CN113924351B - Sealing agent for display element, vertically conductive material, and display element - Google Patents
Sealing agent for display element, vertically conductive material, and display element Download PDFInfo
- Publication number
- CN113924351B CN113924351B CN202080040561.8A CN202080040561A CN113924351B CN 113924351 B CN113924351 B CN 113924351B CN 202080040561 A CN202080040561 A CN 202080040561A CN 113924351 B CN113924351 B CN 113924351B
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- China
- Prior art keywords
- display element
- meth
- sealant
- acrylate
- compound
- Prior art date
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- 238000007789 sealing Methods 0.000 title claims abstract description 17
- 239000004020 conductor Substances 0.000 title claims description 9
- 239000000565 sealant Substances 0.000 claims abstract description 73
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 40
- 229920005989 resin Polymers 0.000 claims abstract description 29
- 239000011347 resin Substances 0.000 claims abstract description 29
- 230000009477 glass transition Effects 0.000 claims abstract description 19
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 19
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 12
- 238000012360 testing method Methods 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 102
- 239000004593 Epoxy Substances 0.000 claims description 88
- -1 methacryloyl group Chemical group 0.000 claims description 88
- 239000010419 fine particle Substances 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- 125000005641 methacryl group Chemical group 0.000 claims description 7
- 229910001507 metal halide Inorganic materials 0.000 claims description 4
- 150000005309 metal halides Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 abstract description 8
- 239000012298 atmosphere Substances 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 111
- 239000004973 liquid crystal related substance Substances 0.000 description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- 239000000126 substance Substances 0.000 description 20
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 18
- 239000010936 titanium Substances 0.000 description 18
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- 238000000034 method Methods 0.000 description 15
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 12
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- 239000007870 radical polymerization initiator Substances 0.000 description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
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- 229910000831 Steel Inorganic materials 0.000 description 6
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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
- 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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
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- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 2
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- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- 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
- UZDMJPAQQFSMMV-UHFFFAOYSA-N 4-oxo-4-(2-prop-2-enoyloxyethoxy)butanoic acid Chemical compound OC(=O)CCC(=O)OCCOC(=O)C=C UZDMJPAQQFSMMV-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
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- 239000002841 Lewis acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
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- 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
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241000204066 Tsukamurella Species 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
- 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
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- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 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
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 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
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 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
- 239000002981 blocking agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000005537 brownian motion Methods 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
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 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
- 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
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- 239000012954 diazonium Substances 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
- 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- 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
- 239000007789 gas Substances 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 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
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 150000007517 lewis acids Chemical class 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
- 125000005395 methacrylic acid group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 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
- 239000003605 opacifier Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 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
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011342 resin composition Substances 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
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000600 sorbitol Substances 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
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 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
- 238000002834 transmittance Methods 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-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
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Liquid Crystal (AREA)
- Sealing Material Composition (AREA)
- Electroluminescent Light Sources (AREA)
- Epoxy Resins (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
The purpose of the present invention is to provide a sealing agent for a display element, which can obtain a display element having excellent reliability in a high-temperature and high-humidity environment. The present invention also provides a vertical conduction material and a display element using the sealant for a display element. The sealant for display elements of the present invention contains a curable resin, a polymerization initiator and/or a thermosetting agent, and the cured product has a glass transition temperature of 125 ℃ or higher, and a cure shrinkage rate of 5% or less after a high-temperature high-humidity test in which the cured product is exposed to an atmosphere of 121 ℃, 100% RH, and 2atm for 48 hours.
Description
Technical Field
The present invention relates to a sealing agent for a display element, which can obtain a display element having excellent reliability in a high-temperature and high-humidity environment. The present invention also relates to a vertical conduction material and a display element using the sealant for a display element.
Background
In recent years, liquid crystal display elements, organic EL display elements, and the like have been widely used as display elements having characteristics of thin, light weight, low power consumption, and the like. In these display elements, sealing of liquid crystal, light-emitting layer, and the like is generally performed by using a sealant made of a curable resin composition.
For example, as a liquid crystal display element, a liquid crystal display element using a photo-thermal curing type sealant as disclosed in patent document 1 and patent document 2 is disclosed from the viewpoints of shortening the takt time and optimizing the amount of liquid crystal used.
In addition, as a display element, as a high reliability in driving under a high-temperature and high-humidity environment or the like, performance corresponding to a Pressure Cooker Test (PCT) under conditions of 121 ℃, 100% rh, 2atm is also required. In order to obtain a display element having high reliability, it is necessary to make the moisture and heat resistance of the sealant excellent.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2001-133794
Patent document 2: international publication No. 02/092718
Disclosure of Invention
Problems to be solved by the invention
The purpose of the present invention is to provide a sealing agent for a display element, which can obtain a display element having excellent reliability in a high-temperature and high-humidity environment. The present invention also provides a vertical conduction material and a display element using the sealant for a display element.
Means for solving the problems
The present invention provides a sealant for display elements, which contains a curable resin and a polymerization initiator and/or a thermosetting agent, wherein the glass transition temperature of the cured product is 125 ℃ or higher, and the cure shrinkage rate after a high-temperature high-humidity test in which the cured product is exposed to an atmosphere of 121 ℃, 100% RH, 2atm for 48 hours is 5% or less.
The present invention will be described in detail below.
The present inventors confirmed that there was a bubble intrusion in a display element, as a result of confirming that a display element which had failed to display when driving under a high temperature and high humidity environment. Accordingly, the present inventors studied to set the glass transition temperature of a cured product of a sealant for display elements to a specific value or higher and set the cure shrinkage of the cured product after exposure to high temperature and high humidity for 48 hours at 121 ℃, 100% rh, 2atm environment to a specific value or lower. As a result, it has been found that a sealant for a display element which can suppress the invasion of bubbles and can obtain a display element excellent in reliability in a high-temperature and high-humidity environment can be obtained, and the present invention has been completed.
The effect of the sealant for a display element of the present invention, which can provide a display element excellent in reliability under a high-temperature and high-humidity environment, is particularly remarkably exhibited when the sealant for a display element of the present invention is used as a sealant for a liquid crystal display element.
The lower limit of the glass transition temperature of the cured product of the sealant for display element of the present invention is 125 ℃. The sealing agent for display element obtained by setting the glass transition temperature of the cured product to 125 ℃ or higher and the cure shrinkage ratio to be described later to 5% or lower has an excellent effect of suppressing the invasion of bubbles in a high-temperature and high-humidity environment. The lower limit of the glass transition temperature of the cured product is preferably 130℃and more preferably 135 ℃.
In addition, from the viewpoint of adhesion, the upper limit of the glass transition temperature of the cured product is preferably 160 ℃.
In the present specification, the term "glass transition temperature" means: among the maxima of the loss tangent (tan δ) obtained by dynamic viscoelasticity measurement, a temperature of a maximum value due to micro-brownian motion appears. The glass transition temperature can be measured by a conventionally known method using a dynamic viscoelasticity measuring device or the like.
As a cured product for measuring the glass transition temperature, the following cured product was used: the sealant was irradiated with ultraviolet light (wavelength: 365 nm) of 100mW/cm 2 for 30 seconds using a metal halide lamp, and then heated at 120℃for 1 hour to cure the sealant, thereby obtaining a cured product.
In the sealant for display element of the present invention, the upper limit of the cure shrinkage after the high temperature and high humidity test of exposing the cured product to 121 ℃, 100% rh, and 2atm for 48 hours was 5%. The sealant for display element obtained by setting the cure shrinkage to 5% or less and the glass transition temperature of the cured product to 125 ℃ or more has excellent effect of suppressing the invasion of bubbles in a high-temperature and high-humidity environment. The upper limit of the curing shrinkage is preferably 4.8%, and more preferably 4.5%.
The preferable lower limit of the cure shrinkage is not particularly limited, but the substantial lower limit is 3%.
In the present specification, the "cure shrinkage" is a value calculated by the following formula when the ratio of the sealant for display element before curing at 25 ℃ is reset to G A and the ratio of the cured product after high temperature and high humidity test at 25 ℃ is reset to G B.
Cure shrinkage (%) = ((G B-GA)/GB) ×100
As a cured product to be subjected to the high temperature and high humidity test, a cured product was used, which was obtained by irradiating the sealant with ultraviolet light of 100mW/cm 2 for 30 seconds and then curing the sealant by heating at 120 ℃ for 1 hour.
The reason why the use of the sealant for a display element of the present invention can suppress the invasion of bubbles is considered as follows.
Namely, consider that: since the solidification shrinkage occurs in the high-temperature and high-humidity environment, a path for the moisture to penetrate into the solidified material is generated, and the moisture penetrating from the path becomes steam to generate bubbles. The cured product of the sealant for display element of the present invention has a glass transition temperature of 125 ℃ or higher and a cure shrinkage after the high temperature and high humidity test of 5% or less, and therefore it is presumed that the formation of such a path is suppressed.
In the sealant for a display element of the present invention, as a method for setting the glass transition temperature and the cure shrinkage of the cured product to the above ranges, a method for adjusting the types and the content ratios of the respective constituent components contained in the sealant for a display element is preferable.
As a method for setting the glass transition temperature of the cured product to the above range, for example, a curable resin having a hard skeleton such as bisphenol a skeleton, a polyfunctional curable resin for improving the crosslinking density, a methacryloyl ratio (METHACRYLIC RATIO) to be described later, and the like can be considered, but the method is not limited thereto. In addition, as a method for setting the cure shrinkage ratio to the above range, for example, a method of reducing the crosslinking density of the curable resin, a method of reducing the content ratio of the (meth) acryloyl group in the total of the (meth) acryloyl groups and the epoxy groups in the curable resin described later, and the like can be considered, but the method is not limited to these methods.
The sealant for display element of the present invention contains a curable resin.
The curable resin preferably contains a compound having a (meth) acryloyl group.
By containing the compound having a (meth) acryloyl group, the resulting sealant for a display element is excellent in low liquid crystal contamination property when used as a sealant for a liquid crystal display element. Among them, the curable resin preferably contains a compound having a methacryloyl group, in order to easily bring the glass transition temperature into the above range.
In the present specification, the "(meth) acryl" means acryl or methacryl.
When the curable resin contains the compound having a methacryloyl group, the methacryloyl ratio represented by the following formula (I) is preferably 0.5 or more. The above-mentioned glass transition temperature can be more easily brought into the above-mentioned range by setting the above-mentioned methacryloyl ratio to 0.5 or more. The ratio of methacryloyl groups is more preferably 0.6 or more.
Methacryloyl ratio= (W M/EM)/(WA/EA+WM/EM) (I)
In the formula (I), E A is an acryl equivalent (g/mol) of the compound having an acryl group, E M is a methacryl equivalent (g/mol) of the compound having a methacryl group, W A is a content (parts by weight) of the compound having an acryl group, and W M is a content (parts by weight) of the compound having a methacryl group.
The "acryl equivalent" is a value obtained by dividing the weight (g) of the compound having an acryl group by the number of moles (mol) of the acryl group contained in the compound having an acryl group. In the case where the curable resin contains a plurality of the compounds (A1, A2, & gtof) having an acryl group, the term "W A/EA" in the formula (I) means: for each compound having an acryl group, the sum of values obtained by dividing the content of the compound having an acryl group by the acryl equivalent (W A1/EA1+WA2/EA2 +). When the curable resin does not contain the compound having an acryl group, the "W A/EA" in the formula (I) is set to 0.
The "methacryloyl equivalent" is a value obtained by dividing the weight (g) of a compound having a methacryloyl group by the number of moles (mol) of the methacryloyl group contained in the compound having a methacryloyl group. In the case where the curable resin contains a plurality of the above-mentioned compounds (M1, M2, & ltCHEM & gt) having a methacryloyl group, "W M/EM" in the above formula (I) means: for each of the compounds having a methacryloyl group, the sum of the values obtained by dividing the content of the compound having a methacryloyl group by the equivalent amount of the methacryloyl group (W M1/EM1+WM2/EM2 +).
Examples of the compound having a (meth) acryloyl group include a partially (meth) acrylic-modified epoxy compound, an epoxy (meth) acrylate, a (meth) acrylate compound, and a urethane (meth) acrylate. Among them, the curable resin preferably contains a part of methacrylic acid-modified epoxy compound, more preferably contains a part of methacrylic acid-modified bisphenol a-type epoxy compound, in terms of making it easier to make the glass transition temperature and the cure shrinkage of the cured product in the above ranges, respectively.
In the present specification, the term "(meth) acrylic acid" refers to acrylic acid or methacrylic acid. The "partially (meth) acrylic-modified epoxy compound" is a compound obtained by reacting an epoxy group of a part of a compound having 2 or more epoxy groups with (meth) acrylic acid, and having 1 or more epoxy groups and (meth) acryloyl groups in each of 1 molecule. The term "(meth) acrylate" refers to an acrylate or a methacrylate, and the term "epoxy (meth) acrylate" refers to a compound obtained by reacting all of the epoxy groups in an epoxy compound with (meth) acrylic acid.
Examples of the epoxy compound that is a raw material for synthesizing the above-mentioned partially (meth) acrylic acid-modified epoxy compound include: bisphenol A type epoxy compound, bisphenol F type epoxy compound, bisphenol S type epoxy compound, 2' -diallyl bisphenol A type epoxy compound, hydrogenated bisphenol type epoxy compound, propylene oxide addition bisphenol A type epoxy compound, resorcinol type epoxy compound, biphenyl type epoxy compound, sulfide type epoxy compound, diphenyl ether type epoxy compound, dicyclopentadiene type epoxy compound, naphthalene type epoxy compound, phenol novolac type epoxy compound, o-cresol novolac type epoxy compound, dicyclopentadiene novolac type epoxy compound, biphenyl novolac type epoxy compound, naphthol novolac type epoxy compound, glycidylamine type epoxy compound, alkyl polyol type epoxy compound, rubber modified type epoxy compound, glycidyl ester compound, and the like.
Examples of commercial products of the bisphenol A type epoxy compound include jER828EL, jER1004 (both manufactured by Mitsubishi chemical corporation), EPICLON EXA-850CRP (manufactured by DIC corporation), and the like.
Examples of commercial products of the bisphenol F type epoxy compound include jER806 and jER4004 (both manufactured by Mitsubishi chemical corporation).
Examples of commercial products of the bisphenol S-type epoxy compound include EPICLON EXA and 1514 (available from DIC Co.).
Examples of the commercial products of the 2,2' -diallylbisphenol A type epoxy compound include RE-810NM (manufactured by Japanese chemical Co., ltd.).
Examples of commercial products of the hydrogenated bisphenol type epoxy compound include EPICLON EXA7015 (available from DIC corporation).
Examples of commercial products obtained by adding propylene oxide to bisphenol A type epoxy compounds include EP-4000S (manufactured by ADEKA).
Examples of commercial products of the resorcinol-type epoxy compound include EX-201 (manufactured by Nagase Chemtex Co., ltd.).
Examples of commercial products of the biphenyl epoxy compounds include jER YX-4000H (manufactured by mitsubishi chemical company).
Examples of the commercial products of the sulfide-type epoxy compounds include YSLV-50TE (NIPPON STEEL CHEMICAL, manufactured by Material Co.) and the like.
Examples of commercial products of the diphenyl ether type epoxy compounds include YSLV-80DE (NIPPON STEEL CHEMICAL & Material Co.) and the like.
Examples of commercial products of the dicyclopentadiene type epoxy compound include EP-4088S (manufactured by ADEKA Co., ltd.).
Examples of commercial products of the naphthalene type epoxy compound include EPICLON HP4032 and EPICLON EXA-4700 (all manufactured by DIC Co., ltd.).
As a commercially available product of the phenol novolac type epoxy compound, EPICLON N-770 (DIC Co.) and the like are exemplified.
As a commercially available product of the o-cresol novolac type epoxy compound, EPICLON N-670-EXP-S (DIC Co.) and the like are mentioned, for example.
Examples of the commercial products of the dicyclopentadiene phenol type epoxy compounds include EPICLON HP7200 (manufactured by DIC corporation).
Examples of commercial products of the biphenyl novolac type epoxy compounds include NC-3000P (manufactured by Japanese chemical Co., ltd.).
Examples of the commercial products of the naphthol novolac type epoxy compounds include ESN-165S (NIPPON STEEL CHEMICAL & Material Co.).
Examples of commercial products of the glycidylamine-type epoxy compounds include jER630 (manufactured by Mitsubishi chemical corporation), EPICLON 430 (manufactured by DIC corporation), TETRAD-X (manufactured by Mitsubishi gas chemical corporation), and the like.
Examples of commercial products of the alkyl polyol type epoxy compound include ZX-1542 (NIPPON STEEL CHEMICAL & Material Co., ltd.), EPICLON726 (DIC Co., ltd.), epoligo 80MFA (Co., ltd.), denacol EX-611 (Nagase Chemtex Co., ltd.), and the like.
Examples of commercial products of the rubber-modified epoxy compound include YR-450, YR-207 (both of which are manufactured by NIPPON STEEL CHEMICAL & Material Co., ltd.), and Epolead PB (manufactured by DAICEL Co., ltd.).
Examples of the commercial products of the above glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase Chemtex Co., ltd.).
Examples of other commercially available products of the epoxy compounds include YDC-1312, YSLV-80XY, YSLV-90CR (all of which are manufactured by NIPPON STEEL CHEMICAL & Material Co., ltd.), XAC4151 (manufactured by Asahi chemical Co., ltd.), jER1031, jER1032 (all of which are manufactured by Mitsubishi chemical Co., ltd.), EXA-7120 (manufactured by DIC Co., ltd.), TEPIC (manufactured by Nissan chemical Co., ltd.), and the like.
Examples of commercial products of the above-mentioned partially (meth) acrylic-modified epoxy compounds include UVACURE1561, KRM8287 (both manufactured by DAICEL ALLNEX), MEM-5000H (manufactured by NEO CHEMICAL).
Examples of the epoxy (meth) acrylate include: epoxy (meth) acrylate obtained by reacting an epoxy compound with (meth) acrylic acid in the presence of a basic catalyst according to a conventional method, and the like.
The epoxy compound used as a raw material for synthesizing the epoxy (meth) acrylate is the same epoxy compound as the epoxy compound used as a raw material for synthesizing the partially (meth) acrylic acid-modified epoxy compound.
Examples of the commercial products of the epoxy (meth) acrylates include epoxy (meth) acrylates manufactured by DAICEL ALLNEX, epoxy (meth) acrylates manufactured by new chemical industry, epoxy (meth) acrylates manufactured by co-mingled chemical industry, and epoxy (meth) acrylates manufactured by Nagase Chemtex.
Examples of the epoxy (meth) acrylate manufactured by DAICEL ALLNEX include EBECRYL860、EBECRYL3200、EBECRYL3201、EBECRYL3412、EBECRYL3600、EBECRYL3700、EBECRYL3701、EBECRYL3702、EBECRYL3703、EBECRYL3708、EBECRYL3800、EBECRYL6040、EBECRYL RDX63182.
Examples of the epoxy (meth) acrylate include EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, and EMA-1020.
Examples of the epoxy (meth) acrylate manufactured by the co-company chemical company include Epoxy Ester 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 Ester3000A、Epoxy Ester 200EA、Epoxy Ester 400EA.
Examples of the epoxy (meth) acrylate manufactured by Nagase Chemtex include Denacol ACRYLATE DA-141, denacol ACRYLATE DA-314, and Denacol ACRYLATE DA-911.
Examples of the monofunctional compound among the (meth) acrylate compounds include: methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, dicyclopentenyl (meth) acrylate, and process for the preparation of the same, tetrahydrofurfuryl (meth) acrylate, ethylcarbitol (meth) acrylate, 2-trifluoroethyl (meth) acrylate, 2, 3-tetrafluoropropyl (meth) acrylate, 1H, 5H-octafluoropentyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinate, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) acryloyloxyethyl phthalate, 2- (meth) acryloyloxyethyl phosphate, 2- (meth) acryloyloxyethyl glycidyl (meth) acrylate, and the like.
Examples of the 2-functional compound in the (meth) acrylate compound include: 1, 3-butanediol di (meth) acrylate, 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 di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, 2-n-butyl-2-ethyl-1, 3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide addition bisphenol a di (meth) acrylate, propylene oxide addition bisphenol a di (meth) acrylate, ethylene oxide addition bisphenol F di (meth) acrylate, dimethylol dicyclopentadiene di (meth) acrylate (japanese: a pair of late-pair and late-pair, wherein the late-pair is a pair of late-pair, and the late-pair is a pair of late-pair; ethylene oxide modified isocyanuric acid 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, polycaprolactone diol di (meth) acrylate, polybutadiene diol di (meth) acrylate, and the like.
Examples of the compound having 3 or more functions among the (meth) acrylate compounds include: trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide-added glycerol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tri (meth) acryloxyethyl phosphate, bis (trimethylolpropane) tetra (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.
The urethane (meth) acrylate may 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 compound.
Examples of the polyfunctional isocyanate compound include: isophorone diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4, 4' -diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1, 5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene Diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethylxylylene diisocyanate, 1,6, 11-undecane triisocyanate, and the like.
Further, as the above-mentioned polyfunctional isocyanate compound, a chain-extended polyfunctional isocyanate compound obtained by reacting a polyol with an excessive amount of the polyfunctional isocyanate compound may also be used.
Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate glycol, polyether glycol, polyester glycol, and polycaprolactone glycol.
Examples of the (meth) acrylic acid derivative having a hydroxyl group include hydroxyalkyl mono (meth) acrylate, mono (meth) acrylate of a diol, mono (meth) acrylate or di (meth) acrylate of a triol, and epoxy (meth) acrylate.
Examples of the hydroxyalkyl (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
Examples of the dihydric alcohol include ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 3-butanediol, 1, 4-butanediol, and polyethylene glycol.
Examples of the triol include trimethylolethane, trimethylolpropane, and glycerin.
Examples of the epoxy (meth) acrylate include bisphenol a type epoxy acrylate.
Examples of commercial products of the urethane (meth) acrylate include urethane (meth) acrylate produced by east asia synthesis company, urethane (meth) acrylate produced by DAICEL ALLNEX, urethane (meth) acrylate produced by the industry company in the new world, and urethane (meth) acrylate produced by the industry company in the co-ordination.
Examples of the urethane (meth) acrylate produced by the east Asia synthetic company include M-1100, M-1200, M-1210, and M-1600.
Examples of the urethane (meth) acrylate manufactured by DAICEL ALLNEX include EBECRYL210、EBECRYL220、EBECRYL230、EBECRYL270、EBECRYL1290、EBECRYL2220、EBECRYL4827、EBECRYL4842、EBECRYL4858、EBECRYL5129、EBECRYL6700、EBECRYL8402、EBECRYL8803、EBECRYL8804、EBECRYL8807、EBECRYL9260.
Examples of the urethane (meth) acrylate manufactured by the above-mentioned industrial company include ArtResin UN-330、ArtResin SH-500B、ArtResin UN-1200TPK、ArtResin UN-1255、ArtResin UN-3320HB、ArtResin UN-7100、ArtResin UN-9000A、ArtResin UN-9000H.
Examples of the urethane (meth) acrylate manufactured by the chemical industry company in the new country include U-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.
As urethane (meth) acrylate produced by the company of Cooperation, AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T and the like are mentioned, for example.
The curable resin may contain an epoxy compound for the purpose of improving the adhesiveness of the obtained sealant for element. Examples of the epoxy compound include the same epoxy compounds as those used as raw materials for synthesizing the partial (meth) acrylic acid modified epoxy compound.
When the curable resin contains the compound having a (meth) acryloyl group and the epoxy compound, the content of the (meth) acryloyl group in the total of the (meth) acryloyl groups and the epoxy groups in the curable resin is preferably 50 mol% or more and 95 mol% or less.
The sealant for display elements of the present invention contains a polymerization initiator and/or a thermosetting agent.
Examples of the polymerization initiator include a radical polymerization initiator and a cationic polymerization initiator.
Examples of the radical polymerization initiator include a photo radical polymerization initiator that generates radicals by irradiation with light, and a thermal radical polymerization initiator that generates radicals by heating.
Examples of the photo-radical polymerization initiator include benzophenone-based compounds, acetophenone-based compounds, acylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin ether-based compounds, and thioxanthone-based compounds.
Specific examples of the photo radical polymerization initiator include: 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, 2- (dimethylamino) -2- ((4-methylphenyl) methyl) -1- (4- (4-morpholino) phenyl) -1-butanone, 2-dimethoxy-1, 2-diphenylethan-1-one, bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1-one, 1- (4- (2-hydroxyethoxy) -phenyl) -2-hydroxy-2-methyl-1-propan-1-one, 1- (4- (phenylthio) phenyl) -1, 2-octadione 2- (O-benzoyloxime), 2,4, 6-trimethylbenzoyl diphenylphosphine oxide, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and the like.
Examples of the thermal radical polymerization initiator include thermal radical polymerization initiators composed of azo compounds, organic peroxides, and the like. Among them, a polymeric azo initiator composed of a polymeric azo compound is preferable.
In the present specification, the polymer azo compound means: a compound having an azo group and capable of generating a radical capable of curing a (meth) acryloyloxy group by heat, and having a number average molecular weight of 300 or more.
The number average molecular weight of the polymer azo compound is preferably 1000 at the lower limit and 30 tens of thousands at the upper limit. When the number average molecular weight of the polymer azo compound is in this range, the polymer azo compound can be easily mixed into the curable resin, and when the obtained sealant for a display element is used for a liquid crystal display element, adverse effects on liquid crystal can be prevented. The number average molecular weight of the polymer azo compound is more preferably limited to 5000, more preferably to 10 ten thousand, still more preferably to 1 ten thousand, and still more preferably to 9 ten thousand.
In the present specification, the number average molecular weight is a value obtained by measuring by Gel Permeation Chromatography (GPC) using tetrahydrofuran as a solvent and converting the obtained product into polystyrene. Examples of the column for measuring the number average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa electric company).
Examples of the polymer azo compound include: a polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via azo groups.
The polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via azo groups is preferably a polymer azo compound having a polyethylene oxide structure.
Specific examples of the polymer azo compound include a polycondensate of 4,4 '-azobis (4-cyanovaleric acid) and polyalkylene glycol, and a polycondensate of 4,4' -azobis (4-cyanovaleric acid) and polydimethylsiloxane having a terminal amino group.
Examples of commercial products of the polymer azo compound include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (both manufactured by Fuji photo-pure chemical Co., ltd.).
Examples of commercial products of the azo compound other than the polymer include V-65 and V-501 (both manufactured by Fuji photo-pure chemical Co., ltd.).
Examples of the organic peroxide include ketone peroxide, ketal peroxide, hydrogen peroxide, dialkyl peroxide, peroxyester, diacyl peroxide, and peroxydicarbonate.
As the cationic polymerization initiator, a photo-cationic polymerization initiator can be preferably used. The photo-cation polymerization initiator is not particularly limited as long as it generates a protonic acid or a lewis acid by irradiation with light, and may be an ionic photo-acid type photo-cation polymerization initiator or a nonionic photo-acid type photo-cation polymerization initiator.
Examples of the photo-cation polymerization initiator include onium salts such as aromatic diazonium salts, aromatic halonium salts and aromatic sulfonium salts, organometallic complexes such as iron-aromatic hydrocarbon complexes, titanocene complexes and arylsilanol-aluminum complexes.
Examples of commercial products of the photo-cation polymerization initiator include AdekaOptomer SP-150 and AdekaOptomer SP-170 (all manufactured by ADEKA).
The polymerization initiator may be used alone, or 2 or more kinds may be used in combination.
The preferable lower limit of the content of the polymerization initiator is 0.1 part by weight and the preferable upper limit is 30 parts by weight with respect to 100 parts by weight of the curable resin. The content of the polymerization initiator is 0.1 part by weight or more, whereby the obtained sealant for display element is more excellent in curability. The content of the polymerization initiator is 30 parts by weight or less, whereby the resulting sealant for display elements has more excellent storage stability. The more preferable lower limit of the content of the above-mentioned polymerization initiator is 1 part by weight, the more preferable upper limit is 10 parts by weight, and the more preferable upper limit is 5 parts by weight.
Examples of the thermosetting agent include organic acid hydrazides, imidazole derivatives, amine compounds, polyhydric phenol compounds, and acid anhydrides. Among them, solid organic acid hydrazides are preferably used.
The above-mentioned thermosetting agents may be used alone or in combination of 2 or more.
Examples of the solid organic acid hydrazide include 1, 3-bis (hydrazinocarbonylethyl) -5-isopropyl hydantoin, sebacic dihydrazide, isophthalic dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide, and the like.
Examples of the commercial products of the organic acid hydrazide include organic acid hydrazides manufactured by tsukamurella chemical company, organic acid hydrazides manufactured by Japan Finechem, and organic acid hydrazides manufactured by Ajinomoto Fine-Techno.
Examples of the organic acid hydrazide manufactured by tsukamurelchemical corporation include SDH and ADH.
Examples of the organic acid hydrazide manufactured by Japan Finechem include MDH.
Examples of the organic acid hydrazide manufactured by Ajinomoto Fine-Techno include AMICURE VDH, AMICURE VDH-J, and AMICURE UDH.
The content of the thermosetting agent is preferably 1 part by weight at a lower limit and 50 parts by weight at an upper limit, based on 100 parts by weight of the curable resin. When the content of the thermosetting agent is 1 part by weight or more, the obtained sealing agent for a display element is more excellent in thermosetting property. When the content of the thermosetting agent is 50 parts by weight or less, the obtained sealant for display element is more excellent in coatability and storage stability. The more preferable upper limit of the content of the above-mentioned thermosetting agent is 30 parts by weight.
The sealant for display element of the present invention preferably contains a filler for the purpose of viscosity adjustment, improvement of adhesion due to stress dispersion effect, improvement of linear expansion coefficient, improvement of moisture resistance of cured product, and the like.
As the filler, an inorganic filler and an organic filler can be used.
Examples of the inorganic filler include silica, talc, glass beads, asbestos, gypsum, diatomaceous earth, montmorillonite, bentonite, montmorillonite, sericite, activated clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, calcium carbonate, magnesium hydroxide, aluminum nitride, silicon nitride, barium sulfate, and calcium silicate.
Examples of the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles.
The preferable lower limit of the content of the filler in 100 parts by weight of the sealant for display element of the present invention is 10 parts by weight, and the preferable upper limit is 70 parts by weight. When the content of the filler is within this range, the effect of improving the adhesion and the like can be further exhibited while suppressing deterioration of the coating property and the like. The lower limit of the content of the filler is more preferably 20 parts by weight, and the upper limit is more preferably 60 parts by weight.
The sealing agent for display elements of the present invention preferably contains a silane coupling agent. The silane coupling agent mainly has a role as an adhesion promoter for favorably adhering the sealing agent to a substrate or the like.
As the silane coupling agent, for example, 3-mercaptopropyl trimethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-isocyanatopropyl trimethoxysilane, 3-glycidoxypropyl triethoxysilane, and the like are preferably used. These silane coupling agents have excellent effect of improving adhesion to a substrate or the like, and can suppress the outflow of a curable resin into a liquid crystal when the resulting sealant for a display element is used for a liquid crystal display element.
The silane coupling agent may be used alone or in combination of 2 or more.
The preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the sealant for display element of the present invention is 0.1 part by weight, and the preferable upper limit is 10 parts by weight. When the content of the silane coupling agent is within this range, the resulting sealant for a display element has more excellent adhesion, and when the resulting sealant for a display element is used for a liquid crystal display element, the occurrence of liquid crystal contamination can be suppressed. The more preferable lower limit of the content of the above silane coupling agent is 0.3 parts by weight, and the more preferable upper limit is 5 parts by weight.
The sealant for display element of the present invention may contain the above-mentioned light-shielding agent. By containing the above-described light-shielding agent, the sealant for a display element of the present invention can be suitably used as a light-shielding sealant.
Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Among them, titanium black is preferable.
The above-mentioned light-shielding agents may be used alone or in combination of 2 or more.
The titanium black is a substance having a higher transmittance for light in the vicinity of the ultraviolet region, particularly in the range of from 370nm to 450nm, than for light having a wavelength of from 300nm to 800 nm. That is, the titanium black is an opacifier having the following properties: the sealant for a display element of the present invention is provided with light shielding properties by sufficiently shielding light having a wavelength in the visible light range, and is transmitted by light having a wavelength in the vicinity of the ultraviolet range. The light-shielding agent contained in the sealant for display element of the present invention is preferably a material having high insulation properties, and titanium black is also suitable as the light-shielding agent having high insulation properties.
The titanium black exhibits sufficient effects even without surface treatment, but may be surface-treated titanium black such as titanium black surface-treated with an organic component such as a coupling agent, or titanium black surface-coated with an inorganic component such as silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide, magnesium oxide, or the like. Among them, titanium black treated with an organic component is preferable in that the insulation property can be further improved.
In addition, since the display element manufactured using the sealant for a display element of the present invention containing the titanium black as the light shielding agent has sufficient light shielding property, a display element having no light leakage, high contrast, and excellent image display quality can be realized.
Examples of the commercial products of the above titanium black include titanium black manufactured by Mitsubishi Materials, titanium black manufactured by red ear formation, and the like.
Examples of the titanium black manufactured by Mitsubishi Materials include 12S, 13M-C, 13R-N, and 14M-C.
Examples of the titanium black produced by the above-mentioned red spike chemical company include Tilack D.
The specific surface area of the titanium black is preferably limited to 13m 2/g at a lower limit, 30m 2/g at an upper limit, 15m 2/g at a lower limit, and 25m 2/g at an upper limit.
The preferable lower limit of the volume resistance of the titanium black is 0.5 Ω·cm, the preferable upper limit is 3 Ω·cm, the more preferable lower limit is 1 Ω·cm, and the more preferable upper limit is 2.5 Ω·cm.
The primary particle diameter of the light-shielding agent is not particularly limited as long as it is not more than the distance between the substrates of the display element, and is preferably 1nm as the lower limit and 5000nm as the upper limit. By setting the primary particle diameter of the light-shielding agent to this range, the light-shielding property can be further improved without deteriorating the drawing property and the like of the obtained sealing agent for display elements. The primary particle diameter of the light-shielding agent is more preferably 5nm in lower limit, more preferably 200nm in upper limit, still more preferably 10nm in lower limit, and still more preferably 100nm in upper limit.
The primary particle diameter of the light-shielding agent may be measured by dispersing the light-shielding agent in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (PARTICLE SIZING SYSTEMS).
The lower limit of the content of the light-shielding agent in 100 parts by weight of the sealant for display element of the present invention is preferably 5 parts by weight, and the upper limit is preferably 80 parts by weight. When the content of the light blocking agent is in this range, deterioration of adhesiveness, strength after curing, and drawing properties of the obtained sealant for display elements is suppressed, and the effect of improving light blocking properties is more excellent. The content of the light-shielding agent is more preferably 10 parts by weight, still more preferably 70 parts by weight, still more preferably 30 parts by weight, and still more preferably 60 parts by weight.
The sealant for display element of the present invention may further contain additives such as a reactive diluent, a spacer, a curing accelerator, an antifoaming agent, a leveling agent, a polymerization inhibitor, and other coupling agents, as necessary.
Examples of the method for producing the sealant for display elements of the present invention include a method in which a curable resin, a polymerization initiator and/or a thermosetting agent, and optionally a silane coupling agent are mixed using a mixer.
Examples of the mixer include a homodisperser, a homomixer, a universal mixer, a planetary mixer, a kneader, and a 3-roll machine.
By incorporating conductive fine particles into the sealing agent for display elements of the present invention, a vertically conductive material can be produced. Such a vertically conductive material containing the sealing agent for a display element and conductive fine particles of the present invention is also one of the present invention.
The conductive fine particles are not particularly limited, and metal spheres, fine particles having a conductive metal layer formed on the surface of the resin fine particles, and the like can be used. Among them, the fine particles having the conductive metal layer formed on the surface of the fine resin particles are preferable because the fine resin particles have excellent elasticity and can be electrically connected without damaging the transparent substrate or the like.
A display element having the cured product of the sealant for a display element of the present invention or the cured product of the vertically conductive material of the present invention is also one of the present invention. As the display element of the present invention, a liquid crystal display element is preferable.
As a method for manufacturing a liquid crystal display element using the sealant for a display element of the present invention, a liquid crystal dropping method is preferably used, and specifically, for example, a method having the following steps is exemplified.
First, the following steps are performed: the sealant for display element of the present invention is applied by screen printing, dispenser coating or the like to one of 2 transparent substrates having an electrode such as an ITO film, to form a frame-like seal pattern. Next, a step of applying droplets of liquid crystal dropwise to the entire inner surface of the frame of the seal pattern and stacking another transparent substrate under vacuum is performed. Then, a liquid crystal display element can be obtained by performing a step of temporarily curing the sealing agent by irradiating the sealing pattern portion with light such as ultraviolet light and a step of formally curing the temporarily cured sealing agent by heating.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, a sealant for a display element that can obtain a display element excellent in reliability in a high-temperature and high-humidity environment can be provided. Further, according to the present invention, it is possible to provide a vertically conductive material and a display element using the sealant for a display element.
Detailed Description
Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
Examples 1 to 5 and comparative examples 1 to 3
The materials were mixed using a planetary mixer according to the mixing ratio shown in table 1, and then mixed using a 3-roll machine, to prepare a sealant for display elements. As the above-mentioned planetary mixer, deaeration is performed using a tailang (manufactured by Thinky corporation).
The obtained sealant for display elements was irradiated with ultraviolet light (wavelength: 365 nm) of 100mW/cm 2 for 30 seconds using a metal halide lamp, and then heated at 120℃for 1 hour, whereby a cured product was obtained.
The obtained cured product was measured for dynamic viscoelasticity using a dynamic viscoelasticity measuring device under conditions of a test piece width of 5mm, a thickness of 0.35mm, a holding width of 25mm, a heating rate of 10 ℃/min, and a frequency of 5Hz, and the temperature at which the maximum value of loss tangent (tan. Delta.) was obtained was used as the glass transition temperature. As the dynamic viscoelasticity measuring apparatus, DVA-200 (manufactured by IT measurement control Co., ltd.) was used. The results are shown in Table 1.
The obtained cured product was subjected to a high temperature and high humidity test in which the cured product was exposed to an atmosphere of 121 ℃, 100% rh and 2atm for 48 hours. The specific gravity of the sealant for display element before curing at 25℃and the specific gravity of the cured product after high temperature and high humidity test at 25℃were measured, and the curing shrinkage was calculated from the above formula. The results are shown in Table 1.
< Evaluation >
The sealants for display elements obtained in examples and comparative examples were evaluated as follows. The results are shown in Table 1.
(Reliability in high-temperature and high-humidity Environment)
The spacer particles were uniformly dispersed in 100 parts by weight of each of the sealants for display elements obtained in examples and comparative examples. As the spacer, microPearl SI-H050 (manufactured by water chemical industry Co., ltd.) was used. The sealant containing the spacer dispersed therein was filled into a dispensing syringe, subjected to a defoaming treatment, and then applied to a transparent substrate with an alignment film and an ITO thin film by a dispenser so as to draw a rectangular frame. As a syringe, PSY-10E (manufactured by Musashi Engineering Co., ltd.) was used, and as a dispenser, SHOTMASTER300 (manufactured by Musashi Engineering Co., ltd.) was used. Next, minute droplets of liquid crystal were applied dropwise to the entire inner surface of the frame of the sealant, and another transparent substrate was immediately bonded. JC-5004LA (manufactured by CHISSO Co.) was used as the liquid crystal. Immediately after the transparent substrate was bonded, the sealant was irradiated with ultraviolet light (wavelength: 365 nm) of 100mW/cm 2 for 30 seconds using a metal halide lamp, and then heated at 120℃for 1 hour, whereby a liquid crystal display element was obtained. For each of the display element sealants obtained in examples and comparative examples, 20 liquid crystal display elements were produced.
The resulting liquid crystal display element was exposed to PCT conditions (121 ℃,100% rh,2 atm) for 48 hours. The presence or absence of bubbles was confirmed by visual observation of the liquid crystal display element after exposure to PCT conditions.
The case where no air bubbles were confirmed in each of 20 liquid crystal display elements was designated as "verygood", the case where air bubbles were confirmed in 1 or more and 3 or less liquid crystal display elements was designated as "good", the case where air bubbles were confirmed in 4 or more and 8 or less liquid crystal display elements was designated as "delta", the case where air bubbles were confirmed in 9 or more liquid crystal display elements was designated as "×", and reliability under high temperature and high humidity environment was evaluated.
TABLE 1
Industrial applicability
According to the present invention, a sealant for a display element that can obtain a display element excellent in reliability in a high-temperature and high-humidity environment can be provided. Further, according to the present invention, it is possible to provide a vertically conductive material and a display element using the sealant for a display element.
Claims (4)
1. A sealing agent for display elements, characterized by comprising a curable resin, a polymerization initiator and a thermosetting agent,
The sealant for display element was irradiated with ultraviolet light having a wavelength of 365nm and 100mW/cm 2 for 30 seconds using a metal halide lamp, and then heated at 120℃for 1 hour to cure the sealant, whereby the glass transition temperature of the cured product was 125℃or higher,
The sealant for display element is irradiated with ultraviolet rays of 100mW/cm 2 for 30 seconds, and then heated at 120 ℃ for 1 hour to cure the sealant to obtain a cured product, the cured product is exposed to high temperature and high humidity test for 48 hours at 121 ℃, 100% RH and 2atm for a period of time, the cure shrinkage rate is not more than 5%,
The curable resin contains a compound having a methacryloyl group,
The ratio of methacryloyl groups represented by the following formula (I) is 0.5 or more,
Methacryloyl ratio= (W M/EM)/(WA/EA+WM/EM) (I)
In the formula (I), E A is an acryl equivalent of the compound having an acryl group, E M is a methacryl equivalent of the compound having a methacryl group, W A is a content of the compound having an acryl group, W M is a content of the compound having a methacryl group, units of E A and E M are g/mol, units of W A and W M are parts by weight,
The compound having a methacryloyl group is a partially methacrylic acid modified epoxy compound.
2. The sealant for a display element according to claim 1, wherein the curable resin contains a part of methacrylic acid-modified bisphenol a type epoxy compound.
3. A vertically conductive material comprising the sealant for a display element according to claim 1 or 2 and conductive fine particles.
4. A display element having the cured product of the sealant for a display element according to claim 1 or 2 or the cured product of the vertically conductive material according to claim 3.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2019-123019 | 2019-07-01 | ||
| JP2019123019 | 2019-07-01 | ||
| JP2019-126948 | 2019-07-08 | ||
| JP2019126948 | 2019-07-08 | ||
| PCT/JP2020/025479 WO2021002317A1 (en) | 2019-07-01 | 2020-06-29 | Sealing agent for display elements, vertically conductive material, and display element |
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| CN113924351A CN113924351A (en) | 2022-01-11 |
| CN113924351B true CN113924351B (en) | 2024-09-03 |
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| CN202080036217.1A Active CN113826043B (en) | 2019-07-01 | 2020-06-29 | Sealing agent for display element, vertically conductive material, and display element |
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| KR (2) | KR102719152B1 (en) |
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| JP7421691B1 (en) | 2022-03-25 | 2024-01-24 | 積水化学工業株式会社 | Sealant for liquid crystal display elements and liquid crystal display elements |
| WO2024014379A1 (en) * | 2022-07-12 | 2024-01-18 | ソニーセミコンダクタソリューションズ株式会社 | Light-emitting device, electronic apparatus, and sealing device |
| WO2024065048A1 (en) * | 2022-09-27 | 2024-04-04 | Zeroin Foods Inc. | Sweetened fiber and methods thereof |
| WO2024225246A1 (en) * | 2023-04-24 | 2024-10-31 | 積水化学工業株式会社 | Curable resin composition, coating layer, and film |
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| JP2000066220A (en) * | 1998-08-19 | 2000-03-03 | Sumitomo Bakelite Co Ltd | Sealing material for liquid crystal display element and liquid crystal display element using the material |
| JP2000227600A (en) * | 1998-11-30 | 2000-08-15 | Toshiba Corp | Manufacture of liquid crystal display cell |
| 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 |
| 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 |
| 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 |
| JP2002317172A (en) * | 2001-04-20 | 2002-10-31 | Nippon Kayaku Co Ltd | Sealing medium resin composition for liquid crystal display |
| JP3795459B2 (en) | 2001-05-16 | 2006-07-12 | 積水化学工業株式会社 | Curable resin composition, display element sealing agent and display element sealing agent |
| JP2009134293A (en) * | 2007-11-08 | 2009-06-18 | Sekisui Chem Co Ltd | Sealing agent for liquid crystal installation method, vertical conduction material and liquid crystal display element |
| JP2009155589A (en) * | 2007-12-28 | 2009-07-16 | Three Bond Co Ltd | Curable composition |
| TWI569096B (en) * | 2011-08-10 | 2017-02-01 | 東亞合成股份有限公司 | Active energy ray-curable film for gap filling and a preparation method thereof |
| WO2013191169A1 (en) * | 2012-06-20 | 2013-12-27 | 三菱レイヨン株式会社 | Method for producing laminate, laminate, and article |
| CN102888199B (en) * | 2012-09-17 | 2014-06-18 | 北京京东方光电科技有限公司 | Frame sealing glue and preparation method and application thereof |
| JP6159191B2 (en) * | 2013-08-07 | 2017-07-05 | 積水化学工業株式会社 | Liquid crystal dropping method sealing agent, vertical conduction material, and liquid crystal display element |
| JP6491542B2 (en) * | 2014-06-03 | 2019-03-27 | 積水化学工業株式会社 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
| JP6431422B2 (en) * | 2015-03-27 | 2018-11-28 | 株式会社ジャパンディスプレイ | Liquid crystal display |
| KR101939035B1 (en) * | 2015-11-09 | 2019-01-15 | 세키스이가가쿠 고교가부시키가이샤 | Sealant for liquid crystal display element, vertical conduction material, and liquid crystal display element |
| JP7388808B2 (en) * | 2017-09-19 | 2023-11-29 | 共栄社化学株式会社 | Method for producing partially esterified epoxy resin |
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| CN106796376A (en) * | 2015-05-08 | 2017-05-31 | 积水化学工业株式会社 | Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display cells |
| CN108780251A (en) * | 2016-09-29 | 2018-11-09 | 积水化学工业株式会社 | Sealing material for liquid crystal display device, upper and lower conductive material and liquid crystal display element |
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| JP6905158B2 (en) | 2021-07-21 |
| CN113826043B (en) | 2024-07-23 |
| CN113924351A (en) | 2022-01-11 |
| TW202108694A (en) | 2021-03-01 |
| TWI849163B (en) | 2024-07-21 |
| WO2021002318A1 (en) | 2021-01-07 |
| KR102719152B1 (en) | 2024-10-17 |
| CN113826043A (en) | 2021-12-21 |
| JPWO2021002318A1 (en) | 2021-09-13 |
| JP6910561B2 (en) | 2021-07-28 |
| WO2021002317A1 (en) | 2021-01-07 |
| KR20220023751A (en) | 2022-03-02 |
| JP2021167416A (en) | 2021-10-21 |
| KR20220027054A (en) | 2022-03-07 |
| JPWO2021002317A1 (en) | 2021-09-13 |
| JP2021177246A (en) | 2021-11-11 |
| TW202108693A (en) | 2021-03-01 |
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