KR20100137188A - 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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KR20100137188A
KR20100137188A KR1020090055483A KR20090055483A KR20100137188A KR 20100137188 A KR20100137188 A KR 20100137188A KR 1020090055483 A KR1020090055483 A KR 1020090055483A KR 20090055483 A KR20090055483 A KR 20090055483A KR 20100137188 A KR20100137188 A KR 20100137188A
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substituted
unsubstituted
aryl
alkyl
compound
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김치식
조영준
권혁주
김봉옥
김성민
윤승수
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다우어드밴스드디스플레이머티리얼 유한회사
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Priority to KR1020090055483A priority Critical patent/KR20100137188A/en
Priority to PCT/KR2010/003965 priority patent/WO2010151011A1/en
Priority to TW099120051A priority patent/TW201109420A/en
Publication of KR20100137188A publication Critical patent/KR20100137188A/en

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Abstract

PURPOSE: A novel organic electroluminescent compound and an organic electroluminescent device employing the same are provided to ensure excellent light emitting efficiency and lifetime of devices and proper color coordinate. CONSTITUTION: A novel organic electroluminescent compound is represented by chemical formula 1. In chemical formula 1, R1 ~ R5 are hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C30) aryl bonded with substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) heteroaryl, heterocycloalkyl of substituted or unsubstituted 5-7-membered heterocycloalkyl, 5-7-membered heterocycloalky bonded with one or more substituted or unsubstituted aromatic rings, substituted or unsubstituted (C3-C30) cycloalkyl, NR11R12, BR13R14, PR15R16, P(=O)R17R18, and RaRbRcSi-.

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 소자 에 관한 것으로, 상세하게는 본 발명에 따른 유기 발광 화합물은 하기 화학식 1로 표시되는 것을 특징으로 한다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, in detail, the organic light emitting compound according to the invention is characterized in that represented by the formula (1).

[화학식 1][Formula 1]

Figure 112009037622889-PAT00002
Figure 112009037622889-PAT00002

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

유기 EL 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 when an electron is injected into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) and then disappears after pairing electrons and holes. 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.

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

유기EL소자는 보통 anode/HIL/HTL/EML/ETL/EIL/cathode로 구성되는데 발광층(EML)을 어떻게 형성하느냐에 따라 청색, 녹색, 적색의 유기 전기 발광 소자를 각각 구현할 수가 있다. The organic EL device is usually composed of anode / HIL / HTL / EML / ETL / EIL / cathode. The organic electroluminescent device of blue, green, and red can be realized depending on how the emission layer (EML) is formed.

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 유기 EL 소자의 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 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 EL devices has emerged as an urgent task, and considering the level of EL characteristics required in medium and large OLED panels, it is urgent to develop materials that are much superior to existing light emitting materials.

한편, 녹색 형광 재료로는 Alq를 호스트로 하여, 도판트로는 쿠마린 유도체(화합물 d, C545T), 퀴나크리돈 유도체(화합물 e), DPT(화합물 f) 등을 수 내지 십수 % 정도로 도핑을 하는 시스템이 개발되어 널리 쓰이고 있다. 그러나, 이들 종래의 발광재료는 초기 발광효율의 경우, 상용화 가능한 수준의 성능을 보이나, 초기 효율 저하가 두드러지며 수명 측면에서 상당한 문제점을 보이고 있어, 대화면의 고성능 패널에서는 채택하기가 힘든 한계를 보이고 있다.On the other hand, as a green fluorescent material, Alq is used as a host, and as a dopant, doping coumarin derivatives (compounds d and C545T), quinacridone derivatives (compound e), DPT (compound f) and the like are about 10 to 10%. It is developed and widely used. However, these conventional light emitting materials show a commercially available level of performance in the case of the initial luminous efficiency, but the initial efficiency decreases remarkably and shows considerable problems in terms of lifespan. .

Figure 112009037622889-PAT00003
Figure 112009037622889-PAT00003

또한, OLED 소자에서의 수명 측면에서도 결코 만족할만한 수준이 되질 못하여 더욱 안정되고, 더욱 성능이 뛰어난 호스트 재료의 개발이 요구되고 있다.In addition, in terms of lifespan in OLED devices, they are never satisfactory, and development of a more stable and more excellent host material is required.

따라서 본 발명의 목적은 첫째로, 상기한 문제점들을 해결하기 위하여 기존의 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며 둘째로, 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide an organic light emitting compound having excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems, and secondly, to solve the above organic light emitting compound. It is to provide a high efficiency and long life organic electroluminescent element employed as a light emitting 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 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by the following formula (1) and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has good luminous efficiency and excellent life characteristics of the material OLED excellent in driving life of the device There is an advantage to manufacture the device.

[화학식 1][Formula 1]

Figure 112009037622889-PAT00004
Figure 112009037622889-PAT00004

[상기 화학식 1에서, [In Formula 1,

R1 내지 R5는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 (C3-C30)시 클로알킬이 하나이상 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, NR11R12, BR13R14, PR15R16, P(=O)R17R18[R11 내지 R18은 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이다.], RaRbRcSi-[Ra,Rb 및 Rc는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬 또는 치환 또는 비치환된(C6-C30)아릴이다.], 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, RdY-[Y는 S 또는 O이고, Rd는 치환 또는 비치환된(C1-C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이다.] 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐,

Figure 112009037622889-PAT00005
또는
Figure 112009037622889-PAT00006
이고, 단 R4과 R5는 동시에 수소 또는 중수소는 아니고;R 1 to R 5 are independently of each other Substituted or fused with hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl, or One or more unfused (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring (C3-C30) cycloalkyl, cyano, NR 11 R 12 , BR 13 R 14 , PR 15 R 16 , P (= O) R 17 R 18 [R 11 to R 18 are independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6- C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl.], R a R b R c Si- [R a , R b and R c are each independently substituted or unsubstituted (C1-C30 Alkyl or substitution or Substituted (C6-C30) aryl], a substituted or unsubstituted (C6-C30) aralkyl (C1-C30) alkyl, R d Y- [Y is S or O, R d is a substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl.] Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,
Figure 112009037622889-PAT00005
or
Figure 112009037622889-PAT00006
Provided that R 4 and R 5 are not simultaneously hydrogen or deuterium;

W, X, Y 및 Z는 서로 독립적으로 -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Si(R34)(R35)-, -P(R36)-, -P(=O)(R37)-, -C(=O)- 또는 -B(R38)-이고;W, X, Y and Z are independently of each other-(CR 31 R 32 ) m -,-(R 31 ) C = C (R 32 )-, -N (R 33 )-, -S-, -O- , -Si (R 34 ) (R 35 )-, -P (R 36 )-, -P (= 0) (R 37 )-, -C (= 0)-, or -B (R 38 )-;

R21 내지 R23 및 R31 내지 R38은 상기 R1 내지 R3에서의 정의와 동일하며, 상기 R31 내지 R38은 각각 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;R 21 to R 23 and R 31 to R 38 are the same as defined above for R 1 to R 3 , wherein R 31 to R 38 each represent (C 3 -C 30) alkyl with or without adjacent substituents and fused rings Ethylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고; The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P;

m은 0, 1 또는 2의 정수이다.]m is an integer of 0, 1 or 2.]

본 발명에 기재된 “알킬”, “알콕시” 및 그 외 “알킬”부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다. 본 발명에 기재된 “시클로알킬”은 단일 고리계 뿐만 아니라 아다만틸 또는 바이시클로알킬과 같은 여러 고리계 탄화수소도 포함한다.Substituents comprising the "alkyl", "alkoxy" and other "alkyl" moieties described herein include both straight and pulverized forms. The "cycloalkyl" described in the present invention includes not only a single ring system but also various ring hydrocarbons such as adamantyl or bicycloalkyl.

본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 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 6원 단환 헤테로아릴, 및 하나 이상의 벤젠 환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연걸된 형태도 포함한다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 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 a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthasenyl, fluoranthenyl, and the like. It is not limited to this. 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. The "heteroaryl" described in the present invention contains 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. Meaning an aryl group which is 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, the heteroaryl in the present invention also includes a form in which one or more heteroaryls are linked by a single 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 include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetra Monocyclic heteroaryl such as zolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothia Zolyl, Benzoisoxazolyl, Benzoxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cinolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Phenantridinyl , Polycyclic heteroaryls such as benzodioxolyl and the like, and their corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like. .

또한, 본 발명에 기재되어 있는 “(C1-C30)알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬옥시, (C1-C30)알킬티오” 등의 알킬은 탄소수 1 내지 20개로 제한될 수 있고, 탄소수 1 내지 10개로 제한될 수 있다. “(C6-C30)아릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C6-C30)아릴옥시, (C6-C30)아릴티오”등의 아릴은 탄소수 6 내지 20개로 제한될 수 있고, 탄소수 6 내지 12개로 제한될 수 있다. “(C3-C30)헤테로아릴”의 헤테로아릴은 탄소수 4 내지 20개로 제한될 수 있고, 탄소수 4 내지 12개로 제한될 수 있다. “(C3-C30)시클로알킬”의 시클로알킬은 탄소수 3 내지 20개로 제한될 수 있고, 탄소수 3 내지 7개로 제한될 수 있다. “(C2-C30)알케닐 또는 알키닐”의 알케닐 또는 알키닐은 탄소수 2 내지 20개로 제한될 수 있고, 탄소수 2 내지 10개로 제한될 수 있다.Also described herein are “(C1-C30) alkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C6-C30) ar (C1-C30) Alkyl, such as) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio ”, etc., may be limited to 1 to 20 carbon atoms, and may be limited to 1 to 10 carbon atoms. “(C6-C30) aryl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) ar (C1-C30) alkyl, (C6-C30) Aryl, such as aryloxy, (C6-C30) arylthio ", may be limited to 6 to 20 carbon atoms, and may be limited to 6 to 12 carbon atoms. Heteroaryl of "(C3-C30) heteroaryl" may be limited to 4 to 20 carbon atoms, it may be limited to 4 to 12 carbon atoms. The cycloalkyl of "(C3-C30) cycloalkyl" may be limited to 3 to 20 carbon atoms, and may be limited to 3 to 7 carbon atoms. Alkenyl or alkynyl of "(C2-C30) alkenyl or alkynyl" may be limited to 2 to 20 carbon atoms, and may be limited to 2 to 10 carbon atoms.

또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재는 상기 R1 내지 R5 및 R11 내지 R18의 치환기가 각각 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된 (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C6-C30)시클로알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, 아다만틸, (C7-C30)바이시클로알킬, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NR41R42, BR43R44, PR45R46, P(=O)R47R48[R41 내지 R48은 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이다.], (C6-C30)아 르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성하는 것을 의미한다.In addition, the description of "substituted or unsubstituted" described in the present invention is that the substituents of R 1 to R 5 and R 11 to R 18 are each independently deuterium, halogen, halogen substituted or unsubstituted (C1-C30) (C3-C30) heteroaryl substituted or unsubstituted with alkyl, (C6-C30) aryl, (C6-C30) aryl, 5- to 7-membered heterocycloalkyl, 5- to 7 fused with one or more aromatic rings Original heterocycloalkyl, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl fused with one or more aromatic rings, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) Arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7-C30) bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR 41 R 42 , BR 43 R 44 , PR 45 R 46 , P (= O) R 47 R 48 [R 41 to R 48 are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6 -C30) aryl or substituted or unsubstituted (C3-C30) hete Aryl], (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6 -C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, (C6-C30) aryloxycarbonyl , (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nitro or hydroxy It is further substituted with one or more selected from the group consisting of, or means that adjacent substituents are connected to form a ring.

상기 R1 내지 R3는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 아다만틸, NR11R12[R11 및 R12은 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이다.] 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이다.]이고; R4 및 R5는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 (C3-C30)시클로알킬이 하나이상 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, 또는 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬로부터 선택된다.R 1 to R 3 are independently of each other Hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted (C3 -C30) cycloalkyl, substituted or unsubstituted adamantyl, NR 11 R 12 [R 11 and R 12 are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30 Aryl or substituted or unsubstituted (C3-C30) heteroaryl] or R a R b R c Si- [R a , R b and R c are independently substituted or unsubstituted (C1-C30) Alkyl or substituted or unsubstituted (C6-C30) aryl. R 4 and R 5 are each independently substituted with one or more substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl One or more substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring Fused 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted aromatic ring is selected from one or more fused (C3-C30) cycloalkyl.

상기 R1 내지 R3는 서로 독립적으로 수소, 중수소, 할로겐, 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 에틸헥실, 헵틸, 옥틸 등의 알킬, 페닐, 나프틸, 플루오레닐, 바이페닐, 페난트릴, 터페닐, 피레닐, 퍼릴레닐, 스피로바이플루오레닐, 플루오란테닐, 크리세닐, 트리페닐레닐 등의 아릴, 디벤조티오페닐, 디벤조퓨릴, 카바졸릴, 피리딜, 퓨릴, 티에닐, 퀴놀릴, 트리아지닐, 피리미디닐, 피리다지닐, 퀴녹살리닐, 페난트롤리닐 등의 헤테로아릴, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실 등의 시클로알킬, 아다만틸, 모노 또는 디-페닐아미노, 모노 또는 디-메틸아미노, 모노 또는 디-피리딜아미노 등의 아미노, 트리메틸실릴, 트리에틸실릴, 디메틸에틸실릴, 트리부틸실릴 등의 트리알킬실릴, 디메틸페닐실릴 등의 디알킬아릴실릴 또는 트리페닐실릴, 트리나프틸실릴 등의 트리아릴실릴로부터 선택되어지나, 이에 한정되는 것은 아니며, 상기 화학식 1에서와 같이 치환되거나 비치환될 수 있다.R 1 to R 3 are independently of each other hydrogen, deuterium, halogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, alkyl, phenyl, naphthyl, fluorenyl, biphenyl, Aryl, dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, such as phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthhenyl, chrysenyl, triphenylenyl, Heteroaryl such as thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, mono Or dialkyls such as amino such as di-phenylamino, mono or di-methylamino, mono or di-pyridylamino, trialkylsilyls such as trimethylsilyl, triethylsilyl, dimethylethylsilyl and tributylsilyl, and dimethylphenylsilyl Alkylarylsilyl or triphenylsilyl, Triarylsilyl such as trinaphthylsilyl may be selected from, but is not limited thereto, and may be substituted or unsubstituted as in Chemical Formula 1.

상기 R4 및 R5는 서로 독립적으로 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 에틸헥실, 헵틸, 옥틸 등의 알킬, 페닐, 나프틸, 플루오레닐, 바이페닐, 페난트릴, 터페닐, 피레닐, 퍼릴레닐, 스피로바이플루오레닐, 플루오란테닐, 크리세닐, 트리페닐레닐 등의 아릴, 1,2-디하이드로아세나프틸 등의 시클로알킬이 하나 이상 융합된 아릴, 디벤조티에닐, 디벤조퓨릴, 카바졸릴, 피리딜, 퓨릴, 티에닐, 퀴놀릴, 트리아지닐, 피리미디닐, 피리다지닐, 퀴녹살리닐, 페난트롤리닐 등의 헤테로아릴, 모폴리닐, 티오모폴리닐, 모폴리노, 티오모폴리노, 피페리디닐, 피페리디노 등의 헤테로시클로알킬, 벤조피페리디노, 벤조피롤리디노 등의 방향족고리가 하나 이상 융합된 5원 내지 7원의 헤테로시클로알킬, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 시클로헵틸, 시클로옥틸 등의 시클로알킬, 벤조시클로헥실 등의 방향족고리가 하나이상 융합된 시클로알킬, 아다만틸 또는 바이시클로[2.2.1]헵틸 등의 바이시클로알킬로부터 선택되어지나, 이에 한정되는 것은 아니며, 상기 화학식 1에서와 같이 치환되거나 비치환될 수 있다.R 4 and R 5 are independently of each other methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, alkyl, phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, Aryl, dibenzothier, in which at least one cycloalkyl such as aryl such as pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, and triphenylenyl is fused, and cycloalkyl such as 1,2-dihydroacenaphthyl Heteroaryl, morpholinyl, thiomorpholyl, such as nil, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl 5- to 7-membered heterocyclo fused with one or more aromatic rings such as heterocycloalkyl such as nil, morpholino, thiomorpholino, piperidinyl, and piperidino, and aromatic rings such as benzopiperidino and benzopyrrolidino Alkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, Aromatic rings, such as cycloalkyl, such as cyclooctyl, and benzocyclohexyl, are selected from bicycloalkyl, such as cycloalkyl, adamantyl, or bicyclo [2.2.1] heptyl, which are fused, but are not limited thereto. It may be substituted or unsubstituted as in Chemical Formula 1.

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 112009037622889-PAT00007
Figure 112009037622889-PAT00007

Figure 112009037622889-PAT00008
Figure 112009037622889-PAT00008

Figure 112009037622889-PAT00009
Figure 112009037622889-PAT00009

Figure 112009037622889-PAT00010
Figure 112009037622889-PAT00010

Figure 112009037622889-PAT00011
Figure 112009037622889-PAT00011

Figure 112009037622889-PAT00012
Figure 112009037622889-PAT00012

Figure 112009037622889-PAT00013
Figure 112009037622889-PAT00013

Figure 112009037622889-PAT00014
Figure 112009037622889-PAT00014

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 112009037622889-PAT00015
Figure 112009037622889-PAT00015

[상기 반응식 1에서 X, Y, Z 및 R1 내지 R5는 상기 화학식 1에서의 정의와 동일하다.][X, Y, Z and R 1 to R 5 in Scheme 1 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 1 또는 2의 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 2 또는 3으로 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 or 2 above. 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 compounds represented by the following Chemical Formulas 2 or 3.

[화학식 2][Formula 2]

[화학식 3](3)

Figure 112009037622889-PAT00017
Figure 112009037622889-PAT00017

[상기 화학식 3에서, Ar11 및 Ar12는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C4-C30)헤테로아릴, 치환 또는 비치환된 (C6-C30)아릴아미노, (C1-C30)알킬아미노, 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)시클로알킬이고, Ar11 및 Ar12는 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하고; [In Formula 3, Ar 11 and Ar 12 are independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C4-C30) hetero One or more fused aryl, substituted or unsubstituted (C6-C30) arylamino, (C1-C30) alkylamino, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic rings 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring is a (C3-C30) cycloalkyl fused with one or more, Ar 11 and Ar 12 are Linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

c가 1인 경우 Ar13은 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C4-C30)헤테로아릴 또는 하기 구조에서 선택되는 치환기이고;when c is 1 Ar 13 is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C4-C30) heteroaryl or a substituent selected from the following structures;

Figure 112009037622889-PAT00018
Figure 112009037622889-PAT00018

c가 2인 경우 Ar13는 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된(C4-C30)헤테로아릴렌 또는 하기 구조에서 선택되는 치환기이고;when c is 2, Ar 13 is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C4-C30) heteroarylene or a substituent selected from the following structures;

Figure 112009037622889-PAT00019
Figure 112009037622889-PAT00019

Ar14 및 Ar15은 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴렌 또는 치환 또는 비치환된(C4-C30)헤테로아릴렌이고;Ar 14 and Ar 15 are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C4-C30) heteroarylene;

R101 내지 R103는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬 또는 치환 또는 비치환된(C6-C30)아릴이고;R 101 to R 103 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl;

d는 1 내지 4의 정수이며, e는 0 또는 1의 정수이다.]d is an integer of 1 to 4, and e is an integer of 0 or 1.]

상기 화학식 2 또는 3의 도판트 화합물은 하기 구조의 화합물로 예시될 수 있으나, 이에 한정되는 것은 아니다. The dopant compound of Formula 2 or 3 may be exemplified as a compound having the following structure, but is not limited thereto.

Figure 112009037622889-PAT00020
Figure 112009037622889-PAT00020

Figure 112009037622889-PAT00021
Figure 112009037622889-PAT00021

Figure 112009037622889-PAT00022
Figure 112009037622889-PAT00022

본 발명의 유기 전계 발광 소자에 있어서, 화학식 1의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. 상기 아릴아민계 화합물 또는 스티릴아릴아민계 화합물은 출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In the organic electroluminescent device of the present invention, it may include one or more compounds selected from the group consisting of an organic light emitting compound of formula (1) and at the same time an arylamine compound or styrylarylamine compound. The arylamine-based compound or styrylarylamine-based compound is exemplified in Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but is not limited thereto.

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 출원번호 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 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 할 로겐화 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, at least one inner surface of a pair of electrodes is selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer (hereinafter, these are referred to as "surface layers"). It is preferable to arrange | position the above. Specifically, a chalcogenide (containing oxide) layer of a metal of silicon and aluminum is disposed on the anode surface of the light emitting medium layer side, and a halogenated metal layer or metal oxide layer is disposed on the cathode surface of the light emitting medium layer side. It is preferable. As a result, drive stabilization 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 발광화합물은 발광효율이 좋고 재료의 수명특성이 뛰어 나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다.The organic light emitting compound according to the present invention has an advantage of producing an OLED device having excellent 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 3의 제조Preparation Example 1 Preparation of Compound 3

Figure 112009037622889-PAT00023
Figure 112009037622889-PAT00023

화합물 compound 1-11-1 의 제조Manufacture

2-(메톡시카보닐)페닐보론산 10 g(55.55 mmol), 1,3,5-트리브로모벤젠 19.2 g(61.12 mmol), Pd(PPh3)4 1.9 g(0.03 mmol), 2M K2CO3 수용액 80 ml, 톨루엔 200 ml 및 에탄올 50 ml을 넣고 환류 교반시켰다. 5시간 후 상온으로 냉각하고 증류수를 넣었다. EA로 추출하고 무수 MgSO4로 건조하였다. 감압 증류하고 컬럼으로 분리하여 화합물 1-1 13.5 g(36.38 mmol, 65.73 %)을 얻었다. 10 g (55.55 mmol) of 2- (methoxycarbonyl) phenylboronic acid, 19.2 g (61.12 mmol) of 1,3,5-tribromobenzene, Pd (PPh 3 ) 4 1.9 g (0.03 mmol), 2M K 80 ml of 2 CO 3 aqueous solution, 200 ml of toluene and 50 ml of ethanol were added thereto, and the mixture was stirred under reflux. After 5 hours, cooled to room temperature and distilled water was added. Extracted with EA and dried over anhydrous MgSO 4 . Distillation under reduced pressure and separation by column afforded 13.5 g (36.38 mmol, 65.73%) of compound 1-1 .

화합물 compound 1-21-2 의 제조Manufacture

화합물 1-1 13.5 g(36.38 mmol)을 THF 300 ml에 녹이고 메틸마그네슘 브로마이드 36.48 ml(109.44 mmol, 3.0M in diethyl ether)을 천천히 첨가하고, 60℃로 교반하였다. 10시간 후 상온으로 냉각하고 증류수를 천천히 가하고, EA로 추출하고 무수 MgSO4로 건조하였다. 감압 증류하고 컬럼 분리하여 화합물 1-2 12 g(32.42 mmol, 90.07 %)을 얻었다.13.5 g (36.38 mmol) of Compound 1-1 were dissolved in 300 ml of THF, and 36.48 ml (109.44 mmol, 3.0 M in diethyl ether) of methylmagnesium bromide were slowly added thereto, followed by stirring at 60 ° C. After 10 hours, the mixture was cooled to room temperature, distilled water was slowly added, extracted with EA, and dried over anhydrous MgSO 4 . Distillation under reduced pressure and column separation yielded 12 g (32.42 mmol, 90.07%) of compound 1-2 .

화합물 compound 1-31-3 의 제조Manufacture

화합물 1-2 12 g(32.42 mmol)을 아세트산 200 ml 및 H3PO4 300 ml과 섞고 120℃로 교반시켰다. 12시간 후 상온으로 냉각하고 증류수를 가하고, EA로 추출하고 무수 MgSO4로 건조하였다. 감압 증류후 컬럼으로 분리하여 화합물 1-3 9 g(25.56 mmol, 78.85 %)을 얻었다. 12 g (32.42 mmol) of Compound 1-2 were mixed with 200 ml of acetic acid and 300 ml of H 3 PO 4 and stirred at 120 ° C. After 12 hours, the mixture was cooled to room temperature, distilled water was added, extracted with EA, and dried over anhydrous MgSO 4 . Distillation under reduced pressure followed by column separation yielded Compound 1-3 (9 g, 25.56 mmol, 78.85%).

화합물 compound 1-41-4 의 제조Manufacture

화합물 1-3 9 g(25.56 mmol)을 MC 100 ml에 녹이고 AlCl3 5.11 g(38.34 mmol) 및 무수프탈산 3.7 g(25.56 mmol)을 넣은 후 40℃로 12시간동안 교반시켰다. 상온으로 냉각하고 증류수를 넣었다. MC로 추출하고 염산 수용액으로 씻어 주었다. 무수 MgSO4로 건조하고 감압 증류하고 컬럼 분리하여 화합물 1-4 12 g(23.99 mmol, 93.86 %)을 얻었다. 9 g (25.56 mmol) of Compound 1-3 was dissolved in 100 ml of MC, and 5.11 g (38.34 mmol) of AlCl 3 and 3.7 g (25.56 mmol) of phthalic anhydride were added thereto, followed by stirring at 40 ° C. for 12 hours. Cooled to room temperature and distilled water was added. Extracted with MC and washed with an aqueous hydrochloric acid solution. Drying over anhydrous MgSO 4 , distillation under reduced pressure, and column separation yielded Compound 1-4 12 g (23.99 mmol, 93.86%).

화합물 compound 1-51-5 의 제조Manufacture

화합물 1-4 12 g(23.99 mmol)을 아세트산 50 ml 및 황산 50 ml와 섞고 100℃로 교반하였다. 5시간 후 상온으로 냉각하고 증류수를 넣었다. NaOH수용액으로 중성을 만들고 MC로 추출하였다. 무수 MgSO4로 건조하고 감압 증류하였다. 컬럼 분리 하여 화합물 1-5 3.6 g(7.46 mmol, 31.12 %)을 얻었다. 12 g (23.99 mmol) of Compound 1-4 were mixed with 50 ml of acetic acid and 50 ml of sulfuric acid and stirred at 100 ° C. After 5 hours, cooled to room temperature and distilled water was added. Neutralized with NaOH aqueous solution and extracted with MC. It was dried over anhydrous MgSO 4 and distilled under reduced pressure. 3.6 g (7.46 mmol, 31.12%) of Compound 1-5 was obtained by column separation.

화합물 compound 1-61-6 의 제조Manufacture

2-(메톡시카보닐)페닐보론산 3.35 g(18.66 mmol), 화합물 1-5 3.6 g(7.46 mmol), Pd(PPh3)4 0.43 g(0.37 mmol), 2M K2CO3 수용액 11 ml, 톨루엔 50 ml 및 에탄올 25 ml을 넣고 환류 교반시켰다. 10시간 후 상온으로 냉각하고 증류수를 넣었다. EA로 추출하고 무수 MgSO4로 건조하였다. 감압 증류하고 컬럼으로 분리하여 화합물 1-6 4 g(6.74 mmol, 90.4 7%)을 얻었다.3.35 g (18.66 mmol) of 2- (methoxycarbonyl) phenylboronic acid, 3.6 g (7.46 mmol) of compound 1-5 , Pd (PPh 3 ) 4 0.43 g (0.37 mmol), 11 ml of 2M K 2 CO 3 aqueous solution 50 ml of toluene and 25 ml of ethanol were added and stirred under reflux. After 10 hours, cooled to room temperature and distilled water was added. Extracted with EA and dried over anhydrous MgSO 4 . Distillation under reduced pressure and column separation yielded Compound 1-6 4 g (6.74 mmol, 90.4 7%).

화합물 compound 1-71-7 의 제조Manufacture

화합물 1-6 4 g(6.74 mmol)을 THF 100 ml에 녹이고 메틸마그네슘 브로마이드 13.49 ml(40.49 mmol, 3.0M in diethyl ether)을 천천히 가하고, 60℃로 교반하였다. 10시간 후 상온으로 냉각하고 증류수를 천천히 가하고 EA로 추출하고 무수 MgSO4로 건조하였다. 감압 증류하고 컬럼 분리하여 화합물 1-7 3.2 g(5.39 mmol, 80.11 %)을 얻었다.4 g (6.74 mmol) of Compound 1-6 were dissolved in 100 ml of THF, and 13.49 ml (40.49 mmol, 3.0 M in diethyl ether) of methylmagnesium bromide were slowly added thereto, followed by stirring at 60 ° C. After 10 hours, the mixture was cooled to room temperature, distilled water was added slowly, extracted with EA, and dried over anhydrous MgSO 4 . Distillation under reduced pressure and column separation yielded 3.2 g (5.39 mmol, 80.11%) of compound 1-7 .

화합물 compound 1-81-8 의 제조Manufacture

화합물 1-7 3.2 g(5.39 mmol)을 아세트산 50 ml 및 H3PO4 50ml와 섞고 120℃로 교반하였다. 12시간 후 상온으로 냉각하고 증류수를 넣었다. EA로 추출하고 무수 MgSO4로 건조하였다. 감압 증류후 컬럼으로 분리하여 화합물 1-8 2.3 g(4.13 mmol, 76.65 %)을 얻었다. 3.2 g (5.39 mmol) of Compound 1-7 were mixed with 50 ml of acetic acid and 50 ml of H 3 PO 4 and stirred at 120 ° C. After 12 hours, the mixture was cooled to room temperature and distilled water was added. Extracted with EA and dried over anhydrous MgSO 4 . After distillation under reduced pressure, the residue was separated by a column to obtain 2.3 g (4.13 mmol, 76.65%) of compound 1-8 .

화합물compound 1-9 1-9 의 제조Manufacture

브로모벤젠 1.75 g(11.15 mmol)을 THF 40 ml에 넣고 -78℃에서 n-buLi 4.6 ml(11.56mmol, 2.5M in hexane)을 천천히 가하였다. 한시간 후 화합물 1-8 2.3 g(4.13 mmol)을 첨가하였다. 온도를 천천히 상온으로 올리고 10시간 후 증류수를 넣고 EA로 추출하였다. 무수 MgSO4로 건조하고 감압 증류하였다. 정제하지 않고, 바로 다음 반응에 사용하였다. 1.75 g (11.15 mmol) of bromobenzene was added to 40 ml of THF, and 4.6 ml (11.56 mmol, 2.5 M in hexane) of n-buLi were slowly added at -78 ° C. After one hour 2.3 g (4.13 mmol) of compound 1-8 were added. The temperature was slowly raised to room temperature and after 10 hours, distilled water was added and extracted with EA. It was dried over anhydrous MgSO 4 and distilled under reduced pressure. Used directly in the next reaction without purification.

화합물 compound 33 의 제조Manufacture

조화합물 1-9 3.2 g을 KI 2.45 g(14.81 mmol), NaH2PO2H2O 3.13 g(29.62 mmol) 및 아세트산 50 ml와 섞고 120℃로 가열하였다. 14시간 후 상온으로 냉각하고 증류수를 넣었다. 생성된 고체를 감압 여과하고 NaOH수용액으로 씻어주었다. 컬럼 분리하여 화합물 3 1.6 g(2.35 mmol, 63.52 %)을 얻었다. 3.2 g of crude compound 1-9 were mixed with 2.45 g (14.81 mmol) of KI, 3.13 g (29.62 mmol) of NaH 2 PO 2 H 2 O and 50 ml of acetic acid and heated to 120 ° C. After 14 hours, cooled to room temperature and distilled water was added. The resulting solid was filtered under reduced pressure and washed with aqueous NaOH solution. Compound 3 1.6 g (2.35 mmol, 63.52%) was obtained by column separation.

[제조예 2]화합물 24의 제조Preparation Example 2 Preparation of Compound 24

Figure 112009037622889-PAT00024
Figure 112009037622889-PAT00024

화합물 compound 2-12-1 의 제조Manufacture

화합물 1-5 5 g(10.37 mmol)과 2-니트로페닐보론산 4.32 g(25.92 mmol)을 사용하는 것을 제외하고는 제조예 1에서 화합물 1-6과 동일한 방법으로 합성하여 화합물 2-1 4.7 g(8.29 mmol, 79.96 %)을 얻었다. Except for using 5 g (10.37 mmol) of Compound 1-5 and 4.32 g (25.92 mmol) of 2-nitrophenylboronic acid, Compound 2-1 4.7 g was synthesized in the same manner as in Compound 1-6. (8.29 mmol, 79.96%).

화합물 compound 2-22-2 의 제조Manufacture

화합물 2-1 4.7 g(8.29 mmol)을 트리에틸포스파이트 50 ml와 섞고 환류 교반하였다. 20시간 후 상온으로 냉각하고 감압 증류하였다. 컬럼 분리하여 화합물 2-2 2.5 g(4.97 mmol, 60.00 %)을 얻었다. 4.7 g (8.29 mmol) of Compound 2-1 were mixed with 50 ml of triethylphosphite and stirred under reflux. After 20 hours, the mixture was cooled to room temperature and distilled under reduced pressure. 2.5 g (4.97 mmol, 60.00%) of Compound 2-2 was obtained by column separation.

화합물 compound 2-32-3 의 제조Manufacture

화합물 2-2 2.5 g(4.97 mmol), 아이오도벤젠 2.21 ml(19.89 mmol), CuI 1.89 g(9.94 mmol), K2CO3 2.75 g(19.89 mmol) 및 1,2-디클로로벤젠 50 ml을 섞고 190℃로 가열하였다. 24시간 후 상온으로 냉각하고 유기 용매를 감압 증류하였다. 증류수를 넣고 EA로 추출하였다. 감압 증류하고 컬럼 분리하여 화합물 2-3 2.7 g(4.12 mmol, 82.97 %)을 얻었다. 2.5 g (4.97 mmol) of compound 2-2 , 2.21 ml (19.89 mmol) of iodobenzene, 1.89 g (9.94 mmol) of CuI, 2.75 g (19.89 mmol) of K 2 CO 3 and 50 ml of 1,2-dichlorobenzene were mixed Heated to 190 ° C. After 24 hours, the mixture was cooled to room temperature, and the organic solvent was distilled off under reduced pressure. Distilled water was added and extracted with EA. Distillation under reduced pressure and column separation yielded 2.7 g (4.12 mmol, 82.97%) of compound 2-3 .

화합물 compound 2-42-4 의 제조Manufacture

화합물 2-3 2.7 g(4.13 mmol)을 사용하는 것을 제외하고는 제조예 1에서 화합물 1-9과 동일한 방법으로 합성하였으며, 정제하지 않고, 바로 다음 반응에 사용하였다. Compound 2-3 was synthesized in the same manner as in the compound 1-9 in Preparation Example 1, except that 2.7 g (4.13 mmol) was used, and was used for the next reaction without purification.

화합물compound 24 24 의 제조Manufacture

조화합물 2-4 3.2 g을 사용하는 것을 제외하고는 제조예 1에서 화합물 3과 동일한 방법으로 합성하여 화합물 24 1.6 g(2.05 mmol, 49.98 %)을 얻었다. Except for using 3.2 g of crude compound 2-4, Compound 24 1.6 g (2.05 mmol, 49.98%) was obtained by the same method as Compound 3 in Preparation Example 1.

상기 제조예 1의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 31을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to 31 were prepared using the method of Preparation Example 1, and the 1 H NMR and the MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.

[표 1]TABLE 1

Figure 112009037622889-PAT00025
Figure 112009037622889-PAT00025

Figure 112009037622889-PAT00026
Figure 112009037622889-PAT00026

Figure 112009037622889-PAT00027
Figure 112009037622889-PAT00027

[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.An OLED device having a structure using the light emitting material of the present invention was produced.

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.First, a transparent electrode ITO thin film (15 Ω / □) obtained from an OLED glass (manufactured by Samsung Corning Corporation) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol. It was used after.

다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 4,4',4"-트리스(N,N-(2-나프틸)-페닐아미노)트리페닐아민(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-나프틸)-N,N'-디페닐-4,4'-디아민 (NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.Next, an ITO substrate is placed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine ( 2-TNATA), evacuated until the vacuum in the chamber reached 10 -6 torr, and applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N , N' -bis (α-naphthyl) -N , N' -diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition equipment, and the current was applied to the cell to give NPB. Was evaporated to deposit a 20 nm thick hole transport layer on the hole injection layer.

정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명에 따른 화합물 5를 넣고, 또 다른 셀에는 도판트로서 화합물 E을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 호스트를 기준으로 2 내지 5 중량%로 증착함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다.After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Compound 5 according to the present invention is added to one cell in a vacuum deposition apparatus as a host, and compound E is added as a dopant to another cell, and then the two materials are evaporated at different rates to 2 to 5% by weight based on the host. A 30 nm thick light emitting layer was deposited on the hole transport layer by deposition.

Figure 112009037622889-PAT00028
Figure 112009037622889-PAT00028

이어서 전자전달층으로써 트리스(8-히드록시퀴놀린)알루미늄(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 리튬퀴놀레이트 (Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다. Subsequently, tris (8-hydroxyquinoline) aluminum (III) (Alq) was deposited to a thickness of 20 nm as an electron transport layer, and then lithium quinolate (Liq) was deposited to a thickness of 1 to 2 nm using an electron injection layer. An OLED was fabricated by depositing an Al cathode to a thickness of 150 nm using another vacuum deposition equipment.

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.

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

진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 DNA 를 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that DNA was used instead of the compound of the present invention as a host material in one cell in a vacuum deposition apparatus.

Figure 112009037622889-PAT00029
Figure 112009037622889-PAT00029

상기 실시예 1 및 비교예 1에서 제조된 본 발명에 따른 유기 발광 화합물과 종래의 발광 화합물을 각각 함유하는 OLED 소자의 전력 효율을 각각 1,000 cd/m2에서 측정하여 하기 표 2에 나타내었다. To the above Example 1 and Comparative Example 1, respectively, measured at 1,000 cd / m 2 the power efficiency of an OLED device containing each of the organic light-emitting compound and a conventional electroluminescent compound according to the present invention in the manufacture shown in Table 2 below.

[표 2]TABLE 2

Figure 112009037622889-PAT00030
Figure 112009037622889-PAT00030

상기 표 2에 나타난 바와 같이, 본 발명의 재료를 녹색 발광 소자에 적용한 결과, 비교예 1 대비 동등이상의 색순도를 유지하면서 전력효율이 개선되었음을 확인할 수 있었다. As shown in Table 2, as a result of applying the material of the present invention to the green light emitting device, it was confirmed that the power efficiency was improved while maintaining the color purity equal to or greater than that of Comparative Example 1.

Claims (10)

하기 화학식 1로 표시되는 유기 발광 화합물.An organic light emitting compound represented by Formula 1 below. [화학식 1][Formula 1]
Figure 112009037622889-PAT00031
Figure 112009037622889-PAT00031
 [상기 화학식 1에서, [In Formula 1, R1 내지 R5는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 (C3-C30)시클로알킬이 하나이상 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, NR11R12, BR13R14, PR15R16, P(=O)R17R18[R11 내지 R18은 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이다.], RaRbRcSi-[Ra,Rb 및 Rc는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬 또는 치환 또는 비치환된(C6-C30)아릴이다.], 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, RdY-[Y는 S 또는 O이고, Rd는 치환 또는 비치환된(C1-C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이다.] 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐,
Figure 112009037622889-PAT00032
또는
Figure 112009037622889-PAT00033
이고, 단 R4과 R5는 동시에 수소 또는 중수소는 아니고;R 1 to R 5 are independently of each other Substituted or unsubstituted fused with one or more hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl Substituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring 5 1-7 membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring (C3-C30) cycloalkyl, cyano, NR 11 R 12 , BR 13 R 14 , PR 15 R 16 , P (= 0) R 17 R 18 [R 11 to R 18 are independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30). Aryl or substituted or unsubstituted (C3-C30) heteroaryl], R a R b R c Si- [R a , R b and R c are independently substituted or unsubstituted (C1-C30) Alkyl or substitution or Substituted (C6-C30) aryl], a substituted or unsubstituted (C6-C30) aralkyl (C1-C30) alkyl, R d Y- [Y is S or O, R d is a substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl.] Substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,
Figure 112009037622889-PAT00032
or
Figure 112009037622889-PAT00033
Provided that R 4 and R 5 are not simultaneously hydrogen or deuterium; W, X, Y 및 Z는 서로 독립적으로 -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Si(R34)(R35)-, -P(R36)-, -P(=O)(R37)-, -C(=O)- 또는 -B(R38)-이고;W, X, Y and Z are independently of each other-(CR 31 R 32 ) m -,-(R 31 ) C = C (R 32 )-, -N (R 33 )-, -S-, -O- , -Si (R 34 ) (R 35 )-, -P (R 36 )-, -P (= 0) (R 37 )-, -C (= 0)-, or -B (R 38 )-; R21 내지 R23 및 R31 내지 R38은 상기 R1 내지 R3에서의 정의와 동일하며, 상기 R31 내지 R38은 각각 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;R 21 to R 23 and R 31 to R 38 are the same as defined above for R 1 to R 3 , wherein R 31 to R 38 each represent (C 3 -C 30) alkyl with or without adjacent substituents and fused rings Ethylene or (C3-C30) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; 상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고; The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; m은 0, 1 또는 2의 정수이다.]m is an integer of 0, 1 or 2.] 제 1항에 있어서, The method of claim 1, 상기 R1 내지 R3는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 아다만틸, NR11R12[R11 및 R12은 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이다.] 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이다.]이고; R4 및 R5는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 (C3-C30)시클로알킬이 하나이상 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, 또는 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬인 것을 특징으로 하는 유기 발광 화합물.R 1 to R 3 are independently of each other Hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted (C3 -C30) cycloalkyl, substituted or unsubstituted adamantyl, NR 11 R 12 [R 11 and R 12 are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30 Aryl or substituted or unsubstituted (C3-C30) heteroaryl] or R a R b R c Si- [R a , R b and R c are independently substituted or unsubstituted (C1-C30) Alkyl or substituted or unsubstituted (C6-C30) aryl. R 4 and R 5 are each independently substituted with one or more substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl One or more substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic ring Wherein the fused 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted aromatic ring is one or more fused (C3-C30) cycloalkyl Organic light emitting compounds. 제 1항 또는 제 2항에 있어서,The method according to claim 1 or 2, 상기 R1 내지 R5 및 R11 내지 R18의 치환기는 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된 (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C6-C30)시클로알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, 아다만틸, (C7-C30)바이시클로알킬, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NR41R42, BR43R44, PR45R46, P(=O)R47R48[R41 내지 R48은 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이다.], (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성하는 것을 특징으로 하는 유기 발광 화합물.The substituents of R 1 to R 5 and R 11 to R 18 may be substituted or unsubstituted with (C1-C30) alkyl, (C6-C30) aryl, or (C6-C30) aryl substituted or unsubstituted with deuterium, halogen or halogen. Cyclic (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, at least one 5- to 7-membered heterocycloalkyl fused to at least one aromatic ring, (C3-C30) cycloalkyl, at least one aromatic ring Fused (C6-C30) cycloalkyl, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, adamantyl, (C7- C30) Bicycloalkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR 41 R 42 , BR 43 R 44 , PR 45 R 46 , P (= O) R 47 R 48 [R 41 to R 48 are independently of each other substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl. ], (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, (C1-C30) alkyloxy, (C1-C30) alkyl Thio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, (C6-C30) Aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nit The organic light emitting compound, characterized in that further substituted with one or more selected from the group consisting of or hydroxy, or adjacent substituents are connected to form a ring. 제 3항에 있어서,The method of claim 3, wherein 하기 화합물로부터 선택되는 것을 특징으로 하는 유기 발광 화합물.An organic light emitting compound, which is selected from the following compounds.
Figure 112009037622889-PAT00034
Figure 112009037622889-PAT00034
Figure 112009037622889-PAT00035
Figure 112009037622889-PAT00035
Figure 112009037622889-PAT00036
Figure 112009037622889-PAT00036
Figure 112009037622889-PAT00037
Figure 112009037622889-PAT00037
Figure 112009037622889-PAT00038
Figure 112009037622889-PAT00038
Figure 112009037622889-PAT00039
Figure 112009037622889-PAT00039
Figure 112009037622889-PAT00040
Figure 112009037622889-PAT00040
Figure 112009037622889-PAT00041
Figure 112009037622889-PAT00041
 제 1항 내지 제 4항에서 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 4. 제 5항에 있어서,The method of claim 5, 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 2 또는 화학식 3의 화합물에서 선택되는 도판트 하나 이상을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The organic electroluminescent device includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound and at least one dopant selected from a compound of Formula 2 or Formula 3 below. An organic electroluminescent device characterized by. [화학식 2][Formula 2]
Figure 112009037622889-PAT00042
Figure 112009037622889-PAT00042
 [화학식 3](3)
Figure 112009037622889-PAT00043
Figure 112009037622889-PAT00043
 [상기 화학식 3에서, Ar11 및 Ar12는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C4-C30)헤테로아릴, 치환 또는 비치환된 (C6-C30)아릴아미노, (C1-C30)알킬아미노, 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)시클로알킬이고, Ar11 및 Ar12는 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하고; [In Formula 3, Ar 11 and Ar 12 are independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C4-C30) hetero One or more fused aryl, substituted or unsubstituted (C6-C30) arylamino, (C1-C30) alkylamino, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted aromatic rings 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring is a (C3-C30) cycloalkyl fused with one or more, Ar 11 and Ar 12 are Linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; c가 1인 경우 Ar13은 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C4-C30)헤테로아릴 또는 하기 구조에서 선택되는 치환기이고;when c is 1 Ar 13 is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C4-C30) heteroaryl or a substituent selected from the following structures;
Figure 112009037622889-PAT00044
Figure 112009037622889-PAT00044
 c가 2인 경우 Ar13는 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된(C4-C30)헤테로아릴렌 또는 하기 구조에서 선택되는 치환기이고;when c is 2, Ar 13 is substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C4-C30) heteroarylene or a substituent selected from the following structures;
Figure 112009037622889-PAT00045
Figure 112009037622889-PAT00045
 Ar14 및 Ar15은 서로 독립적으로 치환 또는 비치환된(C6-C30)아릴렌 또는 치환 또는 비치환된(C4-C30)헤테로아릴렌이고;Ar 14 and Ar 15 are each independently substituted or unsubstituted (C6-C30) arylene or substituted or unsubstituted (C4-C30) heteroarylene; R101 내지 R103는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬 또는 치환 또는 비치환된(C6-C30)아릴이고;R 101 to R 103 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl; d는 1 내지 4의 정수이며, e는 0 또는 1의 정수이다.]d is an integer of 1 to 4, and e is an integer of 0 or 1.] 제 6항에 있어서,The method of claim 6, 상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자. An organic electroluminescent device comprising at least one compound selected from the group consisting of an arylamine compound or a styrylarylamine compound in the organic layer. 제 6항에 있어서,The method of claim 6, 상기 유기물층에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함하는 것을 특징으로 하는 유기 전계 발광 소자.An organic electric field further comprising at least one metal or a complex compound selected from the group consisting of Group 1, Group 2, 4, 5 cycle transition metals, lanthanum series metals and organic metals of d-transition elements in the organic layer. Light emitting element. 제 6항에 있어서,The method of claim 6, 상기 유기물층은 발광층 및 전하생성층을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer. 제 6항에 있어서,The method of claim 6, 상기 유기물층에 적색, 녹색 또는 청색 발광을 하는 유기화합물층 하나 이상을 더 포함하여 백색 발광을 하는 유기 전계 발광 소자.An organic electroluminescent device for emitting white light, further comprising at least one organic compound layer emitting red, green, or blue light in the organic material layer.
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