KR20110101444A - 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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KR20110101444A
KR20110101444A KR1020100020440A KR20100020440A KR20110101444A KR 20110101444 A KR20110101444 A KR 20110101444A KR 1020100020440 A KR1020100020440 A KR 1020100020440A KR 20100020440 A KR20100020440 A KR 20100020440A KR 20110101444 A KR20110101444 A KR 20110101444A
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light emitting
organic light
alkyl
compound
aryl
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김치식
조영준
권혁주
김봉옥
김성민
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다우어드밴스드디스플레이머티리얼 유한회사
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Priority to KR1020100020440A priority Critical patent/KR20110101444A/en
Priority to PCT/KR2011/001004 priority patent/WO2011111930A1/en
Priority to TW100107655A priority patent/TW201144407A/en
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Abstract

본 발명은 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 및 유기 태양전지에 관한 것으로, 상세하게는 본 발명에 따른 유기 발광 화합물은 하기 화학식 1 또는 2로 표시되는 것을 특징으로 한다.
[화학식 1]

Figure pat00054

[화학식 2]
Figure pat00055

상기 R1 내지 R5, X, Y, a, b, c 및 d는 발명의 상세한 설명에 기재된 바와 같다.
본 발명에 따른 유기 발광 화합물은 청색의 발광효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 양호한 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to a novel organic light emitting compound, an organic light emitting device and an organic solar cell including the same, and in detail, the organic light emitting compound according to the present invention is characterized by the following formula (1) or (2).
[Formula 1]
Figure pat00054

(2)
Figure pat00055

R 1 to R 5 , X, Y, a, b, c and d are as described in the detailed description of the invention.
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.

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 유기발광소자에 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 comprising 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 유기발광소자를 실현하기 위한 새로운 발광화합물을 발명하게 되었다. 본 발명의 목적은 상기한 문제점들을 해결하기 위하여 기존의 도판트 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기발광화합물 및 이를 발광재료로서 채용하는 고효율 및 장수명의 유기발광소자를 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 an excellent luminous efficiency and a greatly 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, excellent skeleton organic light emitting compound having a suitable color coordinate and high efficiency and long life organic light emitting device employing the same as the 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 1 또는 화학식 2로 표시되는 화합물로, 발광효율이 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 formula (1) or (2), the luminous efficiency is good and the color purity and life characteristics of the material There is an advantage that can produce an excellent OLED device excellent driving life.

[화학식 1][Formula 1]

Figure pat00002
Figure pat00002

[화학식 2][Formula 2]

Figure pat00003
Figure pat00003

[상기 R1 내지 R5는 서로 독립적으로 수소, (C1-C60)알킬, (C3-C60)시클로알킬, (C6-C60)아릴, N, O, S, P, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C2-60)헤테로아릴, (C1-60)알콕시, (C1-C60)알킬티오, (C6-60)아릴옥시, (C6-C60)아릴티오, (C6-30)아릴(C1-C30)알킬아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이고;[Wherein R 1 to R 5 are each independently selected from hydrogen, (C 1 -C 60) alkyl, (C 3 -C 60) cycloalkyl, (C 6 -C 60) aryl, N, O, S, P, Si and Se (C2-60) Heteroaryl, (C1-60) Alkoxy, (C1-C60) Alkylthio, (C6-60) Aryloxy, (C6-C60) Arylthio, (C6-30) Aryl (C1) -C30) alkylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl;

X는 화학결합이거나, -(CR6R7)m-, -N(R8)-, -Si(R9)(R10)-, -O-, -S-, -Se- 또는 (R11)C=C(R12)-이고;X is a chemical bond, or-(CR 6 R 7 ) m- , -N (R 8 )-, -Si (R 9 ) (R 10 )-, -O-, -S-, -Se- or (R 11 ) C = C (R 12 )-;

R6 내지 R12는 서로 독립적으로 수소, (C1-C60)알킬, (C3-C60)시클로알킬, (C6-C60)아릴, N, O, S, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C2-60)헤테로아릴, (C1-60)알콕시, (C1-C60)알킬티오, (C6-60)아릴옥시, (C6-C60)아릴티오, 모노 또는 디(C1-60)알킬아미노, 모노 또는 디(C6-60)아릴아미노, (C6-30)아릴(C1-C30)알킬아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이거나, R6과 R7, R9와 R10 및 R11와 R12는 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;R 6 to R 12 independently of one another include at least one selected from hydrogen, (C 1 -C 60 ) alkyl, (C 3 -C 60 ) cycloalkyl, (C 6 -C 60 ) aryl, N, O, S, Si and Se ( C2-60) heteroaryl, (C1-60) alkoxy, (C1-C60) alkylthio, (C6-60) aryloxy, (C6-C60) arylthio, mono or di (C1-60) alkylamino, mono Or di (C6-60) arylamino, (C6-30) aryl (C1-C30) alkylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri ( C 6 -C 30) arylsilyl or R 6 and R 7 , R 9 and R 10 and R 11 and R 12 are (C3-C60) alkylene or (C3-C60) alkenylene with or without fused ring Can be linked to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

Y는 (C6-C60)아릴렌, 아다만틸렌, N, O, S, P, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C3-C60)헤테로아릴렌,

Figure pat00004
또는
Figure pat00005
이고;Y is a (C3-C60) heteroarylene comprising at least one selected from (C6-C60) arylene, adamantylene, N, O, S, P, Si and Se,
Figure pat00004
or
Figure pat00005
ego;

Y1은 N, O, S, P, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C2-60)헤테로아릴렌이고;Y 1 is (C2-60) heteroarylene comprising one or more selected from N, O, S, P, Si and Se;

Z1 및 Z2는 서로 독립적으로 화학결합이거나, -(CR13R14)n-, -N(R15)-, -Si(R16)(R17)-, -O-, -S-, -Se- 또는 (R18)C=C(R19)-이고, 단 Z1 및 Z2는 동시에 화학결합이 아니고Z 1 and Z 2 are each independently a chemical bond or-(CR 13 R 14 ) n- , -N (R 15 )-, -Si (R 16 ) (R 17 )-, -O-, -S- , -Se- or (R 18 ) C = C (R 19 )-provided that Z 1 and Z 2 are not chemical bonds at the same time

R13 내지 R19는 서로 독립적으로 수소, (C1-C60)알킬, (C3-C60)시클로알킬, (C6-C60)아릴, N, O, S, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C2-60)헤테로아릴, (C1-60)알콕시, (C1-C60)알킬티오, (C6-60)아릴옥시, (C6-C60)아릴티오, 모노 또는 디(C1-60)알킬아미노, 모노 또는 디(C6-60)아릴아미노, (C6-30)아릴(C1-C30)알킬아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이거나, R13과 R14, R16와 R17 및 R18와 R19는 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;R 13 to R 19 independently of one another include at least one selected from hydrogen, (C 1 -C 60) alkyl, (C 3 -C 60) cycloalkyl, (C 6 -C 60) aryl, N, O, S, Si and Se ( C2-60) heteroaryl, (C1-60) alkoxy, (C1-C60) alkylthio, (C6-60) aryloxy, (C6-C60) arylthio, mono or di (C1-60) alkylamino, mono Or di (C6-60) arylamino, (C6-30) aryl (C1-C30) alkylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri ( C 6 -C 30) arylsilyl or R 13 and R 14 , R 16 and R 17 and R 18 and R 19 are (C3-C60) alkylene or (C3-C60) alkenylene with or without fused ring Can be linked to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

a, b 및 c는 서로 독립적으로 1 내지 4의 정수이고;a, b and c are each independently an integer from 1 to 4;

d는 1 내지 3의 정수이고; 및d is an integer of 1 to 3; And

m 및 n은 서로 독립적으로 1 내지 4의 정수이다.]
m and n are each independently an integer from 1 to 4.]

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 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. 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 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. 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-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. In addition, substituents containing the “(C 1 -C 60) 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. It may be. 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.

상기 Y는 1,2-페닐렌, 1,3-페닐렌, 1,4-페닐렌, 1,2-나프틸렌, 1,3-나프틸렌, 1,4-나프틸렌, 1,5-나프틸렌, 1,6-나프틸렌, 1,7-나프틸렌, 1,8-나프틸렌, 2,3-나프틸렌, 2,6-나프틸렌, 2,7-나프틸렌, 1,2-안트라세닐렌, 1,3-안트라세닐렌, 1,4-안트라세닐렌, 1,5-안트라세닐렌, 1,6-안트라세닐렌, 1,7-안트라세닐렌, 1,8-안트라세닐렌, 1,9-안트라세닐렌, 1,10-안트라세닐렌, 2,3-안트라세닐렌, 2,6-안트라세닐렌, 2,7안트라세닐렌, 2,9-안트라세닐렌, 2,10-안트라세닐렌, 9,10-안트라세닐렌, 4,2‘-비페닐렌, 4,3‘-비페닐렌, 4,4‘-비페닐렌, 1,2-트리페닐레닐렌, 1,3-트리페닐레닐렌, 1,4-트리페닐레닐렌, 1,6-트리페닐레닐렌, 1,7-트리페닐레닐렌, 1,8-트리페닐레닐렌, 1,10-트리페닐레닐렌, 1,11-트리페닐레닐렌, 1,12-트리페닐레닐렌, 2,3-트리페닐레닐렌, 2,6-트리페닐레닐렌, 2,7-트리페닐레닐렌, 2,11-트리페닐레닐렌, 1,2-플루오란테닐렌, 1,3-플루오란테닐렌, 1,4-플루오란테닐렌, 1,5-플루오란테닐렌, 1,6-플루오란테닐렌, 1,7-플루오란테닐렌, 1,8-플루오란테닐렌, 1,9-플루오란테닐렌, 1,10-플루오란테닐렌, 2,3-플루오란테닐렌, 2,4-플루오란테닐렌, 2,5-플루오란테닐렌, 2,7-플루오란테닐렌, 2,8-플루오란테닐렌, 2,9-플루오란테닐렌, 2,10-플루오란테닐렌, 3,4-플루오란테닐렌, 3,7-플루오란테닐렌, 3,8-플루오란테닐렌, 3,9-플루오란테닐렌, 3,10-플루오란테닐렌, 7,8-플루오란테닐렌, 7,9-플루오란테닐렌, 7,10-플루오란테닐렌, 8,9-플루오란테닐렌, 1,2-크리세닐렌, 1,3-크리세닐렌, 1,4-크리세닐렌, 1,5-크리세닐렌, 1,6-크리세닐렌, 1,7-크리세닐렌, 1,8-크리세닐렌, 1,9-크리세닐렌, 1,10-크리세닐렌, 1,11-크리세닐렌, 1,12-크리세닐렌, 2,3-크리세닐렌, 2,4-크리세닐렌, 2,5-크리세닐렌, 2,6-크리세닐렌, 2,8-크리세닐렌, 2,9-크리세닐렌, 2,10-크리세닐렌, 2,11-크리세닐렌, 2,12-크리세닐렌, 3,4-크리세닐렌, 3,5-크리세닐렌, 3,6-크리세닐렌, 3,9-크리세닐렌, 3,10-크리세닐렌, 3,11-크리세닐렌, 3,12-크리세닐렌, 4,5-크리세닐렌, 4,6-크리세닐렌, 4,11-크리세닐렌, 4,12-크리세닐렌, 5,6-크리세닐렌, 5,11-크리세닐렌, 5,12-크리세닐렌, 6,12-크리세닐렌, 4,4''-p-터페닐렌, 1,1'-비나프틸렌, 9,9'-비안트라세닐렌, 1,2-페난트릴렌, 1,3-페난트릴렌, 1,4-페난트릴렌, 1,5-페난트릴렌, 1,6-페난트릴렌, 1,7-페난트릴렌, 1,8-페난트릴렌, 1,9-페난트릴렌, 1,10-페난트릴렌, 2,3-페난트릴렌, 2,4-페난트릴렌, 2,5-페난트릴렌, 2,6-페난트릴렌, 2,7-페난트릴렌, 2,9-페난트릴렌, 2,10-페난트릴렌, 3,4-페난트릴렌, 3,5-페난트릴렌, 3,6-페난트릴렌, 3,9-페난트릴렌, 3,10-페난트릴렌, 4,5-페난트릴렌, 4,9-페난트릴렌, 4,10-페난트릴렌, 9,10-페난트릴렌, 1,2-피레닐렌, 1,3-피레닐렌, 1,4-피레닐렌, 1,5-피레닐렌, 1,6-피레닐렌, 1,7-피레닐렌, 1,8-피레닐렌, 1,9-피레닐렌, 1,10-피레닐렌, 2,4-피레닐렌, 2,5-피레닐렌, 2,7-피레닐렌, 4,5-피레닐렌, 4,9-피레닐렌, 4,10-피레닐렌, 1,2-퍼릴레닐렌, 1,3-퍼릴레닐렌, 1,4-퍼릴레닐렌, 1,5-퍼릴레닐렌, 1,6-퍼릴레닐렌, 1,7-퍼릴레닐렌, 1,8-퍼릴레닐렌, 1,9-퍼릴레닐렌, 1,10-퍼릴레닐렌, 1,11-퍼릴레닐렌, 1,12-퍼릴레닐렌, 2,3-퍼릴레닐렌, 2,4-퍼릴레닐렌, 2,5-퍼릴레닐렌, 2,8-퍼릴레닐렌, 2,9-퍼릴레닐렌, 2,10-퍼릴레닐렌, 2,11-퍼릴레닐렌, 3,4-퍼릴레닐렌, 3,9-퍼릴레닐렌 또는 3,10-퍼릴레닐렌, 2,2-아다만틸렌, 2,4-피리디닐렌, 3,4-피리디닐렌, 3,5-피리디닐렌, 2,6-피리디닐렌, 2,5-피리디닐렌, 2,3-피리디닐렌, 2,3-피라지닐렌, 2,5-피라지닐렌, 2,6-피라지닐렌, 2,4-트리아지닐렌, 2,3-퓨릴렌, 2,4-퓨릴렌, 2,5-퓨릴렌, 3,4-퓨릴렌, 2,3-티오펜일렌, 2,4-티오펜일렌, 2,5-티오펜일렌, 3,4-티오펜일렌, 2,3-셀레노페닐렌, 2,4-셀레노페닐렌, 2,5-셀레노페닐렌, 3,4-셀레노페닐렌, 2,5-(1,3,4-옥사디아졸)일렌, 2,5-(1,3,4-티아디아졸)일렌, 2,5-(1,3,4-셀레나디아졸)일렌, 2,3-퀴놀리닐렌, 2,4-퀴놀리닐렌, 2,5-퀴놀리닐렌, 2,6-퀴놀리닐렌, 2,7-퀴놀리닐렌, 2,8-퀴놀리닐렌, 3,4-퀴놀리닐렌, 3,5-퀴놀리닐렌, 3,6-퀴놀리닐렌, 3,7-퀴놀리닐렌, 3,8-퀴놀리닐렌, 4,5-퀴놀리닐렌, 4,6-퀴놀리닐렌, 4,7-퀴놀리닐렌, 4,8-퀴놀리닐렌, 5,6-퀴놀리닐렌, 5,7-퀴놀리닐렌, 5,8-퀴놀리닐렌, 6,7-퀴놀리닐렌, 6,8-퀴놀리닐렌, 7,8-퀴놀리닐렌, 2,3-퀴녹살리닐렌, 2,5-퀴녹살리닐렌, 2,6-퀴녹살리닐렌, 2,7-퀴녹살리닐렌, 2,8-퀴녹살리닐렌, 5,6-퀴녹살리닐렌, 5,7-퀴녹살리닐렌, 5,8-퀴녹살리닐렌, 6,7-퀴녹살리닐렌, 2,3-(티에노[3,4-b]피라진)일렌, 2,5-(티에노[3,4-b]피라진)일렌, 2,7-(티에노[3,4-b]피라진)일렌, 5,7-(티에노[3,4-b]피라진)일렌, 2,3-(셀레노페노[3,4-b]피라진)일렌, 2,5-(셀레노페노[3,4-b]피라진)일렌, 2,7-(셀레노페노[3,4-b]피라진)일렌, 5,7-(셀레노페노[3,4-b]피라진)일렌, 2,7-(벤조[d]티아졸)일렌, 2,6-(벤조[d]티아졸)일렌, 2,5-(벤조[d]티아졸)일렌, 2,4-(벤조[d]티아졸)일렌, 4,7-(벤조[d]티아졸)일렌, 5,7-(벤조[d]티아졸)일렌, 6,7-(벤조[d]티아졸)일렌, 5,6-(벤조[d]티아졸)일렌, 4,6-(벤조[d]티아졸)일렌, 4,5-(벤조[d]티아졸)일렌, 2,3-(1,10-페난트롤린)일렌, 2,4-(1,10-페난트롤린)일렌, 2,5-(1,10-페난트롤린)일렌, 2,6-(1,10-페난트롤린)일렌, 2,7-(1,10-페난트롤린)일렌, 2,8-(1,10-페난트롤린)일렌, 2,9-(1,10-페난트롤린)일렌, 3,4-(1,10-페난트롤린)일렌, 3,5-(1,10-페난트롤린)일렌, 3,6-(1,10-페난트롤린)일렌, 3,7-(1,10-페난트롤린)일렌, 3,8-(1,10-페난트롤린)일렌, 4,5-(1,10-페난트롤린)일렌, 4,6-(1,10-페난트롤린)일렌, 4,7-(1,10-페난트롤린)일렌, 5,6-(1,10-페난트롤린)일렌, 9,9-디메틸-1,2-플루오레닐렌, 9,9-디메틸-1,3-플루오레닐렌, 9,9-디메틸-1,4-플루오레닐렌, 9,9-디메틸-1,5-플루오레닐렌, 9,9-디메틸-1,6-플루오레닐렌, 9,9-디메틸-1,7-플루오레닐렌, 9,9-디메틸-1,8-플루오레닐렌, 9,9-디메틸-2,3-플루오레닐렌, 9,9-디메틸-2,4-플루오레닐렌, 9,9-디메틸-2,5-플루오레닐렌, 9,9-디메틸-2,6-플루오레닐렌, 9,9-디메틸-2,7-플루오레닐렌, 9,9-디메틸-3,4-플루오레닐렌, 9,9-디메틸-3,5-플루오레닐렌, 9,9-디메틸-3,6-플루오레닐렌, 9,9-디메틸-4,5-플루오레닐렌, 9,9-디에틸-1,2-플루오레닐렌, 9,9-디에틸-1,3-플루오레닐렌, 9,9-디에틸-1,4-플루오레닐렌, 9,9-디에틸-1,5-플루오레닐렌, 9,9-디에틸-1,6-플루오레닐렌, 9,9-디에틸-1,7-플루오레닐렌, 9,9-디에틸-1,8-플루오레닐렌, 9,9-디에틸-2,3-플루오레닐렌, 9,9-디에틸-2,4-플루오레닐렌, 9,9-디에틸-2,5-플루오레닐렌, 9,9-디에틸-2,6-플루오레닐렌, 9,9-디에틸-2,7-플루오레닐렌, 9,9-디에틸-3,4-플루오레닐렌, 9,9-디에틸-3,5-플루오레닐렌, 9,9-디에틸-3,6-플루오레닐렌, 9,9-디에틸-4,5-플루오레닐렌, 9,9-디페닐-1,2-플루오레닐렌, 9,9-디페닐-1,3-플루오레닐렌, 9,9-디페닐-1,4-플루오레닐렌, 9,9-디페닐-1,5-플루오레닐렌, 9,9-디페닐-1,6-플루오레닐렌, 9,9-디페닐-1,7-플루오레닐렌, 9,9-디페닐-1,8-플루오레닐렌, 9,9-디페닐-2,3-플루오레닐렌, 9,9-디페닐-2,4-플루오레닐렌, 9,9-디페닐-2,5-플루오레닐렌, 9,9-디페닐-2,6-플루오레닐렌, 9,9-디페닐-2,7-플루오레닐렌, 9,9-디페닐-3,4-플루오레닐렌, 9,9-디페닐-3,5-플루오레닐렌, 9,9-디페닐-3,6-플루오레닐렌, 9,9-디페닐-4,5-플루오레닐렌, 9,9-디시클로헥실-1,2-플루오레닐렌, 9,9-디시클로헥실-1,3-플루오레닐렌, 9,9-디시클로헥실-1,4-플루오레닐렌, 9,9-디시클로헥실-1,5-플루오레닐렌, 9,9-디시클로헥실-1,6-플루오레닐렌, 9,9-디시클로헥실-1,7-플루오레닐렌, 9,9-디시클로헥실-1,8-플루오레닐렌, 9,9-디시클로헥실-2,3-플루오레닐렌, 9,9-디시클로헥실-2,4-플루오레닐렌, 9,9-디시클로헥실-2,5-플루오레닐렌, 9,9-디시클로헥실-2,6-플루오레닐렌, 9,9-디시클로헥실-2,7-플루오레닐렌, 9,9-디시클로헥실-3,4-플루오레닐렌, 9,9-디시클로헥실-3,5-플루오레닐렌, 9,9-디시클로헥실-3,6-플루오레닐렌, 9,9-디시클로헥실-4,5-플루오레닐렌 또는 하기 구조에서 선택되는 2가기이나, 이에 한정되는 것은 아니다.Y is 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 1,5-naph Tylene, 1,6-naphthylene, 1,7-naphthylene, 1,8-naphthylene, 2,3-naphthylene, 2,6-naphthylene, 2,7-naphthylene, 1,2-anthracenyl Lene, 1,3-anthracenylene, 1,4-anthracenylene, 1,5-anthracenylene, 1,6-anthracenylene, 1,7-anthracenylene, 1,8-anthracenylene, 1,9-anthracenylene, 1,10-anthracenylene, 2,3-anthracenylene, 2,6-anthracenylene, 2,7 anthracenylene, 2,9-anthracenylene, 2,10 -Anthracenylene, 9,10-anthracenylene, 4,2'-biphenylene, 4,3'-biphenylene, 4,4'-biphenylene, 1,2-triphenylenylene, 1 , 3-triphenylenylene, 1,4-triphenylenylene, 1,6-triphenylenylene, 1,7-triphenylenylene, 1,8-triphenylenylene, 1,10-triphenyl Lenylene, 1,11-triphenylenylene, 1,12-triphenylenylene, 2,3-triphenylenylene, 2,6-triphenylenylene, 2,7-triphenylenylene, 2, 11-tree Phenylenylene, 1,2-fluoranthenylene, 1,3-fluoranthenylene, 1,4-fluoranthenylene, 1,5-fluoranthenylene, 1,6-fluoranthenylene, 1 , 7-fluoranthenylene, 1,8-fluoranthenylene, 1,9-fluoranthenylene, 1,10-fluoranthenylene, 2,3-fluoranthenylene, 2,4-fluorane Tenylene, 2,5-fluoranthenylene, 2,7-fluoranthenylene, 2,8-fluoranthenylene, 2,9-fluoranthenylene, 2,10-fluoranthenylene, 3, 4-Fluoranthenylene, 3,7-Fluoranthenylene, 3,8-Fluoranthenylene, 3,9-Fluorentenylene, 3,10-Fluorentenylene, 7,8-Fluorante Nylene, 7,9-Fluorentenylene, 7,10-Fluorentenylene, 8,9-Fluorentenylene, 1,2-Crisenylene, 1,3-Crisenylene, 1,4-Cri Cenylene, 1,5-Crisnylene, 1,6-Crisenylene, 1,7-Crissenylene, 1,8-Crissenylene, 1,9-Crissenylene, 1,10-Crissenylene , 1,11-crisenylene, 1,12-crisenylene, 2,3-crisenylene, 2,4-crisenylene, 2,5-crisenylene, 2,6-cre Risenylene, 2,8-crisenylene, 2,9-crisenylene, 2,10-crisenylene, 2,11-crisenylene, 2,12-crisenylene, 3,4-crisenyl Lene, 3,5-crisenylene, 3,6-crisenylene, 3,9-crisenylene, 3,10-crisenylene, 3,11-crisenylene, 3,12-crisenylene, 4,5-Crisnylene, 4,6-crisenylene, 4,11-crisenylene, 4,12-crisenylene, 5,6-crisenylene, 5,11-crisenylene, 5, 12-crisenylene, 6,12-crisenylene, 4,4 ''-p-terphenylene, 1,1'-vinaphthylene, 9,9'- bianthracenylene, 1,2-phenane Triylene, 1,3-phenanthryl, 1,4-phenanthryl, 1,5-phenanthryl, 1,6-phenanthryl, 1,7-phenanthryl, 1,8-phenanthryl , 1,9-phenanthryl, 1,10-phenanthryl, 2,3-phenanthryl, 2,4-phenanthryl, 2,5-phenanthryl, 2,6-phenanthryl, 2 , 7-phenanthryl, 2,9-phenanthryl, 2,10-phenanthryl, 3,4-phenanthryl, 3,5-phenanthryl, 3,6-phenanthryl, 3,9 Phenanthryl, 3,10-phenanthryl, 4,5-phenanthryl, 4,9-phenanthryl , 4,10-phenanthryl, 9,10-phenanthryl, 1,2-pyrenylene, 1,3-pyrenylene, 1,4-pyrenylene, 1,5-pyrenylene, 1,6-pyre Nylene, 1,7-pyrenylene, 1,8-pyrenylene, 1,9-pyrenylene, 1,10-pyrenylene, 2,4-pyrenylene, 2,5-pyrenylene, 2,7-pyrenylene , 4,5-pyrenylene, 4,9-pyrenylene, 4,10-pyrenylene, 1,2-perylenylene, 1,3-perylenylene, 1,4-perylenylene, 1,5- Perylenes, 1,6-perylenes, 1,7-perylenes, 1,8-perylenes, 1,9-perylenes, 1,10-perylenes, 1,11-perylenes Nylene, 1,12-peryleneylene, 2,3-peryleneylene, 2,4-peryleneylene, 2,5-peryleneylene, 2,8-peryleneylene, 2,9-peryleneylene, 2,10-perylenylene, 2,11-perylenylene, 3,4-perylenylene, 3,9-perylenylene or 3,10-perylenylene, 2,2-adamantylene, 2, 4-pyridinylene, 3,4-pyridinylene, 3,5-pyridinylene, 2,6-pyridinylene, 2,5-pyridinylene, 2,3-pyridinylene, 2,3- Pyrazinylene, 2,5-pyrazinylene, 2,6-pyrazinylene, 2,4-triage Ethylene, 2,3-furylene, 2,4-furylene, 2,5-furylene, 3,4-furylene, 2,3-thiophenylene, 2,4-thiophenylene, 2,5- Thiophenylene, 3,4-thiophenylene, 2,3-selenophenylene, 2,4-selenophenylene, 2,5-selenophenylene, 3,4-selenophenylene, 2, 5- (1,3,4-oxadiazole) ylene, 2,5- (1,3,4-thiadiazole) ylene, 2,5- (1,3,4-selenadiazole) ylene, 2 , 3-quinolinylene, 2,4-quinolinylene, 2,5-quinolinylene, 2,6-quinolinylene, 2,7-quinolinylene, 2,8-quinolinylene, 3,4 -Quinolinylene, 3,5-quinolinylene, 3,6-quinolinylene, 3,7-quinolinylene, 3,8-quinolinylene, 4,5-quinolinylene, 4,6-quine Nolinylene, 4,7-quinolinylene, 4,8-quinolinylene, 5,6-quinolinylene, 5,7-quinolinylene, 5,8-quinolinylene, 6,7-quinolinylene , 6,8-quinolinylene, 7,8-quinolinylene, 2,3-quinoxalinylene, 2,5-quinoxalinylene, 2,6-quinoxalinylene, 2,7-quinoxalinylene, 2 , 8-quinoxalinylene, 5,6-quinoxalinylene, 5,7-quinoxalinylene, 5,8-quinoxalinylene, 6,7-quinoxal Linylene, 2,3- (thieno [3,4-b] pyrazine) ylene, 2,5- (thieno [3,4-b] pyrazine) ylene, 2,7- (thieno [3,4 -b] pyrazine) ylene, 5,7- (thieno [3,4-b] pyrazine) ylene, 2,3- (selenopheno [3,4-b] pyrazine) ylene, 2,5- (sele Nofeno [3,4-b] pyrazine) ylene, 2,7- (selenopheno [3,4-b] pyrazine) ylene, 5,7- (selenopheno [3,4-b] pyrazine) ylene , 2,7- (benzo [d] thiazole) ylene, 2,6- (benzo [d] thiazole) ylene, 2,5- (benzo [d] thiazole) ylene, 2,4- (benzo [ d] thiazole) ylene, 4,7- (benzo [d] thiazole) ylene, 5,7- (benzo [d] thiazole) ylene, 6,7- (benzo [d] thiazole) ylene, 5 , 6- (benzo [d] thiazole) ylene, 4,6- (benzo [d] thiazole) ylene, 4,5- (benzo [d] thiazole) ylene, 2,3- (1,10- Phenanthroline) ylene, 2,4- (1,10-phenanthroline) ylene, 2,5- (1,10-phenanthroline) ylene, 2,6- (1,10-phenanthroline) ylene , 2,7- (1,10-phenanthroline) ylene, 2,8- (1,10-phenanthroline) ylene, 2,9- (1,10-phenanthroline) ylene, 3,4- (1,10-phenanthroline) ylene, 3,5- (1,10-phenanthroline) ylene, 3,6- (1,10-phenanthroline) Lene, 3,7- (1,10-phenanthroline) ylene, 3,8- (1,10-phenanthroline) ylene, 4,5- (1,10-phenanthroline) ylene, 4,6 -(1,10-phenanthroline) ylene, 4,7- (1,10-phenanthroline) ylene, 5,6- (1,10-phenanthroline) ylene, 9,9-dimethyl-1, 2-fluorenylene, 9,9-dimethyl-1,3-fluorenylene, 9,9-dimethyl-1,4-fluorenylene, 9,9-dimethyl-1,5-fluorenylene, 9, 9-dimethyl-1,6-fluorenylene, 9,9-dimethyl-1,7-fluorenylene, 9,9-dimethyl-1,8-fluorenylene, 9,9-dimethyl-2,3- Fluorenylene, 9,9-dimethyl-2,4-fluorenylene, 9,9-dimethyl-2,5-fluorenylene, 9,9-dimethyl-2,6-fluorenylene, 9,9- Dimethyl-2,7-fluorenylene, 9,9-dimethyl-3,4-fluorenylene, 9,9-dimethyl-3,5-fluorenylene, 9,9-dimethyl-3,6-fluore Nylene, 9,9-dimethyl-4,5-fluorenylene, 9,9-diethyl-1,2-fluorenylene, 9,9-diethyl-1,3-fluorenylene, 9,9- Diethyl-1,4-fluorenylene, 9,9-diethyl-1,5-fluorenylene, 9,9-diethyl-1,6-fluor Nylene, 9,9-diethyl-1,7-fluorenylene, 9,9-diethyl-1,8-fluorenylene, 9,9-diethyl-2,3-fluorenylene, 9,9 -Diethyl-2,4-fluorenylene, 9,9-diethyl-2,5-fluorenylene, 9,9-diethyl-2,6-fluorenylene, 9,9-diethyl-2 , 7-fluorenylene, 9,9-diethyl-3,4-fluorenylene, 9,9-diethyl-3,5-fluorenylene, 9,9-diethyl-3,6-fluore Nylene, 9,9-diethyl-4,5-fluorenylene, 9,9-diphenyl-1,2-fluorenylene, 9,9-diphenyl-1,3-fluorenylene, 9,9 -Diphenyl-1,4-fluorenylene, 9,9-diphenyl-1,5-fluorenylene, 9,9-diphenyl-1,6-fluorenylene, 9,9-diphenyl-1 , 7-fluorenylene, 9,9-diphenyl-1,8-fluorenylene, 9,9-diphenyl-2,3-fluorenylene, 9,9-diphenyl-2,4-fluore Nylene, 9,9-diphenyl-2,5-fluorenylene, 9,9-diphenyl-2,6-fluorenylene, 9,9-diphenyl-2,7-fluorenylene, 9,9 -Diphenyl-3,4-fluorenylene, 9,9-diphenyl-3,5-fluorenylene, 9,9-diphenyl-3,6-fluorenylene, 9,9 -Diphenyl-4,5-fluorenylene, 9,9-dicyclohexyl-1,2-fluorenylene, 9,9-dicyclohexyl-1,3-fluorenylene, 9,9-dicyclo Hexyl-1,4-fluorenylene, 9,9-dicyclohexyl-1,5-fluorenylene, 9,9-dicyclohexyl-1,6-fluorenylene, 9,9-dicyclohexyl- 1,7-fluorenylene, 9,9-dicyclohexyl-1,8-fluorenylene, 9,9-dicyclohexyl-2,3-fluorenylene, 9,9-dicyclohexyl-2, 4-fluorenylene, 9,9-dicyclohexyl-2,5-fluorenylene, 9,9-dicyclohexyl-2,6-fluorenylene, 9,9-dicyclohexyl-2,7- Fluorenylene, 9,9-dicyclohexyl-3,4-fluorenylene, 9,9-dicyclohexyl-3,5-fluorenylene, 9,9-dicyclohexyl-3,6-fluore Nylene, 9,9-dicyclohexyl-4,5-fluorenylene or a divalent group selected from the following structures, but is not limited thereto.

Figure pat00006
Figure pat00006

Figure pat00007
Figure pat00007

더욱 구체적으로, 상기 Y는 하기 구조에서 선택되는 2가기이다.More specifically, Y is a divalent group selected from the following structures.

Figure pat00008
Figure pat00008

Figure pat00009
Figure pat00009

상기

Figure pat00010
또는
Figure pat00011
는 하기 구조에서 선택되나, 이에 한정되는 것은 아니다.remind
Figure pat00010
or
Figure pat00011
Is selected from the following structures, but is not limited thereto.

Figure pat00012
Figure pat00012

더욱 구체적으로, 상기

Figure pat00013
또는
Figure pat00014
는 하기 구조에서 선택된다.More specifically, the
Figure pat00013
or
Figure pat00014
Is selected from the following structures.

Figure pat00015
Figure pat00015

발명에 따른 유기 발광 화합물은 예를 들어 하기 반응식 1 내지 4에 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 Schemes 1 to 4 below, but is not limited to the following scheme.

[반응식 1]Scheme 1

Figure pat00016
Figure pat00016

[반응식 2]Scheme 2

Figure pat00017
Figure pat00017

[반응식 3]Scheme 3

Figure pat00018
Figure pat00018

[반응식 4]Scheme 4

Figure pat00019
Figure pat00019

(상기 반응식 1 내지 4에서 R1 내지 R5, X, Y, a, b, c 및 d는 상기 화학식 1 및 2에서 정의한 바와 동일하다.)(In Reaction Schemes 1 to 4, R 1 to R 5 , X, Y, a, b, c and d are the same as defined in Chemical Formulas 1 and 2 above.)

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 1 또는 2의 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 Formula 1 or 2 above.

본 발명에 따른 유기 발광 소자는 상기 유기물층이 발광층을 포함하며, 상기 발광층은 상기 화학식 1 또는 2의 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.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 or 2 as a light emitting dopant, and the organic material of the present invention. The host applied to the light emitting device is not particularly limited, but is preferably selected from compounds represented by the following Chemical Formula 3 or Chemical Formula 4.

[화학식 3](3)

(Ar1)e-L1-(Ar2)f (Ar 1 ) e -L 1- (Ar 2 ) f

[화학식 4][Formula 4]

(Ar3)g-L2-(Ar4)h (Ar 3 ) g -L 2- (Ar 4 ) h

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

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

L2는 안트라세닐렌이며;L 2 is anthracenylene;

Ar1 내지 Ar4은 서로 독립적으로 수소 또는 중수소이거나, (C1-C60)알킬, (C1-C60)알콕시, 할로겐, (C4-C60)헤테로아릴, (C5-C60)시클로알킬 또는 (C6-C60)아릴로부터 선택되고, 상기 Ar1 내지 Ar4의 시클로알킬, 아릴 또는 헤테로아릴은 할로겐이 치환되거나 치환되지 않은 (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 않은 (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 1 to Ar 4 are independently of each other hydrogen or deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) Is selected from aryl, and the cycloalkyl, aryl or heteroaryl of Ar 1 to Ar 4 is substituted or unsubstituted (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, substituted or unsubstituted halogen, (C1-C60) alkyl, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri One or more substituents selected from the group consisting of (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted;

e, f, g 및 h는 독립적으로 0 내지 4의 정수이다.]
e, f, g and h are independently integers from 0 to 4.

상기 화학식 3 및 화학식 4의 호스트는 화학식 5 내지 화학식 7로 화합물로 예시될 수 있다.The host of Formula 3 and Formula 4 may be exemplified as a compound of Formula 5 to Formula 7.

[화학식 5][Chemical Formula 5]

Figure pat00020
Figure pat00020

[화학식 6][Formula 6]

Figure pat00021
Figure pat00021

[화학식 7][Formula 7]

Figure pat00022
Figure pat00022

[상기 화학식 5 내지 화학식 7에서, [In Formula 5 to Formula 7,

R21 및 R22는 서로 독립적으로 수소, 중수소, (C1-C60)알킬, 할로겐, (C6-C60)아릴, (C4-C60)헤테로아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬 또는 (C3-C60)시클로알킬이며, 상기 R21 및 R22의 아릴 또는 헤테로아릴은 (C1-C60)알킬, 할로(C1-C60)알킬, (C1-C60)알콕시, (C3-C60)시클로알킬, (C6-C60)아릴, (C4-C60)헤테로아릴, 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 있으며;R 21 and R 22 independently of one another include at least one selected from hydrogen, deuterium, (C1-C60) alkyl, halogen, (C6-C60) aryl, (C4-C60) heteroaryl, N, O and S Heterocycloalkyl or (C3-C60) cycloalkyl of 1 to 6 members, wherein the aryl or heteroaryl of R 21 and R 22 is (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) Alkoxy, (C3-C60) cycloalkyl, (C6-C60) aryl, (C4-C60) heteroaryl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) One or more substituents selected from the group consisting of arylsilyl or tri (C6-C60) arylsilyl may be further substituted;

R23 내지 R26는 서로 독립적으로 수소, 중수소, (C1-C60)알킬, (C1-C60)알콕시, 할로겐, (C4-C60)헤테로아릴, (C5-C60)시클로알킬 또는 (C6-C60)아릴이며, 상기 R103 내지 R106의 헤테로아릴, 시클로알킬 또는 아릴은 할로겐이 치환되거나 치환되지 않은 (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;R 23 to R 26 independently of one another are hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) Aryl, and the heteroaryl, cycloalkyl or aryl of R 103 to R 106 is (C 1 -C 60) alkyl, (C 1 -C 60) alkoxy, (C 3 -C 60) cycloalkyl, halogen substituted or unsubstituted. 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;

L11 및 L13는 서로 독립적으로 화합결합이거나 (C1-C60)알킬, (C1-C60)알콕시, (C6-C60)아릴, (C4-C60)헤테로아릴 또는 할로겐으로부터 선택된 하나 이상이 치환되거나 치환되지 않은 (C6-C60)아릴렌이며, ;L 11 and L 13 are each independently a compound bond or substituted or substituted with one or more selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl or halogen Unsubstituted (C6-C60) arylene;

Ar11 및 Ar12는 하기 구조에서 선택되는 아릴 또는 (C4-C60)헤테로아릴이며, Ar 11 and Ar 12 are aryl or (C4-C60) heteroaryl selected from the following structures,

Figure pat00023
Figure pat00023

상기 Ar11 및 Ar12의 아릴 또는 헤테로아릴은 (C1-C60)알킬, (C1-C60)알콕시, (C6-C60)아릴 또는 (C4-C60)헤테로아릴로부터 선택된 치환기가 하나이상 치환될 수 있고;The aryl or heteroaryl of Ar 11 and Ar 12 may be substituted with one or more substituents selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl or (C4-C60) heteroaryl. ;

L12는 (C6-C60)아릴렌, (C4-C60)헤테로아릴렌 또는

Figure pat00024
이며, 상기 L12의 아릴렌 또는 헤테로아릴렌은 (C1-C60)알킬, (C1-C60)알콕시, (C6-C60)아릴, (C4-C60)헤테로아릴 또는 할로겐으로부터 선택된 하나 이상이 치환될 수 있으며;L 12 is (C6-C60) arylene, (C4-C60) heteroarylene or
Figure pat00024
Wherein the arylene or heteroarylene of L 12 may be substituted with one or more selected from (C 1 -C 60) alkyl, (C 1 -C 60) alkoxy, (C 6 -C 60) aryl, (C 4 -C 60) heteroaryl or halogen Can be;

R31 내지 R34는 서로 독립적으로 수소, 중수소, (C1-C60)알킬 또는 (C6-C60)아릴이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며,R 31 to R 34 independently of one another are hydrogen, deuterium, (C1-C60) alkyl or (C6-C60) aryl, or (C3-C60) alkylene or (C3-with or without fused ring with adjacent substituents) C60) may be linked to alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring,

R35 내지 R38는 서로 독립적으로 수소, 중수소, (C1-C60)알킬, (C1-C60)알콕시, (C6-C60)아릴, (C4-C60)헤테로아릴 또는 할로겐이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있다.]
R 35 to R 38 are independently of each other hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl or halogen, or a fused ring with adjacent substituents May be linked to (C3-C60) alkylene or (C3-C60) alkenylene, with or without an alicyclic ring and a monocyclic or polycyclic aromatic ring.]

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 내지 화학식 7로부터 선택되는 화합물을 발광 호스트로 채택하는 경우, 본 발명의 화학식 1 또는 2의 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 Formula 3 to Formula 7 is adopted as a light emitting host, it can be described that it plays a role to substantially compensate for the electrical shortcomings of the organic light emitting compound of Formula 1 or 2 of the present invention.

본 발명의 유기 발광 소자에 있어서, 화학식 1 또는 2의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있으며, 아릴아민계 화합물 또는 스티릴아릴아민계 화합물의 예로 하기의 화학식 8의 화합물이 있으나, 이에 한정되는 것을 아니다.In the organic light emitting device of the present invention, an organic light emitting compound of Formula 1 or 2, 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 Examples of the compound or styrylarylamine-based compound include, but are not limited to, the compound of Formula 8 below.

[화학식 8][Formula 8]

Figure pat00025
Figure pat00025

[상기 화학식 8에서, Ar31 및 Ar32는 서로 독립적으로 (C1-C60)알킬, (C6-C60)아릴, (C4-C60)헤테로아릴, (C6-C60)아릴아미노, (C1-C60)알킬아미노, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬 또는 (C3-C60)시클로알킬이고, Ar31 및 Ar32는 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하고; [In Formula 8, Ar 31 and Ar 32 are independently of each other (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, (C6-C60) arylamino, (C1-C60) 5- to 6-membered heterocycloalkyl or (C3-C60) cycloalkyl comprising at least one selected from alkylamino, N, O and S, and Ar 31 and Ar 32 may or may not contain fused rings (C3 -C60) alkylene or (C3-C60) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

k가 1인 경우 Ar33은 (C6-C60)아릴 또는 (C4-C60)헤테로아릴 또는 하기 구조의 치환기이고;when k is 1 Ar 33 is (C6-C60) aryl or (C4-C60) heteroaryl or a substituent of the following structure;

Figure pat00026
Figure pat00026

k가 2인 경우 Ar33는 (C6-C60)아릴렌, (C4-C60)헤테로아릴렌 또는 하기 구조의 치환기이고;when k is 2, Ar 33 is (C6-C60) arylene, (C4-C60) heteroarylene or a substituent of the following structure;

Figure pat00027
Figure pat00027

Ar34 및 Ar35은 서로 독립적으로 (C6-C60)아릴렌 또는 (C4-C60)헤테로아릴렌이고;Ar 34 and Ar 35 independently of one another are (C6-C60) arylene or (C4-C60) heteroarylene;

R91 내지 R93는 서로 독립적으로 수소, (C1-C60)알킬 또는 (C6-C60)아릴이고;R 91 to R 93 are independently of each other hydrogen, (C1-C60) alkyl or (C6-C60) aryl;

p는 1 내지 4의 정수이며, q는 0 또는 1의 정수이고,p is an integer of 1 to 4, q is an integer of 0 or 1,

상기 Ar31 및 Ar32의 알킬, 아릴, 헤테로아릴, 아릴아미노, 알킬아미노, 시클로알킬 또는 헤테로시클로알킬, 또는 상기 Ar33의 아릴, 헤테로아릴, 아릴렌 또는 헤테로아릴렌, 또는 상기 Ar34 및 Ar35의 아릴렌 및 헤테로아릴렌, 또는 R191 내지 R193의 알킬 또는 아릴은 할로겐, (C1-C60)알킬, (C6-C60)아릴, (C4-C60)헤테로아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C3-C60)시클로알킬, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴, 트리(C6-C60)아릴실릴, 아다만틸, (C7-C60)바이시클로알킬, (C2-C60)알케닐, (C2-C60)알키닐, 시아노, (C1-C60)알킬아미노, (C6-C60)아릴아미노, (C6-C60)아르(C1-C60)알킬, (C6-C60)아릴옥시, (C1-C60)알킬옥시, (C6-C60)아릴티오, (C1-C60)알킬티오, (C1-C60)알콕시카보닐, (C1-C60)알킬카보닐, (C6-C60)아릴카보닐, 카르복실, 나이트로, 하이드록시로 이루어진 군에서 선택되는 하나 이상의 치환기가 더 치환될 수 있다.]Alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl of Ar 31 and Ar 32 , or aryl, heteroaryl, arylene or heteroarylene of Ar 33 , or Ar 34 and Ar Arylene and heteroarylene of 35 , or alkyl or aryl of R 191 to R 193 are selected from halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, N, O and S 5- to 6-membered heterocycloalkyl, at least one selected from (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri ( C6-C60) arylsilyl, adamantyl, (C7-C60) bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, (C1-C60) alkylamino, (C6- C60) arylamino, (C6-C60) ar (C1-C60) alkyl, (C6-C60) aryloxy, (C1-C60) alkyloxy, (C6-C60) arylthio, (C1-C60) alkylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, The bytes, one or more substituents selected from the group consisting of hydroxy may further be substituted.]

상기 아릴아민계 화합물 또는 스티릴아릴아민계 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있으나, 하기 화합물로 한정되는 것은 아니다.The arylamine-based compound or styrylarylamine-based compound may be more specifically exemplified as the following compound, but is not limited thereto.

Figure pat00028
Figure pat00028

또한, 본 발명의 유기 발광 소자에 있어서, 유기물층에 상기 화학식 1 또는 2의 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 addition to the organic light emitting compound of Chemical Formula 1 or 2, the organic material layer is composed of Group 1, 2, 4, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element. One or more metals selected from the group may be further included, and the organic material layer may include a light emitting layer and a charge generating layer.

본 발명의 화학식 1 또는 2의 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 전기 발광 소자를 구현할 수도 있다.An organic light emitting device including the organic light emitting compound of Formula 1 or 2 of the present invention is a subpixel, and includes Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au And an organic electroluminescent 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 Ag is simultaneously patterned in parallel.

또한, 상기 유기물층에 상기 유기 발광 화합물 이외에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 발광 소자를 형성할 수 있다.In addition, an organic light emitting device that emits white light may be formed in the organic material layer by simultaneously including one or more organic light emitting layers emitting blue, red, or green light in addition to the organic light emitting compound.

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 전기 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 electroluminescent device of the present invention, it is also possible to arrange a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidative dopant on at least one surface of a pair of electrodes thus produced. desirable. 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.

[제조예 1]화합물 91의 제조Preparation Example 1 Preparation of Compound 91

Figure pat00029
Figure pat00029

화합물 A의 제조Preparation of Compound A

4-브로모비페닐 30g(0.12mol)를 1구(one-neck) 플라스크에 넣고 진공 분위기로 만들고 아르곤으로 충전하였다. THF 500ml를 넣고 -78℃에서 10분 간 교반하였다. n-BuLi(2.5M in hexane) 77ml(0.19mol)를 적가하고 1시간 30분간 -78℃에서 교반하였다. 트리메틸보레이트 21.9ml(0.19mol)를 -78℃에서 첨가하였다. 30분간 -78℃에서 교반한 후 실온에서 4시간 동안 교반하였다. 반응이 종결되면 증류수와 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조 시킨 후 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 A 21g(84%)를 분리하였다.30 g (0.12 mol) of 4-bromobiphenyl was placed in a one-necked flask, vacuumed and filled with argon. 500 ml of THF was added and stirred at -78 ° C for 10 minutes. 77 ml (0.19 mol) of n-BuLi (2.5 M in hexane) was added dropwise and stirred at −78 ° C. for 1 hour 30 minutes. 21.9 ml (0.19 mol) of trimethylborate was added at -78 ° C. Stirred at −78 ° C. for 30 minutes and then stirred at room temperature for 4 hours. After the reaction was completed, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO 4 , and then the solvent was removed using a rotary evaporator, and 21 g (84%) of pure product A was isolated by column chromatography using hexane and EA as developing solvents.

화합물 B의 제조Preparation of Compound B

1-브로모-4-아이오도벤젠 29g(0.10mol)과 화합물 A 21g(0.10mol) 와 테트라키스(트리페닐포스핀)팔라듐(Tetrakis(triphenylphosphine)Palladium) 5.9g(5.1mmol)를 2구(Two-neck) 플라스크에 첨가하였다. 톨루엔을 첨가하면서 교반을 시키고 2M의 K2CO3 265ml(0.5mol)과 에탄올 265ml를 첨가한 후, 100℃에서 5시간동안 환류시켰다. 반응이 종결되면 실온으로 냉각시킨 후 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 B 23g(74%)를 분리하였다.29 g (0.10 mol) of 1-bromo-4-iodobenzene, 21 g (0.10 mol) of Compound A and 5.9 g (5.1 mmol) of Tetrakis (triphenylphosphine) Palladium Two-neck flask was added. The mixture was stirred with the addition of toluene and 265 ml (0.5 mol) of 2M K 2 CO 3 and 265 ml of ethanol were added, followed by refluxing at 100 ° C. for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and 23 g (74%) of pure product B was separated by column chromatography using hexane and EA as developing solvents.

화합물 C의 제조Preparation of Compound C

화합물 B 2g(0.074mol)을 1구(one-neck) 플라스크에 넣고 질소 상태를 만들었다. THF을 첨가한 후 -78℃ 로 온도를 유지한 상태에서 10분간 교반하였다. n-부틸리튬(2.5M in hexane) 44.6ml(0.11mol)를 적가한 후 1시간 동안 -78℃에서 교반하였다. 그 후 DMF 8.1ml(0.11mmol)를 첨가하고 10분 동안 교반한 후 실온에서 4시간 동안 교반하였다. 반응이 종결된 다음 HCl 2.5mL 첨가한 후 실온으로 만든 후 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 C 19g(89%)를 분리하였다.2 g (0.074 mol) of Compound B was placed in a one-neck flask to make nitrogen. After adding THF, it stirred for 10 minutes, maintaining temperature at -78 degreeC. 44.6 ml (0.11 mol) of n-butyllithium (2.5M in hexane) was added dropwise and stirred at -78 ° C for 1 hour. Then 8.1 ml (0.11 mmol) of DMF were added and stirred for 10 minutes, followed by stirring at room temperature for 4 hours. After completion of the reaction, 2.5 mL of HCl was added thereto, and the mixture was brought to room temperature, and extracted with distilled water and EA. The organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and 19 g (89%) of pure product C was isolated by column chromatography using hexane and EA as developing solvents.

화합물 D의 제조Preparation of Compound D

9H-플루오렌 60g(0.36mol)를 1구(one-neck) 플라스크에 넣고 진공 분위기로 만들고 아르곤으로 충전하였다. 프로필렌카보네이트(Propylene carbonate) 500ml를 넣고 60℃에서 9H-플루오렌이 녹을 때 까지 교반하였다. NBS 64g(0.36mol)를 첨가하고 60℃에서 1시간 동안 교반하였다. 반응이 종결되면 증류수를 넣고 여과 한 후 얻은 고체를 EA로 녹여서 증류수를 넣고 추출하였. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 에탄올로 재결정 작업으로 순수한 생성물 D 64g(73%)을 얻었다.60 g (0.36 mol) of 9H-fluorene was placed in a one-necked flask, vacuumed and filled with argon. 500 ml of propylene carbonate was added and stirred at 60 ° C. until 9H-fluorene was dissolved. 64 g (0.36 mol) of NBS were added and stirred at 60 ° C. for 1 hour. After the reaction was completed, distilled water was added, filtered, and the obtained solid was dissolved in EA, followed by distilled water, and extracted. The organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and recrystallized with ethanol to obtain 64 g (73%) of pure product D.

화합물 E의 제조Preparation of Compound E

화합물 D 40g(0.16mol)과 아이오딘(Iodine) 16.9g(0.066mol), 요오드산 6.89g(0.039mol)를 2구(two-neck) 플라스크에 넣고 증류수 30ml와 아세트산 600mL, 황산 14.4mL를 넣고 85℃에서 4시간 동안 교반하였다. 반응이 종결된 다음 실온으로 완전히 식은 후 아세트산과 증류수로 씻어주고 여과하여 순수한 생성물 E 49g(82%)을 얻었다.40 g (0.16 mol) of compound D , 16.9 g (0.066 mol) of iodine, 6.89 g (0.039 mol) of iodine acid were placed in a two-neck flask, and 30 ml of distilled water, 600 mL of acetic acid, and 14.4 mL of sulfuric acid were added. Stir at 85 ° C. for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, washed with acetic acid and distilled water, and filtered to obtain 49 g (82%) of pure product E.

화합물 F의 제조Preparation of Compound F

화합물 E 49g(0.13mol)과 KOH 33g(0.60mol), KI 2.2g(0.013mol)를 1구(one-neck) 플라스크에 넣고 진공 분위기로 만들고 아르곤으로 충전하였다. DMSO(anhydrous) 500ml를 넣고 0℃에서 10분 간 교반하였다. 브로모에탄 23mL(0.30mol)를 적가하고 30분간 -10℃에서 교반한 다음, 실온에서 9시간 동안 교반하였다. 반응이 종결되면 증류수를 과량 넣어서 생성된 고체를 여과한 후, 얻은 고체를 MC로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산을 전개 용매로 하여 컬럼크로마토그래피로순수한 생성물 F 37g(66%)을 분리하였다.49 g (0.13 mol) of Compound E, 33 g (0.60 mol) of KOH, and 2.2 g (0.013 mol) of KI were placed in a one-neck flask and vacuum-filled with argon. 500 ml of DMSO (anhydrous) was added thereto and stirred at 0 ° C. for 10 minutes. 23 mL (0.30 mol) of bromoethane was added dropwise and stirred at −10 ° C. for 30 minutes, followed by stirring at room temperature for 9 hours. After the reaction was completed, the resulting solid was filtered with excess distilled water, and the obtained solid was extracted with MC. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator, and 37 g (66%) of pure product F was purified by column chromatography using hexane as a developing solvent.

화합물 G의 제조Preparation of Compound G

화합물 F 30g(0.07mol)과 카바졸 15.2g(0.09mol), 구리(Cpper) 2.5g(0.03mol)과 18-크라운-6 1.4g(0.005mol), K2CO3 38.8g(0.28mol)를 2구(two-neck) 플라스크에 넣고 진공 분위기로 만들고 아르곤으로 충전하였다. 1,2-디클로로벤젠 250ml를 넣고 180℃에서 6시간 동안 환류시키며 교반하였다. 반응이 종결된 다음 셀라이트 필터를 사용하여 구리를 제거하고 MC로 녹인 후 용매를 제거한 후 디클로로메탄과 헥산을 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 G 23g(76%)을 분리하였다.30 g (0.07 mol) of compound F , 15.2 g (0.09 mol) of carbazole, 2.5 g (0.03 mol) of copper (Cpper), 1.4 g (0.005 mol) of 18-crown-6, 38.8 g (0.28 mol) of K2CO3 The two-neck flask was placed in a vacuum atmosphere and filled with argon. 250 ml of 1,2-dichlorobenzene was added thereto, and the mixture was stirred under reflux at 180 ° C. for 6 hours. After completion of the reaction, copper was removed using a Celite filter, dissolved in MC, and the solvent was removed. Then, 23 g (76%) of pure product G was separated by column chromatography using dichloromethane and hexane as a developing solvent.

화합물 H의 제조Preparation of Compound H

화합물 G 20g(0.042mol)을 1구(one-neck) 플라스크에 넣고 질소 분위기로 만들었다. THF를 첨가한 후 -78℃ 로 온도를 유지한 상태에서 10분간 교반하였다. n-부틸리튬(2.5M in hexane) 40ml(0.063mol)를 적가한 후 1시간 동안 -78℃에서 교반하였다. 그 후 DMF 4.8ml(0.063mmol)를 첨가하고 10분 동안 교반한 후 실온에서 4시간 동안 교반하였다. 반응이 종결되면 HCl 2.5mL 첨가한 후 실온으로 만들고 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 H 13g(72%)를 분리하였다.20 g (0.042 mol) of compound G was placed in a one-necked flask and placed in a nitrogen atmosphere. After adding THF, it stirred for 10 minutes, maintaining temperature at -78 degreeC. 40 ml (0.063 mol) of n-butyllithium (2.5M in hexane) was added dropwise, followed by stirring at −78 ° C. for 1 hour. Then 4.8 ml (0.063 mmol) of DMF were added and stirred for 10 minutes, followed by stirring at room temperature for 4 hours. After the reaction was completed, 2.5 mL of HCl was added, and the mixture was brought to room temperature, and extracted with distilled water and EA. The organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and 13 g (72%) of pure product H was isolated by column chromatography using hexane and EA as developing solvents.

화합물 I의 제조Preparation of Compound I

화합물 H 13g(0.031mol)과 트리에틸포스파이트 10mL(0.062mol)을 1구(one-neck) 플라스크에 첨가하였다. 0℃에서 아이오딘 7.9g(0.031mol)넣고 30분간 교반한 다음, 실온에서 12시간 교반시켰다. 반응이 종결된 후 진공 승화장치로 포스파이트 를 제거하고 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 I 16g(87%)을 분리하였다.13 g (0.031 mol) of compound H and 10 mL (0.062 mol) of triethylphosphite were added to a one-neck flask. 7.9 g (0.031 mol) of iodine was added at 0 ° C. and stirred for 30 minutes, followed by stirring at room temperature for 12 hours. After the reaction was completed, the phosphite was removed by a vacuum sublimation apparatus, and extracted with distilled water and EA. The organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and 16 g (87%) of pure product I was isolated by column chromatography using hexane and EA as developing solvents.

화합물 91의 제조Preparation of Compound 91

화합물 I 16g(0.029mol)과 화합물 C 7.6g(0.029mol)을 1구(one-neck) 플라스크에 넣은 후 진공으로 만든 다음 아르곤 분위기로 만들었다. THF 600mL를 첨가한 후 0℃에서 10분간 교반하고, 포타슘 tert-부톡사이드 35.7mL(0.035mol)를 천천히 첨가하였다. 0℃에서 10분간 교반하고, 실온에서 3시간동안 교반시켰다. 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물인 화합물 91 17g(89%)을 분리하였다.16 g (0.029 mol) of Compound I and 7.6 g (0.029 mol) of Compound C were placed in a one-neck flask, vacuumed, and then placed in an argon atmosphere. After adding 600 mL of THF, the mixture was stirred for 10 minutes at 0 ° C., and 35.7 mL (0.035 mol) of potassium tert-butoxide was added slowly. Stirred at 0 ° C. for 10 minutes and at room temperature for 3 hours. Extracted with distilled water and EA. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Then, 17 g (89%) of Compound 91 , a pure product, was separated by column chromatography using hexane and EA as developing solvents.

1H NMR(CDCl3, 200 MHz): δ = 0.9(6H, m), 1.91(4H, m), 6.95(2H, m), 7.17(1H, m), 7.25~7.34(9H, m), 7.41(1H, m), 7.5~7.56(8H, m), 7.63~7.64(3H, m), 7.87(2H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m). 1 H NMR (CDCl 3 , 200 MHz): δ = 0.9 (6H, m), 1.91 (4H, m), 6.95 (2H, m), 7.17 (1H, m), 7.25-7.74 (9H, m), 7.41 (1H, m), 7.5-7.56 (8H, m), 7.63-7.74 (3H, m), 7.87 (2H, m), 7.94 (1H, m), 8.12 (1H, m), 8.55 (1H, m).

MS/FAB: 641.84(found), 641.34(calculated)MS / FAB: 641.84 (found), 641.34 (calculated)

[제조예 2]화합물 92의 제조Preparation Example 2 Preparation of Compound 92

Figure pat00030
Figure pat00030

화합물 A의 제조Preparation of Compound A

4-브로모비페닐 30g(0.12mol)를 1구(one-neck) 플라스크에 넣고 진공 분위기로 만들고 아르곤으로 충전하였다. THF 500ml를 넣고 -78℃에서 10분 간 교반하였다. n-BuLi(2.5M in hexane) 77ml(0.19mol)를 적가하고 1시간 30분간 -78℃에서 교반하였다. 트리메틸보레이트 21.9ml(0.19mol)를 -78℃에서 첨가하였다. 30분간 -78℃에서 교반한 후 실온에서 4시간 동안 교반하였다. 반응이 종결되면 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조시킨 후 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 A 21g(84%)를 분리하였다.30 g (0.12 mol) of 4-bromobiphenyl was placed in a one-necked flask, vacuumed and filled with argon. 500 ml of THF was added and stirred at -78 ° C for 10 minutes. 77 ml (0.19 mol) of n-BuLi (2.5 M in hexane) was added dropwise and stirred at −78 ° C. for 1 hour 30 minutes. 21.9 ml (0.19 mol) of trimethylborate was added at -78 ° C. Stirred at −78 ° C. for 30 minutes and then stirred at room temperature for 4 hours. After the reaction was completed, the mixture was extracted with distilled water and EA. The organic layer was dried over MgSO 4 , and then the solvent was removed using a rotary evaporator, and 21 g (84%) of pure product A was isolated by column chromatography using hexane and EA as developing solvents.

화합물 B의 제조Preparation of Compound B

1-브로모-4-아이오도벤젠 29g(0.10mol)과 화합물 A 21g(0.10mol)와 테트라키스(트리페닐포스핀)팔라듐(Tetrakis(triphenylphosphine)Palladium) 5.9g(5.1mmol)를 2구(Two-neck) 플라스크에 첨가하였다. 톨루엔을 첨가하면서 교반을 시키고 2M K2CO3 265ml(0.5mol)과 에탄올 265ml를 첨가한 후, 100℃에서 5시간동안 환류시켰다. 반응이 종결되면 실온으로 냉각시킨 후 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 B 23g(74%)를 분리하였다.29 g (0.10 mol) of 1-bromo-4-iodobenzene, 21 g (0.10 mol) of Compound A and 5.9 g (5.1 mmol) of Tetrakis (triphenylphosphine) Palladium (2 mmol) Two-neck flask was added. The mixture was stirred while adding toluene, and 265 ml (0.5 mol) of 2M K 2 CO 3 and 265 ml of ethanol were added thereto, and the mixture was refluxed at 100 ° C. for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with distilled water and EA. The organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and 23 g (74%) of pure product B was separated by column chromatography using hexane and EA as developing solvents.

화합물 C의 제조Preparation of Compound C

화합물 B 2g(0.074mol)을 1구(one-neck) 플라스크에 넣고 질소 상태를 만들었다. THF을 첨가한 후 -78℃ 로 온도를 유지한 상태에서 10분간 교반하였다. n-부틸리튬(2.5M in hexane) 44.6ml(0.11mol)를 적가한 후 1시간 동안 -78℃에서 교반하였다. 그 후 DMF 8.1ml(0.11mmol)를 첨가하고 10분 동안 교반한 후 실온에서 4시간 동안 교반하였다. 반응이 종결된 다음 HCl 2.5mL 첨가한 후 실온으로 만든 후 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 C 19g(89%)를 분리하였다.2 g (0.074 mol) of Compound B was placed in a one-neck flask to make nitrogen. After adding THF, it stirred for 10 minutes, maintaining temperature at -78 degreeC. 44.6 ml (0.11 mol) of n-butyllithium (2.5M in hexane) was added dropwise and stirred at -78 ° C for 1 hour. Then 8.1 ml (0.11 mmol) of DMF were added and stirred for 10 minutes, followed by stirring at room temperature for 4 hours. After completion of the reaction, 2.5 mL of HCl was added thereto, and the mixture was brought to room temperature, and extracted with distilled water and EA. The organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and 19 g (89%) of pure product C was isolated by column chromatography using hexane and EA as developing solvents.

화합물 J의 제조Preparation of Compound J

화합물 C 20g(0.077mol)을 1구(one-neck) 플라스크에 넣고 질소 상태를 만들었다. 에탄올 300ml을 첨가한 후 0℃ 로 온도를 유지한 상태에서 10분간 교반하였다. 소듐보로하이드라이드(sodium borohydride) 3.2g(0.085mol)를 첨가한 후 6시간 동안 실온에서 교반하였다. 반응이 종결된 다음 HCl 5mL 첨가한 후 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 J 17.4g(86%)를 분리하였다.20 g (0.077 mol) of Compound C was placed in a one-neck flask to make nitrogen. After 300 ml of ethanol was added, the mixture was stirred for 10 minutes while maintaining the temperature at 0 ° C. 3.2 g (0.085 mol) of sodium borohydride was added, followed by stirring at room temperature for 6 hours. After completion of the reaction, 5mL of HCl was added and extracted with distilled water and EA. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator, and 17.4 g (86%) of pure product J was isolated by column chromatography using hexane and EA as developing solvents.

화합물 K의 제조Preparation of Compound K

화합물 J 15g(0.057mol)과 트리에틸포스파이트 19.4mL(0.12mol)을 1구(one-neck) 플라스크에 첨가하였다. 0℃에서 아이오딘 14.5g(0.057mol)넣고 30분간 교반한 다음, 실온에서 12시간 교반시켰다. 반응이 종결된 후 진공 승화장치로 포스파이트를 제거하고 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 K 16g(72%)을 분리하였다.15 g (0.057 mol) of compound J and 19.4 mL (0.12 mol) of triethylphosphite were added to a one-neck flask. 14.5 g (0.057 mol) of iodine was added at 0 ° C. and stirred for 30 minutes, followed by stirring at room temperature for 12 hours. After the reaction was completed, the phosphite was removed by a vacuum sublimation apparatus, and extracted with distilled water and EA. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator, and 16 g (72%) of pure product K was isolated by column chromatography using hexane and EA as developing solvents.

화합물 L의 제조Preparation of Compound L

1-아미노-4-브로모나프탈렌 60g(0.27mol)를 1구(one-neck) 플라스크에 넣고 진공 분위기로 만들고 아르곤으로 충전하였다. 아세토나이트릴 500ml를 넣고 0℃에서 녹을 때 까지 교반하였다. t-부틸나이트리트 42g(48ml, 0.41mol), 커퍼브롬마이드(copper bromide) 73g(0.32mol)를 첨가하고 실온에서 3시간 동안 교반하였다. 반응이 종결되면 1N HCl 수용액 600ml를 넣고 교반 시킨다 생성된 고체를 여과 한 후 얻은 고체를 증류수와 에테르로 씻어준다. 컬럼을 통하여 으로 순수한 생성물 L 76g(85%)을 얻었다.60 g (0.27 mol) of 1-amino-4-bromonaphthalene was placed in a one-necked flask, vacuumed, and filled with argon. 500 ml of acetonitrile were added and stirred until it melted at 0 ° C. 42 g (48 ml, 0.41 mol) of t-butyl nitrite and 73 g (0.32 mol) of copper bromide were added and stirred at room temperature for 3 hours. After the reaction is completed, add 600 ml of 1N HCl aqueous solution and stir. The resulting solid is filtered, and the obtained solid is washed with distilled water and ether. 76 g (85%) of pure product L was obtained through the column.

화합물 M의 제조Preparation of Compound M

화합물 L 40g(0.12mol)과 카바졸 24.1g(0.14mol), 구리(Cpper) 3.3g(0.05mol)과 18-크라운-6 2.3g(0.009mol), K2CO3 66.3g(0.48mol)를 2구(two-neck) 플라스크에 넣고 진공 분위기로 만들고 아르곤으로 충전하였다. 1,2-디클로로벤젠 250ml를 넣고 180℃에서 6시간 동안 환류시키며 교반하였다. 반응이 종결된 다음 셀라이트 필터를 사용하여 구리를 제거하고 MC로 녹인 후 용매를 제거한 후 디클로로메탄과 헥산을 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물 M 36g(81%)을 분리하였다.Compound L 40g (0.12mol), carbazole 24.1g (0.14mol), copper (Cpper) 3.3g (0.05mol), 18-crown-6 2.3g (0.009mol), 66.3g (0.48mol) K2CO3 The two-neck flask was placed in a vacuum atmosphere and filled with argon. 250 ml of 1,2-dichlorobenzene was added thereto, and the mixture was stirred under reflux at 180 ° C. for 6 hours. After completion of the reaction, copper was removed using a Celite filter, dissolved in MC, and then the solvent was removed. Then, pure product M 36g (81%) was separated by column chromatography using dichloromethane and hexane as a developing solvent.

화합물 N의 제조Preparation of Compound N

화합물 M 20g(0.054mol)을 1구(one-neck) 플라스크에 넣고 질소 분위기로 만들었다. THF를 첨가한 후 -78℃ 로 온도를 유지한 상태에서 10분간 교반하였다. n-부틸리튬(2.5M in hexane) 32ml(0.081mol)를 적가한 후 1시간 동안 -78℃에서 교반하였다. 그 후 DMF 6.3ml(0.081mmol)를 첨가하고 10분 동안 교반한 후 실온에서 4시간 동안 교반하였다. 반응이 종결되면 HCl 3mL 첨가한 후 실온으로 만들고 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조 시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼 크로마토 그래피로 순수한 생성물 N 12.4g(71%)를 분리하였다.20 g (0.054 mol) of Compound M was placed in a one-neck flask and placed in a nitrogen atmosphere. After adding THF, it stirred for 10 minutes, maintaining temperature at -78 degreeC. 32 ml (0.081 mol) of n-butyllithium (2.5 M in hexane) was added dropwise, followed by stirring at −78 ° C. for 1 hour. Then 6.3 ml (0.081 mmol) of DMF were added and stirred for 10 minutes, followed by stirring at room temperature for 4 hours. After the reaction was completed, 3mL of HCl was added, the mixture was brought to room temperature, and extracted with distilled water and EA. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Then, 12.4 g (71%) of pure product N was separated by column chromatography using hexane and EA as developing solvents.

화합물 92의 제조Preparation of Compound 92

화합물 K 10g(0.026mol)과 화합물 N 8.4g(0.026mol)을 1구(one-neck) 플라스크에 넣은 후 진공으로 만든 다음 아르곤 분위기로 만들었다. THF 600mL를 첨가한 후 0℃에서 10분간 교반하고, 포타슘 tert-부톡사이드(1.0M in THF) 31mL(0.031mol)를 천천히 첨가하였다. 0℃에서 10분간 교반하고, 실온에서 3시간동안 교반시켰다. 증류수와 EA로 추출하였다. 유기층을 MgSO4로 건조시킨 다음 회전 증발기로 용매를 제거한 후 헥산과 EA를 전개 용매로 하여 컬럼크로마토그래피로 순수한 생성물인 화합물 92 12g(84%)를 분리하였다.10 g (0.026 mol) of Compound K and 8.4 g (0.026 mol) of Compound N were placed in a one-neck flask, and made into a vacuum, followed by argon atmosphere. After addition of 600 mL of THF, the mixture was stirred at 0 ° C. for 10 minutes, and 31 mL (0.031 mol) of potassium tert-butoxide (1.0 M in THF) was added slowly. Stirred at 0 ° C. for 10 minutes and at room temperature for 3 hours. Extracted with distilled water and EA. The organic layer was dried over MgSO 4 , and the solvent was removed using a rotary evaporator. Then, 12 g (84%) of Compound 92 , a pure product, was separated by column chromatography using hexane and EA as developing solvents.

1H NMR(CDCl3, 200 MHz): δ = 6.95(2H, m), 7.25~7.33(7H, m), 7.41(1H, m), 7.5~7.55(13H, m), 7.9~7.94(3H, m), 8.08~8.12(2H, m), 8.55(1H, m). 1 H NMR (CDCl 3 , 200 MHz): δ = 6.95 (2H, m), 7.25-7.73 (7H, m), 7.41 (1H, m), 7.5-7.55 (13H, m), 7.9-7.94 (3H , m), 8.08-8.12 (2H, m), 8.55 (1H, m).

MS/FAB: 547.69(found), 547.23(calculated).MS / FAB: 547.69 (found), 547.23 (calculated).

상기 제조예 1 및 2의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 90을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다. 하기 표 1에서 "L"은

Figure pat00031
또는
Figure pat00032
를 나타낸다.The organic light emitting compounds 1 to 90 were prepared using the methods of Preparation Examples 1 and 2, and 1 H NMR and MS / FAB of the organic light emitting compounds prepared in Table 1 are shown. "L" in Table 1 is
Figure pat00031
or
Figure pat00032
Indicates.

[표 1]TABLE 1

Figure pat00033
Figure pat00033

Figure pat00034
Figure pat00034

Figure pat00035
Figure pat00035

Figure pat00036
Figure pat00036

Figure pat00037
Figure pat00037

Figure pat00038
Figure pat00038

Figure pat00039
Figure pat00039

[실시예 1-11] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작[Example 1-11] OLED device fabrication 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 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 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, 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 pat00040
Figure pat00040

정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 하기 구조의 DNA(실시예 1 내지 4), H-36(실시예 8 내지 11) 또는 H-38(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. DNA (Examples 1 to 4), H-36 (Examples 8 to 11) or H-38 (Examples 5 to 7) having the following structure as host in one cell in the vacuum deposition apparatus, and another plate After each of the compounds according to the present invention were added as a trace, 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 pat00041
Figure pat00041

이어서 전자전달층으로써 하기 구조의 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 하기 구조의 화합물 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 the following structure was deposited as an electron transport layer to a thickness of 20 nm, and then the compound lithium quinolate (Liq) having the following structure as the electron injection layer was 1 to 2 nm thick. After deposition, the Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to produce an OLED.

Figure pat00042
Figure pat00042

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 pat00043
Figure pat00043

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 내지 11과 비교예 1에서 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.To the above Example 1 to the luminous efficiency of the OLED element, each containing an organic light emitting compound and conventional electroluminescent compounds according to the present invention produced 11 and Comparative Example 1 measured at 1,000 cd / m 2 are shown in Table 2 below.

[표 2]TABLE 2

Figure pat00044
Figure pat00044

상기 표 2에 나타난 바와 같이, 본 발명의 유기 발광 화합물들은 종래의 발광 화합물보다 진한 청색을 구현할 수 있음을 알 수 있었다. 즉, 유기 발광 디스플레이에서 NTSC에 근접한 색을 구현하기 위하여 CIE y = 0.1 정도의 청색이 필요할 때 본 발명의 유기 발광 화합물이 유용하게 쓰일 수 있다.As shown in Table 2, it can be seen that the organic light emitting compounds of the present invention can implement a darker blue than the conventional light emitting compounds. That is, the organic light emitting compound of the present invention may be useful when a blue color of CIE y = 0.1 is required in order to realize a color close to NTSC in the organic light emitting display.

이상에서와 같이 본 발명의 유기 발광 화합물은 고순도의 청색 발광 재료로 사용될 수 있음을 확인하였다. 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 (9)

하기 화학식 1 또는 2로 표시되는 유기발광화합물.
[화학식 1]
Figure pat00045

[화학식 2]
Figure pat00046

[상기 R1 내지 R5는 서로 독립적으로 수소, (C1-C60)알킬, (C3-C60)시클로알킬, (C6-C60)아릴, N, O, S, P, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C2-60)헤테로아릴, (C1-60)알콕시, (C1-C60)알킬티오, (C6-60)아릴옥시, (C6-C60)아릴티오, (C6-30)아릴(C1-C30)알킬아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이고;
X는 화학결합이거나, -(CR6R7)m-, -N(R8)-, -Si(R9)(R10)-, -O-, -S-, -Se- 또는 (R11)C=C(R12)-이고;
R6 내지 R12는 서로 독립적으로 수소, (C1-C60)알킬, (C3-C60)시클로알킬, (C6-C60)아릴, N, O, S, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C2-60)헤테로아릴, (C1-60)알콕시, (C1-C60)알킬티오, (C6-60)아릴옥시, (C6-C60)아릴티오, 모노 또는 디(C1-60)알킬아미노, 모노 또는 디(C6-60)아릴아미노, (C6-30)아릴(C1-C30)알킬아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이거나, R6과 R7, R9와 R10 및 R11와 R12는 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;
Y는 (C6-C60)아릴렌, 아다만틸렌, N, O, S, P, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C3-C60)헤테로아릴렌,
Figure pat00047
또는
Figure pat00048
이고;
Y1은 N, O, S, P, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C2-60)헤테로아릴렌이고;
Z1 및 Z2는 서로 독립적으로 화학결합이거나, -(CR13R14)n-, -N(R15)-, -Si(R16)(R17)-, -O-, -S-, -Se- 또는 (R18)C=C(R19)-이고, 단 Z1 및 Z2는 동시에 화학결합이 아니고
R13 내지 R19는 서로 독립적으로 수소, (C1-C60)알킬, (C3-C60)시클로알킬, (C6-C60)아릴, N, O, S, Si 및 Se로부터 선택된 하나 이상을 포함하는 (C2-60)헤테로아릴, (C1-60)알콕시, (C1-C60)알킬티오, (C6-60)아릴옥시, (C6-C60)아릴티오, 모노 또는 디(C1-60)알킬아미노, 모노 또는 디(C6-60)아릴아미노, (C6-30)아릴(C1-C30)알킬아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴 또는 트리(C6-C30)아릴실릴이거나, R13과 R14, R16와 R17 및 R18와 R19는 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;
a, b 및 c는 서로 독립적으로 1 내지 4의 정수이고;
d는 1 내지 3의 정수이고; 및
m 및 n은 서로 독립적으로 1 내지 4의 정수이다.]An organic light emitting compound represented by the following formula (1) or (2).
[Formula 1]
Figure pat00045

(2)
Figure pat00046

[Wherein R 1 to R 5 are each independently selected from hydrogen, (C 1 -C 60) alkyl, (C 3 -C 60) cycloalkyl, (C 6 -C 60) aryl, N, O, S, P, Si and Se (C2-60) Heteroaryl, (C1-60) Alkoxy, (C1-C60) Alkylthio, (C6-60) Aryloxy, (C6-C60) Arylthio, (C6-30) Aryl (C1) -C30) alkylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri (C6-C30) arylsilyl;
X is a chemical bond, or-(CR 6 R 7 ) m- , -N (R 8 )-, -Si (R 9 ) (R 10 )-, -O-, -S-, -Se- or (R 11 ) C = C (R 12 )-;
R 6 to R 12 independently of one another include at least one selected from hydrogen, (C 1 -C 60 ) alkyl, (C 3 -C 60 ) cycloalkyl, (C 6 -C 60 ) aryl, N, O, S, Si and Se ( C2-60) heteroaryl, (C1-60) alkoxy, (C1-C60) alkylthio, (C6-60) aryloxy, (C6-C60) arylthio, mono or di (C1-60) alkylamino, mono Or di (C6-60) arylamino, (C6-30) aryl (C1-C30) alkylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri ( C 6 -C 30) arylsilyl or R 6 and R 7 , R 9 and R 10 and R 11 and R 12 are (C3-C60) alkylene or (C3-C60) alkenylene with or without fused ring Can be linked to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
Y is a (C3-C60) heteroarylene comprising at least one selected from (C6-C60) arylene, adamantylene, N, O, S, P, Si and Se,
Figure pat00047
or
Figure pat00048
ego;
Y 1 is (C2-60) heteroarylene comprising one or more selected from N, O, S, P, Si and Se;
Z 1 and Z 2 are each independently a chemical bond or-(CR 13 R 14 ) n- , -N (R 15 )-, -Si (R 16 ) (R 17 )-, -O-, -S- , -Se- or (R 18 ) C = C (R 19 )-provided that Z 1 and Z 2 are not chemical bonds at the same time
R 13 to R 19 independently of one another include at least one selected from hydrogen, (C 1 -C 60) alkyl, (C 3 -C 60) cycloalkyl, (C 6 -C 60) aryl, N, O, S, Si and Se ( C2-60) heteroaryl, (C1-60) alkoxy, (C1-C60) alkylthio, (C6-60) aryloxy, (C6-C60) arylthio, mono or di (C1-60) alkylamino, mono Or di (C6-60) arylamino, (C6-30) aryl (C1-C30) alkylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl or tri ( C 6 -C 30) arylsilyl or R 13 and R 14 , R 16 and R 17 and R 18 and R 19 are (C3-C60) alkylene or (C3-C60) alkenylene with or without fused ring Can be linked to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
a, b and c are each independently an integer from 1 to 4;
d is an integer of 1 to 3; And
m and n are each independently an integer from 1 to 4.] 제 1항에 있어서,
상기
Figure pat00049
또는
Figure pat00050
는 하기 구조에서 선택되는 것을 특징으로 하는 유기발광화합물.
Figure pat00051

Figure pat00052

Figure pat00053
The method of claim 1,
remind
Figure pat00049
or
Figure pat00050
The organic light emitting compound, characterized in that selected from the following structure.
Figure pat00051

Figure pat00052

Figure pat00053
 제 1항 또는 제 2항에 따른 유기발광화합물을 포함하는 것을 특징으로 하는 유기발광소자.An organic light emitting device comprising the organic light emitting compound according to claim 1. 제 3항에 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]
(Ar1)e-L1-(Ar2)f
[화학식 4]
(Ar3)g-L2-(Ar4)h
[상기 화학식 3 및 화학식 4에서,
L1는 (C6-C60)아릴렌 또는 (C4-C60)헤테로아릴렌이고;
L2는 안트라세닐렌이며;
Ar1 내지 Ar4은 서로 독립적으로 수소 또는 중수소이거나, (C1-C60)알킬, (C1-C60)알콕시, 할로겐, (C4-C60)헤테로아릴, (C5-C60)시클로알킬 또는 (C6-C60)아릴로부터 선택되고, 상기 Ar1 내지 Ar4의 시클로알킬, 아릴 또는 헤테로아릴은 할로겐이 치환되거나 치환되지 않은 (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 않은 (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;
e, f, g 및 h는 독립적으로 0 내지 4의 정수이다.]The method of claim 3, wherein
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 1 ) e -L 1- (Ar 2 ) f
[Chemical Formula 4]
(Ar 3 ) g -L 2- (Ar 4 ) h
[In Formula 3 and Formula 4,
L 1 is (C6-C60) arylene or (C4-C60) heteroarylene;
L 2 is anthracenylene;
Ar 1 to Ar 4 are independently of each other hydrogen or deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) Is selected from aryl, and the cycloalkyl, aryl or heteroaryl of Ar 1 to Ar 4 is substituted or unsubstituted (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, substituted or unsubstituted halogen, (C1-C60) alkyl, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri One or more substituents selected from the group consisting of (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted;
e, f, g and h are independently integers from 0 to 4. 제 4항에 있어서,
상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 더 포함하는 것을 특징으로 하는 유기 발광 소자. The method of claim 4, wherein
The organic light emitting device further comprises at least one compound selected from the group consisting of an arylamine compound or a styrylarylamine compound in the organic layer. 제 4항에 있어서,
상기 유기물층에 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 4, wherein
The organic light emitting device further comprises at least one metal selected from the group consisting of Group 1, Group 2, 4, 5 cycle transition metals, lanthanide-based metals and organic metal of the d-transition element in the organic layer. 제 4항에 있어서,
상기 유기물층에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 발광 소자.The method of claim 4, wherein
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 4항에 있어서,
상기 유기물층은 발광층 및 전하생성층을 포함하는 것을 특징으로 하는 유기 발광 소자.The method of claim 4, wherein
The organic material layer is an organic light emitting device comprising a light emitting layer and a charge generating layer. 제 4항에 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 4, wherein
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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