KR20110049217A - 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 PDFInfo
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Abstract
Description
본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자에 관한 것으로, 보다 구체적으로는 발광 재료로서 사용되는 신규한 유기 발광 화합물 및 이를 호스트로서 채용하고 있는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly to a novel organic light emitting compound used as a light emitting material and an organic electroluminescent device employing the same as a host.
OLED에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재까지 형광 재료가 널리 사용되고 있으나, 전기발광의 메커니즘 상 인광 재료의 개발은 이론적으로 4배까지 발광 효율을 개선시킬 수 있는 가장 좋은 방법 중 하나이다. The most important factor determining the luminous efficiency in OLEDs is the luminous material. Fluorescent materials are widely used as the light emitting materials to date, but the development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to 4 times.
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 거 칠 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.
본 발명의 목적은 상기한 문제점들을 해결하기 위하여 기존의 호스트 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며, 또 다른 목적으로서 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다.Disclosure of Invention An object of the present invention is to provide an organic light emitting compound having an excellent luminescence efficiency and device lifetime, and having an appropriate color coordinate, in order to solve the above problems, and to emit the organic light emitting compound as another object. It is to provide an organic electroluminescent device having high efficiency and long life, which is employed as a material.
본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 기존 호스트 재료에 비해 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수할 뿐만 아니라 전력효율의 상승을 유도하여 소비전력이 개선된 OLED 소자를 제조할 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by the following Chemical Formula 1 and an organic electroluminescent device comprising the same, the organic light emitting compound according to the present invention has better luminous efficiency and excellent life characteristics of the material than the conventional host material to drive the device In addition to having a very long lifespan, there is an advantage of manufacturing an OLED device having improved power consumption by inducing an increase in power efficiency.
[화학식 1][Formula 1]
[상기 화학식 1에서,[In Formula 1,
A1 내지 A4는 서로 독립적으로 -C(R3)- 또는 -N-이며;A 1 to A 4 are each independently of the other -C (R 3 )-or -N-;
R1 내지 R3은 서로 독립적으로 -L1-L2-L3-R4이고; 상기 L1 내지 L3은 서로 독립 적으로 화학결합이거나, 치환 또는 비치환된(C6-C30)아릴렌, 치환 또는 비치환된(C3-C30)헤테로아릴렌, 치환 또는 비치환된(C3-C30)시클로알킬렌, 치환 또는 비치환된(C2-C30)알케닐렌 또는 치환 또는 비치환된(C2-C30)알키닐렌이며; 상기 R4는 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)시클로알킬이 하나 이상 융합된 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C3-C30)헤테로아릴, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, 시아노, 나이트로, NR11R12, BR13R14, PR15R16, P(=O)R17R18, R19R20R21Si-, R22Y-, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐, 또는 이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로방향족고리를 형성할 수 있으며; 상기 A고리 및 B고리는 서로 독립적으로 치환 또는 비치환된(C5-C30)사이클로알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C6-C30)헤테로아릴이고, 단, R1 내지 R3은 적어도 한 개 이상 또는 를 포함하며; 상기 R11 내지 R22는 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이고; 상기 Y는 S 또는 O이며; W는 -(CR41R42)m-, -(R41)C=C(R42)-, -N(R43)-, -S-, -O-, -Si(R44)(R45)-, -P(R46)-, -P(=O)(R47)-, -C(=O)- 또는 -B(R48)-이고, R31 내지 R33 및 R41 내지 R48은 상기 R1 내지 R3에서의 정의와 동일하며;R 1 to R 3 are, independently from each other, -L 1 -L 2 -L 3 -R 4 ; L 1 to L 3 are each independently a chemical bond, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (C3-C30) heteroarylene, substituted or unsubstituted (C3- C30) cycloalkylene, substituted or unsubstituted (C2-C30) alkenylene or substituted or unsubstituted (C2-C30) alkynylene; R 4 is hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) cycloalkyl fused at least one 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 At least one fused 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted aromatic ring and at least one fused (C3-C30) cycloalkyl, cyano, nitrate NR 11 R 12 , BR 13 R 14 , PR 15 R 16 , P (= O) R 17 R 18 , R 19 R 20 R 21 Si-, R 22 Y-, substituted or unsubstituted (C6-C30 ) Ar (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, or Or an alicyclic ring and a monocyclic or polycyclic aromatic ring, monocyclic or polycyclic heteroaromatic linked with (C3-C30) alkylene or (C3-C30) alkenylene with or without adjacent substituents and fused rings May form a ring; Ring A and Ring B are each independently substituted or unsubstituted (C5-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C6-C30) heteroaryl, provided that , R 1 to R 3 is at least one or It includes; R 11 to R 22 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30) heteroaryl; Y is S or O; W is-(CR 41 R 42 ) m -,-(R 41 ) C = C (R 42 )-, -N (R 43 )-, -S-, -O-, -Si (R 44 ) (R 45 )-, -P (R 46 )-, -P (= 0) (R 47 )-, -C (= 0)-, or -B (R 48 )-, R 31 to R 33 and R 41 to R 48 is as defined in R 1 to R 3 above;
상기 헤테로시클로알킬, 헤테로아릴 및 헤테로방향족고리는 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고; m은 0 내지 2의 정수이다.]The heterocycloalkyl, heteroaryl and heteroaromatic ring comprises one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P; m is an integer of 0 to 2.]
상기 A1 내지 A4는 서로 독립적으로 -C(R3)- 또는 -N-이고, 상기 A1 내지 A4는 서로 동일하거나 상이할 수 있으며, R1 내지 R3은 서로 독립적으로 -L1-L2-L3-R4이고, 상기 R1 내지 R3도 서로 동일하거나 상이할 수 있다.A 1 to A 4 are independently from each other -C (R 3 )-or -N-, A 1 to A 4 may be the same or different from each other, R 1 to R 3 are independently from each other -L 1 -L 2 -L 3 -R 4 , and the R One To R 3 It may be the same or different from each other.
본 발명에 기재된 ‘알킬’, ‘알콕시’ 및 그 외 ‘알킬’부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함하고, ‘시클로알킬’은 단일 고리계 뿐만 아니라 치환 또는 비치환된 아다만틸 또는 치환 또는 비치환된(C7-C30)바이시클 로알킬과 같은 여러 고리계 탄화수소도 포함한다.Substituents comprising the 'alkyl', 'alkoxy' and other 'alkyl' moieties described herein include both straight or crushed forms, and 'cycloalkyl' is substituted or unsubstituted as well as a single ring system Or several ring-based hydrocarbons such as substituted or unsubstituted (C7-C30) bialkyl.
본 발명에 기재된 ‘아릴’은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 4 내지 7원, 바람직하게는 5 또는 6원을 포함하는 단일 또는 융합고리계를 포함하며, 하나 이상의 아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. 상기 아릴의 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트라이페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다. 본 발명에 기재된 ‘헤테로아릴’은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원의 단환 헤테로아릴 또는 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. 상기 헤테로아릴기는 고리 내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 상기 헤테로아릴의 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 페나진일, 페노티아진일, 페노옥사진일, 트리아졸릴, 테트라졸릴, 퓨 라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 디벤조퓨란일, 디벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 카보리닐, 페난트리딘일, 벤조디옥솔릴 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다.'Aryl' described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and includes a single or fused ring system containing 4 to 7 members, preferably 5 or 6 members, and at least one aryl It also includes structures bonded through this chemical bond. Specific examples of the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl and the like. Including but not limited to. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. 'Heteroaryl' described in the present invention includes 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. It means an aryl group which is a 5-6 membered monocyclic heteroaryl or polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. In addition, heteroaryl in the present invention also includes a structure in which one or more heteroaryl is bonded through a chemical bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl, Monocyclic heteroaryl, benzofuranyl, benzothiophenyl, such as phenazineyl, phenothiazineyl, phenooxazineyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl , Dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindoleyl, indolyl, indazolyl, benzo Polycyclic heteroaryls such as thiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, carborinyl, phenanthridinyl, benzodioxolyl and the corresponding N- Oxides (eg pyridyl N-oxide, quinolyl N-jade Id), and the like of these quaternary salts, but 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 a (C6-C20) aryl or (C6-C12) aryl. '(C3-C30) heteroaryl' group includes (C3-C20) heteroaryl or (C3-C12) heteroaryl, and the '(C3-C30) cycloalkyl' group is (C3-C20) cycloalkyl or (C3- C7) cycloalkyl. '(C2-C30) alkenyl or alkynyl' groups include (C2-C20) alkenyl or alkynyl, (C2-C10) alkenyl or alkynyl.
또한 본 발명의 ‘치환 또는 비치환된’이라는 기재에서 ‘치환’은 비치환된 치환기에 더 치환되는 경우를 뜻하며, 상기 R1 내지 R4, R11 내지 R22, R31 내지 R33, R41 내지 R48에 더 치환되는 치환기는 서로 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된(C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된(C3-C30)헤테로아릴, (C3-C30)헤테로아릴, 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시 클로알킬, 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬, NR61R62, BR63R64, PR65R66, P(=O)R67R68, R69R70R71Si-, R72Z-, R73C(=O)-, R74C(=O)O-, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성할 수 있고; 상기 R61 내지 R72는 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이며; 상기 Z는 S 또는 O이고; 상기 R73 및 R74는 서로 독립적으로 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴 또는 (C6-C30)아릴옥시를 포함한다.In addition, in the description of "substituted or unsubstituted" in the description of "substituted" means a case further substituted with an unsubstituted substituent, the R 1 to R 4 , R 11 to R 22 , R 31 to R 33 , R Substituents further substituted with 41 to R 48 independently of each other deuterium, halogen, halogen substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl substituted or unsubstituted (C3-C30) heteroaryl, (C3-C30) heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30) cyclo Alkyl, (C3-C30) cycloalkyl fused at least one aromatic ring, NR 61 R 62 , BR 63 R 64 , PR 65 R 66 , P (= O) R 67 R 68 , R 69 R 70 R 71 Si- , R 72 Z-, R 73 C (= 0)-, R 74 C (= 0) O-, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, (C6- C30) Ar (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro or hydroxy Further substituted by one or more selected from, or is the adjacent substituents may be connected to form a ring; R 61 to R 72 independently of one another are (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl; Z is S or O; R 73 and R 74 independently of one another include (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, (C 6 -C 30) aryl or (C 6 -C 30) aryloxy.
보다 구체적으로 본 발명은 하기 화합물로부터 선택되며, 이에 한정되지는 않는다. More specifically, the present invention is selected from the following compounds, but is not limited thereto.
[R1, R2 및 R51 내지 R54는 상기 화학식 1의 R1 내지 R3의 정의와 동일하다.][R 1 , R 2 and R 51 to R 54 are the same as defined in R 1 to R 3 of Chemical Formula 1.]
상기 L1 내지 L3은 서로 독립적으로 하기 구조에서 선택되며, 이에 한정되지는 않는다.L 1 to L 3 are independently selected from the following structures, but are not limited thereto.
또한 상기 R4는 수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 플루오르, 시아노, 메톡시, 에톡시, n-프로폭시, i-프로폭시, n-부톡시, i-부톡시, t-부톡시, n-펜톡시, i-펜톡시, n-헥실옥시, n-헵톡시, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 시클로헵틸, 시클로옥틸, 시클로노닐, 시클로데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 비페닐, 플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 페나진일, 페노티아진일, 페노옥사진일, 벤조퓨란일, 벤조티오펜일, 디벤조퓨란일, 디벤조티오페닐, 피라졸릴, 인돌릴, 카바졸릴, 카보리닐, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸디메틸실릴, 디메틸페닐실릴, 트리페닐실릴 또는 벤질에서 선택되며, 이에 한정되지는 않는다.And R 4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl , 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, fluorine, cyano, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t -Butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, tri Fluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl , Naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, phenazinyl, phenyl Thiazinyl, phenooxazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, carboryl, thiazolyl, oxazolyl, benzothiazolyl, Benzooxazolyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl or benzyl, but are not limited thereto.
더 바람직하게 상기 R4는 하기 구조에서 선택되며, 이에 한정되지는 않는다.More preferably, R 4 is selected from the following structures, but is not limited thereto.
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.
또한, 본 발명은 유기 전계 발광 소자를 제공하며, 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어진 유기 전계 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1의 유기 발광 화합물 하나 이상을 호스트로 하여 하나 이상의 도판트를 포함하는 것을 특징으로 한다. 본 발명의 유기 전계 발광 소자에 적용되는 도판트는 특별히 제한되지는 않으나, 본 발명의 유기 전계 발광 소자에 적용되는 도판트는 하기 화학식 2로 표시되는 화합물로부터 선택되는 것이 바람직하다.In addition, the present invention provides an organic electroluminescent device, the organic electroluminescent device according to the present invention comprises a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound of Formula 1. The organic material layer may include a light emitting layer, and the light emitting layer may include one or more dopants using at least one organic light emitting compound of Formula 1 as a host. The dopant applied to the organic electroluminescent device of the present invention is not particularly limited, but the dopant applied to the organic electroluminescent device of the present invention is preferably selected from a compound represented by the following formula (2).
[화학식 2] [Formula 2]
MM 1One LL 101101 LL 102102 LL 103103
[상기 화학식 2에서,[In Formula 2,
M1은 7족, 8족, 9족, 10족, 11족, 13족, 14족, 15족 및 16족의 금속으로 이 루어진 군으로부터 선택되고, 리간드 L101, L102 및 L103 는 서로 독립적으로 하기 구조로부터 선택되며;M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15, and 16, and ligands L 101 , L 102 and L 103. Are independently selected from the following structures;
R201 내지 R203은 서로 독립적으로 수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴 또는 할로겐이고; R204 내지 R219는 서로 독립적으로 수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알콕시, 치환 또는 비치환된(C3-C30)시클로알킬, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된 모노 또는 치환 또는 비치환된 디-(C1-C30)알킬아미노, 치환 또는 비치환된 모노 또는 디-(C6-C30)아릴아미노, SF5, 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 시아노 또는 할로겐이고; R220 내지 R223은 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬 또는 (C1-C30)알킬이 치환되거나 치환되지 않은 (C6-C30)아릴이고; R224 및 R225는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이거나, R224와 R225는 융합고리를 포함하거나 포함하지 않는 (C3-C12)알킬렌 또는 (C3-C12)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성하며; R226은 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴, 치환 또는 비치환된(C5-C30)헤테로아릴 또는 할로겐이고; R227 내지 R229는 서로 독립적으로 수소, 중수소, 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 할로겐이고;R 201 to R 203 are independently of each other hydrogen, (C1-C30) alkyl with or without halogen, (C6-C30) aryl or halogen with or without (C1-C30) alkyl; R 204 to R 219 are each independently hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or Unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono or substituted or unsubstituted di- (C1-C30) alkylamino, substituted or unsubstituted Mono or di- (C6-C30) arylamino, SF 5 , substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted Or unsubstituted tri (C6-C30) arylsilyl, cyano or halogen; R 220 to R 223 are each independently hydrogen, deuterium, (C1-C30) alkyl with or without halogen, or (C6-C30) aryl with or without (C1-C30) alkyl; R 224 and R 225 are independently of each other hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen, or R 224 and R 225 contain fused rings Linked with (C3-C12) alkylene or (C3-C12) alkenylene with or without formation to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; R 226 is substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30) heteroaryl or halogen; R 227 to R 229 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen;
Q는 , 또는 이며, R231 내지 R242는 서로 독립적으로 수소, 중수소, 할로겐이 치환되거나 치환되지 않은 (C1-C30)알킬, (C1-C30)알콕시, 할로겐, 치환 또는 비치환된(C6-C30)아릴, 시아노, 치환 또는 비치환 된(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 , or R 231 to R 242 are each independently of the other hydrogen, deuterium, (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, Cyano, substituted or unsubstituted (C5-C30) cycloalkyl, or may be linked to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring, or with R 207 or R 208 and alkylene or alkenylene To form a saturated or unsaturated fused ring.]
상기 화학식 2의 도판트 화합물은 하기 구조의 화합물로 예시될 수 있으나 이에 한정하는 것은 아니다.The dopant compound of Formula 2 may be exemplified as a compound having the following structure, but is not limited thereto.
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 1 의 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, 2, 4, 5 cycle transition metals, lanthanide series metals and organic metals of d-transition elements It may further comprise one or more metals or complex compounds selected from, the organic material layer may include a light emitting layer and a charge generating layer.
또한, 상기 유기물층에 상기 유기 발광 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다. 상기 청색, 녹색 또는 적색 발광을 하는 화합물은 한국특허출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In addition, an organic electroluminescent device that emits white light may be formed by simultaneously including one or more organic light emitting layers including blue, red, or green light emitting compounds in addition to the organic light emitting compound. The compound emitting blue, green, or red light is exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.
본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 ‘표면층’이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해, 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드로서는 예컨대 SiOx(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON 등을 바람직하게 들 수 있으며, 할로겐화 금속으로서는 예컨대 LiF, MgF2, CaF2, 불화 희토류 금속 등을 바람직하게 들 수 있으며, 금속 산화물로서는 예컨대 Cs2O, Li2O, MgO, SrO, BaO, CaO 등을 바람직하게 들 수 있 다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer on at least one inner surface of a pair of electrodes (hereinafter, these are referred to as 'surface layers'). It is preferable to arrange | position the above. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Examples of the chalcogenide include SiO x (1 ≦ X ≦ 2 ), AlO X (1 ≦ X ≦ 1.5), SiON, SiAlON, and the like, and examples of the metal halide include LiF, MgF 2 , CaF 2 , and fluoride. Rare earth metals and the like are preferable. Examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식으로, 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있다. 바람직한 환원성 도판트로서는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 도 있다.Further, in the organic electroluminescent device of the present invention, disposing a mixed region of an electron transfer compound and a reducing dopant or a mixed region of a hole transfer compound and an oxidative dopant on at least one surface of the pair of electrodes thus produced desirable. In this way, the electron transfer compound is reduced to an anion, thereby facilitating injection and transfer of electrons from the mixed region into the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transfer holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof. In addition, the reducing dopant layer The white organic electroluminescent device having two or more light emitting layers may be manufactured using the charge generating layer.
본 발명에 따른 유기 발광 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다. The organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent driving life of the device.
이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명하나, 이는 단지 그 실시 양태를 예시하기 위한 것일 뿐, 본 발명의 범위를 한정하는 것은 아니다.Hereinafter, the organic light emitting compound according to the present invention, a method for preparing the same and a light emitting property of the device are described for the detailed understanding of the present invention, but the present invention is only intended to illustrate the embodiments of the present invention. It does not limit the scope of the invention.
[제조예 1] 화합물 1의 제조Preparation Example 1 Preparation of Compound 1
화합물 compound 1-11-1 의 제조Manufacture
페닐하이드라진(phenylhydrazine) 40 g(0.36 mol), (E)-에틸-2-시아노-3-에톡시아크릴레이트((E)-ethyl 2-cyano-3-ethoxyacrylate) 62 g(0.36 mol), EtOH 400 mL를 넣고 100 ℃에서 2시간 동안 환류 교반하였다. 반응이 완결되면 회전 증발기로 EtOH를 제거 한 후 컬럼 크로마토그래피로 정제 하여 화합물 1-1 70 g(82%)을 얻었다.40 g (0.36 mol) of phenylhydrazine, 62 g (0.36 mol) of (E) -ethyl-2-cyano-3-ethoxyacrylate, 400 mL of EtOH was added and stirred under reflux at 100 ° C. for 2 hours. Upon completion of the reaction, EtOH was removed by rotary evaporation and purified by column chromatography to obtain 70 g (82%) of Compound 1-1 .
화합물 compound 1-21-2 의 제조Manufacture
화합물 1-1 30 g(0.12 mol)을 하이드라진 하이드레이트(hydrazine hydrate) 70 mL에 녹인 다음 100 ℃에서 2시간 동안 환류 교반하였다. 반응이 완결되면 온도를 실온으로 천천히 올린다. 이때 고체가 생성되는데, 이 고체를 다이에틸에테르(diethyl ether)로 세척하고 감압 여과하여 화합물 1-2 26 g(92%)을 얻었다.30 g (0.12 mol) of Compound 1-1 was dissolved in 70 mL of hydrazine hydrate, followed by stirring under reflux at 100 ° C. for 2 hours. When the reaction is complete, slowly raise the temperature to room temperature. At this time, a solid was produced. The solid was washed with diethyl ether and filtered under reduced pressure to obtain 26 g (92%) of compound 1-2 .
화합물 compound 1-31-3 의 제조Manufacture
화합물 1-2 29 g(0.13 mol)을 아세트산(acetic acid) 625 mL에 녹인 다음, 여기에 NaNO2 10.1 g(0.14 mol)를 물 70 mL에 녹인 용액을 0 ℃에서 천천히 떨어뜨린 후 15분간 교반하였다. 반응이 완결되면 고체가 생성되는데 이때 에틸아세테이트(ethyl aceacte) 500 mL를 넣고, 15분간 교반하여 고체를 녹인다. 여기에 Na2CO3 수용액으로 PH가 7이 되도록 넣어준 후 증류수로 세척하고, 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시키고, 회전 증발기로 용매를 제거한 후 에틸아세테이트를 전개 용매로 하여 컬럼 크로마토그래피로 정제하여 화합물 1-3 25 g(80%)를 얻었다. Compound 1-2 29 g (0.13 mol) was dissolved in 625 mL of acetic acid, and then a solution of 10.1 g (0.14 mol) of NaNO 2 in 70 mL of water was slowly dropped at 0 ° C, followed by stirring for 15 minutes. It was. When the reaction is completed, a solid is formed. At this time, 500 mL of ethyl acetate is added and the mixture is stirred for 15 minutes to dissolve the solid. The pH was added to 7 with Na 2 CO 3 aqueous solution, washed with distilled water, and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using ethyl acetate as a developing solvent to obtain compound 1-3 25 g (80%).
화합물 compound 1-41-4 의 제조Manufacture
질소 분위기 하에 화합물 1-3 47 g(0.20 mol), 벤질알코올(benzyl alcohol) 85 mL(0.82 mol), 자일렌 700 mL를 140 ℃에서 5시간 동안 환류 교반하였다. 반응이 완결되면, 증류수로 세척하고 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시키고 회전 증발기로 용매를 제거한 후 에틸아세테이트를 전개 용매로 하여 컬럼 크로마토그래피로 정제하여 화합물 1-4 25 g(40%)를 얻었다. 47 g (0.20 mol) of Compound 1-3 , 85 mL (0.82 mol) of benzyl alcohol, and 700 mL of xylene were stirred at reflux for 5 hours at 140 ° C. When the reaction was completed, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using ethyl acetate as a developing solvent, to obtain Compound 1-4 25 g (40%).
화합물 compound 1-61-6 의 제조Manufacture
화합물 1-4 21 g(68.06 mmol)을 EtOH 500 mL에 녹인 다음 Pd/C 10 g을 천천히 첨가하였다. H2(gas)를 흘려주면서 6시간 동안 반응한 후, 여기에 1,2-bis(4-bromophenyl)ethane-1,2-dione 25 g(68.06 mmol)를 넣고 100 ℃에서 24시간 동안 환류 교반하였다. 반응이 완결되면 회전 증발기로 EtOH를 제거하고, 증류수로 세척 한 후 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시키고 회전 증발기로 용매를 제거한 후 에틸아세테이트를 전개 용매로 하여 컬럼 크로마토그래피로 정제하여 화합물 1-5 28 g(82%)를 얻었다.21 g (68.06 mmol) of Compound 1-4 were dissolved in 500 mL of EtOH, and 10 g of Pd / C was slowly added thereto. After reacting for 6 hours while flowing H 2 (gas), 25 g (68.06 mmol) of 1,2-bis (4-bromophenyl) ethane-1,2-dione was added thereto, and the mixture was stirred under reflux at 100 ° C. for 24 hours. It was. Upon completion of the reaction, EtOH was removed with a rotary evaporator, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and purified by column chromatography using ethyl acetate as a developing solvent, to obtain Compound 1-5 28 g (82%).
화합물 compound 1One 의 제조Manufacture
화합물 1-5 3 g(5.92 mmol), 카바졸(carbazole) 2.5 g(14.8 mmol), Pd(dba)3 270 mg(0.2 mmol), Dave-phos 230 mg(0.5 mol) 및 Naot-Bu 1.7 g(17.7 mmol)를 톨루엔 100 mL에 녹이고, 120 ℃에서 24시간 동안 환류 교반하였다. 반응이 완결되면 회전 증발기로 EtOH를 제거하고, 증류수로 세척한 후 에틸아세테이트로 추출하였다. 유기층을 MgSO4로 건조시키고 회전 증발기로 용매를 제거한 후 에틸아세테이트를 전개 용매로 하여 컬럼 크로마토그래피로 정제하여 화합물 1 3 g(75%)를 얻었다.Compound 1-5 3 g (5.92 mmol), carbazole 2.5 g (14.8 mmol), Pd (dba) 3 270 mg (0.2 mmol), Dave-phos 230 mg (0.5 mol) and Naot-Bu 1.7 g (17.7 mmol) was dissolved in 100 mL of toluene and stirred at reflux at 120 ° C. for 24 hours. Upon completion of the reaction, EtOH was removed with a rotary evaporator, washed with distilled water and extracted with ethyl acetate. The organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and purified by column chromatography using ethyl acetate as a developing solvent, to obtain Compound 1 (3 g, 75%).
[제조예 2] 화합물 37의 제조Preparation Example 2 Preparation of Compound 37
화합물 compound 2-12-1 의 제조Manufacture
카바졸(carbazole) 20 g(119.6 mmol), 1,4-다이브로모벤젠(1,4-dibromobenzene) 56.4 g(239.2 mmol), Cu 11.4 g(178.4 mmol), K2CO3 49 g(358.8 mmol) 및 18-crown-6 6.3 g(23.92 mmol)을 1,2-다이클로로벤젠(1,2-dichlorobenzene) 400 mL에 녹인 다음 200 ℃에서 20시간 동안 가열하였다. 감압 증류하고 EA로 추출한 후, 증류수로 세척하고 MgSO4로 건조하였다. 감압 증류하고 컬럼 분리하여 화합물 2-1 18 g(55.86 mmol, 46.94%) 을 얻었다. 20 g (119.6 mmol) of carbazole, 56.4 g (239.2 mmol) of 1,4-dibromobenzene, 11.4 g (178.4 mmol) of Cu, 49 g (358.8 mmol) of K 2 CO 3 ) And 18-crown-6 6.3 g (23.92 mmol) were dissolved in 400 mL of 1,2-dichlorobenzene and heated at 200 ° C. for 20 hours. After distillation under reduced pressure and extraction with EA, the mixture was washed with distilled water and dried over MgSO 4 . Distillation under reduced pressure and column separation yielded Compound 2-1 18 g (55.86 mmol, 46.94%).
화합물 compound 2-22-2 의 제조Manufacture
화합물 2-1 18 g(55.86 mmol)을 THF 200 mL에 녹이고 -78 ℃에서 n-buLi 24.58 mL(61.45 mmol, 2.5M in Hexane)을 천천히 넣었다. 1시간 후 DMF 5.6 mL(72.65 mmol)을 넣고, 12시간 동안 상온에서 교반하였다. 증류수를 넣고 EA로 추출한 후, MgSO4로 건조하고 감압 증류하였다. 컬럼 분리하여 화합물 2-2 11 g(40.54 mmol, 72.58%)을 얻었다. 18 g (55.86 mmol) of Compound 2-1 were dissolved in 200 mL of THF, and 24.58 mL (61.45 mmol, 2.5M in Hexane) of n-buLi was slowly added at -78 ° C. After 1 hour, 5.6 mL (72.65 mmol) of DMF was added thereto, followed by stirring at room temperature for 12 hours. Distilled water was added and extracted with EA, dried over MgSO 4 and distilled under reduced pressure. Compound 2-2 11 g (40.54 mmol, 72.58%) was obtained by column separation.
화합물 compound 2-32-3 의 제조Manufacture
화합물 2-2 11 g(40.54 mmol), 5-브로모피리딘-2,3-다이아민(5-bromopyridine-2,3-diamine) 7.6 g(40.54 mmol)을 DMSO 200 mL에 녹인 다음, 200 ℃에서 12시간 동안 가열하였다. 상온으로 냉각한 후 증류수로 세척하고 EA로 추출하였다. MgSO4로 건조하고 감압 증류한 후 컬럼 분리 하여 화합물 2-3 5 g(11.38 mmol, 28.07%) 을 얻었다. 11 g (40.54 mmol) of Compound 2-2 and 7.6 g (40.54 mmol) of 5-bromopyridine-2,3-diamine were dissolved in 200 mL of DMSO, followed by 200 ° C. Heated at for 12 h. After cooling to room temperature, washed with distilled water and extracted with EA. Drying with MgSO 4 , distillation under reduced pressure and column separation yielded Compound 2-3 (5 g, 11.38 mmol, 28.07%).
화합물 compound 2-42-4 의 제조Manufacture
화합물 2-3 5 g(11.38 mmol), 아이오도벤젠(iodobenzene) 2.53 mL(22.76 mmol), Cu 1.08 g(17.07 mmol), K2CO3 4.7 g(34.11 mmol) 및 18-crown-6 0.3 g(1.13 mmol)을 1,2-다이클로로벤젠(1,2-dichlorobenzene) 100 mL에 녹인 다음 200 ℃에서 20시간 동안 가열하였다. 감압 증류하고 EA로 추출한 후 증류수로 세척하고 MgSO4로 건조하였다. 감압 증류하고 컬럼 분리하여 화합물 2-4 3 g(5.82 mmol, 51.14%)을 얻었다. Compound 2-3 5 g (11.38 mmol), 2.53 mL (22.76 mmol) of iodobenzene, 1.08 g (17.07 mmol) Cu, 4.7 g (34.11 mmol) K 2 CO 3 and 0.3 g 18-crown-6 (1.13 mmol) was dissolved in 100 mL of 1,2-dichlorobenzene and heated at 200 ° C. for 20 hours. Distillation under reduced pressure, extraction with EA, washing with distilled water and drying with MgSO 4 were performed. Distillation under reduced pressure and column separation yielded 3 g (5.82 mmol, 51.14%) of compound 2-4 .
화합물 compound 3737 의 제조Manufacture
화합물 2-4 3 g(5.80 mmol), 페닐보론산(phenylboronic acid) 1.06 g(8.73 mmol), Pd(PPh3)4 0.20 g(0.17 mmol), 2M K2CO3 6 mL, 톨루엔 50 mL 및 에탄올 20 mL 을 혼합한 후 6시간 동안 환류 교반하였다. 상온으로 냉각하고 증류수로 세척한 후 EA로 추출하였다. MgSO4로 건조하고 감압 증류한 후, 컬럼 분리하여 화합물 37 2.5 g(4.87 mmol, 84.08%) 을 얻었다. Compound 2-4 3 g (5.80 mmol), phenylboronic acid 1.06 g (8.73 mmol), Pd (PPh 3 ) 4 0.20 g (0.17 mmol), 2M K 2 CO 3 6 mL, 50 mL toluene and 20 mL of ethanol were mixed and stirred under reflux for 6 hours. Cooled to room temperature, washed with distilled water and extracted with EA. After drying over MgSO 4 , distillation under reduced pressure, and column separation to obtain compound 37 2.5 g (4.87 mmol, 84.08%).
상기 제조예 1 및 제조예 2의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 52를 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to 52 were prepared using the methods of Preparation Example 1 and Preparation Example 2, and 1 H NMR and MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.
[표 1]TABLE 1
[실시예 1] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 1 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention
본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15 Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 4,4',4"-tris(N,N- (2-naphthyl)-phenylamino)triphenylamine (2-TNATA)을 넣고, 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 2-TNATA를 증발시켜 ITO 기판 상에 60 nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명에 따른 화합물 1을 넣고, 또 다른 셀에는 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 4 내지 10%중량으로 도핑함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자전달층으로써 tris(8-hydroxyquinoline)-aluminum(Ⅲ) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 lithium quinolate (Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED소자를 제작하였다. An OLED device having a structure using the light emitting material of the present invention was produced. First, a transparent electrode ITO thin film (15? It was used after. Next, the ITO substrate is installed in the substrate folder of the vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2-TNATA) is installed in the cell in the vacuum deposition apparatus. And evacuated until the vacuum in the chamber reached 10 −6 torr, followed by applying a current to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate. N, N '-bis (α- naphthyl) - N, N' to another cell of the vapor deposition devices placed -diphenyl-4,4'-diamine (NPB) , and evaporation of the NPB by applying a current to the cell, the hole injection layer A hole transport layer having a thickness of 20 nm was deposited on top of the layer, after which the hole injection layer and the hole transport layer were formed, a light emitting layer was deposited thereon as follows: Compound 1 according to the present invention was used as a host in one cell in a vacuum deposition apparatus. put, and then in the other cell as a dopant into the Ir (ppy) 3 [tris ( 2-phenylpyridine) iridium] , respectively, the two materials at different rates A light emitting layer of 30 nm thickness was deposited on the hole transport layer by flashing and doping at 4 to 10% by weight, followed by 20 nm thick tris (8-hydroxyquinoline) -aluminum (III) (Alq) as an electron transporting layer on the light emitting layer. After depositing, the lithium quinolate (Liq) was deposited with an electron injection layer to a thickness of 1 to 2 nm, and an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device.
재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 OLED 발광재료로 사용하였다.Each compound was vacuum sublimated and purified under 10 -6 torr to be used as an OLED light emitting material.
그 결과, 6.4 V의 전압에서 4.1 mA/cm2의 전류가 흘렀으며, 1190 cd/m2의 녹색발광이 확인되었다.As a result, a current of 4.1 mA / cm 2 flowed at a voltage of 6.4 V, and green light emission of 1190 cd / m 2 was confirmed.
[실시예 2] [Example 2]
발광층에서 호스트 재료로서 화합물 3을 넣고, 발광 도판트로서 (piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate]을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.OLED device in the same manner as in Example 1, except that Compound 3 was added as a host material in the light emitting layer and (piq) 2 Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] was used as the light emitting dopant. Was produced.
그 결과, 7.0 V의 전압에서 13.4 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 적색발광이 확인되었다.As a result, a current of 13.4 mA / cm 2 flowed at a voltage of 7.0 V, and red light emission of 1000 cd / m 2 was observed.
[실시예 3] Example 3
발광층에서 호스트 재료로서 화합물 26을 넣고, 발광 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]을 이용한 것 외에는, 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was manufactured in the same manner as in Example 1, except that Compound 26 was added as a host material in the emission layer and Ir (ppy) 3 [tris (2-phenylpyridine) iridium] was used as the emission dopant.
그 결과, 7.0 V의 전압에서 4.1 mA/cm2의 전류가 흘렀으며, 1120 cd/m2의 녹색발광이 확인되었다.As a result, a current of 4.1 mA / cm 2 flowed at a voltage of 7.0 V, and green light emission of 1120 cd / m 2 was confirmed.
[비교예 1] Comparative Example 1
진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 4,4'-bis(carbazol-9-yl)biphenyl(CBP), 도판트로서 Ir(ppy)3[tris(2-phenylpyridine)iridium]을 이용하고, 정공차단층으로 비스(2-메틸-8-퀴놀리네이토)(p-페닐페놀레이토)알루미늄(Ⅲ) (BAlq)를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.4,4'-bis (carbazol-9-yl) biphenyl (CBP) as a host material in one cell in the vacuum deposition equipment, Ir (ppy) 3 as a dopant [tris (2-phenylpyridine) iridium] OLED device in the same manner as in Example 1, except that bis (2-methyl-8-quinolinate) ( p -phenylphenolrato) aluminum (III) (BAlq) was used as the hole blocking layer. Was produced.
그 결과, 7.5 V의 전압에서 3.8 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 녹색발광이 확인되었다.As a result, a current of 3.8 mA / cm 2 flowed at a voltage of 7.5 V, and green light emission of 1000 cd / m 2 was confirmed.
[비교예 2] Comparative Example 2
진공 증착 장비 내의 한쪽 셀에 호스트 재료로서 본 발명의 화합물 대신 4,4'-bis(carbazol-9-yl)biphenyl (CBP), 도판트로서 (piq)2Ir(acac)[bis-(1-phenyl4,4'-bis (carbazol-9-yl) biphenyl (CBP), as a dopant (piq) 2 Ir (acac) [bis- (1- phenyl
isoquinolyl)iridium(Ⅲ)acetylacetonate]을 이용하고, 정공차단층으로 비스(2-메틸-8-퀴놀리네이토)(p-페닐페놀레이토)알루미늄(Ⅲ) (BAlq)를 사용한 것을 제외하고는 실시예 6과 동일한 방법으로 OLED소자를 제작하였다.isoquinolyl) iridium (III) acetylacetonate], except that bis (2-methyl-8-quinolinate) ( p -phenylphenolrato) aluminum (III) (BAlq) was used as the hole blocking layer. An OLED device was manufactured in the same manner as in Example 6.
그 결과, 7.5 V의 전압에서 15.3 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 적색발광이 확인되었다.As a result, a current of 15.3 mA / cm 2 flowed at a voltage of 7.5 V, and red light emission of 1000 cd / m 2 was confirmed.
본 발명에서 개발한 유기 발광 화합물들은 그 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 발광 화합물을 발광용 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있었다.The organic light emitting compounds developed in the present invention was confirmed that the luminescent properties are superior to the conventional material. In addition, the device using the organic light emitting compound according to the present invention as a light emitting host material was not only excellent in the light emission characteristics, but also by lowering the driving voltage to increase the power efficiency to improve the power consumption.
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WO (1) | WO2011055911A1 (en) |
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JP2001284049A (en) * | 2000-03-31 | 2001-10-12 | Fuji Photo Film Co Ltd | Color conversion membrane and light emitting device using it |
JP4344494B2 (en) * | 2000-08-24 | 2009-10-14 | 富士フイルム株式会社 | Light emitting device and novel polymer element |
CA2677661A1 (en) * | 2007-02-07 | 2008-08-14 | Kyowa Hakko Kirin Co., Ltd. | Tricyclic compounds |
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2009
- 2009-11-04 KR KR1020090106135A patent/KR20110049217A/en not_active Application Discontinuation
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2010
- 2010-10-05 WO PCT/KR2010/006796 patent/WO2011055911A1/en active Application Filing
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US8920946B2 (en) | 2012-06-29 | 2014-12-30 | Samsung Display Co., Ltd. | Organic light-emitting compound and organic light-emitting device including the same |
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WO2011055911A1 (en) | 2011-05-12 |
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