CN110226120A - Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element - Google Patents
Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element Download PDFInfo
- Publication number
- CN110226120A CN110226120A CN201880007538.1A CN201880007538A CN110226120A CN 110226120 A CN110226120 A CN 110226120A CN 201880007538 A CN201880007538 A CN 201880007538A CN 110226120 A CN110226120 A CN 110226120A
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- Prior art keywords
- liquid crystal
- methyl
- mentioned
- crystal display
- compound
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 92
- 239000003566 sealing material Substances 0.000 title claims abstract description 53
- 239000004020 conductor Substances 0.000 title claims abstract description 9
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- 229920005989 resin Polymers 0.000 claims abstract description 22
- 239000011347 resin Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 81
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- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 58
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 49
- 238000000034 method Methods 0.000 description 31
- 239000000126 substance Substances 0.000 description 27
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000758 substrate Substances 0.000 description 20
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- QSBINWBNXWAVAK-PSXMRANNSA-N PE-NMe(16:0/16:0) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCNC)OC(=O)CCCCCCCCCCCCCCC QSBINWBNXWAVAK-PSXMRANNSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 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
- FYYIUODUDSPAJQ-XVBQNVSMSA-N [(1S,6R)-7-oxabicyclo[4.1.0]heptan-3-yl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CC[C@H]2O[C@H]2C1 FYYIUODUDSPAJQ-XVBQNVSMSA-N 0.000 description 1
- IOQQEGTZQHWGNN-UHFFFAOYSA-M [NH4+].[Br-].CC1=C(C(=[N+](C=C1)CCCCCCCCCCCCCCCC)C)C.[Br-] Chemical compound [NH4+].[Br-].CC1=C(C(=[N+](C=C1)CCCCCCCCCCCCCCCC)C)C.[Br-] IOQQEGTZQHWGNN-UHFFFAOYSA-M 0.000 description 1
- LRCPOJGBEQAERD-UHFFFAOYSA-M [P].[Br-].C(CCC)[P+](CCCC)(CCCC)CCCC Chemical compound [P].[Br-].C(CCC)[P+](CCCC)(CCCC)CCCC LRCPOJGBEQAERD-UHFFFAOYSA-M 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical class 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
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 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
- KPTLPIAOSCGETM-UHFFFAOYSA-N benzene 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O.c1ccccc1 KPTLPIAOSCGETM-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 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 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229920001427 mPEG Polymers 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
- 238000005259 measurement Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010409 thin film 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
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000007666 vacuum forming Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- 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
Abstract
Sealing material for liquid crystal display device that is excellent the object of the present invention is to provide the curability of the light for long wavelength and being able to suppress foreign matter generation.It is further an object that providing using the sealing material for liquid crystal display device and manufactured conductive material and liquid crystal display element up and down.The present invention is a kind of sealing material for liquid crystal display device, and containing curable resin, Photoepolymerizationinitiater initiater and maleimide compound, absorptivity of the above-mentioned Photoepolymerizationinitiater initiater at wavelength 430nm is 0.8 × 102ML/gcm or more.
Description
Technical field
Liquid crystal display element that is excellent the present invention relates to the curability of the light for long wavelength and being able to suppress foreign matter generation
Use sealant.In addition, the present invention relates to use the sealing material for liquid crystal display device and manufactured conductive material and liquid crystal up and down
Display element.
Background technique
In recent years, the manufacturing method as liquid crystal display elements such as liquid crystal displays, from shortening productive temp time, liquid
From the perspective of brilliant dosage optimizes, photo-thermal is used as using patent document 1, patent document 2 open and with admittedly
The liquid crystal drop under type for being referred to as technique of dripping of change type sealant.
In technique of dripping, frame-shaped is formed on one distributed in two electroded transparent substrates firstly, passing through
Seal pattern.Then, the tiny droplets of liquid crystal are dripped into whole face in the frame of transparent substrate in the state that sealant is uncured, stood
It is bonded another transparent substrate, and the light such as ultraviolet light are irradiated to sealing to carry out precuring.Thereafter, liquid crystal anneal when into
Row heats to carry out main solidification, makes liquid crystal display element.It, can be with high if carrying out the fitting of substrate under reduced pressure
Efficiency system liquid making crystal display element, now, the technique of dripping become the mainstream of the manufacturing method of liquid crystal display element.
However, in the modern times that the various mobile devices for being attached to liquid crystal display panels such as mobile phone, portable game become increasingly popular,
The miniaturization of equipment is most highly desirable project.As the method for device miniaturization, the narrow architrave of liquid crystal display part can be enumerated
Change, such as the position of sealing is configured the operation (being also referred to as narrow architrave design below) under black matrix.
However, for the design of narrow architrave, since sealant is configured in the underface of black matrix, if carried out
It drips technique, then the light for irradiating sealant when carrying out photocuring is blocked, and light will not reach the inside of sealant and exist
The problem of solidification becomes inadequate.Like this, if the solidification of sealant becomes inadequate, uncured sealant ingredient is molten
Out into liquid crystal, because the curing reaction caused by the sealant ingredient that is dissolved out promotes in liquid crystal, thus there is that liquid crystal occurs is dirty
The problem of dye.
In addition, having carried out ultraviolet irradiation usually as making sealant that the method for photocuring occur, but in liquid crystal drop
In lower technique, due to making sealant cures after the liquid crystal that drips, thus there are problems that deteriorating liquid crystal because irradiating ultraviolet light.
Liquid crystal is caused to deteriorate because of ultraviolet light in order to prevent, it may be considered that cooperate the photopolymerization excellent for the reactivity of the light of long wavelength
Initiator makes its photocuring using the light via long wavelength obtained by cut-off filter etc..However, having used this photopolymerization
In the case where initiator, be partially cured in a small amount of light of the cause of photocuring process there are sealant and generate foreign matter etc.
Problem.
Existing technical literature
Patent document
Patent document 1: Japanese Unexamined Patent Publication 2001-133794 bulletin
Patent document 2: International Publication No. 02/092718
Summary of the invention
Problems to be solved by the invention
Liquid that is excellent the object of the present invention is to provide the curability of the light for long wavelength and being able to suppress foreign matter generation
Crystal display element sealant.It is further an object that providing using the sealing material for liquid crystal display device and being made
Conductive material up and down and liquid crystal display element.
Means for solving the problems
The present invention is a kind of sealing material for liquid crystal display device, contains curable resin, Photoepolymerizationinitiater initiater and Malaysia
Imide compound, absorptivity of the above-mentioned Photoepolymerizationinitiater initiater at wavelength 430nm are 0.8 × 102ML/gcm or more.
Hereinafter, the present invention is described in detail.
The inventors of the present invention surprisingly it has been found that: by cooperating maleimide compound into sealant, so as to obtain
It can inhibit by sealant the excellent Photoepolymerizationinitiater initiater of the reactivity using the light for long wavelength in photocuring process
The sealing material for liquid crystal display device of the generation of foreign matter be partially cured before caused by, so as to complete the present invention.
Sealing material for liquid crystal display device of the invention contains Photoepolymerizationinitiater initiater.
Absorptivity of the above-mentioned Photoepolymerizationinitiater initiater at wavelength 430nm is 0.8 × 102ML/gcm or more.Hereinafter,
It is 0.8 × 10 by the absorptivity at wavelength 430nm2The Photoepolymerizationinitiater initiater of mL/gcm or more is known as " of the present invention
Photoepolymerizationinitiater initiater ".
By making absorptivity 0.8 × 10 of the Photoepolymerizationinitiater initiater of the present invention at wavelength 430nm2mL/g·
Cm or more, so that sealing material for liquid crystal display device of the invention becomes excellent for the curability of the light of long wavelength.This
The preferred lower limit of absorptivity of the invention Photoepolymerizationinitiater initiater at wavelength 430nm is 1.0 × 102mL/g·cm。
In addition, the preferred upper limit of absorptivity of the Photoepolymerizationinitiater initiater of the present invention at wavelength 430nm be 1.0 ×
104mL/g·cm。
It should be noted that above-mentioned absorptivity can measure as follows: will make in such a way that concentration reaches 0.1mg/mL
For measure object compound be dissolved in solvent after, be measured using spectrophotometer.
As long as above-mentioned solvent can dissolve the compound as measure object and under the absorbing wavelength to be measured
There is no the solvent of extinction, there is no particular limitation, can enumerate such as acetonitrile, methanol.
Photoepolymerizationinitiater initiater of the present invention from the excellent aspect of reactivity of the light for long wavelength and it is preferred that
Chemical combination for the compound with structure shown in following formula (1), with structure shown in 1 formula (1) in more preferably 1 molecule
Object, further preferably following formula (2-1) compound represented and/or following formula (2-2) compound represented.
[changing 1]
In formula (1), * is bonding position.
[changing 2]
In formula (2-1), (2-2), R is the structure from monofunctional epoxy compound.In formula (2-1), m be 1~5 it is whole
Number.
As the method for manufacturing compound shown in above-mentioned (2-1), can enumerate for example will in the presence of basic catalyst
Thio xanthene -9- the ketone of 2- (Carboxvmethoxv) -9H- and monofunctional epoxy compound are in 80 DEG C or more and 130 DEG C of conditions below
The lower method etc. for reacting it while stirring 6~72 hours.
In addition, the presence for example in basic catalyst can be enumerated as the method for manufacturing compound shown in above-mentioned (2-2)
It is lower by the thio xanthene -9- ketone of 2- hydroxyl -9H- and monofunctional epoxy compound one under the conditions of 80 DEG C or more and 130 DEG C below
Stir the method etc. for reacting it in side.
Hereinafter, it is directed to the thio xanthene -9- ketone of 2- (Carboxvmethoxv) -9H- and the thio xanthene -9- ketone of 2- hydroxyl -9H-,
Referred to as " raw material thioxanthone derivates ".
Above-mentioned monofunctional epoxy compound preferably includes the aromatic series of the substituent group with above 1 or more the carbon number of at least one
The aliphatic ring of ring or the substituent group with above 1 or more the carbon number of at least one.
As above-mentioned aromatic ring or above-mentioned aliphatic ring, such as phenyl ring, naphthalene nucleus, anthracene nucleus, cyclobutane ring, ring can be enumerated
At least one in the aromatic rings such as pentane ring, cyclohexane ring, cyclooctane ring, norbornene ring, tristane ring or aliphatic ring
Group obtained from the above hydrogen atom is replaced by the substituent group of 1 or more carbon number.
The substituent group of above-mentioned 1 or more carbon number can be straight-chain, or branched.In taking for above-mentioned 1 or more carbon number
In the case where Dai Jiwei straight-chain, preferably 6 or more carbon number, 10 or more more preferable carbon number.It is in the substituent group of above-mentioned 1 or more carbon number
In the case where branched, preferred 4 or more carbon number.In addition, 1 or more carbon number possessed by above-mentioned aromatic ring or above-mentioned aliphatic ring
The carbon number of substituent group be preferably that the molecular weight of above-mentioned monofunctional epoxy compound reaches aftermentioned 300 numbers below.
As the substituent group of 1 or more carbon number possessed by above-mentioned aromatic ring or above-mentioned aliphatic ring, preferably alkyl.
As above-mentioned monofunctional epoxy compound, such as alkyl phenyl glycidyl ether can be enumerated, there is glycidol
Toluene fulfonate, 2- epoxy group -4- vinyl cyclohexane, methacrylic acid -3,4- epoxycyclohexanecarboxylate of base etc..
As abovementioned alkyl phenyl glycidyl ether, such as o-methyl-phenyl glycidol ether, methylbenzene can be enumerated
Base glycidol ether, p-methylphenyl glycidol ether, to tert-butyl-phenyl glycidol ether etc..
As the commercially available product among above-mentioned monofunctional epoxy compound, such as Nagase ChemteX corporation can be enumerated
Monofunctional epoxy compound, the monofunctional epoxy compound of ADEKA corporation, Mitsubishi Chemical Ind monofunctional epoxy
Close object, the monofunctional epoxy compound of Tokyo chemical conversion industry corporation, monofunctional epoxy compound of Daicel corporation etc..
As the monofunctional epoxy compound of above-mentioned Nagase ChemteX corporation, such as Denacol can be enumerated
EX-146 etc..
As the monofunctional epoxy compound of above-mentioned ADEKA corporation, such as ED-509S, ED-509E, ED- can be enumerated
529 etc..
As the monofunctional epoxy compound of above-mentioned Mitsubishi Chemical Ind, can enumerate such as YED-122.
As the monofunctional epoxy compound of above-mentioned Tokyo chemical conversion industry corporation, such as glycidyl 2- can be enumerated
Methoxyphenyl ether, 1- methyl-1,2- 7-oxa-bicyclo[4.1.0 etc..
As the monofunctional epoxy compound of above-mentioned Daicel corporation, can enumerate such as CELLOXIDE 2000,
CYCLOMER M100 etc..
From the viewpoint of the compatibility of Photoepolymerizationinitiater initiater of the present invention and curable resin, above-mentioned simple function ring
The molecular weight of oxygen compound is preferably 300 or less.
As use ratio when reacting above-mentioned raw materials thioxanthone derivates with above-mentioned monofunctional epoxy compound,
With molar ratio computing, preferably raw material thioxanthone derivates: monofunctional epoxy compound=1: 1~10: 1.By making above-mentioned raw materials
The use ratio of thioxanthone derivates and above-mentioned monofunctional epoxy compound is the range, so as to manufacture in high yield
State formula (2-1) compound represented or above-mentioned formula (2-2) compound represented.
As the alkalinity used when reacting above-mentioned raw materials thioxanthone derivates with above-mentioned monofunctional epoxy compound
Catalyst, preferably the organic phosphoric acid compound and/or amine compounds of trivalent.
As above-mentioned basic catalyst, specifically, such as triphenylphosphine, triethylamine, tripropyl amine (TPA), tetramethyl can be enumerated
Ethylenediamine, dimethyllaurylamine, triethyl benzyl ammonia chloride, trimethyl cetylpyridinium bromide ammonium, tetrabutylammonium bromide, trimethyl fourth
Base phosphonium bromide, tetrabutyl phosphonium bromide phosphorus etc..Wherein, preferably triphenylphosphine.
Come in the form of Polymer Supported basic catalyst in addition, above-mentioned basic catalyst can also be supported in polymer
It uses.
Among Photoepolymerizationinitiater initiater of the present invention, as in addition to the above-mentioned compound with structure shown in formula (1) it
Outer Photoepolymerizationinitiater initiater can enumerate for example bis- (2,4,6- trimethylbenzoyl) phenyl phosphine oxides etc..
Relative to total 100 parts by weight of curable resin and maleimide compound, photopolymerization of the present invention
The preferred lower limit of the content of initiator is 0.1 parts by weight, preferred upper limit is 20 parts by weight.By making photopolymerization of the present invention
The content of initiator is 0.1 parts by weight or more, so that the light of gained sealing material for liquid crystal display device for long wavelength
Curability becomes more excellent.By make Photoepolymerizationinitiater initiater of the present invention 20 parts by weight of content hereinafter, so that
The effect for inhibiting gained sealing material for liquid crystal display device to generate foreign matter becomes more excellent.Photoepolymerizationinitiater initiater of the present invention
Content more preferable lower limit be 0.2 parts by weight, further preferred lower limit is 0.3 parts by weight, still more preferably lower limit is 0.5
Parts by weight, particularly preferred lower limit are 1 parts by weight.The more preferable upper limit of the content of Photoepolymerizationinitiater initiater of the present invention is 10 weights
Measure part, the further preferred upper limit is 5 parts by weight.
Sealing material for liquid crystal display device of the invention can contain thermal polymerization within the scope without prejudice to the object of the present invention
Initiator.
As above-mentioned thermal polymerization, can enumerate such as comprising hot polymerization azo-compound, organic peroxide
Close initiator.It wherein, preferably include the polymeric azo initiator of polymeric azo compound.
It should be noted that above-mentioned " polymeric azo compound " refers in this specification: with azo group and Yin Re
Generation can make the cured free radical of (methyl) acryloxy, 300 or more number-average molecular weight compound.
The preferred lower limit of the number-average molecular weight of above-mentioned polymeric azo compound is 1000, preferred upper limit is 300,000.Pass through
Make the number-average molecular weight of the above-mentioned polymeric azo compound range, so as to inhibit liquid crystal pollution and easy and curability
Resin mixing.The more preferable lower limit of the number-average molecular weight of above-mentioned polymeric azo compound is 5000, the more preferable upper limit is 100,000,
Further preferred lower limit is 10,000, the further preferred upper limit is 90,000.
It should be noted that above-mentioned number-average molecular weight is to use tetrahydro in gel permeation chromatography (GPC) in this specification
Furans is measured as solvent, and the value found out using polystyrene conversion.It measures as by GPC based on polyphenyl
The pillar when number-average molecular weight of ethylene conversion, can enumerate such as Shodex LF-804 (Showa electrician corporation).
As above-mentioned polymeric azo compound, can enumerate for example with being bonded multiple polycyclic oxygen by azo group
The compound of structure obtained by the units such as alkane, dimethyl silicone polymer.
As the above-mentioned polymeric azo for having and being bonded structure obtained by the units such as multiple polyalkylene oxides by azo group
Compound, preferably with the compound of polyethylene oxide structure.
As above-mentioned polymeric azo compound, specifically, such as 4 can be enumerated, 4 '-azos are bis- (4- cyanopentanoic acid)
With condensation polymer, 4, the 4 '-azos bis- (4- cyanopentanoic acids) of polyalkylene glycol and with the dimethyl silicone polymer of terminal amino group
Condensation polymer etc..
As the commercially available product among above-mentioned polymeric azo compound, can enumerate such as VPE-0201, VPE-0401,
VPE-0601, VPS-0501, VPS-1001 (being Fujiphoto and the pure medicine corporation of light) etc..
In addition, the azo-compound as on-macromolecular, can enumerate such as V-65, V-501 (is Fujiphoto and light
Pure medicine corporation) etc..
As above-mentioned organic peroxide, such as ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl group can be enumerated
Peroxide, peroxyester, diacyl peroxide, peroxy dicarbonate etc..
Relative to total 100 parts by weight of curable resin and maleimide compound, above-mentioned thermal polymerization
The preferred lower limit of content is 0.05 parts by weight, preferred upper limit is 10 parts by weight.By the content for making above-mentioned thermal polymerization
More than 0.05 parts by weight, the Thermocurable of sealing material for liquid crystal display device of the invention becomes more excellent.By making above-mentioned heat
The content of polymerization initiator is for 10 parts by weight hereinafter, low liquid crystal pollution, the guarantor of sealing material for liquid crystal display device of the invention
Depositing stability becomes more excellent.The more preferable lower limit of the content of above-mentioned thermal polymerization is 0.1 parts by weight, the more preferable upper limit is
5 parts by weight.
Sealing material for liquid crystal display device of the invention contains curable resin.
As described later, in the present invention, maleimide compound is not included in above-mentioned curable resin.
Above-mentioned curable resin preferably comprises (methyl) acrylic compounds.
As above-mentioned (methyl) acrylic compounds, such as (methyl) acrylate compounds, epoxy (first can be enumerated
Base) acrylate, carbamate (methyl) acrylate etc..Wherein, preferably epoxy (methyl) acrylate.In addition, from
Reactive height is set out, and above-mentioned (methyl) acrylic compounds are preferably in the molecule with 2 or more (methyl) propylene
Acyl group.
It should be noted that above-mentioned " (methyl) acrylic compounds " refer to acrylic compounds or methacrylic acid in this specification
Class, above-mentioned " (methyl) acrylic compounds " refer to the compound with (methyl) acryloyl group, above-mentioned " (methyl) acryloyl
Base " refers to acryloyl group or methylacryloyl.In addition, above-mentioned " (methyl) acrylate " refers to acrylate or metering system
Acid esters.In turn, above-mentioned " epoxy (methyl) acrylate " indicates to make all epoxy groups and (methyl) propylene in epoxide
Compound obtained from acid is reacted.
As the monofunctional compound among above-mentioned (methyl) acrylate compounds, such as (methyl) propylene can be enumerated
Sour methyl esters, (methyl) ethyl acrylate, (methyl) propyl acrylate, (methyl) n-butyl acrylate, (methyl) i-butyl
Ester, (methyl) tert-butyl acrylate, (methyl) 2-EHA, (methyl) n-octyl, (methyl) acrylic acid
Different monooctyl ester, the different nonyl ester of (methyl) acrylic acid, (methyl) isodecyl acrylate, (methyl) lauryl acrylate, (methyl) acrylic acid
Different myristin, (methyl) stearyl acrylate, (methyl) acrylic acid 2- hydroxy methacrylate, (methyl) acrylic acid 2- hydroxy propyl ester,
(methyl) acrylic acid 2- hydroxybutyl, (methyl) acrylic acid 4- hydroxybutyl, (methyl) cyclohexyl acrylate, (methyl) acrylic acid
Isobornyl thiocyanoacetate, (methyl) acrylic acid dicyclopentenyloxyethyl methacrylate, (methyl) benzyl acrylate, (methyl) acrylic acid 2- methoxy acrylate, (first
Base) acrylic acid 2- ethoxy ethyl ester, (methyl) acrylic acid 2- butoxyethyl, (methyl) acrylic acid 2- phenoxy ethyl, methoxy
Ethyl glycol (methyl) acrylate, methoxy poly (ethylene glycol) (methyl) acrylate, phenoxy group diethylene glycol (methyl) propylene
Acid esters, phenoxy group polyethylene glycol (methyl) acrylate, (methyl) tetrahydrofurfuryl acrylate, ethyl carbitol (methyl) acrylic acid
Ester, (methyl) acrylic acid 2,2,2- trifluoro ethyl ester, 2,2,3,3- tetrafluoro propyl ester of (methyl) acrylic acid, (methyl) acrylic acid 1H, 1H,
5H- octafluoro pentyl ester, acid imide (methyl) acrylate, (methyl) dimethylaminoethyl acrylate, (methyl) acrylic acid diethylamino
Base ethyl ester, 2- (methyl) acryloyl-oxyethyl succinic acid, 2- (methyl) acryloyl-oxyethyl hexahydrophthalic acid, 2-
(methyl) acryloyl-oxyethyl 2- hydroxypropyl phthalate, 2- (methyl) acryloyl-oxyethyl phosphate, (first
Base) glycidyl acrylate etc..
In addition, closing object as the difunctional among above-mentioned (methyl) acrylate compounds, such as 1,3- can be enumerated
Butanediol two (methyl) acrylate, 1,4-butanediol two (methyl) acrylate, 1,6- hexylene glycol two (methyl) acrylate,
1,9- nonanediol two (methyl) acrylate, 1,10- decanediol two (methyl) acrylate, ethylene glycol two (methyl) acrylic acid
Ester, diethylene glycol two (methyl) acrylate, tetraethylene glycol two (methyl) acrylate, polyethylene glycol two (methyl) acrylic acid
Ester, 2- normal-butyl -2- ethyl -1,3-PD two (methyl) acrylate, dipropylene glycol two (methyl) acrylate, 3 the third two
Alcohol two (methyl) acrylate, polypropylene glycol (methyl) acrylate, neopentyl glycol two (methyl) acrylate, ethylene oxide add
At bisphenol-A two (methyl) acrylate, propylene oxide addition bisphenol-A two (methyl) acrylate, ethyleneoxide addition Bisphenol F two
(methyl) acrylate, dihydroxymethyl dicyclopentadienyl two (methyl) acrylate, two (first of ethylene-oxide-modified isocyanuric acid
Base) acrylate, 2- hydroxyl -3- (methyl) acryloxypropyl (methyl) acrylate, carbonate diol two (methyl) third
Olefin(e) acid ester, polyetherdiol two (methyl) acrylate, polyester-diol two (methyl) acrylate, polycaprolactone glycol two (methyl)
Acrylate, polybutadiene diol two (methyl) acrylate etc..
In addition, example can be enumerated as the compound more than trifunctional among above-mentioned (methyl) acrylate compounds
Such as trimethylolpropane tris (methyl) acrylate, ethyleneoxide addition trimethylolpropane tris (methyl) acrylate, epoxy
Propane addition trimethylolpropane tris (methyl) acrylate, caprolactone modification trimethylolpropane tris (methyl) acrylate,
Ethyleneoxide addition isocyanuric acid three (methyl) acrylate, glycerol three (methyl) acrylate, propylene oxide addition glycerol three
(methyl) acrylate, pentaerythrite three (methyl) acrylate, three (methyl) acryloyl-oxyethyl phosphates, bis- (three hydroxyls
Methylpropane) four (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylic acid
Ester, dipentaerythritol six (methyl) acrylate etc..
As above-mentioned epoxy (methyl) acrylate, can enumerate for example by conventionally make epoxide with
Epoxy obtained from (methyl) acrylic acid is reacted in the presence of basic catalyst (methyl) acrylate etc..
As the epoxide become for synthesizing the raw material of above-mentioned epoxy (methyl) acrylate, can enumerate for example
Bisphenol A type epoxy compound, bisphenol F type epoxy compound, bisphenol S type epoxy compound, 2,2 '-diallyl bisphenol type rings
Oxygen compound, A Hydrogenated Bisphenol A type ring oxygen compound, propylene oxide addition bisphenol A type epoxy compound, the oxidation of resorcinol type ring
Close object, biphenyl type epoxy compound, thioether-type epoxide, diphenyl ether type epoxide, dicyclopentadiene type epoxy
Close object, naphthalene type ring oxygen compound, phenol novolak type epoxide, o-cresol novolak type epoxy compound, bicyclopentadiene phenol
Aldehyde type ring oxygen compound, biphenyl novolak type epoxy compound, naphthol novolac type ring oxygen compound, glycidyl amine epoxy chemical combination
Object, alkyl polyols type ring oxygen compound, modified rubber type ring oxygen compound, epihydric alcohol ester compound etc..
As the commercially available product among above-mentioned bisphenol A type epoxy compound, such as jER828EL, jER1004 can be enumerated (
For Mitsubishi Chemical Ind's system), EPICLON 850CRP (DIC corporation) etc..
As the commercially available product among above-mentioned bisphenol F type epoxy compound, can enumerate such as jER806, jER4004 (is
Mitsubishi Chemical Ind's system) etc..
As the commercially available product among above-mentioned bisphenol S type epoxy compound, such as EPICLON EXA1514 (DIC can be enumerated
Corporation) etc..
As the commercially available product among above-mentioned 2,2 '-diallyl bisphenol type ring oxygen compounds, such as RE- can be enumerated
810NM (Japanese chemical drug corporation) etc..
As the commercially available product among above-mentioned A Hydrogenated Bisphenol A type ring oxygen compound, such as EPICLON EXA7015 can be enumerated
(DIC corporation) etc..
As the commercially available product among above-mentioned propylene oxide addition bisphenol A type epoxy compound, such as EP- can be enumerated
4000S (ADEKA corporation) etc..
As the commercially available product among above-mentioned resorcinol type ring oxygen compound, such as EX-201 (Nagase can be enumerated
ChemteX corporation) etc..
As the commercially available product among above-mentioned biphenyl type epoxy compound, such as jER YX-4000H (Mitsubishi can be enumerated
Learn corporation) etc..
As the commercially available product among above-mentioned thioether-type epoxide, can enumerating such as YSLV-50TE, (gold is lived by Nippon Steel
Chemical company's system) etc..
As the commercially available product among above-mentioned diphenyl ether type epoxide, can enumerating such as YSLV-80DE, (Nippon Steel is lived
Aurification corporation) etc..
As the commercially available product among above-mentioned dicyclopentadiene type epoxy compound, such as EP-4088S (ADEKA can be enumerated
Corporation) etc..
As the commercially available product among above-mentioned naphthalene type ring oxygen compound, such as EPICLON HP4032, EPICLON can be enumerated
EXA-4700 (being DIC corporation) etc..
As the commercially available product among above-mentioned phenol novolak type epoxide, such as EPICLON N-770 can be enumerated
(DIC corporation) etc..
As the commercially available product among above-mentioned o-cresol novolak type epoxy compound, such as EPICLON N-670- can be enumerated
EXP-S (DIC corporation) etc..
As the commercially available product among above-mentioned dicyclopentadiene phenolic type ring oxygen compound, such as EPICLON can be enumerated
HP7200 (DIC corporation) etc..
As the commercially available product among above-mentioned biphenyl novolak type epoxy compound, such as NC-3000P (Japanization can be enumerated
Medicine corporation) etc..
As the commercially available product among above-mentioned naphthol novolac type ring oxygen compound, such as ESN-165S (Nippon Steel can be enumerated
Firmly aurification corporation) etc..
As the commercially available product among above-mentioned glycidyl amine epoxy compound, such as jER630 (Mitsubishi can be enumerated
Learn corporation), EPICLON 430 (DIC corporation), TETRAD-X (gas chemical company, Mitsubishi system) etc..
As the commercially available product among abovementioned alkyl polyol type epoxide, such as ZX-1542 (Nippon Steel can be enumerated
Firmly aurification corporation), EPICLON 726 (DIC corporation), EPOLIGHT 80MFA (chemical company, common prosperity society system),
Denacol EX-611 (Nagase ChemteX corporation) etc..
Commercially available product among modified version epoxide as above-mentioned rubber can enumerate such as YR-450, YR-207 (
Live aurification corporation for Nippon Steel), Epolead PB (Daicel corporation) etc..
As the commercially available product among above-mentioned epihydric alcohol ester compound, such as Denacol EX-147 can be enumerated
(Nagase ChemteX corporation) etc..
As other commercially available products among above-mentioned epoxide, can enumerate such as YDC-1312, YSLV-80XY,
YSLV-90CR (being that aurification corporation is lived by Nippon Steel), XAC4151 (Asahi Kasei Corporation's system), jER1031, jER1032 are (
For Mitsubishi Chemical Ind's system), EXA-7120 (DIC corporation), TEPIC (Nissan Chemical corporation) etc..
As the commercially available product among above-mentioned epoxy (methyl) acrylate, such as DAICEL-ALLNEX company can be enumerated
Epoxy (methyl) acrylate of system, epoxy (methyl) acrylate of chemical industrial company, the village Xin Zhong, common prosperity society chemistry are public
Take charge of epoxy (methyl) acrylate, epoxy (methyl) acrylate of Nagase ChemteX corporation etc. of system.
As epoxy (methyl) acrylate of above-mentioned DAICEL-ALLNEX corporation, can enumerate for example
EBECRYL860、EBECRYL3200、EBECRYL3201、EBECRYL3412、EBECRYL3600、EBECRYL3700、
EBECRYL3701、EBECRYL3702、EBECRYL3703、EBECRYL3800、EBECRYL6040、EBECRYL RDX63182
Deng.
As epoxy (methyl) acrylate of chemical industrial company, the above-mentioned village Xin Zhong, can enumerate such as EA-1010,
EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 etc..
As epoxy (methyl) acrylate of chemical company, above-mentioned common prosperity society, such as Epoxy Ester can be enumerated
M-600A、Epoxy Ester 40EM、Epoxy Ester 70PA、Epoxy Ester 200PA、Epoxy Ester 80MFA、
Epoxy Ester 3002M、Epoxy Ester 3002A、Epoxy Ester 1600A、Epoxy Ester 3000M、Epoxy
Ester 3000A, Epoxy Ester 200EA, Epoxy Ester 400EA etc..
As epoxy (methyl) acrylate of above-mentioned Nagase ChemteX corporation, such as Denacol can be enumerated
Acrylate DA-141, Denacol Acrylate DA-314, Denacol Acrylate DA-911 etc..
Above-mentioned carbamate (methyl) acrylate can be for example, by (methyl) acrylic acid derivative 2 for making to have hydroxyl
Equivalent in the presence of the tin based compound of catalytic amount with 2 isocyanate group 1 equivalent of isocyanate compound into
Row reaction is to obtain.
As above-mentioned isocyanate compound, such as isophorone diisocyanate, 2,4- toluene diisocyanate can be enumerated
Acid esters, 2,6- toluene di-isocyanate(TDI), hexamethylene diisocyanate, trimethyl hexamethylene diisocyanate, diphenylmethyl
4,4 '-diisocyanate (MDI) of alkane-, hydrogenation MDI, polymeric MDI, 1,5- naphthalene diisocyanate, norbornene alkyl diisocyanate,
Tolidine diisocyanate, benzene dimethylene diisocyanate (XDI), hydrogenation XDI, lysine diisocyanate, triphenyl
Methane triisocyanate, three (isocyanate phenyl) thiophosphates, tetramethylxylylene diisocyanate, 1,6,11-
Hendecane triisocyanate etc..
In addition, also can be used as above-mentioned isocyanate compound through polyalcohol and excessive isocyanates chemical combination
The isocyanate compound of chain elongation obtained from the reaction of object.
As above-mentioned polyalcohol, can enumerate for example ethylene glycol, propylene glycol, glycerol, D-sorbite, trimethylolpropane,
Carbonate diol, polyetherdiol, polyester-diol, polycaprolactone glycol etc..
As above-mentioned (methyl) acrylic acid derivative with hydroxyl, for example single (methyl) dihydroxypropyl alkane can be enumerated
Base ester, list (methyl) acrylate of dihydric alcohol, trihydroxylic alcohol list (methyl) acrylate or two (methyl) acrylate, epoxy
(methyl) acrylate etc..
As above-mentioned list (methyl) hydroxyalkyl acrylates, can enumerate such as (methyl) acrylic acid 2- hydroxy methacrylate,
(methyl) acrylic acid 2- hydroxy propyl ester, (methyl) acrylic acid 2- hydroxybutyl, (methyl) acrylic acid 4- hydroxybutyl etc..
As above-mentioned dihydric alcohol, such as ethylene glycol, propylene glycol, 1,3-PD, 1,3-BDO, Isosorbide-5-Nitrae-fourth can be enumerated
Glycol, polyethylene glycol etc..
As above-mentioned trihydroxylic alcohol, can enumerate such as trimethylolethane, trimethylolpropane, glycerol.
As above-mentioned epoxy (methyl) acrylate, can enumerate such as bisphenol-a epoxy acrylate.
As the commercially available product among above-mentioned carbamate (methyl) acrylate, such as East Asia Synesis Company can be enumerated
Carbamate (methyl) acrylate, root of carbamate (methyl) acrylate of system, DAICEL-ALLNEX corporation
Carbamate (methyl) acrylate of upper industrial group, chemical industrial company, the village Xin Zhong carbamate (methyl)
Acrylate, carbamate (methyl) acrylate of chemical company, common prosperity society etc..
As carbamate (methyl) acrylate of above-mentioned East Asia Synesis Company, can enumerate such as M-1100,
M-1200, M-1210, M-1600 etc..
As carbamate (methyl) acrylate of above-mentioned DAICEL-ALLNEX corporation, can enumerate for example
EBECRYL210、EBECRYL220、EBECRYL230、EBECRYL270、EBECRYL1290、EBECRYL2220、
EBECRYL4827、EBECRYL4842、EBECRYL4858、EBECRYL5129、EBECRYL6700、EBECRYL8402、
EBECRYL8803, EBECRYL8804, EBECRYL8807, EBECRYL9260 etc..
As carbamate (methyl) acrylate of above-mentioned Gen Shang industrial group, such as Art can be enumerated
Resin UN-330、Art Resin SH-500B、Art Resin UN-1200TPK、Art Resin UN-1255、Art
Resin UN-3320HB, Art Resin UN-7100, Art Resin UN-9000A, Art Resin UN-9000H etc..
As carbamate (methyl) acrylate of chemical industrial company, the above-mentioned village Xin Zhong, such as U- can be enumerated
2HA、U-2PHA、U-3HA、U-4HA、U-6H、U-6HA、U-6LPA、U-10H、U-15HA、U-108、U-108A、U-122A、U-
122P、U-324A、U-340A、U-340P、U-1084A、U-2061BA、UA-340P、UA-4000、UA-4100、UA-4200、
UA-4400, UA-5201P, UA-7100, UA-7200, UA-W2A etc..
As carbamate (methyl) acrylate of chemical company, above-mentioned common prosperity society, such as AH- can be enumerated
600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T etc..
Above-mentioned curable resin for improve gained sealing material for liquid crystal display device cementability purpose and it is preferred that also
Contain epoxide.As above-mentioned epoxide, can enumerate for example as synthesizing above-mentioned epoxy (methyl) propylene
Epoxide, part (methyl) acrylated epoxy compound of the raw material of acid esters etc..
It should be noted that above-mentioned part (methyl) acrylated epoxy compound refers in 1 molecule in this specification
It is respectively provided with the compound of 1 or more epoxy group and 1 or more (methyl) acryloyl group, it can be for example, by making have 2 in 1 molecule
A part of epoxy group of the epoxide of a above epoxy group is reacted to obtain with (methyl) acrylic acid.
When sealing material for liquid crystal display device of the invention contains above-mentioned epoxide, preferably make above-mentioned curable resin
In (methyl) acryloyl group and epoxy group it is total in the ratio of (methyl) acryloyl group reach 30 moles of % or more and 95
Mole % or less.By making 30 moles of % or more of ratio of above-mentioned (methyl) acryloyl group, so that gained liquid crystal display
The low liquid crystal pollution of element sealant becomes more excellent.By the 95 moles of % of ratio for making above-mentioned (methyl) acryloyl group
Hereinafter, so that the cementability of gained sealing material for liquid crystal display device becomes more excellent.
From the viewpoint of further suppressing liquid crystal pollution, above-mentioned curable resin preferably have-OH base ,-NH- base ,-
NH2The hydrogen bonds unit such as base.
Sealing material for liquid crystal display device of the invention contains maleimide compound.
By using above-mentioned maleimide compound, even if sealing material for liquid crystal display device of the invention uses this hair
The bright Photoepolymerizationinitiater initiater, is also able to suppress the generation of foreign matter.
It should be noted that above-mentioned maleimide compound is not included in curable resin in the present invention.
The preferred lower limit of the molecular weight of above-mentioned maleimide compound is 400.By making above-mentioned maleimide chemical combination
The molecular weight of object is 400 or more, and gained sealing material for liquid crystal display device takes into account the curability for improving the light for long wavelength
Become more excellent with the effect for inhibiting foreign matter to generate.The more preferable lower limit of the molecular weight of above-mentioned maleimide compound is 500.
In addition, from the viewpoint of reactivity, the preferred upper limit of the molecular weight of above-mentioned maleimide compound is 1500,
The more preferable upper limit is 1000.
From the viewpoint of reactivity, above-mentioned maleimide compound is preferably to have 2 or more Malaysia acyls in 1 molecule
The multifunctional maleimide compound of imido grpup.
As above-mentioned multifunctional maleimide compound, it is preferable to use following formula (3) compound represented, following formula
(4) compound represented.
[changing 3]
In formula (3), R1Indicate the alkylidene of carbon number 2~3, the integer that n is 2~40.
[changing 4]
In formula (4), R2Indicate the divalent aliphatic group of carbon number 1~40.
In above-mentioned formula (4), R2Carbon number be preferably 12~36.In addition, R2It is preferred that having aliphatic ring.
As above-mentioned formula (4) compound represented, specifically, bis- (maleimide) fourths of such as Isosorbide-5-Nitrae-can be enumerated
Alkane, 1,20- bismaleimide -10,11- dioctyl-eicosane (following formula (5-1) compound represented), 1- heptamethylene horse
Come acid imide -2- octamethylene maleimide -4- octyl -5- heptylcyclohexane (following formula (5-2) compound represented), 1,2-
Two octamethylene maleimide -3- octyl -4- hexyl hexamethylenes (following formula (5-3) compound represented) etc..
Above-mentioned formula (4) compound represented can method for example, by recording in No. 5973166 specifications of U.S. Patent No.
Etc. synthesizing.
[changing 5]
Among above-mentioned maleimide compound, as the simple function Malaysia acyl in 1 molecule with 1 dimaleoyl imino
Group with imine moiety can enumerate such as N- biotinyl-N '-(3- maleimide propiono) -3,6- dioxaoctane -1,8-
Diamines etc..
Above-mentioned maleimide in total 100 parts by weight of above-mentioned curable resin and above-mentioned maleimide compound
The preferred lower limit of the content of compound is 2 parts by weight, preferred upper limit is 50 parts by weight.By making above-mentioned maleimide compound
Content be 2 parts by weight or more, the effect of the inhibitions foreign matter of gained sealing material for liquid crystal display device generation becomes more excellent.It is logical
Cross 50 parts by weight of content for making above-mentioned maleimide compound hereinafter, gained sealing material for liquid crystal display device photocuring
Property becomes more excellent.The more preferable lower limit of the content of above-mentioned maleimide compound is 3 parts by weight, further preferred lower limit is
5 parts by weight, particularly preferred lower limit are 10 parts by weight.The more preferable upper limit of the content of above-mentioned maleimide compound is 45 weight
Part, the further preferred upper limit are 40 parts by weight, still more preferably the upper limit is 35 parts by weight, the particularly preferred upper limit is 30 weight
Part, the most preferably upper limit are 25 parts by weight.
Sealing material for liquid crystal display device of the invention can contain thermal curing agents.
As above-mentioned thermal curing agents, such as organic acid hydrazides, imdazole derivatives, amine compounds, polynary phenol system can be enumerated
Compound, acid anhydrides etc..Wherein, it is preferable to use organic acid hydrazides.
As above-mentioned organic acid hydrazides, such as sebacic dihydrazide, isophthalic dihydrazide, adipic acid two can be enumerated
Hydrazides, acid dihydrazide etc..
As the commercially available product among above-mentioned organic acid hydrazides, the organic acid acyl of such as great Zhuo chemical company can be enumerated
Hydrazine, organic acid hydrazides of aginomoto fine chemistry corporation etc..
As the organic acid hydrazides of above-mentioned great Zhuo chemical company, can enumerate such as SDH, ADH.
As the organic acid hydrazides of above-mentioned aginomoto fine chemistry corporation, can enumerate such as AMICURE VDH,
AMICURE VDH-J, AMICURE UDH, AMICURE UDH-J etc..
Relative to total 100 parts by weight of curable resin and maleimide compound, the content of above-mentioned thermal curing agents
Preferred lower limit be 1 parts by weight, preferred upper limit is 50 parts by weight.It, can by making the content of the above-mentioned thermal curing agents range
Keep Thermocurable more excellent without deteriorating the coating etc. of gained sealing material for liquid crystal display device.Above-mentioned thermal curing agents
The more preferable upper limit of content is 30 parts by weight.
Sealing material for liquid crystal display device of the invention for the raising of viscosity, cementability based on stress dispersion effect
Improve, the improvement of linear expansivity the purpose of and preferably comprise filler.
As above-mentioned filler, inorganic filler, organic filler can be used.
As above-mentioned inorganic filler, can enumerate for example silica, talcum, bead, asbestos, gypsum, diatomite,
Terre verte, bentonite, montmorillonite, sericite, atlapulgite, aluminium oxide, zinc oxide, iron oxide, magnesia, tin oxide, titanium oxide,
Calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminium hydroxide, aluminium nitride, silicon nitride, barium sulfate, calcium silicates etc..
As above-mentioned organic filler, can enumerate for example polyester micropartical, polyurethane particulate, polyvinyl particle,
Acrylic polymer particle etc..
Above-mentioned filler may be used singly or in combination of two or more.
The preferred lower limit of the content of above-mentioned filler in 100 parts by weight of sealing material for liquid crystal display device of the invention is
10 parts by weight, preferred upper limit are 70 parts by weight.By making the content of the above-mentioned filler range, so that improving cementability
And other effects become it is more excellent without make coating etc. deteriorate.The more preferable lower limit of the content of above-mentioned filler is 20 parts by weight, more
Preferred upper limit is 60 parts by weight.
Sealing material for liquid crystal display device of the invention preferably comprises silane coupling agent.Above-mentioned silane coupling agent mainly has
As the effect for making the bonding additives of the good bondings such as sealant and substrate.
As above-mentioned silane coupling agent, it is preferable to use such as 3- TSL 8330,3- mercaptopropyi front three
Oxysilane, 3- glycidoxypropyltrime,hoxysilane, 3- isocyanate propyl trimethoxysilane etc..For them
Speech makes the excellent effect improved with the cementability of substrate etc., and is able to suppress admittedly by being chemically bonded with curable resin
The property changed resin flows out in liquid crystal.
The content of above-mentioned silane coupling agent in 100 parts by weight of sealing material for liquid crystal display device of the invention it is preferred under
It is limited to 0.1 parts by weight, preferred upper limit is 10 parts by weight.By making the content of the above-mentioned silane coupling agent range, to inhibit
The generation of liquid crystal pollution, and the effect for improving cementability becomes more excellent.The content of above-mentioned silane coupling agent it is more preferable under
It is limited to 0.3 parts by weight, the more preferable upper limit is 5 parts by weight.
Sealing material for liquid crystal display device of the invention further can contain reactive diluent, thixotroping as needed
The additives such as agent, spacer, curing accelerator, defoaming agent, levelling agent, polymerization inhibitor.
As the method for manufacturing sealing material for liquid crystal display device of the invention, can enumerate for example using homogenous disperse
The mixing machines such as device, mixer for well-distribution, omnipotent mixer, epicyclic mixer, kneader, triple-roller mill, by curable resin, the present invention
The Photoepolymerizationinitiater initiater, maleimide compound and as needed and silane coupling agent for adding etc. is mixed
Method etc..
By cooperating electrically conductive microparticle into sealing material for liquid crystal display device of the invention, led up and down so as to manufacture
Logical material.Such conductive material up and down containing sealing material for liquid crystal display device and electrically conductive microparticle of the invention is also this
One of invention.
As above-mentioned electrically conductive microparticle, metal ball can be used, be formed with conductive metal layer on the surface of resin particle
Electrically conductive microparticle etc..Wherein, the electrically conductive microparticle that conductive metal layer is formed on the surface of resin particle passes through resin particle
Excellent resilience and the ground such as transparent substrate can not be damaged and be conductively connected, so be suitble to.
The manufactured liquid crystal using sealing material for liquid crystal display device of the invention or conductive material up and down of the invention
Show that element is also one of present invention.
As the method for manufacturing liquid crystal display element of the invention, it is suitble to use liquid crystal dripping process, specifically, can arrange
It enumerates such as the method with following each process.
Liquid crystal display element can be obtained and with the method for following processes, firstly, carrying out following process: passing through silk
Wire mark brush, distributor coating etc. are in glass substrate, the PET substrate of the electrodes such as subsidiary ito thin film etc.
On one in two substrates, it is coated with sealing material for liquid crystal display device of the invention, thus form the seal pattern of frame-shaped
Process；Next, carrying out following process: in the state that sealing material for liquid crystal display device of the invention is uncured, by liquid crystal
Tiny droplets drip and be applied in the frame of the seal pattern of substrate, be overlapped the process of another substrate under vacuum；Thereafter, it carries out
Following process: via cut-off filter of 420nm etc. to the seal pattern part of sealing material for liquid crystal display device of the invention
Irradiation light, the process for thus making sealant carry out photocuring using the light of long wavelength.In addition it is also possible to make above-mentioned sealant into
On the basis of the process of row photocuring, the process for being heated and being made its heat cure to sealant is carried out.
The effect of invention
According to the present invention, it is possible to provide liquid crystal that is excellent for the curability of the light of long wavelength and being able to suppress foreign matter generation
Show element sealant.In addition, according to the present invention, it is possible to provide manufactured using the sealing material for liquid crystal display device to lead up and down
Logical material and liquid crystal display element.
Specific embodiment
It is exemplified below out embodiment, the present invention is described in more detail, but the present invention is not merely defined in these embodiments.
(production of compound shown in formula (2-1))
By by thio 87 parts by weight of xanthene -9- ketone of 2- (Carboxvmethoxv) -9H- and as monofunctional epoxy compound
To tert-butyl-phenyl glycidol ether (ADEKA corporation, " ED-509S ") 62 parts by weight in the presence of basic catalyst on one side
Stirred 48 hours with 110 DEG C makes its reaction on one side, to obtain above-mentioned formula (2-1) compound represented (m=1).As alkalinity
Catalyst has used PS-PPh3(BIOTAGE JAPAN corporation makes polystyrene (PS) support alkali obtained from triphenylphosphine
Property catalyst) 5.2 parts by weight.
It should be noted that the structure of the above-mentioned formula of gained (2-1) compound represented passes through1H-NMR、13C-NMR and FT-
IR is confirmed.
In addition, the thio xanthene -9- ketone of 2- (Carboxvmethoxv) -9H- and the match ratio to tert-butyl-phenyl glycidol ether
Example is the thio xanthene -9- ketone of 2- (Carboxvmethoxv) -9H- with molar ratio computing: to tert-butyl-phenyl glycidol ether=1: 1.
(production of compound shown in formula (2-2))
By by thio 69 parts by weight of xanthene -9- ketone of 2- hydroxyl -9H- with as monofunctional epoxy compound to tert-butyl
Phenyl glycidyl ether (ADEKA corporation, " ED-509S ") 62 parts by weight are in the presence of basic catalyst on one side with 110 DEG C
Stirring makes its reaction in 48 hours on one side, to obtain above-mentioned formula (2-2) compound represented.As basic catalyst, use
PS-PPh3(BIOTAGE JAPAN corporation makes polystyrene (PS) support basic catalyst obtained from triphenylphosphine) 5.2
Parts by weight.
It should be noted that the structure of the above-mentioned formula of gained (2-2) compound represented passes through1H-NMR、13C-NMR and FT-
IR is confirmed.
In addition, the thio xanthene -9- ketone of 2- hydroxyl -9H- with to the mixing ratio of tert-butyl-phenyl glycidol ether with mole
Than being calculated as the thio xanthene -9- ketone of 2- hydroxyl -9H-: to tert-butyl-phenyl glycidol ether=1: 1.
(Examples 1 to 9 and comparative example 1~3)
According to the match ratio recorded in table 1,2, using planetary stirring machine, (THINKY corporation, " あ ゎ と り practices too
Youth ") each material is mixed after, and then mixed using triple-roller mill, to prepare Examples 1 to 9 and comparative example 1~3
Sealing material for liquid crystal display device.
It should be noted that reaching 0.1mg/ for Photoepolymerizationinitiater initiater used in embodiment and comparative example with concentration
After the mode of mL is dissolved in acrylonitrile, wavelength is measured using spectrophotometer (Hitachi's high and new technology corporation, " U-3900 ")
Absorptivity at 430nm.Show the result in table 1,2.
In addition, the dimaleimide for the polytetramethylene ether diol recorded as maleimide compound and in table
Acetic acid esters (DIC corporation, " LUMICURE MIA200 ") is above-mentioned formula (3) compound represented.
<evaluation>
For each sealing material for liquid crystal display device obtained in embodiment and comparative example, following evaluations are carried out.By result
It is shown in table 1,2.
(photo-curable)
It is dispersed in spacer particle (ponding chemical industrial company system, " Micropearl SI-H050 ") 1 parts by weight logical
Cross embodiment and 100 parts by weight of each sealing material for liquid crystal display device that comparative example obtains in.Then, by sealant fill to point
In the syringe (Musashi Engineering corporation, " PSY-10E ") of adapted, after carrying out deaeration processing, distributor is utilized
(Musashi Engineering corporation, " SHOTMASTER300 ") is coated on the glass substrate.On the substrate using true
Empty laminating apparatus is bonded the glass substrate with size under the decompression of 5Pa.Using metal halide lamp to the glass base being bonded
The sealant partial illumination 100mW/cm of plate2Light 10 seconds.Illumination injects the case where having gone without 420nm cut-off filter and has
Both forms of the case where 420nm cut-off filter.
It is sealed the FT-IR measurement of agent using infrared spectroscopy device (BIORAD corporation, " FTS3000 "), measures source
From variable quantity of the peak of (methyl) acryloyl group before and after light irradiation, the evaluation of curability is thus carried out.Certainly by light irradiation opisthogenesis
The case where situation that the peak of (methyl) acryloyl group reduces 80% or more is denoted as " ◎ ", will reduce 70% more than and less than 80% is remembered
The case where making "○", reducing 50% more than and less than 70% is denoted as " △ ", is originated from (methyl) acryloyl group after light is irradiated
Peak reduction less than 50% the case where be denoted as "×", to evaluate photo-curable.
(preventing foreign body)
It is dispersed in spacer particle (ponding chemical industrial company system, " Micropearl SI-H050 ") 1 parts by weight logical
Cross embodiment and 100 parts by weight of each sealing material for liquid crystal display device that comparative example obtains in, place 3 in the underface of fluorescent lamp
Hour.Then, sealant is filled to the syringe of distribution (Musashi Engineering corporation, " PSY-10E ")
In, after carrying out deaeration processing, it is coated on using distributor (Musashi Engineering corporation, " SHOTMASTER300 ")
On glass substrate.The glass substrate with size is bonded under the decompression of 5Pa using vacuum forming apparatus on the substrate.At this point,
If producing foreign matter in sealant when being previously placed in immediately below fluorescent lamp, which can be sandwiched between substrate, thus generate
Bad gap.
Confirm be bonded substrate, "○" will be denoted as the case where not generating bad gap completely, will slightly generate gap not
Good situation is denoted as " △ ", obvious the case where generating bad gap will be denoted as "×", thus evaluation prevent it is foreign body.
[table 1]
[table 2]
Industrial availability
According to the present invention, it is possible to provide liquid crystal that is excellent for the curability of the light of long wavelength and being able to suppress foreign matter generation
Show element sealant.In addition, according to the present invention, it is possible to provide manufactured using the sealing material for liquid crystal display device to lead up and down
Logical material and liquid crystal display element.
Claims (8)
1. a kind of sealing material for liquid crystal display device, which is characterized in that it contains curable resin, Photoepolymerizationinitiater initiater and Malaysia
Imide compound,
Absorptivity of the Photoepolymerizationinitiater initiater at wavelength 430nm is 0.8 × 102ML/gcm or more.
2. sealing material for liquid crystal display device according to claim 1, wherein Photoepolymerizationinitiater initiater is with following formula
(1) compound of structure shown in,
In formula (1), * is bonding position.
3. sealing material for liquid crystal display device according to claim 2, wherein the compound with structure shown in formula (1)
It is the compound with structure shown in 1 formula (1) in 1 molecule.
4. sealing material for liquid crystal display device according to claim 3, wherein the compound with structure shown in formula (1)
For following formula (2-1) compound represented and/or following formula (2-2) compound represented,
In formula (2-1), (2-2), R is the structure from monofunctional epoxy compound；In formula (2-1), m be 1~5 integer.
5. sealing material for liquid crystal display device according to claim 1,2,3 or 4, wherein maleimide compound is
With the multifunctional maleimide compound of 2 or more dimaleoyl iminos in 1 molecule.
6. according to claim 1, sealing material for liquid crystal display device described in 2,3,4 or 5, wherein maleimide compound
Molecular weight be 400 or more.
7. it is a kind of up and down conductive material, containing sealing material for liquid crystal display device described in claim 1,2,3,4,5 or 6 with
And electrically conductive microparticle.
8. a kind of liquid crystal display element is using sealing material for liquid crystal display device described in claim 1,2,3,4,5 or 6
Or it is as claimed in claim 7 up and down conductive material and it is manufactured.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| JP2017-138032 | 2017-07-14 | ||
| JP2017138032 | 2017-07-14 | ||
| PCT/JP2018/025999 WO2019013194A1 (en) | 2017-07-14 | 2018-07-10 | Sealing agent for liquid crystal display elements, vertically conducting material and liquid crystal display element |
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| Publication Number | Publication Date |
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| CN110226120A true CN110226120A (en) | 2019-09-10 |
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| JP (1) | JP7156946B2 (en) |
| KR (1) | KR102612646B1 (en) |
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| JP2015231985A (en) * | 2014-05-13 | 2015-12-24 | 積水化学工業株式会社 | Modified dialkylamino benzoic acid-based compound, modified thioxanthone derivative, photocurable resin composition, sealant for liquid crystal display element, vertical conducting material, and liquid crystal display element |
| JP2017110120A (en) * | 2015-12-17 | 2017-06-22 | 三井化学株式会社 | Photocurable resin composition, display element sealing agent and liquid crystal display panel and method for manufacturing the same |
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| 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 |
| KR100906926B1 (en) | 2001-05-16 | 2009-07-10 | 세키스이가가쿠 고교가부시키가이샤 | Curing Resin Composition and Sealants and End-Sealing Materials for Displays |
| JP4702594B2 (en) * | 2004-12-21 | 2011-06-15 | Ｄｉｃ株式会社 | Photocurable composition for liquid crystal panel seal and liquid crystal panel |
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2018
- 2018-07-10 KR KR1020197015190A patent/KR102612646B1/en active IP Right Grant
- 2018-07-10 JP JP2018540897A patent/JP7156946B2/en active Active
- 2018-07-10 WO PCT/JP2018/025999 patent/WO2019013194A1/en active Application Filing
- 2018-07-10 CN CN201880007538.1A patent/CN110226120A/en active Pending
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|---|---|---|---|---|
| CN101369098A (en) * | 2003-06-04 | 2009-02-18 | 积水化学工业株式会社 | Curing resin composition, sealing material for liquid crystal display device and liquid crystal display device |
| US20120046376A1 (en) * | 2009-05-18 | 2012-02-23 | Agfa Graphics Nv | Polymerizable polymeric photoinitiators and radiation curable compositions |
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| JP7156946B2 (en) | 2022-10-19 |
| JPWO2019013194A1 (en) | 2020-05-07 |
| KR102612646B1 (en) | 2023-12-11 |
| KR20200026785A (en) | 2020-03-11 |
| TWI766068B (en) | 2022-06-01 |
| WO2019013194A1 (en) | 2019-01-17 |
| TW201908454A (en) | 2019-03-01 |
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