TWI641625B - Photocurable composition - Google Patents
Photocurable composition Download PDFInfo
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- TWI641625B TWI641625B TW103105946A TW103105946A TWI641625B TW I641625 B TWI641625 B TW I641625B TW 103105946 A TW103105946 A TW 103105946A TW 103105946 A TW103105946 A TW 103105946A TW I641625 B TWI641625 B TW I641625B
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- Taiwan
- Prior art keywords
- carbon atoms
- group
- compound
- acid
- integer
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- 239000000203 mixture Substances 0.000 title claims abstract description 81
- -1 thiol compound Chemical class 0.000 claims abstract description 121
- 150000001875 compounds Chemical class 0.000 claims abstract description 117
- 239000004593 Epoxy Substances 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims abstract description 31
- 239000003999 initiator Substances 0.000 claims abstract description 18
- 239000003086 colorant Substances 0.000 claims abstract description 14
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 10
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- 238000005886 esterification reaction Methods 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000000049 pigment Substances 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 8
- 230000032050 esterification Effects 0.000 abstract 1
- 229920002120 photoresistant polymer Polymers 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 44
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000975 dye Substances 0.000 description 11
- 239000006229 carbon black Substances 0.000 description 9
- 235000019241 carbon black Nutrition 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 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 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000007519 polyprotic acids Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002484 inorganic compounds Chemical class 0.000 description 7
- 229910010272 inorganic material Inorganic materials 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000011572 manganese Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 6
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 4
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 4
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 239000002184 metal Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JTMBCYAUSCBSEY-UHFFFAOYSA-N 2-methyl-2-sulfanylpropanoic acid Chemical compound CC(C)(S)C(O)=O JTMBCYAUSCBSEY-UHFFFAOYSA-N 0.000 description 3
- MHRDCHHESNJQIS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropanoic acid Chemical compound SCC(C)C(O)=O MHRDCHHESNJQIS-UHFFFAOYSA-N 0.000 description 3
- PMNLUUOXGOOLSP-UHFFFAOYSA-M 2-sulfanylpropanoate Chemical compound CC(S)C([O-])=O PMNLUUOXGOOLSP-UHFFFAOYSA-M 0.000 description 3
- NEAFWRKPYYJETG-UHFFFAOYSA-N 4-sulfanylpentanoic acid Chemical compound CC(S)CCC(O)=O NEAFWRKPYYJETG-UHFFFAOYSA-N 0.000 description 3
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound 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
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- JSYPRLVDJYQMAI-ODZAUARKSA-N (z)-but-2-enedioic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)\C=C/C(O)=O JSYPRLVDJYQMAI-ODZAUARKSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- 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
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
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- 229910001950 potassium oxide Inorganic materials 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 229930006978 terpinene Natural products 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
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- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical class NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 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
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- 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
- G03F7/0005—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
-
- 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
-
- 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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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Epoxy Resins (AREA)
- Optical Filters (AREA)
Abstract
本發明提供一種感度及耐熱性優異、可獲得適當之圖案形狀或微細圖案之高電阻之光硬化性組合物。
本發明之光硬化性組合物含有光聚合性不飽和化合物(A)、多官能硫醇化合物(B)、光聚合起始劑(C)及著色劑(D),且該光聚合性不飽和化合物(A)具有作為如下反應產物之結構,即藉由具有使不飽和一元酸加成於下述通式(I)所表示之環氧化合物而成之結構的環氧加成化合物、與多元酸酐之酯化反應所獲得之反應產物。
(式中,R1、R2、R3、R4、Y、Z、m、p、q、r、s之定義參照說明書)
Description
本發明係關於一種含有具有特定結構之光聚合性不飽和化合物及多官能硫醇化合物的光硬化性組合物。
光硬化性組合物含有顏料、光聚合性不飽和化合物及光聚合起始劑。該光硬化性組合物可藉由照射紫外線或電子束而進行聚合硬化,因此尤其是於使用黑色顏料之情形時,可用於設置於彩色濾光片之R、G、B之著色層間之邊界部分以提高顯示對比度或顯色效果的黑矩陣。
最近,存在如下問題:於黑矩陣之製造步驟中,經過曝光、顯影、後熱處理所獲得之黑色圖案與透明基板之密接性並不充分,從而因反覆進行黑色圖案形成後之剝離步驟,而先前所形成之著色圖案之一部分同時被剝離,圖案產生缺損或曝光硬化部殘留於透明基板上。
下述專利文獻1及2中揭示有一種感光性組合物,其含有作為光聚合起始劑之多官能硫醇及具有乙烯性不飽和鍵之化合物。又,下述專利文獻3中揭示有一種遮光性黑色抗蝕劑組合物,其含有黏合劑樹脂、具有乙烯性不飽和鍵之化合物、光聚合起始劑、黑色顏料、溶劑及硫醇化合物。然而,於專利文獻1及2中,關於本發明之具有特定結構之光聚合性不飽和化合物未作記載亦無暗示,於專利文獻3中,作為上述黏合劑樹脂,關於本案發明之具有特定結構之光聚合性不飽和化合物亦未作記載亦無暗示。又,下述專利文獻4中揭示有一種鹼性
顯影性感光性樹脂組合物,其含有具有特定結構之光聚合性不飽和化合物及光聚合起始劑,但關於併用多官能硫醇一事未作記載亦無暗示。
[專利文獻1]日本專利特開2003-252918號公報
[專利文獻2]日本專利特開2004-325735號公報
[專利文獻3]日本專利特開2004-325734號公報
[專利文獻4]國際公開2008-139924號公報
因此,本發明之目的在於提供一種感度及耐熱性優異、可獲得適當之圖案形狀或微細圖案之高電阻的光硬化性組合物。
本發明者等反覆進行努力研究,結果發現:含有光聚合性不飽和化合物(A)、多官能硫醇化合物(B)、光聚合起始劑(C)及著色劑(D)的光硬化性組合物可達成上述目的,且該光聚合性不飽和化合物(A)具有作為如下反應產物之結構,即藉由具有使不飽和一元酸加成於下述通式(I)所表示之環氧化合物而成之結構的環氧加成化合物、與多元酸酐之酯化反應所獲得之反應產物;又發現上述光硬化性組合物適於彩色濾光片,從而完成本發明。
[化1]
(式中,R1、R2、R3及R4各自獨立表示氫原子、碳原子數1~5之烷基、碳原子數1~8之烷氧基、碳原子數2~5之烯基或鹵素原子,Y及Z各自獨立表示碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳烷基、碳原子數2~20之雜環基、或鹵素原子,上述烷基及芳烷基中之伸烷基部分亦可被不飽和鍵、-O-或-S-中斷,Z亦可為由鄰接之Z彼此形成環,m表示0~10之整數,p表示0~4之整數,q表示0~8之整數,r表示0~4之整數,s表示0~4之整數,r與s之數之合計為2~4之整數)
又,本發明提供一種使用上述光硬化性組合物之彩色濾光片。
根據本發明,含有具有特定結構之光聚合性不飽和化合物的光硬化性組合物為感度及耐熱性優異者。又,其硬化物適於顯示器件用彩色濾光片及液晶顯示面板以及有機EL(Electroluminescence,電致發光)顯示面板。
以下,基於較佳之實施形態說明本發明之光硬化性組合物。
本發明之光硬化性組合物含有光聚合性不飽和化合物(A)、多官能硫醇化合物(B)、光聚合起始劑(C)及著色劑(D),且該光聚合性不飽和化合物(A)具有作為如下反應產物之結構,即藉由具有使不飽和一
元酸加成於上述通式(I)所表示之環氧化合物而成之結構的環氧加成化合物、與多元酸酐之酯化反應所獲得之反應產物。以下,依序說明各成分。
本發明之光硬化性組合物所使用之光聚合性不飽和化合物(A)具有作為如下反應產物之結構,即藉由具有使不飽和一元酸加成於上述通式(I)所表示之環氧化合物而成之結構的環氧加成化合物、與多元酸酐之酯化反應所獲得之反應產物。
於上述通式(I)中,作為R1、R2、R3及R4所表示之碳原子數1~5之烷基,可列舉:甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基、戊基、異戊基、第三戊基等,作為R1、R2、R3及R4所表示之碳原子數1~8之烷氧基,可列舉:甲氧基、乙氧基、異丙氧基、丙氧基、丁氧基、戊氧基、異戊氧基、己氧基、庚氧基、辛氧基、2-乙基己氧基等,作為R1、R2、R3及R4所表示之碳原子數2~5之烯基,可列舉:乙烯基、烯丙基、丁烯基、丙烯基等,作為R1、R2、R3及R4所表示之鹵素原子,可列舉:氟原子、氯原子、溴原子、碘原子。
於上述通式(I)中,作為Y及Z所表示之碳原子數1~20之烷基,除上述R1、R2、R3及R4中所例示者以外,亦可列舉:己基、庚基、異庚基、第三庚基、正辛基、異辛基、第三辛基、2-乙基己基、正壬基、正癸基、三氟甲基、二氟甲基、單氟甲基、五氟乙基、四氟乙基、三氟乙基、二氟乙基、七氟丙基、六氟丙基、五氟丙基、四氟丙基、三氟丙基、全氟丁基、環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基等,作為Y及Z所表示之碳原子數6~30之芳基,可列舉:苯基、萘
基、蒽-1-基、菲-1-基、鄰甲苯基、間甲苯基、對甲苯基、4-乙烯基苯基、3-異丙基苯基、4-異丙基苯基、4-丁基苯基、4-異丁基苯基、4-第三丁基苯基、4-己基苯基、4-環己基苯基、4-辛基苯基、4-(2-乙基己基)苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2,4-二-第三丁基苯基、2,5-二-第三丁基苯基、2,6-二-第三丁基苯基、2,4-二-第三戊基苯基、2,5-二-第三戊基苯基、環己基苯基、聯苯基、2,4,5-三甲基苯基、4-氯苯基、3,4-二氯苯基、4-三氯苯基、4-三氟苯基、全氟苯基等,作為Y及Z所表示之碳原子數7~30之芳烷基,可列舉:苄基、苯乙基、2-苯丙基、二苯甲基、三苯甲基、苯乙烯基、苯烯丙基、4-氯苯甲基等,作為Y及Z所表示之雜環基,可列舉:吡咯基、吡啶基、嘧啶基、嗒基、哌基、哌啶基、吡喃基、吡唑基、三基、吡咯啶基、喹啉基、異喹啉基、咪唑基、苯并咪唑基、三唑基、呋喃基(furyl)、呋喃基(furanyl)、苯并呋喃基、噻吩基(thienyl)、噻吩基(thiophenyl)、苯并噻吩基、噻二唑基、噻唑基、苯并噻唑基、唑基、苯并唑基、異噻唑基、異唑基、吲哚基、咯啶基、啉基、硫代啉基、2-吡咯啶酮-1-基、2-哌啶酮-1-基、2,4-二氧基咪唑啶-3-基、2,4-二氧基唑啶-3-基等。
上述通式(I)所表示之環氧化合物之中,就進一步提高本發明之效果之觀點而言,較佳為r與s之合計為2或3之整數之化合物,更佳為r與s之合計為2之化合物,尤佳為r為0且s為2之化合物。
作為作用於上述環氧化合物之環氧基之上述不飽和一元酸,可列舉:丙烯酸、甲基丙烯酸、丁烯酸、桂皮酸、山梨酸、甲基丙烯酸羥乙酯-順丁烯二酸酯、丙烯酸羥乙酯-順丁烯二酸酯、甲基丙烯酸羥
丙酯-順丁烯二酸酯、丙烯酸羥丙酯-順丁烯二酸酯、二環戊二烯-順丁烯二酸酯等。
又,作為於上述不飽和一元酸加成後進行酯化反應之上述多元酸酐,可列舉:聯苯四羧酸二酐、四氫鄰苯二甲酸酐、琥珀酸酐、順丁烯二酸酐、偏苯三甲酸酐、均苯四甲酸酐、2,2'-3,3'-二苯甲酮四羧酸酐、乙二醇雙脫水偏苯三酸酯、甘油三脫水偏苯三酸酯、六氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、耐地酸酐、甲基耐地酸酐、三烷基四氫鄰苯二甲酸酐、六氫鄰苯二甲酸酐、5-(2,5-二側氧四氫呋喃基)-3-甲基-3-環己烯-1,2-二羧酸酐、三烷基四氫鄰苯二甲酸酐-順丁烯二酸酐加成物、十二烯基琥珀酸酐、甲基雙環庚烯二甲酸酐等。
較佳為將上述環氧化合物、上述不飽和一元酸及上述多元酸酐之反應莫耳比設為如下所述。
即,較佳為使之成為如下比率:關於具有使上述不飽和一元酸之羧基以0.1~1.0個加成於上述環氧化合物之1個環氧基而成之結構的環氧加成物,相對於該環氧加成物之1個羥基,上述多元酸酐之酸酐結構為0.1~1.0個。
上述環氧化合物、上述不飽和一元酸及上述多元酸酐之反應可依據常法而進行。
就進一步提高本發明之效果之觀點而言,上述光聚合性不飽和化合物(A)之數量平均分子量Mn較佳為300~5000,更佳為500~2500。又,上述光聚合性不飽和化合物(A)之固形物成分之酸值較佳為20~100mgKOH/g,更佳為40~100mgKOH/g。
於本發明之光硬化性組合物中,上述光聚合性不飽和化合物(A)之含量於本發明之光硬化性組合物之固形物成分中,較佳為5~80質量%,尤佳為10~40質量%。若光聚合性不飽和化合物之含量小於5質量%,則存在發生硬化不良之情況,若光聚合性不飽和化合物之含量
大於80質量%,則存在無法獲得充分之遮光性之情況。
作為本發明之光硬化性組合物所使用之多官能硫醇化合物(B),可使用先前公知者,就耐熱性方面而言,尤其下述通式(II)所表示者較佳。
(式中,Q為碳原子數1~10之伸烷基,n表示2~6之整數,X1表示具有與n相同之價數之碳原子數1~20之飽和烴基)
於上述通式(II)中,作為X1所表示之碳原子數1~20之飽和烴基,可列舉於上述通式(I)之說明中作為上述碳原子數1~20之烷基所例示者,作為Q所表示之碳原子數1~10之伸烷基,可列舉:亞甲基、伸乙基、伸丙基、甲基伸乙基、伸丁基、1-甲基伸丙基、2-甲基伸丙基、1,2-二甲基伸丙基、1,3-甲基伸丙基、1-甲基伸丁基、2-甲基伸丁基、3-甲基伸丁基、2,4-二甲基伸丁基、1,3-二甲基伸丁基、伸戊基、伸己基、伸庚基、伸辛基、乙烷-1,1-二基、丙烷-2,2-二基等。
於上述通式(II)中,就耐熱性方面而言,較佳為n為2或4。又,就感度方面而言,較佳為n為3以上,尤佳為4以上。
作為上述通式(II)所表示之化合物,例如可列舉:1,4-雙(3-巰基丁醯氧基)丁烷、乙二醇雙(3-巰基丁酸酯)、二乙二醇雙(3-巰基丁酸
酯)、丁二醇雙(3-巰基丁酸酯)、辛二醇雙(3-巰基丁酸酯)、壬二醇雙(3-巰基丁酸酯)、季戊四醇四(3-巰基丁酸酯)、二季戊四醇六(3-巰基丁酸酯)、乙二醇雙(2-巰基丙酸酯)、二乙二醇雙(2-巰基丙酸酯)、丁二醇雙(2-巰基丙酸酯)、辛二醇雙(2-巰基丙酸酯)、壬二醇雙(2-巰基丙酸酯)、季戊四醇四(2-巰基丙酸酯)、二季戊四醇六(2-巰基丙酸酯)、乙二醇雙(3-巰基異丁酸酯)、二乙二醇雙(3-巰基異丁酸酯)、丁二醇雙(3-巰基異丁酸酯)、辛二醇雙(3-巰基異丁酸酯)、壬二醇雙(3-巰基異丁酸酯)、二季戊四醇六(3-巰基異丁酸酯)、乙二醇雙(2-巰基異丁酸酯)、二乙二醇雙(2-巰基異丁酸酯)、丁二醇雙(2-巰基異丁酸酯)、辛二醇雙(2-巰基異丁酸酯)、壬二醇雙(2-巰基異丁酸酯)、季戊四醇四(2-巰基異丁酸酯)、二季戊四醇六(2-巰基異丁酸酯)、乙二醇雙(4-巰基戊酸酯)、二乙二醇雙(4-巰基戊酸酯)、丁二醇雙(4-巰基戊酸酯)、辛二醇雙(4-巰基戊酸酯)、壬二醇雙(4-巰基戊酸酯)、季戊四醇四(4-巰基戊酸酯)、二季戊四醇六(4-巰基戊酸酯)、乙二醇雙(3-巰基戊酸酯)、二乙二醇雙(3-巰基戊酸酯)、丁二醇雙(3-巰基戊酸酯)、辛二醇雙(3-巰基戊酸酯)、壬二醇雙(3-巰基戊酸酯)、季戊四醇四(3-巰基戊酸酯)、二季戊四醇六(3-巰基戊酸酯)等。
作為多官能硫醇化合物(B),除上述通式(II)所表示之化合物以外,亦可使用2-(N,N-二丁胺基)-4,6-二巰基-對稱三、2,5-己二硫醇、2,9-癸二硫醇、1,4-雙(1-巰基乙基)苯等。
於本發明之光硬化性組合物中,上述多官能硫醇化合物(B)之含量於本發明之光硬化性組合物中,較佳為0.05~5質量%,尤佳為0.5~5質量%。若上述多官能硫醇化合物之含量小於0.05質量%,則存在由曝光引起之硬化變得不充分之情況,若大於5質量%,則亦存在光聚合性不飽和化合物與多官能硫醇化合物變得易發生反應而使保存穩定性較差而發生凝膠化的情況。
作為本發明之光硬化性組合物所使用之光聚合起始劑(C),可使用先前已知之化合物,例如可列舉:二苯甲酮、苯基聯苯基酮、1-羥基-1-苯甲醯環己烷、4-苯甲醯-4'-甲基二苯硫醚、安息香丁醚、2-羥基-2-苯甲醯丙烷、2-羥基-2-(4'-異丙基)苯甲醯丙烷、4-丁基苯甲醯三氯甲烷、4-苯氧基苯甲醯二氯甲烷、苯甲醯甲酸甲酯、安息香、2-啉基-2-(4'-甲基巰基)苯甲醯丙烷、2,2-二甲氧基-1,2-二苯基乙烷-1-酮、1-苄基-1-二甲胺基-1-(4'-啉基苯甲醯)丙烷等苯烷基酮系化合物;1,2-辛二酮,1-[4-(苯硫基)-,2-(鄰苯甲醯肟)]、乙酮,1-[9-乙基-6-(2-甲基苯甲醯)-9H-咔唑-3-基]-,1-(鄰乙醯肟)等肟酯化合物;9-氧硫、1-氯-4-丙氧基9-氧硫、異丙基9-氧硫、二乙基9-氧硫等9-氧硫化合物;乙基蒽醌等蒽醌化合物;2,2-雙(2-氯苯基)-4,5,4',5'-四苯基-1-2'-聯咪唑等聯咪唑化合物;2-甲基-4,6-雙(三氯甲基)-對稱三、2-苯基-4,6-雙(三氯甲基)-對稱三、2-萘基-4,6-雙(三氯甲基)-對稱三等三化合物;4,4-偶氮二異丁腈等偶氮化合物;過氧化苯甲醯等過氧化物;1,7-雙(9'-吖啶基)庚烷、9-正丁基-3,6-雙(2'-啉基異丁醯基)咔唑、三苯基膦、樟腦醌等,作為市售品,可列舉:N-1414、N-1717、N-1919、PZ-808、NCI-831、NCI-930(ADEKA(股)公司製造),IRGACURE184、IRGACURE369、IRGACURE651、IRGACURE907、IRGACURE OXE 01、IRGACURE OXE 02(BASF(股)公司製造)等。
作為本發明之光硬化性組合物所使用之光聚合起始劑,就感度及耐熱性方面而言,尤其下述通式(III)所表示之化合物較佳。
[化3]
(式中,R6及R7各自獨立表示氫原子、氰基、碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳烷基或碳原子數2~20之雜環基,R8及R9各自獨立表示氫原子、鹵素原子、硝基、氰基、羥基、羧基、R10、OR11、SR12、NR13R14、COR15、SOR16、SO2R17或CONR18R19,R8及R9亦可相互鍵結而形成環,R10、R11、R12、R13、R14、R15、R16、R17、R18及R19各自獨立表示碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳烷基或碳原子數2~20之雜環基,X2表示氧原子、硫原子、硒原子、CR20R21、CO、NR22或PR23,X3表示單鍵或CO,R20、R21、R22及R23各自獨立表示氫原子、碳原子數1~20之烷基、碳原子數6~30之芳基或碳原子數7~30之芳烷基,上述烷基或芳烷基中之亞甲基可經鹵素原子、硝基、氰基、羥基、羧基或雜環基取代,亦可被-O-中斷,R20、R21、R22及R23亦可各自獨立地與鄰接之任一苯環一起形成環,a表示0~4之整數,b表示0~5之整數)。
於本發明之光硬化性組合物中,上述光聚合起始劑之含量於本發明之光硬化性組合物之固形物成分中,較佳為0.1~30質量%,尤佳
為0.5~10質量%。若上述光聚合起始劑之含量小於0.1質量%,則存在由曝光引起之硬化變得不充分之情況,若大於30質量%,則存在樹脂組合物中析出起始劑之情況。
作為本發明之光硬化性組合物所使用之著色劑(D),可使用無機色材或有機色材,該等可單獨使用或混合2種以上使用。
作為上述無機色材或有機色材,例如可使用:亞硝基化合物、硝基化合物、偶氮化合物、二偶氮化合物、化合物、喹啉化合物、蒽醌化合物、香豆素化合物、酞菁化合物、異吲哚啉酮化合物、異吲哚啉化合物、喹吖啶酮化合物、蒽締蒽酮化合物、哌瑞酮化合物、苝化合物、吡咯并吡咯二酮化合物、硫靛藍化合物、二化合物、三苯甲烷化合物、喹酞酮化合物、萘四羧酸;偶氮染料、花青染料之金屬錯合物;色澱顏料;由爐法、導槽法、熱法所獲得之碳黑、或乙炔黑、科琴黑或燈黑等碳黑;利用環氧樹脂調整、被覆上述碳黑而成者、預先於溶劑中利用樹脂對上述碳黑進行分散處理而使之吸附20~200mg/g之樹脂而成者、對上述碳黑進行酸性或鹼性表面處理而成者、平均粒徑為8nm以上且DBP(Dibutyl phthalate,鄰苯二甲酸二丁酯)吸油量為90ml/100g以下者、根據950℃下之揮發分中之CO、CO2算出之氧總量為碳黑之每100m2表面積為9mg以上者;石墨、石墨化碳黑、活性碳、碳纖維、碳奈米管、螺旋碳纖維、碳奈米角、碳氣凝膠、富勒烯;苯胺黑、顏料黑7、鈦黑;合成鐵黑;疏水性樹脂、氧化鉻綠、米洛麗藍、鈷綠、鈷藍、錳系、亞鐵氰化物、磷酸鹽群青、鐵藍、群青、天藍、濃綠、翡翠綠、硫酸鉛、黃丹、鋅黃、鐵丹(紅色氧化鐵(III))、鎘紅、棕土等無機顏料或有機顏料。
作為上述無機色材或有機色材,亦可使用市售之顏料,例如可列舉:顏料紅1、2、3、9、10、14、17、22、23、31、38、41、48、
49、88、90、97、112、119、122、123、144、149、166、168、169、170、171、177、179、180、184、185、192、200、202、209、215、216、217、220、223、224、226、227、228、240、254;顏料橙13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65、71;顏料黃1、3、12、13、14、16、17、20、24、55、60、73、81、83、86、93、95、97、98、100、109、110、113、114、117、120、125、126、127、129、137、138、139、147、148、150、151、152、153、154、166、168、175、180、185;顏料綠7、10、36;顏料藍15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62、64;顏料紫1、19、23、27、29、30、32、37、40、50等。
作為上述無機色材或有機色材,亦可使用公知之染料。作為公知之染料,例如可列舉:偶氮染料、蒽醌染料、靛類染料、三芳基甲烷染料、染料、茜素染料、吖啶染料、茋染料、噻唑染料、萘酚染料、喹啉染料、硝基染料、吲達胺染料、染料、酞菁染料、花青染料等染料等。
於本發明之光硬化性組合物中,上述著色劑(D)之含量相對於包含上述光聚合性不飽和化合物在內之具有乙烯性不飽和鍵之聚合性化合物整體100質量份,較佳為0~350質量份,更佳為0~300質量份,進而較佳為0~250質量份。若超過350質量份,則著色劑變得易凝集而保存穩定性變差。
本發明之光硬化性組合物中進而可使用光聚合性不飽和化合物(A)以外之具有乙烯性不飽和鍵之聚合性化合物。作為該具有乙烯性不飽和鍵之聚合性化合物,並無特別限定,可使用先前用於感光性組合物中者,例如可列舉:乙烯、丙烯、丁烯、異丁烯、氯乙烯、偏二氯乙烯、偏二氟乙烯、四氟乙烯等不飽和脂肪族烴;(甲基)丙烯酸、
α-氯丙烯酸、伊康酸、順丁烯二酸、檸康酸、反丁烯二酸、雙環庚烯二甲酸、丁烯酸、異丁烯酸、乙烯基乙酸、烯丙基乙酸、桂皮酸、山梨酸、中康酸、琥珀酸單[2-(甲基)丙烯醯氧基乙基]酯、鄰苯二甲酸單[2-(甲基)丙烯醯氧基乙基]酯、ω-羧基聚己內酯單(甲基)丙烯酸酯等於兩末端具有羧基與羥基之聚合物之單(甲基)丙烯酸酯;(甲基)丙烯酸羥乙酯-順丁烯二酸酯、(甲基)丙烯酸羥丙酯-順丁烯二酸酯、二環戊二烯-順丁烯二酸酯或具有1個羧基與2個以上(甲基)丙烯醯基之多官能(甲基)丙烯酸酯等不飽和一元酸;(甲基)丙烯酸-2-羥基乙酯、(甲基)丙烯酸-2-羥基丙酯、(甲基)丙烯酸縮水甘油酯、下述化合物No.A1~No.A4、(甲基)丙烯酸甲酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸-第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸甲氧基乙酯、(甲基)丙烯酸二甲胺基甲酯、(甲基)丙烯酸二甲胺基乙酯、(甲基)丙烯酸胺基丙酯、(甲基)丙烯酸二甲胺基丙酯、(甲基)丙烯酸乙氧基乙酯、(甲基)丙烯酸聚(乙氧基)乙酯、(甲基)丙烯酸丁氧基乙氧基乙酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸四氫呋喃酯、(甲基)丙烯酸乙烯酯、(甲基)丙烯酸烯丙酯、(甲基)丙烯酸苄酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、三羥甲基乙烷三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、三環癸烷二羥甲基二(甲基)丙烯酸酯、異氰尿酸三[(甲基)丙烯醯基乙基]酯、聚酯(甲基)丙烯酸酯低聚物等不飽和一元酸及多元醇或多酚之酯;(甲
基)丙烯酸鋅、(甲基)丙烯酸鎂等不飽和多元酸之金屬鹽;順丁烯二酸酐、伊康酸酐、檸康酸酐、甲基四氫鄰苯二甲酸酐、四氫鄰苯二甲酸酐、三烷基四氫鄰苯二甲酸酐、5-(2,5-二側氧四氫呋喃基)-3-甲基-3-環己烯-1,2-二羧酸酐、三烷基四氫鄰苯二甲酸酐-順丁烯二酸酐加成物、十二烯基琥珀酸酐、甲基雙環庚烯二甲酸酐等不飽和多元酸之酸酐;(甲基)丙烯醯胺、亞甲基雙-(甲基)丙烯醯胺、二伸乙基三胺三(甲基)丙烯醯胺、苯二甲基雙(甲基)丙烯醯胺、α-氯丙烯醯胺、N-2-羥基乙基(甲基)丙烯醯胺等不飽和一元酸及多元胺之醯胺;丙烯醛等不飽和醛;(甲基)丙烯腈、α-氯丙烯腈、二氰亞乙烯、氰化丙烯等不飽和腈;苯乙烯、4-甲基苯乙烯、4-乙基苯乙烯、4-甲氧基苯乙烯、4-羥基苯乙烯、4-氯苯乙烯、二乙烯苯、乙烯基甲苯、乙烯基苯甲酸、乙烯基苯酚、乙烯基磺酸、4-乙烯基苯磺酸、乙烯基苄基甲醚、乙烯基苄基縮水甘油醚等不飽和芳香族化合物;甲基乙烯基酮等不飽和酮;乙烯胺、烯丙胺、N-乙烯基吡咯啶酮、乙烯基哌啶等不飽和胺化合物;烯丙醇、巴豆醇等乙烯醇;乙烯基甲醚、乙烯基乙醚、正丁基乙烯醚、異丁基乙烯醚、烯丙基縮水甘油醚等乙烯醚;順丁烯二醯亞胺、N-苯基順丁烯二醯亞胺、N-環己基順丁烯二醯亞胺等不飽和醯亞胺類;茚、1-甲基茚等茚類;1,3-丁二烯、異戊二烯、氯丁二烯等脂肪族共軛二烯類;聚苯乙烯、聚(甲基)丙烯酸甲酯、聚(甲基)丙烯酸正丁酯、聚矽氧烷等於聚合物分子鏈之末端具有單(甲基)丙烯醯基之巨單體類;氯乙烯、偏二氯乙烯、丁二酸二乙烯酯、鄰苯二甲酸二烯丙酯、磷酸三烯丙酯、異氰尿酸三烯丙酯、乙烯基硫醚、乙烯基咪唑、乙烯基唑啉、乙烯基咔唑、乙烯基吡咯啶酮、乙烯基吡啶、含羥基之乙烯基單體及聚異氰酸酯化合物之乙烯基胺基甲酸酯化合物、含羥基之乙烯基單體及聚環氧化合物之乙烯基環氧化合物。
[化4]
又,作為上述具有乙烯性不飽和鍵之聚合性化合物,亦可使用丙烯酸酯之共聚物、或者苯酚及/或甲酚酚醛清漆環氧樹脂、具有多官能環氧基之聚苯甲烷型環氧樹脂。
於上述具有乙烯性不飽和鍵之聚合性化合物中,使用具有酸值之化合物之情形時,可對本發明之光硬化性組合物賦予鹼性顯影性。
於使用上述具有酸值之化合物之情形時,較佳為使其使用量成為上述具有乙烯性不飽和鍵之聚合性化合物整體之50~99質量%。
又,上述具有酸值之化合物亦可於進而藉由使單官能或多官能環氧化合物反應而調整酸值後使用。藉由對上述具有酸值之化合物之酸值進行調整,可改良感光性樹脂之鹼性顯影性。上述具有酸值之化合物(即賦予鹼性顯影性之具有乙烯性不飽和鍵之聚合性化合物)較佳為固形物成分之酸值為5~120mgKOH/g之範圍,單官能或多官能環氧化合物之使用量較佳為以滿足上述酸值之方式進行選擇。
作為上述單官能環氧化合物,可列舉:甲基丙烯酸縮水甘油酯、甲基縮水甘油醚、乙基縮水甘油醚、丙基縮水甘油醚、異丙基縮水甘油醚、丁基縮水甘油醚、異丁基縮水甘油醚、第三丁基縮水甘油醚、戊基縮水甘油醚、己基縮水甘油醚、庚基縮水甘油醚、辛基縮水甘油醚、壬基縮水甘油醚、癸基縮水甘油醚、十一烷基縮水甘油醚、十二烷基縮水甘油醚、十三烷基縮水甘油醚、十四烷基縮水甘油醚、十五烷基縮水甘油醚、十六烷基縮水甘油醚、2-乙基己基縮水甘油醚、烯丙基縮水甘油醚、炔丙基縮水甘油醚、對甲氧基乙基縮水甘油醚、苯基縮水甘油醚、對甲氧基縮水甘油醚、對丁基苯酚縮水甘油醚、甲苯基縮水甘油醚、2-甲基甲苯基縮水甘油醚、4-壬基苯基縮水甘油醚、苄基縮水甘油醚、對異丙苯基苯基縮水甘油醚、三苯甲基縮水甘油醚、甲基丙烯酸2,3-環氧丙酯、環氧化大豆油、環氧化亞麻子油、丁酸縮水甘油酯、一氧化乙烯基環己烷、1,2-環氧-4-乙烯基環己烷、氧化苯乙烯、氧化蒎烯、氧化甲基苯乙烯、氧化環己烯、氧化丙烯、上述化合物No.A2、No.A3等。
作為上述多官能環氧化合物,若使用選自由雙酚型環氧化合物及縮水甘油醚類所組成之群中之一種以上化合物,則可獲得特性更良好之光硬化性組合物,因此較佳。
作為上述雙酚型環氧化合物,可使用上述通式(I)所表示之環氧化合物,除此以外,亦可使用例如氫化雙酚型環氧化合物等雙酚型環氧化合物。
又,作為上述縮水甘油醚類,可使用:乙二醇二縮水甘油醚、丙二醇二縮水甘油醚、1,4-丁二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚、1,8-辛二醇二縮水甘油醚、1,10-癸二醇二縮水甘油醚、2,2-二甲基-1,3-丙二醇二縮水甘油醚、二乙二醇二縮水甘油醚、三乙二醇二縮水甘油醚、四乙二醇二縮水甘油醚、六乙二醇二縮水甘油醚、1,4-環己烷二甲醇二縮水甘油醚、1,1,1-三(縮水甘油氧基甲基)丙烷、1,1,1-三(縮水甘油氧基甲基)乙烷、1,1,1-三(縮水甘油氧基甲基)甲烷、1,1,1,1-四(縮水甘油氧基甲基)甲烷等。
除此以外,亦可使用:苯酚酚醛清漆型環氧化合物、聯苯酚醛清漆型環氧化合物、甲酚酚醛清漆型環氧化合物、雙酚A酚醛清漆型環氧化合物、二環戊二烯酚醛清漆型環氧化合物等酚醛清漆型環氧化合物;3,4-環氧-6-甲基環己基甲基-3,4-環氧-6-甲基環己烷羧酸酯、3,4-環氧環己基甲基-3,4-環氧環己烷羧酸酯、1-環氧乙基-3,4-環氧環己烷等脂環式環氧化合物;鄰苯二甲酸二縮水甘油酯、四氫鄰苯二甲酸二縮水甘油酯、二聚酸縮水甘油酯等縮水甘油酯類;四縮水甘油基二胺基二苯甲烷、三縮水甘油基對胺基苯酚、N,N-二縮水甘油基苯胺等縮水甘油胺類;1,3-二縮水甘油基-5,5-二甲基乙內醯脲、異氰尿酸三縮水甘油酯等雜環式環氧化合物;二氧化二環戊二烯等二氧化物;萘型環氧化合物;三苯甲烷型環氧化合物;二環戊二烯型環氧化合物等。
又,本發明之光硬化性組合物亦可含有不具有乙烯性不飽和鍵但會賦予鹼性顯影性之化合物,作為此種化合物,只要為藉由具有酸值而可溶於鹼性水溶液之化合物,則並無特別限定,作為代表性者,
可列舉鹼可溶性酚醛樹脂(以下簡稱為「酚醛樹脂」)。酚醛樹脂係使酚類與醛類於酸觸媒之存在下進行聚縮合而獲得。
作為上述酚類,例如使用:苯酚、鄰甲酚、間甲酚、對甲酚、鄰乙基苯酚、間乙基苯酚、對乙基苯酚、鄰丁基苯酚、間丁基苯酚、對丁基苯酚、2,3-二甲苯酚、2,4-二甲苯酚、2,5-二甲苯酚、3,4-二甲苯酚、3,5-二甲苯酚、2,3,5-三甲基苯酚、對苯基苯酚、氫醌、兒茶酚、間苯二酚、2-甲基間苯二酚、鄰苯三酚、α-萘酚、雙酚A、苯甲酸二羥酯、沒食子酸酯等,較佳為該等酚類中之苯酚、鄰甲酚、間甲酚、對甲酚、2,5-二甲苯酚、3,5-二甲苯酚、2,3,5-三甲基苯酚、間苯二酚、2-甲基間苯二酚及雙酚A。該等酚類可單獨使用或混合2種以上使用。
作為上述醛類,例如使用:甲醛、多聚甲醛、乙醛、丙醛、苯甲醛、苯乙醛、α-苯丙醛、β-苯丙醛、鄰羥基苯甲醛、間羥基苯甲醛、對羥基苯甲醛、鄰氯苯甲醛、間氯苯甲醛、對氯苯甲醛、鄰硝基苯甲醛、間硝基苯甲醛、對硝基苯甲醛、鄰甲基苯甲醛、間甲基苯甲醛、對甲基苯甲醛、對乙基苯甲醛、對正丁基苯甲醛等,較佳為該等化合物中之甲醛、乙醛及苯甲醛。該等醛類可單獨使用或混合2種以上使用。醛類係以相對於酚類1莫耳較佳為0.7~3莫耳、尤佳為0.7~2莫耳之比率使用。
作為上述酸觸媒,例如使用:鹽酸、硝酸、硫酸等無機酸,或甲酸、草酸、乙酸等有機酸。該等酸觸媒之使用量較佳為相對於酚類1莫耳而為1×10-4~5×10-1莫耳。於縮合反應中,通常使用水作為反應介質,但縮合反應中所使用之酚類不溶於醛類之水溶液而自反應初期即形成不均勻之體系,於該情形時,亦可使用親水性溶劑作為反應介質。作為該等親水性溶劑,例如可列舉:甲醇、乙醇、丙醇、丁醇等醇類,或四氫呋喃、二烷等環狀醚類。該等反應介質之使用量通常
相對於反應原料100質量份為20~1000質量份。縮合反應之反應溫度可根據反應原料之反應性而適當調整,通常為10~200℃,較佳為70~150℃。縮合反應結束後,為了將存在於體系內之未反應原料、酸觸媒及反應介質去除,一般而言使內溫上升至130~230℃,並於減壓下蒸餾去除揮發分,繼而使已熔融之酚醛樹脂流延於鋼製帶等上而進行回收。
又,亦可藉由如下方式進行回收:於縮合反應結束後,使反應混合物溶解於上述親水性溶劑中,添加於水、正己烷、正庚烷等沈澱劑中,藉此使酚醛樹脂析出,而分離析出物並進行加熱乾燥。
作為上述酚醛樹脂以外之例,可列舉:聚羥基苯乙烯或其衍生物、苯乙烯-順丁烯二酸酐共聚物、聚羥基苯甲酸乙烯酯等。
本發明之光硬化性組合物中進而可添加溶劑。作為該溶劑,通常為視需要可使上述各成分(本發明之光聚合性不飽和化合物(A)、多官能硫醇化合物(B)、光聚合起始劑(C)、著色劑(D)等)溶解或分散之溶劑,例如可列舉:甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、甲基異丁基酮、環己酮、2-庚酮等酮類;乙醚、二烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二丙二醇二甲醚等醚系溶劑;乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸正丁酯、乙酸環己酯、乳酸乙酯、琥珀酸二甲酯、TEXANOL等酯系溶劑;乙二醇單甲醚、乙二醇單乙醚等溶纖素系溶劑;甲醇、乙醇、異或正丙醇、異或正丁醇、戊醇等醇系溶劑;乙二醇單甲基乙酸酯、乙二醇單乙基乙酸酯、丙二醇-1-單甲醚-2-乙酸酯(PGMEA)、二丙二醇單甲醚乙酸酯、乙酸3-甲氧基丁酯、丙酸乙氧基乙酯等醚酯系溶劑;苯、甲苯、二甲苯等BTX系溶劑;己烷、庚烷、辛烷、環己烷等脂肪族烴系溶劑;松節油、D-檸檬烯、蒎烯等萜烯系烴油;礦油精、Swazol#310(Cosmo Matsuyama Oil(股))、Solvesso#100(Exxon
Chemical(股))等石蠟系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷、1,2-二氯乙烷等鹵化脂肪族烴系溶劑;氯苯等鹵化芳香族烴系溶劑;卡必醇系溶劑、苯胺、三乙基胺、吡啶、乙酸、乙腈、二硫化碳、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、二甲基亞碸、水等。該等溶劑可使用1種或以2種以上之混合溶劑之形式使用。該等之中,較佳為酮類、醚酯系溶劑等,尤佳為丙二醇-1-單甲醚-2-乙酸酯(PGMEA)、環己酮等,其原因在於:於光硬化性組合物中抗蝕劑與光聚合起始劑之相溶性較佳。
於本發明之光硬化性組合物中,上述溶劑之使用量較佳為溶劑以外之組合物之濃度成為5~30質量%,於小於5質量%之情形時,難以使膜厚變厚,無法充分吸收所期望之波長之光,因此欠佳,於超過30質量%之情形時,因組合物之析出而導致組合物之保存性下降或黏度提高,故而操作性下降,因此欠佳。
進而可使本發明之光硬化性組合物中含有無機化合物。作為該無機化合物,例如可列舉:氧化鎳、氧化鐵、氧化銥、氧化鈦、氧化鋅、氧化鎂、氧化鈣、氧化鉀、二氧化矽、氧化鋁等金屬氧化物;層狀黏土礦物、米洛麗藍、碳酸鈣、碳酸鎂、鈷系、錳系、玻璃粉末、雲母、滑石、高嶺土、亞鐵氰化物、各種金屬硫酸鹽、硫化物、硒化物、矽酸鋁、矽酸鈣、氫氧化鋁、鉑、金、銀、銅等,該等之中,較佳為氧化鈦、二氧化矽、層狀黏土礦物、銀等。於本發明之光硬化性組合物中,無機化合物之含量相對於上述光聚合性不飽和化合物100質量份,較佳為0.1~50質量份,更佳為0.5~20質量份,該等無機化合物可使用1種或2種以上。
藉由使本發明之光硬化性組合物含有無機化合物,而可用作感光性漿料組合物。該感光性漿料組合物係用於形成電漿顯示面板之間隔壁圖案、介電體圖案、電極圖案及黑矩陣圖案等焙燒物圖案。
又,該等無機化合物亦可較佳地用作例如填充劑、抗反射劑、導電劑、穩定劑、阻燃劑、機械強度提高劑、特殊波長吸收劑、撥墨劑等。
於在本發明之光硬化性組合物中使用顏料或無機化合物之情形時,可添加分散劑。作為該分散劑,只要為可使色材或無機化合物分散、穩定化者,則可為任意者,可使用市售之分散劑,例如BYK-Chemie公司製造之BYK系列等,較佳地使用如下者:包含具有鹼性官能基之聚酯、聚醚、聚胺基甲酸酯的高分子分散劑,鹼性官能基具有氮原子,具有氮原子之官能基為胺及/或其四級鹽,胺值為1~100mgKOH/g。
又,本發明之光硬化性組合物中,視需要可添加如下慣用之添加物:對苯甲醚、氫醌、鄰苯二酚、第三丁基兒茶酚、啡噻等熱聚合抑制劑;塑化劑;接著促進劑;填充劑;消泡劑;調平劑;表面調整劑;抗氧化劑;紫外線吸收劑;分散助劑;抗凝集劑;觸媒;效果促進劑;交聯劑;增黏劑等。
於本發明之光硬化性組合物中,除光聚合性不飽和化合物(A)、多官能硫醇化合物(B)、光聚合起始劑(C)、著色劑(D)以外之任意成分(其中,不包括具有乙烯性不飽和鍵之聚合性化合物及溶劑)之含量係根據其使用目的而適當選擇,並無特別限制,較佳為設為相對於上述光聚合性不飽和化合物之含量100質量份合計為50質量份以下。
本發明之光硬化性組合物中進而可併用鏈轉移劑、增感劑、界面活性劑、三聚氰胺等。
作為上述鏈轉移劑、增感劑,一般而言使用含硫原子之化合物。例如可列舉:硫代乙醇酸、硫代蘋果酸、硫代水楊酸、2-巰基丙酸、3-巰基丙酸、3-巰基丁酸、N-(2-巰基丙醯基)甘胺酸、2-巰基煙鹼酸、3-[N-(2-巰基乙基)胺甲醯基]丙酸、3-[N-(2-巰基乙基)胺基]丙
酸、N-(3-巰基丙醯基)丙胺酸、2-巰基乙磺酸、3-巰基丙磺酸、4-巰基丁磺酸、十二烷基(4-甲硫基)苯醚、2-巰基乙醇、3-巰基-1,2-丙二醇、1-巰基-2-丙醇、3-巰基-2-丁醇、巰基苯酚、2-巰基乙基胺、2-巰基咪唑、2-巰基苯并咪唑、2-巰基-3-吡啶酚、2-巰基苯并噻唑、巰基乙酸等巰基化合物,使該巰基化合物氧化所獲得之二硫醚化合物,碘乙酸、碘丙酸、2-碘乙醇、2-碘乙磺酸、3-碘丙磺酸等碘化烷基化合物,1,4-二甲基巰基苯等。
作為上述界面活性劑,可使用:全氟烷基磷酸酯、全氟烷基羧酸鹽等氟界面活性劑,高級脂肪酸鹼金屬鹽、烷基磺酸鹽、烷基硫酸鹽等陰離子系界面活性劑,高級胺氫鹵酸鹽、四級銨鹽等陽離子系界面活性劑,聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨醇酐脂肪酸酯、脂肪酸單甘油酯等非離子界面活性劑,兩性界面活性劑,聚矽氧系界面活性劑等界面活性劑。該等亦可組合使用。
作為上述三聚氰胺化合物,可列舉:(聚)羥甲基三聚氰胺、(聚)羥甲基甘脲、(聚)羥甲基苯并胍胺、(聚)羥甲基脲等氮化合物中之活性羥甲基(CH2OH基)之全部或一部分(至少2個)經烷基醚化而成之化合物。此處,作為構成烷基醚之烷基,可列舉甲基、乙基或丁基,相互可相同亦可不同。又,未經烷基醚化之羥甲基可於一分子內進行自縮合,亦可於二分子間進行縮合,其結果可形成低聚物成分。具體而言,可使用六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺、四甲氧基甲基甘脲、四丁氧基甲基甘脲等。該等之中,較佳為六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺等經烷基醚化之三聚氰胺。
本發明之光硬化性組合物可利用旋轉塗佈機、輥式塗佈機、棒式塗佈機、模具塗佈機、簾幕式塗佈機、各種印刷、浸漬等公知之方法而應用於鈉玻璃、石英玻璃、半導體基板、金屬、紙、塑膠等支持基體上。又,亦可暫時施於膜等支持基體上後轉印至其他支持基體
上,其應用方法並無限制。
又,作為使本發明之光硬化性組合物硬化時所使用之活化光之光源,可使用發出波長300~450nm之光者,例如可使用超高壓水銀、水銀蒸汽電弧、碳弧、氙弧等。
進而,藉由將雷射光用於曝光光源而不使用遮罩即由電腦等之數位資訊直接形成圖像的雷射直接刻寫法不僅可實現生產性之提高,亦可實現解像性或位置精度等之提高,因此有用,作為該雷射光,較佳地使用340~430nm之波長之光,亦可使用氬離子雷射、氦氖雷射、YAG(Yttrium Aluminum Garnet,釔-鋁-石榴石)雷射及半導體雷射等發出可見~紅外區域之光者。於使用該等雷射之情形時,可添加於可見~紅外之相應區域存在吸收之增感色素。
本發明之光硬化性組合物可用於塗料、塗佈劑、襯裏劑、油墨、抗蝕劑、液狀抗蝕劑、接著劑、印刷版、絕緣清漆、絕緣片材、積層板、印刷基板、半導體裝置用/LED(Light-Emitting Diode,發光二極體)封裝用/液晶注入口用/有機EL用/光元件用/電氣絕緣用/電子零件用/分離膜用等之密封劑、成形材料、油灰(putty)、玻璃纖維含浸劑、填縫劑、半導體用/太陽電池用等之鈍化膜、層間絕緣膜、保護膜等。
本發明之光硬化性組合物於使用黑色顏料作為著色劑之情形時,係為了形成黑矩陣而使用,該黑矩陣尤其可用於液晶顯示面板等圖像顯示裝置用之顯示器件用彩色濾光片。
上述黑矩陣係藉由如下步驟較佳地形成:(1)於基板上形成本發明之光硬化性組合物之塗膜;(2)介隔具有特定圖案形狀之遮罩對該塗膜照射活化光;(3)利用顯影液(尤其是鹼性顯影液)使曝光後之被膜顯影;(4)對顯影後之該被膜進行加熱。又,本發明之光硬化性組合物亦可用作無顯影步驟之噴墨方式組合物。
用於液晶顯示面板等之彩色濾光片之製造可使用本發明或其以外之光硬化性組合物,反覆進行上述(1)~(4)之步驟,並組合2色以上之圖案而製作。
以下,列舉實施例等更詳細地說明本發明,但本發明並不限定於該等實施例。
[製造例1]光聚合性不飽和化合物No.1之製備
添加1,1-雙[4-(2,3-環氧丙氧基)苯基]茚滿30.0g、丙烯酸7.52g、2,6-二-第三丁基-對甲酚0.080g、氯化四丁基銨0.183g及PGMEA 11.0g,於90℃下攪拌1小時,於105℃下攪拌1小時及於120℃下攪拌17小時。冷卻至室溫,添加琥珀酸酐8.11g、氯化四丁基銨0.427g及PGMEA 11.1g,於100℃下攪拌5小時。進而,添加1,1-雙[4-(2,3-環氧丙氧基)苯基]茚滿12.0g、2,6-二-第三丁基-對甲酚0.080g及PGMEA 0.600g,於90℃下攪拌90分鐘,於120℃下攪拌5小時後,添加PGMEA 24.0g,而獲得PGMEA溶液形式之光聚合性不飽和化合物No.1(Mw=4900,Mn=2250,酸值(固形物成分)47mg‧KOH/g,固形物成分44.5質量%)。
[製造例2]光聚合性不飽和化合物No.2之製備
添加1,1-雙[4-(2,3-環氧丙氧基)苯基]茚滿184g、丙烯酸58g、2,6-二-第三丁基-對甲酚0.26g、溴化四-正丁基銨0.11g及PGMEA 23g,於120℃下攪拌16小時。將反應液冷卻至室溫,添加PGMEA 35g、聯苯四甲酸二酐59g及溴化四-正丁基銨0.24g,於120℃下攪拌4小時。進而添加四氫鄰苯二甲酸酐20g,於120℃下攪拌4小時,於100℃下攪拌3小時,於80℃下攪拌4小時,於60℃下攪拌6小時,於40℃下攪拌11小時後,添加PGMEA 90g,而獲得PGMEA溶液形式之光聚合性不飽和化合物No.2(Mw=5000,Mn=2100,酸值(固形物成
分)92.7mgKOH/g,固形物成分44.4質量%)。
[製造例3]光聚合性不飽和化合物No.3之製備
添加1,1-雙[4-(2,3-環氧丙氧基)苯基]茚滿43g、丙烯酸11g、2,6-二-第三丁基-對甲酚0.05g、乙酸四丁基銨0.11g及PGMEA 23g,於120℃下攪拌16小時。冷卻至室溫,添加PGMEA 35g及聯苯四甲酸二酐9.4g,於120℃下攪拌8小時。進而添加四氫鄰苯二甲酸酐6.0g,於120℃下攪拌4小時,於100℃下攪拌3小時,於80℃下攪拌4小時,於60℃下攪拌6小時,於40℃下攪拌11小時後,添加PGMEA 29g,而獲得PGMEA溶液形式之光聚合性不飽和化合物No.3(Mw=4000,Mn=2100,酸值(固形物成分)86mgKOH/g,固形物成分44.5質量%)。
[比較製造例1]比較光聚合性不飽和化合物No.1之製造
添加9,9-雙(4-縮水甘油氧基苯基)茀75.0g、丙烯酸23.8g、2,6-二-第三丁基-對甲酚0.273g、氯化四丁基銨0.585g及PGMEA 65.9g,於90℃下攪拌1小時,於100℃下攪拌1小時,於110℃下攪拌1小時及於120℃下攪拌14小時。冷卻至室溫,添加琥珀酸酐25.9g、氯化四丁基銨0.427g及PGMEA 1.37g,於100℃下攪拌5小時。進而,添加9,9-雙(4-縮水甘油氧基苯基)茀30.0g、2,6-二-第三丁基-對甲酚0.269g及PGMEA 1.50g,於90℃下攪拌90分鐘,於120℃下攪拌4小時後,添加PGMEA 93.4g,而獲得PGMEA溶液形式之目的物即比較光聚合性不飽和化合物No.1(Mw=4190,Mn=2170,酸值(固形物成分)52mg‧KOH/g,固形物成分55.0質量%)。
[實施例1~7及比較例1~2]光硬化性組合物No.1~No.7及比較光硬化性組合物No.1~No.2之製備
依據[表1]之組成,獲得光硬化性組合物No.1~No.7及比較光硬化性組合物No.1~No.2。再者,數字表示質量份。
[表1]
A-1 光聚合性不飽和化合物No.1
A-2 光聚合性不飽和化合物No.2
A-3 光聚合性不飽和化合物No.3
A'-1 比較光聚合性不飽和化合物No.1
B-1 Karenz MT PE1(昭和電工公司製造)
B-2 Karenz MT BD1(昭和電工公司製造)
C-1 OXE-01(BASF公司製造)
C-2 OXE-02(BASF公司製造)
C-3 N-1919(ADEKA公司製造)
D-1 MA100(碳黑:三菱化學公司製造)
D-2 13M-C(鈦黑:三菱綜合材料公司製造)
E-1 Kayarad DPHA(多官能丙烯酸酯:日本化藥公司製造)
E-2 ARONIX M-315(多官能丙烯酸酯:東亞合成公司製造)
E-3 PGMEA
[評價例1~7及比較評價例1~2]
於基板上旋轉塗佈γ-縮水甘油氧基丙基甲基乙氧基矽烷並使之旋
轉乾燥後,旋轉塗佈實施例1~7中所獲得之光硬化性組合物No.1~No.7及比較例1~2中所獲得之比較光硬化性組合物No.1~No.2(1300r.p.m,50秒)並使之乾燥。於70℃下進行20分鐘之預烘烤後,塗佈聚乙烯醇5%溶液作為隔氧膜。於70℃下乾燥20分鐘後,使用特定之遮罩,使用超高壓水銀燈作為光源而進行曝光後,於2.5%碳酸鈉溶液中於25℃下浸漬30秒而顯影,充分進行水洗。水洗乾燥後,於230℃下烘烤1小時而使圖案固定。對所獲得之圖案進行以下之感度、耐熱性之評價。將結果示於[表1]。
(感度)
曝光時,將於曝光量70mJ/cm2下曝光充分者記為a,將於70mJ/cm2下曝光不充分、於100mJ/cm2下曝光者記為b,將於100mJ/cm2下曝光不充分、於150mJ/cm2下曝光者記為c。
(耐熱性試驗)
於230℃下烘烤3小時,將自初始膜厚之變化未達1%記為○,1%以上且未達5%記為△,5%以上記為×。
根據以上之結果,含有具有特定結構之光聚合性不飽和化合物的本發明之光硬化性組合物感度及耐熱性優異。因此,本發明之光硬化性組合物可用於彩色濾光片。
Claims (6)
- 一種光硬化性組合物,其含有光聚合性不飽和化合物(A)、多官能硫醇化合物(B)、光聚合起始劑(C)及著色劑(D),且該光聚合性不飽和化合物(A)具有作為如下反應產物之結構,即藉由具有使不飽和一元酸加成於下述通式(I)所表示之環氧化合物而成之結構的環氧加成化合物、與多元酸酐之酯化反應所獲得之反應產物,上述多官能硫醇化合物(B)之含量於光硬化性組合物中,為0.05~5質量%,(式中,R1、R2、R3及R4各自獨立表示氫原子、碳原子數1~5之烷基、碳原子數1~8之烷氧基、碳原子數2~5之烯基或鹵素原子,Y及Z各自獨立表示碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳烷基、碳原子數2~20之雜環基、或鹵素原子,上述烷基及芳烷基中之伸烷基部分亦可被不飽和鍵、-O-或-S-中斷,Z亦可為鄰接之Z彼此形成環,m表示0~10之整數,p表示0~4之整數,q表示0~8之整數,r表示0~4之整數,s表示0~4之整數,r與s之數之合計為2~4之整數)。
- 如請求項1之光硬化性組合物,其中多官能硫醇化合物(B)由下述通式(II)所表示,(式中,Q為碳原子數1~10之伸烷基,n表示2~6之整數,X1表示具有與n相同之價數之碳原子數1~20之飽和烴基)。
- 如請求項1之光硬化性組合物,其中光聚合起始劑(C)由下述通式(III)表示,(式中,R6及R7各自獨立表示氫原子、氰基、碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳烷基或碳原子數2~20之雜環基,R8及R9各自獨立表示氫原子、鹵素原子、硝基、氰基、羥基、羧基、R10、OR11、SR12、NR13R14、COR15、SOR16、SO2R17或CONR18R19,R8及R9亦可相互鍵結而形成環,R10、R11、R12、R13、R14、R15、R16、R17、R18及R19各自獨立表示碳原子數1~20之烷基、碳原子數6~30之芳基、碳原子數7~30之芳烷基或碳原子數2~20之雜環基,X2表示氧原子、硫原子、硒原子、CR20R21、CO、NR22或PR23,X3表示單鍵或CO,R20、R21、R22及R23各自獨立表示氫原子、碳原子數1~20之烷基、碳原子數6~30之芳基或碳原子數7~30之芳烷基,上述烷基或芳烷基中之亞甲基可經鹵素原子、硝基、氰基、羥基、羧基或雜環基取代,亦可被-O-中斷,R20、R21、R22及R23亦可各自獨立地與鄰接之任一苯環一起形成環,a表示0~4之整數,b表示0~5之整數)。
- 如請求項1之光硬化性組合物,其中上述著色劑(D)為黑色顏料。
- 一種黑矩陣,其使用如請求項4之光硬化性組合物。
- 一種彩色濾光片,其具有如請求項5之黑矩陣。
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