KR20090008811A - Novel oxime carbamate compounds, photopolymerization initiator and photopolymerizable composition containing the same - Google Patents

Novel oxime carbamate compounds, photopolymerization initiator and photopolymerizable composition containing the same Download PDF

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KR20090008811A
KR20090008811A KR1020070072069A KR20070072069A KR20090008811A KR 20090008811 A KR20090008811 A KR 20090008811A KR 1020070072069 A KR1020070072069 A KR 1020070072069A KR 20070072069 A KR20070072069 A KR 20070072069A KR 20090008811 A KR20090008811 A KR 20090008811A
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KR100895793B1 (en
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이창진
이재민
김동욱
윤성철
강영구
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한국화학연구원
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
    • C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
    • C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings

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Abstract

An oxime carbamate compound is provided to be usable for a photopolymerization initiator in the ultraviolet irradiation and to control the absorption spectrum of the photopolymerization initiator by introducing an aryl or heteroaryl substituent. An oxime carbamate compound is indicated as the chemical formula 1. In the chemical formula 1, R1 is (C6-C30) aryl or (C6-C30) heteroaryl; R11, R12, R13, R14 and R15 are independently hydrogen, linear or branched, saturated or unsaturated (C1-C12) alkyl, (C3-C8) cycloalkyl, (C1-C12) alkylcarbonyl, and (C6-C30) aryl or tri (C1-C12) alkylsiloxy; m is an integer of 0 or 1; and n is an integer of 1-20.

Description

신규한 옥심 카바메이트 화합물, 이를 함유하는 광중합 개시제 및 광중합성 조성물{Novel Oxime Carbamate Compounds, Photopolymerization Initiator And Photopolymerizable Composition Containing The Same}Novel Oxime Carbamate Compounds, Photopolymerization Initiator And Photopolymerizable Composition Containing The Same

본 발명은 신규한 옥심 카바메이트 화합물, 이를 함유하는 광중합 개시제 및 광중합성 조성물에 관한 것이다.The present invention relates to novel oxime carbamate compounds, photopolymerization initiators and photopolymerizable compositions containing them.

광중합 개시제를 포함하는 광중합성 조성물은 조사된 빛에 의해 선택적으로 경화되어 패턴을 형성할 수 있기 때문에, 광경화성 잉크, 감광성 인쇄판, 각종 포토레지스트 등에 사용되고 있다. 이러한 특성을 갖는 광중합 개시제로는 아세토페논 유도체, 벤조페논 유도체, 바이이미다졸 유도체, 아실 포스핀 옥사이드 유도체, 트리아진 유도체, 옥심 유도체 등 여러 종류가 알려져 있다. 이 중에서도 옥심 유도체는 색깔을 거의 띠지 않고 투과도가 좋으며 자외선 조사에 의한 라디칼 발생 효율이 높을 뿐만 아니라 조성물 내에서 안정성과 상용성이 뛰어나다는 장점을 지니고 있다.Since the photopolymerizable composition containing a photoinitiator can be hardened selectively by the irradiated light and can form a pattern, it is used for photocurable inks, photosensitive printing plates, various photoresists, etc. Photopolymerization initiators having such characteristics are known as acetophenone derivatives, benzophenone derivatives, biimidazole derivatives, acyl phosphine oxide derivatives, triazine derivatives, oxime derivatives. Among them, the oxime derivative has almost no color, good permeability, high radical generation efficiency by ultraviolet irradiation, and excellent stability and compatibility in the composition.

대한민국 공개특허 10-2006-0064700호에는 잠재성 설폰산으로서 옥심 설포네 이트에 대해 기술하고 있다. 특히 옥심 유도체 가운데에서도 옥심 에스테르 유도체는 광중합 개시제로서 널리 알려져 있다. 대한민국 공개특허공보 10-2004-0007700호와 10-2007-0044753호에는 옥심 에스테르 유도체는 광중합 개시제라는 것이 공지되어 있다. 또한 대한민국 공개특허공보 10-2007-0018850호에는 옥심 에스테르 화합물 및 이를 포함하는 광중합 조성물에 대해 기재하고 있다. Korean Patent Publication No. 10-2006-0064700 describes oxime sulfonate as a latent sulfonic acid. In particular, among oxime derivatives, oxime ester derivatives are widely known as photopolymerization initiators. Korean Patent Laid-Open Publication Nos. 10-2004-0007700 and 10-2007-0044753 disclose that oxime ester derivatives are photopolymerization initiators. In addition, the Republic of Korea Patent Publication No. 10-2007-0018850 discloses an oxime ester compound and a photopolymerization composition comprising the same.

이와 같이, 다양한 종류의 광중합 개시제가 알려져 있으나, 광중합 반응 기술에 있어서 반응성이 높고, 제조가 용이하며 취급이 용이한 광중합 개시제에 대한 필요성이 여전히 존재한다. 추가로, 이러한 새로운 광중합 개시제는, 예를 들면, 열 안정성 및 저장 안정성과 같은 특징에 대한 산업 현장의 높은 요구를 충족시켜야 한다.As such, various kinds of photopolymerization initiators are known, but there is still a need for a photopolymerization initiator that is highly reactive, easy to manufacture, and easy to handle in photopolymerization technology. In addition, these new photopolymerization initiators must meet the high demands of the industrial site for features such as, for example, thermal stability and storage stability.

본 발명자들은 상기한 문제점들을 해결하기 위하여 질소-산소간 결합의 끊김에 의한 라디칼 생성이 유리한 옥심계 구조를 유지하되, 우레탄기를 도입한 옥심 카바메이트 화합물을 개발하였다.The present inventors have developed an oxime carbamate compound incorporating a urethane group while maintaining an oxime-based structure, which is advantageous in generating radicals by breaking nitrogen-oxygen bonds, in order to solve the above problems.

따라서 본 발명의 목적은 신규한 옥심 카바메이트 화합물을 제공하는 것이고, 이를 함유하는 광중합 개시제 및 광중합성 조성물을 제공하는 데 또 다른 목적이 있다.Accordingly, an object of the present invention is to provide a novel oxime carbamate compound, and another object is to provide a photopolymerization initiator and a photopolymerizable composition containing the same.

본 발명은 하기 화학식 1로 표시되는 신규한 옥심 카바메이트 화합물, 이를 함유하는 광중합 개시제 및 광중합성 조성물에 관한 것으로서, 본 발명에 따른 옥심 카바메이트 화합물은 자외선 조사시 광중합 개시제로 사용될 수 있으며, 다양한 아릴 또는 헤테로아릴 치환기가 도입되어 광중합 개시제의 흡수 스텍트럼을 조절할 수 있는 장점이 있다.The present invention relates to a novel oxime carbamate compound represented by the following formula (1), a photopolymerization initiator and a photopolymerizable composition containing the same, wherein the oxime carbamate compound according to the present invention can be used as a photopolymerization initiator upon ultraviolet irradiation, and various aryls. Alternatively, a heteroaryl substituent may be introduced to control the absorption spectrum of the photopolymerization initiator.

[화학식 1][Formula 1]

Figure 112007052243254-PAT00002
Figure 112007052243254-PAT00002

[상기 화학식 1에서, [In Formula 1,

R1은 (C6-C30)아릴 또는 (C6-C30)헤테로아릴이고;R 1 is (C 6 -C 30 ) aryl or (C 6 -C 30 ) heteroaryl;

상기 R1의 아릴 또는 헤테로아릴은 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, 산소, 질소 또는 황을 포함하는 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C1-C12)알콕시, (C1-C12)알콕시(C1-C12)알킬, (C3-C8)시클로알킬, (C3-C8)시클로알킬(C1-C12)알킬, 산소, 질소 또는 황을 헤테로고리 안에 포함하는 3원 내지 7원의 포화 또는 불포화 헤테로시클로알킬, 산소, 질소 또는 황을 헤테로고리 안에 포함하는 3원 내지 7원의 포화 또는 불포화 헤테로시클로알킬(C1-C12)알킬, 히드록시(C1-C12)알킬, (C3-C8)시클로알킬(C1-C12)알콕시, (C1-C12)알킬카르보닐, (C1-C12)알콕시카르보닐, (C1-C12)알콕시카르보닐(C1-C12)알킬카르보닐, (C1-C12)알킬카르보닐옥시, (C6-C30)아릴, (C6-C30)헤테로아릴, (C6-C30)아릴카르보닐, (C6-C30)헤테로아릴카르보닐, (C6-C30)아릴티오, (C6-C30)헤테로아릴티오, 카르복실산, (C6-C30)헤테로아릴카르보닐(C6-C30)아릴티오, 할로겐, (C6-C30)아릴옥시, (C6-C30)아릴옥시카르보닐, (C6-C30)아릴옥시카르보닐(C1-C12)알킬카르보닐, (C6-C30)헤테로아릴옥시, (C6-C30)헤테로아릴옥시카르보닐, (C6-C30)헤테로아릴옥시카르보닐(C1-C12)알킬카르보닐, 히드록시, 시아노, 니트로, 트리(C1-C12)알킬실록시, 모노 또는 디 (C1-C12)알킬아미노카르보닐, 아 미노카르보닐, -O(CH2CH2O)nH, -SR11, -SOR12, -SO2R13 및 -NR14R15로부터 선택된 하나이상의 치환기로 더 치환될 수 있고, R1과 R2는 (C1-C3)알킬렌 또는 (C2-C4)알케닐렌으로 연결되어 고리를 형성할 수 있으며;Aryl or heteroaryl of said R 1 is a saturated or unsaturated straight-chain or grinding (C 1 -C 12) alkyl, oxygen, nitrogen or sulfur, or a saturated or unsaturated straight chain of grinding comprising the (C 1 -C 12) alkyl, ( C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkoxy (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkyl (C 1 -C 12 3-7 membered saturated or unsaturated heterocycloalkyl containing alkyl, oxygen, nitrogen or sulfur in the heterocycle 3-7 membered saturated or unsaturated heterocycloalkyl comprising oxygen, nitrogen or sulfur in the heterocycle (C 1 -C 12 ) alkyl, hydroxy (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl (C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkylcarbonyl, ( C 1 -C 12 ) alkoxycarbonyl, (C 1 -C 12 ) alkoxycarbonyl (C 1 -C 12 ) alkylcarbonyl, (C 1 -C 12 ) alkylcarbonyloxy, (C 6 -C 30 ) aryl, (C 6 -C 30) heteroaryl, (C 6 -C 30) arylcarbonyl, (C 6 -C 30) H. Loa reel-carbonyl, (C 6 -C 30) arylthio, (C 6 -C 30) heteroaryl, alkylthio, carboxyl, (C 6 -C 30) heteroaryl, carbonyl (C 6 -C 30) arylthio , Halogen, (C 6 -C 30 ) aryloxy, (C 6 -C 30 ) aryloxycarbonyl, (C 6 -C 30 ) aryloxycarbonyl (C 1 -C 12 ) alkylcarbonyl, (C 6 -C 30 ) heteroaryloxy, (C 6 -C 30 ) heteroaryloxycarbonyl, (C 6 -C 30 ) heteroaryloxycarbonyl (C 1 -C 12 ) alkylcarbonyl, hydroxy, cyano, Nitro, tri (C 1 -C 12 ) alkylsiloxy, mono or di (C 1 -C 12 ) alkylaminocarbonyl, aminocarbonyl, -O (CH 2 CH 2 O) n H, -SR 11 , May be further substituted with one or more substituents selected from -SOR 12 , -SO 2 R 13 and -NR 14 R 15 , wherein R 1 and R 2 are (C 1 -C 3 ) alkylene or (C 2 -C 4 ) May be linked to alkenylene to form a ring;

R2 및 R3는 서로 독립적으로 수소, 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C3-C8)시클로알킬, (C1-C12)알콕시, (C1-C12)알킬티오, (C6-C30)아릴, (C6-C30)아르(C1-C12)알킬, (C1-C30)알킬(C6-C30)아릴, (C1-C30)알킬카르보닐, (C1-C12)알콕시카르보닐, (C1-C12)알킬카르보닐옥시, (C6-C30)아르(C1-C12)알킬카르보닐, (C6-C30)아르(C1-C12)알콕시카르보닐, (C6-C30)아르(C1-C12)알킬카르보닐옥시, (C6-C30)아르(C1-C12)알콕시, (C6-C30)아르(C1-C12)알킬티오 또는 메타아크릴레이트(methacrylate)이고, 상기 R2 및 R3의 알킬 또는 아릴기는 (C1-C12)알킬카르보닐, (C1-C12)알킬카르보닐옥시, (C1-C12)알콕시카르보닐, (C1-C12)알콕시, (C1-C12)알킬티오, 트리(C1-C12)알킬실릴, 트리(C1-C12)알콕시실릴 또는 트리(C6-C30)아릴실릴로 더 치환될 수 있으며; R 2 and R 3 independently of one another are hydrogen, straight or branched saturated or unsaturated (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 1 -C 12 ) alkoxy, (C 1- C 12 ) alkylthio, (C 6 -C 30 ) aryl, (C 6 -C 30 ) ar (C 1 -C 12 ) alkyl, (C 1 -C 30 ) alkyl (C 6 -C 30 ) aryl, ( C 1 -C 30 ) alkylcarbonyl, (C 1 -C 12 ) alkoxycarbonyl, (C 1 -C 12 ) alkylcarbonyloxy, (C 6 -C 30 ) ar (C 1 -C 12 ) alkylcarbon carbonyl, (C 6 -C 30) ar (C 1 -C 12) alkoxycarbonyl, (C 6 -C 30) ar (C 1 -C 12) alkylcarbonyloxy, (C 6 -C 30) ar ( C 1 -C 12 ) alkoxy, (C 6 -C 30 ) ar (C 1 -C 12 ) alkylthio or methacrylate, wherein the alkyl or aryl group of R 2 and R 3 is (C 1 -C 12 ) alkylcarbonyl, (C 1 -C 12 ) alkylcarbonyloxy, (C 1 -C 12 ) alkoxycarbonyl, (C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkylthio, tri ( C 1 -C 12 ) alkylsilyl, tri (C 1 -C 12 ) alkoxysilyl or tri (C 6 -C 30 ) arylsilyl May be further substituted;

R11, R12, R13, R14 및 R15는 서로 독립적으로 수소, 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C3-C8)시클로알킬, (C1-C12)알킬카르보닐, (C6-C30)아릴 또는 트리(C1-C12)알킬실록시이며;R 11 , R 12 , R 13 , R 14 and R 15 independently of one another are hydrogen, straight or branched saturated or unsaturated (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 1- C 12 ) alkylcarbonyl, (C 6 -C 30 ) aryl or tri (C 1 -C 12 ) alkylsiloxy;

m은 0 또는 1의 정수이고;m is an integer of 0 or 1;

n은 1 내지 20의 정수이다.]n is an integer from 1 to 20.]

본 발명에 따른 상기 화학식 1의 옥심 카바메이트 화합물은 기존에 공개된 옥심 에스테르 유도체의 광개시 반응과는 달리, 자외선을 흡수하여 하기 반응식 1 에 나타낸 단계를 거쳐 아민 라디칼을 형성하고 상기 형성된 아민 라디칼이 광중합에 관여하는 것을 특징으로 한다.The oxime carbamate compound of Chemical Formula 1 according to the present invention, unlike the photoinitiation reaction of the oxime ester derivative disclosed in the prior art, absorbs ultraviolet rays to form amine radicals through the steps shown in Scheme 1 below and the amine radicals formed It is characterized by participating in photopolymerization.

[반응식 1]Scheme 1

Figure 112007052243254-PAT00003
Figure 112007052243254-PAT00003

[상기 반응식 1에서 R1, R2, R3 및 m은 화학식 1에서의 정의와 동일하다.][In Formula 1, R 1 , R 2 , R 3 and m are the same as defined in Formula 1.]

상기 반응식 1에 나타낸 바와 같이, 생성된 아민 라디칼은 직접 라디칼 중합에 참여할 수 있다.As shown in Scheme 1 above, the resulting amine radicals may participate in direct radical polymerization.

본 발명에 따른 옥심 카바메이트 화합물은 하기 화학식 2 내지 화학식 4로 예시될 수 있다.The oxime carbamate compound according to the present invention may be exemplified by the following Chemical Formulas 2 to 4.

[화학식 2][Formula 2]

Figure 112007052243254-PAT00004
Figure 112007052243254-PAT00004

[화학식 3][Formula 3]

Figure 112007052243254-PAT00005
Figure 112007052243254-PAT00005

[화학식 4][Formula 4]

Figure 112007052243254-PAT00006
Figure 112007052243254-PAT00006

[상기 화학식 2 내지 화학식 4에서,[In Formula 2 to Formula 4,

A는 화학결합이거나

Figure 112007052243254-PAT00007
이며;A is a chemical bond
Figure 112007052243254-PAT00007
Is;

B 및 D는 서로 독립적으로 O, S, CR41R42 또는 NR43이며;B and D are independently of each other O, S, CR 41 R 42 or NR 43 ;

R2 및 R3는 화학식 1에서의 정의와 동일하며;R 2 and R 3 are the same as defined in formula (1);

R21, R22, R23, R24, R25, R31, R32, R33, R34, R35, R36, R37, R38, R51, R52, R53, R54, R55, R56 및 R57은 서로 독립적으로 수소, 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, 산소, 질소 또는 황을 포함하는 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C1-C12)알콕시, (C1-C12)알콕시(C1-C12)알킬, (C3-C8)시클로알킬, (C3-C8)시클로알킬(C1-C12)알킬, 산소, 질소 또는 황을 헤테로고리 안에 포함하는 3원 내지 7원의 포화 또는 불포화 헤테로시클로알킬, 산소, 질소 또는 황을 헤테로고리 안에 포함하는 3원 내지 7원의 포화 또는 불포화 헤테로시클로알킬(C1-C12)알킬, 히드록시(C1-C12)알킬, (C3-C8)시클로알킬(C1-C12)알콕시, (C1-C12)알킬카르보닐, (C1-C12)알콕시카르보닐, (C1-C12)알콕시카르보닐(C1-C12)알킬카르보닐, (C1-C12)알킬카르보닐옥시, (C6-C30)아릴, (C6-C30)헤테로아릴, (C6-C30)아릴카르보닐, (C6-C30)헤테로아릴카르보닐, (C6-C30)아릴티오, (C6-C30)헤테로아릴티오, 카르복실산, (C6-C30)헤테로아릴카르보닐(C6-C30)아릴티오, 할로겐, (C6-C30)아릴옥시, (C6-C30)아릴옥시카르보닐, (C6-C30)아릴옥시카르보닐(C1-C12)알킬카르보닐, (C6-C30)헤테로아릴옥시, (C6-C30)헤테로아릴옥시카르보닐, (C6-C30)헤테로아릴옥시카르보닐(C1-C12)알킬카르보닐, 히드록시, 시아노, 니트로, 트리(C1-C12)알킬실록시, 모노 또는 디 (C1-C12)알킬아미노카르 보닐, 아미노카르보닐, -O(CH2CH2O)nH, -SR11, -SOR12, -SO2R13 또는 -NR14R15이거나, R21 내지 R25가 서로 인접한 R21 내지 R25와 (C1-C3)알킬렌 또는 (C2-C4)알케닐렌으로 결합하여 융합고리를 형성할 수 있거나 R2와 (C1-C3)알킬렌 또는 (C2-C4)알케닐렌으로 연결되어 고리를 형성할 수 있으며;R 21 , R 22 , R 23 , R 24 , R 25 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 51 , R 52 , R 53 , R 54 , R 55 , R 56 and R 57 are independently of each other hydrogen, straight or branched, saturated or unsaturated (C 1 -C 12 ) alkyl, straight or branched, saturated or unsaturated (C 1- C 12 ) alkyl, (C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkoxy (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkyl (C 1 -C 12 ) 3- to 7-membered saturated or unsaturated heterocycloalkyls containing alkyl, oxygen, nitrogen or sulfur in the heterocycle 3- to 7-membered containing oxygen, nitrogen or sulfur in the heterocycle Saturated or unsaturated heterocycloalkyl (C 1 -C 12 ) alkyl, hydroxy (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl (C 1 -C 12 ) alkoxy, (C 1 -C 12 ) Alkylcarbonyl, (C 1 -C 12 ) alkoxycarbonyl, (C 1 -C 12 ) alkoxycarbonyl (C 1 -C 12 ) alkylcarbonyl, (C 1 -C 12 ) alkylcarbonyloxy, (C 6 -C 30 ) aryl, (C 6 -C 30 ) heteroaryl, (C 6 -C 30 ) arylcarbonyl, (C 6 -C 30 ) heteroarylcarbonyl, ( C 6 -C 30 ) arylthio, (C 6 -C 30 ) heteroarylthio, carboxylic acid, (C 6 -C 30 ) heteroarylcarbonyl (C 6 -C 30 ) arylthio, halogen, (C 6 -C 30 ) aryloxy, (C 6 -C 30 ) aryloxycarbonyl, (C 6 -C 30 ) aryloxycarbonyl (C 1 -C 12 ) alkylcarbonyl, (C 6 -C 30 ) heteroaryl Oxy, (C 6 -C 30 ) heteroaryloxycarbonyl, (C 6 -C 30 ) heteroaryloxycarbonyl (C 1 -C 12 ) alkylcarbonyl, hydroxy, cyano, nitro, tri (C 1 -C 12 ) alkylsiloxy, mono or di (C 1 -C 12 ) alkylaminocarbonyl, aminocarbonyl, -O (CH 2 CH 2 O) n H, -SR 11 , -SOR 12 , -SO 2 R 13 or —NR 14 R 15, or R 21 to R 25 are bonded to each other with R 21 to R 25 and (C 1 -C 3 ) alkylene or (C 2 -C 4 ) alkenylene to form a fused ring You can do it R2 and (C 1 -C 3) alkylene or (C 2 -C 4) alkenylene may form a ring;

R11, R12, R13, R14, R15, R41, R42 및 R43는 서로 독립적으로 수소, 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C3-C8)시클로알킬, (C1-C12)알킬카르보닐, (C6-C30)아릴 또는 트리(C1-C12)알킬실록시이며;R 11 , R 12 , R 13 , R 14 , R 15 , R 41 , R 42 and R 43 are independently of each other hydrogen, straight or branched, saturated or unsaturated (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 1 -C 12 ) alkylcarbonyl, (C 6 -C 30 ) aryl or tri (C 1 -C 12 ) alkylsiloxy;

m은 0 또는 1의 정수이고;m is an integer of 0 or 1;

n은 1 내지 20의 정수이다.]n is an integer from 1 to 20.]

상기 화학식 2에서 A에 원소가 존재하지 않고 단순히 탄소와 탄소가 연결되어 있는 상태를 ‘화학결합’이라고 한다.In the above Formula 2, an element does not exist in A and is simply referred to as 'chemical bond'.

본 발명에 따른 옥심 카바메이트 화합물은 더욱 바람직하게 하기 화학식 5 내지 화학식 8로 예시될 수 있다.The oxime carbamate compound according to the present invention may be more preferably exemplified by the following Chemical Formulas 5 to 8.

[화학식 5][Formula 5]

Figure 112007052243254-PAT00008
Figure 112007052243254-PAT00008

[화학식 6][Formula 6]

Figure 112007052243254-PAT00009
Figure 112007052243254-PAT00009

[화학식 7][Formula 7]

Figure 112007052243254-PAT00010
Figure 112007052243254-PAT00010

[화학식 8][Formula 8]

Figure 112007052243254-PAT00011
Figure 112007052243254-PAT00011

[상기 화학식 5 내지 화학식 8에서,[In Formula 5 to Formula 8,

R2 및 R3는 서로 독립적으로 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 펜틸, 헥실, 에틸헥실, 헵틸, 옥틸, 이소옥틸, 노닐, 메톡시, 에톡시, 프로폭시, 부톡시, 메틸티오, 에틸티오, 부틸티오, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 페닐, 비페닐, 나프틸, 안트릴, 플루오레닐, 벤질, 톨릴, 메타아크릴레이트(methacrylate), 트리메톡시실릴프로필, 트리에톡시실릴프로필 또는 트리페녹시실릴부틸이고;R 2 and R 3 independently of one another are hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, methoxy, ethoxy, propoxy, Butoxy, methylthio, ethylthio, butylthio, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, anthryl, fluorenyl, benzyl, tolyl, methacrylate, Trimethoxysilylpropyl, triethoxysilylpropyl or triphenoxysilylbutyl;

R41, R42 및 R43은 서로 독립적으로 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 펜틸, 헥실, 에틸헥실, 헵틸, 옥틸, 이소옥틸, 노닐, 시클로프로 필, 시클로부틸, 시클로펜틸, 시클로헥실, 페닐, 비페닐, 나프틸, 안트릴 또는 플루오레닐이고;R 41 , R 42 and R 43 independently of one another are hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, cyclopropyl, cyclobutyl , Cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, anthryl or fluorenyl;

Z는 하기 구조의 아릴 또는 헤테로아릴이며;Z is aryl or heteroaryl of the structure:

Figure 112007052243254-PAT00012
Figure 112007052243254-PAT00012

E는 N 또는 NO이고; F는 CH 또는 N이고; G는 CH 또는 N이고; H는 S, O 또는 NH이고; I는 CH 또는 N이고; J는 CH 또는 N이고; Q는 S, O 또는 NH이고; R는 CH 또는 N이고; W는 CH, N 또는 NO이고;E is N or NO; F is CH or N; G is CH or N; H is S, O or NH; I is CH or N; J is CH or N; Q is S, O or NH; R is CH or N; W is CH, N or NO;

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

본 발명에 따른 옥심 카바메이트 화합물은 하기의 화합물로 예시될 수 있으나, 하기의 화합물이 본 발명을 한정하는 것은 아니다.The oxime carbamate compound according to the present invention may be exemplified by the following compounds, but the following compounds do not limit the present invention.

Figure 112007052243254-PAT00013
Figure 112007052243254-PAT00013

Figure 112007052243254-PAT00014
Figure 112007052243254-PAT00014

Figure 112007052243254-PAT00015
Figure 112007052243254-PAT00015

Figure 112007052243254-PAT00016
Figure 112007052243254-PAT00016

Figure 112007052243254-PAT00017
Figure 112007052243254-PAT00017

Figure 112007052243254-PAT00018
Figure 112007052243254-PAT00018

Figure 112007052243254-PAT00019
Figure 112007052243254-PAT00019

Figure 112007052243254-PAT00020
Figure 112007052243254-PAT00020

Figure 112007052243254-PAT00021
Figure 112007052243254-PAT00021

또한 본 발명은 광중합 개시제 및 광중합성 조성물을 제공하며, 본 발명에 따른 광중합 개시제 및 광중합성 조성물은 상기 화학식 1로 표시되는 신규한 옥심 카바메이트 화합물을 유효성분으로 포함하는 것을 특징으로 한다.The present invention also provides a photopolymerization initiator and a photopolymerizable composition, the photopolymerization initiator and the photopolymerizable composition according to the present invention is characterized in that it comprises a novel oxime carbamate compound represented by the formula (1) as an active ingredient.

본 발명에 따른 신규한 옥심 카바메이트 화합물은 옥심 화합물과 이소시아네이트 화합물 간의 반응을 통해 제조되며, 상기 옥심 카바메이트 화합물은 빛에 노광되어 각종 불포화기의 중합을 개시하는 광중합 개시제로서 효과적으로 작용할 수 있다.The novel oxime carbamate compound according to the present invention is prepared through a reaction between an oxime compound and an isocyanate compound, and the oxime carbamate compound can act effectively as a photopolymerization initiator which is exposed to light to initiate polymerization of various unsaturated groups.

이하에서, 본 발명을 실시예에 의거하여 본 발명에 따른 신규한 옥심 카바메이트 화합물의 제조방법을 예시한다. 그러나, 하기의 실시예들은 본 발명에 대한 이해를 돕기 위한 것으로서, 본 발명의 범위가 여기에 국한되는 것은 아니다. 본 발명의 임의의 변형 또는 변화는, 명세서 및 첨가된 청구범위에 포함된 사항의 범위 내에서 당업자에 의해 용이하게 이루어질 수 있다.Hereinafter, the production method of the novel oxime carbamate compound according to the present invention based on the present invention. However, the following examples are provided to aid the understanding of the present invention, and the scope of the present invention is not limited thereto. Any modification or change of the present invention can be easily made by those skilled in the art within the scope of the matter contained in the specification and the appended claims.

[실시예 1] Example 1

[(9-[(9- ethylethyl -6-(1-(-6- (1- ( phenylcarbamoyloxyiminophenylcarbamoyloxyimino )) ethylethyl )-)- carbazolcarbazol )-3-) -3- ylyl ] (thiophen-2-yl)methanone 의 제조Preparation of (thiophen-2-yl) methanone

Figure 112007052243254-PAT00022
Figure 112007052243254-PAT00022

1-[9-ethyl-6-(thiophene-2-carbonyl)-carbazol-3-yl]-ethanone 의 제조Preparation of 1- [9-ethyl-6- (thiophene-2-carbonyl) -carbazol-3-yl] -ethanone

CH2Cl2 40ml에 9-에틸카바졸(5.0g; 25.6mmol)을 첨가하고, 티오펜-2-카보닐클로라이드 3.75g(25.6mmol) 및 AlCl3 3.40g(25.6mmol)을 가하였다. 실온에서 4시간 동안 교반한 후, 아세틸 클로라이드 2.0g(25.6mmol)와 AlCl3 3.4g(25.6mmol)를 가하였다. 상기 반응 혼합물은 실온에서 밤새 교반한 후 반응 혼합물에 얼음물을 넣어 반응을 종료시켰다. 반응생성물은 CH2Cl2로 추출한다. CH2Cl2 층을 H20, 포화 NaHCO3 수용액 및 염수로 세척하고, 무수 MgSO4로 건조시키고, 감압하에 농축시켜 표제화합물인 1-[9-ethyl-6-(thiophene-2-carbonyl)-carbazol-3-yl]-ethanone를 회색 고체(9.26g, 조생성물)로 수득하였다.To 40 ml of CH 2 Cl 2 was added 9-ethylcarbazole (5.0 g; 25.6 mmol), followed by 3.75 g (25.6 mmol) of thiophene-2-carbonylchloride and 3.40 g (25.6 mmol) of AlCl 3 . After stirring for 4 hours at room temperature, 2.0 g (25.6 mmol) of acetyl chloride and 3.4 g (25.6 mmol) of AlCl 3 were added thereto. The reaction mixture was stirred at room temperature overnight and then quenched by adding ice water to the reaction mixture. The reaction product is extracted with CH 2 Cl 2 . The CH 2 Cl 2 layer was washed with H 2 O, saturated aqueous NaHCO 3 and brine, dried over anhydrous MgSO 4 , and concentrated under reduced pressure to give the title compound 1- [9-ethyl-6- (thiophene-2-carbonyl) -carbazol-3-yl] -ethanone was obtained as a gray solid (9.26 g, crude).

1H-NMR (δ, ppm, CDCl3) : 1.50 (t, 3H), 2.73 (s, 3H), 4.45 (q, 2H), 7.22 (td, 1H), 7.50 (dd, 2H), 7.75 (m, 2H), 8.15 (dd, 2H), 8.80 (dd, 2H). 1 H-NMR (δ, ppm, CDCl 3 ): 1.50 (t, 3H), 2.73 (s, 3H), 4.45 (q, 2H), 7.22 (td, 1H), 7.50 (dd, 2H), 7.75 ( m, 2H), 8.15 (dd, 2H), 8.80 (dd, 2H).

(9-(9- ethylethyl -6-(1-(-6- (1- ( hydroxyiminohydroxyimino )) ethylethyl )-)- carbazolcarbazol -3--3- ylyl )() ( thiophenthiophen -2-yl) -2-yl) methanone 의methanone 제조 Produce

하이드록실암모늄 클로라이드 0.72g(10.4mmol), 나트륨 아세테이트 0.85g(10.4mmol) 및 H20 7.5ml의 혼합물에 1-[9-ethyl-6-(thiophene-2-carbonyl)-carbazol-3-yl]-ethanone 3.0g(8.6mmol) 및 N,N-디메틸아세트아미드(DMA) 15ml를 가하고, 4시간 동안 가열한 후, H20를 상기 반응 혼합물에 가하고, 생성된 황색 고체를 여과하여 제거한 다음, H20로 세척하고, CH2Cl2에 용해시켰다. 상기 CH2Cl2 용액을 무수 MgSO4로 건조시킨 후, 감압하에 농축시켜 갈색 계열의 황색 고체를 3.02g 수득하였다. 그 다음, 재침전시키고, 컬럼 크로마토그라피하여 목적 화합물인 (9-ethyl-6-(1-(hydroxyimino)ethyl)-carbazol-3-yl)(thiophen-2-yl)methanone를 황색 고체(1.5g; 48%)로 수득하였다.1- [9-ethyl-6- (thiophene-2-carbonyl) -carbazol-3-yl in a mixture of 0.72 g (10.4 mmol) hydroxyl ammonium chloride, 0.85 g (10.4 mmol) sodium acetate and 7.5 ml H 2 0 ] -ethanone 3.0 g (8.6 mmol) and 15 ml of N, N-dimethylacetamide (DMA) were added and heated for 4 hours, H 2 0 was added to the reaction mixture, and the resulting yellow solid was filtered off. Washed with H 2 O and dissolved in CH 2 Cl 2 . The CH 2 Cl 2 solution was dried over anhydrous MgSO 4, and concentrated under reduced pressure to yield 3.02 g of a brownish yellow solid. Then, the precipitate was reprecipitated and column chromatographed to give (9-ethyl-6- (1- (hydroxyimino) ethyl) -carbazol-3-yl) (thiophen-2-yl) methanone as a yellow solid (1.5 g). ; 48%).

1H-NMR (δ, ppm, CDCl3) : 1.49 (t, 3H), 2.41 (s, 3H), 4.43 (q, 2H), 7.21 (td, 1H), 7.48 (q, 2H), 7.75 (m, 2H), 7.87 (dd, 2H), 8.13 (dd, 1 H), 8.39 (d, 1 H), 8.71 (d, 1 H). 1 H-NMR (δ, ppm, CDCl 3 ): 1.49 (t, 3H), 2.41 (s, 3H), 4.43 (q, 2H), 7.21 (td, 1H), 7.48 (q, 2H), 7.75 ( m, 2H), 7.87 (dd, 2H), 8.13 (dd, 1H), 8.39 (d, 1H), 8.71 (d, 1H).

[(9-[(9- ethylethyl -6-(1-(-6- (1- ( phenylcarbamoyloxyiminophenylcarbamoyloxyimino )) ethylethyl )-)- carbazolcarbazol )-3-yl] () -3-yl] ( thiophenthiophen -2--2- ylyl )) methanone 의methanone 제조 Produce

100 mL 2-neck 둥근바닥플라스크에 (9-ethyl-6-(1-(hydroxyimino)ethyl)-carbazol-3-yl)(thiophen-2-yl)methanone 1.5 g (4.1 mmol) 과 phenyl isocyanate 0.67 mL (6.2 mmol) 를 디클로로메탄 10 mL 에 녹여서 저어주었다. 여기에 0.1 g의 dibutyltin dilaurate 를 첨가하고 12시간동안 추가로 저어주었다. 박층크로마토그래피로 반응이 다 진행되었음을 확인한 후, 디클로로메탄/물로 반응물을 추출하고 n-헥산에 재침전하여 목적 화합물인 [(9-ethyl-6-(1-(phenylcarbamoyloxyimino)ethyl)-carbazol)-3-yl](thiophen-2-yl)methanone을 1.7 g(수득률 = 86 %)로 얻었다.100 mL (9-ethyl-6- (1- (hydroxyimino) ethyl) -carbazol-3-yl) (thiophen-2-yl) methanone 1.5 g (4.1 mmol) and phenyl isocyanate 0.67 mL (6.2 mmol) was dissolved in 10 mL of dichloromethane and stirred. 0.1 g of dibutyltin dilaurate was added thereto and stirred for an additional 12 hours. After confirming that the reaction was completed by thin layer chromatography, the reaction product was extracted with dichloromethane / water and reprecipitated in n-hexane to obtain the target compound [(9-ethyl-6- (1- (phenylcarbamoyloxyimino) ethyl) -carbazol) -3 1.7 g (yield = 86%) of -yl] (thiophen-2-yl) methanone was obtained.

1H-NMR (δ, ppm, CDCl3) : 8.75 (s, 1H), 8.40-8.60 (m, 2H), 8.14 (d, 1H), 7.95 (d, 1H), 7.75 (t, 1H), 7.25-7.60 (m, 6H), 7.10-7.20 (m, 2H), 4.46 (q, 2H), 2.61 (s, 3H), 1.26 (t, 3H). 1 H-NMR (δ, ppm, CDCl 3 ): 8.75 (s, 1H), 8.40-8.60 (m, 2H), 8.14 (d, 1H), 7.95 (d, 1H), 7.75 (t, 1H), 7.25-7.60 (m, 6H), 7.10-7.20 (m, 2H), 4.46 (q, 2H), 2.61 (s, 3H), 1.26 (t, 3H).

[실시예 2-17]Example 2-17

실시예 2 내지 실시예 17의 화합물은 상응하는 출발 물질로부터 상기 실시예 1에 기술된 방법에 따라 제조하였다. 제조된 화합물들의 구조 및 1H-NMR 분석 결과를 하기 표 1 및 표 2에 각각 나타내었다.The compounds of Examples 2 to 17 were prepared according to the method described in Example 1 above from the corresponding starting materials. The structure of the prepared compounds and the results of 1 H-NMR analysis are shown in Tables 1 and 2, respectively.

[표 1]TABLE 1

Figure 112007052243254-PAT00023
Figure 112007052243254-PAT00023

Figure 112007052243254-PAT00024
Figure 112007052243254-PAT00024

[표 2]TABLE 2

Figure 112007052243254-PAT00025
Figure 112007052243254-PAT00025

Figure 112007052243254-PAT00026
Figure 112007052243254-PAT00026

Claims (6)

하기 화학식 1로 표시되는 옥심 카바메이트 화합물.An oxime carbamate compound represented by the following formula (1). [화학식 1][Formula 1]
Figure 112007052243254-PAT00027
Figure 112007052243254-PAT00027
 [상기 화학식 1에서, [In Formula 1, R1은 (C6-C30)아릴 또는 (C6-C30)헤테로아릴이고;R 1 is (C 6 -C 30 ) aryl or (C 6 -C 30 ) heteroaryl; 상기 R1의 아릴 또는 헤테로아릴은 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, 산소, 질소 또는 황을 포함하는 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C1-C12)알콕시, (C1-C12)알콕시(C1-C12)알킬, (C3-C8)시클로알킬, (C3-C8)시클로알킬(C1-C12)알킬, 산소, 질소 또는 황을 헤테로고리 안에 포함하는 3원 내지 7원의 포화 또는 불포화 헤테로시클로알킬, 산소, 질소 또는 황을 헤테로고리 안에 포함하는 3원 내지 7원의 포화 또는 불포화 헤테로시클로알킬(C1-C12)알킬, 히드록시(C1-C12)알킬, (C3-C8)시클로알킬(C1-C12)알콕시, (C1-C12)알킬카르보닐, (C1-C12)알콕시카르보닐, (C1-C12)알콕시카르보닐(C1-C12)알킬카르보닐, (C1-C12)알킬카르보닐옥시, (C6-C30)아릴, (C6-C30)헤테로아릴, (C6-C30)아릴카르보닐, (C6-C30)헤테로아릴카르보닐, (C6-C30)아릴티오, (C6-C30)헤테로아릴티오, 카르복실산, (C6-C30)헤테로아릴카르보닐(C6-C30)아릴티오, 할로겐, (C6-C30)아릴옥시, (C6-C30)아릴옥시카르보닐, (C6-C30)아릴옥시카르보닐(C1-C12)알킬카르보닐, (C6-C30)헤테로아릴옥시, (C6-C30)헤테로아릴옥시카르보닐, (C6-C30)헤테로아릴옥시카르보닐(C1-C12)알킬카르보닐, 히드록시, 시아노, 니트로, 트리(C1-C12)알킬실록시, 모노 또는 디 (C1-C12)알킬아미노카르보닐, 아미노카르보닐, -O(CH2CH2O)nH, -SR11, -SOR12, -SO2R13 및 -NR14R15로부터 선택된 하나이상의 치환기로 더 치환될 수 있고, R1과 R2는 (C1-C3)알킬렌 또는 (C2-C4)알케닐렌으로 연결되어 고리를 형성할 수 있으며;Aryl or heteroaryl of said R 1 is a saturated or unsaturated straight-chain or grinding (C 1 -C 12) alkyl, oxygen, nitrogen or sulfur, or a saturated or unsaturated straight chain of grinding comprising the (C 1 -C 12) alkyl, ( C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkoxy (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkyl (C 1 -C 12 3-7 membered saturated or unsaturated heterocycloalkyl containing alkyl, oxygen, nitrogen or sulfur in the heterocycle 3-7 membered saturated or unsaturated heterocycloalkyl comprising oxygen, nitrogen or sulfur in the heterocycle (C 1 -C 12 ) alkyl, hydroxy (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl (C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkylcarbonyl, ( C 1 -C 12 ) alkoxycarbonyl, (C 1 -C 12 ) alkoxycarbonyl (C 1 -C 12 ) alkylcarbonyl, (C 1 -C 12 ) alkylcarbonyloxy, (C 6 -C 30 ) aryl, (C 6 -C 30) heteroaryl, (C 6 -C 30) arylcarbonyl, (C 6 -C 30) H. Loa reel-carbonyl, (C 6 -C 30) arylthio, (C 6 -C 30) heteroaryl, alkylthio, carboxyl, (C 6 -C 30) heteroaryl, carbonyl (C 6 -C 30) arylthio , Halogen, (C 6 -C 30 ) aryloxy, (C 6 -C 30 ) aryloxycarbonyl, (C 6 -C 30 ) aryloxycarbonyl (C 1 -C 12 ) alkylcarbonyl, (C 6 -C 30 ) heteroaryloxy, (C 6 -C 30 ) heteroaryloxycarbonyl, (C 6 -C 30 ) heteroaryloxycarbonyl (C 1 -C 12 ) alkylcarbonyl, hydroxy, cyano, Nitro, tri (C 1 -C 12 ) alkylsiloxy, mono or di (C 1 -C 12 ) alkylaminocarbonyl, aminocarbonyl, -O (CH 2 CH 2 O) n H, -SR 11 ,- May be further substituted with one or more substituents selected from SOR 12 , -SO 2 R 13 and -NR 14 R 15 , wherein R 1 and R 2 are (C 1 -C 3 ) alkylene or (C 2 -C 4 ) alke May be linked to niylene to form a ring; R2 및 R3는 서로 독립적으로 수소, 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C3-C8)시클로알킬, (C1-C12)알콕시, (C1-C12)알킬티오, (C6-C30)아릴, (C6-C30)아르(C1-C12)알킬, (C1-C30)알킬(C6-C30)아릴, (C1-C30)알킬카르보닐, (C1-C12)알콕시카르보닐, (C1-C12)알킬카르보닐옥시, (C6-C30)아르(C1-C12)알킬카르보닐, (C6-C30)아르(C1-C12)알콕시카르보닐, (C6-C30)아르(C1-C12)알킬카르보닐옥시, (C6-C30)아르(C1-C12)알콕시, (C6-C30)아르(C1-C12)알킬티오 또는 메타아크릴레이트(methacrylate)이고, 상기 R2 및 R3의 알킬 또는 아릴기는 (C1-C12)알킬카르보닐, (C1-C12)알킬카르보 닐옥시, (C1-C12)알콕시카르보닐, (C1-C12)알콕시, (C1-C12)알킬티오, 트리(C1-C12)알킬실릴, 트리(C1-C12)알콕시실릴 또는 트리(C6-C30)아릴실릴로 더 치환될 수 있으며; R 2 and R 3 independently of one another are hydrogen, straight or branched saturated or unsaturated (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 1 -C 12 ) alkoxy, (C 1- C 12 ) alkylthio, (C 6 -C 30 ) aryl, (C 6 -C 30 ) ar (C 1 -C 12 ) alkyl, (C 1 -C 30 ) alkyl (C 6 -C 30 ) aryl, ( C 1 -C 30 ) alkylcarbonyl, (C 1 -C 12 ) alkoxycarbonyl, (C 1 -C 12 ) alkylcarbonyloxy, (C 6 -C 30 ) ar (C 1 -C 12 ) alkylcarbon carbonyl, (C 6 -C 30) ar (C 1 -C 12) alkoxycarbonyl, (C 6 -C 30) ar (C 1 -C 12) alkylcarbonyloxy, (C 6 -C 30) ar ( C 1 -C 12 ) alkoxy, (C 6 -C 30 ) ar (C 1 -C 12 ) alkylthio or methacrylate, wherein the alkyl or aryl group of R 2 and R 3 is (C 1 -C 12 ) alkylcarbonyl, (C 1 -C 12 ) alkylcarbonyloxy, (C 1 -C 12 ) alkoxycarbonyl, (C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkylthio, tri (C 1 -C 12 ) alkylsilyl, tri (C 1 -C 12 ) alkoxysilyl or tri (C 6 -C 30 ) arylsilyl May be further substituted; R11, R12, R13, R14 및 R15는 서로 독립적으로 수소, 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C3-C8)시클로알킬, (C1-C12)알킬카르보닐, (C6-C30)아릴 또는 트리(C1-C12)알킬실록시이며;R 11 , R 12 , R 13 , R 14 and R 15 independently of one another are hydrogen, straight or branched saturated or unsaturated (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 1- C 12 ) alkylcarbonyl, (C 6 -C 30 ) aryl or tri (C 1 -C 12 ) alkylsiloxy; m은 0 또는 1의 정수이고;m is an integer of 0 or 1; n은 1 내지 20의 정수이다.]n is an integer from 1 to 20.] 제 1항에 있어서,The method of claim 1, 하기 화학식 2 내지 4로부터 선택되는 것을 특징으로 하는 옥심 카바메이트 화합물.An oxime carbamate compound, characterized in that selected from the formulas (2) to (4). [화학식 2][Formula 2]
Figure 112007052243254-PAT00028
Figure 112007052243254-PAT00028
 [화학식 3][Formula 3]
Figure 112007052243254-PAT00029
Figure 112007052243254-PAT00029
 [화학식 4][Formula 4]
Figure 112007052243254-PAT00030
Figure 112007052243254-PAT00030
 [상기 화학식 2 내지 화학식 4에서,[In Formula 2 to Formula 4, A는 화학결합이거나
Figure 112007052243254-PAT00031
이며;A is a chemical bond
Figure 112007052243254-PAT00031
Is; B 및 D는 서로 독립적으로 O, S, CR41R42 또는 NR43이며;B and D are independently of each other O, S, CR 41 R 42 or NR 43 ; R2 및 R3는 청구항 제1항에서의 정의와 동일하며;R 2 and R 3 are the same as defined in claim 1; R21, R22, R23, R24, R25, R31, R32, R33, R34, R35, R36, R37, R38, R51, R52, R53, R54, R55, R56 및 R57은 서로 독립적으로 수소, 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, 산소, 질소 또는 황을 포함하는 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C1-C12)알콕시, (C1-C12)알콕시(C1-C12)알킬, (C3-C8)시클로알킬, (C3-C8)시클로알킬(C1-C12)알킬, 산소, 질소 또는 황을 헤테로고리 안에 포함하는 3원 내 지 7원의 포화 또는 불포화 헤테로시클로알킬, 산소, 질소 또는 황을 헤테로고리 안에 포함하는 3원 내지 7원의 포화 또는 불포화 헤테로시클로알킬(C1-C12)알킬, 히드록시(C1-C12)알킬, (C3-C8)시클로알킬(C1-C12)알콕시, (C1-C12)알킬카르보닐, (C1-C12)알콕시카르보닐, (C1-C12)알콕시카르보닐(C1-C12)알킬카르보닐, (C1-C12)알킬카르보닐옥시, (C6-C30)아릴, (C6-C30)헤테로아릴, (C6-C30)아릴카르보닐, (C6-C30)헤테로아릴카르보닐, (C6-C30)아릴티오, (C6-C30)헤테로아릴티오, 카르복실산, (C6-C30)헤테로아릴카르보닐(C6-C30)아릴티오, 할로겐, (C6-C30)아릴옥시, (C6-C30)아릴옥시카르보닐, (C6-C30)아릴옥시카르보닐(C1-C12)알킬카르보닐, (C6-C30)헤테로아릴옥시, (C6-C30)헤테로아릴옥시카르보닐, (C6-C30)헤테로아릴옥시카르보닐(C1-C12)알킬카르보닐, 히드록시, 시아노, 니트로, 트리(C1-C12)알킬실록시, 모노 또는 디 (C1-C12)알킬아미노카르보닐, 아미노카르보닐, -O(CH2CH2O)nH, -SR11, -SOR12, -SO2R13 또는 -NR14R15이거나, R21 내지 R25가 서로 인접한 R21 내지 R25와 (C1-C3)알킬렌 또는 (C2-C4)알케닐렌으로 결합하여 융합고리를 형성할 수 있거나 R2와 (C1-C3)알킬렌 또는 (C2-C4)알케닐렌으로 연결되어 고리를 형성할 수 있으며;R 21 , R 22 , R 23 , R 24 , R 25 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 51 , R 52 , R 53 , R 54 , R 55 , R 56 and R 57 are independently of each other hydrogen, straight or branched, saturated or unsaturated (C 1 -C 12 ) alkyl, straight or branched, saturated or unsaturated (C 1- C 12 ) alkyl, (C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkoxy (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) cycloalkyl 3- to 7-membered containing (C 1 -C 12 ) alkyl, oxygen, nitrogen or sulfur in the heterocycle 3- to 7-membered saturated or unsaturated heterocycloalkyl, oxygen, nitrogen or sulfur in the heterocycle Saturated or unsaturated heterocycloalkyl (C 1 -C 12 ) alkyl, hydroxy (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl (C 1 -C 12 ) alkoxy, (C 1 -C 12 ) alkylcarbonyl, (C 1 -C 12 ) alkoxycarbonyl, (C 1 -C 12 ) alkoxycarbonyl (C 1 -C 12 ) alkylcarbonyl, (C 1 -C 12 ) alkylcarbonyloxy, (C 6 -C 30 ) aryl, (C 6 -C 30 ) heteroaryl, (C 6 -C 30 ) arylcarbonyl, (C 6 -C 30 ) heteroarylcarbonyl, ( C 6 -C 30 ) arylthio, (C 6 -C 30 ) heteroarylthio, carboxylic acid, (C 6 -C 30 ) heteroarylcarbonyl (C 6 -C 30 ) arylthio, halogen, (C 6 -C 30 ) aryloxy, (C 6 -C 30 ) aryloxycarbonyl, (C 6 -C 30 ) aryloxycarbonyl (C 1 -C 12 ) alkylcarbonyl, (C 6 -C 30 ) heteroaryl Oxy, (C 6 -C 30 ) heteroaryloxycarbonyl, (C 6 -C 30 ) heteroaryloxycarbonyl (C 1 -C 12 ) alkylcarbonyl, hydroxy, cyano, nitro, tri (C 1 -C 12 ) alkylsiloxy, mono or di (C 1 -C 12 ) alkylaminocarbonyl, aminocarbonyl, -O (CH 2 CH 2 O) n H, -SR 11 , -SOR 12 , -SO 2 R 13 or —NR 14 R 15, or R 21 to R 25 are bonded to each other with R 21 to R 25 and (C 1 -C 3 ) alkylene or (C 2 -C 4 ) alkenylene to form a fused ring You can do it R2 and (C 1 -C 3) alkylene or (C 2 -C 4) alkenylene may form a ring; R11, R12, R13, R14, R15, R41, R42 및 R43는 서로 독립적으로 수소, 직쇄 또는 분쇄의 포화 또는 불포화 (C1-C12)알킬, (C3-C8)시클로알킬, (C1-C12)알킬카르보닐, (C6- C30)아릴 또는 트리(C1-C12)알킬실록시이며;R 11 , R 12 , R 13 , R 14 , R 15 , R 41 , R 42 and R 43 are independently of each other hydrogen, straight or branched, saturated or unsaturated (C 1 -C 12 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 1 -C 12 ) alkylcarbonyl, (C 6 -C 30 ) aryl or tri (C 1 -C 12 ) alkylsiloxy; m은 0 또는 1의 정수이고;m is an integer of 0 or 1; n은 1 내지 20의 정수이다.]n is an integer from 1 to 20.] 제 2항에 있어서,The method of claim 2, 하기 화학식 5 내지 8로부터 선택되는 것을 특징으로 하는 옥심 카바메이트 화합물.An oxime carbamate compound, characterized in that selected from the formula 5 to 8. [화학식 5][Formula 5]
Figure 112007052243254-PAT00032
Figure 112007052243254-PAT00032
 [화학식 6][Formula 6]
Figure 112007052243254-PAT00033
Figure 112007052243254-PAT00033
 [화학식 7][Formula 7]
Figure 112007052243254-PAT00034
Figure 112007052243254-PAT00034
 [화학식 8][Formula 8]
Figure 112007052243254-PAT00035
Figure 112007052243254-PAT00035
 [상기 화학식 5 내지 화학식 8에서,[In Formula 5 to Formula 8, R2 및 R3는 서로 독립적으로 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 펜틸, 헥실, 에틸헥실, 헵틸, 옥틸, 이소옥틸, 노닐, 메톡시, 에톡시, 프로폭시, 부톡시, 메틸티오, 에틸티오, 부틸티오, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 페닐, 비페닐, 나프틸, 안트릴, 플루오레닐, 벤질, 톨릴, 메타아크릴레이트(methacrylate), 트리메톡시실릴프로필, 트리에톡시실릴프로필 또는 트리페녹시실릴부틸이고;R 2 and R 3 independently of one another are hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, methoxy, ethoxy, propoxy, Butoxy, methylthio, ethylthio, butylthio, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, anthryl, fluorenyl, benzyl, tolyl, methacrylate, Trimethoxysilylpropyl, triethoxysilylpropyl or triphenoxysilylbutyl; R41, R42 및 R43은 서로 독립적으로 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 펜틸, 헥실, 에틸헥실, 헵틸, 옥틸, 이소옥틸, 노닐, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 페닐, 비페닐, 나프틸, 안트릴 또는 플루오레닐이고;R 41 , R 42 and R 43 independently of one another are hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, nonyl, cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, anthryl or fluorenyl; Z는 하기 구조의 아릴 또는 헤테로아릴이며;Z is aryl or heteroaryl of the structure:
Figure 112007052243254-PAT00036
Figure 112007052243254-PAT00036
 E는 N 또는 NO이고; F는 CH 또는 N이고; G는 CH 또는 N이고; H는 S, O 또는 NH이고; I는 CH 또는 N이고; J는 CH 또는 N이고; Q는 S, O 또는 NH이고; R는 CH 또는 N이고; W는 CH, N 또는 NO이고;E is N or NO; F is CH or N; G is CH or N; H is S, O or NH; I is CH or N; J is CH or N; Q is S, O or NH; R is CH or N; W is CH, N or NO; m은 0 또는 1의 정수이다.]m is an integer of 0 or 1.] 제 3항에 있어서,The method of claim 3, wherein 하기 화합물로부터 선택되는 것을 특징으로 하는 옥심 카바메이트 화합물.An oxime carbamate compound, characterized in that it is selected from the following compounds.
Figure 112007052243254-PAT00037
Figure 112007052243254-PAT00037
Figure 112007052243254-PAT00038
Figure 112007052243254-PAT00038
Figure 112007052243254-PAT00039
Figure 112007052243254-PAT00039
Figure 112007052243254-PAT00040
Figure 112007052243254-PAT00040
Figure 112007052243254-PAT00041
Figure 112007052243254-PAT00041
Figure 112007052243254-PAT00042
Figure 112007052243254-PAT00042
Figure 112007052243254-PAT00043
Figure 112007052243254-PAT00043
Figure 112007052243254-PAT00044
Figure 112007052243254-PAT00044
Figure 112007052243254-PAT00045
Figure 112007052243254-PAT00045
 제 1항 내지 제 4항에서 선택되는 어느 한 항에 따른 옥심 카바메이트 화합물을 유효성분으로 하는 광중합 개시제.A photopolymerization initiator comprising as an active ingredient an oxime carbamate compound according to any one of claims 1 to 4. 제 1항 내지 제 4항에서 선택되는 어느 한 항에 따른 옥심 카바메이트 화합물을 포함하는 광중합성 조성물.A photopolymerizable composition comprising the oxime carbamate compound according to any one of claims 1 to 4.
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