TWI714709B - Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element - Google Patents
Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element Download PDFInfo
- Publication number
- TWI714709B TWI714709B TW106101770A TW106101770A TWI714709B TW I714709 B TWI714709 B TW I714709B TW 106101770 A TW106101770 A TW 106101770A TW 106101770 A TW106101770 A TW 106101770A TW I714709 B TWI714709 B TW I714709B
- Authority
- TW
- Taiwan
- Prior art keywords
- liquid crystal
- compound
- crystal display
- meth
- acrylate
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 114
- 239000000565 sealant Substances 0.000 title claims abstract description 34
- 239000000463 material Substances 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 142
- 238000007789 sealing Methods 0.000 claims abstract description 52
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 32
- 229920005989 resin Polymers 0.000 claims abstract description 29
- 239000011347 resin Substances 0.000 claims abstract description 29
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 9
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000004020 conductor Substances 0.000 claims 1
- 238000011109 contamination Methods 0.000 abstract description 20
- 239000003999 initiator Substances 0.000 abstract description 14
- 238000010526 radical polymerization reaction Methods 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 67
- -1 acrylic compound Chemical class 0.000 description 38
- 239000003822 epoxy resin Substances 0.000 description 23
- 229920000647 polyepoxide Polymers 0.000 description 23
- 239000000758 substrate Substances 0.000 description 21
- 239000004593 Epoxy Substances 0.000 description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 8
- 239000010936 titanium Substances 0.000 description 8
- 229910052719 titanium Inorganic materials 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 7
- 239000010419 fine particle Substances 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- 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 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000000475 sunscreen effect Effects 0.000 description 4
- 239000000516 sunscreening agent Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 125000005577 anthracene group Chemical group 0.000 description 3
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 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 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 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
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 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
- 239000006229 carbon black Substances 0.000 description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000009413 insulation Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 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
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 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
- VLTYTTRXESKBKI-UHFFFAOYSA-N (2,4-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VLTYTTRXESKBKI-UHFFFAOYSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- NDWVRLFFXDNHQF-UHFFFAOYSA-N 1-ethyl-2-prop-2-enoyloxycyclohexane-1,2-dicarboxylic acid Chemical compound CCC1(C(O)=O)CCCCC1(OC(=O)C=C)C(O)=O NDWVRLFFXDNHQF-UHFFFAOYSA-N 0.000 description 1
- TURGQPDWYFJEDY-UHFFFAOYSA-N 1-hydroperoxypropane Chemical compound CCCOO TURGQPDWYFJEDY-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- MODNLDNPMHIXHC-UHFFFAOYSA-N 2-(2-hydroxyethoxy)anthracene-9,10-dione Chemical compound OCCOC1=CC=2C(C3=CC=CC=C3C(C=2C=C1)=O)=O MODNLDNPMHIXHC-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- YKVRVKRHNARYLS-UHFFFAOYSA-N 3-(2-hydroxypropyl)phthalic acid Chemical compound OC(CC1=C(C(C(=O)O)=CC=C1)C(=O)O)C YKVRVKRHNARYLS-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
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- XRUKRHLZDVJJSX-UHFFFAOYSA-N 4-cyanopentanoic acid Chemical compound N#CC(C)CCC(O)=O XRUKRHLZDVJJSX-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
- KSMGAOMUPSQGTB-UHFFFAOYSA-N 9,10-dibutoxyanthracene Chemical compound C1=CC=C2C(OCCCC)=C(C=CC=C3)C3=C(OCCCC)C2=C1 KSMGAOMUPSQGTB-UHFFFAOYSA-N 0.000 description 1
- GJNKQJAJXSUJBO-UHFFFAOYSA-N 9,10-diethoxyanthracene Chemical compound C1=CC=C2C(OCC)=C(C=CC=C3)C3=C(OCC)C2=C1 GJNKQJAJXSUJBO-UHFFFAOYSA-N 0.000 description 1
- LBQJFQVDEJMUTF-UHFFFAOYSA-N 9,10-dipropoxyanthracene Chemical compound C1=CC=C2C(OCCC)=C(C=CC=C3)C3=C(OCCC)C2=C1 LBQJFQVDEJMUTF-UHFFFAOYSA-N 0.000 description 1
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 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
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- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
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- 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
- 230000001629 suppression Effects 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
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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
- 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
- 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
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
- C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal
-
- 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
Abstract
本發明之目的在於提供一種遮光部硬化性優異、且可抑制液晶污染之液晶顯示元件用密封劑。又，本發明之目的在於提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 The object of the present invention is to provide a sealing compound for a liquid crystal display element which is excellent in curability of a light-shielding part and can suppress liquid crystal contamination. In addition, an object of the present invention is to provide an upper and lower conduction material and a liquid crystal display element using this sealing compound for liquid crystal display elements.
一種液晶顯示元件用密封劑，含有硬化性樹脂與光自由基聚合起始劑，上述硬化性樹脂含有分子量為100以上且未達500之化合物與分子量為500~3000之化合物，上述光自由基聚合起始劑為具有咔唑骨架之化合物。 A sealant for liquid crystal display elements, comprising a curable resin and a photo-radical polymerization initiator. The curable resin contains a compound with a molecular weight of 100 or more and less than 500 and a compound with a molecular weight of 500-3000. The photo-radical polymerization The initiator is a compound having a carbazole skeleton.
Description
本發明係關於一種遮光部硬化性優異、且可抑制液晶污染之液晶顯示元件用密封劑。又，本發明係關於一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 The present invention relates to a sealing compound for a liquid crystal display element which has excellent curability of a light-shielding portion and can suppress liquid crystal contamination. In addition, the present invention relates to an upper and lower conduction material and a liquid crystal display element using this sealant for liquid crystal display elements.
近年來，作為液晶顯示單元等液晶顯示元件之製造方法，就縮短產距時間、使用液晶量之最佳化之觀點而言，使用如專利文獻1、專利文獻2所揭示之被稱為滴加法之液晶滴加方式，該滴加法使用了含有硬化性樹脂、光聚合起始劑及熱硬化劑之光熱併用硬化型密封劑。 In recent years, as a method for manufacturing liquid crystal display elements such as liquid crystal display units, from the viewpoint of shortening the pitch time and optimizing the amount of liquid crystal used, the method known as the dripping method as disclosed in Patent Document 1 and Patent Document 2 is used. The liquid crystal dropping method, the dropping method uses a light-heat combination curing type sealing agent containing a curable resin, a photopolymerization initiator and a thermosetting agent.
關於滴加法，首先，於2片附電極透明基板之一者藉由滴塗而形成長方形狀之密封圖案。繼而，於密封劑未硬化之狀態向透明基板之框內整個面滴加液晶之微小滴，立即重疊另一透明基板，並朝密封部照射紫外線等光而進行暫時硬化。然後，於液晶退火時加熱而進行正式硬化，從而製作液晶顯示元件。若於減壓下進行基板之貼合，則能以極高之效率製造液晶顯示元件，目前該滴加法正成為液晶顯示元件之製造方法的主流。 Regarding the dropping method, first, a rectangular sealing pattern is formed by dropping on one of the two transparent substrates with electrodes. Then, in a state where the sealant is not hardened, droplets of liquid crystal are added to the entire surface of the frame of the transparent substrate, and the other transparent substrate is immediately superimposed, and the sealing portion is irradiated with light such as ultraviolet rays for temporary hardening. Then, heating is performed during the annealing of the liquid crystal to perform main curing, thereby producing a liquid crystal display element. If the substrates are bonded under reduced pressure, the liquid crystal display element can be manufactured with extremely high efficiency. At present, the dropping method is becoming the mainstream of the manufacturing method of the liquid crystal display element.
且說，於行動電話、攜帶型遊戲機等各種附液晶面板之移動機器日益普及之現代，裝置之小型化為最受關注之課題。作為裝置之小型 化的方法，可列舉液晶顯示部之窄邊緣化，例如，將密封部之位置配置於黑矩陣下(以下，亦稱為窄邊緣設計)。 In addition, in the modernization of mobile devices with LCD panels such as mobile phones, portable game consoles, etc., the miniaturization of the devices has become the most concerned topic. Small as a device The method of modification includes narrowing the edge of the liquid crystal display part, for example, arranging the position of the sealing part under the black matrix (hereinafter, also referred to as narrow-edge design).
然而，於窄邊緣設計中，由於密封劑被配置於黑矩陣之正下方，故而存在如下問題：當進行滴加法時，使密封劑光硬化時所照射之光被遮擋，光未到達密封劑之內部，硬化變得不充分。若如此密封劑之硬化變得不充分，則存在如下問題：未硬化之密封劑成分溶出至液晶中，溶出之密封劑成分所引起之硬化反應於液晶中進行，因而產生液晶污染。 However, in the narrow-edge design, since the sealant is arranged directly under the black matrix, there is a problem that when the dripping method is performed, the light irradiated when the sealant is hardened by light is blocked, and the light does not reach the sealant. Inside, hardening becomes insufficient. If the curing of the sealant becomes insufficient in this way, there is a problem that the uncured sealant component is eluted into the liquid crystal, and the curing reaction caused by the eluted sealant component proceeds in the liquid crystal, which causes liquid crystal contamination.
作為抑制液晶污染之方法，於專利文獻3中揭示有向密封劑摻合高感度之光聚合起始劑之內容。然而，若僅摻合高感度之光聚合起始劑，則無法於遮光部充分地抑制液晶污染。 As a method of suppressing liquid crystal contamination, Patent Document 3 discloses the content of blending a highly sensitive photopolymerization initiator to the sealant. However, if only a high-sensitivity photopolymerization initiator is blended, liquid crystal contamination cannot be sufficiently suppressed in the light-shielding portion.
專利文獻1：日本專利特開2001-133794號公報 Patent Document 1: Japanese Patent Laid-Open No. 2001-133794
專利文獻2：國際公開第02/092718號 Patent Document 2: International Publication No. 02/092718
專利文獻3：國際公開第2012/002028號 Patent Document 3: International Publication No. 2012/002028
本發明之目的在於提供一種遮光部硬化性優異、且可抑制液晶污染之液晶顯示元件用密封劑。又，本發明之目的在於提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 The object of the present invention is to provide a sealing compound for a liquid crystal display element which is excellent in curability of a light-shielding part and can suppress liquid crystal contamination. In addition, an object of the present invention is to provide an upper and lower conduction material and a liquid crystal display element using this sealing compound for liquid crystal display elements.
本發明係一種液晶顯示元件用密封劑，含有硬化性樹脂與光 自由基聚合起始劑，上述硬化性樹脂含有分子量為100以上且未達500之化合物與分子量為500~3000之化合物，上述光自由基聚合起始劑為具有咔唑骨架之化合物。 The present invention is a sealant for liquid crystal display elements, which contains curable resin and light A radical polymerization initiator, the curable resin contains a compound having a molecular weight of 100 or more and less than 500 and a compound having a molecular weight of 500 to 3000, and the photo radical polymerization initiator is a compound having a carbazole skeleton.
以下詳細敍述本發明。 The present invention will be described in detail below.
本發明人對如下情況進行了研究，即，為了提高密封劑之遮光部硬化性，使用具有咔唑骨架之化合物作為特別高感度之光自由基聚合起始劑。然而，即便使用此種光自由基聚合起始劑，亦存在遮光部硬化性不充分、容易產生液晶污染之問題。本發明人考慮到雖然作為光自由基聚合起始劑使用之具有咔唑骨架的化合物為高感度，但因對硬化性樹脂之溶解性低，故而無法充分提高遮光部硬化性。因此，本發明人發現，藉由不僅使用具有咔唑骨架之化合物作為光自由基聚合起始劑，進而將特定分子量之化合物組合而作為硬化性樹脂使用，可獲得遮光部硬化性優異、且可抑制液晶污染之液晶顯示元件用密封劑，從而完成了本發明。 The inventors of the present invention conducted studies on the use of a compound having a carbazole skeleton as a particularly high-sensitivity photo radical polymerization initiator in order to improve the curability of the light-shielding portion of the sealant. However, even if this kind of radical photopolymerization initiator is used, the curability of the light-shielding part is insufficient, and liquid crystal contamination is likely to occur. The present inventors considered that although the compound having a carbazole skeleton used as a radical photopolymerization initiator is highly sensitive, it cannot sufficiently improve the curability of the light-shielding portion due to its low solubility in the curable resin. Therefore, the present inventors found that by not only using a compound having a carbazole skeleton as a photoradical polymerization initiator, but also combining a compound with a specific molecular weight as a curable resin, it is possible to obtain excellent curability of the light-shielding part, and The sealing compound for liquid crystal display elements which suppresses liquid crystal contamination, and completed this invention.
本發明之液晶顯示元件用密封劑含有硬化性樹脂。 The sealing compound for liquid crystal display elements of this invention contains a curable resin.
上述硬化性樹脂含有分子量為100以上且未達500之化合物與分子量為500~3000之化合物。藉由將上述分子量為100以上且未達500之化合物與上述分子量為500~3000之化合物組合而使用，可使作為光自由基聚合起始劑之具有咔唑骨架之化合物充分地溶解，其結果為，本發明之液晶顯示元件用密封劑之遮光部硬化性優異，且可抑制液晶污染。 The above-mentioned curable resin contains a compound with a molecular weight of 100 or more and less than 500 and a compound with a molecular weight of 500 to 3000. By combining the above-mentioned compound with a molecular weight of 100 or more and less than 500 and the above-mentioned compound with a molecular weight of 500 to 3000, the compound having a carbazole skeleton as a photoradical polymerization initiator can be sufficiently dissolved, as a result Therefore, the sealing compound for liquid crystal display elements of the present invention has excellent curability of the light-shielding portion and can suppress liquid crystal contamination.
再者，於本說明書中，關於上述「分子量」，對於特定出分子結構之化合物為由結構式所求得之分子量，但對於聚合度之分佈較廣之化合物及改質部位不特定之化合物，有使用重量平均分子量表示之情形。於本說明書 中，上述「重量平均分子量」係利用凝膠滲透層析法(GPC)進行測定並藉由聚苯乙烯換算所求得之值。作為藉由GPC測定聚苯乙烯換算所得之重量平均分子量時所使用的管柱，例如可列舉Shodex LF-804(昭和電工公司製造)等。 Furthermore, in this specification, the above-mentioned "molecular weight" refers to the molecular weight obtained from the structural formula for a compound with a specific molecular structure, but for a compound with a wider degree of polymerization and a compound with an unspecified modification site, There are cases where the weight average molecular weight is used. In this manual Here, the above-mentioned "weight average molecular weight" is a value calculated by polystyrene conversion measured by gel permeation chromatography (GPC). As a column used when measuring the weight average molecular weight obtained by GPC conversion of polystyrene, Shodex LF-804 (manufactured by Showa Denko Corporation) etc. are mentioned, for example.
上述硬化性樹脂含有上述分子量為100以上且未達500之化合物。 The curable resin contains a compound having a molecular weight of 100 or more and less than 500.
關於上述分子量為100以上且未達500之化合物，就具有咔唑骨架之化合物之溶解性的觀點而言，較佳為分子量為300以上且未達500。 Regarding the compound having a molecular weight of 100 or more and less than 500, from the viewpoint of the solubility of the compound having a carbazole skeleton, the molecular weight is preferably 300 or more and less than 500.
上述硬化性樹脂較佳為含有(甲基)丙烯酸化合物作為上述分子量為100以上且未達500之化合物。 The curable resin preferably contains a (meth)acrylic compound as the compound having a molecular weight of 100 or more and less than 500.
作為上述(甲基)丙烯酸化合物，例如可列舉藉由使(甲基)丙烯酸與具有羥基之化合物進行反應所獲得之(甲基)丙烯酸酯化合物、藉由使(甲基)丙烯酸與環氧化合物進行反應所獲得之環氧(甲基)丙烯酸酯、藉由使異氰酸酯化合物與具有羥基之(甲基)丙烯酸衍生物進行反應所獲得之(甲基)丙烯酸胺基甲酸酯等。其中，較佳為環氧(甲基)丙烯酸酯。又，關於上述(甲基)丙烯酸化合物，就反應性高而言較佳為於1分子中具有2個以上之(甲基)丙烯醯基者。再者，於本說明書中，上述「(甲基)丙烯酸」意指丙烯酸或甲基丙烯酸，上述「(甲基)丙烯酸化合物」意指具有丙烯醯基或甲基丙烯醯基(以下，亦稱為「(甲基)丙烯醯基」)之化合物。又，上述「(甲基)丙烯酸酯」意指丙烯酸酯或甲基丙烯酸酯。進而，上述「環氧(甲基)丙烯酸酯」表示使環氧化合物中之全部環氧基與(甲基)丙烯酸進行反應而成之化合物。 Examples of the above-mentioned (meth)acrylic compound include (meth)acrylic acid ester compounds obtained by reacting (meth)acrylic acid with a compound having a hydroxyl group, and (meth)acrylic acid compounds obtained by reacting (meth)acrylic acid with epoxy compounds. Epoxy (meth)acrylate obtained by the reaction, (meth)acrylate urethane obtained by reacting an isocyanate compound with a (meth)acrylic acid derivative having a hydroxyl group, etc. Among them, epoxy (meth)acrylate is preferred. In addition, the (meth)acrylic compound described above is preferably one having two or more (meth)acrylic groups in one molecule in terms of high reactivity. In addition, in this specification, the above-mentioned "(meth)acrylic acid" means acrylic acid or methacrylic acid, and the above-mentioned "(meth)acrylic acid compound" means having an acrylic group or a methacrylic acid group (hereinafter also referred to as It is a compound of "(meth)acryloyl"). In addition, the above-mentioned "(meth)acrylate" means acrylate or methacrylate. Furthermore, the above-mentioned "epoxy (meth)acrylate" means a compound obtained by reacting all epoxy groups in an epoxy compound with (meth)acrylic acid.
作為上述(甲基)丙烯酸酯化合物中之單官能者，例如可列 舉：(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸異癸酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸異肉豆蔻酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸二環戊烯酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸2-乙氧基乙酯、(甲基)丙烯酸2-丁氧基乙酯、(甲基)丙烯酸2-苯氧基乙酯、甲氧基乙二醇(甲基)丙烯酸酯、苯氧基二乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸四氫呋喃甲酯、乙基卡必醇(甲基)丙烯酸酯、(甲基)丙烯酸2,2,2-三氟乙酯、(甲基)丙烯酸2,2,3,3-四氟丙酯、(甲基)丙烯酸1H,1H,5H-八氟戊酯、醯亞胺(甲基)丙烯酸酯、(甲基)丙烯酸二甲胺基乙酯、(甲基)丙烯酸二乙胺基乙酯、2-(甲基)丙烯醯氧基乙基琥珀酸、2-(甲基)丙烯醯氧基乙基六氫鄰苯二甲酸、2-羥基丙基鄰苯二甲酸2-(甲基)丙烯醯氧基乙酯、2-(甲基)丙烯醯氧基乙基磷酸酯、(甲基)丙烯酸縮水甘油酯等。 As the monofunctional among the above-mentioned (meth)acrylate compounds, for example, For example: methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, first (meth)acrylate Tributyl ester, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, isodecyl (meth)acrylate Esters, lauryl (meth)acrylate, isomyristyl (meth)acrylate, stearyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate , 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentene (meth)acrylate Ester, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 2-butoxyethyl (meth)acrylate, ( 2-phenoxy ethyl meth)acrylate, methoxy glycol (meth) acrylate, phenoxy diethylene glycol (meth) acrylate, methyl tetrahydrofuran (meth) acrylate, ethyl Carbitol (meth)acrylate, (meth)acrylate 2,2,2-trifluoroethyl, (meth)acrylate 2,2,3,3-tetrafluoropropyl, (meth)acrylate 1H ,1H,5H-octafluoropentyl ester, imine (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, 2-(methyl) Acrylic oxyethyl succinic acid, 2-(meth) acryloxy ethyl hexahydrophthalic acid, 2-hydroxypropyl phthalic acid 2-(meth) acryloxy ethyl, 2-(meth)acryloyloxyethyl phosphate, glycidyl (meth)acrylate, etc.
又，作為上述(甲基)丙烯酸酯化合物中之雙官能者，例如可列舉：1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、2-正丁基-2-乙基-1,3-丙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、二羥甲基二環戊二烯基二(甲基)丙烯酸酯、環氧乙烷改質異三聚氰酸二 (甲基)丙烯酸酯、2-羥基-3-(甲基)丙烯醯氧基丙基(甲基)丙烯酸酯、碳酸酯二醇二(甲基)丙烯酸酯等。 In addition, examples of the bifunctional ones in the (meth)acrylate compounds include 1,3-butanediol di(meth)acrylate and 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 two (Meth) acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, 2-n-butyl-2-ethyl-1,3-propanediol bis(meth) Base) acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, dimethylol dicyclopentadienyl bis(meth) Base) acrylate, ethylene oxide modified isocyanuric acid (Meth)acrylate, 2-hydroxy-3-(meth)acryloxypropyl (meth)acrylate, carbonate diol di(meth)acrylate, etc.
又，作為上述(甲基)丙烯酸酯化合物中之3官能以上者，例如可列舉：三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、三(甲基)丙烯醯氧基乙基磷酸酯、新戊四醇四(甲基)丙烯酸酯等。 In addition, examples of the tri- or more functional (meth)acrylate compounds include trimethylolpropane tri(meth)acrylate, ethylene oxide addition trimethylolpropane tri(methyl) )Acrylate, glycerol tri(meth)acrylate, neopentylerythritol tri(meth)acrylate, tri(meth)acryloyloxyethyl phosphate, neopenteritol tetra(meth)acrylate Wait.
作為上述環氧(甲基)丙烯酸酯，例如可列舉藉由依據常規方法於鹼性觸媒之存在下使環氧化合物與(甲基)丙烯酸進行反應所獲得者等。 As said epoxy (meth)acrylate, the thing obtained by reacting an epoxy compound and (meth)acrylic acid in the presence of a basic catalyst according to a conventional method, etc. are mentioned, for example.
作為成為用以合成上述環氧(甲基)丙烯酸酯之原料的環氧化合物，例如可列舉：雙酚A二環氧丙基醚、雙酚F二環氧丙基醚、雙酚E二環氧丙基醚、氫化雙酚A二環氧丙基醚、氫化雙酚F二環氧丙基醚、氫化雙酚E二環氧丙基醚、間苯二酚二環氧丙基醚、聯苯-4,4,-二基雙(環氧丙基醚)、1,6-萘二基雙(環氧丙基醚)、乙二醇二環氧丙基醚、1,3-丙二醇二環氧丙基醚、1,4-丁二醇二環氧丙基醚等。 As the epoxy compound used as a raw material for synthesizing the epoxy (meth)acrylate, for example, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol E bicyclic Hydroxypropyl ether, hydrogenated bisphenol A diglycidyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated bisphenol E diglycidyl ether, resorcinol diglycidyl ether, Benzene-4,4,-diyl bis (glycidyl ether), 1,6-naphthalenediyl bis (glycidyl ether), ethylene glycol diglycidyl ether, 1,3-propylene glycol two Glycidyl ether, 1,4-butanediol diglycidyl ether, etc.
作為上述藉由使異氰酸酯化合物與具有羥基之(甲基)丙烯酸衍生物進行反應所獲得之(甲基)丙烯酸胺基甲酸酯，例如可藉由使具有2個異氰酸基之異氰酸酯化合物1當量與具有羥基之(甲基)丙烯酸衍生物2當量，於觸媒量之錫系化合物存在下進行反應而獲得。 As the (meth)acrylate urethane obtained by reacting an isocyanate compound with a (meth)acrylic acid derivative having a hydroxyl group, for example, an isocyanate compound having two isocyanate groups 1 The equivalent is obtained by reacting 2 equivalents with a (meth)acrylic acid derivative having a hydroxyl group in the presence of a catalytic amount of a tin-based compound.
作為成為上述(甲基)丙烯酸胺基甲酸酯之原料的異氰酸酯化合物，例如可列舉：異佛爾酮二異氰酸酯、2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、六亞甲基二異氰酸酯、三甲基六亞甲基二異氰酸酯、二苯甲烷-4,4,-二異氰酸酯(MDI)、氫化MDI、1,5-萘二異氰酸酯、降
作為成為上述(甲基)丙烯酸胺基甲酸酯之原料之具有羥基的(甲基)丙烯酸衍生物，例如可列舉：(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸4-羥基丁酯等(甲基)丙烯酸羥基烷基酯、或乙二醇、丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇等二元醇之單(甲基)丙烯酸酯等。 Examples of the (meth)acrylic acid derivative having a hydroxyl group used as the raw material of the (meth)acrylic urethane include: 2-hydroxyethyl (meth)acrylate and 2-hydroxy (meth)acrylate Propyl ester, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate and other hydroxyalkyl (meth)acrylates, or ethylene glycol, propylene glycol, 1,3-propanediol, 1, Mono(meth)acrylates of diols such as 3-butanediol and 1,4-butanediol.
關於上述硬化性樹脂，就接著性及具有咔唑骨架之化合物之溶解性的觀點而言，較佳含有環氧化合物作為上述分子量為100以上且未達500之化合物。 Regarding the curable resin, it is preferable to contain an epoxy compound as the compound having a molecular weight of 100 or more and less than 500 from the viewpoint of adhesiveness and solubility of the compound having a carbazole skeleton.
作為上述環氧化合物，例如可列舉成為用以合成上述環氧(甲基)丙烯酸酯之原料之環氧化合物、或部分(甲基)丙烯酸改質環氧樹脂等。 As said epoxy compound, the epoxy compound used as a raw material for synthesizing the said epoxy (meth)acrylate, or a partially (meth)acrylic modified epoxy resin etc. are mentioned, for example.
再者，於本說明書中，上述部分(甲基)丙烯酸改質環氧樹脂意指於1分子中分別具有1個以上之環氧基及(甲基)丙烯醯基的化合物，例如可藉由使2種以上之環氧化合物之一部分環氧基與(甲基)丙烯酸進行反應而獲得。 Furthermore, in this specification, the above-mentioned partial (meth)acrylic modified epoxy resin means a compound having at least one epoxy group and (meth)acryloyl group in one molecule, for example, It is obtained by reacting one part of epoxy groups of two or more epoxy compounds with (meth)acrylic acid.
上述硬化性樹脂含有上述分子量為500~3000之化合物。上述分子量為500~3000之化合物之分子量較佳的下限為600，較佳之上限為2500。藉由上述分子量為500~3000之化合物的分子量為600以上，具有咔唑骨架之化合物的溶解性更加優異。藉由上述分子量為500~3000之化合物的分子量為2500以下，所獲得之液晶顯示元件用密封劑的低液晶污染性更加優異。上述分子量為500~3000之化合物之分子量更佳的下限為1000，更佳之上限為2000。 The said curable resin contains the said compound with a molecular weight of 500-3000. The preferred lower limit of the molecular weight of the compound having a molecular weight of 500-3000 is 600, and the preferred upper limit is 2500. Since the molecular weight of the compound having a molecular weight of 500 to 3000 is 600 or more, the solubility of the compound having a carbazole skeleton is more excellent. When the molecular weight of the compound having a molecular weight of 500 to 3000 is 2500 or less, the obtained sealing compound for liquid crystal display elements is more excellent in low liquid crystal contamination. The lower limit of the molecular weight of the compound having a molecular weight of 500-3000 is more preferably 1,000, and the more preferable upper limit is 2,000.
作為上述分子量為500~3000之化合物，較佳為低聚物化合物，更佳為聚合度為3~6之低聚物化合物。 As the above-mentioned compound having a molecular weight of 500 to 3000, an oligomer compound is preferred, and an oligomer compound having a polymerization degree of 3 to 6 is more preferred.
又，上述分子量為500~3000之化合物較佳為於1分子中具有合計2個以上之環氧基及/或(甲基)丙烯醯基之多官能化合物，就交聯密度提高、可進一步抑制溶出之方面而言，更佳為具有如酚醛清漆型結構之梳形結構的多官能化合物。 In addition, the above-mentioned compound having a molecular weight of 500 to 3000 is preferably a polyfunctional compound having a total of 2 or more epoxy groups and/or (meth)acrylic groups in one molecule, which can increase the crosslinking density and can further suppress In terms of elution, it is more preferably a polyfunctional compound having a comb-shaped structure such as a novolak-type structure.
作為上述分子量為500~3000之化合物，具體而言例如可列舉：酚系酚醛清漆型環氧樹脂、鄰甲酚酚醛清漆型環氧樹脂、二環戊二烯酚醛清漆型環氧樹脂、聯苯酚醛清漆型環氧樹脂、萘酚酚醛清漆型環氧樹脂、雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚E型環氧樹脂、雙酚S型環氧樹脂、2,22,-二烯丙基雙酚A型環氧樹脂、氫化雙酚型環氧樹脂、環氧丙烷加成雙酚A型環氧樹脂、間苯二酚型環氧樹脂、聯苯型環氧樹脂、硫醚型環氧樹脂、二苯醚型環氧樹脂、二環戊二烯型環氧樹脂、萘型環氧樹脂、縮水甘油胺型環氧樹脂、烷基多元醇型環氧樹脂、橡膠改質型環氧樹脂等低聚物型環氧樹脂、或者使該等低聚物型環氧樹脂與(甲基)丙烯酸進行反應而成之低聚物型環氧(甲基)丙烯酸酯或低聚物型部分(甲基)丙烯酸改質環氧樹脂等。其中，較佳為低聚物型環氧(甲基)丙烯酸酯。 Specific examples of the compound having a molecular weight of 500 to 3000 include: phenol novolac type epoxy resin, o-cresol novolac type epoxy resin, dicyclopentadiene novolac type epoxy resin, and biphenol Aldehyde type epoxy resin, naphthol novolak type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol S type epoxy resin, 2, 22'-Diallyl bisphenol A epoxy resin, hydrogenated bisphenol epoxy resin, propylene oxide addition bisphenol A epoxy resin, resorcinol epoxy resin, biphenyl epoxy resin Resin, thioether type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, glycidylamine type epoxy resin, alkyl polyol type epoxy resin, Oligomer epoxy resins such as rubber-modified epoxy resins, or oligomer epoxy (meth)acrylates formed by reacting these oligomeric epoxy resins with (meth)acrylic acid Or oligomer type partially (meth)acrylic modified epoxy resin, etc. Among them, oligomer type epoxy (meth)acrylate is preferred.
上述分子量為100以上且未達500之化合物與上述分子量為500~3000之化合物之合計100重量份中之上述分子量為500~3000之化合物含量的較佳下限為10重量份，較佳之上限為30重量份。藉由上述分子量為500~3000之化合物的含量為該範圍，所獲得之液晶顯示元件用密封劑之遮光部硬化性及抑制液晶污染的效果更加優異。上述分子量為500~3000 之化合物含量的更佳下限為12重量份，更佳之上限為20重量份。 The preferred lower limit of the content of the compound with a molecular weight of 500-3000 in 100 parts by weight of the total of the compound with a molecular weight of 100 or more and less than 500 and the compound with a molecular weight of 500-3000 is 10 parts by weight, and the preferred upper limit is 30 Parts by weight. When the content of the compound having a molecular weight of 500 to 3000 is in this range, the curability of the light-shielding portion of the sealant for liquid crystal display elements obtained and the effect of suppressing liquid crystal contamination are more excellent. The above molecular weight is 500~3000 The lower limit of the compound content is more preferably 12 parts by weight, and the upper limit is more preferably 20 parts by weight.
本發明之液晶顯示元件用密封劑含有光自由基聚合起始劑。 The sealing compound for liquid crystal display elements of this invention contains an optical radical polymerization initiator.
上述光自由基聚合起始劑為具有咔唑骨架之化合物。藉由使用上述具有咔唑骨架之化合物作為上述光自由基聚合起始劑，本發明之液晶顯示元件用密封劑之遮光部硬化性優異。 The above-mentioned radical photopolymerization initiator is a compound having a carbazole skeleton. By using the compound having the carbazole skeleton as the photoradical polymerization initiator, the sealing compound for liquid crystal display elements of the present invention has excellent curability of the light-shielding portion.
上述具有咔唑骨架之化合物分子量的較佳下限為300，較佳之上限為1000。藉由上述具有咔唑骨架之化合物的分子量為該範圍，於上述硬化性樹脂中之溶解性更加優異。上述具有咔唑骨架之化合物分子量的更佳下限為400，更佳之上限為700。 The preferred lower limit of the molecular weight of the compound having a carbazole skeleton is 300, and the preferred upper limit is 1,000. When the molecular weight of the compound having a carbazole skeleton is in this range, the solubility in the curable resin is more excellent. The lower limit of the molecular weight of the compound having a carbazole skeleton is more preferably 400, and the upper limit is more preferably 700.
關於上述具有咔唑骨架之化合物，就對上述硬化性樹脂中之溶解性的觀點而言，較佳為具有咔唑骨架所含有之芳香環以外的芳香環。 With regard to the compound having a carbazole skeleton, it is preferable to have an aromatic ring other than the aromatic ring contained in the carbazole skeleton from the viewpoint of solubility in the curable resin.
又，關於上述具有咔唑骨架之化合物，就遮光部硬化性更加優異之方面而言，較佳為具有咔唑骨架所含有之氮原子以外的氮原子，更佳為具有肟酯鍵。 Moreover, regarding the compound having a carbazole skeleton, it is preferable to have a nitrogen atom other than the nitrogen atom contained in the carbazole skeleton, and it is more preferable to have an oxime ester bond from the viewpoint that the light-shielding portion is more excellent in curability.
上述具有咔唑骨架之化合物較佳為以濃度成為0.1mg/mL之方式混合有該具有咔唑骨架之化合物之乙腈中所測定之波長365nm的吸光係數為50mL/g．cm以上。藉由上述具有咔唑骨架之化合物的吸光係數為50mL/g．cm以上，所獲得之液晶顯示元件用密封劑之遮光部硬化性更加優異。上述具有咔唑骨架之化合物的吸光係數更佳為100mL/g．cm以上。 The compound having the carbazole skeleton is preferably mixed with the compound having the carbazole skeleton at a concentration of 0.1 mg/mL. The absorption coefficient measured at a wavelength of 365 nm in acetonitrile is 50 mL/g. cm above. The absorption coefficient of the above compound with a carbazole skeleton is 50 mL/g. cm or more, the obtained sealing compound for liquid crystal display elements has more excellent light-shielding part curability. The absorption coefficient of the compound having a carbazole skeleton is more preferably 100 mL/g. cm above.
又，上述具有咔唑骨架之化合物之吸光係數的較佳上限並無特別限制，實質之上限為1000mL/g．cm。 In addition, the preferred upper limit of the absorption coefficient of the compound having a carbazole skeleton is not particularly limited, and the actual upper limit is 1000 mL/g. cm.
作為上述具有咔唑骨架之化合物，具體而言，例如可列
舉：O-乙醯基-1-(6-(2-甲基苯甲醯基)-9-乙基-9H-咔唑-3-基)乙酮肟、3,6-雙-(2-甲基-2-
作為上述具有咔唑骨架之化合物中的市售者，例如可列舉IRGACURE OXE02(BASF公司製造)等。 As a commercially available one among the above-mentioned compounds having a carbazole skeleton, for example, IRGACURE OXE02 (manufactured by BASF Corporation) and the like can be cited.
上述具有咔唑骨架之化合物的含量相對於上述硬化性樹脂100重量份之較佳下限為0.5重量份，較佳之上限為10重量份。藉由上述具有咔唑骨架之化合物的含量為該範圍，所獲得之液晶顯示元件用密封劑的遮光部硬化性、耐候性、保存穩定性、及抑制液晶污染之效果更加優異。上述具有咔唑骨架之化合物含量的更佳下限為1重量份，更佳之上限為3重量份。 A preferable lower limit of the content of the compound having a carbazole skeleton relative to 100 parts by weight of the curable resin is 0.5 parts by weight, and a preferable upper limit is 10 parts by weight. When the content of the compound having a carbazole skeleton is in this range, the obtained sealing compound for liquid crystal display elements has more excellent light-shielding portion curability, weather resistance, storage stability, and liquid crystal contamination suppression effect. The lower limit of the content of the compound having a carbazole skeleton is more preferably 1 part by weight, and the upper limit is more preferably 3 parts by weight.
關於本發明之液晶顯示元件用密封劑，除上述具有咔唑骨架之化合物，亦可含有其他光自由基聚合起始劑作為上述光自由基聚合起始劑，但就兼顧遮光部硬化性及抑制液晶污染之效果的觀點而言，較佳為不含其他光自由基聚合起始劑。 Regarding the sealing compound for liquid crystal display elements of the present invention, in addition to the above-mentioned compound having a carbazole skeleton, other photo-radical polymerization initiators may be contained as the above-mentioned photo-radical polymerization initiator, but both the light-shielding part hardenability and inhibition From the viewpoint of the effect of liquid crystal contamination, it is preferable that no other radical photopolymerization initiator is contained.
本發明之液晶顯示元件用密封劑亦可含有增感劑。 The sealing compound for liquid crystal display elements of this invention may contain a sensitizer.
本發明之液晶顯示元件用密封劑藉由含有上述增感劑，能以更高感度獲得遮光部硬化性優異之液晶顯示元件用密封劑。 The sealing compound for liquid crystal display elements of this invention contains the said sensitizer, and the sealing compound for liquid crystal display elements which is excellent in curability of a light-shielding part can be obtained with higher sensitivity.
關於上述增感劑，就較佳為於紫外線-可見光區域具有充分之光吸收帶之方面而言，較佳為選自由具有二苯甲酮骨架之化合物、具有
蒽骨架之化合物、具有蒽醌骨架之化合物、具有香豆素骨架之化合物、具有9-氧硫
作為上述具有二苯甲酮骨架之化合物，例如可列舉：二苯甲酮、2,4-二氯二苯甲酮、4,4,-雙(二甲胺基)二苯甲酮、4,4,-雙(二乙胺基)二苯甲酮等。 As the above-mentioned compound having a benzophenone skeleton, for example, benzophenone, 2,4-dichlorobenzophenone, 4,4,-bis(dimethylamino)benzophenone, 4, 4,-Bis(diethylamino)benzophenone, etc.
作為上述具有蒽骨架之化合物，例如可列舉；9,10-二乙氧基蒽、9,10-二丙氧基蒽、9,10-二丁氧基蒽等。 Examples of the above-mentioned compound having an anthracene skeleton include 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, 9,10-dibutoxyanthracene, and the like.
作為上述具有蒽醌骨架之化合物，例如可列舉：1-甲基蒽醌、2-乙基蒽醌、1,4-二羥基蒽醌、2-(2-羥基乙氧基)蒽醌等。 Examples of the compound having an anthraquinone skeleton include 1-methylanthraquinone, 2-ethylanthraquinone, 1,4-dihydroxyanthraquinone, 2-(2-hydroxyethoxy)anthraquinone, and the like.
作為上述具有香豆素骨架之化合物，例如可列舉7-二乙胺基-4-甲基香豆素等。 Examples of the compound having a coumarin skeleton include 7-diethylamino-4-methylcoumarin and the like.
作為上述具有9-氧硫
作為上述具有酞菁骨架之化合物，例如可列舉酞菁等。 Examples of the compound having a phthalocyanine skeleton include phthalocyanine.
該等增感劑之中，就所獲得之液晶顯示元件用密封劑之遮光部硬化性特別優異之方面而言，較佳為4,4'-雙(二甲胺基)二苯甲酮及4,4'-雙(二乙胺基)二苯甲酮之至少一者。 Among these sensitizers, 4,4'-bis(dimethylamino)benzophenone and 4,4'-bis(dimethylamino)benzophenone and the light-shielding portion of the obtained sealant for liquid crystal display elements are particularly excellent. At least one of 4,4'-bis(diethylamino)benzophenone.
上述增感劑之含量相對於上述光自由基聚合起始劑100重量份之較佳下限為2重量份，較佳之上限為50重量份。藉由上述增感劑之 含量為該範圍，抑制了液晶污染，並且所獲得之液晶顯示元件用密封劑的遮光部硬化性更加優異。上述增感劑含量之更佳下限為5重量份，更佳之上限為40重量份。 The lower limit of the content of the sensitizer relative to 100 parts by weight of the photo radical polymerization initiator is preferably 2 parts by weight, and the upper limit is preferably 50 parts by weight. By the above sensitizer When the content is in this range, liquid crystal contamination is suppressed, and the obtained sealing compound for liquid crystal display elements has more excellent light-shielding portion curability. The lower limit of the content of the sensitizer is more preferably 5 parts by weight, and the upper limit is more preferably 40 parts by weight.
本發明之液晶顯示元件用密封劑亦可含有熱自由基聚合起始劑。 The sealing compound for liquid crystal display elements of this invention may contain a thermal radical polymerization initiator.
作為上述熱自由基聚合起始劑，例如可列舉由偶氮化合物、有機過氧化物等構成者。其中，較佳為由高分子偶氮化合物構成之起始劑(以下，亦稱為「高分子偶氮起始劑」)。 Examples of the thermal radical polymerization initiator include those composed of azo compounds, organic peroxides, and the like. Among them, a starter composed of a polymer azo compound (hereinafter, also referred to as a "polymer azo starter") is preferred.
再者，於本說明書中，所謂高分子偶氮化合物意指具有偶氮基、由熱產生自由基之數量平均分子量為300以上的化合物。 In addition, in this specification, the term "polymer azo compound" means a compound having an azo group and having a number average molecular weight of 300 or more radicals generated by heat.
上述高分子偶氮起始劑之數量平均分子量的較佳下限為1000，較佳之上限為30萬。藉由上述高分子偶氮起始劑之數量平均分子量為該範圍，可抑制液晶污染，並且與硬化性樹脂容易地混合。上述高分子偶氮起始劑之數量平均分子量的更佳下限為5000，更佳之上限為10萬，進而較佳之下限為1萬，進而較佳之上限為9萬。 The preferred lower limit of the number average molecular weight of the above-mentioned polymer azo initiator is 1,000, and the preferred upper limit is 300,000. When the number average molecular weight of the polymer azo initiator is in this range, liquid crystal contamination can be suppressed, and it can be easily mixed with the curable resin. The lower limit of the number average molecular weight of the polymer azo initiator is more preferably 5,000, the upper limit is more preferably 100,000, the lower limit is more preferably 10,000, and the upper limit is more preferably 90,000.
再者，於本說明書中，上述數量平均分子量係利用凝膠滲透層析法(GPC)進行測定並藉由聚苯乙烯換算所求得之值。作為藉由GPC測定聚苯乙烯換算所得之數量平均分子量時之管柱，例如可列舉Shodex LF-804(昭和電工公司製造)等。 In addition, in this specification, the said number average molecular weight is the value calculated|required by the polystyrene conversion measured by gel permeation chromatography (GPC). As the column when the number average molecular weight obtained by GPC is measured in terms of polystyrene, for example, Shodex LF-804 (manufactured by Showa Denko Co., Ltd.) can be cited.
作為上述高分子偶氮起始劑，例如可列舉具有經由偶氮基而鍵結有複數個聚環氧烷或聚二甲基矽氧烷等單元之結構者。 Examples of the above-mentioned polymer azo initiator include those having a structure in which a plurality of units such as polyalkylene oxide or polydimethylsiloxane are bonded via an azo group.
作為上述具有經由偶氮基而鍵結有複數個聚環氧烷等單元之結構的高 分子偶氮起始劑，較佳為具有聚環氧乙烷結構者。作為此種高分子偶氮起始劑，例如可列舉：4,4,-偶氮雙(4-氰基戊酸)與聚伸烷基二醇之縮聚物、或4,4,-偶氮雙(4-氰基戊酸)與具有末端胺基之聚二甲基矽氧烷之縮聚物等，具體而言，例如可列舉：VPE-0201、VPE-0401、VPE-0601、VPS-0501、VPS-1001(均為和光純藥工業公司製造)等。又，作為並非高分子之偶氮化合物之例，可列舉V-65、V-501(均為和光純藥工業公司製造)等。 As the above-mentioned structure with multiple units such as polyalkylene oxide bonded via an azo group The molecular azo initiator is preferably one having a polyethylene oxide structure. As such a polymer azo initiator, for example, a condensation polymer of 4,4,-azobis(4-cyanovaleric acid) and polyalkylene glycol, or 4,4,-azo The polycondensate of bis(4-cyanovaleric acid) and polydimethylsiloxane having a terminal amine group, etc., specifically, for example: VPE-0201, VPE-0401, VPE-0601, VPS-0501 , VPS-1001 (all manufactured by Wako Pure Chemical Industries, Ltd.), etc. In addition, examples of azo compounds that are not polymers include V-65 and V-501 (all manufactured by Wako Pure Chemical Industries, Ltd.).
作為上述有機過氧化物，例如可列舉：過氧化酮、過氧縮酮、過氧化氫、過氧化二烷基、過氧化酯、過氧化二醯基、過氧化二碳酸酯等。 As said organic peroxide, for example, ketone peroxide, peroxyketal, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, peroxydicarbonate, etc. are mentioned.
上述熱自由基聚合起始劑之含量相對於硬化性樹脂100重量份之較佳下限為0.05重量份，較佳之上限為10重量份。藉由上述熱自由基聚合起始劑為該範圍，所獲得之液晶顯示元件用密封劑抑制了液晶污染，並且保存穩定性或硬化性更加優異。上述熱自由基聚合起始劑含量之更佳下限為0.1重量份，更佳之上限為5重量份。 The preferred lower limit of the content of the thermal radical polymerization initiator relative to 100 parts by weight of the curable resin is 0.05 parts by weight, and the preferred upper limit is 10 parts by weight. When the thermal radical polymerization initiator is in this range, the obtained sealing compound for liquid crystal display elements suppresses liquid crystal contamination and is more excellent in storage stability or curability. The lower limit of the content of the thermal radical polymerization initiator is more preferably 0.1 parts by weight, and the upper limit is more preferably 5 parts by weight.
本發明之液晶顯示元件用密封劑亦可含有熱硬化劑。 The sealing compound for liquid crystal display elements of this invention may contain a thermosetting agent.
作為上述熱硬化劑，例如可列舉：有機酸醯肼、咪唑衍生物、胺化合物、多酚系化合物、酸酐等。其中，適宜使用有機酸醯肼。 As said thermosetting agent, organic acid hydrazine, imidazole derivatives, amine compounds, polyphenol compounds, acid anhydrides, etc. are mentioned, for example. Among them, the organic acid hydrazine is suitably used.
作為上述有機酸醯肼，例如可列舉：癸二醯肼、間苯二甲酸二醯肼、己二醯肼、丙二醯肼等。 As said organic acid hydrazine, for example, sebacic hydrazine, isophthalic acid dihydrazine, hexadihydrazine, malondihydrazine, etc. are mentioned.
作為上述有機酸醯肼中之市售者，例如可列舉：SDH、ADH(均為大塚化學公司製造)、Amicure VDH、Amicure VDH-J、Amicure UDH、Amicure UDH-J(均為Ajinomoto Fine-Techno公司製造)等。 Examples of commercially available organic acid hydrazine include: SDH, ADH (all manufactured by Otsuka Chemical Co., Ltd.), Amicure VDH, Amicure VDH-J, Amicure UDH, and Amicure UDH-J (all are Ajinomoto Fine-Techno Company manufacturing) etc.
上述熱硬化劑之含量相對於上述硬化性樹脂100重量份之 較佳下限為1重量份，較佳之上限為50重量份。藉由上述熱硬化劑之含量為該範圍，可不使所獲得之液晶顯示元件用密封劑之塗佈性等變差而使熱硬化性更加優異。上述熱硬化劑之含量的更佳上限為30重量份。 The content of the thermosetting agent is relative to 100 parts by weight of the curable resin A preferred lower limit is 1 part by weight, and a preferred upper limit is 50 parts by weight. When the content of the thermosetting agent is in this range, it is possible to make the thermosetting properties more excellent without deteriorating the coating properties of the obtained sealing compound for liquid crystal display elements. The more preferable upper limit of the content of the thermal hardening agent is 30 parts by weight.
為了提高黏度、改善應力分散效果所決定之接著性、改善線膨脹率、進一步提高硬化物之耐濕性等，本發明之液晶顯示元件用密封劑較佳為含有填充劑。 In order to increase the viscosity, improve the adhesiveness determined by the stress dispersion effect, improve the linear expansion rate, and further improve the moisture resistance of the cured product, the sealing compound for liquid crystal display elements of the present invention preferably contains a filler.
作為上述填充劑，例如可列舉：氧化矽、滑石、玻璃珠、石棉、石膏、矽藻土、膨潤石、膨潤土、蒙脫石、絹雲母、活化黏土、氧化鋁、氧化鋅、氧化鐵、氧化鎂、氧化錫、氧化鈦、碳酸鈣、碳酸鎂、氫氧化鎂、氫氧化鋁、氮化鋁、氮化矽、硫酸鋇、矽酸鈣等無機填充劑、或聚酯微粒子、聚胺基甲酸酯微粒子、乙烯聚合物微粒子、丙烯酸聚合物微粒子等有機填充劑。 Examples of the above-mentioned filler include: silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, bentonite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, oxide Inorganic fillers such as magnesium, tin oxide, titanium oxide, calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate, etc., or polyester microparticles, polyurethane Organic fillers such as acid ester particles, ethylene polymer particles, and acrylic polymer particles.
本發明之液晶顯示元件用密封劑100重量份中之上述填充劑含量的較佳下限為10重量份，較佳之上限為70重量份。藉由上述填充劑之含量為該範圍，可不使塗佈性等變差而使接著性之改善等效果更加優異。上述填充劑含量的更佳下限為20重量份，更佳之上限為60重量份。 A preferable lower limit of the filler content in 100 parts by weight of the sealing compound for liquid crystal display elements of the present invention is 10 parts by weight, and a preferable upper limit is 70 parts by weight. When the content of the filler is in this range, it is possible to achieve more excellent effects such as improvement in adhesiveness without deteriorating coatability and the like. The lower limit of the filler content is more preferably 20 parts by weight, and the upper limit is more preferably 60 parts by weight.
本發明之液晶顯示元件用密封劑較佳為含有矽烷偶合劑。上述矽烷偶合劑主要具有作為用以將密封劑與基板等良好地接著之接著助劑的作用。 It is preferable that the sealing compound for liquid crystal display elements of this invention contains a silane coupling agent. The above-mentioned silane coupling agent mainly functions as an adhesive auxiliary agent for bonding the sealant to the substrate and the like well.
作為上述矽烷偶合劑，就提高與基板等之接著性的效果優異、可藉由與硬化性樹脂進行化學鍵結而抑制硬化性樹脂流出至液晶中之方面而言，例如適宜使用3-胺基丙基三甲氧基矽烷、3-巰基丙基三甲氧基矽 烷、3-環氧丙氧基丙基三甲氧基矽烷、3-異氰酸基丙基三甲氧基矽烷等。該等矽烷偶合劑可單獨使用，亦可將2種以上組合而使用。 As the above-mentioned silane coupling agent, it is excellent in the effect of improving the adhesion to the substrate, etc., and can inhibit the curable resin from flowing out into the liquid crystal by chemical bonding with the curable resin, for example, 3-aminopropyl is preferably used. Trimethoxysilane, 3-mercaptopropyltrimethoxysilane Alkyl, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, etc. These silane coupling agents may be used alone or in combination of two or more kinds.
本發明之液晶顯示元件用密封劑100重量份中之上述矽烷偶合劑含量的較佳下限為0.1重量份，較佳之上限為10重量份。藉由上述矽烷偶合劑之含量為該範圍，抑制了液晶污染之產生，並且使接著性提高之效果更加優異。上述矽烷偶合劑含量的更佳下限為0.3重量份，更佳之上限為5重量份。 The preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the sealing compound for liquid crystal display elements of the present invention is 0.1 parts by weight, and the preferable upper limit is 10 parts by weight. When the content of the silane coupling agent is in this range, the occurrence of liquid crystal contamination is suppressed, and the effect of improving adhesion is more excellent. 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.
本發明之液晶顯示元件用密封劑亦可含有遮光劑。藉由含有上述遮光劑，本發明之液晶顯示元件用密封劑可較佳地用作遮光密封劑。 The sealing compound for liquid crystal display elements of this invention may contain a light-shielding agent. By containing the said light-shielding agent, the sealing compound for liquid crystal display elements of this invention can be used suitably as a light-shielding sealing compound.
作為上述遮光劑，例如可列舉：氧化鐵、鈦黑、苯胺黑、花青黑、富勒烯、碳黑、樹脂被覆型碳黑等。其中，就絕緣性高之方面而言，較佳為鈦黑。 Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Among them, titanium black is preferred in terms of high insulation.
上述鈦黑即便為未經表面處理者亦發揮充分之效果，但亦可使用表面經偶合劑等有機成分進行處理者，或以氧化矽、氧化鈦、氧化鍺、氧化鋁、氧化鋯、氧化鎂等無機成分被覆者等經表面處理之鈦黑。其中，經有機成分處理者於可進一步提高絕緣性之方面而言較佳。 The above-mentioned titanium black exhibits sufficient effects even if it is not surface-treated, but the surface can be treated with organic ingredients such as coupling agent, or silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, magnesium oxide Surface-treated titanium black for those coated with other inorganic components. Among them, those treated with organic components are preferred in terms of further improving insulation.
又，使用含有上述鈦黑作為遮光劑之本發明的液晶顯示元件用密封劑所製造之液晶顯示元件具有充分之遮光性，因此可實現不存在光之洩漏、具有高對比度、具有優異之圖像顯示品質的液晶顯示元件。 In addition, the liquid crystal display element manufactured using the sealant for liquid crystal display elements of the present invention containing the titanium black as a light shielding agent has sufficient light shielding properties, and therefore can achieve no light leakage, high contrast, and excellent images. Display quality liquid crystal display element.
作為上述鈦黑中之市售者，例如可列舉：12S、13M、13M-C、13R-N、14M-C(均為三菱綜合材料公司製造)、Tilack D(赤穗化成公司製造)等。 Examples of commercially available titanium blacks include 12S, 13M, 13M-C, 13R-N, and 14M-C (all manufactured by Mitsubishi Materials Corporation), Tilack D (manufactured by Ako Chemical Co., Ltd.), and the like.
上述鈦黑之比表面積的較佳下限為13m2/g，較佳之上限為30m2/g，更佳之下限為15m2/g，更佳之上限為25m2/g。 The preferred lower limit of the specific surface area of the titanium black is 13 m 2 /g, the preferred upper limit is 30 m 2 /g, the more preferred lower limit is 15 m 2 /g, and the more preferred upper limit is 25 m 2 /g.
又，上述鈦黑之體積電阻的較佳下限為0.5Ω．cm，較佳之上限為3Ω．cm，更佳之下限為1Ω．cm，更佳之上限為2.5Ω．cm。 In addition, the preferred lower limit of the volume resistance of the titanium black is 0.5Ω. cm, the preferred upper limit is 3Ω. cm, the better lower limit is 1Ω. cm, a more preferable upper limit is 2.5Ω. cm.
上述遮光劑之一次粒徑只要為液晶顯示元件之基板間的距離以下則並無特別限定，較佳之下限為1nm，較佳之上限為5nm。藉由上述遮光劑之一次粒徑為該範圍，可不使所獲得之液晶顯示元件用密封劑的塗佈性等變差而使遮光性更加優異。上述遮光劑之一次粒徑的更佳下限5nm，更佳之上限為200nm，進而較佳之下限為10nm，進而較佳之上限為100nm。 The primary particle size of the light-shielding agent is not particularly limited as long as it is less than the distance between the substrates of the liquid crystal display element. The preferred lower limit is 1 nm, and the preferred upper limit is 5 nm. When the primary particle diameter of the said light-shielding agent is this range, the coating property etc. of the sealing compound for liquid crystal display elements obtained are not deteriorated, and light-shielding property can be made more excellent. The lower limit of the primary particle size of the sunscreen is more preferably 5 nm, the upper limit is more preferably 200 nm, the lower limit is still more preferably 10 nm, and the upper limit is still more preferably 100 nm.
再者，上述遮光劑之一次粒徑可使用NICOMP 380ZLS(PARTICLE SIZING SYSTEMS公司製造)，使上述遮光劑分散於溶劑(水、有機溶劑等)而進行測定。 In addition, the primary particle size of the sunscreen can be measured by dispersing the sunscreen in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICLE SIZING SYSTEMS).
本發明之液晶顯示元件用密封劑100重量份中之上述遮光劑之含量的較佳下限為5重量份，較佳之上限為80重量份。藉由上述遮光劑之含量為該範圍，可不使所獲得之液晶顯示元件用密封劑之對基板的密接性或者硬化後之強度或繪圖性降低而發揮更優異之遮光性。上述遮光劑之含量的更佳下限為10重量份，更佳之上限為70重量份，進而較佳之下限為30重量份，進而較佳之上限為60重量份。 A preferable lower limit of the content of the light-shielding agent in 100 parts by weight of the sealing compound for liquid crystal display elements of the present invention is 5 parts by weight, and a preferable upper limit is 80 parts by weight. When the content of the light-shielding agent is in this range, it is possible to exhibit more excellent light-shielding properties without lowering the adhesion of the obtained sealing compound for liquid crystal display elements to the substrate, or the strength or drawing properties after curing. The lower limit of the content of the sunscreen is more preferably 10 parts by weight, the upper limit is more preferably 70 parts by weight, the lower limit is still more preferably 30 parts by weight, and the upper limit is more preferably 60 parts by weight.
作為製造本發明之液晶顯示元件用密封劑的方法，例如可列舉使用均相分散機、均質攪拌機、萬能攪拌機、行星式攪拌機、捏合機、三輥研磨機等混合機將硬化性樹脂、光自由基聚合起始劑、及視需要添加 之矽烷偶合劑等添加劑混合之方法等。 As a method of manufacturing the sealant for liquid crystal display elements of the present invention, for example, the curable resin and the light are freed from mixing machines such as homogeneous dispersers, homomixers, universal mixers, planetary mixers, kneaders, and three-roll mills. Base polymerization initiator, and add as needed The method of mixing additives such as silane coupling agent, etc.
藉由向本發明之液晶顯示元件用密封劑摻合導電性微粒子，可製造上下導通材料。此種含有本發明之液晶顯示元件用密封劑與導電性微粒子之上下導通材料亦為本發明之一種。 By blending conductive fine particles into the sealing compound for liquid crystal display elements of the present invention, a vertical conduction material can be produced. Such an upper and lower conduction material containing the sealing compound for liquid crystal display elements of the present invention and conductive fine particles is also one of the present invention.
作為上述導電性微粒子，可使用金屬球、於樹脂微粒子之表面形成有導電金屬層者等。其中，於樹脂微粒子之表面形成有導電金屬層者因樹脂微粒子之優異彈性而能夠不使透明基板等受損地進行導電連接，就該方面而言較適宜。 As the conductive fine particles, metal balls, those having a conductive metal layer formed on the surface of resin fine particles, or the like can be used. Among them, those having a conductive metal layer formed on the surface of the resin fine particles are more suitable in this respect because of the excellent elasticity of the resin fine particles, which enables conductive connection without damaging the transparent substrate or the like.
使用本發明之液晶顯示元件用密封劑或本發明之上下導通材料而成之液晶顯示元件亦為本發明之一種。 The liquid crystal display element which uses the sealing compound for liquid crystal display elements of this invention or the top and bottom conduction material of this invention is also a kind of this invention.
作為製造本發明之液晶顯示元件的方法，適宜使用液晶滴加法。具體而言，例如可列舉如下方法等，該方法包括以下步驟：於附ITO薄膜等電極之玻璃基板或聚對苯二甲酸乙二酯基板等2片基板之一者，利用網版印刷、分注器塗佈等塗佈本發明之液晶顯示元件用密封劑而形成框狀之密封圖案；於本發明之液晶顯示元件用密封劑未硬化之狀態向基板之密封圖案的框內滴加塗佈液晶之微小滴，並於真空下重疊另一基板；及對本發明之液晶顯示元件用密封劑的密封圖案部分照射紫外線等光而使密封劑光硬化。又，除上述使密封劑光硬化之步驟外，亦可進行對密封劑加熱而使其熱硬化之步驟。 As a method of manufacturing the liquid crystal display element of the present invention, a liquid crystal dropping method is suitably used. Specifically, for example, the following method can be cited. The method includes the following steps: screen printing and separation on a glass substrate with electrodes such as an ITO film or a polyethylene terephthalate substrate. Injector coating, etc. apply the sealant for liquid crystal display elements of the present invention to form a frame-shaped seal pattern; in a state where the sealant for liquid crystal display elements of the present invention is not hardened, apply dropwise coating to the frame of the seal pattern of the substrate The minute drop of liquid crystal is superimposed on another substrate under vacuum; and the sealing pattern part of the sealing compound for liquid crystal display element of the present invention is irradiated with light such as ultraviolet rays to light-harden the sealing compound. Furthermore, in addition to the above-mentioned step of photocuring the sealant, a step of heating the sealant to thermally harden it may also be performed.
根據本發明，可提供一種遮光部硬化性優異、且可抑制液晶污染之液晶顯示元件用密封劑。又，根據本發明，可提供一種使用該液晶 顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 According to the present invention, it is possible to provide a sealing compound for a liquid crystal display element which is excellent in curability of a light-shielding portion and can suppress liquid crystal contamination. Moreover, according to the present invention, it is possible to provide a The sealing compound for display elements is a top and bottom conduction material and a liquid crystal display element.
以下揭示實施例而更詳細地說明本發明，但本發明並不僅限定於該等實施例。 Examples are disclosed below to illustrate the present invention in more detail, but the present invention is not limited to these examples.
(雙酚A型環氧丙烯酸酯A之合成) (Synthesis of bisphenol A epoxy acrylate A)
使雙酚A二環氧丙基醚(迪愛生公司製造，「EPICLONEXA-850CRP」)340g溶解於甲苯500mL之後，添加三苯膦0.1g製成均勻之溶液。於回流攪拌下耗時2小時向所獲得之溶液滴加丙烯酸144g後，進而進行8小時之回流攪拌。其次，藉由將甲苯去除而獲得雙酚A型環氧丙烯酸酯A。 After dissolving 340 g of bisphenol A diglycidyl ether (manufactured by DIC, "EPICLONEXA-850CRP") in 500 mL of toluene, 0.1 g of triphenylphosphine was added to make a uniform solution. After 144 g of acrylic acid was added dropwise to the obtained solution under reflux stirring for 2 hours, reflux stirring was further performed for 8 hours. Second, by removing toluene, bisphenol A epoxy acrylate A is obtained.
藉由1H-NMR、13C-NMR、LC-TOF/MS、及IR確認所獲得之雙酚A型環氧丙烯酸酯A為雙酚A二環氧丙基醚二丙烯酸酯(分子量484)。 Confirmed by 1 H-NMR, 13 C-NMR, LC-TOF/MS, and IR that the obtained bisphenol A epoxy acrylate A is bisphenol A diglycidyl ether diacrylate (molecular weight 484) .
(雙酚A型環氧丙烯酸酯B之合成) (Synthesis of bisphenol A epoxy acrylate B)
使雙酚A型環氧樹脂(三菱化學公司製造，「jER834」)500g溶解於甲苯500mL之後，添加三苯膦0.1g製成均勻之溶液。於回流攪拌下耗時2小時向所獲得之溶液滴加丙烯酸144g後，進而進行8小時之回流攪拌。其次，藉由將甲苯去除而獲得雙酚A型環氧丙烯酸酯B。 After dissolving 500 g of bisphenol A epoxy resin (manufactured by Mitsubishi Chemical Corporation, "jER834") in 500 mL of toluene, 0.1 g of triphenylphosphine was added to prepare a uniform solution. After 144 g of acrylic acid was added dropwise to the obtained solution under reflux stirring for 2 hours, reflux stirring was further performed for 8 hours. Second, by removing toluene, bisphenol A epoxy acrylate B is obtained.
藉由1H-NMR、13C-NMR、LC-TOF/MS、及IR確認所獲得之雙酚A型環氧丙烯酸酯B為分子量644之低聚物型環氧丙烯酸酯。 It was confirmed by 1 H-NMR, 13 C-NMR, LC-TOF/MS, and IR that the obtained bisphenol A epoxy acrylate B is an oligomer epoxy acrylate with a molecular weight of 644.
(實施例1~9、比較例1~5) (Examples 1 to 9, Comparative Examples 1 to 5)
依據表1、2所記載之摻合比，使用行星式攪拌機(新基公司製造，「去泡攪拌太郎」)將各材料混合之後，進而使用三輥研磨機進行混合，藉此製備實施例1~9、比較例1~5之液晶顯示元件用密封劑。 According to the blending ratios described in Tables 1 and 2, the materials were mixed using a planetary mixer (manufactured by Xinji Corporation, "Defoaming Stir Taro"), and then mixed using a three-roll mill to prepare Example 1 ~9. The sealing compound for liquid crystal display elements of Comparative Examples 1 to 5.
<評價> <evaluation>
對實施例及比較例中所獲得之各液晶顯示元件用密封劑進行以下評價。將結果示於表1、2。 The following evaluation was performed about each sealing compound for liquid crystal display elements obtained in an Example and a comparative example. The results are shown in Tables 1 and 2.
(遮光部硬化性) (Curability of shading part)
首先，準備對厚度0.7mm之康寧玻璃的半面進行鉻蒸鍍而成之基板A、及對前表面進行鉻蒸鍍而成之基板B。其次，利用行星式攪拌裝置使平均粒徑5μm之間隔(spacer)微粒子(積水化學工業公司製造，「Micropearl SI-H050」)1重量份均勻地分散於實施例及比較例中所獲得之各液晶顯示元件用密封劑100重量份，將所獲得之密封劑塗佈於基板A的中央部(鉻蒸鍍部與非蒸鍍部之交界)，貼合基板B後將密封劑充分地壓碎，並自基板A側使用金屬鹵素燈照射30秒鐘之100mW/cm2的紫外線。 First, a substrate A in which chromium is vapor-deposited on a half surface of Corning glass with a thickness of 0.7 mm and a substrate B in which chromium is vapor-deposited on the front surface are prepared. Next, a planetary stirring device was used to uniformly disperse 1 part by weight of spacer particles ("Micropearl SI-H050", manufactured by Sekisui Chemical Industry Co., Ltd.) with an average particle diameter of 5 μm in each liquid crystal obtained in the examples and comparative examples. 100 parts by weight of the sealant for display elements, the obtained sealant was applied to the center part of the substrate A (the boundary between the chromium vapor-deposited part and the non-evaporated part), and the substrate B was laminated and the sealant was sufficiently crushed. A metal halide lamp was used to irradiate ultraviolet rays of 100 mW/cm 2 for 30 seconds from the substrate A side.
然後，使用切割器將基板A及B剝離，對於與紫外線直接照射部之邊緣相距50μm之點(因鉻蒸鍍而被遮光之部分)上之密封劑，利用顯微IR法測定光譜，並利用以下方法求出密封劑中之(甲基)丙烯醯基的轉化率。即，將815~800cm-1之峰面積設為(甲基)丙烯醯基之峰面積，將845~820cm-1之峰面積設為參考峰面積，利用下式算出(甲基)丙烯醯基之轉化率，並將轉化率為90%以上者設為「◎」，將70%以上且未達90%者設為「○」，將50%以上且未達70%者設為「△」，將未達50%者設為「×」，從而對遮光部硬化 性進行評價。 Then, use a cutter to peel off the substrates A and B, and measure the spectrum of the sealant at a point 50 μm away from the edge of the ultraviolet direct irradiation part (the part that is shaded by chromium vapor deposition) by using a micro-IR method. The conversion rate of the (meth)acrylic group in the sealant was determined by the following method. That is, the peak area of 815~800cm -1 is set as the peak area of (meth)acrylic group, and the peak area of 845~820cm -1 is set as the reference peak area, and the (meth)acrylic group is calculated by the following formula Set the conversion rate above 90% as "◎", set the conversion rate above 70% and less than 90% as "○", and set the conversion rate above 50% and less than 70% as "△" , And set the value of less than 50% as "×" to evaluate the curability of the shading part.
(甲基)丙烯醯基之轉化率=(1-(紫外線照射後之(甲基)丙烯醯基之峰面積/紫外線照射後之參考峰面積)/(紫外線照射前之(甲基)丙烯醯基之峰面積/紫外線照射前之參考峰面積))×100 (Meth)acrylic acid conversion rate=(1-((meth)acrylic acid group peak area after ultraviolet irradiation/reference peak area after ultraviolet irradiation)/((meth)acrylic acid group before ultraviolet irradiation) Base peak area/reference peak area before UV irradiation))×100
(液晶顯示元件之顯示性能(低液晶污染性)) (Display performance of liquid crystal display element (low liquid crystal pollution))
利用行星式攪拌裝置使平均粒徑5μm之間隔粒子(積水化學工業公司製造，「Micropearl SI-H050」)1重量份均勻地分散於實施例及比較例中所獲得之各液晶顯示元件用密封劑100重量份，將所獲得之密封劑填充至滴塗用之注射器(武藏工業公司製造，「PSY-10E」)並進行脫泡處理，隨後利用分注器(武藏工業公司製造，「SHOTMASTER300」)將密封劑框狀地塗佈於2片附ITO薄膜之透明電極基板之一者。繼而，將TN液晶(智索公司製造，「JC-5001LA」)之微小滴利用液晶滴加裝置滴加塗佈至密封劑的框內，並利用真空貼合裝置於5Pa之真空下貼合另一透明電極基板而獲得液晶單元。使用金屬鹵素燈對所獲得之單元照射30秒鐘之100mW/cm2的紫外線之後，於120℃加熱1小時而使密封劑硬化，從而獲得液晶顯示元件。 1 part by weight of spacer particles (manufactured by Sekisui Chemical Industry Co., Ltd., "Micropearl SI-H050") with an average particle diameter of 5 μm was uniformly dispersed in each of the sealing compounds for liquid crystal display elements obtained in the Examples and Comparative Examples using a planetary stirring device 100 parts by weight, the obtained sealant is filled into a syringe for drip coating (manufactured by Musashi Kogyo Co., "PSY-10E") and defoamed, followed by a dispenser (manufactured by Musashi Kogyo Co., "SHOTMASTER300") The sealant is applied to one of two transparent electrode substrates with ITO film in a frame shape. Then, small drops of TN liquid crystal (manufactured by Chisso Corporation, "JC-5001LA") were applied to the frame of the sealant using a liquid crystal dropping device, and then bonded under a vacuum of 5 Pa using a vacuum bonding device. A transparent electrode substrate to obtain a liquid crystal cell. After irradiating the obtained cell with ultraviolet rays of 100 mW/cm 2 for 30 seconds using a metal halide lamp, it was heated at 120° C. for 1 hour to harden the sealant, thereby obtaining a liquid crystal display element.
對於所獲得之液晶顯示元件，藉由目測觀察產生於密封部周邊之液晶(尤其是角部)之顯示不均，將未確認到顯示不均之情形設為「◎」，將確認到少量顯示不均之情形設為「○」，將明顯確認到顯示不均之情形設為「△」，將確認到嚴重的顯示不均之情形設為「×」，從而對液晶顯示元件之顯示性能(低液晶污染性)進行評價。 For the obtained liquid crystal display element, the display unevenness of the liquid crystal (especially the corners) generated in the periphery of the sealing part was visually observed, and the case where the display unevenness was not confirmed was set to "◎", and a small amount of display unevenness was confirmed Set the condition of uniformity to "○", set the situation where the display unevenness is clearly confirmed to "△", and set the situation where the serious display unevenness is confirmed to "×", so as to improve the display performance of the liquid crystal display element (low Liquid crystal contamination) was evaluated.
再者，評價為「◎」、「○」之液晶顯示元件為實際使用中完全不存在問題之程度。 Furthermore, the liquid crystal display elements evaluated as "◎" and "○" are to the extent that there is no problem at all in actual use.
[產業上之可利用性] [Industrial availability]
根據本發明，可提供一種遮光部硬化性優異、且可抑制液晶污染之液晶顯示元件用密封劑。又，根據本發明，可提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 According to the present invention, it is possible to provide a sealing compound for a liquid crystal display element which is excellent in curability of a light-shielding portion and can suppress liquid crystal contamination. In addition, according to the present invention, it is possible to provide an upper and lower conduction material and a liquid crystal display element using the sealing compound for liquid crystal display elements.
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| WO2008029893A1 (en) * | 2006-09-07 | 2008-03-13 | Mitsui Chemicals, Inc. | Liquid crystal sealing agent, method for manufacturing liquid crystal display panel using the liquid crystal sealing agent, and liquid crystal display panel |
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| JP5493422B2 (en) * | 2008-05-16 | 2014-05-14 | Ｊｓｒ株式会社 | Curable composition for liquid crystal sealant and liquid crystal display element |
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