KR101741415B1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the sameDownload PDFInfo
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- KR101741415B1 KR101741415B1KR1020090037505AKR20090037505AKR101741415B1KR 101741415 B1KR101741415 B1KR 101741415B1KR 1020090037505 AKR1020090037505 AKR 1020090037505AKR 20090037505 AKR20090037505 AKR 20090037505AKR 101741415 B1KR101741415 B1KR 101741415B1
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Abstract
Translated fromKorean
Description
Translated fromKorean본 발명은 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 본 발명에 따른 유기 발광 화합물은 유기 발광 소자의 전자전달층에 포함될 수 있다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device employing the same. More particularly, the organic electroluminescent compound according to the present invention can be included in an electron transport layer of an organic light emitting device.
표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있으며, 1987년 이스트만 코닥(Eastman Kodak)사에서는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast and fast response speed. In 1987, Eastman Kodak Co., An organic EL device using an aromatic diamine and an aluminum complex having a low molecular weight as a material for forming a light emitting layer has been developed for the first time [Appl. Phys. Lett. 51, 913, 1987].
유기 EL 소자는 전자 주입 전극(음극) 과 정공 주입 전극(양극) 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸하면서 빛을 내는 소자이다. 플라스틱 같은 휠 수 있는(flexible) 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널(Plasma Display Panel)이나 무기 EL 디스플레이에 비해 낮은 전압에서 (10V이하) 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있다.An organic EL device is a device that injects electric charge into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to form an electron and a hole. It is possible to form a device on a flexible transparent substrate such as a plastic substrate. Further, the device can be driven at a lower voltage (10 V or less) than a plasma display panel or an inorganic EL display, It has the advantage of being excellent in color.
유기 EL 소자에서 유기재료는 크게 발광재료와 전하수송재료로 나눌 수 있다. 발광재료는 발광색 및 발광효율에 직접적으로 관계가 있는데, 요구되는 몇 가지 특성으로는 고체 상태에서 형광 양자 수율이 커야하고, 전자와 정공의 이동도가 높아야 하며, 진공 증착 시 쉽게 분해되지 않아야 하고, 균일한 박막을 형성, 안정해야한다.In an organic EL device, an organic material can be largely divided into a light emitting material and a charge transporting material. The luminescent material is directly related to the luminescent color and the luminescent efficiency. Some required characteristics are that the luminescent quantum yield in the solid state must be high, the electron and hole mobility must be high, the luminescent material should not be easily decomposed in the vacuum deposition, A uniform thin film should be formed and stabilized.
한편, 기존 전자 전달 재료의 대표적인 예로는, 1987년 Kodak이 발표한 다층박막 OLED 이전부터 사용되어진 tris(8-hydroxyquinoline)aluminum(III) (Alq)과 같은 알루미늄 착체와 1990년대 중반 일본에서 발표되었던 bis(10-hydroxybenzo- [h]quinolinato)beryllium (Bebq)과 같은 베릴륨 착체(Bebq)[T. Sato et.al.J. Mater. Chem. 10 (2000) 1151] 등이 있다. 그러나, 이들 재료의 경우, 그 한계가 2002년 이후로 OLED가 상용화되면서 대두되기 시작하였고, 이후로 고성능의 전자 전달 재료가 다수 연구 발표되어, 상용화에 근접하게 되었다.Typical examples of conventional electron transfer materials include aluminum complexes such as tris (8-hydroxyquinoline) aluminum (III) (Alq) used before Kodak's multilayer thin film OLED in 1987 and bis (Bebq) such as 10-hydroxybenzo- [h ] quinolinato beryllium (Bebq) [T. Sato et al.J. Mater. Chem. 10 (2000) 1151). However, in the case of these materials, since the OLED has been commercialized since 2002, the limit has begun to emerge. Since then, a number of high-performance electron-transporting materials have been studied and commercialized.
한편, 비 금속착체 계열로, 현재까지 발표된 좋은 특성의 전자 전달재료로는spiro-PBD[N. Johansson et.al.Adv. Mater.10 (1998) 1136], PyPySPyPy[M. Uchida et.al.Chem. Mater. 13 (2001) 2680] 및 Kodak의 TPBI[Y.-T. Tao et.al. Appl. Phys. Lett. 77 (2000) 1575] 등이 있으나, 전기 발광 특성 및 수명 측면에서 아직 많은 개선의 여지가 남아 있다.On the other hand, as non-metal complex series, the electron transfer materials of good characteristics that have been published so far includespiro- PBD [N. Johansson et al.Adv. Mater. 10 (1998) 1136], PyPySPyPy [M. Uchida et al.Chem. Mater. 13 (2001) 2680; and Kodak's TPBI [Y.-T. Tao et al.Appl. Phys. Lett. 77 (2000) 1575). However, there is still room for improvement in terms of electroluminescence characteristics and life span.
종래의 전자 전달 재료에 있어서, 특히 주목할 만한 것은 발표하는 내용 대비 실제로 단순히 구동 전압만을 약간 개선한다거나, 소자 구동 수명의 현저한 저하 등의 문제점들을 보이고 있고, 컬러별 소자 수명의 편차 및 열적 안정성 저하 등의 부작용적 특성을 나타낸다는 것이다. 현재까지 OLED 패널의 대형화에 걸림돌로 작용하고 있는 소비 전력, 휘도의 증가 등 목표를 달성하기 위해서는 상기의 부작용적 특성들은 큰 장애가 되고 있는 게 현실이라고 하겠다.Particularly noteworthy in the conventional electron transferring material is that the driving voltage is merely slightly improved or the driving life of the device is remarkably lowered compared to the contents to be announced. Side effects. In order to achieve the target such as power consumption and brightness increase which are obstacles to the enlargement of OLED panel up to now, it is a reality that the above-mentioned side effects are a big obstacle.
따라서 본 발명의 목적은 상기한 문제점들을 해결하기 위하여 기존의 전자전달재료보다 발광 효율, 소비 전력 및 소자 수명이 좋은 우수한 골격의 유기 발광 화합물을 제공하는 것이며, 신규한 유기 발광 화합물을 전자전달층에 채용하는 유기 전계 발광 소자를 제공하는 것이다.Accordingly, an object of the present invention is to provide an organic light emitting compound having an excellent skeleton which is superior in luminous efficiency, power consumption, and device life to an existing electron transporting material in order to solve the above problems, And an organic electroluminescent device employing the same.
본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자에 관한 것으로, 본 발명에 따른 유기 발광 화합물은 유기 전계 발광 소자의 전자전달층에 포함되어 소자의 구동 전압을 낮춤으로서 발광효율 및 소비 전력을 현저히 감소시킬 수 있는 장점이 있다.The present invention relates to an organic light emitting compound represented by the following general formula (1) and an organic electroluminescent device employing the same. The organic electroluminescent compound according to the present invention is contained in an electron transport layer of an organic electroluminescent device, There is an advantage that the luminous efficiency and the power consumption can be remarkably reduced.
본 발명은 하기 화학식 1의 유기 발광 화합물을 제공한다.The present invention provides an organic luminescent compound represented by the following general formula (1).
[화학식 1][Chemical Formula 1]
[상기 화학식 1에서,[In the above formula (1)
L은 화학결합이거나, 치환 또는 비치환된 (C6-C30)아릴렌, 치환 또는 비치환 된 (C3-C30)헤테로아릴렌, 치환 또는 비치환된 5원 내지 7원의 헤테로시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬렌,치환 또는 비치환된(C3-C30)시클로알킬렌, 치환 또는 비치환된 방향족고리가 하나이상 융합된 (C3-C30)시클로알킬렌, 치환 또는 비치환된 아다만틸렌, 치환 또는 비치환된 (C7-C30)바이시클로알킬렌, 치환 또는 비치환된(C2-C30)알케닐렌, 치환 또는 비치환된(C2-C30)알키닐렌, 치환 또는 비치환된(C6-C30)아르(C1-C30)알킬렌, 치환 또는 비치환된(C1-C30)알킬렌티오, 치환 또는 비치환된(C1-C30)알킬렌옥시, 치환 또는 비치환된(C6-C30)아릴렌옥시, 치환 또는 비치환된(C6-C30)아릴렌티오, -O- 또는 -S-이고;L is a chemical bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (C3-C30) heteroarylene, a substituted or unsubstituted 5 to 7 membered heterocycloalkylene, a substituted Or a 5- to 7-membered heterocycloalkylene in which at least one unsubstituted aromatic ring is fused, Substituted or unsubstituted (C3-C30) cycloalkylene, (C3-C30) cycloalkylene in which one or more substituted or unsubstituted aromatic rings are fused, substituted or unsubstituted adamantylene, substituted or unsubstituted (C2-C30) alkynylene, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkylene, substituted or unsubstituted (C2-C30) alkenylene, substituted or unsubstituted Substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C1-C30) alkylene, substituted or unsubstituted (C6-C30) arylenethio, -O- or -S-;
R1 내지 R4, Ar1 및 Ar2는 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, 치환 또는 비치환된 아다만틸, 치환 또는 비치환된(C7-C30)바이시클로알킬, 시아노, NR11R12, BR13R14, PR15R16, P(=O)R17R18[R11 내지 R18은 서로 독립적으로 치환 또는 비치환된(C1-C30)알킬, 치환 또는 비치환된(C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이다.], 치환 또는 비치환된 트리(C1-C30)알킬실릴, 치환 또는 비치환된 디(C1-C30)알킬(C6-C30)아릴실릴, 치환 또는 비치환된 트리(C6-C30)아릴실릴, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, 치환 또는 비치환된(C1-C30)알킬옥시, 치환 또는 비치환된(C1-C30)알킬티오, 치환 또는 비치환된(C6-C30)아릴옥시, 치환 또는 비치환된(C6-C30)아릴티오, 치환 또는 비치환된(C1-C30)알콕시카보닐, 치환 또는 비치환된(C1-C30)알킬카보닐, 치환 또는 비치환된(C6-C30)아릴카보닐, 치환 또는 비치환된(C2-C30)알케닐, 치환 또는 비치환된(C2-C30)알키닐, 치환 또는 비치환된(C6-C30)아릴옥시카보닐, 치환 또는 비치환된(C1-C30)알콕시카보닐옥시, 치환 또는 비치환된(C1-C30)알킬카보닐옥시, 치환 또는 비치환된(C6-C30)아릴카보닐옥시, 치환 또는 비치환된(C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로,
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,W is- (CR 41 R 42) m -, - (R 41) C = C (R 42) -, -N (R 43) -, -S-, -O-, -Si (R 44) (R45) -, -P (R 46 ) -, -P (= O) (R 47) -, -C (= O) - or -B (R48) -, and
X는 각각 독립적으로 O, S, NR5이며;Each X is independently O, S, NR5 ;
R5, R31 내지 R33및 R41 내지 R48은 상기 R1 내지 R4, Ar1 및 Ar2의 정의와 동일 하고;R5 , R31 to R33, and R41 to R48 are the same as defined above for R1 to R4 , Ar1 and Ar2 ;
상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하며;Wherein said heterocycloalkyl and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P;
m은 1 또는 2의 정수이다.]and 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 포함한다.Substituents comprising " alkyl ", " alkoxy " and other " alkyl " moieties described in the present invention include both straight chain and branched forms.
본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다.&Quot; Aryl " in the present invention means an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and is a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms, And includes a form in which a plurality of aryls are connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, crycenyl, naphthacenyl, fluoranthenyl, But is not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl includes 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl.
본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화 될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연결된 형태도 포함한다. 상기 헤테로아릴기는 고리 내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페난트리딘일, 벤조디옥솔릴 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다.The "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 skeletal atoms and the remaining aromatic ring skeletal atoms are carbon Means a 5 to 6 membered monocyclic heteroaryl and a polycyclic heteroaryl condensed with at least one benzene ring and may be partially saturated. The heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected to a single bond. The heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring are oxidized or trisubstituted to form, for example, an N-oxide or a quaternary salt. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetra Monocyclic heteroaryl such as pyrrolyl, pyrrolyl, pyrrolyl, pyrrolyl, pyrrolyl, pyrrolyl, pyrrolyl, pyrazinyl, pyrrolyl, pyrrolyl, pyrazinyl, pyrimidinyl, pyridazinyl, Benzyloxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl (Such as pyridyl N-oxide, quinolyl N-oxide), quaternary salts thereof, and the like, and the like, but are not limited thereto .
또한, 본 발명에 기재되어 있는 “(C1-C30)알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C1-C30)알킬옥시카보닐, (C1-C30)알킬카보닐, (C1-C30)알킬옥시카보닐옥시, (C1-C30)알킬카보닐옥시” 등의 알킬은 탄소수 1 내지 20개로 제한될 수 있고, 탄소수 1 내지 10개로 제한될 수 있다. “(C6-C30)아릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, (C6-C30)아르(C1-C30)알킬, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C6-C30)아릴카보닐, (C6-C30)아릴옥시카보닐, (C6-C30)아릴카보닐옥시, (C6-C30)아릴옥시카보닐옥시”등의 아릴은 탄소수 6 내지 20 개로 제한될 수 있고, 탄소수 6 내지 12개로 제한될 수 있다. “(C3-C30)헤테로아릴”의 헤테로아릴은 탄소수 4 내지 20개로 제한될 수 있고, 탄소수 4 내지 12개로 제한될 수 있다. “(C3-C30)시클로알킬”의 헤테로아릴은 탄소수 3 내지 20개로 제한될 수 있고, 탄소수 3 내지 7개로 제한될 수 있다. “(C2-C30)알케닐 또는 알키닐”의 알케닐 또는 알키닐은 탄소수 2 내지 20개로 제한될 수 있고, 탄소수 2 내지 10개로 제한될 수 있다.(C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C6- (C1-C30) alkyloxycarbonyl, (C1-C30) alkyloxycarbonyl, (C1-C30) alkylthio, C1-C30) alkylcarbonyloxy "and the like may be limited to a carbon number of 1 to 20, and may be limited to a carbon number of 1 to 10. (C6-C30) aryl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) aryloxycarbonyloxy, (C6-C30) arylthio, (C6-C30) arylcarbonyl, Quot; and the like can be limited to 6 to 20 carbon atoms, and may be limited to 6 to 12 carbon atoms. The heteroaryl of " (C3-C30) heteroaryl " may be limited to from 4 to 20 carbon atoms and may be limited to from 4 to 12 carbon atoms. The heteroaryl of the "(C3-C30) cycloalkyl" may be limited to 3 to 20 carbon atoms and may be limited to 3 to 7 carbon atoms. The alkenyl or alkynyl of " (C2-C30) alkenyl or alkynyl " may be limited to from 2 to 20 carbon atoms and may be limited to from 2 to 10 carbon atoms.
또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재는 각각 독립적으로 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴이 치환 또는 비치환된 (C3-C30)헤테로아릴, B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상을 포함하는 5원 내지 7원의 헤테로시클로알킬, 방향족고리가 하나이상 융합된 5원 내지 7원의 헤테로시클로알킬, (C3-C30)시클로알킬, 방향족고리가 하나이상 융합된 (C6-C30)시클로알킬, 트리(C1-C30)알킬실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, 트리(C6-C30)아릴실릴, 아다만틸, (C7-C30)바이시클로알킬, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, 카바졸릴, NR21R22, BR23R24, PR25R26, P(=O)R27R28[R21 내지 R28은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴 또는 (C3-C30)헤테로아릴이다.], (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, (C1-C30)알킬옥시, (C1-C30)알킬티오, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C1-C30)알콕시카보닐, (C1-C30)알킬카보닐, (C6-C30)아릴카보닐, (C6-C30)아릴옥시카보닐, (C1-C30)알콕시카보닐옥시, (C1-C30)알킬카보닐옥시, (C6-C30)아릴카보 닐옥시, (C6-C30)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택된 하나 이상으로 더 치환되거나, 서로 인접한 치환체가 연결되어 고리를 형성하는 것을 의미한다.The term " substituted or unsubstituted " in the present invention is independently selected from the group consisting of deuterium, halogen, (C1-C30) alkyl substituted or unsubstituted with halogen, (C6- A 5- to 7-membered heterocycloalkyl containing at least one selected from the substituted or unsubstituted (C3-C30) heteroaryl, B, N, O, S, P (= O), Si and P, (C3-C30) cycloalkyl, (C6-C30) cycloalkyl, (C1-C30) alkylsilyl, di (C1-C30) (C2-C30) alkenyl, (C2-C30) alkynyl, (C2-C30) alkynyl, cyano,carbazolyl, NR 21 R 22, BR 23 R 24, PR 25 R 26, P (= O) R 27 R 28 [R 21 to R28 are independently selected from (C1-C30) each alkyl, (C6- (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30) alkylthio, (C6-C30) arylcarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxy, nitro, or hydroxy, or adjacent substituents are connected to form a ring.
상기 L은 화학결합이거나, 페닐렌, 나프틸렌, 안트라세닐렌, 비페닐렌, 플루오레닐렌, 트리페닐레닐렌, 플루오란테닐렌, 크리세닐렌, 터페닐렌, 페난트릴렌, 피레닐렌, 퍼릴레닐렌, 인데노플루오렌 등의 아릴렌, 피리디닐렌, 피라지닐렌, 퓨릴렌, 티에닐렌, 셀레노페닐렌, 퀴놀리닐렌, 퀴녹살리닐렌, 페난트롤리닐렌, 인돌로[3,2-b]카바졸 등의 헤테로아릴렌, 시클로펜틸렌, 시클로헥실렌, 시클로헵틸렌, 시클로옥틸렌 등의 시클로알킬렌, -O- 또는 -S-로부터 선택되어지나, 이에 한정되는 것은 아니며, 상기 화학식 1에서와 같이 더 치환될 수 있다.Wherein L is a chemical bond or a group selected from the group consisting of phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylenylene, fluoranthenylene, clreshenylene, terphenylene, phenanthrylene, pyrenylene, Examples of the aryl group include an aryl group such as phenyl, naphthyl, naphthyl, naphthyl, naphthyl, naphthyl, naphthyl, cycloalkylene such as cyclopentylene, cyclohexylene, cycloheptylene and cyclooctylene, -O- or -S-, but is not limited thereto, and examples thereof include, but are not limited to, Can be further substituted as shown in Formula 1 above.
상기 R1 내지 R5, R31 내지 R33및 R41 내지 R48은 서로 독립적으로 수소, 중수소, 할로겐, 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 에틸헥실, 헵틸, 옥틸 등의 알킬, 페닐, 나프틸, 플루오레닐, 바이페닐, 페난트릴, 터페닐, 피레닐, 퍼릴레닐, 스피로바이플루오레닐, 플루오란테닐, 크리세닐, 트리페닐레닐 등의 아릴, 시아노, 트리메틸실리, 트리에틸실릴, 디메틸에틸실릴, 트리부틸실릴 등의 트리알킬실릴, 디메틸페닐실릴 등의 디알킬아릴실릴 또는 트리페닐실릴, 트리나프틸실릴 등의 트리아릴실릴로부터 선택되어지나, 이에 한정되는 것은 아니며, 상기 화학식 1에서와 같이 더 치환될 수 있다.R1 to R5 , R31 to R33 and R41 to R48 independently represent hydrogen, deuterium, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, Aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl and triphenylenyl, cyano, trimethylsilyl , Trialkylsilyl such as triethylsilyl, dimethylethylsilyl and tributylsilyl, dialkylarylsilyl such as dimethylphenylsilyl or triarylsilyl such as triphenylsilyl and trinaphthylsilyl, but is limited to And can be further substituted as in the above formula (1).
상기 Ar1 및 Ar2는 서로 독립적으로 수소, 중수소, 할로겐, 메틸, 에틸, 프 로필, 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,
또한, 상기
[R41 내지 R48은 각각 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴 또는 치환 또는 비치환된(C3-C30)헤테로아릴이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있다.]Wherein R41 to R48 are each independently a substituted or unsubstituted (C 1 -C 30) alkyl, a substituted or unsubstituted (C 6 -C 30) aryl or a substituted or unsubstituted (C 3 -C 30) heteroaryl, (C3-C30) kylene or (C3-C30) alkenylene which may or may not contain a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.
본 발명에 따른 유기 발광 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있으나, 하기 화합물이 본 발명을 한정하는 것은 아니다.The organic luminescent compound according to the present invention may be more specifically exemplified as the following compounds, but the following compounds are not intended to limit the present invention.
본 발명에 따른 유기 발광 화합물은 하기 반응식 1에 나타난 바와 같이, 제조될 수 있다.The organic luminescent compound according to the present invention can be prepared as shown in the following Reaction Scheme 1.
[반응식 1][Reaction Scheme 1]
[상기 반응식 1에서 L, Ar1 및 Ar2, X, R1 내지 R4는 상기 화학식 1에서의 정의와 동일하다.][L, Ar1 and Ar2 , X and R1 to R4 in the above Reaction Scheme 1 are the same as defined in the above formula 1]
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 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물을 하나 이상 포함하는 것을 특징으로 한다. 상기 유기 발광 화합물은 전자전달층의 재료로 사용되어진다.The present invention provides an organic electroluminescent device, wherein 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 comprises at least one organic light emitting compound of Formula 1. The organic luminescent compound is used as a material for the electron transport layer.
또한, 상기 유기물층은 상기 화학식 1의 유기 발광 화합물이 포함된 층 하나 이상과 형광호스트, 형광도판트 또는 인광호스트, 인광도판트로 이루어진 층을 하나이상 포함하는 것을 특징으로 하며, 본 발명의 유기 전계 발광 소자에 적용되는 형광호스트, 형광도판트, 인광호스트 또는 인광도판트는 특별히 제한되지는 않는다.The organic material layer may include one or more layers including the organic light emitting compound of Formula 1 and a layer comprising a fluorescent host, a fluorescent dopant, a phosphorescent host, and a phosphorescent dopant. The organic electroluminescent layer The fluorescent host, fluorescent dopant, phosphorescent host or phosphorescent dopant applied to the device is not particularly limited.
본 발명의 유기 전계 발광 소자는 상기 화학식 1의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로 부터 선택된 하나 이상의 화합물을 포함할 수 있으며, 상기 아릴아민계 화합물 또는 스티릴아릴아민계 화합물은 출원번호 제 10-2008-0123276호, 제 10-2008-0107606호 또는 제 10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다.The organic electroluminescent device of the present invention may include at least one compound selected from the group consisting of an arylamine compound and a styrylarylamine compound, Compounds or styrylarylamine-based compounds are exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 발광 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 상기 유기물층은 발광층 이외에 전하생성층을 동시에 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in addition to the organic luminescent compound of Formula 1, an organic electroluminescent compound of group 1, group 2, group 4, periodic transition metal, group of lanthanide metal and group of d- , And the organic material layer may include a charge generation layer in addition to the light emitting layer.
또한, 상기 유기물층에 화학식 1의 유기발광 화합물 이외에 청색, 녹색 또는 적색 발광을 하는 유기 화합물층 하나 이상을 동시에 포함하여 백색 유기 전계 발광 소자를 형성할 수 있으며, 상기 청색, 녹색 또는 적색 발광을 하는 화합물은 출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다.In addition, a white organic electroluminescent device can be formed by simultaneously containing at least one organic compound layer that emits blue, green, or red light in addition to the organic light emitting compound of Formula (1) in the organic compound layer, and the blue, green, But are not limited to, those described in Application Serial Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428.
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, 구 동의 안정화를 얻을 수 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as "surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. 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. In this way, stabilization of the spherical augmentation can be obtained.
상기 칼코제나이드로서는 예컨대 SiOx(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON 등을 바람직하게 들 수 있으며, 할로겐화 금속으로서는 예컨대 LiF, MgF2, CaF2, 불화 희토류 금속 등을 바람직하게 들 수 있으며, 금속 산화물로서는 예컨대 Cs2O, Li2O, MgO, SrO, BaO, CaO 등을 바람직하게 들 수 있다.Examples of the chalcogenide include SiOx (1?X ? 2), AlOx (1?X ? 1.5), SiON and SiAlON. Examples of the halogenated metal include LiF, MgF2 , CaF2 , Rare-earth metals and the like. Preferable examples of the metal oxides include Cs2 O, Li2 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.In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, since the electron transfer compound is reduced to the anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing 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.
또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 전계 발광 소자를 제작할 수 있다.Also, a white light emitting device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.
본 발명에 따른 유기 발광 화합물은 유기 발광 소자의 전자전달층에 포함되어 소자의 구동 전압을 낮춤으로서 발광효율 및 소비 전력을 현저히 감소시킬 수 있는 장점이 있다.The organic luminescent compound according to the present invention is included in the electron transport layer of the organic light emitting device to lower the driving voltage of the device, thereby remarkably reducing the luminous efficiency and power consumption.
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 luminescent compound according to the present invention, the method for producing the same, and the luminescent characteristics of the device will be described in order to facilitate a detailed understanding of the present invention, but the present invention is not limited thereto. And are not intended to limit the scope of the invention.
[제조예 1] 화합물46의 제조[Preparation Example 1] Preparation of Compound46
화합물compoundCC의 제조Manufacturing
화합물 A 20.0 g(183.2 mmol), 화합물 B 47.8 g(183.2 mmol), DMSO 150 mL를 혼합하고 180 ℃에서 가열한다. 12시간 후 상온으로 냉각하고 증류수를 넣는다. 생성된 고체를 감압 여과하고 EA/MeOH로 재결정하여 화합물C 26.0 g(74.24 mmol, 40.5 %)을 얻었다.20.0 g (183.2 mmol) of Compound A, 47.8 g (183.2 mmol) of Compound B and 150 mL of DMSO are mixed and heated at 180 占 폚. After 12 hours, cool to room temperature and add distilled water. The resulting solid was filtered under reduced pressure and recrystallized with EA / MeOH to obtain 26.0 g (74.24 mmol, 40.5%) of CompoundC.
화합물compoundDD의 제조Manufacturing
화합물C 26.0 g(74.2 mmol)을 THF 300 mL에 녹이고, -78 ℃에서n-BuLi 35.6 mL(89.1 mmol, 2.5 M in Hexane)을 천천히 넣는다. 1시간 교반 후 trimethylborate 12.4 mL(111.4 mmol)를 넣는다. 10시간 교반 후 증류수를 넣고 EA로 추출한다. 감압 증류 후 MC/Hex으로 재결정하여 화합물D 14.0 g(44.4 mmol, 60.0%)를 얻었다.Dissolve 26.0 g (74.2 mmol) of CompoundC in 300 mL of THF and slowly add 35.6 mL (89.1 mmol, 2.5 M in Hexane) ofn- BuLi at -78 ° C. After stirring for 1 hour, add 12.4 mL (111.4 mmol) of trimethylborate. After stirring for 10 hours, add distilled water and extract with EA. After distillation under reduced pressure, the residue was recrystallized from MC / Hex to obtain 14.0 g (44.4 mmol, 60.0%) of CompoundD.
화합물compoundFF의 제조Manufacturing
화합물E 20.0 g(108.5 mmol)을 THF 1000 mL에 녹이고, 상온에서 phenylmagnesium bromide 83.1 mL(249.4 mmol, 3 M in diethyl ether)을 천천히 넣는다. 4시간 교반 후 증류수를 넣고 생성된 고체를 감압 여과하고, 고체를 EA로 재결정하여 화합물F18.0 g(67.2 mmol, 62.3%)을 얻었다.Dissolve 20.0 g (108.5 mmol) of compoundE in 1000 mL of THF and slowly add 83.1 mL (249.4 mmol, 3 M in diethyl ether) of phenylmagnesium bromide at room temperature. After stirring for 4 hours, distilled water was added, the resulting solid was filtered under reduced pressure, and the solid was recrystallized from EA to obtain 18.0 g (67.2 mmol, 62.3%) of CompoundF.
화합물compound4646의 제조Manufacturing
화합물F 10.0 g(137.4 mmol), 화합물D 12.9 g(41.1 mmol), Pd(PPh3)4 1.7 g(1.5 mmol), K2CO3 15.5 g(112.1 mmol), 증류수 55 mL, toluene 200 mL를 혼합하여 환류 교반한다. 8시간 후 상온으로 냉각하고 증류수를 넣는다. MC로 추출하고 황산마그네슘으로 건조한 후 감압 증류한다. 컬럼 분리 하여 화합물46 11.0 g(22.0 mmol, 59.2 %)을 얻었다.CompoundF 10.0 g (137.4 mmol), compoundD 12.9 g (41.1 mmol), Pd (PPh 3) 4 1.7 g (1.5 mmol), K 2 CO 3 15.5 g of (112.1 mmol), distilled water 55 mL, toluene 200 mL Mixed and refluxed and stirred. After 8 hours, cool to room temperature and add distilled water. Extracted with MC, dried with magnesium sulfate, and distilled under reduced pressure. The residue was subjected to column separation to obtain 11.0 g (22.0 mmol, 59.2%) of Compound46 .
[제조예 2] 화합물63의 제조[Preparation Example 2] Preparation of Compound63
화합물compoundAA의 제조Manufacturing
1,3-dibromobenzene 25.0 g(106.0 mmol), 2-naphthalene boronic acid 18.2 g(106.0 mmol), Pd(PPh3)4 4.8 g(4.2 mmol), Na2CO3 33.7 g(317.9 mmol), 증류수 150 mL, toluene 300 mL를 혼합하여 환류 교반한다. 12시간 후 상온으로 냉각하고 증류수를 넣는다. EA로 추출하고 황산마그네슘으로 건조한다. 감압 증류 후 컬럼 분리하여 화합물A 15.0 g(53.0 mmol, 50.5%)을 얻었다.1,3-dibromobenzene 25.0 g (106.0 mmol ), 2-naphthalene boronic acid 18.2 g (106.0 mmol), Pd (PPh 3) 4 4.8 g (4.2 mmol), Na 2 CO 3 33.7 g (317.9 mmol), distilled water 150 mL, and 300 mL of toluene are mixed and stirred under reflux. After 12 hours, cool to room temperature and add distilled water. Extract with EA and dry with magnesium sulfate. The mixture was distilled under reduced pressure and then subjected to column separation to obtain CompoundA (15.0 g, 53.0 mmol, 50.5%).
화합물compound B B의 제조Manufacturing
화합물A 15.0 g(53.0 mmol)을 THF 200 mL에 녹이고, -78 ℃에서n-BuLi 21 mL(53.0 mmol, 2.5 M in Hexane)을 천천히 넣는다. 1시간 후 1,3,5-trichloro-2,4,6-triazine 4.8 g(26.5 mmol)을 THF 100 mL에 녹인 용액에 -78 ℃에서 넣는다. 5시간 교반 후 증류수를 넣고 EA로 추출하였다. 황산마그네슘으로 건조하고 감압 증류한 후, 컬럼 분리하여 화합물B 8.0 g(15.4 mmol, 59.2%)을 얻었다.Dissolve compoundA (15.0 g, 53.0 mmol) in 200 mL of THF and slowly add 21 mL (53.0 mmol, 2.5 M in Hexane) ofn- BuLi at -78 ° C. After 1 hour, add 4.8 g (26.5 mmol) of 1,3,5-trichloro-2,4,6-triazine in 100 mL of THF at -78 ° C. After stirring for 5 hours, distilled water was added and extracted with EA. Dried over magnesium sulfate, distilled under reduced pressure, and subjected to column separation to obtain 8.0 g (15.4 mmol, 59.2%) of CompoundB.
화합물compoundEE의 제조Manufacturing
화합물C 25.0 g(199.7 mmol), 화합물D 36.9 g(199.7 mmol), DMSO 200 mL를 혼합하여 180 ℃에서 가열한다. 12시간 후 상온으로 냉각하고 증류수를 넣는다. 생성된 고체를 감압 여과하고 EA/MeOH로 재결정하여 화합물E14.0 g(48.2 mmol, 24.2 %)을 얻었다.Compound (C ) (25.0 g, 199.7 mmol), Compound (D ) (36.9 g, 199.7 mmol) and DMSO (200 mL) were mixed and heated at 180 ° C. After 12 hours, cool to room temperature and add distilled water. The resulting solid was filtered under reduced pressure and recrystallized from EA / MeOH to obtain 14.0 g (48.2 mmol, 24.2%) of compoundE.
화합물compoundFF의 제조Manufacturing
화합물E 14.0 g(48.2 mmol)을 THF 200 mL에 녹이고, -78 ℃에서n-BuLi 19.2 mL(48.2 mmol, 2.5M in Hexane)을 천천히 넣는다. 1시간 교반 후 trimethylborate 6.9 mL(62.7 mmol)을 넣는다. 10시간 교반 후 증류수를 넣고 EA로 추출한다. 감압 증류 후 컬럼 분리하여 화합물 F 8.0 g(31.4 mmol, 65.3%)를 얻었다.Dissolve 14.0 g (48.2 mmol) of compoundE in 200 mL of THF and slowly addn- BuLi 19.2 mL (48.2 mmol, 2.5 M in Hexane) at -78 ° C. After stirring for 1 hour, add 6.9 mL (62.7 mmol) of trimethylborate. After stirring for 10 hours, add distilled water and extract with EA. After distillation under reduced pressure, column separation was conducted to obtain 8.0 g (31.4 mmol, 65.3%) of CompoundF.
화합물compound 63 63의 제조Manufacturing
화합물B 4.0 g(7.7 mmol), 화합물F 2.4 g(9.2 mmol), Pd(PPh3)4 0.4 g(0.3 mmol), Na2CO3 2.4 g(23.1 mmol) 증류수 10 mL, toluene 50 mL을 혼합하여 환류 교반한다. 8시간 후 상온으로 냉각하고 증류수를 넣는다. MC로 추출하고 황산마그네슘으로 건조한 후 감압 증류한다. 컬럼 분리 하여 화합물633.4 g(4.9 mmol, 63.6%) 을 얻었다.CompoundB 4.0 g (7.7 mmol), CompoundF 2.4 g (9.2 mmol), Pd (PPh 3) 4 0.4 g (0.3 mmol), Na 2 CO 3 2.4 g (23.1 mmol) of distilled water 10 mL, toluene mixed with 50 mL Followed by reflux stirring. After 8 hours, cool to room temperature and add distilled water. Extracted with MC, dried with magnesium sulfate, and distilled under reduced pressure. The mixture was subjected to column separation to obtain 3.4 g (4.9 mmol, 63.6%) of Compound63 .
[제조예 3] 화합물67의 제조[Preparation Example 3] Preparation of Compound67
화합물compoundCC의 제조Manufacturing
화합물A 30.0 g(162.8 mmol), 화합물B 30.1 g(162.8 mmol), DMSO 200 mL을 혼합하여 180 ℃에서 가열한다. 12시간 후 상온으로 냉각하고 증류수를 넣는다. 생성된 고체를 감압 여과하고 컬럼 분리하여 화합물C 11.0 g(31.5 mmol, 19.5%)을 얻었다.Is heated in the compoundA 30.0 g (162.8 mmol), CompoundB 30.1 g (162.8 mmol), 180 ℃ a mixture of 200 mL DMSO. After 12 hours, cool to room temperature and add distilled water. The resulting solid was filtered under reduced pressure and subjected to column separation to obtain 11.0 g (31.5 mmol, 19.5%) of CompoundC.
화합물compoundDD의 제조Manufacturing
화합물C 11.0 g(31.5 mmol)을 THF 100mL에 녹이고, -78 ℃에서n-BuLi 12.5 mL(31.5 mmol, 2.5 M in Hexane)을 천천히 넣는다. 1시간 교반 후 trimethylborate 5.2 mL(47.2 mmol)을 넣는다. 10시간 교반 후 증류수를 넣고 EA로 추출한다. 감압 증류 후 컬럼 분리하여 화합물D 5.0 g(15.9 mmol, 51.3%)를 얻었다.Dissolve 11.0 g (31.5 mmol) of compoundC in 100 mL of THF and slowly add 12.5 mL (31.5 mmol, 2.5 M in Hexane) ofn- BuLi at -78 ° C. After stirring for 1 hour, add 5.2 mL (47.2 mmol) of trimethylborate. After stirring for 10 hours, add distilled water and extract with EA. After distillation under reduced pressure, column separation was conducted to obtain 5.0 g of compoundD (15.9 mmol, 51.3%).
화합물compoundFF의 제조Manufacturing
4-Chloropyridine 22.6 mL(238.6 mmol)을 MC 100 mL에 녹이고 -15 ℃에서n- BuLi 95 mL(238.6 mmol, 2.5 M in Hexane)을 천천히 넣는다. 1시간 후 1,3,5-trichloro-2,4,6-triazine 20.0 g(108.5 mmol)을 MC 100 mL에 녹인 용액에 -15 ℃에서 넣는다. 5시간 교반 후 증류수를 넣고 EA로 추출하였다. 황산마그네슘으로 건조하고 감압 증류한 후 컬럼 분리하여 화합물F 11.0 g(40.8 mmol, 37.6%)을 얻었다.Dissolve 22.6 mL (238.6 mmol) of 4-chloropyridine in 100 mL of MC and slowly add 95 mL (238.6 mmol, 2.5 M in Hexane) ofn -BuLi at -15 ° C. After 1 hour, add 20.0 g (108.5 mmol) of 1,3,5-trichloro-2,4,6-triazine in 100 mL of MC at -15 ° C. After stirring for 5 hours, distilled water was added and extracted with EA. Dried over magnesium sulfate, distilled under reduced pressure, and subjected to column separation to obtain 11.0 g (40.8 mmol, 37.6%) of Compound (F ).
화합물compound6767의 제조Manufacturing
화합물D 5.0 g(15.9 mmol), 화합물F 4.3 g(15.9 mmol), Pd(PPh3)4 0.7 g(0.6 mmol), Na2CO3 5.1 g(47.7 mmol) 증류수 20 mL, toluene 100 mL 을 혼합하여 환류 교반한다. 8시간 후 상온으로 냉각하고 증류수를 넣는다. MC로 추출하고 황산마그네슘으로 건조하고 감압 증류한 후, 컬럼 분리 하여 화합물67 3.8 g(7.5 mmol, 50.3%)을 얻었다.CompoundD 5.0 g (15.9 mmol), CompoundF 4.3 g (15.9 mmol), Pd (PPh 3) 4 0.7 g (0.6 mmol), Na 2 CO 3 5.1 g (47.7 mmol) of distilled water 20 mL, toluene mixture to 100 mL Followed by reflux stirring. After 8 hours, cool to room temperature and add distilled water. Extracted with MC, dried over magnesium sulfate, distilled under reduced pressure, and then subjected to column separation to obtain 3.8 g (7.5 mmol, 50.3%) of compound67 .
상기 제조예 1 내지 제조예 3의 방법을 이용하여 유기 발광 화합물1 내지 화합물72를 제조하였으며, 표 1에 제조된 유기 발광 화합물들의1H NMR 및 MS/FAB를 나타내었다.Organic luminescent compounds1 to72 were prepared using the methods of Preparation Examples 1 to 3, and1 H NMR and MS / FAB of the organic luminescent compounds prepared in Table 1 were shown.
[표 1][Table 1]
[실시예 1] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작[Example 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 fabricated.
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 a glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water sequentially and then stored in isopropanol Respectively.
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)triphenylNext, an ITO substrate was placed on a substrate folder of a vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl
amine(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.(2-TNATA) was added and the chamber was evacuated until the degree of vacuum reached 10 -6 torr. Then, a current was applied to the cell to evaporate the 2-TNATA to form a 60 nm thick hole injection layer on the ITO substrate Respectively.
이어서, 진공 증착 장비 내의 다른 셀에 하기구조N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.The NPB -diphenyl-4,4'-diamine into the (NPB), by applying a current to the cell - Then, to another cell of the vacuum vapor-deposit device structure,N, N 'N, N -bis (α-naphthyl)' And evaporated to deposit a hole transport layer having a thickness of 20 nm on the hole injection layer.
정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 발광 재료로 호스트 재료인 dinaphthylanthracene(DNA)을 넣고, 또 다른 셀에는 하기 구조를 가진 화합물 D를 넣은 후, 두 셀을 같이 가열, 화합물 D의 증착속도 비율을 2 내지 5 중량%로 증착함으로써 상기 정공 전달층 위에 30 nm 두께의 발광층을 증착하였다.A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. The host material Dinaphthylanthracene (DNA) was added as a light emitting material to one cell in the vacuum vapor deposition equipment, and the other cell was loaded with the compound D having the following structure. Then, the two cells were heated together, and the deposition rate ratio of the compound D was 2 to 5 By weight of a hole transporting layer to deposit a light emitting layer with a thickness of 30 nm on the hole transporting layer.
이어서 전자전달층으로써 본 발명에 따른 화합물3을 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, compound3 according to the present invention was deposited to a thickness of 20 nm as an electron transfer layer, and lithium quinolate (Liq) having the following structure was deposited as an electron injecting layer to a thickness of 1 to 2 nm and then using another vacuum deposition equipment An Al cathode was deposited to a thickness of 150 nm to fabricate an OLED.
재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 OLED 발광재료로 사용하였다.Each compound was purified by vacuum sublimation at 10-6 torr and used as an OLED light emitting material.
[비교예 1]종래의 발광 재료를 이용한 OLED 소자의 발광 특성[Comparative Example 1] Luminescence characteristics of OLED device using conventional light emitting material
실시예 1과 정공주입층, 정공전달층, 발광층을 형성시킨 후, 전자전달층으로써 하기 구조의 Alq(tris(8-hydroxyquinoline)-aluminum(III))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 OLED를 제작하였다.Alq (tris (8-hydroxyquinoline) -aluminum (III)) having the following structure was vapor-deposited as an electron transfer layer to a thickness of 20 nm after forming the hole injecting layer, hole transporting layer and light emitting layer in Example 1, Lithium quinolate (Liq) as a layer was deposited to a thickness of 1 to 2 nm, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition apparatus to fabricate an OLED.
상기 실시예 1 및 비교예 1에서 제조된 본 발명에 따른 유기발광화합물과 종 래의 발광 화합물을 함유하는 OLED 소자의 발광 효율을 각각 1,000 cd/m2에서 측정하여 하기 표 2에 나타내었다.The luminous efficiencies of the organic light emitting compounds according to the present invention prepared in Example 1 and Comparative Example 1 and OLED devices containing the following light emitting compounds were measured at 1,000 cd / m2 , respectively, and are shown in Table 2 below.
[표 2][Table 2]
본 발명에서 개발한 화합물들이 성능 측면에서 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다.It was confirmed that the compounds developed in the present invention show superior properties in terms of performance compared to conventional materials.
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Also Published As
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| WO2010126270A1 (en) | 2010-11-04 |
| KR20100118690A (en) | 2010-11-08 |
| TW201100522A (en) | 2011-01-01 |
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