KR101600434B1 - 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. Because OLEDs have power efficiency = (π / voltage) ㅧ current efficiency, the power efficiency is inversely proportional to the voltage. 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 =

[ 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, A 및 B는 각각 독립적으로 탄소원자 또는 질소원자이며;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, R 1 is absent when A is an oxygen atom, sulfur atom or Si (C1 to C5 alkyl) ₂ , A and B are each independently a carbon atom or a nitrogen atom ;

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

Z is a simple bond or absent;

R2 and R3 are each independently a hydrogen atom, a C1 ~ C10 straight chain alkyl, C3 ~ C10 branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10, CF ₃ or Si (CH _{3) 3,} or,

A heavy hydrogen atom, C1 ~ C10 straight chain alkyl, C3 ~ C10 branched alkyl, alkoxy of C1 ~ C10, halogen, _{nitrile, CF 3, Si (CH 3} ) 3, phenyl, biphenyl, naphthyl, phenanthrenyl, A group consisting of a fluorenyl, a pyrrole, a pyrazole, an imidazole, a triazole, an oxazole, an oxadiazole, a thiophenyl, a thiazole, a thiadiazole, a pyrazinyl, a pyridazinylpyridinyl, a pyrimidinyl and a triazinyl 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)

[ 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, A 및 B는 각각 독립적으로 탄소원자 또는 질소원자이며;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, R 1 is absent when A is an oxygen atom, sulfur atom or Si (C1 to C5 alkyl) ₂ , A and B are each independently a carbon atom or a nitrogen atom ;

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

Z is a simple bond or absent;

R2 and R3 are each independently a hydrogen atom, a C1 ~ C10 straight chain alkyl, C3 ~ C10 branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10, CF ₃ or Si (CH _{3) 3,} or,

A heavy hydrogen atom, C1 ~ C10 straight chain alkyl, C3 ~ C10 branched alkyl, alkoxy of C1 ~ C10, halogen, _{nitrile, CF 3, Si (CH 3} ) 3, phenyl, biphenyl, naphthyl, phenanthrenyl, A group consisting of a fluorenyl, a pyrrole, a pyrazole, an imidazole, a triazole, an oxazole, an oxadiazole, a thiophenyl, a thiazole, a thiadiazole, a pyrazinyl, a pyridazinylpyridinyl, a pyrimidinyl and a triazinyl group A substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms.

Preferably, the aryl of 6 to 30 carbon atoms or the heteroaryl of 5 to 60 carbon atoms is 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 페닐기이며, W가 산소원자, 황원자 또는 Si(CH₃)₂인 경우에 R1은 부존재하며, A 및 B는 각각 독립적으로 탄소원자 또는 질소원자이며;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 a phenyl group, and R1 is absent, and if W is an oxygen atom, a sulfur atom, or Si (CH _{3) 2,} A and B are each independently a carbon atom or a nitrogen atom;

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

Z is a simple bond or absent;

R2 and R3 are 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 of lithium (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.

Synthesis of Compound [1]

[Reaction Scheme 1]

Preparation of intermediate compound [1-1]

In a 250 mL reaction flask, 10.0 g (21.09 mmol) of 2,7-dibromo-9,9'-spiro [fluorene], 11-phenyl-11,12-dihydroindolo [2,3- (31.63 mmol) of sodium tert-butoxide were added and the mixture was poured into a nitrogen stream Was stirred under reflux for 12 hours with 100 mL of toluene. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 7.2 g (47%) of intermediate compound [1-1] as a white solid.

7.0 g (0.219 mol) of [1-1] and 150 ml of anhydrous tetrahydrofuran were placed in a two-neck flask, and the mixture was stirred at -78 ° C. 4.24 mL (10.61 mmol) of n-butyllithium (2.5 M in hexane) is added dropwise at this temperature and after 30 minutes 1.18 ml (10.61 mmol) of trimethylborate are added. The organic layer was separated, dried over anhydrous magnesium sulfate, and then filtered. The organic layer was concentrated under reduced pressure, and recrystallized from dichloromethane and hexane to obtain an intermediate compound of white solid 3.4 g (51%) of [1-2] was obtained.

Preparation of compound [1]

To the reaction flask were added 3.4 g (4.92 mmol) of the intermediate compound [1-2], 1.45 g (5.41 mmol) of 2-chloro-4,6-diphenyl- 57 mg (0.05 mmol) of palladium and 1.02 g (7.38 mmol) of potassium carbonate (K ₂ CO ₃ ) were added and stirred under reflux for 12 hours with 100 mL of 1,4-dioxane and 10 mL of purified water under a nitrogen stream. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid was washed with purified water and methanol, and recrystallized from dichloromethane and methanol to give 2.9 g (68%) of a white solid compound [1].

Synthesis of Compound [25]

[Reaction Scheme 2]

Preparation of compound [25]

 The objective compound [25] was synthesized by proceeding in the same manner as the compound [1].

Compounds 1-6 and 8-74 were prepared according to the methods of Schemes 1 and 2 above and the results are shown below.

[ Synthetic example  1] Synthesis of Compound [1]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 2H), 8.18 (d, 4H), 8.02 (d, 1H), 7.84 ~ 7.77 (m, 4H), 7.65 (d, 2H), 7.53 ~ 7.06 (m, 26H)

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  2] Synthesis of compound [2]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.18 (d, 4H), 8.02 (d, 1H), 7.84 ~ 7.77 (m, 3H), 7.65 (d, 2H), 7.53 ~ 7.06 (m, 28H)

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  3] Synthesis of compound [3]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 2H), 8.18 (d, 4H), 8.02 (d, 1H), 7.84 ~ 7.77 (m, 4H), 7.65 (d, 2H), 7.53 ~ 7.06 (m, 26H)

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  4] Synthesis of compound [4]

^{1 H NMR (300 MHz, CDCl} 3): δ 9.41 (s, 1H), 8.64 (d, 1H), 8.45 (d, 1H), 8.18 (d, 4H), 7.84 ~ 7.77 (m, 4H), 7.65 (d, 2H), 7.53 ~ 7.06 (m, 25H)

MS / FAB: 879 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  5] Synthesis of compound [5]

^{1 H NMR (300 MHz, CDCl} 3): δ 9.41 (s, 1H), 8.64 (d, 1H), 8.45 (d, 1H), 8.18 (d, 4H), 7.84 ~ 7.77 (m, 4H), 7.65 (d, 2H), 7.53 ~ 7.06 (m, 25H)

MS / FAB: 879 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  6] Synthesis of compound [6]

^{1 H NMR (300 MHz, CDCl} 3): δ 9.61 (s, 1H), 8.84 (s, 1H), 8.65 (s, 1H), 8.38 (s, 4H), 8.04 ~ 7.97 (m, 4H), 7.85 (s, 2H), 7.61 ~ 7.26 (m, 25H)

MS / FAB: 879 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  8] Synthesis of compound [8]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.65 (s, 2H), 8.38 (s, 4H), 8.22 (s, 1H), 8.04 ~ 7.97 (m, 4H), 7.85 (s, 2H), 7.68 ~ 7.26 (m, 26H)

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  9] Synthesis of compound [9]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.38 (s, 4H), 8.03-7.97 (m, 4H), 7.85-7.82

(M, 2H), 2.45 (s, 3H)

MS / FAB: 880 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  10] Synthesis of compound [10]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.38 (s, 4H), 8.03-7.97 (m, 4H), 7.85-7.82 (m, 4H), 7.68-7.45 m, SH), 6.95 (t, 2H), 2.39 (s, 6H)

MS / FAB: 882 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  11] Synthesis of compound [11]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.18 (d, 4H), 8.04 (d, 1H), 7.83 ~ 7.77 (m, 3H), 7.65 (d, 2H), 7.53 ~ 7.06 (m, 24H), 2.19-2.18 (m, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 856 (M ⁺ )

[ Synthetic example  12] Synthesis of compound [12]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.33 (d, 1H), 8.18 (m, 4H), 7.84 ~ 7.77 (m, 4H), 7.65 (d, 2H), 7.53 ~ 7.06 (m, 24H), 6.42 (d, IH)

MS / FAB: 827 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  13] Synthesis of Compound [13]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.45 (d, 1 H), 8.18 (d, 4H), 7.84-7.77 2H), 2.95 (m, 2H), 7.05 (m, 2H)

MS / FAB: 829 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  14] Synthesis of compound [14]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.33 (d, 1H), 8.18 (m, 4H), 7.84 ~ 7.77 (m, 4H), 7.65 (d, 2H), 7.50 ~ 7.06 (m, 24H), 6.42 (d, IH)

MS / FAB: 827 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  15] Synthesis of compound [15]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.18 (d, 4H), 7.84 ~ 7.77 (m, 4H), 7.65 (d, 2H), 7.53 ~ 7.23 (m, 17H), 7.09 ~ 7.06 (m, 2H), 6.01 (s, 1H), 2.04 (s, 3H), 1.94 (s, 3H)

MS / FAB: 832 (M ^< ^{+ &} gt ^; ) [

[ Synthetic example  16] Synthesis of compound [16]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.18 (m, 4H), 7.83-7.77 (m, 4H), 7.65 (m, 2H), 7.53-7.25 2H), 6.38 (d, 1 H), 6.31 (t, 1 H)

MS / FAB: 804 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  17] Synthesis of compound [17]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.35 (d, 1H), 8.28 (m, 4H), 7.95 ~ 7.74 (m, 5H), 7.65 (m, 2H), 7.50 ~ 7.15 (m, 21H)

MS / FAB: 819 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  18] Synthesis of compound [18]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.35 (d, 1H), 8.18 (m, 4H), 7.98 (d, 1H), 7.88 ~ 7.65 (m, 7H), 7.53 (d, 1 H), 7.41-7.15 (m, 19 H)

MS / FAB: 819 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  19] Synthesis of compound [19]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.45 (d, IH), 8.35 (d, IH), 8.18 (m, 4H), 7.88-7. (d, 1 H), 7.46-7.15 (m, 19 H)

MS / FAB: 819 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  20] Synthesis of compound [20]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.18 (m, 5H), 7.88 ~ 7.76 (m, 5H), 7.65 (m, 2H), 7.51 ~ 7.15 (m, 21H) , 0.56 (s, 6H)

MS / FAB: 845 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  21] Synthesis of Compound [21]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 (d, 1H), 8.27 (d, 4H), 7.93-7.86 (m, 5H), 7.74-7.71 21H), 0.65 (s, 6H)

MS / FAB: 845 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  22] Synthesis of compound [22]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.54 (d, 1H), 8.27 (d, 4H), 7.93 ~ 7.86 (m, 5H), 7.74 (d, 2H), 7.65 ~ 7.15 (m, 22H) ,

MS / FAB: 802 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  23] Synthesis of compound [23]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.54 (d, 1H), 8.27 (d, 4H), 8.15 (d, 2H), 8.04 (d, 1H), 7.93 ~ 7.85 (m, 4H), 7.77 ~ 7.15 (m, 24H)

MS / FAB: 869 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  24] Synthesis of compound [24]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.44 (d, 1H), 8.27 (d, 4H), 8.15 (d, 2H), 8.04 ~ 7.86 (m, 4H), 7.74 ~ 7.33 (m, 20H) , 7.18-7.15 (m, 5H)

MS / FAB: 869 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  25] Synthesis of compound [25]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.54 (d, 2H), 8.27 (d, 4H), 8.11 (d, 1H), 7.93 ~ 7.74 (m, 6H), 7.57 ~ 7.06 (m, 26H)

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  26] Synthesis of compound [26]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 (m, 1H), 8.27 (m, 4H), 8.11

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  27] Synthesis of Compound [27]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 (m, 2H), 8.27 (m, 4H), 8.11

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  28] Synthesis of compound [28]

¹ H NMR (300 MHz, CDCl ₃ ):? 9.50 (m, IH), 8.73 (m, IH), 8.54 ~ 7.18 (m, 25H)

MS / FAB: 879 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  29] Synthesis of compound [29]

¹ H NMR (300 MHz, CDCl ₃ ):? 9.50 (m, IH), 8.73 (m, IH), 8.54 (m, 25H)

MS / FAB: 879 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  30] Synthesis of compound [30]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 to 8.53 (m, 4H), 8.27 (m, 4H), 7.86-7.24

MS / FAB: 928 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  31] Synthesis of Compound [31]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.55 (d, 2H), 8.28 (d, 4H), 8.12 (d, 1H), 7.94 ~ 7.75 (m, 6H), 7.58 ~ 7.07 (m, 26H)

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  32] Synthesis of Compound [32]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.28 (d, 4H), 7.93 ~ 7.72 (m, 8H), 7.51 ~ 7.34 (m, 18H), 7.19 ~ 7.07 (m, 5H), 6.85 (t, 2H), 2.81 (s, 4H)

MS / FAB: 880 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  33] Synthesis of compound [33]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.28 (d, 4H), 7.93-7.72 (m, 8H), 7.58-7.34 (m, 18H), 7.19-7.07 2H), 2.29 (s, 6H)

MS / FAB: 882 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  34] Synthesis of compound [34]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.28 (d, 4H), 7.94 ~ 7.75 (m, 8H), 7.58 ~ 7.33 (m, 18H), 7.19 ~ 7.07 (m, 5H), 6.87 (t, 2H), [delta] 6.80 (s, 2H)

MS / FAB: &^lt; / RTI ^& gt ^; 854 (M ⁺ )

[ Synthetic example  35] Synthesis of Compound [35]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.55 (d, 1H), 8.28 (d, 4H), 8.14 (d, 1H), 7.94 ~ 7.75 (m, 5H), 7.59 ~ 7.07 (m, 24H) , 2.29 (d, 6H)

MS / FAB: &^lt; / RTI ^& gt ^; 856 (M ⁺ )

[ Synthetic example  36] Synthesis of Compound [36]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.33 (d, 1H), 8.18 (m, 4H), 7.84 ~ 7.65 (m, 6H), 7.50 ~ 7.07 (m, 24H) , 6.42 (d, 1 H)

MS / FAB: 828 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  37] Synthesis of Compound [37]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.45 (d, 1H), 8.18 (m, 4H), 7.84-7.65 , 4.04 (t, 2 H), 2.95 (t, 2 H)

MS / FAB: 830 (M ^< ^{+ &} gt ^; ) [

[ Synthetic example  38] Synthesis of Compound [38]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.33 (d, 1H), 8.18 (m, 4H), 7.84 ~ 7.65 (m, 6H), 7.50 ~ 7.06 (m, 24H) , 6.42 (t, 1 H)

MS / FAB: 828 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  39] Synthesis of compound [39]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.18 (m, 4H), 7.84-7.65 (m, 6H), 7.48-7.33 (m, 17H), 7.09-7. 1H), 6.77 (s, 3H), 6.94 (s, 1H)

MS / FAB: 832 (M ^< ^{+ &} gt ^; ) [

[ Synthetic example  40] Synthesis of compound [40]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.18 (m, 4H), 7.84 ~ 7.65 (m, 6H), 7.48 ~ 7.06 (m, 23H), 6.77 (t, 1H), 6.70 (s, 1H) , 6.48 (d, 1 H), 6.31 (t, 1 H)

MS / FAB: 804 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  41] Synthesis of compound [41]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.35 (d, 1H), 8.18 (d, 4H), 7.95 ~ 7.65 (m, 7H), 7.50 ~ 7.06 (m, 21H)

MS / FAB: 818 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  42] Synthesis of compound [42]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.35 (d, 1H), 8.18 (d, 4H), 7.98 (d, 1H), 7.88 ~ 7.65 (m, 7H), 7.42 ~ 7.07 (m, 20H)

MS / FAB: 818 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  43] Synthesis of compound [43]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.35 (d, 1H), 8.18 (d, 4H), 7.88 ~ 7.65 (m, 8H), 7.42 ~ 7.07 (m, 20H)

MS / FAB: 818 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  44] Synthesis of compound [44]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.18 (d, 5H), 7.84 ~ 7.65 (m, 7H), 7.51 ~ 7.07 (m, 21H), 0.56 (s, 6H)

MS / FAB: 845 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  45] Synthesis of compound [45]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.18 (d, 4H), 7.84 ~ 7.65 (m, 8H), 7.42 ~ 7.07 (m, 21H), 0.56 (s, 6H)

MS / FAB: 845 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  46] Synthesis of Compound [46]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.18 (d, 4H), 7.83 ~ 7.65 (m, 7H), 7.56 (d, 1H), 7.47 ~ 7.22 (m, 21H) ,

MS / FAB: &^lt; / RTI ^& gt ^; 802.92 (M ⁺ )

[ Synthetic example  47] Synthesis of compound [47]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.18 (d, 4H), 8.06 (m, 2H), 7.95 (d, 1H), 7.84 ~ 7.06 (m, 28H)

MS / FAB: 869.04 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  48] Synthesis of Compound [48]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.35 (m, 1H), 8.18 (d, 4H), 8.06 (m, 2H), 7.95 ~ 7.88 (m, 2H), 7.77 ~ 7.25 (m, 22H) , 7.09 ~ 6.97 (m, 5H)

MS / FAB: 869.04 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  49] Synthesis of Compound [49]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 ~ 8.42 (m, 4H), 8.18 (d, 4H), 8.02 (d, 1H), 7.94 ~ 7.77 (m, 4H), 7.48 ~ 7.14 (m, 28H)

MS / FAB: 880.04 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  50] Synthesis of Compound [50]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 2H), 8.18 (d, 4H), 8.02 ~ 7.99 (m, 2H), 7.84 ~ 7.77 (m, 4H), 7.69 (d, 1H) , 7.48 ~ 7.14 (m, 27H), 6.97 (m, IH)

MS / FAB: 880.04 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  51] Synthesis of Compound [51]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 to 8.51 (m, 3H), 8.28 (m, 4H), 8.11 30H)

MS / FAB: 880 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  52] Synthesis of compound [52]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 to 8.51 (m, 3H), 8.28 (m, 4H), 8.11 , 7.62 ~ 7.24 (m, 29H), 7.28 (m, IH)

MS / FAB: 880 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  53] Synthesis of compound [53]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.54 (m, 1H), 8.27 (m, 4H), 8.11 ~ 8.08 (m, 2H), 7.86 ~ 7.27 (m, 3H), 7.24 ~ 7.57 (m, 28H), 7.10 ~ 7.06 (m, 2H)

MS / FAB: 880 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  54] Synthesis of compound [54]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 (m, 2H), 8.27 (m, 4H), 8.11

MS / FAB: 880 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  55] Synthesis of Compound [55]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 (m, 1H), 8.27 (m, 4H), 8.11

MS / FAB: 880 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  56] Synthesis of compound [56]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.54 ~ 8.48 (m, 2H), 8.27 (m, 4H), 7.93 ~ 7.86 (m, 3H), 7.62 (m, 1H), 7.55 ~ 7.10 (m, 2H), 6.90 (m, 1H), 6.80-6.72 (m, 3H), 6.62

MS / FAB: 908 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  57] Synthesis of compound [57]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 2H), 8.20 (d, 2H), 8.10 ~ 7.97 (m, 5H), 7.86 ~ 7.77 (m, 4H), 7.65 (d, 2H) , 7.48 ~ 7.06 (m, 26H)

MS / FAB: 876 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  58] Synthesis of Compound [58]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 2H), 8.20 (d, 4H), 8.10 (s, 2H), 8.02 (d, 1H), 7.84 ~ 7.77 (m, 4H), 7.65 (d, 2H), 7.53 ~ 7.35 (m, 14H), 7.25 ~ 7.07 (m, 12H)

MS / FAB: 876 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  59] Synthesis of Compound [59]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.45 (d, 2H), 8.13 (s, IH), 8.02 (d, IH), 7.84-7.69

MS / FAB: 877 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  60] Synthesis of Compound [60]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.20 (m, 2H), 8.10 ~ 8.02 (m, 5H), 7.86 ~ 7.77 (m, 3H), 7.65 (d, 2H) , 7.53 ~ 7.06 (m, 28H)

MS / FAB: 876 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  61] Synthesis of Compound [61]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.20 (m, 4H), 8.10 ~ 8.02 (m, 3H), 7.86 ~ 7.77 (m, 3H), 7.65 (d, 2H) , 7.53 ~ 7.06 (m, 28H)

MS / FAB: 876 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  62] Synthesis of Compound [62]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.13 (s, 1H), 8.02 (d, 1H), 7.83 ~ 7.65 (m, 9H), 7.53 ~ 7.06 (m, 28H)

MS / FAB: 877 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  63] Synthesis of Compound [63]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.54 (m, 1H), 8.44 (m, 1H), 8.29 (m, 2H), 8.19 ~ 8.06 (m, 5H), 7.97 ~ 7.86 (m, 4H) , 7.79 ~ 7.74 (m, 3H), 7.53 ~ 7.18 (m, 20H)

MS / FAB: 817 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  64] Synthesis of compound [64]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 (m, IH), 8.44 (m, IH), 8.29 (m, 7H), 7.53-7.46 (m, 10H), 7.34-7.18 (m, 10H)

MS / FAB: 817 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  65] Synthesis of compound [65]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 (m, IH), 8.44 (m, IH), 8.22 (m, 1 H), 7.55-7.18 (m, 19 H)

MS / FAB: 817 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  66] Synthesis of compound [66]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.54 (d, 1H), 8.44 (d, 1H), 8.29 (d, 2H), 8.19 ~ 8.06 (m, 4H), 7.97 ~ 7.85 (m, 5H) , 7.77 ~ 7.74 (m, 3H), 7.53 ~ 7.15 (m, 20H)

MS / FAB: 817 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  67] Synthesis of compound [67]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.54 (m, 1H), 8.44 (m, 1H), 8.29 (m, 4H), 8.19 (s, 2H), 7.97 ~ 7.85 (m, 5H), 7.77 (M, 3H), 7.62-7.46 (m, 10H), 7.34-7.15 (m, 10H)

MS / FAB: 817 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  68] Synthesis of compound [68]

¹ H NMR (300 MHz, CDCl ₃ ):? 8.54 (m, IH), 8.44 (m, IH), 8.22 (s, IH), 7.97-7.74 ~ 7.15 (m, 19H)

MS / FAB: 817 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  69] Synthesis of compound [69]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 2H), 8.20 (m, 2H), 8.10 (s, 2H), 8.02 ~ 7.98 (m, 2H), 7.84 ~ 7.74 (m, 6H) , 7.65 (d, IH), 7.47-7.31 (m, 14H), 7.25-7.06 (m,

MS / FAB: 876 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  70] Synthesis of compound [70]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.13 (s, 1H), 8.02 (d, 1H) 7.84 ~ 7.65 (m, 9H), 7.53 ~ 7.30 (m, 17H), 7.25 - 7.06 (m, 10 H), 6.97 (t, 1 H)

MS / FAB: 877 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  71] Synthesis of compound [71]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.45 (d, 1H), 8.20 (m, 4H), 8.10 (s, 2H), 8.02 (d, 1H) 7.84 (d, 1H), 7.77 (d, 2H), 7.53-7.28 (m, 19H), 7.23-7.13 (m, 13H)

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  72] Synthesis of compound [72]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.55 (d, 2H), 8.30 (m, 2H), 8.20 ~ 8.07 (m, 5H), 7.94 ~ 7.87 (m, 4H), 7.57 ~ 7.11 (m, 30H)

MS / FAB: 878 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  73] Synthesis of compound [73]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.55 (d, 1H), 8.23 (s, 1H), 8.12 (d, 1H), 7.94 ~ 7.79 (m, 7H), 7.63 ~ 7.11 (m, 32H)

MS / FAB: 879 (M ^< ^{+ &} gt ^; ).

[ Synthetic example  74] Synthesis of compound [74]

^{1 H NMR (300 MHz, CDCl} 3): δ 8.55 (d, 1H), 8.49 (s, 1H), 8.23 (s, 1H), 7.94 ~ 7.79 (m, 7H), 7.63 (d, 1H), 7.53 (M, 2H), 6.91 (t, 1H), 6.81-6.73 (m, 3H)

MS / FAB: &^lt; / RTI ^& gt ^; 907 (M ⁺ )

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  One.

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 2. This is referred to as Comparative Sample 2.

Example 1 ~ 73.

In the same manner as in Comparative Example 1 except that the phosphorescent host compound a in the above-mentioned synthesis example was used as a phosphorescent green host compound in the above Comparative Example 1, ITO (30 nm) / Alq ₃ (30 nm) / 2-TNATA (80 nm) /? -NPD (30 nm) / [phosphorescent green host compound 1-6 and one of 8-74 + compound c An organic light emitting device having a structure of LiF (0.5 nm) / Al (60 nm) was manufactured. These are referred to as Samples 1-6 and 8-74, respectively.

Evaluation example 1 : Comparative Sample 1 , 2 and samples 1-6 and 8-74

The luminescence brightness, the luminescence efficiency and the luminescence peak were evaluated using Keithleysourcemeter "2400" and KONIKA MINOLTA "CS-2000" for Comparative Samples 1 and 2 and Samples 1-6 and 8-74, Second group (group)]. The samples showed green emission peak values in the 511 to 517 nm range.

[Second group (group)]

Samples 1-6 and 8-74 exhibited improved luminescence properties as compared to Comparative Samples 1 and 2, as confirmed from [second set of group (s)].

Evaluation example  2: Evaluation of life characteristics of Comparative Samples 1 and 2 and Samples 1-6 and 8-74

For Comparative Samples 1 and 2 and Samples 1-6 and 8-74, the time to reach 97% of life on the basis of 3000 nits was measured using an LVS-1004AC life measuring device manufactured by ENC technology, Is shown in the following [third group (group)].

[Group 3]

 Samples 1-6 and 8-74 exhibited improved lifespan characteristics as compared to Comparative Samples 1 and 2, as confirmed from [third set of group (s)].

Claims (8)

An organic light-emitting compound represented by the following compound 49 or 51.

delete delete delete 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. The method according to claim 6,
Wherein the organic electroluminescent compound is contained as a phosphorescent green host material. 7. 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.