KR101529164B1 - New organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

Abstract

상기 유기발광화합물은 인광 녹색 호스트 물질로서 유기전기발광소자에 적용될 수 있으며, 이 경우 유기전기발광소자의 발광효율 및 소자 수명을 향상시킬 수 있다.The present invention provides an organic electroluminescent compound represented by the following Formula 1 and an organic electroluminescent device comprising the same:
[ Chemical Formula 1 ]

The organic luminescent compound may be applied to an organic electroluminescent device as a phosphorescent green host material. In this case, the luminescent efficiency and lifetime of the organic electroluminescent device can be improved.

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 including 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 luminescent materials to date, but the development of a phosphorescent material on the mechanism of electroluminescence is one of the best ways to improve the luminous efficiency up to 4 times theoretically. 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. Recently, many phosphorescent materials have been studied in Japan and Europe.

CBP is the most widely known host material for a phosphorescent light emitting material, and a high efficiency OLED using a hole blocking layer such as BCP and BAlq is known. In Pioneer Japan, a high performance OLED using a BAlq derivative as a host is known There is one.

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. Since the power efficiency in OLED = (π / voltage) × current efficiency, the power efficiency is inversely proportional to the voltage, and the power efficiency of the OLED should be high if the power consumption is low. OLEDs using real phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials. However, when conventional materials such as BAlq and CBP are used as hosts for phosphorescent materials, OLEDs using fluorescent materials (Lm / w) since the driving voltage is high. 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 to an organic luminescent compound which can lower a driving voltage when applied to an organic luminescent device and improve luminous efficiency, brightness, thermal stability, The purpose is 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]

In this formula,

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또는

이며, 상기에서 W는 질소원자, 산소원자, 황원자 또는 Si(C1~C5의 알킬)₂이며, R1은 각각 독립적으로 페닐, 피롤, 피라졸, 이미다졸, 트리아졸, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐 또는 나프틸기이며, W가 산소원자, 황원자 또는 Si(C1~C5의 알킬)₂인 경우에 R1은 부존재하며;X is

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or

Wherein W is a nitrogen atom, an oxygen atom, a sulfur atom or Si (C1 to C5 alkyl) ₂ , and each R1 is independently phenyl, pyrrole, pyrazole, imidazole, triazole, pyridinyl, pyrimidinyl, A pyridinyl, a pyridazinyl, a triazinyl or a naphthyl group, and when W is an oxygen atom, a sulfur atom or Si (C1-C5 alkyl) ₂ , R1 is absent;

Y is a nitrogen or carbon atom, and at least one of Y is a nitrogen atom;

n is 0 or 1;

R2 to R5 each independently represent a hydrogen atom, a C1 ~ C10 linear or branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10, CF ₃ or Si (CH _{3) 3,} or,

Heavy hydrogen atom, a linear or branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10 of _{C1 ~ C10, CF 3, Si} (CH 3) 3, phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrolyl At least one group selected from the group consisting of an alkyl group, an alkoxy group, an alkoxy group, an alkoxycarbonyl group, an alkoxycarbonyl group, an alkoxycarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms.

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 electroluminescent compound according to the present invention can be applied to an organic electroluminescent device as a phosphorescent green host material. When applied to an organic electroluminescent device, the electroluminescent compound lowers a driving voltage and improves luminous efficiency, brightness, thermal stability, and device lifetime.

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]

In this formula,

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또는

이며, 상기에서 W는 질소원자, 산소원자, 황원자 또는 Si(C1~C5의 알킬)₂이며, R1은 각각 독립적으로 페닐, 피롤, 피라졸, 이미다졸, 트리아졸, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐 또는 나프틸기이며, W가 산소원자, 황원자 또는 Si(C1~C5의 알킬)₂인 경우에 R1은 부존재하며;X is

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or

Wherein W is a nitrogen atom, an oxygen atom, a sulfur atom or Si (C1 to C5 alkyl) ₂ , and each R1 is independently phenyl, pyrrole, pyrazole, imidazole, triazole, pyridinyl, pyrimidinyl, A pyridinyl, a pyridazinyl, a triazinyl or a naphthyl group, and when W is an oxygen atom, a sulfur atom or Si (C1-C5 alkyl) ₂ , R1 is absent;

Y is a nitrogen or carbon atom, and at least one of Y is a nitrogen atom;

n is 0 or 1;

R2 to R5 each independently represent a hydrogen atom, a C1 ~ C10 linear or branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10, CF ₃ or Si (CH _{3) 3,} or,

Heavy hydrogen atom, a linear or branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10 of _{C1 ~ C10, CF 3, Si} (CH 3) 3, phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrolyl At least one group selected from the group consisting of an alkyl group, an alkoxy group, an alkoxy group, an alkoxycarbonyl group, an alkoxycarbonyl group, an alkoxycarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms.

The heteroaryl group having 6 to 30 carbon atoms or the heteroaryl group having 5 to 60 carbon atoms is preferably selected from phenyl, naphthyl, biphenyl, binaphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole, triazole , Oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzthiazole , Carbazole, quinolinyl, isoquinolinyl, indole or pyrenyl group.

More preferably,

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또는

이며, 상기에서 W는 질소원자, 산소원자, 황원자 또는 Si(CH₃)₂이며, R1은 각각 독립적으로 페닐, 피리디닐 또는 피리미디닐기이며, W가 산소원자, 황원자 또는 Si(CH₃)₂인 경우에 R1은 부존재하며;X is

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or

And, in the above W is a _second nitrogen atom, an oxygen atom, a sulfur atom, or Si (CH _3), R1 is independently a phenyl, a pyridinyl or pyrimidinyl group, W is an oxygen atom, a sulfur atom, or Si (CH _{3) 2,} respectively R1 is absent;

Y is a nitrogen or carbon atom, and at least one of Y is a nitrogen atom;

n is 0 or 1;

R2 to R5 may be hydrogen atoms.

The organic luminescent 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, the hole transport layer material may be at least one selected from the group consisting of bis (N- (1-naphthyl-n-phenyl)) benzidine (? -NPD), N, -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, the organic luminescent compound of the present invention may be used as a phosphorescent green host material in a case where the single luminescent material or the luminescent host material used in the luminescent layer material used is green. In addition, tris (8-hydroxyquinolinolato) aluminum ), Blue (Balq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl) series, Spiro ) Material, a spiro-DPVBi (spiro-4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazolyl) Lithium salts), bis (biphenylvinyl) benzene, aluminum-quinoline metal complexes, imidazole, thiazole and oxazole metal complexes.

Among the light emitting layer materials, IDE102 and IDE105 available from Idemitsu as phosphorescent dopants and tris (2-phenylpyridine) iridium (III) (Ir (ppy ) 3), iridium (III) bis [(4,6-difluorophenyl) pyridinate-N, C-2 '] picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys Platy (II) octaethylporphyrin (PtOEP), TBE002 (Cobion), etc. may 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]

50 g (151.5 mmol) of 1,4-bis (4,4,5,5-tetramethyl-1,3,2-dioxabororen-2-yl) benzene and 61.2 g (303 mmol) was dissolved in 500 mml of 1,4-dioxane and refluxed with 3.5 g (3.03 mmol) of tetrakis (triphenylphosphine) palladium, 31.4 g (227.25 mmol) of calcium carbonate and 50 ml of purified water under nitrogen flow for 12 hours Lt; / RTI > After completion of the reaction, slowly cool to room temperature and pour into purified water to solidify. The filtered solid was washed with purified water and methanol to obtain 34.9 g (72%) of intermediate compound [I-1] in a yellow solid state.

Preparation of intermediate compounds [1-2], [1-3]

34 g (106.15 mmol) of the intermediate compound [1-1] was dissolved in 55.6 g (212.3 mmol) of triphenylphosphine and 500 ml of 1,2-dichlorobenzene in a nitrogen atmosphere, and the mixture was stirred at 180 ° C for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water and ethyl acetate were added, and the organic layer was collected by layer separation. The organic layer is dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to obtain 11.4 g (42%) of intermediate compound [1-2] in the off-white solid state and 12.2 g (45%) of [1-3] in the form of a pale solid.

Preparation of intermediate compound [1-4]

(42.91 mmol) of the intermediate compound [1-2] and 8.6 ml (85.83 mmol) of bromobenzene were dissolved in 250 mml of toluene, and 96 mg (0.42 mmol) of palladium (II) 20.9 g (64.36 mmol) of carbonate are added. After stirring at room temperature, 0.41 ml (0.85 mmol) of tri-t-butylphosphine was added dropwise, and the mixture was stirred under reflux while gradually raising the reaction temperature. When the reaction is complete, dilute with 1 L of ethyl acetate and extract with 1 L of saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and recrystallized from dichloromethane and methanol to obtain 9.6 g (68%) of an off-white solid intermediate compound [1-4]

Preparation of intermediate compound [1-5]

In a round bottom flask, 40 g (97.05 mmol) of 4,4'-dibromo-1,1'-binaphthalene was dissolved in 2 L of anhydrous tetrahydrofuran in a nitrogen atmosphere, 42.7 ml (2.5 M) of n-butyl lithium (106.67 mmol) is added dropwise. At the same temperature, 25.9 g (97.05 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was added and the temperature was gradually raised to room temperature. Distilled water and ethyl acetate are added at room temperature, and the organic layer is collected by layer separation. The organic layer is dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to obtain 27.9 g (51%) of intermediate compound [1-5] in the form of white solid through column chromatography.

Preparation of compound [1]

A round bottom flask was charged with 5 g (15.04 mmol) of intermediate compound [1-4], 10.1 g (18.05 mmol) of intermediate compound [1-4], 2.86 g (45.12 mmol) of copper powder, 6.23 g 100 ml of xylene is added, and the mixture is stirred under reflux in a nitrogen atmosphere. After completion of the reaction, distilled water and ethyl acetate are added at room temperature, and the organic layer is collected by layer separation. The organic layer is dried over anhydrous magnesium sulfate and filtered. Recrystallization from dichloromethane and methanol gave 7.6 g (62%) of the desired compound [1] as a off-white solid.

Preparation of compound [8]

[Reaction Scheme 2]

Preparation of intermediate compound [8-1]

In the same manner as in Reaction Scheme 1, 20 g (104.73 mmol) of 1,4-dichloro-2-nitrobenzene, 27.9 g (12.56 mmol) of phenanthrene-9-ylboronic acid, 2.42 g of tetrakis (triphenylphosphine) palladium 21.6 g (62%) of intermediate compound [8-1] as white solid was obtained using 21.7 g (157.09 mmol) of calcium carbonate, 1,4-dioxane and purified water.

Preparation of intermediate compound [8-2]

Using Intermediate Compound [8-1] (21 g, 62.91 mmol), triphenylphosphine (33 g, 125.83 mmol) and 1,2-dichlorobenzene, the title compound was obtained as a white solid ] (18.6 g, 68%).

Preparation of intermediate compound [8-3]

(59.64 mmol) of intermediate compound [8-3], 13.3 ml (119.29 mmol) of iodobenzene, 267 mg (1.19 mmol) of palladium (II) acetate and 29.1 g (89.64 mmol) of cesium carbonate in the same manner as in Scheme 1, , 14.4 g (64%) of intermediate compound [8-3] in yellow solid state was obtained using toluene.

Preparation of intermediate compound [8-4]

, 7.4 g (44.46 mmol) of (2-nitrophenyl) boronic acid and 856 mg (0.74 mmol) of tetrakis (triphenylphosphine) palladium were added to a solution of the intermediate compound [8-3] 12.3 g (72%) of intermediate compound [8-4] in white solid state was obtained using 7.6 g (55.57 mmol) of calcium carbonate, 1,4-dioxane and purified water.

Preparation of intermediate compounds [8-5], [8-6]

Using intermediate compound [8-4] in an amount of 12 g (25.83 mmol), triphenylphosphine (13.5 g, 51.66 mmol) and 1,2-dichlorobenzene, an intermediate compound [8-5 ] Of 4.6 g (40%), and [8.6] of 4.9 g (42%).

Preparation of compound [8]

4.5 g (10.4 mmol) of intermediate compound [8-6], 7 g (12.48 mmol) of intermediate compound [1-5], 1.9 g (30.12 mmol) of copper powder and 4.1 g ) And 6.7 g (71%) of the desired compound [8] as a off-white solid were obtained using xylene.

Preparation of compound [17]

[Reaction Scheme 3]

Preparation of intermediate compound [17-1]

In the same manner as in Scheme 1, 50 g (255.04 mmol) of 6-bromo-1H-indole, 57 ml (510.09 mmol) of iodobenzene, 1.14 g (5.10 mmol) of palladium (II) acetate, 124.6 g (382.56 mmol) , And 47.1 g (68%) of intermediate compound [17-1] as a white solid state was obtained using toluene.

Preparation of intermediate compound [17-2]

(207.5 mmol) of intermediate compound [17-1], 34.5 g (207.2 mmol) of (2-nitrophenyl) boronic acid and 3.99 g (3.45 mmol) of tetrakis (triphenylphosphine) palladium in the same manner as in Scheme 1, 38.5 g (71%) of a white solid intermediate compound [17-2] was obtained using 35.8 g (259.05 mmol) of calcium carbonate, 1,4-dioxane and purified water.

Preparation of intermediate compounds [17-3], [17-4]

17.5 g (122.47 mmol) of intermediate compound [17-2], 64.2 g (244.95 mmol) of triphenylphosphine and 1,2-dichlorobenzene were used in the same manner as in Scheme 1 to obtain intermediate compound [17-3 14.1 g (41%) of [17-4] and 14.5 g (42%) of [17-4].

Preparation of compound [17]

In the same manner as in Scheme 1, 4 g (14.16 mmol) of the intermediate compound [17-3], 9.6 g (17 mmol) of the intermediate compound [1-5], 2.69 g (42.48 mmol) of copper powder, 5.8 g ) And using xylene, 7.2 g (67%) of the desired compound as a off-white solid [17] was obtained.

Compounds of compounds 1 to 60 were prepared according to the methods of Schemes 1 to 3 above and the results are shown below in the second group of tablets.

[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

Wherein the compound represented by the following formula (a) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq ₃ (30 nm) / LiF (30 nm) / compound (30 nm) / compound a + compound 30 nm / ITO / 2-TNATA 0.5 nm) / Al (60 nm).

An anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate into 50 mm × 50 mm × 0.7 mm size, ultrasonically cleaning it in acetone, isopropyl alcohol and pure water for 15 minutes each, Ozone was cleaned and used. 2-TNATA was vacuum deposited on the substrate to form a 80 nm thick princess grain 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 Formula (a) and a compound represented by Formula (c) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq ₃ compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injecting layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in Table 3. [ This is referred to as Comparative Sample 1.

Comparative Example 2

Wherein the compound represented by the following formula (b) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq ₃ (30 nm) / LiF (30 nm) / compound (30 nm) / compound (30 nm) / ITO / 2-TNATA 0.5 nm) / Al (60 nm).

An anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate into 50 mm × 50 mm × 0.7 mm size, ultrasonically cleaning it in acetone, isopropyl alcohol and pure water for 15 minutes each, Ozone was cleaned and 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 Formula (a) and a compound represented by Formula (c) (doping ratio: 10%) were vacuum-deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq ₃ compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injecting layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to produce an organic light emitting device as shown in Table 3. This is referred to as Comparative Sample 2.

Examples 1-56.

In the same manner as in Comparative Example 1 except that the phosphorescent host compound a was used instead of the phosphorescent host compound a shown in the above Synthesis Example in Comparative Example 1, ITO / 2-TNATA (30 nm) / Alq ₃ (30 nm) / LiF (0.5 nm) / Al (30 nm) / alpha -NPD (30 nm) / [phosphorescent green host compound 1-60 or compound c 60 nm) was fabricated. These are referred to as Samples 1 to 60, respectively.

Evaluation Example 1: Evaluation of luminescence characteristics of Comparative Samples 1 and 2 and Samples 1 to 60

The emission luminance, the luminous efficiency and the emission peak were evaluated using Keithleysourcemeter "2400" and KONIKA MINOLTA "CS-2000" for Comparative Samples 1 and 2 and Samples 1 to 56, Group)]. The samples showed green emission peak values in the 511 to 517 nm range.

[Group 3]

Samples 1 to 60 exhibited improved luminescence characteristics as compared to Comparative Samples 1 and 2, as confirmed from the above [third group (group)].

Evaluation Example 2: Evaluation of life characteristics of Comparative Samples 1 and 2 and Samples 1 to 60

The comparative samples 1 and 2 and the samples 1 to 60 were measured for time to reach 97% on the basis of 3000 nits by using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in the following [ (Group)].

[Group 4]

Samples 1 to 56 showed improved lifespan characteristics as compared to Comparative Samples 1 and 2, as confirmed from [fourth set of group (s)].

Claims (8)

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

In this formula,
X is

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

Wherein W is a nitrogen atom, an oxygen atom, a sulfur atom or Si (C1 to C5 alkyl) ₂ , and each R1 is independently phenyl, pyrrole, pyrazole, imidazole, triazole, pyridinyl, pyrimidinyl, A pyridinyl, a pyridazinyl, a triazinyl or a naphthyl group, and when W is an oxygen atom, a sulfur atom or Si (C1-C5 alkyl) ₂ , R1 is absent;
Y is a nitrogen or carbon atom, and at least one of Y is a nitrogen atom;
n is 1;
R2 to R5 each independently represent a hydrogen atom, a C1 ~ C10 linear or branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10, CF ₃ or Si (CH _{3) 3,} or,
Heavy hydrogen atom, a linear or branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10 of _{C1 ~ C10, CF 3, Si} (CH 3) 3, phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrolyl At least one group selected from the group consisting of an alkyl group, an alkoxy group, an alkoxy group, an alkoxycarbonyl group, an alkoxycarbonyl group, an alkoxycarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms. The method according to claim 1,
The heteroaryl group having 6 to 30 carbon atoms or the heteroaryl group having 5 to 60 carbon atoms is preferably selected from phenyl, naphthyl, biphenyl, binaphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, Benzothiazole, benzothiazole, carbazole, benzothiazole, thiadiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, Quinolinyl, quinolinyl, isoquinolinyl, indole or pyrenyl. 3. The method of claim 2,
X is

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

And, in the above W is a _second nitrogen atom, an oxygen atom, a sulfur atom, or Si (CH _3), R1 is independently a phenyl, a pyridinyl or pyrimidinyl group, W is an oxygen atom, a sulfur atom, or Si (CH _{3) 2,} respectively R1 is absent;
Y is a nitrogen or carbon atom, and at least one of Y is a nitrogen atom;
n is 1;
And R 2 to R 5 are hydrogen atoms. The method of claim 3,
Wherein the organic light emitting compound is any one of compounds 1-25, 29-53, and 55-60.

The method according to claim 1,
Wherein the organic light emitting compound is a phosphorescent green host material in a material for an organic electroluminescence device. 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,
Wherein the organic electroluminescent compound is contained as a phosphorescent green host material. 8. The method according to claim 6 or 7,
The organic electroluminescent device
Wherein the anode, the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron injecting layer, and the cathode are stacked in this order.