KR20100130068A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

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

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KR20100130068A
KR20100130068A KR1020090048729A KR20090048729A KR20100130068A KR 20100130068 A KR20100130068 A KR 20100130068A KR 1020090048729 A KR1020090048729 A KR 1020090048729A KR 20090048729 A KR20090048729 A KR 20090048729A KR 20100130068 A KR20100130068 A KR 20100130068A
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alkyl
light emitting
arylsilyl
tri
aryl
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KR1020090048729A
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윤승수
김성민
김봉옥
권혁주
음성진
조영준
김영길
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다우어드밴스드디스플레이머티리얼 유한회사
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Priority to KR1020090048729A priority Critical patent/KR20100130068A/en
Priority to JP2012513865A priority patent/JP2012528853A/en
Priority to PCT/KR2010/003457 priority patent/WO2010140802A1/en
Priority to CN2010800349455A priority patent/CN102575155A/en
Priority to TW099117723A priority patent/TW201105778A/en
Publication of KR20100130068A publication Critical patent/KR20100130068A/en

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Abstract

PURPOSE: An organic electroluminescent compound is provided to ensure good blue luminous efficiency, lifetime property of materials, and to prepare an organic electroluminescent diode with high efficiency and durability. CONSTITUTION: An organic electroluminescent compound is represented by chemical formula 1. In chemical formula 1, A is hydrogen or a functional group of chemical formula 1-a; Ar1 and Ar2 are independently chemical bond, (C6-C60) arylene or (C2-C60) heteroarylene; at least one of Z1-Z5 and at least one of Z11-Z15 is nitrogen atom and the rest of carbon atom.

Description

신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자{Novel organic electroluminescent compounds and organic electroluminescent device using the same}Novel organic electroluminescent compounds and organic electroluminescent device using the same

본 발명은 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자에 관한 것으로, 보다 구체적으로는 청색 발광 재료로서 사용되는 신규한 유기 발광 화합물 및 이를 도판트로서 채용하고 있는 유기 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic light emitting device including the same, and more particularly to a novel organic light emitting compound used as a blue light emitting material and an organic light emitting device employing the same as a dopant.

표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있으며, 1987년 이스트만 코닥(Eastman Kodak)사에서는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display element that has a wide viewing angle, excellent contrast, and high response speed.Eastman Kodak Co., Ltd. in 1987 An organic EL device using a low molecular aromatic diamine and an aluminum complex as a light emitting layer formation material was first developed [Appl. Phys. Lett. 51, 913, 1987].

유기 EL 소자에서 발광 효율, 수명 등의 성능을 결정하는 가장 중요한 요인은 발광 재료로서, 이러한 발광 재료에 요구되는 몇 가지 특성으로는 고체상태에서 형광 양자 수율이 커야하고, 전자와 정공의 이동도가 높아야 하며, 진공 증착시 쉽게 분해되지 않아야 하고, 균일한 박막을 형성, 안정해야한다. The most important factor that determines the performance of light emission efficiency, lifespan, etc. in the organic EL device is a light emitting material. Some characteristics required for such a light emitting material include a high fluorescence quantum yield in the solid state, and mobility of electrons and holes. It should be high, not easily decomposed during vacuum deposition, and should form and stabilize a uniform thin film.

유기 발광 재료는 크게 고분자 재료와 저분자 재료로 나눌 수 있는데, 저분자 계열의 재료는 분자 구조 면에서 금속 착화합물과 금속을 포함하지 않는 순수 유기 발광 재료가 있다. 이러한 발광 재료로는 트리스(8-퀴놀리놀라토)알루미늄 착제 등의 킬레이트 착제, 쿠마린 유도체, 테트라페닐부타디엔 유도체, 비스스타이릴아릴렌 유도체, 옥사다이아졸 유도체 등의 발광 재료가 알려져 있고, 이들로부터는 청색에서 적색까지의 가시 영역 발광을 얻을 수 있다고 보고되었고 컬러 표시 소자의 실현이 기대되고 있다.Organic light emitting materials can be classified into high molecular materials and low molecular materials. Low molecular materials include pure organic light emitting materials that do not contain metal complexes and metals in terms of molecular structure. As such light emitting materials, light emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives are known. It has been reported that visible light emission from blue to red can be obtained and the realization of color display elements is expected.

한편, 청색 재료의 경우, 이데미쓰-고산의 DPVBi(화합물 a) 이후로 많은 재료들이 개발되어 상업화되어 있으며, 이데미쓰-고산의 청색 재료 시스템과 코닥의 디나프틸안트라센(dinaphthylanthracen, 화합물 b), 테트라(t-부틸)페릴렌(tetra(t-butyl)perlyene, 화합물 c) 시스템 등이 알려져 있으나, 아직도 많은 연구 개발이 이루어져야 할 것으로 판단된다. 현재까지 가장 효율이 좋다고 알려진 이데미쓰-고산의 디스트릴(distryl)화합물의 시스템은 파워 효율의 경우, 6 lm/W이고, 소자 수명이 30,000 시간 이상으로 좋기는 하나, 구동 시간에 따른 색순도의 저하로 인하여 풀컬러 디스플레이에 적용했을 때, 수명이 불과 수천시간에 불과하다. 청색 발광은 발광 파장이 장파장 쪽으로 조금만 이동해도 발광 효율 측면에서는 유리해지나, 순청색을 만족시키지 못해 고품위의 디스플레이에는 적용이 쉽지 않은 문제점을 갖고 있으며, 색순도, 효율 및 열안정성에 문제가 있어 연구 개발이 시급한 부분이라고 하겠다.On the other hand, in the case of blue materials, many materials have been developed and commercialized since Idemitsu-Alpine DPVBi (Compound a), and the Idemitsu-Alpine Blue Material System and Kodak's dinaphthylanthracen (Compound b), Tetra (t-butyl) perlyene (compound c) system is known, but much research and development is still required. The system of Idemitsu-high acid disryl compound, which is known to be the most efficient so far, has a power efficiency of 6 lm / W and a device life of more than 30,000 hours, but the color purity decreases with driving time. When applied to a full-color display, its lifetime is only thousands of hours. Blue light emission is advantageous in terms of luminous efficiency even if the light emission wavelength is shifted toward the longer wavelength, but it is not easy to apply to high-quality display because it does not satisfy pure blue color, and there is a problem in color purity, efficiency and thermal stability, so that research and development It is an urgent part.

Figure 112009033388514-PAT00003
Figure 112009033388514-PAT00003

따라서, 본 발명자들은 상기의 종래의 문제점을 해결하기 위하여 노력한 결과, 발광 효율이 뛰어나고 수명이 획기적으로 개선된 유기 발광 소자를 실현하기 위한 새로운 발광 화합물을 발명하게 되었다.Accordingly, the present inventors have endeavored to solve the above-mentioned conventional problems. As a result, the inventors have invented a new light emitting compound for realizing an organic light emitting device having excellent light emission efficiency and a markedly improved lifetime.

본 발명의 목적은 상기한 문제점들을 해결하기 위하여 기존의 도판트 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며, 또 다른 목적으로서 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 발광 소자를 제공하는 것이다.Disclosure of Invention An object of the present invention is to provide an organic light emitting compound having an excellent luminescence efficiency and device life, and having an appropriate color coordinate, to solve the above problems, and having an appropriate color coordinate. It is to provide an organic light emitting device having high efficiency and long life, which is employed as a light emitting material.

본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 발광효율이 좋고 재료의 색순도 및 수명특성이 뛰어나 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by Formula 1 and an organic light emitting device including the same, the organic light emitting compound according to the present invention has excellent luminous efficiency and excellent color purity and life characteristics of the material OLED device having excellent driving life There is an advantage to manufacture.

[화학식 1][Formula 1]

Figure 112009033388514-PAT00004
Figure 112009033388514-PAT00004

[상기 화학식 1에서, A는 수소 또는

Figure 112009033388514-PAT00005
이며;[In Formula 1, A is hydrogen or
Figure 112009033388514-PAT00005
Is;

Ar1 및 Ar2는 서로 독립적으로 화학결합이거나 (C6-C60)아릴렌 또는 N, O 또는 S로부터 선택된 하나 이상의 헤테로 원자를 포함하는 (C2-C60)헤테로아릴렌이고, 상기 헤테로아릴렌의 탄소원자는 Se로 더 치환될 수 있으며;Ar 1 and Ar 2 are independently (C6-C60) arylene chemically bonded to each other or (C2-C60) heteroarylene containing at least one hetero atom selected from N, O or S, and a carbon source of the heteroarylene Can be further substituted with Se;

Z1 내지 Z5 중 적어도 하나 및 Z11 내지 Z15 중 적어도 하나는 질소 원자이고, 나머지는 탄소 원자이며, 상기 질소 원자의 경우에는 치환기가 존재하지 않고;At least one of Z 1 to Z 5 and at least one of Z 11 to Z 15 is a nitrogen atom, the remainder is a carbon atom, and in the case of the nitrogen atom there is no substituent;

R1 내지 R5 및 R11 내지 R15는 서로 독립적으로 수소, 중수소, (C1-C60)알킬, (C3-C60)사이클로알킬, (C6-C60)아릴, (C2-C60)헤테로아릴, (C1-C60)알콕시, (C6-C60)아릴옥시, 모노 또는 디(C1-C60)알킬아미노, 모노 또는 디(C6-C60)아릴아미노, (C6-C60)아르(C1-C60)알킬아미노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴이고, 상기 R1 내지 R5 또는 R11 내지 R15는 각각 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 O, S 또는 NR21로 더 치환될 수 있고, 상기 알케닐렌의 CH는 N으로 더 치환될 수 있고;R 1 to R 5 and R 11 to R 15 are each independently hydrogen, deuterium, (C1-C60) alkyl, (C3-C60) cycloalkyl, (C6-C60) aryl, (C2-C60) heteroaryl, ( C1-C60) alkoxy, (C6-C60) aryloxy, mono or di (C1-C60) alkylamino, mono or di (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkylamino, Tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl, wherein R 1 to R 5 or R 11 to R 15 are each adjacent substituents And (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form a fused ring, wherein the carbon atom of the alkylene is further substituted with O, S or NR 21 . And the CH of the alkenylene may be further substituted with N;

R21은 수소, 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 모폴리노, 티오모폴리노, 피페리디노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C3-C60)사이클로알킬, 아다만틸, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, (C1-C60)트리알킬실릴, 디(C1-C60)알 킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴이고;R 21 is one selected from hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, morpholino, thiomorpholino, piperidino, N, O and S 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, adamantyl, halogen, cyano, (C6-C60) aryl, (C2-C60) heteroaryl, (C1-C60) ) Trialkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl;

X 및 Y는 서로 독립적으로 화학결합이거나, -(CR31R32)n-, -N(R33)-, -Si(R34)(R35)-, -O-, -S-, -Se-, -P(R36)-, 또는 -(R37)C=C(R38)-이며, n은 1 내지 4의 정수이고;X and Y are each independently a chemical bond or-(CR 31 R 32 ) n- , -N (R 33 )-, -Si (R 34 ) (R 35 )-, -O-, -S-,- Se-, -P (R 36 )-, or-(R 37 ) C = C (R 38 )-, n is an integer from 1 to 4;

R31 내지 R38은 서로 독립적으로 수소, 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 모폴리노, 티오모폴리노, 피페리디노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C3-C60)사이클로알킬, 아다만틸, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴, 트리(C6-C60)아릴실릴이거나, R31과 R32, R34와 R35 또는 R37과 R38은 서로 독립적으로 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 스피로고리 또는 융합고리를 형성할 수 있고;R 31 to R 38 are independently of each other hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, morpholino, thiomorpholino, piperidino, N, 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, adamantyl, halogen, cyano, (C6-C60) aryl, (C2-C60) hetero, including one or more selected from O and S Aryl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, or R 31 and R 32 , R 34 and R 35 Or R 37 and R 38 may be independently linked to each other with (C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring to form a spirogory or fused ring;

Ar1 및 Ar2의 아릴렌 또는 헤테로아릴렌, R1 내지 R5, R11 내지 R15, R21 및 R31 내지 R38의 알킬, 사이클로알킬, 아릴, 헤테로아릴, 알콕시, 아릴옥시, 알킬아미노, 아릴아미노, 아르알킬아미노, 트리알킬실릴, 디알킬아릴실릴 또는 트리아릴실릴은 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로사이클로알킬, (C3-C60)사이클로알킬, 할로겐, 시아노, (C6-C60)아릴, (C2-C60) 헤테로아릴, (C6-C60)아르(C1-C60)알킬, (C1-C60)알킬(C6-C60)아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로부터 선택되는 하나 이상의 치환기가 더 치환될 수 있다.]Arylene or heteroarylene of Ar 1 and Ar 2 , R 1 to R 5 , R 11 to R 15 , R 21 and R 31 to R 38 alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkyl Amino, arylamino, aralkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl are deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, piperidino, 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, halogen, cyano, (C6-C60) aryl containing one or more selected from morpholino, thiomorpholino, N, O and S , (C2-C60) heteroaryl, (C6-C60) ar (C1-C60) alkyl, (C1-C60) alkyl (C6-C60) aryl, tri (C1-C60) alkylsilyl, di (C1-C60) One or more substituents selected from alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted.]

본 발명에 기재되어 있는 “(C1-C60)알킬”부분이 포함되어 있는 치환체들은 1 내지 60개의 탄소수를 가질 수도 있고, 1 내지 20개의 탄소수를 가질 수도 있고, 1 내지 10개의 탄소수를 가질 수도 있다. “(C6-C60)아릴”부분이 포함되어 있는 치환체들은 6 내지 60개의 탄소수를 가질 수도 있고, 6 내지 20개의 탄소수를 가질 수도 있고, 6 내지 12개의 탄소수를 가질 수도 있다. “(C3-C60)헤테로아릴”부분이 포함되어 있는 치환체들은 3 내지 60개의 탄소수를 가질 수도 있고, 4 내지 20개의 탄소수를 가질 수도 있고, 4 내지 12개의 탄소수를 가질 수도 있다. “(C3-C60)시클로알킬”부분이 포함되어 있는 치환체들은 3 내지 60개의 탄소수를 가질 수도 있고, 3 내지 20개의 탄소수를 가질 수도 있고, 3 내지 7개의 탄소수를 가질 수도 있다. “(C2-C60)알케닐 또는 알키닐”부분이 포함되어 있는 치환체들은 2 내지 60개의 탄소수를 가질 수도 있고, 2 내지 20개의 탄소수를 가질 수도 있고, 2 내지 10개의 탄소수를 가질 수도 있다. Substituents containing the "(C1-C60) alkyl" moiety described in the present invention may have 1 to 60 carbon atoms, 1 to 20 carbon atoms, or 1 to 10 carbon atoms. . Substituents containing the "(C6-C60) aryl" moiety may have 6 to 60 carbon atoms, 6 to 20 carbon atoms, or 6 to 12 carbon atoms. Substituents containing the "(C3-C60) heteroaryl" moiety may have 3 to 60 carbon atoms, 4 to 20 carbon atoms, or 4 to 12 carbon atoms. Substituents containing the "(C3-C60) cycloalkyl" moiety may have 3 to 60 carbon atoms, may have 3 to 20 carbon atoms, or may have 3 to 7 carbon atoms. Substituents containing the "(C2-C60) alkenyl or alkynyl" moiety may have 2 to 60 carbon atoms, may have 2 to 20 carbon atoms, or may have 2 to 10 carbon atoms.

본 발명에 기재된 「알킬」은 탄소 원자 및 수소 원자만으로 구성된 직쇄 또는 분지쇄의 포화된 1가 탄화수소 라디칼 또는 그의 조합물을 포함하며, 또한, 「알콕시」는 -O-알킬기로, 여기서 알킬은 상기 정의한 바와 같다."Alkyl" as described herein includes straight or branched chain saturated monovalent hydrocarbon radicals or combinations thereof consisting solely of carbon atoms and hydrogen atoms, wherein "alkoxy" is an -O-alkyl group, wherein alkyl is As defined.

본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함한다. 또한, 하나이상의 아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트라이페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다."Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and is a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes the system. Also included are structures in which one or more aryls are bonded via a chemical bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like. It is not limited to this.

본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 N, O 및 S로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠 환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 하나 이상의 헤테로아릴이 화학결합을 통하여 결합되어 있는 구조도 포함된다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로 퓨릴, 티에닐, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아지닐, 테트라지닐, 트리아졸릴, 테트라졸릴, 퓨라자닐, 피리딜, 피라지닐, 피리미디닐, 피리다지닐 등의 단환 헤테로아릴, 벤조퓨릴, 벤조티에닐, 이소벤조퓨릴, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴놀리진일, 퀴녹 살리닐, 카바졸릴, 페난트리디닐, 벤조디옥솔릴 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다."Heteroaryl" described in the present invention means an aryl group containing 1 to 4 heteroatoms selected from N, O and S as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon, and 5 to 6 members Monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. Also included are structures in which one or more heteroaryls are bonded via chemical bonds. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl Monocyclic heteroaryl such as furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoy Soxazolyl, Benzoxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cinolinyl, Quinazolinyl, Quinolinzyl, Quinoxalinyl, Carbazolyl, Phenantri Polycyclic heteroaryls such as diyl, benzodioxolyl and the like and their corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like. Do not.

본 발명에 기재된 「스피로고리」은 2개의 고리가 오로지 1개의 원자(sp³ 혼성탄소)를 공유하고 있는 탄화수소기로, 두 개의 고리에 공유되어 있는 원자를 스파이로 원자(나선모양을 의미하는 그리스어 spiro에 유래한다)라고 하며 탄소 규소의 예가 알려져 있다. The "spirocyclic ring" described in the present invention is a hydrocarbon in which two rings share only one atom (sp³ hybrid carbon), and the atom shared in two rings is used as a spiro atom (spiral Greek spiro). It is derived from, and examples of carbon silicon are known.

또한, 본 발명의 유기 발광 화합물은 하기 화학식 2 또는 3으로 표시되는 화합물을 포함한다.In addition, the organic light emitting compound of the present invention includes a compound represented by the following formula (2) or (3).

[화학식 2][Formula 2]

Figure 112009033388514-PAT00006
Figure 112009033388514-PAT00006

[화학식 3](3)

Figure 112009033388514-PAT00007
Figure 112009033388514-PAT00007

[상기 화학식 2 및 3에서, X, Y, Ar1, Ar2, Z1 내지 Z5, Z11 내지 Z15, R1 내지 R15 및 R11 내지 R15는 상기 화학식 1에서의 정의와 동일하다.][In Formulas 2 and 3, X, Y, Ar 1 , Ar 2 , Z 1 to Z 5 , Z 11 to Z 15 , R 1 to R 15 and R 11 to R 15 are the same as defined in Formula 1 Do.]

상기 R1 내지 R5 및 R11 내지 R15는 서로 독립적으로 수소, 중수소, CD3, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 벤질, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 메톡시, 에톡시, n-프로폭시, i-프로폭시, n-부톡시, i-부톡시, t-부톡시, n-펜톡시, i-펜톡시, n-헥실옥시, n-헵톡시, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 시클로헵틸, 시클로옥틸, 시클로노닐, 시클로데실, C6D5, 페닐, 툴릴, 부틸페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, 페녹시, 디메틸아미노, 모노메틸아미노, 벤질아미노, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸디메틸실릴, 디메틸페닐실릴 또는 트리페닐실릴이거나, R1 내지 R5 또는 R11 내지 R15는 각각 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알케닐렌의 CH는 N으로 더 치환될 수 있다.R 1 to R 5 and R 11 to R 15 are each independently hydrogen, deuterium, CD 3 , methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl , i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, benzyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluor Propyl, perfluorobutyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hex Siloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, C 6 D 5 , phenyl, turyl, butylphenyl, naphthyl, biphenyl, Fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimida Sleepy, pyrazineyl, Pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, benzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, Phenoxy, dimethylamino, monomethylamino, benzylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethylphenylsilyl or triphenylsilyl, or R 1 to R 5 or R 11 to R 15 may be linked to (C3-C60) alkylene or (C3-C60) alkenylene with or without adjacent substituents and fused ring, respectively, to form a fused ring, and the alkenylene CH may be further substituted with N.

또한 상기

Figure 112009033388514-PAT00008
및
Figure 112009033388514-PAT00009
는 서로 독립적으로 하기 구조에서 선택되어지나, 이에 한정되는 것은 아니다.Also above
Figure 112009033388514-PAT00008
And
Figure 112009033388514-PAT00009
Are independently selected from the following structures, but are not limited thereto.

Figure 112009033388514-PAT00010
Figure 112009033388514-PAT00010

상기

Figure 112009033388514-PAT00011
는 하기 구조에서 선택되어지나, 이에 한정되는 것은 아니다.remind
Figure 112009033388514-PAT00011
Is selected from the following structure, but is not limited thereto.

Figure 112009033388514-PAT00012
Figure 112009033388514-PAT00012

[R31 내지 R38은 서로 독립적으로 수소, 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 모폴리노, 티오모폴리노, 피페리디노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C3-C60)사이클로알킬, 아다만틸, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴, 트리(C6-C60)아릴실릴고; 상기 R21 내지 R28의 알킬, 사이클로알킬, 아릴, 헤테로아릴, 알콕시, 트리알킬실릴, 디알킬아릴실릴 또는 트리아릴실릴은 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로사이클로알킬, (C3-C60)사이클로알킬, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, (C6-C60)아르(C1-C60)알킬, (C1-C60)알킬(C6-C60)아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로부터 선택되는 하나 이상의 치환기가 더 치환될 수 있다.][R 31 to R 38 are independently of each other hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, morpholino, thiomorpholino, piperidino, N 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, adamantyl, halogen, cyano, (C6-C60) aryl, (C2-C60) containing at least one selected from Heteroaryl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl; Alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 21 to R 28 may be deuterium, (C 1 -C 60) alkyl, halo (C 1 -C 60) alkyl, ( C6-C60) 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, halogen, including one or more selected from alkoxy, piperidino, morpholino, thiomorpholino, N, O and S , Cyano, (C6-C60) aryl, (C2-C60) heteroaryl, (C6-C60) ar (C1-C60) alkyl, (C1-C60) alkyl (C6-C60) aryl, tri (C1-C60 One or more substituents selected from alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted.]

또한, 상기 Ar1 및 Ar2는 서로 독립적으로 화학결합이거나, 하기 구조에서 선택되는 아릴렌 또는 헤테로아릴렌이나, 이에 한정되는 것은 아니다.In addition, Ar 1 and Ar 2 may be independently a chemical bond or arylene or heteroarylene selected from the following structures, but is not limited thereto.

Figure 112009033388514-PAT00013
Figure 112009033388514-PAT00013

Figure 112009033388514-PAT00014
Figure 112009033388514-PAT00014

[R41은 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로사이클로알킬, (C3-C60)사이클로알킬, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, (C6-C60)아르(C1-C60)알킬, (C1-C60)알킬(C6-C60)아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴이고, m은 0 내지 4의 정수이다.][R 41 is one or more selected from deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, piperidino, morpholino, thiomorpholino, N, O and S 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, halogen, cyano, (C6-C60) aryl, (C2-C60) heteroaryl, (C6-C60) ar (C1-) C60) alkyl, (C1-C60) alkyl (C6-C60) aryl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl , m is an integer of 0 to 4.]

더욱 구체적으로, 상기 Ar1 및 Ar2는 서로 독립적으로 화학결합이거나, 하기 구조에서 선택되는 아릴렌 또는 헤테로아릴렌이나, 이에 한정되지는 않는다.More specifically, Ar 1 and Ar 2 are each independently a chemical bond or arylene or heteroarylene selected from the following structures, but is not limited thereto.

Figure 112009033388514-PAT00015
Figure 112009033388514-PAT00015

본 발명에 따른 유기 발광 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있으나, 하기 화합물이 본 발명을 한정하는 것은 아니다.The organic light emitting compound according to the present invention may be more specifically exemplified as the following compound, but the following compound does not limit the present invention.

Figure 112009033388514-PAT00016
Figure 112009033388514-PAT00016

Figure 112009033388514-PAT00017
Figure 112009033388514-PAT00017

Figure 112009033388514-PAT00018
Figure 112009033388514-PAT00018

Figure 112009033388514-PAT00019
Figure 112009033388514-PAT00019

Figure 112009033388514-PAT00020
Figure 112009033388514-PAT00020

Figure 112009033388514-PAT00021
Figure 112009033388514-PAT00021

발명에 따른 유기 발광 화합물은 예를 들어 하기 반응식 1에 나타난 바와 같이, 제조될 수 있으며, 하기 반응식으로만 한정되는 것은 아니다.The organic light emitting compound according to the invention can be prepared, for example, as shown in Scheme 1 below, but is not limited to the following scheme.

[반응식 1]Scheme 1

Figure 112009033388514-PAT00022
Figure 112009033388514-PAT00022

[상기 반응식에서, X, Y, Ar1, Ar2, Z1 내지 Z5, Z11 내지 Z15, R1 내지 R15 및 R11 내지 R15는 각각 상기 화학식 1에서 정의한 바와 같다.][In the above scheme, X, Y, Ar 1 , Ar 2 , Z 1 to Z 5 , Z 11 to Z 15 , R 1 to R 15 and R 11 to R 15 are the same as defined in Formula 1, respectively.]

또한 본 발명은 유기 발광 소자를 제공하며, 본 발명에 따른 유기 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. In another aspect, the present invention provides an organic light emitting device, the organic light emitting device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound of Chemical Formula 1.

본 발명에 따른 유기 발광 소자는 상기 유기물층이 발광층을 포함하며, 상기 발광층은 상기 화학식 1의 하나 이상의 유기 발광 화합물을 발광 도판트로 하여 하나 이상의 호스트를 포함하는 것을 특징으로 하며, 본 발명의 유기 발광 소자에 적 용되는 호스트는 특별히 제한되지 않으나, 하기 화학식 4 또는 화학식 5로 표시되는 화합물에서 선택되는 것이 바람직하다. 하기 화학식 3 또는 화학식 4의 호스트 화합물의 구체적인 구조는 특허출원 제10-2008-0060393호의 식별번호<162> 내지 <210>에 예시되어 있으며, 이에 한정되는 것은 아니다.The organic light emitting device according to the present invention is characterized in that the organic material layer includes a light emitting layer, and the light emitting layer includes at least one host using at least one organic light emitting compound of Formula 1 as a light emitting dopant, and the organic light emitting device of the present invention. The host to be applied to is not particularly limited, but is preferably selected from compounds represented by the following general formula (4) or (5). Specific structures of the host compounds represented by the following Chemical Formula 3 or Chemical Formula 4 are illustrated in the identification numbers <162> to <210> of Patent Application No. 10-2008-0060393, but are not limited thereto.

[화학식 4][Formula 4]

(Ar11)c-L1-(Ar12)d (Ar 11 ) c -L 1- (Ar 12 ) d

[화학식 5][Chemical Formula 5]

(Ar13)e-L2-(Ar14)f (Ar 13 ) e -L 2- (Ar 14 ) f

[상기 화학식 4 및 화학식 5에서,[In Formula 4 and Formula 5,

L1는 (C6-C60)아릴렌 또는 (C4-C60)헤테로아릴렌이고;L 1 is (C6-C60) arylene or (C4-C60) heteroarylene;

L2는 안트라세닐렌이며;L 2 is anthracenylene;

Ar11 내지 Ar14은 서로 독립적으로 수소이거나, 중수소, (C1-C60)알킬, (C1-C60)알콕시, 할로겐, (C4-C60)헤테로아릴, (C5-C60)시클로알킬 또는 (C6-C60)아릴로부터 선택되고, 상기 Ar11 내지 Ar14의 시클로알킬, 아릴 또는 헤테로아릴은 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, (C3-C60)시클로알킬, 할로겐, 시아노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로 이루어진 군으로부터 선택된 하나 이상이 치환되거나 치환되지 않은 (C6-C60)아릴 또는 (C4-C60)헤테로아릴, 할로겐이 치환되거나 치환되지 않 은 (C1-C60)알킬, (C1-C60)알콕시, (C3-C60)시클로알킬, 할로겐, 시아노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로 이루어지는 군에서 선택되는 하나 이상의 치환기가 더 치환될 수 있고;Ar 11 to Ar 14 are each independently hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60 Aryl and cycloalkyl, aryl or heteroaryl of Ar 11 to Ar 14 are deuterium, (C 1 -C 60) alkyl, halo (C 1 -C 60) alkyl, (C 1 -C 60) alkoxy, (C 3 -C 60) One or more selected from the group consisting of cycloalkyl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl or Unsubstituted (C6-C60) aryl or (C4-C60) heteroaryl, substituted or unsubstituted (C1-C60) alkyl, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, One or more substituents selected from the group consisting of cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted ;

c, d, e 및 f는 서로 독립적으로 0 내지 4의 정수이다.]c, d, e and f are each independently an integer from 0 to 4.]

상기 발광층의 의미는 발광이 이루어지는 층으로서 단일 층일 수 있으며, 또한 2개 이상의 층이 적층된 복수의 층일 수 있다. 본 발명의 구성에서의 호스트-도판트를 혼합하여 사용하는 경우, 본 발명의 발광 호스트에 의한 발광 효율의 현저한 개선을 확인할 수 있었다. 이는 0.5 내지 10중량%의 도핑 농도로 구성할 수 있는데, 기존의 다른 호스트 재료에 비하여 정공, 전자에 대한 전도성이 매우 뛰어나며, 물질 안정성을 매우 우수하여 발광효율 뿐만 아니라, 수명도 현저히 개선시키는 특성을 보여 주고 있다. 따라서, 상기 화학식 3 또는 화학식 4로부터 선택되는 화합물을 발광 호스트로 채택하는 경우, 본 발명의 화학식 1의 유기 발광 화합물의 전기적 단점을 상당히 보완해 주는 역할을 하고 있다고 설명할 수 있다.The light emitting layer may be a single layer as a light emitting layer, or may be a plurality of layers in which two or more layers are stacked. In the case of using a mixture of the host and dopants in the configuration of the present invention, a significant improvement in the luminous efficiency by the light emitting host of the present invention was confirmed. It can be composed of a doping concentration of 0.5 to 10% by weight, and has excellent conductivity for holes and electrons compared to other host materials, and has excellent material stability, which significantly improves luminous efficiency and lifetime. Is showing. Therefore, when the compound selected from Chemical Formula 3 or Chemical Formula 4 is adopted as the light emitting host, it can be explained that the organic light emitting compound of Chemical Formula 1 of the present invention significantly compensates for the electrical shortcomings.

본 발명의 유기 발광 소자에 있어서, 화학식 1의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있으며, 아릴아민계 화합물 또는 스티릴아릴아민계 화합물의 구체적인 예는 특허출원 제10-2008-0060393호의 식별번호<212> 내지 <224>에 예시되어 있으며, 이에 한정되는 것은 아니다.In the organic light emitting device of the present invention, an organic light emitting compound of Formula 1, and at the same time may include one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds, arylamine-based compounds or Specific examples of the styrylarylamine compound are exemplified in the identification numbers <212> to <224> of Patent Application No. 10-2008-0060393, but are not limited thereto.

또한, 본 발명의 유기 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 발광 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속을 더 포함할 수도 있고, 상기 유기물층은 발광층 및 전하생성층을 포함할 수 있다.In addition, in the organic light emitting device of the present invention, in the organic layer, in addition to the organic light emitting compound of Formula 1, from the group consisting of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element The organic material layer may further include one or more selected metals, and the organic material layer may include a light emitting layer and a charge generating layer.

본 발명의 화학식 1의 유기 발광 화합물을 포함하는 유기 발광 소자를 서브픽셀로 하고, Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au 및 Ag로 이루어진 군에서 선택되는 하나 이상의 금속화합물을 포함하는 서브픽셀 하나 이상을 동시에 병렬로 패터닝한 독립발광방식의 픽셀구조를 가진 유기 발광 소자를 구현할 수도 있다.An organic light emitting device including the organic light emitting compound of Formula 1 of the present invention is a subpixel, and includes Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag. An organic light emitting device having an independent light emitting pixel structure in which at least one subpixel including at least one metal compound selected from the group consisting of at least one metal is simultaneously patterned in parallel may be implemented.

또한, 상기 유기물층에 상기 유기 발광 화합물 이외에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있으며, 상기 청색, 녹색 또는 적색 발광을 하는 화합물은 출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In addition, the organic material layer may simultaneously include one or more organic light emitting layers emitting blue, red, or green light in addition to the organic light emitting compound to form an organic light emitting device that emits white light, and the blue, green, or red light emitting compound Is illustrated in, but not limited to, application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428.

본 발명의 유기 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 "표면층"이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해, 구동의 안 정화를 얻을 수 있다. 상기 칼코제나이드로서는 예컨대 SiOx(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON 등을 바람직하게 들 수 있으며, 할로겐화 금속으로서는 예컨대 LiF, MgF2, CaF2, 불화 희토류 금속 등을 바람직하게 들 수 있으며, 금속 산화물로서는 예컨대 Cs2O, Li2O, MgO, SrO, BaO, CaO 등을 바람직하게 들 수 있다.In the organic light emitting device of the present invention, at least one inner surface of the pair of electrodes includes at least one layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer (hereinafter, these are referred to as "surface layers"). It is preferable to arrange. Specifically, it is preferable to dispose a chalcogenide (containing oxide) layer of a metal of silicon and aluminum on the anode surface of the light emitting medium layer side and a metal halide or metal oxide layer on the cathode surface of the light emitting medium layer side. Do. In this way, driving stability can be obtained. Examples of the chalcogenide include SiO x (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON, SiAlON, and the like, and examples of the metal halide include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like are preferable. Examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.

또한, 본 발명의 유기 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식으로, 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있다. 바람직한 환원성 도판트로서는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다.Further, in the organic light emitting device of the present invention, it is also preferable to arrange a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transfer compound and the oxidative dopant on at least one surface of the pair of electrodes thus produced. Do. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region into the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.

본 발명에 따른 유기 발광화합물은 청색의 발광효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 양호한 OLED 소자를 제조할 수 있는 장점이 있다.The organic light emitting compound according to the present invention has an advantage of producing an OLED device having a good luminous efficiency of blue and excellent life characteristics of the material and having a very good driving life of the device.

이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명하나, 이는 단지 그 실시 양태를 예시하기 위한 것일 뿐, 본 발명의 범위를 한정하는 것은 아니다.Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same and a light emitting property of the device are described for the detailed understanding of the present invention, but the present invention is only intended to illustrate the embodiments of the present invention. It does not limit the scope of the invention.

[[ 제조예Production Example 1]화합물 2의 제조 1] Preparation of Compound 2

Figure 112009033388514-PAT00023
Figure 112009033388514-PAT00023

화합물 compound A A 의 제조Manufacture

100ml 둥근 바닥 플라스크 에 9,9-다이에틸-9H-플루오렌 7g(32.11mmol) 과 파라포름알데하이드 9.4g (32.11mmol) 을 넣고 진공건조 시킨 후 질소가스를 주입한다. 상기 플라스크에 30% HBr 50ml 을 첨가한 뒤 60 ℃로 가열하여 24시간 교반 시킨다. 반응이 끝나면 CHCl3로 추출한 뒤 NaHCO3로 3번 씻어준다. 상기 반응물은 브린(brine)으로 3회 세척하여 화합물 A 13g (31.8mmol, 99%) 을 얻었다.Into a 100 ml round bottom flask, 7 g (32.11 mmol) of 9,9-diethyl-9H-fluorene and 9.4 g (32.11 mmol) of paraformaldehyde were dried in vacuo, followed by nitrogen gas. 50 ml of 30% HBr was added to the flask, followed by heating to 60 ° C. and stirring for 24 hours. After the reaction, the mixture was extracted with CHCl 3 and washed three times with NaHCO 3 . The reaction was washed three times with brine to give 13 g of Compound A (31.8 mmol, 99%).

화합물 compound BB 의 제조Manufacture

50ml 둥근 바닥 플라스크에 화합물 A 5.00g (12.24mmol) 을 넣고 진공 건조시킨 후 질소가스를 주입한다. 트리에틸포스파이트(Triethylphospite) 8.1ml (48.96mmol) 을 넣고 185℃에서 6시간동안 환류교반한다. 반응이 종결되면 진공증류장치로 남아있는 트리에틸포스파이트를 제거하고 증류수로 세척하고에틸아세테이트로 추출한다. 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 에틸아세테이트를 전개 용매로 하여 컬럼크로마토그래피로 정제하여 화합물 B 4.9g(9,37mmol, 76%)를 얻었다. 5.00g (12.24mmol) of Compound A was placed in a 50 ml round bottom flask, and dried in vacuo, followed by nitrogen gas. Add 8.1ml (48.96mmol) of triethylphospite and stir at reflux for 6 hours at 185 ℃. After the reaction is completed, the remaining triethyl phosphite is removed by vacuum distillation apparatus, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator, and then purified by column chromatography using ethyl acetate as a developing solvent, to obtain Compound B 4.9 g (9,37 mmol, 76%).

화합물 compound CC 의 제조Manufacture

1000ml 둥근 바닥 플라스크에 2-브로모퀴놀린 (5g, 24mmol), 4-포밀페닐보로산 (3.59g, 24mmol) 및 테트라키스(트리페닐포스핀)팔라듐 (1.11g, 0.96mmol)을 넣고 톨루엔 168ml로 용해시킨다. 상기 플라스크에 2.0M 탄산나트륨 수용액 84ml(168.2mmol)와 에탄올 84ml를 첨가하고 120℃에서 2시간 동안 환류교반시킨다. 반응이 종결되면 에틸아세테이트로 추출하고 컬럼크로마토그래피로 정제하여 화합물 C 5g (21.4mmol, 89%) 을 얻었다.Into a 1000 ml round bottom flask, 2-bromoquinoline (5 g, 24 mmol), 4-formylphenylborolic acid (3.59 g, 24 mmol) and tetrakis (triphenylphosphine) palladium (1.11 g, 0.96 mmol) were added to 168 ml of toluene. To dissolve. 84 ml (168.2 mmol) of 2.0 M aqueous sodium carbonate and 84 ml of ethanol were added to the flask and stirred under reflux at 120 ° C. for 2 hours. When the reaction was terminated, extracted with ethyl acetate and purified by column chromatography to give a compound C 5g (21.4mmol, 89%).

화합물 compound 22 의 제조Manufacture

250ml 둥근바닥 플라스크에 화합물 B (5g, 9.56mmol)와 화합물 C (4.46g , 19.13mmol)를 넣고 진공 건조시킨 뒤 질소가스를 채운다. THF 50ml를 첨가한 후 0℃에서 포타슘 tert-부톡사이드 (1.0M in THF) 19ml(19.13 mmol)를 천천히 첨가하고 10분간 교반한다. 온도를 실온으로 올린 뒤 1시간동안 교반한다. 반응이 종결되 면 과량의 증류수를 넣고 형성되는 침전물을 거른다. 걸러진 고체를 에탄올로 세척하여 정제하여 화합물 2 3.25g (4.78mmol, 50%)을 얻었다. Compound B (5g, 9.56mmol) and Compound C (4.46g, 19.13mmol) were put in a 250ml round bottom flask and dried in vacuo and filled with nitrogen gas. After adding 50 ml of THF, 19 ml (19.13 mmol) of potassium tert-butoxide (1.0M in THF) was added slowly at 0 ° C. and stirred for 10 minutes. Raise the temperature to room temperature and stir for 1 hour. At the end of the reaction, excess distilled water is added and the precipitate formed is filtered off. The filtered solid was washed with ethanol and purified to give 3.25 g (4.78 mmol, 50%) of compound 2 .

1H NMR(CDCl3, 200MHz) δ = 0.9(6H, m), 1.91(4H, m), 6.95(4H, m), 7.35(2H, m), 7.54~7.6(8H, m), 7.71(2H, m), 7.78(2H, m), 7.87(2H, m), 7.98(2H, m), 8.06~8.1(4H, m), 8.3(4H, m) 1 H NMR (CDCl 3 , 200 MHz) δ = 0.9 (6H, m), 1.91 (4H, m), 6.95 (4H, m), 7.35 (2H, m), 7.54-7.6 (8H, m), 7.71 ( 2H, m), 7.78 (2H, m), 7.87 (2H, m), 7.98 (2H, m), 8.06-8.1 (4H, m), 8.3 (4H, m)

[[ 제조예Production Example 2] 화합물 63의 제조 2] Preparation of Compound 63

Figure 112009033388514-PAT00024
Figure 112009033388514-PAT00024

화합물 compound 6363 의 제조Manufacture

250ml 둥근바닥 플라스크에 화합물 B (5g, 9.56mmol)와 퀴놀린-2-카브알데하이드(quinoline-2-carbaldehyde) (3g, 19.13mmol)을 넣고 진공 건조시킨 뒤 질소가스를 채운다. THF 50ml를 첨가한 후 0℃에서 포타슘 tert-부톡사이드 (1.0M in THF) 19ml(19.13mmol)를 천천히 첨가하고 10분간 교반한다. 온도를 실온으로 올린 뒤 1시간동안 교반한다. 반응이 끝나면 과량의 증류수를 넣고 형성되는 침전물을 거른다. 걸러진 고체를 에탄올로 씻어 정제하여 화합물 63 4.5g (8.51mmol, 90%)을 얻었다. Compound B (5g, 9.56mmol) and quinoline-2-carbaldehyde (3g, 19.13mmol) were added to a 250ml round bottom flask, and vacuum dried and filled with nitrogen gas. After adding 50 ml of THF, 19 ml (19.13 mmol) of potassium tert-butoxide (1.0 M in THF) was added slowly at 0 ° C. and stirred for 10 minutes. Raise the temperature to room temperature and stir for 1 hour. After the reaction, excess distilled water is added and the precipitate formed is filtered off. The filtered solid was washed with ethanol and purified to give 4.5 g (8.51 mmol, 90%) of compound 63 .

1H NMR(CDCl3, 200MHz) δ = 0.9(6H, m), 1.91(4H, m), 7.2(2H, m), 7.37~7.42(4H, m), 7.56~7.6(6H, m), 7.78~7.82(4H, m), 7.98(2H, m), 8.06(2H, m), 8.24(2H, m) 1 H NMR (CDCl 3 , 200 MHz) δ = 0.9 (6H, m), 1.91 (4H, m), 7.2 (2H, m), 7.37-7.42 (4H, m), 7.56-7.6 (6H, m), 7.78-7.82 (4H, m), 7.98 (2H, m), 8.06 (2H, m), 8.24 (2H, m)

[[ 제조예Production Example 3]화합물 64의 제조 3] Preparation of Compound 64

Figure 112009033388514-PAT00025
Figure 112009033388514-PAT00025

화합물 compound F F 의 제조Manufacture

250ml 플라스크에 부틸마그네슘클로라이드 (730mg, 6.3mmol)를 넣고 THF 40ml로 녹인 후 -10℃로 냉각시킨다. n-부틸리튬 5.1ml을 첨가한 후 1시간 동안 -10도를 유지하며 교반시킨다. 3-브로모퀴놀린 (3.5g, 17mmol)을 THF 20ml에 녹여 -30℃에서 상기 플라스크에 첨가한 후, -10℃로 온도를 올려 2시간 동안 교반시킨다. THF 30ml에 2,5-다이브로모피리딘 (4g, 17mmol)을 녹여, Pd(dba)2 (480mg, 830μmol)와 dppf (470mg, 830μmol)를 함께 첨가한다. 1시간 동안 -10℃에서 교반시킨 후 실온으로 올려 18시간 동안 교반시킨 후 포화 NH4Cl 수용액을 첨가하여 반 응을 종결시킨다. 에틸아세테이트로 추출한 후 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 F 2.5g (8.76mmol, 53%)를 얻었다. Butyl magnesium chloride (730mg, 6.3mmol) was added to a 250ml flask and dissolved in 40ml of THF, followed by cooling to -10 ℃. After addition of 5.1 ml of n-butyllithium, the mixture is stirred for 1 hour while maintaining at -10 degrees. 3-bromoquinoline (3.5 g, 17 mmol) is dissolved in 20 ml of THF, added to the flask at -30 ° C, and the temperature is raised to -10 ° C and stirred for 2 hours. Dissolve 2,5-dibromopyridine (4 g, 17 mmol) in 30 ml of THF and add Pd (dba) 2 (480 mg, 830 μmol) and dppf (470 mg, 830 μmol) together. After stirring for 1 hour at −10 ° C., the temperature was raised to room temperature, stirred for 18 hours, and the reaction was terminated by addition of a saturated NH 4 Cl aqueous solution. After extracting with ethyl acetate, the organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and then purified by column chromatography to obtain Compound F 2.5g (8.76mmol, 53%).

화합물 compound GG 의 제조Manufacture

100 ml 둥근바닥 플라스크에 화합물 F 2.5g (10.7mmol)을 넣고 진공 건조 시킨 뒤 아르곤 가스를 채운다. THF 25ml를 첨가한 후 -78℃로 냉각시킨다. n-뷰틸리튬 (5ml, 12.84mmol)을 천천히 첨가한 뒤 1시간 동안 저온을 유지하며 교반한다. -78℃에서 DMF 1ml (12.84mmol)을 첨가한 뒤 1시간 교반한다. 반응이 끝나면 0℃에서 1M HCl을 첨가한 뒤 증류수로 씻어주고 에틸아세테이트로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 G 1.68g (7.17mmol, 82%)를 얻었다. Add 2.5 g (10.7 mmol) of Compound F to a 100 ml round bottom flask, vacuum dry and fill with argon gas. 25 ml of THF is added and then cooled to -78 ° C. Slowly add n-butyllithium (5ml, 12.84mmol) and stir at low temperature for 1 hour. After adding 1 ml (12.84 mmol) of DMF at -78 ° C, the mixture is stirred for 1 hour. After the reaction, 1M HCl was added at 0 ° C, washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography to obtain Compound G 1.68g (7.17mmol, 82%).

화합물 compound 6464 의 제조Manufacture

250ml 둥근바닥 플라스크에 화합물 G (1.68g, 7.17mmol)와 화합물 B (1.7g, 3.25mmol)을 넣고 진공 건조시킨 뒤 질소가스를 채운다. THF 20ml를 첨가한 후 0℃에서 포타슘 tert-부톡사이드 (1.0M in THF) 3.25ml(3.25mmol)를 천천히 첨가하고 10분간 교반한다. 온도를 실온으로 올린 뒤 1시간동안 교반한다. 반응이 끝나면 에틸아세테이트로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 64 1.55g (2.26mmol, 70%)를 얻었다. Compound G (1.68g, 7.17mmol) and Compound B (1.7g, 3.25mmol) were put into a 250ml round bottom flask and dried in vacuo and filled with nitrogen gas. After adding 20 ml of THF, 3.25 ml (3.25 mmol) of potassium tert-butoxide (1.0 M in THF) was added slowly at 0 ° C. and stirred for 10 minutes. Raise the temperature to room temperature and stir for 1 hour. After the reaction, ethyl After removal of the solvent after the organic layer was extracted with acetate on a rotary evaporator after drying over MgSO 4 was purified by column chromatography to obtain the compound 64 1.55g (2.26mmol, 70%) .

1H NMR(CDCl3, 200MHz) δ = 0.9(6H, m), 1.91(4H, m), 6.95(4H, m), 7.42(2H, m), 7.59~7.6(4H, m), 7.68(2H, m), 7.78~7.82(4H, m), 7.98(2H, m), 8.06(2H, m), 8.29~8.36(6H, m), 8.93(2H, m) 1 H NMR (CDCl 3 , 200 MHz) δ = 0.9 (6H, m), 1.91 (4H, m), 6.95 (4H, m), 7.42 (2H, m), 7.59-7.6 (4H, m), 7.68 ( 2H, m), 7.78-7.82 (4H, m), 7.98 (2H, m), 8.06 (2H, m), 8.29-8.36 (6H, m), 8.93 (2H, m)

[[ 제조예Production Example 4] 화합물 65의 제조 4] Preparation of Compound 65

Figure 112009033388514-PAT00026
Figure 112009033388514-PAT00026

화합물 compound HH 의 제조Manufacture

500 ml 둥근바닥 플라스크에 2-브로모-9,9-디에틸-9H-플루오렌 10g (33.19mmol)을 넣고 진공 건조 시킨 뒤 아르곤 가스를 채운다. THF 250ml를 첨가한 후 -78℃로 냉각시킨다. n-뷰틸리튬 (19.9ml, 49.79mmol)을 천천히 첨가한 뒤 1시간 동안 저온을 유지하며 교반한다. -78℃에서 DMF 3.8ml (49.79mmol)을 첨가한 뒤 1시간 교반한다. 반응이 끝나면 0℃에서 1M HCl을 첨가한 뒤 증류수로 씻어주고 EA 로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 H 6g (72%)를 얻었다. 10 g (33.19 mmol) of 2-bromo-9,9-diethyl-9H-fluorene was added to a 500 ml round bottom flask, followed by vacuum drying and filling with argon gas. 250 ml of THF is added and then cooled to -78 ° C. Slowly add n-butyllithium (19.9ml, 49.79mmol) and stir at low temperature for 1 hour. After adding 3.8 ml (49.79 mmol) of DMF at -78 ° C, the mixture is stirred for 1 hour. After the reaction was completed, 1M HCl was added at 0 ° C., washed with distilled water, extracted with EA, dried over MgSO 4 , dried over a rotary evaporator, and then purified by column chromatography to obtain compound H 6g (72%). .

화합물 compound JJ 의 제조Manufacture

100 ml 둥근바닥 플라스크에 화합물 I 6.7g (28.72mmol)을 넣고 THF 50ml를 첨가한 후 0℃로 냉각시킨다. NaBH4 1.4g(37.34mmol)과 MeOH 6ml 첨가한 뒤 실온에서 2시간동안 교반한다. 반응이 끝나면 증류수로 씻어주고 EA로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 J 6g (89%)을 얻었다. 6.7 g (28.72 mmol) of Compound I were added to a 100 ml round bottom flask, and 50 ml of THF was added, followed by cooling to 0 ° C. 1.4 g (37.34 mmol) of NaBH 4 and 6 ml of MeOH were added, followed by stirring at room temperature for 2 hours. After the reaction, the mixture was washed with distilled water, extracted with EA, dried over MgSO 4 , dried over MgSO 4 , solvent was removed by rotary evaporation, and purified by column chromatography to obtain Compound J (6 g, 89%).

화합물 compound KK 의 제조Manufacture

50 ml 둥근바닥 플라스크에 화합물 J 6g (25.50mmol)을 넣고 P(OEt)3 8.5ml(51.0mmol)를 첨가한 후 0℃로 냉각시킨다. I2 6.4g(25.50mmol)천천히 첨가한 뒤 0℃에서10분간 교반한다. 이 후 120℃ 로 밤새 환류시킨다. 반응이 끝나면 디스틸레이션으로 P(OEt)3를 제거하고, 증류수로 씻어주고 EA로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 K 5.1g (59%)를 얻었다.6 g (25.50 mmol) of Compound J was added to a 50 ml round bottom flask, and 8.5 ml (51.0 mmol) of P (OEt) 3 was added, followed by cooling to 0 ° C. 6.4 g (25.50 mmol) of I 2 is slowly added and stirred at 0 ° C. for 10 minutes. This is then refluxed at 120 ° C. overnight. After the reaction was completed, P (OEt) 3 was removed by distillation, washed with distilled water, extracted with EA, the organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and purified by column chromatography. Compound K 5.1 g (59%) was obtained.

화합물 compound 6565 의 제조Manufacture

250 ml 둥근바닥 플라스크에 화합물 H 3g (11.98mmol)과 화합물 K 4.8g(14.38mmol)를 넣은 후 진공 건조 시킨 뒤 아르곤 가스를 채운다. THF 100ml를 첨가한 후 0℃로 냉각시킨다. 1M KO(t-Bu) 14.3ml(14.38mmol)를 천천히 넣은 후 실온에서 3시간동안 교반시킨다. 반응이 끝나면 증류수로 씻어주고 EA로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 65 3.3g (61%)를 얻었다.3 g (11.98 mmol) of Compound H and 4.8 g (14.38 mmol) of Compound K were added to a 250 ml round bottom flask, followed by vacuum drying and filling with argon gas. 100 ml of THF is added and then cooled to 0 ° C. 14.3 ml (14.38 mmol) of 1M KO (t-Bu) was added slowly, followed by stirring at room temperature for 3 hours. After completion of the reaction, the mixture was washed with distilled water, extracted with EA, dried over MgSO 4 , dried over MgSO 4 , solvent was removed by rotary evaporation, and purified by column chromatography to obtain compound 65 (3.3 g, 61%).

1H NMR(CDCl3, 200MHz) δ = 0.9(6H, m), 1.91(4H, m), 6.95(2H, m), 7.28(1H, m), 7.35~7.38(2H, m), 7.54~7.6(5H, m), 7.71(1H, m), 7.78(1H, m), 7.87(2H, m), 7.98(1H, m), 8.06~8.1(2H, m), 8.3(2H, m) 1 H NMR (CDCl 3 , 200 MHz) δ = 0.9 (6H, m), 1.91 (4H, m), 6.95 (2H, m), 7.28 (1H, m), 7.35-7.38 (2H, m), 7.54- 7.6 (5H, m), 7.71 (1H, m), 7.78 (1H, m), 7.87 (2H, m), 7.98 (1H, m), 8.06-8.1 (2H, m), 8.3 (2H, m)

상기 제조예 1 내지 4의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 62을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to 62 were prepared using the methods of Preparation Examples 1 to 4, and 1 H NMR and MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.

[표 1]TABLE 1

Figure 112009033388514-PAT00027
Figure 112009033388514-PAT00027

Figure 112009033388514-PAT00028
Figure 112009033388514-PAT00028

Figure 112009033388514-PAT00029
Figure 112009033388514-PAT00029

[실시예 1-7] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 1-7 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention

본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15 Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 하기 구조의 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)을 넣고, 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 2-TNATA를 증발시켜 ITO 기판 상에 60 nm 두께의 정공주입층을 증착하였다.An OLED device having a structure using the light emitting material of the present invention was produced. First, a transparent electrode ITO thin film (15? It was used after. Next, an ITO substrate is installed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2) having the structure -TNATA), evacuated until the vacuum in the chamber reached 10 -6 torr, and then applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate.

이어서, 진공 증착 장비 내의 다른 셀에 하기구조 N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.The NPB -diphenyl-4,4'-diamine into the (NPB), by applying a current to the cell - Then, to another cell of the vacuum vapor-deposit device structure, N, N 'N, N -bis (α-naphthyl)' A 20 nm thick hole transport layer was deposited on the hole injection layer by evaporation.

Figure 112009033388514-PAT00030
Figure 112009033388514-PAT00030

정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 하기 구조의 DNA(실시예 1 내지 4) 또는 H-33(실시예 5 내지 7)를 넣고, 또 다른 셀에는 도판트로서 본 발명에 따른 화합물을 각각 넣은 후, 증착 속도를 100:1 로 하여 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. In one cell of the vacuum deposition equipment, DNA (Examples 1 to 4) or H-33 (Examples 5 to 7) having the following structure was put as a host, and in another cell, the compound according to the present invention was put as a dopant, respectively. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer at a deposition rate of 100: 1.

Figure 112009033388514-PAT00031
Figure 112009033388514-PAT00031

이어서 전자전달층으로써 하기 구조의 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 하기 구조의 화 합물 lithium quinolate (Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다. Subsequently, tris (8-hydroxyquinoline) -aluminum (III) (Alq) having a structure of 20 nm in thickness was deposited as an electron transport layer, and then a lithium quinolate (Liq) having a structure of 1 to 2 nm was formed as an electron injection layer. After deposition to a thickness, using a different vacuum deposition equipment to deposit an Al cathode to a thickness of 150 nm to produce an OLED.

Figure 112009033388514-PAT00032
Figure 112009033388514-PAT00032

재료 별로 각 화합물은 10-6torr 하에서 진공승화 정제하여 OLED 발광재료로 사용하였다.For each material, each compound was used as an OLED light emitting material by vacuum sublimation purification under 10 -6 torr.

[비교예 1] 종래의 발광 재료를 이용한 OLED 소자 제작Comparative Example 1 Fabrication of OLED Device Using Conventional Light-Emitting Material

상기 실시예 1과 동일한 방법으로 정공주입층, 정공전달층을 형성시킨 후, 상기 진공 증착 장비 내의 다른 셀에 청색 발광 재료인 DNA를 넣고, 또 다른 셀에는 청색 발광 재료인 하기 구조의 화합물 A를 각각 넣은 후, 증착 속도를 100:1 로 하여 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, DNA, which is a blue light emitting material, was placed in another cell in the vacuum deposition apparatus, and compound A having the following structure, which was a blue light emitting material, was added to another cell. After each addition, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer at a deposition rate of 100: 1.

Figure 112009033388514-PAT00033
Figure 112009033388514-PAT00033

이어서 실시예 1과 동일한 방법으로 전자전달층과 전자주입층을 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다.Subsequently, an electron transport layer and an electron injection layer were deposited in the same manner as in Example 1, and then another OLED was manufactured by depositing an Al cathode to a thickness of 150 nm using another vacuum deposition equipment.

[비교예 2] 종래의 발광 재료를 이용한 OLED 소자 제작Comparative Example 2 Fabrication of OLED Device Using Conventional Light-Emitting Material

실시예 1과 동일한 방법으로 정공주입층, 정공전달층을 형성시킨 후, 상기 진공 증착 장비 내의 다른 셀에 청색 발광 재료인 DNA을 넣고, 또 다른 셀에는 다른 청색 발광 재료인 하기 구조의 화합물 B를 각각 넣은 후, 증착 속도를 100:1 로 하여 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed in the same manner as in Example 1, DNA, which is a blue light emitting material, was placed in another cell in the vacuum deposition apparatus, and another cell, Compound B , having the following structure After each addition, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer at a deposition rate of 100: 1.

Figure 112009033388514-PAT00034
Figure 112009033388514-PAT00034

이어서 실시예 1과 동일한 방법으로 전자전달층과 전자주입층을 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다.Subsequently, an electron transport layer and an electron injection layer were deposited in the same manner as in Example 1, and then another OLED was manufactured by depositing an Al cathode to a thickness of 150 nm using another vacuum deposition equipment.

상기 실시예 1-7과 비교예 1-2에서 제조된 본 발명에 따른 유기 발광 화합물과 종래의 발광 화합물을 함유하는 OLED 소자의 발광 효율을 각각 1,000 cd/m2에서 측정하여 하기 표 2에 나타내었다. Below with the Examples 1-7 and Comparative Examples 1-2 are measured at 1,000 cd / m 2 light emission efficiency of the OLED device containing the organic light-emitting compound and a conventional electroluminescent compound according to the present invention in the manufacture shown in Table 2 It was.

[표 2]TABLE 2

Figure 112009033388514-PAT00035
Figure 112009033388514-PAT00035

상기 표 2에 나타난 바와 같이, 본 발명의 유기 발광 화합물들은 종래의 발광 화합물보다 진한 청색 및 높은 효율을 구현할 수 있음을 알 수 있었다. 특히, 화합물 2의 경우에는 종래의 발광재료(화합물B)에 대하여 효율이 38%이상 향상된 것을 확인할 수 있었다. 이상에서와 같이 본 발명의 유기 발광 화합물은 진한 청색 및 고효율의 청색 발광 재료로 사용될 수 있고, 기존의 풀컬러 OLED의 휘도 및 소비전력 면에서 커다란 장점을 가지고 있다.As shown in Table 2, it was found that the organic light emitting compounds of the present invention can realize a darker blue color and a higher efficiency than the conventional light emitting compounds. In particular, in the case of compound 2, it was confirmed that the efficiency was improved by 38% or more with respect to the conventional light emitting material (compound B). As described above, the organic light emitting compound of the present invention can be used as a dark blue and high efficiency blue light emitting material, and has a great advantage in terms of brightness and power consumption of the conventional full color OLED.

Claims (10)

하기 화학식 1로 표시되는 유기 발광 화합물.An organic light emitting compound represented by Formula 1 below. [화학식 1][Formula 1]
Figure 112009033388514-PAT00036
Figure 112009033388514-PAT00036
 [상기 화학식 1에서, A는 수소 또는
Figure 112009033388514-PAT00037
이며;[In Formula 1, A is hydrogen or
Figure 112009033388514-PAT00037
Is; Ar1 및 Ar2는 서로 독립적으로 화학결합이거나 (C6-C60)아릴렌 또는 N, O 또는 S로부터 선택된 하나 이상의 헤테로 원자를 포함하는 (C2-C60)헤테로아릴렌이고, 상기 헤테로아릴렌의 탄소원자는 Se로 더 치환될 수 있으며;Ar 1 and Ar 2 are independently (C6-C60) arylene chemically bonded to each other or (C2-C60) heteroarylene containing at least one hetero atom selected from N, O or S, and a carbon source of the heteroarylene Can be further substituted with Se; Z1 내지 Z5 중 적어도 하나 및 Z11 내지 Z15 중 적어도 하나는 질소 원자이고, 나머지는 탄소 원자이며, 상기 질소 원자의 경우에는 치환기가 존재하지 않고;At least one of Z 1 to Z 5 and at least one of Z 11 to Z 15 is a nitrogen atom, the remainder is a carbon atom, and in the case of the nitrogen atom there is no substituent; R1 내지 R5 및 R11 내지 R15는 서로 독립적으로 수소, 중수소, (C1-C60)알킬, (C3-C60)사이클로알킬, (C6-C60)아릴, (C2-C60)헤테로아릴, (C1-C60)알콕시, (C6-C60)아릴옥시, 모노 또는 디(C1-C60)알킬아미노, 모노 또는 디(C6-C60)아릴아미노, (C6-C60)아르(C1-C60)알킬아미노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴이고, 상기 R1 내지 R5 또는 R11 내지 R15는 각각 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 O, S 또는 NR21로 더 치환될 수 있고, 상기 알케닐렌의 CH는 N으로 더 치환될 수 있고;R 1 to R 5 and R 11 to R 15 are each independently hydrogen, deuterium, (C1-C60) alkyl, (C3-C60) cycloalkyl, (C6-C60) aryl, (C2-C60) heteroaryl, ( C1-C60) alkoxy, (C6-C60) aryloxy, mono or di (C1-C60) alkylamino, mono or di (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkylamino, Tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl, wherein R 1 to R 5 or R 11 to R 15 are each adjacent substituents And (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form a fused ring, wherein the carbon atom of the alkylene is further substituted with O, S or NR 21 . And the CH of the alkenylene may be further substituted with N; R21은 수소, 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 모폴리노, 티오모폴리노, 피페리디노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C3-C60)사이클로알킬, 아다만틸, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, (C1-C60)트리알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴이고;R 21 is one selected from hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, morpholino, thiomorpholino, piperidino, N, O and S 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, adamantyl, halogen, cyano, (C6-C60) aryl, (C2-C60) heteroaryl, (C1-C60) ) Trialkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl; X 및 Y는 서로 독립적으로 화학결합이거나, -(CR31R32)n-, -N(R33)-, -Si(R34)(R35)-, -O-, -S-, -Se-, -P(R36)-, 또는 -(R37)C=C(R38)-이며, n은 1 내지 4의 정수이고;X and Y are each independently a chemical bond or-(CR 31 R 32 ) n- , -N (R 33 )-, -Si (R 34 ) (R 35 )-, -O-, -S-,- Se-, -P (R 36 )-, or-(R 37 ) C = C (R 38 )-, n is an integer from 1 to 4; R31 내지 R38은 서로 독립적으로 수소, 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 모폴리노, 티오모폴리노, 피페리디노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C3-C60)사이클로알킬, 아다만틸, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴, 트리(C6-C60)아릴실릴이거나, R31과 R32, R34와 R35 또는 R37과 R38은 서로 독립적으로 융합고리를 포함하거나 포함하지 않 는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 스피로고리 또는 융합고리를 형성할 수 있고;R 31 to R 38 are independently of each other hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, morpholino, thiomorpholino, piperidino, N, 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, adamantyl, halogen, cyano, (C6-C60) aryl, (C2-C60) hetero, including one or more selected from O and S Aryl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, or R 31 and R 32 , R 34 and R 35 Or R 37 and R 38 may be independently linked to each other with (C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring to form a spirogory or fused ring; Ar1 및 Ar2의 아릴렌 또는 헤테로아릴렌, R1 내지 R5, R11 내지 R15, R21 및 R31 내지 R38의 알킬, 사이클로알킬, 아릴, 헤테로아릴, 알콕시, 아릴옥시, 알킬아미노, 아릴아미노, 아르알킬아미노, 트리알킬실릴, 디알킬아릴실릴 또는 트리아릴실릴은 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로사이클로알킬, (C3-C60)사이클로알킬, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, (C6-C60)아르(C1-C60)알킬, (C1-C60)알킬(C6-C60)아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로부터 선택되는 하나 이상의 치환기가 더 치환될 수 있다.]Arylene or heteroarylene of Ar 1 and Ar 2 , R 1 to R 5 , R 11 to R 15 , R 21 and R 31 to R 38 alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkyl Amino, arylamino, aralkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl are deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, piperidino, 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, halogen, cyano, (C6-C60) aryl containing one or more selected from morpholino, thiomorpholino, N, O and S , (C2-C60) heteroaryl, (C6-C60) ar (C1-C60) alkyl, (C1-C60) alkyl (C6-C60) aryl, tri (C1-C60) alkylsilyl, di (C1-C60) One or more substituents selected from alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted.] 제 1항에 있어서,The method of claim 1, 하기 화학식 2 또는 3으로 표시되는 유기 발광 화합물.An organic light emitting compound represented by the following Chemical Formula 2 or 3. [화학식 2][Formula 2]
Figure 112009033388514-PAT00038
Figure 112009033388514-PAT00038
 [화학식 3](3)
Figure 112009033388514-PAT00039
Figure 112009033388514-PAT00039
 [상기 화학식 2 및 3에서, X, Y, Ar1, Ar2, Z1 내지 Z5, Z11 내지 Z15, R1 내지 R15 및 R11 내지 R15는 상기 청구항 제1항에서의 정의와 동일하다.][In Formulas 2 and 3, X, Y, Ar 1 , Ar 2 , Z 1 to Z 5 , Z 11 to Z 15 , R 1 to R 15 and R 11 to R 15 are the definitions in claim 1 above. Is the same as.] 제 1항에 있어서,The method of claim 1, 상기 Ar1 및 Ar2는 서로 독립적으로 화학결합이거나 하기 구조에서 선택되는 아릴렌 또는 헤테로아릴렌인 것을 특징으로 하는 유기 발광 화합물.The Ar 1 and Ar 2 is an organic light emitting compound, characterized in that independently of each other or arylene or hetero arylene selected from the following structure.
Figure 112009033388514-PAT00040
Figure 112009033388514-PAT00040
 [R41은 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로사이클로알킬, (C3-C60)사이클로알킬, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, (C6-C60)아르(C1-C60)알킬, (C1-C60)알킬(C6-C60)아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴이고, m은 0 내지 4의 정수이다.][R 41 is one or more selected from deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, piperidino, morpholino, thiomorpholino, N, O and S 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, halogen, cyano, (C6-C60) aryl, (C2-C60) heteroaryl, (C6-C60) ar (C1-) C60) alkyl, (C1-C60) alkyl (C6-C60) aryl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl , m is an integer of 0 to 4.] 제 2항에 있어서,3. The method of claim 2, 상기
Figure 112009033388514-PAT00041
는 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.remind
Figure 112009033388514-PAT00041
Is an organic light emitting compound, characterized in that selected from the following structure.
Figure 112009033388514-PAT00042
Figure 112009033388514-PAT00042
 [R31 내지 R38은 서로 독립적으로 수소, 중수소, (C1-C60)알킬, 할로(C1-C60) 알킬, (C1-C60)알콕시, 모폴리노, 티오모폴리노, 피페리디노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C3-C60)사이클로알킬, 아다만틸, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴, 트리(C6-C60)아릴실릴고; 상기 R21 내지 R28의 알킬, 사이클로알킬, 아릴, 헤테로아릴, 알콕시, 트리알킬실릴, 디알킬아릴실릴 또는 트리아릴실릴은 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로사이클로알킬, (C3-C60)사이클로알킬, 할로겐, 시아노, (C6-C60)아릴, (C2-C60)헤테로아릴, (C6-C60)아르(C1-C60)알킬, (C1-C60)알킬(C6-C60)아릴, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로부터 선택되는 하나 이상의 치환기가 더 치환될 수 있다.][R 31 to R 38 are independently of each other hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, morpholino, thiomorpholino, piperidino, N 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, adamantyl, halogen, cyano, (C6-C60) aryl, (C2-C60) containing at least one selected from Heteroaryl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl; Alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 21 to R 28 may be deuterium, (C 1 -C 60) alkyl, halo (C 1 -C 60) alkyl, ( C6-C60) 5- to 6-membered heterocycloalkyl, (C3-C60) cycloalkyl, halogen, including one or more selected from alkoxy, piperidino, morpholino, thiomorpholino, N, O and S , Cyano, (C6-C60) aryl, (C2-C60) heteroaryl, (C6-C60) ar (C1-C60) alkyl, (C1-C60) alkyl (C6-C60) aryl, tri (C1-C60 One or more substituents selected from alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted.] 제 2항에 있어서,3. The method of claim 2, 상기
Figure 112009033388514-PAT00043
및
Figure 112009033388514-PAT00044
는 서로 독립적으로 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.remind
Figure 112009033388514-PAT00043
And
Figure 112009033388514-PAT00044
Are independently selected from the following structures:
Figure 112009033388514-PAT00045
Figure 112009033388514-PAT00045
 제 1항 내지 제 5항에서 선택되는 어느 한 항에 따른 유기 발광 화합물을 포함하는 것을 특징으로 하는 유기 발광 소자.An organic light emitting device comprising the organic light emitting compound according to any one of claims 1 to 5. 제 6항에 있어서,The method of claim 6, 상기 유기 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어져 있으며, 상기 유기물층은 상기 유기 발광 화합물을 하나 이상과 하기 화학식 4 또는 화학식 5에서 선택되는 호스트 하나 이상을 포함하는 것을 특징으로 하는 유기 발광 소자.The organic light emitting diode includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound and at least one host selected from Formula 4 or Formula 5 below. Organic light emitting device. [화학식 4][Formula 4] (Ar11)c-L1-(Ar12)d (Ar 11 ) c -L 1- (Ar 12 ) d [화학식 5][Chemical Formula 5] (Ar13)e-L2-(Ar14)f (Ar 13 ) e -L 2- (Ar 14 ) f [상기 화학식 4 및 화학식 5에서,[In Formula 4 and Formula 5, L1는 (C6-C60)아릴렌 또는 (C4-C60)헤테로아릴렌이고;L 1 is (C6-C60) arylene or (C4-C60) heteroarylene; L2는 안트라세닐렌이며;L 2 is anthracenylene; Ar11 내지 Ar14은 서로 독립적으로 수소, 중수소, (C1-C60)알킬, (C1-C60)알콕시, 할로겐, (C4-C60)헤테로아릴, (C5-C60)시클로알킬 또는 (C6-C60)아릴이고, 상기 Ar11 내지 Ar14의 시클로알킬, 아릴 또는 헤테로아릴은 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, (C3-C60)시클로알킬, 할로겐, 시아노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로 이루어진 군으로부터 선택된 하나 이상이 치환되거나 치환되지 않은 (C6-C60)아릴 또는 (C4-C60)헤테로아릴, 중수소, (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, (C3-C60)시클로알킬, 할로겐, 시아노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로 이루어지는 군에서 선택되는 하나 이상의 치환기가 더 치환될 수 있고;Ar 11 to Ar 14 are each independently hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) Aryl, and the cycloalkyl, aryl or heteroaryl of Ar 11 to Ar 14 is deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, (C3-C60) cycloalkyl, One or more selected from the group consisting of halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl is unsubstituted or substituted (C6-C60) aryl or (C4-C60) heteroaryl, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyan At least one substituent selected from the group consisting of: no, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted; c, d, e 및 f는 서로 독립적으로 0 내지 4의 정수이다.]c, d, e and f are each independently an integer from 0 to 4.] 제 7항에 있어서,The method of claim 7, wherein 상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물 또는 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속을 더 포함하는 것을 특징으로 하는 유기 발광 소자. At least one compound selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds, or organic metals of lanthanide-based metals and d-transition elements in the organic layer The organic light emitting device further comprises at least one metal selected from the group. 제 7항에 있어서,The method of claim 7, wherein 상기 유기물층에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 발광 소자.An organic light emitting device that emits white light by simultaneously including one or more organic light emitting layers emitting blue, red, or green light in the organic material layer. 제 7항에 있어서,The method of claim 7, wherein 상기 유기물층은 발광층 및 전하생성층을 포함하는 것을 특징으로 하는 유기 발광 소자.The organic material layer is an organic light emitting device comprising a light emitting layer and a charge generating layer.
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