JP6087824B2 - 液晶シール剤及びそれを用いた液晶表示セル - Google Patents
液晶シール剤及びそれを用いた液晶表示セル Download PDFInfo
- Publication number
- JP6087824B2 JP6087824B2 JP2013536327A JP2013536327A JP6087824B2 JP 6087824 B2 JP6087824 B2 JP 6087824B2 JP 2013536327 A JP2013536327 A JP 2013536327A JP 2013536327 A JP2013536327 A JP 2013536327A JP 6087824 B2 JP6087824 B2 JP 6087824B2
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- JP
- Japan
- Prior art keywords
- liquid crystal
- component
- ether
- crystal sealant
- sealant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 164
- 239000000565 sealant Substances 0.000 title claims description 94
- 229920003986 novolac Polymers 0.000 claims description 44
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 39
- 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 claims description 32
- 238000007789 sealing Methods 0.000 claims description 28
- 239000003822 epoxy resin Substances 0.000 claims description 25
- 229920000647 polyepoxide Polymers 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000007822 coupling agent Substances 0.000 claims description 9
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- 229910003475 inorganic filler Inorganic materials 0.000 claims description 9
- 229920000058 polyacrylate Polymers 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000010410 layer Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 6
- 229940116423 propylene glycol diacetate Drugs 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 5
- 239000012792 core layer Substances 0.000 claims description 5
- 239000011258 core-shell material Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 4
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- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
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- -1 Polyphenol compounds Chemical class 0.000 description 35
- 229920005989 resin Polymers 0.000 description 29
- 239000011347 resin Substances 0.000 description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
- 210000004027 cell Anatomy 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- 239000011521 glass Substances 0.000 description 23
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 19
- 150000002989 phenols Chemical class 0.000 description 18
- 239000000853 adhesive Substances 0.000 description 16
- 230000001070 adhesive effect Effects 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 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 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 150000001896 cresols Chemical class 0.000 description 9
- 239000004210 ether based solvent Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000005259 measurement Methods 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 150000004780 naphthols Chemical class 0.000 description 7
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical class CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 6
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000007650 screen-printing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 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
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 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 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 3
- QCBSYPYHCJMQGB-UHFFFAOYSA-N 2-ethyl-1,3,5-triazine Chemical compound CCC1=NC=NC=N1 QCBSYPYHCJMQGB-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 210000002858 crystal cell Anatomy 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000005350 fused silica glass Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
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- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-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
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 1
- IUGPRERXXKWPFI-UHFFFAOYSA-N 1,2-di(propan-2-yloxy)propane Chemical compound CC(C)OCC(C)OC(C)C IUGPRERXXKWPFI-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- FBRVKWOJAIUGKE-UHFFFAOYSA-N [3-methyl-3-(2-methylpropoxy)butyl] acetate Chemical compound CC(C)COC(C)(C)CCOC(C)=O FBRVKWOJAIUGKE-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- VYGUBTIWNBFFMQ-UHFFFAOYSA-N [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O Chemical group [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O VYGUBTIWNBFFMQ-UHFFFAOYSA-N 0.000 description 1
- UMHKOAYRTRADAT-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] octyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OP(O)(=O)OCCCCCCCC UMHKOAYRTRADAT-UHFFFAOYSA-N 0.000 description 1
- OHBRHBQMHLEELN-UHFFFAOYSA-N acetic acid;1-butoxybutane Chemical compound CC(O)=O.CCCCOCCCC OHBRHBQMHLEELN-UHFFFAOYSA-N 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- UHVCSNKHFBQKBO-UHFFFAOYSA-N benzyl-ethenyl-[2-(3-trimethoxysilylpropylamino)ethyl]azanium;chloride Chemical compound Cl.CO[Si](OC)(OC)CCCNCCN(C=C)CC1=CC=CC=C1 UHVCSNKHFBQKBO-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- UBPGILLNMDGSDS-UHFFFAOYSA-N diethylene glycol diacetate Chemical compound CC(=O)OCCOCCOC(C)=O UBPGILLNMDGSDS-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XMQYIPNJVLNWOE-UHFFFAOYSA-N dioctyl hydrogen phosphite Chemical compound CCCCCCCCOP(O)OCCCCCCCC XMQYIPNJVLNWOE-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- IFZUFHWISBKFJP-UHFFFAOYSA-N n'-[4-[dimethoxy(methyl)silyl]oxybutyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)OCCCCNCCN IFZUFHWISBKFJP-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
-
- 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
-
- 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
- G02F2202/00—Materials and properties
- G02F2202/28—Adhesive materials or arrangements
Landscapes
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Epoxy Resins (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Liquid Crystal (AREA)
Description
例えば、特許文献1には接着性、耐湿信頼性、可撓性に優れる熱硬化型液晶シール剤が開示されている。
特許文献2には接着性、耐湿信頼性、可撓性、熱硬化性に優れる熱硬化型液晶シール剤が開示されている。
特許文献3にはスクリーン印刷性、耐湿信頼性に優れる熱硬化型液晶シール剤が開示されている。
1)
(a)軟化点が75℃以下の固形フェノールノボラック樹脂、(b)コアシェル構造を有するアクリル重合体、(c)エポキシ樹脂、及び(d)有機溶剤を含有し、150℃でのゲルタイムが50秒以上200秒以下である液晶シール剤。
2)
上記成分(b)のコア層がn−ブチルアクリレートの重合体であり、シェル層がメチルメタクリレートの重合体である上記1)に記載の液晶シール剤。
3)
上記成分(d)が、プロピレングリコールジアセテート、二塩基酸ジメチルエステル、プロピレングリコールモノエチルエーテルアセテート、及びエチレングリコールジブチルエーテルからなる群から選択される1種以上の有機溶剤である上記1)又は2)に記載の液晶シール剤。
4)
上記成分(a)が、下記式(1)で表される化合物である上記1)乃至3)のいずれか一項に記載の液晶シール剤。
5)
上記成分(c)のエポキシ基1当量に対する上記成分(a)の水酸基の当量が0.2〜1.4化学当量である上記1)乃至4)のいずれか一項に記載の液晶シール剤。
6)
上記成分(c)が、ビスフェノールA型エポキシ樹脂である上記1)乃至5)のいずれか一項に記載の液晶シール剤。
7)
更に、(e)硬化促進剤を含有する上記1)乃至6)のいずれか一項に記載の液晶シール剤。
8)
上記成分(e)が、2,4−ジアミノ−6−[2’−メチルイミダゾリル−(1’)]−エチル−s−トリアジンイソシアヌル酸付加物及びエポキシ樹脂アミンアダクトから選ばれる少なくとも1種である上記7)に記載の液晶シール剤。
9)
更に、(f)カップリング剤を含有する上記1)乃至8)のいずれか一項に記載の液晶シール剤。
10)
上記成分(f)が、エポキシシランカップリング剤である上記9)に記載の液晶シール剤。
11)
更に、(g)無機充填剤を含有する上記1)乃至10)のいずれか一項に記載の液晶シール剤。
12)
上記1)乃至11)のいずれか一項に記載の液晶シール剤を硬化して得られる硬化物でシールされた液晶表示セル。
なお、本明細書において、メタ(アクリレート)とは、アクリレート及びメタクリレートの一方又は両方を意味する。
有機溶剤の沸点は150〜230℃の範囲が望ましい。沸点が150℃より低いと液晶シール剤スクリーン印刷時の粘度増加が大きく、使用時間が短くなってしまう。沸点が230℃よりも高いと溶剤乾燥時に溶剤が揮発せず、本硬化後の液晶シール剤に気泡が噛みこんだり、硬化物性が低下したりする。
下記表1に示す割合で各樹脂成分(成分(a)、成分(c))及び有機溶剤(成分(d))を混合し、加熱溶解した。室温まで冷却後、必要に応じてカップリング剤(成分(f)、無機充填剤(成分(g))等を適宜添加し、コアシェル構造を有するアクリル重合体(成分(b))、必要に応じて硬化促進剤(成分(e))を添加し、3本ロールにて均一に混合し金属メッシュで濾過し、実施例1〜8、比較例1〜4の液晶シール剤を調製した。
自動ゲル化テスタ(伊予電子製)を使用し、測定温度150℃雰囲気下にて、調製した液晶シール剤を測定部に0.4mL入れ、取り付けたテフロン(登録商標)製ニードルを自転部100rpmにて回転させてシール剤を撹拌し、トルクセンサーが70gcmのトルクを検出するまでの時間をゲルタイムとした。結果を表1に示す。
E型粘度計(VISCONIC EHD型、コーン3°×R14:東京精機株式会社製)にて25℃、10rpmの粘度を測定した。結果を表1に示す。
E型粘度計(VISCONIC EHD型、コーン3°×R14:東京精機株式会社製)にて25℃での、10rpm及び1rpmの粘度を測定し、1rpmの粘度/10rpmの粘度の値をチクソ比とした。結果を表1に示す。
調製した液晶シール剤を25℃雰囲気に48時間保管したものをE型粘度計(VISCONIC EHD型、コーン3°×R14:東京精機株式会社製)にて25℃、10rpmの粘度を測定し、初期粘度からの増粘度を算出し、48時間後の増粘率とした。計算式は、{(48時間後の粘度−初期粘度)/(初期粘度)}×100とした。結果を表1に示す。
洗浄した1.5cm×3cmのITO膜付きガラス基板に、5μmのガラスファイバー(PF−50S:日本電気硝子株式会社製)を液晶シール剤に対して1質量%添加した液晶シール剤を、5μmの厚さに潰したときの直径が0.8〜1.2mmになるように塗布した。90℃設定のホットプレートにて10分間予備加熱を行い、対向基板として、洗浄した1.5cm×3cmのITO膜付きガラス基板をITO面側が液晶シール剤側になるように、十字の形にて貼り合わせ、バインダークリップNo.155(ライオン事務機器製)にて2箇所をとめ、基板を固定させた。150℃設定の電気乾燥機にこの試験片を投入し、室温まで冷却した。ボンドテスター(SS−30WD:西進商事製)の引っ張りモードにて3.3mm/秒の速度にて引っ張り方向の強度を測定した。強度をシールの単位面積当たりに換算し、接着強度とした。評価の基準は以下による。結果を表1に示す。
○・・・接着強度が16MPa以上
△・・・接着強度が10MPa以上16MPa未満
×・・・接着強度が10MPa未満
上記[接着性テスト]と同様の手順にて、試験片の作成を行った。その後60℃90%に設定した恒温恒湿槽(HPAV−80−20:いすゞ製作所製)に12時間投入後、室温にて冷却したものを測定用試験片とした。ボンドテスター(西進商事製SS−30WD)の引っ張りモードにて3.3mm/秒の速度にて引っ張り方向の強度を測定した。強度をシールの単位面積当たりに換算し、耐湿接着強度とした。評価の基準は以下による。結果を表1に示す。
○・・・耐湿接着強度が16MPa以上
△・・・耐湿接着強度が10MPa以上16MPa未満
×・・・耐湿接着強度が10MPa未満
5cm×5cmのガラス基板上に注入口付きのパターンで液晶シール剤をディスペンサーにて断面積5000μm2になるように塗布し、90℃設定の電気乾燥機にて10分間溶剤乾燥(プリキュア)を行った。基板を室温雰囲気まで冷却後、5cm×5cmの対向ガラス基板を重ね合わせ、10kgの錘を30秒間のせ、液晶シール剤の潰れ性を光学顕微鏡にて観察し、液晶シール剤の幅を測定した。測定は液晶シール剤を塗布したガラス基板側と、対向基板の2方向から行い、液晶シール剤を塗布した側の液晶シール剤の幅と、対向基板側の液晶シール剤の幅との比較によって、どの程度潰れているかを評価した。評価の基準は以下による。結果を表1に示す。
◎・・・対向ガラス基板の幅が液晶シール剤を塗布した基板の幅の70%以上
○・・・対向ガラス基板の幅が液晶シール剤を塗布した基板の幅の40%以上70%未満
△・・・対向ガラス基板の幅が液晶シール剤を塗布した基板の幅の10%以上40%未満
×・・・対向ガラス基板の幅が液晶シール剤を塗布した基板の幅の10%未満あるいは全く接していない
5cm×5cmのガラス基板上に注入口付きのパターンで液晶シール剤をディスペンサーにて断面積5000μm2になるように塗布し、90℃設定の電気乾燥機にて10分間溶剤乾燥(プリキュア)を行った。基板を室温雰囲気まで冷却後、5cm×5cmの対向ガラス基板を重ね合わせ、4辺をバインダークリップNo.155(ライオン事務機器製)にて挟み、150℃設定の電気乾燥器にて60分間投入した。基板を室温まで冷却後基板の液晶シール剤の様子を光学顕微鏡にて観察した。本試験においては、硬化性等の影響から、樹脂成分の染み出しの有無(樹脂成分とフィラー成分の相分離の有無)を確認する。評価の基準は以下による。結果を表1に示す。
○・・・樹脂成分の染み出しが無い
×・・・樹脂成分の染み出しが有る
調製した液晶シール剤を、スクリーン印刷機(LS−150:ニューロング精密工業株式回社製)にてガラス基板に印刷塗布した。これを目視にて確認した。かすれ、液晶シール剤の切れ等の有無を観察した。評価の基準は以下による。結果を表1に示す。
○・・・かすれ、切れが無い
×・・・かすれ、切れが有る
調製した液晶シール剤をシリンジに充填・脱泡した後、ディスペンサー(ショットマスター300:武蔵エンジニアリング社製)にてガラス基板上に30mm/secで塗布し、形状を目視にて確認した。かすれ、液晶シール剤の切れ等の有無を観察した。評価の基準は以下による。結果を表1に示す。
○・・・かすれ、切れが無い
×・・・かすれ、切れが有る
10mLサンプル瓶の底に調製した液晶シール剤を100mg程度均一に塗布した後、90℃に設定した電気乾燥機にて10分間溶剤乾燥(プリキュア)を行った。その後150℃に設定した電気乾燥機にて60分硬化した。室温に冷却後、液晶(MLC−6866−100:メルク株式会社製)を液晶シール剤の10倍量加えた。90℃設定の電気乾燥機にて24時間加熱した後、30分間冷却した。それぞれの上澄みをデカンテーションにて分け取り、デジタル超高抵抗計(R8340:株式会社アドバンテスト製)にて比抵抗値を測定した。評価の基準は以下による。結果を表1に示す。
○・・・比抵抗値が1.0×10E+12以上
×・・・比抵抗値が1.0×10E+12未満
なお、比抵抗値の「1.0E+12」は「1.0×1012」を表し、他の記載も同様である。
5cm×7cmのガラス基板上に調製した液晶シール剤を25μmのクリアランスのアプリケーターを使用して塗布した。90℃に設定した電気乾燥機にて10分間溶剤乾燥を行い、150℃に設定した電気乾燥機にて60分間硬化させた。60℃90%に設定した恒温恒湿槽(HPAV−80−20:いすゞ製作所)に24時間投入後室温にて冷却した液晶シール剤と硬化直後の液晶シール剤との重量変化から吸水率を算出した。算出式は{(吸水後のシール剤重量−吸水前のシール剤重量)/(吸水前のシール剤重量)}×100とした。結果を表1に示す。
したがって、本発明の液晶シール剤は、工程を通じて作業性に問題がなく、信頼性に非常に優れたシール剤であるといえる。
Claims (11)
- (a)軟化点が75℃以下の固形フェノールノボラック樹脂、(b)コア層がn−ブチルアクリレートの重合体であり、シェル層がメチルメタクリレートの重合体であるコアシェル構造を有するアクリル重合体、(c)エポキシ樹脂、及び(d)有機溶剤を含有し、150℃でのゲルタイムが50秒以上200秒以下である液晶シール剤。
- 前記成分(d)が、プロピレングリコールジアセテート、二塩基酸ジメチルエステル、プロピレングリコールモノエチルエーテルアセテート、及びエチレングリコールジブチルエーテルからなる群から選択される1種以上の有機溶剤である請求項1に記載の液晶シール剤。
- 前記成分(a)が、下記式(1)で表される化合物である請求項1又は2に記載の液晶シール剤。
- 前記成分(c)のエポキシ基1当量に対する前記成分(a)の水酸基の当量が0.2〜1.4化学当量である請求項1乃至3のいずれか一項に記載の液晶シール剤。
- 前記成分(c)が、ビスフェノールA型エポキシ樹脂である請求項1乃至4のいずれか一項に記載の液晶シール剤。
- 更に、(e)硬化促進剤を含有する請求項1乃至5のいずれか一項に記載の液晶シール剤。
- 前記成分(e)が、2,4−ジアミノ−6−[2’−メチルイミダゾリル−(1’)]−エチル−s−トリアジンイソシアヌル酸付加物及びエポキシ樹脂アミンアダクトから選ばれる少なくとも1種である請求項6に記載の液晶シール剤。
- 更に、(f)カップリング剤を含有する請求項1乃至7のいずれか一項に記載の液晶シール剤。
- 前記成分(f)が、エポキシシランカップリング剤である請求項8に記載の液晶シール剤。
- 更に、(g)無機充填剤を含有する請求項1乃至9のいずれか一項に記載の液晶シール剤。
- 請求項1乃至10のいずれか一項に記載の液晶シール剤を硬化して得られる硬化物でシールされた液晶表示セル。
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