KR20190077220A - Sealant for display, and liquid crystal display using the same - Google Patents
Sealant for display, and liquid crystal display using the same Download PDFInfo
- Publication number
- KR20190077220A KR20190077220A KR1020180158974A KR20180158974A KR20190077220A KR 20190077220 A KR20190077220 A KR 20190077220A KR 1020180158974 A KR1020180158974 A KR 1020180158974A KR 20180158974 A KR20180158974 A KR 20180158974A KR 20190077220 A KR20190077220 A KR 20190077220A
- Authority
- KR
- South Korea
- Prior art keywords
- display
- component
- meth
- compound
- liquid crystal
- Prior art date
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 36
- 239000000565 sealant Substances 0.000 title abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000000524 functional group Chemical group 0.000 claims abstract description 15
- -1 acrylic compound Chemical class 0.000 claims description 41
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- 239000004593 Epoxy Substances 0.000 claims description 26
- 238000007789 sealing Methods 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000007870 radical polymerization initiator Substances 0.000 claims description 12
- 239000011256 inorganic filler Substances 0.000 claims description 11
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 11
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000012766 organic filler Substances 0.000 claims description 6
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims description 2
- 230000035699 permeability Effects 0.000 abstract description 13
- 239000008393 encapsulating agent Substances 0.000 description 41
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- 239000000758 substrate Substances 0.000 description 19
- 239000003822 epoxy resin Substances 0.000 description 17
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- 238000001723 curing Methods 0.000 description 13
- 239000010419 fine particle Substances 0.000 description 12
- 239000000853 adhesive Substances 0.000 description 11
- 230000001070 adhesive effect Effects 0.000 description 11
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 235000006732 Torreya nucifera Nutrition 0.000 description 4
- 244000111306 Torreya nucifera Species 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229960001755 resorcinol Drugs 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 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 2
- MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 description 2
- OVJHMJJVXOJMBB-UHFFFAOYSA-N 2-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)ethyl prop-2-enoate Chemical compound C1CCCC2C(=O)N(CCOC(=O)C=C)C(=O)C21 OVJHMJJVXOJMBB-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
- QCBSYPYHCJMQGB-UHFFFAOYSA-N 2-ethyl-1,3,5-triazine Chemical compound CCC1=NC=NC=N1 QCBSYPYHCJMQGB-UHFFFAOYSA-N 0.000 description 2
- OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-UHFFFAOYSA-N 0.000 description 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229920000800 acrylic rubber Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
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- 229930003836 cresol Natural products 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 2
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- 229910052618 mica group Inorganic materials 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 235000010292 orthophenyl phenol Nutrition 0.000 description 2
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
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- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
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- 239000010409 thin film Substances 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
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- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
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- ROFVGYAMRSGUSQ-UHFFFAOYSA-N 1-(2-bromoethyl)piperazine;hydrobromide Chemical compound Br.BrCCN1CCNCC1 ROFVGYAMRSGUSQ-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- SKHBJDDIGYYYMJ-UHFFFAOYSA-N 2,6-ditert-butyl-6-methylcyclohexa-1,3-dien-1-ol Chemical compound CC(C)(C)C1=C(O)C(C)(C(C)(C)C)CC=C1 SKHBJDDIGYYYMJ-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
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- YVXZYNDUTBWZLJ-UHFFFAOYSA-N 2-(7-oxabicyclo[4.1.0]heptan-3-yl)-3-trimethoxysilylpropan-1-amine Chemical compound C1(CC2C(CC1)O2)C(C[Si](OC)(OC)OC)CN YVXZYNDUTBWZLJ-UHFFFAOYSA-N 0.000 description 1
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- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
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- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- LGYJSPMYALQHBL-UHFFFAOYSA-N pentanedihydrazide Chemical compound NNC(=O)CCCC(=O)NN LGYJSPMYALQHBL-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
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- 239000002985 plastic film Substances 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
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- 230000008569 process Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
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- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 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
- 229920002050 silicone resin Polymers 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
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J3/00—Processes of treating or compounding macromolecular substances
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- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
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- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
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- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
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- 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
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- 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
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Abstract
Description
본 발명은, 플렉시블 디스플레이나 만곡 형상의 디스플레이에도 적용할 수 있는 디스플레이용 봉지제에 관한 것이다. 보다 상세하게는, 유리 전이 온도와 탄성률에 있어서 특정의 관계를 충족하는 디스플레이용 봉지제에 관한 것이다. 이 디스플레이용 봉지제는, 유연성과 저투습성을 양립할 수 있는 것이기 때문에, 특히 플렉시블 디스플레이나 만곡 형상의 디스플레이용 봉지제로서 유용하다.The present invention relates to a display encapsulant that can be applied to a flexible display or a curved display. More particularly, the present invention relates to a sealing agent for a display which satisfies a specific relationship in glass transition temperature and elastic modulus. This encapsulant for display is useful as a flexible display or a curved display encapsulant, since it can provide both flexibility and low moisture permeability.
또한, 본 발명과 같이 유연성이 풍부한 봉지제는, 피착체와의 접착 강도가 우수하기 때문에, 고접착 강도가 요구되는 용도에 있어서도 유용하다.Further, the sealing agent having a high flexibility as in the present invention is also useful in applications requiring high adhesive strength because of its excellent bonding strength to an adherend.
디스플레이용 봉지제란, 예를 들면 액정 디스플레이용 시일제, 유기 EL 디스플레이용 봉지제나 터치 패널용 접착제 등을 들 수 있다. 이들의 재료로서 공통되어 있는 것은, 우수한 경화성을 가지면서, 아웃 가스가 적고, 표시 소자에 대미지를 주지 않는다는 특성이 요구되는 점이다.Examples of encapsulating agents for displays include sealants for liquid crystal displays, encapsulating agents for organic EL displays, adhesives for touch panels, and the like. What is common to these materials is that they have excellent curability and are required to have little outgas and no damage to the display element.
또한 최근에는, 만곡한 형상의 디스플레이나, 플렉시블성이 풍부한 디스플레이가 개발되어 제품화되고 있다. 이와 같은 디스플레이에 사용되는 기판은, 종래의 유리와 같은 강직한 것 대신에, 플라스틱 필름과 같은 유연한 것이 사용되고 있다(특허문헌 1).In addition, in recent years, a curved display or a flexible display has been developed and commercialized. A flexible substrate such as a plastic film is used as a substrate for such a display instead of a rigid substrate such as a conventional glass (Patent Document 1).
이러한 배경으로부터, 디스플레이용 봉지제에는 기판 등의 휨에 추종하는 바와 같은, 즉 경화 후에 있어서도 유연하다는 성질이 요구되고 있다.From this background, it has been demanded that the encapsulant for display is flexible, such as following a warp of a substrate or the like, that is, even after curing.
또한, 유연성이 우수한 봉지제는, 접착 강도에 있어서도 유리하다. 예를 들면, 충격에 의한 박리나 기재 파괴를 경감할 수 있다. 이 관점에서도, 봉지제에 대한 유연성 부여라는 요구는 높아지고 있다.Further, the sealing agent having excellent flexibility is also advantageous in the adhesive strength. For example, detachment due to impact and base breakage can be reduced. Even from this point of view, there is a growing demand for imparting flexibility to the encapsulant.
한편, 경화물의 유연성을 높이기 위해서는, 경화물의 가교 밀도를 내리는 것이 유효한 수단이다. 그러나, 가교 밀도가 내려가면 투습성을 악화시키는 것이 통상이다. 이는 네트워크의 느슨한 부분으로부터 수분이 침입하기 때문이라고 생각된다. 따라서, 저투습성을 담보하기 위해서는, 가교 밀도를 내리지 않고 유연성을 높이거나, 가교 밀도는 내리지만 투습성을 악화시키지 않는다는 상반되는 특성의 실현이 필요해진다.On the other hand, in order to increase the flexibility of the cured product, it is effective to lower the crosslinking density of the cured product. However, when the crosslinking density is lowered, the moisture permeability is generally deteriorated. This is probably due to the invasion of moisture from loose parts of the network. Therefore, in order to ensure low moisture permeability, it is necessary to realize the opposite property that the flexibility is increased without lowering the crosslinking density or the crosslinking density is lowered but the moisture permeability is not deteriorated.
종래, 접착 강도 향상의 관점에서, 유연성을 갖는 표시 소자용 접착제의 개발이 행해져 왔다(특허문헌 2). 그러나, 상기의 유연한 기판에 적응하기 위한 충분한 성능을 구비한 것은 아직 실현되고 있지 않다.Conventionally, an adhesive for a display device having flexibility has been developed from the viewpoint of improvement in adhesive strength (Patent Document 2). However, it has not yet been realized that there is sufficient performance for adapting to the above flexible substrate.
본 발명은, 플렉시블 디스플레이나 만곡 형상의 디스플레이에도 적용할 수 있는 디스플레이용 봉지제에 관한 것이다. 보다 상세하게는, 3 이상의 반응성 관능기와, 특정의 물성을 갖는 화합물을 이용한 디스플레이용 봉지제에 관한 것이다. 이 디스플레이용 봉지제는, 유연성과 저투습성을 양립할 수 있는 것이기 때문에, 디스플레이용 봉지제로서 유용하다.The present invention relates to a display encapsulant that can be applied to a flexible display or a curved display. More particularly, the present invention relates to a sealing agent for a display using a compound having three or more reactive functional groups and specific physical properties. This encapsulant for display is useful as an encapsulating material for displays because it can achieve both flexibility and low moisture permeability.
본 발명자들은, 예의 검토의 결과, 3 이상의 반응성 관능기와, 특정의 물성을 갖는 화합물을 함유하는 디스플레이용 봉지제가 유연성과 저투습성이 매우 우수한 것을 발견하여, 본 발명에 이른 것이다.As a result of intensive studies, the inventors of the present invention discovered that a display encapsulant containing a compound having three or more reactive functional groups and a specific physical property is very excellent in flexibility and low moisture permeability, and has reached the present invention.
또한, 본 명세서 중, 본 명세서에 있어서 「(메타)아크릴」이란 「아크릴」및/또는 「메타크릴」을 의미한다.In the present specification, " (meth) acrylic " in this specification means " acrylic " and / or " methacrylic ".
즉 본 발명은, 다음의 [1]∼[14]에 관한 것이다.That is, the present invention relates to the following [1] to [14].
[1] 성분 (A): 분자 내에 3 이상의 비스페놀 골격 및, 3 이상의 반응성 관능기를 갖는 경화성 화합물[1] Component (A): A curable compound having three or more bisphenol skeletons and at least three reactive functional groups in a molecule
을 함유하는 디스플레이용 봉지제.≪ / RTI >
[2] 상기 성분 (A)의 비스페놀 골격 내(內) 2 이상이 비스페놀 A 골격인 전항 1에 기재된 디스플레이용 봉지제.[2] The encapsulant for display according to the above 1, wherein at least 2 of the bisphenol skeleton of the component (A) is a bisphenol A skeleton.
[3] 상기 성분 (A)의 중량 평균 분자량이 1000 이상인 전항 1 또는 2에 기재된 디스플레이용 봉지제.[3] The encapsulating material for display according to the above item 1 or 2, wherein the component (A) has a weight average molecular weight of 1000 or more.
[4] 상기 성분 (A)의 반응성 관능기 내 2개 이상이 (메타)아크릴로일기인 전항 1 내지 3 중 어느 한 항에 기재된 디스플레이용 봉지제.[4] The encapsulant for display according to any one of items 1 to 3, wherein at least two of the reactive functional groups of the component (A) are (meth) acryloyl groups.
[5] 추가로, 성분 (B) 경화성 화합물을 함유하는 전항 1 내지 4 중 어느 한 항에 기재된 디스플레이용 봉지제.[5] The encapsulant for display according to any one of items 1 to 4, further comprising a curing compound of component (B).
[6] 상기 성분 (B)가, 성분 (B-1) (메타)아크릴 화합물인 전항 5에 기재된 디스플레이용 봉지제.[6] The encapsulating agent for display according to the above item 5, wherein the component (B) is the component (B-1) (meth) acrylic compound.
[7] 상기 성분 (B)가, 성분 (B-1) (메타)아크릴 화합물과 성분 (B-2) 에폭시 화합물의 혼합물인 전항 5에 기재된 디스플레이용 봉지제.[7] The encapsulating material for display according to the above item 5, wherein the component (B) is a mixture of the component (B-1) the (meth) acrylic compound and the component (B-2) epoxy compound.
[8] 추가로, 성분 (C) 유기 필러를 함유하는 전항 1 내지 7 중 어느 한 항에 기재된 디스플레이용 봉지제.[8] The encapsulant for display according to any one of items 1 to 7, further comprising a component (C) organic filler.
[9] 추가로, 성분 (D) 무기 필러를 함유하는 전항 1 내지 8 중 어느 한 항에 기재된 디스플레이용 봉지제.[9] The encapsulant for display according to any one of items 1 to 8, further comprising an inorganic filler as component (D).
[10] 추가로, 성분 (E) 실란 커플링제를 함유하는 전항 1 내지 9 중 어느 한 항에 기재된 디스플레이용 봉지제.[10] The encapsulant for display according to any one of items 1 to 9, further comprising a component (E) silane coupling agent.
[11] 추가로, 성분 (F) 열 경화제를 함유하는 전항 1 내지 10 중 어느 한 항에 기재된 디스플레이용 봉지제.[11] The encapsulant for display according to any one of items 1 to 10, further comprising a component (F) thermosetting agent.
[12] 추가로, 성분 (G) 광 라디칼 중합 개시제를 함유하는 전항 1 내지 11 중 어느 한 항에 기재된 디스플레이용 봉지제.[12] The encapsulating agent for display according to any one of items 1 to 11, further comprising a component (G) photo radical polymerization initiator.
[13] 추가로, 성분 (H) 열 라디칼 중합 개시제를 함유하는 전항 1 내지 12 중 어느 한 항에 기재된 디스플레이용 봉지제.[13] The encapsulant for display according to any one of items 1 to 12, further comprising a component (H) thermal radical polymerization initiator.
[14] 전항 1 내지 13 중 어느 한 항에 기재된 디스플레이용 봉지제에 의해 봉지된 액정 디스플레이.[14] A liquid crystal display encapsulated by the encapsulating material for display according to any one of [13] to [13].
본 발명의 디스플레이용 봉지제는, 유연성과 저투습성을 양립할 수 있는 것이기 때문에, 디스플레이용 봉지제로서 유용하다.INDUSTRIAL APPLICABILITY The encapsulant for display of the present invention is useful as an encapsulant for displays because it can be compatible with flexibility and low moisture permeability.
[(A) 분자 내에 3 이상의 비스페놀 골격 및, 3 이상의 반응성 관능기를 갖는 경화성 화합물][(A) a curable compound having three or more bisphenol skeletons and three or more reactive functional groups in the molecule]
본 발명의 디스플레이용 봉지제는, (A): 분자 내에 3 이상의 비스페놀 골격 및, 3 이상의 반응성 관능기를 갖는 경화성 화합물(이하, 간단히 「성분 (A)」라고도 함)을 함유한다. 이 화합물은, 그 자체 일정한 유연성을 갖고, 또한 경화 반응 후에도 관능기의 많음을 이용한 고가교 밀도를 실현하기 때문에, 본 발명의 효과를 얻기 위해 필요하다. 나아가서는, 이 특성을 갖는 화합물은, 소량의 첨가로도 충분한 효과를 얻을 수 있는 것에 특징이 있다.The encapsulating material for display of the present invention comprises (A): a curing compound having three or more bisphenol skeletons and three or more reactive functional groups in the molecule (hereinafter, simply referred to as "component (A)"). This compound is required to obtain the effect of the present invention because it has a certain degree of flexibility and realizes high-density crosslinking using a large number of functional groups even after the curing reaction. Further, the compound having these properties is characterized in that a sufficient effect can be obtained even by adding a small amount.
성분 (A)는, 3 이상의 비스페놀 골격을 갖는다. 비스페놀 골격이란 하기식 (1)로 나타나는 골격을 의미하고, 바람직하게는 비스페놀 A골격이다. 따라서, 성분 (A)로서도, 3 이상의 비스페놀 골격 중, 2 이상이 비스페놀 A 골격인 경우가 바람직하다.Component (A) has three or more bisphenol skeletons. The bisphenol skeleton means a skeleton represented by the following formula (1), preferably a bisphenol A skeleton. Therefore, also as the component (A), it is preferable that at least two of the three or more bisphenol skeletons are bisphenol A skeletons.
(식 (1) 중 R은 CH2, CH(CH3), C(CH3)2, S, O, SO2를 나타냄)(In the formula (1), R represents CH 2 , CH (CH 3 ), C (CH 3 ) 2 , S, O, SO 2 )
성분 (A)는 3 이상의 반응성 관능기를 갖는다. 반응성 관능기란, 반응성 이중 결합(비닐기, 알릴기, (메타)아크릴로일기 등), 환상 에테르기(에폭시기, 글리시딜기, 옥세타닐기 등), 카복실기, 하이드록시기, 아미노기, 하이드라지드기, 티올기 등을 의미한다. 이 중, 반응성 이중 결합인 경우가 바람직하고, 3 이상의 반응성 관능기 중 2 이상이 반응성 이중 결합인 경우가 더욱 바람직하다. 또한, 2 이상이 (메타)아크릴로일기인 경우가 특히 바람직하고, 3 이상이 (메타)아크릴로일기인 경우가 가장 바람직하다. 반응성 관능기의 수로서는, 3 이상이라면 특별히 한정되지 않지만, 3∼6인 경우가 바람직하고, 3 또는 4인 경우가 특히 바람직하다.Component (A) has three or more reactive functional groups. Examples of the reactive functional group include reactive double bonds (vinyl group, allyl group, (meth) acryloyl group and the like), cyclic ether group (epoxy group, glycidyl group, oxetanyl group and the like), carboxyl group, hydroxyl group, Zwitterionic group, thiol group, and the like. Among them, a reactive double bond is preferable, and it is more preferable that at least two of the three or more reactive functional groups are reactive double bonds. The case where two or more is a (meth) acryloyl group is particularly preferable, and a case where three or more is a (meth) acryloyl group is most preferable. The number of reactive functional groups is not particularly limited as long as it is 3 or more, but is preferably 3 to 6, and particularly preferably 3 or 4.
성분 (A)는 유연성, 접착성의 관점에서, 분자 내에 에스테르기나 수산기를 갖는 것이 바람직하다. 에스테르기를 갖는 경우, 에스테르기는 3개 이상 갖는 것이 바람직하고, 6개 이상 갖는 것이 더욱 바람직하다. 수산기를 갖는 경우, 수산기는 3개 이상 갖는 것이 바람직하다.From the viewpoints of flexibility and adhesiveness, the component (A) preferably has an ester group or a hydroxyl group in the molecule. In the case of having an ester group, the number of ester groups is preferably 3 or more, more preferably 6 or more. When having a hydroxyl group, it is preferable to have three or more hydroxyl groups.
성분 (A)는, 중량 평균 분자량이 1000 이상인 경우가 바람직하고, 더욱 바람직하게는 1200 이상이다. 바람직한 상한값은 5000 이하이고, 더욱 바람직하게는 3000 이하이다. 중량 평균 분자량이 상기 범위에 있음으로써, 경화물의 유연성, 구체적으로는 저탄성률, 고파단점 신도에 기여한다. 또한, 디스플레이용 봉지제가 적절한 점도 범위가 된다.The component (A) preferably has a weight average molecular weight of 1000 or more, more preferably 1,200 or more. The upper limit value is preferably 5000 or less, and more preferably 3000 or less. The weight average molecular weight in the above range contributes to the flexibility of the cured product, specifically, the low modulus of elasticity and the extinction ratio of the cords. In addition, the encapsulant for the display has an appropriate viscosity range.
또한, 반응성기 당량으로서는, 300∼700이 바람직하고, 더욱 바람직하게는 400∼600이다.The reactive group equivalent is preferably 300 to 700, more preferably 400 to 600.
또한, 성분 (A)의 바람직한 함유량은, 디스플레이용 봉지제 총량 중, 통상 5∼50질량%, 바람직하게는 5∼30질량%, 더욱 바람직하게는 10∼20질량%이다.The content of the component (A) is preferably 5 to 50% by mass, preferably 5 to 30% by mass, and more preferably 10 to 20% by mass, based on the total amount of the encapsulating agent for displays.
[(B) 경화성 화합물][(B) Curable compound]
본 발명의 디스플레이용 봉지제는, 성분 (B)로서, 경화성 화합물(이하, 간단히 「성분 (B)」라고도 함)을 함유한다.The encapsulant for display of the present invention contains a curable compound (hereinafter also simply referred to as " component (B) ") as the component (B).
성분 (B)로서는, 빛이나 열 등에 의해 경화하는 화합물이라면 특별히 한정되지 않지만, (B-1) (메타)아크릴 화합물(이하, 간단히 「성분 (B-1)」이라고도 함)인 경우가 바람직하다.The component (B) is not particularly limited as long as it is a compound cured by light or heat, but it is preferably a (B-1) (meth) acrylic compound (hereinafter simply referred to as "component (B-1) .
여기에서 「(메타)아크릴」이란 「아크릴」및/또는 「메타크릴」을 의미한다(이하 동일). 성분 (B-1)로서는, 예를 들면, (메타)아크릴에스테르 화합물, 에폭시(메타)아크릴레이트 화합물 등을 들 수 있다.Here, "(meth) acrylic" means "acryl" and / or "methacryl" (the same applies hereinafter). Examples of the component (B-1) include a (meth) acrylic ester compound and an epoxy (meth) acrylate compound.
[(B-1) (메타)아크릴 화합물][(B-1) (meth) acrylic compound]
(메타)아크릴에스테르 화합물의 구체예로서는, N-아크릴로일옥시에틸헥사하이드로프탈이미드, 아크릴로일모르폴린, 2-하이드록시프로필(메타)아크릴레이트, 4-하이드록시부틸(메타)아크릴레이트, 사이클로헥산-1,4-디메탄올모노(메타)아크릴레이트, 테트라하이드로푸르푸릴(메타)아크릴레이트, 페녹시에틸(메타)아크릴레이트, 페닐폴리에톡시(메타)아크릴레이트, 2-하이드록시-3-페닐옥시프로필(메타)아크릴레이트, o-페닐페놀모노에톡시(메타)아크릴레이트, o-페닐페놀폴리에톡시(메타)아크릴레이트, p-쿠밀페녹시에틸(메타)아크릴레이트, 이소보닐(메타)아크릴레이트, 트리브로모페닐옥시에틸(메타)아크릴레이트, 디사이클로펜타닐(메타)아크릴레이트, 디사이클로펜테닐(메타)아크릴레이트, 디사이클로펜테닐옥시에틸(메타)아크릴레이트, 1,4-부탄디올디(메타)아크릴레이트, 1,6-헥산디올디(메타)아크릴레이트, 1,9-노난디올디(메타)아크릴레이트, 트리사이클로데칸디메탄올(메타)아크릴레이트, 비스페놀 A 폴리에톡시디(메타)아크릴레이트, 비스페놀 A 폴리프로폭시디(메타)아크릴레이트, 비스페놀 F 폴리에톡시디(메타)아크릴레이트, 에틸렌글리콜디(메타)아크릴레이트, 폴리에틸렌글리콜디(메타)아크릴레이트, 트리스(아크릴옥시에틸)이소시아누레이트, 펜타에리트리톨테트라(메타)아크릴레이트, 디펜타에리트리톨헥사(메타)아크릴레이트, 디펜타에리트리톨펜타(메타)아크릴레이트, 트리펜타에리트리톨헥사(메타)아크릴레이트, 트리펜타에리트리톨펜타(메타)아크릴레이트, 트리메틸올프로판트리(메타)아크릴레이트, 트리메틸올프로판폴리에톡시트리(메타)아크릴레이트, 디트리메틸올프로판테트라(메타)아크릴레이트, 네오펜틸글리콜과 하이드록시피발린산의 에스테르디아크릴레이트나 네오펜틸글리콜과 하이드록시피발린산의 에스테르의 ε-카프로락톤 부가물의 디아크릴레이트 등의 모노머류를 들 수 있다. 바람직하게는, N-아크릴로일옥시에틸헥사하이드로프탈이미드, 페녹시에틸(메타)아크릴레이트, 디사이클로펜테닐옥시에틸(메타)아크릴레이트를 들 수 있다.Specific examples of the (meth) acrylic ester compound include N-acryloyloxyethylhexahydrophthalimide, acryloylmorpholine, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) (Meth) acrylate, phenoxyethyl (meth) acrylate, phenylpolyethoxy (meth) acrylate, 2-hydroxydiphenylethoxy (meth) acrylate, cyclohexane-1,4-dimethanol mono (meth) acrylate, tetrahydrofurfuryl (Meth) acrylate, o-phenylphenol monoethoxy (meth) acrylate, o-phenylphenol polyethoxy (meth) acrylate, p-cumylphenoxyethyl (Meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, dicyclopentanyl , 1,4-butane di (Meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, tricyclodecanedimethanol (meth) acrylate, bisphenol A polyethoxydi (Meth) acrylate, bisphenol A polypropoxydi (meth) acrylate, bisphenol F polyethoxydi (meth) acrylate, ethylene glycol di (meth) acrylate, polyethylene glycol di (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tripentaerythritol hexa (meth) acrylate, (Meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane polyethoxy tri (meth) acrylate, ditrimethylolpropane tri (Meth) acrylate, ester diacrylate of neopentyl glycol and hydroxypivalic acid, diacrylate of neopentyl glycol and? -Caprolactone adduct of ester of hydroxypivalic acid, and the like . Preferred are N-acryloyloxyethylhexahydrophthalimide, phenoxyethyl (meth) acrylate and dicyclopentenyloxyethyl (meth) acrylate.
에폭시(메타)아크릴레이트 화합물은, 에폭시 화합물과 (메타)아크릴산의 반응에 의해 공지의 방법으로 얻어진다. 원료가 되는 에폭시 화합물로서는, 특별히 한정되는 것은 아니지만, 2관능 이상의 에폭시 화합물이 바람직하고, 예를 들면, 레조르신디글리시딜에테르, 비스페놀 A형 에폭시 화합물, 비스페놀 F형 에폭시 화합물, 비스페놀 S형 에폭시 화합물, 페놀노볼락형 에폭시 화합물, 크레졸노볼락형 에폭시 화합물, 비스페놀 A 노볼락형 에폭시 화합물, 비스페놀 F 노볼락형 에폭시 화합물, 지환식 에폭시 화합물, 지방족 쇄상 에폭시 화합물, 글리시딜에스테르형 에폭시 화합물, 글리시딜아민형 에폭시 화합물, 히단토인형 에폭시 화합물, 이소시아누레이트형 에폭시 화합물, 트리페놀메탄 골격을 갖는 페놀노볼락형 에폭시 화합물, 그 외, 카테콜, 레조르시놀 등의 2관능 페놀류의 디글리시딜에테르화물, 2관능 알코올류의 디글리시딜에테르화물 및, 그들의 할로겐화물, 수소 첨가물 등을 들 수 있다. 이들 중 액정 오염성의 관점에서, 비스페놀 A형 에폭시 화합물이나 레조르신디글리시딜에테르가 바람직하다. 또한, 에폭시기와 (메타)아크릴로일기의 비율은 한정되는 것은 아니고, 공정 적합성의 관점에서 적절히 선택된다. 또한 에폭시기의 일부를 아크릴에스테르화하는 부분 에폭시(메타)아크릴레이트가 적합하게 사용된다. 이 경우의 아크릴화의 비율은, 30∼70% 정도가 바람직하다.The epoxy (meth) acrylate compound is obtained by a known method by the reaction of an epoxy compound with (meth) acrylic acid. The epoxy compound to be used as the raw material is not particularly limited, but is preferably an epoxy compound having two or more functionalities, and examples thereof include resorcinol diglycidyl ether, bisphenol A type epoxy compound, bisphenol F type epoxy compound, bisphenol S type epoxy A cresol novolak type epoxy compound, a bisphenol A novolak type epoxy compound, a bisphenol F novolak type epoxy compound, an alicyclic epoxy compound, an aliphatic chain epoxy compound, a glycidyl ester type epoxy compound, A bifunctional phenol compound such as a glycidylamine type epoxy compound, a hydantoin type epoxy compound, an isocyanurate type epoxy compound, a phenol novolak type epoxy compound having a triphenol methane skeleton, and other catechol and resorcinol Diglycidyl etherified diglycidyl ether compounds, diglycidyl ether compounds of bifunctional alcohols, and halogen Water, may be mentioned a hydrogenated product or the like. Among them, bisphenol A type epoxy compounds and resorcin diglycidyl ether are preferable from the viewpoint of liquid crystal staining property. In addition, the ratio of the epoxy group and the (meth) acryloyl group is not limited, and is appropriately selected from the viewpoint of process suitability. Further, a partial epoxy (meth) acrylate for acrylic esterifying a part of the epoxy group is suitably used. In this case, the ratio of acrylation is preferably about 30 to 70%.
성분 (B-1)은 단독으로 이용해도 좋고, 2종류 이상을 혼합해도 좋다. 본 발명의 디스플레이용 봉지제에 있어서, 성분 (B-1)을 사용하는 경우에는, 디스플레이용 봉지제 총량 중, 통상 5∼50질량%, 바람직하게는 5∼30질량%이다.Component (B-1) may be used alone or in combination of two or more kinds. When the component (B-1) is used in the sealing agent for a display of the present invention, it is usually 5 to 50 mass%, preferably 5 to 30 mass%, of the total amount of the encapsulating agent for display.
[(B-2) 에폭시 화합물][(B-2) epoxy compound]
본 발명의 실시 형태로서, 상기 성분 (B) 중에, 추가로 성분 (B-2) 에폭시 화합물(이하, 간단히 「성분 (B-2)」라고도 함)이 함유되는 경우가 더욱 바람직하다.As an embodiment of the present invention, it is more preferable that the component (B) further contains an epoxy compound (hereinafter also simply referred to as "component (B-2)") as the component (B-2).
에폭시 화합물로서는 특별히 한정되는 것은 아니지만, 2관능 이상의 에폭시 화합물이 바람직하고, 예를 들면, 레조르신디글리시딜에테르, 비스페놀 A형 에폭시 수지, 비스페놀 F형 에폭시 수지, 비스페놀 S형 에폭시 수지, 페놀노볼락형 에폭시 수지, 크레졸노볼락형 에폭시 수지, 비스페놀 A 노볼락형 에폭시 수지, 비스페놀 F 노볼락형 에폭시 수지, 지환식 에폭시 수지, 지방족 쇄상 에폭시 수지, 글리시딜에스테르형 에폭시 수지, 글리시딜아민형 에폭시 수지, 히단토인형 에폭시 수지, 이소시아누레이트형 에폭시 수지, 트리페놀메탄 골격을 갖는 페놀노볼락형 에폭시 수지, 그 외, 카테콜, 레조르시놀 등의 2관능 페놀류의 디글리시딜에테르화물, 2관능 알코올류의 디글리시딜에테르화물 및, 그들의 할로겐화물, 수소 첨가물 등을 들 수 있다. 이들 중 액정 오염성의 관점에서, 비스페놀 A형 에폭시 수지나 레조르신디글리시딜에테르가 바람직하다.The epoxy compound is not particularly limited, but is preferably an epoxy compound having two or more functional groups. Examples thereof include resorcin sodium glycidyl ether, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, Cresol novolak type epoxy resin, bisphenol A novolak type epoxy resin, bisphenol F novolak type epoxy resin, alicyclic epoxy resin, glycidyl ester type epoxy resin, glycidyl amine Type epoxy resins, epoxy resins such as epoxy resin, epoxy resin, epoxy resin, isocyanurate epoxy resin, phenol novolac epoxy resin having triphenol methane skeleton, diglycidyls of bifunctional phenols such as catechol and resorcinol Etherified products, diglycidyl etherified products of bifunctional alcohols, and their halides, hydrogenated products and the like. Among them, bisphenol A type epoxy resin and resorcin sodium glycidyl ether are preferable from the viewpoint of liquid crystal staining property.
성분 (B-2)는 단독으로 이용해도 좋고, 2종류 이상을 혼합해도 좋다. 본 발명의 디스플레이용 봉지제에 있어서, 성분 (B-2)를 사용하는 경우에는, 디스플레이용 봉지제 총량 중, 통상 5∼50질량%, 바람직하게는 5∼30질량%이다.Component (B-2) may be used alone or in combination of two or more kinds. When the component (B-2) is used in the sealing agent for a display of the present invention, it is usually 5 to 50 mass%, preferably 5 to 30 mass%, of the total amount of the encapsulating agent for display.
또한, 본 발명의 디스플레이용 봉지제에 있어서, 성분 (B)의 배합량은, 디스플레이용 봉지제의 총량 중, 통상 10∼80질량%, 바람직하게는 20∼70질량%이다. 성분 (B-1)과 성분 (B-2)를 혼합하여 사용하는 경우의 배합량도 동일하게 한다.In the sealing agent for a display of the present invention, the amount of the component (B) to be blended is usually 10 to 80% by mass, preferably 20 to 70% by mass, based on the total amount of the encapsulating agent for displays. When the component (B-1) and the component (B-2) are mixed and used, the blending amount is also the same.
[(C) 유기 필러][(C) organic filler]
본 발명의 디스플레이용 봉지제는, 성분 (C)로서 유기 필러(이하, 간단히 「성분 (C)」라고도 함)를 함유해도 좋다. 상기 유기 필러로서는, 예를 들면 우레탄 미립자, 아크릴 미립자, 스티렌 미립자, 스티렌올레핀 미립자 및 실리콘 미립자를 들 수 있다. 또한 실리콘 미립자로서는 KMP-594, KMP-597, KMP-598(신에츠 카가쿠 고교 제조), 토레필RTM E-5500, 9701, EP-2001(토레 다우코닝사 제조)이 바람직하고, 우레탄 미립자로서는 JB-800T, HB-800BK(네가미 고교 가부시키가이샤), 스티렌 미립자로서는 라발론RTM T320C, T331C, SJ4400, SJ5400, SJ6400, SJ4300C, SJ5300C, SJ6300C(미츠비시 카가쿠 제조)가 바람직하고, 스티렌올레핀 미립자로서는 셉톤RTM SEPS2004, SEPS2063이 바람직하다.The sealing agent for a display of the present invention may contain an organic filler (hereinafter, simply referred to as "component (C)") as the component (C). Examples of the organic filler include urethane fine particles, acrylic fine particles, styrene fine particles, styrene olefin fine particles and silicon fine particles. As the silicon fine particles, KMP-594, KMP-597, KMP-598 (Shinetsu Kagaku Kogyo), Torayfil RTM E-5500, 9701 and EP-2001 800T, HB-800BK (you US Kogyo Co., Ltd.), styrene fine particles as referred Balon RTM T320C, T331C, SJ4400, SJ5400, SJ6400, SJ4300C, SJ5300C, SJ6300C (manufactured by Mitsubishi Kagaku, Ltd.) are preferable, and septon as styrene-olefin particles RTM SEPS2004 and SEPS2063 are preferred.
이들 유기 필러는 단독으로 이용해도 좋고, 2종 이상을 병용해도 좋다. 또한 2종 이상을 이용하여 코어쉘 구조로 해도 좋다. 이들 중, 바람직하게는, 아크릴 미립자, 실리콘 미립자이다.These organic fillers may be used alone or in combination of two or more kinds. The core shell structure may be formed by using two or more kinds. Of these, preferred are acrylic fine particles and silicon fine particles.
상기 아크릴 미립자를 사용하는 경우, 2종류의 아크릴 고무로 이루어지는 코어쉘 구조의 아크릴고무인 경우가 바람직하고, 특히 바람직하게는 코어층이 n-부틸아크릴레이트이고, 쉘층이 메틸메타크릴레이트인 것이 바람직하다. 이는 제피악RTM F-351로서 아이카 고교 가부시키가이샤로부터 판매되고 있다.In the case of using the acrylic fine particles, acrylic rubber having a core shell structure composed of two types of acrylic rubber is preferable, and it is particularly preferable that the core layer is n-butyl acrylate and the shell layer is methyl methacrylate . It is sold by Aika Kogyo Co., Ltd. as Zephyr RTM F-351.
또한, 상기 실리콘 미립자로서는, 오르가노폴리실록산 가교물 분체, 직쇄의 디메틸폴리실록산 가교물 분체 등을 들 수 있다. 또한, 복합 실리콘 고무로서는, 상기 실리콘 고무의 표면에 실리콘 수지(예를 들면, 폴리오르가노실세스퀴옥산 수지)를 피복한 것을 들 수 있다. 이들 미립자 중, 특히 바람직한 것은, 직쇄의 디메틸폴리실록산 가교 분말의 실리콘 고무 또는 실리콘 수지 피복 직쇄 디메틸폴리실록산 가교 분말의 복합 실리콘 고무 미립자이다. 이들은, 단독으로 이용해도 좋고, 2종 이상을 병용해도 좋다. 또한, 바람직하게는, 고무 분말의 형상은, 첨가 후의 점도의 증점이 적은 구 형상이 좋다. 본 발명의 디스플레이용 봉지제에 있어서, 성분 (C)를 사용하는 경우에는, 디스플레이용 봉지제의 총량 중, 통상 5∼50질량%, 바람직하게는 5∼40질량%이다.Examples of the silicon fine particles include crosslinked organopolysiloxane powders and straight-chain dimethylpolysiloxane crosslinked powders. As the composite silicone rubber, a silicone rubber (for example, a polyorganosilsesquioxane resin) is coated on the surface of the silicone rubber. Particularly preferred among these fine particles are composite silicone rubber microparticles of silicone rubber or silicone resin-coated straight-chain dimethylpolysiloxane crosslinked powder of a straight-chain dimethylpolysiloxane crosslinked powder. These may be used alone, or two or more of them may be used in combination. Preferably, the shape of the rubber powder is a sphere having a small viscosity increase after the addition. When the component (C) is used in the sealing agent for a display of the present invention, it is usually 5 to 50 mass%, preferably 5 to 40 mass%, of the total amount of the encapsulating agent for display.
[(D) 무기 필러][(D) Inorganic filler]
본 발명의 디스플레이용 봉지제는, 성분 (D)로서, 무기 필러(이하, 간단히 성분 (D)라고도 함)를 함유해도 좋다. 본 발명에서 함유하는 무기 필러로서는, 실리카, 실리콘 카바이드, 질화 규소, 질화 붕소, 탄산 칼슘, 탄산 마그네슘, 황산 바륨, 황산 칼슘, 마이카, 탤크, 클레이, 알루미나, 산화 마그네슘, 산화 지르코늄, 수산화 알루미늄, 수산화 마그네슘, 규산 칼슘, 규산 알루미늄, 규산 리튬알루미늄, 규산 지르코늄, 티탄산 바륨, 유리 섬유, 탄소 섬유, 2황화 몰리브덴, 아스베스토 등을 들 수 있고, 바람직하게는 용융 실리카, 결정 실리카, 질화 규소, 질화 붕소, 탄산 칼슘, 황산 바륨, 황산 칼슘, 마이카, 탤크, 클레이, 알루미나, 수산화 알루미늄, 규산 칼슘, 규산 알루미늄을 들 수 있지만, 바람직하게는 실리카, 알루미나, 탤크이다. 이들 무기 필러는 2종 이상을 혼합하여 이용해도 좋다.The sealing agent for a display of the present invention may contain an inorganic filler (hereinafter, simply referred to as component (D)) as the component (D). Examples of the inorganic filler contained in the present invention include silica, silicon carbide, silicon nitride, boron nitride, calcium carbonate, magnesium carbonate, barium sulfate, calcium sulfate, mica, talc, clay, alumina, magnesium oxide, zirconium oxide, Examples of the inorganic filler include magnesium, calcium silicate, aluminum silicate, lithium aluminum silicate, zirconium silicate, barium titanate, glass fiber, carbon fiber, molybdenum disulfide and asbestos, and preferably fused silica, crystalline silica, , Calcium carbonate, barium sulfate, calcium sulfate, mica, talc, clay, alumina, aluminum hydroxide, calcium silicate and aluminum silicate, preferably silica, alumina and talc. These inorganic fillers may be used by mixing two or more kinds.
무기 필러의 평균 입자경은, 지나치게 크면 협갭의 액정 표시 셀 제조시에 상하 유리 기판의 접합 시의 갭 형성이 잘 되지 않는 등의 불량 요인이 되기 때문에, 2000㎚ 이하가 적당하고, 바람직하게는 1000㎚ 이하, 더욱 바람직하게는 300㎚ 이하이다. 또한 바람직한 하한은 10㎚ 정도이고, 더욱 바람직하게는 100㎚ 정도이다. 입자경은 레이저 회절·산란식 입도 분포 측정기(건식)(가부시키가이샤 세이신 기교 제조; LMS-30)에 의해 측정할 수 있다.If the average particle diameter of the inorganic filler is too large, it becomes a factor of failure such that the gap formation at the time of joining of the upper and lower glass substrates at the time of manufacturing the narrow gap liquid crystal cell is not made well. Therefore, the average particle diameter is preferably 2000 nm or less, Or less, more preferably 300 nm or less. A preferable lower limit is about 10 nm, and more preferably about 100 nm. The particle size can be measured by a laser diffraction / scattering type particle size distribution analyzer (dry type) (LMS-30, manufactured by Seishin Kogyo Co., Ltd.).
본 발명의 디스플레이용 봉지제에 있어서, 무기 필러를 사용하는 경우에는, 디스플레이용 봉지제의 총량 중, 통상 5∼50질량%, 바람직하게는 5∼40질량%이다. 무기 필러의 함유량이 5질량%보다 낮은 경우, 유리 기판에 대한 접착 강도가 저하하고, 또한 내습 신뢰성도 떨어지기 때문에, 흡습 후의 접착 강도의 저하도 커지는 경우가 있다. 또한, 무기 필러의 함유량이 50질량%보다 많은 경우, 필러 함유량이 지나치게 많기 때문에, 찌부러지기 어려워 액정 셀의 갭 형성을 할 수 없게 되어 버리는 경우가 있다.When an inorganic filler is used in the sealing agent for a display of the present invention, it is usually 5 to 50 mass%, preferably 5 to 40 mass%, of the total amount of the sealing agent for display. When the content of the inorganic filler is lower than 5% by mass, the bonding strength to the glass substrate decreases and the moisture resistance reliability deteriorates, so that the lowering of the bonding strength after moisture absorption is also increased. When the content of the inorganic filler is more than 50% by mass, the content of the filler is excessively large, so that it is hard to crumble and the gap of the liquid crystal cell can not be formed in some cases.
[(E) 실란 커플링제][(E) Silane coupling agent]
본 발명의 디스플레이용 봉지제는, 성분 (E)로서 실란 커플링제(이하, 간단히 「성분 (E)」라고도 함)를 첨가하여, 접착 강도나 내습성의 향상을 도모할 수 있다.The sealant for display of the present invention can be improved in adhesion strength and moisture resistance by adding a silane coupling agent (hereinafter, simply referred to as " component (E) ") as component (E).
성분 (E)로서는, 3-글리시독시프로필트리메톡시실란, 3-글리시독시프로필메틸디메톡시실란, 3-글리시독시프로필메틸디에톡시실란, 2-(3,4-에폭시사이클로헥실)에틸트리메톡시실란, N-페닐-γ-아미노프로필트리메톡시실란, N-(2-아미노에틸)3-아미노프로필메틸디메톡시실란, N-(2-아미노에틸)3-아미노프로필메틸트리메톡시실란, 3-아미노프로필트리에톡시실란, 3-메르캅토프로필트리메톡시실란, 비닐트리메톡시실란, N-(2-(비닐벤질아미노)에틸)3-아미노프로필트리메톡시실란 염산염, 3-메타크릴옥시프로필트리메톡시실란, 3-클로로프로필메틸디메톡시실란, 3-클로로프로필트리메톡시실란 등을 들 수 있다. 이들 실란 커플링제는 KBM 시리즈, KBE 시리즈 등으로서 신에츠 카가쿠 고교 가부시키가이샤 등에 의해 판매되고 있기 때문에, 시장으로부터 용이하게 입수 가능하다. 본 발명의 디스플레이용 봉지제에 있어서, 성분 (E)를 사용하는 경우에는, 디스플레이용 봉지제 총량 중, 0.05∼3질량%가 적합하다.Examples of the component (E) include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) Aminopropyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) 3-aminopropyltrimethoxysilane, vinyltrimethoxysilane, N- (2- (vinylbenzylamino) ethyl) 3-aminopropyltrimethoxysilane hydrochloride , 3-methacryloxypropyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, and the like. These silane coupling agents are commercially available from the market because they are sold by Shin-Etsu Chemical Co., Ltd. as KBM series, KBE series, and the like. When the component (E) is used in the sealing agent for a display of the present invention, 0.05 to 3% by mass is suitable for the total amount of encapsulating agent for display.
[(F) 열 경화제][(F) Thermal curing agent]
본 발명의 디스플레이용 봉지제는, 성분 (F)로서 열 경화제(이하, 간단히 「성분 (F)」라고도 함)를 첨가하여, 반응성의 향상을 도모할 수 있다.The sealing agent for a display of the present invention can be improved in reactivity by adding a heat curing agent (hereinafter also simply referred to as " component (F) ") as the component (F).
성분 (F)로서는, 예를 들면, 분자 내에 방향환에 결합한 카복실기를 갖는 화합물, 다가 아민류, 다가 페놀류, 유기산 하이드라지드 화합물 등을 들 수 있다. 단, 이들에 한정되는 것은 아니다. 예를 들면, 방향족 하이드라지드인 테레프탈산 디하이드라지드, 이소프탈산 디하이드라지드, 2,6-나프토산 디하이드라지드, 2,6-피리딘디하이드라지드, 1,2,4-벤젠트리하이드라지드, 1,4,5,8-나프토산 테트라하이드라지드, 피로멜리트산 테트라하이드라지드 등을 들 수 있다. 또한, 지방족 하이드라지드 화합물이라면, 예를 들면, 포름하이드라지드, 아세토하이드라지드, 프로피온산 하이드라지드, 옥살산 디하이드라지드, 말론산 디하이드라지드, 숙신산 디하이드라지드, 글루타르산 디하이드라지드, 아디프산 디하이드라지드, 피멜산 디하이드라지드, 세바스산 디하이드라지드, 1,4-사이클로헥산디하이드라지드, 주석산 디하이드라지드, 말산 디하이드라지드, 이미노디아세트산 디하이드라지드, N,N'-헥사메틸렌비스세미카바자이드, 구연산 트리하이드라지드, 니트릴로아세트산 트리하이드라지드, 사이클로헥산트리카본산 트리하이드라지드, 1,3-비스(하이드라지노카보노에틸)-5-이소프로필히단토인 등의 히단토인 골격, 바람직하게는 발린히단토인 골격(히단토인환의 탄소 원자가 이소프로필기로 치환된 골격)을 갖는 디하이드라지드 화합물, 트리스(1-하이드라지노카보닐메틸)이소시아누레이트, 트리스(2-하이드라지노카보닐에틸)이소시아누레이트, 트리스(1-하이드라지노카보닐에틸)이소시아누레이트, 트리스(3-하이드라지노카보닐프로필)이소시아누레이트, 비스(2-하이드라지노카보닐에틸)이소시아누레이트 등을 들 수 있다. 경화 반응성과 잠재성의 균형에서 바람직하게는, 이소프탈산 디하이드라지드, 말론산 디하이드라지드, 아디프산 디하이드라지드, 트리스(1-하이드라지노카보닐메틸)이소시아누레이트, 트리스(1-하이드라지노카보닐에틸)이소시아누레이트, 트리스(2-하이드라지노카보닐에틸)이소시아누레이트, 트리스(3-하이드라지노카보닐프로필)이소시아누레이트이고, 특히 바람직하게는 트리스(2-하이드라지노카보닐에틸)이소시아누레이트이다.As the component (F), for example, a compound having a carboxyl group bonded to an aromatic ring in a molecule, a polyvalent amine, a polyhydric phenol, an organic acid hydrazide compound and the like can be given. However, the present invention is not limited thereto. For example, aromatic hydrazide such as terephthalic acid dihydrazide, isophthalic acid dihydrazide, 2,6-naphthoic acid dihydrazide, 2,6-pyridine dihydrazide, 1,2,4-benzene Trihydrazide, 1,4,5,8-naphthoic acid tetrahydrazide, pyromellitic acid tetrahydrazide, and the like. The aliphatic hydrazide compound may be, for example, form hydrazide, acetohydrazide, propionic acid hydrazide, oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid Dihydrazide, adipic acid dihydrazide, pimelan dihydrazide, sebacic acid dihydrazide, 1,4-cyclohexane dihydrazide, tartaric acid dihydrazide, malic acid dihydrazide, N, N'-hexamethylene bis-semicarbazide, citric acid trihydrazide, nitriloacetic acid trihydrazide, cyclohexanetricarboxylic acid trihydrazide, 1,3-bis ( Dihydrazinocarbonyl) -5-isopropylhydantoin, preferably a valine hydantoin skeleton (a skeleton in which the carbon atom of the hydantoin ring is substituted with an isopropyl group) (1-hydrazinocarbonylmethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, tris (1-hydrazinocarbonylethyl) iso (3-hydrazinocarbonylpropyl) isocyanurate, bis (2-hydrazinocarbonylethyl) isocyanurate, and the like. In view of the balance between the curing reactivity and the potential, it is preferable to use an isophthalic acid dihydrazide, malonic acid dihydrazide, adipic acid dihydrazide, tris (1-hydrazinocarbonylmethyl) isocyanurate, tris (3-hydrazinocarbonylethyl) isocyanurate, tris (2-hydrazinocarbonylethyl) isocyanurate, and tris (3-hydrazinocarbonylpropyl) Is tris (2-hydrazinocarbonylethyl) isocyanurate.
성분 (F)로서는 분자 내에 방향환에 결합한 카복실기를 갖는 화합물을 사용하는 것이 바람직하고, 예를 들면, 4-하이드록시벤조산, 티오살리틸산, 테레프탈산, 시트라진산, 4-아미노벤조산, 4-(아미노메틸)벤조산, 2-메르캅토니코틴산을 들 수 있다.As the component (F), it is preferable to use a compound having a carboxyl group bonded to an aromatic ring in the molecule. Examples thereof include 4-hydroxybenzoic acid, thiosalicylic acid, terephthalic acid, Aminomethyl) benzoic acid, and 2-mercaponicotinic acid.
성분 (F)는 단독으로 이용해도 좋고, 2종류 이상을 혼합해도 좋다. 본 발명의 디스플레이용 봉지제에 있어서, 성분 (F)는, 디스플레이용 봉지제 총량 중, 통상 0.1∼10질량%, 바람직하게는 0.1∼5질량%이다.Component (F) may be used alone or in combination of two or more kinds. In the sealing agent for a display of the present invention, the content of the component (F) is usually 0.1 to 10% by mass, preferably 0.1 to 5% by mass, based on the total amount of the encapsulating agent for displays.
본 발명의 디스플레이용 봉지제는, 경화 촉매를 첨가하여, 더욱 반응성의 향상을 도모할 수 있다. 경화 촉매로서는, 아민류나 이미다졸류를 들 수 있지만, 이미다졸류가 특히 적합하다. 이미다졸류로서는, 2-메틸이미다졸, 2-페닐이미다졸, 2-운데실이미다졸, 2-헵타데실이미다졸, 2-페닐-4-메틸이미다졸, 1-벤질-2-페닐이미다졸, 1-벤질-2-메틸이미다졸, 1-시아노에틸-2-메틸이미다졸, 1-시아노에틸-2-페닐이미다졸, 1-시아노에틸-2-운데실이미다졸, 2,4-디아미노-6(2'-메틸이미다졸(1'))에틸-s-트리아진, 2,4-디아미노-6(2'-운데실이미다졸(1'))에틸-s-트리아진, 2,4-디아미노-6(2'-에틸-4-메틸이미다졸(1'))에틸-s-트리아진, 2,4-디아미노-6(2'-메틸이미다졸(1'))에틸-s-트리아진·이소시아누르산 부가물, 2-메틸이미다졸이소시아누르산의 2:3 부가물, 2-페닐이미다졸이소시아누르산 부가물, 2-페닐-3,5-디하이드록시메틸이미다졸, 2-페닐-4-하이드록시메틸-5-메틸이미다졸, 1-시아노에틸-2-페닐-3,5-디시아노에톡시메틸이미다졸 등을 들 수 있다.The sealing agent for a display of the present invention can further improve the reactivity by adding a curing catalyst. Curing catalysts include amines and imidazoles, but imidazoles are particularly suitable. Examples of imidazoles include 2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenyl- Phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl- (2'-methylimidazole (1 ')) ethyl-s-triazine, 2,4-diamino-6 (2'-undecyl Imidazole (1 ')) ethyl-s-triazine, 2,4-diamino-6 (2'-ethyl-4-methylimidazole -Diamino-6 (2'-methylimidazole (1 ')) ethyl-s-triazine isocyanuric acid adduct, 2: 3 adduct of 2-methylimidazole isocyanuric acid, 2 Phenylimidazole isocyanuric acid adduct, 2-phenyl-3,5-dihydroxymethylimidazole, 2-phenyl-4-hydroxymethyl-5-methylimidazole, 1- Phenyl-3,5-dicyanoethoxymethylimidazole, and the like.
[(G) 광 라디칼 중합 개시제][(G) Photo radical polymerization initiator]
본 발명의 디스플레이용 봉지제는, 성분 (G)로서 광 라디칼 중합 개시제(이하, 간단히 「성분 (G)」라고도 함)를 함유해도 좋다. 광 라디칼 중합 개시제로서는, 자외선이나 가시광의 조사에 의해, 라디칼이나 산을 발생하고, 연쇄 중합 반응을 개시시키는 화합물이라면 특별히 한정되지 않지만, 예를 들면, 벤질디메틸케탈, 1-하이드록시사이클로헥실페닐케톤, 디에틸티옥산톤, 벤조페논, 2-에틸안트라퀴논, 2-하이드록시-2-메틸프로피오페논, 2-메틸-〔4-(메틸티오)페닐〕-2-모르폴리노-1-프로판, 2,4,6-트리메틸벤조일디페닐포스핀옥사이드, 캠퍼퀴논, 9-플루오레논, 디페닐디술피드 등을 들 수 있다. 구체적으로는, IRGACURERTM 651, 184, 2959, 127, 907, 369, 379 EG, 819, 784, 754, 500, OXE01, OXE02, OXE03, OXE04, DAROCURERTM 1173, LUCIRINRTM TPO(모두 BASF사 제조), 세이쿠올RTM Z, BZ, BEE, BIP, BBI(모두 세이코 카가쿠 가부시키가이샤 제조) 등을 들 수 있다. 이들 중에서, 바람직하게는, 옥심 에스테르계 개시제인 OXE01, OXE02, OXE03, OXE04이다.The encapsulant for display of the present invention may contain a photo radical polymerization initiator (hereinafter, simply referred to as " component (G) ") as the component (G). The photo radical polymerization initiator is not particularly limited as long as it is a compound which generates a radical or an acid upon irradiation with ultraviolet rays or visible light and initiates a chain polymerization reaction. Examples thereof include benzyl dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone Methylthiophenone, diethyl thioxanthone, benzophenone, 2-ethyl anthraquinone, 2-hydroxy-2-methylpropiophenone, 2- methyl- [4- (methylthio) Propane, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, camphorquinone, 9-fluorenone, and diphenyl disulfide. Specifically, the IRGACURE RTM 651, 184, 2959, 127, 907, 369, 379 EG, 819, 784, 754, 500, OXE01, OXE02, OXE03, OXE04, DAROCURE RTM 1173, LUCIRIN RTM TPO , SEQUOIL RTM Z, BZ, BEE, BIP, and BBI (all available from Seiko Chemical Industries, Ltd.). Of these, oxime ester-based initiators OXE01, OXE02, OXE03 and OXE04 are preferred.
또한, 액정 오염성의 관점에서, 분자 내에 (메타)아크릴기를 갖는 것을 사용하는 것이 바람직하고, 예를 들면 2-메타크릴로일옥시에틸이소시아네이트와 1-[4-(2-하이드록시에톡시)-페닐]-2-하이드록시-2메틸-1-프로판-1-온의 반응 생성물이 적합하게 이용된다. 이 화합물은 국제공개 제2006/027982호에 기재된 방법으로 제조하여 얻을 수 있다.From the viewpoint of liquid crystal staining property, it is preferable to use one having a (meth) acrylic group in the molecule, and examples thereof include 2- methacryloyloxyethyl isocyanate and 1- [4- (2-hydroxyethoxy) Phenyl] -2-hydroxy-2-methyl-1-propan-1-one are suitably used. This compound can be prepared by the method described in WO 2006/027982.
본 발명의 디스플레이용 봉지제에 있어서, 성분 (G)를 사용하는 경우에는, 디스플레이용 봉지제 총량 중, 통상 0.001∼3질량%, 바람직하게는 0.002∼2질량%이다.When the component (G) is used in the sealing agent for a display of the present invention, it is usually 0.001 to 3% by mass, preferably 0.002 to 2% by mass, based on the total amount of the encapsulating agent for displays.
[(H) 열 라디칼 중합 개시제][(H) thermal radical polymerization initiator]
본 발명의 디스플레이용 봉지제는, (H) 열 라디칼 중합 개시제(이하, 간단히 「성분 (H)」라고도 함)를 함유하여, 경화 속도, 경화성을 향상할 수 있다.The encapsulant for display of the present invention contains (H) a thermal radical polymerization initiator (hereinafter, simply referred to as " component (H) ") to improve the curing rate and curability.
열 라디칼 중합 개시제는, 가열에 의해 라디칼을 발생하여, 연쇄 중합 반응을 개시시키는 화합물이라면 특별히 한정되지 않지만, 유기 과산화물, 아조 화합물, 벤조인 화합물, 벤조인 에테르 화합물, 아세토페논 화합물, 벤조피나콜 등을 들 수 있고, 벤조피나콜이 적합하게 이용된다. 예를 들면, 유기 과산화물로서는, 카야멕RTM A, M, R, L, LH, SP-30C, 퍼카독스 CH-50L, BC-FF, 카독스 B-40ES, 퍼카독스 14, 트리고녹스RTM 22-70E, 23-C70, 121, 121-50E, 121-LS50E, 21-LS50E, 42, 42LS, 카야에스테르RTM P-70, TMPO-70, CND-C70, OO-50E, AN, 카야부틸RTM B, 퍼카독스 16, 카야카본RTM BIC-75, AIC-75(가야쿠아쿠조 가부시키가이샤 제조), 퍼멕RTM N, H, S, F, D, G, 퍼헥사RTM H, HC, TMH, C, V, 22, MC, 퍼큐어RTM AH, AL, HB, 퍼부틸RTM H, C, ND, L, 퍼큐밀RTM H, D, 퍼로일RTM IB, IPP, 퍼옥타RTM ND(니치유 가부시키가이샤 제조) 등이 시판품으로서 입수 가능하다.The thermal radical polymerization initiator is not particularly limited as long as it is a compound which generates radicals upon heating to initiate a chain polymerization reaction. Examples of the organic peroxide, azo compound, benzoin compound, benzoin ether compound, acetophenone compound, benzopinacol, etc. , And benzopinacol is suitably used. For example, as the organic peroxide, kaya MEC RTM A, M, R, L , LH, SP-30C, peoka DOX CH-50L, BC-FF, car DOX B-40ES, peoka DOX 14, teurigo Knox RTM 22- 70E, 23-C70, 121, 121-50E, 121-LS50E, 21-LS50E, 42, 42LS, Kaya ester RTM P-70, TMPO-70 , CND-C70, OO-50E, AN, kaya butyl RTM B, peoka DOX 16, kaya carbon RTM BIC-75, AIC-75 ( go exigua Kujo manufactured by whether or Ltd.), peomek RTM N, H, S, F, D, G, buffer hexahydro RTM H, HC, TMH, C, V , 22, MC, PERCURE RTM AH, AL, HB, PERBUTYL RTM H, C, ND, L, PERCYMIL RTM H, D, PEROYL RTM IB, IPP, PEROTA RTM ND (manufactured by Nichiyu K.K. ) Are commercially available.
또한, 아조 화합물로서는, VA-044, 086, V-070, VPE-0201, VSP-1001(와코준야쿠 고교 가부시키가이샤 제조) 등이 시판품으로서 입수 가능하다.As the azo compound, VA-044, 086, V-070, VPE-0201, VSP-1001 (manufactured by Wako Pure Chemical Industries, Ltd.) and the like are commercially available.
성분 (H)의 함유량으로서는, 본 발명의 디스플레이용 봉지제의 총량 중, 0.0001∼10질량%인 것이 바람직하고, 더욱 바람직하게는 0.0005∼5질량%이고, 0.001∼3질량%가 특히 바람직하다.The content of the component (H) is preferably from 0.0001 to 10 mass%, more preferably from 0.0005 to 5 mass%, and particularly preferably from 0.001 to 3 mass%, based on the total amount of the encapsulating material for display of the present invention.
본 발명의 디스플레이용 봉지제에는, 추가로 필요에 따라서, 라디칼 중합 방지제, 안료, 레벨링제, 소포제, 용제 등의 첨가제를 배합할 수 있다.If necessary, additives such as a radical polymerization inhibitor, a pigment, a leveling agent, a defoaming agent, and a solvent may be added to the encapsulating material for display of the present invention.
[라디칼 중합 방지제][Radical polymerization inhibitor]
상기 라디칼 중합 방지제로서는, 광 라디칼 중합 개시제나 열 라디칼 중합 개시제 등으로부터 발생하는 라디칼과 반응하여 중합을 방지하는 화합물이라면 특별히 한정되는 것은 아니고, 퀴논계, 피페리딘계, 힌더드페놀계, 니트로소계 등을 이용할 수 있다. 구체적으로는, 나프토퀴논, 2-하이드록시나프토퀴논, 2-메틸나프토퀴논, 2-메톡시나프토퀴논, 2,2,6,6-테트라메틸피페리딘-1-옥실, 2,2,6,6-테트라메틸-4-하이드록시피페리딘-1-옥실, 2,2,6,6-테트라메틸-4-메톡시피페리딘-1-옥실, 2,2,6,6-테트라메틸-4-페녹시피페리딘-1-옥실, 하이드로퀴논, 2-메틸하이드로퀴논, 2-메톡시하이드로퀴논, 파라벤조퀴논, 부틸화 하이드록시아니솔, 2,6-디-t-부틸-4-에틸페놀, 2,6-디-t-부틸크레졸, 스테아릴 β-(3,5-디-t-부틸-4-하이드록시페닐)프로피오네이트, 2,2'-메틸렌비스(4-에틸-6-t-부틸페놀), 4,4'-티오비스(3-메틸-6-t-부틸페놀), 4,4'-부틸리덴비스(3-메틸-6-t-부틸페놀), 3,9-비스[1,1-디메틸-2-[β-(3-t-부틸-4-하이드록시-5-메틸페닐)프로피오닐옥시]에틸], 2,4,8,10-테트라옥사스피로[5,5]운데칸, 테트라키스-[메틸렌-3-(3',5'-디-t-부틸-4'-하이드록시페닐프로피오네이트)메탄], 1,3,5-트리스(3',5'-디-t-부틸-4'-하이드록시벤질)-sec-트리아진-2,4,6-(1H, 3H, 5H)트리온, 파라메톡시페놀, 4-메톡시-1-나프톨, 티오디페닐아민, N-니트로소페닐하이드록시아민의 알루미늄염, 상품명 아데카스타브 LA-81, 상품명 아데카스타브 LA-82(가부시키가이샤 아데카 제조) 등을 들 수 있지만, 이들에 한정되는 것은 아니다. 이들 중 나프토퀴논계, 하이드로퀴논계, 니트로소계, 피페라진계의 라디칼 중합 방지제가 바람직하고, 나프토퀴논, 2-하이드록시나프토퀴논, 하이드로퀴논, 2,6-디-tert-부틸-P-크레졸, 폴리스톱 7300P(하쿠토 가부시키가이샤 제조)가 더욱 바람직하고, 폴리스톱 7300P(하쿠토 가부시키가이샤 제조)가 가장 바람직하다.The radical polymerization inhibitor is not particularly limited as long as it is a compound which reacts with a radical generated from a photo radical polymerization initiator or a thermal radical polymerization initiator to prevent polymerization, and examples thereof include quinone, piperidine, hindered phenol, Can be used. Specific examples include naphthoquinone, 2-hydroxynaphthoquinone, 2-methylnaphthoquinone, 2-methoxynaphthoquinone, 2,2,6,6-tetramethylpiperidine-1-oxyl, 2 , 2,6,6-tetramethyl-4-hydroxypiperidine-1-oxyl, 2,2,6,6-tetramethyl-4-methoxypiperidin- 2-methylhydroquinone, 2-methoxyhydroquinone, parabenzoquinone, butylated hydroxyanisole, 2,6-di-t-butoxycarbonylamino, Butyl-4-ethylphenol, 2,6-di-t-butylcresol, stearyl β- (3,5-di- (4-ethyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- (3-t-butyl-4-hydroxy-5-methylphenyl) propionyloxy] ethyl], 2,4,5- Tetraoxaspiro [5,5] undecane, tetrakis- [methylene-3- (3 ', 5'-di-t-butyl- (3 ', 5'-di-t-butyl-4'-hydroxybenzyl) -sec-triazine-2,4,6- , 3H, 5H) trione, paramethoxyphenol, 4-methoxy-1-naphthol, thiodiphenylamine, aluminum salt of N-nitrosophenylhydroxyamine, trade name Adecastab LA-81, And Tabla LA-82 (manufactured by Adeka Co., Ltd.), but the present invention is not limited thereto. Of these, radical polymerization inhibitors based on naphthoquinone, hydroquinone, nitroso and piperazine are preferable, and naphthoquinone, 2-hydroxynaphthoquinone, hydroquinone, 2,6-di-tert- -Cresol and polystop 7300P (manufactured by Hakuto K.K.) are more preferable, and polystop 7300P (manufactured by Hakuto K.K.) is most preferable.
라디칼 중합 방지제의 함유량으로서는 본 발명의 디스플레이용 봉지제의 총량 중, 0.0001∼1질량%가 바람직하고, 0.001∼0.5질량%가 더욱 바람직하고, 0.01∼0.2질량%가 특히 바람직하다.The content of the radical polymerization inhibitor is preferably from 0.0001 to 1% by mass, more preferably from 0.001 to 0.5% by mass, and particularly preferably from 0.01 to 0.2% by mass, based on the total amount of the encapsulating material for display of the present invention.
본 발명의 디스플레이용 봉지제를 얻는 방법의 일 예로서는, 다음에 나타내는 방법이 있다. 우선, 성분 (A), (B)에, 필요에 따라서 성분 (G)를 가열 용해한다. 이어서 실온까지 냉각 후, 필요에 따라서 성분 (C), (D), (E), (F), (H), 소포제 및, 레벨링제, 용제 등을 첨가하고, 공지의 혼합 장치, 예를 들면 3축롤, 샌드 밀, 볼 밀 등에 의해 균일하게 혼합하여, 금속 메시로 여과함으로써 본 발명의 디스플레이용 봉지제를 제조할 수 있다.As an example of a method for obtaining the encapsulant for display of the present invention, there is the following method. First, the component (G) is heated and dissolved in the components (A) and (B), if necessary. Subsequently, the mixture is cooled to room temperature and then added with components (C), (D), (E), (F), (H), antifoaming agents, leveling agents, solvents and the like, The mixture is homogeneously mixed with a three-roll mill, a sand mill, a ball mill or the like, and filtered through a metal mesh to produce the encapsulating material for display of the present invention.
또한, 본 발명의 디스플레이용 봉지제는, 액정 표시 셀용 접착제로서, 특히 액정 시일제로서 매우 유용하다. 본 발명의 디스플레이용 봉지제를 액정 시일제로서 이용한 경우의, 액정 표시 셀에 대해서, 이하에 예를 나타낸다.Further, the sealing agent for display of the present invention is very useful as an adhesive for a liquid crystal display cell, particularly as a liquid crystal sealing agent. An example of a liquid crystal display cell in the case of using the encapsulant for display of the present invention as a liquid crystal sealant is shown below.
본 발명의 액정 표시 셀용 접착제를 이용하여 제조되는 액정 표시 셀은, 기판에 소정의 전극을 형성한 한 쌍의 기판을 소정의 간격으로 대향 배치하고, 주위를 본 발명의 액정 시일제로 시일하고, 그 간극에 액정이 봉입된 것이다. 봉입되는 액정의 종류는 특별히 한정되지 않는다. 여기에서, 기판이란 유리, 석영, 플라스틱, 실리콘 등으로 이루어지는 적어도 한쪽에 광 투과성이 있는 조합의 기판으로 구성된다. 그 제법으로서는, 본 발명의 액정 시일제에, 유리 파이버 등의 스페이서(간극 제어재)를 첨가 후, 당해 한 쌍의 기판의 한쪽에 디스펜서, 또는 스크린 인쇄 장치 등을 이용하여 당해 액정 시일제를 도포한 후, 필요에 따라서, 80∼120℃에서 가경화를 행한다. 그 후, 당해 액정 시일제의 보(weir)의 내측에 액정을 적하하고, 진공 중에서 다른 한쪽의 유리 기판을 서로 겹쳐, 갭 만들기를 행한다. 갭 형성 후, 90∼130℃에서 30분∼2시간 경화함으로써 본 발명의 액정 표시 셀을 얻을 수 있다. 또한 광열 병용형으로서 사용하는 경우는, 자외선 조사기에 의해 액정 시일제부에 자외선을 조사시켜 광경화시킨다. 자외선 조사량은, 바람직하게는 500∼6000mJ/㎠, 보다 바람직하게는 1000∼4000mJ/㎠의 조사량이 바람직하다. 그 후 필요에 따라서, 90∼130℃에서 30분∼2시간 경화함으로써 본 발명의 액정 표시 셀을 얻을 수 있다. 이와 같이 하여 얻어진 본 발명의 액정 표시 셀은, 액정 오염에 의한 표시 불량이 없고, 접착성, 내습 신뢰성이 우수한 것이다. 스페이서로서는, 예를 들면 유리 파이버, 실리카 비즈, 폴리머 비즈 등을 들 수 있다. 그의 직경은, 목적에 따라 상이하지만, 통상 2∼8㎛, 바람직하게는 4∼7㎛이다. 그의 사용량은, 본 발명의 액정 시일제 100질량부에 대하여 통상 0.1∼4질량부, 바람직하게는 0.5∼2질량부, 더욱, 바람직하게는 0.9∼1.5질량부 정도이다.A liquid crystal display cell manufactured using an adhesive for a liquid crystal display cell of the present invention is a liquid crystal display cell in which a pair of substrates each having a predetermined electrode formed on a substrate are arranged opposite to each other at a predetermined interval and the periphery thereof is sealed with the liquid crystal sealant of the present invention, The gap is filled with liquid crystal. The type of the liquid crystal to be enclosed is not particularly limited. Here, the substrate is composed of a combination substrate made of glass, quartz, plastic, silicon or the like and having at least one light transmitting property. As a method for producing the liquid crystal sealing material, a spacer (gap control material) such as glass fiber is added to the liquid crystal sealing material of the present invention, and the liquid crystal sealing material is coated on one side of the pair of substrates using a dispenser or a screen printing apparatus After that, temporary curing is carried out at 80 to 120 캜, if necessary. Thereafter, liquid crystal is dropped inside the weir of the liquid crystal sealer, and the other glass substrate is superimposed on each other in vacuum to make a gap. After forming the gap, the liquid crystal display cell of the present invention can be obtained by curing at 90 to 130 캜 for 30 minutes to 2 hours. When it is used as a photothermal additive type, ultraviolet rays are irradiated to the liquid crystal seal part by an ultraviolet ray irradiator to cause photo curing. The ultraviolet irradiation dose is preferably an irradiation dose of 500 to 6000 mJ / cm 2, more preferably 1000 to 4000 mJ / cm 2. Thereafter, if necessary, the liquid crystal display cell of the present invention can be obtained by curing at 90 to 130 캜 for 30 minutes to 2 hours. The liquid crystal display cell of the present invention thus obtained is free from display defects due to liquid crystal contamination, and is excellent in adhesion and humidity resistance reliability. Examples of the spacer include glass fiber, silica beads, polymer beads, and the like. The diameter thereof varies depending on the purpose, but is usually 2 to 8 占 퐉, preferably 4 to 7 占 퐉. The amount thereof is usually from 0.1 to 4 parts by mass, preferably from 0.5 to 2 parts by mass, more preferably from 0.9 to 1.5 parts by mass, per 100 parts by mass of the liquid crystal sealing material of the present invention.
본 발명의 디스플레이용 봉지제는, 경화성, 상이한 피착체로의 접착성, 내습열 신뢰성이 요구되는 분야의 접착제 용도의 사용에 매우 적합한 것이다. 예를 들면 액정 시일제, 유기 EL용 봉지제, 터치 패널용 접착제이다.INDUSTRIAL APPLICABILITY The encapsulant for display of the present invention is very suitable for use in adhesive applications in areas where curability, adhesiveness to different adherends, and heat and moisture heat reliability are required. For example, a liquid crystal sealing agent, an encapsulating agent for organic EL, and an adhesive for a touch panel.
(실시예)(Example)
이하, 실시예에 의해 본 발명을 더욱 상세하게 설명하지만, 본 발명은 실시예에 한정되는 것은 아니다. 또한, 특별한 기재가 없는 한, 본문 중 「부」및 「%」라고 있는 것은 질량 기준이다.Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. In addition, unless otherwise specified, "parts" and "%" in the text are based on mass.
[합성예 1][Synthesis Example 1]
[피마자유 변성 에폭시 수지의 아크릴레이트화][Acrylation of castor oil-modified epoxy resin]
교반 장치, 환류관, 온도계를 부착한 플라스크 중에, 피마자유 변성 에폭시 수지 104g(제품명: EPOX-MKR151, 가부시키가이샤 프린텍 제조)을 톨루엔 120g에 용해하고, 이것에 중합 금지제로서 디부틸하이드록시톨루엔 0.4g을 더하여, 60℃까지 승온했다. 그 후, 에폭시기의 100%당량의 아크릴산 18.9g을 더하고 추가로 80℃까지 승온하고, 이에 반응 촉매인 트리메틸암모늄하이드록사이드 0.6g을 첨가하고, 98℃에서 약 40시간 교반하여, 반응액을 얻었다. 이 반응액을 물세정하여, 톨루엔을 증류 제거함으로써, 목적으로 하는 화합물 110g을 얻었다.104 g of castor-modified epoxy resin (product name: EPOX-MKR151, manufactured by Showa Denko K.K.) was dissolved in 120 g of toluene in a flask equipped with a stirrer, a reflux tube and a thermometer. To the flask was added dibutylhydroxytoluene And the temperature was raised to 60 占 폚. Thereafter, 18.9 g of 100% equivalent of acrylic acid as an epoxy group was added and the temperature was further raised to 80 캜. Then, 0.6 g of trimethylammonium hydroxide as a reaction catalyst was added and stirred at 98 캜 for about 40 hours to obtain a reaction solution . The reaction solution was water-washed, and toluene was distilled off to obtain 110 g of the target compound.
[실시예 1∼2, 비교예 1∼5][Examples 1 to 2 and Comparative Examples 1 to 5]
하기표 1에 나타내는 비율로 성분 (A), (B)를 혼합하고, 성분 (G)를 90℃에서 가열 용해시킨 후, 실온까지 냉각하여, 성분 (C), (D), (E), (F), (H), (O)를 첨가하고, 교반한 후, 3축 롤 밀로 분산시키고, 금속 메시(635 메시)로 여과하여, 디스플레이용 봉지제의 실시예 1, 2를 조제했다. 또한, 성분 (A)를 바꾸어, 성분 (O-3)∼(O-6)을 이용하여, 비교예 1∼5를 조제했다.(C), (D), (E), and (D) were mixed by mixing the components (A) and (B) in the proportions shown in Table 1 below, heating and dissolving the component (F), (H) and (O) were added and stirred. The mixture was dispersed with a three-axis roll mill and filtered with a metal mesh (635 mesh) to prepare Examples 1 and 2 of a sealing agent for displays. Comparative Examples 1 to 5 were prepared by using the components (O-3) to (O-6) in place of the component (A).
[평가][evaluation]
[접착 강도][Adhesive strength]
(초기 접착 강도 광 배향막)(Initial adhesion strength photo alignment layer)
유리 기판에 배향막액(닛산 카가쿠 고교 가부시키가이샤 제조: RN2880)을 스핀 코팅하고, 80℃ 핫 플레이트에서 3분 가소(假燒)를 행하여 230℃ 오븐에서 30분 소성했다. 또한, 이 배향막 부착 기판을 UV 조사기에 의해 500mJ/㎠(측정 파장: 254㎚)의 자외선을 조사시키고, 추가로 230℃ 오븐에서 30분 소성했다.An alignment film liquid (RN2880, manufactured by Nissan Kagaku Kogyo K.K.) was spin coated on the glass substrate, and the glass substrate was calcined in a hot plate at 80 캜 for 3 minutes and then baked in an oven at 230 캜 for 30 minutes. Further, the substrate with the alignment film was irradiated with ultraviolet light of 500 mJ / cm 2 (measurement wavelength: 254 nm) by a UV irradiator and further baked in an oven at 230 ° C for 30 minutes.
실시예 및 비교예에서 제조된 액정 시일제 100g에 스페이서로서 5㎛의 유리 파이버 1g을 첨가하여 혼합 교반을 행한다. 배향막을 도포한 유리 기판 상에, 이 액정 시일제를 1cm×1cm의 코너 부분을 재현하는 형(形)으로 도포하고, 대향의 배향막 도포 기판을 접합 UV 조사기에 의해 3000mJ/㎠의 자외선을 조사 후, 오븐에 투입하여 120℃ 1시간 열 경화시켰다. 그 배향막 도포 유리 기판의 떼어냄 접착 강도를 본드 테스터(세이신 쇼지 가부시키가이샤 제조: SS-30WD)로, 코너 부분을 누르는 형으로 측정했다. 강도를 표 1에 나타낸다.1 g of 5 m glass fiber as a spacer was added to 100 g of the liquid crystal sealant prepared in Examples and Comparative Examples, followed by mixing and stirring. This liquid crystal sealant was applied on a glass substrate coated with an alignment film in a shape reproducing a corner portion of 1 cm x 1 cm and irradiated with ultraviolet rays of 3000 mJ / cm < 2 > by a joining UV irradiator on the opposing alignment film- , And the mixture was placed in an oven and thermally cured at 120 ° C for 1 hour. The peel adhesion strength of the alignment film-coated glass substrate was measured with a bond tester (SS-30WD, manufactured by Seishin Shoji Co., Ltd.) by pressing the corner portion. Table 1 shows the strength.
(PCT 후 접착 강도 광 배향막)(Adhesion strength optical alignment film after PCT)
상기 배향막 도포 기판에 액정 시일제를 도포하고, 경화시킨 시험편을 PCT 시험(조건: 온도 121℃, 습도 100%, 기압 2atm, 시험 시간 12시간)에 걸쳐, 동일하게 접착 강도를 측정했다. 강도를 표 1에 나타낸다.A liquid crystal sealant was applied to the alignment film application substrate and the cured test piece was subjected to a PCT test (conditions: temperature: 121 캜, humidity: 100%, air pressure: 2 atm, test time: 12 hours) Table 1 shows the strength.
[유리 전이 온도 측정][Glass transition temperature measurement]
실시예, 비교예에서 제조된 액정 시일제를 폴리에틸렌테레프탈레이트(PET) 필름에 끼워 넣어 두께 100㎛의 박막으로 한 것을, UV 조사기에 의해 3000mJ/㎠의 자외선을 조사 후, 오븐에 투입하여 120℃ 1시간 열 경화시켰다. 경화 후 PET 필름을 벗겨 시일제 경화막을 얻은 후, 이것을 50㎜×5㎜의 직사각 형상으로 컷하여 샘플편으로 했다. 이 샘플편을 동적 점탄성 측정 장치(DMS-6100: 에스아이아이·나노테크놀로지사 제조)의 인장 모드에서 주파수 10Hz, 승온 온도 3℃/분의 조건으로 측정을 행하고, 손실 계수 Tanδ의 커브에 있어서 최댓값이 되는 온도를 유리 전이 온도로 하여 결과를 얻었다. 결과를 표 1에 나타낸다.The liquid crystal sealing agent prepared in Examples and Comparative Examples was sandwiched in a polyethylene terephthalate (PET) film to form a thin film having a thickness of 100 탆. The film was irradiated with ultraviolet rays of 3000 mJ / cm 2 by a UV irradiator, Lt; / RTI > for 1 hour. After the curing, the PET film was peeled off to obtain a seal cured film, which was then cut into a rectangular shape of 50 mm x 5 mm to obtain a sample piece. This sample piece was subjected to measurement under the conditions of a frequency of 10 Hz and a temperature rise temperature of 3 DEG C / min in a tensile mode of a dynamic viscoelasticity measuring apparatus (DMS-6100: manufactured by SAI Co., Ltd.) Was obtained as a glass transition temperature. The results are shown in Table 1.
[투습도][Water vapor permeability]
실시예 및 비교예에서 제조된 액정 시일제를 폴리에틸렌테레프탈레이트(PET) 필름에 끼워 넣어 두께 100㎛의 박막으로 한 것에 UV 조사기에 의해 3000mJ/㎠의 자외선을 조사 후, 오븐에 투입하여 120℃ 40분간 열 경화시키고, 경화 후 PET 필름을 벗겨 샘플로 했다. 샘플의 60℃ 90%에서의 투습도를 투습도 측정기(Lessy사 제조: L80-5000)로 측정했다. 결과를 표 1에 나타낸다.The liquid crystal sealant prepared in Examples and Comparative Examples was sandwiched by a polyethylene terephthalate (PET) film to form a thin film having a thickness of 100 탆. Ultraviolet rays of 3000 mJ / cm 2 were irradiated by a UV irradiator, And the PET film was peeled off after curing to obtain a sample. The moisture permeability at 60 DEG C and 90% of the sample was measured with a moisture permeability meter (L80-5000 manufactured by Lessy Co.). The results are shown in Table 1.
표 1의 결과에서, 본 발명의 디스플레이용 봉지제는, 접착 강도가 높고, 또한 저투습성이라는 특성의 양립을 실현하고 있다. 특히 실시예 1에서는 유리 전이 온도도 높고, 장기 고신뢰성에 있어서도 유리하다고 생각된다.From the results shown in Table 1, the display encapsulant of the present invention realizes both of the characteristics of high adhesive strength and low moisture permeability. In particular, in Example 1, the glass transition temperature is also high and it is considered to be advantageous also in long-term high reliability.
본 발명의 디스플레이용 봉지제는, 피착체와의 접착 강도가 우수하고, 또한 저투습성을 양립하고 있기 때문에, 특히 유기막과의 접착성이 요구되는 디스플레이나 플렉시블 디스플레이, 만곡 형상의 디스플레이용 봉지제로서 유용하다.INDUSTRIAL APPLICABILITY The display encapsulant for display of the present invention is excellent in adhesion strength to an adherend and low in moisture permeability. Therefore, it is particularly preferable to provide a display, a flexible display, a curved display encapsulant .
Claims (9)
을 함유하는 디스플레이용 봉지제.(A) a curing compound having three or more bisphenol skeletons and at least three reactive functional groups in the molecule
≪ / RTI >
상기 성분 (A)의 비스페놀 골격 내(內) 2개 이상이 비스페놀 A 골격인 디스플레이용 봉지제.The method according to claim 1,
Wherein at least two bisphenol A skeletons of the component (A) are bisphenol A skeletons.
상기 성분 (A)의 중량 평균 분자량이 1000 이상인 디스플레이용 봉지제.The method according to claim 1,
Wherein the component (A) has a weight average molecular weight of 1000 or more.
상기 성분 (A)의 반응성 관능기 내 2개 이상이 (메타)아크릴로일기인 디스플레이용 봉지제.The method according to claim 1,
Wherein at least two of the reactive functional groups of the component (A) are (meth) acryloyl groups.
추가로, (B) 경화성 화합물을 함유하는 디스플레이용 봉지제.The method according to claim 1,
Further, a sealing agent for a display containing (B) a curable compound.
상기 성분 (B)가, (B-1) (메타)아크릴 화합물인 디스플레이용 봉지제.6. The method of claim 5,
Wherein the component (B) is a (meth) acrylic compound (B-1).
상기 성분 (B)가, (B-1) (메타)아크릴 화합물과 (B-2) 에폭시 화합물의 혼합물인 디스플레이용 봉지제.6. The method of claim 5,
Wherein the component (B) is a mixture of (B-1) a (meth) acrylic compound and (B-2) an epoxy compound.
추가로, (C) 유기 필러, (D) 무기 필러, (E) 실란 커플링제, (F) 열 경화제, (G) 광 라디칼 중합 개시제 및 (H) 열 라디칼 중합 개시제로 이루어지는 군으로부터 선택되는 적어도 1종을 함유하는 디스플레이용 봉지제.8. The method according to any one of claims 1 to 7,
(C) an organic filler, (D) an inorganic filler, (E) a silane coupling agent, (F) a thermosetting agent, (G) a photo radical polymerization initiator, and (H) a thermal radical polymerization initiator. 1 < / RTI >
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