WO2013154325A1 - Novel organic electroluminescent compounds and organic electroluminescent device containing the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device containing the same Download PDF

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WO2013154325A1
WO2013154325A1 PCT/KR2013/002954 KR2013002954W WO2013154325A1 WO 2013154325 A1 WO2013154325 A1 WO 2013154325A1 KR 2013002954 W KR2013002954 W KR 2013002954W WO 2013154325 A1 WO2013154325 A1 WO 2013154325A1
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compound
organic electroluminescent
substituted
unsubstituted
group
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PCT/KR2013/002954
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Doo-Hyeon Moon
Nam-Kyun Kim
Jong-seok KU
Seok-Keun Yoon
Young-Jun Cho
Hyuck-Joo Kwon
Kyung-Joo Lee
Bong-Ok Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to CN201380019376.0A priority Critical patent/CN104245690A/en
Publication of WO2013154325A1 publication Critical patent/WO2013154325A1/en

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Definitions

  • the present invention relates to novel organic electroluminescent compounds and organic electroluminescent device containing the same. Specifically, the present invention relates to novel organic electroluminescent compounds showing high luminous efficiency as a red-emitting material and organic electroluminescent device containing the same.
  • An electroluminescent (EL) device is a self-light-emitting device.
  • a charge is applied between an anode and a cathode, a hole and an electron are injected from the anode and the cathode, respectively.
  • the hole and the electron are reunited to form an exciton in a light-emitting layer.
  • the EL device emits light corresponding to the wavelength of the energy gap that occurred from the transition of the exciton to a ground state.
  • the light emission is categorized as fluorescence which is the use of an exciton in a singlet state; and phosphorescence which is the use of an exciton in a triplet state.
  • fluorescence which is the use of an exciton in a singlet state
  • phosphorescence which is the use of an exciton in a triplet state.
  • quantum mechanics phosphorescent light emitting materials enhance luminous efficiency by about four (4) times compared to fluorescent light emitting materials.
  • a luminescent dye (dopant) can be used in combination with a host material as a light emitting material to improve color purity, luminous efficiency, and stability.
  • host materials greatly influence the efficiency and the performance of the EL device when using a host material/dopant system as a light emitting material, their selection is important.
  • conventional phosphorescent materials such as 4,4-N,N-dicarbazolebiphenyl (CBP) provides a current efficiency higher than fluorescent materials, the driving voltage is high. Thus, there are less advantages in terms of power efficiency. Further, the luminous efficiency and operating lifespan of the device still need improvement.
  • WO 2011/132683 and WO 2011/132684 disclose biscarbazole derivatives having electron and hole transporting capability, the use of the compounds as phosphorescent host materials and EL devices comprising the compounds.
  • the compounds of the publications are not satisfactory in power efficiency and luminous efficiency.
  • the present invention is accomplished to fulfill the above needs in the field.
  • the objective of the present invention is to provide an organic electroluminescent compound having high luminous efficiency and power efficiency; and an organic electroluminescent device comprising the organic electroluminescent compound.
  • X 1 and X 2 each independently represent CR 0 or N, where at least one of the X 1 and X 2 is N;
  • R 0 represents a hydrogen, a substituted or unsubstituted (C 1 -C 30 )alkyl group, a substituted or unsubstituted (C 6 -C 30 )aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group;
  • Ar 1 and Ar 2 each independently represent a hydrogen, a substituted or unsubstituted (C 6 -C 30 )aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group;
  • one of the two substituents marked with * has the following formula II and the other one is a hydrogen, a substituted or unsubstituted (C 6 -C 30 )aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group;
  • L 1 , L 2 and L 3 each independently represent a single bond or a substituted or unsubstituted (C 6 -C 30 )arylene;
  • A, B, C and D each independently represent a substituted or unsubstituted (C 6 -C 30 ) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the A and D rings can form a fused ring with an adjacent substituent(s);
  • E is a compound represented by formula III below;
  • F and G each independently represent a substituted or unsubstituted (C 6 -C 30 ) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the F and G rings can form a fused ring with an adjacent substituent(s);
  • q is an integer of 0 or 1.
  • X and Y each independently represent NR 1 , CR 2 R 3 , O or S;
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen, a substituted or unsubstituted (C 1 -C 30 )alkyl group, a substituted or unsubstituted (C 6 -C 30 )aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group;
  • n, o, p, r and s each independently represent an integer of 0 or 1, where n+o+p is an integer of 1 or more;
  • the organic electroluminescent compounds according to the present invention can provide high luminous efficiency and power efficiency. Therefore, it is possible to manufacture an organic electroluminescent device with high current efficiency and low power consumption by using the compounds of the present invention.
  • the present invention relates to an organic electroluminescent compound represented by formula I above, an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the material.
  • (C 1 -C 30 )alkyl is meant to be a linear or branched alkyl having having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • (C 2 -C 30 ) alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C 2 -C 30 )alkynyl is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C 1 -C 30 )alkoxy is a linear or branched alkoxy having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, etc.
  • (C 3 -C 30 )cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 10, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (C 6 -C 30 )aryl(ene) is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 18, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, fluoranthenyl, etc.
  • (C 6 -C 30 ) aromatic ring is a monocyclic or fused ring having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 18, and includes benzene, naphthalene, anthracene, pyrene, chrysene, acenaphtylene, etc.
  • “5- to 60-membered heteroaromatic ring” is a monocyclic or fused ring having at least one, preferably 1 to 4 heteroatoms, and 5 to 60, preferably 5 to 30 ring backbone atoms, and includes pyrazole, imidazole, pyrazine, pyrimidine, indazole, pyrimidine, purine, phthalazine, naphtylidine, quinoxaline, quinazoline, cinnoline, pteridine, perimidine, phenanthroline, pyrroloimidazole, pyrrolotriazole, pyrazoloimidazole, pyrazolotriazole, pyrazolopyrimidine, pyrazolotriazine, imidazoimidazole, imidazopyridine, imidazopyrazine, triazolopyridine, benzoimidazole, naphtoimidazole, benzoxazole, naphtoxazole, benzothi
  • halogen includes F, Cl, Br and I.
  • the (C 1 -C 30 )alkyl, (C 6 -C 30 )aryl, 5- to 60-membered heteroaryl, (C 6 -C 30 ) aromatic ring, 5- to 60-membered heteroaromatic ring each independently can be substituted with at least one substituents selected from the group consisting of a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C 1 -C 30 )alkyl group; a halo(C 1 -C 30 )alkyl group; a (C 2 -C 30 )alkenyl group; a (C 2 -C 30 )alkynyl group; a (C 1 -C 30 )alkoxy group; a (C 1 -C 30 )alkylthio group; a (C 3 -C 30 )cycloalkyl group; a (C 3 -C 30 )cycloalkeny
  • an organic electroluminescent compound represented by any one of the following formulae 1 to 4:
  • X 1 and X 2 each independently represent CR 0 or N, where at least one of the X 1 and X 2 is N;
  • Ar 1 , Ar 2 and Ar 3 each independently represent a hydrogen, a substituted or unsubstituted (C 6 -C 30 )aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group; preferably each independently represent a hydrogen, a substituted or unsubstituted (C 6 -C 18 )aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; more preferably each independently represent a hydrogen, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, bezothiopheno[2,3-c]pyridinyl or benzofuro[2,3-c]pyridinyl;
  • L 1 , L 2 and L 3 each independently represent a single bond or a substituted or unsubstituted (C 6 -C 30 )arylene; preferably each independently represent a single bond or a substituted or unsubstituted (C 6 -C 18 )arylene; more preferably each independently represent a single bond or phenylene;
  • A, B, C and D each independently represent a substituted or unsubstituted (C 6 -C 30 ) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the A and D rings can form a fused ring with an adjacent substituent(s); preferably each independently represent a substituted or unsubstituted (C 6 -C 18 ) aromatic ring or a substituted or unsubstituted 5- to 30-membered heteroaromatic ring; more preferably each independently represent benzene, naphthalene, dibenzofuran, dibenzothiophen or 9,9-dimethylfluorene ;
  • E is a compound represented by formula 5 below;
  • F and G each independently represent a substituted or unsubstituted (C 6 -C 30 ) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the F and G rings can form a fused ring with an adjacent substituent(s);
  • q is an integer of 0 or 1.
  • X 3 , X and Y each independently represent NR 1 , CR 2 R 3 , O or S;
  • R 0 , R 1 , R 2 and R 3 each independently represent a hydrogen, a substituted or unsubstituted (C 1 -C 30 )alkyl group, a substituted or unsubstituted (C 6 -C 30 )aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group; and
  • n, o and p each independently represent an integer of 0 or 1, where n+o+p is an integer of 1 or more;
  • the organic electroluminescent compounds represented by formula 1 include the compounds represented by formulae 6 to 20, but are not limited thereto:
  • Ar 1 , Ar 2 , L 1 , L 2 , X and Y are as defined in Formula 1;
  • R 5 to R 7 each independently represent a hydrogen, a substituted or unsubstituted (C 6 -C 30 )aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group.
  • the organic electroluminescent compounds represented by formula 2 include the compounds represented by formulae 21 to 24, but are not limited thereto:
  • Ar 1 , Ar 2 , L 1 , X and Y are as defined in Formula 2;
  • R 5 and R 6 each independently represent a hydrogen, a substituted or unsubstituted (C 6 -C 30 )aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group.
  • the organic electroluminescent compounds represented by formula 3 include the compounds represented by formulae 25 to 27, but are not limited thereto:
  • Ar 1 , Ar 2 , R 1 , L 3 , X and Y are as defined in Formula 3.
  • the organic electroluminescent compounds represented by formula 4 include the compounds represented by formulae 28 to 31, but are not limited thereto:
  • Ar 1 , Ar 2 , X 3 and Y are as defined in Formula 4.
  • the representative organic electroluminescent compounds of the present invention include the following compounds, but are not limited thereto:
  • organic electroluminescent compounds of the present invention can be prepared by a synthetic method known to a person skilled in the art such as a Suzuki reaction.
  • an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the material.
  • the material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
  • the organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between the first and second electrodes.
  • the organic layer may comprise at least one organic electroluminescent compound of formula I according to the present invention.
  • the organic layer comprises a light-emitting layer, and at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
  • Transparent and conductive materials such as Indium-Tin oxide (ITO), Tin oxide (SnO 2 ), Zinc oxide (ZnO), etc.
  • ITO Indium-Tin oxide
  • Tin oxide Tin oxide
  • ZnO Zinc oxide
  • the organic electroluminescent compound according to the present invention can be included in the organic layer, preferably in the light-emitting layer.
  • the compound can be included as a host material.
  • the light-emitting layer further comprises at least one dopant. If necessary, a compound other than the organic electroluminescent compound according to the present invention may be included in the light-emitting layer.
  • the dopants applied to the organic electroluminescent device of the present invention are not specifically limited, but are preferably one or more phosphorescent dopants.
  • the phosphorescent dopant materials may be compounds of copper (Cu), lutenium (Lu), Rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), etc., preferably may be complex compounds of copper (Cu), osmium (Os), iridium (Ir), and platinum (Pt), more preferably complex compounds of iridium (Ir) and platinum (Pt), and even more preferably ortho metallated iridium complex compounds.
  • the dopant materials include the following:
  • the organic electroluminescent device of the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound, besides the organic electroluminescent compound according to the present invention; and may further include a yellow or orange light-emitting layer, if necessary.
  • a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
  • a surface layer may be preferably placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
  • a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • Such a surface layer provides operation stability for the organic electroluminescent device.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • the present invention further provides the material for the organic electroluminescent device.
  • the material comprises a first host material and a second host material; and the first host material may comprise the organic electroluminescent compounds of the present invention.
  • the first host material and the second host material may be in the range of 1:99 to 99:1 in a weight ratio.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, flow coating methods can be used.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • An OLED device was produced using the organic electroluminescent compound according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 1 ,N 1’ -([1,1’-biphenyl]-4,4’-diyl)bis(N 1 -(naphthalene-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • compound 42 according to the present invention was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-7 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and deposited in a doping amount of 4 wt% of the dopant, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[ d ]imidazole was introduced into one cell and lithium quinolate (Liq) was introduced into another cell.
  • Liq lithium quinolate
  • the two materials were evaporated at the same rate and were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr prior to use.
  • the produced OLED device showed a red emission having a luminance of 1335 cd/m 2 and a current density of 7.7 mA/cm 2 .
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound 95 as a host, and compound D-7 as a dopant.
  • the produced OLED device showed a red emission having a luminance of 1554 cd/m 2 and a current density of 8.6 mA/cm 2 .
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound 96 as a host, and compound D-11 as a dopant.
  • the produced OLED device showed a red emission having a luminance of 1290 cd/m 2 and a current density of 15.0 mA/cm 2 .
  • Comparative Example 1 Production of an OLED device using conventional
  • An OLED device was produced in the same manner as in Device Example 1, except for depositing the light emitting layer having a thickness of 30 nm on the hole transport layer using 4,4'-N,N'-dicarbazole-biphenyl as a host, and compound D-11 as a dopant; and depositing aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate to form a hole blocking layer having a thickness of 10 nm on the light emitting layer.
  • the produced OLED device showed a red emission having a luminance of 1000 cd/m 2 and a current density of 20.0 mA/cm 2 .
  • the organic electroluminescent compounds of the present invention have superior luminous efficiency as a red-emitting material over conventional host compounds.
  • the excellent luminous efficiency and improved power efficiency of an organic electroluminescent device can be achieved without a hole blocking layer when the organic electroluminescent compound is used as a host material.

Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound shows high luminous efficiency as a red-emitting material compared to conventional compounds. Further, the excellent luminous efficiency and improved power efficiency of an organic electroluminescent device can be achieved without a hole blocking layer when the organic electroluminescent compound is used as a host material.

Description

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE CONTAINING THE SAME
The present invention relates to novel organic electroluminescent compounds and organic electroluminescent device containing the same. Specifically, the present invention relates to novel organic electroluminescent compounds showing high luminous efficiency as a red-emitting material and organic electroluminescent device containing the same.
An electroluminescent (EL) device is a self-light-emitting device. When a charge is applied between an anode and a cathode, a hole and an electron are injected from the anode and the cathode, respectively. The hole and the electron are reunited to form an exciton in a light-emitting layer. The EL device emits light corresponding to the wavelength of the energy gap that occurred from the transition of the exciton to a ground state.
The light emission is categorized as fluorescence which is the use of an exciton in a singlet state; and phosphorescence which is the use of an exciton in a triplet state. In view of quantum mechanics, phosphorescent light emitting materials enhance luminous efficiency by about four (4) times compared to fluorescent light emitting materials.
Meanwhile, in the EL device, a luminescent dye (dopant) can be used in combination with a host material as a light emitting material to improve color purity, luminous efficiency, and stability.
Since, host materials greatly influence the efficiency and the performance of the EL device when using a host material/dopant system as a light emitting material, their selection is important. Though the conventional phosphorescent materials such as 4,4-N,N-dicarbazolebiphenyl (CBP) provides a current efficiency higher than fluorescent materials, the driving voltage is high. Thus, there are less advantages in terms of power efficiency. Further, the luminous efficiency and operating lifespan of the device still need improvement.
WO 2011/132683 and WO 2011/132684 disclose biscarbazole derivatives having electron and hole transporting capability, the use of the compounds as phosphorescent host materials and EL devices comprising the compounds. However, the compounds of the publications are not satisfactory in power efficiency and luminous efficiency.
The present invention is accomplished to fulfill the above needs in the field. The objective of the present invention is to provide an organic electroluminescent compound having high luminous efficiency and power efficiency; and an organic electroluminescent device comprising the organic electroluminescent compound.
After committed study to achieve the above object, the present inventors found that the efficiency of red-emitting was improved when the specific position (marked with *) of the following formula I is substituted with a specific substituent where aromatic ring(s) or heteroaromatic ring(s) are linked via single bond(s), or single bond(s) and at least one atom selected from the group consisting of N, S, O, and C:
[Formula I]
Figure PCTKR2013002954-appb-I000001
wherein
X1 and X2 each independently represent CR0 or N, where at least one of the X1 and X2 is N;
R0 represents a hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group;
Ar1 and Ar2 each independently represent a hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group;
one of the two substituents marked with * has the following formula II and the other one is a hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group;
[Formula II]
Figure PCTKR2013002954-appb-I000002
wherein
L1, L2 and L3 each independently represent a single bond or a substituted or unsubstituted (C6-C30)arylene;
A, B, C and D each independently represent a substituted or unsubstituted (C6-C30) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the A and D rings can form a fused ring with an adjacent substituent(s);
E is a compound represented by formula III below;
[Formula III]
Figure PCTKR2013002954-appb-I000003
wherein
F and G each independently represent a substituted or unsubstituted (C6-C30) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the F and G rings can form a fused ring with an adjacent substituent(s);
Z is a single bond; and
q is an integer of 0 or 1.
X and Y each independently represent NR1, CR2R3, O or S;
X3 represents NR1, CR2R3, O or S in the case where r=0 and represents N or CR4 in the case where r=1;
R1, R2, R3 and R4 each independently represent a hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group;
m, n, o, p, r and s each independently represent an integer of 0 or 1, where n+o+p is an integer of 1 or more;
with the proviso that the following compounds are excluded from the compounds represented by the formula I.
Figure PCTKR2013002954-appb-I000004
The organic electroluminescent compounds according to the present invention can provide high luminous efficiency and power efficiency. Therefore, it is possible to manufacture an organic electroluminescent device with high current efficiency and low power consumption by using the compounds of the present invention.
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The present invention relates to an organic electroluminescent compound represented by formula I above, an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the material.
Herein, “(C1-C30)alkyl” is meant to be a linear or branched alkyl having having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
Herein, “(C2-C30) alkenyl” is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
Herein, “(C2-C30)alkynyl” is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
Herein, “(C1-C30)alkoxy” is a linear or branched alkoxy having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, etc.
Herein, “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 10, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
Herein, “3- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatoms selected from the group consisting of B, N, O, S, P(=O), Si and P, preferably O, S and N, and 3 to 7 ring backbone atoms, and includes tetrahydrofurane, pyrrolidine, thiolan, tetrahydropyran, etc.
Herein, “(C6-C30)aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 18, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, fluoranthenyl, etc.
“5- to 60-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, P(=O), Si and P, and 5 to 60, preferably 5 to 30 ring backbone atoms; may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, bezothiopheno[2,3-c]pyridinyl, benzofuro[2,3-c]pyridinyl, etc.
Herein, “(C6-C30) aromatic ring” is a monocyclic or fused ring having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 18, and includes benzene, naphthalene, anthracene, pyrene, chrysene, acenaphtylene, etc. “5- to 60-membered heteroaromatic ring” is a monocyclic or fused ring having at least one, preferably 1 to 4 heteroatoms, and 5 to 60, preferably 5 to 30 ring backbone atoms, and includes pyrazole, imidazole, pyrazine, pyrimidine, indazole, pyrimidine, purine, phthalazine, naphtylidine, quinoxaline, quinazoline, cinnoline, pteridine, perimidine, phenanthroline, pyrroloimidazole, pyrrolotriazole, pyrazoloimidazole, pyrazolotriazole, pyrazolopyrimidine, pyrazolotriazine, imidazoimidazole, imidazopyridine, imidazopyrazine, triazolopyridine, benzoimidazole, naphtoimidazole, benzoxazole, naphtoxazole, benzothiazole, naphtothiazole, benzotriazole, tetrazaindene, triazine, carbazole, etc.
Herein, “halogen” includes F, Cl, Br and I.
The (C1-C30)alkyl, (C6-C30)aryl, 5- to 60-membered heteroaryl, (C6-C30) aromatic ring, 5- to 60-membered heteroaromatic ring each independently can be substituted with at least one substituents selected from the group consisting of a halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; a (C1-C30)alkyl group; a halo(C1-C30)alkyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a (C1-C30)alkoxy group; a (C1-C30)alkylthio group; a (C3-C30)cycloalkyl group; a (C3-C30)cycloalkenyl group; a 3- to 7- membered heterocycloalkyl group; a (C6-C30)aryl group unsubstituted or substituted with a 5- to 60- membered heteroaryl group; a (C6-C30)aryloxy group; a (C6-C30)arylthio group; a 5- to 60- membered heteroaryl group unsubstituted or substituted with a (C6-C30)aryl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyl di(C6-C30)arylsilyl group; an amino group; a mono- or di- (C1-C30)alkylamino group; a mono- or di- (C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a (C1-C30)alkylcarbonyl group; a (C1-C30)alkoxycarbonyl group; a (C6-C30)arylcarbonyl group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; and a (C1-C30)alkyl(C6-C30)aryl group, preferably can be substituted with at least one substituents selected from the group consisting of a halogen; a hydroxyl group; a (C1-C30)alkyl group; a (C1-C30)alkoxy group; a halo(C1-C30)alkyl group; a (C6-C30)aryl group; a 5- to 60- membered heteroaryl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyl di(C6-C30)arylsilyl group; an amino group; a mono- or di- (C1-C30)alkylamino group; a mono- or di- (C6-C30)arylamino group; and a (C1-C30)alkyl(C6-C30)arylamino group.
In one embodiment of the present invention provides an organic electroluminescent compound represented by any one of the following formulae 1 to 4:
[Formula 1]
Figure PCTKR2013002954-appb-I000005
[Formula 2]
Figure PCTKR2013002954-appb-I000006
[Formula 3]
Figure PCTKR2013002954-appb-I000007
[Formula 4]
Figure PCTKR2013002954-appb-I000008
wherein
X1 and X2 each independently represent CR0 or N, where at least one of the X1 and X2 is N;
Ar1, Ar2 and Ar3 each independently represent a hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group; preferably each independently represent a hydrogen, a substituted or unsubstituted (C6-C18)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; more preferably each independently represent a hydrogen, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, bezothiopheno[2,3-c]pyridinyl or benzofuro[2,3-c]pyridinyl;
L1, L2 and L3 each independently represent a single bond or a substituted or unsubstituted (C6-C30)arylene; preferably each independently represent a single bond or a substituted or unsubstituted (C6-C18)arylene; more preferably each independently represent a single bond or phenylene;
A, B, C and D each independently represent a substituted or unsubstituted (C6-C30) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the A and D rings can form a fused ring with an adjacent substituent(s); preferably each independently represent a substituted or unsubstituted (C6-C18) aromatic ring or a substituted or unsubstituted 5- to 30-membered heteroaromatic ring; more preferably each independently represent benzene, naphthalene, dibenzofuran, dibenzothiophen or 9,9-dimethylfluorene ;
E is a compound represented by formula 5 below;
[Formula 5]
Figure PCTKR2013002954-appb-I000009
wherein
F and G each independently represent a substituted or unsubstituted (C6-C30) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the F and G rings can form a fused ring with an adjacent substituent(s);
Z is a single bond; and
q is an integer of 0 or 1.
X3, X and Y each independently represent NR1, CR2R3, O or S;
R0, R1, R2 and R3 each independently represent a hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group; and
m, n, o and p each independently represent an integer of 0 or 1, where n+o+p is an integer of 1 or more;
with the proviso that the following compounds are excluded from the compounds represented by any one of formulae 1 to 4.
Figure PCTKR2013002954-appb-I000010
The organic electroluminescent compounds represented by any one of formulae 1 to 4 include a compound wherein m=1, n=1, o=0, p=0 and L2 is a single bond; a compound wherein m=0, n=1, o=1 and p=0; a compound wherein m=0, n=1, o=0 and p=1; a compound wherein m=0, n=0, o=0 and p=1; a compound wherein m=1, n=1, o=0, p=1 and L2 is a single bond, etc.
The organic electroluminescent compounds represented by formula 1 include the compounds represented by formulae 6 to 20, but are not limited thereto:
Figure PCTKR2013002954-appb-I000011
Figure PCTKR2013002954-appb-I000012
Figure PCTKR2013002954-appb-I000013
Figure PCTKR2013002954-appb-I000014
Figure PCTKR2013002954-appb-I000015
wherein,
Ar1, Ar2, L1, L2, X and Y are as defined in Formula 1;
R5 to R7 each independently represent a hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group.
The organic electroluminescent compounds represented by formula 2 include the compounds represented by formulae 21 to 24, but are not limited thereto:
Figure PCTKR2013002954-appb-I000016
Figure PCTKR2013002954-appb-I000017
wherein,
Ar1, Ar2, L1, X and Y are as defined in Formula 2;
R5 and R6 each independently represent a hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group.
The organic electroluminescent compounds represented by formula 3 include the compounds represented by formulae 25 to 27, but are not limited thereto:
Figure PCTKR2013002954-appb-I000018
wherein,
Ar1, Ar2, R1, L3, X and Y are as defined in Formula 3.
The organic electroluminescent compounds represented by formula 4 include the compounds represented by formulae 28 to 31, but are not limited thereto:
Figure PCTKR2013002954-appb-I000019
Figure PCTKR2013002954-appb-I000020
wherein,
Ar1, Ar2, X3 and Y are as defined in Formula 4.
The representative organic electroluminescent compounds of the present invention include the following compounds, but are not limited thereto:
Figure PCTKR2013002954-appb-I000021
Figure PCTKR2013002954-appb-I000022
Figure PCTKR2013002954-appb-I000023
Figure PCTKR2013002954-appb-I000024
Figure PCTKR2013002954-appb-I000025
Figure PCTKR2013002954-appb-I000026
Figure PCTKR2013002954-appb-I000027
Figure PCTKR2013002954-appb-I000028
Figure PCTKR2013002954-appb-I000029
Figure PCTKR2013002954-appb-I000030
Figure PCTKR2013002954-appb-I000031
Figure PCTKR2013002954-appb-I000032
Figure PCTKR2013002954-appb-I000033
Figure PCTKR2013002954-appb-I000034
Figure PCTKR2013002954-appb-I000035
Figure PCTKR2013002954-appb-I000036
Figure PCTKR2013002954-appb-I000037
Figure PCTKR2013002954-appb-I000038
Figure PCTKR2013002954-appb-I000039
Figure PCTKR2013002954-appb-I000040
Figure PCTKR2013002954-appb-I000041
Figure PCTKR2013002954-appb-I000042
Figure PCTKR2013002954-appb-I000043
The organic electroluminescent compounds of the present invention can be prepared by a synthetic method known to a person skilled in the art such as a Suzuki reaction.
In another embodiment of the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the material. The material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used in organic electroluminescent materials.
The organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between the first and second electrodes. The organic layer may comprise at least one organic electroluminescent compound of formula I according to the present invention.
One of the first and second electrodes is an anode, and the other is a cathode. The organic layer comprises a light-emitting layer, and at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, and a hole blocking layer.
Transparent and conductive materials, such as Indium-Tin oxide (ITO), Tin oxide (SnO2), Zinc oxide (ZnO), etc., can be used as the material for anode. Lithium, magnesium, calcium, aluminum, Al:Li, Ba:Li, Ca:Li, etc., which have small work function, can be used as the material for cathode.
The organic electroluminescent compound according to the present invention can be included in the organic layer, preferably in the light-emitting layer. When used in the light-emitting layer, the compound can be included as a host material. Preferably, the light-emitting layer further comprises at least one dopant. If necessary, a compound other than the organic electroluminescent compound according to the present invention may be included in the light-emitting layer.
The dopants applied to the organic electroluminescent device of the present invention are not specifically limited, but are preferably one or more phosphorescent dopants. The phosphorescent dopant materials may be compounds of copper (Cu), lutenium (Lu), Rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), etc., preferably may be complex compounds of copper (Cu), osmium (Os), iridium (Ir), and platinum (Pt), more preferably complex compounds of iridium (Ir) and platinum (Pt), and even more preferably ortho metallated iridium complex compounds.
The dopant materials include the following:
Figure PCTKR2013002954-appb-I000044
Figure PCTKR2013002954-appb-I000045
Figure PCTKR2013002954-appb-I000046
Figure PCTKR2013002954-appb-I000047
Figure PCTKR2013002954-appb-I000048
Figure PCTKR2013002954-appb-I000049
The organic electroluminescent device of the present invention may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound, besides the organic electroluminescent compound according to the present invention; and may further include a yellow or orange light-emitting layer, if necessary.
In the organic electroluminescent device according to the present invention, a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
According to the present invention, at least one layer (hereinafter, "a surface layer”) may be preferably placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer and a metal oxide layer. Specifically, a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
The present invention further provides the material for the organic electroluminescent device. The material comprises a first host material and a second host material; and the first host material may comprise the organic electroluminescent compounds of the present invention. The first host material and the second host material may be in the range of 1:99 to 99:1 in a weight ratio.
In order to form each layer of the organic electroluminescent device according to the present invention, dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, flow coating methods can be used.
When using a wet film-forming method, a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
Hereinafter, the organic electroluminescent compound, the preparation method of the compound, and the luminescent properties of the device comprising the compound of the present invention will be explained in detail with reference to the following examples.
Hereinafter, the acronyms used in the examples are as follows:
EtOH: ethanol, DMF: dimethylformamide, EDA:ethylenediamine
EA: ethylacetate, MC: methylene chloride, THF: tetrahydrofuran
Tol:toluene, rt: room temperature
Example 1: Preparation of compound 42
Figure PCTKR2013002954-appb-I000050
Preparation of compound 42-3
After dissolving compound 42-1 (14 g, 48.76 mmol), compound 42-2 (10 g, 40.63 mmol), K2CO3 (13.5 g, 97.52 mmol), and tetrakis(triphenylphosphine)palladium(O) [Pd(PPh3)4] (2.35 g, 2.03 mmol) in a mixture solvent of toluene (200 mL), EtOH (50 mL), and purified water (50 mL), the mixture was stirred for 3 hours at 90-100°C. Then, the mixture was cooled to room temperature and two phase mixture of organic layer/aqueous layer was obtained. The aqueous layer was removed, and the organic layer was concentrated and then separated with a column to obtain compound 42-3 (12 g, 72 %).
Figure PCTKR2013002954-appb-I000051
Preparation of compound 42-5
After dissolving compound 42-3 (20 g, 49 mmol) and compound 42-4 (15.6 g, 73.6 mmol) in a DMF (500 mL), NaH (60 %, 2.4 g, 58.8 mmol) was added to the mixture in room temperature. The mixture was stirred for 12 hours, and then the organic layer was extracted with EA. The obtained product was concentrated by reducing pressure. The concentrated solution was separated with a column to obtain compound 42-5 (21 g, 76 %).
Figure PCTKR2013002954-appb-I000052
Preparation of compound 42
After dissolving compound 42-5 (20 g, 35 mmol), compound 42-6 (8.3 g, 42 mmol), K2CO3 (14.5 g, 105 mmol), and Pd(PPh3)4 (2.02 g, 1.75 mmol) in a mixture solvent of toluene (200 mL), EtOH (40 mL), and purified water (40 mL), the mixture was stirred for 3 hours at 90-100°C. Then, the mixture was cooled to room temperature and two phase mixture of organic layer/aqueous layer was obtained. The aqueous layer was removed, and the organic layer was concentrated and then separated with a column to obtain compound 42 (16.4 g, 68 %).
Example 2: Preparation of compound 43
Figure PCTKR2013002954-appb-I000053
Preparation of compound 43-4
After dissolving compound 43-3 (14 g, 34.3 mmol), 1-bromo-4-iodobenzene (48.5 g, 171.4 mmol), CuI (3.3 g, 17.1 mmol), K3PO4 (21.8 g, 102.9 mmol) and EDA (2.3 mL, 34.3 mmol) in a toluene (500 mL), the mixture was stirred for 1 day under reflux. The organic layer was extracted with EA and distilled under reduced pressure. The obtained product was separated with MC/hexane in a column to obtain compound 43-4 (15.5 g, 80.1 %).
Figure PCTKR2013002954-appb-I000054
Preparation of compound 43-5
After dissolving compound 43-4 (15.5 g, 27.5 mmol) in THF (250 mL), n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) was added to the mixture at -78°C and the mixture was stirred for 1 hour. Then, B(OMe)3 (12.6 mL, 55 mmol) was added slowly to the mixture, and the mixture was stirred for 2 hours. The mixture was quenched by adding 2 M HCl, and the organic layer was extracted with distilled water and EA. The obtained product was recrystallized with MC and hexane to obtain compound 43-5 (8.7 g, 60 %).
Figure PCTKR2013002954-appb-I000055
Preparation of compound 43-7
After dissolving compound 43-5 (9.5 g, 18 mmol), compound 43-6 (7.6 g, 36 mmol), Pd(PPh3)4 (994 mg, 0.86 mmol), and Na2CO3 (4.8 g, 45.3 mmol) in a mixture solvent of toluene (100 mL), EtOH (20 mL), and distilled water (20 mL), the mixture was stirred for 2 hours at 90°C. The organic layer was extracted with distilled water and EA, and separated with MC and hexane in a column to obtain compound 43-7 (10 g, 85 %).
Figure PCTKR2013002954-appb-I000056
Preparation of compound 43
After dissolving compound 43-7 (10 g, 15.45 mmol), compound 43-8 (4.5 g, 21.2 mmol), Pd(PPh3)4 (890 mg, 0.77 mmol), and K2CO3 (6.4 g, 46.35 mmol), in a mixture solvent of toluene (80 mL), EtOH (10 mL), and distilled water (10 mL), the mixture was stirred for 2 hours at 90°C. The organic layer was extracted with distilled water and EA, and separated with MC and hexane in a column to obtain compound 43 (7.45 g, 62 %).
Example 3: Preparation of compound 40
Figure PCTKR2013002954-appb-I000057
Preparation of compound 40
After dissolving compound 40-5 (20 g, 35 mmol), compound 40-6 (9.6 g, 42 mmol), K2CO3 (14.5 g, 105 mmol), and Pd(PPh3)4 (2.02 g, 1.75 mmol) in a mixture solvent of toluene (200 mL), EtOH (40 mL), and purified water (40 mL), the mixture was stirred for 3 hours at 90-100°C. Then, the mixture was cooled to room temperature and two phase mixture of organic layer/aqueous layer was obtained. The aqueous layer was removed, and the organic layer was concentrated and then separated with a column to obtain compound 40 (16.8 g, 67 %).
Example 4: Preparation of compound 95
Figure PCTKR2013002954-appb-I000058
Preparation of compound 95-3
After dissolving compound 95-1 (127 g, 0.60 mmol), compound 95-2 (100 g, 0.50 mmol), K2CO3 (159 g, 1.50 mmol), and Pd(PPh3)4 (29 g, 0.03 mmol) in a mixture solvent of toluene (3 L), EtOH (750 mL), and purified water (750 mL), the mixture was stirred for 1 day under reflux. The obtained organic layer was extracted with ethylacetate (2 L) and washed with distilled water (500 mL). The obtained organic layer was dried with anhydrous MgSO4 and the organic solvent was removed under the reduced pressure. The crude product was purified through silica gel column chromatography and recrystallization to obtain compound 95-3 (126 g, 87 %).
Figure PCTKR2013002954-appb-I000059
Preparation of compound 95-4
After dissolving compound 95-3 (126 g, 0.44 mmol) in triethylphosphite (1.1 L), the mixture was stirred for 5 hours at 150°C under reflux. The mixture was cooled to room temperature and distilled under reduced pressure. The crude product was purified through silica gel column chromatography and recrystallization to obtain compound 95-4 (80 g, 71 %).
Figure PCTKR2013002954-appb-I000060
Preparation of compound 95-6
After dissolving compound 95-4 (10 g, 38.87 mmol) in DMF (200 mL), NaH (2.3 g, 58.30 mmol) was slowly added to the mixture. The mixture was stirred for 30 minutes, and then compound 95-5 (7.7 g, 46.64 mmol) was added to the mixture. The obtained mixture was stirred for 4 hours. The obtained mixture was slowly added to distilled water (800 mL) and stirred for 30 minutes. The obtained solid was purified through silica gel column chromatography and recrystallization to obtain compound 95-6 (8.7 g, 53 %).
Figure PCTKR2013002954-appb-I000061
Preparation of compound 95
After dissolving compound 95-6 (4 g, 9.53 mmol), compound 95-7 (2.2 g, 11.43 mmol), K2CO3 (4 g, 28.59 mmol), and Pd(PPh3)4 (0.6 g, 0.48 mmol) in a mixture solvent of toluene (60 mL), EtOH (15 mL), and purified water (15 mL), the mixture was stirred for 1 day under reflux. The obtained organic layer was extracted with ethylacetate (100 mL) and washed with distilled water (50 mL). The obtained organic layer was dried with anhydrous MgSO4 and the organic solvent was removed under the reduced pressure. The obtained solid was purified through silica gel column chromatography and recrystallization to obtain compound 95 (2.4 g, 47 %).
Example 5: Preparation of compound 96
Figure PCTKR2013002954-appb-I000062
Preparation of compound 96-6
After dissolving compound 95-4 (10 g, 38.87 mmol), compound 96-5 (22 g, 77.74 mmol), CuI (3.7 g, 19.44 mmol), K3PO4 (20.6 g, 97.18 mmol) and EDA (2.6 mL, 38.87 mmol) in a toluene (200 mL), the mixture was stirred for 24 hours at 100°C. The mixture was cooled to room temperature, and the organic layer was extracted with ethylacetate (200 mL) and washed with distilled water (50 mL) twice. The obtained organic layer was dried with anhydrous MgSO4 and the organic solvent was removed under the reduced pressure. The obtained solid was purified through silica gel column chromatography and recrystallization to obtain compound 96-6 (12.3 g, 77 %).
Figure PCTKR2013002954-appb-I000063
Preparation of compound 96-7
After dissolving compound 96-6 (12.3 g, 29.83 mmol) in THF (150 mL), n-BuLi (17.9 mL, 44.75 mmol, 2.5 M in hexane) was added to the mixture at -78°C and the mixture was stirred for 1 hour. Then, B(Oi-pr)3 (10.3 mL, 44.75 mmol) was added to the mixture, and the mixture was stirred for 2 hours. After finishing the reaction with NH4Cl (100 mL), the organic layer was extracted with ethylacetate (200 mL) and washed with distilled water (100 mL). The obtained organic layer was dried with MgSO4 and the organic solvent was removed under the reduced pressure. The obtained solid was recrystallized to obtain compound 96-7 (8.2 g, 73 %).
Figure PCTKR2013002954-appb-I000064
Preparation of compound 96-9
After dissolving compound 96-7 (8.2 g, 21.62 mmol), compound 96-8 (3.9 g, 19.66 mmol), Na2CO3 (5.2 g, 49.15 mmol), and Pd(PPh3)4 (1.2 g, 0.98 mmol) in a mixture solvent of toluene (100 mL), EtOH (25 mL), and purified water (25 mL), the mixture was stirred for 1 day under reflux. The organic layer was extracted with ethylacetate (100 mL) and washed with distilled water (50 mL). The obtained organic layer was dried with anhydrous MgSO4 and the organic solvent was removed under the reduced pressure. The obtained solid was purified through silica gel column chromatography and recrystallization to obtain compound 96-9 (4 g, 41 %).
Figure PCTKR2013002954-appb-I000065
Preparation of compound 96
After dissolving compound 96-9 (4 g, 8.07 mmol), compound 96-10 (1.8 g, 9.68 mmol), K2CO3 (3.4 g, 24.20 mmol), and Pd(PPh3)4 (0.5 g, 0.41 mmol) in a mixture solvent of toluene (60 mL), EtOH (15 mL), and purified water (15 mL), the mixture was stirred for 1 day under reflux. The organic layer was extracted with ethylacetate (100 mL) and washed with distilled water (50 mL). The obtained organic layer was dried with anhydrous MgSO4 and the organic solvent was removed under the reduced pressure. The obtained solid was purified through silica gel column chromatography and recrystallization to obtain compound 96 (1.2 g, 24 %).
The Physical properties of the final compounds prepared according to above examples 1 to 5 are as follow:
Figure PCTKR2013002954-appb-I000066
Device Example 1: Production of an OLED device using the organic electroluminescent compound according to the present invention
An OLED device was produced using the organic electroluminescent compound according to the present invention. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N1,N1’-([1,1’-biphenyl]-4,4’-diyl)bis(N1-(naphthalene-1-yl)-N4,N4-diphenylbenzene-1,4-diamine) was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Then, N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound 42 according to the present invention was introduced into one cell of the vacuum vapor depositing apparatus as a host, and compound D-7 was introduced into another cell as a dopant. The two materials were evaporated at different rates and deposited in a doping amount of 4 wt% of the dopant, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was introduced into one cell and lithium quinolate (Liq) was introduced into another cell. The two materials were evaporated at the same rate and were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr prior to use.
The produced OLED device showed a red emission having a luminance of 1335 cd/m2 and a current density of 7.7 mA/cm2.
Device Example 2: Production of an OLED device using the organic
electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound 95 as a host, and compound D-7 as a dopant.
The produced OLED device showed a red emission having a luminance of 1554 cd/m2 and a current density of 8.6 mA/cm2.
Device Example 3: Production of an OLED device using the organic
electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound 96 as a host, and compound D-11 as a dopant.
The produced OLED device showed a red emission having a luminance of 1290 cd/m2 and a current density of 15.0 mA/cm2.
Comparative Example 1: Production of an OLED device using conventional
electroluminescent compounds
An OLED device was produced in the same manner as in Device Example 1, except for depositing the light emitting layer having a thickness of 30 nm on the hole transport layer using 4,4'-N,N'-dicarbazole-biphenyl as a host, and compound D-11 as a dopant; and depositing aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate to form a hole blocking layer having a thickness of 10 nm on the light emitting layer.
The produced OLED device showed a red emission having a luminance of 1000 cd/m2 and a current density of 20.0 mA/cm2.
It is verified that the organic electroluminescent compounds of the present invention have superior luminous efficiency as a red-emitting material over conventional host compounds. In addition, the excellent luminous efficiency and improved power efficiency of an organic electroluminescent device can be achieved without a hole blocking layer when the organic electroluminescent compound is used as a host material.

Claims (4)

  1. An organic electroluminescent compound represented by any one of the following formulae 1 to 4:
    [Formula 1]
    Figure PCTKR2013002954-appb-I000067
    [Formula 2]
    Figure PCTKR2013002954-appb-I000068
    [Formula 3]
    Figure PCTKR2013002954-appb-I000069
    [Formula 4]
    Figure PCTKR2013002954-appb-I000070
    wherein
    X1 and X2 each independently represent CR0 or N, where at least one of the X1 and X2 is N;
    Ar1, Ar2 and Ar3 each independently represent a hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group;
    L1, L2 and L3 each independently represent a single bond or a substituted or unsubstituted (C6-C30)arylene;
    A, B, C and D each independently represent a substituted or unsubstituted (C6-C30) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the A and D rings can form a fused ring with an adjacent substituent(s);
    E is a compound represented by formula 5 below;
    [Formula 5]
    Figure PCTKR2013002954-appb-I000071
    wherein
    F and G each independently represent a substituted or unsubstituted (C6-C30) aromatic ring or a substituted or unsubstituted 5- to 60-membered heteroaromatic ring, where at least one substituents on the F and G rings can form a fused ring with an adjacent substituent(s);
    Z is a single bond; and
    q is an integer of 0 or 1.
    X3, X and Y each independently represent NR1, CR2R3, O or S;
    R0, R1, R2 and R3 each independently represent a hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 60-membered heteroaryl group; and
    m, n, o and p each independently represent an integer of 0 or 1, where n+o+p is an integer of 1 or more;
    with the proviso that the following compounds are excluded from the compounds represented by any one of formulae 1 to 4.
    Figure PCTKR2013002954-appb-I000072
  2. The organic electroluminescent compound according to claim 1, wherein the compound is selected from the group consisting of:
    a compound wherein m=1, n=1, o=0, p=0 and L2 is a single bond;
    a compound wherein m=0, n=1, o=1 and p=0;
    a compound wherein m=0, n=1, o=0 and p=1;
    a compound wherein m=0, n=0, o=0 and p=1; and
    a compound wherein m=1, n=1, o=0, p=1 and L2 is a single bond.
  3. The organic electroluminescent compound according to claim 1, characterized in that the compound is selected from the group consisting of:
    Figure PCTKR2013002954-appb-I000073
    Figure PCTKR2013002954-appb-I000074
    Figure PCTKR2013002954-appb-I000075
    Figure PCTKR2013002954-appb-I000076
    Figure PCTKR2013002954-appb-I000077
    Figure PCTKR2013002954-appb-I000078
    Figure PCTKR2013002954-appb-I000079
    Figure PCTKR2013002954-appb-I000080
    Figure PCTKR2013002954-appb-I000081
    Figure PCTKR2013002954-appb-I000082
    Figure PCTKR2013002954-appb-I000083
    Figure PCTKR2013002954-appb-I000084
    Figure PCTKR2013002954-appb-I000085
    Figure PCTKR2013002954-appb-I000086
    Figure PCTKR2013002954-appb-I000087
    Figure PCTKR2013002954-appb-I000088
    Figure PCTKR2013002954-appb-I000089
    Figure PCTKR2013002954-appb-I000090
    Figure PCTKR2013002954-appb-I000091
    Figure PCTKR2013002954-appb-I000092
    Figure PCTKR2013002954-appb-I000093
    Figure PCTKR2013002954-appb-I000094
    Figure PCTKR2013002954-appb-I000095
  4. An organic electroluminescent device comprising the compound according to claim 1.
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