporation or sputtering so as to have a thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm.
  • a thin film containing an organic compound such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer, which are element materials, is formed thereon. Let it run.
  • Examples of the method of thinning the thin film containing the organic compound include a spin coating method, a casting method, an ink jet method, an evaporation method, and a printing method, as described above.
  • the vacuum deposition method or the spin coating method is particularly preferable because a pinhole is not easily generated. Further, a different film forming method may be applied to each layer. If you use the film adopts the deposition, the deposition conditions vary due to kinds of materials used, generally baud preparative heating temperature 50 ° C ⁇ 450 ° C, vacuum degree of 10- 6 Pa ⁇ 10- 2 It is desirable to appropriately select a pressure within a range of Pa, a deposition rate of 0.01 nm to 50 nm / sec, a substrate temperature of 50 ° C. to 300 ° C., and a film thickness of 0.1 nm to 5 zm.
  • a thin film made of a cathode material is formed thereon by a method such as evaporation or sputtering so as to have a thickness of 1 ⁇ m or less, preferably in the range of 50 nm to 200 nm.
  • a desired organic EL device can be obtained by forming and providing a cathode. In the production of this organic EL device, it is preferable to produce from the hole injection layer to the cathode consistently by one evacuation, but it is also possible to take it out in the middle and apply a different film forming method. At that time, consideration must be given to performing the work in a dry inert gas atmosphere.
  • the display device of the present invention will be described.
  • the display device of the present invention may be monochromatic or multicolored.
  • a multicolored display device will be described.
  • a shadow mask is provided only when the light-emitting layer is formed, and a film can be formed on one surface by an evaporation method, a casting method, a spin coating method, an inkjet method, a printing method, or the like.
  • the method is not particularly limited, but is preferably a vapor deposition method.
  • the production order can be reversed, and the cathode, the electron transport layer, the hole blocking layer, the light emitting layer, the hole transport layer, and the anode can be produced in this order.
  • the multicolor display device can be used as a display device, a display, and various light emission light sources.
  • full-color display can be achieved by using three types of organic EL elements that emit blue, red, and green light.
  • Examples of the display device and display include a television, a personal computer, a mopile device, an AV device, a character broadcast display, and information display in a car.
  • the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
  • Light-emitting light sources include home lighting, car interior lighting, backlights for watches and LCDs, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copiers, light sources for optical communication processors, and light sensors.
  • a light source or the like may be mentioned, but the light source is not limited thereto.
  • the lighting device of the present invention will be described.
  • the organic EL device of the present invention may be used as an organic EL device having a resonator structure, and the organic EL device having such a resonator structure may be used as a light source for an optical storage medium, an electronic device, or the like.
  • laser oscillation may be used for the above purpose.
  • the organic EL device of the present invention may be used as a kind of lamp such as an illumination light source or an exposure light source, a projection device of an image projection type, or a still image or a moving image. It can be used as a display device that can be viewed directly.
  • the drive method can be either a simple matrix (passive matrix) method or an active matrix method.
  • a full-color display device can be manufactured by using two or more kinds of the organic EL elements of the present invention having different emission colors.
  • FIG. 1 is a schematic diagram showing an example of a display device including an organic EL element.
  • FIG. 2 is a schematic view of a display such as a mobile phone for displaying image information by light emission of an organic EL element.
  • the display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
  • the control unit B is electrically connected to the display unit A, sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside, and controls the pixels for each scanning line by the scanning signal. , Sequentially emit light according to the image data signal, perform image scanning, and display image information on the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A.
  • the display section A has a wiring section including a plurality of scanning lines 5 and data lines 6 and a plurality of pixels 3 on a substrate.
  • the main members of the display unit A will be described below.
  • the figure shows a case where the light emitted from the pixel 3 is extracted in the white arrow direction (downward).
  • the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning line 5 and the data line 6 are orthogonal to each other in a grid pattern, and are connected to the pixels 3 at orthogonal positions ( Details are not shown).
  • the pixel 3 When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6, and emits light in accordance with the received image data.
  • the pixel 3 By properly arranging pixels in the red, green, and blue light emission regions on the same substrate, full color display is possible.
  • FIG. 3 is a schematic diagram of a pixel.
  • the pixel includes an organic EL device 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like. Red, green, and blue light emitting organic EL elements are used as the organic EL elements 10 for a plurality of pixels, and full-color display is performed by juxtaposing these on the same substrate. I can.
  • an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6. Then, when a scan signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5, the drive of the switching transistor 11 is turned on, and the image data signal applied to the drain is driven by the capacitor 13 It is transmitted to the gate of transistor 12.
  • the capacitor 13 is charged according to the potential of the image data signal, and the driving of the driving transistor 12 is turned on.
  • the drive transistor 12 has a drain connected to the power supply line 7, a source connected to the electrode of the organic EL element 10, and an organic EL element connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Element 10 is supplied with current.
  • the organic EL element 10 emits light by providing a switching transistor 11 and a driving transistor 12 as active elements for the organic EL elements 10 of each of the plurality of pixels, and The element 10 emits light.
  • a light emitting method is called an active matrix method.
  • the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-valued image data signal having a plurality of gradation potentials, or light emission of a predetermined light emission amount by a binary image data signal. It may be on or off.
  • the potential of the capacitor 13 may be maintained until the next scan signal is applied, or may be discharged immediately before the next scan signal is applied. ,.
  • the running signal is not limited to the above-described active matrix system.
  • a passive matrix light emission drive in which the organic EL element emits light in accordance with the data signal only when the light is emitted may be used.
  • FIG. 4 is a schematic diagram of a display device using a passive matrix method.
  • a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
  • the pixels 3 connected to the applied scan line 5 emit light according to the image data signal.
  • the manufacturing cost can be reduced.
  • the organic EL material according to the present invention can also be applied to an organic EL element that emits substantially white light as a lighting device.
  • a plurality of light emitting colors are emitted simultaneously by a plurality of light emitting materials, and white light is obtained by mixing colors.
  • white light is obtained by mixing colors.
  • a combination of a plurality of emission colors a combination of three emission maximum wavelengths of the three primary colors of blue, green and blue may be used, or a combination of complementary colors such as blue and yellow, and blue-green and orange may be used. It may be one containing two emission maximum wavelengths.
  • the combination of light-emitting materials for obtaining a plurality of emission colors includes a combination of a plurality of phosphorescent or fluorescent light-emitting materials (light-emitting dopants) and a fluorescent or phosphorescent light-emitting material.
  • a combination of a dye material that emits light with the light of the light emitting material as excitation light and a good displacement can be achieved
  • the white organic electorophore luminescent device according to the present invention employs a method of combining a plurality of luminescent dopants. preferable.
  • the layer structure of the organic electroluminescent device for obtaining a plurality of luminescent colors includes a method in which a plurality of luminescent dopants are present in a single luminescent layer, and a method in which a plurality of luminescent layers are provided. Examples include a method in which dopants having different emission wavelengths are present in the layer, and a method in which minute pixels that emit light with different wavelengths are formed in a matrix.
  • a patterning may be performed by a metal mask, an inkjet printing method, or the like at the time of film formation, if necessary.
  • the electrode When patterning is performed, only the electrode may be patterned, or the electrode and the light emitting layer may be patterned or checked, and the entire element layer may be patterned or checked.
  • the light emitting material used for the light emitting layer is not particularly limited.
  • the light emitting material is suitable for a wavelength range corresponding to CF (color filter) characteristics.
  • the platinum complex according to the present invention or any of known luminescent materials may be selected and combined to whiten.
  • the white light-emitting organic EL element of the present invention can be used as a kind of light source and lighting device such as home lighting, in-car lighting, and exposure light as a light source for the display device and display.
  • a lamp it is usefully used for a display device such as a backlight of a liquid crystal display device.
  • a backlight such as a clock, a signboard advertisement, a traffic light, a light source such as an optical storage medium, a light source of an electronic photocopier, a light source of an optical communication processor, a light source of an optical sensor, and a display device are required.
  • a wide range of applications such as general household electric appliances.
  • the transparent support substrate provided with the ITO transparent electrodes was ultrasonically cleaned with isopropyl alcohol. Then, drying with dry nitrogen gas was performed, and UV ozone cleaning was performed for 5 minutes.
  • This transparent support substrate is fixed to the substrate holder of a commercially available vacuum evaporation system, while _NPD, CBP, Ir_12, BCP, and Alq are placed in five tantalum resistance heating boats, respectively, and the vacuum evaporation system ( (First vacuum chamber).
  • lithium fluoride was placed in a tantalum resistance heating boat, and aluminum was placed in a tungsten resistance heating boat, and they were attached to a second vacuum chamber of a vacuum evaporation apparatus.
  • the heating boat containing CBP and the boat containing Ir12 are independently passed through, and the deposition rate of CBP as a light emitting host and Ir-12 as a light emitting dopant becomes 100: 7. This was adjusted to a thickness of 30 nm to provide a light emitting layer.
  • the heating boat containing the BCP was energized and heated, and the deposition rate was set to 0.1 lm / sec.
  • a hole blocking layer having a thickness of lOnm at 0.2 nm / sec was provided.
  • the sheet was heated by energization, and an electron transport layer having a thickness of 40 nm was provided at a deposition rate of 0.1 nm / sec to 0.2 nm / sec.
  • a cathode buffer steam Chakusokudo 0. OlnmZ sec ⁇ 0. 02nmZ seconds at a film thickness of 0. 5 nm by supplying an electric current to the boat lithium fluoride-containing One layer was provided, and then a boat containing aluminum was energized to apply a 150 nm-thick cathode at a deposition rate of 1 nm / sec to 2 nmZ seconds.
  • the organic EL element was transferred to a glove box (a glove box replaced with a high-purity nitrogen gas having a purity of 99.999% or more) in a nitrogen atmosphere without being brought into contact with the atmosphere.
  • the organic EL element OLED1-1 was fabricated with the sealing structure replaced by.
  • Barium oxide 105 a water-trapping agent, is made of a high-purity barium oxide powder manufactured by Aldrich Co., Ltd. using a fluororesin semi-permeable membrane with adhesive (Microtex S-NTF8031Q manufactured by Nitto Denko). What was pasted on the sealing can 104 was prepared and used in advance. The sealing can was bonded to the organic EL element by using an ultraviolet-curing adhesive 107 and irradiating an ultraviolet lamp to bond the two together to produce a sealing element.
  • 101 is a glass substrate provided with a transparent electrode
  • 102 is an organic EL layer including the above-described hole injection / transport layer, light emitting layer, hole blocking layer, electron transport layer
  • 103 is a cathode.
  • organic EL element OLED1-1 As shown in Table 1, the organic EL elements OLED1-2 to OLED1-2 to luminescent host, luminescent dopant and hole blocking material were changed in the same manner, respectively. : 1-24 were prepared.
  • the organic EL element OLED1-1 to 1-24 is lit at room temperature (about 23 ° C to 25 ° C) at a constant current of 2.5 mA / cm 2 , and the light emission luminance (U [cd / m 2 ] Thereby, the external extraction quantum efficiency (77) was calculated.
  • the measurement of the light emission luminance used CS1000 made by Minolta).
  • the external extraction quantum efficiency was expressed as a relative value when the organic EL element OLED1-1 was set to 100.
  • the light emission lifetime was expressed as a relative value when the organic EL element OLED1-1 was set to 100.
  • a carboline derivative or a carbon atom constituting the carboline ring of the carboline derivative When a derivative having a ring structure in which at least one of carbon atoms of a hydrogen ring is further substituted with a nitrogen atom is used in combination with the light emitting layer, a carboline derivative or a hydrocarbon ring constituting the carboline ring of the carbine derivative is used.
  • a derivative having a ring structure in which at least one of the carbon atoms is further substituted with a nitrogen atom for the hole blocking layer the effect described in the present invention was further improved.
  • the transparent support substrate provided with the ITO transparent electrodes was ultrasonically cleaned with isopropyl alcohol. Then, drying with dry nitrogen gas was performed, and UV ozone cleaning was performed for 5 minutes.
  • the transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while a-NPD, CBP, Ir-12, BCP, and Alq were placed in five tantalum resistance heating boats, respectively. It was attached to a vacuum evaporation system (first vacuum tank).
  • lithium fluoride was placed in a resistance heating boat made of tantalum and aluminum was placed in a resistance heating boat made of tungsten, and they were attached to a second vacuum tank of a vacuum evaporation apparatus.
  • the heating boat containing CBP and the boat containing Ir12 are independently passed through, and the deposition rate of CBP as a light emitting host and Ir-12 as a light emitting dopant becomes 100: 7. This was adjusted to a thickness of 30 nm to provide a light emitting layer.
  • the heating boat containing the BCP was energized and heated, and the evaporation rate was set to 0. InmZ seconds.
  • a hole blocking layer having a thickness of 10 nm and a thickness of 0.2 nmZ seconds was provided. Further, the heating boat containing Alq was energized and heated to provide an electron transport layer having a thickness of 30 nm at a deposition rate of 0.1 nm / sec to 0.2 nmZ second.
  • barium oxide 105 which is a water trapping agent, is obtained by coating a high-purity barium oxide powder manufactured by Anoredrich Co. with a fluororesin semi-permeable membrane with an adhesive (Microtex
  • S-NTF8031Q (manufactured by Nitto Denko), which was attached to a glass sealing can 104, was used in advance as a preparation.
  • the sealing can was bonded to the organic EL element by using an ultraviolet-curing adhesive 107 and irradiating an ultraviolet lamp to bond the two together to produce a sealing element.
  • 101 is a glass substrate provided with a transparent electrode
  • 102 is an organic EL layer composed of the hole injection / transport layer, light emitting layer, hole blocking layer, electron transport layer, etc.
  • 103 is a cathode.
  • the organic EL elements OLED2-2 to 2-2 were prepared in the same manner except that the light-emitting host, the light-emitting dopant and the hole-blocking material were respectively changed. — 19 was made.
  • the external extraction quantum efficiency was represented by a relative value when the organic EL element OLED2-1 was set to 100, and the light emission life was represented by a relative value when the organic EL element OLED2-1 was set to 100.
  • the transparent support substrate provided with this ITO transparent electrode was ultrasonically treated with iso-propyl alcohol. Wash, dry with dry nitrogen gas, and perform UV ozone cleaning for 5 minutes.
  • This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while m-MTDATXA, Hl, Ir-12, BCP, and Alq were each placed in five tantalum resistance heating boats. , And attached to a vacuum evaporation system (first vacuum tank).
  • lithium fluoride was placed in a resistance heating boat made of tantalum and aluminum was placed in a resistance heating boat made of tungsten, and they were attached to a second vacuum tank of a vacuum evaporation apparatus.
  • the heating boat containing HI and the boat containing Ir_12 are independently conducted, and the deposition rate of HI as the light emitting host and Ir-12 as the light emitting dopant becomes 100: 7. This was adjusted to a thickness of 30 nm, and a light emitting layer was provided.
  • the heating boat containing the BCP was energized and heated to provide a hole blocking layer having a thickness of 10 nm at a deposition rate of 0.2 to 0.2 nm / sec. Further, the heating boat containing Alq was heated by being energized to provide an electron transporting layer having a thickness of 20 nm at a deposition rate of 0.1 nm / sec to 0.2 nm / sec.
  • the organic EL element OLED3-1 was fabricated with the sealing structure replaced by.
  • Barium oxide 105 a water-trapping agent, is made of high-purity barium oxide powder manufactured by Aldrich Co., Ltd., and sealed with a fluororesin semi-permeable membrane with adhesive (Mikuguchi Tex S-NTF8031Q manufactured by Nitto Denko). What was pasted on the can 104 was prepared in advance and used. UV curable adhesive for bonding cans and organic EL devices 1 Using 07, the two were adhered by irradiating an ultraviolet lamp to form a sealing element.
  • 101 is a glass substrate provided with a transparent electrode
  • 102 is an organic EL layer composed of the hole injection / transport layer, light emitting layer, hole blocking layer, electron transport layer, etc.
  • 103 is a cathode.
  • the organic EL devices OLED3-2 to 3 _23 were produced in the same manner except that the luminescent dopant and the hole blocking material were changed.
  • An organic EL device was prepared in the same manner as in Example 3 except that the deposition rate of HI as a light-emitting host and Ir-12 as a light-emitting dopant was changed from 100: 7 to 100: 4 in forming the light-emitting layer in Example 3. OLED4-1 was created.
  • Organic EL element OLED4— Lights up! ⁇ 4_19 at room temperature (about 25 to 25 °, constant current of 2.5 mA / cm 2 , and emission luminance immediately after starting lighting (U [cd / m 2 ]
  • the external extraction quantum efficiency () was calculated by measuring, where the emission luminance was measured using CS — 1000 (manufactured by Minolta), and the external extraction quantum efficiency was measured using the organic EL element OLED 4 — It was expressed as a relative value when 1 was taken as 100.
  • Organic EL device 1 ⁇ : 04_1 to 4_19 are continuously lit at room temperature under a constant current condition of 2.5 mA / cm 2 , and the time required to reach half the initial luminance ( ⁇ /)
  • the light emission life was expressed as a relative value with the organic EL element OLED4-1 as 100.
  • the organic EL device manufactured using the metal complex according to the present invention can achieve higher luminous efficiency and longer luminescent life than the comparative organic EL device.
  • a carboline derivative or a derivative having a ring structure in which at least one carbon atom of a hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom in the light emitting layer.
  • the use of a derivative or a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom for the hole blocking layer further enhances the present invention. The described effect was improved.
  • the transparent support substrate provided with the ITO transparent electrodes was ultrasonically cleaned with iso-propyl alcohol. Then, dry with dry nitrogen gas and perform UV ozone cleaning for 5 minutes.
  • the transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while five tantalum resistance heating boats were charged with m-MTDATXA, Hl, Ir-12, BCP, and Alq.
  • lithium fluoride was placed in a resistance heating boat made of tantalum, and aluminum was placed in a resistance heating boat made of tungsten, and they were attached to a second vacuum tank of a vacuum evaporation apparatus.
  • the heating boat containing HI and the boat containing Ir_12 were independently passed, and the deposition rate of HI as the light emitting host and Ir-12 as the light emitting dopant became 100: 7. This was adjusted to a thickness of 30 nm, and a light emitting layer was provided.
  • the heating boat containing the BCP was energized and heated, and the evaporation rate was set to 0. InmZ seconds.
  • a hole blocking layer having a thickness of 10 nm was provided at a thickness of 0.2 nm / sec. Further, the heating containing Alq
  • the boat was energized and heated to provide an electron transport layer with a thickness of 30 nm at a deposition rate of 0.1 nm / sec to 0.2 nm / sec.
  • barium oxide 105 a water-trapping agent
  • barium oxide 105 a water-trapping agent
  • a high-purity barium oxide powder manufactured by Aldrich Co., Ltd. with a fluororesin semi-permeable membrane (Microtex S-NTF8031Q manufactured by Nitto Denki) with an adhesive.
  • What was pasted on the sealing can 104 was prepared and used in advance.
  • the UV-curable adhesive 107 was used for bonding the EL device, and both were adhered by irradiating an ultraviolet lamp to produce a sealing element.
  • reference numeral 101 denotes a glass substrate provided with a transparent electrode
  • 102 denotes an organic EL layer including the above-described hole injection / transport layer, light emitting layer, hole blocking layer, electron transport layer
  • 103 denotes a cathode.
  • organic EL devices OLED5-2 to 5_25 were produced.
  • Organic EL element OLED5 Continuous lighting of! To 5-25 at room temperature under a constant current of 2.5 mA / cm2, and the time required to reach 90% of the initial luminance ( ⁇ / )
  • the external extraction quantum efficiency was expressed as a relative value when the organic EL element OLED5-1 was set to 100, and the emission life was expressed as a relative value when the organic EL element OLED5-1 was set to 100.
  • the organic EL device manufactured using the metal complex according to the present invention can achieve higher luminous efficiency and longer luminescent life than the comparative organic EL device.
  • a carboline derivative or a derivative having a ring structure in which at least one carbon atom of a hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom in the light emitting layer.
  • the use of a derivative or a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom for the hole blocking layer further enhances the present invention. The described effect was improved.
  • the organic EL element OLED6_2_6 was prepared in the same manner except that the light emitting host, the light emitting dopant, and the hole blocking material were respectively changed. 20 were produced. Evaluation was performed in the same manner as in Example 1 for the obtained organic EL element OLED6 — 16 — 20 and for the external extraction quantum efficiency.
  • the organic EL element OLED6 :: 6-20 is continuously lit at 25 ° C at a constant current of 2.5 mA / cm 2 , and the initial drive voltage of the drive voltage when the brightness reaches half of the initial brightness The rise from pressure was measured.
  • the organic EL device manufactured using the metal complex according to the present invention can achieve higher luminous efficiency and lower voltage rise than the comparative organic EL device.
  • a derivative having a ring structure in which at least one of carbon atoms of a carboline derivative or a hydrocarbon ring constituting a carboline ring of the carboline derivative is further substituted with a nitrogen atom.
  • the use of the compound in the light-emitting layer allows the carboline derivative or a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom to be a hole.
  • Use of the blocking layer further improved the effects described in the present invention.
  • the organic EL element OLED1-7 of Example 1 was used as a blue light emitting element.
  • Ir_l was used as a green light emitting device.
  • Ir_9 was used as a red light emitting element.
  • a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (pixels in a red region, pixels in a green region, pixels in a blue region, etc.)
  • the scanning lines 5 and the plurality of data lines 6 of the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid and are connected to the pixels 3 at orthogonal positions. (Details not shown).
  • the plurality of pixels 3 are driven by an active matrix method including an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal from a scanning line 5. When applied, it receives an image data signal from the data line 6 and emits light according to the received image data.
  • a full-color display device was manufactured by juxtaposing the red, green, and blue pixels as appropriate.
  • a full-color display device was produced in the same manner as in the production of the blue light-emitting device of Example 7, except that the organic EL elements OLED1-7 were changed to the organic EL elements OLED2-7.
  • the organic EL device OLED1-7 was replaced with the organic EL device OLED3-4.
  • a full-color display device was produced in the same manner except that the above was changed.
  • a full-color display device was fabricated in the same manner as in the fabrication of the blue light-emitting device of Example 7, except that the organic EL devices OLED1-7 were changed to the organic EL devices OLED4-4.
  • a full-color display device was produced in the same manner as in the production of the blue light-emitting device of Example 7, except that the organic EL elements OLED1-7 were changed to the organic EL elements OLED5-4.
  • a full-color display device was produced in the same manner as in the production of the blue light-emitting device of Example 7, except that the organic EL elements OLED1-7 were changed to the organic EL elements OLED6-5.
  • the device By driving the full-color display device, the device has high durability with high luminance, and It was found that a clear full-color moving image display could be obtained.
  • the electrode of the transparent electrode substrate of Example 1 was patterned into 20 mm X 20 mm, and a single NPD was formed thereon as a hole injection / transport layer with a thickness of 25 nm as in Example 1;
  • the above-mentioned heated boat containing CBP, the boat containing Compound 1-5 of the present invention, and the boat containing Ir_9 are supplied with current independently, and CBP as a light-emitting host and Compounds 1_5 and Ir_5 as light-emitting dopants of the present invention.
  • the deposition rate of 9 was adjusted so as to be 100: 5: 0.6, and the deposition was performed so as to have a thickness of 30 nm, thereby providing a light emitting layer.
  • a hole blocking layer was provided by forming a film of BCP to a thickness of 10 nm. Further, a film of Alq was formed at a thickness of 40 nm to provide an electron transport layer.
  • Example 2 a square perforated mask having substantially the same shape as the transparent electrode made of stainless steel was placed on the electron injection layer, and lithium fluoride 0.5 nm and the cathode were used as a cathode buffer layer.
  • lithium fluoride 0.5 nm and the cathode were used as a cathode buffer layer.
  • Fig. 6 shows a schematic diagram of a flat lamp.
  • Fig. 6 (a) shows a schematic plan view and Fig. 6 (b) shows a schematic cross-sectional view.
  • a white lighting device was manufactured in the same manner as in Example 13, except that the compound of the present invention 1-5 was changed to 2-7 in the manufacture of the white light-emitting device of Example 13.
  • Example 13 In preparation of the white light emitting device of Example 13, the present compound 115 was changed to 3-2. A white lighting device was produced in the same manner as in Example 13 except for the above.
  • a white lighting device was manufactured in the same manner as in Example 13, except that Compounds 1-5 were changed to 4-4 in the preparation of the white light-emitting device of Example 13.
  • a white light emitting device was produced in the same manner as in Example 13, except that Compound 1_5 was changed to 5-1 in preparation of the white light-emitting element of Example 13.
  • a white light device was produced in the same manner as in Example 13 except that Compound 15 was changed to 6-5 in preparation of the white light-emitting device of Example 13.
  • Organic EL devices OLED7— :! to 7-13 were prepared in the same manner as in Example 1, except that the light emitting dopant was changed to Ir_l and the hole blocking material was changed as shown in Table 7.
  • the light colors were all green.
  • an organic EL device material useful for an organic EL device is obtained.
  • the emission wavelength is controlled, high luminous efficiency is exhibited, and the luminescent lifetime is improved.
  • a long organic EL element, a lighting device, and a display device can be provided.

Abstract

Disclosed is an organic electroluminescent device material which is characterized by being composed of a metal complex having a substance represented by the general formula (1) below or a tautomer thereof as a partial structure. (1) [In the formula, Z11 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring; R11, R12 and R13 respectively represent a hydrogen atom or a substituent; and M11 represents a group 8-10 metal of the periodic table.]

Description

明 細 書  Specification
有機エレクト口ルミネッセンス素子材料、有機エレクト口ルミネッセンス素子 Organic electroluminescent device, organic electroluminescent device
、表示装置及び照明装置 , Display device and lighting device
技術分野  Technical field
[0001] 本発明は、有機エレクト口ルミネッセンス素子材料、有機エレクト口ルミネッセンス素 子、表示装置及び照明装置に関する。  The present invention relates to a material for an organic electroluminescent device, a device for an organic electroluminescent device, a display device, and a lighting device.
背景技術  Background art
[0002] 従来、発光型の電子ディスプレイデバイスとして、エレクト口ルミネッセンスディスプレ ィ（以下、 ELDという）がある。 ELDの構成要素としては、無機エレクト口ルミネッセン ス素子や有機エレクト口ルミネッセンス素子（以下、有機 EL素子とレ、う）が挙げられる 。無機エレクト口ルミネッセンス素子は平面型光源として使用されてきたが、発光素子 を駆動させるためには交流の高電圧が必要である。有機 EL素子は、発光する化合 物を含有する発光層を陰極と陽極で挟んだ構成を有し、発光層に電子及び正孔を 注入して、再結合させることにより励起子（エキシトン）を生成させ、このエキシトンが 失活する際の光の放出（蛍光'燐光）を利用して発光する素子であり、数 V〜数十 V 程度の電圧で発光が可能であり、さらに、 自己発光型であるために視野角に富み、 視認性が高ぐ薄膜型の完全固体素子であるために省スペース、携帯性等の観点か ら注目されている。  [0002] Conventionally, there is an electroluminescent display (hereinafter, referred to as ELD) as a light-emitting electronic display device. ELD components include an inorganic electroluminescent device and an organic electroluminescent device (hereinafter referred to as an organic EL device). Inorganic electroluminescent devices have been used as flat light sources, but high voltage AC is required to drive the light emitting devices. An organic EL device has a structure in which a light-emitting layer containing a compound that emits light is sandwiched between a cathode and an anode. Electrons and holes are injected into the light-emitting layer and recombined to generate excitons. This is an element that emits light by using light emission (fluorescence) when this exciton is deactivated. It can emit light at a voltage of several volts to several tens of volts. Because of this, it is a thin-film type solid-state device that has a wide viewing angle and high visibility, and is attracting attention from the viewpoint of space saving and portability.
[0003] し力 ながら、今後の実用化に向けた有機 EL素子においては、さらに低消費電力 で効率よく高輝度に発光する有機 EL素子の開発が望まれている。  [0003] However, in organic EL devices for practical use in the future, there is a demand for the development of an organic EL device that emits light with high efficiency and low power consumption.
[0004] 特許第 3093796号明細書では、スチルベン誘導体、ジスチリルァリーレン誘導体 またはトリススチリルァリーレン誘導体に、微量の蛍光体をドープし、発光輝度の向上 、素子の長寿命化を達成している。  [0004] In the specification of Japanese Patent No. 3093796, a stilbene derivative, a distyrylarylene derivative or a tris styrylarylene derivative is doped with a small amount of a phosphor to achieve an improvement in light emission luminance and a long life of the device. .
[0005] また、 8—ヒドロキシキノリンアルミニウム錯体をホストイ匕合物として、これに微量の蛍 光体をドープした有機発光層を有する素子（例えば、特開昭 63— 264692号公報） 、 8—ヒドロキシキノリンアルミニウム錯体をホストイ匕合物として、これにキナクリドン系 色素をドープした有機発光層を有する素子（例えば、特開平 3— 255190号公報）等 が知られている。 [0005] Further, an element having an organic light-emitting layer obtained by using an 8-hydroxyquinoline aluminum complex as a host conjugate and adding a small amount of a phosphor thereto (for example, JP-A-63-264692); A device having an organic light emitting layer in which a quinoline aluminum complex is used as a host conjugate and doped with a quinacridone dye (for example, JP-A-3-255190) It has been known.
[0006] 以上のように、励起一重項からの発光を用いる場合、一重項励起子と三重項励起 子の生成比が 1： 3であるため発光性励起種の生成確率が 25%であり、光の取り出し 効率が約 20%であるため、外部取り出し量子効率（ ext)の限界は 5%とされている  [0006] As described above, when light emission from an excited singlet is used, the generation ratio of a luminescent excited species is 25% because the generation ratio between a singlet exciton and a triplet exciton is 1: 3, Since the light extraction efficiency is about 20%, the limit of the external extraction quantum efficiency (ext) is 5%.
[0007] ところ力 プリンストン大より励起三重項からの燐光発光を用いる有機 EL素子の報 告（M. A. Baldo et al.， nature, 395卷、 151 _ 154ページ（1998年））力 Sされ て以来、室温で燐光を示す材料の研究が活発になってきている。 [0007] However, a report on organic EL devices using phosphorescence from triplets excited by Princeton University (MA Baldo et al., Nature, vol. 395, pp. 151-154 (1998)) Research on materials that show phosphorescence at room temperature has become active.
[0008] 例えば M. A. Baldo et al.， nature, 403卷、 17号、 750— 753ページ（2000 年）、また米国特許第 6， 097, 147号明細書等にも開示されている。  [0008] For example, it is disclosed in M. A. Baldo et al., Nature, Vol. 403, No. 17, pp. 750-753 (2000), and in US Pat. No. 6,097,147.
[0009] 励起三重項を使用すると、内部量子効率の上限が 100。/oとなるため、励起一重項 の場合に比べて原理的に発光効率力 S4倍となり、冷陰極管とほぼ同等の性能が得ら れる可能性があることから照明用途としても注目されている。  [0009] When the excited triplet is used, the upper limit of the internal quantum efficiency is 100. / o, so the luminous efficiency power is four times higher in principle than in the case of singlet excitation, and it is possible to obtain almost the same performance as a cold-cathode tube. .
[0010] 例えば、 S. Lamansky et al. , J. Am. Chem. Soc. , 123卷， 4304ページ（2 001年)等においては、多くの化合物がイリジウム錯体系等重金属錯体を中心に合 成検討されている。  [0010] For example, in S. Lamansky et al., J. Am. Chem. Soc., Vol. 123, p. 4304 (2001), many compounds are synthesized mainly from heavy metal complexes such as iridium complexes. Is being considered.
[0011] また、前述の M. A. Baldo et al. , nature, 403卷， 17号， 750— 753ページ（ 2000年）においては、ドーパントとして、トリス（2—フエ二ルビリジン）イリジウムを用い た検討がされている。  [0011] Also, in the aforementioned MA Baldo et al., Nature, Vol. 403, No. 17, pp. 750-753 (2000), a study was conducted using tris (2-phenylvinylidine) iridium as a dopant. ing.
[0012] その他、 M. E. Tompson等は、 The 10th International Workshop on In organic and Organic Electroluminescence (EL' 00、浜松) (こおレヽて、ドーノ ン卜として L Ir (acac)、例えば、 (ppy) Ir (acac)を、また、 Moon-Jae  [0012] In addition, ME Tompson et al., The 10th International Workshop on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu) (Korea, L Ir (acac) such as (ppy) Ir ( acac) and Moon-Jae
Youn. 0g、 Tetsuo Tsutsui等は、やはり、 The 10th International Works hop on Inorganic and Organic Electroluminescence (EL' 00、浜松)にお いて、ドーパントとして、トリス（2— (p—トリル）ピリジン)イリジウム（Ir (ptpy) )， トリス（ ベンゾ [h]キノリン)イリジウム（Ir (bzq) )等を用いた検討を行っている（なおこれらの 金属錯体は一般にオルトメタル化イリジウム錯体と呼ばれている。 )。  Youn. 0g, Tetsuo Tsutsui, et al. Also used Tris (2- (p-tolyl) pyridine) iridium (Ir (Ir) as a dopant in The 10th International Works hop on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu). ptpy)), tris (benzo [h] quinoline) iridium (Ir (bzq)), etc. (These metal complexes are generally called orthometallated iridium complexes.)
[0013] また、前記、 S. Lamansky et al.， J. Am. Chem. Soc.， 123卷， 4304ぺー ジ（2001年）等においても、各種イリジウム錯体を用いて素子化する試みがされてい る。 [0013] Further, as described in S. Lamansky et al., J. Am. Chem. Soc., Vol. 123, No. 4304- Di (2001) and the like have also attempted to make devices using various iridium complexes.
[0014] また、高い発光効率を得るために、 The 10th International Workshop on Inorganic and Organic Electroluminescence (EL' 00、浜松)では、 Ikai等 はホール輸送性の化合物を燐光性化合物のホストとして用いている。また、 M. E. T ompson等は、各種電子輸送性材料を燐光性化合物のホストとして、これらに新規な イリジウム錯体をドープして用いてレ、る。  [0014] In order to obtain high luminous efficiency, in the 10th International Workshop on Inorganic and Organic Electroluminescence (EL'00, Hamamatsu), Ikai and others use a hole transporting compound as a host of a phosphorescent compound. ME Tompson et al. Use various electron-transporting materials as a host of a phosphorescent compound and dope them with a novel iridium complex.
[0015] 中心金属をイリジウムの代わりに白金としたオノレトメタルイ匕錯体も注目されている。こ の種の錯体に関しては、配位子に特徴を持たせた例が多数知られている（例えば、 特許文献:!〜 5及び非特許文献 1参照。）。  [0015] Onoleto metal iodide complexes, in which the central metal is platinum instead of iridium, have also attracted attention. Regarding this type of complex, there are many known examples in which ligands are characterized (for example, see Patent Documents:! To 5 and Non-Patent Document 1).
[0016] 何れの場合も発光素子とした場合の発光輝度や発光効率は、その発光する光が燐 光に由来することから、従来の素子に比べ大幅に改良されるものであるが、素子の発 光寿命については従来の素子よりも低いという問題点があった。このように、りん光性 の高効率の発光材料は、発光波長の短波化と素子の発光寿命の改善が難しく実用 に耐えうる性能を十分に達成できてレ、なレ、のが現状である。  [0016] In any case, the light emission luminance and the light emission efficiency of the light emitting element are greatly improved as compared with the conventional element because the emitted light is derived from phosphorescence. There is a problem that the light emission lifetime is shorter than that of the conventional device. As described above, phosphorescent high-efficiency light-emitting materials are difficult to shorten the emission wavelength and improve the light-emitting life of the device, and can achieve sufficient performance for practical use. .
[0017] また、波長の短波化に関しては、これまでフエニルピリジンにフッ素原子、トリフルォ ロメチル基、シァノ基等の電子吸引基を置換基として導入すること、配位子としてピコ リン酸やビラザボール系の配位子を導入することが知られている（例えば、特許文献 6〜： 13及び非特許文献:!〜 4参照。）が、これらの配位子では発光材料の発光波長 が短波化して青色を達成し、高効率の素子を達成できる一方、素子の発光寿命は劣 化する傾向もみられ、そのトレードオフの改善が求められていた。  [0017] Regarding the shortening of the wavelength, an electron-withdrawing group such as a fluorine atom, a trifluoromethyl group or a cyano group has been introduced as a substituent into phenylpyridine, and picolinic acid or virazabole-based ligand has been used as a ligand. It is known to introduce a ligand (for example, see Patent Documents 6 to 13 and Non-Patent Documents:! To 4), but in these ligands, the emission wavelength of the light-emitting material is shortened. While blue can be achieved and a highly efficient device can be achieved, the emission lifetime of the device tends to be degraded, and improvement of the trade-off has been required.
特許文献 1 :特開 2002— 332291号公報  Patent Document 1: JP-A-2002-332291
特許文献 2 :特開 2002— 332292号公報  Patent Document 2: JP 2002-332292 A
特許文献 3 :特開 2002— 338588号公報  Patent Document 3: JP-A-2002-338588
特許文献 4 :特開 2002— 226495号公報  Patent Document 4: JP-A-2002-226495
特許文献 5：特開 2002— 234894号公報  Patent Document 5: Japanese Patent Application Laid-Open No. 2002-234894
特許文献 6 :国際公開第 02/15645号パンフレット  Patent Document 6: WO 02/15645 pamphlet
特許文献 7 :特開 2003— 123982号公報 特許文献 8 :特開 2002— 117978号公報 Patent Document 7: JP-A-2003-123982 Patent Document 8: Japanese Patent Application Laid-Open No. 2002-117978
特許文献 9 :特開 2003— 146996号公報  Patent Document 9: JP 2003-146996 A
特許文献 10 : Patent Document 10:
特許文献 11：国際公開第 05/007767号パンフレット  Patent Document 11: International Publication No. 05/007767 pamphlet
特許文献 12 :国際公開第 04/101707号パンフレット  Patent Document 12: WO 04/101707 pamphlet
特許文献 13 :特開 2005— 053912号公報  Patent Document 13: JP 2005-053912 A
非特許文献 1 : Inorganic Chemistry,第 41卷，第 12号， 3055〜3066ページ（2 002年）  Non-Patent Document 1: Inorganic Chemistry, Vol. 41, No. 12, pp. 3055-3066 (2002)
非特許文献 2 : Aplied Physics Letters,第 79卷， 2082ページ（2001年） 非特許文献 3 : Aplied Physics Letters,第 83卷， 3818ページ（2003年） 非特許文献 4 : New Journal of Chemistry,第 26卷， 1171ページ（2002年） 発明の開示  Non-Patent Document 2: Aplied Physics Letters, Vol. 79, page 2082 (2001) Non-Patent Document 3: Aplied Physics Letters, Vol. 83, page 3818 (2003) Non-Patent Document 4: New Journal of Chemistry, 26 Vol., P. 1171 (2002) Disclosure of the Invention
[0018] 本発明の目的は、発光波長が制御され、高い発光効率を示し、且つ、発光寿命の 長い有機 EL素子、照明装置及び表示装置を提供することである。  An object of the present invention is to provide an organic EL element, a lighting device, and a display device, in which the emission wavelength is controlled, which exhibits high luminous efficiency, and which has a long emission life.
[0019] 上記目的を達成するための、本発明の態様の一つは、下記一般式（1)または、該 一般式（1)の互変異性体を部分構造として有する金属錯体であることを特徴とする 有機エレクト口ルミネッセンス素子材料にある。 一般式 (1)  [0019] One embodiment of the present invention for achieving the above object is a metal complex having the following general formula (1) or a tautomer of the general formula (1) as a partial structure. It is a feature of the organic electroluminescent device material. General formula (1)
[0020] 〔式中、 Z11は、芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 R 、R 、R は、各々水素原子または置換基を表す。 M は、元素周期表 [In the formula, Z11 represents an atom group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. R 1, R 2 and R 3 each represent a hydrogen atom or a substituent. M is the periodic table of the elements
11 12 13 11  11 12 13 11
における 8族〜 10族の金属を表す。〕  Represents a metal belonging to Group 8 to Group 10. ]
図面の簡単な説明  Brief Description of Drawings
[0021] [図 1]有機 EL素子から構成される表示装置の一例を示した模式図である。 [図 2]表示部 Aの模式図である。 FIG. 1 is a schematic diagram showing an example of a display device including an organic EL element. FIG. 2 is a schematic diagram of a display unit A.
[図 3]画素を構成する駆動回路の等価回路図である。  FIG. 3 is an equivalent circuit diagram of a driving circuit constituting a pixel.
[図 4]パッシブマトリクス方式による表示装置の模式図である。  FIG. 4 is a schematic diagram of a display device using a passive matrix method.
[図 5]有機 EL素子 OLED1— 1の封止構造の概略模式図である。  FIG. 5 is a schematic diagram of a sealing structure of an organic EL element OLED1-1.
[図 6]有機 EL素子を具備してなる照明装置の模式図である。  FIG. 6 is a schematic diagram of a lighting device including an organic EL element.
発明を実施するための最良の形態  BEST MODE FOR CARRYING OUT THE INVENTION
[0022] 本発明の上記課題は、下記の構成：!〜 28により達成された。 [0022] The above object of the present invention has been achieved by the following configurations:! To 28.
(1) 下記一般式（1)または、該一般式（1)の互変異性体を部分構造として有する金 属錯体、下記一般式（2)または、該一般式（2)の互変異性体を部分構造として有す る金属錯体、下記一般式 (3)または、該一般式（3)の互変異性体を部分構造として 有する金属錯体、下記一般式 (4)または、該一般式 (4)の互変異性体を部分構造と して有する金属錯体、下記一般式 (5)または、該一般式 (5)の互変異性体を部分構 造として有する金属錯体、または、下記一般式 (6)または、該一般式 (6)の互変異性 体を部分構造として有する金属錯体であることを特徴とする有機エレクト口ルミネッセ ンス素子材料。  (1) A metal complex having the following general formula (1) or a tautomer of the general formula (1) as a partial structure, a tautomer of the following general formula (2) or the general formula (2) A metal complex having the following general formula (3) or a tautomer of the general formula (3) as a partial structure; a metal complex having the following general formula (4) or a general formula (4) ) As a partial structure, a metal complex having the following general formula (5) or a tautomer of the general formula (5) as a partial structure, or a metal complex having the following general formula ( 6) An organic electroluminescent device material characterized by being a metal complex having a tautomer of the general formula (6) as a partial structure.
[0023] [化 1] 般式 (1 ) [0023] [Formula 1] General formula (1)
[0024] 〔式中、 Z11は、芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 R 、R 、R は、各々水素原子または置換基を表す。 M は、元素周期表 [In the formula, Z11 represents an atom group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. R 1, R 2 and R 3 each represent a hydrogen atom or a substituent. M is the periodic table of the elements
11 12 13 11  11 12 13 11
における 8族〜 10族の金属を表す。〕  Represents a metal belonging to Group 8 to Group 10. ]
[0025] [化 2] 一般式 (2) [0025] General formula (2)
[0026] 〔式中、 Z21は芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 R 、 R 、 R は、各々水素原子または置換基を表す。 M は、元素周期表 [In the formula, Z21 represents an atom group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. R 1, R 2 and R 3 each represent a hydrogen atom or a substituent. M is the periodic table of the elements
21 22 23 21  21 22 23 21
における 8族〜 10族の金属を表す。〕  Represents a metal belonging to Group 8 to Group 10. ]
[0027] [化 3] 一般式 (3) [0027] [Formula 3] General formula (3)
[0028] 〔式中、 Z31は、芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 X 、 Χ 、 Χ は、各々置換基を有してもよい炭素原子または窒素原子を  [In the formula, Z31 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X, Χ and Χ each represent a carbon atom or a nitrogen atom which may have a substituent.
31 32 33  31 32 33
表すが、少なくとも 2つは、窒素原子または N (R ) （ここで、 Rは、水素原子また  Where at least two are nitrogen atoms or N (R) (where R is a hydrogen atom or
3 3  3 3
は置換基を表す。）を表す。 C は炭素原子を表す。 M は、元素周期表における 8族  Represents a substituent. ). C represents a carbon atom. M is group 8 in the periodic table
31 31  31 31
〜10族の金属を表す。 C と Nとの間の結合、 Nと X との間の結合、 X と X との間の  Represents a metal of Group 10 Bond between C and N, bond between N and X, between X and X
31 33 32 33 結合、 X と X との間の結合、 C と X との間の結合は、各々単結合または二重結合 31 33 32 33 bond, bond between X and X, bond between C and X are single bond or double bond, respectively
31 32 31 31 31 32 31 31
を表す。〕  Represents. ]
[0029] [化 4] 一般式 (4) [0029] [Formula 4] General formula (4)
Λ^-ι— X42 Λ ^ -ι— X 4 2
Ιί 'λ  Ιί 'λ
C43、 ,^C41 ：'文 C 43,, ^ C 41: ' statement
' Z41、ノ'  'Z41, No'
[0030] 〔式中、 Z41は、芳香族複素環を形成するのに必要な原子群を表す。 X 、X は置換 [In the formula, Z41 represents an atom group necessary for forming an aromatic heterocyclic ring. X and X are replaced
41 42 基を有してもよい炭素原子または窒素原子を表すが、その少なくとも 1つは、窒素原 子または— N (R ) - (ここで、 Rは、水素原子または置換基を表す。 )を表す。 M は  41 42 represents a carbon atom or a nitrogen atom which may have a group, at least one of which is a nitrogen atom or —N (R) — (where R represents a hydrogen atom or a substituent) Represents M is
4 4 41 4 4 41
、元素周期表における 8族〜 10族の金属を表す。 C 、C 、C は、各々炭素原子を Represents a metal belonging to Groups 8 to 10 of the periodic table. C 1, C 2 and C 3 each have a carbon atom
41 42 43  41 42 43
表す。 M は、元素周期表における 8族〜 10族の金属を表す。 C と C との間の結合  Represent. M represents a metal belonging to Groups 8 to 10 in the periodic table. Coupling between C and C
41 41 42  41 41 42
、C と X との間の結合、 X と X との間の結合、 X と C との間の結合、 C と C との , The bond between C and X, the bond between X and X, the bond between X and C, the bond between C and C
41 42 41 42 41 43 42 43 間の結合は、単結合または二重結合を表す。〕 The bond between 41 42 41 42 41 43 42 43 represents a single bond or a double bond. ]
[0031] [化 5] 一般式 (5)  [0031] [Formula 5] General formula (5)
[0032] 〔式中、 Z51は、芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 X は、酸素原子または硫黄原子を表す。 R 、R は、水素原子または置 [In the formula, Z51 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X represents an oxygen atom or a sulfur atom. R and R are a hydrogen atom or
51 51 52 換基を表す。 M は、元素周期表における 8族〜 10族の金属を表す。〕  51 51 52 represents a substituent. M represents a metal belonging to Groups 8 to 10 in the periodic table. ]
51  51
[0033] [化 6] 一般式 (6) [0033] [Formula 6] General formula (6)
Χ62一ズ63 〔式中、 Z61は、芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 X Χ Χ は、各々置換基を有してもよい炭素原子または窒素原子を Chi 62 Ichizu 63 wherein, Z61 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X Χ represents a carbon atom or a nitrogen atom, each of which may have a substituent.
61 62 63  61 62 63
表すが、少なくとも 1つは窒素原子を表す。 Μ は、元素周期表における 8族〜 10族 And at least one of them represents a nitrogen atom. Μ is group 8 to group 10 in the periodic table
61  61
の金属を表す。〕 Represents a metal. ]
(2) 上記一般式（1)または、該一般式 (1)の互変異性体を部分構造として有する金 属錯体であることを特徴とする前記（1)に記載の有機エレクト口ルミネッセンス素子材 料。  (2) The organic electroluminescent device material according to the above (1), which is a metal complex having the above general formula (1) or a tautomer of the general formula (1) as a partial structure. Fees.
(3) 上記一般式（1)または、該一般式 (1)の互変異性体を部分構造として有する金 属錯体において Z11が芳香族複素環を形成するのに必要な原子群を表すことを特 徴とする前記（2)に記載の有機エレクト口ルミネッセンス素子材料。  (3) In a metal complex having the above general formula (1) or a tautomer of the general formula (1) as a partial structure, Z11 represents an atomic group necessary for forming an aromatic heterocyclic ring. The organic electroluminescent device material according to (2), which is characterized by the above-mentioned (2).
(4) 上記一般式 (2)または、該一般式 (2)の互変異性体を部分構造として有する金 属錯体であることを特徴とする前記（1)に記載の有機エレクト口ルミネッセンス素子材 料。  (4) The organic electroluminescent device material according to the above (1), which is a metal complex having the above-mentioned general formula (2) or a tautomer of the general formula (2) as a partial structure. Fees.
(5) 上記一般式 (3)または、該一般式 (3)の互変異性体を部分構造として有する金 属錯体であることを特徴とする前記（1)に記載の有機エレクト口ルミネッセンス素子材 料。  (5) The organic electroluminescent device material according to the above (1), which is a metal complex having the above-mentioned general formula (3) or a tautomer of the general formula (3) as a partial structure. Fees.
(6) 上記一般式（3)または、該一般式 (3)の互変異性体を部分構造として有する金 属錯体において、 X は置換基を有してもよい炭素原子を表し、 X Χ は窒素原子  (6) In the above-mentioned general formula (3) or a metal complex having a tautomer of the general formula (3) as a partial structure, X represents a carbon atom which may have a substituent, and XΧ represents Nitrogen atom
31 32 33  31 32 33
又は N (R ) （ここで、 Rは、水素原子または置換基を表す。）を表すことを特徴と Or N (R) (where R represents a hydrogen atom or a substituent).
3 3  3 3
する前記（5)に記載の有機エレクト口ルミネッセンス素子材料。 (5) The organic electroluminescent device material according to (5) above.
(7) 上記一般式 (4)または、該一般式 (4)の互変異性体を部分構造として有する金 属錯体であることを特徴とする前記（1)に記載の有機エレクト口ルミネッセンス素子材 料。 (7) The organic electroluminescent device according to the above (1), which is a metal complex having the above general formula (4) or a tautomer of the general formula (4) as a partial structure. Fees.
(8) 上記一般式（5)または、該一般式 (5)の互変異性体を部分構造として有する金 属錯体であることを特徴とする前記（1)に記載の有機エレクト口ルミネッセンス素子材 料。  (8) The organic electroluminescent device according to the above (1), which is a metal complex having the above general formula (5) or a tautomer of the general formula (5) as a partial structure. Fees.
(9) 上記一般式 (5)または、該一般式 (5)の互変異性体を部分構造として有する金 属錯体において X 、硫黄原子を表すことを特徴とする前記 (8)に記載の有機エレ  (9) The organic compound according to (8), wherein in the metal complex having the tautomer of the general formula (5) or the tautomer of the general formula (5) as a partial structure, X represents a sulfur atom. Ele
51  51
タトロルミネッセンス素子材料。 Tatrol luminescence element material.
(10) 上記一般式 (6)または、該一般式 (6)の互変異性体を部分構造として有する 金属錯体であることを特徴とする前記（1)に記載の有機エレクト口ルミネッセンス素子 材料。  (10) The organic electroluminescent device material according to the above (1), which is a metal complex having the above general formula (6) or a tautomer of the general formula (6) as a partial structure.
(11) 上記一般式 (6)または、該一般式 (6)の互変異性体を部分構造として有する 金属錯体において、 X 、χ の少なくとも 1つは窒素原子を表すことを特徴とする前  (11) The above-mentioned general formula (6) or a metal complex having a tautomer of the general formula (6) as a partial structure, wherein at least one of X and χ represents a nitrogen atom.
61 63  61 63
記（10)に記載の有機エレクト口ルミネッセンス素子材料。 The organic electroluminescent device material according to (10).
(12) 前記一般式（1)において、 M 力 S、イリジウムまたは白金であることを特徴とす  (12) In the general formula (1), M is S, iridium or platinum.
11  11
る前記（2)に記載の有機エレクト口ルミネッセンス素子材料。 The organic electroluminescent device material according to (2) above.
(13) 上記一般式（1)において Z11が芳香族複素環を形成するのに必要な原子群 を表すことを特徴とする前記（12)に記載の有機エレクト口ルミネッセンス素子材料。 (13) The organic electroluminescent device material according to the above (12), wherein in the general formula (1), Z11 represents an atomic group necessary for forming an aromatic heterocyclic ring.
(14) 前記一般式（2)において、 M 力 S、イリジウムまたは白金であることを特徴とす (14) In the general formula (2), M is S, iridium or platinum.
21  twenty one
る前記 (4)に記載の有機エレクト口ルミネッセンス素子材料。 (4) The organic electroluminescent device material according to (4) above.
(15) 前記一般式（3)において、 M 力 S、イリジウムまたは白金であることを特徴とす  (15) In the general formula (3), M is S, iridium or platinum.
31  31
る前記（5)に記載の有機エレクト口ルミネッセンス素子材料。 The organic electroluminescent device material according to (5) above.
(16) 上記一般式（3)において、 X は置換基を有してもよい炭素原子を表し、 X 、  (16) In the above general formula (3), X represents a carbon atom which may have a substituent;
31 32 31 32
X は窒素原子又は— N (R ) - (ここで、 Rは、水素原子または置換基を表す。）を表X represents a nitrogen atom or —N (R) — (where R represents a hydrogen atom or a substituent).
33 3 3 33 3 3
すことを特徴とする前記（15)に記載の有機エレクト口ルミネッセンス素子材料。The organic electroluminescent device material according to (15), wherein:
(17) 前記一般式 (4)において、 M 力 イリジウムまたは白金であることを特徴とす (17) In the general formula (4), M is iridium or platinum.
41  41
る前記（7)に記載の有機エレクト口ルミネッセンス素子材料。 The organic electroluminescent device material according to the above (7), wherein
(18) 前記一般式（5)において、 M 力 イリジウムまたは白金であることを特徴とす  (18) In the general formula (5), M is iridium or platinum.
51  51
る前記（8)に記載の有機エレクト口ルミネッセンス素子材料。 (19) 上記一般式（5)において X 力 S、硫黄原子を表すことを特徴とする前記（18) The organic electroluminescent device material according to (8) above. (19) The above (18), wherein in the general formula (5), X represents S and a sulfur atom is represented.
51  51
に記載の有機エレクト口ルミネッセンス素子材料。 4. The organic electroluminescent device material according to item 1.
(20) 前記一般式（6)において、 M 力 S、イリジウムまたは白金であることを特徴とす  (20) In the general formula (6), M is S, iridium or platinum.
61  61
る前記（10)に記載の有機エレクト口ルミネッセンス素子材料。 The organic electroluminescent device material according to the above (10).
(21) 上記一般式（6)において、 X 、X の少なくとも 1つは窒素原子を表すことを  (21) In the general formula (6), at least one of X 1 and X 2 represents a nitrogen atom.
61 63  61 63
特徴とする前記（20)に記載の有機エレクト口ルミネッセンス素子材料。 The organic electroluminescent device material according to (20), which is characterized in that it is characterized in that:
(22) 前記（1)〜（21)のいずれか 1項に記載の有機エレクト口ルミネッセンス素子材 料を含有することを特徴とする有機エレクト口ルミネッセンス素子。  (22) An organic electroluminescent device comprising the organic electroluminescent device according to any one of (1) to (21).
(23) 構成層として発光層を有し、該発光層が前記（1)〜（21)のいずれか 1項に記 載の有機エレクト口ルミネッセンス素子材料を含有することを特徴とする前記（22)に 記載の有機エレクト口ルミネッセンス素子。  (23) The light-emitting device according to (22), further including a light-emitting layer as a constituent layer, wherein the light-emitting layer contains the organic electroluminescent device material described in any one of (1) to (21). ). The organic electroluminescent device according to 2).
(24) 構成層として正孔阻止層を有し、該正孔阻止層が前記（1)〜（21)のいずれ 力 1項に記載の有機エレクト口ルミネッセンス素子材料を含有することを特徴とする前 記（22)または（23)に記載の有機エレクト口ルミネッセンス素子。  (24) A hole blocking layer as a constituent layer, wherein the hole blocking layer contains the organic electroluminescent device material according to any one of (1) to (21). The organic electroluminescent device according to the above (22) or (23).
(25) 構成層として発光層を有し、該発光層が、カルボリン誘導体または該カルボリ ン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが窒素 原子で置換されている環構造を有する誘導体を含有することを特徴とする前記（22) 〜（24)の何れ力 1項に記載の有機エレクト口ルミネッセンス素子。  (25) A light-emitting layer as a constituent layer, wherein the light-emitting layer has a ring structure in which at least one of carbon atoms of a carboline derivative or a hydrocarbon ring constituting a carboline ring of the carboline derivative is substituted with a nitrogen atom. 2. The organic electroluminescent device according to any one of the above (22) to (24), further comprising a derivative having the compound.
(26) 構成層として正孔阻止層を有し、該正孔阻止層が、カルボリン誘導体または 該カルボリン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも 一つが窒素原子で置換されている環構造を有する誘導体を含有することを特徴とす る前記（22)〜（25)の何れ力 4項に記載の有機エレクト口ルミネッセンス素子。  (26) a hole blocking layer as a constituent layer, wherein the hole blocking layer has at least one carbon atom of a carboline derivative or a hydrocarbon ring constituting a carboline ring of the carboline derivative substituted with a nitrogen atom. 5. The organic electroluminescent device according to any one of the above items (22) to (25), further comprising a derivative having a ring structure.
(27) 前記（22)〜（26)の何れ力、 1項に記載の有機エレクト口ルミネッセンス素子を 有することを特徴とする表示装置。  (27) A display device comprising the organic electorescence luminescent element according to any one of (22) to (26).
(28) 前記（22)〜（26)の何れ力、 1項に記載の有機エレクト口ルミネッセンス素子を 有することを特徴とする照明装置。  (28) A lighting device comprising the organic electorophore luminescent element according to any one of (22) to (26).
本発明の有機 EL素子材料においては、前記（1)〜（21)のいずれか 1項に規定さ れる構成により、有機 EL素子用に有用な有機 EL素子材料を分子設計することに成 功した。また、該有機 EL素子材料を用いることにより、高い発光効率を示し、且つ、 発光寿命の長い有機 EL素子、照明装置及び表示装置を提供することができた。 In the organic EL device material of the present invention, the composition defined in any one of the above (1) to (21) is used to molecularly design an organic EL device material useful for an organic EL device. It worked. Further, by using the organic EL element material, it was possible to provide an organic EL element, a lighting device, and a display device exhibiting high luminous efficiency and having a long luminous life.
[0036] 本発明者等は、上記の問題点について鋭意検討を行った結果、金属錯体の配位 子として一般的に使用されているフエ二ルビリジン (6員環と 6員環が炭素—炭素結合 で結ばれてレ、るもの）の母核を、前記一般式（1)〜（6)で各々表されるような「芳香族 炭化水素環、または、芳香族複素環 (好ましくは 6員環)」と「芳香族複素環 (好ましく は 5員環)」、が炭素一炭素結合、または、炭素一窒素結合で結ばれたような、特定 の部分構造を有する金属錯体を有機 EL素子材料として含む有機 EL素子により、従 来の青色用の金属錯体、特に電子吸引基によってのみ発光波長を短波側に制御し てきた有機 EL素子材料を用いて作製された有機 EL素子の問題点であった発光寿 命が大幅に改善されることを見出した。  [0036] The present inventors have conducted intensive studies on the above-mentioned problems, and as a result, have found that phenylviridine (a 6-membered ring and a 6-membered The mother nucleus of the compound represented by the general formulas (1) to (6) is represented by an aromatic hydrocarbon ring or an aromatic heterocyclic ring (preferably 6-membered). Ring) and an aromatic heterocyclic ring (preferably a 5-membered ring) are connected by a carbon-carbon bond or a carbon-nitrogen bond to form a metal complex having a specific partial structure. This is a problem of an organic EL device manufactured using a conventional metal complex for blue, especially an organic EL device material whose emission wavelength is controlled to a shorter wavelength only by an electron-withdrawing group. It was found that the luminous life was greatly improved.
[0037] また、置換基自身の発光波長が長波なものを置換基として導入することにより、金 属錯体の発光波長を長波な領域に制御する機能を付与する為の分子設計は、本発 明に係る、一般式（1)〜（6)または、該一般式（1)〜（6)の各々の互変異性体の基 本骨格を出発点にすることにより適切な部分構造を選択することが可能である。  [0037] Further, the present invention provides a molecular design for imparting a function of controlling the emission wavelength of a metal complex to a long-wave region by introducing a substituent having a long-wavelength emission wavelength as a substituent. The selection of an appropriate partial structure by using the basic skeleton of the general formulas (1) to (6) or each tautomer of the general formulas (1) to (6) as a starting point. Is possible.
[0038] 以下、本発明に係る各構成要素の詳細について、順次説明する。  Hereinafter, details of each component according to the present invention will be sequentially described.
[0039] 《金属錯体》  [0039] << Metal complex >>
本発明の有機 EL素子材料に係る金属錯体について説明する。  The metal complex according to the organic EL device material of the present invention will be described.
[0040] 本発明に係る、一般式（1)〜（6)または該一般式（1)〜（6)の各々の互変異性体 を部分構造として有する金属錯体の含有層としては、発光層及び/または正孔阻止 層が好ましぐまた、発光層に含有する場合は、発光層中の発光ドーパントとして用 レ、ることにより、本発明の有機 EL素子の外部取り出し量子効率の効率アップ（高輝 度化）や発光寿命の長寿命化を達成することができる。  [0040] As a layer containing a metal complex having a partial structure of the general formulas (1) to (6) or each of the tautomers of the general formulas (1) to (6) according to the present invention, a light emitting layer And / or a hole-blocking layer is preferred. When the compound is contained in the light-emitting layer, it can be used as a light-emitting dopant in the light-emitting layer to increase the efficiency of the external extraction quantum efficiency of the organic EL device of the present invention ( (Higher brightness) and a longer luminescent life.
[0041] 《一般式（1)または該一般式（1)の互変異性体》  [0041] << General formula (1) or tautomer of general formula (1) >>
一般式（1)または該一般式（1)の互変異性体において、 Z11で表される芳香族炭 化水素環としては、ベンゼン環、ビフエニル環、ナフタレン環、ァズレン環、アントラセ ン環、フエナントレン環、ピレン環、タリセン環、ナフタセン環、トリフエ二レン環、 o—テ ルフエ二ル環、 m—テルフエニル環、 p—テルフエニル環、ァセナフテン環、コロネン 環、フルオレン環、フルオラントレン環、ナフタセン環、ペンタセン環、ペリレン環、ぺ ンタフェン環、ピセン環、ピレン環、ピラントレン環、アンスラアントレン環等が挙げられ る。 In the general formula (1) or a tautomer of the general formula (1), the aromatic hydrocarbon ring represented by Z11 includes a benzene ring, a biphenyl ring, a naphthalene ring, an azulene ring, an anthracene ring, and a phenanthrene ring. Ring, pyrene ring, thalicene ring, naphthacene ring, triphenylene ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene Ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring, pyrene ring, pyranthrene ring, anthranthrene ring and the like.
[0042] 中でも好ましく用いられるのは、ベンゼン環である。更に、前記芳香族炭化水素環 は、後述する、前記一般式（1)において R 、R 、R で各々表される置換基を有して  [0042] Among them, a benzene ring is preferably used. Further, the aromatic hydrocarbon ring has a substituent represented by R 1, R 2, R 3 in the general formula (1) described below.
11 12 13  11 12 13
あよい。  Oh good.
[0043] 一般式（1)または該一般式（1)の互変異性体において、 Z11で表される芳香族複 素環としては、フラン環、チォフェン環、ピリジン環、ピリダジン環、ピリミジン環、ピラジ ン環、トリアジン環、ベンゾイミダゾール環、ォキサジァゾール環、トリァゾール環、イミ ダゾール環、ピラゾール環、チアゾール環、インドール環、ベンゾイミダゾール環、ベ ンゾチアゾール環、ベンゾォキサゾール環、キノキサリン環、キナゾリン環、フタラジン 環、力ルバゾール環、カルボリン環、カルボリン環を構成する炭化水素環の炭素原子 の少なくともひとつが更に窒素原子で置換されている環等が挙げられる。  In the general formula (1) or a tautomer of the general formula (1), the aromatic complex ring represented by Z11 includes a furan ring, a thiophene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, Pyrazine ring, triazine ring, benzimidazole ring, oxaziazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, Examples include a phthalazine ring, a carbazole ring, a carboline ring, and a ring in which at least one of carbon atoms of a hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom.
[0044] 中でも好ましいのは、ピリジン環である。更に、前記芳香族複素環は、後述する、前 記一般式（1)において R 、R 、R で各々表される置換基を有してもよい。  [0044] Among them, a pyridine ring is preferable. Further, the aromatic heterocyclic ring may have a substituent represented by R 1, R 2 and R 3 in the above-mentioned general formula (1).
11 12 13  11 12 13
[0045] 一般式（1)または該一般式（1)の互変異性体において、 R11で表される環は芳香 族複素環であることが好ましい。本発明の一般式（1)の部分構造として含まれている ような 5員の複素環が、分子内に含有されている場合、それに連結する芳香族環（本 発明では Z11に相当する）は、芳香族複素環である方が、分子の安定性が向上し、 発光波長がより短波長となる。  In the general formula (1) or a tautomer of the general formula (1), the ring represented by R11 is preferably an aromatic heterocyclic ring. When a 5-membered heterocyclic ring such as that contained in the partial structure of the general formula (1) of the present invention is contained in the molecule, the aromatic ring (corresponding to Z11 in the present invention) linked thereto is In the case of an aromatic heterocycle, the stability of the molecule is improved, and the emission wavelength is shorter.
[0046] 一般式（1)または該一般式（1)の互変異性体において R 、R 、R で各々表され  In the general formula (1) or a tautomer of the general formula (1), each is represented by R 1, R 2, and R 3.
11 12 13  11 12 13
る置換基としては、例えば、アルキル基 (例えば、メチル基、ェチル基、イソプロピノレ 基、ヒドロキシェチル基、メトキシメチノレ基、トリフルォロメチル基、 t_ブチル基等）、シ クロアルキル基（例えば、シクロペンチル基、シクロへキシル基等）、ァラルキル基（例 えば、ベンジノレ基、 2—フエネチル基等）、芳香族炭化水素基 (例えば、フエニル基、 p—クロロフヱニル基、メシチル基、トリル基、キシリル基、ビフヱ二リル基、ナフチル基 、アントリル基、フエナントリル基等）、芳香族複素環基 (例えば、フリル基、チェニル 基、ピリジノレ基、ピリダジニル基、ピリミジニル基、ピラジュル基、トリアジニル基、イミダ ゾリル基、ピラゾリル基、チアゾリル基、キナゾリニル基、カルバゾリル基、カルボリニル 基、ジァザカルバゾリル基（ジァザカルバゾリル基とは、該カルボリニル基のカルボリ ン環を構成する炭素原子の任意にひとつが窒素原子で置換されたものを示す。）、フ タラジニル基等）、アルコキシル基（例えば、エトキシ基、イソプロポキシ基、ブトキシ基 等）、ァリールォキシ基 (例えば、フエノキシ基、ナフチルォキシ基等）、シァノ基、水 酸基、アルケニル基 (例えば、ビュル基等）、スチリル基、ハロゲン原子 (例えば、塩素 原子、臭素原子、沃素原子、フッ素原子等）等が挙げられる。これらの基は、更に置 換されていてもよい。 Examples of the substituent include, for example, an alkyl group (for example, a methyl group, an ethyl group, an isopropylinole group, a hydroxyethyl group, a methoxymethinole group, a trifluoromethyl group, a t_butyl group, etc.), a cycloalkyl group (for example, , A cyclopentyl group, a cyclohexyl group, etc.), an aralkyl group (eg, a benzyl group, a 2-phenyl group, etc.), an aromatic hydrocarbon group (eg, a phenyl group, a p-chlorophenyl group, a mesityl group, a tolyl group, a xylyl group) Group, biphenylyl group, naphthyl group, anthryl group, phenanthryl group, etc.), aromatic heterocyclic group (for example, furyl group, chenyl group, pyridinole group, pyridazinyl group, pyrimidinyl group, pyrazuryl group, triazinyl group, imida Zolyl group, pyrazolyl group, thiazolyl group, quinazolinyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (the diazacarbazolyl group is any of the carbon atoms constituting the carbolin ring of the carbolinyl group) Are substituted with a nitrogen atom.), Phthalazinyl group, etc.), alkoxyl group (eg, ethoxy group, isopropoxy group, butoxy group, etc.), aryloxy group (eg, phenoxy group, naphthyloxy group, etc.) , A cyano group, a hydroxyl group, an alkenyl group (eg, a butyl group), a styryl group, a halogen atom (eg, a chlorine atom, a bromine atom, an iodine atom, a fluorine atom, etc.). These groups may be further substituted.
[0047] 中でも、本発明では、上記 R 、 R 、 R で表される基の少なくともひとつは、上記の  Among them, in the present invention, at least one of the groups represented by R 1, R 2 and R 3 is
11 12 13  11 12 13
芳香族炭化水素基または芳香族複素環基であることが好ましい。  It is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group.
[0048] 一般式（1)または該一般式（1)の互変異性体において、 M は、元素周期表にお  In the general formula (1) or a tautomer of the general formula (1), M is
11  11
ける 8族〜 10族の金属（金属原子でも、イオンでもよい）を表す力 中でも好ましく用 レ、られるのは、白金 (Pt)とイリジウム（Ir)である。また、一般式（1)または該一般式（1 )の互辺異性体を部分構造として有する金属錯体において、 M は、金属でもよぐィ  Platinum (Pt) and iridium (Ir) are preferably used among the powers representing metals of group 8 to 10 (which may be metal atoms or ions). In the metal complex having the general formula (1) or an isomer of the general formula (1) as a partial structure, M may be a metal.
11  11
オンでもよレ、。  You can turn it on.
[0049] 本発明では、上記一般式（1)または該一般式（1)の互変異性体と M で表される中  In the present invention, the above-described general formula (1) or a tautomer of the general formula (1) and M
11  11
心金属（金属でもイオンでもよい）との間で配位結合が形成 (錯形成ともいう）されて金 属錯体が形成される。  A coordination bond is formed (also called complex formation) with a core metal (which may be a metal or an ion) to form a metal complex.
[0050] 《一般式（2)または該一般式（2)の互変異性体》  [0050] << General formula (2) or tautomer of general formula (2) >>
一般式（2)または該一般式（2)の互変異性体において、 Z21で表される芳香族炭 化水素環は、一般式（1)または該一般式（1)の互変異性体において、 Z11で表され る芳香族炭化水素環と同義である。  In the general formula (2) or the tautomer of the general formula (2), the aromatic hydrocarbon ring represented by Z21 is the same as the general formula (1) or the tautomer of the general formula (1). Has the same meaning as the aromatic hydrocarbon ring represented by Z11.
[0051] 一般式（2)または該一般式（2)の互変異性体において、 Z21で表される芳香族複 素環は、一般式（1)または該一般式（1)の互変異性体において、 Z11で表される芳 香族複素環と同義である。 In the general formula (2) or the tautomer of the general formula (2), the aromatic complex ring represented by Z21 is the same as the general formula (1) or the tautomer of the general formula (1). In the body, it has the same meaning as the aromatic heterocyclic ring represented by Z11.
[0052] 一般式（2)または該一般式（2)の互変異性体において、 R 、R 、R で、各々表さ In the general formula (2) or the tautomer of the general formula (2), R 1, R 2 and R 3 are each represented by
21 22 23  21 22 23
れる置換基は、一般式（1)または該一般式（1)の互変異性体において R 、R 、R  Substituents represented by R 1, R 2, R 3 in the general formula (1) or a tautomer of the general formula (1)
11 12 13 で各々表される置換基と同義である。 [0053] 一般式（2)または該一般式（2)の互変異性体において、 M で表される、元素周期 It has the same meaning as the substituents respectively represented by 11 12 13. [0053] In the general formula (2) or a tautomer of the general formula (2), an element period represented by M
21  twenty one
表における 8族〜 10族の金属（イオンでもよい）は、一般式（1)または該一般式（1) の互変異性体において、 M で表される、元素周期表における 8族〜 10族の金属と  The metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1). Metal and
11  11
同義である。  Synonymous.
[0054] 《一般式 (3)または該一般式 (3)の互変異性体》  [0054] << General formula (3) or a tautomer of the general formula (3) >>
一般式（3)または該一般式（3)の互変異性体において、 Z31で表される芳香族炭 化水素環は、一般式（1)または該一般式（1)の互変異性体において、 Z11で表され る芳香族炭化水素環と同義である。  In the general formula (3) or the tautomer of the general formula (3), the aromatic hydrocarbon ring represented by Z31 is the same as the general formula (1) or the tautomer of the general formula (1). Has the same meaning as the aromatic hydrocarbon ring represented by Z11.
[0055] 一般式（3)または該一般式（3)の互変異性体において、 Z31で表される芳香族複 素環は、一般式（1)または該一般式（1)の互変異性体において、 Z11で表される芳 香族複素環と同義である。 [0055] In the general formula (3) or the tautomer of the general formula (3), the aromatic complex ring represented by Z31 is the same as the general formula (1) or the tautomer of the general formula (1). In the body, it has the same meaning as the aromatic heterocyclic ring represented by Z11.
[0056] 一般式（3)または該一般式（3)の互変異性体において、 X 、X 、X で各々表さ In the general formula (3) or a tautomer of the general formula (3), each is represented by X 1, X 2 and X 3
31 32 33  31 32 33
れるー N (R ) の Rで表される置換基は、一般式（1)または該一般式（1)の互変異  The substituent represented by R in N (R) is a group represented by the general formula (1) or a tautomer of the general formula (1).
3 3  3 3
性体において R 、R 、R で各々表される置換基と同義である。  It has the same meaning as the substituents represented by R 1, R 2 and R 3 in the sexual form.
11 12 13  11 12 13
[0057] 一般式（3)または該一般式（3)の互変異性体において、 M で表される、元素周期  In the general formula (3) or a tautomer of the general formula (3), an element period represented by M
31  31
表における 8族〜 10族の金属（イオンでもよい）は、一般式（1)または該一般式（1) の互変異性体において、 M で表される、元素周期表における 8族〜 10族の金属と  The metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1). Metal and
11  11
同義である。  Synonymous.
[0058] 一般式（3)または該一般式（3)の互変異性体において、 X は置換基を有してもよ  In the general formula (3) or a tautomer of the general formula (3), X may have a substituent.
31  31
い炭素原子であり、 X 、X は窒素原子又は N (R ) （ここで、 Rは、水素原子ま  X and X are nitrogen atoms or N (R) (where R is hydrogen atom or
32 33 3 3  32 33 3 3
たは置換基を表す。）であることが好ましい。これにより、発光波長がより短波長となり Or a substituent. ) Is preferable. This makes the emission wavelength shorter
、また、合成の容易性が向上する。 Also, the ease of synthesis is improved.
[0059] 《一般式 (4)または該一般式 (4)の互変異性体》 [0059] << General formula (4) or a tautomer of the general formula (4) >>
一般式 (4)または該一般式 (4)の互変異性体において、 Z41で表される芳香族複 素環は、一般式（1)または該一般式（1)の互変異性体において、 Z11で表される芳 香族複素環と同義である。  In the general formula (4) or the tautomer of the general formula (4), the aromatic complex ring represented by Z41 is represented by the general formula (1) or the tautomer of the general formula (1): It has the same meaning as the aromatic heterocyclic ring represented by Z11.
[0060] 一般式 (4)または該一般式 (4)の互変異性体において、 X , X で各々表される— In the general formula (4) or a tautomer of the general formula (4), each represented by X 1 and X 2 —
41 42  41 42
N (R ) _の Rで表される置換基は、一般式（1)または該一般式（1)の互変異性体に おいて R 、R 、R で各々表される置換基と同義である。 The substituent represented by R of N (R) _ is represented by the general formula (1) or a tautomer of the general formula (1). Has the same meaning as the substituents represented by R 1, R 2 and R 3.
11 12 13  11 12 13
[0061] 一般式 (4)または該一般式 (4)の互変異性体において、 M で表される、元素周期  [0061] In the general formula (4) or a tautomer of the general formula (4), an element period represented by M
41  41
表における 8族〜 10族の金属（イオンでもよい）は、一般式（1)または該一般式（1) の互変異性体において、 M で表される、元素周期表における 8族〜 10族の金属と  The metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1). Metal and
11  11
同義である。  Synonymous.
[0062] 《一般式 (5)または該一般式 (5)の互変異性体》  [0062] << General formula (5) or a tautomer of the general formula (5) >>
一般式（5)または該一般式（5)の互変異性体において、 Z51で表される芳香族炭 化水素環は、一般式（1)または該一般式（1)の互変異性体において、 Z11で表され る芳香族炭化水素環と同義である。  In the general formula (5) or the tautomer of the general formula (5), the aromatic hydrocarbon ring represented by Z51 is the same as the general formula (1) or the tautomer of the general formula (1). Has the same meaning as the aromatic hydrocarbon ring represented by Z11.
[0063] 一般式（5)または該一般式（5)の互変異性体において、 Z51で表される芳香族複 素環は、一般式（1)または該一般式（1)の互変異性体において、 Z11で表される芳 香族複素環と同義である。 In the general formula (5) or the tautomer of the general formula (5), the aromatic complex ring represented by Z51 is the same as the general formula (1) or the tautomer of the general formula (1). In the body, it has the same meaning as the aromatic heterocyclic ring represented by Z11.
[0064] 一般式（5)または該一般式（5)の互変異性体において、 R 、R で各々表される置 In the general formula (5) or a tautomer of the general formula (5),
51 52  51 52
換基は、一般式（1)または該一般式（1)の互変異性体において R 、R 、R で各々  The substituents are each represented by R 1, R 2 and R 3 in the general formula (1) or a tautomer of the general formula (1).
11 12 13 表される置換基と同義である。  11 12 13 has the same meaning as the substituent represented.
[0065] 一般式（5)または該一般式（5)の互変異性体において、 M で表される、元素周期 [0065] In the general formula (5) or a tautomer of the general formula (5), an element period represented by M
51  51
表における 8族〜 10族の金属（イオンでもよい）は、一般式（1)または該一般式（1) の互変異性体において、 M で表される、元素周期表における 8族〜 10族の金属と  The metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1). Metal and
11  11
同義である。  Synonymous.
[0066] 一般式（5)または該一般式（5)の互変異性体において、 X は硫黄原子であること  In the general formula (5) or a tautomer of the general formula (5), X is a sulfur atom
51  51
が好ましい。一般に、ォキサゾール誘導体は、分子内開環を起こしやすく不安定であ ることが知られている。本発明の一般式（5)では、それが大きく改善されてはいるもの の、チアゾール誘導体である方が分子はより安定である。  Is preferred. In general, it is known that oxazole derivatives are liable to cause intramolecular ring opening and are unstable. In the general formula (5) of the present invention, although it is greatly improved, the molecule is more stable when it is a thiazole derivative.
[0067] 《一般式 (6)または該一般式 (6)の互変異性体》 [0067] << General formula (6) or a tautomer of the general formula (6) >>
一般式 (6)または該一般式 (6)の互変異性体において、 Z61で表される芳香族炭 化水素環は、一般式（1)または該一般式（1)の互変異性体において、 Z11で表され る芳香族炭化水素環と同義である。  In the general formula (6) or the tautomer of the general formula (6), the aromatic hydrocarbon ring represented by Z61 is the same as the general formula (1) or the tautomer of the general formula (1). Has the same meaning as the aromatic hydrocarbon ring represented by Z11.
[0068] 一般式（6)または該一般式（6)の互変異性体において、 Z61で表される芳香族複 素環は、一般式（1)または該一般式（1)の互変異性体において、 Z11で表される芳 香族複素環と同義である。 In the general formula (6) or a tautomer of the general formula (6), an aromatic compound represented by Z61 The prime ring has the same meaning as that of the aromatic heterocyclic ring represented by Z11 in the general formula (1) or a tautomer of the general formula (1).
[0069] 一般式（6)または該一般式（6)の互変異性体において、 M で表される、元素周期  [0069] In the general formula (6) or a tautomer of the general formula (6), an element period represented by M
61  61
表における 8族〜 10族の金属（イオンでもよい）は、一般式（1)または該一般式（1) の互変異性体において、 M で表される、元素周期表における 8族〜 10族の金属と  The metals belonging to groups 8 to 10 in the table (which may be ions) are represented by M in the general formula (1) or a tautomer of the general formula (1). Metal and
11  11
同義である。  Synonymous.
[0070] 一般式（6)または該一般式（6)の互変異性体において、 X 、X の少なくとも 1つが  In the general formula (6) or a tautomer of the general formula (6), at least one of X 1 and X 2 is
61 63  61 63
窒素原子であることが好ましい。これにより、発光波長がより短波長となり、また、合成 の容易性が向上する。  It is preferably a nitrogen atom. As a result, the emission wavelength becomes shorter, and the ease of synthesis is improved.
[0071] 以下、本発明に係る、前記一般式（1)〜（6)または該一般式（1)〜（6)の各々の互 変異性体を部分構造として有する金属錯体の具体例を示すが、本発明はこれらに限 定されない。  [0071] Hereinafter, specific examples of the metal complex according to the present invention having the above-mentioned general formulas (1) to (6) or the tautomers of the general formulas (1) to (6) as a partial structure are shown. However, the present invention is not limited to these.
[0072] [化 7] [0072]
[0073] [化 8] [0073]
〔皇 7ΐ寸 (Emperor 7 inch
u0076o u0076o
[0077] [化 11] Zl^ [8Z00] [0077] Zl ^ [8Z00]
[0079] [化 13] [0079]
[0080] [化 14] [0080]
a0081 l a0081 l
soo soo
[0083] [化 17] [0083] [Formula 17]
[8ΐ^>] [ 800] [8ΐ ^>] [800]
本発明の有機 EL素子材料に係る金属錯体は、例えば〇rganic Le 誌、 vol3 、 No. 16、 p2579〜2581 (2001)、 Inorganic Chemistry,第 30卷、第 8号 16 85〜： 1687ページ（1991年）、】. Am. Chem. Soc. , 123卷、 4304ページ（2001 年）、 Inorganic Chemistry,第 40卷、第 7号、 1704〜1711ページ（2001年）、 I norganic Chemistry,第 41卷、第 12号、 3055〜3066ページ（2002年）、 New Journal of Chemistry. ,第 26卷、 1171ページ（2002年）、更に、これらの文 献中に記載の参考文献等の方法を適用することにより合成できる。 The metal complex according to the organic EL device material of the present invention is described in, for example, 〇rganic Le magazine, vol3 , No. 16, p2579 to 2581 (2001), Inorganic Chemistry, Vol . 30, Vol . 85 ~: 1687 (1991),]. Am. Chem. Soc., 123, 4304 (2001), Inorganic Chemistry, 40, 7, 7, 1704-1711 (2001), I norganic Chemistry, Vol. 41, No. 12, pp. 3055-3066 (2002), New Journal of Chemistry., Vol. 26, pp. 1171 (2002), and references cited in these documents Can be synthesized by applying the above method.
[0086] 《金属錯体を含む有機 EL素子材料の有機 EL素子への適用》 [0086] << Application of organic EL device material containing metal complex to organic EL device >>
本発明の有機 EL素子材料を用いて、有機 EL素子を作製する場合、有機 EL素子 の構成層（詳細は後述する）の中で、発光層または正孔阻止層に用いることが好まし レ、。また、発光層中では、発光ドーパントとして好ましく用いられる。  When an organic EL device is produced using the organic EL device material of the present invention, it is preferable to use the organic EL device as a light emitting layer or a hole blocking layer among constituent layers of the organic EL device (details will be described later). . In the light emitting layer, it is preferably used as a light emitting dopant.
[0087] (発光ホストと発光ドーパント） [0087] (Light-emitting host and light-emitting dopant)
発光層中の主成分であるホス Η匕合物である発光ホストに対する発光ドーパントとの 混合比は好ましくは質量で 0. 1質量％〜30質量％未満の範囲に調整することであ る。  The mixing ratio of the light-emitting host to the light-emitting host, which is the main component in the light-emitting layer, is preferably adjusted to 0.1% by mass to less than 30% by mass.
[0088] ただし、発光ドーパントは複数種の化合物を混合して用いても良ぐ混合する相手 は構造を異にする、その他の金属錯体やその他の構造を有するリン光性ドーパント や蛍光性ドーパントでもよい。  [0088] However, the light emitting dopant may be a mixture of a plurality of types of compounds, and the mixing partner may have a different structure. Other metal complexes or phosphorescent dopants or fluorescent dopants having other structures may be used. Good.
[0089] ここで、発光ドーパントとして用いられる金属錯体と併用しても良いドーパント（リン 光性ドーパント、蛍光性ドーパント等）について述べる。  Here, dopants (phosphorescent dopants, fluorescent dopants, and the like) that may be used in combination with the metal complex used as the luminescent dopant will be described.
[0090] 発光ドーパントは、大きくわけて、蛍光を発光する蛍光性ドーパントとリン光を発光 するリン光性ドーパントの 2種類がある。  The light-emitting dopant is roughly classified into two types, a fluorescent dopant that emits fluorescence and a phosphorescent dopant that emits phosphorescence.
[0091] 前者（蛍光性ドーパント）の代表例としては、クマリン系色素、ピラン系色素、シァニ ン系色素、クロコニゥム系色素、スクァリウム系色素、ォキソベンツアントラセン系色素 、フルォレセイン系色素、ローダミン系色素、ピリリウム系色素、ペリレン系色素、スチ ルベン系色素、ポリチォフェン系色素、又は希土類錯体系蛍光体等が挙げられる。  [0091] Representative examples of the former (fluorescent dopant) include coumarin-based dyes, pyran-based dyes, cyanine-based dyes, croconium-based dyes, squarium-based dyes, oxobenzanthracene-based dyes, fluorescein-based dyes, and rhodamine-based dyes And pyrylium dyes, perylene dyes, styrven dyes, polythiophene dyes, and rare earth complex fluorescent materials.
[0092] 後者（リン光性ドーパント）の代表例としては、好ましくは元素の周期表で 8属、 9属、 10属の金属を含有する錯体系化合物であり、更に好ましくは、イリジウム化合物、ォ スミゥム化合物であり、中でも最も好ましいのはイリジウム化合物である。  [0092] A typical example of the latter (phosphorescent dopant) is preferably a complex compound containing a metal belonging to Group 8, 9, or 10 of the periodic table of the elements, and more preferably an iridium compound or an iridium compound. Sumidium compounds are the most preferred, and iridium compounds are the most preferred.
[0093] 具体的には以下の特許公報に記載されている化合物である。 [0094] 国際公開第 00/70655号パンフレット、特開 2002— 280178号公報、特開 2001[0093] Specific examples are the compounds described in the following patent publications. [0094] WO 00/70655 pamphlet, JP-A-2002-280178, JP-A-2001-280178
— 181616号公報、特開 2002— 280179号公報、特開 2001— 181617号公報、 特開 2002— 280180号公報、特開 2001— 247859号公報、特開 2002— 299060 号公報、特開 2001— 313178号公報、特開 2002— 302671号公報、特開 2001— 345183号公報、特開 2002— 324679号公報、国際公開第 02/15645号パンフ レット、特開 2002— 332291号公報、特開 2002— 50484号公報、特開 2002— 33 2292号公報、特開 2002— 83684号公報、特表 2002— 540572号公報、特開 20 02— 117978号公報、特開 2002— 338588号公報、特開 2002— 170684号公報 、特開 2002— 352960号公報、国際公開第 01/93642号パンフレット、特開 2002— 181616, JP 2002-280179, JP 2001-181617, JP 2002-280180, JP 2001-247859, JP 2002-299060, JP 2001-313178 JP, JP-A-2002-302671, JP-A-2001-345183, JP-A-2002-324679, International Publication No. WO 02/15645, JP-A-2002-332291, JP-A-2002-50484 JP-A-2002-332292, JP-A-2002-83684, JP-T-2002-540572, JP-A-2002-117978, JP-A-2002-338588, JP-A-2002-170684 JP, JP 2002-352960, WO 01/93642 pamphlet, JP 2002
— 50483号公報、特開 2002— 100476号公報、特開 2002— 173674号公報、特 開 2002— 359082号公報、特開 2002— 175884号公報、特開 2002— 363552号 公報、特開 2002— 184582号公報、特開 2003— 7469号公報、特表 2002— 525 808号公報、特開 2003— 7471号公報、特表 2002— 525833号公報、特開 2003— JP 50483, JP 2002-100476, JP 2002-173674, JP 2002-359082, JP 2002-175884, JP 2002-363552, JP 2002-184582 JP, JP-A-2003-7469, JP-A-2002-525808, JP-A-2003-7471, JP-A-2002-525833, JP-A-2003
— 31366号公報、特開 2002— 226495号公報、特開 2002— 234894号公報、特 開 2002— 235076号公報、特開 2002— 241751号公報、特開 2001— 319779号 公報、特開 2001— 319780号公報、特開 2002— 62824号公報、特開 2002— 10 0474号公報、特開 2002— 203679号公報、特開 2002— 343572号公報、特開 2 002— 203678号公報等。 — JP 31366, JP 2002-226495, JP 2002-234894, JP 2002-235076, JP 2002-241751, JP 2001-319779, JP 2001-319780 JP-A-2002-62824, JP-A-2002-100474, JP-A-2002-203679, JP-A-2002-343572, JP-A-2002-203678 and the like.
[0095] その具体例の一部を下記に示す。  [0095] Some specific examples are shown below.
[0096] [化 19] [0096] [Formula 19]
[0097] [化 20] [0097] [Formula 20]
[0098] [化 21] [0098] [Formula 21]
(発光ホスト） (Light emitting host)
発光ホスト（単にホストともいう）とは、 2種以上の化合物で構成される発光層中にて 混合比（質量）の最も多レ、ィ匕合物のことを意味し、それ以外の化合物にっレ、ては「ド 一パントイ匕合物（単に、ドーパントともいう）」という。例えば、発光層を化合物 A、化合 物 Bという 2種で構成し、その混合比が A: B= 10 : 90であれば化合物 Aがドーパント 化合物であり、化合物 Bがホス H匕合物である。更に、発光層を化合物 A、化合物 B、 化合物 Cの 3種から構成し、その混合比が八：8 :〇= 5 : 10 : 85でぁれば、化合物 A、 化合物 Bがドーパントイ匕合物であり、化合物 Cがホストイ匕合物である。 A light-emitting host (also simply referred to as a host) means a compound having the highest mixing ratio (mass) in a light-emitting layer composed of two or more compounds, and a compound other than that. This is called "do-pant-toy dangling compound (simply called dopant)". For example, if the light-emitting layer is composed of two types, Compound A and Compound B, and the mixture ratio is A: B = 10:90, Compound A is the dopant And compound B is a Hos H conjugate. Further, when the light emitting layer is composed of three kinds of compound A, compound B and compound C, and the mixture ratio is 8: 8: 〇 = 5: 10: 85, compound A and compound B can be combined with the dopant. And compound C is a hostile compound.
[0100] 本発明に用いられる発光ホストとしては、構造的には特に制限はないが、代表的に は力ルバゾール誘導体、トリアリールァミン誘導体、芳香族ボラン誘導体、含窒素複 素環化合物、チォフェン誘導体、フラン誘導体、オリゴァリーレン化合物等の基本骨 格を有するもの、または、カルボリン誘導体やジァザ力ルバゾール誘導体（ここで、ジ ァザカルバゾール誘導体とは、カルボリン誘導体のカルボリン環を構成する炭化水素 環の少なくとも一つの炭素原子が窒素原子で置換されてレ、るものを表す。）等が挙げ られる。 [0100] The light-emitting host used in the present invention is not particularly limited in structure, but is typically a carbazole derivative, a triarylamine derivative, an aromatic borane derivative, a nitrogen-containing complex ring compound, or thiophene. Derivatives, furan derivatives, oligoarylene compounds, and other basic skeletons, or carboline derivatives or diaza carbazole derivatives (here, diazacarbazole derivatives are hydrocarbon rings that constitute the carboline ring of the carboline derivative) In which at least one carbon atom is replaced by a nitrogen atom.
[0101] 中でもカルボリン誘導体、ジァザ力ルバゾール誘導体等が好ましく用いられる。  [0101] Among them, a carboline derivative, a diazaforce rubazole derivative and the like are preferably used.
[0102] 以下に、カルボリン誘導体、ジァザ力ルバゾール誘導体等の具体例を挙げる力 本 発明はこれらに限定されない。これらの化合物は正孔阻止材料として用いられてもよ レ、。 [0102] Hereinafter, specific examples of the carboline derivative, diazaforce rubazole derivative, and the like will be described. The present invention is not limited thereto. These compounds may be used as hole blocking materials.
[0103]  [0103]
[0104] [化 22] [0104] [Formula 22]
また、本発明に用いられる発光ホストは低分子化合物でも、繰り返し単位をもつ高 分子化合物でもよぐビニル基やエポキシ基のような重合性基を有する低分子化合 物 (蒸着重合性発光ホスト)でもレ、レ、。 [0106] 発光ホストとしては、正孔輸送能、電子輸送能を有しつつ、且つ、発光の長波長化 を防ぎ、高 Tg (ガラス転移温度）である化合物が好ましレ、。 The luminescent host used in the present invention may be a low-molecular compound, a high-molecular compound having a repeating unit, or a low-molecular compound having a polymerizable group such as a vinyl group or an epoxy group (evaporation-polymerizable luminescent host). Les, Les ,. As the luminescent host, a compound which has a hole-transporting ability and an electron-transporting ability, prevents a longer wavelength of light emission, and has a high Tg (glass transition temperature) is preferable.
[0107] 発光ホストの具体例としては、以下の文献に記載されている化合物が好適である。  [0107] As specific examples of the light-emitting host, compounds described in the following documents are preferable.
例えば、特開 2001— 257076号公報、同 2002— 308855号公報、同 2001— 313 179号公報、同 2002— 319491号公報、同 2001— 357977号公報、同 2002— 3 34786号公報、同 2002— 8860号公報、同 2002— 334787号公報、同 2002— 1 5871号公報、同 2002— 334788号公報、同 2002— 43056号公報、同 2002— 3 34789号公報、同 2002— 75645号公報、同 2002— 338579号公報、同 2002— 105445号公報、同 2002— 343568号公報、同 2002— 141173号公報、同 2002 — 352957号公報、同 2002— 203683号公報、同 2002— 363227号公報、同 20 For example, JP-A-2001-257076, JP-A-2002-308855, JP-A-2001-313179, JP-A-2002-319949, JP-A-2001-357977, JP-A-2002-334786, and 2002- No. 8860, No. 2002-334787, No. 2002-1 5871, No. 2002-334788, No. 2002-43056, No. 2002-334789, No. 2002-75645, No. 2002 — 338579, 2002-105445, 2002-343568, 2002-141173, 2002 — 352957, 2002-203683, 2002-363227, 20
02— 231453号公報、同 2003— 3165号公報、同 2002— 234888号公報、同 2002-231453, 2003- 3165, 2002-234888, 20
03— 27048号公報、同 2002— 255934号公報、同 2002— 260861号公報、同 2 002— 280183号公報、同 2002— 299060号公報、同 2002— 302516号公報、 同 2002— 305083号公報、同 2002— 305084号公報、同 2002— 308837号公報 等。 No. 03-27048, No. 2002-255934, No. 2002-260861, No. 2002-280183, No. 2002-299060, No. 2002-302516, No. 2002-305083, No. Nos. 2002-305084 and 2002-308837.
[0108] 次に、代表的な有機 EL素子の構成について述べる。  Next, a configuration of a typical organic EL device will be described.
[0109] 《有機 EL素子の構成層》  [0109] << Constituent Layer of Organic EL Element >>
本発明の有機 EL素子の構成層について説明する。  The constituent layers of the organic EL device of the present invention will be described.
[0110] 本発明の有機 EL素子の層構成の好ましい具体例を以下に示す力 本発明はこれ らに限定されない。 （i)陽極/正孔輸送層/発光層/正孔阻止層/電子輸送層/ 陰極 (ii)陽極/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極 (iii)陽極 /正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極 (iv)陽極 /正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極 (V)陽極 /正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファ 一層/陰極 (vi)陽極/陽極バッファ一層/正孔輸送層/電子阻止層/発光層/ 正孔阻止層/電子輸送層/陰極バッファー層/陰極 (vii)陽極/陽極バッファ一層 /正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/陰極バッファ 一層/陰極 《阻止層（電子阻止層、正孔阻止層）》 [0110] The following are preferred specific examples of the layer constitution of the organic EL device of the present invention. The present invention is not limited to these. (I) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode (ii) anode / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / cathode (iii) anode / (Iv) anode / hole transport layer / electron blocking layer / emission layer / hole blocking layer / electron transport layer / cathode (iv) hole transport layer / electron blocking layer / emission layer / hole blocking layer / electron transport layer / cathode ( V) Anode / Hole transport layer / Electron blocking layer / Emitting layer / Hole blocking layer / Electron transport layer / Cathode buffer layer / Cathode (vi) Anode / Anode buffer layer / Hole transport layer / Electron blocking layer / Emitting layer / Hole blocking layer / electron transport layer / cathode buffer layer / cathode (vii) anode / anode buffer layer / hole transport layer / electron blocking layer / emission layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode << Blocking layer (electron blocking layer, hole blocking layer) >>
本発明に係る阻止層（例えば、電子阻止層、正孔阻止層）について説明する。  The blocking layer (for example, an electron blocking layer and a hole blocking layer) according to the present invention will be described.
[0111] 本発明においては、正孔阻止層、電子阻止層等に、本発明の有機 EL素子材料を を用いることが好ましぐ特に好ましくは正孔阻止層に用いることである。 In the present invention, the organic EL device material of the present invention is preferably used for the hole blocking layer, the electron blocking layer, and the like, particularly preferably for the hole blocking layer.
[0112] 本発明の有機 EL素子材料を正孔阻止層、電子阻止層に含有させる場合、請求項 1〜： 17のいずれ力 4項に記載されている、本発明に係る金属錯体を正孔阻止層ゃ電 子阻止層等の層構成成分として 100質量％の状態で含有させてもよいし、他の有機 化合物 (例えば、本発明の有機 EL素子の構成層に用レ、られる化合物等)等と混合し てもよい。 When the organic EL device material of the present invention is contained in a hole blocking layer or an electron blocking layer, the metal complex according to the present invention described in any one of Claims 1 to 17 is used as a hole. The blocking layer may be contained as a layer component of the electron blocking layer or the like in a state of 100% by mass, or may be another organic compound (for example, a compound used for a constituent layer of the organic EL device of the present invention). Etc. may be mixed.
[0113] 本発明に係る阻止層の膜厚としては好ましくは 3nm〜： !OOnmであり、更に好ましく は 5nm〜30nmである。  [0113] The thickness of the blocking layer according to the present invention is preferably from 3 nm to:! OO nm, and more preferably from 5 nm to 30 nm.
[0114] 《正孔阻止層》  [0114] 《Hole blocking layer》
正孔阻止層とは広い意味では電子輸送層の機能を有し、電子を輸送する機能を有 しつつ正孔を輸送する能力が著しく小さい材料からなり、電子を輸送しつつ正孔を阻 止することで電子と正孔の再結合確率を向上させることができる。  The hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a material having a function of transporting electrons and having a very small ability to transport holes, and blocking holes while transporting electrons. By doing so, the recombination probability of electrons and holes can be improved.
[0115] 正孔阻止層としては、例えば特開平 11— 204258号公報、同 11 204359号公 報、及び「有機 EL素子とその工業化最前線（1998年 11月 30日 ェヌ 'ティー'エス 社発行）」の 237頁等に記載の正孔阻止（ホールブロック）層等を本発明に係る正孔 阻止層として適用可能である。また、後述する電子輸送層の構成を必要に応じて、本 発明に係る正孔阻止層として用いることが出来る。  Examples of the hole blocking layer include, for example, JP-A Nos. 11-204258 and 11-204359, and “Organic EL Devices and Their Forefront of Industrialization (N.T. Issue) ”on page 237 and the like can be used as the hole blocking layer according to the present invention. Further, the configuration of the electron transport layer described below can be used as a hole blocking layer according to the present invention, if necessary.
[0116] 《電子阻止層》  [0116] << Electron blocking layer >>
一方、電子阻止層とは広い意味では正孔輸送層の機能を有し、正孔を輸送する機 能を有しつつ電子を輸送する能力が著しく小さい材料からなり、正孔を輸送しつつ電 子を阻止することで電子と正孔の再結合確率を向上させることができる。また、後述 する正孔輸送層の構成を必要に応じて電子阻止層として用いることが出来る。  On the other hand, the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material having a function of transporting holes and having an extremely small ability to transport electrons. By blocking the electrons, the recombination probability of electrons and holes can be improved. Further, the configuration of the hole transport layer described later can be used as an electron blocking layer as needed.
[0117] また、本発明においては、発光層に隣接する隣接層、即ち、正孔阻止層、電子阻 止層に、上記の本発明の有機 EL素子材料を用いることが好ましぐ特に正孔阻止層 に用いることが好ましい。 [0118] 《正孔輸送層》 Further, in the present invention, it is preferable to use the organic EL device material of the present invention for the adjacent layer adjacent to the light emitting layer, that is, for the hole blocking layer and the electron blocking layer, particularly It is preferably used for a blocking layer. [0118] << Hole transport layer >>
正孔輸送層とは正孔を輸送する機能を有する材料を含み、広い意味で正孔注入 層、電子阻止層も正孔輸送層に含まれる。正孔輸送層は単層もしくは複数層設ける こと力 sできる。  The hole transport layer includes a material having a function of transporting holes. In a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer. The hole transport layer can be provided as a single layer or a plurality of layers.
[0119] 正孔輸送材料としては、特に制限はなぐ従来、光導伝材料において、正孔の電荷 注入輸送材料として慣用されているものや EL素子の正孔注入層、正孔輸送層に使 用される公知のものの中力 任意のものを選択して用いることができる。  [0119] The hole transporting material is not particularly limited, and is conventionally used in photoconductive materials as a charge injecting and transporting material for holes and used as a hole injecting layer and a hole transporting layer in EL devices. Any known medium force can be selected and used.
[0120] 正孔輸送材料は、正孔の注入もしくは輸送、電子の障壁性のいずれかを有するも のであり、有機物、無機物のいずれであってもよレ、。例えばトリァゾール誘導体、ォキ サジァゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン 誘導体及びピラゾロン誘導体、フヱニレンジァミン誘導体、ァリールァミン誘導体、アミ ノ置換カルコン誘導体、ォキサゾール誘導体、スチリルアントラセン誘導体、フルォレ ノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、ァニリン系共重 合体、また、導電性高分子オリゴマー、特にチォフェンオリゴマー等が挙げられる。  [0120] The hole transporting material has any of hole injection or transport and electron barrier properties, and may be an organic substance or an inorganic substance. For example, triazole derivatives, oxazidazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives, fluorenone derivatives And hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, especially thiophene oligomers.
[0121] 正孔輸送材料としては、上記のものを使用することができる力 ポルフィリン化合物 、芳香族第三級ァミン化合物及びスチリルァミン化合物、特に芳香族第三級ァミン化 合物を用いることが好ましい。  [0121] As the hole transporting material, the above-mentioned materials can be used. It is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
[0122] 芳香族第三級ァミン化合物及びスチリルァミン化合物の代表例としては、 N, N, N ' , N，一テトラフエニル一 4, 4 '—ジァミノフエニル； N, Ν '—ジフエ二ル一 N, Ν，一ビ ス（3—メチルフエ二ル）一〔1 , 1，一ビフエ二ル〕一 4, 4，一ジァミン（TPD) ; 2, 2—ビ ス（4—ジ一 ρ—トリルァミノフエニル）プロパン； 1 , 1—ビス（4—ジ一 ρ—トリルアミノフ ェニル）シクロへキサン； Ν, Ν, Ν' , Ν，一テトラ一 ρ—トリル一 4， 4 '—ジアミノビフエ ニル； 1， 1—ビス（4—ジ一 ρ—トリルァミノフエニル）一4—フエニルシクロへキサン；ビ ス（4—ジメチルァミノ一 2 -メチルフエニル）フエニルメタン；ビス（4—ジ一 ρ—トリノレア ミノフエニル）フエニルメタン； Ν, Ν，一ジフエニル一 N， N '—ジ（4—メトキシフエニル） -4, 4 '—ジアミノビフエニル； Ν， Ν， Ν' , Ν，一テトラフェニル _4, 4 '—ジアミノジフ ェニルエーテル； 4, 4， _ビス（ジフエニルァミノ）クオードリフエニル； Ν, Ν, Ν—トリ（ρ —トリル）ァミン； 4_ (ジ— ρ—トリルァミノ） _4， - [4 - (ジ— ρ—トリルァミノ）スチリノレ 〕スチルベン； 4— N, N—ジフエニルァミノ一（2—ジフエ二ルビ二ノレ）ベンゼン； 3—メ トキシー 4'—N, N—ジフエニルアミノスチルベンゼン； N—フエ二ルカルバゾール、さ らには、米国特許第 5, 061， 569号明細書に記載されている 2個の縮合芳香族環を 分子内に有するもの、例えば 4， 4' _ビス〔^^_ (1 _ナフチル）_^^_フヱニルァミノ〕 ビフヱニル (NPD)、特開平 4— 308688号公報に記載されているトリフヱニルァミン ユニットが 3つスターバースト型に連結された 4, 4'， 4' ' _トリス〔1^_ (3 _メチルフェ ニル）—N—フヱニルァミノ〕トリフエニルァミン（MTDATA)等が挙げられる。 [0122] Representative examples of the aromatic tertiary amine compound and styrylamine compound include N, N, N ', N, 1-tetraphenyl-1,4,4'-diaminophenyl; N, Ν'-diphenyl-1N, Ν 1,1-bis (3-methylphenyl)-[1,1,1-biphenyl] -1,4,4-diamine (TPD); 2,2-bis (4-di-ρ-tolylaminophenyl) ) Propane; 1,1-bis (4-di-ρ-tolylaminophenyl) cyclohexane; Ν, Ν, Ν ', Ν, tetra-ρ-tolyl-1,4,4'-diaminobiphenyl; 1,1- Bis (4-di-ρ-tolylaminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-ρ-tolinoleaminophenyl) phenylmethane; Ν, Ν, 1-diphenyl-1-N, N'-di (4-methoxyphenyl) -4,4'-diaminobi Enyl; Ν, Ν, Ν ′, Ν, monotetraphenyl _4,4′-diaminodiphenyl ether; 4,4, _bis (diphenylamino) quadriphenyl; Ν, Ν, Ν-tri (ρ-tolyl) amine; 4_ (di-ρ-tolylamino) _4,-[4-(di-ρ-tolylamino) stylinole Stilbene; 4-N, N-diphenylamino-1- (2-diphenylbininole) benzene; 3-methoxy 4'-N, N-diphenylaminostilbenzene; N-phenylcarbazole, and US Pat. No. 5,061,569, which has two fused aromatic rings in the molecule, for example, 4,4′_bis [^^ _ (1_naphthyl) _ ^^ _________________________________________ (3-methylphenyl) -N-phenylamino] triphenylamine (MTDATA).
[0123] さらにこれらの材料を高分子鎖に導入した、またはこれらの材料を高分子の主鎖と した高分子材料を用いることもできる。  [0123] Further, a polymer material in which these materials are introduced into a polymer chain, or in which these materials are used as a polymer main chain, can also be used.
[0124] また、 p型一 Si、 p型一 SiC等の無機化合物も正孔注入材料、正孔輸送材料として 使用すること力 Sできる。また、正孔輸送材料は、高 Tgであることが好ましい。  [0124] In addition, inorganic compounds such as p-type-Si and p-type-SiC can be used as hole injection materials and hole transport materials. Further, the hole transport material preferably has a high Tg.
[0125] この正孔輸送層は、上記正孔輸送材料を、例えば真空蒸着法、スピンコート法、キ ヤスト法、インクジェット法、 LB法等の公知の方法により、薄膜化することにより形成す ること力 Sできる。正孔輸送層の膜厚については特に制限はなレ、が、通常は 5nm〜50 OOnm程度である。この正孔輸送層は、上記材料の一種または二種以上からなる一 層構造であってもよい。  [0125] The hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an inkjet method, and an LB method. That can be S. The thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 500 nm. The hole transport layer may have a single-layer structure composed of one or more of the above materials.
[0126] 《電子輸送層》  [0126] << Electron transport layer >>
電子輸送層とは電子を輸送する機能を有する材料からなり、広い意味で電子注入 層、正孔阻止層も電子輸送層に含まれる。電子輸送層は、単層もしくは複数層を設 けること力 Sできる。  The electron transport layer is made of a material having a function of transporting electrons. In a broad sense, the electron transport layer includes an electron injection layer and a hole blocking layer. The electron transport layer can have a single layer or a plurality of layers.
[0127] 従来、単層の電子輸送層、及び複数層とする場合は発光層に対して陰極側に隣 接する電子輸送層に用レ、られる電子輸送材料 (正孔阻止材料を兼ねる）としては、下 記の材料が知られている。  [0127] Conventionally, when a single electron transport layer and a plurality of layers are used, the electron transport material (also serving as a hole blocking material) used for the electron transport layer adjacent to the light emitting layer on the cathode side is as follows. The following materials are known.
[0128] さらに、電子輸送層は、陰極より注入された電子を発光層に伝達する機能を有して いればよぐその材料としては従来公知の化合物の中力 任意のものを選択して用 レ、ることができる。 [0128] Further, the electron transporting layer is not limited as long as it has a function of transmitting electrons injected from the cathode to the light emitting layer. Let's do it.
[0129] この電子輸送層に用いられる材料 (以下、電子輸送材料という）の例としては、ニト 口置換フルオレン誘導体、ジフヱ二ルキノン誘導体、チォピランジオキシド誘導体、ナ フタレンペリレンなどの複素環テトラカルボン酸無水物、力ノレポジイミド、フレオレニリ デンメタン誘導体、アントラキノジメタン及びアントロン誘導体、ォキサジァゾール誘導 体などが挙げられる。さらに、上記ォキサジァゾール誘導体において、ォキサジァゾ ール環の酸素原子を硫黄原子に置換したチアジアゾール誘導体、電子吸引基として 知られているキノキサリン環を有するキノキサリン誘導体も、電子輸送材料として用い ること力 Sできる。 Examples of the material used for the electron transport layer (hereinafter, referred to as an electron transport material) include a nitro-substituted fluorene derivative, a diphenylquinone derivative, a thiopyran dioxide derivative, and a naphthalene derivative. Examples include heterocyclic tetracarboxylic acid anhydrides such as phthalene perylene, phenolic imide, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, and oxaziazole derivatives. Further, in the above oxadiazole derivative, a thiadiazole derivative in which an oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as the electron transport material.
[0130] さらにこれらの材料を高分子鎖に導入した、またはこれらの材料を高分子の主鎖と した高分子材料を用いることもできる。  [0130] Further, a polymer material in which these materials are introduced into a polymer chain, or in which these materials are used as a polymer main chain, can also be used.
[0131] また、 8 _キノリノール誘導体の金属錯体、例えばトリス（8—キノリノール）アルミユウ ム（Alq)、トリス（5， 7—ジクロロ一 8—キノリノール）アルミニウム、トリス（5, 7—ジブ口 モ _ 8_キノリノール）アルミニウム、トリス（2—メチル _8 _キノリノール）アルミニウム 、トリス（5—メチル _ 8 _キノリノール）アルミニウム、ビス（8—キノリノール）亜鉛（Znq )など、及びこれらの金属錯体の中心金属が In、 Mg、 Cu、 Ca、 Sn、 Ga又は Pbに置 き替わった金属錯体も、電子輸送材料として用いることができる。その他、メタノレフリ 一若しくはメタルフタロシアニン、又はそれらの末端がアルキル基ゃスルホン酸基な どで置換されているものも、電子輸送材料として好ましく用いることができる。また、発 光層の材料として例示したジスチリルビラジン誘導体も、電子輸送材料として用いる ことができるし、正孔注入層、正孔輸送層と同様に、 n型— Si、 n型— SiCなどの無機 半導体も電子輸送材料として用いることができる。  [0131] Further, a metal complex of an 8_quinolinol derivative, for example, tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-18-quinolinol) aluminum, tris (5,7-dibutanol) 8_quinolinol) aluminum, tris (2-methyl_8_quinolinol) aluminum, tris (5-methyl_8_quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc. Metal complexes that replace In, Mg, Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials. In addition, methanol-free or metal phthalocyanine, or those whose terminals are substituted with an alkyl group ゃ sulfonic acid group or the like can be preferably used as the electron transporting material. Also, the distyryl virazine derivative exemplified as the material of the light emitting layer can be used as the electron transporting material, and like the hole injection layer and the hole transport layer, n-type—Si, n-type—SiC, etc. Inorganic semiconductors can also be used as electron transport materials.
[0132] この電子輸送層は、上記電子輸送材料を、例えば真空蒸着法、スピンコート法、キ ヤスト法、インクジェット法、 LB法等の公知の方法により、薄膜化することにより形成す ること力 Sできる。電子輸送層の膜厚については特に制限はないが、通常は 5〜5000 nm程度である。この電子輸送層は、上記材料の一種または二種以上からなる一層 構造であってもよい。  [0132] The electron transport layer is formed by thinning the electron transport material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an ink jet method, and an LB method. S can. The thickness of the electron transport layer is not particularly limited, but is usually about 5 to 5000 nm. The electron transport layer may have a single-layer structure made of one or more of the above materials.
[0133] 次に、本発明の有機 EL素子の構成層として用いられる、注入層について説明する  Next, an injection layer used as a constituent layer of the organic EL device of the present invention will be described.
[0134] 《注入層》：電子注入層、正孔注入層 << Injection layer >>: Electron injection layer, hole injection layer
注入層は必要に応じて設け、電子注入層と正孔注入層があり、上記のごとく陽極と 発光層または正孔輸送層の間、及び、陰極と発光層または電子輸送層との間に存 在させてもよい。 The injection layer is provided as necessary, and has an electron injection layer and a hole injection layer. It may be present between the light emitting layer or the hole transporting layer and between the cathode and the light emitting layer or the electron transporting layer.
[0135] 注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる 層のことで、「有機 EL素子とその工業化最前線（1998年 11月 30日 ェヌ 'ティー'ェ ス社発行）」の第 2編第 2章「電極材料」（123〜166頁）に詳細に記載されており、正 孔注入層（陽極バッファ一層）と電子注入層（陰極バッファ一層）とがある。  [0135] The injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the light emission luminance. "The organic EL element and the forefront of its industrialization (November 30, 1998, N.T. For details, refer to Vol. 2, Chapter 2 “Electrode Materials” (pages 123 to 166) of “Ess Co., Ltd.”. The hole injection layer (one anode buffer layer) and the electron injection layer (one cathode buffer layer) There is.
[0136] 陽極バッファ一層（正孔注入層）は、特開平 9— 45479号公報、同 9一 260062号 公報、同 8— 288069号公報等にもその詳細が記載されており、具体例として、銅フ タロシアニンに代表されるフタロシアニンバッファ一層、酸化バナジウムに代表される 酸化物バッファ一層、アモルファスカーボンバッファ一層、ポリア二リン（ェメラルディ ン)やポリチォフェン等の導電性高分子を用いた高分子バッファ一層等が挙げられる  The anode buffer layer (hole injection layer) is also described in detail in JP-A-9-45479, JP-A-1260062, JP-A-8-288069, and the like. One layer of phthalocyanine buffer represented by copper phthalocyanine, one layer of oxide buffer represented by vanadium oxide, one layer of amorphous carbon buffer, one layer of polymer buffer using conductive polymers such as polyaniline (emeraldine) and polythiophene, etc. Include
[0137] 陰極バッファ一層（電子注入層）は、特開平 6— 325871号公報、同 9 17574号 公報、同 10— 74586号公報等にもその詳細が記載されており、具体的には、スト口 ンチウムゃアルミニウム等に代表される金属バッファ一層、フッ化リチウムに代表され るアルカリ金属化合物バッファ一層、フッ化マグネシウムに代表されるアルカリ土類金 属化合物バッファ一層、酸化アルミニウムに代表される酸化物バッファ一層等が挙げ られる。 [0137] One layer of the cathode buffer (electron injection layer) is described in detail in JP-A-6-325871, JP-A-917574, and JP-A-10-74586. One layer of metal buffer represented by aluminum-aluminum, one layer of alkali metal compound buffer represented by lithium fluoride, one layer of alkaline earth metal compound buffer represented by magnesium fluoride, oxide represented by aluminum oxide One example is a buffer layer.
[0138] 上記バッファ一層（注入層）はごく薄い膜であることが望ましぐ素材にもよる力 そ の膜厚は 0. lnm〜100nmの範囲が好ましい。  It is preferable that the buffer layer (injection layer) is an extremely thin film, and the thickness thereof is preferably in the range of 0.1 nm to 100 nm.
[0139] この注入層は、上記材料を、例えば真空蒸着法、スピンコート法、キャスト法、インク ジェット法、 LB法等の公知の方法により、薄膜ィ匕することにより形成することができる 。注入層の膜厚については特に制限はなレ、が、通常は 5〜5000nm程度である。こ の注入層は、上記材料の一種または二種以上からなる一層構造であってもよい。  [0139] This injection layer can be formed by thin-filming the above-mentioned material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an ink jet method, and an LB method. The thickness of the injection layer is not particularly limited, but is usually about 5 to 5000 nm. The injection layer may have a single-layer structure made of one or more of the above materials.
[0140] 《陽極》  [0140] 《Anode》
本発明の有機 EL素子に係る陽極としては、仕事関数の大きい (4eV以上)金属、 合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用い られる。このような電極物質の具体例としては Au等の金属、 Cul、インジウムチンォキ シド（ITO)、 SnO、 ΖηΟ等の導電性透明材料が挙げられる。また、 IDIXO (In O -As the anode according to the organic EL device of the present invention, a material having a large work function (4 eV or more), a metal, an alloy, an electrically conductive compound and a mixture thereof as an electrode material is preferably used. Specific examples of such electrode materials include metals such as Au, Cul, and indium tin oxide. Examples include conductive transparent materials such as Sido (ITO), SnO, and {η}. Also, IDIXO (In O-
2 2 32 2 3
Zn〇)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極は、これらの 電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィ 一法で所望の形状のパターンを形成してもよぐあるいはパターン精度をあまり必要 としない場合は（100 μ m以上程度）、上記電極物質の蒸着やスパッタリング時に所 望の形状のマスクを介してパターンを形成してもよい。この陽極より発光を取り出す場 合には、透過率を 10%より大きくすることが望ましぐまた、陽極としてのシート抵抗は 数百 Ω /口以下が好ましい。さらに膜厚は材料にもよる力 通常 10nm〜： 1000nm、 好ましくは 10nm〜200nmの範囲で選ばれる。 A material which can produce an amorphous and transparent conductive film such as Zn ( II) may be used. The anode is used to form a thin film by depositing these electrode materials by vapor deposition or sputtering, etc., and to form a pattern of a desired shape by one photolithography method. (about μm or more), and a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode substance. When light emission is extracted from this anode, it is desirable that the transmittance be greater than 10%, and the sheet resistance of the anode is preferably several hundred Ω / port or less. Further, the film thickness is selected depending on the material, usually from 10 nm to: 1000 nm, preferably from 10 nm to 200 nm.
[0141] 《陰極》 [0141] 《Cathode》
一方、本発明に係る陰極としては、仕事関数の小さい (4eV以下）金属（電子注入 性金属と称する）、合金、電気伝導性化合物及びこれらの混合物を電極物質とするも のが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム一力リウ ム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物 、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム /酸化アルミニウム (Al O )混合物、インジウム、リチウム/アルミニウム混合物、希  On the other hand, as the cathode according to the present invention, a metal having a low work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof are used as an electrode material. Specific examples of such electrode materials include sodium, sodium monolithium alloy, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al O) mixture, indium, lithium / aluminum mixture, rare
2 3  twenty three
土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の 点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金 属との混合物、例えばマグネシウム/銀混合物、マグネシウム/アルミニウム混合物 、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム (Al O )混合物  Earth metal and the like. Among these, from the viewpoint of electron injecting property and durability against oxidation, etc., a mixture of an electron injecting metal and a second metal which is a metal having a large work function and a stable value, such as a magnesium / silver mixture, Magnesium / aluminium mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3) mixture
2 3 twenty three
、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極は、これらの電 極物質を蒸着やスパッタリング等の方法により、薄膜を形成させることにより、作製す ること力 sできる。また、陰極としてのシート抵抗は数百 Ω Ζ口以下が好ましぐ膜厚は 通常 10nm〜1000nm、好ましくは 50nm〜200nmの範囲で選ばれる。なお、発光 を透過させるため、有機 EL素子の陽極または陰極のいずれか一方力 S、透明または 半透明であれば発光輝度が向上し好都合である。 , Lithium / aluminum mixtures, aluminum and the like are preferred. The cathode can be manufactured by forming a thin film of these electrode materials by a method such as evaporation or sputtering. The sheet resistance of the cathode is preferably several hundreds of ohms or less, and the preferred film thickness is usually selected in the range of 10 nm to 1000 nm, preferably 50 nm to 200 nm. In order to transmit light, if either the anode S or the cathode S of the organic EL element is transparent or translucent or translucent, the light emission luminance is improved, which is advantageous.
[0142] 《基体 (基板、基材、支持体等ともいう)》 [0142] << Substrate (also referred to as substrate, substrate, support, etc.) >>
本発明の有機 EL素子に係る基体としては、ガラス、プラスチック等の種類には特に 限定はなぐまた、透明のものであれば特に制限はないが、好ましく用いられる基板と しては例えばガラス、石英、光透過性樹脂フィルムを挙げることができる。特に好まし い基体は、有機 EL素子にフレキシブル性を与えることが可能な樹脂フィルムである。 The substrate according to the organic EL device of the present invention is particularly suitable for glass, plastic, and the like. There is no particular limitation as long as the substrate is transparent, but preferably used substrates include, for example, glass, quartz, and a light-transmitting resin film. A particularly preferred substrate is a resin film that can provide flexibility to the organic EL device.
[0143] 樹脂フィルムとしては、例えばポリエチレンテレフタレート（PET)、ポリエチレンナフ タレート（PEN)、ポリエーテルスルホン（PES)、ポリエーテルイミド、ポリエーテルエ ーテルケトン、ポリフエ二レンスルフイド、ポリアリレート、ポリイミド、ポリカーボネート（P C)、セルローストリアセテート（TAC)、セルロースアセテートプロピオネート（CAP) 等からなるフィルム等が挙げられる。  [0143] Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyether sulfone (PES), polyetherimide, polyether ether ketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), Examples of the film include cellulose triacetate (TAC) and cellulose acetate propionate (CAP).
[0144] 樹脂フィルムの表面には、無機物もしくは有機物の被膜またはその両者のハイプリ ッド被膜が形成されていてもよぐ水蒸気透過率が 0. 01g/m2' day' atm以下の高 バリア性フィルムであることが好ましレヽ。 [0144] the surface of the resin film, an inorganic material or coating or High Priestess Tsu Yogu water vapor permeability even de coating is formed 0. 01g / m 2 'day' atm following high barrier for both the organic Preferably it is a film.
[0145] 本発明の有機エレクト口ルミネッセンス素子の発光の室温における外部取り出し効 率は 1%以上であることが好ましぐより好ましくは 2%以上である。ここに、外部取り出 し量子効率（％) =有機 EL素子外部に発光した光子数/有機 EL素子に流した電子 数 X 100である。  [0145] The organic light-emitting device of the present invention has an external extraction efficiency at room temperature of preferably 1% or more, more preferably 2% or more. Here, quantum efficiency taken out (%) = number of photons emitted to the outside of the organic EL element / number of electrons flowing to the organic EL element × 100.
[0146] また、カラーフィルタ一等の色相改良フィルタ一等を併用してもよい。  [0146] A hue improvement filter such as a color filter may be used in combination.
[0147] 照明用途で用いる場合には、発光ムラを低減させるために粗面加工したフィルム（ アンチグレアフイノレム等）を併用することもできる。  [0147] When used for lighting purposes, a film having a roughened surface (such as an anti-glare finolem) may be used in combination to reduce uneven light emission.
[0148] 多色表示装置として用いる場合は少なくとも 2種類の異なる発光極大波長を有する 有機 EL素子からなるが、有機 EL素子を作製する好適な例を説明する。 [0148] When used as a multicolor display device, it is composed of at least two types of organic EL elements having different emission maximum wavelengths. A preferred example of manufacturing an organic EL element will be described.
[0149] 《有機 EL素子の作製方法》 [0149] << Method of Manufacturing Organic EL Element >>
本発明の有機 EL素子の作製方法の一例として、陽極 Z正孔注入層 Z正孔輸送層 As an example of the method for producing the organic EL device of the present invention, an anode Z a hole injection layer Z a hole transport layer
/発光層/正孔阻止層/電子輸送層/陰極バッファー層/陰極からなる有機 EL 素子の作製法について説明する。 A method for fabricating an organic EL device composed of a light-emitting layer, a hole blocking layer, an electron transport layer, a cathode buffer layer, and a cathode will be described.
[0150] まず適当な基体上に、所望の電極物質、例えば陽極用物質からなる薄膜を、 1 μ m 以下、好ましくは 10nm〜200nmの膜厚になるように、蒸着やスパッタリング等の方 法により形成させ、陽極を作製する。次に、この上に素子材料である正孔注入層、正 孔輸送層、発光層、正孔阻止層、電子輸送層等の有機化合物を含有する薄膜を形 成させる。 [0150] First, a thin film made of a desired electrode material, for example, a material for an anode is formed on an appropriate substrate by a method such as evaporation or sputtering so as to have a thickness of 1 µm or less, preferably 10 nm to 200 nm. To form an anode. Next, a thin film containing an organic compound such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer, which are element materials, is formed thereon. Let it run.
[0151] この有機化合物を含有する薄膜の薄膜化の方法としては、前記の如くスピンコート 法、キャスト法、インクジェット法、蒸着法、印刷法等があるが、均質な膜が得られや すぐかつピンホールが生成しにくい等の点から、真空蒸着法またはスピンコート法 が特に好ましい。さらに層ごとに異なる製膜法を適用してもよい。製膜に蒸着法を採 用する場合、その蒸着条件は、使用する化合物の種類等により異なるが、一般にボ ート加熱温度 50°C〜450°C、真空度 10— 6Pa〜10— 2Pa、蒸着速度 0. 01nm〜50nm /秒、基板温度— 50°C〜300°C、膜厚 0. lnm〜5 z mの範囲で適宜選ぶことが望 ましい。 [0151] Examples of the method of thinning the thin film containing the organic compound include a spin coating method, a casting method, an ink jet method, an evaporation method, and a printing method, as described above. The vacuum deposition method or the spin coating method is particularly preferable because a pinhole is not easily generated. Further, a different film forming method may be applied to each layer. If you use the film adopts the deposition, the deposition conditions vary due to kinds of materials used, generally baud preparative heating temperature 50 ° C~450 ° C, vacuum degree of 10- 6 Pa~10- 2 It is desirable to appropriately select a pressure within a range of Pa, a deposition rate of 0.01 nm to 50 nm / sec, a substrate temperature of 50 ° C. to 300 ° C., and a film thickness of 0.1 nm to 5 zm.
[0152] これらの層の形成後、その上に陰極用物質からなる薄膜を、 1 μ m以下好ましくは 5 0nm〜200nmの範囲の膜厚になるように、例えば蒸着やスパッタリング等の方法に より形成させ、陰極を設けることにより、所望の有機 EL素子が得られる。この有機 EL 素子の作製は、一回の真空引きで一貫して正孔注入層から陰極まで作製するのが 好ましいが、途中で取り出して異なる製膜法を施してもかまわない。その際、作業を 乾燥不活性ガス雰囲気下で行う等の配慮が必要となる。  After forming these layers, a thin film made of a cathode material is formed thereon by a method such as evaporation or sputtering so as to have a thickness of 1 μm or less, preferably in the range of 50 nm to 200 nm. A desired organic EL device can be obtained by forming and providing a cathode. In the production of this organic EL device, it is preferable to produce from the hole injection layer to the cathode consistently by one evacuation, but it is also possible to take it out in the middle and apply a different film forming method. At that time, consideration must be given to performing the work in a dry inert gas atmosphere.
[0153] 《表示装置》  [0153] << Display device >>
本発明の表示装置について説明する。  The display device of the present invention will be described.
[0154] 本発明の表示装置は単色でも多色でもよいが、ここでは、多色表示装置について 説明する。多色表示装置の場合は、発光層形成時のみシャドーマスクを設け、一面 に蒸着法、キャスト法、スピンコート法、インクジェット法、印刷法等で膜を形成できる  [0154] The display device of the present invention may be monochromatic or multicolored. Here, a multicolored display device will be described. In the case of a multi-color display device, a shadow mask is provided only when the light-emitting layer is formed, and a film can be formed on one surface by an evaporation method, a casting method, a spin coating method, an inkjet method, a printing method, or the like.
[0155] 発光層のみパターニングを行う場合、その方法に限定はないが、好ましくは蒸着法[0155] When patterning is performed only on the light emitting layer, the method is not particularly limited, but is preferably a vapor deposition method.
、インクジェット法、印刷法である。蒸着法を用いる場合においてはシャドーマスクを 用レ、たパターユングが好ましレ、。 , An inkjet method, and a printing method. When using a vapor deposition method, a shadow mask is used, and Patterjung is preferred.
[0156] また作製順序を逆にして、陰極、電子輸送層、正孔阻止層、発光層、正孔輸送層、 陽極の順に作製することも可能である。 [0156] The production order can be reversed, and the cathode, the electron transport layer, the hole blocking layer, the light emitting layer, the hole transport layer, and the anode can be produced in this order.
[0157] このようにして得られた多色表示装置に、直流電圧を印加する場合には、陽極を +When a DC voltage is applied to the multicolor display device thus obtained, the anode is connected to +
、陰極を—の極性として電圧 2〜40V程度を印加すると、発光が観測できる。また、 逆の極性で電圧を印加しても電流は流れずに発光は全く生じない。さらに、交流電 圧を印加する場合には、陽極が +、陰極が一の状態になったときのみ発光する。な お、印加する交流の波形は任意でよい。 When a voltage of about 2 to 40 V is applied with the negative polarity of the cathode, light emission can be observed. Also, Even if a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Furthermore, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the 1 state. The waveform of the applied AC may be arbitrary.
[0158] 多色表示装置は、表示デバイス、ディスプレー、各種発光光源として用いることがで きる。表示デバイス、ディスプレーにおいて、青、赤、緑発光の 3種の有機 EL素子を 用いることにより、フルカラーの表示が可能となる。  [0158] The multicolor display device can be used as a display device, a display, and various light emission light sources. In display devices and displays, full-color display can be achieved by using three types of organic EL elements that emit blue, red, and green light.
[0159] 表示デバイス、ディスプレーとしてはテレビ、パソコン、モパイル機器、 AV機器、文 字放送表示、自動車内の情報表示等が挙げられる。特に静止画像や動画像を再生 する表示装置として使用してもよぐ動画再生用の表示装置として使用する場合の駆 動方式は単純マトリックス（パッシブマトリックス）方式でもアクティブマトリックス方式で もどちらでもよい。  [0159] Examples of the display device and display include a television, a personal computer, a mopile device, an AV device, a character broadcast display, and information display in a car. In particular, when used as a display device for reproducing moving images, which may be used as a display device for reproducing still images or moving images, the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
[0160] 発光光源としては家庭用照明、車内照明、時計や液晶用のバックライト、看板広告 、信号機、光記憶媒体の光源、電子写真複写機の光源、光通信処理機の光源、光 センサーの光源等が挙げられるがこれに限定するものではない。  [0160] Light-emitting light sources include home lighting, car interior lighting, backlights for watches and LCDs, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copiers, light sources for optical communication processors, and light sensors. A light source or the like may be mentioned, but the light source is not limited thereto.
[0161] 《照明装置》  [0161] 《Lighting device》
本発明の照明装置について説明する。  The lighting device of the present invention will be described.
[0162] 本発明の有機 EL素子に共振器構造を持たせた有機 EL素子として用いてもよぐこ のような共振器構造を有した有機 EL素子の使用目的としては光記憶媒体の光源、 電子写真複写機の光源、光通信処理機の光源、光センサーの光源等が挙げられる 力 これらに限定されなレ、。また、レーザー発振をさせることにより、上記用途に使用 してもよい。  The organic EL device of the present invention may be used as an organic EL device having a resonator structure, and the organic EL device having such a resonator structure may be used as a light source for an optical storage medium, an electronic device, or the like. Light sources for photocopiers, light sources for optical communication processors, light sources for optical sensors, and the like. In addition, laser oscillation may be used for the above purpose.
[0163] また、本発明の有機 EL素子は、照明用や露光光源のような一種のランプとして使 用しても良いし、画像を投影するタイプのプロジェクシヨン装置や、静止画像や動画 像を直接視認するタイプの表示装置 (ディスプレイ）として使用しても良レ、。動画再生 用の表示装置として使用する場合の駆動方式は単純マトリクス (パッシブマトリクス） 方式でもアクティブマトリクス方式でもどちらでも良レ、。または、異なる発光色を有する 本発明の有機 EL素子を 2種以上使用することにより、フルカラー表示装置を作製す ることが可能である。 [0164] 以下、本発明の有機 EL素子を有する表示装置の一例を図面に基づいて説明する [0163] The organic EL device of the present invention may be used as a kind of lamp such as an illumination light source or an exposure light source, a projection device of an image projection type, or a still image or a moving image. It can be used as a display device that can be viewed directly. When used as a display device for video playback, the drive method can be either a simple matrix (passive matrix) method or an active matrix method. Alternatively, a full-color display device can be manufactured by using two or more kinds of the organic EL elements of the present invention having different emission colors. Hereinafter, an example of a display device having the organic EL element of the present invention will be described with reference to the drawings.
[0165] 図 1は、有機 EL素子から構成される表示装置の一例を示した模式図である。有機 EL素子の発光により画像情報の表示を行う、例えば、携帯電話等のディスプレイの 模式図である。 FIG. 1 is a schematic diagram showing an example of a display device including an organic EL element. FIG. 2 is a schematic view of a display such as a mobile phone for displaying image information by light emission of an organic EL element.
[0166] ディスプレイ 1は、複数の画素を有する表示部 A、画像情報に基づいて表示部 Aの 画像走查を行う制御部 B等からなる。  [0166] The display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
[0167] 制御部 Bは、表示部 Aと電気的に接続され、複数の画素それぞれに外部からの画 像情報に基づいて走査信号と画像データ信号を送り、走査信号により走査線毎の画 素が画像データ信号に応じて順次発光して画像走査を行って画像情報を表示部 A に表示する。 [0167] The control unit B is electrically connected to the display unit A, sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside, and controls the pixels for each scanning line by the scanning signal. , Sequentially emit light according to the image data signal, perform image scanning, and display image information on the display unit A.
[0168] 図 2は、表示部 Aの模式図である。 FIG. 2 is a schematic diagram of the display unit A.
[0169] 表示部 Aは基板上に、複数の走査線 5及びデータ線 6を含む配線部と、複数の画 素 3等とを有する。表示部 Aの主要な部材の説明を以下に行う。  The display section A has a wiring section including a plurality of scanning lines 5 and data lines 6 and a plurality of pixels 3 on a substrate. The main members of the display unit A will be described below.
[0170] 図においては、画素 3の発光した光が、白矢印方向（下方向）へ取り出される場合 を示している。  [0170] The figure shows a case where the light emitted from the pixel 3 is extracted in the white arrow direction (downward).
[0171] 配線部の走査線 5及び複数のデータ線 6は、それぞれ導電材料からなり、走査線 5 とデータ線 6は格子状に直交して、直交する位置で画素 3に接続している（詳細は図 示していない）。  [0171] The scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning line 5 and the data line 6 are orthogonal to each other in a grid pattern, and are connected to the pixels 3 at orthogonal positions ( Details are not shown).
[0172] 画素 3は、走査線 5から走査信号が印加されると、データ線 6から画像データ信号を 受け取り、受け取った画像データに応じて発光する。発光の色が赤領域の画素、緑 領域の画素、青領域の画素を、適宜、同一基板上に並置することによって、フルカラ 一表示が可能となる。  When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6, and emits light in accordance with the received image data. By properly arranging pixels in the red, green, and blue light emission regions on the same substrate, full color display is possible.
[0173] 次に、画素の発光プロセスを説明する。  Next, a light emitting process of the pixel will be described.
[0174] 図 3は、画素の模式図である。  FIG. 3 is a schematic diagram of a pixel.
[0175] 画素は、有機 EL素子 10、スイッチングトランジスタ 11、駆動トランジスタ 12、コンデ ンサ 13等を備えている。複数の画素に有機 EL素子 10として、赤色、緑色、青色発 光の有機 EL素子を用レ、、これらを同一基板上に並置することでフルカラー表示を行 うことができる。 The pixel includes an organic EL device 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like. Red, green, and blue light emitting organic EL elements are used as the organic EL elements 10 for a plurality of pixels, and full-color display is performed by juxtaposing these on the same substrate. I can.
[0176] 図 3において、制御部 Bからデータ線 6を介してスイッチングトランジスタ 11のドレイ ンに画像データ信号が印加される。そして、制御部 Bから走査線 5を介してスィッチン グトランジスタ 11のゲートに走查信号が印加されると、スイッチングトランジスタ 11の 駆動がオンし、ドレインに印加された画像データ信号がコンデンサ 13と駆動トランジ スタ 12のゲートに伝達される。  In FIG. 3, an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6. Then, when a scan signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5, the drive of the switching transistor 11 is turned on, and the image data signal applied to the drain is driven by the capacitor 13 It is transmitted to the gate of transistor 12.
[0177] 画像データ信号の伝達により、コンデンサ 13が画像データ信号の電位に応じて充 電されるとともに、駆動トランジスタ 12の駆動がオンする。駆動トランジスタ 12は、ドレ インが電源ライン 7に接続され、ソースが有機 EL素子 10の電極に接続されており、ゲ 一トに印加された画像データ信号の電位に応じて電源ライン 7から有機 EL素子 10に 電流が供給される。  By transmitting the image data signal, the capacitor 13 is charged according to the potential of the image data signal, and the driving of the driving transistor 12 is turned on. The drive transistor 12 has a drain connected to the power supply line 7, a source connected to the electrode of the organic EL element 10, and an organic EL element connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Element 10 is supplied with current.
[0178] 制御部 Bの順次走查により走查信号が次の走査線 5に移ると、スイッチングトランジ スタ 11の駆動がオフする。しかし、スイッチングトランジスタ 11の駆動がオフしてもコン デンサ 13は充電された画像データ信号の電位を保持するので、駆動トランジスタ 12 の駆動はオン状態が保たれて、次の走査信号の印加が行われるまで有機 EL素子 1 0の発光が継続する。順次走査により次に走査信号が印加されたとき、走査信号に 同期した次の画像データ信号の電位に応じて駆動トランジスタ 12が駆動して有機 E L素子 10が発光する。  [0178] When the scan signal moves to the next scanning line 5 due to the sequential running of the control unit B, the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied. The organic EL element 10 continues to emit light until the light is emitted. When the next scanning signal is applied by the sequential scanning, the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
[0179] すなわち、有機 EL素子 10の発光は、複数の画素それぞれの有機 EL素子 10に対 して、アクティブ素子であるスイッチングトランジスタ 11と駆動トランジスタ 12を設けて 、複数の画素 3それぞれの有機 EL素子 10の発光を行っている。このような発光方法 をアクティブマトリクス方式と呼んでレ、る。  In other words, the organic EL element 10 emits light by providing a switching transistor 11 and a driving transistor 12 as active elements for the organic EL elements 10 of each of the plurality of pixels, and The element 10 emits light. Such a light emitting method is called an active matrix method.
[0180] ここで、有機 EL素子 10の発光は、複数の階調電位を持つ多値の画像データ信号 による複数の階調の発光でもよいし、 2値の画像データ信号による所定の発光量の オン、オフでもよい。  Here, the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-valued image data signal having a plurality of gradation potentials, or light emission of a predetermined light emission amount by a binary image data signal. It may be on or off.
[0181] また、コンデンサ 13の電位の保持は、次の走查信号の印加まで継続して保持して もよレ、し、次の走查信号が印加される直前に放電させてもょレ、。  [0181] The potential of the capacitor 13 may be maintained until the next scan signal is applied, or may be discharged immediately before the next scan signal is applied. ,.
[0182] 本発明においては、上述したアクティブマトリクス方式に限らず、走查信号が走查さ れたときのみデータ信号に応じて有機 EL素子を発光させるパッシブマトリクス方式の 発光駆動でもよい。 [0182] In the present invention, the running signal is not limited to the above-described active matrix system. A passive matrix light emission drive in which the organic EL element emits light in accordance with the data signal only when the light is emitted may be used.
[0183] 図 4は、パッシブマトリクス方式による表示装置の模式図である。図 4におレ、て、複 数の走査線 5と複数の画像データ線 6が画素 3を挟んで対向して格子状に設けられ ている。  FIG. 4 is a schematic diagram of a display device using a passive matrix method. In FIG. 4, a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
[0184] 順次走查により走査線 5の走查信号が印加されたとき、印加された走査線 5に接続 している画素 3が画像データ信号に応じて発光する。パッシブマトリクス方式では画 素 3にアクティブ素子が無ぐ製造コストの低減が計れる。  [0184] When the scan signal of the scan line 5 is applied by the sequential scan, the pixels 3 connected to the applied scan line 5 emit light according to the image data signal. In the passive matrix method, since there is no active element in pixel 3, the manufacturing cost can be reduced.
[0185] 本発明に係わる有機 EL材料は、また、照明装置として、実質白色の発光を生じる 有機 EL素子に適用できる。複数の発光材料により複数の発光色を同時に発光させ て混色により白色発光を得る。複数の発光色の組み合わせとしては、青色、緑色、青 色の 3原色の 3つの発光極大波長を含有させたものでも良いし、青色と黄色、青緑と 橙色等の補色の関係を利用した 2つの発光極大波長を含有したものでも良い。  [0185] The organic EL material according to the present invention can also be applied to an organic EL element that emits substantially white light as a lighting device. A plurality of light emitting colors are emitted simultaneously by a plurality of light emitting materials, and white light is obtained by mixing colors. As a combination of a plurality of emission colors, a combination of three emission maximum wavelengths of the three primary colors of blue, green and blue may be used, or a combination of complementary colors such as blue and yellow, and blue-green and orange may be used. It may be one containing two emission maximum wavelengths.
[0186] また、複数の発光色を得るための発光材料の組み合わせは、複数のリン光または 蛍光を発光する材料 (発光ドーパント）を、複数組み合わせたもの、蛍光またはリン光 を発光する発光材料と、該発光材料力 の光を励起光として発光する色素材料とを 組み合わせたもののレ、ずれでも良レ、が、本発明に係わる白色有機エレクト口ルミネッ センス素子においては、発光ドーパントを複数組み合わせる方式が好ましい。  [0186] In addition, the combination of light-emitting materials for obtaining a plurality of emission colors includes a combination of a plurality of phosphorescent or fluorescent light-emitting materials (light-emitting dopants) and a fluorescent or phosphorescent light-emitting material. Although a combination of a dye material that emits light with the light of the light emitting material as excitation light and a good displacement can be achieved, the white organic electorophore luminescent device according to the present invention employs a method of combining a plurality of luminescent dopants. preferable.
[0187] 複数の発光色を得るための有機エレクト口ルミネッセンス素子の層構成としては、複 数の発光ドーパントを、一つの発光層中に複数存在させる方法、複数の発光層を有 し、各発光層中に発光波長の異なるドーパントをそれぞれ存在させる方法、異なる波 長に発光する微小画素をマトリックス状に形成する方法等が挙げられる。  [0187] The layer structure of the organic electroluminescent device for obtaining a plurality of luminescent colors includes a method in which a plurality of luminescent dopants are present in a single luminescent layer, and a method in which a plurality of luminescent layers are provided. Examples include a method in which dopants having different emission wavelengths are present in the layer, and a method in which minute pixels that emit light with different wavelengths are formed in a matrix.
[0188] 本発明に係わる白色有機エレクト口ルミネッセンス素子においては、必要に応じ製 膜時にメタルマスクやインクジェットプリンティング法等でパターユングを施してもよい [0188] In the white organic electroluminescent device according to the present invention, a patterning may be performed by a metal mask, an inkjet printing method, or the like at the time of film formation, if necessary.
。パターユングする場合は、電極のみをパターユングしてもいいし、電極と発光層を パターユングしてもレ、レ、し、素子全層をパターユングしてもレ、レ、。 . When patterning is performed, only the electrode may be patterned, or the electrode and the light emitting layer may be patterned or checked, and the entire element layer may be patterned or checked.
[0189] 発光層に用いる発光材料としては特に制限はなぐ例えば液晶表示素子における バックライトであれば、 CF (カラーフィルター）特性に対応した波長範囲に適合するよ うに、本発明に係わる白金錯体、また公知の発光材料の中から任意のものを選択し て組み合わせて白色化すれば良い。 [0189] The light emitting material used for the light emitting layer is not particularly limited. For example, in the case of a backlight of a liquid crystal display element, the light emitting material is suitable for a wavelength range corresponding to CF (color filter) characteristics. As described above, the platinum complex according to the present invention or any of known luminescent materials may be selected and combined to whiten.
[0190] このように、本発明の白色発光有機 EL素子は、前記表示デバイス、ディスプレーに カロえて、各種発光光源、照明装置として、家庭用照明、車内照明、また、露光光源の ような一種のランプとして、液晶表示装置のバックライト等、表示装置にも有用に用い られる。  [0190] As described above, the white light-emitting organic EL element of the present invention can be used as a kind of light source and lighting device such as home lighting, in-car lighting, and exposure light as a light source for the display device and display. As a lamp, it is usefully used for a display device such as a backlight of a liquid crystal display device.
[0191] その他、時計等のバックライト、看板広告、信号機、光記憶媒体等の光源、電子写 真複写機の光源、光通信処理機の光源、光センサーの光源等、更には表示装置を 必要とする一般の家庭用電気器具等広い範囲の用途が挙げられる。  [0191] In addition, a backlight such as a clock, a signboard advertisement, a traffic light, a light source such as an optical storage medium, a light source of an electronic photocopier, a light source of an optical communication processor, a light source of an optical sensor, and a display device are required. And a wide range of applications such as general household electric appliances.
実施例  Example
[0192] 以下、実施例により本発明を説明するが、本発明はこれらに限定されない。また、 実施例に用レ、る化合物を下記に示す。  Hereinafter, the present invention will be described with reference to Examples, but the present invention is not limited thereto. The compounds used in the examples are shown below.
[0193] [化 23] [0193] [Formula 23]
[0194] [化 24] [0194] [Formula 24]
α -NPD CBP α-NPD CBP
[0195] 実施例 1 [0195] Example 1
《有機 EL素子 OLEDl _ 1の作製》  << Preparation of organic EL element OLEDl_1 >>
陽極としてガラス上に ITOを 150nm成膜した基板 (NHテクノグラス社製: NA— 45 )にパターユングを行った後、この ITO透明電極を設けた透明支持基板を iso プロ ピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、 UVオゾン洗浄を 5分間行 つた。この透明支持基板を、市販の真空蒸着装置の基板ホルダーに固定し、一方、 5つのタンタル製抵抗加熱ボートに、 ひ _NPD、 CBP、 Ir_ 12、 BCP、 Alqをそれ ぞれ入れ、真空蒸着装置 (第 1真空槽）に取付けた。  After patterning a 150 nm ITO substrate on glass (manufactured by NH Technoglass Co., Ltd .: NA-45) as an anode, the transparent support substrate provided with the ITO transparent electrodes was ultrasonically cleaned with isopropyl alcohol. Then, drying with dry nitrogen gas was performed, and UV ozone cleaning was performed for 5 minutes. This transparent support substrate is fixed to the substrate holder of a commercially available vacuum evaporation system, while _NPD, CBP, Ir_12, BCP, and Alq are placed in five tantalum resistance heating boats, respectively, and the vacuum evaporation system ( (First vacuum chamber).
[0196] 更に、タンタル製抵抗加熱ボートにフッ化リチウムを、タングステン製抵抗加熱ボー トにアルミニウムをそれぞれ入れ、真空蒸着装置の第 2真空槽に取り付けた。  [0196] Further, lithium fluoride was placed in a tantalum resistance heating boat, and aluminum was placed in a tungsten resistance heating boat, and they were attached to a second vacuum chamber of a vacuum evaporation apparatus.
[0197] まず、第 1の真空槽を 4 X 10— 4Paまで減圧した後、 α NPDの入った前記加熱ボ ートに通電して加熱し、蒸着速度 0. lnm/秒〜 0. 2nm/秒で透明支持基板に膜 厚 25nmの厚さになるように蒸着し、正孔注入/輸送層を設けた。 [0197] First, after the vacuum of the first vacuum chamber to 4 X 10- 4 Pa, and heated by supplying an electric current to the baud preparative containing the alpha NPD, deposition rate 0. lnm / sec ~ 0. 2 nm Vapor deposition was performed on a transparent support substrate at a thickness of 25 nm / sec to provide a hole injection / transport layer.
[0198] さらに、 CBPの入った前記加熱ボートと Ir 12の入ったボートをそれぞれ独立に通 電して発光ホストである CBPと発光ドーパントである Ir— 12の蒸着速度が 100 : 7にな るように調節し膜厚 30nmの厚さになるように蒸着し、発光層を設けた。  [0198] Further, the heating boat containing CBP and the boat containing Ir12 are independently passed through, and the deposition rate of CBP as a light emitting host and Ir-12 as a light emitting dopant becomes 100: 7. This was adjusted to a thickness of 30 nm to provide a light emitting layer.
[0199] ついで、 BCPの入った前記加熱ボートに通電して加熱し、蒸着速度 0. lm/秒〜 0. 2nm/秒で厚さ lOnmの正孔阻止層を設けた。さらに、 Alqの入った前記加熱ボ [0199] Next, the heating boat containing the BCP was energized and heated, and the deposition rate was set to 0.1 lm / sec. A hole blocking layer having a thickness of lOnm at 0.2 nm / sec was provided. In addition, the heating chamber containing Alq
3  Three
ートを通電して加熱し、蒸着速度 0. lnm/秒〜 0. 2nm/秒で膜厚 40nmの電子 輸送層を設けた。  The sheet was heated by energization, and an electron transport layer having a thickness of 40 nm was provided at a deposition rate of 0.1 nm / sec to 0.2 nm / sec.
[0200] 次に、前記の如く電子輸送層まで製膜した素子を真空のまま第 2真空槽に移した 後、電子輸送層の上にステンレス鋼製の長方形穴あきマスクが配置されるように装置 外部からリモートコントロールして設置した。  [0200] Next, after the element formed up to the electron transport layer as described above was transferred to a second vacuum chamber while maintaining a vacuum, a rectangular perforated mask made of stainless steel was arranged on the electron transport layer. Equipment Installed by remote control from outside.
[0201] 第 2真空槽を 2 X 10— 4Paまで減圧した後、フッ化リチウム入りのボートに通電して蒸 着速度 0. OlnmZ秒〜 0. 02nmZ秒で膜厚 0. 5nmの陰極バッファ一層を設け、 次いでアルミニウムの入ったボートに通電して蒸着速度 lnm/秒〜 2nmZ秒で膜厚 150nmの陰極をつけた。さらにこの有機 EL素子を大気に接触させることなく窒素雰 囲気下のグローブボックス（純度 99. 999%以上の高純度窒素ガスで置換したグロ ーブボックス）へ移し、図 5に示したような内部を窒素で置換した封止構造にして、有 機 EL素子 OLED1— 1を作製した。 [0201] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, a cathode buffer steam Chakusokudo 0. OlnmZ sec ~ 0. 02nmZ seconds at a film thickness of 0. 5 nm by supplying an electric current to the boat lithium fluoride-containing One layer was provided, and then a boat containing aluminum was energized to apply a 150 nm-thick cathode at a deposition rate of 1 nm / sec to 2 nmZ seconds. Furthermore, the organic EL element was transferred to a glove box (a glove box replaced with a high-purity nitrogen gas having a purity of 99.999% or more) in a nitrogen atmosphere without being brought into contact with the atmosphere. The organic EL element OLED1-1 was fabricated with the sealing structure replaced by.
[0202] なお、捕水剤である酸化バリウム 105は、アルドリッチ社製の高純度酸化バリウム粉 末を、粘着剤付きのフッ素樹脂系半透過膜 (ミクロテックス S— NTF8031Q 日東 電工製)でガラス製封止缶 104に貼り付けたものを予め準備して使用した。封止缶と 有機 EL素子の接着には紫外線硬化型接着剤 107を用い、紫外線ランプを照射する ことで両者を接着し封止素子を作製した。  [0202] Barium oxide 105, a water-trapping agent, is made of a high-purity barium oxide powder manufactured by Aldrich Co., Ltd. using a fluororesin semi-permeable membrane with adhesive (Microtex S-NTF8031Q manufactured by Nitto Denko). What was pasted on the sealing can 104 was prepared and used in advance. The sealing can was bonded to the organic EL element by using an ultraviolet-curing adhesive 107 and irradiating an ultraviolet lamp to bond the two together to produce a sealing element.
[0203] 図 5において 101は透明電極を設けたガラス基板、 102が前記正孔注入/輸送層 、発光層、正孔阻止層、電子輸送層等からなる有機 EL層、 103は陰極を示す。  In FIG. 5, 101 is a glass substrate provided with a transparent electrode, 102 is an organic EL layer including the above-described hole injection / transport layer, light emitting layer, hole blocking layer, electron transport layer, and 103 is a cathode.
[0204] 《有機 EL素子 OLED1— 2〜：!一 24の作製》  [0204] << Preparation of organic EL element OLED1-2 ~:! Ichi 24 >>
上記の有機 EL素子 OLED1— 1の作製において、表 1に記載のように、発光ホスト 、発光ドーパント及び正孔阻止材料を、各々変更した以外は同様にして、有機 EL素 子 OLED 1— 2〜： 1— 24を作製した。  In the preparation of the above-mentioned organic EL element OLED1-1, as shown in Table 1, the organic EL elements OLED1-2 to OLED1-2 to luminescent host, luminescent dopant and hole blocking material were changed in the same manner, respectively. : 1-24 were prepared.
[0205] 得られた有機 EL素子〇LED1 _ :！〜 1— 24について下記のような評価を行った。  [0205] The obtained organic EL device @ LED1 _:! 1 to 24 were evaluated as follows.
[0206] 《外部取り出し量子効率》  [0206] 《External extraction quantum efficiency》
有機 EL素子 OLED1— 1〜： 1— 24を室温（約 23°C〜25°C)、 2. 5mA/cm2の定 電流条件下による点灯を行い、点灯開始直後の発光輝度 (U [cd/m2]を測定する ことにより、外部取り出し量子効率（77 )を算出した。ここで、発光輝度の測定は、 CS 1000 (ミノルタ製）を用いた。 The organic EL element OLED1-1 to 1-24 is lit at room temperature (about 23 ° C to 25 ° C) at a constant current of 2.5 mA / cm 2 , and the light emission luminance (U [cd / m 2 ] Thereby, the external extraction quantum efficiency (77) was calculated. Here, the measurement of the light emission luminance used CS1000 (made by Minolta).
[0207] また、外部取り出し量子効率は、有機 EL素子 OLED1— 1を 100とした時の相対値 で表した。  [0207] The external extraction quantum efficiency was expressed as a relative value when the organic EL element OLED1-1 was set to 100.
[0208] 《発光寿命》  [0208] 《Emission life》
有機 EL素子 OLED1— :！〜 1— 24を室温下、 2. 5mA/cm2の定電流条件下によ る連続点灯を行い、初期輝度の半分の輝度になるのに要する時間（ τ / )を測定し Organic EL element OLED1—:! 1 to 24 were continuously lit at room temperature under a constant current of 2.5 mA / cm2, and the time required to reach half the initial luminance (τ /) was measured.
1 2 た。また、発光寿命は、有機 EL素子 OLED1— 1を 100と設定した時の相対値で表 した。  1 2 The light emission lifetime was expressed as a relative value when the organic EL element OLED1-1 was set to 100.
[0209] 得られた結果を表 1に示す。  [0209] The obtained results are shown in Table 1.
[0210] [表 1] [0210] [Table 1]
[0211] 表 1から、本発明に係る金属錯体を用いて作製した有機 EL素子は比較有機 EL素 子に比べ、高い発光効率と、発光寿命の長寿命化が達成できることが明らかである。  [0211] From Table 1, it is clear that the organic EL device manufactured using the metal complex according to the present invention can achieve higher luminous efficiency and longer luminescent life than the comparative organic EL device.
[0212] 更に、カルボリン誘導体または該カルボリン誘導体のカルボリン環を構成する炭化 水素環の炭素原子の少なくとも一つが更に窒素原子で置換されている環構造を有 する誘導体を発光層に併用することにより、また、カルボリン誘導体または該カルボリ ン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが更に 窒素原子で置換されている環構造を有する誘導体を正孔阻止層に使用することによ り、更に本発明に記載の効果の向上が見られた。 [0212] Further, a carboline derivative or a carbon atom constituting the carboline ring of the carboline derivative When a derivative having a ring structure in which at least one of carbon atoms of a hydrogen ring is further substituted with a nitrogen atom is used in combination with the light emitting layer, a carboline derivative or a hydrocarbon ring constituting the carboline ring of the carbine derivative is used. By using a derivative having a ring structure in which at least one of the carbon atoms is further substituted with a nitrogen atom for the hole blocking layer, the effect described in the present invention was further improved.
[0213] 実施例 2 [0213] Example 2
《有機 EL素子〇LED2 _ 1の作製》  《Production of organic EL device 〇 LED2_1》
陽極としてガラス上に ITOを 150nm成膜した基板 (NHテクノグラス社製: NA— 45 )にパターユングを行った後、この ITO透明電極を設けた透明支持基板を iso プロ ピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、 UVオゾン洗浄を 5分間行 つた。  After patterning a 150 nm ITO substrate on glass (manufactured by NH Technoglass Co., Ltd .: NA-45) as an anode, the transparent support substrate provided with the ITO transparent electrodes was ultrasonically cleaned with isopropyl alcohol. Then, drying with dry nitrogen gas was performed, and UV ozone cleaning was performed for 5 minutes.
[0214] この透明支持基板を、市販の真空蒸着装置の基板ホルダーに固定し、一方、 5つ のタンタル製抵抗加熱ボートに、 a—NPD、 CBP、 Ir—12、 BCP、 Alqをそれぞれ 入れ、真空蒸着装置 (第 1真空槽）に取付けた。  [0214] The transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while a-NPD, CBP, Ir-12, BCP, and Alq were placed in five tantalum resistance heating boats, respectively. It was attached to a vacuum evaporation system (first vacuum tank).
[0215] さらに、タンタル製抵抗加熱ボートにフッ化リチウムを、タングステン製抵抗加熱ボ ートにアルミニウムをそれぞれ入れ、真空蒸着装置の第 2真空槽に取り付けた。 [0215] Further, lithium fluoride was placed in a resistance heating boat made of tantalum and aluminum was placed in a resistance heating boat made of tungsten, and they were attached to a second vacuum tank of a vacuum evaporation apparatus.
[0216] まず、第 1の真空槽を 4 X 10— 4Paまで減圧した後、 α NPDの入った前記加熱ボ ートに通電して加熱し、蒸着速度 0. lnm/秒〜 0. 2nm/秒で透明支持基板に膜 厚 30nmの厚さになるように蒸着し、正孔注入/輸送層を設けた。 [0216] First, after the vacuum of the first vacuum chamber to 4 X 10- 4 Pa, and heated by supplying an electric current to the baud preparative containing the alpha NPD, deposition rate 0. lnm / sec ~ 0. 2 nm Vapor deposition was performed on the transparent support substrate at a rate of 30 nm / sec to provide a hole injection / transport layer.
[0217] さらに、 CBPの入った前記加熱ボートと Ir 12の入ったボートをそれぞれ独立に通 電して発光ホストである CBPと発光ドーパントである Ir— 12の蒸着速度が 100 : 7にな るように調節し膜厚 30nmの厚さになるように蒸着し、発光層を設けた。 [0217] Further, the heating boat containing CBP and the boat containing Ir12 are independently passed through, and the deposition rate of CBP as a light emitting host and Ir-12 as a light emitting dopant becomes 100: 7. This was adjusted to a thickness of 30 nm to provide a light emitting layer.
[0218] ついで、 BCPの入った前記加熱ボートに通電して加熱し、蒸着速度 0. InmZ秒[0218] Next, the heating boat containing the BCP was energized and heated, and the evaporation rate was set to 0. InmZ seconds.
〜0. 2nmZ秒で厚さ 10nmの正孔阻止層を設けた。さらに、 Alqの入った前記加熱 ボートを通電して加熱し、蒸着速度 0. lnm/秒〜 0. 2nmZ秒で膜厚 30nmの電子 輸送層を設けた。 A hole blocking layer having a thickness of 10 nm and a thickness of 0.2 nmZ seconds was provided. Further, the heating boat containing Alq was energized and heated to provide an electron transport layer having a thickness of 30 nm at a deposition rate of 0.1 nm / sec to 0.2 nmZ second.
[0219] 次に、前記の如く電子輸送層まで製膜した素子を真空のまま第 2真空槽に移した 後、電子輸送層の上にステンレス鋼製の長方形穴あきマスクが配置されるように装置 外部からリモートコントロールして設置した。 [0219] Next, after the device formed as described above up to the electron transport layer was transferred to the second vacuum chamber while maintaining a vacuum, a rectangular perforated mask made of stainless steel was placed on the electron transport layer. apparatus Installed by remote control from outside.
[0220] 第 2真空槽を 2 X 10— 4Paまで減圧した後、フッ化リチウム入りのボートに通電して蒸 着速度 0. Olnm/秒〜 0. 02nm/秒で膜厚 0. 5nmの陰極バッファ一層を設け、 次いでアルミニウムの入ったボートに通電して蒸着速度 l〜2nm/秒で膜厚 150nm の陰極をつけた。さらにこの有機 EL素子を大気に接触させることなく窒素雰囲気下 のグローブボックス（純度 99. 999%以上の高純度窒素ガスで置換したグローブボッ タス）へ移し、図 5に示したような内部を窒素で置換した封止構造にして、有機 EL素 子 OLED1— 1を作製した。なお、捕水剤である酸化バリウム 105は、ァノレドリツチ社 製の高純度酸化バリウム粉末を、粘着剤付きのフッ素樹脂系半透過膜 (ミクロテックス[0220] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, at a steam Chakusokudo 0. Olnm / sec ~ 0. 02nm / sec thickness 0. 5 nm of energizing the boat lithium fluoride-containing A cathode buffer layer was provided, and then a boat containing aluminum was energized to provide a cathode having a thickness of 150 nm at a deposition rate of 1 to 2 nm / sec. Furthermore, the organic EL device was transferred to a glove box under a nitrogen atmosphere (a glove box replaced with high-purity nitrogen gas having a purity of 99.999% or more) without being brought into contact with the atmosphere. Then, an organic EL device OLED1-1 was produced with the sealing structure replaced with. In addition, barium oxide 105, which is a water trapping agent, is obtained by coating a high-purity barium oxide powder manufactured by Anoredrich Co. with a fluororesin semi-permeable membrane with an adhesive (Microtex
S -NTF8031Q 日東電工製）でガラス製封止缶 104に貼り付けたものを予め準 備して使用した。封止缶と有機 EL素子の接着には紫外線硬化型接着剤 107を用い 、紫外線ランプを照射することで両者を接着し封止素子を作製した。図 5において 10 1は透明電極を設けたガラス基板、 102が前記正孔注入/輸送層、発光層、正孔阻 止層、電子輸送層等からなる有機 EL層、 103は陰極を示す。 S-NTF8031Q (manufactured by Nitto Denko), which was attached to a glass sealing can 104, was used in advance as a preparation. The sealing can was bonded to the organic EL element by using an ultraviolet-curing adhesive 107 and irradiating an ultraviolet lamp to bond the two together to produce a sealing element. In FIG. 5, 101 is a glass substrate provided with a transparent electrode, 102 is an organic EL layer composed of the hole injection / transport layer, light emitting layer, hole blocking layer, electron transport layer, etc., and 103 is a cathode.
[0221] 《有機 EL素子 OLED2— 2〜2— 19の作製》  [0221] << Preparation of organic EL element OLED2-2-2-2-19 >>
上記の有機 EL素子 OLED2— 1の作製において、表 1に記載のように、発光ホスト 、発光ドーパント及び正孔阻止材料を、各々変更した以外は同様にして、有機 EL素 子 OLED2— 2〜 2— 19を作製した。  In the production of the above-mentioned organic EL element OLED2-1, as shown in Table 1, the organic EL elements OLED2-2 to 2-2 were prepared in the same manner except that the light-emitting host, the light-emitting dopant and the hole-blocking material were respectively changed. — 19 was made.
[0222] 得られた有機 EL素子 OLED2— :!〜 2— 19について、外部取り出し量子効率につ レ、て実施例 1と同様の方法で評価を行つた。  [0222] The obtained organic EL devices OLED2-:! To 2-19 were evaluated in the same manner as in Example 1 for the quantum efficiency extracted from the outside.
[0223] 《発光寿命》  [0223] << Emission life >>
有機 EL素子 OLED2—：!〜 2— 19を室温下、 2. 5mA/cm2の定電流条件下によ る連続点灯を行い、初期輝度の 90%の輝度になるのに要する時間（ τ / )を測定し Organic EL element OLED2—:! To 2—19 are continuously lit at room temperature under a constant current of 2.5 mA / cm 2 , and the time required to reach 90% of the initial luminance (τ / )
1 9 た。尚、外部取り出し量子効率は、有機 EL素子 OLED2— 1を 100とした時の相対 値、発光寿命は、有機 EL素子 OLED2— 1を 100とした時の相対値で表した。  1 9 The external extraction quantum efficiency was represented by a relative value when the organic EL element OLED2-1 was set to 100, and the light emission life was represented by a relative value when the organic EL element OLED2-1 was set to 100.
[0224] 得られた結果を表 2に示す。  [0224] The obtained results are shown in Table 2.
[0225] [表 2] 外部取り出し 発光寿命 素子 No. 発光ホス ト 発光ド一パント 正孔阻止材料 備 考 量子効率 ( τ 1 9) [0225] [Table 2] Outgoing emission lifetime Element No. Emission host Emission dopant Hole blocking material Remarks Quantum efficiency (τ 19)
0LED2-1 CBP lr—12 BCP 100 100 比 較 0LED2-1 CBP lr-12 BCP 100 100 Compare
0LED2-2 CBP lr-13 BCP 104 106 比 較0 LED2-2 CBP lr-13 BCP 104 106 Comparison
0LED2-3 CBP 比較 1 BCP 100 95 比 較0 LED2-3 CBP comparison 1 BCP 100 95 comparison
0LED2-4 CBP 2-1 BCP 122 185 本発明0LED2-4 CBP 2-1 BCP 122 185 The present invention
0LED2-5 CBP 2-3 BCP 129 198 本発明0LED2-5 CBP 2-3 BCP 129 198 The present invention
0LED2-6 CBP 2-4 BCP 122 177 本発明0LED2-6 CBP 2-4 BCP 122 177 Present invention
0LED2-7 CBP 2-5 BCP 124 170 本発明0LED2-7 CBP 2-5 BCP 124 170 The present invention
0LED2-8 CBP 2-7 BCP 123 183 本発明0LED2-8 CBP 2-7 BCP 123 183 The present invention
0LED2-9 CBP 2—10 BCP 117 171 本発明0LED2-9 CBP 2-10 BCP 117 171 Present invention
0LED2-10 CBP 2-11 BCP 128 188 本発明0LED2-10 CBP 2-11 BCP 128 188 The present invention
0LED2- 11 CBP 2-9 BCP 130 212 本発明0LED2-11 CBP 2-9 BCP 130 212 Present invention
0LED2- 12 ACZ1 2-3 BCP 133 224 本発明0LED2-12 ACZ1 2-3 BCP 133 224 Present invention
0LED2- 13 ACZ2 2-3 BCP 132 223 本発明0LED2-13 ACZ2 2-3 BCP 132 223 Present invention
0LED2- 14 CBP 2-3 ACZ1 131 225 本発明0LED2-14 CBP 2-3 ACZ1 131 225 Present invention
0LED2-15 CBP 2-3 ACZ2 130 220 本発明0LED2-15 CBP 2-3 ACZ2 130 220 Present invention
0LED2- 16 ACZ1 2-11 BCP 131 218 本発明0LED2-16 ACZ1 2-11 BCP 131 218 Present invention
0LED2-17 ACZ2 2-11 BCP 131 212 本発明0LED2-17 ACZ2 2-11 BCP 131 212 Present invention
0LE02-18 CBP 2-11 ACZ1 130 220 本発明0LE02-18 CBP 2-11 ACZ1 130 220 Present invention
0LED2-19 CBP 2-11 ACZ2 130 219 本発明 0LED2-19 CBP 2-11 ACZ2 130 219 Present invention
[0226] 表 2から、本発明に係る金属錯体を用いて作製した有機 EL素子は比較有機 EL素 子に比べ、高い発光効率と、発光寿命の長寿命化が達成できることが明らかである。 [0226] From Table 2, it is clear that the organic EL device manufactured using the metal complex according to the present invention can achieve higher luminous efficiency and longer luminescent life than the comparative organic EL device.
[0227] 更に、カルボリン誘導体または該カルボリン誘導体のカルボリン環を構成する炭化 水素環の炭素原子の少なくとも一つが更に窒素原子で置換されている環構造を有 する誘導体を発光層に併用することにより、また、カルボリン誘導体または該カルボリ ン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが更に 窒素原子で置換されている環構造を有する誘導体を正孔阻止層に使用することによ り、更に本発明に記載の効果の向上が見られた。  [0227] Further, by using a carboline derivative or a derivative having a ring structure in which at least one of carbon atoms of a hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom in the light-emitting layer, Further, by using a carboline derivative or a derivative having a ring structure in which at least one carbon atom of a hydrocarbon ring constituting the carboline ring of the carbolin derivative is further substituted with a nitrogen atom, the hole blocking layer is used. Further, the effect described in the present invention was improved.
[0228] 実施例 3  [0228] Example 3
《有機 EL素子 OLED3 - 1の作製》  <Preparation of organic EL element OLED3-1>
陽極としてガラス上に ΙΤΟを 150nm成膜した基板（ΝΗテクノグラス社製： ΝΑ— 45 )にパターユングを行った後、この ITO透明電極を設けた透明支持基板を iso—プロ ピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、 UVオゾン洗浄を 5分間行 つに。 [0229] この透明支持基板を、市販の真空蒸着装置の基板ホルダーに固定し、一方、 5つ のタンタル製抵抗加熱ボートに、 m-MTDATXA, Hl、 Ir—12、 BCP、 Alqを各 々入れ、真空蒸着装置 (第 1真空槽）に取付けた。 After patterning on a substrate (ΝΗ-45, manufactured by Techno Glass Co., Ltd.) with 150 nm of ΙΤΟ deposited on glass as an anode, the transparent support substrate provided with this ITO transparent electrode was ultrasonically treated with iso-propyl alcohol. Wash, dry with dry nitrogen gas, and perform UV ozone cleaning for 5 minutes. [0229] This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while m-MTDATXA, Hl, Ir-12, BCP, and Alq were each placed in five tantalum resistance heating boats. , And attached to a vacuum evaporation system (first vacuum tank).
[0230] さらに、タンタル製抵抗加熱ボートにフッ化リチウムを、タングステン製抵抗加熱ボ ートにアルミニウムをそれぞれ入れ、真空蒸着装置の第 2真空槽に取り付けた。 [0230] Further, lithium fluoride was placed in a resistance heating boat made of tantalum and aluminum was placed in a resistance heating boat made of tungsten, and they were attached to a second vacuum tank of a vacuum evaporation apparatus.
[0231] まず、第 1の真空槽を 4 X 10— 4Paまで減圧した後、 m_MTDATXAの入った前記 加熱ボートに通電して加熱し、蒸着速度 0. InmZ秒〜 0. 2nm/秒で透明支持基 板に膜厚 40nmの厚さになるように蒸着し、正孔注入 Z輸送層を設けた。 [0231] First, after the vacuum of the first vacuum chamber to 4 X 10- 4 Pa, and heated by supplying an electric current to the boat containing M_MTDATXA, transparent at a deposition rate of 0. InmZ sec ~ 0. 2 nm / sec Evaporation was performed to a thickness of 40 nm on the support substrate, and a hole injection Z transport layer was provided.
[0232] さらに、 HIの入った前記加熱ボートと Ir_ 12の入ったボートをそれぞれ独立に通 電して発光ホストである HIと発光ドーパントである Ir— 12の蒸着速度が 100 : 7にな るように調節し膜厚 30nmの厚さになるように蒸着し、発光層を設けた。 [0232] Further, the heating boat containing HI and the boat containing Ir_12 are independently conducted, and the deposition rate of HI as the light emitting host and Ir-12 as the light emitting dopant becomes 100: 7. This was adjusted to a thickness of 30 nm, and a light emitting layer was provided.
[0233] ついで、 BCPの入った前記加熱ボートに通電して加熱し、蒸着速度 0. ：!〜 0. 2n m/秒で厚さ 10nmの正孔阻止層を設けた。さらに、 Alqの入った前記加熱ボートを 通電して加熱し、蒸着速度 0. lnm/秒〜 0. 2nm/秒で膜厚 20nmの電子輸送層 を設けた。 [0233] Next, the heating boat containing the BCP was energized and heated to provide a hole blocking layer having a thickness of 10 nm at a deposition rate of 0.2 to 0.2 nm / sec. Further, the heating boat containing Alq was heated by being energized to provide an electron transporting layer having a thickness of 20 nm at a deposition rate of 0.1 nm / sec to 0.2 nm / sec.
[0234] 次に、前記の如く電子輸送層まで製膜した素子を真空のまま第 2真空槽に移した 後、電子輸送層の上にステンレス鋼製の長方形穴あきマスクが配置されるように装置 外部からリモートコントロールして設置した。  [0234] Next, after the device formed as described above up to the electron transport layer was transferred to the second vacuum chamber while maintaining a vacuum, a rectangular perforated mask made of stainless steel was placed on the electron transport layer. Equipment Installed by remote control from outside.
[0235] 第 2真空槽を 2 X 10— 4Paまで減圧した後、フッ化リチウム入りのボートに通電して蒸 着速度 0. Olnm/秒〜 0. 02nm/秒で膜厚 0. 5nmの陰極バッファ一層を設け、 次いでアルミニウムの入ったボートに通電して蒸着速度 lnm/秒〜 2nm/秒で膜厚 150nmの陰極をつけた。さらにこの有機 EL素子を大気に接触させることなく窒素雰 囲気下のグローブボックス（純度 99. 999%以上の高純度窒素ガスで置換したグロ ーブボックス）へ移し、図 5に示したような内部を窒素で置換した封止構造にして、有 機 EL素子 OLED3— 1を作製した。なお、捕水剤である酸化バリウム 105は、アルド リッチ社製の高純度酸化バリウム粉末を、粘着剤付きのフッ素樹脂系半透過膜 (ミク 口テックス S -NTF8031Q 日東電工製）でガラス製封止缶 104に貼り付けたもの を予め準備して使用した。封止缶と有機 EL素子の接着には紫外線硬化型接着剤 1 07を用い、紫外線ランプを照射することで両者を接着し封止素子を作製した。図 5に おいて 101は透明電極を設けたガラス基板、 102が前記正孔注入/輸送層、発光 層、正孔阻止層、電子輸送層等からなる有機 EL層、 103は陰極を示す。 [0235] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, at a steam Chakusokudo 0. Olnm / sec ~ 0. 02nm / sec thickness 0. 5 nm of energizing the boat lithium fluoride-containing A cathode buffer layer was provided, and then a boat containing aluminum was energized to apply a 150 nm-thick cathode at a deposition rate of 1 nm / sec to 2 nm / sec. Furthermore, the organic EL device was transferred to a glove box (a glove box replaced with a high-purity nitrogen gas having a purity of 99.999% or more) in a nitrogen atmosphere without being brought into contact with the atmosphere. The organic EL element OLED3-1 was fabricated with the sealing structure replaced by. Barium oxide 105, a water-trapping agent, is made of high-purity barium oxide powder manufactured by Aldrich Co., Ltd., and sealed with a fluororesin semi-permeable membrane with adhesive (Mikuguchi Tex S-NTF8031Q manufactured by Nitto Denko). What was pasted on the can 104 was prepared in advance and used. UV curable adhesive for bonding cans and organic EL devices 1 Using 07, the two were adhered by irradiating an ultraviolet lamp to form a sealing element. In FIG. 5, 101 is a glass substrate provided with a transparent electrode, 102 is an organic EL layer composed of the hole injection / transport layer, light emitting layer, hole blocking layer, electron transport layer, etc., and 103 is a cathode.
[0236] 《有機 EL素子 OLED3 _ 2〜3 _ 23の作製》 [0236] << Preparation of Organic EL Element OLED3_2 ~ 3_23 >>
上記の有機 EL素子 OLED3— 1の作製において、表 3に記載のように、発光ホスト In the fabrication of the organic EL device OLED3-1, as described in Table 3,
、発光ドーパント及び正孔阻止材料を、各々変更した以外は同様にして、有機 EL素 子 OLED3 - 2〜3 _ 23を作製した。 The organic EL devices OLED3-2 to 3 _23 were produced in the same manner except that the luminescent dopant and the hole blocking material were changed.
[0237] 得られた有機£し素子〇1^^)3 _ 1〜3 _ 23にっぃて、外部取り出し量子効率につ レ、て実施例 1と同様の方法で評価を行った。 With respect to the obtained organic EL devices {1 ^^) 3_1 to 3_23, the external extraction quantum efficiency was evaluated in the same manner as in Example 1.
[0238] 《電圧上昇》 [0238] 《Voltage rise》
有機 EL素子 OLED3—：!〜 3— 23を 25°C、 2. 5mA/cm2の定電流条件下による 連続点灯を行い、初期輝度の半分の輝度になった時の駆動電圧の、初期度駆動電 圧からの上昇分を測定した。 Organic EL element OLED3—:! To 3-23 is continuously lit at 25 ° C and a constant current of 2.5 mA / cm2, and the initial drive voltage when the brightness reaches half of the initial brightness The rise from the drive voltage was measured.
[0239] なお、外部取り出し量子効率、電圧上昇は有機 EL素子 OLED3— 1を 100とした 時の相対値で表した。 [0239] The external extraction quantum efficiency and voltage rise were expressed as relative values when the organic EL element OLED3-1 was set to 100.
[0240] 得られた結果を表 3に示す。 [0240] The obtained results are shown in Table 3.
[0241] [表 3] [0241] [Table 3]
外部取リ出し External retrieval
素子 No. 発光ホスト 発光ドーパント 正孔阻止材料 電圧上昇 備 考  Device No. Emitting host Emitting dopant Hole blocking material Voltage rise Remarks
星" 率  Stars "rate
o o o o o o o o o o 0LED3-1 H1 I r-12 BCP 100 100 比 較  o o o o o o o o o o 0 LED3-1 H1 I r-12 BCP 100 100 Comparison
0LED3-2 H1 I r-13 BCP 102 98 比 較  0 LED3-2 H1 I r-13 BCP 102 98 Comparison
0LED3-3 H1 比較 1 BCP 101 105 比 較  0 LED3-3 H1 comparison 1 BCP 101 105 comparison
0LED3-4 H1 3-1 BCP 1 19 87 本発明  0LED3-4 H1 3-1 BCP 1 19 87 Present invention
0LED3-5 H1 3-7 BCP 1 14 90 本発明  0LED3-5 H1 3-7 BCP 1 14 90 The present invention
0LED3-6 H1 3-9 BCP 127 82 本発明  0LED3-6 H1 3-9 BCP 127 82 Present invention
0LED3-7 H1 3-11 BCP 122 85 本発明  0LED3-7 H1 3-11 BCP 122 85 The present invention
0LED3-8 H1 3-19 BCP 120 88 本発明  0LED3-8 H1 3-19 BCP 120 88 The present invention
0LED3-9 H1 3-25 BCP 1 17 90 本発明  0LED3-9 H1 3-25 BCP 1 17 90 Present invention
0LED3-10 H1 3-29 BCP 126 85 本発明  0LED3-10 H1 3-29 BCP 126 85 The present invention
H1 3-27 BCP 128 81 本発明  H1 3-27 BCP 128 81 The present invention
ACZ1 3-29 BCP 131 78 本発明  ACZ1 3-29 BCP 131 78 The present invention
ACZ2 3-29 BCP 131 79 本発明  ACZ2 3-29 BCP 131 79 The present invention
H1 3-29 ACZ1 132 77 本発明  H1 3-29 ACZ1 132 77 Invention
H1 3-29 ACZ2 130 78 本発明  H1 3-29 ACZ2 130 78 Present invention
ACZ1 3-27 BCP 130 76 本発明  ACZ1 3-27 BCP 130 76 Present invention
ACZ2 3-27 BCP 130 76 本発明  ACZ2 3-27 BCP 130 76 Present invention
H1 3-27 ACZ1 131 75 本発明  H1 3-27 ACZ1 131 75 Invention
H1 3-27 ACZ2 131 75 本発明  H1 3-27 ACZ2 131 75 The present invention
ACZ1 3-1 BCP 129 78 本発明  ACZ1 3-1 BCP 129 78 The present invention
ACZ2 3-7 BCP 125 77 本発明  ACZ2 3-7 BCP 125 77 Invention
H1 3-19 ACZ3 127 80 本発明  H1 3-19 ACZ3 127 80 The present invention
H1 3-25 ACZ3 130 80 本発明  H1 3-25 ACZ3 130 80 The present invention
[0242] 表 3から、本発明に係る金属錯体を用いて作製した有機 EL素子は比較有機 EL素 子に比べ、高い発光効率と、低い電圧上昇が達成できることが明らかである。  [0242] From Table 3, it is clear that the organic EL device manufactured using the metal complex according to the present invention can achieve higher luminous efficiency and lower voltage rise than the comparative organic EL device.
[0243] 更に、カルボリン誘導体または該カルボリン誘導体のカルボリン環を構成する炭化 水素環の炭素原子の少なくとも一つが更に窒素原子で置換されている環構造を有 する誘導体を発光層に併用することにより、また、カルボリン誘導体または該カルボリ ン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが更に 窒素原子で置換されている環構造を有する誘導体を正孔阻止層に使用することによ り、更に本発明に記載の効果の向上が見られた。  [0243] Further, by using a carboline derivative or a derivative having a ring structure in which at least one of carbon atoms of a hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom in the light emitting layer, Further, by using a carboline derivative or a derivative having a ring structure in which at least one carbon atom of a hydrocarbon ring constituting the carboline ring of the carbolin derivative is further substituted with a nitrogen atom, the hole blocking layer is used. Further, the effect described in the present invention was improved.
[0244] 実施例 4  [0244] Example 4
《有機 EL素子 OLED4 - 1の作製》  <Preparation of OLED 4-1 organic EL element>
実施例 3における発光層の作成において、発光ホストである HIと発光ドーパントで ある Ir— 12の蒸着速度を 100 : 7から、 100 : 4に変更した以外は実施例 3と同様にし て有機 EL素子 OLED4— 1を作成した。  An organic EL device was prepared in the same manner as in Example 3 except that the deposition rate of HI as a light-emitting host and Ir-12 as a light-emitting dopant was changed from 100: 7 to 100: 4 in forming the light-emitting layer in Example 3. OLED4-1 was created.
[0245] 《有機 EL素子 OLED4— 2〜4 19の作製》 上記の有機 EL素子 OLED4—1の作製において、表 4に記載のように、発光ホスト 、発光ドーパント及び正孔阻止材料を、各々変更した以外は同様にして、有機 EL素 子 OLED4— 2〜4 11を作製した。 [0245] << Preparation of Organic EL Element OLED4-2-419 >> In the preparation of the organic EL element OLED4-1, as described in Table 4, the organic EL elements OLED4-2 to 4-4 were prepared in the same manner except that the light emitting host, the light emitting dopant, and the hole blocking material were respectively changed. 11 were produced.
[0246] 得られた有機 EL素子 OLED4—：!〜 4— 19について、下記の評価を行った。 [0246] The following evaluations were performed on the obtained organic EL elements OLED4 ::! To 4-19.
[0247] 《外部取り出し量子効率》 [0247] 《External quantum efficiency》
有機 EL素子 OLED4—：!〜 4_ 19を室温（約23で〜25° 、 2. 5mA/cm2の定 電流条件下による点灯を行い、点灯開始直後の発光輝度 (U [cd/m2]を測定する ことにより、外部取り出し量子効率（ ）を算出した。ここで、発光輝度の測定は、 CS — 1000 (ミノルタ製）を用いた。また、外部取り出し量子効率は、有機 EL素子 OLED 4—1を 100とした時の相対値で表した。 Organic EL element OLED4—: Lights up! ~ 4_19 at room temperature (about 25 to 25 °, constant current of 2.5 mA / cm 2 , and emission luminance immediately after starting lighting (U [cd / m 2 ] The external extraction quantum efficiency () was calculated by measuring, where the emission luminance was measured using CS — 1000 (manufactured by Minolta), and the external extraction quantum efficiency was measured using the organic EL element OLED 4 — It was expressed as a relative value when 1 was taken as 100.
[0248] 《発光寿命》 [0248] 《Emission life》
有機£し素子〇1^：04_ 1〜4_ 19を室温下、 2. 5mA/cm2の定電流条件下によ る連続点灯を行い、初期輝度の半分の輝度になるのに要する時間（ τ / )を測定し Organic EL device 1 ^: 04_1 to 4_19 are continuously lit at room temperature under a constant current condition of 2.5 mA / cm 2 , and the time required to reach half the initial luminance (τ /)
1 2 た。また、発光寿命は、有機 EL素子 OLED4— 1を 100として、相対値で表した。  1 2 The light emission life was expressed as a relative value with the organic EL element OLED4-1 as 100.
[0249] 得られた結果を表 4に示す。 [0249] The obtained results are shown in Table 4.
[0250] [表 4] [0250] [Table 4]
外部取り出し 発光 ¾= External emission Flash 発 光 =
素子 No. 発光ホス 発光ド—パン 卜 正孔阻止材料 備 考 量子効率  Device No. Light-emitting host Light-emitting dopant Hole-blocking material Remarks Quantum efficiency
0LED4-1 HI lr-12 BCP 100 100 比 較 0 LED4-1 HI lr-12 BCP 100 100 Comparison
0LED4-2 HI lr-13 BCP 101 104 比 較0 LED4-2 HI lr-13 BCP 101 104 Comparison
0LE04-3 HI 比較 1 BCP 100 85 比 較0LE04-3 HI comparison 1 BCP 100 85 comparison
0LED4-4 HI 4-1 BCP 129 199 本発明0LED4-4 HI 4-1 BCP 129 199 The present invention
0LED4-5 HI 4-5 BCP 123 190 本発明0LED4-5 HI 4-5 BCP 123 190 The present invention
0LED4-6 HI 4-7 BCP 135 221 本発明0LED4-6 HI 4-7 BCP 135 221 The present invention
0LED4-7 H1 4-9 BCP 132 216 本発明0LED4-7 H1 4-9 BCP 132 216 Present invention
0LED4-8 H1 4-20 BCP 130 200 本発明 マ 0LED4-8 H1 4-20 BCP 130 200
0LE04-9 HI 4-21 BCP 134 220 本発明 0LE04-9 HI 4-21 BCP 134 220 The present invention
0LED4-10 H1 4-23 in in BCP 125 197 本発明0LED4-10 H1 4-23 in in BCP 125 197 Invention
0LED4-11 H1 BCP 133 215 本発明0LED4-11 H1 BCP 133 215 The present invention
0LED4-12 ACZI BCP 136 230 本発明0LED4-12 ACZI BCP 136 230 The present invention
0LE04-13 ACZ2 4-1 BCP 135 232 本発明0LE04-13 ACZ2 4-1 BCP 135 232 Present invention
0LED4-14 H1 4-1 ACZ1 133 233 本発明0LED4-14 H1 4-1 ACZ1 133 233 Present invention
0LED4-15 H1 4-1 ACZ2 132 234 本発明0LED4-15 H1 4-1 ACZ2 132 234 Present invention
0LED4-16 ACZI 4-1 BCP 135 245 本発明0LED4-16 ACZI 4-1 BCP 135 245 The present invention
0LED4-17 ACZ2 4-25 BCP 135 240 本発明0LED4-17 ACZ2 4-25 BCP 135 240 Present invention
0LED4-18 H1 ACZ1 136 241 本発明0LED4-18 H1 ACZ1 136 241 The present invention
0LED4-19 H1 ACZ2 135 239 本発明 0LED4-19 H1 ACZ2 135 239 Present invention
[0251] 表 4から、本発明に係る金属錯体を用いて作製した有機 EL素子は比較有機 EL素 子に比べ、高い発光効率と、発光寿命の長寿命化が達成できることが明らかである。 更に、カルボリン誘導体または該カルボリン誘導体のカルボリン環を構成する炭化水 素環の炭素原子の少なくとも一つが更に窒素原子で置換されている環構造を有する 誘導体を発光層に併用することにより、また、カルボリン誘導体または該カルボリン誘 導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが更に窒素 原子で置換されている環構造を有する誘導体を正孔阻止層に使用することにより、 更に本発明に記載の効果の向上が見られた。 [0251] From Table 4, it is clear that the organic EL device manufactured using the metal complex according to the present invention can achieve higher luminous efficiency and longer luminescent life than the comparative organic EL device. Further, by using a carboline derivative or a derivative having a ring structure in which at least one carbon atom of a hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom in the light emitting layer, The use of a derivative or a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom for the hole blocking layer further enhances the present invention. The described effect was improved.
[0252] 実施例 5 [0252] Example 5
《有機 EL素子 OLED5— 1の作製》  << Preparation of organic EL element OLED5-1 >>
陽極としてガラス上に ΙΤΟを 150nm成膜した基板（ΝΗテクノグラス社製： ΝΑ— 45 )にパターニングを行った後、この ITO透明電極を設けた透明支持基板を iso—プロ ピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、 UVオゾン洗浄を 5分間行 つに。 [0253] この透明支持基板を、市販の真空蒸着装置の基板ホルダーに固定し、一方、 5つ のタンタル製抵抗加熱ボートに、 m-MTDATXA, Hl、 Ir—12、 BCP、 Alqを各 After patterning the substrate (ΝΗ-45, manufactured by Techno Glass Co., Ltd.) on which 150 nm of ΙΤΟ was formed on glass as an anode, the transparent support substrate provided with the ITO transparent electrodes was ultrasonically cleaned with iso-propyl alcohol. Then, dry with dry nitrogen gas and perform UV ozone cleaning for 5 minutes. [0253] The transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while five tantalum resistance heating boats were charged with m-MTDATXA, Hl, Ir-12, BCP, and Alq.
3 々入れ、真空蒸着装置 (第 1真空槽）に取付けた。  Three of them were placed and attached to a vacuum evaporation device (first vacuum tank).
[0254] 更に、タンタル製抵抗加熱ボートにフッ化リチウムを、タングステン製抵抗加熱ボー トにアルミニウムをそれぞれ入れ、真空蒸着装置の第 2真空槽に取り付けた。 [0254] Further, lithium fluoride was placed in a resistance heating boat made of tantalum, and aluminum was placed in a resistance heating boat made of tungsten, and they were attached to a second vacuum tank of a vacuum evaporation apparatus.
[0255] まず、第 1の真空槽を 4 X 10— 4Paまで減圧した後、 m_MTDATXAの入った前記 加熱ボートに通電して加熱し、蒸着速度 0. InmZ秒〜 0. 2nm/秒で透明支持基 板に膜厚 30nmの厚さになるように蒸着し、正孔注入 Z輸送層を設けた。 [0255] First, after the vacuum of the first vacuum chamber to 4 X 10- 4 Pa, and heated by supplying an electric current to the boat containing M_MTDATXA, transparent at a deposition rate of 0. InmZ sec ~ 0. 2 nm / sec Evaporation was performed on the support substrate so as to have a thickness of 30 nm, and a hole injection Z transport layer was provided.
[0256] さらに、 HIの入った前記加熱ボートと Ir_ 12の入ったボートをそれぞれ独立に通 電して発光ホストである HIと発光ドーパントである Ir— 12の蒸着速度が 100 : 7にな るように調節し膜厚 30nmの厚さになるように蒸着し、発光層を設けた。 [0256] Further, the heating boat containing HI and the boat containing Ir_12 were independently passed, and the deposition rate of HI as the light emitting host and Ir-12 as the light emitting dopant became 100: 7. This was adjusted to a thickness of 30 nm, and a light emitting layer was provided.
[0257] ついで、 BCPの入った前記加熱ボートに通電して加熱し、蒸着速度 0. InmZ秒[0257] Next, the heating boat containing the BCP was energized and heated, and the evaporation rate was set to 0. InmZ seconds.
〜0. 2nm/秒で厚さ 10nmの正孔阻止層を設けた。更に、 Alqの入った前記加熱 A hole blocking layer having a thickness of 10 nm was provided at a thickness of 0.2 nm / sec. Further, the heating containing Alq
3  Three
ボートを通電して加熱し、蒸着速度 0. lnm/秒〜 0. 2nm/秒で膜厚 30nmの電子 輸送層を設けた。  The boat was energized and heated to provide an electron transport layer with a thickness of 30 nm at a deposition rate of 0.1 nm / sec to 0.2 nm / sec.
[0258] 次に、前記の如く電子輸送層まで製膜した素子を真空のまま第 2真空槽に移した 後、電子輸送層の上にステンレス鋼製の長方形穴あきマスクが配置されるように装置 外部からリモートコントロールして設置した。  [0258] Next, after the element formed as far as the electron transport layer as described above was transferred to a second vacuum chamber while maintaining a vacuum, a rectangular perforated mask made of stainless steel was arranged on the electron transport layer. Equipment Installed by remote control from outside.
[0259] 第 2真空槽を 2 X 10— 4Paまで減圧した後、フッ化リチウム入りのボートに通電して蒸 着速度 0. Olnm/秒〜 0. 02nm/秒で膜厚 0. 5nmの陰極バッファ一層を設け、 次いでアルミニウムの入ったボートに通電して蒸着速度 lnm/秒〜 2nm/秒で膜厚 150nmの陰極をつけた。さらにこの有機 EL素子を大気に接触させることなく窒素雰 囲気下のグローブボックス（純度 99. 999%以上の高純度窒素ガスで置換したグロ ーブボックス）へ移し、図 5に示したような内部を窒素で置換した封止構造にして、有 機 EL素子 OLED1 _ 1を作製した。 [0259] After decompression of the second vacuum chamber up to 2 X 10- 4 Pa, at a steam Chakusokudo 0. Olnm / sec ~ 0. 02nm / sec thickness 0. 5 nm of energizing the boat lithium fluoride-containing A cathode buffer layer was provided, and then a boat containing aluminum was energized to apply a 150 nm-thick cathode at a deposition rate of 1 nm / sec to 2 nm / sec. Furthermore, the organic EL element was transferred to a glove box (a glove box replaced with a high-purity nitrogen gas having a purity of 99.999% or more) in a nitrogen atmosphere without being brought into contact with the atmosphere. The organic EL element OLED1_1 was fabricated with the sealing structure replaced with.
[0260] 尚、捕水剤である酸化バリウム 105は、アルドリッチ社製の高純度酸化バリウム粉末 を、粘着剤付きのフッ素樹脂系半透過膜 (ミクロテックス S— NTF8031Q 日東電 ェ製)でガラス製封止缶 104に貼り付けたものを予め準備して使用した。封止缶と有 機 EL素子の接着には紫外線硬化型接着剤 107を用い、紫外線ランプを照射するこ とで両者を接着し封止素子を作製した。図 5において 101は透明電極を設けたガラス 基板、 102が前記正孔注入/輸送層、発光層、正孔阻止層、電子輸送層等からなる 有機 EL層、 103は陰極を示す。 [0260] In addition, barium oxide 105, a water-trapping agent, was obtained by using a high-purity barium oxide powder manufactured by Aldrich Co., Ltd. with a fluororesin semi-permeable membrane (Microtex S-NTF8031Q manufactured by Nitto Denki) with an adhesive. What was pasted on the sealing can 104 was prepared and used in advance. With sealed can The UV-curable adhesive 107 was used for bonding the EL device, and both were adhered by irradiating an ultraviolet lamp to produce a sealing element. In FIG. 5, reference numeral 101 denotes a glass substrate provided with a transparent electrode, 102 denotes an organic EL layer including the above-described hole injection / transport layer, light emitting layer, hole blocking layer, electron transport layer, and 103 denotes a cathode.
[0261] 《有機 EL素子 OLED5 _ 2〜5 _ 25の作製》 [0261] << Preparation of organic EL element OLED5_2 ~ 5_25 >>
上記の有機 EL素子 OLED5— 1の作製において、表 5に記載のように、発光ホスト In the fabrication of the organic EL device OLED5-1 described above, as shown in Table 5, the light-emitting host
、発光ドーパント及び正孔阻止材料を、各々変更した以外は同様にして、有機 EL素 子 OLED5 - 2〜5 _ 25を作製した。 In the same manner as above, except that the light emitting dopant and the hole blocking material were respectively changed, organic EL devices OLED5-2 to 5_25 were produced.
[0262] 得られた有機£し素子〇1^^)5 _ 1〜5 _ 25にっぃて、外部取り出し量子効率につ レ、て実施例 1と同様の方法で評価を行った。 [0262] The external extraction quantum efficiency was evaluated in the same manner as in Example 1 for the obtained organic electroluminescent devices {1 ^^) 5_1 to 5_25.
[0263] 《発光寿命》 [0263] 《Emission life》
有機 EL素子 OLED5—：!〜 5— 25を室温下、 2. 5mA/cm2の定電流条件下によ る連続点灯を行い、初期輝度の 90%の輝度になるのに要する時間（ τ / )を測定し Organic EL element OLED5—: Continuous lighting of! To 5-25 at room temperature under a constant current of 2.5 mA / cm2, and the time required to reach 90% of the initial luminance (τ / )
1 9 た。なお、外部取り出し量子効率は、有機 EL素子 OLED5— 1を 100とした時の相対 値、発光寿命は有機 EL素子 OLED5— 1を 100とした時の相対値で表した。  1 9 The external extraction quantum efficiency was expressed as a relative value when the organic EL element OLED5-1 was set to 100, and the emission life was expressed as a relative value when the organic EL element OLED5-1 was set to 100.
[0264] 得られた結果を表 5に示す。  [0264] Table 5 shows the obtained results.
[0265] [表 5] [0265] [Table 5]
外部取り出し 発先 ロロ Take out outside Lolo
素子 No. 発光ホスト 発光ドーパント 正孔阻止材料 備 考  Device No. Light emitting host Light emitting dopant Hole blocking material Remarks
o o o o o 量子効率 1 /9 )  o o o o o Quantum efficiency 1/9)
■ m m m m m 5—1 H1 l r -12 BCP 100 100 比 較  ■ mm m mm m m 5-1 H1 l r -12 BCP 100 100 Comparison
0LED5-2 H1 l r -13 BCP 102 103 比 較  0LED5-2 H1 l r -13 BCP 102 103 Comparison
o H1 比較 1 BCP 101 99 比 較 o H1 comparison 1 BCP 101 99 comparison
0LED5-4 H1 5-1 BCP 120 140 本発明 0LED5-4 H1 5-1 BCP 120 140 The present invention
0LED5-5 H1 5-2 BCP 120 150 本発明  0LED5-5 H1 5-2 BCP 120 150 The present invention
0LED5-6 H1 5-3 BCP 121 167 本発明  0LED5-6 H1 5-3 BCP 121 167 The present invention
0LED5-7 H1 5-4 BCP 120 175 本発明  0LED5-7 H1 5-4 BCP 120 175 Present invention
H1 5-9 BCP 122 141 本発明  H1 5-9 BCP 122 141 The present invention
0LED5-9 H1 5-12 BCP 118 170 本発明  0LED5-9 H1 5-12 BCP 118 170 The present invention
H1 5 -13 BCP 121 140 本発明  H1 5 -13 BCP 121 140 The present invention
0LED5 -11 H1 5-14 BCP 122 138 本発明  0LED5 -11 H1 5-14 BCP 122 138 The present invention
0LED5 -12 H1 5-15 BCP 120 160 本発明  0LED5 -12 H1 5-15 BCP 120 160 The present invention
0LED5 -13 H1 5-16 BCP 121 172 本発明  0LED5 -13 H1 5-16 BCP 121 172 Present invention
ACZ1 5 -9 BCP 124 190 本発明  ACZ1 5 -9 BCP 124 190 The present invention
ACZ2 5 -9 BCP 125 192 本発明  ACZ2 5 -9 BCP 125 192 The present invention
H1 5-9 ACZ1 124 190 本発明  H1 5-9 ACZ1 124 190 The present invention
0LED5 -17 H1 5-9 ACZ2 124 191 本発明  0 LED5 -17 H1 5-9 ACZ2 124 191 The present invention
0LED5 -18 ACZ1 5-4 BCP 123 191 本発明  0 LED5 -18 ACZ1 5-4 BCP 123 191 The present invention
0LED5 -19 ACZ2 5-4 BCP 124 193 本発明  0LED5 -19 ACZ2 5-4 BCP 124 193 The present invention
0LED5 -20 H1 5-4 ACZ1 124 195 本発明  0 LED5 -20 H1 5-4 ACZ1 124 195 Present invention
H1 5-4 ACZ2 124 199 本発明  H1 5-4 ACZ2 124 199 The present invention
H1 5 -2 ACZ1 122 188 本発明  H1 5 -2 ACZ1 122 188 The present invention
H1 5 -10 ACZ1 124 188 本発明  H1 5 -10 ACZ1 124 188 The present invention
0LED5 -24 H1 5-14 ACZ1 123 186 本発明  0LED5 -24 H1 5-14 ACZ1 123 186 The present invention
0LED5 -25 H1 5-16 ACZ1 122 197 本発明  0 LED5 -25 H1 5-16 ACZ1 122 197 The present invention
[0266] 表 5から、本発明に係る金属錯体を用いて作製した有機 EL素子は比較有機 EL素 子に比べ、高い発光効率と、発光寿命の長寿命化が達成できることが明らかである。 更に、カルボリン誘導体または該カルボリン誘導体のカルボリン環を構成する炭化水 素環の炭素原子の少なくとも一つが更に窒素原子で置換されている環構造を有する 誘導体を発光層に併用することにより、また、カルボリン誘導体または該カルボリン誘 導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが更に窒素 原子で置換されている環構造を有する誘導体を正孔阻止層に使用することにより、 更に本発明に記載の効果の向上が見られた。  [0266] From Table 5, it is clear that the organic EL device manufactured using the metal complex according to the present invention can achieve higher luminous efficiency and longer luminescent life than the comparative organic EL device. Further, by using a carboline derivative or a derivative having a ring structure in which at least one carbon atom of a hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom in the light emitting layer, The use of a derivative or a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom for the hole blocking layer further enhances the present invention. The described effect was improved.
[0267] 実施例 6 [0267] Example 6
《有機 EL素子 OLED6— 1の作製》  << Preparation of organic EL element OLED6-1 >>
実施例 3の有機 EL素子 3— 1の作製において、発光層形成時に、発光ホストである HIと発光ドーパントである Ir— 12の蒸着速度を 100 : 7から、 100 : 5に変更した以外 は同様にして有機 EL素子 OLED6— 1を作製した。 [0268] 《有機 EL素子 OLED6— 2 6— 20の作製》 In the fabrication of the organic EL device 3-1 of Example 3, the same procedure was performed except that the deposition rate of HI as the light emitting host and Ir-12 as the light emitting dopant was changed from 100: 7 to 100: 5 during the formation of the light emitting layer. Thus, an organic EL device OLED6-1 was produced. [0268] << Preparation of organic EL element OLED6-2 6-20 >>
上記の有機 EL素子 OLED6— 1の作製において、表 6に記載のように、発光ホスト 、発光ドーパント及び正孔阻止材料を、各々変更した以外は同様にして、有機 EL素 子 OLED6 _ 2 6 _ 20を作製した。得られた有機 EL素子 OLED6 _ 1 6 _ 20に っレ、て、外部取り出し量子効率にっレ、て実施例 1と同様の方法で評価を行った。  In the production of the organic EL element OLED6-1, as described in Table 6, the organic EL element OLED6_2_6 was prepared in the same manner except that the light emitting host, the light emitting dopant, and the hole blocking material were respectively changed. 20 were produced. Evaluation was performed in the same manner as in Example 1 for the obtained organic EL element OLED6 — 16 — 20 and for the external extraction quantum efficiency.
[0269] 《電圧上昇》  [0269] 《Voltage rise》
有機 EL素子 OLED6—：! 6— 20を 25°C 2. 5mA/cm2の定電流条件下による 連続点灯を行い、初期輝度の半分の輝度になった時の駆動電圧の、初期度駆動電 圧からの上昇分を測定した。 The organic EL element OLED6 :: 6-20 is continuously lit at 25 ° C at a constant current of 2.5 mA / cm 2 , and the initial drive voltage of the drive voltage when the brightness reaches half of the initial brightness The rise from pressure was measured.
[0270] 尚、外部取り出し量子効率、電圧上昇は有機 EL素子 OLED6— 1を 100とした時 の相対値で表した。  [0270] The external extraction quantum efficiency and voltage rise were expressed as relative values when the organic EL element OLED6-1 was set to 100.
[0271] [表 6]  [0271] [Table 6]
[0272] 表 6から、本発明に係る金属錯体を用いて作製した有機 EL素子は比較有機 EL素 子に比べ、高い発光効率と、低い電圧上昇が達成できることが明らかである。更に、 カルボリン誘導体または該カルボリン誘導体のカルボリン環を構成する炭化水素環 の炭素原子の少なくとも一つが更に窒素原子で置換されている環構造を有する誘導 体を発光層に併用することにより、また、カルボリン誘導体または該カルボリン誘導体 のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが更に窒素原子 で置換されている環構造を有する誘導体を正孔阻止層に使用することにより、更に 本発明に記載の効果の向上が見られた。 [0272] From Table 6, it is clear that the organic EL device manufactured using the metal complex according to the present invention can achieve higher luminous efficiency and lower voltage rise than the comparative organic EL device. Further, a derivative having a ring structure in which at least one of carbon atoms of a carboline derivative or a hydrocarbon ring constituting a carboline ring of the carboline derivative is further substituted with a nitrogen atom. In addition, the use of the compound in the light-emitting layer allows the carboline derivative or a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom to be a hole. Use of the blocking layer further improved the effects described in the present invention.
[0273] 実施例 7  [0273] Example 7
《フルカラー表示装置の作製》  << Production of full-color display device >>
(青色発光素子の作製）  (Production of blue light emitting element)
実施例 1の有機 EL素子 OLED1— 7を青色発光素子として用いた。  The organic EL element OLED1-7 of Example 1 was used as a blue light emitting element.
[0274] (緑色発光素子の作製）  [0274] (Production of green light-emitting element)
Ir_ lを緑色発光素子として用いた。  Ir_l was used as a green light emitting device.
[0275] (赤色発光素子の作製）  [0275] (Production of red light-emitting element)
Ir_ 9を赤色発光素子として用いた。  Ir_9 was used as a red light emitting element.
[0276] 上記で作製した、各々赤色、緑色、青色発光有機 EL素子を同一基板上に並置し、 図 1に記載のような形態を有するアクティブマトリクス方式フルカラー表示装置を作製 し、図 2には、作製した前記表示装置の表示部 Aの模式図のみを示した。即ち、同一 基板上に、複数の走査線 5及びデータ線 6を含む配線部と、並置した複数の画素 3 ( 発光の色が赤領域の画素、緑領域の画素、青領域の画素等）とを有し、配線部の走 查線 5及び複数のデータ線 6はそれぞれ導電材料からなり、走査線 5とデータ線 6は 格子状に直交して、直交する位置で画素 3に接続している（詳細は図示せず)。前記 複数画素 3は、それぞれの発光色に対応した有機 EL素子、アクティブ素子であるス イッチングトランジスタと駆動トランジスタそれぞれが設けられたアクティブマトリクス方 式で駆動されており、走査線 5から走查信号が印加されると、データ線 6から画像デ ータ信号を受け取り、受け取った画像データに応じて発光する。この様に各赤、緑、 青の画素を適宜、並置することによって、フルカラー表示装置を作製した。  [0276] The red, green, and blue light-emitting organic EL elements respectively manufactured above were juxtaposed on the same substrate, and an active matrix type full-color display device having the form shown in FIG. 1 was manufactured. Only a schematic view of the display unit A of the display device manufactured is shown. That is, on the same substrate, a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (pixels in a red region, pixels in a green region, pixels in a blue region, etc.) The scanning lines 5 and the plurality of data lines 6 of the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid and are connected to the pixels 3 at orthogonal positions. (Details not shown). The plurality of pixels 3 are driven by an active matrix method including an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal from a scanning line 5. When applied, it receives an image data signal from the data line 6 and emits light according to the received image data. Thus, a full-color display device was manufactured by juxtaposing the red, green, and blue pixels as appropriate.
[0277] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、且つ、 鮮明なフルカラー動画表示が得られることが判った。  [0277] It was found that by driving the full-color display device, a high luminance, high durability, and a clear full-color moving image display can be obtained.
[0278] 実施例 8  [0278] Example 8
《フルカラー表示装置の作製》 実施例 7の青色発光素子の作製において、有機 EL素子 OLED1— 7を、有機 EL 素子 OLED2— 7に変更した以外は同様にしてフルカラー表示装置を作製した。 << Production of full-color display device >> A full-color display device was produced in the same manner as in the production of the blue light-emitting device of Example 7, except that the organic EL elements OLED1-7 were changed to the organic EL elements OLED2-7.
[0279] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、且つ、 鮮明なフルカラー動画表示が得られることが判った。 [0279] By driving the full-color display device, it was found that high luminance, high durability, and clear full-color moving image display were obtained.
[0280] 実施例 9 [0280] Example 9
《フルカラー表示装置の作製》  << Production of full-color display device >>
実施例 7の青色発光素子の作製において、有機 EL素子 OLED1— 7を、有機 EL 素子 OLED3— 4  In the fabrication of the blue light emitting device of Example 7, the organic EL device OLED1-7 was replaced with the organic EL device OLED3-4.
に変更した以外は同様にしてフルカラー表示装置を作製した。  A full-color display device was produced in the same manner except that the above was changed.
[0281] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、且つ、 鮮明なフルカラー動画表示が得られることが判った。 [0281] It was found that by driving the full-color display device, a high luminance, high durability, and a clear full-color moving image display can be obtained.
[0282] 実施例 10 [0282] Example 10
《フルカラー表示装置の作製》  << Production of full-color display device >>
実施例 7の青色発光素子の作製において、有機 EL素子 OLED1— 7を、有機 EL 素子 OLED4— 4に変更した以外は同様にしてフルカラー表示装置を作製した。  A full-color display device was fabricated in the same manner as in the fabrication of the blue light-emitting device of Example 7, except that the organic EL devices OLED1-7 were changed to the organic EL devices OLED4-4.
[0283] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、且つ、 鮮明なフルカラー動画表示が得られることが判った。 [0283] By driving the full-color display device, it was found that high luminance, high durability, and clear full-color moving image display were obtained.
[0284] 実施例 11 Example 11
《フルカラー表示装置の作製》  << Production of full-color display device >>
実施例 7の青色発光素子の作製において、有機 EL素子 OLED1— 7を、有機 EL 素子 OLED5— 4に変更した以外は同様にしてフルカラー表示装置を作製した。  A full-color display device was produced in the same manner as in the production of the blue light-emitting device of Example 7, except that the organic EL elements OLED1-7 were changed to the organic EL elements OLED5-4.
[0285] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、且つ、 鮮明なフルカラー動画表示が得られることが判った。 [0285] By driving the full-color display device, it was found that a high luminance, high durability, and a clear full-color moving image display could be obtained.
[0286] 実施例 12 [0286] Example 12
《フルカラー表示装置の作製》  << Production of full-color display device >>
実施例 7の青色発光素子の作製において、有機 EL素子 OLED1— 7を、有機 EL 素子 OLED6— 5に変更した以外は同様にしてフルカラー表示装置を作製した。  A full-color display device was produced in the same manner as in the production of the blue light-emitting device of Example 7, except that the organic EL elements OLED1-7 were changed to the organic EL elements OLED6-5.
[0287] 該フルカラー表示装置を駆動することにより、輝度が高ぐ高耐久性を有し、且つ、 鮮明なフルカラー動画表示が得られることが判った。 [0287] By driving the full-color display device, the device has high durability with high luminance, and It was found that a clear full-color moving image display could be obtained.
[0288] 実施例 13  Example 13
《白色発光素子および白色照明装置の作製》  << Production of white light emitting element and white lighting device >>
実施例 1の透明電極基板の電極を 20mm X 20mmにパターユングし、その上に実 施例 1と同様に正孔注入/輸送層としてひ一NPDを 25nmの厚さで製膜し、さらに、 CBPの入った前記加熱ボートと本発明化合物 1 _ 5の入ったボートおよび Ir_ 9の入 つたボートをそれぞれ独立に通電して発光ホストである CBPと発光ドーパントである 本発明化合物 1 _ 5および Ir_ 9の蒸着速度が 100 : 5 : 0. 6になるように調節し膜厚 30nmの厚さになるように蒸着し、発光層を設けた。  The electrode of the transparent electrode substrate of Example 1 was patterned into 20 mm X 20 mm, and a single NPD was formed thereon as a hole injection / transport layer with a thickness of 25 nm as in Example 1; The above-mentioned heated boat containing CBP, the boat containing Compound 1-5 of the present invention, and the boat containing Ir_9 are supplied with current independently, and CBP as a light-emitting host and Compounds 1_5 and Ir_5 as light-emitting dopants of the present invention. The deposition rate of 9 was adjusted so as to be 100: 5: 0.6, and the deposition was performed so as to have a thickness of 30 nm, thereby providing a light emitting layer.
[0289] ついで、 BCPを 10nm製膜して正孔阻止層を設けた。更に、 Alqを 40nmで製膜し 電子輸送層を設けた。 Next, a hole blocking layer was provided by forming a film of BCP to a thickness of 10 nm. Further, a film of Alq was formed at a thickness of 40 nm to provide an electron transport layer.
[0290] 次に、実施例 1と同様に、電子注入層の上にステンレス鋼製の透明電極とほぼ同じ 形状の正方形穴あきマスクを設置し、陰極バッファ一層としてフッ化リチウム 0. 5nm 及び陰極としてアルミニウム 150nmを蒸着製膜した。  [0290] Next, as in Example 1, a square perforated mask having substantially the same shape as the transparent electrode made of stainless steel was placed on the electron injection layer, and lithium fluoride 0.5 nm and the cathode were used as a cathode buffer layer. Was formed by vapor deposition of aluminum with a thickness of 150 nm.
[0291] この素子を実施例 1と同様な方法および同様な構造の封止缶を具備させ平面ラン プを作製した。図 6に平面ランプの模式図を示した。図 6 (a)に平面模式を図 6 (b)に 断面模式図を示す。 [0291] This device was equipped with a sealing can having the same method and the same structure as in Example 1 to produce a planar lamp. Fig. 6 shows a schematic diagram of a flat lamp. Fig. 6 (a) shows a schematic plan view and Fig. 6 (b) shows a schematic cross-sectional view.
[0292] この平面ランプに通電したところほぼ白色の光が得られ、照明装置として使用でき ること力ゎカゝつた。  [0292] When this flat lamp was energized, almost white light was obtained, and it could be used as a lighting device.
[0293] 実施例 14 [0293] Example 14
《白色発光素子および白色照明装置の作製》  << Production of white light emitting element and white lighting device >>
実施例 13の白色発光素子の作製において、本発明化合物 1—5を 2— 7に変更し た以外は実施例 13と同様にして白色照明装置を作製した。  A white lighting device was manufactured in the same manner as in Example 13, except that the compound of the present invention 1-5 was changed to 2-7 in the manufacture of the white light-emitting device of Example 13.
[0294] この平面ランプに通電したところほぼ白色の光が得られ、照明装置として使用でき ることがわかった。 [0294] When the flat lamp was energized, almost white light was obtained, indicating that it could be used as a lighting device.
[0295] 実施例 15 [0295] Example 15
《白色発光素子および白色照明装置の作製》  << Production of white light emitting element and white lighting device >>
実施例 13の白色発光素子の作製にぉレ、て、本発明化合物 1一 5を 3— 2に変更し た以外は実施例 13と同様にして白色照明装置を作製した。 In preparation of the white light emitting device of Example 13, the present compound 115 was changed to 3-2. A white lighting device was produced in the same manner as in Example 13 except for the above.
[0296] この平面ランプに通電したところほぼ白色の光が得られ、照明装置として使用でき ること力ゎカゝつた。 [0296] When the flat lamp was energized, almost white light was obtained, and it could be used as a lighting device.
[0297] 実施例 16 Example 16
《白色発光素子および白色照明装置の作製》  << Production of white light emitting element and white lighting device >>
実施例 13の白色発光素子の作製において、化合物 1—5を 4— 4に変更した以外 は実施例 13と同様にして白色照明装置を作製した。  A white lighting device was manufactured in the same manner as in Example 13, except that Compounds 1-5 were changed to 4-4 in the preparation of the white light-emitting device of Example 13.
[0298] この平面ランプに通電したところほぼ白色の光が得られ、照明装置として使用でき ることがわかった。 [0298] When the flat lamp was energized, almost white light was obtained, and it was found that the lamp could be used as a lighting device.
[0299] 実施例 17 [0299] Example 17
《白色発光素子および白色照明装置の作製》  << Production of white light emitting element and white lighting device >>
実施例 13の白色発光素子の作製にぉレ、て、化合物 1 _ 5を 5 - 1に変更した以外 は実施例 13と同様にして白色照明装置を作製した。  A white light emitting device was produced in the same manner as in Example 13, except that Compound 1_5 was changed to 5-1 in preparation of the white light-emitting element of Example 13.
[0300] この平面ランプに通電したところほぼ白色の光が得られ、照明装置として使用でき ること力ゎカゝつた。 [0300] When the flat lamp was energized, almost white light was obtained, and it could be used as a lighting device.
[0301] 実施例 18 [0301] Example 18
《白色発光素子および白色照明装置の作製》  << Production of white light emitting element and white lighting device >>
実施例 13の白色発光素子の作製にぉレ、て、化合物 1 5を 6— 5に変更した以外 は実施例 13と同様にして白色照明装置を作製した。  A white light device was produced in the same manner as in Example 13 except that Compound 15 was changed to 6-5 in preparation of the white light-emitting device of Example 13.
[0302] この平面ランプに通電したところほぼ白色の光が得られ、照明装置として使用でき ること力ゎカゝつた。 [0302] When the flat lamp was energized, almost white light was obtained, and it could be used as a lighting device.
[0303] 実施例 19 [0303] Example 19
《有機 EL素子 OLED7 _ 1~7- 13の作製》  << Preparation of organic EL element OLED7_1 ~ 7-13 >>
実施例 1において、発光ドーパントを Ir_ lに変更し、正孔阻止材料を表 7に記載の ように変更した以外は同様にして、有機 EL素子 OLED7—：!〜 7— 13を作製した。  Organic EL devices OLED7— :! to 7-13 were prepared in the same manner as in Example 1, except that the light emitting dopant was changed to Ir_l and the hole blocking material was changed as shown in Table 7.
[0304] 得られた各々の素子の外部取り出し量子効率、発光寿命の測定も実施例 1に記載 の方法と同様にして行った。  [0304] The external extraction quantum efficiency and emission lifetime of each of the obtained devices were also measured in the same manner as in Example 1.
[0305] この時、いずれも OLED7— 1の値を 100として、各有機 EL素子試料の値を相対値 で表した。得られた結果を表 7に示す。 [0305] At this time, the value of each organic EL element sample was a relative value, with the value of OLED7-1 as 100. It was represented by Table 7 shows the obtained results.
[0306] [表 7] [Table 7]
[0307] 表 7から、本発明の有機 EL素子材料を正孔阻止材料に用いた有機 EL素子は比 較素子に比べ、高い発光効率と、発光寿命が得られることがわかった。なお、本発明 の素子の発 [0307] From Table 7, it was found that the organic EL device using the organic EL device material of the present invention as a hole blocking material has higher luminous efficiency and luminous life than the comparative device. Note that the device of the present invention was developed.
光色は全て緑色だった。  The light colors were all green.
産業上の利用可能性  Industrial applicability
[0308] 本発明により、有機 EL素子用に有用な有機 EL素子材料が得られ、該有機 EL素 子材料を用いることにより、発光波長が制御され、高い発光効率を示し、且つ、発光 寿命の長い有機 EL素子、照明装置及び表示装置を提供することができた。 According to the present invention, an organic EL device material useful for an organic EL device is obtained. By using the organic EL device material, the emission wavelength is controlled, high luminous efficiency is exhibited, and the luminescent lifetime is improved. A long organic EL element, a lighting device, and a display device can be provided.

Claims

請求の範囲 The scope of the claims
下記一般式（1)または、該一般式（1)の互変異性体を部分構造として有する金属錯 体、下記一般式 (2)または、該一般式 (2)の互変異性体を部分構造として有する金 属錯体、下記一般式 (3)または、該一般式 (3)の互変異性体を部分構造として有す る金属錯体、下記一般式 (4)または、該一般式 (4)の互変異性体を部分構造として 有する金属錯体、下記一般式 (5)または、該一般式 (5)の互変異性体を部分構造と して有する金属錯体、または、下記一般式 (6)または、該一般式 (6)の互変異性体を 部分構造として有する金属錯体であることを特徴とする有機エレクト口ルミネッセンス 素子材料。 A metal complex having the following general formula (1) or a tautomer of the general formula (1) as a partial structure; a tautomer of the following general formula (2) or the tautomer of the general formula (2) having a partial structure A metal complex having the following general formula (3) or a tautomer of the general formula (3) as a partial structure; a metal complex having the following general formula (4) or a general formula (4): A metal complex having a tautomer as a partial structure, a metal complex having the following general formula (5) or a tautomer of the general formula (5) as a partial structure, or a metal complex having the following general formula (6) or An organic electroluminescent device material comprising a metal complex having a tautomer of the general formula (6) as a partial structure.
[化 1] 一般式 (1)[Formula 1] General formula (1)
〔式中、 Z11は、芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 R 、R 、R は、各々水素原子または置換基を表す。 M は、元素周期表 [In the formula, Z11 represents an atom group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. R 1, R 2 and R 3 each represent a hydrogen atom or a substituent. M is the periodic table of the elements
11 12 13 11 における 8族〜 10族の金属を表す。〕  11 12 13 11 represents a metal belonging to Group 8 to Group 10. ]
[化 2] 一般式 (2)[Formula 2] General formula (2)
〔式中、 Z21は芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 R 、R 、R は、各々水素原子または置換基を表す。 M は、元素周期表 における 8族〜 10族の金属を表す。〕 [In the formula, Z21 represents an atom group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocycle. R 1, R 2 and R 3 each represent a hydrogen atom or a substituent. M is the periodic table of the elements Represents a metal belonging to Group 8 to Group 10. ]
[化 3] 一般式 (3)[Formula 3] General formula (3)
〔式中、 Z31は、芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 X 、Χ 、Χ は、各々置換基を有してもよい炭素原子または窒素原子を  [In the formula, Z31 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X, Χ and Χ each represent a carbon atom or a nitrogen atom which may have a substituent.
31 32 33  31 32 33
表すが、少なくとも 2つは、窒素原子または一 N (R ) - (ここで、 Rは、水素原子また Where at least two are nitrogen atoms or one N (R)-(where R is a hydrogen atom or
3 3  3 3
は置換基を表す。）を表す。 C は炭素原子を表す。 M は、元素周期表における 8族 Represents a substituent. ). C represents a carbon atom. M is group 8 in the periodic table
31 31  31 31
〜10族の金属を表す。 C と Nとの間の結合、 Nと X との間の結合、 X と X との間の  Represents a metal of Group 10 Bond between C and N, bond between N and X, between X and X
31 33 32 33 結合、 X と X との間の結合、 C と X との間の結合は、各々単結合または二重結合 31 33 32 33 bond, bond between X and X, bond between C and X are single bond or double bond, respectively
31 32 31 31 31 32 31 31
を表す。〕 Represents. ]
[化 4] 一般式 (4) [Formula 4] General formula (4)
I！ '.\ I! '. \
-43 ^41 ：'  -43 ^ 41: '
,、Z4、1ノ'  ,, Z4, 1 '
〔式中、 Z41は、芳香族複素環を形成するのに必要な原子群を表す。 X 、X は置換 [In the formula, Z41 represents an atom group necessary for forming an aromatic heterocyclic ring. X and X are replaced
41 42 基を有してもよい炭素原子または窒素原子を表すが、その少なくとも 1つは、窒素原 子または N (R ) （ここで、 Rは、水素原子または置換基を表す。 )を表す。 M は  41 42 represents a carbon atom or a nitrogen atom which may have a group, at least one of which represents a nitrogen atom or N (R) (where R represents a hydrogen atom or a substituent). . M is
4 4 41 4 4 41
、元素周期表における 8族〜 10族の金属を表す。 C 、C 、C は、各々炭素原子を Represents a metal belonging to Groups 8 to 10 of the periodic table. C 1, C 2 and C 3 each have a carbon atom
41 42 43  41 42 43
表す。 M は、元素周期表における 8族〜 10族の金属を表す。 C と C との間の結合 Represent. M represents a metal belonging to Groups 8 to 10 in the periodic table. Coupling between C and C
41 41 42  41 41 42
、C と X との間の結合、 X と X との間の結合、 X と C との間の結合、 C と C との 間の結合は、単結合または二重結合を表す。〕 , The bond between C and X, the bond between X and X, the bond between X and C, the bond between C and C The bond between represents a single bond or a double bond. ]
[化 5] 一般式 (5) [Formula 5] General formula (5)
〔式中、 Z51は、芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 X は、酸素原子または硫黄原子を表す。 R 、R は、水素原子または置  [In the formula, Z51 represents an atomic group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X represents an oxygen atom or a sulfur atom. R and R are a hydrogen atom or
51 51 52 換基を表す。 M は、元素周期表における 8族〜 10族の金属を表す。〕  51 51 52 represents a substituent. M represents a metal belonging to Groups 8 to 10 in the periodic table. ]
51  51
[化 6]  [Formula 6]
一般式 (6) General formula (6)
61、  61,
ズ 61 Z61
〔式中、 Z61は、芳香族炭化水素環または芳香族複素環を形成するのに必要な原子 群を表す。 X 、Χ 、Χ は、各々置換基を有してもよい炭素原子または窒素原子を [In the formula, Z61 represents an atom group necessary for forming an aromatic hydrocarbon ring or an aromatic heterocyclic ring. X, Χ and Χ each represent a carbon atom or a nitrogen atom which may have a substituent.
61 62 63  61 62 63
表すが、少なくとも 1つは窒素原子を表す。 Μ は、元素周期表における 8族〜 10族  And at least one of them represents a nitrogen atom. Μ is group 8 to group 10 in the periodic table
61  61
の金属を表す。〕  Represents a metal. ]
[2] 上記一般式（1)または、該一般式（1)の互変異性体を部分構造として有する金属錯 体であることを特徴とする請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素 子材料。  [2] The organic electroluminescent device according to claim 1, which is a metal complex having the above general formula (1) or a tautomer of the general formula (1) as a partial structure. Element material.
[3] 上記一般式（1)または、該一般式（1)の互変異性体を部分構造として有する金属錯 体において Z11が芳香族複素環を形成するのに必要な原子群を表すことを特徴と する請求の範囲第 2項に記載の有機エレクト口ルミネッセンス素子材料。 [4] 上記一般式 (2)または、該一般式 (2)の互変異性体を部分構造として有する金属錯 体であることを特徴とする請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素 子材料。 [3] In the above-described general formula (1) or a metal complex having a tautomer of the general formula (1) as a partial structure, Z11 represents an atom group necessary for forming an aromatic heterocyclic ring. 3. The organic electroluminescent device material according to claim 2, wherein the material is an organic electroluminescent device. [4] The organic electroluminescent according to claim 1, which is a metal complex having the above-mentioned general formula (2) or a tautomer of the general formula (2) as a partial structure. Element material.
[5] 上記一般式 (3)または、該一般式 (3)の互変異性体を部分構造として有する金属錯 体であることを特徴とする請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素 子材料。  [5] The organic electroluminescent material according to claim 1, which is a metal complex having the above-mentioned general formula (3) or a tautomer of the general formula (3) as a partial structure. Element material.
[6] 上記一般式 (3)または、該一般式 (3)の互変異性体を部分構造として有する金属錯 体において、 X は置換基を有してもよい炭素原子を表し、 X 、X は窒素原子又は  [6] In the above general formula (3) or a metal complex having a tautomer of the general formula (3) as a partial structure, X represents a carbon atom which may have a substituent; Is a nitrogen atom or
31 32 33  31 32 33
_N (R ) _ (ここで、 Rは、水素原子または置換基を表す。）を表すことを特徴とする _N (R) _ (where R represents a hydrogen atom or a substituent)
3 3 3 3
請求の範囲第 5項に記載の有機エレクト口ルミネッセンス素子材料。  6. The organic electroluminescent device material according to claim 5.
[7] 上記一般式 (4)または、該一般式 (4)の互変異性体を部分構造として有する金属錯 体であることを特徴とする請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素 子材料。 [7] The organic electroluminescent device according to claim 1, which is a metal complex having the above-mentioned general formula (4) or a tautomer of the general formula (4) as a partial structure. Element material.
[8] 上記一般式 (5)または、該一般式 (5)の互変異性体を部分構造として有する金属錯 体であることを特徴とする請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素 子材料。  [8] The organic electroluminescent device according to claim 1, which is a metal complex having the above general formula (5) or a tautomer of the general formula (5) as a partial structure. Element material.
[9] 上記一般式 (5)または、該一般式 (5)の互変異性体を部分構造として有する金属錯 体において X 、硫黄原子を表すことを特徴とする請求の範囲第 8項に記載の有機  [9] The method according to claim 8, wherein in the metal complex having the general formula (5) or a tautomer of the general formula (5) as a partial structure, X and a sulfur atom are represented. Organic
51  51
エレクト口ルミネッセンス素子材料。  Elect port luminescence element material.
[10] 上記一般式 (6)または、該一般式 (6)の互変異性体を部分構造として有する金属錯 体であることを特徴とする請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素 子材料。  [10] The organic electroluminescence according to claim 1, which is a metal complex having the above-mentioned general formula (6) or a tautomer of the general formula (6) as a partial structure. Element material.
[11] 上記一般式 (6)または、該一般式 (6)の互変異性体を部分構造として有する金属錯 体において、 X 、X の少なくとも 1つは窒素原子を表すことを特徴とする請求の範囲  [11] In the metal complex having the general formula (6) or a tautomer of the general formula (6) as a partial structure, at least one of X 1 and X 2 represents a nitrogen atom. Range
61 63  61 63
第 10項に記載の有機エレクト口ルミネッセンス素子材料。  Item 11. The organic electroluminescent device material according to Item 10.
[12] 前記一般式（1)において、 M 力 S、イリジウムまたは白金であることを特徴とする請求 [12] In the general formula (1), M is S, iridium or platinum.
11  11
の範囲第 2項に記載の有機エレクト口ルミネッセンス素子材料。  3. The organic electroluminescent device material according to item 2, wherein
[13] 上記一般式（1)において Z11が芳香族複素環を形成するのに必要な原子群を表す ことを特徴とする請求の範囲第 12項に記載の有機エレクト口ルミネッセンス素子材料 [14] 前記一般式（2)において、 M 1 イリジウムまたは白金であることを特徴とする請求 [13] In the above general formula (1), Z11 represents an atomic group necessary for forming an aromatic heterocyclic ring. 13. The organic electroluminescent device material according to claim 12, wherein the material is M 1 iridium or platinum in the general formula (2).
21  twenty one
の範囲第 4項に記載の有機エレクト口ルミネッセンス素子材料。  Item 5. The organic electorescence luminescent element material according to Item 4.
[15] 前記一般式（3)において、 Μ 力 イリジウムまたは白金であることを特徴とする請求 [15] In the above general formula (3), the metal is iridium or platinum.
31  31
の範囲第 5項に記載の有機エレクト口ルミネッセンス素子材料。  Item 6. The organic electroluminescent device material according to Item 5, wherein
[16] 上記一般式（3)において、 X は置換基を有してもよい炭素原子を表し、 X 、Χ は窒 [16] In the general formula (3), X represents a carbon atom which may have a substituent, and X and Χ represent nitrogen atoms.
31 32 33 素原子又は— N (R ) - (ここで、 Rは、水素原子または置換基を表す。）を表すこと  31 32 33 represents an atom or —N (R) — (where R represents a hydrogen atom or a substituent)
3 3  3 3
を特徴とする請求の範囲第 15項に記載の有機エレクト口ルミネッセンス素子材料。  16. The organic electroluminescent device material according to claim 15, wherein:
[17] 前記一般式 (4)において、 M 力 イリジウムまたは白金であることを特徴とする請求 [17] In the above general formula (4), M is iridium or platinum.
41  41
の範囲第 7項に記載の有機エレクト口ルミネッセンス素子材料。  Item 8. The organic electroluminescent device material according to item 7, wherein
[18] 前記一般式（5)において、 M 力 イリジウムまたは白金であることを特徴とする請求 [18] In the above general formula (5), M is iridium or platinum.
51  51
の範囲第 8項に記載の有機エレクト口ルミネッセンス素子材料。  Item 9. An organic electorescence luminescent element material according to Item 8.
[19] 上記一般式（5)において X 、硫黄原子を表すことを特徴とする請求の範囲第 18 [19] The method according to claim 18, wherein in the general formula (5), X represents a sulfur atom.
51  51
項に記載の有機エレクト口ルミネッセンス素子材料。  Item 4. The organic electroluminescent device material according to item 1.
[20] 前記一般式（6)において、 M 1 イリジウムまたは白金であることを特徴とする請求 [20] In the above general formula (6), M 1 is iridium or platinum.
61  61
の範囲第 10項に記載の有機エレクト口ルミネッセンス素子材料。  Item 11. The organic electroluminescent device material according to Item 10, wherein
[21] 上記一般式 (6)において、 X 、Χ の少なくとも 1つは窒素原子を表すことを特徴とす [21] In the above general formula (6), at least one of X and Χ represents a nitrogen atom.
61 63  61 63
る請求の範囲第 20項に記載の有機エレクト口ルミネッセンス素子材料。  21. The organic electroluminescent device material according to claim 20.
[22] 請求の範囲第 1項に記載の有機エレクト口ルミネッセンス素子材料を含有することを 特徴とする有機エレクト口ルミネッセンス素子。 [22] An organic electroluminescent device comprising the organic electroluminescent device material according to claim 1.
[23] 構成層として発光層を有し、該発光層が請求の範囲第 1項に記載の有機エレクト口 ノレミネッセンス素子材料を含有することを特徴とする有機エレクト口ルミネッセンス素 子。 [23] An organic electroluminescent device comprising a light emitting layer as a constituent layer, wherein the light emitting layer contains the organic electroluminescent device according to claim 1.
[24] 構成層として正孔阻止層を有し、該正孔阻止層が請求の範囲第 1項に記載の有機 エレクト口ルミネッセンス素子材料を含有することを特徴とする有機エレクト口ルミネッ センス素子。  [24] An organic electroluminescent device having a hole blocking layer as a constituent layer, wherein the hole blocking layer contains the organic electroluminescent device material according to claim 1.
[25] 構成層として発光層を有し、該発光層が、カルボリン誘導体または該カルボリン誘導 体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが窒素原子で 置換されている環構造を有する誘導体を含有することを特徴とする請求の範囲第 22 項に記載の有機エレクト口ルミネッセンス素子。 [25] A light emitting layer as a constituent layer, wherein the light emitting layer is a carboline derivative or a carboline derivative. 23. The organic electroluminescence according to claim 22, wherein said organic electroluminescent material contains a derivative having a ring structure in which at least one of carbon atoms of a hydrocarbon ring constituting a carboline ring of the body is substituted with a nitrogen atom. element.
[26] 構成層として正孔阻止層を有し、該正孔阻止層が、カルボリン誘導体または該カル ボリン誘導体のカルボリン環を構成する炭化水素環の炭素原子の少なくとも一つが 窒素原子で置換されている環構造を有する誘導体を含有することを特徴とする請求 の範囲第 22項に記載の有機エレクト口ルミネッセンス素子。 [26] A hole blocking layer as a constituent layer, wherein the hole blocking layer is formed by replacing at least one of carbon atoms of a carboline derivative or a hydrocarbon ring constituting a carboline ring of the carboline derivative with a nitrogen atom. 23. The organic electroluminescent device according to claim 22, further comprising a derivative having a ring structure.
[27] 請求の範囲第 22項に記載の有機エレクト口ルミネッセンス素子を有することを特徴と する表示装置。 [27] A display device comprising the organic electroluminescent device according to claim 22.
[28] 請求の範囲第 22項に記載の有機エレクト口ルミネッセンス素子を有することを特徴と する照明装置。  [28] A lighting device comprising the organic electorophore luminescent device according to claim 22.
PCT/JP2005/010552 2004-06-17 2005-06-09 Organic electroluminescent device material, organic electroluminescent device, display and illuminating device WO2005123873A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2006514709A JP4894513B2 (en) 2004-06-17 2005-06-09 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004179627 2004-06-17
JP2004-179627 2004-06-17

Publications (1)

Publication Number Publication Date
WO2005123873A1 true WO2005123873A1 (en) 2005-12-29

Family

ID=35509662

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2005/010552 WO2005123873A1 (en) 2004-06-17 2005-06-09 Organic electroluminescent device material, organic electroluminescent device, display and illuminating device

Country Status (2)

Country Link
JP (1) JP4894513B2 (en)
WO (1) WO2005123873A1 (en)

Cited By (513)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007029466A1 (en) * 2005-09-06 2007-03-15 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
WO2007052431A1 (en) * 2005-10-31 2007-05-10 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
JP2007189001A (en) * 2006-01-12 2007-07-26 Konica Minolta Holdings Inc Organic electroluminescence element, material thereof, display device, and luminaire
JP2007204592A (en) * 2006-02-01 2007-08-16 Showa Denko Kk Polymer light-emitting material, organic electroluminescent element and display
WO2007097153A1 (en) * 2006-02-20 2007-08-30 Konica Minolta Holdings, Inc. Organic electroluminescence element material, organic electroluminescence element, display device and illuminating device
JP2008101114A (en) * 2006-10-19 2008-05-01 Konica Minolta Holdings Inc Organic electroluminescent element material, organic electroluminescent element, display and illuminating device
WO2008072539A1 (en) * 2006-12-11 2008-06-19 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
EP1998388A1 (en) 2006-03-23 2008-12-03 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
EP1998387A1 (en) 2006-03-17 2008-12-03 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
JPWO2008035664A1 (en) * 2006-09-20 2010-01-28 コニカミノルタホールディングス株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
JPWO2008035571A1 (en) * 2006-09-20 2010-01-28 コニカミノルタホールディングス株式会社 Organic electroluminescence device
US8007927B2 (en) 2007-12-28 2011-08-30 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8040053B2 (en) 2008-02-09 2011-10-18 Universal Display Corporation Organic light emitting device architecture for reducing the number of organic materials
US8053770B2 (en) 2008-10-14 2011-11-08 Universal Display Corporation Emissive layer patterning for OLED
WO2012070596A1 (en) * 2010-11-26 2012-05-31 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
CN102648205A (en) * 2009-12-08 2012-08-22 佳能株式会社 Novel iridium complex and organic light-emitting device including the same
WO2012124622A1 (en) 2011-03-14 2012-09-20 東レ株式会社 Light-emitting element material and light-emitting element
JP2012188357A (en) * 2011-03-08 2012-10-04 Nagasaki Univ Metal complex, light-emitting device, and display device
WO2012153725A1 (en) 2011-05-12 2012-11-15 東レ株式会社 Light-emitting element material and light-emitting element
JP2013010752A (en) * 2011-06-03 2013-01-17 Semiconductor Energy Lab Co Ltd Organometallic complex, organic light-emitting element, light-emitting device, electronic equipment and lighting system
US8367223B2 (en) 2008-11-11 2013-02-05 Universal Display Corporation Heteroleptic phosphorescent emitters
US8377332B2 (en) 2008-06-10 2013-02-19 Basf Se Transition metal complexes and use thereof in organic light emitting diodes—III
US8384068B2 (en) 2007-10-02 2013-02-26 Basf Se Use of acridine derivatives as matrix materials and/or electron blockers in OLEDs
US8410270B2 (en) 2008-06-10 2013-04-02 Basf Se Transition metal complexes and use thereof in organic light-emitting diodes V
US8440326B2 (en) 2008-06-30 2013-05-14 Universal Display Corporation Hole transport materials containing triphenylene
US8492006B2 (en) 2011-02-24 2013-07-23 Universal Display Corporation Germanium-containing red emitter materials for organic light emitting diode
EP2623508A1 (en) 2012-02-02 2013-08-07 Konica Minolta Advanced Layers, Inc. Iridium complex compound, organic electroluminescent element material, organic electroluminescent element, illumination device and display device
US8513658B2 (en) 2008-09-04 2013-08-20 Universal Display Corporation White phosphorescent organic light emitting devices
US8519384B2 (en) 2008-09-03 2013-08-27 Universal Display Corporation Phosphorescent materials
US8545996B2 (en) 2009-11-02 2013-10-01 The University Of Southern California Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes
US8557400B2 (en) 2009-04-28 2013-10-15 Universal Display Corporation Iridium complex with methyl-D3 substitution
US8563737B2 (en) 2011-02-23 2013-10-22 Universal Display Corporation Methods of making bis-tridentate carbene complexes of ruthenium and osmium
US8586204B2 (en) 2007-12-28 2013-11-19 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
WO2014017484A1 (en) 2012-07-25 2014-01-30 東レ株式会社 Light emitting element material and light emitting element
US8652656B2 (en) 2011-11-14 2014-02-18 Universal Display Corporation Triphenylene silane hosts
US8659036B2 (en) 2011-06-17 2014-02-25 Universal Display Corporation Fine tuning of emission spectra by combination of multiple emitter spectra
WO2014030666A1 (en) 2012-08-24 2014-02-27 コニカミノルタ株式会社 Transparent electrode, electronic device, and method for manufacturing transparent electrode
US8692241B1 (en) 2012-11-08 2014-04-08 Universal Display Corporation Transition metal complexes containing triazole and tetrazole carbene ligands
US8709615B2 (en) 2011-07-28 2014-04-29 Universal Display Corporation Heteroleptic iridium complexes as dopants
US8716484B1 (en) 2012-12-05 2014-05-06 Universal Display Corporation Hole transporting materials with twisted aryl groups
US8722205B2 (en) 2009-03-23 2014-05-13 Universal Display Corporation Heteroleptic iridium complex
US8742657B2 (en) 2010-06-11 2014-06-03 Universal Display Corporation Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications
US8748011B2 (en) 2011-02-23 2014-06-10 Universal Display Corporation Ruthenium carbene complexes for OLED material
US8748012B2 (en) 2011-05-25 2014-06-10 Universal Display Corporation Host materials for OLED
US8778511B2 (en) 2008-12-12 2014-07-15 Universal Display Corporation OLED stability via doped hole transport layer
US8795850B2 (en) 2011-05-19 2014-08-05 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology
US8815415B2 (en) 2008-12-12 2014-08-26 Universal Display Corporation Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes
US8822708B2 (en) 2007-08-08 2014-09-02 Universal Display Corporation Benzo-fused thiophene / triphenylene hybrid materials
WO2014138912A1 (en) * 2013-03-13 2014-09-18 Queen's University At Kingston Luminescent compounds and methods of using same
WO2014157618A1 (en) 2013-03-29 2014-10-02 コニカミノルタ株式会社 Organic electroluminescent element, and lighting device and display device which are provided with same
WO2014157494A1 (en) 2013-03-29 2014-10-02 コニカミノルタ株式会社 Material for organic electroluminescent elements, organic electroluminescent element, display device and lighting device
US8859110B2 (en) 2008-06-20 2014-10-14 Basf Se Cyclic phosphazene compounds and use thereof in organic light emitting diodes
US8866377B2 (en) 2006-12-28 2014-10-21 Universal Display Corporation Long lifetime phosphorescent organic light emitting device (OLED) structures
US8871361B2 (en) 2011-02-23 2014-10-28 Universal Display Corporation Tetradentate platinum complexes
US8884316B2 (en) 2011-06-17 2014-11-11 Universal Display Corporation Non-common capping layer on an organic device
US8883322B2 (en) 2011-03-08 2014-11-11 Universal Display Corporation Pyridyl carbene phosphorescent emitters
US8889864B2 (en) 2006-02-10 2014-11-18 Universal Display Corporation Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
US8927749B2 (en) 2013-03-07 2015-01-06 Universal Display Corporation Organic electroluminescent materials and devices
US8926119B2 (en) 2011-08-04 2015-01-06 Universal Display Corporation Extendable light source with variable light emitting area
US8927308B2 (en) 2011-05-12 2015-01-06 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
US8932734B2 (en) 2010-10-08 2015-01-13 Universal Display Corporation Organic electroluminescent materials and devices
US8946697B1 (en) 2012-11-09 2015-02-03 Universal Display Corporation Iridium complexes with aza-benzo fused ligands
US8952362B2 (en) 2012-08-31 2015-02-10 The Regents Of The University Of Michigan High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion
US8952363B2 (en) 2009-01-16 2015-02-10 Universal Display Corporation Organic electroluminescent materials and devices
US8963132B2 (en) 2010-03-25 2015-02-24 Universal Display Corporation Solution processable doped triarylamine hole injection materials
US8968887B2 (en) 2010-04-28 2015-03-03 Universal Display Corporation Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
US8969592B2 (en) 2012-01-10 2015-03-03 Universal Display Corporation Heterocyclic host materials
US8987451B2 (en) 2012-01-03 2015-03-24 Universal Display Corporation Synthesis of cyclometallated platinum(II) complexes
US9005771B2 (en) 2009-05-12 2015-04-14 Universal Display Corporation 2-azatriphenylene materials for organic light emitting diodes
US9005772B2 (en) 2011-02-23 2015-04-14 Universal Display Corporation Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials
US9034483B2 (en) 2008-09-16 2015-05-19 Universal Display Corporation Phosphorescent materials
US9040962B2 (en) 2010-04-28 2015-05-26 Universal Display Corporation Depositing premixed materials
US9054344B2 (en) 2010-01-20 2015-06-09 Universal Display Corporation Electroluminescent devices for lighting applications
US9054323B2 (en) 2012-03-15 2015-06-09 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
US9059412B2 (en) 2012-07-19 2015-06-16 Universal Display Corporation Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs
US9118017B2 (en) 2012-02-27 2015-08-25 Universal Display Corporation Host compounds for red phosphorescent OLEDs
US9130177B2 (en) 2011-01-13 2015-09-08 Universal Display Corporation 5-substituted 2 phenylquinoline complexes materials for light emitting diode
US9142786B2 (en) 2007-03-08 2015-09-22 Universal Display Corporation Phosphorescent materials
US9156870B2 (en) 2010-02-25 2015-10-13 Universal Display Corporation Phosphorescent emitters
US9166175B2 (en) 2012-11-27 2015-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US9163174B2 (en) 2012-01-04 2015-10-20 Universal Display Corporation Highly efficient phosphorescent materials
US9175211B2 (en) 2010-03-03 2015-11-03 Universal Display Corporation Phosphorescent materials
US9184399B2 (en) 2012-05-04 2015-11-10 Universal Display Corporation Asymmetric hosts with triaryl silane side chains
US9181270B2 (en) 2014-02-28 2015-11-10 Universal Display Corporation Method of making sulfide compounds
US9190621B2 (en) 2007-03-08 2015-11-17 Universal Display Corporation Materials for organic light emitting diode
US9190623B2 (en) 2012-11-20 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9190620B2 (en) 2014-03-01 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9193745B2 (en) 2011-11-15 2015-11-24 Universal Display Corporation Heteroleptic iridium complex
US9196860B2 (en) 2012-12-04 2015-11-24 Universal Display Corporation Compounds for triplet-triplet annihilation upconversion
US9209411B2 (en) 2012-12-07 2015-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US9212197B2 (en) 2011-05-19 2015-12-15 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants
US9217004B2 (en) 2011-11-21 2015-12-22 Universal Display Corporation Organic light emitting materials
US9224958B2 (en) 2013-07-19 2015-12-29 Universal Display Corporation Organic electroluminescent materials and devices
US9231218B2 (en) 2012-07-10 2016-01-05 Universal Display Corporation Phosphorescent emitters containing dibenzo[1,4]azaborinine structure
US9252377B2 (en) 2011-07-14 2016-02-02 Universal Display Corporation Inorganic hosts in OLEDs
US9252363B2 (en) 2012-10-04 2016-02-02 Universal Display Corporation Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers
US9287513B2 (en) 2012-09-24 2016-03-15 Universal Display Corporation Organic electroluminescent materials and devices
JP2016036032A (en) * 2015-09-14 2016-03-17 コニカミノルタ株式会社 Organic electroluminescent element, display device and illuminating device
US9293712B2 (en) 2013-10-11 2016-03-22 Universal Display Corporation Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same
US9306179B2 (en) 2013-11-08 2016-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US9312499B1 (en) 2015-01-05 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9312505B2 (en) 2012-09-25 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9318710B2 (en) 2012-07-30 2016-04-19 Universal Display Corporation Organic electroluminescent materials and devices
US9324949B2 (en) 2013-07-16 2016-04-26 Universal Display Corporation Organic electroluminescent materials and devices
CN105524114A (en) * 2015-12-24 2016-04-27 石家庄诚志永华显示材料有限公司 Series of deep blue metal iridium phosphorescence OLED materials
US9359549B2 (en) 2009-04-06 2016-06-07 Universal Display Corporation Organic electroluminescent materials and devices
US9386657B2 (en) 2012-03-15 2016-07-05 Universal Display Corporation Organic Electroluminescent materials and devices
JP2016520576A (en) * 2013-04-29 2016-07-14 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Transition metal complexes with carbene ligands and their use in OLEDs
US9397302B2 (en) 2014-10-08 2016-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US9397310B2 (en) 2011-07-14 2016-07-19 Universal Display Corporation Organice electroluminescent materials and devices
US9397312B2 (en) 2011-05-11 2016-07-19 Universal Display Corporation Process for fabricating metal bus lines for OLED lighting panels
US9397309B2 (en) 2014-03-13 2016-07-19 Universal Display Corporation Organic electroluminescent devices
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
US9419225B2 (en) 2013-03-14 2016-08-16 Universal Display Corporation Organic electroluminescent materials and devices
US9435021B2 (en) 2010-07-29 2016-09-06 University Of Southern California Co-deposition methods for the fabrication of organic optoelectronic devices
US9444075B2 (en) 2014-11-26 2016-09-13 Universal Display Corporation Emissive display with photo-switchable polarization
US9450198B2 (en) 2014-04-15 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US9450195B2 (en) 2014-12-17 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US9455417B2 (en) 2011-12-13 2016-09-27 Universal Display Corporation Split electrode for organic devices
US9455411B2 (en) 2008-09-25 2016-09-27 Universal Display Corporation Organic electroluminescent materials and devices
US9461254B2 (en) 2012-01-03 2016-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US9478758B1 (en) 2015-05-08 2016-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US9484541B2 (en) 2014-10-20 2016-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US9493698B2 (en) 2011-08-31 2016-11-15 Universal Display Corporation Organic electroluminescent materials and devices
US9502672B2 (en) 2012-06-21 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US9502656B2 (en) 2014-02-24 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US9512136B2 (en) 2012-11-26 2016-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US9512355B2 (en) 2011-12-09 2016-12-06 Universal Display Corporation Organic light emitting materials
US9537106B2 (en) 2013-05-09 2017-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US9540329B2 (en) 2012-07-19 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9543532B2 (en) 2010-06-11 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9553274B2 (en) 2013-07-16 2017-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US9590180B2 (en) 2007-06-23 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9590195B2 (en) 2014-02-28 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9590194B2 (en) 2014-02-14 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9634264B2 (en) 2012-11-09 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US9647227B2 (en) 2005-04-13 2017-05-09 Universal Display Corporation Organic light emitting devices
US9647217B2 (en) 2014-02-24 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9647218B2 (en) 2013-11-14 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9647221B2 (en) 2011-07-14 2017-05-09 Universal Display Corporation Organic light-emitting devices
US9653691B2 (en) 2012-12-12 2017-05-16 Universal Display Corporation Phosphorescence-sensitizing fluorescence material system
US9663544B2 (en) 2012-07-25 2017-05-30 Universal Display Corporation Organic electroluminescent materials and devices
US9673406B2 (en) 2009-05-20 2017-06-06 Universal Display Corporation Metal complexes with boron-nitrogen heterocycle containing ligands
US9673401B2 (en) 2013-06-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9670404B2 (en) 2012-06-06 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9673407B2 (en) 2014-02-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9685617B2 (en) 2012-11-09 2017-06-20 Universal Display Corporation Organic electronuminescent materials and devices
US9691993B2 (en) 2014-04-09 2017-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US9711730B2 (en) 2015-01-25 2017-07-18 Universal Display Corporation Organic electroluminescent materials and devices
EP3200255A2 (en) 2016-01-06 2017-08-02 Konica Minolta, Inc. Organic electroluminescent element, method for producing organic electroluminescent element, display, and lighting device
US9725476B2 (en) 2012-07-09 2017-08-08 Universal Display Corporation Silylated metal complexes
US9735373B2 (en) 2013-06-10 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9735378B2 (en) 2013-09-09 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9741941B2 (en) 2014-04-29 2017-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US9748500B2 (en) 2015-01-15 2017-08-29 Universal Display Corporation Organic light emitting materials
US9748503B2 (en) 2013-09-13 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US9755159B2 (en) 2014-01-23 2017-09-05 Universal Display Corporation Organic materials for OLEDs
US9755164B2 (en) 2011-06-08 2017-09-05 Universal Display Corporation Organic electroluminescent materials and devices
US9761807B2 (en) 2013-07-15 2017-09-12 Universal Display Corporation Organic light emitting diode materials
US9761814B2 (en) 2014-11-18 2017-09-12 Universal Display Corporation Organic light-emitting materials and devices
US9773986B2 (en) 2009-11-19 2017-09-26 The University Of Southern California Copper(I)-carbene complexes and organic electroluminescent devices
US9773985B2 (en) 2012-05-21 2017-09-26 Universal Display Corporation Organic electroluminescent materials and devices
US9780316B2 (en) 2015-03-16 2017-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US9783564B2 (en) 2011-07-25 2017-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US9812653B2 (en) 2013-11-28 2017-11-07 Samsung Electronics Co., Ltd. Carbazole compound and organic light-emitting device including the same
US9812657B2 (en) 2014-01-07 2017-11-07 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
US9831447B2 (en) 2013-10-08 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9831437B2 (en) 2013-08-20 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9847498B2 (en) 2014-04-14 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9847497B2 (en) 2014-02-18 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9847496B2 (en) 2013-12-23 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9853229B2 (en) 2013-10-23 2017-12-26 University Of Southern California Organic electroluminescent materials and devices
US9859510B2 (en) 2015-05-15 2018-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US9865824B2 (en) 2013-11-07 2018-01-09 Industrial Technology Research Institute Organometallic compound, organic light-emitting device, and lighting device employing the same
US9871214B2 (en) 2015-03-23 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
US9871212B2 (en) 2014-11-14 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
US9876173B2 (en) 2013-12-09 2018-01-23 Universal Display Corporation Organic electroluminescent materials and devices
US9882151B2 (en) 2014-11-14 2018-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US9899612B2 (en) 2006-12-08 2018-02-20 Universal Display Corporation Organic electroluminescent materials and devices
CN107722060A (en) * 2017-09-30 2018-02-23 南京邮电大学 A kind of fluorenyl tetrazole complex of iridium and its preparation method and application
US9905784B2 (en) 2013-11-15 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US9911931B2 (en) 2014-06-26 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9911928B2 (en) 2015-03-19 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9929357B2 (en) 2014-07-22 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9929353B2 (en) 2014-04-02 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9929361B2 (en) 2015-02-16 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9929360B2 (en) 2016-07-08 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9935277B2 (en) 2014-01-30 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US9932359B2 (en) 2013-08-30 2018-04-03 University Of Southern California Organic electroluminescent materials and devices
US9935276B2 (en) 2013-02-21 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US9954180B2 (en) 2010-08-20 2018-04-24 Universal Display Corporation Bicarbazole compounds for OLEDs
US9978961B2 (en) 2014-01-08 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US9978956B2 (en) 2015-07-15 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US9978958B2 (en) 2012-08-24 2018-05-22 Universal Display Corporation Phosphorescent emitters with phenylimidazole ligands
US9997712B2 (en) 2013-03-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US10003033B2 (en) 2014-02-18 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US10003034B2 (en) 2013-09-30 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US10008677B2 (en) 2011-01-13 2018-06-26 Universal Display Corporation Materials for organic light emitting diode
US10008679B2 (en) 2014-04-14 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US10033004B2 (en) 2015-06-01 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US10038151B2 (en) 2014-11-12 2018-07-31 Universal Display Corporation Organic electroluminescent materials and devices
US10043987B2 (en) 2014-09-29 2018-08-07 Universal Display Corporation Organic electroluminescent materials and devices
US10056565B2 (en) 2013-11-20 2018-08-21 Universal Display Corporation Organic electroluminescent materials and devices
US10069090B2 (en) 2012-11-20 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US10074806B2 (en) 2013-08-20 2018-09-11 Universal Display Corporation Organic electroluminescent materials and devices
US10079349B2 (en) 2011-05-27 2018-09-18 Universal Display Corporation Organic electroluminescent materials and devices
US10109799B2 (en) 2015-05-21 2018-10-23 Universal Display Corporation Organic electroluminescent materials and devices
US10121975B2 (en) 2013-07-03 2018-11-06 Universal Display Corporation Organic electroluminescent materials and devices
US10135008B2 (en) 2014-01-07 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10135006B2 (en) 2016-01-04 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10135007B2 (en) 2014-09-29 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US10147892B2 (en) 2010-12-07 2018-12-04 The University Of Southern California Organic electroluminescent materials and devices
US10144867B2 (en) 2015-02-13 2018-12-04 Universal Display Corporation Organic electroluminescent materials and devices
US10153445B2 (en) 2016-11-21 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10153443B2 (en) 2016-07-19 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10158089B2 (en) 2011-05-27 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
US10177316B2 (en) 2015-02-09 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US10177318B2 (en) 2015-10-29 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US10181564B2 (en) 2015-08-26 2019-01-15 Universal Display Corporation Organic electroluminescent materials and devices
US10199581B2 (en) 2013-07-01 2019-02-05 Universal Display Corporation Organic electroluminescent materials and devices
US10199582B2 (en) 2013-09-03 2019-02-05 University Of Southern California Organic electroluminescent materials and devices
US10205105B2 (en) 2016-08-15 2019-02-12 Universal Display Corporation Organic electroluminescent materials and devices
US10211413B2 (en) 2012-01-17 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US10208026B2 (en) 2014-03-18 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
CN109422775A (en) * 2017-08-21 2019-03-05 三星显示有限公司 Organo-metallic compound, organic luminescent device and organic light emitting apparatus
US10236458B2 (en) 2016-10-24 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10236456B2 (en) 2016-04-11 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10256427B2 (en) 2014-04-15 2019-04-09 Universal Display Corporation Efficient organic electroluminescent devices
US10256411B2 (en) 2015-05-21 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10253252B2 (en) 2014-12-30 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10256419B2 (en) 2014-05-08 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10270046B2 (en) 2015-03-06 2019-04-23 Universal Display Corporation Organic electroluminescent materials and devices
US10276809B2 (en) 2016-04-05 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US10297770B2 (en) 2015-03-27 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US10301338B2 (en) 2014-05-08 2019-05-28 Universal Display Corporation Organic electroluminescent materials and devices
US10340464B2 (en) 2016-11-10 2019-07-02 Universal Display Corporation Organic electroluminescent materials and devices
US10355227B2 (en) 2013-12-16 2019-07-16 Universal Display Corporation Metal complex for phosphorescent OLED
US10355222B2 (en) 2015-02-06 2019-07-16 Universal Display Corporation Organic electroluminescent materials and devices
US10361381B2 (en) 2015-09-03 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US10388892B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10388893B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10403830B2 (en) 2014-05-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10403825B2 (en) 2014-02-27 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10400163B2 (en) 2013-02-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10403826B2 (en) 2015-05-07 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10411199B2 (en) 2012-12-12 2019-09-10 Samsung Electronics Co., Ltd. Organometallic complexes, and organic electroluminescent device and display using the same
US10411200B2 (en) 2014-08-07 2019-09-10 Universal Display Corporation Electroluminescent (2-phenylpyridine)iridium complexes and devices
US10411201B2 (en) 2014-11-12 2019-09-10 Universal Display Corporation Organic electroluminescent materials and devices
US10418569B2 (en) 2015-01-25 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10418568B2 (en) 2015-06-01 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10418562B2 (en) 2015-02-06 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10457864B2 (en) 2016-02-09 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US10461260B2 (en) 2014-06-03 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US10457699B2 (en) 2014-05-02 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US10468609B2 (en) 2016-06-02 2019-11-05 Universal Display Corporation Organic electroluminescent materials and devices
US10476010B2 (en) 2015-11-30 2019-11-12 Universal Display Corporation Organic electroluminescent materials and devices
US10490753B2 (en) 2016-12-15 2019-11-26 Universal Display Corporation Organic electroluminescent materials and devices
US10505127B2 (en) 2016-09-19 2019-12-10 Universal Display Corporation Organic electroluminescent materials and devices
US10522769B2 (en) 2015-08-18 2019-12-31 Universal Display Corporation Organic electroluminescent materials and devices
US10529931B2 (en) 2015-03-24 2020-01-07 Universal Display Corporation Organic Electroluminescent materials and devices
US10566552B2 (en) 2016-04-13 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US10566546B2 (en) 2014-07-14 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US10566547B2 (en) 2016-07-11 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US10593890B2 (en) 2015-04-06 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US10593892B2 (en) 2015-10-01 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US10600967B2 (en) 2016-02-18 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US10600966B2 (en) 2015-02-27 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US10608188B2 (en) 2017-09-11 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US10608186B2 (en) 2016-09-14 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US10608185B2 (en) 2016-10-17 2020-03-31 Univeral Display Corporation Organic electroluminescent materials and devices
US10629820B2 (en) 2017-01-18 2020-04-21 Universal Display Corporation Organic electroluminescent materials and devices
US10636983B2 (en) 2014-05-08 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US10636978B2 (en) 2014-12-30 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US10644251B2 (en) 2013-12-04 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
US10644247B2 (en) 2015-02-06 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
US10651403B2 (en) 2016-06-20 2020-05-12 Universal Display Corporation Organic electroluminescent materials and devices
US10662196B2 (en) 2016-11-17 2020-05-26 Universal Display Corporation Organic electroluminescent materials and devices
US10672997B2 (en) 2016-06-20 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US10672998B2 (en) 2017-03-23 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US10680183B2 (en) 2015-02-15 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10680187B2 (en) 2016-09-23 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10680188B2 (en) 2016-11-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10686140B2 (en) 2016-06-20 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
US10686143B2 (en) 2015-03-05 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
DE102013200085B4 (en) 2012-01-06 2020-06-18 Universal Display Corporation Highly efficient phosphorescent materials
US10707423B2 (en) 2014-02-21 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US10707427B2 (en) 2016-02-09 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US10720587B2 (en) 2016-07-19 2020-07-21 Universal Display Corporation Organic electroluminescent materials and devices
US10727423B2 (en) 2016-06-20 2020-07-28 Universal Display Corporation Organic electroluminescent materials and devices
US10741780B2 (en) 2017-03-10 2020-08-11 Universal Display Corporation Organic electroluminescent materials and devices
US10749113B2 (en) 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10745431B2 (en) 2017-03-08 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10770664B2 (en) 2015-09-21 2020-09-08 Universal Display Corporation Organic electroluminescent materials and devices
US10777749B2 (en) 2015-05-07 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
US10777754B2 (en) 2017-04-11 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
US10790455B2 (en) 2017-05-18 2020-09-29 Universal Display Corporation Organic electroluminescent materials and devices
US10804475B2 (en) 2017-01-11 2020-10-13 Universal Display Corporation Organic electroluminescent materials and devices
US10811618B2 (en) 2016-12-19 2020-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US10822361B2 (en) 2017-02-22 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10825997B2 (en) 2015-06-25 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10822362B2 (en) 2017-05-11 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10833276B2 (en) 2016-11-21 2020-11-10 Universal Display Corporation Organic electroluminescent materials and devices
US10840458B2 (en) 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10840459B2 (en) 2017-05-18 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10844085B2 (en) 2017-03-29 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US10847728B2 (en) 2015-10-01 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US10854826B2 (en) 2014-10-08 2020-12-01 Universal Display Corporation Organic electroluminescent compounds, compositions and devices
US10862046B2 (en) 2017-03-30 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10862054B2 (en) 2016-06-20 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10862055B2 (en) 2017-05-05 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10868261B2 (en) 2014-11-10 2020-12-15 Universal Display Corporation Organic electroluminescent materials and devices
US10873037B2 (en) 2017-03-28 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US10870668B2 (en) 2017-05-05 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US10873036B2 (en) 2015-07-07 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US10897016B2 (en) 2016-11-14 2021-01-19 Universal Display Corporation Organic electroluminescent materials and devices
US10910570B2 (en) 2017-04-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US10910577B2 (en) 2017-03-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US10923667B2 (en) 2017-03-08 2021-02-16 Samsung Electronics Co., Ltd. Organometallic compound, composition containing the organometallic compound, and organic light-emitting device including the organometallic compound
US10930866B2 (en) 2013-07-25 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10930864B2 (en) 2017-05-10 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10930862B2 (en) 2017-06-01 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10934293B2 (en) 2017-05-18 2021-03-02 Universal Display Corporation Organic electroluminescent materials and devices
US10944062B2 (en) 2017-05-18 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10941170B2 (en) 2017-05-03 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10944060B2 (en) 2017-05-11 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10950803B2 (en) 2014-10-13 2021-03-16 Universal Display Corporation Compounds and uses in devices
US10957870B2 (en) 2012-09-07 2021-03-23 Universal Display Corporation Organic light emitting device
US10957861B2 (en) 2015-12-29 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US10957866B2 (en) 2016-06-30 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US10964904B2 (en) 2017-01-20 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US10964893B2 (en) 2016-11-17 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US10971687B2 (en) 2017-12-14 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US10968226B2 (en) 2017-06-23 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US10975113B2 (en) 2017-04-21 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US10978647B2 (en) 2017-02-15 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US10991895B2 (en) 2015-10-06 2021-04-27 Universal Display Corporation Organic electroluminescent materials and devices
US10998507B2 (en) 2015-11-23 2021-05-04 Universal Display Corporation Organic electroluminescent materials and devices
US11011709B2 (en) 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
US11018309B2 (en) 2015-08-03 2021-05-25 Universal Display Corporation Organic electroluminescent materials and devices
US11024808B2 (en) 2015-12-29 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US11038115B2 (en) 2017-05-18 2021-06-15 Universal Display Corporation Organic electroluminescent materials and device
US11038117B2 (en) 2017-04-11 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US11038137B2 (en) 2017-04-28 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US11050028B2 (en) 2017-01-24 2021-06-29 Universal Display Corporation Organic electroluminescent materials and devices
US11056657B2 (en) 2015-02-27 2021-07-06 University Display Corporation Organic electroluminescent materials and devices
US11056658B2 (en) 2017-03-29 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US11053268B2 (en) 2017-01-20 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US11081647B2 (en) 2016-04-22 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11081659B2 (en) 2018-01-10 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11081658B2 (en) 2016-10-03 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11084838B2 (en) 2017-04-21 2021-08-10 Universal Display Corporation Organic electroluminescent materials and device
US11094891B2 (en) 2016-03-16 2021-08-17 Universal Display Corporation Organic electroluminescent materials and devices
US11101434B2 (en) 2017-04-21 2021-08-24 Universal Display Corporation Organic electroluminescent materials and devices
US11108000B2 (en) 2014-08-07 2021-08-31 Unniversal Display Corporation Organic electroluminescent materials and devices
US11117897B2 (en) 2017-05-01 2021-09-14 Universal Display Corporation Organic electroluminescent materials and devices
US11127906B2 (en) 2016-10-03 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11127905B2 (en) 2015-07-29 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11139443B2 (en) 2017-03-31 2021-10-05 Universal Display Corporation Organic electroluminescent materials and devices
US11142538B2 (en) 2018-03-12 2021-10-12 Universal Display Corporation Organic electroluminescent materials and devices
US11152579B2 (en) 2016-12-28 2021-10-19 Universal Display Corporation Organic electroluminescent materials and devices
US11158820B2 (en) 2017-03-29 2021-10-26 Universal Display Corporation Organic electroluminescent materials and devices
US11165028B2 (en) 2018-03-12 2021-11-02 Universal Display Corporation Organic electroluminescent materials and devices
US11168103B2 (en) 2017-11-17 2021-11-09 Universal Display Corporation Organic electroluminescent materials and devices
US11174259B2 (en) 2017-06-23 2021-11-16 Universal Display Corporation Organic electroluminescent materials and devices
US11180519B2 (en) 2018-02-09 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11183642B2 (en) 2016-10-03 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11183646B2 (en) 2017-11-07 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11189804B2 (en) 2016-10-03 2021-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US11196010B2 (en) 2016-10-03 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US11201299B2 (en) 2017-05-04 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US11201298B2 (en) 2017-01-09 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US11214587B2 (en) 2017-11-07 2022-01-04 Universal Display Corporation Organic electroluminescent materials and devices
US11217757B2 (en) 2018-03-12 2022-01-04 Universal Display Corporation Host materials for electroluminescent devices
US11228002B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11228004B2 (en) 2018-06-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11228010B2 (en) 2017-07-26 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11228003B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11233203B2 (en) 2018-09-06 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11233204B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11233205B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11239433B2 (en) 2017-07-26 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11239434B2 (en) 2018-02-09 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11239432B2 (en) 2016-10-14 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11261207B2 (en) 2018-06-25 2022-03-01 Universal Display Corporation Organic electroluminescent materials and devices
US11271177B2 (en) 2018-01-11 2022-03-08 Universal Display Corporation Organic electroluminescent materials and devices
US11276829B2 (en) 2017-03-31 2022-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US11279722B2 (en) 2018-03-12 2022-03-22 Universal Display Corporation Organic electroluminescent materials and devices
US11296283B2 (en) 2018-06-04 2022-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US11302872B2 (en) 2015-09-09 2022-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US11322691B2 (en) 2017-07-26 2022-05-03 Universal Display Corporation Organic electroluminescent materials and devices
US11325932B2 (en) 2019-02-08 2022-05-10 Universal Display Corporation Organic electroluminescent materials and devices
US11342509B2 (en) 2018-02-09 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11339182B2 (en) 2018-06-07 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11342513B2 (en) 2018-05-04 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11349083B2 (en) 2017-08-10 2022-05-31 Universal Display Corporation Organic electroluminescent materials and devices
US11367840B2 (en) 2018-01-26 2022-06-21 Universal Display Corporation Organic electroluminescent materials and devices
US11374181B2 (en) 2019-08-14 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11370809B2 (en) 2019-02-08 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11390639B2 (en) 2018-04-13 2022-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US11424420B2 (en) 2017-09-07 2022-08-23 Universal Display Corporation Organic electroluminescent materials and devices
US11437591B2 (en) 2017-08-24 2022-09-06 Universal Display Corporation Organic electroluminescent materials and devices
US11444249B2 (en) 2017-09-07 2022-09-13 Universal Display Corporation Organic electroluminescent materials and devices
US11450822B2 (en) 2018-05-25 2022-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US11459349B2 (en) 2018-05-25 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US11462697B2 (en) 2017-08-22 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US11469384B2 (en) 2018-11-02 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11469383B2 (en) 2018-10-08 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11469382B2 (en) 2017-07-12 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11476430B2 (en) 2018-10-15 2022-10-18 Universal Display Corporation Organic electroluminescent materials and devices
US11482683B2 (en) 2016-06-20 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US11485706B2 (en) 2018-09-11 2022-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US11495752B2 (en) 2018-10-08 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11495757B2 (en) 2017-06-23 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11495756B2 (en) 2019-05-07 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11508913B2 (en) 2017-08-10 2022-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US11512093B2 (en) 2019-03-04 2022-11-29 Universal Display Corporation Compound used for organic light emitting device (OLED), consumer product and formulation
US11515494B2 (en) 2018-05-04 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11515489B2 (en) 2018-11-28 2022-11-29 Universal Display Corporation Host materials for electroluminescent devices
US11515493B2 (en) 2018-01-11 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11515482B2 (en) 2018-10-23 2022-11-29 Universal Display Corporation Deep HOMO (highest occupied molecular orbital) emitter device structures
US11522140B2 (en) 2015-08-17 2022-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US11542289B2 (en) 2018-01-26 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11545637B2 (en) 2017-01-13 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11545636B2 (en) 2016-12-15 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11552261B2 (en) 2017-06-23 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US11548905B2 (en) 2016-12-15 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US11555048B2 (en) 2016-12-01 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11557738B2 (en) 2019-02-22 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11557733B2 (en) 2018-03-12 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11569480B2 (en) 2019-03-12 2023-01-31 Universal Display Corporation Plasmonic OLEDs and vertical dipole emitters
US11600787B2 (en) 2019-08-30 2023-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US11605791B2 (en) 2017-09-01 2023-03-14 Universal Display Corporation Organic electroluminescent materials and devices
US11608321B2 (en) 2017-06-23 2023-03-21 Universal Display Corporation Organic electroluminescent materials and devices
US11616203B2 (en) 2018-04-17 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US11613550B2 (en) 2019-04-30 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes
US11623936B2 (en) 2018-12-11 2023-04-11 Universal Display Corporation Organic electroluminescent materials and devices
US11634445B2 (en) 2019-05-21 2023-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US11637261B2 (en) 2019-03-12 2023-04-25 Universal Display Corporation Nanopatch antenna outcoupling structure for use in OLEDs
US11639363B2 (en) 2019-04-22 2023-05-02 Universal Display Corporation Organic electroluminescent materials and devices
US11647667B2 (en) 2019-06-14 2023-05-09 Universal Display Corporation Organic electroluminescent compounds and organic light emitting devices using the same
US11672176B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Host materials for electroluminescent devices
US11672165B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US11678565B2 (en) 2017-06-23 2023-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US11690285B2 (en) 2018-11-28 2023-06-27 Universal Display Corporation Electroluminescent devices
US11685754B2 (en) 2019-07-22 2023-06-27 Universal Display Corporation Heteroleptic organic electroluminescent materials
US11696492B2 (en) 2017-09-07 2023-07-04 Universal Display Corporation Organic electroluminescent materials and devices
US11700765B2 (en) 2018-01-10 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11697653B2 (en) 2019-10-21 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11706972B2 (en) 2015-09-08 2023-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US11708355B2 (en) 2019-08-01 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11716899B2 (en) 2018-11-28 2023-08-01 Universal Display Corporation Organic electroluminescent materials and devices
US11716900B2 (en) 2018-05-30 2023-08-01 Universal Display Corporation Host materials for electroluminescent devices
US11723269B2 (en) 2017-08-22 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11718634B2 (en) 2018-09-14 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11725022B2 (en) 2017-06-23 2023-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US11737349B2 (en) 2018-12-12 2023-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US11739081B2 (en) 2019-03-11 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11744141B2 (en) 2017-08-09 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11744142B2 (en) 2017-08-10 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11758804B2 (en) 2017-06-23 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11753427B2 (en) 2018-05-04 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11753425B2 (en) 2018-07-11 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11765968B2 (en) 2017-01-23 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11765965B2 (en) 2019-10-30 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11765970B2 (en) 2017-07-26 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11773320B2 (en) 2019-02-21 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11778897B2 (en) 2017-09-20 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11778895B2 (en) 2020-01-13 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11780829B2 (en) 2019-01-30 2023-10-10 The University Of Southern California Organic electroluminescent materials and devices
US11780865B2 (en) 2017-01-09 2023-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US11793073B2 (en) 2018-05-06 2023-10-17 Universal Display Corporation Host materials for electroluminescent devices
US11802136B2 (en) 2017-06-23 2023-10-31 Universal Display Corporation Organic electroluminescent materials and devices
EP4271160A2 (en) 2015-02-13 2023-11-01 Merck Patent GmbH Aromatic heterocyclic derivative, and organic electroluminescent element, illumination device, and display device using aromatic heterocyclic derivative
US11812624B2 (en) 2019-01-30 2023-11-07 The University Of Southern California Organic electroluminescent materials and devices
US11812622B2 (en) 2015-09-25 2023-11-07 Universal Display Corporation Organic electroluminescent compounds and devices
US11814403B2 (en) 2017-06-23 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11825735B2 (en) 2017-11-28 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11820783B2 (en) 2019-09-06 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11825736B2 (en) 2018-11-19 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11827651B2 (en) 2019-05-13 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US11832510B2 (en) 2017-06-23 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices
US11844266B2 (en) 2019-01-31 2023-12-12 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
US11845764B2 (en) 2018-01-26 2023-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US11864458B2 (en) 2019-10-08 2024-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US11871653B2 (en) 2019-02-22 2024-01-09 Universal Display Corporation Organic electroluminescent materials and devices
US11882759B2 (en) 2018-04-13 2024-01-23 Universal Display Corporation Organic electroluminescent materials and devices
US11889708B2 (en) 2019-11-14 2024-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US11903305B2 (en) 2018-09-24 2024-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US11910702B2 (en) 2017-11-07 2024-02-20 Universal Display Corporation Organic electroluminescent devices
US11910700B2 (en) 2009-03-23 2024-02-20 Universal Display Corporation Heteroleptic iridium complexes as dopants
US11910699B2 (en) 2017-08-10 2024-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US11917900B2 (en) 2020-01-28 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11917843B2 (en) 2017-07-26 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11919914B2 (en) 2019-10-25 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11920070B2 (en) 2019-07-12 2024-03-05 The University Of Southern California Luminescent janus-type, two-coordinated metal complexes
US11925103B2 (en) 2018-06-05 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11925105B2 (en) 2019-08-26 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11925102B2 (en) 2015-06-04 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11926638B2 (en) 2019-07-22 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US11930699B2 (en) 2019-08-15 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US11932660B2 (en) 2020-01-29 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11937494B2 (en) 2019-08-28 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11937503B2 (en) 2017-11-30 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11944000B2 (en) 2013-10-29 2024-03-26 Universal Display Corporation Organic electroluminescent materials and devices
US11950493B2 (en) 2019-10-15 2024-04-02 Universal Display Corporation Organic electroluminescent materials and devices
US11957047B2 (en) 2022-08-15 2024-04-09 Universal Display Corporation Organic electroluminescent materials and devices

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001247859A (en) * 1999-12-27 2001-09-14 Fuji Photo Film Co Ltd Luminescent element material comprising ortho metallized iridium complex, luminescent element and novel iridium complex
JP2002105055A (en) * 2000-09-29 2002-04-10 Fuji Photo Film Co Ltd Method for manufacturing indium complex or its tautomer
WO2004101707A1 (en) * 2003-05-16 2004-11-25 Isis Innovation Limited Organic phosphorescent material and organic optoelectronic device
WO2005007767A2 (en) * 2003-07-22 2005-01-27 Idemitsu Kosan Co Metal complex compound and organic electroluminescent device using same
JP2005053912A (en) * 2003-08-07 2005-03-03 Samsung Sdi Co Ltd Iridium compound and organic electroluminescent element given by adopting the same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001052867A (en) * 1999-08-05 2001-02-23 Toyota Motor Corp Organic el element and its manufacture
JP2001160488A (en) * 1999-12-01 2001-06-12 Konica Corp Organic electroluminescent element
JPWO2004034751A1 (en) * 2002-10-09 2006-02-09 出光興産株式会社 Organic electroluminescence device

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001247859A (en) * 1999-12-27 2001-09-14 Fuji Photo Film Co Ltd Luminescent element material comprising ortho metallized iridium complex, luminescent element and novel iridium complex
JP2002105055A (en) * 2000-09-29 2002-04-10 Fuji Photo Film Co Ltd Method for manufacturing indium complex or its tautomer
WO2004101707A1 (en) * 2003-05-16 2004-11-25 Isis Innovation Limited Organic phosphorescent material and organic optoelectronic device
WO2005007767A2 (en) * 2003-07-22 2005-01-27 Idemitsu Kosan Co Metal complex compound and organic electroluminescent device using same
JP2005053912A (en) * 2003-08-07 2005-03-03 Samsung Sdi Co Ltd Iridium compound and organic electroluminescent element given by adopting the same

Cited By (750)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9871219B2 (en) 2005-04-13 2018-01-16 Universal Display Corporation Organic light emitting devices
US9647227B2 (en) 2005-04-13 2017-05-09 Universal Display Corporation Organic light emitting devices
US9735377B2 (en) 2005-05-06 2017-08-15 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
US8133597B2 (en) 2005-09-06 2012-03-13 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
WO2007029466A1 (en) * 2005-09-06 2007-03-15 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
WO2007052431A1 (en) * 2005-10-31 2007-05-10 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
JP4893627B2 (en) * 2005-10-31 2012-03-07 コニカミノルタホールディングス株式会社 Organic electroluminescence element, display device and lighting device
US8758903B2 (en) 2005-10-31 2014-06-24 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and lighting device
JP2007189001A (en) * 2006-01-12 2007-07-26 Konica Minolta Holdings Inc Organic electroluminescence element, material thereof, display device, and luminaire
JP2007204592A (en) * 2006-02-01 2007-08-16 Showa Denko Kk Polymer light-emitting material, organic electroluminescent element and display
US10978649B2 (en) 2006-02-10 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US9893306B2 (en) 2006-02-10 2018-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US9065063B2 (en) 2006-02-10 2015-06-23 Universal Display Corporation Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
US8889864B2 (en) 2006-02-10 2014-11-18 Universal Display Corporation Metal complexes of cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands and isoelectronic and benzannulated analogs thereof
US10158090B2 (en) 2006-02-10 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
US10403831B2 (en) 2006-02-10 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10749121B2 (en) 2006-02-10 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US9548462B2 (en) 2006-02-10 2017-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US9281483B2 (en) 2006-02-10 2016-03-08 Universal Display Corporation Organic electroluminescent materials and devices
EP1988143A4 (en) * 2006-02-20 2009-11-25 Konica Minolta Holdings Inc Organic electroluminescence element, white light emitting element, display device and illuminating device
JP5520479B2 (en) * 2006-02-20 2014-06-11 コニカミノルタ株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT, WHITE LIGHT EMITTING ELEMENT, AND LIGHTING DEVICE
US8778506B2 (en) 2006-02-20 2014-07-15 Konica Minolta Holdings, Inc. Organic electroluminescent element, white light emission element, full color display device and lighting device
JP2012256910A (en) * 2006-02-20 2012-12-27 Konica Minolta Holdings Inc Organic electroluminescent element, white light-emitting element, display device, and lighting device
EP1988144A4 (en) * 2006-02-20 2010-07-21 Konica Minolta Holdings Inc Organic electroluminescence element material, organic electroluminescence element, display device and illuminating device
JP5104751B2 (en) * 2006-02-20 2012-12-19 コニカミノルタホールディングス株式会社 Organic electroluminescence element material
WO2007097153A1 (en) * 2006-02-20 2007-08-30 Konica Minolta Holdings, Inc. Organic electroluminescence element material, organic electroluminescence element, display device and illuminating device
JPWO2007097153A1 (en) * 2006-02-20 2009-07-09 コニカミノルタホールディングス株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
JPWO2007097149A1 (en) * 2006-02-20 2009-07-09 コニカミノルタホールディングス株式会社 ORGANIC ELECTROLUMINESCENCE ELEMENT, WHITE LIGHT EMITTING ELEMENT, DISPLAY DEVICE, AND LIGHTING DEVICE
JP2012207231A (en) * 2006-02-20 2012-10-25 Konica Minolta Holdings Inc Organic electroluminescent element material
WO2007097149A1 (en) * 2006-02-20 2007-08-30 Konica Minolta Holdings, Inc. Organic electroluminescence element, white light emitting element, display device and illuminating device
JPWO2007108362A1 (en) * 2006-03-17 2009-08-06 コニカミノルタホールディングス株式会社 Organic electroluminescence element, display device and lighting device
EP1998387A1 (en) 2006-03-17 2008-12-03 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
JP5672648B2 (en) * 2006-03-17 2015-02-18 コニカミノルタ株式会社 Organic electroluminescence element, display device and lighting device
JP2013138220A (en) * 2006-03-17 2013-07-11 Konica Minolta Inc Organic electroluminescent element, display device, and lighting device
EP1998387A4 (en) * 2006-03-17 2011-06-15 Konica Minolta Holdings Inc Organic electroluminescent device, display and illuminating device
US9692000B2 (en) 2006-03-23 2017-06-27 Konica Minolta, Inc. Organic electroluminescent element, display device and illuminating device
JP2012231147A (en) * 2006-03-23 2012-11-22 Konica Minolta Holdings Inc Organic electroluminescent element, display device and illuminating device
US8920942B2 (en) 2006-03-23 2014-12-30 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and illuminating device
JP2012199575A (en) * 2006-03-23 2012-10-18 Konica Minolta Holdings Inc Organic electroluminescent element, display device, and luminaire
US9634275B2 (en) 2006-03-23 2017-04-25 Konica Minolta, Inc. Organic electroluminescent element, display device and illuminating device
EP1998388A1 (en) 2006-03-23 2008-12-03 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
EP3081619A1 (en) * 2006-03-23 2016-10-19 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and illuminating device
US9634276B2 (en) 2006-03-23 2017-04-25 Konica Minolta, Inc. Organic electroluminescent element, display device and illuminating device
EP2615153A1 (en) * 2006-03-23 2013-07-17 Konica Minolta Holdings, Inc. Organic electroluminescent device, display and illuminating device
EP1998388A4 (en) * 2006-03-23 2012-02-08 Konica Minolta Holdings Inc Organic electroluminescent device, display and illuminating device
JPWO2008035664A1 (en) * 2006-09-20 2010-01-28 コニカミノルタホールディングス株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
JP5556014B2 (en) * 2006-09-20 2014-07-23 コニカミノルタ株式会社 Organic electroluminescence device
JP5644050B2 (en) * 2006-09-20 2014-12-24 コニカミノルタ株式会社 Organic electroluminescence element material
JPWO2008035571A1 (en) * 2006-09-20 2010-01-28 コニカミノルタホールディングス株式会社 Organic electroluminescence device
JP2008101114A (en) * 2006-10-19 2008-05-01 Konica Minolta Holdings Inc Organic electroluminescent element material, organic electroluminescent element, display and illuminating device
US9899612B2 (en) 2006-12-08 2018-02-20 Universal Display Corporation Organic electroluminescent materials and devices
WO2008072539A1 (en) * 2006-12-11 2008-06-19 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
US8866377B2 (en) 2006-12-28 2014-10-21 Universal Display Corporation Long lifetime phosphorescent organic light emitting device (OLED) structures
US9911930B2 (en) 2007-03-08 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US10230060B2 (en) 2007-03-08 2019-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US9577201B2 (en) 2007-03-08 2017-02-21 Universal Display Corporation Organic electroluminescent materials and devices
US9142786B2 (en) 2007-03-08 2015-09-22 Universal Display Corporation Phosphorescent materials
US9853227B2 (en) 2007-03-08 2017-12-26 Universal Display Corporation Organic electroluminescent materials and devices
US11495755B2 (en) 2007-03-08 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US9190621B2 (en) 2007-03-08 2015-11-17 Universal Display Corporation Materials for organic light emitting diode
US10600975B2 (en) 2007-03-08 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US9590180B2 (en) 2007-06-23 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US8822708B2 (en) 2007-08-08 2014-09-02 Universal Display Corporation Benzo-fused thiophene / triphenylene hybrid materials
US10312450B2 (en) 2007-08-08 2019-06-04 Universal Display Corporation Organic electroluminescent materials and devices
US11690286B2 (en) 2007-08-08 2023-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US9577200B2 (en) 2007-08-08 2017-02-21 Universal Display Corporation Organic electroluminescent materials and devices
US10957858B2 (en) 2007-08-08 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US9997727B2 (en) 2007-08-08 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US9153786B2 (en) 2007-08-08 2015-10-06 Universal Display Corporation Organic electroluminescent materials and devices
US10374171B2 (en) 2007-08-08 2019-08-06 Universal Display Corporation Organic electroluminescent materials and devices
US9608206B2 (en) 2007-08-08 2017-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US8384068B2 (en) 2007-10-02 2013-02-26 Basf Se Use of acridine derivatives as matrix materials and/or electron blockers in OLEDs
US8586204B2 (en) 2007-12-28 2013-11-19 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
US8221905B2 (en) 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
US9997726B2 (en) 2007-12-28 2018-06-12 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US9123903B2 (en) 2007-12-28 2015-09-01 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8007927B2 (en) 2007-12-28 2011-08-30 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8580402B2 (en) 2007-12-28 2013-11-12 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
US8040053B2 (en) 2008-02-09 2011-10-18 Universal Display Corporation Organic light emitting device architecture for reducing the number of organic materials
US8592586B2 (en) 2008-06-10 2013-11-26 Basf Se Transition metal complexes and use thereof in organic light-emitting diodes V
US8377332B2 (en) 2008-06-10 2013-02-19 Basf Se Transition metal complexes and use thereof in organic light emitting diodes—III
US8410270B2 (en) 2008-06-10 2013-04-02 Basf Se Transition metal complexes and use thereof in organic light-emitting diodes V
US8859110B2 (en) 2008-06-20 2014-10-14 Basf Se Cyclic phosphazene compounds and use thereof in organic light emitting diodes
US8440326B2 (en) 2008-06-30 2013-05-14 Universal Display Corporation Hole transport materials containing triphenylene
US11482685B2 (en) 2008-09-03 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US10593896B2 (en) 2008-09-03 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US10892426B2 (en) 2008-09-03 2021-01-12 Universal Display Corporation Organic electroluminescent materials and devices
US9630983B2 (en) 2008-09-03 2017-04-25 Universal Display Corporation Organic electroluminescent material and devices
US9076973B2 (en) 2008-09-03 2015-07-07 Universal Display Corporation Phosphorescent materials
US10186672B2 (en) 2008-09-03 2019-01-22 Universal Display Corporation Organic electroluminescent materials and devices
US8519384B2 (en) 2008-09-03 2013-08-27 Universal Display Corporation Phosphorescent materials
US8513658B2 (en) 2008-09-04 2013-08-20 Universal Display Corporation White phosphorescent organic light emitting devices
US10084143B2 (en) 2008-09-16 2018-09-25 Universal Display Corporation Phosphorescent materials
US9034483B2 (en) 2008-09-16 2015-05-19 Universal Display Corporation Phosphorescent materials
US9455411B2 (en) 2008-09-25 2016-09-27 Universal Display Corporation Organic electroluminescent materials and devices
US8053770B2 (en) 2008-10-14 2011-11-08 Universal Display Corporation Emissive layer patterning for OLED
US8367223B2 (en) 2008-11-11 2013-02-05 Universal Display Corporation Heteroleptic phosphorescent emitters
US10008678B2 (en) 2008-12-12 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US8778511B2 (en) 2008-12-12 2014-07-15 Universal Display Corporation OLED stability via doped hole transport layer
US8815415B2 (en) 2008-12-12 2014-08-26 Universal Display Corporation Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes
US8952363B2 (en) 2009-01-16 2015-02-10 Universal Display Corporation Organic electroluminescent materials and devices
US9067947B2 (en) 2009-01-16 2015-06-30 Universal Display Corporation Organic electroluminescent materials and devices
US9831442B2 (en) 2009-01-16 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9518063B2 (en) 2009-01-16 2016-12-13 Universal Display Corporation Organic electroluminescent materials and devices
US9184397B2 (en) 2009-03-23 2015-11-10 Universal Display Corporation Heteroleptic iridium complexes as dopants
US11910700B2 (en) 2009-03-23 2024-02-20 Universal Display Corporation Heteroleptic iridium complexes as dopants
US8722205B2 (en) 2009-03-23 2014-05-13 Universal Display Corporation Heteroleptic iridium complex
US11380854B2 (en) 2009-03-23 2022-07-05 Universal Display Corporation Heteroleptic iridium complexes as dopants
US11637251B2 (en) 2009-03-23 2023-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US10312458B2 (en) 2009-03-23 2019-06-04 Universal Display Corporation Organic electroluminescent materials and devices
US10056566B2 (en) 2009-03-23 2018-08-21 Universal Display Corporation Organic electroluminescent materials and devices
US11910701B2 (en) 2009-03-23 2024-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US9359549B2 (en) 2009-04-06 2016-06-07 Universal Display Corporation Organic electroluminescent materials and devices
US10374173B2 (en) 2009-04-28 2019-08-06 Universal Display Corporation Organic electroluminescent materials and devices
US8557400B2 (en) 2009-04-28 2013-10-15 Universal Display Corporation Iridium complex with methyl-D3 substitution
US9634265B2 (en) 2009-04-28 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US9005771B2 (en) 2009-05-12 2015-04-14 Universal Display Corporation 2-azatriphenylene materials for organic light emitting diodes
US9673406B2 (en) 2009-05-20 2017-06-06 Universal Display Corporation Metal complexes with boron-nitrogen heterocycle containing ligands
US8545996B2 (en) 2009-11-02 2013-10-01 The University Of Southern California Ion-pairing soft salts based on organometallic complexes and their applications in organic light emitting diodes
US9773986B2 (en) 2009-11-19 2017-09-26 The University Of Southern California Copper(I)-carbene complexes and organic electroluminescent devices
CN102648205B (en) * 2009-12-08 2015-11-25 佳能株式会社 Iridium complex and the organic luminescent device comprising this compound
CN102648205A (en) * 2009-12-08 2012-08-22 佳能株式会社 Novel iridium complex and organic light-emitting device including the same
US8980444B2 (en) 2009-12-08 2015-03-17 Canon Kabushiki Kaisha Iridium complex and organic light-emitting device including the same
US9054344B2 (en) 2010-01-20 2015-06-09 Universal Display Corporation Electroluminescent devices for lighting applications
US9156870B2 (en) 2010-02-25 2015-10-13 Universal Display Corporation Phosphorescent emitters
US9175211B2 (en) 2010-03-03 2015-11-03 Universal Display Corporation Phosphorescent materials
US8963132B2 (en) 2010-03-25 2015-02-24 Universal Display Corporation Solution processable doped triarylamine hole injection materials
US9040962B2 (en) 2010-04-28 2015-05-26 Universal Display Corporation Depositing premixed materials
US8968887B2 (en) 2010-04-28 2015-03-03 Universal Display Corporation Triphenylene-benzofuran/benzothiophene/benzoselenophene compounds with substituents joining to form fused rings
US9543532B2 (en) 2010-06-11 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US8742657B2 (en) 2010-06-11 2014-06-03 Universal Display Corporation Triplet-Triplet annihilation up conversion (TTA-UC) for display and lighting applications
US9140428B2 (en) 2010-06-11 2015-09-22 Universal Display Corporation Triplet-triplet annihilation up-conversation for display and lighting applications
US9435021B2 (en) 2010-07-29 2016-09-06 University Of Southern California Co-deposition methods for the fabrication of organic optoelectronic devices
US11316113B2 (en) 2010-08-20 2022-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US11289659B2 (en) 2010-08-20 2022-03-29 Universal Display Corporation Organic electroluminescent materials and devices
US9954180B2 (en) 2010-08-20 2018-04-24 Universal Display Corporation Bicarbazole compounds for OLEDs
US8932734B2 (en) 2010-10-08 2015-01-13 Universal Display Corporation Organic electroluminescent materials and devices
US9401482B2 (en) 2010-10-08 2016-07-26 Universal Display Corporation Organic electroluminescent materials and devices
JP2018150309A (en) * 2010-11-26 2018-09-27 株式会社半導体エネルギー研究所 Compound
JP2013040159A (en) * 2010-11-26 2013-02-28 Semiconductor Energy Lab Co Ltd Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
KR101893624B1 (en) * 2010-11-26 2018-08-30 가부시키가이샤 한도오따이 에네루기 켄큐쇼 Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
CN103347886A (en) * 2010-11-26 2013-10-09 株式会社半导体能源研究所 Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
JP2016186082A (en) * 2010-11-26 2016-10-27 株式会社半導体エネルギー研究所 Light-emitting material, light-emitting element, light-emitting device, electronic device, and lighting device
WO2012070596A1 (en) * 2010-11-26 2012-05-31 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
KR20130143700A (en) * 2010-11-26 2013-12-31 가부시키가이샤 한도오따이 에네루기 켄큐쇼 Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
US10147892B2 (en) 2010-12-07 2018-12-04 The University Of Southern California Organic electroluminescent materials and devices
US11374180B2 (en) 2011-01-13 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US10008677B2 (en) 2011-01-13 2018-06-26 Universal Display Corporation Materials for organic light emitting diode
US10680189B2 (en) 2011-01-13 2020-06-09 Universal Display Corporation Materials for organic light emitting diodes
US9130177B2 (en) 2011-01-13 2015-09-08 Universal Display Corporation 5-substituted 2 phenylquinoline complexes materials for light emitting diode
US8754232B2 (en) 2011-02-23 2014-06-17 Universal Display Corporation Methods of making bis-tridentate carbene complexes of ruthenium and osmium
US10388890B2 (en) 2011-02-23 2019-08-20 Universal Display Corporation Organic electroluminescent heterocyclic carbene metal complexes and devices containing the same
US8871361B2 (en) 2011-02-23 2014-10-28 Universal Display Corporation Tetradentate platinum complexes
US8563737B2 (en) 2011-02-23 2013-10-22 Universal Display Corporation Methods of making bis-tridentate carbene complexes of ruthenium and osmium
US8748011B2 (en) 2011-02-23 2014-06-10 Universal Display Corporation Ruthenium carbene complexes for OLED material
US10381580B2 (en) 2011-02-23 2019-08-13 Universal Display Corporation Organic electroluminescent materials and devices
US9005772B2 (en) 2011-02-23 2015-04-14 Universal Display Corporation Thioazole and oxazole carbene metal complexes as phosphorescent OLED materials
US9947880B2 (en) 2011-02-23 2018-04-17 Universal Display Corporation Organic electroluminescent materials and devices
US8492006B2 (en) 2011-02-24 2013-07-23 Universal Display Corporation Germanium-containing red emitter materials for organic light emitting diode
US9972793B2 (en) 2011-03-08 2018-05-15 Universal Display Corporation Organic electroluminescent materials and devices
US11600791B2 (en) 2011-03-08 2023-03-07 Universal Display Corporation Organic electroluminescent materials and devices
JP2012188357A (en) * 2011-03-08 2012-10-04 Nagasaki Univ Metal complex, light-emitting device, and display device
US10873038B2 (en) 2011-03-08 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US8883322B2 (en) 2011-03-08 2014-11-11 Universal Display Corporation Pyridyl carbene phosphorescent emitters
WO2012124622A1 (en) 2011-03-14 2012-09-20 東レ株式会社 Light-emitting element material and light-emitting element
US9397312B2 (en) 2011-05-11 2016-07-19 Universal Display Corporation Process for fabricating metal bus lines for OLED lighting panels
US8927308B2 (en) 2011-05-12 2015-01-06 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
US9450027B2 (en) 2011-05-12 2016-09-20 Universal Display Corporation Method of forming bus line designs for large-area OLED lighting
WO2012153725A1 (en) 2011-05-12 2012-11-15 東レ株式会社 Light-emitting element material and light-emitting element
US9212197B2 (en) 2011-05-19 2015-12-15 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants
US8795850B2 (en) 2011-05-19 2014-08-05 Universal Display Corporation Phosphorescent heteroleptic phenylbenzimidazole dopants and new synthetic methodology
US9257658B2 (en) 2011-05-19 2016-02-09 Universal Display Corporation Method of making organic electroluminescent materials
US8748012B2 (en) 2011-05-25 2014-06-10 Universal Display Corporation Host materials for OLED
DE112012002237B4 (en) 2011-05-25 2022-12-22 Universal Display Corporation Host Materials for OLEDS
US10158089B2 (en) 2011-05-27 2018-12-18 Universal Display Corporation Organic electroluminescent materials and devices
US11189805B2 (en) 2011-05-27 2021-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US10079349B2 (en) 2011-05-27 2018-09-18 Universal Display Corporation Organic electroluminescent materials and devices
JP2016196518A (en) * 2011-06-03 2016-11-24 株式会社半導体エネルギー研究所 Organometallic complex
US9406894B2 (en) 2011-06-03 2016-08-02 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, organic light-emitting element, light-emitting device, electronic device, and lighting device
JP2013010752A (en) * 2011-06-03 2013-01-17 Semiconductor Energy Lab Co Ltd Organometallic complex, organic light-emitting element, light-emitting device, electronic equipment and lighting system
US9812656B2 (en) 2011-06-08 2017-11-07 Universal Display Corporation Organic electroluminescent materials and devices
US10978648B2 (en) 2011-06-08 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US9847495B2 (en) 2011-06-08 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US9755164B2 (en) 2011-06-08 2017-09-05 Universal Display Corporation Organic electroluminescent materials and devices
US10297769B2 (en) 2011-06-08 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US11063229B2 (en) 2011-06-08 2021-07-13 Universal Display Corporation Organic electroluminescent materials and devices
US10340313B2 (en) 2011-06-17 2019-07-02 Universal Display Corporation Non-common capping layer on an organic device
US8884316B2 (en) 2011-06-17 2014-11-11 Universal Display Corporation Non-common capping layer on an organic device
US9054343B2 (en) 2011-06-17 2015-06-09 Universal Display Corporation Fine tuning of emission spectra by combination of multiple emitter spectra
US8659036B2 (en) 2011-06-17 2014-02-25 Universal Display Corporation Fine tuning of emission spectra by combination of multiple emitter spectra
US11751455B2 (en) 2011-06-17 2023-09-05 Universal Display Corporation Non-common capping layer on an organic device
US9647221B2 (en) 2011-07-14 2017-05-09 Universal Display Corporation Organic light-emitting devices
US9397310B2 (en) 2011-07-14 2016-07-19 Universal Display Corporation Organice electroluminescent materials and devices
US9252377B2 (en) 2011-07-14 2016-02-02 Universal Display Corporation Inorganic hosts in OLEDs
US10214551B2 (en) 2011-07-25 2019-02-26 Universal Display Corporation Organic electroluminescent materials and devices
US9783564B2 (en) 2011-07-25 2017-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US8709615B2 (en) 2011-07-28 2014-04-29 Universal Display Corporation Heteroleptic iridium complexes as dopants
US9313857B2 (en) 2011-08-04 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US8926119B2 (en) 2011-08-04 2015-01-06 Universal Display Corporation Extendable light source with variable light emitting area
US9493698B2 (en) 2011-08-31 2016-11-15 Universal Display Corporation Organic electroluminescent materials and devices
US9142788B2 (en) 2011-11-14 2015-09-22 Universal Display Corporation Host materials for OLEDs
US8652656B2 (en) 2011-11-14 2014-02-18 Universal Display Corporation Triphenylene silane hosts
US9193745B2 (en) 2011-11-15 2015-11-24 Universal Display Corporation Heteroleptic iridium complex
US9217004B2 (en) 2011-11-21 2015-12-22 Universal Display Corporation Organic light emitting materials
US9512355B2 (en) 2011-12-09 2016-12-06 Universal Display Corporation Organic light emitting materials
US10454046B2 (en) 2011-12-09 2019-10-22 Universal Display Corporation Organic electroluminescent materials and devices
US11482684B2 (en) 2011-12-09 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US9455417B2 (en) 2011-12-13 2016-09-27 Universal Display Corporation Split electrode for organic devices
US9461254B2 (en) 2012-01-03 2016-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US8987451B2 (en) 2012-01-03 2015-03-24 Universal Display Corporation Synthesis of cyclometallated platinum(II) complexes
US9163174B2 (en) 2012-01-04 2015-10-20 Universal Display Corporation Highly efficient phosphorescent materials
DE102013200085B4 (en) 2012-01-06 2020-06-18 Universal Display Corporation Highly efficient phosphorescent materials
US9447113B2 (en) 2012-01-10 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US8969592B2 (en) 2012-01-10 2015-03-03 Universal Display Corporation Heterocyclic host materials
US10211413B2 (en) 2012-01-17 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
EP2623508A1 (en) 2012-02-02 2013-08-07 Konica Minolta Advanced Layers, Inc. Iridium complex compound, organic electroluminescent element material, organic electroluminescent element, illumination device and display device
US9118017B2 (en) 2012-02-27 2015-08-25 Universal Display Corporation Host compounds for red phosphorescent OLEDs
US9386657B2 (en) 2012-03-15 2016-07-05 Universal Display Corporation Organic Electroluminescent materials and devices
DE102013003605B4 (en) 2012-03-15 2023-08-17 Universal Display Corporation Secondary hole transport layer with tricarbazole compounds
US9548459B2 (en) 2012-03-15 2017-01-17 Universal Display Corporation Organic materials for organic light emitting devices
US9054323B2 (en) 2012-03-15 2015-06-09 Universal Display Corporation Secondary hole transporting layer with diarylamino-phenyl-carbazole compounds
US9184399B2 (en) 2012-05-04 2015-11-10 Universal Display Corporation Asymmetric hosts with triaryl silane side chains
US9773985B2 (en) 2012-05-21 2017-09-26 Universal Display Corporation Organic electroluminescent materials and devices
US9670404B2 (en) 2012-06-06 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9502672B2 (en) 2012-06-21 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US9725476B2 (en) 2012-07-09 2017-08-08 Universal Display Corporation Silylated metal complexes
US9231218B2 (en) 2012-07-10 2016-01-05 Universal Display Corporation Phosphorescent emitters containing dibenzo[1,4]azaborinine structure
US9540329B2 (en) 2012-07-19 2017-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US9059412B2 (en) 2012-07-19 2015-06-16 Universal Display Corporation Transition metal complexes containing substituted imidazole carbene as ligands and their application in OLEDs
DE102013214144B4 (en) 2012-07-19 2023-02-16 Universal Display Corp. Diarylamino-substituted metal complexes
WO2014017484A1 (en) 2012-07-25 2014-01-30 東レ株式会社 Light emitting element material and light emitting element
US9663544B2 (en) 2012-07-25 2017-05-30 Universal Display Corporation Organic electroluminescent materials and devices
US9627631B2 (en) 2012-07-30 2017-04-18 Universal Display Corporation Organic electroluminescent materials and devices
US9318710B2 (en) 2012-07-30 2016-04-19 Universal Display Corporation Organic electroluminescent materials and devices
WO2014030666A1 (en) 2012-08-24 2014-02-27 コニカミノルタ株式会社 Transparent electrode, electronic device, and method for manufacturing transparent electrode
US9978958B2 (en) 2012-08-24 2018-05-22 Universal Display Corporation Phosphorescent emitters with phenylimidazole ligands
US8952362B2 (en) 2012-08-31 2015-02-10 The Regents Of The University Of Michigan High efficiency and brightness fluorescent organic light emitting diode by triplet-triplet fusion
US11696459B2 (en) 2012-09-07 2023-07-04 Universal Display Corporation Phosphorescence-sensitized delayed fluorescence light emitting system
US10957870B2 (en) 2012-09-07 2021-03-23 Universal Display Corporation Organic light emitting device
US9287513B2 (en) 2012-09-24 2016-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US10388894B2 (en) 2012-09-25 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US11917902B2 (en) 2012-09-25 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US9312505B2 (en) 2012-09-25 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9252363B2 (en) 2012-10-04 2016-02-02 Universal Display Corporation Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers
US8692241B1 (en) 2012-11-08 2014-04-08 Universal Display Corporation Transition metal complexes containing triazole and tetrazole carbene ligands
US10033002B2 (en) 2012-11-09 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US10510968B2 (en) 2012-11-09 2019-12-17 Universal Display Corporation Organic electroluminescent materials and devices
US11380855B2 (en) 2012-11-09 2022-07-05 Universal Display Corporation Organic electroluminescent materials and devices
US9685617B2 (en) 2012-11-09 2017-06-20 Universal Display Corporation Organic electronuminescent materials and devices
US8946697B1 (en) 2012-11-09 2015-02-03 Universal Display Corporation Iridium complexes with aza-benzo fused ligands
US9634264B2 (en) 2012-11-09 2017-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US10069090B2 (en) 2012-11-20 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US9190623B2 (en) 2012-11-20 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US11145831B2 (en) 2012-11-20 2021-10-12 Universal Display Corporation Osmium(IV) complexes for OLED materials
US10847729B2 (en) 2012-11-20 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US9512136B2 (en) 2012-11-26 2016-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US9166175B2 (en) 2012-11-27 2015-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US9196860B2 (en) 2012-12-04 2015-11-24 Universal Display Corporation Compounds for triplet-triplet annihilation upconversion
US8716484B1 (en) 2012-12-05 2014-05-06 Universal Display Corporation Hole transporting materials with twisted aryl groups
US9209411B2 (en) 2012-12-07 2015-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US11716902B2 (en) 2012-12-07 2023-08-01 Universal Display Corporation Organic electroluminescent materials and devices
US10069081B2 (en) 2012-12-07 2018-09-04 Universal Display Corporation Organic electroluminescent materials and devices
US10910564B2 (en) 2012-12-07 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US9670185B2 (en) 2012-12-07 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US10411199B2 (en) 2012-12-12 2019-09-10 Samsung Electronics Co., Ltd. Organometallic complexes, and organic electroluminescent device and display using the same
US9653691B2 (en) 2012-12-12 2017-05-16 Universal Display Corporation Phosphorescence-sensitizing fluorescence material system
US10400163B2 (en) 2013-02-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US9935276B2 (en) 2013-02-21 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US10367154B2 (en) 2013-02-21 2019-07-30 Universal Display Corporation Organic electroluminescent materials and devices
US11871652B2 (en) 2013-02-21 2024-01-09 Universal Display Corporation Organic electroluminescent materials and devices
US8927749B2 (en) 2013-03-07 2015-01-06 Universal Display Corporation Organic electroluminescent materials and devices
WO2014138912A1 (en) * 2013-03-13 2014-09-18 Queen's University At Kingston Luminescent compounds and methods of using same
US9419225B2 (en) 2013-03-14 2016-08-16 Universal Display Corporation Organic electroluminescent materials and devices
US9997712B2 (en) 2013-03-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
WO2014157494A1 (en) 2013-03-29 2014-10-02 コニカミノルタ株式会社 Material for organic electroluminescent elements, organic electroluminescent element, display device and lighting device
WO2014157618A1 (en) 2013-03-29 2014-10-02 コニカミノルタ株式会社 Organic electroluminescent element, and lighting device and display device which are provided with same
JP2016520576A (en) * 2013-04-29 2016-07-14 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Transition metal complexes with carbene ligands and their use in OLEDs
US9537106B2 (en) 2013-05-09 2017-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US9735373B2 (en) 2013-06-10 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9673401B2 (en) 2013-06-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US10199581B2 (en) 2013-07-01 2019-02-05 Universal Display Corporation Organic electroluminescent materials and devices
US10991896B2 (en) 2013-07-01 2021-04-27 Universal Display Corporation Organic electroluminescent materials and devices
US10121975B2 (en) 2013-07-03 2018-11-06 Universal Display Corporation Organic electroluminescent materials and devices
US9761807B2 (en) 2013-07-15 2017-09-12 Universal Display Corporation Organic light emitting diode materials
US9324949B2 (en) 2013-07-16 2016-04-26 Universal Display Corporation Organic electroluminescent materials and devices
US9553274B2 (en) 2013-07-16 2017-01-24 Universal Display Corporation Organic electroluminescent materials and devices
US9224958B2 (en) 2013-07-19 2015-12-29 Universal Display Corporation Organic electroluminescent materials and devices
US10930866B2 (en) 2013-07-25 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US9831437B2 (en) 2013-08-20 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US10749114B2 (en) 2013-08-20 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10074806B2 (en) 2013-08-20 2018-09-11 Universal Display Corporation Organic electroluminescent materials and devices
US11611042B2 (en) 2013-08-20 2023-03-21 Universal Display Corporation Organic electroluminescent materials and devices
US9932359B2 (en) 2013-08-30 2018-04-03 University Of Southern California Organic electroluminescent materials and devices
US10199582B2 (en) 2013-09-03 2019-02-05 University Of Southern California Organic electroluminescent materials and devices
US9735378B2 (en) 2013-09-09 2017-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US9748503B2 (en) 2013-09-13 2017-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US10003034B2 (en) 2013-09-30 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US9831447B2 (en) 2013-10-08 2017-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US9293712B2 (en) 2013-10-11 2016-03-22 Universal Display Corporation Disubstituted pyrene compounds with amino group containing ortho aryl group and devices containing the same
US10128450B2 (en) 2013-10-23 2018-11-13 University Of Southern California Organic electroluminescent materials and devices
US9853229B2 (en) 2013-10-23 2017-12-26 University Of Southern California Organic electroluminescent materials and devices
US11944000B2 (en) 2013-10-29 2024-03-26 Universal Display Corporation Organic electroluminescent materials and devices
US9865824B2 (en) 2013-11-07 2018-01-09 Industrial Technology Research Institute Organometallic compound, organic light-emitting device, and lighting device employing the same
US9306179B2 (en) 2013-11-08 2016-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US9647218B2 (en) 2013-11-14 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9905784B2 (en) 2013-11-15 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US10056565B2 (en) 2013-11-20 2018-08-21 Universal Display Corporation Organic electroluminescent materials and devices
US9812653B2 (en) 2013-11-28 2017-11-07 Samsung Electronics Co., Ltd. Carbazole compound and organic light-emitting device including the same
US10644251B2 (en) 2013-12-04 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
US9876173B2 (en) 2013-12-09 2018-01-23 Universal Display Corporation Organic electroluminescent materials and devices
US11653558B2 (en) 2013-12-16 2023-05-16 Universal Display Corporation Organic electroluminescent materials and devices
US10355227B2 (en) 2013-12-16 2019-07-16 Universal Display Corporation Metal complex for phosphorescent OLED
US9847496B2 (en) 2013-12-23 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US10135008B2 (en) 2014-01-07 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US11943999B2 (en) 2014-01-07 2024-03-26 Universal Display Corporation Organic electroluminescent materials and devices
US10749122B2 (en) 2014-01-07 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10985331B2 (en) 2014-01-07 2021-04-20 Universal Display Corporation Organic electroluminescent materials and devices
US9812657B2 (en) 2014-01-07 2017-11-07 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
US11005051B2 (en) 2014-01-08 2021-05-11 Universal Display Corporation Organic electroluminescent materials and devices
US9978961B2 (en) 2014-01-08 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US9755159B2 (en) 2014-01-23 2017-09-05 Universal Display Corporation Organic materials for OLEDs
US9935277B2 (en) 2014-01-30 2018-04-03 Universal Display Corporation Organic electroluminescent materials and devices
US9590194B2 (en) 2014-02-14 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US10003033B2 (en) 2014-02-18 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US9847497B2 (en) 2014-02-18 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US11024816B2 (en) 2014-02-18 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US10707423B2 (en) 2014-02-21 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US9647217B2 (en) 2014-02-24 2017-05-09 Universal Display Corporation Organic electroluminescent materials and devices
US9502656B2 (en) 2014-02-24 2016-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US10403825B2 (en) 2014-02-27 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US11600782B2 (en) 2014-02-27 2023-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9181270B2 (en) 2014-02-28 2015-11-10 Universal Display Corporation Method of making sulfide compounds
US9673407B2 (en) 2014-02-28 2017-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US9590195B2 (en) 2014-02-28 2017-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US9190620B2 (en) 2014-03-01 2015-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US9397309B2 (en) 2014-03-13 2016-07-19 Universal Display Corporation Organic electroluminescent devices
US10208026B2 (en) 2014-03-18 2019-02-19 Universal Display Corporation Organic electroluminescent materials and devices
US9929353B2 (en) 2014-04-02 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US9691993B2 (en) 2014-04-09 2017-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US10825998B2 (en) 2014-04-14 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US9847498B2 (en) 2014-04-14 2017-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US10008679B2 (en) 2014-04-14 2018-06-26 Universal Display Corporation Organic electroluminescent materials and devices
US11005052B2 (en) 2014-04-14 2021-05-11 Universal Display Corporation Organic electroluminescent materials and devices
US9905785B2 (en) 2014-04-14 2018-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11793066B2 (en) 2014-04-14 2023-10-17 Universal Display Corporation Organic electroluminescent materials and devices
US9450198B2 (en) 2014-04-15 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US10256427B2 (en) 2014-04-15 2019-04-09 Universal Display Corporation Efficient organic electroluminescent devices
US9741941B2 (en) 2014-04-29 2017-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US10457699B2 (en) 2014-05-02 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US11427607B2 (en) 2014-05-02 2022-08-30 Universal Display Corporation Organic electroluminescent materials and devices
US11919916B2 (en) 2014-05-02 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US10263198B2 (en) 2014-05-08 2019-04-16 Universal Display Corporation Organic electroluminescent materials and devices
US10301338B2 (en) 2014-05-08 2019-05-28 Universal Display Corporation Organic electroluminescent materials and devices
US10403830B2 (en) 2014-05-08 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10636983B2 (en) 2014-05-08 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US10276805B2 (en) 2014-05-08 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US11495754B2 (en) 2014-05-08 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US10256419B2 (en) 2014-05-08 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US9997716B2 (en) 2014-05-27 2018-06-12 Universal Display Corporation Organic electroluminescent materials and devices
US10461260B2 (en) 2014-06-03 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US10700293B2 (en) 2014-06-26 2020-06-30 Universal Display Corporation Organic electroluminescent materials and devices
US9911931B2 (en) 2014-06-26 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US10297762B2 (en) 2014-07-09 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US11024811B2 (en) 2014-07-09 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US11456423B2 (en) 2014-07-09 2022-09-27 Universal Display Corporation Organic electroluminescent materials and devices
US10566546B2 (en) 2014-07-14 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US9929357B2 (en) 2014-07-22 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US11108000B2 (en) 2014-08-07 2021-08-31 Unniversal Display Corporation Organic electroluminescent materials and devices
US10411200B2 (en) 2014-08-07 2019-09-10 Universal Display Corporation Electroluminescent (2-phenylpyridine)iridium complexes and devices
US10749113B2 (en) 2014-09-29 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US11641774B2 (en) 2014-09-29 2023-05-02 Universal Display Corporation Organic electroluminescent materials and devices
US10043987B2 (en) 2014-09-29 2018-08-07 Universal Display Corporation Organic electroluminescent materials and devices
US10135007B2 (en) 2014-09-29 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
US11342510B2 (en) 2014-10-06 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US10361375B2 (en) 2014-10-06 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US11342516B2 (en) 2014-10-08 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US9397302B2 (en) 2014-10-08 2016-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US9799838B2 (en) 2014-10-08 2017-10-24 Universal Display Corporation Fluorinated organic electroluminescent materials and devices
US10854826B2 (en) 2014-10-08 2020-12-01 Universal Display Corporation Organic electroluminescent compounds, compositions and devices
US10998508B2 (en) 2014-10-08 2021-05-04 Universal Display Corporation Organic electroluminescent materials and devices
US10950803B2 (en) 2014-10-13 2021-03-16 Universal Display Corporation Compounds and uses in devices
US9484541B2 (en) 2014-10-20 2016-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US10868261B2 (en) 2014-11-10 2020-12-15 Universal Display Corporation Organic electroluminescent materials and devices
US10038151B2 (en) 2014-11-12 2018-07-31 Universal Display Corporation Organic electroluminescent materials and devices
US11832507B2 (en) 2014-11-12 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US10411201B2 (en) 2014-11-12 2019-09-10 Universal Display Corporation Organic electroluminescent materials and devices
US11043641B2 (en) 2014-11-12 2021-06-22 Universal Display Corporation Organic electroluminescent materials and devices
US9882151B2 (en) 2014-11-14 2018-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US9871212B2 (en) 2014-11-14 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
US9761814B2 (en) 2014-11-18 2017-09-12 Universal Display Corporation Organic light-emitting materials and devices
US9444075B2 (en) 2014-11-26 2016-09-13 Universal Display Corporation Emissive display with photo-switchable polarization
US9825260B2 (en) 2014-11-26 2017-11-21 Universal Display Corporation Emissive display with photo-switchable polarization
US10000517B2 (en) 2014-12-17 2018-06-19 Universal Display Corporation Organic electroluminescent materials and devices
US9450195B2 (en) 2014-12-17 2016-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US9680113B2 (en) 2014-12-17 2017-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US10253252B2 (en) 2014-12-30 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10636978B2 (en) 2014-12-30 2020-04-28 Universal Display Corporation Organic electroluminescent materials and devices
US9312499B1 (en) 2015-01-05 2016-04-12 Universal Display Corporation Organic electroluminescent materials and devices
US9406892B2 (en) 2015-01-07 2016-08-02 Universal Display Corporation Organic electroluminescent materials and devices
US9748500B2 (en) 2015-01-15 2017-08-29 Universal Display Corporation Organic light emitting materials
US10418569B2 (en) 2015-01-25 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US9711730B2 (en) 2015-01-25 2017-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US10418562B2 (en) 2015-02-06 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10355222B2 (en) 2015-02-06 2019-07-16 Universal Display Corporation Organic electroluminescent materials and devices
US10644247B2 (en) 2015-02-06 2020-05-05 Universal Display Corporation Organic electroluminescent materials and devices
US11245081B2 (en) 2015-02-06 2022-02-08 Universal Display Corporation Organic electroluminescent materials and devices
US10177316B2 (en) 2015-02-09 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US11535797B2 (en) 2015-02-13 2022-12-27 Universal Display Corporation Organic electroluminescent materials and devices
EP4271160A2 (en) 2015-02-13 2023-11-01 Merck Patent GmbH Aromatic heterocyclic derivative, and organic electroluminescent element, illumination device, and display device using aromatic heterocyclic derivative
US10144867B2 (en) 2015-02-13 2018-12-04 Universal Display Corporation Organic electroluminescent materials and devices
US10889754B2 (en) 2015-02-13 2021-01-12 Universal Display Corporation Organic electroluminescent materials and devices
US11795385B2 (en) 2015-02-13 2023-10-24 Universal Display Corporation Organic electroluminescent materials and devices
US10680183B2 (en) 2015-02-15 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US9929361B2 (en) 2015-02-16 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US11056657B2 (en) 2015-02-27 2021-07-06 University Display Corporation Organic electroluminescent materials and devices
US10600966B2 (en) 2015-02-27 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US11678567B2 (en) 2015-02-27 2023-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US10686143B2 (en) 2015-03-05 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
US10270046B2 (en) 2015-03-06 2019-04-23 Universal Display Corporation Organic electroluminescent materials and devices
US9780316B2 (en) 2015-03-16 2017-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US9911928B2 (en) 2015-03-19 2018-03-06 Universal Display Corporation Organic electroluminescent materials and devices
US9871214B2 (en) 2015-03-23 2018-01-16 Universal Display Corporation Organic electroluminescent materials and devices
US10529931B2 (en) 2015-03-24 2020-01-07 Universal Display Corporation Organic Electroluminescent materials and devices
US10297770B2 (en) 2015-03-27 2019-05-21 Universal Display Corporation Organic electroluminescent materials and devices
US11818949B2 (en) 2015-04-06 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11245080B2 (en) 2015-04-06 2022-02-08 Universal Display Corporation Organic electroluminescent materials and devices
US10693082B2 (en) 2015-04-06 2020-06-23 Universal Display Corporation Organic electroluminescent materials and devices
US11495749B2 (en) 2015-04-06 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US10593890B2 (en) 2015-04-06 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US11672175B2 (en) 2015-04-06 2023-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US10403826B2 (en) 2015-05-07 2019-09-03 Universal Display Corporation Organic electroluminescent materials and devices
US10777749B2 (en) 2015-05-07 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
US11744151B2 (en) 2015-05-07 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US9478758B1 (en) 2015-05-08 2016-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US10547013B2 (en) 2015-05-15 2020-01-28 Universal Display Corporation Organic electroluminescent materials and devices
US11335864B2 (en) 2015-05-15 2022-05-17 Universal Display Corporation Organic electroluminescent materials and devices
US9859510B2 (en) 2015-05-15 2018-01-02 Universal Display Corporation Organic electroluminescent materials and devices
USRE48809E1 (en) 2015-05-15 2021-11-02 Universal Display Corporation Organic electroluminescent materials and devices
US10256411B2 (en) 2015-05-21 2019-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US10109799B2 (en) 2015-05-21 2018-10-23 Universal Display Corporation Organic electroluminescent materials and devices
US10418568B2 (en) 2015-06-01 2019-09-17 Universal Display Corporation Organic electroluminescent materials and devices
US10033004B2 (en) 2015-06-01 2018-07-24 Universal Display Corporation Organic electroluminescent materials and devices
US11925102B2 (en) 2015-06-04 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US10825997B2 (en) 2015-06-25 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US10873036B2 (en) 2015-07-07 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US9978956B2 (en) 2015-07-15 2018-05-22 Universal Display Corporation Organic electroluminescent materials and devices
US11127905B2 (en) 2015-07-29 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11018309B2 (en) 2015-08-03 2021-05-25 Universal Display Corporation Organic electroluminescent materials and devices
US11522140B2 (en) 2015-08-17 2022-12-06 Universal Display Corporation Organic electroluminescent materials and devices
US10522769B2 (en) 2015-08-18 2019-12-31 Universal Display Corporation Organic electroluminescent materials and devices
US10181564B2 (en) 2015-08-26 2019-01-15 Universal Display Corporation Organic electroluminescent materials and devices
US11626563B2 (en) 2015-09-03 2023-04-11 Universal Display Corporation Organic electroluminescent materials and devices
US10361381B2 (en) 2015-09-03 2019-07-23 Universal Display Corporation Organic electroluminescent materials and devices
US10672996B2 (en) 2015-09-03 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US11605789B2 (en) 2015-09-03 2023-03-14 Universal Display Corporation Organic electroluminescent materials and devices
US11706972B2 (en) 2015-09-08 2023-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US11302872B2 (en) 2015-09-09 2022-04-12 Universal Display Corporation Organic electroluminescent materials and devices
JP2016036032A (en) * 2015-09-14 2016-03-17 コニカミノルタ株式会社 Organic electroluminescent element, display device and illuminating device
US10770664B2 (en) 2015-09-21 2020-09-08 Universal Display Corporation Organic electroluminescent materials and devices
US11812622B2 (en) 2015-09-25 2023-11-07 Universal Display Corporation Organic electroluminescent compounds and devices
US11889747B2 (en) 2015-10-01 2024-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US10847728B2 (en) 2015-10-01 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US10593892B2 (en) 2015-10-01 2020-03-17 Universal Display Corporation Organic electroluminescent materials and devices
US10991895B2 (en) 2015-10-06 2021-04-27 Universal Display Corporation Organic electroluminescent materials and devices
US11349087B2 (en) 2015-10-29 2022-05-31 Universal Display Corporation Organic electroluminescent materials and devices
US10177318B2 (en) 2015-10-29 2019-01-08 Universal Display Corporation Organic electroluminescent materials and devices
US10388893B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US10388892B2 (en) 2015-10-29 2019-08-20 Universal Display Corporation Organic electroluminescent materials and devices
US11832456B2 (en) 2015-11-23 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US10998507B2 (en) 2015-11-23 2021-05-04 Universal Display Corporation Organic electroluminescent materials and devices
US10476010B2 (en) 2015-11-30 2019-11-12 Universal Display Corporation Organic electroluminescent materials and devices
CN105524114A (en) * 2015-12-24 2016-04-27 石家庄诚志永华显示材料有限公司 Series of deep blue metal iridium phosphorescence OLED materials
US10957861B2 (en) 2015-12-29 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US11818948B2 (en) 2015-12-29 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11024808B2 (en) 2015-12-29 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US10135006B2 (en) 2016-01-04 2018-11-20 Universal Display Corporation Organic electroluminescent materials and devices
EP3200255A2 (en) 2016-01-06 2017-08-02 Konica Minolta, Inc. Organic electroluminescent element, method for producing organic electroluminescent element, display, and lighting device
US10707427B2 (en) 2016-02-09 2020-07-07 Universal Display Corporation Organic electroluminescent materials and devices
US11098245B2 (en) 2016-02-09 2021-08-24 Universal Display Corporation Organic electroluminescent materials and devices
US10457864B2 (en) 2016-02-09 2019-10-29 Universal Display Corporation Organic electroluminescent materials and devices
US11716898B2 (en) 2016-02-09 2023-08-01 Universal Display Corporation Organic electroluminescent materials and devices
US11692132B2 (en) 2016-02-09 2023-07-04 Universal Display Corporation Organic electroluminescent materials and devices
US10600967B2 (en) 2016-02-18 2020-03-24 Universal Display Corporation Organic electroluminescent materials and devices
US11094891B2 (en) 2016-03-16 2021-08-17 Universal Display Corporation Organic electroluminescent materials and devices
US10276809B2 (en) 2016-04-05 2019-04-30 Universal Display Corporation Organic electroluminescent materials and devices
US10236456B2 (en) 2016-04-11 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11342515B2 (en) 2016-04-13 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11825734B2 (en) 2016-04-13 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US10566552B2 (en) 2016-04-13 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US11228003B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11081647B2 (en) 2016-04-22 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11228002B2 (en) 2016-04-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US10985328B2 (en) 2016-05-25 2021-04-20 Universal Display Corporation Organic electroluminescent materials and devices
US10840458B2 (en) 2016-05-25 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US11711977B2 (en) 2016-05-25 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US10468609B2 (en) 2016-06-02 2019-11-05 Universal Display Corporation Organic electroluminescent materials and devices
US11903306B2 (en) 2016-06-20 2024-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US10727423B2 (en) 2016-06-20 2020-07-28 Universal Display Corporation Organic electroluminescent materials and devices
US11839139B2 (en) 2016-06-20 2023-12-05 Universal Display Corporation Organic electroluminescent materials and devices
US10686140B2 (en) 2016-06-20 2020-06-16 Universal Display Corporation Organic electroluminescent materials and devices
US11424419B2 (en) 2016-06-20 2022-08-23 Universal Display Corporation Organic electroluminescent materials and devices
US10651403B2 (en) 2016-06-20 2020-05-12 Universal Display Corporation Organic electroluminescent materials and devices
US11114624B2 (en) 2016-06-20 2021-09-07 Universal Display Corporation Organic electroluminescent materials and devices
US11683981B2 (en) 2016-06-20 2023-06-20 Universal Display Corporation Organic electroluminescent materials and devices
US11588121B2 (en) 2016-06-20 2023-02-21 Universal Display Corporation Organic electroluminescent materials and devices
US10862054B2 (en) 2016-06-20 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US11690284B2 (en) 2016-06-20 2023-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US11482683B2 (en) 2016-06-20 2022-10-25 Universal Display Corporation Organic electroluminescent materials and devices
US10672997B2 (en) 2016-06-20 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US10957866B2 (en) 2016-06-30 2021-03-23 Universal Display Corporation Organic electroluminescent materials and devices
US9929360B2 (en) 2016-07-08 2018-03-27 Universal Display Corporation Organic electroluminescent materials and devices
US10680184B2 (en) 2016-07-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10566547B2 (en) 2016-07-11 2020-02-18 Universal Display Corporation Organic electroluminescent materials and devices
US10153443B2 (en) 2016-07-19 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US10720587B2 (en) 2016-07-19 2020-07-21 Universal Display Corporation Organic electroluminescent materials and devices
US10205105B2 (en) 2016-08-15 2019-02-12 Universal Display Corporation Organic electroluminescent materials and devices
US10608186B2 (en) 2016-09-14 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US11024807B2 (en) 2016-09-14 2021-06-01 Universal Display Corporation Organic electroluminescent materials and devices
US10505127B2 (en) 2016-09-19 2019-12-10 Universal Display Corporation Organic electroluminescent materials and devices
US10680187B2 (en) 2016-09-23 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US11711969B2 (en) 2016-10-03 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11127906B2 (en) 2016-10-03 2021-09-21 Universal Display Corporation Organic electroluminescent materials and devices
US11081658B2 (en) 2016-10-03 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11183642B2 (en) 2016-10-03 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11196010B2 (en) 2016-10-03 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US11189804B2 (en) 2016-10-03 2021-11-30 Universal Display Corporation Organic electroluminescent materials and devices
US11711968B2 (en) 2016-10-07 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11011709B2 (en) 2016-10-07 2021-05-18 Universal Display Corporation Organic electroluminescent materials and devices
US11239432B2 (en) 2016-10-14 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US10608185B2 (en) 2016-10-17 2020-03-31 Univeral Display Corporation Organic electroluminescent materials and devices
US10236458B2 (en) 2016-10-24 2019-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US10340464B2 (en) 2016-11-10 2019-07-02 Universal Display Corporation Organic electroluminescent materials and devices
US11069864B2 (en) 2016-11-11 2021-07-20 Universal Display Corporation Organic electroluminescent materials and devices
US10680188B2 (en) 2016-11-11 2020-06-09 Universal Display Corporation Organic electroluminescent materials and devices
US10897016B2 (en) 2016-11-14 2021-01-19 Universal Display Corporation Organic electroluminescent materials and devices
US10964893B2 (en) 2016-11-17 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US10662196B2 (en) 2016-11-17 2020-05-26 Universal Display Corporation Organic electroluminescent materials and devices
US10833276B2 (en) 2016-11-21 2020-11-10 Universal Display Corporation Organic electroluminescent materials and devices
US10153445B2 (en) 2016-11-21 2018-12-11 Universal Display Corporation Organic electroluminescent materials and devices
US11555048B2 (en) 2016-12-01 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US10490753B2 (en) 2016-12-15 2019-11-26 Universal Display Corporation Organic electroluminescent materials and devices
US11548905B2 (en) 2016-12-15 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US11545636B2 (en) 2016-12-15 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US10811618B2 (en) 2016-12-19 2020-10-20 Universal Display Corporation Organic electroluminescent materials and devices
US11152579B2 (en) 2016-12-28 2021-10-19 Universal Display Corporation Organic electroluminescent materials and devices
US11780865B2 (en) 2017-01-09 2023-10-10 Universal Display Corporation Organic electroluminescent materials and devices
US11201298B2 (en) 2017-01-09 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US10804475B2 (en) 2017-01-11 2020-10-13 Universal Display Corporation Organic electroluminescent materials and devices
US11545637B2 (en) 2017-01-13 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US10629820B2 (en) 2017-01-18 2020-04-21 Universal Display Corporation Organic electroluminescent materials and devices
US10964904B2 (en) 2017-01-20 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US11566034B2 (en) 2017-01-20 2023-01-31 Universal Display Corporation Organic electroluminescent materials and devices
US11053268B2 (en) 2017-01-20 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US11765968B2 (en) 2017-01-23 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11050028B2 (en) 2017-01-24 2021-06-29 Universal Display Corporation Organic electroluminescent materials and devices
US11765966B2 (en) 2017-01-24 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US10978647B2 (en) 2017-02-15 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US10844084B2 (en) 2017-02-22 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US11254697B2 (en) 2017-02-22 2022-02-22 Universal Display Corporation Organic electroluminescent materials and devices
US10822361B2 (en) 2017-02-22 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US11760770B2 (en) 2017-02-22 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11697661B2 (en) 2017-02-22 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US10923667B2 (en) 2017-03-08 2021-02-16 Samsung Electronics Co., Ltd. Organometallic compound, composition containing the organometallic compound, and organic light-emitting device including the organometallic compound
US10745431B2 (en) 2017-03-08 2020-08-18 Universal Display Corporation Organic electroluminescent materials and devices
US10741780B2 (en) 2017-03-10 2020-08-11 Universal Display Corporation Organic electroluminescent materials and devices
US10672998B2 (en) 2017-03-23 2020-06-02 Universal Display Corporation Organic electroluminescent materials and devices
US10910577B2 (en) 2017-03-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US10873037B2 (en) 2017-03-28 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US11678563B2 (en) 2017-03-29 2023-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US11056658B2 (en) 2017-03-29 2021-07-06 Universal Display Corporation Organic electroluminescent materials and devices
US11725021B2 (en) 2017-03-29 2023-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US10844085B2 (en) 2017-03-29 2020-11-24 Universal Display Corporation Organic electroluminescent materials and devices
US11158820B2 (en) 2017-03-29 2021-10-26 Universal Display Corporation Organic electroluminescent materials and devices
US11192910B2 (en) 2017-03-29 2021-12-07 Universal Display Corporation Organic electroluminescent materials and devices
US10862046B2 (en) 2017-03-30 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US11276829B2 (en) 2017-03-31 2022-03-15 Universal Display Corporation Organic electroluminescent materials and devices
US11139443B2 (en) 2017-03-31 2021-10-05 Universal Display Corporation Organic electroluminescent materials and devices
US11038117B2 (en) 2017-04-11 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US10777754B2 (en) 2017-04-11 2020-09-15 Universal Display Corporation Organic electroluminescent materials and devices
US11101434B2 (en) 2017-04-21 2021-08-24 Universal Display Corporation Organic electroluminescent materials and devices
US11591356B2 (en) 2017-04-21 2023-02-28 Universal Display Corporation Organic electroluminescent materials and devices
US10975113B2 (en) 2017-04-21 2021-04-13 Universal Display Corporation Organic electroluminescent materials and devices
US11084838B2 (en) 2017-04-21 2021-08-10 Universal Display Corporation Organic electroluminescent materials and device
US11566035B2 (en) 2017-04-21 2023-01-31 Universal Display Corporation Organic electroluminescent materials and devices
US10910570B2 (en) 2017-04-28 2021-02-02 Universal Display Corporation Organic electroluminescent materials and devices
US11038137B2 (en) 2017-04-28 2021-06-15 Universal Display Corporation Organic electroluminescent materials and devices
US11702420B2 (en) 2017-05-01 2023-07-18 Universal Display Corporation Organic electroluminescent materials and devices
US11117897B2 (en) 2017-05-01 2021-09-14 Universal Display Corporation Organic electroluminescent materials and devices
US10941170B2 (en) 2017-05-03 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US11201299B2 (en) 2017-05-04 2021-12-14 Universal Display Corporation Organic electroluminescent materials and devices
US10862055B2 (en) 2017-05-05 2020-12-08 Universal Display Corporation Organic electroluminescent materials and devices
US10870668B2 (en) 2017-05-05 2020-12-22 Universal Display Corporation Organic electroluminescent materials and devices
US11377459B2 (en) 2017-05-05 2022-07-05 Universal Display Corporation Organic electroluminescent materials and devices
US10930864B2 (en) 2017-05-10 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10944060B2 (en) 2017-05-11 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10822362B2 (en) 2017-05-11 2020-11-03 Universal Display Corporation Organic electroluminescent materials and devices
US11038115B2 (en) 2017-05-18 2021-06-15 Universal Display Corporation Organic electroluminescent materials and device
US10944062B2 (en) 2017-05-18 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
US10790455B2 (en) 2017-05-18 2020-09-29 Universal Display Corporation Organic electroluminescent materials and devices
US10934293B2 (en) 2017-05-18 2021-03-02 Universal Display Corporation Organic electroluminescent materials and devices
US10840459B2 (en) 2017-05-18 2020-11-17 Universal Display Corporation Organic electroluminescent materials and devices
US10930862B2 (en) 2017-06-01 2021-02-23 Universal Display Corporation Organic electroluminescent materials and devices
US10968226B2 (en) 2017-06-23 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US11832510B2 (en) 2017-06-23 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US11608321B2 (en) 2017-06-23 2023-03-21 Universal Display Corporation Organic electroluminescent materials and devices
US11552261B2 (en) 2017-06-23 2023-01-10 Universal Display Corporation Organic electroluminescent materials and devices
US11731975B2 (en) 2017-06-23 2023-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US11495757B2 (en) 2017-06-23 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11802136B2 (en) 2017-06-23 2023-10-31 Universal Display Corporation Organic electroluminescent materials and devices
US11758804B2 (en) 2017-06-23 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11174259B2 (en) 2017-06-23 2021-11-16 Universal Display Corporation Organic electroluminescent materials and devices
US11678565B2 (en) 2017-06-23 2023-06-13 Universal Display Corporation Organic electroluminescent materials and devices
US11725022B2 (en) 2017-06-23 2023-08-15 Universal Display Corporation Organic electroluminescent materials and devices
US11814403B2 (en) 2017-06-23 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11469382B2 (en) 2017-07-12 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11322691B2 (en) 2017-07-26 2022-05-03 Universal Display Corporation Organic electroluminescent materials and devices
US11917843B2 (en) 2017-07-26 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11765970B2 (en) 2017-07-26 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11239433B2 (en) 2017-07-26 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11228010B2 (en) 2017-07-26 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11744141B2 (en) 2017-08-09 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11349083B2 (en) 2017-08-10 2022-05-31 Universal Display Corporation Organic electroluminescent materials and devices
US11744142B2 (en) 2017-08-10 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11508913B2 (en) 2017-08-10 2022-11-22 Universal Display Corporation Organic electroluminescent materials and devices
US11910699B2 (en) 2017-08-10 2024-02-20 Universal Display Corporation Organic electroluminescent materials and devices
KR20190020872A (en) * 2017-08-21 2019-03-05 삼성디스플레이 주식회사 Cyclometallic compound, organic light emitting device comprising the same and emitting apparatus comprising the organic light emitting device
CN109422775A (en) * 2017-08-21 2019-03-05 三星显示有限公司 Organo-metallic compound, organic luminescent device and organic light emitting apparatus
CN109422775B (en) * 2017-08-21 2024-03-19 三星显示有限公司 Organometallic compound, organic light-emitting device, and organic light-emitting device
KR102504132B1 (en) * 2017-08-21 2023-02-28 삼성디스플레이 주식회사 Cyclometallic compound, organic light emitting device comprising the same and emitting apparatus comprising the organic light emitting device
US11723269B2 (en) 2017-08-22 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11462697B2 (en) 2017-08-22 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US11437591B2 (en) 2017-08-24 2022-09-06 Universal Display Corporation Organic electroluminescent materials and devices
US11605791B2 (en) 2017-09-01 2023-03-14 Universal Display Corporation Organic electroluminescent materials and devices
US11696492B2 (en) 2017-09-07 2023-07-04 Universal Display Corporation Organic electroluminescent materials and devices
US11444249B2 (en) 2017-09-07 2022-09-13 Universal Display Corporation Organic electroluminescent materials and devices
US11424420B2 (en) 2017-09-07 2022-08-23 Universal Display Corporation Organic electroluminescent materials and devices
US10964895B2 (en) 2017-09-11 2021-03-30 Universal Display Corporation Organic electroluminescent materials and devices
US10608188B2 (en) 2017-09-11 2020-03-31 Universal Display Corporation Organic electroluminescent materials and devices
US11778897B2 (en) 2017-09-20 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
CN107722060A (en) * 2017-09-30 2018-02-23 南京邮电大学 A kind of fluorenyl tetrazole complex of iridium and its preparation method and application
US11183646B2 (en) 2017-11-07 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11214587B2 (en) 2017-11-07 2022-01-04 Universal Display Corporation Organic electroluminescent materials and devices
US11685756B2 (en) 2017-11-07 2023-06-27 Universal Display Corporation Organic electroluminescent materials and devices
US11910702B2 (en) 2017-11-07 2024-02-20 Universal Display Corporation Organic electroluminescent devices
US11168103B2 (en) 2017-11-17 2021-11-09 Universal Display Corporation Organic electroluminescent materials and devices
US11825735B2 (en) 2017-11-28 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11937503B2 (en) 2017-11-30 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11233205B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US10971687B2 (en) 2017-12-14 2021-04-06 Universal Display Corporation Organic electroluminescent materials and devices
US11233204B2 (en) 2017-12-14 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11700765B2 (en) 2018-01-10 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11081659B2 (en) 2018-01-10 2021-08-03 Universal Display Corporation Organic electroluminescent materials and devices
US11271177B2 (en) 2018-01-11 2022-03-08 Universal Display Corporation Organic electroluminescent materials and devices
US11818946B2 (en) 2018-01-11 2023-11-14 Universal Display Corporation Organic electroluminescent materials and devices
US11515493B2 (en) 2018-01-11 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11367840B2 (en) 2018-01-26 2022-06-21 Universal Display Corporation Organic electroluminescent materials and devices
US11542289B2 (en) 2018-01-26 2023-01-03 Universal Display Corporation Organic electroluminescent materials and devices
US11845764B2 (en) 2018-01-26 2023-12-19 Universal Display Corporation Organic electroluminescent materials and devices
US11697662B2 (en) 2018-02-09 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11239434B2 (en) 2018-02-09 2022-02-01 Universal Display Corporation Organic electroluminescent materials and devices
US11180519B2 (en) 2018-02-09 2021-11-23 Universal Display Corporation Organic electroluminescent materials and devices
US11342509B2 (en) 2018-02-09 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11910708B2 (en) 2018-02-09 2024-02-20 Universal Display Corporation Organic electroluminescent materials and devices
US11557733B2 (en) 2018-03-12 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11217757B2 (en) 2018-03-12 2022-01-04 Universal Display Corporation Host materials for electroluminescent devices
US11142538B2 (en) 2018-03-12 2021-10-12 Universal Display Corporation Organic electroluminescent materials and devices
US11746122B2 (en) 2018-03-12 2023-09-05 Universal Display Corporation Organic electroluminescent materials and devices
US11700766B2 (en) 2018-03-12 2023-07-11 Universal Display Corporation Host materials for electroluminescent devices
US11279722B2 (en) 2018-03-12 2022-03-22 Universal Display Corporation Organic electroluminescent materials and devices
US11165028B2 (en) 2018-03-12 2021-11-02 Universal Display Corporation Organic electroluminescent materials and devices
US11390639B2 (en) 2018-04-13 2022-07-19 Universal Display Corporation Organic electroluminescent materials and devices
US11882759B2 (en) 2018-04-13 2024-01-23 Universal Display Corporation Organic electroluminescent materials and devices
US11616203B2 (en) 2018-04-17 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices
US11515494B2 (en) 2018-05-04 2022-11-29 Universal Display Corporation Organic electroluminescent materials and devices
US11753427B2 (en) 2018-05-04 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11839142B2 (en) 2018-05-04 2023-12-05 Universal Display Corporation Organic electroluminescent materials and devices
US11342513B2 (en) 2018-05-04 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11793073B2 (en) 2018-05-06 2023-10-17 Universal Display Corporation Host materials for electroluminescent devices
US11450822B2 (en) 2018-05-25 2022-09-20 Universal Display Corporation Organic electroluminescent materials and devices
US11459349B2 (en) 2018-05-25 2022-10-04 Universal Display Corporation Organic electroluminescent materials and devices
US11844267B2 (en) 2018-05-25 2023-12-12 Universal Display Corporation Organic electroluminescent materials and devices
US11716900B2 (en) 2018-05-30 2023-08-01 Universal Display Corporation Host materials for electroluminescent devices
US11296283B2 (en) 2018-06-04 2022-04-05 Universal Display Corporation Organic electroluminescent materials and devices
US11404653B2 (en) 2018-06-04 2022-08-02 Universal Display Corporation Organic electroluminescent materials and devices
US11925103B2 (en) 2018-06-05 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11339182B2 (en) 2018-06-07 2022-05-24 Universal Display Corporation Organic electroluminescent materials and devices
US11228004B2 (en) 2018-06-22 2022-01-18 Universal Display Corporation Organic electroluminescent materials and devices
US11261207B2 (en) 2018-06-25 2022-03-01 Universal Display Corporation Organic electroluminescent materials and devices
US11753425B2 (en) 2018-07-11 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11233203B2 (en) 2018-09-06 2022-01-25 Universal Display Corporation Organic electroluminescent materials and devices
US11939293B2 (en) 2018-09-11 2024-03-26 Universal Display Corporation Organic electroluminescent materials and devices
US11485706B2 (en) 2018-09-11 2022-11-01 Universal Display Corporation Organic electroluminescent materials and devices
US11718634B2 (en) 2018-09-14 2023-08-08 Universal Display Corporation Organic electroluminescent materials and devices
US11903305B2 (en) 2018-09-24 2024-02-13 Universal Display Corporation Organic electroluminescent materials and devices
US11495752B2 (en) 2018-10-08 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11469383B2 (en) 2018-10-08 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11476430B2 (en) 2018-10-15 2022-10-18 Universal Display Corporation Organic electroluminescent materials and devices
US11515482B2 (en) 2018-10-23 2022-11-29 Universal Display Corporation Deep HOMO (highest occupied molecular orbital) emitter device structures
US11839141B2 (en) 2018-11-02 2023-12-05 Universal Display Corporation Organic electroluminescent materials and devices
US11469384B2 (en) 2018-11-02 2022-10-11 Universal Display Corporation Organic electroluminescent materials and devices
US11825736B2 (en) 2018-11-19 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11706980B2 (en) 2018-11-28 2023-07-18 Universal Display Corporation Host materials for electroluminescent devices
US11690285B2 (en) 2018-11-28 2023-06-27 Universal Display Corporation Electroluminescent devices
US11672165B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Organic electroluminescent materials and devices
US11515489B2 (en) 2018-11-28 2022-11-29 Universal Display Corporation Host materials for electroluminescent devices
US11672176B2 (en) 2018-11-28 2023-06-06 Universal Display Corporation Host materials for electroluminescent devices
US11716899B2 (en) 2018-11-28 2023-08-01 Universal Display Corporation Organic electroluminescent materials and devices
US11623936B2 (en) 2018-12-11 2023-04-11 Universal Display Corporation Organic electroluminescent materials and devices
US11834459B2 (en) 2018-12-12 2023-12-05 Universal Display Corporation Host materials for electroluminescent devices
US11737349B2 (en) 2018-12-12 2023-08-22 Universal Display Corporation Organic electroluminescent materials and devices
US11812624B2 (en) 2019-01-30 2023-11-07 The University Of Southern California Organic electroluminescent materials and devices
US11780829B2 (en) 2019-01-30 2023-10-10 The University Of Southern California Organic electroluminescent materials and devices
US11844266B2 (en) 2019-01-31 2023-12-12 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
US11957050B2 (en) 2019-02-08 2024-04-09 Universal Display Corporation Organic electroluminescent materials and devices
US11370809B2 (en) 2019-02-08 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11325932B2 (en) 2019-02-08 2022-05-10 Universal Display Corporation Organic electroluminescent materials and devices
US11773320B2 (en) 2019-02-21 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11871653B2 (en) 2019-02-22 2024-01-09 Universal Display Corporation Organic electroluminescent materials and devices
US11758807B2 (en) 2019-02-22 2023-09-12 Universal Display Corporation Organic electroluminescent materials and devices
US11557738B2 (en) 2019-02-22 2023-01-17 Universal Display Corporation Organic electroluminescent materials and devices
US11512093B2 (en) 2019-03-04 2022-11-29 Universal Display Corporation Compound used for organic light emitting device (OLED), consumer product and formulation
US11739081B2 (en) 2019-03-11 2023-08-29 Universal Display Corporation Organic electroluminescent materials and devices
US11637261B2 (en) 2019-03-12 2023-04-25 Universal Display Corporation Nanopatch antenna outcoupling structure for use in OLEDs
US11569480B2 (en) 2019-03-12 2023-01-31 Universal Display Corporation Plasmonic OLEDs and vertical dipole emitters
US11639363B2 (en) 2019-04-22 2023-05-02 Universal Display Corporation Organic electroluminescent materials and devices
US11613550B2 (en) 2019-04-30 2023-03-28 Universal Display Corporation Organic electroluminescent materials and devices comprising benzimidazole-containing metal complexes
US11495756B2 (en) 2019-05-07 2022-11-08 Universal Display Corporation Organic electroluminescent materials and devices
US11827651B2 (en) 2019-05-13 2023-11-28 Universal Display Corporation Organic electroluminescent materials and devices
US11634445B2 (en) 2019-05-21 2023-04-25 Universal Display Corporation Organic electroluminescent materials and devices
US11647667B2 (en) 2019-06-14 2023-05-09 Universal Display Corporation Organic electroluminescent compounds and organic light emitting devices using the same
US11920070B2 (en) 2019-07-12 2024-03-05 The University Of Southern California Luminescent janus-type, two-coordinated metal complexes
US11685754B2 (en) 2019-07-22 2023-06-27 Universal Display Corporation Heteroleptic organic electroluminescent materials
US11926638B2 (en) 2019-07-22 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US11708355B2 (en) 2019-08-01 2023-07-25 Universal Display Corporation Organic electroluminescent materials and devices
US11374181B2 (en) 2019-08-14 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11930699B2 (en) 2019-08-15 2024-03-12 Universal Display Corporation Organic electroluminescent materials and devices
US11925105B2 (en) 2019-08-26 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11937494B2 (en) 2019-08-28 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11600787B2 (en) 2019-08-30 2023-03-07 Universal Display Corporation Organic electroluminescent materials and devices
US11820783B2 (en) 2019-09-06 2023-11-21 Universal Display Corporation Organic electroluminescent materials and devices
US11864458B2 (en) 2019-10-08 2024-01-02 Universal Display Corporation Organic electroluminescent materials and devices
US11950493B2 (en) 2019-10-15 2024-04-02 Universal Display Corporation Organic electroluminescent materials and devices
US11697653B2 (en) 2019-10-21 2023-07-11 Universal Display Corporation Organic electroluminescent materials and devices
US11919914B2 (en) 2019-10-25 2024-03-05 Universal Display Corporation Organic electroluminescent materials and devices
US11765965B2 (en) 2019-10-30 2023-09-19 Universal Display Corporation Organic electroluminescent materials and devices
US11889708B2 (en) 2019-11-14 2024-01-30 Universal Display Corporation Organic electroluminescent materials and devices
US11778895B2 (en) 2020-01-13 2023-10-03 Universal Display Corporation Organic electroluminescent materials and devices
US11917900B2 (en) 2020-01-28 2024-02-27 Universal Display Corporation Organic electroluminescent materials and devices
US11932660B2 (en) 2020-01-29 2024-03-19 Universal Display Corporation Organic electroluminescent materials and devices
US11957047B2 (en) 2022-08-15 2024-04-09 Universal Display Corporation Organic electroluminescent materials and devices

Also Published As

Publication number Publication date
JPWO2005123873A1 (en) 2008-04-10
JP4894513B2 (en) 2012-03-14

Similar Documents

Publication Publication Date Title
JP4894513B2 (en) ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
JP4697142B2 (en) Organic electroluminescence element, display device and lighting device
JP4858169B2 (en) Organic electroluminescence device
JP5403105B2 (en) Organic electroluminescence element material and organic electroluminescence element
JP5076900B2 (en) Organic electroluminescence element, display device and lighting device
JP4952247B2 (en) ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
JP5454610B2 (en) White organic electroluminescence element, image display element, and illumination device
JP5040077B2 (en) Organic electroluminescence device
JP5076888B2 (en) ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
JPWO2005097940A1 (en) ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
WO2006103874A1 (en) Organic electroluminescent device material, organic electroluminescent device, display and illuminating device
WO2007029533A1 (en) Organic electroluminescence element, display device and illuminating device
JP2005314663A (en) Organic electroluminescent element material, organic electroluminescent element, display device and illuminating apparatus
JP4935001B2 (en) Organic electroluminescence element material
WO2005009088A1 (en) Organic electroluminescent device, illuminating device, and display
JP4904727B2 (en) ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
JPWO2006129471A1 (en) ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT MANUFACTURING METHOD, LIGHTING DEVICE, AND DISPLAY DEVICE
JP2007081014A (en) Organic electroluminescence element, display device, and lighting system
JPWO2005097941A1 (en) ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE
WO2006100925A1 (en) Material for organic el device, organic el device, display and illuminating device
JP5104981B2 (en) Organic electroluminescence element, display device and lighting device
WO2005062675A1 (en) Material for organic electroluminescent device, organic electroluminescent device, illuminating device and display
JP2005078996A (en) Organic electroluminescent element and display device
JP5760941B2 (en) Organic electroluminescence element, display device and lighting device

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KM KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2006514709

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

WWW Wipo information: withdrawn in national office

Country of ref document: DE

122 Ep: pct application non-entry in european phase