CN112625479A - Thermosetting composition, cured film and color filter - Google Patents
Thermosetting composition, cured film and color filter Download PDFInfo
- Publication number
- CN112625479A CN112625479A CN202011038531.1A CN202011038531A CN112625479A CN 112625479 A CN112625479 A CN 112625479A CN 202011038531 A CN202011038531 A CN 202011038531A CN 112625479 A CN112625479 A CN 112625479A
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- Prior art keywords
- compound
- acid
- weight
- thermosetting composition
- parts
- Prior art date
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- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 98
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- -1 acrylamide compound Chemical class 0.000 claims abstract description 114
- 239000002253 acid Substances 0.000 claims abstract description 74
- 239000004593 Epoxy Substances 0.000 claims abstract description 69
- 229920000728 polyester Polymers 0.000 claims abstract description 36
- 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 abstract description 34
- 150000004985 diamines Chemical class 0.000 claims abstract description 23
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims abstract description 22
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 230000001681 protective effect Effects 0.000 claims description 16
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 4
- 239000010408 film Substances 0.000 description 94
- 239000000047 product Substances 0.000 description 60
- 239000002904 solvent Substances 0.000 description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 34
- 239000003795 chemical substances by application Substances 0.000 description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 27
- 239000000758 substrate Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 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 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000003860 storage Methods 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 12
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 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 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 8
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 8
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 8
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- 239000000600 sorbitol Substances 0.000 description 8
- 230000004580 weight loss Effects 0.000 description 8
- 125000004018 acid anhydride group Chemical group 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- SBVKVAIECGDBTC-UHFFFAOYSA-N 4-hydroxy-2-methylidenebutanamide Chemical compound NC(=O)C(=C)CCO SBVKVAIECGDBTC-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 125000005395 methacrylic acid group Chemical group 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 6
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 5
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 5
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 5
- UVRCNEIYXSRHNT-UHFFFAOYSA-N 3-ethylpent-2-enamide Chemical compound CCC(CC)=CC(N)=O UVRCNEIYXSRHNT-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- UTSYWKJYFPPRAP-UHFFFAOYSA-N n-(butoxymethyl)prop-2-enamide Chemical compound CCCCOCNC(=O)C=C UTSYWKJYFPPRAP-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- FVCHRIQAIOHAIC-UHFFFAOYSA-N 2-[1-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COC(C)COCC1CO1 FVCHRIQAIOHAIC-UHFFFAOYSA-N 0.000 description 4
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 4
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 4
- 229920001214 Polysorbate 60 Polymers 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-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
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- KCTMTGOHHMRJHZ-UHFFFAOYSA-N n-(2-methylpropoxymethyl)prop-2-enamide Chemical compound CC(C)COCNC(=O)C=C KCTMTGOHHMRJHZ-UHFFFAOYSA-N 0.000 description 4
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- 229940043375 1,5-pentanediol Drugs 0.000 description 3
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 3
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 3
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 3
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- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 229960003237 betaine Drugs 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 3
- 229940051841 polyoxyethylene ether Drugs 0.000 description 3
- 229920000056 polyoxyethylene ether Polymers 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 description 2
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- OLQWMCSSZKNOLQ-ZXZARUISSA-N (3s)-3-[(3r)-2,5-dioxooxolan-3-yl]oxolane-2,5-dione Chemical compound O=C1OC(=O)C[C@H]1[C@@H]1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-ZXZARUISSA-N 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
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- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- ZITKDVFRMRXIJQ-UHFFFAOYSA-N dodecane-1,2-diol Chemical compound CCCCCCCCCCC(O)CO ZITKDVFRMRXIJQ-UHFFFAOYSA-N 0.000 description 1
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- 238000004070 electrodeposition Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
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- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- AKWHOGIYEOZALP-UHFFFAOYSA-N methyl 2-methoxy-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC AKWHOGIYEOZALP-UHFFFAOYSA-N 0.000 description 1
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- 229940017219 methyl propionate Drugs 0.000 description 1
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- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- YRDNVESFWXDNSI-UHFFFAOYSA-N n-(2,4,4-trimethylpentan-2-yl)prop-2-enamide Chemical compound CC(C)(C)CC(C)(C)NC(=O)C=C YRDNVESFWXDNSI-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 description 1
- XQPVIMDDIXCFFS-UHFFFAOYSA-N n-dodecylprop-2-enamide Chemical compound CCCCCCCCCCCCNC(=O)C=C XQPVIMDDIXCFFS-UHFFFAOYSA-N 0.000 description 1
- BPCNEKWROYSOLT-UHFFFAOYSA-N n-phenylprop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC=C1 BPCNEKWROYSOLT-UHFFFAOYSA-N 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- CUUVVDHSUIKLPH-UHFFFAOYSA-N nonane-1,2,9-triol Chemical compound OCCCCCCCC(O)CO CUUVVDHSUIKLPH-UHFFFAOYSA-N 0.000 description 1
- LJZULWUXNKDPCG-UHFFFAOYSA-N nonane-1,2-diol Chemical compound CCCCCCCC(O)CO LJZULWUXNKDPCG-UHFFFAOYSA-N 0.000 description 1
- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- GKCGJDQACNSNBB-UHFFFAOYSA-N octane-1,2,8-triol Chemical compound OCCCCCCC(O)CO GKCGJDQACNSNBB-UHFFFAOYSA-N 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
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- BCKOQWWRTRBSGR-UHFFFAOYSA-N octane-3,6-diol Chemical compound CCC(O)CCC(O)CC BCKOQWWRTRBSGR-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WEAYWASEBDOLRG-UHFFFAOYSA-N pentane-1,2,5-triol Chemical compound OCCCC(O)CO WEAYWASEBDOLRG-UHFFFAOYSA-N 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- NMWCXUDFZWVKKJ-UHFFFAOYSA-N propan-2-yl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC(C)C NMWCXUDFZWVKKJ-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 235000008001 rakum palm Nutrition 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- 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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Optical Filters (AREA)
- Epoxy Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The problem of the present invention is to provide a thermosetting composition capable of providing a cured film having excellent flatness, and a cured film and a color filter formed from the thermosetting composition. The invention provides an electronic part with the hardening film. A thermosetting composition comprising a polyester amic acid (A), an epoxy compound (B), a compound (C) having a polymerizable double bond, and a monofunctional acrylamide compound (D), wherein the polyester amic acid (A) is a reaction product of raw materials comprising X moles of a tetracarboxylic dianhydride, Y moles of a diamine, and Z moles of a polyhydric hydroxyl compound at a ratio satisfying the relationship between the following formulae (1) and (2). 0.2 ≦ Z/Y ≦ 8.0 … … (1)0.2 ≦ (Y + Z)/X ≦ 5.0 … … (2).
Description
Technical Field
The present invention relates to a thermosetting composition, and a cured film and a color filter formed from the thermosetting composition. The present invention also relates to an electronic material such as an insulating film, a passivation film, a buffer coating film, a planarization film, or a protective film for a color filter (color filter) formed using the composition. Further, the present invention relates to an electronic component using the material. The present invention also relates to an electrical product such as a semiconductor device or a liquid crystal display device using the above component.
Background
In a process for manufacturing an element such as a liquid crystal display element, the element may be subjected to a chemical treatment using an organic solvent or the like, or a heating treatment when a wiring electrode is formed by sputtering or the like. Therefore, a surface protective film is sometimes provided for the purpose of preventing the surface of each element from being deteriorated, damaged, or deteriorated. These protective films are required to withstand the treatment in the manufacturing process described above. Specifically, it is required to have heat resistance, chemical resistance such as solvent resistance, water resistance, adhesion to a base substrate such as glass, transparency, scratch resistance, flatness, light resistance, and the like. In addition, the thermosetting composition is required to have good coatability when forming the front protective film.
Further, in recent years, the manufacturing base of liquid crystal display devices is advancing overseas transportation or overseas new installation, the period of conveying the thermosetting material is further prolonged than before, and excellent storage stability such as no change in viscosity is observed even when the thermosetting material is stored for a long period of time is also required.
In the process of improving heat resistance required for display element members as required characteristics for reliability required for display elements are improved, a thermosetting composition containing a polyester amic acid and an epoxy compound having good heat resistance has been proposed (patent document 1). Further, in recent years, due to the upsizing of the production line, for example, in order to reduce the in-plane unevenness of the alignment film at the time of rubbing, it is necessary to press the rubbing roll more strongly than before, and therefore, it is required to improve the scratch resistance of the protective film. On the other hand, it has been proposed that a thermosetting composition containing an acrylic compound, which is obtained by adjusting the molecular weight of the epoxy compound of the present invention, has good heat resistance and improved scratch resistance (patent document 2).
With the recent demand for higher definition and thinner thickness in liquid crystal display devices, the protective film is required to have more excellent flatness than before. The flatness indicates a surface level difference when a protective film is applied to a color filter including pixels of red (R), green (G), blue (B), or the like used in a liquid crystal display element, and when the surface level difference is large, the display quality is degraded. Further improvement in flatness of the thermosetting material is a problem.
[ Prior art documents ]
[ patent document ]
[ patent document 1] Japanese patent laid-open No. 2005-
[ patent document 2] Japanese patent laid-open No. 2018-
Disclosure of Invention
[ problems to be solved by the invention ]
The present invention has been made in view of the above problems, and an object of the present invention is to provide a thermosetting composition which satisfies the above characteristics and gives a cured film having a more excellent flatness than before, a cured film formed from the thermosetting composition, and an electronic component having the cured film.
[ means for solving problems ]
The present inventors have made extensive studies to solve the above-mentioned problems, and as a result, they have found that the above-mentioned object can be achieved by a cured film obtained by curing a composition containing a polyesteramic acid which is a reaction product of a tetracarboxylic dianhydride, a diamine and a polyvalent hydroxyl compound, an epoxy compound, a compound having a polymerizable double bond, and a monofunctional acrylamide compound.
The present invention includes the following configurations.
[1] A thermosetting composition comprising a polyester amic acid (A), an epoxy compound (B), a compound (C) having a polymerizable double bond, and a monofunctional acrylamide compound (D), wherein the polyester amic acid (A) is a reaction product of raw materials comprising X moles of a tetracarboxylic dianhydride, Y moles of a diamine, and Z moles of a polyhydric hydroxyl compound at a ratio satisfying the relationship between the following formulae (1) and (2).
0.2≦Z/Y≦8.0·······(1)
0.2≦(Y+Z)/X≦5.0···(2)
[2] The thermosetting composition according to [1], wherein the polyesteramic acid (A) comprises a structural unit represented by the following formula (3) and a structural unit represented by the following formula (4).
In the formulae (3) and (4), R1Is a structure obtained by removing two groups-C (═ O) -O-C (═ O) -from a tetracarboxylic acid dianhydride, R is2For removing two-NH groups from diamines2To a structure of R3Is a structure obtained by removing two-OH groups from a polyvalent hydroxyl compound.
[3] The thermosetting composition according to [1] or [2], wherein the compound (C) having a polymerizable double bond is a compound having three or more (meth) acryloyl groups per molecule.
[4] The thermosetting composition according to any one of [1] to [3], wherein the content of the epoxy compound (B) is 20 to 400 parts by weight based on 100 parts by weight of the polyester amic acid (A), the content of the compound (C) having a polymerizable double bond is 1 to 200 parts by weight based on 100 parts by weight of the polyester amic acid (A), and the content of the monofunctional acrylamide compound (D) is 41 to 200 parts by weight based on 100 parts by weight of the polyester amic acid (A).
[5] The thermosetting composition according to any one of [1] to [3], wherein the content of the epoxy compound (B) is 20 to 400 parts by weight based on 100 parts by weight of the polyester amic acid (A), the content of the compound (C) having a polymerizable double bond is 1 to 200 parts by weight based on 100 parts by weight of the polyester amic acid (A), and the content of the monofunctional acrylamide compound (D) is 50 to 150 parts by weight based on 100 parts by weight of the polyester amic acid (A).
[6] A cured film obtained by curing the thermosetting composition according to any one of [1] to [5 ].
[7] A color filter having the cured film according to [6] as a transparent protective film.
[ Effect of the invention ]
The thermosetting composition according to a preferred embodiment of the present invention is particularly excellent in that a film having excellent flatness can be formed. For example, when the film is used as a protective film for a color filter of a color liquid crystal display element, the display quality can be improved. In particular, the composition is useful as a protective film for a color filter produced by a dyeing method, a pigment dispersion method, an electrodeposition method, and a printing method. In addition, the film can be used as an insulating film, a passivation film, a buffer coating film, or a planarization film of various electronic parts.
Detailed Description
In the present specification, the smaller the step of the cured film of the present invention is, the more excellent the cured film and the thermosetting composition for forming the cured film exhibit "flatness". The smaller the change in viscosity when the thermosetting material of the present invention is stored for a certain period of time, the more excellent the "storage stability".
In the present specification, the term "(meth) acrylate" may be used to indicate one or both of "acrylate" and "methacrylate". Similarly, to indicate one or both of "acryloyloxy" and "methacryloyloxy", the expression "(meth) acryloyloxy" is sometimes used.
1. The thermosetting composition of the present invention
The thermosetting composition of the present invention is a composition comprising a polyester amic acid which is a reaction product of raw materials comprising a tetracarboxylic dianhydride, a diamine and a polyhydroxyl compound, an epoxy compound, a compound having a polymerizable double bond, and a monofunctional acrylamide compound, and is characterized in that the epoxy compound is 20 to 400 parts by weight, the compound having a polymerizable double bond is 1 to 200 parts by weight, and the monofunctional acrylamide compound is 41 to 200 parts by weight, based on 100 parts by weight of the polyester amic acid.
1-1 polyester amic acid (A)
Polyesteramic acids are reaction products of starting materials comprising tetracarboxylic dianhydrides, diamines and polyhydroxyl compounds. More specifically, the polyesteramic acid is a reaction product of raw materials comprising X moles of a tetracarboxylic dianhydride, Y moles of a diamine, and Z moles of a polyhydric hydroxyl compound at a ratio satisfying the relationship of the following formulas (1) and (2).
0.2≦Z/Y≦8.0·······(1)
0.2≦(Y+Z)/X≦5.0···(2)
The polyesteramic acid (A) preferably has a constituent unit represented by the following formula (3) and a constituent unit represented by the following formula (4).
In the formulae (3) and (4), R1The tetracarboxylic dianhydride preferably has a structure in which two groups-C (═ O) -O-C (═ O) -are removed, and is preferably an organic group having 2 to 30 carbon atoms. R2For removing two-NH groups from diamines2The structure is preferably an organic group having 2 to 30 carbon atoms. R3The hydroxyl compound has a structure in which two-OH groups are removed from a polyvalent hydroxyl compound, and an organic group having 2 to 20 carbon atoms is preferable.
In the synthesis of the polyester amic acid (A), at least a solvent is required, and the solvent may be left as it is to prepare a liquid or gel-like thermosetting composition in consideration of handling properties and the like, or the solvent may be removed to prepare a solid composition in consideration of handling properties and the like. In the synthesis of the polyester amic acid (a), the raw material may optionally contain one or more compounds selected from the group consisting of monohydroxy compounds and styrene-maleic anhydride copolymers, and the monohydroxy compounds are particularly preferably contained. In the synthesis of the polyesteramic acid (A), other compounds than the above-mentioned ones may be optionally contained as starting materials within the range not prejudicial to the object of the present invention.
1-1-1 tetracarboxylic acid dianhydride
In the present invention, as a material for obtaining the polyesteramic acid (a), tetracarboxylic dianhydride is used. Specific examples of preferred tetracarboxylic dianhydrides are: 3,3',4,4' -benzophenonetetracarboxylic dianhydride, 2',3,3' -benzophenonetetracarboxylic dianhydride, 2,3,3',4' -benzophenonetetracarboxylic dianhydride, 3,3',4,4' -diphenylsulfonetetracarboxylic dianhydride, 2',3,3' -diphenylsulfonetetracarboxylic dianhydride, 2,3,3',4' -diphenylsulfonetetracarboxylic dianhydride, 3,3',4,4' -diphenylethertetracarboxylic dianhydride, 2',3,3' -diphenylethertetracarboxylic dianhydride, 2,3,3',4' -diphenylethertetracarboxylic dianhydride, 2- [ bis (3, 4-dicarboxyphenyl) ] hexafluoropropane dianhydride, 1,2,3, 4-butanetetracarboxylic dianhydride, ethylene glycol bis (anhydrotrimellitate) (trade name; TMEG-100, new york physics and chemistry limited), 1,2,3, 4-cyclobutanetetracarboxylic dianhydride, 1,2,3, 4-cyclopentanetetracarboxylic dianhydride, 1,2,4, 5-cyclohexanetetracarboxylic dianhydride, and ethane-1, 1,2, 2-tetracarboxylic dianhydride. One or more of these tetracarboxylic dianhydrides can be used.
Among these tetracarboxylic acid dianhydrides, 3',4,4' -diphenylsulfone tetracarboxylic acid dianhydride, 3',4,4' -diphenylether tetracarboxylic acid dianhydride, 2- [ bis (3, 4-dicarboxyphenyl) ] hexafluoropropane dianhydride, 1,2,3, 4-butanetetracarboxylic acid dianhydride and ethylene glycol bis (anhydrotrimellitate) which impart good transparency are more preferable, and 3,3',4,4' -diphenylsulfone tetracarboxylic acid dianhydride, 3',4,4' -diphenylether tetracarboxylic acid dianhydride and 1,2,3, 4-butanetetracarboxylic acid dianhydride are still more preferable.
1-1-2-diamines
In the present invention, as a material for obtaining the polyesteramic acid (A), a diamine is used. Specific examples of preferred diamines are: 4,4' -diaminodiphenyl sulfone, 3' -diaminodiphenyl sulfone, 3,4' -diaminodiphenyl sulfone, bis [4- (4-aminophenoxy) phenyl ] sulfone, bis [4- (3-aminophenoxy) phenyl ] sulfone, bis [3- (4-aminophenoxy) phenyl ] sulfone, [4- (4-aminophenoxy) phenyl ] [3- (4-aminophenoxy) phenyl ] sulfone, [4- (3-aminophenoxy) phenyl ] [3- (4-aminophenoxy) phenyl ] sulfone, and 2, 2-bis [4- (4-aminophenoxy) phenyl ] hexafluoropropane. One or more of these diamines may be used.
Among these diamines, 3 '-diaminodiphenyl sulfone or bis [4- (3-aminophenoxy) phenyl ] sulfone which imparts good transparency is more preferable, and 3,3' -diaminodiphenyl sulfone is still more preferable.
1-1-3. polybasic hydroxy compound
In the present invention, as a material for obtaining the polyesteramic acid (A), a polyhydric hydroxyl compound is used.
Specific examples of the polyhydric hydroxyl compound include: ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol having a weight average molecular weight of 1,000 or less, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, polypropylene glycol having a weight average molecular weight of 1,000 or less, 1, 2-butanediol, 1, 3-butanediol, 1, 4-butanediol, 1, 2-pentanediol, 1, 5-pentanediol, 2, 4-pentanediol, 1,2, 5-pentanetriol, 1, 2-hexanediol, 1, 6-hexanediol, 2, 5-hexanediol, 1,2, 6-hexanetriol, 1, 2-heptanediol, 1, 7-heptanediol, 1,2, 7-heptanetriol, 1, 2-octanediol, 1, 8-octanediol, 3, 6-octanediol, 1,2, 8-octanetriol, 1, 2-nonanediol, 1, 9-nonanediol, 1,2, 9-nonanetriol, 1, 2-decanediol, 1, 10-decanediol, 1,2, 10-decanetriol, 1, 2-dodecanediol, 1, 12-dodecanediol, glycerol, trimethylolpropane, pentaerythritol, dipentaerythritol, tris (2-hydroxyethyl) isocyanurate, bisphenol A (2, 2-bis (4-hydroxyphenyl) propane), bisphenol S (bis (4-hydroxyphenyl) sulfone), bisphenol F (bis (4-hydroxyphenyl) methane), 4 '-isopropylidenebis (2-phenoxyethanol), 2-bis (4-hydroxycyclohexyl) propane, 4' -dihydroxydicyclohexyl, 2-hydroxybenzyl alcohol, 4-hydroxybenzyl alcohol, 2- (4-hydroxyphenyl) ethanol, diethanolamine, triethanolamine, glycerol monoallyl ether, trimethylolpropane monoallyl ether, pentaerythritol diallyl ether, dipentaerythritol monoallyl ether, dipentaerythritol diallyl ether, dipentaerythritol triallyl ether, dipentaerythritol tetraallyl ether, sorbitol monoallyl ether, sorbitol diallyl ether, sorbitol triallyl ether, sorbitol tetraallyl ether, glycerol mono (meth) acrylate, trimethylolpropane mono (meth) acrylate, pentaerythritol di (meth) acrylate, dipentaerythritol mono (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate, di (, Dipentaerythritol tetra (meth) acrylate, sorbitol mono (meth) acrylate, sorbitol di (meth) acrylate, sorbitol tri (meth) acrylate, sorbitol tetra (meth) acrylate, a (meth) acrylic acid modified product of ethylene glycol diglycidyl ether, a (meth) acrylic acid modified product of propylene glycol diglycidyl ether, a (meth) acrylic acid modified product of tripropylene glycol diglycidyl ether, a (meth) acrylic acid modified product of glycerol diglycidyl ether, a (meth) acrylic acid modified product of bisphenol a diglycidyl ether, a (meth) acrylic acid modified product of propylene oxide-modified bisphenol a diglycidyl ether, a (meth) acrylic acid modified product of bisphenol S diglycidyl ether, a (meth) acrylic acid modified product of propylene oxide-modified bisphenol S diglycidyl ether, a (meth) acrylic acid modified product of bisphenol F diglycidyl ether, a mixture of these two components, A (meth) acrylic acid-modified product of propylene oxide-modified bisphenol F diglycidyl ether, a (meth) acrylic acid-modified product of bithiophenol diglycidyl ether, a (meth) acrylic acid-modified product of biphenol diglycidyl ether, a (meth) acrylic acid-modified product of fluorene bisphenol diglycidyl ether, a (meth) acrylic acid-modified product of cyclohexane-1, 4-dimethanol diglycidyl ether, a (meth) acrylic acid-modified product of hydrogenated bisphenol a diglycidyl ether, a (meth) acrylic acid-modified product of tricyclodecane dimethanol diglycidyl ether, and a (meth) acrylic acid-modified product of another compound having two or more epoxy groups per molecule.
Of these polyhydric hydroxyl compounds, preferred are ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 7-heptanediol, 1, 8-octanediol, tris (2-hydroxyethyl) isocyanurate, 2-bis (4-hydroxycyclohexyl) propane, 4 '-dihydroxydicyclohexyl, 2-hydroxybenzyl alcohol, 4-hydroxybenzyl alcohol, 2- (4-hydroxyphenyl) ethanol, 4' -isopropylidenebis (2-phenoxyethanol), a (meth) acrylic acid-modified product of ethylene glycol diglycidyl ether, a (meth) acrylic acid-modified product of propylene glycol diglycidyl ether, a (meth) acrylic acid-modified product of glycerol diglycidyl ether, A (meth) acrylic acid-modified product of bisphenol a diglycidyl ether, a (meth) acrylic acid-modified product of propylene oxide-modified bisphenol a diglycidyl ether, a (meth) acrylic acid-modified product of bisphenol S diglycidyl ether, a (meth) acrylic acid-modified product of propylene oxide-modified bisphenol S diglycidyl ether, a (meth) acrylic acid-modified product of bisphenol F diglycidyl ether, or a (meth) acrylic acid-modified product of propylene oxide-modified bisphenol F diglycidyl ether. Still more particularly, diethylene glycol, triethylene glycol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 2-hydroxybenzyl alcohol, 4' -isopropylidene bis (2-phenoxyethanol), 2- (4-hydroxyphenyl) ethanol, a (meth) acrylic acid modified product of ethylene glycol diglycidyl ether, a (meth) acrylic acid modified product of propylene glycol diglycidyl ether, a (meth) acrylic acid modified product of tripropylene glycol diglycidyl ether, a (meth) acrylic acid modified product of glycerol diglycidyl ether, a (meth) acrylic acid modified product of bisphenol a diglycidyl ether, or a (meth) acrylic acid modified product of propylene oxide-modified bisphenol a diglycidyl ether are more preferable.
As the methacrylic acid-modified product of ethylene glycol diglycidyl ether, the acrylic acid-modified product of propylene glycol diglycidyl ether, the acrylic acid-modified product of tripropylene glycol diglycidyl ether, the acrylic acid-modified product of glycerol diglycidyl ether, the methacrylic acid-modified product of bisphenol a diglycidyl ether, the acrylic acid-modified product of bisphenol a diglycidyl ether, the methacrylic acid-modified product of propylene oxide-modified bisphenol a diglycidyl ether, and the acrylic acid-modified product of propylene oxide-modified bisphenol a diglycidyl ether, the following commercially available products can be used.
A specific example of the methacrylic acid-modified product of ethylene glycol diglycidyl ether is epoxy ester 40EM (trade name; Kyoeisha chemical Co., Ltd.). A specific example of the acrylic modified product of propylene glycol diglycidyl ether is epoxy ester 70PA (trade name; Kyoeisha chemical Co., Ltd.). A specific example of the acrylic modified product of tripropylene glycol diglycidyl ether is epoxy ester 200PA (trade name; Kyoeisha chemical Co., Ltd.). A specific example of the acrylic modified product of glycerol diglycidyl ether is epoxy ester 80MFA (trade name; Kyoeisha chemical Co., Ltd.). A specific example of the methacrylic acid-modified product of bisphenol A diglycidyl ether is epoxy ester 3000MK (trade name; Kyoeisha chemical Co., Ltd.). A specific example of the acrylic modified product of bisphenol A diglycidyl ether is epoxy ester 3000A (trade name; Kyoeisha chemical Co., Ltd.). A specific example of the methacrylic acid-modified product of propylene oxide-modified bisphenol A diglycidyl ether is epoxy ester 3002M (N) (trade name; Kyoeisha chemical Co., Ltd.). A specific example of the acrylic modified product of propylene oxide-modified bisphenol A diglycidyl ether is epoxy ester 3002A (N) (trade name; Kyoeisha chemical Co., Ltd.).
1-1-4 monohydroxy compound
In the present invention, as a material to obtain the polyester amic acid (a), a monohydroxy compound can be used. By using the monohydroxy compound, the storage stability of the thermosetting composition is improved. Specific examples of preferred monohydroxy compounds are: methanol, ethanol, 1-propanol, isopropanol, allyl alcohol, benzyl alcohol, propylene glycol monoethyl ether, propylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, phenol, borneol (borneel), maltitol (maltol), linalool (linalool), terpineol (terpineol), dimethylbenzyl methanol (dimethyl benzyl carbinol) and 3-ethyl-3-hydroxymethyl oxetane. One or more of these monohydroxy compounds may be used.
Of these monohydroxy compounds, isopropyl alcohol, allyl alcohol, benzyl alcohol, propylene glycol monoethyl ether, or 3-ethyl-3-hydroxymethyloxetane is more preferable. In view of compatibility when the polyester amic acid (a), the epoxy compound (B), the compound having a polymerizable double bond (C), and the monofunctional acrylamide compound (D) formed using these monohydroxy compounds are mixed, or coatability of the thermosetting composition on a color filter, it is more preferable to use benzyl alcohol as the monohydroxy compound.
The reaction is preferably carried out by including 0 to 300 parts by weight of the monohydroxy compound per 100 parts by weight of the total amount of the tetracarboxylic dianhydride, the diamine, and the polyhydroxy compound. More preferably 5 to 200 parts by weight.
1-1-5 styrene-maleic anhydride copolymer
The polyesteramic acid (A) used in the present invention may be synthesized by adding a compound having three or more acid anhydride groups to the above-mentioned raw materials. The polyester amic acid (A) synthesized by adding a compound having three or more acid anhydride groups is preferable because improvement in transparency is expected. Examples of the compound having three or more acid anhydride groups are styrene-maleic anhydride copolymers. The ratio of each component constituting the styrene-maleic anhydride copolymer is 0.5 to 4, preferably 1 to 3, in terms of the molar ratio of styrene/maleic anhydride. The styrene/maleic anhydride molar ratio is more preferably 1 or 2, and still more preferably 1.
Specific examples of the styrene-maleic anhydride copolymer are SMA3000P, SMA2000P and SMA1000P (all trade names; Sichuan crude oil Co., Ltd.). Among these styrene-maleic anhydride copolymers, SMA1000P excellent in heat resistance and alkali resistance is particularly preferable.
The styrene-maleic anhydride copolymer is preferably contained in an amount of 0 to 500 parts by weight based on 100 parts by weight of the total amount of the tetracarboxylic dianhydride, the diamine and the polyhydroxyl compound. More preferably 10 to 300 parts by weight.
1-1-6 aminosilane compound having one amino group
In the synthesis of the polyester amic acid (a), other raw materials than those described above may be included as necessary as raw materials within the scope not detracting from the object of the present invention, and an aminosilane compound having one amino group is an example of such other raw materials. The aminosilane compound having one amino group is used to react with the acid anhydride group at the terminal of the polyester amic acid (A) to introduce a silane group at the terminal. The acid resistance of the cured film obtained can be improved by using the thermosetting composition of the present invention containing a polyesteramic acid (A) obtained by adding an aminosilane compound having one amino group for reaction. Further, in the case of carrying out the reaction in the above-mentioned monomer composition, both a monohydroxy compound and an aminosilane compound having one amino group may be added to carry out the reaction.
Specific examples of the aminosilane compound having one amino group used in the present invention are: 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, 4-aminobutyltrimethoxysilane, 4-aminobutyltriethoxysilane, 4-aminobutylmethyldiethoxysilane, p-aminophenyltrimethoxysilane, p-aminophenyltriethoxysilane, p-aminophenylmethyldimethoxysilane, p-aminophenylmethyldiethoxysilane, m-aminophenyltrimethoxysilane and m-aminophenylmethyldiethoxysilane. More than one of these compounds may be used.
Among these compounds, 3-aminopropyltriethoxysilane and p-aminophenyltrimethoxysilane which are excellent in acid resistance of the cured film are more preferable, and 3-aminopropyltriethoxysilane is still more preferable from the viewpoint of acid resistance and compatibility.
The aminosilane compound having one amino group is preferably contained in an amount of 0 to 300 parts by weight based on 100 parts by weight of the total amount of the tetracarboxylic dianhydride, the diamine and the polyhydric hydroxyl compound. More preferably 5 to 200 parts by weight.
1-1-7 solvent used in the Synthesis reaction of polyesteramic acid (A)
Specific examples of the solvent used in the synthesis reaction for obtaining the polyester amic acid (a) (hereinafter sometimes referred to as "reaction solvent") are: diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, diethylene glycol monoethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, ethyl lactate, cyclohexanone, N-methyl-2-pyrrolidone, and N, N-dimethylacetamide. Of these solvents, propylene glycol monomethyl ether acetate, methyl 3-methoxypropionate, or diethylene glycol methyl ethyl ether is preferable.
1-1-8. method for synthesizing polyesteramic acid (A)
The polyesteramic acid (a) used in the present invention is preferably synthesized by reacting X moles of tetracarboxylic dianhydride, Y moles of diamine, and Z moles of a polyvalent hydroxyl compound in the solvent, wherein X, Y and Z are defined as the proportions in which the following formulas (1) and (2) hold between them. When the content is in the above range, the solubility of the polyesteramic acid (A) in the solvent is high, and therefore the coating property of the composition is improved, and as a result, a cured film having excellent flatness can be obtained.
0.2≦Z/Y≦8.0·······(1)
0.2≦(Y+Z)/X≦5.0···(2)
In the formula (1), it is preferably 0.7. ltoreq. Z/Y. ltoreq.7.0, more preferably 1.0. ltoreq. Z/Y. ltoreq.5.0. In formula (2), it is preferably 0.5 ≦ (Y + Z)/X ≦ 4.0, and more preferably 0.6 ≦ (Y + Z)/X ≦ 2.0.
It is considered that the polyesteramic acid (a) used in the present invention is a molecule having an acid anhydride group (-C (═ O) -O-C (═ O) -) at the terminal, in excess of the molecule having an amino group or a hydroxyl group at the terminal, under the condition that X is used in excess relative to (Y + Z) in the above reaction conditions. In the case of carrying out the reaction in such a monomer configuration, the monohydroxy compound may be added as necessary in order to esterify the terminal in order to react with an acid anhydride group at the molecular terminal. The polyester amic acid (A) obtained by the reaction with the addition of the monohydroxy compound improves the compatibility with the epoxy compound and the epoxy curing agent, and improves the coatability of the thermosetting composition of the present invention containing these compounds.
It is preferable to use 100 to 1000 parts by weight of the reaction solvent based on 100 parts by weight of the total of the tetracarboxylic dianhydride, the diamine and the polyhydroxyl compound, because the reaction proceeds smoothly. The reaction is preferably carried out at 40 ℃ to 200 ℃ for 0.2 hour to 20 hours.
The order of addition of the reaction raw materials to the reaction system is not particularly limited. That is, any of the following methods may be used: a method of simultaneously adding tetracarboxylic dianhydride, diamine and a polyvalent hydroxyl compound to a reaction solvent; a method in which a diamine and a polyvalent hydroxyl compound are dissolved in a reaction solvent, and then a tetracarboxylic dianhydride is added; a method in which a tetracarboxylic dianhydride and a polyhydric hydroxyl compound are reacted in advance, and then a diamine is added to the product; or a method in which a tetracarboxylic dianhydride and a diamine are reacted in advance, and then a polyvalent hydroxy compound is added to the resultant.
When the aminosilane compound having one amino group is reacted, after the reaction of the mixture of the tetracarboxylic dianhydride, the diamine and the polyhydroxyl compound is completed, the solution after the reaction is cooled to 40 ℃ or less, and then the aminosilane compound having one amino group is added and the reaction is carried out at 10 to 40 ℃ for 0.1 to 6 hours. Further, the monohydroxy compound may be added at an arbitrary point of time during the reaction.
The polyesteramic acid (A) synthesized in the above-described manner comprises a constituent unit represented by the formula (3) and a constituent unit represented by the formula (4), and the terminal thereof is an acid anhydride group, an amino group or a hydroxyl group derived from a tetracarboxylic dianhydride, a diamine or a polyvalent hydroxyl compound as a raw material, or an additive other than these compounds constitutes the terminal thereof. By including such a constitution, the hardenability becomes excellent.
The polyester amic acid (A) obtained preferably has a weight average molecular weight of 1,000 to 200,000, more preferably 2,000 to 50,000. When the amount is in these ranges, the flatness and heat resistance are improved.
The weight average molecular weight of the polyesteramic acid (A) is a value in terms of polystyrene determined by the Gel Permeation Chromatography (GPC) method (column temperature: 35 ℃ C., flow rate: 1 ml/min). Standard polystyrene was used with weight average molecular weights of 645, 2590, 10290, 37600, and 124500 using the polystyrene calibration kit (calibration kit) PL2010-0102 from Agilent Technologies, Inc. The column used PL gel mixing (PLGel MIXED) -D (Agilent Technologies, Inc.) using Tetrahydrofuran (THF) as the mobile phase. The weight average molecular weight of the commercially available polymer described in the present specification is a value described in a catalog (catalog).
1-2 epoxy compound (B)
The epoxy compound (B) used in the present invention is a compound having two or more epoxy groups per molecule.
Examples of epoxy compounds (B) are: bisphenol a-type epoxy compounds, bisphenol F-type epoxy compounds, glycidyl ether-type epoxy compounds, glycidyl ester-type epoxy compounds, biphenyl-type epoxy compounds, phenol novolac-type epoxy compounds, cresol novolac-type epoxy compounds, bisphenol a novolac-type epoxy compounds, aliphatic polyglycidyl ether compounds, cyclic aliphatic epoxy compounds, copolymers of monomers having an epoxy group and other monomers, and epoxy compounds having a siloxane bonding site.
Specific examples of commercially available products of bisphenol A type epoxy compounds are jER 828, jER 1004, jER 1009 (both trade names; Mitsubishi chemical Co., Ltd.); specific examples of commercially available products of bisphenol F type epoxy compounds are jER 806, jER 4005P (both trade names; Mitsubishi chemical Co., Ltd.); specific examples of commercially available products of glycidyl ether type epoxy compounds are TechMORE (TECHMEE) VG3101L (trade name; Printec (Printec) Co., Ltd.), EHPE3150 (trade name; Daicel (Daicel) Co., Ltd.), EPPN-501H, EPPN-502H (both trade names; Nippon chemical Co., Ltd.) and jER 1032H60 (trade name; Mitsubishi chemical Co., Ltd.); specific examples of commercially available products of glycidyl ester type epoxy compounds are danacol (Denacol) EX-721 (trade name; tradename: stamen chemie x) and 1, 2-cyclohexanedicarboxylic acid diglycidyl ester (trade name; manufactured by tokyo chemical industries, ltd.); specific examples of the biphenyl type epoxy compounds which are commercially available are jER YX4000, jER YX4000H, jER YL6121H (both trade names; Mitsubishi chemical Co., Ltd.), NC-3000-L, NC-3000-H, NC-3100 (both trade names; Nippon chemical Co., Ltd.); specific examples of commercially available products of phenol novolak type epoxy compounds include EPPN-201 (trade name; Nippon chemical Co., Ltd.), JeR 152 and JeR 154 (trade name; Mitsubishi chemical Co., Ltd.), and the like; specific examples of commercially available products of cresol novolak type epoxy compounds are EOCN-102S, EOCN-103S, EOCN-104S, EOCN-1020 (all trade names; Nippon chemical Co., Ltd.) and the like; specific examples of commercially available products of bisphenol A novolak-type epoxy compounds are jER 157S65, jER 157S70 (both trade names; Mitsubishi chemical Co., Ltd.); specific examples of commercially available products of cyclic aliphatic epoxy compounds are sirolimus (Celloxide)2021P and sirolimus (Celloxide)3000 (trade names; Daicel, Co., Ltd.); specific examples of commercially available epoxy compounds having a siloxane bonding site are 1, 3-bis [2- (3, 4-epoxycyclohexyl) ethyl ] tetramethyldisiloxane (trade name; Gelest Incorporated), TSL9906 (trade name; Japanese Mammy advanced Materials Japan, Ltd.), Cooteosil (COATASIL) MP200 (trade name; Japanese Mammy advanced Materials Japan, Ltd.), Marron SQ506 (trade name; Arakawa chemical Co., Ltd.), ES-1023 (trade name; Trans chemical industry Co., Ltd.).
Further, TechMORE (TECHMORE) VG3101L (trade name; Printtaceae (Printec) Co., Ltd.) was a mixture of 2- [4- (2, 3-epoxypropoxy) phenyl ] -2- [4- [1, 1-bis [4- (2, 3-epoxypropoxy) phenyl ] ethyl ] phenyl ] propane and 1, 3-bis [4- [1- [4- (2, 3-epoxypropoxy) phenyl ] -1-methylethyl ] phenyl ] ethyl ] phenoxy ] -2-propanol; EHPE3150 (trade name; Daicel, Inc.) is a1, 2-epoxy-4- (2-oxetanyl) cyclohexane adduct of 2, 2-bis (hydroxymethyl) -1-butanol; cyrocide (Celloxide)2021P (trade name; Daiil (Daicel) Co., Ltd.) is 3',4' -epoxycyclohexylmethyl-3, 4-epoxycyclohexanecarboxylate; cyrocide (Celloxide)3000 (trade name; Daicel, Inc.) is 1-methyl-4- (2-methyl-oxacyclopropyl) -7-oxabicyclo [4.1.0] heptane; CooteOslo (COATOSIL) MP200 (trade name; Japanese Mayer Material Ltd.) is a polymer of 3-glycidoxypropyltrimethoxysilane.
Among these epoxy compounds, the epoxy compound (B) is preferably a bisphenol a type epoxy compound, a bisphenol F type epoxy compound, a glycidyl ether type epoxy compound, a glycidyl ester type epoxy compound, a biphenyl type epoxy compound, an aliphatic polyglycidyl ether compound, a cyclic aliphatic epoxy compound, a copolymer of a monomer having an epoxy group and another monomer, or an epoxy compound having a siloxane bond site. The epoxy compound (B) is more preferably a bisphenol a type epoxy compound, a glycidyl ether type epoxy compound, a copolymer of a monomer having an epoxy group and another monomer, or an epoxy compound having a siloxane bond site.
The epoxy compound (B) may be used alone or in combination of two or more.
The total amount of the epoxy compound (B) is 20 to 400 parts by weight based on 100 parts by weight of the polyesteramic acid (A) in the thermosetting composition of the present invention. When the ratio of the total amount of the epoxy compound (B) is in the above range, the balance among flatness, heat resistance, chemical resistance and adhesion is good. The total amount of the epoxy compound (B) is more preferably in the range of 50 to 300 parts by weight.
1-3 Compound (C) having polymerizable double bond
The compound (C) having a polymerizable double bond used in the present invention is not particularly limited as long as it has three or more (meth) acryloyl groups per molecule.
Specific examples of the compound having three or more (meth) acryloyl groups per molecule in the compound (C) having a polymerizable double bond are: trimethylolpropane tri (meth) acrylate, ethylene oxide-modified trimethylolpropane tri (meth) acrylate, propylene oxide-modified trimethylolpropane tri (meth) acrylate, epichlorohydrin-modified trimethylolpropane tri (meth) acrylate, glycerol tri (meth) acrylate, epichlorohydrin-modified glycerol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, alkyl-modified dipentaerythritol tri (meth) acrylate, ethylene oxide-modified phosphoric acid tri (meth) acrylate, caprolactone/ethylene oxide-modified phosphoric acid tri (meth) acrylate, caprolactone-modified tris [ (meth) acryloyloxyethyl ] isocyanurate, di-trimethylolpropane tetra (meth) acrylate, diglycerol tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, propylene oxide tri (meth) acrylate, propylene oxide, Alkyl-modified dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, alkyl-modified dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, caprolactone-modified dipentaerythritol hexa (meth) acrylate, and carboxyl-containing polyfunctional (meth) acrylate.
The compounds having a polymerizable double bond may be used alone or in combination of two or more.
Among the compounds having a polymerizable double bond, at least one selected from the group consisting of ethylene oxide isocyanurate-modified triacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, and carboxyl group-containing polyfunctional (meth) acrylate is preferably used from the viewpoint of flatness and scratch resistance.
As the compound having a polymerizable double bond, commercially available compounds such as those described below can be used. A specific example of the mixture of the isocyanurate ethylene oxide-modified triacrylates is M-315(3 to 13% by weight, hereinafter abbreviated as "M-315") (trade name; Toyo Synthesis Co., Ltd., the content in parentheses is a value described in the table of the content of the isocyanurate ethylene oxide-modified triacrylate in the mixture); specific examples of trimethylolpropane triacrylate are Aronix M-309 (trade name; Toyo Synthesis Co., Ltd.); specific examples of the mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate include Aronix M-306(65 to 70 wt%), Aronix M-305(55 to 63 wt%), Aronix M-303(30 to 60 wt%), Aronix M-452(25 to 40 wt%) and Aronix M-450 (less than 10 wt%) (trade names; Toya Synthesis Co., Ltd., the content in parentheses is a value listed as the content of pentaerythritol triacrylate in the mixture); specific examples of the mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate include Aronix M-403(50 to 60 wt%), Aronix M-400(40 to 50 wt%), Aronix M-402(30 to 40 wt%, hereinafter abbreviated as "M-402"), Aronix M-404(30 to 40 wt%), Aronix M-406(25 to 35 wt%) and Aronix M-405(10 to 20 wt%) (both trade names; Toyo synthetic Co., Ltd., the content in parentheses is a value described in the table of the content of dipentaerythritol pentaacrylate in the mixture); specific examples of the carboxyl group-containing polyfunctional (meth) acrylate are Aronix M-510 and Aronix M-520 (hereinafter, abbreviated as "M-520") (both trade names; Toyo Synthesis Co., Ltd.).
The proportion of the total amount of the compound (C) having a polymerizable double bond is 1 to 200 parts by weight based on 100 parts by weight of the polyesteramic acid (A) in the thermosetting composition of the present invention. When the proportion of the total amount of the compound (C) having a polymerizable double bond is in the above range, the balance between the flatness and the scratch resistance is good. The total amount of the compound (C) having a polymerizable double bond is more preferably in the range of 50 to 150 parts by weight.
1-4. monofunctional acrylamide Compound (D)
The monofunctional acrylamide compound (D) used in the present invention is not particularly limited as long as it has one acrylamide group per molecule.
Specific examples of the monofunctional acrylamide compound (D) are: acrylamide, N-N-butoxymethylacrylamide, N-isobutoxymethylacrylamide, N-dimethylacrylamide, N-diethylacrylamide, N- (hydroxymethyl) acrylamide, N- (2-hydroxyethyl) acrylamide, 6-acrylamidohexanoic acid, 2-acrylamido-2-methylpropanesulfonic acid, N-tert-butylacrylamide, diacetoneacrylamide, N- [3- (dimethylamino) propyl ] acrylamide, N-dodecylacrylamide, N-isopropylacrylamide, N-phenylacrylamide, N- (1,1,3, 3-tetramethylbutyl) acrylamide, 3-acrylamidophenylboronic acid.
As the monofunctional acrylamide compound (D), commercially available products such as those described below can be used. N-N-butoxymethylacrylamide (trade name; MCC Unitec, Inc.), N-isobutoxymethylacrylamide (trade name; MCC Unitec, Inc.), Diethylacrylamide (DEAA) (trade name; Xingan, Inc.), hydroxyethylacrylamide (Hydroxy Ethyl Acrylamide, HEAA) (trade name; KJ chemistry (CHEMICALS), N-dimethylacrylamide (trade name; KJ chemistry (CHEMICALS), Inc.).
Among these acrylamide compounds, the monofunctional acrylamide compound (D) is preferably at least one compound selected from the group consisting of acrylamide, N-N-butoxymethylacrylamide, N-isobutoxymethylacrylamide, N-dimethylacrylamide, N-diethylacrylamide, N- (hydroxymethyl) acrylamide, N- (2-hydroxyethyl) acrylamide, and 6-acrylamidocaproic acid. Further, the monofunctional acrylamide compound (D) is more preferably at least one compound selected from the group consisting of N-N-butoxymethylacrylamide, N-isobutoxymethylacrylamide, N-dimethylacrylamide, N-diethylacrylamide, N- (hydroxymethyl) acrylamide and N- (2-hydroxyethyl) acrylamide.
The monofunctional acrylamide compound (D) may be used alone or in combination of two or more.
The proportion of the total amount of the monofunctional acrylamide compound (D) is preferably in the range of 41 to 200 parts by weight based on 100 parts by weight of the polyester amic acid (a) in the thermosetting composition of the present invention. When the proportion of the total amount of the monofunctional acrylamide compound (D) is in the above range, the balance among flatness, scratch resistance and storage stability is good. The proportion of the total amount of the monofunctional acrylamide compound (D) is more preferably in the range of 50 to 150 parts by weight.
1-5. other ingredients
Various additives may be added to the thermosetting composition of the present invention to improve coating uniformity and adhesion. The additives can be mainly listed as follows: a hardening agent; a solvent; an anionic, cationic, nonionic, fluorine-based or silicon-based surfactant/leveling agent; adhesion improving agents such as silane coupling agents; antioxidants such as hindered phenol compounds, hindered amine compounds, phosphorus compounds and sulfur compounds; a molecular weight regulator; an ultraviolet absorber; an anti-agglomerating agent; a thermal cross-linking agent; styrene-maleic anhydride copolymers and other additives.
1-5-1 hardening agent
In the thermosetting composition of the present invention, a curing agent may be used to further improve heat resistance and chemical resistance. As the curing agent, there are an acid anhydride curing agent, an amine curing agent, a phenol curing agent, a carboxylic acid-containing polymer, an imidazole curing agent, a pyrazole curing agent, a triazole curing agent, a catalyst type curing agent, and a heat-sensitive acid generator such as a sulfonium salt, a benzothiazolium salt, an ammonium salt, and a phosphonium salt, and from the viewpoint of preventing coloration of the cured film and heat resistance of the cured film, an acid anhydride curing agent, an imidazole curing agent, or a pyrazole curing agent is preferable.
Specific examples of the acid anhydride-based curing agent are: aliphatic dicarboxylic acid anhydrides such as maleic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, and hexahydrotrimellitic anhydride; aromatic polycarboxylic acid anhydrides such as phthalic anhydride and trimellitic anhydride; and styrene-maleic anhydride copolymers. Among these acid anhydride-based curing agents, trimellitic anhydride and hexahydrotrimellitic anhydride, which have a good balance between heat resistance and solubility in solvents, can be cited.
Specific examples of the carboxylic acid-containing polymer include: ARUFON UC-3000, ARUFON UC-3090, ARUFON UC-3900 (trade name; tokyo synthetic corporation), marpoof (Marproof) MA-0215Z, marpoof (Marproof) MA-0217Z, and marpoof (marpoof) MA-0221Z (trade name; japan oil limited). Among these carboxylic acid-containing polymers, preferred is alufon UC-3900 which is excellent in heat resistance, solubility in solvents, and flatness.
Specific examples of the imidazole-based curing agent are: 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2, 3-dihydro-1H-pyrrolo [1,2-a ] benzimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-benzyl-2-methylimidazole and 1-benzyl-2-phenylimidazole. Among these imidazole-based curing agents, there are 2-undecylimidazole, 2-phenyl-4-methylimidazole and 1-benzyl-2-phenylimidazole, which have a good balance between curing properties and solubility in solvents.
Specific examples of the pyrazole-based curing agent are: pyrazole, 3-methylpyrazole, 3, 5-dimethylpyrazole, 3-methyl-5-pyrazolone. 3, 5-dimethylpyrazole having a good balance between curability and solubility in a solvent is preferable.
Specific examples of the triazole-based curing agent are: 4-amino-1, 2, 4-triazole, 1,2, 3-triazole, 1-hydroxybenzotriazole, 3-mercapto-1, 2, 4-triazole. 1-hydroxybenzotriazole is preferable, which has a good balance between curability and solubility in a solvent.
Specific examples of the phenolic curing agent include: α, α, α '-tris (4-hydroxyphenyl) -1-ethyl-4-isopropylbenzene, 1,1, 1-tris (4-hydroxyphenyl) ethane, 9-bis (4-hydroxy-3-methylphenyl) fluorene, 1, 3-bis [2- (4-hydroxyphenyl) -2-propyl ] benzene, 4' - (3,3, 5-trimethyl-1, 1-cyclohexanediyl) bis (phenol), and 1,1,2, 2-tetrakis (4-hydroxyphenyl) ethane. Among these phenolic hardeners, α, α, α' -tris (4-hydroxyphenyl) -1-ethyl-4-isopropylbenzene, 1,1, 1-tris (4-hydroxyphenyl) ethane, and 9, 9-bis (4-hydroxy-3-methylphenyl) fluorene, which are excellent in balance between heat resistance and compatibility, are listed.
When the curing agent is used, the amount is preferably in the range of 0.1 to 60 parts by weight per 100 parts by weight of the epoxy compound (B).
1-5-2. solvent
In the thermosetting composition of the present invention, a solvent may be used. The solvent optionally added to the thermosetting composition of the present invention is preferably a solvent in which the polyesteramic acid (A), the epoxy compound (B), the compound (C) having a polymerizable double bond, and the monofunctional acrylamide compound (D) are soluble. Specific examples of the solvent are: methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutanol, tert-butanol, acetone, 2-butanone, ethyl acetate, butyl acetate, propyl acetate, butyl propionate, ethyl lactate, methyl glycolate, ethyl glycolate, butyl glycolate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-oxopropionate, ethyl 3-hydroxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-hydroxypropionate, propyl 2-hydroxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, isopropyl 2-ethoxypropionate, isopropyl 2-methyl, Methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutyrate, ethyl 2-oxobutyrate, 4-hydroxy-4-methyl-2-pentanone, 1, 4-butanediol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether, propylene glycol, methyl propionate, Ethylene glycol monobutyl ether acetate, cyclopentanone, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, tetrahydrofuran, acetonitrile, dioxane, toluene, xylene, gamma-butyrolactone, N-dimethylacetamide, cyclohexanone, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycols having a weight average molecular weight of 1,000 or less, propylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, and polypropylene glycols having a weight average molecular weight of 1,000 or less. The solvent may be one of these solvents, or may be a mixture of two or more of these solvents.
The content of the solvent is preferably 65 to 95 parts by weight based on the total amount of the thermosetting composition. More preferably 70 to 90 parts by weight.
1-5-3. surfactant
In the thermosetting composition of the present invention, a surfactant may be added to improve coating uniformity. Specific examples of the surfactant are: polyflow No.75, Polyflow No.90, Polyflow No.95, DISPERBYK 161, DISPERBYK 162, DISPERBYK 163, DISPERBYK 164, DISPERBYK 166, DISPERBYK 170, DISPERBYK 180, DISPERBYK 181, DISPERBYK 182, BYK-300, BYK-306, BYK-310, BYK-320, BYK-330, BYK-361N, BYK, UV-N, BYK, and PenerbyK-3500, KP-368, KF-96-50CS, KF-50-100CS (trade names; shin-Etsu Chemical industries, Ltd.), Sanflon (Surflon) S611 (trade names; AGC Seimi Chemical industries, Ltd.), Forget (Ftergent)222F, Forget (Ftergent)208G, Forget (Ftergent)251, Forget (Ftergent)710FL, Forget (Ftergent)710FM, Forget (Ftergent)710FS, Forget (Ftergent)601AD, Forget (Ftergent)602A, Forget (Ftergent) 650-650A, FTX-218 (trade names; Nioos (Neos) Ltd.), Meijiafa (Megafac) F-410, Meijiafa) 430, Jiajiafa (Megac) F-477, Megac-444F-475, Megac-475F-475, Megafac (Megafac) F-552, Megafac (Megafac) F-553, Megafac (Megafac) F-554, Megafac (Megafac) F-555, Megafac (Megafac) F-556, Megafac (Megafac) F-558, Megafac (Megafac) F-559, Megafac (Megafac) R-94, Megafac (Megafac) RS-75, Megafac (Megafac) RS-72-K, Megafac (Megafac) RS-76-NS, Megafac (Megafac) DS-21 (both trade names; Tegason, Tegenison (GmbH) GmbH, Ditut Twinn (TEGO) 4000, Tetwin (Tetwin) 4100, Tediffaro (Tefloford) 370, Tegedo (Tegafac) GmbH (Tegafac) 450, or more, Twy (Tedoni) 450, and Twy (Tandon) (Twy) 450, all, Fluoroalkyl benzenesulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkyl ammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglyceryl tetrakis (fluoroalkyl polyoxyethylene ether), fluoroalkyl trimethylammonium salt, fluoroalkyl sulfamate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, polyoxyethylene tridecyl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, fluoroalkyl iodide, fluoroalkyl betaine, and fluoroalkyl betaine, Polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonate and alkyl diphenyl ether disulfonate. It is preferable to use at least one selected from these surfactants.
Among these surfactants, at least one selected from BYK-306, BYK-342, BYK-346, KP-341, KP-368, Shafu Long (SurfloN) S611, Forgelite (Ftergent)710FL, Forgelite (Ftergent)710FM, Forgelite (Ftergent)710FS, Forgelite (Ftergent)650A, Megafac (Megafac) F-477, Megafac (Megafac) F-556, Megafac (Megafac) RS-72-K, Megafac (Megafac) DS-21, Digo Tun (TEGO TwinN) 4000, fluoroalkylbenzenesulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkyl sulfonate, fluoroalkyl trimethylammonium salt, and fluoroalkyl sulfamate is preferable because the coating uniformity of the thermosetting composition is high.
The content of the surfactant in the thermosetting composition of the present invention is preferably 0.01 to 10 parts by weight based on the total amount of the thermosetting composition.
1-5-4 adhesion improver
From the viewpoint of further improving the adhesion between the formed cured film and the substrate, the thermosetting composition of the present invention may further contain an adhesion improving agent. Examples of the adhesion improver include silane-based, aluminum-based, and titanate-based coupling agents. Specifically, the method comprises the following steps: 3-glycidoxypropyldimethylethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltrimethoxysilane (for example, sala (Sila-Ace) S510; trade name; Jienwis (JNC) Co., Ltd.), silane-based coupling agents such as 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane (e.g., sala-Ace S530; trade name; Jilen (JNC) corporation), 3-mercaptopropyltrimethoxysilane (e.g., sala-Ace S810; trade name; Jilen (JNC) corporation), copolymer of 3-glycidoxypropyltrimethoxysilane (e.g., trade name; Cowensland (COATOSIL) MP200, Japan maiden Performance Materials Japan corporation); aluminum coupling agents such as aluminum acetyl alkoxy diisopropoxide and titanate coupling agents such as tetraisopropyl bis (dioctyl phosphite) titanate.
Among these adhesion improving agents, 3-glycidoxypropyltrimethoxysilane is preferable because it has a large effect of improving adhesion.
The content of the adhesion improver is preferably 0.01 to 10 parts by weight based on the total amount of the thermosetting composition.
1-5-5 antioxidant
The thermosetting composition of the present invention may further contain an antioxidant from the viewpoint of improving transparency and preventing yellowing of the cured film when exposed to high temperatures.
The thermosetting composition of the present invention may contain an antioxidant such as a hindered phenol compound, a hindered amine compound, a phosphorus compound or a sulfur compound. Among them, from the viewpoint of light resistance, hindered phenol-based compounds are preferable. The concrete example is: irganox 1010, Irganox 1010FF, Irganox 1035FF, Irganox 1076FD, Irganox 1078, Irganox 1135, Irganox 1330, Irganox 1726, Irganox 1425, Irganox 1520L, Irganox 245, Irganox 245, Irganox 311259, Irganox 3114, Irganox 565, ADP-E-K-E-ADP-E-P-E-P-E-P-E-P-, Addicotabo (ADK STAB) AO-60 and Addicotabo (ADK STAB) AO-80 (both trade names; Addick (ADEKA) Co., Ltd.). Among them, preferred is xylophilus (Irganox)1010 or Addicusta wave (ADK STAB) AO-60.
The content of the antioxidant is preferably 0.1 to 5 parts by weight based on the total amount of the thermosetting composition.
1-5-6 molecular weight regulator
The thermosetting composition of the present invention may further contain a molecular weight modifier to suppress an increase in molecular weight due to polymerization and to exhibit excellent storage stability. Examples of the molecular weight modifier include: thiols, xanthates, quinones, hydroquinones, and 2, 4-diphenyl-4-methyl-1-pentene.
Specific examples of the molecular weight modifier include: 1, 4-naphthoquinone, 1, 2-benzoquinone, 1, 4-benzoquinone, methyl-p-benzoquinone, anthraquinone, hydroquinone, methylhydroquinone, tert-butylhydroquinone, 2, 5-di-tert-amylhydroquinone, 1, 4-dihydroxynaphthalene, 3, 6-dihydroxybenzonorbornane, 4-methoxyphenol, 2',6,6' -tetra-tert-butyl-4, 4' -dihydroxybiphenyl, stearyl 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, 2' -methylenebis (6-tert-butyl-4-ethylphenol), 2,4, 6-tris (3',5' -di-tert-butyl-4 ' -hydroxybenzyl) mesitylene, pentaerythritol tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], 4-tert-butylcatechol, N-hexylmercaptan, N-octylmercaptan, N-dodecylmercaptan, tert-dodecylmercaptan, thioglycolic acid (thioglycolic acid), dimethyl xanthogen sulfide, diisopropyl xanthogen disulfide, 2, 6-di-tert-butyl-p-cresol, 4 '-butylidenebis (6-tert-butyl-m-cresol), 4' -thiobis (6-tert-butyl-m-cresol), 2, 4-diphenyl-4-methyl-1-pentene, phenothiazine, 2-hydroxy-1, 4-naphthoquinone, and the like.
The molecular weight regulators may be used alone or in combination of two or more. Among the molecular weight regulators, a naphthoquinone-based molecular weight regulator is preferable from the viewpoint of exhibiting excellent storage stability.
Among the molecular weight regulators, 2-hydroxy-1, 4-naphthoquinone having a phenolic hydroxyl group is more preferable from the viewpoint of storage stability.
1-5-7 ultraviolet absorbent
The thermosetting composition of the present invention may contain an ultraviolet absorber from the viewpoint of further improving the deterioration suppressing ability of the formed transparent film.
Specific examples of the ultraviolet absorber are: bin (TINUVIN) P, Bin (TINUVIN)120, Bin (TINUVIN)144, Bin (TINUVIN)213, Bin (TINUVIN)234, Bin (TINUVIN)326, Bin (TINUVIN)571, and Bin (TINUVIN)765 (both trade names; Japanese BASF (Japan) corporation).
The content of the ultraviolet absorber is preferably 0.01 to 10 parts by weight based on the total amount of the thermosetting composition.
1-5-8, anti-coagulating agent
The thermosetting composition of the present invention may contain an anti-coagulating agent from the viewpoint of preventing coagulation of the polyester amic acid (a), the epoxy compound (B), the compound (C) having a polymerizable double bond, and the monofunctional acrylamide compound (D) without fusing them to a solvent.
Specific examples of the anti-agglomerating agent are: dipper (DISPERBYK) -145, Dipper (DISPERBYK) -161, Dipper (DISPERBYK) -162, Dipper (DISPERBYK) -163, Dipper (DISPERBYK) -164, Dipper (DISPERBYK) -182, Dipper (DISPERBYK) -184, Dipper (DISPERBYK) -185, Dipper (DISPERBYK) -2163, Dipper (DISPERBYK) -2164, BYK-220S, Dipper (DISPERBYK) -191, Dipper (DISPERBYK) -199, Dipper (DISPERBYK) -2015 (all trade names; BYK Chemie Japan, Inc.; Floost, Co., Ltd.; Ft-710; all trade names; Floost Co., Ltd.; F-710) .
The content of the anti-coagulation agent is preferably 0.01 to 10 parts by weight based on the total amount of the thermosetting composition.
1-5-9. thermal crosslinking agent
The thermosetting composition of the present invention may contain a thermal crosslinking agent from the viewpoint of further improving heat resistance, chemical resistance, uniformity within the film surface, flexibility, softness, and elasticity.
Specific examples of thermal crosslinkers are: nicarack (Nikalac) MW-30HM, Nicarack (Nikalac) MW-100LM, Nikalac (Nikalac) MX-270, Nikalac (Nikalac) MX-280, Nicarack (Nikalac) MX-290, Nikalac (Nikalac) MW-390 and Nikalac (Nikalac) MW-750LM (both trade names; Sanwa and Chemicals Co., Ltd.).
The content of the thermal crosslinking agent is preferably 0.1 to 10 parts by weight based on the total amount of the thermosetting composition.
1-5-10. other additives
As other components, a styrene-maleic anhydride copolymer may also be added.
1-6 preservation of thermosetting composition
The thermosetting composition of the present invention is preferably stored at-30 to 25 ℃ because the storage stability of the composition is good. When the storage temperature is from-20 ℃ to 10 ℃, precipitates are not generated, and the storage temperature is more preferably from-20 ℃ to 10 ℃.
2. Cured film obtained from thermosetting composition
The thermosetting composition of the present invention can be obtained by: the polyester amic acid (a), the epoxy compound (B), the compound having a polymerizable double bond (C), and the monofunctional acrylamide compound (D) are mixed, and a curing agent, a solvent, a surfactant, an adhesion improver, an antioxidant, and other additives are optionally added according to the desired properties, and these compounds are uniformly mixed and dissolved.
The thermosetting composition prepared in this manner (in the case of a solid state without a solvent, after being dissolved in a solvent) is applied to the surface of a substrate, and the solvent is removed by, for example, heating, whereby a coating film can be formed. The thermosetting composition can be applied to the surface of the substrate by a conventionally known method such as spin coating, roll coating, dipping, slit coating, or the like to form a coating film. Then, the coating film is temporarily calcined by a hot plate, an oven, or the like. The temporary calcination conditions vary depending on the kind and blending ratio of each component, and are usually 70 to 150 ℃,5 to 15 minutes if an oven is used, and 1 to 5 minutes if a hot plate is used. Thereafter, main firing is performed to harden the coating film. The conditions for the main calcination vary depending on the kind and the blending ratio of each component, and the hardened film can be obtained by performing a heat treatment at 180 to 250 ℃, preferably 200 to 250 ℃, for 30 to 90 minutes if an oven is used, or for 5 to 30 minutes if a hot plate is used.
The cured film obtained in this manner is not only excellent in flatness, but also excellent in scratch resistance, transparency, adhesiveness, hygroscopicity, and heat resistance because 1) the polyamic acid of the polyesteramic acid is partially cyclized by dehydration to form an imide bond, 2) the carboxylic acid of the polyesteramic acid is reacted with an epoxy compound to increase the molecular weight, and 3) the epoxy compound is cured to increase the molecular weight, when heated. For the same reason, excellent light resistance, sputtering resistance, scratch resistance, and coatability are also expected. Therefore, the cured film of the present invention is effective as a protective film for a color filter, and a liquid crystal display element or a solid-state imaging element can be manufactured using the color filter. In addition to the protective Film for a color filter, for example, the cured Film of the present invention is effective as a transparent insulating Film formed between a Thin Film Transistor (TFT) and a transparent electrode or between a transparent electrode and an alignment Film. Further, the cured film of the present invention is effective as a protective film for a Light Emitting Diode (LED) Light emitter, for example.
[ examples ]
The present invention will be specifically described with reference to synthesis examples, examples and comparative examples, but the present invention is not limited to these examples.
Hereinafter, the monomer, the polymerization initiator, the chain transfer agent, the solvent, and the like are referred to as follows.
ODPA: 3,3',4,4' -Diphenyl Ether Tetracarboxylic dianhydride
BT-100: 1,2,3, 4-butanetetracarboxylic dianhydride Rikacid BT-100 (trade name; Nissi Susan Co., Ltd.)
DDS: 3,3' -diaminodiphenyl sulfone
SMA 1000P: styrene-maleic anhydride copolymer SMA1000P (trade name; Chuan crude oil Co., Ltd.)
PGMEA: solvent propylene glycol monomethyl ether acetate
PGME: solvent propylene glycol monomethyl ether
MMP: solvent 3-methoxypropionic acid methyl ester
VG 3101L: epoxy Compound TechMORE VG3101L (trade name; PrINTAKE (Printec) Inc.)
NBMA: monofunctional acrylamide Compound N-N-butoxymethylacrylamide (trade name; MCC Unitec, Inc.)
DMAA: monofunctional acrylamide Compound N, N-dimethylacrylamide (trade name; KJ chemical (CHEMICALS) Co., Ltd.)
HEAA: monofunctional acrylamide Compound hydroxyethyl acrylamide (HEAA) (trade name; KJ chemical (CHEMICALS) Co., Ltd.)
IBMA: monofunctional acrylamide Compound N-isobutoxymethacrylamide (trade name; MCC Unitec, Inc.)
DEAA: monofunctional acrylamide Compound Diethylacrylamide (DEAA) (trade name; Kyoho Co., Ltd.)
FAM-301: bifunctional or higher acrylamide Compound FAM-301 (trade name; Fuji film Co., Ltd.)
TMA: curing agent trimellitic anhydride
C11Z: hardener Curezole (Curezole) C11Z (trade name; Shikoku Kagaku Co., Ltd.)
MP 200: cooteosil MP200 (trade name; Momentive Performance Materials Japan, Ltd.) as adhesion improver
AO-60: antioxidant Addicosabo (ADK STAB) AO-60 (trade name; Addicke (ADEKA) Co., Ltd.)
DS-21: surfactant Meijia method (Megafac) DS-21 (trade name; Diegon (DIC) Co., Ltd.)
M-510: aronix M-510 (trade name; Toyo Synthesis Co., Ltd.) as a compound having a polymerizable double bond
First, a polyesteramide acid solution which is a reaction product of tetracarboxylic dianhydride, diamine, monohydroxy compound, polyhydroxy compound, and the like was synthesized in the following manner (see synthesis examples 1 to 2, table 1).
Synthesis example 1 Synthesis of polyesteramic acid (A1)
In a four-necked flask with a stirrer, methyl 3-methoxy propionate (MMP), 3',4,4' -diphenyl ether tetracarboxylic dianhydride (ODPA), 1, 4-butanediol, and benzyl alcohol were charged in the following amounts, and stirred under a dry nitrogen stream at 125 ℃ for 2 hours (first synthesis stage).
Thereafter, the reacted solution was cooled to room temperature, 3' -diaminodiphenyl sulfone (DDS) and MMP were added in the following amounts by weight, and stirred at 20 to 30 ℃ for 2 hours and then at 125 ℃ for 1 hour (second synthesis stage).
DDS 3.26g
MMP 21.00g
[Z/Y=3.0、(Y+Z)/X=0.8]
The solution was cooled to room temperature to obtain a30 wt.% solution of a pale yellow transparent polyester amic acid (A1). A portion of the solution was sampled and weight average molecular weight was determined by GPC analysis (polystyrene standards). As a result, the obtained polyesteramic acid (A1) had a weight-average molecular weight of 4,200.
Synthesis example 2 Synthesis of polyesteramic acid (A2)
In a four-necked flask with a stirrer, Propylene Glycol Monomethyl Ether Acetate (PGMEA), BT-100, SMA1000P, 1, 4-butanediol, and benzyl alcohol, which were subjected to dehydration purification, were charged in this order by the following weight, and stirred under a dry nitrogen flow at 125 ℃ for 2 hours (first stage of synthesis).
Thereafter, the solution after the reaction was cooled to room temperature, DDS and PGMEA were put in the following weight amounts, stirred at 20 to 30 ℃ for 2 hours, and then stirred at 125 ℃ for 1 hour (second synthesis stage).
DDS 1.20g
PGMEA 16.51g
[Z/Y=2.7、(Y+Z)/X=0.9]
The solution was cooled to room temperature to obtain a30 wt.% solution of a pale yellow transparent polyester amic acid (A2). A portion of the solution was sampled and weight average molecular weight was determined by GPC analysis (polystyrene standards). As a result, the obtained polyesteramic acid (A2) had a weight-average molecular weight of 10,000.
Then, using 30 wt% solutions of polyesteramic acid (a1) to polyesteramic acid (a2) obtained in synthesis examples 1 to 2, thermosetting compositions were prepared in the following manner, cured films were obtained from the thermosetting compositions, and the cured films were evaluated.
[ example 1]
A30 wt% solution of polyesteramic acid (A1) obtained in Synthesis example 1, VG3101L, M-510, NBMA, TMA, C11Z, MP200, AO-60, DS-21, MMP, PGMEA, and Propylene Glycol Monomethyl Ether (PGME) were mixed and dissolved in the ratio (unit: g) shown in Table 2-1, and filtered through a membrane filter (0.2 μ M) to obtain a thermosetting composition. Flatness, scratch resistance, transparency, adhesion, moisture absorption, heat resistance and storage stability were evaluated by the methods described below. The results are shown in Table 2-1.
Examples 2 to 13 and comparative examples 1 to 2
The components were mixed and dissolved in the proportions (unit: g) shown in tables 2-1 to 2-2 and 3 by the method of example 1 to obtain a thermosetting composition. The flatness, scratch resistance, transparency, adhesiveness, moisture absorption, heat resistance and storage stability were evaluated by the method of example 1, and the results are shown in tables 2-1 to 2-2 and table 3, respectively.
The total amount of the solvent contained in the thermosetting composition is adjusted so that the total amount of the solvent, MMP and PGMEA contained in the raw material added such as a30 wt% solution of polyesteramic acid (a), and the total amount of the solvent, MMP, PGMEA, and PGME are small, and the solid content concentration in the step becomes approximately 15 wt%.
[ method for evaluating flatness ]
The thermosetting composition was spin-coated at 300rpm for 10 seconds on a color filter substrate having a non-cured film containing R, G, B pixels, the surface level difference of which was measured in advance using a level difference/surface roughness/fine shape measuring apparatus (trade name; P-17, manufactured by Korea Tencor Co., Ltd.), and pre-baked on a heating plate at 90 ℃ for 2 minutes. Then, the resultant was post-baked in an oven at 230 ℃ for 30 minutes to obtain a color filter substrate with a cured film having an average film thickness of the protective film of 1.5 μm. Thereafter, the obtained color filter substrate with the cured film was measured for surface level differences. The flattening ratio (DOP (%)) was calculated from the maximum value of the surface level difference (hereinafter, abbreviated as "maximum level difference") of the color filter substrate without a cured film and the color filter substrate with a cured film by using the following calculation formula. The case where the flattening ratio was 85.0% or more was evaluated as flatness o, and the case where the flattening ratio was less than 85.0% was evaluated as flatness x. Furthermore, the color filter substrate without the cured film has a maximum step of 1.0 μm.
The planarization ratio (DOP (%)) × (maximum step of color filter substrate without cured film-maximum step of color filter substrate with cured film)/(maximum step of color filter substrate without cured film)) × 100
[ method for evaluating scratch resistance ]
The thermosetting composition was spin-coated on a glass substrate at 300rpm for 10 seconds, and pre-baked on a heating plate at 90 ℃ for 2 minutes. The glass substrate with the cured film was post-baked in an oven at 230 ℃ for 30 minutes to obtain a film thickness of 1.5. mu.m. The obtained glass substrate with a cured film was subjected to 8.4.1 pencil scratch test of Japanese Industrial Standards (JIS) K-5400-1990 to thereby measure the pencil hardness of the cured film. The case where the pencil hardness was 3H or more was evaluated as "scratch resistance", and the case where the pencil hardness was 2H or less was evaluated as "scratch resistance".
[ method for evaluating transparency ]
The thermosetting composition was spin-coated on a glass substrate at 300rpm for 10 seconds, and pre-baked on a heating plate at 90 ℃ for 2 minutes. The glass substrate with the cured film was post-baked in an oven at 230 ℃ for 30 minutes to obtain a film thickness of 1.5. mu.m. The transmittance of the cured film was measured with an ultraviolet-visible spectrophotometer on the obtained glass substrate with the cured film. The transmittance at a wavelength of 400nm was 95.0% or more, and the transmittance was evaluated as "transparency".
[ method for evaluating adhesion ]
The thermosetting composition was spin-coated on a glass substrate at 300rpm for 10 seconds, and pre-baked on a heating plate at 90 ℃ for 2 minutes. The glass substrate with the cured film was post-baked in an oven at 230 ℃ for 30 minutes to obtain a film thickness of 1.5. mu.m. The obtained glass substrate with the hardened film was tested according to International Organization for Standardization (ISO) 2409. The test results were rated as "o" when the adhesion between class 0 and class 1 was shown, and rated as "x" when the adhesion between class 2 and class 5 was shown.
[ method for evaluating moisture absorption ]
The thermosetting composition was spin-coated on a glass substrate at 300rpm for 10 seconds, and pre-baked on a heating plate at 90 ℃ for 2 minutes. The glass substrate with the cured film was post-baked in an oven at 230 ℃ for 30 minutes to obtain a film thickness of 1.5. mu.m. The obtained cured film was cut into powder, and the weight change before and after heating was measured by a thermogravimetric differential thermal analyzer. At this time, in the thermogravimetric differential thermal analyzer test, the temperature was raised from room temperature to 150 ℃ at 10 ℃/min and heated at 150 ℃ for 20 minutes. The weight at the time of starting the temperature increase from room temperature to 150 ℃ was defined as the weight before heating, the weight after heating at 150 ℃ for 20 minutes was defined as the weight after heating, and the weight loss was calculated using the following formula. The case where the weight loss amount was 2.0% or less was regarded as "o", and the case where the weight loss amount was more than 2.0% was regarded as "x".
Weight loss (wt%) ((weight after heating-weight before heating)/(weight before heating)) × 100
[ method for evaluating Heat resistance ]
The thermosetting composition was spin-coated on a glass substrate at 300rpm for 10 seconds, and pre-baked on a heating plate at 90 ℃ for 2 minutes. The glass substrate with the cured film was post-baked in an oven at 230 ℃ for 30 minutes to obtain a film thickness of 1.5. mu.m. The obtained cured film was cut into powder, and the weight change before and after heating was measured by a thermogravimetric differential thermal analyzer. At this time, in the thermogravimetric differential thermal analyzer test, the temperature was raised from room temperature to 150 ℃ at 10 ℃/min and heated at 150 ℃ for 20 minutes, and then, the temperature was raised from 150 ℃ to 250 ℃ at 10 ℃/min and heated at 250 ℃ for 30 minutes. The weight at the time of starting the temperature increase from 150 ℃ to 250 ℃ was defined as the weight before heating, the weight after heating at 250 ℃ for 30 minutes was defined as the weight after heating, and the weight loss amount was calculated using the following formula. The case where the weight loss amount was 3.0% or less was indicated by ∘, and the case where the weight loss amount was more than 3.0% was indicated by x.
Weight loss (wt%) ((weight after heating-weight before heating)/(weight before heating)) × 100
[ evaluation method of storage stability ]
32mL of the thermosetting composition was prepared, and 16mL of the composition was collected to measure the viscosity. The viscosity at this time was taken as the initial viscosity. Then, the remaining 16mL of the thermosetting composition was poured into a20 mL glass container, and the lid was closed after blowing nitrogen gas, and the lid was sealed with a paraffin film. The mixture was placed in a constant temperature and humidity bath (conditions: 40 ℃ C., humidity 60%) and allowed to stand for 3 weeks. After standing, the sample was removed and the viscosity was measured. The viscosity change rate was calculated using the following formula. With reference to the initial viscosity, the value of the viscosity change rate after 3 weeks was 20% or less was defined as "o", and the value of the viscosity change rate exceeding 20% was defined as "x".
Viscosity change rate (%) ((viscosity after standing-initial viscosity)/(initial viscosity)) × 100
As is clear from the results shown in tables 2-1 to 2-2: the thermosetting compositions of examples 1 to 13 have excellent flatness and also satisfy other properties required for thermosetting compositions. On the other hand, as is clear from the results shown in table 3: comparative example 1 and comparative example 2 do not satisfy one or more of these characteristics.
[ industrial applicability ]
The cured film formed using the thermosetting composition of the present invention has high flatness and excellent scratch resistance, transparency, adhesiveness, moisture absorption and heat resistance, and is useful as a protective film for a color filter. In addition, the film can be used as an insulating film, a passivation film, a buffer coating film, or a planarization film of various electronic parts.
Claims (7)
1. A thermosetting composition comprising a polyester amic acid (A), an epoxy compound (B), a compound (C) having a polymerizable double bond, and a monofunctional acrylamide compound (D), characterized in that,
the polyesteramic acid (A) is a reaction product of raw materials comprising X moles of a tetracarboxylic dianhydride, Y moles of a diamine and Z moles of a polyhydric hydroxyl compound at a ratio satisfying the relationship of the following formulas (1) and (2);
0.2≦Z/Y≦8.0·······(1)
0.2≦(Y+Z)/X≦5.0···(2)。
2. the thermosetting composition according to claim 1, wherein the polyesteramic acid (A) comprises a structural unit represented by the following formula (3) and a structural unit represented by the following formula (4);
in the formulae (3) and (4), R1Is a structure obtained by removing two groups-C (═ O) -O-C (═ O) -from a tetracarboxylic acid dianhydride, R is2For removing two-NH groups from diamines2To a structure of R3Is a structure obtained by removing two-OH groups from a polyvalent hydroxyl compound.
3. The thermosetting composition according to claim 1 or 2, wherein the compound (C) having a polymerizable double bond is a compound having three or more (meth) acryloyl groups per molecule.
4. The thermosetting composition according to any one of claims 1 to 3, wherein the content of the epoxy compound (B) is 20 to 400 parts by weight based on 100 parts by weight of the polyester amic acid (A), the content of the compound (C) having a polymerizable double bond is 1 to 200 parts by weight based on 100 parts by weight of the polyester amic acid (A), and the content of the monofunctional acrylamide compound (D) is 41 to 200 parts by weight based on 100 parts by weight of the polyester amic acid (A).
5. The thermosetting composition according to any one of claims 1 to 3, wherein the content of the epoxy compound (B) is 20 to 400 parts by weight based on 100 parts by weight of the polyester amic acid (A), the content of the compound (C) having a polymerizable double bond is 1 to 200 parts by weight based on 100 parts by weight of the polyester amic acid (A), and the content of the monofunctional acrylamide compound (D) is 50 to 150 parts by weight based on 100 parts by weight of the polyester amic acid (A).
6. A cured film obtained by curing the thermosetting composition according to any one of claims 1 to 5.
7. A color filter having the cured film according to claim 6 as a transparent protective film.
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Publication number | Priority date | Publication date | Assignee | Title |
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TW200909521A (en) * | 2007-07-27 | 2009-03-01 | Chisso Corp | Composition comprising polyester amide acid and ink-jet composition using the composition |
CN105408417A (en) * | 2013-07-25 | 2016-03-16 | 捷恩智株式会社 | Thermosetting resin composition, cured film, substrate with curing film, and electronic component |
WO2018159675A1 (en) * | 2017-03-02 | 2018-09-07 | Jnc株式会社 | Thermosetting resin composition, cured film, substrate having cured film, electronic component, and ink composition for inkjet |
CN109423192A (en) * | 2017-08-30 | 2019-03-05 | 捷恩智株式会社 | Thermosetting composition, cured film and colored filter |
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Publication number | Priority date | Publication date | Assignee | Title |
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TW200909521A (en) * | 2007-07-27 | 2009-03-01 | Chisso Corp | Composition comprising polyester amide acid and ink-jet composition using the composition |
CN105408417A (en) * | 2013-07-25 | 2016-03-16 | 捷恩智株式会社 | Thermosetting resin composition, cured film, substrate with curing film, and electronic component |
WO2018159675A1 (en) * | 2017-03-02 | 2018-09-07 | Jnc株式会社 | Thermosetting resin composition, cured film, substrate having cured film, electronic component, and ink composition for inkjet |
TW201839052A (en) * | 2017-03-02 | 2018-11-01 | 日商捷恩智股份有限公司 | Thermosetting resin composition, cured film, substrate having cured film, electronic component, and ink composition for inkjet |
CN109423192A (en) * | 2017-08-30 | 2019-03-05 | 捷恩智株式会社 | Thermosetting composition, cured film and colored filter |
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