TWI849163B - Sealant for display element, upper and lower conductive material, and display element - Google Patents
Sealant for display element, upper and lower conductive material, and display element Download PDFInfo
- Publication number
- TWI849163B TWI849163B TW109121873A TW109121873A TWI849163B TW I849163 B TWI849163 B TW I849163B TW 109121873 A TW109121873 A TW 109121873A TW 109121873 A TW109121873 A TW 109121873A TW I849163 B TWI849163 B TW I849163B
- Authority
- TW
- Taiwan
- Prior art keywords
- meth
- sealant
- acrylate
- display element
- manufactured
- Prior art date
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- 239000000565 sealant Substances 0.000 title claims abstract description 83
- 239000004020 conductor Substances 0.000 title claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 30
- 239000011347 resin Substances 0.000 claims abstract description 30
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 21
- 230000009477 glass transition Effects 0.000 claims abstract description 20
- 238000012360 testing method Methods 0.000 claims abstract description 14
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 98
- -1 methacrylic acid-modified bisphenol A Chemical class 0.000 claims description 82
- 239000004593 Epoxy Substances 0.000 claims description 78
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 26
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 12
- 239000011859 microparticle Substances 0.000 claims description 7
- 230000005484 gravity Effects 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 99
- 239000004973 liquid crystal related substance Substances 0.000 description 25
- 239000000126 substance Substances 0.000 description 22
- 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 21
- 238000001723 curing Methods 0.000 description 19
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 15
- 239000010936 titanium Substances 0.000 description 15
- 229910052719 titanium Inorganic materials 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 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 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 239000006087 Silane Coupling Agent Substances 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 10
- 150000007524 organic acids Chemical class 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 238000010538 cationic polymerization reaction Methods 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 230000000475 sunscreen effect Effects 0.000 description 4
- 239000000516 sunscreening agent Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- 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
- 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 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000003292 glue 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-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
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 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 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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- LOCXTTRLSIDGPS-FVDSYPCUSA-N [(z)-[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(/CCCCCC)=N\OC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-FVDSYPCUSA-N 0.000 description 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
- 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
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 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
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler 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
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000005641 methacryl group Chemical group 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 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
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- ZNGSVRYVWHOWLX-KHFUBBAMSA-N (1r,2s)-2-(methylamino)-1-phenylpropan-1-ol;hydrate Chemical compound O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 ZNGSVRYVWHOWLX-KHFUBBAMSA-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
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- CYXLGABBVLIUJZ-UHFFFAOYSA-N 2-(2-hydroxypropoxycarbonyl)benzoic acid Chemical compound CC(O)COC(=O)C1=CC=CC=C1C(O)=O CYXLGABBVLIUJZ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- LESMLVDJJCWZAJ-UHFFFAOYSA-N 2-(diphenylphosphorylmethyl)-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 LESMLVDJJCWZAJ-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
- RUVNKAUVVBCURD-UHFFFAOYSA-N 2-[[4-[2-[4-(oxiran-2-ylmethoxy)-3-prop-2-enylphenyl]propan-2-yl]-2-prop-2-enylphenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C(CC=C)=CC=1C(C)(C)C(C=C1CC=C)=CC=C1OCC1CO1 RUVNKAUVVBCURD-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
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- 229910052602 gypsum Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
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- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- LBUSGXDHOHEPQQ-UHFFFAOYSA-N propane-1,1,1-triol Chemical compound CCC(O)(O)O LBUSGXDHOHEPQQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
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- 238000012552 review Methods 0.000 description 1
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- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Liquid Crystal (AREA)
- Sealing Material Composition (AREA)
- Electroluminescent Light Sources (AREA)
- Epoxy Resins (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
本發明之目的在於提供一種能夠獲得高溫高濕環境下之可靠性優異之顯示元件之顯示元件用密封劑。又，本發明之目的在於提供一種使用該顯示元件用密封劑而成之上下導通材料及顯示元件。 本發明係一種顯示元件用密封劑，其含有硬化性樹脂以及聚合起始劑及/或熱硬化劑，硬化物之玻璃轉移溫度為125℃以上，且對硬化物進行於121℃、100%RH、2 atm之環境下暴露48小時之高溫高濕試驗後之硬化收縮率為5%以下。The purpose of the present invention is to provide a sealant for display elements that can obtain a display element with excellent reliability in a high temperature and high humidity environment. In addition, the purpose of the present invention is to provide an upper and lower conductive material and a display element formed using the sealant for display elements. The present invention is a sealant for display elements, which contains a curable resin and a polymerization initiator and/or a thermosetting agent, and the glass transition temperature of the cured product is above 125°C, and the cured product is exposed to a high temperature and high humidity test of 121°C, 100%RH, and 2 atm for 48 hours. The curing shrinkage rate is less than 5%.
Description
本發明係關於一種能夠獲得高溫高濕環境下之可靠性優異之顯示元件之顯示元件用密封劑。又，本發明係關於一種使用該顯示元件用密封劑而成之上下導通材料及顯示元件。The present invention relates to a sealant for display element that can obtain a display element with excellent reliability in a high temperature and high humidity environment. In addition, the present invention relates to an upper and lower conductive material and a display element formed by using the sealant for display element.
近年來，作為具有薄型、輕量、低耗電等特徵之顯示元件，廣泛利用液晶顯示元件或有機EL顯示元件等。於該等顯示元件中，通常利用使用硬化性樹脂組成物而成之密封劑進行液晶或發光層等之密封。 例如，作為液晶顯示元件，就產距時間（Tact Time）縮短、使用液晶量之最佳化等觀點而言，揭示有如專利文獻1、專利文獻2中所揭示之使用光熱併用硬化型密封劑之液晶顯示元件。In recent years, liquid crystal display elements or organic EL display elements have been widely used as display elements with the characteristics of thinness, lightness, and low power consumption. In such display elements, a sealant made of a curable resin composition is usually used to seal the liquid crystal or the light-emitting layer. For example, as a liquid crystal display element, from the perspective of shortening the tact time and optimizing the amount of liquid crystal used, a liquid crystal display element using a light-heat curing sealant as disclosed in Patent Documents 1 and 2 is disclosed.
又，對於顯示元件，作為於高溫高濕環境下驅動等時之高度可靠性，亦要求適應121℃、100%RH、2 atm之條件下之壓力鍋試驗（PCT）之性能。為了獲得具有高度可靠性之顯示元件，需要使密封劑為耐濕熱性優異者。 先前技術文獻 專利文獻In addition, for display components, in order to achieve high reliability when driven in a high temperature and high humidity environment, the performance of the pressure cooker test (PCT) under the conditions of 121°C, 100%RH, and 2 atm is also required. In order to obtain a display component with high reliability, the sealant needs to be excellent in moisture and heat resistance. Previous technical literature Patent literature
專利文獻1：日本特開2001-133794號公報 專利文獻2：國際公開第02/092718號Patent document 1: Japanese Patent Publication No. 2001-133794 Patent document 2: International Publication No. 02/092718
[發明所欲解決之課題][The problem that the invention wants to solve]
本發明之目的在於提供一種能夠獲得高溫高濕環境下之可靠性優異之顯示元件之顯示元件用密封劑。又，本發明之目的在於提供一種使用該顯示元件用密封劑而成之上下導通材料及顯示元件。 [解決課題之技術手段]The purpose of the present invention is to provide a sealant for display elements that can obtain a display element with excellent reliability in a high temperature and high humidity environment. In addition, the purpose of the present invention is to provide an upper and lower conductive material and a display element formed by using the sealant for display elements. [Technical means to solve the problem]
本發明係一種顯示元件用密封劑，其含有硬化性樹脂以及聚合起始劑及/或熱硬化劑，硬化物之玻璃轉移溫度為125℃以上，對硬化物進行於121℃、100%RH、2 atm之環境下暴露48小時之高溫高濕試驗後之硬化收縮率為5%以下。 以下對本發明進行詳述。The present invention is a sealant for display elements, which contains a curable resin and a polymerization initiator and/or a thermosetting agent. The glass transition temperature of the cured product is above 125°C, and the curing shrinkage rate of the cured product after being exposed to a high temperature and high humidity test at 121°C, 100%RH, and 2 atm for 48 hours is below 5%. The present invention is described in detail below.
本發明人對於在高溫高濕環境下驅動時產生顯示不良之顯示元件進行了確認，結果確認到顯示元件中有氣泡侵入。因此，本發明人對於使顯示元件用密封劑之硬化物之玻璃轉移溫度成為特定值以上，並且使進行於121℃、100%RH、2 atm之環境下暴露48小時之高溫高濕試驗後之硬化物之硬化收縮率成為特定值以下進行了研究。其結果，發現可獲得能夠抑制氣泡侵入，從而能夠獲得高溫高濕環境下之可靠性優異之顯示元件之顯示元件用密封劑，從而完成了本發明。 本發明之顯示元件用密封劑之能夠獲得高溫高濕環境下之可靠性優異之顯示元件之效果於將本發明之顯示元件用密封劑用作液晶顯示元件用密封劑之情形時得到尤其顯著的發揮。The inventors of the present invention have confirmed that display elements that have poor display when driven in a high temperature and high humidity environment have bubbles intruding into the display elements. Therefore, the inventors of the present invention have studied how to make the glass transition temperature of the cured product of the sealant for display elements above a specific value, and how to make the curing shrinkage rate of the cured product after being exposed to a high temperature and high humidity test for 48 hours at 121°C, 100%RH, and 2 atm below a specific value. As a result, it was found that a sealant for display elements that can suppress bubble intrusion and thus obtain a display element with excellent reliability in a high temperature and high humidity environment can be obtained, thereby completing the present invention. The effect of the sealant for display element of the present invention in obtaining a display element with excellent reliability in a high temperature and high humidity environment is particularly significantly exerted when the sealant for display element of the present invention is used as a sealant for a liquid crystal display element.
本發明之顯示元件用密封劑之硬化物之玻璃轉移溫度之下限為125℃。藉由上述硬化物之玻璃轉移溫度為125℃以上，並且下述硬化收縮率為5%以下，所獲得之顯示元件用密封劑成為抑制高溫高濕環境下之氣泡侵入之效果優異者。上述硬化物之玻璃轉移溫度之較佳之下限為130℃，更佳之下限為135℃。 又，就接著性之觀點而言，上述硬化物之玻璃轉移溫度之較佳之上限為160℃。 再者，於本說明書中，上述「玻璃轉移溫度」意指藉由動態黏彈性測定所獲得之損耗正切（tanδ）之極大值中之起因於微布朗運動之極大值出現時之溫度。上述玻璃轉移溫度可利用使用動態黏彈性測定裝置等之以往公知之方法進行測定。 又，作為測定上述玻璃轉移溫度之硬化物，使用利用金屬鹵化物燈對密封劑照射30秒100 mW/cm2 之紫外線（波長365 nm）後，於120℃加熱1小時使其硬化而獲得者。The lower limit of the glass transition temperature of the cured product of the sealant for display elements of the present invention is 125°C. By setting the glass transition temperature of the cured product to be above 125°C and the curing shrinkage rate to be below 5%, the sealant for display elements obtained is excellent in suppressing the intrusion of bubbles in a high temperature and high humidity environment. The preferred lower limit of the glass transition temperature of the cured product is 130°C, and the more preferred lower limit is 135°C. In addition, from the perspective of adhesion, the preferred upper limit of the glass transition temperature of the cured product is 160°C. Furthermore, in this specification, the "glass transition temperature" refers to the temperature at which the maximum value of the loss tangent (tanδ) obtained by dynamic viscoelasticity measurement due to micro-Brownian motion appears. The glass transition temperature can be measured by a conventionally known method using a dynamic viscoelasticity measuring device, etc. In addition, as a hardened material for measuring the glass transition temperature, a sealant is irradiated with ultraviolet light (wavelength 365 nm) of 100 mW/ cm2 for 30 seconds using a metal halide lamp, and then heated at 120°C for 1 hour to harden.
本發明之顯示元件用密封劑於對硬化物進行於121℃、100%RH、2 atm之環境下暴露48小時之高溫高濕試驗後之硬化收縮率之上限為5%。藉由上述硬化收縮率為5%以下，並且上述硬化物之玻璃轉移溫度為125℃以上，所獲得之顯示元件用密封劑成為抑制高溫高濕環境下之氣泡侵入之效果優異者。上述硬化收縮率之較佳之上限為4.8%，更佳之上限為4.5%。 又，上述硬化收縮率並不特別存在較佳之下限，但實質之下限為3%。 再者，於本說明書中，上述「硬化收縮率」係於將硬化前之顯示元件用密封劑於25℃之比重設為GA ，將高溫高濕試驗後之硬化物於25℃之比重設為GB 時，利用下述式算出之值。 硬化收縮率（%）＝（（GB －GA ）/GB ）×100 又，作為進行上述高溫高濕試驗之硬化物，使用對密封劑照射30秒100 mW/cm2 之紫外線後，於120℃加熱1小時使其硬化而獲得者。The upper limit of the curing shrinkage rate of the sealant for display components of the present invention after the cured product is exposed to a high temperature and high humidity test of 121°C, 100%RH, and 2 atm for 48 hours is 5%. By making the above curing shrinkage rate less than 5% and the glass transition temperature of the above cured product greater than 125°C, the sealant for display components obtained has an excellent effect of inhibiting the intrusion of bubbles in a high temperature and high humidity environment. The upper limit of the above curing shrinkage rate is preferably 4.8%, and the upper limit is more preferably 4.5%. In addition, the above curing shrinkage rate does not particularly have a better lower limit, but the actual lower limit is 3%. In this specification, the above-mentioned "curing shrinkage rate" is a value calculated by the following formula when the specific gravity of the display element sealant before curing at 25°C is set as GA and the specific gravity of the cured product after the high temperature and high humidity test at 25°C is set as GB . Curing shrinkage rate (%) = (( GB - GA )/ GB ) × 100 In addition, as the cured product subjected to the above-mentioned high temperature and high humidity test, the sealant was irradiated with ultraviolet rays of 100 mW/ cm2 for 30 seconds and then heated at 120°C for 1 hour to cure.
作為藉由使用本發明之顯示元件用密封劑能夠抑制氣泡侵入之理由，考慮以下理由。 即，認為由於上述高溫高濕環境下之硬化收縮而硬化物中產生水分滲入之路徑，自該路徑滲入之水分成為水蒸氣而產生氣泡。推測由於本發明之顯示元件用密封劑除上述硬化物之玻璃轉移溫度為125℃以上之外，進行上述高溫高濕試驗後之硬化收縮率為5%以下，故而此種路徑之形成得到抑制。The following reasons are considered as the reason why the sealant for display elements of the present invention can suppress the intrusion of bubbles. That is, it is believed that due to the curing shrinkage in the high temperature and high humidity environment, a path for water penetration is generated in the hardened material, and the water that penetrates from the path is converted into water vapor to generate bubbles. It is speculated that since the sealant for display elements of the present invention has a glass transition temperature of 125°C or more and a curing shrinkage rate of 5% or less after the high temperature and high humidity test, the formation of such a path is suppressed.
於本發明之顯示元件用密封劑中，作為將上述硬化物之玻璃轉移溫度及上述硬化收縮率分別設為上述範圍之方法，較佳為對顯示元件用密封劑中所含有之各構成成分之種類及其含有比率進行調整之方法。 作為將上述硬化物之玻璃轉移溫度設為上述範圍之方法，例如考慮使用具有雙酚A型骨架等較硬骨架之硬化性樹脂、使用多官能之硬化性樹脂以提高交聯密度、提高下述甲基丙烯酸比率等方法，但並不限定於該等方法。又，作為將上述硬化收縮率設為上述範圍之方法，例如考慮降低硬化性樹脂之交聯密度、降低下述硬化性樹脂中之(甲基)丙烯醯基與環氧基之合計中之(甲基)丙烯醯基之含有比率等方法，但並不限定於該等方法。In the sealant for display elements of the present invention, as a method for setting the glass transition temperature of the above-mentioned cured product and the above-mentioned curing shrinkage rate to the above-mentioned ranges, it is preferable to adjust the types and content ratios of the components contained in the sealant for display elements. As a method for setting the glass transition temperature of the above-mentioned cured product to the above-mentioned range, for example, a method of using a hardening resin having a harder skeleton such as a bisphenol A type skeleton, using a multifunctional hardening resin to increase the crosslinking density, and increasing the ratio of the following methacrylic acid can be considered, but it is not limited to these methods. As a method for setting the curing shrinkage ratio to the above range, for example, reducing the crosslinking density of the curable resin, reducing the content ratio of the (meth)acryl group in the total of the (meth)acryl group and the epoxy group in the curable resin described below, etc. can be considered, but the invention is not limited to these methods.
本發明之顯示元件用密封劑含有硬化性樹脂。 上述硬化性樹脂較佳為含有具有(甲基)丙烯醯基之化合物。 藉由含有上述具有(甲基)丙烯醯基之化合物，於將所獲得之顯示元件用密封劑用作液晶顯示元件用密封劑之情形時，成為低液晶污染性優異者。其中，就容易將上述玻璃轉移溫度設為上述範圍之方面而言，上述硬化性樹脂更佳為含有具有甲基丙烯醯基之化合物。 再者，於本說明書中，上述「(甲基)丙烯醯基」意指丙烯醯基或甲基丙烯醯基。The sealant for display elements of the present invention contains a curable resin. The curable resin preferably contains a compound having a (meth)acryl group. By containing the compound having a (meth)acryl group, when the sealant for display elements obtained is used as a sealant for liquid crystal display elements, it becomes excellent in low liquid crystal contamination. Among them, in terms of facilitating the setting of the glass transition temperature to the above range, the curable resin preferably contains a compound having a methacryl group. Furthermore, in this specification, the "(meth)acryl group" means an acryl group or a methacryl group.
於上述硬化性樹脂含有上述具有甲基丙烯醯基之化合物之情形時，較佳為下述式（I）所表示之甲基丙烯酸比率為0.5以上。藉由上述甲基丙烯酸比率為0.5以上，更容易將上述玻璃轉移溫度設為上述範圍。更佳為上述甲基丙烯酸比率為0.6以上。 甲基丙烯酸比率＝（WM /EM ）/（WA /EA ＋WM /EM ） （I） 式（I）中，EA 為具有丙烯醯基之化合物之丙烯醯基當量（g/mol），EM 為具有甲基丙烯醯基之化合物之甲基丙烯醯基當量（g/mol），WA 為具有丙烯醯基之化合物之含量（重量份），WM 為具有甲基丙烯醯基之化合物之含量（重量份）。 再者，上述「丙烯醯基當量」係將具有丙烯醯基之化合物之重量（g）除以該具有丙烯醯基之化合物中所含有之丙烯醯基之莫耳數（mol）而求出之值。於上述硬化性樹脂含有複數種上述具有丙烯醯基之化合物（A1、A2、…）之情形時，上述式（I）中之「WA /EA 」意指對於各具有丙烯醯基之化合物將具有丙烯醯基之化合物之含量除以丙烯醯基當量而求出之值之合計（WA1 /EA1 ＋WA2 /EA2 ＋…）。於上述硬化性樹脂不含有上述具有丙烯醯基之化合物之情形時，將上述式（I）中之「WA /EA 」設為0。 又，上述「甲基丙烯醯基當量」係將具有甲基丙烯醯基之化合物之重量（g）除以該具有甲基丙烯醯基之化合物中所含有之甲基丙烯醯基之莫耳數（mol）而求出之值。於上述硬化性樹脂含有複數種上述具有甲基丙烯醯基之化合物（M1、M2、…）之情形時，上述式（I）中之「WM /EM 」意指對於各具有甲基丙烯醯基之化合物將具有甲基丙烯醯基之化合物之含量除以甲基丙烯醯基當量而求出之值之合計（WM1 /EM1 ＋WM2 /EM2 ＋…）。When the curable resin contains the compound having a methacrylic group, the methacrylic acid ratio represented by the following formula (I) is preferably 0.5 or more. When the methacrylic acid ratio is 0.5 or more, it is easier to set the glass transition temperature to the above range. More preferably, the methacrylic acid ratio is 0.6 or more. Methacrylic acid ratio = (W M / EM ) / ( WA / EA + W M / EM ) (I) In formula (I), EA is the acryl equivalent (g/mol) of the compound having an acryl group, EM is the methacrylic acid equivalent (g/mol) of the compound having a methacrylic group, WA is the content (parts by weight) of the compound having an acryl group, and WM is the content (parts by weight) of the compound having a methacrylic group. The "acryl equivalent" is a value obtained by dividing the weight (g) of the compound having an acryl group by the mole (mol) of the acryl group contained in the compound having an acryl group. When the curable resin contains a plurality of the compounds having an acryl group (A1, A2, ...), " WA / EA " in the formula (I) means the sum of the values obtained by dividing the content of the compound having an acryl group by the acryl equivalent for each compound having an acryl group ( WA1 / EA1 + WA2 / EA2 +...). When the curable resin does not contain the compound having an acryl group, " WA / EA " in the formula (I) is set to 0. The above-mentioned "methacrylic acid equivalent" is a value obtained by dividing the weight (g) of the compound having a methacrylic acid group by the mole number (mol) of the methacrylic acid group contained in the compound having a methacrylic acid group. When the above-mentioned curable resin contains a plurality of the above-mentioned compounds having a methacrylic acid group (M1, M2, ...), "W M / EM " in the above-mentioned formula (I) means the total value obtained by dividing the content of the compound having a methacrylic acid group by the methacrylic acid equivalent for each compound having a methacrylic acid group (W M1 / EM1 +W M2 / EM2 + ...).
作為上述具有(甲基)丙烯醯基之化合物，例如可列舉：部分(甲基)丙烯酸改質環氧化合物、環氧(甲基)丙烯酸酯、(甲基)丙烯酸酯化合物、(甲基)丙烯酸胺酯（urethane (meth)acrylate）等。其中，就更容易將上述硬化物之玻璃轉移溫度及上述硬化收縮率分別設為上述範圍之方面而言，上述硬化性樹脂較佳為含有部分甲基丙烯酸改質環氧化合物，更佳為含有部分甲基丙烯酸改質雙酚A型環氧化合物。 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。又，上述「部分(甲基)丙烯酸改質環氧化合物」意指可藉由使具有2個以上環氧基之化合物之一部分環氧基與(甲基)丙烯酸進行反應而獲得之1分子中分別具有1個以上環氧基及(甲基)丙烯醯基之化合物。進而，上述「(甲基)丙烯酸酯」意指丙烯酸酯或甲基丙烯酸酯，上述「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)丙烯酸進行反應所得之化合物。As the above-mentioned compound having a (meth)acrylic group, for example, there can be listed: partially (meth)acrylic modified epoxy compounds, epoxy (meth)acrylates, (meth)acrylate compounds, (meth)acrylic amine esters (urethane (meth)acrylate), etc. Among them, in terms of making it easier to set the glass transition temperature of the above-mentioned hardened material and the above-mentioned hardening shrinkage rate to the above-mentioned ranges, the above-mentioned curable resin is preferably a partially methacrylic modified epoxy compound, and more preferably a partially methacrylic modified bisphenol A type epoxy compound. In addition, in this specification, the above-mentioned "(meth)acrylic acid" means acrylic acid or methacrylic acid. In addition, the above-mentioned "partial (meth)acrylic acid modified epoxy compound" means a compound having one or more epoxy groups and (meth)acrylic acid groups in one molecule, which can be obtained by reacting a part of the epoxy groups of a compound having two or more epoxy groups with (meth)acrylic acid. Furthermore, the above-mentioned "(meth)acrylate" means acrylate or methacrylate, and the above-mentioned "epoxy (meth)acrylate" means a compound obtained by reacting all the epoxy groups in an epoxy compound with (meth)acrylic acid.
作為成為用以合成上述部分(甲基)丙烯酸改質環氧化合物之原料之環氧化合物，例如可列舉：雙酚A型環氧化合物、雙酚F型環氧化合物、雙酚S型環氧化合物、2,2'-二烯丙基雙酚A型環氧化合物、氫化雙酚型環氧化合物、環氧丙烷加成雙酚A型環氧化合物、間苯二酚型環氧化合物、聯苯型環氧化合物、硫醚型環氧化合物、二苯醚型環氧化合物、二環戊二烯型環氧化合物、萘型環氧化合物、酚系酚醛清漆型環氧化合物、鄰甲酚酚醛清漆型環氧化合物、二環戊二烯酚醛清漆型環氧化合物、聯苯酚醛清漆型環氧化合物、萘酚酚醛清漆型環氧化合物、環氧丙胺型環氧化合物、烷基多元醇型環氧化合物、橡膠改質型環氧化合物、環氧丙酯化合物等。Examples of the epoxy compounds used as raw materials for synthesizing the partially (meth)acrylic acid modified epoxy compounds include bisphenol A epoxy compounds, bisphenol F epoxy compounds, bisphenol S epoxy compounds, 2,2'-diallylbisphenol A epoxy compounds, hydrogenated bisphenol epoxy compounds, propylene oxide addition bisphenol A epoxy compounds, resorcinol epoxy compounds, biphenyl epoxy compounds, thioether epoxy compounds, compounds, diphenyl ether type epoxy compounds, dicyclopentadiene type epoxy compounds, naphthalene type epoxy compounds, phenol novolac type epoxy compounds, o-cresol novolac type epoxy compounds, dicyclopentadiene novolac type epoxy compounds, biphenyl novolac type epoxy compounds, naphthol novolac type epoxy compounds, epoxy propylamine type epoxy compounds, alkyl polyol type epoxy compounds, rubber modified epoxy compounds, epoxy propyl ester compounds, etc.
作為上述雙酚A型環氧化合物中之市售者，例如可列舉：jER828EL、jER1004（皆為三菱化學公司製造）、EPICLON EXA-850CRP（DIC公司製造）等。 作為上述雙酚F型環氧化合物中之市售者，例如可列舉：jER806、jER4004（皆為三菱化學公司製造）等。 作為上述雙酚S型環氧化合物中之市售者，例如可列舉：EPICLON EXA1514（DIC公司製造）等。 作為上述2,2'-二烯丙基雙酚A型環氧化合物中之市售者，例如可列舉：RE-810NM（日本化藥公司製造）等。 作為上述氫化雙酚型環氧化合物中之市售者，例如可列舉：EPICLON EXA7015（DIC公司製造）等。 作為上述環氧丙烷加成雙酚A型環氧化合物中之市售者，例如可列舉：EP-4000S（ADEKA公司製造）等。 作為上述間苯二酚型環氧化合物中之市售者，例如可列舉：EX-201（Nagase ChemteX公司製造）等。 作為上述聯苯型環氧化合物中之市售者，例如可列舉：jER YX-4000H（三菱化學公司製造）等。 作為上述硫醚型環氧化合物中之市售者，例如可列舉：YSLV-50TE（Nippon Steel Chemical & Material Co., Ltd.製造）等。 作為上述二苯醚型環氧化合物中之市售者，例如可列舉：YSLV-80DE（Nippon Steel Chemical & Material Co., Ltd.製造）等。 作為上述二環戊二烯型環氧化合物中之市售者，例如可列舉：EP-4088S（ADEKA公司製造）等。 作為上述萘型環氧化合物中之市售者，例如可列舉：EPICLON HP4032、EPICLON EXA-4700（皆為DIC公司製造）等。 作為上述酚系酚醛清漆型環氧化合物中之市售者，例如可列舉：EPICLON N-770（DIC公司製造）等。 作為上述鄰甲酚酚醛清漆型環氧化合物中之市售者，例如可列舉：EPICLON N-670-EXP-S（DIC公司製造）等。 作為上述二環戊二烯酚醛清漆型環氧化合物中之市售者，例如可列舉：EPICLON HP7200（DIC公司製造）等。 作為上述聯苯酚醛清漆型環氧化合物中之市售者，例如可列舉：NC-3000P（日本化藥公司製造）等。 作為上述萘酚酚醛清漆型環氧化合物中之市售者，例如可列舉：ESN-165S（Nippon Steel Chemical & Material Co., Ltd.製造）等。 作為上述環氧丙胺型環氧化合物中之市售者，例如可列舉：jER630（三菱化學公司製造）、EPICLON 430（DIC公司製造）、TETRAD-X（三菱瓦斯化學公司製造）等。 作為上述烷基多元醇型環氧化合物中之市售者，例如可列舉：ZX-1542（Nippon Steel Chemical & Material Co., Ltd.製造）、EPICLON 726（DIC公司製造）、Epolight 80MFA（共榮社化學公司製造）、Denacol EX-611（Nagase ChemteX公司製造）等。 作為上述橡膠改質型環氧化合物中之市售者，例如可列舉：YR-450、YR-207（皆為Nippon Steel Chemical & Material Co., Ltd.製造）、Epolead PB（DAICEL公司製造）等。 作為上述環氧丙酯化合物中之市售者，例如可列舉：Denacol EX-147（Nagase ChemteX公司製造）等。 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（皆為Nippon Steel Chemical & Material Co., Ltd.製造）、XAC4151（旭化成公司製造）、jER1031、jER1032（皆為三菱化學公司製造）、EXA-7120（DIC公司製造）、TEPIC（日產化學公司製造）等。Examples of commercially available bisphenol A epoxy compounds include jER828EL, jER1004 (both manufactured by Mitsubishi Chemical), and EPICLON EXA-850CRP (manufactured by DIC). Examples of commercially available bisphenol F epoxy compounds include jER806 and jER4004 (both manufactured by Mitsubishi Chemical). Examples of commercially available bisphenol S epoxy compounds include EPICLON EXA1514 (manufactured by DIC). Examples of commercially available 2,2'-diallylbisphenol A epoxy compounds include RE-810NM (manufactured by Nippon Kayaku). Examples of commercially available products of the above-mentioned hydrogenated bisphenol type epoxy compounds include: EPICLON EXA7015 (manufactured by DIC Corporation). Examples of commercially available products of the above-mentioned propylene oxide-added bisphenol A type epoxy compounds include: EP-4000S (manufactured by ADEKA Corporation). Examples of commercially available products of the above-mentioned resorcinol type epoxy compounds include: EX-201 (manufactured by Nagase ChemteX Corporation). Examples of commercially available products of the above-mentioned biphenyl type epoxy compounds include: jER YX-4000H (manufactured by Mitsubishi Chemical Corporation). Examples of commercially available sulfide-type epoxy compounds include YSLV-50TE (manufactured by Nippon Steel Chemical & Material Co., Ltd.). Examples of commercially available diphenyl ether-type epoxy compounds include YSLV-80DE (manufactured by Nippon Steel Chemical & Material Co., Ltd.). Examples of commercially available dicyclopentadiene-type epoxy compounds include EP-4088S (manufactured by ADEKA). Examples of commercially available naphthalene-type epoxy compounds include EPICLON HP4032 and EPICLON EXA-4700 (both manufactured by DIC). Examples of commercially available phenol novolac epoxy compounds include EPICLON N-770 (manufactured by DIC Corporation). Examples of commercially available o-cresol novolac epoxy compounds include EPICLON N-670-EXP-S (manufactured by DIC Corporation). Examples of commercially available dicyclopentadiene novolac epoxy compounds include EPICLON HP7200 (manufactured by DIC Corporation). Examples of commercially available biphenyl novolac epoxy compounds include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.). Examples of commercially available naphthol novolac epoxy compounds include ESN-165S (manufactured by Nippon Steel Chemical & Material Co., Ltd.). Examples of commercially available epoxy compounds include jER630 (manufactured by Mitsubishi Chemical), EPICLON 430 (manufactured by DIC), and TETRAD-X (manufactured by Mitsubishi Gas Chemical). Examples of commercially available alkyl polyol epoxy compounds include ZX-1542 (manufactured by Nippon Steel Chemical & Material Co., Ltd.), EPICLON 726 (manufactured by DIC), Epolight 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), and Denacol EX-611 (manufactured by Nagase ChemteX). Examples of the commercially available rubber-modified epoxy compounds include YR-450, YR-207 (both manufactured by Nippon Steel Chemical & Material Co., Ltd.), Epolead PB (manufactured by DAICEL), etc. Examples of the commercially available glycidyl compounds include Denacol EX-147 (manufactured by Nagase ChemteX), etc. Other commercially available epoxy compounds include, for example, YDC-1312, YSLV-80XY, and YSLV-90CR (all manufactured by Nippon Steel Chemical & Material Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Corporation), jER1031 and jER1032 (all manufactured by Mitsubishi Chemical Corporation), EXA-7120 (manufactured by DIC Corporation), and TEPIC (manufactured by Nissan Chemical Corporation).
作為上述部分(甲基)丙烯酸改質環氧化合物中之市售者，例如可列舉：UVACURE1561、KRM8287（皆為DAICEL-ALLNEX公司製造）、MEM-5000H（Neo Chemical公司製造）等。Examples of the commercially available (meth)acrylic acid-modified epoxy compounds include UVACURE1561, KRM8287 (both manufactured by DAICEL-ALLNEX), and MEM-5000H (manufactured by Neo Chemical).
作為上述環氧(甲基)丙烯酸酯，例如可列舉：藉由按照常規方法使環氧化合物與(甲基)丙烯酸於鹼性觸媒之存在下發生反應而獲得者等。 作為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，可列舉與成為用以合成上述部分(甲基)丙烯酸改質環氧化合物之原料之環氧化合物相同者。Examples of the epoxy (meth)acrylate include those obtained by reacting an epoxy compound with (meth)acrylic acid in the presence of an alkaline catalyst according to a conventional method. As the epoxy compound used as a raw material for synthesizing the epoxy (meth)acrylate, the same epoxy compound used as a raw material for synthesizing the partially (meth)acrylic acid-modified epoxy compound can be cited.
作為上述環氧(甲基)丙烯酸酯中之市售者，例如可列舉：DAICEL-ALLNEX公司製造之環氧(甲基)丙烯酸酯、新中村化學工業公司製造之環氧(甲基)丙烯酸酯、共榮社化學公司製造之環氧(甲基)丙烯酸酯、Nagase ChemteX公司製造之環氧(甲基)丙烯酸酯等。 作為上述DAICEL-ALLNEX公司製造之環氧(甲基)丙烯酸酯，例如可列舉：EBECRYL860、EBECRYL3200、EBECRYL3201、EBECRYL3412、EBECRYL3600、EBECRYL3700、EBECRYL3701、EBECRYL3702、EBECRYL3703、EBECRYL3708、EBECRYL3800、EBECRYL6040、EBECRYL RDX63182等。 作為上述新中村化學工業公司製造之環氧(甲基)丙烯酸酯，例如可列舉：EA-1010、EA-1020、EA-5323、EA-5520、EA-CHD、EMA-1020等。 作為上述共榮社化學公司製造之環氧(甲基)丙烯酸酯，例如可列舉：EPOXYESTER M-600A、EPOXYESTER 40EM、EPOXYESTER 70PA、EPOXYESTER 200PA、EPOXYESTER 80MFA、EPOXYESTER 3002M、EPOXYESTER 3002A、EPOXYESTER 1600A、EPOXYESTER 3000M、EPOXYESTER 3000A、EPOXYESTER 200EA、EPOXYESTER 400EA等。 作為上述Nagase ChemteX公司製造之環氧(甲基)丙烯酸酯，例如可列舉：Denacol Acrylate DA-141、Denacol Acrylate DA-314、Denacol Acrylate DA-911等。Examples of commercially available epoxy (meth)acrylates include epoxy (meth)acrylate manufactured by DAICEL-ALLNEX, epoxy (meth)acrylate manufactured by Shin-Nakamura Chemical Industry, epoxy (meth)acrylate manufactured by Kyoeisha Chemical, and epoxy (meth)acrylate manufactured by Nagase ChemteX. Examples of epoxy (meth) acrylates manufactured by the above-mentioned DAICEL-ALLNEX include EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3708, EBECRYL3800, EBECRYL6040, and EBECRYL RDX63182. Examples of epoxy (meth) acrylates manufactured by the above-mentioned Shin-Nakamura Chemical Industry include EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, and EMA-1020. Examples of epoxy (meth) acrylates manufactured by the aforementioned Kyoeisha Chemical Co., Ltd. include EPOXYESTER M-600A, EPOXYESTER 40EM, EPOXYESTER 70PA, EPOXYESTER 200PA, EPOXYESTER 80MFA, EPOXYESTER 3002M, EPOXYESTER 3002A, EPOXYESTER 1600A, EPOXYESTER 3000M, EPOXYESTER 3000A, EPOXYESTER 200EA, EPOXYESTER 400EA, etc. Examples of epoxy (meth) acrylates manufactured by the aforementioned Nagase ChemteX Co., Ltd. include Denacol Acrylate DA-141, Denacol Acrylate DA-314, Denacol Acrylate DA-911, 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、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)丙烯酸二甲胺基乙酯、(甲基)丙烯酸二乙胺基乙酯、琥珀酸2-(甲基)丙烯醯氧基乙酯、六氫鄰苯二甲酸2-(甲基)丙烯醯氧基乙酯、鄰苯二甲酸2-(甲基)丙烯醯氧基乙基2-羥基丙酯、磷酸2-(甲基)丙烯醯氧基乙酯、(甲基)丙烯酸環氧丙酯等。Examples of the monofunctional (meth)acrylate compounds include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, isodecyl (meth)acrylate, and 2-ethylhexyl (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, isoborneol (meth)acrylate, dicyclopentenyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxy (meth)acrylate, 2-Butoxyethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, methoxyethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, ethyl carbitol (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrahydrofurfuryl (meth)acrylate Fluoropropyl ester, 1H,1H,5H-octafluoropentyl (meth)acrylate, imide (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, 2-(meth)acryloyloxyethyl succinate, 2-(meth)acryloyloxyethyl hexahydrophthalate, 2-(meth)acryloyloxyethyl 2-hydroxypropyl phthalate, 2-(meth)acryloyloxyethyl phosphate, glycidyl (meth)acrylate, etc.
又，作為上述(甲基)丙烯酸酯化合物中之2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、二羥甲基二環戊二烯二(甲基)丙烯酸酯、環氧乙烷改質異三聚氰酸二(甲基)丙烯酸酯、(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 (meth)acrylate compounds include 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, 2-n-butyl-2-ethyl-1,3-propanediol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, Polypropylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, ethylene oxide added bisphenol A di(meth)acrylate, propylene oxide added bisphenol A di(meth)acrylate, ethylene oxide added bisphenol F di(meth)acrylate, dihydroxymethyl dicyclopentadiene di(meth)acrylate, ethylene oxide modified isocyanuric acid di(meth)acrylate, (meth)acrylate 2-hydroxy-3-(meth)acryloyloxypropyl, carbonate diol di(meth)acrylate, polyether diol di(meth)acrylate, polyester diol di(meth)acrylate, polycaprolactone diol di(meth)acrylate, polybutadiene 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、環氧丙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、己內酯改質三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成異三聚氰酸三(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯、環氧丙烷加成甘油三(甲基)丙烯酸酯、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 trifunctional or higher-functional (meth)acrylate compounds include trihydroxymethylpropane tri(meth)acrylate, ethylene oxide-added trihydroxymethylpropane tri(meth)acrylate, propylene oxide-added trihydroxymethylpropane tri(meth)acrylate, caprolactone-modified trihydroxymethylpropane tri(meth)acrylate, ethylene oxide-added isocyanuric acid tri(meth)acrylate, glycerol tri(meth)acrylate, propylene oxide-added glycerol tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tri(meth)acryloyloxyethyl phosphate, di-trihydroxymethylpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and the like.
上述(甲基)丙烯酸胺酯例如可藉由使具有羥基之(甲基)丙烯酸衍生物於觸媒量之錫系化合物存在下對多官能異氰酸酯化合物發生反應而獲得。The (meth) acrylate amine ester can be obtained, for example, by reacting a (meth) acrylic acid derivative having a hydroxyl group with a polyfunctional isocyanate compound in the presence of a catalytic amount of a tin-based compound.
作為上述多官能異氰酸酯化合物，例如可列舉：異佛爾酮二異氰酸酯、2,4-二異氰酸甲苯酯、2,6-二異氰酸甲苯酯、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、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、三苯甲烷三異氰酸酯、硫代磷酸三(異氰酸基苯基)酯、四甲基苯二甲基二異氰酸酯、1,6,11-十一烷三異氰酸酯等。Examples of the polyfunctional isocyanate compound include isophorone diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysamine diisocyanate, triphenylmethane triisocyanate, tris(isocyanatophenyl)phosphorothioate, tetramethylxylylene diisocyanate, and 1,6,11-undecane triisocyanate.
又，作為上述多官能異氰酸酯化合物，亦可使用藉由多元醇與過量之多官能異氰酸酯化合物之反應所獲得之經擴鏈之多官能異氰酸酯化合物。 作為上述多元醇，例如可列舉：乙二醇、丙二醇、甘油、山梨醇、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。Furthermore, as the above-mentioned polyfunctional isocyanate compound, an expanded polyfunctional isocyanate compound obtained by reacting a polyol with an excess of a polyfunctional isocyanate compound can also be used. As the above-mentioned polyol, for example, ethylene glycol, propylene glycol, glycerin, sorbitol, trihydroxymethylpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol, etc. can be listed.
作為上述具有羥基之(甲基)丙烯酸衍生物，例如可列舉：單(甲基)丙烯酸羥基烷基酯、二元醇之單(甲基)丙烯酸酯、三元醇之單(甲基)丙烯酸酯或二(甲基)丙烯酸酯、環氧(甲基)丙烯酸酯等。 作為上述單(甲基)丙烯酸羥基烷基酯，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。 作為上述二元醇，例如可列舉：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。 作為上述三元醇，例如可列舉：三羥甲基乙烷、三羥甲基丙烷、甘油等。 作為上述環氧(甲基)丙烯酸酯，例如可列舉：雙酚A型環氧丙烯酸酯等。Examples of the (meth)acrylic acid derivatives having a hydroxyl group include: hydroxyalkyl mono(meth)acrylate, mono(meth)acrylate of a diol, mono(meth)acrylate or di(meth)acrylate of a triol, epoxy(meth)acrylate, etc. Examples of the hydroxyalkyl mono(meth)acrylate include: 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, etc. Examples of the diols include: ethylene glycol, propylene glycol, 1,3-propylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, polyethylene glycol, etc. Examples of the triols include: trihydroxymethylethane, trihydroxymethylpropane, glycerol, etc. Examples of the epoxy (meth)acrylate include bisphenol A type epoxy acrylate and the like.
作為上述(甲基)丙烯酸胺酯中之市售者，例如可列舉：東亞合成公司製造之(甲基)丙烯酸胺酯、DAICEL-ALLNEX公司製造之(甲基)丙烯酸胺酯、根上工業公司製造之(甲基)丙烯酸胺酯、新中村化學工業公司製造之(甲基)丙烯酸胺酯、共榮社化學公司製造之(甲基)丙烯酸胺酯等。 作為上述東亞合成公司製造之(甲基)丙烯酸胺酯，例如可列舉：M-1100、M-1200、M-1210、M-1600等。 作為上述DAICEL-ALLNEX公司製造之(甲基)丙烯酸胺酯，例如可列舉：EBECRYL210、EBECRYL220、EBECRYL230、EBECRYL270、EBECRYL1290、EBECRYL2220、EBECRYL4827、EBECRYL4842、EBECRYL4858、EBECRYL5129、EBECRYL6700、EBECRYL8402、EBECRYL8803、EBECRYL8804、EBECRYL8807、EBECRYL9260等。 作為上述根上工業公司製造之(甲基)丙烯酸胺酯，例如可列舉：Artresin UN-330、Artresin SH-500B、Artresin UN-1200TPK、Artresin UN-1255、Artresin UN-3320HB、Artresin UN-7100、Artresin UN-9000A、Artresin UN-9000H等。 作為上述新中村化學工業公司製造之(甲基)丙烯酸胺酯，例如可列舉：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等。 作為上述共榮社化學公司製造之(甲基)丙烯酸胺酯，例如可列舉：AH-600、AI-600、AT-600、UA-101I、UA-101T、UA-306H、UA-306I、UA-306T等。Examples of the commercially available (meth)acrylic amine esters include: (meth)acrylic amine esters manufactured by Toagosei Co., Ltd., (meth)acrylic amine esters manufactured by DAICEL-ALLNEX Co., Ltd., (meth)acrylic amine esters manufactured by Negami Kogyo Co., Ltd., (meth)acrylic amine esters manufactured by Shin-Nakamura Chemical Co., Ltd., and (meth)acrylic amine esters manufactured by Kyoeisha Chemical Co., Ltd. Examples of the (meth)acrylic amine esters manufactured by Toagosei Co., Ltd. include: M-1100, M-1200, M-1210, M-1600, etc. Examples of (meth)acrylic amines manufactured by the above-mentioned DAICEL-ALLNEX company include EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270, EBECRYL1290, EBECRYL2220, EBECRYL4827, EBECRYL4842, EBECRYL4858, EBECRYL5129, EBECRYL6700, EBECRYL8402, EBECRYL8803, EBECRYL8804, EBECRYL8807, EBECRYL9260, etc. Examples of (meth)acrylic amines manufactured by the aforementioned Negami Industries include Artresin UN-330, Artresin SH-500B, Artresin UN-1200TPK, Artresin UN-1255, Artresin UN-3320HB, Artresin UN-7100, Artresin UN-9000A, Artresin UN-9000H, etc. Examples of (meth)acrylic amine esters manufactured by the aforementioned Shin-Nakamura Chemical Industry Co., Ltd. include: 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, etc. Examples of the (meth)acrylic amine esters manufactured by the aforementioned Kyoeisha Chemical Co., Ltd. include AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, and UA-306T.
上述硬化性樹脂亦可為了提高所獲得之元件用密封劑之接著性等而含有環氧化合物。作為上述環氧化合物，例如可列舉與成為用以合成上述部分(甲基)丙烯酸改質環氧化合物之原料之環氧化合物相同者。The curable resin may contain an epoxy compound in order to improve the adhesion of the obtained device sealant. Examples of the epoxy compound include the same epoxy compound as the raw material for synthesizing the partially (meth)acrylic acid-modified epoxy compound.
於上述硬化性樹脂含有上述具有(甲基)丙烯醯基之化合物及上述環氧化合物之情形時，較佳為將上述硬化性樹脂中之(甲基)丙烯醯基與環氧基之合計中之(甲基)丙烯醯基之含有比率設為50莫耳%以上且95莫耳%以下。When the curable resin contains the compound having a (meth)acryl group and the epoxy compound, the content ratio of the (meth)acryl group in the total of the (meth)acryl group and the epoxy group in the curable resin is preferably set to 50 mol% or more and 95 mol% or less.
本發明之顯示元件用密封劑含有聚合起始劑及/或熱硬化劑。 作為上述聚合起始劑，例如可列舉：自由基聚合起始劑、陽離子聚合起始劑等。The sealant for display element of the present invention contains a polymerization initiator and/or a thermosetting agent. Examples of the above-mentioned polymerization initiator include free radical polymerization initiators, cationic polymerization initiators, etc.
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、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 a photoradical polymerization initiator that generates radicals by light irradiation and a thermal radical polymerization initiator that generates radicals by heating.
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 系化合物等。 作為上述光自由基聚合起始劑，具體而言，例如可列舉：1-羥基環己基苯基酮、2-苄基-2-二甲胺基-1-(4-味啉基苯基)-1-丁酮、2-(二甲胺基)-2-((4-甲基苯基)甲基)-1-(4-(4-味啉基)苯基)-1-丁酮、2,2-二甲氧基-1,2-二苯乙烷-1-酮、雙(2,4,6-三甲基苯甲醯基)苯基氧化膦、2-甲基-1-(4-甲硫基苯基)-2-味啉基丙基-1-酮、1-(4-(2-羥基乙氧基)-苯基)-2-羥基-2-甲基-1-丙烷-1-酮、1-(4-(苯硫基)苯基)-1,2-辛二酮2-(O-苯甲醯基肟)、2,4,6-三甲基苯甲醯基二苯基氧化膦、安息香甲醚、安息香乙醚、安息香異丙醚等。Examples of the photoradical polymerization initiator include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titaniumocene compounds, oxime ester compounds, benzoin ether compounds, 9-oxysulfur compounds, As the above-mentioned photoradical polymerization initiator, specifically, for example, there can be listed: 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1-(4-furanylphenyl)-1-butanone, 2-(dimethylamino)-2-((4-methylphenyl)methyl)-1-(4-(4-furanyl)phenyl)-1-butanone, 2,2-dimethoxy-1,2-diphenylethane-1-one, bis(2,4,6-trimethylbenzyl)-1-one, )phenylphosphine oxide, 2-methyl-1-(4-methylthiophenyl)-2-furinylpropyl-1-one, 1-(4-(2-hydroxyethoxy)-phenyl)-2-hydroxy-2-methyl-1-propane-1-one, 1-(4-(phenylthio)phenyl)-1,2-octanedione 2-(O-benzoyl oxime), 2,4,6-trimethylbenzyldiphenylphosphine oxide, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, 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所構成之高分子偶氮起始劑。 再者，於本說明書中，所謂高分子偶氮化合物，意指具有偶氮基且藉由熱生成可使(甲基)丙烯醯氧基硬化之自由基、數量平均分子量為300以上之化合物。As the above-mentioned thermal free radical polymerization initiator, for example, those composed of azo compounds, organic peroxides, etc. can be listed. Among them, the polymer azo initiator composed of a polymer azo compound is preferred. Furthermore, in this specification, the so-called polymer azo compound means a compound having an azo group and generating free radicals that can cure (meth)acryloyloxy groups by heat, and having a number average molecular weight of 300 or more.
上述高分子偶氮化合物之數量平均分子量之較佳之下限為1000，較佳之上限為30萬。藉由上述高分子偶氮化合物之數量平均分子量為該範圍，可容易地混合於硬化性樹脂中，於將所獲得之顯示元件用密封劑用於液晶顯示元件之情形時，能夠防止對液晶產生不良影響。上述高分子偶氮化合物之數量平均分子量之更佳之下限為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。 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），使用四氫呋喃作為溶劑來進行測定，並藉由聚苯乙烯換算所求出之值。作為藉由GPC測定利用聚苯乙烯換算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。The preferred lower limit of the number average molecular weight of the above-mentioned high molecular azo compound is 1000, and the preferred upper limit is 300,000. By having the number average molecular weight of the above-mentioned high molecular azo compound in this range, it can be easily mixed in the curable resin, and when the obtained display element sealant is used in a liquid crystal display element, it can prevent adverse effects on the liquid crystal. The preferred lower limit of the number average molecular weight of the above-mentioned high molecular azo compound is 5000, and the preferred upper limit is 100,000, and the further preferred lower limit is 10,000, and the further preferred upper limit is 90,000. Furthermore, in this specification, the above-mentioned number average molecular weight is measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent, and the value is obtained by polystyrene conversion. Examples of columns used when measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko K.K.).
作為上述高分子偶氮化合物，例如可列舉：具有複數個聚環氧烷或聚二甲基矽氧烷等單元經由偶氮基鍵結而成之結構者。 作為具有上述複數個聚環氧烷等單元經由偶氮基鍵結而成之結構之高分子偶氮化合物，較佳為具有聚環氧乙烷結構者。 作為上述高分子偶氮化合物，具體而言，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。 作為上述高分子偶氮化合物中之市售者，例如可列舉：VPE-0201、VPE-0401、VPE-0601、VPS-0501、VPS-1001（皆為FUJIFILM Wako Pure Chemical公司製造）等。 又，關於作為非高分子之偶氮化合物所市售者，例如可列舉：V-65、V-501（皆為FUJIFILM Wako Pure Chemical公司製造）等。Examples of the polymer azo compound include those having a structure in which a plurality of units such as polyoxyalkylene or polydimethylsiloxane are bonded via an azo group. As the polymer azo compound having a structure in which a plurality of units such as polyoxyalkylene are bonded via an azo group, preferably one having a polyethylene oxide structure. As the polymer azo compound, specifically, examples of the polymer azo compound include: a condensate of 4,4'-azobis(4-cyanovaleric acid) and polyalkylene glycol, or a condensate of 4,4'-azobis(4-cyanovaleric acid) and polydimethylsiloxane having a terminal amino group. Examples of the commercially available polymer azo compounds include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (all manufactured by FUJIFILM Wako Pure Chemical Co., Ltd.). In addition, examples of the commercially available non-polymer azo compounds include V-65 and V-501 (all manufactured by FUJIFILM Wako Pure Chemical Co., Ltd.).
作為上述有機過氧化物，例如可列舉：酮過氧化物、過氧縮酮、氫過氧化物、二烷基過氧化物、過氧酯、二乙醯過氧化物、過氧化二碳酸酯等。Examples of the organic peroxide include ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, peroxyester, diacetyl peroxide, and peroxydicarbonate.
作為上述陽離子聚合起始劑，可良好地使用光陽離子聚合起始劑。上述光陽離子聚合起始劑只要為藉由光照射產生質子酸或路易斯酸者，則無特別限定，可為離子性光酸產生類型者，亦可為非離子性光酸產生類型。 作為上述光陽離子聚合起始劑，例如可列舉：芳香族重氮鎓鹽、芳香族鹵鎓鹽、芳香族鋶鹽等鎓鹽類；鐵-芳烴錯合物、二茂鈦錯合物、芳基矽醇-鋁錯合物等有機金屬錯合物類等。As the above-mentioned cationic polymerization initiator, a photo-cationic polymerization initiator can be preferably used. The above-mentioned photo-cationic polymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by light irradiation, and can be an ionic photoacid generating type or a non-ionic photoacid generating type. As the above-mentioned photo-cationic polymerization initiator, for example, onium salts such as aromatic diazonium salts, aromatic halogen onium salts, and aromatic stibnium salts; organic metal complexes such as iron-arene complexes, titanocene complexes, and arylsilanol-aluminum complexes, etc. can be listed.
作為上述光陽離子聚合起始劑中之市售者，例如可列舉：Adeka Optomer SP-150、Adeka Optomer SP-170（皆為ADEKA公司製造）等。Examples of commercially available photocatalytic polymerization initiators include Adeka Optomer SP-150 and Adeka Optomer SP-170 (both manufactured by ADEKA Corporation).
上述聚合起始劑可單獨使用，亦可組合2種以上使用。The above-mentioned polymerization initiators may be used alone or in combination of two or more.
關於上述聚合起始劑之含量，相對於上述硬化性樹脂100重量份，較佳之下限為0.1重量份，較佳之上限為30重量份。藉由上述聚合起始劑之含量為0.1重量份以上，所獲得之顯示元件用密封劑成為硬化性更優異者。藉由上述聚合起始劑之含量為30重量份以下，所獲得之顯示元件用密封劑成為保存穩定性更優異者。上述聚合起始劑之含量之更佳之下限為1重量份，更佳之上限為10重量份，進而較佳之上限為5重量份。Regarding the content of the above-mentioned polymerization initiator, the preferred lower limit is 0.1 parts by weight, and the preferred upper limit is 30 parts by weight relative to 100 parts by weight of the above-mentioned curable resin. When the content of the above-mentioned polymerization initiator is 0.1 parts by weight or more, the obtained sealant for display elements has better curability. When the content of the above-mentioned polymerization initiator is 30 parts by weight or less, the obtained sealant for display elements has better storage stability. The preferred lower limit of the content of the above-mentioned polymerization initiator is 1 part by weight, the preferred upper limit is 10 parts by weight, and the further preferred 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，可良好地使用固形有機酸醯肼。 上述熱硬化劑可單獨使用，亦可組合2種以上使用。Examples of the above-mentioned thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyphenol compounds, acid anhydrides, etc. Among them, solid organic acid hydrazides can be preferably used. The above-mentioned thermosetting agents can be used alone or in combination of two or more.
作為上述固形有機酸醯肼，例如可列舉：1,3-雙(肼基羰乙基)-5-異丙基乙內醯脲、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。 作為上述有機酸醯肼中之市售者，例如可列舉：大塚化學公司製造之有機酸醯肼、Japan FineChem公司製造之有機酸醯肼、Ajinomoto Fine-Techno公司製造之有機酸醯肼等。 作為上述大塚化學公司製造之有機酸醯肼，例如可列舉：SDH、ADH等。 作為上述Japan FineChem公司製造之有機酸醯肼，例如可列舉：MDH等。 作為上述Ajinomoto Fine-Techno公司製造之有機酸醯肼，例如可列舉：Amicure VDH、Amicure VDH-J、Amicure UDH等。Examples of the solid organic acid hydrazides include 1,3-bis(hydrazinocarbonylethyl)-5-isopropylhydantoin, sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, etc. Examples of commercially available organic acid hydrazides include organic acid hydrazides manufactured by Otsuka Chemical Co., Ltd., organic acid hydrazides manufactured by Japan FineChem Co., Ltd., and organic acid hydrazides manufactured by Ajinomoto Fine-Techno Co., Ltd. Examples of organic acid hydrazides manufactured by Otsuka Chemical Co., Ltd. include SDH, ADH, etc. Examples of organic acid hydrazides manufactured by Japan FineChem Co., Ltd. include MDH, etc. Examples of the organic acid hydrazide manufactured by the aforementioned Ajinomoto Fine-Techno Company include Amicure VDH, Amicure VDH-J, and Amicure UDH.
關於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。藉由上述熱硬化劑之含量為1重量份以上，所獲得之顯示元件用密封劑成為熱硬化性更優異者。藉由上述熱硬化劑之含量為50重量份以下，所獲得之顯示元件用密封劑成為塗佈性及保存穩定性更優異者。上述熱硬化劑之含量之更佳之上限為30重量份。Regarding the content of the above-mentioned thermosetting agent, the preferred lower limit is 1 part by weight and the preferred upper limit is 50 parts by weight relative to 100 parts by weight of the above-mentioned curable resin. When the content of the above-mentioned thermosetting agent is 1 part by weight or more, the obtained sealant for display elements becomes one with better thermosetting properties. When the content of the above-mentioned thermosetting agent is 50 parts by weight or less, the obtained sealant for display elements becomes one with better coating properties and storage stability. The more preferred upper limit of the content of the above-mentioned thermosetting agent is 30 parts by weight.
本發明之顯示元件用密封劑較佳為以調整黏度、提高藉由應力分散效果之接著性、改善線膨脹率、提高硬化物之耐濕性等為目的而含有填充劑。The sealant for display devices of the present invention preferably contains a filler for the purpose of adjusting viscosity, improving adhesion by stress dispersion effect, improving linear expansion rate, improving moisture resistance of cured product, etc.
作為上述填充劑，可使用無機填充劑或有機填充劑。 作為上述無機填充劑，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。 作為上述有機填充劑，例如可列舉：聚酯微粒子、聚胺酯（polyurethane）微粒子、乙烯系聚合物微粒子、丙烯酸系聚合物微粒子等。As the above-mentioned filler, an inorganic filler or an organic filler can be used. As the above-mentioned inorganic filler, for example, there can be listed: silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, bentonite, bentonite, montmorillonite, sericite, activated clay, aluminum oxide, 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, etc. As the above-mentioned organic filler, for example, there can be listed: polyester microparticles, polyurethane microparticles, vinyl polymer microparticles, acrylic polymer microparticles, etc.
本發明之顯示元件用密封劑100重量份中之上述填充劑之含量之較佳之下限為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，能夠抑制塗佈性等變差，並且進一步發揮提高接著性等效果。上述填充劑之含量之更佳之下限為20重量份，更佳之上限為60重量份。The preferred lower limit of the content of the filler in 100 parts by weight of the sealant for display elements of the present invention is 10 parts by weight, and the preferred upper limit is 70 parts by weight. By the content of the filler being within this range, the deterioration of the coating property and the like can be suppressed, and the effect of improving the adhesion and the like can be further exerted. The preferred lower limit of the content of the filler is 20 parts by weight, and the preferred upper limit is 60 parts by weight.
本發明之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於將密封劑與基板等良好地進行接著之接著助劑的作用。The sealant for display device of the present invention preferably contains a silane coupling agent. The silane coupling agent mainly serves as a bonding aid for good bonding between the sealant and the substrate.
作為上述矽烷偶合劑，例如可良好地使用3-巰丙基三甲氧基矽烷、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、3-環氧丙氧基丙基三乙氧基矽烷等。該等矽烷偶合劑之提高與基板等之接著性之效果優異，於將所獲得之顯示元件用密封劑用於液晶顯示元件之情形時，能夠抑制硬化性樹脂流出至液晶中。 上述矽烷偶合劑可單獨使用，亦可組合2種以上使用。As the above-mentioned silane coupling agent, for example, 3-butylene trimethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-isocyanate propyl trimethoxysilane, 3-glycidoxypropyl triethoxysilane, etc. can be used well. These silane coupling agents are excellent in improving the adhesion with the substrate, etc., and when the obtained display element sealant is used in a liquid crystal display element, it can inhibit the curable resin from flowing into the liquid crystal. The above-mentioned silane coupling agents can be used alone or in combination of two or more.
本發明之顯示元件用密封劑100重量份中之上述矽烷偶合劑之含量之較佳之下限為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，所獲得之顯示元件用密封劑成為接著性更優異者，於將所獲得之顯示元件用密封劑用於液晶顯示元件之情形時，能夠抑制液晶污染之產生。上述矽烷偶合劑之含量之更佳之下限為0.3重量份，更佳之上限為5重量份。The preferred lower limit of the content of the silane coupling agent in 100 parts by weight of the sealant for display elements of the present invention is 0.1 parts by weight, and the preferred upper limit is 10 parts by weight. When the content of the silane coupling agent is within this range, the sealant for display elements obtained has better adhesion, and when the sealant for display elements obtained is used in liquid crystal display elements, the generation of liquid crystal contamination can be suppressed. The preferred lower limit of the content of the silane coupling agent is 0.3 parts by weight, and the preferred upper limit is 5 parts by weight.
本發明之顯示元件用密封劑亦可含有上述遮光劑。藉由含有上述遮光劑，本發明之顯示元件用密封劑可良好地用作遮光密封劑。The sealant for display element of the present invention may also contain the above-mentioned light-shielding agent. By containing the above-mentioned light-shielding agent, the sealant for display element of the present invention can be used well as a light-shielding sealant.
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。 上述遮光劑可單獨使用，亦可組合2種以上使用。Examples of the above-mentioned sunscreen include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, resin-coated carbon black, etc. Among them, titanium black is preferred. The above-mentioned sunscreens may be used alone or in combination of two or more.
上述鈦黑係對於紫外線區域附近、尤其是波長370 nm以上且450 nm以下之光之透過率與對於波長300 nm以上且800 nm以下之光之平均透過率相比變高之物質。即，上述鈦黑係具有如下性質之遮光劑：一方面藉由充分遮蔽可見光區域之波長之光而對本發明之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。作為本發明之顯示元件用密封劑中所含之遮光劑，較佳為絕緣性較高之物質，鈦黑亦適合作為絕緣性較高之遮光劑。The titanium black is a substance whose transmittance to light near the ultraviolet region, especially light with a wavelength of 370 nm or more and 450 nm or less, is higher than the average transmittance to light with a wavelength of 300 nm or more and 800 nm or less. That is, the titanium black is a light-shielding agent having the following properties: on the one hand, it imparts light-shielding properties to the sealant for the display element of the present invention by fully shielding light with a wavelength in the visible light region, and on the other hand, it allows light with a wavelength near the ultraviolet region to pass through. As a light-shielding agent contained in the sealant for the display element of the present invention, a substance with high insulation is preferred, and titanium black is also suitable as a light-shielding agent with high insulation.
上述鈦黑即使為未經表面處理者，亦發揮充分之效果，但亦可使用表面利用偶合劑等有機成分進行過處理者、或由氧化矽、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，就能夠進一步提高絕緣性之方面而言，較佳為利用有機成分進行過處理者。 又，使用含有上述鈦黑作為遮光劑之本發明之顯示元件用密封劑所製造之顯示元件由於具有充分之遮光性，故而無光之漏出而具有較高之對比度，可實現具有優異之影像顯示品質之顯示元件。The titanium black mentioned above can exert sufficient effect even if it is not surface treated, but titanium black that has been surface treated with organic components such as coupling agents, or covered with inorganic components such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, and magnesium oxide can also be used. Among them, in terms of being able to further improve the insulation, it is better to use a surface treated with an organic component. In addition, the display element manufactured using the sealant for the display element of the present invention containing the above-mentioned titanium black as a light-shielding agent has sufficient light-shielding properties, so there is no light leakage and has a higher contrast, which can realize a display element with excellent image display quality.
作為上述鈦黑中之市售者，例如可列舉：Mitsubishi Materials Corporation製造之鈦黑、赤穗化成公司製造之鈦黑等。 作為上述Mitsubishi Materials Corporation製造之鈦黑，例如可列舉：12S、13M、13M-C、13R-N、14M-C等。 作為上述赤穗化成公司製造之鈦黑，例如可列舉Tilack D等。Examples of the titanium blacks on the market include titanium blacks manufactured by Mitsubishi Materials Corporation and titanium blacks manufactured by Ako Chemical Co., Ltd. Examples of the titanium blacks manufactured by Mitsubishi Materials Corporation include 12S, 13M, 13M-C, 13R-N, and 14M-C. Examples of the titanium blacks manufactured by Ako Chemical Co., Ltd. include Tilack D.
上述鈦黑之比表面積之較佳之下限為13 m2 /g，較佳之上限為30 m2 /g，更佳之下限為15 m2 /g，更佳之上限為25 m2 /g。 又，上述鈦黑之體積電阻之較佳之下限為0.5 Ω・cm，較佳之上限為3 Ω・cm，更佳之下限為1 Ω・cm，更佳之上限為2.5 Ω・cm。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. In addition, the preferred lower limit of the volume resistivity of the titanium black is 0.5 Ω·cm, the preferred upper limit is 3 Ω·cm, the more preferred lower limit is 1 Ω·cm, and the more preferred upper limit is 2.5 Ω·cm.
上述遮光劑之一次粒徑只要為顯示元件之基板間之距離以下，則無特別限定，較佳之下限為1 nm，較佳之上限為5000 nm。藉由上述遮光劑之一次粒徑為該範圍，可在不使所獲得之顯示元件用密封劑之繪圖性等變差之情況下使遮光性更加優異。上述遮光劑之一次粒徑之更佳之下限為5 nm，更佳之上限為200 nm，進而較佳之下限為10 nm，進而較佳之上限為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）中而進行測定。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 display element. The preferred lower limit is 1 nm and the preferred upper limit is 5000 nm. By having the primary particle size of the above-mentioned light-shielding agent within this range, the light-shielding property can be made more excellent without deteriorating the drawing properties of the obtained sealant for display elements. The preferred lower limit of the primary particle size of the above-mentioned light-shielding agent is 5 nm, the preferred upper limit is 200 nm, the further preferred lower limit is 10 nm, and the further preferred upper limit is 100 nm. 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).
本發明之顯示元件用密封劑100重量份中之上述遮光劑之含量之較佳之下限為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，所獲得之顯示元件用密封劑之接著性、硬化後之強度、及一面抑制繪圖性變差一面提高遮光性之效果更加優異。上述遮光劑之含量之更佳之下限為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。The preferred lower limit of the content of the light-shielding agent in 100 parts by weight of the sealant for display elements of the present invention is 5 parts by weight, and the preferred upper limit is 80 parts by weight. When the content of the light-shielding agent is within this range, the sealant for display elements has better adhesion, strength after curing, and the effect of suppressing the deterioration of drawing properties and improving light-shielding properties. The preferred lower limit of the content of the light-shielding agent is 10 parts by weight, and the preferred upper limit is 70 parts by weight, and the further preferred lower limit is 30 parts by weight, and the further preferred upper limit is 60 parts by weight.
本發明之顯示元件用密封劑亦可進而視需要含有反應性稀釋劑、間隔件、硬化促進劑、消泡劑、調平劑、聚合抑制劑、其他偶合劑等添加劑。The sealant for display elements of the present invention may further contain additives such as reactive diluents, spacers, curing accelerators, defoaming agents, leveling agents, polymerization inhibitors, and other coupling agents as needed.
作為製造本發明之顯示元件用密封劑之方法，例如可列舉：使用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進行混合之方法等。 作為上述混合機，例如可列舉：勻相分散機（homo disper）、均質攪拌機（homo mixer）、萬能攪拌機、行星式混合機、捏合機、三輥研磨機等。As a method for manufacturing the sealant for the display element of the present invention, for example, there can be listed: a method of mixing a curable resin, a polymerization initiator and/or a thermosetting agent, and a silane coupling agent added as needed using a mixer, etc. As the above-mentioned mixer, for example, there can be listed: a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, a three-roll grinder, etc.
藉由於本發明之顯示元件用密封劑中摻合導電性微粒子，可製造上下導通材料。此種含有本發明之顯示元件用密封劑及導電性微粒子之上下導通材料亦為本發明之一。By mixing conductive microparticles into the sealant for display elements of the present invention, a vertical conductive material can be manufactured. Such a vertical conductive material containing the sealant for display elements of the present invention and conductive microparticles is also one of the present invention.
上述導電性微粒子並無特別限定，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之優異彈性，可在不損傷透明基板等之情況下實現導電連接，故而較佳。The conductive particles are not particularly limited, and metal spheres, resin particles with a conductive metal layer formed on the surface, etc. can be used. Among them, the conductive metal layer formed on the surface of the resin particles is preferred because the excellent elasticity of the resin particles can achieve conductive connection without damaging the transparent substrate, etc., so it is preferred.
具有本發明之顯示元件用密封劑之硬化物、或本發明之上下導通材料之硬化物之顯示元件亦為本發明之一。作為本發明之顯示元件，較佳為液晶顯示元件。 作為使用本發明之顯示元件用密封劑製造液晶顯示元件之方法，可良好地使用液晶滴下法，具體而言，例如可列舉具有以下各步驟之方法等。 首先，進行如下步驟：藉由網版印刷、點膠機（dispenser）塗佈等將本發明之顯示元件用密封劑塗佈於具有ITO薄膜等電極之2片透明基板中之一片上，而形成框狀之密封圖案。繼而，進行如下步驟：將液晶之微小液滴滴下至密封圖案之框內整面並進行塗佈，於真空下重疊另一片透明基板。其後，進行對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、及對暫時硬化之密封劑進行加熱而使之正式硬化之步驟，藉由此種方法，可獲得液晶顯示元件。 [發明之效果]A display element having a cured product of the sealant for display elements of the present invention or a cured product of the upper and lower conductive material of the present invention is also one of the present invention. As the display element of the present invention, a liquid crystal display element is preferably used. As a method for manufacturing a liquid crystal display element using the sealant for display elements of the present invention, a liquid crystal dropping method can be used well. Specifically, for example, a method having the following steps can be listed. First, the following steps are performed: the sealant for display elements of the present invention is applied to one of two transparent substrates having an electrode such as an ITO film by screen printing, dispensing, etc., to form a frame-shaped sealing pattern. Then, the following steps are performed: tiny droplets of liquid crystal are dripped onto the entire surface of the frame of the sealing pattern and coated, and another transparent substrate is superimposed under vacuum. After that, the sealing pattern portion is irradiated with ultraviolet light or the like to temporarily cure the sealant, and the temporarily cured sealant is heated to formally cure it. By this method, a liquid crystal display element can be obtained. [Effect of the invention]
根據本發明，可提供一種能夠獲得高溫高濕環境下之可靠性優異之顯示元件之顯示元件用密封劑。又，根據本發明，可提供一種使用該顯示元件用密封劑而成之上下導通材料及顯示元件。According to the present invention, a display element sealant can be provided that can obtain a display element with excellent reliability in a high temperature and high humidity environment. In addition, according to the present invention, an upper and lower conductive material and a display element formed by using the display element sealant can be provided.
以下，記載實施例而更加詳細地對本發明進行說明，但本發明並不僅限定於該等實施例。The present invention will be described in more detail below with reference to embodiments, but the present invention is not limited to these embodiments.
（實施例1～5、比較例1～3） 按照表1中所記載之摻合比，使用行星式攪拌機將各材料進行混合後，進而使用三輥研磨機進行混合，藉此製備顯示元件用密封劑。作為上述行星式攪拌機，使用去泡攪拌太郎（Thinky公司製造）。 對於所獲得之各顯示元件用密封劑，使用金屬鹵化物燈照射30秒100 mW/cm2 之紫外線（波長365 nm）後，於120℃加熱1小時，藉此獲得硬化物。 對於所獲得之硬化物，使用動態黏彈性測定裝置，於試驗片寬度5 mm、厚度0.35 mm、抓持寬度25 mm、升溫速度10℃/分鐘、頻率5 Hz之條件下測定動態黏彈性，求出損耗正切（tanδ）之極大值之溫度作為玻璃轉移溫度。作為上述動態黏彈性測定裝置，使用DVA-200（IT計測控制公司製造）。將結果示於表1。 又，對所獲得之硬化物進行於121℃、100%RH、2 atm之環境下暴露48小時之高溫高濕試驗。測定硬化前之顯示元件用密封劑於25℃之比重、及高溫高濕試驗後之硬化物於25℃之比重，利用上述式算出硬化收縮率。將結果示於表1。(Examples 1 to 5, Comparative Examples 1 to 3) After mixing the materials according to the blending ratio listed in Table 1 using a planetary mixer, the materials were further mixed using a three-roll mill to prepare a sealant for display components. As the planetary mixer, a defoaming mixer Taro (manufactured by Thinky Co., Ltd.) was used. Each of the sealants for display components obtained was irradiated with ultraviolet light (wavelength 365 nm) of 100 mW/ cm2 using a metal halide lamp for 30 seconds, and then heated at 120°C for 1 hour to obtain a cured product. The obtained hardened material was measured for dynamic viscoelasticity using a dynamic viscoelasticity measuring device under the conditions of a test piece width of 5 mm, a thickness of 0.35 mm, a gripping width of 25 mm, a heating rate of 10°C/min, and a frequency of 5 Hz, and the temperature at which the maximum value of the loss tangent (tanδ) was obtained was taken as the glass transition temperature. As the above-mentioned dynamic viscoelasticity measuring device, DVA-200 (manufactured by IT Measurement and Control Co., Ltd.) was used. The results are shown in Table 1. In addition, the obtained hardened material was exposed to a high temperature and high humidity test for 48 hours in an environment of 121°C, 100%RH, and 2 atm. The specific gravity of the display element sealant before curing at 25°C and the specific gravity of the cured product after the high temperature and high humidity test at 25°C were measured, and the curing shrinkage rate was calculated using the above formula. The results are shown in Table 1.
＜評價＞ 對實施例及比較例中所獲得之各顯示元件用密封劑進行以下之評價。將結果示於表1。<Evaluation> Each of the sealants for display devices obtained in the embodiments and comparative examples was evaluated as follows. The results are shown in Table 1.
（高溫高濕環境下之可靠性） 於實施例及比較例中所獲得之各顯示元件用密封劑100重量份中均勻地分散間隔件粒子1重量份。作為間隔件粒子，使用Micropearl SI-H050（積水化學工業公司製造）。將分散有間隔件粒子之密封劑填充至點膠用注射器中，進行脫泡處理後，利用點膠機以繪製長方形框之方式塗佈於附有配向膜及ITO薄膜之透明基板上。使用PSY-10E（武藏高科技公司製造）作為注射器，使用SHOTMASTER300（武藏高科技公司製造）作為點膠機。繼而，將液晶之微小液滴滴下至密封劑之框內整面並進行塗佈，立刻貼合另一透明基板。作為液晶，使用JC-5004LA（Chisso公司製造）。剛貼合透明基板後，使用金屬鹵化物燈對密封劑部分照射30秒100 mW/cm2 之紫外線（波長365 nm），其後，於120℃加熱1小時，藉此獲得液晶顯示元件。對於實施例及比較例中所獲得之各顯示元件用密封劑，分別製作20個液晶顯示元件。 將所獲得之液晶顯示元件於PCT條件（121℃、100%RH、2 atm）下暴露48小時。對於在PCT條件下暴露後之液晶顯示元件，藉由目視觀察確認有無氣泡。 將20個液晶顯示元件均未確認到氣泡之情形設為「◎」，將1個以上且3個以下之液晶顯示元件確認到氣泡之情形設為「○」，將4個以上且8個以下之液晶顯示元件確認到氣泡之情形設為「△」，將9個以上之液晶顯示元件確認到氣泡之情形設為「×」，評價高溫高濕環境下之可靠性。(Reliability in a high temperature and high humidity environment) 1 part by weight of spacer particles is uniformly dispersed in 100 parts by weight of the sealant for each display element obtained in the embodiment and the comparative example. Micropearl SI-H050 (manufactured by Sekisui Chemical Industries, Ltd.) is used as the spacer particles. The sealant in which the spacer particles are dispersed is filled into a syringe for dispensing glue, and after degassing, it is applied to a transparent substrate with an alignment film and an ITO film by drawing a rectangular frame using a glue dispenser. PSY-10E (manufactured by Musashi High-Tech Co., Ltd.) is used as a syringe, and SHOTMASTER300 (manufactured by Musashi High-Tech Co., Ltd.) is used as a glue dispenser. Then, tiny droplets of liquid crystal are dripped onto the entire surface of the sealant frame and applied, and another transparent substrate is immediately attached. As liquid crystal, JC-5004LA (manufactured by Chisso Corporation) was used. Immediately after the transparent substrate was bonded, the sealant portion was irradiated with ultraviolet light (wavelength 365 nm) of 100 mW/ cm2 for 30 seconds using a metal halide lamp, and then heated at 120°C for 1 hour to obtain a liquid crystal display element. For each display element obtained in the embodiment and the comparative example, 20 liquid crystal display elements were prepared using the sealant. The obtained liquid crystal display elements were exposed to PCT conditions (121°C, 100% RH, 2 atm) for 48 hours. For the liquid crystal display elements exposed under PCT conditions, the presence or absence of bubbles was confirmed by visual observation. The situation where no bubbles were confirmed in 20 LCD display components was set to "◎", the situation where bubbles were confirmed in more than 1 and less than 3 LCD display components was set to "○", the situation where bubbles were confirmed in more than 4 and less than 8 LCD display components was set to "△", and the situation where bubbles were confirmed in more than 9 LCD display components was set to "×" to evaluate the reliability in a high temperature and high humidity environment.
[表1]
根據本發明，可提供一種能夠獲得高溫高濕環境下之可靠性優異之顯示元件之顯示元件用密封劑。又，根據本發明，可提供一種使用該顯示元件用密封劑而成之上下導通材料及顯示元件。According to the present invention, a display element sealant can be provided that can obtain a display element with excellent reliability in a high temperature and high humidity environment. In addition, according to the present invention, an upper and lower conductive material and a display element formed by using the display element sealant can be provided.
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- 2020-06-29 KR KR1020217029901A patent/KR102780821B1/en active Active
- 2020-06-29 JP JP2020540840A patent/JP6905158B2/en active Active
- 2020-06-29 KR KR1020217030827A patent/KR102719152B1/en active Active
- 2020-06-29 JP JP2020540841A patent/JP6910561B2/en active Active
- 2020-06-29 TW TW109121874A patent/TWI862613B/en active
- 2020-06-29 WO PCT/JP2020/025479 patent/WO2021002317A1/en not_active Ceased
- 2020-06-29 CN CN202080036217.1A patent/CN113826043B/en active Active
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2021
- 2021-06-17 JP JP2021100842A patent/JP2021167416A/en active Pending
- 2021-07-06 JP JP2021112291A patent/JP7602437B2/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| TWI862613B (en) | 2024-11-21 |
| KR102780821B1 (en) | 2025-03-12 |
| KR20220023751A (en) | 2022-03-02 |
| JP7602437B2 (en) | 2024-12-18 |
| JPWO2021002318A1 (en) | 2021-09-13 |
| JP6910561B2 (en) | 2021-07-28 |
| JP2021177246A (en) | 2021-11-11 |
| WO2021002317A1 (en) | 2021-01-07 |
| TW202108694A (en) | 2021-03-01 |
| KR20220027054A (en) | 2022-03-07 |
| TW202108693A (en) | 2021-03-01 |
| WO2021002318A1 (en) | 2021-01-07 |
| CN113924351A (en) | 2022-01-11 |
| CN113826043B (en) | 2024-07-23 |
| JP2021167416A (en) | 2021-10-21 |
| CN113826043A (en) | 2021-12-21 |
| JP6905158B2 (en) | 2021-07-21 |
| JPWO2021002317A1 (en) | 2021-09-13 |
| CN113924351B (en) | 2024-09-03 |
| KR102719152B1 (en) | 2024-10-17 |
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