KR101511072B1 - The organic electroluminescent device containing the novel organic electroluminescent compounds, and this - Google Patents

The organic electroluminescent device containing the novel organic electroluminescent compounds, and this Download PDF

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KR101511072B1
KR101511072B1 KR20090023944A KR20090023944A KR101511072B1 KR 101511072 B1 KR101511072 B1 KR 101511072B1 KR 20090023944 A KR20090023944 A KR 20090023944A KR 20090023944 A KR20090023944 A KR 20090023944A KR 101511072 B1 KR101511072 B1 KR 101511072B1
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organic electroluminescent
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김치식
조영준
권혁주
김봉옥
김성민
윤승수
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롬엔드하스전자재료코리아유한회사
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Abstract

본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자에 관한 것으로, 보다 상세하게 본 발명에 따른 유기 발광 화합물은 하기 화학식 1 내지 5로부터 선택된다. The present invention, the organic electroluminescent compounds according to the present invention in more detail relates to an organic electroluminescent device containing the novel organic electroluminescent compounds, and it is to be selected from Formulas 1 to 5.
Figure 112014025783015-pat00001
[상기 화학식 1 내지 5에서, X 및 Y는 각각 독립적으로 N(Ar 1 ), O 및 S로부터 선택되고, Ar 1 은 서로 다를 수 있으며, Ar 1 이 복수인 경우 Ar 1 또는 Ar 2 로 표시되며; [In the above Chemical Formulas 1 to 5, X and Y are each independently selected from N (Ar 1), O and S, Ar 1 may be different from each other, in the case where Ar 1 is plural Ar 1 or is represented by Ar 2 .; Z 1 내지 Z 8 은 각각 독립적으로 C(Ar 3 ) 및 N으로부터 선택되고, Ar 3 은 서로 다를 수 있으며, 인접한 Ar 3 는 서로 결합하여 환을 형성할 수 있다.] Z 1 to Z 8 are each independently selected from C (Ar 3) and N, Ar 3 may be different from each other, and adjacent Ar 3 may form a ring by combining with each other.]
본 발명에 따른 유기 발광 화합물은 OLED 소자에서 유기 발광 재료의 호스트 재료로 사용되어 기존 호스트 재료에 비해 발광효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 양호한 OLED를 제조할 수 있는 장점이 있다. The organic electroluminescent compounds according to the invention advantageously can be used in OLED devices as a host material of the organic light emitting material made of an extremely good OLED driving life of the device and excellent life property of good luminous efficiency material compared to conventional host material have.
인광호스트, 유기 발광 화합물, 유기 발광 소자 Phosphorescent host, the organic electroluminescent compounds and organic light-emitting device

Description

신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자{Novel organic electroluminescent compounds and organic electroluminescent device using the same} The novel organic electroluminescent compounds and organic electroluminescent devices comprising the same {Novel organic electroluminescent compounds and organic electroluminescent device using the same}

본 발명은 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 에 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 an organic electroluminescent device containing the novel organic electroluminescent compounds, and this, and more specifically relates to novel organic electroluminescent compounds and organic electroluminescent devices employing the same as the host which are used as a light emitting material.

OLED에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. The most important factor to determine luminous efficiency in an OLED is a light-emitting material. 발광 재료로는 현재까지 형광 재료가 널리 사용되고 있으나, 전기발광의 메커니즘 상 인광 재료의 개발은 이론적으로 4배까지 발광 효율을 개선시킬 수 있는 가장 좋은 방법 중 하나이다. A fluorescent light emitting material, but the material is widely used to date, the development of mechanisms phosphorescent materials for electroluminescent, is one of the best ways to improve the luminous efficiency theoretically up to four times. 현재까지 이리듐(III) 착물 계열이 인광 발광 재료로 널리 알려져 있으며, 각 RGB 별로는 (acac)Ir(btp) 2 , Ir(ppy) 3 및 Firpic 등의 재료가 알려져 있다. To date, iridium (III) complexes are widely known as phosphorescent material, and a material such as the RGB By (acac) Ir (btp) 2 , Ir (ppy) 3 and Firpic known. 특히, 최근 일본, 구미에서 많은 인광 재료들이 연구되어지고 있다. In particular, a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.

Figure 112009016968520-pat00002

인광 발광체의 호스트 재료로는 현재까지 CBP가 가장 널리 알려져 있으며, BCP, BAlq 등의 정공차단층을 적용한 고효율의 OLED가 공지되어 있으며, 일본의 파이오니어 등에서는 BAlq 유도체를 호스트로 이용한 고성능의 OLED가 공지되어 있다. The host material of the phosphorescent light emitting body is CBP is most widely known up to now, BCP, is a highly efficient OLED applying a hole blocking layer, such as BAlq known and are, etc. Japanese Pioneer high performance OLED using a BAlq derivative as the host known It is.

Figure 112009016968520-pat00003

그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변하는 등 단점을 갖고 있다. However, in the conventional materials it has luminescence properties side but the advantageous side, because the thermal stability is very good, a low glass transition temperature, has a disadvantage when subjected to a high temperature deposition process in a vacuum, such as changing the material. OLED에서 전력효율 = (π/전압) × 전류효율 이므로, 전력효율은 전압에 반비례하는데, OLED의 소비 전력이 낮으려면 전력 효율이 높아야 한다. Because power efficiency = (π / voltage) × current efficiency in the OLED, power efficiency is inversely proportional to the voltage, the power consumption of the OLED To obtain a higher power efficiency is low. 실제 인광 발광 재료를 사용한 OLED는 형광 발광 재료를 사용한 OLED에 비해 전류 효율(cd/A)이 상당히 높으나, 인광 발광 재료의 호스트로 BAlq 나 CBP 등 종래의 재료를 사용할 경우, 형광재료를 사용한 OLED에 비해 구동 전압이 높아서 전력 효율(lm/w)면에서 큰 이점이 없었다. The actual phosphorescent material OLED is current efficiency, compared to the OLED using the fluorescent light-emitting material with (cd / A) when the use of extremely high but, BAlq and CBP such conventional materials as a host of the phosphorescent light emitting material, OLED with a fluorescent material than there was a great advantage in terms of the driving voltage is high and the power efficiency (lm / w). 또한, OLED 소자에서의 수명 측면에서도 결코 만족할만한 수준이 되질 못하여 더욱 안정되고, 더욱 성능이 뛰어난 호스트 재료의 개발이 요구되고 있다. Furthermore, in terms of life span of the OLED element is never satisfied with the level being worth more stable mothayeo doejil, there is a need for further development of the excellent performance of the host material.

따라서, 본 발명자들은 상기의 종래의 문제점을 해결하기 위하여 노력한 결과, 발광 효율이 뛰어나고 수명이 획기적으로 개선된 유기 전계 발광 소자를 실현하기 위한 새로운 발광 화합물을 발명하게 되었다. Thus, the present inventors have invented a novel electroluminescent compound for realizing the sought results, the organic electroluminescent device excellent in light emission efficiency improvements in service life are dramatically in order to solve the conventional problems described above.

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. An object of the present invention, good light emission efficiency and lifetime compared to conventional host material in order to solve the above problems, to provide an organic light emitting compound is excellent skeleton having an appropriate color coordinate, and as a further object the light emitting of the organic electroluminescent compounds to provide an organic electroluminescent device having high efficiency and long life is employed as the material.

본 발명은 하기 화학식 1 내지 5로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 기존 호스트 재료에 비해 발광효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 양호한 OLED를 제조할 수 있는 장점이 있다. The present invention is excellent in the organic light-emitting compound is life property of good luminous efficiency material compared to conventional host material according to the present invention relates to an organic electroluminescent device comprising the following general formula 1 to the organic light emitting represented by 5 compound and this element the life of the drive has the advantage that you can prepare a very good OLED.

Figure 112009016968520-pat00004

[상기 화학식 1 내지 5에서, X 및 Y는 각각 독립적으로 N(Ar 1 ), O 및 S로부터 선택되고, Ar 1 은 서로 다를 수 있으며, Ar 1 이 복수인 경우 Ar 1 또는 Ar 2 로 표시되며; [In the above Chemical Formulas 1 to 5, X and Y are each independently selected from N (Ar 1), O and S, Ar 1 may be different from each other, in the case where Ar 1 is plural Ar 1 or is represented by Ar 2 .;

Z 1 Z 1 내지 Z 8 은 각각 독립적으로 C(Ar 3 ) 및 N으로부터 선택되고, Ar 3 은 서로 다를 수 있으며, 인접한 Ar 3 는 서로 결합하여 환을 형성할 수 있으며; To Z 8 are each independently selected from C (Ar 3) and N, Ar 3 may be different from each other, and adjacent Ar 3 may form a ring by combining to each other, and;

Ar 1 Ar 1 및 Ar 2 는 서로 독립적으로 (C1-C60)알킬, (C3-C60)시클로알킬, N, O, S, Si 및 P로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C7-C60)바이시클로알킬, 아다만틸, (C2-C60)알케닐, (C2-C60)알키닐, (C6-C60)아릴 및 (C3-C60)헤테로아릴로부터 선택되며; And Ar 2 are independently a (C1-C60) alkyl, (C3-C60) cycloalkyl, N, O, S, Si, and 5-6 membered heterocycloalkyl of, containing one or more selected from P (C7 one another -C60) alkyl, bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl is selected from;

Ar 3 은 서로 독립적으로 수소, (C1-C60)알킬, 할로겐, 시아노, (C3-C60)시클로알킬, N, O, S, Si 및 P로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤 테로시클로알킬, (C7-C60)바이시클로알킬, 아다만틸, (C2-C60)알케닐, (C2-C60)알키닐, (C6-C60)아릴, (C1-C60)알콕시, (C6-C60)아릴옥시, (C3-C60)헤테로아릴, (C6-C60)아릴티오, (C1-C60)알킬티오, 모노 또는 디(C1-C30)알킬아미노, 모노 또는 디(C6-C30)아릴아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, 모노 또는 디(C6-C30)아릴보라닐, 모노 또는 디(C1-C60)알킬보라닐, 나이트로 및 하이드록시로부터 선택되며; Ar 3 is independently hydrogen, (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, 5-6 membered containing N, O, S, at least one selected from Si and P to each other H. Tero cycloalkyl, (C7-C60) alkyl, bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl, (C1-C60) alkoxy, (C6 -C60) aryloxy, (C3-C60) heteroaryl, (C6-C60) arylthio, (C1-C60) alkylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) aryl amino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, mono or di (C6-C30) aryl boranyl, mono- or di (C1-C60) alkyl boranyl, is selected from nitro, and hydroxy;

상기 Ar 1 내지 Ar 3 의 알킬, 시클로알킬, 헤테로시클로알킬, 바이시클로알킬, 아다만틸, 알케닐, 알키닐, 아릴, 알콕시, 아릴옥시, 헤테로아릴, 아릴티오, 알킬티오, 알킬아미노, 아릴아미노, 트리알킬실릴, 디알킬아릴실릴, 트리아릴실릴, 아릴보라닐 또는 알킬보라닐은 (C1-C60)알킬, 할로겐, 시아노, (C3-C60)시클로알킬, N, O, S, Si 및 P로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C7-C60)바이시클로알킬, 아다만틸, (C2-C60)알케닐, (C2-C60)알키닐, (C6-C60)아릴, (C1-C60)알콕시, (C6-C60)아릴옥시, P(=O)R a R b [R a 및 R b 는 서로 독립적으로 (C1-C60)알킬 또는 (C6-C60)아릴]로 치환된 (C6-C60)아릴, (C3-C60)헤테로아릴, (C6-C60)아릴로 치환된 (C3-C60)헤테로아릴, (C1-C60)알킬로 치환된 (C3-C60)헤테로아릴, (C6-C60)아르(C1-C60)알킬, (C6-C60)아릴티오, (C1-C60)알킬티오, 모 Of said Ar 1 to Ar 3 alkyl, cycloalkyl, heterocycloalkyl, alkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, aryl amino, trialkylsilyl, dialkyl aryl silyl, triarylsilyl, aryl boranyl or alkyl boranyl is (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, N, O, S, Si and 5-6 membered heterocycloalkyl of containing one or more selected from P, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6 -C60) aryl, (C1-C60) alkoxy, (C6-C60) aryloxy, P (= O) R a R b [R a and R b are independently (C1-C60) alkyl or (C6-C60 to each other ) aryl] as a substituted (C6-C60) aryl, (C3-C60) heteroaryl, (C6-C60) aryl (C3-C60) heteroaryl, (C1-C60) a (C3- alkyl substituted by a substituted C60) heteroaryl, (C6-C60) ar (C1-C60) alkyl, (C6-C60) arylthio, (C1-C60) alkylthio, Mo 또는 디(C1-C30)알킬아미노, 모노 또는 디(C6-C30)아릴아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, 모노 또는 디(C6-C30)아릴보라닐, 모노 또는 디(C1-C60)알킬보라닐, 나이트로 및 하이드록시로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있으며; Or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30 ) arylsilyl, mono or di (C6-C30) aryl boranyl, mono- or di (C1-C60) alkyl boranyl, may further be substituted by one or more substituents selected from the group consisting of nitro, and hydroxy, and;

단, X 및 Y가 모두 N(Ar 1 )이고, Z 1 Stage, and both X and Y are N (Ar 1), Z 1 내지 Z 8 이 모두 C(Ar 3 )인 경우는 제외한다.] If to all this the Z 8 C (Ar 3) is excluded.]

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. The substituent that contains the "(C1-C60) alkyl" portion described in the invention may have 1 to 60 carbon atoms, and optionally having from 1 to 20 carbon atoms may have 1 to 10 carbon atoms . "(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. The substituent that contains the "(C6-C60) aryl" are part may have from 6 to 60 carbon atoms, and may have from 6 to 20 carbon atoms, and may have 6 to 12 carbon atoms. "(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) heteroaryl" may have a substituent which is part contains a are from 3 to 60 carbon atoms, may have from 4 to 20 carbon atoms, and may have from 4 to 12 carbon atoms. "(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. "(C3-C60) cycloalkyl" may have been a part contains the number of carbon atoms of 60 to 3 substituents which, may have a 3 to 20 carbon atoms, and may have from 3 to 7 carbon atoms. "(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. "(C2-C60) alkenyl or alkynyl" is part containing the substituent which they may have a 2 to 60 carbon atoms, may have from 2 to 20 carbon atoms, may have 2 to 10 carbon atoms.

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

본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합 고리계를 포함한다. "Aryl" described in the present invention is a single or fused ring containing an organic radical, a 4 to 7 is appropriate in each ring, preferably 5 or 6 ring atoms derived from an aromatic hydrocarbon by removal of one hydrogen and a system. 또한, 하나 이상의 아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. In addition, it includes at least one structure in which an aryl is bonded through a chemical bond. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트라이페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. Inde specific example, phenyl, naphthyl, biphenyl, anthryl, carbonyl and the like (indenyl), fluorenyl, phenanthryl, triphenyl alkylenyl, pyrene days, perylene renil, Cry hexenyl, naphtha hexenyl, fluoran ethenyl but but this is not restrictive.

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. "Heteroaryl" described in the present invention is that comprising from 1 to 4 heteroatoms selected from N, O and S as the aromatic cyclic backbone atoms, and means an aryl group, the remaining aromatic ring backbone atoms are carbon, 5 to 6 a monocyclic heteroaryl group, and a polycyclic heteroaryl group of one or more fused benzene rings, and may be partially saturated. 또한, 하나 이상의 헤테로아릴이 화학결합을 통하여 결합되어 있는 구조도 포함된다. In addition, one or more of the heteroaryl also includes structure which is bonded through a chemical bond. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. Wherein the heteroaryl group is within the heteroatoms are oxidized or four won screen rings, include, for example, the second to form a N- oxide or a quaternary salt aryl group. 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. A specific example furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetra possess, triazolyl, tetrazolyl , Pew Raja carbonyl, pyridyl, pyrazinyl, pyrimidinyl, pyridyl is a monocyclic heteroaryl, such as possess, benzo furyl, benzothienyl, iso-benzo furyl, benzo-imidazolyl, benzo thiazolyl, benzo isothiazolyl, benjoyi rapid-fire group, the turning of benzo-oxazolyl, isobutyl, indolyl, indazolyl, benzo thiadiazolyl, quinolyl, isoquinolyl, new fun carbonyl, quinazolinyl, quinolinyl met my match yet, salicylate quinoxaline carbonyl, carbazolyl, phenanthridine pyridinyl, benzo-dioxide polycyclic heteroaryl and their corresponding N- oxide of such solril (e.g., a pyridyl N- oxide, quinolyl N- oxide), and the like of these quaternary salts, but not limited to, no.

또한, 본 발명의 유기 발광 화합물은 하기 구조의 화합물로 예시될 수 있다. Further, the organic electroluminescent compounds of the invention may be exemplified by compounds of the following structure.

Figure 112009016968520-pat00005

Figure 112009016968520-pat00006

Figure 112009016968520-pat00007

Figure 112009016968520-pat00008

[상기 Ar 1 및 Ar 2 는 상기 화학식 1 내지 5에서의 정의와 동일하다.] [Wherein Ar 1 and Ar 2 is as defined in the formula 1-5.]

또한, 본 발명의 유기 발광 화합물은 하기 구조의 화합물로 예시될 수 있다. Further, the organic electroluminescent compounds of the invention may be exemplified by compounds of the following structure.

Figure 112014025783015-pat00038

Figure 112009016968520-pat00010

[상기 Ar 1 및 Ar 2 는 상기 화학식 1 내지 5에서의 정의와 동일하다.] [Wherein Ar 1 and Ar 2 is as defined in the formula 1-5.]

또한, 본 발명의 유기 발광 화합물은 하기 구조의 화합물로 예시될 수 있다. Further, the organic electroluminescent compounds of the invention may be exemplified by compounds of the following structure.

Figure 112009016968520-pat00011

[상기 Ar 1 는 상기 화학식 1 내지 5에서의 정의와 동일하다.] [Wherein Ar 1 is as defined in the formula 1-5.]

더욱 구체적으로, 상기 Ar 1 및 Ar 2 는 서로 독립적으로 페닐, 1-나프틸, 2- 나프틸이거나, 하기 구조에서 선택되는 치환기이나, 이에 한정되지는 않는다. More specifically, the Ar 1 and Ar 2 is not limited independently phenyl, 1-naphthyl, 2-naphthyl or, substituents selected from the following structures: or, whereby each other.

Figure 112009016968520-pat00012

Figure 112009016968520-pat00013

또한 본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; In addition, the present invention provides an organic electroluminescent device, an organic EL device according to the present invention includes a first electrode; 제2전극; A second electrode; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1 내지 5에서 선택되는 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. And the organic light emitting element composed of at least one organic compound layer interposed between the first electrode and the second electrode, the organic compound layer is characterized in that it comprises at least one organic light-emitting compound selected from the above Chemical Formulas 1 to 5.

본 발명에 따른 유기 전계 발광 소자는 상기 유기물층이 발광층을 포함하며, 상기 발광층은 상기 화학식 1 내지 5에서 선택되는 유기 발광 화합물 하나 이상을 발광 호스트로 하여 하나 이상의 인광 도판트를 포함하며, 상기 발광 도판트는 특 별히 제한되지 않는다. The organic electroluminescent device according to the invention wherein the organic layer comprises an emission layer, the emission layer comprises at least one phosphorescent dopant, and one or more organic electroluminescent compounds as electroluminescent host is selected from the above Chemical Formulas 1 to 5 bit, the light emitting dopant, teuneun not limited specially.

본 발명의 유기 전계 발광 소자에 있어서, 상기 화학식 1 내지 5에서 선택되는 유기 발광 화합물 하나 이상을 포함하고, 동시에 아릴아민계 화합물 및 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 더 포함할 수 있다. In the organic EL device of the present invention, including at least one organic light-emitting compound selected from the above Chemical Formulas 1 to 5, at the same time, an aryl amine compound and styryl aryl contains more amine-based compound at least one compound selected from the group consisting of can do.

또한, 본 발명의 유기 발광 소자에 있어서, 유기물층에 상기 화학식 1 내지 5에서 선택되는 유기 발광 화합물 하나 이상 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열 금속 및 d-전이원소의 유기 금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 상기 유기물층은 발광층 및 전하생성층을 포함할 수 있다. Further, in the organic light emitting device of the present invention, in addition to one or more of the organic light emitting compound selected from the above Chemical Formulas 1 to 5 in the organic layer Group 1, Group 2, 4-cycle, 5 cycles transition metals, lanthanide metals and transition elements d- may further comprise one or more metal or complex compound is selected from the group consisting of an organic metal, the organic layer may comprise an electroluminescent layer and a charge generation layer.

또한, 상기 유기물층에 상기 유기 발광 화합물 이외에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다. Further, it is possible by the said organic layer comprises the organic electroluminescent compounds in addition to blue, red, or more than one organic light emitting layer for the green light emission at the same time to form a white light emitting organic electroluminescent device.

본 발명에 따른 유기 발광 화합물은 OLED 소자에서 유기 발광 재료의 호스트 재료로 사용되어 기존 호스트 재료에 비해 발광효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 양호한 OLED를 제조할 수 있는 장점이 있다. The organic electroluminescent compounds according to the invention advantageously can be used in OLED devices as a host material of the organic light emitting material made of an extremely good OLED driving life of the device and excellent life property of good luminous efficiency material compared to conventional host material have.

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. In the following, a description of the light emitting properties of the organic electroluminescent compounds, methods for their manufacture and the device according to the present example, a representative compound of this invention for a detailed understanding of the invention and are only intended to be illustrative only the exemplary embodiments, the present It not intended to limit the scope of the invention.

[ 제조예 ] [Preparation Example]

[제조예 1] 화합물 A의 제조 [Preparation Example 1] Preparation of Compound A

Figure 112009016968520-pat00014

화합물 A-1의 제조 Preparation of compound A-1

브로모-2-니트로벤젠 30g(148.5mmol), 1-나프탈렌보론산 30.6g(178.2mmol), Pd(PPh 3 ) 4 5.14g(4.45mmol), 2M K 2 CO 3 수용액(297.01mmol), 톨루엔 500mL 및 에탄올 200mL를 넣고 환류교반하였다. Bromo-2-nitro-benzene 30g (148.5mmol), 1- naphthalene boronic acid 30.6g (178.2mmol), Pd (PPh 3) 4 5.14g (4.45mmol), 2M K 2 CO 3 aqueous solution (297.01mmol), toluene put 500mL and 200mL of ethanol was stirred under reflux. 4시간 후 상온으로 냉각시키고 증류수를 넣었다. After 4 hours, cooled to room temperature and added with distilled water. EA로 추출하고 황산마그네슘으로 건조시키고 감압증류하였다. Extracted with EA, dried over magnesium sulphate and evaporated under reduced pressure. 컬럼 분리하여 화합물 A-1 31g(124.3mmol, 84.03%)을 얻었다. Separation column to obtain the title compound A-1 31g (124.3mmol, 84.03%).

화합물 A-2의 제조 Preparation of Compound A-2

화합물 A-1 31g(124.3mmol)과 트리에틸포스파이트 300mL를 넣고 환류 교반하였다. Into the compound A-1 31g (124.3mmol) and triethyl phosphite 300mL was stirred under reflux. 10시간 후 상온으로 냉각시키고 유기 용매를 감압 증류하였다. After 10 hours cooled to room temperature and evaporated the organic solvent under reduced pressure. 증류수를 넣고 EA로 추출하였다. Distilled water was added and extracted with EA. 황산마그네슘으로 건조시키고 감압 증류하였다. Dried over magnesium sulphate and evaporated under reduced pressure. 컬럼 분리하여 화합물 A-2 18g(82.84mmol, 66.81%)을 얻었다. Separation column to obtain the title compound A-2 18g (82.84mmol, 66.81%).

화합물 A-3의 제조 Preparation of Compound A-3

화합물 A-2 18g(82.84mmol), 1,5-디페닐-3-클로로피리딘 26.4g(99.41mmol), Pd(OAc) 2 1.85g(8.28mmol), P(t-bu) 3 8.17ml(16.5mmol, 50% in xylene), NaOt-bu 23.8g(248.5mmol) 및 톨루엔 500mL를 넣고 환류 교반하였다. Compound A-2 18g (82.84mmol), 1,5- diphenyl-3-chloropyridine 26.4g (99.41mmol), Pd (OAc ) 2 1.85g (8.28mmol), P (t-bu) 3 8.17ml ( Insert the 16.5mmol, 50% in xylene), NaOt-bu 23.8g (248.5mmol) and 500mL of toluene was stirred under reflux. 12시간 후 상온으로 냉각시키고 증류수를 넣었다. After 12 hours cooled to room temperature and added with distilled water. EA로 추출하고 황산마그네슘으로 건조시켰다. Extracted with EA and dried with magnesium sulfate. 감압 증류하고 컬럼 분리하여 화합물 A-3 19g(42.54mmol, 51.36%)을 얻었다. It was evaporated under reduced pressure, and the separation column to obtain the title compound A-3 19g (42.54mmol, 51.36%).

화합물 A-4의 제조 Preparation of Compound A-4

화합물 A-3 19g(42.54mmol)을 DMF 200mL에 녹이고 NBS 8.33g(46.80mmol)을 넣었다. Dissolve compound A-3 19g (42.54mmol) in DMF were added to 200mL NBS 8.33g (46.80mmol). 상온에서 10시간 후 후 유기 용매를 감압 증류하였다. At room temperature, it evaporated under reduced pressure an organic solvent and then after 10 hours. 증류수를 넣고 EA로 추출하였다. Distilled water was added and extracted with EA. 황산마그네슘으로 건조시키고 감압 증류하였다. Dried over magnesium sulphate and evaporated under reduced pressure. 컬럼 분리하여 화합물 A-4 20g(38.06mmol, 89.47%)을 얻었다. Separation column to obtain the compound A-4 20g (38.06mmol, 89.47%).

화합물 A-5의 제조 Preparation of Compound A-5

화합물 A-4 20g(38.06mmol)을 THF 200mL에 녹이고 -78℃에서 n-buLi 15.22mL(38.06mmol, 2.5M in hexane)을 천천히 넣었다. The compound A-4 20g (38.06mmol) of n-buLi 15.22mL (38.06mmol, 2.5M in hexane) at -78 ℃ dissolved in 200mL THF was added slowly. 한시간 교반 후 트리메틸보레이트 5.51mL(49.48mmol)를 넣었다. After one hour stirring was added trimethyl borate 5.51mL (49.48mmol). 천천히 상온으로 올리고 12시간 교반하였다. Slowly raised to room temperature and stirred for 12 hours. 증류수를 넣고 EA로 추출하였다. Distilled water was added and extracted with EA. 황산마그네슘으로 건조시키고 감압 증류하였다. Dried over magnesium sulphate and evaporated under reduced pressure. 컬럼 분리하여 화합물 A-5 8g(16.31mmol, 42.86%)을 얻었다. Separation column to obtain the title compound A-5 8g (16.31mmol, 42.86%).

화합물 A-6의 제조 Preparation of Compound A-6

화합물 A-5 8g(16.31mmol), 브로모-2-니트로벤젠 3.95g(19.57mmol), Pd(PPh 3 ) 4 0.56g(0.48mmol), 2M K 2 CO 3 수용액 16mL(32.62mmol), 톨루엔 70mL 및 에탄올 20mL를 넣고 환류 교반하였다. Compound A-5 8g (16.31mmol), bromo-2-nitro-benzene 3.95g (19.57mmol), Pd (PPh 3) 4 0.56g (0.48mmol), 2M K 2 CO 3 aqueous solution of 16mL (32.62mmol), toluene Insert the 70mL and 20mL of ethanol was stirred under reflux. 화합물 A-1 합성과 동일한 방법으로 하여 화합물 A-6 7g(12.33mmol, 75.62%)을 얻었다. In the same manner as compound A-1 synthesis to obtain the title compound A-6 7g (12.33mmol, 75.62%).

화합물 A-7의 제조 Preparation of Compound A-7

화합물 A-6 7g(12.33mmol)을 트리에틸포스파이트 100mL와 섞고 화합물 A-2 합성과 동일하게 하여 화합물 A-7 4g(7.46mmol, 58.33%)을 얻었다. Compound A-6 7g (12.33mmol) of triethyl phosphine in the same manner as sulfite and 100mL mixing compound A-2 synthesis to obtain the compound A-7 4g (7.46mmol, 58.33%).

화합물 A의 제조 Preparation of Compound A

화합물 A-7 4g(7.46mmol), 아이오도벤젠 1.25mL(11.20mmol), 구리분말 0.71g(11.20mmol), K 2 CO 3 3.09g, 18-크라운-6 0.15g(0.59mmol), 1,2-디클로로벤젠 100mL를 섞고 환류 교반하였다. Compound A-7 4g (7.46mmol), iodo-benzene 1.25mL (11.20mmol), copper powder 0.71g (11.20mmol), K 2 CO 3 3.09g, 18- crown -6 0.15g (0.59mmol), 1, mix 2-dichlorobenzene 100mL was stirred under reflux. 15시간 후 상온으로 냉각시켰다. After 15 hours then cooled to room temperature. 유기 용매를 감압 증류하고 증류수를 넣었다. Reduced pressure distillation of the organic solvent and distilled water was added. EA로 추출하고 컬럼 분리하여 화합물 A 3.6g(5.88mmol, 78.88%)을 얻었다. Extracted with EA, and the separation column to obtain a compound A 3.6g (5.88mmol, 78.88%).

[ 제조예 2] 화합물 B의 제조 [Preparation Example 2] Preparation of Compound B

Figure 112009016968520-pat00015

화합물 B-1의 제조 Preparation of compound B-1

1,4-디브로모-2,3-디니트로벤젠 20g(61.36mmol), 1-나프탈렌보론산 26g(153.42mmol), Pd(PPh 3 ) 4 3.54g(3.06mmol), 2M K 2 CO 3 수용액 90mL, 톨루엔 200mL 및 에탄올 100mL를 섞고 환류 교반하였다. 1,4-dibromo-2,3-dinitrobenzene 20g (61.36mmol), 1- naphthalenesulfonic acid 26g (153.42mmol), Pd (PPh 3) 4 3.54g (3.06mmol), 2M K 2 CO 3 mixing an aqueous solution of 90mL, 200mL of toluene and 100mL of ethanol was stirred under reflux. 10시간 후에 상온으로 냉각시키고 증류수를 넣고 EA로 추출하였다. After 10 hours into the cooled to room temperature and distilled water and extracted with EA. 황산마그네슘으로 건조시키고 감압 증류하였다. Dried over magnesium sulphate and evaporated under reduced pressure. 컬럼 분리하여 화합물 B-1 22g(52.32mmol, 85.28%)을 얻었다. Separation column to obtain the compound B-1 22g (52.32mmol, 85.28%).

화합물 B-2의 제조 Preparation of compound B-2

화합물 B-1 22g(52.32mmol)과 트리에틸포스파이트 200mL를 섞고 180℃로 교반하였다. Compound B-1 22g (52.32mmol) and tri-ethyl phosphite 200mL mix and the mixture was stirred with 180 ℃. 화합물 A-2 합성과 동일하게 하여 화합물 B-2 10g(28.05mmol, 53.95%)을 얻었다. In the same manner as compound A-2 synthesis to obtain the compound B-2 10g (28.05mmol, 53.95%).

화합물 B-3의 제조 Preparation of compound B-3

화합물 B-2 10g(28.05mmol), 2-아이오도나프탈렌 7.1g(28.05mmol), 구리 분말 2.67g(42.08mmol), K 2 CO 3 11.63g(84.17mmol), 18-크라운-6 0.59g(2.24mmol), 1,2-디클로로벤젠 100mL를 섞고 190℃로 20시간 교반하였다. Compound B-2 10g (28.05mmol), 2- iodo-naphthalene 7.1g (28.05mmol), copper powder 2.67g (42.08mmol), K 2 CO 3 11.63g (84.17mmol), 18- crown -6 0.59g ( 2.24mmol), mix and 100mL 1,2-dichlorobenzene was stirred for 20 hours at 190 ℃. 상온으로 냉각시키고 유기 용매를 감압증류하였다. It cooled to room temperature and evaporated the organic solvent under reduced pressure. 증류수를 넣고 EA로 추출하였다. Distilled water was added and extracted with EA. 황산마그네슘으로 건조시키고 감압증류하였다. Dried over magnesium sulphate and evaporated under reduced pressure. 컬럼 분리하여 화합물 B-3 4g(8.28mmol, 29.60%)을 얻었다. Separation column to obtain a compound B-3 4g (8.28mmol, 29.60%).

화합물 B의 제조 Preparation of Compound B

화합물 B-3 4g(8.28mmol)을 DMF 20mL에 녹여서 NaH 0.49g(12.43mmol, 60% dispersion in mineral oil)가 DMF 20mL에 녹아 있는 반응 용기에 넣었다. Dissolving the compound B-3 4g (8.28mmol) in 20mL DMF is NaH 0.49g (12.43mmol, 60% dispersion in mineral oil) was charged to a reaction vessel, dissolved in 20mL DMF. 한 시간 후 2-클로로-4,6-디페닐트리아진 2.66g(9.94mmol)을 DMF 20mL에 녹여서 넣었다. After an hour, it was added by dissolving the 2-chloro-4,6-diphenyl-triazine 2.66g (9.94mmol) in 20mL DMF. 12시간 교반한 후 증류수를 넣고 생성된 고체를 감압 여과하였다. After stirring for 12 hours the resulting solid was filtered distilled water under reduced pressure. EA 및 DMF로 재결정하여 화합물 B 3.5g(4.90mmol, 59.21%)을 얻었다. Recrystallized from EA and DMF to give Compound B 3.5g (4.90mmol, 59.21%).

[제조예 3] 화합물 C의 제조 [Preparation Example 3] Preparation of Compound C

Figure 112009016968520-pat00016

화합물 C-1의 제조 Preparation of compound C-1

1,2-시클로헥실디온 42.52g(379.26mmol)을 에탄올 1000mL에 녹이고 2-나프틸하드라진 20g(126.42mmol)을 천천히 넣었다. Dissolve 1,2-cyclohexyl dione 42.52g (379.26mmol) in 1000mL of ethanol was added slowly to 2-naphthyl hard l 20g (126.42mmol). 아세트산 0.28mL(5.05mmol)를 넣고 40℃로 가열하였다. Put ethyl 0.28mL (5.05mmol) was heated to 40 ℃. 2시간 후 냉각시키고 증류수를 넣고 생성된 고체를 감압 여과하였다. After 2 hours, then cooled and filtered under reduced pressure, the resulting solid into the distilled water. 화합물 C-1 17g(67.37mmol, 53.47%)을 얻었다. Compound C-1 17g (67.37mmol, 53.47%) was obtained.

화합물 C-2의 제조 Preparation of compound C-2

화합물 C-1 17g(67.37mmol)을 아세트산 100mL에 녹이고 트리플루오로아세트산 10mL를 넣었다. Dissolve the compound C-1 17g (67.37mmol) in 100mL ethyl acetate was added to 10mL of trifluoroacetic. 상온에서 2시간 교반한 후 증류수를 넣었다. After stirring at room temperature for 2 hours, distilled water was added. NaOH 수용액으로 중성화시킨 후 EA로 추출하였다. After neutralization with aqueous NaOH solution and extracted with EA. 황산마그네슘으로 건조시켰다. Dried over magnesium sulfate. 감압 증류하고 컬럼 분리하여 화합물 C-2 11g(46.75mmol, 69.39%)을 얻었다. It was distilled off under reduced pressure and separated by column to give the compound C-2 11g (46.75mmol, 69.39%).

화합물 C-3의 제조 Preparation of compound C-3

화합물 B-3합성과 동일하게 하여 화합물 C-3 10g(32.11mmol, 68.69%)을 얻었다. Compound B-3 In the same manner as in Synthesis C-3 10g (32.11mmol, 68.69%) was obtained.

화합물 C-4의 제조 Preparation of compound C-4

화합물 C-1 합성과 동일하게 하여 화합물 C-4 12g(29.88mmol, 93.07%)을 얻었다. Compound C-1 in the same manner as in the synthesis to obtain the compound C-4 12g (29.88mmol, 93.07%).

화합물 C-5의 제조 Preparation of compound C-5

화합물 C-2 합성과 동일하게 하여 화합물 C-5 6g(15.68mmol, 52.50%)을 얻었다. Compound C-2 in the same manner as in the synthesis to obtain the compound C-5 6g (15.68mmol, 52.50%).

화합물 C의 제조 Preparation of Compound C

화합물 B 합성과 동일하게 하여 화합물 C 5g(8.14mmol, 51.95%)을 얻었다. In the same manner as compound B synthesis to obtain the title compound C 5g (8.14mmol, 51.95%).

[제조예 4] 화합물 D의 제조 [Preparation Example 4] Preparation of Compound D

Figure 112009016968520-pat00017

화합물 D-2의 제조 Preparation of compound D-2

화합물 D-1을 이용하여 화합물 A-1과 동일한 방법으로 화합물 D-2 11g(38.02mmol, 89.22%)을 제조하였다. Compound D-1 and the compound A-1 and the compound D-2 11g (38.02mmol, 89.22%) by the same method used to prepare.

화합물 D-3의 제조 Preparation of Compound D-3

화합물 A-2과 동일한 방법으로 화합물 D-3 8g(31.09mmol, 81.78%)을 제조하였다. Compound D-3 8g (31.09mmol, 81.78%) was prepared in the same manner as compound A-2.

화합물 D의 제조 Preparation of Compound D

화합물 B과 동일한 방법으로 화합물 D 6g(12.30mmol, 38.70%)을 제조하였다. By the same method as compound B the compound D 6g (12.30mmol, 38.70%) was prepared.

[제조예 5] 화합물 E 및 F의 제조 [Preparation Example 5] Preparation of Compound E and F

Figure 112009016968520-pat00018

화합물 E-2의 제조 Preparation of Compound E-2

화합물 E-1을 이용하여 화합물 A-1과 동일한 방법으로 화합물 E-2 15g(51.85mmol, 86.51%)을 제조하였다. The compound E-1 by using the compound in the same manner as compound A-1 E-2 15g (51.85mmol, 86.51%) was prepared.

화합물 E-3의 제조 Preparation of compound E-3

화합물 A-2과 동일한 방법으로 화합물 E-3 6g(23.31mmol, 44.97%)을 제조하였다. Compound A-2 and compound E-3 6g (23.31mmol, 44.97%) was prepared in the same manner.

화합물 E의 제조 Preparation of Compound E

화합물 B과 동일한 방법으로 화합물 E 5g(10.25mmol, 43.99%)을 제조하였다. The same manner as Compound B Compound E 5g (10.25mmol, 43.99%) was prepared.

화합물 F-1의 제조 Preparation of compound F-1

화합물 A-2과 동일한 방법으로 화합물 F-1 3g(11.65mmol, 22.48%)을 제조하였다. In the same manner as compound A-2 was prepared in the compound F-1 3g (11.65mmol, 22.48%).

화합물 F의 제조 Preparation of Compound F

화합물 B과 동일한 방법으로 화합물 F 3g(6.15mmol, 52.81%)을 제조하였다. The same manner as Compound B Compound F 3g (6.15mmol, 52.81%) was prepared.

[제조예 6] 화합물 G 및 H의 제조 [Preparation Example 6] Preparation of Compound G and H

Figure 112009016968520-pat00019

화합물 G-1의 제조 Preparation of Compound G-1

카바졸 20g(119.6mmol), 아이오도벤젠 20mL(179.41mmol), 구리 11.4g(179.41mmol), K 2 CO 3 49g(358.8mmol), 18-크라운-6 2.5g(9.56mmol), 1,2-디클로로벤젠 600mL를 넣고 190℃로 12시간 교반하였다. Carbazole 20g (119.6mmol), iodo-benzene, 20mL (179.41mmol), copper 11.4g (179.41mmol), K 2 CO 3 49g (358.8mmol), 18- crown -6 2.5g (9.56mmol), 1,2 - Place a 600mL-dichlorobenzene was stirred for 12 hours at 190 ℃. 상온으로 냉각시키고 감압 증류하였다. Cooled to room temperature and distilled under reduced pressure. 증류수를 넣고 EA로 추출하였다. Distilled water was added and extracted with EA. 황산마그네슘으로 건조시키고 감압 증류하였다. Dried over magnesium sulphate and evaporated under reduced pressure. 컬럼 분리하여 화합물 G-1 22g(90.42mmol, 75.60%)을 얻었다. Separation column to obtain the title compound G-1 22g (90.42mmol, 75.60%).

화합물 G-2의 제조 Preparation of compound G-2

화합물 A-4과 동일한 방법으로 화합물 G-2 25g(77.59mmol, 85.81%)을 제조하였다. The compound in the same manner as in compound A-4 G-2 25g (77.59mmol, 85.81%) was prepared.

화합물 G-3의 제조 Preparation of Compound G-3

화합물 A-5과 동일한 방법으로 화합물 G-3 11g(38.31mmol, 49.37%)을 제조하였다. The compound in the same manner as compound A-5 G-3 11g (38.31mmol, 49.37%) was prepared.

화합물 G-4의 제조 Preparation of compound G-4

화합물 A-1과 동일한 방법으로 화합물 G-4 12g(32.84mmol, 85.72%)을 제조하였다. The compound in the same manner as compound A-1 G-4 12g (32.84mmol, 85.72%) was prepared.

화합물 G-5의 제조 Preparation of compound G-5

화합물 A-2과 동일한 방법으로 4시간 동안 반응시켜 화합물 G-5 6g(17.99mmol, 54.80%)을 제조하였다. Reacting for 4 hours in the same manner as compound A-2 was prepared in the compound G-5 6g (17.99mmol, 54.80%).

화합물 G의 제조 Preparation of Compound G

화합물 B과 동일한 방법으로 화합물 G 7g(12.39mmol, 68.91%)을 제조하였다. The same manner as compound B G 7g compound (12.39mmol, 68.91%) was prepared.

화합물 H-1의 제조 Preparation of compound H-1

화합물 A-2과 동일한 방법으로 4시간 동안 반응시켜 화합물 H-1 2g(5.99mmol, 18.26%)을 제조하였다. Reacting for 4 hours in the same manner as compound A-2 compound was prepared with H-1 2g (5.99mmol, 18.26%).

화합물 H의 제조 Preparation of Compound H

화합물 B과 동일한 방법으로 화합물 H 1.7g(3.01mmol, 50.26%)을 제조하였다. By the same method as Compound B Compound H 1.7g (3.01mmol, 50.26%) was prepared.

상기 제조예 1 내지 6의 방법을 이용하여 유기 발광 화합물(TA, TB 및 TC)을 제조하였으며, 표 1 및 표 2에 제조된 유기 발광 화합물들의 치환기 Ar 1 및 Ar 2 , 1 H NMR 및 MS/FAB를 나타내었다. Preparative Example 1 to using a sixth method of the final compound to the organic light emitting compound (TA, TB and TC), Table 1, and the substituent of the organic electroluminescent compounds prepared are shown in Table 2 Ar 1 and Ar 2, 1 H NMR and MS / It showed a FAB.

[표 1] TABLE 1

Figure 112009016968520-pat00020

Figure 112009016968520-pat00021

Figure 112009016968520-pat00022

Figure 112009016968520-pat00023

Figure 112009016968520-pat00024

Figure 112009016968520-pat00025

Figure 112009016968520-pat00026

Figure 112009016968520-pat00027

[표 2] TABLE 2

Figure 112009016968520-pat00028

Figure 112009016968520-pat00029

Figure 112009016968520-pat00030

[실시예 1 내지 10] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작 [Example 1-10] Production OLED device employing the organic electroluminescent compounds according to the invention

본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. An OLED device having a structure using a light-emitting material of the present invention was produced. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명 전극 ITO 박막(15 Ω/□) 을, 트리클로로에틸렌, 아세톤, 에탄올 및 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. First, a glass (Samsung-Corning Co.) for the OLED a transparent electrode ITO thin film (15 Ω / □) obtained from, with the ethylene, acetone, ethanol and distilled water, trichloromethyl used sequentially after performing an ultrasonic cleaning, which put it in isopropanol storage and then it was used. 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. Then, an ITO substrate was equipped in a substrate folder of a vacuum vapor-deposit device, and to the cell structure of 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) of the vacuum vapor-deposit device triphenylamine (2 -TNATA) were dissolved, was evacuated until the degree of vacuum in the chamber reaches 10 -6 torr, to evaporate 2-TNATA to the current applied to the cell was deposited 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)' and evaporated to vapor-deposit of a hole transport layer of 20 nm of thickness on the hole injection layer.

Figure 112009016968520-pat00031

진공 증착 장비 내의 한쪽 셀에 호스트 재료로 10 -6 torr하에서 진공 승화 정제된 본 발명에 따른 화합물(예 :화합물 TA8-H4-H2)을 넣고, 다른쪽 셀에는 발광 도판트(예 :화합물 (piq) 2 Ir(acac))를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 4 내지 10mol%로 도핑함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다. The compounds according to the invention under 10 -6 torr with a host material in one cell of a vacuum sublimation purification in a vacuum vapor-deposit device (e.g., a compound TA8-H4-H2) placed, and the other cell is light-emitting dopant (e.g., compound (piq ) 2 Ir (acac)), respectively, insert, and evaporated at different rates, the two materials were deposited an electroluminescent layer having 30 nm of thickness on the hole transport layer by doping with 4 to 10mol%.

Figure 112009016968520-pat00032

이어서 전자전달층으로서 하기 구조의 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로서 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. Then tris the following structure as an electron transport layer (8-hydroxyquinoline) -aluminum (III) (Alq) was deposited to a thickness of 20 nm, and then, the following structure as an electron injection layer, the compound lithium quinolate (Liq) from 1 to 2 nm thick depositing a post, an Al cathode to manufacture an OLED deposited to a thickness of 150 nm by using another vacuum vapor-deposit device.

Figure 112009016968520-pat00033

[실시예 11 내지 20] 본 발명에 따른 전기 발광 화합물을 이용한 OLED 소자의 제조 [Examples 11 to 20] Manufacture of OLED device using the electroluminescent compound according to the invention

호스트 재료로서 본 발명에 따른 화합물(예 :화합물 TA4-H4-H4)을 이용하고, 발광 도판트로서 하기 화학식의 유기 이리듐 착물(Ir(ppy) 3 )을 이용한 것 외에는, 실시예 1 내지 10의 OLED 소자와 마찬가지로 OLED 소자를 제작하였다. As the host material, the compounds according to the invention (e.g., compound TA4-H4-H4), except for using the use of, and to a light emitting dopant, the organic iridium complex of the formula (Ir (ppy) 3), of Example 1-10 the OLED device was manufactured as in the OLED element.

Figure 112009016968520-pat00034

[비교예 1 및 2] 종래의 발광 재료를 이용한 OLED 소자 제작 [Comparative Examples 1 and 2] Production OLED device using a conventional luminescent material

진공 증착 장비 내의 다른 셀에 발광 호스트 재료로서 본 발명에 따른 전기 발광 화합물 대신에 Bis(2-methyl-8-quinolinato)(p-phenylphenolato) aluminum(III)(BAlq)을 넣은 것 이외에는 실시예 1 및 실시예 11과 동일하게 OLED 소자를 제작하였다. Carried out except that into the Bis (2-methyl-8-quinolinato) instead of the electroluminescent compound according to the invention as electroluminescent host material to another cell of the vacuum vapor-deposit device (p-phenylphenolato) aluminum (III) (BAlq) Examples 1 and in the same manner as in example 11 to manufacture an OLED device.

Figure 112009016968520-pat00035

본 발명에 따른 유기 발광 화합물을 함유하는 실시예 1 내지 실시예 10 및 실시예 11 내지 실시예 20의 OLED 소자와 비교예 1 및 2에서 제조된 종래의 발광 화합물을 함유하는 OLED 소자의 구동전압 및 전력효율을 1,000 cd/㎡에서 측정하여 각각 하기 표 3 및 표 4에 나타내었다. The driving voltage of the OLED device containing the organic electroluminescent compound in Examples 1 to 10 and carrying out the OLED element in Comparative Examples 1 and 2, a conventional light-emitting compound prepared in the Example 11 to Example 20 which contains according to the invention and to respectively measure the power efficiency at 1,000 cd / ㎡ shown in Table 3 and Table 4.

하기의 표 3 및 표 4로부터 본 발명에서 개발한 유기발광 화합물들이 성능 측면에서 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있다. From the following Table 3 and Table 4, it can be confirmed that exhibit superior properties compared to conventional materials in terms of performance to a organic electroluminescent compounds developed by the present invention.

[표 3] TABLE 3

Figure 112009016968520-pat00036

[표 4] TABLE 4

Figure 112009016968520-pat00037

상기 표 3으로부터 본 발명에서 개발한 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. Light-emitting characteristics of the compounds developed by the present invention from the above Table 3 was confirmed to exhibit superior properties compared to conventional materials. 종래의 재료인 비교예 1의 소 자에 비해 우수한 전류특성을 가져 1V 이상 낮아진 구동전압을 나타냈으며, 우수한 발광특성으로 인해 비교예 1의 소자에 비해 1.4배 이상의 높은 전력효율 특성을 나타냈다. Exhibited excellent obtain the current characteristics exhibited a lower driving voltage than 1V, excellent light-emitting property at a high power efficiency characteristic more than 1.4 times compared to the device of Comparative Example 1 because of the comparison of Comparative Example 1, conventional materials lowercase.

또한 상기 표 4로부터 본 발명에서 개발한 화합물들을 녹색 발광용 호스트 재료로 사용하는 경우, 우수한 발광특성으로 인해 비교예 2의 소자에 비해 1.6배 이상의 월등히 높은 전력효율 특성을 나타냈다. Also it is shown the case from Table 4 to use a compound developed by the present invention as a host material for the green emission, an excellent light emitting property in Comparative Example 2, the device of much higher power efficiency characteristics than 1.6 times compared to the result. 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. The light emission characteristics were confirmed to exhibit superior properties compared to conventional materials. 특히, 실시예 14의 경우 비교예1의 소자에 비해 2.7V 낮은 전압에서 구동 되었으며, 실시예 17의 소자의 경우 5.5V의 구동전압 및 1000 cd/m2에서 15.9 lm/W의 전력효율을 나타내었다. In particular, Example 14 of the case than the device of Comparative Example 1 was driven at a low voltage 2.7V, 5.5V embodiment showed the example 17 the drive voltage and power efficiency at 1000 cd / m2 15.9 lm / W in the case of the device .

따라서, 본 발명에 따른 전기 발광 화합물을 적색 및 녹색 발광용 호스트 재료로 사용한 소자는 발광특성이 뛰어나며, 또한 구동전압을 강하시켜줌으로써, 특히 녹색 발광용 소자의 경우 5.1~7.7 lm/W의 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있다. Accordingly, the device using the electroluminescent compound according to the invention with the red and green luminescent host material for the excellent light emitting property, in the case of by giving lowers the driving voltage, particularly a green light emitting element for the 5.1 ~ 7.7 lm / W of power efficiency the induction of the increase can improve the power consumption.

Claims (10)

  1. 하기 화학식 1의 유기 발광 화합물. The organic electroluminescent compounds of the formula (I).
    [화학식 1] Formula 1
    Figure 112014111295299-pat00039
    [상기 화학식 1에서, X 및 Y는 각각 독립적으로 N(Ar 1 ), O 및 S로부터 선택되고, X 및 Y 중 적어도 하나는 N(Ar 1 )이고, Ar 1 은 서로 다를 수 있으며, Ar 1 이 복수인 경우 Ar 1 또는 Ar 2 로 표시되며; [In Formula 1, X and Y are each independently N (Ar 1), O, and is selected from S, at least one of X and Y is N (Ar 1), and, Ar 1 may be different from each other, Ar 1 when a plurality of, and represented by Ar 1 or Ar 2;
    Z 1 내지 Z 8 은 각각 독립적으로 C(Ar 3 ) 및 N으로부터 선택되고, Ar 3 은 서로 다를 수 있으며, 인접한 Ar 3 는 서로 결합하여 환을 형성할 수 있으며; Z 1 to Z 8 are each independently selected from C (Ar 3) and N, Ar 3 may be different from each other, and adjacent Ar 3 may form a ring by combining to each other, and;
    Ar 1 은 치환 또는 비치환된 (C6-C60)헤테로아릴로 치환된 (C6-C60)아릴, 또는 치환 또는 비치환된 (C6-C60)헤테로아릴이고; Ar 1 is a substituted or unsubstituted (C6-C60) substituted with a heteroaryl (C6-C60) aryl, or a substituted or unsubstituted (C6-C60) heteroaryl;
    Ar 2 는 (C1-C60)알킬, (C3-C60)시클로알킬, N, O, S, Si 및 P로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C7-C60)바이시클로알킬, 아다만틸, (C2-C60)알케닐, (C2-C60)알키닐, (C6-C60)아릴 및 (C3-C60)헤테로아릴로부터 선택되며; Ar 2 is (C1-C60) alkyl, (C3-C60) cycloalkyl, N, O, S, Si, and the 5-6 membered containing one or more selected from P heterocycloalkyl, (C7-C60) bicycloalkyl roal Kiel, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl is selected from;
    Ar 3 은 서로 독립적으로 수소, (C1-C60)알킬, 할로겐, 시아노, (C3-C60)시클로알킬, N, O, S, Si 및 P로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C7-C60)바이시클로알킬, 아다만틸, (C2-C60)알케닐, (C2-C60)알키닐, (C6-C60)아릴, (C1-C60)알콕시, (C6-C60)아릴옥시, (C3-C60)헤테로아릴, (C6-C60)아릴티오, (C1-C60)알킬티오, 모노 또는 디(C1-C30)알킬아미노, 모노 또는 디(C6-C30)아릴아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, 모노 또는 디(C6-C30)아릴보라닐, 모노 또는 디(C1-C60)알킬보라닐, 나이트로 및 하이드록시로부터 선택되며; Ar 3 is independently hydrogen, (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, 5-6 membered containing N, O, S, at least one selected from Si and P to each other heterocycloalkyl, (C7-C60) alkyl, bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl, (C1-C60) alkoxy, (C6- C60) aryloxy, (C3-C60) heteroaryl, (C6-C60) arylthio, (C1-C60) alkylthio, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino , tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, mono or di (C6-C30) aryl boranyl, mono or di ( C1-C60) alkyl boranyl, is selected from nitro, and hydroxy;
    상기 Ar 1 내지 Ar 3 의 알킬, 시클로알킬, 헤테로시클로알킬, 바이시클로알킬, 아다만틸, 알케닐, 알키닐, 아릴, 알콕시, 아릴옥시, 헤테로아릴, 아릴티오, 알킬티오, 알킬아미노, 아릴아미노, 트리알킬실릴, 디알킬아릴실릴, 트리아릴실릴, 아릴보라닐 또는 알킬보라닐은 (C1-C60)알킬, 할로겐, 시아노, (C3-C60)시클로알킬, N, O, S, Si 및 P로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C7-C60)바이시클로알킬, 아다만틸, (C2-C60)알케닐, (C2-C60)알키닐, (C6-C60)아릴, (C1-C60)알콕시, (C6-C60)아릴옥시, P(=O)R a R b [R a 및 R b 는 서로 독립적으로 (C1-C60)알킬 또는 (C6-C60)아릴]로 치환된 (C6-C60)아릴, (C3-C60)헤테로아릴, (C6-C60)아릴로 치환된 (C3-C60)헤테로아릴, (C1-C60)알킬로 치환된 (C3-C60)헤테로아릴, (C6-C60)아르(C1-C60)알킬, (C6-C60)아릴티오, (C1-C60)알킬티오, 모 Of said Ar 1 to Ar 3 alkyl, cycloalkyl, heterocycloalkyl, alkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, aryloxy, heteroaryl, arylthio, alkylthio, alkylamino, aryl amino, trialkylsilyl, dialkyl aryl silyl, triarylsilyl, aryl boranyl or alkyl boranyl is (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, N, O, S, Si and 5-6 membered heterocycloalkyl of containing one or more selected from P, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6 -C60) aryl, (C1-C60) alkoxy, (C6-C60) aryloxy, P (= O) R a R b [R a and R b are independently (C1-C60) alkyl or (C6-C60 to each other ) aryl] as a substituted (C6-C60) aryl, (C3-C60) heteroaryl, (C6-C60) aryl (C3-C60) heteroaryl, (C1-C60) a (C3- alkyl substituted by a substituted C60) heteroaryl, (C6-C60) ar (C1-C60) alkyl, (C6-C60) arylthio, (C1-C60) alkylthio, Mo 또는 디(C1-C30)알킬아미노, 모노 또는 디(C6-C30)아릴아미노, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, 모노 또는 디(C6-C30)아릴보라닐, 모노 또는 디(C1-C60)알킬보라닐, 나이트로 및 하이드록시로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있으며; Or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30 ) arylsilyl, mono or di (C6-C30) aryl boranyl, mono- or di (C1-C60) alkyl boranyl, may further be substituted by one or more substituents selected from the group consisting of nitro, and hydroxy, and;
    단, X 및 Y가 모두 N(Ar 1 )이고, Z 1 내지 Z 8 이 모두 C(Ar 3 )인 경우는 제외한다.] However, in the case where X and Y are both N (Ar 1) a, Z 1 to Z 8 are both C (Ar 3) is excluded.]
  2. 하기 화합물로부터 선택되는 유기 발광 화합물. The organic light emitting compound selected from the following compounds.
    Figure 112014111295299-pat00040
    Figure 112014111295299-pat00041
    [상기 Ar 1 은 치환 또는 비치환된 (C6-C60)헤테로아릴로 치환된 (C6-C60)아릴, 또는 치환 또는 비치환된 (C6-C60)헤테로아릴이고; [Wherein Ar 1 is substituted or unsubstituted (C6-C60) substituted with a heteroaryl (C6-C60) aryl, or a substituted or unsubstituted (C6-C60) heteroaryl;
    Ar 2 는 (C1-C60)알킬, (C3-C60)시클로알킬, N, O, S, Si 및 P로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 헤테로시클로알킬, (C7-C60)바이시클로알킬, 아다만틸, (C2-C60)알케닐, (C2-C60)알키닐, (C6-C60)아릴 및 (C3-C60)헤테로아릴로부터 선택된다.] Ar 2 is (C1-C60) alkyl, (C3-C60) cycloalkyl, N, O, S, Si, and the 5-6 membered containing one or more selected from P heterocycloalkyl, (C7-C60) bicycloalkyl roal Kiel, Ah is chosen from adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl and (C3-C60) heteroaryl group.]
  3. 제1항에 있어서, According to claim 1,
    하기 화합물로부터 선택되는 유기 발광 화합물. The organic light emitting compound selected from the following compounds.
    Figure 112014025783015-pat00042
    Figure 112014025783015-pat00043
    [상기 Ar 1 및 Ar 2 는 상기 청구항 제1항에서의 정의와 동일하다.] [Wherein Ar 1 and Ar 2 is as defined in claim 1, wherein said claims.]
  4. 제1항에 있어서, According to claim 1,
    하기 화합물로부터 선택되는 유기 발광 화합물. The organic light emitting compound selected from the following compounds.
    Figure 112014025783015-pat00044
    [상기 Ar 1 는 상기 청구항 제1항에서의 정의와 동일하다.] [Wherein Ar 1 is as defined in claim 1, wherein said claims.]
  5. 제1항 내지 제4항 중의 어느 한 항에 따른 유기 발광 화합물을 포함하는 유기 전계 발광 소자. The organic electroluminescent device comprising an organic electroluminescent compound according to any one of claims 1 to 4.
  6. 제5항에 있어서, 6. The method of claim 5,
    상기 유기 전계 발광 소자는 제1전극; The organic electroluminescent device comprising: a first electrode; 제2전극; A second electrode; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어져 있으며, 상기 유기물층은 상기 유기 발광 화합물 하나 이상과 인광 도판트 하나 이상을 포함하는 유기 전계 발광 소자. And the second layer consists of at least one organic layer interposed between the first electrode and the second electrode, the organic layer is an organic electroluminescent device including the organic light emitting compound and at least one phosphorescent dopant is at least one.
  7. 제6항에 있어서, 7. The method of claim 6,
    상기 유기물층에 아릴아민계 화합물 및 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물을 더 포함하는 유기 전계 발광 소자. The organic layer aryl amine compounds and styryl aryl organic electroluminescent device further comprises an amine compound amine compound selected from the group consisting of the above.
  8. 제6항에 있어서, 7. The method of claim 6,
    상기 유기물층에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열 금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함하는 유기 전계 발광 소자. Group 1, Group 2 on the organic layer, 4-cycle, the organic electroluminescent device further comprises a 5 period transition metals, lanthanide metals and one or more metal or complex compound is selected from the group consisting of organic metals of d- transition element.
  9. 제6항에 있어서, 7. The method of claim 6,
    상기 유기물층은 발광층 및 전하생성층을 포함하는 유기 전계 발광 소자. The organic layer is an organic light emitting device comprising: a light emitting layer and the charge generating layer.
  10. 제6항에 있어서, 7. The method of claim 6,
    상기 유기물층에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자. A white light emitting organic electroluminescent device using the organic material layer comprises at least one organic light-emitting layer to the blue, red or green light emission at the same time.
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