CN116867822A - Alkali-soluble resin, photosensitive resin composition, cured product, and image display device - Google Patents
Alkali-soluble resin, photosensitive resin composition, cured product, and image display device Download PDFInfo
- Publication number
- CN116867822A CN116867822A CN202280013436.7A CN202280013436A CN116867822A CN 116867822 A CN116867822 A CN 116867822A CN 202280013436 A CN202280013436 A CN 202280013436A CN 116867822 A CN116867822 A CN 116867822A
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- China
- Prior art keywords
- group
- carbon atoms
- alkali
- soluble resin
- organic group
- Prior art date
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- 229920005989 resin Polymers 0.000 title claims abstract description 106
- 239000011347 resin Substances 0.000 title claims abstract description 106
- 239000011342 resin composition Substances 0.000 title claims abstract description 46
- 125000000962 organic group Chemical group 0.000 claims abstract description 91
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 79
- 125000005647 linker group Chemical group 0.000 claims abstract description 42
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 52
- -1 acryloyloxy, methacryloyloxy Chemical group 0.000 claims description 42
- 239000000463 material Substances 0.000 claims description 28
- 125000006850 spacer group Chemical group 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 150000001721 carbon Chemical group 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 19
- 239000002243 precursor Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 239000011229 interlayer Substances 0.000 claims description 4
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- 230000001681 protective effect Effects 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000011161 development Methods 0.000 abstract description 27
- 230000008719 thickening Effects 0.000 abstract description 5
- 239000010408 film Substances 0.000 description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- 239000000243 solution Substances 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 23
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 18
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- 239000011521 glass Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 125000004430 oxygen atom Chemical group O* 0.000 description 9
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- 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 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
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- 239000002904 solvent Substances 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 239000007864 aqueous solution Substances 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
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- 239000007983 Tris buffer Substances 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 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
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
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- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
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- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 description 1
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002998 adhesive polymer Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 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
- YSRMRWIQPVDQBV-UHFFFAOYSA-N bis(prop-2-enoxy)phosphorylbenzene Chemical compound C=CCOP(=O)(OCC=C)C1=CC=CC=C1 YSRMRWIQPVDQBV-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 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
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- NWAHZAIDMVNENC-UHFFFAOYSA-N octahydro-1h-4,7-methanoinden-5-yl methacrylate Chemical compound C12CCCC2C2CC(OC(=O)C(=C)C)C1C2 NWAHZAIDMVNENC-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C08F120/00—Homopolymers 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
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F120/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- 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
- C08F120/00—Homopolymers 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
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/12—Polymers provided for in subclasses C08C or C08F
- C08F290/126—Polymers of unsaturated carboxylic acids or derivatives thereof
-
- 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- 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
-
- 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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Chemical & Material Sciences (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Crystal (AREA)
Abstract
The present invention aims to provide an alkali-soluble resin capable of forming a cured film excellent in development adhesion and resolution even in the case of thickening, and a photosensitive resin composition containing the alkali-soluble resin, and also to provide a photosensitive resin composition which can be developed in a short time even when a weakly alkaline developer is used, in addition to the above-mentioned characteristics. The alkali-soluble resin of the present invention comprises one or more kinds of repeating structural units X represented by the following general formula (1); in the formula (1), R 1 Is hydrogen or methyl, R 2 Is a linking group having 1 or more carbon atoms, R 3 Is an organic group represented by the following general formula (2) bonded to a carbon atom of the linking group, R 4 Is a hydroxyl group bonded to a carbon atom of the linking groupA radical or an organic radical; in the formula (2), R 5 Is an organic group having 3 to 8 carbon atoms as a parent or an organic group having 2 to 7 carbon atoms as a parent and having a carboxyl group;
Description
Technical Field
The invention relates to an alkali-soluble resin, a photosensitive resin composition, a cured product and an image display device.
Background
In a liquid crystal display element, a Photo-Spacer or a Photo Spacer, also called "gap control material", "Photo-resist Spacer", or the like, is used to maintain the thickness of a liquid crystal layer sandwiched between a color filter side substrate and a Thin Film Transistor (TFT) side substrate.
The photolithographic spacers are generally formed by the following method: the photosensitive resin composition is applied to a substrate, and after drying, is exposed to light through a photomask having a specific fine pattern and developed.
In recent years, with the higher functionality of image display devices such as liquid crystal display devices (for example, 3D stereoscopic vision, view angle expansion, etc.), the thickness of photolithographic spacers has been required to be thicker (10 μm or more).
For example, patent document 1 aims to provide a negative photosensitive resin composition capable of forming a fine photolithographic spacer excellent in development adhesion and resolution and good in shape even when thick film processing with a film thickness of 10 μm or more is performed, and proposes a negative photosensitive resin composition comprising (a) an alkali-soluble resin, (B) a photo radical polymerization initiator, and (C) a photo polymerizable monomer comprising (C-1) a photo polymerizable monomer having an isocyanuric acid skeleton and (C-2) a photo polymerizable monomer having a fluorene skeleton.
Further, an object of patent document 2 is to provide a photosensitive resin composition which can form a gap of 10 μm or more, has good adhesion to a substrate, and can ensure transparency after exposure, and in which a photosensitive resin composition is proposed which is used as a spacer forming material, and contains the following components: the adhesive composition comprises (A) an adhesive polymer, (B) a photopolymerizable compound, (C) a photopolymerization initiator, and (D) a mercapto-containing hydrogen donor, wherein the (B) a photopolymerizable compound comprises a photopolymerizable compound having an ethylenically unsaturated group and an isocyanuric acid ring structure.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2019-124929
Patent document 2: international publication No. 2013/115262
Disclosure of Invention
Technical problem to be solved
However, the photosensitive resin composition described in patent document 1 or 2 has room for improvement in development adhesion and resolution when the photolithographic spacer is thickened. Further, although there is a need for a photosensitive resin composition that can be developed using a relatively dilute aqueous solution that is weakly alkaline from an environmental point of view, there is a concern that the photosensitive resin composition described in patent document 1 or 2 may have a problem in that the development time becomes long and productivity is lowered when developed using a weakly alkaline aqueous solution.
The purpose of the present invention is to provide an alkali-soluble resin capable of forming a cured film excellent in development adhesion and resolution even when the film is thickened, and a photosensitive resin composition containing the alkali-soluble resin. Further, an object of the present invention is to provide a photosensitive resin composition which can be developed in a short time even when a weakly alkaline developer is used, in addition to the above-mentioned characteristics. Further, the present invention also provides a cured product obtained from the photosensitive resin composition and an image display device including the cured product.
Technical means for solving the problems
The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that the above-mentioned object can be achieved by using the following alkali-soluble resin and a photosensitive resin composition containing the alkali-soluble resin, and have completed the present invention.
The present invention relates to an alkali-soluble resin (hereinafter also referred to as "alkali-soluble resin A") comprising one or more kinds of repeating structural units X represented by the following general formula (1),
in the formula (1), R 1 Is hydrogen or methyl, R 2 Is a linking group having 1 or more carbon atoms, R 3 Is an organic group represented by the following general formula (2) bonded to a carbon atom of the linking group, R 4 Is a hydroxyl or organic group bonded to a carbon atom of the linking group;
in the formula (2), R 5 Is an organic group having 3 to 8 carbon atoms as a parent or an organic group having 2 to 7 carbon atoms as a parent and having a carboxyl group.
The present invention also relates to an alkali-soluble resin (hereinafter also referred to as "alkali-soluble resin B") comprising a repeating structural unit X 'represented by the following general formula (1'), but not comprising a repeating structural unit having a branched side chain having 2 to 3 terminals each ending with a radical polymerizable substituent.
In the formula (1'), R 1 Is hydrogen or methyl, R 2 Is a linking group having 1 or more carbon atoms, R 3 'is an organic group represented by the following general formula (2') bonded to a carbon atom of the linking group, R 4 Is a hydroxyl or organic group bonded to a carbon atom of the linking group;
in the formula (2'), R 5 ' is a hydrocarbon group having 2 to 7 carbon atoms as a precursor, an organic group having 3 to 8 carbon atoms as a precursor and containing a hetero atom, or an organic group having 2 to 7 carbon atoms as a precursor and having a carboxyl group.
In the alkali-soluble resin A or B, the R is preferably 2 The linking group of (a) is a hydrocarbon group having 1 to 10 carbon atoms as a precursor or an organic group having 1 to 10 carbon atoms as a precursor and containing a hetero atom.
In the alkali-soluble resin A or B, the R is preferably 4 The organic group of (a) is an organic group containing one or more functional groups selected from the group consisting of acryloyloxy, methacryloyloxy, acyloxy, amidooxy, alkoxy, aryloxy, amino, and nitrogen-containing heterocycle.
In addition, in the alkali-soluble resin A or B, the R is preferably 2 Is a hydrocarbon group having 1 to 7 carbon atoms as a parent or an organic group having 1 to 7 carbon atoms and containing a hetero atom as a parent, and
the R is 4 Is with said R 2 Hydroxyl, acryloxy or methacryloxy groups bonded to carbon atoms of the linking group of (c).
In addition, in the alkali-soluble resin A or B, R is preferably the same as R 2 The linking group of (a) is a hydrocarbon group having 1 to 7 carbon atoms as a parent or an organic group having 1 to 7 carbon atoms as a parent and containing a hetero atom,
the R is 5 Or said R 5 ' is an organic group represented by the following formula (3), and
the R is 4 Is with said R 2 Hydroxyl, acryloyloxy, methacryloyloxy bonded to a carbon atom of the linking group of (a) or an organic group represented by the following general formula (4).
In the formula (3), R 6 R is R 7 Respectively are provided withIndependently represents a hydrocarbon group of 1 to 6 carbon atoms of the parent, R 6 R is R 7 The total carbon number of the parent body of the catalyst is 3-8;
in the formula (4), R 8 Is hydrogen or methyl, R 9 Is a hydrocarbon group having 1 to 5 carbon atoms as a parent or an organic group having 1 to 5 carbon atoms as a parent and containing a hetero atom.
In the alkali-soluble resin a or B, the content of the repeating structural unit X or X' is preferably 5 to 50 mol% in all the repeating structural units.
The alkali-soluble resin A or B preferably has an acid value of 20mgKOH/g to 120mgKOH/g.
The alkali-soluble resin A or B preferably has a weight average molecular weight of 5000 to 40000.
The photosensitive resin composition of the present invention comprises at least the alkali-soluble resin A and/or B, a polymerizable monomer, and a photopolymerization initiator.
The cured product of the present invention is obtained from the photosensitive resin composition.
The cured product is preferably a photolithographic spacer, a spacer material, a lens material, an interlayer insulating film material, a protective film material, an optical waveguide material, or a planarizing film material.
The present invention also relates to an image display device comprising the cured product.
Advantageous effects
The alkali-soluble resin A or B of the present invention is characterized by having the following structure: comprises one or more repeating structural units X or X ' represented by the general formula (1) or (1 '), wherein the length of a side chain in the repeating structural units X or X ' is a length of a certain length or more, and the terminal of the side chain has a carboxyl group. The alkali-soluble resin a or B of the present invention has such a characteristic structure, and thus a cured film excellent in development adhesion and resolution can be obtained even in the case of thickening. In addition, the alkali-soluble resin A or B of the present invention has a group R bonded to the linking group 2 Hydroxyl group of carbon atom of (2)Or organic groups, and may thus in turn have properties derived from these groups. In addition, since the photosensitive resin composition containing the alkali-soluble resin a and/or B of the present invention can be developed in a short time even when a weakly alkaline developer is used, productivity of a cured product such as a photo-etching spacer can be improved. In particular, at said R 4 In the case of an organic group, the alkali-soluble resin a or B of the present invention has a branched structure of a side chain, and therefore, even in the case of thickening, a cured film excellent in development adhesion and resolution can be obtained. For this reason, although not being bound by theory, it is thought that the reason is that R is due to 3 Or R is 3 The terminal carboxyl group tends to face the main chain because of the 'long length (large number of atoms)' and the number of carboxyl groups which can participate in adhesion to the substrate increases. Further, it is thought that this is because, in R 4 In the case of an organic group, the side chain of the alkali-soluble resin A or B is branched, so that R 3 Or R is 3 The carboxyl group at the terminal of the' terminal is more likely to face the main chain, and the number of carboxyl groups involved in adhesion to the substrate increases.
Detailed Description
The alkali-soluble resin A of the present invention contains one or more kinds of repeating structural units X represented by the following general formula (1).
In the formula (1), R 1 Is hydrogen or methyl, R 2 Is a linking group having 1 or more carbon atoms, R 3 Is an organic group represented by the following general formula (2) bonded to a carbon atom of the linking group, R 4 Is a hydroxyl or organic group bonded to a carbon atom of the linking group;
in the formula (2), R 5 Is a parent material with 3-8 carbon atoms and contains a hetero atomAn organic group of a child or an organic group of a parent having 2 to 7 carbon atoms and having a carboxyl group.
The alkali-soluble resin B of the present invention contains a repeating structural unit X 'represented by the following general formula (1'), but does not contain a repeating structural unit having branched side chains each having 2 to 3 terminals each ending with a radical polymerizable substituent.
In the formula (1'), R 1 Is hydrogen or methyl, R 2 Is a linking group having 1 or more carbon atoms, R 3 'is an organic group represented by the following general formula (2') bonded to a carbon atom of the linking group, R 4 Is a hydroxyl or organic group bonded to a carbon atom of the linking group;
in the formula (2'), R 5 ' is a hydrocarbon group having 2 to 7 carbon atoms as a precursor, an organic group having 3 to 8 carbon atoms as a precursor and containing a hetero atom, or an organic group having 2 to 7 carbon atoms as a precursor and having a carboxyl group.
In the present invention, (meth) propylene means propylene or methacrylic, (meth) acryl means acryl or methacryl, (meth) acrylic means acrylic or methacrylic, and (meth) acrylic ester means acrylic ester or methacrylic ester. In the present invention, the carbon number of the parent body means the carbon number of the group which becomes the main skeleton except the substituent.
In the general formula (1) or (1'), the R 2 Is a linking group having 1 or more carbon atoms, and is not particularly limited as long as R is a group capable of binding 3 The R is 4 Or said R 3 ' and R as described 4 A group having 1 or more carbon atoms and being bonded to an oxygen atom of an ester bond. Examples of the linking group include: straight-chain or branched aliphatic saturated or unsaturated hydrocarbon group, alicyclic ringSaturated or unsaturated hydrocarbon groups (including bridged rings), condensed rings, aromatic hydrocarbon groups, organic groups in which a part of carbon atoms constituting the hydrocarbon groups is substituted with hetero atoms (for example, oxygen atoms, nitrogen atoms, sulfur atoms, and the like), and organic groups in which two or more of them are bonded, and the like. In addition, the hydrocarbon group or the organic group may have various substituents (for example, halogen group, hydroxyl group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, aryl group, and the like) or functional groups (for example, ester bond, amide bond, ether bond, thioether bond, urethane bond, and the like).
The linking group is preferably a hydrocarbon group having 1 to 10 carbon atoms as a parent or an organic group having 1 to 10 carbon atoms as a parent and containing a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, or the like). The linking group is more preferably a hydrocarbon group having 1 to 7 carbon atoms as a parent or an organic group having 1 to 7 carbon atoms as a parent and containing a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, or the like). In addition, in the case where the linking group contains a heteroatom, the heteroatom of the linking group is present in the general formula (1) or (1') except for the R 3 Or R is 3 Part other than the bonding part of the 'and the' other than the R 4 "and" a portion other than a bonding portion with an oxygen atom of an ester bond ". The linking group is preferably a linear or branched aliphatic saturated or unsaturated hydrocarbon group having 2 to 7 carbon atoms in the matrix, an alicyclic saturated or unsaturated hydrocarbon group having 3 to 7 carbon atoms in the matrix, a hydrocarbon group having 4 to 7 carbon atoms in the matrix and bonded to an alicyclic saturated or unsaturated hydrocarbon group, a hydrocarbon group having 5 to 7 carbon atoms in the matrix and bonded to an alicyclic saturated or unsaturated hydrocarbon group, or an organic group having 2 to 7 carbon atoms in the matrix and containing an ether bond.
In the above general formula (1), the R 3 Is with said R 2 An organic group represented by the general formula (2) to which a carbon atom of the linking group is bonded. In the general formula (2), the R 5 Is a precursor having 3 to 8 carbon atoms and containing hetero atoms (e.g. oxygen, nitrogenAtoms, sulfur atoms, etc.), or an organic group having a carboxyl group and having 2 to 7 carbon atoms as a parent. The R is 5 Preferably, the organic group having 2 to 7 carbon atoms and a carboxyl group is used as the precursor. At said R 5 In the case of having a carboxyl group, the number of carboxyl groups is not particularly limited, and is preferably 1 to 2. The organic group may have various substituents (e.g., halogen, hydroxyl, carboxyl, amino, alkyl, alkenyl, alkoxy, aryl, etc.) or functional groups (e.g., ester, amide, ether, thioether, urethane, etc.).
The organic group represented by the above general formula (2) is preferably any one of the following organic groups.
In the above general formula (1'), the R 3 ' is bonded to the R 2 An organic group represented by the general formula (2') above, wherein the linking group has a carbon atom. In the general formula (2'), the R 5 ' is a hydrocarbon group having 2 to 7 carbon atoms as a precursor, an organic group having 3 to 8 carbon atoms as a precursor and containing a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, or the like), or an organic group having 2 to 7 carbon atoms as a precursor and having a carboxyl group. The R is 5 The "preferred" is a hydrocarbon group having 2 to 7 carbon atoms as a precursor or an organic group having 2 to 7 carbon atoms as a precursor and having a carboxyl group. At said R 5 In the case where the "carboxyl group" is present, the number of carboxyl groups is not particularly limited, and is preferably 1 to 2. Examples of the hydrocarbon group include: and a linear or branched aliphatic saturated or unsaturated hydrocarbon group, an alicyclic saturated or unsaturated hydrocarbon group (including a bridged ring and a condensed ring), an aromatic hydrocarbon group, a hydrocarbon group in which two or more of them are bonded, and the like. The hydrocarbon group or the organic group may have various substituents (for example, halogen group, hydroxyl group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, aryl group, etc.) or functional groups (for example, ester bond, amide bond, ether bond, thioether bond, urethane bond, etc.).
The organic group represented by the above general formula (2') is preferably any one of the following organic groups.
In the general formula (2) or (2'), R is 5 Or R is 5 ' is preferably an organic group represented by the following general formula (3).
In the formula (3), R 6 R is R 7 R is independently a hydrocarbon group having 1 to 6 carbon atoms as a parent 6 R is R 7 The total carbon number of the parent is 3-8.
Examples of the hydrocarbon group include: linear or branched aliphatic saturated or unsaturated hydrocarbon groups, aromatic hydrocarbon groups, alicyclic saturated or unsaturated hydrocarbon groups, and the like. The hydrocarbyl group may have various substituents (e.g., halo, hydroxy, carboxyl, amino, alkyl, alkenyl, alkoxy, aryl, and the like).
Examples of the organic group represented by the general formula (3) include the following organic groups.
Preferably said R 6 R is R 7 R is independently a hydrocarbon group having 1 to 5 carbon atoms as a parent 6 R is R 7 The total carbon number of the parent is 3-7.
The organic group represented by the above general formula (2) or (2') is preferably any one of the following organic groups.
In the general formula (1) or (1'), the R 4 Is with said R 2 A hydroxyl group or an organic group bonded to a carbon atom of the linking group. At said R 4 In the case of hydroxyl group, it is further proposedHigh developability. In addition, at R 4 In the case of an organic group, the organic group may be further provided with characteristics (for example, developability, adhesion, solubility, and the like) derived from the organic group. The organic group is not particularly limited, and examples thereof include: a linear or branched aliphatic saturated or unsaturated hydrocarbon group, an alicyclic saturated or unsaturated hydrocarbon group (including bridged or condensed rings), an aromatic hydrocarbon group, an organic group in which a part of carbon atoms constituting the hydrocarbon group is substituted with a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, or the like), an organic group in which two or more of them are bonded, or the like. In addition, the hydrocarbon group or the organic group may have various substituents (for example, halogen group, hydroxyl group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, aryl group, and the like) or functional groups (for example, ester bond, amide bond, ether bond, thioether bond, urethane bond, and the like).
The R is 4 The organic group of (2) preferably contains one or more functional groups selected from the group consisting of acryloyloxy, methacryloyloxy, acyloxy, amidooxy, alkoxy, aryloxy, amino, and nitrogen-containing heterocycle, and more preferably is an organic group represented by acryloyloxy, methacryloyloxy, or any one of the following formulas.
Wherein R is 10 R is R 11 Separately and independently represent paragraph [0039 ]]An organic group as described.
In addition, the R 4 Preferably with said R 2 Hydroxyl group bonded to a carbon atom of the linking group, acryloyloxy group, methacryloyloxy group, or an organic group represented by the following general formula (4).
In the formula (4), R 8 Is hydrogen or methyl, R 9 Is a hydrocarbon group having 1 to 5 carbon atoms as a parent or a hydrocarbon group having 1 to 5 carbon atoms as a parentAnd an organic group containing a heteroatom.
In the above general formula (4), the R 9 Is a hydrocarbon group having 1 to 5 carbon atoms as a parent or an organic group having 1 to 5 carbon atoms as a parent and containing a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, or the like). In the case where the organic group contains a heteroatom, the heteroatom of the organic group is present in the general formula (4) in "a portion other than the bonding portion with the nitrogen atom of the urethane bond" and "a portion other than the bonding portion with the oxygen atom of the (meth) acryloyloxy group". Examples of the "hydrocarbon" may include a linear or branched aliphatic saturated or unsaturated hydrocarbon. The hydrocarbon group or the organic group may have various substituents (for example, halogen group, hydroxyl group, carboxyl group, amino group, alkyl group, alkenyl group, alkoxy group, aryl group, etc.) or functional groups (for example, ester bond, amide bond, ether bond, thioether bond, urethane bond, etc.). The R is 9 The hydrocarbon group having 1 to 5 carbon atoms in the matrix is preferable, and ethylene or propylene is more preferable.
Examples of the monomer that forms the basis of the repeating structural unit other than the repeating structural unit X or X' constituting the alkali-soluble resin a or B include: carboxyl group-containing monomers such as (meth) acrylic acid, 2- (meth) acryloyloxyethyl succinic acid, maleic acid and itaconic acid; carboxylic anhydride group-containing monomers such as maleic anhydride and itaconic anhydride; alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, benzyl (meth) acrylate, lauryl (meth) acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, ethoxyethyl (meth) acrylate, and epoxypropyl (meth) acrylate; alicyclic (meth) acrylates such as cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, and dicyclopentenyl (meth) acrylate. In addition, styrene, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide, n-butylmaleimide, gui Jishun-butenediimide, silicone-containing monomers and the like can be used as the comonomer. These monomers may be used either singly or as a combination of two or more.
However, the alkali-soluble resin B does not contain a repeating structural unit (hereinafter also referred to as "repeating structural unit Y") having branched side chains each having 2 to 3 terminals each ending with a radical polymerizable substituent. The repeating structural unit Y is a monomer unit (1) described in International publication No. 2018/169036; specifically, each of the radically polymerizable substituents is substituted, for example, on a hydrocarbon chain (L) bonded to the main chain of the polymer via, for example, a-COO-group. The number of carbon atoms constituting the hydrocarbon chain (L) is, for example, 3 to 5, 3 or 4 or 3. The radical polymerizable substituent is, for example, (meth) acryloyloxy.
The alkali-soluble resin a or B of the present invention can be synthesized, for example, by the following method (1) or method (2) or the like: the method (1) is to react a carboxyl group-containing compound with "a polymer having an epoxy group in a side chain obtained by polymerizing a monomer composition containing an epoxy group-containing (meth) acrylate", convert to a side chain having a hydroxyl group, and then react a carboxylic anhydride with the hydroxyl group; in the method (2), a compound having an ethylenically unsaturated group and a carboxyl group is reacted with a "polymer having an epoxy group in a side chain obtained by polymerizing a monomer composition containing an epoxy group-containing (meth) acrylate" to convert the polymer into a side chain having a hydroxyl group and an ethylenically unsaturated group, and then a compound having a functional group reactive with a hydroxyl group such as an isocyanato group is reacted with the hydroxyl group, and further a compound having a functional group reactive with an ethylenically unsaturated group such as a hydroxyl group, a thiol group, and an amino group and a carboxyl group is reacted with the ethylenically unsaturated group.
The alkali-soluble resin A or B may be a homopolymer composed of the repeating structural unit X or X ', or may be a random copolymer, a block copolymer, an alternating copolymer or a periodic copolymer composed of the repeating structural unit X or X' and other repeating structural units.
In the alkali-soluble resin a or B, the content of the repeating structural unit X or X' is not particularly limited, but is preferably 5 to 50 mol%, more preferably 5 to 25 mol% in all the repeating structural units, from the viewpoint of forming a cured film excellent in development adhesion and resolution even in the case of thickening and from the viewpoint of enabling development in a short time even in the case of using a weakly alkaline developer.
The weight average molecular weight of the alkali-soluble resin a or B is not particularly limited, but is preferably 5000 to 40000, more preferably 5000 to 20000, from the viewpoints of sensitivity and developability. The weight average molecular weight is a value obtained by converting polystyrene measured by Gel Permeation Chromatography (GPC) and is measured based on JIS 7252-4. The weight average molecular weight described in examples described later is also a value obtained from the description of this item.
The acid value of the alkali-soluble resin a or B is not particularly limited, but is preferably 20mgKOH/g to 120mgKOH/g, more preferably 20mgKOH/g to 80mgKOH/g, from the viewpoint of enabling development in a short time even in the case of using a weakly alkaline developer.
The photosensitive resin composition of the present invention comprises at least the alkali-soluble resin A and/or B, a polymerizable monomer, and a photopolymerization initiator.
The content ratio (total in the case of the combination) of the alkali-soluble resin a and/or B with respect to all solid components in the photosensitive resin composition is not particularly limited, but is usually about 40 to 90 mass%, preferably 40 to 80 mass%, more preferably 50 to 70 mass% from the viewpoint of forming a cured film excellent in development adhesion and resolution even in the case of thickening and from the viewpoint of enabling development in a short time even in the case of using a weakly alkaline developer.
The polymerizable monomer is not particularly limited, and examples thereof include: monofunctional monomers such as nonylphenyl carbitol (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 2-ethylhexyl carbitol (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and N-vinylpyrrolidone; polyfunctional aromatic vinyl monomers such as divinylbenzene, diallyl phthalate and diallyl phenylphosphonate (diallyl benzene phosphonate); and multifunctional (meth) acrylates such as (di) ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and tri (meth) acrylate of tris (hydroxyethyl) isocyanurate. These polymerizable monomers may be used singly or in combination of two or more.
The content of the polymerizable monomer is not particularly limited, and is preferably 30 to 100 parts by mass, more preferably 40 to 80 parts by mass, and still more preferably 50 to 70 parts by mass, relative to 100 parts by mass (total in the case of the combination) of the alkali-soluble resin a and/or B, from the viewpoint of sufficiently obtaining the effect of the present invention.
The photopolymerization initiator is not particularly limited, and examples thereof include: benzoin such as benzoin methyl ether and benzoin ethyl ether, and alkyl ethers thereof; acetophenones such as acetophenone, 2-dimethoxy-2-phenylacetophenone, and 1, 1-dichloroacetophenone; anthraquinones such as 2-methylanthraquinone, 2-pentylalnthraquinone, 2-t-butylanthraquinone, and 1-chloroanthraquinone; 9-thioxanthones such as 2, 4-dimethyl 9-thioxanthone, 2, 4-diisopropyl 9-thioxanthone and 2-chloro 9-thioxanthone; ketals such as acetophenone dimethyl ketal and diphenyl ethylene dione dimethyl ketal; benzophenone such as benzophenone; 2-methyl-1- [4- (methylthio) phenyl ] -2-linyl-propan-1-one or 2-benzyl-2-dimethylamino-1- (4-linylphenyl) -butanone-1; acyl phosphine oxides, xanthones, and the like. These photopolymerization initiators may be used alone or in combination of two or more.
The content of the photopolymerization initiator is not particularly limited, but is preferably 0.1 to 5 parts by mass, more preferably 0.2 to 4 parts by mass, and still more preferably 0.5 to 3 parts by mass, based on 100 parts by mass (total in the case of the combination) of the alkali-soluble resins a and/or B.
A photopolymerization initiator aid may be added to the photosensitive resin composition. Examples of the photopolymerization initiator include: trifunctional thiol compounds such as 1,3, 5-tris (3-mercaptopropionyloxyethyl) isocyanurate, 1,3, 5-tris (3-mercaptobutoxyethyl) isocyanurate (Karenz MT (registered trademark) NR1 manufactured by Zhaokogaku corporation), trimethylolpropane tris (3-mercaptopropionate); tetrafunctional thiol compounds such as pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptobutyrate) (Karenz MT (registered trademark) PEI manufactured by Showa Denko Co., ltd.); and multifunctional mercaptans such as hexafunctional mercaptan compounds such as dipentaerythritol hexa (3-propionate). These photopolymerization initiator may be used singly or in combination of two or more.
A thermal polymerization initiator may also be added to the photosensitive resin composition. Examples of the thermal polymerization initiator include: organic peroxides such as cumene hydroperoxide, diisopropylbenzene peroxide, di-t-butyl peroxide, lauryl peroxide, benzoyl peroxide, t-butyl peroxyisopropyl carbonate, t-butyl peroxy (2-ethylhexanoate), t-amyl peroxy (2-ethylhexanoate) and the like; azo compounds such as 2,2' -azobis (isobutyronitrile), 1' -azobis (cyclohexanecarbonitrile) (1, 1' -azobis (cyclohexanecarbonitrile)), 2' -azobis (2, 4-dimethylvaleronitrile), and dimethyl 2,2' -azobis (2-methylpropionate). These thermal polymerization initiators may be used either singly or as a combination of two or more.
The photosensitive resin composition may be added: radical polymerizable oligomers such as unsaturated polyesters, epoxy acrylates, urethane acrylates, and polyester acrylates, and curable resins such as epoxy resins.
The photosensitive resin composition may also contain a solvent. Examples of the solvent include: tetrahydrofuran, twoEthers such as alkyl, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and the like; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; esters such as ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, and 3-methoxybutyl acetate; methanolAlcohols such as ethanol, isopropanol, n-butanol, ethylene glycol monomethyl ether, and propylene glycol monomethyl ether; aromatic hydrocarbons such as toluene, xylene, and ethylbenzene; chloroform, dimethyl sulfoxide, and the like. These solvents may be used either singly or as a combination of two or more. The content of the solvent may be appropriately set according to the optimum viscosity when the composition is used. />
The photosensitive resin composition may contain, within a range that does not impair the effects of the present invention: aluminum hydroxide, talc, clay, barium sulfate and other fillers, dyes, pigments, defoamers, coupling agents, leveling agents, sensitizers, release agents, lubricants, plasticizers, antioxidants, ultraviolet absorbers, flame retardants, polymerization inhibitors, thickeners, dispersants and other known additives.
The cured product of the present invention can be obtained by curing the photosensitive resin composition. Examples of the method for producing the cured product include the following methods: the photosensitive resin composition is injected into a molding die (resin die), or the photosensitive resin composition is coated on a base material (substrate) or various functional layers to be formed into a desired shape, and then the photosensitive resin composition is cured by irradiation with light (e.g., ultraviolet rays). The curing conditions are appropriately adjusted according to the photosensitive resin composition used.
The cured product can be preferably used as a photolithographic spacer, a spacer material, a lens material, an interlayer insulating film material, a protective film material, an optical waveguide material, or a planarizing film material, and particularly can be preferably used as a photolithographic spacer.
The method for forming the photo spacer is not particularly limited, and for example, the photosensitive resin composition may be coated on a substrate such as glass or transparent plastic film, dried to form a coating film, and then formed by photolithography. In the photolithography, for example, a photomask is arranged on a coating film, ultraviolet rays are irradiated thereto, the coating film is thereby photo-cured, an alkaline solution is dispersed in the ultraviolet-irradiated coating film, unexposed portions are dissolved and removed, and the remaining exposed portions are washed with water and developed, thereby forming a photolithographic spacer. Then, post baking may also be performed.
By using the photosensitive resin composition of the present invention, a photo-resist spacer having a film thickness of 10 μm or more, 20 μm or more, 30 μm or more, and further 50 μm or more can be produced with high development adhesion and high resolution. Further, by using the photosensitive resin composition of the present invention, a photo spacer having an aspect ratio (aspect ratio) of 4.0 or more can be produced. In addition, the photosensitive resin composition of the present invention can be developed in a short time even when a weakly alkaline developer is used, and thus a photolithographic spacer can be produced with good productivity.
Examples
The present invention will be described below by way of examples, but the present invention is not limited to these examples.
Synthesis example 1 Synthesis of alkali-soluble resin 1
The alkali-soluble resin 1 containing the following repeating structural units a and X1 was synthesized by the following production method.
To a glass flask equipped with a heating/cooling/stirring apparatus, a reflux condenser, and a nitrogen inlet tube, 100g of glycidyl methacrylate and 212g of propylene glycol monomethyl ether acetate were added. The gas phase portion in the system was replaced with nitrogen, 17g of 2,2' -azobis (2, 4-dimethylvaleronitrile) was then added thereto, and the mixture was heated at 80℃and reacted at the same temperature for 8 hours. To the obtained solution were further added 53.2g of acrylic acid, 1.0g of triphenylphosphine, 0.02g of hydroquinone and 6.0g of propylene glycol monomethyl ether acetate, and the mixture was reacted at 100℃for 16 hours. After the reaction, 3.7g of succinic anhydride and 13.0g of propylene glycol monomethyl ether acetate were further added to the reaction solution, and reacted at 65℃for 6 hours, thereby obtaining a solution containing 45 mass% of the alkali-soluble resin 1. Molecular weight measurement by GPC gave a weight average molecular weight (Mw) of 7000 for the alkali-soluble resin 1. The molecular weight was measured by gel permeation chromatography (manufactured by Tosoh corporation, product number: HLC-8120, column: G-5000HXL and G-3000HXL were connected, detector: RI, and mobile phase: tetrahydrofuran). Weight average molecular weight was also measured in the same manner as follows. In addition, the acid value of the alkali-soluble resin 1 was 21mgKOH/g.
Synthesis example 2 Synthesis of alkali-soluble resin 2
A solution containing 45 mass% of the alkali-soluble resin 2 was obtained in the same manner as in synthesis example 1, except that the amount of succinic anhydride added to the reaction solution was changed to 11.0g and the amount of propylene glycol monomethyl ether acetate added was changed to 22.0 g. The weight average molecular weight (Mw) of the alkali-soluble resin 2 was 7000 as a result of molecular weight measurement by GPC. In addition, the acid value of the alkali-soluble resin 2 was 54mgKOH/g.
Synthesis example 3 Synthesis of alkali-soluble resin 3
A solution containing 45 mass% of the alkali-soluble resin 3 was obtained in the same manner as in synthesis example 1, except that the amount of succinic anhydride added to the reaction solution was changed to 18.5g and the amount of propylene glycol monomethyl ether acetate added was changed to 31.0 g. The weight average molecular weight (Mw) of the alkali-soluble resin 3 was 7000 as a result of molecular weight measurement by GPC. In addition, the acid value of the alkali-soluble resin 3 was 66mgKOH/g.
Synthesis example 4 Synthesis of alkali-soluble resin 4
The alkali-soluble resin 4 containing the following repeating structural units a and X1 was synthesized by the following production method.
To a glass flask equipped with a heating/cooling/stirring apparatus, a reflux condenser, and a nitrogen inlet tube, 100g of glycidyl methacrylate and 150g of propylene glycol monomethyl ether acetate were added. The gas phase portion in the system was replaced with nitrogen, and then 5.2g of 2,2' -azobis (2, 4-dimethylvaleronitrile) was added thereto, and the reaction was carried out at 80℃for 8 hours. To the obtained solution were further added 53.2g of acrylic acid, 2.0g of triphenylphosphine, 0.02g of hydroquinone and 1.0g of propylene glycol monomethyl ether acetate, and the mixture was reacted at 100℃for 7 hours. After the reaction, 11g of succinic anhydride and 9.3g of propylene glycol monomethyl ether acetate were further added to the reaction solution, and the mixture was reacted at 65℃for 6 hours, thereby obtaining a solution containing 52% by mass of the alkali-soluble resin 4. Molecular weight measurement by GPC gave a weight average molecular weight (Mw) of 13000 for alkali-soluble resin 4. In addition, the acid value of the alkali-soluble resin 4 was 51mgKOH/g.
Synthesis example 5 Synthesis of alkali-soluble resin 5
The alkali-soluble resin 5 including the following repeating structural unit A, B and X2 was synthesized by the following production method.
To a glass flask equipped with a heating/cooling/stirring apparatus, a reflux condenser, and a nitrogen inlet tube, 100g of glycidyl methacrylate and 160g of propylene glycol monomethyl ether acetate were added. The gas phase portion in the system was replaced with nitrogen, 7.5g of 2,2' -azobis (2, 4-dimethylvaleronitrile) was then added, and the reaction was carried out at 80℃for 8 hours. To the obtained solution were further added 53.2g of acrylic acid, 0.3g of triphenylphosphine and 0.02g of hydroquinone, and the mixture was reacted at 100℃for 15 hours. After the reaction, 87g of 2-isocyanatoethyl methacrylate (Karenz MOI, manufactured by Showa Denko Co., ltd.), 0.01g of hydroquinone and 0.1g of N, N' -dimethylbenzylamine were further added to the reaction solution, and the mixture was reacted at 65℃for 15 hours. After the reaction, 26.0g of thioglycollic acid, 50g of propylene glycol monomethyl ether acetate, 0.003g of hydroquinone, 0.5g of p-methoxyphenol and 0.5g of N, N' -dimethylbenzylamine were further added to the reaction solution, and reacted at 70℃for 20 hours to obtain a solution containing 50% by mass of alkali-soluble resin 5. Molecular weight measurement by GPC gave a weight average molecular weight (Mw) of 28000 for alkali-soluble resin 5. In addition, the acid value of the alkali-soluble resin 5 was 59mgKOH/g.
Synthesis example 6 Synthesis of alkali-soluble resin 6
The alkali-soluble resin 6 containing the following repeating structural units a and X3 was synthesized by the following production method.
To a glass flask equipped with a heating/cooling/stirring apparatus, a reflux condenser, and a nitrogen inlet tube, 100g of glycidyl methacrylate and 212g of propylene glycol monomethyl ether acetate were added. The gas phase portion in the system was replaced with nitrogen, 17g of 2,2' -azobis (2, 4-dimethylvaleronitrile) was then added thereto, and the mixture was heated at 80℃and reacted at the same temperature for 8 hours. To the obtained solution were further added 53.2g of acrylic acid, 1.0g of triphenylphosphine, 0.02g of hydroquinone and 6.0g of propylene glycol monomethyl ether acetate, and the mixture was reacted at 100℃for 16 hours. After the reaction, 18.2g of 5-norbornene-2, 3-dicarboxylic anhydride and 31.0g of propylene glycol monomethyl ether acetate were further added to the reaction solution, and reacted at 65℃for 19 hours, thereby obtaining a solution containing 45 mass% of the alkali-soluble resin 6. Molecular weight measurement by GPC gave a weight average molecular weight (Mw) of 8000 for the alkali-soluble resin 6. In addition, the acid value of the alkali-soluble resin 6 was 58mgKOH/g.
Synthesis example 7 Synthesis of alkali-soluble resin 7
To a glass flask equipped with a heating/cooling/stirring apparatus, a reflux condenser, and a nitrogen inlet tube were added 25.0g of methacrylic acid, 12.8g of methyl methacrylate, 20.2g of dicyclopentanyl methacrylate, and 94.6g of propylene glycol monomethyl ether acetate, 6.4g of 2,2' -azobis (2, 4-dimethylvaleronitrile) was added, and the mixture was reacted at 80℃for 8 hours under a nitrogen atmosphere. To the obtained solution, 12.3g of glycidyl methacrylate, 0.2g of hydroquinone and 2.5g of propylene glycol monomethyl ether acetate were further added, and reacted at 100℃for 19 hours to obtain a solution containing 45 mass% of the alkali-soluble resin 7. Molecular weight measurement by GPC resulted in the weight average molecular weight (Mw) of the alkali-soluble resin 7 being 11800. In addition, the acid value of the alkali-soluble resin 7 was 107mgKOH/g.
Synthesis example 8 Synthesis of alkali-soluble resin 8
To a glass flask equipped with a heating/cooling/stirring apparatus, a reflux condenser, and a nitrogen inlet tube were added 25.0g of methacrylic acid, 22.6g of methyl methacrylate, 18.4g of butyl methacrylate, and 99.0g of propylene glycol monomethyl ether acetate, and then 5.6g of 2,2' -azobis (2, 4-dimethylvaleronitrile) was added, followed by reaction at 80℃for 8 hours under a nitrogen atmosphere. To the obtained solution were further added 18.4g of glycidyl methacrylate, 0.2g of hydroquinone and 4.3g of propylene glycol monomethyl ether acetate, and reacted at 100℃for 19 hours, thereby obtaining a solution containing 45 mass% of the alkali-soluble resin 8. Molecular weight measurement by GPC gave a weight average molecular weight (Mw) of 10800 for the alkali-soluble resin 8. In addition, the acid value of the alkali-soluble resin 8 was 106mgKOH/g.
Synthesis example 9 Synthesis of alkali-soluble resin 9
To a glass flask equipped with a heating/cooling/stirring apparatus, a reflux condenser, and a nitrogen inlet tube, 100g of glycidyl methacrylate and 212g of propylene glycol monomethyl ether acetate were added. The gas phase portion in the system was replaced with nitrogen, 17g of 2,2' -azobis (2, 4-dimethylvaleronitrile) was then added thereto, and the mixture was heated at 80℃and reacted at the same temperature for 8 hours. To the obtained solution were further added 53.2g of acrylic acid, 1.0g of triphenylphosphine, 0.02g of hydroquinone and 6.0g of propylene glycol monomethyl ether acetate, and reacted at 100℃for 12 hours, thereby obtaining a solution containing 44% by mass of an alkali-soluble resin 9. Molecular weight measurement by GPC gave a weight average molecular weight (Mw) of 9000 for alkali-soluble resin 9. In addition, the acid value of the alkali-soluble resin 9 was 12mgKOH/g.
Synthesis example 10 Synthesis of alkali-soluble resin 10
A solution containing 45 mass% of the alkali-soluble resin 10 was obtained in the same manner as in Synthesis example 6 except that 14.2g of trimellitic anhydride was added instead of 18.2g of 5-norbornene-2, 3-dicarboxylic anhydride and the amount of propylene glycol monomethyl ether acetate added was changed from 31.0g to 26.2 g. Molecular weight measurement by GPC gave a weight average molecular weight (Mw) of 16000 for the alkali-soluble resin 10. In addition, the acid value of the alkali-soluble resin 10 was 62mgKOH/g.
Examples 1 to 7 and comparative examples 1 to 3
[ preparation of photosensitive resin composition ]
A photosensitive resin composition (example 1) having a solid content of 50% was prepared by mixing 100 parts by mass of the solution containing 45% by mass of the alkali-soluble resin 1, 60 parts by mass of dipentaerythritol hexaacrylate (manufactured by Japanese chemical Co., ltd., KAYARAD DPHA), 1.6 parts by mass of a photopolymerization initiator (manufactured by LAMBSON Co., ltd., SPEEDCURE TPO), 1.0 parts by mass of a photopolymerization initiator (BASF Japan Co., ltd., irgacure OXE 01), and 0.2 parts by mass of a surfactant (manufactured by BYK, BYK-307). Photosensitive resin compositions having a solid content of 50% in the composition (examples 2 to 7 and comparative examples 1 to 3) were prepared in the same manner as described above, except that 100 parts by mass of each of the solutions containing the alkali-soluble resins 2 to 10 of each mass% was used instead of 100 parts by mass of the solution containing the alkali-soluble resin 1 of 45 mass%.
[ evaluation of developability ]
The photosensitive resin compositions prepared in examples 1 to 7 and comparative examples 1 to 3 were applied to glass substrates each having a square of 10cm×10cm using a spin coater to form a coating film having a film thickness of 30 μm, and the coating film was heated on a heating plate at 90℃for 2 minutes to completely remove the solvent. Then, for the obtained coating film, 0.3% Na was used 2 CO 3 The aqueous solution was subjected to alkali development, and the development property was evaluated with the time for dissolving and removing the coating film as the shortest development time. The smaller the value, the more excellent the developability is considered. The grades are classified according to the following criteria.
A: the shortest development time is within 60 seconds;
b: the shortest development time exceeds 60 seconds and is within 80 seconds;
c: the shortest development time exceeds 80 seconds and is within 100 seconds;
f: the minimum development time exceeds 100 seconds.
[ production of photolithographic spacer ]
The photosensitive resin compositions prepared in examples 1 to 7 and comparative examples 1 to 3 were applied to glass substrates having a square of 10cm×10cm using a spin coater, and the rotation speed of the spin coater was adjusted so that the height of the photo spacers after formation became 30 μm, to form coating films, and each coating film was heated on a heating plate at 100 ℃ for 2 minutes, to completely remove the solvent. Then, for each of the obtained coating films, a photomask was used at 100mJ/cm by photolithographic spacer formation 2 Light (illuminance in terms of i line was 21 mW/cm) from an ultra-high pressure mercury lamp was irradiated 2 ) Wherein the photolithographic spacer is formedThe photomask had 100 pieces/cm 2 And an opening portion having a diameter of 4 to 30 μm and a scale of 1 μm. The exposure was performed so that the distance between the photomask and the substrate (exposure gap) was 100 μm. Then, 0.3% Na was used 2 CO 3 The aqueous solution was subjected to alkaline development. The development time was 1.5 times the shortest development time measured by the method. After water washing, post baking was performed at 230 ℃ for 30 minutes, thereby forming a photolithographic spacer.
[ evaluation of developing adhesion ]
The line width of the minimum pattern formed without removal by development in the photolithographic spacers formed by the above method was evaluated as development adhesion. The smaller the value, the more excellent the development adhesion is considered. The grades are classified according to the following criteria.
A: the minimum pattern is less than 15 mu m;
b: the minimum pattern is above 15 μm and less than 20 μm;
c: the minimum pattern is more than 20 mu m;
f: cannot be developed.
TABLE 1
As is clear from the results of table 1, when a weakly alkaline developer is used for forming a thick film pattern having a pattern height of about 30 μm, the photosensitive resin compositions of examples 1 to 7 can be developed in a shorter time and a cured film excellent in development adhesion can be formed as compared with the photosensitive resin compositions of comparative examples 1 to 3.
Industrial applicability
The alkali-soluble resin of the present invention and the photosensitive resin composition containing the alkali-soluble resin can be suitably used as a raw material for a photo-etching spacer, a spacer material, a lens material, an interlayer insulating film material, a protective film material, an optical waveguide material or a planarizing film material.
Claims (14)
1. An alkali-soluble resin comprising one or more kinds of repeating structural units X represented by the following general formula (1),
in the general formula (1), R 1 Is hydrogen or methyl, R 2 Is a linking group having 1 or more carbon atoms, R 3 Is an organic group represented by the following general formula (2) bonded to a carbon atom of the linking group, R 4 Is a hydroxyl or organic group bonded to a carbon atom of the linking group;
in the general formula (2), R 5 Is an organic group having 3 to 8 carbon atoms as a parent or an organic group having 2 to 7 carbon atoms as a parent and having a carboxyl group.
2. An alkali-soluble resin comprising a repeating structural unit X 'represented by the following general formula (1'), but not comprising a repeating structural unit having branched side chains each having 2 to 3 terminals each ending with a radical polymerizable substituent,
in the general formula (1'), R 1 Is hydrogen or methyl, R 2 Is a linking group having 1 or more carbon atoms, R 3 'is an organic group represented by the following general formula (2') bonded to a carbon atom of the linking group, R 4 Is a hydroxyl or organic group bonded to a carbon atom of the linking group;
in the general formula (2'), R 5 ' is a hydrocarbon group having 2 to 7 carbon atoms as a precursor, an organic group having 3 to 8 carbon atoms as a precursor and containing a hetero atom, or an organic group having 2 to 7 carbon atoms as a precursor and having a carboxyl group.
3. The alkali-soluble resin as claimed in claim 1 or 2, wherein the R 2 The linking group of (2) is a hydrocarbon group having 1 to 10 carbon atoms of the parent body, or
And (3) an organic group having 1 to 10 carbon atoms and containing a heteroatom.
4. The alkali-soluble resin as claimed in any one of claims 1 to 3, wherein the R 4 The organic group of (2) is an organic group containing one or more functional groups selected from the group consisting of acryloyloxy, methacryloyloxy, acyloxy, amidooxy, alkoxy, aryloxy, amino, and nitrogen-containing heterocycle.
5. The alkali-soluble resin as claimed in claim 1 or 2, wherein the R 2 Is a hydrocarbon group having 1 to 7 carbon atoms as a parent or an organic group having 1 to 7 carbon atoms and containing a hetero atom as a parent, and
the R is 4 Is with said R 2 Hydroxyl, acryloxy or methacryloxy groups bonded to carbon atoms of the linking group of (c).
6. The alkali-soluble resin as claimed in claim 1, wherein said R 2 The linking group of (a) is a hydrocarbon group having 1 to 7 carbon atoms as a parent or an organic group having 1 to 7 carbon atoms as a parent and containing a hetero atom,
the R is 5 Is an organic group represented by the following formula (3), and
the R is 4 Is with said R 2 Hydroxyl group, acryloyloxy group, methacryloyloxy group bonded to a carbon atom of the linking group of (c), or an organic group represented by the following general formula (4),
in the general formula (3), R 6 R is R 7 R is independently a hydrocarbon group having 1 to 6 carbon atoms as a parent 6 R is R 7 The total carbon number of the parent body of the catalyst is 3-8;
in the general formula (4), R 8 Is hydrogen or methyl, R 9 Is a hydrocarbon group having 1 to 5 carbon atoms as the parent or a carbon as the parentAn organic group having a number of 1 to 5 and containing a hetero atom.
7. The alkali-soluble resin as claimed in claim 2, wherein the R 2 The linking group of (a) is a hydrocarbon group having 1 to 7 carbon atoms as a parent or an organic group having 1 to 7 carbon atoms as a parent and containing a hetero atom,
the R is 5 ' is an organic group represented by the following formula (3), and
the R is 4 Is with said R 2 Hydroxyl group, acryloyloxy group, methacryloyloxy group bonded to a carbon atom of the linking group of (c), or an organic group represented by the following general formula (4),
In the general formula (3), R 6 R is R 7 R is independently a hydrocarbon group having 1 to 6 carbon atoms as a parent 6 R is R 7 The total carbon number of the parent body of the catalyst is 3-8;
in the general formula (4), R 8 Is hydrogen or methyl, R 9 Is a hydrocarbon group having 1 to 5 carbon atoms as a parent or an organic group having 1 to 5 carbon atoms as a parent and containing a hetero atom.
8. The alkali-soluble resin as claimed in any one of claims 1 to 7, wherein the content of the repeating structural unit X or X' is 5 to 50 mol% in all the repeating structural units.
9. The alkali-soluble resin as claimed in any one of claims 1 to 8, wherein the acid value of the alkali-soluble resin is 20mgKOH/g to 120mgKOH/g.
10. The alkali-soluble resin according to any one of claims 1 to 9, wherein the alkali-soluble resin has a weight average molecular weight of 5000 to 40000.
11. A photosensitive resin composition comprising at least the alkali-soluble resin according to any one of claims 1 to 10, a polymerizable monomer, and a photopolymerization initiator.
12. A cured product obtained by the photosensitive resin composition according to claim 11.
13. The cured product according to claim 12, wherein the cured product is a photo spacer, a spacer material, a lens material, an interlayer insulating film material, a protective film material, an optical waveguide material, or a planarizing film material.
14. An image display device comprising the cured product according to claim 12 or 13.
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| JP2021018060 | 2021-02-08 | ||
| JP2021-018060 | 2021-02-08 | ||
| PCT/JP2022/004685 WO2022168974A1 (en) | 2021-02-08 | 2022-02-07 | Alkali-soluble resin, photosensitive resin composition, cured product, and image display device |
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| CN116867822A true CN116867822A (en) | 2023-10-10 |
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| JP (1) | JPWO2022168974A1 (en) |
| KR (1) | KR20230128119A (en) |
| CN (1) | CN116867822A (en) |
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| TW202330639A (en) * | 2021-11-16 | 2023-08-01 | 日商大阪有機化學工業股份有限公司 | Photosensitive resin composition, cured product and image display device |
| WO2024122200A1 (en) * | 2022-12-09 | 2024-06-13 | 株式会社レゾナック | Photosensitive resin composition, cured resin film, and image display device |
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| GB1464250A (en) * | 1973-12-27 | 1977-02-09 | Ciba Geigy Ag | Acrylate derivatives and their use as anaerobically-curing adhesives |
| JPS582308A (en) * | 1981-06-19 | 1983-01-07 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Polymeric composition |
| JP4989435B2 (en) * | 2007-12-10 | 2012-08-01 | 昭和電工株式会社 | Photosensitive resin and photosensitive resin composition |
| WO2009084373A1 (en) * | 2007-12-28 | 2009-07-09 | Sumitomo Chemical Company, Limited | Fluorine-containing compound, fluorine-containing polymer, and composition and film each containing the polymer |
| JP2013115262A (en) | 2011-11-29 | 2013-06-10 | Sharp Corp | Photoelectric conversion element |
| JP2019124929A (en) | 2018-01-18 | 2019-07-25 | 東レ株式会社 | Negative photosensitive resin composition, and photospacer and image display device including the same |
| WO2019165425A1 (en) * | 2018-02-26 | 2019-08-29 | The Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Antimicrobial gallium compounds and methods |
| JP7347442B2 (en) * | 2018-11-08 | 2023-09-20 | 株式会社レゾナック | Copolymer and resin composition containing the copolymer |
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