TWI813690B - Sealant for liquid crystal display element, upper and lower conduction material, and liquid crystal display element - Google Patents
Sealant for liquid crystal display element, upper and lower conduction material, and liquid crystal display element Download PDFInfo
- Publication number
- TWI813690B TWI813690B TW108117483A TW108117483A TWI813690B TW I813690 B TWI813690 B TW I813690B TW 108117483 A TW108117483 A TW 108117483A TW 108117483 A TW108117483 A TW 108117483A TW I813690 B TWI813690 B TW I813690B
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- Prior art keywords
- meth
- liquid crystal
- crystal display
- acrylate
- sealant
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 122
- 239000000565 sealant Substances 0.000 title claims abstract description 54
- 239000000463 material Substances 0.000 title description 4
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- 150000004292 cyclic ethers Chemical group 0.000 claims abstract description 18
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 13
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- -1 (meth)acrylic acid compound Chemical class 0.000 claims description 91
- 238000007789 sealing Methods 0.000 claims description 41
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical group C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 2
- 239000000758 substrate Substances 0.000 abstract description 47
- 230000035699 permeability Effects 0.000 abstract description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract description 16
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- 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
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 1
- YKVIWISPFDZYOW-UHFFFAOYSA-N 6-Decanolide Chemical compound CCCCC1CCCCC(=O)O1 YKVIWISPFDZYOW-UHFFFAOYSA-N 0.000 description 1
- CUXGDKOCSSIRKK-UHFFFAOYSA-N 7-methyloctyl prop-2-enoate Chemical compound CC(C)CCCCCCOC(=O)C=C CUXGDKOCSSIRKK-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- LJZSVQJYEPVJLB-UHFFFAOYSA-N C(#N)C(CCC(=O)O)C.C(#N)C(CCC(=O)O)C.[N] Chemical compound C(#N)C(CCC(=O)O)C.C(#N)C(CCC(=O)O)C.[N] LJZSVQJYEPVJLB-UHFFFAOYSA-N 0.000 description 1
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- QMFJYNOVTQYLTA-UHFFFAOYSA-N CCCCCCCCCCC.N=C=O.N=C=O.N=C=O Chemical class CCCCCCCCCCC.N=C=O.N=C=O.N=C=O QMFJYNOVTQYLTA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- VWYHWAHYVKZKHI-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC(N)=CC=C1C1=CC=C(N)C=C1 Chemical compound N=C=O.N=C=O.C1=CC(N)=CC=C1C1=CC=C(N)C=C1 VWYHWAHYVKZKHI-UHFFFAOYSA-N 0.000 description 1
- XUDHNBXOPCUCHF-UHFFFAOYSA-N N=C=O.N=C=O.OC(CC(CC1)C2)C12O Chemical compound N=C=O.N=C=O.OC(CC(CC1)C2)C12O XUDHNBXOPCUCHF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene 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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-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
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-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
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229920006127 amorphous resin Polymers 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011324 bead Substances 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
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 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
- 230000000903 blocking effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 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
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical class [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 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
- 230000007547 defect Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 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
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 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
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 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
- 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-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
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate 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
- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007650 screen-printing Methods 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
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000000475 sunscreen effect Effects 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
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-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
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
Abstract
本發明之目的在於提供一種對可撓性基板之接著性、防透濕性、及低液晶污染性優異之液晶顯示元件用密封劑。又，本發明之目的在於提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 本發明係一種液晶顯示元件用密封劑，其含有硬化性樹脂、熱塑性樹脂及聚合起始劑，且上述硬化性樹脂包含：具有5員環以上之環狀醚骨架之單官能(甲基)丙烯酸化合物、及多官能(甲基)丙烯酸化合物。An object of the present invention is to provide a sealant for liquid crystal display elements that is excellent in adhesion to a flexible substrate, moisture permeability prevention, and low liquid crystal contamination. Furthermore, an object of the present invention is to provide an upper and lower conductive material and a liquid crystal display element using the sealant for liquid crystal display elements. The present invention is a sealant for liquid crystal display elements, which contains a curable resin, a thermoplastic resin and a polymerization initiator, and the curable resin contains: monofunctional (meth)acrylic acid with a cyclic ether skeleton of 5 or more members. compounds, and multifunctional (meth)acrylic compounds.
Description
本發明係關於一種對可撓性基板之接著性、防透濕性、及低液晶污染性優異之液晶顯示元件用密封劑。又，本發明係關於一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。The present invention relates to a sealant for liquid crystal display elements that is excellent in adhesion to a flexible substrate, moisture permeability prevention, and low liquid crystal contamination. Furthermore, the present invention relates to an upper and lower conductive material and a liquid crystal display element using the sealant for liquid crystal display elements.
近年來，作為液晶顯示單元等液晶顯示元件之製造方法，就產距時間縮短，液晶用量之最佳化等觀點而言，利用如專利文獻1、專利文獻2中所揭示之使用光熱併用硬化型密封劑之被稱為滴下法之液晶滴加方式。 於滴下法中，首先，藉由滴塗而於2片附電極之透明基板之一片形成框狀之密封圖案。繼而，於密封劑未硬化之狀態下將液晶之微小液滴滴加至透明基板之框內整個面，立刻貼合另一透明基板，並對密封部照射紫外線等光進行暫時硬化。其後，液晶退火時加熱而進行正式硬化，從而製作液晶顯示元件。若於減壓下進行基板之貼合，則能夠以極高之效率製造液晶顯示元件，目前，該滴下法成為液晶顯示元件之製造方法之主流。In recent years, as a manufacturing method of liquid crystal display elements such as liquid crystal display units, from the viewpoint of shortening the lead time and optimizing the amount of liquid crystal, a curing type using a combination of light and heat as disclosed in Patent Document 1 and Patent Document 2 has been used. The method of adding sealant to liquid crystal is called the dripping method. In the dropping method, first, a frame-shaped sealing pattern is formed on one of two transparent substrates with electrodes by dropping coating. Then, while the sealant is not yet cured, tiny droplets of liquid crystal are dropped onto the entire surface of the frame of the transparent substrate, another transparent substrate is immediately attached, and the sealing portion is irradiated with light such as ultraviolet light to temporarily cure. Thereafter, the liquid crystal is heated during annealing to perform formal hardening, thereby producing a liquid crystal display element. If the substrates are bonded under reduced pressure, liquid crystal display elements can be manufactured with extremely high efficiency. Currently, the dropping method has become the mainstream method of manufacturing liquid crystal display elements.
過去，作為液晶顯示元件之基板，主要使用玻璃基板，但近年來，使用聚對苯二甲酸乙二酯、聚醯亞胺、三乙醯纖維素等之可撓性基板受到關注。然而，於習知密封劑中，存在於使用此種可撓性基板之情形時無法充分接著之問題。又，近年來，將面板彎曲而成之曲面顯示器受到關注，但於習知密封劑中，存在將基板彎曲時密封劑無法追隨而導致容易產生顯示不良之問題。 [先前技術文獻] [專利文獻]In the past, glass substrates were mainly used as substrates for liquid crystal display elements. However, in recent years, flexible substrates using polyethylene terephthalate, polyimide, triacetyl cellulose, etc. have attracted attention. However, conventional sealants have a problem of insufficient adhesion when using such a flexible substrate. In addition, in recent years, curved displays formed by bending panels have attracted attention. However, conventional sealants have a problem that the sealant cannot follow the substrate when the substrate is bent, resulting in display defects easily occurring. [Prior technical literature] [Patent Document]
專利文獻1：日本特開2001-133794號公報 專利文獻2：日本特開平5-295087號公報Patent Document 1: Japanese Patent Application Publication No. 2001-133794 Patent Document 2: Japanese Patent Application Laid-Open No. 5-295087
[發明所欲解決之課題][Problem to be solved by the invention]
本發明係關於一種對可撓性基板之接著性、防透濕性、及低液晶污染性優異之液晶顯示元件用密封劑。又，本發明之目的在於：提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。 [解決課題之技術手段]The present invention relates to a sealant for liquid crystal display elements that is excellent in adhesion to a flexible substrate, moisture permeability prevention, and low liquid crystal contamination. Furthermore, an object of the present invention is to provide an upper and lower conductive material and a liquid crystal display element using the sealant for liquid crystal display elements. [Technical means to solve the problem]
本發明係一種液晶顯示元件用密封劑，其含有硬化性樹脂、熱塑性樹脂及聚合起始劑，且上述硬化性樹脂包含：具有5員環以上之環狀醚骨架之單官能(甲基)丙烯酸化合物、及多官能(甲基)丙烯酸化合物。 以下，對本發明詳細敘述。The present invention is a sealant for liquid crystal display elements, which contains a curable resin, a thermoplastic resin and a polymerization initiator, and the curable resin contains: monofunctional (meth)acrylic acid with a cyclic ether skeleton of 5 or more members. compounds, and multifunctional (meth)acrylic compounds. Hereinafter, the present invention will be described in detail.
本發明者對在密封劑中摻合熱塑性樹脂以使液晶顯示元件用密封劑與可撓性基板對應進行了研究。然而，所獲得之密封劑相對於由聚對苯二甲酸乙二酯（PET）等所構成之基板而言，儘管觀察到某程度之接著性提高之效果，但對於尤其是由聚醯亞胺（PI）或三乙醯纖維素（TAC）所構成之基板而言，其接著性仍不足。因此，本發明者進一步對組合使用具有特定之結構之單官能(甲基)丙烯酸化合物與多官能(甲基)丙烯酸化合物作為硬化性樹脂進行了研究。其結果發現：可獲得對可撓性基板之接著性優異之液晶顯示元件用密封劑，從而完成本發明。 又，本發明之液晶顯示元件用密封劑之防透濕性及低液晶污染性亦可變得優異。The present inventors conducted research on blending a thermoplastic resin into a sealant so that the sealant for a liquid crystal display element can be adapted to a flexible substrate. However, although the obtained sealant has a certain degree of adhesion-improving effect compared to a substrate made of polyethylene terephthalate (PET) or the like, it is particularly weak for substrates made of polyimide. For substrates composed of (PI) or triacetyl cellulose (TAC), the adhesion is still insufficient. Therefore, the present inventors further conducted research on the combined use of a monofunctional (meth)acrylic compound and a polyfunctional (meth)acrylic compound having a specific structure as a curable resin. As a result, they found that a sealing agent for a liquid crystal display element excellent in adhesion to a flexible substrate can be obtained, and completed the present invention. In addition, the sealant for liquid crystal display elements of the present invention can also be excellent in moisture permeability prevention and low liquid crystal contamination properties.
本發明之液晶顯示元件用密封劑含有硬化性樹脂。 上述硬化性樹脂包含：具有5員環以上之環狀醚骨架之單官能(甲基)丙烯酸化合物（以下，亦稱為「本發明之單官能(甲基)丙烯酸化合物」）。藉由包含本發明之單官能(甲基)丙烯酸化合物作為上述硬化性樹脂，且含有下述熱塑性樹脂，本發明之液晶顯示元件用密封劑之對可撓性基板之接著性優異，即便將基板彎曲時亦可保持充分之接著力。 再者，於本說明書中，上述「(甲基)丙烯酸」係指丙烯酸或甲基丙烯酸，上述「(甲基)丙烯酸化合物」係指具有(甲基)丙烯醯基之化合物，上述「(甲基)丙烯醯基」係指丙烯醯基或甲基丙烯醯基。又，上述「單官能(甲基)丙烯酸化合物」係指於1分子中具有1個(甲基)丙烯醯基之化合物，上述「多官能(甲基)丙烯酸化合物」係指於1分子中具有2個以上之(甲基)丙烯醯基之化合物。The sealing compound for liquid crystal display elements of the present invention contains curable resin. The curable resin includes a monofunctional (meth)acrylic compound having a cyclic ether skeleton of 5 or more members (hereinafter, also referred to as the "monofunctional (meth)acrylic compound of the present invention"). By containing the monofunctional (meth)acrylic compound of the present invention as the above-mentioned curable resin and containing the following thermoplastic resin, the sealing compound for liquid crystal display elements of the present invention has excellent adhesion to a flexible substrate even if the substrate is Sufficient bonding force can be maintained even when bending. Furthermore, in this specification, the above-mentioned "(meth)acrylic acid" refers to acrylic acid or methacrylic acid, the above-mentioned "(meth)acrylic acid compound" refers to a compound having a (meth)acrylyl group, and the above-mentioned "(meth)acrylic acid compound" refers to a compound having a (meth)acrylyl group. "Basic) acrylic group" refers to acrylic group or methacrylic group. In addition, the above-mentioned "monofunctional (meth)acrylic compound" refers to a compound having one (meth)acrylyl group in one molecule, and the above-mentioned "polyfunctional (meth)acrylic compound" refers to a compound having one (meth)acrylyl group in one molecule. Compounds with more than 2 (meth)acrylyl groups.
本發明之單官能(甲基)丙烯酸化合物具有5員環以上之環狀醚骨架（以下，亦簡稱為「環狀醚骨架」）。上述環狀醚骨架較佳為碳數4以上之環狀醚骨架。上述環狀醚骨架之碳數之上限並不特別存在，但實質之上限為6。The monofunctional (meth)acrylic acid compound of the present invention has a cyclic ether skeleton with 5 or more members (hereinafter, also referred to as "cyclic ether skeleton"). The above-mentioned cyclic ether skeleton is preferably a cyclic ether skeleton having 4 or more carbon atoms. There is no particular upper limit for the number of carbon atoms in the cyclic ether skeleton, but the substantial upper limit is 6.
上述環狀醚骨架較佳為選自由四氫呋喃骨架、1,3-二㗁烷骨架、1,4-二㗁烷骨架、1,2-氧硫雜環戊烷（1,2-oxathiolane）骨架、及嗎福林骨架所組成之群中之至少1種。The above-mentioned cyclic ether skeleton is preferably selected from the group consisting of tetrahydrofuran skeleton, 1,3-dioxane skeleton, 1,4-dioxane skeleton, 1,2-oxathiolane skeleton, and at least 1 species in the group consisting of the mofolin skeleton.
本發明之單官能(甲基)丙烯酸化合物可為於1分子中具有1個上述環狀醚骨架者，亦可為具有2個以上者，但較佳為於1分子中具有1個上述環狀醚骨架者。 又，本發明之單官能(甲基)丙烯酸化合物較佳為於分子鏈之末端具有上述環狀醚骨架。The monofunctional (meth)acrylic acid compound of the present invention may have one of the above-mentioned cyclic ether skeletons in one molecule, or may have two or more, but preferably has one of the above-mentioned cyclic ether skeletons in one molecule. Ether skeleton. Furthermore, the monofunctional (meth)acrylic acid compound of the present invention preferably has the above-mentioned cyclic ether skeleton at the end of the molecular chain.
作為本發明之單官能(甲基)丙烯酸化合物，具體而言，例如可列舉：(甲基)丙烯酸四氫糠酯、由下述式（1）所表示之化合物、5-乙基-5-((甲基)丙烯醯氧基甲基)-1,3-二㗁烷等。Specific examples of the monofunctional (meth)acrylic compound of the present invention include: (meth)acrylic acid tetrahydrofurfuryl ester, a compound represented by the following formula (1), and 5-ethyl-5- ((Meth)acrylyloxymethyl)-1,3-dioxane, etc.
式（1）中，n為1以上且6以下之整數。In formula (1), n is an integer from 1 to 6.
本發明之單官能(甲基)丙烯酸化合物與下述多官能(甲基)丙烯酸化合物之合計100重量份中，本發明之單官能(甲基)丙烯酸化合物的含量之較佳之下限為3重量份，較佳之上限為95重量份。藉由本發明之單官能(甲基)丙烯酸化合物的含量為3重量份以上，所獲得之液晶顯示元件用密封劑之對可撓性基板之接著性更優異。藉由本發明之單官能(甲基)丙烯酸化合物的含量為95重量份以下，所獲得之液晶顯示元件用密封劑之防透濕性及低液晶污染性更優異。本發明之單官能(甲基)丙烯酸化合物的含量之更佳之下限為8重量份，更佳之上限為80重量份，進而較佳之下限為20重量份，進而較佳之上限為65重量份，尤佳之上限為60重量份。In the total 100 parts by weight of the monofunctional (meth)acrylic compound of the present invention and the following polyfunctional (meth)acrylic compound, the preferred lower limit of the content of the monofunctional (meth)acrylic compound of the present invention is 3 parts by weight. , the preferred upper limit is 95 parts by weight. When the content of the monofunctional (meth)acrylic compound of the present invention is 3 parts by weight or more, the sealing compound for a liquid crystal display element obtained has more excellent adhesion to the flexible substrate. When the content of the monofunctional (meth)acrylic compound of the present invention is 95 parts by weight or less, the sealant for liquid crystal display elements obtained is more excellent in anti-moisture permeability and low liquid crystal contamination properties. A more preferred lower limit of the content of the monofunctional (meth)acrylic acid compound of the present invention is 8 parts by weight, a more preferred upper limit is 80 parts by weight, a further preferred lower limit is 20 parts by weight, and a further preferred upper limit is 65 parts by weight, especially The upper limit is 60 parts by weight.
上述硬化性樹脂包含多官能(甲基)丙烯酸化合物。藉由含有上述多官能(甲基)丙烯酸化合物，本發明之液晶顯示元件用密封劑成為防透濕性及低液晶污染性優異者。The above-mentioned curable resin contains a polyfunctional (meth)acrylic compound. By containing the above-mentioned polyfunctional (meth)acrylic compound, the sealing compound for liquid crystal display elements of the present invention is excellent in moisture permeability prevention and low liquid crystal contamination properties.
作為上述多官能(甲基)丙烯酸化合物，例如可列舉：多官能甲基)丙烯酸酯化合物、多官能環氧(甲基)丙烯酸酯、多官能(甲基)丙烯酸胺酯（urethane (meth)acrylate）等。其中，較佳為多官能環氧(甲基)丙烯酸酯。 再者，於本說明書中，上述「(甲基)丙烯酸酯」係指丙烯酸酯或甲基丙烯酸酯，上述「環氧(甲基)丙烯酸酯」係指使環氧化合物中之至少1個環氧基與(甲基)丙烯酸發生反應而得之化合物。Examples of the polyfunctional (meth)acrylic compound include polyfunctional meth)acrylate compounds, polyfunctional epoxy (meth)acrylate, and polyfunctional (meth)acrylate urethane (urethane (meth)acrylate). )wait. Among them, polyfunctional epoxy (meth)acrylate is preferred. In addition, in this specification, the above-mentioned "(meth)acrylate" refers to acrylate or methacrylate, and the above-mentioned "epoxy (meth)acrylate" refers to at least one epoxy compound among the epoxy compounds. Compounds obtained by the reaction of base and (meth)acrylic acid.
作為上述多官能(甲基)丙烯酸酯化合物中之2官能者，例如可列舉：1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、2-正丁基-2-乙基-1,3-丙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、環氧乙烷加成雙酚A二(甲基)丙烯酸酯、環氧丙烷加成雙酚A二(甲基)丙烯酸酯、環氧乙烷加成雙酚F二(甲基)丙烯酸酯、二羥甲基二環戊二烯基二(甲基)丙烯酸酯、環氧乙烷改質異三聚氰酸二(甲基)丙烯酸酯、2-羥基-3-(甲基)丙烯醯氧基丙基(甲基)丙烯酸酯、碳酸酯二醇二(甲基)丙烯酸酯、聚醚二醇二(甲基)丙烯酸酯、聚酯二醇二(甲基)丙烯酸酯、聚己內酯二醇二(甲基)丙烯酸酯、聚丁二烯二醇二(甲基)丙烯酸酯等。Examples of bifunctional ones among the polyfunctional (meth)acrylate compounds include 1,3-butanediol di(meth)acrylate and 1,4-butanediol di(meth)acrylate. , 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, ethylene glycol diacrylate (Meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, 2-n-butyl-2 -Ethyl-1,3-propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, neopentyl glycol Alcohol di(meth)acrylate, ethylene oxide added to bisphenol A di(meth)acrylate, propylene oxide added to bisphenol A di(meth)acrylate, ethylene oxide added to bisphenol F di(meth)acrylate, dihydroxymethyldicyclopentadienyl di(meth)acrylate, ethylene oxide modified isocyanurate di(meth)acrylate, 2-hydroxy- 3-(meth)acryloxypropyl(meth)acrylate, carbonate diol di(meth)acrylate, polyether diol di(meth)acrylate, polyester diol di(meth)acrylate base) acrylate, polycaprolactone diol di(meth)acrylate, polybutadiene diol di(meth)acrylate, etc.
又，作為上述多官能(甲基)丙烯酸酯化合物中之3官能以上者，例如可列舉：三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、環氧丙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、己內酯改質三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成異三聚氰酸三(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯、環氧丙烷加成甘油三(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、磷酸三(甲基)丙烯醯氧基乙酯、二三羥甲基丙烷四(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯等。Furthermore, examples of the polyfunctional (meth)acrylate compound having three or more functions include: trimethylolpropane tri(meth)acrylate, ethylene oxide addition trimethylolpropane tri(meth)acrylate, Meth)acrylate, propylene oxide addition to trimethylolpropane tri(meth)acrylate, caprolactone modified trimethylolpropane tri(meth)acrylate, ethylene oxide addition to isotriacrylate Polycyanate tri(meth)acrylate, glyceryl tri(meth)acrylate, propylene oxide plus glyceryl tri(meth)acrylate, neopentylerythritol tri(meth)acrylate, tri(meth)phosphate acryloyloxyethyl ester, ditrimethylolpropane tetra(meth)acrylate, neopentylerythritol tetra(meth)acrylate, dineopenterythritol penta(meth)acrylate, dioxin Pentyerythritol hexa(meth)acrylate, etc.
作為上述多官能環氧(甲基)丙烯酸酯，例如可列舉：藉由按照慣例使多官能環氧化合物與(甲基)丙烯酸於鹼性觸媒之存在下發生反應而獲得者等。Examples of the polyfunctional epoxy (meth)acrylate include those obtained by conventionally reacting a polyfunctional epoxy compound and (meth)acrylic acid in the presence of an alkaline catalyst.
作為成為用以合成上述多官能環氧(甲基)丙烯酸酯之原料之環氧化合物，例如可列舉：雙酚A型環氧化合物、雙酚F型環氧化合物、雙酚E型環氧化合物、雙酚S型環氧化合物、2,2'-二烯丙基雙酚A型環氧化合物、氫化雙酚型環氧化合物、環氧丙烷加成雙酚A型環氧化合物、間苯二酚型環氧化合物、聯苯型環氧化合物、硫醚型環氧化合物、二苯醚型環氧化合物、二環戊二烯型環氧化合物、萘型環氧化合物、酚酚醛清漆型環氧化合物、鄰甲酚酚醛清漆型環氧化合物、二環戊二烯酚醛清漆型環氧化合物、聯苯酚醛清漆型環氧化合物、萘酚酚醛清漆型環氧化合物、縮水甘油胺型環氧化合物、烷基多元醇型環氧化合物、橡膠改質型環氧化合物、縮水甘油酯化合物等。Examples of the epoxy compound used as a raw material for synthesizing the polyfunctional epoxy (meth)acrylate include bisphenol A-type epoxy compounds, bisphenol F-type epoxy compounds, and bisphenol E-type epoxy compounds. , bisphenol S type epoxy compound, 2,2'-diallyl bisphenol A type epoxy compound, hydrogenated bisphenol type epoxy compound, propylene oxide addition bisphenol A type epoxy compound, resorcinol Phenol-type epoxy compounds, biphenyl-type epoxy compounds, thioether-type epoxy compounds, diphenyl ether-type epoxy compounds, dicyclopentadiene-type epoxy compounds, naphthalene-type epoxy compounds, phenolic novolac-type epoxy compounds Compounds, o-cresol novolak type epoxy compounds, dicyclopentadiene novolak type epoxy compounds, biphenyl novolac type epoxy compounds, naphthol novolak type epoxy compounds, glycidylamine type epoxy compounds, Alkyl polyol type epoxy compounds, rubber modified epoxy compounds, glycidyl ester compounds, etc.
上述多官能(甲基)丙烯酸胺酯例如可藉由對多官能異氰酸酯化合物使具有羥基之(甲基)丙烯酸衍生物於觸媒量之錫系化合物存在下發生反應而獲得。The polyfunctional (meth)acrylic amine ester can be obtained, for example, by reacting a (meth)acrylic acid derivative having a hydroxyl group with a polyfunctional isocyanate compound in the presence of a catalytic amount of a tin-based compound.
作為上述多官能異氰酸酯化合物，例如可列舉：異佛酮二異氰酸酯、2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、六亞甲基二異氰酸酯、三甲基六亞甲基二異氰酸酯、二苯基甲烷-4,4'-二異氰酸酯（MDI）、氫化MDI、聚合MDI、1,5-萘二異氰酸酯、降莰烷二醇二異氰酸酯、聯甲苯胺二異氰酸酯、苯二甲基二異氰酸酯（XDI）、氫化XDI、離胺酸二異氰酸酯、三苯基甲烷三異氰酸酯、三(異氰酸基苯基)硫代磷酸酯、四甲基苯二甲基二異氰酸酯、1,6,11-十一烷三異氰酸酯等。Examples of the polyfunctional isocyanate compound include isophorone diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, hexamethylene diisocyanate, and trimethylhexamethylene diisocyanate. Diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymerized MDI, 1,5-naphthalene diisocyanate, norbornanediol diisocyanate, benzidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated Undecane triisocyanate, etc.
又，作為上述多官能異氰酸酯化合物，亦可使用藉由多元醇與過量之多官能異氰酸酯化合物之反應而獲得之鏈增長後之多官能異氰酸酯化合物。 作為上述多元醇，例如可列舉：乙二醇、丙二醇、甘油、山梨醇、三羥甲基丙烷、碳酸酯二醇、聚醚二醇、聚酯二醇、聚己內酯二醇等。Furthermore, as the above-mentioned polyfunctional isocyanate compound, a chain-extended polyfunctional isocyanate compound obtained by reaction of a polyol and an excess polyfunctional isocyanate compound can also be used. Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, glycerol, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol, and the like.
作為上述具有羥基之(甲基)丙烯酸衍生物，例如可列舉：單(甲基)丙烯酸羥烷基酯、二元醇之單(甲基)丙烯酸酯、三元醇之單(甲基)丙烯酸酯或二(甲基)丙烯酸酯、環氧(甲基)丙烯酸酯等。 作為上述單(甲基)丙烯酸羥烷基酯，例如可列舉：(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸4-羥基丁酯等。 作為上述二元醇，例如可列舉：乙二醇、丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、聚乙二醇等。 作為上述三元醇，例如可列舉：三羥甲基乙烷、三羥甲基丙烷、甘油等。 作為上述環氧(甲基)丙烯酸酯，例如可列舉雙酚A型環氧丙烯酸酯等。Examples of the (meth)acrylic acid derivatives having a hydroxyl group include: hydroxyalkyl mono(meth)acrylate, mono(meth)acrylate of dihydric alcohol, and mono(meth)acrylic acid of trihydric alcohol. Ester or di(meth)acrylate, epoxy (meth)acrylate, etc. Examples of the above-mentioned hydroxyalkyl mono(meth)acrylate include: (2-hydroxyethylmeth)acrylate, 2-hydroxypropyl(meth)acrylate, 2-hydroxybutyl(meth)acrylate, 4-hydroxybutyl (meth)acrylate, etc. Examples of the glycol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, polyethylene glycol, and the like. Examples of the trihydric alcohol include trimethylolethane, trimethylolpropane, glycerin, and the like. Examples of the epoxy (meth)acrylate include bisphenol A-type epoxy acrylate.
又，上述多官能(甲基)丙烯酸化合物較佳為具有內酯之開環結構。藉由上述多官能(甲基)丙烯酸化合物具有內酯之開環結構，本發明之液晶顯示元件用密封劑之對可撓性基板之接著性更優異。Furthermore, the polyfunctional (meth)acrylic compound preferably has a lactone ring-opened structure. Since the polyfunctional (meth)acrylic compound has an open-ring structure of lactone, the sealing compound for a liquid crystal display element of the present invention has further excellent adhesion to a flexible substrate.
於上述多官能(甲基)丙烯酸化合物具有內酯之開環結構之情形時，作為該內酯，例如可列舉：γ-十一酸內酯、ε-己內酯、γ-癸內酯、σ-十二酸內酯、γ-壬內酯、γ-壬內酯、γ-戊內酯、σ-戊內酯、β-丁內酯、γ-丁內酯、β-丙內酯、σ-己內酯（σ-hexalactone）、7-丁基-2-氧雜環庚酮等。其中，較佳為開環時主骨架之直鏈部分之碳數成為5～7者，更佳為ε-己內酯。上述多官能(甲基)丙烯酸化合物可具有該等中之1種內酯之開環結構，亦可具有2種以上之內酯之開環結構。When the above-mentioned polyfunctional (meth)acrylic acid compound has a ring-opened structure of a lactone, examples of the lactone include: γ-undecanoic acid lactone, ε-caprolactone, γ-decanolactone, σ-laurolactone, γ-nonalactone, γ-nonalactone, γ-valerolactone, σ-valerolactone, β-butyrolactone, γ-butyrolactone, β-propiolactone, σ-hexalactone, 7-butyl-2-oxepanone, etc. Among them, those having a carbon number of 5 to 7 in the linear portion of the main skeleton when the ring is opened are preferred, and ε-caprolactone is more preferred. The above-mentioned polyfunctional (meth)acrylic acid compound may have the ring-opened structure of one of these lactones, or may have the ring-opened structure of two or more lactones.
又，於上述多官能(甲基)丙烯酸化合物具有內酯之開環結構之情形時，該內酯之開環結構可於1分子中僅為1個，亦可成為重複結構。於上述內酯之開環結構成為重複結構之情形時，重複數之較佳之上限為5。When the polyfunctional (meth)acrylic compound has an open-ring structure of a lactone, the number of the open-ring structures of the lactone may be only one per molecule, or it may be a repeating structure. When the ring-opened structure of the above-mentioned lactone becomes a repeating structure, a preferable upper limit of the number of repeats is 5.
作為上述多官能(甲基)丙烯酸化合物中之具有內酯之開環結構者，較佳為於上述多官能環氧(甲基)丙烯酸酯之骨架中導入有內酯之開環結構者，更佳為己內酯改質環氧(甲基)丙烯酸酯，進而較佳為己內酯改質雙酚A型環氧(甲基)丙烯酸酯。Among the above-mentioned polyfunctional (meth)acrylic compounds, those having a ring-opened structure of lactone are preferably those having a ring-opened structure of lactone introduced into the skeleton of the above-mentioned polyfunctional epoxy (meth)acrylate, and more preferably Preferred is caprolactone-modified epoxy (meth)acrylate, and further preferred is caprolactone-modified bisphenol A-type epoxy (meth)acrylate.
上述多官能(甲基)丙烯酸化合物可單獨使用，亦可組合使用2種以上。The above-mentioned polyfunctional (meth)acrylic acid compounds may be used alone, or two or more types may be used in combination.
上述多官能(甲基)丙烯酸化合物之重量平均分子量之較佳之下限為800，更佳之上限為2000。藉由上述多官能(甲基)丙烯酸化合物之重量平均分子量處於該範圍，所獲得之液晶顯示元件用密封劑之對可撓性基板之接著性、塗佈性、及防透濕性更優異。 再者，於本說明書中，上述重量平均分子量係藉由凝膠滲透層析法（GPC）使用四氫呋喃作為溶劑進行測定，並利用聚苯乙烯換算而求出之值。作為藉由GPC測定利用聚苯乙烯換算所得之數量平均分子量時之管柱，例如可列舉：Shodex LF-804（昭和電工公司製造）等。The preferred lower limit of the weight average molecular weight of the above-mentioned polyfunctional (meth)acrylic acid compound is 800, and the more preferred upper limit is 2,000. When the weight average molecular weight of the polyfunctional (meth)acrylic compound is in this range, the sealing compound for a liquid crystal display element obtained is more excellent in adhesiveness to a flexible substrate, coating properties, and moisture permeability prevention properties. In addition, in this specification, the said weight average molecular weight is measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent, and it is the value calculated using polystyrene conversion. Examples of a column for measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko Co., Ltd.).
本發明之液晶顯示元件用密封劑亦可於不損害本發明之目的之範圍內，除了本發明之單官能(甲基)丙烯酸化合物及上述多官能(甲基)丙烯酸化合物以外，亦含有其他硬化性樹脂。 作為上述其他硬化性樹脂，例如可列舉本發明之單官能(甲基)丙烯酸化合物以外之其他單官能(甲基)丙烯酸化合物或環氧化合物等。The sealant for liquid crystal display elements of the present invention may also contain other hardening agents in addition to the monofunctional (meth)acrylic compound of the present invention and the above-mentioned polyfunctional (meth)acrylic compound within the scope that does not impair the object of the present invention. Sex resin. Examples of the other curable resin include monofunctional (meth)acrylic compounds other than the monofunctional (meth)acrylic compound of the present invention, epoxy compounds, and the like.
作為上述其他單官能(甲基)丙烯酸化合物，例如可列舉：單官能(甲基)丙烯酸酯化合物、單官能(甲基)丙烯醯胺化合物等。Examples of the other monofunctional (meth)acrylic compounds include monofunctional (meth)acrylate compounds, monofunctional (meth)acrylamide compounds, and the like.
作為上述單官能(甲基)丙烯酸酯化合物，例如可列舉：(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸三級丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸異癸酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸異肉豆蔻基酯、(甲基)丙烯酸硬脂基酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸二環戊烯基酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸2-乙氧基乙酯、(甲基)丙烯酸2-丁氧基乙酯、(甲基)丙烯酸2-苯氧基乙酯、甲氧基乙二醇(甲基)丙烯酸酯、甲氧基聚乙二醇(甲基)丙烯酸酯、苯氧基二乙二醇(甲基)丙烯酸酯、苯氧基聚乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸四氫糠酯、乙基卡必醇(甲基)丙烯酸酯、(甲基)丙烯酸-2,2,2 三氟乙酯、(甲基)丙烯酸2,2,3,3-四氟丙酯、(甲基)丙烯酸1H,1H,5H-八氟戊酯、(甲基)丙烯酸亞胺基酯、(甲基)丙烯酸二甲基胺基乙酯、(甲基)丙烯酸二乙基胺基乙酯、2-(甲基)丙烯醯氧基乙基琥珀酸、2-(甲基)丙烯醯氧基乙基六氫鄰苯二甲酸、鄰苯二甲酸2-(甲基)丙烯醯氧基乙基2-羥基丙酯、磷酸2-(甲基)丙烯醯氧基乙酯、(甲基)丙烯酸縮水甘油酯等。Examples of the monofunctional (meth)acrylate compound include: (methyl)acrylate, ethyl(meth)acrylate, propyl(meth)acrylate, n-butyl(meth)acrylate, (meth)acrylate Isobutyl methacrylate, tertiary butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, (meth)acrylate Isononyl acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, isomyristyl (meth)acrylate, stearyl (meth)acrylate, (meth)acrylic acid 2-hydroxyethyl ester, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, cyclohexyl (meth)acrylate, (meth)acrylate (Meth)acrylate, dicyclopentenyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxy (meth)acrylate Ethyl ester, 2-butoxyethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, methoxyethylene glycol (meth)acrylate, methoxypolyethylene glycol ( Meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxy polyethylene glycol (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, ethyl carbitol ( Meth)acrylate, (meth)acrylic acid-2,2,2 trifluoroethyl ester, (meth)acrylic acid 2,2,3,3-tetrafluoropropyl ester, (meth)acrylic acid 1H,1H,5H -Otafluoropentyl, imino(meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, 2-(meth)acrylamide Oxyethyl succinic acid, 2-(meth)acryloxyethyl hexahydrophthalic acid, 2-(meth)acryloxyethyl 2-hydroxypropyl phthalate, phosphoric acid 2 -(Meth)acryloyloxyethyl ester, (meth)acrylic acid glycidyl ester, etc.
作為上述單官能(甲基)丙烯醯胺化合物，例如可列舉二乙基(甲基)丙烯醯胺等。Examples of the monofunctional (meth)acrylamide compound include diethyl(meth)acrylamide.
關於作為上述其他硬化性樹脂之環氧化合物，可列舉與成為用以合成上述多官能環氧(甲基)丙烯酸酯之原料之環氧化合物相同者。Examples of the epoxy compound as the other curable resin include the same epoxy compounds as the raw materials for synthesizing the polyfunctional epoxy (meth)acrylate.
本發明之液晶顯示元件用密封劑含有熱塑性樹脂。 藉由包含本發明之單官能(甲基)丙烯酸化合物作為上述硬化性樹脂，且使用上述熱塑性樹脂，本發明之液晶顯示元件用密封劑之對可撓性基板之接著性優異，即便將基板彎曲時亦可保持充分之接著力。The sealing compound for liquid crystal display elements of the present invention contains a thermoplastic resin. By containing the monofunctional (meth)acrylic compound of the present invention as the curable resin and using the thermoplastic resin, the sealing compound for liquid crystal display elements of the present invention has excellent adhesion to a flexible substrate even if the substrate is bent. Sufficient adhesion can be maintained at all times.
上述熱塑性樹脂較佳為玻璃轉移溫度（以下，亦稱為「Tg」）為30℃以下。藉由上述熱塑性樹脂之Tg為30℃以下，所獲得之液晶顯示元件用密封劑之對可撓性基板之接著性更優異。上述熱塑性樹脂之Tg之更佳之上限為25℃，進而較佳之上限為21℃，進而更佳之上限為10℃，尤佳之上限為7℃，最佳之上限為4℃。 又，上述熱塑性樹脂之Tg之較佳之下限為-30℃。 再者，於本說明書中，上述玻璃轉移溫度係指藉由基於JIS K 7121之「塑膠之轉移溫度測定方法」之示差掃描熱量測定（DSC）所測定之值。The thermoplastic resin preferably has a glass transition temperature (hereinafter also referred to as "Tg") of 30°C or less. When the Tg of the thermoplastic resin is 30° C. or less, the sealing compound for a liquid crystal display element obtained has further excellent adhesion to the flexible substrate. The upper limit of Tg of the thermoplastic resin is preferably 25°C, 21°C, 10°C, 7°C, and 4°C. Moreover, the preferable lower limit of Tg of the said thermoplastic resin is -30 degreeC. In addition, in this specification, the above-mentioned glass transition temperature refers to a value measured by differential scanning calorimetry (DSC) based on the "Transition temperature measurement method of plastics" of JIS K 7121.
上述熱塑性樹脂之重量平均分子量之較佳之下限為5000，較佳之上限10萬。藉由上述熱塑性樹脂之重量平均分子量為5000以上，所獲得之液晶顯示元件用密封劑之防透濕性更優異。藉由上述熱塑性樹脂之重量平均分子量為10萬以下，所獲得之液晶顯示元件用密封劑之塗佈性及對可撓性基板之接著性更優異。上述熱塑性樹脂之重量平均分子量之更佳之下限為2萬，更佳之上限為8萬。The preferred lower limit of the weight average molecular weight of the thermoplastic resin is 5,000, and the preferred upper limit is 100,000. When the weight average molecular weight of the thermoplastic resin is 5,000 or more, the sealant for liquid crystal display elements obtained has further excellent moisture permeability prevention properties. When the weight average molecular weight of the thermoplastic resin is 100,000 or less, the sealant for a liquid crystal display element obtained is more excellent in coating properties and adhesiveness to a flexible substrate. A more preferable lower limit of the weight average molecular weight of the thermoplastic resin is 20,000, and a more preferable upper limit is 80,000.
作為上述熱塑性樹脂，例如可列舉：聚烯烴、聚酯、(甲基)丙烯酸樹脂、聚醯胺、聚胺酯、ABS樹脂、AES樹脂、AAS樹脂、MBS樹脂、陰離子/苯乙烯共聚物、苯乙烯/(甲基)丙烯酸甲酯共聚物、聚苯乙烯、聚碳酸酯、聚苯醚、苯氧樹脂等。 作為上述聚烯烴，例如可列舉：聚乙烯、聚丙烯、乙烯/乙酸乙烯酯共聚物、乙烯/(甲基)丙烯酸共聚物、乙烯/(甲基)丙烯酸甲酯共聚物、乙烯/(甲基)丙烯酸乙酯共聚物、乙烯/乙烯醇共聚物、乙烯/(甲基)丙烯酸乙酯/順丁烯二酸酐共聚物等。 作為上述(甲基)丙烯酸樹脂，例如可列舉聚(甲基)丙烯酸甲酯等。 作為上述熱塑性樹脂，其中較佳為聚酯、(甲基)丙烯酸樹脂，更佳為聚酯，進而較佳為共聚聚酯，尤佳為飽和聚酯樹脂、飽和共聚聚酯樹脂。 該等熱塑性樹脂可單獨使用，亦可組合使用2種以上。Examples of the thermoplastic resin include polyolefin, polyester, (meth)acrylic resin, polyamide, polyurethane, ABS resin, AES resin, AAS resin, MBS resin, anion/styrene copolymer, styrene/ Methyl (meth)acrylate copolymer, polystyrene, polycarbonate, polyphenylene ether, phenoxy resin, etc. Examples of the polyolefin include polyethylene, polypropylene, ethylene/vinyl acetate copolymer, ethylene/(meth)acrylic acid copolymer, ethylene/methyl (meth)acrylate copolymer, ethylene/(meth)acrylate copolymer, ) Ethyl acrylate copolymer, ethylene/vinyl alcohol copolymer, ethylene/(meth)ethyl acrylate/maleic anhydride copolymer, etc. Examples of the (meth)acrylic resin include polymethyl (meth)acrylate and the like. As the above-mentioned thermoplastic resin, polyester and (meth)acrylic resin are preferred, polyester is more preferred, copolyester is more preferred, and saturated polyester resin and saturated copolyester resin are particularly preferred. These thermoplastic resins can be used alone or in combination of two or more types.
關於上述熱塑性樹脂，為了所獲得之液晶顯示元件用密封劑之硬化物之柔軟性及強韌性更優異，較佳為非晶性樹脂，就所獲得之液晶顯示元件用密封劑之對可撓性基板之接著性更優異之方面而言，更佳為非晶性聚酯。 作為上述非晶性聚酯中之市售者，例如可列舉：Vylon300（Tg7℃、重量平均分子量約55000）、Vylon500（Tg4℃、重量平均分子量約55000）、Vylon550（Tg-15℃、重量平均分子量約60000）、Vylon560（Tg7℃、重量平均分子量約40000）、Vylon630（Tg7℃、重量平均分子量約55000）、Vylon650（Tg10℃、重量平均分子量約55000）、Vylon670（Tg7℃、重量平均分子量約80000）（均為東洋紡織公司製造）等。 再者，於本說明書中，上述「非晶性」係指藉由基於JIS K 7121之「塑膠之轉移溫度測定方法」之示差掃描熱量測定（DSC）未確認出明確之熔點波峰。Regarding the above-mentioned thermoplastic resin, in order to obtain a cured product of the sealing compound for liquid crystal display elements that has better flexibility and toughness, an amorphous resin is preferred. In terms of the flexibility of the sealing compound for liquid crystal display elements obtained, In terms of excellent adhesion to the substrate, amorphous polyester is more preferred. Examples of commercially available amorphous polyesters include Vylon300 (Tg 7°C, weight average molecular weight approximately 55,000), Vylon 500 (Tg 4°C, weight average molecular weight approximately 55,000), and Vylon 550 (Tg -15°C, weight average molecular weight). Molecular weight is about 60000), Vylon560 (Tg7℃, weight average molecular weight is about 40000), Vylon630 (Tg7℃, weight average molecular weight is about 55000), Vylon650 (Tg10℃, weight average molecular weight is about 55000), Vylon670 (Tg7℃, weight average molecular weight is about 55000), Vylon670 (Tg7℃, weight average molecular weight is about 55000) 80000) (all manufactured by Toyo Textile Co., Ltd.), etc. In addition, in this specification, the above-mentioned "amorphous" means that no clear melting point peak can be confirmed by differential scanning calorimetry (DSC) based on the "Transition temperature measurement method of plastics" of JIS K 7121.
上述硬化性樹脂與上述熱塑性樹脂之合計100重量份中之上述熱塑性樹脂的含量之較佳之下限為10重量份，較佳之上限為70重量份。藉由上述熱塑性樹脂的含量為10重量份以上，所獲得之液晶顯示元件用密封劑之對可撓性基板之接著性更優異。藉由上述熱塑性樹脂的含量為70重量份以下，所獲得之液晶顯示元件用密封劑之塗佈性及防透濕性更優異。上述熱塑性樹脂的含量之更佳之下限為20重量份，更佳之上限為60重量份。The preferred lower limit of the content of the thermoplastic resin in a total of 100 parts by weight of the above-mentioned curable resin and the above-mentioned thermoplastic resin is 10 parts by weight, and a preferred upper limit is 70 parts by weight. When the content of the thermoplastic resin is 10 parts by weight or more, the sealing compound for liquid crystal display elements obtained has more excellent adhesion to the flexible substrate. When the content of the thermoplastic resin is 70 parts by weight or less, the sealant for liquid crystal display elements obtained has better coating properties and moisture-permeability prevention properties. A more preferable lower limit of the content of the thermoplastic resin is 20 parts by weight, and a more preferable upper limit is 60 parts by weight.
本發明之液晶顯示元件用密封劑含有聚合起始劑。 作為上述聚合起始劑，例如可列舉藉由光照射而產生自由基之光自由基聚合起始劑、或藉由加熱而產生自由基之熱自由基聚合起始劑等。The sealing compound for liquid crystal display elements of the present invention contains a polymerization initiator. Examples of the polymerization initiator include a photo radical polymerization initiator that generates radicals by light irradiation, a thermal radical polymerization initiator that generates radicals by heating, and the like.
作為上述光自由基聚合起始劑，例如可列舉：二苯甲酮系化合物、苯乙酮系化合物、醯基氧化膦系化合物、二茂鈦系化合物、肟酯系化合物、安息香醚系化合物、9-氧硫口山等。 作為上述光自由基聚合起始劑，具體而言，例如可列舉：1-羥基環己基苯基酮、2-苄基-2-二甲胺基-1-(4-N-口末啉基苯基)丁酮、1,2-(二甲胺基)-2-((4-甲基苯基)甲基)-1-(4-(4-口末啉基)苯基)-1-丁酮、2,2-二甲氧基-1,2-二苯基乙烷-1-酮、雙(2,4,6-三甲基苯甲醯基)苯基氧化膦、2-甲基-1-(4-甲基噻吩基)-2-N-口末啉基丙烷-1-酮、1-(4-(2-羥基乙氧基)-苯基)-2-羥基-2-甲基-1-丙烷-1-酮、1-(4-(苯硫基)苯基)-1,2-辛二酮2-(O-苯甲醯基肟)、2,4,6-三甲基苯甲醯基二苯基氧化膦等。 上述光自由基聚合起始劑可單獨使用，亦可組合使用2種以上。Examples of the photoradical polymerization initiator include benzophenone compounds, acetophenone compounds, phosphine oxide compounds, titanocene compounds, oxime ester compounds, and benzoin ether compounds. 9-Oxosulfokou Mountain wait. Specific examples of the photoradical polymerization initiator include: 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1-(4-N-orthyl phenyl ketone) Phenyl)butanone, 1,2-(dimethylamino)-2-((4-methylphenyl)methyl)-1-(4-(4-terminyl)phenyl)-1 -Butanone, 2,2-dimethoxy-1,2-diphenylethan-1-one, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2- Methyl-1-(4-methylthienyl)-2-N-endolinylpropan-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-Trimethylbenzoyldiphenylphosphine oxide, etc. The above-mentioned photo radical polymerization initiator may be used alone, or two or more types may be used in combination.
作為上述熱自由基聚合起始劑，例如可列舉由偶氮化合物或有機過氧化物等所構成者。其中，就抑制液晶污染之觀點而言，較佳為由偶氮化合物所構成之起始劑（以下，亦稱為「偶氮起始劑」），更佳為由高分子偶氮化合物所構成之起始劑（以下，亦稱為「高分子偶氮起始劑」）。 上述熱自由基聚合起始劑可單獨使用，亦可組合使用2種以上。 再者，於本說明書中，上述「高分子偶氮化合物」係指具有偶氮基且產生可藉由熱使(甲基)丙烯醯基硬化之自由基之數量平均分子量為300以上的化合物。Examples of the thermal radical polymerization initiator include azo compounds, organic peroxides, and the like. Among them, from the viewpoint of suppressing liquid crystal contamination, an initiator composed of an azo compound (hereinafter, also referred to as an "azo initiator") is preferred, and a polymeric azo compound is more preferred. initiator (hereinafter also referred to as "polymer azo initiator"). The above-mentioned thermal radical polymerization initiator may be used alone, or two or more types may be used in combination. In addition, in this specification, the above-mentioned "polymer azo compound" refers to a compound having an azo group and a number average molecular weight of 300 or more that generates radicals capable of curing (meth)acrylyl groups by heat.
上述高分子偶氮化合物之數量平均分子量之較佳之下限為1000，較佳之上限為30萬。藉由上述高分子偶氮化合物之數量平均分子量為該範圍，可防止對液晶之不良影響，並且易於混合至硬化性樹脂中。上述高分子偶氮化合物之數量平均分子量之更佳之下限為5000，更佳之上限為10萬，進而較佳之下限為1萬，進而較佳之上限為9萬。 再者，於本說明書中，上述數量平均分子量係藉由凝膠滲透層析法（GPC）使用四氫呋喃作為溶劑進行測定，並利用聚苯乙烯換算而求出之值。作為藉由GPC測定利用聚苯乙烯換算所得之數量平均分子量時之管柱，例如可列舉：Shodex LF-804（昭和電工公司製造）等。The preferable lower limit of the number average molecular weight of the above-mentioned polymeric azo compound is 1,000, and the preferable upper limit is 300,000. By having the number average molecular weight of the above-mentioned polymeric azo compound within this range, adverse effects on the liquid crystal can be prevented and the compound can be easily mixed into the curable resin. A more preferable lower limit of the number average molecular weight of the above-mentioned polymeric azo compound is 5,000, a more preferable upper limit is 100,000, a further preferable lower limit is 10,000, and a further preferable upper limit is 90,000. In addition, in this specification, the said number average molecular weight is measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent, and it is the value calculated using polystyrene conversion. Examples of a column for measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko Co., Ltd.).
作為上述高分子偶氮化合物，例如可列舉具有多個聚環氧烷（polyalkylene oxide）或聚二甲基矽氧烷等單元經由偶氮基鍵結而成之結構者。 作為具有多個聚環氧烷等單元經由上述偶氮基鍵結而成之結構之高分子偶氮化合物，較佳為具有聚環氧乙烷結構者。 作為上述高分子偶氮化合物，具體而言，例如可列舉：4,4'-偶氮雙(4-氰基戊酸)與聚伸烷基二醇之縮聚物、或4,4'-偶氮雙(4-氰基戊酸)與具有末端胺基之聚二甲基矽氧烷之縮聚物等。 作為上述高分子偶氮起始劑中之市售者，例如可列舉：VPE-0201、VPE-0401、VPE-0601、VPS-0501、VPS-1001（均為富士膠片和光純藥公司製造）等。又，作為並非高分子之偶氮起始劑，例如可列舉：V-65、V-501（均為富士膠片和光純藥公司製造）等。Examples of the polymer azo compound include those having a structure in which a plurality of units such as polyalkylene oxide or polydimethylsiloxane are bonded via azo groups. As a polymeric azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via the above-mentioned azo group, those having a polyethylene oxide structure are preferred. Specific examples of the polymeric azo compound include: a condensation polymer of 4,4'-azobis(4-cyanovaleric acid) and polyalkylene glycol, or a 4,4'-azo compound. Condensation polymers of nitrogen bis(4-cyanovaleric acid) and polydimethylsiloxane with terminal amine groups, etc. Examples of commercially available polymeric azo initiators include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (all manufactured by Fujifilm and Wako Pure Chemical Industries, Ltd.), etc. . Examples of azo initiators that are not polymers include V-65 and V-501 (both manufactured by Fujifilm and Wako Pure Chemical Industries, Ltd.).
作為上述有機過氧化物，例如可列舉：過氧化酮、過氧縮酮、過氧化氫、二烷基過氧化物、過氧酯、二醯基過氧化物、過氧化二碳酸酯等。Examples of the organic peroxide include ketone peroxide, peroxyketal, hydrogen peroxide, dialkyl peroxide, peroxyester, diyl peroxide, peroxydicarbonate, and the like.
上述聚合起始劑之含量相對於上述硬化性樹脂100重量份，較佳之下限為0.01重量份，較佳之上限為10重量份。藉由上述聚合起始劑的含量為該範圍，所獲得之液晶顯示元件用密封劑抑制液晶污染，並且保存穩定性或硬化性更優異。上述聚合起始劑的含量之更佳之下限為0.1重量份，更佳之上限為5重量份。The content of the above-mentioned polymerization initiator has a preferable lower limit of 0.01 parts by weight and a preferable upper limit of 10 parts by weight relative to 100 parts by weight of the above-mentioned curable resin. When the content of the above-mentioned polymerization initiator is within this range, the sealing compound for a liquid crystal display element obtained suppresses liquid crystal contamination and is more excellent in storage stability or curability. A more preferable lower limit of the content of the above-mentioned polymerization initiator is 0.1 parts by weight, and a more preferable upper limit is 5 parts by weight.
本發明之液晶顯示元件用密封劑亦可含有熱硬化劑。 作為上述熱硬化劑，例如可列舉：有機醯肼、咪唑衍生物、胺化合物、多酚系化合物、酸酐等。其中，較佳為使用有機醯肼。 上述熱硬化劑可單獨使用，亦可組合使用2種以上。The sealing compound for liquid crystal display elements of the present invention may contain a thermosetting agent. Examples of the thermosetting agent include organic hydrazides, imidazole derivatives, amine compounds, polyphenol compounds, acid anhydrides, and the like. Among them, organic hydrazine is preferably used. The above-mentioned thermosetting agents may be used alone or in combination of two or more types.
作為上述有機醯肼，例如可列舉：癸二酸二醯肼、間苯二甲酸二醯肼、己二酸二醯肼、丙二酸二醯肼等。 作為上述有機醯肼中之市售者，例如可列舉：大塚化學公司製造之有機醯肼、Ajinomoto Fine-Techno公司製造之有機醯肼等。 作為上述大塚化學公司製造之有機醯肼，例如可列舉：SDH、ADH等。 作為上述Ajinomoto Fine-Techno公司製造之有機醯肼，例如可列舉：Ajicure VDH、Ajicure VDH-J、Ajicure UDH、Ajicure UDH-J等。Examples of the organic hydrazine include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like. Examples of commercially available organic hydrazides include organic hydrazides manufactured by Otsuka Chemical Co., Ltd. and organic hydrazides manufactured by Ajinomoto Fine-Techno Co., Ltd. Examples of the organic hydrazides manufactured by Otsuka Chemical Co., Ltd. include SDH, ADH, and the like. Examples of the organic hydrazine manufactured by Ajinomoto Fine-Techno include Ajicure VDH, Ajicure VDH-J, Ajicure UDH, and Ajicure UDH-J.
上述熱硬化劑之含量相對於上述硬化性樹脂100重量份，較佳之下限為1重量份，較佳之上限為50重量份。藉由上述熱硬化劑的含量為該範圍，不會使所獲得之液晶顯示元件用密封劑之塗佈性等變差，熱硬化性可更優異。上述熱硬化劑的含量之較佳之上限為30重量份。The content of the above-mentioned thermal hardener is preferably lower limit is 1 part by weight and upper limit is preferably 50 parts by weight relative to 100 parts by weight of the above-mentioned curable resin. When the content of the thermosetting agent is within this range, the coating properties of the sealing compound for liquid crystal display elements obtained will not be deteriorated, and the thermosetting properties can be further improved. The preferred upper limit of the content of the above-mentioned thermal hardener is 30 parts by weight.
本發明之液晶顯示元件用密封劑為了黏度之提高、應力分散效果之進一步之接著性之提高、線膨脹率之改善、硬化物之耐濕性之提高等，較佳為含有填充劑。The sealant for liquid crystal display elements of the present invention preferably contains a filler in order to increase the viscosity, further improve the stress dispersion effect, improve the adhesion, improve the linear expansion rate, and improve the moisture resistance of the cured product.
作為上述填充劑，可使用無機填充劑或有機填充劑。 作為上述無機填充劑，例如可列舉：二氧化矽（silica）、滑石、玻璃珠、石棉、石膏、矽藻土、膨潤石、膨土、蒙脫石、絹雲母、活性白土、氧化鋁、氧化鋅、氧化鐵、氧化鎂、氧化錫、氧化鈦、碳酸鈣、碳酸鎂、氫氧化鎂、氫氧化鋁、氮化鋁、氮化矽、硫酸鋇、矽酸鈣等。 作為上述有機填充劑，例如可列舉：聚酯微粒子、聚胺酯微粒子、乙烯聚合物微粒子、丙烯酸聚合物微粒子等。 上述填充劑可單獨使用，亦可組合使用2種以上。As the above-mentioned filler, an inorganic filler or an organic filler can be used. Examples of the inorganic filler include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, bentonite, bentonite, montmorillonite, sericite, activated clay, alumina, oxide Zinc, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate, etc. Examples of the organic filler include polyester microparticles, polyurethane microparticles, ethylene polymer microparticles, and acrylic polymer microparticles. The above-mentioned fillers may be used alone or in combination of two or more types.
本發明之液晶顯示元件用密封劑100重量份中之上述填充劑的含量之較佳之下限為10重量份，較佳之上限為70重量份。藉由上述填充劑的含量為該範圍，而不會使塗佈性等變差，接著性之改善等效果更優異。上述填充劑的含量之更佳之下限為20重量份，更佳之上限為60重量份。The preferred lower limit of the content of the above-mentioned filler in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 10 parts by weight, and the preferred upper limit is 70 parts by weight. By keeping the content of the filler within this range, the coating properties will not be deteriorated, and the effects such as improving the adhesion will be more excellent. A more preferable lower limit of the content of the above-mentioned filler is 20 parts by weight, and a more preferable upper limit is 60 parts by weight.
本發明之液晶顯示元件用密封劑亦可含有矽烷偶合劑。上述矽烷偶合劑主要具有作為用以將密封劑與基板等良好地接著之接著助劑之作用。The sealing compound for liquid crystal display elements of the present invention may also contain a silane coupling agent. The above-mentioned silane coupling agent mainly functions as an adhesion aid for satisfactorily adhering the sealant to the substrate and the like.
作為上述矽烷偶合劑，例如較佳地使用3-胺基丙基三甲氧基矽烷、3-巰丙基三甲氧基矽烷、3-縮水甘油氧基丙基三甲氧基矽烷、3-異氰酸基丙基三甲氧基矽烷等。該等提高與基板等之接著性之效果優異，可藉由與硬化性樹脂化學鍵結而抑制硬化性樹脂向液晶中流出。 上述矽烷偶合劑可單獨使用，亦可組合使用2種以上。As the silane coupling agent, for example, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, and 3-isocyanate are preferably used. Propyltrimethoxysilane, etc. These have an excellent effect of improving the adhesion with the substrate and the like, and can suppress the outflow of the curable resin into the liquid crystal by chemically bonding with the curable resin. The above-mentioned silane coupling agents may be used alone, or two or more types may be used in combination.
本發明之液晶顯示元件用密封劑100重量份中之上述矽烷偶合劑的含量之較佳之下限為0.1重量份，較佳之上限為10重量份。藉由上述矽烷偶合劑的含量為該範圍，而成為抑制液晶污染之產生並且提高接著性之效果更優異者。上述矽烷偶合劑的含量之更佳之下限為0.3重量份，更佳之上限為5重量份。The preferred lower limit of the content of the above-mentioned silane coupling agent in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 0.1 parts by weight, and the preferred upper limit is 10 parts by weight. When the content of the silane coupling agent is within this range, the effect of suppressing the generation of liquid crystal contamination and improving the adhesion becomes more excellent. A more preferable lower limit of the content of the above-mentioned silane coupling agent is 0.3 parts by weight, and a more preferable upper limit is 5 parts by weight.
本發明之液晶顯示元件用密封劑亦可含有遮光劑。藉由含有上述遮光劑，本發明之液晶顯示元件用密封劑可較佳地用作遮光密封劑。The sealing compound for liquid crystal display elements of the present invention may also contain a light-shielding agent. By containing the above-mentioned light-shielding agent, the sealing compound for liquid crystal display elements of the present invention can be preferably used as a light-shielding sealing agent.
作為上述遮光劑，例如可列舉：氧化鐵、鈦黑、苯胺黑、花青黑（cyanine black）、富勒烯、碳黑、樹脂被覆型炭黑等。其中，較佳為鈦黑。Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, resin-coated carbon black, and the like. Among them, titanium black is preferred.
上述鈦黑係與對波長300 nm以上且800 nm以下之光之平均穿透率相比較，對紫外線區域附近，尤其是對波長370 nm以上且450 nm以下之光之穿透率較高之物質。即，上述鈦黑係具有一方面藉由充分遮斷可見光區域之波長之光而對本發明之液晶顯示元件用密封劑賦予遮光性，而一方面使紫外線區域附近之波長之光穿透之性質的遮光劑。因此，藉由使用能夠利用上述鈦黑之穿透率較高之波長（370 nm以上且450 nm以下）之光開始反應者作為上述光自由基聚合起始劑或上述光陽離子聚合起始劑，可進一步增大本發明之液晶顯示元件用密封劑之光硬化性。又，另一方面，作為本發明之液晶顯示元件用密封劑中所含有之遮光劑，較佳為絕緣性較高之物質，且作為絕緣性較高之遮光劑，較佳亦為鈦黑。 上述鈦黑較佳為每1 μm之光學濃度（OD值）為3以上，更佳為4以上。上述鈦黑之遮光性越高則越佳，上述鈦黑之OD值之較佳之上限並不特別存在，但通常成為5以下。Compared with the average transmittance of light with wavelengths above 300 nm and below 800 nm, the above-mentioned titanium black is a substance with high transmittance near the ultraviolet region, especially for light with wavelengths above 370 nm and below 450 nm. . That is, the titanium black system has the property of imparting light-shielding properties to the sealing compound for liquid crystal display elements of the present invention by fully blocking light of wavelengths in the visible light range, and on the other hand, transmitting light of wavelengths near the ultraviolet range. Sunscreen. Therefore, by using as the above-mentioned photoradical polymerization initiator or the above-mentioned photocationic polymerization initiator, one capable of starting the reaction using light of a wavelength (370 nm or more and 450 nm or less) with a high transmittance of the titanium black, The photocurability of the sealing compound for liquid crystal display elements of the present invention can be further increased. On the other hand, the light-shielding agent contained in the sealing compound for liquid crystal display elements of the present invention is preferably a substance with high insulation properties, and the light-shielding agent with high insulation properties is also preferably titanium black. The above-mentioned titanium black preferably has an optical density (OD value) per 1 μm of 3 or more, more preferably 4 or more. The higher the light-shielding property of the titanium black is, the better it is. There is no particular upper limit for the OD value of the titanium black, but it is usually 5 or less.
上述鈦黑即便為未進行表面處理者，亦發揮充分之效果，但亦可使用表面經偶合劑等有機成分處理者、或由氧化矽、氧化鈦、氧化鍺、氧化鋁、氧化鋯、氧化鎂等無機成分被覆者等經表面處理後之鈦黑。其中，就可進一步提高絕緣性之方面而言，較佳為經有機成分處理者。 又，使用摻合有上述鈦黑作為遮光劑之本發明之液晶顯示元件用密封劑製造之液晶顯示元件由於具有充分的遮光性，故而可實現無光之漏出，具有較高對比度，且具有優異圖像顯示品質之液晶顯示元件。The above-mentioned titanium black can still exert sufficient effects even if it is not surface-treated. However, it can also be used if the surface is treated with organic components such as coupling agents, or it can be made of silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, or magnesium oxide. Titanium black coated with inorganic components and surface treated. Among them, those treated with organic components are preferred in terms of further improving insulation properties. In addition, the liquid crystal display element manufactured using the sealing compound for liquid crystal display elements of the present invention mixed with the above-mentioned titanium black as a light-shielding agent has sufficient light-shielding properties, so it can achieve no light leakage, has a high contrast ratio, and has excellent performance. LCD display components for image display quality.
作為上述鈦黑中之市售者，例如可列舉：三菱材料公司製造之鈦黑、赤穗化成公司製造之鈦黑等。 作為上述三菱材料公司製造之鈦黑，例可列舉：12S、13M、13M-C、13R-N、14M-C等。 作為上述赤穗化成公司製造之鈦黑，例如可列舉Tilack D等。Examples of commercially available titanium blacks include titanium black manufactured by Mitsubishi Materials Corporation, titanium black manufactured by Ako Chemicals Co., Ltd., and the like. Examples of the titanium black manufactured by Mitsubishi Materials include 12S, 13M, 13M-C, 13R-N, 14M-C, and the like. Examples of the titanium black manufactured by Ako Kasei Co., Ltd. include Tilack D and the like.
上述鈦黑之比表面積之較佳之下限為13 m2 /g，較佳之上限為30 m2 /g，更佳之下限為15 m2 /g，更佳之上限為25 m2 /g。 又，上述鈦黑之體積電阻之較佳之下限為0.5 Ω·cm，較佳之上限為3 Ω·cm，更佳之下限為1 Ω·cm，更佳之上限為2.5 Ω·cm。The preferred lower limit of the specific surface area of the titanium black is 13 m 2 /g, the preferred upper limit is 30 m 2 /g, the preferred lower limit is 15 m 2 /g, and the preferred upper limit is 25 m 2 /g. In addition, the preferred lower limit of the volume resistance of the titanium black is 0.5 Ω·cm, the preferred upper limit is 3 Ω·cm, the more preferred lower limit is 1 Ω·cm, and the more preferred upper limit is 2.5 Ω·cm.
上述遮光劑之一次粒徑只要為液晶顯示元件之基板間之距離以下，則並無特別限定，但較佳之下限為1 nm，較佳之上限為5000 nm。藉由上述遮光劑之一次粒徑為該範圍，而可成為不會使所獲得之液晶顯示元件用密封劑之塗佈性等變差並且遮光性更優異者。上述遮光劑之一次粒徑之更佳之下限為5 nm，更佳之上限為200 nm，進而較佳之下限為10 nm，進而較佳之上限為100 nm。 再者，上述遮光劑之一次粒徑可使用NICOMP 380ZLS（PARTICLE SIZING SYSTEMS公司製造）使上述遮光劑分散於溶劑（水、有機溶劑等）進行測定。The primary particle size of the above-mentioned light-shielding agent is not particularly limited as long as it is less than the distance between the substrates of the liquid crystal display element, but the preferred lower limit is 1 nm and the preferred upper limit is 5000 nm. By having the primary particle diameter of the light-shielding agent within this range, it is possible to obtain a sealing compound for a liquid crystal display element that has better light-shielding properties without deteriorating the applicability and the like. A more preferable lower limit of the primary particle size of the above-mentioned sunscreen agent is 5 nm, a more preferable upper limit is 200 nm, a further preferable lower limit is 10 nm, and a further preferable upper limit is 100 nm. In addition, the primary particle size of the above-mentioned light-shielding agent can be measured by dispersing the above-mentioned light-shielding agent in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICLE SIZING SYSTEMS).
本發明之液晶顯示元件用密封劑100重量份中之上述遮光劑的含量之較佳之下限為5重量份，較佳之上限為80重量份。藉由上述遮光劑的含量為該範圍，而不會使所獲得之液晶顯示元件用密封劑之接著性、硬化後之強度、及繪圖性大幅下降，且可發揮更優異之遮光性。上述遮光劑的含量之更佳之下限為10重量份，更佳之上限為70重量份，進而較佳之下限為30重量份，進而較佳之上限為60重量份。The preferred lower limit of the content of the above-mentioned light-shielding agent in 100 parts by weight of the sealant for liquid crystal display elements of the present invention is 5 parts by weight, and the preferred upper limit is 80 parts by weight. When the content of the above-mentioned light-shielding agent is within this range, the adhesiveness, strength after curing, and drawing properties of the sealing compound for liquid crystal display elements obtained are not significantly reduced, and more excellent light-shielding properties can be exerted. A more preferable lower limit of the content of the above-mentioned sunscreen agent is 10 parts by weight, a more preferable upper limit is 70 parts by weight, a further preferable lower limit is 30 parts by weight, and a further preferable upper limit is 60 parts by weight.
本發明之液晶顯示元件用密封劑亦可進而視需要含有應力緩和劑、反應性稀釋劑、觸變劑、間隔劑（spacer）、硬化促進劑、消泡劑、調平劑、聚合抑制劑等添加劑。The sealant for liquid crystal display elements of the present invention may further contain a stress reliever, a reactive diluent, a thixotropic agent, a spacer, a hardening accelerator, a defoaming agent, a leveling agent, a polymerization inhibitor, etc., if necessary. Additives.
作為本發明之液晶顯示元件用密封劑之製造方法，例如可列舉使用混合機將硬化性樹脂、熱塑性樹脂、聚合起始劑、及視需要而使用之矽烷偶合劑等添加劑混合之方法等。作為上述混合機，例如可列舉：勻相分散機、均質攪拌機、萬能攪拌機、行星式攪拌機、捏合機、三輥軋機等。Examples of a method for producing the sealing compound for a liquid crystal display element of the present invention include a method of mixing a curable resin, a thermoplastic resin, a polymerization initiator, and optionally additives such as a silane coupling agent using a mixer. Examples of the mixer include a homogeneous disperser, a homogeneous mixer, a universal mixer, a planetary mixer, a kneader, a three-roll mill, and the like.
藉由在本發明之液晶顯示元件用密封劑中摻合導電性微粒子，可製造上下導通材料。又，含有本發明之液晶顯示元件用密封劑及導電性微粒子之上下導通材料亦為本發明之一。By blending conductive fine particles into the sealing compound for liquid crystal display elements of the present invention, a vertical conductive material can be produced. In addition, an upper and lower conductive material containing the sealant for liquid crystal display elements of the present invention and conductive fine particles is also one of the present invention.
作為上述導電性微粒子，可使用金屬球、於樹脂微粒子之表面形成有導電金屬層者等。其中，於樹脂微粒子之表面形成有導電金屬層者由於藉由樹脂微粒子之優異之彈性而不會損傷透明基板等能夠進行導電連接，故而較佳。As the conductive fine particles, metal balls, resin fine particles having a conductive metal layer formed on their surfaces, etc. can be used. Among them, those in which a conductive metal layer is formed on the surface of the resin fine particles are preferable because they enable conductive connection without damaging the transparent substrate or the like due to the excellent elasticity of the resin fine particles.
又，使用本發明之液晶顯示元件用密封劑或本發明之上下導通材料而成之液晶顯示元件亦為本發明之一。In addition, a liquid crystal display element using the sealant for liquid crystal display elements of the present invention or the upper and lower conductive materials of the present invention is also one of the present invention.
本發明之液晶顯示元件用密封劑可較佳地用於利用液晶滴下法所進行之液晶顯示元件之製造。作為利用液晶滴下法製造本發明之液晶顯示元件之方法，例如可列舉以下方法等。 首先，進行藉由網版印刷、分注器塗佈等將本發明之液晶顯示元件用密封劑塗佈於基板而形成框狀之密封圖案之步驟。繼而，進行以下步驟：於本發明之液晶顯示元件用密封劑等為未硬化之狀態下將液晶之微小液滴滴加塗佈於密封圖案之框內整個面，立即重疊另一基板。其後，可藉由進行對密封圖案部分照射紫外線等光使密封劑光硬化之步驟之方法而獲得液晶顯示元件。又，除了進行使密封劑光硬化之步驟以外，亦可進行將密封劑加熱使其硬化之步驟。The sealant for liquid crystal display elements of the present invention can be preferably used for manufacturing liquid crystal display elements using the liquid crystal dropping method. Examples of the method for manufacturing the liquid crystal display element of the present invention using the liquid crystal dropping method include the following methods. First, a step of applying the sealant for liquid crystal display elements of the present invention to a substrate by screen printing, dispenser coating, or the like to form a frame-shaped sealing pattern is performed. Next, the following steps are performed: in a state where the sealant for liquid crystal display elements of the present invention is not hardened, tiny droplets of liquid crystal are applied dropwise to the entire surface of the frame of the sealing pattern, and another substrate is immediately overlapped. Thereafter, a liquid crystal display element can be obtained by performing a step of irradiating the sealing pattern portion with light such as ultraviolet light to photoharden the sealing agent. In addition to the step of photocuring the sealing agent, the step of heating and curing the sealing agent may also be performed.
作為上述基板，較佳為可撓性基板。 作為上述可撓性基板，例如可列舉由聚對苯二甲酸乙二酯（PET）、聚醯亞胺（PI）、三乙醯纖維素（TAC）、聚酯、聚(甲基)丙烯酸酯、聚碳酸酯、聚醚碸等所構成之基板。本發明之液晶顯示元件用密封劑即便對尤其是由聚醯亞胺（PI）或三乙醯纖維素（TAC）所構成之可撓性基板亦具有優異之接著性。 又，本發明之液晶顯示元件用密封劑亦可於接著通常之玻璃基板時使用。 通常於上述基板形成由氧化銦等所構成之透明電極、由聚醯亞胺等所構成之配向膜、無機質離子遮蔽膜等。 [發明之效果]As the above-mentioned substrate, a flexible substrate is preferred. Examples of the flexible substrate include polyethylene terephthalate (PET), polyimide (PI), triacetyl cellulose (TAC), polyester, and poly(meth)acrylate. , polycarbonate, polyether styrene, etc. The sealant for a liquid crystal display element of the present invention has excellent adhesion to a flexible substrate made particularly of polyimide (PI) or triacetyl cellulose (TAC). In addition, the sealant for liquid crystal display elements of the present invention can also be used when bonding to a normal glass substrate. Usually, a transparent electrode made of indium oxide, an alignment film made of polyimide, etc., an inorganic ion shielding film, etc. are formed on the above-mentioned substrate. [Effects of the invention]
根據本發明，可提供一種對可撓性基板之接著性、防透濕性、及低液晶污染性優異之液晶顯示元件用密封劑。又，根據本發明，可提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。According to the present invention, it is possible to provide a sealant for liquid crystal display elements that is excellent in adhesion to a flexible substrate, moisture permeability prevention, and low liquid crystal contamination. Furthermore, according to the present invention, it is possible to provide an upper and lower conductive material and a liquid crystal display element using the sealant for liquid crystal display elements.
以下，列舉實施例更詳細地對本發明進行說明，但本發明並非僅限定於該等實施例。Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited only to these examples.
（實施例1～13、比較例1～4） 按照表1、2中所記載之摻合比使用行星式攪拌機（Thinky公司製造，「去泡攪拌太郎」）將各材料混合後，進一步使用三輥軋機進行混合，藉此製備實施例1～13及比較例1～4之液晶顯示元件用密封劑。(Examples 1 to 13, Comparative Examples 1 to 4) Examples 1 to 13 were prepared by mixing each material using a planetary mixer ("Defoaming Mixer Taro" manufactured by Thinky Corporation) according to the mixing ratios described in Tables 1 and 2, and further mixing using a three-roll mill. and the sealing compounds for liquid crystal display elements of Comparative Examples 1 to 4.
＜評價＞ 對實施例及比較例中所獲得之液晶顯示元件用密封劑進行以下評價。將結果示於表1、2。＜Evaluation＞ The sealing compounds for liquid crystal display elements obtained in Examples and Comparative Examples were evaluated as follows. The results are shown in Tables 1 and 2.
（對PET基板之接著性） 將實施例及比較例中所獲得之各液晶顯示元件用密封劑以成為25 mm之寬度且厚度40 μm之方式塗佈於25 mm×60 mm的聚對苯二甲酸乙二酯（PET）膜（Lintec公司製造，「PET5011」）而製作試驗片。使用拉伸試驗機（島津製作所公司製造，「EZ Graph」）於25℃、剝離速度300 mm/min之條件對所獲得之試驗片測定180度剝離強度。 將180度剝離強度為10 N/cm以上者設為「◎」，將5 N/cm以上且未達10 N/cm者設為「○」，將2 N/cm以上且未達5 N/cm者設為「Δ」，將未達2 N/cm者設為「×」來評價對PET基板之接著性。(Adhesion to PET substrate) The sealant for each liquid crystal display element obtained in the Examples and Comparative Examples was applied to a 25 mm × 60 mm polyethylene terephthalate (PET) film so that the width was 25 mm and the thickness was 40 μm. (manufactured by Lintec Corporation, "PET5011") to prepare test pieces. The 180-degree peel strength of the obtained test piece was measured using a tensile testing machine ("EZ Graph" manufactured by Shimadzu Corporation) at 25°C and a peeling speed of 300 mm/min. The 180-degree peel strength is rated as "◎" if it is 10 N/cm or more, "○" is if it is 5 N/cm or more and less than 10 N/cm, and "○" is if it is 2 N/cm or more and less than 5 N/cm. cm was regarded as "Δ", and those less than 2 N/cm were regarded as "×" to evaluate the adhesion to the PET substrate.
（對TAC基板之接著性） 將實施例及比較例中所獲得之各液晶顯示元件用密封劑以成為25 mm之寬度且厚度40 μm之方式塗佈於25 mm×60 mm之三乙醯纖維素（TAC）膜（富士軟片公司製造，「TD80UL」）而製作試驗片。使用拉伸試驗機（島津製作所公司製造，「EZ Graph」）於25℃、剝離速度300 mm/min之條件對所獲得之試驗片測定180度剝離強度。 將180度剝離強度為10 N/cm以上者設為「◎」，將5 N/cm以上且未達10 N/cm者設為「○」，將2 N/cm以上且未達5 N/cm者設為「Δ」，將未達2 N/cm者設為「×」來評價對TAC基板之接著性。(Adhesion to TAC substrate) The sealant for each liquid crystal display element obtained in the Examples and Comparative Examples was applied to a 25 mm × 60 mm triacetyl cellulose (TAC) film (Fuji Film) so that the width was 25 mm and the thickness was 40 μm. company, "TD80UL") to produce test pieces. The 180-degree peel strength of the obtained test piece was measured using a tensile testing machine ("EZ Graph" manufactured by Shimadzu Corporation) at 25°C and a peeling speed of 300 mm/min. The 180-degree peel strength is rated as "◎" if it is 10 N/cm or more, "○" is if it is 5 N/cm or more and less than 10 N/cm, and "○" is if it is 2 N/cm or more and less than 5 N/cm. cm was regarded as "Δ", and those less than 2 N/cm were regarded as "×" to evaluate the adhesion to the TAC substrate.
（防透濕性） 使用塗佈機將實施例及比較例中所獲得之各液晶顯示元件用密封劑以成為厚度200～300 μm之方式塗佈於平滑之脫模膜上。繼而，藉由使用金屬鹵素燈照射100 mW/cm2 之紫外線30秒而獲得透濕度測定用膜。藉由按照JIS Z 0208之防濕包裝材料之透濕度試驗方法（杯式法）之方法製作透濕度試驗用杯，安裝所獲得之透濕度測定用膜，放入至60℃、90%RH之恆溫恆濕烘箱中測定透濕度。將所獲得之透濕度之值未達500 g/m2 ·24hr之情形設為「○」，將500 g/m2 ·24hr以上且未達800 g/m2 ·24hr之情形設為「Δ」，將800 g/m2 ·24hr以上之情形設為「×」來評價防透濕性。(Anti-moisture permeability) The sealant for liquid crystal display elements obtained in Examples and Comparative Examples was applied on a smooth release film using a coater so that the thickness would be 200 to 300 μm. Next, a film for moisture permeability measurement was obtained by irradiating ultraviolet light of 100 mW/cm 2 for 30 seconds using a metal halide lamp. Make a moisture permeability test cup in accordance with JIS Z 0208 moisture permeability test method for moisture-proof packaging materials (cup method), attach the obtained moisture permeability measurement film, and place it in a room at 60°C and 90%RH. The moisture permeability was measured in a constant temperature and humidity oven. When the obtained moisture permeability value is less than 500 g/m 2 ·24hr, it is regarded as "○", and when it is more than 500 g/m 2 ·24hr and less than 800 g/m 2 ·24hr, it is regarded as "Δ" ”, and the case of 800 g/m 2 ·24hr or more was regarded as “×” to evaluate the moisture permeability prevention property.
（低液晶污染性） 使1重量份之間隔微粒子（積水化學工業公司製造，「Micropearl SI-H050」）分散於100重量份之實施例及比較例中所獲得之各液晶顯示元件用密封劑。繼而，將分散有間隔微粒子之密封劑填充於滴塗用之注射器（武藏高科技公司製造，「PSY-10E」）而進行脫泡處理。利用分注器（武藏高科技公司製造，「SHOTMASTER300」）將脫泡處理後之密封劑以線寬成為1 mm的方式塗佈於2片摩擦完成之配向膜及透明帶電極之TAC膜（富士軟片公司製造，「TD80UL」）之1片。 繼而，將液晶（Chisso公司製造，「JC-5004LA」）之微小液滴滴加塗佈於TAC膜之密封劑之框內整個面，立即貼合另一TAC膜。其後，使用金屬鹵素燈對密封劑部分照射100 mW/cm2 之紫外線30秒而獲得液晶顯示元件。 針對所獲得之液晶顯示元件，目視確認於在60℃、90%RH之環境下設為電壓施加狀態24小時後之密封劑附近之液晶配向混亂（顯示不均）。 將於液晶顯示元件完全觀察不到顯示不均之情形設為「○」，將於液晶顯示元件之密封劑附近（周邊部）觀察到顯示不均之情形設為「Δ」，將顯示不均不僅於周邊部，還擴展至中央部之情形設為「×」來評價低液晶污染性。 再者，評價為「○」之液晶顯示元件係實用上完全不存在問題之水準，「Δ」之液晶顯示元件係根據顯示設計而可能成為問題之水準，「×」之液晶顯示元件係不足以實用之水準。(Low liquid crystal contamination) 1 part by weight of spacer fine particles ("Micropearl SI-H050" manufactured by Sekisui Chemical Industry Co., Ltd.) was dispersed in 100 parts by weight of each sealant for liquid crystal display elements obtained in the examples and comparative examples. Next, a syringe for dispensing (manufactured by Musashi High-tech Co., Ltd., "PSY-10E") was filled with the sealant in which the spacer fine particles were dispersed, and degassing was performed. Use a dispenser (manufactured by Musashi High-tech Co., Ltd., "SHOTMASTER 300") to apply the degassed sealant to the two rubbed alignment films and the transparent TAC film with electrodes (Fuji) in such a way that the line width becomes 1 mm. One piece of "TD80UL" (produced by Film Film Company). Next, tiny droplets of liquid crystal (manufactured by Chisso Corporation, "JC-5004LA") are applied to the entire surface of the sealant frame of the TAC film, and another TAC film is immediately attached. Thereafter, a metal halide lamp was used to irradiate the sealant part with ultraviolet light of 100 mW/cm 2 for 30 seconds to obtain a liquid crystal display element. The obtained liquid crystal display element was visually confirmed to have disordered liquid crystal alignment (display unevenness) near the sealant after being placed in a voltage application state in an environment of 60° C. and 90% RH for 24 hours. The case where no display unevenness is observed on the liquid crystal display element is regarded as "○". The case where display unevenness is observed near the sealant (peripheral part) of the liquid crystal display element is regarded as "Δ". The case where display unevenness is observed is regarded as "Δ". Low liquid crystal contamination properties were evaluated as "×" when extending not only to the peripheral part but also to the central part. Furthermore, the liquid crystal display elements evaluated as "○" are at a level where there is no problem at all in practical use, the liquid crystal display elements with "Δ" are at a level that may cause problems depending on the display design, and the liquid crystal display elements with "×" are not sufficient. Practical level.
[表1]
[表2]
根據本發明，可提供一種對可撓性基板之接著性、防透濕性、及低液晶污染性優異之液晶顯示元件用密封劑。又，根據本發明，可提供一種使用該液晶顯示元件用密封劑而成之上下導通材料及液晶顯示元件。According to the present invention, it is possible to provide a sealant for liquid crystal display elements that is excellent in adhesion to a flexible substrate, moisture permeability prevention, and low liquid crystal contamination. Furthermore, according to the present invention, it is possible to provide an upper and lower conductive material and a liquid crystal display element using the sealant for liquid crystal display elements.
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| JP2003105207A (en) * | 2001-09-28 | 2003-04-09 | Chisso Corp | Resin composition and display device using the same |
| JP2006178053A (en) * | 2004-12-21 | 2006-07-06 | Dainippon Ink & Chem Inc | Photocurable composition for sealing liquid crystal panel, and liquid crystal panel |
| WO2013065828A1 (en) * | 2011-11-04 | 2013-05-10 | 積水化学工業株式会社 | Sealing agent for liquid crystal display element, vertically conducting material, and liquid crystal display element |
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| WO2001044342A1 (en) * | 1999-12-14 | 2001-06-21 | Mitsui Chemicals, Inc. | Sealing agent for liquid-crystal display cell, composition for sealing agent for liquid-crystal display cell, and liquid-crystal display element |
| JP2002069160A (en) * | 1999-12-14 | 2002-03-08 | Mitsui Chemicals Inc | Sealing agent for liquid crystal display cell, composition for sealing agent for liquid crystal display cell and liquid crystal display element |
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| JP2003105207A (en) * | 2001-09-28 | 2003-04-09 | Chisso Corp | Resin composition and display device using the same |
| JP2006178053A (en) * | 2004-12-21 | 2006-07-06 | Dainippon Ink & Chem Inc | Photocurable composition for sealing liquid crystal panel, and liquid crystal panel |
| WO2013065828A1 (en) * | 2011-11-04 | 2013-05-10 | 積水化学工業株式会社 | Sealing agent for liquid crystal display element, vertically conducting material, and liquid crystal display element |
| TW201510044A (en) * | 2013-05-23 | 2015-03-16 | Nippon Kayaku Kk | Resin composition for sealing organic el element, and cured product thereof |
| WO2017082000A1 (en) * | 2015-11-09 | 2017-05-18 | 積水化学工業株式会社 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
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