CN111435220A - Photosensitive resin composition, optical film and method for producing same - Google Patents
Photosensitive resin composition, optical film and method for producing same Download PDFInfo
- Publication number
- CN111435220A CN111435220A CN201910035514.3A CN201910035514A CN111435220A CN 111435220 A CN111435220 A CN 111435220A CN 201910035514 A CN201910035514 A CN 201910035514A CN 111435220 A CN111435220 A CN 111435220A
- Authority
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- China
- Prior art keywords
- optical film
- photosensitive resin
- resin composition
- formula
- integer
- Prior art date
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- Granted
Links
- 239000012788 optical film Substances 0.000 title claims abstract description 62
- 239000011342 resin composition Substances 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 56
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 28
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000002834 transmittance Methods 0.000 claims abstract description 24
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005977 Ethylene Substances 0.000 claims abstract description 5
- 239000010408 film Substances 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 239000011248 coating agent Substances 0.000 claims description 13
- 238000000576 coating method Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 2
- -1 methacryloyl Chemical group 0.000 description 26
- 239000000654 additive Substances 0.000 description 9
- 230000035515 penetration Effects 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 8
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 8
- 239000012965 benzophenone Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical group C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- MWKAGZWJHCTVJY-UHFFFAOYSA-N 3-hydroxyoctadecan-2-one Chemical compound CCCCCCCCCCCCCCCC(O)C(C)=O MWKAGZWJHCTVJY-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 150000001767 cationic compounds Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 238000007607 die coating method Methods 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- TWAOQVMPIYQPKG-UHFFFAOYSA-N ethanone Chemical compound C[C+]=O TWAOQVMPIYQPKG-UHFFFAOYSA-N 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical class CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 150000004053 quinones Chemical class 0.000 description 2
- 239000011265 semifinished product Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- NTJCUGNAAPNLAQ-UHFFFAOYSA-N 1-(2-methylphenyl)-2-phenylpropan-1-one Chemical compound C=1C=CC=CC=1C(C)C(=O)C1=CC=CC=C1C NTJCUGNAAPNLAQ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- XOAKHODFHUHKSO-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C(C)C1=CC=2C(C3=CC=CC=C3SC2C(=C1)CC)=O.C(C)C1=CC=2C(C3=CC=CC=C3SC2C(=C1)CC)=O XOAKHODFHUHKSO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- WFKIYROFDWMUEO-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1.C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 WFKIYROFDWMUEO-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- MPAGVACEWQNVQO-UHFFFAOYSA-N 3-acetyloxybutyl acetate Chemical compound CC(=O)OC(C)CCOC(C)=O MPAGVACEWQNVQO-UHFFFAOYSA-N 0.000 description 1
- ARWGJPKPNJAQLC-UHFFFAOYSA-N CN(C1=CC=C(C(=O)C2=CC=C(C=C2)N(C)C)C=C1)C.C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.C(C)NCC Chemical compound CN(C1=CC=C(C(=O)C2=CC=C(C=C2)N(C)C)C=C1)C.C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.C(C)NCC ARWGJPKPNJAQLC-UHFFFAOYSA-N 0.000 description 1
- OWJSERUKNXOLKX-UHFFFAOYSA-N CN(C1=CC=C(C=C1)C(C)=O)C.CN(C1=CC=C(C=C1)C(C)=O)C Chemical compound CN(C1=CC=C(C=C1)C(C)=O)C.CN(C1=CC=C(C=C1)C(C)=O)C OWJSERUKNXOLKX-UHFFFAOYSA-N 0.000 description 1
- BXXRPOQKMLXLCV-UHFFFAOYSA-N COC1=CC=C(C(C)=O)C=C1.COC1=CC=C(C(C)=O)C=C1 Chemical compound COC1=CC=C(C(C)=O)C=C1.COC1=CC=C(C(C)=O)C=C1 BXXRPOQKMLXLCV-UHFFFAOYSA-N 0.000 description 1
- CILAUZHQJZCFEO-UHFFFAOYSA-N ClC(Cl)(Cl)C1=NC(=NC(=N1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl.ClC(Cl)(Cl)C1=NC(=NC(=N1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl Chemical compound ClC(Cl)(Cl)C1=NC(=NC(=N1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl.ClC(Cl)(Cl)C1=NC(=NC(=N1)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl CILAUZHQJZCFEO-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 101100464868 Homo sapiens PPIL1 gene Proteins 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 102100038802 Peptidyl-prolyl cis-trans isomerase-like 1 Human genes 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- MNCARFJUFRHXRC-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylcyclohexa-1,5-dien-1-yl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(C=1C=CC(C)(C)CC=1C)C(=O)C1=C(OC)C=CC=C1OC MNCARFJUFRHXRC-UHFFFAOYSA-N 0.000 description 1
- LOCXTTRLSIDGPS-FVDSYPCUSA-N [(z)-[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(/CCCCCC)=N\OC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-FVDSYPCUSA-N 0.000 description 1
- SEEVRZDUPHZSOX-UHFFFAOYSA-N [1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(C)=NOC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IWXWFPGJAZUXBL-UHFFFAOYSA-N naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1.C1=CC=C2C(=O)C=CC(=O)C2=C1 IWXWFPGJAZUXBL-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The invention provides a photosensitive resin composition capable of forming lower warping degree and high transmittance, an optical film and a manufacturing method thereof. The photosensitive resin composition comprises: (A) an ethylenically unsaturated group-containing compound having one or two aromatic rings; (B) a bisphenol fluorene oligomer having one or two (meth) acryloyl groups; and (C) a photoinitiator, wherein the weight ratio of the compound (A) containing ethylene unsaturated group to the bisphenol fluorene oligomer (B) is 0.50-0.95.
Description
Technical Field
The present invention relates to a resin composition, an optical film and a method for producing the same, and more particularly, to a photosensitive resin composition, an optical film and a method for producing the same.
Background
In recent years, thick film photosensitive compositions have been widely used, for example, in touch mobile devices, fingerprint recognition systems, and wafer packaging, but since thick film photosensitive compositions mostly contain an additive solvent, it is difficult to achieve a thickness of about 20 to 120 μm on a substrate, and problems such as low transmittance and high warpage tend to occur at a high film thickness.
In particular, the optical requirements of fingerprint recognition systems are more stringent, requiring thicker optical films as spacers and high transmittance for both infrared and visible light, however, there are many problems to be overcome in order to achieve high transmittance for both infrared and visible light at high film thickness (e.g., 120 μm), such as: the thick film causes problems such as warpage of the substrate, difficulty in achieving a thick viscosity of the photosensitive resin solution, difficulty in uniform surface coating, and cracking of the optical film after photo-curing.
From the above, it is known that those skilled in the art have been eagerly required to solve the problem of providing a photosensitive resin composition having desirable optical and mechanical properties at a film thickness of 20 μm to 120 μm.
Disclosure of Invention
Accordingly, the present invention provides a photosensitive resin composition capable of forming a film having a low warpage and a high transmittance, an optical film, and a method for manufacturing the same.
The invention provides a photosensitive resin composition, comprising: (A) an ethylenically unsaturated group-containing compound having one or two aromatic rings; (B) a bisphenol fluorene oligomer having one or two (meth) acryloyl groups; and (C) a photoinitiator. Wherein the weight ratio of the compound (A) containing ethylene unsaturated group to the bisphenol fluorene oligomer (B) is 0.50-0.95.
In an embodiment of the present invention, the photosensitive resin composition further includes (E) a solvent, and the content of the (E) solvent is 1 wt% or less of the photosensitive resin composition.
In an embodiment of the invention, the photosensitive resin composition does not contain a solvent.
In an embodiment of the invention, the compound (a) containing an ethylenically unsaturated group includes at least one selected from the group consisting of compounds represented by formulae (1) to (14).
In the formula (1), n1 and m1 are each independently an integer of 0 to 20, the sum of n1 and n2 is an integer of 1 to 20,
in the formula (2), n2 and m2 are each independently an integer of 0 to 4, the sum of n2 and m2 is an integer of 2 to 4,
in the formula (3), n3 is an integer of 0 to 3,
in the formula (4), R1An alkyl group having 1 to 20 carbon atoms,
in the formula (5), R2An alkyl group having 1 to 20 carbon atoms,
in the formula (6), R3An alkyl group having 1 to 20 carbon atoms,
in the formula (13), n4 is an integer of 1 to 3,
in the formula (14), n5 is an integer of 1 to 3.
In an embodiment of the present invention, the compound (a) containing an ethylenically unsaturated group includes a compound represented by formula (1).
In an embodiment of the present invention, the bisphenol fluorene oligomer (B) has a weight average molecular weight of 500-5000.
In one embodiment of the present invention, the viscosity of the photosensitive resin composition at 25 ℃ is 600 to 7000 mPas.
The invention also provides a manufacturing method of the optical film, which comprises the following steps: first, the photosensitive resin composition is applied to a substrate to form a coating film. Subsequently, the coating film is subjected to an exposure step. Then, the exposed coating film is subjected to a baking step to form an optical film on the substrate.
In an embodiment of the present invention, in the method for manufacturing an optical film, a wavelength of the exposure step is 200 to 500 nm.
In an embodiment of the invention, in the manufacturing method of the optical film, the temperature of the baking step is 130 ℃ to 280 ℃.
The present invention also provides an optical film prepared by the above method for manufacturing an optical film.
In an embodiment of the invention, the optical film has a transmittance of 85% or more for visible light with a wavelength of 380nm to 780nm when the thickness of the optical film is 20 to 120 μm.
In an embodiment of the invention, the optical film has a transmittance of 90% or more for infrared rays having a wavelength of 780nm to 1100nm when the thickness of the optical film is 20 to 120 μm.
In an embodiment of the invention, when the thickness of the optical film is 20 to 120 μm, the warpage of the optical film relative to the substrate is less than 0.25 mm.
In view of the above, when the photosensitive resin composition of the present invention uses the weight ratio of (a) the compound containing an ethylenically unsaturated group to (B) the bisphenol fluorene oligomer of 0.50 to 0.95, the optical film can have a low warpage and a high transmittance when the photosensitive resin composition is used in the optical film, thereby improving the problems of substrate warpage and insufficient transmittance caused by thick films.
In order to make the aforementioned and other features and advantages of the invention more comprehensible, embodiments accompanied with figures are described in detail below.
Detailed Description
Definition of
The terms "comprising," "having," and the like, unless expressly stated otherwise, are generally to be construed as open-ended as well as non-limiting.
In the absence of a specific recitation, singular terms include the plural (and vice versa). In addition, the word "about" preceding a value generally includes the particular value unless specifically stated otherwise. As used herein, the term "about" refers to a variation of a standard value of + -10%, unless otherwise stated or implied.
It should be understood that the order of steps or order of performing certain actions is immaterial so long as the invention remains operable. Further, two or more steps or actions may be performed simultaneously.
Hereinafter, acrylic acid and/or methacrylic acid is represented by (meth) acrylic acid, and acrylate and/or methacrylate is represented by (meth) acrylate; similarly, (meth) acryloyl represents acryloyl and/or methacryloyl.
< photosensitive resin composition >
The invention provides a photosensitive resin composition, which comprises (A) a compound containing ethylene unsaturated group, which has one or two aromatic rings; (B) a bisphenol fluorene oligomer having one or two (meth) acryloyl groups; and (C) a photoinitiator. In addition, if necessary, the photosensitive resin composition may further include (D) an additive, (E) a solvent, or a combination thereof. The respective components used in the photosensitive resin composition of the present invention will be described in detail below.
(A) Compounds containing ethylenically unsaturated groups
(A) The ethylenically unsaturated group-containing compound has one or two aromatic rings. The warpage of an optical film formed from the photosensitive resin composition can be reduced by introducing an aromatic ring into the ethylenically unsaturated group-containing compound (A), and when the number of aromatic rings contained in the ethylenically unsaturated group-containing compound (A) is more than two, the transmittance of the optical film is reduced.
In addition, (a) the ethylenically unsaturated group-containing compound is preferably a (meth) acryloyl group having one or two groups. Since both the (A) ethylenically unsaturated group-containing compound and the (B) bisphenol fluorene oligomer used in the present invention have a (meth) acryloyl group, the reaction rate is uniform and the partial hardening is not too fast, so that the transmittance of the optical film can be maintained.
Specifically, the ethylenically unsaturated group-containing compound (a) includes at least one selected from the group consisting of compounds represented by formulae (1) to (14).
In the formula (1), n1 and m1 are each independently an integer of 0 to 20, and the sum of n1 and n2 is an integer of 1 to 20.
In the formula (2), n2 and m2 are each independently an integer of 0 to 4, and the sum of n2 and m2 is an integer of 2 to 4.
In the formula (3), n3 is an integer of 0 to 3.
In the formula (4), R1Is an alkyl group having 1 to 20 carbon atoms.
In the formula (5), R2Is an alkyl group having 1 to 20 carbon atoms.
In the formula (6), R3Is an alkyl group having 1 to 20 carbon atoms.
In the formula (13), n4 is an integer of 1 to 3.
In the formula (14), n5 is an integer of 1 to 3.
Specific examples of the compound represented by the formula (1) include compounds represented by the formula (1-1).
Specific examples of the compound represented by the formula (2) include compounds represented by the formula (2-1).
Specific examples of the compound represented by the formula (3) include compounds represented by the formula (3-1).
Specific examples of the compound represented by the formula (4) include compounds represented by the formula (4-1).
Specific examples of the compound represented by the formula (5) include compounds represented by the formula (5-1).
Specific examples of the compound represented by the formula (6) include compounds represented by the formula (6-1).
Specific examples of the compound represented by the formula (13) include compounds represented by the formula (13-1).
Specific examples of the compound represented by the formula (14) include compounds represented by the formula (14-1).
The above-mentioned (A) ethylenically unsaturated group-containing compound preferably contains a compound represented by the formula (1), more preferably a compound represented by the formula (1-1). The transmittance of the optical film can be further increased by using the compound represented by formula (1).
(B) Bisphenol fluorene oligomer
(B) The bisphenol fluorene oligomer has one or two (meth) acryloyl groups. Since both the (A) ethylenically unsaturated group-containing compound and the (B) bisphenol fluorene oligomer used in the present invention have a (meth) acryloyl group, the reaction rate is uniform and the partial hardening is not too fast, so that the transmittance of the optical film can be maintained.
(B) The bisphenol fluorene oligomer is not particularly limited, and MIRAMER HR6100 (modified bisphenol fluorene diacrylate) and MIRAMER HR6200 (modified bisphenol fluorene diacrylate) manufactured by wemon co., L td, inc.
(A) The weight ratio of the compound containing an ethylenically unsaturated group to the bisphenol fluorene oligomer (B) may be 0.50 to 0.95, preferably 0.66 to 0.86. When the weight ratio of the compound containing ethylene unsaturated group (A) and the bisphenol fluorene oligomer (B) is in the above range, the optical film formed by the photosensitive resin composition has low warpage and high transmittance.
(B) The bisphenol fluorene oligomer may have a weight average molecular weight of 500 to 5000. When the weight average molecular weight of the bisphenol fluorene oligomer (B) is in the above range, the viscosity of the photosensitive resin composition can be further adjusted to a desired range.
(C) Photoinitiator
(C) The photoinitiator is not particularly limited, and examples thereof include acetophenone compounds (acetophenone), phenyl acetone compounds (phenyl ketone), diimidazole compounds (biimidazole), benzophenone compounds (benzophenone), acyloxime compounds (acyloxide), acylphosphine oxide compounds (acylphosphine oxide), α -dione compounds (α -dione), ketone alcohol compounds (acyloin), ketone alcohol ether compounds (acyloinher), quinone compounds (quinone), halogen compounds, peroxides, cationic compounds, and combinations thereof.
Examples of the acetophenone-based compound include p-dimethylaminoacetophenone (p-dimethylaminoacetophenone), α '-dimethoxyazoxyacetophenone (α' -dimethoxyazoxy-acetophenone), 2 '-dimethyl-2-phenylacetophenone (2, 2' -dimethyl-2-phenyl-acetophenone), p-methoxyacetophenone (p-methoxy-acetophenone), 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one), 2-phenyl-2-N, N-dimethylamine-1- (4-morpholinophenyl) -1-butanone (2-benzyl-2-N, N-dimethylamino-1- (4-morpholinophenyl) -1-butanone), and combinations thereof.
Examples of the phenylacetone-based compound include 1-hydroxycyclohexyl phenyl ketone (trade name: Irgacure 184, product of Ciba Specialty Chemicals), 2-hydroxy-2-methyl-1-phenyl-propan-1-one (trade name: DAROCUR 1173, product of Ciba Specialty Chemicals), 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] phenyl } -2-methyl-propan-1-one (2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) benzyl ] phenyl } -2-methyl-propan-1-one -1-one, trade name: IRGACURE 127, manufactured by nubuck corporation), or combinations thereof.
Examples of the diimidazole compound include 2,2 ' -bis (o-chlorophenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole (2,2 ' -bis (o-chlorophenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole), 2 ' -bis (o-fluorophenyl) -4,4,5,5 ' -tetraphenyldiimidazole (2,2 ' -bis (o-fluorophenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole), 2 ' -bis (o-methylphenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole (2,2 ' -bis (o-methylphenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole), 2 ' -bis (o-methoxyphenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole, 2 ' -bis (o-methoxyphenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole, 4 ', 5, 5' -tetraphenyldiimidazole (2,2 '-bis (o-methoxyphenyl) -4, 4', 5,5 '-tetraphenyldiimidazole), 2' -bis (o-ethylphenyl) -4,4 ', 5, 5' -tetraphenyldiimidazole (2,2 '-bis (o-ethylphenyl) -4, 4', 5,5 '-tetraphenyldiimidazole), 2' -bis (p-methoxyphenyl) -4,4 ', 5, 5' -tetraphenyldiimidazole (2,2 '-bis (p-methoxyphenyl) -4, 4', 5,5 '-tetraphenyldiimidazole), 2' -bis (2,2 ', 4, 4' -tetramethoxyphenyl) -4,4 ', 5, 5' -tetraphenyldiimidazole (2,2 ' -bis (2,2 ', 4,4 ' -tetramethylxyphenyl) -4,4 ', 5,5 ' -tetraphenyldiazole), 2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole (2,2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole), 2 ' -bis (2,4-dichlorophenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole (2,2 ' -bis (2,4-dichlorophenyl) -4,4 ', 5,5 ' -tetraphenyldiimidazole), or a combination thereof.
Examples of the benzophenone-based compound include Thioxanthone (Thioxanthone), 2, 4-diethylthioxanthone (2, 4-diethylthioxanthone), Thioxanthone-4-sulfone (Thioxanthone-4-sulfone), benzophenone (benzophenone)4,4 '-bis (dimethylamine) benzophenone (4, 4' -bis (dimethylamino) benzophenone), 4 '-bis (diethylamine) benzophenone (4, 4' -bis (dimethylamino) benzophenone), and a combination thereof.
As the acyloxime-based compound, there may be mentioned, for example, an alkanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9-hydro-carbazol-3-substituent ] -,1- (O-acetyloxime) (ethanone,1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -,1- (O-acetyloxime) such as "CGI-242" product produced by Ciba refinement), 1- (4-phenyl-thio-phenyl) -octane-1, 2-dione 2-oxime-oxy-benzoate (1- (4-phenyl-thio-phenyl) -octane-1, 2-dione 2-oxide-O-benzoate, such as "CGI-124" products manufactured by gasoline refining), ethanone,1- [9-ethyl-6- (2-chloro-4-benzyl-thio-benzoyl) -9-hydro-carbazol-3-substituent ] -,1- (oxy-acetyl oxime) (ethanone,1- [9-ethyl-6- (2-chloro-4-benzyl-thio-benzoyl) -9H-carbazol-3-yl ] -,1- (O-acyl oxime), manufactured by asahi electric company), or a combination thereof.
Examples of acylphosphine oxides (acylphosphine oxides) include 2,4, 6-trimethylbenzoyldiphenylphosphine oxide (2,4, 6-trimethy-benzoyldiphenylsilane oxide), bis- (2, 6-dimethoxybenzoyl) -2,4, 4-trimethylphenylphosphine oxide (bis- (2, 6-dimethy-benzoyi) -2,4, 4-trimethylbenzylphosphinoxide), Phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide (Phenylbis (2,4, 6-trimethylphenylzoyl) phosphine oxide), or a combination thereof.
α -diketone (α -diketone) compounds include benzil (benzil), acetyl (acetyl) or a combination thereof.
Examples of the ketol (acyloin) type compounds include benzoin (benzoin).
Examples of ketone alcohol ether (acyloinether) compounds include benzoin methyl ether (benzophenone), benzoin ethyl ether (benzophenone), benzoin isopropyl ether (benzophenone), or a combination thereof.
Examples of quinone compounds include anthraquinone (anthraquinone), 1,4-naphthoquinone (1,4-naphthoquinone), and combinations thereof.
Examples of the halogen compound include phenacyl chloride (phenacyl chloride), tribromomethyl phenyl sulfone (tribromomethyl phenyl sulfone), tris (trichloromethyl) -s-triazine (tris (trichloromethyl) -s-triazine), and a combination thereof.
Examples of the peroxide include di-tert-butyl peroxide (di-tert-butylperoxide).
Examples of the cationic compound include diazonium salts, iodonium salts, sulfonium salts, and combinations thereof.
(C) The photoinitiator is preferably 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-phenyl-2-N, N-dimethylamine-1- (4-morpholinophenyl) -1-butanone, 2,4, 6-trimethylbenzoyldiphenylphosphine oxide, phenylbis (2,4,6-trimethylbenzoyl) phosphine oxide, or a combination thereof.
The amount of the photoinitiator (C) is 0.05 to 40 parts by weight, preferably 0.1 to 20 parts by weight, more preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the ethylenically unsaturated group-containing compound (A). When the photoinitiator (C) is in the above range, the reactivity of the initiator can be sufficiently exerted.
(D) Additive agent
On the premise of not influencing the efficacy of the invention, the photosensitive resin composition of the invention can be further optionally added with (D) additives. (D) The additive is not particularly limited, and specifically, the (D) additive includes a fluorine-based surfactant, a silicone surfactant, a nonionic surfactant, a leveling agent, or a combination thereof.
Based on 100 parts by weight of (A) the ethylenically unsaturated group-containing compound, (D) the additive may be 0.005 to 0.015 parts by weight,
(E) solvent(s)
The photosensitive resin composition preferably does not contain any solvent. However, the photosensitive resin composition of the present invention may further optionally contain (E) a solvent without affecting the efficacy of the present invention. (E) The solvent is a solvent which can dissolve (A) the compound containing an ethylenically unsaturated group, (B) the bisphenol fluorene oligomer, (C) the photoinitiator, and (D) the additive, but does not react with the above components.
(E) The solvent is not particularly limited, and examples thereof include ethylene glycol monoalkylethers, ethylene glycol dialkyl ethers, ethylene glycol monoalkylether acetates, propylene glycol monoalkylethers, propylene glycol dialkyl ethers, propylene glycol monoalkylether acetates, diethylene glycol dialkyl ethers (e.g., diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, etc.), diethylene glycol monoalkylether acetates, dipropylene glycol monoalkylethers, dipropylene glycol dialkyl ethers, dipropylene glycol monoalkylether acetates, esters, ketones, amides, lactones, and the like. Specific examples of preferred solvents include: propylene glycol monomethyl ether acetate, diethylene glycol ethyl methyl ether, gamma-butyrolactone, N-methylpyrrolidinone, 1, 3-butanediol diacetate, or combinations thereof.
(E) The content of the solvent is 1 wt% or less of the photosensitive resin composition. When the content of the solvent (E) exceeds 1% by weight of the photosensitive resin composition, when the photosensitive resin composition is intended to form a thick coating film (having a thickness of 50 μm or more), the solvent is volatilized to easily generate bubbles in the coating film. Further, the photosensitive resin composition preferably does not contain any solvent.
< method for producing photosensitive resin composition >
The method which can be used for preparing the photosensitive resin composition is not particularly limited, and examples thereof include: a liquid photosensitive resin composition is obtained by stirring (A) an ethylenically unsaturated group-containing compound, (B) a bisphenol fluorene oligomer, and (C) a photoinitiator in a stirrer to uniformly mix the mixture in a solution state, and if necessary, adding (D) an additive, (E) a solvent or a combination thereof to uniformly mix the mixture.
The viscosity of the photosensitive resin composition of the present invention at 25 ℃ is preferably 600 to 7000 mPas.
< method for producing optical film >
The invention provides a manufacturing method of an optical film, which comprises the following steps: first, the photosensitive resin composition is applied to a substrate to form a coating film. Subsequently, the coating film is subjected to an exposure step. Then, the exposed coating film is subjected to a baking step to form an optical film on the substrate.
As a method for applying the photosensitive resin composition to a substrate, a spin coater (spin coater), a non-spin coating machine (spin coating machine), or a slit-die coating machine (slit-die coating machine) can be used, and a spin coater is preferred. When a spin coater is used, the rotation speed is 800 to 3500rpm, and the thickness of the formed coating film is 20 to 120 μm.
Examples of the substrate include a glass substrate, a sapphire substrate, and a silicon wafer substrate.
The light source in the exposure step may be ultraviolet rays such as g-line, h-line, i-line, etc. The apparatus for the exposure step is not particularly limited, and a high mercury lamp, an ultra-high mercury lamp, or a metal halide lamp may be used. The wavelength of the exposure step may be 200 to 500 nm.
The temperature of the baking step may be 130 ℃ to 280 ℃.
The optical film has a transmittance of 85% or more for visible light having a wavelength of 380nm to 780nm and a transmittance of 90% or more for infrared light having a wavelength of 780nm to 1100nm when the thickness of the optical film is 20 to 120 [ mu ] m. In addition, when the thickness of the optical film is 20-120 μm, the warping degree of the optical film relative to the substrate is less than 0.25 mm.
The present invention will be further described with respect to the following examples, but it should be understood that these examples are for illustrative purposes only and should not be construed as limiting the practice of the invention.
Photosensitive resin composition and examples of optical film
Examples 1 to 3 and comparative examples 1 to 2 of the photosensitive resin composition and the optical film are described below:
example 1
a. Photosensitive resin composition
The photosensitive resin composition of example 1 was prepared by mixing 38.80 wt% of (A) an ethylenically unsaturated group-containing compound, (B) 58.20 wt% of bisphenol fluorene oligomer (B), and 3 wt% of 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (Brilliant 907(IRGACURE 907), manufactured by BASF, Japan) with stirring uniformly.
b. Optical film
Each of the photosensitive resin compositions obtained in the examples was coated on a silicon wafer substrate by spin coating (spin coater model MK-VIII, manufactured by Tokyo Electron L imitations, TE L, rotation speed 1000rpm, Tokyo Power Co., Ltd.). subsequently, 1600J/m was used2Is exposed to ultraviolet light (exposure machine model 5500iZa, manufactured by Canon corporation) to form a semi-finished product. Then, the resultant was baked at 220 ℃ for 20 minutes to obtain an optical film. The obtained semi-finished product and the optical film were evaluated in the following evaluation methods, and the results are shown in table 1.
Examples 2 to 3 and comparative examples 1 to 2
The photosensitive resin compositions of examples 2 to 3 and comparative examples 1 to 2 were prepared in the same procedure as in example 1, and they were different in that: the types of components and the amounts of the components used in the photosensitive resin composition were changed (as shown in table 1). The obtained photosensitive resin compositions were evaluated in the following evaluation methods, and the results are shown in table 1.
TABLE 1
< evaluation mode >
a. Film thickness
The film thickness of the semi-finished optical film was measured by an optical film thickness meter (model VM-1210, manufactured by Dainippon Seiko Co., Ltd.).
◎ film thickness of 20-120 μm
Gamma rays: the film thickness is less than 20 mu m
b. Degree of warp
The warp was measured by inserting a thickness gauge (model 25410015, manufactured by Phoenix electronics, Germany) into the edge of the substrate and measuring the thickness of the gap between the edge and the flat surface of the substrate. Warpage was evaluated in the following manner.
◎ warping degree < 0.25mm
△ warpage < 0.3mm ≦ 0.25mm
Gamma rays: warping degree of 0.3mm <
c. Degree of penetration of visible light
The transmittance of the optical film at a wavelength of 380nm to 780nm was measured by an ultraviolet-visible spectrophotometer (model U2900, manufactured by Hitachi, Ltd.).
◎ 85% less penetration
△, 80% and less than 85% penetration
Gamma rays: the penetration degree is less than 80 percent
d. Degree of penetration of infrared ray
The transmittance of the optical film at a wavelength of 780nm to 1100nm was measured by an ultraviolet-visible spectrophotometer (model U2900, manufactured by Hitachi, Ltd.).
◎ penetration is 98% ≦ penetration
△, 80% and less than 98% penetration
Gamma rays: the penetration degree is less than 80 percent
e. Re-coatability
About 100mm ink marks were brushed on the optical film using a dyne pen of ACCU, USA, and it was observed whether more than 90% of the ink marks shrunk within 2 seconds to form ink drops until they did not shrink and are dynes thereof.
◎ surface tension of < 38 dyne/cm ≦ surface tension
Gamma rays: surface tension of less than 38 dynes/cm
< evaluation results >
As is clear from Table 1, the photosensitive resin compositions (examples 1 to 3) using (B) bisphenol fluorene oligomers and having a weight ratio of (A) the compound having an ethylenically unsaturated group to (B) the bisphenol fluorene oligomers of 0.50 to 0.95 have good recoatability, and not only can form films having a thickness of 20 μm to 120 μm, but also optical films formed therefrom have low warpage and high transmittance in visible light and infrared light.
On the other hand, the photosensitive resin composition (comparative example 1) in which the weight ratio of (a) the ethylenically unsaturated group-containing compound to (B) the bisphenol fluorene oligomer is more than 0.95 failed to form a film having a thickness of 20 μm to 120 μm, and the formed optical film had a high warp degree.
In addition, the optical film formed from the photosensitive resin composition (comparative example 2) in which the bisphenol fluorene oligomer (B) was replaced by the epoxy acrylic oligomer (B') had a high warping degree and had insufficient transmittance in visible light and infrared light.
In summary, when the photosensitive resin composition of the present invention comprises the compound containing the ethylenically unsaturated group and the specific bisphenol fluorene oligomer, and the weight ratio of the compound containing the ethylenically unsaturated group to the bisphenol fluorene oligomer is 0.50 to 0.95, the optical film formed by the photosensitive resin composition has a lower warpage and a high transmittance, thereby improving the problems of substrate warpage and insufficient transmittance caused by thick films.
Although the present invention has been described with reference to the above embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention.
Claims (14)
1. A photosensitive resin composition comprising:
(A) an ethylenically unsaturated group-containing compound having one or two aromatic rings;
(B) a bisphenol fluorene oligomer having one or two (meth) acryloyl groups; and
(C) a photo-initiator,
wherein the weight ratio of the compound (A) containing ethylene unsaturated group to the bisphenol fluorene oligomer (B) is 0.50-0.95.
2. The photosensitive resin composition according to claim 1, further comprising (E) a solvent, wherein the content of the (E) solvent is 1% by weight or less of the photosensitive resin composition.
3. The photosensitive resin composition according to claim 1, wherein the photosensitive resin composition does not contain a solvent.
4. The photosensitive resin composition according to claim 1, wherein the (A) ethylenically unsaturated group-containing compound comprises at least one member selected from the group consisting of compounds represented by the formulae (1) to (14),
in the formula (1), n1 and m1 are each independently an integer of 0 to 20, the sum of n1 and n2 is an integer of 1 to 20,
in the formula (2), n2 and m2 are each independently an integer of 0 to 4, the sum of n2 and m2 is an integer of 2 to 4,
in the formula (3), n3 is an integer of 0 to 3,
in the formula (4), R1An alkyl group having 1 to 20 carbon atoms,
in the formula (5), R2An alkyl group having 1 to 20 carbon atoms,
in the formula (6), R3An alkyl group having 1 to 20 carbon atoms,
in the formula (13), n4 is an integer of 1 to 3,
in the formula (14), n5 is an integer of 1 to 3.
5. The photosensitive resin composition according to claim 4, wherein the (A) ethylenically unsaturated group-containing compound comprises a compound represented by formula (1).
6. The photosensitive resin composition according to claim 1, wherein the (B) bisphenol fluorene oligomer has a weight average molecular weight of 500 to 5000.
7. The photosensitive resin composition according to claim 1, wherein the viscosity of the photosensitive resin composition at 25 ℃ is 600 to 7000 mPas.
8. A method of manufacturing an optical film, comprising
Applying the photosensitive resin composition according to any one of claims 1 to 7 to a substrate to form a coating film;
the coating film is subjected to an exposure step,
subjecting the exposed coating film to a baking step to form an optical film on the substrate.
9. The method for producing an optical film according to claim 8, wherein the wavelength in the exposure step is 200 to 500 nm.
10. The method of manufacturing an optical film according to claim 8, wherein the temperature of the baking step is 130 ℃ to 280 ℃.
11. An optical film produced by the method for producing an optical film according to any one of claims 8 to 10.
12. The optical film according to claim 11, wherein the optical film has a transmittance of 85% or more for visible light having a wavelength of 380nm to 780nm at a thickness of 20 to 120 μm.
13. The optical film according to claim 11, wherein the optical film has a transmittance of 90% or more for infrared rays having a wavelength of 780nm to 1100nm at a thickness of 20 to 120 μm.
14. The optical film according to claim 11, wherein when the thickness of the optical film is 20 to 120 μm, the warp of the optical film relative to the substrate is less than 0.25 mm.
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| CN111435220B (en) | 2024-02-27 |
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