JP5744528B2 - Colored photosensitive resin composition for touch panel, touch panel, and display device - Google Patents
Colored photosensitive resin composition for touch panel, touch panel, and display device Download PDFInfo
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- JP5744528B2 JP5744528B2 JP2011003136A JP2011003136A JP5744528B2 JP 5744528 B2 JP5744528 B2 JP 5744528B2 JP 2011003136 A JP2011003136 A JP 2011003136A JP 2011003136 A JP2011003136 A JP 2011003136A JP 5744528 B2 JP5744528 B2 JP 5744528B2
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- meth
- touch panel
- compound
- photosensitive resin
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- 239000011342 resin composition Substances 0.000 title claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 76
- 239000004593 Epoxy Substances 0.000 claims description 47
- 229920005989 resin Polymers 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 32
- 239000011230 binding agent Substances 0.000 claims description 29
- 239000000049 pigment Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 13
- 239000003086 colorant Substances 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004018 acid anhydride group Chemical group 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- 238000004040 coloring Methods 0.000 claims description 4
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 60
- -1 aliphatic alcohols Chemical class 0.000 description 49
- 125000000623 heterocyclic group Chemical group 0.000 description 25
- 239000000126 substance Substances 0.000 description 25
- 238000012360 testing method Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000004020 conductor Substances 0.000 description 10
- 239000003822 epoxy resin Substances 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 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 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 125000000962 organic group Chemical group 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 229940059574 pentaerithrityl Drugs 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- 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 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 235000019241 carbon black Nutrition 0.000 description 5
- 229930003836 cresol Natural products 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
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- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- 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 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
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- 206010040844 Skin exfoliation Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
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- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
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- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- YSGBMDFJWFIEDF-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbutanoate Chemical compound COC(=O)C(O)C(C)C YSGBMDFJWFIEDF-UHFFFAOYSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229940074369 monoethyl fumarate Drugs 0.000 description 1
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 description 1
- 229940005650 monomethyl fumarate Drugs 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WXNYILVTTOXAFR-UHFFFAOYSA-N prop-2-en-1-ol;styrene Chemical compound OCC=C.C=CC1=CC=CC=C1 WXNYILVTTOXAFR-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- 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
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133512—Light shielding layers, e.g. black matrix
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Photolithography (AREA)
- Epoxy Resins (AREA)
- Position Input By Displaying (AREA)
- Optical Filters (AREA)
Description
本発明は、タッチパネル用着色感光性樹脂組成物、タッチパネル、及び表示装置に関する。 The present invention relates to a colored photosensitive resin composition for a touch panel, a touch panel, and a display device.
現在、液晶ディスプレイ等を有する表示装置における入力手段として、タッチパネルが広く用いられている。その中でも、光学的に明るいこと、構造が容易であること等の理由から、静電容量方式のタッチパネルが注目されている。 Currently, touch panels are widely used as input means in display devices having a liquid crystal display or the like. Among them, a capacitive touch panel is attracting attention because it is optically bright and has a simple structure.
静電容量方式のタッチパネルは、誘電体と、誘電体の両側に異なるパターンでそれぞれ形成された第1の導電体及び第2の導電体と、を有している。この第1の導電体及び第2の導電体は、アクティブエリア外の領域に形成された取出配線を介して外部の制御回路に接続される。このような静電容量方式のタッチパネルによれば、外部導体(典型的には、指)がタッチパネルに接触又は接近した際に生じる電磁的な変化又は静電容量の変化に基づき、外部導体の位置を検出することができる。 The capacitive touch panel has a dielectric, and a first conductor and a second conductor formed in different patterns on both sides of the dielectric, respectively. The first conductor and the second conductor are connected to an external control circuit via a lead-out wiring formed in a region outside the active area. According to such a capacitive touch panel, the position of the external conductor is based on an electromagnetic change or a change in capacitance that occurs when an external conductor (typically a finger) comes into contact with or approaches the touch panel. Can be detected.
ところで、このタッチパネルにおいては、第1の導電体及び第2の導電体として金属を使用可能とするため、第1の導電体及び第2の導電体をブラックマトリクスの後ろに隠すことが提案されている(特許文献1参照)。また、使用者側から視認できないように、取出配線をブラックマトリクスの後ろに隠すことも検討されている。このような場合、ブラックマトリクスを形成した後に金属膜をエッチング等することが必要であるため、ブラックマトリクスの材料としては耐薬品性が重要となる。
また、タッチパネルを備えた表示装置をカーナビゲーションシステムのような車載用途で使用する場合、ブラックマトリクスの材料としては耐候性が重要となる。
By the way, in this touch panel, in order to be able to use metal as the first conductor and the second conductor, it has been proposed to hide the first conductor and the second conductor behind the black matrix. (See Patent Document 1). It is also under consideration to hide the extraction wiring behind the black matrix so that it cannot be seen from the user side. In such a case, since it is necessary to etch the metal film after forming the black matrix, chemical resistance is important as a material for the black matrix.
Further, when a display device provided with a touch panel is used in an in-vehicle application such as a car navigation system, weather resistance is important as a black matrix material.
しかし、カラーフィルタのブラックマトリクス用の着色感光性樹脂組成物をタッチパネル用途に転用した場合、耐薬品性や耐候性の点で要求水準を満たさないという問題があった。 However, when the colored photosensitive resin composition for the black matrix of the color filter is diverted to a touch panel application, there is a problem that the required level is not satisfied in terms of chemical resistance and weather resistance.
本発明は、上記課題に鑑みてなされたものであり、耐薬品性、耐候性に優れ、タッチパネル用途に好適に用いられるタッチパネル用着色感光性樹脂組成物、そのタッチパネル用着色感光性樹脂組成物を用いて形成された硬化樹脂パターンを有するタッチパネル、及びそのタッチパネルを備えた表示装置を提供することを目的とする。 This invention is made | formed in view of the said subject, It is excellent in chemical-resistance and a weather resistance, The coloring photosensitive resin composition for touchscreens used suitably for a touchscreen use, The coloring photosensitive resin composition for touchscreens It aims at providing the touchscreen which has the cured resin pattern formed using, and a display apparatus provided with the touchscreen.
本発明者らは、上記目的を達成するため鋭意研究を重ねた。その結果、着色感光性樹脂組成物のバインダー化合物としてエポキシ化合物を含有させることにより上記課題を解決できることを見出し、本発明を完成するに至った。具体的には、本発明は以下のようなものを提供する。 The inventors of the present invention have made extensive studies to achieve the above object. As a result, it has been found that the above problems can be solved by including an epoxy compound as a binder compound of the colored photosensitive resin composition, and the present invention has been completed. Specifically, the present invention provides the following.
本発明の第一の態様は、(A)バインダー化合物、(B)光重合性モノマー、(C)光重合開始剤、及び(D)着色剤を含有し、前記(A)バインダー化合物がエポキシ化合物を含むタッチパネル用着色感光性樹脂組成物である。 A first aspect of the present invention includes (A) a binder compound, (B) a photopolymerizable monomer, (C) a photopolymerization initiator, and (D) a colorant, and the (A) binder compound is an epoxy compound. It is the coloring photosensitive resin composition for touchscreens containing.
本発明の第二の態様は、第一の態様におけるタッチパネル用着色感光性樹脂組成物を用いて形成された硬化樹脂パターンを有するタッチパネルである。 The second aspect of the present invention is a touch panel having a cured resin pattern formed using the colored photosensitive resin composition for a touch panel in the first aspect.
本発明の第二の態様は、第二の態様におけるタッチパネルを備えた表示装置である。 The 2nd aspect of this invention is a display apparatus provided with the touch panel in a 2nd aspect.
本発明によれば、耐薬品性、耐候性に優れ、タッチパネル用途に好適に用いられるタッチパネル用着色感光性樹脂組成物、そのタッチパネル用着色感光性樹脂組成物を用いて形成された硬化樹脂パターンを有するタッチパネル、及びそのタッチパネルを備えた表示装置を提供することができる。 According to the present invention, a colored photosensitive resin composition for a touch panel that is excellent in chemical resistance and weather resistance and is suitably used for touch panel applications, and a cured resin pattern formed using the colored photosensitive resin composition for a touch panel. A touch panel having the touch panel and a display device including the touch panel can be provided.
≪タッチパネル用着色感光性樹脂組成物≫
本発明に係るタッチパネル用着色感光性樹脂組成物(以下、単に「着色感光性樹脂組成物」という。)は、(A)バインダー化合物、(B)光重合性モノマー、(C)光重合開始剤、及び(D)着色剤を含有するものである。以下、着色感光性樹脂組成物に含有される各成分について説明する。
≪Colored photosensitive resin composition for touch panel≫
The colored photosensitive resin composition for touch panels according to the present invention (hereinafter simply referred to as “colored photosensitive resin composition”) includes (A) a binder compound, (B) a photopolymerizable monomer, and (C) a photopolymerization initiator. And (D) a coloring agent is contained. Hereinafter, each component contained in the colored photosensitive resin composition will be described.
<(A)バインダー化合物>
本発明に係る着色感光性樹脂組成物は、(A)バインダー化合物(以下、「(A)成分」ともいう。)としてエポキシ化合物を含有する。
<(A) Binder compound>
The colored photosensitive resin composition according to the present invention contains an epoxy compound as a binder compound (A) (hereinafter also referred to as “component (A)”).
エポキシ化合物としては、特に限定されず、バインダーとして機能する従来公知のエポキシ化合物を用いることができるが、その中でも、耐薬品性、耐候性の観点から下記式(A−1)で表されるエポキシ化合物が好ましい。
上記式(A−1)中、Ra1は、活性水素基を有する有機化合物中の活性水素基を除いた残基であるが、その前駆体である活性水素基を有する有機化合物としては、アルコール類、フェノール類、カルボン酸類、アミン類、チオール類等が挙げられる。 In the above formula (A-1), R a1 is a residue obtained by removing an active hydrogen group in an organic compound having an active hydrogen group, and an organic compound having an active hydrogen group as a precursor thereof is an alcohol. , Phenols, carboxylic acids, amines, thiols and the like.
上記アルコール類としては、1価のアルコールでも多価アルコールでもよい。具体的には、メタノール、エタノール、プロパノール、ブタノール、ペンタノール、ヘキサノール、オクタノール等の脂肪族アルコール;ベンジルアルコール等の芳香族アルコール;エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、1,3−ブタンジオール、1,4−ブタンジオール、ペンタンジオール、1,6−ヘキサンジオール、ネオペンチルグリコール、ヒドロキシピバリン酸ネオペンチルグリコールエステル、シクロヘキサンジメタノール、グリセリン、ジグリセリン、ポリグリセリン、トリメチロールプロパン、トリメチロールエタン、ペンタエリスリトール、ジペンタエリスリトール等の多価アルコール;等が挙げられる。
上記フェノール類としては、フェノール、クレゾール、カテコール、ピロガロール、ハイドロキノン、ハイドロキノンモノメチルエーテル、ビスフェノールA、ビスフェノールF、4,4’−ジヒドロキシベンゾフェノン、ビスフェノールS、フェノール樹脂、クレゾールノボラック樹脂等が挙げられる。
上記カルボン酸類としては、ギ酸、酢酸、プロピオン酸、酪酸、動植物油の脂肪酸、フマル酸、マレイン酸、アジピン酸、ドデカン二酸、トリメリット酸、ピロメリット酸、ポリアクリル酸、フタル酸、イソフタル酸、テレフタル酸等が挙げられる。また、乳酸、クエン酸、オキシカプロン酸等の、水酸基とカルボキシル基とを共に有する化合物も挙げられる。
上記アミン類としては、モノメチルアミン、ジメチルアミン、モノエチルアミン、ジエチルアミン、プロピルアミン、モノブチルアミン、ジブチルアミン、ペンチルアミン、ヘキシルアミン、シクロヘキシルアミン、オクチルアミン、ドデシルアミン、4,4’−ジアミノジフェニルメタン、イソホロンジアミン、トルエンジアミン、ヘキサメチレンジアミン、キシレンジアミン、ジエチレントリアミン、トリエチレンテトラミン、エタノールアミン等が挙げられる。
上記チオール類としては、メチルメルカプタン、エチルメルカプタン、プロピルメルカプタン、フェニルメルカプタン等のメルカプト類;エチレングリコールジメルカプトプロピオン酸エステル、トリメチロールプロパントリメルカプトプロピオン酸エステル、ペンタエリスリトールテトラメルカプトプロピオン酸エステル等の、メルカプトプロピオン酸又はメルカプトプロピオン酸の多価アルコールエステル;等が挙げられる。
The alcohols may be monohydric alcohols or polyhydric alcohols. Specifically, aliphatic alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, octanol; aromatic alcohols such as benzyl alcohol; ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene Glycol, 1,3-butanediol, 1,4-butanediol, pentanediol, 1,6-hexanediol, neopentyl glycol, hydroxypivalic acid neopentyl glycol ester, cyclohexanedimethanol, glycerin, diglycerin, polyglycerin, And polyhydric alcohols such as trimethylolpropane, trimethylolethane, pentaerythritol and dipentaerythritol.
Examples of the phenols include phenol, cresol, catechol, pyrogallol, hydroquinone, hydroquinone monomethyl ether, bisphenol A, bisphenol F, 4,4′-dihydroxybenzophenone, bisphenol S, a phenol resin, and a cresol novolac resin.
The above carboxylic acids include formic acid, acetic acid, propionic acid, butyric acid, fatty acids of animal and vegetable oils, fumaric acid, maleic acid, adipic acid, dodecanedioic acid, trimellitic acid, pyromellitic acid, polyacrylic acid, phthalic acid, isophthalic acid And terephthalic acid. Moreover, the compound which has both a hydroxyl group and a carboxyl group, such as lactic acid, a citric acid, and oxycaproic acid, is also mentioned.
Examples of the amines include monomethylamine, dimethylamine, monoethylamine, diethylamine, propylamine, monobutylamine, dibutylamine, pentylamine, hexylamine, cyclohexylamine, octylamine, dodecylamine, 4,4'-diaminodiphenylmethane, isophorone. Examples include diamine, toluene diamine, hexamethylene diamine, xylene diamine, diethylenetriamine, triethylenetetramine, and ethanolamine.
Examples of the thiols include mercapto such as methyl mercaptan, ethyl mercaptan, propyl mercaptan, and phenyl mercaptan; mercapto such as ethylene glycol dimercaptopropionate, trimethylolpropane trimercaptopropionate, pentaerythritol tetramercaptopropionate And propionic acid or mercaptopropionic acid polyhydric alcohol ester.
さらに、活性水素基を有する有機化合物としては、ポリビニルアルコール、ポリ酢酸ビニル部分加水分解物、デンプン、セルロース、セルロースアセテート、セルロースアセテートブチレート、ヒドロキシエチルセルロース、アクリルポリオール樹脂、スチレンアリルアルコール共重合樹脂、スチレン−マレイン酸共重合樹脂、アルキッド樹脂、ポリエステルポリオール樹脂、ポリエステルカルボン酸樹脂、ポリカプロラクトンポリオール樹脂、ポリプロピレンポリオール、ポリテトラメチレングリコール等も挙げられる。 In addition, organic compounds having active hydrogen groups include polyvinyl alcohol, polyvinyl acetate partial hydrolyzate, starch, cellulose, cellulose acetate, cellulose acetate butyrate, hydroxyethyl cellulose, acrylic polyol resin, styrene allyl alcohol copolymer resin, styrene. -Maleic acid copolymer resin, alkyd resin, polyester polyol resin, polyester carboxylic acid resin, polycaprolactone polyol resin, polypropylene polyol, polytetramethylene glycol and the like can also be mentioned.
この活性水素基を有する有機化合物は、その骨格中に不飽和二重結合を有していてもよい。具体例としては、アリルアルコール、アクリル酸、メタクリル酸、3−シクロヘキセンメタノール、テトラヒドロフタル酸等が挙げられる。
以上の活性水素基を有する有機化合物は、単独又は2種以上組み合わせて用いることができる。
The organic compound having an active hydrogen group may have an unsaturated double bond in its skeleton. Specific examples include allyl alcohol, acrylic acid, methacrylic acid, 3-cyclohexenemethanol, tetrahydrophthalic acid and the like.
These organic compounds having an active hydrogen group can be used alone or in combination of two or more.
上記式(A−1)中、n1,n2,・・・,nkは、それぞれ独立に0〜100の整数を示し、その和は1〜100である。また、kは1〜100の整数を示す。
n1,n2,・・・,nkは、それぞれ独立に2〜10の整数が好ましく、3〜6の整数がより好ましい。また、n1,n2,・・・,nkの和は、4〜30であることが好ましく、4〜20であることがより好ましい。上記和を4以上とすることにより、硬化後の架橋密度を高め、硬度を高めることができる。また、上記和を30以下とすることにより、溶剤への溶解性を高め、ハンドリング性を高めることができる。
In the above formula (A-1), n1, n2,..., Nk each independently represents an integer of 0-100, and the sum thereof is 1-100. Moreover, k shows the integer of 1-100.
n1, n2,..., nk are each independently preferably an integer of 2 to 10, more preferably an integer of 3 to 6. Moreover, it is preferable that it is 4-30, and, as for the sum of n1, n2, ..., nk, it is more preferable that it is 4-20. By setting the sum to 4 or more, the crosslinking density after curing can be increased and the hardness can be increased. Moreover, by making the said sum 30 or less, the solubility to a solvent can be improved and handling property can be improved.
上記式(A−1)中、Aは、置換基Bを有するオキシシクロヘキサン骨格又は置換基Bを有するオキシノルボルネン骨格であり、上記式(A−2)又は(A−3)で表される。Aは、上記式(A−2)で表されることが好ましい。なお、k個あるAはそれぞれ同一であっても異なっていてもよい。 In the above formula (A-1), A is an oxycyclohexane skeleton having a substituent B or an oxynorbornene skeleton having a substituent B, and is represented by the above formula (A-2) or (A-3). A is preferably represented by the above formula (A-2). The k A's may be the same or different.
上記式(A−1)で表されるエポキシ化合物中には、上記式(A−4)で表される基が1個以上含まれることが必須であり、多ければ多いほど好ましい。一方、上記式(A−6)で表される基は少なければ少ないほど好ましい。 It is essential that the epoxy compound represented by the above formula (A-1) contains at least one group represented by the above formula (A-4). On the other hand, the fewer groups represented by the above formula (A-6), the better.
上記式(A−1)で表されるエポキシ化合物は、特公平7−119270号公報におけるように、活性水素基を有する有機化合物を開始剤にして、4−ビニルシクロヘキセン−1−オキシド又は5−ビニルビシクロ[2.2.1]ヘプト−2−エン−2−オキシドとエポキシ基を1個有する化合物との混合物を開環重合させることによって得られるポリエーテル樹脂、すなわち、ビニル基側鎖及びシクロヘキサン骨格、あるいはビニル基側鎖及びノルボルネン骨格を有するポリエーテル樹脂を、過酢酸や過酸化水素等でエポキシ化することにより製造される。
市販品としては、ダイセル化学工業社製のEHPE3150(n1〜nkの和が平均15)が好適なものとして挙げられる。
The epoxy compound represented by the above formula (A-1) is prepared by using an organic compound having an active hydrogen group as an initiator, as disclosed in Japanese Patent Publication No. 7-119270, or 4-vinylcyclohexene-1-oxide or 5- Polyether resin obtained by ring-opening polymerization of a mixture of vinylbicyclo [2.2.1] hept-2-ene-2-oxide and a compound having one epoxy group, ie, vinyl group side chain and cyclohexane It is produced by epoxidizing a polyether resin having a skeleton or a vinyl group side chain and a norbornene skeleton with peracetic acid or hydrogen peroxide.
As a commercial item, EHPE3150 (the sum of n1 to nk is 15 on average) manufactured by Daicel Chemical Industries, Ltd. is preferable.
また、エポキシ化合物としては、脂環式エポキシ化合物を用いることもできる。
脂環式エポキシ化合物としては、3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレート、2−(3,4−エポキシシクロヘキシル−5,5−スピロ−3,4−エポキシ)シクロヘキサン−メタ−ジオキサン、ビス(3,4−エポキシシクロヘキシルメチル)アジペート、ビス(3,4−エポキシ−6−メチルシクロヘキシルメチル)アジペート、3,4−エポキシ−6−メチルシクロヘキシル−3’,4’−エポキシ−6’−メチルシクロヘキサンカルボキシレート、ε−カプロラクトン変性3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレート、トリメチルカプロラクトン変性3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレート、β−メチル−δ−バレロラクトン変性3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレート、メチレンビス(3,4−エポキシシクロヘキサン)、エチレングリコールのジ(3,4−エポキシシクロヘキシルメチル)エーテル、エチレンビス(3,4−エポキシシクロヘキサンカルボキシレート)、エポキシシクロヘキサヒドロフタル酸ジオクチル、エポキシシクロヘキサヒドロフタル酸ジ−2−エチルヘキシル等が挙げられる。
市販品としては、ダイセル化学工業社製のセロキサイド2021,2021P,2081,2083,2085、エポリードGT−300,GT−301,GT−302,GT−400,401,403等や、新日化エポキシ製造社製のサントートST−3000,ST−4000,ST−5080,ST−5100等が好適なものとして挙げられる。
Moreover, as an epoxy compound, an alicyclic epoxy compound can also be used.
As the alicyclic epoxy compound, 3,4-epoxycyclohexylmethyl-3 ′, 4′-epoxycyclohexanecarboxylate, 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane Meta-dioxane, bis (3,4-epoxycyclohexylmethyl) adipate, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexyl-3 ′, 4′- Epoxy-6′-methylcyclohexanecarboxylate, ε-caprolactone-modified 3,4-epoxycyclohexylmethyl-3 ′, 4′-epoxycyclohexanecarboxylate, trimethylcaprolactone-modified 3,4-epoxycyclohexylmethyl-3 ′, 4′- Epoxy cyclohexane carbo Sylate, β-methyl-δ-valerolactone modified 3,4-epoxycyclohexylmethyl-3 ′, 4′-epoxycyclohexanecarboxylate, methylene bis (3,4-epoxycyclohexane), di (3,4-epoxy) of ethylene glycol (Cyclohexylmethyl) ether, ethylene bis (3,4-epoxycyclohexanecarboxylate), epoxycyclohexahydrophthalate dioctyl, epoxycyclohexahydrophthalate di-2-ethylhexyl, and the like.
Commercially available products include Celoxide 2021, 2021P, 2081, 2083, 2085 manufactured by Daicel Chemical Industries, Epolide GT-300, GT-301, GT-302, GT-400, 401, 403, etc. Santo Tote ST-3000, ST-4000, ST-5080, ST-5100, etc., manufactured by the company are preferred.
さらに、エポキシ化合物としては、ノボラック型エポキシ化合物、ビスフェノールA型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビフェニル型エポキシ化合物等を用いることもできる。 Furthermore, as an epoxy compound, a novolak type epoxy compound, a bisphenol A type epoxy compound, a cresol novolak type epoxy compound, a biphenyl type epoxy compound, or the like can also be used.
上記ノボラック型エポキシ化合物としては、エポキシ当量が200〜220のものが好ましい。市販品としては、大日本インキ社製のエピクロンN−660,N−665,N−670,N−673,N−680,N−690,N−695,N−685−EXP,N−672−EXP,N−655−EXP−S,N−865,N−865−80M,YDCN−701,YDCN−702,YDCN−703,YDCN−704,YDCN−704L等が挙げられる。
上記ビスフェノールA型エポキシ化合物の市販品としては、新日化エポキシ製造社製のエポトートYD−115,YD−118T,YD−127,YD−128,YD−134,YD−8125,YD−7011R,ZX−1059,YDF−8170,YDF−170等や、ナガセケムテックス社製のデナコールEX−1101,EX−1102,EX−1103等や、ダイセル化学工業社製のプラクセルGL−61,GL−62,G101,G102等が挙げられる。
上記クレゾールノボラック型エポキシ化合物の市販品としては、新日化エポキシ製造社製のエポトートYDPN−638,YDPN−701,YDPN−702,YDPN−703,YDPN−704等や、ナガセケムテックス社製のデナコールEM−125等が挙げられる。
上記ビフェニル型エポキシ化合物としては、3,5,3’,5’−テトラメチル−4,4’−ジグリシジルビフェニル等が挙げられる。
As said novolak-type epoxy compound, that whose epoxy equivalent is 200-220 is preferable. Examples of commercially available products include Epicron N-660, N-665, N-670, N-673, N-680, N-690, N-695, N-685-EXP, and N-672, manufactured by Dainippon Ink. EXP, N-655-EXP-S, N-865, N-865-80M, YDCN-701, YDCN-702, YDCN-703, YDCN-704, YDCN-704L, and the like.
Commercially available products of the above bisphenol A type epoxy compounds include EPOTOTO YD-115, YD-118T, YD-127, YD-128, YD-134, YD-8125, YD-7011R, ZX manufactured by Nippon Kayaku Epoxy Manufacturing Co., Ltd. -1059, YDF-8170, YDF-170, etc., Denasel EX-1101, EX-1102, EX-1103 etc. manufactured by Nagase ChemteX Corporation, Plaxel GL-61, GL-62, G101 manufactured by Daicel Chemical Industries, Ltd. , G102 and the like.
Examples of commercially available cresol novolac epoxy compounds include Epototo YDPN-638, YDPN-701, YDPN-702, YDPN-703, and YDPN-704 manufactured by Nippon Kayaku Epoxy Manufacturing Co., Ltd. and Denacol manufactured by Nagase ChemteX Corporation. EM-125 etc. are mentioned.
Examples of the biphenyl type epoxy compound include 3,5,3 ′, 5′-tetramethyl-4,4′-diglycidylbiphenyl and the like.
本発明に係る着色感光性樹脂組成物は、上記エポキシ化合物に加えて、他のバインダー化合物をさらに含有することが好ましい。このような他のバインダー化合物としては、(メタ)アクリル酸、フマル酸、マレイン酸、フマル酸モノメチル、フマル酸モノエチル、2−ヒドロキシエチル(メタ)アクリレート、エチレングリコールモノメチルエーテル(メタ)アクリレート、エチレングリコールモノエチルエーテル(メタ)アクリレート、グリセロール(メタ)アクリレート、(メタ)アクリルアミド、アクリロニトリル、メタクリロニトリル、メチル(メタ)アクリレート、エチル(メタ)アクリレート、イソブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、ベンジル(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジアクリレート、トリエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ブチレングリコールジメタクリレート、プロピレングリコールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、テトラメチロールプロパンテトラ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、カルドエポキシジアクリレート等が重合したオリゴマー類;多価アルコール類と一塩基酸又は多塩基酸とを縮合して得られるポリエステルプレポリマーに(メタ)アクリル酸を反応させて得られるポリエステル(メタ)アクリレート;ポリオールと2個のイソシアネート基を持つ化合物とを反応させた後、(メタ)アクリル酸を反応させて得られるポリウレタン(メタ)アクリレート;ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、フェノール又はクレゾールノボラック型エポキシ樹脂、レゾール型エポキシ樹脂、トリフェノールメタン型エポキシ樹脂、ポリカルボン酸ポリグリシジルエステル、ポリオールポリグリシジルエステル、脂肪族又は脂環式エポキシ樹脂、アミンエポキシ樹脂、ジヒドロキシベンゼン型エポキシ樹脂等のエポキシ樹脂と、(メタ)アクリル酸とを反応させて得られるエポキシ(メタ)アクリレート樹脂等が挙げられる。さらに、エポキシ(メタ)アクリレート樹脂に多塩基酸無水物を反応させた樹脂も好適に用いることができる。 It is preferable that the colored photosensitive resin composition according to the present invention further contains another binder compound in addition to the epoxy compound. Examples of such other binder compounds include (meth) acrylic acid, fumaric acid, maleic acid, monomethyl fumarate, monoethyl fumarate, 2-hydroxyethyl (meth) acrylate, ethylene glycol monomethyl ether (meth) acrylate, and ethylene glycol. Monoethyl ether (meth) acrylate, glycerol (meth) acrylate, (meth) acrylamide, acrylonitrile, methacrylonitrile, methyl (meth) acrylate, ethyl (meth) acrylate, isobutyl (meth) acrylate, 2-ethylhexyl (meth) acrylate , Benzyl (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol diacrylate, triethylene glycol di (meth) acrylate, tetrae Lenglycol di (meth) acrylate, butylene glycol dimethacrylate, propylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, tetramethylolpropane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra Oligomers in which (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 1,6-hexanediol di (meth) acrylate, cardoepoxy diacrylate, etc. are polymerized; polyhydric alcohols (Meth) acrylate obtained by reacting (meth) acrylic acid with polyester prepolymer obtained by condensing monobasic acid or polybasic acid with G: polyurethane (meth) acrylate obtained by reacting a polyol with a compound having two isocyanate groups and then reacting with (meth) acrylic acid; bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S Type epoxy resin, phenol or cresol novolac type epoxy resin, resol type epoxy resin, triphenolmethane type epoxy resin, polycarboxylic acid polyglycidyl ester, polyol polyglycidyl ester, aliphatic or cycloaliphatic epoxy resin, amine epoxy resin, dihydroxy Examples thereof include an epoxy (meth) acrylate resin obtained by reacting an epoxy resin such as a benzene type epoxy resin with (meth) acrylic acid. Furthermore, a resin obtained by reacting an epoxy (meth) acrylate resin with a polybasic acid anhydride can also be suitably used.
また、他のバインダー化合物としては、エポキシ化合物と不飽和基含有カルボン酸化合物との反応物を、さらに多塩基酸無水物と反応させることにより得られる樹脂も好適に用いることができる。その中でも、それ自体の硬化性が高い点で、下記式(A−7)で表される化合物が好ましい。
上記式(A−7)中、Xは、下記式(A−8)で表される基を示す。
上記式(A−8)中、Ra3は、それぞれ独立に水素原子、炭素数1〜6の炭化水素基、又はハロゲン原子を示し、Ra4は、それぞれ独立に水素原子又はメチル基を示し、Wは、単結合又は下記式(A−9)で表される基を示す。
また、上記式(A−7)中、Yは、ジカルボン酸無水物から酸無水物基(−CO−O−CO−)を除いた残基を示す。ジカルボン酸無水物の例としては、無水マレイン酸、無水コハク酸、無水イタコン酸、無水フタル酸、無水テトラヒドロフタル酸、無水ヘキサヒドロフタル酸、無水メチルエンドメチレンテトラヒドロフタル酸、無水クロレンド酸、メチルテトラヒドロ無水フタル酸、無水グルタル酸等が挙げられる。 Moreover, in said formula (A-7), Y shows the residue remove | excluding the acid anhydride group (-CO-O-CO-) from the dicarboxylic anhydride. Examples of dicarboxylic acid anhydrides include maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, chlorendic anhydride, methyltetrahydro Examples thereof include phthalic anhydride and glutaric anhydride.
また、上記式(A−7)中、Zは、テトラカルボン酸二無水物から2個の酸無水物基を除いた残基を示す。テトラカルボン酸二無水物の例としては、無水ピロメリット酸、ベンゾフェノンテトラカルボン酸二無水物、ビフェニルテトラカルボン酸二無水物、ビフェニルエーテルテトラカルボン酸二無水物等が挙げられる。
また、上記式(A−7)中、mは、0〜20の整数を示す。
Moreover, in said formula (A-7), Z shows the residue remove | excluding two acid anhydride groups from tetracarboxylic dianhydride. Examples of tetracarboxylic dianhydrides include pyromellitic anhydride, benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, biphenyl ether tetracarboxylic dianhydride, and the like.
Moreover, in said formula (A-7), m shows the integer of 0-20.
上記式(A−7)で表される化合物の酸価は、樹脂固形分で、10〜150mgKOH/gであることが好ましく、70〜110mgKOH/gであることがより好ましい。酸価を10mgKOH/g以上とすることにより、十分な現像性が得られる。また、酸価を150mgKOH/g以下とすることにより、十分な硬化性を得ることができ、表面性を良好にすることができる。 The acid value of the compound represented by the above formula (A-7) is preferably 10 to 150 mgKOH / g, more preferably 70 to 110 mgKOH / g in terms of resin solids. Sufficient developability can be obtained by setting the acid value to 10 mgKOH / g or more. Moreover, by making an acid value into 150 mgKOH / g or less, sufficient sclerosis | hardenability can be obtained and surface property can be made favorable.
また、上記式(A−7)で表される化合物の質量平均分子量は、1000〜40000であることが好ましく、2000〜30000であることがより好ましい。質量平均分子量を1000以上とすることにより、耐熱性、膜強度を向上させることができる。また、質量平均分子量を40000以下とすることにより、現像液に対する十分な溶解性を得ることができる。 Moreover, it is preferable that it is 1000-40000, and, as for the mass mean molecular weight of the compound represented by the said Formula (A-7), it is more preferable that it is 2000-30000. By setting the mass average molecular weight to 1000 or more, heat resistance and film strength can be improved. Moreover, sufficient solubility with respect to a developing solution can be acquired by making a mass mean molecular weight into 40000 or less.
(A)成分の含有量は、本発明に係る着色感光性樹脂組成物の固形分に対して30〜90質量%であることが好ましく、50〜70質量%であることがより好ましい。また、(A)成分の全量に対するエポキシ化合物の割合は、30〜70質量%であることが好ましく、40〜60質量%であることがより好ましい。エポキシ化合物の割合を30質量%以上とすることにより、耐薬品性、耐候性を向上させることができる。また、エポキシ化合物の割合を70質量%以下とすることにより、感度・現像性の低下を抑えることができる。 The content of the component (A) is preferably 30 to 90% by mass and more preferably 50 to 70% by mass with respect to the solid content of the colored photosensitive resin composition according to the present invention. Moreover, it is preferable that the ratio of the epoxy compound with respect to the whole quantity of (A) component is 30-70 mass%, and it is more preferable that it is 40-60 mass%. By setting the ratio of the epoxy compound to 30% by mass or more, chemical resistance and weather resistance can be improved. Moreover, the fall of a sensitivity and developability can be suppressed by the ratio of an epoxy compound being 70 mass% or less.
<(B)光重合性モノマー>
(B)光重合性モノマー(以下、「(B)成分」ともいう。)としては、特に限定されず、従来公知の単官能モノマーや多官能モノマーを用いることができる。
<(B) Photopolymerizable monomer>
(B) As a photopolymerizable monomer (henceforth "(B) component"), it does not specifically limit, A conventionally well-known monofunctional monomer and polyfunctional monomer can be used.
上記単官能モノマーとしては、(メタ)アクリルアミド、メチロール(メタ)アクリルアミド、メトキシメチル(メタ)アクリルアミド、エトキシメチル(メタ)アクリルアミド、プロポキシメチル(メタ)アクリルアミド、ブトキシメトキシメチル(メタ)アクリルアミド、N−メチロール(メタ)アクリルアミド、N−ヒドロキシメチル(メタ)アクリルアミド、(メタ)アクリル酸、フマル酸、マレイン酸、無水マレイン酸、イタコン酸、無水イタコン酸、シトラコン酸、無水シトラコン酸、クロトン酸、2−アクリルアミド−2−メチルプロパンスルホン酸、tert−ブチルアクリルアミドスルホン酸、メチル(メタ)アクリレート、エチル(メタ)アクリレート、ブチル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、2−ヒドロキシブチル(メタ)アクリレート、2−フェノキシ−2−ヒドロキシプロピル(メタ)アクリレート、2−(メタ)アクリロイルオキシ−2−ヒドロキシプロピルフタレート、グリセリンモノ(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、ジメチルアミノ(メタ)アクリレート、グリシジル(メタ)アクリレート、2,2,2−トリフルオロエチル(メタ)アクリレート、2,2,3,3−テトラフルオロプロピル(メタ)アクリレート、フタル酸誘導体のハーフ(メタ)アクリレート等が挙げられる。これらの単官能モノマーは、単独又は2種以上組み合わせて用いることができる。 Examples of the monofunctional monomer include (meth) acrylamide, methylol (meth) acrylamide, methoxymethyl (meth) acrylamide, ethoxymethyl (meth) acrylamide, propoxymethyl (meth) acrylamide, butoxymethoxymethyl (meth) acrylamide, and N-methylol. (Meth) acrylamide, N-hydroxymethyl (meth) acrylamide, (meth) acrylic acid, fumaric acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, crotonic acid, 2-acrylamide 2-methylpropanesulfonic acid, tert-butylacrylamidesulfonic acid, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate Rate, cyclohexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-phenoxy-2-hydroxypropyl (meth) acrylate, 2- (Meth) acryloyloxy-2-hydroxypropyl phthalate, glycerin mono (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, dimethylamino (meth) acrylate, glycidyl (meth) acrylate, 2,2,2-trifluoroethyl ( And (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, and half (meth) acrylate of a phthalic acid derivative. These monofunctional monomers can be used alone or in combination of two or more.
一方、上記多官能モノマーとしては、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、ブチレングリコールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、1,6−ヘキサングリコールジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、グリセリンジ(メタ)アクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、ジペンタエリスリトールペンタアクリレート、ジペンタエリスリトールヘキサアクリレート、ペンタエリスリトールジ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、2,2−ビス(4−(メタ)アクリロキシジエトキシフェニル)プロパン、2,2−ビス(4−(メタ)アクリロキシポリエトキシフェニル)プロパン、2−ヒドロキシ−3−(メタ)アクリロイルオキシプロピル(メタ)アクリレート、エチレングリコールジグリシジルエーテルジ(メタ)アクリレート、ジエチレングリコールジグリシジルエーテルジ(メタ)アクリレート、フタル酸ジグリシジルエステルジ(メタ)アクリレート、グリセリントリアクリレート、グリセリンポリグリシジルエーテルポリ(メタ)アクリレート、ウレタン(メタ)アクリレート(すなわち、トリレンジイソシアネート)、トリメチルヘキサメチレンジイソシアネートとヘキサメチレンジイソシアネート等と2−ビドロキシエチル(メタ)アクリレートとの反応物、メチレンビス(メタ)アクリルアミド、(メタ)アクリルアミドメチレンエーテル、多価アルコールとN−メチロール(メタ)アクリルアミドとの縮合物等の多官能モノマーや、トリアクリルホルマール等が挙げられる。これらの多官能モノマーは、単独又は2種以上組み合わせて用いることができる。 On the other hand, as the above polyfunctional monomer, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene Glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6-hexane glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, glycerin di (meth) acrylate, pentaerythritol triacrylate, penta Erythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol di ( ) Acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, 2,2-bis (4- (meth) acryl Roxydiethoxyphenyl) propane, 2,2-bis (4- (meth) acryloxypolyethoxyphenyl) propane, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, ethylene glycol diglycidyl ether di ( (Meth) acrylate, diethylene glycol diglycidyl ether di (meth) acrylate, diglycidyl phthalate di (meth) acrylate, glycerin triacrylate, glycerin polyglycidyl ether Re (meth) acrylate, urethane (meth) acrylate (ie, tolylene diisocyanate), reaction product of trimethylhexamethylene diisocyanate and hexamethylene diisocyanate and 2-bidoxyethyl (meth) acrylate, methylenebis (meth) acrylamide, (meth) Examples thereof include polyfunctional monomers such as acrylamide methylene ether, polyhydric alcohol and N-methylol (meth) acrylamide condensate, and triacryl formal. These polyfunctional monomers can be used alone or in combination of two or more.
(B)成分の含有量は、(A)成分に対して20〜60質量%であることが好ましく、30〜50質量%であることがより好ましい。上記範囲内とすることにより、硬化性を向上させ、パターン形成を容易にすることができる。 The content of the component (B) is preferably 20 to 60% by mass and more preferably 30 to 50% by mass with respect to the component (A). By setting it within the above range, curability can be improved and pattern formation can be facilitated.
<(C)光重合開始剤>
(C)光重合開始剤(以下、「(C)成分」ともいう。)としては、特に限定されず、従来公知の光重合開始剤を用いることができる。このような光重合開始剤としては、アセトフェノン、2,2−ジエトキシアセトフェノン、p−ジメチルアセトフェノン、p−ジメチルアミノプロピオフェノン、ジクロロアセトフェノン、トリクロロアセトフェノン、p−tert−ブチルアセトフェノン等のアセトフェノン類;ベンゾフェノン、2−クロロベンゾフェノン、p,p’−ビスジメチルアミノベンゾフェノン等のベンゾフェノン類;ベンゾインメチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル等のベンゾインエ−テル類;チオキサンテン、2−クロロチオキサンテン、2,4−ジエチルチオキサンテン、2−メチルチオキサンテン、2−イソプロピルチオキサンテン等の硫黄化合物;2−エチルアントラキノン、オクタメチルアントラキノン、1,2−ベンズアントラキノン、2,3−ジフェニルアントラキノン等のアントラキノン類;ベンゾイルパーオキシド、クメンパーオキシド等の有機過酸化物;2−メルカプトベンゾイミダール、2−メルカプトベンゾオキサゾール、2−メルカプトベンゾチアゾール等のチオール化合物;2−(o−クロロフェニル)−4,5−ジ(m−メトキシフェニル)−イミダゾリル二量体等のイミダゾリル化合物;p−メトキシトリアジン等のトリアジン化合物;2,4,6−トリス(トリクロロメチル)−s−トリアジン、2−メチル−4,6−ビス(トリクロロメチル)−s−トリアジン、2−[2−(5−メチルフラン−2−イル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−[2−(フラン−2−イル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−[2−(4−ジエチルアミノ−2−メチルフェニル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−[2−(3,4−ジメトキシフェニル)エテニル]−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−メトキシフェニル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−エトキシスチリル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−n−ブトキシフェニル)−4,6−ビス(トリクロロメチル)−s−トリアジン等のハロメチル基を有するトリアジン化合物;2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタン−1−オン等のアミノケトン化合物;エタノン−1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル]−1−(O−アセチルオキシム)等のオキシムエステル化合物;等が挙げられる。
<(C) Photopolymerization initiator>
(C) It does not specifically limit as a photoinitiator (henceforth "(C) component"), A conventionally well-known photoinitiator can be used. Examples of such a photopolymerization initiator include acetophenones such as acetophenone, 2,2-diethoxyacetophenone, p-dimethylacetophenone, p-dimethylaminopropiophenone, dichloroacetophenone, trichloroacetophenone, and p-tert-butylacetophenone; Benzophenones such as benzophenone, 2-chlorobenzophenone, p, p'-bisdimethylaminobenzophenone; benzoin ethers such as benzoin methyl ether, benzoin isopropyl ether, benzoin isobutyl ether; thioxanthene, 2-chlorothioxanthene, 2, Sulfur compounds such as 4-diethylthioxanthene, 2-methylthioxanthene, 2-isopropylthioxanthene; 2-ethylanthraquinone, octamethylanthraquinone Anthraquinones such as 1,2-benzanthraquinone and 2,3-diphenylanthraquinone; Organic peroxides such as benzoyl peroxide and cumene peroxide; 2-mercaptobenzoimidar, 2-mercaptobenzoxazole, 2-mercaptobenzo Thiol compounds such as thiazole; imidazolyl compounds such as 2- (o-chlorophenyl) -4,5-di (m-methoxyphenyl) -imidazolyl dimer; triazine compounds such as p-methoxytriazine; 2,4,6- Tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [2- (5-methylfuran-2-yl) ethenyl] -4,6- Bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) eth L] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2 -[2- (3,4-Dimethoxyphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl) -s- Triazine, 2- (4-ethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-n-butoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, etc. A triazine compound having a halomethyl group; an aminoketone compound such as 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; Thanon -1- [9-ethyl-6- (2-methylbenzoyl) -9H- carbazol-3-yl] -1- (O-acetyl oxime) oxime ester compounds and the like; and the like.
これらの中でも、着色感光性樹脂組成物の感度を十分に保ち、パターンの直進性を向上させる観点から、オキシムエステル化合物が好ましい。このようなオキシムエステル化合物としては、下記式(C−1)で表されるものが好ましい。 Among these, an oxime ester compound is preferable from the viewpoint of sufficiently maintaining the sensitivity of the colored photosensitive resin composition and improving the straightness of the pattern. As such an oxime ester compound, what is represented by a following formula (C-1) is preferable.
上記式(C−1)中、Rc1は、−NO2又は−CORc5を示す。また、Rc5は、置換基を有していてもよい、複素環基、縮合環式芳香族基、又は芳香族基を示す。Rc2〜Rc4はそれぞれ独立に一価の有機基を示す。 In the above formula (C-1), R c1 represents —NO 2 or —COR c5 . R c5 represents a heterocyclic group, a condensed cyclic aromatic group, or an aromatic group, which may have a substituent. R c2 to R c4 each independently represent a monovalent organic group.
Rc5で表される複素環基としては、窒素原子、硫黄原子、及び酸素原子の少なくとも1つの原子を含む5員環以上、好ましくは5員環又は6員環の複素環基が挙げられる。複素環基の例としては、ピロリル基、イミダゾリル基、ピラゾリル基等の含窒素5員環基;ピリジル基、ピラジニル基、ピリミジル基、ピリダジニル基等の含窒素6員環基;チアゾリル基、イソチアゾリル基等の含窒素含硫黄基;オキサゾリル基、イソオキサゾリル基等の含窒素含酸素基;チエニル基、チオピラニル基等の含硫黄基;フリル基、ピラニル基等の含酸素基;等が挙げられる。この中でも、窒素原子又は硫黄原子を1つ含むものが好ましい。この複素環には縮合環が含まれていてもよい。縮合環が含まれる複素環基の例としてはベンゾチエニル基等が挙げられる。 Examples of the heterocyclic group represented by R c5 include a 5-membered ring or more, preferably a 5-membered or 6-membered heterocyclic group containing at least one atom of a nitrogen atom, a sulfur atom, and an oxygen atom. Examples of heterocyclic groups include nitrogen-containing 5-membered ring groups such as pyrrolyl, imidazolyl and pyrazolyl groups; nitrogen-containing 6-membered ring groups such as pyridyl, pyrazinyl, pyrimidyl and pyridazinyl groups; thiazolyl and isothiazolyl groups Nitrogen-containing sulfur groups such as oxazolyl groups and isoxazolyl groups; sulfur-containing groups such as thienyl groups and thiopyranyl groups; oxygen-containing groups such as furyl groups and pyranyl groups; Among these, those containing one nitrogen atom or one sulfur atom are preferable. This heterocyclic ring may contain a condensed ring. Examples of the heterocyclic group containing a condensed ring include a benzothienyl group.
Rc5で示される縮合環式芳香族基としては、ナフチル基、アントリル基、フェナントリル基等が挙げられる。また、Rc1で示される芳香族基としては、フェニル基が挙げられる。 Examples of the condensed cyclic aromatic group represented by R c5 include a naphthyl group, an anthryl group, and a phenanthryl group. Moreover, a phenyl group is mentioned as an aromatic group shown by Rc1 .
複素環基、縮合環式芳香族基、又は芳香族基は、置換基を有していてもよい。特にRc5が芳香族基である場合には、置換基を有していることが好ましい。このような置換基としては、−NO2、−CN、−SO2Rc6、−CORc6、−NRc7Rc8、−Rc9、−ORc9、−O−Rc10−O−Rc11等が挙げられる。 The heterocyclic group, the condensed cyclic aromatic group, or the aromatic group may have a substituent. In particular, when R c5 is an aromatic group, it preferably has a substituent. Examples of such substituent include —NO 2 , —CN, —SO 2 R c6 , —COR c6 , —NR c7 R c8 , —R c9 , —OR c9 , —O—R c10 —O—R c11, and the like. Is mentioned.
Rc6は、それぞれ独立にアルキル基を表し、これらはハロゲン原子で置換されていてもよく、エーテル結合、チオエーテル結合、エステル結合により中断されていてもよい。Rc6におけるアルキル基は、炭素数1〜5であることが好ましく、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基等が挙げられる。 R c6 each independently represents an alkyl group, which may be substituted with a halogen atom, and may be interrupted by an ether bond, a thioether bond, or an ester bond. The alkyl group for R c6 preferably has 1 to 5 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group.
Rc7、Rc8は、それぞれ独立に水素原子、アルキル基、又はアルコキシ基を表し、これらはハロゲン原子で置換されていてもよく、これらのうちアルキル基及びアルコキシ基のアルキレン部分は、エーテル結合、チオエーテル結合、又はエステル結合により中断されていてもよい。また、Rc7とRc8とが結合して環構造を形成していてもよい。Rc7、Rc8におけるアルキル基又はアルコキシ基は、炭素数1〜5であることが好ましく、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、メトキシ基、エトキシ基、プロポキシ基等が挙げられる。 R c7 and R c8 each independently represent a hydrogen atom, an alkyl group, or an alkoxy group, which may be substituted with a halogen atom, and among these, the alkylene part of the alkyl group and the alkoxy group is an ether bond, It may be interrupted by a thioether bond or an ester bond. R c7 and R c8 may be bonded to each other to form a ring structure. The alkyl group or alkoxy group in R c7 and R c8 preferably has 1 to 5 carbon atoms. For example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, methoxy group, ethoxy group, A propoxy group etc. are mentioned.
Rc7とRc8とが結合して形成し得る環構造としては、複素環が挙げられる。この複素環としては、少なくとも窒素原子を含む5員環以上、好ましくは5〜7員環の複素環が挙げられる。この複素環には縮合環が含まれていてもよい。複素環の例としては、ピペリジン環、モルホリン環、チオモルホリン環等が挙げられる。これらの中でも、モルホリン環が好ましい。 Examples of the ring structure that can be formed by combining R c7 and R c8 include a heterocyclic ring. Examples of the heterocyclic ring include 5-membered or more, preferably 5 to 7-membered heterocyclic rings containing at least a nitrogen atom. This heterocyclic ring may contain a condensed ring. Examples of the heterocyclic ring include piperidine ring, morpholine ring, thiomorpholine ring and the like. Among these, a morpholine ring is preferable.
Rc9は、水素原子の一部又は全部がハロゲン原子で置換されていてもよいアルキル基を表す。Rc9におけるアルキル基は、炭素数1〜5であることが好ましく、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基等が挙げられる。 R c9 represents an alkyl group in which some or all of the hydrogen atoms may be substituted with a halogen atom. The alkyl group for R c9 preferably has 1 to 5 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group.
Rc10、Rc11は、それぞれ独立にアルキル基を表し、これらはハロゲン原子で置換されていてもよく、エーテル結合、チオエーテル結合、エステル結合により中断されていてもよい。好ましい炭素数やその具体例は、上記Rc6の説明と同様である。 R c10 and R c11 each independently represent an alkyl group, which may be substituted with a halogen atom, and may be interrupted by an ether bond, a thioether bond, or an ester bond. Preferred carbon numbers and specific examples thereof are the same as those described above for R c6 .
これらの中でも、Rc5としては、ピロリル基、ピリジル基、チエニル基、チオピラリル基、ベンゾチエニル基、ナフチル基、置換基を有するフェニル基が好ましい例として挙げられる。 Among these, preferred examples of R c5 include a pyrrolyl group, a pyridyl group, a thienyl group, a thiopyralyl group, a benzothienyl group, a naphthyl group, and a phenyl group having a substituent.
上記式(C−1)中、Rc2は、一価の有機基を示す。この有機基としては、−Rc12、−ORc12、−CORc12、−SRc12、−NRc12Rc13で表される基が好ましい。Rc12、Rc13は、それぞれ独立にアルキル基、アルケニル基、アリール基、アラルキル基、又は複素環基を示し、これらはハロゲン原子、アルキル基、又は複素環基で置換されていてもよく、これらのうちアルキル基及びアラルキル基のアルキレン部分は、不飽和結合、エーテル結合、チオエーテル結合、エステル結合により中断されていてもよい。また、Rc12とRc13とが結合して窒素原子とともに環構造を形成していてもよい。 In the above formula (C-1), R c2 represents a monovalent organic group. The organic group is preferably a group represented by -R c12 , -OR c12 , -COR c12 , -SR c12 , -NR c12 R c13 . R c12 and R c13 each independently represents an alkyl group, an alkenyl group, an aryl group, an aralkyl group, or a heterocyclic group, which may be substituted with a halogen atom, an alkyl group, or a heterocyclic group, Among them, the alkylene part of the alkyl group and the aralkyl group may be interrupted by an unsaturated bond, an ether bond, a thioether bond, or an ester bond. R c12 and R c13 may combine to form a ring structure with the nitrogen atom.
Rc12、Rc13で示されるアルキル基としては、炭素数1〜20のものが好ましく、炭素数1〜5のものがより好ましい。アルキル基の例としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、sec−ペンチル基、tert−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、イソオクチル基、sec−オクチル基、tert−オクチル基、n−ノニル基、イソノニル基、n−デシル基、イソデシル基等の直鎖状又は分枝鎖状の基が挙げられる。また、このアルキル基は置換基を有していてもよい。置換基を有するものの例としては、メトキシエトキシエチル基、エトキシエトキシエチル基、プロピロキシエトキシエチル基、メトキシプロピル基等が挙げられる。 The alkyl group represented by R c12 and R c13 is preferably an alkyl group having 1 to 20 carbon atoms, and more preferably an alkyl group having 1 to 5 carbon atoms. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl. Group, tert-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, n-decyl group, isodecyl group And a straight chain or branched chain group such as Moreover, this alkyl group may have a substituent. Examples of those having a substituent include a methoxyethoxyethyl group, an ethoxyethoxyethyl group, a propyloxyethoxyethyl group, and a methoxypropyl group.
Rc12、Rc13で示されるアルケニル基としては、炭素数1〜20のものが好ましく、炭素数1〜5のものがより好ましい。アルケニル基の例としては、ビニル基、アリル基、ブテニル基、エテニル基、プロピニル基等の直鎖状又は分枝鎖状の基が挙げられる。また、このアルケニル基は置換基を有していてもよい。置換基を有するものの例としては、2−(ベンゾオキサゾール−2−イル)エテニル基等が挙げられる。 As the alkenyl group represented by R c12 and R c13 , those having 1 to 20 carbon atoms are preferable, and those having 1 to 5 carbon atoms are more preferable. Examples of alkenyl groups include linear or branched groups such as vinyl, allyl, butenyl, ethenyl, and propynyl groups. Moreover, this alkenyl group may have a substituent. Examples of those having a substituent include 2- (benzoxazol-2-yl) ethenyl group and the like.
Rc12、Rc13で示されるアリール基としては、炭素数6〜20のものが好ましく、炭素数6〜10のものがより好ましい。アリール基の例としては、フェニル基、トリル基、キシリル基、エチルフェニル基、ナフチル基、アントリル基、フェナントリル基等が挙げられる。 As the aryl group represented by R c12 and R c13 , those having 6 to 20 carbon atoms are preferable, and those having 6 to 10 carbon atoms are more preferable. Examples of the aryl group include phenyl group, tolyl group, xylyl group, ethylphenyl group, naphthyl group, anthryl group, phenanthryl group and the like.
Rc12、Rc13で示されるアラルキル基としては、炭素数7〜20のものが好ましく、炭素数7〜12のものがより好ましい。アラルキル基の例としては、ベンジル基、α−メチルベンジル基、α,α−ジメチルベンジル基、フェニルエチル基、フェニルエテニル基等が挙げられる。 The aralkyl group represented by R c12 and R c13 is preferably one having 7 to 20 carbon atoms, and more preferably one having 7 to 12 carbon atoms. Examples of the aralkyl group include benzyl group, α-methylbenzyl group, α, α-dimethylbenzyl group, phenylethyl group, phenylethenyl group and the like.
Rc12、Rc13で示される複素環基としては、窒素原子、硫黄原子、及び酸素原子の少なくとも1つの原子を含む5員環以上、好ましくは5〜7員環の複素環基が挙げられる。この複素環基には縮合環が含まれていてもよい。複素環基の例としては、ピロリル基、ピリジル基、ピリミジル基、フリル基、チエニル基等が挙げられる。 Examples of the heterocyclic group represented by R c12 and R c13 include 5-membered or more, preferably 5- to 7-membered heterocyclic groups containing at least one atom of a nitrogen atom, a sulfur atom, and an oxygen atom. This heterocyclic group may contain a condensed ring. Examples of the heterocyclic group include pyrrolyl, pyridyl, pyrimidyl, furyl, and thienyl groups.
これらのRc12、Rc13のうち、アルキル基及びアラルキル基のアルキレン部分は、不飽和結合、エーテル結合、チオエーテル結合、エステル結合により中断されていてもよい。 Among these R c12 and R c13 , the alkylene part of the alkyl group and the aralkyl group may be interrupted by an unsaturated bond, an ether bond, a thioether bond, or an ester bond.
また、Rc12とRc13とが結合して形成し得る環構造としては、複素環が挙げられる。この複素環としては、少なくとも窒素原子を含む5員環以上、好ましくは5〜7員環の複素環が挙げられる。この複素環には縮合環が含まれていてもよい。複素環の例としては、ピペリジン環、モルホリン環、チオモルホリン環等が挙げられる。 A ring structure that can be formed by combining R c12 and R c13 includes a heterocyclic ring. Examples of the heterocyclic ring include 5-membered or more, preferably 5 to 7-membered heterocyclic rings containing at least a nitrogen atom. This heterocyclic ring may contain a condensed ring. Examples of the heterocyclic ring include piperidine ring, morpholine ring, thiomorpholine ring and the like.
これらの中でも、Rc2としては、メチル基、エチル基、プロピル基、フェニル基であることが最も好ましい。 Among these, R c2 is most preferably a methyl group, an ethyl group, a propyl group, or a phenyl group.
上記式(C−1)中、Rc3は、一価の有機基を示す。この有機基としては、炭素数1〜5のアルキル基、置換基を有していてもよい炭素数6〜12のアリール基、下記式(C−2)で表される基、又は置換基を有していてもよい複素環基が好ましい。置換基としては、上記Rc5の場合と同様の基が挙げられる。炭素数6〜12のアリール基としては、フェニル基、ナフチル基、アントリル基、フェナントリル基等が挙げられる。
上記式(C−2)中、Rc14は、酸素原子で中断されていてもよい炭素数1〜5のアルキレン基を示す。このようなアルキレン基としては、メチレン基、エチレン基、n−プロピレン基、イソプロピレン基、n−ブチレン基、イソブチレン基、sec−ブチレン基、n−ペンチレン基、イソペンチレン基、sec−ペンチレン基等の直鎖状又は分枝鎖状の基が挙げられる。これらの中でも、Rc14はイソプロピレン基であることが最も好ましい。 In the above formula (C-2), R c14 represents an alkylene group having 1 to 5 carbon atoms which may be interrupted by an oxygen atom. Examples of such an alkylene group include methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, isobutylene group, sec-butylene group, n-pentylene group, isopentylene group, sec-pentylene group and the like. A linear or branched group is mentioned. Among these, R c14 is most preferably an isopropylene group.
上記式(C−2)中、Rc15は、−NRc16Rc17で表される一価の有機基を示す(Rc16、Rc17は、それぞれ独立に一価の有機基を示す)。そのような有機基の中でも、Rc15の構造が下記式(C−3)で表されるものであれば、光重合開始剤の溶解性を向上することができる点で好ましい。
上記式(C−3)中、Rc18、Rc19は、それぞれ独立に炭素数1〜5のアルキル基を示す。このようなアルキル基としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、sec−ペンチル基、tert−ペンチル基等が挙げられる。これらの中でも、Rc18、Rc19はメチル基であることが最も好ましい。 In said formula (C-3), R < c18 > , R <c19> shows a C1-C5 alkyl group each independently. Examples of such an alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Examples thereof include a pentyl group and a tert-pentyl group. Among these, R c18 and R c19 are most preferably methyl groups.
Rc3で示される複素環基としては、窒素原子、硫黄原子、及び酸素原子の少なくとも1つの原子を含む5員環以上、好ましくは5員環又は6員環の複素環基が挙げられる。複素環基の例としては、ピロリル基、イミダゾリル基、ピラゾリル基等の含窒素5員環基;ピリジル基、ピラジニル基、ピリミジル基、ピリダジニル基等の含窒素6員環基;チアゾリル基、イソチアゾリル基等の含窒素含硫黄基;オキサゾリル基、イソオキサゾリル基等の含窒素含酸素基;チエニル基、チオピラニル基等の含硫黄基;フリル基、ピラニル基等の含酸素基;等が挙げられる。これらの中でも、窒素原子又は硫黄原子を1つ含むものが好ましい。この複素環には縮合環が含まれていてもよい。縮合環が含まれる複素環基の例としてはベンゾチエニル基等が挙げられる。 Examples of the heterocyclic group represented by R c3 include 5-membered or more, preferably 5- or 6-membered heterocyclic groups containing at least one of a nitrogen atom, a sulfur atom, and an oxygen atom. Examples of heterocyclic groups include nitrogen-containing 5-membered ring groups such as pyrrolyl, imidazolyl and pyrazolyl groups; nitrogen-containing 6-membered ring groups such as pyridyl, pyrazinyl, pyrimidyl and pyridazinyl groups; thiazolyl and isothiazolyl groups Nitrogen-containing sulfur groups such as oxazolyl groups and isoxazolyl groups; sulfur-containing groups such as thienyl groups and thiopyranyl groups; oxygen-containing groups such as furyl groups and pyranyl groups; Among these, those containing one nitrogen atom or sulfur atom are preferable. This heterocyclic ring may contain a condensed ring. Examples of the heterocyclic group containing a condensed ring include a benzothienyl group.
また、複素環基は置換基を有していてもよい。置換基としては、上記Rc5の場合と同様の基が挙げられる。 Moreover, the heterocyclic group may have a substituent. Examples of the substituent include the same groups as in R c5 above.
上記式(C−1)中、Rc4は、一価の有機基を示す。この中でも、炭素数1〜5のアルキル基であることが好ましい。このようなアルキル基としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、sec−ペンチル基、tert−ペンチル基等が挙げられる。これらの中でも、Rc4はメチル基であることが最も好ましい。 In the above formula (C-1), R c4 represents a monovalent organic group. Among these, it is preferable that it is a C1-C5 alkyl group. Examples of such an alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec- Examples thereof include a pentyl group and a tert-pentyl group. Among these, R c4 is most preferably a methyl group.
(C)成分の含有量は、本発明に係る着色感光性樹脂組成物の固形分に対して0.1〜50質量%であることが好ましく、1〜45質量%であることがより好ましい。上記範囲内とすることにより、十分な耐熱性、耐薬品性を得るとともに、硬化不良を抑制することができる。 The content of the component (C) is preferably 0.1 to 50% by mass and more preferably 1 to 45% by mass with respect to the solid content of the colored photosensitive resin composition according to the present invention. By setting it within the above range, sufficient heat resistance and chemical resistance can be obtained, and poor curing can be suppressed.
<(D)着色剤>
(D)着色剤(以下、「(D)成分」ともいう。)としては、特に限定されず、従来公知の着色剤を用いることができる。
<(D) Colorant>
The colorant (D) (hereinafter also referred to as “component (D)”) is not particularly limited, and a conventionally known colorant can be used.
着色剤としては、例えば、カラーインデックス(C.I.;The Society of Dyers and Colourists社発行)においてピグメント(Pigment)に分類されている化合物、具体的には、下記のようなカラーインデックス(C.I.)番号が付されているものが挙げられる。 Examples of the colorant include compounds classified as pigments in the color index (CI; issued by The Society of Dyers and Colorists), specifically the following color index (C.I. I.) Numbers are given.
C.I.ピグメントイエロー1(以下、「C.I.ピグメントイエロー」は同様で番号のみ記載する。)、3、11、12、13、14、15、16、17、20、24、31、53、55、60、61、65、71、73、74、81、83、86、93、95、97、98、99、100、101、104、106、108、109、110、113、114、116、117、119、120、125、126、127、128、129、137、138、139、147、148、150、151、152、153、154、155、156、166、167、168、175、180、185;
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」は同様で番号のみ記載する。)、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」は同様で番号のみ記載する)、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」は同様で番号のみ記載する。)、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」は同様で番号のみ記載する。)、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、ピグメントブラック7。
C. I. Pigment Yellow 1 (hereinafter, “CI Pigment Yellow” is the same and only the number is described) 3, 11, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 55, 60, 61, 65, 71, 73, 74, 81, 83, 86, 93, 95, 97, 98, 99, 100, 101, 104, 106, 108, 109, 110, 113, 114, 116, 117, 119, 120, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 166, 167, 168, 175, 180, 185;
C. I. Pigment Orange 1 (hereinafter, “CI Pigment Orange” is the same, and only the number is described) 5, 13, 14, 16, 17, 24, 34, 36, 38, 40, 43, 46, 49, 51, 55, 59, 61, 63, 64, 71, 73;
C. I. Pigment Violet 1 (hereinafter, “CI Pigment Violet” is the same and only the number is described), 19, 23, 29, 30, 32, 36, 37, 38, 39, 40, 50;
C. I. Pigment Red 1 (hereinafter, “CI Pigment Red” is the same and only the number is described) 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, 79, 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. Pigment Blue 1 (hereinafter, “CI Pigment Blue” is the same and only the numbers are described), 2, 15, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, 66;
C. I. Pigment green 7, C.I. I. Pigment green 36, C.I. I. Pigment green 37;
C. I. Pigment brown 23, C.I. I. Pigment brown 25, C.I. I. Pigment brown 26, C.I. I. Pigment brown 28;
C. I. Pigment Black 1 and Pigment Black 7.
また、着色剤としては、黒色顔料を用いることが好ましい。黒色顔料としては、カーボンブラック、チタンブラック、銅、鉄、マンガン、コバルト、クロム、ニッケル、亜鉛、カルシウム、銀、錫等の金属酸化物、複合酸化物、金属硫化物、金属硫酸塩、金属合金又は金属炭酸塩等、有機物、無機物を問わず各種の顔料を挙げることができる。これらの中でも、高い遮光性を有するカーボンブラックを用いることがより好ましい。 Moreover, it is preferable to use a black pigment as a colorant. Black pigments include carbon black, titanium black, copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium, silver, tin and other metal oxides, composite oxides, metal sulfides, metal sulfates, metal alloys Or various pigments can be mentioned regardless of organic substance and inorganic substance, such as metal carbonate. Among these, it is more preferable to use carbon black having high light shielding properties.
カーボンブラックとしては、チャンネルブラック、ファーネスブラック、サーマルブラック、ランプブラック等の公知のカーボンブラックを用いることができるが、チャンネルブラックやファーネスブラックを用いることが好ましい。 As the carbon black, known carbon blacks such as channel black, furnace black, thermal black, and lamp black can be used, but channel black and furnace black are preferably used.
(D)成分の含有量は、本発明に係る着色感光性樹脂組成物の固形分に対して5〜70質量%であることが好ましく、25〜55質量%であることがより好ましく、30〜50質量%であることがさらに好ましい。 The content of the component (D) is preferably 5 to 70% by mass, more preferably 25 to 55% by mass with respect to the solid content of the colored photosensitive resin composition according to the present invention, and 30 to 30%. More preferably, it is 50 mass%.
<(S)有機溶剤>
本発明に係る着色感光性樹脂組成物は、希釈のための有機溶剤を含有することが好ましい。この有機溶剤としては、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノ−n−プロピルエーテル、ジエチレングリコールモノ−n−ブチルエーテル、トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノ−n−プロピルエーテル、プロピレングリコールモノ−n−ブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノ−n−プロピルエーテル、ジプロピレングリコールモノ−n−ブチルエーテル、トリプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノエチルエーテル等の(ポリ)アルキレングリコールモノアルキルエーテル類;エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート等の(ポリ)アルキレングリコールモノアルキルエーテルアセテート類;ジエチレングリコールジメチルエーテル、ジエチレングリコールメチルエチルエーテル、ジエチレングリコールジエチルエーテル、テトラヒドロフラン等の他のエーテル類;メチルエチルケトン、シクロヘキサノン、2−ヘプタノン、3−ヘプタノン等のケトン類;2−ヒドロキシプロピオン酸メチル、2−ヒドロキシプロピオン酸エチル等の乳酸アルキルエステル類;2−ヒドロキシ−2−メチルプロピオン酸エチル、3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−エトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、エトキシ酢酸エチル、ヒドロキシ酢酸エチル、2−ヒドロキシ−3−メチルブタン酸メチル、3−メチル−3−メトキシブチルアセテート、3−メチル−3−メトキシブチルプロピオネート、酢酸エチル、酢酸n−プロピル、酢酸イソプロピル、酢酸n−ブチル、酢酸イソブチル、ぎ酸n−ペンチル、酢酸イソペンチル、プロピオン酸n−ブチル、酪酸エチル、酪酸n−プロピル、酪酸イソプロピル、酪酸n−ブチル、ピルビン酸メチル、ピルビン酸エチル、ピルビン酸n−プロピル、アセト酢酸メチル、アセト酢酸エチル、2−オキソブタン酸エチル等の他のエステル類;トルエン、キシレン等の芳香族炭化水素類;N−メチルピロリドン、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド等のアミド類等が挙げられる。これらの有機溶剤は、単独又は2種以上組み合わせて用いることができる。
<(S) Organic solvent>
The colored photosensitive resin composition according to the present invention preferably contains an organic solvent for dilution. Examples of the organic solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether. , Diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, di Propylene glycol monomethyl ether, zip (Poly) alkylene glycol monoalkyl ethers such as pyrene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether; ethylene (Poly) alkylene glycol monoalkyl ether acetates such as glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate; diethylene glycol dimethyl Other ethers such as ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether and tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone and 3-heptanone; methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, etc. Lactic acid alkyl esters; ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, hydroxyacetic acid Ethyl, methyl 2-hydroxy-3-methylbutanoate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutylpropionate, ethyl acetate, n-acetate -Propyl, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, methyl pyruvate, pyruvin Other esters such as ethyl acetate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate and ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; N-methylpyrrolidone, N, N-dimethyl Examples include amides such as formamide and N, N-dimethylacetamide. These organic solvents can be used alone or in combination of two or more.
これらの中でも、プロピレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、ジエチレングリコールジメチルエーテル、ジエチレングリコールメチルエチルエーテル、シクロヘキサノン、3−メトキシブチルアセテートは、(A)成分、(B)成分、(C)成分に対して優れた溶解性を示すとともに、黒色顔料等の不溶性成分の分散性を良好にすることができるため好ましい。 Among these, propylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, and 3-methoxybutyl acetate are (A) component, It is preferable because it exhibits excellent solubility in the component (B) and the component (C) and can improve the dispersibility of insoluble components such as black pigments.
(S)成分の含有量は、本発明に係る着色感光性樹脂組成物の固形分濃度が5〜30質量%となる量が好ましい。 The content of the component (S) is preferably such that the solid content concentration of the colored photosensitive resin composition according to the present invention is 5 to 30% by mass.
<その他の成分>
本発明に係る着色感光性樹脂組成物は、必要に応じて添加剤を含有してもよい。添加剤としては、増感剤、硬化促進剤、架橋剤、分散助剤、充填剤、密着促進剤、酸化防止剤、紫外線吸収剤、凝集防止剤、熱重合禁止剤、消泡剤、界面活性剤等が挙げられる。
<Other ingredients>
The colored photosensitive resin composition according to the present invention may contain an additive as necessary. Additives include sensitizers, curing accelerators, crosslinking agents, dispersion aids, fillers, adhesion promoters, antioxidants, UV absorbers, anti-aggregation agents, thermal polymerization inhibitors, antifoaming agents, and surface active agents. Agents and the like.
<着色感光性樹脂組成物の調製方法>
本発明に係る着色感光性樹脂組成物は、上記各成分を全て撹拌機で混合することにより得られる。なお、得られた組成物が均一なものとなるよう、メンブランフィルタを用いて濾過してもよい。
<Preparation method of colored photosensitive resin composition>
The colored photosensitive resin composition according to the present invention can be obtained by mixing all the above components with a stirrer. In addition, you may filter using a membrane filter so that the obtained composition may become uniform.
≪タッチパネル及び表示装置≫
本発明に係るタッチパネルは、本発明に係る着色感光性樹脂組成物を用いて形成された硬化樹脂パターンを有するものである。また、本発明に係る表示装置は、本発明に係るタッチパネルを備えたものである。
≪Touch panel and display device≫
The touch panel according to the present invention has a cured resin pattern formed using the colored photosensitive resin composition according to the present invention. The display device according to the present invention includes the touch panel according to the present invention.
タッチパネルに硬化樹脂パターンを形成するには、まず、ロールコータ、リバースコータ、バーコータ等の接触転写型塗布装置やスピンナー(回転式塗布装置)、カーテンフローコータ等の非接触型塗布装置を用いて、基板上に本発明に係る着色感光性樹脂組成物を塗布する。 In order to form a cured resin pattern on the touch panel, first, a contact transfer type coating device such as a roll coater, reverse coater, bar coater or the like, a spinner (rotary coating device), a non-contact type coating device such as a curtain flow coater, The colored photosensitive resin composition according to the present invention is applied on a substrate.
次いで、塗布された着色感光性樹脂組成物を乾燥させて塗膜を形成する。乾燥方法は特に限定されず、例えば(1)ホットプレートにて80〜120℃、好ましくは90〜100℃の温度にて60〜120秒間乾燥する方法、(2)室温にて数時間〜数日放置する方法、(3)温風ヒータや赤外線ヒータ中に数十分〜数時間入れて溶剤を除去する方法、のいずれの方法を用いてもよい。 Next, the applied colored photosensitive resin composition is dried to form a coating film. The drying method is not particularly limited. For example, (1) a method of drying on a hot plate at 80 to 120 ° C., preferably 90 to 100 ° C. for 60 to 120 seconds, and (2) room temperature for several hours to several days. Any of a method of leaving it, and a method of removing the solvent by putting it in a warm air heater or an infrared heater for several tens of minutes to several hours may be used.
次いで、この塗膜に、ネガ型のマスクを介して紫外線、エキシマレーザー光等の活性エネルギー線を照射して部分的に露光する。照射するエネルギー線量は、着色感光性樹脂組成物の組成によっても異なるが、例えば20〜200mJ/cm2程度が好ましい。 Next, this coating film is partially exposed by irradiating active energy rays such as ultraviolet rays and excimer laser light through a negative mask. The energy dose to be irradiated varies depending on the composition of the colored photosensitive resin composition, but is preferably about 20 to 200 mJ / cm 2 , for example.
次いで、露光後の塗膜を、現像液により現像することによって所望の形状にパターニングする。現像方法は特に限定されず、浸漬法、スプレー法等を用いることができる。現像液としては、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン等の有機系のものや、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、アンモニア、4級アンモニウム塩等の水溶液が挙げられる。 Next, the exposed coating film is developed into a desired shape by developing with a developer. The development method is not particularly limited, and an immersion method, a spray method, or the like can be used. Examples of the developer include organic ones such as monoethanolamine, diethanolamine, and triethanolamine, and aqueous solutions such as sodium hydroxide, potassium hydroxide, sodium carbonate, ammonia, and quaternary ammonium salts.
次いで、現像後のパターンに対して200〜250℃程度でポストベークを行う。この際、形成されたパターンを全面露光することが好ましい。 Next, post-baking is performed on the developed pattern at about 200 to 250 ° C. At this time, it is preferable to expose the entire surface of the formed pattern.
上記のように部分露光及び現像によって硬化樹脂パターンを形成する方法の他に、例えば、インクジェットプリンタを使用して硬化樹脂パターンを形成してもよい。この場合、基板上に本発明に係る着色感光性樹脂組成物を所望のパターン形状となるように吐出させ、次いで、乾燥、露光、及びポストベークを経て硬化樹脂パターンを形成する。 In addition to the method of forming the cured resin pattern by partial exposure and development as described above, the cured resin pattern may be formed using, for example, an ink jet printer. In this case, the colored photosensitive resin composition according to the present invention is discharged onto the substrate so as to have a desired pattern shape, and then a cured resin pattern is formed through drying, exposure, and post-baking.
上記のようにして硬化樹脂パターンが形成されたタッチパネルを定法に従って表示装置に組み込むことにより、本発明に係る表示装置を製造することができる。 The display device according to the present invention can be manufactured by incorporating the touch panel on which the cured resin pattern is formed as described above into the display device according to a conventional method.
以下、本発明の実施例を説明するが、本発明の範囲はこれらの実施例に限定されるものではない。なお、以下の記載において「部」、「%」はそれぞれ質量基準である。 Examples of the present invention will be described below, but the scope of the present invention is not limited to these examples. In the following description, “parts” and “%” are based on mass.
<合成例1>
まず、500ml四つ口フラスコ中に、ビスフェノールフルオレン型エポキシ樹脂(エポキシ当量235)235g、テトラメチルアンモニウムクロライド110mg、2,6−ジ−tert−ブチル−4−メチルフェノール100mg、及びアクリル酸72.0gを仕込み、これに25ml/分の速度で空気を吹き込みながら90〜100℃で加熱溶解した。次に、溶液が白濁した状態のまま徐々に昇温し、120℃に加熱して完全溶解させた。この際、溶液は次第に透明粘稠になったが、そのまま撹拌を継続した。この間、酸価を測定し、1.0mgKOH/g未満になるまで加熱撹拌を続けた。酸価が目標値に達するまで12時間を要した。そして室温まで冷却し、無色透明で固体状の下記式(A−10)で表されるビスフェノールフルオレン型エポキシアクリレートを得た。
First, in a 500 ml four-necked flask, 235 g of bisphenolfluorene type epoxy resin (epoxy equivalent 235), 110 mg of tetramethylammonium chloride, 100 mg of 2,6-di-tert-butyl-4-methylphenol, and 72.0 g of acrylic acid Was heated and dissolved at 90 to 100 ° C. while blowing air at a rate of 25 ml / min. Next, the temperature was gradually raised while the solution was clouded, and the solution was heated to 120 ° C. to be completely dissolved. At this time, the solution gradually became transparent and viscous, but stirring was continued as it was. During this time, the acid value was measured, and heating and stirring were continued until the acid value was less than 1.0 mgKOH / g. It took 12 hours for the acid value to reach the target value. And it cooled to room temperature and obtained the bisphenol fluorene type epoxy acrylate represented by the following formula (A-10) which is colorless and transparent and solid.
次いで、このようにして得られた上記のビスフェノールフルオレン型エポキシアクリレート307.0gに3−メトキシブチルアセテート600gを加えて溶解した後、ベンゾフェノンテトラカルボン酸二無水物80.5g及び臭化テトラエチルアンモニウム1gを混合し、徐々に昇温して110〜115℃で4時間反応させた。酸無水物基の消失を確認した後、1,2,3,6−テトラヒドロ無水フタル酸38.0gを混合し、90℃で6時間反応させ、樹脂A1を得た。酸無水物基の消失はIRスペクトルにより確認した。
この樹脂A1は、上記式(A−7)で表される化合物に相当する。
Next, after adding 600 g of 3-methoxybutyl acetate to 307.0 g of the bisphenolfluorene type epoxy acrylate thus obtained and dissolving, 80.5 g of benzophenonetetracarboxylic dianhydride and 1 g of tetraethylammonium bromide were added. The mixture was gradually heated and reacted at 110 to 115 ° C. for 4 hours. After confirming the disappearance of the acid anhydride group, 38.0 g of 1,2,3,6-tetrahydrophthalic anhydride was mixed and reacted at 90 ° C. for 6 hours to obtain Resin A1. The disappearance of the acid anhydride group was confirmed by IR spectrum.
This resin A1 corresponds to the compound represented by the above formula (A-7).
<実施例1>
下記に示す各成分を固形分濃度15質量%となるように、3−メトキシブチルアセテート/シクロヘキサノン/プロピレングリコールモノメチルエーテルアセテート=60/20/20(質量比)の混合溶剤に溶解し、撹拌機で2時間混合した後、孔径5μmのメンブランフィルタで濾過し、着色感光性樹脂組成物を調製した。
・バインダー化合物
合成例1で得られた樹脂A1・・・95部
スチレン/メタクリル酸=80/20(質量比)の共重合体(樹脂A2、質量平均分子量13000)・・・60部
「EHPE3150」(ダイセル化学工業社製;2,2−ビス(ヒドロキシメチル)−1−ブタノールの1,2−エポキシ−4−(2−オキシラニル)シクロヘキサン付加物;下記式(1)参照)・・・155部
・光重合性モノマー
ジペンタエリスリトールヘキサアクリレート(日本化薬社製)・・・175部
・光重合開始剤
「OXE−02」(BASF社製;エタノン−1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル]−1−(O−アセチルオキシム))・・・100部
・着色剤
カーボンブラック(御国色素社製)・・・450部
<Example 1>
Each component shown below was dissolved in a mixed solvent of 3-methoxybutyl acetate / cyclohexanone / propylene glycol monomethyl ether acetate = 60/20/20 (mass ratio) so as to have a solid content concentration of 15% by mass. After mixing for 2 hours, the mixture was filtered through a membrane filter having a pore size of 5 μm to prepare a colored photosensitive resin composition.
-Binder compound Resin A1 obtained in Synthesis Example 1 95 parts Copolymer of styrene / methacrylic acid = 80/20 (mass ratio) (resin A2, mass average molecular weight 13000) ... 60 parts "EHPE3150" (Daicel Chemical Industries, Ltd .; 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol; see formula (1) below) 155 parts Photopolymerizable monomer Dipentaerythritol hexaacrylate (Nippon Kayaku Co., Ltd.) 175 parts Photopolymerization initiator “OXE-02” (manufactured by BASF; Etanone-1- [9-ethyl-6- (2 -Methylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime)) ... 100 parts Colorant Carbon black (manufactured by Mikuni Dye Company) 450 parts
<実施例2〜5>
バインダー化合物の組成を表1のように変更し、バインダー化合物の全量に対するエポキシ化合物の割合を40%、30%、20%、10%としたほかは、実施例1と同様にして着色感光性樹脂組成物を調製した。なお、表1中の数値は質量部を表す。
<Examples 2 to 5>
The colored photosensitive resin is the same as in Example 1 except that the composition of the binder compound is changed as shown in Table 1 and the ratio of the epoxy compound to the total amount of the binder compound is 40%, 30%, 20%, and 10%. A composition was prepared. In addition, the numerical value in Table 1 represents a mass part.
<実施例6>
表1に示すように、「EHPE3150」の代わりに下記式(2)で表される「セロキサイド2021P」(ダイセル化学工業社製)を用いたほかは、実施例1と同様にして着色感光性樹脂組成物を調製した。
<Example 6>
As shown in Table 1, a colored photosensitive resin was used in the same manner as in Example 1 except that “Celoxide 2021P” (manufactured by Daicel Chemical Industries) represented by the following formula (2) was used instead of “EHPE3150”. A composition was prepared.
<実施例7〜10>
バインダー化合物の組成を表1のように変更し、バインダー化合物の全量に対するエポキシ化合物の割合を40%、30%、20%、10%としたほかは、実施例6と同様にして着色感光性樹脂組成物を調製した。なお、表1中の数値は質量部を表す。
<Examples 7 to 10>
The colored photosensitive resin is the same as in Example 6 except that the composition of the binder compound is changed as shown in Table 1 and the ratio of the epoxy compound to the total amount of the binder compound is 40%, 30%, 20%, and 10%. A composition was prepared. In addition, the numerical value in Table 1 represents a mass part.
<実施例11>
表1に示すように、「EHPE3150」の代わりに下記式(3)で表される「セロキサイド2081」(ダイセル化学工業社製)を用いたほかは、実施例1と同様にして着色感光性樹脂組成物を調製した。
<Example 11>
As shown in Table 1, a colored photosensitive resin was used in the same manner as in Example 1 except that “Celoxide 2081” (manufactured by Daicel Chemical Industries, Ltd.) represented by the following formula (3) was used instead of “EHPE3150”. A composition was prepared.
<実施例12〜15>
バインダー化合物の組成を表1のように変更し、バインダー化合物の全量に対するエポキシ化合物の割合を40%、30%、20%、10%としたほかは、実施例11と同様にして着色感光性樹脂組成物を調製した。なお、表1中の数値は質量部を表す。
<Examples 12 to 15>
Colored photosensitive resin in the same manner as in Example 11 except that the composition of the binder compound was changed as shown in Table 1, and the ratio of the epoxy compound to the total amount of the binder compound was 40%, 30%, 20%, and 10%. A composition was prepared. In addition, the numerical value in Table 1 represents a mass part.
<実施例16>
表2に示すように、「EHPE3150」の代わりに下記式(4)で表される「セロキサイド2000」(ダイセル化学工業社製)を用いたほかは、実施例1と同様にして着色感光性樹脂組成物を調製した。
<Example 16>
As shown in Table 2, a colored photosensitive resin was used in the same manner as in Example 1 except that “Celoxide 2000” (manufactured by Daicel Chemical Industries) represented by the following formula (4) was used instead of “EHPE3150”. A composition was prepared.
<実施例17〜20>
バインダー化合物の組成を表2のように変更し、バインダー化合物の全量に対するエポキシ化合物の割合を40%、30%、20%、10%としたほかは、実施例16と同様にして着色感光性樹脂組成物を調製した。なお、表2中の数値は質量部を表す。
<Examples 17 to 20>
Colored photosensitive resin in the same manner as in Example 16 except that the composition of the binder compound was changed as shown in Table 2 and the ratio of the epoxy compound to the total amount of the binder compound was 40%, 30%, 20% and 10%. A composition was prepared. In addition, the numerical value in Table 2 represents a mass part.
<実施例21>
表2に示すように、「EHPE3150」の代わりに下記式(5)で表される「セロキサイド3000」(ダイセル化学工業社製)を用いたほかは、実施例1と同様にして着色感光性樹脂組成物を調製した。
<Example 21>
As shown in Table 2, a colored photosensitive resin was used in the same manner as in Example 1 except that “Celoxide 3000” (manufactured by Daicel Chemical Industries, Ltd.) represented by the following formula (5) was used instead of “EHPE3150”. A composition was prepared.
<実施例22〜25>
バインダー化合物の組成を表2のように変更し、バインダー化合物の全量に対するエポキシ化合物の割合を40%、30%、20%、10%としたほかは、実施例21と同様にして着色感光性樹脂組成物を調製した。なお、表2中の数値は質量部を表す。
<Examples 22 to 25>
Colored photosensitive resin in the same manner as in Example 21 except that the composition of the binder compound was changed as shown in Table 2 and the ratio of the epoxy compound to the total amount of the binder compound was 40%, 30%, 20% and 10%. A composition was prepared. In addition, the numerical value in Table 2 represents a mass part.
<比較例1>
バインダー化合物の組成を表2のように変更し、バインダー化合物中にエポキシ化合物を含めなかったほかは、実施例1と同様にして着色感光性樹脂組成物を調製した。なお、表2中の数値は質量部を表す。
<Comparative Example 1>
A colored photosensitive resin composition was prepared in the same manner as in Example 1 except that the composition of the binder compound was changed as shown in Table 2 and the epoxy compound was not included in the binder compound. In addition, the numerical value in Table 2 represents a mass part.
<評価>
[耐薬品性の評価]
実施例1〜25、比較例1で調製した着色感光性樹脂組成物を、スピンコーター(TR25000:東京応化工業社製)を用いてガラス基板(Corning社製、E2Kガラス)上に塗布し、90℃で120秒間乾燥して膜厚1.8μmの塗膜を形成した。次いで、この塗膜に、ミラープロジェクションアライナー(TME−150RTO:トプコン社製)を用いて紫外線(波長365nm、照射量50mJ)を照射した。そして、230℃で20分間、循環式オーブンにてポストベークを行い、硬化膜を得た。
この硬化膜が形成されたガラス基板を40℃のエッチング液(H3PO4/CH3COOH/HNO3/H2O=65/3/12/22)に1分間浸漬し、水洗した後、エアーブローによる水切りを行った。さらに、硬化膜が形成されたガラス基板を60℃の剥離液(DMSO/モノエタノールアミン=30/70)に1分間浸漬し、水洗した後、エアーブローによる水切りを行った。
その後、硬化膜の耐薬品性を評価するため、クロスハッチテストを行った。具体的には、ISO2409(ASTM D−3359)に準拠し、硬化膜を2.0mmの間隔で100目クロスカット(縦横11カットずつ)し、このクロスカットした箇所に、粘着テープを強く貼り付けた後、粘着テープを急速に剥がして硬化膜の剥離の有無を調べ、クラス0Bからクラス5Bまでの6段階で評価した。結果を下記表1,2に示す。
<Evaluation>
[Evaluation of chemical resistance]
The colored photosensitive resin compositions prepared in Examples 1 to 25 and Comparative Example 1 were applied onto a glass substrate (Corning, E2K glass) using a spin coater (TR25000: manufactured by Tokyo Ohka Kogyo Co., Ltd.), 90 The coating film was dried at 120 ° C. for 120 seconds to form a coating film having a thickness of 1.8 μm. Subsequently, this coating film was irradiated with ultraviolet rays (wavelength 365 nm, irradiation amount 50 mJ) using a mirror projection aligner (TME-150 RTO: manufactured by Topcon Corporation). Then, post-baking was performed in a circulation oven at 230 ° C. for 20 minutes to obtain a cured film.
The glass substrate on which this cured film was formed was immersed for 1 minute in an etching solution at 40 ° C. (H 3 PO 4 / CH 3 COOH / HNO 3 / H 2 O = 65/3/12/22), washed with water, Drained by air blow. Furthermore, the glass substrate on which the cured film was formed was immersed in a stripping solution (DMSO / monoethanolamine = 30/70) at 60 ° C. for 1 minute, washed with water, and then drained by air blow.
Thereafter, a cross-hatch test was performed to evaluate the chemical resistance of the cured film. Specifically, in conformity with ISO 2409 (ASTM D-3359), the cured film is cross-cut at 100 stitches at intervals of 2.0 mm (11 cuts in length and width), and the adhesive tape is firmly attached to the cross-cut portions. After that, the adhesive tape was peeled off rapidly to examine the presence or absence of peeling of the cured film, and the evaluation was made in 6 stages from class 0B to class 5B. The results are shown in Tables 1 and 2 below.
[耐候性の評価]
実施例1〜25、比較例1で調製した着色感光性樹脂組成物を用いて、上記[耐薬品性の評価]と同様にしてガラス基板上に硬化膜を形成した。
この硬化膜に対して、ウェザーメーター(Xenon X75:スガ試験機社製)を用いて耐候性試験を実施した。具体的には、温度60℃、湿度100%RH、UV有りの照射試験1回と、温度50℃、湿度100%RH、UV無しの暗黒試験1回とを1サイクル(8時間)とし、これを25サイクル(200時間)行った。
その後、硬化膜の耐候性を評価するため、上記[耐薬品性の評価]と同様にしてクロスハッチテストを行った。結果を下記表1,2に示す。
[Evaluation of weather resistance]
Using the colored photosensitive resin compositions prepared in Examples 1 to 25 and Comparative Example 1, a cured film was formed on a glass substrate in the same manner as in the above [Evaluation of chemical resistance].
A weather resistance test was performed on the cured film using a weather meter (Xenon X75: manufactured by Suga Test Instruments Co., Ltd.). More specifically, one irradiation test with a temperature of 60 ° C., humidity of 100% RH and UV and one dark test without a temperature of 50 ° C., humidity of 100% RH and UV are defined as one cycle (8 hours). For 25 cycles (200 hours).
Thereafter, in order to evaluate the weather resistance of the cured film, a cross hatch test was performed in the same manner as in the above [Evaluation of chemical resistance]. The results are shown in Tables 1 and 2 below.
表1,2から分かるように、バインダー化合物としてエポキシ化合物を含有する実施例1〜25の着色感光性樹脂組成物を用いた場合には、耐薬品性試験後のクロスハッチテスト及び耐候性試験後のクロスハッチテストの双方において、クラス0B以上の密着性を示した。その中でも、バインダー化合物の全量に対するエポキシ化合物の割合が40〜50%の場合には、耐薬品性試験後のクロスハッチテストにおいてクラス5B、耐候性試験後のクロスハッチテストにおいてクラス3B以上の密着性を示し、特にエポキシ化合物としてEHPE3150を用いた実施例1,2では、耐薬品性試験後のクロスハッチテスト及び耐候性試験後のクロスハッチテストの双方において、クラス5Bの密着性を示した。 As can be seen from Tables 1 and 2, when the colored photosensitive resin compositions of Examples 1 to 25 containing an epoxy compound as a binder compound were used, after the cross-hatch test and the weather resistance test after the chemical resistance test In both of the cross-hatch tests, adhesion of class 0B or higher was shown. Among them, when the ratio of the epoxy compound to the total amount of the binder compound is 40 to 50%, the adhesion is Class 5B in the cross hatch test after the chemical resistance test, and Class 3B or higher in the cross hatch test after the weather resistance test. In particular, in Examples 1 and 2 using EHPE3150 as an epoxy compound, the adhesion of class 5B was shown in both the cross hatch test after the chemical resistance test and the cross hatch test after the weather resistance test.
これに対して、バインダー化合物としてエポキシ化合物を含有しない比較例1の着色感光性樹脂組成物を用いた場合には、耐候性試験後のクロスハッチテストにおいてクラス0Bの密着性を示したものの、耐薬品性に著しく劣るため、エッチング処理中又は剥離処理中に塗膜が剥離してしまい、耐薬品性試験後のクロスハッチテストの実施まで至らなかった。 On the other hand, when the colored photosensitive resin composition of Comparative Example 1 containing no epoxy compound was used as the binder compound, it exhibited class 0B adhesion in the cross-hatch test after the weather resistance test, Since the chemical property is remarkably inferior, the coating film was peeled off during the etching treatment or the peeling treatment, and the cross-hatch test after the chemical resistance test was not conducted.
Claims (4)
前記(A)バインダー化合物が下記式(A−1)で表されるエポキシ化合物及び下記式(A−7)で表される化合物を含み、
前記エポキシ化合物の割合が、前記(A)バインダー化合物の全量に対して40〜60質量%である、タッチパネル用着色感光性樹脂組成物。
The look-containing compound represented by the binder (A) compound following epoxy compound represented by (A-1) and the following formula (A-7),
The coloring photosensitive resin composition for touchscreens whose ratio of the said epoxy compound is 40-60 mass% with respect to the whole quantity of the said (A) binder compound .
A display device comprising the touch panel according to claim 3 .
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011003136A JP5744528B2 (en) | 2011-01-11 | 2011-01-11 | Colored photosensitive resin composition for touch panel, touch panel, and display device |
TW100148673A TWI578104B (en) | 2011-01-11 | 2011-12-26 | The touch panel is colored with a photosensitive resin composition, a touch panel and a display device |
KR1020120001366A KR101840055B1 (en) | 2011-01-11 | 2012-01-05 | Colored photosensitive resin composition for touch panel, touch panel and display device |
CN201210005343.8A CN102591148B (en) | 2011-01-11 | 2012-01-09 | For the photosensitive composition of contact panel and contact panel and display device |
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KR102162595B1 (en) * | 2013-03-21 | 2020-10-07 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | Photosensitive resin composition for insulation layer, and cured product thereof |
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TW200519535A (en) * | 2003-11-27 | 2005-06-16 | Taiyo Ink Mfg Co Ltd | Hardenable resin composition, hardened body thereof, and printed circuit board |
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JP4809006B2 (en) * | 2005-07-05 | 2011-11-02 | 太陽ホールディングス株式会社 | Colored photosensitive resin composition and cured product thereof |
JP4745110B2 (en) * | 2006-04-19 | 2011-08-10 | 東京応化工業株式会社 | Photosensitive composition and color filter formed with the photosensitive composition |
JP4949809B2 (en) * | 2006-11-14 | 2012-06-13 | 東京応化工業株式会社 | Colored photosensitive resin composition |
JP5535692B2 (en) * | 2009-03-17 | 2014-07-02 | 富士フイルム株式会社 | Colored curable composition, color filter, and method for producing color filter |
JP2011227467A (en) * | 2010-03-31 | 2011-11-10 | Toray Ind Inc | Photosensitive black resin composition and resin black matrix substrate |
JP2012078528A (en) * | 2010-09-30 | 2012-04-19 | Fujifilm Corp | Photosensitive composition, photosensitive resin transfer film, resin pattern and production method of resin pattern, substrate for liquid crystal display device, and liquid crystal display device |
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2011
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- 2011-12-26 TW TW100148673A patent/TWI578104B/en active
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CN102591148A (en) | 2012-07-18 |
JP2012145699A (en) | 2012-08-02 |
TWI578104B (en) | 2017-04-11 |
CN102591148B (en) | 2016-12-14 |
TW201232176A (en) | 2012-08-01 |
KR101840055B1 (en) | 2018-03-19 |
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