WO2023054561A1 - 硬化性樹脂組成物、コーティング層、及び、フィルム - Google Patents
硬化性樹脂組成物、コーティング層、及び、フィルム Download PDFInfo
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- WO2023054561A1 WO2023054561A1 PCT/JP2022/036375 JP2022036375W WO2023054561A1 WO 2023054561 A1 WO2023054561 A1 WO 2023054561A1 JP 2022036375 W JP2022036375 W JP 2022036375W WO 2023054561 A1 WO2023054561 A1 WO 2023054561A1
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- WO
- WIPO (PCT)
- Prior art keywords
- curable resin
- resin composition
- weight
- cationically polymerizable
- examples
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 75
- 239000011247 coating layer Substances 0.000 title claims abstract description 12
- 239000010408 film Substances 0.000 title 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 15
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 239000003505 polymerization initiator Substances 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 7
- 239000013008 thixotropic agent Substances 0.000 claims description 6
- -1 silane compound Chemical class 0.000 description 60
- 239000000975 dye Substances 0.000 description 16
- 125000002091 cationic group Chemical group 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 239000004065 semiconductor Substances 0.000 description 8
- 238000010538 cationic polymerization reaction Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical class CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- PFHLXMMCWCWAMA-UHFFFAOYSA-N [4-(4-diphenylsulfoniophenyl)sulfanylphenyl]-diphenylsulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC(C=C1)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 PFHLXMMCWCWAMA-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010943 off-gassing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FCKXGFANXSHGAW-DTXPUJKBSA-N (2s)-n,n'-bis[(2s)-1-(2-chloro-4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]-2-hydroxybutanediamide Chemical compound C([C@H](NC(=O)C[C@H](O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NC=1C(=CC(=CC=1)[N+]([O-])=O)Cl)C(=O)NC=1C(=CC(=CC=1)[N+]([O-])=O)Cl)C1=CC=CC=C1 FCKXGFANXSHGAW-DTXPUJKBSA-N 0.000 description 2
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- UFERIGCCDYCZLN-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-1h-indene Chemical compound C1C=CCC2CC=CC21 UFERIGCCDYCZLN-UHFFFAOYSA-N 0.000 description 2
- RRXFVFZYPPCDAW-UHFFFAOYSA-N 4-(7-oxabicyclo[4.1.0]heptan-4-ylmethoxymethyl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1COCC1CC2OC2CC1 RRXFVFZYPPCDAW-UHFFFAOYSA-N 0.000 description 2
- 102100033806 Alpha-protein kinase 3 Human genes 0.000 description 2
- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- 125000003566 oxetanyl group Chemical group 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical class CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- HIYIGPVBMDKPCR-UHFFFAOYSA-N 1,1-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1(COC=C)CCCCC1 HIYIGPVBMDKPCR-UHFFFAOYSA-N 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical compound C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 description 1
- BMSRLPMIICHPCT-UHFFFAOYSA-N 1,3-bis(oxiran-2-yl)-1,3-dihydro-2-benzofuran Chemical compound C1OC1C1C2=CC=CC=C2C(C2OC2)O1 BMSRLPMIICHPCT-UHFFFAOYSA-N 0.000 description 1
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
- RQJCIXUNHZZFMB-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxypropoxy)propane Chemical compound C=COCC(C)OCC(C)OC=C RQJCIXUNHZZFMB-UHFFFAOYSA-N 0.000 description 1
- FOWNZLLMQHBVQT-UHFFFAOYSA-N 1-ethenoxy-2-[2-(2-ethenoxypropoxy)propoxy]propane Chemical compound C=COCC(C)OCC(C)OCC(C)OC=C FOWNZLLMQHBVQT-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- ITLDHFORLZTRJI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1N1N=C2C=CC=CC2=N1 ITLDHFORLZTRJI-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- RQZUWSJHFBOFPI-UHFFFAOYSA-N 2-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COCC1CO1 RQZUWSJHFBOFPI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 1
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 1
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002841 Lewis acid Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- MOOIXEMFUKBQLJ-UHFFFAOYSA-N [1-(ethenoxymethyl)cyclohexyl]methanol Chemical compound C=COCC1(CO)CCCCC1 MOOIXEMFUKBQLJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000006059 cover glass Substances 0.000 description 1
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 1
- JFHGLVIOIANSIN-UHFFFAOYSA-N dimethyl butanedioate;1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound COC(=O)CCC(=O)OC.CC1(C)CC(O)CC(C)(C)N1CCO JFHGLVIOIANSIN-UHFFFAOYSA-N 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Definitions
- the present invention relates to a curable resin composition.
- the present invention also relates to coating layers and films formed using the curable resin composition.
- Optical semiconductor devices such as LEDs consume low power and have a long life, so they are widely used for backlights of liquid crystal display devices, lighting fixtures, and the like.
- An optical semiconductor element deteriorates when it comes into contact with moisture or gas in the atmosphere, and the light extraction efficiency decreases.
- a method for protecting and sealing optical semiconductor elements without using a cover glass or the like it has been studied to form a coating layer on the surface of the optical semiconductor element using a hard coating agent (for example, Patent Document 1 etc).
- An object of the present invention is to provide a curable resin composition that is excellent in colorability and hardness of the cured product. Another object of the present invention is to provide a coating layer and a film formed using the curable resin composition.
- the present disclosure 1 is a curable resin composition containing a curable resin, a photopolymerization initiator and a dye, wherein the curable resin is polysilsesquioxane having a cationically polymerizable group and the cationically polymerizable A curable resin composition containing a cationic polymerizable compound other than polysilsesquioxane having a group.
- the present disclosure 2 is the curable resin composition of the present disclosure 1, which has a viscosity of 500 mPa ⁇ s or more and 50,000 mPa ⁇ s or less.
- the present disclosure 3 is the curable resin composition of the present disclosure 1 or 2, wherein the photopolymerization initiator includes a photocationic polymerization initiator.
- This disclosure 4 is the curable resin composition of this disclosure 1, 2 or 3, further comprising an ultraviolet absorber.
- Disclosure 5 is the curable resin composition of Disclosure 1, 2, 3 or 4 further comprising a leveling agent.
- the present disclosure 6 is the curable resin composition of the present disclosure 1, 2, 3, 4 or 5 further comprising a thixotropic agent.
- the present disclosure 7 is a coating layer formed using the curable resin composition of the present disclosure 1, 2, 3, 4, 5 or 6.
- the present disclosure 8 is a film formed using the curable resin composition of the present disclosure 1, 2, 3, 4, 5 or 6. The present invention will be described in detail below.
- the present inventors added a dye instead of the pigment to the curable resin composition, and further improved the hardness of the cured product.
- the use of a polysilsesquioxane having a cationically polymerizable group in combination with another cationically polymerizable compound was investigated.
- the present inventors have found that it is possible to obtain a curable resin composition having excellent coloring properties and hardness of the cured product, and have completed the present invention.
- the curable resin composition of the present invention is also excellent in low outgassing properties by using polysilsesquioxane having a cationic polymerizable group.
- the curable resin composition of the present invention contains a curable resin.
- the curable resin is a polysilsesquioxane having a cationically polymerizable group (hereinafter also referred to as "cationically polymerizable polysilsesquioxane") and a polysilsesquioxane other than the polysilsesquioxane having the cationically polymerizable group.
- cationically polymerizable polysilsesquioxane a polysilsesquioxane other than the polysilsesquioxane having the cationically polymerizable group.
- polysilsesquioxane is a compound having a repeating structure of RSiO 1.5 (R is a hydrogen atom or an organic group) unit, and a silicon atom is added with an alkoxy group or the like. It is a compound having a network structure derived from a silane compound in which three decomposable groups are bonded.
- the cationically polymerizable polysilsesquioxane and the other cationically polymerizable compound have a cationically polymerizable group.
- Examples of the cationic polymerizable group include an epoxy group, an oxetanyl group, and a vinyl ether group. Among them, an epoxy group and an oxetanyl group are preferable.
- the cationically polymerizable group of the cationically polymerizable polysilsesquioxane and the cationically polymerizable group of the other cationically polymerizable compound may be the same or different.
- the cationically polymerizable polysilsesquioxane may have any one of a random structure, a ladder structure, and a cage structure, or may be a mixture of structures having these structures.
- a preferable lower limit of the content of the cationic polymerizable polysilsesquioxane in 100 parts by weight of the curable resin is 20 parts by weight, and a preferable upper limit is 80 parts by weight.
- the content of the cationically polymerizable polysilsesquioxane is 20 parts by weight or more, the obtained curable resin composition becomes excellent in hardness of the cured product.
- the content of the cationically polymerizable polysilsesquioxane is 80 parts by weight or less, the resulting curable resin composition has excellent coating properties.
- a more preferable lower limit to the content of the cationic polymerizable polysilsesquioxane is 40 parts by weight, and a more preferable upper limit is 70 parts by weight.
- Examples of the other cationic polymerizable compounds include 3,4-epoxycyclohexylmethyl(3,4-epoxy)cyclohexane carboxylate, 4,4′-bis(1,2-epoxycyclohexane), tetrahydroindene diepoxide, Bis(3,4-epoxycyclohexylmethyl)ether, bis(3,4-epoxycyclohexan-1-ylmethyl)adipate, 1,2-epoxy-4- of 2,2-bis(hydroxymethyl)-1-butanol (2-oxiranyl) cyclohexane adduct, [(3,4-epoxycyclohexane)-1-yl]methyl methacrylate, fluorene type epoxy compound, 1,7-octadiene diepoxide, neopentyl glycol diglycidyl ether, ethylene glycol Diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidy
- alicyclic epoxy compounds are preferred, and 3,4-epoxycyclohexylmethyl (3,4-epoxy)cyclohexanecarboxy 4,4′-bis(1,2-epoxycyclohexane), tetrahydroindene diepoxide, bis(3,4-epoxycyclohexylmethyl)ether are more preferred.
- a preferable lower limit of the content of the other cationic polymerizable compound in 100 parts by weight of the curable resin is 10 parts by weight, and a preferable upper limit thereof is 60 parts by weight.
- the content of the other cationically polymerizable compound is 10 parts by weight or more, the resulting curable resin composition has excellent curability.
- the content of the other cationically polymerizable compound is 60 parts by weight or less, the obtained curable resin composition becomes excellent in hardness of the cured product.
- a more preferable lower limit of the content of the other cationic polymerizable compound is 15 parts by weight, and a more preferable upper limit thereof is 50 parts by weight.
- the curable resin composition of the present invention contains a photopolymerization initiator.
- the photopolymerization initiator preferably contains a photocationic polymerization initiator.
- the photocationic polymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by light irradiation, and may be an ionic photoacid-generating type or a nonionic photoacid-generating type. may
- anion portion of the ionic photoacid-generating photocationic polymerization initiator examples include BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , (BX 4 ) ⁇ (wherein X is at least two or more fluorine or a phenyl group substituted with a trifluoromethyl group). Further, as the anion portion, PF m (C n F 2n+1 ) 6-m ⁇ (wherein m is an integer of 0 or more and 5 or less, and n is an integer of 1 or more and 6 or less), etc. mentioned.
- Examples of the ionic photoacid-generating photocationic polymerization initiator include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, aromatic ammonium salts, (2,4-cyclo pentadien-1-yl)((1-methylethyl)benzene)-Fe salts and the like.
- aromatic sulfonium salts include bis(4-(diphenylsulfonio)phenyl)sulfide bishexafluorophosphate, bis(4-(diphenylsulfonio)phenyl)sulfide bishexafluoroantimonate, bis(4-( diphenylsulfonio)phenyl)sulfide bistetrafluoroborate, bis(4-(diphenylsulfonio)phenyl)sulfidetetrakis(pentafluorophenyl)borate, diphenyl-4-(phenylthio)phenylsulfonium hexafluorophosphate, diphenyl-4-( phenylthio)phenylsulfonium hexafluoroantimonate, diphenyl-4-(phenylthio)phenylsulfonium tetrafluoroborate, diphenyl
- triarylsulfonium tetrakis(pentafluorophenyl)borate such as triphenylsulfonium tetrakis(pentafluorophenyl)borate is preferable.
- aromatic iodonium salts include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis(pentafluorophenyl)borate, bis(dodecylphenyl)iodonium hexafluorophosphate, bis (dodecylphenyl)iodonium hexafluoroantimonate, bis(dodecylphenyl)iodonium tetrafluoroborate, bis(dodecylphenyl)iodonium tetrakis(pentafluorophenyl)borate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexa fluorophosphate, 4-methylphenyl-4-(1-methylethyl)
- aromatic diazonium salts examples include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, and phenyldiazonium tetrakis(pentafluorophenyl)borate.
- aromatic ammonium salts examples include 1-benzyl-2-cyanopyridinium hexafluorophosphate, 1-benzyl-2-cyanopyridinium hexafluoroantimonate, 1-benzyl-2-cyanopyridinium tetrafluoroborate, 1-benzyl -2-cyanopyridinium tetrakis(pentafluorophenyl)borate, 1-(naphthylmethyl)-2-cyanopyridinium hexafluorophosphate, 1-(naphthylmethyl)-2-cyanopyridinium hexafluoroantimonate, 1-(naphthylmethyl) -2-cyanopyridinium tetrafluoroborate, 1-(naphthylmethyl)-2-cyanopyridinium tetrakis(pentafluorophenyl)borate and the like.
- Examples of the (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe salt include (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene )-Fe(II) hexafluorophosphate, (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe(II) hexafluoroantimonate, (2,4-cyclopentadiene-1 -yl)((1-methylethyl)benzene)-Fe(II) tetrafluoroborate, (2,4-cyclopentadien-1-yl)((1-methylethyl)benzene)-Fe(II) tetrakis(penta fluorophenyl)borate and the like.
- nonionic photoacid-generating photocationic polymerization initiator examples include nitrobenzyl esters, sulfonic acid derivatives, phosphoric acid esters, phenolsulfonic acid esters, diazonaphthoquinone, and N-hydroxyimide sulfonates.
- Examples of commercially available photocationic polymerization initiators include, for example, a photocationic polymerization initiator manufactured by Midori Chemical Co., Ltd., a photocationic polymerization initiator manufactured by Union Carbide, a photocationic polymerization initiator manufactured by ADEKA, Photocationic polymerization initiators manufactured by 3M, photocationic polymerization initiators manufactured by BASF, photocationic polymerization initiators manufactured by Solvay, and photocationic polymerization initiators manufactured by San-Apro. Examples of the photocationic polymerization initiator manufactured by Midori Kagaku Co., Ltd. include DTS-200 and the like. Examples of photo cationic polymerization initiators manufactured by Union Carbide include UVI6990 and UVI6974.
- Examples of photo cationic polymerization initiators manufactured by ADEKA include SP-150 and SP-170. Examples of photo cationic polymerization initiators manufactured by 3M include FC-508 and FC-512. Examples of photo cationic polymerization initiators manufactured by BASF include IRGACURE261 and IRGACURE290. Examples of photo cationic polymerization initiators manufactured by Solvay include PI2074. Examples of photo cationic polymerization initiators manufactured by San-Apro include CPI-100P, CPI-200K, CPI-210S and the like.
- a preferred lower limit to the content of the photopolymerization initiator is 1 part by weight, and a preferred upper limit is 20 parts by weight with respect to 100 parts by weight of the curable resin.
- a preferred lower limit for the content of the photopolymerization initiator is 3 parts by weight, and a more preferable upper limit is 16 parts by weight.
- the curable resin composition of the invention contains a dye. By containing the dye, the curable resin composition of the present invention becomes excellent in colorability.
- Cationic dyes and anionic dyes can be used as the above dyes, and examples thereof include azine dyes, oxazine dyes, allylmethane dyes, and azo dyes.
- the azine-based dyes are preferable, and the nigrosine-based dyes are more preferable because of their high blackness, high heat resistance, high solubility, and high molecular weight.
- the preferred lower limit is 0.1 parts by weight and the preferred upper limit is 5 parts by weight with respect to 100 parts by weight of the curable resin.
- the content of the dye is 0.1 parts by weight or more, the resulting curable resin composition is more excellent in colorability.
- the content of the dye is 5 parts by weight or less, the obtained curable resin composition has excellent deep-part curability.
- a more preferable lower limit of the dye content is 0.5 parts by weight, and a more preferable upper limit is 2 parts by weight.
- the curable resin composition of the present invention preferably further contains an ultraviolet absorber.
- Examples of the ultraviolet absorber include 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, bisanilide 2-ethoxy-2'-ethyloxalate, and dimethyl-1-(2-hydroxyethyl) succinate.
- -4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-4'-n- octoxyphenyl)benzotriazole, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, phenyl salicylate, pt-butylphenyl salicylate, 2-ethylhexyl 2-cyano-3,3- diphenyl acrylate, 2-ethoxy-2'-ethyl oxalic acid bisanilide, dimethyl succinate-1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpipe
- the content of the ultraviolet absorber has a preferable lower limit of 0.001 parts by weight and a preferable upper limit of 5 parts by weight with respect to 100 parts by weight of the curable resin. When the content of the ultraviolet absorber is within this range, the resulting curable resin composition is more excellent in light resistance.
- a more preferable lower limit to the content of the ultraviolet absorber is 0.1 part by weight, and a more preferable upper limit is 1 part by weight.
- the curable resin composition of the present invention preferably further contains a leveling agent.
- leveling agent examples include silicone leveling agents, fluorine leveling agents, and acrylic leveling agents.
- the content of the leveling agent has a preferable lower limit of 0.01 parts by weight and a preferable upper limit of 10 parts by weight with respect to 100 parts by weight of the curable resin.
- the content of the leveling agent is within this range, the resulting curable resin composition is more excellent in coatability and flatness of the coating film.
- a more preferable lower limit to the content of the leveling agent is 0.03 parts by weight, and a more preferable upper limit is 1 part by weight.
- the curable resin composition of the present invention preferably further contains a thixotropic agent.
- thixotropic agent examples include polysiloxane, polyacryl, polyamide, polyvinyl alcohol, polyetherester, alkyl-modified cellulose, peptide, polypeptide, silica and the like.
- the preferable lower limit of the content of the thixotropic agent is 0.1 parts by weight, and the preferable upper limit thereof is 5 parts by weight with respect to 100 parts by weight of the curable resin.
- the content of the thixotropy-imparting agent is within this range, the resulting curable resin composition is more excellent in coatability.
- a more preferable lower limit to the content of the thixotropic agent is 1 part by weight, and a more preferable upper limit is 3 parts by weight.
- the curable resin composition of the present invention preferably contains no solvent. By not containing the solvent, the resulting curable resin composition is excellent in low outgassing properties and does not require a solvent removal step.
- the curable resin composition of the present invention may contain various known additives such as curing retarders, reinforcing agents, viscosity modifiers and antioxidants, if necessary.
- the curable resin composition of the present invention preferably has a lower limit of 500 mPa ⁇ s and a preferred upper limit of viscosity measured at 25° C. using an E-type viscometer of 50,000 mPa ⁇ s. When the viscosity is within this range, the resulting curable resin composition will have excellent coatability.
- a more preferable lower limit of the viscosity is 1000 mPa ⁇ s, and a more preferable upper limit is 10,000 mPa ⁇ s.
- the above viscosity can be measured, for example, by using VISCOMETER TV-22 (manufactured by Toki Sangyo Co., Ltd.) as an E-type viscometer.
- 1 rotor can be measured at a rotational speed of 1 rpm or 10 rpm.
- the viscosity can be easily set within the above range by adjusting the contents of the cationically polymerizable polysilsesquioxane and the other cationically polymerizable compound.
- the curable resin composition of the present invention can be used for hard coating agents, sealing agents for displays, microlenses and the like. Among others, it is preferably used to protect and seal the optical semiconductor element or the like by forming a coating layer on the optical semiconductor element or the like, or by covering the optical semiconductor element or the like in a film form.
- a coating layer formed using the curable resin composition of the present invention is also one aspect of the present invention.
- a film formed using the curable resin composition of the present invention is also one aspect of the present invention.
- the coating layer of the present invention can be formed by applying the curable resin composition of the present invention onto an object to be coated such as an optical semiconductor element and then curing the composition.
- the film of the present invention can be formed by applying the curable resin composition of the present invention to a release film or the like and then curing the composition.
- Examples of methods for applying the curable resin composition of the present invention include a spin coating method, a bar coating method, an inkjet method, and the like.
- the curable resin composition of the present invention can be easily cured by light irradiation.
- Examples of the method of curing the curable resin composition of the present invention by light irradiation include a method of irradiating light with a wavelength of 300 nm or more and 400 nm or less and an integrated light amount of 300 mJ/cm 2 or more and 3000 mJ/cm 2 or less. .
- Examples of light sources for irradiating the curable resin composition of the present invention with light include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, excimer lasers, chemical lamps, black light lamps, microwave-excited mercury lamps, Examples include metal halide lamps, sodium lamps, halogen lamps, xenon lamps, LED lamps, fluorescent lamps, sunlight, and electron beam irradiation devices. These light sources may be used alone, or two or more of them may be used in combination. These light sources are appropriately selected according to the absorption wavelength of the photopolymerization initiator.
- Examples of means for irradiating the curable resin composition of the present invention with light include simultaneous irradiation with various light sources, sequential irradiation with a time lag, and combined irradiation of simultaneous and sequential irradiation. means may be used.
- the curable resin composition of the present invention may be cured by heating after the light irradiation.
- the curable resin composition which is excellent in the hardness of coloring property and hardened
- Examples 1 to 9 and Comparative Examples 1 and 2 The curable resin compositions of Examples 1 to 9 and Comparative Examples 1 and 2 were prepared by stirring and mixing each material using a stirring mixer according to the compounding ratio shown in Table 1.
- a stirring mixer Awatori Mixer ARE-310 (manufactured by Thinky Corporation) was used.
- the resulting curable resin composition was measured using an E-type viscometer (manufactured by Toki Sangyo Co., Ltd., "VISCOMETER TV-22"). No. 1 rotor was used, and the viscosity was measured under the conditions of 25° C. and a rotation speed of 1 rpm or 10 rpm. Table 1 shows the results.
- Each curable resin composition obtained in Examples and Comparative Examples was coated on a glass substrate provided with a gap using a Kapton tape using a bar coater No. 1. 5 (manufactured by AS ONE) to a thickness of 30 ⁇ m, and then irradiated with ultraviolet rays (wavelength: 365 nm) of 100 mW/cm 2 for 30 seconds using a metal halide lamp to photocure the curable resin composition. and obtained a test piece.
- the optical density (OD value) of the obtained test piece was measured using an optical densitometer (manufactured by X-rite, "Spectrometer").
- the curable resin composition which is excellent in the hardness of coloring property and hardened
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110124764A1 (en) * | 2008-06-10 | 2011-05-26 | Christoph Thalacker | Initiator system with biphenylene derivates, method of production and use thereof |
| WO2016204115A1 (ja) * | 2015-06-17 | 2016-12-22 | 株式会社ダイセル | 硬化物の製造方法、硬化物、及び前記硬化物を含む積層物 |
| WO2016203957A1 (ja) * | 2015-06-17 | 2016-12-22 | 株式会社ダイセル | 硬化性組成物、及び成形体 |
| WO2018037565A1 (ja) * | 2016-08-26 | 2018-03-01 | Jnc株式会社 | エポキシ樹脂組成物及び密着性に優れる低硬化収縮性樹脂硬化膜 |
| WO2018189945A1 (ja) * | 2017-04-12 | 2018-10-18 | 株式会社ダイセル | 硬化性組成物、硬化物及びハードコートフィルム |
| JP2018177952A (ja) * | 2017-04-12 | 2018-11-15 | 株式会社ダイセル | 硬化性組成物、硬化物及びハードコートフィルム |
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- 2022-09-29 JP JP2022562874A patent/JPWO2023054561A1/ja active Pending
- 2022-09-29 WO PCT/JP2022/036375 patent/WO2023054561A1/ja active Application Filing
- 2022-09-30 TW TW111137235A patent/TW202323461A/zh unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110124764A1 (en) * | 2008-06-10 | 2011-05-26 | Christoph Thalacker | Initiator system with biphenylene derivates, method of production and use thereof |
| WO2016204115A1 (ja) * | 2015-06-17 | 2016-12-22 | 株式会社ダイセル | 硬化物の製造方法、硬化物、及び前記硬化物を含む積層物 |
| WO2016203957A1 (ja) * | 2015-06-17 | 2016-12-22 | 株式会社ダイセル | 硬化性組成物、及び成形体 |
| WO2018037565A1 (ja) * | 2016-08-26 | 2018-03-01 | Jnc株式会社 | エポキシ樹脂組成物及び密着性に優れる低硬化収縮性樹脂硬化膜 |
| WO2018189945A1 (ja) * | 2017-04-12 | 2018-10-18 | 株式会社ダイセル | 硬化性組成物、硬化物及びハードコートフィルム |
| JP2018177952A (ja) * | 2017-04-12 | 2018-11-15 | 株式会社ダイセル | 硬化性組成物、硬化物及びハードコートフィルム |
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