KR20110093055A - 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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KR20110093055A
KR20110093055A KR1020100012861A KR20100012861A KR20110093055A KR 20110093055 A KR20110093055 A KR 20110093055A KR 1020100012861 A KR1020100012861 A KR 1020100012861A KR 20100012861 A KR20100012861 A KR 20100012861A KR 20110093055 A KR20110093055 A KR 20110093055A
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substituted
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alkyl
independently
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안희춘
김남균
조영준
권혁주
김봉옥
김성민
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다우어드밴스드디스플레이머티리얼 유한회사
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Priority to PCT/KR2011/000652 priority patent/WO2011099718A1/en
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Abstract

PURPOSE: A novel organic light emitting compound is provided to ensure excellent luminous efficiency and lifetime property of materials and to prepare an organic light emitting diode with improved power consumption. CONSTITUTION: A novel organic light emitting compound is represented by chemical formula 1. In chemical formula 1, A1-A4 are independently CR3 or N; X is - N (R10) -, -S-, -O- or -Si(R11)(R12)-; Y is CR4 or N; Ar1 and Ar2 are independently substituted or unsubstituted (C6-C30) arylene and substituted or unsubstituted (C3-C30) heteroarylene; and Ar3 is independently substituted or unsubstituted (C6-C30) aryl and substituted or unsubstituted (C3-C30) heteroaryl.

Description

신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 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 포함하고 있는 유기 전계 발광 소자에 관한 것으로, 보다 구체적으로는 발광 재료로서 사용되는 신규한 유기 발광 화합물 및 이를 호스트로서 채용하고 있는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly to a novel organic light emitting compound used as a light emitting material and an organic electroluminescent device employing the same as a host.

유기 EL 소자는 전자 주입 전극(음극)과 정공 주입 전극(양극) 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸하면서 빛을 내는 소자이다. 플라스틱 같은 휠 수 있는(flexible) 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널(Plasma Display Panel)이나 무기 EL 디스플레이에 비해 낮은 전압에서 (10V이하) 구동이 가능하고, 또한 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있다. 또한 유기 EL 소자는 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 차세대 풍부한 색 디스플레이 소자로 많은 사람들의 많은 관심의 대상이 되고 있다. An organic EL device is a device that emits light by dissipating electrons and holes after pairing when electrons are injected into the organic film formed between the electron injection electrode (cathode) and the hole injection electrode (anode). The device can be formed on a flexible transparent substrate such as plastic, and can be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic EL display, and also consumes power. It is relatively small and has the advantage of excellent color. In addition, the organic EL device can display three colors of green, blue, and red, and thus, has become a subject of much interest as a next-generation rich color display device.

OLED에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광재료는 기능적인 측면에서 호스트 재료와 도판트 재료로 구분될 수 있는데 일반적으로 EL 특성이 가장 우수한 소자 구조로는 호스트에 도판트를 도핑하여 발광층을 만드는 것으로 알려져 있다. 최근에 고효율, 장수명 유기전계발광소자의 개발이 시급한 과제로 대두되고 있으며, 특히 중대형 OLED 패널에서 요구하고 있는 EL 특성 수준을 고려해 볼 때 기존의 발광재료에 비해 매우 우수한 재료의 개발이 시급한 실정이다.The most important factor determining the luminous efficiency in OLEDs is the luminous material. The light emitting material can be classified into a host material and a dopant material in terms of its function. In general, a device structure having excellent EL characteristics is known to make a light emitting layer by doping a host with a dopant. Recently, the development of high efficiency and long life organic light emitting diodes has emerged as an urgent task. In particular, considering the EL characteristic level required for medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials.

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

본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 기존 호스트 재료에 비해 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수할 뿐만 아니라 전력효율의 상승을 유도하여 소비전력이 개선된 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has better luminous efficiency and excellent life characteristics of the material than the conventional host material to drive the device In addition to having a very long lifespan, there is an advantage of manufacturing an OLED device having improved power consumption by inducing an increase in power efficiency.

[화학식 1][Formula 1]

Figure pat00001
Figure pat00001

[상기 화학식 1에서,[In Formula 1,

A1 내지 A4는 서로 독립적으로 CR3 또는 N이고;A 1 to A 4 are each independently CR 3 or N;

X는 -N(R10)-, -S-, -O- 또는 -Si(R11)(R12)-이며;X is -N (R 10 )-, -S-, -O- or -Si (R 11 ) (R 12 )-;

Y는 CR4 또는 N이고;Y is CR 4 or N;

Ar1 및 Ar2는 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된(C3-C30)헤테로아릴렌이고, Ar3은 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴이며, R1 내지 R4, R10 내지 R12는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 (C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 나이트로, NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si-, R32X-, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐,

Figure pat00002
,
Figure pat00003
또는
Figure pat00004
이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로방향족고리를 형성할 수 있고; 상기 A고리 및 B고리는 각각 독립적으로 치환 또는 비치환된(C5-C30)사이클로알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C6-C30)헤테로아릴이고; 상기 R21 내지 R32는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이며; 상기 Y는 S 또는 O이며; W는 -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- 또는 -B(R58)-이고, R41 내지 R43 및 R51 내지 R58은 상기 R1 내지 R3에서의 정의와 동일하며; 상기 헤테로시클로알킬, 헤테로아릴 및 헤테로방향족고리는 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고; m은 0 내지 2의 정수이며; a, b는 0 내지 4의 정수이며; a, b가 2 이상일 경우에는 서로 동일하거나 상이할 수 있다.]Ar 1 And Ar 2 is independently substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C3-C30) heteroarylene, and Ar 3 is independently substituted or unsubstituted (C6-C30) Aryl, substituted or unsubstituted (C3-C30) heteroaryl, R 1 to R 4 , R 10 to R 12 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocyclo, at least one (C3-C30) cycloalkyl is fused 5- to 7-membered heterocycloalkyl fused with one or more alkyl, substituted or unsubstituted aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, or fused with one or more substituted or unsubstituted aromatic rings ( C3-C30) cycloalkyl, cyano, nitro, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= O) R 27 R 28 , R 29 R 30 R 31 Si-, R 32 X -Substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,
Figure pat00002
,
Figure pat00003
or
Figure pat00004
Or an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings May form a ring; Ring A and ring B are each independently substituted or unsubstituted (C5-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C30) heteroaryl; R 21 to R 32 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; W is-(CR 51 R 52 ) m -,-(R 51 ) C = C (R 52 )-, -N (R 53 )-, -S-, -O-, -Si (R 54 ) (R 55 )-, -P (R 56 )-, -P (= 0) (R 57 )-, -C (= 0)-or -B (R 58 )-, and R 41 to R 43 and R 51 to R 58 is the same as defined above for R 1 to R 3 ; The heterocycloalkyl, heteroaryl and heteroaromatic ring comprises one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; m is an integer from 0 to 2; a, b are integers from 0 to 4; When a and b are 2 or more, they may be the same as or different from each other.]

본 발명에 기재된 ‘알킬’, ‘알콕시’ 및 그 외 ‘알킬’부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함하고, ‘시클로알킬’은 단일 고리계 뿐만 아니라 치환 또는 비치환된 아다만틸 또는 치환 또는 비치환된 (C7-C30)바이시클로알킬과 같은 여러 고리계 탄화수소도 포함한다.Substituents comprising the 'alkyl', 'alkoxy' and other 'alkyl' moieties described herein include both straight or crushed forms, and 'cycloalkyl' is substituted or unsubstituted as well as a single ring system Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl.

본 발명에 기재된 ‘아릴’은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 4 내지 7원, 바람직하게는 5 또는 6원을 포함하는 단일 또는 융합고리계를 포함하며, 하나 이상의 아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. 상기 아릴의 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트라이페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다. 본 발명에 기재된 ‘헤테로아릴’은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원의 단환 헤테로아릴 또는 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. 상기 헤테로아릴기는 고리 내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 상기 헤테로아릴의 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 페나진일, 페노티아진일, 페노옥사진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 디벤조퓨란일, 디벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 카보리닐, 페난트리딘일, 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.'Aryl' described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and includes a single or fused ring system containing 4 to 7 members, preferably 5 or 6 members, and at least one aryl It also includes structures bonded through this chemical bond. Specific examples of the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. Including but not limited to. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. 'Heteroaryl' described in the present invention includes 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. It means an aryl group which is a 5-6 membered monocyclic heteroaryl or polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. In addition, heteroaryl in the present invention also includes a structure in which one or more heteroaryl is bonded through a chemical bond. 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 of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, Monocyclic heteroaryl such as phenazinyl, phenothiazineyl, phenooxazineyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, Dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindolinyl, indolyl, indazolyl, benzothia Polycyclic heteroaryls such as diazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, carborinyl, phenanthridinyl, benzodioxolyl and their corresponding N-oxides (E.g., pyridyl N-oxide, quinolyl N-oxa D), quaternary salts thereof, and the like, but are not limited thereto.

또한, 본 발명에 기재되어 있는 ‘(C1-C30)알킬’기는 (C1-C20)알킬 또는 (C1-C10)알킬을 포함하고, ‘(C6-C30)아릴’기는 (C6-C20)아릴 또는 (C6-C12)아릴을 포함한다. ‘(C3-C30)헤테로아릴’기는 (C3-C20)헤테로아릴 또는 (C3-C12)헤테로아릴을 포함하고, ‘(C3-C30)시클로알킬’기는 (C3-C20)시클로알킬 또는 (C3-C7)시클로알킬을 포함한다. ‘(C2-C30)알케닐 또는 알키닐’기는 (C2-C20)알케닐 또는 알키닐, (C2-C10)알케닐 또는 알키닐을 포함한다.In addition, the '(C1-C30) alkyl' groups described herein include (C1-C20) alkyl or (C1-C10) alkyl, and the '(C6-C30) aryl' group is a (C6-C20) aryl or (C6-C12) aryl. '(C3-C30) heteroaryl' group includes (C3-C20) heteroaryl or (C3-C12) heteroaryl, and the '(C3-C30) cycloalkyl' group is (C3-C20) cycloalkyl or (C3- C7) cycloalkyl. '(C2-C30) alkenyl or alkynyl' groups include (C2-C20) alkenyl or alkynyl, (C2-C10) alkenyl or alkynyl.

또한 본 발명의 ‘치환 또는 비치환된’이라는 기재에서 ‘치환’은 비치환된 치환기에 더 치환되는 경우를 뜻하며, 상기 Ar1 및 Ar3, R1 내지 R4, R10 내지 R12, R21 내지 R32, R41 내지 R43 및 R51 내지 R58에 더 치환되는 치환기는 서로 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된(C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된(C6-C30)아릴, (C6-C30)헤테로아릴이 치환 또는 비치환된(C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된(C3-C30)헤테로아릴, (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, NR61R62, BR63R64, PR65R66, P(=O)R67R68, R69R70R71Si-, R72Z-, R73C(=O)-, R74C(=O)O-, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성할 수 있고; 상기 R61 내지 R72는 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이며; 상기 Z는 S 또는 O이고; 상기 R73 및 R74는 서로 독립적으로 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴 또는 (C6-C30)아릴옥시를 포함한다.In addition, in the description of "substituted or unsubstituted" in the description of "substituted" means a case that is further substituted with an unsubstituted substituent, the Ar 1 And Substituents further substituted with Ar 3 , R 1 to R 4 , R 10 to R 12 , R 21 to R 32 , R 41 to R 43, and R 51 to R 58 may each independently be substituted or unsubstituted with deuterium, halogen, or halogen. Substituted or unsubstituted (C6-C30) aryl, (C6-C30) aryl, (C6-C30) aryl, (C6-C30) heteroaryl substituted or unsubstituted (C6) -C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, aromatic ring at least one fused 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, NR 61 R 62 , BR 63 R 64 , PR 65 R 66 , P ( = O) R 67 R 68 , R 69 R 70 R 71 Si-, R 72 Z-, R 73 C (= O)-, R 74 C (= O) O-, (C2-C30) alkenyl, ( Consisting of C2-C30) alkynyl, cyano, carbazolyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro or hydroxy One or more substituents selected from the group or substituents adjacent to each other may be connected to form a ring; R 61 above To R 72 independently of one another are (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; Z is S or O; R 73 above And R 74 independently of one another includes (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, (C 6 -C 30) aryl or (C 6 -C 30) aryloxy.

보다 구체적으로 본 발명은 하기 화합물로부터 선택되며, 이에 한정되지는 않는다. More specifically, the present invention is selected from the following compounds, but is not limited thereto.

Figure pat00005
Figure pat00005

[Ar1 내지 Ar3, Y, R1, R2, R10 내지 R12, a 및 b는 상기 화학식 1에서의 정의와 동일하다.][Ar 1 To Ar 3 , Y, R 1 , R 2 , R 10 to R 12 , a and b are the same as defined in Formula 1 above.]

상기

Figure pat00006
는 서로 독립적으로 하기 구조에서 선택되며, 이에 한정되지는 않는다.remind
Figure pat00006
Are independently selected from the following structures, but are not limited thereto.

Figure pat00007
Figure pat00007

또한 상기 R1 및 R2는 서로 독립적으로 하기 구조에서 선택되며, 이에 한정되지는 않는다.Also above R 1 And R 2 are independently selected from the following structures, but are not limited thereto.

Figure pat00008
Figure pat00008

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 pat00009
Figure pat00009

Figure pat00010
Figure pat00010

Figure pat00011
Figure pat00011

본 발명에 따른 유기 발광 화합물은 하기 반응식 1에 나타난 바와 같이, 제조될 수 있다.The organic light emitting compound according to the present invention can be prepared as shown in Scheme 1 below.

[반응식 1]Scheme 1

Figure pat00012
Figure pat00012

[상기 반응식 1에서 A1 내지 A4, X, Y, Ar1 내지 Ar3, R1, R2, a 및 b는 상기 화학식 1에서의 정의와 동일하다.][In Scheme 1, A 1 to A 4 , X, Y, Ar 1 to Ar 3 , R 1 , R 2 , a and b are the same as defined in Formula 1 above.]

또한, 본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1의 유기 발광 화합물 하나 이상을 호스트로 하여 하나 이상의 도판트를 포함하는 것을 특징으로 한다. 본 발명의 유기 전계 발광 소자에 적용되는 도판트는 특별히 제한되지는 않으나, 본 발명의 유기 전계 발광 소자에 적용되는 도판트는 하기 화학식 2로 표시되는 화합물로부터 선택되는 것이 바람직하다.In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent 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. The organic material layer may include a light emitting layer, and the light emitting layer may include one or more dopants using at least one organic light emitting compound of Formula 1 as a host. The dopant applied to the organic electroluminescent device of the present invention is not particularly limited, but the dopant applied to the organic electroluminescent device of the present invention is preferably selected from a compound represented by the following formula (2).

[화학식 2][Formula 2]

MM 1One LL 101101 LL 102102 LL 103103

[상기 화학식 2에서,[In the formula (2)

M1은 7족, 8족, 9족, 10족, 11족, 13족, 14족, 15족 및 16족의 금속으로 이루어진 군으로부터 선택되고, 리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되며;M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and ligands L 101 , L 102 and L 103. Are independently selected from the following structures;

Figure pat00013
Figure pat00013

R201 내지 R203은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고; R204 내지 R219는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고; R220 내지 R223은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고; R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고; R227 내지 R229는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;R 201 to R 203 are independently of each other hydrogen, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl; R 204 to R 219 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted Or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen; R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl; R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen; R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;

Q는

Figure pat00014
,
Figure pat00015
또는
Figure pat00016
이며, R231 내지 R242는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된(C6-C30)아릴, 시아노, 치환 또는 비치환된(C5-C30)시클로알킬이거나, 인접한 치환체와 알킬렌 또는 알케닐렌으로 연결되어 스피로 고리 또는 융합고리를 형성할 수 있거나, R207 또는 R208과 알킬렌 또는 알케닐렌으로 연결되어 포화 또는 불포화의 융합고리를 형성할 수 있다.]Q is
Figure pat00014
,
Figure pat00015
or
Figure pat00016
R 231 to R 242 are each independently of the other hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, Cyano, substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or with R 207 or R 208 and alkylene or alkenylene To form a saturated or unsaturated fused ring.]

상기 화학식 2의 도판트 화합물은 하기 구조의 화합물로 예시될 수 있으나 이에 한정하는 것은 아니다.The dopant compound of Formula 2 may be exemplified as a compound having the following structure, but is not limited thereto.

Figure pat00017
Figure pat00017

Figure pat00018
Figure pat00018

본 발명의 유기 전계 발광 소자는 상기 화학식 1의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있으며, 상기 아릴아민계 화합물 또는 스티릴아릴아민계 화합물은 한국특허출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시된 것도 포함하나, 이에 한정되지는 않는다. The organic electroluminescent device of the present invention may include one or more compounds selected from the group consisting of an organic light emitting compound of Formula 1 and an arylamine compound or a styrylarylamine compound, and the arylamine compound Or styrylarylamine-based compounds include, but are not limited to, those exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428.

또한, 본 발명의 유기 전계 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 금속 또는 착체화합물을 더 포함할 수도 있고, 상기 유기물층은 발광층 및 전하생성층을 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in the organic material layer, in addition to the organic light emitting compound of Chemical Formula 1, a group consisting of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element It may further comprise one or more metals or complex compounds selected from, the organic material layer may include a light emitting layer and a charge generating layer.

또한, 상기 유기물층에 상기 유기 발광 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다. 상기 청색, 녹색 또는 적색 발광을 하는 화합물은 한국특허출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In addition, an organic electroluminescent device that emits white light may be formed 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 Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.

본 발명의 유기 전계 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 electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer on at least one inner surface of a pair of electrodes (hereinafter, these are referred to as 'surface layers'). It is preferable to arrange | position the above. 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 전계 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 전계 발광소자를 제작할 수 도 있다.Further, in the organic electroluminescent device of the present invention, disposing 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 the 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. In addition, the reducing dopant layer The white organic electroluminescent device having two or more light emitting layers may be manufactured using the charge generating layer.

본 발명에 따른 유기 발광 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다.The organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent 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 2의 제조Preparation Example 1 Preparation of Compound 2

Figure pat00019
Figure pat00019

화합물 compound 1-11-1 의 제조Manufacture

3-브로모티오펜(3-bormothiophene) 50 g(306 mmol)을 THF 300 mL, 톨루엔 1,200 mL에 녹인 다음 -78 ℃로 냉각하고, n-BuLi 150 mL(2.5M in hexane, 367 mmol)을 첨가하였다. 1시간 동안 교반한 후 -78 ℃로 유지하면서 트라이아이소프로필보레이트(triisopropylborate) 112 mL(490 mmol)을 첨가한 후 10분 간 교반하였다. 반응이 완결되면, H2O를 넣고 EA/H2O로 추출하였다. MgSO4로 수분을 제거하고 감압 증류 후 컬럼(MC/Hexane) 분리하여 화합물 1-1 24 g(60%)을 얻었다.50 g (306 mmol) of 3-bromothiophene was dissolved in 300 mL of THF and 1,200 mL of toluene, cooled to -78 ° C, and 150 mL of n-BuLi (2.5M in hexane, 367 mmol) was added. It was. After stirring for 1 hour, triisopropylborate 112 mL (490 mmol) was added thereto while maintaining at -78 ° C, followed by stirring for 10 minutes. When the reaction was completed, H 2 O was added and extracted with EA / H 2 O. Water was removed with MgSO 4 , distillation under reduced pressure, and column (MC / Hexane) separation were performed to obtain compound 1-1 24 g (60%).

화합물 compound 1-21-2 의 제조Manufacture

화합물 1-1 20.6 g(161 mmol), 2-브로모나이트로벤젠(2-bromonitrobenzene) 25 g(124 mmol), Pd2dba3 1.1 g(1.2 mmol),X-phos 2.4 g(5 mmol), K3PO4 79 g(370 mmol)을 1,4-dioxane 300 mL에 녹이고 하루 동안 환류 교반하였다. 반응이 완료되면 실온에서 식히고, EA/H2O로 추출하였다. MgSO4로 수분을 제거하고 감압 증류 후 컬럼(MC/Hexane) 분리하여 화합물 1-2 23.5 g(92%)을 얻었다. Compound 1-1 20.6 g (161 mmol), 2-bromonitrobenzene 25 g (124 mmol), Pd 2 dba 3 1.1 g (1.2 mmol), X-phos 2.4 g (5 mmol) 79 g (370 mmol) of K 3 PO 4 was dissolved in 300 mL of 1,4-dioxane and stirred at reflux for one day. After the reaction was completed, it was cooled to room temperature and extracted with EA / H 2 O. Water was removed with MgSO 4 , distillation under reduced pressure, and column (MC / Hexane) separation were performed to obtain 23.5 g (92%) of compound 1-2 .

화합물 compound 1-31-3 의 제조Manufacture

화합물 1-2 22.5 g(110 mmol)을 P(OEt)3 500 mL에 녹이고, 4시간 동안 환류 교반한 다음 증류에 의해 P(OEt)3를 제거하여 생긴 적색 액체를 컬럼(EA/Hexane) 분리하여 화합물 1-3 6 g(31%)을 얻었다. Dissolve 22.5 g (110 mmol) of Compound 1-2 in 500 mL of P (OEt) 3 , stir at reflux for 4 hours, and remove P (OEt) 3 by distillation to separate the column (EA / Hexane). To give compound 1-3 6 g (31%).

화합물 compound 1-41-4 의 제조Manufacture

2,4,6-트리클로로피리미딘(2,4,6-trichloropyrimidine) 10 g(54.51 mmol), 페닐보론산 16.6 g(136,29 mmol), Pd(PPh3)4 3.15 g(2.72 mmol), 2M K2CO3 50 mL, 톨루엔 100 mL 및 에탄올 30 mL를 넣고 환류 교반하였다. 4시간 후에 상온으로 냉각하고 증류수를 넣은 다음, EA로 추출하였다. MgSO4로 건조하고 감압 증류 후 컬럼 분리하여 화합물 1-4 7 g(48.%)을 얻었다. 10 g (54.51 mmol) of 2,4,6-trichloropyrimidine, 16.6 g (136,29 mmol) of phenylboronic acid, 3.15 g (2.72 mmol) of Pd (PPh 3 ) 4 50 mL of 2M K 2 CO 3 , 100 mL of toluene and 30 mL of ethanol were added thereto, and the mixture was stirred under reflux. After 4 hours, the mixture was cooled to room temperature, distilled water was added, and extracted with EA. Drying with MgSO 4 , distillation under reduced pressure and column separation yielded Compound 1-4 (7 g, 48.%).

화합물 compound 22 의 제조Manufacture

NaH 1.57 g(39.36 mmol, 60% in mineral oil)을 DMF 70 mL에 넣고, 화합물 1-4 7 g(26.24 mmol)을 DMF 60 mL에 녹여 가하였다. 1시간 후 화합물 1-3 3.8 g(21.87 mmol)을 DMF 70 mL에 녹여 가하였다. 10시간 교반 후 증류수를 넣고 EA로 추출하였다. MgSO4로 건조하고 감압 증류 후 컬럼 분리하여 화합물 2 7 g(56%)을 얻었다. 1.57 g (39.36 mmol, 60% in mineral oil) of NaH was added to 70 mL of DMF, and 7 g (26.24 mmol) of Compound 1-4 was added to 60 mL of DMF. After 1 hour, 3.8 g (21.87 mmol) of compound 1-3 were dissolved in 70 mL of DMF. After stirring for 10 hours, distilled water was added and extracted with EA. Drying with MgSO 4 , distillation under reduced pressure and column separation yielded Compound 2 (7 g, 56%).

[제조예 2] 화합물 17의 제조Preparation Example 2 Preparation of Compound 17

Figure pat00020
Figure pat00020

화합물 compound 2-12-1 의 제조Manufacture

화합물 1-3 5.3 g(30.6mmol), 4-아이오도브로모벤젠(4-iodobromobenzene) 17.3 g(61 mmol), Cu 2.9 g(46mmol), 18-crown-6 0.8 g(3 mmol) 및 K2CO3 12 g(72 mmol)을 1,2-다이클로로벤젠(1,2-dichlorobenzene) 350 mL에 녹인 다음 하루 동안 환류 교반하였다. 반응이 완료되면 cellite를 사용해서 Cu와 base를 제거한 다음, 이 용액을 EA/H2O로 추출하였다. MgSO4로 수분을 제거하고 감압 증류 후 컬럼(MC/Hexane) 분리하여 화합물 2-1 5 g(50%)을 얻었다. Compound 1-3 5.3 g (30.6 mmol), 4-iodobromobenzene 17.3 g (61 mmol), Cu 2.9 g (46 mmol), 18-crown-6 0.8 g (3 mmol) and K 2 12 g (72 mmol) of CO 3 was dissolved in 350 mL of 1,2-dichlorobenzene and stirred under reflux for one day. After completion of the reaction, Cu and base were removed using cellite, and the solution was extracted with EA / H 2 O. Water was removed with MgSO 4 , distillation under reduced pressure, and column (MC / Hexane) separation yielded Compound 2-1 5 g (50%).

화합물 compound 2-22-2 의 제조Manufacture

화합물 2-1 4 g(12 mmol)을 THF 60 mL에 녹인 다음 -78 ℃로 냉각하고, n-BuLi 5.8 mL(2.5M in hexane, 14.4 mmol)을 천천히 첨가 하였다. 1시간 교반한 다음 트라이아이소프로필보레이트(triisopropylborate) 4 mL(19.2 mmol)을 첨가하고 온도를 서서히 올려 실온에서 하루 동안 교반하였다. 반응이 완결되면 2M HCl를 넣고, EA/H2O로 추출하였다. MgSO4로 수분을 제거하고 감압증류 후 컬럼(MC/Hexane) 분리하여 화합물 2-2 2.1 g(60%)을 얻었다.4 g (12 mmol) of Compound 2-1 was dissolved in 60 mL of THF, cooled to -78 ° C, and 5.8 mL (2.5M in hexane, 14.4 mmol) of n-BuLi was added slowly. After stirring for 1 hour, 4 mL (19.2 mmol) of triisopropylborate was added, and the temperature was gradually raised and stirred at room temperature for 1 day. After the reaction was completed, 2M HCl was added and extracted with EA / H 2 O. Water was removed with MgSO 4 , distillation under reduced pressure and column (MC / Hexane) were separated to give 2.1 g (60%) of compound 2-2 .

화합물 compound 2-32-3 의 제조Manufacture

1,3-다이브로모벤젠 11.2 g(47 mmol)을 THF 200 mL에 녹인 다음 -78 ℃로 냉각하고, n-BuLi 19 mL(2.5M in hexane, 70.5 mmol)을 천천히 첨가한 후 1시간 동안 교반하였다. 여기에 TPS-Cl 20 g(56.8 mmol)를 THF 25 mL에 녹인 용액을 천천히 첨가한 후 온도를 서서히 올려 실온에서 하루 동안 교반하였다. 반응이 완결되면 H2O를 넣고 EA/H2O로 추출하였다. MgSO4로 수분을 제거하고, 감압증류 후 컬럼(MC/Hexane) 분리하여 화합물 2-3 17 g(87%)을 얻었다. 11.2 g (47 mmol) of 1,3-dibromobenzene was dissolved in 200 mL of THF, cooled to -78 ° C, and slowly added 19 mL (2.5M in hexane, 70.5 mmol) of n-BuLi, followed by stirring for 1 hour. It was. A solution of 20 g (56.8 mmol) of TPS-Cl in THF 25 mL was slowly added thereto, and the temperature was slowly raised and stirred for 1 day at room temperature. When the reaction was completed, H 2 O was added and extracted with EA / H 2 O. Water was removed with MgSO 4 , distillation under reduced pressure and column (MC / Hexane) were separated to give compound 2-3 17 g (87%).

화합물 compound 2-42-4 의 제조Manufacture

화합물 2-3 17.3 g(41.8 mmol)을 THF 200 mL에 녹인 다음 -78 ℃로 냉각하고, n-BuLi 20 mL(2.5M in hexane, 50 mmol)을 천천히 첨가한 후 1시간 동안 교반하였다. 여기에 트라이메틸보레이트(trimethyl borate) 7 mL(67 mmol)을 천천히 첨가하고 온도를 서서히 올려 실온에서 하루 동안 교반하였다. 반응이 완결되면 2M HCl를 넣고, EA/H2O로 추출하였다. MgSO4로 수분을 제거하고, 감압증류 후 컬럼(MC/Hexane) 분리하여 화합물 2-4 10.5 g(66%)을 얻었다. 17.3 g (41.8 mmol) of Compound 2-3 was dissolved in 200 mL of THF, cooled to -78 ° C, and slowly added 20 mL (2.5M in hexane, 50 mmol) of n-BuLi, followed by stirring for 1 hour. 7 mL (67 mmol) of trimethyl borate was slowly added thereto, and the temperature was slowly raised and stirred for 1 day at room temperature. After the reaction was completed, 2M HCl was added and extracted with EA / H 2 O. Water was removed with MgSO 4 , distillation under reduced pressure and column separation (MC / Hexane) afforded 10.5 g (66%) of compound 2-4 .

화합물 compound 2-52-5 의 제조Manufacture

화합물 2-4 5 g(13 mmol), 2,4-다이클로로피리미딘(2,4-dichloropyrimidine) 1.8 g(12 mmol), Pd(PPh3)4 0.7 g(0.6 mmol) 및 Na2CO3 2.5 g(24 mmol)을 톨루엔 90 mL, EtOH 30 mL, H2O 12 mL에 녹인 다음 80 ℃에서 1.5시간 동안 교반하였다. 반응이 완결되면 EA/H2O로 추출하였다. MgSO4로 수분을 제거하고, 감압증류 후 컬럼(MC/Hexane) 분리하여 화합물 2-5 5 g(93%)을 얻었다. 5 g (13 mmol) of compound 2-4 , 1.8 g (12 mmol) of 2,4-dichloropyrimidine, 0.7 g (0.6 mmol) of Pd (PPh 3 ) 4 and Na 2 CO 3 2.5 g (24 mmol) was dissolved in 90 mL of toluene, 30 mL of EtOH, and 12 mL of H 2 O, followed by stirring at 80 ° C. for 1.5 hours. After the reaction was completed, the mixture was extracted with EA / H 2 O. Water was removed with MgSO 4 , distillation under reduced pressure and column (MC / Hexane) were separated to give 5 g (93%) of compound 2-5 .

화합물 compound 1717 의 제조Manufacture

화합물 2-2 2 g(6.8 mmol), 화합물 2-5 2.8 g(6.2 mmol), Pd(PPh3)4 0.3 g(0.3 mmol) 및 Na2CO3 1.4 g(12.5 mmol)을 톨루엔 50 mL, EtOH 15 mL, H2O 6 mL에 녹인 다음 100 ℃에서 하루 동안 교반하였다. 반응이 완결되면 EA/H2O로 추출하였다. MgSO4로 수분을 제거하고, 감압증류 후 컬럼(MC/Hexane) 분리하여 화합물 17 2 g(60%)을 얻었다.
2 g (6.8 mmol) of compound 2-2 , 2.8 g (6.2 mmol) of compound 2-5 , 0.3 g (0.3 mmol) of Pd (PPh 3 ) 4 and 1.4 g (12.5 mmol) of Na 2 CO 3 were added to 50 mL of toluene, It was dissolved in 15 mL of EtOH and 6 mL of H 2 O, followed by stirring at 100 ° C. for 1 day. After the reaction was completed, the mixture was extracted with EA / H 2 O. Water was removed with MgSO 4 , distillation under reduced pressure and column (MC / Hexane) were separated to give 2 g (60%) of compound 17 .

상기 제조예 1 및 제조예 2의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 68를 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to compound 68 were prepared using the methods of Preparation Example 1 and Preparation Example 2, and 1 H NMR and MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.

[표 1]TABLE 1

Figure pat00021
Figure pat00021

Figure pat00022
Figure pat00022

Figure pat00023
Figure pat00023

Figure pat00024
Figure pat00024

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

본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15 Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 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. 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. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명에 따른 화합물 30을 넣고, 또 다른 셀에는 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 4 내지 10%중량으로 도핑함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 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 OLED소자를 제작하였다. An OLED device having a structure using the light emitting material of the present invention was produced. First, a transparent electrode ITO thin film (15? It was used after. Next, 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. And evacuated until the vacuum in the chamber reached 10 −6 torr, followed by applying a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. N, N '-bis (α- naphthyl) - N, N' to another cell of the vapor deposition devices placed -diphenyl-4,4'-diamine (NPB) , and evaporation of the NPB by applying a current to the cell, the hole injection layer A 20 nm-thick hole transport layer was deposited on top of the hole injection layer and the hole transport layer was then deposited on the light emitting layer as follows: Compound 30 according to the invention as a host in one cell in a vacuum deposition equipment; put, and then in the other cell as a dopant into the Ir (ppy) 3 [tris ( 2-phenylpyridine) iridium] , respectively, the two materials at different rates A light emitting layer of 30 nm thickness was deposited on the hole transport layer by flashing and doping to 4 to 10% by weight, followed by 20 nm thickness of tris (8-hydroxyquinoline) -aluminum (III) (Alq) as an electron transporting layer on the light emitting layer. After depositing, the lithium quinolate (Liq) was deposited with an electron injection layer to a thickness of 1 to 2 nm, and an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device.

재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 OLED 발광재료로 사용하였다.Each compound was vacuum sublimated and purified under 10 -6 torr to be used as an OLED light emitting material.

그 결과, 6.8 V의 전압에서 3.7 mA/cm2의 전류가 흘렀으며, 1060 cd/m2의 녹색발광이 확인되었다.As a result, a current of 3.7 mA / cm 2 flowed at a voltage of 6.8 V, and green light emission of 1060 cd / m 2 was confirmed.

[실시예 2] [Example 2]

발광층에서 호스트 재료로서 화합물 34을 넣고, 발광 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 34 was added as a host material in the emission layer and Ir (ppy) 3 [tris (2-phenylpyridine) iridium] was used as the emission dopant.

그 결과, 6.5 V의 전압에서 3.5 mA/cm2의 전류가 흘렀으며, 1075 cd/m2의 녹색발광이 확인되었다.As a result, a current of 3.5 mA / cm 2 flowed at a voltage of 6.5 V, and green light emission of 1075 cd / m 2 was confirmed.

[실시예 3] Example 3

발광층에서 호스트 재료로서 화합물 51을 넣고, 발광 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 51 was added as a host material in the emission layer and Ir (ppy) 3 [tris (2-phenylpyridine) iridium] was used as the emission dopant.

그 결과, 6.9 V의 전압에서 3.9 mA/cm2의 전류가 흘렀으며, 1070 cd/m2의 녹색발광이 확인되었다.As a result, a current of 3.9 mA / cm 2 flowed at a voltage of 6.9 V, and green light emission of 1070 cd / m 2 was confirmed.

[실시예 4] Example 4

발광층에서 호스트 재료로서 화합물 13을 넣고, 발광 도판트로서 (piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate]을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.OLED device in the same manner as in Example 1, except that Compound 13 was added as a host material in the light emitting layer and (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] was used as the light emitting dopant. Was produced.

그 결과, 7.0 V의 전압에서 13.8 mA/cm2의 전류가 흘렀으며, 1120 cd/m2의 적색발광이 확인되었다.As a result, a current of 13.8 mA / cm 2 flowed at a voltage of 7.0 V, and red light emission of 1120 cd / m 2 was confirmed.

[실시예 5] Example 5

발광층에서 호스트 재료로서 화합물 34를 넣고, 발광 도판트로서 (piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate]을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 34 was added as a host material in the light emitting layer and (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] was used as the light emitting dopant. Was produced.

그 결과, 6.8 V의 전압에서 14.2 mA/cm2의 전류가 흘렀으며, 1095 cd/m2의 적색발광이 확인되었다.As a result, a current of 14.2 mA / cm 2 flowed at a voltage of 6.8 V, and red light emission of 1095 cd / m 2 was confirmed.

[비교예 1] Comparative Example 1

진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 4,4'-bis(carbazol-9-yl)biphenyl(CBP), 도판트로서 Ir(ppy)3[tris(2-phenyl pyridine)iridium]을 이용하고, 정공차단층으로 비스(2-메틸-8-퀴놀리네이토)(p-페닐페놀레이토)알루미늄(III) (BAlq)를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.4,4'-bis (carbazol-9-yl) biphenyl (CBP) as a host material in one cell in a vacuum deposition apparatus, Ir (ppy) 3 [tris (2-phenyl pyridine) iridium as dopant OLED was used in the same manner as in Example 1, except that bis (2-methyl-8-quinolinate) ( p -phenylphenolrato) aluminum (III) (BAlq) was used as the hole blocking layer. The device was produced.

그 결과, 7.5 V의 전압에서 3.8 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 녹색발광이 확인되었다.As a result, a current of 3.8 mA / cm 2 flowed at a voltage of 7.5 V, and green light emission of 1000 cd / m 2 was confirmed.

[비교예 2] Comparative Example 2

진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 4,4'-bis(carbazol-9-yl)biphenyl (CBP), 도판트로서 (piq)2Ir(acac)[bis-(1-phenyl4,4'-bis (carbazol-9-yl) biphenyl (CBP), as a dopant (piq) 2 Ir (acac) [bis- (1- phenyl

isoquinolyl)iridium(III)acetylacetonate]을 이용하고, 정공차단층으로 비스(2-메틸-8-퀴놀리네이토)(p-페닐페놀레이토)알루미늄(III) (BAlq)를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.isoquinolyl) iridium (III) acetylacetonate], except that bis (2-methyl-8-quinolinate) ( p -phenylphenolrato) aluminum (III) (BAlq) was used as the hole blocking layer. An OLED device was manufactured in the same manner as in Example 1.

그 결과, 7.5 V의 전압에서 15.3 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 적색발광이 확인되었다.As a result, a current of 15.3 mA / cm 2 flowed at a voltage of 7.5 V, and red light emission of 1000 cd / m 2 was confirmed.

본 발명에서 개발한 유기 발광 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 발광 화합물을 발광용 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있었다.It was confirmed that the luminescence properties of the organic light emitting compounds developed in the present invention showed superior properties compared to the conventional materials. In addition, the device using the organic light emitting compound according to the present invention as a light emitting host material was not only excellent in the light emission characteristics, but also by lowering the driving voltage to increase the power efficiency to improve the power consumption.

Claims (10)

하기 화학식 1로 표시되는 유기 발광 화합물.
[화학식 1]
Figure pat00025

[상기 화학식 1에서,
A1 내지 A4는 서로 독립적으로 CR3 또는 N이고;
X는 -N(R10)-, -S-, -O- 또는 -Si(R11)(R12)-이며;
Y는 CR4 또는 N이고;
Ar1 및 Ar2는 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된(C3-C30)헤테로아릴렌이고, Ar3은 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴이며, R1 내지 R4, R10 내지 R12는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 (C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 나이트로, NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si-, R32X-, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐,
Figure pat00026
,
Figure pat00027
또는
Figure pat00028
이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로방향족고리를 형성할 수 있고; 상기 A고리 및 B고리는 각각 독립적으로 치환 또는 비치환된(C5-C30)사이클로알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C6-C30)헤테로아릴이고; 상기 R21 내지 R32는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이며; 상기 Y는 S 또는 O이며; W는 -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- 또는 -B(R58)-이고, R41 내지 R43 및 R51 내지 R58은 상기 R1 내지 R3에서의 정의와 동일하며; 상기 헤테로시클로알킬, 헤테로아릴 및 헤테로방향족고리는 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고; m은 0 내지 2의 정수이며; a, b는 0 내지 4의 정수이며; a, b가 2 이상일 경우에는 서로 동일하거나 상이할 수 있다.]An organic light emitting compound represented by Formula 1 below.
[Formula 1]
Figure pat00025

[In the above formula (1)
A 1 to A 4 are each independently CR 3 Or N;
X is -N (R 10 )-, -S-, -O- or -Si (R 11 ) (R 12 )-;
Y is CR 4 or N;
Ar 1 And Ar 2 is independently substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C3-C30) heteroarylene, and Ar 3 is independently substituted or unsubstituted (C6-C30) Aryl, substituted or unsubstituted (C3-C30) heteroaryl, R 1 to R 4 , R 10 to R 12 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocyclo, at least one (C3-C30) cycloalkyl is fused 5- to 7-membered heterocycloalkyl fused with one or more alkyl, substituted or unsubstituted aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, or fused with one or more substituted or unsubstituted aromatic rings ( C3-C30) cycloalkyl, cyano, nitro, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= O) R 27 R 28 , R 29 R 30 R 31 Si-, R 32 X -Substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,
Figure pat00026
,
Figure pat00027
or
Figure pat00028
Or an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings May form a ring; Ring A and ring B are each independently substituted or unsubstituted (C5-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C30) heteroaryl; R 21 to R 32 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; W is-(CR 51 R 52 ) m -,-(R 51 ) C = C (R 52 )-, -N (R 53 )-, -S-, -O-, -Si (R 54 ) (R 55 )-, -P (R 56 )-, -P (= 0) (R 57 )-, -C (= 0)-or -B (R 58 )-, and R 41 to R 43 and R 51 to R 58 is the same as defined above for R 1 to R 3 ; The heterocycloalkyl, heteroaryl and heteroaromatic ring comprises one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; m is an integer from 0 to 2; a, b are integers from 0 to 4; When a and b are 2 or more, they may be the same as or different from each other.] 제 1항에 있어서,
하기 화합물로부터 선택되는 유기 발광 화합물.
Figure pat00029

[Ar1 내지 Ar3, Y, R1, R2, R10 내지 R12, a 및 b는 상기 청구항 제1항의 화학식 1에서의 정의와 동일하다.]The method of claim 1,
An organic light emitting compound selected from the following compounds.
Figure pat00029

[Ar 1 To Ar 3 , Y, R 1 , R 2 , R 10 to R 12 , a and b are the same as defined in Formula 1 of claim 1 above.] 제 1항에 있어서,
상기 Ar1 및 Ar3, R1 내지 R4, R10 내지 R12, R21 내지 R32, R41 내지 R43 및 R51 내지 R58에 더 치환되는 치환기는 서로 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된(C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된(C6-C30)아릴, (C6-C30)헤테로아릴이 치환 또는 비치환된(C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된(C3-C30)헤테로아릴, (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, NR61R62, BR63R64, PR65R66, P(=O)R67R68, R69R70R71Si-, R72Z-, R73C(=O)-, R74C(=O)O-, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성할 수 있고; 상기 R61 내지 R72는 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이며; 상기 Z는 S 또는 O이고; 상기 R73 및 R74는 서로 독립적으로 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴 또는 (C6-C30)아릴옥시인 것을 특징으로 하는 유기 발광 화합물.The method of claim 1,
Ar 1 and Substituents further substituted with Ar 3 , R 1 to R 4 , R 10 to R 12 , R 21 to R 32 , R 41 to R 43, and R 51 to R 58 may each independently be substituted or unsubstituted with deuterium, halogen, or halogen. Substituted or unsubstituted (C6-C30) aryl, (C6-C30) aryl, (C6-C30) aryl, (C6-C30) heteroaryl substituted or unsubstituted (C6) -C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, aromatic ring at least one fused 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, NR 61 R 62 , BR 63 R 64 , PR 65 R 66 , P ( = O) R 67 R 68 , R 69 R 70 R 71 Si-, R 72 Z-, R 73 C (= O)-, R 74 C (= O) O-, (C2-C30) alkenyl, ( Consisting of C2-C30) alkynyl, cyano, carbazolyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro or hydroxy One or more substituents selected from the group or substituents adjacent to each other may be connected to form a ring; R 61 to R 72 independently of one another are (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; Z is S or O; R 73 and R 74 are independently from each other (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl or (C6-C30) aryloxy. 제 1항에 있어서,
상기
Figure pat00030
는 서로 독립적으로 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.
Figure pat00031
The method of claim 1,
remind
Figure pat00030
Are independently selected from the following structures:
Figure pat00031
 제 1항에 있어서,
상기 R1 및 R2는 서로 독립적으로 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.
Figure pat00032
The method of claim 1,
The R 1 And R 2 is independently selected from the following structures.
Figure pat00032
 제 1항 내지 제 5항에서 선택되는 어느 한 항에 따른 유기 발광 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.An organic electroluminescent device comprising the organic light emitting compound according to any one of claims 1 to 5. 제 6항에 있어서,
상기 유기 전계 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 2로 표시되는 도판트 하나 이상을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.
[화학식 2]
M 1 L 101 L 102 L 103
[상기 화학식 2에서,
M1은 7족, 8족, 9족, 10족, 11족, 13족, 14족, 15족 및 16족의 금속으로 이루어진 군으로부터 선택되고, 리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되며;
Figure pat00033

R201 내지 R203은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고; R204 내지 R219는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고; R220 내지 R223은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고; R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고; R227 내지 R229는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;
Q는
Figure pat00034
,
Figure pat00035
또는
Figure pat00036
이며, R231 내지 R242는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된(C6-C30)아릴, 시아노, 치환 또는 비치환된(C5-C30)시클로알킬이거나, 인접한 치환체와 알킬렌 또는 알케닐렌으로 연결되어 스피로 고리 또는 융합고리를 형성할 수 있거나, R207 또는 R208과 알킬렌 또는 알케닐렌으로 연결되어 포화 또는 불포화의 융합고리를 형성할 수 있다.]The method of claim 6,
The organic electroluminescent device includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode, wherein the organic material layer includes one or more organic light emitting compounds and one or more dopants represented by the following Chemical Formula 2. Light emitting element.
(2)
M 1 L 101 L 102 L 103
[In Formula 2,
M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and ligands L 101 , L 102 and L 103. Are independently selected from the following structures;
Figure pat00033

R 201 to R 203 are independently of each other hydrogen, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl; R 204 to R 219 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted Or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen; R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl; R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen; R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q is
Figure pat00034
,
Figure pat00035
or
Figure pat00036
R 231 to R 242 are each independently of the other hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, Cyano, substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or with R 207 or R 208 and alkylene or alkenylene To form a saturated or unsaturated fused ring.] 제 7항에 있어서,
상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물 또는 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속을 더 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The method of claim 7, wherein
At least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound or an organic metal of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and d-transition element in the organic layer The organic electroluminescent device further comprises at least one metal selected from the group consisting of. 제 7항에 있어서,
상기 유기물층은 발광층 및 전하생성층을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The method of claim 7, wherein
The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer. 제 7항에 있어서,
상기 유기물층에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 더 포함하여 백색 발광을 하는 것을 특징으로 하는 유기 전계 발광 소자.The method of claim 7, wherein
The organic light emitting device of claim 1, further comprising at least one organic light emitting layer for emitting blue, red or green light to the organic material layer.
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