KR20110008723A - 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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KR20110008723A
KR20110008723A KR1020090066210A KR20090066210A KR20110008723A KR 20110008723 A KR20110008723 A KR 20110008723A KR 1020090066210 A KR1020090066210 A KR 1020090066210A KR 20090066210 A KR20090066210 A KR 20090066210A KR 20110008723 A KR20110008723 A KR 20110008723A
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substituted
unsubstituted
alkyl
aryl
light emitting
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김치식
음성진
조영준
권혁주
김봉옥
김성민
윤승수
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다우어드밴스드디스플레이머티리얼 유한회사
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Priority to KR1020090066210A priority Critical patent/KR20110008723A/en
Priority to PCT/KR2010/004693 priority patent/WO2011010840A1/en
Priority to TW099123759A priority patent/TW201111472A/en
Publication of KR20110008723A publication Critical patent/KR20110008723A/en

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Abstract

PURPOSE: An organic electroluminescent compound is provided to ensure excellent luminous efficiency and lifetime property of materials and to prepare an OLED device with excellent driving durability of a device. CONSTITUTION: An organic electroluminescent compound is represented by chemical formula 1. In chemical formula 1, R1 - R10 are independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, and one or more substituted or unsubstituted (C6-C30) aryl fused with substituted or unsubstituted (C3-C30) cycloalkyl; W is -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-; and m is 1 or 2.

Description

신규한 유기 발광 화합물 및 이를 포함하는 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 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 a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly to a novel organic light emitting compound used as a light emitting material and an organic electroluminescent device employing the same as a host.

인광 발광체의 호스트 재료로는 현재까지 CBP가 가장 널리 알려져 있으며, BCP 및 BAlq 등의 정공차단층을 적용한 고효율의 OLED, BAlq 유도체를 호스트로 이용한 고성능의 OLED가 공지되어 있다.CBP is most widely known as a host material for phosphorescent emitters, and a high-performance OLED using a high-efficiency OLED and a BAlq derivative applied to a hole blocking layer such as BCP and BAlq as a host is known.

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. OLED에서 전력효율 = (π/전압) × 전류효율 이므로, 전력효율은 전압에 반비례하는데, OLED의 소비 전력이 낮으려면 전력 효율이 높아야한다. 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. 또한, OLED 소자에서의 수명 측면에서도 결코 만족할만한 수준이 되질 못하여 더욱 안정되고, 더욱 성능이 뛰어난 호스트 재료의 개발이 요구되고 있다.However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is not very good, and thus has a disadvantage such that the material changes when undergoing a high temperature deposition process under vacuum. Since power efficiency = (π / voltage) × current efficiency in OLEDs, power efficiency is inversely proportional to voltage. However, low power consumption of OLEDs requires high power efficiency. Actually, OLEDs using phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials.However, when a conventional material such as BAlq or CBP is used as a host of phosphorescent materials, OLEDs using fluorescent materials Compared with the higher driving voltage, there was no significant advantage in terms of power efficiency (lm / w). 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 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.Accordingly, the present inventors have endeavored to solve the above-mentioned conventional problems. As a result, the present inventors have invented a new light emitting compound for realizing an organic electroluminescent device having excellent luminous efficiency and dramatically improved lifespan.

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

본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 기존 호스트 재료에 비해 발광효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 양호한 OLED를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by Formula 1 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has better luminous efficiency and excellent life characteristics of the material than the conventional host material to drive the device There is an advantage that an OLED having a very long life can be manufactured.

[화학식 1][Formula 1]

Figure 112009044256150-PAT00002
Figure 112009044256150-PAT00002

[상기 화학식 1에 있어서,[In Formula 1,

R1 내지 R10은 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, NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C2-C30)알키닐,

Figure 112009044256150-PAT00003
또는
Figure 112009044256150-PAT00004
이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로 방향족 고리를 형성할 수 있으며; W는 -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- 또는 -B(R58)-이고, R51 내지 R58 및 R61 내지 R63은 상기 R1 내지 R10에서의 정의와 동일하고; 상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하며; 상기 R21 내지 R28은 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이고, 상기 Ra, Rb, Rc, Rd는 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이며, 상기 Y는 S 또는 O이고, 상기 Re, Rf는 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C6-C30)아릴옥시이며; m은 1 또는 2의 정수이다.]R 1 to R 10 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, or 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 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= 0) R 27 R 28 , R a R b R c Si-, R d Y-, R e C (= 0)-, R f C (= 0) O-, substituted or unsubstituted ( C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,
Figure 112009044256150-PAT00003
or
Figure 112009044256150-PAT00004
Alicyclic ring and monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic ring, connected by (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings Can form; W is-(CR 51 R 52 ) m -,-(R 51 ) C = C (R 52 )-, -N (R 53 )-, -S-, -O-, -Si (R 54 ) (R 55 )-, -P (R 56 )-, -P (= 0) (R 57 )-, -C (= 0)-or -B (R 58 )-, and R 51 to R 58 and R 61 to R 63 is the same as defined above in R 1 to R 10 ; The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; R 21 to R 28 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, and R a , R b , R c , R d are each independently substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl, Y is S or O, and R e , R f is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C6-C30) Aryloxy; m is an integer of 1 or 2.]

본 발명에 기재된 “알킬”, “알콕시” 및 그 외 “알킬”부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함하고, 「시클로알킬」은 치환 또는 비치환된 아다만틸 또는 치환 또는 비치환된 (C7-C30)바이시클로알킬을 모두 포함한다. 본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 4 내지 7원, 바람직하게는 5 또는 6원을 포함하는 단일 또는 융합고리계를 포함하며, 하나이상의 아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. 상기 아릴의 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트라이페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 「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 6원의 단환 헤테로아릴 또는 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 화학결합을 통하여 결합되어 있는 구조도 포함된다. 상기 헤테로아릴기는 고리 내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 상기 헤테로아릴의 구체적인 예로 퓨릴, 티에닐, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아지닐, 테트라지닐, 트리아졸릴, 테트라졸릴, 퓨라자닐, 피리딜, 피라지닐, 피리미디닐, 피리다지닐 등의 단환 헤테로아릴, 벤조퓨릴, 벤조티에닐, 이소벤조퓨릴, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴놀리진일, 퀴녹살리닐, 카바졸릴, 페난트리디닐, 벤조디옥솔릴 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다.Substituents comprising the "alkyl", "alkoxy" and other "alkyl" moieties described herein include both straight or crushed forms, and "cycloalkyl" is substituted or unsubstituted adamantyl or substituted or unsubstituted And (C7-C30) bicycloalkyl. "Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and includes a single or fused ring system containing 4 to 7 members, preferably 5 or 6 members, and at least one aryl It also includes structures bonded through this chemical bond. Specific examples of the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. Including but not limited to. "Heteroaryl" means an aryl group containing 1 to 4 heteroatoms selected from N, O and S as an aromatic ring skeleton atom, and the remaining aromatic ring skeleton atoms are carbon, and a 5 to 6 membered monocyclic heteroaryl Or polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. In addition, heteroaryl in the present invention also includes a structure in which one or more heteroaryl is bonded through a chemical bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples of the heteroaryl include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, tria Monocyclic heteroaryl such as zolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, benzoimidazolyl, benzothiazolyl, benzoiso Thiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinolinyl, quinazolinyl, quinolizinyl, quinoxalinyl, carba Polycyclic heteroaryls such as zolyl, phenantridinyl, benzodioxolyl and the like, and their corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like. It is not limited to this.

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

또한 본 발명에 기재되어 있는 “치환 또는 비치환”에 있어서, 치환은 서로 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 (C3-C30)시클로알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (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 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성할 수 있고, 상기 R31 내지 R38은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴인 것을 의미한다.In addition, in the "substituted or unsubstituted" described in the present invention, the substitution is independently of each other deuterium, halogen, halogen substituted (C1-C30) alkyl, (C6-C30) aryl, (C6-C30 (C3-C30) heteroaryl substituted or unsubstituted, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30) cycloalkyl , (C3-C30) cycloalkyl fused with one or more aromatic rings, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, ( C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR 31 R 32 , BR 33 R 34 , PR 35 R 36 , P (= O) R 37 R 38 , (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) alkoxycar At least one selected from the group consisting of niyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nitro or hydroxy Or a substituent adjacent to each other may be linked to each other to form a ring, wherein R 31 to R 38 are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 3 -C 30) heteroaryl. it means.

상기 R1 내지 R10, R21 내지 R28, R51 내지 R58 및 R61 내지 R63은 서로 독립적으로 수소, 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, 1,2-디하이드로아세나프틸 등의 시클로알킬이 하나 이상 융합된 아릴, 디벤조티오페닐, 디벤조퓨릴, 카바졸릴, 피리딜, 퓨릴, 티에닐, 퀴놀릴, 트리아지닐, 피리미디닐, 피리다지닐, 퀴녹살리닐, 페난트롤리닐 등의 헤테로아릴, 벤조피롤리디노, 벤조피페리디노, 디벤조모폴리노, 디벤조아제피노 등의 하나 이상의 방향족고리가 융합된 헤테로시클로알킬, 페닐, 나프틸, 플루오레닐, 바이페닐, 페난트릴, 터페닐, 피레닐, 퍼릴레닐, 스피로바이플루오레닐, 플루오란테닐, 크리세닐, 트리페닐레닐 등의 아릴 또는 디벤조티오페닐, 디벤조퓨릴, 카바졸릴, 피리딜, 퓨릴, 티에닐, 퀴놀릴, 트리아지닐, 피리미디닐, 피리다지닐, 퀴녹살리닐, 페난트롤리닐 등의 헤테로아릴이 치환된 아미노, 비페닐옥시 등의 아릴옥시, 비페닐티오 등의 아릴티오, 비페닐메틸, 트리페닐메틸 등의 아르알킬, 카르복실, 나이트로,

Figure 112009044256150-PAT00005
,
Figure 112009044256150-PAT00006
또는 하이드록시로부터 선택되어지나, 이에 한정되는 것은 아니며, 상기 화학식 1에서와 같이 더 치환될 수 있다.R 1 to R 10 , R 21 to R 28 , R 51 to R 58 and R 61 to R 63 are each independently hydrogen, halogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, alkyl, phenyl, naph Aryl, 1,2-dihydroacenaphyl, such as butyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perrylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl Aryl, dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl Heterocycloalkyl, phenyl, naphthyl, fluorenyl, fused with one or more aromatic rings such as heteroaryl such as phenanthrolinyl, benzopyrrolidino, benzopiperidino, dibenzomorpholino, dibenzoazino, Biphenyl, phenanthryl, terphenyl, pyrenyl, perilenyl, spirobifluorenyl, Aryl or dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxali, such as laurantenyl, chrysenyl, triphenylenyl, etc. Aryloxy, such as amino, biphenyloxy, and arylthio such as amino, biphenyloxy, and the like, which are substituted by heteroaryl such as aryl and phenanthrolinyl, aralkyl such as biphenylmethyl, triphenylmethyl, carboxyl, nitro,
Figure 112009044256150-PAT00005
,
Figure 112009044256150-PAT00006
Or hydroxy, but is not limited thereto, and may be further substituted as in Chemical Formula 1.

상기 R1 내지 R10은 하기 구조로 예시되어지나, 이에 한정되는 것은 아니다.The R 1 to R 10 is illustrated by the following structure, but is not limited thereto.

Figure 112009044256150-PAT00007
Figure 112009044256150-PAT00007

Figure 112009044256150-PAT00008
Figure 112009044256150-PAT00008

[R71 내지 R172는 서로 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)시클로알킬이 하나이상 융합된 (C6-C30)아릴, (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 아미노, (C1-C30)알킬아미노, (C6-C30)아릴아미노, NR41R42, BR43R44, PR45R46, P(=O)R47R48, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C2-C30)알케닐, (C2-C30)알키닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고, 상기 R41 내지 R48은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이다.][R 71 to R 172 independently of one another are hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl, wherein one or more fused (C6-C30) cycloalkyl is ( C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, cyano, amino, (C1-C30) alkylamino, (C6-C30) arylamino, NR 41 R 42 , BR 43 R 44 , PR 45 R 46 , P (= O) R 47 R 48 , tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) aryl Silyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1- C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nitro or hydroxy Can be linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents to form an alicyclic ring and a monocyclic or polycyclic aromatic ring , R 41 to R 48 are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl.]

본 발명의 R1 내지 R10은 하기 구조로 예시되어지나, 이에 한정되는 것은 아니다.R 1 to R 10 of the present invention is illustrated by the following structure, but is not limited thereto.

Figure 112009044256150-PAT00009
Figure 112009044256150-PAT00009

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 112009044256150-PAT00010
Figure 112009044256150-PAT00010

Figure 112009044256150-PAT00011
Figure 112009044256150-PAT00011

Figure 112009044256150-PAT00012
Figure 112009044256150-PAT00012

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 112009044256150-PAT00013
Figure 112009044256150-PAT00013

[상기 반응식 1에서 R1 내지 R10은 상기 화학식 1에서의 정의와 동일하다.][In Formula 1, R 1 to R 10 are the same as defined in Formula 1 above.]

또한 본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. 상기 유기 발광 화합물은 발광층의 호스트 물질로 사용되어진다.In another aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound of Formula 1. The organic light emitting compound is used as a host material of the light emitting layer.

본 발명에 따른 유기 전계 발광 소자는 상기 유기물층이 발광층을 포함하며, 상기 발광층은 상기 화학식 1의 유기 발광 화합물 하나 이상과 하기 화학식 2로 표시되는 도판트 하나 이상을 더 포함하는 것을 특징으로 하며, 본 발명의 유기 전계 발광 소자에 적용되는 발광 도판트는 특별히 제한되지는 않으나, 하기 화학식 2의 화합물로 예시될 수 있다.The organic electroluminescent device according to the present invention is characterized in that the organic material layer includes a light emitting layer, and the light emitting layer further includes at least one organic light emitting compound of Formula 1 and at least one dopant represented by the following Formula 2. The light emitting dopant applied to the organic electroluminescent device of the invention is not particularly limited, but may be exemplified by the compound represented by the following Chemical Formula 2.

[화학식 2][Formula 2]

MM 1One LL 101101 LL 102102 LL 103103

[상기 화학식 2에서,[In Formula 2,

M1은 7족, 8족, 9족, 10족, 11족, 13족, 14족, 15족 및 16족의 금속으로 이루어진 군으로부터 선택되고, 리간드 L101, L102 및 L103은 서로 독립적으로 하기 구조로부터 선택되며;M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L 101 , L 102 and L 103 are independent of each other It is selected from the following structures;

Figure 112009044256150-PAT00014
Figure 112009044256150-PAT00014

Figure 112009044256150-PAT00015
Figure 112009044256150-PAT00015

상기 R201 내지 R203은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;R 201 to R 203 are each independently hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a (C1-C30) aryl substituted or unsubstituted (C6-C30) aryl or halogen;

R204 내지 R219는 서로 독립적으로 수소, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고, R 204 to R 219 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted Or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen,

R220 내지 R223은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;R 220 to R 223 are independently of each other hydrogen, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl;

R224 및 R225는 서로 독립적으로 수소, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R 224 and R 225 are independently of each other hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain or contain fused rings Unsubstituted (C3-C12) alkylene or (C3-C12) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

R226은 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C5-C30)헤테로아릴 또는 할로겐이고;R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen;

R227 내지 R229는 서로 독립적으로 수소, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 할로겐이고;R 227 to R 229 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;

Q는

Figure 112009044256150-PAT00016
,
Figure 112009044256150-PAT00017
또는
Figure 112009044256150-PAT00018
이며, R231 내지 R242는 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된 (C6-C30)아릴, 시아노, 치환 또는 비치환된 (C5-C30)시클로알킬이거나, 인접한 치환체와 알킬렌 또는 알케닐렌으로 연결되어 스피로 고리 또는 융합고리를 형성할 수 있거나, R207 또는 R208과 알킬렌 또는 알케닐렌으로 연결되어 포화 또는 불포화의 융합고리를 형성할 수 있다.]Q is
Figure 112009044256150-PAT00016
,
Figure 112009044256150-PAT00017
or
Figure 112009044256150-PAT00018
R 231 to R 242 are each independently hydrogen, a substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, cyano , Substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to an adjacent substituent by alkylene or alkenylene to form a spiro ring or fused ring, or by R 207 or R 208 to alkylene or alkenylene To form saturated or unsaturated fused rings.]

상기 화학식 2의 M1은 Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au 및 Ag로부터 선택되며, 상기 화학식 2의 화합물은 한국특허출원번호 제10-2009-0037519호에 예시된 것도 포함하나, 이에 한정되지는 않는다.M 1 of Chemical Formula 2 is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag, wherein the compound of Chemical Formula 2 is Korean Patent Application No. It includes, but is not limited to, those illustrated in No. 10-2009-0037519.

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

또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 발광 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 상기 유기물층은 발광층과 전하생성층을 동시에 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 metal or complex compound selected from, the organic material layer may include a light emitting layer and a charge generating layer at the same time.

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.In addition, an organic electroluminescent device that emits white light may be formed in the organic material layer by simultaneously including one or more organic light emitting layers emitting blue, red, or green light in addition to the organic light emitting compound.

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

이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명하나, 이는 단지 그 실시 양태를 예시하기 위한 것일 뿐, 본 발명의 범위를 한정하는 것은 아니다.Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same and a light emitting property of the device are described for the detailed understanding of the present invention, but the present invention is only intended to illustrate the embodiments of the present invention. It does not limit the scope of the invention.

[제조예][Manufacturing Example]

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

Figure 112009044256150-PAT00019
Figure 112009044256150-PAT00019

화합물 compound 1-11-1 의 제조Manufacture

4H-1,2,4-triazole 10 g(144.78 mmol)과 MC 50 mL를 혼합한 후, Br2 48.5 g와 MC 50 mL의 혼합물을 천천히 첨가하였다. 이 후 2M NaOH 수용액 217 mL을 천천히 첨가한 후 상온에서 2시간 동안 교반하였다. 증류수를 넣고 MC로 추출한 다음 황산마그네슘으로 건조하고 감압 증류한 후, 컬럼 분리하여 화합물 1-1 17 g(74.93 mmol, 52.03 %) 을 얻었다.After mixing 10 g (144.78 mmol) of 4H-1,2,4-triazole and 50 mL of MC, a mixture of 48.5 g of Br 2 and 50 mL of MC was slowly added. Then 217 mL of 2M NaOH aqueous solution was slowly added, followed by stirring at room temperature for 2 hours. Distilled water was added thereto, followed by extraction with MC, followed by drying with magnesium sulfate, distillation under reduced pressure, and column separation to obtain compound 1-1 17 g (74.93 mmol, 52.03%).

화합물 compound 1-21-2 의 제조Manufacture

화합물 1-1 17 g(74.93 mmol), iodobenzene 12.5 mL(112.4 mmol), Cu 7.14 g(112.4 mmol), K2CO3 31.07 g(224.8 mmol), 18-Crown-6 1.58 g(5.99 mmol), 1,2-dichlorobenzene 100 mL를 혼합하여 180 ℃에서 12시간 동안 교반하였다. 상온으로 냉각하고 유기 용매를 감압 증류한 후, 증류수를 넣고 EA로 추출하였다. 황산마그네슘으로 건조하고 감압 증류한 후, 컬럼 분리하여 화합물 1-2 14 g(46.21 mmol, 62.16 %)을 얻었다. 17 g (74.93 mmol) of compound 1-1 , 12.5 mL (112.4 mmol) of iodobenzene, 7.14 g (112.4 mmol) of Cu, 31.07 g (224.8 mmol) of K 2 CO 3 , 1.58 g (5.99 mmol) of 18-Crown-6, 100 mL of 1,2-dichlorobenzene was mixed and stirred at 180 ° C. for 12 hours. After cooling to room temperature, the organic solvent was distilled under reduced pressure, distilled water was added and extracted with EA. Drying over magnesium sulfate, distillation under reduced pressure, and column separation yielded Compound 1-2 (14 g, 46.21 mmol, 62.16%).

화합물 compound 1-31-3 의 제조Manufacture

화합물 1-2 14 g(46.21 mmol), phenylboronic acid 8.45 g(69.31 mmol), Pd(PPh3)4 1.6 g(1.38 mmol), Na2CO3 14.69 g(138.6 mmol), 증류수 70 mL, 톨루엔 100 mL을 혼합하여 환류 교반하였다. 12시간 후 상온으로 냉각하고 EA로 추출하고 증류수로 씻어 주었다. 황산마그네슘으로 건조하고 감압 증류한 후, 컬럼 분리하여 화합물 1-3 12 g(39.98 mmol, 84.78 %)을 얻었다. Compound 1-2 14 g (46.21 mmol), phenylboronic acid 8.45 g (69.31 mmol), Pd (PPh 3 ) 4 1.6 g (1.38 mmol), Na 2 CO 3 14.69 g (138.6 mmol), distilled water 70 mL, toluene 100 The mL was mixed and stirred at reflux. After 12 hours, the mixture was cooled to room temperature, extracted with EA, and washed with distilled water. After drying over magnesium sulfate, distillation under reduced pressure, and column separation yielded Compound 1-3 12 g (39.98 mmol, 84.78%).

화합물 compound 1One 의 제조Manufacture

화합물 1-3 12 g(39.98 mmol), carbazole 8.69 g(51.97 mmol), Cu 3.81 g(59.97 mmol), K2CO3 16.57 g(119.97 mmol), 18-crown-6 0.84 g(3.19 mmol), 1,2-dichlorobenzene 100 mL을 혼합하여 180 ℃에서 24시간 동안 교반하였다. 상온으로 냉각하고 유기 용매를 감압 증류한 후, 증류수를 넣고 EA로 추출하였다. 황산마그네슘으로 건조하고 감압 증류한 후, 컬럼 분리하여 화합물 1 9 g(23.28 mmol, 58.24 %)을 얻었다. Compound 1-3 12 g (39.98 mmol), carbazole 8.69 g (51.97 mmol), Cu 3.81 g (59.97 mmol), K 2 CO 3 16.57 g (119.97 mmol), 18-crown-6 0.84 g (3.19 mmol), 100 mL of 1,2-dichlorobenzene was mixed and stirred at 180 ° C. for 24 hours. After cooling to room temperature, the organic solvent was distilled under reduced pressure, distilled water was added and extracted with EA. Drying over magnesium sulfate, distillation under reduced pressure, and column separation yielded Compound 1 9 g (23.28 mmol, 58.24%).

[제조예 2]화합물 43의 제조Preparation Example 2 Preparation of Compound 43

Figure 112009044256150-PAT00020
Figure 112009044256150-PAT00020

화합물 compound 2-12-1 의 제조Manufacture

화합물 1-2 17 g(74.93 mmol), 1-iodonaphthalene 28.5 g(112.4 mmol), Cu 7.14 g(112.4 mmol), K2CO3 31.07 g(224.8 mmol), 18-Crown-6 1.58 g(5.99 mmol), 1,2-dichlorobenzene 100 mL을 혼합하여 180 ℃에서 12시간 동안 교반하였다. 상온으로 냉각하고 유기 용매를 감압 증류한 후, 증류수를 넣고 EA로 추출하였다. 황산마그네슘으로 건조하고 감압 증류한 후, 컬럼 분리하여 화합물 2-1 13 g(36.82 mmol, 49.14 %)을 얻었다. Compound 1-2 17 g (74.93 mmol), 28.5 g (112.4 mmol) 1-iodonaphthalene, 7.14 g (112.4 mmol) Cu, 31.07 g (224.8 mmol) K 2 CO 3 , 1.58 g (5.99 mmol) 18-Crown-6 ), And 100 mL of 1,2-dichlorobenzene were mixed and stirred at 180 ° C. for 12 hours. After cooling to room temperature, the organic solvent was distilled under reduced pressure, distilled water was added and extracted with EA. Drying over magnesium sulfate, distillation under reduced pressure, and column separation yielded Compound 2-1 13 g (36.82 mmol, 49.14%).

화합물 compound 2-22-2 의 제조Manufacture

화합물 2-1 13 g(36.82 mmol)을 제조예 1에서 화합물 1-3의 제조와 동일한 방법으로 합성하여 화합물 2-2 8 g(22.84 mmol, 62.04 %)을 얻었다. 13 g (36.82 mmol) of compound 2-1 were synthesized in the same manner as in the preparation of compound 1-3 in Preparation Example 1, to obtain 8 g (22.84 mmol, 62.04%) of compound 2-2 .

화합물 compound 4343 의 제조Manufacture

화합물 2-2 8 g(22.84 mmol)을 제조예 1에서 화합물 1의 제조와 동일한 방법으로 합성하여 화합물 43 6 g(13.74 mmol, 60.18 %)을 얻었다. Compound 2-2 8 g (22.84 mmol) synthesized in the same manner as in the preparation of compound 1 in Production Example 1 to obtain the title compound 43 6 g (13.74 mmol, 60.18 %).

상기 제조예 1 및 2의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 85를 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to 85 were prepared using the methods of Preparation Examples 1 and 2, and 1 H NMR and MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.

[표 1]TABLE 1

Figure 112009044256150-PAT00021
Figure 112009044256150-PAT00021

Figure 112009044256150-PAT00022
Figure 112009044256150-PAT00022

Figure 112009044256150-PAT00023
Figure 112009044256150-PAT00023

Figure 112009044256150-PAT00024
Figure 112009044256150-PAT00024

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

본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다.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 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.Next, an ITO substrate is installed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2) having the structure -TNATA), evacuated until the vacuum in the chamber reached 10 -6 torr, and then applied a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate.

이어서, 진공 증착 장비 내의 다른 셀에 하기구조 N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.The NPB -diphenyl-4,4'-diamine into the (NPB), by applying a current to the cell - Then, to another cell of the vacuum vapor-deposit device structure, N, N 'N, N -bis (α-naphthyl)' A 20 nm thick hole transport layer was deposited on the hole injection layer by evaporation.

정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착 시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명에 따른 화합물 7을 넣고, 또 다른 셀에는 도판트로서 하기 구조의 화합물 Iridium(III) tris(2-phenylpyridine) (Ir(ppy)3)를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 4 내지 15%중량으로 도핑함으로써 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. In one cell of the vacuum deposition equipment, Compound 7 according to the present invention was put as a host, and in another cell, the compound Iridium (III) tris (2-phenylpyridine) (Ir (ppy) 3 ) having the following structure was added as a dopant, respectively. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by evaporating the two materials at different rates and doping at 4 to 15% by weight.

이어서 상기 발광층 위에 정공차단층으로 Bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum(III) (BAlq)을 5 nm의 두께로 증착시키고, 전자전달층으로써 하기 구조의 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 하기 구조의 화합물 lithium quinolate (Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다. Subsequently, Bis (2-methyl-8-quinolinato) ( p- phenylphenolato) aluminum (III) (BAlq) was deposited to a thickness of 5 nm on the light emitting layer with a hole blocking layer, and tris (8-) having the following structure as an electron transport layer. hydroxyquinoline) -aluminum (III) (Alq) was deposited to a thickness of 20 nm, and then the compound lithium quinolate (Liq) having the following structure was deposited to a thickness of 1 to 2 nm using an electron injection layer, and then another vacuum deposition equipment was used. An Al cathode was deposited to a thickness of 150 nm to produce an OLED.

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.

[실시예 2]본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 2 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

정공차단층을 사용하지 않는 것을 제외하고는 실시예 1과 동일한 방법으로 OLED를 제작하였다. An OLED was manufactured in the same manner as in Example 1, except that the hole blocking layer was not used.

[실시예 3] 본 발명에 따른 유기발광화합물을 이용한 OLED 소자 제작Example 3 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광층에서 호스트를 본 발명의 화합물 12, 도판트를 bis(1- phenylisoquinolinato-N,C2’)iridium(acetylacetonate) ((piq)2Ir(acac))을 사용한 것을 제외하고는 실시예 2와 동일한 방법으로 OLED소자를 제작하였다.Compound 12 of the present invention in the light emitting layer, An OLED device was manufactured in the same manner as in Example 2, except that bis (1-phenylisoquinolinato-N, C 2 ′ ) iridium (acetylacetonate) ((piq) 2 Ir (acac)) was used as the dopant.

[비교예 1] 종래의 발광 재료를 이용한 OLED 소자의 발광 특성[Comparative Example 1] Light emission characteristics of OLED device using conventional light emitting material

진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 4,4'-bis(carbazol-9-yl)biphenyl (CBP)를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that 4,4'-bis (carbazol-9-yl) biphenyl (CBP) was used instead of the compound of the present invention as a host material in one cell in a vacuum deposition apparatus. .

[비교예 2] 종래의 발광 재료를 이용한 OLED 소자의 발광 특성Comparative Example 2 Light Emitting Characteristics of OLED Devices Using Conventional Light-Emitting Materials

진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 4,4'-bis(carbazol-9-yl)biphenyl (CBP)를 사용하고, 정공차단층으로 Bis(2-methyl-8-quinolinato)(p-phenyl-phenolato)aluminum(III) (BAlq)을 사용한 것을 제외하고는 실시예 3과 동일한 방법으로 OLED소자를 제작하였다.4,4'-bis (carbazol-9-yl) biphenyl (CBP) is used as a host material in one cell in the vacuum deposition apparatus, and Bis (2-methyl-8-quinolinato) is used as the hole blocking layer. An OLED device was manufactured in the same manner as in Example 3, except that ( p- phenyl-phenolato) aluminum (III) (BAlq) was used.

상기 실시예 1내지 3과 비교예 1 내지 2에서 제조된 본 발명에 따른 유기 발광 화합물과 종래의 발광 화합물을 함유하는 OLED 소자의 발광 효율을 각각 1,000 cd/m2 에서 측정하여 하기 표 2에 나타내었다. The luminous efficiency of the organic light emitting compound according to the present invention prepared in Examples 1 to 3 and Comparative Examples 1 and 2 and a conventional light emitting compound are measured at 1,000 cd / m 2 and are shown in Table 2 below. It was.

[표 2]TABLE 2

Figure 112009044256150-PAT00025
Figure 112009044256150-PAT00025

상기 표 2로부터 본 발명에서 개발한 유기 발광 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 발광 화합물을 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 0.4~3.7 lm/W의 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있다.It can be seen from Table 2 that the luminescent properties of the organic light emitting compounds developed in the present invention show superior properties compared to conventional materials. In addition, the device using the organic light emitting compound according to the present invention as a host material is not only excellent in the light emission characteristics, but also by lowering the driving voltage can lead to an increase in power efficiency of 0.4 ~ 3.7 lm / W to improve the power consumption.

Claims (10)

하기 화학식 1로 표시되는 유기 발광 화합물.An organic light emitting compound represented by Formula 1 below. [화학식 1][Formula 1]
Figure 112009044256150-PAT00026
Figure 112009044256150-PAT00026
 [상기 화학식 1에 있어서,[In Formula 1, R1 내지 R10은 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, NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C2-C30)알키닐,
Figure 112009044256150-PAT00027
또는
Figure 112009044256150-PAT00028
이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로 방향족 고리를 형성할 수 있으며; W는 -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- 또는 -B(R58)-이고, R51 내지 R58 및 R61 내지 R63은 상기 R1 내지 R10에서의 정의와 동일하고; 상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하며; 상기 R21 내지 R28은 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C3-C30)헤테로아릴이고, 상기 Ra, Rb, Rc, Rd는 서로 독립적으로 치환 또는 비치환된 (C1-C30)알킬 또는 치환 또는 비치환된 (C6-C30)아릴이며, 상기 Y는 S 또는 O이고, 상기 Re, Rf는 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된 (C6-C30)아릴옥시이며; m은 1 또는 2의 정수이다.]R 1 to R 10 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, or 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 21 R 22 , BR 23 R 24 , PR 25 R 26 , P (= 0) R 27 R 28 , R a R b R c Si-, R d Y-, R e C (= 0)-, R f C (= 0) O-, substituted or unsubstituted ( C6-C30) ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl,
Figure 112009044256150-PAT00027
or
Figure 112009044256150-PAT00028
Alicyclic ring and monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic ring, connected by (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings Can form; W is-(CR 51 R 52 ) m -,-(R 51 ) C = C (R 52 )-, -N (R 53 )-, -S-, -O-, -Si (R 54 ) (R 55 )-, -P (R 56 )-, -P (= 0) (R 57 )-, -C (= 0)-or -B (R 58 )-, and R 51 to R 58 and R 61 to R 63 is the same as defined above in R 1 to R 10 ; The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; R 21 to R 28 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl, and R a , R b , R c , R d are each independently substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl, Y is S or O, and R e , R f is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C6-C30) Aryloxy; m is an integer of 1 or 2.] 제 1항에 있어서,The method of claim 1, 상기 R1 내지 R10, R21 내지 R28, R51 내지 R58 및 R61 내지 R63의 “치환 또는 비치환”에 있어서, 치환은 서로 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 (C3-C30)시클로알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (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 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성할 수 있고, 상기 R31 내지 R38은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴인 것을 특징으로 하는 유기 발광 화합물.R 1 to R 10 , In the “substituted or unsubstituted” of R 21 to R 28 , R 51 to R 58, and R 61 to R 63 , the substitutions are independently of each other deuterium, halogen, (C1-C30) alkyl substituted or unsubstituted, (C6-C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered fused at least one aromatic ring Heterocycloalkyl, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl , Tri (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, NR 31 R 32 , BR 33 R 34 , PR 35 R 36 , P (= O) R 37 R 38 , (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) aryloxycarbon Neal, ( Consisting of C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nitro or hydroxy One or more substituents selected from the group or substituents adjacent to each other may be linked to each other to form a ring, wherein R 31 to R 38 may be independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3- C30) an organic light emitting compound, characterized in that heteroaryl. 제 1항에 있어서,The method of claim 1, 상기 R1 내지 R10은 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.The R 1 to R 10 is an organic light emitting compound, characterized in that selected from the following structure.
Figure 112009044256150-PAT00029
Figure 112009044256150-PAT00029
 [R71 내지 R172는 서로 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)시클로알킬이 하나이상 융합된 (C6-C30)아릴, (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 아미노, (C1-C30)알킬아미노, (C6-C30)아릴아미노, NR41R42, BR43R44, PR45R46, P(=O)R47R48, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6- C30)아릴실릴, 트리(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C2-C30)알케닐, (C2-C30)알키닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시이거나 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고, 상기 R41 내지 R48은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이다.][R 71 to R 172 independently of one another are hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl, wherein one or more fused (C6-C30) cycloalkyl is ( C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused with one or more aromatic rings, cyano, amino, (C1-C30) alkylamino, (C6-C30) arylamino, NR 41 R 42 , BR 43 R 44 , PR 45 R 46 , P (= O) R 47 R 48 , tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) aryl Silyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyloxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1- C30) alkoxycarbonyl, (C1-C30) alkylcarbonyl, (C6-C30) arylcarbonyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxyl, nitro or hydroxy It may be linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings to form an alicyclic ring and a monocyclic or polycyclic aromatic ring. , Wherein R 41 to R 48 are independently of each other (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl group.] 제 3항에 있어서,The method of claim 3, wherein 상기 R1 내지 R10은 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.The R 1 to R 10 is an organic light emitting compound, characterized in that selected from the following structure.
Figure 112009044256150-PAT00030
Figure 112009044256150-PAT00030
Figure 112009044256150-PAT00031
Figure 112009044256150-PAT00031
 제 1항에 있어서, The method of claim 1, 하기 화합물로부터 선택되는 유기 발광 화합물.An organic light emitting compound selected from the following compounds.
Figure 112009044256150-PAT00032
Figure 112009044256150-PAT00032
Figure 112009044256150-PAT00033
Figure 112009044256150-PAT00033
Figure 112009044256150-PAT00034
Figure 112009044256150-PAT00034
 제 1항 내지 제 5항의 유기 발광 화합물을 포함하는 것을 특징으로 하는 유 기 전계 발광 소자.An organic electroluminescent device comprising the organic light emitting compound of claim 1. 제 6항에 있어서,The method of claim 6, 상기 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어져 있으며, 상기 유기물층은 상기 유기 발광 화합물 하나 이상과 하기 화학식 2로 표시되는 도판트 하나 이상을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The organic electroluminescent device includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode, wherein the organic material layer includes one or more organic light emitting compounds and one or more dopants represented by the following Chemical Formula 2. Light emitting element. [화학식 2][Formula 2] MM 1One LL 101101 LL 102102 LL 103103 [상기 화학식 2에서,[In Formula 2, M1은 7족, 8족, 9족, 10족, 11족, 13족, 14족, 15족 및 16족의 금속으로 이루어진 군으로부터 선택되고, 리간드 L101, L102 및 L103은 서로 독립적으로 하기 구조로부터 선택되며;M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16, and the ligands L 101 , L 102 and L 103 are independent of each other It is selected from the following structures;
Figure 112009044256150-PAT00035
Figure 112009044256150-PAT00035
Figure 112009044256150-PAT00036
Figure 112009044256150-PAT00036
 상기 R201 내지 R203은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고;R 201 to R 203 are each independently hydrogen, a substituted or unsubstituted (C1-C30) alkyl, a (C1-C30) aryl substituted or unsubstituted (C6-C30) aryl or halogen; R204 내지 R219는 서로 독립적으로 수소, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고, R 204 to R 219 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted Or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen, R220 내지 R223은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고;R 220 to R 223 are independently of each other hydrogen, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl; R224 및 R225는 서로 독립적으로 수소, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R 224 and R 225 are independently of each other hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain or contain fused rings Unsubstituted (C3-C12) alkylene or (C3-C12) alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; R226은 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C5-C30)헤테로아릴 또는 할로겐이고;R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen; R227 내지 R229는 서로 독립적으로 수소, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 할로겐이고;R 227 to R 229 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen; Q는
Figure 112009044256150-PAT00037
,
Figure 112009044256150-PAT00038
또는
Figure 112009044256150-PAT00039
이며, R231 내지 R242는 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된 (C6-C30)아릴, 시아노, 치환 또는 비치환된 (C5-C30)시클로알킬이거나, 인접한 치환체와 알킬렌 또는 알케닐렌으로 연결되어 스피로 고리 또는 융합고리를 형성할 수 있거나, R207 또는 R208과 알킬렌 또는 알케닐렌으로 연결되어 포화 또는 불포화의 융합고리를 형성할 수 있다.]Q is
Figure 112009044256150-PAT00037
,
Figure 112009044256150-PAT00038
or
Figure 112009044256150-PAT00039
R 231 to R 242 are each independently hydrogen, a substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, cyano , Substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to an adjacent substituent by alkylene or alkenylene to form a spiro ring or fused ring, or by R 207 or R 208 to alkylene or alkenylene To form saturated or unsaturated fused rings.] 제 7항에 있어서,The method of claim 7, wherein 상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어 진 군으로부터 선택된 하나 이상의 아민계 화합물 또는 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.At least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound in the organic layer or organic of group 1, group 2, 4, 5 cycle transition metal, lanthanide series metal and d-transition element An organic electroluminescent device further comprising at least one metal or complex compound selected from the group consisting of metals. 제 7항에 있어서,The method of claim 7, wherein 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 7항에 있어서,The method of claim 7, wherein 상기 유기물층에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자.An organic electroluminescent device which emits white light by simultaneously including at least one organic light emitting layer emitting blue, red or green light in the organic material layer.
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