KR20110119206A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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Publication number
KR20110119206A
KR20110119206A KR1020100038793A KR20100038793A KR20110119206A KR 20110119206 A KR20110119206 A KR 20110119206A KR 1020100038793 A KR1020100038793 A KR 1020100038793A KR 20100038793 A KR20100038793 A KR 20100038793A KR 20110119206 A KR20110119206 A KR 20110119206A
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South Korea
Prior art keywords
alkyl
aryl
independently
heteroaryl
cycloalkyl
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KR1020100038793A
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Korean (ko)
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이효정
조영준
권혁주
김봉옥
김성민
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다우어드밴스드디스플레이머티리얼 유한회사
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Priority to KR1020100038793A priority Critical patent/KR20110119206A/en
Priority to PCT/KR2011/002489 priority patent/WO2011136482A1/en
Priority to TW100114601A priority patent/TW201204809A/en
Publication of KR20110119206A publication Critical patent/KR20110119206A/en

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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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • 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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Abstract

PURPOSE: An organic light-emitting compound is provided to ensure excellent blue luminous efficiency and excellent lifetime properties and to prepare an organic light emitting diode with excellent device driving durability. CONSTITUTION: An organic light-emitting compound is represented by chemical formula 1. An organic electroluminescent device comprises the organic light-emitting compound. The organic electroluminescent device includes a first electrode, a second electrode, and one or more organic material layers interposed between the first and second electrodes. The organic material layer comprises one or more organic luminescent compounds and one or more hosts selected from the compound of chemical formula 4: (Ar101)a-L101-(Ar102)b or chemical formula 5: (Ar103)c-L102-(Ar104)d.

Description

신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자{Novel organic electroluminescent compounds and organic electroluminescent device using the same}Novel organic electroluminescent compounds and organic electroluminescent device using the same

본 발명은 신규한 유기 발광 화합물 및 이를 포함하는 유기발광소자에 관한 것으로, 보다 구체적으로는 청색 발광 재료로서 사용되는 신규한 유기 발광 화합물 및 이를 도판트로서 채용하고 있는 유기 발광 소자에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic light emitting device comprising the same, and more particularly to a novel organic light emitting compound used as a blue light emitting material and an organic light emitting device employing the same as a dopant.

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

유기 발광 재료는 크게 고분자 재료와 저분자 재료로 나눌 수 있는데, 저분자 계열의 재료는 분자 구조 면에서 금속 착화합물과 금속을 포함하지 않는 순수 유기 발광 재료가 있다. 이러한 발광 재료로는 트리스(8-퀴놀리놀라토)알루미늄 착제 등의 킬레이트 착제, 쿠마린 유도체, 테트라페닐부타디엔 유도체, 비스스타이릴아릴렌 유도체, 옥사다이아졸 유도체 등의 발광 재료가 알려져 있고, 이들로부터는 청색에서 적색까지의 가시 영역 발광을 얻을 수 있다고 보고되었고 컬러 표시 소자의 실현이 기대되고 있다.Organic light emitting materials can be classified into high molecular materials and low molecular materials. Low molecular materials include pure organic light emitting materials that do not contain metal complexes and metals in terms of molecular structure. As such light emitting materials, light emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives are known. It has been reported that visible light emission from blue to red can be obtained and the realization of color display elements is expected.

한편, 청색 재료의 경우, 이데미쓰-고산의 DPVBi(화합물 a) 이후로 많은 재료들이 개발되어 상업화되어 있으며, 이데미쓰-고산의 청색 재료 시스템과 코닥의 디나프틸안트라센(dinaphthylanthracen, 화합물 b), 테트라(t-부틸)페릴렌(tetra(t-butyl)perlyene, 화합물 c) 시스템 등이 알려져 있으나, 아직도 많은 연구 개발이 이루어져야 할 것으로 판단된다. 현재까지 가장 효율이 좋다고 알려진 이데미쓰-고산의 디스트릴(distryl)화합물의 시스템은 파워 효율의 경우, 6 lm/W이고, 소자 수명이 30,000 시간 이상으로 좋기는 하나, 구동 시간에 따른 색순도의 저하로 인하여 풀컬러 디스플레이에 적용했을 때, 수명이 불과 수천시간에 불과하다. 청색 발광은 발광 파장이 장파장 쪽으로 조금만 이동해도 발광 효율 측면에서는 유리해지나, 순청색을 만족시키지 못해 고품위의 디스플레이에는 적용이 쉽지 않은 문제점을 갖고 있으며, 색순도, 효율 및 열안정성에 문제가 있어 연구 개발이 시급한 부분이라고 하겠다.On the other hand, in the case of blue materials, many materials have been developed and commercialized since Idemitsu-Alpine DPVBi (Compound a), and the Idemitsu-Alpine Blue Material System and Kodak's dinaphthylanthracen (Compound b), Tetra (t-butyl) perlyene (compound c) system is known, but much research and development is still required. The system of Idemitsu-high acid disryl compound, which is known to be the most efficient so far, has a power efficiency of 6 lm / W and a device life of more than 30,000 hours, but the color purity decreases with driving time. When applied to a full-color display, its lifetime is only thousands of hours. Blue light emission is advantageous in terms of luminous efficiency even if the light emission wavelength is shifted toward the longer wavelength, but it is not easy to apply to high-quality display because it does not satisfy pure blue color, and there is a problem in color purity, efficiency and thermal stability, so that research and development It is an urgent part.

Figure pat00001
Figure pat00001

따라서, 본 발명자들은 종래의 문제점을 해결하기 위하여 노력한 결과, 발광효율이 뛰어나고 수명이 획기적으로 개선된 유기발광소자를 실현하기 위한 새로운 발광화합물을 발명하게 되었다. 본 발명의 목적은 상기한 문제점들을 해결하기 위하여 기존의 도판트 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기발광화합물 및 이를 발광재료로서 채용하는 고효율 및 장수명의 유기발광소자를 제공하는 것이다. Accordingly, the present inventors have made efforts to solve the conventional problems, and have thus invented a new light emitting compound for realizing an organic light emitting device having an excellent luminous efficiency and a greatly improved lifetime. An object of the present invention is to solve the above problems, the luminous efficiency and device life is better than the conventional dopant material, excellent skeleton organic light emitting compound having a suitable color coordinate and high efficiency and long life organic light emitting device employing the same as the light emitting material To provide.

본 발명은 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자에 관한 것으로서, 본 발명에 따른 유기 발광 화합물은 하기 화학식 1로 표시되는 화합물로, 청색 발광효율이 좋고 재료의 색순도 및 수명특성이 뛰어나 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다. The present invention relates to a novel organic light emitting compound and an organic light emitting device including the same. The organic light emitting compound according to the present invention is a compound represented by the following Chemical Formula 1, and has excellent blue light emission efficiency and excellent color purity and life characteristics of a material. There is an advantage to manufacture an OLED device having a very long life.

[화학식 1][Formula 1]

Figure pat00002
Figure pat00002

[상기 화학식 1에서,[In Formula 1,

R1, R4, R7 및 R10은 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.], RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.], RdY-[Y는 O 또는 S이고, Rd는 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는

Figure pat00003
이고, 단, R1, R4, R7 및 R10 중 2개가 수소인 경우는 제외되고;R 1 , R 4 , R 7 and R 10 independently of one another are hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, ( C2-30) Heteroaryl, -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl], R a R b R c Si- [R a , R b and R c are independently of each other (C1-C30) alkyl or (C6-C30) aryl.], R d Y- [Y is O or S, and R d is (C1-C30) alkyl or ( C6-C30) aryl. Or
Figure pat00003
With the exception that two of R 1 , R 4 , R 7 and R 10 are hydrogen;

R2, R3, R5, R6, R8 및 R9는 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.], RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는 RdY-[Y는 O 또는 S이고, Rd는 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이고; R 2 , R 3 , R 5 , R 6 , R 8 and R 9 are independently of each other hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6 -30) aryl, (C2-30) heteroaryl, -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl], R a R b R c Si- [R a , R b and R c are independently of each other (C1-C30) alkyl or (C6-C30) aryl.] or R d Y- [Y is O or S, and R d is (C1 -C30) alkyl or (C6-C30) aryl.

L1은 화학결합, (C6-C30)아릴렌 또는 (C2-C30)헤테로아릴렌이고;L 1 is a chemical bond, (C6-C30) arylene or (C2-C30) heteroarylene;

L2는 (C6-C30)아릴렌, (C2-C30)헤테로아릴렌 또는

Figure pat00004
이고;L 2 is (C6-C30) arylene, (C2-C30) heteroarylene or
Figure pat00004
ego;

R11 및 R12는 서로 독립적으로 (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴 또는

Figure pat00005
이거나, 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 NR21, O 또는 S로 치환될 수 있고, R21은 수소, (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, 모폴리노, 티오모폴리노, 피페리디노, 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 할로겐, 시아노, (C6-30)아릴, (C2-30)헤테로아릴 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이고;R 11 and R 12 independently of one another are (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, (C2-30) heteroaryl or
Figure pat00005
Or a (C3-C30) alkylene or (C3-C30) alkenylene, with or without a fused ring, to form a fused ring, wherein the carbon atoms of the alkylene are substituted with NR 21 , O or S R 21 is hydrogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered Heterocycloalkyl, (C3-C30) cycloalkyl, halogen, cyano, (C6-30) aryl, (C2-30) heteroaryl or R a R b R c Si- [R a , R b and R c are Independently of one another is (C1-C30) alkyl or (C6-C30) aryl.

Z1 및 Z2는 서로 독립적으로 -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- 또는 -Si(R34)(R35)이고;Z 1 and Z 2 are independently of each other-(CR 31 R 32 ) m -,-(R 31 ) C = C (R 32 )-, -N (R 33 )-, -S-, -O-,- Se- or -Si (R 34 ) (R 35 );

R31 내지 R35은 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;R 31 to R 35 independently of one another are hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, (C2-30) heteroaryl , -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl.] Or R a R b R c Si- [R a , R b and R c Are independently (C 1 -C 30) alkyl or (C 6 -C 30) aryl], or are linked to (C 3 -C 30) alkylene or (C 3 -C 30) alkenylene with or without adjacent substituents and fused rings To form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

상기 R1 내지 R10 및 R31 내지 R35의 알킬, 사이클로알킬, 헤테로사이클로알킬, 아릴, 헤테로아릴; L1 및 L2의 아릴렌 또는 헤테로아릴렌; R11 및 R12의 사이클로알킬, 헤테로사이클로알킬, 아릴, 헤테로아릴; R11과 R12가 연결되어 형성된 융합고리는 중수소, (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알콕시, 시아노, (C1-C30)알킬실릴, (C6-C30)아릴실릴, 할로(C1-C30)알킬, (C3-C30)헤테로아릴, (C3-C30)사이클로알킬, 나이트로 및 하이드록시로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있고;Alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl of R 1 to R 10 and R 31 to R 35 ; Arylene or heteroarylene of L 1 and L 2 ; Cycloalkyl, heterocycloalkyl, aryl, heteroaryl of R 11 and R 12 ; The fused ring formed by linking R 11 and R 12 is deuterium, (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkoxy, cyano, (C1-C30) alkylsilyl, (C6-C30 May be further substituted with one or more substituents selected from arylsilyl, halo (C1-C30) alkyl, (C3-C30) heteroaryl, (C3-C30) cycloalkyl, nitro and hydroxy;

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

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

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

본 발명에 기재된 「알킬」은 탄소 원자 및 수소 원자만으로 구성된 직쇄 또는 분지쇄의 포화된 1가 탄화수소 라디칼 또는 그의 조합물을 포함한다. 본 발명에 기재된 “시클로알킬”은 단일 고리계 뿐만 아니라 아다만틸 또는 바이시클로알킬과 같은 여러 고리계 탄화수소도 포함한다."Alkyl" described in the present invention includes straight or branched chain saturated monovalent hydrocarbon radicals or combinations thereof composed of only carbon and hydrogen atoms. The "cycloalkyl" described in the present invention includes not only a single ring system but also various ring hydrocarbons such as adamantyl or bicycloalkyl.

본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐, 페난트릴, 트리페닐레닐, 피렌일, 페릴렌일, 크라이세닐, 나프타세닐, 플루오란텐일 등을 포함하지만, 이에 한정되지 않는다. 상기 나프틸은 1-나프틸 및 2-나프틸을 포함하며, 안트릴은 1-안트릴, 2-안트릴 및 9-안트릴을 포함하며, 플루오레닐은 1-플루오레닐, 2-플루오레닐, 3-플루오레닐, 4-플루오레닐 및 9-플루오레닐을 모두 포함한다. 본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠 환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연걸된 형태도 포함한다. 상기 헤테로아릴기는 고리내 헤테로원자가 산화되거나 사원화되어, 예를 들어 N-옥사이드 또는 4차 염을 형성하는 2가 아릴 그룹을 포함한다. 구체적인 예로 퓨릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 퓨라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단환 헤테로아릴, 벤조퓨란일, 벤조티오펜일, 이소벤조퓨란일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페난트리딘일, 벤조디옥솔릴 등의 다환식 헤테로아릴 및 이들의 상응하는 N-옥사이드(예를 들어, 피리딜 N-옥사이드, 퀴놀릴 N-옥사이드), 이들의 4차 염 등을 포함하지만, 이에 한정되지 않는다."Aryl" described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthasenyl, fluoranthenyl, and the like. It is not limited to this. Said naphthyl includes 1-naphthyl and 2-naphthyl, anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and fluorenyl is 1-fluorenyl, 2- Fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. The "heteroaryl" described in the present invention contains 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si, and P as aromatic ring skeleton atoms, and the remaining aromatic ring skeleton atoms are carbon. Meaning an aryl group which is 5 to 6 membered monocyclic heteroaryl, and polycyclic heteroaryl condensed with one or more benzene rings, which may be partially saturated. In addition, the heteroaryl in the present invention also includes a form in which one or more heteroaryls are linked by a single bond. Such heteroaryl groups include divalent aryl groups in which heteroatoms in the ring are oxidized or quaternized to form, for example, N-oxides or quaternary salts. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetra Monocyclic heteroaryl such as zolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothia Zolyl, Benzoisoxazolyl, Benzoxazolyl, Isoindoleyl, Indolyl, Indazolyl, Benzothiadiazolyl, Quinolyl, Isoquinolyl, Cinolinyl, Quinazolinyl, Quinoxalinyl, Carbazolyl, Phenantridinyl , Polycyclic heteroaryls such as benzodioxolyl and the like, and their corresponding N-oxides (eg, pyridyl N-oxides, quinolyl N-oxides), quaternary salts thereof, and the like. .

또한, 본 발명의 유기 발광 화합물은 하기 화학식 2 또는 3로 표시되는 화합물을 포함한다.In addition, the organic light emitting compound of the present invention includes a compound represented by the following formula (2) or (3).

[화학식 2][Formula 2]

Figure pat00006
Figure pat00006

[화학식 3](3)

Figure pat00007
Figure pat00007

[상기 화학식 2 및 3에서,[In Formula 2 and 3,

L11 및 L12은 서로 독립적으로 (C6-C30)아릴렌, (C2-C30)헤테로아릴렌 또는

Figure pat00008
이고;L 11 and L 12 independently of one another are (C6-C30) arylene, (C2-C30) heteroarylene or
Figure pat00008
ego;

L21 및 L22는 서로 독립적으로 (C6-C30)아릴렌 또는 (C2-C30)헤테로아릴렌이고;L 21 and L 22 are independently of each other (C6-C30) arylene or (C2-C30) heteroarylene;

R2, R3, R5, R6, R8 및 R9는 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴 또는 (C2-30)헤테로아릴이고; R 2 , R 3 , R 5 , R 6 , R 8 and R 9 are independently of each other hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6 -30) aryl or (C2-30) heteroaryl;

R41 내지 R44는 서로 독립적으로 (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴 또는

Figure pat00009
이거나, 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 NR21, O 또는 S로 치환될 수 있고, R21은 수소, (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, 모폴리노, 티오모폴리노, 피페리디노, 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 할로겐, 시아노, (C6-30)아릴, (C2-30)헤테로아릴 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이고;R 41 to R 44 independently of one another are (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, (C2-30) heteroaryl or
Figure pat00009
Or a (C3-C30) alkylene or (C3-C30) alkenylene, with or without a fused ring, to form a fused ring, wherein the carbon atoms of the alkylene are substituted with NR 21 , O or S R 21 is hydrogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered Heterocycloalkyl, (C3-C30) cycloalkyl, halogen, cyano, (C6-30) aryl, (C2-30) heteroaryl or R a R b R c Si- [R a , R b and R c are Independently of one another is (C1-C30) alkyl or (C6-C30) aryl.

Z1 및 Z2는 서로 독립적으로 -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- 또는 -Si(R34)(R35)이고;Z 1 and Z 2 are independently of each other-(CR 31 R 32 ) m -,-(R 31 ) C = C (R 32 )-, -N (R 33 )-, -S-, -O-,- Se- or -Si (R 34 ) (R 35 );

R31 내지 R35은 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;R 31 to R 35 independently of one another are hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, (C2-30) heteroaryl , -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl.] Or R a R b R c Si- [R a , R b and R c Are independently (C 1 -C 30) alkyl or (C 6 -C 30) aryl], or are linked to (C 3 -C 30) alkylene or (C 3 -C 30) alkenylene with or without adjacent substituents and fused rings To form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

R1, R4, R7 및 R10은 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.], RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는 RdY-[Y는 O 또는 S이고, Rd는 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이고;R 1 , R 4 , R 7 and R 10 independently of one another are hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, ( C2-30) Heteroaryl, -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl], R a R b R c Si- [R a , R b and R c are independently of each other (C1-C30) alkyl or (C6-C30) aryl.] Or R d Y- [Y is O or S, and R d is (C1-C30) alkyl or ( C6-C30) aryl.

상기 R1 내지 R10의 알킬, 사이클로알킬, 헤테로사이클로알킬, 아릴, 헤테로아릴; L11, L12, L21 및 L22의 아릴렌 또는 헤테로아릴렌은 중수소, (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알콕시, 시아노, (C1-C30)알킬실릴, (C6-C30)아릴실릴, 할로(C1-C30)알킬, (C3-C30)헤테로아릴, (C3-C30)사이클로알킬, 나이트로 및 하이드록시로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있고;Alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl of R 1 to R 10 ; The arylene or heteroarylene of L 11 , L 12 , L 21 and L 22 is deuterium, (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkoxy, cyano, (C1-C30) One or more substituents selected from alkylsilyl, (C6-C30) arylsilyl, halo (C1-C30) alkyl, (C3-C30) heteroaryl, (C3-C30) cycloalkyl, nitro and hydroxy Can;

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

상기 L11 및 L12은 서로 독립적으로 페닐렌, 나프탈렌, 바이페닐렌, 페난트릴렌, 피라지닐렌, 트리아지닐렌, 퀴놀릴렌, 페난트롤리닐렌, 티에닐렌, 퓨릴렌, 셀레노페닐렌, 티아디아졸릴렌, 옥사디아졸릴렌, 셀레나디아졸릴렌 또는 퀴녹살릴렌이거나, 하기 구조에서 선택되는 2가기이고;L 11 and L 12 are each independently phenylene, naphthalene, biphenylene, phenanthryl, pyrazinylene, triazinylene, quinolinylene, phenanthrolinylene, thienylene, purylene, selenophenylene, Thiadiazolylene, oxadiazolylene, selenadiazolylene or quinoxalylene, or a divalent group selected from the following structures;

Figure pat00010
Figure pat00010

R31 내지 R35는 서로 독립적으로 수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, 펜틸, 아밀, 헥실, 헵틸, 옥틸, 노닐, 데실, 트리플루오로메틸, 페닐, 나프틸, 바이페닐, 플루오레닐 또는 페난트릴이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고; L21 및 L22는 서로 독립적으로 페닐렌, 나프틸렌, 안트라세닐렌, 플루오레닐렌, 페난트릴렌, 비페닐렌, 트리페닐렌, 플루오란테닐렌, 크라이세닐렌, 피레닐렌, 퍼릴레닐렌, 피리디닐렌, 퓨릴렌, 티오펜일렌, 셀레노페닐렌, 피리디닐렌, 피라지닐렌, 피리다지닐렌, 퀴놀리닐렌 또는 퀴녹살리닐렌이고; R2, R3, R5, R6, R8 및 R9는 서로 독립적으로 수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, 펜틸, 아밀, 헥실, 헵틸, 옥틸, 노닐, 데실, 트리플루오로메틸, 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 사이클로옥틸, 페닐, 나프틸, 바이페닐, 플루오레닐, 페난트릴, 피리딜, 퓨릴, 티오펜일, 퀴놀릴, 아이소퀴놀릴, 페난트롤리닐, 카바졸릴, 트리아지닐 또는 피리미딜이고; R41 내지 R44는 서로 독립적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 사이클로옥틸, 페닐, 나프틸, 바이페닐, 인데닐, 플루오레닐, 벤조플루오레닐, 스피로바이플루오레닐, 안트라세닐, 피레닐, 페난트릴, 트리페닐레닐, 플루오란텐일, 피리딜, 퓨릴, 티오펜일, 퀴놀릴, 아이소퀴놀릴, 페난트롤리닐, 카바졸릴, 벤조퓨란일, 벤조티오펜일, 벤조티아졸릴, 벤조옥사졸릴, 트리아지닐 또는 피리미딜 또는

Figure pat00011
이고; R1, R4, R7 및 R10은 서로 독립적으로 수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, 펜틸, 아밀, 헥실, 헵틸, 옥틸, 노닐, 데실, 트리플루오로메틸, 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 사이클로옥틸, 페닐, 나프틸, 바이페닐, 플루오레닐, 페난트릴, 피리딜, 퓨릴, 티오펜일, 퀴놀릴, 아이소퀴놀릴, 페난트롤리닐, 카바졸릴, 트리아지닐 또는 피리미딜이고; 상기 L11, L12, L21, L22, R1 내지 R10 및 R41 내지 R44는 중수소, (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알콕시, 시아노, (C1-C30)알킬실릴, (C6-C30)아릴실릴, 할로(C1-C30)알킬, (C3-C30)헤테로아릴, (C3-C30)사이클로알킬, 나이트로 및 하이드록시로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있으며, 이에 한정되지는 않는다.R 31 to R 35 independently of one another are hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, tri Alicyclic, linked by (C3-C30) alkylene or (C3-C30) alkenylene, with or without fluoromethyl, phenyl, naphthyl, biphenyl, fluorenyl or phenanthryl A group ring and a monocyclic or polycyclic aromatic ring can be formed; L 21 and L 22 are each independently of each other phenylene, naphthylene, anthracenylene, fluorenylene, phenanthrylene, biphenylene, triphenylene, fluoranthrenylene, chrysenylene, pyrenylene, peryleneylene , Pyridinylene, furylene, thiophenylene, selenophenylene, pyridinylene, pyrazinylene, pyridazinylene, quinolinylene or quinoxalinylene; R 2 , R 3 , R 5 , R 6 , R 8 and R 9 are independently of each other hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl , Hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyri Dill, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; R 41 to R 44 independently of one another are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, indenyl, fluorenyl, benzofluorenyl, spirobiflu Orenyl, anthracenyl, pyrenyl, phenanthryl, triphenylenyl, fluoranthhenyl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, benzofuranyl, benzothiophene 1, benzothiazolyl, benzooxazolyl, triazinyl or pyrimidyl or
Figure pat00011
ego; R 1 , R 4 , R 7 and R 10 are independently of each other hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl , Nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophene 1, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; L 11 , L 12 , L 21 , L 22 , R 1 to R 10 and R 41 to R 44 are deuterium, (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkoxy, cyano , One selected from (C1-C30) alkylsilyl, (C6-C30) arylsilyl, halo (C1-C30) alkyl, (C3-C30) heteroaryl, (C3-C30) cycloalkyl, nitro and hydroxy The above substituents may be further substituted, but are not limited thereto.

상기

Figure pat00012
및
Figure pat00013
는 서로 독립적으로 하기 구조에서 선택되나, 이에 한정되지는 않는다.remind
Figure pat00012
And
Figure pat00013
Are independently selected from the following structures, but are not limited thereto.

Figure pat00014
Figure pat00014

[R31 내지 R35는 서로 독립적으로 서로 독립적으로 (C1-C60)알킬 또는 (C6-C60)아릴이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있다.]
[R 31 to R 35 are independently of each other (C 1 -C 60) alkyl or (C 6 -C 60) aryl, or (C 3 -C 30) alkylene or (C 3-with or without fused ring with adjacent substituents. C30) may be linked to alkenylene 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 light emitting compound according to the present invention may be more specifically exemplified as the following compound, but the following compound does not limit the present invention.

Figure pat00015
Figure pat00015

Figure pat00016
Figure pat00016

Figure pat00017
Figure pat00017

Figure pat00018
Figure pat00018

Figure pat00019
Figure pat00019

Figure pat00020
Figure pat00020

Figure pat00021
Figure pat00021

Figure pat00022
Figure pat00022

Figure pat00023
Figure pat00023

Figure pat00024
Figure pat00024

Figure pat00025
Figure pat00025

Figure pat00026
Figure pat00026

Figure pat00027
Figure pat00027

Figure pat00028
Figure pat00028

Figure pat00029
Figure pat00029

Figure pat00030
Figure pat00030

Figure pat00031
Figure pat00031

Figure pat00032
Figure pat00032

Figure pat00033
Figure pat00033

Figure pat00034
Figure pat00034

Figure pat00035
Figure pat00035

Figure pat00036
Figure pat00036

Figure pat00037
Figure pat00037

Figure pat00038
Figure pat00038

Figure pat00039
Figure pat00039

Figure pat00040
Figure pat00040

Figure pat00041
Figure pat00041

Figure pat00042
Figure pat00042

Figure pat00043
Figure pat00043

Figure pat00044
Figure pat00044

Figure pat00045
Figure pat00045

Figure pat00046
Figure pat00046

Figure pat00047
Figure pat00047

Figure pat00048
Figure pat00048

Figure pat00049
Figure pat00049

Figure pat00050
Figure pat00050

Figure pat00051
Figure pat00051

Figure pat00052
Figure pat00052

본 발명에 따른 유기 발광 화합물은 예를 들어 하기 반응식 1 및 2에 나타난 바와 같이, 제조될 수 있으며, 하기 반응식으로만 한정되는 것은 아니다.The organic light emitting compound according to the present invention can be prepared, for example, as shown in Schemes 1 and 2 below, but is not limited to the following scheme.

[반응식 1]Scheme 1

Figure pat00053
Figure pat00053

[반응식 2]Scheme 2

Figure pat00054
Figure pat00054

(상기 반응식 1 및 2에서 R1 내지 R10, L1, L2, R11 및 R12는 상기 화학식 1에서 정의한 바와 동일하다.)(In Reaction Schemes 1 and 2, R 1 to R 10 , L 1 , L 2 , R 11 and R 12 are the same as defined in Formula 1 above.)

또한 본 발명은 유기 발광 소자를 제공하며, 본 발명에 따른 유기 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. In another aspect, the present invention provides an organic light emitting device, the organic light emitting 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 Chemical Formula 1.

본 발명에 따른 유기 발광 소자는 상기 유기물층이 발광층을 포함하며, 상기 발광층은 상기 화학식 1 유기 발광 화합물 하나 이상을 발광 도판트로 하여 하나 이상의 호스트를 포함하는 것을 특징으로 하며, 본 발명의 유기 발광 소자에 적용되는 호스트는 특별히 제한되지 않으나, 하기 화학식 4 또는 화학식 5로 표시되는 화합물에서 선택되는 것이 바람직하다.The organic light emitting device according to the present invention is characterized in that the organic material layer includes a light emitting layer, and the light emitting layer includes at least one host by using at least one organic light emitting compound of Formula 1 as a light emitting dopant, The host applied is not particularly limited, but is preferably selected from the compounds represented by the following general formula (4) or (5).

[화학식 4][Formula 4]

(Ar101)a-L101-(Ar102)b (Ar 101 ) a -L 101- (Ar 102 ) b

[화학식 5][Chemical Formula 5]

(Ar103)c-L102-(Ar104)d (Ar 103 ) c -L 102- (Ar 104 ) d

[상기 화학식 4 및 화학식 5에서,[In Formula 4 and Formula 5,

L101는 (C6-C60)아릴렌 또는 (C4-C60)헤테로아릴렌이고;L 101 is (C6-C60) arylene or (C4-C60) heteroarylene;

L102는 안트라세닐렌이며;L 102 is anthracenylene;

Ar101 내지 Ar104은 서로 독립적으로 수소 또는 중수소이거나, (C1-C60)알킬, (C1-C60)알콕시, 할로겐, (C4-C60)헤테로아릴, (C5-C60)시클로알킬 또는 (C6-C60)아릴로부터 선택되고, 상기 Ar101 내지 Ar104의 시클로알킬, 아릴 또는 헤테로아릴은 할로겐이 치환되거나 치환되지 않은 (C1-C60)알킬, (C1-C60)알콕시, (C3-C60)시클로알킬, 할로겐, 시아노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로 이루어진 군으로부터 선택된 하나 이상이 치환되거나 치환되지 않은 (C6-C60)아릴 또는 (C4-C60)헤테로아릴, 할로겐이 치환되거나 치환되지 않은 (C1-C60)알킬, (C1-C60)알콕시, (C3-C60)시클로알킬, 할로겐, 시아노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로 이루어지는 군에서 선택되는 하나 이상의 치환기가 더 치환될 수 있고;Ar 101 to Ar 104 are independently of each other hydrogen or deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) And cycloalkyl, aryl or heteroaryl of Ar 101 to Ar 104 are (C 1 -C 60) alkyl, (C 1 -C 60) alkoxy, (C 3 -C 60) cycloalkyl, with or without halogen; One or more selected from the group consisting of halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl is unsubstituted or substituted (C6-C60) aryl or (C4-C60) heteroaryl, substituted or unsubstituted halogen, (C1-C60) alkyl, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri One or more substituents selected from the group consisting of (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted And;

a, b, c 및 d는 독립적으로 0 내지 4의 정수이다.]a, b, c and d are independently integers from 0 to 4.

상기 발광층의 의미는 발광이 이루어지는 층으로서 단일 층일 수 있으며, 또한 2개 이상의 층이 적층된 복수의 층일 수 있다. 본 발명의 구성에서의 호스트-도판트를 혼합하여 사용하는 경우, 본 발명의 발광 호스트에 의한 발광 효율의 현저한 개선을 확인할 수 있었다. 이는 0.5 내지 10중량%의 도핑 농도로 구성할 수 있는데, 기존의 다른 호스트 재료에 비하여 정공, 전자에 대한 전도성이 매우 뛰어나며, 물질 안정성을 매우 우수하여 발광효율 뿐만 아니라, 수명도 현저히 개선시키는 특성을 보여 주고 있다. 따라서, 상기 화학식 4 또는 5로부터 선택되는 화합물을 발광 호스트로 채택하는 경우, 본 발명의 화학식 1의 유기 발광 화합물의 전기적 단점을 상당히 보완해 주는 역할을 하고 있다고 설명할 수 있다.The light emitting layer may be a single layer as a light emitting layer, or may be a plurality of layers in which two or more layers are stacked. In the case of using a mixture of the host and dopants in the configuration of the present invention, a significant improvement in the luminous efficiency by the light emitting host of the present invention was confirmed. It can be composed of a doping concentration of 0.5 to 10% by weight, and has excellent conductivity for holes and electrons compared to other host materials, and has excellent material stability, which significantly improves luminous efficiency and lifetime. Is showing. Therefore, when the compound selected from Chemical Formula 4 or 5 is adopted as a light emitting host, it can be described that it plays a role of substantially complementing the electrical shortcomings of the organic light emitting compound of Chemical Formula 1 of the present invention.

본 발명의 유기 발광 소자에 있어서, 화학식 1의 유기 발광 화합물을 포함하고, 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있으며, 아릴아민계 화합물 또는 스티릴아릴아민계 화합물의 구체적인 예는 특허출원 제10-2008-0060393호의 식별번호<212> 내지 <224>에 예시되어 있으며, 이에 한정되는 것은 아니다.
In the organic light emitting device of the present invention, an organic light emitting compound of Formula 1, and at the same time may include one or more compounds selected from the group consisting of arylamine-based compounds or styrylarylamine-based compounds, arylamine-based compounds or Specific examples of the styrylarylamine compound are exemplified in the identification numbers <212> to <224> of Patent Application No. 10-2008-0060393, but are not limited thereto.

또한, 본 발명의 유기 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 금속을 더 포함할 수도 있고, 상기 유기물층은 발광층 및 전하생성층을 포함할 수 있다.In addition, in the organic light emitting device of the present invention, in the organic layer, in addition to the organic light emitting compound of Formula 1, from the group consisting of Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanide series metal and organic metal of d-transition element The organic material layer may further include one or more selected metals, and the organic material layer may include a light emitting layer and a charge generating layer.

본 발명의 화학식 1의 유기 발광 화합물을 포함하는 유기 발광 소자를 서브픽셀로 하고, Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au 및 Ag로 이루어진 군에서 선택되는 하나 이상의 금속화합물을 포함하는 서브픽셀 하나 이상을 동시에 병렬로 패터닝한 독립발광방식의 픽셀구조를 가진 유기 발광 소자를 구현할 수도 있다.An organic light emitting device including the organic light emitting compound of Formula 1 of the present invention is a subpixel, and includes Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag. An organic light emitting device having an independent light emitting pixel structure in which at least one subpixel including at least one metal compound selected from the group consisting of at least one metal is simultaneously patterned in parallel may be implemented.

또한, 상기 유기물층에 상기 유기 발광 화합물 이외에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 발광 소자를 형성할 수 있다.In addition, an organic light emitting device that emits white light may be formed in the organic material layer by simultaneously including one or more organic light emitting layers emitting blue, red, or green light in addition to the organic light emitting compound.

본 발명의 유기 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 있다.In the organic light emitting device of the present invention, at least one inner surface of the pair of electrodes includes at least one layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer (hereinafter, these are referred to as "surface layers"). It is preferable to arrange. 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 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 발광 소자를 제작할 수 있다.Further, in the organic light emitting device of the present invention, it is also preferable to arrange a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transfer compound and the oxidative dopant on at least one surface of the pair of electrodes thus produced. Do. 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, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generation layer.

본 발명에 따른 유기 발광화합물은 청색의 발광효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 양호한 OLED 소자를 제조할 수 있는 장점이 있다.The organic light emitting compound according to the present invention has an advantage of producing an OLED device having a good luminous efficiency of blue and excellent life characteristics of the material and having a very good 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 2의 제조Preparation Example 1 Preparation of Compound 2

Figure pat00055
Figure pat00055

화합물 F의 제조Preparation of Compound F

화합물 D 10g(16.99mmol)을 THF 100ml에 녹이고 -78℃에서 n-buLi 50.99ml(20.39mmol, 2.5M in hex)을 천천히 넣는다. 한시간 교반 후 DMF 3.2ml(54.39mmol)을 넣는다. 온도를 천천히 올리고 실온에서 12시간 교반한다. 증류수를 넣고 MC 로 추출한다. 황산 마그네슘으로 건조하고 감압 증류한다. 컬럼 분리하여 화합물 F 4.7g(9.65mmol, 56.85%)을 얻었다. Dissolve 10 g (16.99 mmol) of Compound D in 100 ml of THF and slowly add 50.99 ml (20.39 mmol, 2.5 M in hex) of n-buLi at -78 ° C. After stirring for an hour, 3.2 ml (54.39 mmol) of DMF were added. Slowly raise the temperature and stir at room temperature for 12 hours. Add distilled water and extract with MC. Dry with magnesium sulfate and distillation under reduced pressure. Compound F 4.7g (9.65mmol, 56.85%) was obtained by column separation.

화합물 H의 제조Preparation of Compound H

화합물 G 26g(95.12mmol)과 NaBH4 5.39g(142.68mmol)을 THF 300ml와 혼합한다. 0℃에서 메탄올을 천천히 넣고, 2시간 후 EA로 추출하고 증류수로 씻어준다. 황산 마그네슘으로 건조하고 컬럼분리하여 화합물 H 26g(94.42mmol(99.27%)을 얻었다. 26 g (95.12 mmol) of compound G and 5.39 g (142.68 mmol) of NaBH 4 are mixed with 300 ml of THF. Methanol is added slowly at 0 ° C., extracted with EA and washed with distilled water after 2 hours. Drying with magnesium sulfate and column separation yielded Compound H 26g (94.42mmol (99.27%)).

화합물 I의 제조Preparation of Compound I

화합물 H 26g(94.42mmol)을 트리에틸포스파이트 100ml에 녹이고 아이오딘 23.96g(94.42mmol)을 트리에틸포스파이트 50ml에 녹인다. 상기 두 용액을 천천히 혼합하고, 100℃로 교반한다. 12시간 후 실온으로 냉각하고 감압 증류한다. MC로 추출하고 증류수로 씻어준다. 황산 마그네슘으로 건조하고 감압 증류하고 컬럼분리하여 화합물 I 32g(80.92mmol, 86.09%)를 얻었다. 26 g (94.42 mmol) of Compound H are dissolved in 100 ml of triethyl phosphite, and 23.96 g (94.42 mmol) of iodine is dissolved in 50 ml of triethyl phosphite. The two solutions are slowly mixed and stirred at 100 ° C. After 12 hours, the mixture was cooled to room temperature and distilled under reduced pressure. Extract with MC and wash with distilled water. Drying with magnesium sulfate, distillation under reduced pressure and column separation yielded 32 g (80.92 mmol, 86.09%) of compound I.

화합물 2의 제조Preparation of Compound 2

화합물 F 4.7g(9.65mmol)와 화합물 I 7.63g(19.3mmol)을 THF 50ml에 녹이고 포타슘 tert-부톡사이드 24ml(24.12mmol, 1.0M in THF)을 0℃에서 가한다. 2시간 후 증류수를 넣고 MC로 추출한다. 황산마그네슘으로 건조하고 감압 증류한다. 컬럼분리하여 화합물 2 4.3g(4.43mmol, 45.97%)를 얻었다.4.7 g (9.65 mmol) of Compound F and 7.63 g (19.3 mmol) of Compound I are dissolved in 50 ml of THF, and 24 ml (24.12 mmol, 1.0 M in THF) of potassium tert-butoxide is added at 0 ° C. After 2 hours, distilled water was added and extracted with MC. Dry over magnesium sulfate and distillation under reduced pressure. Compound 2 (4.3g, 4.43mmol, 45.97%) was obtained by column separation.

[제조예 2] 화합물 101의 제조Preparation Example 2 Preparation of Compound 101

Figure pat00056
Figure pat00056

화합물 L의 제조Preparation of Compound L

디페닐아민 20g(118.2mmol), 화합물 k 24.04g(130.02mmol), Pd(OAc)2 1.3g(5.91mmol), 세슘 카보네이트 96.2g(295.50mmol)와 톨루엔 500ml를 섞고 트리-t-부틸포스핀 5.8ml(11.82mmol, in 50% xylene)을 넣고 120℃에서 교반한다. 10시간 후 실온으로 냉각하고 증류수를 넣고 EA로 추출한다. 황산 마그네슘으로 건조하고 감압 증류한다. 컬럼 분리하여 화합물 L 14.7g(53.58mmol, 45.41%)을 얻었다. 20 g (118.2 mmol) of diphenylamine, compound k 24.04 g (130.02 mmol), 1.3 g (5.91 mmol) of Pd (OAc) 2 , 96.2 g (295.50 mmol) of cesium carbonate and 500 ml of toluene were mixed and tri-t-butylphosphine Add 5.8 ml (11.82 mmol, in 50% xylene) and stir at 120 ° C. After 10 hours, cooled to room temperature, distilled water was added and extracted with EA. Dry with magnesium sulfate and distillation under reduced pressure. Compound L (14.7g, 53.58mmol, 45.41%) was obtained by column separation.

화합물 101의 제조Preparation of Compound 101

화합물 L을 중간체로 사용해서 제조예 1과 동일한 방법으로 화합물 101 3g (32%)을 얻었다.
Using compound L as an intermediate, compound 101 3 g (32%) was obtained in the same manner as in Preparation Example 1.

[제조예 3] 화합물 106의 제조Preparation Example 3 Preparation of Compound 106

Figure pat00057
Figure pat00057

화합물 M의 제조Preparation of Compound M

둥근 바닥 플라스크에 4-브로모톨루엔 6.8ml(55.2mmol)을 넣고 진공 건조 시킨 후 질소가스를 채운다. THF 200ml를 위 플라스크에 넣어 화합물을 녹인 뒤 -78℃로 냉각시킨다. n-부틸리튬 22ml(55.2mmol)을 위 플라스크에 천천히 첨가한 뒤 1시간 동안 저온을 유지하며 교반한다. 1시간 후 -78℃에서 페난트렌퀴논 5g (24mmol)을 첨가한 뒤 서서히 실온으로 올리며 3시간 동안 교반한다. 반응이 끝나면 에틸에테르로 추출한 뒤 황산 마그네슘으로 남은 수분을 제거하고 건조시킨다. 얻어진 물질을 컬럼 분리하여 화합물 M 5.9g (14.8mmol, 63%)을 얻었다.Put 6.8ml (55.2mmol) of 4-bromotoluene in the round bottom flask, vacuum dry and fill with nitrogen gas. 200 ml of THF was added to the above flask to dissolve the compound and cooled to -78 ° C. 22 ml (55.2 mmol) of n-butyllithium are slowly added to the flask and stirred at low temperature for 1 hour. After 1 hour, 5 g (24 mmol) of phenanthrenequinone was added at -78 ° C, and then slowly raised to room temperature and stirred for 3 hours. After the reaction, the mixture was extracted with ethyl ether, dried over magnesium sulfate and dried. Compound M (5.9g, 14.8mmol, 63%) was obtained by column separation of the obtained material.

화합물 N의 제조Preparation of Compound N

둥근 바닥 플라스크에 화합물 M 5g(12.6mmol)를 AcOH 100ml에 녹여 환류시키고 Zn 분말 4g(63mmol)을 첨가한다. AcOH 12ml에 HCl 2.5ml을 녹여 위 플라스크에 첨가한다. 30분 후 또다시 Zn 분말 4g(63mmol)과 AcOH 12ml에 HCl 2.5ml을 녹여 첨가한다. TLC에서 반응이 더 이상 진행되지 않을 때 까지 환류시킨다. MC, 증류수, 소듐 바이카보네이트 수용액과 NaCl 수용액으로 추출한 뒤 황산 마그네슘으로 남은 수분을 제거하고 건조시킨다. 얻어진 물질을 컬럼 분리하여 화합물 N 4.3g(11.9mmol, 97%)을 얻었다.In a round bottom flask, 5 g (12.6 mmol) of Compound M was dissolved in 100 ml of AcOH and refluxed, and 4 g (63 mmol) of Zn powder were added. Dissolve 2.5 ml of HCl in 12 ml of AcOH and add to the flask. After 30 minutes, 4 g (63 mmol) of Zn powder and 2.5 ml of HCl were added to 12 ml of AcOH. Reflux until TLC no longer proceeds. After extracting with MC, distilled water, aqueous sodium bicarbonate solution and aqueous NaCl solution, the remaining water with magnesium sulfate is removed and dried. The obtained material was separated by column to obtain 4.3 g (11.9 mmol, 97%) of compound N.

화합물 O의 제조Preparation of Compound O

둥근 바닥 플라스크에 화합물 N 5.8g(16.1mmol), NBS 6.6g(37mmol)과 벤조일퍼옥사이드 391mg(1.61mmol)을 넣고 진공 건조시킨 후 질소가스를 채운다. CCl4 193ml를 위 플라스크에 넣어 화합물을 녹인 후 4시간 동안 환류시킨다. 반응이 끝나면 MC로 추출한 뒤 황산 마그네슘으로 남은 수분을 제거하여 건조시키고 바로 다음 반응으로 진행한다. Put a compound N 5.8g (16.1mmol), NBS 6.6g (37mmol) and benzoyl peroxide 391mg (1.61mmol) in a round bottom flask and vacuum dried and filled with nitrogen gas. 193 ml of CCl 4 is added to the flask and the compound is refluxed for 4 hours. After the reaction, the extract is extracted with MC and dried with magnesium sulfate to remove the remaining water and proceeds to the next reaction.

화합물 P의 제조Preparation of Compound P

둥근 바닥 플라스크에 화합물 O 11g(21.3mmol)을 넣고 진공 건조시킨 후 질소가스를 채운다. 트리에틸포스파이트 40ml를 위 플라스크에 넣어 화합물을 녹인 후 7시간 동안 환류 시킨다. 반응이 끝나면 디스틸 장치로 트리에틸포스파이트를 제거하고 컬럼분리하여 화합물 P 12.2g(19.3mmol, 91%)을 얻었다.11 g (21.3 mmol) of Compound O was added to a round bottom flask, followed by vacuum drying, followed by nitrogen gas. 40 ml of triethyl phosphite was added to the flask to dissolve the compound and refluxed for 7 hours. After the reaction, triethyl phosphite was removed using a distillation apparatus, and column separation was performed to obtain Compound P 12.2 g (19.3 mmol, 91%).

화합물 106의 제조Preparation of Compound 106

둥근 바닥 플라스크에 화합물 P 3g(4.75mmol)와 4-(디페닐아미노)벤즈알데히드 3.1g(11.4mmol)을 넣고 진공 건조시킨 뒤 질소가스를 채운다. THF 200ml을 위 플라스크에 넣어 화합물을 녹이고 0℃로 냉각시킨 뒤 포타슘-tert-부톡사이드 57ml(57mmol)을 천천히 첨가하고 10분간 교반한다. 온도를 실온으로 올린 뒤 1시간 동안 교반한다. 반응이 끝나면 EA로 추출하고 황산 마그네슘으로 남은 수분을 제거하여 건조시킨다. 얻어진 물질을 컬럼분리하여 화합물 106 2g(2.3mmol, 50%)을 얻었다.3 g (4.75 mmol) of compound P and 3.1 g (11.4 mmol) of 4- (diphenylamino) benzaldehyde were added to a round bottom flask, followed by vacuum drying and filling with nitrogen gas. 200 ml of THF was added to the above flask to dissolve the compound, cooled to 0 ° C., and 57 ml (57 mmol) of potassium-tert-butoxide was slowly added and stirred for 10 minutes. Raise the temperature to room temperature and stir for 1 hour. After the reaction, the mixture is extracted with EA, dried with magnesium sulfate and dried. The obtained material was separated by column to obtain 2 g (2.3 mmol, 50%) of compound 106 .

상기 제조예 1 내지 3의 방법을 이용하여 유기 발광 화합물 1 내지 화합물 111을 제조하였으며, 표 1에 제조된 유기 발광 화합물들의 1H NMR 및 MS/FAB를 나타내었다. The organic light emitting compounds 1 to 111 were prepared using the methods of Preparation Examples 1 to 3, and 1 H NMR and MS / FAB of the organic light emitting compounds prepared in Table 1 are shown.

[표 1]TABLE 1

Figure pat00058
Figure pat00058

Figure pat00059
Figure pat00059

Figure pat00060
Figure pat00060

Figure pat00061
Figure pat00061

Figure pat00062
Figure pat00062

Figure pat00063
Figure pat00063

Figure pat00064
Figure pat00064

[실시예 1-11] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작[Example 1-11] OLED device fabrication using 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 셀에4,4',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.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 Ω / □) obtained from an OLED glass (manufactured by Samsung Corning Corporation) was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol. It was used after. 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. After the evacuation and evacuation until the vacuum in the chamber reached 10 −6 torr, a current was applied to the cell to evaporate 2-TNATA to deposit a 60 nm thick hole injection layer on the ITO substrate.

이어서, 진공 증착 장비 내의 다른 셀에 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.Then, to another cell of the vacuum vapor-deposit device N, N '-bis (α- naphthyl) - N, N' into the -diphenyl-4,4'-diamine (NPB) , and evaporation of the NPB by applying a current to the cell A 20 nm thick hole transport layer was deposited on the hole injection layer.

정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 하기 구조의 DNA(실시예 1 내지 3)를 넣고, 또 다른 셀에는 도판트로서 본 발명에 따른 화합물을 각각 넣은 후, 증착 속도를 100:3 로 하여 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. DNA (Examples 1 to 3) having the following structure as a host was put into one cell in a vacuum deposition apparatus, and the compound according to the present invention was put into another cell as a dopant, and then the deposition rate was 100: 3. A 30 nm thick light emitting layer was deposited on the transfer layer.

Figure pat00065
Figure pat00065

이어서 전자전달층으로써 tris(8-hydroxyquinoline)-aluminum(III) (Alq)를 20 nm 두께로 증착한 다음, 전자주입층으로 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, tris (8-hydroxyquinoline) -aluminum (III) (Alq) was deposited to a thickness of 20 nm as an electron transport layer, and then a compound lithium quinolate (Liq) was deposited to a thickness of 1 to 2 nm using an electron injection layer. An OLED was manufactured by depositing an Al cathode to a thickness of 150 nm using a vacuum deposition apparatus.

재료 별로 각 화합물은 10-6torr 하에서 진공승화 정제하여 OLED 발광재료로 사용하였다.
For each material, each compound was used as an OLED light emitting material by vacuum sublimation purification under 10 -6 torr.

상기 실시예 1 내지 3에서 제조된 본 발명에 따른 유기 발광 화합물을 함유하는 OLED 소자의 발광 효율을 각각 1,000 cd/m2에서 측정하여 하기 표 2에 나타내었다.The luminous efficiency of the OLED device containing the organic light emitting compound according to the present invention prepared in Examples 1 to 3 was measured at 1,000 cd / m 2 , respectively, and is shown in Table 2 below.

[표 2]TABLE 2

Figure pat00066
Figure pat00066

상기 표 2에 나타난 바와 같이, 본 발명의 유기 발광 화합물들은 진한 청색을 구현할 수 있음을 알 수 있었다. 즉, 유기 발광 디스플레이에서 NTSC에 근접한 색을 구현하기 위하여 CIE y = 0.1 정도의 청색이 필요할 때 본 발명의 유기 발광 화합물이 유용하게 쓰일 수 있다. 또한 페난트렌 유도체는 유리전이온도가 높아 열적 안정성이 뛰어난 장점이 있다. 이상에서와 같이 본 발명의 유기 발광 화합물은 고순도의 청색 발광 재료로 사용될 수 있음을 확인하였다. As shown in Table 2, it was found that the organic light emitting compounds of the present invention can implement a dark blue color. That is, the organic light emitting compound of the present invention may be useful when a blue color of CIE y = 0.1 is required in order to realize a color close to NTSC in the organic light emitting display. In addition, the phenanthrene derivative has an advantage of excellent thermal stability due to its high glass transition temperature. As described above, it was confirmed that the organic light emitting compound of the present invention can be used as a high purity blue light emitting material.

Claims (10)

하기 화학식 1로 표시되는 유기발광화합물.
[화학식 1]
Figure pat00067

[상기 화학식 1에서,
R1, R4, R7 및 R10은 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.], RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.], RdY-[Y는 O 또는 S이고, Rd는 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는
Figure pat00068
이고, 단, R1, R4, R7 및 R10 중 2개가 수소인 경우는 제외되고;
R2, R3, R5, R6, R8 및 R9는 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.], RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는 RdY-[Y는 O 또는 S이고, Rd는 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이고;
L1은 화학결합, (C6-C30)아릴렌 또는 (C2-C30)헤테로아릴렌이고;
L2는 (C6-C30)아릴렌, (C2-C30)헤테로아릴렌 또는
Figure pat00069
이고;
R11 및 R12는 서로 독립적으로 (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴 또는
Figure pat00070
이거나, 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 NR21, O 또는 S로 치환될 수 있고, R21은 수소, (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, 모폴리노, 티오모폴리노, 피페리디노, 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 할로겐, 시아노, (C6-30)아릴, (C2-30)헤테로아릴 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이고;
Z1 및 Z2는 서로 독립적으로 -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- 또는 -Si(R34)(R35)이고;
R31 내지 R35은 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;
상기 R1 내지 R10 및 R31 내지 R35의 알킬, 사이클로알킬, 헤테로사이클로알킬, 아릴, 헤테로아릴; L1 및 L2의 아릴렌 또는 헤테로아릴렌; R11 및 R12의 사이클로알킬, 헤테로사이클로알킬, 아릴, 헤테로아릴; R11과 R12가 연결되어 형성된 융합고리는 중수소, (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알콕시, 시아노, (C1-C30)알킬실릴, (C6-C30)아릴실릴, 할로(C1-C30)알킬, (C3-C30)헤테로아릴, (C3-C30)사이클로알킬, 나이트로 및 하이드록시로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있고;
상기 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하며;
m은 0, 1 또는 2의 정수이다.]An organic light emitting compound represented by the following formula (1).
[Formula 1]
Figure pat00067

[In the above formula (1)
R 1 , R 4 , R 7 and R 10 independently of one another are hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, ( C2-30) Heteroaryl, -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl], R a R b R c Si- [R a , R b and R c are independently of each other (C1-C30) alkyl or (C6-C30) aryl.], R d Y- [Y is O or S, and R d is (C1-C30) alkyl or ( C6-C30) aryl. Or
Figure pat00068
With the exception that two of R 1 , R 4 , R 7 and R 10 are hydrogen;
R 2 , R 3 , R 5 , R 6 , R 8 and R 9 are independently of each other hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6 -30) aryl, (C2-30) heteroaryl, -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl], R a R b R c Si- [R a , R b and R c are independently of each other (C1-C30) alkyl or (C6-C30) aryl.] or R d Y- [Y is O or S, and R d is (C1 -C30) alkyl or (C6-C30) aryl.
L 1 is a chemical bond, (C6-C30) arylene or (C2-C30) heteroarylene;
L 2 is (C6-C30) arylene, (C2-C30) heteroarylene or
Figure pat00069
ego;
R 11 and R 12 independently of one another are (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, (C2-30) heteroaryl or
Figure pat00070
Or a (C3-C30) alkylene or (C3-C30) alkenylene, with or without a fused ring, to form a fused ring, wherein the carbon atoms of the alkylene are substituted with NR 21 , O or S R 21 is hydrogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered Heterocycloalkyl, (C3-C30) cycloalkyl, halogen, cyano, (C6-30) aryl, (C2-30) heteroaryl or R a R b R c Si- [R a , R b and R c are Independently of one another is (C1-C30) alkyl or (C6-C30) aryl.
Z 1 and Z 2 are independently of each other-(CR 31 R 32 ) m -,-(R 31 ) C = C (R 32 )-, -N (R 33 )-, -S-, -O-,- Se- or -Si (R 34 ) (R 35 );
R 31 to R 35 independently of one another are hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, (C2-30) heteroaryl , -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl.] Or R a R b R c Si- [R a , R b and R c Are independently (C 1 -C 30) alkyl or (C 6 -C 30) aryl], or are linked to (C 3 -C 30) alkylene or (C 3 -C 30) alkenylene with or without adjacent substituents and fused rings To form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
Alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl of R 1 to R 10 and R 31 to R 35 ; Arylene or heteroarylene of L 1 and L 2 ; Cycloalkyl, heterocycloalkyl, aryl, heteroaryl of R 11 and R 12 ; The fused ring formed by linking R 11 and R 12 is deuterium, (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkoxy, cyano, (C1-C30) alkylsilyl, (C6-C30 May be further substituted with one or more substituents selected from arylsilyl, halo (C1-C30) alkyl, (C3-C30) heteroaryl, (C3-C30) cycloalkyl, nitro and hydroxy;
The heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P;
m is an integer of 0, 1 or 2.] 제 1항에 있어서,
하기 화학식 2 또는 3으로 표시되는 유기발광화합물.
[화학식 2]
Figure pat00071

[화학식 3]
Figure pat00072

[상기 화학식 2 및 3에서,
L11 및 L12은 서로 독립적으로 (C6-C30)아릴렌, (C2-C30)헤테로아릴렌 또는
Figure pat00073
이고;
L21 및 L22는 서로 독립적으로 (C6-C30)아릴렌 또는 (C2-C30)헤테로아릴렌이고;
R2, R3, R5, R6, R8 및 R9는 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴 또는 (C2-30)헤테로아릴이고;
R41 내지 R44는 서로 독립적으로 (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴 또는
Figure pat00074
이거나, 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 융합고리를 형성할 수 있으며, 상기 알킬렌의 탄소원자는 NR21, O 또는 S로 치환될 수 있고, R21은 수소, (C1-C30)알킬, 할로(C1-C30)알킬, (C1-C30)알콕시, 모폴리노, 티오모폴리노, 피페리디노, 5원 내지 7원의 헤테로사이클로알킬, (C3-C30)사이클로알킬, 할로겐, 시아노, (C6-30)아릴, (C2-30)헤테로아릴 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이고;
Z1 및 Z2는 서로 독립적으로 -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- 또는 -Si(R34)(R35)이고;
R31 내지 R35은 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는 RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있으며;
R1, R4, R7 및 R10은 서로 독립적으로 수소, (C1-C30)알킬, (C3-C30)사이클로알킬, 5원 내지 7원의 헤테로사이클로알킬, (C6-30)아릴, (C2-30)헤테로아릴, -NReRf[Re 및 Rf는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.], RaRbRcSi-[Ra, Rb 및 Rc는 서로 독립적으로 (C1-C30)알킬 또는 (C6-C30)아릴이다.] 또는 RdY-[Y는 O 또는 S이고, Rd는 (C1-C30)알킬 또는 (C6-C30)아릴이다.]이고;
상기 R1 내지 R10의 알킬, 사이클로알킬, 헤테로사이클로알킬, 아릴, 헤테로아릴; L11, L12, L21 및 L22의 아릴렌 또는 헤테로아릴렌은 중수소, (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알콕시, 시아노, (C1-C30)알킬실릴, (C6-C30)아릴실릴, 할로(C1-C30)알킬, (C3-C30)헤테로아릴, (C3-C30)사이클로알킬, 나이트로 및 하이드록시로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있고;
m은 0, 1 또는 2의 정수이다.]The method of claim 1,
An organic light emitting compound represented by the following formula (2) or (3).
(2)
Figure pat00071

(3)
Figure pat00072

[In Formula 2 and 3,
L 11 and L 12 independently of one another are (C6-C30) arylene, (C2-C30) heteroarylene or
Figure pat00073
ego;
L 21 and L 22 are independently of each other (C6-C30) arylene or (C2-C30) heteroarylene;
R 2 , R 3 , R 5 , R 6 , R 8 and R 9 are independently of each other hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6 -30) aryl or (C2-30) heteroaryl;
R 41 to R 44 independently of one another are (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, (C2-30) heteroaryl or
Figure pat00074
Or a (C3-C30) alkylene or (C3-C30) alkenylene, with or without a fused ring, to form a fused ring, wherein the carbon atoms of the alkylene are substituted with NR 21 , O or S R 21 is hydrogen, (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered Heterocycloalkyl, (C3-C30) cycloalkyl, halogen, cyano, (C6-30) aryl, (C2-30) heteroaryl or R a R b R c Si- [R a , R b and R c are Independently of one another is (C1-C30) alkyl or (C6-C30) aryl.
Z 1 and Z 2 are independently of each other-(CR 31 R 32 ) m -,-(R 31 ) C = C (R 32 )-, -N (R 33 )-, -S-, -O-,- Se- or -Si (R 34 ) (R 35 );
R 31 to R 35 independently of one another are hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, (C2-30) heteroaryl , -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl.] Or R a R b R c Si- [R a , R b and R c Are independently (C 1 -C 30) alkyl or (C 6 -C 30) aryl], or are linked to (C 3 -C 30) alkylene or (C 3 -C 30) alkenylene with or without adjacent substituents and fused rings To form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
R 1 , R 4 , R 7 and R 10 independently of one another are hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30) aryl, ( C2-30) Heteroaryl, -NR e R f [R e and R f are independently of each other (C1-C30) alkyl or (C6-C30) aryl], R a R b R c Si- [R a , R b and R c are independently of each other (C1-C30) alkyl or (C6-C30) aryl.] Or R d Y- [Y is O or S, and R d is (C1-C30) alkyl or ( C6-C30) aryl.
Alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl of R 1 to R 10 ; The arylene or heteroarylene of L 11 , L 12 , L 21 and L 22 is deuterium, (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkoxy, cyano, (C1-C30) One or more substituents selected from alkylsilyl, (C6-C30) arylsilyl, halo (C1-C30) alkyl, (C3-C30) heteroaryl, (C3-C30) cycloalkyl, nitro and hydroxy Can;
m is an integer of 0, 1 or 2.] 제 2항에 있어서,
L11 및 L12은 서로 독립적으로 페닐렌, 나프탈렌, 바이페닐렌, 페난트릴렌, 피라지닐렌, 트리아지닐렌, 퀴놀릴렌, 페난트롤리닐렌, 티에닐렌, 퓨릴렌, 셀레노페닐렌, 티아디아졸릴렌, 옥사디아졸릴렌, 셀레나디아졸릴렌 또는 퀴녹살릴렌이거나, 하기 구조에서 선택되는 2가기이고;
Figure pat00075

R31 내지 R35는 서로 독립적으로 수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, 펜틸, 아밀, 헥실, 헵틸, 옥틸, 노닐, 데실, 트리플루오로메틸, 페닐, 나프틸, 바이페닐, 플루오레닐 또는 페난트릴이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있고; L21 및 L22는 서로 독립적으로 페닐렌, 나프틸렌, 안트라세닐렌, 플루오레닐렌, 페난트릴렌, 비페닐렌, 트리페닐렌, 플루오란테닐렌, 크라이세닐렌, 피레닐렌, 퍼릴레닐렌, 피리디닐렌, 퓨릴렌, 티오펜일렌, 셀레노페닐렌, 피리디닐렌, 피라지닐렌, 피리다지닐렌, 퀴놀리닐렌 또는 퀴녹살리닐렌이고; R2, R3, R5, R6, R8 및 R9는 서로 독립적으로 수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, 펜틸, 아밀, 헥실, 헵틸, 옥틸, 노닐, 데실, 트리플루오로메틸, 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 사이클로옥틸, 페닐, 나프틸, 바이페닐, 플루오레닐, 페난트릴, 피리딜, 퓨릴, 티오펜일, 퀴놀릴, 아이소퀴놀릴, 페난트롤리닐, 카바졸릴, 트리아지닐 또는 피리미딜이고; R41 내지 R44는 서로 독립적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 사이클로옥틸, 페닐, 나프틸, 바이페닐, 인데닐, 플루오레닐, 벤조플루오레닐, 스피로바이플루오레닐, 안트라세닐, 피레닐, 페난트릴, 트리페닐레닐, 플루오란텐일, 피리딜, 퓨릴, 티오펜일, 퀴놀릴, 아이소퀴놀릴, 페난트롤리닐, 카바졸릴, 벤조퓨란일, 벤조티오펜일, 벤조티아졸릴, 벤조옥사졸릴, 트리아지닐 또는 피리미딜 또는
Figure pat00076
이고; R1, R4, R7 및 R10은 서로 독립적으로 수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, 펜틸, 아밀, 헥실, 헵틸, 옥틸, 노닐, 데실, 트리플루오로메틸, 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 사이클로옥틸, 페닐, 나프틸, 바이페닐, 플루오레닐, 페난트릴, 피리딜, 퓨릴, 티오펜일, 퀴놀릴, 아이소퀴놀릴, 페난트롤리닐, 카바졸릴, 트리아지닐 또는 피리미딜이고; 상기 L11, L12, L21, L22, R1 내지 R10 및 R41 내지 R44는 중수소, (C1-C30)알킬, (C6-C30)아릴, (C1-C30)알콕시, 시아노, (C1-C30)알킬실릴, (C6-C30)아릴실릴, 할로(C1-C30)알킬, (C3-C30)헤테로아릴, (C3-C30)사이클로알킬, 나이트로 및 하이드록시로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있는 것을 특징으로 하는 유기 발광 화합물.The method of claim 2,
L 11 and L 12 are independently of each other phenylene, naphthalene, biphenylene, phenanthryl, pyrazinylene, triazinylene, quinolinylene, phenanthrolinylene, thienylene, furylene, selenophenylene, thia Diazolylene, oxadiazolylene, selenadiazolylene or quinoxalylene, or a divalent group selected from the following structures;
Figure pat00075

R 31 to R 35 independently of one another are hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, tri Alicyclic, linked by (C3-C30) alkylene or (C3-C30) alkenylene, with or without fluoromethyl, phenyl, naphthyl, biphenyl, fluorenyl or phenanthryl A group ring and a monocyclic or polycyclic aromatic ring can be formed; L 21 and L 22 are each independently of each other phenylene, naphthylene, anthracenylene, fluorenylene, phenanthrylene, biphenylene, triphenylene, fluoranthrenylene, chrysenylene, pyrenylene, peryleneylene , Pyridinylene, furylene, thiophenylene, selenophenylene, pyridinylene, pyrazinylene, pyridazinylene, quinolinylene or quinoxalinylene; R 2 , R 3 , R 5 , R 6 , R 8 and R 9 are independently of each other hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl , Hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyri Dill, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; R 41 to R 44 independently of one another are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, indenyl, fluorenyl, benzofluorenyl, spirobiflu Orenyl, anthracenyl, pyrenyl, phenanthryl, triphenylenyl, fluoranthenyl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, benzofuranyl, benzothiophene 1, benzothiazolyl, benzooxazolyl, triazinyl or pyrimidyl or
Figure pat00076
ego; R 1 , R 4 , R 7 and R 10 are independently of each other hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl , Nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophene 1, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; L 11 , L 12 , L 21 , L 22 , R 1 to R 10 and R 41 to R 44 are deuterium, (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkoxy, cyano , One selected from (C1-C30) alkylsilyl, (C6-C30) arylsilyl, halo (C1-C30) alkyl, (C3-C30) heteroaryl, (C3-C30) cycloalkyl, nitro and hydroxy An organic light emitting compound which can be further substituted with the above substituents. 제 3항에 있어서,
상기
Figure pat00077
및
Figure pat00078
는 서로 독립적으로 하기 구조에서 선택되는 것을 특징으로 하는 유기 발광 화합물.
Figure pat00079

[R31 내지 R35는 서로 독립적으로 서로 독립적으로 (C1-C60)알킬 또는 (C6-C60)아릴이거나, 인접한 치환체와 융합고리를 포함하거나 포함하지 않는 (C3-C30)알킬렌 또는 (C3-C30)알케닐렌으로 연결되어 지환족 고리 및 단일환 또는 다환의 방향족 고리를 형성할 수 있다.]The method of claim 3, wherein
remind
Figure pat00077
And
Figure pat00078
Are independently selected from the following structures:
Figure pat00079

[R 31 to R 35 are independently of each other (C 1 -C 60) alkyl or (C 6 -C 60) aryl, or (C 3 -C 30) alkylene or (C 3-with or without fused ring with adjacent substituents. C30) may be linked to alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.] 제 1항 내지 제 4항에 따른 유기발광화합물을 포함하는 것을 특징으로 하는 유기발광소자.An organic light emitting device comprising the organic light emitting compound according to claim 1. 제 5항에 있어서,
상기 유기 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층으로 이루어져 있으며, 상기 유기물층은 상기 유기 발광 화합물 하나 이상과 하기 화학식 4 또는 화학식 5의 화합물에서 선택되는 호스트 하나 이상을 포함하는 것을 특징으로 하는 유기 발광 소자.
[화학식 4]
(Ar101)a-L101-(Ar102)b
[화학식 5]
(Ar103)c-L102-(Ar104)d
[상기 화학식 4 및 화학식 5에서,
L101는 (C6-C60)아릴렌 또는 (C4-C60)헤테로아릴렌이고;
L102는 안트라세닐렌이며;
Ar101 내지 Ar104은 서로 독립적으로 수소 또는 중수소이거나, (C1-C60)알킬, (C1-C60)알콕시, 할로겐, (C4-C60)헤테로아릴, (C5-C60)시클로알킬 또는 (C6-C60)아릴로부터 선택되고, 상기 Ar101 내지 Ar104의 시클로알킬, 아릴 또는 헤테로아릴은 할로겐이 치환되거나 치환되지 않은 (C1-C60)알킬, (C1-C60)알콕시, (C3-C60)시클로알킬, 할로겐, 시아노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로 이루어진 군으로부터 선택된 하나 이상이 치환되거나 치환되지 않은 (C6-C60)아릴 또는 (C4-C60)헤테로아릴, 할로겐이 치환되거나 치환되지 않은 (C1-C60)알킬, (C1-C60)알콕시, (C3-C60)시클로알킬, 할로겐, 시아노, 트리(C1-C60)알킬실릴, 디(C1-C60)알킬(C6-C60)아릴실릴 또는 트리(C6-C60)아릴실릴로 이루어지는 군에서 선택되는 하나 이상의 치환기가 더 치환될 수 있고;
a, b, c 및 d는 독립적으로 0 내지 4의 정수이다.]6. The method of claim 5,
The organic light emitting diode includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound and at least one host selected from a compound of Formula 4 or Formula 5 below. An organic light emitting element.
[Chemical Formula 4]
(Ar 101 ) a -L 101- (Ar 102 ) b
[Chemical Formula 5]
(Ar 103 ) c -L 102- (Ar 104 ) d
[In Formula 4 and Formula 5,
L 101 is (C6-C60) arylene or (C4-C60) heteroarylene;
L 102 is anthracenylene;
Ar 101 to Ar 104 are independently of each other hydrogen or deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) And cycloalkyl, aryl or heteroaryl of Ar 101 to Ar 104 are (C 1 -C 60) alkyl, (C 1 -C 60) alkoxy, (C 3 -C 60) cycloalkyl, with or without halogen; One or more selected from the group consisting of halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl is unsubstituted or substituted (C6-C60) aryl or (C4-C60) heteroaryl, substituted or unsubstituted halogen, (C1-C60) alkyl, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri One or more substituents selected from the group consisting of (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl or tri (C6-C60) arylsilyl may be further substituted And;
a, b, c and d are independently integers from 0 to 4. 제 6항에 있어서,
상기 유기물층에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 아민계 화합물을 더 포함하는 것을 특징으로 하는 유기 전계 발광 소자. The method of claim 6,
An organic electroluminescent device further comprising at least one amine compound selected from the group consisting of an arylamine compound or a styrylarylamine compound in the organic layer. 제 6항에 있어서,
상기 유기물층에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속을 더 포함하는 것을 특징으로 하는 유기 전계 발광 소자. The method of claim 6,
An organic electroluminescent device further comprising at least one metal selected from the group consisting of Group 1, Group 2, 4, 5 cycle transition metals, lanthanum series metals and organic metals of d-transition elements in the organic layer. 제 6항에 있어서,
상기 유기물층은 발광층 및 전하생성층을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.The method of claim 6,
The organic material layer is an organic electroluminescent device comprising a light emitting layer and a charge generating layer. 제 6항에 있어서,
상기 유기물층에 청색, 적색 또는 녹색 발광을 하는 유기발광층 하나 이상을 더 포함하여 백색 발광을 하는 것을 특징으로 하는 유기 전계 발광 소자.The method of claim 6,
The organic light emitting device of claim 1, further comprising at least one organic light emitting layer for emitting blue, red or green light to the organic material layer.
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