CN107636524B - Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element - Google Patents
Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element Download PDFInfo
- Publication number
- CN107636524B CN107636524B CN201780001784.1A CN201780001784A CN107636524B CN 107636524 B CN107636524 B CN 107636524B CN 201780001784 A CN201780001784 A CN 201780001784A CN 107636524 B CN107636524 B CN 107636524B
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- meth
- crystal display
- display element
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 111
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 title abstract description 11
- 238000007789 sealing Methods 0.000 title description 5
- 239000000565 sealant Substances 0.000 claims abstract description 77
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 31
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 14
- 238000001029 thermal curing Methods 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 101
- 239000004593 Epoxy Substances 0.000 claims description 33
- 239000010419 fine particle Substances 0.000 claims description 13
- 239000004020 conductor Substances 0.000 claims 2
- 238000011109 contamination Methods 0.000 abstract description 16
- 239000011248 coating agent Substances 0.000 abstract description 12
- 238000000576 coating method Methods 0.000 abstract description 12
- 230000002265 prevention Effects 0.000 abstract description 8
- -1 acrylic compound Chemical class 0.000 description 52
- 239000003822 epoxy resin Substances 0.000 description 46
- 229920000647 polyepoxide Polymers 0.000 description 46
- 239000000047 product Substances 0.000 description 32
- 239000000758 substrate Substances 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 14
- 230000035699 permeability Effects 0.000 description 14
- 239000010936 titanium Substances 0.000 description 14
- 229910052719 titanium Inorganic materials 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 239000003999 initiator Substances 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 11
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 7
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 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 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 230000002542 deteriorative effect Effects 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- 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
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 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 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide 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
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 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
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-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
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 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
- 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
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 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
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- NQUXRXBRYDZZDL-UHFFFAOYSA-N 1-(2-prop-2-enoyloxyethyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1(CCOC(=O)C=C)C(O)=O NQUXRXBRYDZZDL-UHFFFAOYSA-N 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- FTPCDYQZRDDWEJ-UHFFFAOYSA-N 2-(2-hydroxypropyl)-6-(2-prop-2-enoyloxyethoxycarbonyl)benzoic acid Chemical compound CC(O)CC1=CC=CC(C(=O)OCCOC(=O)C=C)=C1C(O)=O FTPCDYQZRDDWEJ-UHFFFAOYSA-N 0.000 description 1
- IEQWWMKDFZUMMU-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)CCOC(=O)C=C IEQWWMKDFZUMMU-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
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-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
- JYDNIBKTTUPPIR-UHFFFAOYSA-N 2-[3-(2-hydroxyphenyl)phenyl]phenol Chemical compound OC1=CC=CC=C1C1=CC=CC(C=2C(=CC=CC=2)O)=C1 JYDNIBKTTUPPIR-UHFFFAOYSA-N 0.000 description 1
- RUVNKAUVVBCURD-UHFFFAOYSA-N 2-[[4-[2-[4-(oxiran-2-ylmethoxy)-3-prop-2-enylphenyl]propan-2-yl]-2-prop-2-enylphenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C(CC=C)=CC=1C(C)(C)C(C=C1CC=C)=CC=C1OCC1CO1 RUVNKAUVVBCURD-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
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-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
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-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
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 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
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 244000205754 Colocasia esculenta Species 0.000 description 1
- 235000006481 Colocasia esculenta Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- QSBINWBNXWAVAK-PSXMRANNSA-N PE-NMe(16:0/16:0) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCNC)OC(=O)CCCCCCCCCCCCCCC QSBINWBNXWAVAK-PSXMRANNSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical class [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- PSIKPHJLTVSQFO-UHFFFAOYSA-N propanedihydrazide Chemical compound NNC(=O)CC(=O)NN PSIKPHJLTVSQFO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
- C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
-
- 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
-
- 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
-
- 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
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
-
- 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
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
- C09K2200/0647—Polyepoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nonlinear Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Sealing Material Composition (AREA)
- Liquid Crystal (AREA)
- Epoxy Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
The purpose of the present invention is to provide a sealant for a liquid crystal display element, which has excellent coating properties, moisture permeation prevention properties, and adhesion properties, and which can suppress liquid crystal contamination. Further, another object of the present invention is to provide a vertical conduction material and a liquid crystal display element using the sealant for a liquid crystal display element. The present invention is a sealant for a liquid crystal display element, comprising a curable resin, and further comprising a radical polymerization initiator and/or a thermal curing agent, wherein the curable resin comprises a compound represented by the following formula (1), the content of the compound represented by the formula (1) in the sealant for a liquid crystal display element is 1% by weight or more and less than 30% by weight, and in the formula (1), R is represented by1Is hydrogen or methyl, and m and n are each 0 to 6.
Description
Technical Field
The present invention relates to a sealant for a liquid crystal display element, which has excellent coatability, moisture permeability prevention property and adhesiveness and can suppress liquid crystal contamination. The present invention also relates to a vertical conduction material and a liquid crystal display element produced using the sealant for a liquid crystal display element.
Background
In recent years, in terms of shortening the tact time and optimizing the amount of liquid crystal used, a liquid crystal dropping method called a dropping method using a photo-thermal curing type sealing agent containing a curable resin, a photopolymerization initiator, and a thermal curing agent as disclosed in patent documents 1 and 2 has been used as a method for manufacturing a liquid crystal display element.
In the dropping process, first, a rectangular seal pattern is formed on one of 2 transparent substrates with electrodes by a dispenser. Then, in a state where the sealant is not cured, droplets of liquid crystal are dropped onto the entire surface of the frame of the transparent substrate, another transparent substrate is immediately stacked, and the sealing portion is irradiated with light such as ultraviolet rays to perform precuring. Then, the resultant was heated to perform main curing, thereby producing a liquid crystal display element. The liquid crystal display element can be manufactured with extremely high efficiency by bonding the substrates under reduced pressure, and this one drop fill process is now the mainstream of the method for manufacturing a liquid crystal display element.
However, in the modern times in which various mobile devices with liquid crystal panels, such as mobile phones and portable game machines, are widespread, the problem to be solved is the most important to miniaturize the devices. As a method for downsizing the device, narrowing of the edge of the liquid crystal display portion is exemplified, and for example, the position of the sealing portion is arranged under the black matrix (hereinafter, also referred to as narrow-edge design).
However, since the sealant is disposed directly below the black matrix in the narrow-edge design, the following problem occurs when the one-drop fill process is performed: when the sealant is photocured, the irradiated light is blocked, and the light does not reach the inside of the sealant, so that the curing is insufficient. If the curing of the sealant becomes insufficient in this way, there is a problem in that: the uncured sealant component is eluted into the liquid crystal, and a curing reaction based on the eluted sealant component proceeds in the liquid crystal, thereby causing liquid crystal contamination.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2001-133794
Patent document 2: international publication No. 02/092718
Disclosure of Invention
Problems to be solved by the invention
The purpose of the present invention is to provide a sealant for a liquid crystal display element, which has excellent coating properties, moisture permeation prevention properties, and adhesion properties, and which can suppress liquid crystal contamination. Further, another object of the present invention is to provide a vertical-conduction material and a liquid crystal display element, each of which is produced using the sealant for a liquid crystal display element.
Means for solving the problems
The present invention is a sealant for a liquid crystal display element, which contains a curable resin, and further contains a radical polymerization initiator and/or a thermal curing agent, wherein the curable resin contains a compound represented by the following formula (1), and the content of the compound represented by the formula (1) in the sealant for a liquid crystal display element is 1 wt% or more and less than 30 wt%.
[ solution 1]
In the formula (1), R1Is hydrogen or methyl, and m and n are each 0 to 6.
The present invention will be described in detail below.
The present inventors have studied to blend a bisphenol S-type epoxy resin having excellent adhesiveness and low liquid crystal contamination as a curable resin. However, even in the case of using a bisphenol S type epoxy resin, there are the following problems: the effect of suppressing liquid crystal contamination is insufficient, or the obtained sealant for a liquid crystal display element is inferior in coatability and moisture permeation resistance.
The present inventors have found that a sealant for a liquid crystal display element, which is excellent in coatability, moisture permeability prevention property and adhesiveness and can suppress contamination of liquid crystal, can be obtained by blending a specific amount of a specific compound having a bisphenol S type structure, and have completed the present invention.
The sealant for a liquid crystal display element of the present invention contains a curable resin.
The curable resin contains a compound represented by the formula (1). By containing the compound represented by the formula (1), the sealant for a liquid crystal display element of the present invention is excellent in adhesiveness and an effect of suppressing liquid crystal contamination.
In the formula (1), m and n are each 0 to 6. M and n are preferably 1 to 6, and more preferably 1 to 3, respectively.
In the above formula (1) and the formula (2) described later, the values of m and n are average values. When m and n are 0, the ethylene oxide moiety having m and n is a bond.
Examples of the method for producing the compound represented by the formula (1) include the following methods: a method in which bisphenol S or ethylene oxide-added bisphenol S is reacted with epichlorohydrin to produce a compound represented by the following formula (2), and one epoxy group of the resulting compound represented by the formula (2) is reacted with (meth) acrylic acid.
In the present specification, the term "(meth) acrylic acid" refers to acrylic acid and/or methacrylic acid.
[ solution 2]
In the formula (2), m and n are each 0 to 6.
The content of the compound represented by the formula (1) in the sealant for a liquid crystal display element of the present invention is 1% by weight or more and less than 30% by weight. If the content of the compound represented by the above formula (1) is less than 1% by weight, the obtained sealant for a liquid crystal display element tends to be a sealant having poor adhesiveness. When the content of the compound represented by the formula (1) is 30% by weight or more, the obtained sealant for a display element is poor in coatability and moisture permeability resistance. The content of the compound represented by the above formula (1) has a preferable lower limit of 5% by weight, a preferable upper limit of 25% by weight, a more preferable lower limit of 10% by weight, a still more preferable upper limit of 20% by weight, and a still more preferable upper limit of 15% by weight.
The curable resin preferably contains another curable resin in addition to the compound represented by the formula (1).
Examples of the other curable resin include a (meth) acrylic compound and an epoxy compound other than the compound represented by the formula (1). Among these, (meth) acrylic compounds preferably contain epoxy (meth) acrylate described later, and more preferably resorcinol type epoxy (meth) acrylate.
In the present specification, the term "(meth) acrylate" refers to acrylate or methacrylate, and the term "epoxy (meth) acrylate" refers to a compound obtained by reacting all epoxy groups in an epoxy compound with (meth) acrylic acid.
Examples of the (meth) acrylic compound of the other curable resin include epoxy (meth) acrylate obtained by reacting (meth) acrylic acid with an epoxy compound, (meth) acrylate compound obtained by reacting a compound having a hydroxyl group with (meth) acrylic acid, urethane (meth) acrylate obtained by reacting a (meth) acrylic acid derivative having a hydroxyl group with an isocyanate compound, and epoxy (meth) acrylate is preferable as described above. In addition, the (meth) acrylic compound is preferably a compound having 2 or more (meth) acryloyl groups in the molecule, from the viewpoint of high reactivity.
Examples of the epoxy (meth) acrylate include: epoxy (meth) acrylates obtained by reacting an epoxy compound with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
Examples of the epoxy compound to be used as a raw material for synthesizing the above epoxy (meth) acrylate include bisphenol a type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, 2' -diallylbisphenol a type epoxy resin, hydrogenated bisphenol type epoxy resin, propylene oxide-adduct bisphenol a type epoxy resin, m-phenylene bisphenol type epoxy resin, biphenyl type epoxy resin, thioether type epoxy resin, diphenylether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol novolac type epoxy resin, o-cresol novolac type epoxy resin, dicyclopentadiene novolac type epoxy resin, biphenyl novolac type epoxy resin, naphthol novolac type epoxy resin, glycidylamine type epoxy resin, alkyl polyhydric alcohol type epoxy resin, naphthol novolac type epoxy resin, phenol novolac amine type epoxy resin, alkyl polyhydric alcohol type epoxy resin, and the like, Rubber-modified epoxy resins, glycidyl ester compounds, and the like. Among them, resorcinol type epoxy resins are preferable.
Examples of commercially available products of the bisphenol A epoxy resin include jER828EL, jER1004 (both manufactured by Mitsubishi chemical corporation), Epiclon 850CRP (manufactured by DIC corporation), and the like.
Examples of commercially available products of the bisphenol F type epoxy resin include jER806 and jER4004 (both manufactured by Mitsubishi chemical corporation).
Examples of commercially available products of the bisphenol E epoxy resin include R710 (manufactured by Printec).
Examples of commercially available products of the bisphenol S epoxy resin include Epiclon EXA1514 (available from DIC).
Examples of commercially available products of the 2, 2' -diallylbisphenol A-type epoxy resin include RE-810NM (manufactured by Nippon chemical Co., Ltd.).
Examples of commercially available products of the hydrogenated bisphenol epoxy resin include Epiclon EXA7015 (available from DIC corporation).
Examples of commercially available products of the above propylene oxide-added bisphenol A epoxy resin include EP-4000S (manufactured by ADEKA).
Examples of commercially available products of the above resorcinol type epoxy resins include EX-201 (manufactured by Nagase ChemteX).
Examples of the products commercially available from the biphenyl type epoxy resins include jER YX-4000H (manufactured by Mitsubishi chemical corporation).
Examples of commercially available products of the thioether-type epoxy resin include YSLV-50 TE (manufactured by Nippon Tekken chemical Co., Ltd.).
Examples of commercially available products of the above diphenyl ether type epoxy resins include YSLV-80DE (manufactured by Nippon Tekken chemical Co., Ltd.).
Examples of commercially available products of the above-mentioned dicyclopentadiene type epoxy resin include EP-4088S (manufactured by ADEKA).
Examples of commercially available products of the naphthalene epoxy resin include Epiclon HP4032 and Epiclon EXA-4700 (both available from DIC).
Examples of commercially available products of the phenol novolac epoxy resins include Epiclon N-770 (available from DIC).
Examples of commercially available products of the above o-cresol novolac type epoxy resin include Epiclon N-670-EXP-S (available from DIC).
Examples of commercially available products of the dicyclopentadiene novolac type epoxy resin include Epiclon HP7200 (available from DIC).
Examples of the commercially available products of the above biphenyl novolak type epoxy resin include NC-3000P (manufactured by Nippon chemical Co., Ltd.).
Examples of commercially available products of the naphthol novolac type epoxy resins include ESN-165S (manufactured by Nippon iron Co., Ltd.).
Examples of commercially available products of the glycidyl amine type epoxy resin include JeR630 (manufactured by Mitsubishi chemical corporation), Epiclon 430 (manufactured by DIC corporation), and TETRAD-X (manufactured by Mitsubishi gas chemical corporation).
Examples of commercially available products of the above-mentioned alkyl polyol type epoxy resin include ZX-1542 (manufactured by Nippon Tekken chemical Co., Ltd.), Epiclon 726 (manufactured by DIC Co., Ltd.), Epolite 80MFA (manufactured by Kyoho chemical Co., Ltd.), and Denacol EX-611 (manufactured by Nagase ChemteX Co., Ltd.).
Examples of commercially available products of the rubber-modified epoxy resin include YR-450, YR-207 (both manufactured by Nippon Tekken chemical Co., Ltd.), and Epolide PB (manufactured by Daiiol Co., Ltd.).
Examples of commercially available products of the glycidyl ester compounds include Denacolex-147 (manufactured by Nagase ChemteX).
Examples of other commercially available products of the above epoxy compounds include: YDC-1312, YSLV-80XY and YSLV-90CR (all manufactured by Nissi iron-on-gold chemical Co., Ltd.); XAC4151 (manufactured by Asahi Kasei corporation); jER1031 and jER1032 (both manufactured by Mitsubishi chemical corporation); EXA-7120 (manufactured by DIC corporation); TEPIC (manufactured by Nissan chemical Co., Ltd.), and the like.
Examples of commercially available products of the above epoxy (meth) acrylates include: EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3708, EBECRYL3800, EBECRYL6040, and EBECRYLRDX63182 (both manufactured by DAICEL-ALLNEX Co., Ltd.); EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (all manufactured by Xinzhongcun chemical industry Co., Ltd.); 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 (all manufactured by Kyoeisha chemical Co., Ltd.); denacol ACRYLATE DA-141, Denacol ACRYLATE DA-314, Denacol ACRYLATE DA-911 (all manufactured by Nagase ChemteX Co., Ltd.), and the like.
Examples of the monofunctional (meth) acrylate compound in the above-mentioned (meth) acrylate compound include: methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, n-butyl (, Benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, ethylcarbitol (meth) acrylate, 2, 2, 2-trifluoroethyl (meth) acrylate, 2, 2, 3, 3-tetrafluoropropyl (meth) acrylate, 1H, 5H-octafluoropentyl (meth) acrylate, imide (meth) acrylate, dimethylaminoethyl (meth) acrylate, N-butylaminoethyl (meth, Diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethylsuccinic acid, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxyethyl 2-hydroxypropylphthalate, 2- (meth) acryloyloxyethyl phosphate, glycidyl (meth) acrylate, and the like.
Examples of the 2-functional (meth) acrylate compound in the above-mentioned (meth) acrylate compounds include 1, 3-butanediol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, 1, 10-decanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 2-n-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, and mixtures thereof, Polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide-added bisphenol a di (meth) acrylate, propylene oxide-added bisphenol a di (meth) acrylate, ethylene oxide-added bisphenol F di (meth) acrylate, dimethylol dicyclopentadiene di (meth) acrylate, ethylene oxide-modified isocyanuric acid di (meth) acrylate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, carbonate diol di (meth) acrylate, polyether diol di (meth) acrylate, polyester diol di (meth) acrylate, polycaprolactone diol di (meth) acrylate, polybutylene glycol di (meth) acrylate, and the like.
In addition, as the (meth) acrylate compound having 3 or more functions among the above (meth) acrylate compounds, there can be mentioned, for example: trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, glycerin tri (meth) acrylate, propylene oxide-added glycerin tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tri (meth) acryloyloxyethyl phosphate, ditrimethylol propane tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.
The urethane (meth) acrylate can be obtained, for example, by reacting 1 equivalent of an isocyanate compound having 2 isocyanate groups with 2 equivalents of a (meth) acrylic acid derivative having a hydroxyl group in the presence of a catalytic amount of a tin-based compound.
Examples of the isocyanate compound which is a raw material of the urethane (meth) acrylate include isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4, 4' -diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, Xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethylxylene diisocyanate, 1, 6, 11-undecane triisocyanate, and the like.
As the isocyanate compound which is a raw material of the urethane (meth) acrylate, for example, a chain-extended isocyanate compound obtained by reacting a polyol such as ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol, or the like with an excessive amount of an isocyanate compound may be used.
Examples of the (meth) acrylic acid derivative having a hydroxyl group which is a raw material of the urethane (meth) acrylate include: hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate; mono (meth) acrylates of dihydric alcohols such as ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 3-butanediol, 1, 4-butanediol, and polyethylene glycol; mono (meth) acrylate or di (meth) acrylate of trihydric alcohols such as trimethylolethane, trimethylolpropane and glycerol; epoxy (meth) acrylates such as bisphenol a type epoxy acrylates, and the like.
Examples of commercially available products of the urethane (meth) acrylates include: m-1100, M-1200, M-1210 and M-1600 (all manufactured by Toyo synthetic company); EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270, EBECRYL1290, EBECRYL2220, EBECRYL4827, EBECRYL4842, EBECRYL4858, EBECRYL5129, EBECRYL6700, EBECRYL8402, EBECRYL8803, EBECRYL8804, EBECRYL8807, EBECRYL9260 (all available from DAICEL-ALLNEX Co., Ltd.); 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 and Art Resin UN-9000H (all manufactured by Kokai Co., Ltd.); u-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6HA, U-6 LPA, U-10H, U-15HA, 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 and UA-W2A (all manufactured by Ninghamun chemical industry Co., Ltd.); AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (all manufactured by Kyoeisha chemical Co., Ltd.), and the like.
Examples of the epoxy compound of the other curable resin include: an epoxy compound which becomes a raw material for synthesizing the epoxy (meth) acrylate; and (meth) acrylic-modified epoxy resins other than the compound represented by the formula (1).
In the present specification, the partially (meth) acrylic-modified epoxy resin is a compound having 1 or more epoxy groups and 1 or more (meth) acryloyl groups in each molecule, and can be obtained by, for example, reacting a part of the epoxy groups of 2 or more epoxy compounds with (meth) acrylic acid.
Examples of the product sold in the partially (meth) acrylic-modified epoxy resin include UVACURE1561 (manufactured by DAICEL-ALLNEX).
When the other curable resin is contained, the content of the compound represented by the formula (1) in 100 parts by weight of the total curable resin preferably has a lower limit of 5 parts by weight and an upper limit of 25 parts by weight. By setting the content of the compound represented by the above formula (1) within this range, the obtained sealant for a liquid crystal display element has more excellent coatability, adhesiveness, moisture permeation prevention and liquid crystal contamination suppression effects. A more preferable lower limit of the content of the compound represented by the above formula (1) is 10 parts by weight, and a more preferable upper limit is 20 parts by weight.
The sealant for a liquid crystal display element of the present invention preferably has a molar ratio of the (meth) acryloyl group to the epoxy group in the curable resin of 50: 50 to 95: 5.
The sealant for a liquid crystal display element of the present invention contains a radical polymerization initiator and/or a thermal curing agent.
Examples of the radical polymerization initiator include a photo radical polymerization initiator which generates radicals by irradiation with light, a thermal radical polymerization initiator which generates radicals by heating, and the like.
Examples of the photo radical polymerization initiator include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, and thioxanthone compounds.
Examples of commercially available products of the photo radical polymerization initiator include: IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE OXE01, and Lucirin TPO (all manufactured by BASF corporation); NCI-930 (manufactured by ADEKA corporation); SPEEDCURE EMK (manufactured by Nippon Siberhegner Co., Ltd.); benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (all manufactured by Tokyo chemical industries Co., Ltd.), and the like.
Examples of the thermal radical polymerization initiator include thermal radical polymerization initiators formed from azo compounds, organic peroxides, and the like. Among them, an initiator formed of a polymeric azo compound (hereinafter, also referred to as "polymeric azo initiator") is preferable.
In the present specification, the macromolecular azo compound means: a compound having an azo group and capable of thermally generating a radical capable of curing a (meth) acryloyl group, the compound having a number average molecular weight of 300 or more.
The number average molecular weight of the polymeric azo initiator preferably has a lower limit of 1000 and an upper limit of 30 ten thousand. When the number average molecular weight of the polymeric azo initiator is in this range, liquid crystal contamination can be suppressed and the azo initiator can be easily mixed with a curable resin. A more preferable lower limit of the number average molecular weight of the polymeric azo initiator is 5000, a more preferable upper limit is 10 ten thousand, a further more preferable lower limit is 1 ten thousand, and a further more preferable upper limit is 9 ten thousand.
In the present specification, the number average molecular weight is a value measured by Gel Permeation Chromatography (GPC) and obtained based on polystyrene conversion. Examples of the column for measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko K.K.).
Examples of the polymeric azo initiator include polymeric azo initiators having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via an azo group.
The polymer azo initiator having a structure in which a plurality of units such as polyalkylene oxide are bonded via an azo group is preferably a polymer azo initiator having a polyethylene oxide structure. Examples of such a polymeric azo initiator include a polycondensate of 4, 4 '-azobis (4-cyanovaleric acid) and a polyalkylene glycol and a polycondensate of 4, 4' -azobis (4-cyanovaleric acid) and a polydimethylsiloxane having a terminal amino group, and specifically include VPE-0201, VPE-0401, VPE-0601, VPS-0501 and VPS-1001 (both manufactured by Wako pure chemical industries, Ltd.).
Further, examples of azo compounds which are not polymers include V-65 and V-501 (both manufactured by Wako pure chemical industries, Ltd.).
Examples of the organic peroxide include ketone peroxide, peroxyketal, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
The lower limit of the content of the radical polymerization initiator is preferably 0.01 part by weight and the upper limit is preferably 10 parts by weight with respect to 100 parts by weight of the curable resin. When the content of the radical polymerization initiator is in this range, the obtained sealant for a liquid crystal display element is more excellent in storage stability and curability while suppressing contamination of liquid crystal. A more preferable lower limit of the content of the self-radical polymerization initiator is 0.1 part by weight, and a more preferable upper limit is 5 parts by weight.
Examples of the heat-curing agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyphenol compounds, and acid anhydrides. Among them, organic acid hydrazide is preferably used.
Examples of the organic acid hydrazide include sebacic dihydrazide, isophthalic dihydrazide, adipic dihydrazide, malonic dihydrazide, and the like.
Examples of commercially available products of the organic acid hydrazide include SDH, ADH (available from Otsuka chemical Co., Ltd.), AMICURE VDH-J, AMICURE UDH and AMICURE UDH-J (available from Ajinomoto Fine-Techno Co., Ltd.).
The lower limit of the content of the heat-curing agent is preferably 1 part by weight, and the upper limit is preferably 50 parts by weight, based on 100 parts by weight of the curable resin. By setting the content of the thermosetting agent in this range, the thermosetting property can be further improved without deteriorating the coating property and the like of the obtained sealant for a liquid crystal display element. A more preferable upper limit of the content of the thermosetting agent is 30 parts by weight.
The sealant for a liquid crystal display element of the present invention preferably contains a filler for the purpose of increasing viscosity, improving adhesiveness by a stress dispersion effect, improving a linear expansion coefficient, improving moisture permeation resistance of a cured product, and the like.
Examples of the filler include: inorganic fillers such as silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, smectite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium hydroxide, aluminum nitride, silicon nitride, barium sulfate, and calcium silicate; organic fillers such as polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles.
The lower limit of the content of the filler in the sealant for a liquid crystal display element of the present invention is preferably 10% by weight, and the upper limit is preferably 70% by weight. By setting the content of the filler within this range, the effects of improving the adhesiveness and the like can be further improved without deteriorating the coating property and the like. The lower limit of the content of the filler is more preferably 20% by weight, and the upper limit is more preferably 60% by weight.
The sealant for a liquid crystal display element of the present invention preferably contains a silane coupling agent. The silane coupling agent mainly functions as an adhesion aid for satisfactorily adhering the sealant to a substrate or the like.
The silane coupling agent is preferably used, for example, as 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane or the like, because it has an excellent effect of improving the adhesion to a substrate or the like and can inhibit the outflow of a curable resin into a liquid crystal by chemically bonding to the curable resin.
The lower limit of the content of the silane coupling agent in the sealant for a liquid crystal display element of the present invention is preferably 0.1% by weight, and the upper limit is preferably 10% by weight. When the content of the silane coupling agent is in this range, the effect of improving the adhesiveness is further enhanced while the occurrence of liquid crystal contamination is suppressed. A more preferable lower limit of the content of the silane coupling agent is 0.3 wt%, and a more preferable upper limit is 5 wt%.
The sealant for a liquid crystal display element of the present invention may contain a light-shading agent. By containing the light-shading agent, the sealant for a liquid crystal display element of the present invention can be suitably used as a light-shading sealant.
Examples of the light-shading agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Among them, titanium black is preferable.
The titanium black has a higher transmittance for light in the vicinity of an ultraviolet region, particularly 370 to 450nm, than the average transmittance for light having a wavelength of 300 to 800 nm. That is, the titanium black is a light-shielding agent which sufficiently shields light having a wavelength in the visible light region to impart light-shielding properties to the sealant for a liquid crystal display element of the present invention and has a property of transmitting light having a wavelength in the vicinity of the ultraviolet region. The light-shading agent contained in the sealant for a liquid crystal display element of the present invention is preferably a high-insulating material, and titanium black is also suitable as a high-insulating light-shading agent.
The titanium black exhibits sufficient effects without being surface-treated, and the following may be used: titanium black having a surface treated with an organic component such as a coupling agent; titanium black having a surface treated with titanium black or the like coated with an inorganic component such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, magnesium oxide, or the like. Among them, titanium black treated with an organic component is preferable in terms of further improving the insulation property.
Further, since the liquid crystal display element produced using the sealant for a liquid crystal display element of the present invention containing the titanium black as a light-shielding agent has sufficient light-shielding properties, a liquid crystal display element having high contrast and excellent image display quality without light leakage can be realized.
Examples of commercially available products of the above titanium black include 12S, 13M-C, 13R-N, 14M-C (both manufactured by Mitsubishi Materials Co., Ltd.), and Tilack D (manufactured by Red spicing chemical Co., Ltd.).
The lower limit of the specific surface area of the titanium black is preferably 13m2A preferred upper limit of 30m2A more preferred lower limit is 15m2In terms of/g, more preferably aboveLimit of 25m2/g。
The volume resistance of the titanium black has a preferred lower limit of 0.5 Ω · cm and a preferred upper limit of 3 Ω · cm, and a more preferred lower limit of 1 Ω · cm and a more preferred upper limit of 2.5 Ω · cm.
The primary particle size of the light-shading agent is not particularly limited as long as it is not more than the distance between substrates of the liquid crystal display device, but a preferable lower limit is 1nm and a preferable upper limit is 5000 nm. By setting the primary particle size of the light-shielding agent in this range, the light-shielding property can be further improved without deteriorating the coatability and the like of the obtained sealant for a liquid crystal display element. The lower limit of the primary particle diameter of the light-shading agent is preferably 5nm, the upper limit thereof is preferably 200nm, the lower limit thereof is preferably 10nm, and the upper limit thereof is preferably 100 nm.
The primary PARTICLE size of the light-shading agent can be measured by dispersing the light-shading agent in a solvent (such as water or an organic solvent) using NICOMP 380ZLS (manufactured by part SIZING SYSTEMS).
The content of the light-shading agent in the sealant for a liquid crystal display element of the present invention has a preferable lower limit of 5% by weight and a preferable upper limit of 80% by weight. By setting the content of the light-shading agent within this range, it is possible to exhibit more excellent light-shading properties without deteriorating the adhesion of the obtained sealant for a liquid crystal display element to a substrate, the strength after curing, and the drawing properties. The lower limit of the content of the light-shading agent is more preferably 10% by weight, the upper limit is more preferably 70% by weight, the lower limit is more preferably 30% by weight, and the upper limit is more preferably 60% by weight.
The sealant for a liquid crystal display element of the present invention may further contain a stress relaxation agent, a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, a defoaming agent, a leveling agent, a polymerization inhibitor, other additives, and the like as required.
Examples of the method for producing the sealant for a liquid crystal display element of the present invention include: a method of mixing the curable resin, the polymerization initiator and/or the thermosetting agent, and if necessary, additives such as a silane coupling agent, using a mixer such as a homomixer, universal mixer, planetary mixer, kneader, or three-roll mill.
The sealant for a liquid crystal display element of the present invention has a preferable lower limit of 5 ten thousand mPas and a preferable upper limit of 70 ten thousand mPas, which are measured at 25 ℃ and 1rpm with an E-type viscometer. When the viscosity is within this range, the resulting sealant for a liquid crystal display element has excellent coatability. A more preferable lower limit of the viscosity is 10 ten thousand mPas, and a more preferable upper limit is 50 ten thousand mPas.
As the E-type viscometer, 5XHBDV-III + CP (Brookfield, spindle No. CP-51) or the like can be used, for example.
By incorporating conductive fine particles into the sealant for a liquid crystal display element of the present invention, a vertical conduction material can be produced. The vertical conduction material comprising the sealant for liquid crystal display element of the present invention and conductive fine particles is also one aspect of the present invention.
As the conductive fine particles, metal balls, conductive fine particles in which a conductive metal layer is formed on the surface of resin fine particles, or the like can be used. Among these, the conductive fine particles having the conductive metal layer formed on the surface of the resin fine particles are preferable because the resin fine particles have excellent elasticity and can be electrically connected without damaging the transparent substrate or the like.
A liquid crystal display element produced using the sealant for a liquid crystal display element of the present invention or the vertical conduction material of the present invention is also one aspect of the present invention.
As a method for manufacturing the liquid crystal display element of the present invention, a liquid crystal dropping process is suitably used. Specifically, for example, a method including the following steps: a step of forming a frame-shaped seal pattern by applying the sealant for a liquid crystal display element of the present invention on one of 2 substrates such as a glass substrate with an electrode such as an ITO film and a polyethylene terephthalate substrate by screen printing, dispenser application, or the like; a step of applying a fine droplet of liquid crystal dropwise into a frame of a seal pattern of a substrate in an uncured state of the sealant for a liquid crystal display element of the present invention, and superposing another substrate under vacuum; a step of irradiating a seal pattern portion of the sealant for a liquid crystal display element of the present invention with light such as ultraviolet rays to precure the sealant; and a step of heating the precured sealant to cure it mainly.
Effects of the invention
The present invention can provide a sealant for a liquid crystal display element which has excellent coatability, moisture permeation prevention, and adhesiveness and can suppress contamination of liquid crystal. Further, according to the present invention, a vertical conduction material and a liquid crystal display element, which are produced using the sealant for a liquid crystal display element, can be provided.
Detailed Description
The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
(Compound (R) represented by the formula (1)1Manufactured for H, m ═ n ═ 0)
While feeding air, 1000 parts by weight of bisphenol S diglycidyl ether, 2 parts by weight of p-methoxyphenol as a polymerization inhibitor, 2 parts by weight of triethylamine as a reaction catalyst, and 200 parts by weight of acrylic acid were refluxed and stirred at 90 ℃ for 5 hours to react. 100 parts by weight of the obtained resin was filtered through a column packed with 10 parts by weight of a natural combination of quartz and kaolin (product of Hoffmann Mineral, Silitin V85) for adsorbing ionic impurities in the reaction product, to obtain a compound represented by formula (1) (R)1H, m ═ n ═ 0). To explain, utilize1H-NMR、13C-NMR and IR confirmed that the obtained compound was a compound (R) represented by the formula (1)1H, m ═ n ═ 0).
(Compound (R) represented by the formula (1)1Manufactured for H, m ═ n ═ 1 (average)))
A flask equipped with a thermometer, a dropping funnel, a condenser and a stirrer was charged with 169 parts by weight of 4, 4' -bis (2-hydroxyethyloxy) diphenylsulfone, 370 parts by weight of epichlorohydrin, 185 parts by weight of dimethyl sulfoxide and 5 parts by weight of tetramethylammonium chloride, and the mixture was dissolved with stirring and heated to 50 ℃. Then, the flakes are added in portions over 100 minutesAfter 60 parts by weight of sodium hydroxide, the reaction was further carried out at 50 ℃ for 3 hours. After the reaction, 400 parts by weight of water was added thereto to wash with water, and excess epichlorohydrin and the like were distilled off from the oil layer at 130 ℃ under reduced pressure using a rotary evaporator. To the residue was added 450 parts by weight of methyl isobutyl ketone to dissolve it, and the temperature was raised to 70 ℃. 10 parts by weight of a 30% aqueous solution of sodium hydroxide was added thereto under stirring to carry out a reaction for 1 hour, followed by 3 times of water washing, and then methyl isobutyl ketone was distilled off at 180 ℃ under reduced pressure using a rotary evaporator. While feeding air, 1100 parts by weight of the obtained reactant, 2 parts by weight of p-methoxyphenol as a polymerization inhibitor, 2 parts by weight of triethylamine as a reaction catalyst, and 200 parts by weight of acrylic acid were refluxed and stirred at 90 ℃ for 5 hours to react. 100 parts by weight of the obtained resin was filtered through a column packed with 10 parts by weight of a natural combination of quartz and kaolin (product of Hoffmann Mineral, "Silitin V85") to adsorb ionic impurities in the reaction product, to obtain a compound represented by formula (1) (R)1The value H, m ═ n ═ 1 (average)). To explain, utilize1H-NMR、13The obtained compound was confirmed by C-NMR and IR to be a compound represented by formula (1) (R1 was H, m ═ n ═ 1 (average value)).
(examples 1 to 7 and comparative examples 1 to 4)
The respective materials were mixed with a planetary mixer (a "zabba taro" manufactured by THINKY corporation) at the mixing ratios shown in table 1, and then mixed with a three-roll mixer, thereby preparing the respective liquid crystal display element sealants of examples 1 to 7 and comparative examples 1 to 4.
< evaluation >
The following evaluations were performed on the liquid crystal display element sealants obtained in examples and comparative examples. The results are shown in Table 1.
(coatability)
The liquid crystal display elements obtained in examples and comparative examples were each coated with a sealant on a glass substrate using a dispenser (manufactured by Musashi Engineering corporation, "SHOTMASTER 300"). When the dispenser nozzle was fixed at 400 μm, the nozzle gap was fixed at 30 μm, and the coating pressure was fixed at 300kPa for coating, the coating performance was evaluated by assuming "excellent" when the coating was possible without abrasion or tear drop, "good" when the coating was generated with slight abrasion or tear drop, "Δ" when the coating was not broken but large abrasion or tear drop was generated, and "x" when the coating was broken or completely impossible.
(adhesiveness)
1 part by weight of spacer particles having an average particle diameter of 5 μm (Micro-Pearl SP-2050, manufactured by Sekish chemical industries, Ltd.) was uniformly dispersed using a planetary stirring device per 100 parts by weight of each of the liquid crystal display element sealants obtained in examples and comparative examples, and a trace amount of the spacer particles was taken up to a central portion of Corning glass 1737(20 mm. times.50 mm. times.0.7 mm in thickness), and the same type of glass was superimposed on the central portion, and the sealant for liquid crystal display elements was spread, and irradiated with a metal halide lamp for 30 seconds at 100mW/cm2After the UV irradiation, the sealant was cured by heating at 120 ℃ for 1 hour to obtain an adhesion test piece.
The adhesion strength of the obtained adhesion test piece was measured using a tensiometer. The obtained measurement value (kgf) was divided by the seal coating cross-sectional area (cm)2) The obtained value was 35kgf/cm2The value is defined as ". circinata" and is 30kgf/cm2Above and below 35kgf/cm2When the measured value is "O", the value is 250kgf/cm2Above and below 30kgf/cm2The value of (A) is represented by "Delta", and the value is less than 25kgf/cm2The case of (2) was represented by "x", and adhesiveness was evaluated.
(moisture permeability prevention)
Each of the sealants for liquid crystal display elements obtained in examples and comparative examples was applied in a thickness of 200 to 300 μm to a smooth release film by a coater, and then irradiated with a metal halide lamp for 30 seconds at a rate of 100mW/cm2And then heated at 120 ℃ for 1 hour to obtain a cured film for moisture permeability measurement.
A cup for moisture permeability test was prepared by the method of moisture permeability test method (cup method) of moisture-proof packaging material based on JIS Z0208, the obtained cured film for moisture permeability measurement was mounted, and the cup was put into warm airThe moisture permeability was measured in a constant temperature and humidity oven at 80 ℃ and a humidity of 90% RH. The obtained value of moisture permeability is less than 60g/m2"in the case of 24 hr", the value of the obtained moisture permeability is 60g/m 2-24 hr or more and less than 100g/m2When 24hr was used, the value was defined as ". smallcircle", and the obtained moisture permeability was defined as 100g/m224hr or more and less than 120g/m2"Δ" in the case of 24hr, and the resulting value of the moisture permeability was set to 120g/m2The case of 24hr or more was "x", and the moisture permeability resistance was evaluated.
(display Performance of liquid Crystal display element (Low liquid Crystal contamination))
1 part by weight of spacer particles having an average particle diameter of 5 μm (Micro-Pearl SP-2050, manufactured by waterlogging chemical industries, Ltd.) was uniformly dispersed with a planetary stirring apparatus per 100 parts by weight of each of the sealants for liquid crystal display elements obtained in examples and comparative examples, and the resulting sealant was filled into a syringe for dispensing (PS Y-10E, manufactured by Musashi Engineering, Ltd.) and subjected to a defoaming treatment, and then the sealant was applied in a frame shape to one of 2 transparent electrode substrates with an ITO film with a dispenser (shotmas 300, manufactured by Musashi Engineering, Ltd.). Subsequently, minute droplets of TN liquid crystal (JC-5001 LA, manufactured by Chisso corporation) were applied dropwise into the frame of the sealant by a liquid crystal dropping device, and the other transparent substrate was bonded under vacuum of 5Pa by a vacuum bonding device to obtain a cell. The resulting unit was irradiated with a metal halide lamp for 30 seconds at 100mW/cm2And then heated at 120 ℃ for 1 hour to cure the sealant, thereby obtaining a liquid crystal display element.
The obtained liquid crystal display element was evaluated for display performance (low liquid crystal contamination) by visually observing display unevenness occurring in the liquid crystal (particularly, corner portions) around the seal portion, assuming that "excellent" was observed when no display unevenness was observed, assuming that "o" was observed when slight display unevenness was observed, assuming that "Δ" was observed when clear display unevenness was observed, and assuming that "x" was observed when severe display unevenness was observed.
Note that the liquid crystal display elements evaluated as "cyaro" and "∘" were all of a level which has no problem in practical use.
[ Table 1]
Industrial applicability
The present invention can provide a sealant for a liquid crystal display element which has excellent coatability, moisture permeation prevention, and adhesiveness and can suppress contamination of liquid crystal. Further, according to the present invention, a vertical conduction material and a liquid crystal display element, which are produced using the sealant for a liquid crystal display element, can be provided.
Claims (4)
1. A sealant for a liquid crystal display element, which comprises a curable resin and further comprises a radical polymerization initiator and/or a thermal curing agent,
the curable resin contains a compound represented by the following formula (1),
the content of the compound represented by the formula (1) in the sealant for a liquid crystal display element is 1% by weight or more and less than 30% by weight,
in the formula (1), R1Is hydrogen or methyl, and m and n are each 0 to 6.
2. The sealant for a liquid crystal display element according to claim 1, wherein the curable resin further contains an epoxy (meth) acrylate.
3. A vertically conducting material comprising the sealant for liquid crystal display element according to claim 1 or 2 and conductive fine particles.
4. A liquid crystal display element produced by using the sealant for a liquid crystal display element according to claim 1 or 2 or the vertically conducting material according to claim 3.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016001915 | 2016-01-07 | ||
| JP2016-001915 | 2016-01-07 | ||
| PCT/JP2017/000004 WO2017119406A1 (en) | 2016-01-07 | 2017-01-04 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107636524A CN107636524A (en) | 2018-01-26 |
| CN107636524B true CN107636524B (en) | 2021-07-06 |
Family
ID=59274206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201780001784.1A Active CN107636524B (en) | 2016-01-07 | 2017-01-04 | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP6798978B2 (en) |
| KR (1) | KR20180100473A (en) |
| CN (1) | CN107636524B (en) |
| TW (1) | TWI707946B (en) |
| WO (1) | WO2017119406A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6653305B2 (en) * | 2017-11-10 | 2020-02-26 | 日本ユピカ株式会社 | Crystalline radical polymerizable composition for electric / electronic parts, molded article of electric / electronic part using the composition, and method for producing molded article of electric / electronic part |
| CN110382560A (en) * | 2017-03-03 | 2019-10-25 | 日本优必佳株式会社 | Electrical/electronic part crystallinity radical-polymerizable composition uses the electrical/electronic part formed body of the composition and the manufacturing method of the electrical/electronic part formed body |
| JP6630695B2 (en) * | 2017-03-03 | 2020-01-15 | 日本ユピカ株式会社 | Crystalline radical polymerizable composition for sealing electric and electronic parts, sealed body for electric and electronic parts using the composition, and method for producing the sealed body |
| KR20210012994A (en) * | 2018-05-25 | 2021-02-03 | 세키스이가가쿠 고교가부시키가이샤 | Liquid crystal display element sealing agent, upper and lower conduction material and liquid crystal display element |
| KR20210098945A (en) * | 2018-12-07 | 2021-08-11 | 세키스이가가쿠 고교가부시키가이샤 | Sealing agent for display elements, hardened|cured material, vertical conduction material, and display element |
| EP4119589A1 (en) * | 2021-07-16 | 2023-01-18 | Hilti Aktiengesellschaft | Epoxy resin mixtures comprising epoxide-acrylate hybrid molecules and multicomponent reactive resin compositions therefrom |
| EP4119590A1 (en) * | 2021-07-16 | 2023-01-18 | Hilti Aktiengesellschaft | Epoxide-acrylate hybrid molecules and their use for chemical anchoring |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1388143A (en) * | 2001-05-16 | 2003-01-01 | 味之素株式会社 | Potential curing agent for epoxy resin solidified epoxy resin composition |
| TW201124783A (en) * | 2009-10-02 | 2011-07-16 | Sekisui Chemical Co Ltd | Method for manufacturing liquid crystal display device |
| TW201506137A (en) * | 2013-06-11 | 2015-02-16 | Sekisui Chemical Co Ltd | Sealing agent for liquid crystal dropping methods, vertically conducting material, and liquid crystal display element |
| WO2015178357A1 (en) * | 2014-05-23 | 2015-11-26 | 積水化学工業株式会社 | Sealant for one-drop filling process, vertically conductive material, and liquid crystal display element |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3583326B2 (en) | 1999-11-01 | 2004-11-04 | 協立化学産業株式会社 | Sealant for dripping method of LCD panel |
| WO2002092718A1 (en) | 2001-05-16 | 2002-11-21 | Sekisui Chemical Co., Ltd. | Curing resin composition and sealants and end-sealing materials for displays |
| US7521099B2 (en) * | 2004-09-06 | 2009-04-21 | Nippon Kayaku Kabushiki Kaisha | Liquid crystal sealing material and liquid crystal display cell using same |
| EP1932894A1 (en) * | 2005-09-02 | 2008-06-18 | Dainippon Ink And Chemicals, Inc. | Photocurable composition for sealing agent, liquid crystal sealing agent, and liquid crystal panel |
-
2016
- 2016-12-29 TW TW105143879A patent/TWI707946B/en active
-
2017
- 2017-01-04 JP JP2017502913A patent/JP6798978B2/en active Active
- 2017-01-04 WO PCT/JP2017/000004 patent/WO2017119406A1/en active Application Filing
- 2017-01-04 KR KR1020177035070A patent/KR20180100473A/en not_active Application Discontinuation
- 2017-01-04 CN CN201780001784.1A patent/CN107636524B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1388143A (en) * | 2001-05-16 | 2003-01-01 | 味之素株式会社 | Potential curing agent for epoxy resin solidified epoxy resin composition |
| TW201124783A (en) * | 2009-10-02 | 2011-07-16 | Sekisui Chemical Co Ltd | Method for manufacturing liquid crystal display device |
| TW201506137A (en) * | 2013-06-11 | 2015-02-16 | Sekisui Chemical Co Ltd | Sealing agent for liquid crystal dropping methods, vertically conducting material, and liquid crystal display element |
| WO2015178357A1 (en) * | 2014-05-23 | 2015-11-26 | 積水化学工業株式会社 | Sealant for one-drop filling process, vertically conductive material, and liquid crystal display element |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20180100473A (en) | 2018-09-11 |
| TWI707946B (en) | 2020-10-21 |
| CN107636524A (en) | 2018-01-26 |
| JPWO2017119406A1 (en) | 2018-10-25 |
| TW201736563A (en) | 2017-10-16 |
| WO2017119406A1 (en) | 2017-07-13 |
| JP6798978B2 (en) | 2020-12-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107636524B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| WO2014185374A1 (en) | Sealing agent for one drop fill process, vertically conducting material, and liquid crystal display element | |
| CN109196413B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN107250903B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| JP2016056361A (en) | Polymerizable compound, curable resin composition, sealing agent for liquid crystal display element, vertical conducting material, and liquid crystal display element | |
| JP6523167B2 (en) | Sealant for liquid crystal dropping method, vertical conduction material, and liquid crystal display element | |
| KR20160137944A (en) | Sealing agent for liquid crystal dropping methods, vertically conducting material and liquid crystal display element | |
| CN112840267A (en) | Sealing agent for display element, cured product, vertical conduction material, and display element | |
| WO2016186127A1 (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN108292067B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN107710061B (en) | Light-shielding sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| JP6126756B1 (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| TWI716440B (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| KR20190055015A (en) | A sealing agent for a liquid crystal display element, an upper and lower conductive material, and a liquid crystal display element | |
| CN109564371B (en) | Polymerizable compound, sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| JP6078698B1 (en) | Liquid crystal dropping method sealing agent, vertical conduction material, and liquid crystal display element | |
| CN107683435B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| JP6378970B2 (en) | Curable resin composition, liquid crystal display element sealing agent, vertical conduction material, and liquid crystal display element | |
| CN110168440B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN109196414B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| WO2017119260A1 (en) | Sealing agent for liquid crystal display elements, vertically conducting material and liquid crystal display element | |
| CN115996959A (en) | Thioxanthone compound, photopolymerization initiator, curable resin composition, composition for display element, sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN113874462A (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN111656270A (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| WO2018037861A1 (en) | Sealing agent for liquid crystal display elements, vertically conducting material, and liquid crystal display element |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |