CN117203577A - Sealing agent for liquid crystal display element and liquid crystal display element - Google Patents
Sealing agent for liquid crystal display element and liquid crystal display element Download PDFInfo
- Publication number
- CN117203577A CN117203577A CN202280030400.XA CN202280030400A CN117203577A CN 117203577 A CN117203577 A CN 117203577A CN 202280030400 A CN202280030400 A CN 202280030400A CN 117203577 A CN117203577 A CN 117203577A
- Authority
- CN
- China
- Prior art keywords
- liquid crystal
- meth
- crystal display
- display element
- present
- 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.)
- Pending
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 118
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 39
- 238000007789 sealing Methods 0.000 title abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 239000000565 sealant Substances 0.000 claims abstract description 81
- 229920005989 resin Polymers 0.000 claims abstract description 80
- 239000011347 resin Substances 0.000 claims abstract description 80
- 239000004593 Epoxy Substances 0.000 claims abstract description 69
- -1 (meth) acrylic acid modified bisphenol Chemical class 0.000 claims abstract description 55
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 27
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 11
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 6
- 230000035699 permeability Effects 0.000 abstract description 22
- 230000002265 prevention Effects 0.000 abstract description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 21
- 239000010936 titanium Substances 0.000 description 21
- 229910052719 titanium Inorganic materials 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 239000010419 fine particle Substances 0.000 description 12
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000011109 contamination Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 230000002542 deteriorative effect Effects 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- ZNGSVRYVWHOWLX-KHFUBBAMSA-N (1r,2s)-2-(methylamino)-1-phenylpropan-1-ol;hydrate Chemical compound O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 ZNGSVRYVWHOWLX-KHFUBBAMSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 1
- LOCXTTRLSIDGPS-FVDSYPCUSA-N [(z)-[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(/CCCCCC)=N\OC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-FVDSYPCUSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
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- 230000002411 adverse Effects 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
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- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
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- 239000007822 coupling agent Substances 0.000 description 1
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical compound [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
- 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 1
- 239000006185 dispersion Substances 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
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- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 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
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 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
- 238000004513 sizing Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/106—Esters of polycondensation macromers
- C08F222/1067—Esters of polycondensation macromers of alcohol terminated epoxy functional polymers, e.g. epoxy(meth)acrylates
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
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- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
- C08F299/024—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0625—Polyacrylic esters or derivatives thereof
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
- C09K2200/0647—Polyepoxides
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- Chemical & Material Sciences (AREA)
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- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal (AREA)
- Sealing Material Composition (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The purpose of the present invention is to provide a sealing agent for a liquid crystal display element, which has excellent adhesion, moisture permeability resistance and wall adhesion prevention performance in a syringe. The present invention also provides a liquid crystal display element using the sealant for a liquid crystal display element. The sealant for a liquid crystal display element of the present invention contains a curable resin, a radical polymerization initiator, and a thermosetting agent, and the curable resin contains: (A) A partially (meth) acrylic-modified epoxy compound having 3 or more aromatic rings in 1 molecule; (B) At least 1 selected from bisphenol a type epoxy (meth) acrylate, bisphenol F type epoxy (meth) acrylate, bisphenol E type epoxy (meth) acrylate, a partially (meth) acrylic acid modified bisphenol a type epoxy compound, a partially (meth) acrylic acid modified bisphenol F type epoxy compound, and a partially (meth) acrylic acid modified bisphenol E type epoxy compound; and (C) a (meth) acrylic compound having a molecular weight of 100 to 300.
Description
Technical Field
The present invention relates to a sealant for a liquid crystal display element, which has excellent adhesion, moisture permeability resistance, and wall sticking prevention performance in a syringe. The present invention also relates to a liquid crystal display element using the sealant for a liquid crystal display element.
Background
In recent years, as a method for manufacturing a liquid crystal display element such as a liquid crystal display cell, a liquid crystal dropping method called a dropping method using a sealant as disclosed in patent document 1 and patent document 2 has been used from the viewpoints of shortening the tact time and optimizing the amount of liquid crystal used.
In the dropping process, first, a frame-shaped seal pattern is formed on one of two substrates with electrodes by dispensing. Next, a liquid crystal display element was fabricated by dropping a droplet of liquid crystal into a sealing frame of a substrate in a state where the sealant was not cured, and by superposing another substrate under vacuum, curing the sealant. Currently, the dropping process is the mainstream of a method for manufacturing a liquid crystal display element.
However, in modern times, in which various mobile devices with liquid crystal panels such as mobile phones and portable game machines are used, miniaturization of the device is the most desirable task. As a method of downsizing, for example, a liquid crystal display portion is narrowed, and a sealing portion is arranged below a black matrix (hereinafter, also referred to as "narrow frame design").
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2001-133794
Patent document 2: international publication No. 02/092718
Disclosure of Invention
Problems to be solved by the invention
With the narrow frame design, in the liquid crystal display element, the distance from the pixel region to the sealant becomes short, and display unevenness due to contamination of the liquid crystal with the sealant is liable to occur.
In addition, with the spread of flat-panel terminals and portable terminals, a liquid crystal display element is increasingly required to have moisture-proof reliability in driving under a high-temperature and high-humidity environment and the like, and a sealant is further required to have a performance of preventing water from entering from the outside. Therefore, it is necessary to improve the moisture permeability resistance of the sealant, but as the width of the line of the applied sealant becomes smaller with a narrow frame design, it is difficult to obtain a sealant excellent in moisture permeability resistance even in the case of thinning.
The purpose of the present invention is to provide a sealing agent for a liquid crystal display element, which has excellent adhesion, moisture permeability resistance and wall adhesion prevention performance in a syringe. The present invention also provides a liquid crystal display element using the sealant for a liquid crystal display element.
Means for solving the problems
The present invention 1 is a sealant for a liquid crystal display element, comprising a curable resin, a radical polymerization initiator, and a thermosetting agent, wherein the curable resin comprises: (A) A partially (meth) acrylic-modified epoxy compound having 3 or more aromatic rings in 1 molecule; (B) At least 1 selected from bisphenol a type epoxy (meth) acrylate, bisphenol F type epoxy (meth) acrylate, bisphenol E type epoxy (meth) acrylate, a partially (meth) acrylic acid modified bisphenol a type epoxy compound, a partially (meth) acrylic acid modified bisphenol F type epoxy compound, and a partially (meth) acrylic acid modified bisphenol E type epoxy compound; and (C) a (meth) acrylic compound having a molecular weight of 100 to 300.
The present invention 2 is a sealant for a liquid crystal display element according to the present invention 1, wherein the (meth) acrylic compound having a molecular weight of 100 or more and 300 or less is a monofunctional (meth) acrylic compound having only 1 (meth) acryloyl group in 1 molecule.
The invention 3 is a sealant for a liquid crystal display element according to the invention 1 or 2, wherein the content of the (meth) acrylic compound having a molecular weight of 100 to 300 in 100 parts by weight of the entire curable resin is 0.1 to 10 parts by weight.
The invention 4 is a liquid crystal display element comprising the cured product of the sealant for a liquid crystal display element according to the invention 1,2 or 3.
The present invention will be described in detail below.
The present inventors have conducted the following studies: the use of a partially (meth) acrylic-modified epoxy compound having 3 or more aromatic rings in 1 molecule as a curable resin improves the moisture permeability resistance of a sealant for a liquid crystal display element. In order to secure adhesion, further use of bisphenol a type epoxy (meth) acrylate or the like as a curable resin has been studied. However, when the obtained sealant for a liquid crystal display element is filled into a syringe for dispensing and used continuously, there is a problem that the wall of the sealant for a liquid crystal display element is easily formed in the syringe. Accordingly, the present inventors have conducted intensive studies and as a result, have found that a sealing agent for a liquid crystal display element excellent in adhesion, moisture permeation resistance and wall sticking prevention performance in a syringe can be obtained by further using a (meth) acrylic compound having a molecular weight of 100 to 300, and have completed the present invention.
The sealant for a liquid crystal display element of the present invention contains a curable resin.
The curable resin contains (a) a partially (meth) acrylic-modified epoxy compound having 3 or more aromatic rings in 1 molecule (hereinafter, also referred to as "curable resin a of the present invention"). By containing the curable resin a of the present invention, the sealant for a liquid crystal display element of the present invention is excellent in moisture permeability resistance.
In the present specification, the term "(meth) acrylic" means acrylic or methacrylic. The "partially (meth) acrylic-modified epoxy compound" means a compound obtained by reacting a part of epoxy groups of an epoxy compound having 2 or more epoxy groups in 1 molecule with (meth) acrylic acid, and having 1 or more epoxy groups and (meth) acryloyl groups in 1 molecule. Further, the "(meth) acryl" mentioned above means acryl or methacryl.
The curable resin A of the present invention has 3 or more aromatic rings in 1 molecule. By using the curable resin a of the present invention having 3 or more aromatic rings in 1 molecule, the sealant for a liquid crystal display element of the present invention is excellent in moisture permeability resistance even when it is applied in a thin line. By increasing the number of aromatic rings in the curable resin a of the present invention, both moisture permeability and adhesion of the cured product of the obtained sealant for a liquid crystal display element can be achieved.
In addition, from the viewpoint of coatability and the like, the curable resin a of the present invention preferably has 5 or less aromatic rings in 1 molecule.
The aromatic ring of the curable resin a of the present invention may be an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
Specific examples of the aromatic ring included in the curable resin a of the present invention include benzene ring, naphthalene ring, anthracene ring, and furan ring. Among them, benzene rings are preferable.
The lower limit of the molecular weight of the curable resin a of the present invention is preferably 300, and the upper limit is preferably 600. The curable resin a of the present invention has a molecular weight of 300 or more, and thus the sealant for a liquid crystal display element of the present invention is more excellent in low liquid crystal contamination. The curable resin a of the present invention has a molecular weight of 600 or less, and thus the sealant for a liquid crystal display element of the present invention is more excellent in coatability. The lower limit of the molecular weight of the curable resin a of the present invention is more preferably 400, and the upper limit is more preferably 500.
In the present specification, the "molecular weight" is a molecular weight obtained from a structural formula of a compound having a defined molecular structure, but may be represented by a weight average molecular weight of a compound having a broad distribution of polymerization degrees and a compound having an indefinite modification site.
In the present specification, the "weight average molecular weight" is a value obtained by measuring by Gel Permeation Chromatography (GPC) using tetrahydrofuran as a solvent and converting the obtained product into polystyrene. Examples of the column used for measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa electric company).
Specifically, the curable resin a of the present invention is preferably a compound represented by the following formulas (1-1) to (1-6), more preferably a compound represented by the following formula (1-5).
[ chemical formula 1]
In the formulae (1-1) to (1-6), R represents a hydrogen atom or a methyl group.
The curable resin a of the present invention can be produced, for example, by reacting a part of epoxy groups of a diepoxy compound having 3 or more aromatic rings in 1 molecule with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
Examples of the above-mentioned diepoxy compound having 3 or more aromatic rings in 1 molecule include diglycidyl ether having 3 or more aromatic rings in 1 molecule, and the like, preferably compounds represented by the following formulas (2-1) to (2-6), and more preferably compounds represented by the following formula (2-5).
[ chemical formula 2]
The lower limit of the content of the curable resin a of the present invention in 100 parts by weight of the curable resin is preferably 15 parts by weight, and the upper limit is preferably 60 parts by weight. The content of the curable resin a of the present invention is 15 parts by weight or more, and the obtained sealant for a liquid crystal display element is more excellent in moisture permeability. The content of the curable resin a of the present invention is 60 parts by weight or less, and the resulting sealant for a liquid crystal display element is more excellent in adhesion and wall sticking prevention performance in a syringe. The lower limit of the content of the curable resin a of the present invention is more preferably 30 parts by weight, and the upper limit is more preferably 50 parts by weight.
The curable resin contains (B) at least 1 selected from the group consisting of bisphenol a epoxy (meth) acrylate, bisphenol F epoxy (meth) acrylate, bisphenol E epoxy (meth) acrylate, partially (meth) acrylic acid-modified bisphenol a epoxy compound, partially (meth) acrylic acid-modified bisphenol F epoxy compound, and partially (meth) acrylic acid-modified bisphenol E epoxy compound (hereinafter, also referred to as "curable resin B of the present invention"). By containing the curable resin B of the present invention, the sealing agent for a liquid crystal display element of the present invention is excellent in adhesion and the like. Among them, bisphenol a type epoxy (meth) acrylate is preferable as the curable resin B of the present invention.
In the present specification, the term "(meth) acrylate" means an acrylate or a methacrylate, and the term "epoxy (meth) acrylate" means a compound obtained by reacting all epoxy groups in an epoxy compound with (meth) acrylic acid.
In addition, even in the case of the partial (meth) acrylic acid-modified bisphenol a-type epoxy compound, the partial (meth) acrylic acid-modified bisphenol F-type epoxy compound, and the partial (meth) acrylic acid-modified bisphenol E-type epoxy compound, a compound having 3 or more aromatic rings in 1 molecule is treated not as the curable resin B of the present invention but as the curable resin a of the present invention.
The lower limit of the molecular weight of the curable resin B of the present invention is preferably 200, and the upper limit is preferably 1600. The curable resin B of the present invention has a molecular weight of 200 or more, and thus the sealant for a liquid crystal display element of the present invention is more excellent in low liquid crystal contamination. The curable resin B of the present invention has a molecular weight of 1600 or less, and thus the sealant for a liquid crystal display element of the present invention is more excellent in coatability. The lower limit of the molecular weight of the curable resin B of the present invention is more preferably 300, and the upper limit is more preferably 500.
The preferable lower limit of the content of the curable resin B of the present invention in 100 parts by weight of the curable resin is 40 parts by weight, and the preferable upper limit is 75 parts by weight. The content of the curable resin B of the present invention is 40 parts by weight or more, and the resulting sealant for a liquid crystal display element is more excellent in adhesion. The content of the curable resin B of the present invention is 75 parts by weight or less, and the obtained sealant for a liquid crystal display element is further excellent in moisture permeability. The lower limit of the content of the curable resin B of the present invention is more preferably 45 parts by weight, and the upper limit is more preferably 65 parts by weight.
The curable resin contains (C) a (meth) acrylic compound having a molecular weight of 100 to 300 (hereinafter, also referred to as "curable resin C" of the present invention). By containing the curable resin C of the present invention, the sealant for a liquid crystal display element of the present invention is excellent in the prevention of sticking to a wall in a syringe.
In the present specification, the "(meth) acrylic compound" means a compound having a (meth) acryloyl group.
Further, even if the molecular weight is 100 or more and 300 or less, the curable resin C of the present invention is not treated as the curable resin a of the present invention, as long as it is a partially (meth) acrylic-modified epoxy compound having 3 or more aromatic rings in 1 molecule.
Further, even if the molecular weight is 100 or more and 300 or less, it is not treated as the curable resin C of the present invention but as the curable resin B of the present invention as long as it is at least 1 selected from bisphenol a type epoxy (meth) acrylate, bisphenol F type epoxy (meth) acrylate, bisphenol E type epoxy (meth) acrylate, partially (meth) acrylic acid modified bisphenol a type epoxy compound, partially (meth) acrylic acid modified bisphenol F type epoxy compound and partially (meth) acrylic acid modified bisphenol E type epoxy compound.
The curable resin C of the present invention has a molecular weight of 100 as a lower limit and 300 as an upper limit. When the molecular weight of the curable resin C of the present invention is in this range, the sealant for a liquid crystal display element of the present invention is excellent in the prevention of wall sticking in a syringe. The curable resin C of the present invention has a preferable lower limit of 120, a more preferable lower limit of 140, a preferable upper limit of 250, and a more preferable upper limit of 220.
The curable resin C of the present invention is preferably a monofunctional (meth) acrylic compound having only 1 (meth) acryloyl group in 1 molecule, from the viewpoint of further excellent performance of preventing wall sticking in a syringe.
Specific examples of the curable resin C of the present invention include phenoxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, isobornyl (meth) acrylate, and 2-hydroxy-3- (meth) acryloxypropyl (meth) acrylate.
The lower limit of the content of the curable resin C of the present invention in 100 parts by weight of the curable resin is preferably 0.1 part by weight, and the upper limit is preferably 10 parts by weight. When the content of the curable resin C in the present invention is 0.1 part by weight or more, the resulting sealant for a liquid crystal display element is more excellent in the prevention of wall sticking in a syringe. The curable resin C of the present invention is contained in an amount of 10 parts by weight or less, whereby the resulting sealant for a liquid crystal display element is more excellent in adhesion and low liquid crystal contamination. The lower limit of the content of the curable resin C of the present invention is more preferably 1 part by weight, the lower limit is more preferably 2 parts by weight, and the upper limit is more preferably 5 parts by weight.
The curable resin may contain other curable resins in addition to the curable resins a to C of the present invention within a range that does not hinder the object of the present invention.
Examples of the other curable resin include an epoxy compound, a partially (meth) acrylic-modified epoxy compound other than the partially (meth) acrylic-modified epoxy compound contained in the curable resin a of the present invention and the curable resin B of the present invention, and an epoxy (meth) acrylate other than the epoxy (meth) acrylate contained in the curable resin B of the present invention.
Examples of the epoxy compound include bisphenol a type epoxy compound, bisphenol F type epoxy compound, bisphenol E type epoxy compound, bisphenol S type epoxy compound, resorcinol type epoxy compound, biphenyl type epoxy compound, thioether type epoxy compound, diphenyl ether type epoxy compound, dicyclopentadiene type epoxy compound, naphthalene type epoxy compound, phenol novolac type epoxy compound, o-cresol novolac type epoxy compound, dicyclopentadiene novolac type epoxy compound, biphenyl novolac type epoxy compound, naphthol novolac type epoxy compound, glycidylamine type epoxy compound, alkyl polyol type epoxy compound, rubber modified type epoxy compound, and glycidyl ester compound.
The sealant for a liquid crystal display element of the present invention contains a radical polymerization initiator.
Examples of the radical polymerization initiator include a photo radical polymerization initiator that generates radicals by irradiation with light, and a thermal radical polymerization initiator that generates radicals by heating.
Examples of the photo-radical polymerization initiator include benzophenone-based compounds, acetophenone-based compounds, acylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin ether-based compounds, and thioxanthone-based compounds.
Specific examples of the photo-radical polymerization initiator include 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, 2- (dimethylamino) -2- ((4-methylphenyl) methyl) -1- (4- (4-morpholinyl) phenyl) -1-butanone, 2-dimethoxy-1, 2-diphenylethane-1-one, bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 1- (4- (2-hydroxyethoxy) -phenyl) -2-hydroxy-2-methyl-1-propan-1-one, 1- (4- (phenylthio) phenyl) -1, 2-octanedione 2- (O-benzoyl oxime), 2,4, 6-trimethylbenzoyl diphenylphosphine oxide, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and the like.
The photo radical polymerization initiator may be used alone or in combination of 2 or more.
Examples of the thermal radical polymerization initiator include thermal radical polymerization initiators composed of azo compounds, organic peroxides, and the like. Among them, an initiator composed of an azo compound (hereinafter, also referred to as "azo initiator") is preferable from the viewpoint of suppressing liquid crystal contamination, and an initiator composed of a polymer azo compound (hereinafter, also referred to as "polymer azo initiator") is more preferable.
The thermal radical polymerization initiator may be used alone or in combination of 2 or more.
In the present specification, the term "polymer azo compound" means a compound having an azo group and having a number average molecular weight of 300 or more, which generates radicals capable of curing a (meth) acryloyl group by heat.
The number average molecular weight of the polymer azo compound is preferably 1000 at the lower limit and 30 tens of thousands at the upper limit. When the number average molecular weight of the polymer azo compound is in this range, adverse effects on the liquid crystal can be prevented and the polymer azo compound can be easily mixed into the curable resin. The number average molecular weight of the polymer azo compound is more preferably limited to 5000, more preferably to 10 ten thousand, still more preferably to 1 ten thousand, and still more preferably to 9 ten thousand.
In the present specification, the number average molecular weight is a value obtained by conversion to polystyrene, measured by Gel Permeation Chromatography (GPC) using tetrahydrofuran as a solvent. Examples of the column used for measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa electric company).
Examples of the polymer azo compound include polymer azo compounds having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via azo groups.
The polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via azo groups is preferably a polymer azo compound having a polyethylene oxide structure.
Specific examples of the polymer azo compound include a polycondensate of 4,4 '-azobis (4-cyanovaleric acid) and polyalkylene glycol, and a polycondensate of 4,4' -azobis (4-cyanovaleric acid) and polydimethylsiloxane having a terminal amino group.
Examples of the commercially available products of the polymeric azo initiator include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (both manufactured by Fuji film and Wako pure chemical industries, ltd.).
Examples of azo initiators other than polymers include V-65 and V-501 (both of Fuji photo-pure chemical Co., ltd.).
Examples of the organic peroxide include ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
The content of the radical polymerization initiator is preferably limited to 0.01 part by weight and the content is preferably limited to 10 parts by weight based on 100 parts by weight of the curable resin. When the content of the radical polymerization initiator is within this range, the resulting sealant for a liquid crystal display element is more excellent in storage stability and curability while suppressing contamination of liquid crystal. The more preferable lower limit of the content of the radical polymerization initiator is 0.1 part by weight, and the more preferable upper limit is 5 parts by weight.
The sealant for a liquid crystal display element of the present invention contains a thermosetting agent.
Examples of the thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, and acid anhydrides. Among them, organic acid hydrazides are suitably used.
The above-mentioned thermosetting agents may be used alone or in combination of 2 or more.
Examples of the organic acid hydrazide include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
Examples of the commercial products of the organic acid hydrazide include organic acid hydrazides manufactured by Otsuka chemical company, and organic acid hydrazides manufactured by Ajinomoto Fine-Techno company.
Examples of the organic acid hydrazide manufactured by Otsuka chemical Co., ltd include SDH, ADH, MDH.
Examples of the organic acid hydrazide manufactured by Ajinomoto Fine-Techno include Amicure VDH, amicure VDH-J, amicure UDH, and Amicure UDH-J.
The content of the thermosetting agent is preferably 1 part by weight at a lower limit and 50 parts by weight at an upper limit, based on 100 parts by weight of the curable resin. When the content of the thermosetting agent is within this range, thermosetting properties can be further improved without deteriorating the coatability, storage stability, and the like of the obtained sealing agent for a liquid crystal display element. The more preferable upper limit of the content of the above-mentioned thermosetting agent is 30 parts by weight.
The sealant for a liquid crystal display element of the present invention preferably contains a filler for the purpose of increasing viscosity, further improving adhesiveness due to a stress dispersion effect, improving linear expansion coefficient, improving moisture resistance of a cured product, and the like.
As the filler, an inorganic filler and an organic filler can be used.
Examples of the inorganic filler include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, montmorillonite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium hydroxide, aluminum nitride, silicon nitride, barium sulfate, and calcium silicate.
Examples of the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles.
The above fillers may be used alone or in combination of 2 or more.
The preferable lower limit of the content of the filler in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is 10 parts by weight, and the preferable upper limit is 70 parts by weight. When the content of the filler is within this range, the effect of improving the adhesion and the like is more excellent without deteriorating the coating property and the like. The lower limit of the content of the filler is more preferably 20 parts by weight, and the upper limit is more preferably 60 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a silane coupling agent. The silane coupling agent mainly has a role as an adhesion promoter for favorably adhering the sealing agent to a substrate or the like.
As the silane coupling agent, for example, 3-aminopropyl trimethoxysilane, 3-mercaptopropyl trimethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-isocyanatopropyl trimethoxysilane and the like are suitably used. These have excellent effect of improving adhesion to a substrate or the like, and can inhibit the outflow of the curable resin into the liquid crystal by chemical bonding with the curable resin.
The silane coupling agent may be used alone or in combination of 2 or more.
The preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is 0.1 part by weight, and the preferable upper limit is 10 parts by weight. When the content of the silane coupling agent is within this range, the occurrence of liquid crystal contamination is suppressed, and the effect of improving the adhesion is more excellent. The more preferable lower limit of the content of the above silane coupling agent is 0.3 parts by weight, and the more preferable upper limit is 5 parts by weight.
The sealant for a liquid crystal display element of the present invention may contain a light shielding agent. By containing the light-shielding agent, the sealant for a liquid crystal display element of the present invention can be suitably used as a light-shielding sealant.
Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Among them, titanium black is preferable.
The titanium black is a substance having a higher transmittance for light in the vicinity of the ultraviolet region, particularly in the range of from 370nm to 450nm, than for light having a wavelength of from 300nm to 800 nm. That is, the titanium black is an opacifier having the following properties: the sealant for a liquid crystal display element of the present invention is provided with light shielding properties by sufficiently shielding light having a wavelength in the visible light range, and is transmitted by light having a wavelength in the vicinity of the ultraviolet range. Therefore, the photocuring property of the sealant for a liquid crystal display element of the present invention can be further increased by using, as the photo radical polymerization initiator, a photo radical polymerization initiator that can initiate a reaction by light having a wavelength (370 nm to 450 nm) at which the transmittance of the titanium black is high. On the other hand, the light-shielding agent contained in the sealant for a liquid crystal display element of the present invention is preferably a material having high insulation properties, and titanium black is also preferable as the light-shielding agent having high insulation properties.
The optical density (OD value) of titanium black per 1 μm is preferably 3 or more, more preferably 4 or more. The higher the light-shielding property of the titanium black, the better, and the preferable upper limit of the OD value of the titanium black is not particularly limited, and is usually 5 or less.
The titanium black exhibits sufficient effects even without surface treatment, but may be used: titanium black surface-treated with an organic component such as a coupling agent, or titanium black surface-treated with an inorganic component such as silica, titania, germania, alumina, zirconia, magnesia, or the like. Among them, titanium black treated with an organic component is preferable in that the insulation property can be further improved.
In addition, since a liquid crystal display element manufactured using the sealant for a liquid crystal display element of the present invention, in which the titanium black is blended as a light shielding agent, has sufficient light shielding properties, a liquid crystal display element having high contrast and excellent image display quality without light leakage can be realized.
Examples of the commercial products of the titanium black include titanium black manufactured by Mitsubishi Materials, titanium black manufactured by red ear formation, and the like.
Examples of the titanium black produced by the company Mitsubishi Materials include 12S, 13M-C, 13R-N, and 14M-C.
Examples of the titanium black produced by the above-mentioned red spike chemical industry include tisack D.
The preferable lower limit of the specific surface area of the titanium black is 13m 2 Per g, a preferred upper limit is 30m 2 With a lower limit of 15m being more preferred per gram 2 A more preferred upper limit is 25m 2 /g。
The preferable lower limit of the volume resistance of the titanium black is 0.5 Ω·cm, the preferable upper limit is 3 Ω·cm, the more preferable lower limit is 1 Ω·cm, and the more preferable upper limit is 2.5 Ω·cm.
The primary particle diameter of the light-shielding agent is not particularly limited as long as it is not more than the distance between substrates of the liquid crystal display element, and is preferably 1nm at a lower limit and 5000nm at an upper limit. When the primary particle diameter of the light-shielding agent is in this range, the light-shielding property can be further improved without deteriorating the coating property and the like of the obtained sealing agent for a liquid crystal display element. The primary particle diameter of the light-shielding agent is more preferably 5nm in lower limit, more preferably 200nm in upper limit, still more preferably 10nm in lower limit, and still more preferably 100nm in upper limit.
The primary particle size of the light-shielding agent may be measured by dispersing the light-shielding agent in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICLE SIZING SYSTEMS).
The lower limit of the content of the light shielding agent in 100 parts by weight of the sealant for a liquid crystal display element of the present invention is preferably 5 parts by weight, and the upper limit is preferably 80 parts by weight. When the content of the light blocking agent is within this range, more excellent light blocking properties can be exhibited without significantly reducing the adhesiveness, strength after curing, and paintability of the obtained sealant for a liquid crystal display element. The content of the light-shielding agent is more preferably 10 parts by weight, still more preferably 70 parts by weight, still more preferably 30 parts by weight, and still more preferably 60 parts by weight.
The sealant for a liquid crystal display element of the present invention may further contain additives such as a stress-relaxing agent, a reactive diluent, a thixotropic agent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, and a polymerization inhibitor, as necessary.
Examples of the method for producing the sealant for a liquid crystal display element of the present invention include a method in which a curable resin, a radical polymerization initiator, a thermosetting agent, and an additive such as a silane coupling agent, which is added as needed, are mixed using a mixer such as a homodispenser, homomixer, universal mixer, planetary mixer, kneader, or three-roll mixer.
By incorporating conductive fine particles into the sealing agent for a liquid crystal display element of the present invention, a vertically conductive material can be produced.
As the conductive fine particles, metal balls, conductive fine particles having a conductive metal layer formed on the surface of the resin fine particles, and the like can be used. Among them, conductive fine particles having a conductive metal layer formed on the surface of the resin fine particles are preferable because the conductive fine particles can be electrically connected without damaging the transparent substrate or the like due to the excellent elasticity of the resin fine particles.
The liquid crystal display element comprising the cured product of the sealant for a liquid crystal display element of the present invention is also one of the present invention.
In addition, as the liquid crystal display element of the present invention, a liquid crystal display element of a narrow frame design is preferable. Specifically, the width of the frame portion around the liquid crystal display portion is preferably 2mm or less.
The width of the sealant for a liquid crystal display element of the present invention applied in the production of the liquid crystal display element of the present invention is preferably 1mm or less.
The sealant for a liquid crystal display element of the present invention can be suitably used for manufacturing a liquid crystal display element by a liquid crystal dropping process. Examples of the method for manufacturing the liquid crystal display element of the present invention by the liquid crystal dropping method include the following methods.
First, the following steps are performed: the sealing agent for a liquid crystal display element of the present invention is applied to a substrate by screen printing, dispenser application, or the like to form a frame-like seal pattern. Next, the following steps were performed: in the uncured state such as the sealant for a liquid crystal display element of the present invention, minute droplets of liquid crystal are applied dropwise to the entire inner surface of the frame of the seal pattern, and the other substrate is immediately superimposed. Then, a liquid crystal display element can be obtained by performing a step of temporarily curing the sealing agent by irradiating the sealing pattern portion with light such as ultraviolet light and a step of final curing the temporarily cured sealing agent by heating.
Effects of the invention
According to the present invention, a sealant for a liquid crystal display element excellent in adhesion, moisture permeability resistance, and wall sticking prevention performance in a syringe can be provided. Further, according to the present invention, a liquid crystal display element using the sealant for a liquid crystal display element can be provided.
Detailed Description
The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
(production of Compound represented by the formula (1-1))
37.4 parts by weight of the compound represented by the above formula (2-1), 0.1 part by weight of p-methoxyphenol as a polymerization inhibitor, 0.1 part by weight of triethylamine as a reaction catalyst, and 7.2 parts by weight of acrylic acid were reflux-stirred at 90℃for 5 hours while introducing air. To adsorb ionic impurities in the reaction product, 100 parts by weight of the obtained reaction product was filtered using a column packed with 10 parts by weight of a natural bond of quartz and kaolin (manufactured by Hoffmann Mineral company, "SILLITIN V"), to obtain a compound represented by the above formula (1-1) (R is a hydrogen atom).
The structure of the compound represented by the above formula (1-1) is obtained by 1 H-NMR、 13 C-NMR and FT-IR.
(production of Compound represented by the formula (1-2))
The same procedure as in the above "(production of a compound represented by the formula (1-1)" was conducted except that 40.2 parts by weight of the compound represented by the formula (2-2) was used instead of 37.4 parts by weight of the compound represented by the formula (2-1), to obtain a compound represented by the formula (1-2) (R is a hydrogen atom).
The structure of the compound represented by the above formula (1-2) is obtained by 1 H-NMR、 13 C-NMR and FT-IR.
(production of the Compound represented by the formula (1-3))
The same procedure as in the above "(production of a compound represented by the formula (1-1)" was conducted except that 46.4 parts by weight of the compound represented by the formula (2-3) was used instead of 37.4 parts by weight of the compound represented by the formula (2-1), to obtain a compound represented by the formula (1-3) (R is a hydrogen atom).
The structure of the compound represented by the above formula (1-3) is obtained by 1 H-NMR、 13 C-NMR and FT-IR.
(production of the Compound represented by the formula (1-4))
The same procedure as in the above "(production of a compound represented by the formula (1-1)" was conducted except that 43.4 parts by weight of the compound represented by the formula (2-4) was used instead of 37.4 parts by weight of the compound represented by the formula (2-1), to obtain a compound represented by the formula (1-4) (R is a hydrogen atom).
The structure of the compound represented by the above formula (1-4) is obtained by 1 H-NMR、 13 C-NMR and FT-IR.
(production of the Compound represented by the formula (1-5))
The same procedure as in the above "(production of a compound represented by the formula (1-1)" was conducted except that 46.4 parts by weight of the compound represented by the formula (2-5) was used instead of 37.4 parts by weight of the compound represented by the formula (2-1), to obtain a compound represented by the formula (1-5) (R is a hydrogen atom).
The structure of the compound represented by the above formula (1-5) is obtained by 1 H-NMR、 13 C-NMR and FT-IR.
(production of the Compound represented by the formula (1-6))
The same procedure as in the above "(production of a compound represented by the formula (1-1)" was conducted except that 55.4 parts by weight of the compound represented by the formula (2-6) was used instead of 37.4 parts by weight of the compound represented by the formula (2-1), to obtain a compound represented by the formula (1-6) (R is a hydrogen atom).
The structure of the compound represented by the above formula (1-6) is obtained by 1 H-NMR、 13 C-NMR and FT-IR.
Examples 1 to 14 and comparative examples 1 to 9
The materials were stirred by a planetary stirring device (product of THINKY, "deaeration training Talang") in accordance with the mixing ratios shown in tables 1 and 2, and then uniformly mixed by a ceramic three-roll machine, to obtain the sealants for liquid crystal display elements of examples 1 to 14 and comparative examples 1 to 9.
< evaluation >
The sealants for liquid crystal display elements obtained in examples and comparative examples were evaluated as follows. The results are shown in tables 1 and 2.
(adhesiveness)
1 part by weight of spacer particles having an average particle diameter of 5 μm (Micropearl SP-2050, manufactured by water chemical industry Co., ltd.) was uniformly dispersed in 100 parts by weight of each of the sealants for liquid crystal display elements obtained in examples and comparative examples by using a planetary stirring device. Taking trace amount of dispersed spacing agentThe sealant of the particles was placed in the center of the glass substrate (20 mm. Times.50 mm. Times.0.7 mm in thickness) and the same type of glass substrate was superimposed thereon. The sealant for liquid crystal display element was developed, and 3000mJ/cm was irradiated with a metal halide lamp 2 After ultraviolet rays of (2) were heated at 120℃for 1 hour to cure the sealant, an adhesion test piece was obtained.
The adhesion strength of the obtained adhesion test piece was measured using a tensiometer. The bonding strength was set at 2.5kg/cm 2 The above cases were defined as "O", and the adhesive strength was less than 2.5kg/cm 2 The case of (2) was "X", and the adhesiveness was evaluated.
(moisture permeability prevention)
The sealants for liquid crystal display elements obtained in examples and comparative examples were applied to a smooth release film using a coater so that the thickness became 200 to 300. Mu.m. Next, 3000mJ/cm of irradiation was performed using a metal halide lamp 2 After ultraviolet rays of (2) were heated at 120℃for 1 hour to cure the sealant, a film for moisture permeability measurement was obtained. A cup for moisture permeability test was prepared by a method of moisture permeability test method (cup method) for moisture permeability packaging material according to JIS Z0208, and the obtained film for moisture permeability measurement was mounted and put into a constant temperature and humidity oven at 80℃and 90% RH to measure moisture permeability. The obtained moisture permeability is less than 60g/m 2 The 24hr case was set to "O", and 60g/m 2 24hr or more and less than 80g/m 2 The case of 24hr is referred to as "delta", and will be 80g/m 2 The moisture permeability was evaluated by setting "X" for 24hr or more.
(performance of preventing residue in a syringe)
The sealing agent 10g for liquid crystal display elements obtained in examples and comparative examples was sealed in a syringe (manufactured by Musashi Engineering Co., ltd., "PSY-10 EU-OR"), and a nozzle of 0.4 mm. Phi. Was attached. Then, the sealant was discharged at a pressure of 100 to 400kPa using a bench coater (manufactured by Musashi Engineering Co., ltd., "SHOTMASTER 300") and an air pulse type dispenser (manufactured by Musashi Engineering Co., ltd., "ML-808 EX"), and 9 frame-shaped seal patterns of 3.5 cm. Times.3.5 cm were drawn on a 15 cm. Times.15 cm glass substrate. Next, after 6 μl of liquid crystal was dropped into the frame of each seal pattern, the operation of bonding the substrates by vacuum pressure bonding was repeated to produce a cell. At this time, the production of the cell is completed at the time when the liquid crystal leakage occurs in all the cells, and the sealant remaining in the syringe is measured.
The performance of preventing the remaining of the sealant in the syringe was evaluated by setting "verygood" when the sealant remaining in the syringe was less than 3g, setting "good" when the sealant remaining in the syringe was 3g or more and less than 5g, setting "×" when the sealant remaining in the syringe was 5g or more.
TABLE 1
TABLE 2
Industrial applicability
According to the present invention, a sealant for a liquid crystal display element excellent in adhesion, moisture permeability resistance, and wall sticking prevention performance in a syringe can be provided. Further, according to the present invention, a liquid crystal display element using the sealant for a liquid crystal display element can be provided.
Claims (4)
1. A sealant for a liquid crystal display element, characterized by comprising a curable resin, a radical polymerization initiator and a thermosetting agent,
the curable resin comprises:
(A) A partially (meth) acrylic-modified epoxy compound having 3 or more aromatic rings in 1 molecule;
(B) At least 1 selected from bisphenol a type epoxy (meth) acrylate, bisphenol F type epoxy (meth) acrylate, bisphenol E type epoxy (meth) acrylate, a partially (meth) acrylic acid modified bisphenol a type epoxy compound, a partially (meth) acrylic acid modified bisphenol F type epoxy compound, and a partially (meth) acrylic acid modified bisphenol E type epoxy compound; and
(C) A (meth) acrylic compound having a molecular weight of 100 to 300.
2. The sealant for a liquid crystal display element according to claim 1, wherein the (meth) acrylic compound having a molecular weight of 100 or more and 300 or less is a monofunctional (meth) acrylic compound having only 1 (meth) acryloyl group in 1 molecule.
3. The sealant for a liquid crystal display element according to claim 1 or 2, wherein the content of the (meth) acrylic compound having a molecular weight of 100 to 300 in 100 parts by weight of the entire curable resin is 0.1 to 10 parts by weight.
4. A liquid crystal display element comprising the cured product of the sealant for a liquid crystal display element according to claim 1,2 or 3.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021103288 | 2021-06-22 | ||
| JP2021-103288 | 2021-06-22 | ||
| PCT/JP2022/024525 WO2022270462A1 (en) | 2021-06-22 | 2022-06-20 | Sealing agent for liquid crystal display elements, and liquid crystal display element |
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| Publication Number | Publication Date |
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| CN117203577A true CN117203577A (en) | 2023-12-08 |
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| CN202280030400.XA Pending CN117203577A (en) | 2021-06-22 | 2022-06-20 | Sealing agent for liquid crystal display element and liquid crystal display element |
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| Country | Link |
|---|---|
| JP (1) | JP7253118B1 (en) |
| KR (1) | KR20240023110A (en) |
| CN (1) | CN117203577A (en) |
| TW (1) | TW202313713A (en) |
| WO (1) | WO2022270462A1 (en) |
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| WO2023176843A1 (en) * | 2022-03-18 | 2023-09-21 | 積水化学工業株式会社 | Liquid crystal display element sealant and liquid crystal display element |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH0714694B2 (en) | 1988-09-29 | 1995-02-22 | 三菱自動車工業株式会社 | Wrinkle-proofing method for vinyl chloride trim skin |
| JP3583326B2 (en) | 1999-11-01 | 2004-11-04 | 協立化学産業株式会社 | Sealant for dripping method of LCD panel |
| CN104718231B (en) * | 2012-10-12 | 2017-03-29 | 协立化学产业株式会社 | The manufacture method of glycidyl ether based compound, liquid crystal sealing agent and glycidyl ether based compound |
| JP6754933B2 (en) * | 2014-04-09 | 2020-09-16 | 協立化学産業株式会社 | Liquid crystal sealant applicable to flexible liquid crystal panels |
| CN113811559B (en) * | 2019-05-14 | 2024-05-31 | 协立化学产业株式会社 | Sealant for liquid crystal instilling method |
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2022
- 2022-06-20 JP JP2022540914A patent/JP7253118B1/en active Active
- 2022-06-20 WO PCT/JP2022/024525 patent/WO2022270462A1/en active Application Filing
- 2022-06-20 CN CN202280030400.XA patent/CN117203577A/en active Pending
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| KR20240023110A (en) | 2024-02-20 |
| WO2022270462A1 (en) | 2022-12-29 |
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