CN111435220B - Photosensitive resin composition, optical film, and method for producing same - Google Patents
Photosensitive resin composition, optical film, and method for producing same Download PDFInfo
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- CN111435220B CN111435220B CN201910035514.3A CN201910035514A CN111435220B CN 111435220 B CN111435220 B CN 111435220B CN 201910035514 A CN201910035514 A CN 201910035514A CN 111435220 B CN111435220 B CN 111435220B
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- Prior art keywords
- optical film
- photosensitive resin
- resin composition
- formula
- unsaturated group
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- 239000011342 resin composition Substances 0.000 title claims abstract description 59
- 239000012788 optical film Substances 0.000 title claims abstract description 58
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 56
- -1 acryl groups Chemical group 0.000 claims abstract description 34
- 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
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 239000010408 film Substances 0.000 claims description 29
- 239000000758 substrate Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 238000002834 transmittance Methods 0.000 claims description 19
- 239000011248 coating agent Substances 0.000 claims description 15
- 238000000576 coating method Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 230000035515 penetration Effects 0.000 description 12
- 239000000654 additive Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000007670 refining Methods 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000243 solution Substances 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
- 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 2
- MWKAGZWJHCTVJY-UHFFFAOYSA-N 3-hydroxyoctadecan-2-one Chemical compound CCCCCCCCCCCCCCCC(O)C(C)=O MWKAGZWJHCTVJY-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-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
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 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
- QPOIJJUKCPCQIV-UHFFFAOYSA-N diphenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 QPOIJJUKCPCQIV-UHFFFAOYSA-N 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
- 150000002366 halogen compounds 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
- 239000000047 product Substances 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
- 238000003756 stirring Methods 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
- 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
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-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
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical compound C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-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
- 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
- PDQYOPNIPOWAFS-UHFFFAOYSA-N 2-hydroxyiminopropanal Chemical compound O=CC(C)=NO PDQYOPNIPOWAFS-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
- LWRBVKNFOYUCNP-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 LWRBVKNFOYUCNP-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
- 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 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- DHQGJRUPGCOUBR-UHFFFAOYSA-N C(C)N(C1=CC=C(C(=O)C2=CC=C(C=C2)N(CC)CC)C=C1)CC.C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.C(C)NCC Chemical compound C(C)N(C1=CC=C(C(=O)C2=CC=C(C=C2)N(CC)CC)C=C1)CC.C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.C(C)NCC DHQGJRUPGCOUBR-UHFFFAOYSA-N 0.000 description 1
- XHIKSLHIZYVEQI-UHFFFAOYSA-N CC1=C(C(=O)[PH2]=O)C(=CC(=C1)C)C Chemical compound CC1=C(C(=O)[PH2]=O)C(=CC(=C1)C)C XHIKSLHIZYVEQI-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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 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
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 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
- 150000008062 acetophenones Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 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
- 238000007607 die coating method Methods 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers 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
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- 238000004806 packaging method and process Methods 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 229930015704 phenylpropanoid Natural products 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
- 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
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention provides a photosensitive resin composition, an optical film and a manufacturing method thereof, wherein the photosensitive resin composition has low warping degree and high penetrability. The photosensitive resin composition comprises: (A) An ethylenically unsaturated group-containing compound having one or two aromatic rings; (B) Bisphenol fluorene oligomer having one or two (meth) acryl groups; and (C) a photoinitiator, wherein the weight ratio of the (A) ethylenically unsaturated group-containing compound to the (B) bisphenol fluorene oligomer is 0.50 to 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-sensitive mobile devices, fingerprint recognition systems, and wafer packaging, and generally thick film photosensitive compositions are mostly added with solvents, so that 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 are likely to occur at a high film thickness.
Particularly, the optical requirements of fingerprint recognition systems are more stringent, and thicker optical films are required as spacers, and at the same time, high transmittance to both infrared and visible light is required, however, there are many problems to be overcome in order to achieve high transmittance to both infrared and visible light at a high film thickness (for example, 120 μm thickness), such as: the thick film causes problems such as warpage of the substrate, difficulty in achieving the viscosity of the photosensitive resin solution, difficulty in uniform surface coating, and cracking of the optical film after photo hardening.
From the above, it is an urgent need for a solution to the present art to provide a photosensitive resin composition having desirable optical and mechanical properties at a film thickness of 20 μm to 120 μm.
Disclosure of Invention
In view of the above, the present invention provides a photosensitive resin composition, an optical film, and a method for producing the same, which can form a film having a low degree of warpage and a high degree of penetration.
The present invention provides a photosensitive resin composition, comprising: (A) An ethylenically unsaturated group-containing compound having one or two aromatic rings; (B) Bisphenol fluorene oligomer having one or two (meth) acryl groups; and (C) a photoinitiator. Wherein the weight ratio of the (A) ethylenically unsaturated group-containing compound to the (B) bisphenol fluorene oligomer is 0.50 to 0.95.
In an embodiment of the present invention, the photosensitive resin composition further contains (E) a solvent, wherein the content of (E) the 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 above (a) ethylenically unsaturated group-containing compound includes at least one selected from the group consisting of the compounds represented by the formulas (1) to (14).
In the formula (1), n1 and m1 are each independently integers of 0 to 20, the sum of n1 and m1 is an integer of 1 to 20,
in the formula (2), n2 and m2 are each independently integers 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), R 1 Is alkyl with 1-20 carbon atoms,
in the formula (5), R 2 Is alkyl with 1-20 carbon atoms,
in the formula (6), R 3 Is alkyl with 1-20 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 one embodiment of the present invention, the above (a) ethylenically unsaturated group-containing compound includes a compound represented by formula (1).
In an embodiment of the invention, the weight average molecular weight of the bisphenol fluorene oligomer (B) is 500 to 5000.
In one embodiment of the present invention, the viscosity of the photosensitive resin composition is 600 to 7000 mPas at 25 ℃.
The invention also provides a method for manufacturing the optical film, which comprises the following steps: first, the photosensitive resin composition is applied to a substrate to form a coating film. Next, 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 invention, in the method for manufacturing an optical film, a wavelength of the exposing step is 200-500 nm.
In an embodiment of the invention, the temperature of the baking step is 130 ℃ to 280 ℃.
The invention also provides an optical film prepared by the method for manufacturing the optical film.
In an embodiment of the invention, the optical film has a transmittance of 85% or more for visible light having a wavelength of 380nm to 780nm when the thickness 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 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 with respect to the substrate is less than 0.25mm.
Based on the above, the photosensitive resin composition of the present invention uses (a) the vinyl unsaturated group-containing compound and (B) the bisphenol fluorene oligomer in a weight ratio of 0.50 to 0.95, and when the photosensitive resin composition is used in an optical film, the optical film can have a low warpage and a high transmittance, thereby improving the problem that a thick film causes warpage of a substrate and insufficient transmittance.
In order to make the above features and advantages of the present invention more comprehensible, embodiments accompanied with figures are described in detail below.
Detailed Description
Definition of the definition
The terms "comprising," "having," and the like, are generally understood to be open-ended and not limited to, unless expressly stated otherwise.
Unless specifically stated otherwise, singular terms include plural (and vice versa). In addition, the term "about" preceding a numerical value generally includes the particular numerical value unless specifically stated otherwise. Here, the term "about" refers to a variation of + -10% of the standard value, unless otherwise specified or implied.
It should be understood that the order of steps or order in which certain actions are performed is not important so long as the present invention remains operable. Furthermore, two or more steps or actions may be performed simultaneously.
Hereinafter, acrylic acid and/or methacrylic acid are denoted by (meth) acrylic acid, and acrylic acid ester and/or methacrylic acid ester are denoted by (meth) acrylic acid ester; similarly, acryl and/or methacryl is represented by (meth) acryl.
< photosensitive resin composition >
The present invention provides a photosensitive resin composition comprising (A) a compound containing an ethylenic unsaturated group having one or two aromatic rings; (B) Bisphenol fluorene oligomer having one or two (meth) acryl groups; and (C) a photoinitiator. In addition, the photosensitive resin composition may further include (D) an additive, (E) a solvent, or a combination thereof, if necessary. The respective components used in the photosensitive resin composition of the present invention will be described in detail below.
(A) Compounds containing ethylenic unsaturation
(A) The ethylenically unsaturated group-containing compound has one or two aromatic rings. By introducing an aromatic ring into the compound (A) containing an ethylenic unsaturated group, the warpage of an optical film formed from the photosensitive resin composition can be reduced, and when the compound (A) containing an ethylenic unsaturated group contains more than two aromatic rings, the penetration of the optical film is reduced.
In addition, (A) the ethylenically unsaturated group-containing compound is preferably a compound having one or two (meth) acryloyl groups. The (a) ethylenically unsaturated group-containing compound and the (B) bisphenol fluorene oligomer used in the present invention each have a (meth) acryloyl group, and thus the reaction rate is uniform, and they are not locally hardened too fast, so that the penetration of the optical film can be maintained.
Specifically, the above-mentioned (a) ethylenically unsaturated group-containing compound contains at least one selected from the group consisting of compounds represented by the formulas (1) to (14).
In the formula (1), n1 and m1 are each independently integers of 0 to 20, and the sum of n1 and m1 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), R 1 Is an alkyl group having 1 to 20 carbon atoms.
In the formula (5), R 2 Is an alkyl group having 1 to 20 carbon atoms.
In the formula (6), R 3 Is 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 the compound 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 is preferably a compound comprising the compound represented by the formula (1), more preferably a compound represented by the formula (1-1). The penetration of the optical film can be further increased by using the compound represented by formula (1).
(B) Bisphenol fluorene oligomer
(B) Bisphenol fluorene oligomer has one or two (meth) acryl groups. The (a) ethylenically unsaturated group-containing compound and the (B) bisphenol fluorene oligomer used in the present invention each have a (meth) acryloyl group, and thus the reaction rate is uniform, and they are not locally hardened too fast, so that the penetration of the optical film can be maintained.
(B) The bisphenol fluorene oligomer is not particularly limited, and MIRAMER HR6100 (modified bisphenol fluorene diacrylate), MIRAMER HR6200 (modified bisphenol fluorene diacrylate) manufactured by Weiyuan commercial Co., ltd.
(A) The weight ratio of the ethylenically unsaturated group-containing compound to the bisphenol fluorene oligomer (B) may be 0.50 to 0.95, preferably 0.66 to 0.86. When the weight ratio of (A) the ethylenically unsaturated group-containing compound to (B) the bisphenol fluorene oligomer is within the above range, the optical film formed from the photosensitive resin composition can have a low degree of warpage and a high degree of penetration.
(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 within the above-mentioned range, the viscosity of the photosensitive resin composition can be further made within a desired range.
(C) Photoinitiator
(C) The photoinitiator is not particularly limited, and examples thereof include acetophenone-based compounds (acetothene), phenyl acetone-based compounds (phenyl ketone), diimidazole-based compounds (bisimidazole), benzophenone (benzophenone) -based compounds (bisoxime), acylphosphine oxides (acylphosphine oxide), α -diketones (α -diketene) -based compounds, ketols (acyloin) -based compounds, ketols ethers (acylointher) -based compounds, quinones (quinone) -based compounds, halogen compounds, peroxides, cationic-based compounds, and combinations thereof.
Examples of acetophenone compounds include p-dimethylaminoacetophenone (p-dimethylacetophenone), α '-dimethoxyazoxyacetophenone (α, α' -dimethylazoxy-acetogenine), 2 '-dimethyl-2-phenylacetophenone (2, 2' -dimethyl-2-phenyl-acetogenine), p-methoxyacetophenone (p-methoxy-acetogenine), 2-methyl-1- (4-methylsulfanyl) -2-morpholinopropane-1-one (2-methyl-1- (4-methylsulfanyl) -2-morpholino-1-propanone), 2-phenyl-2-N, N-dimethylamine-1- (4-morpholinophenyl) -1-butanone (2-benzyl-2-N, N-dimethylacetophenone) -1-butanone), or combinations thereof.
Examples of the phenylpropanoid compound include 1-hydroxycyclohexyl phenyl ketone (trade name: irgacure 184, manufactured by Ciba refining (Ciba Specialty Chemicals)), 2-hydroxy-2-methyl-1-phenyl-propane-1-one (trade name: DAROCUR 1173, manufactured by Ciba refining), 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl ] phenyl } -2-methyl-propane-1-one (2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propinyl) benzyl ] -phenyl } -2-methyl-propane-1-one, trade name: IRGACURE 127, manufactured by Ciba refining), and combinations thereof.
Examples of the bisimidazole compound include 2,2' -bis (o-chlorophenyl) -4,4', 5' -tetraphenylbisimidazole (2, 2' -bis (o-chlorophenyl) -4,4', 5' -tetraphenylbisimidazole), 2' -bis (o-fluorophenyl) -4, 5' -tetraphenylbisimidazole (2, 2' -bis (o-fluorophenyl) -4,4',5,5' -tetraphenyl-biimidozole), 2' -bis (o-methylphenyl) -4,4', 5' -tetraphenyl diimidazole (2, 2' -bis (o-methyl phenyl) -4,4', 5' -tetraphenyl-biimidozole), 2' -bis (o-methoxyphenyl) -4,4',5,5' -tetraphenyldiimidazole (2, 2' -bis (o-methoxyphenyl) -4,4', 5' -tetraphenylyl-biimidozole), 2' -bis (o-ethylphenyl) -4,4', 5' -tetraphenyldiimidazole (2, 2' -bis (o-ethylphenyl) -4,4', 5' -tetraphenylyl-biimidozole), 2' -bis (p-methoxyphenyl) -4,4',5,5' -tetraphenyl diimidazole (2, 2' -bis (p-methoxyphenyl) -4,4', 5' -tetraphenyl-biimidozole), 2' -bis (2, 2', 4' -tetramethoxyphenyl) -4,4', 5' -tetraphenyl diimidazole (2, 2',4,4' -tetramethoxyphenyl) -4,4', 5' -tetraphenyl-biimidozole, 2' -bis (2-chlorophenyl) -4,4', 5' -tetraphenyldiimidazole (2, 2' -bis (2-chlorophenyl) -4,4',5,5' -tetraphenyl-biimidozole), 2' -bis (2, 4-dichlorophenyl) -4,4', 5' -tetraphenyl diimidazole (2, 2' -bis (2, 4-dichlorophenyl) -4,4', 5' -tetraphenyl-biimidozole), or combinations thereof.
Examples of the benzophenone (benzophenone) compound include Thioxanthone (Thioxanthone), 2, 4-diethylthioxanthone (2, 4-diethylthioxanthone), thioxanthone-4-sulfone (Thioxanthone-4-sulfolane), benzophenone (benzophenone) 4,4'-bis (dimethylamine) benzophenone (4, 4' -bis (dimethylamino) benzophone), 4'-bis (diethylamine) benzophenone (4, 4' -bis (diethylamino) benzophenone), and combinations thereof.
As the acyloxy compound, there may be mentioned ethanone,1- [9-ethyl-6- (2-methylbenzoyl) -9-hydro-carbazole-3-substituent ] -,1- (oxo-acetoxime) (ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -,1- (O-acyloxime), such as "CGI-242" product manufactured by Ciba-refining), 1- (4-phenyl-thio-phenyl) -octane-1, 2-dione 2-oxime-oxo-benzoate (1- (4-phenyl-thio-phenyl) -octane-1, 2-dion-2-oxame-O-benzoate, such as "CGI-124" product manufactured by Ciba-refining), ethanone,1- [9-ethyl-6- (2-chloro-4-benzyl-thio-benzoyl) -9-hydro-carbazole-3-substituent ] -,1- (4-phenyl) -oxo-1, 2-dimethyl-2-oxamide, or a combination thereof.
Examples of the acylphosphine oxide (acylphosphine oxide) include 2,4,6-trimethylbenzoyl diphenylphosphine oxide (2, 4, 6-trimethylbenzoyl-benzoyldiphenyl phosphineoxide), bis- (2, 6-dimethoxybenzoyl) -2, 4-trimethylphenylphosphine oxide (bis- (2, 6-dimethoxyphenyl) -2, 4-trimethylphosphinidenephosphine oxide), phenylbis- (2, 4, 6-trimethylbenzoyl) phosphine oxide (phenyllbis (2, 4, 6-trimethylbenzoyl) phosphine oxide), and combinations thereof.
Examples of the α -diketone (α -diketone) compound include benzil (benzol), acetyl (acetyl), and combinations thereof.
Examples of the ketone alcohol (acyloin) compound include benzophenone (benzoin).
Examples of the ketone alcohol ether (acyloinnether) compound include benzophenone methyl ether (benzoin methylether), benzophenone ethyl ether (benzoineethyl ether), benzophenone isopropyl ether (benzoin isopropyl ether), and combinations thereof.
Examples of quinone compounds include anthraquinone (anthraquinone), 1,4-naphthoquinone (1, 4-naphthoquinone), and combinations thereof.
As the halogen compound, benzoyl methyl chloride (phenacyl chloride), tribromomethyl phenyl sulfone (tribromomethyl phenylsulfone), tris (trichloromethyl) -s-triazine (tris (trichloromethyl) -s-triazine), or a combination thereof can be exemplified.
The peroxide may be di-tert-butyl peroxide (di-tert-butyl peroxide).
The cationic compound may be diazonium salts, iodonium salts, sulfonium salts, or combinations thereof.
(C) The photoinitiator is preferably 2-methyl-1- (4-methylsulfanyl) -2-morpholinopropane-1-one, 2-phenyl-2-N, N-dimethylamine-1- (4-morpholinophenyl) -1-butanone, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide, or a combination thereof.
The photoinitiator (C) may be present in an amount of 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 (A) ethylenically unsaturated group-containing compound. When the photo initiator (C) is in the above range, the reactivity of the initiator can be sufficiently exhibited.
(D) Additive agent
The photosensitive resin composition of the present invention may further optionally contain (D) additives without affecting the efficacy of the present invention. (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) a compound containing an ethylenic unsaturated group, (B) a bisphenol fluorene oligomer, (C) a photoinitiator, and (D) an additive, but does not react with the above components.
(E) The solvent is not particularly limited, and examples thereof include ethylene glycol monoalkyl ethers, ethylene glycol dialkyl ethers, ethylene glycol monoalkyl ether acetates, propylene glycol monoalkyl ethers, propylene glycol dialkyl ethers, propylene glycol monoalkyl ether acetates, diethylene glycol dialkyl ethers (for example, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, etc.), diethylene glycol monoalkyl ether acetates, dipropylene glycol monoalkyl ethers, dipropylene glycol dialkyl ethers, dipropylene glycol monoalkyl ether acetates, esters, ketones, amides, lactones, etc. Specific examples of preferred solvents include: propylene glycol monomethyl ether acetate, diethylene glycol ethyl methyl ether, gamma-butyrolactone, N-methylpyrrolidone, 1, 3-butanediol diacetate, or combinations thereof.
(E) The content of the solvent is 1% by weight or less of the photosensitive resin composition. When the content of the solvent (E) exceeds 1% by weight or more of the photosensitive resin composition, bubbles are easily generated in the coating film by volatilization of the solvent when the photosensitive resin composition is intended to form a thick film (thickness 50 μm or more) coating. In addition, the photosensitive resin composition preferably does not contain any solvent. < method for producing photosensitive resin composition >
The method that can be used to prepare the photosensitive resin composition is not particularly limited, for example: the liquid photosensitive resin composition can be obtained by placing (A) an ethylenically unsaturated group-containing compound, (B) a bisphenol fluorene oligomer, and (C) a photoinitiator in a stirrer and stirring them to uniformly mix them into a solution state, and if necessary, adding (D) an additive, (E) a solvent, or a combination thereof, and uniformly mixing them.
The viscosity of the photosensitive resin composition of the present invention is preferably 600 to 7000 mPas at 25 ℃.
< 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. Next, 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.
The photosensitive resin composition may be applied to the substrate by a spin coater, a non-spin coater (spin loess coating machine) or a slit coater (slit-die coating machine), preferably a spin coater. In the case of using a spin coater, the rotation speed is 800 to 3500rpm, and the thickness of the formed coating film is 20 to 120. Mu.m.
The substrate may be a glass substrate, a sapphire substrate, or a silicon wafer substrate.
The light source of the exposure step can be ultraviolet rays such as g line, h line, i line and the like. The apparatus for the exposure step is not particularly limited, and a high mercury lamp, an ultra-high mercury lamp, or a metal halogen lamp may be mentioned. The wavelength of the exposure step may be 200 to 500nm.
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. When the thickness of the optical film is 20 to 120. Mu.m, the warp of the optical film with respect to the substrate is less than 0.25mm.
The present invention will be further described with respect to the following examples, but it should be understood that the examples are for illustrative purposes only and should not be construed as limiting the practice of the invention.
Examples of photosensitive resin compositions and optical films
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% by weight of (a) an ethylenically unsaturated group-containing compound, 58.20% by weight of (B) a bisphenol fluorene oligomer, and 3% by weight of 2-methyl-1- (4-methylsulfanyl) -2-morpholinopropane-1-one (manufactured by BASF) japan corporation, brilliant solid 907 (IRGACURE 907)) and stirring the mixture uniformly with a stirrer.
b. Optical film
The various photosensitive resin compositions obtained in the examples were applied to a silicon wafer substrate by spin coating (spin coater model MK-VIII, manufactured by Tokyo Wisco Co., ltd. (Tokyo Electron Limited, TEL), at 1000 rpm). Next, 1600J/m is utilized 2 Is exposed to ultraviolet light (model number 5500 for exposure iZa, manufactured by Canon, inc.) to form a semi-finished product. Then, baking was performed at 220℃for 20 minutes to obtain an optical film. The obtained semi-finished product and optical film were evaluated in the following evaluation manners, 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 the components and the amounts thereof used of the photosensitive resin compositions were changed (as shown in Table 1). The obtained photosensitive resin compositions were evaluated in the following evaluation manners, 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 Dain Seiko Co., ltd.).
And (3) the following materials: the film thickness is between 20 μm and 120 μm
And (3) the following steps: film thickness less than 20 mu m
b. Warp degree
The thickness of the gap between the substrate edge and the plane was measured as warpage by inserting a thickness gauge (model 25410015, manufactured by Phoenix electronics, germany) into the substrate edge. The warpage was evaluated in the following manner.
And (3) the following materials: the warpage is less than 0.25mm
Delta: warpage of 0.25mm or less and less than 0.3mm
And (3) the following steps: warp of 0.3mm <
c. Visible light transmittance
The transmittance of the optical film at a wavelength of 380nm to 780nm was measured by an ultraviolet-visible light spectrometer (model U2900, manufactured by Hitachi (Hitachi Co., ltd.).
And (3) the following materials: 85% or less penetration
Delta: the penetration is more than or equal to 80% and less than 85%
And (3) the following steps: penetration is less than 80%
d. Transmittance of infrared ray
The transmittance of the optical film at a wavelength of 780nm to 1100nm was measured by an ultraviolet-visible light spectrometer (model U2900, manufactured by Hitachi (Hitachi Co., ltd.).
And (3) the following materials: penetration of 98% +.
Delta: the penetration is more than or equal to 80% and less than 98%
And (3) the following steps: penetration is less than 80%
e. Recoatability of coating
The optical film was brushed with about 100mm ink marks using a dyne pen from ACCU corporation in the united states and observed for more than 90% of the ink marks shrinking to form ink drops within 2 seconds until no shrinkage and a factor of the shrinkage were reached.
And (3) the following materials: 38 dyne/cm +.
And (3) the following steps: surface tension < 38 dyne/cm
< evaluation results >
As is clear from Table 1, the photosensitive resin compositions (examples 1 to 3) using (B) bisphenol fluorene oligomer and having a weight ratio of (A) compound containing ethylenic unsaturated groups to (B) bisphenol fluorene oligomer of 0.50 to 0.95 have good recoatability, and not only can form films having a film thickness of 20 μm to 120 μm, but also can form optical films having a low warpage and high transmittance in visible light and infrared rays.
In contrast, the photosensitive resin composition (comparative example 1) having a weight ratio of (a) the ethylenically unsaturated group-containing compound to (B) the bisphenol fluorene oligomer of more than 0.95 failed to form a film having a film thickness of between 20 μm and 120 μm, and the formed optical film had a high warpage.
In addition, the optical film formed from the photosensitive resin composition (comparative example 2) in which the bisphenol fluorene oligomer (B) was replaced with the epoxy acrylic oligomer (B') had high warpage and insufficient transmittance to visible light and infrared rays.
In summary, when the photosensitive resin composition of the present invention contains the compound containing an ethylenic unsaturated group and a specific bisphenol fluorene oligomer and the weight ratio of the compound containing an ethylenic unsaturated group to the bisphenol fluorene oligomer is 0.50 to 0.95, the optical film formed by the photosensitive resin composition has low warpage and high transmittance, thereby improving the problem that the thick film causes warpage and insufficient transmittance of the substrate.
Although the present invention has been described with reference to the above embodiments, it should be understood that the invention is not limited thereto, but rather is capable of modification and variation without departing from the spirit and scope of the present invention.
Claims (12)
1. A photosensitive resin composition comprising:
a ethylenically unsaturated group-containing compound having two aromatic rings;
b bisphenol fluorene oligomer having two (meth) acryl groups; and
a photo-initiator of the formula C,
wherein the weight ratio of the compound containing ethylene unsaturated group A to the bisphenol fluorene oligomer B is 0.538-0.851,
the compound containing an ethylenically unsaturated group A comprises a compound represented by the formula (1),
in the formula (1), n1 and m1 are each independently integers of 0 to 20, and the sum of n1 and m1 is an integer of 1 to 20.
2. The photosensitive resin composition according to claim 1, further comprising an E solvent, wherein the E solvent is contained in an amount of 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 weight average molecular weight of the B bisphenol fluorene oligomer is 500 to 5000.
5. The photosensitive resin composition according to claim 1, wherein the viscosity of the photosensitive resin composition is 600 to 7000 mPa-s at 25 ℃.
6. A method for manufacturing an optical film includes
Applying the photosensitive resin composition according to any one of claims 1 to 5 to a substrate to form a coating film;
the coating film is subjected to an exposure step,
and performing a baking step on the exposed coating film to form an optical film on the substrate.
7. The method for producing an optical film according to claim 6, wherein the wavelength of the exposure step is 200 to 500nm.
8. The method for producing an optical film according to claim 6, wherein the baking step is carried out at a temperature of 130 ℃ to 280 ℃.
9. An optical film produced by the method for producing an optical film according to any one of claims 6 to 8.
10. The optical film according to claim 9, 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.
11. The optical film according to claim 9, 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.
12. The optical film of claim 9, wherein the optical film has a warp of less than 0.25mm relative to the substrate at a thickness of 20-120 μm.
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| TW201821522A (en) * | 2016-10-11 | 2018-06-16 | 日商迪愛生股份有限公司 | Active energy ray-curable resin composition for optical articles, cured product, and optical sheet |
| TW201823864A (en) * | 2016-12-30 | 2018-07-01 | 奇美實業股份有限公司 | Photosensitive resin composition and uses thereof |
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| US20150253464A1 (en) * | 2013-10-24 | 2015-09-10 | Chi Mei Corporation | Photosensitive resin composition and uses thereof |
| KR102268129B1 (en) * | 2017-10-16 | 2021-06-22 | 주식회사 엘지화학 | Unreactive fluoro compound and photopolymer composition comprising the same |
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| KR20100023126A (en) * | 2008-08-21 | 2010-03-04 | 에스에스씨피 주식회사 | Ultra-violet curable composition |
| JP2010204363A (en) * | 2009-03-03 | 2010-09-16 | Nippon Steel Chem Co Ltd | Photosensitive resin composition for black resist and color filter light-shielding film |
| JP2013238837A (en) * | 2011-11-21 | 2013-11-28 | Toyo Ink Sc Holdings Co Ltd | Photosensitive dry film, and protective film and touch-panel insulating film using the same |
| KR20160081747A (en) * | 2014-12-30 | 2016-07-08 | 코오롱인더스트리 주식회사 | Photosensitive resin composition for Dry Film Photoresist |
| TW201821522A (en) * | 2016-10-11 | 2018-06-16 | 日商迪愛生股份有限公司 | Active energy ray-curable resin composition for optical articles, cured product, and optical sheet |
| TW201823864A (en) * | 2016-12-30 | 2018-07-01 | 奇美實業股份有限公司 | Photosensitive resin composition and uses thereof |
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