KR20140033968A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Organic light-emitting compound and organic electroluminescent device using the same Download PDF

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KR20140033968A
KR20140033968A KR1020120100607A KR20120100607A KR20140033968A KR 20140033968 A KR20140033968 A KR 20140033968A KR 1020120100607 A KR1020120100607 A KR 1020120100607A KR 20120100607 A KR20120100607 A KR 20120100607A KR 20140033968 A KR20140033968 A KR 20140033968A
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substituted
unsubstituted
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organic
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KR1020120100607A
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KR101488564B1 (en
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최태진
연규만
김동연
김충한
송보경
김지이
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주식회사 두산
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Priority to PCT/KR2013/001031 priority patent/WO2014042322A1/en
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Abstract

The present invention relates to a newly structured organic light emitting compound and an organic electroluminescent diode using the same and, more specifically, to an organic electroluminescent diode, including: a newly structured light emitting compound which is excellent in luminous capacity, positive hole transporting capacity, and electron transporting capacity; and one of the above compounds into an organic compound layer, so as to improve the luminance efficiency, driving voltage, and lifespan. The present invention can be effectively applied to a full-color display panel.

Description

유기발광 화합물 및 이를 이용한 유기 전계 발광 소자 {ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME} TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the same. BACKGROUND ART [0002]

본 발명은 신규의 유기발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 발광능, 정공 수송능, 전자 수송능 등이 우수한 신규의 유기발광 화합물, 및 상기 화합물을 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.
The present invention relates to a novel organic luminescent compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel organic luminescent compound having excellent light emitting ability, hole transporting ability and electron transporting ability, And the organic electroluminescent device is improved in characteristics such as luminous efficiency, driving voltage and lifetime.

유기 전계 발광 소자(organic electroluminescent device) (이하, 유기 EL 소자라 함)는 통상 양극과 음극 및 이들 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 EL 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공 주입층(HIL), 정공 수송층(HTL), 발광층(EML), 전자 수송층(ETL), 전자 주입층(EIL) 등을 포함할 수 있다. An organic electroluminescent device (hereinafter referred to as an organic EL device) generally has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic EL device, for example, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL) ), An electron injection layer (EIL), and the like.

이러한 유기 EL 소자의 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층으로 주입되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다.When a voltage is applied between the two electrodes of the organic EL device, holes are injected into the anode, electrons are injected into the organic layer, and excitons are formed when injected holes and electrons meet. When falling, the light comes out.

유기 EL 소자의 발광층 형성재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통해 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도펀트를 발광층에 소량 혼합하면, 호스트에서 발생한 엑시톤이 도펀트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도펀트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다. The light emitting layer forming material of the organic EL device can be classified into blue, green and red light emitting materials depending on the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. In addition, in order to increase luminous efficiency through increasing color purity and energy transfer, a host / dopant system may be used as the light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with a light emitting layer in a small amount, the excitons generated in the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

일반적으로 인광 호스트 재료로는 CBP(4,4-dicarbazolybiphenyl) 등의 카바졸계 화합물 등이 사용되며, 인광 도판트 재료로는 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물이 널리 사용되고 있다. 그러나 현재 사용되는 인광 호스트 재료인 CBP의 경우 유리전이온도(Tg)가 110℃ 정도로 낮으며, 소자 내의 결정화가 쉽게 일어나 유기 EL 소자의 수명이 150 시간 정도로 매우 짧은 문제점이 있다.
In general, carbazole compounds such as CBP (4,4-dicarbazolybiphenyl) are used as the phosphorescent host material, and metal complex compounds containing heavy atoms such as Ir and Pt are widely used as the phosphorescent dopant material. It is used. However, CBP, which is a phosphorescent host material currently used, has a low glass transition temperature (Tg) of about 110 ° C. and easily crystallizes in the device, resulting in a very short lifetime of the organic EL device to about 150 hours.

본 발명은 전술한 목적을 해결하기 위해서 안출된 것으로서, 발광효율, 구동전압, 열적 안정성, 수명 등의 특성을 향상시킬 수 있는 유기발광 화합물 및 이를 이용한 유기 EL 소자를 제공하는 것을 목적으로 한다.
The present invention has been made to solve the above object, and an object of the present invention is to provide an organic light emitting compound and an organic EL device using the same that can improve the characteristics such as luminous efficiency, driving voltage, thermal stability, life.

상기 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).

Figure pat00001
Figure pat00001

상기 식에서,Where

R1 및 R2는 서로 같거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기, -P(=O)RaRb, 치환 또는 비치환된 C3~C40의 시클로알킬기 및 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기로 이루어진 군에서 선택되거나, 또는 이들이 인접하는 기와 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리 또는 축합 헤테로방향족 고리를 형성하는 기이며, R 1 and R 2 are the same or different and each independently represents hydrogen, deuterium, halogen, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 ~ C 40 of the alkynyl group, a substituted or unsubstituted C 6 ~ C 40 aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, substituted or non-substituted of unsubstituted C 6 ~ C for 40 aryloxy group, a substituted or unsubstituted C 1 ~ alkyloxy group of C 40, -P (= O) R a R b, a substituted or unsubstituted C 3 ~ C 40 cycloalkyl group and a substituted or Or a heterocycloalkyl group having 3 to 40 unsubstituted nucleus atoms or a group which forms a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with the adjacent groups,

여기서 Ra 및 Rb는 서로 같거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기 및 치환 또는 비치환된 C3~C40의 시클로알킬기로 이루어진 군에서 선택되거나, 또는 이들이 인접하는 기와 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리 또는 축합 헤테로방향족 고리를 형성하는 기이다.Wherein R a and R b are the same or different and each independently represents a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 ~ C 40 alkenyl group, a substituted or unsubstituted C 2 ~ C 40 of the alkynyl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C 6 ~ C 40 aryl group A substituted or unsubstituted C 1 to C 40 alkyloxy group and a substituted or unsubstituted C 3 to C 40 cycloalkyl group, or a group selected from the group consisting of a condensed aliphatic ring and a condensed aromatic ring , A fused heteroaliphatic ring or a group that forms a fused heteroaromatic ring.

본 발명은 또한 (i) 양극, (ⅱ) 음극, 및 (ⅲ) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 EL 소자로서, 상기 유기물층 중 적어도 하나는 본 발명의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 EL 소자를 제공한다.
The present invention also provides an organic EL device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the organic layers comprises An organic EL device characterized by comprising a compound represented by the formula (1).

본 발명의 화학식 1로 표시되는 화합물은 우수한 발광능, 전자 수송능 및 정공 수송능을 가지고 있다. 따라서, 이를 포함하는 유기 EL 소자는 발광성능, 구동전압, 수명 등의 특성이 크게 향상될 수 있으므로, 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.
The compound represented by the formula (1) of the present invention has excellent luminous ability, electron transport ability and hole transport ability. Therefore, the organic EL device including the same may greatly improve characteristics such as light emission performance, driving voltage, and lifetime, and thus may be effectively applied to a full color display panel.

이하, 본 발명에 대하여 상세히 설명한다. Hereinafter, the present invention will be described in detail.

<신규 화합물><Novel compound>

본 발명에 따른 신규 유기발광 화합물은 다이하이드로페란스렌계의 모핵에 다양한 치환체, 특히 N-함유 헤테로환, 방향족 고리 등이 연결된 상기 화학식 1로 표시되는 구조를 가진다. 이러한 구조를 통해 충분히 높은 삼중항 에너지 레벨을 달성하여 인광특성을 개선함과 동시에 전자(electron) 및/또는 정공(hole) 수송 능력, 발광효율, 구동전압, 수명 특성 등에서 개선된 효능을 달성할 수 있다.The novel organic electroluminescent compound according to the present invention has a structure represented by the above formula (1) in which various substituents, particularly N-containing heterocyclic rings, aromatic rings, and the like, are connected to the parent moiety of the dihydroperoylene system. Through such a structure, it is possible to attain a sufficiently high triplet energy level to improve the phosphorescence characteristic and at the same time to achieve an improved effect in electron and / or hole transporting ability, luminous efficiency, driving voltage, have.

본 발명에 따라 화학식 1로 표시되는 화합물에서, 상기 R1 및 R2 는 서로 같거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, -P(=O)RaRb, C3~C40의 시클로알킬기 및 핵원자수 3 내지 40의 헤테로시클로알킬기로 이루어진 군에서 선택되거나, 또는 이들이 인접하는 기와 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리 또는 축합 헤테로방향족 고리를 형성하는 기일 수 있다. According to the present invention, in the compound represented by the general formula (1), R 1 and R 2 are the same or different and each independently represents hydrogen, deuterium, halogen, C 1 to C 40 alkyl, C 2 to C 40 A C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group , -P (= O) R a R b , a C 3 -C 40 cycloalkyl group, and a heterocycloalkyl group having 3 to 40 nuclear atoms, or a group consisting of a condensed aliphatic ring and a condensed aromatic ring , A condensed heteroaliphatic ring, or a group that forms a fused heteroaromatic ring.

여기서 Ra및 Rb는 서로 같거나 또는 상이하며, 각각 독립적으로 C6~C40의 아릴기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기 및 C3~C40의 시클로알킬기로 이루어진 군에서 선택되거나, 또는 이들이 인접하는 기와 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리 또는 축합 헤테로방향족 고리를 형성하는 기이다.Wherein R a and R b are the same or different and each independently represents a C 6 to C 40 aryl group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkoxy A heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group, and a C 3 to C 40 cycloalkyl group, or a group selected from the group consisting of An adjacent group and a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring.

이때 상기 화학식 1에서, 전술한 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기 및 핵원자수 3 내지 40의 헤테로시클로알킬기는, 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환될 수 있다. 바람직하게는 C1~C3의 알킬기, C6~C8 아릴기, 핵원자수 5 내지 6의 헤테로아릴기로 구성된 군에서 선택되는 하나 이상의 치환기로 치환될 수 있다.In the formula 1, the above-mentioned C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 6 to C 40 aryl group, A heteroaryl group, a C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group, a C 3 to C 40 cycloalkyl group, and a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms are each independently substituted with deuterium, A halogen atom, a cyano group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms , A C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group, a C 6 to C 40 arylamine group, a C 6 to C 40 arylalkyl group, a C 3 to C 40 cycloalkyl group, a C A C 3 to C 40 heterocycloalkyl group, a C 1 to C 40 alkylsilyl group, and a C 6 to C 40 arylsilyl group. Preferably one or more substituents selected from the group consisting of a C 1 to C 3 alkyl group, a C 6 to C 8 aryl group, and a heteroaryl group having 5 to 6 nuclear atoms.

본 발명에 따른 화학식 1로 표시되는 화합물에서, 삼중항 에너지 레벨을 고려했을 때, R1 및 R2 는 서로 같거나 또는 상이하며, 각각 독립적으로 C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기이거나, 또는 이들이 인접하는 기와 형성하는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리 또는 축합 헤테로방향족 고리일 수 있다. In the compound represented by the formula (1) according to the present invention, when considering the triplet energy level, R 1 and R 2 are the same or different and each independently represents a C 6 to C 40 aryl group, To about 40 heteroaryl groups, or condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, or condensed heteroaromatic rings forming a group adjacent thereto.

여기서, 상기 C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환될 수 있다. The C 6 -C 40 aryl group and the heteroaryl group having 5 to 40 nucleus atoms are each independently selected from the group consisting of deuterium, halogen, cyano, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of, C 6 ~ C 40 aryl amine group, C 6 ~ C 40 aryl group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 of the heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, and a C 6 ~ of with one or more substituents selected from aryl silyl group consisting of C 40 it can be replaced.

일례로, 상기 C6~C40의 아릴기 또는 핵원자수 5 내지 40의 헤테로아릴기는 페닐, 나프틸, 인덴, 안트라센, 페난트렌, 파이렌, 트리페닐렌, 피리딘, 피리미딘, 피라진, 트리아진, 퀴놀린, 이소퀴놀린, 퀴녹살린, 플루오렌, 카바졸, 디벤조싸이오펜, 디벤조퓨란, 아크리딘, 인돌, 벤조퓨란, 벤조싸이오펜, 벤즈이미다졸, 벤조싸이아졸, 퓨린, 페난트롤린일 수 있다. For example, the C 6 -C 40 aryl group or the heteroaryl group having 5 to 40 nuclear atoms may be substituted with at least one group selected from phenyl, naphthyl, indene, anthracene, phenanthrene, pyrene, triphenylene, pyridine, pyrimidine, pyrazine, And examples thereof include azine, quinoline, isoquinoline, quinoxaline, fluorene, carbazole, dibenzothiophene, dibenzofuran, acridine, indole, benzofuran, benzothiophene, benzimidazole, benzothiazole, It can be Lin.

본 발명에 따라 상기 화학식 1의 화합물은 하기 화학식 2 또는 화학식 3으로 표시되는 화합물 중 어느 하나로 보다 구체화될 수 있다.According to the present invention, the compound of formula (1) may be further represented by any one of the compounds represented by the following formulas (2) and (3).

Figure pat00002
Figure pat00002

Figure pat00003
Figure pat00003

상기 식에서, Where

X1 내지 X10는 서로 같거나 또는 상이하며, 각각 독립적으로 C 또는 N이며,X 1 to X 10 are the same or different and are each independently C or N,

R3 내지 R16는 서로 같거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, C1~C10의 알킬기, C2~C10의 알케닐기, C2~C10의 알키닐기, C6~C8의 아릴기, 핵원자수 5 내지 8의 헤테로아릴기, C3~C10의 시클로알킬기 및 핵원자수 3 내지 10의 헤테로시클로알킬기로 이루어진 군에서 선택된다. R 3 to R 16 are to each other the same or different and each independently represent hydrogen, deuterium, halogen, C 1 ~ C 10 alkyl group, C 2 ~ alkynyl, C 6 of the C 10 alkenyl group, C 2 ~ C 10 of the ~ C 8 of the aryl group, an aryl nuclear atoms of 5 to 8, a heterocyclic group, is selected from the group consisting of a heterocycloalkyl group of C 3 ~ C 10 cycloalkyl group and the number of nuclear atoms of 3 to 10.

여기서, 상기 C1~C10의 알킬기, C2~C10의 알케닐기, C2~C10의 알키닐기, C6~C8의 아릴기, 핵원자수 5 내지 8의 헤테로아릴기, C3~C10의 시클로알킬기 및 핵원자수 3 내지 10의 헤테로시클로알킬기는, 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환될 수 있다Here, the C 1 -C 10 alkyl group, the C 2 -C 10 alkenyl group, the C 2 -C 10 alkynyl group, the C 6 -C 8 aryl group, the heteroaryl group having 5 to 8 nuclear atoms, the C 3 or heterocycloalkyl group of C 10 cycloalkyl group and the number of nuclear atoms of 3 to 10 are each independently a heavy hydrogen, a halogen, a cyano group, an alkenyl group of C 1 ~ C 40 alkyl group, C 2 ~ C 40 of, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of, C 6 ~ C 40 arylamine group, C 6 ~ C 40 aryl group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, and C 6 ~ C 40 of &Lt; / RTI &gt; arylsilyl &lt; RTI ID = 0.0 &gt;

본 발명에서 사용된 "비치환된 알킬"은 탄소수 1 내지 40(10)의 직쇄 또는 측쇄의 포화 탄화수소이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 포함한다. As used herein, “unsubstituted alkyl” is a straight or branched chain saturated hydrocarbon of 1 to 40 (10) carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, Hexyl and the like.

"비치환된 아릴"은 단독 고리 혹은 2 이상의 고리가 조합된, 탄소수 6 내지 40(8)의 방향족 부위를 의미한다. 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태로 부착될 수 있다. "Unsubstituted aryl" means an aromatic moiety having 6 to 40 (8) carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached to each other in a pendant or condensed form.

"비치환된 헤테로아릴"은 핵원자수 5 내지 40(8)의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 부위를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S와 같은 헤테로원자로 치환된다. 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태로 부착될 수 있고, 나아가 지방족 고리 또는 방향족 고리와의 축합된 형태도 포함하는 것으로 해석한다. "Unsubstituted heteroaryl" means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 40 (8) nucleoatoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, Substituted by heteroatoms such as O and S. Two or more rings may be attached in a pendant or condensed form to each other and further include a condensed form with an aliphatic ring or an aromatic ring.

"축합 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다."Condensation ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

이상에서 설명한 본 발명의 화학식 1로 표시되는 화합물은 하기 예시된 화학식들로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compound represented by the formula (1) of the present invention described above may be further embodied by the formulas illustrated below. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

Figure pat00004
Figure pat00004

Figure pat00005
Figure pat00005

Figure pat00006
Figure pat00006

Figure pat00007

Figure pat00007

본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다. 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다.
The compound of formula 1 of the present invention may be synthesized according to a general synthetic method. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

<유기 전계 발광 소자>&Lt; Organic electroluminescent device &

한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다. On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.

보다 구체적으로, 본 발명에 따른 유기 전계 발광소자는 (i) 양극(anode); (ⅱ) 음극(cathode); 및 (ⅲ) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 한다. 이때, 상기 화학식 1로 표시되는 화합물은 1종 또는 2종 이상이 포함될 수 있다.More specifically, the organic electroluminescent device according to the present invention includes (i) an anode; (Ii) a cathode; And (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by the formula (1). In this case, the compound represented by Formula 1 may include one kind or two or more kinds.

여기서, 본 발명의 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층, 정공주입층, 정공수송층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있으며, 바람직하게는 발광층, 정공수송층 및/또는 전자수송층일 수 있다.Here, the organic material layer containing the compound represented by the formula (1) of the present invention may be any one or more of a light emitting layer, a hole injecting layer, a hole transporting layer, an electron transporting layer and an electron injecting layer, Lt; / RTI &gt;

본 발명에 따른 유기 전계 발광 소자의 발광층은 호스트 재료를 함유할 수 있는데, 이때 호스트 재료로 상기 화학식 1로 표시되는 화합물 중 어느 하나를 사용할 수 있다. 이와 같이 발광층이 상기 화학식 1로 표시되는 화합물 중 어느 하나를 함유할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 우수한 유기 전계 발광 소자를 제공할 수 있다. 상기 화학식 1로 표시되는 화합물은 청색, 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 발광 소자에 포함될 수 있다. 또한 도펀트 재료로 이용될 수 있다. The light emitting layer of the organic electroluminescent device according to the present invention may contain a host material, wherein any one of the compounds represented by Formula 1 may be used as the host material. As such, when the light emitting layer contains any one of the compounds represented by Chemical Formula 1, organic electroluminescence having excellent efficiency (light emitting efficiency and power efficiency), lifetime, luminance, driving voltage, etc., because the bonding force between holes and electrons in the light emitting layer is increased. An element can be provided. The compound represented by Formula 1 may be included in an organic light emitting device as a blue, green, and / or red phosphorescent host, a fluorescent host, or a dopant material. It can also be used as a dopant material.

본 발명의 유기 EL 소자 구조는 특별히 한정되지 않으나, 전극간에 유기물층을 1층 또는 2층 이상 적층한 구조일 수 있다. 이의 비제한적인 예를 들면 (i) 양극, 발광층, 음극; (ⅱ) 양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층, 음극; 또는 (ⅲ) 양극, 정공주입층, 정공수송층, 발광층, 음극 등의 구조를 들 수 있다.The structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which one or more organic layers are laminated between electrodes. Non-limiting examples thereof include (i) an anode, a light emitting layer, a cathode; (Ii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a cathode; Or (iii) structures such as an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode.

또한, 본 발명에 따른 유기 EL 소자는 전술한 바와 같이 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입될 수 있다. In addition, the organic EL device according to the present invention may have an insulating layer or an adhesive layer inserted into the interface between the electrode and the organic layer as well as the structure in which the anode, one or more organic layers and the cathode are sequentially stacked, as described above.

본 발명에 따른 유기 EL 소자에 있어서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 진공증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에만 한정되지 않는다. In the organic EL device according to the present invention, the organic material layer including the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

본 발명에 따른 유기 EL 소자는 유기물층 중 1층 이상을 본 발명의 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 유기물층 및 전극을 형성함으로써 제조될 수 있다. The organic EL device according to the present invention forms an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Formula 1 of the present invention. It can be manufactured by.

예컨대, 기판으로는 실리콘 웨이퍼, 석영 또는 유리판, 금속판, 플라스틱 필름이나 시트 등이 사용될 수 있다. For example, a silicon wafer, quartz or glass plate, a metal plate, a plastic film or a sheet can be used as the substrate.

양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블랙 등이 있으나, 이들에만 한정되는 것은 아니다. Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.

음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.

또한, 정공 주입층, 정공 수송층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당업계에 알려진 통상의 물질이 사용될 수 있다. The hole injecting layer, the hole transporting layer and the electron transporting layer are not particularly limited, and ordinary materials known in the art can be used.

이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.
Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[합성예 1] Cpd 1 (2,7-di(9H-carbazol-9-yl)-9,10-dihydrophenanthrene)의 합성Synthesis Example 1 Synthesis of Cpd 1 (2,7-di (9H-carbazol-9-yl) -9,10-dihydrophenanthrene)

Figure pat00008
Figure pat00008

2,7-dibromo-9,10-dihydrophenanthrene(10g, 29.58mmol)과 carbazole (12.4g, 73.95mmol)을 톨루엔 300 ㎖에 녹인 다음 Pd2(dba)3 (1.4g, 1.48mmol)을 질소하에 투입하였다. 이후, NaOBu-t (17.0g, 176.88mmol)을 넣고, (t-Bu)3P (1.48 ㎖, 1.48mmol)을 상기 반응액에 투입한 다음 혼합물을 5시간 동안 환류 교반하였다. 2,2-dibromo-9,10-dihydrophenanthrene (10 g, 29.58 mmol) and carbazole (12.4 g, 73.95 mmol) were dissolved in 300 ml of toluene and then Pd 2 (dba) 3 (1.4 g, 1.48 mmol) Respectively. Then, NaOBu-t (17.0 g, 176.88 mmol) was added, and (t-Bu) 3 P (1.48 mL, 1.48 mmol) was added to the reaction solution and the mixture was refluxed with stirring for 5 hours.

TLC로 반응이 종결되는 것을 확인한 후 상온으로 식혔다. 반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 화합물 Cpd1(21.5g, 수율 70%)을 얻었다. HRMS [M]+:510.209
After confirming that the reaction was terminated by TLC, the mixture was cooled to room temperature. After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain Cpd 1 (21.5 g, yield 70%). HRMS [M] &lt; + & gt ; : 510.209

[합성예 2] Cpd 4 (2,7-bis(3,6-difluoro-9H-carbazol-9-yl)-9,10-dihydrophenanthrene)의 합성Synthesis Example 2 Synthesis of Cpd 4 (2,7-bis (3,6-difluoro-9H-carbazol-9-yl) -9,10-dihydrophenanthrene)

Carbazole 대신 3,6-difluoro-9H-carbazole를 사용하는 것을 제외하고는, 상기 합성예 1과 동일한 과정을 수행하여 표제 화합물 Cpd4 (수율 68%)을 얻었다. HRMS [M]+:582.171
The title compound Cpd4 (yield 68%) was obtained by following the same procedure as in Synthesis Example 1, except that 3,6-difluoro-9H-carbazole was used instead of Carbazole. HRMS [M] &lt; + & gt ; : 582.171

[합성예 3] Cpd 7 (2,7-bis(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthrene)의 합성Synthesis Example 3 Synthesis of Cpd 7 (2,7-bis (dibenzo [b, d] thiophen-4-yl) -9,10-dihydrophenanthrene

Figure pat00009
Figure pat00009

2,7-dibromo-9,10-dihydrophenanthrene(10g, 29.58mmol), dibenzothiophenyl boronic acid (16.9g, 73.95mmol) 및 Pd(PPh3)4 (3.4g, 3.0mmol)을 플라스크에 넣고 2N Na2CO3 포화 수용액 177.5㎖와 Toluene 240 ㎖, EtOH 60 ㎖를 넣어 녹인 후 13시간 동안 가열 교반하였다. Dibenzothiophenyl boronic acid (16.9 g, 73.95 mmol) and Pd (PPh 3 ) 4 (3.4 g, 3.0 mmol) were placed in a flask and 2N Na 2 CO 3 saturated aqueous solution, 240 ml of toluene and 60 ml of EtOH, and the mixture was heated and stirred for 13 hours.

반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 화합물 Cpd7 (12.9g, 수율 80%)을 얻었다. HRMS [M]+:544.131
After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain Cpd 7 (12.9 g, yield 80%). HRMS [M] &lt; + & gt ; : 544.131

[[ 합성예Synthetic example 4]  4] CpdCpd 8 (9-(7-( 8- (9- (7- ( dibenzodibenzo [b,d]thiophen-4-[b, d] thiophen-4- ylyl )-9,10-dihydrophenanthren-2-yl)-9H-carbazole)의 합성) -9,10-dihydrophenanthren-2-yl) -9H-carbazole

Figure pat00010
Figure pat00010

<단계 1> 2-<Step 1> 2- bromobromo -7-(-7- ( dibenzodibenzo [b,d]thiophen-4-[b, d] thiophen-4- ylyl )-9,10-) -9,10- dihydrophenanthrenedihydrophenanthrene 의 합성Synthesis of

2,7-dibromo-9,10-dihydrophenanthrene(10g, 29.58mmol), dibenzothiophenyl boronic acid (6.7g, 29.58mmol) 및 Pd(PPh3)4 (1.7g, 1.47mmol)을 플라스크에 넣고 2N Na2CO3 포화 수용액 88.7㎖와 Toluene 240 ㎖, EtOH 60 ㎖를 넣어 녹인 후 13시간 동안 가열 교반하였다. 2,7-dibromo-9,10-dihydrophenanthrene ( 10g, 29.58mmol), dibenzothiophenyl boronic acid (6.7g, 29.58mmol) and Pd (PPh 3) 4 into a (1.7g, 1.47mmol) the flask 2N Na 2 CO 3 saturated aqueous solution, 240 ml of toluene and 60 ml of EtOH, and the mixture was heated and stirred for 13 hours.

반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 표제 화합물(7.8g, 수율 60%)을 얻었다. HRMS [M]+:440.023After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound (7.8 g, yield 60%). HRMS [M] &lt; + & gt ; : 440.023

<단계 2> 9-(7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthren-2-yl)-9H-carbazole 의 합성Synthesis of 9- (7- (dibenzo [b, d] thiophen-4-yl) -9,10-dihydrophenanthren-2-yl) -9H-carbazole

2-bromo-7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthrene (7.8g, 17.67mmol), carbazole (3.5g, 20.93mmol)을 톨루엔 170 ㎖에 녹인 다음 Pd2(dba)3 (0.83g, 0.88mmol)을 질소하에 투입하였다. 이후, NaOBu-t (5.0g, 53.01mmol)을 넣고, (t-Bu)3P (0.9 ㎖, 0.9mmol)을 상기 반응액에 투입한 다음 혼합물을 5시간 동안 환류 교반하였다. 4-yl) -9,10-dihydrophenanthrene (7.8 g, 17.67 mmol) and carbazole (3.5 g, 20.93 mmol) were dissolved in 170 ml of toluene, and then Pd 2 (dba) 3 (0.83 g, 0.88 mmol) was added under nitrogen. Then, NaOBu-t (5.0 g, 53.01 mmol) was added, and (t-Bu) 3 P (0.9 ml, 0.9 mmol) was added to the reaction solution and the mixture was refluxed with stirring for 5 hours.

TLC로 반응이 종결되는 것을 확인한 후 상온으로 식혔다. 반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 화합물 Cpd 8 (7.4g, 수율 80%)을 얻었다. HRMS [M]+:527.120
After confirming that the reaction was terminated by TLC, the mixture was cooled to room temperature. After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain a compound Cpd 8 (7.4 g, yield 80%). HRMS [M] &lt; + & gt ; : 527.120

[합성예 5] Cpd 12 (9-(7-(4,6-diphenyl-1,3,5-triazin-2-yl)-9,10-dihydrophenanthren2-yl)-9H-carbazole)의 합성Synthesis Example 5 Synthesis of Cpd 12 (9- (7- (4,6-diphenyl-1,3,5-triazin-2-yl) -9,10-dihydrophenanthren-yl) -9H-carbazole

Figure pat00011
Figure pat00011

<단계 1> 9-(7-bromo-9,10-dihydrophenanthren-2-yl)-9H-carbazole의 합성<Step 1> Synthesis of 9- (7-bromo-9,10-dihydrophenanthren-2-yl) -9H-carbazole

2,7-dibromo-9,10-dihydrophenanthrene(10g, 29.58mmol), carbazole (4.94g, 29.58mmol)을 톨루엔 300 ㎖에 녹인 다음 Pd(OAc)2 (0.33g, 1.48mmol)을 질소하에 투입하였다. 이후, Cs2CO3 (19.3g, 59.23mmol)을 넣고, BINAP (0.92g, 1.48mmol)을 상기 반응액에 투입한 다음 혼합물을 5시간 동안 환류 교반하였다.2,7-dibromo-9,10-dihydrophenanthrene (10 g, 29.58 mmol) and carbazole (4.94 g, 29.58 mmol) were dissolved in 300 ml of toluene and then Pd (OAc) 2 (0.33 g, 1.48 mmol) . Then, Cs 2 CO 3 (19.3 g, 59.23 mmol) was added, BINAP (0.92 g, 1.48 mmol) was added to the reaction solution, and the mixture was refluxed with stirring for 5 hours.

TLC로 반응이 종결되는 것을 확인한 후 상온으로 식혔다. 반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 화합물 Cpd8(7.5g, 수율 60%)을 얻었다. HRMS [M]+:423.062After confirming that the reaction was terminated by TLC, the mixture was cooled to room temperature. After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain a compound Cpd 8 (7.5 g, yield 60%). HRMS [M] &lt; + & gt ; : 423.062

<단계 2> 9-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydrophenanthren-2-yl)-9H-carbazole의 합성Synthesis of 9- (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9,10-dihydrophenanthren-2-yl) -9H-carbazole

9-(7-bromo-9,10-dihydrophenanthren-2-yl)-9H-carbazole(7.5g, 17.67mmol), Bis(pinacolato)diboron (5.4g, 21.26mmol), KOAc(5.2g, 52.98mmol) 및 Pd(dppf)Cl2(0.72g, 0.88mmol)을 톨루엔 200 ㎖에 녹인 다음 혼합물을 5시간 동안 환류 교반하였다. (7.5g, 17.67mmol), Bis (pinacolato) diboron (5.4g, 21.26mmol), KOAc (5.2g, 52.98mmol) and 9- (7bromo- And Pd (dppf) Cl 2 (0.72 g, 0.88 mmol) were dissolved in 200 ml of toluene, and the mixture was refluxed with stirring for 5 hours.

TLC로 반응이 종결되는 것을 확인한 후 상온으로 식혔다. 반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 화합물 (7.0g, 수율 85%)을 얻었다. HRMS [M]+:471.237After confirming that the reaction was terminated by TLC, the mixture was cooled to room temperature. After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain a compound (7.0 g, yield 85%). HRMS [M] &lt; + & gt ; : 471.237

<단계 3> 9-(7-(4,6-diphenyl-1,3,5-triazin-2-yl)-9,10-dihydrophenanthren-2-yl)-9H-carbazole의 합성Synthesis of 9- (7- (4,6-diphenyl-1,3,5-triazin-2-yl) -9,10-dihydrophenanthren-2-yl) -9H-carbazole

9-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydrophenanthren-2-yl)-9H-carbazole (7.0g, 14.84mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.8g, 17.81mmol) 및 Pd(PPh3)4 (860mg, 0.74mmol)을 플라스크에 넣고 2N Na2CO3 포화 수용액 52.8㎖와 Toluene 160 ㎖, EtOH 40 ㎖를 넣어 녹인 후 13시간 동안 가열 교반하였다. 9- (7- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9,10-dihydrophenanthren- 2-yl) -9H-carbazole (7.0 g, 14.84 mmol) , 2-chloro-4,6-diphenyl -1,3,5-triazine (4.8g, 17.81mmol) and Pd (PPh 3) 4 (860mg , 0.74mmol) were placed in the flask and 2N Na 2 CO 3 saturated aqueous solution 52.8 160 ml of toluene, and 40 ml of EtOH were added to the solution, followed by heating and stirring for 13 hours.

반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 화합물 Cpd12 (7.3g, 수율 85%)을 얻었다. HRMS [M]+:576.231
After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain a compound Cpd 12 (7.3 g, yield 85%). HRMS [M] &lt; + & gt ; : 576.231

[합성예 6] Cpd 11 (9-(7-(4,6-diphenylpyrimidin-2-yl)-9,10-dihydrophenanthren-2-yl)-9H-carbazole)의 합성Synthesis Example 6 Synthesis of Cpd 11 (9- (7- (4,6-diphenylpyrimidin-2-yl) -9,10-dihydrophenanthren-2-yl) -9H-carbazole

2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4,6-diphenylpyrimidine 를 사용하는 것을 제외하고는, 상기 합성예 5와 동일한 과정을 수행하여 표제 화합물 Cpd11 (수율 68%)을 얻었다. HRMS [M]+:575.236
The procedure of Synthesis Example 5 was repeated except that 2-chloro-4,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the title compound Cpd11 68%). HRMS [M] &lt; + & gt ; : 575.236

[합성예 7] Cpd 13 (9-(7-(4,6-diphenylpyrimidin-2-yl)-9,10-dihydrophenanthren-2-yl)-9H-carbazole)의 합성Synthesis Example 7 Synthesis of Cpd 13 (9- (7- (4,6-diphenylpyrimidin-2-yl) -9,10-dihydrophenanthren-2-yl) -9H-carbazole

2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-bromo-4,6-diphenylpyridine 를 사용하는 것을 제외하고는, 상기 합성예 5와 동일한 과정을 수행하여 표제 화합물 Cpd13 (수율 70%)을 얻었다. HRMS [M]+:574.240
The procedure of Synthetic Example 5 was repeated except that 2-bromo-4,6-diphenylpyridine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the title compound Cpd13 70%). HRMS [M] &lt; + & gt ; : 574.240

[합성예 8] Cpd 14 (9-(7-(4,6-diphenylpyrimidin-2-yl)-9,10-dihydrophenanthren-2-yl)-9H-carbazole)의 합성Synthesis Example 8 Synthesis of Cpd 14 (9- (7- (4,6-diphenylpyrimidin-2-yl) -9,10-dihydrophenanthren-2-yl) -9H-carbazole

2-chloro-4,6-diphenyl-1,3,5-triazine 대신 1-Bromo-3,5-diphenylbenzene 를 사용하는 것을 제외하고는, 상기 합성예 5와 동일한 과정을 수행하여 표제 화합물 Cpd14 (수율 75%)을 얻었다. HRMS [M]+:573.245
The procedure of Synthetic Example 5 was repeated except that 1-Bromo-3,5-diphenylbenzene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the title compound Cpd14 75%). HRMS [M] &lt; + & gt ; : 573.245

[합성예 9] Cpd 15 (2-(7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthren-2-yl)-4,6-diphenyl-1,3,5-triazine)의 합성Synthesis Example 9 Synthesis of Cpd 15 (2- (7- (dibenzo [b, d] thiophen-4-yl) -9,10-dihydrophenanthren- triazine)

Figure pat00012
Figure pat00012

<단계 1> 2-bromo-7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthrene의 합성Step 1 Synthesis of 2-bromo-7- (dibenzo [b, d] thiophen-4-yl) -9,10-dihydrophenanthrene

2,7-dibromo-9,10-dihydrophenanthrene(10g, 29.58mmol), dibenzothiophenyl boronic acid (6.7g, 29.58mmol) 및 Pd(PPh3)4 (1.7g, 1.47mmol)을 플라스크에 넣고 2N Na2CO3 포화 수용액 88.7㎖와 Toluene 240 ㎖, EtOH 60 ㎖를 넣어 녹인 후 13시간 동안 가열 교반하였다. 2,7-dibromo-9,10-dihydrophenanthrene ( 10g, 29.58mmol), dibenzothiophenyl boronic acid (6.7g, 29.58mmol) and Pd (PPh 3) 4 into a (1.7g, 1.47mmol) the flask 2N Na 2 CO 3 saturated aqueous solution, 240 ml of toluene and 60 ml of EtOH, and the mixture was heated and stirred for 13 hours.

반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 표제 화합물(7.8g, 수율 60%)을 얻었다. HRMS [M]+:440.023After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound (7.8 g, yield 60%). HRMS [M] &lt; + & gt ; : 440.023

<단계 2> 2-(7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane의 합성Step 2: Synthesis of 2- (7- (dibenzo [b, d] thiophen-4-yl) -9,10- dihydrophenanthren- 2-yl) -4,4,5,5-tetramethyl- Synthesis of dioxaborolane

2-bromo-7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthrene (7.8g, 17.67mmol), Bis(pinacolato)diboron (5.4g, 21.26mmol), KOAc(5.2g, 52.98mmol) 및 Pd(dppf)Cl2(0.72g, 0.88mmol)을 톨루엔 200 ㎖에 녹인 다음 혼합물을 5시간 동안 환류 교반하였다. (7.8g, 17.67mmol), Bis (pinacolato) diboron (5.4g, 21.26mmol), KOAc (5.2gmol) were added to a solution of 2-bromo-7- (dibenzo [b, d] thiophen- , 52.98 mmol) and Pd (dppf) Cl 2 (0.72 g, 0.88 mmol) were dissolved in 200 ml of toluene, and the mixture was refluxed with stirring for 5 hours.

TLC로 반응이 종결되는 것을 확인한 후 상온으로 식혔다. 반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 화합물 (8.3g, 수율 85%)을 얻었다. HRMS [M]+:471.237After confirming that the reaction was terminated by TLC, the mixture was cooled to room temperature. After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain a compound (8.3 g, yield 85%). HRMS [M] &lt; + & gt ; : 471.237

<단계 3> 2-(7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthren-2-yl)-4,6-diphenyl-1,3,5-triazine 의 합성Synthesis of 2- (7- (dibenzo [b, d] thiophen-4-yl) -9,10-dihydrophenanthren- 2- yl) -4,6-diphenyl-1,3,5-triazine

2-(7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.2g, 14.84mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.8g, 17.81mmol) 및 Pd(PPh3)4 (860mg, 0.74mmol)을 플라스크에 넣고 2N Na2CO3 포화 수용액 52.8㎖와 Toluene 160 ㎖, EtOH 40 ㎖를 넣어 녹인 후 13시간 동안 가열 교반하였다. 2- (7- (dibenzo [b, d] thiophen-4-yl) -9,10-dihydrophenanthren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4,8 g, 17.81 mmol) and Pd (PPh 3 ) 4 (860 mg, 0.74 mmol) were placed in a flask and 2N Na 2 CO 3 saturated aqueous solution, 160 ml of Toluene and 40 ml of EtOH, and the mixture was heated and stirred for 13 hours.

반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 화합물 Cpd15 (7.0g, 수율 80%)을 얻었다. HRMS [M]+:593.192
After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain a compound Cpd 15 (7.0 g, yield 80%). HRMS [M] &lt; + & gt ; : 593.192

[합성예 10] Cpd 16 (2-(7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthren-2-yl)-4,6-diphenylpyrimidine)의 합성Synthesis Example 10 Synthesis of Cpd 16 (2- (7- (dibenzo [b, d] thiophen-4-yl) -9,10-dihydrophenanthren-2-yl) -4,6-diphenylpyrimidine

2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-chloro-4,6-diphenylpyrimidine 를 사용하는 것을 제외하고는, 상기 합성예 5와 동일한 과정을 수행하여 표제 화합물 Cpd16 (수율 68%)을 얻었다. HRMS [M]+:592.197
The procedure of Synthetic Example 5 was repeated except that 2-chloro-4,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the title compound Cpd16 68%). HRMS [M] &lt; + & gt ; : 592.197

[합성예 11] Cpd 17 (2-(7-(dibenzo[b,d]thiophen-4-yl)-9,10-dihydrophenanthren-2-yl)-4,6-diphenylpyridine)의 합성Synthesis Example 11 Synthesis of Cpd 17 (2- (7- (dibenzo [b, d] thiophen-4-yl) -9,10-dihydrophenanthren-2-yl) -4,6-diphenylpyridine

2-chloro-4,6-diphenyl-1,3,5-triazine 대신 2-bromo-4,6-diphenylpyridine 를 사용하는 것을 제외하고는, 상기 합성예 5와 동일한 과정을 수행하여 표제 화합물 Cpd17 (수율 70%)을 얻었다. HRMS [M]+:591.202
The procedure of Synthesis Example 5 was repeated except that 2-bromo-4,6-diphenylpyridine was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the title compound Cpd17 70%). HRMS [M] &lt; + & gt ; : 591.202

[합성예 12] Cpd 18 (4-(7-([1,1':3',1''-terphenyl]-5'-yl)-9,10-dihydrophenanthren-2-yl)dibenzo[b,d]thiophene)의 합성Synthesis Example 12 Synthesis of Cpd 18 (4- (7 - ([1,1 ': 3', 1 "-terphenyl] -5'-yl) -9,10- dihydrophenanthren- d] thiophene

2-chloro-4,6-diphenyl-1,3,5-triazine 대신 1-Bromo-3,5-diphenylbenzene 를 사용하는 것을 제외하고는, 상기 합성예 5와 동일한 과정을 수행하여 표제 화합물 Cpd18 (수율 75%)을 얻었다. HRMS [M]+:590.206
The procedure of Synthetic Example 5 was repeated except that 1-Bromo-3,5-diphenylbenzene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain the title compound Cpd18 75%). HRMS [M] &lt; + & gt ; : 590.206

[[ 합성예Synthetic example 13]  13] CpdCpd 22 ( 22 ( 2,7-2,7- bisbis (9-(9- phenylphenyl -9H--9H- carbazolcarbazole -3--3- ylyl )-9,10-dihydrophenanthrene) -9,10-dihydrophenanthrene )의 합성) Synthesis of

Figure pat00013
Figure pat00013

<단계 1> 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydrophenanthrene 의 합성 Synthesis of 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9,10-dihydrophenanthrene

2,7-dibromo-9,10-dihydrophenanthrene (6.3g, 18.72mmol)과 Bis(pinacolate)diboron (11.9 g, 46.82mmol) 및 Pd(dppf)Cl2 (1.52 mg, 1.87 mmol), KOAc(7.3 g, 74.37mmol)를 플라스크에 넣고 질소 분위기 하에 톨루엔 120 ㎖에 용해시킨 후 12시간 동안 환류 교반하였다. TLC로 반응이 종결되는 것을 확인한 후 상온으로 식혔다. 반응 종료 후 증류수를 넣고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 화합물 (7.3g, 수율 90%)을 얻었다. HRMS [M]+:432.264(7.3 g, 18.72 mmol), Bis (pinacolate) diboron (11.9 g, 46.82 mmol) and Pd (dppf) Cl 2 (1.52 mg, 1.87 mmol) and KOAc , 74.37 mmol) were placed in a flask, dissolved in 120 ml of toluene under a nitrogen atmosphere, and then refluxed for 12 hours. After confirming that the reaction was terminated by TLC, the mixture was cooled to room temperature. After the reaction was completed, distilled water was added and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain a compound (7.3 g, yield 90%). HRMS [M] &lt; + & gt ; : 432.264

<단계 2> 2,7-bis(9-phenyl-9H-carbazol-3-yl)-9,10-dihydrophenanthrene 의 합성Synthesis of 2,7-bis (9-phenyl-9H-carbazol-3-yl) -9,10-dihydrophenanthrene

2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydrophenanthrene (6.6g, 15.34mmol)과 3-bromo-9-phenyl-9H-carbazole (12.3g, 38.17mmol) 및 Pd(PPh3)4 (1.8mg, 1.55mmol)을 플라스크에 넣고 2N Na2CO3 포화 수용액 92㎖와 1.4-dioxane 150 ㎖를 넣어 녹인 후 13시간 동안 가열교반하였다. Bromo-9-phenyl-9,10-dihydrophenanthrene (6.6 g, 15.34 mmol) and 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 9H-carbazole (12.3 g, 38.17 mmol) and Pd (PPh 3 ) 4 (1.8 mg, 1.55 mmol) were placed in a flask and 92 mL of a saturated aqueous solution of 2N Na 2 CO 3 and 150 mL of 1,4- Followed by heating and stirring.

반응 종료 후 증류수를 투여하고 에틸아세테이트로 추출하였다. 얻어진 유기층을 Na2SO4로 건조시키고 감압 증류한 다음 컬럼 크로마토그래피로 정제하여 표제 화합물(8.1g, 수율 80%)을 얻었다. HRMS [M]+:662.272
After completion of the reaction, distilled water was added thereto and extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and then purified by column chromatography to obtain the title compound (8.1 g, yield 80%). HRMS [M] &lt; + & gt ; : 662.272

[합성예 14] Cpd 27 (2,7-bis(4,6-diphenylpyrimidin-2-yl)-9,10-dihydrophenanthrene)의 합성Synthesis Example 14 Synthesis of Cpd 27 (2,7-bis (4,6-diphenylpyrimidin-2-yl) -9,10-dihydrophenanthrene)

3-bromo-9-phenyl-9H-carbazole 대신 2-chloro-4,6-diphenylpyrimidine 를 사용하는 것을 제외하고는, 상기 합성예 13과 동일한 과정을 수행하여 표제 화합물(수율 80%)을 얻었다. HRMS [M]+:640.262
The title compound (yield 80%) was obtained by following the procedure of Synthesis Example 13 while using 2-chloro-4,6-diphenylpyrimidine instead of 3-bromo-9-phenyl-9H-carbazole. HRMS [M] &lt; + & gt ; : 640.262

[합성예 15] Cpd 28 (2,7-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-9,10-dihydrophenanthrene)의 합성Synthesis Example 15 Synthesis of Cpd 28 (2,7-bis (4,6-diphenyl-1,3,5-triazin-2-yl) -9,10-dihydrophenanthrene)

3-bromo-9-phenyl-9H-carbazole 대신 2-chloro-4,6-diphenyl-1,3,5-triazine 를 사용하는 것을 제외하고는, 상기 합성예 13과 동일한 과정을 수행하여 표제 화합물(수율 80%)을 얻었다. HRMS [M]+:642.253
The procedure of Synthesis Example 13 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 3-bromo-9-phenyl-9H- Yield: 80%). HRMS [M] &lt; + & gt ; : 642.253

[합성예 16] Cpd 29 (2,7-bis(4,6-diphenylpyridin-2-yl)-9,10-dihydrophenanthrene)의 합성Synthesis Example 16 Synthesis of Cpd 29 (2,7-bis (4,6-diphenylpyridin-2-yl) -9,10-dihydrophenanthrene)

3-bromo-9-phenyl-9H-carbazole 대신 2-bromo-4,6-diphenylpyridine 를 사용하는 것을 제외하고는, 상기 합성예 13과 동일한 과정을 수행하여 표제 화합물(수율 80%)을 얻었다. HRMS [M]+:638.272
The title compound (yield 80%) was obtained by following the procedure of Synthesis Example 13 while using 2-bromo-4,6-diphenylpyridine instead of 3-bromo-9-phenyl-9H-carbazole. HRMS [M] &lt; + & gt ; : 638.272

[합성예 17] Cpd 30 (2,7-di([1,1':3',1''-terphenyl]-5'-yl)-9,10-dihydrophenanthrene)의 합성Synthesis Example 17 Synthesis of Cpd 30 (2,7-di ([1,1 ': 3', 1 "-terphenyl] -5'-yl) -9,10-dihydrophenanthrene

3-bromo-9-phenyl-9H-carbazole 대신 1-Bromo-3,5-diphenylbenzene를 사용하는 것을 제외하고는, 상기 합성예 13과 동일한 과정을 수행하여 표제 화합물(수율 80%)을 얻었다. HRMS [M]+:636.281
The title compound (yield 80%) was obtained by following the procedure of Synthesis Example 13 while using 1-Bromo-3,5-diphenylbenzene instead of 3-bromo-9-phenyl-9H-carbazole. HRMS [M] &lt; + & gt ; : 636.281

[[ 실시예Example 1 ~ 17] 녹색 유기  1 ~ 17] Green organic ELEL 소자의 제작 Device fabrication

앞서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 수행한 후 아래의 과정에 따라 녹색 유기 EL 소자를 제작하였다.The compound thus synthesized was subjected to high purity sublimation purification by a conventionally known method, and a green organic EL device was fabricated according to the following procedure.

먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ cpd(1, 4, 7-8, 11-18, 22, 27-30) 화합물 (각각) + 10 % Ir(ppy)3 (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. On the prepared ITO transparent electrode, a compound (each of m-MTDATA (60 nm) / TCTA (80 nm) / cpd (1, 4, 7-8, 11-18, 22, 27-30) + 10% Ir ) 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.

Figure pat00014
Figure pat00014

Figure pat00015
Figure pat00015

[비교예 1] 녹색 유기 EL 소자의 제작[Comparative Example 1] Production of green organic EL device

발광층 형성시 발광 호스트 물질로서 cpd (1, 4, 7-8, 11-18, 22, 27-30) 화합물 대신 CBP를 사용하는 것을 제외하고는, 실시예 1~17과 동일한 과정으로 녹색 유기 EL 소자를 제작하였다.
A green organic EL (organic electroluminescence) EL device was prepared in the same manner as in Examples 1 to 17 except that CBP was used in place of the compound cpd (1, 4, 7-8, 11-18, 22, 27-30) The device was fabricated.

[평가예 1][Evaluation Example 1]

실시예 1~17 및 비교예 1에서 제작한 각각의 녹색 유기 EL 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for each of the green organic EL devices manufactured in Examples 1 to 17 and Comparative Example 1, and the results are shown in Table 1 below.

샘플Sample 호스트Host 구동 전압
(V)Driving voltage
(V) EL 피크
(nm)EL peak
(nm) 전류효율
(cd/A)Current efficiency
(cd / A) 실시예 1Example 1 1One 6.786.78 515515 42.442.4 실시예 2Example 2 44 6.816.81 518518 41.141.1 실시예 3Example 3 77 6.796.79 517517 40.840.8 실시예 4Example 4 88 6.816.81 518518 41.141.1 실시예 5Example 5 1111 6.796.79 517517 40.840.8 실시예 6Example 6 1212 6.786.78 515515 42.442.4 실시예 7Example 7 1313 6.816.81 518518 41.141.1 실시예 8Example 8 1414 6.796.79 517517 40.840.8 실시예 9Example 9 1515 6.816.81 518518 41.141.1 실시예 10Example 10 1616 6.796.79 517517 40.840.8 실시예 11Example 11 1717 6.796.79 517517 40.840.8 실시예 12Example 12 1818 6.816.81 518518 41.141.1 실시예 13Example 13 2222 6.786.78 515515 42.442.4 실시예 14Example 14 2727 6.816.81 518518 41.141.1 실시예 15Example 15 2828 6.796.79 517517 40.840.8 실시예 16Example 16 2929 6.816.81 518518 41.141.1 실시예 17Example 17 3030 6.796.79 517517 40.840.8 비교예 1Comparative Example 1 CBPCBP 6.936.93 516516 38.238.2

상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물을 녹색 유기 EL 소자의 발광층으로 사용하는 실시예 1~17의 유기 EL 소자는 종래 CBP를 사용하는 비교예 1의 녹색 유기 EL 소자와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.
As shown in Table 1, the organic EL devices of Examples 1 to 17, in which the compound according to the present invention is used as a light emitting layer of a green organic EL device, are different from the green organic EL device of Comparative Example 1 using CBP It can be seen that it exhibits better performance in terms of efficiency and driving voltage.

[[ 실시예Example 18~34] 청색 유기  18 ~ 34] Blue organic ELEL 소자의 제조 Device manufacturing

앞서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 수행한 후 아래의 과정에 따라 청색 유기 EL 소자를 제작하였다.The compound thus synthesized was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic EL device was fabricated according to the following procedure.

먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

이렇게 준비된 ITO 투명 전극 위에 CuPc (10 nm)/ TPAC (30 nm)/ cpd(1, 4, 7-8, 11-18, 22, 27-30) 화합물 (각각) + 7 % Flrpic (30nm)/ Alq3 (30 nm)/ LiF (0.2 nm)/Al (150 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. (7 nm) / 7% Flrpic (30 nm) / cpd (1, 4, 7-8, 11-18, 22 and 27-30) compounds on the prepared ITO transparent electrode, Alq 3 (30 nm) / LiF (0.2 nm) / Al (150 nm) were stacked in this order to fabricate an organic EL device.

CuPc, TPAC, Flrpic의 구조는 하기와 같다.The structures of CuPc, TPAC, and Flrpic are as follows.

Figure pat00016
Figure pat00016

[비교예 2] 유기 EL 소자의 제작Comparative Example 2 Fabrication of Organic EL Device

발광층 형성시 발광 호스트 물질로서 cpd(1, 4, 7-8, 11-18, 22, 27-30) 화합물 대신 CBP를 사용하는 것을 제외하고는, 실시예 18~34와 동일한 과정으로 청색 유기 EL 소자를 제작하였다.
The procedure of Examples 18 to 34 was repeated except that CBP was used instead of cpd (1, 4, 7-8, 11-18, 22, 27-30) as a luminescent host material in forming the light emitting layer. The device was fabricated.

[평가예 2][Evaluation Example 2]

실시예 18~34 및 비교예 2에서 제작한 각각의 청색 유기 EL 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 2에 나타내었다.The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for each of the blue organic EL devices manufactured in Examples 18 to 34 and Comparative Example 2, and the results are shown in Table 2 below.

샘플Sample 호스트Host 구동 전압
(V)Driving voltage
(V) EL 피크
(nm)EL peak
(nm) 전류효율
(cd/A)Current efficiency
(cd / A) 실시예 18Example 18 1One 7.227.22 471471 5.995.99 실시예 19Example 19 44 7.127.12 472472 5.855.85 실시예 20Example 20 77 7.007.00 472472 6.346.34 실시예 21Example 21 88 7.297.29 473473 6.906.90 실시예 22Example 22 1111 7.307.30 474474 6.346.34 실시예 23Example 23 1212 7.247.24 475475 6.556.55 실시예 24Example 24 1313 7.157.15 471471 6.946.94 실시예 25Example 25 1414 7.237.23 472472 6.256.25 실시예 26Example 26 1515 7.007.00 472472 6.346.34 실시예 27Example 27 1616 7.297.29 473473 6.906.90 실시예 28Example 28 1717 7.307.30 474474 6.346.34 실시예 29Example 29 1818 7.247.24 475475 6.556.55 실시예 30Example 30 2222 7.157.15 471471 6.946.94 실시예 31Example 31 2727 7.237.23 472472 6.256.25 실시예 32Example 32 2828 7.227.22 471471 5.995.99 실시예 33Example 33 2929 7.127.12 472472 5.855.85 실시예 34Example 34 3030 7.007.00 472472 6.346.34 비교예 2Comparative Example 2 CBPCBP 7.807.80 474474 5.805.80

상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 청색 유기 EL 소자의 발광층으로 사용하는 실시예 18~34의 유기 EL 소자는 종래 CBP를 사용하는 비교예 2의 청색 유기 EL 소자와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 2, the organic EL devices of Examples 18 to 34, in which the compound according to the present invention is used as a light emitting layer of a blue organic EL device, are different from the conventional blue organic EL devices of Comparative Example 2 using CBP It can be seen that it exhibits better performance in terms of efficiency and driving voltage.

Claims (8)

하기 화학식 1로 표시되는 화합물:
[화학식 1]
Figure pat00017

상기 식에서,
R1 및 R2는 서로 같거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기, -P(=O)RaRb, 치환 또는 비치환된 C3~C40의 시클로알킬기 및 치환 또는 비치환된 핵원자수 3 내지 40의 헤테로시클로알킬기로 이루어진 군에서 선택되거나, 또는 이들이 인접하는 기와 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리 또는 축합 헤테로방향족 고리를 형성하는 기이며,
Ra 및 Rb는 서로 같거나 또는 상이하며, 각각 독립적으로 치환 또는 비치환된 C6~C40의 아릴기, 치환 또는 비치환된 C1~C40의 알킬기, 치환 또는 비치환된 C2~C40의 알케닐기, 치환 또는 비치환된 C2~C40의 알키닐기, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기, 치환 또는 비치환된 C6~C40의 아릴옥시기, 치환 또는 비치환된 C1~C40의 알킬옥시기 및 치환 또는 비치환된 C3~C40의 시클로알킬기로 이루어진 군에서 선택되거나, 또는 이들이 인접하는 기와 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리 또는 축합 헤테로방향족 고리를 형성하는 기이다며,
여기서, 상기 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기 및 핵원자수 3 내지 40의 헤테로시클로알킬기는, 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환될 수 있다.A compound represented by the following formula (1):
[Chemical Formula 1]
Figure pat00017

In this formula,
R 1 and R 2 are the same or different and each independently represents hydrogen, deuterium, halogen, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 to C 40 alkenyl group, a substituted or unsubstituted C 2 ~ C 40 of the alkynyl group, a substituted or unsubstituted C 6 ~ C 40 aryl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, substituted or non-substituted of unsubstituted C 6 ~ C for 40 aryloxy group, a substituted or unsubstituted C 1 ~ alkyloxy group of C 40, -P (= O) R a R b, a substituted or unsubstituted C 3 ~ C 40 cycloalkyl group and a substituted or Or a heterocycloalkyl group having 3 to 40 unsubstituted nucleus atoms or a group which forms a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with the adjacent groups,
R a and R b are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 40 aryl group, a substituted or unsubstituted C 1 to C 40 alkyl group, a substituted or unsubstituted C 2 ~ C 40 alkenyl group, a substituted or unsubstituted C 2 ~ C 40 of the alkynyl group, a substituted or unsubstituted nuclear atoms of 5 to 40 heteroaryl group, a substituted or unsubstituted C 6 ~ aryloxy of C 40 Or a substituted or unsubstituted C 1 -C 40 alkyloxy group and a substituted or unsubstituted C 3 -C 40 cycloalkyl group, or an adjacent group and a condensed aliphatic ring, a condensed aromatic ring, Group to form a condensed heteroaliphatic ring or a condensed heteroaromatic ring,
Wherein the C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 3 ~ cycloalkyl and nuclear atoms, 3 to heterocycloalkyl group 40 of C 40 are each independently a heavy hydrogen, a halogen, a cyano group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 -C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, C 6 to C 40 arylalkyl group, C 3 to C 40 cycloalkyl group, C 3 to C 40 It may be substituted with one or more substituents selected from the group consisting of a heterocycloalkyl group, a C 1 ~ C 40 alkylsilyl group, and a C 6 ~ C 40 arylsilyl group. 제1항에 있어서,
상기 R1 및 R2 는 서로 같거나 또는 상이하며, 각각 독립적으로 C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기이거나, 또는 이들이 인접하는 기와 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리 또는 축합 헤테로방향족 고리를 형성하는 기이며,
상기 C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환되는 것을 특징으로 하는 화합물.The method of claim 1,
Wherein R 1 and R 2 to each other the same or different and each independently C 6 ~ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, either of, or a group condensed aliphatic ring, a fused aromatic ring to which they are adjacent , A group forming a condensed heteroaliphatic ring or a condensed heteroaromatic ring,
The C 6 ~ C 40 aryl group, the heteroaryl group of 5 to 40 nuclear atoms are each independently deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, C 6 -C 40 arylalkyl group, C 3 -C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 1 -C 40 alkylsilyl group, and C 6 -C 40 Compound which is substituted with at least one substituent selected from the group consisting of an arylsilyl group of. 제1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 2 또는 화학식 3으로 표시되는 화합물인 것을 특징으로 하는 화합물:
[화학식 2]
Figure pat00018

[화학식 3]
Figure pat00019

상기 식에서,
X1 내지 X10는 서로 같거나 또는 상이하며, 각각 독립적으로 C 또는 N이며,
R3 내지 R16는 서로 같거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 C1~C10의 알킬기, 치환 또는 비치환된 C2~C10의 알케닐기, 치환 또는 비치환된 C2~C10의 알키닐기, 치환 또는 비치환된 C6~C8의 아릴기, 치환 또는 비치환된 핵원자수 5 내지 8의 헤테로아릴기, 치환 또는 비치환된 C3~C10의 시클로알킬기 및 치환 또는 비치환된 핵원자수 3 내지 10의 헤테로시클로알킬기로 이루어진 군에서 선택되며,
여기서, 상기 C1~C10의 알킬기, C2~C10의 알케닐기, C2~C10의 알키닐기, C6~C8의 아릴기, 핵원자수 5 내지 8의 헤테로아릴기, C3~C10의 시클로알킬기 및 핵원자수 3 내지 10의 헤테로시클로알킬기는, 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, 및 C6~C40의 아릴실릴기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환될 수 있다. The compound of claim 1, wherein the compound represented by Chemical Formula 1 is a compound represented by the following Chemical Formula 2 or Chemical Formula 3:
(2)
Figure pat00018

(3)
Figure pat00019

In this formula,
X 1 to X 10 are the same or different and are each independently C or N,
R 3 to R 16 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, substituted or unsubstituted C 1 to C 10 alkyl group, substituted or unsubstituted C 2 to C 10 alkenyl group, substituted Or unsubstituted C 2 to C 10 alkynyl group, substituted or unsubstituted C 6 to C 8 aryl group, substituted or unsubstituted heteroaryl group having 5 to 8 nuclear atoms, substituted or unsubstituted C 3 It is selected from the group consisting of a cycloalkyl group of ~ C 10 and a substituted or unsubstituted heterocycloalkyl group having 3 to 10 nuclear atoms,
Here, the C 1 ~ C 10 Alkyl group, C 2 ~ C 10 Alkenyl group, C 2 ~ C 10 Alkynyl group, C 6 ~ C 8 Aryl group, Nuclear atoms of 5 to 8 heteroaryl group, C 3 or heterocycloalkyl group of C 10 cycloalkyl group and the number of nuclear atoms of 3 to 10 are each independently a heavy hydrogen, a halogen, a cyano group, an alkenyl group of C 1 ~ C 40 alkyl group, C 2 ~ C 40 of, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, C 6 -C 40 arylalkyl group, C 3 -C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 1 -C 40 alkylsilyl group, and C 6 -C 40 It may be substituted with one or more substituents selected from the group consisting of an arylsilyl group. 제3항에 있어서, 상기 화학식 2로 표시되는 화합물은 하기 화학식으로 표시된 화합물 군에서 선택되는 것을 특징으로 하는 화합물:
Figure pat00020
The compound of claim 3, wherein the compound represented by Chemical Formula 2 is selected from the group of compounds represented by the following chemical formulas:
Figure pat00020
 제3항에 있어서, 상기 화학식 3으로 표시되는 화합물은 하기 화학식으로 표시된 화합물 군에서 선택되는 것을 특징으로 하는 화합물:
Figure pat00021

Figure pat00022
The compound of claim 3, wherein the compound represented by Chemical Formula 3 is selected from the group of compounds represented by the following chemical formulas:
Figure pat00021

Figure pat00022
 제1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식으로 표시된 화합물 군에서 선택되는 것을 특징으로 하는 화합물:
Figure pat00023

Figure pat00024

Figure pat00025
The compound of claim 1, wherein the compound represented by Chemical Formula 1 is selected from the group of compounds represented by the following chemical formulas:
Figure pat00023

Figure pat00024

Figure pat00025
 (i) 양극, (ⅱ) 음극, 및 (ⅲ) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,
상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 내지 제6항 중 어느 한 항에 따른 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자. An organic electroluminescent device comprising: (i) a cathode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
At least one of the one or more organic material layer comprises an compound according to any one of claims 1 to 6 characterized in that the organic electroluminescent device. 제 7 항에 있어서, 상기 화합물을 포함하는 유기물층은 발광층, 전자 수송층 및 정공 수송층으로 구성된 군으로부터 선택된 적어도 하나인 것을 특징으로 하는 유기 전계 발광 소자. The organic electroluminescent device according to claim 7, wherein the organic material layer including the compound is at least one selected from the group consisting of a light emitting layer, an electron transporting layer, and a hole transporting layer.
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