KR20110121147A - 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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KR20110121147A
KR20110121147A KR1020100040610A KR20100040610A KR20110121147A KR 20110121147 A KR20110121147 A KR 20110121147A KR 1020100040610 A KR1020100040610 A KR 1020100040610A KR 20100040610 A KR20100040610 A KR 20100040610A KR 20110121147 A KR20110121147 A KR 20110121147A
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South Korea
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alkyl
aryl
light emitting
heteroaryl
cycloalkyl
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KR1020100040610A
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Korean (ko)
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김영길
김치식
조영준
권혁주
김성민
김봉옥
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다우어드밴스드디스플레이머티리얼 유한회사
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Priority to KR1020100040610A priority Critical patent/KR20110121147A/en
Priority to CN201180031554.2A priority patent/CN102958906B/en
Priority to JP2013507866A priority patent/JP5782503B2/en
Priority to PCT/KR2011/002526 priority patent/WO2011136484A1/en
Priority to TW100115068A priority patent/TW201213308A/en
Publication of KR20110121147A publication Critical patent/KR20110121147A/en

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  • Electroluminescent Light Sources (AREA)
  • Furan Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Quinoline Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

PURPOSE: A novel organic light-emitting compound is provided to ensure excellent luminous efficiency and lifetime compared with existing dopant materials and proper color coordinate. CONSTITUTION: A novel organic light-emitting compound is represented by chemical formula 1. In chemical formula 1, Ar1-Ar4 are (C3-C30) cycloalkyl, (C2-C30) heteroaryl including one selected from N, O and S, 5-7-membered heterocycloalkyl including one selected from N, O and S, (C3-C30) cycloalkyl, adamantyl, or (C7-C30) bicycloalkyl; and R1~R6 and R11~R13 are hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C6-C30) aryl, (C2-C30) heteroaryl, (C1-C30) alkoxy, (C6-C30) aryloxy, mono or di(C1-C30) arylamino, mono or di(C6-C30) alkylamino, (C6-C30)aryl(C1-C30) alkylamino, tri (C1-C30) alkylsilyl, di(C1-C30)alkyl(C6-C30) arylsilyl, or tri(C6-C30) arylsilyl.

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. In organic EL devices, the most important factor that determines the performance of light emission efficiency, lifetime, etc. is a light emitting material. Some characteristics required for such a light emitting material include high quantum fluorescence yield in solid state, and mobility of electrons and holes. It should be high, not easily decomposed during vacuum deposition, and form a stable 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 pat00001
Figure pat00001

따라서, 본 발명자들은 종래의 문제점을 해결하기 위하여 노력한 결과, 발광효율이 뛰어나고 수명이 획기적으로 개선된 유기 발광 소자를 실현하기 위한 새로운 발광 화합물을 발명하게 되었다. 본 발명의 목적은 상기한 문제점들을 해결하기 위하여 기존의 도판트 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물 및 이를 발광재료로서 채용하는 고효율 및 장수명의 유기 발광 소자를 제공하는 것이다. Accordingly, the present inventors have made efforts to solve the conventional problems, and have thus invented a new light emitting compound for realizing an organic light emitting device having excellent luminous efficiency and a markedly improved lifetime. An object of the present invention is to solve the above problems, the luminous efficiency and device life is better than the conventional dopant material, an excellent organic light emitting compound having an appropriate color coordinate and a high efficiency and long life organic light emitting device employing it as a light emitting material To provide.

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

[화학식 1][Formula 1]

Figure pat00002
Figure pat00002

[상기 화학식 1에서,[In Formula 1,

Ar1 내지 Ar4는 서로 독립적으로 (C6-C30)아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 (C2-C30)헤테로아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 아다만틸, (C7-C30)바이사이클로알킬 또는

Figure pat00003
이거나, Ar1와 Ar2는 및 Ar3와 Ar4는 각각 방향족고리 또는 헤테로방향족고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 NR21, O, S 또는 SiR22R23으로 더 치환될 수 있고;Ar 1 to Ar 4 are each independently a 5 member comprising one or more selected from (C 2 -C 30) heteroaryl, N, O and S, including one or more selected from (C 6 -C 30) aryl, N, O and S To 7 membered heterocycloalkyl, (C3-C30) cycloalkyl, adamantyl, (C7-C30) bicycloalkyl or
Figure pat00003
Or Ar 1 and Ar 2 and Ar 3 and Ar 4 are each connected to (C3-C30) alkylene or (C3-C30) alkenylene with or without aromatic ring or heteroaromatic ring to form a fused ring. May be further substituted with NR 21 , O, S or SiR 22 R 23 ;

R1 내지 R6 및 R11 내지 R13은 각각 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알콕시, (C6-C30)아릴옥시, 모노 또는 디(C1-C30)알킬아미노, 모노 또는 디(C6-C30)아릴아미노, (C6-C30)아릴(C1-C30)알킬아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이고; R 1 to R 6 and R 11 to R 13 are each independently hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C6-C30) aryl, (C2-C30) heteroaryl, (C1- C30) alkoxy, (C6-C30) aryloxy, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, (C6-C30) aryl (C1-C30) alkylamino, tri ( C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl;

R21 내지 R23은 서로 독립적으로 (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, 모폴리노, 티오모폴리노, 피페리디노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 아다만틸, 할로겐, 시아노, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)트리알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이거나, R22와 R23은 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며;R 21 to R 23 are independently of each other from (C 1 -C 30) alkyl, halo (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, morpholino, thiomorpholino, piperidino, N, O and S 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, adamantyl, halogen, cyano, (C6-C30) aryl, (C2-C30) heteroaryl, (C1) comprising one or more selected -C30) trialkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl, or R 22 and R 23 with or without fused ring (C3-C30) May be linked to alkylene or (C3-C30) alkenylene to form a fused ring;

상기 R1 내지 R6의 알킬기, 사이클로알킬기, 아릴, 헤테로아릴, 알콕시, 아릴옥시, 알킬아미노, 아릴아미노, 아릴알킬아미노, 트리알킬실릴, 디알킬아릴실릴 또는 트리아릴실릴; Ar1 내지 Ar4의 아릴, 헤테로아릴, 헤테로사이클로알킬, 사이클로알킬, 아다만틸 또는 바이사이클로알킬; Ar1와 Ar2가 Ar3와 Ar4가 각각 연결되어 형성된 융합고리; R21 내지 R23의 알킬, 할로알킬, 알콕시, 모폴리노, 티오모폴리노, 피페리디노, 헤테로시클로알킬, 시클로알킬, 아다만틸, 아릴, 헤테로아릴, 트리알킬실릴, 디알킬아릴실릴 또는 트리아릴실릴은 (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, (C1-C30)알킬티오, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 할로겐, 시아노, 나이트로, 하이드록시, (C6-C30)아릴, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C2-C30)헤테로아릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴로부터 선택되는 하나 이상의 치환기가 더 치환될 수 있다.]The alkyl group, cycloalkyl group, aryl, heteroaryl, alkoxy, aryloxy, alkylamino, arylamino, arylalkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 1 to R 6 ; Aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar 1 to Ar 4 ; A fused ring formed by Ar 1 and Ar 2 connected to Ar 3 and Ar 4 , respectively; Alkyl, haloalkyl, alkoxy, morpholino, thiomorpholino, piperidino, heterocycloalkyl, cycloalkyl, adamantyl, aryl, heteroaryl, trialkylsilyl, dialkylarylsilyl of R 21 to R 23 Or triarylsilyl is (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C1-C30) alkylthio, piperidino, morpholino, thiomorpholino, N, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, halogen, cyano, nitro, hydroxy, (C6-C30) aryl, (C6-C30) comprising one or more selected from O and S ) Aryloxy, (C6-C30) arylthio, (C2-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, tri (C1- One or more substituents selected from C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl may be further substituted.]

본 발명에 기재된 “알킬”, “알콕시” 및 그 외 “알킬”부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다. 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. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트라이페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P, P(=O), Si 및 Se로부터 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. 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, 퀴녹살리닐, 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.Substituents comprising the "alkyl", "alkoxy" and other "alkyl" moieties described herein include both straight and pulverized forms. "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. 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. "Heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P, P (= O), Si and Se as aromatic ring skeleton atoms, and the remaining aromatic ring skeletons. Means an aryl group whose atoms are carbon, 5-6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. 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, Quinolizinyl, 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.

또한, 본 발명에 기재되어 있는 “(C1-C30)알킬, (C1-C30)알콕시, 모노 또는 디(C1-C30)알킬아미노, (C6-C30)아릴(C1-C30)알킬아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 할로(C1-C30)알킬, (C1-C30)알킬티오, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴” 등의 알킬은 탄소수 1 내지 20개로 제한될 수 있고, 탄소수 1 내지 10개로 제한될 수 있다. “(C6-C30)아릴, 모노 또는 디(C6-C30)아릴아미노, (C6-C30)아릴(C1-C30)알킬아미노, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴”등의 아릴은 탄소수 6 내지 20개로 제한될 수 있고, 탄소수 6 내지 12개로 제한될 수 있다. “(C3-C30)헤테로아릴”의 헤테로아릴은 탄소수 4 내지 20개로 제한될 수 있고, 탄소수 4 내지 12개로 제한될 수 있다. “(C3-C30)시클로알킬”의 시클로알킬은 탄소수 3 내지 20개로 제한될 수 있고, 탄소수 3 내지 7개로 제한될 수 있다. “(C3-C30)알킬렌 또는 알케닐렌”의 알킬렌 또는 알케닐렌은 탄소수 3 내지 20개로 제한될 수 있고, 탄소수 3 내지 10개로 제한될 수 있다.Also described herein are "(C1-C30) alkyl, (C1-C30) alkoxy, mono or di (C1-C30) alkylamino, (C6-C30) aryl (C1-C30) alkylamino, tri ( C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, halo (C1-C30) alkyl, (C1-C30) alkylthio, (C6-C30) ar (C1-C30) alkyl Alkyl such as (C1-C30) alkyl (C6-C30) aryl ”may be limited to 1 to 20 carbon atoms, and may be limited to 1 to 10 carbon atoms. “(C6-C30) aryl, mono or di (C6-C30) arylamino, (C6-C30) aryl (C1-C30) alkylamino, di (C1-C30) alkyl (C6-C30) arylsilyl, tri ( C6-C30) arylsilyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl ”, etc. The aryl of may be limited to 6 to 20 carbon atoms, it may be limited to 6 to 12 carbon atoms. Heteroaryl of "(C3-C30) heteroaryl" may be limited to 4 to 20 carbon atoms, it may be limited to 4 to 12 carbon atoms. The cycloalkyl of "(C3-C30) cycloalkyl" may be limited to 3 to 20 carbon atoms, and may be limited to 3 to 7 carbon atoms. Alkylene or alkenylene of “(C3-C30) alkylene or alkenylene” may be limited to 3 to 20 carbon atoms, and may be limited to 3 to 10 carbon atoms.

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

[화학식 2][Formula 2]

Figure pat00004
Figure pat00004

[상기 R5 및 R6은 각각 독립적으로 수소, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이고;[Wherein R 5 and R 6 are each independently hydrogen, (C6-C30) aryl or (C2-C30) heteroaryl;

Ar1 내지 Ar4는 서로 독립적으로 (C6-C30)아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 (C2-C30)헤테로아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 아다만틸, (C7-C30)바이사이클로알킬 또는

Figure pat00005
이거나, Ar1와 Ar2는 및 Ar3와 Ar4는 각각 방향족고리 또는 헤테로방향족고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 NR21, O, S 또는 SiR22R23으로 더 치환될 수 있고;Ar 1 to Ar 4 are each independently a 5 member comprising one or more selected from (C 2 -C 30) heteroaryl, N, O and S, including one or more selected from (C 6 -C 30) aryl, N, O and S To 7 membered heterocycloalkyl, (C3-C30) cycloalkyl, adamantyl, (C7-C30) bicycloalkyl or
Figure pat00005
Or Ar 1 and Ar 2 and Ar 3 and Ar 4 are each connected to (C3-C30) alkylene or (C3-C30) alkenylene with or without aromatic ring or heteroaromatic ring to form a fused ring. May be further substituted with NR 21 , O, S or SiR 22 R 23 ;

R21 내지 R23은 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이거나, R22와 R23은 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며;R 21 to R 23 are independently of each other (C1-C30) alkyl or (C6-C30) aryl, or R 22 and R 23 are (C3-C30) alkylene or (C3-C30) with or without fused ring May be linked to alkenylene to form a fused ring;

상기 R5 및 R6의 아릴 또는 헤테로아릴; Ar1 내지 Ar4의 아릴, 헤테로아릴, 헤테로사이클로알킬, 사이클로알킬, 아다만틸 또는 바이사이클로알킬; Ar1와 Ar2가 Ar3와 Ar4가 각각 연결되어 형성된 융합고리; R21 내지 R23의 알킬 또는 아릴은 (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, (C1-C30)알킬티오, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 할로겐, 시아노, 나이트로, 하이드록시, (C6-C30)아릴, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C2-C30)헤테로아릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴로부터 선택되는 하나 이상의 치환기가 더 치환될 수 있다.]Aryl or heteroaryl of R 5 and R 6 ; Aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar 1 to Ar 4 ; A fused ring formed by Ar 1 and Ar 2 connected to Ar 3 and Ar 4 , respectively; Alkyl or aryl of R 21 to R 23 is (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C1-C30) alkylthio, piperidino, morpholino, thiomo 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, halogen, cyano, nitro, hydroxy, (C6-C30) aryl containing one or more selected from polyno, N, O and S , (C6-C30) aryloxy, (C6-C30) arylthio, (C2-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl One or more substituents selected from tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl may be further substituted.]

또한 상기 Ar1와 Ar2는 및 Ar3와 Ar4가 각각 독립적으로 알킬렌 또는 알케닐렌으로 연결되어 형성된

Figure pat00006
및
Figure pat00007
는 서로 독립적으로 하기 구조에서 선택되나, 이에 한정되지는 않는다.In addition, Ar 1 And Ar 2 And And Ar 3 And Ar 4 It is formed by being independently connected to alkylene or alkenylene
Figure pat00006
And
Figure pat00007
Are independently selected from the following structures, but are not limited thereto.

Figure pat00008
Figure pat00008

[R21 내지 R25은 서로 독립적으로 (C1-C60)알킬 또는 (C6-C60)아릴이다.]
[R 21 to R 25 are independently from each other (C1-C60) alkyl or (C6-C60) aryl.]

더욱 구체적으로, 상기 Ar1 내지 Ar4는 서로 독립적으로 하기 구조에서 선택되어지나, 이에 한정되는 것은 아니다.More specifically, Ar 1 to Ar 4 may be selected from the following structures independently from each other, but are not limited thereto.

Figure pat00009
Figure pat00009

Figure pat00010
Figure pat00010

Figure pat00011
Figure pat00011

Figure pat00012
Figure pat00012

Figure pat00013
Figure pat00013

Figure pat00014
Figure pat00014

Figure pat00015
Figure pat00015

Figure pat00016
Figure pat00016

Figure pat00017
Figure pat00017

Figure pat00018
Figure pat00018

Figure pat00019
Figure pat00019

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 pat00020
Figure pat00020

Figure pat00021
Figure pat00021

Figure pat00022
Figure pat00022

Figure pat00023
Figure pat00023

Figure pat00024
Figure pat00024

Figure pat00025
Figure pat00025

Figure pat00026
Figure pat00026

Figure pat00027
Figure pat00027

Figure pat00028
Figure pat00028

Figure pat00029
Figure pat00029

Figure pat00030
Figure pat00030

Figure pat00031
Figure pat00031

Figure pat00032
Figure pat00032

Figure pat00033
Figure pat00033

Figure pat00034
Figure pat00034

Figure pat00035
Figure pat00035

Figure pat00036
Figure pat00036

Figure pat00037
Figure pat00037

Figure pat00038
Figure pat00038

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 pat00039
Figure pat00039

[상기 반응식 1에서 Ar1 내기 Ar4 및 R1 내지 R6는 상기 화학식 1에서 정의한 바와 동일하다.][Ar 1 and Ar 4 and R 1 to R 6 in Scheme 1 are the same as defined in Formula 1.]

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 represented by 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 적용되는 호스트는 특별히 제한되지 않으나, 하기 화학식 3 또는 화학식 4로 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 one or more hosts 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 (3) or (4). 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 3](3)

(Ar11)a-L1-(Ar12)b (Ar 11 ) a -L 1- (Ar 12 ) b

[화학식 4][Formula 4]

(Ar13)c-L2-(Ar14)d (Ar 13 ) c -L 2- (Ar 14 ) d

[상기 화학식 3 및 화학식 4에서,[In Formula 3 and Formula 4,

L1는 (C6-C30)아릴렌 또는 (C4-C30)헤테로아릴렌이고;L 1 is (C6-C30) arylene or (C4-C30) heteroarylene;

L2는 안트라세닐렌이며;L 2 is anthracenylene;

Ar11 내지 Ar14은 서로 독립적으로 수소, 중수소, (C1-C30)알킬, (C1-C30)알콕시, 할로겐, (C4-C30)헤테로아릴, (C5-C30)시클로알킬 또는 (C6-C30)아릴이고, 상기 Ar11 내지 Ar14의 시클로알킬, 아릴 또는 헤테로아릴은 중수소, (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, (C3-C30)시클로알킬, 할로겐, 시아노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴로 이루어진 군으로부터 선택된 하나 이상이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 (C4-C30)헤테로아릴, 중수소, (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, (C3-C30)시클로알킬, 할로겐, 시아노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴로 이루어지는 군에서 선택되는 하나 이상의 치환기가 더 치환될 수 있고;Ar 11 to Ar 14 are each independently hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, (C4-C30) heteroaryl, (C5-C30) cycloalkyl or (C6-C30) Aryl, and the cycloalkyl, aryl or heteroaryl of Ar 11 to Ar 14 is deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C3-C30) cycloalkyl, One or more selected from the group consisting of halogen, cyano, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl is unsubstituted or substituted (C6-C30) aryl or (C4-C30) heteroaryl, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C3-C30) cycloalkyl, halogen, cyan At least one substituent selected from the group consisting of no, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl may be further substituted;

a, b, c 및 d는 서로 독립적으로 0 내지 4의 정수이다.]a, b, c and d 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 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 발광 소자를 형성할 수 있다. 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, an organic light emitting device that emits white light may be formed on the organic material layer by simultaneously including one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic light emitting compound. The compound emitting blue, green, or red light is exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.

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 안정화를 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. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive 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. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 발광 소자를 제작할 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. In addition, a white organic light emitting device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.

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.

[제조예 1]화합물 68의 제조Preparation Example 1 Preparation of Compound 68

Figure pat00040
Figure pat00040

화합물 B의 제조Preparation of Compound B

실온에서 화합물 A 20 g (96.05 mmol), 벤조일 퍼옥사이드 3.1 g (9.60 mmol, 75%), 니트로벤젠 300 mL 및 Br2 10.85 mL (211.3 mmol)을 혼합하고 120℃로 가열하였다. 3시간 후 실온으로 냉각하고 KOH 수용액으로 중성화시킨 후 MC로 추출하였다. 감압 증류 후 얻어진 고체를 EA로 재결정하여 화합물 B 20 g (56.92 %)을 얻었다.At room temperature 20 g (96.05 mmol) of Compound A, 3.1 g (9.60 mmol, 75%) of benzoyl peroxide, 300 mL of nitrobenzene and 10.85 mL of Br 2 (211.3 mmol) were mixed and heated to 120 ° C. After 3 hours, the mixture was cooled to room temperature, neutralized with aqueous KOH solution, and extracted with MC. After distillation under reduced pressure, the obtained solid was recrystallized with EA to obtain Compound B 20 g (56.92%).

화합물 C의 제조Preparation of Compound C

2-브로모나프탈렌 25.4 g (122.95 mmol)을 THF 1000 mL에 녹이고 -78℃에서 n-buLi (114.7 mmol, 2.5M in hexane)을 천천히 가하였다. 30분후 상온에서 교반시켰다. 30분후 화합물 B 14.1 g (40 mmol)를 가하였다. 12시간 교반후 증류수와 MC로 추출하였다. 유기층을 MgSO4로 건조시킨 다음 감압증류하여 용매를 제거하고 컬럼크로마토그래피(MC:Hex=1:1)로 정제하여 화합물 C 10 g (40 %)을 얻었다.25.4 g (122.95 mmol) of 2-bromonaphthalene was dissolved in 1000 mL of THF and slowly added n-buLi (114.7 mmol, 2.5M in hexane) at -78 ° C. After 30 minutes, the mixture was stirred at room temperature. After 30 minutes 14.1 g (40 mmol) of Compound B were added. After stirring for 12 hours, the mixture was extracted with distilled water and MC. The organic layer was dried over MgSO 4 , distilled under reduced pressure to remove the solvent, and purified by column chromatography (MC: Hex = 1: 1) to obtain Compound C 10 g (40%).

화합물 D의 제조Preparation of Compound D

화합물 C 10g (16.06 mmol)을 아세트산 500 mL에 가하고 130℃로 가열한 후 Zn 20.2 g을 천천히 첨가하였다. 그런 다음, HCl 20 mL를 천천히 가하였다. 30분후 Zn 10 g을 더 첨가하고 HCl 10 mL를 더 가하였다. 12시간 환류 교반 후 실온으로 냉각시켰다. 증류수를 넣고 생성된 고체를 감압 여과하였다. 얻어진 고체를 NaOH 수용액으로 씻어주고 컬럼크로마토그래피로 정제하여 화합물 D 6.5 g (11.04 mmol, 68.74 %)을 얻었다.10 g (16.06 mmol) of compound C were added to 500 mL of acetic acid and heated to 130 ° C., followed by the slow addition of 20.2 g of Zn. Then 20 mL of HCl was added slowly. After 30 minutes, 10 g of Zn was further added and 10 mL of HCl was further added. After stirring for 12 hours at reflux, the mixture was cooled to room temperature. Distilled water was added and the resulting solid was filtered under reduced pressure. The obtained solid was washed with an aqueous NaOH solution and purified by column chromatography to obtain 6.5 g (11.04 mmol, 68.74%) of Compound D.

화합물 68의 제조Preparation of Compound 68

화합물 D 5 g (8.49 mmol), 디페닐아민 3.7 g (22.09 mmol), Pd(OAc)2 0.09 g (0.42 mmol), NaOt-bu 3.26 g (33.99 mmol)을 넣고 질소하에서 톨루엔 200 mL과 P(t-bu)3 0.50 mL (1.019 mmol, 50% in xylene)을 넣고 환류 교반시켰다. 12시간 교반 후 실온으로 냉각하고, 증류수와 MC를 이용하여 추출하였다. 유기층을 MgSO4로 건조시킨 다음 감압증류하여 용매를 제거하고 컬럼크로마토그래피로 정제하여 화합물 68 2.9 g (75.8 %)을 얻었다.Compound D 5 g (8.49 mmol), diphenylamine 3.7 g (22.09 mmol), Pd (OAc) 2 0.09 g (0.42 mmol), NaOt-bu 3.26 g (33.99 mmol) were added and 200 mL of toluene and P ( t-bu) 3 0.50 mL (1.019 mmol, 50% in xylene) was added thereto, and the mixture was stirred under reflux. After stirring for 12 hours, the mixture was cooled to room temperature, and extracted with distilled water and MC. The organic layer was dried over MgSO 4 , distilled under reduced pressure to remove the solvent, and purified by column chromatography to obtain 2.9 g (75.8%) of the compound 68 .

1H NMR (CDCl3, 200MHz) : δ = 6.63(8H, m), 6.81(4H, m), 7.02(2H, m), 7.2(8H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.87~7.92(4H, m), 8(4H, m), 8.13(2H, m). MS/FAB : 764.96(found), 764.32(calculated). 1 H NMR (CDCl 3 , 200 MHz): δ = 6.63 (8H, m), 6.81 (4H, m), 7.02 (2H, m), 7.2 (8H, m), 7.58-7.59 (6H, m), 7.73 (2H, m), 7.87-7.92 (4H, m), 8 (4H, m), 8.13 (2H, m). MS / FAB: 764.96 (found), 764.32 (calculated).

상기 제조예 1의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 67을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to 67 were prepared using the method of Preparation Example 1, and the 1 H NMR and the MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.

[표 1]TABLE 1

Figure pat00041
Figure pat00041

Figure pat00042
Figure pat00042

Figure pat00043
Figure pat00043

Figure pat00044
Figure pat00044

[실시예 1-3] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 1-3 Fabrication of OLED Device Using 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 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 Ω / □) obtained from an OLED glass (manufactured by Samsung Corning Corporation) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol. It was used after. Next, the 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-TNATA) is installed in the cell in the vacuum deposition apparatus. After the evacuation and evacuation until the vacuum in the chamber reached 10 −6 torr, a current was applied 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 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.Then, to another cell of the vacuum vapor-deposit device N, N '-bis (α- naphthyl) - N, N' into the -diphenyl-4,4'-diamine (NPB) , and evaporation of the NPB by applying a current to the cell A 20 nm thick hole transport layer was deposited on the hole injection layer.

정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 하기 구조의 DNA(실시예 1 내지 3)를 넣고, 또 다른 셀에는 도판트로서 본 발명에 따른 화합물을 각각 넣은 후, 증착 속도를 100:3 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. DNA (Examples 1 to 3) having the following structure as a host was put into one cell in a vacuum deposition apparatus, and the compound according to the present invention was put into another cell as a dopant, and then the deposition rate was 100: 3. A 30 nm thick light emitting layer was deposited on the transfer layer.

Figure pat00045
Figure pat00045

이어서 전자전달층으로써 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 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) was deposited to a thickness of 20 nm as an electron transport layer, and lithium quinolate (Liq) was deposited to a thickness of 1 to 2 nm using an electron injection layer, followed by another vacuum. An OLED was manufactured by depositing an Al cathode to a thickness of 150 nm using a deposition equipment.

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.

상기 실시예 1 내지 3 에서 제조된 본 발명에 따른 유기 발광 화합물을 함유하는 OLED 소자의 발광 효율을 각각 1,000 cd/m2에서 측정하여 하기 표 2에 나타내었다.The luminous efficiency of the OLED device containing the organic light emitting compound according to the present invention prepared in Examples 1 to 3 was measured at 1,000 cd / m 2 , respectively, and is shown in Table 2 below.

[표 2]TABLE 2

Figure pat00046
Figure pat00046

상기 표 2에 나타난 바와 같이, 본 발명의 유기 발광 화합물들은 진한 청색을 구현할 수 있음을 알 수 있었다. 즉, 유기 발광 디스플레이에서 NTSC에 근접한 색을 구현하기 위하여 진한 청색이 필요할 때 본 발명의 유기 발광 화합물이 유용하게 쓰일 수 있다. 또한 페난트렌 유도체는 유리전이온도가 높아 열적 안정성이 뛰어난 장점이 있다. 이상에서와 같이 본 발명의 유기 발광 화합물은 고순도의 청색 발광 재료로 사용될 수 있음을 확인하였다. As shown in Table 2, it was found that the organic light emitting compounds of the present invention can implement a dark blue color. That is, the organic light emitting compound of the present invention may be usefully used when dark blue is required to realize a color close to NTSC in an organic light emitting display. In addition, the phenanthrene derivative has an advantage of excellent thermal stability due to its high glass transition temperature. As described above, it was confirmed that the organic light emitting compound of the present invention can be used as a high purity blue light emitting material.

Claims (10)

하기 화학식 1로 표시되는 유기 발광 화합물.
[화학식 1]
Figure pat00047

[상기 화학식 1에서,
Ar1 내지 Ar4는 서로 독립적으로 (C6-C30)아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 (C2-C30)헤테로아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 아다만틸, (C7-C30)바이사이클로알킬 또는
Figure pat00048
이거나, Ar1와 Ar2는 및 Ar3와 Ar4는 각각 방향족고리 또는 헤테로방향족고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 NR21, O, S 또는 SiR22R23으로 더 치환될 수 있고;
R1 내지 R6 및 R11 내지 R13은 각각 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)알콕시, (C6-C30)아릴옥시, 모노 또는 디(C1-C30)알킬아미노, 모노 또는 디(C6-C30)아릴아미노, (C6-C30)아릴(C1-C30)알킬아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이고;
R21 내지 R23은 서로 독립적으로 (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, 모폴리노, 티오모폴리노, 피페리디노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 아다만틸, 할로겐, 시아노, (C6-C30)아릴, (C2-C30)헤테로아릴, (C1-C30)트리알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이거나, R22와 R23은 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며;
상기 R1 내지 R6의 알킬기, 사이클로알킬기, 아릴, 헤테로아릴, 알콕시, 아릴옥시, 알킬아미노, 아릴아미노, 아릴알킬아미노, 트리알킬실릴, 디알킬아릴실릴 또는 트리아릴실릴; Ar1 내지 Ar4의 아릴, 헤테로아릴, 헤테로사이클로알킬, 사이클로알킬, 아다만틸 또는 바이사이클로알킬; Ar1와 Ar2가 Ar3와 Ar4가 각각 연결되어 형성된 융합고리; R21 내지 R23의 알킬, 할로알킬, 알콕시, 모폴리노, 티오모폴리노, 피페리디노, 헤테로시클로알킬, 시클로알킬, 아다만틸, 아릴, 헤테로아릴, 트리알킬실릴, 디알킬아릴실릴 또는 트리아릴실릴은 (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, (C1-C30)알킬티오, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 할로겐, 시아노, 나이트로, 하이드록시, (C6-C30)아릴, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C2-C30)헤테로아릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴로부터 선택되는 하나 이상의 치환기가 더 치환될 수 있다.]An organic light emitting compound represented by Formula 1 below.
[Formula 1]
Figure pat00047

[In the above formula (1)
Ar 1 to Ar 4 are each independently a 5 member comprising one or more selected from (C 2 -C 30) heteroaryl, N, O and S, including one or more selected from (C 6 -C 30) aryl, N, O and S To 7 membered heterocycloalkyl, (C3-C30) cycloalkyl, adamantyl, (C7-C30) bicycloalkyl or
Figure pat00048
Or Ar 1 and Ar 2 and Ar 3 and Ar 4 are each connected to (C3-C30) alkylene or (C3-C30) alkenylene with or without aromatic ring or heteroaromatic ring to form a fused ring. May be further substituted with NR 21 , O, S or SiR 22 R 23 ;
R 1 to R 6 and R 11 to R 13 are each independently hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C6-C30) aryl, (C2-C30) heteroaryl, (C1- C30) alkoxy, (C6-C30) aryloxy, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, (C6-C30) aryl (C1-C30) alkylamino, tri ( C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl;
R 21 to R 23 are independently of each other from (C 1 -C 30) alkyl, halo (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, morpholino, thiomorpholino, piperidino, N, O and S 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, adamantyl, halogen, cyano, (C6-C30) aryl, (C2-C30) heteroaryl, (C1) comprising one or more selected -C30) trialkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl, or R 22 and R 23 with or without fused ring (C3-C30) May be linked to alkylene or (C3-C30) alkenylene to form a fused ring;
The alkyl group, cycloalkyl group, aryl, heteroaryl, alkoxy, aryloxy, alkylamino, arylamino, arylalkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 1 to R 6 ; Aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar 1 to Ar 4 ; A fused ring formed by Ar 1 and Ar 2 connected to Ar 3 and Ar 4 , respectively; Alkyl, haloalkyl, alkoxy, morpholino, thiomorpholino, piperidino, heterocycloalkyl, cycloalkyl, adamantyl, aryl, heteroaryl, trialkylsilyl, dialkylarylsilyl of R 21 to R 23 Or triarylsilyl is (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C1-C30) alkylthio, piperidino, morpholino, thiomorpholino, N, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, halogen, cyano, nitro, hydroxy, (C6-C30) aryl, (C6-C30) comprising one or more selected from O and S ) Aryloxy, (C6-C30) arylthio, (C2-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, tri (C1- One or more substituents selected from C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl may be further substituted.] 제 1항에 있어서,
하기 화학식 2로 표시되는 유기 발광 화합물.
[화학식 2]
Figure pat00049

[상기 R5 및 R6은 각각 독립적으로 수소, (C6-C30)아릴 또는 (C2-C30)헤테로아릴이고;
Ar1 내지 Ar4는 서로 독립적으로 (C6-C30)아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 (C2-C30)헤테로아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 아다만틸, (C7-C30)바이사이클로알킬 또는
Figure pat00050
이거나, Ar1와 Ar2는 및 Ar3와 Ar4는 각각 방향족고리 또는 헤테로방향족고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 NR21, O, S 또는 SiR22R23으로 더 치환될 수 있고;
R21 내지 R23은 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이거나, R22와 R23은 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며;
상기 R5 및 R6의 아릴 또는 헤테로아릴; Ar1 내지 Ar4의 아릴, 헤테로아릴, 헤테로사이클로알킬, 사이클로알킬, 아다만틸 또는 바이사이클로알킬; Ar1와 Ar2가 Ar3와 Ar4가 각각 연결되어 형성된 융합고리; R21 내지 R23의 알킬 또는 아릴은 (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, (C1-C30)알킬티오, 피페리디노, 모폴리노, 티오모폴리노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 할로겐, 시아노, 나이트로, 하이드록시, (C6-C30)아릴, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C2-C30)헤테로아릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴로부터 선택되는 하나 이상의 치환기가 더 치환될 수 있다.]The method of claim 1,
An organic light emitting compound represented by Formula 2 below.
(2)
Figure pat00049

[Wherein R 5 and R 6 are each independently hydrogen, (C6-C30) aryl or (C2-C30) heteroaryl;
Ar 1 to Ar 4 are each independently a 5 member comprising one or more selected from (C 2 -C 30) heteroaryl, N, O and S, including one or more selected from (C 6 -C 30) aryl, N, O and S To 7 membered heterocycloalkyl, (C3-C30) cycloalkyl, adamantyl, (C7-C30) bicycloalkyl or
Figure pat00050
Or Ar 1 and Ar 2 and Ar 3 and Ar 4 are each connected to (C3-C30) alkylene or (C3-C30) alkenylene with or without aromatic ring or heteroaromatic ring to form a fused ring. May be further substituted with NR 21 , O, S or SiR 22 R 23 ;
R 21 to R 23 are independently of each other (C1-C30) alkyl or (C6-C30) aryl, or R 22 and R 23 are (C3-C30) alkylene or (C3-C30) with or without fused ring May be linked to alkenylene to form a fused ring;
Aryl or heteroaryl of R 5 and R 6 ; Aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar 1 to Ar 4 ; A fused ring formed by Ar 1 and Ar 2 connected to Ar 3 and Ar 4 , respectively; Alkyl or aryl of R 21 to R 23 is (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C1-C30) alkylthio, piperidino, morpholino, thiomo 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, halogen, cyano, nitro, hydroxy, (C6-C30) aryl containing one or more selected from polyno, N, O and S , (C6-C30) aryloxy, (C6-C30) arylthio, (C2-C30) heteroaryl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl One or more substituents selected from tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl may be further substituted.] 제 2항에 있어서,
상기
Figure pat00051
및
Figure pat00052
는 서로 독립적으로 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.
Figure pat00053

[R21 내지 R25은 서로 독립적으로 (C1-C60)알킬 또는 (C6-C60)아릴이다.]The method of claim 2,
remind
Figure pat00051
And
Figure pat00052
Are independently selected from the following structures:
Figure pat00053

[R 21 to R 25 are independently from each other (C1-C60) alkyl or (C6-C60) aryl.] 제 1항에 있어서,
하기 화합물로부터 선택되는 것을 특징으로 하는 유기 발광 화합물.
Figure pat00054

Figure pat00055

Figure pat00056

Figure pat00057

Figure pat00058

Figure pat00059

Figure pat00060

Figure pat00061

Figure pat00062

Figure pat00063

Figure pat00064

Figure pat00065

Figure pat00066

Figure pat00067

Figure pat00068

Figure pat00069

Figure pat00070

Figure pat00071

Figure pat00072
The method of claim 1,
An organic light emitting compound, which is selected from the following compounds.
Figure pat00054

Figure pat00055

Figure pat00056

Figure pat00057

Figure pat00058

Figure pat00059

Figure pat00060

Figure pat00061

Figure pat00062

Figure pat00063

Figure pat00064

Figure pat00065

Figure pat00066

Figure pat00067

Figure pat00068

Figure pat00069

Figure pat00070

Figure pat00071

Figure pat00072
 제 1항 내지 제4항에서 선택되는 어느 한 항에 따른 유기발광화합물을 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 4. 제 5항에 있어서,
상기 유기 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어져 있으며, 상기 유기물층은 상기 유기 발광 화합물 하나 이상과 하기 화학식 3 또는 화학식 4의 화합물에서 선택되는 호스트 하나 이상을 포함하는 것을 특징으로 하는 유기 발광 소자.
[화학식 3]
(Ar11)a-L1-(Ar12)b
[화학식 4]
(Ar13)c-L2-(Ar14)d
[상기 화학식 3 및 화학식 4에서,
L1는 (C6-C30)아릴렌 또는 (C4-C30)헤테로아릴렌이고;
L2는 안트라세닐렌이며;
Ar11 내지 Ar14은 서로 독립적으로 수소, 중수소, (C1-C30)알킬, (C1-C30)알콕시, 할로겐, (C4-C30)헤테로아릴, (C5-C30)시클로알킬 또는 (C6-C30)아릴이고, 상기 Ar11 내지 Ar14의 시클로알킬, 아릴 또는 헤테로아릴은 중수소, (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, (C3-C30)시클로알킬, 할로겐, 시아노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴로 이루어진 군으로부터 선택된 하나 이상이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 (C4-C30)헤테로아릴, 중수소, (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, (C3-C30)시클로알킬, 할로겐, 시아노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴로 이루어지는 군에서 선택되는 하나 이상의 치환기가 더 치환될 수 있고;
a, b, c 및 d는 서로 독립적으로 0 내지 4의 정수이다.]6. The method of claim 5,
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 compounds of Formula 3 or Formula 4 below. An organic light emitting element.
(3)
(Ar 11 ) a -L 1- (Ar 12 ) b
[Chemical Formula 4]
(Ar 13 ) c -L 2- (Ar 14 ) d
[In Formula 3 and Formula 4,
L 1 is (C6-C30) arylene or (C4-C30) heteroarylene;
L 2 is anthracenylene;
Ar 11 to Ar 14 are each independently hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, (C4-C30) heteroaryl, (C5-C30) cycloalkyl or (C6-C30) Aryl, and the cycloalkyl, aryl or heteroaryl of Ar 11 to Ar 14 is deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C3-C30) cycloalkyl, One or more selected from the group consisting of halogen, cyano, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl is unsubstituted or substituted (C6-C30) aryl or (C4-C30) heteroaryl, deuterium, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C3-C30) cycloalkyl, halogen, cyan At least one substituent selected from the group consisting of no, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl may be further substituted;
a, b, c and d are each independently an integer from 0 to 4.] 제 6항에 있어서,
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. The method of claim 6,
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 6항에 있어서,
상기 유기물층에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 발광 소자.The method of claim 6,
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 6항에 있어서,
상기 유기물층은 발광층 및 전하생성층을 포함하는 것을 특징으로 하는 유기 발광 소자.The method of claim 6,
The organic material layer is an organic light emitting device comprising a light emitting layer and a charge generating layer. 제 6항에 있어서,
한 쌍의 전극중 하나 이상의 내측표면에 환원성 도판트(dopant)와 유기물의 혼합 영역, 또는 산화성 도판트와 유기물의 혼합 영역이 배치되는 것을 특징으로 하는 유기 발광 소자.The method of claim 6,
An organic light emitting device according to claim 1, wherein a mixed region of a reducing dopant and an organic material or a mixed region of an oxidative dopant and an organic material is disposed on at least one inner surface of the pair of electrodes.
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