KR20140055925A - New organic electroluminescent compounds and organic electrolumescent device comprising the same - Google Patents

New organic electroluminescent compounds and organic electrolumescent device comprising the same

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KR20140055925A
KR20140055925A KR1020130024181A KR20130024181A KR20140055925A KR 20140055925 A KR20140055925 A KR 20140055925A KR 1020130024181 A KR1020130024181 A KR 1020130024181A KR 20130024181 A KR20130024181 A KR 20130024181A KR 20140055925 A KR20140055925 A KR 20140055925A
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compound
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fab
nmr
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KR101569101B1 (en
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김복영
안중복
강지승
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(주)씨에스엘쏠라
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Provided in the present invention are an organic luminescent compound which is a material for an organic electroluminescent device, and organic electroluminescent device including the same. [Chemical formula 1] [Chemical formula 2] The organic luminescent compound can be applied to an organic electroluminescent device as a light-emitting layer fluorescent blue dopant material, and in the case, the luminous efficiency and lifetime of the organic electroluminescent device can be improved.

Description

신규한 유기발광화합물 및 이를 포함하는 유기전기발광소자{NEW ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMESCENT DEVICE COMPRISING THE SAME}TECHNICAL FIELD [0001] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same. BACKGROUND ART < RTI ID = 0.0 >

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

표시 소자 중, 전기 발광 소자(electroluminescence device: EL device)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있으며, 1987년 이스트만 코닥(Eastman Kodak)사에서는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast and fast response speed. In 1987, Eastman Kodak Co., An organic EL device using an aromatic diamine and an aluminum complex having a low molecular weight as a material for forming a light emitting layer has been developed for the first time [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 factors for determining the performance such as luminous efficiency and lifetime in an organic EL device are the luminescent material. Some characteristics required for such a luminescent material are that the fluorescent quantum yield in a solid state must be large, and the mobility of electrons and holes And should not be easily decomposed during vacuum deposition, should form a uniform thin film, and be stable.

유기 발광 재료는 크게 고분자 재료와 저분자 재료로 나눌 수 있는데, 저분자 계열의 재료는 분자 구조 면에서 금속 착화합물과 금속을 포함하지 않는 순수 유기 발광 재료가 있다. 이러한 발광 재료로는 트리스(8-퀴놀리놀라토)알루미늄 착제 등의 킬레이트 착제, 쿠마린 유도체, 테트라페닐부타디엔 유도체, 비스스타이릴아릴렌 유도체, 옥사다이아졸 유도체 등의 발광 재료가 알려져 있고, 이들로부터는 청색에서 적색까지의 가시 영역 발광을 얻을 수 있다고 보고되었고 컬러 표시 소자의 실현이 기대되고 있다.Organic light emitting materials can be roughly divided into polymer materials and low molecular materials. In the molecular structure, there are pure organic light emitting materials which do not contain metal complex compounds and metals. 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 연구 개발이 시급한 부분이라고 하겠다.
On the other hand, in the case of blue materials, many materials have been developed and commercialized since the DPVBi of Idemitsu-Gosan, and the blue material system of Idemitsu-Gosan, the dinaphthylanthracen, the tetra (t-butyl) (Tetra (t-butyl) perylene) system have been known, but many research and development efforts are still required. The distill compound system of Idemitsu-Gosan, which is known to be the most efficient to date, has a power efficiency of 6 lm / W and a device lifetime of 30,000 hours or more. However, the degradation of color purity Resulting in only a few thousand hours of life when applied to a full color display. The blue light emission is advantageous in light emission efficiency even if the emission wavelength shifts a little toward the long wavelength side, but it can not satisfy the purple light color and is not easy to apply to a high quality display, and there is a problem in color purity, efficiency and thermal stability, It is an urgent part.

본 발명자들은 종래의 문제점을 해결하기 위하여 노력한 결과, 발광효율이 뛰어나고 수명이 획기적으로 개선된 유기전기발광소자를 실현하기 위한 새로운 유기발광화합물을 발견하게 되었다. As a result of efforts to solve the problems of the prior art, the present inventors have found a novel organic luminescent compound for realizing an organic electroluminescent device having excellent luminous efficiency and remarkably improved lifetime.

그러므로, 본 발명의 목적은 기존의 도판트 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기발광화합물 및 이를 발광재료로서 채용하는 고효율 및 장수명의 유기전기발광소자를 제공하는 것이다.
Therefore, an object of the present invention is to provide an organic electroluminescent compound having an excellent skeleton having a suitable color coordinate and a luminescent efficiency and a device life as compared with conventional dopant materials, and to provide a highly efficient and long-lived organic electroluminescent device .

본 발명은 하기 화학식 1 또는 화학식 2로 표시되는 유기발광화합물을 제공한다:The present invention provides an organic luminescent compound represented by the following formula (1) or (2): < EMI ID =

[화학식1][Chemical Formula 1]

Figure pat00001

Figure pat00001

[화학식2](2)

Figure pat00002
Figure pat00002

상기 화학식 1 및 2에서,In the above Formulas 1 and 2,

R1, R2, R3 및 R4는 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, 할로겐, 니트릴, CF3,Si(CH3)3,또는 Si(C6H5)3기 이거나,R1, R2, R3 and R4 are each independently a hydrogen atom, a linear or branched alkyl, halogen, nitrile of C1 ~ C10, CF 3, Si (CH 3) 3, or Si (C 6 H 5) or 03,

수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, 할로겐, 니트릴, CF3,Si(CH3)3및 Si(C6H5)3기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 나프틸, 페난트레닐, 플루오레닐, 피레닐, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤즈옥사졸, 벤조티아졸, 카바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌 또는 디히드로인돌이며; A hydrogen atom, a linear or branched alkyl, halogen, nitrile of C1 ~ C10, CF 3, Si (CH 3) 3 and Si (C 6 H 5) with one or more substituents selected from the group consisting of 3-group-substituted or unsubstituted Wherein R is selected from the group consisting of phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, Dibenzofurane, dibenzothiophene, benzimidazole, quinoline, indole or dihydroindole;

X, Y 및 Z은 각각 독립적으로 부존재 또는 C1~C10의 직쇄 또는 분지쇄 알킬기로 치환 또는 비치환된 메틸렌기이고, 부존재가 아닌 경우 Ar1, Ar2 또는 Ar3와 6~8원환을 형성하며;X, Y and Z each independently represent a methylene group which is unsubstituted or substituted or unsubstituted with a linear or branched alkyl group having 1 to 10 carbon atoms, and forms a 6- to 8-membered ring with Ar1, Ar2 or Ar3 when it is not present;

W는 부존재, 단순결합, O, S, 하나 이상의 메틸 또는 페닐기로 치환된 메틸렌, 또는 카보닐기이고, 부존재가 아닌 경우 Ar1 및 Ar4와 5~8원환을 형성하며; W is absent, a simple bond, O, S, a methylene or carbonyl group substituted with at least one methyl or phenyl group, and when not present, forms a 5- to 8-membered ring with Ar1 and Ar4;

Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로 중소소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3,Si(CH3)3,Si(C6H5)3,C(C6H5)3,페닐, 중수소로 치환된 페닐, 나프틸기로 치환된 페닐, 하나 이상의 페닐기로 치환된 페닐, 나프틸, 피리디닐, 피리미디닐, 벤즈옥사졸, 벤조티아졸 및 9,9-디메틸플루오레닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이다.Ar1, Ar2, Ar3 and Ar4 each independently represent a small wish Here, linear or branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10 of C1 ~ C10, CF 3, Si (CH 3) 3, Si (C 6 H 5 ) 3 , C (C 6 H 5 ) 3 , phenyl, phenyl substituted with deuterium, phenyl substituted with a naphthyl group, phenyl substituted with one or more phenyl groups, naphthyl, pyridinyl, pyrimidinyl, benzoxazole, A 6 to 30 aryl group or a 5 to 60 heteroaryl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of benzothiazole and 9,9-dimethylfluorenyl group.

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

음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기전기발광소자에 있어서, An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

상기 유기 박막층 중 적어도 1층이 본 발명의 유기발광화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전기발광소자를 제공한다.
At least one of the organic thin film layers contains the organic electroluminescent compound of the present invention singly or in combination of two or more.

본 발명에 따른 유기발광화합물은 발광효율 및 소자수명이 우수하며, 적절한 색좌표를 갖는다. The organic luminescent compound according to the present invention has excellent luminous efficiency and device life, and has an appropriate color coordinate.

또한, 본 발명의 유기발광화합물을 사용하여 제조되는 유기전기발광 소자는 고효율 및 장수명 특성을 갖는다.
In addition, the organic electroluminescent device manufactured using the organic electroluminescent compound of the present invention has high efficiency and long life.

본 발명은 하기 화학식 1 또는 화학식 2로 표시되는 유기발광화합물에 관한 것이다:The present invention relates to an organic luminescent compound represented by the following general formula (1) or (2)

[화학식1][Chemical Formula 1]

Figure pat00003

Figure pat00003

[화학식2](2)

Figure pat00004
Figure pat00004

상기 화학식 1 및 2에서,In the above Formulas 1 and 2,

R1, R2, R3 및 R4는 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, 할로겐, 니트릴, CF3,Si(CH3)3,또는 Si(C6H5)3기 이거나,R1, R2, R3 and R4 are each independently a hydrogen atom, a linear or branched alkyl, halogen, nitrile of C1 ~ C10, CF 3, Si (CH 3) 3, or Si (C 6 H 5) or 03,

수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, 할로겐, 니트릴, CF3,Si(CH3)3및 Si(C6H5)3기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 나프틸, 페난트레닐, 플루오레닐, 피레닐, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤즈옥사졸, 벤조티아졸, 카바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌 또는 디히드로인돌이며; A hydrogen atom, a linear or branched alkyl, halogen, nitrile of C1 ~ C10, CF 3, Si (CH 3) 3 and Si (C 6 H 5) with one or more substituents selected from the group consisting of 3-group-substituted or unsubstituted Wherein R is selected from the group consisting of phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, Dibenzofurane, dibenzothiophene, benzimidazole, quinoline, indole or dihydroindole;

X, Y 및 Z은 각각 독립적으로 부존재 또는 C1~C10의 직쇄 또는 분지쇄 알킬기로 치환 또는 비치환된 메틸렌기이고, 부존재가 아닌 경우 Ar1, Ar2 또는 Ar3와 6~8원환을 형성하며;X, Y and Z each independently represent a methylene group which is unsubstituted or substituted or unsubstituted with a linear or branched alkyl group having 1 to 10 carbon atoms, and forms a 6- to 8-membered ring with Ar1, Ar2 or Ar3 when it is not present;

W는 부존재, 단순결합, O, S, 하나 이상의 메틸 또는 페닐기로 치환된 메틸렌, 또는 카보닐기이고, 부존재가 아닌 경우 Ar1 및 Ar4와 5~8원환을 형성하며; W is absent, a simple bond, O, S, a methylene or carbonyl group substituted with at least one methyl or phenyl group, and when not present, forms a 5- to 8-membered ring with Ar1 and Ar4;

Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로 중소소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3,Si(CH3)3,Si(C6H5)3,C(C6H5)3,페닐, 중수소로 치환된 페닐, 나프틸기로 치환된 페닐, 하나 이상의 페닐기로 치환된 페닐, 나프틸, 피리디닐, 피리미디닐, 벤즈옥사졸, 벤조티아졸 및 9,9-디메틸플루오레닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이다. Ar1, Ar2, Ar3 and Ar4 each independently represent a small wish Here, linear or branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10 of C1 ~ C10, CF 3, Si (CH 3) 3, Si (C 6 H 5 ) 3 , C (C 6 H 5 ) 3 , phenyl, phenyl substituted with deuterium, phenyl substituted with a naphthyl group, phenyl substituted with one or more phenyl groups, naphthyl, pyridinyl, pyrimidinyl, benzoxazole, A 6 to 30 aryl group or a 5 to 60 heteroaryl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of benzothiazole and 9,9-dimethylfluorenyl group.

상기 6~30의 아릴기 또는 5~60의 헤테로아릴기는 페닐, 나프틸, 페난트레닐, 플루오레닐, 9,9-디메틸플루오레닐, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤즈옥사졸, 벤조티아졸, 카바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 디히드로인돌, 피레닐,

Figure pat00005
,
Figure pat00006
,
Figure pat00007
및 로 이루어진 군으로부터 선택될 수 있다. Wherein the 6 to 30 aryl group or the 5 to 60 heteroaryl group is selected from the group consisting of phenyl, naphthyl, phenanthrenyl, fluorenyl, 9,9-dimethylfluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, , Triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, dihydroindole, pyrenyl,
Figure pat00005
,
Figure pat00006
,
Figure pat00007
And ≪ / RTI >

상기에서 더욱 바람직하게는More preferably,

R1, R2, R3 및 R4는 수소원자 또는 메틸기이며; R1, R2, R3 and R4 are a hydrogen atom or a methyl group;

X, Y 및 Z은 각각 독립적으로 부존재 또는 2개의 메틸기로 치환된 메틸렌기이고, 부존재가 아닌 경우 Ar1, Ar2 또는 Ar3와 6원환을 형성하며;X, Y and Z each independently represent a methylene group which is unsubstituted or substituted with two methyl groups, and when not present, forms a 6-membered ring with Ar1, Ar2 or Ar3;

W는 부존재, 단순결합, O, S, 하나 이상의 메틸 또는 페닐기로 치환된 메틸렌, 또는 카보닐기이고, 부존재가 아닌 경우 Ar1 및 Ar4와 5~6원환을 형성하며; W is absent, a simple bond, O, S, methylene substituted with one or more methyl or phenyl groups, or a carbonyl group, and when not present, forms a 5- to 6-membered ring with Ar1 and Ar4;

Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로 중소소원자, C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 알콕시, 할로겐, 니트릴, CF3,Si(CH3)3,Si(C6H5)3,C(C6H5)3,페닐, 중수소로 치환된 페닐, 나프틸기로 치환된 페닐, 2개의 페닐기로 치환된 페닐, 나프틸, 벤즈옥사졸, 벤조티아졸기 및 9,9-디메틸플루오레닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 나프틸, 플루오레닐, 9,9-디메틸플루오레닐, 피리디닐, 피리미디닐, 벤즈옥사졸, 벤조티아졸, 카바졸, 디벤조퓨란, 디벤조티오펜, 피레닐,

Figure pat00009
,
Figure pat00010
,
Figure pat00011
및
Figure pat00012
로 이루어진 군으로부터 선택될 수 있다. C 1 -C 5 alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ), and the like, wherein Ar 1, Ar 2, Ar 3 and Ar 4 are each independently selected from the group consisting of a hydrogen atom, 5 ) 3 , C (C 6 H 5 ) 3 , phenyl, phenyl substituted with deuterium, phenyl substituted with naphthyl, phenyl substituted with two phenyl, naphthyl, benzoxazole, benzothiazole, -Dimethylfluorenyl group, phenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, pyridinyl, pyrimidinyl, benzoxazole, benzo Thiazole, carbazole, dibenzofuran, dibenzothiophene, pyrenyl,
Figure pat00009
,
Figure pat00010
,
Figure pat00011
And
Figure pat00012
≪ / RTI >

본 발명의 유기발광화합물은 유기 전기발광 소자용 재료로서 유용하게 사용될 수 있으며, 특히, 유기 전기발광 소자용 재료 중 발광층 형광 청색 도판트 화합물로서 유용하게 사용될 수 있다. The organic electroluminescent compound of the present invention can be usefully used as a material for an organic electroluminescent device, and in particular, can be usefully used as a fluorescent blue dopant compound in an emitting layer in an organic electroluminescent device material.

본 발명의 유기발광화합물은 하기 [제1표군(群)]에 나타낸 화학구조를 가질 수 있다.The organic luminescent compound of the present invention may have the chemical structure shown in the following [first group (s)].

[제1표군(群)] [First group (group)]

Figure pat00013
Figure pat00014
Figure pat00015
Figure pat00016
Figure pat00017
Figure pat00018
Figure pat00019
Figure pat00020
Figure pat00021
Figure pat00022
Figure pat00023
Figure pat00024
Figure pat00025
Figure pat00026
Figure pat00013
Figure pat00014
Figure pat00015
Figure pat00016
Figure pat00017
Figure pat00018
Figure pat00019
Figure pat00020
Figure pat00021
Figure pat00022
Figure pat00023
Figure pat00024
Figure pat00025
Figure pat00026

본 발명은 또한,The present invention also relates to

음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기전기발광소자에 있어서, An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

상기 유기 박막층 중 적어도 1층이 본 발명의 유기발광화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전기발광소자에 관한 것이다.Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of the present invention singly or in combination of two or more thereof.

상기 유기발광화합물은 상기 유기 박막층 중 발광층에 발광층 형광 청색 도판트 화합물로 함유되는 경우에 우수한 특성을 나타낸다.The organic luminescent compound exhibits excellent characteristics when the luminescent layer of the organic thin film layer contains the luminescent layer as a fluorescent blue dopant compound.

상기 유기전기발광소자는 The organic electroluminescent device

양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 가질 수 있다.An anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode stacked in this order.

이하에서, 본 발명의 유기전기발광소자에 대하여 예를 들어 설명한다. 그러나, 하기에 예시된 내용이 본 발명의 유기전기발광소자를 한정하는 것은 아니다.Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the following examples do not limit the organic electroluminescent device of the present invention.

본 발명의 유기전기발광소자는 양극(정공주입전극), 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 may have a structure in which a cathode (a hole injection electrode), a hole injection layer (HIL) and / or a hole transport layer (HTL), a light emitting layer (EML) Preferably, an electron blocking layer (EBL) may be additionally provided 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) have.

본 발명에 따른 유기전기발광소자의 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 electroluminescence device according to the present invention, a cathode material is coated on the surface of a substrate by a conventional method to form a cathode. 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 물질로는 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. As the hole transporting layer material, bis (N- (1-naphthyl-n-phenyl)) benzidine (? -NPD), N, N'- -Benzidine (NPB) or N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-diphenyl-4,4'-diamine (TPD).

상기 정공수송층 표면에 발광층(EML) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 발광층을 형성한다. 이때, 사용되는 발광층 물질 중 단독 발광물질 또는 발광 호스트 물질은 특별히 제한되지 않으며, 그 예로서 녹색의 경우 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3)가, 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 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. In this case, the single luminescent material or the luminescent host material is not particularly limited, and examples thereof include tris (8-hydroxyquinolinolato) aluminum (Alq3) for green, Balq (8- Hydroxyquinoline beryllium salts), DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl) series, Spiro material, Spiro- DPVBi Biphenyl), LiPBO (2- (2-benzoxazolyl) -phenol lithium salt), bis (diphenylvinyl) -4,4'- Benzene, aluminum-quinoline metal complexes, metal complexes of imidazole, thiazole and oxazole, and the like.

발광층 물질 중 발광 호스트와 함께 사용될 수 있는 도펀트(dopant)의 경우 본 발명의 유기발광화합물이 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.The organic luminescent compound of the present invention can be preferably used for a dopant that can be used together with a luminescent host among luminescent layer materials. IDE102, IDE105, phosphorescent dopants available from Idemitsu as additional fluorescent dopants include tris Iridium (III) (Ir (ppy) 3), iridium (III) bis [(4,6-difluorophenyl) pyridinate-N, C-2 '] picolinate Platinum (II) octaethylporphyrin (PtOEP), TBE002 (Cobion) and the like can be used as the starting material (see Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084).

상기 발광층 표면에 전자수송층(ETL) 물질을 통상적인 방법으로 진공 열증착 또는 스핀 코팅하여 전자수송층을 형성한다. 이때, 사용되는 전자수송층 물질의 경우 특별히 제한되지 않으며, 바람직하게는 트리스(8-하이드록시퀴놀리놀라토)알루미늄(Alq3)을 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 electron transporting material to be used is not particularly limited, and tris (8-hydroxyquinolinolato) aluminum (Alq3) can be preferably 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 a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode capable of transmitting light.

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 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, Electron injection layer / electron transporting layer / hole blocking layer / light emitting layer / hole transporting layer / hole injecting layer / anode.

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 of synthesizing the compounds of the present invention will be described with reference to representative examples. However, the method of synthesizing the compounds of the present invention is not limited to the following exemplified methods, and the compounds of the present invention can be produced by the methods exemplified below and by methods known in the art.

화합물 1의 합성Synthesis of Compound 1

[반응식 1][Reaction Scheme 1]

Figure pat00027
Figure pat00027

Figure pat00028
Figure pat00028

중간체 화합물 [1-1], [1-2] 및 [1-3]의 제조Preparation of intermediate compounds [1-1], [1-2] and [1-3]

3L 반응플라스크에 질소 분위기에서 5,9-디브로모-7,7-디메틸-7H-벤조[c]플로렌 200g(0.50mol), 2-아미노아세토페논 60.6mL(0.50mmol), 분말구리(copper powder) 15.8g(0.25mmol), 탄산칼륨 137.5g(0.99mol)에 디페닐에테르 1L를 넣고 180℃로 33시간 가열 교반하였다. 반응 종료 후 메탄올 1L를 가하여 교반하고 감압 여과하고, 다시 아세톤 2L와 증류수 6L를 가하여 교반한 뒤 감압 여과하였다. 고체를 실리카겔 크로마토 그라프로 분리 정제하여 밝은 노란색 고체의 중간체 화합물 [1-1] 54.5g(24%), [1-2] 61.3g(27%), [1-3] 15.2g(6%)을 수득하였다.(0.50 mol) of 5,9-dibromo-7,7-dimethyl-7H-benzo [c] fluorene, 60.6 mL (0.50 mmol) of 2-aminoacetophenone, and powdered copper 15.5 g (0.25 mmol) of copper powder and 137.5 g (0.99 mol) of potassium carbonate were added 1 L of diphenyl ether and the mixture was heated and stirred at 180 캜 for 33 hours. After completion of the reaction, 1 L of methanol was added, and the mixture was stirred, followed by filtration under reduced pressure. 2 L of acetone and 6 L of distilled water were further added thereto, followed by stirring and filtration under reduced pressure. The solid was separated and purified by silica gel chromatography to obtain 54.5 g (24%) of intermediate compound [1-1] as a light yellow solid, 61.3 g (27%) of [1-2], 15.2 g (6% ≪ / RTI >

중간체 화합물 [1-4]의 제조Preparation of intermediate compound [1-4]

3L 반응플라스크에 질소 분위기에서 화합물 [1-1] 54.5g(0.12mol)을 테트라히드로퓨란 1L에 녹이고, 실온에서 메틸마그네슘브로마이드(1.4 M in THF:toluene=1:3) 170.6mL(0.24mol)를 천천히 적가하였다. 13시간 동안 교반시킨 후 NH4Cl수용액 800mL를 가해 반응을 종료시키고, 에틸아세테이트로 추출하여 무수황산 마그네슘으로 건조하여 여과하고, 여과액은 감압 농축한 뒤, 실리카겔 크로마토그라프로 분리정제하여 밝은 노란색 고체의 중간체 화합물 [1-4] 38.4g (68%)을 수득하였다.In a 3 L reaction flask, 54.5 g (0.12 mol) of the compound [1-1] was dissolved in 1 L of tetrahydrofuran in a nitrogen atmosphere and 170.6 mL (0.24 mol) of methylmagnesium bromide (1.4 M in THF: toluene = 1: 3) Was slowly added dropwise. After stirring for 13 hours, 800 mL of NH 4 Cl aqueous solution was added to terminate the reaction. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and then purified by silica gel chromatography to obtain a light yellow solid 38.4 g (68%) of intermediate compound [1-4] was obtained.

중간체 화합물 [1-5], [1-6]의 제조Preparation of intermediate compounds [1-5], [1-6]

3L 반응플라스크에 질소 분위기에서 화합물 [1-4] 38.4g(0.081mol)을 톨루엔 1L에 녹이고 메탄설폰산 47.5mL(0.73mol)을 적가한다. 반응 종료 후 테트라하이드로퓨란과 메탄올을 각각 500mL씩 넣고 1시간 동안 교반시킨 후 에틸아세테이트로 추출하여 무수황산 마그네슘으로 건조하여 여과하고, 여과액은 감압 농축한 뒤, 실리카겔 크로마토그라프로 분리정제하여 밝은 노란색 고체의 중간체 화합물 [1-5] 11.8g(32%), [1-6] 10.0g(27%)를 수득하였다.In a 3 L reaction flask, 38.4 g (0.081 mol) of the compound [1-4] is dissolved in 1 L of toluene in a nitrogen atmosphere, and 47.5 mL (0.73 mol) of methanesulfonic acid is added dropwise. After completion of the reaction, 500 mL of tetrahydrofuran and methanol were added to each 500 mL of the mixture, and the mixture was stirred for 1 hour. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography, 11.8 g (32%) of solid intermediate compound [1-5] and 10.0 g (27%) of [1-6] were obtained.

중간체 화합물 [1-6]의 제조Preparation of intermediate compound [1-6]

500mL 반응플라스크에 질소 분위기에서 화합물 [1-5] 11.8g(25.97mmol), 요오드벤젠 15.9g(77.90mmol), 분말구리(copper powder) 0.83g(12.98mmol), 탄산칼륨 7.18g(51.94mmol)에 디페닐에테르 130mL를 넣고 180℃로 18시간 가열 교반하였다. 반응 종료 후 메탄올 150mL를 가하여 교반하고 감압 여과하고, 다시 아세톤 200mL와 증류수 600mL를 가하여 교반한 뒤 감압 여과하였다. 고체를 실리카겔 크로마토 그라프로 분리 정제하여 밝은 노란색 고체의 중간체 화합물 [1-7] 10.1g(73%)을 수득하였다.(25.97mmol) of compound [1-5], 15.9g (77.90mmol) of iodobenzene, 0.83g (12.98mmol) of copper powder and 7.18g (51.94mmol) of potassium carbonate were added to a 500ml reaction flask in a nitrogen atmosphere, , 130 mL of diphenyl ether was added and the mixture was heated and stirred at 180 ° C for 18 hours. After completion of the reaction, 150 mL of methanol was added, stirred, and filtered under reduced pressure. 200 mL of acetone and 600 mL of distilled water were further added thereto, followed by stirring, followed by filtration under reduced pressure. The solid was separated and purified by silica gel chromatography to obtain 10.1 g (73%) of a light yellow solid intermediate compound [1-7].

화합물 [1]의 제조 Preparation of compound [1]

100mL 반응플라스크에 화합물 [1-7] 1.0g(1.89mmol), 디페닐아민 0.41g(2.45mmol), 소듐터트부톡사이드 0.36g(3.77mmol), 팔라듐아세테이트 0.02g(0.10mmol), 트리터트부틸포스핀 0.04g(0.19mmol)에 톨루엔 20mL를 넣고 3시간 환류 교반하였다. 반응 종료 후 디클로로메탄으로 추출하여 무수황산 마그네슘으로 건조하여 여과하고, 여과액은 감압 농축한 뒤, 실리카겔 크로마토그라프로 분리정제하여 노란색 고체의 화합물 [1] 0.94g (81%)을 수득하였다.1.0 g (1.89 mmol) of the compound [1-7], 0.41 g (2.45 mmol) of diphenylamine, 0.36 g (3.77 mmol) of sodium tert.butoxide, 0.02 g (0.10 mmol) of palladium acetate, 20 mL of toluene was added to 0.04 g (0.19 mmol) of phosphine, and the mixture was refluxed and stirred for 3 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and then purified by silica gel chromatography to obtain 0.94 g (81%) of a yellow solid compound [1].

상기 반응식 1의 방법에 따라, 화합물 1내지 296의 화합물을 제조하였으며, 하기 [합성예]에 그 결과를 나타내었다.The compounds 1 to 296 were prepared according to the method of Reaction Scheme 1 above, 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 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 6H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 6H), 6.95 1H), 1.68 (s, 6H), 1.62 (s, 6H), 6.62 (s,

MS/FAB: 618(M+)MS / FAB: 618 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 6.95 6H), 1.62 (s, 6H), 1.62 (s, 6H), 6.69 (d, )

MS/FAB: 628(M+)MS / FAB: 628 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 7.95~6.88(m, 6H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45~6.37(m, 6H), 2.24(s, 6H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 7.95 6H), 1.68 (s, 6H), 1.62 (s, 6H), 6.87 (m, , 6H)

MS/FAB: 646(M+)MS / FAB: 646 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.91(m, 6H), 6.71(t, 1H), 6.63(m, 2H), 6.53(d, 2H), 6.45(d, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.25(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 6.95 2H), 6.53 (d, 2H), 6.45 (d, 5H), 6.37 (s, 1.62 (s, 6H), 1.25 (s, 18H)

MS/FAB: 731(M+)MS / FAB: 731 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.05(m, 6H), 6.95~6.91(m, 2H), 6.71(t, 1H), 6.63(m, 2H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 0.15(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.05 (m, 6H) , 6.95 (m, 2H), 6.71 (m, 2H), 6.71 (m, 2H) , 6H), 0.15 (s, 18H)

MS/FAB: 763(M+)MS / FAB: 763 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.89(m, 6H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 6.95 1H), 1.68 (s, 6H), 1.62 (s, 6H), 6.69 (s,

MS/FAB: 654(M+)MS / FAB: 654 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.29(m, 4H), 7.10(t, 2H), 6.95~6.89(m, 2H), 6.71~6.63(m, 7H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (d, IH), 7.98 (d, IH), 7.58 (s, IH), 7.42-7.40 (d, 2H), 6.95 (d, 2H), 6.95-6.89 (m, 2H), 6.71-6.63 ), 1.62 (s, 6H)

MS/FAB: 668(M+)MS / FAB: 668 (M < + >).

[합성예 8] 화합물 [8]의 합성[Synthesis Example 8] Synthesis of compound [8]

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98~7.92(m, 5H), 7.58(s, 1H), 7.47~7.40(m, 8H), 7.28(t, 2H), 7.10(t, 2H), 6.95~6.88(m, 4H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 ~ 7.92 (m, 5H), 7.58 (s, 1H), 7.47 ~ 7.40 (m, 8H), 7.28 (t, 2H) 2H), 6.95 (d, 1H), 6.37 (s, 1H), 1.68 (s, 2H) , ≪ / RTI > 6H), 1.62 (s, 6H)

MS/FAB: 718(M+)MS / FAB: 718 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.78~7.64(m, 8H), 7.58(s, 1H), 7.42~7.39(m, 6H), 7.26(t, 2H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.78 ~ 7.64 (m, 8H), 7.58 (s, 1H), 7.42 ~ 7.39 (m, 6H) , 7.26 (t, 2H), 7.10 (t, 2H), 6.95-6.92 (m, 2H), 6.71-6.63 , 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 718(M+)MS / FAB: 718 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.44~7.31(m, 16H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.53(m, 9H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.44 ~ 7.31 (m, 16H), 7.10 (t, 2H), 6.95 (S, 6H), 1.62 (s, 6H), 1.62 (s, 2H)

MS/FAB: 771(M+)MS / FAB: < / RTI & gt ; 771 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.77(d, 2H), 7.58(s, 1H), 7.52(d, 2H), 7.45~7.40(m, 4H), 7.28(t, 2H), 7.18~7.10(m, 4H), 6.95~6.89(m, 2H), 6.71~6.63(m, 5H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.77 (d, 2H), 7.58 (s, 1H), 7.52 (d, 2H), 7.45 ~ 7.40 (m, 4H), 7.28 (t, 2H), 7.18 ~ 7.10 (m, 4H), 6.95 ~ 6.89 (m, 2H), 6.71 ~ 6.63 (s, 1 H), 1.68 (s, 6 H), 1.62 (s, 18 H)

MS/FAB: 851(M+)MS / FAB: < / RTI & gt ; 851 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.77(d, 2H), 7.65~7.45(m, 11H), 7.28~7.06(m, 18H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.77 (d, 2H), 7.65 ~ 7.45 (m, 11H), 7.28 ~ 7.06 (m, 18H) (S, 6H), 1.62 (s, 6H), 1.62 (s, 6H), 6.75-6.92 (m, 2H), 6.71-6.63

MS/FAB: 1095(M+)MS / FAB: 1095 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.77(d, 3H), 7.58(s, 1H), 7.52~7.40(m, 6H), 7.28~6.92(m, 26H), 6.71~6.63(m, 4H), 6.53~6.45(m, 5H), 6.37~6.34(m, 3H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.77 (d, 3H), 7.58 (s, 1H), 7.52 ~ 7.40 (m, 6H), 7.28 6H), 1.62 (s, 6H), 1.62 (s, 6H), 6.62 (s,

MS/FAB: 1099(M+)MS / FAB: 1099 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.92(m, 6H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 5H), 6.37(s, 1H), 2.77(m, 2H), 1.68(s, 6H), 1.62(s, 6H), 1.10(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 6.95 2H), 1.68 (s, 6H), 6.71 (d, 2H), 6.71 (d, ), 1.62 (s, 6H), 1.10 (s, 12H)

MS/FAB: 702(M+)MS / FAB: 702 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.05(m, 4H), 6.91(t, 4H), 6.71~6.53(m, 7H), 6.45~6.37(m, 4H), 2.02(s, 6H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.05 (m, 4H) , 6.91 (t, 4H), 6.71-6.53 (m, 7H), 6.45-6.37 (m, 4H)

MS/FAB: 646(M+)MS / FAB: 646 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.63(m, 7H), 6.53(d, 2H), 6.45~6.37(m, 6H), 3.73(s, 6H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 6.95 6H), 1.68 (s, 6H), 1.62 (s, 2H), 6.73 (d, 2H) , 6H)

MS/FAB: 678(M+)MS / FAB: 678 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98~7.97(m, 3H), 7.58(s, 1H), 7.45~7.40(m, 4H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.45(m, 10H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 ~ 7.97 (m, 3H), 7.58 (s, 1H), 7.45 ~ 7.40 (m, 4H), 7.10 (t, 2H) (S, 6H), 1.62 (s, 6H), 1.62 (s, 6H)

MS/FAB: 620(M+)MS / FAB: 620 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 5H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.89(m, 6H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 5H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 6.95 6H), 1.62 (s, 6H), 6.68 (s, 2H), 6.68 (s, )

MS/FAB: 620(M+)MS / FAB: 620 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.99~7.94(m, 5H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.26(t, 2H), 7.17~7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.99 ~ 7.94 (m, 5H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.26 (t, 2H) , 7.17-7.10 (m, 4H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 3H), 6.53 (d, 2H), 6.45 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 620(M+)MS / FAB: 620 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.80(s, 2H), 8.40~8.36(m, 5H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.80 (s, 2H), 8.40 ~ 8.36 (m, 5H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H) 2H), 6.95 (d, IH), 6.37 (s, IH), 1.68 (m, 2H) , ≪ / RTI > 6H), 1.62 (s, 6H)

MS/FAB: 622(M+)MS / FAB: 622 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36~8.35(m, 5H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.83(m, 4H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 ~ 8.35 (m, 5H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H) , 6.95 (d, 1H), 6.37 (s, 1H), 1.68 (s, 6H), 1.62 (s, 2H) , 6H)

MS/FAB: 622(M+)MS / FAB: 622 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.65(s, 2H), 8.36(d, 1H), 7.98(d, 1H), 7.70(d, 2H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.30(m, 4H), 7.10~7.09(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.65 (s, 2H), 8.36 (d, 1H), 7.98 (d, 1H), 7.70 (d, 2H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.30 (m, 4H), 7.10-7.09 (m, 4H), 6.95-6.92 (m, 2H), 6.71-6.63 (s, 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 720(M+)MS / FAB: 720 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 8.18(t, 2H), 8.07(d, 2H), 7.98(d, 1H), 7.58(s, 1H), 7.47~7.31(m, 8H), 7.10(t, 2H), 6.95~6.89(m, 4H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 8.18 (t, 2H), 8.07 (d, 2H), 7.98 (d, 1H), 7.58 (s, 1H), 7.47 ~ 7.31 (d, 2H), 6.45 (d, IH), 6.37 (s, IH), 7.10 (m, 4H) ), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 720(M+)MS / FAB: 720 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.82~6.63(m, 9H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 6.95 6H), 1.62 (s, 6H), 6.62 (s, 2H), 6.82 (m, 2H), 6.82-6.63

MS/FAB: 632(M+)MS / FAB: 632 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.18~7.10(m, 6H), 6.95~6.92(m, 2H), 6.81(d, 2H), 6.71~6.62(m, 5H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.18 ~ 7.10 (m, 6H) 2H), 6.71 (d, 2H), 6.81 (d, 2H), 6.71-6.62 (m, 2H) , ≪ / RTI > 6H), 1.62 (s, 6H)

MS/FAB: 668(M+)MS / FAB: 668 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.27(d, 4H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.27 (d, 4H), 7.10 (m, 2H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 3H), 6.53-6.45 , 6H)

MS/FAB: 754(M+)MS / FAB: 754 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 3H), 7.98(d, 1H), 7.88(d, 2H), 7.71(d, 2H), 7.58(s, 1H), 7.42~7.40(m, 6H), 7.17~7.10(m, 4H), 6.95~6.92(m, 2H), 6.76~6.63(m, 5H), 6.53(d, 2H), 6.45(s, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 3H), 7.98 (d, 1H), 7.88 (d, 2H), 7.71 (d, 2H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 6H), 7.17-7.10 (m, 4H), 6.95-6.92 (m, 2H), 6.76-6.63 , 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 831(M+)MS / FAB: < / RTI & gt ; 831 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.79(d, 2H), 7.58~7.56(m, 3H), 7.42~7.40(m, 2H), 7.22~7.10(m, 8H), 6.97~6.92(m, 4H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 6.29(d, 2H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.79 (d, 2H), 7.58 ~ 7.56 (m, 3H), 7.42 ~ 7.40 (m, 2H) , 6.27 (d, 2H), 6.45 (d, 1H), 6.37 (s, 1H), 6.29 (d, 2H), 1.68 (s, 6H), 1.62 (s, 6H)

MS/FAB: 798(M+)MS / FAB: 798 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.11~7.06(m, 8H), 6.95~6.87(m, 4H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.11 ~ 7.06 (m, 8H) , 6.95 (d, 2H), 6.45 (d, 1H), 6.37 (s, 1H), 1.68 (s, 6H), 1.62 , 6H)

MS/FAB: 648(M+)MS / FAB: 648 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45~8.42(m, 2H), 8.02~7.99(m, 2H), 7.84(d, 1H), 7.58~7.53(m, 2H), 7.44~7.40(m, 4H), 7.23~7.10(m, 5H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 ~ 8.42 (m, 2H), 8.02 ~ 7.99 (m, 2H), 7.84 (d, 1H), 7.58 ~ 7.53 (m, 2H), 7.44 ~ 7.40 ( (d, 2H), 6.45 (d, 1H), 1.68 (s, 2H), 7.23-7.10 (m, 5H), 6.95-6.92 6H), 1.62 (s, 6H)

MS/FAB: 616(M+)MS / FAB: 616 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.92(m, 6H), 6.71~6.63(m, 5H), 6.53(d, 2H), 6.45(d, 3H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.58(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 6.95 6H), 1.68 (s, 6H), 1.62 (s, 6H), 6.71 (d, 2H) ), 1.58 (s, 6 H)

MS/FAB: 658(M+)MS / FAB: 658 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.23~6.91(m, 18H), 6.71~6.63(m, 7H), 6.45~6.37(m, 4H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.23 ~ 6.91 (m, 18H) , 6.71-6.63 (m, 7H), 6.45-6.37 (m, 4H), 1.68 (s, 6H)

MS/FAB: 783(M+)MS / FAB: 783 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.43~7.40(m, 4H), 7.29(t, 2H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.81(t, 2H), 6.71~6.63(m, 5H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.43 ~ 7.40 (m, 4H), 7.29 (t, 2H), 7.10 (t, 2H), 6.95-6.92 (m, 2H), 6.81 (t, 2H), 6.71-6.63 ), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 644(M+)MS / FAB: 644 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 6H), 6.53(d, 4H), 6.45~6.37(m, 4H), 3.73(s, 3H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 4H), 6.95 3H), 1.68 (s, 6H), 1.62 (s, 3H), 6.92 (m, 2H) , 6H)

MS/FAB: 648(M+)MS / FAB: 648 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53(m, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68~1.62(d, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (m, 4H), 6.95 2H), 6.71-6.63 (m, 4H), 6.53 (m, 4H), 6.45 (d,

MS/FAB: 624(M+)MS / FAB: 624 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(m, 4H), 6.95~6.88(m, 4H), 6.71~6.63(m, 4H), 6.53(m, 4H), 6.45~6.37(d, 4H), 2.24(s, 3H), 1.68~1.62(d, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (m, 4H), 6.95 2H), 1.68-1.62 (d, 12H), 6.88 (m, 4H), 6.71 (m,

MS/FAB: 633(M+)MS / FAB: 633 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(m, 4H), 6.95~6.91(m, 4H), 6.71~6.63(m, 4H), 6.53~6.37(m, 8H), 1.68~1.62(d, 12H), 1.25(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (m, 4H), 6.95 (M, 4H), 6.71-6.63 (m, 4H), 6.53-6.37 (m, 8H), 1.68-1.62

MS/FAB: 675(M+)MS / FAB: 675 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.05(m, 6H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53~6.37(m, 8H), 1.68~1.62(d, 12H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.05 (m, 6H) , 6.95-6.92 (m, 2H), 6.71-6.63 (m, 4H), 6.53-6.37 (m, 8H), 1.68-1.62

MS/FAB: 691(M+)MS / FAB: 691 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(m, 4H), 6.95~6.89(m, 4H), 6.71~6.63(m, 4H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.68~1.62(d, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (m, 4H), 6.95 (M, 4H), 6.71-6.63 (m, 4H), 6.53-6.45 (m, 7H), 6.37

MS/FAB: 637(M+)MS / FAB: 637 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.29(m, 2H), 7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 6H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68~1.62(d, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.29 (m, 2H), 7.10 6H), 6.53-6.45 (m, 5H), 6.37 (s, IH), 1.68-1.62 (m, 2H), 6.71-6.62

MS/FAB: 644(M+)MS / FAB: 644 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98~7.92(m, 3H), 7.58(s, 1H), 7.47~7.40(m, 5H), 7.28(t, 1H), 7.10(m, 4H), 6.95~6.88(m, 3H), 6.71~6.63(m, 4H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68~1.62(d, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 ~ 7.92 (m, 3H), 7.58 (s, 1H), 7.47 ~ 7.40 (m, 5H), 7.28 (t, 1H) (M, 4H), 7.10 (m, 4H), 6.95-6.88 (m, 3H), 6.71-6.63

MS/FAB: 669(M+)MS / FAB: 669 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.78~7.64(m, 4H), 7.58(s, 1H), 7.47~7.39(m, 4H), 7.26(t, 1H), 7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68~1.62(d, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.78 ~ 7.64 (m, 4H), 7.58 (s, 1H), 7.47 ~ 7.39 (m, 4H) , 7.26 (t, 1H), 7.10 (m, 4H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 4H), 6.53-6.45 ~ 1.62 (d, 12H)

MS/FAB: 669(M+)MS / FAB: 669 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.47~7.31(m, 9H), 7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.53(m, 10H), 6.45(d, 1H), 6.37(s, 1H), 1.68~1.62(d, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (d, IH), 7.98 (d, IH), 7.58 (s, IH), 7.47-7.31 2H), 6.71-6.53 (m, 10H), 6.45 (d, 1H), 6.37

MS/FAB: 695(M+)MS / FAB: 695 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.77(d, 1H), 7.58(s, 1H), 7.52(d, 1H), 7.45~7.40(m, 3H), 7.28(t, 1H), 7.18~7.10(m, 5H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68~1.62(m, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.77 (d, 1H), 7.58 (s, 1H), 7.52 (d, 1H), 7.45 ~ 7.40 (m, 3H), 7.28 (t, 1H), 7.18-7.10 (m, 5H), 6.95-6.92 (m, 2H), 6.71-6.63 (s, 1 H), 1.68-1.62 (m, 18 H)

MS/FAB: 735(M+)MS / FAB: 735 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.77(d, 1H), 7.65(d, 2H), 7.58(s, 1H), 7.52~7.25(m, 4H), 7.28~7.10(m, 12H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68~1.62(m, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.77 (d, 1H), 7.65 (d, 2H), 7.58 (s, 1H), 7.52 ~ 7.25 (m, 4H), 7.28-7.10 (m, 12H), 6.95-6.92 (m, 2H), 6.71-6.63 ~ 1.62 (m, 12H)

MS/FAB: 857(M+)MS / FAB: < / RTI & gt ; 857 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.77(d, 1H), 7.58(s, 1H), 7.52~7.25(m, 4H), 7.28~7.01(m, 18H), 6.71~6.63(m, 5H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68~1.62(m, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.77 (d, 1H), 7.58 (s, 1H), 7.52 ~ 7.25 (m, 4H), 7.28 1H), 6.71-6.63 (m, 5H), 6.53-6.45 (m, 6H), 6.37 (s,

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

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(m, 4H), 6.95~6.92(m, 4H), 6.71~6.63(m, 4H), 6.53~6.45(m, 7H), 6.37(s, 1H), 2.77(m, 1H), 1.68~1.62(m, 12H), 1.10(d, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (m, 4H), 6.95 2H), 1.68-1.62 (m, 12H), 1.10 (m, 4H), 6.71 (m, (d, 6H)

MS/FAB: 660(M+)MS / FAB: 660 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98~7.97(m, 2H), 7.58(s, 1H), 7.45~7.40(m, 3H), 7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.45(m, 11H), 6.37(s, 1H), 1.68~1.62(m, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 ~ 7.97 (m, 2H), 7.58 (s, 1H), 7.45 ~ 7.40 (m, 3H), 7.10 (m, 4H) 2H), 6.71-6.45 (m, 11H), 6.37 (s, 1H), 1.68-1.62 (m, 12H)

MS/FAB: 620(M+)MS / FAB: 620 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.80(s, 1H), 8.40~8.36(m, 3H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68~1.62(m, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.80 (s, 1H), 8.40 ~ 8.36 (m, 3H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H) 2H), 6.71-6.63 (m, 4H), 6.53-6.45 (m, 5H), 6.37 (s, 1H), 1.68-1.62 (m, 12H)

MS/FAB: 621(M+)MS / FAB: 621 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.18~7.10(m, 6H), 6.95~6.92(m, 2H), 6.81(d, 1H), 6.71~6.62(m, 5H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68~1.62(m, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.18 ~ 7.10 (m, 6H) 2H), 6.81 (d, 1H), 6.71-6.62 (m, 5H), 6.53-6.45 (m, 5H), 6.37

MS/FAB: 644(M+)MS / FAB: 644 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.27(d, 2H), 7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.68~1.62(m, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.27 (d, 2H), 7.10 (m, 2H), 6.71-6.63 (m, 4H), 6.53-6.45 (m, 7H), 6.37

MS/FAB: 687(M+)MS / FAB: 687 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36~8.35(m, 2H), 7.98(d, 1H), 7.88(d, 1H), 7.7(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 4H), 7.10(t, 4H), 6.96~6.92(m, 3H), 6.78~6.63(m, 5H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 ~ 8.35 (m, 2H), 7.98 (d, 1H), 7.88 (d, 1H), 7.7 (d, 1H), 7.58 (s, 1H), 7.42 (M, 4H), 6.45 (d, 1H), 6.37 (s, 2H) , 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 724(M+)MS / FAB: 724 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3):δ 8.36~8.35(m, 2H), 8.35(d, 1H), 7.98(s, 1H), 7.58~7.40(m, 3H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.83(t, 1H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 ~ 8.35 (m, 2H), 8.35 (d, 1H), 7.98 (s, 1H), 7.58 ~ 7.40 (m, 3H), 7.10 (t, 4H) , 6.95 (d, 1H), 6.37 (s, 1H), 1.68 (s, 1H) , ≪ / RTI > 6H), 1.62 (s, 6H)

MS/FAB: 620(M+)MS / FAB: 620 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 2H), 6.95~6.91(m, 6H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 5H), 6.37(s, 1H), 2.77(m, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.25(s, 9H), 1.10(d, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 2H), 6.95 6H), 6.71 (m, 3H), 6.53 (d, 2H), 6.45 (d, ), 1.62 (s, 6H), 1.25 (s, 9H), 1.10 (d, 6H)

MS/FAB: 716(M+)MS / FAB: < / RTI & gt ; 716 (M + )

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 3H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 4H), 6.95~6.89(m, 4H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 3H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 4H), 6.95 2H), 1.68 (s, 6H), 1.62 (s, 6H), 6.69 (d, )

MS/FAB: 619(M+)MS / FAB: 619 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.79(d, 1H), 7.58~7.56(m, 2H), 7.42~7.40(m, 2H), 7.28~6.97(m, 8H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 6.29(d, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.79 (d, 1H), 7.58 ~ 7.56 (m, 2H), 7.42 ~ 7.40 (m, 2H) , 7.28-6.97 (m, 8H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 4H), 6.53 (d, 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 708(M+)MS / FAB: 708 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.79(d, 1H), 7.58~7.56(m, 2H), 7.42~7.40(m, 2H), 7.28~7.10(m, 5H), 6.97~6.91(m, 5H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.45(d, 3H), 6.37(s, 1H), 6.29(d, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.25(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.79 (d, 1H), 7.58 ~ 7.56 (m, 2H), 7.42 ~ 7.40 (m, 2H) , 7.28-7.10 (m, 5H), 6.97-6.91 (m, 5H), 6.71-6.63 (m, 3H), 6.53 (d, 2H) (d, 1H), 1.68 (s, 6H), 1.62 (s, 6H), 1.25

MS/FAB: 764(M+)MS / FAB: 764 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.79(d, 1H), 7.58~7.56(m, 2H), 7.42~7.40(m, 2H), 7.29~7.10(m, 7H), 6.97~6.92(m, 3H), 6.71~6.63(m, 5H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 6.29(d, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.79 (d, 1H), 7.58 ~ 7.56 (m, 2H), 7.42 ~ 7.40 (m, 2H) , 7.29-7.10 (m, 7H), 6.97-6.92 (m, 3H), 6.71-6.63 (m, 5H), 6.53 (d, 2H), 6.45 (d, 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 733(M+)MS / FAB: 733 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.99~7.94(m, 3H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.26(t, 1H), 7.17(t, 1H), 7.10(t, 4H), 6.95~6.92(, 2H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.99 ~ 7.94 (m, 3H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.26 (t, 1H) , 7.17 (t, 1H), 7.10 (t, 4H), 6.95-6.92 (2H), 6.71-6.63 (m, 4H), 6.53 (d, 1H), 1.68 (s, 6H), 1.62 (s, 6H)

MS/FAB: 619(M+)MS / FAB: 619 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.05(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.37(m, 8H), 3.73(s, 3H), 1.68(s, 6H), 1.62(s, 6H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.05 (m, 4H) 6H), 1.62 (s, 6H), 0.15 (m, 2H), 6.95-6.92 (m, 2H), 6.71-6.63 (s, 9 H)

MS/FAB: 721(M+)MS / FAB: 721 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.05(m, 4H), 6.95~6.92(m, 2H), 6.71(t, 1H), 6.64~6.63(m, 2H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.05 (m, 4H) (M, 2H), 6.71 (m, 2H), 6.71 (t, 1H), 6.64 (s, 6 H), 0.15 (s, 9 H)

MS/FAB: 696(M+)MS / FAB: 696 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.05(m, 4H), 6.95~6.88(m, 4H), 6.71~6.63(m, 3H), 6.53~6.37(m, 8H), 2.24(s, 3H), 1.68(s, 6H), 1.62(s, 6H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.05 (m, 4H) , 6.95-6.88 (m, 4H), 6.71-6.63 (m, 3H), 6.53-6.37 (m, 8H) (s, 9 H)

MS/FAB: 705(M+)MS / FAB: 705 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.05(m, 4H), 6.95~6.91(m, 4H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.25(s, 9H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.05 (m, 4H) (S, 6H), 1.62 (s, 6H), 1.25 (s, 1H), 6.95-6.91 (m, 4H), 6.71-6.63 (s, 9 H), 0.15 (s, 9 H)

MS/FAB: 747(M+)MS / FAB: 747 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.05(m, 4H), 6.95~6.89(m, 4H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.05 (m, 4H) (S, 6H), 1.62 (s, 6H), 0.15 (m, 2H), 6.95-6.89 (m, 4H), 6.71-6.63 (s, 9 H)

MS/FAB: 708(M+)MS / FAB: 708 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.29(d, 2H), 7.10~7.05(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.51(m, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.29 (d, 2H), 7.10 2H), 6.71-6.63 (m, 5H), 6.53-6.51 (m, 4H), 6.45 (d, (s, 6H), 1.62 (s, 6H), 0.15 (s, 9H)

MS/FAB: 716(M+)MS / FAB: < / RTI & gt ; 716 (M + )

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98~7.92(m, 3H), 7.58(s, 1H), 7.47~7.40(m, 5H), 7.28(t, 1H), 7.10~7.05(m, 4H), 6.95~6.88(m, 3H), 6.71~6.63(m, 3H), 6.53~6.51(m, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 ~ 7.92 (m, 3H), 7.58 (s, 1H), 7.47 ~ 7.40 (m, 5H), 7.28 (t, 1H) (M, 4H), 6.95 (m, 4H), 6.95-6.88 (m, 3H), 6.71-6.63 , 1.68 (s, 6H), 1.62 (s, 6H), 0.15 (s, 9H)

MS/FAB: 741(M+)MS / FAB: 741 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.78~7.74(m, 2H), 7.67~7.64(m, 2H), 7.58(s, 1H), 7.42~7.39(m, 4H), 7.26(t, 1H), 7.10~7.05(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53~6.51(m, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 1H), 7.98 (d, 1H), 7.78 ~ 7.74 (m, 2H), 7.67 ~ 7.64 (m, 2H), 7.58 (s, 1H) , 7.42-7.39 (m, 4H), 7.26 (t, 1H), 7.10-7.05 (m, 4H), 6.95-6.92 (m, 2H), 6.71-6.63 (S, 6H), 1.62 (s, 6H), 0.15 (s, 9H)

MS/FAB: 741(M+)MS / FAB: 741 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.36(d, 1H), 7.98(d, 1H), 7.58(s, 1H), 7.44~7.31(m, 9H), 7.10~7.05(m, 4H), 6.95~6.92(m, 2H), 6.71~6.45(m, 10H), 6.37(s, 1H), 1.68(s, 6H), 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (d, IH), 7.98 (d, IH), 7.58 (s, IH), 7.44-7.31 (m, 9H), 7.10-7. , 6.95-6.92 (m, 2H), 6.71-6.45 (m, 10H), 6.37 (s,

1.62(s, 6H), 0.15(s, 9H)1.62 (s, 6H), 0.15 (s, 9H)

MS/FAB: 767(M+)MS / FAB: 767 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.86(m, 1H), 7.67(s, 1H), 7.61(m, 1H), 7.54~7.49(m, 3H), 7.37(m, 1H), 7.27(m, 1H), 7.19~7.14(m, 4H), 7.04~7.01(m, 2H), 6.80~6.72(m, 4H), 6.62~6.54(m, 6H), 6.46(s, 1H), 1.77~1.71(s, 18H), 0.24(s, 9H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (m, IH), 8.07 (m, IH), 7.86 (m, 2H), 6.80-6.72 (m, 4H), 6.62-6.44 (m, 2H), 7.37 (m, 6H), 6.46 (s, IH), 1.77-1.71 (s, 18H), 0.24

MS/FAB: 807(M+)MS / FAB: 807 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.86(m, 1H), 7.74(m, 2H), 7.67(s, 1H), 7.61(m, 1H), 7.54~7.51(m, 3H), 7.37~7.14(m, 12H), 7.04~7.01(m, 2H), 6.80~6.72(m, 4H), 6.62~6.54(m, 6H), 6.46(s, 1H), 1.77~1.71(s, 12H), 0.24(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.86 (m, 1H), 7.74 (m, 2H), 7.67 (s, 1H), 7.61 (m 2H), 6.80-6.72 (m, 4H), 6.62-6.44 (m, 6H), 6.46 (m, (s, 1H), 1.77-1.71 (s, 12H), 0.24 (s, 9H)

MS/FAB: 929(M+)MS / FAB: 929 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.86(m, 1H), 7.67(s, 1H), 7.61(m, 1H), 7.54~7.49(m, 3H), 7.32~7.10(m, 18H), 6.80~6.72(m, 4H), 6.62~6.54(m, 6H), 6.46(s, 1H), 1.77~1.71(s, 12H), 0.24(s, 9H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (m, IH), 8.07 (m, IH), 7.86 (m, 3H), 7.32-7.10 (m, 18H), 6.80-6.72 (m, 4H), 6.62-6.44 (m, 6H) (s, 9 H)

MS/FAB: 931(M+)MS / FAB: 931 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.19~7.14(m, 4H), 7.04~7.01(m, 4H), 6.80~6.72(m, 3H), 6.62~6.54(m, 7H), 6.46(s, 1H), 2.86(m, 1H), 1.77~1.71(s, 12H), 1.19(s, 6H), 0.24(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.19 ~ 7.14 (m, 4H) (M, 2H), 7.04-7.01 (m, 4H), 6.80-6.72 (m, 3H), 6.62-6.44 (m, , 1.19 (s, 6H), 0.24 (s, 9H)

MS/FAB: 733(M+)MS / FAB: 733 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.27~7.14(m, 6H), 7.04~7.01(m, 2H), 6.90(m, 1H), 6.80~6.71(m, 4H), 6.62~6.54(m, 5H), 6.46(s, 1H), 1.77~1.71(s, 12H), 0.24(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.27 ~ 7.14 (m, 6H) , 7.04-7.01 (m, 2H), 6.90 (m, 1H), 6.80-6.71 (m, 4H), 6.62-6.44 (m, , 0.24 (s, 9H)

MS/FAB: 716(M+)MS / FAB: < / RTI & gt ; 716 (M + )

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.36(m, 2H), 7.19~7.14(m, 4H), 7.04~7.01(m, 2H), 6.80~6.72(m, 3H), 6.62~6.54(m, 7H), 6.46(s, 1H), 1.77~1.71(s, 12H), 0.24(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.36 (m, 2H), 7.19 2H), 6.80-6.72 (m, 3H), 6.62-6.44 (m, 4H), 7.04-7.01 (m, 2H) , 0.24 (s, 9H)

MS/FAB: 758(M+)MS / FAB: 758 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45~8.44(m, 2H), 8.07(m, 1H), 7.97(m, 1H), 7.80(m, 1H), 7.67(s, 1H), 7.51~7.49(m, 4H), 7.26~7.14(m, 5H), 7.04~7.01(m, 2H), 6.85~6.72(m, 4H), 6.62~6.60(m, 5H), 6.46(s, 1H), 1.77~1.71(s, 12H), 0.24(s, 9H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45-8.44 (m, 2H), 8.07 (m, IH), 7.97 2H), 6.85-6.72 (m, 4H), 6.62-6.60 (m, 5H), 6.46 (s, 1H) , 1.77-1.71 (s, 12H), 0.24 (s, 9H)

MS/FAB: 797(M+)MS / FAB: 797 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.87(m, 1H), 7.67~7.65(m, 2H), 7.51~7.49(m, 2H), 7.37~7.01(m, 10H), 6.80~6.72(m, 3H), 6.62~6.54(m, 5H), 6.46(s, 1H), 6.38(m, 1H), 1.77~1.71(s, 12H), 0.24(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.87 (m, 1H), 7.67 ~ 7.65 (m, 2H), 7.51 ~ 7.49 (m, 2H) , 7.37-7.01 (m, 10H), 6.80-6.72 (m, 3H), 6.62-6.44 (m, 5H) , 0.24 (s, 9H)

MS/FAB: 781(M+)MS / FAB: 781 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.19(m, 2H), 7.04~6.98(m, 4H), 6.80~6.72(m, 5H), 6.62~6.51(m, 8H), 3.82(s, 3H), 1.77~1.71(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.19 (m, 2H), 7.04 (M, 4H), 6.80-6.72 (m, 5H), 6.62-6.51 (m, 8H)

MS/FAB: 666(M+)MS / FAB: 666 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.19(m, 2H), 7.04~6.98(m, 4H), 6.80~6.72(m, 3H), 6.62~6.54(m, 5H), 6.46(s, 1H), 1.77~1.71(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.19 (m, 2H), 7.04 1H), 1.77-1.71 (s, 12H), 6.62 (m, 2H)

MS/FAB: 641(M+)MS / FAB: 641 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.19(m, 2H), 7.04~6.97(m, 6H), 6.80~6.72(m, 3H), 6.62~6.46(m, 8H), 2.32(s, 3H), 1.77~1.71(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.19 (m, 2H), 7.04 6H), 6.80-6.72 (m, 3H), 6.62-6.46 (m, 8H), 2.32 (s, 3H), 1.77-1.71 (s, 12H)

MS/FAB: 650(M+)MS / FAB: 650 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.19(m, 2H), 7.04~6.98(m, 6H), 6.80~6.72(m, 3H), 6.62~6.54(m, 7H), 6.46(s, 1H), 1.77~1.71(s, 12H), 1.34(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.19 (m, 2H), 7.04 6H), 6.80-6.72 (m, 3H), 6.62-6.44 (m, 7H), 6.46 (s,

MS/FAB: 692(M+)MS / FAB: 692 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.38(m, 2H), 7.19(m, 2H), 7.04~6.98(m, 4H), 6.80~6.72(m, 5H), 6.62~6.54(m, 5H), 6.46(s, 1H), 1.77~1.71(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.38 (m, 2H), 7.19 (m, 2H), 7.04-6.98 (m, 4H), 6.80-6.72 (m, 5H), 6.62-6.44 (m,

MS/FAB: 661(M+)MS / FAB: 661 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07~8.01(m, 3H), 7.67(s, 1H), 7.56~7.49(m, 5H), 7.37(m, 1H), 7.19(m, 2H), 7.04~6.97(m, 5H), 6.80~6.72(m, 3H), 6.62~6.54(m, 5H), 6.46(s, 1H), 1.77~1.71(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 ~ 8.01 (m, 3H), 7.67 (s, 1H), 7.56 ~ 7.49 (m, 5H), 7.37 (m, 1H) , 7.19 (m, 2H), 7.04-6.97 (m, 5H), 6.80-6.72 (m, 3H), 6.62-6.44 (m,

MS/FAB: 686(M+)MS / FAB: 686 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.87~7.73(m, 4H), 7.67(s, 1H), 7.51~7.48(m, 4H), 7.35(m, 1H), 7.19(m, 2H), 7.04~6.98(m, 4H), 6.80~6.72(m, 3H), 6.54~6.60(m, 5H), 6.46(s, 1H), 1.77~1.71(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (m, IH), 8.07 (m, IH), 7.87-7.73 (m, 4H), 7.67 , 7.35 (m, 1H), 7.19 (m, 2H), 7.04-6.98 (m, 4H), 6.80-6.72 ~ 1.71 (s, 12H)

MS/FAB: 686(M+)MS / FAB: 686 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.53~7.40(m, 9H), 7.19(m, 2H), 7.04~6.98(m, 4H), 6.72~6.54(m, 10H), 6.46(s, 1H), 1.77~1.71(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.07 (m, 1H), 7.67 (s, 1H), 7.53 ~ 7.40 (m, 9H), 7.19 (m, 2H), 7.04 (M, 4H), 6.72-6.44 (m, 10H), 6.46 (s, 1H), 1.77-1.71

MS/FAB: 712(M+)MS / FAB: 712 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.07(m, 1H), 7.86(m, 1H), 7.67(s, 1H), 7.61(m, 1H), 7.54~7.49(m, 3H), 7.37(m, 1H), 7.27(m, 1H), 7.19(m, 2H), 7.04~6.98(m, 4H), 6.80~6.72(m, 4H), 6.62~6.54(m, 6H), 6.46(s, 1H), 1.77~1.71(s, 18H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (m, IH), 8.07 (m, IH), 7.86 (m, 3H), 7.37 (m, IH), 7.27 (m, IH), 7.19 (m, 2H), 7.04-6.998 (m, 4H), 6.80-6.72 , 6H), 6.46 (s, IH), 1.77-1.71 (s, 18H)

MS/FAB: 752(M+)MS / FAB: 752 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.86(d, 1H), 7.74(d, 2H), 7.67(s, 1H), 7.61~7.49(m, 4H), 7.37~7.15(m, 10H), 7.04~6.98(m, 4H), 6.80~6.72(m, 4H), 6.62~6.54(m, 6H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.86 (d, 1H), 7.74 (d, 2H), 7.67 (s, 1H), 7.61 ~ 7.49 (m, 4H), 7.37-7.15 (m, 10H), 7.04-6.98 (m, 4H), 6.80-6.72 (s, 6 H), 1.71 (s, 6 H)

MS/FAB: 875(M+)MS / FAB: 875 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.86(d, 1H), 7.67(s, 1H), 7.61~7.49(m, 4H), 7.37~6.98(m, 18H), 6.80~6.72(m, 4H), 6.62~6.54(m, 6H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.86 (d, 1H), 7.67 (s, 1H), 7.61 ~ 7.49 (m, 4H), 7.37 6H), 1.77 (s, 6H), 1.71 (s, 6H), 6.71 (s,

MS/FAB: 877(M+)MS / FAB: 877 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.19(m, 2H), 7.04~6.98(m, 6H), 6.80~6.72(m, 3H), 6.62~6.54(m, 7H), 6.46(s, 1H), 2.86(m, 1H), 1.77(s, 6H), 1.71(s, 6H), 1.19(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.19 (m, 2H), 7.04 2H), 1.77 (s, 6H), 1.71 (s, 2H), 6.82 (m, , ≪ / RTI > 6H), 1.19 (s, 6H)

MS/FAB: 678(M+)MS / FAB: 678 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.27~7.19(m, 4H), 7.04~6.90(m, 5H), 6.80~6.71(m, 4H), 6.62~6.54(m, 5H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.27 ~ 7.19 (m, 4H) , 7.04-6.90 (m, 5H), 6.80-6.71 (m, 4H), 6.62-6.44 (m, 5H)

MS/FAB: 661(M+)MS / FAB: 661 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.36(d, 2H), 7.19(m, 2H), 7.04~6.98(m, 4H), 6.80~6.72(m, 3H), 6.62~6.54(m, 7H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.36 (d, 2H), 7.19 (m, 2H), 7.04-6.98 (m, 4H), 6.80-6.72 (m, 3H), 6.62-6.44 , 6H)

MS/FAB: 704(M+)MS / FAB: 704 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3): δ 8.45~8.44(m, 2H), 8.07(d, 1H), 7.97(d, 1H), 7.80(d, 1H), 7.67(s, 1H), 7.51~7.49(m, 4H), 7.26~7.19(m, 3H), 7.04~6.98(m, 4H), 6.85~6.72(m, 4H), 6.62~6.54(m, 5H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45-8.44 (m, 2H), 8.07 (d, IH), 7.97 4H), 6.62-6.44 (m, 4H), 6.62-6.44 (m, 4H), 7.26-7.19 (m, 3H), 7.04-6.98 , 1.77 (s, 6 H), 1.71 (s, 6 H)

MS/FAB: 742(M+)MS / FAB: 742 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.88(d, 1H), 7.67~7.65(m, 2H), 7.51~7.49(m, 2H), 7.37~7.19(m, 5H), 7.06~6.98(m, 5H), 6.80~6.72(m, 3H), 6.62~6.54(m, 5H), 6.46(s, 1H), 6.38(d, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.88 (d, 1H), 7.67 ~ 7.65 (m, 2H), 7.51 ~ 7.49 (m, 2H) , 7.37-7.19 (m, 5H), 7.06-6.98 (m, 5H), 6.80-6.72 (m, 3H), 6.62-6.44 , 1.77 (s, 6 H), 1.71 (s, 6 H)

MS/FAB: 726(M+)MS / FAB: 726 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.38(m, 2H), 7.19(m, 2H), 7.04~7.01(m, 2H), 6.80~6.72(m, 7H), 6.62(m, 2H), 6.54~6.46(m, 4H), 3.82(s, 3H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.38 (m, 2H), 7.19 (m, 2H), 7.04-7.01 (m, 2H), 6.80-6.72 (m, 7H), 6.62 (m, 2H), 6.54-6.46 , ≪ / RTI > 6H), 1.71 (s, 6H)

MS/FAB: 673(M+)MS / FAB: 673 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.38(m, 2H), 7.19(m, 2H), 7.04~7.01(m, 2H), 6.80~6.72(m, 5H), 6.62(m, 2H), 6.54(d, 1H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.38 (m, 2H), 7.19 (m, 2H), 7.04-7.01 (m, 2H), 6.80-6.72 (m, 5H), 6.62 (m, 2H), 6.54 ), 1.71 (s, 6H)

MS/FAB: 648(M+)MS / FAB: 648 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.38(m, 2H), 7.19(m, 2H), 7.04~6.97(m, 4H), 6.80~6.72(m, 5H), 6.62(m, 2H), 6.54~6.46(m, 4H), 2.33(s, 3H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.38 (m, 2H), 7.19 (m, 2H), 7.04-6.97 (m, 4H), 6.80-6.72 (m, 5H), 6.62 (m, 2H), 6.54-6.46 , ≪ / RTI > 6H), 1.71 (s, 6H)

MS/FAB: 657(M+)MS / FAB: 657 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.67(s, 1H), 7.51~7.49(m, 2H), 7.38(m, 2H), 7.19(m, 2H), 7.04~7.00(m, 4H), 6.80~6.72(m, 5H), 6.62(m, 2H), 6.54(m, 3H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H), 1.34(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.67 (s, 1H), 7.51 ~ 7.49 (m, 2H), 7.38 (m, 2H), 7.19 (m, 2H), 7.04-7.00 (m, 4H), 6.80-6.72 (m, 5H), 6.62 ), 1.71 (s, 6 H), 1.34 (s, 9 H)

MS/FAB: 699(M+)MS / FAB: 699 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07~8.01(m, 3H), 7.67(s, 1H), 7.56~7.49(m, 5H), 7.38~7.37(m, 3H), 7.19(m, 2H), 7.04~6.97(m, 3H), 6.80~6.72(m, 5H), 6.62(m, 2H), 6.54(m, 1H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 ~ 8.01 (m, 3H), 7.67 (s, 1H), 7.56 ~ 7.49 (m, 5H), 7.38 ~ 7.37 (m, (M, 2H), 7.14 (m, 2H), 7.04-6.97 (m, 3H), 6.80-6.72 (s, 6 H), 1.71 (s, 6 H)

MS/FAB: 693(M+)MS / FAB: 693 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(m, 1H), 7.87~7.73(m, 4H), 7.67(s, 1H), 7.51~7.48(m, 4H), 7.38~7.35(m, 3H), 7.19(m, 2H), 7.04~7.01(m, 2H), 6.80~6.72(m, 5H), 6.62(m, 2H), 6.54(m, 1H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (m, 1H), 7.87 ~ 7.73 (m, 4H), 7.67 (s, 1H), 7.51 ~ 7.48 (m, 4H) (M, 2H), 7.04 (m, 2H), 6.80-6.72 (m, 2H) (s, 1 H), 1.77 (s, 6 H), 1.71 (s, 6 H)

MS/FAB: 693(M+)MS / FAB: 693 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(m, 1H), 7.67(s, 1H), 7.53~7.38(m, 11H), 7.19(m, 2H), 7.04~7.01(m, 2H), 6.80~6.62(m, 9H), 6.54(m, 1H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (d, IH), 8.07 (m, IH), 7.67 6H), 1.71 (s, 6H), 7.01 (m, 2H), 6.80-6.62 (m, 9H), 6.54

MS/FAB: 719(M+)MS / FAB: 719 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(m, 1H), 7.86(d, 1H), 7.67(s, 1H), 7.61(d, 1H), 7.54~7.49(m, 3H), 7.38~7.37(m, 3H), 7.27~7.19(m, 3H), 7.04~7.01(m, 2H), 6.80~6.72(m, 6H), 6.62~6.54(m, 4H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (d, IH), 8.07 (m, IH), 7.86 (m, 3H), 7.38-7.37 (m, 3H), 7.27-7.19 (m, 3H), 7.04-7.01 (m, 2H), 6.80-6.72 , 6.46 (s, 1 H), 1.77 (s, 6 H), 1.71 (s, 12 H)

MS/FAB: 759(M+)MS / FAB: 759 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(m, 1H), 7.86(d, 1H), 7.74(m, 2H), 7.67(s, 1H), 7.61~7.49(m, 4H), 7.38~7.15(m, 12H), 7.04~7.01(m, 2H), 6.80~6.72(m, 6H), 6.62~6.54(m, 4H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (d, IH), 8.07 (m, IH), 7.86 (m, 4H), 7.36-7.15 (m, 12H), 7.04-7.01 (m, 2H), 6.80-6.72 (s, 6 H), 1.71 (s, 6 H)

MS/FAB: 882(M+)MS / FAB: 882 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(m, 1H), 7.86(d, 1H), 7.67(s, 1H), 7.61~7.49(m, 4H), 7.38~7.01(m, 18H), 6.80~6.72(m, 6H), 6.62~6.54(m, 4H), 6.46(s, 1H), 1.77(s, 6H), 1.71(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (m, 1H), 7.86 (d, 1H), 7.67 (s, 1H), 7.61 ~ 7.49 (m, 4H), 7.38 (S, 6H), 1.71 (s, 6H), 7.01 (m, 18H), 6.80-6.72

MS/FAB: 884(M+)MS / FAB: 884 (M < + & gt ; ).

[합성예103] 화합물 [103]의 합성[Synthesis Example 103] Synthesis of compound [103]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.29(d, 2H), 7.10(t, 2H), 6.95~6.92(m, 4H), 6.71~6.63(m, 5H), 6.53~6.45(m, 5H), 6.37(s, 1H), 2.77(m, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.10(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.29 (d, 2H), 7.10 (m, 2H), 6.95-6.92 (m, 4H), 6.71-6.63 (m, 5H), 6.53-6.45 , 6H), 1.62 (s, 6H), 1.10 (s, 6H)

MS/FAB: 685(M+)MS / FAB: 685 (M < + & gt ; ).

[합성예104] 화합물 [104]의 합성[Synthesis Example 104] Synthesis of compound [104]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.29(d, 2H), 7.18~7.10(m, 4H), 6.95~6.92(m, 2H), 6.81(m, 1H), 6.71~6.62(m, 6H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.29 (d, 2H), 7.18 (D, 2H), 6.45 (d, 1H), 6.37 (s, 2H), 6.95 , 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 668(M+)MS / FAB: 668 (M < + & gt ; ).

[합성예105] 화합물 [105]의 합성[Synthesis Example 105] Synthesis of compound [105]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.29~7.27(m, 4H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.29 ~ 7.27 (m, 4H) (M, 2H), 7.10 (t, 2H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 5H), 6.53-6.45 (s, 6 H)

MS/FAB: 711(M+)MS / FAB: 711 (M < + & gt ; ).

[합성예106] 화합물 [106]의 합성[Synthesis Example 106] Synthesis of Compound [106]

1H NMR (300 MHz, CDCl3):δ 8.36~8.35(m, 2H), 7.98(m, 1H), 7.88(m, 1H), 7.71(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 4H), 7.29(d, 2H), 7.17~7.10(m, 3H), 6.95~6.92(m, 2H), 6.76~6.63(m, 6H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 ~ 8.35 (m, 2H), 7.98 (m, 1H), 7.88 (m, 1H), 7.71 (d, 1H), 7.58 (s, 1H), 7.42 2H), 6.76-6.63 (m, 6H), 6.53 (d, 2H), 6.45 (m, 2H) (d, IH), 6.37 (s, IH), 1.68 (s, 6H), 1.62

MS/FAB: 749(M+)MS / FAB: 749 (M < + & gt ; ).

[합성예107] 화합물 [107]의 합성[Synthesis Example 107] Synthesis of Compound [107]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.79(d, 1H), 7.58~7.56(m, 2H), 7.42~7.40(m, 2H), 7.29~7.10(m, 7H), 6.95~6.92(m, 3H), 6.71~6.63(m, 5H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 6.29(d, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.79 (d, 1H), 7.58 ~ 7.56 (m, 2H), 7.42 ~ 7.40 (m, 2H) , 7.29-7.10 (m, 7H), 6.95-6.92 (m, 3H), 6.71-6.63 (m, 5H), 6.53 (d, 2H), 6.45 (d, 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 733(M+)MS / FAB: 733 (M < + & gt ; ).

[합성예108] 화합물 [108]의 합성[Synthesis Example 108] Synthesis of Compound [108]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.27(d, 2H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.37(m, 8H), 3.73(s, 3H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.27 (d, 2H), 7.10 (m, 2H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 5H), 6.53-6.37 , 6H)

MS/FAB: 716(M+)MS / FAB: < / RTI & gt ; 716 (M + )

[합성예109] 화합물 [109]의 합성[Synthesis Example 109] Synthesis of Compound [109]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.27(d, 2H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53~6.46(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.27 (d, 2H), 7.10 (m, 2H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 3H), 6.53-6.46 , 6H)

MS/FAB: 691(M+)MS / FAB: 691 (M < + & gt ; ).

[합성예110] 화합물 [110]의 합성[Synthesis Example 110] Synthesis of Compound [110]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.27(d, 2H), 7.10(t, 2H), 6.95~6.88(m, 4H), 6.71~6.63(m, 3H), 6.53~6.37(m, 8H), 2.24(s, 3H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.27 (d, 2H), 7.10 (s, 3H), 1.68 (s, 6H), 1.62 (s, 2H), 6.95-6.88 (m, 4H), 6.71-6.63 , 6H)

MS/FAB: 700(M+)MS / FAB: 700 (M @ + )

[합성예111] 화합물 [111]의 합성[Synthesis Example 111] Synthesis of Compound [111]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.27(d, 2H), 7.10(t, 2H), 6.95~6.91(m, 4H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.25(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.27 (d, 2H), 7.10 (s, 6H), 1.62 (s, 2H), 6.95-6.91 (m, 4H), 6.71-6.63 (m, 3H), 6.53-6.45 , ≪ / RTI > 6H), 1.25 (s, 9H)

MS/FAB: 742(M+)MS / FAB: 742 (M < + & gt ; ).

[합성예112] 화합물 [112]의 합성[Synthesis Example 112] Synthesis of Compound [112]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98~7.92(m, 3H), 7.58(s, 1H), 7.47~7.40(m, 5H), 7.28~7.27(m, 3H), 7.10(t, 2H), 6.95~6.91(m, 3H), 6.71~6.63(m, 3H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 ~ 7.92 (m, 3H), 7.58 (s, 1H), 7.47 ~ 7.40 (m, 5H), 7.28 ~ 7.27 (m, (M, 3H), 6.53-6.45 (m, 5H), 6.37 (s, IH), 1.68 (s, 6H) , 1.62 (s, 6H)

MS/FAB: 736(M+)MS / FAB: 736 (M < + & gt ; ).

[합성예113] 화합물 [113]의 합성[Synthesis Example 113] Synthesis of Compound [113]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.78~7.64(m, 4H), 7.58(s, 1H), 7.42~7.39(m, 4H), 7.27~7.26(m, 3H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (m, IH), 7.98 (m, IH), 7.78-7.64 , 7.27-7.26 (m, 3H), 7.10 (t, 2H), 6.95-6.92 (m, 2H), 6.71-6.63 , 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 736(M+)MS / FAB: 736 (M < + & gt ; ).

[합성예114] 화합물 [114]의 합성[Synthesis Example 114] Synthesis of Compound [114]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.31(m, 11H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.45(m, 10H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.31 (m, 11H), 7.10 (t, 2H), 6.95 1H), 1.68 (s, 6H), 1.62 (s, 6H)

MS/FAB: 762(M+)MS / FAB: 762 (M < + & gt ; ).

[합성예115] 화합물 [115]의 합성[Synthesis Example 115] Synthesis of Compound [115]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.77(d, 1H), 7.58(s, 1H), 7.52(d, 1H), 7.45~7.40(m, 3H), 7.28~7.27(m, 3H), 7.18~7.10(m, 3H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.77 (d, 1H), 7.58 (s, 1H), 7.52 (d, 1H), 7.45 ~ 7.40 (m, 3H), 7.28-7.27 (m, 3H), 7.18-7.10 (m, 3H), 6.95-6.92 (m, 2H), 6.71-6.63 , 6.37 (s, 1 H), 1.68 (s, 6 H), 1.62 (s, 12 H)

MS/FAB: 802(M+)MS / FAB: 802 (M < + & gt ; ).

[합성예116] 화합물 [116]의 합성[Synthesis Example 116] Synthesis of Compound [116]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.77(d, 1H), 7.65(d, 2H), 7.58(s, 1H), 7.52~7.40(m, 4H), 7.28~7.10(m, 12H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (m, IH), 7.98 (m, IH), 7.77 (m, 4H), 7.28-7.10 (m, 12H), 6.95-6.92 (m, 2H), 6.71-6.63 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 925(M+)MS / FAB: 925 (M < + & gt ; ) [

[합성예117] 화합물 [117]의 합성[Synthesis Example 117] Synthesis of Compound [117]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.77(d, 1H), 7.58(s, 1H), 7.52~7.45(m, 4H), 7.28~6.92(m, 18H), 6.71~6.63(m, 4H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.77 (d, 1H), 7.58 (s, 1H), 7.52 ~ 7.45 (m, 4H), 7.28 6H), 1.62 (s, 6H), 1.62 (s, 6H), 6.62 (s,

MS/FAB: 927(M+)MS / FAB: 927 (M < + & gt ; ).

[합성예118] 화합물 [118]의 합성[Synthesis Example 118] Synthesis of Compound [118]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.27(d, 2H), 7.10(t, 2H), 6.95~6.92(m, 4H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 2.77(m, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.10(d, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.27 (d, 2H), 7.10 (m, 2H), 6.95-6.92 (m, 4H), 6.71-6.63 (m, 3H), 6.53-6.45 , 6H), 1.62 (s, 6H), 1.10 (d, 6H)

MS/FAB: 728(M+)MS / FAB: 728 (M < + & gt ; ).

[합성예119] 화합물 [119]의 합성[Synthesis Example 119] Synthesis of Compound [119]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.27(d, 2H), 7.18~7.10(m, 4H), 6.95~6.92(m, 2H), 6.81(m, 1H), 6.71~6.62(m, 4H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.27 (d, 2H), 7.18 2H), 6.81 (m, 1H), 6.71-6.62 (m, 4H), 6.53-6.45 (m, 5H), 6.37 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 711(M+)MS / FAB: 711 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36~8.35(m, 2H), 7.98(m, 1H), 7.88(m, 1H), 7.71(d, 1H), 7.58(s, 1H), 7.42~7.40(m, 4H), 7.27(d, 2H), 7.17~7.10(m, 3H), 6.95~6.92(m, 2H), 6.76~6.63(m, 4H), 6.53(d, 2H), 6.46~6.45(m, 3H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 ~ 8.35 (m, 2H), 7.98 (m, 1H), 7.88 (m, 1H), 7.71 (d, 1H), 7.58 (s, 1H), 7.42 2H), 6.76-6.63 (m, 4H), 6.53 (d, 2H), 6.46 (m, 2H) 1H), 1.68 (s, 6H), 1.62 (s, 6H)

MS/FAB: 793(M+)MS / FAB: 793 (M < + >) [

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.79(d, 1H), 7.58(s, 1H), 7.56(d, 1H), 7.42~7.40(m, 2H), 7.28~7.22(m, 4H), 7.15~7.10(m, 3H), 6.97~6.92(m, 3H), 6.71~6.63(m, 3H), 6.53(d, 2H), 6.46~6.45(d, 3H), 6.37(s, 1H), 6.29(d, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (m, IH), 7.98 (m, IH), 7.79 (d, IH), 7.58 (m, 3H), 6.71-6.63 (m, 3H), 6.53 (d, 2H), 6.46 (m, 2H), 7.28-7.22 6H), 1.62 (s, 6H), 6.68 (s, 2H)

MS/FAB: 777(M+)MS / FAB: 777 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 1H), 8.36~8.32(m, 2H), 7.98~7.94(m, 3H), 7.58(s, 1H), 7.51~7.40(m, 5H), 7.10~7.07(t, 5H), 6.99~6.92(m, 3H), 6.71~6.53(m, 9H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.36 ~ 8.32 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.58 (s, 1H), 7.51 ~ 7.40 (m, (S, 6H), 6.70 (s, 2H), 6.30 (s, 2H) , 1.62 (s, 6H)

MS/FAB: 770(M+)MS / FAB: 770 (M < + >) [

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 1H), 8.36~8.32(m, 2H), 7.98~7.94(m, 3H), 7.58(s, 1H), 7.51~7.40(m, 6H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.80~6.79(m, 2H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.36 ~ 8.32 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.58 (s, 1H), 7.51 ~ 7.40 (m, 2H), 6.71-6.63 (m, 4H), 6.53 (d, 4H), 6.45 (m, 2H), 6.95-6.92 , 6.37 (s, 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 813(M+)MS / FAB: 813 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.79~7.71(m, 3H), 7.58~7.56(m, 2H), 7.44~7.40(m, 3H), 7.28~7.22(m, 3H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.80~6.79(m, 2H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.79 ~ 7.71 (m, 3H), 7.58 ~ 7.56 (m, 2H), 7.44 ~ 7.40 (m, 2H), 6.71-6.63 (m, 4H), 6.53 (d, 3H), 7.28-7.22 (m, 3H) 6H), 1.62 (s, 6H), 1.68 (d, IH)

MS/FAB: 853(M+)MS / FAB: < / RTI > 853 (M +)

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 1H), 8.36~8.32(m, 2H), 7.98~7.94(m, 3H), 7.58(s, 1H), 7.51~7.40(m, 5H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.78~6.53(m, 10H), 6.45~6.43(m, 2H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.36 ~ 8.32 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.58 (s, 1H), 7.51 ~ 7.40 (m, 2H), 6.37 (s, IH), 1.68 (s, 6H), 6.90 (m, 2H) , 1.62 (s, 6H)

MS/FAB: 763(M+)MS / FAB: 763 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.79~7.71(m, 3H), 7.58~7.56(m, 2H), 7.42~7.40(m, 2H), 7.28~7.22(m, 3H), 7.10~7.07(t, 5H), 6.99~6.92(m, 3H), 6.71~6.58(m, 5H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.79 ~ 7.71 (m, 3H), 7.58 ~ 7.56 (m, 2H), 7.42 ~ 7.40 (m, 2H), 7.28-7.22 (m, 3H), 7.10-7.07 (t, 5H), 6.99-6.92 (m, 3H), 6.71-6.58 1H), 6.37 (s, IH), 1.68 (s, 6H), 1.62 (s, 6H)

MS/FAB: 810(M+)MS / FAB: 810 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36~8.31(m, 3H), 8.10(d, 1H), 7.98(m, 1H), 7.88(m, 1H), 7.58(s, 1H), 7.48~7.40(m, 6H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.80~6.79(m, 2H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 ~ 8.31 (m, 3H), 8.10 (d, 1H), 7.98 (m, 1H), 7.88 (m, 1H), 7.58 (s, 1H), 7.48 2H), 6.71-6.63 (m, 4H), 6.53 (d, 4H), 6.45 (m, 2H) (d, IH), 6.37 (s, IH), 1.68 (s, 6H), 1.62

MS/FAB: 869(M+)MS / FAB: 869 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.79~7.71(m, 3H), 7.58~7.56(m, 2H), 7.42~7.40(m, 2H), 7.28~7.22(m, 3H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.78~6.53(m, 10H), 6.45~6.43(m, 2H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.79 ~ 7.71 (m, 3H), 7.58 ~ 7.56 (m, 2H), 7.42 ~ 7.40 (m, 2H), 6.37 (s, 2H), 7.28-7.22 (m, 3H), 7.10 (t, 4H), 6.95-6.92 1H), 1.68 (s, 6H), 1.62 (s, 6H)

MS/FAB: 803(M+)MS / FAB: 803 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.90(m, 2H), 7.82(d, 1H), 7.63(d, 1H), 7.58(s, 1H), 7.49~7.48(m, 3H), 7.42~7.40(m, 2H), 7.10~7.07(t, 5H), 6.99~6.92(m, 3H), 6.71~6.63(m, 5H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.90 (m, 2H), 7.82 (d, 1H), 7.63 (d, 1H), 7.58 (s 2H), 7.10-7.07 (t, 5H), 6.99-6.92 (m, 3H), 6.71-6.63 (m, 5H), 6.53 (d, IH), 6.45 (d, IH), 6.37 (s, IH)

MS/FAB: 770(M+)MS / FAB: 770 (M < + >) [

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.90(m, 2H), 7.82(d, 1H), 7.63(d, 1H), 7.58(s, 1H), 7.49~7.48(m, 3H), 7.45~7.40(m, 3H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.80~6.79(m, 2H), 6.71(t, 2H), 6.63(t, 2H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.90 (m, 2H), 7.82 (d, 1H), 7.63 (d, 1H), 7.58 (s 2H), 6.80-6.79 (m, 2H), 6.71 (m, 2H), 7.47-7.40 (m, 3H) 2H), 6.63 (t, 2H), 6.53 (d, 4H), 6.45 (s,

MS/FAB: 813(M+)MS / FAB: 813 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.90(m, 2H), 7.82(d, 1H), 7.63(d, 1H), 7.58(s, 1H), 7.49~7.48(m, 3H), 7.42~7.40(m, 2H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.78(d, 1H), 6.71~6.63(m, 5H), 6.53(m, 4H), 6.45~6.43(m, 2H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.90 (m, 2H), 7.82 (d, 1H), 7.63 (d, 1H), 7.58 (s 2H), 6.78 (d, 1H), 6.71-6.63 (m, 2H), 7.49 (m, 2H), 6.37 (s, 1H), 1.68 (s, 6H), 1.62 (s, 6H)

MS/FAB: 763(M+)MS / FAB: 763 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 8H), 7.31(m, 2H), 7.13~7.10(m, 6H), 6.98~6.92(m, 4H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 8H), 7.31 (m, 2H), 7.13 1H), 6.37 (s, 1H), 1.68 (s, 1H), 7.90 (d, , ≪ / RTI > 6H), 1.62 (s, 6H)

MS/FAB: 789(M+)MS / FAB: 789 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.63(s, 1H), 7.58(s, 1H), 7.42~7.40(m, 8H), 7.34~7.31(m, 3H), 7.10(t, 4H), 6.98~6.92(m, 4H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.63 (s, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 8H), 7.34 (M, 4H), 6.53 (d, 4H), 6.45 (d, 1H), 6.37 (s, , 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 796(M+)MS / FAB: 796 (M < + >) [

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.79(s, 1H), 7.58(s, 1H), 7.42~7.40(m, 8H), 7.35~7.31(m, 3H), 7.10(t, 4H), 6.98~6.92(m, 4H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.79 (s, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 8H), 7.35 (M, 4H), 6.53 (d, 4H), 6.45 (d, 1H), 6.37 (s, , 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 839(M+)MS / FAB: < / RTI > 839 (M +)

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 4H), 6.95~6.91(m, 4H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 3H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.25(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 4H), 6.95 6H), 1.68 (s, 6H), 1.62 (s, 6H), 6.71 (d, ), 1.25 (s, 9H)

MS/FAB: 675(M+)MS / FAB: 675 (M < + >).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.18~7.17(d, 2H), 7.10(t, 2H), 6.95~6.91(m, 4H), 6.81(m, 1H), 6.71~6.62(m, 4H), 6.53(d, 2H), 6.45(d, 3H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.25(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.18 ~ 7.17 (d, 2H) 2H), 6.95 (m, 4H), 6.81 (m, 4H), 6.71 , 1.68 (s, 6H), 1.62 (s, 6H), 1.25 (s, 9H)

MS/FAB: 700(M+)MS / FAB: 700 (M @ +)

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.18(d, 1H), 7.78(s, 1H), 7.62~7.60(m, 2H), 7.30~7.23(m, 3H), 7.15~7.04(m, 6H), 6.91~6.83(m, 3H), 6.73(d, 3H), 6.65(d, 3H), 6.57(s, 1H), 1.88~1.82(d, 12H), 1.45(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.18 (d, 1H), 7.78 (s, 1H), 7.62 ~ 7.60 (m, 2H), 7.30 ~ 7.23 (m, 3H) , 7.15-7.04 (m, 6H), 6.91-6.83 (m, 3H), 6.73 (d, 3H), 6.65 (s, 9 H)

MS/FAB: 743(M+)MS / FAB: 743 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.18(d, 1H), 7.78(s, 1H), 7.62~7.60(m, 2H), 7.30~7.28(m, 3H), 7.15~7.11(m, 4H), 6.91~6.83(m, 3H), 6.70~6.65(m, 7H), 6.57(s, 1H), 6.50(d, 1H), 1.88~1.82(d, 12H), 1.45(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.18 (d, 1H), 7.78 (s, 1H), 7.62 ~ 7.60 (m, 2H), 7.30 ~ 7.28 (m, 3H) , 7.15-7.11 (m, 4H), 6.91-6.83 (m, 3H), 6.70-6.65 (m, 7H), 6.57 (s, , 1.45 (s, 9H)

MS/FAB: 693(M+)MS / FAB: 693 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.56(m, 1H), 8.18~8.17(m, 3H), 7.78(s, 1H), 7.65~7.60(m, 4H), 7.15~7.11(m, 4H), 6.83~6.65(m, 9H), 6.57(s, 1H), 1.88~1.82(d, 12H), 1.45(s, 9H) 1 H NMR (300 MHz, CDCl 3 ):? 8.56 (m, 1 H), 8.18-8.17 (m, 3H), 7.78 4H), 6.83-6.65 (m, 9H), 6.57 (s, 1H), 1.88-1.82

MS/FAB: 677(M+)MS / FAB: 677 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3): δ 8.65(m, 1H), 8.56~8.52(m, 2H), 8.18~8.14(m, 3H), 7.78(s, 1H), 7.71~7.60(m, 5H), 7.30~7.27(m, 3H), 7.19~7.11(m, 5H), 6.91~6.73(m, 6H), 6.65(d, 3H), 6.57(s, 1H), 1.88~1.82(d, 12H), 1.45(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.65 (m, 1H), 8.56 ~ 8.52 (m, 2H), 8.18 ~ 8.14 (m, 3H), 7.78 (s, 1H), 7.71 ~ 7.60 (m, 6H), 6.65 (d, 3H), 6.57 (s, 1H), 1.88-1.82 (d, 3H), 7.30-7.27 (m, 12H), 1.45 (s, 9H)

MS/FAB: 826(M+)MS / FAB: 826 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.65(m, 1H), 8.56~8.52(m, 2H), 8.18~8.14(m, 3H), 7.78(s, 1H), 7.71~7.60(m, 6H), 7.30(t, 2H), 7.15~7.11(m, 4H), 7.10~6.99(s, 2H), 6.91~6.83(m, 3H), 6.73(d, 2H), 6.65(d, 3H), 6.57(s, 1H), 1.88~1.82(d, 12H), 1.45(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.65 (m, 1H), 8.56 ~ 8.52 (m, 2H), 8.18 ~ 8.14 (m, 3H), 7.78 (s, 1H), 7.71 ~ 7.60 (m, 2H), 6.65 (d, 2H), 7.30 (t, 2H), 7.15-7.11 (m, 4H), 7.10-6.99 (s, 2H), 6.91-6.83 , 6.57 (s, 1H), 1.88-1.82 (d, 12H), 1.45 (s, 9H)

MS/FAB: 869(M+)MS / FAB: 869 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.65(m, 1H), 8.56~8.52(m, 2H), 8.18~8.14(m, 3H), 7.78(s, 1H), 7.71~7.60(m, 5H), 7.30(t, 2H), 7.15~7.11(m, 4H), 6.98~6.73(m, 7H), 6.65~6.63(m, 4H), 6.57(s, 1H), 1.88~1.82(d, 12H), 1.45(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.65 (m, 1H), 8.56 ~ 8.52 (m, 2H), 8.18 ~ 8.14 (m, 3H), 7.78 (s, 1H), 7.71 ~ 7.60 (m, (D, 2H), 7.15-7.11 (m, 4H), 6.98-6.73 (m, 7H), 6.65-6.63 12H), 1.45 (s, 9H)

MS/FAB: 819(M+)MS / FAB: 819 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.13(d, 1H), 7.78(s, 1H), 7.62~7.60(m, 2H), 7.30~7.25(m, 6H), 7.15~7.12(m, 2H), 6.91~6.83(m, 4H), 6.73~6.65(m, 7H), 6.57(s, 1H), 1.88~1.82(d, 12H), 0.35(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.13 (d, 1H), 7.78 (s, 1H), 7.62 ~ 7.60 (m, 2H), 7.30 ~ 7.25 (m, 6H) (S, 9H), 7.15-7.12 (m, 2H), 6.91-6.83 (m, 4H), 6.73-6.65

MS/FAB: 691(M+)MS / FAB: 691 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.13(d, 1H), 7.78(s, 1H), 7.62~7.60(m, 2H), 7.38~7.25(m, 6H), 7.15~7.12(m, 2H), 7.01(m, 1H), 6.91~6.82(m, 4H), 6.73~6.65(m, 5H), 6.57(s, 1H), 1.88~1.82(d, 12H), 0.35(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.13 (d, 1H), 7.78 (s, 1H), 7.62 ~ 7.60 (m, 2H), 7.38 ~ 7.25 (m, 6H) (M, 2H), 7.01 (m, 1H), 6.91-6.82 (m, 4H), 6.73-6.65 , 0.35 (s, 9H)

MS/FAB: 716(M+)MS / FAB: < / RTI & gt ; 716 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.18(d, 1H), 7.78(s, 1H), 7.62~7.60(m, 2H), 7.30~7.23(m, 5H), 7.15~7.04(m, 4H), 6.91~6.83(m, 3H), 6.71~6.65(m, 6H), 6.57(s, 1H), 1.88~1.82(d, 12H), 0.35(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.18 (d, 1H), 7.78 (s, 1H), 7.62 ~ 7.60 (m, 2H), 7.30 ~ 7.23 (m, 5H) , 7.15-7.04 (m, 4H), 6.91-6.83 (m, 3H), 6.71-6.65 (m, 6H), 6.57 (s,

MS/FAB: 759(M+)MS / FAB: 759 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.18(d, 1H), 7.78(s, 1H), 7.62~7.60(m, 2H), 7.30~7.25(m, 5H), 7.15~7.12(m, 2H), 6.91~6.83(m, 3H), 6.73~6.65(m, 7H), 6.57(s, 1H), 6.50(d, 1H), 1.88~1.82(d, 12H), 0.35(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.18 (d, 1H), 7.78 (s, 1H), 7.62 ~ 7.60 (m, 2H), 7.30 ~ 7.25 (m, 5H) (D, 1H), 7.18-7.12 (m, 2H), 6.91-6.83 (m, 3H), 6.73-6.65 , 0.35 (s, 9H)

MS/FAB: 709(M+)MS / FAB: 709 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.18~8.17(m, 3H), 7.78(s, 1H), 7.65~7.60(m, 4H), 7.25(d, 2H), 7.15~7.12(m, 2H), 6.83~6.65(m, 9H), 6.57(s, 1H), 1.88~1.82(d, 12H), 0.35(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.18 ~ 8.17 (m, 3H), 7.78 (s, 1H), 7.65 ~ 7.60 (m, 4H), 7.25 (d, 2H) (S, 9H), 7.15-7.12 (m, 2H), 6.83-6.65 (m, 9H)

MS/FAB: 693(M+)MS / FAB: 693 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.65(m, 1H), 8.56~8.52(m, 2H), 8.18~8.14(m, 3H), 7.78(s, 1H), 7.71~7.60(m, 5H), 7.30~7.12(m, 8H), 6.83~6.65(m, 9H), 6.57(s, 1H), 1.88~1.82(d, 12H), 0.35(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.65 (m, 1H), 8.56 ~ 8.52 (m, 2H), 8.18 ~ 8.14 (m, 3H), 7.78 (s, 1H), 7.71 ~ 7.60 (m, 9H), 6.57 (s, 1H), 1.88-1.82 (d, 12H), 0.35 (s, 9H), 7.30-7.12 (m, 8H), 6.83-6.65

MS/FAB: 842(M+)MS / FAB: 842 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.65(m, 1H), 8.56~8.52(m, 2H), 8.18~8.14(m, 3H), 7.78(s, 1H), 7.71~7.60(m, 6H), 7.30~7.25(m, 4H), 7.15~7.12(m, 2H), 7.00~6.90(s, 2H), 6.91~6.83(m, 3H), 6.73~6.71(m, 4H), 6.57(s, 1H), 1.88~1.82(d, 12H), 0.35(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.65 (m, 1H), 8.56 ~ 8.52 (m, 2H), 8.18 ~ 8.14 (m, 3H), 7.78 (s, 1H), 7.71 ~ 7.60 (m, 2H), 6.91-6.83 (m, 3H), 6.73-6.71 (m, 4H), 6.57 (m, s, 1H), 1.88-1.82 (d, 12H), 0.35 (s, 9H)

MS/FAB: 885(M+)MS / FAB: 885 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.65(m, 1H), 8.56~8.52(m, 2H), 8.18~8.14(m, 3H), 7.78(s, 1H), 7.71~7.60(m, 5H), 7.30~7.25(m, 4H), 7.15~7.12(m, 2H), 6.98~6.65(m, 11H), 6.57(s, 1H), 1.88~1.82(d, 12H), 0.35(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.65 (m, 1H), 8.56 ~ 8.52 (m, 2H), 8.18 ~ 8.14 (m, 3H), 7.78 (s, 1H), 7.71 ~ 7.60 (m, (S, 1H), 7.30-7.25 (m, 4H), 7.15-7.12 (m, 2H), 6.98-6.65 9H)

MS/FAB: 835(M+)MS / FAB: 835 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.18(d, 1H), 7.99(d, 1H), 7.78~7.76(m, 2H), 7.62~7.60(m, 2H), 7.48~7.12(m, 10H), 6.91~6.83(m, 3H), 6.73~6.65(m, 5H), 6.57(s, 1H), 6.49(d, 1H), 1.88~1.82(d, 12H), 0.35(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.18 (d, 1H), 7.99 (d, 1H), 7.78 ~ 7.76 (m, 2H), 7.62 ~ 7.60 (m, 2H) , 7.48-7.12 (m, 10H), 6.91-6.83 (m, 3H), 6.73-6.65 (m, 5H) , 0.35 (s, 9H)

MS/FAB: 781(M+)MS / FAB: 781 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.18(d, 1H), 7.78(s, 1H), 7.62~7.60(m, 2H), 7.47(d, 2H), 7.30(t, 4H), 7.15~7.12(m, 2H), 6.91~6.83(m, 4H), 6.73~6.65(m, 7H), 6.57(s, 1H), 1.88~1.82(d, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.18 (d, 1H), 7.78 (s, 1H), 7.62 ~ 7.60 (m, 2H), 7.47 (d, 2H), 7.30 (d, 12H), 7.18-7.12 (m, 2H), 6.91-6.83 (m, 4H), 6.73-6.65

MS/FAB: 687(M+)MS / FAB: 687 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.56(d, 1H), 8.18(d, 1H), 7.78(s, 1H), 7.62~7.60(m, 2H), 7.49(d, 2H), 7.30(t, 4H), 7.15~7.12(m, 2H), 6.91~6.83(m, 6H), 6.73(m, 4H), 6.65(d, 1H), 6.57(s, 1H), 1.88~1.82(d, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (d, 1H), 8.18 (d, 1H), 7.78 (s, 1H), 7.62 ~ 7.60 (m, 2H), 7.49 (d, 2H), 7.30 (t, 4H), 7.15-7.12 (m, 2H), 6.91-6.83 (m, 6H), 6.73 (m, 4H), 6.65 , 12H)

MS/FAB: 644(M+)MS / FAB: 644 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 4H), 6.95~6.89(m, 4H), 6.71~6.63(m, 4H), 6.45~6.51(m, 7H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 4H), 6.95 (S, 6H), 1.62 (s, 6H), 1.68 (s, 6H)

MS/FAB: 637(M+)MS / FAB: 637 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.18~7.10(m, 6H), 6.95~6.92(m, 2H), 6.81(m, 1H), 6.71~6.62(m, 5H), 6.53(m, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.18 ~ 7.10 (m, 6H) , 6.95 (m, 2H), 6.81 (m, 1H), 6.71-6.62 (m, 5H), 6.53 , ≪ / RTI > 6H), 1.62 (s, 6H)

MS/FAB: 644(M+)MS / FAB: 644 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.03(m, 5H), 6.95~6.84(m, 4H), 6.71~6.63(m, 4H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.03 (m, 5H) (S, 6H), 1.62 (s, 6H), 1.62 (s, 6H), 6.75-6.84 (m, 4H), 6.71-6.63

MS/FAB: 687(M+)MS / FAB: 687 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10~7.08(m, 5H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53~6.45(m, 7H), 6.37(s, 1H), 6.30(d, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.08 (m, 5H) 6H), 1.68 (s, 6H), 1.62 (m, 2H), 6.95-6.92 (m, 2H), 6.71-6.63 (s, 6 H)

MS/FAB: 637(M+)MS / FAB: 637 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 4H), 6.95 1H), 1.68 (s, 6H), 1.62 (s, 6H), 6.69 (d, )

MS/FAB: 624(M+)MS / FAB: 624 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 1H), 8.36~8.32(m, 2H), 7.98~7.94(m, 3H), 7.58(s, 1H), 7.51~7.40(m, 5H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.78~6.37(m, 13H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.36 ~ 8.32 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.58 (s, 1H), 7.51 ~ 7.40 (m, 6H), 1.62 (s, 6H), 7.60 (s, 6H)

MS/FAB: 763(M+)MS / FAB: 763 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36 (m, 1H), 7.99~7.94(m, 3H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.26(t, 1H), 7.17~7.10(m, 5H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.99 ~ 7.94 (m, 3H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.26 (t, 1H) , 7.17-7.10 (m, 5H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 4H), 6.53 (d, (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 620(M+)MS / FAB: 620 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(d, 3H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.40(m, 2H), 7.10(t, 4H), 6.95~6.89(m, 4H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 3H), 7.98 (m, 1H), 7.58 (s, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (t, 4H), 6.95 2H), 1.68 (s, 6H), 1.62 (s, 6H), 6.69 (d, )

MS/FAB: 620(M+)MS / FAB: 620 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.44~7.40(m, 9H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.71~6.53(m, 10H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (m, IH), 7.98 (m, IH), 7.58 (s, IH), 7.44-7.40 1H), 1.68 (s, 6H), 1.62 (s, 6H), 6.62 (s,

MS/FAB: 695(M+)MS / FAB: 695 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.77(m, 1H), 7.58(s, 1H), 7.52(d, 1H), 7.45~7.40(m, 3H), 7.28(m, 1H), 7.18~7.10(m, 5H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.77 (m, 1H), 7.58 (s, 1H), 7.52 (d, 1H), 7.45 ~ 7.40 (m, 3H), 7.28 (m, 1H), 7.18-7.10 (m, 5H), 6.95-6.92 (m, 2H), 6.71-6.63 (s, 1 H), 1.68 (s, 6 H), 1.62 (s, 12 H)

MS/FAB: 735(M+)MS / FAB: 735 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.31(m, 8H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.79~6.63(m, 6H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (m, IH), 7.98 (m, IH), 7.58 (s, IH), 7.42-7.31 6H), 1.62 (s, 6H), 1.62 (s, 6H), 6.62 (s,

MS/FAB: 695(M+)MS / FAB: 695 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98~7.92(m, 3H), 7.58(s, 1H), 7.47~7.40(m, 5H), 7.28(t, 1H), 7.10(t, 4H), 6.95~6.88(m, 3H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 ~ 7.92 (m, 3H), 7.58 (s, 1H), 7.47 ~ 7.40 (m, 5H), 7.28 (t, 1H) (D, 1H), 6.37 (s, 1H), 1.68 (s, 1H), 7.10 (t, 4H), 6.95-6.88 , ≪ / RTI > 6H), 1.62 (s, 6H)

MS/FAB: 669(M+)MS / FAB: 669 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.78~7.64(m, 4H), 7.58(s, 1H), 7.42~7.39(m, 4H), 7.26(t, 1H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (m, IH), 7.98 (m, IH), 7.78-7.64 , 7.26 (t, 1 H), 7.10 (t, 4H), 6.95-6.92 (m, 2H), 6.71-6.63 , 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 669(M+)MS / FAB: 669 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 1H), 8.36~8.32(m, 2H), 7.98~7.94(m, 3H), 7.58(s, 1H), 7.51~7.40(m, 5H), 7.10~7.07(m, 5H), 6.99~6.92(m, 3H), 6.71~6.53(m, 9H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.36 ~ 8.32 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.58 (s, 1H), 7.51 ~ 7.40 (m, (M, 3H), 6.71 (d, IH), 6.37 (s, IH), 1.68 , 1.62 (s, 6H)

MS/FAB: 770(M+)MS / FAB: 770 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 1H), 8.36~8.32(m, 2H), 7.98~7.94(m, 3H), 7.58(s, 1H), 7.51~7.40(m, 6H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.80~6.79(m, 2H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.36 ~ 8.32 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.58 (s, 1H), 7.51 ~ 7.40 (m, 2H), 6.71-6.63 (m, 4H), 6.53 (d, 4H), 6.45 (m, 2H), 6.95-6.92 , 6.37 (s, 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 813(M+)MS / FAB: 813 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.80(s, 1H), 8.40~8.36(m, 3H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.31(m, 22H), 6.96~6.92(m, 4H), 6.75(s, 4H), 6.63(s, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.80 (s, 1 H), 8.40-8.36 (m, 3H), 7.98 6H), 1.62 (s, 6H), 6.62 (s, 2H), 6.96 (s, )

MS/FAB: 925(M+)MS / FAB: 925 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 4H), 8.36~8.32(m, 5H), 7.98~7.94(m, 9H), 7.58~7.40(m, 15H), 7.10(t, 2H), 6.96~6.92(m, 4H), 6.75~6.63(m, 7H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 4H), 8.36 ~ 8.32 (m, 5H), 7.98 ~ 7.94 (m, 9H), 7.58 ~ 7.40 (m, 15H), 7.10 (t, 2H), 6.96-6.92 (m, 4H), 6.75-6.63 (m, 7H), 6.53 (d, 2H), 6.45 (s, 6 H)

MS/FAB: 1123(M+)MS / FAB: 1123 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98~7.82(m, 13H), 7.63~7.58(m, 5H), 7.49~7.42(m, 14H), 7.10(t, 2H), 6.96~6.92(m, 4H), 6.75~6.63(m, 7H), 6.53(m, 2H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 ~ 7.82 (m, 13H), 7.63 ~ 7.58 (m, 5H), 7.49 ~ 7.42 (m, 14H), 7.10 (t, 2H), 6.96-6.92 (m, 4H), 6.75-6.63 (m, 7H), 6.53 (m, 2H), 6.45 (s, 6 H)

MS/FAB: 1123(M+)MS / FAB: 1123 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 4H), 8.36~8.32(m, 5H), 7.98~7.94(m, 9H), 7.58(s, 1H), 7.51~7.40(m, 14H), 7.15~7.10(m, 18H), 6.96~6.92(m, 4H), 6.75~6.61(m, 5H), 6.63(m, 2H), 6.53(m, 2H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 4H), 8.36 ~ 8.32 (m, 5H), 7.98 ~ 7.94 (m, 9H), 7.58 (s, 1H), 7.51 ~ 7.40 (m, 2H), 6.53 (m, 2H), 6.45 (m, 1H), 7.15-7.10 (m, 18H), 6.96-6.92 , 6.37 (s, 1 H), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 1427(M+)MS / FAB: 1427 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98~7.82(m, 13H), 7.63~7.58(m, 5H), 7.49~7.40(m, 14H), 7.15~7.10(m, 18H), 6.96~6.92(m, 4H), 6.75~6.71(m, 5H), 6.63(m, 2H), 6.53(m, 2H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (m, 1H), 7.98-7.82 (m, 13H), 7.63-7.58 (m, 5H), 7.49-7.40 1H), 6.37 (s, 1H), 6.96-6.92 (m, 4H), 6.75-6.71 (m, , 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 1427(M+)MS / FAB: 1427 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58~7.56(m, 7H), 7.44~7.31(m, 26H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71(m, 1H), 6.63~6.59(m, 8H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 ~ 7.56 (m, 7H), 7.44 ~ 7.31 (m, 26H), 7.10 (t, 2H) , 6.95 (m, 2H), 6.71 (m, 1H), 6.63-6.59 (m, 8H) , 6H)

MS/FAB: 1075(M+)MS / FAB: 1075 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 4H), 8.36~8.32(m, 5H), 7.98~7.94(m, 9H), 7.58~7.45(m, 25H), 7.10(t, 2H), 6.95~6.92(m, 2H), 6.71~6.59(m, 9H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 4H), 8.36 ~ 8.32 (m, 5H), 7.98 ~ 7.94 (m, 9H), 7.58 ~ 7.45 (m, 25H), 7.10 (t, 2H), 6.95-6.92 (m, 2H), 6.71-6.59 (m, 9H), 6.45 (m,

MS/FAB: 1275(M+)MS / FAB: 1275 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58(s, 1H), 7.42~7.31(m, 12H), 7.10(t, 4H), 6.96~6.92(m, 3H), 6.75~6.71(m, 6H), 6.53(m, 4H), 6.45(m, 1H), 6.37(s, 1H), 1.68 1 H NMR (300 MHz, CDCl 3 ):? 8.36 (m, IH), 7.98 (m, IH), 7.58 (s, IH), 7.42-7.31 1H), 6.37 (s, 1H), 1.68 (m, 2H)

(s, 6H), 1.62(s, 6H)(s, 6 H), 1.62 (s, 6 H)

MS/FAB: 771(M+)MS / FAB: < / RTI & gt ; 771 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 2H), 8.36~8.32(m, 3H), 7.98~7.94(m, 5H), 7.58(s, 1H), 7.51~7.40(m, 8H), 7.10(t, 4H), 6.96~6.92(m, 3H), 6.75~6.63(m, 6H), 6.53(m, 4H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 2H), 8.36 ~ 8.32 (m, 3H), 7.98 ~ 7.94 (m, 5H), 7.58 (s, 1H), 7.51 ~ 7.40 (m, 6H), 6.53 (m, 4H), 6.45 (m, IH), 6.37 (s, IH), 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 871(M+)MS / FAB: 871 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98~7.82(m, 7H), 7.63~7.58(m, 3H), 7.49~7.40(m, 8H), 7.10(t, 4H), 6.96~6.92(m, 3H), 6.75~6.63(m, 6H), 6.53(m, 4H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 ~ 7.82 (m, 7H), 7.63 ~ 7.58 (m, 3H), 7.49 ~ 7.40 (m, 8H), 7.10 (t, 6H), 6.63 (s, 3H), 6.75 (m, 2H), 6.96 (m, (s, 6 H)

MS/FAB: 871(M+)MS / FAB: 871 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 2H), 8.36~8.32(m, 3H), 7.98~7.94(m, 5H), 7.58(s, 1H), 7.51~7.40(m, 8H), 7.15~7.10(m, 12H), 6.96~6.92(m, 3H), 6.75~6.63(m, 6H), 6.53(m, 4H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 2H), 8.36 ~ 8.32 (m, 3H), 7.98 ~ 7.94 (m, 5H), 7.58 (s, 1H), 7.51 ~ 7.40 (m, 6H), 6.53 (m, 4H), 6.45 (m, IH), 6.37 (s, IH), 7.17-7.10 (m, 12H), 6.96-6.92 , 1.68 (s, 6 H), 1.62 (s, 6 H)

MS/FAB: 1023(M+)MS / FAB: 1023 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98~7.82(m, 7H), 7.63~7.58(m, 3H), 7.49~7.40(m, 8H), 7.15~7.10(m, 12H), 6.96~6.92(m, 3H), 6.75~6.63(m, 6H), 6.53(m, 4H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 ~ 7.82 (m, 7H), 7.63 ~ 7.58 (m, 3H), 7.49 ~ 7.40 (m, 8H), 7.15 ~ 7.10 ( 6H), 6.53 (m, 4H), 6.45 (m, IH), 6.37 (s, IH), 1.68 (s, 6H) , 1.62 (s, 6H)

MS/FAB: 1023(M+)MS / FAB: 1023 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.36(m, 1H), 7.98(m, 1H), 7.58~7.56(m, 4H), 7.44~7.31(m, 14H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.71~6.53(m, 10H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.58 ~ 7.56 (m, 4H), 7.44 ~ 7.31 (m, 14H), 7.10 (t, 4H) 6H), 1.62 (s, 6H), 6.62 (s, 2H), 6.95-6.92 (m, 2H), 6.71-6.53

MS/FAB: 847(M+)MS / FAB: 847 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 2H), 8.36~8.32(m, 3H), 7.98~7.94(m, 5H), 7.58~7.44(m, 14H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.71~6.53(m, 10H), 6.45(m, 1H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 2H), 8.36 ~ 8.32 (m, 3H), 7.98 ~ 7.94 (m, 5H), 7.58 ~ 7.44 (m, 14H), 7.10 (t, (S, 6H), 1.62 (s, 6H), 1.62 (s, 6H), 6.70

MS/FAB: 947(M+)MS / FAB: 947 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.92~7.86(m, 4H), 7.76(s, 2H), 7.62~7.51(m, 11H), 7.37(t, 2H), 7.27~7.01(m, 6H), 6.80(t, 1H), 6.72~6.46(m, 10H), 1.67(s, 24H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.92 ~ 7.86 (m, 4H), 7.76 (s, 2H), 7.62 ~ 7.51 (m, 11H) , 7.37 (t, 2H), 7.27-7.01 (m, 6H), 6.80 (t,

MS/FAB: 1003(M+)MS / FAB: < / RTI & gt ; 1003 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.92~7.62(m, 5H), 7.54~7.51(m, 5H), 7.37(t, 1H), 7.27~7.01(m, 7H), 6.80~6.62(m, 10H), 6.54(d, 1H), 6.46(s, 1H), 1.67(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.92 ~ 7.62 (m, 5H), 7.54 ~ 7.51 (m, 5H), 7.37 (t, 1H) , 7.27-7.01 (m, 7H), 6.80-6.62 (m, 10H), 6.54

MS/FAB: 811(M+)MS / FAB: < / RTI & gt ; 811 (M + )

[합성예 185] 화합물 [185]의 합성[Synthesis Example 185] Synthesis of compound [185]

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H),8.07(d, 1H), 7.92~7.62(m, 17H), 7.54~7.37(m, 10H), 7.27~7.01(m, 10H), 6.84~6.72(m, 7H), 6.62(d, 2H), 6.54(d, 1H), 6.46(s, 1H), 1.67(s, 36H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (m, 10H), 7.27-7.01 (m, 2H), 6.54 (d, 1H), 6.46 (s, 1H), 1.67 (s, 36H)

MS/FAB: 1387(M+)MS / FAB: 1387 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.92~7.62(m, 9H), 7.54~7.49(m, 4H), 7.37(t, 2H), 7.27~7.01(m, 9H), 6.84~6.62(m, 10H), 6.54(d, 1H), 6.46(s, 1H), 1.67(s, 24H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.92 ~ 7.62 (m, 9H), 7.54 ~ 7.49 (m, 4H), 7.37 (t, 2H) , 7.27-7.01 (m, 9H), 6.84-6.62 (m, 10H), 6.54

MS/FAB: 1003(M+)MS / FAB: < / RTI & gt ; 1003 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.11~8.07(m, 3H), 7.87~7.81(m, 6H), 7.70~7.67(m, 9H), 7.51~7.49(m, 2H), 7.19(t, 2H), 7.04~7.01(m, 4H), 6.80~6.54(m, 6H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (m, 9H), 7.51-7.49 (m, 3H) 2H), 7.19 (t, 2H), 7.04-7.01 (m, 4H), 6.80-6.44 (m, 6H)

MS/FAB: 867(M+)MS / FAB: 867 (M < + & gt ; ) [

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.11~8.07(m, 3H), 7.87~7.44(m, 19H), 7.28~7.19(m, 3H) 7.04~6.72(m, 6H), 6.62~6.6.54(m, 3H), 6.46(s, 1H), 5.92(d, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.11 ~ 8.07 (m, 3H), 7.87 ~ 7.44 (m, 19H), 7.28 ~ 7.19 (m, 3H) 7.04 ~ 6.72 (m , 6H), 6.62-6.654 (m, 3H), 6.46 (s, IH), 5.92

MS/FAB: 908(M+)MS / FAB: 908 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.67(s, 1H), 7.51~7.04(m, 23H), 6.80~6.72(m, 6H), 6.62(d, 4H), 6.54~6.46(m, 4H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.67 (s, 1H), 7.51 ~ 7.04 (m, 23H), 6.80 ~ 6.72 (m, 6H) , 6.62 (d, 4H), 6.54-6.46 (m, 4H), 1.67 (s, 12H)

MS/FAB: 861(M+)MS / FAB: 861 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.67(s, 1H), 7.54~7.36(m, 17H), 7.20~7.01(m, 8H), 6.80~6.62(m, 10H), 6.54(d, 1H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.67 (s, 1H), 7.54 ~ 7.36 (m, 17H), 7.20 ~ 7.01 (m, 8H) , 6.50 (d, 1H), 6.67 (s, 1H), 1.67 (s, 12H)

MS/FAB: 877(M+)MS / FAB: 877 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07~8.03(m, 5H), 7.78~7.67(m, 15H), 7.51~7.19(m, 10H), 7.04~7.01(m, 4H), 6.80~6.54(m, 6H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (d, 1H), 8.07-8.03 (m, 5H), 7.78-7.67 (m, 15H), 7.51-7.19 m, 4H), 6.80-6.44 (m, 6H), 6.46 (s,

MS/FAB: 1019(M+)MS / FAB: < / RTI & gt ; 1019 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07~7.67(m, 11H), 7.53~7.40(m, 12H), 7.19(t, 2H), 7.04~7.01(m, 3H), 6.80~6.62(m, 7H), 6.54(d, 1H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 ~ 7.67 (m, 11H), 7.53 ~ 7.40 (m, 12H), 7.19 (t, 2H), 7.04 ~ 7.01 (m, 3H), 6.80-6.62 (m, 7H), 6.54 (d, 1H), 6.46

MS/FAB: 895(M+)MS / FAB: 895 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07~7.67(m, 11H), 7.51~7.40(m, 5H), 7.19(t, 4H), 7.04~7.01(m, 3H), 6.80~6.54(m, 9H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (d, 1H), 8.07-7.67 (m, 11H), 7.51-7.40 3H), 6.80-6.44 (m, 9H), 6.46 (s, 1H), 1.67

MS/FAB: 819(M+)MS / FAB: 819 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07~8.05(m, 3H), 7.85(d, 1H), 7.70~7.49(m, 7H), 7.19(t, 4H), 7.04~7.01(m, 3H), 6.80~6.54(m, 9H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 ~ 8.05 (m, 3H), 7.85 (d, 1H), 7.70 ~ 7.49 (m, 7H), 7.19 (t, 4H) , 7.04-7.01 (m, 3H), 6.80-6.44 (m, 9H), 6.46

MS/FAB: 767(M+)MS / FAB: 767 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07~8.05(m, 3H), 7.96(s, 1H), 7.70~7.67(m, 5H), 7.54~7.36(m, 17H), 7.20~7.01(m, 7H), 6.80~6.54(m, 8H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 ~ 8.05 (m, 3H), 7.96 (s, 1H), 7.70 ~ 7.67 (m, 5H), 7.54 ~ 7.36 (m, 1H), 1.67 (s, 12H), 6.80 (s, 1H)

MS/FAB: 1026(M+)MS / FAB: 1026 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07~7.80(m, 4H), 7.70~7.49(m, 7H), 7.19(t, 4H), 7.04~6.54(m, 12H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 ~ 7.80 (m, 4H), 7.70 ~ 7.49 (m, 7H), 7.19 (t, 4H), 7.04 ~ 6.54 (m, 12H), 6.46 (s, 1 H), 1.67 (s, 12 H)

MS/FAB: 810(M+)MS / FAB: 810 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07(d, 1H), 7.86~7.85(m, 2H), 7.70~7.49(m, 8H), 7.19(t, 4H), 7.04~7.01(m, 3H), 6.80~6.54(m, 9H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 (d, 1H), 7.86 ~ 7.85 (m, 2H), 7.70 ~ 7.49 (m, 8H), 7.19 (t, 4H) , 7.04-7.01 (m, 3H), 6.80-6.44 (m, 9H), 6.46

MS/FAB: 760(M+)MS / FAB: < / RTI & gt ; 760 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.07~7.86(m, 4H), 7.70~7.67(m, 5H), 7.51~7.49(m, 2H), 7.19(t, 4H), 7.04~7.01(m, 3H), 6.80~6.54(m, 9H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.07 ~ 7.86 (m, 4H), 7.70 ~ 7.67 (m, 5H), 7.51 ~ 7.49 (m, 2H), 7.19 (t, 4H), 7.04-7.01 (m, 3H), 6.80-6.44 (m, 9H)

MS/FAB: 824(M+)MS / FAB: 824 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.25(s, 2H), 8.07(d, 1H), 7.78~7.70(m, 21H), 7.51~7.40(m, 20H), 7.23~7.01(m, 6H), 6.80~6.54(m, 6H), 6.46(s, 1H), 1.67(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.25 (s, 2H), 8.07 (d, 1H), 7.78 ~ 7.70 (m, 21H), 7.51 ~ 7.40 (m, 20H) , 7.23-7.01 (m, 6H), 6.80-6.44 (m, 6H), 6.46 (s,

MS/FAB: 1323(M+)MS / FAB: 1323 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.45(m, 1H), 8.25(s, 1H), 8.07(m, 1H), 7.78~7.70(m, 11H), 7.51~7.40(m, 11H), 7.23~7.19(m, 5H), 7.04~7.01(m, 2H), 6.80~6.72(m, 4H), 6.62(m, 4H), 6.54(m, 1H), 6.47(s, 1H), 1.77~1.71(d, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (m, IH), 8.25 (s, IH), 8.07 , 7.23-7.19 (m, 5H), 7.04-7.01 (m, 2H), 6.80-6.72 (m, 4H), 6.62 ~ 1.71 (d, 12H)

MS/FAB: 971(M+)MS / FAB: < / RTI & gt ; 971 (M + )

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

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.19(m, 6H), 7.04~7.01(m, 2H), 6.80~6.72(m, 5H), 6.63~6.62(m, 7H), 6.54(m, 1H), 1.77(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.46 (m, IH), 8.04 (m, IH), 7.83 (M, 2H), 7.01 (m, 2H), 6.80-6.72 (m, 5H), 6.63-6.62

MS/FAB: 619(M+)MS / FAB: 619 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.19(m, 4H), 7.04~6.97(m, 4H), 6.80~6.72(m, 4H), 6.63~6.62(m, 5H), 6.54~6.50(m, 3H), 2.33(s, 3H), 1.77(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.46 (m, IH), 8.04 (m, IH), 7.83 3H), 2.77 (s, 3H), 1.77 (s, 12H), 6.97 (m,

MS/FAB: 633(M+)MS / FAB: 633 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.19(m, 4H), 7.04~7.00(m, 4H), 6.80~6.72(m, 4H), 6.63~6.62(m, 5H), 6.54(m, 3H), 1.77(s, 12H), 1.34(s, 9H) 1 H NMR (300 MHz, CDCl 3 ):? 8.46 (m, IH), 8.04 (m, IH), 7.83 2H), 1.34 (s, 9H), 7.00 (m, 4H), 6.80-6.72 (m, 4H), 6.63-6.62

MS/FAB: 675(M+)MS / FAB: 675 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.19~7.14(m, 6H), 7.04~7.01(m, 2H), 6.80~6.72(m, 4H), 6.63~6.54(m, 8H), 1.77(s, 12H), 0.24(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.46 (m, 1H), 8.04 (m, 1H), 7.83 (d, 1H), 7.48 ~ 7.47 (m, 2H), 7.19 ~ 7.14 (m, 6H) , 7.04-7.01 (m, 2H), 6.80-6.72 (m, 4H), 6.63-6.44 (m, 8H)

MS/FAB: 691(M+)MS / FAB: 691 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.38(m, 2H), 7.19(m, 4H), 7.04~7.01(m, 2H), 6.80~6.72(m, 6H), 6.63~6.62(m, 5H), 6.54(m, 1H), 1.77(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.46 (m, 1H), 8.04 (m, 1H), 7.83 (d, 1H), 7.48 ~ 7.47 (m, 2H), 7.38 (m, 2H), 7.19 (m, 4H), 7.04-7.01 (m, 2H), 6.80-6.72 (m, 6H), 6.63-6.62

MS/FAB: 644(M+)MS / FAB: 644 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.19(m, 4H), 7.04~6.98(m, 4H), 6.80~6.72(m, 4H), 6.63~6.54(m, 8H), 1.77(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.46 (m, IH), 8.04 (m, IH), 7.83 (M, 4H), 6.80-6.72 (m, 4H), 6.63-6.44 (m, 8H)

MS/FAB: 637(M+)MS / FAB: 637 (M < + & gt ; ).

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

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.36(m, 2H), 7.19(m, 4H), 7.04~7.01(m, 2H), 6.80~6.72(m, 4H), 6.63~6.54(m, 8H), 1.77(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.46 (m, 1H), 8.04 (m, 1H), 7.83 (d, 1H), 7.48 ~ 7.47 (m, 2H), 7.36 (m, 2H), 7.19 (m, 4H), 7.04-7.01 (m, 2H), 6.80-6.72 (m, 4H), 6.63-6.44 (m, 8H)

MS/FAB: 687(M+)MS / FAB: 687 (M < + & gt ; ).

[합성예 208] 화합물 [208]의 합성[Synthesis Example 208] Synthesis of Compound [208]

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.27~7.19(m, 6H), 7.04~7.01(m, 2H), 6.90(m, 1H), 6.80~6.71(m, 5H), 6.63~6.62(m, 5H), 6.54(m, 1H), 1.77(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.46 (m, 1H), 8.04 (m, 1H), 7.83 (d, 1H), 7.48 ~ 7.47 (m, 2H), 7.27 ~ 7.19 (m, 6H) , 7.04-7.11 (m, 2H), 6.90 (m, 1H), 6.80-6.71 (m, 5H), 6.63-6.62

MS/FAB: 644(M+)MS / FAB: 644 (M < + & gt ; ).

[합성예 209] 화합물 [209]의 합성[Synthesis Example 209] Synthesis of Compound [209]

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.19~7.17(m, 5H), 7.04~7.01(m, 2H), 6.80~6.72(m, 4H), 6.63~6.54(m, 8H), 6.39(m, 1H), 1.77(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.46 (m, 1H), 8.04 (m, 1H), 7.83 (d, 1H), 7.48 ~ 7.47 (m, 2H), 7.19 ~ 7.17 (m, 5H) , 7.04-7.01 (m, 2H), 6.80-6.72 (m, 4H), 6.63-6.44 (m, 8H)

MS/FAB: 637(M+)MS / FAB: 637 (M < + & gt ; ).

[합성예 210] 화합물 [210]의 합성[Synthesis Example 210] Synthesis of Compound [210]

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.48~7.47(m, 2H), 7.19~7.12(m, 5H), 7.04~6.93(m, 4H), 6.80~6.72(m, 4H), 6.63~6.62(m, 6H), 6.54(m, 1H), 1.77(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.46 (m, 1H), 8.04 (m, 1H), 7.83 (d, 1H), 7.48 ~ 7.47 (m, 2H), 7.19 ~ 7.12 (m, 5H) , 7.04-6.93 (m, 4H), 6.80-6.72 (m, 4H), 6.63-6.62 (m, 6H), 6.54

MS/FAB: 687(M+)MS / FAB: 687 (M < + & gt ; ).

[합성예 211] 화합물 [211]의 합성[Synthesis Example 211] Synthesis of compound [211]

1H NMR (300 MHz, CDCl3): δ 8.46(m, 1H), 8.04(m, 1H), 7.83(d, 1H), 7.51~7.40(m, 12H), 7.19(m, 4H), 7.05~7.01(m, 3H), 6.84~6.72(m, 6H), 6.63~6.62(m, 5H), 6.54(m, 1H), 1.77(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.46 (m, IH), 8.04 (m, IH), 7.83 1H), 1.77 (s, 12H), 7.01 (m, 3H), 6.84-6.72 (m, 6H), 6.63-6.62

MS/FAB: 771(M+)MS / FAB: < / RTI & gt ; 771 (M + )

[합성예212] 화합물 [212]의 합성[Synthesis Example 212] Synthesis of Compound [212]

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.37~8.35(m, 2H), 7.98~7.94(m, 3H), 7.74(m, 1H), 7.51~7.38(m, 5H), 7.10(m, 4H), 6.95~6.92(m, 2H), 6.78~6.53(m, 11H), 6.45~6.43(m, 2H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.37 ~ 8.35 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.74 (m, 1H), 7.51 ~ 7.38 (m, 2H), 1.68 (s, 12H), 6.80 (m, 2H)

MS/FAB: 762(M+)MS / FAB: 762 (M < + & gt ; ).

[합성예 213] 화합물 [213]의 합성[Synthesis Example 213] Synthesis of Compound [213]

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.37~8.32(m, 2H), 7.98~7.94(m, 3H), 7.74(m, 1H), 7.51~7.38(m, 5H), 7.10~7.07(m, 5H), 6.99~6.92(m, 3H), 6.71~6.53(m, 10H), 6.45(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.37 ~ 8.32 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.74 (m, 1H), 7.51 ~ 7.38 (m, 5H), 7.10-7.07 (m, 5H), 6.99-6.92 (m, 3H), 6.71-6.53

MS/FAB: 769(M+)MS / FAB: 769 (M < + & gt ; ).

[합성예 214] 화합물 [214]의 합성[Synthesis Example 214] Synthesis of Compound [214]

1H NMR (300 MHz, CDCl3):δ 8.45(m, 1H), 8.37~8.32(m, 2H), 7.98~7.94(m, 3H), 7.74(m, 1H), 7.51~7.38(m, 6H), 7.10(m, 4H), 6.99~6.92(m, 2H), 6.80~6.79(m, 2H), 6.71~6.63(m, 4H), 6.54~6.53(m, 5H), 6.45(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (m, 1H), 8.37 ~ 8.32 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.74 (m, 1H), 7.51 ~ 7.38 (m, 2H), 6.71-6.63 (m, 4H), 6.54-6.53 (m, 5H), 6.45 (m, 2H) 1H), 1.68 (s, 12H)

MS/FAB: 812(M+)MS / FAB: 812 (M < + & gt ; ).

[합성예 215] 화합물 [215]의 합성[Synthesis Example 215] Synthesis of Compound [215]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.79~7.74(m, 2H), 7.56(m, 1H), 7.39~7.38(m, 2H), 7.28~7.10(m, 7H), 6.97~6.92(m, 3H), 6.71~6.63(m, 4H), 6.54~6.53(m, 5H), 6.45(m, 1H), 6.29(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.79 ~ 7.74 (m, 2H), 7.56 (m, 1H), 7.39 ~ 7.38 (m, 2H) , 7.28-7.10 (m, 7H), 6.97-6.92 (m, 3H), 6.71-6.63 (m, 4H), 6.54-6.53 , 1.68 (s, 12H)

MS/FAB: 708(M+)MS / FAB: 708 (M < + & gt ; ).

[합성예 216] 화합물 [216]의 합성[Synthesis Example 216] Synthesis of Compound [216]

1H NMR (300 MHz, CDCl3):δ 8.37~8.35(m, 2H), 7.95(m, 1H), 7.88(m, 1H), 7.74~7.71(m, 2H), 7.42~7.38(m, 4H), 7.17~7.10(m, 5H), 6.95~6.92(m, 2H), 6.76~6.63(m, 5H), 6.54~6.53(m, 5H), 6.45(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.35 (m, 2H), 7.95 (m, 1H), 7.88 (m, 1H), 7.74 ~ 7.71 (m, 2H), 7.42 ~ 7.38 (m, (M, 2H), 6.76-6.63 (m, 5H), 6.54-6.53 (m, 5H), 6.45 12H)

MS/FAB: 724(M+)MS / FAB: 724 (M < + & gt ; ) [

[합성예 217] 화합물 [217]의 합성[Synthesis Example 217] Synthesis of Compound [217]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.74(m, 1H), 7.42~7.31(m, 10H), 7.13~7.10(m, 6H), 6.98~6.92(m, 4H), 6.71~6.63(m, 4H), 6.54~6.53(m, 5H), 6.45(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.74 (m, 1H), 7.42 ~ 7.31 (m, 10H), 7.13 ~ 7.10 (m, 6H) , 6.98-6.92 (m, 4H), 6.71-6.63 (m, 4H), 6.54-6.53 (m, 5H)

MS/FAB: 788(M+)MS / FAB: 788 (M < + & gt ; ).

[합성예 218] 화합물 [218]의 합성[Synthesis Example 218] Synthesis of compound [218]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.74(m, 1H), 7.42~7.31(m, 12H), 7.10(m, 4H), 6.98~6.92(m, 4H), 6.71~6.63(m, 5H), 6.54~6.53(m, 5H), 6.45(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3 ):? 8.37 (m, IH), 7.95 (m, IH), 7.74 1H), 1.68 (s, 12H), 6.90 (m, 2H)

MS/FAB: 771(M+)MS / FAB: < / RTI & gt ; 771 (M + )

[합성예 219] 화합물 [219]의 합성[Synthesis Example 219] Synthesis of compound [219]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 8.02(m, 1H), 7.95(m, 1H), 7.78~7.72(m, 4H), 7.61(s, 4H), 7.39~7.38(m, 2H), 7.10(m, 4H), 6.95~6.92(m, 3H), 6.71~6.63(m, 4H), 6.54~6.53(m, 5H), 6.45(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 8.02 (m, 1H), 7.95 (m, 1H), 7.78 ~ 7.72 (m, 4H), 7.61 (s, 4H), 7.39 (M, 2H), 7.10 (m, 4H), 6.95-6.92 (m, 3H), 6.71-6.63 (s, 12 H)

MS/FAB: 742(M+)MS / FAB: 742 (M < + & gt ; ).

[합성예 220] 화합물 [220]의 합성[Synthesis Example 220] Synthesis of Compound [220]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95~7.94(m, 2H), 7.84(m, 1H), 7.77~7.69(m, 4H), 7.61(s, 4H), 7.41~7.31(m, 5H), 7.10(m, 4H), 6.95~6.92(m, 3H), 6.71~6.63(m, 4H), 6.54~6.53(m, 5H), 6.45(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 ~ 7.94 (m, 2H), 7.84 (m, 1H), 7.77 ~ 7.69 (m, 4H), 7.61 (s, 4H) , 7.41-7.31 (m, 5H), 7.10 (m, 4H), 6.95-6.92 (m, 3H), 6.71-6.63 , 1.68 (s, 12H)

MS/FAB: 819(M+)MS / FAB: 819 (M < + & gt ; ).

[합성예 221] 화합물 [221]의 합성[Synthesis Example 221] Synthesis of Compound [221]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 8.02~7.95(m, 3H), 7.78~7.72(m, 7H), 7.61(s, 8H), 7.39~7.38(m, 2H), 7.10(m, 2H), 6.95~6.92(m, 4H), 6.71~6.63(m, 3H), 6.54~6.53(m, 3H), 6.45(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 8.02 ~ 7.95 (m, 3H), 7.78 ~ 7.72 (m, 7H), 7.61 (s, 8H), 7.39 ~ 7.38 (m, 2H), 7.10 (m, 2H), 6.95-6.92 (m, 4H), 6.71-6.63 (m, 3H), 6.54-6.53

MS/FAB: 867(M+)MS / FAB: 867 (M < + & gt ; ) [

[합성예 222] 화합물 [222]의 합성[Synthesis Example 222] Synthesis of Compound [222]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 8.16(s, 2H), 7.95(m, 1H), 7.69~7.61(m, 21H), 7.41~7.31(m, 20H), 7.14~7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.54~6.53(m, 3H), 6.45(m, 1H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 8.16 (s, 2H), 7.95 (m, 1H), 7.69 ~ 7.61 (m, 21H), 7.41 ~ 7.31 (m, 20H) , 7.14-7.10 (m, 4H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 3H), 6.54-6.53

MS/FAB: 1323(M+)MS / FAB: 1323 (M < + & gt ; ).

[합성예 223] 화합물 [223]의 합성[Synthesis Example 223] Synthesis of compound [223]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.56(d, 1H), 7.42~7.40(m, 2H), 7.10(m, 6H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53~6.45(m, 8H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.56 (d, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (m, 6H), 6.95 (S, 6H), 1.62 (s, 6H), 1.62 (s, 6H)

MS/FAB: 618(M+)MS / FAB: 618 (M < + & gt ; ).

[합성예 224] 화합물 [224]의 합성[Synthesis Example 224] Synthesis of compound [224]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.56(d, 1H), 7.42~7.40(m, 2H), 7.10(m, 4H), 6.95~6.88(m, 4H), 6.71~6.63(m, 3H), 6.53~6.37(m, 9H), 2.24(s, 3H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.56 (d, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (m, 4H), 6.95 6H), 1.62 (s, 6H), 1.68 (s, 3H), 2.68 (s, 3H)

MS/FAB: 632(M+)MS / FAB: 632 (M < + & gt ; ).

[합성예 225] 화합물 [225]의 합성[Synthesis Example 225] Synthesis of Compound [225]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.56(d, 1H), 7.42~7.40(m, 2H), 7.10(m, 4H), 6.95~6.91(m, 4H), 6.71~6.63(m, 3H), 6.53~6.45(m, 8H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 1.25(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.56 (d, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (m, 4H), 6.95 6H), 1.62 (s, 6H), 1.25 (s, 1H), 6.71 (s, , 9H)

MS/FAB: 674(M+)MS / FAB: 674 (M < + & gt ; ) [

[합성예 226] 화합물 [226]의 합성[Synthesis Example 226] Synthesis of Compound [226]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.56(d, 1H), 7.42~7.40(m, 2H), 7.10~7.05(m, 6H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53~6.45(m, 8H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.56 (d, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 ~ 7.05 (m, 6H) 6H), 1.62 (s, 6H), 0.15 (m, 2H), 6.95-6.92 (m, 2H), 6.71-6.63 (s, 9 H)

MS/FAB: 690(M+)MS / FAB: 690 (M < + & gt ; ).

[합성예 227] 화합물 [227]의 합성[Synthesis Example 227] Synthesis of compound [227]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.56(d, 1H), 7.42~7.40(m, 2H), 7.29(m, 2H), 7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.56 (d, 1H), 7.42 ~ 7.40 (m, 2H), 7.29 (m, 2H), 7.10 (m, 4H), 6.95-6.92 (m, 2H), 6.71-6.63 (m, 5H), 6.53-6.45 (m, 6H), 6.37 , 6H)

MS/FAB: 643(M+)MS / FAB: 643 (M < + & gt ; ).

[합성예 228] 화합물 [228]의 합성[Synthesis Example 228] Synthesis of compound [228]

1H NMR (300 MHz, CDCl3):δ 8.36(m, 1H), 7.98(m, 1H), 7.56(d, 1H), 7.42~7.40(m, 2H), 7.10(m, 4H), 6.95~6.89(m, 4H), 6.71~6.63(m, 3H), 6.53~6.45(m, 8H), 6.37(s, 1H), 1.68(s, 6H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (m, 1H), 7.98 (m, 1H), 7.56 (d, 1H), 7.42 ~ 7.40 (m, 2H), 7.10 (m, 4H), 6.95 (S, 6H), 1.62 (s, 6H), 1.62 (s, 6H)

MS/FAB: 636(M+)MS / FAB: 636 (M < + & gt ; ).

[합성예229] 화합물 [229]의 합성[Synthesis Example 229] Synthesis of Compound [229]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.18(m, 1H), 7.76(d, 1H), 7.62~7.60(m, 2H), 7.48(d, 2H), 7.30(t, 4H), 7.15~7.12(m, 2H), 6.91~6.83(m, 3H), 6.73~6.65(m, 8H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.18 (m, 1H), 7.76 (d, 1H), 7.62 ~ 7.60 (m, 2H), 7.48 (d, 2H), 7.30 (s, 1H), 1.88 (s, 6H), 1.82 (s, 1H), 7.17-7.12 (m, 2H), 6.91-6.83 , 6H)

MS/FAB: 686(M+)MS / FAB: 686 (M < + & gt ; ).

[합성예230] 화합물 [230]의 합성[Synthesis Example 230] Synthesis of Compound [230]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.18(m, 1H), 7.76(d, 1H), 7.62~7.60(m, 2H), 7.38~7.30(m, 6H), 7.15~7.12(m, 2H), 7.01(s, 1H), 6.91~6.82(m, 4H), 6.73~6.65(m, 6H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.18 (m, 1H), 7.76 (d, 1H), 7.62 ~ 7.60 (m, 2H), 7.38 ~ 7.30 (m, 6H) , 7.15 (s, 6H), 1.88 (s, 6H), 1.82 (m, 2H) (s, 6 H)

MS/FAB: 643(M+)MS / FAB: 643 (M < + & gt ; ).

[합성예231] 화합물 [231]의 합성[Synthesis Example 231] Synthesis of compound [231]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.18(m, 1H), 7.76(d, 1H), 7.62~7.60(m, 2H), 7.30~7.28(m, 5H), 7.15~7.12(m, 2H), 6.91~6.83(m, 3H), 6.73~6.65(m, 8H), 6.57(s, 1H), 6.50(d, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.18 (m, 1H), 7.76 (d, 1H), 7.62 ~ 7.60 (m, 2H), 7.30 ~ 7.28 (m, 5H) , 6.50 (d, IH), 1.88 (s, 6H), 1.82 (m, 2H), 7.15-7.12 (m, 2H), 6.91-6.83 (s, 6 H)

MS/FAB: 636(M+)MS / FAB: 636 (M < + & gt ; ).

[합성예232] 화합물 [232]의 합성[Preparation Example 232] Synthesis of Compound [232]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.18(m, 1H), 7.76(d, 1H), 7.62~7.60(m, 2H), 7.30~7.23(m, 5H), 7.15~7.04(m, 4H), 6.91~6.83(m, 3H), 6.73~6.65(m, 7H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.18 (m, 1H), 7.76 (d, 1H), 7.62 ~ 7.60 (m, 2H), 7.30 ~ 7.23 (m, 5H) , 7.15-7.04 (m, 4H), 6.91-6.83 (m, 3H), 6.73-6.65 (m, 7H), 6.57 (s,

MS/FAB: 686(M+)MS / FAB: 686 (M < + & gt ; ).

[합성예233] 화합물 [233]의 합성[Synthesis Example 233] Synthesis of compound [233]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.18(m, 1H), 7.76(d, 1H), 7.62~7.51(m, 12H), 7.30(t, 4H), 7.16~7.12(m, 3H), 6.95~6.83(m, 5H), 6.73~6.65(m, 6H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.56 (m, IH), 8.18 (m, IH), 7.76 (d, IH), 7.62-7.51 (S, 6H), 1.82 (s, 6H), 1.82 (s, 6H)

MS/FAB: 771(M+)MS / FAB: < / RTI & gt ; 771 (M + )

[합성예234] 화합물 [234]의 합성[Synthesis Example 234] Synthesis of compound [234]

1H NMR (300 MHz, CDCl3):δ 8.65(m, 1H), 8.56~8.52(m, 2H), 8.18~8.14(m, 3H), 7.76~7.60(m, 6H), 7.30(t, 4H), 7.15~7.12(m, 2H), 6.98~6.73(m, 13H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.65 (m, 1H), 8.56 ~ 8.52 (m, 2H), 8.18 ~ 8.14 (m, 3H), 7.76 ~ 7.60 (m, 6H), 7.30 (t, 2H), 6.98-6.73 (m, 13H), 1.88 (s, 6H), 1.82 (s, 6H)

MS/FAB: 762(M+)MS / FAB: 762 (M < + & gt ; ).

[합성예235] 화합물 [235]의 합성[Synthesis Example 235] Synthesis of compound [235]

1H NMR (300 MHz, CDCl3):δ 8.65(m, 1H), 8.56~8.52(m, 2H), 8.18~8.14(m, 3H), 7.76~7.60(m, 6H), 7.30~7.27(m, 5H), 7.19~7.12(m, 3H), 6.91~6.65(m, 10H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.65 (m, 1H), 8.56-8.52 (m, 2H), 8.18-8.14 (m, 3H), 7.76-7.60 (s, 6H), 1.82 (s, 6H), 1.82 (s, 6H), 7.19-7.12 (m, 3H), 6.91-6.65

MS/FAB: 769(M+)MS / FAB: 769 (M < + & gt ; ).

[합성예236] 화합물 [236]의 합성[Synthesis Example 236] Synthesis of Compound [236]

1H NMR (300 MHz, CDCl3):δ 8.65(m, 1H), 8.56~8.52(m, 2H), 8.18~8.14(m, 3H), 7.76~7.60(m, 7H), 7.30(t, 4H), 7.15~7.12(m, 2H), 7.00~6.99(m, 2H), 6.91~6.83(m, 3H), 6.73~6.65(m, 6H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.65 (m, 1H), 8.56 ~ 8.52 (m, 2H), 8.18 ~ 8.14 (m, 3H), 7.76 ~ 7.60 (m, 7H), 7.30 (t, (S, 1H), 1.88 (s, 1H), 7.15-7.12 (m, 2H), 7.00-6.99 (m, 2H), 6.91-6.83 6H), 1.82 (s, 6H)

MS/FAB: 812(M+)MS / FAB: 812 (M < + & gt ; ).

[합성예237] 화합물 [237]의 합성[Synthesis Example 237] Synthesis of compound [237]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.18(m, 1H), 7.99(m, 1H), 7.76(t, 2H), 7.62~7.60(m, 2H), 7.48~7.30(m, 7H), 7.17~7.12(m, 3H), 6.91~6.83(m, 3H), 6.73~6.65(m, 6H), 6.57(s, 1H), 6.49(d, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.18 (m, 1H), 7.99 (m, 1H), 7.76 (t, 2H), 7.62 ~ 7.60 (m, 2H), 7.48 1H), 6.49 (d, 1H), 1.88 (m, 3H), 7.71 (m, (s, 6 H), 1.82 (s, 6 H)

MS/FAB: 708(M+)MS / FAB: 708 (M < + & gt ; ).

[합성예238] 화합물 [238]의 합성[Synthesis Example 238] Synthesis of compound [238]

1H NMR (300 MHz, CDCl3):δ 8.56~8.55(m, 2H), 8.18(m, 1H), 8.08(s, 1H), 7.91(t, 1H), 7.76(d, 1H), 7.62~7.60(m, 4H), 7.37~7.30(m, 5H), 7.15~7.12(m, 2H), 6.96~6.83(m, 4H), 6.73~6.65(m, 6H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.56-8.55 (m, 2H), 8.18 (m, IH), 8.08 (s, IH), 7.91 2H), 6.96-6.83 (m, 4H), 6.73-6.65 (m, 6H), 6.57 (s, 1H) , 1.88 (s, 6 H), 1.82 (s, 6 H)

MS/FAB: 724(M+)MS / FAB: 724 (M < + & gt ; ) [

[합성예239] 화합물 [239]의 합성[Synthesis Example 239] Synthesis of compound [239]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.18(m, 1H), 7.76(d, 1H), 7.62~7.51(m, 10H), 7.33~7.30(m, 6H), 7.18~7.12(m, 4H), 6.91~6.83(m, 3H), 6.73~6.65(m, 6H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.18 (m, 1H), 7.76 (d, 1H), 7.62 ~ 7.51 (m, 10H), 7.33 ~ 7.30 (m, 6H) , 7.18-7.12 (m, 4H), 6.91-6.83 (m, 3H), 6.73-6.65 (m, 6H), 6.57 (s,

MS/FAB: 788(M+)MS / FAB: 788 (M < + & gt ; ).

[합성예240] 화합물 [240]의 합성[Synthesis Example 240] Synthesis of Compound [240]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.18(m, 1H), 7.76(d, 1H), 7.62~7.51(m, 12H), 7.30(t, 4H), 7.18~7.12(m, 4H), 6.91~6.83(m, 4H), 6.73~6.65(m, 6H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.56 (m, IH), 8.18 (m, IH), 7.76 (d, IH), 7.62-7.51 (S, 6H), 1.82 (s, 6H), 1.82 (s, 6H)

MS/FAB: 771(M+)MS / FAB: < / RTI & gt ; 771 (M + )

[합성예241] 화합물 [241]의 합성[Synthesis Example 241] Synthesis of Compound [241]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.22~8.18(m, 2H), 7.98~7.92(m, 3H), 7.81~7.76(m, 5H), 7.62~7.60(m, 2H), 7.30(t, 4H), 7.15~7.12(m, 3H), 6.91~6.83(m, 3H), 6.73~6.65(m, 6H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.22 ~ 8.18 (m, 2H), 7.98 ~ 7.92 (m, 3H), 7.81 ~ 7.76 (m, 5H), 7.62 ~ 7.60 ( 1H, m, 2H), 7.30 (t, 4H), 7.15-7.12 (m, 3H), 6.91-6.83 (m, 3H), 6.73-6.65 6H), 1.82 (s, 6H)

MS/FAB: 742(M+)MS / FAB: 742 (M < + & gt ; ).

[합성예242] 화합물 [242]의 합성[Synthesis Example 242] Synthesis of Compound [242]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.18~8.14(m, 2H), 8.04~7.97(m, 2H), 7.89(d, 2H), 7.81~7.76(m, 5H), 7.62~7.51(m, 5H), 7.30(t, 4H), 7.15~7.12(m, 3H), 6.91~6.83(m, 3H), 6.73~6.65(m, 6H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.18 ~ 8.14 (m, 2H), 8.04 ~ 7.97 (m, 2H), 7.89 (d, 2H), 7.81 ~ 7.76 (m, 5H), 7.62-7.51 (m, 5H), 7.30 (t, 4H), 7.15-7.12 (m, 3H), 6.91-6.83 (m, 3H), 6.73-6.65 1H), 1.88 (s, 6H), 1.82 (s, 6H)

MS/FAB: 819(M+)MS / FAB: 819 (M < + & gt ; ).

[합성예243] 화합물 [243]의 합성[Synthesis Example 243] Synthesis of compound [243]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.22~8.18(m, 3H), 7.98~7.92(m, 6H), 7.81~7.76(m, 9H), 7.62~7.60(m, 2H), 7.30(t, 2H), 7.18~7.12(m, 4H), 6.91~6.83(m, 2H), 6.73~6.65(m, 4H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.22 ~ 8.18 (m, 3H), 7.98 ~ 7.92 (m, 6H), 7.81 ~ 7.76 (m, 9H), 7.62 ~ 7.60 ( (m, 2H), 7.30 (t, 2H), 7.18-7.12 (m, 4H), 6.91-6.83 6H), 1.82 (s, 6H)

MS/FAB: 867(M+)MS / FAB: 867 (M < + & gt ; ) [

[합성예244] 화합물 [244]의 합성[Synthesis Example 244] Synthesis of Compound [244]

1H NMR (300 MHz, CDCl3):δ 8.56(m, 1H), 8.36(s, 2H), 8.18(m, 1H), 7.89~7.76(m, 21H), 7.62~7.51(m, 20H), 7.34~7.30(m, 4H), 7.15~7.12(m, 2H), 6.91~6.83(m, 2H), 6.73~6.65(m, 4H), 6.57(s, 1H), 1.88(s, 6H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.56 (m, 1H), 8.36 (s, 2H), 8.18 (m, 1H), 7.89 ~ 7.76 (m, 21H), 7.62 ~ 7.51 (m, 20H) 2H), 6.73-6.65 (m, 4H), 6.57 (s, 1H), 1.88 (s, 6H), 7.34-7.30 (m, 4H), 7.15-7.12 , 1.82 (s, 6 H)

MS/FAB: 1323(M+)MS / FAB: 1323 (M < + & gt ; ).

[합성예245] 화합물 [245]의 합성[Synthesis Example 245] Synthesis of compound [245]

1H NMR (300 MHz, CDCl3):δ 8.57(m, 1H), 8.15(m, 1H), 7.76(d, 1H), 7.59~7.58(m, 2H), 7.30(t, 4H), 7.15~7.12(m, 4H), 6.91~6.83(m, 4H), 6.73~6.65(m, 7H), 1.88(s, 12H), 1.82(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.57 (m, IH), 8.15 (m, IH), 7.76 (d, IH), 7.59-7.58 2H), 1.82 (s, 6H), 7.90 (m, 4H), 6.91-6.83 (m, 4H)

MS/FAB: 658(M+)MS / FAB: 658 (M < + & gt ; ).

[합성예246] 화합물 [246]의 합성[Synthesis Example 246] Synthesis of compound [246]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.56(d, 1H), 7.39~7.38(m, 2H), 6.95~6.88(m, 8H), 6.63(t, 2H), 6.45~6.41(m, 7H), 2.24(s, 6H), 1.68~1.62(d, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.56 (d, 1H), 7.39 ~ 7.38 (m, 2H), 6.95 ~ 6.88 (m, 8H) , 6.63 (t, 2H), 6.45-6.41 (m, 7H), 2.24 (s, 6H), 1.68-1.62

MS/FAB: 686.92(M+)MS / FAB: 686.92 (M < + & gt ; ).

[합성예247] 화합물 [247]의 합성[Synthesis Example 247] Synthesis of compound [247]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.56(d, 1H), 7.39~7.38(m, 2H), 6.95~6.91(m, 8H), 6.63(t, 2H), 6.46~6.45(m, 7H), 1.68(s, 12H), 1.62(s, 6H), 1.25(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.56 (d, 1H), 7.39 ~ 7.38 (m, 2H), 6.95 ~ 6.91 (m, 8H) , 6.63 (t, 2H), 6.46-6.45 (m, 7H), 1.68 (s, 12H)

MS/FAB: 771.08(M+)MS / FAB: 771.08 (M < + & gt ; ).

[합성예248] 화합물 [248]의 합성[Synthesis Example 248] Synthesis of compound [248]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.56(d, 1H), 7.39~7.38(m, 2H), 7.05(d, 4H), 6.95~6.92(m, 4H), 6.63(t, 2H), 6.51~6.41(m, 7H), 1.68(s, 12H), 1.62(s, 6H), 0.15(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.56 (d, 1H), 7.39 ~ 7.38 (m, 2H), 7.05 (d, 4H), 6.95 6H), 0.15 (s, 18H), 6.62 (s, 2H), 6.63 (m, 2H)

MS/FAB: 803.23(M+)MS / FAB: 803.23 (M < + & gt ; ).

[합성예249] 화합물 [249]의 합성[Synthesis Example 249] Synthesis of compound [249]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.56(d, 1H), 7.39~7.38(m, 2H), 7.29(d, 4H), 6.95~6.92(m, 4H), 6.71~6.63(m, 6H), 6.46~6.45(m, 3H), 1.68(s, 12H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.56 (d, 1H), 7.39 ~ 7.38 (m, 2H), 7.29 (d, 4H), 6.95 6H), 1.68 (s, 12H), 1.62 (s, 6H)

MS/FAB: 708.89(M+)MS / FAB: 708.89 (M < + & gt ; ).

[합성예250] 화합물 [250]의 합성[Synthesis Example 250] Synthesis of compound [250]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.56(d, 1H), 7.39~7.38(m, 2H), 6.95~6.89(m, 8H), 6.63(t, 2H), 6.51~6.45(m, 7H), 1.68~1.62(d, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.56 (d, 1H), 7.39 ~ 7.38 (m, 2H), 6.95 ~ 6.89 (m, 8H) , 6.63 (t, 2H), 6.51-6.45 (m, 7H), 1.68-1.62 (d, 18H)

MS/FAB: 694.85(M+)MS / FAB: 694.85 (M < + & gt ; ).

[합성예251] 화합물 [251]의 합성[Synthesis Example 251] Synthesis of Compound [251]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.56(d, 1H), 7.39~7.38(m, 2H), 7.27(d, 4H), 6.95~6.92(m, 4H), 6.63(t, 2H), 6.46~6.45(m, 7H), 1.68~1.62(d, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.56 (d, 1H), 7.39 ~ 7.38 (m, 2H), 7.27 (d, 4H), 6.95 2H), 6.46-6.45 (m, 7H), 1.68-1.62 (d, 18H)

MS/FAB: 795(M+)MS / FAB: 795 (M < + & gt ; ).

[합성예252] 화합물 [252]의 합성[Synthesis Example 252] Synthesis of Compound [252]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.56(d, 1H), 7.39~7.38(m, 2H), 7.18~7.17(m, 4H), 6.95~6.92(m, 4H), 6.81(m, 2H), 6.63~6.62(m, 4H), 6.46~6.45(m, 3H), 1.68~1.62(d, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.56 (d, 1H), 7.39 ~ 7.38 (m, 2H), 7.18 ~ 7.17 (m, 4H) 2H), 6.63-6.62 (m, 4H), 6.46-6.45 (m, 3H), 1.68-1.62 (m, 4H)

MS/FAB: 709(M+)MS / FAB: 709 (M < + & gt ; ).

[합성예253] 화합물 [253]의 합성[Synthesis Example 253] Synthesis of Compound [253]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.56(d, 1H), 7.39~7.38(m, 2H), 7.03~6.84(m, 10H), 6.63(t, 2H), 6.53~6.45(m, 5H), 1.68~1.62(d, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.56 (d, 1H), 7.39 ~ 7.38 (m, 2H), 7.03 ~ 6.84 (m, 10H) , 6.63 (t, 2H), 6.53-6.45 (m, 5H), 1.68-1.62 (d, 18H)

MS/FAB: 795(M+)MS / FAB: 795 (M < + & gt ; ).

[합성예254] 화합물 [254]의 합성[Synthesis Example 254] Synthesis of Compound [254]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.56(d, 1H), 7.39~7.38(m, 2H), 7.08(m, 2H), 6.95~6.92(m, 4H), 6.63(t, 2H), 6.50~6.45(m, 7H), 6.30(d, 2H), 1.68~1.62(d, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.56 (d, 1H), 7.39 ~ 7.38 (m, 2H), 7.08 (m, 2H), 6.95 2H), 6.30 (d, 2H), 1.68-1.62 (m, 4H), 6.63

MS/FAB: 695(M+)MS / FAB: 695 (M < + & gt ; ).

[합성예255] 화합물 [255]의 합성[Synthesis Example 255] Synthesis of compound [255]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 7.10(m, 4H), 6.95~6.92(m, 4H), 6.71~6.63(m, 5H), 6.53(d, 4H), 6.45(d, 2H), 1.68~1.62(d, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 7.10 (m, 4H), 6.95 2H), 1.68-1.62 (d, 18H), 6.92 (d, 2H)

MS/FAB: 659(M+)MS / FAB: 659 (M < + & gt ; ).

[합성예256] 화합물 [256]의 합성[Synthesis Example 256] Synthesis of compound [256]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 6.95~6.88(m, 8H), 6.63(t, 3H), 6.45~6.41(m, 6H), 2.24(s, 6H), 1.68~1.62(d, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 6.95 ~ 6.88 (m, 8H) , 6.63 (t, 3H), 6.45-6.41 (m, 6H), 2.24 (s, 6H), 1.68-1.62

MS/FAB: 687(M+)MS / FAB: 687 (M < + & gt ; ).

[합성예257] 화합물 [257]의 합성[Synthesis Example 257] Synthesis of Compound [257]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 6.95~6.91(m, 8H), 6.63(t, 3H), 6.45(d, 6H), 1.68(s, 12H), 1.62(s, 6H), 1.25(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 6.95 ~ 6.91 (m, 8H) 6H), 1.25 (s, 18H), 6.63 (s, 3H)

MS/FAB: 771(M+)MS / FAB: < / RTI & gt ; 771 (M + )

[합성예258] 화합물 [258]의 합성[Synthesis Example 258] Synthesis of compound [258]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 7.05(d, 4H), 6.95~6.92(m, 4H), 6.63(t, 3H), 6.51~6.45(m, 6H), 1.68(s, 12H), 1.62(s, 6H), 0.15(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 7.05 (d, 4H), 6.95 6H), 1.62 (s, 6H), 0.15 (s, 18H), 6.62 (s,

MS/FAB: 803(M+)MS / FAB: 803 (M < + & gt ; ).

[합성예259] 화합물 [259]의 합성[Synthesis Example 259] Synthesis of Compound [259]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 7.29(d, 4H), 6.95~6.92(m, 4H), 6.71~6.63(m, 7H), 6.45(d, 2H), 1.68~1.62(d, 18H), MS/FAB: 709(M+) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 7.29 (d, 4H), 6.95 MS / FAB: 709 (M + ), < RTI ID = 0.0 >

[합성예260] 화합물 [260]의 합성[Synthesis Example 260] Synthesis of Compound [260]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 6.95~6.89(m, 8H), 6.63(t, 3H), 6.51~6.45(m, 6H), 1.68~1.62(d, 18H), 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 6.95 ~ 6.89 (m, 8H) , 6.63 (t, 3H), 6.51-6.45 (m, 6H), 1.68-1.62 (d, 18H)

MS/FAB: 695(M+)MS / FAB: 695 (M < + & gt ; ).

[합성예261] 화합물 [261]의 합성[Synthesis Example 261] Synthesis of Compound [261]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 7.27(d, 4H), 6.95~6.92(m, 4H), 6.63(t, 3H), 6.46~6.45(m, 6H), 1.68~1.62(d, 18H), 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 7.27 (d, 4H), 6.95 , 6.63 (t, 3H), 6.46-6.45 (m, 6H), 1.68-1.62 (d, 18H)

MS/FAB: 795(M+)MS / FAB: 795 (M < + & gt ; ).

[합성예262] 화합물 [262]의 합성[Synthesis Example 262] Synthesis of Compound [262]

1H NMR (300 MHz, CDCl3):δ 8.37(m, 1H), 7.95(m, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 7.18~7.17(m, 4H), 6.95~6.92(m, 4H), 6.81(m, 2H), 6.63~6.62(m, 5H), 6.45(d, 2H), 1.68~1.62(d, 18H), 1 H NMR (300 MHz, CDCl 3): δ 8.37 (m, 1H), 7.95 (m, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 7.18 ~ 7.17 (m, 4H) , 6.95-6.92 (m, 4H), 6.81 (m, 2H), 6.63-6.62 (m, 5H)

MS/FAB: 709(M+)MS / FAB: 709 (M < + & gt ; ).

[합성예263] 화합물 [263]의 합성[Synthesis Example 263] Synthesis of compound [263]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 1H), 7.95(d, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 7.08(t, 2H), 6.95~6.92(m, 4H), 6.63(t, 3H), 6.50~6.45(m, 6H), 6.30(d, 2H), 1.68(s, 12H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 1H), 7.95 (d, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 7.08 (t, 2H), 6.95 2H), 1.68 (s, 6H), 1.62 (s, 6H), 6.63 (s,

MS/FAB: 695(M+)MS / FAB: 695 (M < + & gt ; ).

[합성예264] 화합물 [264]의 합성[Synthesis Example 264] Synthesis of compound [264]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 1H), 7.95(d, 1H), 7.58(s, 1H), 7.39~7.38(m, 2H), 7.03~6.84(m, 10H), 6.63(t, 3H), 6.43~6.45(m, 4H), 1.68(s, 12H), 1.62(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 1H), 7.95 (d, 1H), 7.58 (s, 1H), 7.39 ~ 7.38 (m, 2H), 7.03 ~ 6.84 (m, 10H) , 6.63 (t, 3H), 6.43-6.45 (m, 4H), 1.68

MS/FAB: 795(M+)MS / FAB: 795 (M < + & gt ; ).

[합성예265] 화합물 [265]의 합성[Synthesis Example 265] Synthesis of compound [265]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 6.53(t, 2H), 7.42~7.38(m, 4H), 7.10(t, 6H), 6.95~6.92(m, 2H), 6.71~6.63(m, 4H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 6.53 (t, 2H), 7.42 ~ 7.38 (m, 4H), 7.10 (t, 6H), 6.95 ~ 6.92 (m, 2H), 6.71-6.63 (m, 4H), 6.53-6.45 (m, 7H), 6.37 (s,

MS/FAB: 669(M+)MS / FAB: 669 (M < + & gt ; ).

[합성예266] 화합물 [266]의 합성[Synthesis Example 266] Synthesis of compound [266]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 6.53~6.41(m, 2H), 7.42~7.38(m, 4H), 7.10(t, 4H), 6.95~6.88(m, 4H), 6.71~6.63(m, 3H), 6.53~6.37(m, 8H), 2.24(s, 3H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 6.53 ~ 6.41 (m, 2H), 7.42 ~ 7.38 (m, 4H), 7.10 (t, 4H), 6.95 ~ 6.88 ( 3H), 1.74 (s, 6H), 1.68 (s, 6H), 6.74 (m, 2H)

MS/FAB: 683(M+)MS / FAB: 683 (M < + & gt ; ).

[합성예267] 화합물 [267]의 합성[Synthesis Example 267] Synthesis of Compound [267]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.38(m, 4H), 7.10(t, 4H), 6.95~6.91(m, 4H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H), 1.25(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.38 (m, 4H), 7.10 (t, 4H), 6.95 ~ 6.91 ( 6H), 1.25 (s, 6H), 1.25 (s, 9H), 6.71 (s,

MS/FAB: 725(M+)MS / FAB: 725 (M < + & gt ; ).

[합성예268] 화합물 [268]의 합성[Synthesis Example 268] Synthesis of Compound [268]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.38(m, 4H), 7.10~7.05(m, 6H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H), 0.15(s, 9H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.38 (m, 4H), 7.10 ~ 7.05 (m, 6H), 6.95 ~ 6H), 1.68 (s, 6H), 0.15 (s, 2H), 6.92 (m, 2H), 6.71-6.63 9H)

MS/FAB: 741(M+)MS / FAB: 741 (M < + & gt ; ).

[합성예269] 화합물 [269]의 합성[Synthesis Example 269] Synthesis of Compound [269]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.38(m, 4H), 7.29(d, 2H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 5H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.38 (m, 4H), 7.29 (d, 2H), 7.10 (t, (S, 6H), 1.68 (s, 6H), 1.67 (s, 6H), 6.71-6.92 (m, 2H)

MS/FAB: 694(M+)MS / FAB: 694 (M < + & gt ; ) [

[합성예270] 화합물 [270]의 합성[Synthesis Example 270] Synthesis of Compound [270]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.38(m, 4H), 7.10(t, 4H), 6.95~6.89(m, 4H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.38 (m, 4H), 7.10 (t, 4H), 6.95 ~ 6.89 ( (s, 6H), 1.68 (s, 6H), 1.68 (s, 3H)

MS/FAB: 687(M+)MS / FAB: 687 (M < + & gt ; ).

[합성예271] 화합물 [271]의 합성[Synthesis Example 271] Synthesis of Compound [271]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.38(m, 4H), 7.27(d, 2H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.38 (m, 4H), 7.27 (d, 2H), 7.10 (t, 1H), 1.74 (s, 6H), 1.68 (s, 6H), 6.71 (m, 2H)

MS/FAB: 737(M+)MS / FAB: 737 (M < + & gt ; ).

[합성예272] 화합물 [272]의 합성[Synthesis Example 272] Synthesis of Compound [272]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.38(m, 4H), 7.18~7.10(m, 6H), 6.95~6.92(m, 2H), 7.95~6.62(m, 5H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.38 (m, 4H), 7.18 ~ 7.10 (m, 6H), 6.95 ~ (S, 6H), 1.68 (s, 6H), 6.74 (s, 2H), 6.92 (m, 2H), 7.95-6.62

MS/FAB: 694(M+)MS / FAB: 694 (M < + & gt ; ) [

[합성예273] 화합물 [273]의 합성[Synthesis Example 273] Synthesis of compound [273]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.38(m, 4H), 7.10~7.08(m, 5H), 6.95~6.92(m, 2H), 6.71~6.63(m, 3H), 6.53~6.45(m, 7H), 6.37(s, 1H), 6.30(d, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.38 (m, 4H), 7.10 ~ 7.08 (m, 5H), 6.95 ~ 2H), 6.74 (s, 6H), 1.68 (s, 1H), 6.92 (m, 2H), 6.71-6.63 6H)

MS/FAB: 687(M+)MS / FAB: 687 (M < + & gt ; ).

[합성예274] 화합물 [274]의 합성[Synthesis Example 274] Synthesis of Compound [274]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.38(m, 4H), 7.10~6.84(m, 9H), 6.71~6.63(m, 3H), 6.53~6.45(m, 6H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.38 (m, 4H), 7.10 ~ 6.84 (m, 9H), 6.71 ~ 6H), 1.64 (s, 6H), 1.68 (s, 6H), 6.63 (s,

MS/FAB: 737(M+)MS / FAB: 737 (M < + & gt ; ).

[합성예 275] 화합물 [275]의 합성[Synthesis Example 275] Synthesis of Compound [275]

1H NMR (300 MHz, CDCl3): δ 8.36(d, 2H), 7.98~7.95(m, 2H), 7.42~7.31(m, 14H), 7.10(t, 4H), 6.96~6.92(m, 3H), 6.75~6.63(m, 5H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.36 (d, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.31 (m, 14H), 7.10 (t, 4H), 6.96 ~ 6.92 (m, 1H), 1.74 (s, 6H), 1.68 (s, 6H), 6.75 (d,

MS/FAB: 821(M+)MS / FAB: 821 (M < + & gt ; ).

[합성예 276] 화합물 [276]의 합성[Synthesis Example 276] Synthesis of Compound [276]

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.37~8.32(m, 3H), 7.98~7.94(m, 4H), 7.51~7.38(m, 7H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.78~6.37(m, 12H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (d, 1H), 8.37-8.32 (m, 3H), 7.98-7.94 (m, 4H), 7.51-7.38 (S, 6H), 1.68 (s, 6H), 1.68 (m, 2H)

MS/FAB: 813(M+)MS / FAB: 813 (M < + & gt ; ).

[합성예 277] 화합물 [277]의 합성[Synthesis Example 277] Synthesis of compound [277]

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.37~8.32(m, 3H), 7.98~7.94(m, 4H), 7.51~7.38(m, 7H), 7.10~7.07(m, 5H), 6.99~6.92(m, 3H), 6.71~6.45(m, 9H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.45 (d, 1H), 8.37-8.32 (m, 3H), 7.98-7.94 (m, 4H), 7.51-7.38 (s, 6H), 1.68 (s, 6H), 1.68 (s, 3H)

MS/FAB: 820(M+)MS / FAB: 820 (M < + & gt ; ) [

[합성예 278] 화합물 [278]의 합성[Synthesis Example 278] Synthesis of compound [278]

1H NMR (300 MHz, CDCl3): δ 8.45(d, 1H), 8.37~8.32(m, 3H), 7.98~7.94(m, 4H), 7.51~7.38(m, 8H), 7.10(t, 4H), 6.95~6.92(m, 2H), 6.80~6.89(m, 2H), 6.71~6.63(m, 3H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.45 (d, 1H), 8.37 ~ 8.32 (m, 3H), 7.98 ~ 7.94 (m, 4H), 7.51 ~ 7.38 (m, 8H), 7.10 (t, (S, 1H), 1.74 (s, 1H), 6.95-6.92 (m, 2H), 6.80-6.98 6H), 1.68 (s, 6H)

MS/FAB: 863(M+)MS / FAB: 863 (M < + & gt ; ).

[합성예 279] 화합물 [279]의 합성[Synthesis Example 279] Synthesis of Compound [279]

1H NMR (300 MHz, CDCl3): δ 8.37(d, 2H), 7.98~7.95(m, 2H), 7.79(d, 1H), 7.56(d, 1H), 7.42~7.38(m, 4H), 7.28~7.10(m, 7H), 6.97~6.92(m, 3H), 6.71~6.63(m, 3H), 6.53~6.45(m, 5H), 6.37(s, 1H), 6.29(d, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.98 ~ 7.95 (m, 2H), 7.79 (d, 1H), 7.56 (d, 1H), 7.42 ~ 7.38 (m, 4H) , 6.28 (d, IH), 7.28-7.10 (m, 7H), 6.97-6.92 (m, 3H), 6.71-6.63 , 1.74 (s, 6 H), 1.68 (s, 6 H)

MS/FAB: 758(M+)MS / FAB: 758 (M < + & gt ; ).

[합성예 280] 화합물 [280]의 합성[Synthesis Example 280] Synthesis of Compound [280]

1H NMR (300 MHz, CDCl3):δ 8.37~8.35(m, 3H), 7.95~7.88(m, 3H), 7.71(d, 1H), 7.42~7.38(m, 6H), 7.17~7.10(m, 5H), 6.95~6.92(m, 2H), 6.76~7.63(m, 4H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.37-8.35 (m, 3H), 7.95-7.88 (m, 3H), 7.71 1H), 1.74 (s, 6H), 1.68 (s, 2H), 6.75-6.92 (m, 2H) 6H)

MS/FAB: 775(M+)MS / FAB: 775 (M < + & gt ; ).

[합성예 281] 화합물 [281]의 합성[Synthesis Example 281] Synthesis of compound [281]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.31(m, 12H), 7.13~7.10(m, 6H), 6.98~6.92(m, 4H), 6.71~6.63(m, 3H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.31 (m, 12H), 7.13 ~ 7.10 (m, 6H), 6.98 ~ 1H), 1.74 (s, 6H), 1.68 (s, 6H), 6.74 (d,

MS/FAB: 839(M+)MS / FAB: < / RTI & gt ; 839 (M + )

[합성예 282] 화합물 [282]의 합성[Synthesis Example 282] Synthesis of compound [282]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.95(m, 2H), 7.42~7.31(m, 14H), 7.10(t, 4H), 6.98~6.92(m, 4H), 6.74~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 1H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.95 (m, 2H), 7.42 ~ 7.31 (m, 14H), 7.10 (t, 4H), 6.98 ~ 6.92 ( 1H), 1.74 (s, 6H), 1.68 (s, 6H), 6.74 (d,

MS/FAB: 821(M+)MS / FAB: 821 (M < + & gt ; ).

[합성예 283] 화합물 [283]의 합성[Synthesis Example 283] Synthesis of compound [283]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 8.02~7.95(m, 3H), 7.78~7.72(m, 3H), 7.61(d, 4H), 7.42~7.38(m, 4H), 7.10(t, 4H), 6.95~6.92(m, 3H), 6.71~6.63(m, 3H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.37-8.36 (m, 2H), 8.02-7.95 (m, 3H), 7.78-7.72 (m, 3H), 6.53-6.45 (m, 5H), 6.37 (s, IH), 1.74 (s, 6H), 1.68 (s, 6H)

MS/FAB: 793(M+)MS / FAB: 793 (M < + & gt ; ) [

[합성예 284] 화합물 [284]의 합성[Synthesis Example 284] Synthesis of compound [284]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 7.98~7.94(m, 3H), 7.84~7.77(m, 2H), 7.69(d, 2H), 7.61(d, 4H), 7.42~7.31(m, 7H), 7.10(t, 4H), 6.95~6.92(m, 3H), 6.71~6.63(m, 3H), 6.53~6.45(m, 5H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 7.98 ~ 7.94 (m, 3H), 7.84 ~ 7.77 (m, 2H), 7.69 (d, 2H), 7.61 (d, (M, 3H), 6.53-6.45 (m, 5H), 6.37 (s, 4H), 7.42-7.31 (m, 7H) 1H), 1.74 (s, 6H), 1.68 (s, 6H)

MS/FAB: 869(M+)MS / FAB: 869 (M < + & gt ; ).

[합성예 285] 화합물 [285]의 합성[Synthesis Example 285] Synthesis of compound [285]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 8.02~7.95(m, 4H), 7.78~7.72(m, 6H), 7.61(d, 8H), 7.42~7.38(m, 4H), 7.10(t, 2H), 6.95~6.92(m, 4H), 6.71~6.63(m, 2H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3 ):? 8.37-8.36 (m, 2H), 8.02-7.95 (m, 4H), 7.78-7.72 (m, 6H), 7.61 (d, 8H), 7.42-7.38 2H), 6.45 (d, IH), 6.37 (s, IH), 7.30 (m, 2H) , 1.74 (s, 6 H), 1.68 (s, 6 H)

MS/FAB: 917(M+)MS / FAB: 917 (M < + & gt ; ).

[합성예 286] 화합물 [286]의 합성[Synthesis Example 286] Synthesis of compound [286]

1H NMR (300 MHz, CDCl3):δ 8.37~8.36(m, 2H), 8.16(s, 1H), 7.98~7.95(m, 2H), 7.69~7.61(m, 20H), 7.42~7.31(m, 22H), 7.14~7.10(m, 4H), 6.95~6.92(m, 2H), 6.71~6.63(m, 2H), 6.53(d, 2H), 6.45(d, 1H), 6.37(s, 1H), 1.74(s, 6H), 1.68(s, 6H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 ~ 8.36 (m, 2H), 8.16 (s, 1H), 7.98 ~ 7.95 7.42 ~ 7.31 (m, 2H), 7.69 ~ 7.61 (m, 20H), ( 2H), 6.54 (d, 2H), 6.45 (d, 1H), 6.37 (s, 2H), 7.14-7.10 (m, 4H), 6.95-6.92 1H), 1.74 (s, 6H), 1.68 (s, 6H)

MS/FAB: 1373(M+)MS / FAB: 1373 (M < + & gt ; ).

[합성예 287] 화합물 [287]의 합성[Synthesis Example 287] Synthesis of compound [287]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 7.10(t, 4H), 6.95~6.92(m, 4H), 6.71~6.63(m, 4H), 6.53(d, 4H), 6.45(d, 2H), 1.74(s, 6H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 7.10 (t, 4H), 6.95 ~ 6.92 (m, 4H) , 6.71 (d, 2H), 1.74 (s, 6H), 1.68 (s, 12H)

MS/FAB: 708(M+)MS / FAB: 708 (M < + & gt ; ).

[합성예 288] 화합물 [288]의 합성[Synthesis Example 288] Synthesis of compound [288]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 6.95~6.88(m, 8H), 6.53(t, 2H), 6.45~6.41(m, 6H), 2.24(s, 6H), 1.74(s, 6H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 6.95 ~ 6.88 (m, 8H), 6.53 (t, 2H) , 6.45-6.41 (m, 6H), 2.24 (s, 6H), 1.74 (s, 6H)

MS/FAB: 736(M+)MS / FAB: 736 (M < + & gt ; ).

[합성예 289] 화합물 [289]의 합성[Synthesis Example 289] Synthesis of compound [289]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 6.95~6.91(m, 8H), 6.63(t, 2H), 6.45(d, 6H), 1.74(s, 6H), 1.68(s, 12H), 1.25(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 6.95 ~ 6.91 (m, 8H), 6.63 (t, 2H) , 6.45 (s, 6H), 1.74 (s, 6H), 1.68

MS/FAB: 821(M+)MS / FAB: 821 (M < + & gt ; ).

[합성예 290] 화합물 [290]의 합성[Synthesis Example 290] Synthesis of compound [290]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 7.05(d, 4H), 6.95~6.92(m, 4H), 6.63(t, 2H), 1.74(s, 6H), 1.68(s, 12H), 0.15(s, 18H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 7.05 (d, 4H), 6.95 ~ 6.92 (m, 4H) , 6.63 (s, 2H), 1.74 (s, 6H), 1.68

MS/FAB: 853(M+)MS / FAB: < / RTI & gt ; 853 (M + )

[합성예 291] 화합물 [291]의 합성[Synthesis Example 291] Synthesis of compound [291]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 7.29(d, 4H), 6.95~6.92(m, 4H), 6.71~6.63(m, 6H), 6.45(d, 2H), 1.74(s, 6H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 7.29 (d, 4H), 6.95 ~ 6.92 (m, 4H) , 6.71 (d, 2H), 1.74 (s, 6H), 1.68 (s, 12H)

MS/FAB: 758(M+)MS / FAB: 758 (M < + & gt ; ).

[합성예 292] 화합물 [292]의 합성[Synthesis Example 292] Synthesis of compound [292]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 6.95~6.89(m, 8H), 6.63(t, 2H), 6.51~6.45(m, 6H), 1.74(s, 6H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 6.95 ~ 6.89 (m, 8H), 6.63 (t, 2H) , 6.51-6.45 (m, 6H), 1.74 (s, 6H), 1.68 (s, 12H)

MS/FAB: 744(M+)MS / FAB: 744 (M < + & gt ; ).

[합성예 293] 화합물 [293]의 합성[Synthesis Example 293] Synthesis of compound [293]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 7.27(d, 4H), 6.95~6.92(m, 4H), 6.63(t, 2H), 6.46~6.45(m, 6H), 1.74(s, 6H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 7.27 (d, 4H), 6.95 ~ 6.92 (m, 4H) , 6.63 (t, 2H), 6.46-6.45 (m, 6H), 1.74 (s, 6H)

MS/FAB: 844(M+)MS / FAB: 844 (M < + & gt ; ).

[합성예 294] 화합물 [294]의 합성[Synthesis Example 294] Synthesis of compound [294]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 7.18~7.17(m, 4H), 6.95~6.92(m, 4H), 6.81(d, 2H), 6.63~6.62(m, 4H), 6.45(d, 2H), 1.74(s, 6H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 7.18 ~ 7.17 (m, 4H), 6.95 ~ 6.92 (m, 4H), 6.45 (d, 2H), 1.74 (s, 6H), 1.68 (s, 12H)

MS/FAB: 758(M+)MS / FAB: 758 (M < + & gt ; ).

[합성예 295] 화합물 [295]의 합성[Synthesis Example 295] Synthesis of compound [295]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 7.03~6.84(m, 10H), 6.63(t, 2H), 6.53(d, 2H), 6.45(d, 2H), 1.74(s, 6H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 7.03 ~ 6.84 (m, 10H), 6.63 (t, 2H) , 6.53 (d, 2H), 6.45 (d, 2H), 1.74 (s, 6H)

MS/FAB: 844(M+)MS / FAB: 844 (M < + & gt ; ).

[합성예 296] 화합물 [296]의 합성[Synthesis Example 296] Synthesis of compound [296]

1H NMR (300 MHz, CDCl3):δ 8.37(d, 2H), 7.95(d, 2H), 7.39~7.38(m, 4H), 7.08(t, 2H), 6.95~6.92(m, 4H), 6.63(t, 2H), 6.50~6.45(m, 6H), 6.30(d, 2H), 1.74(s, 6H), 1.68(s, 12H) 1 H NMR (300 MHz, CDCl 3): δ 8.37 (d, 2H), 7.95 (d, 2H), 7.39 ~ 7.38 (m, 4H), 7.08 (t, 2H), 6.95 ~ 6.92 (m, 4H) , 6.63 (t, 2H), 6.50-6.45 (m, 6H), 6.30 (d, 2H), 1.74

MS/FAB: 744(M+)MS / FAB: 744 (M < + & gt ; ).

본 발명의 화합물과 조합하여 사용할 수 있는 호스트 재료로는, 하기 (i) 내지 (xi)로 표시되는 화합물이 바람직하다:As the host material usable in combination with the compound of the present invention, the following compounds (i) to (xi) are preferred:

하기 화학식i로 표시되는 비대칭 안트라센:Asymmetric anthracene represented by the following formula (i):

[화학식 i](I)

Figure pat00029
Figure pat00029

상기 식에서, Ar은 치환되거나 비치환된 핵탄소수 10 내지 50의 축합 방향족기이다.In the above formula, Ar is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms.

Ar'는 치환되거나 비치환된 핵탄소수 6 내지 50의 방향족기이다.Ar 'is a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms.

X는 치환되거나 비치환된 핵탄소수 6 내지 50의 방향족기, 치환되거나 비치환된 핵원자수 5 내지 50의 방향족 복소환기, 치환되거나 비치환된 탄소수 1 내지 50의 알킬기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시기, 치환되거나 비치환된 탄소수 6 내지 50의 아르알킬기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴옥시기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴싸이오기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시카보닐기, 카복실기, 할로젠 원자, 사이아노기, 나이트로기, 하이드록실기이다.X is a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted carbon number Substituted or unsubstituted aralkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl groups having 6 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 50 nucleus atoms, A substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen atom, a cyano group, a nitro group, or a hydroxyl group.

a, b 및 c는 각각 0 내지 4의 정수이다.a, b, and c are each an integer of 0 to 4;

n은 1 내지 3의 정수이다. 또한, n이 2 이상인 경우, [ ] 안은 같거나 다를 수 있다.
n is an integer of 1 to 3; When n is 2 or more, the inside of [] may be the same or different.

하기 화학식 ii로 표시되는 비대칭 모노안트라센 유도체:An asymmetric monoanthracene derivative represented by the following formula (ii):

[화학식 ii](Ii)

Figure pat00030
Figure pat00030

상기 식에서, Ar1 및 Ar2는 각각 독립적으로, 치환되거나 비치환된 핵탄소수 6 내지 50의 방향족환기이고, m 및 n은 각각 1 내지 4의 정수이다. 단, m=n=1이고 또한 Ar1과 Ar2의 벤젠환에 대한 결합 위치가 좌우 대칭형인 경우에는, Ar1과 Ar2는 동일하지 않고, m 또는 n이 2 내지 4의 정수인 경우에는 m과 n은 다른 정수이다.Ar 1 and Ar 2 are each independently a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, and m and n are each an integer of 1 to 4. When m and n are integers of 2 to 4, m and n are different from each other when m = n = 1 and the bonding position of Ar1 and Ar2 to the benzene ring is symmetrical. It is an integer.

R1 내지 R10은, 각각 독립적으로, 수소 원자, 치환되거나 비치환된 핵탄소수 6 내지 50의 방향족환기, 치환되거나 비치환된 핵원자수 5 내지 50의 방향족 복소환기, 치환되거나 비치환된 탄소수 1 내지 50의 알킬기, 치환되거나 비치환된 사이클로알킬기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시기, 치환되거나 비치환된 탄소수 6 내지 50의 아르알킬기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴옥시기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴싸이오기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시카보닐기, 치환되거나 비치환된 실릴기, 카복실기, 할로젠 원자, 사이아노기, 나이트로기, 하이드록실기이다.
R1 to R10 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, An arylthio group having 5 to 50 ring atoms which are substituted or unsubstituted, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, An anion, a nitro group, and a hydroxyl group.

하기 화학식 iii으로 표시되는 비대칭 피렌 유도체:An asymmetric pyrene derivative represented by the following formula (iii):

[화학식 iii] (Iii)

Figure pat00031
Figure pat00031

상기 식에서, Ar 및 Ar'은, 각각 치환되거나 비치환된 핵탄소수 6 내지 50의 방향족기이다.In the above formulas, Ar and Ar 'are each a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms.

L 및 L'는, 각각 치환되거나 비치환된 페닐렌기, 치환되거나 비치환된 나프탈레닐렌기, 치환되거나 비치환된 플루오렌일렌기 또는 치환되거나 비치환된 다이벤조실롤릴렌기이다.L and L 'are each a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group or a substituted or unsubstituted dibenzylpolyhenylene group.

m은 0 내지 2의 정수, n은 1 내지 4의 정수, s는 0 내지 2의 정수, t는 0 내지 4의 정수이다.m is an integer of 0 to 2, n is an integer of 1 to 4, s is an integer of 0 to 2, and t is an integer of 0 to 4.

또한, L 또는 Ar은 피렌의 1 내지 5위 중 어느 하나에 결합하고, L' 또는 Ar'는 피렌의 6 내지 10위 중 어느 하나에 결합한다.L or Ar is bonded to any one of the first to fifth pyrene units, and L 'or Ar' is bonded to any one of 6 to 10 of the pyrene units.

단, n+t가 짝수일 때, Ar, Ar', L, L'는 하기 (1) 또는 (2)를 만족한다.However, when n + t is an even number, Ar, Ar ', L and L' satisfy the following (1) or (2).

(1) Ar≠Ar' 및/또는 L≠L'(여기서 ≠는, 다른 구조의 기인 것을 나타냄)(1) Ar? Ar 'and / or L? L' (wherein? Is a group of another structure)

(2) Ar=Ar'이고 L=L'일 때(2) when Ar = Ar 'and L = L'

(2-1) m≠s 및/또는 n≠t, 또는(2-1) m? S and / or n? T, or

(2-2) m=s이고 n=t일 때,(2-2) When m = s and n = t,

(2-2-1) L 및 L', 또는 피렌이, 각각 Ar 및 Ar' 상의 다른 결합 위치에 결합해 있거나, (2-2-1) L and L ', or pyrene bonded at different bonding positions on Ar and Ar', respectively,

(2-2-2) L 및 L', 또는 피렌이, Ar 및 Ar' 상의 같은 결합 위치에서 결합하고 있는 경우, L 및 L' 또는 Ar 및 Ar'의 피렌에 있어서의 치환 위치가 1위와 6위, 또는 2위와 7위인 경우는 없다.
(2-2-2) When L and L 'or pyrene is bonded at the same bonding position on Ar and Ar', the substitution positions of L and L 'or Ar and Ar' in the pyrene are 1 and 6 , Or the second and seventh places.

하기 화학식 iv로 표시되는 비대칭 안트라센 유도체.An asymmetric anthracene derivative represented by the following formula (iv).

[화학식 iv](Iv)

Figure pat00032
Figure pat00032

상기 식에서, A1 및 A2는, 각각 독립적으로, 치환되거나 비치환된 핵탄소수 10 내지 20의 축합 방향족환기이다. In the above formula, A1 and A2 are each independently a substituted or unsubstituted condensed aromatic ring group having 10 to 20 nuclear carbon atoms.

Ar1 및 Ar2는, 각각 독립적으로, 수소 원자 또는 치환되거나 비치환된 핵탄소수 6 내지 50의 방향족환기이다.Ar 1 and Ar 2 are each independently a hydrogen atom or a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms.

R1 내지 R10은, 각각 독립적으로, 수소 원자, 치환되거나 비치환된 핵탄소수 6 내지 50의 방향족환기, 치환되거나 비치환된 핵원자수 5 내지 50의 방향족 복소환기, 치환되거나 비치환된 탄소수 1 내지 50의 알킬기, 치환되거나 비치환된 사이클로알킬기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시기, 치환되거나 비치환된 탄소수 6 내지 50의 아르알킬기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴옥시기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴싸이오기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시카보닐기, 치환되거나 비치환된 실릴기, 카복실기, 할로젠 원자, 사이아노기, 나이트로기 또는 하이드록실기이다.R1 to R10 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, An arylthio group having 5 to 50 ring atoms which are substituted or unsubstituted, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, An amino group, an amino group, an amino group, a nitro group or a hydroxyl group.

Ar1, Ar2, R9 및 R10은, 각각 복수일 수도 있고, 인접하는 것끼리 포화 또는 불포화 환상 구조를 형성하고 있을 수도 있다.Each of Ar1, Ar2, R9 and R10 may be plural or adjacent to each other may form a saturated or unsaturated cyclic structure.

단, 화학식 1에 있어서, 중심의 안트라센의 9위 및 10위에, 상기 안트라센 상에 나타내는 X-Y축에 대하여 대칭형이 되는 기가 결합하는 경우는 없다.
However, in the formula (1), groups which are symmetrical with respect to the XY axis shown in the anthracene phase are not bonded at the 9th and 10th positions of the central anthracene.

하기 화학식 v로 표시되는 안트라센 유도체:An anthracene derivative represented by the following formula (v):

[화학식 v](V)

Figure pat00033
Figure pat00033

상기 식에서, R1 내지 R10은, 각각 독립적으로 수소 원자, 알킬기, 사이클로알킬기, 치환될 수 있는 아릴기, 알콕실기, 아릴옥시기, 알킬아미노기, 알켄일기, 아릴아미노기 또는 치환될 수 있는 복소환식기를 나타내고, a 및 b는 각각 1 내지 5의 정수를 나타내고, 그들이 2 이상인 경우, R1끼리 또는 R2끼리는 각각에 있어서 같거나 다를수 있고, 또한 R1끼리 또는 R2끼리가 결합하여 환을 형성하고 있을 수도 있고, R3과 R4, R5와 R6, R7과 R8, R9와R10이 서로 결합하여 환을 형성하고 있을 수도 있다. L1은 단일 결합, -O-, -S-, -N(R)-(R은 알킬기 또는 치환될 수 있는 아릴기임), 알킬렌기 또는 아릴렌기를 나타낸다.
Wherein R1 to R10 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group which may be substituted, an alkoxyl group, an aryloxy group, an alkylamino group, an alkenyl group, an arylamino group or an optionally substituted heterocyclic group And a and b each represent an integer of 1 to 5, and when they are two or more, R 1 or R 2 may be the same or different in each case, and R 1 or R 2 may combine to form a ring, R3 and R4, R5 and R6, R7 and R8, and R9 and R10 may be bonded to each other to form a ring. L1 represents a single bond, -O-, -S-, -N (R) - (R is an alkyl group or an aryl group which may be substituted), an alkylene group or an arylene group.

하기 화학식 vi으로 표시되는 안트라센 유도체:An anthracene derivative represented by the following formula (vi)

[화학식 vi][Formula (vi)

Figure pat00034
Figure pat00034

상기 식에서, R11 내지 R20은, 각각 독립적으로 수소 원자, 알킬기, 사이클로알킬기, 아릴기, 알콕실기, 아릴옥시기, 알킬아미노기, 아릴아미노기 또는 치환될 수 있는 복소환식기를 나타내고, c, d, e 및 f는 각각 1 내지 5의 정수를 나타내고, 그들이 2 이상인 경우, R11끼리, R12끼리, R16끼리 또는 R17끼리는, 각각에 있어서 같거나 다를 수 있고, 또한 R11끼리, R12끼리, R16끼리 또는 R17끼리가 결합하여 환을 형성하고 있을 수도 있고, R13과 R14, R18과 R19가 서로 결합하여 환을 형성하고 있을 수도 있다. L2는 단일 결합, -O-, -S-, -N(R)-(R은 알킬기 또는 치환될 수 있는 아릴기임), 알킬렌기 또는 아릴렌기를 나타낸다.
R11 to R20 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxyl group, an aryloxy group, an alkylamino group, an arylamino group or an optionally substituted heterocyclic group, and c, d, e And f each represent an integer of 1 to 5, and when they are two or more, R11, R12, R16 or R17 may be the same or different, and R11, R12, R16 or R17 May form a ring, or R13 and R14, or R18 and R19 may be bonded to each other to form a ring. L2 represents a single bond, -O-, -S-, -N (R) - (R represents an alkyl group or an aryl group which may be substituted), an alkylene group or an arylene group.

하기 화학식 vii로 표시되는 스파이로플루오렌 유도체;A spirofluorene derivative represented by the following formula (vii);

[화학식 vii][Formula vii]

Figure pat00035
Figure pat00035

상기 식에서, A5내지 A8은, 각각 독립적으로, 치환되거나 비치환된 바이페닐릴기 또는 치환되거나 비치환된 나프틸기이다.
In the above formulas, A5 to A8 are each independently a substituted or unsubstituted biphenylyl group or a substituted or unsubstituted naphthyl group.

하기 화학식 viii로 표시되는 축합환 함유 화합물.A condensed ring-containing compound represented by the following formula (viii).

[화학식 viii][Formula viii]

Figure pat00036
Figure pat00036

상기 식에서, A9 내지 A14는 상기와 같고, R21 내지 R23은, 각각 독립적으로, 수소 원자, 탄소수 1 내지 6의 알킬기, 탄소수 3 내지 6의 사이클로알킬기, 탄소수 1 내지 6의 알콕실기, 탄소수 5 내지 18의 아릴옥시기, 탄소수 7 내지 18의 아르알킬옥시기, 탄소수 5 내지 16의 아릴아미노기, 나이트로기, 사이아노기, 탄소수 1 내지 6의 에스터기 또는 할로젠 원자를 나타내고, A9내지 A14중 적어도 하나는 3환 이상의 축합 방향족환을 갖는 기이다.
A9 to A14 are as defined above and R21 to R23 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, an alkyl group having 5 to 18 carbon atoms An aryloxy group having 7 to 18 carbon atoms, an arylamino group having 5 to 16 carbon atoms, a nitro group, a cyano group, an ester group having 1 to 6 carbon atoms or a halogen atom, and at least one of A9 to A14 One is a group having three or more ring condensed aromatic rings.

하기 화학식 ix로 표시되는 플루오렌 화합물:A fluorene compound represented by the following formula (ix):

[화학식 [Chemical Formula ixix ]]

Figure pat00037
Figure pat00037

상기 식에서, R1 및 R2는, 수소 원자, 치환되거나 비치환된 알킬기, 치환 또는 비치환된 아르알킬기, 치환되거나 비치환된 아릴기, 치환되거나 비치환된 복소환기, 치환 아미노기, 사이아노기 또는 할로젠 원자를 나타낸다.Wherein R 1 and R 2 are selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, Atoms.

다른 플루오렌기에 결합하는 R1끼리, R2끼리는 같거나 다를 수 있고, 같은 플루오렌기에 결합하는 R1 및 R2는 같거나 다를 수 있다. R3 및 R4는, 수소 원자, 치환되거나 비치환된 알킬기, 치환되거나 비치환된 아르알킬기, 치환되거나 비치환된 아릴기 또는 치환되거나 비치환된 복소환기를 나타내고, 다른 플루오렌기에 결합하는 R3끼리, R4끼리는 같거나 다를 수 있고, 같은 플루오렌기에 결합하는 R3 및 R4는 같거나 다를 수 있다. Ar1 및 Ar2는, 벤젠환의 합계가 3개 이상인 치환되거나 비치환된 축합 다환 방향족기 또는 벤젠환과 복소환의 합계가 3개 이상인 치환되거나 비치환된 탄소로 플루오렌기에 결합하는 축합 다환 복소환기를 나타내고, Ar1 및 Ar2는 같거나 다를 수 있다. n은 1 내지 1O의 정수를 나타낸다.
R 1 and R 2 which are bonded to different fluorene groups may be the same or different, and R 1 and R 2 bonded to the same fluorene group may be the same or different. R3 and R4 represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, and R3 bonded to other fluorene groups, R4 may be the same or different, and R3 and R4 which are bonded to the same fluorene group may be the same or different. Ar 1 and Ar 2 represent a substituted or unsubstituted condensed polycyclic aromatic group having a total of three or more benzene rings or a condensed polycyclic heterocyclic group bonded to a fluorene group through a substituted or unsubstituted carbon having a total of three or more benzene and heterocyclic rings , Ar1 and Ar2 may be the same or different. n represents an integer of 1 to 10;

하기 화학식 x으로 표시되는 안트라센 중심 골격을 갖는 화합물:A compound having an anthracene center skeleton represented by the following formula (x):

[화학식 x][Formula x]

Figure pat00038
Figure pat00038

화학식 x에서, A1 및 A2는, 각각 독립적으로, 치환되거나 비치환된 핵탄소수 6 내지 20의 방향족환으로부터 유도되는 기이다. 상기 방향족환은 1 또는 2 이상의 치환기로 치환되어 있을 수도 있다.In the formula (X), A1 and A2 are each independently a group derived from a substituted or unsubstituted aromatic ring having 6 to 20 nuclear carbon atoms. The aromatic ring may be substituted with one or two or more substituents.

상기 치환기는, 치환되거나 비치환된 핵탄소수 6 내지 50의 아릴기, 치환되거나 비치환된 탄소수 1 내지 50의 알킬기, 치환되거나 비치환된 탄소수 3 내지 50의 사이클로알킬기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시기, 치환되거나 비치환된 탄소수 6 내지 50의 아르알킬기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴옥시기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴싸이오기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시카보닐기, 치환되거나 비치환된 실릴기, 카복실기, 할로젠 원자, 사이아노기, 나이트로기 및 하이드록실기로부터 선택된다.The substituted group is preferably a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, A substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, an arylthio group having 5 to 50 substituted or unsubstituted nuclei, , A substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group and a hydroxyl group.

상기 방향족환이 2 이상의 치환기로 치환되어 있는 경우, 상기 치환기는 같거나 다를 수 있고, 인접하는 치환기끼리는 서로 결합하여 포화 또는 불포화 환상 구조를 형성하고 있을 수도 있다.When the aromatic ring is substituted with at least two substituents, the substituents may be the same or different, and adjacent substituents may be bonded to each other to form a saturated or unsaturated cyclic structure.

R1 내지 R8은, 각각 독립적으로, 수소 원자, 치환되거나 비치환된 핵탄소수 6 내지 50의 아릴기, 치환되거나 비치환된 핵원자수 5 내지 50의 헤테로아릴기, 치환되거나 비치환된 탄소수 1 내지 50의 알킬기, 치환되거나 비치환된 탄소수 3 내지 50의 사이클로알킬기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시기, 치환되거나 비치환된 탄소수 6 내지 50의 아르알킬기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴옥시기, 치환되거나 비치환된 핵원자수 5 내지 50의 아릴싸이오기, 치환되거나 비치환된 탄소수 1 내지 50의 알콕시카보닐기, 치환되거나 비치환된 실릴기, 카복실기, 할로젠 원자, 사이아노기, 나이트로기 및 하이드록실기로부터 선택된다.
Each of R1 to R8 independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 nuclear atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, An arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a substituted or unsubstituted arylthio group, A halogen atom, a cyano group, a nitro group and a hydroxyl group.

상기 화학식 x에서 A1과 A2가 다른 기인 하기 화학식 xi로 표시되는 구조를 갖는 화합물:A compound having a structure represented by the following formula (xi) wherein A1 and A2 are different groups in the above formula (x):

[화학식 xi](Xi)

Figure pat00039
Figure pat00039

화학식 xi에서, A1 및 A2, R1 내지 R8은, 각각 독립적으로, 화학식 x과 같다.In formula (xi), A1 and A2, and R1 to R8 are each independently the same as in formula (x).

단, 중심의 안트라센의 9위 및 10위에, 상기 안트라센 상에 나타내는 X-Y축에 대하여 대칭형이 되는 기가 결합하는 경우는 없다.
However, the groups which are symmetrical with respect to the XY axis shown in the anthracene phase are not bonded to the ninth and tenth positions of the central anthracene.

이상의 호스트 재료 중에서도, 바람직한 것은 안트라센 유도체, 더 바람직한 것은 모노안트라센 유도체, 특히 바람직한 것은 비대칭 안트라센이다.Among the host materials described above, preferred is an anthracene derivative, more preferably a monoanthracene derivative, and particularly preferably an asymmetric anthracene.

이하에서, 실시예를 통하여 본 발명을 보다 상세히 설명한다. 그러나, 하기의 실시예는 본 발명을 더욱 구체적으로 설명하기 위한 것으로서, 본 발명의 범위가 하기의 실시예에 의하여 한정되는 것은 아니다. 하기의 실시예는 본 발명의 범위 내에서 당업자에 의해 적절히 수정, 변경될 수 있다.
Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples are intended to further illustrate the present invention, and the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

비교예 1.Comparative Example 1

하기 화학식 a로 표시되는 화합물 a를 형광 청색 호스트로 사용하고, 하기 화학식 b로 표시되는 화합물 b를 형광 청색 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 유기전기발광소자를 제작하였다: ITO/2-TNATA(80nm)/α-NPD(30nm)/화합물a+화합물b(30nm)/Alq3(30nm)/LiF(0.5nm)/ Al(60nm).A compound represented by the following formula (a) is used as a fluorescent blue host, and a compound b represented by the following formula (b) is used as a fluorescent blue dopant, and 2-TNATA (4,4 ' 2-yl) -N-phenylamino) -triphenylamine was used as a hole injection layer material and α-NPD (N, N'-di (naphthalene- (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) was used as an organic electroluminescent device having the following structure: ITO / 2-TNATA (80 nm) /? -NPD 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 순수한 물 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 b로 표시되는 화합물 b(5% 도핑)를 진공 증착하여 30nm 두께의 발광층을 형성하였다. 이후, 상기 발광층 상부에 Alq3 화합물을 30nm의 두께로 진공증착하여 전자수송층을 형성하였다. 상기 전자수송층 상부에 LiF 0.5nm(전자주입층)과 Al 60nm(캐소드)를 순차적으로 진공증착하여, 표 2에 표시된 바와 같은 유기전기발광소자를 제조하였다. 이 유기전기발광소자를 비교샘플 1로 하였다.The anode was prepared by cutting Corning's 15 Ω / cm 2 (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaning the substrate in acetone, isopropyl alcohol and pure water for 15 minutes each, Ozone cleaning was used. 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 (b) represented by Formula (b) (5% doped) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to produce an organic electroluminescent device as shown in Table 2. [ This organic electroluminescent device was referred to as Comparative Sample 1.

Figure pat00040
Figure pat00040

실시예 1~200.Examples 1-200.

상기 비교예 1 중, 발광층 형광 도판트 화합물로서 화합물 b 대신 상기 합성예에 개시된 화학식 1~297 중에서 선택된 하나의 화합물을 발광층 형광 청색 도판트 화합물로 각각 사용한 것을 제외하고는 상기 비교예 1과 동일한 방법으로 ITO/2-TNATA(80nm)/α-NPD(30nm)/[화합물 a+형광 청색 도판트 화합물 1~297 중 하나(5%)](30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)의 구조를 갖는 유기전기발광소자를 제조하였다. 이 유기전기발광소자를 각각 본 발명의 샘플 1 내지 200으로 하였다.The same procedure as in Comparative Example 1 was carried out except that the compound represented by the formula (1) was used instead of the compound (b) as the light emitting layer fluorescent dopant compound (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) / (30 nm) / (compound a + one of fluorescent blue dopant compounds 1 to 297 An organic electroluminescent device having a structure of Al (60 nm) was prepared. These organic electroluminescent devices were used as Samples 1 to 200 of the present invention.

시험예 1: 비교샘플 1 및 본 발명의 샘플 1~200의 발광 특성 평가Test Example 1: Evaluation of luminescence characteristics of Comparative Sample 1 and Samples 1 to 200 of the present invention

비교샘플 1 및 본 발명의 샘플 1~200에 대하여, Keithley sourcemeter "2400", KONIKA MINOLTA "CS-2000"을 이용하여 발광휘도, 발광효율, 발광피크를 각각 평가하여, 그 결과를 하기 [제2표군(群)]에 나타내었다. 상기 샘플들은 448~463nm 범위에서 청색 발광피크값을 보여주었다.The luminescence brightness, the luminescence efficiency and the luminescence peak were evaluated using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for the comparative sample 1 and the samples 1 to 200 of the present invention, (Group)]. The samples showed blue emission peak values in the range of 448 to 463 nm.

[제2표군(群)][Second group (group)]

Figure pat00041
Figure pat00042
Figure pat00043
Figure pat00044
Figure pat00045
Figure pat00046
Figure pat00041
Figure pat00042
Figure pat00043
Figure pat00044
Figure pat00045
Figure pat00046

Claims (9)

하기 화학식 1 또는 화학식 2로 표시되는 유기발광화합물:
[화학식1]
Figure pat00047


[화학식2]
Figure pat00048

상기 화학식 1 및 2에서,
R1, R2, R3 및 R4는 각각 독립적으로 수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, 할로겐, 니트릴, CF3,Si(CH3)3,또는 Si(C6H5)3기 이거나,
수소원자, C1~C10의 직쇄 또는 분지쇄 알킬, 할로겐, 니트릴, CF3,Si(CH3)3및 Si(C6H5)3기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 나프틸, 페난트레닐, 플루오레닐, 피레닐, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤즈옥사졸, 벤조티아졸, 카바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌 또는 디히드로인돌이며;
X, Y 및 Z은 각각 독립적으로 부존재 또는 C1~C10의 직쇄 또는 분지쇄 알킬기로 치환 또는 비치환된 메틸렌기이고, 부존재가 아닌 경우 Ar1, Ar2 또는 Ar3와 6~8원환을 형성하며;
W는 부존재, 단순결합, O, S, 하나 이상의 메틸 또는 페닐기로 치환된 메틸렌, 또는 카보닐기이고, 부존재가 아닌 경우 Ar1 및 Ar4와 5~8원환을 형성하며;
Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로 중소소원자, C1~C10의 직쇄 또는 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3,Si(CH3)3,Si(C6H5)3,C(C6H5)3,페닐, 중수소로 치환된 페닐, 나프틸기로 치환된 페닐, 하나 이상의 페닐기로 치환된 페닐, 나프틸, 피리디닐, 피리미디닐, 벤즈옥사졸, 벤조티아졸 및 9,9-디메틸플루오레닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이다.An organic luminescent compound represented by the following formula (1) or (2):
[Chemical Formula 1]
Figure pat00047


(2)
Figure pat00048

In the above Formulas 1 and 2,
R1, R2, R3 and R4 are each independently a hydrogen atom, a linear or branched alkyl, halogen, nitrile of C1 ~ C10, CF 3, Si (CH 3) 3, or Si (C 6 H 5) or 03,
A hydrogen atom, a linear or branched alkyl, halogen, nitrile of C1 ~ C10, CF 3, Si (CH 3) 3 and Si (C 6 H 5) with one or more substituents selected from the group consisting of 3-group-substituted or unsubstituted Wherein R is selected from the group consisting of phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, Dibenzofurane, dibenzothiophene, benzimidazole, quinoline, indole or dihydroindole;
X, Y and Z each independently represent a methylene group which is unsubstituted or substituted or unsubstituted with a linear or branched alkyl group having 1 to 10 carbon atoms, and forms a 6- to 8-membered ring with Ar1, Ar2 or Ar3 when it is not present;
W is absent, a simple bond, O, S, a methylene or carbonyl group substituted with at least one methyl or phenyl group, and when not present, forms a 5- to 8-membered ring with Ar1 and Ar4;
Ar1, Ar2, Ar3 and Ar4 each independently represent a small wish Here, linear or branched alkyl, alkoxy, halogen, nitrile of C1 ~ C10 of C1 ~ C10, CF 3, Si (CH 3) 3, Si (C 6 H 5 ) 3 , C (C 6 H 5 ) 3 , phenyl, phenyl substituted with deuterium, phenyl substituted with a naphthyl group, phenyl substituted with one or more phenyl groups, naphthyl, pyridinyl, pyrimidinyl, benzoxazole, A 6 to 30 aryl group or a 5 to 60 heteroaryl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of benzothiazole and 9,9-dimethylfluorenyl group. 제 1 항에 있어서,
상기 6~30의 아릴기 또는 5~60의 헤테로아릴기는 페닐, 나프틸, 페난트레닐, 플루오레닐, 9,9-디메틸플루오레닐, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 이미다졸, 트리아졸, 벤즈옥사졸, 벤조티아졸, 카바졸, 디벤조퓨란, 디벤조티오펜, 벤즈이미다졸, 퀴놀린, 인돌, 디히드로인돌, 피레닐,
Figure pat00049
,
Figure pat00050
,
Figure pat00051
및
Figure pat00052
로 이루어진 군으로부터 선택되는 것을 특징으로 하는 유기발광화합물.The method according to claim 1,
Wherein the 6 to 30 aryl group or the 5 to 60 heteroaryl group is selected from the group consisting of phenyl, naphthyl, phenanthrenyl, fluorenyl, 9,9-dimethylfluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, , Triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, dihydroindole, pyrenyl,
Figure pat00049
,
Figure pat00050
,
Figure pat00051
And
Figure pat00052
≪ / RTI > 제 1 항에 있어서,
R1, R2, R3 및 R4는 수소원자 또는 메틸기이며;
X, Y 및 Z은 각각 독립적으로 부존재 또는 2개의 메틸기로 치환된 메틸렌기이고, 부존재가 아닌 경우 Ar1, Ar2 또는 Ar3와 6원환을 형성하며;
W는 부존재, 단순결합, O, S, 하나 이상의 메틸 또는 페닐기로 치환된 메틸렌, 또는 카보닐기이고, 부존재가 아닌 경우 Ar1 및 Ar4와 5~6원환을 형성하며;
Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로 중소소원자, C1~C5의 직쇄 또는 분지쇄 알킬, C1~C5의 알콕시, 할로겐, 니트릴, CF3,Si(CH3)3,Si(C6H5)3,C(C6H5)3,페닐, 중수소로 치환된 페닐, 나프틸기로 치환된 페닐, 2개의 페닐기로 치환된 페닐, 나프틸, 벤즈옥사졸, 벤조티아졸기 및 9,9-디메틸플루오레닐기로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 나프틸, 플루오레닐, 9,9-디메틸플루오레닐, 피리디닐, 피리미디닐, 벤즈옥사졸, 벤조티아졸, 카바졸, 디벤조퓨란, 디벤조티오펜, 피레닐,
Figure pat00053
,
Figure pat00054
,
Figure pat00055
및
Figure pat00056
로 이루어진 군으로부터 선택되는 것을 특징으로 하는 유기발광화합물.The method according to claim 1,
R1, R2, R3 and R4 are a hydrogen atom or a methyl group;
X, Y and Z each independently represent a methylene group which is unsubstituted or substituted with two methyl groups, and when not present, forms a 6-membered ring with Ar1, Ar2 or Ar3;
W is absent, a simple bond, O, S, methylene substituted with one or more methyl or phenyl groups, or a carbonyl group, and when not present, forms a 5- to 6-membered ring with Ar1 and Ar4;
C 1 -C 5 alkoxy, halogen, nitrile, CF 3 , Si (CH 3 ) 3 , Si (C 6 H 5 ), and the like, wherein Ar 1, Ar 2, Ar 3 and Ar 4 are each independently selected from the group consisting of a hydrogen atom, 5 ) 3 , C (C 6 H 5 ) 3 , phenyl, phenyl substituted with deuterium, phenyl substituted with naphthyl, phenyl substituted with two phenyl, naphthyl, benzoxazole, benzothiazole, -Dimethylfluorenyl group, phenyl, naphthyl, fluorenyl, 9,9-dimethylfluorenyl, pyridinyl, pyrimidinyl, benzoxazole, benzo Thiazole, carbazole, dibenzofuran, dibenzothiophene, pyrenyl,
Figure pat00053
,
Figure pat00054
,
Figure pat00055
And
Figure pat00056
≪ / RTI > 제 3 항에 있어서,
상기 유기발광화합물은 하기 화합물 1 내지 화합물 296 중의 어느 하나 인 것을 특징으로 하는 유기발광화합물:
Figure pat00057
Figure pat00058
Figure pat00059
Figure pat00060
Figure pat00061
Figure pat00062
Figure pat00063
Figure pat00064
Figure pat00065
Figure pat00066
Figure pat00067
Figure pat00068
Figure pat00069
The method of claim 3,
Wherein the organic light emitting compound is any one of the following compounds 1 to 296:
Figure pat00057
Figure pat00058
Figure pat00059
Figure pat00060
Figure pat00061
Figure pat00062
Figure pat00063
Figure pat00064
Figure pat00065
Figure pat00066
Figure pat00067
Figure pat00068
Figure pat00069
 제 1 항에 있어서,
상기 유기발광화합물이 유기전기발광소자용 재료인 것을 특징으로 하는 유기발광화합물.The method according to claim 1,
Wherein the organic light emitting compound is a material for an organic electroluminescence device. 제 5 항에 있어서,
상기 유기발광화합물이 유기전기발광소자용 재료 중 발광층 형광 청색 도판트 물질인 것을 특징으로 하는 유기발광화합물.6. The method of claim 5,
Wherein the organic luminescent compound is a luminescent blue phosphorescent dopant in an organic EL device. 음극과 양극 사이에 적어도 발광층을 포함하는 일층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기전기발광소자에 있어서,
상기 유기 박막층 중 적어도 1층 이상이 청구항 1의 유기발광화합물을 1종 단독으로 또는 2종 이상의 조합으로 함유하는 것을 특징으로 하는 유기전기발광소자.An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,
Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of claim 1 singly or in combination of two or more. 제 7 항에 있어서,
상기 유기발광화합물이 상기 유기 박막층 중 발광층에 발광층 형광 청색 도판트 물질로 함유되는 것을 특징으로 하는 유기전기발광소자.8. The method of claim 7,
Wherein the organic light emitting compound is contained in the light emitting layer of the organic thin film layer as a light emitting layer fluorescent blue dopant material. 제 7 항 또는 제 8 항에 있어서,
상기 유기전기발광소자가 양극, 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 및 음극이 이 순서대로 적층된 구조를 갖는 것을 특징으로 하는 유기전기발광소자.9. The method according to claim 7 or 8,
Wherein the organic electroluminescent device has a structure in which an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode are stacked in this order.
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