CN108351561A - Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element - Google Patents
Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element Download PDFInfo
- Publication number
- CN108351561A CN108351561A CN201780003640.XA CN201780003640A CN108351561A CN 108351561 A CN108351561 A CN 108351561A CN 201780003640 A CN201780003640 A CN 201780003640A CN 108351561 A CN108351561 A CN 108351561A
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- China
- Prior art keywords
- liquid crystal
- crystal display
- indicate
- methyl
- mentioned
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 158
- 239000003566 sealing material Substances 0.000 title claims abstract description 60
- 239000004020 conductor Substances 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 229920005989 resin Polymers 0.000 claims abstract description 70
- 239000011347 resin Substances 0.000 claims abstract description 70
- 239000000758 substrate Substances 0.000 claims abstract description 29
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- 239000011521 glass Substances 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
- 239000000853 adhesive Substances 0.000 claims abstract description 14
- 230000001070 adhesive effect Effects 0.000 claims abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 13
- 150000002118 epoxides Chemical class 0.000 claims abstract description 10
- 238000001029 thermal curing Methods 0.000 claims abstract description 10
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 6
- 150000002596 lactones Chemical class 0.000 claims abstract description 6
- 239000000565 sealant Substances 0.000 claims description 43
- 239000000126 substance Substances 0.000 claims description 21
- 239000003605 opacifier Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 5
- 239000011859 microparticle Substances 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 58
- -1 alkyl polyols Chemical class 0.000 description 54
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 45
- 239000004593 Epoxy Substances 0.000 description 43
- 150000002148 esters Chemical class 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 16
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 16
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 16
- 229960000380 propiolactone Drugs 0.000 description 16
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 15
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 13
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 13
- 239000010936 titanium Substances 0.000 description 13
- 229910052719 titanium Inorganic materials 0.000 description 13
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 11
- 230000014759 maintenance of location Effects 0.000 description 11
- VLSVVMPLPMNWBH-UHFFFAOYSA-N Dihydro-5-propyl-2(3H)-furanone Chemical compound CCCC1CCC(=O)O1 VLSVVMPLPMNWBH-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 10
- 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 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 150000002927 oxygen compounds Chemical class 0.000 description 8
- 238000007711 solidification Methods 0.000 description 7
- 230000008023 solidification Effects 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000006087 Silane Coupling Agent Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000007870 radical polymerization initiator Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- GNBCKKSGQPLTRW-UHFFFAOYSA-N C(C=C)(=O)OC.C(N)(O)=O Chemical compound C(C=C)(=O)OC.C(N)(O)=O GNBCKKSGQPLTRW-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940117927 ethylene oxide Drugs 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229960003742 phenol Drugs 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- AXPZIVKEZRHGAS-UHFFFAOYSA-N 3-benzyl-5-[(2-nitrophenoxy)methyl]oxolan-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC1OC(=O)C(CC=2C=CC=CC=2)C1 AXPZIVKEZRHGAS-UHFFFAOYSA-N 0.000 description 2
- XRUKRHLZDVJJSX-UHFFFAOYSA-N 4-cyanopentanoic acid Chemical class N#CC(C)CCC(O)=O XRUKRHLZDVJJSX-UHFFFAOYSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 2
- VZTQQYMRXDUHDO-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)phenyl]propan-2-yl]phenoxy]propyl] prop-2-enoate Chemical compound C=1C=C(OCC(O)COC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCC(O)COC(=O)C=C)C=C1 VZTQQYMRXDUHDO-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229950007687 macrogol ester Drugs 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000003405 preventing effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QRPLZGZHJABGRS-UHFFFAOYSA-N xi-5-Dodecanolide Chemical compound CCCCCCCC1CCCC(=O)O1 QRPLZGZHJABGRS-UHFFFAOYSA-N 0.000 description 2
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-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
- YWLLQUWZWIKQKV-UHFFFAOYSA-N 2-[hydroxy(methoxy)phosphoryl]oxyethyl prop-2-enoate Chemical class COP(O)(=O)OCCOC(=O)C=C YWLLQUWZWIKQKV-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- DAKZLOJXUDPQIL-UHFFFAOYSA-N 2-butyl-4-ethylphenol Chemical class CCCCC1=CC(CC)=CC=C1O DAKZLOJXUDPQIL-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical group CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
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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
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
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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
- 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
- C08G59/14—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
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1466—Acrylic or methacrylic acids
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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
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
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- C—CHEMISTRY; METALLURGY
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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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
Abstract
The object of the present invention is to provide can be obtained, excellent in adhesion, liquid crystal pollution is low, the sealing material for liquid crystal display device of the excellent liquid crystal display element of display performance.Further it is an object to manufactured conductive material and liquid crystal display element up and down using the sealing material for liquid crystal display device.The present invention is a kind of sealing material for liquid crystal display device, containing curable resin, also contains polymerization initiator and/or thermal curing agents, wherein the curable resin contains：Compound with 2 or more epoxy groups in following formula (1) compound represented and 1 molecule, in 100 parts by weight of curable resin, the content of the compound with 2 or more epoxy groups is 5 parts by weight or more and 25 parts by weight hereinafter, solidfied material is 290N/cm for the adhesive strength of glass substrate in 1 molecule2More than.In formula (1), R1Indicate hydrogen atom or methyl, R2Indicate group shown in following formula (2 1) or (2 2), R3Indicate the structure from acid anhydrides, R4Indicate that the structure from epoxide, X indicate that the open loop structure of lactone, n indicate that 1~6 integer, a indicate 1~4 integer.In formula (2 1), * indicates bonding position.In formula (2 2), b indicates that 0~8 integer, c indicate that 0~3 integer, d indicate that 0~8 integer, e indicate that 0~8 integer, any one of b, c, d are that 1 or more, * indicates bonding position.
Description
Technical field
The present invention relates to can be obtained, excellent in adhesion, liquid crystal pollution is low, display performance excellent liquid crystal display element
Sealing material for liquid crystal display device.Moreover, it relates to which manufactured using the sealing material for liquid crystal display device lead up and down
Logical material and liquid crystal display element.
Background technology
In recent years, as the manufacturing method of liquid crystal display element, from shorten productive temp time, liquid crystal usage amount it is optimal
From the perspective of change, used as patent document 1, it is disclosed Patent Document 2 used containing curable resin, light
The liquid crystal drop under type of the photo-thermal of polymerization initiator and thermal curing agents and the technique that is referred to as dripping with curing type sealant.
In technique of dripping, first, frame-shaped is formed on one in two electroded transparent substrates by distributing
Seal pattern.Next, the tiny droplets of liquid crystal to be added dropwise to the sealant on transparent substrate in the state that sealant is uncured
Frame in entire surface, be overlapped another transparent substrate immediately, the light such as ultraviolet light irradiated to sealing to carry out precuring.Thereafter,
It is heated to carry out main solidification, makes liquid crystal display element.It, can be with high by carrying out the fitting of substrate under reduced pressure
Efficiency system liquid making crystal display element, the technique of dripping become the mainstream of the manufacturing method of liquid crystal display element now.
In addition, in the present age that the various mobile devices with liquid crystal display panel such as mobile phone, portable game machine are popularized, dress
The miniaturization set is the project needed most.The method of miniaturization as device can enumerate the narrow architrave of liquid crystal display part, example
Such as the position of sealing is configured at below black matrix" (hereinafter also referred to narrow architrave designs).However, in the design of narrow architrave,
Since sealant is configured at the underface of black matrix", if carrying out technique of dripping, existing makes sealant photocuring when institute
The problem of light of irradiation is occluded, and light can not reach the inside of sealant, and solidification becomes inadequate.If sealant is consolidated as a result,
Change insufficient, then there are problems that uncured sealant ingredient dissolves out in liquid crystal and easy tos produce liquid crystal pollution.
Along with tablet terminal, mobile terminal it is universal, liquid crystal display element more required for impact test, fallen
The durability of experiment etc..In addition, being designed along with narrow architrave, it is desirable that the moisture-proof of driving under hot and humid environment etc. is reliable
Property, the performance of the immersion from external water is prevented to sealant further requirement.That is, from the resistance to punching for improving liquid crystal display element
From the perspective of hitting property, moisture-proof reliability, the cementability for improving sealant and substrate etc. is needed.However, making excellent in adhesion
And the sealant of liquid crystal pollution low (low liquid crystal pollution is excellent) is difficult.
Existing technical literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 2001-133794 bulletins
Patent document 2：Japanese Unexamined Patent Publication 5-295087 bulletins
Invention content
Problem to be solved by the invention
The present invention relates to can be obtained, excellent in adhesion, liquid crystal pollution is low, display performance excellent liquid crystal display element
Sealing material for liquid crystal display device.Further it is an object to be made using the sealing material for liquid crystal display device
Conductive material up and down and liquid crystal display element.
The means used to solve the problem
The present invention is a kind of sealing material for liquid crystal display device, containing curable resin, also contain polymerization initiator and/
Or thermal curing agents, wherein above-mentioned curable resin contains：There are 2 or more in following formula (1) compound represented and 1 molecule
The compound of epoxy group, in 100 parts by weight of curable resin, the content of the compound with 2 or more epoxy groups is in 1 molecule
More than 5 parts by weight and 25 parts by weight are hereinafter, solidfied material is 290N/cm for the adhesive strength of glass substrate2More than.
In formula (1), R1Indicate hydrogen atom or methyl, R2Indicate group shown in following formula (2-1) or (2-2), R3Expression source
From the structure of acid anhydrides, R4Indicate that the structure from epoxide, X indicate that the open loop structure of lactone, n indicate 1~6 integer, a
Indicate 1~4 integer.
In formula (2-1), * indicates bonding position.
In formula (2-2), b indicates that 0~8 integer, c indicate that 0~3 integer, d indicate that 0~8 integer, e indicate 0~8
Integer, any one of b, c, d are that 1 or more, * indicates bonding position.
Hereinafter, being described in detail to the present invention.
The present inventor works out by using above-mentioned formula (1) compound represented as curable resin, to available
The low sealant of the excellent in adhesion and liquid crystal pollution of sealing material for liquid crystal display device.However, the sealant obtained by use
In the case of, especially in fine liquid crystal display element, exists and have generation image retention, contrast reduction or answer speed
The case where reduction this problem.
Inventors believe that：The reason of image retention caused by display element etc. is on remaining in the solidfied material of sealant
It states formula (1) compound represented to be precipitated and be attached in alignment films, causes the reduction of orientation control force.I.e., it is believed that：Due to picture
In fine liquid crystal display element more than quantity of the plain density height to connect up, in the part for the sealant that the lower section of wiring configures
Become larger, causes light to be unable to fully reach sealant because of the wiring, unreacted above-mentioned formula (1) compound represented becomes prone to
It is precipitated.
Therefore, the present inventor further furthers investigate, as a result, it has been found that, by being applied in combination shown in above-mentioned formula (1)
Compound with 2 or more epoxy groups in compound and 1 molecule, and the change that will there is 2 or more epoxy groups in 1 molecule
The content for closing object is set as particular range, can obtain that excellent in adhesion, liquid crystal pollution is low, display performance is excellent to available
Liquid crystal display element sealing material for liquid crystal display device so that complete the present invention.
The sealing material for liquid crystal display device of the present invention contains curable resin.
Above-mentioned curable resin contains above-mentioned formula (1) compound represented.By containing chemical combination shown in above-mentioned formula (1)
Object, to which the excellent in adhesion of sealing material for liquid crystal display device of the present invention, liquid crystal pollution are low.
In above-mentioned formula (1), R2Indicate group shown in above-mentioned formula (2-1) or (2-2).Wherein, from the liquid crystal display of gained
From the perspective of the cementability of element sealant, the flexibility of solidfied material, above-mentioned R2Preferably b is 1~4, c 0, d are 0
Group (alkylidene oxide of the straight-chain of carbon number 1~4) shown in chemical formula (2-2).
In above-mentioned formula (1), R3Indicate the structure from acid anhydrides.
As above-mentioned acid anhydrides, can enumerate such as phthalic anhydride, maleic anhydride, succinic anhydride, citraconic anhydride.Its
In, preferably phthalic anhydride.
In above-mentioned formula (1), R4Indicate the structure from epoxide.
As above-mentioned epoxide, can use well and the chemical combination with 2 or more epoxy groups in aftermentioned 1 molecule
The identical compound of object.
In above-mentioned formula (1), X indicates the open loop structure of lactone.
As above-mentioned lactone, can enumerate for example beta-propiolactone, beta-butyrolactone, gamma-butyrolacton, gamma-valerolactone, in δ-penta
Ester, 6-caprolactone, γ-heptalactone, nonyl lactone, γ-decalactone, δ-decalactone, γ-dodecalactone, δ-dodecalactone, γ-
Undecalactone, delta-undeca lactone, 7- butyl -2- oxepane ketone etc..Wherein, preferably open loop when main framing linear fraction carbon
The lactone that number is 3~7.
In above-mentioned formula (1), n indicates 1~6 integer.Wherein, from the bonding of the sealing material for liquid crystal display device of gained
From the perspective of property, the flexibility of solidfied material, above-mentioned n is preferably 1~5 integer.
In above-mentioned formula (1), a indicates 1~4 integer.Wherein, consolidating from the sealing material for liquid crystal display device for improving gained
From the perspective of the heat resistance of compound, above-mentioned a is preferably 2~4 integer, from the viewpoint of storage stability, more preferably
2。
The preferred lower limit of the molecular weight of above-mentioned formula (1) compound represented is 700, preferred upper limit 2100.On making
State formula (1) compound represented molecular weight be the range, to gained sealing material for liquid crystal display device cementability and
Low liquid crystal pollution is better.
In 100 parts by weight of above-mentioned curable resin, the preferred lower limit of the content of above-mentioned formula (1) compound represented is 5 weights
Measure part, preferred upper limit is 50 parts by weight.By making the content of above-mentioned formula (1) compound represented be the range, to gained
The cementability of sealing material for liquid crystal display device and low liquid crystal pollution are better.The content of above-mentioned formula (1) compound represented
The more preferable upper limit be 30 parts by weight.
Above-mentioned curable resin, which contains in 1 molecule, has the compound of 2 or more epoxy groups (hereinafter also referred to as " multifunctional
Epoxide ").The reason of above-mentioned multi-functional epoxy compound is easily made into liquid crystal pollution, therefore do not influencing generally preferably
Use level is reduced in the range of cementability.It on the other hand, not will be above-mentioned in the sealing material for liquid crystal display device of the present invention
The content of multi-functional epoxy compound is set as the range only for the purpose of taking into account cementability and liquid crystal pollution, and is set to aftermentioned
Range.As a result, even if can inhibit that above-mentioned formula (1) institute is precipitated from solidfied material if using above-mentioned formula (1) compound represented
The compound shown inhibits the liquid crystal display element of gained that image retention etc. occurs and keeps display performance excellent.
As above-mentioned multi-functional epoxy compound, such as bisphenol A type epoxy compound, bisphenol F type epoxy chemical combination can be enumerated
Object, bisphenol S type epoxy compound, 2,2 '-diallyl bisphenol type ring oxygen compounds, A Hydrogenated Bisphenol A type ring oxygen compound, epoxy
Propane addition bisphenol A type epoxy compound, resorcinol type ring oxygen compound, biphenyl type epoxy compound, thioether-type epoxidation
Close object, diphenyl ether type ring oxygen compound, dicyclopentadiene type epoxy compound, naphthalene type ring oxygen compound, phenol novolak
Type ring oxygen compound, o-cresol novolak type epoxy compound, bicyclopentadiene novolac type epoxy compound, biphenyl line
Type novolak type epoxy compound, naphthols novolac type epoxy compound, glycidyl amine epoxy compound, alkyl polyols
Type ring oxygen compound, modified rubber type ring oxygen compound, epihydric alcohol ester compound etc..
In 100 parts by weight of above-mentioned curable resin, the lower limit of the content of above-mentioned multi-functional epoxy compound be 5 parts by weight,
The upper limit is 25 parts by weight.Content by making above-mentioned multi-functional epoxy compound is 5 parts by weight or more, to inhibit above-mentioned formula
(1) excellent effect of the precipitation of compound shown in can inhibit the liquid crystal display element of gained that image retention etc. occurs.It is above-mentioned by making
The content of multi-functional epoxy compound is 25 parts by weight hereinafter, to which the low liquid crystal of the sealing material for liquid crystal display device of gained is dirty
Metachromia is excellent.The preferred lower limit of the content of above-mentioned multi-functional epoxy compound is 7 parts by weight, preferred upper limit is 23 parts by weight, more
Preferred lower limit is 10 parts by weight, the more preferable upper limit is 20 parts by weight.
Above-mentioned curable resin in the range of not hindering the purpose of the present invention, in addition to formula (1) compound represented and on
It states except multi-functional epoxy compound, other curable resins can also be contained.
As above-mentioned other curable resins, the others (first for example in addition to formula (1) compound represented can be enumerated
Base) acrylic compounds, the compound with 1 epoxy group in 1 molecule (hereinafter also referred to as " monofunctional epoxy compound ")
Deng.
It should be noted that in the present specification, above-mentioned " (methyl) acrylic compounds " refer to acrylic compounds or metering system
Acids, above-mentioned " (methyl) acrylic compounds " refer to the compound with (methyl) acryloyl group, above-mentioned " (methyl) propylene
Acyl group " refers to acryloyl group or methylacryloyl.
As above-mentioned other (methyl) acrylic compounds, can enumerate for example by make to have the compound of hydroxyl with
(methyl) acrylic acid reaction obtained by (methyl) acrylate compounds, by making (methyl) acrylic acid be reacted with epoxide
Obtained by epoxy (methyl) acrylate, anti-by (methyl) acrylic acid derivative and isocyanate compound that make that there is hydroxyl
Carbamate obtained by answering (methyl) acrylate etc..Wherein, preferred epoxy (methyl) acrylate.In addition, above-mentioned (first
Base) acrylic compounds from the viewpoint of reactivity preferably in 1 molecule have 2 or more (methyl) acryloyl groups.
It should be noted that in the present specification, above-mentioned " (methyl) acrylate " refers to acrylate or metering system
Acid esters, above-mentioned " epoxy (methyl) acrylate " is that whole epoxy groups in epoxide is instigated to be reacted with (methyl) acrylic acid
Obtained by compound.
As the monofunctional compound in above-mentioned (methyl) acrylate compounds, such as (methyl) acrylic acid first can be enumerated
Ester, (methyl) ethyl acrylate, (methyl) propyl acrylate, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate,
(methyl) tert-butyl acrylate, (methyl) 2-EHA, (methyl) n-octyl, (methyl) acrylic acid are different pungent
Ester, the different nonyl ester of (methyl) acrylic acid, (methyl) isodecyl acrylate, (methyl) lauryl acrylate, the different meat of (methyl) acrylic acid
Cardamom ester, (methyl) stearyl acrylate, (methyl) acrylic acid 2- hydroxy methacrylates, (methyl) acrylic acid 2- hydroxy propyl esters, (first
Base) acrylic acid 2- hydroxybutyls, (methyl) acrylic acid 4- hydroxybutyls, (methyl) cyclohexyl acrylate, (methyl) acrylic acid is different
Norbornene ester, (methyl) acrylic acid dicyclopentenyl ester, (methyl) benzyl acrylate, (methyl) acrylic acid 2- methoxy acrylates, (first
Base) acrylic acid 2- ethoxy ethyl esters, (methyl) acrylic acid 2- butoxyethyls, (methyl) acrylic acid 2- phenoxy ethyls, (first
Base) acrylic methoxy glycol ester, (methyl) methoxyethyl macrogol ester, (methyl) acrylic acid phenoxy group diethyl two
Alcohol ester, (methyl) acrylic acid phenoxy group macrogol ester, (methyl) tetrahydrofurfuryl acrylate, (methyl) acrylic acid ethyl carbitol
Ester, (methyl) acrylic acid 2,2,2- trifluoro ethyl esters, 2,2,3,3- tetrafluoro propyl ester of (methyl) acrylic acid, (methyl) acrylic acid 1H, 1H,
5H- octafluoros pentyl ester, (methyl) propylene acid imide ester, (methyl) dimethylaminoethyl acrylate, (methyl) acrylic acid lignocaine
Ethyl ester, 2- (methyl) acryloyl-oxyethyls succinic acid, 2- (methyl) acryloyl-oxyethyls hexahydrophthalic acid, 2- (first
Base) acryloyl-oxyethyl 2- hydroxypropyl phthalates, 2- (methyl) acryloyl-oxyethyl phosphate, (methyl) third
Olefin(e) acid ethylene oxidic ester etc..
In addition, as 2 functional compounds in above-mentioned (methyl) acrylate compounds, such as 1,3-BDO can be enumerated
Two (methyl) acrylate, 1,4-butanediol two (methyl) acrylate, 1,6- hexylene glycols two (methyl) acrylate, 1,9- nonyls
Glycol two (methyl) acrylate, 1,10- decanediols two (methyl) acrylate, ethylene glycol two (methyl) acrylate, diethyl
Glycol two (methyl) acrylate, tetraethylene glycol two (methyl) acrylate, polyethylene glycol two (methyl) acrylate, the positive fourths of 2-
Base -2- ethyls -1,3-PD two (methyl) acrylate, dipropylene glycol two (methyl) acrylate, two (first of tripropylene glycol
Base) acrylate, polypropylene glycol two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, ethyleneoxide addition be double
Phenol A bis- (methyl) acrylate, propylene oxide addition bisphenol-A two (methyl) acrylate, two (first of ethyleneoxide addition Bisphenol F
Base) acrylate, dihydroxymethyl bicyclopentadiene two (methyl) acrylate, ethylene-oxide-modified isocyanuric acid two (methyl) third
Olefin(e) acid ester, 2- hydroxyls -3- (methyl) acryloxypropyl (methyl) acrylate, carbonate diol two (methyl) acrylic acid
Ester, polyetherdiol two (methyl) acrylate, polyester-diol two (methyl) acrylate, polycaprolactone glycol two (methyl) propylene
Acid esters, polybutadiene diol two (methyl) acrylate etc..
In addition, as compounds more than 3 functions in above-mentioned (methyl) acrylate compounds, such as three hydroxyls can be enumerated
Methylpropane three (methyl) acrylate, ethyleneoxide addition trimethylolpropane tris (methyl) acrylate, propylene oxide add
At trimethylolpropane tris (methyl) acrylate, caprolactone modification trimethylolpropane tris (methyl) acrylate, epoxy second
Alkane addition isocyanuric acid three (methyl) acrylate, glycerine three (methyl) acrylate, propylene oxide addition glycerine three (methyl)
Acrylate, pentaerythrite three (methyl) acrylate, three (methyl) acryloyl-oxyethyl phosphates, double trimethylolpropane
Four (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, two seasons penta 4
Alcohol six (methyl) acrylate etc..
As above-mentioned epoxy (methyl) acrylate, can enumerate for example epoxide is passed through with (methyl) acrylic acid it is normal
Product etc. obtained by rule method is reacted in the presence of basic catalyst.
As the epoxide as the raw material for synthesizing above-mentioned epoxy (methyl) acrylate, can use with it is upper
The identical substance of multi-functional epoxy compound stated.
As the commercially available product of above-mentioned epoxy (methyl) acrylate, can enumerate such as EBECRYL860, EBECRYL3200,
EBECRYL3201、EBECRYL3412、EBECRYL3600、EBECRYL3700、EBECRYL3701、EBECRYL3702、
EBECRYL3703, EBECRYL3800, EBECRYL6040, EBECRYL RDX63182 (are Daicel-Allnex companies
System), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (be chemical industrial company of the villages Xin Zhong
System), Epoxy Ester M-600A, Epoxy Ester 40EM, Epoxy Ester 70PA, Epoxy Ester 200PA,
Epoxy Ester 80MFA、Epoxy Ester 3002M、Epoxy Ester 3002A、Epoxy Ester 1600A、Epoxy
Ester 3000M, Epoxy Ester 3000A, Epoxy Ester 200EA, Epoxy Ester 400EA (are common prosperity society
Chemical company's system), Denacol Acrylate DA-141, Denacol Acrylate DA-314, Denacol Acrylate
DA-911 (being Nagase ChemteX Corporation systems) etc..
As above by making obtained by there is (methyl) acrylic acid derivative of hydroxyl to be reacted with isocyanate compound
Carbamate (methyl) acrylate, such as can be by having the isocyanates chemical combination of 2 isocyanate group relative to 1 equivalent
Object, make 2 equivalents have hydroxyl (methyl) acrylic acid derivative reacted in the presence of the tin based compound of catalytic amount and
.
As the isocyanate compound of the raw material as above-mentioned carbamate (methyl) acrylate, can enumerate for example
Isophorone diisocyanate, 2,4- toluene di-isocyanate(TDI)s, 2,6- toluene di-isocyanate(TDI)s, hexamethylene diisocyanate,
Trimethyl hexamethylene diisocyanate, 4,4 '-diisocyanate (MDI) of diphenyl methane-, hydrogenation MDI, polymeric MDI, 1,5-
Naphthalene diisocyanate, norbornene alkyl diisocyanate, tolidine diisocyanate, benzene dimethylene diisocyanate (XDI),
Hydrogenate XDI, lysine diisocyanate, triphenylmethane triisocyanate, three (isocyanatophenyl) thiophosphates, four
Xylene diisocyanate, 1,6,11- hendecane triisocyanates etc..
In addition, the isocyanate compound as the raw material as above-mentioned carbamate (methyl) acrylate, such as
It can also use through ethylene glycol, propylene glycol, glycerine, D-sorbite, trimethylolpropane, carbonate diol, polyetherdiol, gather
The isocyanic acid of chain elongation obtained by the reacting of the polyalcohols such as esterdiol, polycaprolactone glycol and excessive isocyanate compound
Ester compounds.
As the raw material as above-mentioned carbamate (methyl) acrylate, (methyl) acrylic acid with hydroxyl spreads out
Biology can enumerate such as (methyl) acrylic acid 2- hydroxy methacrylates, (methyl) acrylic acid 2- hydroxy propyl esters, (methyl) acrylic acid 2- hydroxyls
Single (methyl) hydroxyalkyl acrylates such as base butyl ester, (methyl) acrylic acid 4- hydroxybutyls, ethylene glycol, propylene glycol, 1,3- third
List (methyl) acrylate of the dihydric alcohols such as glycol, 1,3-BDO, 1,4-butanediol, polyethylene glycol, trimethylolethane, three
List (methyl) acrylate of the trihydroxylic alcohols such as hydroxymethyl-propane, glycerine or two (methyl) acrylate, bisphenol type epoxy acrylic acid
The epoxies such as ester (methyl) acrylate etc..
As the commercially available product of above-mentioned carbamate (methyl) acrylate, such as M-1100, M-1200, M- can be enumerated
1210, M-1600 (being East Asia Synesis Company system), EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270,
EBECRYL1290、EBECRYL2220、EBECRYL4827、EBECRYL4842、EBECRYL4858、EBECRYL5129、
EBECRYL6700, EBECRYL8402, EBECRYL8803, EBECRYL8804, EBECRYL8807, EBECRYL9260 (are
Daicel-Allnex corporations), Art Resin UN-330, Art Resin SH-500B, Art Resin UN-1200TPK,
Art Resin UN-1255、Art Resin UN-3320HB、Art Resin UN-7100、Art Resin UN-9000A、
Art Resin UN-9000H (being Gen Shang industrial groups system), U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6HA, U-
6LPA、U-10H、U-15HA、U-108、U-108A、U-122A、U-122P、U-324A、U-340A、U-340P、U-1084A、U-
2061BA、UA-340P、UA-4000、UA-4100、UA-4200、UA-4400、UA-5201P、UA-7100、UA-7200、UA-
W2A (being chemical industrial company of the villages Xin Zhong system), AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H,
UA-306I, UA-306T (being chemical company of common prosperity society system) etc..
As above-mentioned monofunctional epoxy compound, can enumerate such as (methyl) acrylic modified epoxy resin of part.
It should be noted that in the present specification, above-mentioned part (methyl) acrylic modified epoxy resin refers in 1 molecule
Compound with 1 epoxy group and 1 or more (methyl) acryloyl group, such as can be by making above-mentioned multi-functional epoxy compound
A part of epoxy group react and obtain with (methyl) acrylic acid.
It is above-mentioned others curable resin from the viewpoint of inhibiting liquid crystal pollution, preferably with-OH bases ,-NH- bases ,-
NH2The unit of the hydrogen bonds such as base.
The sealing material for liquid crystal display device of the present invention contains polymerization initiator and/or thermal curing agents.
As above-mentioned polymerization initiator, radical polymerization initiator can be used well.
As above-mentioned radical polymerization initiator, the hot radical generated free radicals by heating can be enumerated and polymerize initiation
Agent, the optical free radical polymerization initiator etc. generated free radicals by irradiated by light.
As above-mentioned optical free radical polymerization initiator, can enumerate for example benzophenone based compound, acetophenone based compound,
Acylphosphine oxide compound, titanocenes based compound, oxime ester based compound, benzoin ether based compound, thioxanthones etc..
As the commercially available product of above-mentioned optical free radical polymerization initiator, can enumerate such as IRGACURE184, IRGACURE369,
IRGACURE379、IRGACURE651、IRGACURE819、IRGACURE907、IRGACURE2959、IRGACURE OXE01、
Lucirin TPO (being BASF AG's system), benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (are Tokyo
Chemical conversion industry corporation), KR-02 (Light Chemical Company systems) etc..
As above-mentioned hot radical polymerization initiator, can enumerate such as comprising azo-compound, organic peroxide
Initiator.Wherein, the polymeric azo initiator of polymeric azo compound is preferably comprised.
It should be noted that in this specification, polymeric azo initiator refers to azo group and can be by heat
Compound that generation makes the cured free radical of (methyl) acryloxy, that number-average molecular weight is 300 or more.
The preferred lower limit of the number-average molecular weight of above-mentioned polymeric azo initiator is 1000, preferred upper limit is 300,000.Pass through
It is the range to make the number-average molecular weight of above-mentioned polymeric azo initiator, so as to prevent from causing harmful effect to liquid crystal, and
And it is easily mixed with curable resin.The more preferable lower limit of the number-average molecular weight of above-mentioned polymeric azo initiator be 5000,
The more preferable upper limit is 100,000, and further preferred lower limit is 10,000, the further preferred upper limit is 90,000.
It should be noted that in the present specification, above-mentioned number-average molecular weight is carried out using gel permeation chromatography (GPC)
The value for measuring and being found out based on polystyrene conversion.Divided equally based on number obtained by polystyrene conversion as being measured by GPC
Column when son amount, can enumerate such as Shodex LF-804 (Showa electrician corporation).
As above-mentioned polymeric azo initiator, can enumerate for example with via azo group by multiple polyalkylene oxides, poly- two
The compound of structure obtained by the bonding of the units such as methylsiloxane.
As the polymeric azo with structure obtained by being bonded the units such as multiple polyalkylene oxides via above-mentioned azo group
Initiator, it is however preferred to have the compound of polyethylene oxide structure.As this kind of polymeric azo initiator, such as 4 can be enumerated,
4 '-azos bis- (4- cyanopentanoic acids) are with condensation polymer, 4, the 4 '-azos bis- (4- cyanopentanoic acids) of polyalkylene glycol and with end
The condensation polymer etc. of the dimethyl silicone polymer of amino, can specifically enumerate such as VPE-0201, VPE-0401, VPE-0601,
VPS-0501, VPS-1001 (being and Wako Pure Chemical Industries corporation) etc..
In addition, as the example for not being high molecular azo-compound, can enumerate V-65, V-501 (is and the pure medicine work of light
Industry corporation) etc..
As above-mentioned organic peroxide, such as ketone peroxide, peroxy ketal, hydrogen peroxide, dialkyl group peroxide can be enumerated
Compound, peroxyester, diacyl peroxide, peroxy dicarbonate etc..
The content of above-mentioned polymerization initiator is 0.1 weight relative to whole 100 parts by weight of curable resin, preferred lower limit
Part, the preferred upper limit are 30 parts by weight.By making the content of above-mentioned polymerization initiator be the range, to the liquid crystal display of gained
Element sealant can maintain excellent storage stability, and curability is better.The content of above-mentioned polymerization initiator is more
Preferred lower limit is 1 parts by weight, the more preferable upper limit is 10 parts by weight, and the further preferred upper limit is 5 parts by weight.
As above-mentioned thermal curing agents, such as organic acid hydrazides, imdazole derivatives, amine compounds, polynary phenol system can be enumerated
Close object, acid anhydrides etc..Wherein, it is suitble to the organic acid hydrazides using solid.
As the organic acid hydrazides of above-mentioned solid, the bis- (acyls in diazanyl carbonyl ethyl -5- isopropyl second of such as 1,3- can be enumerated
Urea), sebacic dihydrazide, isophthalic dihydrazide, adipic dihydrazide, acid dihydrazide etc., as commercially available product, can lift
Go out such as SDH, ADH (great mound chemical company system), MDH (Japanese Finechem corporations), Amicure VDH, Amicure
VDH-J, Amicure UDH (being the fine scientific ＆ technical corporation's system of aginomoto) etc..
The content of above-mentioned thermal curing agents relative to whole 100 parts by weight of curable resin, preferred lower limit be 1 parts by weight,
The preferred upper limit is 50 parts by weight.By making the content of above-mentioned thermal curing agents be the range, to the liquid crystal display element of gained
Excellent coating, storage stability can be maintained with sealant, and curability is better.The content of above-mentioned thermal curing agents is more
Preferred upper limit is 30 parts by weight.
The sealing material for liquid crystal display device of the present invention preferably comprises inhibition from the viewpoint of improving storage stability etc.
Agent.
As above-mentioned polymerization inhibitor, such as 2,6- di-t-butyls cresols, butylated hydroxy anisole, 2,6-, bis--uncles can be enumerated
Butyl -4- ethyl -phenols, stearyl β-(3,5- di-t-butyl -4- hydroxy phenyls) propionic ester, 2,2 '-di-2-ethylhexylphosphine oxide (4- first
Base -6- tert-butyl phenols), 2,2 '-methylene-bis(4-ethyl-6-t-butyl phenol)s, 4,4 '-thiobis (3- methyl-6-tert-butyls
Base phenol), 4,4- butylidene-bis(3-methyl-6-t-butyl phenol)s, bis- (1, the 1- dimethyl -2- (β-(3- tertiary butyls -4- of 3,9-
Hydroxy-5-methyl base phenyl) propionyloxy) ethyl) -2,4,8,10- tetra- oxaspiro (5,5) hendecanes, four-(methylene -3- (3 ',
5 ' -4 '-hydroxy phenyls of di-t-butyl -) propionic ester) methane, 1,3,5- tri- (3 ', 5 ' -4 '-hydroxybenzyls of di-t-butyl -) -
Sec- triazines -2,4,6- (1H, 3H, 5H) triketone, quinhydrones, p methoxy phenol etc..
For the content of above-mentioned polymerization inhibitor relative to 100 parts by weight of curable resin, preferred lower limit is 0.005 parts by weight, excellent
The upper limit of choosing is 0.2 parts by weight.By making the content of above-mentioned polymerization inhibitor be the range, so as to maintain the liquid crystal display member of gained
The excellent curability of part sealant, and can further play the effect for improving storage stability etc..Above-mentioned polymerization inhibitor
Content more preferable lower limit be 0.007 parts by weight, the more preferable upper limit is 0.18 parts by weight.
For the sealing material for liquid crystal display device of the present invention, to improve viscosity, based on stress dispersion effect come further
For the purpose of improving cementability, the moisture-proof for improving linear expansivity, raising solidfied material etc., filler is preferably comprised.
As above-mentioned filler, can enumerate for example silica, talcum, bead, asbestos, gypsum, diatomite, terre verte,
Bentonite, montmorillonite, sericite, atlapulgite, aluminium oxide, zinc oxide, iron oxide, magnesia, tin oxide, titanium oxide, carbonic acid
The inorganic fillers such as calcium, magnesium carbonate, magnesium hydroxide, aluminium hydroxide, aluminium nitride, silicon nitride, barium sulfate, calcium silicates, polyester micropartical,
The organic fillers such as polyurethane particulate, polyvinyl particle, acrylic polymer particle.
In 100 parts by weight of sealing material for liquid crystal display device of the present invention, the preferred lower limit of the content of above-mentioned filler is
10 parts by weight, preferred upper limit are 70 parts by weight.Content by making above-mentioned filler is the range, to can inhibit coating etc.
Deterioration, and can further play the effect for improving cementability etc..The more preferable lower limit of the content of above-mentioned filler is 20 weights
Measure part, the more preferable upper limit is 60 parts by weight.
The sealing material for liquid crystal display device of the present invention is preferably comprised silane coupled for the purpose of further increasing cementability
Agent.Above-mentioned silane coupling agent mainly has the function of as by bonding additives be bonded well such as sealant and substrates.
As above-mentioned silane coupling agent, such as 3- TSL 8330s, 3- mercaptopropyis can be used well
Trimethoxy silane, 3- glycidoxypropyltrime,hoxysilanes etc..
The present invention 100 parts by weight of sealing material for liquid crystal display device in, the content of above-mentioned silane coupling agent it is preferred under
It is limited to 0.1 parts by weight, preferred upper limit is 10 parts by weight.Content by making above-mentioned silane coupling agent is the range, so as to press down
The generation of liquid crystal pollution processed, and further play the effect for improving cementability.The content of above-mentioned silane coupling agent it is more preferable
Lower limit is 0.3 parts by weight, the more preferable upper limit is 5 parts by weight.
The sealing material for liquid crystal display device of the present invention can also contain opacifier.By containing above-mentioned opacifier, this hair
Bright sealing material for liquid crystal display device can be suitable as shading sealant.
As above-mentioned opacifier, black such as iron oxide, titanium, nigrosine, Hua Jing black, fullerene, carbon black, resin packet can be enumerated
Cover type carbon black etc..Wherein, preferably titanium is black.
Above-mentioned titanium is black be compared to the average transmittance of the light for 300~800nm of wavelength, it is attached for ultraviolet range
The higher substance of transmissivity of close, particularly 370~450nm of wavelength light.That is, it is the shading for having following properties that above-mentioned titanium is black
Agent：By will be seen that the light of the wavelength in light region fully covers, to be assigned to the sealing material for liquid crystal display device of the present invention
Light-proofness is given, on the other hand, makes the light transmission of the wavelength near ultraviolet range.As the used for liquid crystal display element close of the present invention
Opacifier contained by envelope agent, the preferably high substance of insulating properties, the opacifier high as insulating properties, titanium are black also suitable.
Above-mentioned titanium is black to play sufficient effect non-surface treated, but surface can also be used through coupling agent etc.
The titanium of organic principle processing is black or by the inorganic constituents packet such as silica, titanium oxide, germanium oxide, aluminium oxide, zirconium oxide, magnesia
The surface treated titaniums such as the titanium that covers is black are black.Wherein, the titanium handled using organic principle is black because that can further increase insulating properties
This point and it is preferred that.
In addition, using the liquid of the sealing material for liquid crystal display device manufacture containing the black present invention as opacifier of above-mentioned titanium
Crystal display element has sufficient light-proofness, therefore can realize no light leakage, be shown with high contrast, with excellent image
The liquid crystal display element of quality.
The commercially available product black as above-mentioned titanium, it (is Mitsubishi's synthesis that can enumerate such as 12S, 13M, 13M-C, 13R-N, 14M-C
Material Co. Ltd. system), Tillack D (red fringe chemical conversion corporation) etc..
The preferred lower limit of the black specific surface area of above-mentioned titanium is 13m2/ g, preferred upper limit 30m2/ g, more preferable lower limit are
15m2/ g, the more preferable upper limit are 25m2/g。
In addition, the preferred lower limit of the black volume resistance of above-mentioned titanium is 0.5 Ω cm, preferred upper limit is 3 Ω cm, more preferably
Lower limit is 1 Ω cm, the more preferable upper limit is 2.5 Ω cm.
The primary particle size of above-mentioned opacifier as long as liquid crystal display element substrate between distance hereinafter, as long as do not limit especially
Fixed, preferred lower limit is 1nm, the preferred upper limit is 5 μm.By making the primary particle size of above-mentioned opacifier be the range, so as to
It is enough to keep coating more excellent under the premise of so that viscosity, the thixotropy of the sealing material for liquid crystal display device of gained is significantly increased
It is different.The more preferable lower limit of the primary particle size of above-mentioned opacifier is 5nm, the more preferable upper limit is 200nm, and further preferred lower limit is
10nm, the further preferred upper limit are 100nm.
It should be noted that the primary particle size of above-mentioned opacifier can use particles distribution instrument (for example, PARTICLE
SIZING SYSTEMS corporations, " NICOMP 380ZLS ") it is measured.
In 100 parts by weight of sealing material for liquid crystal display device of the present invention, the preferred lower limit of the content of above-mentioned opacifier is 5
Parts by weight, preferred upper limit are 80 parts by weight.By making the content of above-mentioned opacifier be the range, so as to not reduce gained
The cementability of sealing material for liquid crystal display device, further play under the premise of the intensity after solidification and drafting property and improve shading
The effect of property.The more preferable lower limit of the content of above-mentioned opacifier is 10 parts by weight, the more preferable upper limit is 70 parts by weight, further excellent
It is 30 parts by weight to select lower limit, the further preferred upper limit is 60 parts by weight.
The sealing material for liquid crystal display device of the present invention can also further contain stress relaxation agent, reactivity as needed
Diluent shakes the additives such as change agent, spacer, curing accelerator, antifoaming agent, levelling agent.
As manufacture the present invention sealing material for liquid crystal display device method, can enumerate for example using homogenous disperse machine,
The mixing machines such as homogeneous mixer, universal mixer, planetary-type mixer, kneader, three-roller draw curable resin, polymerization
Send out the method etc. of the additives mixing such as agent and/or thermal curing agents and the silane coupling agent being added as needed on.
For the sealing material for liquid crystal display device of the present invention, solidfied material is for the lower limit of the adhesive strength of glass substrate
290N/cm2.By making above-mentioned adhesive strength be 290N/cm2More than, to keep the impact resistance of the liquid crystal display element of gained excellent
It is different.The preferred lower limit of above-mentioned adhesive strength is 310N/cm2, more preferable lower limit be 330N/cm2。
The higher the better for above-mentioned adhesive strength, and without the preferred upper limit, but the upper limit of essence is 400N/cm2。
It should be noted that above-mentioned solidfied material can measure the adhesive strength of glass substrate by the following method.
First, sealing material for liquid crystal display device is coated on glass substrate, another glass substrate is overlapped thereon and
So that sealing material for liquid crystal display device is spread out, irradiates 100mW/cm2Ultraviolet light after 30 seconds, with 120 DEG C heat within 1 hour,
Thus adhesive test piece is made.Next, for the adhesive test piece of gained, can be measured by using tensometer above-mentioned solid
Adhesive strength of the compound for glass substrate.
The sealing material for liquid crystal display device of the present invention is suitable for the solidification under high temperature, preferably makes its solidification with 100 DEG C or more
It uses, more preferably so that its solidification is used with 110 DEG C or more.
By coordinating electrically conductive microparticle in the sealing material for liquid crystal display device of the present invention, conductive material up and down can be manufactured
Material.The conductive material up and down of sealing material for liquid crystal display device and electrically conductive microparticle containing the present invention is also one of present invention.
As above-mentioned electrically conductive microparticle, the surface in metal ball, resin particle can be used to be formed with conductive metal layer
Particle etc..Wherein, the particle of conductive metal layer energy due to the excellent elasticity of resin particle is formed on the surface of resin particle
It is enough to be conductively connected in the case where not damaging transparent substrate etc., it is therefore preferred.
The manufactured liquid crystal using the sealing material for liquid crystal display device of the present invention or the conductive material up and down of the present invention
Show that element is also one of present invention.
Even if the sealing material for liquid crystal display device of the present invention is in the aperture opening ratio of the sealant of the liquid crystal display element of gained
It in the case of low, can also inhibit that image retention etc. occurs, it is excellent to the display performance of the liquid crystal display element, therefore can use well
In the low liquid crystal display element of the aperture opening ratio of sealant.Specifically, the sealing material for liquid crystal display device of the present invention is suitble to use
It is 50% liquid crystal display element below in the aperture opening ratio of sealant, the aperture opening ratio for being particularly suited for sealant is 30% below
Liquid crystal display element.
The ratio of hiding part such as do not connected up it should be noted that above-mentioned " aperture opening ratio of sealant " refers to sealant
Example can be measured by using light microscope to observe the shape of the metal line on the top that is configured at sealant.
The sealing material for liquid crystal display device of the present invention can be suitable for the liquid crystal display element based on liquid crystal dripping process
Manufacture.
As the method for manufacturing the liquid crystal display element of the present invention according to liquid crystal dripping process, specifically, can enumerate
Such as method etc. with the following process：Pass through the liquid crystal of the coating present invention such as silk-screen printing, distributor coating on substrate
The process for showing element sealant etc. to form the seal pattern of frame-shaped；The present invention sealing material for liquid crystal display device etc. not
The tiny droplets of liquid crystal are added dropwise to entire surface in the frame for being applied to transparent substrate in the state of solidification, are overlapped the work of another substrate immediately
Sequence；And sealant is made to light such as the seal pattern partial illumination ultraviolet lights of sealing material for liquid crystal display device etc. of the present invention
The process of precuring；And the sealant through precuring is heated to make it lead cured process.
Invention effect
According to the present invention, it is possible to provide the liquid crystal that excellent in adhesion, liquid crystal pollution is low, display performance is excellent can be obtained
Show the sealing material for liquid crystal display device of element.In addition, according to the present invention, it is possible to provide use the sealing material for liquid crystal display device
And manufactured conductive material and liquid crystal display element up and down.
Specific implementation mode
Hereinafter, embodiment is enumerated the present invention is described in more detail, but the present invention is not limited only to these embodiments.
(making of curable resin A)
Acrylic acid 2- hydroxy methacrylates 116 parts by weight, 114 parts by weight of beta-propiolactone are added in reaction flask and as resistance
After being stirred 5 hours at 90 DEG C using bell-type electric heater, 148 parts by weight of phthalic anhydride are added in 0.3 parts by weight of quinhydrones of poly- agent
And it futher stirs 5 hours.Next, 170 parts by weight of bisphenol A diglycidyl ether are added in the reactant of gained, 90
DEG C stirring 5 hours, thus obtain curable resin A.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin A is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in following formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in following formula (4), X is following formula
(5) open loop structure of beta-propiolactone shown in, n=2, a=2).
In formula (3), * indicates bonding position.
In formula (4), * indicates bonding position.
In formula (5), * indicates bonding position.
(making of curable resin B)
Other than the use level of beta-propiolactone is changed to 360 parts by weight, with above-mentioned " (making of curable resin A) "
It similarly operates, obtains curable resin B.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin B is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is above-mentioned formula
(5) open loop structure of beta-propiolactone shown in, n=5, a=2).
(making of curable resin C)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 200 parts by weight of gamma-valerolactone, with above-mentioned " (curability
The making of Resin A) " similarly operate, obtain curable resin C.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin C is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is following formula
(6) open loop structure of gamma-valerolactone shown in, n=2, a=2).
In formula (6), * indicates bonding position.
(making of curable resin D)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 500 parts by weight of gamma-valerolactone, with above-mentioned " (curability
The making of Resin A) " similarly operate, obtain curable resin D.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin D is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is above-mentioned formula
(6) open loop structure of gamma-valerolactone shown in, n=5, a=2).
(making of curable resin E)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 114 parts by weight of 6-caprolactone, with above-mentioned " (curability tree
The making of fat A) " similarly operate, obtain curable resin E.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin E is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is following formula
(7) open loop structure of 6-caprolactone shown in, n=1, a=2).
In formula (7), * indicates bonding position.
(making of curable resin F)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 228 parts by weight of 6-caprolactone, with above-mentioned " (curability tree
The making of fat A) " similarly operate, obtain curable resin F.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin F is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is above-mentioned formula
(7) open loop structure of 6-caprolactone shown in, n=2, a=2).
(making of curable resin G)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 342 parts by weight of 6-caprolactone, with above-mentioned " (curability tree
The making of fat A) " similarly operate, obtain curable resin G.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin G is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is above-mentioned formula
(7) open loop structure of 6-caprolactone shown in, n=3, a=2).
(making of curable resin H)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 456 parts by weight of 6-caprolactone, with above-mentioned " (curability tree
The making of fat A) " similarly operate, obtain curable resin H.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin H is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is above-mentioned formula
(7) open loop structure of 6-caprolactone shown in, n=4, a=2).
(making of curable resin I)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 570 parts by weight of 6-caprolactone, with above-mentioned " (curability tree
The making of fat A) " similarly operate, obtain curable resin I.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin I is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is above-mentioned formula
(7) open loop structure of 6-caprolactone shown in, n=5, a=2).
(making of curable resin J)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 684 parts by weight of 6-caprolactone, with above-mentioned " (curability tree
The making of fat A) " similarly operate, obtain curable resin J.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin J is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is above-mentioned formula
(7) open loop structure of 6-caprolactone shown in, n=6, a=2).
(making of curable resin K)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 256 parts by weight of γ-heptalactone, with above-mentioned " (curability
The making of Resin A) " similarly operate, obtain curable resin K.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin K is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is following formula
(8) open loop structure of γ-heptalactone shown in, n=2, a=2).
In formula (8), * indicates bonding position.
(making of curable resin L)
Other than substituting 114 parts by weight of beta-propiolactone and coordinating 640 parts by weight of γ-heptalactone, with above-mentioned " (curability
The making of Resin A) " similarly operate, obtain curable resin L.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin L is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the structure of bisphenol A diglycidyl ether shown in above-mentioned formula (4), X is above-mentioned formula
(8) open loop structure of γ-heptalactone shown in, n=5, a=2).
(making of curable resin M)
It substitutes 114 parts by weight of beta-propiolactone and coordinates 342 parts by weight of 6-caprolactone, substitute bisphenol A diglycidyl ether 170
Parts by weight and coordinate three (p-hydroxybenzene) methane diglycidyl ethers, 230 parts by weight, in addition to this, with above-mentioned " (curability tree
The making of fat A) " similarly operate, obtain curable resin M.
Pass through1H-NMR、13C-NMR and FT-IR analyses, it is thus identified that curable resin M is above-mentioned formula (1) compound represented
(R1For hydrogen atom, R2For group (b=2, c=0, d=0), R shown in above-mentioned formula (2-2)3To be originated from shown in above-mentioned formula (3)
The structure of phthalic anhydride, R4To be originated from the knot of three (p-hydroxybenzene) methane diglycidyl ethers shown in following formula (9)
Structure, X are the open loop structure of 6-caprolactone shown in above-mentioned formula (7), n=3, a=2).
In formula (9), * indicates bonding position.
(making of part acrylic acid modified bisphenol F type epoxy resin)
So that 312 parts by weight of Bisphenol F diglycidyl ether is dissolved in toluene 600mL, triphenylphosphine is added in the solution
Uniform solution is made in 0.2g.After 2 hours dropwise addition 72 parts by weight of acrylic acid being taken in the solution of gained under return stirring,
And then carry out 6 hours return stirrings.Next, by removing toluene, obtains part acrylic acid shown in following formula (10) and be modified
Bisphenol f type epoxy resin.
(embodiment 1~17, the Comparative Examples 1 to 5)
According to the match ratio recorded in table 1~3, by each material planetary agitating device (Thinky corporations, " ぁ わ
と り Practice Taros ") stirring after, equably mixed using ceramic three-roller, obtain embodiment 1~17, the liquid crystal of the Comparative Examples 1 to 5
Show element sealant.
<Evaluation>
For each sealing material for liquid crystal display device obtained in Examples and Comparative Examples, conduct the following evaluation.Knot
Fruit is shown in table 1~and 3.
(storage stability)
Each sealing material for liquid crystal display device obtained in Examples and Comparative Examples is put into syringe, it is de- using vacuum
Vacuum defoamation 10 minutes under conditions of 1500rpm, 3 support bulb apparatus (Thinky corporations, " ARV-200 "), 23 DEG C of temperature,
After placing 2 weeks in the environment of humidity 50%RH, a small amount of and hardened coating is taken out in glass substrate with spatula, investigates the solidifying of sealant
Whether gelatinization carries out.
The case where non-gelation can be easy to be coated on glass substrate, is denoted as "○", and gelation and coating will occur
The case where deterioration, is denoted as " △ ", will be unable to be denoted as "×" the case where coating, to have rated storage stability.
(cementability)
Relative to 100 parts by weight of each sealing material for liquid crystal display device obtained in Examples and Comparative Examples, planet is used
Formula agitating device makes polymeric beads (ponding chemical industrial company system, " Micropearl SP ") 3 parts by weight of 5 μm of average grain diameter
Disperse uniform solution is made.It will be in the atomic measurement of the solution of gained to glass substrate (20mm × 50mm × 1.1mmt)
Centre portion is overlapped the glass substrate of homotype, sealing material for liquid crystal display device is made to spread out on it.In this state, it irradiates
100mW/cm2Ultraviolet light after 30 seconds, with 120 DEG C heat within 1 hour, obtain adhesive test piece.
To the adhesive test piece of gained, adhesive strength is measured using tensometer.
(display performance (preventing property of image retention) of liquid crystal display element)
Liquid crystal (Chisso corporations, " JC-5001LA ") 0.5g is added in sample bottle, is added in Examples and Comparative Examples
In obtained each sealant for liquid crystal dripping process 0.1g and after rocking, heated 1 hour with 120 DEG C, be down to room temperature (25 DEG C).
In the alignment films of the glass substrate with transparent electrode and alignment films (Nissan Chemical corporation, " SE7492 "),
Each liquid crystal dripping process obtained in Examples and Comparative Examples is coated in a manner of being depicted as the frame of square with distributor to use
Sealant.Next, by entire surface in the frame being applied on substrate is added dropwise from the tiny droplets of the liquid crystal taken out in above-mentioned sample bottle,
It is overlapped another glass substrate in a vacuum.Vacuum is released, 100mW/cm is irradiated2Ultraviolet light after 30 seconds, it is small with 120 DEG C of heating 1
When, thus make sealant cures, obtains liquid crystal display element (aperture opening ratio 20% of sealant).
About the liquid crystal display element of gained, visual confirmation applies the direct current of 1V while applying the alternating voltage of 1.5V
A situation arises for image retention when voltage.As a result, the case where not confirming image retention completely is denoted as "○", a small amount of image retention is confirmed
Situation is denoted as " △ ", and the case where confirming serious image retention is denoted as "×", to have rated the display performance of liquid crystal display element
(preventing property of image retention).
(display performance (low liquid crystal pollution) of liquid crystal display element)
In the alignment films of the glass substrate with transparent electrode and alignment films (Nissan Chemical corporation, " SE7492 "),
Each liquid crystal dripping process obtained in Examples and Comparative Examples is coated in a manner of being depicted as the frame of square with distributor to use
Sealant.Next, the tiny droplets of liquid crystal (Chisso corporations, " JC-5001LA ") are added dropwise in the frame being applied on substrate
Entire surface is overlapped another glass substrate in a vacuum.Vacuum is released, irradiates 100mW/cm with covering display unit2Ultraviolet light 30
After second, is heated 1 hour with 120 DEG C, thus make sealant cures, obtain liquid crystal display element (aperture opening ratio 20% of sealant).
About the liquid crystal display element of gained, the sealant periphery of display unit is confirmed using petrographic microscope.As a result, will completely not
It confirms the uneven situation of display and is denoted as "○", will confirm that the uneven situation of a small amount of display is denoted as " △ ", will confirm that serious
The uneven situation of display be denoted as "×", to have rated the display performance (low liquid crystal pollution) of liquid crystal display element.
(impact resistance of liquid crystal display element)
About each sealing material for liquid crystal display device obtained in Examples and Comparative Examples, with above-mentioned " (liquid crystal display member
The display performance (low liquid crystal pollution) of part) " similarly operate, each 10 units of liquid crystal display element are made respectively.
Into the drop test exercised each liquid crystal display element and fallen from the height of 2m, after drop test, by the unit of whole
There is a situation where the liquid crystal leakages caused by peeling off, rupturing to be denoted as "○", will be more than 1 unit and 9 units are below
There is a situation where liquid crystal leakages to be denoted as " △ " for liquid crystal display element, and by whole liquid crystal display elements, there is a situation where liquid crystal leakages
It is denoted as "×", to have rated the impact resistance of liquid crystal display element.
[table 1]
[table 2]
[table 3]
Industrial availability
According to the present invention, it is possible to provide the liquid crystal that excellent in adhesion, liquid crystal pollution is low, display performance is excellent can be obtained
Show the sealing material for liquid crystal display device of element.In addition, according to the present invention, it is possible to provide use the sealing material for liquid crystal display device
And manufactured conductive material and liquid crystal display element up and down.
Claims (6)
1. a kind of sealing material for liquid crystal display device, which is characterized in that containing curable resin, also contain polymerization initiator and/
Or thermal curing agents, wherein
The curable resin contains：Chemical combination with 2 or more epoxy groups in following formula (1) compound represented and 1 molecule
Object,
In 100 parts by weight of curable resin, the content of the compound with 2 or more epoxy groups is 5 parts by weight or more in 1 molecule
And 25 parts by weight hereinafter,
Solidfied material is 290N/cm for the adhesive strength of glass substrate2More than,
In formula (1), R1Indicate hydrogen atom or methyl, R2Indicate group shown in following formula (2-1) or (2-2), R3It indicates to be originated from acid
The structure of acid anhydride, R4Indicate that the structure from epoxide, X indicate that the open loop structure of lactone, n indicate that 1~6 integer, a indicate
1~4 integer,
In formula (2-1), * indicates bonding position,
In formula (2-2), b indicate 0~8 integer, c indicate 0~3 integer, d indicate 0~8 integer, e indicate 0~8 it is whole
Number, any one of b, c, d are that 1 or more, * indicates bonding position.
2. sealing material for liquid crystal display device according to claim 1, which is characterized in that 100 parts by weight of curable resin
In, the content of formula (1) compound represented is 5~50 parts by weight.
3. sealing material for liquid crystal display device according to claim 1 or 2, which is characterized in that contain polymerization inhibitor.
4. sealing material for liquid crystal display device according to claim 1,2 or 3, which is characterized in that contain opacifier.
5. a kind of conductive material up and down, which is characterized in that containing used for liquid crystal display element close described in claim 1,2,3 or 4
Seal agent and electrically conductive microparticle.
6. a kind of liquid crystal display element, which is characterized in that be using used for liquid crystal display element described in claim 1,2,3 or 4
Conductive material up and down described in sealant or claim 5 and it is manufactured.
Applications Claiming Priority (3)
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| JP2016-098916 | 2016-05-17 | ||
| JP2016098916 | 2016-05-17 | ||
| PCT/JP2017/018181 WO2017199905A1 (en) | 2016-05-17 | 2017-05-15 | Sealing agent for liquid crystal display elements, vertically conducting material and liquid crystal display element |
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| CN108351561A true CN108351561A (en) | 2018-07-31 |
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| KR (1) | KR102426816B1 (en) |
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| JP6650151B2 (en) * | 2018-04-03 | 2020-02-19 | 協立化学産業株式会社 | Curable composition, liquid crystal panel, and method of manufacturing liquid crystal panel |
| JP6699713B1 (en) * | 2018-11-28 | 2020-05-27 | 東洋インキＳｃホールディングス株式会社 | display |
| CN115004094A (en) * | 2020-03-02 | 2022-09-02 | 三井化学株式会社 | Sealant for liquid crystal dropping process and manufacturing method of liquid crystal display panel |
| WO2023182245A1 (en) * | 2022-03-25 | 2023-09-28 | 積水化学工業株式会社 | Liquid crystal display element sealant and liquid crystal display element |
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| JP2004361854A (en) * | 2003-06-06 | 2004-12-24 | Sekisui Chem Co Ltd | Liquid crystal display element |
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| CN101978313A (en) * | 2008-03-26 | 2011-02-16 | 积水化学工业株式会社 | Sealing material for liquid-crystal dropping process, vertical-conduction material, and liquid-crystal display element |
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| WO2017199905A1 (en) | 2017-11-23 |
| TW201811854A (en) | 2018-04-01 |
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| KR20190008172A (en) | 2019-01-23 |
| JP6263317B1 (en) | 2018-01-17 |
| KR102426816B1 (en) | 2022-07-28 |
| TWI733805B (en) | 2021-07-21 |
| JPWO2017199905A1 (en) | 2018-06-07 |
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