WO2006033563A1 - Organic light emitting device - Google Patents

Organic light emitting device Download PDF

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WO2006033563A1
WO2006033563A1 PCT/KR2005/003168 KR2005003168W WO2006033563A1 WO 2006033563 A1 WO2006033563 A1 WO 2006033563A1 KR 2005003168 W KR2005003168 W KR 2005003168W WO 2006033563 A1 WO2006033563 A1 WO 2006033563A1
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group
substituted
unsubstituted
formula
compound
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French (fr)
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Seok Hee Yoon
Jae Min Moon
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Lg Chem. Ltd.
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/14—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/06—Peri-condensed systems
    • H—ELECTRICITY
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    • 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
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • 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
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    • 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
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
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    • 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

Definitions

  • the present invention relates to a compound that is usable in an organic light emitting device and an organic light emitting device using the same.
  • An organic light emission phenomenon is an example of a conversion of current into visible rays through an internal process of a specific organic molecule.
  • the organic light emission phenomenon is based on the following mechanism.
  • organic material layers are interposed between an anode and a cathode, if voltage is applied between the two electrodes, electrons and holes respectively from the cathode and the anode are injected into the organic material layer.
  • the electrons and the holes which are injected into the organic material layer are recombined to form an exciton, and the exciton is reduced to a bottom state to emit light.
  • An organic light emitting device which is based on the above mechanism typically comprises a cathode, an anode, and organic material layer(s), for example, organic material layers including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, interposed between the anode and the cathode.
  • organic material layer(s) for example, organic material layers including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, interposed between the anode and the cathode.
  • the materials used in the organic light emitting device are mostly pure organic materials or complexes of organic material and metal.
  • the material used in the organic light emitting device may be classified as a hole injection material, a hole transport material, a light emitting material, an electron transport material, or an electron injection material, according to its use.
  • an organic material having a p-type property which is easily oxidized and is electrochemically stable when it is oxidized, is used as the hole injection material or the hole transport material.
  • an organic material having an n-type property which is easily reduced and is electrochemically stable when it is reduced, is used as the electron injection material or the electron transport material.
  • the light emitting layer material an organic material having both p-type and n-type properties is preferable, which is stable when it is oxidized and when it is reduced. Also a material having high light emission efficiency for conversion of the exciton into light when the exciton is formed is preferable.
  • the material used in the organic light emitting device further have the following properties.
  • the material used in the organic light emitting device have excellent thermal stability. It is because of joule heating produced as a result of a movement of charged particles in the organic light emitting device.
  • NPB which has recently been widely used as the hole transport layer material of the organic light emitting device, has a glass transition temperature of 100 0 C or lower, thus it is difficult to apply to an organic light emitting device requiring a high current.
  • the material used in the organic light emitting device must have excellent chemical stability, electric charge mobility, and interfacial characteristic with an electrode or an adjacent layer. That is to say, the material used in the organic light emitting device must be little deformed by moisture or oxygen. Furthermore, proper hole or electron mobility must be assured so as to balance density of the holes and that of the electrons in the light emitting layer of the organic light emitting device to maximize the formation of excitons. Additionally, it has to be able to have a good interface with an electrode including metal or metal oxides so as to assure stability of the device.
  • the present inventors have found an organic compound which is capable of satisfying conditions required of a material which can be used in an organic light emitting device, for example, a proper energy level, electrochemical stability, and thermal stability, and which has a chemical structure capable of playing various roles required in the organic light emitting device depending on a substituent group.
  • an object of the present invention is to provide the organic compound found by the present inventors, and an organic light emitting device using the organic compound.
  • Technical Solution [14] The present invention provides a novel compound represented by the following Formula 1, a compound of Formula 1 into which a thermosetting or photo- crosslinkable functional group is introduced, and an organic light emitting device.
  • the organic light emitting device comprises a first electrode, organic material layer(s) comprising a light emitting layer, and a second electrode, wherein the first electrode, the organic material layer(s), and the second electrode form a layered structure.
  • At least one layer of the organic material layer(s) includes a compound of Formula 1 or a compound of Formula 1 into which a thermosetting or photo-crosslinkable functional group is introduced:
  • ArI to Ar6 are each indepe substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or un ⁇ substituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group, and an acetylene group; or a heterocyclic group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a substituted or unsubstit
  • R3 and R4, and R7 and R8 each independently or collectively may be connected to form condensation rings or may form the condensation rings along with a group selected from the group consisting of O, S, NR, PR, CRR', and SiRR', wherein R and R' are each independently or collectively selected from the group consisting of hydrogen, oxygen, a substituted or unsubstituted alkyl group, a substituted or un- substituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, an amino group, a nitrile group, a nitro group, a halogen group, an amide group, and an ester group.
  • RI l and R 12 are each independently or collectively selected from the group consisting of an alkyl group; an alkoxy group; an aryl group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or un ⁇ substituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group, and an acetylene group; a heterocyclic group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group
  • the substituent group for the alkyl, alkenyl, alkoxy, aryl, and heterocyclic groups are a halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heterocyclic, nitrile, or acetylene group.
  • FIG. 1 illustrates an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4;
  • FIG. 2 illustrates an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron injection layer 8, and a cathode 4.
  • Y and Y' are each selected from the group consisting of hydrogen, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, an arylamine group, an aryl group, a heterocyclic group, a nitrile group, and an acetylene group, and may be connected to each other to form a condensation ring.
  • Illustrative, but non-limiting, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
  • Illustrative, but non-limiting, examples of the arylamine group include a diphenylamine group, a phetylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazolyl group, and a triphenylamine group.
  • Il ⁇ lustrative, but non-limiting, examples of the aryl group include a phenyl group, a naphthyl group, an anthranyl group, and a biphenyl group.
  • heterocyclic group examples include a pyridyl group, an acridyl group, a thiophenyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, and a quinolinyl group.
  • the alkyl group, the alkoxy group, and the alkenyl group of Rl to R12 of Formula 1 have a carbon number of 1 to 20.
  • Illustrative, but non-limiting, examples of the aryl group of Rl to R12 of Formula 1 are as follows. [34]
  • n of a thiophenyl group is 1 - 6; and R is an alkyl group, or a substituted or unsubstituted aryl group.
  • the halogen group of Rl to R12 of Formula 1 is exemplified by fluorine, chlorine, bromine, or iodine.
  • Z is selected from the group consisting of hydrogen, a C1-C20 alkyl group, a C1-C20 alkenyl group, a C1-C20 alkynyl group, an alkoxy group, an arylamine group, an aryl group, a heterocyclic group, a nitrile group, and an acetylene group.
  • Examples of the arylamine group, the aryl group, and the heterocyclic group of Z are as shown in the examples of the above-mentioned substituent groups of Rl to R12.
  • a compound preferable in the present invention is a compound in which X is C or Si, and R3 and R4 are hydrogen, or R3 and R4 are directly bonded to each other or form a condensation ring along with a group selected from the group consisting of O, S, NR, PR, CRR', and SiRR' in Formula 1 (wherein, R and R' are as defined in Formula 1).
  • Another compound preferable in the present invention is a compound in which X is C or Si, and R3 and R4, and R7 and R8 are each independently or collectively bonded, or form condensation rings along with groups selected from the group consisting of O, S, NR, PR, CRR', and SiRR' in Formula 1 (wherein, R and R' are as defined in Formula 1).
  • Still another compound preferable in the present invention is a compound represented by the following Formula 2.
  • the compound of Formula 1 has a core structure in which the basic frame of acridine is substituted with diarylamine and phenyl substituted with arylamine at a para-position thereof.
  • a plane constituting the acridine frame is perpendicular to another plane which include RI l and R 12, thus conjugation does not occur between the two above-mentioned planes. Due to the structural characteristic described above, the core structure of the compound of Formula 1 has limited conjugation.
  • the conjugation length of the compound has a close relationship with an energy band gap.
  • an energy band gap is reduced as a conjugation length of a compound increases.
  • the core structure since a conjugation structure is limited in the core structure of the compound of Formula 1, the core structure has a large energy band gap.
  • substituent groups which are frequently applied to hole injection layer materials, hole transport layer materials, light emitting layer materials, and electron transport layer materials which are used during the production of the organic light emitting device, are introduced into the core structure so as to produce substances capable of satisfying requirements of each organic material layer.
  • substituent groups which are frequently applied to hole injection layer materials, hole transport layer materials, light emitting layer materials, and electron transport layer materials which are used during the production of the organic light emitting device, are introduced into the core structure so as to produce substances capable of satisfying requirements of each organic material layer.
  • the core structure of the compound of Formula 1 includes the arylamine structure, it can have an energy level suitable for the hole injection and/or hole transport materials in the organic light emitting device.
  • the compound having the proper energy level is selected depending on the substituent group among the compounds expressed by Formula 1 to be used in the organic light emitting device, thereby it is possible to realize a device having low actuating voltage and high light efficiency.
  • the compounds of Formula 1-18 have HOMO of 5.24 eV, they have an energy level suitable for the hole injection layer or the hole transport layer. Meanwhile, the compounds of Formula 1-18 have the band gap of 3.3 eV, which is still larger than that of NPB, typically used as the hole transport layer material, thus they have a LUMO value of about 1.94 eV, which is very high. If a compound having a high LUMO value is used as the hole transport layer, it increases the energy wall of LUMO of the material constituting the light emitting layer to prevent the movement of electrons from the light emitting layer to the hole transport layer.
  • the above-mentioned compound improves the light emission efficiency of the organic light emitting device so that efficiency is higher than that of conventionally used NPB (HOMO 5.4 eV, LUMO 2.3 eV, and energy band gap 3.1 eV).
  • the energy band gap is calculated by a typical method using a UV-VIS spectrum.
  • the compound of Formula 1 has stable redox characteristics.
  • Redox stability is estimated using a CV (cyclovoltammetry) method. For example, if oxidation voltage is repeatedly applied to the compounds of Formula 1-18, oxidation repeatedly occurs at the same voltage and the current amount is the same. This means that the compound has excellent stability to oxidation.
  • the compound of Formula 1 since the compound of Formula 1 has a high glass transition temperature (Tg), it has excellent thermal stability.
  • Tg glass transition temperature
  • the glass transition temperature of the compound of Formula 1-18 is 12O 0 C, which is still higher than that of conventionally used NPB (Tg: 96 0 C).
  • the excellent thermal stability of the compound is an important factor providing actuating stability to the device.
  • the compound of Formula 1 may be used to form the organic material layer using a vacuum deposition process or a solution coating process during the production of the organic light emitting device.
  • a solution coating process include a spin coating process, a dip coating process, an inkjet printing process, a screen printing process, a spray process, and a roll coating process.
  • the compound of Formula 1-18 has excellent solubility to a polar solvent, such as xylene, dichloro ethane, or NMP, which is used during the production of the device, and forms a thin film very well through the process using a solution, thus the solution coating process may be applied to produce the device.
  • a light emitting wavelength of a thin film or a solid formed using the solution coating process is typically shifted to a longer wavelength due to interaction between molecules, in comparison with a light emitting wavelength in a solution state. However, less shift in the wavelength occurs in the compound having the structure shown in Formula 1.
  • a lithiated alkyl or aryl group is reacted with a carbonyl group of an ester group to produce tertiary alcohol, and the resulting alcohol is heated in the presence of an acid catalyst to form a hexagonal cyclic compound while water is removed, thereby producing the compound of Formula 1.
  • the above-mentioned procedure for producing the compound is well known in the art, and those skilled in the art can change the production conditions during the production of the compound of Formula 1. The production will be described in detail in the preparation examples as described later.
  • a compound, in which a thermosetting or photo-crosslinkable group is introduced into the compound of Formula 1 may be used instead of the compound of Formula 1.
  • This compound has the basic physical properties of the compound of Formula 1, and may be used to form a thin film using a solution coating process and then be cured so as to form an organic material layer during the production of the device.
  • thermosetting or photo-crosslinkable functional group may be a vinyl or an acryl group.
  • the organic light emitting device of the present invention can be produced using known materials through a known process, modified only in that at least one layer of organic material layer(s) include the compound of the present invention, the compound of Formula 1.
  • the organic material layer(s) of the organic light emitting device according to the present invention may have a single layer structure, or alternatively, a multi-layered structure in which two or more organic material layers are layered.
  • the organic light emitting device of the present invention may comprise a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer as the organic material layer.
  • the structure of the organic light emitting device is not limited to this, but may comprise a smaller number of organic material layers.
  • the organic light emitting device of the present invention may be produced, for example, by sequentially layering a first electrode, organic material layer(s), and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as a sputtering method or an e-beam evaporation method, may be used, but the method is not limited to these.
  • a glass substrate (corning 7059 glass), on which ITO (indium tin oxide) was applied to a thickness of 1000 A to form a thin film, was put in distilled water, in which a detergent was dissolved, and washed using ultrasonic waves.
  • a product manufactured by Fischer Inc. was used as the detergent, and distilled water was produced by filtering twice using a filter manufactured by Millipore Inc.
  • ultrasonic washing was conducted twice using distilled water for 10 min.
  • ultrasonic washing was conducted using isopropyl alcohol, acetone, and methanol solvents, and drying was then conducted. Next, it was transported to a plasma washing machine.
  • the substrate was dry washed using nitrogen plasma under a pressure of 14 mtorr at 85 W for 5 min, and then transported to a vacuum evaporator.
  • Hexanitrile hexaazatriphenylene (hereinafter, referred to as "HAT") of the following Formula was vacuum deposited to a thickness of 500 A by heating on a transparent ITO electrode, which was prepared through the above procedure, so as to form an anode including an ITO conductive layer and an n-type organic material.
  • the compound of Formula 1-18 (400 A) was vacuum deposited thereon to form hole injection and transport layers.
  • Alq3 was vacuum deposited to a thickness of 300 A on the hole transport layer to form a light emitting layer.
  • An electron transport layer material of the following Formula was deposited to a thickness of 200 A on the light emitting layer to form an electron transport layer.
  • Lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 2000 A were sequentially deposited on the electron transport layer to form a cathode.
  • the deposition speed of an organic material was maintained at 0.3 - 0.8 A/sec. Furthermore, lithium fluoride and aluminum were deposited at speeds of 0.3 A/sec and 1.5 - 2.5 A/sec, respectively, at the cathode. During the deposition, a vacuum was maintained at 1 ⁇ 3 x 10 . [193] The resulting device had an electric field of 8.14 V at a forward current density of
  • the operation and light emission of the device at the above-mentioned actuating voltage mean that the compound of Formula 1-18 which formed the layer between the hole injection layer and the light emitting layer functions to transport holes.
  • HAT was deposited to a thickness of 80 A on an ITO substrate, which was prepared through the same procedure as example 1, so as to form an anode including an ITO conductive layer and an n-type organic material. Subsequently, the compound of
  • Formula 1-18 was deposited to a thickness of 800 A on the anode to form a hole injection layer.
  • NPB was deposited to a thickness of 300 A on the hole injection layer to form a hole transport layer
  • Alq3 was deposited to a thickness of 300 A thereon to form a light emitting layer.
  • An electron transport layer and a cathode were formed on the light emitting layer through the same procedure as in example 1.
  • the resulting device had an electric field of 9.94 V at a forward current density of
  • the operation and light emission of the device at the above-mentioned actuating voltage mean that the compound of Formula 1-18 forming the layer between the thin film formed on the substrate and the hole transport layer functions to inject holes.
  • the compound of the present invention can be used as an organic material layer material, particularly, hole injection and/or transport materials in an organic light emitting device, and when applied to an organic light emitting device it is possible to reduce the actuating voltage of the device, to improve the light efficiency thereof, and to improve the lifespan of the device through the thermal stability of the compound.

Abstract

Disclosed is a compound of Formula 1, and an organic light emitting device comprising the compound of Formula 1 or the compound of Formula 1 into which a thermosetting or photo- crosslinkable functional group is introduced.

Description

Description
ORGANIC LIGHT EMITTING DEVICE
Technical Field
[1] The present invention relates to a compound that is usable in an organic light emitting device and an organic light emitting device using the same.
[2]
Background Art
[3] An organic light emission phenomenon is an example of a conversion of current into visible rays through an internal process of a specific organic molecule. The organic light emission phenomenon is based on the following mechanism. When organic material layers are interposed between an anode and a cathode, if voltage is applied between the two electrodes, electrons and holes respectively from the cathode and the anode are injected into the organic material layer. The electrons and the holes which are injected into the organic material layer are recombined to form an exciton, and the exciton is reduced to a bottom state to emit light. An organic light emitting device which is based on the above mechanism typically comprises a cathode, an anode, and organic material layer(s), for example, organic material layers including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, interposed between the anode and the cathode.
[4] The materials used in the organic light emitting device are mostly pure organic materials or complexes of organic material and metal. The material used in the organic light emitting device may be classified as a hole injection material, a hole transport material, a light emitting material, an electron transport material, or an electron injection material, according to its use. In connection with this, an organic material having a p-type property, which is easily oxidized and is electrochemically stable when it is oxidized, is used as the hole injection material or the hole transport material. Meanwhile, an organic material having an n-type property, which is easily reduced and is electrochemically stable when it is reduced, is used as the electron injection material or the electron transport material. As the light emitting layer material, an organic material having both p-type and n-type properties is preferable, which is stable when it is oxidized and when it is reduced. Also a material having high light emission efficiency for conversion of the exciton into light when the exciton is formed is preferable.
[5] In addition, it is preferable that the material used in the organic light emitting device further have the following properties.
[6] First, it is preferable that the material used in the organic light emitting device have excellent thermal stability. It is because of joule heating produced as a result of a movement of charged particles in the organic light emitting device. NPB, which has recently been widely used as the hole transport layer material of the organic light emitting device, has a glass transition temperature of 1000C or lower, thus it is difficult to apply to an organic light emitting device requiring a high current.
[7] Second, in order to produce an organic light emitting device that is capable of being actuated at low voltage and has high efficiency, holes and electrons which are injected into the organic light emitting device must be smoothly transported to a light emitting layer, and must not be released out of the light emitting layer. To achieve this, a material used in the organic light emitting device must have a proper band gap and a proper HOMO or LUMO energy levels. The LUMO energy level of PEDOT:PSS, which is currently used as a hole transport material of an organic light emitting device produced using a solution coating method, is lower than that of an organic material used as a light emitting layer material, thus it is difficult to produce an organic light emitting device having high efficiency and a long lifespan.
[8] Moreover, the material used in the organic light emitting device must have excellent chemical stability, electric charge mobility, and interfacial characteristic with an electrode or an adjacent layer. That is to say, the material used in the organic light emitting device must be little deformed by moisture or oxygen. Furthermore, proper hole or electron mobility must be assured so as to balance density of the holes and that of the electrons in the light emitting layer of the organic light emitting device to maximize the formation of excitons. Additionally, it has to be able to have a good interface with an electrode including metal or metal oxides so as to assure stability of the device.
[9] There is a need to develop an organic material having the above-mentioned re¬ quirements in the art.
[10]
Disclosure of Invention Technical Problem
[11] The present inventors have found an organic compound which is capable of satisfying conditions required of a material which can be used in an organic light emitting device, for example, a proper energy level, electrochemical stability, and thermal stability, and which has a chemical structure capable of playing various roles required in the organic light emitting device depending on a substituent group.
[12] Accordingly, an object of the present invention is to provide the organic compound found by the present inventors, and an organic light emitting device using the organic compound. Technical Solution [14] The present invention provides a novel compound represented by the following Formula 1, a compound of Formula 1 into which a thermosetting or photo- crosslinkable functional group is introduced, and an organic light emitting device. The organic light emitting device comprises a first electrode, organic material layer(s) comprising a light emitting layer, and a second electrode, wherein the first electrode, the organic material layer(s), and the second electrode form a layered structure. At least one layer of the organic material layer(s) includes a compound of Formula 1 or a compound of Formula 1 into which a thermosetting or photo-crosslinkable functional group is introduced:
[15] [Formula 1]
[16]
Figure imgf000004_0001
[17] In Formula 1 , X is C or Si,
[18] ArI to Ar6 are each indepe substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or un¬ substituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group, and an acetylene group; or a heterocyclic group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a substituted or unsubstituted arylamine group, an aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group, and an acetylene group, and which includes O, N, or S as a heteroatom, and the ArI to Ar6 may form aliphatic or hetero condensation rings along with adjacent groups; [19] Rl to RlO are each independently or collectively selected from the group consisting of a hydrogen atom; an alkyl group; an alkoxy group; a thioalkoxy group, an acetylene group; an alkenyl group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitro group, a nitrile group, and an acetylene group; an alkynyl group, which is substituted or un¬ substituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or un¬ substituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitro group, a nitrile group, and an acetylene group; an aryl group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitro group, a nitrile group, and an acetylene group; an arylamine group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted het¬ erocyclic group, a nitro group, a nitrile group, and an acetylene group; a heterocyclic group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or un¬ substituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitro group, a nitrile group, and an acetylene group, and which includes O, N, or S as a heteroatom; an amino group, which is substituted with at least one substituent group selected from the group consisting of an alkyl group, an alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, and a substituted or unsubstituted arylalkenyl group; a nitrile group; a nitro group; a halogen group; an amide group; an imide group; and an ester group, and Rl to RlO may form aliphatic or condensation rings along with adjacent groups.
[20] R3 and R4, and R7 and R8 each independently or collectively may be connected to form condensation rings or may form the condensation rings along with a group selected from the group consisting of O, S, NR, PR, CRR', and SiRR', wherein R and R' are each independently or collectively selected from the group consisting of hydrogen, oxygen, a substituted or unsubstituted alkyl group, a substituted or un- substituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, an amino group, a nitrile group, a nitro group, a halogen group, an amide group, and an ester group.
[21] RI l and R 12 are each independently or collectively selected from the group consisting of an alkyl group; an alkoxy group; an aryl group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or un¬ substituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group, and an acetylene group; a heterocyclic group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, and an acetylene group, and which includes O, N, or S as a heteroatom; a nitrile group; an amide group; an imide group; and an ester group.
[22] In connection with this, the substituent group for the alkyl, alkenyl, alkoxy, aryl, and heterocyclic groups are a halogen, alkyl, alkenyl, alkoxy, arylamine, aryl, arylalkyl, arylalkenyl, heterocyclic, nitrile, or acetylene group.
[23]
Brief Description of the Drawings
[24] FIG. 1 illustrates an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4; and
[25] FIG. 2 illustrates an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron injection layer 8, and a cathode 4.
[26] Best Mode for Carrying Out the Invention
[27] A detailed description will be given of substituent groups of Formula 1. [28] Illustrative, but non-limiting, examples of ArI to Ar6 of Formula 1 include groups as shown in the following Formulae.
[29]
Figure imgf000007_0001
Figure imgf000007_0002
Figure imgf000007_0003
Figure imgf000007_0004
[30] In the above Formulae, Y and Y' are each selected from the group consisting of hydrogen, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, an arylamine group, an aryl group, a heterocyclic group, a nitrile group, and an acetylene group, and may be connected to each other to form a condensation ring.
[31] Illustrative, but non-limiting, examples of the halogen group include fluorine, chlorine, bromine, and iodine. Illustrative, but non-limiting, examples of the arylamine group include a diphenylamine group, a phetylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazolyl group, and a triphenylamine group. Il¬ lustrative, but non-limiting, examples of the aryl group include a phenyl group, a naphthyl group, an anthranyl group, and a biphenyl group. Illustrative, but non- limiting, examples of the heterocyclic group include a pyridyl group, an acridyl group, a thiophenyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, and a quinolinyl group.
[32] It is preferable that the alkyl group, the alkoxy group, and the alkenyl group of Rl to R12 of Formula 1 have a carbon number of 1 to 20. [33] Illustrative, but non-limiting, examples of the aryl group of Rl to R12 of Formula 1 are as follows. [34]
O
Figure imgf000008_0001
Figure imgf000008_0002
Figure imgf000008_0003
Figure imgf000008_0004
Figure imgf000008_0005
Figure imgf000008_0006
Figure imgf000008_0007
Figure imgf000008_0008
Figure imgf000009_0001
[35] Illustrative, but non-limiting, examples of the arylamine group of Rl to R12 of Formula 1 are as follows. [36]
Figure imgf000009_0002
Figure imgf000009_0003
Figure imgf000009_0004
[37] Illustrative, but non-limiting, examples of the heterocyclic group of Rl to R 12 of Formula 1 are as follows. [38]
*Hζ J
~tθ
Figure imgf000010_0001
Figure imgf000010_0002
Figure imgf000010_0003
=ø>
Figure imgf000010_0004
■ <>
Figure imgf000010_0005
[39] [40] In the above substituent groups: n of a thiophenyl group is 1 - 6; and R is an alkyl group, or a substituted or unsubstituted aryl group.
[41] Illustrative, but non-limiting, examples of the arylalkenyl group of Rl to R12 of Formula 1 are as follows. [42]
Figure imgf000010_0006
Figure imgf000011_0001
[43] The halogen group of Rl to R12 of Formula 1 is exemplified by fluorine, chlorine, bromine, or iodine. [44] In the above Formulae, Z is selected from the group consisting of hydrogen, a C1-C20 alkyl group, a C1-C20 alkenyl group, a C1-C20 alkynyl group, an alkoxy group, an arylamine group, an aryl group, a heterocyclic group, a nitrile group, and an acetylene group. Examples of the arylamine group, the aryl group, and the heterocyclic group of Z are as shown in the examples of the above-mentioned substituent groups of Rl to R12.
[45] A compound preferable in the present invention is a compound in which X is C or Si, and R3 and R4 are hydrogen, or R3 and R4 are directly bonded to each other or form a condensation ring along with a group selected from the group consisting of O, S, NR, PR, CRR', and SiRR' in Formula 1 (wherein, R and R' are as defined in Formula 1).
[46] Another compound preferable in the present invention is a compound in which X is C or Si, and R3 and R4, and R7 and R8 are each independently or collectively bonded, or form condensation rings along with groups selected from the group consisting of O, S, NR, PR, CRR', and SiRR' in Formula 1 (wherein, R and R' are as defined in Formula 1).
[47] In an embodiment of the present invention, CRR' may be a ketone group (C(=O)). [48] Still another compound preferable in the present invention is a compound represented by the following Formula 2.
[49] [Formula 2] [50]
Figure imgf000011_0002
[51] In the above Formula, ArI to Ar6, RI l and R12 are as defined in Formula 1. [52] Yet another compound useful in the present invention is a compound represented by the following Formula 3.
[53] Formula 3 [54]
Figure imgf000012_0001
[55] In the above Formula, ArI to Ar6, RI l and R12 are as defined in Formula 1. [56] Illustrative, but non-limiting, examples of a compound of Formula 1 include compounds shown in the following Formulae.
[57] [58] Formula 1-1 Formula 1-2 [59]
Figure imgf000012_0002
[60] [61] Formula 1-3 Formula 1-4 [62]
Figure imgf000013_0001
[63] [64] Foraiula 1-5 Formula 1-6 [65]
Figure imgf000013_0002
[66] [67] Formula 1-7 Formula 1-8 [68]
Figure imgf000014_0001
[69] [70] Formula 1-9 Formula 1-10 [71]
Figure imgf000014_0002
[72] Formula 1-11 Formula 1-12 [73]
Figure imgf000015_0001
[74] [75] Formula 1-13 Formula 1-14 [76]
Figure imgf000015_0002
[77] [78] Formula 1-15 Formula 1-16 [79]
Figure imgf000016_0001
[80] [81] Formula 1-17 Formula 1-18 [82]
Figure imgf000016_0002
Figure imgf000017_0001
[83] [84] Formula 1-19 Formula 1-20 [85]
Figure imgf000017_0002
[86] [87] Formula 1-21 Formula 1-22 [88]
Figure imgf000018_0001
[89] [90] Formula 1-23 Formula 1-24 [91]
Figure imgf000018_0002
[92] [93] Formula 1-25 Formula 1-26 [94]
Figure imgf000019_0001
Figure imgf000019_0004
Figure imgf000019_0002
[95] [96] Formula 1-27 [97]
Figure imgf000019_0003
[98] [99] Formula 1-28 [100]
Figure imgf000020_0001
[101]
[102] In a core structure of the compound of Formula 1, the basic frame of acridine is substituted with diarylamine and phenyl substituted with diarylamine. Various substituent groups are introduced into the above basic structure to assure charac¬ teristics suitable to be used for an organic material layer of an organic light emitting device. This will be described in detail, below.
[103] The compound of Formula 1 has a core structure in which the basic frame of acridine is substituted with diarylamine and phenyl substituted with arylamine at a para-position thereof. In this structure, since a carbon atom or a silicon atom con¬ stituting X has an sp bond, a plane constituting the acridine frame is perpendicular to another plane which include RI l and R 12, thus conjugation does not occur between the two above-mentioned planes. Due to the structural characteristic described above, the core structure of the compound of Formula 1 has limited conjugation.
[104] The conjugation length of the compound has a close relationship with an energy band gap. In detail, an energy band gap is reduced as a conjugation length of a compound increases. As described above, since a conjugation structure is limited in the core structure of the compound of Formula 1, the core structure has a large energy band gap.
[105] As described above, in the present invention, various substituent groups are introduced into Rl - R12 positions and ArI - Ar6 positions of the core structure having the large energy band gap so as to produce compounds having various energy band gaps. Generally, it is easy to control the energy band gap by introducing the substituent groups into the core structure having a large energy band gap, but it is difficult to sig¬ nificantly control the energy band gap by introducing the substituent groups into the core structure having a small energy band gap. Furthermore, in the present invention, it is possible to control HOMO and LUMO energy levels of the compound by in¬ troducing various substituent groups into Rl - R12 and ArI - Ar6 of the core structure.
[106] Additionally, by introducing various substituent groups into the core structure, compounds having intrinsic characteristics of the substituent groups can be synthesized. For example, substituent groups, which are frequently applied to hole injection layer materials, hole transport layer materials, light emitting layer materials, and electron transport layer materials which are used during the production of the organic light emitting device, are introduced into the core structure so as to produce substances capable of satisfying requirements of each organic material layer. Par¬ ticularly, since the core structure of the compound of Formula 1 includes the arylamine structure, it can have an energy level suitable for the hole injection and/or hole transport materials in the organic light emitting device. In the present invention, the compound having the proper energy level is selected depending on the substituent group among the compounds expressed by Formula 1 to be used in the organic light emitting device, thereby it is possible to realize a device having low actuating voltage and high light efficiency.
[107] With respect to the energy band gap and the energy level, for example, since the compounds of Formula 1-18 have HOMO of 5.24 eV, they have an energy level suitable for the hole injection layer or the hole transport layer. Meanwhile, the compounds of Formula 1-18 have the band gap of 3.3 eV, which is still larger than that of NPB, typically used as the hole transport layer material, thus they have a LUMO value of about 1.94 eV, which is very high. If a compound having a high LUMO value is used as the hole transport layer, it increases the energy wall of LUMO of the material constituting the light emitting layer to prevent the movement of electrons from the light emitting layer to the hole transport layer. Accordingly, the above-mentioned compound improves the light emission efficiency of the organic light emitting device so that efficiency is higher than that of conventionally used NPB (HOMO 5.4 eV, LUMO 2.3 eV, and energy band gap 3.1 eV). In the present invention, the energy band gap is calculated by a typical method using a UV-VIS spectrum.
[108] In addition, the compound of Formula 1 has stable redox characteristics. Redox stability is estimated using a CV (cyclovoltammetry) method. For example, if oxidation voltage is repeatedly applied to the compounds of Formula 1-18, oxidation repeatedly occurs at the same voltage and the current amount is the same. This means that the compound has excellent stability to oxidation.
[109] Meanwhile, since the compound of Formula 1 has a high glass transition temperature (Tg), it has excellent thermal stability. For example, the glass transition temperature of the compound of Formula 1-18 is 12O0C, which is still higher than that of conventionally used NPB (Tg: 960C). The excellent thermal stability of the compound is an important factor providing actuating stability to the device.
[110] Furthermore, the compound of Formula 1 may be used to form the organic material layer using a vacuum deposition process or a solution coating process during the production of the organic light emitting device. In connection with this, illustrative, but non-limiting examples of the solution coating process include a spin coating process, a dip coating process, an inkjet printing process, a screen printing process, a spray process, and a roll coating process.
[I l l] For example, the compound of Formula 1-18 has excellent solubility to a polar solvent, such as xylene, dichloro ethane, or NMP, which is used during the production of the device, and forms a thin film very well through the process using a solution, thus the solution coating process may be applied to produce the device. Additionally, a light emitting wavelength of a thin film or a solid formed using the solution coating process is typically shifted to a longer wavelength due to interaction between molecules, in comparison with a light emitting wavelength in a solution state. However, less shift in the wavelength occurs in the compound having the structure shown in Formula 1.
[112] A lithiated alkyl or aryl group is reacted with a carbonyl group of an ester group to produce tertiary alcohol, and the resulting alcohol is heated in the presence of an acid catalyst to form a hexagonal cyclic compound while water is removed, thereby producing the compound of Formula 1. The above-mentioned procedure for producing the compound is well known in the art, and those skilled in the art can change the production conditions during the production of the compound of Formula 1. The production will be described in detail in the preparation examples as described later.
[113] In the organic light emitting device of the present invention, a compound, in which a thermosetting or photo-crosslinkable group is introduced into the compound of Formula 1, may be used instead of the compound of Formula 1. This compound has the basic physical properties of the compound of Formula 1, and may be used to form a thin film using a solution coating process and then be cured so as to form an organic material layer during the production of the device.
[114] The method of forming the organic material layer, which comprises introducing the curable functional group into the organic material during the production of the organic light emitting device, forming the organic thin film using the solution coating process, and curing the resulting film, is disclosed in US Pat. No. 2003-0044518 and EP Pat. No. 1146574 A2.
[115] The above documents state that, if the organic material layer is formed through the above-mentioned method using a material having a thermosetting or photo- crosslinkable vinyl or acryl group so as to produce the organic light emitting device, it is possible to produce an organic light emitting device having low voltage and high brightness as well as an organic light emitting device having a multilayered structure using the solution coating process. This operation mechanism may be applied to the compound of the present invention.
[116] In the present invention, the thermosetting or photo-crosslinkable functional group may be a vinyl or an acryl group.
[117] The organic light emitting device of the present invention can be produced using known materials through a known process, modified only in that at least one layer of organic material layer(s) include the compound of the present invention, the compound of Formula 1.
[118] The organic material layer(s) of the organic light emitting device according to the present invention may have a single layer structure, or alternatively, a multi-layered structure in which two or more organic material layers are layered. For example, the organic light emitting device of the present invention may comprise a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer as the organic material layer. However, the structure of the organic light emitting device is not limited to this, but may comprise a smaller number of organic material layers.
[119] Furthermore, the organic light emitting device of the present invention may be produced, for example, by sequentially layering a first electrode, organic material layer(s), and a second electrode on a substrate. In connection with this, a physical vapor deposition (PVD) method, such as a sputtering method or an e-beam evaporation method, may be used, but the method is not limited to these.
[120]
Mode for the Invention
[121] A better understanding of a method of producing the compound of Formula 1 and the production of an organic light emitting device using the same according to the present invention may be obtained in light of the following preparation examples and examples which are set forth to illustrate, but are not to be construed to limit the present invention.
[122]
[123] PREPARATION EXAMPLE 1
[124]
[125] Production of compound 1-18
[126]
Figure imgf000024_0001
Nrtrobβns&ne
Figure imgf000024_0002
Figure imgf000024_0003
Figure imgf000024_0004
[127] Production of compound A [128] 16.9 g of diphenylamine, 16.7 rnL of 2-iodo-methyl benzoate, 15.2 g of potassium carbonate, 7.0 g of copper powder, and 15.6 g of sodium sulfate were added to 50 mL of nitrobenzene and stirred at 190 - 2000C for one day. After the mixture was cooled to normal temperature, THF was added thereto to dissolve it, and filtering was conducted. The solvent was removed from the filtered solution, ethanol was added to the resulting mixture, and stirring was conducted. After the solid obtained through the filtration was dissolved in THF and passed through a silica gel, the solvent was removed therefrom, and stirring was conducted in acetone. Crystallization was carried out to produce a solid, and the solid was filtered to create 22.4 g of a product.
[129] [130] Production of compound B [131] 18.2 g of compound A were dissolved in 150 mL of purified THF and cooled to O0C, and a 1.6 M methyl lithium solution which was dispersed in ethyl ether was slowly added thereto. The resulting reactants were slowly heated to room temperature and stirred for one day. The reaction was completed with water. Subsequently, the resulting material was extracted with ethyl ether, remaining moisture was removed from an organic material layer, and an organic solvent was removed, n-hexane was added to the resulting yellow liquid, and the resulting solution was boiled with stirring, cooled to normal temperature, and filtered. The solid obtained through the filtration was washed with n-hexane and vacuum dried to create 11.86 g of product.
[132] After 100 mL of acetic acid and 0.5 mL of concentrated hydrochloric acid were added to 11.86 g of product, boiling with stirring were carried out for 40 min. The resulting substance was cooled to normal temperature, the acetic acid was removed at a reduced pressure, ethanol was added thereto, and stirring was conducted. The resulting solid was filtered to create 9.5 g of white product.
[133] NMR (CDCl ): 7.67 - 7.63 ( t, 2H ), 7.55 - 7.51 ( t, IH ), 7.49 - 7.47 ( d, 2H ), 7.38 -
7.35 ( d, 2H ), 7.01 - 6.92 ( t, t, 4H ), 6.30 - 6.28 ( d, 2H ), 1.72 ( s, 6H )
[134] MS : [M+H]+=286
[135] HOMO : 5.8O eV
[136] Band gap : 3.7 eV
[137] LUMO : 2.1O eV
[138]
[139] Production of compound C
[140] 8.56 g of compound B were dissolved in 300 mL of chloroform, and 4.67 mL of bromine were slowly added thereto. The resulting reactants was stirred for 2 hours. Water and a small amount of acetone were added thereto to complete the reaction, and a water layer and an organic material layer were separated from each other. After water was removed from the organic material layer, the resulting substance was passed through a silica gel using chloroform, and an organic solvent was removed and ethanol was added thereto to conduct solidification, thereby 12.28 g of white solid were produced.
[141] NMR (CDCl ) : 7.79 - 7.75 ( d, 2H ), 7.52 - 7.50 ( s, 2H ), 7.20 -7.15 ( d, 2H ), 7.09
- 7.04 ( d, 2H ), 6.14 - 6.10 ( d, 2H ), 1.63 ( s, 6H )
[142]
[143] Production of compound 1-18
[144] After 1.044 g of compound C and 1.117 g of diphenylamine were dissolved in 10 mL of xylene, 0.769 g of sodium-t-butoxide, 0.110 g of tris(dibenzylideneacetone)dipalladium(0), and 0.036 g of tri-tert-butyl phosphine were sequentially added thereto, and they were boiled for 4 hours with stirring. The resulting reactants were cooled to normal temperature, the reaction was completed with water, and extraction was conducted using xylene. Water was removed from the organic material layer using anhydrous magnesium sulfate, and then an organic solvent was removed, and the resulting solution was subjected to a column separation process in a ratio of tetrahydrofuran/n-hexane of 1/19 to create 1.26 g of product.
[145] MS : [M+H]+=787
[146] HOMO : 5.24
[147] Band gap = 3.3 eV
[148] LUMO : 1.94 eV
[149] Tg : 120 0C
[150]
[151] PREPARATION EXAMPLE 2
[152]
[153] Production of compound 1-14
[154] The procedure of preparation example 1 was repeated with the exception that diphenylamine was substituted with carbazole during the production of the in¬ termediate A.
[155]
[156] PREPARATION EXAMPLE 3
[157]
[158] Production of compound 1-21
[159] The procedure of preparation example 1 was repeated with the exception that phenyl lithium was used instead of methyl lithium during the production of the in¬ termediate B.
[160]
[161] PREPARATION EXAMPLE 4
[162]
[163] Production of compound 1-23
[164] The procedure of preparation example 1 was repeated with the exception that diphenylamine was substituted with carbazole during the production of the in¬ termediate A and that phenyl- 1-naphthylamine was used instead of substituting diphenylamine in the final compound.
[165]
[166] PREPARATION EXAMPLE 5
[167]
[168] Production of compound 1-24
[169] The procedure of preparation example 1 was repeated with the exception that carbazole was used instead of diphenylamine during the production of the final compound.
[170]
[171] PREPARATION EXAMPLE 6
[172] [173] Production of compound 1-26
[174] The procedure of preparation example 4 was repeated with the exception that carbazole was used instead of phenyl- 1-naphthylamine during the production of the final compound.
[175]
[176] PREPARATION EXAMPLE 7
[177]
[178] Production of compound 1-20
[179] The procedure of preparation example 4 was repeated with the exception that phenoxazine was used instead of carbazole during the production of the intermediate A.
[180]
[181] [Production of an organic light emitting device]
[182] EXAMPLE 1
[183] A glass substrate (corning 7059 glass), on which ITO (indium tin oxide) was applied to a thickness of 1000 A to form a thin film, was put in distilled water, in which a detergent was dissolved, and washed using ultrasonic waves. In connection with this, a product manufactured by Fischer Inc. was used as the detergent, and distilled water was produced by filtering twice using a filter manufactured by Millipore Inc. After ITO was washed for 30 min, ultrasonic washing was conducted twice using distilled water for 10 min. After the washing using distilled water was completed, ultrasonic washing was conducted using isopropyl alcohol, acetone, and methanol solvents, and drying was then conducted. Next, it was transported to a plasma washing machine. The substrate was dry washed using nitrogen plasma under a pressure of 14 mtorr at 85 W for 5 min, and then transported to a vacuum evaporator.
[184] Hexanitrile hexaazatriphenylene (hereinafter, referred to as "HAT") of the following Formula was vacuum deposited to a thickness of 500 A by heating on a transparent ITO electrode, which was prepared through the above procedure, so as to form an anode including an ITO conductive layer and an n-type organic material.
[185] [HAT]
[186]
C N
C N
N
N C N N
N f
N
[ C N
C N
[187] The compound of Formula 1-18 (400 A) was vacuum deposited thereon to form hole injection and transport layers. Alq3 was vacuum deposited to a thickness of 300 A on the hole transport layer to form a light emitting layer. An electron transport layer material of the following Formula was deposited to a thickness of 200 A on the light emitting layer to form an electron transport layer. [188]
[ 189] [Electron transport layer material]
[190]
Figure imgf000028_0001
[191] Lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 2000 A were sequentially deposited on the electron transport layer to form a cathode.
[192] In the above procedure, the deposition speed of an organic material was maintained at 0.3 - 0.8 A/sec. Furthermore, lithium fluoride and aluminum were deposited at speeds of 0.3 A/sec and 1.5 - 2.5 A/sec, respectively, at the cathode. During the deposition, a vacuum was maintained at 1 ~ 3 x 10 . [193] The resulting device had an electric field of 8.14 V at a forward current density of
100 mA/cm , and emitted green light at a light efficiency of 0.53 lm/W. [194] The operation and light emission of the device at the above-mentioned actuating voltage mean that the compound of Formula 1-18 which formed the layer between the hole injection layer and the light emitting layer functions to transport holes. [195]
[196] EXAMPLE 2
[197] [198] HAT was deposited to a thickness of 80 A on an ITO substrate, which was prepared through the same procedure as example 1, so as to form an anode including an ITO conductive layer and an n-type organic material. Subsequently, the compound of
Formula 1-18 was deposited to a thickness of 800 A on the anode to form a hole injection layer.
[199] NPB was deposited to a thickness of 300 A on the hole injection layer to form a hole transport layer, and Alq3 was deposited to a thickness of 300 A thereon to form a light emitting layer. An electron transport layer and a cathode were formed on the light emitting layer through the same procedure as in example 1.
[200] In the present example, deposition speeds of the organic material and the cathode, and a vacuum during the deposition were the same as those of example 1.
[201] The resulting device had an electric field of 9.94 V at a forward current density of
100 mA/cm , and emitted green light at a light efficiency of 1.44 lm/W.
[202] The operation and light emission of the device at the above-mentioned actuating voltage mean that the compound of Formula 1-18 forming the layer between the thin film formed on the substrate and the hole transport layer functions to inject holes.
[203]
Industrial Applicability
[204] The compound of the present invention can be used as an organic material layer material, particularly, hole injection and/or transport materials in an organic light emitting device, and when applied to an organic light emitting device it is possible to reduce the actuating voltage of the device, to improve the light efficiency thereof, and to improve the lifespan of the device through the thermal stability of the compound.

Claims

Claims
[1] A compound expressed by Formula 1: [Formula 1]
Figure imgf000030_0001
wherein X is C or Si;
ArI to Ar6 independently or collectively are an aryl group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or un¬ substituted heterocyclic group, a nitrile group, a nitro group, and an acetylene group; or a heterocyclic group, which is substituted or unsubstituted with at least one substituent groups selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a substituted or unsubstituted arylamine group, an aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group, and an acetylene group, and which includes O, N, or S as a heteroatom, and the ArI to Ar6 may form aliphatic or hetero condensation rings along with adjacent groups; Rl to RlO are each independently or collectively selected from the group consisting of a hydrogen atom; an alkyl group having a carbon number of 1 - 20; an alkoxy group having a carbon number of 1 - 20; a thioalkoxy group, an acetylene group; an alkenyl group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted het- erocyclic group, a nitrile group, a nitro group and an acetylene group; an aryl group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group and an acetylene group; an arylamine group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or un¬ substituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group and an acetylene group; a heterocyclic group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a thioalkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or un¬ substituted heterocyclic group, a nitrile group, a nitro group and an acetylene group, and which includes O, N, or S as a heteroatom; an amino group, which is substituted with at least one substituent group selected from the group consisting of an alkyl group, an alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylalkyl group, and a substituted or unsubstituted arylalkenyl group; a nitrile group; a nitro group; a halogen group; an amide group; an imide group; and an ester group, the Rl to RlO may form aliphatic or hetero condensation rings along with adjacent groups;
R3 and R4, and R7 and R8 each independently or collectively may be connected to form condensation rings or may form the condensation rings along with a group selected from the group consisting of O, S, NR, PR, CRR', and SiRR', wherein R and R' are each independently or collectively selected from the group consisting of hydrogen, oxygen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heterocyclic group, an amino group, a nitrile group, a nitro group, a halogen group, an amide group, and an ester group; and RI l and R12 are each independently or collectively selected from the group consisting of an alkyl group having 1 to 20 carbon atoms; an alkoxy group having 1 to 20 carbon atoms; an aryl group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or un¬ substituted aryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted het¬ erocyclic group, a nitrile group, a nitro group and an acetylene group; a het¬ erocyclic group, which is substituted or unsubstituted with at least one substituent group selected from the group consisting of a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, a substituted or un¬ substituted arylalkyl group, a substituted or unsubstituted arylalkenyl group, a substituted or unsubstituted heterocyclic group, a nitrile group, a nitro group and an acetylene group, and which includes O, N, or S as a heteroatom; a nitrile group; a nitro group; an amide group; an imide group and an ester group.
[2] The compound as set forth in claim 1, wherein ArI to Ar6 of Formula 1 are each independently or collectively selected from the group consisting of groups represented by the following Formulae:
Figure imgf000032_0001
in the above Formulae, Y and Y' are each selected from the group consisting of hydrogen, a halogen group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an arylamine group, an aryl group, a heterocyclic group, a nitrile group, and an acetylene group, and may be connected to each other to form a condensation ring. [3] The compound as set forth in claim 1, wherein, in Formula 1, X is C or Si; and R3 and R4 and/or R7 and R8 are each independently or collectively directly connected to form condensation rings, or form condensation rings along with groups selected from the group consisting of O, S, NR, PR, CRR', and SiRR' (R and R' being as defined in Formula 1).
[4] The compound as set forth in claim 1, wherein the compound of Formula 1 is represented by Formula 2 or 3:
[Formula 2]
Figure imgf000033_0001
[Formula 3]
Figure imgf000033_0002
in Formulae 2 and 3, ArI to Ar6, Rl 1, and R12 are as defined in Formula 1.
[5] The compound as set forth in claim 1, wherein a thermosetting or photo- crosslinkable functional group is introduced into the compound of Formula 1. [6] An organic light emitting device, comprising: a first electrode; organic material layer(s) comprising a light emitting layer, wherein at least one layer of the organic material layer(s) includes the compound according to any one of claims 1 to 5; and a second electrode; wherein the first electrode, the organic material layer(s), and the second electrode form layered structure.
[7] The organic light emitting device as set forth in claim 6, wherein the organic material layer(s) comprise a hole transport layer, the hole transport layer including the compound according to any one of claims 1 to 5.
[8] The organic light emitting device as set forth in claim 6, wherein the organic material layer(s) comprise a hole injection layer, the hole injection layer including the compound according to any one of claims 1 to 5.
[9] The organic light emitting device as set forth in claim 6, wherein the organic material layer(s) comprise a layer which both injects and transports holes and which includes the compound according to any one of claims 1 to 5.
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