TWI707946B - 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
- TWI707946B TWI707946B TW105143879A TW105143879A TWI707946B TW I707946 B TWI707946 B TW I707946B TW 105143879 A TW105143879 A TW 105143879A TW 105143879 A TW105143879 A TW 105143879A TW I707946 B TWI707946 B TW I707946B
- Authority
- TW
- Taiwan
- Prior art keywords
- liquid crystal
- crystal display
- meth
- acrylate
- display elements
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 109
- 239000000463 material Substances 0.000 title claims abstract description 13
- 239000000565 sealant Substances 0.000 title claims description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 238000007789 sealing Methods 0.000 claims abstract description 56
- 229920005989 resin Polymers 0.000 claims abstract description 31
- 239000011347 resin Substances 0.000 claims abstract description 31
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 11
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 91
- 239000004593 Epoxy Substances 0.000 claims description 31
- 239000002245 particle Substances 0.000 claims description 8
- 239000004020 conductor Substances 0.000 claims 1
- 230000035699 permeability Effects 0.000 abstract description 18
- 238000011109 contamination Methods 0.000 abstract description 15
- 239000011248 coating agent Substances 0.000 abstract description 14
- 238000000576 coating method Methods 0.000 abstract description 14
- -1 acrylic compound Chemical class 0.000 description 51
- 239000003822 epoxy resin Substances 0.000 description 44
- 229920000647 polyepoxide Polymers 0.000 description 44
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- 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 19
- 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 17
- 239000000758 substrate Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 13
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000010936 titanium Substances 0.000 description 11
- 229910052719 titanium Inorganic materials 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 229930185605 Bisphenol Natural products 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000011859 microparticle Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000000475 sunscreen effect Effects 0.000 description 4
- 239000000516 sunscreening agent Substances 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
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols 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
- 238000011156 evaluation Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 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
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- XDUZWPPSSHEDFK-VVXQKDJTSA-N C(C(C)(C)C)C([C@H](O)[C@H](O)CO)O Chemical compound C(C(C)(C)C)C([C@H](O)[C@H](O)CO)O XDUZWPPSSHEDFK-VVXQKDJTSA-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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 2
- VZTQQYMRXDUHDO-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)phenyl]propan-2-yl]phenoxy]propyl] prop-2-enoate Chemical compound C=1C=C(OCC(O)COC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCC(O)COC(=O)C=C)C=C1 VZTQQYMRXDUHDO-UHFFFAOYSA-N 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
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- 238000013461 design Methods 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 239000010452 phosphate Substances 0.000 description 2
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
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- 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
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- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-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
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- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
本發明之目的在於提供一種塗佈性、防透濕性及接著性優異，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 liquid crystal display elements which is excellent in coating properties, moisture permeability resistance, and adhesiveness, 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.
本發明之液晶顯示元件用密封劑含有硬化性樹脂與自由基聚合起始劑及/或熱硬化劑，上述硬化性樹脂含有下述式(1)表示之化合物，液晶顯示元件用密封劑中之上述式(1)表示的化合物含量為1重量%以上且未達30重量%。 The sealing compound for liquid crystal display elements of the present invention contains a curable resin and a radical polymerization initiator and/or a thermosetting agent. The curable resin contains a compound represented by the following formula (1). Among the sealing compounds for liquid crystal display elements The content of the compound represented by the above formula (1) is 1% by weight or more and less than 30% by weight.
式(1)中，R1為氫或甲基，m及n分別為0~6。 In formula (1), R 1 is hydrogen or methyl, and m and n are 0-6 respectively.
Description
本發明係關於一種塗佈性、防透濕性及接著性優異，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 that is excellent in coating properties, moisture permeability resistance, and adhesiveness, 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，作為液晶顯示元件之製造方法，就產距時間(tact time)縮短、使用液晶量之最佳化等觀點而言，如專利文獻1、專利文獻2中所揭示，業界採用使用含有硬化性樹脂、光聚合起始劑及熱硬化劑之光熱併用硬化型密封劑之被稱為滴下法之液晶滴下方式。 In recent years, as a method of manufacturing liquid crystal display elements, from the viewpoints of shortening the tact time and optimizing the amount of liquid crystal used, as disclosed in Patent Document 1 and Patent Document 2, the industry has adopted the use of curing It is a liquid crystal dropping method called a dropping method that uses a combination of light and heat with a curable resin, a photopolymerization initiator, and a thermosetting sealant.
關於滴下法，首先，於2片附有電極之透明基板之一片上，藉由分注(dispense)形成長方形密封圖案。繼而，於密封劑未硬化之狀態將液晶之微小滴滴至透明基板之框內整個面，立即與另一透明基板重疊，並對密封部照射紫外線等光而進行暫時硬化。然後，加熱進行正式硬化，而製作液晶顯示元件。藉由在減壓下進行基板之貼合，能夠以極高之效率製造液晶顯示元件，目前該滴下法成為液晶顯示元件製造方法之主流。 Regarding the dropping method, first, a rectangular sealing pattern is formed by dispensing on one of two transparent substrates with electrodes. Then, in the state where the sealant is not hardened, the small droplets of liquid crystal are dropped onto the entire surface of the frame of the transparent substrate, immediately overlap with another transparent substrate, and the sealing part is irradiated with light such as ultraviolet rays to temporarily harden. Then, it is heated for main curing to produce a liquid crystal display element. By bonding the substrates under reduced pressure, the liquid crystal display element can be manufactured with extremely high efficiency. At present, the dropping method has become the mainstream of the liquid crystal display element manufacturing method.
且說，於行動電話、攜帶型遊戲機等各種附液晶面板之移動設備普及之當代，裝置之小型化為最首要謀求之課題。作為裝置小型化之 方法，可列舉液晶顯示部之窄邊緣化，例如業界進行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, with the popularization of various mobile devices with LCD panels, such as mobile phones and portable game consoles, miniaturization of the devices is the most important issue. As a device miniaturization The method can be exemplified by narrowing the edges of the liquid crystal display. For example, in the industry, the position of the sealing part is arranged under the black matrix (hereinafter, also referred to as narrow-edge design).
然而，於窄邊緣設計，由於密封劑係配置於黑矩陣之正下方，故而若實施滴下法，則有於使密封劑光硬化時照射之光被遮蔽，而光未到達密封劑之內部而硬化變得不充分之問題。如此若密封劑之硬化變得不充分，則有如下問題：因未硬化之密封劑成分於液晶中溶出，於液晶中進行由所溶出之密封劑成分引起之硬化反應，故而產生液晶污染。 However, in the narrow-edge design, since the sealant is arranged directly under the black matrix, if the dripping method is implemented, the light irradiated when the sealant is cured by light is blocked, and the light does not reach the inside of the sealant and hardens The problem of becoming insufficient. If the curing of the sealant becomes insufficient in this way, there is a problem that the uncured sealant component is eluted in the liquid crystal, and the curing reaction caused by the eluted sealant component proceeds in the liquid crystal, so liquid crystal contamination occurs.
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
本發明之目的在於提供一種塗佈性、防透濕性及接著性優異，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 liquid crystal display elements which is excellent in coating properties, moisture permeability resistance, and adhesiveness, 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，含有硬化性樹脂與自由基聚合起始劑及/或熱硬化劑，上述硬化性樹脂含有下述式(1)表示之化合物，液晶顯示元件用密封劑中之上述式(1)表示的化合物含量為1重量%以上且未達30重量%。 The present invention is a sealing compound for liquid crystal display elements, which contains a curable resin and a radical polymerization initiator and/or a thermosetting agent. The curable resin contains a compound represented by the following formula (1). The sealing compound for liquid crystal display elements The content of the compound represented by the above formula (1) is 1% by weight or more and less than 30% by weight.
式(1)中，R1為氫或甲基，m及n分別為0~6。 In formula (1), R 1 is hydrogen or methyl, and m and n are 0-6 respectively.
以下對本發明進行詳細說明。 The present invention will be described in detail below.
本發明人對摻合接著性優異，且液晶污染性低之雙酚S型環氧樹脂作為硬化性樹脂進行研究。然而，於使用雙酚S型環氧樹脂之情形時，亦有抑制液晶污染之效果不充分，或所獲得之液晶顯示元件用密封劑成為塗佈性或防透濕性差者之問題。 The present inventors studied bisphenol S-type epoxy resin, which is excellent in blending adhesion and low in liquid crystal contamination, as a curable resin. However, when the bisphenol S-type epoxy resin is used, the effect of suppressing liquid crystal contamination is insufficient, or the obtained sealing compound for liquid crystal display elements has poor coating properties or moisture permeability.
因此，本發明人等發現，藉由摻合特定量之具有雙酚S型結構之特定化合物，可獲得塗佈性、防透濕性及接著性優異，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。 Therefore, the present inventors found that by blending a specific amount of a specific compound having a bisphenol S-type structure, it is possible to obtain a liquid crystal display device with excellent coating properties, moisture permeability resistance, and adhesion, and can suppress liquid crystal contamination. Sealant, thus completing the present 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上述式(1)表示之化合物。藉由含有上述式(1)表示之化合物，本發明之液晶顯示元件用密封劑成為接著性及抑制液晶污染之效果優異者。 The curable resin contains the compound represented by the formula (1). By containing the compound represented by the above formula (1), the sealing compound for liquid crystal display elements of the present invention is excellent in adhesiveness and the effect of suppressing liquid crystal contamination.
上述式(1)中，m及n分別為0~6。上述m及n較佳分別為1~6，更佳分別為1~3。 In the above formula (1), m and n are respectively 0-6. The above m and n are preferably 1 to 6, and more preferably 1 to 3, respectively.
再者，上述式(1)及下述式(2)之m及n之值為平均值。又，所謂m或n為0之情形係指附有m或n之環氧乙烷結構部分成為鍵結鍵。 Furthermore, the values of m and n in the above formula (1) and the following formula (2) are average values. In addition, the case where m or n is 0 means that the ethylene oxide moiety to which m or n is attached becomes a bonding bond.
作為製造上述式(1)表示之化合物的方法，例如可列舉：藉由使雙酚S或環氧乙烷加成雙酚S與表氯醇進行反應，而製造下述式(2) 表示之化合物，並使所獲得之式(2)表示之化合物的一環氧基與(甲基)丙烯酸進行反應之方法等。 As a method for producing the compound represented by the above formula (1), for example, the following formula (2) is produced by reacting bisphenol S or ethylene oxide addition bisphenol S with epichlorohydrin The compound represented by the formula (2) is obtained, and a method of reacting (meth)acrylic acid with an epoxy group of the compound represented by formula (2).
再者，於本說明書，上述所謂「(甲基)丙烯酸」係指丙烯酸或甲基丙烯酸。 In addition, in this specification, the aforementioned "(meth)acrylic acid" means acrylic acid or methacrylic acid.
式(2)中，m及n分別為0~6。 In formula (2), m and n are 0-6 respectively.
本發明之液晶顯示元件用密封劑中之上述式(1)表示之化合物含量為1重量%以上且未達30重量%。若上述式(1)表示之化合物含量未達1重量%，則所獲得之液晶顯示元件用密封劑容易成為接著性差者。若上述式(1)表示之化合物含量為30重量%以上，則所獲得之顯示元件用密封劑成為塗佈性或防透濕性差者。上述式(1)表示之化合物含量較佳之下限為5重量%，較佳之上限為25重量%，更佳之下限為10重量%，更佳之上限為20重量%，進而較佳之上限為15重量%。 The content of the compound represented by the formula (1) in the sealing compound for liquid crystal display elements of the present invention is 1% by weight or more and less than 30% by weight. If the content of the compound represented by the above formula (1) is less than 1% by weight, the obtained sealing compound for liquid crystal display elements is likely to have poor adhesiveness. If the content of the compound represented by the above formula (1) is 30% by weight or more, the obtained sealant for display elements will have poor coatability or moisture permeability. The lower limit of the content of the compound represented by the above formula (1) is preferably 5% by weight, the upper limit is preferably 25% by weight, the lower limit is more preferably 10% by weight, the upper limit is more preferably 20% by weight, and the upper limit is more preferably 15% by weight.
上述硬化性樹脂較佳除含有上述式(1)表示之化合物以外，還含有其他硬化性樹脂。 The curable resin preferably contains other curable resins in addition to the compound represented by the formula (1).
作為上述其他硬化性樹脂，例如可列舉：上述式(1)表示之化合物以外之(甲基)丙烯酸化合物或環氧化合物等。其中，作為上述(甲基)丙烯酸化合物，較佳含有下述環氧(甲基)丙烯酸酯，更佳含有間苯二酚型環氧(甲基)丙烯酸酯。 As said other curable resin, for example, a (meth)acrylic compound or epoxy compound other than the compound represented by the above formula (1) may be mentioned. Among them, the (meth)acrylic compound preferably contains the following epoxy (meth)acrylate, and more preferably contains a resorcinol type epoxy (meth)acrylate.
再者，於本說明書，上述所謂「(甲基)丙烯酸酯」係指丙烯酸酯或甲基丙烯酸酯，所謂「環氧(甲基)丙烯酸酯」表示使環氧化合物中之所有環氧基與(甲基)丙烯酸進行反應而成之化合物。 Furthermore, in this specification, the above-mentioned "(meth)acrylate" refers to acrylate or methacrylate, and the so-called "epoxy (meth)acrylate" refers to the combination of all epoxy groups in the epoxy compound (Meth)Acrylic acid reacts with a compound.
作為上述其他硬化性樹脂之(甲基)丙烯酸化合物，例如可列舉：藉由使(甲基)丙烯酸與環氧化合物進行反應而獲得之環氧(甲基)丙烯酸酯、藉由使(甲基)丙烯酸與具有羥基之化合物進行反應而獲得之(甲基)丙烯酸酯化合物、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而獲得之(甲基)丙烯酸胺基甲酸酯等，如上所述，較佳為環氧(甲基)丙烯酸酯。又，上述(甲基)丙烯酸化合物就反應性高之方面而言，較佳為分子中具有2個以上(甲基)丙烯醯基者。 Examples of the (meth)acrylic compound of the other curable resin include: epoxy (meth)acrylate obtained by reacting (meth)acrylic acid with an epoxy compound; ) A (meth)acrylate compound obtained by reacting acrylic acid with a compound having a hydroxyl group, and a (meth)acrylic urethane compound obtained by reacting an isocyanate compound with a (meth)acrylic acid derivative having a hydroxyl group As described above, the ester and the like are preferably epoxy (meth)acrylate. Furthermore, the above-mentioned (meth)acrylic compound is preferably one having two or more (meth)acrylic groups in the molecule in terms of high reactivity.
作為上述環氧(甲基)丙烯酸酯，例如可列舉藉由使環氧化合物與(甲基)丙烯酸根據常法於鹼性觸媒之存在下進行反應而獲得者等。 As said epoxy (meth)acrylate, the thing obtained by making an epoxy compound and (meth)acrylic acid react in the presence of a basic catalyst according to a common method, etc. are mentioned, for example.
作為成為用於合成上述環氧(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、2,2'-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、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、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、環氧丙酯化合物等。其中，較佳為間苯二酚型環氧樹脂。 As the epoxy compound used as a raw material for synthesizing the above-mentioned epoxy (meth)acrylate, for example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol E type epoxy resin, bisphenol E Phenol S type epoxy resin, 2,2'-diallyl bisphenol A type epoxy resin, hydrogenated bisphenol type epoxy resin, propylene oxide addition bisphenol A type epoxy resin, resorcinol type Epoxy resin, biphenyl type epoxy resin, thioether type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol novolac type epoxy resin , O-cresol novolak type epoxy resin, dicyclopentadiene novolak type epoxy resin, biphenol novolak type epoxy resin, naphthol novolak type epoxy resin, glycidyl amine type epoxy resin, alkane Base polyol type epoxy resin, rubber modified type epoxy resin, glycidyl ester compound, etc. Among them, resorcinol type epoxy resins are preferred.
作為上述雙酚A型環氧樹脂中之市售者，例如可列舉：jER828EL、jER1004(均為三菱化學公司製造)、Epiclon 850CRP(迪愛生公司製造)等。 Examples of commercially available bisphenol A-type epoxy resins include jER828EL, jER1004 (all manufactured by Mitsubishi Chemical Corporation), Epiclon 850CRP (manufactured by Di Aisheng), and the like.
作為上述雙酚F型環氧樹脂中之市售者，例如可列舉jER806、jER4004(均為三菱化學公司製造)等。 Examples of commercially available bisphenol F-type epoxy resins include jER806 and jER4004 (all manufactured by Mitsubishi Chemical Corporation).
作為上述雙酚E型環氧樹脂中之市售者，例如可列舉R710(Printec公司製造)等。 Examples of commercially available bisphenol E epoxy resins include R710 (manufactured by Printec Corporation).
作為上述雙酚S型環氧樹脂中之市售者，例如可列舉Epiclon EXA1514(迪愛生公司製造)等。 As a commercially available one among the above-mentioned bisphenol S-type epoxy resins, for example, Epiclon EXA1514 (manufactured by D&E Corporation) and the like can be cited.
作為上述2,2'-二烯丙基雙酚A型環氧樹脂中之市售者，例如可列舉RE-810NM(日本化藥公司製造)等。 As a commercially available one among the above-mentioned 2,2'-diallylbisphenol A epoxy resins, for example, RE-810NM (manufactured by Nippon Kayaku Co., Ltd.) and the like can be cited.
作為上述氫化雙酚型環氧樹脂中之市售者，例如可列舉Epiclon EXA7015(迪愛生公司製造)等。 As a commercially available one among the above-mentioned hydrogenated bisphenol-type epoxy resins, Epiclon EXA7015 (manufactured by Dyson Co., Ltd.) etc. are mentioned, for example.
作為上述環氧丙烷加成雙酚A型環氧樹脂中之市售者，例如可列舉EP-4000S(艾迪科公司製造)等。 As a commercially available one among the above-mentioned propylene oxide-added bisphenol A epoxy resins, for example, EP-4000S (manufactured by Adic Co., Ltd.) can be cited.
作為上述間苯二酚型環氧樹脂中之市售者，例如可列舉EX-201(長瀨化成公司製造)等。 As a commercially available one among the above-mentioned resorcinol-type epoxy resins, EX-201 (manufactured by Nagase Kasei Co., Ltd.) etc. are mentioned, for example.
作為上述聯苯型環氧樹脂中之市售者，例如可列舉jER YX-4000H(三菱化學公司製造)等。 As a commercial item among the said biphenyl type epoxy resin, jER YX-4000H (made by Mitsubishi Chemical Corporation) etc. are mentioned, for example.
作為上述硫醚型環氧樹脂中之市售者，例如可列舉YSLV-50TE(新日鐵住金化學公司製造)等。 Examples of commercially available sulfide epoxy resins include YSLV-50TE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
作為上述二苯醚型環氧樹脂中之市售者，例如可列舉YSLV-80DE(新 日鐵住金化學公司製造)等。 As a commercially available one among the above-mentioned diphenyl ether epoxy resins, for example, YSLV-80DE (new Nippon Steel & Sumikin Chemical Co.), etc.
作為上述二環戊二烯型環氧樹脂中之市售者，例如可列舉EP-4088S(艾迪科公司製造)等。 As a commercially available one among the above-mentioned dicyclopentadiene-type epoxy resins, EP-4088S (manufactured by Adic Co., Ltd.) etc. are mentioned, for example.
作為上述萘型環氧樹脂中之市售者，例如可列舉Epiclon HP4032、Epiclon EXA-4700(均為迪愛生公司製造)等。 As a commercially available one among the above-mentioned naphthalene type epoxy resins, Epiclon HP4032, Epiclon EXA-4700 (both are manufactured by D&E Corporation), etc. are mentioned, for example.
作為上述酚系酚醛清漆型環氧樹脂中之市售者，例如可列舉Epiclon N-770(迪愛生公司製造)等。 Examples of commercially available phenolic novolac epoxy resins include Epiclon N-770 (manufactured by Di Aisheng).
作為上述鄰甲酚酚醛清漆型環氧樹脂中之市售者，例如可列舉Epiclon N-670-EXP-S(迪愛生公司製造)等。 As a commercially available one among the o-cresol novolak-type epoxy resins mentioned above, for example, Epiclon N-670-EXP-S (manufactured by Di Aisheng) etc. is mentioned.
作為上述二環戊二烯酚醛清漆型環氧樹脂中之市售者，例如可列舉Epiclon HP7200(迪愛生公司製造)等。 As a commercially available one among the above-mentioned dicyclopentadiene novolak type epoxy resins, for example, Epiclon HP7200 (manufactured by Di Aison Co., Ltd.) and the like can be cited.
作為上述聯苯酚醛清漆型環氧樹脂中之市售者，例如可列舉NC-3000P(日本化藥公司製造)等。 Examples of commercially available biphenol novolak type epoxy resins include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.).
作為上述萘酚酚醛清漆型環氧樹脂中之市售者，例如可列舉ESN-165S(新日鐵住金化學公司製造)等。 As a commercially available one among the above-mentioned naphthol novolac type epoxy resins, for example, ESN-165S (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) and the like can be cited.
作為上述縮水甘油胺型環氧樹脂中之市售者，例如可列舉：jER630(三菱化學公司製造)、Epiclon 430(迪愛生公司製造)、TETRAD-X(三菱瓦斯化學公司製造)等。 Examples of commercially available glycidylamine-type epoxy resins include jER630 (manufactured by Mitsubishi Chemical Corporation), Epiclon 430 (manufactured by Di Aisheng), TETRAD-X (manufactured by Mitsubishi Gas Chemical Corporation), and the like.
作為上述烷基多元醇型環氧樹脂中之市售者，例如可列舉：ZX-1542(新日鐵住金化學公司製造)、Epiclon 726(迪愛生公司製造)、Epolight 80MFA(共榮社化學公司製造)、DENACOL EX-611(長瀨化成公司製造)等。 As commercially available among the above-mentioned alkyl polyol type epoxy resins, for example, ZX-1542 (manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd.), Epiclon 726 (manufactured by Di Aisheng), Epolight 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.) Manufacturing), DENACOL EX-611 (manufactured by Nagase Chemical Co., Ltd.), etc.
作為上述橡膠改質型環氧樹脂中之市售者，例如可列舉：YR-450、YR-207(均為新日鐵住金化學公司製造)、Epolead PB(大賽璐公司製造)等。 Examples of commercially available ones among the above-mentioned rubber-modified epoxy resins include YR-450, YR-207 (all manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epolead PB (manufactured by Daicel Corporation), and the like.
作為上述環氧丙酯化合物中之市售者，例如可列舉DENACOL EX-147(長瀨化成公司製造)等。 As a commercial item among the said glycidyl ester compounds, DENACOL EX-147 (manufactured by Nagase Kasei Co., Ltd.) etc. are mentioned, for example.
作為上述環氧化合物中之其他市售者，例如可列舉：YDC-1312、YSLV-80XY、YSLV-90CR(均為新日鐵住金化學公司製造)、XAC4151(旭化成公司製造)、jER1031、jER1032(均為三菱化學公司製造)、EXA-7120(迪愛生公司製造)、TEPIC(日產化學公司製造)等。 As other commercially available ones of the above epoxy compounds, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Co., Ltd.), jER1031, jER1032 ( All products are manufactured by Mitsubishi Chemical Corporation), EXA-7120 (manufactured by D&E Corporation), TEPIC (manufactured by Nissan Chemical Corporation), etc.
作為上述環氧(甲基)丙烯酸酯中之市售者，例如可列舉：EBECRYL 860、EBECRYL 3200、EBECRYL 3201、EBECRYL 3412、EBECRYL 3600、EBECRYL 3700、EBECRYL 3701、EBECRYL 3702、EBECRYL 3703、EBECRYL 3708、EBECRYL 3800、EBECRYL 6040、EBECRYL RDX63182(均為大賽璐湛新公司製造)、EA-1010、EA-1020、EA-5323、EA-5520、EA-CHD、EMA-1020(均為新中村化學工業公司製造)、Epoxy Ester M-600A、Epoxy Ester 40EM、Epoxy Ester 70PA、Epoxy Ester 200PA、Epoxy Ester 80MFA、Epoxy Ester 3002M、Epoxy Ester 3002A、Epoxy Ester 1600A、Epoxy Ester 3000M、Epoxy Ester 3000A、Epoxy Ester 200EA、Epoxy Ester 400EA(均為共榮社化學公司製造)、DENACOL Acrylate DA-141、DENACOL Acrylate DA-314、DENACOL Acrylate DA-911(均為長瀨化成公司製造)等。 Examples of commercially available epoxy (meth)acrylates include: EBECRYL 860, EBECRYL 3200, EBECRYL 3201, EBECRYL 3412, EBECRYL 3600, EBECRYL 3700, EBECRYL 3701, EBECRYL 3702, EBECRYL 3703, EBECRYL 3708, EBECRYL 3800, EBECRYL 6040, EBECRYL RDX63182 (all manufactured by Daicel Zhanxin), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (all of Shin Nakamura Chemical Industry Co., Ltd.) Manufacturing), Epoxy Ester M-600A, Epoxy Ester 40EM, Epoxy Ester 70PA, Epoxy Ester 200PA, Epoxy Ester 80MFA, Epoxy Ester 3002M, Epoxy Ester 3002A, Epoxy Ester 1600A, Epoxy Ester 3000M, Epoxy Ester 3000A, Epoxy Ester 200EA, Epoxy Ester 200EA Ester 400EA (all manufactured by Kyoeisha Chemical Co., Ltd.), DENACOL Acrylate DA-141, DENACOL Acrylate DA-314, DENACOL Acrylate DA-911 (all manufactured by Nagase Chemical Co., Ltd.), etc.
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)丙烯酸雙環戊烯酯、(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、甲氧基聚乙二醇(甲基)丙烯酸酯、苯氧基二乙二醇(甲基)丙烯酸酯、苯氧基聚乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸四氫糠酯、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)丙烯酸二甲基胺基乙酯、(甲基)丙烯酸二乙基胺基乙酯、琥珀酸2-(甲基)丙烯醯氧基乙酯、六氫酞酸2-(甲基)丙烯醯氧基乙酯、鄰苯二甲酸2-(甲基)丙烯醯氧基乙酯-2-羥基丙酯、磷酸2-(甲基)丙烯醯氧基乙酯、縮水甘油(甲基)丙烯酸酯等。 Examples of monofunctional ones in the above-mentioned (meth)acrylate compounds include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, and n-butyl (meth)acrylate. Esters, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, 2-(meth)acrylate Ethylhexyl, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, ( Isomyristyl (meth)acrylate, stearyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate , 4-hydroxybutyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentenyl (meth)acrylate, benzyl (meth)acrylate, (meth)acrylate Base) 2-methoxyethyl acrylate, 2-ethoxyethyl (meth)acrylate, 2-butoxyethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, Methoxyethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate Base) acrylate, tetrahydrofurfuryl (meth)acrylate, ethyl carbitol (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, (meth)acrylic acid-2 ,2,3,3-Tetrafluoropropyl, (meth)acrylate 1H,1H,5H-octafluoropentyl ester, imine (meth)acrylate, dimethylaminoethyl (meth)acrylate , Diethylaminoethyl (meth)acrylate, 2-(meth)acryloxyethyl succinate, 2-(meth)acryloxyethyl hexahydrophthalate, phthalic acid 2-(meth)acryloxyethyl-2-hydroxypropyl, 2-(meth)acryloxyethyl phosphate, glycidyl (meth)acrylate, etc.
又，作為上述(甲基)丙烯酸酯化合物中之二官能者，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、聚乙二醇二(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、聚丙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸 酯、環氧乙烷加成雙酚A二(甲基)丙烯酸酯、環氧丙烷加成雙酚A二(甲基)丙烯酸酯、環氧乙烷加成雙酚F二(甲基)丙烯酸酯、二(甲基)丙烯酸二羥甲基二環戊二烯酯、環氧乙烷改質異三聚氰酸二(甲基)丙烯酸酯、(甲基)丙烯酸2-羥基-3-(甲基)丙烯醯氧基丙酯、碳酸酯二醇二(甲基)丙烯酸酯、聚醚二醇二(甲基)丙烯酸酯、聚酯二醇二(甲基)丙烯酸酯、聚己內酯二醇二(甲基)丙烯酸酯、聚丁二烯二醇二(甲基)丙烯酸酯等。 In addition, examples of the bifunctional of 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, polyethylene glycol di(meth)acrylate, 2-n-butyl-2 -Ethyl-1,3-propanediol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, neopentyl diacrylate Alcohol bis(meth)acrylic acid Ester, ethylene oxide addition of bisphenol A di(meth)acrylate, propylene oxide addition of bisphenol A di(meth)acrylate, ethylene oxide addition of bisphenol F di(meth)acrylic acid Ester, dimethylol dicyclopentadiene di(meth)acrylate, ethylene oxide modified isocyanuric acid di(meth)acrylate, (meth)acrylic acid 2-hydroxy-3-( Meth) acryloxy propyl ester, carbonate glycol di(meth)acrylate, polyether glycol di(meth)acrylate, polyester glycol di(meth)acrylate, polycaprolactone Glycol di(meth)acrylate, polybutadienediol di(meth)acrylate, etc.
又，作為上述(甲基)丙烯酸酯化合物中之三官能以上者，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、環氧丙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成異三聚氰酸三(甲基)丙烯酸酯、三(甲基)丙烯酸甘油酯、環氧丙烷加成三(甲基)丙烯酸甘油酯、新戊四醇三(甲基)丙烯酸酯、磷酸三(甲基)丙烯醯氧基乙酯、二-三羥甲基丙烷四(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯等。 In addition, examples of the above-mentioned (meth)acrylate compounds having three or more functions include trimethylolpropane tri(meth)acrylate, ethylene oxide addition trimethylolpropane tri(methyl) )Acrylate, propylene oxide addition trimethylolpropane tri(meth)acrylate, ethylene oxide addition isocyanuric acid tri(meth)acrylate, tri(meth)glycerol acrylate, Addition of propylene oxide to glycerol tri(meth)acrylate, neopentylerythritol tri(meth)acrylate, tri(meth)acryloyloxyethyl phosphate, di-trimethylolpropane tetra(methyl) ) Acrylate, neopentylerythritol tetra(meth)acrylate, dineopentaerythritol penta(meth)acrylate, dineopentaerythritol hexa(meth)acrylate, etc.
作為上述(甲基)丙烯酸胺基甲酸酯，例如可藉由相對於具有2個異氰酸酯基之異氰酸酯化合物1當量，使具有羥基之(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 above-mentioned (meth)acrylate urethane, for example, 2 equivalents of the (meth)acrylic acid derivative having a hydroxyl group can be made to the amount of the tin-based catalyst by 1 equivalent of the isocyanate compound having 2 isocyanate groups. It is obtained by reacting in the presence of the 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、二苯基甲烷-4,4'-二異氰酸酯(MDI)、氫化MDI、聚合MDI、1,5-萘二異氰酸酯、降莰烷二異氰酸酯、聯甲苯胺二異氰酸酯、苯二甲基二異氰酸酯(XDI)、氫化XDI、離胺酸二異氰酸酯、三苯基甲烷三異氰酸酯、三(異氰 酸酯基苯基)硫代磷酸酯、四甲基二甲苯二異氰酸酯、1,6,11-十一烷三異氰酸酯等。 As the isocyanate compound used as the raw material of the (meth)acrylate urethane, for example, isophorone diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, hexamethylene Diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, biphenylmethane Toluidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris(isocyanate) Ester phenyl) phosphorothioate, tetramethylxylene diisocyanate, 1,6,11-undecane triisocyanate, etc.
又，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，例如亦可使用藉由乙二醇、丙二醇、甘油、山梨糖醇、三羥甲基丙烷、碳酸酯二醇、聚醚二醇、聚酯二醇、聚己內酯二醇等多元醇與過量之異氰酸酯化合物之反應而獲得之經鏈延長之異氰酸酯化合物。 In addition, as the isocyanate compound used as the raw material of the (meth)acrylate urethane, for example, ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, A chain-extended isocyanate compound obtained by the reaction of polyether diol, polyester diol, polycaprolactone diol and other polyols with excess isocyanate compounds.
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、聚乙二醇等二元醇之單(甲基)丙烯酸酯、或三羥甲基乙烷、三羥甲基丙烷、甘油等三元醇之單(甲基)丙烯酸酯或二(甲基)丙烯酸酯、或者雙酚A型環氧丙烯酸酯等環氧(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 ,3-butanediol, 1,4-butanediol, polyethylene glycol and other dihydric alcohol mono(meth)acrylate, or trimethylolethane, trimethylolpropane, glycerin and other ternary Mono(meth)acrylate or di(meth)acrylate of alcohol, or epoxy (meth)acrylate such as bisphenol A epoxy acrylate, etc.
作為上述(甲基)丙烯酸胺基甲酸酯中之市售者，例如可列舉：M-1100、M-1200、M-1210、M-1600(均為東亞合成公司製造)、EBECRYL 210、EBECRYL 220、EBECRYL 230、EBECRYL 270、EBECRYL 1290、EBECRYL 2220、EBECRYL 4827、EBECRYL 4842、EBECRYL 4858、EBECRYL 5129、EBECRYL 6700、EBECRYL 8402、EBECRYL 8803、EBECRYL 8804、EBECRYL 8807、EBECRYL 9260(均為大賽璐湛新公司製造)、Artresin UN-330、Artresin SH-500B、Artresin UN-1200TPK、Artresin UN-1255、Artresin UN-3320HB、Artresin UN-7100、Artresin UN-9000A、Artresin UN -9000H(均為根上工業公司製造)、U-2HA、U-2PHA、U-3HA、U-4HA、 U-6H、U-6HA、U-6LPA、U-10H、U-15HA、U-108、U-108A、U-122A、U-122P、U-324A、U-340A、U-340P、U-1084A、U-2061BA、UA-340P、UA-4000、UA-4100、UA-4200、UA-4400、UA-5201P、UA-7100、UA-7200、UA-W2A(均為新中村化學工業公司製造)、AH-600、AI-600、AT-600、UA-101I、UA-101T、UA-306H、UA-306I、UA-306T(均為共榮社化學公司製造)等。 Examples of commercially available (meth)acrylate urethanes include: M-1100, M-1200, M-1210, M-1600 (all manufactured by Toagosei Co., Ltd.), EBECRYL 210, EBECRYL 220, EBECRYL 230, EBECRYL 270, EBECRYL 1290, EBECRYL 2220, EBECRYL 4827, EBECRYL 4842, EBECRYL 4858, EBECRYL 5129, EBECRYL 6700, EBECRYL 8402, EBECRYL 8803, EBECRYL 8804, all EBECRYL 8260, EBECRYL 9807 Manufactured by the company), Artresin UN-330, Artresin SH-500B, Artresin UN-1200TPK, Artresin UN-1255, Artresin UN-3320HB, Artresin UN-7100, Artresin UN-9000A, Artresin UN-9000H (all manufactured by Nejo Kogyo) ), U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6HA, U-6LPA, U-10H, U-15HA, U-108, U-108A, U-122A, U-122P, U-324A, U-340A, U-340P, U- 1084A, U-2061BA, UA-340P, UA-4000, UA-4100, UA-4200, UA-4400, UA-5201P, UA-7100, UA-7200, UA-W2A (all manufactured by Shinnakamura Chemical Industry Co., Ltd. ), AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (all manufactured by Kyoeisha Chemical Co., Ltd.), etc.
作為上述其他硬化性樹脂之環氧化合物，例如可列舉：成為用於合成上述環氧(甲基)丙烯酸酯之原料的環氧化合物，或式(1)表示之化合物以外之部分(甲基)丙烯酸改質環氧樹脂等。 As the epoxy compound of the other curable resin, for example, an epoxy compound used as a raw material for synthesizing the epoxy (meth)acrylate, or a part (methyl) other than the compound represented by formula (1) Acrylic modified epoxy resin, etc.
再者，於本說明書，上述所謂部分(甲基)丙烯酸改質環氧樹脂係指1分子中分別具有1個以上之環氧基與(甲基)丙烯醯基之化合物，例如可藉由使2個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 partially (meth)acrylic modified epoxy resin refers to a compound having at least one epoxy group and (meth)acryloyl group in one molecule, for example, Part of epoxy groups of two or more epoxy compounds is obtained by reacting (meth)acrylic acid.
上述部分(甲基)丙烯酸改質環氧樹脂之中，作為市售者，例如可列舉UVACURE1561(大賽璐湛新公司製造)等。 Among the above-mentioned partially (meth)acrylic modified epoxy resins, as a commercially available one, for example, UVACURE 1561 (manufactured by Daicel Zhanxin Co., Ltd.) can be cited.
於含有上述其他硬化性樹脂之情形時，硬化性樹脂全部100重量份中之上述式(1)表示之化合物含量較佳之下限為5重量份，較佳之上限為25重量份。藉由上述式(1)表示之化合物含量為該範圍，所獲得之液晶顯示元件用密封劑成為塗佈性、接著性、防透濕性及抑制液晶污染之效果更優異者。上述式(1)表示之化合物含量更佳之下限為10重量份，更佳之上限為20重量份。 When the above-mentioned other curable resin is contained, the lower limit of the content of the compound represented by the above formula (1) in 100 parts by weight of the curable resin is preferably 5 parts by weight and the upper limit is preferably 25 parts by weight. When the content of the compound represented by the above formula (1) is in this range, the obtained sealing compound for liquid crystal display elements is more excellent in coatability, adhesiveness, moisture permeability, and effect of suppressing liquid crystal contamination. The lower limit of the content of the compound represented by the above formula (1) is more preferably 10 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較佳為將硬化性樹脂中之(甲基)丙烯醯基與環氧基之含有比率以莫耳比設為50：50~95：5。 In the sealing compound for liquid crystal display elements of the present invention, it is preferable that the content ratio of the (meth)acrylic group and the epoxy group in the curable resin is 50:50 to 95:5 in molar ratio.
本發明之液晶顯示元件用密封劑含有自由基聚合起始劑及/或熱硬化劑。 The sealing compound for liquid crystal display elements of this invention contains a radical polymerization initiator and/or a thermosetting agent.
作為上述自由基聚合起始劑，可列舉藉由光照射產生自由基之光自由基聚合起始劑、或藉由加熱產生自由基之熱自由基聚合起始劑等。 Examples of the radical polymerization initiator include photoradical polymerization initiators that generate radicals by light irradiation, thermal radical polymerization initiators that generate radicals by heating, and the like.
作為上述光自由基聚合起始劑，例如可列舉：二苯甲酮系化合物、苯乙酮系化合物、醯基氧化膦系化合物、二茂鈦系化合物、肟酯系化合物、安息香醚系化合物、9-氧硫
作為上述光自由基聚合起始劑中之市售者，例如可列舉：IRGACURE 184、IRGACURE 369、IRGACURE 379、IRGACURE 651、IRGACURE 819、IRGACURE 907、IRGACURE 2959、IRGACURE OXE01、Lucirin TPO(均為巴斯夫公司製造)、NCI-930(艾迪科公司製造)、SPEEDCURE EMK(日本Siber Hegner公司製造)、安息香甲醚、安息香乙醚、安息香異丙醚(均為東京化成工業公司製造)等。 Examples of commercially available photo radical polymerization initiators include: IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE OXE01, Lucirin TPO (all of which are BASF Manufacturing), NCI-930 (manufactured by Adike), SPEEDCURE EMK (manufactured by Siber Hegner, Japan), benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (all manufactured by Tokyo Chemical Industry Co., Ltd.), etc.
作為上述熱自由基聚合起始劑，例如可列舉由偶氮化合物、有機過氧化物等所構成者。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係指具有偶氮基，且藉由熱而生成可使(甲基)丙烯醯基硬化之自由基，且數量平均分子量為300以上之化合物。 Furthermore, in this specification, the so-called polymer azo compound refers to a compound having an azo group and generating a radical that can harden the (meth)acryloyl group by heat, and having a number average molecular weight of 300 or more .
上述高分子偶氮起始劑之數量平均分子量較佳之下限為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，且與硬化性樹脂容易混合。上述高分子偶氮 起始劑之數量平均分子量更佳之下限為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 lower limit of the number average molecular weight of the polymer azo initiator is preferably 1,000, and the upper limit is preferably 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. Azo The lower limit of the number average molecular weight of the 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藉由凝膠滲透層析法(GPC)進行測定，並藉由聚苯乙烯換算所求出之值。作為藉由GPC測定由聚苯乙烯換算所獲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 above-mentioned number average molecular weight is a value determined by gel permeation chromatography (GPC) and calculated by polystyrene conversion. As a column for measuring the number average molecular weight obtained by conversion of polystyrene by GPC, for example, Shodex LF-804 (manufactured by Showa Denko Corporation) and the like 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鍵結有多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鍵結有多個聚環氧烷等單元之結構之高分子偶氮起始劑，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)與聚烷二醇之縮聚物、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。 As the polymer azo initiator having a structure in which a plurality of units such as polyalkylene oxide are bonded via an azo group, one having a polyethylene oxide structure is preferred. As such a polymer azo initiator, for example, a condensation polymer of 4,4'-azobis(4-cyanovaleric acid) and polyalkylene glycol, or 4,4'-azobis(4 -Cyanovaleric acid) and polydimethylsiloxane having a terminal amine group. Specifically, for example, VPE-0201, VPE-0401, VPE-0601, VPS-0501, VPS- 1001 (all manufactured by Wako Pure Chemical Industries, Ltd.), etc.
又，作為不為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。 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、氫過氧化物、過氧化二烷基、過氧酯、過氧化二醯基、過氧化二碳酸酯等。 As said organic peroxide, for example, ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacyl peroxide, peroxydicarbonate, etc. are mentioned.
上述自由基聚合起始劑之含量，相對於硬化性樹脂100重量份，較佳之下限為0.01重量份，較佳之上限為10重量份。藉由上述自由基聚合起始劑之含量為該範圍，獲得之液晶顯示元件用密封劑成為抑制液晶污染，並且保存穩定性或硬化性更優異者。上述自由基聚合起始劑之含量 更佳之下限為0.1重量份，更佳之上限為5重量份。 The content of the above-mentioned radical polymerization initiator is preferably 0.01 parts by weight in the lower limit and 10 parts by weight in the upper limit with respect to 100 parts by weight of the curable resin. When the content of the radical polymerization initiator is within 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 content of the above radical polymerization initiator A more preferable lower limit is 0.1 parts by weight, and a more preferable upper limit is 5 parts by weight.
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，可適宜地使用有機酸醯肼。 As said thermosetting agent, organic acid hydrazine, imidazole derivatives, amine compounds, polyphenol compounds, acid anhydrides, etc. are mentioned, for example. Among them, organic acid hydrazine can be suitably used.
作為上述有機酸醯肼，例如可列舉：癸二酸二醯肼、間苯二甲酸二醯肼、己二酸二醯肼、丙二酸二醯肼等。 As said organic acid hydrazine, dihydrazine sebacate, dihydrazine isophthalate, dihydrazine adipic acid, dihydrazine malonate, etc. are mentioned, for example.
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，較佳之下限為1重量份，較佳之上限為50重量份。藉由上述熱硬化劑含量為該範圍，可製成不使所獲得之液晶顯示元件用密封劑之塗佈性等惡化，且熱硬化性更優異者。上述熱硬化劑含量更佳之上限為30重量份。 With respect to 100 parts by weight of the curable resin, the lower limit of the content of the thermosetting agent is preferably 1 part by weight, and the upper limit is preferably 50 parts by weight. When the content of the thermosetting agent is in this range, it is possible to obtain one that does not deteriorate the coating properties of the obtained sealing compound for liquid crystal display elements and has more excellent thermosetting properties. The upper limit of the content of the thermal hardener is more preferably 30 parts by weight.
本發明之液晶顯示元件用密封劑為了提高黏度、改善基於應力分散效果之接著性、改善線膨脹率、提高硬化物之防透濕性等，較佳含有填充劑。 The sealing compound for liquid crystal display elements of the present invention preferably contains a filler in order to increase the viscosity, improve the adhesiveness based on the stress dispersion effect, improve the linear expansion rate, and increase the moisture permeability of the cured product.
作為上述填充劑，例如可列舉：二氧化矽、滑石、玻璃珠、石棉、石膏、矽藻土、膨潤石、膨潤土、蒙脫石、絹雲母、活性白土、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、乙烯基聚合物微粒子、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, Magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate and other inorganic fillers; or polyester microparticles, polyamine based Organic fillers such as formate microparticles, vinyl polymer microparticles, and acrylic polymer microparticles.
本發明之液晶顯示元件用密封劑中之上述填充劑含量較佳 之下限為10重量%，較佳之上限為70重量%。藉由上述填充劑之含量為該範圍，成為不使塗佈性等惡化，且接著性之改善等效果更優異者。上述填充劑含量更佳之下限為20重量%，更佳之上限為60重量%。 The content of the filler in the sealing compound for liquid crystal display elements of the present invention is better The lower limit is 10% by weight, and the preferred upper limit is 70% by weight. When the content of the filler is in this range, the coating properties and the like are not deteriorated, and the effects such as improvement of adhesiveness are more excellent. The lower limit of the filler content is more preferably 20% by weight, and the upper limit is more preferably 60% by weight.
本發明之液晶顯示元件用密封劑較佳含有矽烷偶合劑。上述矽烷偶合劑主要具有作為用以使密封劑與基板等良好地接著之接著助劑之作用。 The sealing compound for liquid crystal display elements of the present invention preferably 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之效果優異，藉由與硬化性樹脂化學鍵結可抑制硬化性樹脂向液晶中流出之方面而言，例如可適宜地使用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-異氰酸酯基丙基三甲氧基矽烷等。 As the above-mentioned silane coupling agent, it is excellent in the effect of improving the adhesion to the substrate, etc., and it is chemically bonded to the curable resin to suppress the outflow of the curable resin into the liquid crystal. For example, 3-aminopropyl can be suitably used. Trimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, etc.
本發明之液晶顯示元件用密封劑中之上述矽烷偶合劑含量較佳之下限為0.1重量%，較佳之上限為10重量%。藉由上述矽烷偶合劑之含量為該範圍，成為抑制液晶污染之產生，且提高接著性之效果更優異者。上述矽烷偶合劑含量更佳之下限為0.3重量%，更佳之上限為5重量%。 The lower limit of the content of the silane coupling agent in the sealing compound for liquid crystal display elements of the present invention is preferably 0.1% by weight, and the more preferable upper limit is 10% 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 adhesion is more excellent. The lower limit of the silane coupling agent content is more preferably 0.3% by weight, and the upper limit is more preferably 5% 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適宜地用作遮光密封劑。 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，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.
上述鈦黑係與對於波長300~800nm之光之平均透過率相比，對於紫外線區域附近、尤其是波長370~450nm之光之透過率提高之物質。即，上述鈦黑係具有如下性質之遮光劑：藉由充分地遮蔽可見光區域 之波長之光而對本發明之液晶顯示元件用密封劑賦予遮光性，另一方面，使紫外線區域附近之波長之光透過。作為本發明之液晶顯示元件用密封劑含有之遮光劑，較佳為絕緣性高之物質，作為絕緣性高之遮光劑，亦較佳為鈦黑。 The above-mentioned titanium black is a substance that has an improved transmittance in the vicinity of the ultraviolet region, especially light with a wavelength of 370 to 450 nm, compared with the average transmittance of light with a wavelength of 300 to 800 nm. That is, the above-mentioned titanium black is a light-shielding agent with the following properties: by sufficiently shielding the visible light region The light of the wavelength of the present invention imparts light-shielding properties to the sealing compound for liquid crystal display elements of the present invention, and on the other hand, transmits light of the wavelength near the ultraviolet region. The light-shielding agent contained in the sealing compound for liquid crystal display elements of the present invention is preferably a material with high insulation, and as a light-shielding agent with high insulation, titanium black is also preferable.
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、或經氧化矽、氧化鈦、氧化鍺、氧化鋁、氧化鋯、氧化鎂等無機成分進行被覆者等經表面處理之鈦黑。其中，就可進一步提高絕緣性之觀點而言，較佳為經有機成分進行處理者。 The above-mentioned titanium black exhibits sufficient effects even if it is not surface-treated, but it can also be treated with organic components such as coupling agents, or silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, or oxide Titanium black with surface-treated magnesium and other inorganic components. Among them, from the viewpoint that the insulation can be further improved, those treated with organic components are preferred.
又，使用含有上述鈦黑作為遮光劑之本發明之液晶顯示元件用密封劑而製造之液晶顯示元件由於具有充分之遮光性，故而可實現無漏光，具有高對比度，且具有優異之圖像顯示品質之液晶顯示元件。 In addition, the liquid crystal display element manufactured using the sealant for liquid crystal display element 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 image 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較佳之下限為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 lower limit of the specific surface area of the titanium black is preferably 13 m 2 /g, the upper limit is preferably 30 m 2 /g, the lower limit is more preferably 15 m 2 /g, and the upper limit is more preferably 25 m 2 /g.
又，上述鈦黑之體積電阻較佳之下限為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 lower limit of the volume resistance of the titanium black is preferably 0.5Ω‧cm, the upper limit is 3Ω‧cm, the lower limit is 1Ω‧cm, and the 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之距離以下，則並無特別限定，較佳之下限為1nm，較佳之上限為5000nm。藉由上述遮光劑之一次粒徑為該範圍，可製成不使所獲得之液晶顯示元件用密封劑之塗佈性等惡化，且遮光性更優異者。上述遮光劑之一次粒徑更佳 之下限為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 above-mentioned 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 5000 nm. When the primary particle diameter of the said light-shielding agent is this range, it can be set as the thing which does not deteriorate the coatability etc. of the sealing compound for liquid crystal display elements obtained, and is more excellent in light-shielding property. The primary particle size of the above sunscreen is better The lower limit is 5 nm, the more preferable upper limit is 200 nm, the more preferable lower limit is 10 nm, and the more preferable upper limit is 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)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中之上述遮光劑含量較佳之下限為5重量%，較佳之上限為80重量%。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對於基板之密接性或硬化後之強度或繪圖性降低而發揮更優異之遮光性。上述遮光劑含量更佳之下限為10重量%，更佳之上限為70重量%，進而較佳之下限為30重量%，進而較佳之上限為60重量%。 The lower limit of the content of the light-shielding agent in the sealing compound for liquid crystal display elements of the present invention is preferably 5% by weight, and a more preferable upper limit is 80% 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 reducing the adhesion of the obtained sealing compound for liquid crystal display elements to the substrate, the strength after curing, or the drawing properties. The lower limit of the sunscreen content is more preferably 10% by weight, the upper limit is more preferably 70% by weight, the lower limit is still more preferably 30% by weight, and the upper limit is more preferably 60% by weight.
本發明之液晶顯示元件用密封劑亦可視需要進而含有應力緩和劑、反應性稀釋劑、觸變劑、間隔劑、硬化促進劑、消泡劑、調平劑、聚合抑制劑、其他添加劑等。 The sealing compound for liquid crystal display elements of the present invention may further contain a stress reliever, a reactive diluent, a thixotropic agent, a spacer, a hardening accelerator, a defoamer, a leveling agent, a polymerization inhibitor, other additives, etc., if necessary.
作為製造本發明之液晶顯示元件用密封劑之方法，例如可列舉如下方法等：使用勻相分散機、均質攪拌機、萬能攪拌機、行星式混合機、捏合機、三輥研磨機等混合機，將硬化性樹脂、聚合起始劑及/或熱硬化劑、及視需要添加之矽烷偶合劑等添加劑進行混合。 As a method of manufacturing the sealant for liquid crystal display elements of the present invention, for example, the following methods can be cited: using a mixer such as a homogeneous disperser, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three-roll mill The curable resin, polymerization initiator and/or thermosetting agent, and optionally silane coupling agent and other additives are mixed.
本發明之液晶顯示元件用密封劑使用E型黏度計並於25℃、1rpm之條件測得黏度較佳之下限為5萬mPa‧s，較佳之上限為70萬mPa‧s。藉由上述黏度為該範圍，所獲得之液晶顯示元件用密封劑成為塗佈性優異者。上述黏度更佳之下限為10萬mPa‧s，更佳之上限為50萬 mPa‧s。 The sealing compound for liquid crystal display elements of the present invention uses an E-type viscometer and the viscosity is measured at 25° C. and 1 rpm. The lower limit is preferably 50,000 mPa‧s, and the upper limit is preferably 700,000 mPa‧s. When the said viscosity is this range, the obtained sealing compound for liquid crystal display elements will become one which is excellent in coatability. The lower limit of the above viscosity is more preferably 100,000 mPa‧s, and the more preferable upper limit is 500,000 mPa‧s.
再者，作為上述E型黏度計，例如可使用5XHBDV-III+CP(Brookfield公司製造，轉子No.CP-51)等。 In addition, as the E-type viscometer, for example, 5XHBDV-III+CP (manufactured by Brookfield Corporation, rotor No. CP-51) or the like can be used.
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。 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藉由樹脂微粒子優異之彈性，可無損透明基板等而進行導電連接，故而較適宜。 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 with a conductive metal layer formed on the surface of the resin particles are more suitable due to the excellent elasticity of the resin particles, which can make conductive connections 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。 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 one of this invention.
作為製造本發明之液晶顯示元件之方法，可適宜地使用液晶滴下法。具體而言，例如可列舉具有如下步驟之方法等：於ITO薄膜等附有電極之玻璃基板或聚對苯二甲酸乙二酯基板等2片基板之一片上，藉由網版印刷、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之步驟；於本發明之液晶顯示元件用密封劑未硬化之狀態下將液晶之微小滴滴下塗佈至基板之密封圖案之框內，並於真空下與另一基板重疊之步驟；及對本發明的液晶顯示元件用密封劑之密封圖案部分照射紫外線等光而使密封劑暫時硬化之步驟；及對經暫時硬化之密封劑進行加熱而進行正式硬化之步驟。 As a method of manufacturing the liquid crystal display element of this invention, a liquid crystal dropping method can be used suitably. Specifically, for example, a method having the following steps: on one of two substrates such as a glass substrate with electrodes such as an ITO film or a polyethylene terephthalate substrate, by screen printing and dispensing The step of applying the sealant for liquid crystal display elements of the present invention to form a frame-shaped sealing pattern; applying the sealant for liquid crystal display elements of the present invention to the substrate in a state where the sealant for liquid crystal display elements of the present invention is not hardened. The step of overlapping with another substrate in the frame of the sealing pattern under vacuum; and the step of irradiating the sealing pattern part of the sealing compound for liquid crystal display element of the present invention with light such as ultraviolet light to temporarily harden the sealing compound; and The hardened sealant is heated to perform a formal hardening step.
根據本發明，可提供一種塗佈性、防透濕性及接著性優異，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 coating properties, moisture permeability resistance, and adhesiveness, 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.
以下揭示實施例對本發明更詳細地加以說明，但本發明並不僅限定於該等實施例。 The following examples are disclosed to illustrate the present invention in more detail, but the present invention is not limited to these examples.
(式(1)表示之化合物(R1為H，m=n=0)之製作) (Production of the compound represented by formula (1) (R 1 is H, m=n=0))
一面吹入空氣，一面於90℃將雙酚S二環氧丙醚1000重量份、作為聚合抑制劑之對甲氧基苯酚2重量份、作為反應觸媒之三乙胺2重量份、及丙烯酸200重量份回流攪拌5小時而使該等反應。為了吸附反應物中之離子性雜質，利用填充有石英(Quartz）與高嶺土之天然結合物(HOFFMANN MINERAL公司製造、「Sillitin V85」)10重量份之管柱對所獲得之樹脂100重量份進行過濾，而獲得式(1)表示之化合物(R1為H，m=n=0)。再者，所獲得之化合物為式(1)表示之化合物(R1為H，m=n=0)係藉由1H-NMR、13C-NMR及IR進行確認。 While blowing in air, 1000 parts by weight of bisphenol S diglycidyl ether, 2 parts by weight of p-methoxyphenol as a polymerization inhibitor, 2 parts by weight of triethylamine as a reaction catalyst, and acrylic acid at 90°C 200 parts by weight was refluxed and stirred for 5 hours to cause these reactions. In order to adsorb the ionic impurities in the reactants, 100 parts by weight of the obtained resin was filtered using a column filled with 10 parts by weight of a natural combination of quartz and kaolin (manufactured by HOFFMANN MINERAL, "Sillitin V85") , And obtain the compound represented by formula (1) (R 1 is H, m=n=0). Furthermore, the obtained compound is a compound represented by formula (1) (R 1 is H, m=n=0), which was confirmed by 1 H-NMR, 13 C-NMR, and IR.
(式(1)表示之化合物(R1為H，m=n=1(平均值))之製作) (Production of the compound represented by formula (1) (R 1 is H, m=n=1 (average value)))
向安裝有溫度計、滴液漏斗、冷凝管及攪拌器之燒瓶中添加4,4'-雙(2 -羥基乙氧基)二苯基碸169重量份、表氯醇370重量份、二甲亞碸185重量份及氯化四甲基銨5重量份並於攪拌下進行溶解，再升溫至50℃。繼而，歷時100分鐘分批添加薄片狀之氫氧化鈉60重量份後，進而於50℃進行後續反應3小時。反應結束後，添加水400重量份進行水洗，並使用旋轉蒸發器，於130℃、減壓下，自油層將過量之表氯醇等蒸餾去除。向殘留物中添加甲基異丁基酮450重量份並進行溶解，再升溫至70℃。於攪拌下添加30%之氫氧化鈉水溶液10重量份，並反應1小時，然後進行3次水洗，使用旋轉蒸發器，於180℃、減壓下，將甲基異丁基酮蒸餾去除。一面吹入空氣，一面於90℃將所獲得之反應物1100重量份、作為聚合抑制劑之對甲氧基苯酚2重量份、作為反應觸媒之三乙胺2重量份、及丙烯酸200重量份回流攪拌5小時而使該等反應。為了吸附反應物中之離子性雜質，利用填充有石英與高嶺土之天然結合物(HOFFMANN MINERAL公司製造、「Sillitin V85」)10重量份之管柱對所獲得之樹脂100重量份進行過濾，而獲得式(1)表示之化合物(R1為H，m=n=1(平均值))。再者，所獲得之化合物為式(1)表示之化合物(R1為H，m=n=1(平均值))係藉由1H-NMR、13C-NMR及IR進行確認。 Add 169 parts by weight of 4,4'-bis(2-hydroxyethoxy)diphenyl sulfide, 370 parts by weight of epichlorohydrin, and dimethylsulfoxide to a flask equipped with a thermometer, dropping funnel, condenser and stirrer. 185 parts by weight of ash and 5 parts by weight of tetramethylammonium chloride were dissolved under stirring, and the temperature was increased to 50°C. Then, after adding 60 parts by weight of flaky sodium hydroxide in batches over 100 minutes, the subsequent reaction was further performed at 50° C. for 3 hours. After the completion of the reaction, 400 parts by weight of water was added for washing, and using a rotary evaporator, the excess epichlorohydrin and the like were distilled off from the oil layer at 130° C. under reduced pressure. To the residue, 450 parts by weight of methyl isobutyl ketone was added and dissolved, and the temperature was increased to 70°C. 10 parts by weight of a 30% sodium hydroxide aqueous solution was added under stirring, and reacted for 1 hour, and then washed with water three times. Using a rotary evaporator, the methyl isobutyl ketone was distilled off at 180° C. under reduced pressure. While blowing in air, 1100 parts by weight of the obtained reactant, 2 parts by weight of p-methoxyphenol as a polymerization inhibitor, 2 parts by weight of triethylamine as a reaction catalyst, and 200 parts by weight of acrylic acid were blown in at 90°C It was refluxed and stirred for 5 hours to cause the reaction. In order to adsorb ionic impurities in the reactants, 100 parts by weight of the obtained resin was filtered using a column filled with 10 parts by weight of the natural combination of quartz and kaolin (manufactured by HOFFMANN MINERAL, "Sillitin V85"), and obtained The compound represented by formula (1) (R 1 is H, m=n=1 (average value)). Furthermore, the obtained compound is a compound represented by formula (1) (R 1 is H, m=n=1 (average value)), which was confirmed by 1 H-NMR, 13 C-NMR, and IR.
(實施例1~7及比較例1~4) (Examples 1 to 7 and Comparative Examples 1 to 4)
依據表1記載之摻合比，使用行星式攪拌機(新基公司製造、「脫泡練太郎」)將各材料混合後，進而使用三輥研磨機進行混合，藉此製備實施例1~7及比較例1~4之液晶顯示元件用密封劑。 According to the blending ratio described in Table 1, the materials were mixed using a planetary mixer (manufactured by Shinki Corporation, "Defoaming Nentaro"), and then mixed using a three-roll mill to prepare Examples 1-7 and The sealing compounds for liquid crystal display elements of Comparative Examples 1 to 4.
<評價> <evaluation>
對實施例及比較例獲得之液晶顯示元件用密封劑進行以下之評價。將 結果示於表1。 The following evaluation was performed about the sealing compound for liquid crystal display elements obtained by the Example and the comparative example. will The results are shown in Table 1.
(塗佈性) (Coatability)
使用分注器(武藏工業公司製造、「SHOTMASTER300」)，將實施例及比較例獲得之各液晶顯示元件用密封劑塗佈於玻璃基板上。於將分注噴嘴固定為400μm、將噴嘴間隙固定為30μm，且將吐出壓固定為300kPa而進行塗佈時，將不存在模糊或滴液而成功進行塗佈之情形評價為「◎」，將略微產生模糊或滴液之情形評價為「○」，將雖然無塗佈裂紋但產生較大之模糊或滴液之情形評價為「△」，將產生塗佈裂紋或完全無法塗佈之情形評價為「×」，從而對塗佈性進行評價。 Using a dispenser (manufactured by Musashi Kogyo Co., Ltd., "SHOTMASTER 300"), each of the sealing compounds for liquid crystal display elements obtained in Examples and Comparative Examples was applied on a glass substrate. When the dispensing nozzle is fixed to 400μm, the nozzle gap is fixed to 30μm, and the discharge pressure is fixed to 300kPa for coating, the successful coating without blur or dripping is evaluated as "◎". Slight blur or dripping is evaluated as "○", while there is no coating crack but large blur or dripping is evaluated as "△", and coating cracks or no coating at all are evaluated It is "×" to evaluate the coatability.
(接著性) (Adhesion)
藉由行星式攪拌裝置，使相對於實施例及比較例獲得之各液晶顯示元件用密封劑100重量份，平均粒徑5μm之間隔粒子(積水化學工業公司製造、「Micropearl SP-2050」)1重量份均勻地分散，並取極微量置於康寧玻璃1737(20mm×50mm×厚度0.7mm)之中央部，使同型之玻璃重疊於其上而使液晶顯示元件用密封劑展開，使用金屬鹵素燈照射100mW/cm2之紫外線30秒，然後於120℃下加熱1小時使密封劑硬化，而獲得接著試片。 Using a planetary stirring device, spacer particles with an average particle diameter of 5 μm (manufactured by Sekisui Chemical Industry Co., Ltd., "Micropearl SP-2050") with respect to 100 parts by weight of each liquid crystal display element sealant obtained in Examples and Comparative Examples were made 1 The weight is evenly dispersed, and a very small amount is placed in the center of Corning Glass 1737 (20mm×50mm×thickness 0.7mm), and the same type of glass is overlapped on it to expand the sealant for liquid crystal display elements. Use a metal halide lamp 100 mW/cm 2 ultraviolet rays were irradiated for 30 seconds, and then heated at 120° C. for 1 hour to harden the sealant, thereby obtaining an adhesive test piece.
使用張力計，對所獲得之接著試片測定接著強度。用所獲得之測定值(kgf)除以密封塗佈截面積(cm2)，將所得之值為35kgf/cm2以上之情形評價為「◎」，將為30kgf/cm2以上且未達35kgf/cm2之情形評價為「○」，將為25kgf/cm2以上且未達30kgf/cm2之情形評價為「△」，將未達25kgf/cm2之情形評價為「×」，從而對接著性進行評價。 Using a tensiometer, the adhesive strength of the obtained adhesive test piece was measured. The measured value obtained by the (kgf) divided by the cross sectional area of the seal-coated (cm & lt 2), the case of 2 or more is obtained from 35kgf / cm was evaluated as "◎" will be 2 or more and less than 35kgf 30kgf / cm / cm 2 of the case was evaluated as "○" will 25kgf / cm 2 or more and less than 30kgf / cm 2 of the case was evaluated as "△" will be less than 25kgf / cm 2 of the case was evaluated as "×", thus Follow-up evaluation.
(防透濕性) (Anti-moisture permeability)
將實施例及比較例獲得之各液晶顯示元件用密封劑於平滑之脫模膜狀利用塗佈機塗敷為厚度200~300μm後，使用金屬鹵素燈照射100mW/cm2之紫外線30秒，然後於120℃加熱1小時，藉此獲得透濕度測定用硬化膜。 The sealants for liquid crystal display elements obtained in the examples and comparative examples were applied to a smooth release film with a thickness of 200 to 300 μm using a coater, and then irradiated with 100 mW/cm 2 of ultraviolet light for 30 seconds using a metal halide lamp, and then By heating at 120°C for 1 hour, a cured film for measuring moisture permeability was obtained.
藉由依據JIS Z 0208之防濕包裝材料之透濕度試驗方法(杯式法)的方法製作透濕度試驗用杯，並設置所獲得之透濕度測定用硬化膜，投入至溫度80℃濕度90%RH之恆溫恆濕烘箱中，而對透濕度進行測定。將獲得之透濕度之值未達60g/m2‧24hr之情形評價為「◎」，將為60g/m2‧24hr以上且未達100g/m2‧24hr之情形評價為「○」，將為100g/m2‧24hr以上且未達120g/m2‧24hr之情形評價為「△」，將為120g/m2‧24hr以上之情形評價為「×」，從而對防透濕性進行評價。 The moisture permeability test cup is made by the method based on the moisture permeability test method of moisture-proof packaging materials (cup method) in JIS Z 0208, and the obtained cured film for moisture permeability measurement is set, and the temperature is 80℃ and the humidity is 90%. In the constant temperature and humidity oven of RH, the moisture permeability is measured. The obtained value of the moisture permeability less than the case of 60g / m 2 ‧24hr it was evaluated as "◎" will be 60g / m 2 ‧24hr case more and less than 100g / m 2 ‧24hr it was evaluated as "○", will be The case of 100g/m 2 ‧24hr or more and less than 120g/m 2 ‧24hr is evaluated as "△", and the case of 120g/m 2 ‧24hr or more is evaluated as "×" to evaluate the moisture permeability .
(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，使相對於實施例及比較例獲得之各液晶顯示元件用密封劑100重量份，平均粒徑5μm之間隔粒子(積水化學工業公司製造、「Micropearl SP-2050」)1重量份均勻地分散，將所獲得之密封劑填充至分注用注射器(武藏工業公司製造、「PSY-10E」)中，於進行消泡處理後，利用分注器(武藏工業公司製造、「SHOTMASTER300」)將密封劑以框狀塗佈於2片附有ITO薄膜之透明電極基板之一者。繼而，利用液晶滴下裝置將TN液晶(智索公司製造、「JC-5001LA」)之微小滴滴下塗佈至密封劑之框內，並利用真空貼合裝置將另一片透明電極基板於5Pa之真空下貼合，而獲得單元。使用金屬鹵素燈，對所獲得之單元照射100mW/cm2之紫外線30秒，然後於120℃加熱1小時使密封劑硬化，而獲得液晶顯示元件。 Using a planetary stirring device, 1 weight of spacer particles ("Micropearl SP-2050" manufactured by Sekisui Chemical Co., Ltd., "Micropearl SP-2050") with an average particle diameter of 5 μm relative to 100 parts by weight of each liquid crystal display element sealing compound obtained in the examples and comparative examples The sealant is evenly dispersed, and the obtained sealant is filled into a dispensing syringe (manufactured by Musashi Kogyo Co., Ltd., "PSY-10E"), and after defoaming treatment, a dispenser (manufactured by Musashi Kogyo Co., Ltd., "SHOTMASTER 300 ") Apply the sealant in a frame shape to one of two transparent electrode substrates with ITO film. Then, use the liquid crystal dropping device to drop the tiny drops of TN liquid crystal (manufactured by Chisso Corporation, "JC-5001LA") into the sealant frame, and use the vacuum bonding device to place another transparent electrode substrate in a vacuum of 5 Pa Attach the bottom to obtain the unit. Using a metal halide lamp, the obtained cell was irradiated with ultraviolet light of 100 mW/cm 2 for 30 seconds, and then heated at 120° C. for 1 hour to harden the sealant to obtain a liquid crystal display element.
針對所獲得之液晶顯示元件，對在密封部周邊之液晶(尤其是角部)所產生之顯示不均進行目測觀察，將未確認到顯示不均之情形評價為「◎」，將確認到略微之顯示不均之情形評價為「○」，將明確地確認到顯示不均之情形評價為「△」，將確認到嚴重之顯示不均之情形評價為「×」，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, visual observation was made on the display unevenness of the liquid crystal around the sealing part (especially the corners), and the situation where the display unevenness was not confirmed was evaluated as "◎", and slightly confirmed The display unevenness is evaluated as "○", the clearly confirmed display unevenness is evaluated as "△", the severe display unevenness is confirmed as "×", and the liquid crystal display element is displayed Performance (low liquid crystal contamination) was evaluated.
再者，評價為「◎」」、「○」之液晶顯示元件為實用上完全無問題之等級。 Furthermore, the liquid crystal display elements evaluated as "◎"" and "○" are of a practically no problem level.
[產業上之可利用性] [Industrial availability]
根據本發明，可提供一種塗佈性、防透濕性及接著性優異，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 coating properties, moisture permeability resistance, and adhesiveness, 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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