JPWO2004104683A1 - 液晶シール剤およびそれを用いた液晶表示セル - Google Patents
液晶シール剤およびそれを用いた液晶表示セル Download PDFInfo
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- JPWO2004104683A1 JPWO2004104683A1 JP2005506333A JP2005506333A JPWO2004104683A1 JP WO2004104683 A1 JPWO2004104683 A1 JP WO2004104683A1 JP 2005506333 A JP2005506333 A JP 2005506333A JP 2005506333 A JP2005506333 A JP 2005506333A JP WO2004104683 A1 JPWO2004104683 A1 JP WO2004104683A1
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- Prior art keywords
- liquid crystal
- crystal sealant
- agent
- weight
- radiation curable
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 203
- 239000000565 sealant Substances 0.000 title claims abstract description 80
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 48
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 31
- 239000002245 particle Substances 0.000 claims abstract description 29
- 239000003999 initiator Substances 0.000 claims abstract description 28
- 230000005855 radiation Effects 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 239000011256 inorganic filler Substances 0.000 claims abstract description 11
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 239000003822 epoxy resin Substances 0.000 claims description 31
- 229920000647 polyepoxide Polymers 0.000 claims description 31
- 238000007789 sealing Methods 0.000 claims description 31
- 239000000758 substrate Substances 0.000 claims description 25
- 229920001187 thermosetting polymer Polymers 0.000 claims description 16
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 9
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 claims description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 5
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 4
- 239000004474 valine Substances 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000011109 contamination Methods 0.000 abstract description 18
- 239000007788 liquid Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 description 28
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 16
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 14
- 238000001723 curing Methods 0.000 description 14
- 239000004593 Epoxy Substances 0.000 description 12
- 239000000853 adhesive Substances 0.000 description 11
- 230000001070 adhesive effect Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- AGXAFZNONAXBOS-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethyl)phenyl]methyl]oxirane Chemical compound C=1C=CC(CC2OC2)=CC=1CC1CO1 AGXAFZNONAXBOS-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 238000000016 photochemical curing Methods 0.000 description 8
- 150000003254 radicals Chemical group 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 6
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- DCBJXJOKADGNAA-UHFFFAOYSA-N 2-methyl-1-[6-(2-methyl-2-morpholin-4-ylpropanoyl)-9-octylcarbazol-3-yl]-2-morpholin-4-ylpropan-1-one Chemical compound C=1C=C2N(CCCCCCCC)C3=CC=C(C(=O)C(C)(C)N4CCOCC4)C=C3C2=CC=1C(=O)C(C)(C)N1CCOCC1 DCBJXJOKADGNAA-UHFFFAOYSA-N 0.000 description 4
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- -1 benzyl dimethyl ketal Chemical compound 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000012792 core layer Substances 0.000 description 4
- 239000011258 core-shell material Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
- 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 4
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 3
- 238000010538 cationic polymerization reaction Methods 0.000 description 3
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000005350 fused silica glass Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000013007 heat curing Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 229960001755 resorcinol Drugs 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- 0 CCC(O)OCC(COc1cc(OCC(*)COC2CC=CC(COCC(COC(C=C)O)O)C2)ccc1)O Chemical compound CCC(O)OCC(COc1cc(OCC(*)COC2CC=CC(COCC(COC(C=C)O)O)C2)ccc1)O 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 238000007718 adhesive strength test Methods 0.000 description 2
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- 230000007547 defect Effects 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
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- 230000007062 hydrolysis Effects 0.000 description 2
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
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- 239000012766 organic filler Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
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- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 2
- ZNGSVRYVWHOWLX-KHFUBBAMSA-N (1r,2s)-2-(methylamino)-1-phenylpropan-1-ol;hydrate Chemical compound O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 ZNGSVRYVWHOWLX-KHFUBBAMSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- SNVRDQORMVVQBI-OWOJBTEDSA-N (e)-but-2-enedihydrazide Chemical compound NNC(=O)\C=C\C(=O)NN SNVRDQORMVVQBI-OWOJBTEDSA-N 0.000 description 1
- SNVRDQORMVVQBI-UPHRSURJSA-N (z)-but-2-enedihydrazide Chemical compound NNC(=O)\C=C/C(=O)NN SNVRDQORMVVQBI-UPHRSURJSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- NKANYVMWDXJHLE-UHFFFAOYSA-N 2-[[2-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1OCC1CO1 NKANYVMWDXJHLE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FSYPIGPPWAJCJG-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1CO1 FSYPIGPPWAJCJG-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- RLTACIWKRKVZKZ-UHFFFAOYSA-N O=S(c(cc1)ccc1OCC1OC1)(c(cc1)ccc1OCC1OC1)=O Chemical compound O=S(c(cc1)ccc1OCC1OC1)(c(cc1)ccc1OCC1OC1)=O RLTACIWKRKVZKZ-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- GPBKPJXNAVXOJU-UHFFFAOYSA-N benzene-1,2,4-tricarbohydrazide Chemical compound NNC(=O)C1=CC=C(C(=O)NN)C(C(=O)NN)=C1 GPBKPJXNAVXOJU-UHFFFAOYSA-N 0.000 description 1
- ALHNLFMSAXZKRC-UHFFFAOYSA-N benzene-1,4-dicarbohydrazide Chemical compound NNC(=O)C1=CC=C(C(=O)NN)C=C1 ALHNLFMSAXZKRC-UHFFFAOYSA-N 0.000 description 1
- ICQFAQGXJAVDED-UHFFFAOYSA-N benzene-1,4-diol;4-(methylamino)phenol Chemical compound OC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ICQFAQGXJAVDED-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- UHVCSNKHFBQKBO-UHFFFAOYSA-N benzyl-ethenyl-[2-(3-trimethoxysilylpropylamino)ethyl]azanium;chloride Chemical compound Cl.CO[Si](OC)(OC)CCCNCCN(C=C)CC1=CC=CC=C1 UHVCSNKHFBQKBO-UHFFFAOYSA-N 0.000 description 1
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- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 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
- 238000010438 heat treatment Methods 0.000 description 1
- OXAGUPFRAIIDLT-UHFFFAOYSA-N heptanedihydrazide Chemical compound NNC(=O)CCCCCC(=O)NN OXAGUPFRAIIDLT-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- IFZUFHWISBKFJP-UHFFFAOYSA-N n'-[4-[dimethoxy(methyl)silyl]oxybutyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)OCCCCNCCN IFZUFHWISBKFJP-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- ZWLFGLCGZUVIEA-UHFFFAOYSA-N nonanedihydrazide Chemical compound NNC(=O)CCCCCCCC(=O)NN ZWLFGLCGZUVIEA-UHFFFAOYSA-N 0.000 description 1
- HATIEXJZXOLRAO-UHFFFAOYSA-N octanedihydrazide Chemical compound NNC(=O)CCCCCCC(=O)NN HATIEXJZXOLRAO-UHFFFAOYSA-N 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
(1)(a)一般式(1)で表される放射線硬化樹脂、(b)光重合開始剤、及び(c)平均粒径3μm以下の無機充填材を必須成分として含有することを特徴とする液晶シール剤、
(2)(a)放射線硬化樹脂が一般式(2)で表される放射線硬化樹脂である、(1)に記載の液晶シール剤、
(3)(a)放射線硬化樹脂の含有量が液晶シール剤全体に対して30重量%〜80重量%である、(1)又は(2)に記載の液晶シール剤、
(4)(a)放射線硬化樹脂の粘度が30〜500Pa・sである(1)乃至(3)の何れか1項に記載の液晶シール剤、
(5)(b)光重合開始剤がラジカル型光重合開始剤である(1)乃至(4)の何れか1項に記載の液晶シール剤、
(6)(b)ラジカル型光重合開始剤がカルバゾール系開始剤である(5)に記載の液晶シール剤、
(7)更に(d)エポキシ樹脂及び(e)熱硬化剤を含有する(1)乃至(6)の何れか1項に記載の液晶シール剤、
(8)(d)エポキシ樹脂が、該エポキシ樹脂を10倍量の液晶と直接接触させ120℃で1時間静置した場合に、液晶に対して0.5重量%以上溶出しないエポキシ樹脂である(7)に記載の液晶シール剤、
(9)(e)熱硬化剤がジヒドラジド類である(7)又は(8)に記載の液晶シール剤、
(10)ジヒドラジド類がイソフタル酸ジヒドラジド及び/又はバリンヒダントイン骨格を有するジヒドラジド類である(9)に記載の液晶シール剤、
(11)(e)熱硬化剤が多価フェノール類である(7)又は(8)に記載の液晶シール剤、
(12)更に(f)シランカップリング剤を含有する(1)乃至(11)の何れか1項に記載の液晶シール剤、
(13)シランカップリング剤がアミノ基を有するシランカップリング剤である(12)に記載の液晶シール剤、
(14)(1)乃至(13)の何れか1項に記載の液晶シール剤の硬化物でシールされた液晶表示セル、及び
(15)一方の基板に形成された(1)乃至(13)の何れか1項に記載の液晶シール剤の内側に液晶を滴下した後、もう一方の基板を貼り合わせることを特徴とする液晶表示セルの製造方法、に関する。
レゾルシンジグリシジルエーテル樹脂をトルエンに溶解し、これに重合禁止剤としてジブチルヒドロキシトルエンを加え、60℃まで昇温した。その後、エポキシ基の100%当量のアクリル酸を加え更に80℃まで昇温し、これに反応触媒であるトリメチルアンモニウムクロライドを添加して、98℃で約50時間攪拌した。得られた反応液を水洗し、トルエンを留去することにより、目的とするレゾルシンのエポキシアクリレートを得た。(エポキシアクリレートA)
ビスフェノールFエポキシ樹脂(日本化薬株式会社製、RE−404P、エポキシ当量160g/eq、加水分解量30ppm)をトルエンに溶解し、これに重合禁止剤としてジブチルヒドロキシトルエンを加え、60℃まで昇温した。その後、エポキシ基の60%当量のアクリル酸を加え更に80℃まで昇温し、これに反応触媒であるトリメチルアンモニウムクロライドを添加して、98℃で約50時間攪拌した。得られた反応液を水洗し、トルエンを留去することにより、目的とするビスフェノールFの部分エポキシアクリレートを得た(エポキシアクリレートC)。
前記合成したエポキシアクリレートA〜Cをそれぞれサンプル管に0.1g入れ、液晶(メルク製、MLC−6866−100)を加えて直接接触させ、120℃オーブンに1時間投入し、その後0.5時間室温にて放置した。液晶のみを取り出した後、この液晶に溶出した成分を、ペンタデカンを内部標準物質に用い、ガスクロマトグラフィーにて定量した。表1に溶出物の量を液晶に対しての重量%で表した。レゾルシンジグリシジルエーテルのエポキシアクリレート(エポキシアクリレートA)は低粘度であるにも拘らず、ビスフェノールFエポキシの100%エポキシアクリレート(エポキシアクリレートB)と比較して約1/3程度の溶出しかない。ビスフェノールFエポキシの60%部分エポキシアクリレート体(エポキシアクリレートC)は両端のエポキシ基がアクリル化されたもの、片側のみがアクリル化されたモノアクリル化体、原料となるエポキシ樹脂の3種の溶出が確認された。このようにレゾルシンジグリシジルエーテルのエポキシアクリレート(エポキシアクリレートA)は他のエポキシアクリレートと比較して液晶への溶出が少ないことが分かる。
合成例2のエポキシアクリレートBを70重量部、エポキシ樹脂としてEBPS−300(日本化薬株式会社製;エポキシ当量233g/eq、ビスフェノールS型エポキシ樹脂)20重量部、反応性希釈剤としてジペンタエリスリトール・カプロラクトンとアクリル酸の反応物(日本化薬製、DPCA−60、6官能)10重量部、ラジカル発生型光重合開始剤として3,6−ビス(2−メチル−2−モルホリノプロピオニル)−9−n−オクチルカルバゾール(旭電化工業製、アデカオプトマーN−1414)1.8重量部、アミノシランカップリング剤(N−β(アミノエチル)γ−アミノプロピルトリメトキシシラン、信越シリコーン製、KBM−603)1.2重量部を90℃で加熱溶解し、樹脂液を得た。室温に冷却後、イソフタル酸ジヒドラジド(商品名IDH−S;大塚化学株式会社製ジェットミル粉砕グレードを更にジェットミルで微粉砕したもの、融点224℃、活性水素当量48.5g/eq、平均粒径1.7μm、最大粒径7μm)5重量部、アルミナ(シーアイ化成株式会社製、SPC−Al、平均粒径1.0μm)30重量部、コアシェルゴム微粒子:パラロイドEXL−2655(呉羽化学工業株式会社製、コア層:架橋ポリブタジエン、シェル層:メタクリル酸アルキル−スチレン共重合物、平均粒子径200nm)7重量部を添加して、3本ロールにより混練して本発明の液晶シール剤を得た。液晶シール剤の粘度(25℃)は400Pa・sであった(R型粘度計(東機産業株式会社製))
合成例3のエポキシアクリレートCを100重量部、ラジカル発生型光重合開始剤として3,6−ビス(2−メチル−2−モルホリノプロピオニル)−9−n−オクチルカルバゾール(旭電化工業製、アデカオプトマーN−1414)1.8重量部、アミノシランカップリング剤(N−β(アミノエチル)γ−アミノプロピルトリメトキシシラン、信越シリコーン製、KBM−603)1.2重量部を90℃で加熱溶解し、樹脂液を得た。室温に冷却後、イソフタル酸ジヒドラジド(商品名IDH−S;大塚化学株式会社製ジェットミル粉砕グレードを更にジェットミルで微粉砕したもの、融点224℃、活性水素当量48.5g/eq、平均粒径1.7μm、最大粒径7μm)5重量部、アルミナ(シーアイ化成株式会社製、SPC−Al、平均粒径1.0μm)30重量部、コアシェルゴム微粒子:パラロイドEXL−2655(呉羽化学工業株式会社製、コア層:架橋ポリブタジエン、シェル層:メタクリル酸アルキル−スチレン共重合物、平均粒子径200nm)7重量部を添加して、3本ロールにより混練して本発明の液晶シール剤を得た。液晶シール剤の粘度(25℃)は200Pa・sであった(R型粘度計(東機産業株式会社製))
次に、実施例1、2及び比較例1、2の液晶シール剤について、液晶汚染性テスト(UV+熱)、接着強度テスト、ガラス転移点を測定した。
液晶に対する汚染性の指標として、以下の通り接触液晶の比抵抗の測定を行った。
得られた液晶シール剤100gにスペーサーとして5μmのグラスファイバー1gを添加して混合撹拌を行った。この液晶シール剤を50mm×50mmのガラス基板上に塗布し、その液晶シール剤上に1.5mm×1.5mmのガラス片を貼り合わせUV照射機により2000mJ/cm2の紫外線を照射した後、120℃オーブンに1時間投入して硬化させた。そのガラス片のせん断接着強度を測定した。その結果を表2に示した。
得られた液晶シール剤をポリエチレンテレフタレート(PET)フィルムに挟み厚み100μmの薄膜としたものにUV照射機により2000mJ/cm2の紫外線を照射した後、120℃オーブンに1時間投入して硬化させ、硬化後PETフィルムを剥がしてサンプルとした。TMA試験機(真空理工株式会社製)引っ張りモードにてガラス転移点を測定した。その結果を表2に示した。
Claims (15)
- (a)放射線硬化樹脂の含有量が液晶シール剤全体に対して30重量%〜80重量%である、請求項1又は2に記載の液晶シール剤。
- (a)放射線硬化樹脂の粘度が30〜500Pa・sである請求項1乃至3の何れか1項に記載の液晶シール剤。
- (b)光重合開始剤がラジカル型光重合開始剤である請求項1乃至4の何れか1項に記載の液晶シール剤。
- (b)ラジカル型光重合開始剤がカルバゾール系開始剤である請求項5に記載の液晶シール剤。
- 更に(d)エポキシ樹脂及び(e)熱硬化剤を含有する請求項1乃至6の何れか1項に記載の液晶シール剤。
- (d)エポキシ樹脂が、該エポキシ樹脂を10倍量の液晶と直接接触させ120℃で1時間静置した場合に、液晶に対して0.5重量%以上溶出しないエポキシ樹脂である請求項7に記載の液晶シール剤。
- (e)熱硬化剤がジヒドラジド類である請求項7又は8に記載の液晶シール剤。
- ジヒドラジド類がイソフタル酸ジヒドラジド及び/又はバリンヒダントイン骨格を有するジヒドラジド類である請求項9に記載の液晶シール剤。
- (e)熱硬化剤が多価フェノール類である請求項7又は8に記載の液晶シール剤。
- 更に(f)シランカップリング剤を含有する請求項1乃至11の何れか1項に記載の液晶シール剤。
- シランカップリング剤がアミノ基を有するシランカップリング剤である請求項12に記載の液晶シール剤。
- 請求項1乃至13の何れか1項に記載の液晶シール剤の硬化物でシールされた液晶表示セル。
- 一方の基板に形成された請求項1乃至13の何れか1項に記載の液晶シール剤の内側に液晶を滴下した後、もう一方の基板を貼り合わせることを特徴とする液晶表示セルの製造方法。
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PCT/JP2004/006646 WO2004104683A1 (ja) | 2003-05-21 | 2004-05-18 | 液晶シール剤およびそれを用いた液晶表示セル |
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JP (1) | JP3921493B2 (ja) |
KR (2) | KR101194558B1 (ja) |
CA (1) | CA2525178A1 (ja) |
DE (1) | DE602004021928D1 (ja) |
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Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101189591B1 (ko) * | 2004-10-20 | 2012-10-12 | 니폰 가야꾸 가부시끼가이샤 | 방사선 경화성 수지, 액정 실링제 및 이것을 사용한 액정표시 셀 |
WO2006073053A1 (ja) * | 2005-01-06 | 2006-07-13 | Nippon Kayaku Kabushiki Kaisha | 液晶シール剤及びそれを用いた液晶表示セル |
JP5074699B2 (ja) * | 2005-03-25 | 2012-11-14 | 積水化学工業株式会社 | 液晶滴下工法用シール剤、上下導通材料及び液晶表示素子 |
JP5368666B2 (ja) * | 2005-05-09 | 2013-12-18 | 積水化学工業株式会社 | 液晶表示素子の製造方法 |
EP1932894A1 (en) * | 2005-09-02 | 2008-06-18 | Dainippon Ink And Chemicals, Inc. | Photocurable composition for sealing agent, liquid crystal sealing agent, and liquid crystal panel |
KR100722813B1 (ko) | 2005-12-30 | 2007-05-30 | (주)디피아이 홀딩스 | 실란트 조성물 및 이를 이용한 접착 방법 |
CN101416104B (zh) * | 2006-03-29 | 2011-05-25 | 积水化学工业株式会社 | 液晶滴下技术用密封剂、上下导通材料及液晶显示元件 |
JP2007326933A (ja) * | 2006-06-07 | 2007-12-20 | Dainippon Ink & Chem Inc | エポキシビニルエステル樹脂、その製造法、感光性樹脂組成物、その硬化物、酸ペンダント型エポキシビニルエステル樹脂、アルカリ現像性感光性樹脂組成物、及びその硬化物 |
JP4974344B2 (ja) * | 2006-06-19 | 2012-07-11 | 日本化薬株式会社 | 液晶シール剤及びそれを用いた液晶表示セル |
US7982322B2 (en) * | 2006-10-06 | 2011-07-19 | Hitachi Chemical Co., Ltd. | Liquid resin composition for electronic part sealing, and electronic part apparatus utilizing the same |
DE102008000721A1 (de) * | 2008-03-18 | 2009-09-24 | Evonik Degussa Gmbh | Strahlenhärtbare Formulierungen |
KR101490484B1 (ko) * | 2008-09-26 | 2015-02-05 | 삼성디스플레이 주식회사 | 액정 표시 장치 및 그 제조 방법 |
KR101220047B1 (ko) * | 2009-10-12 | 2013-01-08 | 금호석유화학 주식회사 | 액정 표시 소자용 실란트 조성물 |
JP5374324B2 (ja) * | 2009-11-12 | 2013-12-25 | 積水化学工業株式会社 | 液晶滴下工法用シール剤、上下導通材料、及び、液晶表示素子 |
JP5605827B2 (ja) * | 2010-01-07 | 2014-10-15 | 株式会社カネカ | 不飽和エステル系樹脂組成物、不飽和エステル系硬化物、及びこれらの製造方法 |
JP5564028B2 (ja) * | 2011-11-07 | 2014-07-30 | 積水化学工業株式会社 | 液晶滴下工法用シール剤、上下導通材料及び液晶表示素子 |
TWI545155B (zh) * | 2012-06-05 | 2016-08-11 | 三菱麗陽股份有限公司 | 環氧樹脂組成物、預浸絲束、複合材料補強壓力容器以及鋼腱 |
KR20140074710A (ko) | 2012-12-10 | 2014-06-18 | 삼성디스플레이 주식회사 | 표시 장치 및 그 제조 방법 |
US10053597B2 (en) | 2013-01-18 | 2018-08-21 | Basf Se | Acrylic dispersion-based coating compositions |
CN103205216B (zh) * | 2013-03-25 | 2015-10-14 | 北京京东方光电科技有限公司 | 封框胶及其制备方法 |
WO2016090182A1 (en) * | 2014-12-03 | 2016-06-09 | Fox Broadcasting Company | Location agnostic media control room and broadcasting facility |
CN105743670B (zh) * | 2014-12-09 | 2019-02-05 | 华为技术有限公司 | 访问控制方法、系统和接入点 |
JP2018533072A (ja) | 2015-10-23 | 2018-11-08 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | ベンジルモノケタール類およびそれらの使用 |
WO2019230709A1 (ja) * | 2018-06-01 | 2019-12-05 | 積水化学工業株式会社 | 液晶表示素子用シール剤、上下導通材料、及び、液晶表示素子 |
Family Cites Families (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2965610A (en) * | 1958-06-30 | 1960-12-20 | Shell Oil Co | Process for curing polyepoxides and resulting products |
US3144421A (en) * | 1961-04-11 | 1964-08-11 | Weyerhaeuser Co | Epoxy molding compound including a high molecular weight saturated fatty acid |
US3294748A (en) * | 1962-05-23 | 1966-12-27 | Westinghouse Electric Corp | Curing agents for epoxy resins |
US3450613A (en) * | 1964-03-09 | 1969-06-17 | Bausch & Lomb | Epoxy adhesive containing acrylic acid-epoxy reaction products and photosensitizers |
US3901833A (en) * | 1970-10-23 | 1975-08-26 | Ciba Geigy Corp | Hardenable epoxy resin compositions and process for making the same |
US3853962A (en) * | 1972-02-03 | 1974-12-10 | Johnson & Johnson | Novel methacrylate monomer |
US3840448A (en) * | 1972-06-26 | 1974-10-08 | Union Carbide Corp | Surface curing of acrylyl or methacrylyl compounds using radiation of 2,537 angstroms |
US4133780A (en) * | 1975-09-04 | 1979-01-09 | Basf Wyandotte Corporation | Polyurethane foams prepared from condensation products of amines, epihalohydrins and alkylene oxides |
GB1587536A (en) * | 1977-07-05 | 1981-04-08 | Ciba Geigy Ag | Expoxide resin-impregnated composites |
US4297401A (en) * | 1978-12-26 | 1981-10-27 | Minnesota Mining & Manufacturing Company | Liquid crystal display and photopolymerizable sealant therefor |
US4526940A (en) * | 1982-06-07 | 1985-07-02 | Ciba-Geigy Corporation | Hydroxyl terminated polyfunctional epoxy curing agents |
JPS59137929A (ja) * | 1983-01-28 | 1984-08-08 | Matsushita Electric Ind Co Ltd | 液晶表示パネル用シ−ル材料 |
JPS6289930A (ja) * | 1985-10-12 | 1987-04-24 | Nippon Soda Co Ltd | 液晶セルの製造方法 |
JPH0820627B2 (ja) | 1987-01-20 | 1996-03-04 | 松下電器産業株式会社 | 液晶表示素子の製造法 |
JPH0823691B2 (ja) * | 1989-02-24 | 1996-03-06 | 日本合成化学工業株式会社 | 感光性樹脂組成物 |
JPH05262850A (ja) | 1992-03-18 | 1993-10-12 | Nippon Kayaku Co Ltd | 液晶セル用シール剤組成物及び液晶表示素子 |
JPH05279451A (ja) * | 1992-03-31 | 1993-10-26 | Nippon Kayaku Co Ltd | エポキシ樹脂組成物及びその硬化物 |
JP3162179B2 (ja) | 1992-04-17 | 2001-04-25 | 協立化学産業株式会社 | 液晶表示装置の枠シール剤組成物 |
JP3200481B2 (ja) * | 1992-11-18 | 2001-08-20 | ナミックス株式会社 | 液晶表示パネル用シール材及びそれを用いた液晶表示パネル |
JPH07168193A (ja) | 1993-09-02 | 1995-07-04 | Loctite Ireland Ltd | 液晶ディスプレーの製造方法およびこの方法に使用する組成物 |
JP2846842B2 (ja) | 1995-06-22 | 1999-01-13 | 松下電器産業株式会社 | 液晶シール材及び液晶表示装置 |
US5889076A (en) | 1996-04-08 | 1999-03-30 | Henkel Corporation | Radiation curable rheology modifiers |
JPH09286078A (ja) * | 1996-04-23 | 1997-11-04 | Kureha Chem Ind Co Ltd | 多層フイルム |
JP3234496B2 (ja) | 1996-05-21 | 2001-12-04 | 松下電器産業株式会社 | 液晶表示装置の製造方法 |
JPH10239694A (ja) | 1997-02-24 | 1998-09-11 | Hitachi Ltd | 液晶表示装置の製造方法 |
US6156816A (en) * | 1998-08-20 | 2000-12-05 | Henkel Corporation | Screen coating composition and method for applying same |
WO2000060005A1 (fr) * | 1999-04-01 | 2000-10-12 | Mitsui Chemicals, Inc. | Enduit d'etancheite pour affichages a cristaux liquides |
US6656979B1 (en) * | 1999-05-20 | 2003-12-02 | 3M Innovative Properties Company | Adhesive/sealant composition and bonded structure using the same |
WO2000078887A1 (fr) * | 1999-06-18 | 2000-12-28 | Hitachi Chemical Company, Ltd. | Adhesif, element adhesif, substrat de circuit pour montage de semi-conducteur presentant un element adhesif, et dispositif a semi-conducteur contenant ce dernier |
JP3583326B2 (ja) | 1999-11-01 | 2004-11-04 | 協立化学産業株式会社 | Lcdパネルの滴下工法用シール剤 |
JP2001152109A (ja) * | 1999-11-29 | 2001-06-05 | Nitto Denko Corp | 感圧性接着剤組成物および感圧性接着テープ類 |
KR100711423B1 (ko) * | 2000-03-14 | 2007-05-02 | 린텍 가부시키가이샤 | 점착제 조성물, 그것을 사용한 점착시트 및 점착성 광학부재 |
JP2001311953A (ja) * | 2000-04-28 | 2001-11-09 | Ricoh Co Ltd | 無溶剤型プラスチックフィルム液晶素子用シール剤及び表示素子 |
CN1217991C (zh) * | 2000-06-21 | 2005-09-07 | 三井化学株式会社 | 塑性液晶显示元件用密封剂组合物 |
JP2002088228A (ja) | 2000-09-14 | 2002-03-27 | Mitsui Chemicals Inc | 液晶表示素子用シール剤組成物ならびに液晶表示素子の製造方法 |
JP2002129127A (ja) * | 2000-10-20 | 2002-05-09 | Shin Etsu Polymer Co Ltd | 絶縁性接着剤、異方導電接着剤、ヒートシールコネクタ、及びヒートシールコネクタの製造方法 |
US6911109B2 (en) * | 2000-12-11 | 2005-06-28 | Henkel Corporation | Two-part, room temperature curable epoxy resin/ (meth)acrylate compositions and process for using same to bond substrates |
US6844034B2 (en) * | 2001-04-06 | 2005-01-18 | Exxonmobil Oil Corporation | Printable plastic film with printable coating comprising epoxy acrylate |
CA2446125A1 (en) * | 2001-05-16 | 2002-11-21 | Sekisui Chemical Co., Ltd. | Curing resin composition and sealants and end-sealing materials for displays |
US7438958B2 (en) * | 2002-11-01 | 2008-10-21 | Mitsui Chemicals, Inc. | Sealant composition for liquid crystal and process for producing liquid-crystal display panel with the same |
WO2004103949A1 (ja) * | 2003-05-23 | 2004-12-02 | Mitsui Chemicals, Inc. | (メタ)アクリル酸エステル化合物およびその用途 |
-
2004
- 2004-05-18 US US10/555,898 patent/US7678433B2/en not_active Expired - Fee Related
- 2004-05-18 CA CA002525178A patent/CA2525178A1/en not_active Abandoned
- 2004-05-18 KR KR1020057020718A patent/KR101194558B1/ko active IP Right Grant
- 2004-05-18 KR KR1020117030471A patent/KR20120003502A/ko not_active Application Discontinuation
- 2004-05-18 DE DE602004021928T patent/DE602004021928D1/de not_active Expired - Lifetime
- 2004-05-18 JP JP2005506333A patent/JP3921493B2/ja not_active Expired - Lifetime
- 2004-05-18 WO PCT/JP2004/006646 patent/WO2004104683A1/ja active Application Filing
- 2004-05-18 EP EP04733630A patent/EP1630594B1/en not_active Expired - Lifetime
- 2004-05-21 TW TW093114526A patent/TWI343504B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
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EP1630594A1 (en) | 2006-03-01 |
CA2525178A1 (en) | 2004-12-02 |
EP1630594B1 (en) | 2009-07-08 |
TWI343504B (en) | 2011-06-11 |
TW200527083A (en) | 2005-08-16 |
WO2004104683A1 (ja) | 2004-12-02 |
US7678433B2 (en) | 2010-03-16 |
EP1630594A4 (en) | 2006-06-14 |
US20070020405A1 (en) | 2007-01-25 |
KR20120003502A (ko) | 2012-01-10 |
KR101194558B1 (ko) | 2012-10-25 |
JP3921493B2 (ja) | 2007-05-30 |
DE602004021928D1 (de) | 2009-08-20 |
KR20060009282A (ko) | 2006-01-31 |
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