CN117069942A - Polysiloxane compound, composition for forming film, laminate, touch panel, and method for forming cured film - Google Patents
Polysiloxane compound, composition for forming film, laminate, touch panel, and method for forming cured film Download PDFInfo
- Publication number
- CN117069942A CN117069942A CN202310418938.4A CN202310418938A CN117069942A CN 117069942 A CN117069942 A CN 117069942A CN 202310418938 A CN202310418938 A CN 202310418938A CN 117069942 A CN117069942 A CN 117069942A
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- CN
- China
- Prior art keywords
- film
- structural unit
- compound
- polysiloxane
- silane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 Polysiloxane Polymers 0.000 title claims abstract description 136
- 150000001875 compounds Chemical class 0.000 title claims abstract description 115
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 97
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 238000000034 method Methods 0.000 title claims description 18
- 229910000077 silane Inorganic materials 0.000 claims abstract description 56
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 8
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims abstract description 8
- 239000011248 coating agent Substances 0.000 claims description 26
- 238000000576 coating method Methods 0.000 claims description 26
- 239000003960 organic solvent Substances 0.000 claims description 17
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 14
- 239000007870 radical polymerization initiator Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 8
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 7
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 150000004756 silanes Chemical class 0.000 abstract description 6
- 238000012360 testing method Methods 0.000 description 45
- 238000011156 evaluation Methods 0.000 description 38
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- 239000000758 substrate Substances 0.000 description 20
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 12
- 238000004090 dissolution Methods 0.000 description 11
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 11
- 210000003811 finger Anatomy 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 238000000206 photolithography Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- RLUCXJBHKHIDSP-UHFFFAOYSA-N propane-1,2-diol;propanoic acid Chemical compound CCC(O)=O.CC(O)CO RLUCXJBHKHIDSP-UHFFFAOYSA-N 0.000 description 6
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000002685 polymerization catalyst Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 3
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 3
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 3
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 3
- MWGRRMQNSQNFID-UHFFFAOYSA-N 1-(2-methylpropoxy)propan-2-ol Chemical compound CC(C)COCC(C)O MWGRRMQNSQNFID-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 2
- LEDYRHPAPPWTNW-UHFFFAOYSA-N 2-(2-propan-2-yloxypropoxy)propyl acetate Chemical compound C(C)(=O)OCC(OCC(C)OC(C)C)C LEDYRHPAPPWTNW-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ATGKAFZFOALBOF-UHFFFAOYSA-N cyclohexyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C1CCCCC1 ATGKAFZFOALBOF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- MGQFVQQCNPBJKC-UHFFFAOYSA-N dibutoxy(diethyl)silane Chemical compound CCCCO[Si](CC)(CC)OCCCC MGQFVQQCNPBJKC-UHFFFAOYSA-N 0.000 description 2
- GQNWJCQWBFHQAO-UHFFFAOYSA-N dibutoxy(dimethyl)silane Chemical compound CCCCO[Si](C)(C)OCCCC GQNWJCQWBFHQAO-UHFFFAOYSA-N 0.000 description 2
- IMSOLVFQJWOSCD-UHFFFAOYSA-N dibutyl-bis(2-methylpropoxy)silane Chemical compound CCCC[Si](CCCC)(OCC(C)C)OCC(C)C IMSOLVFQJWOSCD-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
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- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- IZRJPHXTEXTLHY-UHFFFAOYSA-N triethoxy(2-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC[Si](OCC)(OCC)OCC IZRJPHXTEXTLHY-UHFFFAOYSA-N 0.000 description 2
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 2
- NIINUVYELHEORX-UHFFFAOYSA-N triethoxy(triethoxysilylmethyl)silane Chemical compound CCO[Si](OCC)(OCC)C[Si](OCC)(OCC)OCC NIINUVYELHEORX-UHFFFAOYSA-N 0.000 description 2
- 229940083957 1,2-butanediol Drugs 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
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- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000004005 nitrosamines Chemical class 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
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- FABOKLHQXVRECE-UHFFFAOYSA-N phenyl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1 FABOKLHQXVRECE-UHFFFAOYSA-N 0.000 description 1
- VPLNCHFJAOKWBT-UHFFFAOYSA-N phenyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C1=CC=CC=C1 VPLNCHFJAOKWBT-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- DNAJDTIOMGISDS-UHFFFAOYSA-N prop-2-enylsilane Chemical class [SiH3]CC=C DNAJDTIOMGISDS-UHFFFAOYSA-N 0.000 description 1
- SZEGZMUSBCXNLO-UHFFFAOYSA-N propan-2-yl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)C(C)C SZEGZMUSBCXNLO-UHFFFAOYSA-N 0.000 description 1
- YHNFWGSEMSWPBF-UHFFFAOYSA-N propan-2-yl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C(C)C YHNFWGSEMSWPBF-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
- UIDUKLCLJMXFEO-UHFFFAOYSA-N propylsilane Chemical class CCC[SiH3] UIDUKLCLJMXFEO-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003566 sealing material Substances 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
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- FJYXLOSYDKUABM-UHFFFAOYSA-N tri(butan-2-yloxy)-cyclohexylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1CCCCC1 FJYXLOSYDKUABM-UHFFFAOYSA-N 0.000 description 1
- MHQDJCZAQGWXBC-UHFFFAOYSA-N tri(butan-2-yloxy)-ethenylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C=C MHQDJCZAQGWXBC-UHFFFAOYSA-N 0.000 description 1
- PCDRXIBYKFIRQR-UHFFFAOYSA-N tri(butan-2-yloxy)-phenylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC=C1 PCDRXIBYKFIRQR-UHFFFAOYSA-N 0.000 description 1
- QSQGFMKPTBYFTM-UHFFFAOYSA-N tri(butan-2-yloxy)-propan-2-ylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C(C)C QSQGFMKPTBYFTM-UHFFFAOYSA-N 0.000 description 1
- ZARIZDBUWOPYMT-UHFFFAOYSA-N tri(butan-2-yloxy)-propylsilane Chemical compound CCC(C)O[Si](CCC)(OC(C)CC)OC(C)CC ZARIZDBUWOPYMT-UHFFFAOYSA-N 0.000 description 1
- MQVCTPXBBSKLFS-UHFFFAOYSA-N tri(propan-2-yloxy)-propylsilane Chemical compound CCC[Si](OC(C)C)(OC(C)C)OC(C)C MQVCTPXBBSKLFS-UHFFFAOYSA-N 0.000 description 1
- XCQYKITYUMPINW-UHFFFAOYSA-N tributoxy(cyclohexyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1CCCCC1 XCQYKITYUMPINW-UHFFFAOYSA-N 0.000 description 1
- ZNSNSQWRWNCUMB-UHFFFAOYSA-N tributoxy(cyclopentyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1CCCC1 ZNSNSQWRWNCUMB-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- LEZQEMOONYYJBM-UHFFFAOYSA-N tributoxy(propan-2-yl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C(C)C LEZQEMOONYYJBM-UHFFFAOYSA-N 0.000 description 1
- WAAWAIHPWOJHJJ-UHFFFAOYSA-N tributoxy(propyl)silane Chemical compound CCCCO[Si](CCC)(OCCCC)OCCCC WAAWAIHPWOJHJJ-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- BJDLPDPRMYAOCM-UHFFFAOYSA-N triethoxy(propan-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)C BJDLPDPRMYAOCM-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- QYBKVVRRGQSGDC-UHFFFAOYSA-N triethyl methyl silicate Chemical compound CCO[Si](OC)(OCC)OCC QYBKVVRRGQSGDC-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JCGDCINCKDQXDX-UHFFFAOYSA-N trimethoxy(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](OC)(OC)OC JCGDCINCKDQXDX-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- LGROXJWYRXANBB-UHFFFAOYSA-N trimethoxy(propan-2-yl)silane Chemical compound CO[Si](OC)(OC)C(C)C LGROXJWYRXANBB-UHFFFAOYSA-N 0.000 description 1
- DJYGUVIGOGFJOF-UHFFFAOYSA-N trimethoxy(trimethoxysilylmethyl)silane Chemical compound CO[Si](OC)(OC)C[Si](OC)(OC)OC DJYGUVIGOGFJOF-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- PJEMIBXFOHYKMS-UHFFFAOYSA-N tris(2-methylpropoxy)-phenylsilane Chemical compound CC(C)CO[Si](OCC(C)C)(OCC(C)C)C1=CC=CC=C1 PJEMIBXFOHYKMS-UHFFFAOYSA-N 0.000 description 1
- MOGQHPIOEFLJQH-UHFFFAOYSA-N tris(2-methylpropoxy)-propan-2-ylsilane Chemical compound CC(C)CO[Si](OCC(C)C)(OCC(C)C)C(C)C MOGQHPIOEFLJQH-UHFFFAOYSA-N 0.000 description 1
- POQYUENPWRRXNK-UHFFFAOYSA-N tris(2-methylpropoxy)-propylsilane Chemical compound CC(C)CO[Si](CCC)(OCC(C)C)OCC(C)C POQYUENPWRRXNK-UHFFFAOYSA-N 0.000 description 1
- KGOOITCIBGXHJO-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-phenylsilane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1 KGOOITCIBGXHJO-UHFFFAOYSA-N 0.000 description 1
- MJIHPVLPZKWFBL-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propan-2-ylsilane Chemical compound CC(C)(C)O[Si](C(C)C)(OC(C)(C)C)OC(C)(C)C MJIHPVLPZKWFBL-UHFFFAOYSA-N 0.000 description 1
- DIZPPYBTFPZSGK-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propylsilane Chemical compound CCC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C DIZPPYBTFPZSGK-UHFFFAOYSA-N 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G06—COMPUTING; CALCULATING OR COUNTING
- G06F—ELECTRIC DIGITAL DATA PROCESSING
- G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
- G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
- G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
- G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Theoretical Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Wood Science & Technology (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Human Computer Interaction (AREA)
- Materials For Photolithography (AREA)
- Silicon Polymers (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
Provided is a polysiloxane compound from which a cured film having excellent adhesion can be obtained, and which has excellent developability and photocurability. The polysiloxane compound at least comprises: structural units (A) derived from at least one silane compound (A) selected from the group consisting of tetraalkoxysilanes and bis (trialkoxysilyl) alkanes, structural units (B) derived from at least one silane compound (B) selected from the group consisting of alkyltrialkoxysilanes, dialkyldialkoxysilanes, cycloalkyltrialkoxysilanes, vinyltrialkoxysilanes, phenyltrialkoxysilanes, and structural units (C) derived from silane compounds (C) having radically polymerizable unsaturated double bonds. The composition ratio of the polysiloxane compound calculated by the following formula (1) is more than 0 and less than 0.1, (MC)/(MA+MB) (1). In the formula (1), MA represents the number of moles of the structural unit (a), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).
Description
Cross-reference to related application the present application claims priority to the application patent application "japanese patent application 2022-080415" filed in japan patent office at month 05 and 16 of 2022, and the disclosure of this application is incorporated herein in its entirety into the present specification.
Technical Field
The present application relates to a polysiloxane compound, a film-forming composition, a laminate, a touch panel, and a method for forming a cured film.
Background
Silicone compounds are used as a film-forming composition for forming an insulating layer for use in a touch panel (touch panel), a sensor portion of an electronic component such as an LED, a semiconductor, or the like used in a smart phone or a tablet Personal Computer (PC).
For example, patent document 1 discloses a resin composition for a white LED sealing material, which contains 0.5 to 10 parts by mass of a radical initiator per 100 parts by mass of polysiloxane having a (meth) acryloyl group.
The polysiloxane compound has adhesion after prebaking, and when used in a touch panel or the like, the polysiloxane compound causes adhesion of a substrate and a mask during contact exposure, and has a problem of poor operability during processing.
On the other hand, although a proximity exposure method in which a gap is provided so as not to damage the substrate and the mask is used, there is a disadvantage in that the resolution is lowered due to the gap.
In the method described in patent document 1, the adhesion (adhesion-inhibiting property) is insufficient, and there is room for further improvement.
In addition, photolithography is mainly used for forming an electrode layer or an insulating layer used for an electronic component or the like.
Therefore, in the developing step, it is necessary to have a property (also referred to as photocurability) that the exposed portion irradiated with the active energy ray is not removed by the developer; on the other hand, the unexposed portion that shields the active energy rays is rapidly dissolved and removed by the developer (also referred to as developability).
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2008-131009
Disclosure of Invention
Technical problem to be solved by the invention
Accordingly, an object of the present invention is to provide a polysiloxane compound from which a cured film excellent in adhesion can be obtained, and which is excellent in developability and photocurability.
Means for solving the problems
As a result of intensive studies on silicone compounds, the present inventors have found that a silicone compound which can solve the above-mentioned problems comprehensively can be obtained by having structural units derived from a specific silicone compound in a predetermined molar ratio.
That is, the present invention is a polysiloxane compound comprising at least a structural unit (a), a structural unit (B) and a structural unit (C); the structural unit (a) is derived from a silane-based compound (a) selected from at least one of the group consisting of tetraalkoxysilane and bis (trialkoxysilyl) alkane; the structural unit (B) is derived from a silane compound (B) selected from at least one of the group consisting of alkyl trialkoxysilane, dialkyl dialkoxysilane, cycloalkyl trialkoxysilane, vinyl trialkoxysilane and phenyl trialkoxysilane; the structural unit (C) is derived from a silane compound (C) having a radically polymerizable unsaturated double bond. The composition ratio of the polysiloxane compound calculated by the following formula (1) is more than 0 and less than 0.1,
in the formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).
In the polysiloxane compound of the present invention, the silane compound (a) is preferably tetraethoxysilane.
The silane compound (B) is preferably phenyltrimethoxysilane and/or methyltriethoxysilane.
The silane compound (C) is preferably 3- (methacryloyloxy) propyltrimethoxysilane.
The composition ratio calculated from the above formula (1) is preferably 0.03 or more and 0.08 or less.
The present invention also relates to a film-forming composition comprising at least the polysiloxane compound, a photoradical polymerization initiator, and an organic solvent.
In the film-forming composition of the present invention, the photoradical polymerization initiator preferably contains a ketoxime ester group.
The present invention also relates to a laminate obtained by applying the film-forming composition.
The present invention also relates to a touch panel using the laminate.
The present invention also relates to a method for forming a cured coating, comprising: a coating step of coating the film-forming composition; an exposure step of irradiating an exposure portion with an active energy ray to form a cured film; and a developing step of dissolving and removing the coating liquid of the unexposed portion with a developing liquid.
Effects of the invention
Provided is a polysiloxane compound from which a cured film having excellent adhesion can be obtained, and which has excellent developability and photocurability.
Detailed Description
< Silicone-based Compounds >
The polysiloxane compound at least comprises a structural unit (A), a structural unit (B) and a structural unit (C); the structural unit (a) is derived from a silane-based compound (a) selected from at least one of the group consisting of tetraalkoxysilane and bis (trialkoxysilyl) alkane; the structural unit (B) is derived from a silane compound (B) selected from at least one of the group consisting of alkyl trialkoxysilane, dialkyl dialkoxysilane, cycloalkyl trialkoxysilane, vinyl trialkoxysilane and phenyl trialkoxysilane; the structural unit (C) is derived from a silane compound (C) having a radically polymerizable unsaturated double bond. The composition ratio of the polysiloxane compound calculated by the following formula (1) is more than 0 and less than 0.1,
in the formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).
[ silane-based Compound (A) ]
The polysiloxane compound of the present invention contains a structural unit (a) derived from a silane compound (a) which is at least one selected from the group consisting of tetraalkoxysilanes and bis (trialkoxysilyl) alkanes.
The silane compound (a) is at least one selected from the group consisting of tetraalkoxysilanes and bis (trialkoxysilyl) alkanes.
Examples of the tetraalkoxysilane include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, tetraisobutoxysilane, ethoxytrimethoxysilane, dimethoxydiethoxysilane, and methoxytriethoxysilane.
Examples of the bis (trialkoxysilyl) alkane include bis (trimethoxysilyl) methane, bis (triethoxysilyl) methane, 1, 2-bis (trimethoxysilyl) ethane, and 1, 2-bis (triethoxysilyl) ethane.
The silane compound (a) is preferably tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetraisopropoxysilane, tetra-n-butoxysilane, tetraisobutoxysilane, bis (triethoxysilyl) methane, or 1, 2-bis (triethoxysilyl) ethane, more preferably tetramethoxysilane, tetraethoxysilane, or tetraisopropoxysilane, and still more preferably tetraethoxysilane, from the viewpoint of versatility.
[ silane-based Compound (B) ]
The polysiloxane compound of the present invention comprises a structural unit (B), wherein the structural unit (B) is derived from a silane compound (B) selected from at least one of the group consisting of an alkyl trialkoxysilane, a dialkyl dialkoxysilane, a cycloalkyl trialkoxysilane, a vinyl trialkoxysilane, and a phenyl trialkoxysilane.
Examples of the alkyl trialkoxysilane include methyltrimethoxysilane, methyltriethoxysilane, methyltrispanoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, ethyltri-n-propoxysilane, ethyltriisopropoxysilane, ethyltri-n-butoxysilane, ethyltriisobutoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, n-propyltri-n-propoxysilane, n-propyltriisopropoxysilane, n-propyltri-n-butoxysilane, n-propyltriisobutoxysilane, n-propyltri-sec-butoxysilane, n-propyltri-tert-butoxysilane, isopropyltrimethoxysilane, isopropyltriethoxysilane, isopropyltri-n-propoxysilane, isopropyltriisopropoxysilane, isopropyltri-n-butoxysilane, isopropyltriisobutoxysilane, isopropyltri-sec-butoxysilane, and isopropyltri-tert-butoxysilane.
Examples of the dialkyldialkoxysilane include dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldi-n-propoxysilane, dimethyldiisopropyloxysilane, dimethyldi-n-butoxysilane, dimethyldiisobutoxysilane, dimethyldi-n-butoxysilane, dimethyldi-n-propyldi-n-butoxysilane, dimethyldi-sec-butoxysilane, dimethyldi-tert-butoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diethyldi-n-propoxysilane, diethyldiisopropyloxysilane, diethyldi-n-butoxysilane, diethyldi-sec-butoxysilane, diethyldi-n-butoxysilane, diethyldi-tert-butoxysilane, diethyldi-n-propyldimethoxysilane, di-n-propyldiethoxysilane, di-n-propyldi-n-propoxysilane, di-n-propyldi-isopropoxysilane, di-n-propyldi-n-butoxysilane, di-n-propyldi-sec-butoxysilane, di-n-butyldi-isobutoxysilane, di-n-butyldi-n-isobutoxysilane, di-n-butyldi-isobutoxysilane, diisobutyldi-n-butoxysilane, diisobutyldiisobutoxysilane, diisobutyldi-sec-butoxysilane, diisobutyldi-t-butoxysilane, di-sec-butyldimethoxysilane, di-sec-butyldiethoxysilane, di-sec-di-n-propoxysilane, di-sec-butyldiisopropoxysilane, di-sec-di-n-butoxysilane, di-sec-butyldiisobutoxysilane, di-sec-butyldi-sec-butoxysilane, di-sec-butyldi-t-butoxysilane, di-t-butyldimethoxysilane, di-t-butyldiethoxysilane, di-t-butyldi-n-propoxysilane, di-t-butyldi-i-propoxysilane, di-t-butyldi-sec-butoxysilane, di-t-butyldi-t-butoxysilane, and the like.
Examples of the cycloalkyl trialkoxysilane include cyclopentyl trimethoxysilane, cyclopentyl triethoxysilane, cyclopentyl tri-n-propoxysilane, cyclopentyl triisopropoxysilane, cyclopentyl tri-n-butoxysilane, cyclopentyl triisobutoxysilane, cyclopentyl tri-sec-butoxysilane, cyclohexyl trimethoxysilane, cyclohexyl triethoxysilane, cyclohexyl tri-n-propoxysilane, cyclohexyl triisopropoxysilane, cyclohexyl tri-n-butoxysilane, cyclohexyl triisobutoxysilane, cyclohexyl tri-sec-butoxysilane, and cyclohexyl tri-tert-butoxysilane.
Examples of the vinyltrialkoxysilane include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri-n-propoxysilane, vinyltriisopropoxysilane, vinyltri-n-butoxysilane, vinyltriisobutoxysilane, vinyltri-sec-butoxysilane, and vinyltri-tert-butoxysilane.
Examples of the phenyltrialkoxysilane include phenyltrimethoxysilane, phenyltriethoxysilane, phenyltri-n-propoxysilane, phenyltriisopropoxysilane, phenyltri-n-butoxysilane, phenyltriisobutoxysilane, phenyltri-sec-butoxysilane, and phenyltri-tert-butoxysilane.
The silane compound (B) is preferably at least one selected from methyltriethoxysilane, dimethyldimethoxysilane, cyclohexyltriethoxysilane, vinyltrimethoxysilane and phenyltrimethoxysilane, and more preferably phenyltrimethoxysilane and/or methyltriethoxysilane.
[ silane Compound (C) ]
The polysiloxane compound of the present invention comprises at least a structural unit (C) derived from a silane compound (C) having a radically polymerizable unsaturated double bond.
Examples of the silane compound (C) include [3- (meth) acryloyloxy ] propyl silane compounds such as [3- (meth) acryloyloxy ] propyl methyldimethoxysilane, [3- (meth) acryloyloxy ] propyl trimethoxysilane, [3- (meth) acryloyloxy ] propyl ethyldiethoxysilane, [3- (meth) acryloyloxy ] propyl triethoxysilane, and allyl silane compounds such as allyl trimethoxysilane and allyl triethoxysilane.
Among them, from the viewpoint of balance between developability and stability of maintaining the pattern shape of the cured film, [3- (meth) acryloyloxy ] propyl trimethoxysilane is preferable.
[ other silane-based Compound (D) ]
As the silane compound before condensation constituting the polysiloxane compound, a silane compound having an epoxy group in the molecule, for example, may be added as needed.
Examples of the silane compound having an epoxy group in the molecule include (3-glycidoxypropyl) trimethoxysilane, (3-glycidoxypropyl) methyldimethoxysilane, (3-glycidoxypropyl) triethoxysilane, (3-glycidoxypropyl) methyldiethoxysilane, 2- (3, 4-epoxycyclohexane) ethyltrimethoxysilane, [2- (3, 4-epoxycyclohexane) ethyl ] triethoxysilane, [2- (3, 4-epoxycyclohexane) ethyl ] methyldimethoxysilane, [2- (3, 4-epoxycyclohexane) ethyl ] methyldiethoxysilane, and the like.
[ composition ratio ]
The composition ratio of the polysiloxane compound of the present invention calculated by the following formula (1) is more than 0 and less than 0.1.
By setting the composition ratio in the above range, the adhesion of the cured film can be suppressed, and a polysiloxane compound excellent in developability and photocurability can be obtained.
The composition ratio calculated from the following formula (1) is preferably 0.03 or more and 0.08 or less.
In the formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).
The molar ratio of the structural unit (a) derived from the silane compound (a) to the entire (total) structural units forming the polysiloxane compound is preferably 0.10 to 0.25, more preferably 0.15 to 0.22, from the viewpoint of improving the developability of the non-photocured portions of the unexposed portions and the photocured portions of the exposed portions when the film-forming composition of the present invention is applied by photolithography to form a cured film.
The molar ratio of the structural unit (B) derived from the silane compound (B) to the entire (total) structural units forming the polysiloxane compound is preferably 0.65 to 0.90, more preferably 0.70 to 0.85, from the viewpoint of improving the developability of the non-photocured portions of the unexposed portions and the photocured portions of the exposed portions when the film-forming composition of the present invention is applied by photolithography to form a cured film.
From the viewpoints of photocurability and adhesion, the molar ratio of the structural unit (C) derived from the silane compound (C) to the entire structural unit forming the polysiloxane compound is preferably 0.020 to 0.10, more preferably 0.025 to 0.075.
From the viewpoints of developability of the non-light-cured portion of the unexposed portion and adhesion between the cured film and the substrate or ITO electrode, the molar ratio of the structural unit (D) derived from the silane compound (D) to the entire structural unit forming the polysiloxane compound is preferably 0 to 0.005, more preferably 0 to 0.002.
[ method for producing polysiloxane Compound ]
The method for producing the polysiloxane compound will be described.
As a method for producing the polysiloxane compound, for example, the following method can be used: and a method in which the silane compounds (a) to (C) and optionally other silane compounds (D) are mixed in a suitable container, water and a polymerization catalyst are added, and if necessary, a reaction solvent is added to hydrolyze and condense the mixture.
The amount of water is preferably an amount such that the molecular number of water is the same as the number of all hydrolyzable substituents of the silane compound placed in the container.
Since the silane compound has 3 or 4 hydrolyzable substituents on average in one molecule, when such a silane compound is contained in a large amount, the amount of water can be easily set to an amount such that the number of water molecules becomes 3 to 4 times (as a molar ratio, the total amount of silane compounds: water=1:3 to 1:4) the total number of molecules of the silane compound to be contained in the container.
As the polymerization catalyst, for example, it is possible to use: acid catalysts such as acetic acid and hydrochloric acid, and base catalysts such as ammonia, triethylamine, cyclohexylamine, tetramethylammonium hydroxide, and the like. The amount of the polymerization catalyst is preferably an amount such that the molecular weight of the polymerization catalyst is 0.05 to 0.2 times (molar ratio, total amount of the silane compound: polymerization catalyst=1:0.05 to 1:0.2) the total molecular weight of the silane compound placed in the container.
The reaction solvent is preferably: lower alcohols such as ethanol, n-propanol and isopropanol, ketone compounds such as acetone and methyl ethyl ketone, and ester compounds such as ethyl acetate and n-propyl acetate. Among them, lower alcohols are more preferable; ethanol and isopropanol are more preferable from the viewpoint of being able to maintain an appropriate reaction temperature and being easily distilled off.
The reaction temperature is preferably 60 to 80℃and the reaction time is preferably about 2 to 24 hours to allow the reaction to proceed sufficiently.
After the reaction, the undesired by-products other than the above-mentioned polysiloxane compound may be removed by extraction, dehydration, solvent removal, or the like, to obtain the above-mentioned polysiloxane compound.
[ physical Properties of Silicone-based Compounds ]
The polysiloxane compound of the present invention has excellent adhesion (can inhibit adhesion).
Regarding the above adhesion, it can be judged by the following test.
The polysiloxane compound was diluted with propylene glycol monomethyl acetate so that the concentration of the nonvolatile component became 25 mass%, and the polysiloxane compound was applied to a commercially available 50mm square sodium glass substrate under an application condition of 400rpm for 60 seconds using a spin coater (MS-a 100, manufactured by MIKASA co., LTD).
Subsequently, the test piece for evaluation was prepared by heating (prebaking) at 80℃for 3 minutes.
The surface of the evaluation test piece coated with the polysiloxane compound was touched with a finger to visually confirm the extent of trace remaining, and if no trace was found by the finger, it was judged that the adhesion was excellent.
The polysiloxane compound of the present invention has excellent developability.
The developability can be determined by the following test.
The test piece for evaluation used in the adhesion test was exposed to a 2.38 mass% aqueous solution of tetramethylammonium hydroxide (developing solution), and when the dissolution state was visually observed, it was confirmed that the developing property was excellent.
The polysiloxane compound of the present invention has excellent photocurability.
The above photocurability can be determined by the following test.
2.5 parts by mass of Irgacure OXE02, 0.13 part by mass of 4-methoxyphenol and 0.6 part by mass of BYK-310 were added to 100 parts by mass of the polysiloxane-based compound, diluted with propylene glycol monomethyl acetate so that the concentration of the nonvolatile components became 25%, and coated on a commercially available 50mm square sodium glass substrate using a spin coater (MS-A100, manufactured by MIKASA Co.) under coating conditions of 400rpm for 60 seconds.
Next, after heating (prebaking) at 80℃for 3 minutes, the mixture was subjected to a photolithography machine (mask aligner) (PLA-501 FA, manufactured by Canon Co., ltd.) at 100mJ/cm 2 The test pattern was subjected to a printing treatment (imprinting) under irradiation conditions, and after immersing a part of the test pattern in a 2.38 mass% aqueous solution (developer) of tetramethylammonium hydroxide as the developer for 1 minute, the test pattern was subjected to a heating (post baking) treatment at 150℃for 30 minutes, to prepare a test piece for evaluation.
The film thickness (T1) of the exposed portion of the portion exposed to the developer and the film thickness (T2) of the unexposed portion of the portion are measured by a film thickness measuring device (Alpha-Step IQ surface profiler, manufactured by Ke-epitaxial Co., ltd.), and it is judged that the photo-curability is excellent when T1/T2 is 0.35 or more, and it is judged that the photo-curability is particularly excellent when T1/T2 is 0.55 or more.
The weight average molecular weight (Mw) of the polysiloxane compound of the present invention is preferably 800 to 10000.
If the weight average molecular weight (Mw) is less than 800, the curability of the film-forming composition may be reduced; if the weight average molecular weight (Mw) is more than 10000, the solubility of the film-forming composition may be reduced.
The weight average molecular weight (Mw) of the polysiloxane compound is more preferably 1000 to 5000.
In addition, as the above weight average molecular weight (Mw), it can be measured by the following method: the polysiloxane compound was dissolved to prepare a 0.02 mass% solution, and the solution was filtered through a filter (GL Sciences inc., GL Chromatodisc, water system 25A, pore size 0.2 μm) and then subjected to the following conditions using a semi-trace GPC/SEC analysis system (manufactured by japan spectroscopy) composed of size exclusion chromatography and a refractive index detector.
Column: KF-603 and KF-604 (both made by Showa Denko Co., ltd.) are connected in series
RI detector: RI-4035 (manufactured by Japanese light splitting Co., ltd.)
PDA detector: MD-4015 (manufactured by Japanese light splitting Co., ltd.)
Eluent: THF (tetrahydrofuran)
Flow rate: 1.0ml/min
Injection amount: 100 μl of
< composition for Forming film >
The film-forming composition of the present invention comprises at least the polysiloxane compound, a photo radical polymerization initiator, and an organic solvent.
[ photo radical polymerization initiator ]
Examples of the photo radical polymerization initiator include: acyl phosphine oxides, thioxanthones, aromatic ketones, aromatic onium salts, organic peroxides, thio compounds (thienyl group-containing compounds, etc.), α -aminoalkyl phenones, hexaarylbisimidazoles, ketoxime esters, borates, azinium, metallocenes, active esters, compounds having a carbon halogen bond, and alkylamines.
Among them, in forming a cured film by photolithography, a substance containing a ketoxime ester group is preferable from the viewpoint of improving the photocuring reactivity.
[ organic solvent ]
As the organic solvent, an organic solvent generally used in a coating agent can be used: alcohols, polyols and derivatives thereof, ketone organic solvents, ester organic solvents, and the like.
The alcohols may preferably be lower alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutyl alcohol, and sec-butanol.
Examples of the polyhydric alcohols include ethylene glycol, propylene glycol, 1, 2-butanediol, 1, 3-butanediol, diethylene glycol, dipropylene glycol, and the like.
Examples of the derivative of the polyhydric alcohol include glycol monoethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol monoisobutyl ether, ethylene glycol monophenyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol monoisobutyl ether, propylene glycol monophenyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol monoisopropyl ether, diethylene glycol mono-n-butyl ether, diethylene glycol monoisobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol n-propyl ether, dipropylene glycol isopropyl ether, dipropylene glycol n-butyl ether, dipropylene glycol isobutyl ether, and the like.
Further, examples thereof include glycol monoacylated products such as propylene glycol monomethyl acetate, ethylene glycol monomethyl ether propionate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-propyl ether acetate, ethylene glycol monoisopropyl ether acetate, ethylene glycol mono-n-butyl ether acetate, ethylene glycol monoisobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol mono-n-propyl ether acetate, propylene glycol monoisopropyl ether acetate, propylene glycol mono-n-butyl ether acetate, propylene glycol monoisobutyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono-n-propyl ether acetate, diethylene glycol monoisopropyl ether acetate, diethylene glycol mono-n-butyl ether acetate, diethylene glycol monoisobutyl ether acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl ether acetate, dipropylene glycol mono-n-propyl ether acetate, dipropylene glycol monoisopropyl ether acetate, dipropylene glycol mono-n-butyl ether acetate, dipropylene glycol monoisopropyl ether acetate and the like.
Examples of the ketone organic solvent include acetone, methyl ethyl ketone, methyl n-propyl ketone, methyl isopropyl ketone, methyl n-butyl ketone, methyl isobutyl ketone, and cyclohexanone.
Examples of the ester organic solvent include ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl acetate, isopentyl acetate, methyl propionate, ethyl propionate, methyl lactate, ethyl lactate, and n-propyl lactate.
Such organic solvents may be used alone or in combination of two or more. Further, the polyhydric alcohol derivative and the ester type organic solvent are preferable from the viewpoints of solubility and coating suitability of the polysiloxane compound, and propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol monoisopropyl ether, propylene glycol mono-n-butyl ether, propylene glycol monoisobutyl ether, propylene glycol monomethyl ether acetate, n-propyl acetate and isopropyl acetate are more preferable.
[ polymerizable monomer ]
The film-forming composition of the present invention may contain a polymerizable monomer.
Examples of the photopolymerizable monomers include 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, tetrapropylene glycol di (meth) acrylate, bisphenol a di (meth) acrylate, tris (2-hydroxyethyl) isocyanurate di (meth) acrylate, trimethylolpropane tri (meth) acrylate, glycerol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.
In particular, compounds having a reactive functional group of three or more functions are preferable from the viewpoint of being capable of imparting hardness to the cured film excellently, and for example, trimethylolpropane tri (meth) acrylate, glycerol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and more preferable are tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate.
[ additive ]
The film-forming composition of the present invention may contain the following substances within a range that does not reduce the effect of the present invention: chelate compounds of metals such as aluminum, zirconium, and titanium; a crosslinking agent having crosslinkable functional groups such as carbodiimide groups, isocyanate groups, epoxy groups, thiol groups, and the like; surfactants such as silicon and fluorine; photosensitizers such as aromatic hydrocarbons, amino compounds, nitro compounds, quinones, xanthones, and the like; polymerization inhibitors such as hydroquinone, p-methoxyphenol, hindered amines, hindered phenols, di-t-butylhydroquinone, 4-methoxyphenol, di-t-butylp-methylphenol, and nitrosamine salts; fillers such as inorganic metal oxides and organic microparticles.
[ content of each Material in film-Forming composition ]
The polymerizable monomer is preferably contained in an amount of 10 to 50 parts by mass per 100 parts by mass of the polysiloxane compound.
When the content of the polymerizable monomer is less than 10 parts by mass per 100 parts by mass of the polysiloxane compound, the curability of the cured film and the adhesion to a glass substrate may be insufficient; if the amount of the polysiloxane compound exceeds 50 parts by mass per 100 parts by mass of the polysiloxane compound, the solubility of the uncured coating film in the developer may be insufficient.
The photo radical polymerization initiator is preferably contained in an amount of 0.5 to 40 parts by mass based on 100 parts by mass of the total amount of the polysiloxane compound and the polymerizable monomer.
If the content of the photo radical polymerization initiator is less than 0.5 parts by mass, the photopolymerization property may be lowered, and unreacted components may remain in the exposed portion of the photolithography method; if the content exceeds 40 parts by mass, the storage stability of the film-forming composition may be lowered.
The photo radical polymerization initiator is preferably contained in an amount of 1 to 20 parts by mass based on 100 parts by mass of the total amount of the polysiloxane compound and the polymerizable monomer.
The content of the organic solvent is not particularly limited, and is preferably about 50 to 90% by mass based on the total mass of the film-forming composition, for example.
[ method for producing film-forming composition ]
As a method for producing the film-forming composition of the present invention, the following method can be used: the polysiloxane compound, the photo radical polymerization initiator, and additives used as needed are mixed in a suitable container while being stirred, for example, by a high-speed stirrer.
The method is not limited to this method, and the order of loading the respective materials may be arbitrary. In addition, in the case of a solid material, if it is soluble in an organic solvent, it may be dissolved in the organic solvent in advance before being put in; if the dispersion can be carried out directly or by using a dispersant or the like, the dispersion may be carried out in advance in the organic solvent before the dispersion is carried out.
[ physical Properties of film-Forming composition ]
The film-forming composition of the present invention is excellent in adhesion.
Regarding the above adhesion, it can be judged by the following test.
The film-forming composition was diluted with propylene glycol monomethyl acetate so that the concentration of the nonvolatile component became 25% by mass, and a polysiloxane compound (i.e., film-forming composition) was applied to a commercially available 50mm square sodium glass substrate under application conditions of 400rpm and 60 seconds using a spin coater (MS-A100, manufactured by MIKASA Co.).
Subsequently, the test piece for evaluation was prepared by heating (prebaking) at 80℃for 3 minutes.
The degree of trace remaining when the surface of the evaluation test piece to which the film-forming composition was applied was touched with a finger was visually confirmed, and if no trace was found by the finger, it was judged that the adhesion was excellent.
The composition for forming a film of the present invention is excellent in developability.
The developability can be determined by the following test.
The test piece for evaluation used in the adhesion test of the film-forming composition was exposed to a 2.38 mass% aqueous solution of tetramethylammonium hydroxide (developing solution), and the dissolution state was visually observed, and when complete dissolution was confirmed, it was judged that the developability was excellent.
The composition for forming a film of the present invention is excellent in photocurability.
The above photocurability can be determined by the following test.
100 parts by mass of the film-forming composition was diluted with propylene glycol monomethyl ether acetate so that the concentration of the nonvolatile component became 25%, and applied to a commercially available 50mm square sodium glass substrate using a spin coater (MS-A100, manufactured by MIKASA) at 400rpm for 60 seconds.
Next, after heating (prebaking) at 80℃for 3 minutes, a lithography machine (PLA-501 FA, canon strain) was usedManufactured by Seisakusho Co., ltd.) at 100mJ/cm 2 The test pattern was subjected to a printing treatment under irradiation conditions, and after immersing a part of the test pattern in a 2.38 mass% aqueous solution (developer) of tetramethylammonium hydroxide as the developer for 1 minute, the test pattern was subjected to a heating (post-baking) treatment at 150℃for 30 minutes, to prepare a test piece for evaluation.
The film thickness (T1) of the exposed portion of the portion exposed to the developer and the film thickness (T2) of the unexposed portion of the portion are measured by a film thickness measuring device (Alpha-Step IQ surface profiler, manufactured by Ke-epitaxial Co., ltd.), and it is judged that the photo-curability is excellent when T1/T2 is 0.35 or more, and it is judged that the photo-curability is particularly excellent when T1/T2 is 0.55 or more.
The film-forming composition of the present invention is preferably excellent in corrosion evaluation.
The above erosion evaluation can be judged by the following test.
When the test piece for evaluation used in the test of the photocurability of the film-forming composition was exposed to a developer, the dissolution rate (nm/s) was evaluated by dividing the width of line pattern portion of the exposed portion (narrowing width) by the development time.
The above dissolution rate is preferably less than 1200nm/s, more preferably less than 600nm/s.
< method for Forming cured coating >
The method for forming a coating film according to the present invention comprises: a coating step of coating the film-forming composition of the present invention on a substrate; an exposure step of irradiating an exposure portion with an active energy ray to form a cured film; and a developing step of dissolving and removing the coating liquid of the unexposed portion with a developing liquid.
The coating method in the coating step, the active energy beam irradiated to the exposure portion in the exposure step, the irradiation method thereof, and the developer for removing the coating liquid from the exposure portion can be appropriately selected and used as conventionally used in photolithography.
For example, it is preferable that the film-forming composition is diluted so that the concentration of the nonvolatile component becomes 25%, and is applied by a spin coater at 80℃for 3 minutesAfter the heating (prebaking) treatment, a photolithography machine was used to heat the substrate at 100mJ/cm 2 The test pattern was subjected to a printing treatment under irradiation conditions, immersed in a developer for 1 minute, and then subjected to a heating (post baking) treatment at 150 ℃ for 30 minutes or the like, whereby a cured film was obtained.
As the conditions for the preliminary baking, the treatment is carried out at 80 to 100℃for 1 to 3 minutes.
The irradiation conditions are preferably 20 to 120mJ/cm 2 。
As the post-baking conditions, it is preferable to perform the treatment at 120 to 180℃for 30 to 60 minutes
The substrate may be a glass substrate or a plastic substrate, which has been conventionally known as a touch panel, and may be a substrate having a transparent electrode formed on a surface thereof.
In the case where the transparent electrode is provided on the surface, it is preferable to form a cured film of the film-forming composition of the present invention on the surface on which the transparent electrode is formed.
A laminate is also one aspect of the present invention, and is characterized in that the substrate has a cured film of the film-forming composition of the present invention.
In addition, a touch panel is also an aspect of the present invention, and is characterized in that the touch panel is configured using the laminate of the present invention.
As a material constituting the touch panel, a conventionally known material may be appropriately used in addition to the laminate of the present invention.
Examples
The present invention will be described in further detail by referring to examples, but the present invention is not limited to these examples. In addition, "%" means "% by mass" and "parts" means "parts by mass" unless otherwise specified.
As the silane compounds (a) to (C) used in the synthesis of the polysiloxane compounds, the following compounds were prepared.
< silane-based Compound (A) >)
Tetraethoxysilane
< silane-based Compound (B) >)
Phenyl trimethoxysilane
Methyltriethoxysilane
Dimethyl dimethoxy silane
< silane-based Compound (C) >)
3- (methacryloyloxy) propyl trimethoxysilane
Examples 1 to 3 and comparative examples 1 to 8
(Synthesis of polysiloxane Compound)
The silane compound (a), the silane compound (B) and the silane compound (C) were added to a reaction vessel equipped with a stirring device, a reflux condenser, a thermometer and a dropping funnel in such a manner that the total mass of the silane compounds (a), B) and C was 100g, according to the mixing ratio shown in table 1. Then, dissolved in 400g of isopropanol and a homogeneous solution was formed.
Further, water and nitric acid were added to the total molecular weight of the added silane compound (a), silane compound (B) and silane compound (C) while stirring so that the molecular weight of water became 4 times and the molecular weight of nitric acid became 0.1 times, respectively, and the mixture was refluxed for 3 hours, and then the obtained reaction solution was cooled to room temperature.
Then, 20.00g of propylene glycol monomethyl ether acetate was added to the reaction solution, and methanol, water and nitric acid as reaction by-products were distilled off under reduced pressure to obtain a hydrolysis condensate solution.
Then, propylene glycol monomethyl ether acetate was added to the hydrolysis condensate solution to obtain a hydrolysis condensate solution (polysiloxane compound solution) having a concentration of 45 mass% of the nonvolatile component of the polysiloxane compound.
The weight average molecular weight (Mw) of the polysiloxane compound is in the range of 800 to 10000 when measured under the conditions described in the present specification.
The numerical values shown in the line of the names of the compounds in table 1 represent the number of moles, and the numerical values shown in the line of [ MC/(ma+mb) ] represent the composition ratio calculated by the above formula (1).
< evaluation of Silicone Compound >
(adhesion)
[ production of test pieces for evaluation ] the synthesized polysiloxane compounds were each diluted with propylene glycol monomethyl acetate so that the concentration of the nonvolatile components became 25% by mass, and the polysiloxane compounds were applied to a commercially available 50mm square sodium glass substrate under application conditions of 400rpm and 60 seconds using a spin coater (MS-A100, manufactured by MIKASA CO., LTD).
Subsequently, the mixture was heated (prebaked) at 80℃for 3 minutes to prepare a test piece for evaluation.
Evaluation results the degree of trace residue upon finger touch was visually confirmed on the surface coated with the silicone compound of the test piece for evaluation, and the adhesion of the silicone compound was evaluated according to the following evaluation criteria. The results are shown in table 1.
And (2) the following steps: the trace of the finger is completely free of residues;
delta: a little finger mark remains;
x: the finger trace is clear.
(developability)
The test piece for evaluation prepared at the time of evaluating the adhesion was exposed to a 2.38 mass% aqueous solution (developing solution) of tetramethylammonium hydroxide, and the dissolution state was visually observed, and the developability of the polysiloxane compound was evaluated according to the following evaluation criteria. The results are shown in table 1.
And (2) the following steps: completely dissolving;
delta: substantially dissolved but producing a residue;
x: does not dissolve.
(photo-curing Property)
[ production of test piece for evaluation ] 2.5 parts by mass of Irgacure OXE02, 0.13 part by mass of 4-methoxyphenol, and 0.6 part by mass of BYK-310 were added to 100 parts by mass of each of the synthesized polysiloxane-based compounds, and the mixture was diluted with propylene glycol monomethyl acetate so that the concentration of the nonvolatile components became 25%, and coated on a commercially available 50mm square sodium glass substrate using a spin coater (MS-A100, manufactured by MIKASA Co.) under coating conditions of 400rpm for 60 seconds.
Next, after heating (prebaking) at 80℃for 3 minutes, the mixture was subjected to a photolithography machine (PLA-501 FA, manufactured by Canon Co., ltd.) at 100mJ/cm 2 The test pattern was subjected to a printing treatment under irradiation conditions, and after immersing a part of the test pattern in a 2.38 mass% aqueous solution (developer) of tetramethylammonium hydroxide as the developer for 1 minute, the test pattern was subjected to a heating (post-baking) treatment at 150℃for 30 minutes, to prepare a test piece for evaluation.
Evaluation results the photo-curability of the polysiloxane compound was evaluated on the basis of the following evaluation criteria by measuring the film thickness (T1) of the exposed portion of the portion exposed to the developer and the film thickness (T2) of the unexposed portion of the portion not exposed by using a film thickness measuring device (Alpha-Step IQ surface profiler, manufactured by Ke-epitaxial Co., ltd.). The results are shown in table 1.
And (2) the following steps: T1/T2 is more than 0.55;
delta: T1/T2 is 0.35 or more and less than 0.55;
x: T1/T2 is less than 0.35.
TABLE 1
< preparation of composition for Forming coating >
As materials for producing the film-forming composition, the following materials were prepared.
< polymerizable monomer >
Tris (2-hydroxyethyl) isocyanurate triacrylate (THITA, manufactured by Tokyo chemical industry Co., ltd.)
Dipentaerythritol hexaacrylate (DPHA, manufactured by Tokyo chemical industry Co., ltd.)
< polymerization initiator >
O-acetyl-1- [6- (2-methylbenzoyl) -9-ethyl-9H-carbazol-3-yl ] ethanone oxime (Irgacure OXE02, manufactured by BASF Japanese Co., ltd.)
< other materials >
Karenz MT PE-1 (thiol-based crosslinking agent, manufactured by Zhaoyao electric Co., ltd.)
4-methoxyphenol (polymerization inhibitor, 4-MeOPh, manufactured by Tokyo chemical industry Co., ltd.)
BYK-310 (Silicone surfactant, manufactured by Bike chemical Co., ltd.)
Example 4
In a container equipped with a high-speed stirring device, 100 parts by mass of the polysiloxane compound solution (non-volatile component concentration: 45%) prepared in example 1, 15 parts by mass of THITA, 5 parts by mass of DPHA, 5 parts by mass of Karenz MT PE-1, 2.5 parts by mass of Irgacure OXE02, 0.13 part by mass of 4-MeOPh, 0.6 part by mass of BYK-310 and 135 parts by mass of Propylene Glycol Monomethyl Ether Acetate (PGMEA) were added and stirred to prepare a film-forming composition of example 4.
Examples 5 to 6 and comparative examples 9 to 16
A film-forming composition was produced in the same manner as in example 4, except that the types of the polysiloxane compound solutions were changed as shown in table 2.
In addition, although not shown in table 2, 135 parts by mass of Propylene Glycol Monomethyl Ether Acetate (PGMEA) was used in the same manner as in example 1.
(adhesion)
[ production of test pieces for evaluation ] each of the produced film-forming compositions was diluted with propylene glycol monomethyl ether acetate so that the concentration of nonvolatile components became 25% by mass, and each film-forming composition was applied to a commercially available 50mm square sodium glass substrate under application conditions of 400rpm and 60 seconds using a spin coater (MS-A100, manufactured by MIKASA Co.).
Subsequently, the mixture was heated (prebaked) at 80℃for 3 minutes to prepare a test piece for evaluation.
Evaluation results the degree of trace residue when touched with a finger on the surface of the prepared evaluation test piece coated with the film-forming composition was visually confirmed, and the adhesiveness of the film-forming composition was evaluated according to the following evaluation criteria. The results are shown in table 2.
And (2) the following steps: the trace of the finger is completely free of residues;
delta: a little finger mark remains;
x: the finger trace is clear.
(developability)
The test piece for evaluation prepared at the time of evaluating the adhesion was exposed to a 2.38 mass% aqueous solution (developing solution) of tetramethylammonium hydroxide, and the dissolution state was visually observed, and the developability of the polysiloxane compound was evaluated according to the following evaluation criteria. The results are shown in table 2.
And (2) the following steps: completely dissolving;
delta: substantially dissolved but producing a residue;
x: does not dissolve.
(photo-curing Property)
[ production of test pieces for evaluation ] each of the produced film-forming compositions was diluted with propylene glycol monomethyl ether acetate so that the concentration of nonvolatile components became 25% by mass, and each film-forming composition was applied to a commercially available 50mm square sodium glass substrate under application conditions of 400rpm and 60 seconds using a spin coater (MS-A100, manufactured by MIKASA Co.).
Next, after heating (prebaking) at 80℃for 3 minutes, the mixture was subjected to a photolithography machine (PLA-501 FA, manufactured by Canon Co., ltd.) at 100mJ/cm 2 The test pattern was subjected to a printing treatment under irradiation conditions, and after immersing a part of the test pattern in a 2.38 mass% aqueous solution (developer) of tetramethylammonium hydroxide as the developer for 1 minute, the test pattern was subjected to a heating (post-baking) treatment at 150℃for 30 minutes, to prepare a test piece for evaluation.
Evaluation results the film thickness (T1) of the exposed portion of the portion exposed to the developer and the film thickness (T2) of the unexposed portion of the portion were measured by using a film thickness measuring device (Alpha-Step IQ surface profiler, manufactured by kei epitaxy corporation, KLM-Tencor), and the photocurability of the film-forming composition was evaluated according to the following evaluation criteria. The results are shown in table 2.
And (2) the following steps: T1/T2 is more than 0.55;
delta: T1/T2 is 0.35 or more and less than 0.55;
x: T1/T2 is less than 0.35.
(erosion)
When the test piece for evaluation produced in the above-described developability evaluation was exposed to a developing solution, the value obtained by dividing the thinned width (narrowing width) of the line pattern portion of the exposed portion by the development time was used as the dissolution rate (nm/s), and the evaluation was performed as follows. The results are shown in table 2.
And (2) the following steps: the dissolution speed is less than 600nm/s;
delta: the dissolution rate is 600nm/s or more and less than 1200nm/s;
x: the dissolution rate is more than 1200 nm/s.
TABLE 2
It was confirmed that the polysiloxane compounds of examples 1 to 3 were excellent in adhesion and developability and also excellent in photocurability. It was also confirmed that the film-forming compositions of examples 4 to 6 using the polysiloxane compounds of examples 1 to 3 were excellent in the evaluation of adhesion, developability, photocurability and corrosion.
On the other hand, the polysiloxane compounds of comparative examples 1 to 6 and 8 having a composition ratio of 0.1 or more calculated from the above formula (1) were insufficient in adhesion. The film-forming compositions of comparative examples 9 to 14 and 16 using the polysiloxane compounds of comparative examples 1 to 6 and 8 were also insufficient in adhesion.
The polysiloxane compound of comparative example 7 having a composition ratio of 0 calculated from the above formula (1) was insufficient in photocurability. The composition for forming a film of comparative example 15 using the polysiloxane compound of comparative example 7 was also insufficient in photocurability and corrosion.
The following technical scheme is disclosed in the specification.
The scheme (1) of the disclosure is a polysiloxane compound, which at least comprises a structural unit (A), a structural unit (B) and a structural unit (C); the structural unit (a) is derived from a silane-based compound (a) selected from at least one of the group consisting of tetraalkoxysilane and bis (trialkoxysilyl) alkane; the structural unit (B) is derived from a silane compound (B) selected from at least one of the group consisting of alkyl trialkoxysilane, dialkyl dialkoxysilane, cycloalkyl trialkoxysilane, vinyl trialkoxysilane and phenyl trialkoxysilane; the structural unit (C) is derived from a silane compound (C) having a radically polymerizable unsaturated double bond. The composition ratio of the polysiloxane compound calculated by the following formula (1) is more than 0 and less than 0.1,
In the formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).
The present disclosure (2) is the polysiloxane-based compound of the present disclosure (1), wherein the silane-based compound (a) is tetraethoxysilane.
The polysiloxane-based compound according to the embodiment (3) of the present disclosure is the polysiloxane-based compound according to the embodiment (1) or (2), wherein the silane-based compound (B) is phenyl trimethoxysilane and/or methyltriethoxysilane.
The present disclosure item (4) is the polysiloxane-based compound according to any one of the present disclosure items (1) to (3), wherein the silane-based compound (C) is 3- (methacryloyloxy) propyl trimethoxysilane.
The present disclosure (5) is the polysiloxane-based compound according to any one of the present disclosure (1) to (4), wherein the composition ratio calculated from the formula (1) is 0.03 or more and 0.08 or less.
The present disclosure (6) is a film-forming composition comprising at least the polysiloxane-based compound according to any one of the present disclosure (1) to (5), a photo radical polymerization initiator, and an organic solvent.
The present disclosure (7) is the film-forming composition according to the present disclosure (6), wherein the photo-radical polymerization initiator contains a ketoxime ester group.
The present disclosure (8) is a laminate obtained by applying the coating film-forming composition according to the present disclosure (6) or (7).
The present disclosure (9) is a touch panel formed by using the laminate of the present disclosure (8).
The present disclosure provides (10) a method for forming a cured coating, comprising: a coating step of coating the film-forming composition according to the embodiment (6) or (7) of the present disclosure; an exposure step of irradiating an exposure portion with an active energy ray to form a cured film; and a developing step of dissolving and removing the coating liquid in the unexposed portion with a developing liquid.
Industrial applicability
The polysiloxane compound of the present invention can provide a cured film excellent in adhesion, and is excellent in developability and photocurability, and therefore can be suitably used as a film to be applied to a light-transmitting substrate such as a touch panel.
Claims (10)
1. A polysiloxane compound comprising at least a structural unit (A), a structural unit (B) and a structural unit (C),
the structural unit (A) is derived from a silane compound (A) selected from at least one of the group consisting of tetraalkoxysilane and bis (trialkoxysilyl) alkane,
The structural unit (B) is derived from a silane compound (B) selected from at least one of the group consisting of alkyl trialkoxysilane, dialkyl dialkoxysilane, cycloalkyl trialkoxysilane, vinyl trialkoxysilane and phenyl trialkoxysilane,
the structural unit (C) is derived from a silane compound (C) having a radical polymerizable unsaturated double bond;
the composition ratio of the polysiloxane compound calculated by the following formula (1) is more than 0 and less than 0.1,
in the formula (1), MA represents the number of moles of the structural unit (A), MB represents the number of moles of the structural unit (B), and MC represents the number of moles of the structural unit (C).
2. The polysiloxane-based compound according to claim 1, wherein the silane-based compound (a) is tetraethoxysilane.
3. Polysiloxane compound according to claim 1 or 2, wherein the silane compound (B) is phenyltrimethoxysilane and/or methyltriethoxysilane.
4. The polysiloxane-based compound according to claim 1 or 2, wherein the silane-based compound (C) is 3- (methacryloyloxy) propyl trimethoxysilane.
5. The polysiloxane compound according to claim 1 or 2, wherein the composition ratio calculated from the formula (1) is 0.03 or more and 0.08 or less.
6. A composition for forming a film, comprising at least the polysiloxane compound according to claim 1 or 2, a photo radical polymerization initiator, and an organic solvent.
7. The film-forming composition according to claim 6, wherein the photo-radical polymerization initiator comprises a ketoxime ester group.
8. A laminate obtained by applying the film-forming composition according to claim 6.
9. A touch panel comprising the laminate according to claim 8.
10. A method for forming a cured coating film, comprising:
a coating step of coating the film-forming composition according to claim 6;
an exposure step of irradiating an exposure portion with an active energy ray to form a cured film; and
and a developing step of dissolving and removing the coating liquid in the unexposed portion with a developing liquid.
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JP2022080415A JP2023168981A (en) | 2022-05-16 | 2022-05-16 | Polysiloxane-based compound, film-forming composition, laminate, touch panel, and method for forming cured film |
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