WO2013032190A1 - Résine insaturée photopolymérisable, composition de résine photosensible la comprenant, et espaceur protégeant de la lumière et dispositif d'affichage à cristaux liquides formés de ceux-ci - Google Patents
Résine insaturée photopolymérisable, composition de résine photosensible la comprenant, et espaceur protégeant de la lumière et dispositif d'affichage à cristaux liquides formés de ceux-ci Download PDFInfo
- Publication number
- WO2013032190A1 WO2013032190A1 PCT/KR2012/006802 KR2012006802W WO2013032190A1 WO 2013032190 A1 WO2013032190 A1 WO 2013032190A1 KR 2012006802 W KR2012006802 W KR 2012006802W WO 2013032190 A1 WO2013032190 A1 WO 2013032190A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- glycidyl ether
- group
- anhydride
- black
- epoxy
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 56
- 229920005989 resin Polymers 0.000 title claims abstract description 48
- 239000011347 resin Substances 0.000 title claims abstract description 48
- 125000006850 spacer group Chemical group 0.000 title abstract description 35
- 239000004973 liquid crystal related substance Substances 0.000 title description 12
- 239000012860 organic pigment Substances 0.000 claims abstract description 35
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 103
- 239000004593 Epoxy Substances 0.000 claims description 68
- -1 methyl himic anhydride Chemical compound 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 33
- 229920000647 polyepoxide Polymers 0.000 claims description 25
- 239000003822 epoxy resin Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 150000003951 lactams Chemical class 0.000 claims description 21
- 239000001023 inorganic pigment Substances 0.000 claims description 20
- 150000008065 acid anhydrides Chemical class 0.000 claims description 19
- 239000006229 carbon black Substances 0.000 claims description 19
- 150000007519 polyprotic acids Polymers 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000003700 epoxy group Chemical group 0.000 claims description 11
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 229940049920 malate Drugs 0.000 claims description 10
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 5
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 4
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 claims description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 4
- 229940014800 succinic anhydride Drugs 0.000 claims description 4
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 claims description 3
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 3
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- 229920000767 polyaniline Polymers 0.000 claims description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 claims description 2
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 claims description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- NQFUSWIGRKFAHK-UHFFFAOYSA-N 2,3-epoxypinane Chemical compound CC12OC1CC1C(C)(C)C2C1 NQFUSWIGRKFAHK-UHFFFAOYSA-N 0.000 claims description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 2
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 claims description 2
- KQXZMAACKJIRJE-UHFFFAOYSA-N 2-(2-methoxyethoxymethyl)oxirane Chemical compound COCCOCC1CO1 KQXZMAACKJIRJE-UHFFFAOYSA-N 0.000 claims description 2
- AQKDMKKMCVJJTC-UHFFFAOYSA-N 2-(2-methylpropoxymethyl)oxirane Chemical compound CC(C)COCC1CO1 AQKDMKKMCVJJTC-UHFFFAOYSA-N 0.000 claims description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims description 2
- NPKKFQUHBHQTSH-UHFFFAOYSA-N 2-(decoxymethyl)oxirane Chemical compound CCCCCCCCCCOCC1CO1 NPKKFQUHBHQTSH-UHFFFAOYSA-N 0.000 claims description 2
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 claims description 2
- INSCMIFABOJDRE-UHFFFAOYSA-N 2-(heptoxymethyl)oxirane Chemical compound CCCCCCCOCC1CO1 INSCMIFABOJDRE-UHFFFAOYSA-N 0.000 claims description 2
- YZUMRMCHAJVDRT-UHFFFAOYSA-N 2-(hexadecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCCCOCC1CO1 YZUMRMCHAJVDRT-UHFFFAOYSA-N 0.000 claims description 2
- JPEGUDKOYOIOOP-UHFFFAOYSA-N 2-(hexoxymethyl)oxirane Chemical compound CCCCCCOCC1CO1 JPEGUDKOYOIOOP-UHFFFAOYSA-N 0.000 claims description 2
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 claims description 2
- KEKXMAURKVLACV-UHFFFAOYSA-N 2-(nonoxymethyl)oxirane Chemical compound CCCCCCCCCOCC1CO1 KEKXMAURKVLACV-UHFFFAOYSA-N 0.000 claims description 2
- HRWYHCYGVIJOEC-UHFFFAOYSA-N 2-(octoxymethyl)oxirane Chemical compound CCCCCCCCOCC1CO1 HRWYHCYGVIJOEC-UHFFFAOYSA-N 0.000 claims description 2
- SNALIOQALXUVIF-UHFFFAOYSA-N 2-(pentadecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCCOCC1CO1 SNALIOQALXUVIF-UHFFFAOYSA-N 0.000 claims description 2
- IQCASZIDTNHBIW-UHFFFAOYSA-N 2-(pentoxymethyl)oxirane Chemical compound CCCCCOCC1CO1 IQCASZIDTNHBIW-UHFFFAOYSA-N 0.000 claims description 2
- QNYBOILAKBSWFG-UHFFFAOYSA-N 2-(phenylmethoxymethyl)oxirane Chemical compound C1OC1COCC1=CC=CC=C1 QNYBOILAKBSWFG-UHFFFAOYSA-N 0.000 claims description 2
- SYFZCLMMUNCHNH-UHFFFAOYSA-N 2-(prop-2-ynoxymethyl)oxirane Chemical compound C#CCOCC1CO1 SYFZCLMMUNCHNH-UHFFFAOYSA-N 0.000 claims description 2
- NWLUZGJDEZBBRH-UHFFFAOYSA-N 2-(propan-2-yloxymethyl)oxirane Chemical compound CC(C)OCC1CO1 NWLUZGJDEZBBRH-UHFFFAOYSA-N 0.000 claims description 2
- CWNOEVURTVLUNV-UHFFFAOYSA-N 2-(propoxymethyl)oxirane Chemical compound CCCOCC1CO1 CWNOEVURTVLUNV-UHFFFAOYSA-N 0.000 claims description 2
- NVKSMKFBUGBIGE-UHFFFAOYSA-N 2-(tetradecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCOCC1CO1 NVKSMKFBUGBIGE-UHFFFAOYSA-N 0.000 claims description 2
- ZCZCZLVSKGCRTD-UHFFFAOYSA-N 2-(tridecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCOCC1CO1 ZCZCZLVSKGCRTD-UHFFFAOYSA-N 0.000 claims description 2
- HNJSJLKMMRCGKX-UHFFFAOYSA-N 2-(undecoxymethyl)oxirane Chemical compound CCCCCCCCCCCOCC1CO1 HNJSJLKMMRCGKX-UHFFFAOYSA-N 0.000 claims description 2
- AYVQIRLANZOASX-UHFFFAOYSA-N 2-[(2,4-dimethylphenoxy)methyl]oxirane Chemical compound CC1=CC(C)=CC=C1OCC1OC1 AYVQIRLANZOASX-UHFFFAOYSA-N 0.000 claims description 2
- SFJRUJUEMVAZLM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxymethyl]oxirane Chemical compound CC(C)(C)OCC1CO1 SFJRUJUEMVAZLM-UHFFFAOYSA-N 0.000 claims description 2
- DXEHULHXWHEJJD-UHFFFAOYSA-N 2-[(4-butylphenoxy)methyl]oxirane Chemical compound C1=CC(CCCC)=CC=C1OCC1OC1 DXEHULHXWHEJJD-UHFFFAOYSA-N 0.000 claims description 2
- AVWGFHZLPMLKBL-UHFFFAOYSA-N 2-[(4-methoxyphenoxy)methyl]oxirane Chemical compound C1=CC(OC)=CC=C1OCC1OC1 AVWGFHZLPMLKBL-UHFFFAOYSA-N 0.000 claims description 2
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 claims description 2
- AVKQYWUBGXNBCW-UHFFFAOYSA-N 2-[(4-nonylphenoxy)methyl]oxirane Chemical compound C1=CC(CCCCCCCCC)=CC=C1OCC1OC1 AVKQYWUBGXNBCW-UHFFFAOYSA-N 0.000 claims description 2
- MHTUIBIYJWEQKA-UHFFFAOYSA-N 2-[[4-(2-phenylpropan-2-yl)phenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=CC=C1 MHTUIBIYJWEQKA-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- YVCOJTATJWDGEU-UHFFFAOYSA-N 2-methyl-3-phenyloxirane Chemical compound CC1OC1C1=CC=CC=C1 YVCOJTATJWDGEU-UHFFFAOYSA-N 0.000 claims description 2
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- DGQOZCNCJKEVOA-UHFFFAOYSA-N 5-(2,5-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1CC(=O)OC1=O DGQOZCNCJKEVOA-UHFFFAOYSA-N 0.000 claims description 2
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 claims description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 2
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004018 acid anhydride group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
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- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- 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
- C08F290/02—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 end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/064—Polymers containing more than one epoxy group per molecule
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/10—Epoxy resins modified by unsaturated compounds
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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
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- 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
-
- 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
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- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
Definitions
- the present invention relates to a novel photopolymerizable unsaturated resin, a photosensitive resin composition comprising the same, and a light shielding spacer and a liquid crystal display device formed therefrom.
- a liquid crystal display (LCD) device as one type of flat panel display devices, which are currently widely being used, comprises a thin film transistor (TFT) substrate on which pixel electrodes are formed; a color filter substrate on which a common electrode is formed and which faces the TFT substrate; and a liquid crystal layer inserted between the TFT substrate and the color filter substrate.
- TFT thin film transistor
- Such an LCD device displays images in a manner of controlling the amount of light transmitting the liquid crystal layer by applying a voltage to the pixel electrodes and common electrode and rearranging the liquid crystal molecules of the liquid crystal layer.
- a spacer is formed from a photosensitive composition by generally using lithography.
- the spacer should have light-shielding properties in order to prevent malfunction of a TFT as a switching device caused by incident light.
- carbon black be mixed with a photosensitive resin composition.
- an electrical distortion phenomenon is generated by an electrical field applied to the upper and lower substrates, due to the high dielectric constant of carbon black. Therefore, it is required to develop a spacer that has excellent light-shielding properties and a low dielectric constant.
- a photosensitive resin composition used in the preparation of a light-shielding spacer is generally a black composition prepared by mixing dyes having different colors or various types of dyes, wherein said dyes do not easily dissolve in a developing solution. Due to the low solubility in the developing solution, the dyes have problems that developing properties are not good, a long time is consumed in development, or a desired degree of resolution is not obtained. In particular, the importance of resolution is further increased in the case of forming colored independent dot spacer patterns.
- Korean Patent Application Laid-Open No. 2010-0066197 discloses a black photosensitive resin composition, which has good pattern formability, and exhibits high compression displacement and a high recovery rate, as well as a low dielectric constant and superior optical density when forming a thin film.
- said document does not take the resolution of a thin film formed from the composition into consideration, and regards a recovery rate of 70% as being proper, which does not satisfy the level of the recovery rate required by the relevant industry.
- Japanese Patent Application Laid-Open No. 2002-040440 discloses a radiation-sensitive composition, which is capable of forming a spacer having excellent light-shielding properties and high mechanical strength and heat resistance, which is not deformed irreversibly during the sealing of panels, and which does not generate display defects due to a gap difference in liquid crystal layers.
- the document does not take dielectric constant or resolution into consideration in a spacer formed from the composition.
- Patent Document 1 Korean Patent Application Laid-Open No. 2010-0066197
- Patent Document 2 Japanese Patent Application Laid-Open No. 2002-040440
- the first aspect of the present invention provides a photopolymerizable unsaturated resin of a novel structure to be included in a photosensitive resin composition.
- the second aspect of the present invention provides a photosensitive resin composition which includes the novel photopolymerizable unsaturated resin, which can form dot spacer patterns of a size of 10 to 100 ⁇ m due to sufficient solubility in developing solutions before and after light exposure, and which is capable of maintaining excellent light-shielding properties while lowering the dielectric constant of the formed dot spacer patterns.
- the third aspect of the present invention provides a light shielding spacer, which is formed from the photosensitive resin composition, and which has sufficient resolution and excellent elastic recovery ratio.
- the fourth aspect of the present invention provides a liquid crystal display device having the light shielding spacer.
- a photopolymerizable unsaturated resin which is a product (P1) obtained by reacting an epoxy resin(A) represented by formula I with an unsaturated basic acid (B) to form an epoxy adduct (AB), and reacting said adduct with a polybasic acid anhydride (C); or which is a product (P2) obtained by reacting an epoxy resin (A) represented by formula I with an unsaturated basic acid (B) to form an epoxy adduct (AB), reacting said adduct with a polybasic acid anhydride (C) to form a product (P1), and further reacting said product (P1) with a monofunctional or polyfunctional epoxy compound (D).
- P1 obtained by reacting an epoxy resin(A) represented by formula I with an unsaturated basic acid (B) to form an epoxy adduct (AB), and reacting said adduct with a polybasic acid anhydride (C) to form a product (P1), and further reacting said product (P1) with a monofunctional
- carbon labeled with * is replaced with a carbon labeled with * in one selected from the groupconsisting of , , and ;
- L 1 is C 1-10 alkylene, C 3-20 cycloalkylene or C 1-10 alkyleneoxy;
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are the same or different and are each independently selected from the group consisting of hydrogen, C 1-10 alkyl, C 1-10 alkoxy, C 2-10 alkenyl and C 6-14 aryl;
- R 8 is selected from the group consisting of hydrogen, C 1-10 alkyl which is unsubstituted or substituted by halogen or hydroxy, C 2-10 alkenyl and C 6-14 aryl;
- n is an integer of from 0 to 10.
- a photosensitive resin composition comprising the photopolymerizable unsaturated resin; a functional monomer having at least one ethylenically unsaturated bond; a polymerization initiator; a black organic pigment; and a solvent.
- a light shielding spacer formed from the photosensitive resin composition.
- a liquid crystal display device having the spacer.
- a photosensitive resin composition comprising a photopolymerizable unsaturated resin according to the present invention can form a light shielding spacer with dot spacer patterns of a size of 10 to 100 ⁇ m due to sufficient solubility in developing solutions before or after light exposure. Further, the formed light shielding spacer has a low dielectric constant of 8 or less, is excellent in light-shielding property by having an optical density per ⁇ m of 1.0 or more, and has sufficient resolution and excellent elastic recovery ratio.
- the photopolymerizable unsaturated resin which is a product (P1) obtained by the steps of reacting an epoxy resin(A) represented by formula I with an unsaturated basic acid (B) to form an epoxy adduct (AB), and reacting said adduct with a polybasic acid anhydride (C), or a product (P2) obtained by further reacting a monofunctional or polyfunctional epoxy compound (D) with the product (P1).
- the epoxy adduct (AB) can be obtained by reacting the epoxy resin (A) corresponding to 1 equivalent of an epoxy group with the unsaturated basic acid (B) corresponding to 0.1 to 5 equivalents, preferably 0.2 to 2 equivalents, and more preferably 0.4 to 1 equivalent of a carboxyl group according to known addition reactions.
- the photopolymerizable unsaturated resin is a product (P1) obtained by reacting the epoxy adduct (AB) corresponding to 1 equivalent of a hydroxyl group with the polybasic acid anhydride (C) corresponding to 0.1 to 5 equivalents, preferably 0.2 to 2 equivalents, and more preferably 0.4 to 1 equivalent of an acid anhydride group.
- the photopolymerizable unsaturated resin can be obtained by reacting the epoxy adduct (AB) with the polybasic acid anhydride (C) according to known esterification reactions.
- the photopolymerizable unsaturated resin can be obtained by additionally esterifying a monofunctional or polyfunctional epoxy compound (D) with the product (P1) in an amount of 0.1 to 5 equivalents, preferably 0.2 to 2 equivalents and more preferably 0.3 to 1 equivalent of the epoxy group in the monofunctional or polyfunctional epoxy compound with respect to 1 equivalent of the hydroxyl group of the epoxy adduct (AB).
- the esterification between the monofunctional or polyfunctional epoxy compound (D) and a product (P1) obtained by esterifying the epoxy adduct (AB) with the polybasic acid anhydride (C) can occur between a carboxyl group derived from the polybasic acid anhydride (C) and an epoxy group of the monofunctional or polyfunctional epoxy compound (D).
- the photopolymerizable unsaturated resin can be prepared by (i) reacting the epoxy adduct (AB) corresponding to 1 equivalent of a hydroxyl group with the polybasic acid anhydride (C) in such an amount that the sum of an acid anhydride equivalent of the polybasic acid anhydride (C) and an epoxy equivalent in the monofunctional or polyfunctional epoxy compound (D) is not less than 1.0 equivalent, preferably 1.1 to 2.0 equivalents to produce a product, and (ii) further reacting the product with the monofunctional or polyfunctional epoxy compound (D).
- the photopolymerizable unsaturated binder resin has a weight average molecular weight (Mw) preferably ranging from 1,500 to 20,000, more preferably from 3,000 to 15,000. If a weight average molecular weight of the photopolymerizable unsaturated resin is within the above-mentioned range, handling property and pattern formability are good since the flowability of the resin is maintained within a proper range.
- Mw weight average molecular weight
- a photosensitive resin composition according to the present invention may include 0.5 to 50 wt% of a photopolymerizable unsaturated binder resin with respect to the total weight of the photosensitive resin composition except the residual amount of solvent. If the content of the photopolymerizable unsaturated binder resin is within the above-mentioned range, a pattern is easily formed after light exposure and developing processes, the basic physical properties of a light shielding material are satisfied, processing time, such as developing time, and sensitivity are optimized, and characteristics such as compressive properties, chemical resistance and the like are improved.
- Epoxy resin (A) used in the present invention is a compound represented by the following formula 1 having a 9H-xanthene skeleton.
- the 9H-xanthene skeleton structure of the epoxy resin (A) functions as a factor that improves adhesion between a cured body and a substrate, alkali resistance, formability, strength and the like, and increases the resolution of micro-patterns when developing and eliminating non-cured portions.
- carbon labeled with * is replaced with a carbon labeled with * in one selected from the group consisting of , , and ;
- L 1 is a C 1-10 alkylene group, a C 3-20 cycloalkylene group or a C 1-10 alkyleneoxy group;
- R 1 to R 7 are the same as or different from one another and are each independently a hydrogen atom, a C 1-10 alkyl group, a C 1-10 alkoxy group, a C 2-10 alkenyl group or a C 6-14 aryl group;
- n is an integer of from 0 to 10.
- C 1-10 alkylene group may include a methylene group, an ethylene group, a propylene group, an isopropylene group, a butylene group, an isobutylene group, a sec-butylene group, a tert-butylene group, a pentylene group, an isopentylene group, a tert-pentylene group, a hexylene group, a heptylene group, an octylene group, an isooctylene group, a tert-octylene group, a 2-ethylhexylene group, a nonylene group, an isononylene group, a decylene group, and an isodecylene group.
- C 3-20 cycloalkylene group may include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a decalinylene group, and an adamantylene group.
- C 1-10 alkyleneoxy group may include a methyleneoxy group, an ethyleneoxy group, a propyleneoxy group, a butyleneoxy group, a sec-butyleneoxy group, a tert-butyleneoxy group, a pentyleneoxy group, a hexyleneoxy group, a heptyleneoxy group, an octyleneoxy group, and a 2-ethyl-hexyleneoxy group.
- C 1-10 alkyl group may include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a tert-pentyl group, a hexyl group, a heptyl group, an octyl group, an isooctyl group, a tert-octyl group, a 2-ethylhexyl group, a nonyl group, an isononyl group, a decyl group, and an isodecyl group.
- C 1-10 alkoxy group may include a methoxy group, an ethoxy group, a propyloxy group, a butyloxy group, a sec-butoxy group, a tert-butoxy group, a pentoxy group, a hexyloxy group, a heptoxy group, an octyloxy group, and a 2-ethyl-hexyloxy group.
- C 2-10 alkenyl group may include a vinyl group, an allyl group, a butenyl group, and a propenyl group.
- C 6-14 aryl group may include a phenyl group, a tolyl group, a xylyl group, and a naphthyl group.
- An unsaturated basic acid (B) used in the present invention is used in order to improve the sensitivity of a photosensitive resin composition comprising a photopolymerizable unsaturated resin according to the present invention.
- Specific examples of the unsaturated basic acid (B) may include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl methacrylate ⁇ malate, hydroxyethyl acrylate ⁇ malate, hydroxypropyl methacrylate ⁇ malate, hydroxypropyl acrylate ⁇ malate, dicyclopentadiene ⁇ malate, and polyfunctional (meth)acrylate having a carboxyl group and two or more (meth)acryloyl groups, but not limited thereto.
- the unsaturated basic acids can be used alone or in combinations of two or more thereof.
- Acrylic acid, methacrylic acid, and polyfunctional (meth)acrylate having a carboxyl group and two or more (meth)acryloyl groups are preferably used as the unsaturated basic acids.
- the polyfunctional (meth)acrylate having a carboxyl group and two or more (meth)acryloyl groups can be obtained by reacting, e.g., a dibasic acid anhydride or carbonic acid with a polyfunctional (meth)acrylate having a hydroxyl group and two or more (meth)acryloyl groups in a molecule.
- a polybasic acid anhydride (C) used in the present invention is used in order to improve pattern formability, developing properties and developing rate by increasing the acid value of a photosensitive resin composition comprising a photopolymerizable unsaturated resin according to the present invention.
- Examples of the polybasic acid anhydride (C) may include one or more selected from the group consisting of succinic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, 2,2'-3,3'-benzophenone tetra carboxylic dianhydride, 3,3'-4,4'-benzophenone tetra carboxylic dianhydride, ethylene glycol bis(anhydrotrimellitate), glycerol tris(anhydrotrimellitate), phthalic anhydride, hexahydrophthalic anhydride, methyl hydrophthalic anhydride, tetrahydrophthalic anhydride, nadic anhydride, methyl nadic anhydride, trialkyl tetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxy
- a monofunctional epoxy compound used in the present invention is used in order to further improve the developing property of a photosensitive resin composition by controlling the acid value of the photopolymerizable unsaturated resin.
- the solid contents of a photosensitive resin composition according to the present invention have an acid value ranging from 20 to 120 mg KOH/g.
- the amount of a monofunctional epoxy compound is preferably selected to satisfy the above acid value.
- the monofunctional epoxy compound may include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentade
- Polyfunctional epoxy compounds used in the present invention play a role of controlling a developing rate by increasing the molecular weight of the photopolymerizable unsaturated resin.
- polyfunctional epoxy compounds may include polyglycidyl ether of polyvalent alcohol or its alkyleneoxide adduct, polyglycidyl ether of polybasic acid, cyclohexene oxide- or cyclopentene oxide-containing compounds obtained by epoxidating cyclohexene- or cyclopentene-containing compounds with an oxidizer.
- the examples of the polyfunctional epoxy compounds may include: alkylidene bisphenol polyglycidyl ether type epoxy resins such as bisphenol A type epoxy resin, bisphenol B type epoxy resin, bisphenol C type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol M type epoxy resin, bisphenol P type epoxy resin, bisphenol S type epoxy resin, and bisphenol Z type epoxy resin; water-added bisphenol type diglycidyl ethers obtained by adding water to the alkylidene bisphenol polyglycidyl ether type epoxy resins; glycidyl ethers of aliphatic polyvalent alcohol such as ethyleneglycol diglycidyl ether, 1,3-propyleneglycol diglycidyl ether, 1,2-propyleneglycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol dig
- polyfunctional epoxy compounds may include, for example, BREN-S, EPPN-201, EPPN-501N, EOCN-1020, GAN, and GOT (Nippon Kayaku Co., Ltd.); Adeka Resin EP-4000, Adeka Resin EP-4003S, Adeka Resin EP-4080, Adeka Resin EP-4085, Adeka Resin EP-4088, Adeka Resin EP-4100, Adeka Resin EP-4900, Adeka Resin ED-505, Adeka Resin ED-506, Adeka Resin KRM-2110, Adeka Resin KRM-2199, and Adeka Resin KRM-2720 (Adeka Corporation); R-508, R-531, and R-710 (Mitsui Chemicals); Epicoat 190P, Epicoat 191P, Epicoat 604, Epicoat 801, Epicoat 825, Epicoat 871, Epicoat 872, Epicoat 1031, Epicoat RXE15, Epicoat YX-4000, Epicoat YDE-205
- the functional monomer having at least one ethylenically unsaturated bond is a reactive unsaturated compound and is a monomer or oligomer generally used in a photosensitive resin composition, and monofunctional or polyfunctional esters of acrylic acid or methacrylic acid having at least one ethylenically unsaturated double bond could be used.
- the content of the functional monomer having at least one ethylenically unsaturated bond may be 1 to 50% by weight with respect to the total weight of the photosensitive resin composition excluding the residual amount of solvent. If the content of the functional monomer having at least one ethylenically unsaturated bond is within the above-mentioned range, patterns are formed easily, and it is beneficial in the development margin aspect since overdevelopment of a bottom part is not generated during the developing process.
- the functional monomer having at least one ethylenically unsaturated bond is a reactive unsaturated compound, and examples of the functional monomer having at least one ethylenically unsaturated bond may include at least one selected from the group consisting of ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, 1,6-hexanediol diacrylate, pentaerythritol triacrylate, dipentaerythritol pentacrylate, dipentaerythritol hexacrylate, bisphenol A epoxyacrylate, ethylene glycol monomethylether acrylate, ethylene glycol dimethacrylate and 1,6-hexanediol dimethacrylate, but not limited thereto.
- Examples of commercially available functional monomers having at least one ethylenically unsaturated bond may include the following products: Aronix M-101, Aronix M-111 and Aronix M-114 (Toagosei Co., Ltd.); KAYARAD TC-110S and KAYARAD TC-120S (Nippon Kayaku Co. Ltd.); and V-158 and V-2311 (Osaka Yuki Kagaku Kogyo Kabushiki Kaisha) as commercial products of monofunctional (meth)acrylate;
- Aronix M-210, Aronix M-240 and Aronix M-6200 (Toagosei Co., Ltd.); KAYARAD HDDA, KAYARAD HX-220 and KAYARAD R-604 (Nippon Kayaku Co. Ltd.); and V260, V312 and V335 HP (Osaka Yuki Kagaku Kogyo Kabushiki Kaisha) as commercial products of bifunctional (meth)acrylate products; and
- Aronix M-309, Aronix M-400, Aronix M-405, Aronix M-450, Aronix M-7100, Aronix M-8030 and Aronix M-8060 (Toagosei Co., Ltd.); KAYARAD TMPTA, KAYARAD DPCA-20, KAYARAD DPCA-30, KAYARAD DPCA-60 and KAYARAD DPCA-120 (Nippon Kayaku Co. Ltd.); and V-295, V-300, V-360, V-GPT, V-3PA and V-400 (Osaka Yuki Kagaku Kogyo Kabushiki Kaisha) as commercial products of tri- or higher functional (meth)acrylate products.
- the foregoing compounds can be used alone or in a combination of two or more thereof.
- the content of the functional monomer having at least one ethylenically unsaturated bond is ranged from 1 to 50% by weight, preferably from 1 to 20% by weight, and more preferably from 1 to 15% by weight with respect to the total photosensitive resin composition excluding a residual amount of solvent. If the content of the functional monomer having at least one ethylenically unsaturated bond is within the above-mentioned range of 1 to 50% by weight, sensitivity is improved in the presence of oxygen, patterns are formed easily, compatibility with copolymers is improved, the coat surface is not roughened after the formation of a coat, and it is beneficial in the development margin aspect since overdevelopment of a bottom part is not generated during the development.
- a polymerization initiator in the present invention is a compound which generates active species that are capable of initiating the polymerization of the functional monomer having at least one ethylenically unsaturated bond, or the monofunctional or polyfunctional epoxy compound when exposed to radiation light such as visible rays, ultraviolet rays, far ultraviolet rays, electron rays, and X-rays.
- photopolymerization initiator may include acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, ⁇ -acyloxime based compounds, onium salt-based compounds, benzoin-based compounds, benzophenone-based compounds, dikenone-based compounds, ⁇ -diketone based compounds, polynuclear quinone-based compounds, thioxanthone-based compounds, diazo-based compounds, imidesulfonate-based compounds, oxime-based compounds, carbazole-based compounds, and sulfonium borate-based compounds.
- These compounds are components that generate active radicals, active acids, or both the active radicals and active acids by light exposure, and they may be used alone or in a mixture of two or more thereof.
- acetophenone-based compounds may include 2,2’-diethoxyacetophenone, 2,2’-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, p-t-butyltrichloroacetophenone, p-t-butyldichloroacetophenone, 4-chloroacetophenone, 2,2’-dichloro-4-phenoxyacetophenone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one.
- benzophenone-based compounds may include benzophenone, benzoyl benzoate, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylized benzophenone, 4,4’-bis(dimethylamino)benzophenone, 4,4’-bis(diethylamino)benzophenone, 4,4’-dimethylaminobenzophenone, 4,4’-dichlorobenzophenone, and 3,3’-dimethyl-2-methoxybenzophenone.
- thioxanthone-based compounds may include thioxanthone, 2-crolthioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone.
- benzoin-based compounds may include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.
- triazine-based compounds may include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3’4’-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4’-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho 1-yl)-4,6-bis(trichloromethyl)-
- examples of the polymerization initiator may include one or more selected from the group consisting of p-dimethylaminoacetophenone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, benzyldimethylketal, benzophenone, benzoin propyl ether, diethyl thioxanthone, 2,4-bis(trichloromethyl)-6-p-methoxyphenyl-s-triazine, 2-trichloromethyl-5-styryl-1,3,4-oxodiazole, 9-phenyl acridine, 3-methyl-5-amino-((s-triazine-2-yl)amino)-3-phenylcoumarin, 2-(o-chlorophenyl)-4,5-diphenyl imidazolyl dimer, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime, o-benzoyl-4'-(benzmercap
- the content of the polymerization initiator may be 0.1 to 10% by weight with respect to the total weight of the photosensitive resin composition excluding the residual amount of solvent. If the content of the polymerization initiator is within the above-mentioned range, patterns of a colored layer are easily obtained and the formed colored layer is sufficiently adhered to the substrate during the development since curing due to exposure to light is sufficiently performed.
- the black organic pigment means an organic pigment that has been colorized into black to represent black that is similar to carbon black that is an inorganic pigment.
- black organic pigment may include, but are not limited to, at least one selected from aniline black, lactam black and perylene black.
- the photosensitive resin composition according to the present invention may additionally include a black inorganic pigment along with the black organic pigment, wherein the black inorganic pigment is one or more selected from the group consisting of carbon black, chromium oxide, iron oxide, and titanium black, and its content is from 0.1 to 70 parts by weight with respect to 100 parts by weight of the black organic pigment.
- the black inorganic pigment is one or more selected from the group consisting of carbon black, chromium oxide, iron oxide, and titanium black, and its content is from 0.1 to 70 parts by weight with respect to 100 parts by weight of the black organic pigment.
- the melt flow phenomenon deteriorates, and thus it is difficult to form patterns on a thick film, such as a column spacer. Therefore, it is important to control a mixing ratio of the organic pigment to the inorganic pigment.
- the content of the black organic pigment or both the black organic pigment and the black inorganic pigment may be 10 to 60% by weight with respect to the total weight of the photosensitive resin composition excluding the residual amount of solvent. If the content of the black inorganic pigment is within the above-mentioned range, the optical density is prevented from being too low, and processability, such as developing properties, is improved and high optical densities is achieved.
- a dispersant may be used to disperse a pigment in the photosensitive resin composition according to the present invention.
- the dispersant may be used by adding it to the pigment, for example, by treating the surface of the pigment with the dispersant in advance, or the dispersant may be used by directly adding it along with the pigment when preparing the photosensitive resin composition.
- a solvent used in the present invention has compatibility with the components of the above-mentioned photosensitive resin composition, but does not react with the components.
- the solvent may include compounds comprising: alcohols, such as methanol and ethanol; ethers, such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; glycol ethers, such as ethylene glycol monomethyl ether, and ethylene glycol monoethyl ether; cellosolve acetates, such as methylcellosolve acetate, ethylcellosolve acetate, and diethylcellosolve acetate; carbitols, such as methylethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methylethyl ether, and diethylene glycol diethyl ether; propylene glycol alkylether acetates, such as propylene glycol,
- the examples of the solvent may additionally include high-boiling point solvents, such as N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, benzylethyl ether, dihexyl ether, acetonylacetone, isophorone, capronic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, ⁇ -butyrolactone, ethylene carbonate, propylene carbonate, and phenylcellosolve acetate.
- high-boiling point solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N
- preferable examples of the solvent among the above-mentioned examples may include: glycol esters, such as ethylene glycol monomethyl ether; ethylene glycol alkylether acetates, such as ethyl cellosolve acetate; esters, such as ethyl 2-hydroxy propionate; diethylene glycols, such as diethylene glycol monomethyl ether; and propylene glycol alkylether acetates, such as propylene glycol methylether acetate, and propylene glycol propylether acetate.
- glycol esters such as ethylene glycol monomethyl ether
- ethylene glycol alkylether acetates such as ethyl cellosolve acetate
- esters such as ethyl 2-hydroxy propionate
- diethylene glycols such as diethylene glycol monomethyl ether
- propylene glycol alkylether acetates such as propylene glycol methylether acetate, and propylene glycol propylether
- the solvent is used in a residual amount and preferably contained in an amount of 50 to 90% by weight with respect to the total content 100% by weight of a photosensitive resin composition comprising the solvent.
- the content of the solvent is from 50 to 90% by weight, the resin composition has an appropriate viscosity and processability is improved.
- a photosensitive resin composition of the present invention may further comprise a silane coupling agent having one or more reactive substituents selected from the group consisting of a carboxyl group, a methacryloyl group, an isocyanate group, an epoxy group, and combinations thereof in order to improve adhesive properties to the substrate.
- a silane coupling agent having one or more reactive substituents selected from the group consisting of a carboxyl group, a methacryloyl group, an isocyanate group, an epoxy group, and combinations thereof in order to improve adhesive properties to the substrate.
- silane coupling agent may include trimethoxysilyl benzoic acid, ⁇ -methacryloxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, ⁇ -isocyanatepropyl triethoxysilane, ⁇ -glycidoxy propyl trimethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and they can be used alone or in combination of two or more thereof.
- the addition amount of the silane coupling agent is preferably 0.001 to 20 parts by weight with respect to 100 parts by weight of a photopolymerizable binder resin.
- a photosensitive resin composition of the present invention may additionally include a surfactant, if necessary, in order to improve coatability and prevent the formation of defects.
- surfactant may include fluorine-based surfactants commercialized under the names of: BM-1000 and BM-1100 (BM Chemie); Megaface F142D, F172, F173 and F183 (Dainippon Ink & Chemicals, Inc.); Fluorad FC-135, FC-170C, FC-430 and FC-431 (Sumitomo 3M Co., Ltd.); Surflon S-112, S-113, S-131, S-141 and S-145 (Asahi Glass Co., Ltd.); and SH-28PA, SH-190, SH-193, SZ-6032 and SF-8428 (Toray Dow Corning Silicone).
- fluorine-based surfactants commercialized under the names of: BM-1000 and BM-1100 (BM Chemie); Megaface F142D, F172, F173 and F183 (Dainippon Ink & Chemicals, Inc.); Fluorad FC-135, FC-170C, FC-430 and FC-431 (Sumitomo 3M Co
- the addition amount of the surfactant is preferably 0.001 to 5 parts by weight with respect to 100 parts by weight of the photopolymerizable binder resin.
- the photosensitive resin composition of the present invention may include other additives such as an antioxidant and a stabilizer in certain amounts which do not deteriorate physical properties of the composition.
- the present invention provides a light shielding spacer formed from the photosensitive resin composition.
- the spacer is characterized in that it has a dielectric constant of 8 F/m or less and an optical density of 1.0 or more.
- the present invention provides a liquid crystal display device comprising the spacer.
- the solution was stirred until the solution had an acid value of less than 1.0 mg KOH/g by measuring an acid value of the solution when the solution became transparent and had a high viscosity. It required 11 hours to reach the target acid value of 0.8. After completion of the reaction, the temperature of the reactor was lowered to a room temperature to produce a colorless transparent solid.
- the solution was stirred until the solution had an acid value of less than 1.0 mg KOH/g by measuring an acid value of the solution if the solution became transparent and had a high viscosity. It required 11 hours to reach the target acid value of 0.8. After the completion of the reaction, the temperature of the reactor was lowered to a room temperature to produce a colorless transparent solid.
- the solution was stirred until the solution had an acid value of less than 1.0 mg KOH/g by measuring an acid value of the solution if the solution became transparent and had a high viscosity. It required 11 hours to reach the target acid value of 0.8. After the completion of the reaction, the temperature of the reactor was lowered to a room temperature to produce a colorless transparent solid.
- the reaction product was obtained by addition-reacting compound b-1 that is component (B) with compound a-1 that is component (A) to form an epoxy adduct (AB), and esterifying the epoxy adduct (AB) with compound c-1 that is component (C) in an amount of 0.8 parts by equivalent with respect to 1 part by equivalent of a hydroxyl group of the epoxy adduct (AB), and then additionally esterifying the resulting product with compound d-2 that is component (D) in an amount of 0.3 parts by equivalent of an epoxy group of the compound d-2 with respect to 1 part by equivalent of a hydroxyl group of the epoxy adduct (AB).
- the epoxy adduct (AB) has a structure to which a carboxyl group of compound b-1 is added at a ratio of 1.0 with respect to an epoxy group of compound a-1.
- the reaction product was obtained by addition-reacting compound b-1 that is component (B) with compound a-2 that is component (A) to form an epoxy adduct (AB), and esterifying the epoxy adduct (AB) with compound c-2 that is component (C) in an amount of 0.8 parts by equivalent with respect to 1 part by equivalent of a hydroxyl group of the epoxy adduct (AB).
- the epoxy adduct (AB) has a structure to which a carboxyl group of compound b-1 is added at a ratio of 1.0 with respect to an epoxy group of compound a-2.
- the reaction product was obtained by addition-reacting compound b-1 that is component (B) with compound a-3 that is component (A) to form an epoxy adduct (AB), and esterifying the epoxy adduct (AB) with compound c-2 that is component (C) in an amount of 0.8 parts by equivalent with respect to 1 part by equivalent of a hydroxyl group of the epoxy adduct (AB).
- the epoxy adduct (AB) has a structure to which a carboxyl group of compound b-1 is added at a ratio of 1.0 with respect to an epoxy group of compound a-2.
- a pigment composition was prepared using the same method as in Preparation Example 4, except that 35 parts by weight of lactam black and 15 parts by weight of carbon black produced by Degussa were used, instead of 50 parts by weight of lactam black in Preparation Example 4.
- a pigment composition was prepared using the same method as in Preparation Example 4, except that 30 parts by weight of lactam black and 20 parts by weight of carbon black produced by Degussa were used, instead of 50 parts by weight of lactam black in Preparation Example 4.
- a pigment composition was prepared using the same method as in Preparation Example 4, except that 25 parts by weight of lactam black and 25 parts by weight of carbon black produced by Degussa were used, instead of 50 parts by weight of lactam black in Preparation Example 4.
- a pigment composition was prepared using the same method as in Preparation Example 4, except that 15 parts by weight of lactam black and 35 parts by weight of carbon black produced by Degussa were used, instead of 50 parts by weight of lactam black in Preparation Example 4.
- a pigment composition was prepared in the same method as in Preparation Example 4 except that 50 parts by weight of carbon black produced by Degussa were used instead of 50 parts by weight of lactam black in the Preparation Example 4.
- a photosensitive resin composition having black alkali developing properties was obtained by well stirring 1.7538 g of a bisphenol type binder (ZFR-2041H, Nippon Kayaku Co., Ltd.), 0.7249 g of dipentaerythritol hexaacrylate, 0.0651 g of an oxime-based photoinitiator (OXE-02, Ciba-Geigy Corporation), 0.0042 g of a leveling surfactant (silicone-based surfactant BYK 333, produced by BYK Corporation), 0.0084 g of an adhesion assisting agent (KBE-9007, Shin-Etsu Chemical Co., Ltd.), and 8.9 g of a black organic pigment and inorganic pigment composition obtained in Preparation Example 6 in 8.543 g of propylene glycol-1-monomethyl ether-2-acetate.
- a photosensitive resin composition having black alkali developing properties was obtained by well stirring 2.398 g of Cardo type binder (CBR-D07-3, Kyungin Synthetic Corporation), 0.7249 g of dipentaerythritol hexaacrylate, 0.0651 g of an oxime-based photoinitiator (OXE-02, Ciba-Geigy Corporation), 0.0042 g of a leveling surfactant (silicone-based surfactant BYK 333, BYK Corporation), 0.0084 g of an adhesion assisting agent (KBE-9007, Shin-Etsu Chemical Co., Ltd.), and 8.9 g of a black organic pigment and inorganic pigment composition obtained in Preparation Example 6 in 7.6188 g of propylene glycol-1-monomethyl ether-2-acetate.
- a film was formed by coating a photosensitive resin composition of the present invention on a pre-treated substrate to a desired thickness, e.g., a thickness of 2 to 25 ⁇ m by a conventional coating method such as a spin or slit coating method, a roll coating method, a screen printing method and an applicator method, and heating the coating at a temperature of 70 to 90°C for 1 to 10 minutes to remove the solvent.
- a desired thickness e.g., a thickness of 2 to 25 ⁇ m by a conventional coating method such as a spin or slit coating method, a roll coating method, a screen printing method and an applicator method, and heating the coating at a temperature of 70 to 90°C for 1 to 10 minutes to remove the solvent.
- An active ray of 200 to 500 nm was irradiated through a mask of a predetermined shape to form required patterns on the obtained film.
- Examples of light sources used for irradiation may include a low pressure mercury lamp, a high pressure mercury lamp, an ultra-high pressure mercury lamp, a metal halide lamp, and an argon gas laser, and may additionally include X-rays and electron rays, if necessary.
- the amount of light exposure varies depending on types and mixing amounts of respective components, and the thickness of a dried film, it is not more than 500 mJ/cm 2 (when measured by a 365 nm sensor) in the case of using the high pressure mercury lamp.
- patterns were formed by dissolving and removing unnecessary parts using an aqueous alkali solution as a developer, thereby allowing only light-exposed parts to remain.
- the image patterns obtained by the development were cooled to room temperature, and post-baked at 230°C in a hot-air circulation type drying furnace for 20 minutes to produce image patterns.
- the resolution of the obtained image patterns was measured by observing minimum sizes of formed colored spacers using a micro-optical microscope.
- Absorbance is the amount of light when the luminous intensity of light becomes constant after the light of a certain wavelength passes through a certain layer, and optical density is obtained by dividing the absorbance value by thickness.
- the optical density is defined as log 10 (I 0 /I). Luminous intensity of light in a specific wavelength band was measured using an optical density meter (361T Tabletop Transmission Densitometer manufactured by X-Lite Corporation).
- colored spacers having a thicknesses (T) of 3.7 ( ⁇ 0.2) ⁇ m and a width (W) of 35 ( ⁇ 2) ⁇ m were prepared.
- the compression displacement and elastic recovery ratio of the colored spacers were measured according to the following methods using an elasticity measurement apparatus (DUH-W201S) manufactured by Shimadzu Corporation in Japan.
- a flat-surfaced perpetrator with a diameter of 50 ⁇ m was used as a penetrator for pressing the patterns, and the measuring principle used a load-unload method. Loads given in the tests were 300 mN and 400 mN. The loading rate and holding time were constantly maintained at 0.45 gf/sec and 3 seconds, respectively. The elastic recovery ratio was obtained by measuring the thicknesses of the patterns after a loading and unloading with the flat-surfaced perpetrator for 3 seconds using a three-dimensional thickness measurement apparatus.
- the elastic recovery ratio means the ratio of a recovered distance (D 1 -D 2 ) after a recovery time of 10 minutes to a distance (D 1 ) of the pattern that is indented when a loading is given to the pattern, and is represented by the following Equation 1:
- D 1 ( ⁇ m) is a compressed displacement
- D 2 ( ⁇ m) a distance of the pattern that is indented after the recovery time
- Films having final thicknesses ranging from 1.5 to 2.5 ⁇ m were prepared by coating photoresists (PR) formed from the black photosensitive resin compositions prepared in the Examples and Comparative Examples on an indium tin oxide (ITO) glass and drying the coated photoresists (PR) on a hot plate under a temperature of 90°C for 2.5 minutes.
- a gold (Au) electrode with a diameter of 300 ⁇ m was deposited on the films to prepare samples.
- Capacitance values were measured using an HP 4294A Precision Impedance Analyzer, and dielectric constants were obtained using the measured capacitance values and the following Equation 2.
- C indicates an electric capacitance
- ⁇ 0 indicates a dielectric constant in a vacuum condition
- ⁇ indicates a relative dielectric constant of the film
- A indicates an electrode area
- d indicates a photoresist (PR) thickness.
- ⁇ dielectric constant
- ⁇ dielectric constant
- the subject photosensitive resin compositions of Examples 1 to 6 are uniformly excellent in optical density, dielectric constant, elastic recovery ratio, and resolution.
- Examples 1 to 5 were superior to Comparative Examples 1 and 2 in the resolution aspect, were superior to Comparative Examples 3, 4 and 5 in the dielectric constant aspect, and were superior to Comparative Examples 1 to 5 in the aspect of 300 mN and 400 mN elastic recovery ratios.
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Abstract
La présente invention concerne une résine insaturée photopolymérisable, une composition de résine photosensible comprenant ladite résine insaturée photopolymérisable, un monomère fonctionnel comportant au moins une liaison éthyléniquement insaturée, un initiateur de polymérisation, un pigment organique noir et un solvant. La composition de résine photosensible est utile pour préparer un espaceur protégeant de la lumière ayant une faible constante diélectrique et d'excellentes propriétés de protection de la lumière, une excellente résolution et un excellent rapport de recouvrance élastique.
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JP2014527083A JP6093766B2 (ja) | 2011-08-26 | 2012-08-24 | 光重合性不飽和樹脂、これを含む感光性樹脂組成物、並びにそれから形成された光遮蔽スペーサーおよび液晶ディスプレイデバイス |
CN201280052030.6A CN103890659A (zh) | 2011-08-26 | 2012-08-24 | 光可聚合不饱和树脂,含有该光可聚合不饱和树脂的光敏树脂组合物,以及由此制备的光屏蔽间隔和液晶显示器件 |
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KR1020110086025A KR101349622B1 (ko) | 2011-08-26 | 2011-08-26 | 광중합성 불포화 수지, 이를 포함하는 감광성 수지 조성물 및 이로부터 형성되는 차광성 스페이서와 액정 디스플레이 장치 |
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2011
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2012
- 2012-08-24 TW TW101130773A patent/TWI477526B/zh active
- 2012-08-24 CN CN201280052030.6A patent/CN103890659A/zh active Pending
- 2012-08-24 WO PCT/KR2012/006802 patent/WO2013032190A1/fr active Application Filing
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- 2012-08-24 CN CN201910295325.XA patent/CN110007562A/zh not_active Withdrawn
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KR20200021043A (ko) | 2017-06-20 | 2020-02-27 | 가부시키가이샤 아데카 | 중합성 조성물, 블랙 매트릭스용 감광성 조성물 및 블랙 칼럼 스페이서용 감광성 조성물 |
Also Published As
Publication number | Publication date |
---|---|
KR101349622B1 (ko) | 2014-01-10 |
KR20130022955A (ko) | 2013-03-07 |
JP6093766B2 (ja) | 2017-03-08 |
TW201326244A (zh) | 2013-07-01 |
CN110007562A (zh) | 2019-07-12 |
TWI477526B (zh) | 2015-03-21 |
JP2014529652A (ja) | 2014-11-13 |
CN103890659A (zh) | 2014-06-25 |
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