KR20100106014A - 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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- KR20100106014A KR20100106014A KR1020090024431A KR20090024431A KR20100106014A KR 20100106014 A KR20100106014 A KR 20100106014A KR 1020090024431 A KR1020090024431 A KR 1020090024431A KR 20090024431 A KR20090024431 A KR 20090024431A KR 20100106014 A KR20100106014 A KR 20100106014A
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- Prior art keywords
- substituted
- unsubstituted
- organic
- light emitting
- ring
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- 150000007517 lewis acids Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Abstract
Description
본 발명은 신규한 유기 발광 화합물, 이를 포함하고 있는 유기 전계 발광 소자에 관한 것으로서, 더욱 상세하게는 본 발명에 따른 유기 발광 화합물은 유기 전계 발광 소자의 정공전달층 또는 정공주입층에 포함될 수 있다.The present invention relates to a novel organic light emitting compound, and an organic electroluminescent device comprising the same, and more particularly, the organic light emitting compound according to the present invention may be included in the hole transport layer or the hole injection layer of the organic electroluminescent 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 element that has a wide viewing angle, excellent contrast, and high response speed.Eastman Kodak Co., Ltd. in 1987 An organic EL device using a low molecular aromatic diamine and an aluminum complex as a light emitting layer formation material was first developed [Appl. Phys. Lett. 51, 913, 1987].
유기 EL 소자는 전자 주입 전극(음극) 과 정공 주입 전극(양극) 사이에 형성된 유기막에 전하를 주입하면 전자와 정공이 쌍을 이룬 후 소멸하면서 빛을 내는 소자이다. 플라스틱 같은 휠 수 있는(flexible) 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널(Plasma Display Panel)이나 무기 EL 디스플레이에 비해 낮은 전압에서 (10V이하) 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있다. An organic EL device is a device that emits light when an electron is injected into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) and then disappears after pairing electrons and holes. The device can be formed on a flexible transparent substrate such as plastic, and can be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic EL display, and has a relatively low power consumption. It has a small and excellent color.
유기 EL 소자에서 유기재료는 크게 발광재료와 전하수송재료로 나눌 수 있다. 발광재료는 발광색 및 발광효율에 직접적으로 관계가 있는데, 요구되는 몇 가지 특성으로는 고체상태에서 형광 양자 수율이 커야하고, 전자와 정공의 이동도가 높아야 하며, 진공 증착시 쉽게 분해되지 않아야 하고, 균일한 박막을 형성, 안정해야한다. Organic materials in organic EL devices can be roughly divided into light emitting materials and charge transport materials. The luminescent material is directly related to the emission color and the luminous efficiency. Some of the required properties are that the fluorescence quantum yield should be high in the solid state, the mobility of electrons and holes should be high, and not easily decomposed during vacuum deposition. It should be stable, forming a uniform thin film.
한편, 정공 주입 및 수송 재료로는 구리 프탈로시아닌(CuPc), 4,4'-비스[N-(1-나프틸)-N-페닐아미노]바이페닐(4,4'-bis[N-(1-naphthyl)-N-phenylamino]-biphe nyl; NPB), N,N'-다이페닐-N,N'-비스(3-메틸페닐)-(1,1'-바이페닐)-4,4'-다이아민(N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'biphenyl)-4,4'-diamine; TPD), MTDATA(4, 4', 4"-tris(3-methylphenylphenylamino)triphenylamine) 등이 있다. 이러한 물질을 정공 주입 및 수송층에 포함시킨 소자는 효율 및 수명이 저하되는 문제가 있었다. 그 이유는 유기 EL 소자를 높은 전류에서 구동하게 되면, 양극과 정공 주입층 사이에서 열 스트레스(Thermal stress)가 발생하고, 이러한 열 스트레스에 의해 소자의 수명이 급격히 저하되기 때문이다. 또한, 정공 주입층에 사용되는 유기물질은 정공의 운동성이 매우 크기 때문에, 정공과 전자의 전하 밸런스(hole-electron charge balance)가 깨지고 이로 인해 양자 효율(cd/A)이 낮아지게 된다. Meanwhile, as the hole injection and transport material, copper phthalocyanine (CuPc), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (4,4'-bis [N- (1 -naphthyl) -N-phenylamino] -biphe nyl; NPB), N, N'-diphenyl-N, N'-bis (3-methylphenyl)-(1,1'-biphenyl) -4,4'- Diamine (N, N'-diphenyl-N, N'-bis (3-methylphenyl)-(1,1'biphenyl) -4,4'-diamine; TPD), MTDATA (4, 4 ', 4 "- tris (3-methylphenylphenylamino) triphenylamine), etc. A device incorporating such a material into the hole injection and transport layer has a problem of deterioration in efficiency and lifetime, because when the organic EL device is driven at high current, This is because thermal stress is generated between the hole injection layers, and the lifespan of the device is drastically reduced due to such heat stress.In addition, since the organic material used in the hole injection layer has very high hole mobility, The hole-electron charge balance is not broken This lowers the quantum efficiency (cd / A).
유기 EL소자의 내구성을 높이기 위해서는 박막 안정성이 양호한 화합물과 비결정성이 높은 화합물일수록 박막 안정성이 높다고 보고되어 있다. 이때 비결정성의 지표로서 유리전이점(Tg)이 사용된다.In order to increase the durability of the organic EL device, it is reported that the compound having good thin film stability and the compound having high amorphousness have higher thin film stability. At this time, the glass transition point (Tg) is used as an index of amorphousness.
기존의 MTDATA의 유리전이온도는 76℃로서 비결정성이 높다고는 할 수 없다. 이러한 재료들은 유기 EL 소자의 내구성면에서, 또한 정공주입, 수송의 특성에 기인하는 발광효율에서도 만족스러운 특성을 얻지 못하였다.MTDATA's glass transition temperature is 76 ℃, which means that its amorphousness is not high. These materials did not obtain satisfactory characteristics in terms of durability of the organic EL element and also in luminous efficiency due to the characteristics of hole injection and transport.
따라서 본 발명의 목적은 상기한 문제점들을 해결하기 위하여 기존의 정공주입 또는 정공전달 재료보다 발광 효율 및 소자 수명이 좋은 우수한 골격의 유기 발광 화합물을 제공하는 것이며, 신규한 유기 발광 화합물을 정공주입층 또는 정공전달층에 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 luminescence efficiency and device life better than the existing hole injection or hole transport material in order to solve the above problems, and to provide a novel organic light emitting compound in the hole injection layer or An organic electroluminescent element employed in a hole transport layer is provided.
본 발명은 하기 화학식 1로 표시되는 유기 발광 화합물, 이를 포함하고 있는 유기 전계 발광 소자에 관한 것으로, 본 발명에 따른 유기 발광 화합물은 유기 전계 발광 소자의 정공주입층 또는 정공전달층에 포함되어 소자의 구동전압을 낮추면서 발광효율을 개선시킬 수 있다.The present invention relates to an organic light emitting compound represented by Chemical Formula 1, and an organic electroluminescent device comprising the same, wherein the organic light emitting compound according to the present invention is included in the hole injection layer or the hole transport layer of the organic electroluminescent device The luminous efficiency can be improved while lowering the driving voltage.
[화학식 1][Formula 1]
[상기 화학식 1에서, [In Formula 1,
A 고리 및 B 고리는 서로 독립적으로 단일환 또는 다환의 방향족 고리, 단일환 또는 다환의 헤테로 방향족 고리, 방향족 고리가 융합된 5원 내지 6원의 헤테로 방향족 고리 또는 5원 내지 6원의 헤테로 방향족 고리가 융합된 단일환 또는 다환 의 방향족 고리이고, 단 A 고리와 B 고리가 동시에 단일환의 방향족 고리인 경우 치환기인 R4 및 R5가 서로 독립적으로 수소, (C1-C60)알킬, (C1-C60)알콕시 또는 (C6-C60)아릴은 제외하며; A ring and B ring are each independently a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- to 6-membered heteroaromatic ring in which the aromatic ring is fused or a 5- to 6-membered heteroaromatic ring Are a fused monocyclic or polycyclic aromatic ring, provided that A 4 and R 5 are simultaneously monocyclic aromatic rings, and substituents R 4 and R 5 are independently of each other hydrogen, (C1-C60) alkyl, (C1- C60) alkoxy or (C6-C60) aryl is excluded;
L1은 치환 또는 비치환된(C6-C60)아릴렌, 치환 또는 비치환된(C3-C60)헤테로아릴렌, 치환 또는 비치환된(C3-C60)알케닐렌 또는 치환 또는 비치환된(C3-C60)알키닐렌이고;L 1 is substituted or unsubstituted (C6-C60) arylene, substituted or unsubstituted (C3-C60) heteroarylene, substituted or unsubstituted (C3-C60) alkenylene or substituted or unsubstituted (C3 -C60) alkynylene;
Ar1은 치환 또는 비치환된 (C1-C60)알킬, 치환 또는 비치환된(C6-C60)아릴, 치환 또는 비치환된(C3-C60)헤테로아릴, 치환 또는 비치환된 헤테로시클로알킬, 치환 또는 비치환된 (C3-C60)시클로알킬, 치환 또는 비치환된 아다만틸, 치환 또는 비치환된(C7-C60)바이시클로알킬, 치환 또는 비치환된(C3-C60)의 알케닐 또는 치환 또는 비치환된(C3-C60)알키닐이고;Ar 1 is substituted or unsubstituted (C1-C60) alkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (C3-C60) heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted Or unsubstituted (C3-C60) cycloalkyl, substituted or unsubstituted adamantyl, substituted or unsubstituted (C7-C60) bicycloalkyl, substituted or unsubstituted (C3-C60) alkenyl or substituted Or unsubstituted (C3-C60) alkynyl;
R1, R2, R3, R4 , R5 , R6 및 R7는 서로 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된(C1-C60)알킬, 치환 또는 비치환된(C6-C60)아릴, 치환 또는 비치환된(C3-C60)헤테로아릴, N, O 및 S로부터 선택된 하나 이상을 포함하는 5원 내지 6원의 치환 또는 비치환된 헤테로시클로알킬, 치환 또는 비치환된(C3-C60)시클로알킬, 치환 또는 비치환된 트리(C1-C60)알킬실릴, 치환 또는 비치환된 디(C1-C60)알킬(C6-C60)아릴실릴, 치환 또는 비치환된 트리(C6-C60)아릴실릴, 치환 또는 비치환된 아다만틸, 치환 또는 비치환된(C7-C60)바이시클로알킬, 시아노, 치환 또는 비치환된(C1-C60)알킬옥시, 치환 또는 비치환된(C1-C60)알킬티오, 치환 또는 비치환 된(C6-C60)아릴옥시, 치환 또는 비치환된(C6-C60)아릴티오, 치환 또는 비치환된(C1-C60)알콕시카보닐, 치환 또는 비치환된(C1-C60)알킬카보닐, 치환 또는 비치환된(C6-C60)아릴카보닐, 치환 또는 비치환된(C6-C60)아릴옥시카보닐, 치환 또는 비치환된(C1-C60)알콕시카보닐옥시, 치환 또는 비치환된(C1-C60)알킬카보닐옥시, 치환 또는 비치환된(C6-C60)아릴카보닐옥시, 치환 또는 비치환된(C6-C60)아릴옥시카보닐옥시, 카르복실, 나이트로 또는 하이드록시이거나, 서로 인접한 치환기들이 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 융합고리를 형성할 수 있고;R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C60) alkyl, substituted or unsubstituted (C6- C60) aryl, substituted or unsubstituted (C3-C60) heteroaryl, 5- to 6-membered substituted or unsubstituted heterocycloalkyl containing one or more selected from N, O and S, substituted or unsubstituted ( C3-C60) cycloalkyl, substituted or unsubstituted tri (C1-C60) alkylsilyl, substituted or unsubstituted di (C1-C60) alkyl (C6-C60) arylsilyl, substituted or unsubstituted tri (C6- C60) arylsilyl, substituted or unsubstituted adamantyl, substituted or unsubstituted (C7-C60) bicycloalkyl, cyano, substituted or unsubstituted (C1-C60) alkyloxy, substituted or unsubstituted ( C1-C60) alkylthio, substituted or unsubstituted (C6-C60) aryloxy, substituted or unsubstituted (C6-C60) arylthio, substituted or unsubstituted (C1-C60) alkoxycarbonyl, substituted or unsubstituted Cyclic (C1-C60) alkylcarbonyl, Substituted or unsubstituted (C6-C60) arylcarbonyl, substituted or unsubstituted (C6-C60) aryloxycarbonyl, substituted or unsubstituted (C1-C60) alkoxycarbonyloxy, substituted or unsubstituted ( C1-C60) alkylcarbonyloxy, substituted or unsubstituted (C6-C60) arylcarbonyloxy, substituted or unsubstituted (C6-C60) aryloxycarbonyloxy, carboxyl, nitro or hydroxy, or Substituents adjacent to each other may be linked to (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form a fused ring;
상기 L1, Ar1, R1 내지 R7에 치환 또는 비치환되는 치환기는 수소, 중수소, 할로겐, (C1-C60)알킬, (C6-C60)아릴, (C3-C60)헤테로아릴, (C3-C60)시클로알킬, 시아노, (C1-C60)알킬옥시, (C1-C60)알킬티오, (C6-C60)아릴옥시, (C6-C60)아릴티오, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴, 트리(C6-C60)아릴실릴, NR31R32, PR33R34, BR35R36, P(=O)R37R38로 이루어진 군으로부터 선택되는 하나 이상의 치환기이거나 인접한 치환들이 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며;The substituent substituted or unsubstituted in L 1 , Ar 1 , R 1 to R 7 is hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C3-C60) heteroaryl, (C3 -C60) cycloalkyl, cyano, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, tri (C1-C60) alkylsilyl, Consisting of di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, NR 31 R 32 , PR 33 R 34 , BR 35 R 36 , P (= O) R 37 R 38 One or more substituents selected from the group or adjacent substitutions may be linked to (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form a fused ring;
R31 내지 R38은 서로 독립적으로 (C1-C60)알킬, (C3-C60)시클로알킬, (C6-C60)아릴 또는 (C3-C60)헤테로아릴이거나, 서로 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C60)알킬렌 또는 (C3-C60)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 R31 내지 R38의 알킬, 시클로알킬, 아릴 및 헤테로아릴은 수 소, 중수소, 할로겐, (C1-C60)알킬, 할로(C1-C60)알킬, (C6-C60)아릴, (C6-C60)아릴이 치환되거나 치환되지 않은 (C3-C60)헤테로아릴, 시아노, 카르복실, 나이트로 또는 하이드록시로 이루어진 군으로부터 선택되는 하나 이상의 치환기가 더 치환될 수 있다.]R 31 to R 38 independently of one another are (C 1 -C 60) alkyl, (C 3 -C 60) cycloalkyl, (C 6 -C 60) aryl or (C 3 -C 60) heteroaryl, or include or comprise a fused ring with adjacent substituents Unsubstituted (C3-C60) alkylene or (C3-C60) alkenylene to form a fused ring, wherein alkyl, cycloalkyl, aryl and heteroaryl of R 31 to R 38 are hydrogen, deuterium, Halogen, (C1-C60) alkyl, halo (C1-C60) alkyl, (C6-C60) aryl, (C6-C60) aryl with or without (C3-C60) heteroaryl, cyano, carboxyl, One or more substituents selected from the group consisting of nitro or hydroxy may be further substituted.]
본 발명에 기재된 「알킬」은 탄소 원자 및 수소 원자만으로 구성된 직쇄 또는 분지쇄의 포화된 1가 탄화수소 라디칼 또는 그의 조합물을 포함하며, 또한, 「알킬옥시」 또는 「알킬티오」는 각각 -O-알킬기 또는 -S-알킬기로, 여기서 알킬은 상기 정의한 바와 같다."Alkyl" described in the present invention includes a straight or branched chain saturated monovalent hydrocarbon radical or a combination thereof composed of only carbon and hydrogen atoms, and "alkyloxy" or "alkylthio" are each -O-. Alkyl group or -S-alkyl group, wherein alkyl is as defined above.
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 포함한다. 또한, 하나이상의 아릴이 화학결합을 통하여 결합되어 있는 구조도 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트라이페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 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 is a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes the system. Also included are structures in which one or more aryls are bonded via a chemical bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like. It is not limited to this.
본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 질소(N), 산소(O), 황(S), 인(P) 또는 규소(Si)로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠 환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 하나 이상의 헤테로아릴이 화학결합을 통 하여 결합되어 있는 구조도 포함된다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페난트리딘일, 벤조디옥솔릴 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다.The "heteroaryl" described in the present invention includes 1 to 4 heteroatoms selected from nitrogen (N), oxygen (O), sulfur (S), phosphorus (P) or silicon (Si) as aromatic ring skeleton atoms. , An aryl group in which the remaining aromatic ring skeleton atoms are carbon, 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. Also included are structures in which one or more heteroaryls are bonded via chemical bonds. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetra Monocyclic heteroaryl such as zolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothia Zolyl, Benzoisoxazolyl, Benzoxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cinolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Phenantridinyl , Polycyclic heteroaryls such as benzodioxolyl and the like, and their corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like. .
또한, 본 발명에 기재되어 있는 “(C1-C60)알킬”부분이 포함되어 있는 치환체들은 1 내지 60개의 탄소수를 가질 수도 있고, 1 내지 20개의 탄소수를 가질 수도 있고, 1 내지 10개의 탄소수를 가질 수도 있다. “(C6-C60)아릴”부분이 포함되어 있는 치환체들은 6 내지 60개의 탄소수를 가질 수도 있고, 6 내지 20개의 탄소수를 가질 수도 있고, 6 내지 12개의 탄소수를 가질 수도 있다. “(C3-C60)헤테로아릴”부분이 포함되어 있는 치환체들은 3 내지 60개의 탄소수를 가질 수도 있고, 4 내지 20개의 탄소수를 가질 수도 있고, 4 내지 12개의 탄소수를 가질 수도 있다. “(C3-C60)시클로알킬”부분이 포함되어 있는 치환체들은 3 내지 60개의 탄소수를 가질 수도 있고, 3 내지 20개의 탄소수를 가질 수도 있고, 3 내지 7개의 탄소수를 가질 수도 있다. “(C2-C60)알케닐 또는 알키닐”부분이 포함되어 있는 치환체들은 2 내지 60개의 탄소수를 가질 수도 있고, 2 내지 20개의 탄소수를 가질 수도 있고, 2 내지 10개의 탄소수를 가질 수도 있다. In addition, substituents containing the “(C 1 -C 60) alkyl” moiety described in the present invention may have 1 to 60 carbon atoms, 1 to 20 carbon atoms, or 1 to 10 carbon atoms. It may be. Substituents containing the "(C6-C60) aryl" moiety may have 6 to 60 carbon atoms, 6 to 20 carbon atoms, or 6 to 12 carbon atoms. Substituents containing the "(C3-C60) heteroaryl" moiety may have 3 to 60 carbon atoms, 4 to 20 carbon atoms, or 4 to 12 carbon atoms. Substituents containing the "(C3-C60) cycloalkyl" moiety may have 3 to 60 carbon atoms, may have 3 to 20 carbon atoms, or may have 3 to 7 carbon atoms. Substituents containing the "(C2-C60) alkenyl or alkynyl" moiety may have 2 to 60 carbon atoms, may have 2 to 20 carbon atoms, or may have 2 to 10 carbon atoms.
본 발명의 유기 발광 화합물은 하기 화학식 2 내지 5로 표시되는 화합물을 포함한다.The organic light emitting compound of the present invention includes a compound represented by the following formula (2) -5.
[화학식 2][Formula 2]
[화학식 3](3)
[화학식 4][Formula 4]
[화학식 5][Chemical Formula 5]
[상기 화학식 2 내지 5에서, A고리, B고리, L1, Ar1, 및 R1 내지 R7는 상기 화학식 1에서의 정의와 동일하다.][In Formula 2 to 5, Ring A, Ring B, L 1 , Ar 1 , and R 1 to R 7 are the same as defined in Formula 1 above.]
상기 A고리 및 B고리는 서로 독립적으로 벤젠, 나프탈렌, 안트라센, 피리딘, 퀴놀린, 이소퀴놀린 또는 퀴녹살린이나 이에 한정되지 않으며, A고리와 B고리가 동시에 벤젠인 경우 A고리와 B고리에 치환되는 R4 및 R5가 서로 독립적으로 수소, (C1-C60)알킬, (C1-C60)알콕시 또는 (C6-C60)아릴은 제외된다.Ring A and ring B are independently from each other benzene, naphthalene, anthracene, pyridine, quinoline, isoquinoline or quinoxaline or not limited thereto, and when ring A and ring B are benzene, R is substituted with ring A and ring B at the same time. 4 and R 5 independently of each other exclude hydrogen, (C1-C60) alkyl, (C1-C60) alkoxy or (C6-C60) aryl.
더욱 구체적으로, 상기 
[상기 R3, R4 및 R5는 상기 화학식 1에서의 정의와 동일하다.][R 3 , R 4 and R 5 are the same as defined in the formula (1).]
보다 바람직하게, 상기 
[R3 및 R51은 서로 독립적으로 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, 벤질, 페닐, 나프틸, 비페닐, 플루오레닐, 스피로바이플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 퀴놀릴, 이소퀴놀릴 또는 트리아지닐이고, 상기 페닐, 나프틸, 비페닐, 플루오레닐, 스피로바이플루오레닐, 페난트릴, 안트릴, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 퀴놀릴, 이소퀴놀릴 또는 트리아지닐은 중수소, 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, 페닐, 나프틸 또는 피리딜로 더 치환될 수 있다.][R 3 and R 51 independently of one another are 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, benzyl, phenyl, naphthyl, biphenyl, fluorenyl, spirobifluorenyl, phenanthryl, anthryl, fluoranthenyl , Triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, quinolyl, isoquinolyl or triazinyl, the phenyl, naphthyl, biphenyl, fluorenyl, spirobifluorenyl, Phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, quinolyl, isoquinolyl or triazinyl are deuterium, 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, phenyl, naphthyl Or may be further substituted with pyridyl C]
본 발명에 따른 유기 발광 화합물은 보다 구체적으로 하기의 화합물로서 예 시될 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.
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
[상기 반응식 1에서, Ar1, L1 및 R1 내지 R7는 상기 화학식 1에서의 정의와 동일하다.][In Reaction Scheme 1, Ar 1 , L 1 and R 1 to R 7 are the same as defined in the formula (1).]
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 정공주입층 또는 정공수송층의 재료로 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 material of a hole injection layer or a hole 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.In addition, the organic material layer is characterized in that it comprises at least one layer comprising the organic light emitting compound of Formula 1 and at least one layer consisting of a fluorescent host-fluorescent dopant or a phosphorescent host-phosphorescent dopant, the organic electroluminescence of the present invention The fluorescent host, fluorescent dopant, phosphorescent host or phosphorescent dopant applied to the device is not particularly limited.
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 착체 화합물을 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 compounds 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 적색, 녹색 및 청색 발광을 하는 유기발광층을 하나 이상을 동시에 포함하여 백색 발광을 하는 백색발광소자를 형성할 수 있다. 상기 청색, 녹색 또는 적색 발광을 하는 화합물은 출원번호 제10-2008-0123276호, 제10-2008-0107606호 또는 제10-2008-0118428호에 예시되어 있으나, 이에 한정되지는 않는다. In addition, a white light emitting device that emits white light may be formed on the organic material layer by simultaneously including one or more organic light emitting layers emitting red, green, and blue light in addition to the organic light emitting compound. The compound emitting blue, green, or red light is exemplified in Application Nos. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.
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.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.
본 발명에 따른 유기 발광 화합물은 유기 전계 발광 소자의 정공주입층 또는 정공전달층에 포함되어 소자의 구동전압을 낮추면서 발광효율을 개선시킬 수 있다. 특히 견고한 카바졸 유도체를 함유하여 삼중항 간격(triplet gap)이 큰 유기물을 구성하게 된다. 이는 인광소자에서 종래의 재료 보다 효율적으로 여기자를 저지하는(exciton blocking) 역할을 하여 발광효율을 높이고 장수명의 소자를 제공할 수 있다. The organic light emitting compound according to the present invention may be included in the hole injection layer or the hole transport layer of the organic EL device to improve the luminous efficiency while lowering the driving voltage of the device. In particular, it contains a strong carbazole derivative to form a large organic triplet gap (triplet gap). This may serve to block excitons more efficiently than conventional materials in phosphorescent devices, thereby improving luminous efficiency and providing long-life devices.
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 4의 제조Preparation Example 1 Preparation of Compound 4
화합물 compound AA 의 제조Manufacture
2-나프톨 20.0 g(138.8 mmol), NaHSO3 28.8 g(277.4 mmol), 증류수 160 mL, 4-브로모페닐하이드라진 31.2 mL(166.4 mmol)를 넣고 120℃로 가열시켰다. 12시간 후 증류수를 넣고 생성된 고체를 감압 여과하였다. 얻어진 고체를 염산 수용액에 넣고 100℃로 가열시켰다. 한시간 후 디클로로메탄으로 추출하고 증류수와 NaOH 수용액으로 씻어주었다. 컬럼 분리하여 화합물 A 9.2 g(31.0 mmol, 22.4 %)을 얻었다. 20.0 g (138.8 mmol) of 2-naphthol, 28.8 g (277.4 mmol) of NaHSO 3 , 160 mL of distilled water, and 31.2 mL (166.4 mmol) of 4-bromophenylhydrazine were added and heated to 120 ° C. After 12 hours, distilled water was added and the resulting solid was filtered under reduced pressure. The obtained solid was put into aqueous hydrochloric acid solution and heated to 100 degreeC. After an hour, the mixture was extracted with dichloromethane and washed with distilled water and aqueous NaOH solution. 9.2 g (31.0 mmol, 22.4%) of Compound A was obtained by column separation.
화합물 compound BB 의 제조Manufacture
화합물 A 9.2 g(31.0 mmol), Cu 2.0 g(31.0 mmol), 18-crown-6 0.4 g(1.6 mmol), K2CO3 12.8 g(93.2 mmol), 1,2-디클로로벤젠 100 mL을 섞고 180℃로 12시간동안 환류교반시켰다. 상온으로 냉각하고 감압 증류한 후 디클로로메탄으로 추출하고 증류수로 씻어주었다. MgSO4로 건조시킨 후 감압 증류하고, 컬럼 분리하여 화합물 B 7.6 g(20.4 mmol, 65.7 %)을 얻었다. Mix 9.2 g (31.0 mmol) of Compound A , 2.0 g (31.0 mmol) of Cu, 0.4 g (1.6 mmol) of 18-crown-6, 12.8 g (93.2 mmol) of K 2 CO 3 , and 100 mL of 1,2-dichlorobenzene. It was refluxed at 180 ° C. for 12 hours. After cooling to room temperature and distillation under reduced pressure, the mixture was extracted with dichloromethane and washed with distilled water. After drying over MgSO 4 , distillation under reduced pressure and column separation yielded Compound B (7.6 g, 20.4 mmol, 65.7%).
화합물 compound CC 의 제조Manufacture
화합물 B 7.6 g(20.4 mmol)을 질소 존재하에서, 테트라하이드로퓨란 250mL를 첨가한 후 -78℃로 냉각시켰다. n-뷰틸리튬(2.5M in Hexane) 12.2 mL, (30.6 mmol)을 천천히 첨가한 뒤 1시간 동안 저온을 유지하며 교반시켰다. -78℃에서 B(i-pro)3 8.8 mL(40.8 mmol)을 첨가한 뒤 1시간동안 교반시켰다. 반응이 끝나면 0℃에서 1M HCl을 첨가한 뒤 증류수로 씻어주고 에틸아세테이트로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 C 5.9 g(17.5 mmol, 86%)를 얻었다.7.6 g (20.4 mmol) of Compound B were added to 250 mL of tetrahydrofuran in the presence of nitrogen and then cooled to -78 ° C. 12.2 mL of n-butyllithium (2.5M in Hexane), (30.6 mmol) was added slowly, followed by stirring at low temperature for 1 hour. 8.8 mL (40.8 mmol) of B (i-pro) 3 was added at -78 ° C and stirred for 1 hour. After the reaction was completed, 1M HCl was added at 0 ° C, washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO 4 , the solvent was removed by rotary evaporation, and purified by column chromatography. Compound C 5.9 g (17.5 mmol, 86%).
화합물 compound DD 의 제조Manufacture
4-바이페닐아민 35.0 g(120.0 mmol), 9,9'-디메틸-2-브로모플루오렌 24.0 g(140.0 mmol), Pd(OAc)2 862 mg(3.84 mmol), P(t-Bu)3 8.5 mL(0.01 mmol), Cs2CO3 83.0 g(250.0 mmol)넣고 질소 존재하에서, 톨루엔 600 mL에 녹인 다음 120℃로 환류 교반하였다. 12시간 후 반응이 끝나면 증류수로 씻어주고 에틸아세테이트로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 D 40.0 g(110.7 mmol, 86%)를 얻었다. 35.0 g (120.0 mmol) of 4-biphenylamine, 24.0 g (140.0 mmol) of 9,9'-dimethyl-2-bromofluorene, Pd (OAc) 2 862 mg (3.84 mmol), P (t-Bu) 3 8.5 mL (0.01 mmol) and 83.0 g (250.0 mmol) of Cs 2 CO 3 were added, dissolved in 600 mL of toluene in the presence of nitrogen, followed by stirring at reflux at 120 ° C. After 12 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried over MgSO 4 and the solvent was removed using a rotary evaporator, and purified by column chromatography to obtain a compound D 40.0 g (110.7 mmol, 86%).
화합물 compound EE 의 제조Manufacture
화합물 D 20.0 g(55.3 mmol), 1,4-디브로모벤젠 26.0 g(110.0 mmol), Pd2(dba)3 1.0 g(1.1 mmol), 트리-O-톨릴포스핀(tri-o-tolyphosphine) 1.0 g(3.3 mmol), NaOt-Bu 10.6 g(110.0 mmol)를 질소 존재하에서 톨루엔 600 mL에 녹인 다음 120℃로 환류 교반하였다. 12시간 후 반응이 끝나면 증류수로 씻어주고 에틸아세테이트로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 E 17.0 g(32.9 mmol, 60%)를 얻었다.20.0 g (55.3 mmol) of compound D , 26.0 g (110.0 mmol) of 1,4-dibromobenzene, 1.0 g (1.1 mmol) of Pd 2 (dba) 3 , tri-o-tolyphosphine ) 1.0 g (3.3 mmol) and NaOt-Bu 10.6 g (110.0 mmol) were dissolved in 600 mL of toluene in the presence of nitrogen, followed by stirring at reflux at 120 ° C. After 12 hours, the reaction was washed with distilled water, extracted with ethyl acetate, the organic layer was dried with MgSO 4 and the solvent was removed using a rotary evaporator, and purified by column chromatography to obtain a compound E 17.0 g (32.9 mmol, 60%).
화합물 compound 44 의 제조Manufacture
화합물 E 10.0 g(19.4 mmol), 화합물 C 7.8 g(23.2 mmol), Pd(PPh3)4 2.2 g(1.9 mmol), K2CO3(2M) 96 mL(190 mmol), 에탄올 96 mL, 톨루엔 180 mL를 첨가한 후 120℃로 환류 교반하였다. 12시간 후 반응이 끝나면 증류수로 씻어주고 에틸아세테이트로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼크로마토그래피로 정제하여 화합물 4 10.3 g(14.1 mmol, 73%)를 얻었다. Compound E 10.0 g (19.4 mmol), Compound C 7.8 g (23.2 mmol), Pd (PPh 3 ) 4 2.2 g (1.9 mmol), K 2 CO 3 (2M) 96 mL (190 mmol), ethanol 96 mL, toluene 180 mL was added and then stirred at reflux at 120 ° C. After 12 hours, when the reaction was completed, the mixture was washed with distilled water, 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 to obtain compound 4 10.3 g (14.1 mmol, 73%).
상기 제조예 1의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 86을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다.The organic light emitting compounds 1 to 86 were prepared using the method of Preparation Example 1, and the 1 H NMR and the MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.
[표 1]TABLE 1
[실시예 1] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자의 제작Example 1 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention
본 발명의 유기 발광 화합물을 이용하여 OLED 소자를 제작하였다.An OLED device was manufactured using the organic light emitting compound of the present invention.
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? It was used after.
다음으로, 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 진공 증착 장비 내의 셀에 하기 구조의 4,4',4"-트리스(N,N-(2-나프틸)-페닐아미노)트리페닐아민(2-TNATA)을 넣고, 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 2-TNATA를 증발시켜 ITO 기판 상에 60 nm 두께의 정공주입층을 증착하였다.Next, the ITO substrate is placed in the substrate folder of the vacuum deposition equipment, and the 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) tree having the following structure is installed in the cell in the vacuum deposition equipment. Phenylamine (2-TNATA) was added and evacuated until the vacuum in the chamber reached 10 -6 torr. Then, a current was applied to the cell to evaporate 2-TNATA to inject a 60 nm thick hole injection layer onto the ITO substrate. Was deposited.
이어서, 진공 증착 장비 내의 다른 셀에 본 발명의 화합물 1을 넣고, 셀에 전류를 인가하여 화합물 1을 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.Subsequently, Compound 1 of the present invention was placed in another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate Compound 1 to deposit a 20 nm thick hole transport layer on the hole injection layer.
정공주입층 및 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 발광 재료로 호스트 재료인 4,4'-N,N'-dicarbazole-biphenyl(CBP)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.After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. 4,4'-N, N'-dicarbazole-biphenyl (CBP), a host material, is added to one cell in the vacuum deposition apparatus, and another cell is compound D having the structure A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by heating and depositing a deposition rate ratio of Compound D at 2 to 5 wt%.
이어서 상기 발광층 위에 정공차단층으로 Bis(2-methyl-8-quinolinato)Subsequently, Bis (2-methyl-8-quinolinato) is used as a hole blocking layer on the light emitting layer.
(p-phenylphenolato)aluminum(III) (BAlq)을 5 nm의 두께로 증착시키고, 전자전달층으로써 하기 구조의 트리스(8-히드록시퀴놀린)-알루미늄(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 하기 구조의 화합물 리튬 퀴놀레이트 (Liq)를 1 내지 2 nm 두께로 증착한 후, 다른 진공 증착 장비를 이용하여 Al 음극을 150 nm의 두께로 증착하여 OLED를 제작하였다. ( p- phenylphenolato) aluminum (III) (BAlq) was deposited to a thickness of 5 nm, and tris (8-hydroxyquinoline) -aluminum (III) (Alq) having the following structure was deposited to a thickness of 20 nm as an electron transport layer. Then, after depositing a compound lithium quinolate (Liq) having a structure of 1 to 2 nm thickness as an electron injection layer, using another vacuum deposition equipment to deposit an Al cathode to a thickness of 150 nm to produce an OLED.
OLED 소자에 사용된 각 재료들은, 각각 10-6 torr 하에서 진공 승화 정제하여 OLED 발광재료로 사용하였다.Each material used in the OLED device was vacuum sublimated and purified under 10 -6 torr, respectively, to be used as an OLED light emitting material.
[비교예 1]종래의 발광 재료를 이용한 OLED 소자의 발광 특성Comparative Example 1 Luminescence Characteristics of OLED Devices Using Conventional Luminescent Materials
실시예 1과 동일한 방법으로 2-TNATA를 이용하여 정공주입층을 형성시킨 후, 진공 증착 장비 내의 다른 셀에 하기구조 N,N'-비스(α-나프틸)-N,N'-디페닐-4,4'-디아민(NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.After the hole injection layer was formed by using 2-TNATA in the same manner as in Example 1, the following structures N , N' -bis (α-naphthyl) -N , N' -diphenyl were formed in other cells in the vacuum deposition equipment. -4,4'-diamine (NPB) was added, NPB was evaporated by applying a current to the cell, and a 20 nm thick hole transport layer was deposited on the hole injection layer.
그 이외에는 실시예 1과 동일한 방법으로 OLED 소자를 제작하였다. Otherwise, an OLED device was manufactured in the same manner as in Example 1.
상기 실시예 1 및 비교예 1에서 제조된 본 발명에 따른 유기 발광 화합물과 종래의 발광 화합물을 함유하는 OLED 소자의 발광 효율을 각각 1,000 cd/m2에서 측정하여 하기 표 2에 나타내었다. To the above Example 1 and Comparative Example 1, respectively, measured at 1,000 cd / m 2 light emission efficiency of the OLED device containing the organic light-emitting compound and a conventional electroluminescent compound according to the present invention in the manufacture shown in Table 2 below.
[표 2]TABLE 2
본 발명에서 개발한 화합물들이 성능 측면에서 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다.Compounds developed in the present invention was confirmed to show excellent properties compared to conventional materials in terms of performance.
[실시예 2] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자의 제작Example 2 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention
실시예 1과 동일한 방법으로 진공 증착 장비의 기판 폴더에 ITO 기판을 설치하고, 장비 내의 셀에 하기구조의 화합물 12을 넣고, 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 화합물 12를 증발시켜 ITO 기판 상에 60 nm 두께의 정공주입층을 증착하였다.In the same manner as in Example 1, an ITO substrate was placed in the substrate folder of the vacuum deposition equipment, and the compound 12 of the following structure was placed in a cell in the equipment, and evacuated until the vacuum in the chamber reached 10 -6 torr. A current was applied to the compound 12 to evaporate to deposit a 60 nm thick hole injection layer on the ITO substrate.
이어서 진공 증착 장비 내의 다른 셀에 하기구조 N,N'-비스(α-나프틸)-N,N'-디페닐-4,4'-디아민(NPB)을 넣고, 셀에 전류를 인가하여 NPB를 증발시켜 정공주입층 위에 20 nm 두께의 정공전달층을 증착하였다.Subsequently, the following structures N , N' -bis (α-naphthyl) -N , N' -diphenyl-4,4'-diamine (NPB) were added to another cell in the vacuum deposition apparatus, and NPB was applied by applying a current to the cell. Was evaporated to deposit a 20 nm thick hole transport layer on the hole injection layer.
그 이외에는 실시예 1과 동일한 방법으로 OLED 소자를 제작하였다. Otherwise, an OLED device was manufactured in the same manner as in Example 1.
상기 실시예 2 및 비교예 1에서 제조된 본 발명에 따른 유기 발광 화합물과 종래의 발광 화합물을 함유하는 OLED 소자의 발광 효율을 각각 1,000 cd/m2에서 측정하여 하기 표 3에 나타내었다. The luminous efficiency of the organic light emitting compound according to the present invention prepared in Example 2 and Comparative Example 1 and the conventional light emitting compound containing OLED is measured at 1,000 cd / m 2 are shown in Table 3 below.
[표 3][Table 3]
본 발명에서 개발한 화합물들이 성능 측면에서 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다.Compounds developed in the present invention was confirmed to show excellent properties compared to conventional materials in terms of performance.
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- 2010-03-18 CN CN2010800212132A patent/CN102449106A/en active Pending
- 2010-03-18 JP JP2012501926A patent/JP5778127B2/en not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| CN102449106A (en) | 2012-05-09 |
| TW201105770A (en) | 2011-02-16 |
| WO2010110553A2 (en) | 2010-09-30 |
| JP2012521414A (en) | 2012-09-13 |
| WO2010110553A3 (en) | 2010-12-09 |
| JP5778127B2 (en) | 2015-09-16 |
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