CN110168442B - 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
- CN110168442B CN110168442B CN201880006654.1A CN201880006654A CN110168442B CN 110168442 B CN110168442 B CN 110168442B CN 201880006654 A CN201880006654 A CN 201880006654A CN 110168442 B CN110168442 B CN 110168442B
- Authority
- CN
- China
- Prior art keywords
- meth
- liquid crystal
- compound
- crystal display
- display element
- 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 108
- 239000000463 material Substances 0.000 title claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 title abstract description 12
- 238000007789 sealing Methods 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- -1 acrylic compound Chemical class 0.000 claims abstract description 77
- 239000000565 sealant Substances 0.000 claims abstract description 73
- 229920005989 resin Polymers 0.000 claims abstract description 28
- 239000011347 resin Substances 0.000 claims abstract description 28
- 239000003999 initiator Substances 0.000 claims abstract description 16
- 239000004593 Epoxy Substances 0.000 claims description 91
- 239000010419 fine particle Substances 0.000 claims description 13
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- 239000004020 conductor Substances 0.000 claims 1
- 230000007547 defect Effects 0.000 abstract description 11
- 239000011248 coating agent Substances 0.000 abstract description 7
- 238000000576 coating method Methods 0.000 abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 104
- 239000000758 substrate Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- 229920003986 novolac Polymers 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 15
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000012719 thermal polymerization Methods 0.000 description 8
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 7
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000011109 contamination Methods 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 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
- 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 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000013007 heat curing Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000006850 spacer group Chemical group 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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 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
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([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
- 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 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 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 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 238000007665 sagging 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
- 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
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-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
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-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
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-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
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-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
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- RJNVSQLNEALZLC-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]oxirane Chemical compound COC1=CC=CC=C1OCC1OC1 RJNVSQLNEALZLC-UHFFFAOYSA-N 0.000 description 1
- MVZODTFBTJNDMW-UHFFFAOYSA-N 2-[(2-methylphenyl)-[(2-methylphenyl)-(oxiran-2-yl)methoxy]methyl]oxirane Chemical compound CC1=CC=CC=C1C(C1OC1)OC(C=1C(=CC=CC=1)C)C1OC1 MVZODTFBTJNDMW-UHFFFAOYSA-N 0.000 description 1
- QWCOUYJXFUKDGD-UHFFFAOYSA-N 2-[(3-methylphenyl)-[(3-methylphenyl)-(oxiran-2-yl)methoxy]methyl]oxirane Chemical compound CC1=CC=CC(C(OC(C2OC2)C=2C=C(C)C=CC=2)C2OC2)=C1 QWCOUYJXFUKDGD-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-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
- VLKXLWGYPOUERV-UHFFFAOYSA-N 2-[3-(oxiran-2-ylmethoxy)propoxymethyl]oxirane Chemical compound C1OC1COCCCOCC1CO1 VLKXLWGYPOUERV-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-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
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-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
- 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 1
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 1
- FIEKVYPYFQSFTP-UHFFFAOYSA-N 6-methyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C FIEKVYPYFQSFTP-UHFFFAOYSA-N 0.000 description 1
- FYYIUODUDSPAJQ-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 2-methylprop-2-enoate Chemical compound C1C(COC(=O)C(=C)C)CCC2OC21 FYYIUODUDSPAJQ-UHFFFAOYSA-N 0.000 description 1
- FIWRUIQDDCPCOQ-UHFFFAOYSA-N C=CC(=O)OC1C=CC=C1 Chemical compound C=CC(=O)OC1C=CC=C1 FIWRUIQDDCPCOQ-UHFFFAOYSA-N 0.000 description 1
- PNVWNTUCFLZBSE-UHFFFAOYSA-N CC(O)COC(=O)c1ccccc1C(=O)OCCOC(=O)C=C Chemical compound CC(O)COC(=O)c1ccccc1C(=O)OCCOC(=O)C=C PNVWNTUCFLZBSE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-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
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-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
- FYYIUODUDSPAJQ-XVBQNVSMSA-N [(1S,6R)-7-oxabicyclo[4.1.0]heptan-3-yl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CC[C@H]2O[C@H]2C1 FYYIUODUDSPAJQ-XVBQNVSMSA-N 0.000 description 1
- LOCXTTRLSIDGPS-FVDSYPCUSA-N [(z)-[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(/CCCCCC)=N\OC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-FVDSYPCUSA-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
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 239000002518 antifoaming agent 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
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 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
- 230000001588 bifunctional effect Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- IADGHSROEWQWLL-UHFFFAOYSA-M butyl(trimethyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](C)(C)C IADGHSROEWQWLL-UHFFFAOYSA-M 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 230000006866 deterioration Effects 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
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 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
- 238000009826 distribution Methods 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
- 239000012847 fine chemical Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 230000007774 longterm Effects 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
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 150000002883 o-cresols Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003254 radicals Chemical class 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
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000002904 solvent 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
- 230000035882 stress 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
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229940007392 tylan Drugs 0.000 description 1
- WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
- 235000019375 tylosin Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Liquid Crystal (AREA)
- Sealing Material Composition (AREA)
- Polymerisation Methods In General (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
The purpose of the present invention is to provide a sealing agent for a liquid crystal display element, which has excellent coating properties and excellent curability with respect to light having a long wavelength, and which can suppress display defects when the liquid crystal display element is lit for a long period of time. Further, an 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. The present invention is a sealant for a liquid crystal display element, comprising a curable resin and a photopolymerization initiator, wherein the curable resin contains a (meth) acrylic compound having a molecular weight of 700 or more and 2000 or less, and the photopolymerization initiator contains a compound having a structure represented by the following formula (1). In the formula (1), the bonding position is represented by the formula.
Description
Technical Field
The present invention relates to a sealant for a liquid crystal display element, which has excellent coating properties and curability with respect to light having a long wavelength, and which can suppress display defects when the liquid crystal display element is lit up for a long period of time. The present invention also relates to a vertical conduction material and a liquid crystal display element, which are produced using the sealant for a liquid crystal display element.
Background
In recent years, as a method for manufacturing a liquid crystal display element such as a liquid crystal display unit, a liquid crystal dropping method called a dropping method using a photo-thermal curable sealing agent as disclosed in patent documents 1 and 2 has been used from the viewpoint of shortening the tact time and optimizing the amount of liquid crystal used.
In the one drop fill process, first, a frame-shaped seal pattern is formed on one of two transparent substrates with electrodes by dispensing. Next, 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 bonded, and the sealing portion is irradiated with light such as ultraviolet light to perform precuring. Thereafter, the liquid crystal is heated during annealing to perform main curing, thereby producing a liquid crystal display element. When the substrates are bonded under reduced pressure, the liquid crystal display element can be manufactured with extremely high efficiency, and this one drop fill process is currently the mainstream of a method for manufacturing a liquid crystal display element.
However, in the modern day in which various mobile devices with liquid crystal panels such as mobile phones and portable game machines are increasingly widespread, miniaturization of the devices is the most demanding issue. As a method for downsizing the device, narrowing of the frame of the liquid crystal display portion, for example, an operation of disposing the position of the sealing portion under the black matrix (hereinafter, also referred to as narrow frame design) is performed.
However, in the narrow-frame design, since the sealant is disposed directly below the black matrix, if the dropping process is performed, light irradiated when the sealant is photo-cured is blocked, and there is a problem that curing becomes insufficient without reaching the inside of the sealant. As described above, if the curing of the sealant becomes insufficient, an uncured sealant component is eluted into the liquid crystal, and a curing reaction due to the eluted sealant component progresses in the liquid crystal, thereby causing a problem of liquid crystal contamination.
In addition, generally, irradiation of ultraviolet rays is performed as a method of photocuring a sealant, but in a liquid crystal dropping process, since the sealant is cured after dropping a liquid crystal, there is a problem that the liquid crystal is deteriorated by irradiation of ultraviolet rays. In order to prevent deterioration of liquid crystal due to ultraviolet light, it is conceivable to blend a photopolymerization initiator having excellent reactivity with light having a long wavelength and to perform photocuring by using light having a long wavelength via a cut filter or the like. However, when only a photopolymerization initiator having excellent reactivity with light having a long wavelength is blended, it is not possible to sufficiently perform photocuring of a sealant using light having a long wavelength. Further, when a liquid crystal display element is lit for a long period of time after being manufactured, a sealant component which is slightly eluted into the liquid crystal before curing reacts to cause a display defect such as display unevenness.
Documents of the prior art
Patent literature
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 sealing agent for a liquid crystal display element, which has excellent coatability and curability against long-wavelength light and can suppress display defects when the liquid crystal display element is lit for a long period of time. Further, an 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, comprising a curable resin and a photopolymerization initiator, wherein the curable resin contains a (meth) acrylic compound having a molecular weight of 700 or more and 2000 or less, and the photopolymerization initiator contains a compound having a structure represented by the following formula (1).
[ solution 1]
In the formula (1), the bonding position is represented by the formula.
The present invention is described in detail below.
The inventors of the present invention found that: the present inventors have found that a (meth) acrylic compound having a molecular weight within a specific range and a photopolymerization initiator having a specific structure are used in combination to obtain a sealant for a liquid crystal display element which is excellent in coatability and curability against long-wavelength light and can suppress display defects when the liquid crystal display element is lit for a long period of time, 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 (meth) acrylic compound having a molecular weight of 700 to 2000. By using the (meth) acrylic compound having a molecular weight of 700 to 2000 in combination with a compound having a structure represented by the formula (1) described below, the obtained sealant for a liquid crystal display element is excellent in coatability and curability against long-wavelength light, and can suppress display defects when the liquid crystal display element is lit for a long period of time.
The molecular weight of the (meth) acrylic compound having a molecular weight of 700 to 2000 has a preferred lower limit of 750, a preferred upper limit of 1500, a more preferred lower limit of 800, and a more preferred upper limit of 1200.
In the present specification, the "molecular weight" is a molecular weight determined from a structural formula for a compound having a definite molecular structure, and may be expressed by a weight average molecular weight for a compound having a wide distribution of polymerization degrees and a compound having an indefinite modification site. In the present specification, the "weight average molecular weight" is a value measured by Gel Permeation Chromatography (GPC) and determined in terms of polystyrene. Examples of the column used for measuring the weight-average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko K.K.).
In the present specification, the "(meth) acrylic" refers to an acrylic or a methacrylic, the "(meth) acrylic compound" refers to a compound having a (meth) acryloyl group, and the "(meth) acryloyl group" refers to an acryloyl group or a methacryloyl group.
From the viewpoint of low liquid crystal contamination, the (meth) acrylic compound having a molecular weight of 700 or more and 2000 or less is preferably a phenol type (meth) acrylic compound, and more preferably a phenol type epoxy (meth) acrylate, in order to increase the viscosity gently and hardly deteriorate the coatability even when the molecular weight is increased to a high level.
In the present specification, the "(meth) acrylate" refers to an acrylate or a methacrylate. The "epoxy (meth) acrylate" refers to an epoxy (meth) acrylate in which all epoxy groups of an epoxy compound are reacted with (meth) acrylic acid to introduce a (meth) acryloyl group. That is, the "novolac epoxy (meth) acrylate" refers to a novolac epoxy (meth) acrylate in which all epoxy groups of a novolac epoxy compound are reacted with (meth) acrylic acid to introduce a (meth) acryloyl group.
Examples of the novolac-type epoxy (meth) acrylate include phenol novolac-type epoxy (meth) acrylate, o-cresol novolac-type epoxy (meth) acrylate, dicyclopentadiene novolac-type epoxy (meth) acrylate, biphenol novolac-type epoxy (meth) acrylate, and naphthol novolac-type epoxy (meth) acrylate. Among them, phenol novolac type epoxy (meth) acrylate is preferable.
The above-mentioned novolak type epoxy (meth) acrylate can be obtained by reacting all epoxy groups of a novolak type epoxy compound with (meth) acrylic acid in the presence of an alkaline catalyst according to a conventional method.
Examples of the novolac-type epoxy compound to be a raw material of the novolac-type epoxy (meth) acrylate include phenol novolac-type epoxy compounds, o-cresol novolac-type epoxy compounds, dicyclopentadiene novolac-type epoxy compounds, biphenol novolac-type epoxy compounds, naphthol novolac-type epoxy compounds, and the like. Among them, phenol novolac type epoxy compounds are preferable.
Further, as the above-mentioned phenol type (meth) acrylic compound, a partially (meth) acrylic acid-modified phenol type epoxy compound is also preferably used.
In the present specification, the "partially (meth) acrylic-modified novolac-type epoxy compound" refers to a substance in which a part of epoxy groups of the novolac-type epoxy compound reacts with (meth) acrylic acid to introduce a (meth) acryloyl group.
Examples of the partially (meth) acrylic-modified novolak-type epoxy compound include partially (meth) acrylic-modified novolak-type epoxy compounds, partially (meth) acrylic-modified o-cresol novolak-type epoxy compounds, partially (meth) acrylic-modified dicyclopentadiene novolak-type epoxy compounds, partially (meth) acrylic-modified diphenol novolak-type epoxy compounds, and partially (meth) acrylic-modified naphthol novolak-type epoxy compounds. Among them, a partially (meth) acrylic-modified phenol novolac-type epoxy compound is preferable.
The partial (meth) acrylic-modified novolak type epoxy compound can be obtained in a mixture of a partial (meth) acrylic-modified novolak type epoxy compound, a novolak type epoxy compound and a novolak type epoxy (meth) acrylate by reacting a part of epoxy groups of the novolak type epoxy compound with (meth) acrylic acid. Examples of the method for reacting a part of the epoxy groups of the above-mentioned phenolic epoxy compound with (meth) acrylic acid include a method of reacting the epoxy groups in the presence of a basic catalyst according to a conventional method.
Examples of the novolac-type epoxy compound to be a raw material of the partially (meth) acrylic-modified novolac-type epoxy compound include the same compounds as those of the novolac-type epoxy compound to be a raw material of the novolac-type epoxy (meth) acrylate.
Examples of the other compounds among the (meth) acrylic compounds having a molecular weight of 700 to 2000 include ethylene oxide-added bisphenol a epoxy (meth) acrylate, propylene oxide-added bisphenol a epoxy (meth) acrylate, and caprolactone-modified bisphenol a epoxy (meth) acrylate.
The curable resin may further contain another curable resin in addition to the (meth) acrylic compound having a molecular weight of 700 to 2000, within a range not impairing the object of the present invention.
When the curable resin contains the other curable resin, the content of the (meth) acrylic compound having a molecular weight of 700 or more and 2000 or less is preferably 2 parts by weight at the lower limit and 30 parts by weight at the upper limit in 100 parts by weight of the curable resin. By setting the content of the (meth) acrylic compound having a molecular weight of 700 or more and 2000 or less to 2 parts by weight or more, the obtained sealant for a liquid crystal display element is more excellent in the effect of suppressing display defects when the liquid crystal display element is lit for a long period of time. By setting the content of the (meth) acrylic compound having a molecular weight of 700 or more and 2000 or less to 30 parts by weight or less, the coating property of the obtained sealant for a liquid crystal display element becomes more excellent. The content of the (meth) acrylic compound having a molecular weight of 700 to 2000 is more preferably 3 parts by weight in the lower limit and 25 parts by weight in the upper limit.
As the other curable resin, a curable resin having a molecular weight of less than 700 is preferable. Examples of the curable resin having a molecular weight of less than 700 include a (meth) acrylic compound having a molecular weight of less than 700, an epoxy compound having a molecular weight of less than 700, and the like.
Examples of the (meth) acrylic compound having a molecular weight of less than 700 include a (meth) acrylate compound having a molecular weight of less than 700, an epoxy (meth) acrylate having a molecular weight of less than 700, and a urethane (meth) acrylate having a molecular weight of less than 700. Among them, epoxy (meth) acrylates having a molecular weight of less than 700 are preferable. From the viewpoint of high reactivity, the (meth) acrylic compound having a molecular weight of less than 700 is preferably a (meth) acrylic compound having 2 or more (meth) acryloyl groups in 1 molecule.
Examples of the monofunctional compound among the above (meth) acrylate compounds having a molecular weight of less than 700 include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-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, and mixtures thereof, Cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, phenoxydiethylene 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, bis (cyclopentadienyl) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2, 3, 3-tetrafluoropropyl (meth) acrylate, 1H, 5H-octafluoropentyl (meth) acrylate, imide (meth) acrylate, dimethylaminoethyl (meth) acrylate, bis (meth) acrylate, and (meth) acrylate, bis (meth) acrylate, and (meth) acrylate, Diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethylsuccinic acid, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxyethyl 2-hydroxypropyl phthalate, 2- (meth) acryloyloxyethyl phosphate, glycidyl (meth) acrylate, and the like.
Examples of the bifunctional compound among the (meth) acrylate compounds having a molecular weight of less than 700 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, 2-n-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and mixtures thereof, Dimethylol dicyclopentadienyl di (meth) acrylate, ethylene oxide-modified isocyanuric acid di (meth) acrylate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, carbonate diol di (meth) acrylate, and the like.
Examples of the trifunctional or higher compound in the (meth) acrylate compound having a molecular weight of less than 700 include trimethylolpropane tri (meth) acrylate, glycerol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tri (meth) acryloyloxyethyl phosphate, pentaerythritol tetra (meth) acrylate, bis (trimethylolpropane) tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.
Examples of the epoxy (meth) acrylate having a molecular weight of less than 700 include compounds 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 epoxy (meth) acrylate having a molecular weight of less than 700 include bisphenol a diglycidyl ether, bisphenol F diglycidyl ether, bisphenol E diglycidyl ether, hydrogenated bisphenol a diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol E diglycidyl ether, resorcinol diglycidyl ether, biphenyl-4, 4' -diylbis (glycidyl ether), 1, 6-naphthalenediylbis (glycidyl ether), ethylene glycol diglycidyl ether, 1, 3-propanediol diglycidyl ether, and 1, 4-butanediol diglycidyl ether.
The urethane (meth) acrylate having a molecular weight of less than 700 can be obtained, for example, by reacting a (meth) acrylic acid derivative having a hydroxyl group with an isocyanate compound in the presence of a catalytic amount of a tin-based compound.
Examples of the isocyanate compound include isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4, 4' -diisocyanate (MDI), hydrogenated MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, Xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, and tetramethylxylylene diisocyanate.
Examples of the (meth) acrylic acid derivative having a hydroxyl group include hydroxyalkyl (meth) acrylates and mono (meth) acrylates of glycols.
Examples of the hydroxyalkyl (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
Examples of the dihydric alcohol include ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 3-butanediol, and 1, 4-butanediol.
Further, as the above-mentioned (meth) acrylic compound having a molecular weight of less than 700, a partially (meth) acrylic acid-modified epoxy compound having a molecular weight of less than 700 may be used.
In the present specification, the term "part of the (meth) acrylic acid-modified epoxy compound" means: a compound in which a part of epoxy groups of an epoxy compound reacts with (meth) acrylic acid to introduce a (meth) acryloyl group.
Examples of the epoxy compound to be a raw material for synthesizing the partially (meth) acrylic acid-modified epoxy compound having a molecular weight of less than 700 include epoxy compounds to be a raw material for synthesizing the epoxy (meth) acrylate having a molecular weight of less than 700.
Examples of the epoxy compound having a molecular weight of less than 700 include epoxy compounds which are raw materials for synthesizing the epoxy (meth) acrylate having a molecular weight of less than 700.
The sealant for a liquid crystal display element of the present invention contains a photopolymerization initiator.
The photopolymerization initiator contains a compound having a structure represented by the formula (1). The compound having the structure represented by the formula (1) is excellent in reactivity to long-wavelength light and can suppress display defects when the liquid crystal display element is lit for a long period of time by using the compound in combination with the (meth) acrylic compound having the molecular weight of 700 or more and 2000 or less.
The compound having the structure represented by the above formula (1) may be a compound having 1 molecule of the structure represented by the above formula (1). The compound having 1 structure represented by the formula (1) in the molecule of 1 is preferably a compound represented by the following formula (2-1) and/or a compound represented by the following formula (2-2).
[ solution 2]
In the formulas (2-1) and (2-2), R is a structure derived from a monofunctional epoxy compound.
Examples of the method for producing the compound represented by the formula (2-1) include a method in which 2- (carboxymethoxy) -9H-thioxanth-9-one and a monofunctional epoxy compound are reacted with each other in the presence of a basic catalyst under stirring at 80 ℃ to 130 ℃ for 6 to 72 hours.
Further, as a method for producing the compound represented by the above formula (2-2), for example, a method of reacting 2-hydroxy-9H-thioxanth-9-one with a monofunctional epoxy compound in the presence of a basic catalyst under conditions of 80 ℃ to 130 ℃ with stirring for 6 to 72 hours, and the like can be mentioned.
Hereinafter, the 2- (carboxymethoxy) -9H-thioxanthon-9-one and the 2-hydroxy-9H-thioxanthon-9-one are also referred to as "starting thioxanthone derivatives".
The above monofunctional epoxy compound preferably has: an aromatic ring having at least 1 or more substituents having 1 or more carbon atoms or an aliphatic ring having at least 1 or more substituents having 1 or more carbon atoms.
Examples of the aromatic ring or the aliphatic ring include aromatic rings such as benzene ring, naphthalene ring, anthracene ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cyclooctane ring, norbornene ring, tricyclodecane ring, and rings in which at least 1 or more hydrogen atoms in the aliphatic ring are substituted with a substituent having 1 or more carbon atoms.
The substituent having 1 or more carbon atoms may be linear or branched. When the substituent having 1 or more carbon atoms is linear, the number of carbon atoms is preferably 6 or more, and more preferably 10 or more. When the substituent having 1 or more carbon atoms is branched, it is preferable that the carbon number is 4 or more. The number of carbons of the substituent having 1 or more carbon atoms in the aromatic ring or the aliphatic ring is preferably a number such that the molecular weight of the monofunctional epoxy compound becomes 300 or less, which will be described later.
The substituent having 1 or more carbon atoms in the aromatic ring or the aliphatic ring is preferably an alkyl group.
Examples of the monofunctional epoxy compound include alkylphenyl glycidyl ether, tosylate having a glycidyl group, 2-epoxy-4-vinylcyclohexane, and 3, 4-epoxycyclohexylmethyl methacrylate.
Examples of the alkylphenyl glycidyl ether include o-methylphenylglycidyl ether, m-methylphenylglycidyl ether, p-methylphenylglycidyl ether, and p-tert-butylphenyl glycidyl ether.
Examples of commercially available products among the above monofunctional epoxy compounds include a monofunctional epoxy compound manufactured by Nagase ChemteX, a monofunctional epoxy compound manufactured by ADEKA, a monofunctional epoxy compound manufactured by Mitsubishi chemical company, a monofunctional epoxy compound manufactured by Tokyo chemical company, and a monofunctional epoxy compound manufactured by Dailuo company.
Examples of the monofunctional epoxy compound manufactured by Nagase ChemteX include Denacol EX-146.
Examples of the monofunctional epoxy compound manufactured by the ADEKA company include ED-509S, ED-509E, ED-529.
Examples of the monofunctional epoxy compound manufactured by Mitsubishi chemical corporation include YED-122.
Examples of the monofunctional epoxy compound manufactured by Tokyo chemical industry Co., Ltd include glycidyl 2-methoxyphenyl ether and 1-methyl-1, 2-epoxycyclohexane.
Examples of the monofunctional epoxy compound manufactured by the above-mentioned Daiiluo corporation include CELLOXIDE 2000 and CYCLOMER M100.
The monofunctional epoxy compound preferably has a molecular weight of 300 or less from the viewpoint of compatibility between the compound having a structure represented by the formula (1) and the curable resin.
The ratio of the starting thioxanthone derivative to the monofunctional epoxy compound is preferably 1: 1 to 10: 1 in terms of a molar ratio, when the starting thioxanthone derivative is reacted with the monofunctional epoxy compound. When the ratio of the thioxanthone derivative as the raw material to the monofunctional epoxy compound is within this range, the compound represented by the formula (2-1) or the compound represented by the formula (2-2) can be produced in high yield.
The basic catalyst used for the reaction of the starting thioxanthone derivative with the monofunctional epoxy compound is preferably a 3-valent organic phosphoric acid compound and/or an amine compound.
Specific examples of the basic catalyst include triphenylphosphine, triethylamine, tripropylamine, tetramethylethylenediamine, dimethyllaurylamine, triethylbenzylammonium chloride, trimethylcetylammonium bromide, tetrabutylammonium bromide, trimethylbutylphosphonium bromide, tetrabutylphosphonium bromide, and the like. Among them, triphenylphosphine is preferable.
The basic catalyst may be supported on a polymer and used in the form of a polymer-supported basic catalyst.
The compound having the structure represented by the above formula (1) may be a compound having 2 or more structures represented by the above formula (1) in 1 molecule. The compound having 2 or more structures represented by the above formula (1) in the above 1 molecule is preferably a compound represented by the following formula (3).
[ solution 3]
In the formula (3), n is 1 to 10 (average value).
Examples of commercially available products among the compounds represented by the above formula (3) include Omnipol TX (manufactured by IGM Resins).
The lower limit of the content of the compound having the structure represented by formula (1) is preferably 0.5 part by weight, and the upper limit is preferably 20 parts by weight, based on 100 parts by weight of the curable resin. By setting the content of the compound having the structure represented by the formula (1) to 0.5 parts by weight or more, the obtained sealant for a liquid crystal display element is more excellent in curability against long-wavelength light. By setting the content of the compound having the structure represented by the above formula (1) to 20 parts by weight or less, the effect of the obtained sealant for a liquid crystal display element of suppressing display defects of the liquid crystal display element becomes more excellent. The lower limit of the content of the compound having the structure represented by the above formula (1) is more preferably 2 parts by weight, and the upper limit is more preferably 10 parts by weight.
The photopolymerization initiator may contain other photopolymerization initiators than the compound having the structure represented by the formula (1) in a range not impairing the object of the present invention.
Examples of the other photopolymerization initiator include bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide, 1- (4- (phenylthio) phenyl) -1, 2-octanedione 2- (O-benzoyloxime), and O-acetyl-1- (6- (2-methylbenzoyl) -9-ethyl-9H-carbazol-3-yl) ethanone oxime.
The sealant for liquid crystal display elements of the present invention may contain a thermal polymerization initiator within a range not impairing the object of the present invention.
Examples of the thermal polymerization initiator include thermal polymerization initiators containing azo compounds, organic peroxides, and the like. Among them, a polymeric azo initiator containing a polymeric azo compound is preferable.
The thermal polymerization initiators may be used alone or in combination of 2 or more.
In the present specification, the "macromolecular azo compound" means: a compound having an azo group, which generates a radical capable of curing a (meth) acryloyloxy group by heat, and which has a number average molecular weight of 300 or more.
The number average molecular weight of the macromolecular azo compound has a preferred lower limit of 1000 and a preferred upper limit of 30 ten thousand. When the number average molecular weight of the macromolecular azo compound is in this range, the azo compound can be easily mixed with the curable resin while suppressing liquid crystal contamination. The number average molecular weight of the macromolecular azo compound is preferably lower than 5000, more preferably upper than 10 ten thousand, even more preferably lower than 1 ten thousand, and even more preferably upper than 9 ten thousand.
In the present specification, the number average molecular weight is a value determined by measuring with Gel Permeation Chromatography (GPC) using tetrahydrofuran as a solvent and converting into polystyrene. 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 macromolecular azo compound include compounds having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via an azo group.
The polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via an azo group is preferably a compound having a polyethylene oxide structure.
Specific examples of the polymer azo compound 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.
Examples of commercially available products among the above-mentioned macromolecular azo compounds include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (all manufactured by Fuji film & Wako pure chemical industries, Ltd.).
Examples of the non-polymeric azo compound include V-65 and V-501 (both manufactured by Fuji photo film and Wako pure chemical industries, Ltd.).
Examples of the organic peroxide include ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
The lower limit of the content of the thermal polymerization initiator is preferably 0.05 parts by weight, and the upper limit is preferably 10 parts by weight, based on 100 parts by weight of the curable resin. By setting the content of the thermal polymerization initiator to 0.05 parts by weight or more, the sealant for a liquid crystal display element of the present invention is more excellent in thermosetting property. By setting the content of the thermal polymerization initiator to 10 parts by weight or less, the sealant for a liquid crystal display element of the present invention is more excellent in low liquid crystal contamination and storage stability. The lower limit of the content of the thermal polymerization initiator is more preferably 0.1 part by weight, and the upper limit is more preferably 5 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a thermosetting agent.
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 suitably used.
The thermosetting agent may be used alone, or 2 or more of them may be used in combination.
Examples of the organic acid hydrazide include sebacic dihydrazide, isophthalic dihydrazide, adipic dihydrazide, malonic dihydrazide, and the like.
Examples of commercially available products among the above-mentioned organic acid hydrazides include organic acid hydrazides manufactured by Otsuka chemical company, organic acid hydrazides manufactured by Aomoto Fine chemical company, and the like.
Examples of the organic acid hydrazide available from Otsuka chemical company include SDH and ADH.
Examples of the organic acid hydrazide manufactured by Aomoto Chemicals include AMICURE VDH, AMICURE VDH-J, AMICURE UDH and AMICURE UDH-J.
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. When the content of the thermosetting agent is in this range, the thermosetting property can be further improved without deteriorating the coating property of the obtained sealant for a liquid crystal display element. The more preferable upper limit of the content of the thermal curing 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, and the like.
As the filler, an inorganic filler or an organic filler can be used.
Examples of the inorganic filler include 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.
Examples of the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles.
The fillers may be used alone, or 2 or more of them may be used in combination.
The lower limit of the content of the filler in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is preferably 10 parts by weight, and the upper limit is preferably 70 parts by weight. When the content of the filler is in this range, the effect of improving adhesiveness and the like becomes more excellent without deteriorating coatability and the like. The lower limit of the content of the filler is more preferably 20 parts by weight, and the upper limit is more preferably 60 parts 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.
As the silane coupling agent, for example, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane and the like are suitably used. These compounds have an excellent effect of improving adhesion to a substrate or the like, and can inhibit the outflow of a curable resin into a liquid crystal by chemically bonding with the curable resin.
The content of the silane coupling agent in 100 parts by weight of the sealant for a liquid crystal display element of the present invention has a preferable lower limit of 0.1 part by weight and a preferable upper limit of 10 parts by weight. When the content of the silane coupling agent is in this range, the effect of suppressing the occurrence of liquid crystal contamination and improving the adhesion is further enhanced. The lower limit of the content of the silane coupling agent is more preferably 0.3 parts by weight, and the upper limit is more preferably 5 parts by weight.
The sealant for a liquid crystal display element of the present invention may further contain additives such as a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, and a polymerization inhibitor, 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 a curable resin, a photopolymerization initiator, and a silane coupling agent added as needed, using a mixer such as a homogenizer, a homomixer, a universal mixer, a planetary mixer, a kneader, or a triple roll mill.
The conductive fine particles are mixed in the sealant for a liquid crystal display element of the present invention, whereby a vertical conduction material can be produced. Such a vertical conduction material containing the sealant for a 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 conductive connection can be performed without damaging the transparent substrate or the like due to the excellent elasticity of the resin fine particles.
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 method is preferably used, and specifically, a method including the following steps, for example, is exemplified.
A liquid crystal display element can be obtained by a method including the steps of, first: a step of forming a frame-shaped seal pattern by applying the sealant for a liquid crystal display element of the present invention to one of two substrates such as a glass substrate with an electrode such as an ITO film and a polyethylene terephthalate substrate by screen printing, dispenser coating, or the like; next, the following steps are performed: a step of applying a liquid crystal droplet in a state where the sealant for a liquid crystal display element of the present invention is not cured to a frame of a seal pattern of a substrate, and stacking another substrate under vacuum; thereafter, the following steps are performed: and a step of irradiating the seal pattern portion of the sealant for a liquid crystal display element of the present invention with light through a 400nm cut-off filter or the like to thereby photocure the sealant with light of a long wavelength. In addition, the step of heat-curing the sealant may be performed in addition to the step of photocuring the sealant.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention can provide a sealant for a liquid crystal display element, which has excellent coatability and curability against long-wavelength light and can suppress display defects when the liquid crystal display element is lit for a long period of time. 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 below with reference to examples, but the present invention is not limited to these examples.
(preparation of phenol-formaldehyde type epoxy acrylate B)
557 parts by weight of a phenol novolac epoxy compound (product of DIC Co., Ltd. "EPICLON-740") was dissolved in 1800mL of toluene, and 0.5 part by weight of triphenylphosphine was added thereto to prepare a uniform solution. 244 parts by weight of acrylic acid was added dropwise to the resulting solution over 2 hours under reflux stirring, followed by reflux stirring for a further 6 hours. Subsequently, the toluene was removed under reduced pressure to obtain a novolac-type epoxy acrylate B.
The structure of the obtained novolak type epoxy acrylate B was determined by1H-NMR、13C-NMR and FT-IR were confirmed.
Further, the weight average molecular weight of the obtained novolak type epoxy acrylate B was 1400.
(preparation of phenol type epoxy acrylate C)
965 parts by weight of a phenol novolac type epoxy compound (available from DIC corporation, "EPICLON N-770") were dissolved in 2500mL of toluene, and 0.5 part by weight of triphenylphosphine was added thereto to prepare a uniform solution. 432 parts by weight of acrylic acid was added dropwise to the resulting solution over 2 hours under reflux stirring, followed by further reflux stirring for 6 hours. Subsequently, the toluene was removed under reduced pressure to obtain a novolak type epoxy acrylate C.
The structure of the obtained novolak type epoxy acrylate C was determined by1H-NMR、13C-NMR and FT-IR were confirmed.
Further, the weight average molecular weight of the obtained novolak type epoxy acrylate C was 2700.
(preparation of Compound represented by the formula (2-1))
The compound represented by the above formula (2-1) was obtained by reacting 87 parts by weight of 2- (carboxymethoxy) -9H-thioxanth-9-one with 62 parts by weight of p-tert-butylphenyl glycidyl ether (manufactured by ADEKA, "ED-509S") as a monofunctional epoxy compound in the presence of a basic catalyst while stirring at 110 ℃ for 48 hours. As the basic catalyst, PS-PPh was used3(basic catalyst obtained by supporting triphenylphosphine on Polystyrene (PS) manufactured by BIOTAGE JAPAN) 5.2 parts by weight.
The compound represented by the above formula (2-1) is obtained by1H-NMR、13C-NMR and FT-IR were confirmed.
In addition, the mixing ratio of 2- (carboxymethoxy) -9H-thioxanth-9-one to p-tert-butylphenyl glycidyl ether was 1: 1 in terms of molar ratio, based on 2- (carboxymethoxy) -9H-thioxanth-9-one to p-tert-butylphenyl glycidyl ether.
(preparation of Compound represented by formula (2-2))
The compound represented by the above formula (2-2) was obtained by reacting 69 parts by weight of 2-hydroxy-9H-thioxanth-9-one with 62 parts by weight of p-tert-butylphenyl glycidyl ether (manufactured by ADEKA, "ED-509S") as a monofunctional epoxy compound in the presence of a basic catalyst while stirring at 110 ℃ for 48 hours. As the basic catalyst, PS-PPh was used 3(manufactured by BIOTAGE JAPAN Ltd.)Basic catalyst obtained by supporting triphenylphosphine on Polystyrene (PS) 5.2 parts by weight.
The compound represented by the above formula (2-2) is obtained by1H-NMR、13C-NMR and FT-IR were confirmed.
In addition, the mixing ratio of 2-hydroxy-9H-thioxanth-9-one to p-tert-butylphenyl glycidyl ether was 1: 1 in terms of molar ratio, 2-hydroxy-9H-thioxanth-9-one to p-tert-butylphenyl glycidyl ether.
(examples 1 to 9 and comparative examples 1 to 4)
The respective materials were mixed with a planetary mixer (manufactured by THINKY, "あおとり tylan") at the mixing ratios described in tables 1 and 2, and then mixed with a three-roll mill to prepare sealants for liquid crystal display elements of examples 1 to 9 and comparative examples 1 to 4.
< evaluation >
The following evaluations were made with respect to the sealants for liquid crystal display elements obtained in examples and comparative examples. The results are shown in tables 1 and 2.
(coatability)
The sealant for liquid crystal display elements obtained in examples and comparative examples was applied to a glass substrate using a dispenser (manufactured by Musashi Engineering, "SHOTMASTER 300") with a dispensing nozzle fixed at 400 μm, a nozzle gap fixed at 30 μm, and a discharge pressure fixed at 300 kPa. The coatability was evaluated by marking "o" as a sealant that could be coated without blush or sagging, marking "Δ" as a sealant that slightly blush or sagging, and marking "x" as a sealant that had large coating breaks or coating irregularities, or that could not be coated at all.
(photo-curing)
1 part by weight of spacer particles (Micropearl SI-H050, manufactured by waterlogging chemical industries, Ltd.) was dispersed in 100 parts by weight of each of the sealants for liquid crystal display elements obtained in examples and comparative examples. Next, the sealant was filled into a syringe for dispensing (manufactured by Musashi Engineering, Inc.; "PSY-10E"), defoamed, and then dispensed by a dispenser (Musashi Engineering)"SHOTMASTER 300", manufactured by aging corporation) on a glass substrate. The same size glass substrate was bonded to the substrate under a reduced pressure of 5Pa by a vacuum bonding apparatus. The sealant portion of the attached glass substrate was irradiated with 100mW/cm using a metal halide lamp2For 10 seconds. The light irradiation was performed in two forms, a case without a 400nm cut filter and a case with a 400nm cut filter.
The sealant was subjected to FT-IR measurement using an infrared spectrometer (manufactured by BIORAD, "FTS 3000"), and the amount of change in the peak derived from the (meth) acryloyl group before and after light irradiation was measured, thereby evaluating the curability. The photocurability was evaluated by designating the case where the peak derived from a (meth) acryloyl group after light irradiation was reduced by 95% or more as "very good", the case where the peak derived from a (meth) acryloyl group after light irradiation was reduced by 85% or more and less than 95% as "o", the case where the peak derived from a (meth) acryloyl group after light irradiation was reduced by 75% or more and less than 85% as "Δ", and the case where the peak derived from a (meth) acryloyl group after light irradiation was reduced by 75% or less as "x".
(display Performance of liquid Crystal display element in Long-term Lighting)
1 part by weight of spacer particles (Micropearl SI-H050, manufactured by waterlogging chemical industries, Ltd.) was dispersed in 100 parts by weight of each of the sealants for liquid crystal display elements obtained in examples and comparative examples. Next, the sealant was filled in a syringe for dispensing (manufactured by Musashi Engineering, "PSY-10E") and subjected to defoaming treatment, and then the sealant was coated in a frame shape on one of 2 transparent electrode substrates with an ITO film by a dispenser (manufactured by Musashi Engineering, "SHOTMASTER 300"). Subsequently, minute droplets of TN liquid crystal (JC-5001 LA, manufactured by CHISSO Co., Ltd.) were applied dropwise into the frame of the sealant by a liquid crystal dropping apparatus, and the other transparent electrode substrate was bonded under a reduced pressure of 5Pa by a vacuum bonding apparatus. The sealant portion of the transparent electrode substrate was irradiated with 100mW/cm using a metal halide lamp through a 400nm cut-off filter2After 10 seconds, the sealant was cured by heating at 120 ℃ for 1 hour to obtain a liquid crystal display element.
The obtained liquid crystal display element was continuously lit using a white LED lamp while applying a voltage for 100 hours in an environment of 85 ℃ and 85% RH, and the degree of display unevenness was visually confirmed.
The display performance of the liquid crystal display element was evaluated by regarding a case where no display unevenness was observed in the liquid crystal display element as "excellent", a case where slight display unevenness was observed in the peripheral portion as "o", a case where significant severe display unevenness was observed in the peripheral portion as "Δ", and a case where significant severe display unevenness was observed not only in the peripheral portion but also in the central portion as "x".
Note that the liquid crystal display elements evaluated as "cyron" and "∘" are levels that have no problem at all in practical use, "Δ" is a level that may cause a problem depending on the display design of the liquid crystal display element, and "×" is a level that is not practical.
[ Table 1]
[ Table 2]
Industrial applicability
The present invention can provide a sealant for a liquid crystal display element, which has excellent coatability and curability with respect to light having a long wavelength, and can suppress display defects when the liquid crystal display element is lit for a long period of time. 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 (7)
1. A sealant for a liquid crystal display element, comprising a curable resin and a photopolymerization initiator,
The curable resin contains a (meth) acrylic compound having a molecular weight of 700 to 2000,
the (meth) acrylic compound having a molecular weight of 700 to 2000 is a phenol-formaldehyde type (meth) acrylic compound,
the photopolymerization initiator comprises a compound having a structure represented by the following formula (1),
in the formula (1), the symbol represents a bonding site.
2. The sealant for a liquid crystal display element according to claim 1, wherein the compound having the structure represented by the formula (1) is a compound having 1 structure represented by the formula (1) in 1 molecule.
3. The sealant for a liquid crystal display element according to claim 2, wherein the compound having the structure represented by the formula (1) is a compound represented by the following formula (2-1) and/or a compound represented by the following formula (2-2),
in the formulas (2-1) and (2-2), R is a structure derived from a monofunctional epoxy compound.
4. The sealant for a liquid crystal display element according to claim 1, wherein the compound having the structure represented by the formula (1) is a compound having 2 or more structures represented by the formula (1) in 1 molecule.
5. The sealant for a liquid crystal display element according to claim 4, wherein the compound having the structure represented by the formula (1) is a compound represented by the following formula (3),
In the formula (3), n is 1 to 10 in average value.
6. A vertical conduction material comprising the sealant for liquid crystal display element according to claim 1, 2, 3, 4 or 5 and conductive fine particles.
7. A liquid crystal display element produced by using the sealant for a liquid crystal display element according to claim 1, 2, 3, 4 or 5 or the vertically conducting material according to claim 6.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2017138033 | 2017-07-14 | ||
| JP2017-138033 | 2017-07-14 | ||
| PCT/JP2018/025334 WO2019013065A1 (en) | 2017-07-14 | 2018-07-04 | Sealing agent for liquid crystal display elements, vertical conduction material, and liquid crystal display element |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110168442A CN110168442A (en) | 2019-08-23 |
| CN110168442B true CN110168442B (en) | 2022-06-28 |
Family
ID=65001318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880006654.1A Active CN110168442B (en) | 2017-07-14 | 2018-07-04 | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP7184647B2 (en) |
| KR (1) | KR102578300B1 (en) |
| CN (1) | CN110168442B (en) |
| TW (1) | TWI780174B (en) |
| WO (1) | WO2019013065A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113651904B (en) * | 2021-08-12 | 2023-05-12 | 管和平 | Photopolymerizable single-component thioxanthone photoinitiator |
Family Cites Families (13)
| 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 |
| JP5433438B2 (en) * | 2010-01-22 | 2014-03-05 | 日本化薬株式会社 | Liquid crystal sealing agent for thermosetting liquid crystal dropping method and liquid crystal display cell using the same |
| WO2014192880A1 (en) * | 2013-05-31 | 2014-12-04 | 積水化学工業株式会社 | Sealing agent for display elements |
| JP5632978B1 (en) * | 2013-06-28 | 2014-11-26 | 太陽インキ製造株式会社 | Photocurable composition and cured product thereof |
| CN105579898B (en) * | 2013-11-13 | 2017-07-21 | 积水化学工业株式会社 | Sealing material for liquid crystal display device, up and down conductive material and liquid crystal display cells |
| WO2015083663A1 (en) * | 2013-12-05 | 2015-06-11 | 積水化学工業株式会社 | Polymerizable monomer, polymer compound, photocurable resin composition, sealing element for liquid crystal display element, vertical conduction material, and liquid crystal display element |
| JP6216260B2 (en) * | 2014-02-12 | 2017-10-18 | 積水化学工業株式会社 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
| JP6454217B2 (en) * | 2014-05-13 | 2019-01-16 | 積水化学工業株式会社 | Modified dialkylaminobenzoic acid-based compound, modified thioxanthone derivative, photocurable resin composition, liquid crystal display element sealing agent, vertical conduction material, and liquid crystal display element |
| JP6046866B1 (en) * | 2015-05-08 | 2016-12-21 | 積水化学工業株式会社 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
| KR102588717B1 (en) * | 2015-06-02 | 2023-10-12 | 세키스이가가쿠 고교가부시키가이샤 | Sealing agent for liquid crystal display elements, vertically conducting material and liquid crystal display element |
| JP6197020B2 (en) * | 2015-12-17 | 2017-09-13 | 三井化学株式会社 | Photocurable resin composition, display element sealant, liquid crystal sealant, liquid crystal display panel, and method for producing the same |
| JP2017149794A (en) * | 2016-02-22 | 2017-08-31 | 三井化学株式会社 | Photocurable resin composition, display element sealant, liquid crystal sealant and liquid crystal display panel |
-
2018
- 2018-07-04 CN CN201880006654.1A patent/CN110168442B/en active Active
- 2018-07-04 JP JP2018540880A patent/JP7184647B2/en active Active
- 2018-07-04 WO PCT/JP2018/025334 patent/WO2019013065A1/en active Application Filing
- 2018-07-04 KR KR1020197015735A patent/KR102578300B1/en active IP Right Grant
- 2018-07-06 TW TW107123506A patent/TWI780174B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| KR102578300B1 (en) | 2023-09-13 |
| JP7184647B2 (en) | 2022-12-06 |
| WO2019013065A1 (en) | 2019-01-17 |
| JPWO2019013065A1 (en) | 2020-05-07 |
| KR20200032026A (en) | 2020-03-25 |
| TWI780174B (en) | 2022-10-11 |
| TW201908452A (en) | 2019-03-01 |
| CN110168442A (en) | 2019-08-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110168441B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN111372952B (en) | Photopolymerization initiator, sealing agent for display element, vertical conduction material, display element, and compound | |
| WO2017119406A1 (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| JP6539160B2 (en) | Sealant for liquid crystal display element and vertical conduction material | |
| JP6523167B2 (en) | Sealant for liquid crystal dropping method, vertical conduction material, and liquid crystal display element | |
| CN110168442B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN111771160A (en) | Sealing agent for liquid crystal element, vertical conduction material, and liquid crystal element | |
| TW202028409A (en) | Sealant for display element, cured product, vertical conductive material, and display element | |
| CN107710060B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| JPWO2018062166A1 (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| TWI813690B (en) | Sealant for liquid crystal display element, upper and lower conduction material, and liquid crystal display element | |
| TWI747862B (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| CN110325904B (en) | Sealing agent for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| WO2019013194A1 (en) | Sealing agent for liquid crystal display elements, vertically conducting material and liquid crystal display element | |
| JP7029027B1 (en) | Sealant for display element, vertical conduction material, and display element | |
| JPWO2018062168A1 (en) | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| TWI731173B (en) | Sealant 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 | |
| TW202104517A (en) | Curable resin composition, sealing agent for liquid crystal display element, vertical conductive material, and liquid crystal display element | |
| JP2020042089A (en) | Liquid crystal display element sealant, vertical conductive material, and liquid crystal display element | |
| WO2017183583A1 (en) | Sealant for liquid crystal display element, method for manufacturing sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element | |
| JP2017132863A (en) | Oxime ester initiator, curable resin composition, sealant for liquid crystal display elements, vertical conduction 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 |