CN104035281A - 光固化性组合物 - Google Patents
光固化性组合物 Download PDFInfo
- Publication number
- CN104035281A CN104035281A CN201410078966.7A CN201410078966A CN104035281A CN 104035281 A CN104035281 A CN 104035281A CN 201410078966 A CN201410078966 A CN 201410078966A CN 104035281 A CN104035281 A CN 104035281A
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- Prior art keywords
- carbon number
- compound
- methyl
- alkyl
- acid
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 238000000016 photochemical curing Methods 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- 239000004593 Epoxy Substances 0.000 claims abstract description 41
- 239000003086 colorant Substances 0.000 claims abstract description 12
- 230000032050 esterification Effects 0.000 claims abstract description 6
- 238000005886 esterification reaction Methods 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 58
- 229910052799 carbon Inorganic materials 0.000 claims description 53
- 230000003287 optical effect Effects 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000000049 pigment Substances 0.000 claims description 14
- 150000003573 thiols Chemical class 0.000 claims description 14
- 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
- 125000004435 hydrogen atom Chemical group [H]* 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 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
- -1 thiol compound Chemical class 0.000 abstract description 167
- 239000002253 acid Substances 0.000 abstract description 21
- 150000008064 anhydrides Chemical class 0.000 abstract description 10
- 230000035945 sensitivity Effects 0.000 abstract description 9
- 239000003999 initiator Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 21
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 239000000470 constituent Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000975 dye Substances 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 description 10
- 239000011707 mineral Substances 0.000 description 10
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 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
- PMNLUUOXGOOLSP-UHFFFAOYSA-N alpha-mercaptopropionic acid Natural products CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 238000011156 evaluation Methods 0.000 description 8
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 8
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000006229 carbon black Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 7
- 229960005082 etohexadiol Drugs 0.000 description 7
- 239000011572 manganese Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 239000002966 varnish Substances 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000758 substrate Substances 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 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 4
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical group CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin 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
- 238000003892 spreading Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-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
- 229930185605 Bisphenol Natural products 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 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
- 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 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 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
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- VRWKTAYJTKRVCU-UHFFFAOYSA-N iron(6+);hexacyanide Chemical compound [Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] VRWKTAYJTKRVCU-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 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
- 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
- 150000000343 2,5-xylenols Chemical class 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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 2
- NXKOSHBFVWYVIH-UHFFFAOYSA-N 2-n-(butoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical class CCCCOCNC1=NC(N)=NC(N)=N1 NXKOSHBFVWYVIH-UHFFFAOYSA-N 0.000 description 2
- 150000000469 3,5-xylenols Chemical class 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
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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
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- 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
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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
- G03F7/0005—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
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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
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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
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Landscapes
- 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
本发明提供感度及耐热性优异、可获得适当图案形状或微细图案的高电阻的光固化性组合物。该光固化性组合物含有具有下述结构的光聚合性不饱和化合物(A)、多官能硫醇化合物(B)、光聚合引发剂(C)及着色剂(D),所述结构是通过具有在下述通式(I)所示的环氧化合物上加成不饱和一元酸而成的结构的环氧加成化合物与多元酸酐的酯化反应获得的反应产物的结构,式中,R1、R2、R3、R4、Y、Z、m、p、q、r、s的定义参见说明书。
Description
技术领域
本发明涉及含有具有特定结构的光聚合性不饱和化合物及多官能硫醇化合物的光固化性组合物。
背景技术
光固化性组合物是含有颜料、光聚合性不饱和化合物及光聚合引发剂的组合物。该光固化性组合物通过照射紫外线或电子射线而可以聚合固化,因此特别是在使用了黑色颜料时,由于会提高显示对比度或发色效果,因此作为设置于滤色器的R、G、B的着色层之间的边界部分上的黑色矩阵是有用的。
最近,在黑色矩阵的制造工序中,经过曝光、显影、后固化所获得的黑色图案与透明基板的密合性不充分,由于反复进行形成黑色图案的剥离工序,会将之前已形成的着色图案的一部分同时剥离,具有图案发生缺失、或曝光固化部残留在透明基板上的问题。
下述专利文献1及2中公开了含有作为光聚合引发剂的多官能硫醇和具有烯键式不饱和键的化合物的感光性组合物。另外,下述专利文献3中公开了含有粘合剂树脂、具有烯键式不饱和键的化合物、光聚合引发剂、黑色颜料、溶剂及硫醇化合物的遮光性黑色抗蚀剂组合物。但是,专利文献1及2中既未记载也未教示本发明的具有特定结构的光聚合性不饱和化合物,专利文献3中作为上述粘合剂树脂也既未记载也未教示本申请发明的具有特定结构的光聚合性不饱和化合物。另外,下述专利文献4中虽然公开了含有具有特定结构的光聚合性不饱和化合物及光聚合引发剂的碱显影性感光性树脂组合物,但既未记载也未教示并用多官能硫醇。
现有技术文献
专利文献
专利文献1:日本特开2003-252918号公报
专利文献2:日本特开2004-325735号公报
专利文献3:日本特开2004-325734号公报
专利文献4:国际公开2008-139924号公报
发明内容
发明要解决的课题
因此,本发明的目的在于提供感度及耐热性优异、能够获得适当的图案形状或微细图案的高电阻的光固化性组合物。
用于解决课题的手段
本发明人们反复进行深入研究的结果发现,含有具有下述结构的光聚合性不饱和化合物(A)、多官能硫醇化合物(B)、光聚合引发剂(C)及着色剂(D)的光固化性组合物可以实现上述目的,所述结构为具有在下述通式(I)所示的环氧化合物上加成不饱和一元酸而成的结构的环氧加成化合物与多元酸酐通过酯化反应获得的反应产物的结构,并且发现上述光聚合性组合物适于滤色器,从而完成了本发明。
(式中,R1、R2、R3及R4各自独立地表示氢原子、碳原子数为1~5的烷基、碳原子数为1~8的烷氧基、碳原子数为2~5的链烯基或者卤原子,Y及Z各自独立地表示碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳基烷基、碳原子数为2~20的杂环基或者卤原子,上述烷基及芳基烷基中的亚烷基部分可以被不饱和键、-O-或-S-中断,Z还可以相邻的Z之间形成环,m表示0~10的整数,p表示0~4的整数,q表示0~8的整数,r表示0~4的整数,s表示0~4的整数,r和s的数值之和为2~4的整数。)
另外,本发明提供使用了上述光固化性组合物的滤色器。
发明的效果
根据本发明,含有具有特定结构的光聚合性不饱和化合物的光固化性组合物的感度及耐热性优异。另外,其固化物适于显示设备用滤色器及液晶显示面板以及有机EL显示面板。
具体实施方式
以下,根据优选的实施方式说明本发明的光固化性组合物。
本发明的光固化性组合物含有具有下述结构的光聚合性不饱和化合物(A)、多官能硫醇化合物(B)、光聚合引发剂(C)及着色剂(D),所述结构为具有在上述通式(I)所示环氧化合物上加成不饱和一元酸而成的结构的环氧加成化合物与多元酸酐通过酯化反应获得的反应产物的结构。以下,依次对各成分进行说明。
<光聚合性不饱和化合物(A)>
本发明的光固化性组合物中使用的光聚合性不饱和化合物(A)具有作为具有在上述通式(I)所示的环氧化合物上加成不饱和一元酸而成的结构的环氧加成化合物与多元酸酐通过酯化反应获得的反应产物的结构。
上述通式(I)中,作为R1、R2、R3及R4所表示的碳原子数为1~5的烷基,可举出甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、异丁基、戊基、异戊基、叔戊基等。
作为R1、R2、R3及R4所表示的碳原子数为1~8的烷氧基,可举出甲氧基、乙氧基、异丙氧基、丙氧基、丁氧基、戊氧基、异戊氧基、己氧基、庚氧基、辛氧基、2-乙基己氧基等。
作为R1、R2、R3及R4所表示的碳原子数为2~5的链烯基,可举出乙烯基、烯丙基、丁烯基、丙烯基等。
作为R1、R2、R3及R4所表示的卤原子,可举出氟原子、氯原子、溴原子、碘原子。
上述通式(I)中,作为Y及Z所表示的碳原子数为1~20的烷基,除了上述R1、R2、R3及R4所示例的烷基之外,还可举出己基、庚基、异庚基、叔庚基、正辛基、异辛基、叔辛基、2-乙基己基、正壬基、正癸基、三氟甲基、二氟甲基、单氟甲基、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、环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基、环癸基等。
作为Y及Z所表示的碳原子数为6~30的芳基,可举出苯基、萘基、蒽-1-基、菲-1-基、邻甲苯基、间甲苯基、对甲苯基、4-乙烯基苯基、3-异丙基苯基、4-异丙基苯基、4-丁基苯基、4-异丁基苯基、4-叔丁基苯基、4-己基苯基、4-环己基苯基、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、2,4-二叔丁基苯基、3,5-二叔丁基苯基、2,6-二叔丁基苯基、2,4-二叔戊基苯基、2,5-二叔戊基苯基、环己基苯基、联苯基、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。
作为Y及Z所表示的碳原子数为7~30的芳基烷基,可举出苄基、苯乙基、2-苯基丙基、二苯基甲基、三苯基甲基、苯乙烯基、肉桂基、4-氯苯基甲基等。
作为Y及Z所表示的杂环基,可举出吡咯基、吡啶基、嘧啶基、哒嗪基、哌嗪基、哌啶基、吡喃基、吡唑基、三嗪基、吡咯烷基、喹啉基、异喹啉基、咪唑基、苯并咪唑基、三唑基、呋喃基、呋喃基、苯并呋喃基、噻吩基、苯硫基、苯并噻吩基、噻二唑基、噻唑基、苯并噻唑基、噁唑基、苯并噁唑基、异噻唑基、异噁唑基、吲哚基、久洛尼定基、吗啉基、硫代吗啉基、2-吡咯烷酮-1-基、2-哌啶酮-1-基、2,4-二氧代咪唑烷-3-基、2,4-二氧代噁唑烷-3-基等。
在上述通式(I)所示的环氧化合物中,从进一步提高本发明的效果的观点出发,优选r和s之和为2或3的整数的化合物,更优选r和s之和为2的化合物,特别优选r为0且s为2的化合物。
作为作用于上述环氧化合物的环氧基的上述不饱和一元酸,可举出丙烯酸、甲基丙烯酸、巴豆酸、肉桂酸、山梨酸、甲基丙烯酸·马来酸羟基乙酯、丙烯酸·马来酸羟基乙酯、甲基丙烯酸·马来酸羟基丙酯、丙烯酸·马来酸羟基丙酯、双环戊二烯·马来酸酯等。
另外,作为在加成上述不饱和一元酸后发生酯化反应的上述多元酸酐,可举出联苯四羧酸二酐、四氢邻苯二甲酸酐、琥珀酸酐、马来酸酐、偏苯三酸酐、均苯四酸酐、2,2’-3,3’-二苯甲酮四羧酸酐、乙二醇双(脱水偏苯三酸酯)、甘油三(脱水偏苯三酸酯)、六氢邻苯二甲酸酐、甲基四氢邻苯二甲酸酐、纳迪克酸酐、甲基纳迪克酸酐、三烷基四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、5-(2,5-二氧代四氢呋喃基)-3-甲基-3-环己烯-1,2-二羧酸酐、三烷基四氢邻苯二甲酸酐-马来酸酐加成物、十二碳烯基琥珀酸酐、甲基降冰片烯二酸酐等。
上述环氧化合物、上述不饱和一元酸及上述多元酸酐的反应摩尔比优选如下所述。
即,对于具有相对于上述环氧化合物的1个环氧基加成0.1~1.0个上述不饱和一元酸的羧基而成的结构的环氧加成物,优选达到相对于该环氧加成物的1个羟基、上述多元酸酐的酸酐结构成为0.1~1.0个的比例。
上述环氧化合物、上述不饱和一元酸及上述多元酸酐的反应可按照常规方法进行。
从进一步提高本发明的效果的观点出发,上述光聚合性不饱和化合物(A)的数均分子量Mn优选为300~5000、更优选为500~2500。另外,上述光聚合性不饱和化合物(A)的固体成分的酸值优选为20~100mgKOH/g、更优选为40~100mgKOH/g。
本发明的光固化性组合物中,上述光聚合性不饱和化合物(A)的含量在本发明的光固化性组合物的固体成分中优选为5~80质量%、特别优选为10~40质量%。光聚合性不饱和化合物的含量少于5质量%时,有时会引起固化不良,光聚合性不饱和化合物的含量多于80质量%时,有时无法获得充分的遮光性。
<多官能硫醇化合物(B)>
作为本发明的光固化性组合物中使用的多官能硫醇化合物(B),可以使用现有公知的物质,特别地从耐热性的方面出发优选下述通式(II)所示的物质。
(式中,Q是碳原子数为1~10的亚烷基、n表示2~6的整数、X1表示具有与n相同价数的碳原子数为1~20的饱和烃基。)
上述通式(II)中,作为X1表示的碳原子数为1~20的饱和烃基,可举出在上述通式(I)的说明中作为上述碳原子数为1~20的烷基所示例的基团。
作为Q所表示的碳原子数为1~10的亚烷基,可举出亚甲基、亚乙基、亚丙基、甲基亚乙基、亚丁基、1-甲基亚丙基、2-甲基亚丙基、1,2-二甲基亚丙基、1,3-甲基亚丙基、1-甲基亚丁基、2-甲基亚丁基、3-甲基亚丁基、2,4-二甲基亚丁基、1,3-二甲基亚烯基、亚戊基、亚己基、亚庚基、亚辛基、乙烷-1,1-二基、丙烷-2,2-二基等。
上述通式(II)中,从耐热性的方面出发优选n为2或4。另外,从感度的方面出发,n优选为3以上、特别优选为4以上。
作为上述通式(II)所示的化合物,例如可举出1,4-双(3-巯基丁酰基氧基)丁烷、乙二醇双(3-巯基丁酸酯)、二乙二醇双(3-巯基丁酸酯)、丁二醇双(3-巯基丁酸酯)、辛二醇双(3-巯基丁酸酯)、壬二醇双(3-巯基丁酸酯)、季戊四醇四(3-巯基丁酸酯)、二季戊四醇六(3-巯基丁酸酯)、乙二醇双(2-巯基丙酸酯)、二乙二醇双(2-巯基丙酸酯)、丁二醇双(2-巯基丙酸酯)、辛二醇双(2-巯基丙酸酯)、壬二醇双(2-巯基丙酸酯)、季戊四醇四(2-巯基丙酸酯)、二季戊四醇六(2-巯基丙酸酯)、乙二醇双(3-巯基异丁酸酯)、二乙二醇双(3-巯基异丁酸酯)、丁二醇双(3-巯基异丁酸酯)、辛二醇双(3-巯基异丁酸酯)、壬二醇双(3-巯基异丁酸酯)、二季戊四醇六(3-巯基异丁酸酯)、乙二醇双(2-巯基异丁酸酯)、二乙二醇双(2-巯基异丁酸酯)、丁二醇双(2-巯基异丁酸酯)、辛二醇双(2-巯基异丁酸酯)、壬二醇双(2-巯基异丁酸酯)、季戊四醇四(2-巯基异丁酸酯)、二季戊四醇六(2-巯基异丁酸酯)、乙二醇双(4-巯基戊酸酯)、二乙二醇双(4-巯基戊酸酯)、丁二醇双(4-巯基戊酸酯)、辛二醇双(4-巯基戊酸酯)、壬二醇双(4-巯基戊酸酯)、季戊四醇四(4-巯基戊酸酯)、二季戊四醇六(4-巯基戊酸酯)、乙二醇双(3-巯基戊酸酯)、二乙二醇双(3-巯基戊酸酯)、丁二醇双(3-巯基戊酸酯)、辛二醇双(3-巯基戊酸酯)、壬二醇双(3-巯基戊酸酯)、季戊四醇四(3-巯基戊酸酯)、二季戊四醇六(3-巯基戊酸酯)等。
作为多官能硫醇化合物(B),除了上述通式(II)所示的化合物之外,还可使用2-(N,N-二丁基氨基)-4,6-二巯基-s-三嗪、2,5-己烷二硫醇、2,9-癸烷二硫醇、1,4-双(1-巯基乙基)苯等。
本发明的光固化性组合物中,上述多官能硫醇化合物(B)的含量在本发明的光固化性组合物中优选为0.05~5质量%、特别优选为0.5~5质量%。上述多官能硫醇化合物的含量少于0.05质量%时,有时利用曝光进行的固化变得不充分,而多于5质量%时,有时光固化性不饱和化合物与多官能硫醇化合物容易发生反应、保存稳定性变差、发生凝胶化。
<光聚合引发剂(C)>
作为本发明的光固化性组合物中使用的光聚合引发剂(C),可以使用现有公知的化合物,例如可举出二苯甲酮、苯基联苯酮、1-羟基-1-苯甲酰基环己烷、4-苯甲酰基-4’-甲基二苯基硫化物、苯偶姻丁基醚、2-羟基-2-苯甲酰基丙烷、2-羟基-2-(4’-异丙基)苯甲酰基丙烷、4-丁基苯甲酰基三氯甲烷、4-苯氧基苯甲酰基二氯甲烷、苯甲酰基甲酸甲酯、苯偶姻、2-吗啉基-2-(4’-甲基巯基)苯甲酰基丙烷、2,2-二甲氧基-1,2-二苯基乙烷-1-酮、1-苄基-1-二甲基氨基-1-(4’-吗啉代苯甲酰基)丙烷等烷基苯酮系化合物;1,2-辛二酮、1-[4-(苯基硫代)-2-(O-苯甲酰基肟)]、乙酮、1-[9-乙基-6-(2-甲基苯甲酰基)-9H-咔唑-3-基]-,1-(O-乙酰基肟)等肟酯化合物;噻吨酮、1-氯-4-丙氧基噻吨酮、异丙基噻吨酮、二乙基噻吨酮等噻吨酮化合物;乙基蒽醌等蒽醌化合物;2,2-双(2-氯苯基)-4,5,4’,5’-四苯基-1-2’-联咪唑等联咪唑化合物;2-甲基-4,6-双(三氯甲基)-s-三嗪、2-苯基-4,6-双(三氯甲基)-s-三嗪、2-萘基-4,6-双(三氯甲基)-s-三嗪等三嗪化合物;4,4-偶氮双异丁腈等偶氮化合物;过氧化苯甲酰等过氧化物;1,7-双(9’-吖啶基)庚烷、9-正丁基-3,6-双(2’-吗啉代异丁酰氧基)咔唑、三苯基膦、樟脑醌等,作为市售品可举出N-1414、N-1717、N-1919、PZ-808、NCI-831、NCI-930(株式会社ADEKA公司制)、IRGACURE184、IRGACURE369、IRGACURE651、IRGACURE907、IRGACURE OXE01、IRGACURE OXE02(BASF株式会社公司制)等。
作为本发明的光固化性组合物中使用的光聚合引发剂,从感度及耐热性的方面出发,特别优选下述通式(III)所示的化合物。
(式中,R6及R7各自独立地表示氢原子、氰基、碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳基烷基或碳原子数为2~20的杂环基,
R8及R9各自独立地表示氢原子、卤原子、硝基、氰基、羟基、羧基、R10、OR11、SR12、NR13R14、COR15、SOR16、SO2R17或CONR18R19,R8及R9还可相互键合形成环,
R10、R11、R12、R13、R14、R15、R16、R17、R18、R19各自独立地表示碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳基烷基或碳原子数为2~20的杂环基,
X2表示氧原子、硫原子、硒原子、CR20R21、CO、NR22或PR23,
X3表示单键或CO,
R20、R21、R22及R23各自独立地表示氢原子、碳原子数为1~20的烷基、碳原子数为6~30的芳基或碳原子数为7~30的芳基烷基,上述烷基或芳基烷基中的亚甲基还可以被卤原子、硝基、氰基、羟基、羧基或杂环基取代,也可以被-O-中断,
R20、R21、R22及R23各自独立地可以与相邻的任一个苯环一起形成环,
a表示0~4的整数,
b表示0~5的整数。)
本发明的光固化性组合物中,上述光聚合引发剂的含量在本发明的光固化性组合物的固体成分中优选为0.1~30质量%、特别优选为0.5~10质量%。上述光聚合引发剂的含量少于0.1质量%时,有时利用曝光进行的固化变得不充分,多于30质量%时,有时引发剂会析出至树脂组合物中。
<着色剂(D)>
作为本发明的光固化性组合物中使用的着色剂(D),可以使用无机色料或有机色料,它们可单独使用或者混合2种以上使用。
作为上述无机色料或有机色料,例如可以使用亚硝基化合物、硝基化合物、偶氮化合物、重氮化合物、呫吨化合物、喹啉化合物、蒽醌化合物、香豆素化合物、酞菁化合物、异吲哚满酮化合物、异吲哚满化合物、喹吖酮化合物、蒽嵌蒽二酮化合物、紫环酮化合物、苝化合物、二酮吡咯并吡咯化合物、硫靛化合物、二噁嗪化合物、三苯基甲烷化合物、喹酞酮化合物、萘四羧酸;偶氮染料、菁染料等金属络合物化合物;色淀颜料;通过炉法、槽法、热裂法获得的炭黑、或者乙炔黑、科琴黑或灯黑等炭黑;用环氧树脂对上述炭黑进行了调整、包覆的物质,预先在溶剂中用树脂对上述炭黑进行分散处理、吸附了20~200mg/g的树脂的物质,对上述炭黑进行了酸性或碱性表面处理的物质,平均粒径为8nm以上且DBP吸油量为90ml/100g以下的物质,由950℃下的挥发成分中的CO、CO2算出的总氧量相对于炭黑的每100m2表面积为9mg以上的物质;石墨、石墨化炭黑、活性炭、碳纤维、碳纳米管、微米螺旋碳、碳纳米角、碳气凝胶、富勒烯;苯胺黑、颜料黑7、钛黑;合成铁黑;疏水性树脂、氧化铬绿、密罗里蓝、钴绿、钴蓝、锰系、亚铁氰化物、磷酸盐群青、普鲁士蓝、群青、赛璐里安蓝、维利迪安颜料、翡翠绿、硫酸铅、黄色铅、锌黄、氧化铁红(红色氧化铁(III))、镉红、昂伯等无机颜料或有机颜料。
作为上述无机色料或有机色料,还可使用市售的颜料,例如可举出颜料红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;颜料橙13、31、34、36、38、43、46、48、49、51、52、55、59、60、61、62、64、65、71;颜料黄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;颜料绿7、10、36;颜料蓝15、15:1、15:2、15:3、15:4、15:5、15:6、22、24、56、60、61、62、64;颜料紫1、19、23、27、29、30、32、37、40、50等。
作为上述无机色料或有机色料,还可使用公知的染料。作为公知的染料,例如可举出偶氮染料、蒽醌染料、靛类染料、三芳基甲烷染料、呫吨染料、茜素染料、吖啶染料、1,2-二苯乙烯染料、噻唑染料、萘酚染料、喹啉染料、硝基染料、吲达胺染料、噁嗪染料、酞菁染料、菁染料等染料等。
本发明的光固化性组合物中,上述着色剂(D)的含量相对于含有上述光聚合性不饱和化合物的具有烯键式不饱和键的聚合性化合物整体100质量份优选为0~350质量份、更优选为0~300质量份、进一步优选为0~250质量份。超过350质量份时,着色剂变得易于凝聚,保存稳定性变差。
本发明的光固化性组合物中,还可进一步使用除光聚合性不饱和化合物(A)以外的具有烯键式不饱和键的聚合性化合物。作为该具有烯键式不饱和键的聚合性化合物并无特别限定,可以使用以往在感光性组合物中使用的物质,例如可举出乙烯、丙烯、丁烯、异丁烯、氯乙烯、偏氯乙烯、偏氟乙烯、四氟乙烯等不饱和脂肪族烃;(甲基)丙烯酸、α-氯丙烯酸、衣康酸、马来酸、柠康酸、富马酸、降冰片烯二酸、巴豆酸、异巴豆酸、醋酸乙烯酯、醋酸烯丙酯、肉桂酸、山梨酸、中康酸、琥珀酸单[2-(甲基)丙烯酰氧基乙基]酯、邻苯二甲酸单[2-(甲基)丙烯酰氧基乙基]酯、ω-羧基聚己内酯单(甲基)丙烯酸酯等在两末端具有羧基和羟基的聚合物的单(甲基)丙烯酸酯;(甲基)丙烯酸·马来酸羟基乙酯、(甲基)丙烯酸·马来酸羟基丙酯、双环戊二烯·马来酸酯或具有1个羧基和2个以上(甲基)丙烯酰基的多官能(甲基)丙烯酸酯等不饱和一元酸;(甲基)丙烯酸-2-羟基乙酯、(甲基)丙烯酸-2-羟基丙酯、(甲基)丙烯酸缩水甘油酯、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)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸异辛酯、(甲基)丙烯酸异壬酯、(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)丙烯酸二甲基氨基甲酯、(甲基)丙烯酸二甲基氨基乙酯、(甲基)丙烯酸氨基丙酯、(甲基)丙烯酸二甲基氨基丙酯、(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)丙烯酸丙烯酸乙基己酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸四氢呋喃酯、(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、三羟甲基乙烷三(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、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、三环癸烷二羟甲基二(甲基)丙烯酸酯、三[(甲基)丙烯酰基乙基]异氰脲酸酯、聚酯(甲基)丙烯酸酯低聚物等不饱和一元酸与多元醇或多元酚的酯;(甲基)丙烯酸锌、(甲基)丙烯酸镁等不饱和多元酸的金属盐;马来酸酐、衣康酸酐、柠康酸酐、甲基四氢邻苯二甲酸酐、四氢邻苯二甲酸酐、三烷基四氢邻苯二甲酸酐、5-(2,5-二氧代四氢呋喃基)-3-甲基-3-环己烯-1,2-二羧酸酐、三烷基四氢邻苯二甲酸酐-马来酸酐加成物、十二碳烯基琥珀酸酐、甲基降冰片烯二酸酐等不饱和多元酸的酸酐;(甲基)丙烯酰胺、亚甲基双(甲基)丙烯酰胺、二乙撑三胺三(甲基)丙烯酰胺、亚二甲苯基双(甲基)丙烯酰胺、α-氯丙烯酰胺、N-2-羟基乙基(甲基)丙烯酰胺等不饱和一元酸与多元胺的酰胺;丙烯醛等不饱和醛;(甲基)丙烯腈、α-氯丙烯腈、偏二氰乙烯、烯丙基氰等不饱和腈;苯乙烯、4-甲基苯乙烯、4-乙基苯乙烯、4-甲氧基苯乙烯、4-羟基苯乙烯、4-氯苯乙烯、二乙烯基苯、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、乙烯基苄基甲基醚、乙烯基苄基缩水甘油基醚等不饱和芳香族化合物;甲基乙烯基酮等不饱和酮;乙烯基胺、烯丙基胺、N-乙烯基吡咯烷酮、乙烯基哌啶等不饱和胺化合物;烯丙基醇、巴豆醇等乙烯基醇;乙烯基甲基醚、乙烯基乙基醚、正丁基乙烯基醚、异丁基乙烯基醚、烯丙基缩水甘油基醚等乙烯基醚;马来酰亚胺、N-苯基马来酰亚胺、N-环己基马来酰亚胺等不饱和酰亚胺类;茚、1-甲基茚等茚类;1,3-丁二烯、异戊二烯、氯丁二烯等脂肪族共轭二烯类;聚苯乙烯、聚(甲基)丙烯酸甲酯、聚(甲基)丙烯酸正丁酯、聚硅氧烷等在聚合物分子链的末端具有单(甲基)丙烯酰基的大分子单体类;氯乙烯、偏氯乙烯、琥珀酸二乙烯酯、邻苯二甲酸二烯丙基酯、磷酸三烯丙基酯、异氰脲酸三烯丙基酯、乙烯基硫代醚、乙烯基咪唑、乙烯基噁唑啉、乙烯基咔唑、乙烯基吡咯烷酮、乙烯基吡啶、含羟基的乙烯基单体及聚异氰酸酯化合物的乙烯基氨基甲酸酯化合物、含羟基的乙烯基单体及聚环氧化合物的乙烯基环氧化合物。
化合物No.A1
化合物No.A2
化合物No.A3
化合物No.A4
另外,作为上述具有烯键式不饱和键的聚合性化合物,还可以使用丙烯酸酯的共聚物、苯酚和/或甲酚酚醛清漆环氧树脂、具有多官能环氧基的聚苯基甲烷型环氧树脂。
上述具有烯键式不饱和键的聚合性化合物中,在使用具有酸值的化合物时,可以对本发明的光固化性组合物赋予碱显影性。使用上述具有酸值的化合物时,其使用量优选达到上述具有烯键式不饱和键的聚合性化合物整体的50~99质量%的量。
另外,上述具有酸值的化合物还可在通过使单官能或多官能环氧化合物发生反应而进行酸值调整后进行使用。通过调整上述具有酸值的化合物的酸值,可以改良感光性树脂的碱显影性。上述具有酸值的化合物(即赋予碱显影性的具有烯键式不饱和键的聚合性化合物)优选固体成分的酸值为5~120mgKOH/g的范围,单官能或多官能环氧化合物的使用量优选按照满足上述酸值的方式进行选择。
作为上述单官能环氧化合物,可举出甲基丙烯酸缩水甘油酯、甲基缩水甘油基醚、乙基缩水甘油基醚、丙基缩水甘油基醚、异丙基缩水甘油基醚、丁基缩水甘油基醚、异丁基缩水甘油基醚、叔丁基缩水甘油基醚、戊基缩水甘油基醚、己基缩水甘油基醚、庚基缩水甘油基醚、辛基缩水甘油基醚、壬基缩水甘油基醚、癸基缩水甘油基醚、十一烷基缩水甘油基醚、十二烷基缩水甘油基醚、十三烷基缩水甘油基醚、十四烷基缩水甘油基醚、十五烷基缩水甘油基醚、十六烷基缩水甘油基醚、2-乙基己基缩水甘油基醚、烯丙基缩水甘油基醚、炔丙基缩水甘油基醚、对甲氧基乙基缩水甘油基醚、苯基缩水甘油基醚、对甲氧基缩水甘油基醚、对丁基苯酚缩水甘油基醚、甲苯基缩水甘油基醚、2-甲基甲苯基缩水甘油基醚、4-壬基苯基缩水甘油基醚、苄基缩水甘油基醚、对枯基苯基缩水甘油基醚、三苯甲基缩水甘油基醚、2,3-环氧丙基甲基丙烯酸酯、环氧化大豆油、环氧化亚麻籽油、丁酸缩水甘油酯、乙烯基环己烷单氧化物、1,2-环氧-4-乙烯基环己烷、苯乙烯氧化物、蒎烯氧化物、甲基苯乙烯氧化物、环己烯氧化物、环氧丙烷、上述化合物No.A2、No.A3等。
作为上述多官能环氧化合物,当使用选自双酚型环氧化合物及缩水甘油基醚中的1种以上的化合物时,由于可以获得特性更为良好的光固化性组合物,因此优选。
作为上述双酚型环氧化合物,除了可以使用上述通式(I)所示的环氧化合物之外,例如还可使用氢化双酚型环氧化合物等双酚型环氧化合物。
另外,作为上述缩水甘油基醚类,可以使用乙二醇二缩水甘油基醚、丙二醇二缩水甘油基醚、1,4-丁二醇二缩水甘油基醚、1,6-己二醇二缩水甘油基醚、1,8-辛二醇二缩水甘油基醚、1,10-癸二醇二缩水甘油基醚、2,2-二甲基-1,3-丙二醇二缩水甘油基醚、二乙二醇二缩水甘油基醚、三乙二醇二缩水甘油基醚、四乙二醇二缩水甘油基醚、六乙二醇二缩水甘油基醚、1,4-环己烷二甲醇二缩水甘油基醚、1,1,1-三(缩水甘油氧基甲基)丙烷、1,1,1-三(缩水甘油氧基甲基)乙烷、1,1,1-三(缩水甘油氧基甲基)甲烷、1,1,1,1-四(缩水甘油氧基甲基)甲烷等。
除此以外,还可使用苯酚酚醛清漆型环氧化合物、联苯酚醛清漆型环氧化合物、甲酚酚醛清漆型环氧化合物、双酚A酚醛清漆型环氧化合物、双环戊二烯酚醛清漆型环氧化合物等酚醛清漆型环氧化合物;3,4-环氧-6-甲基环己基甲基-3,4-环氧-6-甲基环己烷羧酸酯、3,4-环氧环己基甲基-3,4-环氧环己烷羧酸酯、1-环氧乙基-3,4-环氧环己烷等脂环式环氧化合物;邻苯二甲酸二缩水甘油酯、四氢邻苯二甲酸二缩水甘油酯、二聚物酸缩水甘油酯等缩水甘油酯类;四缩水甘油基二氨基二苯基甲烷、三缩水甘油基对氨基苯酚、N,N-二缩水甘油基苯胺等缩水甘油基胺类;1,3-二缩水甘油基-5,5-二甲基乙内酰脲、三缩水甘油基异氰脲酸酯等杂环式环氧化合物;双环戊二烯二氧化物等二氧化物化合物;萘型环氧化合物;三苯基甲烷型环氧化合物;双环戊二烯型环氧化合物等。
另外,本发明的光固化性组合物还可以含有不具有烯键式不饱和键的赋予碱显影性的化合物,作为这种化合物,只要是通过具有酸值即可溶解于碱水溶液中的化合物,则无特别限定,作为代表性的化合物可举出碱可溶性酚醛清漆树脂(以下仅称作“酚醛清漆树脂”)。酚醛清漆树脂通过在酸催化剂的存在下将酚类和醛类缩聚而获得。
作为上述酚类,例如可使用苯酚、邻甲酚、间甲酚、对甲酚、邻乙基苯酚、间乙基苯酚、对乙基苯酚、邻丁基苯酚、间丁基苯酚、对丁基苯酚、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、对苯基苯酚、氢醌、儿茶酚、间苯二酚、2-甲基间苯二酚、焦棓酚、α-萘酚、双酚A、二羟基苯甲酸酯、没食子酸酯等,这些酚类中优选苯酚、邻甲酚、间甲酚、对甲酚、2,5-二甲苯酚、3,5-二甲苯酚、2,3,5-三甲基苯酚、间苯二酚、2-甲基间苯二酚及双酚A。这些酚类可单独使用或者混合2种以上使用。
作为上述醛类,例如可使用甲醛、多聚甲醛、乙醛、丙醛、苯甲醛、苯乙醛、α-苯丙醛、β-苯丙醛、邻羟基苯甲醛、间羟基苯甲醛、对羟基苯甲醛、邻氯苯甲醛、间氯苯甲醛、对氯苯甲醛、邻硝基苯甲醛、间硝基苯甲醛、对硝基苯甲醛、邻甲基苯甲醛、间甲基苯甲醛、对甲基苯甲醛、对乙基苯甲醛、对正丁基苯甲醛等。这些化合物中优选甲醛、乙醛及苯甲醛。这些醛类可单独使用或者混合2种以上使用。醛类以相对于酚类每1摩尔优选为0.7~3摩尔、特别优选为0.7~2摩尔的比例进行使用。
作为上述酸催化剂,例如使用盐酸、硝酸、硫酸等无机酸或甲酸、草酸、乙酸等有机酸。这些酸催化剂的使用量相对于酚类每1摩尔优选为1×10-4~5×10-1摩尔。在缩合反应中,通常使用水作为反应介质,但当缩合反应中使用的酚类不溶解于醛类的水溶液中、从反应初期开始变成不均匀体系的情况下,还可使用亲水性溶剂作为反应介质。作为这些亲水性溶剂,例如可举出甲醇、乙醇、丙醇、丁醇等醇类或四氢呋喃、二噁烷等环状醚类。这些反应介质的使用量通常相对于反应原料每100质量份为20~1000质量份。缩合反应的反应温度可根据反应原料的反应性适当调整,通常为10~200℃、优选为70~150℃。缩合反应结束后,为了将存在于体系内的未反应原料、酸催化剂及反应介质除去,通常将内温上升至130~230℃,在减压下将挥发成分蒸馏除去,接着将熔融了的酚醛清漆树脂流延至钢制传送带等上来进行回收。
另外,还可在缩合反应结束后,通过将反应混合物溶解在上述亲水性溶剂中并添加在水、正己烷、正庚烷等沉淀剂中,使酚醛清漆树脂析出,将析出物分离并进行加热干燥,从而进行回收。
作为除上述酚醛清漆树脂以外的例子,可举出聚羟基苯乙烯或其衍生物、苯乙烯-马来酸酐共聚物、聚乙烯基羟基苯甲酸酯等。
本发明的光固化性组合物中还可添加溶剂。作为该溶剂,可举出通常根据需要能够溶解或分散上述各成分(本发明的光聚合性不饱和化合物(A))、多官能硫醇化合物(B)、光聚合引发剂(C)、着色剂(D)等)的溶剂,例如甲乙酮、甲基戊基酮、二乙基酮、丙酮、甲基异丙基酮、甲基异丁基酮、环己酮、2-庚酮等酮类;乙基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二丙二醇二甲基醚等醚系溶剂;乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸正丁酯、乙酸环己酯、乳酸乙酯、琥珀酸二甲酯、Texanol醇酯等酯系溶剂;乙二醇单甲基醚、乙二醇单乙基醚等溶纤剂系溶剂;甲醇、乙醇、异或正丙醇、异或正丁醇、戊醇等醇系溶剂;乙二醇单甲基乙酸酯、乙二醇单乙基乙酸酯、丙二醇-1-单甲基醚-2-乙酸酯(PGMEA)、二丙二醇单甲基醚乙酸酯、3-甲氧基丁基乙酸酯、乙氧基乙基丙酸酯等醚酯系溶剂;苯、甲苯、二甲苯等BTX系溶剂;己烷、庚烷、辛烷、环己烷等脂肪族烃系溶剂;松节油、D-柠檬烯、蒎烯等萜烯系烃油;矿油精、スワゾール#310(Cosmo松山石油株式会社)、ソルベッソ#100(Exon化学株式会社)等链烷烃系溶剂,四氯化碳、氯仿、三氯乙烯、二氯甲烷、1,2-二氯乙烷等卤代脂肪族烃系溶剂;氯苯等卤代芳香族烃系溶剂;卡必醇系溶剂、苯胺、三乙基胺、吡啶、乙酸、乙腈、二硫化碳、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、二甲基亚砜、水等,这些溶剂可使用1种或者作为2种以上的混合溶剂进行使用。其中,酮类、醚酯系溶剂等、特别是丙二醇-1-单甲基醚-2-乙酸酯(PGMEA)、环己酮等由于在光固化性组合物中抗蚀剂与光聚合引发剂的相容性良好,因此优选。
本发明的光固化性组合物中,上述溶剂的使用量优选使得溶剂以外的组合物的浓度达到5~30质量%,少于5质量%时,难以增厚膜厚、无法充分地吸收所希望的波长光,因此不优选,超过30质量%时,因组合物的析出导致组合物的保存性降低或粘度提高,因此操作性降低,因而不优选。
本发明的光固化性组合物中还可进一步含有无机化合物。作为该无机化合物,例如可举出氧化镍、氧化铁、氧化铱、氧化钛、氧化锌、氧化镁、氧化钙、氧化钾、二氧化硅、氧化铝等金属氧化物;层状粘土矿物、密罗里蓝、碳酸钙、碳酸镁、钴系、锰系、玻璃粉、云母、滑石、高岭土、亚铁氰化物、各种金属硫酸盐、硫化物、硒化物、硅酸铝、硅酸钙、氢氧化铝、铂、金、银、铜等,其中优选氧化钛、二氧化硅、层状粘土矿物、银等。本发明的光固化性组合物中,无机化合物的含量相对于上述光聚合性不饱和化合物100质量份优选为0.1~50质量份、更优选为0.5~20质量份,这些无机化合物可使用1种或者使用2种以上。
通过在本发明的光固化性组合物中含有无机化合物,可以制成感光性糊料组合物进行使用。该感光性糊料组合物可用于形成等离子体显示器面板的隔壁图案、电介质图案、电极图案及黑色矩阵图案等烧成物图案。
另外,这些无机化合物例如还优选作为填充剂、防反射剂、导电剂、稳定剂、阻燃剂、机械强度提高剂、特殊波长吸收剂、疏油墨剂等来使用。
本发明的光固化性组合物中,当使用颜料或无机化合物时,可以添加分散剂。作为该分散剂,只要是能够分散、稳定化无机化合物,则可以是任何分散剂,可以使用市售的分散剂、例如BYK-Chemie公司制BYK系列等,优选使用具有碱性官能团的聚酯、聚醚、聚氨酯构成的高分子分散剂、具有氮原子作为碱性官能团、具有氮原子的官能团为胺和/或其季铵盐、胺值为1~100mgKOH/g的物质。
另外,本发明的光固化性组合物中,还可根据需要添加对苯甲醚、氢醌、邻苯二酚、叔丁基儿茶酚、吩噻嗪等热聚合抑制剂;增塑剂;粘合促进剂;填充剂;消泡剂;流平剂;表面调节剂;抗氧化剂;紫外线吸收剂;分散助剂;抗凝剂;催化剂、效果促进剂;交联剂;增粘剂等常用的添加物。
本发明的光固化性组合物中,除光聚合性不饱和化合物(A)、多官能硫醇化合物(B)、光聚合引发剂(C)、着色剂(D)以外的任意成分(但具有烯键式不饱和键的聚合性化合物及溶剂除外)的含量根据其使用目的适当选择,并无特别限定,优选相对于上述光聚合性不饱和化合物的含量100质量份,合计为50质量份以下。
本发明的光固化性组合物中还可进一步并用链转移剂、增感剂、表面活性剂、三聚氰胺等。
作为上述链转移剂、增感剂,通常使用含硫原子的化合物。例如可举出硫代乙醇酸、硫代苹果酸、硫代水杨酸、2-巯基丙酸、3-巯基丙酸、3-巯基丁酸、N-(2-巯基丙酰基)甘氨酸、2-巯基烟酸、3-[N-(2-巯基乙基)氨基甲酰基]丙酸、3-[N-(2-巯基乙基)氨基]丙酸、N-(3-巯基丙酰基)丙氨酸、2-巯基乙磺酸、3-巯基丙磺酸、4-巯基丁磺酸、十二烷基(4-甲基硫代)苯基醚、2-巯基乙醇、3-巯基-1,2-丙二醇、1-巯基-2-丙醇、3-巯基-2-丁醇、巯基苯酚、2-巯基乙基胺、2-巯基咪唑、2-巯基苯并咪唑、2-巯基-3-吡硫醇、2-巯基苯并噻唑、巯基乙酸等巯基化合物,将该巯基化合物氧化获得的二硫化物化合物、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、1,4-二甲基巯基苯等。
作为上述表面活性剂,可以使用全氟烷基磷酸酯、全氟烷基羧酸盐等氟表面活性剂,高级脂肪酸碱盐、烷基磺酸盐、烷基硫酸盐等阴离子系表面活性剂,高级胺卤酸盐、季铵盐等阳离子系表面活性剂,聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨糖醇酐脂肪酸酯、脂肪酸单甘油酯等非离子表面活性剂,两性表面活性剂,有机硅系表面活性剂等表面活性剂,它们还可组合使用。
作为上述三聚氰胺化合物,可举出(聚)羟甲基三聚氰胺、(聚)羟甲基甘脲、(聚)羟甲基苯并鸟粪胺、(聚)羟甲基脲等氮化合物中的活性羟甲基(CH2OH基)的全部或一部分(至少2个)经烷基醚化的化合物。这里,作为构成烷基醚的烷基,可举出甲基、乙基或丁基,可相互相同或不同。另外,未经烷基醚化的羟甲基可以在一分子内自缩合,也可在两分子之间缩合、结果形成低聚物成分。具体地说,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。其中,优选六甲氧基甲基三聚氰胺、六丁氧基甲基三聚氰胺等经烷基醚化的三聚氰胺。
本发明的光固化性组合物可利用旋涂机、辊涂机、棒涂机、模涂机、帘式涂布机、各种印刷、浸渍等的公知手段应用于钠玻璃、石英玻璃、半导体基板、金属、纸、塑料等支撑基体上。另外,也可在暂时施于膜等支撑基体上之后转印于其他的支撑基体上,其应用方法并无限定。
另外,作为使本发明的光固化性组合物固化时所使用的活性光的光源,可以使用发出波长为300~450nm的光的光源,例如可以使用超高压汞、汞蒸汽弧、碳弧、氙弧等。
进而,通过在曝光光源中使用激光、在不使用掩模的情况下由计算机等的数字信息直接形成图像的激光直接描绘法由于不仅可谋求生产率的提高、而且还可谋求分辨率或位置精度等的提高,因此是有用的,作为其激光,优选使用340~430nm的波长的光,还可使用氩离子激光器、氦氖激光器、YAG激光器及半导体激光器等发出可见光~红外区域的光的装置。使用这些激光器时,可添加吸收可见~红外的该区域的增感色素。
本发明的光固化组合物可以用于涂料、涂布剂、内衬剂、油墨、抗蚀剂、液状抗蚀剂、粘着剂、印刷版、绝缘清漆、绝缘片、层叠板、印刷基板、半导体装置用/LED包装用/液晶注入口用/有机EL用/光元件用/电绝缘用/电子部件用/分离膜用等的密封剂、成形材料、油灰、玻璃纤维含浸剂、填充剂、半导体用/太阳能电池用等的钝化膜、层间绝缘膜、保护膜等中。
本发明的光固化性组合物使用黑色颜料作为着色剂时,可以以形成黑色矩阵的目的来使用,该黑色矩阵特别是对于液晶显示面板等图像显示装置用的显示设备用滤色器是有用的。
上述黑色矩阵更优选通过以下工序形成:(1)在基板上形成本发明的光固化性组合物的涂膜的工序、(2)隔着具有规定图案形状的掩模对该涂膜照射活性光的工序、(3)使用显影液(特别是碱显影液)对曝光后的覆膜进行显影的工序、(4)对显影后的该覆膜进行加热的工序。另外,本发明的光固化性组合物作为没有显影工序的喷墨方式的组合物也是有用的。
液晶显示面板等中使用的滤色器的制造可使用本发明或其他的光固化性组合物反复进行上述(1)~(4)的工序、组合2色以上的图案来制成。
实施例
以下举出实施例等更为详细地说明本发明,但本发明并不限定于这些实施例。
[制造例1]光聚合性不饱和化合物No.1的制备
装入1,1-双[4-(2,3-环氧丙氧基)苯基]茚满30.0g、丙烯酸7.52g、2,6-二叔丁基-对甲酚0.080g、四丁基氯化铵0.183g及PGMEA11.0g,在90℃下搅拌1小时、105℃下搅拌1小时及120℃下搅拌17小时。冷却至室温,添加琥珀酸酐8.11g、四丁基氯化铵0.427g及PGMEA11.1g,在100℃下搅拌5小时。然后,添加1,1-双[4-(2,3-环氧丙氧基)苯基]茚满12.0g、2,6-二叔丁基-对甲酚0.080g及PGMEA0.600g,在90℃下搅拌90分钟、120℃下搅拌5小时后,添加PGMEA24.0g,获得PGMEA溶液形式的光聚合性不饱和化合物No.1(Mw=4900、Mn=2250、酸值(固体成分)为47mg·KOH/g、固体成分为44.5质量%)。
[制造例2]光聚合性不饱和化合物No.2的制备
装入1,1-双[4-(2,3-环氧丙氧基)苯基]茚满184g、丙烯酸58g、2,6-二叔丁基-对甲酚0.26g、四正丁基溴化铵0.11g及PGMEA23g,在120℃下搅拌16小时。将反应液冷却至室温,添加PGMEA35g、联苯四甲酸二酐59g及四正丁基溴化铵0.24g,在120℃下搅拌4小时。然后,添加四氢邻苯二甲酸酐20g,在120℃下搅拌4小时、100℃下搅拌3小时、80℃下搅拌4小时、60℃下搅拌6小时、40℃下搅拌11小时后,添加PGMEA90g,获得PGMEA溶液形式的光聚合性不饱和化合物No.2(Mw=5000、Mn=2100、酸值(固体成分)为92.7mg·KOH/g、固体成分为44.4质量%)。
[制造例3]光聚合性不饱和化合物No.3的制备
装入1,1-双[4-(2,3-环氧丙氧基)苯基]茚满43g、丙烯酸11g、2,6-二叔丁基-对甲酚0.05g、四丁基乙酸铵0.11g及PGMEA23g,在120℃下搅拌16小时。冷却至室温,添加PGMEA35g及联苯四甲酸二酐9.4g,在120℃下搅拌8小时。然后,添加四氢邻苯二甲酸酐6.0g,在120℃下搅拌4小时、100℃下搅拌3小时、80℃下搅拌4小时、60℃下搅拌6小时、40℃下搅拌11小时后,添加PGMEA29g,获得PGMEA溶液形式的光聚合性不饱和化合物No.3(Mw=4000、Mn=2100、酸值(固体成分)为86mg·KOH/g、固体成分为44.5质量%),
[比较制造例1]比较光聚合性不饱和化合物No.1的制造
装入9,9-双(4-缩水甘油氧基苯基)芴75.0g、丙烯酸23.8g、2,6-二叔丁基-对甲酚0.273g、四丁基氯化铵0.585g及PGMEA65.9g,在90℃下搅拌1小时、100℃下搅拌1小时、110℃下搅拌1小时及120℃下搅拌14小时。冷却至室温,添加琥珀酸酐25.9g、四丁基氯化铵0.427g及PGMEA1.37g,在100℃下搅拌5小时。然后,添加9,9-双(4-缩水甘油氧基苯基)芴30.0g、2,6-二叔丁基-对甲酚0.269g及PGMEA1.50g,在90℃下搅拌90分钟、120℃下搅拌4小时后,添加PGMEA93.4g,获得PGMEA溶液形式的作为目标物的比较光聚合性不饱和化合物No.1(Mw=4190、Mn=2170、酸值(固体成分)为52mg·KOH/g、固体成分为55.0质量%)。
[实施例1~7及比较例1~2]光固化性组合物No.1~No.7及比较光固化性组合物No.1~No.2的制备
按照表1的配比获得光固化性组合物No.1~No.7及比较光固化性组合物No.1~No.2。其中,数字表示质量份。
表1
实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 实施例6 | 实施例7 | 比较例1 | 比较例2 | |
A-1 | 3.5 | 3.5 | 3.5 | 3.5 | |||||
A-2 | 3.5 | 3.5 | |||||||
A-3 | 3.5 | ||||||||
A’-1 | 3.5 | ||||||||
B-1 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | |||
B-2 | 0.5 | 0.5 | |||||||
C-1 | 0.8 | 0.8 | 0.8 | 0.8 | 0.8 | 0.8 | 0.8 | ||
C-2 | 0.8 | ||||||||
C-3 | 0.8 | ||||||||
D-1 | 8.6 | 8.6 | 8.6 | 8.6 | 8.6 | 8.6 | 8.6 | ||
D-2 | 8.6 | 8.6 | |||||||
E-1 | 1.1 | 1.1 | 1.1 | 1.1 | 1.1 | 1.1 | 1.1 | ||
E-2 | 1.1 | 1.1 | |||||||
E-3 | 75 | 75 | 75 | 75 | 75 | 75 | 75 | 75 | 75 |
感度 | a | a | a | a | b | a | b | a | c |
耐热性 | ○ | ○ | ○ | ○ | ○ | ○ | ○ | × | ○ |
A-1 光聚合性不饱和化合物No.1
A-2 光聚合性不饱和化合物No.2
A-3 光聚合性不饱和化合物No.3
A’-1 比较光聚合性不饱和化合物No.1
B-1 Karenz MT PE1 (昭和电工公司制)
B-2 Karenz MT BD1 (昭和电工公司制)
C-1 OXE-01 (BASF公司制)
C-2 OXE-02 (BASF公司制)
C-3 N-1919 (ADEKA公司制)
D-1 MA100 (炭黑;三菱化学公司制)
D-2 13M-C (钛黑;三菱Materials公司制)
E-1 Kayarad (多官能丙烯酸酯,日本化药公司制)
E-2 Aronix M-315 (多官能丙烯酸酯;东亚合成公司制)
E-3 PGMEA
[评价例1~7及比较评价例1~2]
将γ-环氧丙氧基丙基甲基乙氧基硅烷旋涂至基板上,使其旋转干燥后,将实施例1~7中获得的光固化性组合物No.1~No.7及比较例1~2中获得的比较光固化性组合物No.1~No.2旋涂(1300r.p.m、50秒)并干燥。在70℃下预烘焙20分钟后,涂布聚乙烯醇5%溶液,制成氧阻断膜。在70℃下干燥20分钟后,使用规定的掩模,使用超高压汞灯作为光源进行曝光后,在25℃下浸渍于2.5%碳酸钠溶液中30秒进行显影,并充分地水洗。水洗干燥后,在230℃下烘焙1小时,使图案固定。对所得的图案进行以下的感度、耐热性的评价。将结果示于表1。
[感度]
将曝光时曝光量为70mJ/cm2时即充分曝光的情况评价为a,将70mJ/cm2时曝光不充分、在100mJ/cm2时曝光了的情况评价为b,将100mJ/cm2时曝光不充分、在150mJ/cm2时曝光了的情况评价为c。
(耐热性试验)
将230℃下烘焙3小时、自初始的膜厚变化不足1%的情况评价为○,将上述膜厚变化为1%以上但不足5%的情况评价为△,将上述膜厚变化为5%以上的情况评价为×。
由以上的结果可知,含有具有特定结构的光聚合性不饱和化合物的本发明的光固化性组合物的感度及耐热性优异。因此,本发明的光固化性组合物对于滤色器是有用的。
Claims (6)
1.一种光固化性组合物,其含有具有下述结构的光聚合性不饱和化合物(A)、多官能硫醇化合物(B)、光聚合引发剂(C)及着色剂(D),所述结构为通过具有在下述通式(I)所示的环氧化合物上加成不饱和一元酸而成的结构的环氧加成化合物与多元酸酐的酯化反应获得的反应产物的结构,
式中,R1、R2、R3及R4各自独立地表示氢原子、碳原子数为1~5的烷基、碳原子数为1~8的烷氧基、碳原子数为2~5的链烯基或者卤原子;Y及Z各自独立地表示碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳基烷基、碳原子数为2~20的杂环基或者卤原子;所述烷基及芳基烷基中的亚烷基部分可以被不饱和键、-O-或-S-中断;Z还可以相邻Z之间形成环;m表示0~10的整数,p表示0~4的整数,q表示0~8的整数,r表示0~4的整数,s表示0~4的整数,r和s的数值之和为2~4的整数。
2.根据权利要求1所述的光固化性组合物,其特征在于,多官能硫醇化合物(B)由下述通式(II)表示,
式中,Q是碳原子数为1~10的亚烷基;n表示2~6的整数;X1表示具有与n相同价数的碳原子数为1~20的饱和烃基。
3.根据权利要求1所述的光固化性组合物,其特征在于,光聚合引发剂(C)由下述通式(III)表示,
式中,R6及R7各自独立地表示氢原子、氰基、碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳基烷基或碳原子数为2~20的杂环基;
R8及R9各自独立地表示氢原子、卤原子、硝基、氰基、羟基、羧基、R10、OR11、SR12、NR13R14、COR15、SOR16、SO2R17或CONR18R19,R8及R9还可相互键合形成环;
R10、R11、R12、R13、R14、R15、R16、R17、R18及R19各自独立地表示碳原子数为1~20的烷基、碳原子数为6~30的芳基、碳原子数为7~30的芳基烷基或碳原子数为2~20的杂环基;
X2表示氧原子、硫原子、硒原子、CR20R21、CO、NR22或PR23;
X3表示单键或CO;
R20、R21、R22及R23各自独立地表示氢原子、碳原子数为1~20的烷基、碳原子数为6~30的芳基或碳原子数为7~30的芳基烷基,所述烷基或芳基烷基中的亚甲基还可以被卤原子、硝基、氰基、羟基、羧基或杂环基取代,也可以被-O-中断;
R20、R21、R22及R23各自独立地可以与相邻的任一个苯环一起形成环;
a表示0~4的整数;
b表示0~5的整数。
4.根据权利要求1所述的光固化性组合物,其特征在于,所述着色剂(D)为黑色颜料。
5.一种黑色矩阵,其使用了权利要求4所述的光固化性组合物。
6.一种滤色器,其具有权利要求5所述的黑色矩阵。
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