JP6725663B2 - フルオレン類多官能光開始剤およびその製造ならびに使用、フルオレン類光開始剤含有感光性樹脂組成物およびその使用 - Google Patents
フルオレン類多官能光開始剤およびその製造ならびに使用、フルオレン類光開始剤含有感光性樹脂組成物およびその使用 Download PDFInfo
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- JP6725663B2 JP6725663B2 JP2018530699A JP2018530699A JP6725663B2 JP 6725663 B2 JP6725663 B2 JP 6725663B2 JP 2018530699 A JP2018530699 A JP 2018530699A JP 2018530699 A JP2018530699 A JP 2018530699A JP 6725663 B2 JP6725663 B2 JP 6725663B2
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- alkyl group
- linear
- branched alkyl
- hydrogen atom
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- 239000011342 resin composition Substances 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 23
- 239000010408 film Substances 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- -1 fluorenes compound Chemical class 0.000 claims description 35
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 239000000543 intermediate Substances 0.000 claims description 27
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 239000002994 raw material Substances 0.000 claims description 15
- 229920002120 photoresistant polymer Polymers 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000003973 paint Substances 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 239000003086 colorant Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000006850 spacer group Chemical group 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 239000000976 ink Substances 0.000 claims description 8
- 238000000016 photochemical curing Methods 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 238000005893 bromination reaction Methods 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 238000005695 dehalogenation reaction Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000007806 chemical reaction intermediate Substances 0.000 claims description 4
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 241001553014 Myrsine salicina Species 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 238000010526 radical polymerization reaction Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
- 239000000203 mixture Substances 0.000 description 40
- 239000010410 layer Substances 0.000 description 35
- 239000000049 pigment Substances 0.000 description 30
- 229920001577 copolymer Polymers 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 206010034972 Photosensitivity reaction Diseases 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 238000013508 migration Methods 0.000 description 7
- 230000005012 migration Effects 0.000 description 7
- 230000036211 photosensitivity Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- 239000013067 intermediate product Substances 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 150000003384 small molecules Chemical class 0.000 description 6
- 238000012916 structural analysis Methods 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 238000004383 yellowing Methods 0.000 description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- 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 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 2
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
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- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 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
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
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- UZDMJPAQQFSMMV-UHFFFAOYSA-N 4-oxo-4-(2-prop-2-enoyloxyethoxy)butanoic acid Chemical compound OC(=O)CCC(=O)OCCOC(=O)C=C UZDMJPAQQFSMMV-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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000006231 channel black Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
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- 125000005549 heteroarylene group Chemical group 0.000 description 2
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- 150000002605 large molecules Chemical class 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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- 229910001507 metal halide Inorganic materials 0.000 description 2
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000001782 photodegradation Methods 0.000 description 2
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 239000001056 green pigment Substances 0.000 description 1
- USPLKTKSLPLUJG-UHFFFAOYSA-N hexan-2-yl 2-methylprop-2-enoate Chemical compound CCCCC(C)OC(=O)C(C)=C USPLKTKSLPLUJG-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- ZZXXBDPXXIDUBP-UHFFFAOYSA-N hydroxymethyl prop-2-enoate Chemical compound C(C=C)(=O)OCO.C(C=C)(=O)OCO ZZXXBDPXXIDUBP-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002469 indenes Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- VSQYNPJPULBZKU-UHFFFAOYSA-N mercury xenon Chemical compound [Xe].[Hg] VSQYNPJPULBZKU-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- ZZSKMNCIAKKVRB-UHFFFAOYSA-N morpholin-4-yl-(2-nitrophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)N1CCOCC1 ZZSKMNCIAKKVRB-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- BSCJIBOZTKGXQP-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCO BSCJIBOZTKGXQP-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RSVDRWTUCMTKBV-UHFFFAOYSA-N sbb057044 Chemical compound C12CC=CC2C2CC(OCCOC(=O)C=C)C1C2 RSVDRWTUCMTKBV-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
- C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/215—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/01—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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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
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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
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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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Optical Filters (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
好ましくはAは、水素原子、ニトロ基、又は−CO−CR2R3R4基を表す。−CO−CR2R3R4基である場合、R2、R3及びR4は上記と同じ定義を有する。
工程(1):フリーデルクラフト反応
三塩化アルミニウム又は塩化亜鉛の触媒作用下、原料aと原料bとを有機溶媒中でフリーデルクラフト反応させ、中間体aを得る。
溶媒が存在する条件下で中間体aを液体臭素と臭素化反応させ、中間体bを生成する。
中間体bを加水分解又は非水酸基光活性基含有化合物と反応させ、目標生成物を得る。
(A)ラジカル重合性化合物と、(B)光開始剤と、(C)任意に(optionally)、着色剤と、(D)任意に(optionally)、アルカリ可溶性樹脂とを含む感光性樹脂組成物。
<成分(A)ラジカル重合性化合物>
本発明の感光性樹脂組成物において、成分(A)は、ラジカル重合可能なエチレン性不飽和結合を有する化合物又は/及びエポキシ化合物である。いわゆる「ラジカル重合可能なエチレン性不飽和結合を有する化合物」は、分子中に少なくとも1個以上のラジカル重合可能なエチレン性不飽和結合を有する化合物であり、上記化合物は単量体、オリゴマー、ポリマー等の化学的形態を有してもよい。
本発明が使用している成分(B)光開始剤は、式(I)又は式(II)で表されるフルオレン類化合物及び式(I)又は式(II)で表される化合物を主構造とする誘導体化合物から選ばれる少なくとも1種である。当該光開始剤は、式(I)又は式(II)で表されるフルオレン類化合物あるいはそれを主構造とする誘導体化合物のみで構成されてもよいし、2種の化合物の組み合わせであってもよい。
さらに、本発明の感光性樹脂組成物は、成分(C)着色剤を含有してもよい。非限定的に、着色剤を含有することにより、本発明の組成物は、液晶ディスプレイのカラーフィルタの形成に使用可能である。かつ、遮光剤を着色剤とする場合、組成物は、表示装置のカラーフィルタにおけるブラックマトリックスイメージチューブの形成に使用可能である。
本発明の重合性組成物は、アルカリ可溶性樹脂と混合して併用してもよく、アルカリ可溶性樹脂(D)はバインダーとして機能すればよく、画像パターンを形成する際に、その現像処理工程において用いられる現像液は、好ましくは可溶性アルカリ性現像液であり、好ましくはカルボキシル基含有共重合体としてのアルカリ可溶性樹脂であり、特に好ましくは1個以上のカルボキシル基を有するエチレン性不飽和単量体(以下、単に「カルボキシル基含有不飽和単量体(P)」と呼ぶ)とその他の共重合可能なエチレン性不飽和単量体(以下、単に「共重合性不飽和単量体(Q)」と呼ぶ)との共重合体(以下、単に「カルボキシル基含有共重合体(R)」と呼ぶ)である。
成分(D)の感光性樹脂組成物における含有量は0〜80質量部であり、好ましくは20〜60質量部である。
生成物の応用要求に応じて、当該組成物には、さらに必要に応じて1種又は複数種の大分子又は高分子化合物を添加することで組成物の使用過程における応用性能を向上させてもよく、このような大分子又は高分子化合物は、ポリオール又はポリエステルポリオールであってもよく、反応官能基を含有しないポリマーを選択的に添加してもよく、これらのポリマーは、通常、フェノール性水酸基、水酸基等の酸性官能基を含有する樹脂であり、その他の光開始剤と組み合わせて使用してもよい。
各成分を秤量した後に均一に混合させ、本発明の感光性樹脂組成物が得られることは当業者にとって公知の慣例的な技術であり、本発明に記載の感光性組成物は、インク、塗料、バインダー等の普通の光硬化分野に使用可能であるのみならず、さらにハイエンド光硬化分野に使用可能であり、例えばカラーフィルタフィルム、フォトレジスト、ブラックマトリックス、フォトスペーサー、リブ、ウエットフィルム、ドライフィルムの製造に使用可能である。
実施例1
500mLの四つ口フラスコ中に97gの原料1aと、67gの三塩化アルミニウムと、100mLのジクロロメタンとを加え、氷水浴で0℃に降温し、54gの原料1b(すなわち、イソブタン酸クロリド)と50mLのジクロロメタンとの混合溶液を滴下し、10℃以下に温度制御し、約2hをかけて滴下終了し、滴下終了後に引き続いて2h攪拌し、反応が完全になるまで液体クロマトグラフィーによりトラッキングし、次いで、得られる材料を800gの氷水と100mLの濃塩酸(37%)とからなる希塩酸にゆっくりと注ぎ、加えながら攪拌し、その後、分液漏斗に注ぎ、下層、つまりジクロロメタン層を抜き出し、そして50mLのジクロロメタンで水層を引き続いて洗浄し、ジクロロメタン層と合併し、5%炭酸水素ナトリウム水溶液(300mL×3回)でジクロロメタン層を洗浄し、次いで、pHが中性となるまでジクロロメタン層を水洗浄し、150gの無水硫酸マグネシウムでジクロロメタン層を乾燥させ、濾過した後、ジクロロメタン生成物溶液を回転蒸発し、メタノールで再結晶させ、60℃のオーブンで2h乾燥させ、121gの中間体1aを得、収率が92%であり、純度が98%であった。
1H-NMR(CDCl3,500MHz):1.2146-1.3005(6H,d),1.6788(6H,s) ,3.3005-3.3994(1H,m) ,7.2881-8.0231(7H,m)。
MS(m/z):265(M+1)+ 。
500mLの四つ口フラスコ中に49gの中間体1aと、50mLのジクロロメタンとを加え、攪拌しながら40℃に昇温し、排気ガス吸収装置に接続し、16gの臭素を含有するジクロロメタン溶液を80mL滴下し、約2hをかけて滴下終了し、続いて温度保持して2h攪拌し、次いで、25%NaOH氷水溶液に注いで30min撹拌し、分液漏斗でジクロロメタン層を抜き出し、再度、50mLのジクロロメタンで水層を抽出し、ジクロロメタン層と合併し、中性となるまで水洗浄し、回転蒸発した後にメタノールで再結晶させ、60gの白色固体、すなわち、中間体1bを得、収率が86%であり、純度が98%であった。
1H-NMR(CDCl3,500MHz):1.6642(6H,s),2.0629 (6H,s),7.3080-7.8346(7H,m);
MS(m/z):344(M+1)+。
250mLの四つ口フラスコ中に34gの中間体1bと、50mLのジクロロエタンと、0.2gのテトラブチルアンモニウムブロマイドと、75gの、濃度が40%のNaOH水溶液とを加え、80℃で2h加熱還流し、反応が終了するまで液体クロマトグラフィーによりトラッキングし、次いで、室温に降温し、分液漏斗でジクロロエタン層を抜き出し、ジクロロエタン層が中性となるまで水洗浄し、回転蒸発してジクロロエタンを除去し、メタノールで再結晶させ、24gの白色固体生成物、すなわち、化合物1’を得、収率が87%であり、純度が99%であった。
1H-NMR(CDCl3,500MHz):1.5062(6H,s),1.6669 (6H,s),2.0755-2.2992(1H,s),7.2251-7.8325(7H,m)。MS(m/z):281M+1)+。
500mLの四つ口フラスコ中に106gの原料2aと、67gの三塩化アルミニウムと、100mLのジクロロメタンとを加え、氷水浴で0℃に降温し、54gのイソブタン酸クロリドと50mLのジクロロメタンとの混合溶液を滴下し、10℃以下に温度制御し、約2hをかけて滴下終了し、滴下終了後に引き続いて2h攪拌し、反応が完全になるまで液体クロマトグラフィーによりトラッキングし、次いで、得られる材料を、800gの氷水と100mLの濃塩酸とからなる希塩酸にゆっくりと注ぎ、加えながら攪拌し、その後、分液漏斗に注ぎ、下層、つまりジクロロメタン層を抜き出し、そして50mLのジクロロメタンで水層を引き続いて洗浄し、ジクロロメタン層と合併し、5%炭酸水素ナトリウム水溶液(300mL×3回)でジクロロメタン層を洗浄し、次いで、pHが中性となるまでジクロロメタン層を水洗浄し、150gの無水硫酸マグネシウムでジクロロメタン層を乾燥させ、濾過した後、ジクロロメタン生成物溶液を回転蒸発し、メタノールで再結晶させ、60℃のオーブンで2h乾燥させ、128gの中間体2aを得、収率が91%であり、純度が98%であった。
1H-NMR(CDCl3,500MHz):1.2007-1.2316(6H,d),3.3208-3.3447(1H,m),3.8676-3.8801(2H,s),7.9111-8.0352(6H,m)MS(m/z):282(M+1)+ 。
500mLの四つ口フラスコ中に56gの中間体2aと、50mLのジクロロメタンとを加え、攪拌しながら40℃に昇温し、排気ガス吸収装置に接続し、臭素16gの臭素を含有するジクロロメタン溶液を80mL滴下し、約2hをかけて滴下終了し、続いて温度保持して2h攪拌し、次いで25%NaOH氷水溶液中に注いで30min撹拌し、分液漏斗でジクロロメタン層を抜き出し、再度50mLのジクロロメタンで水層を抽出し、ジクロロメタン層と合併し、中性となるまで水洗浄し、回転蒸発した後にメタノールで再結晶させ、61gの白色固体、すなわち、中間体2bを得、収率が86%であり、純度が98%であった。
1H-NMR(CDCl3,500MHz):2.0632(6H,s),3.8679 (2H,s),7.9083-8.0956(6H,m)。
MS(m/z):361(M+1)+。
250mLの四つ口フラスコ中に36gの中間体2bと、60gのモルホリンとを加え、130℃で60h加熱還流し、反応が完全となるまで液体クロマトグラフィーによりトラッキングし、次いで、反応液を水中に注いで攪拌し、オフホワイト色の固体を析出し、吸引濾過し、水洗浄して、メタノールで再結晶させて22.3gの白色固体、すなわち、化合物2’を得、収率が60%であり、純度が99%であった。
1H-NMR(CDCl3,500MHz):1.3613(6H,s),2.3629-2.4101(4H,t),3.6765-3.7242(4H,t),3.8740 (2H,s),7.9225-8.4366(6H,m)。MS(m/z):367(M+1)+ 。
1000mLの四つ口フラスコ中に111gの原料3aと、134gの三塩化アルミニウムと、200mLのジクロロメタンとを加え、氷水浴で0℃に降温し、107gのイソブタン酸クロリドと100mLのジクロロメタンとの混合溶液を滴下し、10℃以下に温度制御し、約2hをかけて滴下終了し、滴下終了後に引き続いて2h攪拌し、反応が完全になるまで液体クロマトグラフィーによりトラッキングし、次いで、得られる材料を800gの氷水と150mLの濃塩酸とからなる希塩酸中にゆっくりと注ぎ、加えながら攪拌し、その後、分液漏斗に注ぎ、下層、つまりジクロロメタン層を抜き出し、100mLのジクロロメタンで引き続いて水層を洗浄し、ジクロロメタン層と合併し、5%炭酸水素ナトリウム水溶液(300mL×3回)でジクロロメタン層を洗浄し、次いで、pHが中性となるまでジクロロメタン層を水洗浄し、200gの無水硫酸マグネシウムでジクロロメタン層を乾燥させ、濾過後にジクロロメタン生成物溶液を回転蒸発し、メタノールで再結晶させ、60℃のオーブンで2h乾燥させ、163gの中間体3aを得、収率が90%であり、純度が98%であった。
1H-NMR(CDCl3,500MHz):0.9667-1.0002(6H,t),1.2149-1.2355(12H,d),1.9062-1.9147(2H,m),3.3265-3.4272(2H,m),7.9327-8.1753(6H,m)。
MS(m/z):363(M+1)+ 。
500mLの四つ口フラスコ中に73gの中間体3aと、80mLのジクロロメタンとを加え、攪拌しながら40℃に昇温し、排気ガス吸収装置に接続し、32gの臭素を含有するジクロロメタン溶液を100mL滴下し、約2hをかけて滴下終了し、続いて温度保持して2h攪拌し、次いで、25%のNaOH氷水溶液中に注いで30min撹拌し、分液漏斗でジクロロメタン層を抜き出し、再度80mLのジクロロメタンで水層を抽出して、ジクロロメタン層と合併し、中性となるまで水洗浄し、回転蒸発した後にメタノールで再結晶させ、87gの白色固体、すなわち、中間体3bを得、収率が84%であり、純度が98%であった。
1H-NMR(CDCl3,500MHz):0.9664(6H,t),1.8991-1.9132(4H,m),2.0632(12H,s),3.8679 (2H,s),7.9111-8.1506(6H,m)。
MS(m/z):521(M+1)+。
500mLの四つ口フラスコ中に52gの中間体3bと、100mLのジクロロエタンと、0.3gのテトラブチルアンモニウムブロマイドと、150gの濃度が40%のNaOH水溶液とを加え、80℃で2h加熱還流し、反応が終了するまで液体クロマトグラフィーによりトラッキングし、次いで、室温に降温し、分液漏斗でジクロロエタン層を抜き出し、ジクロロエタン層が中性となるまで水洗浄し、回転蒸発してジクロロエタンを除去し、メタノールで再結晶させ、33gの白色固体生成物、すなわち、化合物3’を得、収率が85%であり、純度が99%であった。
1H-NMR(CDCl3,500MHz):0.9599-0.9754(6H,t),1.4927(12H ,s),1.8976-1.9088 (4H,t),2.0146-2.1961(2H,s),7.91571-8.1677(6H,m)。MS(m/z):395(M+1)+。
実施例1〜3の方法を参照しながら、相応的な原料から下記表1で示している化合物4’〜14’を製造した。
典型的な光硬化樹脂組成物を調製することにより、本発明の式(I)で表される光開始剤の、光硬化性能、臭気性/マイグレーション性及び耐黄変性等の点を含む各項目の応用性能を評価し、具体的なステップは以下の通りである。
アクリレート共重合体 200質量部
[ベンジルメタクリレート/メタクリル酸/ヒドロキシエチルメタクリレート(モル比70/10/20)共重合体(Mv:10000)]
ジペンタエリスリトールヘキサアクリレート 100質量部
光開始剤 5質量部
ブタノン(溶媒) 900質量部
上記組成物において、光開始剤は本発明に開示の式(I)の化合物又は従来技術で既知されている光開始剤(比較例として)である。
上記組成物を黄光ランプ下で攪拌し、材料を取ってPETプレート上にローラーコーティングにより成膜し、90℃で2min乾燥させ、乾燥膜厚が2μmの塗膜を得、その後、室温に冷却し、高圧水銀ランプ(露光装置型番:RW−UV70201,露光量 150mJ/cm2)で照射して塗膜を露光し、硬化成膜させた。
表3で示している配合に従い、実施例20〜27及び比較例5〜8の感光性樹脂組成物を調製した。ただし、比較例5〜8における光開始剤A1〜A4の構造は下記の通りである。
マスク板を敷き、LED光源(UVATA LED UV硬化照射装置、最大照射強度が400mW/cm2)を用いて、マスク板の隙間を透過して波長370〜420nmの紫外線照射下で塗膜を露光した。
25℃の温度で、1%NaOH水溶液を用いて現像し、さらに超純水で洗浄し、風乾させた。
最後に、240℃のオーブン中で30minポストベークし、マスク板から転写したパターンを得た。
1.露光感度の評価
露光工程において光照射領域が現像後の残膜率が90%又はそれ以上である最小露光量を露光必要量と評価し、露光必要量が小さければ小さいほど感度が高いことを示す。
走査型電子顕微鏡(SEM)で基板上のパターンを観察し、現像性及びパターン完全性を評価する。
現像性を以下の基準で評価する。
GB/T 6739−1996『塗膜硬度の鉛筆測定法』を参照して評価を行った。塗膜鉛筆スクラッチ硬度試験器を用いて、塗膜のスクラッチ痕を観察し、スクラッチ痕が見られなかった鉛筆を塗膜の鉛筆硬度とした。
GB9286−88『塗料及びワニス塗膜のクロスカット試験』に参照して、クロスカット実験法により塗膜付着力の良否を評価した。破壊程度に基づき、0〜5級に分け(合計6つの等級)、その中、一番良いのは0級であり、膜面に格子の剥がれが一切見られず、5級は極めて悪く、膜面にひどい剥がれが発生した。
Claims (17)
- 下記式(I)で表される構造を有するフルオレン類多官能光開始剤。
R1は、それぞれ独立に水素原子、C1−C4の直鎖もしくは分岐アルキル基、又はC3−C6のシクロアルキル基でモノ置換されているC1−C3のアルキル基を表す。
R4は、N−モルホリニル基を表す。
Aは、水素原子、ニトロ基又は−CO−CR2R3R4基を表す。
R2及びR3は、互いに独立にC1−C10の直鎖もしくは分岐アルキル基、又はC4−C10のシクロアルキルアルキル基を表すか、あるいはR2及びR3は、互いに結合してC3−C10のシクロアルキル基を形成している。 - R1は、それぞれ独立に水素原子、C1−C4の直鎖もしくは分岐アルキル基、又はC3−C6のシクロアルキル基でモノ置換されているC1−C3のアルキル基を表す。
Aは、水素原子、ニトロ基又は−CO−CR2R3R4基を表す。
R2及びR3は、互いに独立にC1−C10の直鎖もしくは分岐アルキル基、又はC4−C10のシクロアルキルアルキル基を表すか、あるいはR2及びR3は、互いに結合してC3−C10のシクロアルキル基を形成している、請求項1に記載のフルオレン類多官能光開始剤。 - R1は、それぞれ独立にC1−C4の直鎖もしくは分岐アルキル基、又はC3−C6のシクロアルキル基でモノ置換されているC1−C3のアルキル基を表す。
Aは、水素原子、ニトロ基又は−CO−CR2R3R4基を表す。
R2及びR3は、互いに独立にC1−C4の直鎖もしくは分岐アルキル基、又はC4−C8のシクロアルキルアルキル基を表すか、あるいはR2及びR3は、互いに結合してC3−C6のシクロアルキル基を形成している、請求項1に記載のフルオレン類多官能光開始剤。 - R1は、それぞれ独立にC1−C4の直鎖もしくは分岐アルキル基を表す。
Aは、水素原子、ニトロ基又は−CO−CR2R3R4基を表す。
R2及びR3は、互いに独立にC1−C4の直鎖もしくは分岐アルキル基、又はC4−C8のシクロアルキルアルキル基を表すか、あるいはR2及びR3は、互いに結合してC3−C6のシクロアルキル基を形成している、請求項1に記載のフルオレン類多官能光開始剤。 - 下記の化合物のいずれかである、請求項1に記載のフルオレン類多官能光開始剤。
- (A)ラジカル重合反応に用いられる、エチレン性不飽和結合を有する化合物と、
(B)式(I)で表されるフルオレン類化合物のうちの少なくとも1種である光開始剤と、
(C)着色剤と、
を含むことを特徴とする感光性樹脂組成物。
R1は、それぞれ独立に水素原子、C1−C4の直鎖もしくは分岐アルキル基、又はC3−C6のシクロアルキル基でモノ置換されているC1−C3のアルキル基を表す。
R4は、水酸基、ジアルキルアミノ基又はN−モルホリニル基を表す。
Aは、水素原子、C1−C10の直鎖もしくは分岐アルキル基又はニトロ基を表す。
R2及びR3は、互いに独立にC1−C10の直鎖もしくは分岐アルキル基、又はC4−C10のシクロアルキルアルキル基を表すか、あるいはR2及びR3は、互いに結合して環を形成している。
ただし、
Aが水素原子を表し、かつR1がそれぞれ独立に水素原子又はC1−C4の直鎖もしくは分岐アルキル基を表す場合、R4は、N−モルホリニル基を表す。
AがC1−C10の直鎖もしくは分岐アルキル基を表し、かつR4がジアルキルアミノ基を表す場合、R2及びR3は、互いに結合して環を形成している。 - R1は、それぞれ独立に水素原子、C1−C4の直鎖もしくは分岐アルキル基、又はC3−C6のシクロアルキル基でモノ置換されているC1−C3のアルキル基を表す。
R4は、N−モルホリニル基を表す。
Aは、水素原子、C1−C10の直鎖もしくは分岐アルキル基又はニトロ基を表す。
R2及びR3は、互いに独立にC1−C10の直鎖もしくは分岐アルキル基、又はC4−C10のシクロアルキルアルキル基を表すか、あるいはR2及びR3は、互いに結合して環を形成している、請求項6に記載の感光性樹脂組成物。 - R1は、それぞれ独立にC1−C4の直鎖もしくは分岐アルキル基、又はC3−C6のシクロアルキル基でモノ置換されているC1−C3のアルキル基を表す。
R4は、N−モルホリニル基を表す。
Aは、水素原子又はニトロ基を表す。
R2及びR3は、互いに独立にC1−C4の直鎖もしくは分岐アルキル基、又はC4−C8のシクロアルキルアルキル基を表すか、あるいはR2及びR3は、互いに結合して環を形成している、請求項6に記載の感光性樹脂組成物。 - R1は、それぞれ独立にC1−C4の直鎖もしくは分岐アルキル基を表す。
R4は、N−モルホリニル基を表す。
Aは、水素原子又はニトロ基を表す。
R2及びR3は、互いに独立にC1−C4の直鎖もしくは分岐アルキル基、又はC4−C8のシクロアルキルアルキル基を表すか、あるいはR2及びR3は、互いに結合して環を形成している、請求項6に記載の感光性樹脂組成物。 - 式(I)で表されるフルオレン類化合物が以下の化合物であることを特徴とする請求項6に記載の感光性樹脂組成物。
- アルカリ可溶性樹脂(D)をさらに含有することを特徴とする請求項6に記載の感光性樹脂組成物。
- 請求項1〜5のいずれか1項に記載のフルオレン類多官能光開始剤又は請求項6〜11のいずれか1項に記載の感光性樹脂組成物の、光硬化分野への使用。
- カラーフィルタフィルム、フォトレジスト、ブラックマトリックス、フォトスペーサー、リブ、ウエットフィルム、ドライフィルム、インク、塗料及びバインダーの製造への使用であることを特徴とする請求項12に記載の使用。
- 請求項1〜5のいずれか1項に記載のフルオレン類多官能光開始剤の製造方法であって、下記の工程を含む製造方法。
工程(1):フリーデルクラフト反応
三塩化アルミニウム又は塩化亜鉛の触媒作用下、原料aと原料bとを有機溶媒中でフリーデルクラフト反応させ、中間体aを得る。
溶媒が存在する条件下で中間体aを液体臭素と臭素化反応させ、中間体bを生成する。
中間体bを加水分解又は非水酸基光活性基含有化合物と反応させ、目標生成物を得る。
- 中間体bを加水分解により脱ハロゲンする際に、反応系において、中間体bに加えて、有機溶媒及び水で構成されている溶媒系と、無機アルカリと、相転移触媒とをさらに含むことを特徴とする請求項14に記載の製造方法。
- 前記相転移触媒は、テトラブチルアンモニウムブロマイド、テトラプロピルアンモニウムブロマイド、テトラ−n−ブチルアンモニウム、トリエチルベンジルアンモニウムクロライド、硫酸水素テトラブチルアンモニウムからなる群から選ばれることを特徴とする請求項14に記載の製造方法。
- 前記非水酸基光活性基含有化合物はモルホリン又はチオモルホリンであることを特徴とする請求項14に記載の製造方法。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2020507664A (ja) * | 2017-02-17 | 2020-03-12 | 常州強力先端電子材料有限公司Changzhou Tronly Advanced Electronic Materials Co.,Ltd. | フルオレニルアミノケトン類光開始剤、その調製方法及びフルオレニルアミノケトン類光開始剤を含有するuv光硬化性組成物 |
US10976660B2 (en) | 2016-09-13 | 2021-04-13 | Changzhou Tronly Advanced Electronic Materials Co , Ltd. | Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field |
US11054743B2 (en) | 2015-12-15 | 2021-07-06 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorene polyfunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
JP6998490B1 (ja) | 2021-08-30 | 2022-01-18 | サカタインクス株式会社 | 光硬化型インクジェット印刷用インク組成物 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108117616B (zh) * | 2017-11-22 | 2019-08-09 | 惠州市华泓新材料股份有限公司 | 二丁基芴基衍生物与其作为光引发剂的应用 |
JP6999039B2 (ja) * | 2017-12-22 | 2022-02-04 | 常州強力先端電子材料有限公司 | フッ素含有フルオレンオキシムエステル系光開始剤、それを含む光硬化組成物およびその適用 |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH491848A (de) | 1966-07-22 | 1970-06-15 | Sandoz Ag | Verfahren zur Herstellung neuer Arylketone |
DE3008411A1 (de) * | 1980-03-05 | 1981-09-10 | Merck Patent Gmbh, 6100 Darmstadt | Neue aromatisch-aliphatische ketone, ihre verwendung als photoinitiatoren sowie photopolymerisierbare systeme enthaltend solche ketone |
US4533670A (en) | 1983-09-21 | 1985-08-06 | Eli Lilly And Company | Anti-convulsant fluorenylalkylimidazole derivatives, compositions, and method of use |
US4666824A (en) * | 1984-04-23 | 1987-05-19 | Hercules Incorporated | Photopolymer process and composition employing a photooxidizable component capable of forming endoperoxides |
ES2054861T3 (es) | 1987-03-26 | 1994-08-16 | Ciba Geigy Ag | Nuevas alfa-aminoacetofenonas como fotoiniciadores. |
US4950581A (en) | 1987-07-06 | 1990-08-21 | Fuji Photo Film Co., Ltd. | Photopolymerizable composition |
TW328535B (en) | 1993-07-02 | 1998-03-21 | Novartis Ag | Functional photoinitiators and their manufacture |
JP3560980B2 (ja) | 1994-12-30 | 2004-09-02 | ノバルティス アクチエンゲゼルシャフト | ブロック共重合体に基づくポリマー |
TW434456B (en) | 1994-12-30 | 2001-05-16 | Novartis Ag | A compound as functionalized photoinitiator, its production process, its corresponding oligomers or polymers and its application in coating a substrate |
TW353086B (en) | 1994-12-30 | 1999-02-21 | Novartis Ag | Method for multistep coating of a surface |
IT1303775B1 (it) | 1998-11-19 | 2001-02-23 | Lamberti Spa | Fotoiniziatori impiegabili nella fotopolimerizzazione, e relativeformulazioni. |
JP4789329B2 (ja) | 2000-04-03 | 2011-10-12 | Jsr株式会社 | 二層フィルム |
ITVA20030028A1 (it) | 2003-08-07 | 2005-02-08 | Lamberti Spa | Sistemi fotopolimerizzabili trasparenti per la preparazione di rivestimenti ad elevato spessore. |
KR100596364B1 (ko) * | 2004-05-31 | 2006-07-03 | 주식회사 엘지화학 | 감광성 수지 조성물 및 이를 이용하여 제조된 액정표시소자 |
JP2009019142A (ja) | 2007-07-13 | 2009-01-29 | Toyo Ink Mfg Co Ltd | 光硬化型インキ |
JP2009029859A (ja) | 2007-07-25 | 2009-02-12 | Toyo Ink Mfg Co Ltd | 重合性組成物、および重合物の製造方法 |
JP5334477B2 (ja) | 2008-07-16 | 2013-11-06 | 富士フイルム株式会社 | 光硬化性組成物、インク組成物及びそれを用いたインクジェット記録方法 |
CN101724099B (zh) | 2009-12-18 | 2012-09-26 | 深圳市有为化学技术有限公司 | 芳香酮类化合物及含有该化合物的光引发剂 |
CN102267887A (zh) | 2011-07-18 | 2011-12-07 | 连云港升南化学有限公司 | 1-羟基环己基苯基甲酮的合成工艺 |
TWI481965B (zh) | 2011-10-12 | 2015-04-21 | Toyo Ink Sc Holdings Co Ltd | 樹脂組成物、塗膜及觸控面板用絕緣膜 |
WO2013165207A1 (ko) | 2012-05-03 | 2013-11-07 | 한국화학연구원 | 신규한 옥심에스테르 플로렌 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
JP5682094B2 (ja) | 2012-09-28 | 2015-03-11 | ダイトーケミックス株式会社 | フルオレン系化合物、該フルオレン系化合物を含む光重合開始剤、および、該光重合開始剤を含む感光性組成物 |
EP2980059B1 (en) | 2013-03-29 | 2020-01-15 | Tokyo Ohka Kogyo Co., Ltd. | Vinyl-group-containing fluorene compound |
KR101567837B1 (ko) * | 2013-06-11 | 2015-11-11 | 애경화학 주식회사 | 플루오렌 구조를 갖는 신규한 광개시제 및 이를 포함하는 반응성 액정 조성물 및 감광성 조성물 |
KR101939552B1 (ko) | 2013-12-06 | 2019-01-17 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101435652B1 (ko) | 2014-01-17 | 2014-08-28 | 주식회사 삼양사 | 신규한 β-옥심에스테르 플루오렌 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
CN106537254B (zh) | 2014-07-15 | 2021-01-08 | 东京应化工业株式会社 | 感光性组合物及化合物 |
WO2016034963A1 (en) | 2014-09-04 | 2016-03-10 | Basf Se | Polycyclic photoinitiators |
WO2016078603A1 (en) | 2014-11-21 | 2016-05-26 | The Hong Kong University Of Science And Technology | Aie luminogens for bacteria imaging, killing, photodynamic therapy and antibiotics screening, and their methods of manufacturing |
CN104892512B (zh) | 2015-05-21 | 2018-01-05 | 常州强力先端电子材料有限公司 | 一种吡唑啉类增感剂及其制备方法和应用 |
EP3392232B1 (en) | 2015-12-15 | 2021-02-17 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorene multifunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
CN106883114B (zh) | 2015-12-15 | 2019-11-19 | 常州强力先端电子材料有限公司 | 一种芴类多官能度光引发剂及其制备和应用 |
EP3514135B1 (en) | 2016-09-13 | 2021-04-21 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field |
JP7032416B2 (ja) * | 2017-02-17 | 2022-03-08 | 常州強力先端電子材料有限公司 | フルオレニルアミノケトン類光開始剤、その調製方法及びフルオレニルアミノケトン類光開始剤を含有するuv光硬化性組成物 |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11054743B2 (en) | 2015-12-15 | 2021-07-06 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorene polyfunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
US10976660B2 (en) | 2016-09-13 | 2021-04-13 | Changzhou Tronly Advanced Electronic Materials Co , Ltd. | Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field |
JP2020507664A (ja) * | 2017-02-17 | 2020-03-12 | 常州強力先端電子材料有限公司Changzhou Tronly Advanced Electronic Materials Co.,Ltd. | フルオレニルアミノケトン類光開始剤、その調製方法及びフルオレニルアミノケトン類光開始剤を含有するuv光硬化性組成物 |
US11118065B2 (en) | 2017-02-17 | 2021-09-14 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same |
JP7032416B2 (ja) | 2017-02-17 | 2022-03-08 | 常州強力先端電子材料有限公司 | フルオレニルアミノケトン類光開始剤、その調製方法及びフルオレニルアミノケトン類光開始剤を含有するuv光硬化性組成物 |
JP6998490B1 (ja) | 2021-08-30 | 2022-01-18 | サカタインクス株式会社 | 光硬化型インクジェット印刷用インク組成物 |
WO2023032388A1 (ja) * | 2021-08-30 | 2023-03-09 | サカタインクス株式会社 | 光硬化型インクジェット印刷用インク組成物 |
JP2023034087A (ja) * | 2021-08-30 | 2023-03-13 | サカタインクス株式会社 | 光硬化型インクジェット印刷用インク組成物 |
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