KR101983991B1

KR101983991B1 - Condensed aryl compound and organic light-diode including the same

Info

Publication number: KR101983991B1
Application number: KR1020120038093A
Authority: KR
Inventors: 제종태; 최성근; 김남이; 김희대
Original assignee: 에스에프씨 주식회사
Priority date: 2011-04-13
Filing date: 2012-04-12
Publication date: 2019-05-30
Also published as: KR20120116881A

Abstract

본 발명은 축합아릴 화합물 및 이를 발광물질로 포함하는 유기전계발광 소자에 관한 것으로서, 구체적으로 하기 [화학식 1]로 표시되는 축합아릴 화합물 및 이를 포함하는 유기전계발광소자인 것을 특징으로 하며, 본 발명에 따른 하기 [화학식 1]의 발광 화합물을 포함하는 유기전계발광소자는 구동전압, 전류효율 등의 발광특성에 있어 우수한 효과가 있다.
[화학식 1]

The present invention relates to a condensed aryl compound and an organic electroluminescent device comprising the same as a light emitting material, and more particularly to a condensed aryl compound represented by the following formula (1) and an organic electroluminescent device including the condensed aryl compound. The organic electroluminescent device comprising the luminescent compound of the following formula (1) according to the present invention has an excellent effect on the luminescent characteristics such as the driving voltage and the current efficiency.
[Chemical Formula 1]

Description

축합아릴 화합물 및 이를 포함하는 유기전계발광소자{Condensed aryl compound and organic light-diode including the same}[0001] The present invention relates to a condensed aryl compound and an organic electroluminescent device including the condensed aryl compound,

본 발명은 신규한 축합아릴 화합물 및 이를 발광물질로 포함하는 유기전계발광소자에 관한 것으로서, 보다 상세하게는 구동전압, 전류효율 등의 발광 특성이 우수하고, 보다 안정적인 신규한 축합아릴 화합물 및 이를 포함하는 유기전계발광소자에 관한 것이다.The present invention relates to a novel condensed aryl compound and an organic electroluminescent device including the same as a light emitting material. More particularly, the present invention relates to a novel condensed aryl compound having excellent light emitting properties such as driving voltage and current efficiency, To an organic electroluminescent device.

최근 표시장치의 대형화에 따라 공간 점유가 작은 평면표시소자의 요구가 증대되고 있는데, 대표적인 평면표시소자인 액정 디스플레이는 기존의 CRT(cathode ray tube)에 비해 경량화가 가능하다는 장점은 있으나, 시야각(viewing angle)이 제한되고 배면 광(back light)이 반드시 필요하다는 등의 단점을 갖고 있다. 이에 반하여, 새로운 평면표시소자인 유기전계발광소자(organic light emitting diode, OLED)는 자기 발광 현상을 이용한 디스플레이로서, 시야각이 크고, 액정 디스플레이에 비해 경박, 단소해질 수 있으며, 빠른 응답 속도 등의 장점을 가지고 있으며, 최근에는 풀-컬러(full-color) 디스플레이 또는 조명으로의 응용이 기대되고 있다.In recent years, the demand for a flat display device having a small space occupation has been increasing due to the enlargement of a display device. The liquid crystal display, which is a typical flat display device, has an advantage of being lighter than a conventional CRT (cathode ray tube) angle is limited and a back light is necessarily required. On the other hand, an organic light emitting diode (OLED), which is a new flat display device, is a display using a self-luminous phenomenon and has a wide viewing angle and can be made thinner and thinner than a liquid crystal display, And in recent years, application to a full-color display or illumination is expected.

일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다.In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

유기 발광 현상을 이용하는 유기전계발광소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기전계발광소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기전계발광소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기전계발광소자는 자발광, 고휘도, 고효율, 낮은 구동전압, 넓은 시야각, 높은 콘트라스트, 고속 응답성 등의 특성을 갖는 것으로 알려져 있다.An organic electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of the organic electroluminescent 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 it falls back to the ground state, the light comes out. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

유기전계발광소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.A material used as an organic material layer in an organic electroluminescent device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트-도판트 시스템을 사용할 수 있다.On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light-emitting material in order to increase the light-emitting efficiency through the light-emitting layer.

그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때, 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

유기전계발광소자가 전술한 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전계발광소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서, 당 기술분야에서는 새로운 재료의 개발이 계속 요구되고 있는 실정이다.In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material However, the development of a stable and efficient organic material layer material for an organic electroluminescence device has not been sufficiently developed yet. Therefore, there is a continuing need in the art for the development of new materials.

본 발명이 이루고자 하는 기술적 과제는 구동전압이 낮고 발광효율이 우수한 특성을 갖는 신규한 축합아릴 화합물을 제공하는 것이다.SUMMARY OF THE INVENTION The present invention provides a novel condensed aryl compound having a low driving voltage and a high luminous efficiency.

본 발명이 이루고자 하는 두 번째 기술적 과제는 상기 신규한 축합아릴 화합물을 포함하는 유기전계발광소자를 제공하는 것이다.A second object of the present invention is to provide an organic electroluminescent device comprising the novel condensed aryl compound.

따라서, 본 발명은 상기 첫 번째 기술적 과제를 달성하기 위하여,Accordingly, in order to accomplish the first technical object of the present invention,

하기 [화학식 1]로 표시되는 축합아릴 화합물을 제공한다.There is provided a condensed aryl compound represented by the following formula (1).

[화학식 1][Chemical Formula 1]

상기 [화학식 1]에서,In the above formula (1)

상기 X는 O, S, P, NR₅, CR₅R₆ 또는 SiR₅R₆이고, 상기 R₁ 내지 R₆, A₁, A₂, B₁ 및 B₂는 서로 동일하거나 상이하며,Wherein X is O, S, P, NR _5, CR ₅ R ₆ or a SiR ₅ R _6, wherein R ₁ to _{_{_{R 6, A 1, A 2}}} , B 1 and B ₂ are the same or different, and,

상기 R₁ 내지 R₆, A₁, A₂, B₁ 및 B₂는 각각 독립적으로 수소 원자, 중수소 원자, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실리콘기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기, 카르보닐기, 포스포릴기, 아미노기, 니트릴기, 히드록시기, 니트로기, 할로겐기, 아미드기 및 에스테르기로 이루어진 군에서 선택되고,Wherein R ₁ to R ₆ , A ₁ , A ₂ , B ₁ and B ₂ each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number 6 A substituted or unsubstituted aryloxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, Or an unsubstituted or substituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S, Or beach A substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxyl group, a nitro group, a halogen group, an amide group and an ester group,

상기 L₁ 및 L₂는 화학결합 또는 2가의 연결기로서 치환 또는 비치환된 탄소수 1 내지 30의 알킬렌기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐렌기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬렌기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기, 치환 또는 비치환된 탄소수 3 내지 50의 헤테로아릴렌기로 이루어진 군에서 선택될 수 있다.Wherein L ₁ and L ₂ are a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted C3 to C30 A substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms, and the like.

본 발명의 일 실시예에 의하면, 상기 R₁ 내지 R₆, A₁, A₂, B₁, B₂, L₁ 및 L₂는 수소 원자, 중수소 원자, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실리콘기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기, 카르보닐기, 포스포릴기, 아미노기, 니트릴기, 니트로기, 히드록시기, 할로겐기, 아미드기 및 에스테르기로 이루어진 군으로부터 1종 이상으로 더 치환될 수 있다.According to an embodiment of the present invention, R ₁ to R ₆ , A ₁ , A ₂ , B ₁ , B ₂ , L ₁ and L ₂ are each a hydrogen atom, a deuterium atom, a substituted or unsubstituted An alkyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1- A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroatom, O, N or S Having 3 to 50 carbon atoms An aryl group, a substituted or unsubstituted silicon group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a nitro group, a hydroxyl group, a halogen group, Group, and the like.

본 발명의 다른 일 실시예에 의하면, 상기 R₁ 내지 R₆, A₁, A₂, B₁, B₂, L₁ ,L₂ 및 치환기는 서로 인접한 기와 지방족, 방향족, 지방족헤테로 또는 방향족헤테로의 축합고리를 형성하거나 스피로결합을 이룰 수 있다.According to another embodiment of the present invention, R ₁ to R ₆ , A ₁ , A ₂ , B ₁ , B ₂ , L ₁ , L ₂ and substituents are adjacent to each other and an aliphatic, aromatic, aliphatic or aromatic hetero To form a condensed ring or to form a spiro bond.

본 발명은 상기 두 번째 기술적 과제를 달성하기 위하여,In order to achieve the second technical object of the present invention,

애노드, 캐소드 및상기 애노드와 상기 캐소드 사이에 개재되며, 상기 [화학식 1]로 표시되는 축합아릴 화합물을 포함하는 유기전계발광소자를 제공한다.There is provided an organic electroluminescent device comprising an anode, a cathode, and a condensed aryl compound interposed between the anode and the cathode, the condensed aryl compound being represented by Formula 1 below.

본 발명에 따르면, [화학식 1]로 표시되는 축합아릴 화합물은 기존 물질에 비하여 안정적이고 우수한 발광 특성을 가지므로 이를 포함하는 유기전계발광 소자는 저전압 구동이 가능하고 발광효율을 개선시킬 수 있다.According to the present invention, the condensed aryl compound represented by the formula (1) has stable and excellent luminescent characteristics as compared with the existing materials, so that the organic electroluminescent device including the condensed aryl compound can be operated at a low voltage and improve the luminous efficiency.

도 1은 본 발명의 일 구체예에 따른 유기전계발광소자의 개략도이다.1 is a schematic view of an organic electroluminescent device according to one embodiment of the present invention.

이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.

본 발명은 유기전계소자의 발광층에 포함되는 신규한 축합아릴 화합물로서, 상기 [화학식 1]로 표시되는 화합물인 것을 특징으로 한다.The present invention is a novel condensed aryl compound contained in the light emitting layer of an organic electroluminescent device, and is characterized by being a compound represented by the above formula (1).

본 발명에 따른 상기 [화학식 1]의 축합아릴 화합물에 있어서, 그 치환기를 보다 구체적으로 설명하면 하기와 같다.In the condensed aryl compound of the formula (1) according to the present invention, the substituent will be described in more detail as follows.

상기 R₁ 내지 R₆, A₁, A₂, B₁, B₂, L₁ 및 L₂는 수소 원자, 중수소 원자, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실리콘기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기, 카르보닐기, 포스포릴기, 아미노기, 니트릴기, 니트로기, 히드록시기, 할로겐기, 아미드기 및 에스테르기로 이루어진 군으로부터 1종 이상으로 더 치환될 수 있는 것을 특징으로 한다.Wherein R ₁ to R ₆ , A ₁ , A ₂ , B ₁ , B ₂ , L ₁ and L _{2 each} represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, a substituted or unsubstituted C1- A substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a heteroaryl group having 3 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S, Group, a substituted or unsubstituted silyl At least one group selected from the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, And can be substituted.

또한, 상기 R₁ 내지 R₆, A₁, A₂, B₁, B₂, L₁, L₂ 및 치환기는 서로 인접한 기와 지방족, 방향족, 지방족헤테로 또는 방향족헤테로의 축합고리를 형성하거나 스피로결합을 이룰 수 있다.The substituents R ₁ to R ₆ , A ₁ , A ₂ , B ₁ , B ₂ , L ₁ and L ₂ may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with an adjacent group, Can be achieved.

본 발명에 있어서, "치환 또는 비치환된"이라는 용어는 아릴기, 헤테로아릴기, 알킬기, 헤테로알킬기, 사이클로알킬기, 알콕시기, 시아노기, 할로겐기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 게르마늄, 인, 보론, 중수소 및 수소로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되는 것을 의미한다.In the present invention, the term "substituted or unsubstituted" means an aryl group, a heteroaryl group, an alkyl group, a heteroalkyl group, a cycloalkyl group, an alkoxy group, a cyano group, a halogen group, an aryloxy group, an alkylsilyl group, , Germanium, phosphorus, boron, deuterium and hydrogen. The term " substituted or unsubstituted "

상술한 바와 같은 구조를 갖는 상기 [화학식 1]에 따른 신규한 축합아릴 화합물에 대한 구체적인 예에 의해서 본 발명이 제한되는 것은 아니지만, 구체적으로 하기 [화학식 2] 내지 [화학식 49]로 표시되는 화합물 중 어느 하나일 수 있다.The present invention is not limited by the specific examples of the novel condensed aryl compound according to the above formula (1) having the above-mentioned structure, but specifically, among the compounds represented by the following formulas (2) to It can be either.

[화학식 2] [화학식 3][Chemical Formula 2] < EMI ID =

[화학식 4] [화학식 5][Chemical Formula 4]

[화학식 6] [화학식 7][Chemical Formula 6] < EMI ID =

[화학식 8] [화학식 9][Chemical Formula 8]

[화학식 10] [화학식 11][Chemical Formula 10]

[화학식 12] [화학식 13][Chemical Formula 12]

[화학식 14] [화학식 15][Chemical Formula 14]

[화학식 16] [화학식 17][Chemical Formula 16]

[화학식 18] [화학식 19][Chemical Formula 18]

[화학식 20] [화학식 21][Chemical Formula 20]

[화학식 22] [화학식 23][Chemical Formula 22]

[화학식 24] [화학식 25][Chemical Formula 24]

[화학식 26] [화학식 27][Chemical Formula 26]

[화학식 28] [화학식 29][Chemical Formula 28]

[화학식 30] [화학식 31][Chemical Formula 30]

[화학식 32] [화학식 33][Chemical Formula 32]

[화학식 34] [화학식 35][Chemical Formula 35]

[화학식 36] [화학식 37][Chemical Formula 36]

[화학식 38] [화학식 39][Chemical Formula 38]

[화학식 40] [화학식 41][Chemical Formula 40]

[화학식 42] [화학식 43][Chemical Formula 42]

[화학식 44] [화학식 45][Chemical Formula 44]

[화학식 46] [화학식 47][Chemical Formula 46]

[화학식 48] [화학식 49][Chemical Formula 48]

또한, 본 발명에 따른 상기 [화학식 1]에 따른 신규한 축합아릴 화합물은 구체적으로 하기 [화학식 50] 내지 [화학식 1265]로 표시되는 화합물 중 어느 하나일 수 있다.The novel condensed aryl compound according to the present invention may be any of the compounds represented by the following formulas (50) to (1265).

[화학식50] [화학식51] [화학식52] [화학식53][Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]

[화학식54] [화학식55] [화학식56] [화학식57][Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[화학식58] [화학식59] [화학식60] [화학식61][Chemical Formula 60] [Chemical Formula 61]

[화학식62] [화학식63] [화학식64] [화학식65][Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 65]

[화학식66] [화학식67] [화학식68] [화학식69][Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69]

[화학식70] [화학식71] [화학식72] [화학식73]

[Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73]

[화학식74] [화학식75] [화학식76] [화학식77]

[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77]

[화학식78] [화학식79] [화학식80] [화학식81]

[Formula 79] [Formula 80] [Formula 81]

[화학식82] [화학식83] [화학식84] [화학식85]

[Chemical Formula 82]

[화학식86] [화학식87] [화학식88] [화학식89]

[Chemical Formula 88] [Chemical Formula 88] [Chemical Formula 89]

[화학식90] [화학식91] [화학식92] [화학식93]

[Chemical Formula 91] [Chemical Formula 92] [Chemical Formula 93]

[화학식94] [화학식95] [화학식96] [화학식97]

[Chemical Formula 95] [Chemical Formula 96] [Chemical Formula 97]

[화학식98] [화학식99] [화학식100] [화학식101]

[Chemical Formula 100] [Chemical Formula 100]

[화학식102] [화학식103] [화학식104] [화학식105]

[Formula 103] [Formula 103]

[화학식106] [화학식107] [화학식108] [화학식109]

[Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10] [Chemical Formula 10]

[화학식110] [화학식111] [화학식112] [화학식113]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[화학식114] [화학식115] [화학식116] [화학식117]

[Chemical Formula 115]

[화학식118] [화학식119] [화학식120] [화학식121]

[Chemical Formula 120] [Chemical Formula 120] [Chemical Formula 120]

[화학식122] [화학식123] [화학식124] [화학식125]

[Formula 124] [Formula 124] [Formula 125]

[화학식126] [화학식127] [화학식128] [화학식129]

[Formula 126] < EMI ID = 129.1 >

[화학식130] [화학식131] [화학식132] [화학식133]

[Formula 130] < EMI ID = 131.0 >

[화학식134] [화학식135] [화학식136] [화학식137]

[Formula 135] [Formula 135] [Formula 137]

[화학식138] [화학식139] [화학식140] [화학식141]

[Chemical Formula 140] [Chemical Formula 140] [Chemical Formula 140]

[화학식142] [화학식143] [화학식144] [화학식145]

[Chemical Formula 144] [Chemical Formula 144] [Chemical Formula 145]

[화학식146] [화학식147] [화학식148] [화학식149]

[Chemical Formula 146] [Chemical Formula 148] [Chemical Formula 149]

[화학식150] [화학식151] [화학식152] [화학식153]

[Formula 15] [Formula 15] [Formula 15] [Formula 15]

[화학식154] [화학식155] [화학식156] [화학식157][Chemical Formula 155] [Chemical Formula 156] [Chemical Formula 157]

[화학식158] [화학식159] [화학식160] [화학식161][Formula 15] [Formula 15] [Formula 15] [Formula 15] [Formula 15]

[화학식162] [화학식163] [화학식164] [화학식165][166] [165] [165]

[화학식166] [화학식167] [화학식168] [화학식169][Formula 166] [Formula 169] [Formula 169]

[화학식170] [화학식171] [화학식172] [화학식173][173] [173] [173]

[화학식174] [화학식175] [화학식176] [화학식177][Formula 177] [Formula 177] [Formula 177]

[화학식178] [화학식179] [화학식180] [화학식181][Formula 181] [Formula 181] [Formula 181] [Formula 181]

[화학식182] [화학식183] [화학식184] [화학식185][Formula 182] [Formula 184] [Formula 184]

[화학식186] [화학식187] [화학식188] [화학식189][Formula 188] [Formula 188] [Formula 189]

[화학식190] [화학식191] [화학식192] [화학식193][Formula 19] [Formula 19] [Formula 193] [Formula 193]

[화학식194] [화학식195] [화학식196] [화학식197][Formula 19] [Formula 19] [Formula 19] [Formula 19] [Formula 19]

[화학식198] [화학식199] [화학식200] [화학식201][201] [201] [201]

[화학식202] [화학식203] [화학식204] [화학식205][Chemical Formula 203]

[화학식206] [화학식207] [화학식208] [화학식209][Chemical Formula 20] [Chemical Formula 20]

[화학식210] [화학식211] [화학식212] [화학식213][Chemical Formula 210] [Chemical Formula 212] [Chemical Formula 213]

[화학식214] [화학식215] [화학식216] [화학식217][Formula 21] [Formula 21] [Formula 21] [Formula 21]

[화학식218] [화학식219] [화학식220] [화학식221][Formula 21] < EMI ID =

[화학식222] [화학식223] [화학식224] [화학식225][Formula 22] < EMI ID =

[화학식226] [화학식227] [화학식228] [화학식229][229] [229] [229]

[화학식230] [화학식231] [화학식232] [화학식233][233] [232] [233]

[화학식234] [화학식235] [화학식236] [화학식237][237] [237] [237]

[화학식238] [화학식239] [화학식240] [화학식241][238] [240] [248]

[화학식242] [화학식243] [화학식244] [화학식245][245] [242] [242]

[화학식246] [화학식247] [화학식248] [화학식249][248] [248] [249]

[화학식250] [화학식251] [화학식252] [화학식253][Formula 252] [Formula 253]

[화학식254] [화학식255] [화학식256] [화학식257][Formula 25] [Formula 25] [Formula 25] [Formula 25]

[화학식258] [화학식259] [화학식260] [화학식261][Formula 252] [Chemical Formula 260] [Chemical Formula 261]

[화학식262] [화학식263] [화학식264] [화학식265][Formula 262] [Formula 264] [Formula 265]

[화학식266] [화학식267] [화학식268] [화학식269][268] [268] [268] [269]

[화학식270] [화학식271] [화학식272] [화학식273][273] [272] [272] [272]

[화학식274] [화학식275] [화학식276] [화학식277](277) [Formula 277] [Formula 277]

[화학식278] [화학식279] [화학식280] [화학식281](281) [Chemical Formula 280] [Chemical Formula 280]

[화학식282] [화학식283] [화학식284] [화학식285][Formula 28] [Formula 28] [Formula 28]

[화학식286] [화학식287] [화학식288] [화학식289][Formula 288] [Formula 288] [Formula 289]

[화학식290] [화학식291] [화학식292] [화학식293][290] [290] [292] [293]

[화학식294] [화학식295] [화학식296] [화학식297](297) [Chemical Formula 297] [Chemical Formula 297]

[화학식298] [화학식299] [화학식300] [화학식301][Chemical Formula 300] [Chemical Formula 301]

[화학식302] [화학식303] [화학식304] [화학식305][Chemical Formula 303] [Chemical Formula 304]

[화학식306] [화학식307] [화학식308] [화학식309][Formula 309] [Formula 309]

[화학식310] [화학식311] [화학식312] [화학식313][311] [311] [313] [313]

[화학식314] [화학식315] [화학식316] [화학식317][314] [315] [316]

[화학식318] [화학식319] [화학식320] [화학식321][311] [318] [320]

[화학식322] [화학식323] [화학식324] [화학식325](325), wherein R < 1 >

[화학식326] [화학식327] [화학식328] [화학식329][328] [328] [329]

[화학식330] [화학식331] [화학식332] [화학식333][333] [333] [333]

[화학식334] [화학식335] [화학식336] [화학식337](337) [Chemical Formula 337] [Chemical Formula 337]

[화학식338] [화학식339] [화학식340] [화학식341][331] [333] [340] [341]

[화학식342] [화학식343] [화학식344] [화학식345](345) [Formula 344] [Formula 345]

[화학식346] [화학식347] [화학식348] [화학식349][Chemical Formula 347] [Chemical Formula 349] [Chemical Formula 349]

[화학식350] [화학식351] [화학식352] [화학식353][353] [353] [353]

[화학식354] [화학식355] [화학식356] [화학식357](357) [Chemical Formula 357] [Chemical Formula 357]

[화학식358] [화학식359] [화학식360] [화학식361][Formula 35] [Formula 35] [Formula 35]

[화학식362] [화학식363] [화학식364] [화학식365](365) [Chemical Formula 365] [Chemical Formula 365]

[화학식366] [화학식367] [화학식368] [화학식369][368] [369] [369] [369]

[화학식370] [화학식371] [화학식372] [화학식373][370] [370]

[화학식374] [화학식375] [화학식376] [화학식377][Formula 377] [Formula 377] [Formula 377]

[화학식378] [화학식379] [화학식380] [화학식381][380] [380] [380] [380]

[화학식382] [화학식383] [화학식384] [화학식385][Formula 38] [Formula 384] [Formula 385]

[화학식386] [화학식387] [화학식388] [화학식389][Formula 388] [Formula 388] [Formula 389]

[화학식390] [화학식391 ] [화학식392] [화학식393][390] [390] [393] [393]

[화학식394] [화학식395] [화학식396] [화학식397][397] [396] [396]

[화학식398] [화학식399] [화학식400] [화학식401][Formula 39] [Formula 39] [Formula 39]

[화학식402] [화학식403] [화학식404] [화학식405][402] [40] [40] [40] [40]

[화학식406] [화학식407] [화학식408] [화학식409][Chemical Formula 409] [Chemical Formula 409]

[화학식410] [화학식411] [화학식412] [화학식413][410] [410] [411] [411]

[화학식414] [화학식415] [화학식416] [화학식417](417) [Chemical Formula 417] [Chemical Formula 417]

[화학식418] [화학식419] [화학식420] [화학식421][Formula 41] [Formula 41]

[화학식422] [화학식423] [화학식424] [화학식425][422] [422] [422] [422]

[화학식426] [화학식427] [화학식428] [화학식429][428] [428] [428] [429]

[화학식430] [화학식431] [화학식432] [화학식433][Chemical Formula 433] [Chemical Formula 433] [Chemical Formula 433]

[화학식434] [화학식435] [화학식436] [화학식437][Chemical Formula 437] [Chemical Formula 437] [Chemical Formula 437]

[화학식438] [화학식439] [화학식440] [화학식441][Formula 43] [Formula 43] [Formula 43]

[화학식442] [화학식443] [화학식444] [화학식445][Chemical Formula 445] [Chemical Formula 445] [Chemical Formula 445]

[화학식446] [화학식447] [화학식448] [화학식449][Chemical Formula 447] [Chemical Formula 449] [Chemical Formula 449]

[화학식450] [화학식451] [화학식452] [화학식453][Formula 45] [Formula 453] [Formula 453]

[화학식454] [화학식455] [화학식456] [화학식457][Chemical Formula 457] [Chemical Formula 457] [Chemical Formula 457]

[화학식458] [화학식459] [화학식460] [화학식461][Formula 456] [Formula 460] [Formula 461]

[화학식462] [화학식463] [화학식464] [화학식465][Chemical Formula 463] [Chemical Formula 465] [Chemical Formula 465]

[화학식466] [화학식467] [화학식468] [화학식469][Formula 466] [Formula 466] [Formula 469]

[화학식470] [화학식471] [화학식472] [화학식473][Formula 472] [Formula 472] [Formula 473]

[화학식474] [화학식475] [화학식476] [화학식477][Chemical Formula 477] [Chemical Formula 477] [Chemical Formula 477]

[화학식478] [화학식479] [화학식480] [화학식481][488] [488] [488] [488]

[화학식482] [화학식483] [화학식484] [화학식485][Formula 48] [Formula 48] [Formula 48]

[화학식486] [화학식487] [화학식488] [화학식489][488] [488] [488] [488] [488]

[화학식490] [화학식491] [화학식492] [화학식493][Formula 49] [Formula 493] [Formula 493]

[화학식494] [화학식495] [화학식496] [화학식497][Chemical Formula 497] [Chemical Formula 497] [Chemical Formula 497]

[화학식498] [화학식499] [화학식500] [화학식501][Formula 49] [Chemical Formula 500] [Chemical Formula 501]

[화학식502] [화학식503] [화학식504] [화학식505][Chemical Formula 503] [Chemical Formula 505]

[화학식506] [화학식507] [화학식508] [화학식509][Formula 508] [Formula 509]

[화학식510] [화학식511] [화학식512] [화학식513][510] [511] [512]

[화학식514] [화학식515] [화학식516] [화학식517][514] [515] [515] [517]

[화학식518] [화학식519] [화학식520] [화학식521][518] [521] [521]

[화학식522] [화학식523] [화학식524] [화학식525][522] [522] [522] [522]

[화학식526] [화학식527] [화학식528] [화학식529][529] [528] [529]

[화학식530] [화학식531] [화학식532] [화학식533][533] [533] [533] [533]

[화학식534] [화학식535] [화학식536] [화학식537][Chemical Formula 537] [Chemical Formula 537] [Chemical Formula 537]

[화학식538] [화학식539] [화학식540] [화학식541][538] [539] [539]

[화학식542] [화학식543] [화학식544] [화학식545][545] [544] [544] [545]

[화학식546] [화학식547] [화학식548] [화학식549][549] [548] [548] [549]

[화학식550] [화학식551] [화학식552] [화학식553][551] [552] [552]

[화학식554] [화학식555] [화학식556] [화학식557][557] [557] [557] [557]

[화학식558] [화학식559] [화학식560] [화학식561][569] [569] [569]

[화학식562] [화학식563] [화학식564] [화학식565]565] [Chemical Formula 565] [Chemical Formula 565]

[화학식566] [화학식567] [화학식568] [화학식569][569] [569] [569] [569]

[화학식570] [화학식571] [화학식572] [화학식573][573] [572] [572] [572]

[화학식574] [화학식575] [화학식576] [화학식577](577) [Chemical Formula 577] [Chemical Formula 577] [Chemical Formula 577]

[화학식578] [화학식579] [화학식580] [화학식581][578] [589] [589]

[화학식582] [화학식583] [화학식584] [화학식585][582] [582] [582]

[화학식586] [화학식587] [화학식588] [화학식589][588] [588] [588] [589]

[화학식590] [화학식591] [화학식592] [화학식593][Formula 599] [Formula 593] [Formula 593]

[화학식594] [화학식595] [화학식596] [화학식597][Chemical Formula 597] [Chemical Formula 597] [Chemical Formula 597]

[화학식598] [화학식599] [화학식600] [화학식601][Chemical Formula 601] [Chemical Formula 601]

[화학식602] [화학식603] [화학식604] [화학식605][602] [603] [603]

[화학식606] [화학식607] [화학식608] [화학식609][608] [609] [609]

[화학식610] [화학식611] [화학식612] [화학식613][Formula 611] [Formula 611]

[화학식614] [화학식615] [화학식616] [화학식617][617] [616] [616]

[화학식618] [화학식619] [화학식620] [화학식621][618] [618] [618]

[화학식622] [화학식623] [화학식624] [화학식625][622] [622] [622] [622]

[화학식626] [화학식627] [화학식628] [화학식629][629] [629] [629]

[화학식630] [화학식631] [화학식632] [화학식633][Formula 633] [Formula 632] [Formula 633]

[화학식634] [화학식635] [화학식636] [화학식637][Formula 636] [Formula 636] [Formula 637]

[화학식638] [화학식639] [화학식640] [화학식641][638] [638] [638]

[화학식642] [화학식643] [화학식644] [화학식645](645) [0604] The compound of the formula (645)

[화학식646] [화학식647] [화학식648] [화학식649][Formula 648] [Formula 648]

[화학식650] [화학식651] [화학식652] [화학식653][653] [653] [653]

[화학식654] [화학식655] [화학식656] [화학식657][657] [657] [657] [657]

[화학식658] [화학식659] [화학식660] [화학식661][Formula 65] [Formula 65] [Formula 65]

[화학식662] [화학식663] [화학식664] [화학식665][663] [662] [662]

[화학식666] [화학식667] [화학식668] [화학식669][669] [669] [669]

[화학식670] [화학식671] [화학식672] [화학식673][Formula 673] [Formula 673] [Formula 673]

[화학식674] [화학식675] [화학식676] [화학식677](677) [Chemical Formula 677] [Chemical Formula 677] [Chemical Formula 677]

[화학식678] [화학식679] [화학식680] [화학식681][678] [678] [678]

[화학식682] [화학식683] [화학식684] [화학식685][688] [688] [688] [688]

[화학식686] [화학식687] [화학식688] [화학식689][688] [688] [688] [688]

[화학식690] [화학식691] [화학식692] [화학식693][692] [692] [692]

[화학식694] [화학식695] [화학식696] [화학식697][697] [697] [697] [697]

[화학식698] [화학식699] [화학식700] [화학식701][708] [709] [709]

[화학식702] [화학식703] [화학식704] [화학식705][703] [703] [705]

[화학식706] [화학식707] [화학식708] [화학식709][707] [709] [709] [709]

[화학식710] [화학식711] [화학식712] [화학식713][712] [712] [712] [712]

[화학식714] [화학식715] [화학식716] [화학식717][717] [717] [717]

[화학식718] [화학식719] [화학식720] [화학식721][721] [720] [720]

[화학식722] [화학식723] [화학식724] [화학식725][732] [722] [722] [722]

[화학식726] [화학식727] [화학식728] [화학식729][729] [729] [729] [729]

[화학식730] [화학식731] [화학식732] [화학식733][733] [733] [733]

[화학식734] [화학식735] [화학식736] [화학식737][737] [737] [737]

[화학식738] [화학식739] [화학식740] [화학식741][738] [739] [749]

[화학식742] [화학식743] [화학식744] [화학식745][Chemical Formula 744] [Chemical Formula 744] [Chemical Formula 745]

[화학식746] [화학식747] [화학식748] [화학식749][748] [748] [749] [749]

[화학식750] [화학식751] [화학식752] [화학식753][Formula 753] [Formula 753]

[화학식754] [화학식755] [화학식756] [화학식757][757] [757] [757] [757]

[화학식758] [화학식759] [화학식760] [화학식761][Formula 756] [Formula 756] [Formula 751]

[화학식762] [화학식763] [화학식764] [화학식765][763] [763] [764] [765]

[화학식766] [화학식767] [화학식768] [화학식769][Formula 766] [Chemical Formula 769] [Chemical Formula 769]

[화학식770] [화학식771] [화학식772] [화학식773][773] [772] [772]

[화학식774] [화학식775] [화학식776] [화학식777][777] [777] [777] [777]

[화학식778] [화학식779] [화학식780] [화학식781][Formula 778] [Formula 780]

[화학식782] [화학식783] [화학식784] [화학식785][788] [788] [788] [788]

[화학식786] [화학식787] [화학식788] [화학식789][788] [788] [788] [788]

[화학식790] [화학식791] [화학식792] [화학식793][793] [792] [792]

[화학식794] [화학식795] [화학식796] [화학식797][797] [797] [797] [797]

[화학식798] [화학식799] [화학식800] [화학식801][Formula 798] [Formula 800] [Formula 801]

[화학식802] [화학식803] [화학식804] [화학식805][Formula 804] [Formula 804]

[화학식806] [화학식807] [화학식808] [화학식809][808] [808] [808]

[화학식810] [화학식811] [화학식812] [화학식813][812] [812] [812] [811]

[화학식814] [화학식815] [화학식816] [화학식817][Formula 814] [Formula 816] [Formula 816]

[화학식818] [화학식819] [화학식820] [화학식821][821] [820] [820]

[화학식822] [화학식823] [화학식824] [화학식825][822] [822] [824]

[화학식826] [화학식827] [화학식828] [화학식829][828] [828] [828] [829]

[화학식830] [화학식831] [화학식832] [화학식833](832) [Formula 832] [Formula 832]

[화학식834] [화학식835] [화학식836] [화학식837][837] [837] [837]

[화학식838] [화학식839] [화학식840] [화학식841][Formula 838] [Formula 840] [Formula 841]

[화학식842] [화학식843] [화학식844] [화학식845][842] [844] [844]

[화학식846] [화학식847] [화학식848] [화학식849][848] [848] [848] [848]

[화학식850] [화학식851] [화학식852] [화학식853][Formula 853] < EMI ID =

[화학식854] [화학식855] [화학식856] [화학식857][Formula 857] [Formula 857] [Formula 857]

[화학식858] [화학식859] [화학식860] [화학식861][868] [869] < EMI ID =

[화학식862] [화학식863] [화학식864] [화학식865][862] [863] [864]

[화학식866] [화학식867] [화학식868] [화학식869][868] [868] [869]

[화학식870] [화학식871] [화학식872] [화학식873][873] [872] [873] [873]

[화학식874] [화학식875] [화학식876] [화학식877][877] [877] [877] [877]

[화학식878] [화학식879] [화학식880] [화학식881][878] [878] [888] [888]

[화학식882] [화학식883] [화학식884] [화학식885][Formula 88] [Formula 88] [Formula 884]

[화학식886] [화학식887] [화학식888] [화학식889][Formula 888] [Formula 888] [Formula 889]

[화학식890] [화학식891] [화학식892] [화학식893][892] [892] [892]

[화학식894] [화학식895] [화학식896] [화학식897][897] [897] [897]

[화학식898] [화학식899] [화학식900] [화학식901][898] [909] [909]

[화학식902] [화학식903] [화학식904] [화학식905][Formula 903] [Formula 904]

[화학식906] [화학식907] [화학식908] [화학식909][Formula 908] [Formula 909] [Formula 909]

[화학식910] [화학식911] [화학식912] [화학식913][Formula 911] [Formula 912] [Formula 913]

[화학식914] [화학식915] [화학식916] [화학식917][Formula 914] [Formula 914]

[화학식918] [화학식919] [화학식920] [화학식921][921] [920]

[화학식922] [화학식923] [화학식924] [화학식925](925) [Formula 922] < EMI ID =

[화학식926] [화학식927] [화학식928] [화학식929][929] [929] [929] [929]

[화학식930] [화학식931] [화학식932] [화학식933][931] [931] [931]

[화학식934] [화학식935] [화학식936] [화학식937][936] [936] [936]

[화학식938] [화학식939] [화학식940] [화학식941][Chemical Formula 940] [Chemical Formula 940]

[화학식942] [화학식943] [화학식944] [화학식945][Chemical Formula 944] [Chemical Formula 944] [Chemical Formula 945]

[화학식946] [화학식947] [화학식948] [화학식949][Chemical Formula 947] [Chemical Formula 948] [Chemical Formula 949]

[화학식950] [화학식951] [화학식952] [화학식953][953] [952] [953]

[화학식954] [화학식955] [화학식956] [화학식957][Chemical Formula 957] [Chemical Formula 957] [Chemical Formula 957]

[화학식958] [화학식959] [화학식960] [화학식961][Chemical Formula 959]

[화학식962] [화학식963] [화학식964] [화학식965][Chemical Formula 965]

[화학식966] [화학식967] [화학식968] [화학식969][Chemical Formula 969] [Chemical Formula 969] [Chemical Formula 969]

[화학식970] [화학식971] [화학식972] [화학식973][973] [972] [973] [973]

[화학식974] [화학식975] [화학식976] [화학식977][977] [977] [977] [977]

[화학식978] [화학식979] [화학식980] [화학식981][Formula 978] [Formula 978]

[화학식982] [화학식983] [화학식984] [화학식985][982] [982] [982] [982]

[화학식986] [화학식987] [화학식988] [화학식989][988] [988] [988] [988]

[화학식990] [화학식991] [화학식992] [화학식993][Formula 99] [Formula 993] [Formula 993]

[화학식994] [화학식995] [화학식996] [화학식997][Formula 997] [Formula 997] [Formula 997]

[화학식998] [화학식999] [화학식1000] [화학식1001][Formula 991] [Chemical Formula 1000] [Chemical Formula 1001]

[화학식1002] [화학식1003] [화학식1004] [화학식1005][Formula 1003] [Formula 1004] [Formula 1005]

[화학식1006] [화학식1007] [화학식1008] [화학식1009](1009) [Chemical Formula 1009] [Chemical Formula 1009]

[화학식1010] [화학식1011] [화학식1012] [화학식1013][1010] [Chemical Formula 1011] [Chemical Formula 1013]

[화학식1014] [화학식1015] [화학식1016] [화학식1017]Wherein R < 1 > and R < 2 &

[화학식1018] [화학식1019] [화학식1020] [화학식1021]Embedded image In the formula,

[화학식1022] [화학식1023] [화학식1024] [화학식1025][1022] [1022] [1022]

[화학식1026] [화학식1027] [화학식1028] [화학식1029][1028] [1028] [1029]

[화학식1030] [화학식1031] [화학식1032] [화학식1033][0103] The compound of the formula [1030]

[화학식1034] [화학식1035] [화학식1036] [화학식1037][1036] [1036] [1036]

[화학식1038] [화학식1039] [화학식1040] [화학식1041][1038] [1038]

[화학식1042] [화학식1043] [화학식1044] [화학식1045][1045] [1045] [1045]

[화학식1046] [화학식1047] [화학식1048] [화학식1049][1049] [1048] [1049]

[화학식1050] [화학식1051] [화학식1052] [화학식1053][1053] [1053] [1053]

[화학식1054] [화학식1055] [화학식1056] [화학식1057][1057] [1055] [1055]

[화학식1058] [화학식1059] [화학식1060] [화학식1061][1069] [1069] [1069]

[화학식1062] [화학식1063] [화학식1064] [화학식1065][1066] [1066] [1066] [1066]

[화학식1066] [화학식1067] [화학식1068] [화학식1069][1066] [1069] [1066]

[화학식1070] [화학식1071] [화학식1072] [화학식1073](1073) [Formula 1073] < EMI ID =

[화학식1074] [화학식1075] [화학식1076] [화학식1077][1077] [Formula 1077] [Formula 1077]

[화학식1078] [화학식1079] [화학식1080] [화학식1081][1088] [1089] [1089]

[화학식1082] [화학식1083] [화학식1084] [화학식1085][1088] [1088] [1088] [1088]

[화학식1086] [화학식1087] [화학식1088] [화학식1089][1088] [1088] [1088] [1088]

[화학식1090] [화학식1091] [화학식1092] [화학식1093][1093] [1092] [1093]

[화학식1094] [화학식1095] [화학식1096] [화학식1097][1097] [1099] [1099]

[화학식1098] [화학식1099] [화학식1100] [화학식1101][Formula 1110] [Formula 1110] [Formula 1101]

[화학식1102] [화학식1103] [화학식1104] [화학식1105][Formula 110] [Formula 1104]

[화학식1106] [화학식1107] [화학식1108] [화학식1109][Formula 110] [Formula 1104]

[화학식1110] [화학식1111] [화학식1112] [화학식1113][Formula 1111] [Formula 1111] [Formula 1111] [Formula 1113]

[화학식1114] [화학식1115] [화학식1116] [화학식1117][Formula 1111] [Formula 1111]

[화학식1118] [화학식1119] [화학식1120] [화학식1121][Formula 1121] [Formula 1120]

[화학식1122] [화학식1123] [화학식1124] [화학식1125][Formula 1125] [Formula 1122]

[화학식1126] [화학식1127] [화학식1128] [화학식1129][Formula 1128] [Formula 1128] [Formula 1129]

[화학식1130] [화학식1131] [화학식1132] [화학식1133][Formula 1133] [Formula 1132] [Formula 1133]

[화학식1134] [화학식1135] [화학식1136] [화학식1137][Formula 1137] [Formula 1137]

[화학식1138] [화학식1139] [화학식1140] [화학식1141][Formula 1111] [Formula 1111]

[화학식1142] [화학식1143] [화학식1144] [화학식1145][Formula 1144] [Formula 1144] [Formula 1145]

[화학식1146] [화학식1147] [화학식1148] [화학식1149][Formula 114] [Formula 1144]

[화학식1150] [화학식1151] [화학식1152] [화학식1153][1153] [1153] [1153]

[화학식1154] [화학식1155] [화학식1156] [화학식1157][1157] [1157] [1157]

[화학식1158] [화학식1159] [화학식1160] [화학식1161][Formula 1151] [Formula 1151]

[화학식1162] [화학식1163] [화학식1164] [화학식1165][Formula 1165] [Formula 1165]

[화학식1166] [화학식1167] [화학식1168] [화학식1169][1169] [1169]

[화학식1170] [화학식1171] [화학식1172] [화학식1173][1173] [1172] [1173]

[화학식1174] [화학식1175] [화학식1176] [화학식1177][Chemical Formula 1177] [Chemical Formula 1177]

[화학식1178] [화학식1179] [화학식1180] [화학식1181](1181) [Formula 1181]

[화학식1182] [화학식1183] [화학식1184] [화학식1185][1182] [1183] [1184]

[화학식1186] [화학식1187] [화학식1188] [화학식1189][Formula 1188] [Formula 1188] [Formula 1189]

[화학식1190] [화학식1191] [화학식1192] [화학식1193][Formula 1191] [Formula 1192] [Formula 1193] [Formula 1193]

[화학식1194] [화학식1195] [화학식1196] [화학식1197][Formula 1195] [Formula 1195] [Formula 1197]

[화학식1198] [화학식1199] [화학식1200] [화학식1201][Formula 11] [Formula 11]

[화학식1202] [화학식1203] [화학식1204] [화학식1205][Formula 120] [Formula 1203]

[화학식1206] [화학식1207] [화학식1208] [화학식1209](1209) [Formula 1206]

[화학식1210] [화학식1211] [화학식1212] [화학식1213][Formula 1212] [Formula 1212] [Formula 1212]

[화학식1214] [화학식1215] [화학식1216] [화학식1217][Formula 1214] [Formula 1214]

[화학식1218] [화학식1219] [화학식1220] [화학식1221][Formula 1221] [Formula 1220] [Formula 1221]

[화학식1222] [화학식1223] [화학식1224] [화학식1225][Formula 1222] [Formula 1222] [Formula 1225]

[화학식1226] [화학식1227] [화학식1228] [화학식1229][1229] [1229] [1227]

[화학식1230] [화학식1231] [화학식1232] [화학식1233][Formula 1232] [Formula 1232]

[화학식1234] [화학식1235] [화학식1236] [화학식1237][Formula 1236] [Formula 1236] [Formula 1237]

[화학식1238] [화학식1239] [화학식1240] [화학식1241][1240] [1240]

[화학식1242] [화학식1243] [화학식1244] [화학식1245][1245] [1245] [1245]

[화학식1246] [화학식1247] [화학식1248] [화학식1249][1248] [1248]

[화학식1250] [화학식1251] [화학식1252] [화학식1253][1253] [1251] [1253] [1253]

[화학식1254] [화학식1255] [화학식1256] [화학식1257][1256] [1256] [1257]

[화학식1258] [화학식1259] [화학식1260] [화학식1261][1256] [1256] [1256]

[화학식1262] [화학식1263] [화학식1264] [화학식1265][Formula 1236] [Formula 1236] [Formula 1265]

또한, 본 발명은 애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 개재되며, 상기 [화학식 1]로 표시되는 축합아릴 화합물을 포함하는 층을 구비한 유기전계 발광소자를 제공한다.The present invention also relates to a fuel cell comprising an anode; Cathode; And a layer containing a condensed aryl compound represented by the formula (1), interposed between the anode and the cathode.

이때, 상기 축합아릴 화합물이 함유된 층은 상기 애노드 및 캐소드 사이의 발광층인 것이 바람직하며, 애노드 및 캐소드 사이에는 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함할 수 있다.In this case, the layer containing the condensed aryl compound is preferably a light emitting layer between the anode and the cathode, and a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer And at least one layer selected from the group consisting of

구체적인 예로서, 정공수송층(HTL: Hole Transport Layer)이 추가로 적층되어 있고, 상기 캐소드와 상기 유기발광층 사이에 전자수송층(ETL: Electron Transport Layer)이 추가로 적층되어 있는 것일 수 있는데, 상기 정공수송층은 애노드로부터 정공을 주입하기 쉽게 하기 위하여 적층되는 것으로서, 상기 정공수송층의 재료로는 이온화 포텐셜이 작은 전자공여성 분자가 사용되는데, 주로 트리페닐아민을 기본 골격으로 하는 디아민, 트리아민 또는 테트라아민 유도체가 많이 사용되고 있다.As a specific example, a hole transport layer (HTL) may be additionally stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic emission layer. An electron donor molecule having a low ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative having a basic skeleton of triphenylamine is used as the material of the hole transport layer. It is widely used.

본 발명에서도 상기 정공수송층의 재료로서 당업계에 통상적으로 사용되는 것인 한 특별히 제한되지 않으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(a-NPD) 등을 사용할 수 있다.In the present invention, the material for the hole transport layer is not particularly limited as long as it is commonly used in the art. For example, N, N'-bis (3-methylphenyl) -N, N'- , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (a-NPD).

상기 정공수송층의 하부에는 정공주입층(HIL: Hole Injecting Layer)을 추가적으로 더 적층할 수 있는데, 상기 정공주입층 재료 역시 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있으며, 예를 들어 CuPc(copper phthalocyanine) 또는 스타버스트(Starburst)형 아민류인 TCTA (4,4',4"-tri(N-carbazolyl) triphenyl-amine), m-MTDATA(4,4',4"-tris-(3-methylphenylphenyl amino)triphenylamine) 등을 사용할 수 있다.A HIL (Hole Injection Layer) may be additionally deposited on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenylamino) triphenylamine).

또한, 본 발명에 따른 유기전계발광소자에 사용되는 상기 전자수송층은 캐소드로부터 공급된 전자를 유기발광층으로 원활히 수송하고 상기 유기발광층에서 결합하지 못한 정공의 이동을 억제함으로써 발광층 내에서 재결합할 수 있는 기회를 증가시키는 역할을 한다. 상기 전자수송층 재료로는 당 기술분야에서 통상적으로 사용되는 것이면 특별히 제한되지 않고 사용할 수 있음은 물론이며, 예를 들어 옥사디아졸 유도체인 PBD, BMD, BND 또는 Alq₃ 등을 사용할 수 있다.In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, . The material of the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

한편, 상기 전자수송층의 상부에는 캐소드로부터의 전자 주입을 용이하게 해주어 궁극적으로 파워효율을 개선 시키는 기능을 수행하는 전자주입층(EIL: Electron Injecting Layer)을 더 적층시킬 수도 있는데, 상기 전자주입층 재료 역시 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예를 들어, LiF, NaCl, CsF, Li₂O, BaO 등의 물질을 이용할 수 있다.Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자 등에 사용될 수 있다.The organic electroluminescent device according to the present invention can be used for a display device, a display device, an element for a single color or a white light, and the like.

도 1은 본 발명의 유기전계발광소자의 구조를 나타내는 단면도이다. 본 발명에 따른 유기전계발광소자는 애노드(20), 정공수송층(40), 유기발광층(50), 전자수송층(60) 및 캐소드(80)을 포함하며, 필요에 따라 정공주입층(30)과 전자주입층(70)을 더 포함할 수 있으며, 그 이외에도 1층 또는 2층의 중간층을 더 형성하는 것도 가능하며, 정공저지층 또는 전자저지층을 더 형성시킬 수도 있다.1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic emission layer 50, an electron transport layer 60 and a cathode 80, The electron injecting layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

도 1을 참조하여 본 발명의 유기전계발광소자 및 그 제조방법에 대하여 살펴보면, 다음과 같다. 먼저 기판(10) 상부에 애노드 전극용 물질을 코팅하여 애노드(20)를 형성한다. 여기에서 기판(10)으로는 통상적인 유기 EL 소자에서 사용되는 기판을 사용하는데 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유기 기판 또는 투명 플라스틱 기판이 바람직하다. 그리고, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO₂), 산화아연(ZnO) 등을 사용한다.Referring to FIG. 1, the organic electroluminescent device of the present invention and its manufacturing method will be described as follows. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

상기 애노드(20) 전극 상부에 정공 주입층 물질을 진공열 증착, 또는 스핀 코팅하여 정공주입층(30)을 형성한다. 그 다음으로 상기 정공주입층(30)의 상부에 정공수송층 물질을 진공 열증착 또는 스핀 코팅하여 정공수송층(40)을 형성한다. 이어서, 상기 정공수송층(40)의 상부에 유기발광층(50)을 적층하고 상기 유기발광층(50)의 상부에 선택적으로 정공저지층(미도시)을 진공 증착 방법, 또는 스핀 코팅 방법으로서 박막을 형성할 수 있다. 상기 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO(Highest Occupied Molecular Orbital) 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 이 때, 사용되는 정공 저지 물질은 특별히 제한되지는 않으나 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며 대표적으로 BAlq, BCP, TPBI 등이 사용될 수 있다.A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30. A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

이러한 정공저지층 위에 전자수송층(60)을 진공 증착 방법, 또는 스핀 코팅 방법을 통해 증착한 후에 전자주입층(70)을 형성하고 상기 전자주입층(70)의 상부에 캐소드 형성용 금속을 진공 열증착하여 캐소드(80) 전극을 형성함으로써 유기 EL 소자가 완성된다. 여기에서 캐소드 형성용 금속으로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리듐(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용할 수 있으며, 전면 발광 소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수 있다.After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

또한, 본 발명의 다른 일 실시예에 의하면, 상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성될 수 있으며, 본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자에 사용될 수 있다.
According to another embodiment of the present invention, at least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer is formed by a single molecular deposition method or a solution process And the organic electroluminescent device according to the present invention can be used for a display device, a display device, and a monochromatic or white illumination device.

이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않는다는 것은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.
Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

<실시예><Examples>

합성예 1. [화학식 52]의 합성Synthesis Example 1. Synthesis of [Formula 52]

1-(1) 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌의 합성1- (1) Synthesis of 2-bromo-7- (4-bromo-2-nitrophenyl) -9,9-diphenyl-9H-

1 L 둥근바닥플라스크에 2-브로모-9,9-다이페닐-9H-플루오렌-7-보론산 21.0 g (48 mmol), 2,5-다이브로모나이트로벤젠 16 g(57 mmol), 탄산칼슘 13.2 g(95 mmol), 테트라하이드로퓨란 126 mL, 다이옥산 42 mL, 물 126 mL를 넣고 교반하였다. 질소 분위기에서 반응액에 테트라키스(트리페닐포스핀)팔라듐(0) 1.1 g(1 mmol)을 넣고 환류시켰다. 반응 종료 후 상온으로 냉각시켰다. 냉각 후 EA/H2O로 추출하고 유기층을 모아 농축한뒤 컬럼 분리하였다. 분리액을 MC/MeOH로 재결정하고 결정을 감압하여 건조하였다.(9.1 g, 32%)
To a 1 L round bottom flask was added 21.0 g (48 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene-7-boronic acid, 16 g (57 mmol) 13.2 g (95 mmol) of calcium carbonate, 126 mL of tetrahydrofuran, 42 mL of dioxane and 126 mL of water were added and stirred. 1.1 g (1 mmol) of tetrakis (triphenylphosphine) palladium (0) was added to the reaction solution in a nitrogen atmosphere and refluxed. After completion of the reaction, the reaction mixture was cooled to room temperature. After cooling, the mixture was extracted with EA / H2O and the organic layer was collected, concentrated, and then subjected to column separation. The separated solution was recrystallized from MC / MeOH and the crystals were dried under reduced pressure (9.1 g, 32%).

1-(2) 5-브로모-2-(7-브로모-9,9-다이페닐-9H-플루오렌-2-yl)아닐린의 합성1- (2) Synthesis of 5-bromo-2- (7-bromo-9,9-diphenyl-9H-fluoren-2-yl) aniline

2 L 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌 9.1 g(15 mmol), 에탄올 182 mL, 염산 220 mL를 넣고 온도를 0 ℃ 이하로 냉각한 다음 틴 파우더 4.5 g(38 mmol)을 조금씩 넣은 후 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌이 완전히 녹을 때까지 가열하고 TLC로 반응 종료를 확인하고 40% 수산화나트륨 용액을 넣어 PH 10 이상으로 만들고 EA/H2O로 추출한 뒤 유기층을 취해 농축하고 MeOH로 재결정하고 결정을 감압 건조하였다(5.5 g, 63.6%)
To a 2 L round bottom flask was added 9.1 g (15 mmol) of 2-bromo-7- (4-bromo-2-nitrophenyl) -9,9- diphenyl-9H-fluorene, 182 mL of ethanol, mL, and the temperature was lowered to 0 ° C or lower. 4.5 g (38 mmol) of tin powder was added in small portions, and 2-bromo-7- (4-bromo-2-nitrophenyl) -9H-fluorene was heated until complete dissolution. After confirming the completion of the reaction by TLC, 40% sodium hydroxide solution was added to make PH 10 or higher. The solution was extracted with EA / H 2 O. The organic layer was collected and concentrated, recrystallized with MeOH, (5.5 g, 63.6%).

1-(3) 2-브로모-7-(4-브로모-2-아이오도페닐)-9,9-다이페닐-9H-플루오렌의 합성1- (3) Synthesis of 2-bromo-7- (4-bromo-2-iodophenyl) -9,9-diphenyl-9H-

250 mL 둥근바닥플라스크에 5-브로모-2-(7-브로모-9,9-다이페닐-9H-플루오렌-2-yl)아닐린 5.5 g(10 mmol), 소듐나이트라이트 1.7 g(24 mmol), 포타슘 아이오다이드 4.02 g(24.2 mmol)을 넣고 교반하면서 온도를 0 ℃ 이하로 내리고 염산을 천천히 떨어뜨린 후 반응을 종료하고 온도를 상온으로 올리고 물을 넣고 교반한 다음 다이메틸클로라이드(MC)를 넣고 교반해준 뒤 소듐 사이오설페이트를 반응액이 노란색으로 될 때까지 첨가해주고 MC/H2O로 추출하고 유기층을 농축해 컬럼 분리하고 분리액을 농축해 헥산으로 재결정하고 생성된 결정을 감압 건조하였다.(5 g, 76%)
5.5 g (10 mmol) of 5-bromo-2- (7-bromo-9,9-diphenyl-9H-fluoren-2-yl) aniline, 1.7 g (24 mmol) of sodium nitrite in a 250 mL round bottom flask and 4.02 g (24.2 mmol) of potassium iodide were added, the temperature was lowered to 0 ° C with stirring, the hydrochloric acid was slowly dropped, the reaction was terminated, the temperature was raised to room temperature, water was added thereto and the mixture was stirred with dimethyl chloride ), And the mixture was stirred. Then, sodium cyan sulfate was added until the reaction solution became yellow, and the mixture was extracted with MC / H2O. The organic layer was concentrated and the column was separated. The separated solution was concentrated and recrystallized with hexane. (5 g, 76%).

1-(4) 2-브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌 의 합성Synthesis of 2-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) -9,9-diphenyl-9H-

100 mL 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-아이오도페닐)-9,9-다이페닐-9H-플루오렌 5 g(7 mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 0.2 g(0.15 mmol), 코퍼(I)아이오다이드 0.1 g(0.36 mmol), 트리에틸아민 200 mL를 넣고 상온에서 서서히 교반하면서 페닐아세틸렌 0.8 mL(7 mmol)을 천천히 떨어뜨렸다. 약 1 시간 동안 교반하고 헥산을 부어 반응을 종료하였다. 반응액을 농축해서 컬럼 분리하고 분리액을 농축한 뒤 재결정하고 결정을 감압 건조하였다.(3.8 g, 79.3%)
To a 100 mL round bottom flask was added 5 g (7 mmol) of 2-bromo-7- (4-bromo-2-iodophenyl) -9,9- Pyridine 0.1 g (0.36 mmol) of copper (I) iodide and 200 mL of triethylamine were slowly added dropwise slowly to 0.8 mL (7 mmol) of phenylacetylene while slowly stirring at room temperature I dropped it. Stir for about 1 hour and pour hexane to terminate the reaction. The reaction solution was concentrated to separate the column. The separated solution was concentrated, and then recrystallized. The crystals were dried under reduced pressure (3.8 g, 79.3%).

1-(5) 3,10-다이브로모-6,12,12-트리페닐-12H-인데노[1,2-b]페난스렌의 합성Synthesis of 1- (5) 3,10-dibromo-6,12,12-triphenyl-12H-indeno [1,2-b] phenanthrene

500 mL 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌 3.8 g(6 mmol), 아이론(III)트라이플루오로메탄설포네이트 0.3 g(1 mmol), 1,2-다이클로로에탄 300 mL를 넣고 24 시간 동안 환류시켰다. 반응종료 후 반응액을 식히고 컬럼 분리하고 분리액을 농축해 MC/MeOH로 재결정하고, 생성된 결정을 여과해서 건조하였다.(3.4 g, 89.5%)
To a 500 mL round bottom flask was added 3.8 g (6 mmol) of 2-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) -9,9- ) 0.3 g (1 mmol) of trifluoromethanesulfonate and 300 mL of 1,2-dichloroethane were added, and the mixture was refluxed for 24 hours. After the completion of the reaction, the reaction solution was cooled, the reaction mixture was separated, and the separated solution was concentrated and recrystallized from MC / MeOH. The resulting crystals were filtered and dried (3.4 g, 89.5%

1-(6) [화학식 52]의 합성1- (6) Synthesis of [Formula 52]

250 mL 둥근바닥 플라스크에 3,10-다이브로모-6,12,12-트리페닐-12H-인데노[1,2-b]페난스렌 3.4 g(5 mmol), bis(4-tert-부틸페닐)아닐린 3.5 g(13 mmol), 팔라듐(II)아세테이트 0.05 g(0.2 mmol), 소듐-t-부톡사이드 2.0 g(21 mmol), 톨루엔 50 mL를 넣고 교반하면서 가열하였다. 온도가 60 ℃가 되면 트리-t-부틸포스핀 을 넣고 온도를 더 높여 환류시켰다. 반응이 종료되면 반응액을 식히고 컬럼 분리하였다. 분리액을 농축해 재결정하고 결정을 테트라하이드로퓨란에 녹여 아세톤으로 다시 재결정하였다. 같은 방법으로 6 회 이상 재결정하였다.(2.6 g, 47.4%)
To a 250 mL round bottom flask was added 3.4 g (5 mmol) of 3,10-dibromo-6,12,12-triphenyl-12H-indeno [1,2- b] phenanthrene, bis (4- ) 3.5 g (13 mmol) of aniline, 0.05 g (0.2 mmol) of palladium (II) acetate, 2.0 g (21 mmol) of sodium t-butoxide and 50 mL of toluene were placed and heated with stirring. When the temperature reached 60 ° C, tri-t-butylphosphine was added and the temperature was further raised to reflux. When the reaction was completed, the reaction solution was cooled and the column was separated. The separated solution was concentrated and recrystallized. The crystals were dissolved in tetrahydrofuran and recrystallized again with acetone. The same procedure was repeated six times or more (2.6 g, 47.4%).

합성예 2. [화학식 64]의 합성Synthesis Example 2. Synthesis of [Formula 64]

1-(7)1- (7)

상기 [화학식 52]의 합성방법과 동일한 방법으로 bis(4-tert-부틸페닐)아닐린 대신 4-tert-부틸-N-p-(페닐-D5)아닐린 2.9 g(13 mmol)을 사용해 [화학식 64] 를 합성하였다. (2.3 g, 46.4%)
(4-tert-butyl-Np- (phenyl-D5) aniline (2.9 g, 13 mmol) was used in the same manner as in the synthesis of the compound of the above Formula 52, instead of bis Were synthesized. (2.3 g, 46.4%).

합성예 3. [화학식 101]의 합성Synthesis Example 3. Synthesis of [Formula 101]

2-(1) 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌 의 합성2- (1) Synthesis of 2-bromo-7- (4-bromo-2-nitrophenyl) -9,9-diphenyl-9H-

1 L 둥근바닥플라스크에 2-브로모-9,9-다이페닐-9H-플루오렌-7-보론산21.0 g(48 mmol), 2,5-다이브로모나이트로벤젠 16 g(57 mmol), 탄산칼슘 13.2 g(95 mmol), 테트라하이드로퓨란 126 mL, 다이옥산 42 mL, 물 126 mL를 넣고 교반하였다. 질소 분위기에서 반응액에 테트라키스(트리페닐포스핀)팔라듐(0) 1.1 g(1 mmol)을 넣고 환류시켰다. 반응 종료 후 상온으로 냉각시켰다. 냉각 후 EA/H2O로 추출하고 유기층을 모아 농축한 뒤 컬럼 분리하였다. 분리액을 MeOH로 재결정하고 결정을 감압하여 건조하였다.(9.1 g, 32%)
To a 1 L round bottom flask was added 21.0 g (48 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene-7-boronic acid, 16 g (57 mmol) 13.2 g (95 mmol) of calcium carbonate, 126 mL of tetrahydrofuran, 42 mL of dioxane and 126 mL of water were added and stirred. 1.1 g (1 mmol) of tetrakis (triphenylphosphine) palladium (0) was added to the reaction solution in a nitrogen atmosphere and refluxed. After completion of the reaction, the reaction mixture was cooled to room temperature. After cooling, the mixture was extracted with EA / H2O and the organic layer was collected, concentrated, and then subjected to column separation. The separated solution was recrystallized with MeOH, and the crystals were dried under reduced pressure (9.1 g, 32%).

2-(2) 5-브로모-2-(7-브로모-9,9-다이페닐-9H-플루오렌-2-yl)아닐린의 합성2- (2) Synthesis of 5-bromo-2- (7-bromo-9,9-diphenyl-9H-fluoren-

2 L 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌 9.1 g(15 mmol) 에탄올 182 mL, 염산 220 mL를 넣고 온도를 0 ℃ 이하로 냉각한 다음 틴 파우더 4.5 g(38 mmol)을 조금씩 넣은 후 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌이 완전히 녹을 때까지 가열하고 반응이 종결되면 40% 수산화나트륨 용액을 넣어 PH 10 이상으로 만들고 EA/H2O로 추출한 뒤 유기층을 취해 농축하고 MeOH로 재결정하고 결정을 감압 건조하였다.(5.5 g, 63.6%)
9.1 g (15 mmol) of 2-bromo-7- (4-bromo-2-nitrophenyl) -9,9-diphenyl-9H-fluorene was added to a 2 L round bottom flask, Cooled to below 0 ° C, and then 4.5 g (38 mmol) of tin powder was added in small portions. Then, 2-bromo-7- (4-bromo-2-nitrophenyl) After 9H-fluorene was completely dissolved, 40% sodium hydroxide solution was added to make PH 10 or higher. After extraction with EA / H 2 O, the organic layer was collected, concentrated, recrystallized with MeOH, and dried under reduced pressure (5.5 g, 63.6%)

2-(3) 2-브로모-7-(4-브로모-2-아이오도페닐)-9,9-다이페닐-9H-플루오렌 의 합성2- (3) Synthesis of 2-bromo-7- (4-bromo-2-iodophenyl) -9,9-diphenyl-9H-

250 mL 둥근바닥플라스크에 5-브로모-2-(7-브로모-9,9-다이페닐-9H-플루오렌-2-yl)아닐린 5.5 g(10 mmol), 소듐나이트라이트 1.7 g(24 mmol), 포타슘 아이오다이드 4.02 g(24.2 mmol)을 넣고 교반하면서 온도를 0 ℃ 이하로 내리고 염산을 천천히 떨어뜨린 후 반응을 종료하고 온도를 상온으로 올리고 물을 넣고 교반하였다. 다이메틸클로라이드(MC)를 넣고 교반해준 뒤 소듐 사이오설페이트를 반응액이 노란색으로 될 때까지 첨가해주고 MC/H2O로 추출하고 유기층을 농축해 컬럼 분리 하고 분리액을 농축해 헥산으로 재결정하고 생성된 결정을 감압 건조하였다.(5 g, 76%)
5.5 g (10 mmol) of 5-bromo-2- (7-bromo-9,9-diphenyl-9H-fluoren-2-yl) aniline, 1.7 g (24 mmol) of sodium nitrite in a 250 mL round bottom flask mmol) and 4.02 g (24.2 mmol) of potassium iodide were added, the temperature was lowered to 0 ° C with stirring, the hydrochloric acid was slowly dropped, the reaction was terminated, the temperature was raised to room temperature, water was added and stirred. After adding dimethyl chloride (MC) and stirring, sodium cyan sulfate was added until the reaction solution turned yellow and extracted with MC / H2O. The organic layer was concentrated to separate the column, and the separated solution was concentrated and recrystallized from hexane The crystals were dried under reduced pressure (5 g, 76%).

2-(4) 2-브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌의 합성2- (4) Synthesis of 2-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) -9,9-diphenyl-9H-

2-(5) 7-(4-(다이페닐아미노)-2-(페닐에티닐)페닐)-N,N,9,9-테트라페닐-9H-플루오렌-2-아민의 합성Synthesis of 7- (4- (diphenylamino) -2- (phenylethynyl) phenyl) -N, N, 9,9-tetraphenyl-9H-fluoren-

250 mL 둥근바닥플라스크에 브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌 3.4 g(5 mmol), 다이페닐아민 2.1 g(13 mmol), 팔라듐(II)아세테이트 0.05 g(0.2 mmol), 소듐-t-부톡사이드 2.0 g(21 mmol), 톨루엔 50 mL를 넣고 가열해서 약 60 ℃가 되면 트리부틸포스핀을 넣고 환류시켰다. 반응을 종료하고 반응액을 상온으로 식히고 컬럼 분리하고 분리액을 농축해 재결정하고 결정을 건조하였다.(2.6 g, 60.2%)
To a 250 mL round bottom flask was added 3.4 g (5 mmol) of bromo-7- (4-bromo-2- (phenylethynyl) phenyl) -9,9- 0.05 g (0.2 mmol) of palladium (II) acetate, 2.0 g (21 mmol) of sodium-t-butoxide and 50 mL of toluene were charged and heated to about 60 DEG C, and tributylphosphine was added thereto and refluxed . After completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting mixture was subjected to column separation. The separated mixture was concentrated to give crystals. The crystals were dried (2.6 g, 60.2%

2-(6) 5-아이오도-N3,N3,N10,N10,6,12,12-헵타페닐-12H-인데노[1,2-b]페난스렌-3,10-다이아민의 합성Synthesis of 5-iodo-N3, N3, N10, N10,6,12,12-heptaphenyl-12H-indeno [l, 2-b] phenanthrene-3,10-diamine

250 mL 둥근바닥플라스크에 7-(4-(다이페닐아미노)-2-(페닐에티닐)페닐)-N,N,9,9-테트라페닐-9H-플루오렌-2-아민 2.6 g(3 mmol)을 MC에 녹여 -78 ℃로 냉각하고 아이오딘모노클로라이드 4 mL를 천천히 떨어뜨렸다. 동일한 온도에서 1 시간 동안 교반하고 온도를 상온으로 올린 후 소듐바이설파이트 포화용액을 넣어 반응을 종료시키고 MC/H2O로 추출한 다음 유기층을 농축해서 결정을 석출하고 MeOH 슬러리 후 여과하고 건조하였다.(2.4 g, 92%)
To a 250 mL round-bottomed flask was added 2.6 g (3 < RTI ID = 0.0 > (4- (diphenylamino) -2- (phenylethynyl) phenyl) -N, N, 9,9-tetraphenyl-9H- mmol) was dissolved in MC, cooled to -78 ° C and 4 mL of iodine monochloride was slowly dropped. After stirring at the same temperature for 1 hour, the temperature was raised to room temperature, and the reaction was terminated by adding a saturated sodium bisulfite solution. The reaction mixture was extracted with MC / H 2 O and the organic layer was concentrated to precipitate crystals. g, 92%)

2-(7) [화학식 101]의 합성2- (7) Synthesis of [Formula 101]

250 mL 둥근바닥플라스크에 5-아이오도-N3,N3,N10,N10,6,12,12-헵타페닐-12H-인데노[1,2-b]페난스렌-3,10-다이아민 2.4 g(3 mmol), 페닐보론산 0.4 g (3 mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 0.1 g(0.1 mmol), 포타슘카보네이트 0.7 g(5 mmol), 테트라하이드로퓨란 14.4 mL, 다이옥산 4.8 mL, 물 14.4 mL를 넣고 온도를 올려 환류하면서 24 시간 반응시켰다. 반응이 종결된후 EA/H2O로 추출하고 유기층을 모아 농축하였다. 농축액을 컬럼 분리하고 분리액을 농축해 재결정하고 결정을 건조하였다. (1.8 g, 79.1%)
A 250 mL round bottom flask was charged with 2.4 g of 5-iodo-N3, N3, N10, N10,6,12,12-heptaphenyl-12H-indeno [ 0.1 g (0.1 mmol) of tetrakis (triphenylphosphine) palladium (0), 0.7 g (5 mmol) of potassium carbonate, 14.4 mL of tetrahydrofuran, 4.8 mL of water and 14.4 mL of water, and the mixture was heated at reflux for 24 hours. After the reaction was completed, the mixture was extracted with EA / H2O, and the organic layer was collected and concentrated. The concentrate was subjected to column separation, the separated solution was concentrated, and recrystallized, and the crystals were dried. (1.8 g, 79.1%).

합성예 4. [화학식 105]의 합성Synthesis Example 4. Synthesis of [Formula 105]

2-(8)2- (8)

상기 합성예 2-(4)에서 합성한 2-브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌를 사용해 다이페닐아민 대신 4-(나프탈렌-1-yl-아미노)벤조나이트라일을 사용해 상기와 같은 방법으로 합성하였다.(1.5 g, 65.4%)
(4-bromo-2- (phenylethynyl) phenyl) -9,9-diphenyl-9H-fluorene synthesized in Synthesis Example 2- (4) was used instead of diphenylamine (1.5 g, 65.4%) was obtained using 4- (naphthalen-1-yl-amino) benzonitrile.

합성예 5. [화학식 851]의 합성Synthesis Example 5. Synthesis of [Formula 851]

3-(1) 2-(7-브로모페난스렌-2-yl)-4,4,5,5-테트라메틸-1,3,2-다이옥사보로렌의 합성3- (1) Synthesis of 2- (7-bromophenanthrene-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolene

1 L 둥근바닥 플라스크에 2,7-다이브로모페난스렌 22 g(65 mmol), Bis(피나콜라토)다이보론 18.8 g(74 mmol), PdCl2(dppf) 1.6 g(2 mmol), 포타슘아세테이트 20.6 g(210 mmol), 톨루엔 440 mL를 넣고 110 ℃ 정도로 가열해 환류시켰다. 반응이 종료되면 뷰흐너 깔때기에 셀라이트와 실리카겔을 깔고 뜨거운 톨루엔을 이용해 여과하였다. 여액을 농축하고 컬럼 분리한 후 분리액을 농축해 재결정하고 생성된 결정을 건조하였다.(18 g, 71.8%)
To a 1 L round bottom flask was added 22 g (65 mmol) of 2,7-dibromophenanthrene, 18.8 g (74 mmol) Bis (pinacolato) diboron, 1.6 g (2 mmol) PdCl2 g (210 mmol) and toluene (440 mL) were added, and the mixture was heated to about 110 DEG C and refluxed. When the reaction was completed, celite and silica gel were placed on a Buchner funnel and filtered using hot toluene. The filtrate was concentrated and the column was separated. The separated solution was concentrated and recrystallized, and the resulting crystals were dried (18 g, 71.8%).

3-(2) 2-브로모-7-(4-브로모-2-나이트로페닐)페난스렌의 합성3- (2) Synthesis of 2-bromo-7- (4-bromo-2-nitrophenyl) phenanthrene

1 L 둥근바닥플라스크에2-(7-브로모페난스렌-2-yl)-4,4,5,5-테트라메틸-1,3,2-다이옥사보로렌 18 g(47 mmol), 2,5-다이브로모나이트로벤젠 14.5 g(52 mmol), PdCl2(dppf) 0.8 g(1 mmol), 소듐바이카보네이트 7.9 g(94 mmol), 테트라하이드로퓨란 360 mL, 물 180 mL를 넣고 환류하면서 반응시켰다. 반응이 종결되면 상온으로 냉각하고 EA/H2O로 추출해 유기층을 농축해서 컬럼 분리하였다. 분리액을 농축하고 재결정을 하고 생성된 결정을 여과해서 건조하였다.(14.3 g, 66.6%)
18 g (47 mmol) of 2- (7-bromophenanthren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added to a 1 L round bottom flask, Dibromonitrobenzene 14.5 g (52 mmol) of benzene, 0.8 g (1 mmol) of PdCl2 (dppf), 7.9 g (94 mmol) of sodium bicarbonate, 360 mL of tetrahydrofuran and 180 mL of water were added and reacted under reflux . When the reaction was completed, the reaction mixture was cooled to room temperature, extracted with EA / H2O, and the organic layer was concentrated to separate the column. The separated solution was concentrated, recrystallized, and the resulting crystals were filtered and dried (14.3 g, 66.6%).

3-(3) 3,10-다이브로모-12H-나프토[1,2-b]카바졸의 합성3- (3) Synthesis of 3,10-dibromo-12H-naphtho [1,2-b] carbazole

500 mL 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-나이트로페닐)페난스렌 14.3 g(31 mmol), 트리페닐포스핀 20.5 g(78 mmol), 다이클로로벤젠 286 mL를 넣고 환류시켰다. 반응이 종결되면 뷰흐너 깔때기에 셀라이트와 실리카겔을 깔고 뜨거운 다이클로로벤젠을 이용해 여과하였다. 여액을 농축하고 재결정해서 생성된 결정을 건조하였다.(9.5 g, 71.6%)
To a 500 mL round bottom flask was added 14.3 g (31 mmol) of 2-bromo-7- (4-bromo-2-nitrophenyl) phenanthrene, 20.5 g (78 mmol) of triphenylphosphine, 286 mL And the mixture was refluxed. When the reaction was complete, celite and silica gel were placed on a Buchner funnel and filtered using hot dichlorobenzene. The filtrate was concentrated and recrystallized to give crystals which were dried (9.5 g, 71.6%).

3-(4) 3,10-다이브로모-12-페닐-12H-나프토[1,2-b]카바졸의 합성3- (4) Synthesis of 3,10-dibromo-12-phenyl-12H-naphtho [1,2-b]

250 mL 둥근바닥플라스크에 3,10-다이브로모-12H-나프토[1,2-b]카바졸 9.5 g(22 mmol), 아이오도벤젠 6.4 g(31 mmol), 코퍼파우더 2.14 g(33.6 mmol), 포타슘카보네이트 4.3 g(31 mmol), 18-크라운-6 1.78 g(6.7 mmol), 다이메틸설폭사이드 150 mL를 넣고 24 시간 동안 환류시켰다. 반응이 종결되면 MC/H2O로 추출하고 유기층을 모아 농축한 후 컬럼 분리하고 분리액을 농축하였다. (8.6 g, 76.6%)
To a 250 mL round bottom flask was added 9.5 g (22 mmol) of 3,10-dibromo-12H-naphtho [1,2-b] carbazole, 6.4 g (31 mmol) of iodobenzene, 2.14 g ), Potassium carbonate (4.3 g, 31 mmol), 18-crown-6 (1.78 g, 6.7 mmol) and dimethylsulfoxide (150 mL) were added and refluxed for 24 hours. When the reaction was completed, the reaction mixture was extracted with MC / H 2 O. The organic layer was collected, concentrated, and then the column was separated and the separated solution was concentrated. (8.6 g, 76.6%).

3-(5) [화학식 843]의 합성3- (5) Synthesis of [Formula 843]

250 mL 둥근바닥플라스크에 3,10-다이브로모-12-페닐-12H-나프토[1,2-b]카바졸 8.6 g(17 mmol), N-(4-플루오로페닐)나프탈렌-2-아민 9.8 g(41 mmol), 팔라듐(II)아세테이트 0.15 g(0.7 mmol), 소듐-t-부톡사이드 6.6 g(69 mmol), 톨루엔100 mL를 넣고 가열하면서 교반하고 60 ℃가 되면 트리-t-부틸포스핀 1.1 mL(2.7 mmol)을 넣어주고 환류시켰다. 반응이 종결되면 상온으로 식히고 농축한 다음 컬럼 분리하고 분리액을 농축해 MeOH로 재결정하고 생성된 결정을 건조하였다. (6.8 g, 48.7%)
To a 250 mL round bottom flask was added 8.6 g (17 mmol) of 3,10-dibromo-12-phenyl-12H-naphtho [1,2- b] carbazole, N- (4- fluorophenyl) The mixture was stirred while heating with 9.8 g (41 mmol) of amine, 0.15 g (0.7 mmol) of palladium (II) acetate, 6.6 g (69 mmol) of sodium t-butoxide and 100 mL of toluene, 1.1 mL (2.7 mmol) of butylphosphine was added and refluxed. After the reaction was completed, the reaction mixture was cooled to room temperature, concentrated, and then subjected to column separation. The separated solution was concentrated, recrystallized from MeOH, and dried. (6.8 g, 48.7%).

3-(6) [화학식 851]의 합성3- (6) Synthesis of [Formula 851]

상기 합성예 3-(4)에서 합성한 3,10-다이브로모-12-페닐-12H-나프토[1,2-b]카바졸을 사용하고 N-(4-플루오로페닐)나프탈렌-2-아민 대신 다이페닐아민을 사용해 상기와 같은 방법으로 합성하였다.(5.8 g, 49.9%)
Using the 3,10-dibromo-12-phenyl-12H-naphtho [1,2-b] carbazole synthesized in the above Synthesis Example 3- (4), N- (4-fluorophenyl) naphthalene- (5.8 g, 49.9%). &Lt; RTI ID = 0.0 >

합성예 6. Synthesis Example 6

4-(1) 7-브로모다이벤조[b,d]사이오펜-3-yl보론산의 합성4- (1) Synthesis of 7-bromodibenzo [b, d] thiophen-3-ylboronic acid

2 L 둥근바닥 플라스크에 3,7-다이브로모벤조[b,d]사이오펜 50 g(146 mmol), 테트라하이드로퓨란 400 mL를 넣고 질소분위기에서 드라이아이스와 아세톤으로 -78 ℃로 냉각하였다. 온도를 유지하면서 1.6 M 부틸리튬 100.5 mL를 천천히 떨어뜨리고 나서 온도를 유지하면서 2 시간 동안 교반하였다. 동일한 온도에서 트리메틸보레이트 103 mL를 천천히 떨어뜨리고 나서 온도를 상온으로 올리고 24 시간 교반하였다. 반응이 종결된 후 2 N 염산을 넣고 교반하였다. 반응액에 EA를 넣어서 교반하고 EA/H2O로 추출한 후 EA층을 PH 6~7까지 중화하였다. 유기층을 농축하고 EA:Hexane=1:4 용액과 글래스필터로 불순물을 제거하고 EA:MEOH=10:1 용액으로 Main을 분리한다. 분리액을 농축하고 헥산으로 재결정하고, 생성된 결정을 건조하였다.(29.4 g, 65.5%)
50 g (146 mmol) of 3,7-dibromobenzo [b, d] thiophene and 400 mL of tetrahydrofuran were placed in a 2 L round bottom flask and cooled to -78 ° C with dry ice and acetone in a nitrogen atmosphere. 100.5 mL of 1.6 M butyllithium was slowly dropped while maintaining the temperature, followed by stirring for 2 hours while maintaining the temperature. Trimethylborate (103 mL) was slowly dropped at the same temperature, then the temperature was raised to room temperature and stirred for 24 hours. After the reaction was completed, 2 N hydrochloric acid was added and stirred. EA was added to the reaction solution, stirred, and extracted with EA / H2O. Then, the EA layer was neutralized to PH 6 to 7. The organic layer was concentrated, the impurities were removed with a solution of EA: Hexane = 1: 4 and a glass filter, and the main was separated with a solution of EA: MeOH = 10: 1. The separated solution was concentrated, recrystallized with hexane, and the resulting crystals were dried (29.4 g, 65.5%).

4-(2) 3-브로모-7-(4-브로모-2-나이트로페닐)다이벤조[b,d]사이오펜의 합성4- (2) Synthesis of 3-bromo-7- (4-bromo-2-nitrophenyl) dibenzo [b, d]

1 L 둥근바닥플라스크 에 3-브로모-7-(4-브로모-2-나이트로페닐)다이벤조[b,d]사이오펜 29.4 g(96 mmol), 2,5-다이브로모나이트로벤젠 32.3 g(115 mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 2.2 g(1.9 mmol), 탄산칼륨 26.5 g(192 mmol), 테트라하이드로퓨란 176.4 mL, 다이옥산 58.8 mL, 물 176.4 mL를 넣고 환류시켰다. 반응을 종결하고 상온으로 식히고 EA/H2O로 추출하고 유기층을 농축한 다음 컬럼 분리하였다. 분리액을 농축하고 MeOH로 재결정하고 생성된 결정을 건조하였다.(28 g, 63.1%)
A 1 L round bottom flask was charged with 29.4 g (96 mmol) of 3-bromo-7- (4-bromo-2-nitrophenyl) dibenzo [b, 2.2 g (1.9 mmol) of tetrakis (triphenylphosphine) palladium (0), 26.5 g (192 mmol) of potassium carbonate, 176.4 mL of tetrahydrofuran, 58.8 mL of dioxane and 176.4 mL of water were added Lt; / RTI > After completion of the reaction, the mixture was cooled to room temperature, extracted with EA / H2O, and the organic layer was concentrated and then subjected to column separation. The separated solution was concentrated, recrystallized with MeOH, and the resulting crystals were dried (28 g, 63.1%).

4-(3) 5-브로모-2-(7-브로모다이벤조[b,d]사이오펜-3-yl)아닐린의 합성4- (3) Synthesis of 5-bromo-2- (7-bromodibenzo [b, d] thiophen-3-yl) aniline

1 L 둥근바닥플라스크에 3-브로모-7-(4-브로모-2-나이트로페닐)다이벤조[b,d]사이오펜 28 g(60 mmol), 염산 170 mL, 에탄올 560 mL를 넣고 온도를 0 ℃ 이하로 내린 후 틴 파우더 17.9 g(151 mmol)를 조금씩 넣어주고 3-브로모-7-(4-브로모-2-나이트로페닐)다이벤조[b,d]사이오펜이 완전히 녹을 때까지 가열하였다. 반응이 종결되면 상온으로 식히고 40% 수산화나트륨 수용액을 넣어 PH 10 이상으로 만들었다. EA/H2O로 추출하고 유기층을 취해 농축하고 MeOH로 재결정하고 생성된 결정을 건조하였다.(23 g, 87.8%)
28 g (60 mmol) of 3-bromo-7- (4-bromo-2-nitrophenyl) dibenzo [b, d] thiophene, 170 mL of hydrochloric acid and 560 mL of ethanol were placed in a 1 L round bottom flask After the temperature was lowered to 0 ° C, 17.9 g (151 mmol) of tin powder was added little by little and 3-bromo-7- (4-bromo-2-nitrophenyl) dibenzo [b, It was heated until it melted. After the reaction was completed, the reaction mixture was cooled to room temperature and an aqueous solution of 40% sodium hydroxide was added thereto to obtain a pH of 10 or higher. Extraction with EA / H2O, concentration of the organic layer, recrystallization from MeOH and drying of the resulting crystals (23 g, 87.8%).

4-(4) 3-브로모-7-(4-브로모-2-아이오도페닐)다이벤조[b,d]사이오펜의 합성4- (4) Synthesis of 3-bromo-7- (4-bromo-2-iodophenyl) dibenzo [b,

1 L 둥근바닥플라스크에 5-브로모-2-(7-브로모다이벤조[b,d]사이오펜-3-yl)아닐린 23 g(53 mmol), 소듐나이트라이트 9.2 g(133 mmol), 포타슘아이오다이드 22 g(132.7 mmol), 아세토나이트라일 228 mL를 넣고 교반하면서 온도를 0 ℃ 이하로 냉각하고 염산을 천천히 떨어뜨렸다. 반응이 종결되면 온도를 상온으로 올리고 물을 넣고 교반하고 추가로 MC를 넣어서 교반하였다. 소듐사이오설페이트를 반응액이 노란색이 될 때까지 넣어주었다. MC/H2O로 추출하고 MC층을 모아 농축한 후 컬럼 분리하고 분리액을 농축해 헥산으로 재결정하고 생성된 결정을 건조하였다.(25 g, 86.6%)
23 g (53 mmol) of 5-bromo-2- (7-bromodibenzo [b, d] thiophen-3-yl) aniline, 9.2 g (133 mmol) of sodium nitrite, 22 g (132.7 mmol) of iodide and 228 mL of acetonitrile were added, the temperature was lowered to 0 캜 while stirring, and the hydrochloric acid was slowly dropped. When the reaction was completed, the temperature was raised to room temperature, water was added thereto, stirred, and further stirred with MC. Sodium cyanosulfate was added until the reaction solution became yellow. The mixture was extracted with MC / H2O, and the MC layer was collected, concentrated, and then subjected to column separation. The separated solution was concentrated, recrystallized with hexane, and dried (25 g, 86.6%

4-(5) 3-브로모-7-(4-브로모-2-(페닐에티닐)페닐)다이벤조[b,d]사이오펜의 합성4- (5) Synthesis of 3-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) dibenzo [b,

500 mL 둥근바닥플라스크에 3-브로모-7-(4-브로모-2-아이오도페닐)다이벤조[b,d]사이오펜 25 g(46 mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 1.1 g(1 mmol), 요오드화구리 0.4 g(2 mmol), 트리에틸아민 200 mL를 넣고 상온에서 교반g하였다. 서서히 교반하면서 페닐아세틸렌 4.7 mL(46 mmol)을 천천히 떨어뜨렸다. 1시간 동안 교반하고 헥산을 부어 반응을 종결하였다. 반응액을 농축하고 컬럼분리 하고 분리액을 농축해서 재결정하였다. 생성된 결정을 여과해서 건조하였다. (19 g, 79.7%)
To a 500 mL round bottom flask was added 25 g (46 mmol) of 3-bromo-7- (4-bromo-2-iodophenyl) dibenzo [b, d] thiophene, tetrakis (triphenylphosphine) palladium (0) (1.1 g, 1 mmol), copper iodide (0.4 g, 2 mmol) and triethylamine (200 mL) were added and stirred at room temperature. 4.7 mL (46 mmol) of phenylacetylene was slowly dropped while slowly stirring. Stirred for 1 hour and poured into hexane to terminate the reaction. The reaction solution was concentrated, the separated column was separated, and the separated solution was concentrated and recrystallized. The resulting crystals were filtered and dried. (19 g, 79.7%).

4-(6) 3,10-다이브로모-6-페닐벤조[d]페난스로[3,2-b]사이오펜의 합성Synthesis of 4- (6) 3,10-dibromo-6-phenylbenzo [d] phenanthro [3,2-b]

500 mL 둥근바닥플라스크에 3-브로모-7-(4-브로모-2-(페닐에티닐)페닐)다이벤조[b,d]사이오펜 19 g(37 mmol), 아이론(III) 트리플루오로메탄설포네이트 1.8 g(4 mmol), 1,2-다이클로로에탄 300 mL를 넣고 24 시간 동안 환류시켰다. 반응이 종결되면 상온으로 식히고 농축한 뒤 컬럼분리하고 분리액을 농축해서 MeOH로 재결정하고 생성된 결정을 건조하였다.(17 g, 89.5%)
To a 500 mL round bottom flask was added 19 g (37 mmol) of 3-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) dibenzo [b, 1.8 g (4 mmol) of lomethanesulfonate and 300 mL of 1,2-dichloroethane were placed, and the mixture was refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, concentrated, and then the column was separated. The separated solution was concentrated, recrystallized from MeOH, and dried (17 g, 89.5%

4-(7) [화학식 1258]의 합성4- (7) Synthesis of [Formula 1258]

500 mL 둥근바닥플라스크에 10-다이브로모-6-페닐벤조[d]페난스로[3,2-b]사이오펜 17 g(33 mmol), 다이페닐아민 13.3 g(79 mmol), 팔라듐(II)아세테이트 0.29 g(1.3 mmol), 소듐-t-부톡사이드 12.6 g(131 mmol), 톨루엔 200 mL를 넣고 교반하면서 가열하고 60 ℃가 되면 트리-t-부틸포스핀 2.12 g(5.2 mmol)을 넣고 환류시켰다. 반응이 종결되면 상온으로 식히고 반응액을 농축해 컬럼 분리하고 분리액을 농축해 재결정하고, 생성된 결정을 여과하고 건조하였다.(8.6 g, 37.7%)
Dibromo-6-phenylbenzo [d] phenanthro [3,2-b] thiophene (17 g, 33 mmol), diphenylamine (13.3 g, 79 mmol), palladium (II) Butylphosphine (2.12 g, 5.2 mmol) was added to the solution at 60 ° C., and the mixture was refluxed for 2 hours. . After the reaction was completed, the reaction mixture was cooled to room temperature, and the reaction solution was concentrated to separate the column. The separated solution was concentrated and recrystallized, and the resulting crystals were filtered and dried (8.6 g, 37.7%

실시예Example

ITO 글래스의 발광면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 상기 ITO 글래스를 진공 챔버에 장착한 후 베이스 압력이 1×10^-7torr가 되도록 한 후 상기 ITO 위에 CuPc(800Å), α-NPD(300Å) 순으로 성막한 후 본 발명에 따른 화합물(화학식 52, 64, 101, 105, 843, 851, 1258)을 성막(250Å)한 다음 Alq₃(350Å), LiF (5Å), Al (500Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. 호스트물질은 [화학식 1267]화합물로 하였다.
The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the ITO glass was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 ^-7 torr, and then CuPc (800 Å) and α-NPD (300 Å) were sequentially deposited on the ITO. Alq ₃ (350 ANGSTROM), LiF (5 ANGSTROM), and Al (500 ANGSTROM) were sequentially deposited to form an organic electroluminescent device. The host material was a compound of formula (1267).

비교예Comparative Example

상기 실시예와 동일하게 유기전계발광소자를 제조하고, 다만, 발광층의 게스트 화합물로서 하기 [화학식 1266]로 표시되는 피렌계 화합물을 사용하였다.An organic electroluminescent device was prepared in the same manner as in the above Example except that a pyrene compound represented by the following formula (1266) was used as a guest compound in the light emitting layer.

[화학시 1266] [화학식 1267][Chemical formula 1266] [Formula 1267]

본 발명에 따른 유기 발광 화합물을 포함한 유기전계발광소자와 상기 비교예에 따라 제조된 유기전계 발광소자에 대하여 전압, 전류밀도, 휘도, 색 좌표 및 수명을 측정하고 그 결과를 하기 [표 1]에 나타내었다. T97은 휘도가 초기휘도에 비해 97%로 감소되는데 소요되는 시간을 의미한다.Current density, luminance, color coordinates, and lifetime were measured for the organic electroluminescent device including the organic electroluminescent compound according to the present invention and the organic electroluminescent device manufactured according to the comparative example, and the results are shown in Table 1 below Respectively. T97 means the time required for the luminance to be reduced to 97% of the initial luminance.

전압Voltage 전류밀도(㎃/㎠)Current density (mA / cm 2) 휘도(Cd/㎡)Brightness (Cd / m2) CIExCIEx CIEyCIEy T97T97 화학식 52Formula 52 4.094.09 1010 505.4505.4 0.140.14 0.090.09 3535 화학식 64(64) 3.843.84 1010 770.3770.3 0.140.14 0.080.08 3131 화학식 101Formula 101 4.024.02 1010 787.7787.7 0.140.14 0.110.11 7474 화학식 105105 3.783.78 1010 840.3840.3 0.130.13 0.070.07 3333 화학식 843843 3.923.92 1010 513.8513.8 0.130.13 0.120.12 118118 화학식 851851 4.094.09 1010 740740 0.130.13 0.120.12 7070 화학식 12581258 4.164.16 1010 810810 0.130.13 0.130.13 4848 비교예 1Comparative Example 1 5.15.1 1010 560560 0.140.14 0.170.17 2020

상기 [표1]의 결과로부터, 본 발명에 따른 유기 발광 화합물을 포함한 유기전계발광소자는 구동전압이 낮고, 발광효율이 우수한 특성을 보이므로 표시소자, 디스플레이 소자 및 조명 등에 유용하게 사용될 수 있음을 알 수 있다.It can be seen from the results of Table 1 that the organic electroluminescent device including the organic electroluminescent compound according to the present invention has low driving voltage and excellent luminescent efficiency and thus can be used for display devices, Able to know.

10 : 기판 20 : 애노드
30 : 정공주입층 40 : 정공수송층
50 : 유기발광층 60 : 전자수송층
70 : 전자주입층 80 : 캐소드10: substrate 20: anode
30: Hole injection layer 40: Hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

Claims

하기 [화학식 1]로 표시되는 축합아릴 화합물:
[화학식 1]

상기 [화학식 1]에서,
X는 S, O, NR₅, 또는 CR₅R₆이고,
상기 R₅ 내지 R₆은 서로 동일하거나 상이하며, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기 및 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기로 이루어진 군에서 선택되고,
R₁ 내지 R₄는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기 및 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기로 이루어진 군에서 선택되고,
A₁, A₂, B₁ 및 B₂는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기 및 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기로 이루어진 군에서 선택되고,
L₁ 및 L₂는 서로 동일하거나 상이하고, 각각 독립적으로 화학결합 또는 2가의 연결기로서 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬렌기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 50의 헤테로아릴렌기로 이루어진 군에서 선택된다.A condensed aryl compound represented by the following formula 1:
[Chemical Formula 1]

In the above formula (1)
X is S, O, NR _5, or CR ₅ R _6,
R ₅ to R ₆ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroatom such as O, N or S and a heteroaryl group having 3 to 50 carbon atoms,
R ₁ to R ₄ are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, A heteroaryl group having 3 to 50 carbon atoms having an atom, O, N or S,
A ₁ , A ₂ , B ₁ and B ₂ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, An aryl group having 5 to 50 carbon atoms and a heteroaryl group having 3 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S,
L ₁ and L ₂ are the same or different from each other and each independently represents a substituted or unsubstituted C 3 -C 30 cycloalkylene group, a substituted or unsubstituted C 5 -C 50 arylene group and a substituted or unsubstituted arylene group as a divalent linking group Or an unsubstituted heteroarylene group having 3 to 50 carbon atoms.

제 1 항에 있어서,
상기 [화학식 1]은 하기 [화학식 2] 내지 [화학식 17] 및 [화학식 34] 내지 [화학식 49]로 표시되는 군에서 선택되는 어느 하나인 것을 특징으로 하는 축합아릴 화합물:

[화학식 2] [화학식 3]

[화학식 4] [화학식 5]

[화학식 6] [화학식 7]

[화학식 8] [화학식 9]

[화학식 10] [화학식 11]

[화학식 12] [화학식 13]

[화학식 14] [화학식 15]

[화학식 16] [화학식 17]

[화학식 34] [화학식 35]

[화학식 36] [화학식 37]

[화학식 38] [화학식 39]

[화학식 40] [화학식 41]

[화학식 42] [화학식 43]

[화학식 44] [화학식 45]

[화학식 46] [화학식 47]

[화학식 48] [화학식 49]
상기 [화학식 2] 내지 [화학식 17] 및 [화학식 34] 내지 [화학식 49]에서, 상기 R₁ 내지 R₆, A₁, A₂, B₁, B₂, L₁ 및 L₂는 상기 [화학식 1]의 정의와 동일하다.The method according to claim 1,
The condensed aryl compound represented by the above formula (1) is any one selected from the group consisting of the following formulas (2) to (17) and (49)

[Chemical Formula 2] < EMI ID =

[Chemical Formula 4]

[Chemical Formula 6] < EMI ID =

[Chemical Formula 8]

[Chemical Formula 10]

[Chemical Formula 12]

[Chemical Formula 14]

[Chemical Formula 16]

[Chemical Formula 35]

[Chemical Formula 36]

[Chemical Formula 38]

[Chemical Formula 40]

[Chemical Formula 42]

[Chemical Formula 44]

[Chemical Formula 46]

[Chemical Formula 48]
Wherein R ₁ to R ₆ , A ₁ , A ₂ , B ₁ , B ₂ , L ₁ and L ₂ are as defined in the above [Formula 1].

제 1 항에 있어서,
상기 R₁ 내지 R₆, A₁, A₂, B₁, B₂, L₁ 및 L₂에서 "치환 또는 비치환된"은 수소, 중수소 원자, 시아노기, 할로겐기, 탄소수 1 내지 30의 알킬기, 탄소수 5 내지 50의 아릴기 및 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기로 이루어진 군으로부터 1종 이상으로 치환 또는 비치환되는 것을 의미하는 축합아릴 화합물.The method according to claim 1,
The "substituted or unsubstituted" in R ₁ to R ₆ , A ₁ , A ₂ , B ₁ , B ₂ , L ₁ and L ₂ represents a hydrogen atom, a deuterium atom, a cyano group, a halogen group, , An aryl group having 5 to 50 carbon atoms, and a heteroaryl group having 3 to 50 carbon atoms having 0, N, or S as a hetero atom, or a substituted or unsubstituted aryl group.

제 1 항에 있어서,
상기 R₁ 내지 R₆, A₁, A₂, B₁, B₂, L₁, L₂ 및 치환기는 서로 인접한 기와 지방족, 방향족, 지방족헤테로 또는 방향족헤테로의 축합고리를 형성하거나 스피로결합을 형성하는 것을 특징으로 하는 축합아릴 화합물.The method according to claim 1,
Wherein R ₁ to R ₆ , A ₁ , A ₂ , B ₁ , B ₂ , L ₁ , L ₂ and substituents form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with an adjacent group or form a spiro bond &Lt; / RTI >

제 1 항에 있어서,
상기 [화학식 1]은 하기 [화학식 50] 내지 [화학식 1233] 및 [화학식 1250] 내지 [화학식 1265]로 표시되는 화합물 중에서 선택되는 어느 하나인 것을 특징으로 하는 축합아릴 화합물:
[화학식50] [화학식51] [화학식52] [화학식53]

[화학식54] [화학식55] [화학식56] [화학식57]

[화학식58] [화학식59] [화학식60] [화학식61]

[화학식62] [화학식63] [화학식64] [화학식65]

[화학식66] [화학식67] [화학식68] [화학식69]

[화학식70] [화학식71] [화학식72] [화학식73]

[화학식74] [화학식75] [화학식76] [화학식77]

[화학식78] [화학식79] [화학식80] [화학식81]

[화학식82] [화학식83] [화학식84] [화학식85]

[화학식86] [화학식87] [화학식88] [화학식89]

[화학식90] [화학식91] [화학식92] [화학식93]

[화학식94] [화학식95] [화학식96] [화학식97]

[화학식98] [화학식99] [화학식100] [화학식101]

[화학식102] [화학식103] [화학식104] [화학식105]

[화학식106] [화학식107] [화학식108] [화학식109]

[화학식110] [화학식111] [화학식112] [화학식113]

[화학식114] [화학식115] [화학식116] [화학식117]

[화학식118] [화학식119] [화학식120] [화학식121]

[화학식122] [화학식123] [화학식124] [화학식125]

[화학식126] [화학식127] [화학식128] [화학식129]

[화학식130] [화학식131] [화학식132] [화학식133]

[화학식134] [화학식135] [화학식136] [화학식137]

[화학식138] [화학식139] [화학식140] [화학식141]

[화학식142] [화학식143] [화학식144] [화학식145]

[화학식146] [화학식147] [화학식148] [화학식149]

[화학식150] [화학식151] [화학식152] [화학식153]

[화학식154] [화학식155] [화학식156] [화학식157]

[화학식158] [화학식159] [화학식160] [화학식161]

[화학식162] [화학식163] [화학식164] [화학식165]

[화학식166] [화학식167] [화학식168] [화학식169]

[화학식170] [화학식171] [화학식172] [화학식173]

[화학식174] [화학식175] [화학식176] [화학식177]

[화학식178] [화학식179] [화학식180] [화학식181]

[화학식182] [화학식183] [화학식184] [화학식185]

[화학식186] [화학식187] [화학식188] [화학식189]

[화학식190] [화학식191] [화학식192] [화학식193]

[화학식194] [화학식195] [화학식196] [화학식197]

[화학식198] [화학식199] [화학식200] [화학식201]

[화학식202] [화학식203] [화학식204] [화학식205]

[화학식206] [화학식207] [화학식208] [화학식209]

[화학식210] [화학식211] [화학식212] [화학식213]

[화학식214] [화학식215] [화학식216] [화학식217]

[화학식218] [화학식219] [화학식220] [화학식221]

[화학식222] [화학식223] [화학식224] [화학식225]

[화학식226] [화학식227] [화학식228] [화학식229]

[화학식230] [화학식231] [화학식232] [화학식233]

[화학식234] [화학식235] [화학식236] [화학식237]

[화학식238] [화학식239] [화학식240] [화학식241]

[화학식242] [화학식243] [화학식244] [화학식245]

[화학식246] [화학식247] [화학식248] [화학식249]

[화학식250] [화학식251] [화학식252] [화학식253]

[화학식254] [화학식255] [화학식256] [화학식257]

[화학식258] [화학식259] [화학식260] [화학식261]

[화학식262] [화학식263] [화학식264] [화학식265]

[화학식266] [화학식267] [화학식268] [화학식269]

[화학식270] [화학식271] [화학식272] [화학식273]

[화학식274] [화학식275] [화학식276] [화학식277]

[화학식278] [화학식279] [화학식280] [화학식281]

[화학식282] [화학식283] [화학식284] [화학식285]

[화학식286] [화학식287] [화학식288] [화학식289]

[화학식290] [화학식291] [화학식292] [화학식293]

[화학식294] [화학식295] [화학식296] [화학식297]

[화학식298] [화학식299] [화학식300] [화학식301]

[화학식302] [화학식303] [화학식304] [화학식305]

[화학식306] [화학식307] [화학식308] [화학식309]

[화학식310] [화학식311] [화학식312] [화학식313]

[화학식314] [화학식315] [화학식316] [화학식317]

[화학식318] [화학식319] [화학식320] [화학식321]

[화학식322] [화학식323] [화학식324] [화학식325]

[화학식326] [화학식327] [화학식328] [화학식329]

[화학식330] [화학식331] [화학식332] [화학식333]

[화학식334] [화학식335] [화학식336] [화학식337]

[화학식338] [화학식339] [화학식340] [화학식341]

[화학식342] [화학식343] [화학식344] [화학식345]

[화학식346] [화학식347] [화학식348] [화학식349]

[화학식350] [화학식351] [화학식352] [화학식353]

[화학식354] [화학식355] [화학식356] [화학식357]

[화학식358] [화학식359] [화학식360] [화학식361]

[화학식362] [화학식363] [화학식364] [화학식365]

[화학식366] [화학식367] [화학식368] [화학식369]

[화학식370] [화학식371] [화학식372] [화학식373]

[화학식374] [화학식375] [화학식376] [화학식377]

[화학식378] [화학식379] [화학식380] [화학식381]

[화학식382] [화학식383] [화학식384] [화학식385]

[화학식386] [화학식387] [화학식388] [화학식389]

[화학식390] [화학식391 ] [화학식392] [화학식393]

[화학식394] [화학식395] [화학식396] [화학식397]

[화학식398] [화학식399] [화학식400] [화학식401]

[화학식402] [화학식403] [화학식404] [화학식405]

[화학식406] [화학식407] [화학식408] [화학식409]

[화학식410] [화학식411] [화학식412] [화학식413]

[화학식414] [화학식415] [화학식416] [화학식417]

[화학식418] [화학식419] [화학식420] [화학식421]

[화학식422] [화학식423] [화학식424] [화학식425]

[화학식426] [화학식427] [화학식428] [화학식429]

[화학식430] [화학식431] [화학식432] [화학식433]

[화학식434] [화학식435] [화학식436] [화학식437]

[화학식438] [화학식439] [화학식440] [화학식441]

[화학식442] [화학식443] [화학식444] [화학식445]

[화학식446] [화학식447] [화학식448] [화학식449]

[화학식450] [화학식451] [화학식452] [화학식453]

[화학식454] [화학식455] [화학식456] [화학식457]

[화학식458] [화학식459] [화학식460] [화학식461]

[화학식462] [화학식463] [화학식464] [화학식465]

[화학식466] [화학식467] [화학식468] [화학식469]

[화학식470] [화학식471] [화학식472] [화학식473]

[화학식474] [화학식475] [화학식476] [화학식477]

[화학식478] [화학식479] [화학식480] [화학식481]

[화학식482] [화학식483] [화학식484] [화학식485]

[화학식486] [화학식487] [화학식488] [화학식489]

[화학식490] [화학식491] [화학식492] [화학식493]

[화학식494] [화학식495] [화학식496] [화학식497]

[화학식498] [화학식499] [화학식500] [화학식501]

[화학식502] [화학식503] [화학식504] [화학식505]

[화학식506] [화학식507] [화학식508] [화학식509]

[화학식510] [화학식511] [화학식512] [화학식513]

[화학식514] [화학식515] [화학식516] [화학식517]

[화학식518] [화학식519] [화학식520] [화학식521]

[화학식522] [화학식523] [화학식524] [화학식525]

[화학식526] [화학식527] [화학식528] [화학식529]

[화학식530] [화학식531] [화학식532] [화학식533]

[화학식534] [화학식535] [화학식536] [화학식537]

[화학식538] [화학식539] [화학식540] [화학식541]

[화학식542] [화학식543] [화학식544] [화학식545]

[화학식546] [화학식547] [화학식548] [화학식549]

[화학식550] [화학식551] [화학식552] [화학식553]

[화학식554] [화학식555] [화학식556] [화학식557]

[화학식558] [화학식559] [화학식560] [화학식561]

[화학식562] [화학식563] [화학식564] [화학식565]

[화학식566] [화학식567] [화학식568] [화학식569]

[화학식570] [화학식571] [화학식572] [화학식573]

[화학식574] [화학식575] [화학식576] [화학식577]

[화학식578] [화학식579] [화학식580] [화학식581]

[화학식582] [화학식583] [화학식584] [화학식585]

[화학식586] [화학식587] [화학식588] [화학식589]

[화학식590] [화학식591] [화학식592] [화학식593]

[화학식594] [화학식595] [화학식596] [화학식597]

[화학식598] [화학식599] [화학식600] [화학식601]

[화학식602] [화학식603] [화학식604] [화학식605]

[화학식606] [화학식607] [화학식608] [화학식609]

[화학식610] [화학식611] [화학식612] [화학식613]

[화학식614] [화학식615] [화학식616] [화학식617]

[화학식618] [화학식619] [화학식620] [화학식621]

[화학식622] [화학식623] [화학식624] [화학식625]

[화학식626] [화학식627] [화학식628] [화학식629]

[화학식630] [화학식631] [화학식632] [화학식633]

[화학식634] [화학식635] [화학식636] [화학식637]

[화학식638] [화학식639] [화학식640] [화학식641]

[화학식642] [화학식643] [화학식644] [화학식645]

[화학식646] [화학식647] [화학식648] [화학식649]

[화학식650] [화학식651] [화학식652] [화학식653]

[화학식654] [화학식655] [화학식656] [화학식657]

[화학식658] [화학식659] [화학식660] [화학식661]

[화학식662] [화학식663] [화학식664] [화학식665]

[화학식666] [화학식667] [화학식668] [화학식669]

[화학식670] [화학식671] [화학식672] [화학식673]

[화학식674] [화학식675] [화학식676] [화학식677]

[화학식678] [화학식679] [화학식680] [화학식681]

[화학식682] [화학식683] [화학식684] [화학식685]

[화학식686] [화학식687] [화학식688] [화학식689]

[화학식690] [화학식691] [화학식692] [화학식693]

[화학식694] [화학식695] [화학식696] [화학식697]

[화학식698] [화학식699] [화학식700] [화학식701]

[화학식702] [화학식703] [화학식704] [화학식705]

[화학식706] [화학식707] [화학식708] [화학식709]

[화학식710] [화학식711] [화학식712] [화학식713]

[화학식714] [화학식715] [화학식716] [화학식717]

[화학식718] [화학식719] [화학식720] [화학식721]

[화학식722] [화학식723] [화학식724] [화학식725]

[화학식726] [화학식727] [화학식728] [화학식729]

[화학식730] [화학식731] [화학식732] [화학식733]

[화학식734] [화학식735] [화학식736] [화학식737]

[화학식738] [화학식739] [화학식740] [화학식741]

[화학식742] [화학식743] [화학식744] [화학식745]

[화학식746] [화학식747] [화학식748] [화학식749]

[화학식750] [화학식751] [화학식752] [화학식753]

[화학식754] [화학식755] [화학식756] [화학식757]

[화학식758] [화학식759] [화학식760] [화학식761]

[화학식762] [화학식763] [화학식764] [화학식765]

[화학식766] [화학식767] [화학식768] [화학식769]

[화학식770] [화학식771] [화학식772] [화학식773]

[화학식774] [화학식775] [화학식776] [화학식777]

[화학식778] [화학식779] [화학식780] [화학식781]

[화학식782] [화학식783] [화학식784] [화학식785]

[화학식786] [화학식787] [화학식788] [화학식789]

[화학식790] [화학식791] [화학식792] [화학식793]

[화학식794] [화학식795] [화학식796] [화학식797]

[화학식798] [화학식799] [화학식800] [화학식801]

[화학식802] [화학식803] [화학식804] [화학식805]

[화학식806] [화학식807] [화학식808] [화학식809]

[화학식810] [화학식811] [화학식812] [화학식813]

[화학식814] [화학식815] [화학식816] [화학식817]

[화학식818] [화학식819] [화학식820] [화학식821]

[화학식822] [화학식823] [화학식824] [화학식825]

[화학식826] [화학식827] [화학식828] [화학식829]

[화학식830] [화학식831] [화학식832] [화학식833]

[화학식834] [화학식835] [화학식836] [화학식837]

[화학식838] [화학식839] [화학식840] [화학식841]

[화학식842] [화학식843] [화학식844] [화학식845]

[화학식846] [화학식847] [화학식848] [화학식849]

[화학식850] [화학식851] [화학식852] [화학식853]

[화학식854] [화학식855] [화학식856] [화학식857]

[화학식858] [화학식859] [화학식860] [화학식861]

[화학식862] [화학식863] [화학식864] [화학식865]

[화학식866] [화학식867] [화학식868] [화학식869]

[화학식870] [화학식871] [화학식872] [화학식873]

[화학식874] [화학식875] [화학식876] [화학식877]

[화학식878] [화학식879] [화학식880] [화학식881]

[화학식882] [화학식883] [화학식884] [화학식885]

[화학식886] [화학식887] [화학식888] [화학식889]

[화학식890] [화학식891] [화학식892] [화학식893]

[화학식894] [화학식895] [화학식896] [화학식897]

[화학식898] [화학식899] [화학식900] [화학식901]

[화학식902] [화학식903] [화학식904] [화학식905]

[화학식906] [화학식907] [화학식908] [화학식909]

[화학식910] [화학식911] [화학식912] [화학식913]

[화학식914] [화학식915] [화학식916] [화학식917]

[화학식918] [화학식919] [화학식920] [화학식921]

[화학식922] [화학식923] [화학식924] [화학식925]

[화학식926] [화학식927] [화학식928] [화학식929]

[화학식930] [화학식931] [화학식932] [화학식933]

[화학식934] [화학식935] [화학식936] [화학식937]

[화학식938] [화학식939] [화학식940] [화학식941]

[화학식942] [화학식943] [화학식944] [화학식945]

[화학식946] [화학식947] [화학식948] [화학식949]

[화학식950] [화학식951] [화학식952] [화학식953]

[화학식954] [화학식955] [화학식956] [화학식957]

[화학식958] [화학식959] [화학식960] [화학식961]

[화학식962] [화학식963] [화학식964] [화학식965]

[화학식966] [화학식967] [화학식968] [화학식969]

[화학식970] [화학식971] [화학식972] [화학식973]

[화학식974] [화학식975] [화학식976] [화학식977]

[화학식978] [화학식979] [화학식980] [화학식981]

[화학식982] [화학식983] [화학식984] [화학식985]

[화학식986] [화학식987] [화학식988] [화학식989]

[화학식990] [화학식991] [화학식992] [화학식993]

[화학식994] [화학식995] [화학식996] [화학식997]

[화학식998] [화학식999] [화학식1000] [화학식1001]

[화학식1002] [화학식1003] [화학식1004] [화학식1005]

[화학식1006] [화학식1007] [화학식1008] [화학식1009]

[화학식1010] [화학식1011] [화학식1012] [화학식1013]

[화학식1014] [화학식1015] [화학식1016] [화학식1017]

[화학식1018] [화학식1019] [화학식1020] [화학식1021]

[화학식1022] [화학식1023] [화학식1024] [화학식1025]

[화학식1026] [화학식1027] [화학식1028] [화학식1029]

[화학식1030] [화학식1031] [화학식1032] [화학식1033]

[화학식1034] [화학식1035] [화학식1036] [화학식1037]

[화학식1038] [화학식1039] [화학식1040] [화학식1041]

[화학식1042] [화학식1043] [화학식1044] [화학식1045]

[화학식1046] [화학식1047] [화학식1048] [화학식1049]

[화학식1050] [화학식1051] [화학식1052] [화학식1053]

[화학식1054] [화학식1055] [화학식1056] [화학식1057]

[화학식1058] [화학식1059] [화학식1060] [화학식1061]

[화학식1062] [화학식1063] [화학식1064] [화학식1065]

[화학식1066] [화학식1067] [화학식1068] [화학식1069]

[화학식1070] [화학식1071] [화학식1072] [화학식1073]

[화학식1074] [화학식1075] [화학식1076] [화학식1077]

[화학식1078] [화학식1079] [화학식1080] [화학식1081]

[화학식1082] [화학식1083] [화학식1084] [화학식1085]

[화학식1086] [화학식1087] [화학식1088] [화학식1089]

[화학식1090] [화학식1091] [화학식1092] [화학식1093]

[화학식1094] [화학식1095] [화학식1096] [화학식1097]

[화학식1098] [화학식1099] [화학식1100] [화학식1101]

[화학식1102] [화학식1103] [화학식1104] [화학식1105]

[화학식1106] [화학식1107] [화학식1108] [화학식1109]

[화학식1110] [화학식1111] [화학식1112] [화학식1113]

[화학식1114] [화학식1115] [화학식1116] [화학식1117]

[화학식1118] [화학식1119] [화학식1120] [화학식1121]

[화학식1122] [화학식1123] [화학식1124] [화학식1125]

[화학식1126] [화학식1127] [화학식1128] [화학식1129]

[화학식1130] [화학식1131] [화학식1132] [화학식1133]

[화학식1134] [화학식1135] [화학식1136] [화학식1137]

[화학식1138] [화학식1139] [화학식1140] [화학식1141]

[화학식1142] [화학식1143] [화학식1144] [화학식1145]

[화학식1146] [화학식1147] [화학식1148] [화학식1149]

[화학식1150] [화학식1151] [화학식1152] [화학식1153]

[화학식1154] [화학식1155] [화학식1156] [화학식1157]

[화학식1158] [화학식1159] [화학식1160] [화학식1161]

[화학식1162] [화학식1163] [화학식1164] [화학식1165]

[화학식1166] [화학식1167] [화학식1168] [화학식1169]

[화학식1170] [화학식1171] [화학식1172] [화학식1173]

[화학식1174] [화학식1175] [화학식1176] [화학식1177]

[화학식1178] [화학식1179] [화학식1180] [화학식1181]

[화학식1182] [화학식1183] [화학식1184] [화학식1185]

[화학식1186] [화학식1187] [화학식1188] [화학식1189]

[화학식1190] [화학식1191] [화학식1192] [화학식1193]

[화학식1194] [화학식1195] [화학식1196] [화학식1197]

[화학식1198] [화학식1199] [화학식1200] [화학식1201]

[화학식1202] [화학식1203] [화학식1204] [화학식1205]

[화학식1206] [화학식1207] [화학식1208] [화학식1209]

[화학식1210] [화학식1211] [화학식1212] [화학식1213]

[화학식1214] [화학식1215] [화학식1216] [화학식1217]

[화학식1218] [화학식1219] [화학식1220] [화학식1221]

[화학식1222] [화학식1223] [화학식1224] [화학식1225]

[화학식1226] [화학식1227] [화학식1228] [화학식1229]

[화학식1230] [화학식1231] [화학식1232] [화학식1233]

[화학식1250] [화학식1251] [화학식1252] [화학식1253]

[화학식1254] [화학식1255] [화학식1256] [화학식1257]

[화학식1258] [화학식1259] [화학식1260] [화학식1261]

[화학식1262] [화학식1263] [화학식1264] [화학식1265]

The method according to claim 1,
The condensed aryl compound represented by Formula 1 is any one selected from compounds represented by the following Chemical Formulas 50 to 1233 and Chemical Formula 1250 to Chemical Formula 1265:
[Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61]

[Chemical Formula 62] [Chemical Formula 65] [Chemical Formula 65]

[Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69]

[Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73]

[Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77]

[Formula 79] [Formula 80] [Formula 81]

[Chemical Formula 82]

[Chemical Formula 88] [Chemical Formula 88] [Chemical Formula 89]

[Chemical Formula 91] [Chemical Formula 92] [Chemical Formula 93]

[Chemical Formula 95] [Chemical Formula 96] [Chemical Formula 97]

[Chemical Formula 100] [Chemical Formula 100]

[Formula 103] [Formula 103]

[Formula 110] [Formula 111] [Formula 112] [Formula 113]

[Chemical Formula 115]

[Chemical Formula 120] [Chemical Formula 120] [Chemical Formula 120]

[Formula 124] [Formula 124] [Formula 125]

[Formula 126] < EMI ID = 129.1 >

[Formula 130] < EMI ID = 131.0 >

[Formula 135] [Formula 135] [Formula 137]

[Chemical Formula 140] [Chemical Formula 140] [Chemical Formula 140]

[Chemical Formula 144] [Chemical Formula 144] [Chemical Formula 145]

[Chemical Formula 146] [Chemical Formula 148] [Chemical Formula 149]

[Formula 15] [Formula 15] [Formula 15] [Formula 15]

[Chemical Formula 155] [Chemical Formula 156] [Chemical Formula 157]

[Formula 15] [Formula 15] [Formula 15] [Formula 15] [Formula 15]

[166] [165] [165]

[Formula 166] [Formula 169] [Formula 169]

[173] [173] [173]

[Formula 177] [Formula 177] [Formula 177]

[Formula 181] [Formula 181] [Formula 181] [Formula 181]

[Formula 182] [Formula 184] [Formula 184]

[Formula 188] [Formula 188] [Formula 189]

[Formula 19] [Formula 19] [Formula 193] [Formula 193]

[Formula 19] [Formula 19] [Formula 19] [Formula 19] [Formula 19]

[201] [201] [201]

[Chemical Formula 203]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 210] [Chemical Formula 212] [Chemical Formula 213]

[Formula 21] [Formula 21] [Formula 21] [Formula 21]

[Formula 21] < EMI ID =

[Formula 22] < EMI ID =

[229] [229] [229]

[233] [232] [233]

[237] [237] [237]

[238] [240] [248]

[245] [242] [242]

[248] [248] [249]

[Formula 252] [Formula 253]

[Formula 25] [Formula 25] [Formula 25] [Formula 25]

[Formula 252] [Chemical Formula 260] [Chemical Formula 261]

[Formula 262] [Formula 264] [Formula 265]

[268] [268] [268] [269]

[273] [272] [272] [272]

(277) [Formula 277] [Formula 277]

(281) [Chemical Formula 280] [Chemical Formula 280]

[Formula 28] [Formula 28] [Formula 28]

[Formula 288] [Formula 288] [Formula 289]

[290] [290] [292] [293]

(297) [Chemical Formula 297] [Chemical Formula 297]

[Chemical Formula 300] [Chemical Formula 301]

[Chemical Formula 303] [Chemical Formula 304]

[Formula 309] [Formula 309]

[311] [311] [313] [313]

[314] [315] [316]

[311] [318] [320]

(325), wherein R < 1 >

[328] [328] [329]

[333] [333] [333]

(337) [Chemical Formula 337] [Chemical Formula 337]

[331] [333] [340] [341]

(345) [Formula 344] [Formula 345]

[Chemical Formula 347] [Chemical Formula 349] [Chemical Formula 349]

[353] [353] [353]

(357) [Chemical Formula 357] [Chemical Formula 357]

[Formula 35] [Formula 35] [Formula 35]

(365) [Chemical Formula 365] [Chemical Formula 365]

[368] [369] [369] [369]

[370] [370]

[Formula 377] [Formula 377] [Formula 377]

[380] [380] [380] [380]

[Formula 38] [Formula 384] [Formula 385]

[Formula 388] [Formula 388] [Formula 389]

[390] [390] [393] [393]

[397] [396] [396]

[Formula 39] [Formula 39] [Formula 39]

[402] [40] [40] [40] [40]

[Chemical Formula 409] [Chemical Formula 409]

[410] [410] [411] [411]

(417) [Chemical Formula 417] [Chemical Formula 417]

[Formula 41] [Formula 41]

[422] [422] [422] [422]

[428] [428] [428] [429]

[Chemical Formula 433] [Chemical Formula 433] [Chemical Formula 433]

[Chemical Formula 437] [Chemical Formula 437] [Chemical Formula 437]

[Formula 43] [Formula 43] [Formula 43]

[Chemical Formula 445] [Chemical Formula 445] [Chemical Formula 445]

[Chemical Formula 447] [Chemical Formula 449] [Chemical Formula 449]

[Formula 45] [Formula 453] [Formula 453]

[Chemical Formula 457] [Chemical Formula 457] [Chemical Formula 457]

[Formula 456] [Formula 460] [Formula 461]

[Chemical Formula 463] [Chemical Formula 465] [Chemical Formula 465]

[Formula 466] [Formula 466] [Formula 469]

[Formula 472] [Formula 472] [Formula 473]

[Chemical Formula 477] [Chemical Formula 477] [Chemical Formula 477]

[488] [488] [488] [488]

[Formula 48] [Formula 48] [Formula 48]

[488] [488] [488] [488] [488]

[Formula 49] [Formula 493] [Formula 493]

[Chemical Formula 497] [Chemical Formula 497] [Chemical Formula 497]

[Formula 49] [Chemical Formula 500] [Chemical Formula 501]

[Chemical Formula 503] [Chemical Formula 505]

[Formula 508] [Formula 509]

[510] [511] [512]

[514] [515] [515] [517]

[518] [521] [521]

[522] [522] [522] [522]

[529] [528] [529]

[533] [533] [533] [533]

[Chemical Formula 537] [Chemical Formula 537] [Chemical Formula 537]

[538] [539] [539]

[545] [544] [544] [545]

[549] [548] [548] [549]

[551] [552] [552]

[557] [557] [557] [557]

[569] [569] [569]

565] [Chemical Formula 565] [Chemical Formula 565]

[569] [569] [569] [569]

[573] [572] [572] [572]

(577) [Chemical Formula 577] [Chemical Formula 577] [Chemical Formula 577]

[578] [589] [589]

[582] [582] [582]

[588] [588] [588] [589]

[Formula 599] [Formula 593] [Formula 593]

[Chemical Formula 597] [Chemical Formula 597] [Chemical Formula 597]

[Chemical Formula 601] [Chemical Formula 601]

[602] [603] [603]

[608] [609] [609]

[Formula 611] [Formula 611]

[617] [616] [616]

[618] [618] [618]

[622] [622] [622] [622]

[629] [629] [629]

[Formula 633] [Formula 632] [Formula 633]

[Formula 636] [Formula 636] [Formula 637]

[638] [638] [638]

(645) [0604] The compound of the formula (645)

[Formula 648] [Formula 648]

[653] [653] [653]

[657] [657] [657] [657]

[Formula 65] [Formula 65] [Formula 65]

[663] [662] [662]

[669] [669] [669]

[Formula 673] [Formula 673] [Formula 673]

(677) [Chemical Formula 677] [Chemical Formula 677] [Chemical Formula 677]

[678] [678] [678]

[688] [688] [688] [688]

[692] [692] [692]

[697] [697] [697] [697]

[708] [709] [709]

[703] [703] [705]

[707] [709] [709] [709]

[712] [712] [712] [712]

[717] [717] [717]

[721] [720] [720]

[732] [722] [722] [722]

[729] [729] [729] [729]

[733] [733] [733]

[737] [737] [737]

[738] [739] [749]

[Chemical Formula 744] [Chemical Formula 744] [Chemical Formula 745]

[748] [748] [749] [749]

[Formula 753] [Formula 753]

[757] [757] [757] [757]

[Formula 756] [Formula 756] [Formula 751]

[763] [763] [764] [765]

[Formula 766] [Chemical Formula 769] [Chemical Formula 769]

[773] [772] [772]

[777] [777] [777] [777]

[Formula 778] [Formula 780]

[788] [788] [788] [788]

[793] [792] [792]

[797] [797] [797] [797]

[Formula 798] [Formula 800] [Formula 801]

[Formula 804] [Formula 804]

[808] [808] [808]

[812] [812] [812] [811]

[Formula 814] [Formula 816] [Formula 816]

[821] [820] [820]

[822] [822] [824]

[828] [828] [828] [829]

(832) [Formula 832] [Formula 832]

[837] [837] [837]

[Formula 838] [Formula 840] [Formula 841]

[842] [844] [844]

[848] [848] [848] [848]

[Formula 853] < EMI ID =

[Formula 857] [Formula 857] [Formula 857]

[868] [869] < EMI ID =

[862] [863] [864]

[868] [868] [869]

[873] [872] [873] [873]

[877] [877] [877] [877]

[878] [878] [888] [888]

[Formula 88] [Formula 88] [Formula 884]

[Formula 888] [Formula 888] [Formula 889]

[892] [892] [892]

[897] [897] [897]

[898] [909] [909]

[Formula 903] [Formula 904]

[Formula 908] [Formula 909] [Formula 909]

[Formula 911] [Formula 912] [Formula 913]

[Formula 914] [Formula 914]

[921] [920]

(925) [Formula 922] < EMI ID =

[929] [929] [929] [929]

[931] [931] [931]

[936] [936] [936]

[Chemical Formula 940] [Chemical Formula 940]

[Chemical Formula 944] [Chemical Formula 944] [Chemical Formula 945]

[Chemical Formula 947] [Chemical Formula 948] [Chemical Formula 949]

[953] [952] [953]

[Chemical Formula 957] [Chemical Formula 957] [Chemical Formula 957]

[Chemical Formula 959]

[Chemical Formula 965]

[Chemical Formula 969] [Chemical Formula 969] [Chemical Formula 969]

[973] [972] [973] [973]

[977] [977] [977] [977]

[Formula 978] [Formula 978]

[982] [982] [982] [982]

[988] [988] [988] [988]

[Formula 99] [Formula 993] [Formula 993]

[Formula 997] [Formula 997] [Formula 997]

[Formula 991] [Chemical Formula 1000] [Chemical Formula 1001]

[Formula 1003] [Formula 1004] [Formula 1005]

(1009) [Chemical Formula 1009] [Chemical Formula 1009]

[1010] [Chemical Formula 1011] [Chemical Formula 1013]

Wherein R < 1 > and R < 2 &

Embedded image In the formula,

[1022] [1022] [1022]

[1028] [1028] [1029]

[0103] The compound of the formula [1030]

[1036] [1036] [1036]

[1038] [1038]

[1045] [1045] [1045]

[1049] [1048] [1049]

[1053] [1053] [1053]

[1057] [1055] [1055]

[1069] [1069] [1069]

[1066] [1066] [1066] [1066]

[1066] [1069] [1066]

(1073) [Formula 1073] < EMI ID =

[1077] [Formula 1077] [Formula 1077]

[1088] [1089] [1089]

[1088] [1088] [1088] [1088]

[1093] [1092] [1093]

[1097] [1099] [1099]

[Formula 1110] [Formula 1110] [Formula 1101]

[Formula 110] [Formula 1104]

[Formula 1111] [Formula 1111] [Formula 1111] [Formula 1113]

[Formula 1111] [Formula 1111]

[Formula 1121] [Formula 1120]

[Formula 1125] [Formula 1122]

[Formula 1128] [Formula 1128] [Formula 1129]

[Formula 1133] [Formula 1132] [Formula 1133]

[Formula 1137] [Formula 1137]

[Formula 1111] [Formula 1111]

[Formula 1144] [Formula 1144] [Formula 1145]

[Formula 114] [Formula 1144]

[1153] [1153] [1153]

[1157] [1157] [1157]

[Formula 1151] [Formula 1151]

[Formula 1165] [Formula 1165]

[1169] [1169]

[1173] [1172] [1173]

[Chemical Formula 1177] [Chemical Formula 1177]

(1181) [Formula 1181]

[1182] [1183] [1184]

[Formula 1188] [Formula 1188] [Formula 1189]

[Formula 1191] [Formula 1192] [Formula 1193] [Formula 1193]

[Formula 1195] [Formula 1195] [Formula 1197]

[Formula 11] [Formula 11]

[Formula 120] [Formula 1203]

(1209) [Formula 1206]

[Formula 1212] [Formula 1212] [Formula 1212]

[Formula 1214] [Formula 1214]

[Formula 1221] [Formula 1220] [Formula 1221]

[Formula 1222] [Formula 1222] [Formula 1225]

[1229] [1229] [1227]

[Formula 1232] [Formula 1232]

[1253] [1251] [1253] [1253]

[1256] [1256] [1257]

[1256] [1256] [1256]

[Formula 1236] [Formula 1236] [Formula 1265]

애노드;
캐소드; 및
상기 애노드와 상기 캐소드 사이에 개재되며, 제 1 항 내지 제 5 항 중 어느 한 항의 축합아릴 화합물을 포함하는 유기전계발광소자.Anode;
Cathode; And
An organic electroluminescent element interposed between the anode and the cathode and comprising the condensed aryl compound according to any one of claims 1 to 5.

제 6 항에 있어서,
상기 축합아릴 화합물은 상기 애노드와 상기 캐소드 사이의 발광층 중에 포함되는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
Wherein the condensed aryl compound is contained in the light emitting layer between the anode and the cathode.

제 7 항에 있어서,
상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함하는 것을 특징으로 하는 유기전계발광소자.8. The method of claim 7,
Wherein at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron blocking layer, a hole blocking layer, an electron transporting layer and an electron injecting layer is further interposed between the anode and the cathode.

제 8 항에 있어서,
상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성되는 것을 특징으로 하는 유기전계발광소자.9. The method of claim 8,
Wherein at least one layer selected from the group consisting of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecular deposition method or a solution process.

제 6 항에 있어서,
상기 유기전계발광소자는 표시소자, 디스플레이 소자, 또는 단색 또는 백색 조명용 소자에 사용되는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
Wherein the organic electroluminescent device is used in a display device, a display device, or a device for monochromatic or white illumination.