CN112694557B - Photocurable resin, photocurable resin composition, and black matrix material - Google Patents
Photocurable resin, photocurable resin composition, and black matrix material Download PDFInfo
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- CN112694557B CN112694557B CN201911013541.7A CN201911013541A CN112694557B CN 112694557 B CN112694557 B CN 112694557B CN 201911013541 A CN201911013541 A CN 201911013541A CN 112694557 B CN112694557 B CN 112694557B
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- resin composition
- photocurable resin
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- 239000011347 resin Substances 0.000 title claims abstract description 95
- 229920005989 resin Polymers 0.000 title claims abstract description 95
- 239000011342 resin composition Substances 0.000 title claims abstract description 61
- 239000011159 matrix material Substances 0.000 title claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- 239000003513 alkali Substances 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000003999 initiator Substances 0.000 claims description 24
- 239000004925 Acrylic resin Substances 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 18
- 229920000178 Acrylic resin Polymers 0.000 claims description 17
- 239000003086 colorant Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000008064 anhydrides Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 150000008065 acid anhydrides Chemical group 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 22
- -1 methoxymethylene group Chemical group 0.000 description 22
- 239000000049 pigment Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000000016 photochemical curing Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 2
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- DIQMPQMYFZXDAX-UHFFFAOYSA-N Pentyl formate Chemical compound CCCCCOC=O DIQMPQMYFZXDAX-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 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
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N dimethyl monosulfide Natural products CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical compound COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 description 1
- OWSKJORLRSWYGK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) propanoate Chemical compound CCC(=O)OCCC(C)(C)OC OWSKJORLRSWYGK-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- VYMSWGOFSKMMCE-UHFFFAOYSA-N 10-butyl-2-chloroacridin-9-one Chemical compound ClC1=CC=C2N(CCCC)C3=CC=CC=C3C(=O)C2=C1 VYMSWGOFSKMMCE-UHFFFAOYSA-N 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- QIRUERQWPNHWRC-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(CC=2C=C3OCOC3=CC=2)=N1 QIRUERQWPNHWRC-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 1
- QRHHZFRCJDAUNA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 QRHHZFRCJDAUNA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- RQZUWSJHFBOFPI-UHFFFAOYSA-N 2-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COCC1CO1 RQZUWSJHFBOFPI-UHFFFAOYSA-N 0.000 description 1
- FVCHRIQAIOHAIC-UHFFFAOYSA-N 2-[1-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COC(C)COCC1CO1 FVCHRIQAIOHAIC-UHFFFAOYSA-N 0.000 description 1
- KQFHZFMPTSHGLV-UHFFFAOYSA-N 2-[1-[1-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxy]propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COC(C)COC(C)COCC1CO1 KQFHZFMPTSHGLV-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- FMVOPJLFZGSYOS-UHFFFAOYSA-N 2-[2-(2-ethoxypropoxy)propoxy]propan-1-ol Chemical compound CCOC(C)COC(C)COC(C)CO FMVOPJLFZGSYOS-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- VSRMIIBCXRHPCC-UHFFFAOYSA-N 2-[2-[2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxy]ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCCOCCOCC1CO1 VSRMIIBCXRHPCC-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SURWYRGVICLUBJ-UHFFFAOYSA-N 2-ethyl-9,10-dimethoxyanthracene Chemical compound C1=CC=CC2=C(OC)C3=CC(CC)=CC=C3C(OC)=C21 SURWYRGVICLUBJ-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-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
- LETDRANQSOEVCX-UHFFFAOYSA-N 2-methyl-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound CC1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 LETDRANQSOEVCX-UHFFFAOYSA-N 0.000 description 1
- YQIGLEFUZMIVHU-UHFFFAOYSA-N 2-methyl-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C(C)=C YQIGLEFUZMIVHU-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- MWDGNKGKLOBESZ-UHFFFAOYSA-N 2-oxooctanal Chemical compound CCCCCCC(=O)C=O MWDGNKGKLOBESZ-UHFFFAOYSA-N 0.000 description 1
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- C08F220/10—Esters
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- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
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- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
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- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
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Abstract
The invention provides a light-cured resin, a light-cured resin composition and a black matrix material. The light-cured resin has the following structure:
R1is C6～C20Cycloalkyl of (C)6～C20Any one of the aryl groups of (a); r2、R3、R4、R5Each independently is H, C1～C10Alkyl of (C)3～C20Cycloalkyl of, C6～C20Any one of the aryl groups of (a); r6Having a radical-R7‑Si‑(R8)n1(OR9)n2Shown structure, R7Is C1～C10Alkylene of (C)1～C15Any of the alkylene alkoxy groups of (1), each R8Each independently is C1～C10Alkyl of (C)1～C15Any of the alkoxy groups of (1), each R9Each independently is hydrogen, C1～C10Any of (a) alkyl groups. When the light-cured resin is used together with alkali-soluble resin, a film structure with high substrate adhesion, good alkali-resistant solubility and good heat resistance can be formed.
Description
Technical Field
The invention relates to the field of light-cured resin, in particular to light-cured resin and a light-cured resin composition black matrix material.
Background
In recent years, flat panel displays have been required to use a bright backlight as the display area has been enlarged. As the backlight becomes brighter, the requirements for the light shielding performance of the black matrix, the fineness of the development, and the like become higher and higher. In order to improve the light-shielding property and contrast of the black matrix, a method of increasing the pigment content is often employed. With the increase of the pigment content, the adhesion force of the black matrix to the substrate is weakened, and the alkali solubility, the heat resistance and the like are affected to different degrees. Japanese patent publication JP2006259716A discloses adding a difunctional reactive monomer to a photosensitive resin composition to increase the degree of crosslinking of the photosensitive resin composition upon exposure to light to form a black matrix having a high-definition pattern.
The polymer compound having a fluorene skeleton has excellent characteristics such as high heat resistance, high transparency, high refractive index, and low expansion coefficient, and for example, chinese patent with publication number CN100564349C and chinese patent application with publication number CN101965375A disclose: the fluorine-containing high molecular compound can solve the problem that the traditional light-cured resin composition cannot achieve high refractive index and heat resistance to a certain extent, but the adhesion, alkali-resistant solubility, solvent resistance and the like of a film layer formed by the obtained light-cured resin composition to a substrate cannot meet the requirements. Chinese patent application publication No. CN109343308A discloses a siloxane-modified acrylate composition, wherein the acid resistance of the coating film is significantly improved, but no clear description is provided for alkali solubility and the like. Chinese patent application publication No. CN103718107A discloses a silane-modified resin-containing composition which has a certain improvement in adhesion to a developed pattern, but has a certain deficiency in alkali solubility, heat resistance, and the like.
Disclosure of Invention
The invention mainly aims to provide a light-cured resin, a light-cured resin composition and a black matrix material, which are used for solving the problem that the light-cured resin in the prior art cannot simultaneously have alkali solubility and heat resistance when being applied.
In order to achieve the above object, according to one aspect of the present invention, there is provided a photocurable resin having a structure represented by structural formula I:
wherein R is1Is represented by C6～C20Cycloalkyl of, C6～C20Any one of the aryl groups of (a); r2、R3、R4、R5Are the same or different, and R2、R3、R4、R5Each independent representation H, C1～C10Alkyl of (C)3～C20Cycloalkyl of, C6～C20Any one of the aryl groups of (a); r6Having a radical-R7-Si-(R8)n1(OR9)n2Shown structure, R7Is represented by C1～C10Alkylene of (C)1～C15Any one of the alkylene alkoxy groups of (1), each R8Each independently represents C1～C10Alkyl of (C)1～C15Any one of the alkoxy groups of (1), each R9Each independently represents hydrogen or C1～C10Any one of the alkyl groups of (1), in R8Or R9When there are plural, each R8Identical or different, each R9Same or different, n1And n2Is a positive integer and n1+n23; x, y, z, n each independently represent an integer, and x and n are not 0.
Further, the above R1Is represented by C6～C12Cycloalkyl of, C6～C12Any one of aromatic groups.
Further, the above R2、R3、R4、R5Same, preferably R2、R3、R4、R5Is any one of H, methyl, isopropyl, cyclohexyl, phenyl and benzyl.
Further, the above R6In, R7Is represented by C1～C5Alkylene of (C)1～C10Any of the alkylene alkoxy groups of (1), preferably C1～C5Alkyl of (C)3～C5Any one of the alkylene alkoxy groups of (a); n is1Is 2, n2Is 1, each R8All represent C1～C5Alkyl of (C)1～C10Any one of alkoxy, R9Is represented by C1～C5Alkyl of (C)1～C10Any of the alkoxy groups of (1), preferably C1～C5Alkyl of (C)1～C5Any one of alkoxy groups.
Further, the weight average molecular weight of the light-cured resin is 5000-15000, and more preferably 6000-10000.
According to another aspect of the present invention, there is provided a photocurable resin composition comprising a photocurable acrylate-based resin, an alkali-soluble resin, a photopolymerizable monomer and an initiator, the photocurable acrylate-based resin being any one of the photocurable resins described above.
Further, the alkali-soluble resin has the following structural formula:
wherein A and B are substituents, n3Is any integer of 1 to 20.
Further, a is selected from any one of the following groups:
indicates possible attachment positions of acid anhydride;
further, the above B is selected from any one of the following groups:
indicates the possible attachment sites of the anhydride.
Further, the total mass part of the light-cured acrylate resin and the alkali-soluble resin is 10-50 parts by mass, preferably the total mass part of the light-cured acrylate resin and the alkali-soluble resin is 20-30 parts by mass, and the mass ratio of the light-cured acrylate resin to the alkali-soluble resin is 7: 10-8: 10; 1 to 30 parts by mass of a photopolymerizable monomer, more preferably 15 to 25 parts by mass; the photopolymerization initiator is 1 to 5 parts by mass, more preferably 1 to 3 parts by mass.
Further, the photo-curable resin composition further comprises a colorant, and the colorant is 30 to 60 parts by mass, preferably 40 to 50 parts by mass.
According to still another aspect of the present invention, there is provided a black matrix material comprising a photocurable resin composition, wherein the photocurable resin composition is any one of the photocurable resin compositions described above.
By applying the technical scheme of the invention, the photocuring resin with the structural formula I is characterized in that a silane group is used as a side chain group to be suspended on a polymer main chain, and when the photocuring resin is matched with alkali-soluble resin in the field for use, a film layer structure with high substrate adhesion, good alkali-resistant solubility and good heat resistance can be formed.
Detailed Description
It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict. The present invention will be described in detail with reference to examples.
As analyzed in the background of the present application, the photocurable resin of the prior art cannot simultaneously have alkali solubility and heat resistance when applied, and in order to solve the problem, the present application provides a photocurable resin, a photocurable resin composition, a photoresist and a black matrix material.
In one exemplary embodiment of the present application, there is provided a photocurable resin having a structure represented by structural formula I:
wherein R is1Is represented by C6～C20Cycloalkyl of (C)6～C20Any one of the aryl groups of (a); r2、R3、R4、R5Are the same or different, and R2、R3、R4、R5Each independent representation H, C1～C10Alkyl of (C)3～C20Cycloalkyl of, C6～C20Any one of the aryl groups of (a); r6Having a radical-R7-Si-(R8)n1(OR9)n2Shown structure, R7Is represented by C1～C10Alkylene of (C)1～C15Any one of the alkylene alkoxy groups of (1), each R8Each independently represents C1～C10Alkyl of (C)1～C15Any one of the alkoxy groups of (1), each R9Each independently represents hydrogen or C1～C10Any one of the alkyl groups of (1), in R8Or R9When there are plural, each R8Identical or different, each R9Same or different, n1And n2Is a positive integer and n1+n23; x, y, z, n each independently represent an integer, and x and n are not 0.
The photocuring resin with the structural formula I is characterized in that a silane group is suspended on a polymer main chain as a side chain group, and when the photocuring resin is matched with alkali-soluble resin in the field for use, a film layer structure with high substrate adhesion, good alkali-resistant solubility and good heat resistance can be formed.
In order to improve the hardness and heat resistance of the resin, the above R is preferable1Is represented by C6～C12Cycloalkyl of, C6～C12In the aromatic radicalAny of the above, cyclohexyl, phenyl or benzyl is more preferable. Compared with other monomers with large cyclic groups, the monomers containing the groups have the advantages that the raw materials are more easily available, and the hardness and the heat resistance can meet the requirements.
In order to improve the stability of the structural formula I and the efficiency of the synthesis, the above R is preferred2、R3、R4、R5Same, preferably more preferably R2、R3、R4、R5Is any one of H, methyl, isopropyl, cyclohexyl, phenyl and benzyl.
In order to improve the heat resistance and substrate adhesion of the resin and the efficiency of synthesis, the above R is preferably used6In, R7Is represented by C1～C5Alkylene of (C)1～C10Any of the alkylene alkoxy groups of (1), preferably C1～C5Alkyl of (C)3～C5Any of the above alkylene alkoxy groups, more preferably R7Represents a methylene group or a methoxymethylene group; n is1Is 2, n2Is 1, each R8All represent C1～C5Alkyl of (C)1～C10Any one of the alkoxy groups, preferably each R8All represent H, any one of methyl, ethyl, methoxy and ethoxy, R9Is represented by C1～C5Alkyl of (C)1～C10Any one of the alkoxy groups of (1), preferably C1～C5Alkyl of (C)1～C5Any one of alkoxy, more preferably R9Represents any one of H, methyl, ethyl, methoxy and ethoxy.
In one embodiment of the present application, in order to increase the curing rate of the photocurable resin, the weight average molecular weight of the photocurable resin is preferably 5000 to 15000, and more preferably 6000 to 10000.
In another exemplary embodiment of the present application, there is provided a photocurable resin composition including a photocurable acrylate-based resin, an alkali-soluble resin, a photopolymerizable monomer, an initiator, and a solvent, the photocurable acrylate-based resin being any one of the photocurable resins described above.
The photocuring resin with the structural formula I is characterized in that a silane group is suspended on a polymer main chain as a side chain group, and when the photocuring resin is matched with alkali-soluble resin in the field for use, a film layer structure with high substrate adhesion, good alkali-resistant solubility and good heat resistance can be formed.
Any alkali-soluble resin can be considered to be used in combination with the above-mentioned photocurable resin of the present application in the prior art, and it is preferable that the alkali-soluble resin contains a fluorene group, and it is further preferable that the alkali-soluble resin has the following structural formula
Wherein A and B are substituents, n3Is any integer of 1 to 20.
Compared with the carboxylic acid group content of the conventional similar alkali-soluble resin in the prior art, the carboxylic acid group content of the alkali-soluble resin is less, the content of active groups such as side chain alcoholic hydroxyl groups is increased, the acid value of the photosensitive resin is further reduced, the reaction activity and the curing rate are improved, and the photocuring performance, the adhesion to a substrate, the alkali-resistant solvent resistance and the solvent resistance of the composition are further improved.
The substituent group represented by a in the above structural formula may be theoretically any chemically acceptable group, and in order to further optimize the advantages of the photosensitive resin, it is preferable that a is selected from any one of the following groups:
indicates the possible attachment sites of the anhydride.
The substituent group represented by B in the structural formula may be theoretically any chemically acceptable group, and in order to stabilize the performance of the photosensitive resin, it is preferable that B is selected from any one of the following groups:
indicates the possible attachment sites of the anhydride.
In order to fully exert the advantages of the resins, the total mass part of the light-cured acrylic resin and the alkali-soluble resin is 10-50 parts, preferably the total mass part of the light-cured acrylic resin and the alkali-soluble resin is 20-30 parts, and the mass ratio of the light-cured acrylic resin to the alkali-soluble resin is 7: 10-8: 10.
in one embodiment, the photopolymerizable monomer is 1 to 30 parts by mass, and more preferably 15 to 25 parts by mass. The photopolymerizable monomer used in the photocurable resin composition is used to improve the properties of the photocurable resin composition, such as photosensitivity, mechanical strength, crosslinkability, and chemical resistance. As the polymerizable monomer, any one or a combination of several kinds of compounds may be selected as necessary as long as the compound has one or more unsaturated bonds in the molecule. Illustrative examples of the photopolymerizable monomers selected in the present invention include: (meth) acrylic acid adducts of epoxy compounds such as propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, tetrapropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, sorbitol triglycidyl ether, and glycerol triglycidyl ether; unsaturated organic acids such as maleic acid and anhydrides thereof; acrylamides such as N-methylacrylamide, N-ethylacrylamide, N-isopropylacrylamide, N-methylolacrylamide, N-methylacrylamide, N-ethylmethacrylamide, N-isopropylmethacrylamide, N-methylolmethacrylamide, N-dimethylacrylamide, N-diethylacrylamide, N-dimethylmethacrylamide, and N, N-diethylmethacrylamide; polyethylene glycol di (meth) acrylate (the number of ethylene groups is 2 to 14); trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane ethoxytri (meth) acrylate, trimethylolpropane propoxyttri (meth) acrylate, tetramethylolmethane tri (meth) acrylate, tetramethylolmethane tetra (meth) acrylate, polypropylene glycol di (meth) acrylate (propylene number is 2 to 14); dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol a polyoxyethylene di (meth) acrylate, bisphenol a ethylenedioxy di (meth) acrylate, bisphenol a oxyethylene di (meth) acrylate, esters of polycarboxylic acids (such as phthalic anhydride) with compounds having hydroxyl groups and ethylenically unsaturated groups (such as β -hydroxyethyl (meth) acrylate), alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, etc.; styrenes such as ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, styrene, and hydroxystyrene; n-vinylpyrrolidone, N-vinylformamide, N-vinylacetamide, N-vinylimidazole, etc.; the above-listed substances may be used alone or in combination of two or more.
In one embodiment, the photopolymerization initiator is preferably 1 to 5 parts by mass, and more preferably 1 to 3 parts by mass. The initiator in the photocurable resin composition is mixed in a state of being dissolved or dispersed in a solvent. The initiator used in the present invention is not particularly limited, and may be selected from one or a combination of more of benzophenone-based initiators, triazine-based initiators, dialkoxybenzophenone-based initiators, α -hydroxyalkylphenone-based initiators, α -aminoalkylphenone-based initiators, acylphosphine oxide initiators, benzophenone-based initiators, benzoin-based initiators, benzil-based initiators, heterocyclic arone-based initiators, and oxime ester-based photoinitiators. Oxime ester initiators are particularly preferred. An exemplary list is: benzophenone, 4-phenylbenzophenone, 4-benzoyl-4' -methyldiphenylsulfide, diethoxyacetophenone, 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6-piperonyl-1, 3, 5-triazine, benzoin methyl ether, benzoin isobutyl ether, 2-ethyl-9, 10-dimethoxyanthracene, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, 9, 10-phenanthrenequinone, o-ethoxycarbonyl-a-oxyimino-1-phenylpropan-one, 1, 2-octanedione, methyl ethyl acetate, or ethyl acetate, or ethyl acetate, or a-2-acetate, or a salt, 1- (4-phenylthio) phenyl-2 (O-benzoyloxime), 1- (9-ethyl) -6- (2-methylbenzoyl) carbazol-3 yl-1- (O-acetyloxime), OXE-01, NCI-831, 2,4, 5-triarylimidazole dimer, 4 '-bisdiethylaminobenzophenone, 4' -dichlorobenzophenone, 2-methylthioxanthone, 2-isopropylthioxanthone, dibenzosuberone, trichloroacetophenone, pentyl-4-dimethylaminobenzoate, 9-phenylacridine, 1, 7-bis (9-acridinyl) heptane, 1, 3-bis (9-acridinyl) propane, 2-methyl-4, 6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) vinyl ] -4, 5-bis (trichloromethyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) vinyl ] -4, 6-bis (trichloromethyl) -s-triazine, 2, 4-bis (trichloromethyl) -6- (2-bromo-4-methoxy) phenyl-s-triazine, 2, 4-bis (trichloromethyl) -6- (3-bromo-4-methoxy) styrylphenyl-s-triazine, 2, 4-bis (trichloromethyl) -6- (2-bromo-4-methoxy) styrylphenyl-s-triazine, 4-benzoyl-4' -methyl dimethyl sulfide, 4-dimethyl ethyl aminobenzoate, 4-dimethyl methyl aminobenzoate, benzyl-beta-methoxyethyl acetal, benzyl dimethyl ketal, 1-phenyl-1, 2-propanedione-2 (o-ethoxycarbonyl) oxime, and the like.
In the case where the photocurable resin composition of the present invention is used for applications such as optical filter production, a solvent for dispersion is required. As the common solvent, there can be selected (poly) alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol n-propyl ether, ethylene glycol n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, etc.; aromatic hydrocarbons, for example: toluene, xylene, trimethylbenzene, etc.; amide compounds, such as: n-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, and the like; carboxylic acid ester compounds, for example: ethyl 2-oxobutyrate, methyl acetoacetate, ethyl acetate, n-propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl acetone, methyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl glycolate, methyl 2-hydroxy-3-methylbutyrate, 3-methyl-3-methoxybutylacetate, isopropyl acetate, butyl acetate, isobutyl acetate, n-pentyl formate, isoamyl acetate, butyl propionate, ethyl butyrate, butyl propionate, ethyl, 3-methyl-3-methoxybutyl propionate and the like; solvents of the same type, for example: methyl ethyl ketone, cyclohexanone, heptanone, 3-heptanone, and the like; cyclic ether compounds such as tetrahydrofuran, pyran, and the like; cyclic ester compounds such as gamma-butyrolactone, etc. The organic solvent may be used alone or in combination of two or more, wherein the solvents such as propylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether, diethylene glycol methyl ethyl ether and the like have good solubility for the photosensitive resin composition of the present invention; further preferred solvents are propylene glycol monomethyl ether acetate, diethylene glycol methyl ethyl ether. The amount of the solvent added is preferably such that the solid content of the photocurable resin composition is 10-50 wt%, more preferably 15-40 wt%.
The above-mentioned photocurable resin composition may further optionally contain a colorant commonly used in the art according to the application requirements of the product, and a color filter may be well formed by adding the colorant.
Any organic pigment, inorganic pigment, which is generally used in the art may be selectively used as the colorant of the present application. These include water-soluble pigments, water-insoluble azo pigments, phthalocyanine pigments, acridone pigments, isoindoline pigments, benzanthrone pigments, indanthrone pigments, diketopyrrolopyrrole pigments, and the like. The pigments can be used singly or after being mixed, and are determined according to specific requirements of products.
Further preferred are organic raw materials, and specific pigments are exemplified below, but not limited to, the following pigments. Compounds with a color index (The Society of dyeing and Colourists) (C.I.) number are listed as follows:
c.i. pigment black 1 and 7, etc.
When the colorant is used as a light-shading agent, a black pigment is preferably used, and examples of the black pigment include carbon black, titanium black, metal oxides such as copper, iron, and manganese, complex oxides, metal sulfides, metal sulfates, and metal carbonates. Among them, carbon black having a high light-shielding property is preferable. The content of the colorant may be determined as appropriate depending on the use of the photosensitive resin composition, and is preferably 30 to 60 parts by mass, and more preferably 40 to 50 parts by mass. In order to uniformly disperse the colorant in the photocurable resin composition, a dispersant may also be used. As such a dispersant, a polyethyleneimine, a urethane resin-based, or an acrylic resin-based polymer dispersant, particularly an oleic acid acrylic resin-based dispersant, is preferably used.
When the photocurable resin composition contains the above photocurable acrylate resin, alkali-soluble resin, photopolymerizable monomer, initiator, colorant and solvent, the total parts by mass of the photocurable resin composition is 100 parts by mass: the total mass part of the light-cured acrylic resin and the alkali-soluble resin is 10-50 parts by mass, preferably 20-30 parts by mass; 20-60 parts by mass of a colorant, preferably 30-40 parts by mass; 1 to 30 parts by mass of a photopolymerizable monomer, preferably 15 to 25 parts by mass; 1 to 5 parts by mass of a photopolymerization initiator, preferably 1 to 3 parts by mass; the solvent is 10 to 50 parts by mass, preferably 15 to 40 parts by mass.
In another preferred embodiment of the present invention, the above-mentioned photocurable resin composition may contain additives such as, but not limited to, fillers, curing agents, leveling agents, adhesion promoters, antioxidants, ultraviolet absorbers, and the like.
Among them, the curing agent is used to improve deep curability and mechanical strength. As the curing agent, specifically, an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, an oxetane compound and the like can be used, but not limited to these compounds. The leveling agent may be a commercially available surfactant, and specifically, may include silicone surfactants, ester surfactants, ionic surfactants, nonionic surfactants, amphoteric surfactants, and the like, and these surfactants may be used alone or in combination of two or more. The adhesion promoter may be a silane compound, and specific examples thereof include: vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -30-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, etc. The adhesion promoters may be used alone or in combination of two or more. Specific examples of the antioxidant include: 4,4 '-butylidenebis (6-tert-butyl-3-methylphenol), 2, 6-di-tert-butyl-4-methylphenol, 2,3' -thiobis (4-methyl-6-tert-butylphenol), p-methoxyphenol and the like. The ultraviolet absorbent can be 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzotriazole, alkoxybenzophenone, etc.
In another exemplary embodiment of the present application, there is provided a black matrix material including a photocurable resin composition, the photocurable resin composition being any one of the photocurable resin compositions described above. The photo-curing resin composition has the advantages of strong adhesion, alkali solubility resistance and high temperature resistance, so that the adhesion of the formed black matrix has the advantages.
The above-mentioned photocurable resin is synthesized by reacting a silane coupling agent having an active substituent group such as an epoxy group or a hydroxyl group with an acrylic copolymer resin having a carboxyl group in the presence of a catalyst to obtain an organosilane-modified acrylic resin, i.e., a photocurable resin of the present application. The following exemplifies a method for synthesizing the photocurable resin.
Synthesis example 1
100g of Propylene Glycol Methyl Ether Acetate (PGMEA) is added into a 500ml four-neck flask provided with a stirring device, a condenser pipe, a constant pressure dropping funnel, a thermometer and a nitrogen inlet, nitrogen is filled, the mixture is heated to 70 ℃ under the stirring condition, a monomer mixture (the formula is shown in table 1) and an initiator (azodiisoheptonitrile) solution are respectively dripped, the dripping time is controlled to be 2 hours, after the dripping is finished, the temperature is kept for 4 hours at the temperature, and the temperature is reduced after the Mw of a measuring system meets the requirement, so that the acrylic resin is obtained. According to different monomer combinations, acrylic resins 1-5 and comparative resins were prepared respectively, and the specific formulations are shown in table 1.
TABLE 1
Synthesis example 2
Adding a certain amount of the acrylic resin 1 into a 500ml reaction four-mouth bottle, heating to 110 ℃, adding 0.5% (relative to the mass of the resin) of tetrabutylammonium bromide and silane coupling agent 3- (2, 3-epoxypropoxy) propyltriethoxysilane (containing epoxy groups) after the temperature of the system is stable, carrying out heat preservation reaction at 110 ℃ for 2h, starting to test the epoxy equivalent of the system, stopping the reaction when the epoxy equivalent is more than 25000g/mol, cooling, discharging and sealing to obtain the organosilane modified acrylic resin 1, namely the modified resin 1.
By adopting the method, the acrylic resins 2 to 5 are modified by using the silane coupling agent to prepare the silane-modified acrylic resins 2 to 15, and the specific silane coupling agent and the modified resin are shown in the following tables 2 to 4.
Synthesis of comparative example 1 (comparative resin 1)
Adding a certain amount of the comparative resin prepolymer into a 500ml reaction four-mouth bottle, heating to 110 ℃, adding 0.5% (relative to the mass of the resin) of tetrabutylammonium bromide and Glycidyl Methacrylate (GMA) after the temperature of the system is stable, carrying out heat preservation reaction at 110 ℃ for 2h, starting to test the epoxy equivalent of the system, stopping the reaction when the epoxy equivalent is more than 25000g/mol, cooling, discharging and sealing to obtain the comparative resin 1.
TABLE 2
TABLE 3
TABLE 4
Evaluation of Photocurable resin composition
1. Preparation of light-curable resin composition for simple evaluation
Exemplary photocurable resin compositions were formulated and evaluated for the application properties of the organosilane-modified resins given in the examples of the present invention. The modified resins prepared in the above examples are preferably subjected to test comparison. Referring to the formulations shown in examples 1 to 15 and comparative examples 1 to 2 in Table 5, the raw materials were uniformly mixed in the following proportions to form a photocurable resin composition.
Wherein the light-cured resin is mixed with a part of the solvent and then mixed with other components.
TABLE 5
Note: the alkali-soluble resin II selected herein has the structural formula shown in the following figure:
the photocurable resin compositions of examples 16 to 20 were prepared according to the mass ratios in table 5 by selecting different ratios of the modified resin 1 to the alkali-soluble resin II, and the corresponding photopolymerizable monomers, initiators, colorants and solvents were the same as in example 1 and compared, and the specific examples are shown in table 6.
TABLE 6
2. Evaluation of application Properties of photo-curable resin composition
The photocurable resin compositions of examples 1 to 20 and comparative examples 1 and 2 were applied onto a glass substrate (100 mm. times.100 mm) by means of a spin coater, and prebaked at 90 ℃ for 90 seconds to form a coating film having a thickness of 1.0. mu.m. Then, the exposure gap was set to 50 μm using a mirror projection alignment exposure apparatus, and isolated exposure was performed using a negative mask having a line pattern of 20 μm. The exposure intensity was set at 20, 40, 60, 120mJ/cm24 grades. The exposed sample coating film is respectively developed in 0.04 mass percent KOH aqueous solution at 26 ℃ for 40s, 60s and 80s, then is baked at 230 ℃ for 30 minutes to form a linear pattern, the pattern characteristics and the film forming residual rate are tested, and the performances of alkali solubility, solvent resistance and the like are detected.
Similarly, the coating film was irradiated with ultraviolet rays at an exposure gap of 50 μm through a negative mask having a linear pattern of 2, 5, 10, or 20 μm. The exposure amount was set to 20mJ/cm2. The exposed coating film was developed in a 0.04 mass% KOH aqueous solution at 26 ℃, and then post-baked at 230 ℃ for 30min to form a line pattern. The formed pattern was observed with an optical microscope to evaluate the linearity of the pattern andand (4) adhesion. The specific evaluation is shown in Table 7 below. The application effects of the photoresist resin compositions containing the modified resin 1 and the alkali-soluble resin II in different proportions were also evaluated, and the specific evaluation results are shown in Table 8.
Evaluation criteria:
pattern linearity:
o: the edge of the pattern line has no sawtooth;
and (delta): the edges of the pattern lines are jagged.
Adhesion of pattern to substrate:
no peeling from the substrate, forming a linear pattern;
although a linear pattern is formed, pattern defects occur in Δ;
the gamma rays are peeled off from the substrate without forming a linear pattern.
TABLE 7
TABLE 8
The above results of the measurements showed that the concentrations of the compounds in examples 2, 5, 9,10, 13, 14 and the like were 40mJ/cm2Has shown better linearity at 60mJ/cm when exposed to light2The examples showed good linearity at the exposure, while the comparative examples showed poor linearity and had edge jaggies. The adhesion test shows that the 2 μm line pattern, examples 1 to 15 all showed a certain adhesion; while the adhesion of the pattern having a line width of 5 μm to 10 μm was remarkably good, the pattern of comparative example was peeled off in the line pattern of 2 μm, and the line pattern of 10 μm was also remarkably defective.
The linearity comparison of examples 16 to 20 shows that the 40mJ exposure energy condition is small, the linearity of example 18 is good, and the linearity of examples 16, 17, 19 and 20 is slightly insufficient; in comparison, the adhesion of the line pattern of 5 μm, examples 17, 18 and 19 showed better adhesion, while the adhesion of examples 16 and 20 was significantly lower. Therefore, a comprehensive comparison shows that the two resin ratios in example 18 are relatively suitable ratios. Other examples used this ratio for application performance testing.
Evaluation of Heat resistance and alkali solubility:
the coating film was irradiated with ultraviolet rays with an exposure gap of 50 μm through a negative mask having a linear pattern of 2, 5, 10, or 20 μm. The exposure amount was set to 20mJ/cm2. The exposed coating film was developed in a 0.04 mass% KOH aqueous solution at 26 ℃, and then post-baked at 230 ℃ for 30min to form a line pattern. The formed pattern was observed with an optical microscope, and heat resistance (contact angle between the pattern edge and the substrate) and alkali solubility were evaluated, and the evaluation was made from the result of the residual film rate measurement. The specific evaluation is shown in Table 9 below. In addition, the photocurable resin compositions containing the modified resin 1 and the alkali-soluble resin II in different proportions are compared, a better resin ratio is selected, and specific comparison results are shown in Table 10.
The evaluation criteria are as follows
Alkali solubility
The residual film rate is more than or equal to 95 percent
The film residue rate is more than or equal to 90 percent and is more than 95 percent
The gamma residual film rate is less than 90%
Heat resistance
Contact angle between pattern edge and substrate > 45 °
The contact angle between the edge of the delta pattern and the substrate is 40-45 DEG
The edge of the gamma pattern has a contact angle with the substrate of less than 40 °
TABLE 9
Watch 10
From the above test results, the photocurable resin compositions of examples 1-15 all have better alkali-resistant solubility; after post-baking at 230 ℃, the contact angles between the edges of the obtained patterns and the substrate are all larger than 45 degrees, the heat resistance is better, the contact angles of the comparative examples are all smaller than 40 degrees, and the heat resistance is relatively poorer.
In addition, as can be seen from the comparison of the photocurable resin compositions containing the modified resin 1 and the alkali-soluble resin II in different proportions, examples 17, 18, 19, etc. all have better alkali-resistant solubility and heat resistance, and particularly, example 18 has excellent alkali-resistant solubility and heat resistance, so that the proportion of the modified resin and the alkali-soluble resin II corresponding to example 18 is a relatively better proportion condition, and other comparative examples are evaluated for the preparation and application of the composition with reference to the proportion.
In conclusion, the organosilane-modified photocurable resin and the composition thereof provided by the invention have excellent application performance, better heat resistance, better linearity and adhesion and wide application prospect.
From the above description, the above-described embodiments of the present invention achieve the following technical effects:
in the application, the light-cured resin composition prepared by using the photosensitive resin with the specific structural formula I in combination with the alkali-soluble resin has the advantages of good developing linearity, good adhesion to a substrate, good heat resistance after baking and good alkali-resistant solubility.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (15)
1. A light-cured resin composition comprises a light-cured acrylic resin, an alkali-soluble resin, a photopolymerizable monomer and an initiator, and is characterized in that the total mass of the light-cured acrylic resin and the alkali-soluble resin is 10-50 parts by mass, and the mass ratio of the light-cured acrylic resin to the alkali-soluble resin is 7: 10-8: 10, the light-cured acrylic resin is a light-cured resin, and the light-cured resin has a structure shown in a structural formula I:
wherein R is1Is represented by C6～C20Cycloalkyl of, C6～C20Any one of the aryl groups of (a);
R2、R3、R4、R5are the same or different, and R2、R3、R4、R5Each independent representation H, C1～C10Alkyl of (C)3～C20Cycloalkyl of, C6～C20Any one of the aryl groups of (a);
R6having a radical-R7-Si-(R8)n1(OR9)n2Shown structure, R7Is represented by C1～C15Any one of the alkylene alkoxy groups of (1), each R8Each independently represents C1～C10Alkyl of (C)1～C15Any one of the alkoxy groups of (1), each R9Each independently represents hydrogen or C1～C10Any one of the alkyl groups of (1), in R8Or R9When there are plural, each R8Identical or different, each R9Same or different, n1And n2Is a positive integer andn1+n2＝3；
x, y, z, n each independently represent an integer, and x and n are not 0,
the alkali soluble resin has the following structural formula
Wherein A and B are substituents, n3Is an integer of 1 to 20,
a is selected from any one of the following groups:
indicates the attachment position of the acid anhydride;
the B is selected from any one of the following groups:
denotes the attachment position of the anhydride.
2. The photocurable resin composition according to claim 1, wherein the photopolymerizable monomer is 1 to 30 parts by mass; the initiator is 1-5 parts by mass.
3. The photocurable resin composition according to claim 2, wherein the photopolymerizable monomer is 15 to 25 parts by mass.
4. The photocurable resin composition according to claim 2, wherein the initiator is 1-3 parts by mass.
5. The photocurable resin composition according to claim 1, wherein said R is1Is represented by C6～C12Cycloalkyl of, C6～C12Any one of aromatic groups.
6. The photocurable resin composition according to claim 1, wherein said R is2The R is3The R is4The R is5The same is true.
7. The photocurable resin composition according to claim 6, wherein R is2The R is3The R is4The R is5Is any one of H, methyl, isopropyl, cyclohexyl, phenyl and benzyl.
8. The photocurable resin composition according to claim 1, wherein said R is6In (1), the R7Is represented by C1～C10Any one of the alkylene alkoxy groups of (1), n1Is 2, n2Is 1, each of said R8All represent C1～C5Alkyl of (C)1～C10Any one of alkoxy, said R9Is represented by C1～C5Alkyl of (C)1～C10Any one of the alkoxy groups of (1).
9. The photocurable resin composition according to claim 8, wherein R is7Is represented by C3～C5Any one of the alkylene alkoxy groups of (a).
10. The photocurable resin composition according to claim 8, wherein R is9Is C1～C5Alkyl of (C)1～C5Any of alkoxy groupsThe method is as follows.
11. The photocurable resin composition according to claim 1, wherein the weight average molecular weight of the photocurable resin is 5000-15000.
12. The photocurable resin composition of claim 11, wherein the weight average molecular weight of the photocurable resin is 6000-10000.
13. The photocurable resin composition according to any one of claims 2-4, further comprising a colorant in an amount of 30-60 parts by mass.
14. The photocurable resin composition according to claim 13, wherein the colorant is 40 to 50 parts by mass.
15. A black matrix material comprising a photocurable resin composition, wherein the photocurable resin composition is the photocurable resin composition according to any one of claims 1 to 14.
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