CN101805281A - 肟酯化合物和使用它们的感光性树脂组合物 - Google Patents
肟酯化合物和使用它们的感光性树脂组合物 Download PDFInfo
- Publication number
- CN101805281A CN101805281A CN200910266593A CN200910266593A CN101805281A CN 101805281 A CN101805281 A CN 101805281A CN 200910266593 A CN200910266593 A CN 200910266593A CN 200910266593 A CN200910266593 A CN 200910266593A CN 101805281 A CN101805281 A CN 101805281A
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- China
- Prior art keywords
- oxime ester
- photosensitive polymer
- compound
- ester compound
- photoepolymerizationinitiater initiater
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 Oxime ester compound Chemical class 0.000 title claims abstract description 36
- 229920000642 polymer Polymers 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims 1
- 239000003999 initiator Substances 0.000 abstract 2
- 239000011342 resin composition Substances 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000004304 visual acuity Effects 0.000 description 4
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- YLCILCNDLBSOIO-UHFFFAOYSA-N (3-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC(OC(=O)C=C)=C1 YLCILCNDLBSOIO-UHFFFAOYSA-N 0.000 description 1
- NQBWNECTZUOWID-UHFFFAOYSA-N (E)-cinnamyl (E)-cinnamate Natural products C=1C=CC=CC=1C=CC(=O)OCC=CC1=CC=CC=C1 NQBWNECTZUOWID-UHFFFAOYSA-N 0.000 description 1
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical group CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- YXNXCFZIHNRZOT-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;2-methylprop-2-enoic acid;terephthalic acid Chemical compound CC(=C)C(O)=O.OCC(CO)(CO)CO.OC(=O)C1=CC=C(C(O)=O)C=C1 YXNXCFZIHNRZOT-UHFFFAOYSA-N 0.000 description 1
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- JVCBVNUOEFLXGK-UHFFFAOYSA-N 2-(2-methoxyphenyl)-1h-imidazole Chemical class COC1=CC=CC=C1C1=NC=CN1 JVCBVNUOEFLXGK-UHFFFAOYSA-N 0.000 description 1
- XIOGJAPOAUEYJO-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4,5-diphenyl-1h-imidazole Chemical compound COC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 XIOGJAPOAUEYJO-UHFFFAOYSA-N 0.000 description 1
- SNFCQJAJPFWBDJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,5-diphenyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 SNFCQJAJPFWBDJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- QAGHEHQMRFEQMB-UHFFFAOYSA-N 2-ethylidenepropanedioic acid Chemical compound CC=C(C(O)=O)C(O)=O QAGHEHQMRFEQMB-UHFFFAOYSA-N 0.000 description 1
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- KORJZGKNZUDLII-UHFFFAOYSA-N 9-(4-methylphenyl)acridine Chemical compound C1=CC(C)=CC=C1C1=C(C=CC=C2)C2=NC2=CC=CC=C12 KORJZGKNZUDLII-UHFFFAOYSA-N 0.000 description 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical class C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
- MTRFEWTWIPAXLG-UHFFFAOYSA-N 9-phenylacridine Chemical compound C1=CC=CC=C1C1=C(C=CC=C2)C2=NC2=CC=CC=C12 MTRFEWTWIPAXLG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HJIYHOVBJRVELV-UHFFFAOYSA-N C(C)OCC(=S)OCCO Chemical compound C(C)OCC(=S)OCCO HJIYHOVBJRVELV-UHFFFAOYSA-N 0.000 description 1
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- CSCGRSSBEBRMOA-UHFFFAOYSA-N ClOC1=C(C=CC=C1)C=1NC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound ClOC1=C(C=CC=C1)C=1NC(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1 CSCGRSSBEBRMOA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
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- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
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- CKDJMJKKDIIJNA-UHFFFAOYSA-N [3-(2-methylprop-2-enoyloxy)phenyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC(OC(=O)C(C)=C)=C1 CKDJMJKKDIIJNA-UHFFFAOYSA-N 0.000 description 1
- ZCZFEIZSYJAXKS-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COC(=O)C=C ZCZFEIZSYJAXKS-UHFFFAOYSA-N 0.000 description 1
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供高敏感性的肟酯化合物作为感光性树脂组合物的光聚合引发剂。将下述通式(I)所示的(式中，各符号如说明书所定义)肟酯化合物作为感光性树脂组合物的光聚合引发剂使用。
Description
技术领域
本发明涉及新型的肟酯化合物和使用这些化合物的光聚合引发剂，以及含有这些化合物作为光聚合引发剂的感光性树脂组合物。
背景技术
感光性树脂组合物主要包含具有烯键式不饱和键的聚合性化合物和光聚合引发剂，烯键式不饱和化合物通常可以通过进行紫外线照射而固化。
为了聚合固化，必需的是与之适合的光聚合引发剂，通过进行紫外线照射，使得光聚合引发剂产生活性自由基，烯键式不饱和化合物发生反应而聚合。
根据聚合，作为用于得到微细线路等的光源，主要使用365nm或405nm的光。并且，由于通过使用对短波长光源具有敏感性的感光性树脂组合物，可以进行微细印刷等，故特别期待对365nm、405nm的光源具有优异敏感性的光聚合引发剂。
这些对短波长的光源具有敏感性的感光性树脂组合物可以在光固化性油墨、感光性印刷版、干膜抗蚀剂(ドライフイルムレジスト)、滤色器等各种领域中使用。
专利文献1～4中记载了肟酯衍生物，已知这些肟酯衍生物可以用作光聚合引发剂。
另外，在专利文献5和6中，记载了敏感性更高的O-酰基肟光引发剂。但是，这些O-酰基肟光引发剂作为以365nm、405nm为光源的光聚合引发剂，仍无法满足要求，更高敏感性的光聚合引发剂受到期待。
专利文献：
专利文献1：美国专利第3558309号说明书
专利文献2：美国专利第4255513号说明书
专利文献3：美国专利第4590145号说明书
专利文献4：美国专利第4202697号说明书
专利文献5：日本特开2000-80068号公报
专利文献6：日本特开2001-233842号公报
发明内容
迄今为止的肟酯系光聚合引发剂在365nm和405nm没有大的吸收，不能充分地得到所需要的敏感性，所以本发明是为了解决该问题而进行的。
因此，本发明的目的在于得到与现有的光聚合引发剂相比，在365nm和405nm处具有更大的光吸收能力，且敏感性高的光聚合引发剂，以及得到含有该光聚合引发剂的感光性树脂组合物。
本发明通过提供含有下述通式(I)所示的新型肟酯化合物和含有该化合物的光聚合引发剂，而实现上述目的。
本发明涉及通式(I)所示的肟酯化合物，使用该化合物的光聚合引发剂，以及含有其的感光性树脂组合物；
(式中，R1、R2分别表示甲基、乙基，R3表示甲基、苯基，Ar表示键或亚苯基、亚萘基、亚噻吩基)。
本发明的肟酯化合物的感光性、分辨力(解像性)、经时稳定性优异，特别是365nm和405nm处的吸光度比迄今为止的更高，有利于用作使用i线为光源的光聚合引发剂、或用作感光性树脂组合物。
具体实施方式
以下，对本发明的肟酯化合物、使用该化合物的光聚合引发剂、以及含有其的感光性树脂组合物进行详细说明。
本发明的上述通式(I)所示的化合物，特别是以下述为特征的化合物，即，式中R1、R2分别表示甲基、乙基，R3表示甲基、苯基，Ar表示键、亚苯基、亚萘基、亚噻吩基。
此外，在本发明的肟酯化合物中，从得到良好的感光性、分辨力、经时稳定性方面出发，上述通式(I)中特别优选R1具有乙基，R2具有甲基，R3具有甲基，Ar具有亚苯基、亚噻吩基的化合物。
为了得到作为本发明的中间体的肟，通常以下所示的反应是理想的。
可以将醛或酮与盐酸羟胺，在如醋酸钠或吡啶的碱的存在下，在如乙醇的极性溶剂中进行反应而合成。
上述通式(I)所示的本发明的肟酯化合物通常可以如下制备。
首先，将下述通式(II)所示的咔唑系化合物，
(R1表示甲基、乙基)
和下述通式(III)、
(Ar表示键、亚苯基、亚萘基、亚噻吩基)
以及下述通式(IV)所示的酰氯化物，
(R2表示甲基、乙基)
在如氯化铝的金属氯化物的存在下反应，得到下述通式(V)所示的酰化物，
(式中，R1、R2、Ar如上述所定义)。
接着，通过将上述通式(V)在盐酸羟胺、吡啶等碱的存在下进行反应，得到下述通式(VI所示的肟化合物，
(式中，R1、R2、Ar如上述所定义)。
接着，使上述通式(VI)和下述通式(VII)所示的酰氯化物等反应，
(R3表示甲基、乙基)
得到下述通式(I)所示的本发明的肟酯化合物，
(式中，R1、R2、R3、Ar如上述所定义)。
本发明的肟酯化合物适合用作具有能够自由基聚合的烯键式不饱和键的化合物的光聚合引发剂。
接着，对本发明的感光性树脂组合物进行说明。
感光性树脂组合物是在具有烯键式不饱和键的化合物、粘合剂等中含有本发明的光聚合引发剂而成的成分。另外，根据需要，可以通过混合热聚合抑制剂或者增塑剂等添加剂而调制。
作为本发明的具有烯键式不饱和双键的化合物，可以列举出例如不饱和羧酸、不饱和羧酸与脂肪族多羟基化合物的酯、不饱和羧酸与芳香族多羟基化合物的酯、由不饱和羧酸和多元羧酸以及多羟基化合物的酯化反应得到的酯等。
作为本发明的不饱和羧酸与脂肪族多羟基化合物的酯，可以列举出例如乙二醇二丙烯酸酯、三甘醇二丙烯酸酯、三羟甲基乙烷三丙烯酸酯、三羟甲基丙烷三丙烯酸酯、季戊四醇二丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、二季戊四醇四丙烯酸酯、二季戊四醇五丙烯酸酯、二季戊四醇六丙烯酸酯、甘油丙烯酸酯等丙烯酸酯，三甘醇二甲基丙烯酸酯、三羟甲基乙烷三甲基丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、季戊四醇二甲基丙烯酸酯、季戊四醇三甲基丙烯酸酯、季戊四醇四甲基丙烯酸酯、二季戊四醇二甲基丙烯酸酯、二季戊四醇三甲基丙烯酸酯、二季戊四醇四甲基丙烯酸酯等甲基丙烯酸酯，脂肪族多羟基化合物的衣康酸酯、巴豆酸酯、马来酸酯等。
作为本发明的不饱和羧酸与芳香族多羟基化合物的酯，可以列举出例如氢醌二丙烯酸酯、氢醌二甲基丙烯酸酯、间苯二酚二丙烯酸酯、间苯二酚二甲基丙烯酸酯等。
作为由不饱和羧酸与多元羧酸、多羟基化合物的酯化反应得到的酯，可以列举出例如丙烯酸-邻苯二甲酸-乙二醇的缩合物、丙烯酸-马来酸-二甘醇的缩合物、甲基丙烯酸-对苯二甲酸-季戊四醇的缩合物、丙烯酸-己二酸-丁二醇-甘油的缩合物等。
作为本发明中使用的具有烯键式不饱和双键的化合物的其它例子，可以列举亚乙基双丙烯酰胺等丙烯酰胺类、邻苯二甲酸二烯丙基酯等烯丙基酯、邻苯二甲酸二乙烯基酯等含乙烯基的化合物等。作为在主链具有烯键式不饱和双键的聚合物，可以列举出例如由不饱和二元羧酸与二羟基化合物的缩聚反应得到的聚酯、由不饱和二元羧酸与二胺的缩聚反应得到的聚酰胺等。
作为本发明的在侧链具有烯键式不饱和双键的聚合物，可以列举出在侧链具有不饱和键的二元羧酸，例如衣康酸、亚丙基琥珀酸、亚乙基丙二酸等与二羟基或二胺化合物的缩聚物等。另外，还可以使用侧链具有羟基和卤代甲基这样的官能团的聚合物，例如聚乙烯醇、聚(甲基丙烯酸2-羟乙基酯)、环氧树脂、苯氧树脂、聚环氧氯丙烷等与丙烯酸、甲基丙烯酸、巴豆酸这样的不饱和羧酸通过高分子反应得到的聚合物。
粘合剂可以通过将聚合性单体进行自由基聚合而得到。作为单体，可以列举出苯乙烯、乙烯基甲苯、α-甲基苯乙烯、对-甲基苯乙烯、对-乙基苯乙烯等苯乙烯衍生物，丙烯酰胺、丙烯腈等乙烯醇酯类，甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丙酯、甲基丙烯酸丁酯、甲基丙烯酸戊酯、甲基丙烯酸己酯等甲基丙烯酸烷基酯类，马来酸、马来酸酐、肉桂酸、衣康酸、巴豆酸等。
本发明的粘合剂的用量，相对于100重量份烯键式化合物，是30～1000重量份，更优选为50～150重量份。
另外，本发明肟酯化合物可以和下述所示公知的光聚合引发剂一起使用。
作为这些光聚合引发剂，可以列举出例如苯乙酮、二苯甲酮、4，4’-双(二乙基氨基)二苯甲酮、4-(甲基苯硫基)苯基苯基酮、苯偶酰二甲基缩酮、2-甲基-1-甲基硫代苯基-2-吗啉代丙烷-1-酮、2-苯偶酰(ベンジル)-2-二甲基氨基-1-(4-吗啉代苯基)丁烷-1-酮、对-二乙基氨基苯甲酸乙酯、噻吨酮、2，5-二乙基噻吨酮、2-氯咕吨酮、异丙基噻吨酮、1-氯-4-丙氧基-噻吨酮、2-(邻氯苯基)-4，5-二苯基咪唑二聚物、2-(邻氟苯基)-4，5-二苯基咪唑二聚物、2-(邻甲氧基苯基)-4，5-二苯基咪唑二聚物、2-(对甲氧基苯基)-4，5-二苯基咪唑二聚物、2-(邻氯苯基)-4，5-二(邻甲氧基苯基)咪唑二聚物、9-苯基吖啶、9-(对甲苯基)吖啶、1，7-双(9，9’-吖啶基)庚烷、N-苯基甘氨酸、双(η5-环戊二烯基)双[2，6-二氟-3-(1H-吡咯-1-基)苯基]钛、2-乙基蒽醌、1-氯蒽醌、2-苯基-4，6-双(三氯甲基)-均三嗪、2-(4-甲氧基苯基)-4，6-双(三氯甲基)-均三嗪、2-萘基-4，6-双(三氯甲基)-均三嗪、2-(4-甲氧基萘基)-4，6-双(三氯甲基)-均三嗪、2-甲基-4，6-双(三氯甲基)-均三嗪等。
本发明的感光性树脂组合物通常将肟酯化合物、具有烯键式不饱和键的聚合性化合物溶解或分散使用。
作为使用的溶剂，例如可以加入丙酮、甲乙酮、甲基异丁基酮、甲基戊基酮、乙二醇单甲基醚、乙二醇单乙基醚、乙二醇单丙基醚、乙二醇单丁基醚、二甘醇单甲基醚、二甘醇单乙基醚、二甘醇单丙基醚、乙二醇二甲基醚、乙二醇二乙基醚、二乙基醚、叔丁基甲基醚、叔丁基乙基醚、己烷、庚烷、辛烷、环己烷、苯、甲苯、二甲苯、甲醇、乙醇、异丙醇、1-丁醇、氯仿、N，N’-二甲基甲酰胺、N-甲基-2-吡咯烷酮等形成溶液状组合物使用。
本发明的感光性树脂组合物可以在各种印刷油墨、印刷版、涂料、粘合剂、干膜抗蚀剂、滤色器等用途中广泛使用，其用途没有特别的限定。
另外，作为本发明的曝光中使用的光源，可以使用卤素灯、氙灯、钨灯、金属卤化物灯、超高压水银灯、高压水银灯、中压水银灯、低压水银灯、发光二极管、激光二极管、F2准分子激光、KrF准分子激光、ArF准分子激光等。
在本发明的感光性树脂组合物中，光聚合引发剂的添加量没有特别的限定，相对于100重量份具有烯键式不饱和键的上述聚合性化合物，本发明的肟酯化合物通常为0.1～50重量份，考虑到敏感性和分辨率(解像度)等方面，更优选为1～40重量份。
接着，例示使用本发明的肟酯化合物的实施例，但是本发明并不受到下述实施例的限定。
实施例
[实施例1]肟酯化合物的合成
a.咔唑衍生物(酰化物)的合成
在40ml含5.00份N-乙基咔唑的CH2Cl2中，加入2.73份对苯二甲酰氯和3.76份AlCl3。在室温下搅拌一晚后，加入2.21份乙酰氯和3.76份AlCl3。将该反应混合物在室温下搅拌4小时。然后，将反应混合物注入冰水中。用乙酸乙酯萃取产物。用饱和NaHC03水溶液和食盐水洗涤乙酸乙酯层，之后，用无水硫酸镁干燥。浓缩溶剂后，得到5.91份(76.3％)淡黄绿色固体。该固体不精制而直接用于之后的反应。
b.肟体的合成
在30ml含3.0份a.中得到的酰化物的乙醇中，加入0.76份氯化羟基铵和0.86份吡啶。回流10小时后，将反应混合物注入冰水中。滤取所得的固体，用水洗净，溶解于乙酸乙酯中。用无水硫酸镁干燥后，浓缩，得到2.80份(89％)淡黄白色固体。该固体不精制而直接用于之后的反应。
c.肟酯体的合成
将1.5份b.中得到的肟体溶解到25份DMF中。在该溶液中加入0.59份乙酰氯，然后，在10℃以下滴加0.78份三乙基胺。在室温下搅拌4小时后，将反应混合物注入水中，过滤析出的固体。过滤物使用CH2Cl2-己烷(2∶1)，通过硅胶柱色谱精制，得到1.05份(61.8％)淡黄色固体。λmax是345nm，熔点是191～202℃。
[实施例2～5]
通过相同的方法合成的下述通式(IX)所示的本发明的各种化合物的具体结构和测定结果如表1所示。
表1
[实施例6]感光性树脂组合物的制造
配合表2所示的材料，得到感光性树脂组合物。
表2
另外，在比较例1、2中，作为光聚合引发剂使用下述所示的市售品。
[比较例1]
商品名：OXE-01(Ciba Specialty Chemicals制造)
[比较例2]
商品名：OXE-02(Ciba Specialty Chemicals制造)
接着，在玻璃基板上，使用旋转涂布器，涂布上述表2所示的各种感光性树脂组合物以形成3μm的膜厚，在烘箱中、80℃下干燥3分钟。之后，使用超高压水银灯，改变曝光量，进行曝光。接着，在30℃下将1.0重量％碳酸钠水溶液喷雾3分钟，进行未曝光部分的除去。
实施例1～5和比较例1～2的结果如表3所示。
其中所示的敏感性是以依据尺寸可以形成25μm的抗蚀图案的曝光量表示的。
在表3中，虽然表示曝光量越少敏感性越高，但本发明的感光性树脂组合物与比较例的相比，显示出优异的敏感性和分辨率。
表3
| 敏感性(mJ/cm2) | |
| 实施例1 | 82 |
| 实施例2 | 86 |
| 实施例3 | 77 |
| 实施例4 | 75 |
| 实施例5 | 83 |
| 比较例1 | 250 |
| 比较例2 | 98 |
产业实用性
本发明的肟酯化合物和现有的相比，在365nm、405nm处的光吸收能力更优异。另外，以具有烯键式不饱和键的聚合性化合物与本发明的肟酯化合物作为光聚合引发剂的感光性树脂组合物，在上述波长区域具有优异的敏感性和分辨率、保存稳定性等。
而且，本发明的感光性树脂组合物通过进行上述波长区域的紫外线照射，使得光聚合引发剂产生活性自由基，烯键式不饱和化合物进行反应而有效地聚合，所以可以在光固化性油墨、感光性印刷版、干膜抗蚀剂、滤色器等各种领域中使用。
Claims (3)
1.下述通式(I)所示的肟酯化合物，
式中，R1、R2分别表示甲基、乙基，R3表示甲基、苯基，Ar表示键或亚苯基、亚萘基、亚噻吩基。
2.以权利要求1所述的肟酯化合物为有效成分的光聚合引发剂。
3.在具有烯键式不饱和键的聚合性化合物中含有权利要求2所述的光聚合引发剂而成的感光性树脂组合物。
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| CN104144912A (zh) * | 2012-03-22 | 2014-11-12 | 株式会社艾迪科 | 新型化合物以及感光性树脂组合物 |
| US9594302B2 (en) | 2012-03-22 | 2017-03-14 | Adeka Corporation | Compound and photosensitive resin composition |
| CN109153915A (zh) * | 2016-05-17 | 2019-01-04 | 默克专利股份有限公司 | 可聚合的液晶材料及经聚合的液晶膜 |
| CN109153915B (zh) * | 2016-05-17 | 2022-09-23 | 默克专利股份有限公司 | 可聚合的液晶材料及经聚合的液晶膜 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100093468A (ko) | 2010-08-25 |
| KR101618877B1 (ko) | 2016-05-09 |
| US8088836B2 (en) | 2012-01-03 |
| JP4344400B1 (ja) | 2009-10-14 |
| TWI406847B (zh) | 2013-09-01 |
| TW201031635A (en) | 2010-09-01 |
| US20100210749A1 (en) | 2010-08-19 |
| JP2010189279A (ja) | 2010-09-02 |
| CN101805281B (zh) | 2014-03-05 |
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