KR20140006707A - New organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention provides a novel organic electroluminescent compound represented by chemical formula 1 and an organic electroluminescent device including the same. The organic electroluminescent compound is a green phosphorescent host material, can be applied to the organic electroluminescent device, and can improve the luminous efficiency of the organic electroluminescent device as well as the lifetime of the device.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same.

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly to a novel organic light emitting compound used as a phosphorescent green host material and an organic light emitting device employing the same.

The most important factor determining the luminous efficiency in an OLED is a light emitting material. Fluorescent materials are widely used as the light emitting materials to date, but the development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to 4 times. Until now, iridium (III) complexes have been widely known as phosphorescent materials. Materials such as (acac) Ir (btp) 2, Ir (ppy) 3 and Firpic are known for each RGB. In particular, many phosphorescent materials have recently been studied in Japan and Europe.

CBP is the most widely known host material for phosphorescent emitters. To date, high-efficiency OLEDs using hole blocking layers such as BCP and BAlq are known, and high-performance OLEDs using BAlq derivatives as a host are known in Pioneer, Japan. I've done it.

However, existing materials have advantages in terms of luminescent properties, but they have disadvantages such as low glass transition temperature and very poor thermal stability, which can cause material changes when subjected to a high temperature deposition process under vacuum. In the OLED, power efficiency = (π / voltage) × current efficiency, so the power efficiency is inversely proportional to the voltage. To lower the power consumption of the OLED, the power efficiency must be high. In fact, OLEDs using phosphorescent materials have a significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials.However, when a conventional material such as BAlq or CBP is used as a host of phosphorescent materials, OLEDs using fluorescent materials are used. Compared with the higher driving voltage, there is no big advantage in terms of power efficiency (lm / w). In addition, since the lifetime of the OLED device is never satisfactory, development of a more stable and more excellent host material is required.

The present invention can be applied to an organic light emitting device as a phosphorescent green host material, and when applied to an organic light emitting device can lower the driving voltage, an organic light emitting compound that can improve the luminous efficiency, brightness, thermal stability and device life It aims to provide.

Another object of the present invention is to provide an organic light emitting device using the above compound.

The present invention provides an organic electroluminescent compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

Where

R1 and R3 are each independently a simple bond,

C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole , Triazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzthiazole, carbazole, quinolinyl, isoquinolinyl, indole And an arylene having 6 to 30 carbon atoms or a hetero arylene group having 5 to 60 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of pyrenyl group;

R 2 and R 4 are each independently a deuterium atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF ₃ or Si (CH ₃ ) _3, or

Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups C6-C30 aryl group or C5-C60 heteroaryl group unsubstituted or substituted by the substituent;

R 5 and R 6 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF ₃ or Si (CH ₃ ) ₃ ,

Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups Or an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms unsubstituted or substituted with a substituent;

를 형성하거나

를 형성하며, 여기서, 상기 X는 부존재 또는 단순결합이며, R9, R10 및 R11은 각각 독립적으로 C1~C5의 알킬, 페닐 또는 나프틸기이며;R5 and R6 combine with each other

Form or

Wherein X is absent or a simple bond, and R 9, R 10 and R 11 are each independently C 1 -C 5 alkyl, phenyl or naphthyl groups;

R 7 and R 8 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF ₃ or Si (CH ₃ ) _3, or

Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups Or an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms unsubstituted or substituted with a substituent;

또는

이다.R7 and R8 combine with each other

or

to be.

Further, according to the present invention,

An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

At least one of the organic thin film layers contains the organic electroluminescent compound of the present invention singly or in combination of two or more.

The organic light emitting compound according to the present invention can be applied to an organic light emitting device as a phosphorescent green host material, when applied to the organic light emitting device lowers the driving voltage, improves luminous efficiency, brightness, thermal stability and device life.

In addition, the organic electroluminescent device manufactured using the organic electroluminescent compound of the present invention has high efficiency and long life.

The present invention relates to organic electroluminescent compounds represented by the following general formula (1)

[Chemical Formula 1]

Where

R1 and R3 are each independently a simple bond,

C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole , Triazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzthiazole, carbazole, quinolinyl, isoquinolinyl, indole And an arylene having 6 to 30 carbon atoms or a hetero arylene group having 5 to 60 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of pyrenyl group;

R 2 and R 4 are each independently a deuterium atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF ₃ or Si (CH ₃ ) _3, or

Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups C6-C30 aryl group or C5-C60 heteroaryl group unsubstituted or substituted by the substituent;

R 5 and R 6 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF ₃ or Si (CH ₃ ) ₃ ,

Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups Or an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms unsubstituted or substituted with a substituent;

를 형성하거나

를 형성하며, 여기서, 상기 X는 부존재 또는 단순결합이며, R9, R10 및 R11은 각각 독립적으로 C1~C5의 알킬, 페닐 또는 나프틸기이며;R5 and R6 combine with each other

Form or

Wherein X is absent or a simple bond, and R 9, R 10 and R 11 are each independently C 1 -C 5 alkyl, phenyl or naphthyl groups;

R 7 and R 8 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF ₃ or Si (CH ₃ ) _3, or

Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups Or an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms unsubstituted or substituted with a substituent;

또는

이다.R7 and R8 combine with each other

or

to be.

The aryl having 6 to 30 carbon atoms or the heteroaryl having 5 to 60 carbon atoms may be selected from phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, Thiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzthiazole, carbazole, quinolinyl, isoquinoli Or may be neil, indole or pyrenyl.

Here, the aryl group having 6 to 30 carbon atoms or the heteroaryl group having 5 to 60 carbon atoms is an aryl group having 6 to 30 carbon atoms, a heteroarylene group having 5 to 60 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 60 carbon atoms Means included.

Preferably in the above

R1 and R3 are each independently a simple bond or a phenylene group;

R2 and R4 are each independently phenyl, naphthyl, pyridinyl, pyrimidinyl or triazinyl unsubstituted or substituted with one or more phenyl groups;

R5 and R6 are each independently a hydrogen atom, C1 ~ C5 linear or branched alkyl, or a phenyl group,

또는

를 형성하며, 상기 X는 부존재 또는 단순결합이며, R9, R10 및 R11은 각각 독립적으로 C1~C5의 알킬기 또는 페닐기이며;R5 and R6 combine with each other

or

X is absent or a simple bond, R9, R10 and R11 are each independently a C1 to C5 alkyl group or a phenyl group;

R7 and R8 are each independently a hydrogen atom or a straight or branched chain alkyl group of C1 ~ C5,

또는

를 형성할 수 있다. R7 and R8 combine with each other

or

Can be formed.

The organic light emitting compound of the present invention can be usefully used as a phosphorescent green host material.

The organic luminescent compound of the present invention may have the chemical structure shown in the following [first group (s)].

[First group (group)]

The present invention also relates to

An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of the present invention singly or in combination of two or more thereof.

The organic light emitting compound may be included in the organic electroluminescent device as a phosphorescent green host material.

The organic electroluminescent device

An anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode stacked in this order.

Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the following examples do not limit the organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention may have a structure in which a cathode (a hole injection electrode), a hole injection layer (HIL) and / or a hole transport layer (HTL), a light emitting layer (EML) Preferably, an electron blocking layer (EBL) may be additionally provided between the anode and the light emitting layer, and an electron transport layer (ETL), an electron injection layer (EIL) or a hole blocking layer (HBL) have.

In the method of manufacturing an organic electroluminescence device according to the present invention, a cathode material is coated on the surface of a substrate by a conventional method to form a cathode. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness. As the material for the positive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity may be used.

Next, a hole injection layer (HIL) material is formed on the surface of the anode by vacuum thermal deposition or spin coating using a conventional method. Examples of such hole injection layer materials include copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4' Amino) phenoxybenzene (m-MTDAPB), starburst type amines such as 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine (TCTA), 4,4' Triphenylamine (2-TNATA) or IDE406 available from Idemitsu, for example.

A hole transport layer (HTL) material is vacuum-deposited or spin coated on the surface of the hole injection layer by a conventional method to form a hole transport layer. In this case, as the hole transport layer material, bis (N- (1-naphthyl-n-phenyl)) benzidine (α-NPD), N, N'-di (naphthalen-1-yl) -N, N'-biphenyl -Benzidine (NPB) or N, N'-biphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD).

A light emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, in the case of green light emitting material, the organic light emitting compound of the present invention may be used as a phosphorescent green host material, and in addition to tris (8-hydroxyquinolinolato) aluminum (Alq3). ) Is blue, Balq (8-hydroxyquinolineberyllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl) series, Spiro Substance, Spiro-DPVBi (Spyro-4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzooxazolyl) -phenol Lithium salts), bis (biphenylvinyl) benzene, aluminum-quinoline metal complexes, metal complexes of imidazole, thiazole and oxazole, and the like.

In the case of a dopant which can be used together with a light emitting host in the light emitting layer material, IDE102, IDE105, which is available from Idemitsu as a fluorescent dopant, and tris (2-phenylpyridine) iridium (III) (Ir (ppy) as a phosphorescent dopant. 3), iridium (III) bis [(4,6-difluorophenyl) pyridinato-N, C-2 '] picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys Lett., 2001, 79, 3082-3084], platinum (II) octaethyl porphyrin (PtOEP), TBE002 (Kobiion Co.) and the like can be used.

An electron transport layer (ETL) material is formed on the surface of the light emitting layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the electron transporting material to be used is not particularly limited, and tris (8-hydroxyquinolinolato) aluminum (Alq3) can be preferably used.

Alternatively, by further forming a hole blocking layer (HBL) between the light emitting layer and the electron transporting layer and using a phosphorescent dopant together with the light emitting layer, it is possible to prevent the phenomenon that the triplet excitons or holes are diffused into the electron transporting layer.

The hole blocking layer can be formed by vacuum thermal deposition and spin coating using a hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, there is no particular limitation, but (8-hydroxyquinolinolato Lithium biphenoxide (BAlq), bathocuproine (BCP), LiF, etc. may be used as the lithium salt (Li), bis (8-hydroxy-2-methylquinolinonato)

An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the material of the electron injection layer to be used is not particularly limited, and preferably materials such as LiF, Liq, Li2O, BaO, NaCl, and CsF can be used.

Finally, a negative electrode is formed on the surface of the electron injecting layer by vacuum thermal deposition using a conventional method.

At this time, as the negative electrode material to be used, lithium, aluminum, aluminum-lithium, calcium, magnesium, (Mg-Ag) or the like may be used. In the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode capable of transmitting light.

The organic electroluminescent device according to the present invention may be manufactured in the order as described above, that is, in the order of anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode, Electron injection layer / electron transporting layer / hole blocking layer / light emitting layer / hole transporting layer / hole injecting layer / anode.

Hereinafter, a method of synthesizing the compounds of the present invention will be described with reference to representative examples. However, the method of synthesizing the compounds of the present invention is not limited to the following exemplified methods, and the compounds of the present invention can be produced by the methods exemplified below and by methods known in the art.

Preparation of compound [1]

[Reaction Scheme 1]

Preparation of intermediate compound [1-1]

Dissolve 100 g (510.09 mmol) of 2-bromo-indole, 114.1 ml (1020.19 mmol) of iodinebenzene with 1.5 L of toluene, 1.14 g (5.10 mmol) of palladium (II) acetate in nitrogen atmosphere, 499.3 g (1532.7 mmol) of cesium carbonate ) Is added. Stir at room temperature, add 4.94 mL (10.20 mmol) of tri-t-butylphosphine dropwise, and stir at reflux while slowly raising the reaction temperature. After the reaction was completed, dilute with 2 L of ethyl acetate and extract with 1.5 L of saturated salt. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and then 94.3 g (68%) of an intermediate compound [1-1] was obtained through column chromatography.

Preparation of intermediate compound [1-2]

94 g (345.41 mmol) of the intermediate compound [1-1] are dissolved with 1 L of anhydrous tetrahydrofuran in a nitrogen atmosphere, and 151.9 ml (379.9 mmol) of normal butyllithium (2.5M) are added dropwise at -78 ° C. At the same temperature, 111.7 ml (414.4 mmol) of trimethyltin chloride was added dropwise to gradually raise the temperature to room temperature for 5 hours. Distilled water and ethyl acetate are added at room temperature, and the organic layers are collected by layer separation. The organic layer is dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to obtain 104.9 g (63%) of an intermediate compound [1-2] in a clear liquid state through column chromatography.

Preparation of Intermediate Compound [1-3]

Intermediate compound [1-2] 104 g (215.63 mmol), 2-bromo-indole 42.2 g (215.63 mmol), tetrakis (triphenylphosphine) palladium 12.45 g (10.78 mmol), 1 L of dimethylformamide Stir at reflux for 5 hours in the atmosphere. After completion of the reaction, the solid produced at room temperature was filtered under reduced pressure and recrystallized from dichloromethane and methanol to obtain 46.4 g (71%) of an intermediate compound [1-3] as an off-white solid.

Preparation of Compound [1]

10 g (32.42 mmol) of intermediate compound [1-3], 6.18 g (97.28 mmol) of copper powder, 10.4 g (38.91 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, carbonic acid 13.4 g (97.28 mmol) of calcium and 500 ml of xylene were added and stirred at 180 ° C. in a nitrogen atmosphere. After completion of the reaction, distilled water and ethyl acetate were added at room temperature, and the organic layers were collected by layer separation. The organic layer is dried over anhydrous magnesium sulfate and filtered. Recrystallization from dichloromethane and methanol gave 11.8 g (68%) of the title compound [1] as an off-white solid.

Preparation of Compound [4]

[Reaction Scheme 2]

Preparation of Intermediate Compound [4-1]

25 g (198.17 mmol) of 2,2-dimethylcyclopentane-1,3-dione and 57.3 g (396.3 mmol) of phenylhydrazine chloride were added to a small amount of acetic acid, and the mixture was refluxed under a stream of nitrogen for 10 hours under 500 mL of ethanol. After cooling to room temperature, the formed product was filtered and dried to yield 35 g (65%) of the title compound [4-1] as an off-white solid.

Preparation of Intermediate Compound [4-2]

35 g (128.51 mmol) intermediate compound [4-1], 25.8 ml (257.03 mmol) bromobenzene, 228 mg (1.28 mmol) palladium (II) acetate, 62.8 g (192.76 mmol) cesium carbonate in the same manner as in Scheme 1. 25 g (56%) of an off-white solid compound [4-2] was obtained using 1.24 mL (2.57 mmol) of tri-t-butylphosphine and toluene.

Preparation of Compound [4]

10 g (28.69 mmol) of an intermediate compound [4-2], 9.2 g (34.43 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, and 5.46 g of copper powder in the same manner as in Scheme 1. (86.07 mmol), calcium carbonate 11.8 g (86.07 mmol), and xylene were used to obtain 10.8 g (65%) of the target compound [4] as an off-white solid.

Preparation of Compound [17]

Scheme 3

Preparation of Intermediate Compound [17-1]

In the same manner as in Scheme 1, an intermediate compound in an off-white solid state using 25 g (142.71 mmol) of 1-phenylpyrrolidine-2,5-dione, 41.27 g (285.42 mmol) of phenylhydrazine chloride, acetic acid, and ethanol [17- 1] 28.8 g (63%) were obtained.

Preparation of Intermediate Compound [17-2]

28 g (87.12 mmol) of an intermediate compound [17-1], 17.5 g (174.25 mmol) of bromobenzene, 195 mg (0.87 mmol) of palladium (II) acetate, 42.5 g (130.68 mmol) of cesium carbonate, 18.6 g (54%) of an off-white solid compound [17-2] was obtained using 0.84 ml (1.74 mmol) of tri-t-butylphosphine and toluene.

Preparation of Compound [17]

9 g (22.64 mmol) of intermediate compound [17-2], 9.3 g (27.17 mmol) of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine in the same manner as in Scheme 1. 4.3 g (67.92 mmol) of copper powder, 9.3 g (67.92 mmol) of calcium carbonate and xylene were used to obtain 10.0 g (63%) of the target compound in the off-white solid state.

According to the method of Schemes 1 to 3, compounds of Compounds 1 to 42 were prepared, and the results are shown in the following [Second Table].

[Second group (group)]

Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples are intended to further illustrate the present invention, and the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

Comparative Example 1

Using a compound represented by the formula (a) as a phosphorescent green host, using a compound represented by the formula (c) as a phosphorescent green dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2- yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Thus, an organic light emitting device having the following structure was manufactured: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound a + Compound c (30 nm) / Alq ₃ (30 nm) / LiF ( 0.5 nm) / Al (60 nm).

Anode cuts Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm, ultrasonically cleaned in acetone, isopropyl alcohol and pure water for 15 minutes, and then UV for 30 minutes. Ozone cleaning was used. 2-TNATA was vacuum-deposited on the substrate to form an 80 nm thick princess deposit layer. On top of the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Chemical Formula a and a compound represented by Chemical Formula c (doping rate: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Thereafter, an Alq ₃ compound was vacuum deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device as shown in Table 3. This is referred to as Comparative Sample 1.

Comparative Example 2

Using a compound represented by the formula b as a phosphorescent green host, using a compound represented by the formula c as a phosphorescent green dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2- yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Thus, an organic light emitting device having the following structure was manufactured: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound b + Compound c (30 nm) / Alq ₃ (30 nm) / LiF ( 0.5 nm) / Al (60 nm).

Anode cuts Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm, ultrasonically cleaned in acetone, isopropyl alcohol and pure water for 15 minutes, and then UV for 30 minutes. Ozone cleaning was used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Chemical Formula a and a compound represented by Chemical Formula c (doping rate: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Thereafter, the Alq ₃ compound was vacuum-deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device as shown in the following [Table 3]. This is called comparison sample 2.

<Formula a> <Formula b>

Examples 1 to 42.

In Comparative Example 1, ITO / 2-TNATA in the same manner as in Comparative Example 1, except that the compounds represented by Chemical Formulas 1 to 42 disclosed in Synthesis Example were used as the phosphorescent green host compounds instead of the light emitting layer phosphorescent host compound a. (80 nm) / α-NPD (30 nm) / [one of phosphorescent green host compounds 1 to 42 + compound c (10%)] (30 nm) / Alq ₃ (30 nm) / LiF (0.5 nm) / Al ( An organic light emitting device having a structure of 60 nm) was prepared. These are referred to as Samples 1 to 42, respectively.

Evaluation Example 1: Evaluation of Luminescence Characteristics of Comparative Samples 1 and 2 and Samples 1 to 42

For Comparative Samples 1, 2 and Samples 1 to 42, luminescence brightness, luminescence efficiency, and luminescence peak were evaluated using Keithleysourcemeter "2400" and KONIKA MINOLTA "CS-2000", and the results were summarized as follows. Viii). The samples showed green emission peaks in the range of 511-517 nm.

[Group 3]

As confirmed from the above [Table 3], Samples 1 to 42 exhibited improved luminescence properties compared to Comparative Samples 1 and 2.

Evaluation Example 2 Evaluation of Life Characteristics of Comparative Samples 1, 2, and 1 to 42

For Comparative Samples 1 and 2 and Samples 1 to 42, the time at which the life reached 97% based on 3000 nits was measured using ENC technology's LTS-1004AC life measuring device, respectively. Table group (群)] is shown.

[Group 4]

As confirmed from the above [Table 4], Samples 1 to 42 exhibited improved life characteristics compared to Comparative Samples 1 and 2.

Claims (8)

An organic light-emitting compound represented by the following formula (1):
[Chemical Formula 1]

In this formula,
R1 and R3 are each independently a simple bond,
C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole , Triazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzthiazole, carbazole, quinolinyl, isoquinolinyl, indole And an arylene having 6 to 30 carbon atoms or a hetero arylene group having 5 to 60 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of pyrenyl group;
R 2 and R 4 are each independently a deuterium atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF ₃ or Si (CH ₃ ) _3, or
Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups C6-C30 aryl group or C5-C60 heteroaryl group unsubstituted or substituted by the substituent;
R 5 and R 6 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF ₃ or Si (CH ₃ ) ₃ ,
Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups Or an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms unsubstituted or substituted with a substituent;
R5 and R6 combine with each other

Form or

Wherein X is absent or a simple bond, and R 9, R 10 and R 11 are each independently C 1 -C 5 alkyl, phenyl or naphthyl groups;
R 7 and R 8 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 alkoxy, halogen, nitrile, CF ₃ or Si (CH ₃ ) _3, or
Deuterium atom, C1-C10 straight or branched chain alkyl, C1-C10 alkoxy, halogen, nitrile, CF ₃ , Si (CH ₃ ) ₃ , phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole At least one selected from the group consisting of pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyrazinyl, pyridazinyl pyridinyl, pyrimidinyl and triazinyl groups Or an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms unsubstituted or substituted with a substituent;
R7 and R8 combine with each other

or

to be. The method of claim 1,
The aryl having 6 to 30 carbon atoms or the heteroaryl having 5 to 60 carbon atoms may be selected from phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, oxadiazole, thiophenyl, Thiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzthiazole, carbazole, quinolinyl, isoquinoli An organic light emitting compound, characterized in that it is Neil, indole or pyrenyl. 3. The method of claim 2,
R1 and R3 are each independently a simple bond or a phenylene group;
R2 and R4 are each independently phenyl, naphthyl, pyridinyl, pyrimidinyl or triazinyl unsubstituted or substituted with one or more phenyl groups;
R5 and R6 are each independently a hydrogen atom, C1 ~ C5 linear or branched alkyl, or a phenyl group,
R5 and R6 combine with each other

or

X is absent or a simple bond, R9, R10 and R11 are each independently a C1 to C5 alkyl group or a phenyl group;
R7 and R8 are each independently a hydrogen atom or a straight or branched chain alkyl group of C1 ~ C5,
R7 and R8 combine with each other

or

An organic light emitting compound, characterized in that to form. The method of claim 3, wherein
The organic light emitting compound is an organic light emitting compound, characterized in that any one of compounds 1 to 42:

The method of claim 1,
The organic light emitting compound is an organic light emitting compound, characterized in that the phosphorescent green host material of the organic electroluminescent device material. An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,
Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of claim 1 singly or in combination of two or more. The method according to claim 6,
An organic electroluminescent device comprising the organic light emitting compound as a phosphorescent green host material. The method according to claim 6 or 7,
The organic electroluminescent device
An organic electroluminescent device comprising a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked in this order.