JP6564253B2 - 化合物、及びそれを含むネガ型感光性組成物 - Google Patents
化合物、及びそれを含むネガ型感光性組成物 Download PDFInfo
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- JP6564253B2 JP6564253B2 JP2015120901A JP2015120901A JP6564253B2 JP 6564253 B2 JP6564253 B2 JP 6564253B2 JP 2015120901 A JP2015120901 A JP 2015120901A JP 2015120901 A JP2015120901 A JP 2015120901A JP 6564253 B2 JP6564253 B2 JP 6564253B2
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- photosensitive composition
- negative photosensitive
- bis
- acid
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- 239000000203 mixture Substances 0.000 title claims description 166
- 150000001875 compounds Chemical class 0.000 title claims description 96
- 229920005989 resin Polymers 0.000 claims description 79
- 239000011347 resin Substances 0.000 claims description 79
- 229920000647 polyepoxide Polymers 0.000 claims description 64
- 239000003822 epoxy resin Substances 0.000 claims description 63
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- 239000003960 organic solvent Substances 0.000 claims description 41
- 239000011248 coating agent Substances 0.000 claims description 29
- 238000000576 coating method Methods 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 29
- 229920001721 polyimide Polymers 0.000 claims description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 239000003086 colorant Substances 0.000 claims description 16
- 150000002460 imidazoles Chemical class 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229940125782 compound 2 Drugs 0.000 claims description 5
- 229940125904 compound 1 Drugs 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000009719 polyimide resin Substances 0.000 claims description 2
- -1 imidazole compound Chemical class 0.000 description 158
- 125000004432 carbon atom Chemical group C* 0.000 description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 45
- 125000000962 organic group Chemical group 0.000 description 44
- 239000002253 acid Substances 0.000 description 40
- 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 39
- 125000000217 alkyl group Chemical group 0.000 description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 35
- 125000005843 halogen group Chemical group 0.000 description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 31
- 239000004642 Polyimide Substances 0.000 description 27
- 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 27
- 239000002243 precursor Substances 0.000 description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 23
- 239000000049 pigment Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 21
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 19
- 229920003986 novolac Polymers 0.000 description 19
- 125000003700 epoxy group Chemical group 0.000 description 18
- 239000003999 initiator Substances 0.000 description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 17
- 239000004593 Epoxy Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000004429 atom Chemical group 0.000 description 15
- 230000002349 favourable effect Effects 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 14
- 125000002723 alicyclic group Chemical group 0.000 description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 14
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 14
- 125000005372 silanol group Chemical group 0.000 description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 14
- 125000000101 thioether group Chemical group 0.000 description 14
- 125000003396 thiol group Chemical group [H]S* 0.000 description 14
- 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 13
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 13
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 13
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000004985 diamines Chemical class 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 11
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 11
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000006229 carbon black Substances 0.000 description 10
- 235000019241 carbon black Nutrition 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 238000000059 patterning Methods 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 229920005575 poly(amic acid) Polymers 0.000 description 8
- 239000001294 propane Substances 0.000 description 8
- 229930185605 Bisphenol Natural products 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 125000003368 amide group Chemical group 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229960003742 phenol Drugs 0.000 description 7
- 150000007519 polyprotic acids Polymers 0.000 description 7
- 229940079877 pyrogallol Drugs 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine powder Natural products NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
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- 239000002904 solvent Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- 125000002252 acyl group Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 125000004427 diamine group Chemical group 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
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- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
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- 125000000524 functional group Chemical group 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 4
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- 125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 description 4
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- 238000000746 purification Methods 0.000 description 4
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 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
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- XOPKKHCDIAYUSK-UHFFFAOYSA-N 2-[2-(5-methylfuran-2-yl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound O1C(C)=CC=C1C=CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 XOPKKHCDIAYUSK-UHFFFAOYSA-N 0.000 description 3
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
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- 239000003377 acid catalyst Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
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- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
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- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- VRAWXSCCKYEDOG-UHFFFAOYSA-N tribenzylsulfanium Chemical compound C=1C=CC=CC=1C[S+](CC=1C=CC=CC=1)CC1=CC=CC=C1 VRAWXSCCKYEDOG-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- DMJFWVWYOPMJIK-UHFFFAOYSA-N tris[3,4-bis[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound C1=C(OC(C)(C)C)C(OC(C)(C)C)=CC=C1[S+](C=1C=C(OC(C)(C)C)C(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C(OC(C)(C)C)=C1 DMJFWVWYOPMJIK-UHFFFAOYSA-N 0.000 description 1
- HENPLGIMUIZOJQ-UHFFFAOYSA-N tris[3-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound CC(C)(C)OC1=CC=CC([S+](C=2C=C(OC(C)(C)C)C=CC=2)C=2C=C(OC(C)(C)C)C=CC=2)=C1 HENPLGIMUIZOJQ-UHFFFAOYSA-N 0.000 description 1
- YNIMTIPTLNZOMC-UHFFFAOYSA-N tris[4-(dimethylamino)phenyl]sulfanium Chemical compound C1=CC(N(C)C)=CC=C1[S+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 YNIMTIPTLNZOMC-UHFFFAOYSA-N 0.000 description 1
- PNXQORBBJALXKA-UHFFFAOYSA-N tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 PNXQORBBJALXKA-UHFFFAOYSA-N 0.000 description 1
- JXPBRQHHMIKAPW-UHFFFAOYSA-N tris[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]sulfanium Chemical compound C1=CC(OCC(=O)OC(C)(C)C)=CC=C1[S+](C=1C=CC(OCC(=O)OC(C)(C)C)=CC=1)C1=CC=C(OCC(=O)OC(C)(C)C)C=C1 JXPBRQHHMIKAPW-UHFFFAOYSA-N 0.000 description 1
- KQAYXXFFBQKDEP-UHFFFAOYSA-N undecane-6,6-diamine Chemical compound CCCCCC(N)(N)CCCCC KQAYXXFFBQKDEP-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 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
- 239000004246 zinc acetate Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- Liquid Crystal (AREA)
- Materials For Photolithography (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Optical Filters (AREA)
Description
しかし、特許文献1のように密着増強剤としてアミン系シランカップリング剤を含有させた場合には、基板との密着性は向上するものの、良好に硬化したパターンを形成するための時間については短縮化が望まれるものである。
R4及びR5は、それぞれ独立に水素原子、ハロゲン原子、水酸基、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、又は有機基を示し、
Arは、下記式(2)〜(4):
式(2)中、X1は=CR6−又は=N−を示し、X2は=CR7−又は=N−を示し、X3は=CR8−又は=N−を示し、X4は=CR9−又は=N−を示し、X5は=CR10−又は=N−を示し、
X1、X2、X3、X4、及びX5は、同時に=CH−ではなく、
R6及びR7は、それぞれ独立に水素原子、ハロゲン原子、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、アミノ基、アンモニオ基、又は有機基を示し、
R8及びR9は、それぞれ独立に水素原子、ハロゲン原子、水酸基、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、アミノ基、アンモニオ基、又は有機基を示し、
R10は、水素原子、ハロゲン原子、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、アミノ基、アンモニオ基、又は式(2)で示される環に炭素−炭素結合を介して結合する有機基を示し、
式(2)で示される環上にR6〜R10のうちの2つの基が隣接して存在する場合、隣接する2つの基は縮合して環を形成してもよく、
式(3)及び式(4)中、X6は=CR11−又は=N−を示し、X7は=CR12−又は=N−を示し、X8は=CR13−又は=N−を示し、X9は−O−、−S−、又は−NH−を示し、X10は=CR14−又は=N−を示し、X11は=CR15−又は=N−を示し、X12は=CR16−又は=N−を示し、X13は−O−、−S−、又は−NH−を示し、
R11、R12、R13、R14、R15、及びR16は、それぞれ独立に水素原子、ハロゲン原子、水酸基、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、アミノ基、アンモニオ基、又は有機基を示し、
式(3)又は式(4)で示される環上に、R11〜R13のうちの2つの基が隣接して存在するか、R14〜R16のうちの2つの基が隣接して存在する場合、隣接する2つの基は縮合して環を形成してもよく、
Arが式(3)で示される基であり、X9が−S−である場合に、X8は=CCH3−ではない。)
本発明に係る化合物は、下記式(1)で表されるものである。
R4及びR5は、それぞれ独立に水素原子、ハロゲン原子、水酸基、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、又は有機基を示し、
Arは、下記式(2)〜(4):
式(2)中、X1は=CR6−又は=N−を示し、X2は=CR7−又は=N−を示し、X3は=CR8−又は=N−を示し、X4は=CR9−又は=N−を示し、X5は=CR10−又は=N−を示し、
X1、X2、X3、X4、及びX5は、同時に=CH−ではなく、
R6及びR7は、それぞれ独立に水素原子、ハロゲン原子、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、アミノ基、アンモニオ基、又は有機基を示し、
R8及びR9は、それぞれ独立に水素原子、ハロゲン原子、水酸基、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、アミノ基、アンモニオ基、又は有機基を示し、
R10は、水素原子、ハロゲン原子、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、アミノ基、アンモニオ基、又は式(2)で示される環に炭素−炭素結合を介して結合する有機基を示し、
式(2)で示される環上にR6〜R10のうちの2つの基が隣接して存在する場合、隣接する2つの基は縮合して環を形成してもよく、
式(3)及び式(4)中、X6は=CR11−又は=N−を示し、X7は=CR12−又は=N−を示し、X8は=CR13−又は=N−を示し、X9は−O−、−S−、又は−NH−を示し、X10は=CR14−又は=N−を示し、X11は=CR15−又は=N−を示し、X12は=CR16−又は=N−を示し、X13は−O−、−S−、又は−NH−を示し、
R11、R12、R13、R14、R15、及びR16は、それぞれ独立に水素原子、ハロゲン原子、水酸基、メルカプト基、スルフィド基、シリル基、シラノール基、ニトロ基、ニトロソ基、スルフィノ基、スルホ基、スルホナト基、ホスフィノ基、ホスフィニル基、ホスホノ基、ホスホナト基、アミノ基、アンモニオ基、又は有機基を示し、
式(3)又は式(4)で示される環上に、R11〜R13のうちの2つの基が隣接して存在するか、R14〜R16のうちの2つの基が隣接して存在する場合、隣接する2つの基は縮合して環を形成してもよく、
Arが式(3)で示される基であり、X9が−S−である場合に、X8は=CCH3−ではない。)
本発明に係るネガ型感光性組成物としては、従来公知のネガ型感光性組成物に上記式(1)で表される化合物を添加したものを、特に制限されずに用いることができる。以下、本発明に係るネガ型感光性組成物の具体例について詳細に説明する。
なお、以下の具体例に限定されるものではないが、ネガ型感光性組成物は、上記式(1)で表される化合物、アルカリ可溶性樹脂、光重合開始剤、及び有機溶剤を有することが好ましい。必要に応じて光重合性モノマーを用いてもよい。
アルカリ可溶性樹脂としては、カルド構造を有する樹脂、フェノール性水酸基を有する樹脂、ポリイミド樹脂、及びエポキシ樹脂よりなる群から選択される樹脂を含有することが好ましい。光重合開始剤、有機溶剤、光重合性モノマーの詳細についても、後述する第1〜7の態様のネガ型感光性組成物において説明する。
第1の態様のネガ型感光性組成物は、光重合性モノマーと、上記式(1)で表される化合物とを含有する。第1の態様のネガ型感光性組成物は、必要に応じて、光重合開始剤、及び有機溶剤等を含んでいてもよい。
第2の態様のネガ型感光性組成物は、アルカリ可溶性樹脂、光重合性モノマー、光重合開始剤、上記式(1)で表される化合物、及び有機溶剤を含有する。
なお、本明細書においてアルカリ可溶性樹脂とは、樹脂濃度20質量%の樹脂溶液(溶媒:プロピレングリコールモノメチルエーテルアセテート)により、膜厚1μmの樹脂膜を基板上に形成し、2.38質量%のテトラメチルアンモニウムヒドロキシド(TMAH)水溶液に1分間浸漬した際に、膜厚0.01μm以上溶解するものをいう。
また、上記式(a−1)中、mは、0〜20の整数を示す。
C.I.ピグメントオレンジ1(以下、「C.I.ピグメントオレンジ」は同様であり、番号のみを記載する。)、5、13、14、16、17、24、34、36、38、40、43、46、49、51、55、59、61、63、64、71、73;
C.I.ピグメントバイオレット1(以下、「C.I.ピグメントバイオレット」は同様であり、番号のみを記載する。)、19、23、29、30、32、36、37、38、39、40、50;
C.I.ピグメントレッド1(以下、「C.I.ピグメントレッド」は同様であり、番号のみを記載する。)、2、3、4、5、6、7、8、9、10、11、12、14、15、16、17、18、19、21、22、23、30、31、32、37、38、40、41、42、48:1、48:2、48:3、48:4、49:1、49:2、50:1、52:1、53:1、57、57:1、57:2、58:2、58:4、60:1、63:1、63:2、64:1、81:1、83、88、90:1、97、101、102、104、105、106、108、112、113、114、122、123、144、146、149、150、151、155、166、168、170、171、172、174、175、176、177、178、179、180、185、187、188、190、192、193、194、202、206、207、208、209、215、216、217、220、223、224、226、227、228、240、242、243、245、254、255、264、265;
C.I.ピグメントブルー1(以下、「C.I.ピグメントブルー」は同様であり、番号のみを記載する。)、2、15、15:3、15:4、15:6、16、22、60、64、66;
C.I.ピグメントグリーン7、C.I.ピグメントグリーン36、C.I.ピグメントグリーン37;
C.I.ピグメントブラウン23、C.I.ピグメントブラウン25、C.I.ピグメントブラウン26、C.I.ピグメントブラウン28;
C.I.ピグメントブラック1、C.I.ピグメントブラック7。
特に、第2の態様のネガ型感光性組成物を使用してブラックマトリクスを形成する場合には、ブラックマトリクスの膜厚1μm当たりのOD値が4以上となるように、ネガ型感光性組成物における遮光剤の量を調整することが好ましい。ブラックマトリクスにおける膜厚1μm当たりのOD値が4以上あれば、液晶表示ディスプレイのブラックマトリクスに用いた場合に、十分な表示コントラストを得ることができる。
この場合、さらに光重合開始剤を含有すると、上記式(1)で表される化合物からの置換又は無置換のイミダゾールの発生が促進されるため好ましい。すなわち、電磁波照射によって光重合開始剤からラジカルが発生すると、このラジカルによって上記式(1)で表される化合物が攻撃され、置換又は無置換のイミダゾールの発生が促進される。また、上記式(1)で表される化合物から発生した置換又は無置換のイミダゾールがラジカルを補足することにより、置換又は無置換のイミダゾールの発生反応の平衡が移動し、さらに置換又は無置換のイミダゾールを発生するようになる。さらに、上記式(1)で表される化合物から発生した置換又は無置換のイミダゾールとラジカル発生後の化合物とが反応し、置換又は無置換のイミダゾールの発生がさらに促進される。
第3の態様のネガ型感光性組成物は、フェノール性水酸基を有するアルカリ可溶性樹脂、酸架橋性物質、光酸発生剤、上記式(1)で表される化合物、及び有機溶剤を含有する。
ポリヒドロキシスチレン系樹脂は、ヒドロキシスチレンに由来する構成単位を少なくとも有する。
ここで「ヒドロキシスチレン」とは、ヒドロキシスチレン、及びヒドロキシスチレンのα位に結合する水素原子がハロゲン原子、アルキル基、ハロゲン化アルキル基等の他の置換基に置換されたもの、並びにそれらの誘導体のヒドロキシスチレン誘導体(モノマー)を含む概念とする。
「ヒドロキシスチレン誘導体」は、少なくともベンゼン環とこれに結合する水酸基とが維持されており、例えば、ヒドロキシスチレンのα位に結合する水素原子が、ハロゲン原子、炭素数1〜5のアルキル基、ハロゲン化アルキル基等の他の置換基に置換されたもの、並びにヒドロキシスチレンの水酸基が結合したベンゼン環に、さらに炭素数1〜5のアルキル基が結合したものや、この水酸基が結合したベンゼン環に、さらに1〜2個の水酸基が結合したもの(このとき、水酸基の数の合計は2〜3である。)等を包含するものとする。
ハロゲン原子としては、塩素原子、フッ素原子、臭素原子等が挙げられ、フッ素原子が好ましい。
なお、「ヒドロキシスチレンのα位」とは、特に断りがない限り、ベンゼン環が結合している炭素原子のことをいう。
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられ、フッ素原子が好ましい。
ハロゲン化アルキル基としては、上述した炭素数1〜5のアルキル基の水素原子の一部又は全部がハロゲン原子で置換されたものである。この中でも、水素原子の全部がフッ素原子で置換されたものが好ましい。また、直鎖状又は分岐鎖状のフッ素化アルキル基が好ましく、トリフルオロメチル基、ヘキサフルオロエチル基、ヘプタフルオロプロピル基、ノナフルオロブチル基等がより好ましく、トリフルオロメチル基(−CF3)が最も好ましい。
Rb1としては、水素原子又はメチル基が好ましく、水素原子がより好ましい。
qは0〜2の整数である。これらの中でも0又は1であることが好ましく、工業上は特に0であることが好ましい。
Rb2の置換位置は、qが1である場合にはオルト位、メタ位、パラ位のいずれでもよく、さらに、qが2の場合には任意の置換位置を組み合わせることができる。
pは1〜3の整数であり、好ましくは1である。
水酸基の置換位置は、pが1である場合にはオルト位、メタ位、パラ位のいずれでもよいが、容易に入手可能で低価格であることからパラ位が好ましい。さらに、pが2又は3の場合には任意の置換位置を組み合わせることができる。
ここで「スチレンに由来する構成単位」とは、スチレン及びスチレン誘導体(但し、ヒドロキシスチレンは含まない。)のエチレン性二重結合が開裂してなる構成単位を包含するものとする。
「スチレン誘導体」は、スチレンのα位に結合する水素原子が、ハロゲン原子、アルキル基、ハロゲン化アルキル基等の他の置換基に置換されたもの、並びにスチレンのフェニル基の水素原子が、炭素数1〜5のアルキル基等の置換基に置換されているもの等を包含するものとする。
ハロゲン原子としては、塩素原子、フッ素原子、臭素原子等が挙げられ、フッ素原子が好ましい。
なお、「スチレンのα位」とは、特に断りがない限り、ベンゼン環が結合している炭素原子のことをいう。
qは0〜2の整数である。これらの中でも0又は1であることが好ましく、工業上は特に0であることが好ましい。
Rb2の置換位置は、qが1である場合にはオルト位、メタ位、パラ位のいずれでもよく、さらに、qが2の場合には任意の置換位置を組み合わせることができる。
これらのフェノール類の中でも、m−クレゾール、p−クレゾールが好ましく、m−クレゾールとp−クレゾールとを併用することがより好ましい。この場合、両者の配合割合を調整することにより、感度等の諸特性を調整することができる。
これらの酸架橋性物質は、単独又は2種以上組み合わせて用いることができる。
また、上記以外にも、下記式(c−3)で表される化合物が挙げられる。
Rc5としては芳香族性化合物基であることが特に好ましく、このような芳香族性化合物基としては、フェニル基、ナフチル基等の芳香族炭化水素基や、フリル基、チエニル基等の複素環基等が挙げられる。これらは環上に適当な置換基、例えばハロゲン原子、アルキル基、アルコキシ基、ニトロ基等を1個以上有していてもよい。また、Rc6としては炭素数1〜6のアルキル基が特に好ましく、メチル基、エチル基、プロピル基、ブチル基が挙げられる。また、rは1〜3の整数が好ましく、1又は2がより好ましい。
これらの光酸発生剤は、単独又は2種以上組み合わせて用いることができる。
これらの化合物は、単独又は2種以上組み合わせて用いることができる。
有機溶剤の含有量は、第3の態様のネガ型感光性組成物の固形分濃度が1〜50質量%となる量が好ましく、5〜30質量%となる量がより好ましい。
第4の態様のネガ型感光性組成物は、感光性ポリイミド前駆体、光重合性モノマー、光重合開始剤、上記式(1)で表される化合物、及び有機溶剤を含有する。
この脂肪族ジアミンを用いる場合、その配合量は、全ジアミンのうち20モル%以下であることが、現像時の膨潤が少なく、また形成される膜の耐熱性等の点から好ましい。
光重合性モノマーの含有量は、感光性ポリイミド前駆体100質量部に対して5〜100質量部であることが好ましく、5〜40質量部であることがより好ましい。上記の範囲とすることにより、感度、現像性、解像性のバランスがとりやすい傾向がある。
光重合開始剤の含有量は、感光性ポリイミド前駆体100質量部に対して0.01〜40質量部であることが好ましい。上記の範囲とすることにより、十分な耐熱性、耐薬品性を得ることができ、また塗膜形成能を向上させ、硬化不良を抑制することができる。
有機溶剤の含有量は、第4の態様のネガ型感光性組成物の固形分濃度が1〜50質量%となる量が好ましく、5〜30質量%となる量がより好ましい。
第5の態様のネガ型感光性組成物は、ポリイミド前駆体、上記式(1)で表される化合物、及び有機溶剤を含有する。
ポリイミド前駆体としては、Re3及びRe4が水素原子であるようなポリアミック酸が、アルカリ現像性の点から好適に用いられる。
これらの酸二無水物は、単独又は2種以上組み合わせて用いることができる。
これらのジアミンは、単独又は2種以上組み合わせて用いることができる。
有機溶剤の含有量は、第5の態様のネガ型感光性組成物の固形分濃度が1〜50質量%となる量が好ましく、5〜30質量%となる量がより好ましい。
第6の態様のネガ型感光性組成物は、エポキシ樹脂、上記式(1)で表される化合物、及び有機溶剤を含有する。
市販されているエポキシ樹脂製品としては、例えばジャパンエポキシレジン社製のJERコート828、1001、801N、806、807、152、604、630、871、YX8000、YX8034、YX4000、DIC社製のエピクロン830、EXA835LV、HP4032D、HP820、株式会社ADEKA製のEP4100シリーズ、EP4000シリーズ、EPUシリーズ、ダイセル社製のセロキサイドシリーズ(2021、2021P、2083、2085、3000等)、エポリードシリーズ、EHPEシリーズ、新日鐵化学社製のYDシリーズ、YDFシリーズ、YDCNシリーズ、YDBシリーズ、フェノキシ樹脂(ビスフェノール類とエピクロルヒドリンより合成されるポリヒドロキシポリエーテルで両末端にエポキシ基を有する;YPシリーズ等)、ナガセケムテックス社製のデナコールシリーズ、共栄社化学社製のエポライトシリーズ等が挙げられるがこれらに限定されるものではない。
これらのエポキシ樹脂は、単独又は2種以上組み合わせて用いることができる。
有機溶剤の含有量は、第6の態様のネガ型感光性組成物の固形分濃度が1〜50質量%となる量が好ましく、5〜30質量%となる量がより好ましい。
第7の態様のネガ型感光性組成物は、エポキシ基含有ポリカルボン酸樹脂、光酸発生剤、上記式(1)で表される化合物、及び有機溶剤を含有する。
光酸発生剤の含有量は、第7の態様のネガ型感光性組成物の固形分に対して0.5〜30質量%であることが好ましく、1〜20質量%であることがより好ましい。上記の範囲とすることにより、ネガ型感光性組成物の硬化性が良好になる。
充填剤の含有量は、第7の態様のネガ型感光性組成物の固形分に対して60質量%以下であることが好ましく、5〜40質量%であることがより好ましい。
有機溶剤の含有量は、第7の態様のネガ型感光性組成物の固形分濃度が1〜50質量%となる量が好ましく、5〜30質量%となる量がより好ましい。
本発明に係るネガ型感光性組成物は、上記の各成分を撹拌機で混合することにより調製される。なお、調製されたネガ型感光性組成物が均一なものとなるよう、メンブランフィルタ等を用いて濾過してもよい。
本発明に係るパターン形成方法は、本発明に係るネガ型感光性組成物を用いて塗膜又は成形体を形成し、該塗膜又は成形体に対して所定パターン状に電磁波を照射し、現像するものである。
本発明に係る硬化膜、絶縁膜、及びカラーフィルタは、本発明に係るネガ型感光性組成物を用いて形成されたものである。
例えば、着色剤を含有しないネガ型感光性組成物を用いて塗膜を形成し、該塗膜に対して電磁波を照射及び/又は加熱することにより、透明な硬化膜や絶縁膜を得ることができる。このような硬化膜、絶縁膜は、例えば液晶表示ディスプレイや有機ELディスプレイ等の平坦化膜として、あるいは層間絶縁膜として用いられる。
なお、この硬化膜、絶縁膜は、パターン化されたものであってもよい。上記のように、塗膜に対して所定パターン状に電磁波を照射し、現像することにより、パターン化された硬化膜、絶縁膜を得ることができる。パターン化された硬化膜は、例えば液晶表示ディスプレイや有機ELディスプレイ等のスペーサ、隔壁として用いられる。
また、着色剤を含有するネガ型感光性組成物(特に第2の態様のネガ型感光性組成物)を用いて塗膜を形成し、該塗膜に対して所定パターン状に電磁波を照射し、現像することにより、例えば液晶表示ディスプレイのカラーフィルタの画素やブラックマトリクスを形成することもできる。
本発明に係る表示装置は、このような硬化膜、絶縁膜、カラーフィルタを備えるものである。表示装置としては、液晶表示ディスプレイや有機ELディスプレイ等が挙げられる。
3−(チオフェン−2−イル)アクリル酸クロリド5.17g(30mmol)を50mLの乾燥したエーテルに溶解し、トリエチルアミン4.59mL(当量比1.1)、イミダゾール2.25ml(当量比1.1)を加え、室温にて1時間撹拌した。水50mL、飽和NaHCO3水溶液50mL、及び1N塩酸で洗浄後、硫酸マグネシウムで乾燥し、減圧下で濃縮した。ヘキサン−酢酸エチルを展開溶媒とし、シリカゲルを支持担体としてカラムクロマトグラフィにより精製を行い、対応する化合物1を得た。
化合物1の1H−NMRの測定結果は以下のとおりである。
1H−NMR(CDCl3):6.824(d,1H,J=15.6Hz),7.127(dd,1H,J=2.7Hz,2.1Hz),7.145(dd,1H,J=0.9Hz,0.6Hz),7.428(d,1H,J=3.6Hz),7.514(d,1H,J=5.4Hz),7.593(dd,1H,J=1.5J,1.5J),8.159(d,1H,J=15Hz),8.279(s,1H)
4−ニトロ桂皮酸クロリド6.35g(30mmol)を50mLの乾燥したエーテルに溶解し、トリエチルアミン4.59mL(当量比1.1)、イミダゾール2.25mL(当量比1.1)を加え、室温にて1時間撹拌した。水50mL、飽和NaHCO3水溶液50mL、及び1N塩酸で洗浄後、硫酸マグネシウムで乾燥し、減圧下で濃縮した。ヘキサン−酢酸エチルを展開溶媒とし、シリカゲルを支持担体としてカラムクロマトグラフィにより精製を行い、対応する化合物2を得た。
化合物2の1H−NMRの測定結果は以下のとおりである。
1H−NMR(CDCl3):6.482(dd,1H,J=0.7Hz,0.4Hz),7.192(d,1H,15.1Hz),7.331(d,1H,15.1Hz),7.471(d,1H,J=8.6Hz),7.471(dd,1H,J=4.7Hz,2.1Hz),7.591(d,1H,8.6Hz),7.592(dd,1H,J=4.6Hz),7.652(dd,1H,J=1.4Hz),8.191(s,1H)
4−アミノ桂皮酸クロリド6.35g(30mmol)を50mLの乾燥したエーテルに溶解し、トリエチルアミン4.59mL(当量比1.1)、イミダゾール2.25mL(当量比1.1)を加え、室温にて1時間撹拌した。水50mL、飽和NaHCO3水溶液50mL、及び1N塩酸で洗浄後、硫酸マグネシウムで乾燥し、減圧下で濃縮した。ヘキサン−酢酸エチルを展開溶媒とし、シリカゲルを支持担体としてカラムクロマトグラフィにより精製を行い、対応する化合物Aを得た。
化合物Aの1H−NMRの測定結果は以下のとおりである。
1H−NMR(CDCl3):6.042(s,2H),6.637(d,1H,J=8.6Hz),6.637(dd,1H,J=4.7Hz,2.1Hz),7.110(dd,1H,J=0.7Hz,0.4Hz),7.252(d,1H,15.1Hz),7.631(d,1H,8.6Hz),7.631(dd,1H,J=4.6Hz),7.866(d,1H,15.1Hz),7.887(dd,1H,J=1.4Hz),8.653(s,1H)
3−(フラン−2−イル)アクリル酸クロリド5.17g(30mmol)を50mLの乾燥したエーテルに溶解し、トリエチルアミン4.59mL(当量比1.1)、イミダゾール2.25ml(当量比1.1)を加え、室温にて1時間撹拌した。水50mL、飽和NaHCO3水溶液50mL、及び1N塩酸で洗浄後、硫酸マグネシウムで乾燥し、減圧下で濃縮した。ヘキサン−酢酸エチルを展開溶媒とし、シリカゲルを支持担体としてカラムクロマトグラフィにより精製を行い、対応する化合物Bを得た。
化合物Bの1H−NMRの測定結果は以下のとおりである。
1H−NMR(CDCl3):6.441(dd,1H,J=2.7Hz,2.1Hz),6.651(d,1H,J=3.6Hz),6.701(d,1H,J=15.6Hz),7.191(dd,1H,J=0.9Hz,0.6Hz),7.33(d,1H,J=5.4Hz),7.421(d,1H,J=15Hz),7.533(dd,1H,J=1.5J,1.5J),8.19(s,1H)
トリメチロールプロパントリ(メタ)アクリレート(東京化成工業株式会社)62質量部、及びアクリル酸(和光純薬株式会社製、特級)38質量部からなる重合性化合物100質量部に対して、表1に記載の種類の式(1)で表される化合物又は式(1)で表される化合物に相当する比較化合物1質量部と、助剤を0又は1質量部と、水素供与体である4−ジメチルアミノ安息香酸エチル(和光純薬株式会社製、1級)1質量部を加えた後、均一に混合して、ネガ型感光性組成物を調製した。
得られたネガ型感光性組成物を、ポリエステルフィルム(東レ株式会社製、ルミラー(登録商標))の上に、ロッド(NO.8)を用いて塗布して、膜厚12μmの塗布膜を形成した。次いで、窒素雰囲気下(酸素濃度5000ppm)で、塗布膜の表面から2cmの距離から、出力80000mWの高圧水銀ランプ(中心波長365nm)を光源として用いて塗布膜を露光した。
Claims (13)
- さらに、光重合性化合物を含有する請求項2記載のネガ型感光性組成物。
- さらに、カルド構造を有する樹脂、フェノール性水酸基を有する樹脂、ポリイミド樹脂、及びエポキシ樹脂よりなる群から選択される樹脂を含有する請求項2記載のネガ型感光性組成物。
- さらに、アルカリ可溶性樹脂、光重合開始剤、及び有機溶剤を含有する請求項2記載のネガ型感光性組成物。
- さらに、光重合性モノマーを含有する請求項4記載のネガ型感光性組成物。
- さらに着色剤を含有する請求項5又は6記載のネガ型感光性組成物。
- 前記着色剤が遮光剤である請求項7記載のネガ型感光性組成物。
- 請求項2から8のいずれか1項記載のネガ型感光性組成物を用いて塗膜又は成形体を形成し、該塗膜又は成形体に対して所定パターン状に電磁波を照射し、現像するパターン形成方法。
- 請求項2から6のいずれか1項記載のネガ型感光性組成物を用いて形成された硬化膜。
- 請求項2から6のいずれか1項記載のネガ型感光性組成物を用いて形成された絶縁膜。
- 請求項7又は8記載のネガ型感光性組成物を用いて形成されたカラーフィルタ。
- 請求項10記載の硬化膜、請求項11記載の絶縁膜、又は請求項12記載のカラーフィルタを備える表示装置。
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