KR20130101449A - New dibenzotetracene-based organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

New dibenzotetracene-based organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDF

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KR20130101449A
KR20130101449A KR1020130003524A KR20130003524A KR20130101449A KR 20130101449 A KR20130101449 A KR 20130101449A KR 1020130003524 A KR1020130003524 A KR 1020130003524A KR 20130003524 A KR20130003524 A KR 20130003524A KR 20130101449 A KR20130101449 A KR 20130101449A
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김복영
안중복
현승학
이재성
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(주)씨에스엘쏠라
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine

Abstract

PURPOSE: A dibenzotetracene-based derivative is provided to have excellent luminous efficiency, color purity, and lifetime, and to have excellent structure with moderate color coordination. CONSTITUTION: A dibenzotetracene-based derivative is represented by chemical formula F. In an organic electroluminescent device, one or more organic thin film layers including a light emitting layer are inserted between a negative electrode and a positive electrode. At least one layer of the organic thin film layers includes one or a combination of two or more kinds of the dibenzotetracene-based derivative. The dibenzotetracene-based derivative contains a fluorescence green host compound or a light-emitting green dopant compound in the light emitting layer of the organic thin film layers.

Description

신규한 디벤조테트라센계 유기 발광 화합물 및 이를 포함하는 유기 전기발광 소자{New dibenzotetracene-based organic electroluminescent compounds and organic electroluminescent device comprising the same}New dibenzotetracene-based organic luminescent compound and organic electroluminescent device comprising the same {New dibenzotetracene-based organic electroluminescent compounds and organic electroluminescent device comprising the same}

본 발명은 유기 발광 화합물 및 이를 포함하는 유기 전기발광 소자에 관한 것으로, 보다 구체적으로는 신규한 디벤조테트라센계 유기 발광 화합물 및 이를 도판트로서 채용하고 있는 유기 발광 소자에 관한 것이다.        The present invention relates to an organic light emitting compound and an organic electroluminescent device comprising the same, and more particularly to a novel dibenzotetracene-based organic light emitting compound and an organic light emitting device employing the same as a dopant.

표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사에서는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Co., Ltd. developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].

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

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

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

본 발명은, 종래기술의 문제를 해결하기 위하여 안출된 것으로서, 발광 효율이 좋고, 재료의 색순도 및 수명특성이 뛰어나며, 적절한 색좌표를 나타내는 우수한 골격을 갖는 유기 발광 화합물인 디벤조테트라센 계 유도체 및 이를 발광재료로 채용한 고효율 및 장수명 특성을 갖는 유기 전기발광 소자를 제공하는 것을 목적으로 한다.The present invention has been made to solve the problems of the prior art, a dibenzotetracene-based derivative which is an organic light emitting compound having good luminous efficiency, excellent color purity and lifespan characteristics of materials, and an excellent skeleton showing appropriate color coordinates, and the same. An object of the present invention is to provide an organic electroluminescent device having high efficiency and long life characteristics employed as a light emitting material.

본 발명은,According to the present invention,

하기 화학식F로 표시되는 디벤조테트라센계 유도체(indenoindene-based derivatives)를 제공한다:It provides dibenzotetracene-based derivatives represented by the formula (F):

[화학식F]Formula F]

Figure pat00001

Figure pat00001

상기 식에서,Where

R1 내지 R3는 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기 이거나;R 1 to R 3 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , or a Si (C 6 H 5 ) 3 group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기이거나;C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , Triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups

Figure pat00002
,
Figure pat00003
,
Figure pat00004
,
Figure pat00005
,
Figure pat00006
,
Figure pat00007
,
Figure pat00008
,
Figure pat00009
및
Figure pat00010
이거나; 또는
Figure pat00002
,
Figure pat00003
,
Figure pat00004
,
Figure pat00005
,
Figure pat00006
,
Figure pat00007
,
Figure pat00008
,
Figure pat00009
And
Figure pat00010
; or

Figure pat00011
이며;
Figure pat00011
;

A 및 B는 각각 독립적으로 C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기 이거나;A and B are each independently C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Or a Si (C 6 H 5 ) 3 group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기 이거나;C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , Triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups

Figure pat00012
,
Figure pat00013
,
Figure pat00014
,
Figure pat00015
,
Figure pat00016
,
Figure pat00017
,
Figure pat00018
,
Figure pat00019
및
Figure pat00020
이거나;
Figure pat00012
,
Figure pat00013
,
Figure pat00014
,
Figure pat00015
,
Figure pat00016
,
Figure pat00017
,
Figure pat00018
,
Figure pat00019
And
Figure pat00020
;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 및 디히드로인돌기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이거나;C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , 30-30 aryl substituted with one or more substituents selected from the group consisting of triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, and dihydroindole group Or a heteroaryl group of 5 to 60;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups

Figure pat00021
,
Figure pat00022
,
Figure pat00023
,
Figure pat00024
,
Figure pat00025
,
Figure pat00026
,
Figure pat00027
,
Figure pat00028
및
Figure pat00029
로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이거나;
Figure pat00021
,
Figure pat00022
,
Figure pat00023
,
Figure pat00024
,
Figure pat00025
,
Figure pat00026
,
Figure pat00027
,
Figure pat00028
And
Figure pat00029
6 to 30 aryl groups or 5 to 60 heteroaryl groups substituted with one or more substituents selected from the group consisting of;

Figure pat00030
이며;
Figure pat00030
;

상기 Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로, Ar1, Ar2, Ar3 and Ar4 are each independently,

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기 이거나;C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , Triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups

Figure pat00031
,
Figure pat00032
,
Figure pat00033
,
Figure pat00034
,
Figure pat00035
,
Figure pat00036
,
Figure pat00037
,
Figure pat00038
및
Figure pat00039
이며;
Figure pat00031
,
Figure pat00032
,
Figure pat00033
,
Figure pat00034
,
Figure pat00035
,
Figure pat00036
,
Figure pat00037
,
Figure pat00038
And
Figure pat00039
;

상기 Ar1 및 Ar2, 및 Ar3 및 Ar4는 각각 독립적으로 서로 결합하여 하나 이상의 C1~C5의 알킬기로 치환 또는 비치환된 5원환 내지 8원환의 고리를 형성할 수 있으며;Ar 1 and Ar 2, and Ar 3 and Ar 4 may be each independently bonded to each other to form a 5- to 8-membered ring unsubstituted or substituted with one or more C 1 to C 5 alkyl groups;

상기 R4, R5, R6, R7, R8 및 R9은 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기이며;R4, R5, R6, R7, R8 and R9 are each independently a hydrogen atom, C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, Nitrile, CF 3 , Si (CH 3 ) 3 , or Si (C 6 H 5 ) 3 groups;

상기 X1, X2, X3, X4는 각각 독립적으로 탄소원자, 질소원자 또는 황원자이며; X 1, X 2, X 3 and X 4 are each independently a carbon atom, a nitrogen atom or a sulfur atom;

상기 Y1, Y2, Y3, Y4는 각각 독립적으로 탄소원자, 질소원자 또는 황원자이다.
Y1, Y2, Y3, and Y4 are each independently a carbon atom, a nitrogen atom, or a sulfur atom.

또한, 본 발명은, Further, according to the present invention,

음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기 전기발광 소자에 있어서, In the organic electroluminescent element in which the organic thin film layer which consists of one layer or multiple layers containing a light emitting layer at least is clamped between a cathode and an anode,

상기 유기 박막층 중 적어도 1층이 본 발명의 디벤조테트라센계 유도체를 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기 전기발광 소자를 제공한다.Provided is an organic electroluminescent device characterized in that at least one of the organic thin film layers contains the dibenzotetracene-based derivative of the present invention alone or in combination of two or more thereof.

또 본 발명에 따른 유기발광화합물 및 이를 이용한 유기 발광소자는 하기 화학식 1 내지 249에 해당하는 유기발광화합물을 기초로 한다.In addition, the organic light emitting compound and the organic light emitting device using the same according to the present invention is based on the organic light emitting compound corresponding to the formula 1 to 249.

본 발명의 디벤조테트라센계 유도체는 기존의 유기 발광 재료보다 발광 효율이 좋고, 재료의 색순도 및 수명특성이 뛰어나다. 또한, 적절한 색좌표를 나타내는 우수한 골격을 갖는다. 따라서, 본 발명의 디벤조테트라센 유도체를 발광재료로서 채용하는 유기 전기발광 소자는 고효율 및 장수명의 특성을 갖는다.The dibenzotetracene-based derivative of the present invention has better luminous efficiency than the conventional organic light emitting material, and excellent color purity and life characteristics of the material. It also has an excellent skeleton exhibiting appropriate color coordinates. Therefore, the organic electroluminescent device employing the dibenzotetracene derivative of the present invention as a light emitting material has characteristics of high efficiency and long life.

이하 본 발명을 상세히 설명하도록 한다.
Hereinafter, the present invention will be described in detail.

본 발명은 다양한 변경을 가할 수 있고 여러 가지 형태를 가질 수 있는 바, 구현예(態樣, aspect)(또는 실시예)들을 본문에 상세하게 설명하고자 한다. 그러나 이는 본 발명을 특정한 개시 형태에 대해 한정하려는 것이 아니며, 본 발명의 사상 및 기술범위에 포함되는 모든 변경, 균등물 내지 대체물을 포함하는 것으로 이해되어야 한다. The present invention may be modified in various ways and may have various forms, and thus embodiments (or embodiments) will be described in detail in the text. However, this is not intended to limit the present invention to the specific form disclosed, it should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.

본 명세서에서 사용한 용어는 단지 특정한 구현예(태양, 態樣, aspect)(또는 실시예)를 설명하기 위해 사용된 것으로, 본 발명을 한정하려는 의도가 아니다. 단수의 표현은 문맥상 명백하게 다르게 뜻하지 않는 한, 복수의 표현을 포함한다. 본 출원에서, ~포함하다~ 또는 ~이루어진다~ 등의 용어는 명세서 상에 기재된 특징, 숫자, 단계, 동작, 구성요소, 부분품 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 숫자, 단계, 동작, 구성요소, 부분품 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다.The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. In the present application, the term " comprising " or " consisting of ", or the like, refers to the presence of a feature, a number, a step, an operation, an element, a component, But do not preclude the presence or addition of one or more other features, integers, steps, operations, components, parts, or combinations thereof.

다르게 정의되지 않는 한, 기술적이거나 과학적인 용어를 포함해서 여기서 사용되는 모든 용어들은 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자에 의해 일반적으로 이해되는 것과 동일한 의미를 가지고 있다. 일반적으로 사용되는 사전에 정의되어 있는 것과 같은 용어들은 관련 기술의 문맥 상 가지는 의미와 일치하는 의미를 가지는 것으로 해석되어야 하며, 본 출원에서 명백하게 정의하지 않는 한, 이상적이거나 과도하게 형식적인 의미로 해석되지 않는다.
Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Terms such as those defined in commonly used dictionaries are to be interpreted as having a meaning consistent with the contextual meaning of the related art and are to be interpreted as either ideal or overly formal in the sense of the present application Do not.

본 발명은 피리도이미다졸(pyridoimidazole)계 유도체를 개발하여 전자수송층(ETM), 발광층 본 발명은,The present invention is to develop a pyridoimidazole-based derivative to electron transport layer (ETM), the light emitting layer The present invention,

하기 화학식F로 표시되는 디벤조테트라센계 유도체에 관한 것이다:It relates to a dibenzotetracene derivative represented by the following formula (F):

[화학식F]Formula F]

Figure pat00040

Figure pat00040

상기 식에서,Where

R1 내지 R3는 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기 이거나;R 1 to R 3 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , or a Si (C 6 H 5 ) 3 group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기이거나;C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , Triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups

Figure pat00041
,
Figure pat00042
,
Figure pat00043
,
Figure pat00044
,
Figure pat00045
,
Figure pat00046
,
Figure pat00047
,
Figure pat00048
및
Figure pat00049
이거나; 또는
Figure pat00041
,
Figure pat00042
,
Figure pat00043
,
Figure pat00044
,
Figure pat00045
,
Figure pat00046
,
Figure pat00047
,
Figure pat00048
And
Figure pat00049
; or

Figure pat00050
이며;
Figure pat00050
;

A 및 B는 각각 독립적으로 C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기 이거나;A and B are each independently C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Or a Si (C 6 H 5 ) 3 group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기 이거나;C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , Triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups

Figure pat00051
,
Figure pat00052
,
Figure pat00053
,
Figure pat00054
,
Figure pat00055
,
Figure pat00056
,
Figure pat00057
,
Figure pat00058
및
Figure pat00059
이거나;
Figure pat00051
,
Figure pat00052
,
Figure pat00053
,
Figure pat00054
,
Figure pat00055
,
Figure pat00056
,
Figure pat00057
,
Figure pat00058
And
Figure pat00059
;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 및 디히드로인돌기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이거나;C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , 30-30 aryl substituted with one or more substituents selected from the group consisting of triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, and dihydroindole group Or a heteroaryl group of 5 to 60;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups

Figure pat00060
,
Figure pat00061
,
Figure pat00062
,
Figure pat00063
,
Figure pat00064
,
Figure pat00065
,
Figure pat00066
, 및
Figure pat00068
로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이거나;
Figure pat00060
,
Figure pat00061
,
Figure pat00062
,
Figure pat00063
,
Figure pat00064
,
Figure pat00065
,
Figure pat00066
, And
Figure pat00068
6 to 30 aryl groups or 5 to 60 heteroaryl groups substituted with one or more substituents selected from the group consisting of;

Figure pat00069
이며;
Figure pat00069
;

상기 Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로, Ar1, Ar2, Ar3 and Ar4 are each independently,

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기 이거나;C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , Triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;

C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups

Figure pat00070
,
Figure pat00071
,
Figure pat00072
,
Figure pat00073
,
Figure pat00074
,
Figure pat00075
,
Figure pat00076
,
Figure pat00077
및
Figure pat00078
이며;
Figure pat00070
,
Figure pat00071
,
Figure pat00072
,
Figure pat00073
,
Figure pat00074
,
Figure pat00075
,
Figure pat00076
,
Figure pat00077
And
Figure pat00078
;

상기 Ar1 및 Ar2, 및 Ar3 및 Ar4는 각각 독립적으로 서로 결합하여 하나 이상의 C1~C5의 알킬기로 치환 또는 비치환된 5원환 내지 8원환의 고리를 형성할 수 있으며;Ar 1 and Ar 2, and Ar 3 and Ar 4 may be each independently bonded to each other to form a 5- to 8-membered ring unsubstituted or substituted with one or more C 1 to C 5 alkyl groups;

상기 R4, R5, R6, R7, R8 및 R9은 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기이며;R4, R5, R6, R7, R8 and R9 are each independently a hydrogen atom, C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, Nitrile, CF 3 , Si (CH 3 ) 3 , or Si (C 6 H 5 ) 3 groups;

상기 X1, X2, X3, X4는 각각 독립적으로 탄소원자, 질소원자 또는 황원자이며;X 1, X 2, X 3 and X 4 are each independently a carbon atom, a nitrogen atom or a sulfur atom;

상기 Y1, Y2, Y3, Y4는 각각 독립적으로 탄소원자, 질소원자 또는 황원자인 것이 바람직하다.
Y1, Y2, Y3 and Y4 are preferably each independently a carbon atom, a nitrogen atom or a sulfur atom.

상기 본 발명의 디벤조테트라센계 유도체에 있어서,In the dibenzotetracene derivative of the present invention,

R1 내지 R3는 각각 독립적으로 수소원자, C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 또는 피리미디닐이거나;R 1 to R 3 are each independently a hydrogen atom, C 1 -C 5 straight or branched chain alkyl, C 1 -C 5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl or pyrimidinyl;

Figure pat00079
이며;
Figure pat00079
;

A 및 B는 각각 독립적으로 C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기 이거나;A and B are each independently C 1 -C 5 straight or branched alkyl, C 1 -C 5 straight or branched alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , or Si (C 6 H 5 ) 3 Or;

C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기 이거나;C1-C5 straight or branched chain alkyl, C1-C5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl And phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, benzopyrenyl, perylene, flu unsubstituted or substituted with one or more substituents selected from the group consisting of pyrimidinyl groups. Orenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzothiazole, carr A bazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;

C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C5 straight or branched chain alkyl, C1-C5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl And pyrimidinyl group substituted or unsubstituted with one or more substituents selected from the group consisting of

Figure pat00080
,
Figure pat00081
,
Figure pat00082
,
Figure pat00083
,
Figure pat00084
,
Figure pat00085
,
Figure pat00086
,
Figure pat00087
및
Figure pat00088
이거나;
Figure pat00080
,
Figure pat00081
,
Figure pat00082
,
Figure pat00083
,
Figure pat00084
,
Figure pat00085
,
Figure pat00086
,
Figure pat00087
And
Figure pat00088
;

C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 및 디히드로인돌기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 또는 페난트레닐기이거나;C1-C5 straight or branched chain alkyl, C1-C5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl And phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, benzopyrenyl, perylene, flu unsubstituted or substituted with one or more substituents selected from the group consisting of pyrimidinyl groups. Orenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzothiazole, carr Phenyl, biphenyl, naphthyl, terphenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of bazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, and dihydroindole group, Or a phenanthrenyl group;

C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C5 straight or branched chain alkyl, C1-C5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl And pyrimidinyl group substituted or unsubstituted with one or more substituents selected from the group consisting of

Figure pat00089
,
Figure pat00090
,
Figure pat00091
,
Figure pat00092
,
Figure pat00093
,
Figure pat00094
,
Figure pat00095
,
Figure pat00096
및
Figure pat00097
로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 또는 페난트레닐기이거나;
Figure pat00089
,
Figure pat00090
,
Figure pat00091
,
Figure pat00092
,
Figure pat00093
,
Figure pat00094
,
Figure pat00095
,
Figure pat00096
And
Figure pat00097
Phenyl, biphenyl, naphthyl, terphenyl, or phenanthrenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of;

Figure pat00098
이며;
Figure pat00098
;

상기 Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로, Ar1, Ar2, Ar3 and Ar4 are each independently,

C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기 이거나;C1-C5 straight or branched chain alkyl, C1-C5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl And phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, benzopyrenyl, perylene, flu unsubstituted or substituted with one or more substituents selected from the group consisting of pyrimidinyl groups. Orenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzothiazole, carr A bazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;

C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된C1-C5 straight or branched chain alkyl, C1-C5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl And pyrimidinyl group substituted or unsubstituted with one or more substituents selected from the group consisting of

Figure pat00099
,
Figure pat00100
,
Figure pat00101
,
Figure pat00102
,
Figure pat00103
,
Figure pat00104
,
Figure pat00105
,
Figure pat00106
및
Figure pat00107
이며;
Figure pat00099
,
Figure pat00100
,
Figure pat00101
,
Figure pat00102
,
Figure pat00103
,
Figure pat00104
,
Figure pat00105
,
Figure pat00106
And
Figure pat00107
;

상기 Ar1 및 Ar2, 및 Ar3 및 Ar4는 각각 독립적으로 서로 결합하여 하나 이상의 C1~C3의 알킬기로 치환 또는 비치환된 5원환 내지 6원환의 고리를 형성할 수 있으며;Ar 1 and Ar 2, and Ar 3 and Ar 4 may be each independently bonded to each other to form a 5- to 6-membered ring unsubstituted or substituted with one or more C 1 to C 3 alkyl groups;

상기 R4, R5, R6, R7, R8 및 R9은 각각 독립적으로 수소원자, C1~C5의 직쇄 또는 분지쇄 알킬, 또는 C1~C5의 직쇄 또는 분지쇄 알콕시기이며;R 4, R 5, R 6, R 7, R 8 and R 9 are each independently a hydrogen atom, C 1 -C 5 straight or branched chain alkyl, or C 1 -C 5 linear or branched alkoxy group;

상기 X1, X2, X3, X4는 각각 독립적으로 탄소원자 또는 질소원자이며;X 1, X 2, X 3 and X 4 are each independently a carbon atom or a nitrogen atom;

상기 Y1, Y2, Y3, Y4는 각각 독립적으로 탄소원자 또는 질소원자인 것이 더욱 바람직하다.
More preferably, Y1, Y2, Y3, and Y4 are each independently a carbon atom or a nitrogen atom.

상기 본 발명의 디벤조테트라센계 유도체에 있어서, C1~C5의 직쇄 또는 분지쇄 알킬기는 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기 또는 t-부틸기 일 수 있으며, C1~C5의 직쇄 또는 분지쇄 알콕시기는 메톡시기, 에톡시기, 프로폭시기, 이소프로폭시기, 부톡시기 또는 t-부톡시기 일 수 있다.
In the dibenzotetracene-based derivative of the present invention, the C1-C5 linear or branched alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or a t-butyl group, a C1-C5 straight chain or Branched-chain alkoxy groups may be methoxy groups, ethoxy groups, propoxy groups, isopropoxy groups, butoxy groups or t-butoxy groups.

본 발명의 디벤조테트라센계 유도체는 유기 전기발광 소자용 재료로서 유용하게 사용될 수 있으며, 특히, 유기 전기발광 소자용 재료 중 발광층 형광 녹색 호스트 화합물, 발광층 형광 녹색 도판트 화합물 및 전자수송층 화합물로서 유용하게 사용될 수 있다.
The dibenzotetracene-based derivative of the present invention can be usefully used as a material for an organic electroluminescent device, and in particular, as a light emitting layer fluorescent green host compound, a light emitting layer fluorescent green dopant compound, and an electron transport layer compound among organic electroluminescent device materials. Can be used.

본 발명의 디벤조테트라센계 유도체는 하기 화학식 1 내지 249의 구조(이하 화학식들에서 '화학식'은 생략하고 숫자만 기재함)를 가질 수 있으나 이에 한정되는 것은 아니다:
The dibenzotetracene-based derivative of the present invention may have a structure represented by Chemical Formulas 1 to 249 (hereinafter, the chemical formulas are omitted and only numbers are shown), but is not limited thereto.

Figure pat00108

Figure pat00108

Figure pat00109
Figure pat00109

Figure pat00110
Figure pat00110

Figure pat00111

Figure pat00111

Figure pat00112

Figure pat00112

Figure pat00113
Figure pat00113

Figure pat00114
Figure pat00114

Figure pat00115
Figure pat00115

Figure pat00116
Figure pat00116

Figure pat00117

Figure pat00117

Figure pat00118

Figure pat00118

Figure pat00119
Figure pat00119

Figure pat00120
Figure pat00120

Figure pat00121

Figure pat00121

Figure pat00122
Figure pat00122

Figure pat00123

Figure pat00123

본 발명은 또한,The present invention also relates to

음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기 전기발광 소자에 있어서, In the organic electroluminescent element in which the organic thin film layer which consists of one layer or multiple layers containing a light emitting layer at least is clamped between a cathode and an anode,

상기 유기 박막층 중 적어도 1층이 본 발명의 디벤조테트라센계 유도체를 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기 전기발광 소자에 관한 것이다.At least 1 layer of the said organic thin film layer is related with the organic electroluminescent element characterized by containing the dibenzo tetracene type derivative of this invention individually by 1 type or in combination of 2 or more types.

상기 디벤조테트라센계 유도체는 상기 유기 박막층 중 발광층에 발광층 형광 녹색 호스트 화합물 또는 발광층 형광 녹색 도판트 화합물로 함유되는 경우에 우수한 특성을 나타낸다.The dibenzotetracene-based derivative exhibits excellent characteristics when the light emitting layer of the organic thin film layer is contained as a light emitting layer fluorescent green host compound or a light emitting layer fluorescent green dopant compound.

또한, 상기 유기 박막층이 전자수송층을 포함하는 경우,In addition, when the organic thin film layer includes an electron transport layer,

상기 디벤조테트라센계 유도체가 상기 전자수송층에 전자수송층 화합물로 함유되는 경우 우수한 특성을 나타낸다.When the dibenzotetracene-based derivative is contained in the electron transport layer as an electron transport layer compound exhibits excellent properties.

상기 유기 전기발광 소자는 The organic electroluminescent device is

양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 가질 수 있다.
The anode, the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron injection layer and the cathode may have a stacked structure in this order.

이하에서, 본 발명의 유기 전기발광 소자에 대하여 예를 들어 설명한다. 그러나, 하기에 예시된 내용이 본 발명의 유기 전기발광 소자를 한정하는 것은 아니다.Hereinafter, the organic electroluminescent element of the present invention will be described by way of example. However, the contents illustrated below do not limit the organic electroluminescent device of the present invention.

본 발명의 유기 전기발광 소자는 양극(정공주입전극), 상기 정공주입층(HIL) 및/또는 정공수송층(HTL), 발광층(EML) 및 음극(전자주입전극)이 순차적으로 적층된 구조를 가질 수 있으며, 바람직하게는, 양극과 발광층 사이에 전자차단층(EBL)을, 그리고 음극과 발광층 사이에 전자수송층(ETL), 전자주입층(EIL) 또는 정공차단층(HBL)을 추가로 포함할 수 있다.The organic electroluminescent device of the present invention has a structure in which an anode (hole injection electrode), the hole injection layer (HIL) and / or a hole transport layer (HTL), an emission layer (EML) and a cathode (electron injection electrode) are sequentially stacked. Preferably, it may further include an electron blocking layer (EBL) between the anode and the light emitting layer, and an electron transport layer (ETL), an electron injection layer (EIL) or a hole blocking layer (HBL) between the cathode and the light emitting layer. Can be.

본 발명에 따른 유기 전기발광 소자의 제조방법으로는, 먼저 기판 표면에 양극용 물질을 통상적인 방법으로 코팅하여 양극을 형성한다. 이때, 사용되는 기판은 투명성, 표면 평활성, 취급 용이성 및 방수성이 우수한 유리기판 또는 투명 플라스틱 기판이 바람직하다. 또한, 양극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등이 사용될 수 있다.In the method of manufacturing an organic electroluminescent device according to the present invention, first, a positive electrode is coated on a surface of a substrate by a conventional method to form a positive electrode. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness. As the material for the positive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity may be used.

다음으로, 상기 양극 표면에 정공주입층(HIL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 정공주입층을 형성한다. 이러한 정공주입층 물질로는 구리프탈로시아닌(CuPc), 4,4',4"-트리스(3-메틸페닐아미노)트리페닐아민(m-MTDATA), 4,4',4"-트리스(3-메틸페닐아미노)페녹시벤젠(m-MTDAPB), 스타버스트(starburst)형 아민류인 4,4',4"-트리(N-카바졸릴)트리페닐아민(TCTA), 4,4',4"-트리스(N-(2-나프틸)-N-페닐아미노)-트리페닐아민(2-TNATA) 또는 이데미츠사(Idemitsu)에서 구입가능한 IDE406을 예로 들 수 있다.Next, a hole injection layer (HIL) material is formed on the surface of the anode by vacuum thermal deposition or spin coating using a conventional method. Examples of such hole injection layer materials include copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4' Amino) phenoxybenzene (m-MTDAPB), starburst type amines such as 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine (TCTA), 4,4' Triphenylamine (2-TNATA) or IDE406 available from Idemitsu, for example.

상기 정공주입층 표면에 정공수송층(HTL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 정공수송층을 형성한다. 이때, 정공수송층 물질은 특별히 제한되지 않으며, 비스(N-(1-나프틸-n-페닐))벤지딘(α-NPD), N,N'-다이(나프탈렌-1-일)-N,N'-다이페닐-벤지딘(NPB) 또는 N,N'-다이페닐-N,N'-비스(3-메틸페닐)-1,1'-다이페닐-4,4'-다이아민(TPD)을 예로 들 수 있다.A hole transport layer (HTL) material is vacuum-deposited or spin coated on the surface of the hole injection layer by a conventional method to form a hole transport layer. At this time, the hole transport material is not particularly limited, bis (N- (1-naphthyl- n-phenyl)) benzine (α-NPD), N, N'-di (naphthalen-1-yl) -N, N '-Diphenyl-benzidine (NPB) or N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-diphenyl-4,4'-diamine (TPD) Can be mentioned.

상기 정공수송층 표면에 발광층(EML) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 발광층을 형성한다. 이때, 사용되는 발광층 물질 중 단독 발광물질 또는 발광 형광 호스트 물질로는 녹색의 경우 본 발명의 디벤조테트라센계 유도체가 바람직하게 사용될 수 있으며, 그 밖에 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3)가 사용될 수 있으며, 청색의 경우 Balq(8-하이드록시퀴놀린베릴륨염), DPVBi(4,4'-비스(2,2-다이페닐에테닐)-1,1'-바이페닐)계열, 스파이로(Spiro)물질, 스파이로-DPVBi(스파이로-4,4'-비스(2,2-다이페닐에테닐)-1,1'-바이페닐), LiPBO(2-(2-벤즈옥사졸릴)-페놀 리튬염), 비스(다이페닐비닐)벤젠, 알루미늄-퀴놀린 금속착체, 이미다졸, 티아졸 및 옥사졸의 금속착체 등이 사용될 수 있다.A light emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal deposition or spin coating using a conventional method. At this time, the dibenzotetracene-based derivative of the present invention may be preferably used as a single light emitting material or a light emitting fluorescent host material in the light emitting layer material, and in addition, tris (8-hydroxyquinolinolato) aluminum ( Alq3) may be used, in the case of blue Balq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl) series, Spiro material, Spiro-DPVBi (Spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxa) Zolyl) -phenol lithium salts), bis (diphenylvinyl) benzene, aluminum-quinoline metal complexes, metal complexes of imidazole, thiazole and oxazole, and the like.

발광층 물질 중 발광 형광 호스트와 함께 사용될 수 있는 형광 도펀트(dopant)의 경우 본 발명의 디벤조테트라센계 유도체가 바람직하게 사용될 수 있으며, 추가적인 형광 도펀트로서 이데미츠사(Idemitsu)에서 구입 가능한 IDE102, IDE105, 인광 도펀트로는 트리스(2-페닐피리딘)이리듐(III)(Ir(ppy)3), 이리듐(III)비스[(4,6-다이플루오로페닐)피리디나토-N,C-2']피콜린산염(FIrpic) (참조문헌[Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084]), 플라티늄(II)옥타에틸포르피린(PtOEP), TBE002(코비온사) 등을 사용할 수 있다.In the case of a fluorescent dopant which can be used together with a luminescent fluorescent host in the light emitting layer material, the dibenzotetracene-based derivative of the present invention may be preferably used, and as an additional fluorescent dopant, IDE102, IDE105, phosphorescent, available from Idemitsu Co., Ltd. Dopants include tris (2-phenylpyridine) iridium (III) (Ir (ppy) 3), iridium (III) bis [(4,6-difluorophenyl) pyridinato-N, C-2 '] pi Choline (FIrpic) (Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084), platinum (II) octaethyl porphyrin (PtOEP), TBE002 (Kobiion), etc. Can be used.

상기 발광층 표면에 전자수송층(ETL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 전자수송층을 형성한다. 이때, 사용되는 전자수송층 물질로는 본 발명의 디벤조테트라센계 유도체가 바람직하게 사용될 수 있으며, 그 밖에 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3) 등을 사용할 수 있다.An electron transport layer (ETL) material is formed on the surface of the light emitting layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the dibenzotetracene-based derivative of the present invention may be preferably used as the electron transport layer material, and tris (8-hydroxyquinolinolato) aluminum (Alq3) may be used.

선택적으로는, 발광층과 전자수송층 사이에 정공차단층(HBL)을 추가로 형성하고 발광층에 인광 도펀트를 함께 사용함으로써, 삼중항 여기자 또는 정공이 전자수송층으로 확산되는 현상을 방지할 수 있다. Alternatively, by further forming a hole blocking layer (HBL) between the light emitting layer and the electron transporting layer and using a phosphorescent dopant together with the light emitting layer, it is possible to prevent the phenomenon that the triplet excitons or holes are diffused into the electron transporting layer.

정공차단층의 형성은 정공차단층 물질을 통상적인 방법으로 진공 열증착 및 스핀 코팅하여 실시할 수 있으며, 정공차단층 물질의 경우 특별히 제한되지는 않으나, 바람직하게는 (8-하이드록시퀴놀리놀라토)리튬(Liq), 비스(8-하이드록시-2-메틸퀴놀리놀나토)-알루미늄비페녹사이드(BAlq), 바쏘쿠프로인 (bathocuproine, BCP) 및 LiF 등을 사용할 수 있다.The hole blocking layer can be formed by vacuum thermal deposition and spin coating using a hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, there is no particular limitation, but (8-hydroxyquinolinolato Lithium biphenoxide (BAlq), bathocuproine (BCP), LiF, etc. may be used as the lithium salt (Li), bis (8-hydroxy-2-methylquinolinonato)

상기 전자수송층 표면에 전자주입층(EIL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 전자주입층을 형성한다. 이때, 사용되는 전자주입층 물질의 경우 특별히 제한되지 않으며, 바람직하게는 LiF, Liq, Li2O, BaO, NaCl, CsF 등의 물질을 사용할 수 있다.An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the material of the electron injection layer to be used is not particularly limited, and preferably materials such as LiF, Liq, Li2O, BaO, NaCl, and CsF can be used.

마지막으로, 상기 전자주입층 표면에 음극용 물질을 통상적인 방법으로 진공 열증착하여 음극을 형성한다.Finally, a negative electrode is formed on the surface of the electron injecting layer by vacuum thermal deposition using a conventional method.

이때, 사용되는 음극용 물질로는 리튬(Li), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘(Mg), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등이 사용될 수 있다. 또한, 전면발광 유기 전기발광 소자의 경우 산화인듐주석(ITO) 또는 산화인듐아연(IZO)를 사용하여 빛이 투과할 수 있는 투명한 음극을 형성할 수도 있다.At this time, as the negative electrode material to be used, lithium, aluminum, aluminum-lithium, calcium, magnesium, (Mg-Ag) or the like may be used. In the case of the front emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass.

본 발명에 따른 유기 전계발광 소자는 상술한 바와 같은 순서, 즉 양극/정공주입층/정공수송층/발광층/정공차단층/전자수송층/전자주입층/음극 순으로 제조하여도 되고, 그 반대로 음극/전자주입층/전자수송층/정공차단층/발광층/정공수송층/정공주입층/양극의 순서로 제조하여도 무방하다.
The organic electroluminescent device according to the present invention may be manufactured in the same order as described above, that is, in the order of anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode, and vice versa. The electron injection layer, the electron transport layer, the hole blocking layer, the light emitting layer, the hole transport layer, the hole injection layer and the anode may be manufactured in the order.

이하에서, 본 발명의 화합물들의 합성방법을 대표적인 예를 들어 하기에 설명한다. 그러나, 본 발명의 화합물들의 합성방법이 하기 예시된 방법으로 한정되는 것은 아니며, 본 발명의 화합물들은 하기에 예시된 방법과 이 분야의 공지의 방법에 의해 제조될 수 있다.
Hereinafter, a method for synthesizing the compounds of the present invention will be described below with a representative example. However, the method of synthesizing the compounds of the present invention is not limited to the methods illustrated below, and the compounds of the present invention may be prepared by the methods illustrated below and methods known in the art.

화합물 [6]의 합성Synthesis of Compound [6]

[반응식 1] [Reaction Scheme 1]

Figure pat00124

Figure pat00124

중간체 화합물 [1-1]의 제조Preparation of intermediate compound [1-1]

1L 3구 플라스크에 무수푸탈산32.4g(0.219mol)과 알루미늄클로라이드 43.8g(0.328mol)를 디클로로메탄 1L에서 현탁교반시키고 상온 질소분위기에서 트리페닐렌50g(0.219mol)을 첨가한다. 상온에서 2시간 교반후 디클로로메탄과 1N 염산 수용액으로 추출한다. 유기층을 분리하여 무수황산 마그네슘으로 건조 후 여과하여 얻은 유기층을 감압농축 후 디클로로메탄과 헥산으로 재결정화하여 흰색 고체의 중간체 화합물 [1-1] 68g(82%)을 수득하였다.Into a 1 L three-neck flask, 3.4 g (0.219 mol) of phthalic anhydride and 43.8 g (0.328 mol) of aluminum chloride are suspended and stirred in 1 L of dichloromethane, and 50 g (0.219 mol) of triphenylene are added in a room temperature nitrogen atmosphere. After stirring for 2 hours at room temperature and extracted with dichloromethane and 1N hydrochloric acid aqueous solution. The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered. The organic layer was concentrated under reduced pressure, and then recrystallized with dichloromethane and hexane to obtain 68 g (82%) of an intermediate compound [1-1] as a white solid.

중간체화합물 [1-2]의 제조Preparation of Intermediate Compound [1-2]

중간체 화합물[1-1] 68g(0.18mol)을 메탄 술폰산 500mL 로 약 110℃에서 10시간 동안 교반후 상온으로 냉가한다. 반응액을 물 3L에 부어 고체화시킨다. 갈색고체를 디클로로메탄과 메탄올로 재결정화하고 컬럼크로마토그라프로 분리정제하여 노란색 고체의 중간체화합물 [1-2] 33g(51%)을 수득하였다.
68 g (0.18 mol) of an intermediate compound [1-1] were stirred with 500 mL of methane sulfonic acid at about 110 ° C. for 10 hours, and then cooled to room temperature. The reaction solution is poured into 3 L of water to solidify. The brown solid was recrystallized from dichloromethane and methanol and purified by column chromatography to give 33g (51%) of the intermediate compound [1-2] as a yellow solid.

화합물[6]의 제조Preparation of Compound [6]

250mL 삼구 반응플라스크에 브로모벤젠 5.2g(33.48mmol) 을 무수테트라히드로퓨란 100mL로 -78℃에서 교반시킨다. n-부틸리튬(2.5M in hexane) 13.4mL(33.48mmol)를 동온도에서 적가시키고 30분 후에 중간체화합물 [1-2] 5.0g(13.95mmol)을 고체로 첨가시킨다. 반응온도를 상온까지 서서히 6시간 동안 올리고 에틸아세테이트와 포화암모늄 수용액으로 추출한다. 유기층을 감압 농축 후 아세트산 100mL로 교반한다. 반응액에 요오드화 칼륨3.47g(20.93mmol) 치아인산나트륨 1수화물4.43g(41.85mmol)을 첨가하여 6시간 환류교반시킨다. 반응온도를 상온으로 냉각시키고 생성된 고체를 여과한다. 디클로로메탄과 메탄올로 재결정화하여 연두빛 노란색고체의 목적화합물[6] 2.9g(44%)을 수득하였다.
In a 250 mL three-necked reaction flask, 5.2 g (33.48 mmol) of bromobenzene were stirred with 100 mL of anhydrous tetrahydrofuran at -78 ° C. 13.4 mL (33.48 mmol) of n-butyllithium (2.5 M in hexane) is added dropwise at the same temperature, and after 30 minutes, 5.0 g (13.95 mmol) of the intermediate compound [1-2] are added as a solid. The reaction temperature was gradually raised to room temperature for 6 hours and extracted with ethyl acetate and saturated aqueous ammonium solution. The organic layer was concentrated under reduced pressure and stirred with 100 mL of acetic acid. 3.47 g (20.93 mmol) of potassium iodide sodium phosphate monohydrate (4.43 g (41.85 mmol)) was added to the reaction solution, and the mixture was stirred under reflux for 6 hours. Cool the reaction temperature to room temperature and filter the resulting solid. Recrystallization from dichloromethane and methanol afforded 2.9 g (44%) of the title compound [6] as a light yellowish yellow solid.

(2) 화합물 [71]의 합성(2) Synthesis of Compound [71]

[반응식 2] [Reaction Scheme 2]

Figure pat00125

Figure pat00125

중간체 화합물 [71-1]의 제조Preparation of Intermediate Compound [71-1]

1L 플라스크에 중간체 화합물 [1-1] 40g (0.106mol), 아연 분말 69.5g(1.06mol), 수산화나트륨42.5g(1.06mol)을 투입하고 디에틸렌글리콜 800mL 로 150℃에서 12시간 동안 교반한다. 반응온도를 상온으로 냉각 후 규조토에 여과한다. 여과액을 1N 염산 수용액으로 산성화시켜 고체 여과한다. 컬럼크로마토그라프로 분리 정제하여 흰색 고체의 중간체 화합물[71-1] 31.6g(82%)을 수득하였다.
40 g (0.106 mol) of intermediate compound [1-1], zinc powder 69.5 g (1.06 mol), and sodium hydroxide 42.5 g (1.06 mol) were added to a 1 L flask, and the mixture was stirred with 800 mL of diethylene glycol at 150 ° C. for 12 hours. The reaction temperature is cooled to room temperature and then filtered through diatomaceous earth. The filtrate is acidified with 1N aqueous hydrochloric acid solution and filtered solid. Separation and purification by column chromatography gave 31.6 g (82%) of an intermediate compound [71-1] as a white solid.

중간체화합물 [71-2]의 제조Preparation of Intermediate Compound [71-2]

중간체 화합물[71-1] 31g(85.53mmol)을 메탄 술폰산 500mL 로 약 60℃에서 6시간 동안 교반후 상온으로 냉가한다. 반응액을 물 1L에 부어 고체화시킨다. 갈색고체를 디클로로메탄과 메탄올로 재결정화하고 컬럼크로마토그라프로 분리정제하여 미색 고체의 중간체화합물 [71-2] 19.7g(67%)을 수득하였다.
31 g (85.53 mmol) of the intermediate compound [71-1] were stirred with 500 mL of methane sulfonic acid at about 60 ° C. for 6 hours, and then cooled to room temperature. The reaction solution is poured into 1 L of water and solidified. The brown solid was recrystallized from dichloromethane and methanol and purified by column chromatography to give 19.7 g (67%) of an intermediate compound [71-2] as an off-white solid.

중간체화합물 [71-3]의 제조Preparation of Intermediate Compound [71-3]

250mL 삼구 반응플라스크에 브로모벤젠 2.73g(17.42mmol), 마그네슘 0.42g (17.42mmol)을 투입하고 질소 분위기에서 2시간 환류교반시킨다. 반응액을 상온으로 냉각시키고 중간체 화합물 [71-2] 5.0g (14.51mmol)을 첨가시킨다. 반응온도를 승온하여 12시간 동안 환류 교반시킨다. 상온으로 냉각하여 반응액을 1N 염산 수용액에 붓고 에틸아세테이트로 추출한다. 유기층 분리 후 디클로로메탄과 메탄올로 재결정화하여 노란색 고체의 중간체 화합물 [71-3] 4.5g(78%)을 수득하였다.
2.73 g (17.42 mmol) of bromobenzene and 0.42 g (17.42 mmol) of magnesium were added to a 250 mL three-neck reaction flask and stirred under reflux for 2 hours in a nitrogen atmosphere. The reaction solution is cooled to room temperature and 5.0 g (14.51 mmol) of the intermediate compound [71-2] are added. The reaction temperature is raised and refluxed for 12 hours. After cooling to room temperature, the reaction mixture was poured into 1N aqueous hydrochloric acid solution and extracted with ethyl acetate. After separation of the organic layer, recrystallization with dichloromethane and methanol yielded 4.5 g (78%) of an intermediate compound [71-3] as a yellow solid.

중간체 화합물 [71-4]의 제조Preparation of Intermediate Compound [71-4]

250mL 삼구 반응플라스크에 중간체 화합물 [71-3] 4.5g (11.12mmol), N-브로모석시니미드2.2g (9.74mmol)을 차광하여 디메틸포름아미드 100mL 로 5시간 동안 교반한다. 반응액을 정제수에 부어 고체화 시킨다. 고체를 여과하고 디클로로메탄과 메탄올로 재결정화하여 노란색 고체의 중간체 화합물 [71-4] 3.9g(74%)을 수득하였다.
4.5 g (11.12 mmol) of the intermediate compound [71-3] and 2.2 g (9.74 mmol) of N-bromosuccinimide were shielded from a 250 mL three-neck reaction flask and stirred with 100 mL of dimethylformamide for 5 hours. The reaction solution is poured into purified water to solidify. The solid was filtered and recrystallized with dichloromethane and methanol to yield 3.9 g (74%) of the intermediate compound [71-4] as a yellow solid.

화합물 [71]의 제조Preparation of Compound [71]

250mL삼구 반응플라스크에 중간체 화합물 [71-4]] 3.9g (8.06mmol), 1-나프틸보론산1.66g (9.68mmol), 테트라키스(트리페닐포스핀)팔라듐 0.1g(0.08mmol), 탄산칼륨 (K2CO3) 1.56g (11.29mmol) 을 투입하고 질소기류하에서 1,4-디옥산100mL , 정제수 10mL 로 12시간 동안 환류 교반시킨다. 반응종결 후 실온까지 천천히 냉각한 다음 반응액을 여과한다. 여과된 고체는 정제수 와 메탄올로 세척하고 디클로로메탄과 메탄올로 재결정화하여 노란색 고체의 화합물[71] 2.6g(61%)를 수득하였다.
3.9 g (8.06 mmol) of the intermediate compound [71-4]], 1-naphthyl boronic acid 1.66 g (9.68 mmol) in a 250 mL three-neck reaction flask, 0.1 g (0.08 mmol) of tetrakis (triphenylphosphine) palladium, carbonic acid 1.56 g (11.29 mmol) of potassium (K 2 CO 3 ) was added thereto, and the mixture was stirred under reflux for 12 hours with 100 mL of 1,4-dioxane and 10 mL of purified water. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid was washed with purified water and methanol and recrystallized with dichloromethane and methanol to give 2.6g (61%) of the compound [71] as a yellow solid.

(3) 화합물 [199]의 합성(3) Synthesis of Compound [199]

[반응식 3] Scheme 3

Figure pat00126

Figure pat00126

중간체화합물 [199-1]의 제조Preparation of Intermediate Compound [199-1]

1L 3구 플라스크에 2-브로모무수푸탈산29.8g(0.131mol)과 알루미늄클로라이드26.3g(0.197mol)를 디클로로메탄 1L에서 현탁교반시키고 상온 질소분위기에서 트리페닐렌30g(0.131mol)을 첨가한다. 상온에서 2시간 교반후 디클로로메탄과 1N 염산 수용액으로 추출한다. 유기층을 분리하여 무수황산 마그네슘으로 건조 후 여과하여 얻은 유기층을 감압농축 후 디클로로메탄과 헥산으로 재결정화하여 흰색 고체의 중간체 화합물 [199-1] 46g(77%)을 수득하였다.To a 1 L three-necked flask, 29.8 g (0.131 mol) of 2-bromophthalic anhydride and 26.3 g (0.197 mol) of aluminum chloride are suspended and stirred in 1 L of dichloromethane and 30 g (0.131 mol) of triphenylene are added in a nitrogen atmosphere at room temperature. . After stirring for 2 hours at room temperature and extracted with dichloromethane and 1N hydrochloric acid aqueous solution. The organic layer was separated, dried over anhydrous magnesium sulfate, and then filtered. The organic layer was concentrated under reduced pressure and recrystallized with dichloromethane and hexane to obtain 46 g (77%) of an intermediate compound [199-1].

중간체화합물 [199-2]의 제조Preparation of Intermediate Compound [199-2]

중간체 화합물[199-1] 45g(98.8mmol)을 메탄 술폰산 500mL 로 약 110℃에서 10시간 동안 교반후 상온으로 냉가한다. 반응액을 물 3L에 부어 고체화시킨다. 갈색고체를 디클로로메탄과 메탄올로 재결정화하고 컬럼크로마토그라프로 분리정제하여 노란색 고체의 중간체화합물 [199-2] 19g(44%)을 수득하였다.
45 g (98.8 mmol) of an intermediate compound [199-1] were stirred with 500 mL of methane sulfonic acid at about 110 ° C. for 10 hours, and then cooled to room temperature. The reaction solution is poured into 3 L of water to solidify. The brown solid was recrystallized from dichloromethane and methanol and purified by column chromatography to give 19g (44%) of the intermediate compound [199-2] as a yellow solid.

중간체화합물 [199-3]의 제조Preparation of Intermediate Compound [199-3]

500mL삼구 반응플라스크에 중간체 화합물 [199-2] 10.0g (22.87mmol), 페닐보론산3.35g (27.44mmol), 테트라키스(트리페닐포스핀)팔라듐 0.26g(0.23mmol), 탄산칼륨 (K2CO3)4.42g (32.01mmol), 을 투입하고 질소기류하에서 1,4-디옥산200mL , 정제수 20mL 로 12시간 동안 환류 교반시킨다. 반응종결 후 실온까지 천천히 냉각한 다음 반응액을 여과한다. 여과된 고체는 정제수와 메탄올로 세척하여 노란색 고체의 중간체 화합물[199-3] 7.25g(73%)를 수득하였다.
10.0 g (22.87 mmol) of the intermediate compound [199-2], phenyl boronic acid 3.35 g (27.44 mmol), tetrakis (triphenylphosphine) palladium 0.26 g (0.23 mmol), potassium carbonate (K 2 ) in a 500 mL three-neck reaction flask. CO 3 ) 4.42g (32.01mmol) was added thereto, and the mixture was stirred under reflux with 200 mL of 1,4-dioxane and 20 mL of purified water for 12 hours under a nitrogen stream. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid was washed with purified water and methanol to yield 7.25 g (73%) of an intermediate compound [199-3] as a yellow solid.

화합물[199]의 제조Preparation of Compound [199]

250mL 삼구 반응플라스크에 브로모벤젠 4.3g(27.62mmol) 을 무수테트라히드로퓨란 100mL로 -78℃에서 교반시킨다. n-부틸리튬(2.5M in hexane) 11.1mL(27.62mmol)를 동온도에서 적가시키고 30분 후에 중간체화합물 [199-3] 5.0g(11.51mmol)을 고체로 첨가시킨다. 반응온도를 상온까지 서서히 6시간 동안 올리고 에틸아세테이트와 포화암모늄 수용액으로 추출한다. 유기층을 감압 농축 후 아세트산 100mL로 교반한다. 반응액에 요오드화 칼륨3.82g(23.02mmol) 치아인산나트륨 1수화물4.88g(46.03mmol)을 첨가하여 6시간 환류교반시킨다. 반응온도를 상온으로 냉각시키고 생성된 고체를 여과한다. 디클로로메탄과 메탄올로 재결정화하여 연두빛 노란색고체의 목적화합물[199] 3.0g(47%)을 수득하였다.
In a 250 mL three-necked reaction flask, 4.3 g (27.62 mmol) of bromobenzene were stirred with 100 mL of anhydrous tetrahydrofuran at -78 ° C. 11.1 mL (27.62 mmol) of n-butyllithium (2.5 M in hexane) is added dropwise at the same temperature, and after 30 minutes, 5.0 g (11.51 mmol) of the intermediate compound are added as a solid. The reaction temperature was gradually raised to room temperature for 6 hours and extracted with ethyl acetate and saturated aqueous ammonium solution. The organic layer was concentrated under reduced pressure and stirred with 100 mL of acetic acid. 4.88 g (46.03 mmol) of potassium iodide sodium phosphate monohydrate was added to the reaction solution, and the mixture was stirred under reflux for 6 hours. Cool the reaction temperature to room temperature and filter the resulting solid. Recrystallization from dichloromethane and methanol afforded 3.0 g (47%) of the title compound [199] as a light yellow solid.

(4) 화합물 [206]의 합성(4) Synthesis of Compound [206]

[반응 예 4] [Reaction Example 4]

Figure pat00127
Figure pat00127

중간체 화합물 [206-1]의 제조Preparation of Intermediate Compound [206-1]

중간체 화합물 [71-2] 30.0g(87.1mmol)을 이소프로판올 0.5L로 현탁 교반시킨다. 상온에서 소디움보로하이드라이드 8.2g(217.8mmol)을 천천히 첨가시킨다. 반응 온도를 승온하여 6시간 동안 환류 교반시킨다. 상온으로 냉각 후 1N 염산 수용액 2L에 아주 천천히 붓는다. 오렌지 고체를 여과하고 메탄올로 세척한다. 고체를 디클로로메탄과 메탄올로 재결정화하여 미색고체의 중간체 화합물 [206-1] 23.1g(81%)을 수득하였다.
30.0 g (87.1 mmol) of the intermediate compound [71-2] are suspended and stirred with 0.5 L of isopropanol. Slowly add 8.2 g (217.8 mmol) of sodium borohydride at room temperature. The reaction temperature is raised to reflux and stir for 6 hours. After cooling to room temperature, very slowly pour into 2L of 1N aqueous hydrochloric acid solution. The orange solid is filtered off and washed with methanol. The solid was recrystallized from dichloromethane and methanol to give 23.1 g (81%) of an off-white solid compound [206-1].

중간체 화합물 [206-2]의 제조Preparation of Intermediate Compound [206-2]

반응예 2와 동일한 방법으로 중간체 화합물[535-1](23g), N-브로모석시니미드(2.2당량), 디메틸포름아미드를 사용하여 노란색 고체의 중간체 화합물 [206-2] 26.2g(77%)을 수득하였다.
26.2 g (77%) of an intermediate compound [206-2] as an intermediate compound [535-1] (23 g), N-bromosuccinimide (2.2 equivalents) and dimethylformamide in the same manner as in reaction example 2 ) Was obtained.

화합물 [206]의 제조Preparation of Compound [206]

250mL 반응플라스크에 중간체 화합물 [206-2] 3.0g (6.17mmol), 디페닐아민 2.3g(13.57mmol), 팔라듐(II)아세테이트 14mg(0.06mmol), 트리터트부틸포스핀(50%) 0.03mL(0.12mmol), 터트부톡시 나트륨 1.42g (14.81mmol)을 투입하고 질소기류하에서 톨루엔100mL로 12시간 동안 환류 교반시킨다. 반응종결 후 실온까지 천천히 냉각한 다음 반응액을 포화 염화암모늄 수용액에 붓고 에틸아세테이트로 추출한다. 유기층을 분리하고 무수황산 마그네슘으로 건조하여 여과한다. 여과액은 감압농축하고 컬럼크로마토그라프로 분리정제하여 노란색고체의 목적화합물[206] 2.3g(58%)를 수득하였다.
3.0 g (6.17 mmol) of intermediate compound [206-2], 2.3 g (13.57 mmol) of diphenylamine, 14 mg (0.06 mmol) of palladium (II) acetate, 0.03 mL of tritertbutyl phosphine (50%) in a 250 mL reaction flask (0.12 mmol) and 1.42 g (14.81 mmol) of tert-butoxy sodium were added thereto, and the mixture was stirred under reflux for 12 hours with 100 mL of toluene under a nitrogen stream. After completion of the reaction, the mixture was slowly cooled to room temperature, and the reaction solution was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer is separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to give 2.3 g (58%) of the title compound [206] as a yellow solid.

합성예 1~249: 디벤조테트라센계 유도체의 합성 Synthesis Examples 1 to 249: Synthesis of Dibenzotetracene Derivative

상기 반응예 1 내지 반응예 4의 방법에 따라, 본 발명의 화합물 1 내지 431의 화합물을 제조하였으며, 하기 [합성예]에 그 확인 결과를 나타내었다
According to the method of Reaction Examples 1 to 4, the compounds of Compounds 1 to 431 of the present invention were prepared, and the results are shown in the following Synthesis Examples.

[합성예 1] 화합물 [1]의 합성[Synthesis Example 1] Synthesis of compound [1]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(d, 2H), 2.54(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (d, 2H), 2.54 (s, 6H)

MS/FAB: 356(M+)MS / FAB: 356 (M + )

[합성예 2] 화합물 [2]의 합성[Synthesis Example 2] Synthesis of compound [2]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(d, 2H), 2.77(m, 2H), 1.23(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (d, 2H), 2.77 (m, 2 H), 1.23 (s, 12 H)

MS/FAB: 412(M+)
MS / FAB: 412 (M + )

[합성예 3] 화합물 [3]의 합성[Synthesis Example 3] Synthesis of compound [3]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(d, 2H), 1.38(s, 18H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (d, 2H), 1.38 (s, 18 H)

MS/FAB: 440(M+)
MS / FAB: 440 (M + )

[합성예 4] 화합물 [4]의 합성[Synthesis Example 4] Synthesis of compound [4]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(d, 2H), 0.15(s, 18H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (d, 2H), 0.15 (s, 18 H)

MS/FAB: 472(M+)
MS / FAB: 472 (M + )

[합성예 5] 화합물 [5]의 합성[Synthesis Example 5] Synthesis of compound [5]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (d, 2H)

MS/FAB: 464(M+)
MS / FAB: 464 (M + )

[합성예 6] 화합물 [6]의 합성[Synthesis Example 6] Synthesis of compound [6]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.42~7.29(m, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.42-7.29 (m, 12H)

MS/FAB: 480(M+)
MS / FAB: 480 (M + )

[합성예 7] 화합물 [7]의 합성[Synthesis Example 7] Synthesis of compound [7]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29~7.21(m, 10H), 2.24(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81 ~ 7.72 (m, 6H), 7.29 ~ 7.21 (m, 10H) , 2.24 (s, 6H)

MS/FAB: 508(M+)
MS / FAB: 508 (M + )

[합성예8] 화합물 [8]의 합성Synthesis Example 8 Synthesis of Compound [8]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.79(m, 8H), 7.29~7.23(m, 6H), 7.09(d, 2H), 2.24(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.79 (m, 8H), 7.29-7.33 (m, 6H) , 7.09 (d, 2H), 2.24 (s, 6H)

MS/FAB: 508(M+)
MS / FAB: 508 (M + )

[합성예 9] 화합물 [9]의 합성[Synthesis Example 9] Synthesis of compound [9]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.57(s, 2H), 7.29~7.19(m, 8H), 2.22(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.57 (s, 2H), 7.29 ~ 7.19 (m, 8H), 2.22 (s, 6H)

MS/FAB: 508(M+)
MS / FAB: 508 (M + )

[합성예 10] 화합물 [10]의 합성[Synthesis Example 10] Synthesis of Compound [10]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.22(d, 2H), 8.01~7.92(m, 6H), 7.77(s, 2H), 7.49(d, 2H), 7.27~7.24(m, 4H), 2.44(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.22 (d, 2H), 8.01-7.82 (m, 6H), 7.77 (s, 2H), 7.49 (d, 2H), 7.27-7.44 (m, 4H), 2.44 (s, 12H)

MS/FAB: 536(M+)
MS / FAB: 536 (M + )

[합성예 11] 화합물 [11]의 합성[Synthesis Example 11] Synthesis of compound [11]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.22(d, 2H), 8.01~7.92(m, 6H), 7.65(d, 2H), 7.49(d, 2H), 7.26~7.20(m, 4H), 2.69(2, 6H), 2.44(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.22 (d, 2H), 8.01-7.82 (m, 6H), 7.65 (d, 2H), 7.49 (d, 2H), 7.26-7.20 (m, 4H), 2.69 (2, 6H), 2.44 (s, 6H)

MS/FAB: 536(M+)
MS / FAB: 536 (M + )

[합성예 12] 화합물 [12]의 합성[Synthesis Example 12] Synthesis of compound [12]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.22(d, 2H), 8.01~7.92(m, 6H), 7.70(s, 4H), 7.49(d, 2H), 7.41(s, 2H), 2.44(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.22 (d, 2H), 8.01-7.82 (m, 6H), 7.70 (s, 4H), 7.49 (d, 2H), 7.41 (s, 2H), 2.44 (s, 12H)

MS/FAB: 536(M+)
MS / FAB: 536 (M + )

[합성예 13] 화합물 [13]의 합성[Synthesis Example 13] Synthesis of compound [13]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.22(d, 2H), 8.01~7.92(m, 6H), 7.49~7.47(m, 10H), 1.15(s, 18H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.22 (d, 2H), 8.01 ~ 7.92 (m, 6H), 7.49 ~ 7.47 (m, 10H) , 1.15 (s, 18H)

MS/FAB: 592(M+)
MS / FAB: 592 (M + )

[합성예 14] 화합물 [14]의 합성[Synthesis Example 14] Synthesis of compound [14]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.22(d, 2H), 8.01~7.87(m, 10H), 7.56~7.49(m, 6H), 0.35(s, 18H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.22 (d, 2H), 8.01-7.87 (m, 10H), 7.56-7.49 (m, 6H) , 0.35 (s, 18H)

MS/FAB: 624(M+)
MS / FAB: 624 (M + )

[합성예 15] 화합물 [15]의 합성[Synthesis Example 15] Synthesis of compound [15]

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.01~7.92(m, 6H), 7.49~7.40(m, 10H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.01 ~ 7.92 (m, 6H), 7.49 ~ 7.40 (m, 10H)

MS/FAB: 516(M+)
MS / FAB: 516 (M + )

[합성예 16] 화합물 [16]의 합성[Synthesis Example 16] Synthesis of compound [16]

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.01~7.92(m, 14H), 7.49(s, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.01 ~ 7.92 (m, 14H), 7.49 (s, 2H)

MS/FAB: 530(M+)
MS / FAB: 530 (M + )

[합성예 17] 화합물 [17]의 합성[Synthesis Example 17] Synthesis of Compound [17]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 1H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.58(d, 4H), 7.29~7.28(m, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 1H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.58 (d, 4H), 7.29 ~ 7.28 (m, 6H)

MS/FAB: 616(M+)
MS / FAB: 616 (M + )

[합성예 18] 화합물 [18]의 합성[Synthesis Example 18] Synthesis of Compound [18]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.78(10H), 7.45~7.27(m, 36H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.78 (10H), 7.45-7.27 (m, 36H)

MS/FAB: 997(M+)
MS / FAB: 997 (M + )

[합성예 19] 화합물 [19]의 합성[Synthesis Example 19] Synthesis of Compound [19]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.45(d, 2H), 8.32(d, 2H), 8.21(s, 1H), 8.02~7.94(m, 6H), 7.81~7.72(m, 6H), 7.51~7.45(m, 6H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.45 (d, 2H), 8.32 (d, 2H), 8.21 (s, 1H), 8.02 to 7.94 (m, 6H), 7.81 ~ 7.72 (m, 6H), 7.51-7.45 (m, 6H), 7.29 (t, 2H)

MS/FAB: 580(M+)
MS / FAB: 580 (M + )

[합성예 20] 화합물 [20]의 합성[Synthesis Example 20] Synthesis of compound [20]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 1H), 8.02(d, 2H), 7.90~7.63(m, 14H), 7.49~7.48(m, 6H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 1H), 8.02 (d, 2H), 7.90-7.63 (m, 14H), 7.49-7.48 (m, 6H) , 7.29 (t, 2 H)

MS/FAB: 580(M+)
MS / FAB: 580 (M + )

[합성예 21] 화합물 [21]의 합성[Synthesis Example 21] Synthesis of Compound [21]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.42~7.41(m, 8H), 7.31~7.29(m, 4H), 7.15(d, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.42-7.41 (m, 8H) , 7.31-7.29 (m, 4H), 7.15 (d, 8H)

MS/FAB: 632(M+)
MS / FAB: 632 (M + )

[합성예 22] 화합물 [22]의 합성[Synthesis Example 22] Synthesis of compound [22]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.60(s, 2H), 7.47~7.29(m, 18H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.60 (s, 2H), 7.47 ~ 7.29 (m, 18H)

MS/FAB: 632(M+)
MS / FAB: 632 (M + )

[합성예 23] 화합물 [23]의 합성[Synthesis Example 23] Synthesis of compound [23]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.69(m, 14H), 7.41~7.29(m, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.69 (m, 14H), 7.41-7.29 (m, 12H)

MS/FAB: 632(M+)
MS / FAB: 632 (M + )

[합성예 24] 화합물 [24]의 합성[Synthesis Example 24] Synthesis of compound [24]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.56(s, 6H), 7.42~7.41(m, 16H), 7.31~7.29(m, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.56 (s, 6H), 7.42 ~ 7.41 (m, 16H), 7.31-7.29 (m, 6H)

MS/FAB: 784(M+)
MS / FAB: 784 (M + )

[합성예 25] 화합물 [25]의 합성[Synthesis Example 25] Synthesis of compound [25]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.66(m, 18H), 7.41~7.41(t, 8H), 7.31~7.29(m, 6H), 7.11(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.62 (m, 18H), 7.41-7.41 (t, 8H) , 7.31-7.29 (m, 6H), 7.11 (d, 2H)

MS/FAB: 784(M+)
MS / FAB: 784 (M + )

[합성예 26] 화합물 [26]의 합성[Synthesis Example 26] Synthesis of compound [26]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 1H), 8.02(d, 2H), 7.83~7.67(m, 12H), 7.53(d, 2H), 7.45(d, 2H), 7.29~7.28(m, 4H), 7.18(t, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 1H), 8.02 (d, 2H), 7.83-7.67 (m, 12H), 7.53 (d, 2H), 7.45 (d, 2H), 7.29-7.28 (m, 4H), 7.18 (t, 2H), 1.62 (s, 12H)

MS/FAB: 712(M+)
MS / FAB: 712 (M + )

[합성예 27] 화합물 [27]의 합성[Synthesis Example 27] Synthesis of compound [27]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.96(s, 2H), 7.81~7.72(m, 8H), 7.51(d, 2H), 7.45~7.43(m, 4H), 7.29~7.28(m, 4H), 7.18(t, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.96 (s, 2H), 7.81 ~ 7.72 (m, 8H), 7.51 (d, 2H), 7.45-7.43 (m, 4H), 7.29-7.28 (m, 4H), 7.18 (t, 2H), 1.62 (s, 12H)

MS/FAB: 712(M+)
MS / FAB: 712 (M + )

[합성예 28] 화합물 [28]의 합성[Synthesis Example 28] Synthesis of compound [28]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.85~7.72(m, 12H), 7.51(t, 2H), 7.42(d, 2H), 7.29~7.23(m, 6H), 0.56(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.85 ~ 7.72 (m, 12H), 7.51 (t, 2H), 7.42 (d, 2H), 7.29-7.33 (m, 6H), 0.56 (s, 12H)

MS/FAB: 745(M+)
MS / FAB: 745 (M + )

[합성예 29] 화합물 [29]의 합성[Synthesis Example 29] Synthesis of compound [29]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.35(d, 2H), 8.21(s, 2H), 8.02~7.72(m, 16H), 7.42~7.40(m, 4H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.35 (d, 2H), 8.21 (s, 2H), 8.02-7.72 (m, 16H), 7.42-7.40 (m, 4H) , 7.29 (t, 2 H)

MS/FAB: 692(M+)
MS / FAB: 692 (M + )

[합성예 30] 화합물 [30]의 합성[Synthesis Example 30] Synthesis of compound [30]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.85~7.65(m, 12H), 7.56~7.54(m, 4H), 7.29~7.22(m, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.85 ~ 7.65 (m, 12H), 7.56 ~ 7.54 (m, 4H) , 7.29-7.22 (m, 6H)

MS/FAB: 660(M+)
MS / FAB: 660 (M + )

[합성예 31] 화합물 [31]의 합성[Synthesis Example 31] Synthesis of Compound [31]

1H NMR (300 MHz, CDCl3): δ 8.89~8.83(m, 6H), 8.24~8.21(m, 4H), 8.02~8.00(m, 6H), 7.81~7.72(m, 10H), 7.61(s, 4H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.89-8.83 (m, 6H), 8.24-8.21 (m, 4H), 8.02-8.00 (m, 6H), 7.81-7.72 (m, 10H), 7.61 ( s, 4H), 7.29 (t, 2H)

MS/FAB: 680(M+)
MS / FAB: 680 (M + )

[합성예 32] 화합물 [32]의 합성[Synthesis Example 32] Synthesis of compound [32]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 6H), 8.21(s, 2H), 8.02(d, 6H), 7.83~7.72(m, 16H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 6H), 8.21 (s, 2H), 8.02 (d, 6H), 7.83-7.72 (m, 16H), 7.29 (t, 2H)

MS/FAB: 680(M+)
MS / FAB: 680 (M + )

[합성예 33] 화합물 [33]의 합성[Synthesis Example 33] Synthesis of compound [33]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.17~8.03(m, 8H), 7.90~7.81(m, 10H), 7.70(d, 8H), 7.38(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.17 to 8.03 (m, 8H), 7.90 to 7.81 (m, 10H), 7.70 (d, 8H) , 7.38 (t, 2 H)

MS/FAB: 728(M+)MS / FAB: 728 (M + )

[합성예 34] 화합물 [34]의 합성[Synthesis Example 34] Synthesis of compound [34]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.11(d, 2H). 7.96~7.81(m, 14H), 7.60(d, 2H), 7.38~7.36(m, 14H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.11 (d, 2H). 7.96-7.81 (m, 14H), 7.60 (d, 2H), 7.38-7.36 (m, 14H)

MS/FAB: 828(M+)
MS / FAB: 828 (M + )

[합성예 35] 화합물 [35]의 합성[Synthesis Example 35] Synthesis of compound [35]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.41(d, 4H), 8.30(s, 2H), 8.11~8.09(m, 6H), 7.95~7.78(m, 14H), 7.57(t, 2H), 7.38(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.41 (d, 4H), 8.30 (s, 2H), 8.11 to 8.09 (m, 6H), 7.95 to 7.78 (m, 14H) , 7.57 (t, 2 H), 7.38 (d, 2 H)

MS/FAB: 728(M+)
MS / FAB: 728 (M + )

[합성예 36] 화합물 [36]의 합성[Synthesis Example 36] Synthesis of compound [36]

1H NMR (300 MHz, CDCl3): δ 9.14(s, 2H), 8.92(d, 6H), 8.30(s, 2H), 8.17~8.03(m, 10H), 7.90~7.81(m, 14H), 7.38(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.14 (s, 2H), 8.92 (d, 6H), 8.30 (s, 2H), 8.17 to 8.03 (m, 10H), 7.90 to 7.81 (m, 14H) , 7.38 (t, 2 H)

MS/FAB: 780(M+)
MS / FAB: 780 (M + )

[합성예 37] 화합물 [37]의 합성[Synthesis Example 37] Synthesis of compound [37]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.10(d, 2H), 7.98~7.74(m, 16H), 7.62~7.54(m, 4H), 7.38~7.15(m, 18H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.10 (d, 2H), 7.98-7.74 (m, 16H), 7.62-7.54 (m, 4H) , 7.38-7.15 (m, 18H)

MS/FAB: 957(M+)
MS / FAB: 957 (M + )

[합성예 38] 화합물 [38]의 합성[Synthesis Example 38] Synthesis of compound [38]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.11(d, 2H), 7.92~7.76(m, 12H), 7.63(d, 2H), 7.54(d, 2H), 7.32~7.25(m, 18H), 7.10(d, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.11 (d, 2H), 7.92-7.72 (m, 12H), 7.63 (d, 2H), 7.54 (d, 2H), 7.32-7.25 (m, 18H), 7.10 (d, 8H)

MS/FAB: 961(M+)
MS / FAB: 961 (M + )

[합성예 39] 화합물 [39]의 합성[Synthesis Example 39] Synthesis of compound [39]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.54(d, 2H), 8.41(d, 2H), 8.30(s, 2H), 8.11~8.03(m, 6H), 7.90~7.81(m, 6H), 7.60~7.54(m, 6H), 7.38(t, 2H), 7.24(d, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.54 (d, 2H), 8.41 (d, 2H), 8.30 (s, 2H), 8.11 to 8.03 (m, 6H), 7.90 ~ 7.81 (m, 6H), 7.60-7.54 (m, 6H), 7.38 (t, 2H), 7.24 (d, 8H)

MS/FAB: 732(M+)
MS / FAB: 732 (M + )

[합성예 40] 화합물 [40]의 합성[Synthesis Example 40] Synthesis of compound [40]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.54(d, 2H), 8.41(d, 2H), 8.30(s, 2H). 8.11~8.03(m, 6H), 7.90~7.81(m, 6H), 7.69(s, 2H), 7.60~7.38(m, 14H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.54 (d, 2H), 8.41 (d, 2H), 8.30 (s, 2H). 8.11-8.03 (m, 6H), 7.90-7.81 (m, 6H), 7.69 (s, 2H), 7.60-7.38 (m, 14H)

MS/FAB: 732(M+)
MS / FAB: 732 (M + )

[합성예 41] 화합물 [41]의 합성[Synthesis Example 41] Synthesis of compound [41]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.54(d, 4H), 8.30(s, 2H), 8.11(d, 2H), 8.00(d, 4H), 7.90~7.78(m, 10H), 7.54~7.38(m, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.54 (d, 4H), 8.30 (s, 2H), 8.11 (d, 2H), 8.00 (d, 4H), 7.90 ~ 7.78 (m, 10H), 7.54-7.38 (m, 12H)

, MS/FAB: 732(M+)
, MS / FAB: 732 (M + )

[합성예 42] 화합물 [42]의 합성[Synthesis Example 42] Synthesis of compound [42]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.11(d, 2H), 7.99~7.81(m, 12H), 7.72(d, 2H), 7.58~7.57(m, 6H), 7.38(t, 2H), 7.24(d, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.11 (d, 2H), 7.99-7.81 (m, 12H), 7.72 (d, 2H), 7.58 ~ 7.57 (m, 6H), 7.38 (t, 2H), 7.24 (d, 8H)

MS/FAB: 732(M+)
MS / FAB: 732 (M + )

[합성예 43] 화합물 [43]의 합성[Synthesis Example 43] Synthesis of compound [43]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.10(d, 2H), 7.99~7.69(m, 16H), 7.58~7.38(m, 14H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.10 (d, 2H), 7.99 to 7.69 (m, 16H), 7.58 to 7.38 (m, 14H)

MS/FAB: 732(M+)
MS / FAB: 732 (M + )

[합성예 44] 화합물 [44]의 합성[Synthesis Example 44] Synthesis of compound [44]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 6H), 8.30(s, 2H), 8.11(d, 6H), 7.92~7.81(m, 16H), 7.38(t, 2H), 7.24(d, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 6H), 8.30 (s, 2H), 8.11 (d, 6H), 7.92-7.81 (m, 16H), 7.38 (t, 2H), 7.24 (d, 8H)

MS/FAB: 833(M+)
MS / FAB: 833 (M + )

[합성예 45] 화합물 [45]의 합성[Synthesis Example 45] Synthesis of compound [45]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.11(d, 2H), 7.92~7.76(m, 12H), 7.62(d, 2H), 7.54(d, 2H), 7.38~7.37(m, 4H), 7.27~7.24(d, 10H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.11 (d, 2H), 7.92-7.72 (m, 12H), 7.62 (d, 2H), 7.54 (d, 2H), 7.38-7.37 (m, 4H), 7.27-7.74 (d, 10H), 1.67 (s, 12H)

MS/FAB: 865(M+)
MS / FAB: 865 (M + )

[합성예 46] 화합물 [46]의 합성[Synthesis Example 46] Synthesis of compound [46]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.17~8.03(m, 8H), 7.90~7.81(m, 10H), 7.70(d, 8H), 7.38(t, 2H), 7.24(d, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.17 to 8.03 (m, 8H), 7.90 to 7.81 (m, 10H), 7.70 (d, 8H) , 7.38 (t, 2 H), 7.24 (d, 8 H)

MS/FAB: 881(M+)
MS / FAB: 881 (M + )

[합성예 47] 화합물 [47]의 합성[Synthesis Example 47] Synthesis of compound [47]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.11(d, 2H), 7.90~7.81(m, 6H), 7.51~7.50(m, 8H), 7.40~7.38(m, 4H), 7.24(d, 16H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.11 (d, 2H), 7.90-7.81 (m, 6H), 7.51-7.50 (m, 8H) , 7.40 to 7.38 (m, 4H), 7.24 (d, 16H)

MS/FAB: 784(M+)
MS / FAB: 784 (M + )

[합성예 48] 화합물 [48]의 합성[Synthesis Example 48] Synthesis of compound [48]

1H NMR (300 MHz, CDCl3): δ 8.92(d, 2H), 8.30(s, 2H), 8.11(d, 2H), 7.90~7.81(m, 6H), 7.69(t, 2H), 7.56~7.40(m, 18H), 7.24(d, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (d, 2H), 8.30 (s, 2H), 8.11 (d, 2H), 7.90-7.81 (m, 6H), 7.69 (t, 2H), 7.56 ~ 7.40 (m, 18H), 7.24 (d, 8H)

MS/FAB: 784(M+)
MS / FAB: 784 (M + )

[합성예 49] 화합물 [49]의 합성[Synthesis Example 49] Synthesis of compound [49]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 10H), 7.42~7.29(m, 16H), 7.15(s, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 10H), 7.42-7.29 (m, 16H) , 7.15 (s, 8H)

MS/FAB: 784(M+)MS / FAB: 784 (M + )

[합성예 50] 화합물 [50]의 합성[Synthesis Example 50] Synthesis of compound [50]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.05~8.02(m, 4H), 7.81~7.67(m, 12H), 7.59(t, 4H), 7.45(d, 2H), 7.29~7.28(m, 4H), 7.18(t, 2H), 1.62(s, 24H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.05 to 8.02 (m, 4H), 7.81 to 7.57 (m, 12H), 7.59 (t, 4H) , 7.45 (d, 2H), 7.29-7.28 (m, 4H), 7.18 (t, 2H), 1.62 (s, 24H)

MS/FAB: 945(M+)
MS / FAB: 945 (M + )

[합성예 51] 화합물 [51]의 합성[Synthesis Example 51] Synthesis of compound [51]

1H NMR (300 MHz, CDCl3): δ 9.05(s, 2H), 8.83(d, 6H), 8.21(d, 2H), 8.12(d, 6H), 7.81~7.72(m, 14H), 7.61(d, 4H), 7.29(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.05 (s, 2H), 8.83 (d, 6H), 8.21 (d, 2H), 8.12 (d, 6H), 7.81 ~ 7.72 (m, 14H), 7.61 (d, 4H), 7.29 (d, 2H)

MS/FAB: 780(M+)
MS / FAB: 780 (M + )

[합성예 52] 화합물 [52]의 합성[Synthesis Example 52] Synthesis of compound [52]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.45(d, 6H), 8.32(d, 2H), 8.21(s, 2H), 8.02~7.91(m, 10H), 7.81~7.72(m, 6H), 7.51~7.45(m, 10H), 7.29(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.45 (d, 6H), 8.32 (d, 2H), 8.21 (s, 2H), 8.02 to 7.91 (m, 10H), 7.81 ~ 7.72 (m, 6H), 7.51-7.45 (m, 10H), 7.29 (d, 2H)

MS/FAB: 833(M+)
MS / FAB: 833 (M + )

[합성예 53] 화합물 [53]의 합성[Synthesis Example 53] Synthesis of compound [53]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.45(d, 4H), 8.21(s, 2H), 8.02(d, 2H), 7.91~7.72(m, 16H), 7.63(d, 2H), 7.49~7.45(m, 10H), 7.29(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.45 (d, 4H), 8.21 (s, 2H), 8.02 (d, 2H), 7.91-7.72 (m, 16H), 7.63 (d, 2H), 7.49-7.45 (m, 10H), 7.29 (d, 2H)

MS/FAB: 833(M+)
MS / FAB: 833 (M + )

[합성예 54] 화합물 [54]의 합성[Synthesis Example 54] Synthesis of compound [54]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.83~7.67(m, 14H), 7.53(d, 4H), 7.42~7.29(m, 12H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.83 ~ 7.67 (m, 14H), 7.53 (d, 4H), 7.42 ~ 7.29 (m, 12H), 1.62 (s, 12H)

MS/FAB: 865(M+)
MS / FAB: 865 (M + )

[합성예 55] 화합물 [55]의 합성[Synthesis Example 55] Synthesis of compound [55]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21~8.18(m, 4H), 8.05~8.02(m, 4H), 7.91~7.72(m, 12H), 7.59(d, 2H), 7.48~7.42(m, 6H), 7.29(d, 2H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21-8.18 (m, 4H), 8.05-8.02 (m, 4H), 7.91-7.72 (m, 12H), 7.59 (d, 2H), 7.48-7.42 (m, 6H), 7.29 (d, 2H), 1.68 (s, 12H)

MS/FAB: 813(M+)
MS / FAB: 813 (M + )

[합성예 56] 화합물 [56]의 합성[Synthesis Example 56] Synthesis of compound [56]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.08~7.72(m, 20H), 7.59(d, 2H), 7.44~7.42(m, 4H), 7.29(d, 2H), 1.75(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.08 to 7.72 (m, 20H), 7.59 (d, 2H), 7.44 to 7.42 (m, 4H) , 7.29 (d, 2H), 1.75 (s, 12H)

MS/FAB: 813(M+)
MS / FAB: 813 (M + )

[합성예 57] 화합물 [57]의 합성[Synthesis Example 57] Synthesis of compound [57]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(d, 2H), 2.77(m, 1H), 2.54(s, 3H), 1.23(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (d, 2H), 2.77 (m, 1 H), 2.54 (s, 3 H), 1.23 (s, 6 H)

, MS/FAB: 384(M+)
, MS / FAB: 384 (M + )

[합성예 58] 화합물 [58]의 합성[Synthesis Example 58] Synthesis of compound [58]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(d, 2H), 2.54(s, 3H), 1.38(s, 9H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (d, 2H), 2.54 (s, 3H), 1.38 (s, 9H)

MS/FAB: 398(M+)
MS / FAB: 398 (M + )

[합성예 59] 화합물 [59]의 합성[Synthesis Example 59] Synthesis of compound [59]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.42~7.29(m, 7H), 2.54(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.42-7.29 (m, 7H) , 2.54 (s, 3H)

MS/FAB: 418(M+)
MS / FAB: 418 (M + )

[합성예 60] 화합물 [60]의 합성[Synthesis Example 60] Synthesis of Compound [60]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29~7.19(m, 6H), 2.54(s, 3H), 2.24(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29-7.19 (m, 6H) , 2.54 (s, 3H), 2.24 (s, 3H)

MS/FAB: 432(M+)
MS / FAB: 432 (M + )

[합성예 61] 화합물 [61]의 합성[Synthesis Example 61] Synthesis of compound [61]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.50(d, 2H), 7.29~7.21(m, 3H), 2.54(s, 3H), 2.24(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.50 (d, 2H), 7.29 ~ 7.21 (m, 3H), 2.54 (s, 3H), 2.24 (s, 6H)

MS/FAB: 446(M+)
MS / FAB: 446 (M + )

[합성예 62] 화합물 [62]의 합성[Synthesis Example 62] Synthesis of compound [62]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29~7.27(m, 6H), 2.54(s, 3H), 1.25(s, 9H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29-7.27 (m, 6H) , 2.54 (s, 3H), 1.25 (s, 9H)

MS/FAB: 474(M+)
MS / FAB: 474 (M + )

[합성예 63] 화합물 [63]의 합성[Synthesis Example 63] Synthesis of compound [63]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.67(m, 8H), 7.36~7.29(m, 4H), 2.54(s, 3H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81 ~ 7.67 (m, 8H), 7.36 ~ 7.29 (m, 4H) , 2.54 (s, 3H), 0.15 (s, 9H)

MS/FAB: 490(M+)
MS / FAB: 490 (M + )

[합성예 64] 화합물 [64]의 합성[Synthesis Example 64] Synthesis of compound [64]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.58(d, 2H), 7.29~7.28(m, 4H), 2.54(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.58 (d, 2H), 7.29 ~ 7.28 (m, 4H), 2.54 (s, 3H)

MS/FAB: 486(M+)
MS / FAB: 486 (M + )

[합성예 65] 화합물 [65]의 합성[Synthesis Example 65] Synthesis of compound [65]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 10H), 7.29(t, 2H), 2.54(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 10H), 7.29 (t, 2H), 2.54 (s, 3H)

MS/FAB: 443(M+)MS / FAB: 443 (M + )

[합성예 66] 화합물 [66]의 합성[Synthesis Example 66] Synthesis of compound [66]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.82~7.72(m, 10H), 7.49~7.48(m, 3H), 7.29(t, 2H), 2.54(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.82-7.72 (m, 10H), 7.49-7.48 (m, 3H) , 7.29 (t, 2H), 2.54 (s, 3H)

MS/FAB: 468(M+)
MS / FAB: 468 (M + )

[합성예 67] 화합물 [67]의 합성[Synthesis Example 67] Synthesis of compound [67]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.45(d, 1H), 8.32(d, 1H), 8.21(s, 2H), 8.02~7.94(m, 4H), 7.81~7.72(m, 6H), 7.51~7.45(m, 3H), 7.29(t, 2H), 2.54(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.21 (s, 2H), 8.02 to 7.94 (m, 4H), 7.81 ~ 7.72 (m, 6H), 7.51-7.45 (m, 3H), 7.29 (t, 2H), 2.54 (s, 3H)

MS/FAB: 468(M+)
MS / FAB: 468 (M + )

[합성예 68] 화합물 [68]의 합성[Synthesis Example 68] Synthesis of compound [68]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.42~7.29(m, 7H), 7.15(d, 4H), 2.54(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.42-7.29 (m, 7H) , 7.15 (d, 4H), 2.54 (s, 3H)

MS/FAB: 494(M+)
MS / FAB: 494 (M + )

[합성예 69] 화합물 [69]의 합성[Synthesis Example 69] Synthesis of compound [69]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.60(s, 1H), 7.47~7.29(m, 10H), 2.54(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.60 (s, 1H), 7.47 ~ 7.29 (m, 10H), 2.54 (s, 3H)

MS/FAB: 494(M+)
MS / FAB: 494 (M + )

[합성예 70] 화합물 [70]의 합성[Synthesis Example 70] Synthesis of compound [70]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 10H), 7.41~7.29(m, 7H), 2.54(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 10H), 7.41-7.29 (m, 7H) , 2.54 (s, 3H)

MS/FAB: 494(M+)
MS / FAB: 494 (M + )

[합성예 71] 화합물 [71]의 합성[Synthesis Example 71] Synthesis of compound [71]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.45(d, 1H), 8.32(d, 1H), 8.21(s, 2H), 8.02~7.94(m, 4H), 7.81~7.72(m, 6H), 7.51~7.29(m, 10H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.21 (s, 2H), 8.02 to 7.94 (m, 4H), 7.81 ~ 7.72 (m, 6H), 7.51-7.29 (m, 10H)

MS/FAB: 530(M+)
MS / FAB: 530 (M + )

[합성예 72] 화합물 [72]의 합성[Synthesis Example 72] Synthesis of compound [72]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.82~7.63(m, 10H), 7.49~7.29(m, 10H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.82-7.63 (m, 10H), 7.49-7.29 (m, 10H)

MS/FAB: 530(M+)
MS / FAB: 530 (M + )

[합성예 73] 화합물 [73]의 합성[Synthesis Example 73] Synthesis of compound [73]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.42~7.29(m, 12H), 7.15(d, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.42-7.29 (m, 12H) , 7.15 (d, 4 H)

MS/FAB: 556(M+)
MS / FAB: 556 (M + )

[합성예 74] 화합물 [74]의 합성[Synthesis Example 74] Synthesis of compound [74]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.60(s, 1H), 7.47~7.29(m, 15H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.60 (s, 1H), 7.47 ~ 7.29 (m, 15H)

MS/FAB: 556(M+)
MS / FAB: 556 (M + )

[합성예 75] 화합물 [75]의 합성[Synthesis Example 75] Synthesis of Compound [75]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.69(m, 10H), 7.42~7.29(m, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.69 (m, 10H), 7.42-7.29 (m, 12H)

MS/FAB: 556(M+)
MS / FAB: 556 (M + )

[합성예 76] 화합물 [76]의 합성[Synthesis Example 76] Synthesis of compound [76]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.83~7.67(m, 9H), 7.53(d, 1H), 7.45~7.28(m, 9H), 7.18(t, 1H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.83 ~ 7.67 (m, 9H), 7.53 (d, 1H), 7.45 ~ 7.28 (m, 9H), 7.18 (t, 1H), 1.62 (s, 6H)

MS/FAB: 596(M+)
MS / FAB: 596 (M + )

[합성예 77] 화합물 [77]의 합성[Synthesis Example 77] Synthesis of compound [77]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.67(m, 8H), 7.42~7.29(m, 9H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.67 (m, 8H), 7.42-7.29 (m, 9H) , 0.15 (s, 9H)

MS/FAB: 552(M+)
MS / FAB: 552 (M + )

[합성예 78] 화합물 [78]의 합성[Synthesis Example 78] Synthesis of compound [78]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 8H), 7.45~7.27(m, 24H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 8H), 7.45-7.27 (m, 24H)

MS/FAB: 738(M+)
MS / FAB: 738 (M + )

[합성예 79] 화합물 [79]의 합성[Synthesis Example 79] Synthesis of compound [79]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.56(s, 3H), 7.42~7.29(m, 17H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.56 (s, 3H), 7.42 ~ 7.29 (m, 17H)

MS/FAB: 632(M+)
MS / FAB: 632 (M + )

[합성예 80] 화합물 [80]의 합성[Synthesis Example 80] Synthesis of compound [80]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 4H), 8.21(s, 2H), 8.02(d, 4H), 7.83~7.72(m, 11H), 7.42~7.29(m, 7H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 4H), 8.21 (s, 2H), 8.02 (d, 4H), 7.83-7.72 (m, 11H), 7.42-7.29 (m, 7H)

MS/FAB: 580(M+)
MS / FAB: 580 (M + )

[합성예 81] 화합물 [81]의 합성[Synthesis Example 81] Synthesis of compound [81]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.02(m, 2H), 7.85~7.72(m, 9H), 7.51(m, 1H), 7.42~7.25(m, 10H), 0.56(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.02 (m, 2H), 7.85-7.72 (m, 9H), 7.51 (m, 1H), 7.42 ~ 7.25 (m, 10H), 0.56 (s, 6H)

MS/FAB: 612(M+)MS / FAB: 612 (M + )

[합성예 82] 화합물 [82]의 합성[Synthesis Example 82] Synthesis of compound [82]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.35(d, 1H), 8.21(s, 2H), 8.02~7.72(m, 12H), 7.42~7.29(m, 9H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.35 (d, 1H), 8.21 (s, 2H), 8.02-7.72 (m, 12H), 7.42-7.29 (m, 9H)

MS/FAB: 586(M+)
MS / FAB: 586 (M + )

[합성예 83] 화합물 [83]의 합성[Synthesis Example 83] Synthesis of compound [83]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.02(m, 2H), 7.85~7.65(m, 9H), 7.56~7.54(m, 2H), 7.42~7.22(m, 9H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.02 (m, 2H), 7.85 ~ 7.65 (m, 9H), 7.56 ~ 7.54 (m, 2H) , 7.42-7.22 (m, 9H)

MS/FAB: 570(M+)
MS / FAB: 570 (M + )

[합성예 84] 화합물 [84]의 합성[Synthetic Example 84] Synthesis of compound [84]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.08~7.94(m, 5H), 7.81~7.72(m, 8H), 7.61(s, 4H), 7.42~7.29(m, 7H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.08 to 7.94 (m, 5H), 7.81 to 7.72 (m, 8H), 7.61 (s, 4H) , 7.42-7.29 (m, 7H)

MS/FAB: 604(M+)
MS / FAB: 604 (M + )

[합성예 85] 화합물 [85]의 합성[Synthesis Example 85] Synthesis of compound [85]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 10H), 7.51(d, 1H), 7.42~7.29(m, 13H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 10H), 7.51 (d, 1H), 7.42 ~ 7.29 (m, 13H)

MS/FAB: 654(M+)
MS / FAB: 654 (M + )

[합성예 86] 화합물 [86]의 합성[Synthesis Example 86] Synthesis of compound [86]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.32(d, 2H), 8.21(s, 2H), 8.02~8.00(m, 4H), 7.86~7.69(m, 10H), 7.48~7.29(m, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.32 (d, 2H), 8.21 (s, 2H), 8.02-8.00 (m, 4H), 7.86-7.69 (m, 10H) , 7.48-7.29 (m, 8H)

MS/FAB: 604(M+)
MS / FAB: 604 (M + )

[합성예 87] 화합물 [87]의 합성 [Synthesis Example 87] Synthesis of compound [87]

1H NMR (300 MHz, CDCl3): δ 9.05(s, 1H), 8.83(d, 4H), 8.21(s, 2H), 8.02~7.94(m, 6H), 7.81~7.72(m, 10H), 7.42~7.29(m, 7H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.05 (s, 1H), 8.83 (d, 4H), 8.21 (s, 2H), 8.02 ~ 7.94 (m, 6H), 7.81 ~ 7.72 (m, 10H) , 7.42-7.29 (m, 7H)

MS/FAB: 630(M+)
MS / FAB: 630 (M + )

[합성예 88] 화합물 [88]의 합성[Synthesis Example 88] Synthesis of compound [88]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.65(m, 15H). 7.53~7.45(m, 5H), 7.29~7.09(m, 10H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.75 (m, 15H). 7.53-7.45 (m, 5H), 7.29-7.09 (m, 10H)

MS/FAB: 768(M+)
MS / FAB: 768 (M + )

[합성예 89] 화합물 [89]의 합성[Synthesis Example 89] Synthesis of compound [89]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.72(m, 13H). 7.53~7.45(m, 5H), 7.29~7.16(m, 10H), 7.01(m 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.72 (m, 13H). 7.53-7.45 (m, 5H), 7.29-7.16 (m, 10H), 7.01 (m 4H)

, MS/FAB: 770(M+)
, MS / FAB: 770 (M + )

[합성예 90] 화합물 [90]의 합성[Synthesis Example 90] Synthesis of Compound [90]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.45(m, 1H), 8.32(m, 1H), 8.21(s, 2H), 7.98~7.72(m, 14H). 7.51~7.45(m, 6H), 7.29(m, 2H), 7.15(s 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.45 (m, 1H), 8.32 (m, 1H), 8.21 (s, 2H), 7.98-7.72 (m, 14H). 7.51 to 7.45 (m, 6H), 7.29 (m, 2H), 7.15 (s 4H)

MS/FAB: 656(M+)
MS / FAB: 656 (M + )

[합성예 91] 화합물 [91]의 합성 [Synthesis 91] Synthesis of compound [91]

1H NMR (300 MHz, CDCl3): δ δ 8.83(m, 2H), 8.45(m, 1H), 8.32(m, 1H), 8.21(s, 2H), 7.98~7.60(m, 15H). 7.51~7.29(m, 11H) 1 H NMR (300 MHz, CDCl 3 ): δ δ 8.83 (m, 2H), 8.45 (m, 1H), 8.32 (m, 1H), 8.21 (s, 2H), 7.98-7.60 (m, 15H). 7.51 ~ 7.29 (m, 11H)

MS/FAB: 656(M+)
MS / FAB: 656 (M + )

[합성예 92] 화합물 [92]의 합성 [Synthesis Example 92] Synthesis of compound [92]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.45(m, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.91~7.69(m, 14H). 7.49~7.29(m, 10H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.45 (m, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.91-7.69 (m, 14H). 7.49-7.29 (m, 10H)

MS/FAB: 656(M+)
MS / FAB: 656 (M + )

[합성예 93] 화합물 [93]의 합성[Synthesis Example 93] Synthesis of compound [93]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.63(m, 14H). 7.49~7.48(m, 6H), 7.29(m,2H), 7.15(s, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.63 (m, 14H). 7.49 to 7.48 (m, 6H), 7.29 (m, 2H), 7.15 (s, 4H)

MS/FAB: 656(M+)
MS / FAB: 656 (M + )

[합성예 94] 화합물 [94]의 합성[Synthesis Example 94] Synthesis of compound [94]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.63(m, 15H). 7.49~7.47(m, 7H), 7.38(m, 2H), 7.29(m,2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.63 (m, 15H). 7.49-7.47 (m, 7H), 7.38 (m, 2H), 7.29 (m, 2H)

MS/FAB: 656(M+)
MS / FAB: 656 (M + )

[합성예 95] 화합물 [95]의 합성[Synthesis Example 95] Synthesis of compound [95]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 4H), 8.21(s, 2H), 8.02(d, 4H), 7.90~7.63(m, 15H). 7.49~7.48(m, 3H), 7.29(m, 2H), 7.15s(s, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 4H), 8.21 (s, 2H), 8.02 (d, 4H), 7.90-7.63 (m, 15H). 7.49 to 7.48 (m, 3H), 7.29 (m, 2H), 7.15 s (s, 4H)

MS/FAB: 706(M+)
MS / FAB: 706 (M + )

[합성예 96] 화합물 [96]의 합성[Synthesis Example 96] Synthesis of compound [96]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.67(m, 13H), 7.53~7.45(m, 5H), 7.29~7.28(m, 3H), 7.15s(s, 5H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.67 (m, 13H), 7.53-7.45 (m, 5H) , 7.29-7.28 (m, 3H), 7.15s (s, 5H), 1.62 (s, 6H)

MS/FAB: 722(M+)
MS / FAB: 722 (M + )

[합성예 97] 화합물 [97]의 합성[Synthesis Example 97] Synthesis of compound [97]

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.41(s, 2H), 8.28~7.81(m, 21), 7.69~7.68(m, 3H), 7.49(s, 2H), 7.35(s, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.41 (s, 2H), 8.28 ~ 7.81 (m, 21), 7.69 ~ 7.68 (m, 3H), 7.49 (s, 2H) , 7.35 (s, 4H)

MS/FAB: 730(M+)
MS / FAB: 730 (M + )

[합성예 98] 화합물 [98]의 합성[Synthesis Example 98] Synthesis of compound [98]

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.10~7.92(m, 9H), 7.83(s, 1H), 7.69~7.61(m, 7H), 7.51~7.49(m, 3H), 7.35(s, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.10 ~ 7.92 (m, 9H), 7.83 (s, 1H), 7.69 ~ 7.61 (m, 7H), 7.51-7.49 (m, 3H), 7.35 (s, 8H)

MS/FAB: 682(M+)
MS / FAB: 682 (M + )

[합성예 99] 화합물 [99]의 합성[Synthesis Example 99] Synthesis of compound [99]

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.10~7.80(m, 11H), 7.69~7.49(m, 13H), 7.35(s, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.10 ~ 7.80 (m, 11H), 7.69 ~ 7.49 (m, 13H) , 7.35 (s, 4H)

MS/FAB: 682(M+)
MS / FAB: 682 (M + )

[합성예 100] 화합물 [100]의 합성[Synthesis Example 100] Synthesis of Compound [100]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.10~7.83(m, 12H), 7.69~7.49(m, 12H), 7.35(s, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.10-7.83 (m, 12H), 7.69-7.49 (m, 12H) , 7.35 (s, 4H)

MS/FAB: 682(M+)
MS / FAB: 682 (M + )

[합성예 101] 화합물 [101]의 합성[Synthesis Example 101] Synthesis of compound [101]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.25~8.22(m, 3H), 8.10(t, 2H), 8.02~7.79(m, 13H), 7.69~7.65(m, 4H), 7.49~7.48(m, 3H), 7.38(t, 1H), 1.82(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.25 to 8.22 (m, 3H), 8.10 (t, 2H), 8.02 to 7.79 (m, 13H) , 7.69-7.75 (m, 4H), 7.49-7.48 (m, 3H), 7.38 (t, 1H), 1.82 (s, 12H)

MS/FAB: 762(M+)
MS / FAB: 762 (M + )

[합성예 102] 화합물 [102]의 합성[Synthesis Example 102] Synthesis of compound [102]

1H NMR (300 MHz, CDCl3): δ 9.25(s, 1H), 9.03(s, 4H), 8.41(s, 2H), 8.22(s, 4H), 8.10~7.81(m, 16H), 7.69~7.68(m, 3H), 7.49(s, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.25 (s, 1H), 9.03 (s, 4H), 8.41 (s, 2H), 8.22 (s, 4H), 8.10 ~ 7.81 (m, 16H), 7.69 ~ 7.68 (m, 3H), 7.49 (s, 2H)

MS/FAB: 680(M+)
MS / FAB: 680 (M + )

[합성예 103] 화합물 [103]의 합성Synthesis Example 103 Synthesis of Compound [103]

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.65(s, 3H), 8.52(s, 1H), 8.41(s, 2H), 8.22~7.83(m, 16H), 7.71~7.65(m, 8H), 7.49(s, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.65 (s, 3H), 8.52 (s, 1H), 8.41 (s, 2H), 8.22-7.83 (m, 16H), 7.71 ~ 7.65 (m, 8H), 7.49 (s, 2H)

MS/FAB: 706(M+)
MS / FAB: 706 (M + )

[합성예 104] 화합물 [104]의 합성Synthesis Example 104 Synthesis of Compound

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.65(s, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.11~7.83(m, 16H), 7.69~7.65(m, 8H), 7.49(s, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.65 (s, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.11-7.83 (m, 16H), 7.69 ~ 7.65 (m, 8H), 7.49 (s, 2H)

MS/FAB: 706(M+)
MS / FAB: 706 (M + )

[합성예 105] 화합물 [105]의 합성Synthesis Example 105 Synthesis of Compound [105]

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.10~7.83(m, 14H), 7.69~7.49(m, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.10-7.83 (m, 14H), 7.69-7.49 (m, 12H)

MS/FAB: 656(M+)
MS / FAB: 656 (M + )

[합성예 106] 화합물 [106]의 합성Synthesis Example 106 Synthesis of Compound [106]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.10~7.83(m, 14H), 7.73~7.49(m, 12H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.10-7.83 (m, 14H), 7.73-7.49 (m, 12H) , 1.82 (s, 6H)

MS/FAB: 722(M+)
MS / FAB: 722 (M + )

[합성예 107] 화합물 [107]의 합성Synthesis Example 107 Synthesis of Compound [107]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.25~7.79(m, 19H), 7.69~7.62(m, 5H), 7.49(s, 2H), 1.95(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.25 ~ 7.79 (m, 19H), 7.69 ~ 7.62 (m, 5H), 7.49 (s, 2H) , 1.95 (s, 6H)

MS/FAB: 696(M+)
MS / FAB: 696 (M + )

[합성예 108] 화합물 [108]의 합성Synthesis Example 108 Synthesis of Compound [108]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41~8.38(m, 3H), 8.25~8.22(m, 3H), 8.11~7.92(m, 12H), 7.83~7.79(m, 2H), 7.69~7.62(m, 6H), 7.49(d, 2H), 1.88(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 to 8.38 (m, 3H), 8.25 to 8.22 (m, 3H), 8.11 to 7.82 (m, 12H), 7.83 to 7.79 ( m, 2H), 7.69-7.82 (m, 6H), 7.49 (d, 2H), 1.88 (s, 6H)

MS/FAB: 696(M+)
MS / FAB: 696 (M + )

[합성예 109] 화합물 [109]의 합성Synthesis Example 109 Synthesis of Compound [109]

1H NMR (300 MHz, CDCl3): δ 9.03(d, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.10~7.87(m, 16H), 7.69~7.45(m, 14H), 7.29~7.26(m, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (d, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.10-7.87 (m, 16H), 7.69-7.45 (m, 14H) , 7.29-7.26 (m, 4H)

MS/FAB: 845(M+)
MS / FAB: 845 (M + )

[합성예 110] 화합물 [110]의 합성Synthesis Example 110 Synthesis of Compound [110]

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.60(s, 1H), 8.41(s, 2H), 8.22(s, 2H), 8.10~7.83(m, 10H), 7.69~7.61(m, 4H), 7.49(s, 2H), 7.36(s, 1H), 7.10(t, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.60 (s, 1H), 8.41 (s, 2H), 8.22 (s, 2H), 8.10-7.83 (m, 10H), 7.69 ~ 7.61 (m, 4H), 7.49 (s, 2H), 7.36 (s, 1H), 7.10 (t, 1H)

MS/FAB: 531(M+)
MS / FAB: 531 (M + )

[합성예 111] 화합물 [111]의 합성Synthesis Example 111 Synthesis of Compound [111]

1H NMR (300 MHz, CDCl3): δ 9.34(s, 1H), 9.03(s, 2H), 8.80(s, 1H), 8.52(s, 1H), 8.41(s, 2H), 8.22(s, 2H), 8.10~7.92(m, 10H), 7.69~7.67(m, 4H), 7.49(s, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.34 (s, 1H), 9.03 (s, 2H), 8.80 (s, 1H), 8.52 (s, 1H), 8.41 (s, 2H), 8.22 (s , 2H), 8.10-7.72 (m, 10H), 7.69-7.57 (m, 4H), 7.49 (s, 2H)

MS/FAB: 531(M+)
MS / FAB: 531 (M + )

[합성예 112] 화합물 [112]의 합성Synthesis Example 112 Synthesis of Compound [112]

1H NMR (300 MHz, CDCl3): δ 9.03(s, 2H), 8.85(s, 2H), 8.41(s, 2H), 8.22(s, 2H), 8.10~7.83(m, 12H), 7.69~7.68(m, 3H), 7.49(s, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.03 (s, 2H), 8.85 (s, 2H), 8.41 (s, 2H), 8.22 (s, 2H), 8.10-7.83 (m, 12H), 7.69 ~ 7.68 (m, 3H), 7.49 (s, 2H)

MS/FAB: 531(M+)
MS / FAB: 531 (M + )

[합성예 113] 화합물 [113]의 합성Synthesis Example 113 Synthesis of Compound [113]

1H NMR (300 MHz, CDCl3): δ 9.17(s, 1H), 8.86~8.83(m, 3H), 8.21(s, 2H), 8.02~8.01(m, 3H), 7.91~7.72(m, 10H), 7.49~7.48(m, 3H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.17 (s, 1H), 8.86 to 8.83 (m, 3H), 8.21 (s, 2H), 8.02 to 8.01 (m, 3H), 7.91 to 7.72 (m, 10H), 7.49-7.48 (m, 3H), 7.29 (t, 2H)

MS/FAB: 532(M+)
MS / FAB: 532 (M + )

[합성예 114] 화합물 [114]의 합성Synthesis Example 114 Synthesis of Compound [114]

1H NMR (300 MHz, CDCl3): δ 9.12(s, 1H), 8.90~8.83(m, 4H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.72(m, 10H), 7.49~7.48(m, 3H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.12 (s, 1H), 8.90-8.83 (m, 4H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.72 (m, 10H) , 7.49-7.48 (m, 3H), 7.29 (t, 2H)

MS/FAB: 532(M+)
MS / FAB: 532 (M + )

[합성예 115] 화합물 [115]의 합성Synthesis Example 115 Synthesis of Compound [115]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.69~8.66(m, 3H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.72(m, 10H), 7.49~7.48(m, 3H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.69-8.66 (m, 3H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.72 (m, 10H) , 7.49-7.48 (m, 3H), 7.29 (t, 2H)

MS/FAB: 532(M+)
MS / FAB: 532 (M + )

[합성예 116] 화합물 [116]의 합성Synthesis Example 116 Synthesis of Compound

1H NMR (300 MHz, CDCl3): δ 8.88~8.83(m, 3H), 8.21(s, 2H), 8.02(d, 2H), 7.93~7.72(m, 11H), 7.49~7.48(m, 3H), 7.29(t, 2H), 7.17(t, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.88-8.83 (m, 3H), 8.21 (s, 2H), 8.02 (d, 2H), 7.93-7.72 (m, 11H), 7.49-7.48 (m, 3H), 7.29 (t, 2H), 7.17 (t, 1H)

MS/FAB: 532(M+)
MS / FAB: 532 (M + )

[합성예 117] 화합물 [117]의 합성Synthesis Example 117 Synthesis of Compound [117]

1H NMR (300 MHz, CDCl3): δ 8.83~8.76(m, 4H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.72(m, 10H), 7.49~7.48(m, 3H), 7.29~7.21(m, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83-8.76 (m, 4H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.72 (m, 10H), 7.49-7.48 (m, 3H), 7.29-7.21 (m, 3H)

MS/FAB: 532(M+)
MS / FAB: 532 (M + )

[합성예 118] 화합물 [118]의 합성Synthesis Example 118 Synthesis of Compound [118]

1H NMR (300 MHz, CDCl3): δ 9.36(s, 1H), 9.20(d, 1H), 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.63(m, 11H), 7.49~7.48(m, 3H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.36 (s, 1H), 9.20 (d, 1H), 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90 ~ 7.63 (m, 11H), 7.49-7.48 (m, 3H), 7.29 (t, 2H)

MS/FAB: 532(M+)
MS / FAB: 532 (M + )

[합성예 119] 화합물 [119]의 합성Synthesis Example 119 Synthesis of Compound [119]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.61(s, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.63(m, 10H), 7.49~7.48(m, 3H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.61 (s, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90 ~ 7.63 (m, 10H), 7.49 ~ 7.48 (m, 3H), 7.29 (t, 2H)

MS/FAB: 533(M+)
MS / FAB: 533 (M + )

[합성예 120] 화합물 [120]의 합성[Synthesis Example 120] Synthesis of Compound [120]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.32(d, 1H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.63(m, 11H), 7.53~7.29(m, 8H), 7.00(d, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.32 (d, 1H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90 ~ 7.63 (m, 11H), 7.53 ~ 7.29 (m, 8H), 7.00 (d, 1H)

MS/FAB: 581(M+)
MS / FAB: 581 (M + )

[합성예 121] 화합물 [121]의 합성[Synthesis Example 121] Synthesis of Compound [121]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.73(d, 1H), 8.28~8.21(m, 3H), 8.11(d, 1H), 8.02(d, 2H), 7.90~7.48(m, 16H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.73 (d, 1H), 8.28-8.21 (m, 3H), 8.11 (d, 1H), 8.02 (d, 2H), 7.90 ~ 7.48 (m, 16H), 7.29 (t, 2H)

MS/FAB: 581(M+)
MS / FAB: 581 (M + )

[합성예 122] 화합물 [122]의 합성[Synthesis Example 122] Synthesis of Compound [122]

1H NMR (300 MHz, CDCl3): δ 8.83~8.81(m, 3H), 8.35(d, 1H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.63(12H), 7.49~7.29(m, 7H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83-8.81 (m, 3H), 8.35 (d, 1H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.63 (12H), 7.49 ~ 7.29 (m, 7H)

MS/FAB: 581(M+)
MS / FAB: 581 (M + )

[합성예 123] 화합물 [123]의 합성[Synthesis Example 123] Synthesis of compound [123]

1H NMR (300 MHz, CDCl3): δ 8.83~8.77(m, 3H), 8.33(s, 1H), 8.21(s, 2H), 8.02(d, 2H), 7.90~7.63(m, 12H), 7.49~7.29(m, 7) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83-8.77 (m, 3H), 8.33 (s, 1H), 8.21 (s, 2H), 8.02 (d, 2H), 7.90-7.63 (m, 12H) , 7.49-7.29 (m, 7)

MS/FAB: 581(M+)
MS / FAB: 581 (M + )

[합성예 124] 화합물 [124]의 합성[Synthesis Example 124] Synthesis of Compound [124]

1H NMR (300 MHz, CDCl3): δ 8.83~8.79(m, 3H), 8.21(s, 2H), 8.02~7.63(m, 15H), 7.50~7.48(m, 4H), 7.38(d, 1H), 7.29(t, 2H), 1 H NMR (300 MHz, CDCl 3 ): δ 8.83-8.79 (m, 3H), 8.21 (s, 2H), 8.02-7.63 (m, 15H), 7.50-7.48 (m, 4H), 7.38 (d, 1H), 7.29 (t, 2H),

MS/FAB: 581(M+)
MS / FAB: 581 (M + )

[합성예 125] 화합물 [125]의 합성[Synthesis Example 125] Synthesis of Compound [125]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.73(d, 1H), 8.21(s, 3H), 8.02~7.63(m, 15H), 7.49~7.48(m, 4H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.73 (d, 1H), 8.21 (s, 3H), 8.02-7.63 (m, 15H), 7.49-7.48 (m, 4H) , 7.29 (t, 2 H)

MS/FAB: 581(M+)
MS / FAB: 581 (M + )

[합성예 126] 화합물 [126]의 합성[Synthesis Example 126] Synthesis of Compound [126]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.45(d, 1H), 8.32(d, 1H), 8.21(s, 2H), 8.02~7.63(m, 14H), 7.51~7.45(m, 6H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.45 (d, 1H), 8.32 (d, 1H), 8.21 (s, 2H), 8.02-7.63 (m, 14H), 7.51 ~ 7.45 (m, 6H), 7.29 (t, 2H)

MS/FAB: 580(M+)
MS / FAB: 580 (M + )

[합성예 127] 화합물 [127]의 합성[Synthesis Example 127] Synthesis of Compound [127]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02~7.63(m, 16H), 7.50~7.48(m, 4H), 7.29~7.25(m, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02-7.63 (m, 16H), 7.50-7.48 (m, 4H), 7.29-7.25 (m, 3H)

MS/FAB: 581(M+)
MS / FAB: 581 (M + )

[합성예 128] 화합물 [128]의 합성[Synthesis Example 128] Synthesis of Compound [128]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.47(s, 1H), 8.21(s, 2H), 8.12(s, 1H), 8.02~7.63(m, 15H), 7.50~7.48(m, 4H), 7.29(t, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.47 (s, 1H), 8.21 (s, 2H), 8.12 (s, 1H), 8.02-7.63 (m, 15H), 7.50 ~ 7.48 (m, 4H), 7.29 (t, 2H)

MS/FAB: 581(M+)
MS / FAB: 581 (M + )

[합성예 129] 화합물 [129]의 합성[Synthesis Example 129] Synthesis of Compound [129]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.73(m, 1H), 8.28~8.17(m, 4H), 8.02~7.63(m, 14H), 7.49~7.48(m, 4H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.73 (m, 1H), 8.28 to 8.17 (m, 4H), 8.02 to 7.63 (m, 14H), 7.49 to 7.48 (m, 4H), 7.29 (m, 2H)

MS/FAB: 581.7(M+)
MS / FAB: 581.7 (M + )

[합성예 130] 화합물 [130]의 합성[Synthesis Example 130] Synthesis of Compound [130]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.35(d, 1H), 8.21(s, 2H), 8.02~7.99(m, 3H), 7.90~7.62(m, 12H), 7.49~7.40(m, 4H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.35 (d, 1H), 8.21 (s, 2H), 8.02-7.99 (m, 3H), 7.90-7.82 (m, 12H) , 7.49-7.40 (m, 4H), 7.29 (m, 2H)

MS/FAB: 581.7(M+)
MS / FAB: 581.7 (M + )

[합성예 131] 화합물 [131]의 합성[Synthesis Example 131] Synthesis of Compound [131]

1H NMR (300 MHz, CDCl3): δ 8.83~8.81(m, 3H), 8.35(d, 1H), 8.21(s, 2H), 8.02(m, 2H), 7.90~7.63(m, 13H), 7.49~7.40(m, 4H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83-8.81 (m, 3H), 8.35 (d, 1H), 8.21 (s, 2H), 8.02 (m, 2H), 7.90-7.63 (m, 13H) , 7.49-7.40 (m, 4H), 7.29 (m, 2H)

MS/FAB: 581.7(M+)
MS / FAB: 581.7 (M + )

[합성예 132] 화합물 [132]의 합성[Synthesis Example 132] Synthesis of Compound [132]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.64(s, 2H), 8.21(s, 2H), 8.02(m, 2H), 7.90~7.63(m, 13H), 7.49~7.48(m, 3H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.64 (s, 2H), 8.21 (s, 2H), 8.02 (m, 2H), 7.90-7.63 (m, 13H), 7.49 ~ 7.48 (m, 3H), 7.29 (m, 2H)

MS/FAB: 582.69(M+)
MS / FAB: 582.69 (M + )

[합성예 133] 화합물 [133]의 합성 [Synthesis Example 133] Synthesis of Compound [133]

1H NMR (300 MHz, CDCl3): δ 9.06~9.00(m, 2H), 8.83(m, 2H), 8.40(d, 1H), 8.21(s, 2H), 8.02(m, 2H), 7.90~7.63(m, 12H), 7.49~7.48(m, 3H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.06-9.00 (m, 2H), 8.83 (m, 2H), 8.40 (d, 1H), 8.21 (s, 2H), 8.02 (m, 2H), 7.90 ~ 7.63 (m, 12H), 7.49-7.48 (m, 3H), 7.29 (m, 2H)

MS/FAB: 582.69(M+)
MS / FAB: 582.69 (M + )

[합성예 134] 화합물 [134]의 합성[Synthesis Example 134] Synthesis of compound [134]

1H NMR (300 MHz, CDCl3): δ 9.04(m, 1H), 8.83(m, 2H), 8.69(d, 1H), 8.21(s, 2H), 8.13(d, 1H), 8.02(m, 2H), 7.90~7.63(m, 10H), 7.49~7.48(m, 3H), 7.36~7.29(m, 3H), 7.20(d, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.04 (m, 1H), 8.83 (m, 2H), 8.69 (d, 1H), 8.21 (s, 2H), 8.13 (d, 1H), 8.02 (m , 2H), 7.90-7.63 (m, 10H), 7.49-7.48 (m, 3H), 7.36-7.29 (m, 3H), 7.20 (d, 1H)

MS/FAB: 582.69(M+)
MS / FAB: 582.69 (M + )

[합성예 135] 화합물 [135]의 합성[Synthesis Example 135] Synthesis of compound [135]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.6(s, 1H), 8.21(s, 2H), 8.02(m, 2H), 7.90~7.63(m, 17H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.6 (s, 1H), 8.21 (s, 2H), 8.02 (m, 2H), 7.90 ~ 7.63 (m, 17H), 7.29 (m, 2H)

MS/FAB: 582.69(M+)
MS / FAB: 582.69 (M + )

[합성예 136] 화합물 [136]의 합성[Synthesis Example 136] Synthesis of compound [136]

1H NMR (300 MHz, CDCl3): δ 9.00(d, 1H), 8.83(m, 2H), 8.40(d, 1H), 8.21(s, 2H), 8.12(d, 1H), 8.02(m, 2H), 7.90~7.63(m, 12H), 7.49~7.48(m, 3H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.00 (d, 1H), 8.83 (m, 2H), 8.40 (d, 1H), 8.21 (s, 2H), 8.12 (d, 1H), 8.02 (m , 2H), 7.90-7.63 (m, 12H), 7.49-7.48 (m, 3H), 7.29 (m, 2H)

MS/FAB: 582.69(M+)
MS / FAB: 582.69 (M + )

[합성예 137] 화합물 [137]의 합성[Synthesis Example 137] Synthesis of compound [137]

1H NMR (300 MHz, CDCl3): δ 9.11(d, 1H), 9.00(d, 1H), 8.83(m, 2H), 8.53(d, 1H), 8.40(d, 1H), 8.21(s, 2H), 8.12(d, 2H), 7.90~7.63(m, 11H), 7.49~7.48(m, 3H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.11 (d, 1H), 9.00 (d, 1H), 8.83 (m, 2H), 8.53 (d, 1H), 8.40 (d, 1H), 8.21 (s , 2H), 8.12 (d, 2H), 7.90-7.63 (m, 11H), 7.49-7.48 (m, 3H), 7.29 (m, 2H)

MS/FAB: 582.69(M+)
MS / FAB: 582.69 (M + )

[합성예 138] 화합물 [138]의 합성[Synthesis Example 138] Synthesis of Compound [138]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.64(s, 1H), 8.21~8.19(m, 3H), 8.02(m, 2H), 7.90~7.63(m, 12H), 7.49~7.48(m, 3H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.64 (s, 1H), 8.21-8.19 (m, 3H), 8.02 (m, 2H), 7.90-7.63 (m, 12H) , 7.49-7.48 (m, 3H), 7.29 (m, 2H)

MS/FAB: 582.69(M+)
MS / FAB: 582.69 (M + )

[합성예 139] 화합물 [139]의 합성[Synthesis Example 139] Synthesis of compound [139]

1H NMR (300 MHz, CDCl3): δ 9.29~9.26(d, 2H), 8.83(d, 2H), 8.65(d, 1H), 8.21(s, 2H), 8.02(m, 2H), 7.90~7.63(m, 12H), 7.49~7.48(m, 3H), 7.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.29-9.26 (d, 2H), 8.83 (d, 2H), 8.65 (d, 1H), 8.21 (s, 2H), 8.02 (m, 2H), 7.90 ~ 7.63 (m, 12H), 7.49-7.48 (m, 3H), 7.29 (m, 2H)

MS/FAB: 582.69(M+)
MS / FAB: 582.69 (M + )

[합성예 140] 화합물 [140]의 합성[Synthesis Example 140] Synthesis of Compound [140]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.45(d, 1H), 8.2(s, 2H), 8.02(m, 3H), 7.90~7.63(m, 11H), 7.53~7.40(m, 5H), 7.29~7.15(m, 5H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.45 (d, 1H), 8.2 (s, 2H), 8.02 (m, 3H), 7.90-7.63 (m, 11H), 7.53 ~ 7.40 (m, 5H), 7.29-7.15 (m, 5H)

MS/FAB: 619.75(M+)
MS / FAB: 619.75 (M + )

[합성예 141] 화합물 [141]의 합성[Synthesis Example 141] Synthesis of Compound [141]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.45(d, 1H), 8.2(s, 2H), 8.02(m, 2H), 7.90~7.59(m, 14H), 7.42~7.15(m, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.45 (d, 1H), 8.2 (s, 2H), 8.02 (m, 2H), 7.90 to 7.59 (m, 14H), 7.42 ~ 7.15 (m, 12H)

MS/FAB: 695.85(M+)
MS / FAB: 695.85 (M + )

[합성예 142] 화합물 [142]의 합성[Synthesis Example 142] Synthesis of Compound [142]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.2(s, 2H), 8.02(m, 3H), 7.90~7.59(m, 15H), 7.49~7.31(m, 15H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.2 (s, 2H), 8.02 (m, 3H), 7.90 to 7.59 (m, 15H), 7.49 to 7.31 (m, 15H)

MS/FAB: 771.94(M+)
MS / FAB: 771.94 (M + )

[합성예 143] 화합물 [143]의 합성[Synthesis Example 143] Synthesis of compound [143]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21~8.17(m, 3H), 8.02(m, 3H), 7.90~7.67(m, 12H), 7.49~7.40(m, 4H), 7.29~7.19(m, 4H), 3.72(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 to 8.17 (m, 3H), 8.02 (m, 3H), 7.90 to 7.07 (m, 12H), 7.49 to 7.40 (m, 4H), 7.29-7.19 (m, 4H), 3.72 (s, 3H)

MS/FAB: 633.78(M+)
MS / FAB: 633.78 (M + )

[합성예 144] 화합물 [144]의 합성[Synthesis Example 144] Synthesis of compound [144]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.08~8.02(m, 4H), 7.90~7.67(m, 12H), 7.53~7.29(m, 12H), 7.19(m, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.08 to 8.02 (m, 4H), 7.90 to 7.07 (m, 12H), 7.53 to 7.29 (m, 12H), 7.19 (m, 1H)

MS/FAB: 695.85(M+)
MS / FAB: 695.85 (M + )

[합성예 145] 화합물 [145]의 합성[Synthesis Example 145] Synthesis of Compound [145]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30(s. 2H), 8.17~8.11(m, 4H), 7.90~7.72(m, 11H), 7.61~7.57(m, 5H), 7.41~7.38(m, 4H), 3.81(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30 (s. 2H), 8.17 to 8.11 (m, 4H), 7.90 to 7.72 (m, 11H), 7.61 to 7.57 (m, 5H), 7.41 ~ 7.38 (m, 4H), 3.81 (s, 3H)

MS/FAB: 633.78(M+)
MS / FAB: 633.78 (M + )

[합성예 146] 화합물 [146]의 합성[Synthesis Example 146] Synthesis of Compound [146]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.54(d. 1H), 8.30(s, 2H), 8.17~8.11(m, 3H), 7.99~7.81(m, 12H), 7.61~7.24(m, 13H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.54 (d. 1H), 8.30 (s, 2H), 8.17 to 8.11 (m, 3H), 7.99 to 7.81 (m, 12H) , 7.61 ~ 7.24 (m, 13H)

MS/FAB: 695.85(M+)
MS / FAB: 695.85 (M + )

[합성예 147] 화합물 [147]의 합성[Synthesis Example 147] Synthesis of compound [147]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.54(d. 1H), 8.30(s, 2H), 8.11(m, 3H), 7.99~7.49(m, 20H), 7.38~7.24(m, 5H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.54 (d. 1H), 8.30 (s, 2H), 8.11 (m, 3H), 7.99 to 7.49 (m, 20H), 7.38 ~ 7.24 (m, 5H)

MS/FAB: 695.85(M+)
MS / FAB: 695.85 (M + )

[합성예 148] 화합물 [148]의 합성[Synthesis Example 148] Synthesis of Compound [148]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30(s, 2H), 8.11(m, 2H), 7.99~7.68(m, 14H), 7.58~7.24(m, 16H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30 (s, 2H), 8.11 (m, 2H), 7.99-7.68 (m, 14H), 7.58-7.42 (m, 16H)

MS/FAB: 771.94(M+)MS / FAB: 771.94 (M + )

[합성예 149] 화합물 [149]의 합성[Synthesis Example 149] Synthesis of Compound [149]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30(s, 2H), 8.11(m, 2H), 7.99~7.72(m, 10H), 7.61~7.57(m, 4H), 7.45~7.32(m, 4H), 6.94(m, 1H), 6.26(s, 1H), 2.09(s, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30 (s, 2H), 8.11 (m, 2H), 7.99-7.72 (m, 10H), 7.61-7.57 (m, 4H) , 7.45-7.72 (m, 4H), 6.94 (m, 1H), 6.26 (s, 1H), 2.09 (s, 3H)

MS/FAB: 583.72(M+)
MS / FAB: 583.72 (M + )

[합성예 150] 화합물 [150]의 합성[Synthesis Example 150] Synthesis of Compound [150]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.55(m, 1H), 8.30~8.27(m, 4H), 8.11(m, 2H), 7.99~7.38(m, 23H), 7.21(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.55 (m, 1H), 8.30-8.27 (m, 4H), 8.11 (m, 2H), 7.99-7.38 (m, 23H) , 7.21 (m, 2 H)

MS/FAB: 722.87(M+)
MS / FAB: 722.87 (M + )

[합성예 151] 화합물 [151]의 합성[Synthesis Example 151] Synthesis of compound [151]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.55(m, 1H), 8.30~8.27(m, 4H), 8.11~8.08(m, 3H), 7.99~7.72(m, 10H), 7.58~7.38(m, 12H), 7.21(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.55 (m, 1H), 8.30-8.27 (m, 4H), 8.11-8.08 (m, 3H), 7.99-7.72 (m, 10H), 7.58 ~ 7.38 (m, 12H), 7.21 (m, 2H)

MS/FAB: 722.87(M+)
MS / FAB: 722.87 (M + )

[합성예 152] 화합물 [152]의 합성[Synthesis Example 152] Synthesis of Compound [152]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.55(m, 1H), 8.30(s, 2H), 8.11(m, 2H), 7.99~7.72(m, 12H), 7.58~7.38(m, 11H), 7.24~7.21(m, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.55 (m, 1H), 8.30 (s, 2H), 8.11 (m, 2H), 7.99 to 7.72 (m, 12H), 7.58 ~ 7.38 (m, 11H), 7.24-7.21 (m, 4H)

MS/FAB: 722.87(M+)MS / FAB: 722.87 (M + )

[합성예 153] 화합물 [153]의 합성[Synthesis Example 153] Synthesis of compound [153]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.55(m, 1H), 8.30(s, 2H), 8.23(m, 1H), 8.11(m, 2H), 7.99~7.81(m, 9H), 7.72~7.69(m, 2H), 7.58~7.38(m, 13H), 7.21(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.55 (m, 1H), 8.30 (s, 2H), 8.23 (m, 1H), 8.11 (m, 2H), 7.99-7.81 (m, 9H), 7.72-7.69 (m, 2H), 7.58-7.38 (m, 13H), 7.21 (m, 2H)

MS/FAB: 722.87(M+)
MS / FAB: 722.87 (M + )

[합성예 154] 화합물 [154]의 합성[Synthesis Example 154] Synthesis of compound [154]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30(s, 2H), 8.17~8.11(m, 3H), 8.00~7.72(m, 11H), 7.58~7.52(m, 5H), 7.38(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30 (s, 2H), 8.17 to 8.11 (m, 3H), 8.00 to 7.72 (m, 11H), 7.58 to 7.52 (m, 5H), 7.38 (m, 2H)

MS/FAB: 587.73(M+)
MS / FAB: 587.73 (M + )

[합성예 155] 화합물 [155]의 합성[Synthesis Example 155] Synthesis of compound [155]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30(s, 2H), 8.17~8.11(m, 3H), 8.00~7.72(m, 13H), 7.58~7.52(m, 5H), 7.38(m, 2H), 7.24(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30 (s, 2H), 8.17 to 8.11 (m, 3H), 8.00 to 7.72 (m, 13H), 7.58 to 7.52 (m, 5H), 7.38 (m, 2H), 7.24 (m, 2H)

MS/FAB: 663.83(M+)
MS / FAB: 663.83 (M + )

[합성예 156] 화합물 [156]의 합성[Synthesis Example 156] Synthesis of Compound [156]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30(s, 2H), 8.17~8.11(m, 3H), 8.00~7.69(m, 13H), 7.58~7.38(m, 9H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30 (s, 2H), 8.17 to 8.11 (m, 3H), 8.00 to 7.69 (m, 13H), 7.58 to 7.38 (m, 9H)

MS/FAB: 663.83(M+)
MS / FAB: 663.83 (M + )

[합성예 157] 화합물 [157]의 합성[Synthesis Example 157] Synthesis of compound [157]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30~8.27(m, 6H), 8.11(m, 2H), 7.99~7.72(m, 10H), 7.58~7.38(m, 11H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30 to 8.27 (m, 6H), 8.11 (m, 2H), 7.99 to 7.72 (m, 10H), 7.58 to 7.38 (m, 11H)

MS/FAB: 685.81(M+)
MS / FAB: 685.81 (M + )

[합성예 158] 화합물 [158]의 합성[Synthesis Example 158] Synthesis of Compound [158]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30~8.27(m, 5H)8.11~7.72(m, 14H), 7.58~7.38(m, 13H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30-8.27 (m, 5H) 8.11-7.72 (m, 14H), 7.58-7.38 (m, 13H)

MS/FAB: 722.87(M+)
MS / FAB: 722.87 (M + )

[합성예 159] 화합물 [159]의 합성[Synthesis Example 159] Synthesis of Compound [159]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.82(m, 2H), 8.37~8.30(m, 4H), 8.11(m, 2H), 7.99~7.72(m, 10H), 7.64~7.57(m, 6H), 7.38(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.82 (m, 2H), 8.37 to 8.30 (m, 4H), 8.11 (m, 2H), 7.99 to 7.72 (m, 10H) , 7.64-7.57 (m, 6H), 7.38 (m, 2H)

MS/FAB: 632.75(M+)
MS / FAB: 632.75 (M + )

[합성예 160] 화합물 [160]의 합성[Synthesis Example 160] Synthesis of Compound [160]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(d, 2H), 8.02~7.63(m, 17H), 7.49~7.29 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (d, 2H), 8.02-7.63 (m, 17H), 7.49-7.29

(m, 8H)  (m, 8 H)

MS/FAB: 631(M+)
MS / FAB: 631 (M + )

[합성예 161] 화합물 [161]의 합성[Synthesis Example 161] Synthesis of Compound [161]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.41(d, 1H), 8.21(d, 2H), 8.06~7.48(m, 21H), 7.29~7.25(m, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.41 (d, 1H), 8.21 (d, 2H), 8.06 to 7.48 (m, 21H), 7.29 to 7.25 (m, 3H)

MS/FAB: 659(M+)
MS / FAB: 659 (M + )

[합성예 162] 화합물 [162]의 합성[Synthesis Example 162] Synthesis of compound [162]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 4H), 8.6(s, 1H), 8.21(d, 2H), 8.01(m, 4H), 7.90~ 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 4H), 8.6 (s, 1H), 8.21 (d, 2H), 8.01 (m, 4H), 7.90 ~

7.63(m, 14H), 7.49~7.48(m, 3H), 7.29(m, 2H) 7.63 (m, 14H), 7.49-7.48 (m, 3H), 7.29 (m, 2H)

MS/FAB: 682(M+)
MS / FAB: 682 (M + )

[합성예 163] 화합물 [163]의 합성[Synthesis Example 163] Synthesis of compound [163]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.38(m, 1H), 8.27~8.21(m, 3H), 8.02(m, 2H), 7.90~7.72(m, 10H), 7.49~7.44(m, 4H), 7.29(m, 2H), 7.01(t, 1H), 6.76(t, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.38 (m, 1H), 8.27 to 8.21 (m, 3H), 8.02 (m, 2H), 7.90 to 7.72 (m, 10H) , 7.49-7.44 (m, 4H), 7.29 (m, 2H), 7.01 (t, 1H), 6.76 (t, 1H)

MS/FAB: 570(M+)
MS / FAB: 570 (M + )

[합성예 164] 화합물 [164]의 합성[Synthesis Example 164] Synthesis of Compound [164]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.38(d, 1H), 8.27~8.20(m, 5H), 8.02(m, 2H), 7.93~7.63(m, 10H), 7.49~7.44(m, 4H), 7.29(m, 2H), 7.15~7.11(m, 3H), 6.76(t, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.38 (d, 1H), 8.27 to 8.20 (m, 5H), 8.02 (m, 2H), 7.93 to 7.63 (m, 10H) , 7.49-7.44 (m, 4H), 7.29 (m, 2H), 7.15-7.71 (m, 3H), 6.76 (t, 1H)

MS/FAB: 646(M+)
MS / FAB: 646 (M + )

[합성예 165] 화합물 [165]의 합성[Synthesis Example 165] Synthesis of Compound [165]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.38(d, 1H), 8.27~8.21(m, 3H), 8.02(m, 2H), 7.90~7.63(m, 12H), 7.49~7.29(m, 8H), 7.11(t, 1H), 6.76(t, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.38 (d, 1H), 8.27 to 8.21 (m, 3H), 8.02 (m, 2H), 7.90 to 7.63 (m, 12H) , 7.49-7.29 (m, 8H), 7.11 (t, 1H), 6.76 (t, 1H)

MS/FAB: 646(M+)
MS / FAB: 646 (M + )

[합성예 166] 화합물 [166]의 합성[Synthesis Example 166] Synthesis of Compound [166]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.38(d, 1H), 8.21(d, 2H), 8.02(m, 2H), 7.90~ 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.38 (d, 1H), 8.21 (d, 2H), 8.02 (m, 2H), 7.90 ~

7.60(m, 14H), 7.49~7.29(m, 11H), 7.11(t, 1H), 6.76(t, 1H)7.60 (m, 14H), 7.49-7.29 (m, 11H), 7.11 (t, 1H), 6.76 (t, 1H)

MS/FAB: 722(M+)
MS / FAB: 722 (M + )

[합성예 167] 화합물 [167]의 합성[Synthesis Example 167] Synthesis of Compound [167]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.38(d, 1H), 8.21~8.20(m, 4H), 8.02(m, 2H), 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.38 (d, 1H), 8.21-8.20 (m, 4H), 8.02 (m, 2H),

7.90~7.63(m, 10H), 7.49~7.29(m, 11H), 7.15~7.11(m, 3H), 6.76(t, 1H)7.90 ~ 7.63 (m, 10H), 7.49 ~ 7.29 (m, 11H), 7.15 ~ 7.11 (m, 3H), 6.76 (t, 1H)

MS/FAB: 722(M+)
MS / FAB: 722 (M + )

[합성예 168] 화합물 [168]의 합성[Synthesis Example 168] Synthesis of Compound [168]

1H NMR (300 MHz, CDCl3): δ 9.50(s, 1H), 8.83(m, 2H), 8.21(d, 2H), 8.03~8.02(m, 4H), 1 H NMR (300 MHz, CDCl 3 ): δ 9.50 (s, 1H), 8.83 (m, 2H), 8.21 (d, 2H), 8.03 ~ 8.02 (m, 4H),

7.90~7.63(m, 10H), 7.49~7.29(m, 8H), 7.04(m, 1H), 6.83(t, 1H), 6.71(d, 1H)7.90-7.63 (m, 10H), 7.49-7.29 (m, 8H), 7.04 (m, 1H), 6.83 (t, 1H), 6.71 (d, 1H)

MS/FAB: 646(M+)
MS / FAB: 646 (M + )

[합성예 169] 화합물 [169]의 합성[Synthesis Example 169] Synthesis of Compound [169]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(d, 2H), 7.96~7.68(m, 18H), 7.53~7.49 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (d, 2H), 7.96-7.76 (m, 18H), 7.53-7.49

7.49(m, 5H), 7.29(m, 2H)7.49 (m, 5 H), 7.29 (m, 2 H)

MS/FAB: 631(M+)
MS / FAB: 631 (M + )

[합성예 170] 화합물 [170]의 합성[Synthesis Example 170] Synthesis of Compound [170]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.38(d, 1H), 8.21(d, 2H), 8.02(m, 2H), 7.90~ 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.38 (d, 1H), 8.21 (d, 2H), 8.02 (m, 2H), 7.90 ~

7.63(m, 10H), 7.49~7.44(m, 4H), 7.29(m, 2H), 7.11(t, 1H), 6.76(t, 1H), 2.15(s, 3H)7.63 (m, 10H), 7.49-7.44 (m, 4H), 7.29 (m, 2H), 7.11 (t, 1H), 6.76 (t, 1H), 2.15 (s, 3H)

MS/FAB: 584(M+)
MS / FAB: 584 (M + )

[합성예 171] 화합물 [171]의 합성[Synthesis Example 171] Synthesis of Compound [171]

1H NMR (300 MHz, CDCl3): δ 9.16(s, 1H), 8.83(m, 2H), 8.73~8.70(t, 2H), 8.21(d, 2H), 1 H NMR (300 MHz, CDCl 3 ): δ 9.16 (s, 1H), 8.83 (m, 2H), 8.73-8.70 (t, 2H), 8.21 (d, 2H),

8.02(m, 2H), 7.90~7.63(m, 10H), 7.49~7.48(m, 3H), 7.29~7.26(m, 3H)8.02 (m, 2H), 7.90-7.63 (m, 10H), 7.49-7.48 (m, 3H), 7.29-7.26 (m, 3H)

MS/FAB: 571(M+)
MS / FAB: 571 (M + )

[합성예 172] 화합물 [172]의 합성[Synthesis Example 172] Synthesis of Compound [172]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.70(s, 1H), 8.53(m, 3H), 8.21(d, 2H), 8.02 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.70 (s, 1H), 8.53 (m, 3H), 8.21 (d, 2H), 8.02

(m, 2H), 7.90~7.63(m, 10H), 7.49~7.48(m, 3H), 7.29(m, 2H)(m, 2H), 7.90-7.63 (m, 10H), 7.49-7.48 (m, 3H), 7.29 (m, 2H)

MS/FAB: 571(M+)
MS / FAB: 571 (M + )

[합성예 173] 화합물 [173]의 합성[Synthesis Example 173] Synthesis of Compound [173]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.73~8.68(m, 3H), 8.21(d, 2H), 8.02(m, 2H), 7.90~7.63(m, 10H), 7.49~7.48(m, 3H), 7.29(m, 2H), 7.18(t, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.73-8.68 (m, 3H), 8.21 (d, 2H), 8.02 (m, 2H), 7.90-7.63 (m, 10H) , 7.49-7.48 (m, 3H), 7.29 (m, 2H), 7.18 (t, 1H)

MS/FAB: 571(M+)
MS / FAB: 571 (M + )

[합성예 174] 화합물 [174]의 합성[Synthesis Example 174] Synthesis of Compound [174]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.38(d, 1H), 8.21(d, 2H), 8.02(m, 2H), 7.90~ 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.38 (d, 1H), 8.21 (d, 2H), 8.02 (m, 2H), 7.90 ~

7.63(m, 10H), 7.49~7.38(m, 5H), 7.29(m, 2H), 7.11(t, 1H), 6.76(t, 1H)7.63 (m, 10H), 7.49 ~ 7.38 (m, 5H), 7.29 (m, 2H), 7.11 (t, 1H), 6.76 (t, 1H)

MS/FAB: 570(M+)
MS / FAB: 570 (M + )

[합성예 175] 화합물 [175]의 합성[Synthesis Example 175] Synthesis of Compound [175]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.11(m, 1H), 8.30(s, 2H), 8.11(m, 2H), 7.99~7.46(m, 10H), 7.58~7.40(m, 11H), 7.20(m, 1H), 6.85(m, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.11 (m, 1H), 8.30 (s, 2H), 8.11 (m, 2H), 7.99-7.46 (m, 10H), 7.58 ~ 7.40 (m, 11H), 7.20 (m, 1H), 6.85 (m, 1H)

MS/FAB: 646(M+)
MS / FAB: 646 (M + )

[합성예 176] 화합물 [176]의 합성[Synthesis Example 176] Synthesis of Compound [176]

1H NMR (300 MHz, CDCl3): δ 8.89~8.92(m, 3H), 8.67(s, 1H), 8.2(s, 2H), 8.11(m, 2H), 7.99~7.72(m, 10H), 7.58~7.38(m, 10H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.89 to 8.92 (m, 3H), 8.67 (s, 1H), 8.2 (s, 2H), 8.11 (m, 2H), 7.99 to 7.72 (m, 10H) , 7.58 ~ 7.38 (m, 10H)

MS/FAB: 648(M+)
MS / FAB: 648 (M + )

[합성예 177] 화합물 [177]의 합성[Synthesis Example 177] Synthesis of Compound [177]

1H NMR (300 MHz, CDCl3): δ 9.89~8.92(m, 3H), 8.67(s, 1H), 8.30(s, 2H), 8.11(m, 2H), 7.99~7.38(m, 24H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.89 to 8.92 (m, 3H), 8.67 (s, 1H), 8.30 (s, 2H), 8.11 (m, 2H), 7.99 to 7.38 (m, 24H)

MS/FAB: 724(M+)
MS / FAB: 724 (M + )

[합성예 178] 화합물 [178]의 합성[Synthesis Example 178] Synthesis of Compound [178]

1H NMR (300 MHz, CDCl3): δ 8.99(s, 1H), 8.92(m, 2H), 8.67~7.27(m, 4H), 8.11(m, 2H), 7.99~7.40(m, 27H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.99 (s, 1H), 8.92 (m, 2H), 8.67-7.27 (m, 4H), 8.11 (m, 2H), 7.99-7.40 (m, 27H)

MS/FAB: 800(M+)
MS / FAB: 800 (M + )

[합성예 179] 화합물 [179]의 합성[Synthesis Example 179] Synthesis of Compound [179]

1H NMR (300 MHz, CDCl3): δ 8.99(s, 1H), 8.92(m, 2H), 8.67(s, 1H), 8.30(s, 2H), 8.11~8.08(m, 3H), 7.99~7.81(m, 10H), 7.58~7.38(m, 13H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.99 (s, 1H), 8.92 (m, 2H), 8.67 (s, 1H), 8.30 (s, 2H), 8.11 to 8.08 (m, 3H), 7.99 ~ 7.81 (m, 10H), 7.58-7.38 (m, 13H)

MS/FAB: 724(M+)
MS / FAB: 724 (M + )

[합성예 180] 화합물 [180]의 합성[Synthesis Example 180] Synthesis of Compound [180]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30(s, 2H), 8.15~8.11(m, 3H), 7.99~7.78(m, 14H), 7.58~7.38(m, 9H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30 (s, 2H), 8.15 to 8.11 (m, 3H), 7.99 to 7.78 (m, 14H), 7.58 to 7.38 (m, 9H)

MS/FAB: 658(M+)
MS / FAB: 658 (M + )

[합성예 181] 화합물 [181]의 합성[Synthesis Example 181] Synthesis of Compound [181]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30(s, 2H), 8.15~8.11(m, 3H), 7.99~7.76(m, 16H), 7.58~7.50(m, 6H), 7.40~7.38(m, 3H), 7.24(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30 (s, 2H), 8.15 to 8.11 (m, 3H), 7.99 to 7.72 (m, 16H), 7.58 to 7.50 (m, 6H), 7.40 ~ 7.38 (m, 3H), 7.24 (d, 2H)

MS/FAB: 734(M+)
MS / FAB: 734 (M + )

[합성예 182] 화합물 [182]의 합성[Synthesis Example 182] Synthesis of Compound [182]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30~8.27(m, 6H), 8.15~8.11(m, 3H), 7.99~7.82(m, 12H), 7.58~7.50(m, 6H), 7.40~7.38(m, 3H), 7.24(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30-8.27 (m, 6H), 8.15-8.11 (m, 3H), 7.99-7.82 (m, 12H), 7.58-7.50 ( m, 6H), 7.40-7.38 (m, 3H), 7.24 (d, 2H)

MS/FAB: 734(M+)
MS / FAB: 734 (M + )

[합성예 183] 화합물 [183]의 합성[Synthesis Example 183] Synthesis of Compound [183]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.29~8.10(m, 6H), 8.27~8.10(m, 2H), 7.99~7.72(m, 10H), 7.58~7.38(m, 11H), 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.29 to 8.10 (m, 6H), 8.27 to 8.10 (m, 2H), 7.99 to 7.72 (m, 10H), 7.58 to 7.38 ( m, 11H),

MS/FAB: 673(M+)
MS / FAB: 673 (M + )

[합성예 184] 화합물 [184]의 합성[Synthesis Example 184] Synthesis of Compound [184]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30~8.27(m, 6H), 8.11(m, 2H), 7.99(m, 7.38(m, 25H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30-8.27 (m, 6H), 8.11 (m, 2H), 7.99 (m, 7.38 (m, 25H)

MS/FAB: 749(M+)
MS / FAB: 749 (M + )

[합성예 185 화합물 [185]의 합성Synthesis Example 185 Synthesis of Compound [185]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.30~8.27(m, 4H), 8.11(m, 2H), 7.99~7.72(m, 12H), 7.58~7.40(m, 13H), 7.24(d, 2H), 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.30-8.27 (m, 4H), 8.11 (m, 2H), 7.99-7.72 (m, 12H), 7.58-7.40 (m, 13H), 7.24 (d, 2H),

MS/FAB: 749(M+)
MS / FAB: 749 (M + )

[합성예 186] 화합물 [186]의 합성[Synthesis Example 186] Synthesis of Compound [186]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.73(m, 2H), 8.2(s, 2H), 8.11(m, 2H), 7.99~7.72(m, 12H), 7.58~7.24(m, 14H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.73 (m, 2H), 8.2 (s, 2H), 8.11 (m, 2H), 7.99-7.72 (m, 12H), 7.58 ~ 7.24 (m, 14H)

MS/FAB: 734(M+)
MS / FAB: 734 (M + )

[합성예 187] 화합물 [187]의 합성[Synthesis Example 187] Synthesis of Compound [187]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.82~8.77(m,, 2H), 8.30(s, 2H), 8.11(d, 2H), 7.99~7.72(m, 10H), 7.58~7.50(m, 4H), 7.38(m, 2H), 7.27(m, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.82 to 8.77 (m, 2H), 8.30 (s, 2H), 8.11 (d, 2H), 7.99 to 7.72 (m, 10H ), 7.58-7.50 (m, 4H), 7.38 (m, 2H), 7.27 (m, 1H)

MS/FAB: 571(M+)
MS / FAB: 571 (M + )

[합성예 188] 화합물 [188]의 합성[Synthesis Example 188] Synthesis of Compound [188]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.82~8.75(m, 2H), 8.30~8.29(m, 4H), 8.11(d, 2H), 7.99~7.72(m, 10H), 7.58~7.57(m, 3H), 7.50(s, 1H), 7.38(m, 2H), 7.27~7.24(m, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.82 to 8.75 (m, 2H), 8.30 to 8.29 (m, 4H), 8.11 (d, 2H), 7.99 to 7.72 (m, 10H), 7.58-7.57 (m, 3H), 7.50 (s, 1H), 7.38 (m, 2H), 7.27-7.44 (m, 3H)

MS/FAB: 647(M+)
MS / FAB: 647 (M + )

[합성예 189] 화합물 [189]의 합성[Synthesis Example 189] Synthesis of Compound [189]

1H NMR (300 MHz, CDCl3): δ 8.92(m, 2H), 8.82~8.77(m, 2H), 8.30~8.29(m, 4H), 8.11(d, 2H), 7.99~7.67(m, 10H), 7.58~7.38(m, 10H), 7.27~7.24(m, 3H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.92 (m, 2H), 8.82 to 8.77 (m, 2H), 8.30 to 8.29 (m, 4H), 8.11 (d, 2H), 7.99 to 7.07 (m, 10H), 7.58 ~ 7.38 (m, 10H), 7.27 ~ 7.24 (m, 3H)

MS/FAB: 723(M+)
MS / FAB: 723 (M + )

[합성예 190] 화합물 [190]의 합성[Synthesis Example 190] Synthesis of Compound [190]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.50(m, 1H), 8.21(s, 2H), 8.02~7.63(m, 13H), 7.49~7.48(m, 3H), 7.29(m, 2H), 7.17(m, 1H), 7.02(m, 1H), 6.77(m, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.50 (m, 1H), 8.21 (s, 2H), 8.02-7.63 (m, 13H), 7.49-7.48 (m, 3H) , 7.29 (m, 2H), 7.17 (m, 1H), 7.02 (m, 1H), 6.77 (m, 1H)

MS/FAB: 570(M+)
MS / FAB: 570 (M + )

[합성예 191] 화합물 [191]의 합성[Synthesis Example 191] Synthesis of Compound [191]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.50(m, 1H), 8.21(s, 2H), 8.02~7.63(m, 13H), 7.49~7.29(m, 10H), 7.02(m, 1H), 6.77(m, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.50 (m, 1H), 8.21 (s, 2H), 8.02-7.63 (m, 13H), 7.49-7.29 (m, 10H) , 7.02 (m, 1 H), 6.77 (m, 1 H)

MS/FAB: 646(M+)
MS / FAB: 646 (M + )

[합성예 192] 화합물 [192]의 합성[Synthesis Example 192] Synthesis of Compound [192]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.50(m, 1H), 8.21(s, 2H), 8.02~7.63(m, 15H), 7.49~7.48(m, 3H), 7.29(m, 2H), 7.15(m, 3H), 7.02(m, 1H), 6.77(m, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.50 (m, 1H), 8.21 (s, 2H), 8.02-7.63 (m, 15H), 7.49-7.48 (m, 3H) , 7.29 (m, 2H), 7.15 (m, 3H), 7.02 (m, 1H), 6.77 (m, 1H)

MS/FAB: 646(M+)
MS / FAB: 646 (M + )

[합성예 193] 화합물 [193]의 합성[Synthesis Example 193] Synthesis of Compound [193]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.50(m, 1H), 8.21(s, 2H), 8.02~7.63(m, 15H), 7.49~7.29(m, 10H), 7.15(m, 2H), 7.02(m, 1H), 6.77(m, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.50 (m, 1H), 8.21 (s, 2H), 8.02-7.63 (m, 15H), 7.49-7.29 (m, 10H) , 7.15 (m, 2H), 7.02 (m, 1H), 6.77 (m, 1H)

MS/FAB: 722(M+)
MS / FAB: 722 (M + )

[합성예 194] 화합물 [194]의 합성[Synthesis Example 194] Synthesis of Compound [194]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.50(m, 1H), 8.21~8.14(m, 3H), 8.02~7.63(m, 14H), 7.49~7.29(m, 12H), 7.02(m, 1H), 6.77(m, 1H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.50 (m, 1H), 8.21-8.14 (m, 3H), 8.02-7.63 (m, 14H), 7.49-7.29 (m, 12H), 7.02 (m, 1H), 6.77 (m, 1H)

MS/FAB: 722(M+)
MS / FAB: 722 (M + )

[합성예 195] 화합물 [195]의 합성[Synthesis Example 195] Synthesis of Compound [195]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21~8.18(m, 4H), 8.02(m, 2H), 7.99~7.38(m, 32H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21-8.18 (m, 4H), 8.02 (m, 2H), 7.99-7.38 (m, 32H)

MS/FAB: 825(M+)
MS / FAB: 825 (M + )

[합성예 196] 화합물 [196]의 합성 [Synthesis Example 196] Synthesis of Compound [196]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 4H), 8.21(s, 2H), 8.02(m, 4H), 7.99~7.72(m, 16H), 7.49~7.29(m, 10H), 7.15(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 4H), 8.21 (s, 2H), 8.02 (m, 4H), 7.99-7.72 (m, 16H), 7.49-7.29 (m, 10H) , 7.15 (d, 2 H)

MS/FAB: 822(M+)
MS / FAB: 822 (M + )

[합성예 197] 화합물 [197]의 합성 [Synthesis Example 197] Synthesis of Compound [197]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 4H), 8.21~8.14(m, 3H), 8.02(m, 4H), 7.99~7.72(m, 15H), 7.49~7.29(m, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 4H), 8.21 to 8.14 (m, 3H), 8.02 (m, 4H), 7.99 to 7.72 (m, 15H), 7.49 to 7.29 (m, 12H)

MS/FAB: 822(M+)
MS / FAB: 822 (M + )

[합성예 198] 화합물 [198]의 합성 다시Synthesis Example 198 Synthesis of Compound 198 Again

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.46(m, 1H), 8.20~8.18(m, 4H), 8.02(m, 2H), 7.99~7.72(m, 10H), 7.49~7.29(m, 9H), 7.12(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.46 (m, 1H), 8.20-8.18 (m, 4H), 8.02 (m, 2H), 7.99-7.72 (m, 10H) , 7.49-7.29 (m, 9H), 7.12 (m, 2H)

MS/FAB: 646(M+)
MS / FAB: 646 (M + )

[합성예 199] 화합물 [199]의 합성[Preparation Example 199] Synthesis of compound [199]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.03~8.02(m, 3H), 7.99~7.72(m, 3H), 7.60~7.40(m, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.03 to 8.02 (m, 3H), 7.99 to 7.72 (m, 3H), 7.60 to 7.40 (m, 12H)

MS/FAB: 656(M+)
MS / FAB: 656 (M + )

[합성예 200] 화합물 [200]의 합성[Synthesis Example 200] Synthesis of Compound [200]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.03~8.02(m, 3H), 7.99~7.72(m, 17H), 7.60~7.57(m, 10H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.03 to 8.02 (m, 3H), 7.99 to 7.72 (m, 17H), 7.60 to 7.57 (m, 10H)

MS/FAB: 706(M+)
MS / FAB: 706 (M + )

[합성예 201] 화합물 [201]의 합성[Synthesis Example 201] Synthesis of Compound [201]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.03~8.02(m, 3H), 7.99~7.72(m, 13H), 7.60~7.40(m, 12H), 7.15(d, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.03 to 8.02 (m, 3H), 7.99 to 7.72 (m, 13H), 7.60 to 7.40 (m, 12H), 7.15 (d, 4H)

MS/FAB: 732(M+)
MS / FAB: 732 (M + )

[합성예 202] 화합물 [202]의 합성[Synthesis Example 202] Synthesis of Compound [202]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.02~7.48(m, 21H), 7.10(m, 4H), 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.02-7.48 (m, 21H), 7.10 (m, 4H),

7.02(s, 1H), 6.73~6.71(m, 3H), 6.53(m, 4H) 7.02 (s, 1H), 6.73 ~ 6.71 (m, 3H), 6.53 (m, 4H)

MS/FAB: 747(M+)
MS / FAB: 747 (M + )

[합성예 203] 화합물 [203]의 합성[Synthesis Example 203] Synthesis of Compound [203]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.02(m, 2H), 7.99~7.72(m, 13H), 7.49~7.48(m, 6H), 7.02~6.97(m, 5H), 6.73(m, 1H), 6.45~6.41(m, 4H), 2.24(s, 3H), 1.25(m, 9H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.02 (m, 2H), 7.99-7.72 (m, 13H), 7.49-7.48 (m, 6H) , 7.02-6.97 (m, 5H), 6.73 (m, 1H), 6.45-6.61 (m, 4H), 2.24 (s, 3H), 1.25 (m, 9H)

MS/FAB: 818(M+)
MS / FAB: 818 (M + )

[합성예 204] 화합물 [204]의 합성[Preparation 204] Synthesis of Compound [204]

1H NMR (300 MHz, CDCl3): δ 8.83(m, 2H), 8.21(s, 2H), 8.02(m, 2H), 7.99~7.72(m, 14H), 7.61~7.57(m, 8H), 7.28~7.10(m, 4H), 7.02(s, 1H), 6.73~6.65(m, 3H), 6.53~6.48(m, 3H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (m, 2H), 8.21 (s, 2H), 8.02 (m, 2H), 7.99-7.72 (m, 14H), 7.61-7.57 (m, 8H) , 7.28-7.10 (m, 4H), 7.02 (s, 1H), 6.73-6.65 (m, 3H), 6.53-6.68 (m, 3H), 1.62 (s, 6H)

MS/FAB: 864(M+)
MS / FAB: 864 (M + )

[합성예 205] 화합물 [205]의 합성[Synthesis Example 205] Synthesis of compound [205]

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H) 8.00~7.73(m, 14H), 7.62~7.38(m, 16H), 7.28(m, 1H), 7.03(s, 1H), 6.85(d, 1H), 6.75~6.69(m, 3H), 6.58(s, 1H), 1.72(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H) 8.00 ~ 7.73 (m, 14H), 7.62 ~ 7.38 (m, 16H), 7.28 (m, 1H), 7.03 (s, 1H), 6.85 (d, 1H), 6.75-6.69 (m, 3H), 6.58 (s, 1H), 1.72 (s, 6H)

MS/FAB: 940(M+)
MS / FAB: 940 (M + )

[합성예 206] 화합물 [206]의 합성[Synthesis Example 206] Synthesis of Compound [206]

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.88(m, 6H), 7.39(m, 2H), 7.20(m, 8H), 6.81(m, 4H), 6.63(m, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.88 (m, 6H), 7.39 (m, 2H), 7.20 (m, 8H), 6.81 (m, 4H), 6.63 (m, 8H)

MS/FAB: 662(M+)
MS / FAB: 662 (M + )

[합성예 207] 화합물 [207]의 합성[Synthesis Example 207] Synthesis of Compound [207]

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.88~7.82(m, 6H), 7.39(m, 2H), 7.20(m, 4H), 6.98(d, 4H), 6.81(m, 2H), 6.63(d, 4H), 6.51(d, 4H), 2.34(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.88-7.82 (m, 6H), 7.39 (m, 2H), 7.20 (m, 4H), 6.98 (d, 4H), 6.81 (m, 2H), 6.63 (d, 4H), 6.51 (d, 4H), 2.34 (s, 6H)

MS/FAB: 690(M+)
MS / FAB: 690 (M + )

[합성예 208] 화합물 [208] 합성Synthesis Example 208 Synthesis of Compound

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 2H), 7.20(m, 4H), 7.08(m, 2H), 6.81(m, 2H), 6.63~6.55(m, 8H), 6.44(d, 2H), 2.34(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 2H), 7.20 (m, 4H), 7.08 (m, 2H), 6.81 (m, 2H), 6.63-6.65 (m, 8H), 6.44 (d, 2H), 2.34 (s, 6H)

MS/FAB: 690(M+)
MS / FAB: 690 (M + )

[합성예 209] 화합물 [209] 합성Synthesis Example 209 Compound [209] Synthesis

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 2H), 7.20~7.15(m, 6H), 7.01(m, 2H), 6.81(m, 2H), 6.69~6.63(m, 6H), 6.51(d, 2H), 2.12(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 2H), 7.20 ~ 7.15 (m, 6H), 7.01 (m, 2H), 6.81 (m, 2H), 6.69-6.63 (m, 6H), 6.51 (d, 2H), 2.12 (s, 6H)

MS/FAB: 690(M+)
MS / FAB: 690 (M + )

[합성예 210] 화합물 [210] 합성Synthesis Example 210 Compound [210] Synthesis

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 2H), 6.98(m, 8H), 6.51(d, 8H), 2.34(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 2H), 6.98 (m, 8H), 6.51 (d, 8H), 2.34 (s, 12H)

MS/FAB: 718(M+)
MS / FAB: 718 (M + )

[합성예 211] 화합물 [211] 합성Synthesis Example 211 Compound [211] Synthesis

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 2H), 7.08(m, 4H), 6.59~6.55(m, 8H), 6.44(d, 4H), 2.34(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 2H), 7.08 (m, 4H), 6.59-6.55 (m, 8H), 6.44 (d, 4H), 2.34 (s, 12H)

MS/FAB: 718(M+)
MS / FAB: 718 (M + )

[합성예 212] 화합물 [212] 합성Synthesis Example 212 Compound [212] Synthesis

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 2H), 7.08(m, 2H), 6.98(d, 4H), 6.59~6.44(m, 10H), 2.34(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 2H), 7.08 (m, 2H), 6.98 (d, 4H), 6.59-6.44 (m, 10H), 2.34 (s, 12H)

MS/FAB: 718(M+)
MS / FAB: 718 (M + )

[합성예 213] 화합물 [213] 합성Synthesis Example 213 Synthesis of Compound

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 2H), 7.05(d, 8H), 6.55(d, 8H), 2.87(m, 4H), 1.20(d, 24H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 2H), 7.05 (d, 8H), 6.55 (d, 8H), 2.87 (m, 4H), 1.20 (d, 24H)

MS/FAB: 831(M+)
MS / FAB: 831 (M + )

[합성예 214] 화합물 [214] 합성Synthesis Example 214 Synthesis of Compound

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 2H), 7.01(d, 8H), 6.55(d, 8H), 1.35(s, 36H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 2H), 7.01 (d, 8H), 6.55 (d, 8H), 1.35 (s, 36H)

MS/FAB: 887(M+)
MS / FAB: 887 (M + )

[합성예 215] 화합물 [215] 합성Synthesis Example 215 Compound [215] Synthesis

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 2H), 7.05~7.01(m, 8H), 6.55(d, 8H), 2.87(m, 2H), 1.35(s, 18H), 1.20(d, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 2H), 7.05 ~ 7.01 (m, 8H), 6.55 (d, 8H), 2.87 (m, 2H), 1.35 (s, 18H), 1.20 (d, 12H)

MS/FAB: 859(M+)
MS / FAB: 859 (M < + & gt ; ).

[합성예 216] 화합물 [216] 합성Synthesis Example 216 Synthesis of Compound

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 6H), 7.20(m, 4H), 6.81(m, 6H), 6.63(d, 4H), 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 6H), 7.20 (m, 4H), 6.81 (m, 6H), 6.63 (d, 4H),

MS/FAB: 712(M+)
MS / FAB: 712 (M + )

[합성예 217] 화합물 [217] 합성Synthesis Example 217 Compound [217] Synthesis

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.82(m, 6H), 7.39(m, 2H), 7.20(m, 4H), 6.99(m, 4H), 6.81(m, 2H), 6.63~6.61(m, 8H), 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.82 (m, 6H), 7.39 (m, 2H), 7.20 (m, 4H), 6.99 (m, 4H), 6.81 (m, 2H), 6.63-6.61 (m, 8H),

MS/FAB: 698(M+)
MS / FAB: 698 (M + )

[합성예 218] 화합물 [218] 합성Synthesis Example 218 Compound [218] Synthesis

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12~8.02(m, 6H), 7.91~7.82(m, 6H), 7.57~7.53(m, 6H), 7.39~7.38(m, 4H), 7.20(m, 4H), 6.98(d, 2H), 6.81(m, 2H), 6.63(d, 4H), 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 to 8.02 (m, 6H), 7.91 to 7.82 (m, 6H), 7.57 to 7.53 (m, 6H), 7.39 ~ 7.38 (m, 4H), 7.20 (m, 4H), 6.98 (d, 2H), 6.81 (m, 2H), 6.63 (d, 4H),

MS/FAB: 762(M+)
MS / FAB: 762 (M + )

[합성예 219] 화합물 [219] 합성Synthesis Example 219 Compound [219] Synthesis

1H NMR (300 MHz, CDCl3): δ 8.93(d, 2H), 8.31(s, 2H), 8.12(d, 2H), 7.91~7.74(m, 14H), 7.50~7.36(m, 8H), 7.20(m, 4H), 6.81(m, 2H), 6.63(d, 4H), 1 H NMR (300 MHz, CDCl 3 ): δ 8.93 (d, 2H), 8.31 (s, 2H), 8.12 (d, 2H), 7.91-7.74 (m, 14H), 7.50-7.36 (m, 8H) , 7.20 (m, 4H), 6.81 (m, 2H), 6.63 (d, 4H),

MS/FAB: 762(M+)
MS / FAB: 762 (M + )

[합성예 220] 화합물 [220]의 합성[Synthesis Example 220] Synthesis of Compound [220]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02~7.92(m, 6H) 7.81~7.64(m, 14H), 7.47~7.26(m, 16H), 6.88(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 ~ 7.92 (m, 6H) 7.81 ~ 7.64 (m, 14H), 7.47 ~ 7.26 (m, 16H ), 6.88 (m, 2H)

MS/FAB: 863(M+)
MS / FAB: 863 (M < + & gt ; ).

[합성예 221] 화합물 [221]의 합성[Synthesis Example 221] Synthesis of Compound [221]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.64(m, 22H), 7.40~7.39(m, 8H), 7.29~7.26(m, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81 ~ 7.64 (m, 22H), 7.40 ~ 7.39 (m, 8H) , 7.29-7.26 (m, 6H)

MS/FAB: 863(M+)
MS / FAB: 863 (M < + & gt ; ).

[합성예 222] 화합물 [222]의 합성[Synthesis Example 222] Synthesis of Compound [222]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.44~7.31(m, 30H), 6.59(d, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.44-7.31 (m, 30H) , 6.59 (d, 8 H)

MS/FAB: 967(M+)
MS / FAB: 967 (M + )

[합성예 223] 화합물 [223]의 합성[Synthesis Example 223] Synthesis of compound [223]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.44~7.31(m, 16H), 7.10(m, 4H), 6.71(m, 2H), 6.59~6.53(m, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.44-7.31 (m, 16H) , 7.10 (m, 4H), 6.71 (m, 2H), 6.59-6.63 (m, 8H)

MS/FAB: 815(M+)
MS / FAB: 815 (M + )

[합성예 224] 화합물 [224]의 합성[Synthesis Example 224] Synthesis of compound [224]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.44~7.31(m, 16H), 6.88(t, 4H), 6.59(d, 4H), 6.41(d, 4H), 2.24(s, 6H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.44-7.31 (m, 16H) , 6.88 (t, 4H), 6.59 (d, 4H), 6.41 (d, 4H), 2.24 (s, 6H)

MS/FAB: 843(M+)
MS / FAB: 843 (M + )

[합성예 225] 화합물 [225]의 합성[Synthesis Example 225] Synthesis of Compound [225]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 8H), 7.52~7.45(m, 4H), 7.29~7.28(m, 4H), 7.18~7.10(m, 6H), 6.71~6.65(m, 4H), 6.53~6.48(m, 6H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 8H), 7.52-7.45 (m, 4H) , 7.29 ~ 7.28 (m, 4H), 7.18 ~ 7.10 (m, 6H), 6.71 ~ 6.65 (m, 4H), 6.53 ~ 6.48 (m, 6H), 1.62 (s, 12H)

MS/FAB: 895(M+)
MS / FAB: 895 (M + )

[합성예 226] 화합물 [226]의 합성[Synthesis Example 226] Synthesis of Compound [226]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 8H), 7.52~7.45(m, 4H), 7.29~7.28(m, 4H), 7.18(m, 2H), 6.88(t, 4H), 6.65(s, 2H), 6.48~6.41(m, 6H), 2.24(s, 6H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 8H), 7.52-7.45 (m, 4H) , 7.29-7.28 (m, 4H), 7.18 (m, 2H), 6.88 (t, 4H), 6.65 (s, 2H), 6.48-6.61 (m, 6H), 2.24 (s, 6H), 1.62 (s , 12H)

MS/FAB: 923(M+)MS / FAB: 923 (M + )

[합성예 227] 화합물 [227]의 합성[Synthesis Example 227] Synthesis of compound [227]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.64(m, 16H), 7.52~7.39(m, 8H), 7.28~7.18(m, 8H), 6.65(s, 2H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.74 (m, 16H), 7.52-7.39 (m, 8H) , 7.28 ~ 7.18 (m, 8H), 6.65 (s, 2H), 6.48 (d, 2H), 1.62 (s, 12H)

MS/FAB: 995(M+)
MS / FAB: 995 (M + )

[합성예 228] 화합물 [228]의 합성[Synthesis Example 228] Synthesis of compound [228]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02~7.92(m, 6H), 7.81~7.72(m, 8H), 7.52~7.43(m, 10H), 7.29~7.28(m, 6H), 7.18(m, 2H), 6.88(t, 2H), 6.65(s, 2H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 to 7.92 (m, 6H), 7.81 to 7.72 (m, 8H), 7.52 to 7.43 (m, 10H), 7.29-7.28 (m, 6H), 7.18 (m, 2H), 6.88 (t, 2H), 6.65 (s, 2H), 6.48 (d, 2H), 1.62 (s, 12H)

MS/FAB: 995(M+)
MS / FAB: 995 (M + )

[합성예 229] 화합물 [229]의 합성Synthesis Example 229 Synthesis of Compound [229]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 8H), 7.52~7.28(m, 22H), 7.18(m, 2H), 6.65~6.59(m, 6H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 8H), 7.52-7.28 (m, 22H) , 7.18 (m, 2H), 6.65 to 6.59 (m, 6H), 6.48 (d, 2H), 1.62 (s, 12H)

MS/FAB: 1047(M+)
MS / FAB: 1047 (M + )

[합성예 230] 화합물 [230]의 합성Synthesis Example 230 Synthesis of Compound [230]

1H NMR (300 MHz, CDCl3): δ 9.14(d, 2H), 8.83(d, 2H), 8.60(d, 2H), 8.32(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 8H), 7.52~7.44(m, 10H), 7.29~7.28(m, 4H), 7.18(m, 2H), 6.65~6.59(m, 6H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.14 (d, 2H), 8.83 (d, 2H), 8.60 (d, 2H), 8.32 (d, 2H), 8.21 (s, 2H), 8.02 (d , 2H), 7.81-7.72 (m, 8H), 7.52-7.44 (m, 10H), 7.29-7.28 (m, 4H), 7.18 (m, 2H), 6.65-6.59 (m, 6H), 6.48 (d , 2H), 1.62 (s, 12H)

MS/FAB: 1049(M+)
MS / FAB: 1049 (M + )

[합성예 231] 화합물 [231]의 합성Synthesis Example 231 Synthesis of Compound [231]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.40(d, 2H), 8.21(s, 2H), 8.02~7.95(m, 6H), 7.81~7.72(m, 8H), 7.52~7.41(m, 6H), 7.29~7.28(m, 4H), 7.18~7.16(m, 4H), 6.90(t, 2H), 6.65~6.62(m, 6H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.40 (d, 2H), 8.21 (s, 2H), 8.02-7.95 (m, 6H), 7.81-7.72 (m, 8H) , 7.52 ~ 7.41 (m, 6H), 7.29 ~ 7.28 (m, 4H), 7.18 ~ 7.16 (m, 4H), 6.90 (t, 2H), 6.65 ~ 6.62 (m, 6H), 6.48 (d, 2H) , 1.62 (s, 12H)

MS/FAB: 1049(M+)
MS / FAB: 1049 (M + )

[합성예 232] 화합물 [232]의 합성Synthesis Example 232 Synthesis of Compound [232]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.65(d, 4H), 8.21(s, 2H), 8.02(d, 2H), 7.89~7.72(m, 12H), 7.52~7.44(m, 8H), 7.29~7.28(m, 4H), 7.18(m, 2H), 6.65~6.59(m, 6H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.65 (d, 4H), 8.21 (s, 2H), 8.02 (d, 2H), 7.89 to 7.72 (m, 12H), 7.52 ~ 7.44 (m, 8H), 7.29-7.28 (m, 4H), 7.18 (m, 2H), 6.65-6.59 (m, 6H), 6.48 (d, 2H), 1.62 (s, 12H)

MS/FAB: 1049(M+)
MS / FAB: 1049 (M + )

[합성예 233] 화합물 [233]의 합성Synthesis Example 233 Synthesis of Compound [233]

1H NMR (300 MHz, CDCl3): δ 9.12(s, 2H), 8.90(s, 4H), 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 8H), 7.52~7.44(m, 8H), 7.29~7.28(m, 4H), 7.18(m, 2H), 6.65~6.59(m, 6H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 9.12 (s, 2H), 8.90 (s, 4H), 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81 ~ 7.72 (m, 8H), 7.52-7.44 (m, 8H), 7.29-7.28 (m, 4H), 7.18 (m, 2H), 6.65-6.59 (m, 6H), 6.48 (d, 2H), 1.62 (s , 12H)

MS/FAB: 1051(M+)
MS / FAB: 1051 (M + )

[합성예 234] 화합물 [234]의 합성Synthesis Example 234 Synthesis of Compound [234]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.76(d, 4H), 8.21(s, 2H), 8.02(d, 2H), 7.8~7.72(m, 12H), 7.52~7.45(m, 4H), 7.29~7.18(m, 8H), 6.65~6.59(m, 6H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.76 (d, 4H), 8.21 (s, 2H), 8.02 (d, 2H), 7.8 ~ 7.72 (m, 12H), 7.52 ~ 7.45 (m, 4H), 7.29-7.18 (m, 8H), 6.65-6.59 (m, 6H), 6.48 (d, 2H), 1.62 (s, 12H)

MS/FAB: 1051(M+)
MS / FAB: 1051 (M + )

[합성예 235] 화합물 [235]의 합성Synthesis Example 235 Synthesis of Compound [235]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21~8.20(m, 6H), 8.02(d, 2H), 7.89(, 2H), 7.81~7.72(m, 8H), 7.52~7.28(m, 16H), 7.18(t, 2H), 6.72(d, 2H), 6.65(s, 2H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21-8.20 (m, 6H), 8.02 (d, 2H), 7.89 (, 2H), 7.81-7.72 (m, 8H), 7.52 to 7.28 (m, 16H), 7.18 (t, 2H), 6.72 (d, 2H), 6.65 (s, 2H), 6.48 (d, 2H), 1.62 (s, 12H)

MS/FAB: 1049(M+)MS / FAB: 1049 (M + )

[합성예 236] 화합물 [236]의 합성Synthesis Example 236 Synthesis of Compound

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.23~8.02(s, 4H), 8.02(d, 2H) 7.81~7.72(m, 8H), 7.56~7.28(m, 20H), 6.66(m, 4H), 7.18(t, 2H)6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.23 to 8.02 (s, 4H), 8.02 (d, 2H) 7.81 to 7.72 (m, 8H), 7.56 to 7.28 (m, 20H ), 6.66 (m, 4H), 7.18 (t, 2H) 6.68 (d, 2H), 1.62 (s, 12H)

MS/FAB: 1049(M+)
MS / FAB: 1049 (M + )

[합성예 237] 화합물 [237]의 합성Synthesis Example 237 Synthesis of Compound [237]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.29(s, 4H), 8.21~8.18(m, 6H), 8.02(d, 2H), 7.81~7.72(m, 8H), 7.52~7.41(m, 8H), 7.31~7.28(m, 6H), 7.18(t, 2H), 6.65(s, 2H), 6.48(d, 2H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.29 (s, 4H), 8.21-8.18 (m, 6H), 8.02 (d, 2H), 7.81-7.72 (m, 8H) , 7.52 to 7.41 (m, 8H), 7.31 to 7.28 (m, 6H), 7.18 (t, 2H), 6.65 (s, 2H), 6.48 (d, 2H), 1.62 (s, 12H)

MS/FAB: 1050(M+)
MS / FAB: 1050 (M + )

[합성예 238] 화합물 [238]의 합성Synthesis Example 238 Synthesis of Compound [238]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(t, 2H), 6.95~6.92(m, 8H), 6.63(t, 4H), 6.45(d, 4H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (t, 2H), 6.95 ~ 6.92 (m, 8H), 6.63 (t, 4H), 6.45 (d, 4H), 1.62 (s, 12H)

MS/FAB: 742(M+)
MS / FAB: 742 (M + )

[합성예 239] 화합물 [239]의 합성Synthesis Example 239 Synthesis of Compound [239]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(t, 2H), 6.82(s, 4H), 6.70(d, 4H), 6.33(d, 4H), 2.24(s, 12H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (t, 2H), 6.82 (s, 4H), 6.70 (d, 4H), 6.33 (d, 4H), 2.24 (s, 12H), 1.62 (s, 12H)

MS/FAB: 799(M+)
MS / FAB: 799 (M + )

[합성예 240] 화합물 [240]의 합성Synthesis Example 240 Synthesis of Compound [240]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 10H), 7.52~7.45(m, 8H), 7.28(m, 6H), 7.18(t, 4H), 6.65(s, 4H), 6.48(m, 4H), 1.62(s, 24H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 10H), 7.52-7.45 (m, 8H) , 7.28 (m, 6H), 7.18 (t, 4H), 6.65 (s, 4H), 6.48 (m, 4H), 1.62 (s, 24H)

MS/FAB: 1127(M+)
MS / FAB: 1127 (M + )

[합성예 241] 화합물 [241]의 합성Synthesis Example 241 Synthesis of Compound [241]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(t, 2H), 7.05~7.04(m, 4H), 6.62(t, 2H), 6.45(d, 2H), 4.04(t, 4H), 2.95(t, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (t, 2H), 7.05 ~ 7.04 (m, 4H), 6.62 (t, 2H), 6.45 (d, 2H), 4.04 (t, 4H), 2.95 (t, 4H)

MS/FAB: 563(M+)
MS / FAB: 563 (M + )

[합성예 242] 화합물 [242]의 합성Synthesis Example 242 Synthesis of Compound

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.20(s, 2H), 8.02(d, 2H), 7.84~7.72(m, 10H), 7.50(d, 2H), 7.29~7.23(m, 4H), 6.77(t, 2H), 6.42(d, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.20 (s, 2H), 8.02 (d, 2H), 7.84-7.72 (m, 10H), 7.50 (d, 2H), 7.29 ~ 7.23 (m, 4H), 6.77 (t, 2H), 6.42 (d, 2H)

MS/FAB: 559(M+)
MS / FAB: 559 (M + )

[합성예 243] 화합물 [243]의 합성Synthesis Example 243 Synthesis of Compound [243]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.36(d, 4H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(t, 2H), 7.10(t, 4H), 6.89(d, 4H), 7.71(t, 2H), 6.53(d, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.36 (d, 4H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (t, 2H), 7.10 (t, 4H), 6.89 (d, 4H), 7.71 (t, 2H), 6.53 (d, 4H)

MS/FAB: 665(M+)
MS / FAB: 665 (M + )

[합성예 244] 화합물 [244]의 합성Synthesis Example 244 Synthesis of Compound [244]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02~7.94(m, 6H), 7.81~7.72(m, 6H), 7.26~7.1(m, 10H), 7.71(t, 2H), 6.53(d, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 to 7.94 (m, 6H), 7.81 to 7.72 (m, 6H), 7.26 to 7.1 (m, 10H), 7.71 (t, 2H), 6.53 (d, 4H)

MS/FAB: 665(M+)
MS / FAB: 665 (M + )

[합성예 245] 화합물 [245]의 합성Synthesis Example 245 Synthesis of Compound [245]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02~7.97(m, 4H), 7.78~7.72(m, 6H), 7.45(t, 2H), 7.29(t, 2H), 7.1(t, 4H), 6.71(t, 2H), 6.60~6.52(m, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 to 7.97 (m, 4H), 7.78 to 7.72 (m, 6H), 7.45 (t, 2H) , 7.29 (t, 2H), 7.1 (t, 4H), 6.71 (t, 2H), 6.60 ~ 6.52 (m, 8H)

MS/FAB: 665(M+)
MS / FAB: 665 (M + )

[합성예 246] 화합물 [246]의 합성Synthesis Example 246 Synthesis of Compound [246]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.36(d, 8H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 6H), 7.29(d, 2H), 6.89(d, 8H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.36 (d, 8H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 6H), 7.29 (d, 2H), 6.89 (d, 8H)

MS/FAB: 667(M+)
MS / FAB: 667 (M + )

[합성예 247] 화합물 [247]의 합성Synthesis Example 247 Synthesis of Compound [247]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 8H), 7.29~7.1(m, 12H), 7.71(t, 2H), 6.97(t, 2H), 6.71(t, 2H), 6.53(m, 4H), 6.29(m, 2H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 8H), 7.29-7.1 (m, 12H) , 7.71 (t, 2H), 6.97 (t, 2H), 6.71 (t, 2H), 6.53 (m, 4H), 6.29 (m, 2H)

MS/FAB: 843(M+)
MS / FAB: 843 (M + )

[합성예 248] 화합물 [248]의 합성Synthesis Example 248 Synthesis of Compound [248]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.35(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 10H), 7.42~7.40(t, 4H), 7.29(t, 2H) 7.17~7.10(t, 6H), 6.76~6.71(m, 4H), 6.53(d, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.35 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 10H), 7.42 ~ 7.40 (t, 4H), 7.29 (t, 2H) 7.17-7.10 (t, 6H), 6.76-6.71 (m, 4H), 6.53 (d, 4H)

MS/FAB: 874(M+)
MS / FAB: 874 (M + )

[합성예 249] 화합물 [249]의 합성Synthesis Example 249 Synthesis of Compound [249]

1H NMR (300 MHz, CDCl3): δ 8.83(d, 2H), 8.45(d, 2H), 8.21(s, 2H), 8.02(d, 2H), 7.81~7.72(m, 8H), 7.48~7.10(m, 22H), 6.71~6.65(m, 6H), 6.53(d, 4H) 1 H NMR (300 MHz, CDCl 3 ): δ 8.83 (d, 2H), 8.45 (d, 2H), 8.21 (s, 2H), 8.02 (d, 2H), 7.81-7.72 (m, 8H), 7.48 ~ 7.10 (m, 22H), 6.71-6.65 (m, 6H), 6.53 (d, 4H)

MS/FAB: 992(M+)
MS / FAB: 992 (M + )

비교예 1: 유기 전기발광 소자의 제조Comparative Example 1: Fabrication of Organic Electroluminescent Device

하기 화학식 a로 표시되는 화합물 a를 형광 녹색 호스트로 사용하고, 하기 화학식 c로 표시되는 화합물을 형광 녹색 도판트로 사용하고, 2-TNATA(4,4’,4”-tris(N-naphthalen-2-yl)-N-phenylamino)-triphenylamine)을 정공주입층 물질로 사용하고, α-NPD(N,N’-di(naphthalene-1-yl)-N,N’-diphenylbenzidine)을 정공수송층 물질로 사용하여, 다음과 같은 구조를 갖는 유기발광소자를 제작하였다: ITO/2-TNATA(80nm)/α-NPD(30nm)/화합물a+화합물c(30nm)/Alq3(30nm)/LiF(0.5nm)/ Al(60nm).Using compound a represented by the following formula a as a fluorescent green host, and a compound represented by the following formula c as a fluorescent green dopant, 2-TNATA (4,4 ', 4 ”-tris (N-naphthalen-2 -yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Using the same structure, an organic light emitting device was manufactured: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound a + Compound c (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) / Al (60 nm).

애노드는 코닝(Corning)사의 15Ω/cm2 (1000Å) ITO 유리 기판을 50mm x 50mm x 0.7mm 크기로 잘라서 아세톤 이소프로필 알콜과 순수물 속에서 각 15분 동안 초음파 세정한 후, 30분 동안 UV 오존 세정하여 사용하였다. 상기 기판 상부에 2-TANATA를 진공 증착하여 80nm 두께의 정공주입층을 형성하였다. 상기 정공주입층 상부에, α-NPD를 진공 증착하여 30nm 두께의 정공수송층을 형성하였다. 상기 정공수송층 상부에 화학식 a로 표시되는 화합물 a 및 화학식 c로 표시되는 화합물 c(3% 도핑)를 진공 증착하여 30nm두께의 발광층을 형성하였다. 이후, 상기 발광층 상부에 Alq3(화학식 d) 화합물을 30nm의 두께로 진공증착하여 전자수송층을 형성하였다. 상기 전자수송층 상부에 LiF 0.5nm(전자주입층)과 Al 60nm(캐소드)를 순차적으로 진공증착하여, 하기 표 2에 표시된 바와 같은 유기발광소자를 제조하였다. 이를 비교샘플 1로 칭한다.
Anode cuts Corning's 15Ω / cm 2 (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound a represented by Formula a and Compound c (3% doped) represented by Formula c were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Subsequently, an Alq3 compound (d) was vacuum deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device as shown in Table 2 below. This is called Comparative Sample 1.

비교예 2: 유기 전기발광 소자의 제조Comparative Example 2: Fabrication of Organic Electroluminescent Device

하기 화학식 b로 표시되는 화합물 b를 형광 녹색 호스트로 사용하고, 하기 화학식 c로 표시되는 화합물을 형광 녹색 도판트로 사용하고, 2-TNATA(4,4’,4”-tris(N-naphthalen-2-yl)-N-phenylamino)-triphenylamine)을 정공주입층 물질로 사용하고, α-NPD(N,N’-di(naphthalene-1-yl)-N,N’-diphenylbenzidine)을 정공수송층 물질로 사용하여, 다음과 같은 구조를 갖는 유기발광소자를 제작하였다: ITO/2-TNATA(80nm)/α-NPD(30nm)/화합물b+화합물c(30nm)/Alq3(30nm)/LiF(0.5nm)/ Al(60nm).Using compound b represented by the following formula b as a fluorescent green host, using a compound represented by the following formula c as a fluorescent green dopant, 2-TNATA (4,4 ', 4 ”-tris (N-naphthalen-2 -yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Using the same structure, an organic light emitting device was manufactured: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound b + Compound c (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) / Al (60 nm).

애노드는 코닝(Corning)사의 15Ω/cm2 (1000Å) ITO 유리 기판을 50mm x 50mm x 0.7mm 크기로 잘라서 아세톤 이소프로필 알콜과 순수물 속에서 각 15분 동안 초음파 세정한 후, 30분 동안 UV 오존 세정하여 사용하였다. 상기 기판 상부에 2-TANATA를 진공 증착하여 80nm 두께의 정공주입층을 형성하였다. 상기 정공주입층 상부에, α-NPD를 진공 증착하여 30nm 두께의 정공수송층을 형성하였다. 상기 정공수송층 상부에 화학식 b로 표시되는 화합물 b 및 화학식 c로 표시되는 화합물 c(3% 도핑)를 진공 증착하여 30nm두께의 발광층을 형성하였다. 이후, 상기 발광층 상부에 Alq3(화학식 d) 화합물을 30nm의 두께로 진공증착하여 전자수송층을 형성하였다. 상기 전자수송층 상부에 LiF 0.5nm(전자주입층)과 Al 60nm(캐소드)를 순차적으로 진공증착하여, 하기 표 2에 표시된 바와 같은 유기발광소자를 제조하였다. 이를 비교샘플 2이라고 칭한다.Anode cuts Corning's 15Ω / cm 2 (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound b represented by formula b and compound c represented by formula c (3% doping) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Subsequently, an Alq3 compound (d) was vacuum deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device as shown in Table 2 below. This is called comparative sample 2.

Figure pat00128
Figure pat00128

Figure pat00129

Figure pat00129

실시예 1~112: 유기 전기발광 소자의 제조Examples 1 to 112: Fabrication of Organic Electroluminescent Device

상기 비교예 1 중, 발광층 형광 호스트 화합물로서 화합물 a 대신 상기 합성예에 개시된 화학식 1~109, 199~201로 표시되는 화합물을 발광층 형광 녹색 호스트 화합물로 각각 이용한 것을 제외하고는 상기 비교예 1과 동일한 방법으로 ITO/2-TNATA(80nm)/α-NPD(30nm)/[형광 녹색 호스트 화합물 1~109, 199~201중 하나+화합물c(3%)](30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)의 구조를 갖는 유기발광소자를 제조하였다. 이를 각각 샘플 1 내지 112라고 칭한다.
In Comparative Example 1, the compound represented by Chemical Formulas 1 to 109 and 199 to 201 disclosed in Synthesis Example as a light emitting layer fluorescent green host compound was used instead of Compound a as the light emitting layer fluorescent host compound. ITO / 2-TNATA (80nm) / α-NPD (30nm) / [Fluorescent Green Host Compound 1 ~ 109, 199 ~ 201 + Compound c (3%)] (30nm) / Alq3 (30nm) / LiF An organic light emitting diode having a structure of (0.5 nm) / Al (60 nm) was manufactured. These are referred to as samples 1 to 112, respectively.

평가예 1: 비교샘플 1,2 및 샘플 1~112의 발광 특성 평가Evaluation Example 1 Evaluation of Luminescence Characteristics of Comparative Samples 1 and 2 and Samples 1 to 112

비교샘플 1,2 및 샘플 1~112에 대하여, Keithley sourcemeter “2400”, KONIKA MINOLTA “CS-2000”을 이용하여 발광휘도, 발광효율, 발광피크를 각각 평가하여, 그 결과를 하기 [제1표군]에 나타내었다. 상기 샘플들은 516~524nm 범위에서 녹색 발광 피크값을 보여주었다.
For Comparative Samples 1 and 2 and Samples 1 to 112, the luminous intensity, luminous efficiency, and luminous peak were evaluated using Keithley sourcemeter “2400” and KONIKA MINOLTA “CS-2000”, respectively. ]. The samples showed green emission peaks in the range of 516-524 nm.

[제1표군][First vote group]

Figure pat00130
Figure pat00130

Figure pat00131

Figure pat00131

Figure pat00132

Figure pat00132

Figure pat00133

Figure pat00133

Figure pat00134

Figure pat00134

상기 [제1표군]에 보여지는 바와 같이 샘플 1 내지 112는 비교샘플 1,2에 비하여 향상된 발광 특성을 나타내었다.
As shown in [First Table], Samples 1 to 112 showed improved luminescence properties as compared to Comparative Samples 1,2.

실시예 113 ~ 160: 유기 전기발광 소자의 제조Examples 113 to 160 Fabrication of Organic Electroluminescent Devices

상기 비교예 1 중, 발광층 형광 녹색 도판트 화합물로서 화합물 c 대신 상기 합성예에 개시된 화학식 202~249로 표시되는 화합물을 발광층 형광 녹색 도판트 화합물로 각각 이용한 것을 제외하고는 상기 비교예 1과 동일한 방법으로 ITO/2-TNATA(80nm)/α-NPD(30nm)/[화합물 a+형광 녹색 도판트 화합물 202~249중 하나(3%)](30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)의 구조를 갖는 유기발광소자를 제조하였다. 이를 각각 샘플 113 내지 160이라고 칭한다.
The same method as Comparative Example 1 except for using the compound represented by Formula 202 to 249 disclosed in Synthesis Example as the light emitting layer fluorescent green dopant compound instead of compound c in Comparative Example 1 By ITO / 2-TNATA (80nm) / α-NPD (30nm) / [One of Compound a + Fluorescent Green Dopant Compounds 202 ~ 249 (3%)] (30nm) / Alq3 (30nm) / LiF (0.5nm) / An organic light emitting diode having a structure of Al (60 nm) was prepared. These are referred to as samples 113 to 160, respectively.

평가예 2: 비교샘플 1,2 및 샘플 113~160의 발광 특성 평가Evaluation Example 2 Evaluation of Luminescence Characteristics of Comparative Samples 1,2 and 113-160

비교샘플 1,2 및 샘플 113~160에 대하여, Keithley sourcemeter “2400”, KONIKA MINOLTA “CS-2000”을 이용하여 발광휘도, 발광효율, 발광피크를 각각 평가하여, 그 결과를 하기 [제2표군]에 나타내었다. 상기 샘플들은 516~524nm 범위에서 녹색 발광 피크값을 보여주었다.For Comparative Samples 1 and 2 and Samples 113 to 160, the luminous intensity, luminous efficiency, and luminous peak were evaluated using Keithley sourcemeter “2400” and KONIKA MINOLTA “CS-2000”, respectively. ]. The samples showed green emission peaks in the range of 516-524 nm.

[제2표군][Second Marking Group]

Figure pat00135

Figure pat00135

Figure pat00136

Figure pat00136

상기 [제2표군]에 보여지는 바와 같이 샘플 113 내지 160은 비교샘플 1,2 에 비하여 향상된 발광 특성을 나타내었다.
As shown in [Second Table], samples 113 to 160 exhibited improved luminescence properties compared to Comparative Samples 1,2.

실시예 161~249Examples 161-249

상기 비교예 1 중, 전자수송층 화합물로서 화합물 d(Alq3) 대신 상기 합성예에 개시된 화학식 110~198으로 표시되는 화합물 110~198을 전자수송층 화합물로 각각 이용한 것을 제외하고는 상기 비교예 1과 동일한 방법으로 ITO/2-TNATA(80nm)/α-NPD(30nm)/ 화합물a+화합물c(30nm)/전자수송층화합물 110~198중 하나/LiF(0.5nm)/Al(60nm)의 구조를 갖는 유기발광소자를 제조하였다. 이를 각각 샘플 161 내지 249라고 한다.
In Comparative Example 1, the same method as in Comparative Example 1, except that Compound 110 to 198 represented by Formula 110 to 198 disclosed in Synthesis Example were used as the electron transporting layer compound instead of Compound d (Alq3) as the electron transporting layer compound. ITO / 2-TNATA (80nm) / α-NPD (30nm) / Compound a + Compound c (30nm) / Electron Transport Layer Compound 110 ~ 198 / LiF (0.5nm) / Al (60nm) The device was manufactured. These are referred to as samples 161 to 249, respectively.

평가예 3: 비교샘플 1 및 샘플 161~249의 발광 특성 평가Evaluation Example 3 Evaluation of Luminescence Characteristics of Comparative Sample 1 and Samples 161 to 249

비교샘플 1 및 샘플 161~249에 대하여, Keithley sourcemeter “2400”, KONIKA MINOLTA “CS-2000”을 이용하여 발광휘도, 발광효율, 발광피크를 각각 평가하여, 그 결과를 하기 [제3표군]에 나타내었다. 상기 샘플들은 513~520nm 범위에서 녹색 발광피크값을 보여주었다.For Comparative Sample 1 and Samples 161 to 249, the luminous intensity, luminous efficiency, and luminous peak were evaluated using Keithley sourcemeter “2400” and KONIKA MINOLTA “CS-2000”, and the results are shown in [Table 3] below. Indicated. The samples showed green emission peaks in the range of 513-520 nm.

[제3표군][Third Table]

Figure pat00137

Figure pat00137

Figure pat00138

Figure pat00138

Figure pat00139

Figure pat00139

상기 [제3표군] 에 보여지는 바와 같이 샘플 161 내지 249는 비교샘플 1 에 비하여 향상된 발광 특성을 나타내었다..As shown in [Table 3], Samples 161 to 249 showed improved luminescence properties compared to Comparative Sample 1.

Claims (8)

하기 화학식F로 표시되는 디벤조테트라센계 유도체:
[화학식F]
Figure pat00140



상기 식에서,
R1 내지 R3는 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기 이거나;
C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기이거나;
C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된
Figure pat00141
,
Figure pat00142
,
Figure pat00143
,
Figure pat00144
,
Figure pat00145
,
Figure pat00146
,
Figure pat00147
,
Figure pat00148
및
Figure pat00149
이거나; 또는
Figure pat00150
이며;
A 및 B는 각각 독립적으로 C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기 이거나;
C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기 이거나;
C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된
Figure pat00151
,
Figure pat00152
,
Figure pat00153
,
Figure pat00154
,
Figure pat00155
,
Figure pat00156
,
Figure pat00157
,
Figure pat00158
및
Figure pat00159
이거나;
C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 및 디히드로인돌기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이거나;
C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된
Figure pat00160
,
Figure pat00161
,
Figure pat00162
,
Figure pat00163
,
Figure pat00164
,
Figure pat00165
,
Figure pat00166
,
Figure pat00167
및
Figure pat00168
로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이거나;
Figure pat00169
이며;
상기 Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로,
C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기 이거나;
C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된
Figure pat00170
,
Figure pat00171
,
Figure pat00172
,
Figure pat00173
,
Figure pat00174
,
Figure pat00175
,
Figure pat00176
,
Figure pat00177
및
Figure pat00178
이며;
상기 Ar1 및 Ar2, 및 Ar3 및 Ar4는 각각 독립적으로 서로 결합하여 하나 이상의 C1~C5의 알킬기로 치환 또는 비치환된 5원환 내지 8원환의 고리를 형성할 수 있으며;
상기 R4, R5, R6, R7, R8 및 R9은 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기이며;
상기 X1, X2, X3, X4는 각각 독립적으로 탄소원자, 질소원자 또는 황원자이며;
상기 Y1, Y2, Y3, Y4는 각각 독립적으로 탄소원자, 질소원자 또는 황원자이다.Dibenzotetracene derivative represented by the following formula (F):
Formula F]
Figure pat00140



In this formula,
R 1 to R 3 are each independently a hydrogen atom, C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , or a Si (C 6 H 5 ) 3 group;
C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , Triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;
C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups
Figure pat00141
,
Figure pat00142
,
Figure pat00143
,
Figure pat00144
,
Figure pat00145
,
Figure pat00146
,
Figure pat00147
,
Figure pat00148
And
Figure pat00149
; or
Figure pat00150
;
A and B are each independently C 1 -C 10 straight or branched chain alkyl, C 1 -C 10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Or a Si (C 6 H 5 ) 3 group;
C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , Triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;
C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups
Figure pat00151
,
Figure pat00152
,
Figure pat00153
,
Figure pat00154
,
Figure pat00155
,
Figure pat00156
,
Figure pat00157
,
Figure pat00158
And
Figure pat00159
;
C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , 30-30 aryl substituted with one or more substituents selected from the group consisting of triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, and dihydroindole group Or a heteroaryl group of 5 to 60;
C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups
Figure pat00160
,
Figure pat00161
,
Figure pat00162
,
Figure pat00163
,
Figure pat00164
,
Figure pat00165
,
Figure pat00166
,
Figure pat00167
And
Figure pat00168
6 to 30 aryl groups or 5 to 60 heteroaryl groups substituted with one or more substituents selected from the group consisting of;
Figure pat00169
;
Ar1, Ar2, Ar3 and Ar4 are each independently,
C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups , Benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole , Triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;
C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl and pyrimidinyl groups
Figure pat00170
,
Figure pat00171
,
Figure pat00172
,
Figure pat00173
,
Figure pat00174
,
Figure pat00175
,
Figure pat00176
,
Figure pat00177
And
Figure pat00178
;
Ar 1 and Ar 2, and Ar 3 and Ar 4 may be each independently bonded to each other to form a 5- to 8-membered ring unsubstituted or substituted with one or more C 1 to C 5 alkyl groups;
R4, R5, R6, R7, R8 and R9 are each independently a hydrogen atom, C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, Nitrile, CF 3 , Si (CH 3 ) 3 , or Si (C 6 H 5 ) 3 groups;
X 1, X 2, X 3 and X 4 are each independently a carbon atom, a nitrogen atom or a sulfur atom;
Y1, Y2, Y3, and Y4 are each independently a carbon atom, a nitrogen atom, or a sulfur atom. 청구항 1에 있어서,
상기 6~30의 아릴기 또는 5~60의 헤테로아릴기는
페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 디히드로인돌기,
Figure pat00179
,
Figure pat00180
,
Figure pat00181
,
Figure pat00182
,
Figure pat00183
,
Figure pat00184
,
Figure pat00185
,
Figure pat00186
및
Figure pat00187
로 이루어진 군으로부터 선택되며;
상기 R4, R5, R6, R7, R8 및 R9은 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 직쇄 또는 분지쇄 알콕시, 할로겐, 히드록시, 티올, 니트로, 아민, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기이며;
상기 X1, X2, X3, X4는 각각 독립적으로 탄소원자, 질소원자 또는 황원자이며;
상기 Y1, Y2, Y3, Y4는 각각 독립적으로 탄소원자, 질소원자 또는 황원자인 것을 특징으로 하는 디벤조테트라센계 유도체.The method according to claim 1,
The aryl group of 6 to 30 or the heteroaryl group of 5 to 60
Phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, benzopyrenyl, perylene, fluorenyl, benzofluorenyl, fluoranthene, 9,9'-spirobi Fluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, Dehydroindole,
Figure pat00179
,
Figure pat00180
,
Figure pat00181
,
Figure pat00182
,
Figure pat00183
,
Figure pat00184
,
Figure pat00185
,
Figure pat00186
And
Figure pat00187
≪ / RTI >
R4, R5, R6, R7, R8 and R9 are each independently a hydrogen atom, C1-C10 straight or branched chain alkyl, C1-C10 straight or branched chain alkoxy, halogen, hydroxy, thiol, nitro, amine, Nitrile, CF 3 , Si (CH 3 ) 3 , or Si (C 6 H 5 ) 3 groups;
X 1, X 2, X 3 and X 4 are each independently a carbon atom, a nitrogen atom or a sulfur atom;
Y 1, Y 2, Y 3, and Y 4 are each independently a carbon atom, a nitrogen atom, or a sulfur atom. 청구항 2에 있어서,
R1 내지 R3는 각각 독립적으로 수소원자, C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 또는 피리미디닐이거나;
Figure pat00188
이며;
A 및 B는 각각 독립적으로 C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, 또는 Si(C6H5)3기 이거나;
C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 바이페닐, 나프틸, 터페닐, 페난트레닐, 벤조페난트레닐, 피레닐, 벤조피레닐, 페릴렌, 플루오레닐, 벤조플루오레닐, 플루오란텐, 9,9’-스피로바이플루오렌, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤조티아졸, 카르바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 또는 디히드로인돌기 이거나;
C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 직쇄 또는 분지쇄 알콕시, 할로겐, 니트릴, CF3, Si(CH3)3, Si(C6H5)3, 페닐, 나프틸, 피리디닐 및 피리미디닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된
Figure pat00189
,
Figure pat00190
,
Figure pat00191
,
Figure pat00192
,
Figure pat00193
,
Figure pat00194
,
Figure pat00195
,
Figure pat00196
및
Figure pat00197
이며;
상기 Ar1 및 Ar2, 및 Ar3 및 Ar4는 각각 독립적으로 서로 결합하여 하나 이상의 C1~C3의 알킬기로 치환 또는 비치환된 5원환 내지 6원환의 고리를 형성할 수 있으며;
상기 R4, R5, R6, R7, R8 및 R9은 각각 독립적으로 수소원자, C1~C5의 직쇄 또는 분지쇄 알킬, 또는 C1~C5의 직쇄 또는 분지쇄 알콕시기이며;
상기 X1, X2, X3, X4는 각각 독립적으로 탄소원자 또는 질소원자이며;
상기 Y1, Y2, Y3, Y4는 각각 독립적으로 탄소원자 또는 질소원자인 것을 특징으로 하는 디벤조테트라센계 유도체.The method according to claim 2,
R 1 to R 3 are each independently a hydrogen atom, C 1 -C 5 straight or branched chain alkyl, C 1 -C 5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl or pyrimidinyl;
Figure pat00188
;
A and B are each independently C 1 -C 5 straight or branched alkyl, C 1 -C 5 straight or branched alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , or Si (C 6 H 5 ) 3 Or;
C1-C5 straight or branched chain alkyl, C1-C5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl And phenyl, biphenyl, naphthyl, terphenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, benzopyrenyl, perylene, flu unsubstituted or substituted with one or more substituents selected from the group consisting of pyrimidinyl groups. Orenyl, benzofluorenyl, fluoranthene, 9,9'-spirobifluorene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzothiazole, carr A bazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, or dihydroindole group;
C1-C5 straight or branched chain alkyl, C1-C5 straight or branched chain alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ) 3 , phenyl, naphthyl, pyridinyl And pyrimidinyl group substituted or unsubstituted with one or more substituents selected from the group consisting of
Figure pat00189
,
Figure pat00190
,
Figure pat00191
,
Figure pat00192
,
Figure pat00193
,
Figure pat00194
,
Figure pat00195
,
Figure pat00196
And
Figure pat00197
;
Ar 1 and Ar 2, and Ar 3 and Ar 4 may be each independently bonded to each other to form a 5- to 6-membered ring unsubstituted or substituted with one or more C 1 to C 3 alkyl groups;
R 4, R 5, R 6, R 7, R 8 and R 9 are each independently a hydrogen atom, C 1 -C 5 straight or branched chain alkyl, or C 1 -C 5 linear or branched alkoxy group;
X 1, X 2, X 3 and X 4 are each independently a carbon atom or a nitrogen atom;
Y 1, Y 2, Y 3 and Y 4 are each independently a dibenzotetracene derivative, characterized in that the carbon atom or nitrogen atom. 청구항 3에 있어서,
상기 디벤조테트라센계 유도체는 하기 화합물 1 내지 화합물 249 중의 어느 하나 인 것을 특징으로 하는 디벤조테트라센계 유도체:


Figure pat00198




Figure pat00200

Figure pat00201



Figure pat00202



Figure pat00203

Figure pat00204

Figure pat00205

Figure pat00206

Figure pat00207



Figure pat00208



Figure pat00209

Figure pat00210

Figure pat00211



Figure pat00212

Figure pat00213
The method according to claim 3,
The dibenzotetracene-based derivative is any one of the following compounds 1 to 249 dibenzotethracene-based derivatives:


Figure pat00198




Figure pat00200

Figure pat00201



Figure pat00202



Figure pat00203

Figure pat00204

Figure pat00205

Figure pat00206

Figure pat00207



Figure pat00208



Figure pat00209

Figure pat00210

Figure pat00211



Figure pat00212

Figure pat00213
 음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기 전기발광 소자에 있어서,
상기 유기 박막층 중 적어도 1층 이상이 청구항 1의 디벤조테트라센계 유도체를 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기 전기발광 소자.In the organic electroluminescent element in which the organic thin film layer which consists of one layer or multiple layers containing a light emitting layer at least is clamped between a cathode and an anode,
At least one layer of the organic thin film layer contains the dibenzotetracene-based derivative of claim 1 alone or in combination of two or more. 청구항 5에 있어서,
상기 디벤조테트라센계 유도체가 상기 유기 박막층 중 발광층에 발광층 형광 녹색 호스트 화합물 또는 발광층 형광 녹색 도판트 화합물로 함유되어 있는 것을 특징으로 하는 유기 전기발광 소자.The method according to claim 5,
The dibenzotetracene-based derivative is an organic electroluminescent device, characterized in that the light emitting layer of the organic thin film layer contains a light emitting layer fluorescent green host compound or a light emitting layer fluorescent green dopant compound. 청구항 5에 있어서,
상기 유기 박막층이 전자수송층을 포함하며,
상기 디벤조테트라센계 유도체가 상기 전자수송층에 전자수송층 화합물로 함유되어 있는 것을 특징으로 하는 유기 전기발광 소자.The method according to claim 5,
The organic thin film layer includes an electron transport layer,
The dibenzotetracene-based derivative is an organic electroluminescent device, characterized in that contained in the electron transport layer as an electron transport layer compound. 청구항 6 또는 청구항 7에 있어서,
상기 유기 전기발광 소자가
양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 갖는 것을 특징으로 하는 유기 전기발광 소자.The method according to claim 6 or 7,
The organic electroluminescent device
An organic electroluminescent device comprising a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked in this order.
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