WO2013035723A1 - Adhesive for bonding front plate for display devices, adhesive set for bonding front plate for display devices, method for manufacturing display device, and display device - Google Patents
Adhesive for bonding front plate for display devices, adhesive set for bonding front plate for display devices, method for manufacturing display device, and display device Download PDFInfo
- Publication number
- WO2013035723A1 WO2013035723A1 PCT/JP2012/072565 JP2012072565W WO2013035723A1 WO 2013035723 A1 WO2013035723 A1 WO 2013035723A1 JP 2012072565 W JP2012072565 W JP 2012072565W WO 2013035723 A1 WO2013035723 A1 WO 2013035723A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- front plate
- display device
- agent
- adhesive
- bonding
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 143
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 138
- 238000004519 manufacturing process Methods 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 229920001519 homopolymer Polymers 0.000 claims abstract description 75
- 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 241
- 239000000463 material Substances 0.000 claims description 62
- 239000007870 radical polymerization initiator Substances 0.000 claims description 28
- 230000001678 irradiating effect Effects 0.000 claims description 21
- 238000010030 laminating Methods 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 9
- 230000002093 peripheral effect Effects 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical group CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003999 initiator Substances 0.000 abstract description 7
- IAMASUILMZETHW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCC(O)OC1=CC=CC=C1 IAMASUILMZETHW-UHFFFAOYSA-N 0.000 description 47
- 239000002585 base Substances 0.000 description 45
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- 238000000576 coating method Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
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- 239000004973 liquid crystal related substance Substances 0.000 description 12
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- 238000002834 transmittance Methods 0.000 description 7
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- SAJYOGBRPOXCIN-UHFFFAOYSA-N 1-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-2-phenylundecan-2-ol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCOCCOCCOCC(O)(CCCCCCCCC)C1=CC=CC=C1 SAJYOGBRPOXCIN-UHFFFAOYSA-N 0.000 description 5
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 5
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
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- 239000004593 Epoxy Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
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- 239000002390 adhesive tape Substances 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 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 3
- 238000006243 chemical reaction Methods 0.000 description 3
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- RSVDRWTUCMTKBV-UHFFFAOYSA-N sbb057044 Chemical compound C12CC=CC2C2CC(OCCOC(=O)C=C)C1C2 RSVDRWTUCMTKBV-UHFFFAOYSA-N 0.000 description 3
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- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- COORVRSSRBIIFJ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]-1-methoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(O)COCCOCCO COORVRSSRBIIFJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
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- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 239000011347 resin Substances 0.000 description 2
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- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
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- VETIYACESIPJSO-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOC(=O)C=C VETIYACESIPJSO-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
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- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
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- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
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- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 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
- 239000004927 clay Substances 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
- 238000013016 damping Methods 0.000 description 1
- ZOJPTQRKWVDKTP-UHFFFAOYSA-N decane methanol prop-2-enoic acid Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.CO.CO.CCCCCCCCCC ZOJPTQRKWVDKTP-UHFFFAOYSA-N 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000004386 diacrylate group Chemical group 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
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical group C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- UOMUPDCRXJLVGR-UHFFFAOYSA-N propane-1,2,2-triol Chemical group CC(O)(O)CO UOMUPDCRXJLVGR-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/87—Passivation; Containers; Encapsulations
- H10K59/871—Self-supporting sealing arrangements
- H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/88—Dummy elements, i.e. elements having non-functional features
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
- H10K71/421—Thermal treatment, e.g. annealing in the presence of a solvent vapour using coherent electromagnetic radiation, e.g. laser annealing
Definitions
- the present invention is excellent in transparency and moisture resistance of a cured product, and can sufficiently bond the front plate and the base material even when the polarity of the front plate and the base material on which the front plate is bonded is greatly different.
- the present invention relates to an adhesive for bonding a front plate for a display device.
- the present invention also relates to a display device using the display device front plate bonding adhesive and a method for manufacturing the display device.
- a touch panel or a 3D display function is provided on a flat panel display such as a liquid crystal display, a plasma display, and an organic EL display are widely used.
- This display device is manufactured by bonding a front panel such as a protective panel, an antireflection panel, a touch panel, a 3D display lens sheet, and a barrier liquid crystal panel to a base material.
- Patent Documents 1 and 2 disclose coating-type adhesives that replace adhesive tapes.
- the adhesive disclosed in Patent Document 1 is composed of a hydrophobic material mainly composed of synthetic rubber, there is a problem that the affinity with a hydrophilic base material such as glass is not good.
- the adhesive disclosed in Patent Document 2 has a problem that the front plate and the base material cannot be sufficiently bonded.
- Patent Document 3 discloses a resin composition containing an alkyl acrylate and an acrylate having a hydroxyl group.
- the resin composition disclosed in Patent Document 3 is a mixture of resins having different polarities, there is a problem in compatibility, and the cured product is exposed to light, particularly when exposed to a high humidity environment. There was a problem that it was easily clouded.
- the conventional adhesive has a problem that the front plate may be peeled off due to poor adhesion when the polarity of the front plate and the substrate to which the front plate is bonded is greatly different.
- JP 2005-015598 A Japanese Patent Laid-Open No. 7-134212 Japanese Patent Laid-Open No. 9-258023
- the present invention is excellent in transparency and moisture resistance of a cured product, and can sufficiently bond the front plate and the base material even when the polarity of the front plate and the base material on which the front plate is bonded is greatly different.
- An object of the present invention is to provide an adhesive for bonding a front plate for a display device.
- Another object of the present invention is to provide a display device using the adhesive for bonding a front plate for a display device.
- the present invention is an adhesive used for bonding a substrate of a display device to a front plate, a monofunctional radical polymerizable compound having a hydrophilic group and a hydrophobic group in the molecule, and the monofunctional radical polymerizable compound
- the inventors use a monofunctional radical polymerizable compound having a hydrophilic group and a hydrophobic group in the molecule, a homopolymer of the monofunctional radical polymerizable compound, and a polyfunctional radical polymerizable compound in combination.
- the display is excellent in transparency and moisture resistance of the cured product, and can sufficiently bond the front plate and the base material even when the polarity of the front plate and the base material to which the front plate is bonded is greatly different. It has been found that an adhesive for bonding a front plate for a device can be obtained, and the present invention has been completed.
- the adhesive for bonding a front plate for a display device of the present invention contains a monofunctional radical polymerizable compound having a hydrophilic group and a hydrophobic group in the molecule (hereinafter also simply referred to as a monofunctional radical polymerizable compound).
- a monofunctional radical polymerizable compound By using a monofunctional compound as the radical polymerizable compound, a homopolymer having high compatibility with the radical polymerizable compound can be obtained without gelation.
- the monofunctional radically polymerizable compound has a hydrophilic group and a hydrophobic group in the molecule, the front plate to be bonded and the base material are sufficiently different even if the front plate and the base material are made of materials having significantly different polarities. Can be glued.
- it since it has a hydrophilic group, it can suppress that a hardened
- hydrophilic group examples include (poly) ethylene glycol group, (poly) propylene glycol group, (poly) tetramethylene glycol group, (poly) 2-hydroxypropylene glycol group and the like.
- (poly) ethylene glycol groups are preferred because they are highly hydrophilic and the resulting adhesive is excellent in adhesion to highly polar substrates.
- hydrophobic group examples include a phenyl group, an alkyl group, an alkylphenyl group, an isobornyl group, a tricyclodecane dimethanol group, and the like. Of these, a phenyl group is preferred because of its good affinity with the resin.
- the monofunctional radically polymerizable compound having a hydrophilic group and a hydrophobic group in the molecule include phenoxydiethylene glycol acrylate, 2-ethylhexyl diethylene glycol acrylate, and nonylphenoxy diethylene glycol acrylate.
- the adhesive agent for front plate bonding for display devices obtained becomes the thing excellent in adhesiveness with a base material, the compound represented by following formula (1) is suitable.
- R 1 represents hydrogen or a methyl group
- R 2 represents a linear or branched saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms or a 2-hydroxypropylene group
- R 3 represents a substituent represented by the following formula (2-1), (2-2), (2-3), or (2-4), and n is an integer of 1 to 6 Indicates.
- R 4 represents hydrogen or a linear or branched alkyl group having 1 to 12 carbon atoms.
- R 2 may be a linear or branched saturated aliphatic hydrocarbon group having 1 to 6 carbon atoms, but is preferably a methylene group, an ethylene group or a propylene group.
- Examples of the monofunctional radically polymerizable compound having a substituent represented by the formula (2-1) include phenoxyethyl acrylate (manufactured by Kyoeisha Chemical Co., “Light Acrylate PO-A”, Daicel Cytec Co., Ltd., “EBECRYL110”).
- Phenyldiethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “light acrylate P-200A”), nonylphenol EO adduct acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “light acrylate NP-4EA”), 2-hydroxy-3-phenoxypropyl acrylate ( And “Epoxy ester M-600A” manufactured by Kyoeisha Chemical Co., Ltd.).
- Examples of the monofunctional radically polymerizable compound having a substituent represented by the formula (2-2) include dicyclopentenyloxyethyl acrylate (manufactured by Hitachi Chemical Co., Ltd., “Fancryl FA-512AS”).
- a preferable upper limit is 0.5 mgKOH / g.
- the upper limit with the more preferable acid value of the said monofunctional radically polymerizable compound is 0.1 mgKOH / g.
- the content of the monofunctional radical polymerizable compound is not particularly limited, but the total amount of the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, and the polyfunctional radical polymerizable compound is 100 parts by weight.
- the preferred lower limit is 5 parts by weight and the preferred upper limit is 90 parts by weight.
- the content of the monofunctional radically polymerizable compound is less than 5 parts by weight, the viscosity of the obtained adhesive for bonding a front plate for a display device becomes too high, and coating may be difficult.
- the resulting adhesive for bonding a front plate for a display device is bonded to the front plate and the substrate, resulting in large shrinkage and deformation. Or the viscosity may be too low.
- the minimum with more preferable content of the said monofunctional radically polymerizable compound is 10 weight part, and a more preferable upper limit is 80 weight part.
- the adhesive for bonding a front plate for a display device of the present invention contains a homopolymer of the above monofunctional radically polymerizable compound.
- a homopolymer of the above-mentioned monofunctional radical polymerizable compound as a polymer to be blended in order to reduce cure shrinkage, improve adhesion and dimensional stability, or adjust viscosity, the cured product after light irradiation Can be suppressed from becoming cloudy.
- the upper limit with preferable glass transition temperature of the homopolymer of the said monofunctional radically polymerizable compound is 25 degreeC.
- the glass transition temperature of the homopolymer of the monofunctional radical polymerizable compound exceeds 25 ° C., the obtained display device may be inferior in impact resistance.
- the preferable lower limit of the weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC) of the homopolymer of the monofunctional radical polymerizable compound is 3000, and the preferable upper limit is 200,000.
- GPC gel permeation chromatography
- the weight average molecular weight of the homopolymer of the monofunctional radically polymerizable compound exceeds 200,000, the viscosity of the obtained adhesive for bonding a front plate for a display device becomes too high, and coating may be difficult.
- the minimum with a more preferable weight average molecular weight of the homopolymer of the said monofunctional radically polymerizable compound is 20,000, and a more preferable upper limit is 80,000.
- An example of a column for measuring the weight average molecular weight in terms of polystyrene by GPC is LF-804 (manufactured by SHOKO).
- the homopolymer content of the monofunctional radical polymerizable compound is not particularly limited, but a total of 100 of the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, and the polyfunctional radical polymerizable compound is 100.
- the preferred lower limit is 10 parts by weight and the preferred upper limit is 80 parts by weight with respect to parts by weight.
- the content of the homopolymer of the monofunctional radical polymerizable compound is less than 10 parts by weight, the curing shrinkage is large, and the obtained adhesive for bonding the front plate for a display device is a substrate on which the front plate or the front plate is bonded. It may become inferior in adhesiveness, may be deformed, or may have insufficient viscosity.
- the content of the homopolymer of the monofunctional radically polymerizable compound exceeds 80 parts by weight, the viscosity of the obtained adhesive for bonding a front plate for a display device becomes too high, and coating may be difficult.
- the minimum with more preferable content of the homopolymer of the said monofunctional radically polymerizable compound is 20 weight part, and a more preferable upper limit is 70 weight part.
- the adhesive for bonding a front plate for a display device of the present invention contains a polyfunctional radically polymerizable compound.
- the adhesive agent for front plate bonding for display devices of this invention becomes a crosslinked body after hardening, and a shape maintenance is possible also at high temperature.
- polyfunctional radical polymerizable compound examples include polyfunctional epoxy acrylates such as bisphenol A diglycidyl ether diacrylate and polyethylene glycol diglycidyl ether diacrylate, trimethylolpropane triacrylate, tetramethylolmethane tetraacrylate, and pentaerythritol triacrylate.
- polyfunctional epoxy acrylates such as bisphenol A diglycidyl ether diacrylate and polyethylene glycol diglycidyl ether diacrylate, trimethylolpropane triacrylate, tetramethylolmethane tetraacrylate, and pentaerythritol triacrylate.
- the content of the polyfunctional radical polymerizable compound is not particularly limited, but the total amount of the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, and the polyfunctional radical polymerizable compound is 100 parts by weight.
- the preferred lower limit is 1 part by weight and the preferred upper limit is 30 parts by weight. If the content of the polyfunctional radically polymerizable compound is less than 1 part by weight, crosslinking may be insufficient and deviation may occur at high temperatures. If the content of the polyfunctional radically polymerizable compound exceeds 30 parts by weight, it may become too hard and the impact resistance may be lowered.
- the minimum with more preferable content of the said polyfunctional radically polymerizable compound is 5 weight part, and a more preferable upper limit is 20 weight part.
- the adhesive for bonding a front plate for a display device of the present invention contains a radical photopolymerization initiator.
- the radical photopolymerization initiator is not particularly limited, and examples thereof include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, and thioxanthone.
- photo radical polymerization initiators examples include Irgacure 184, Irgacure 369, Irgacure 379, Irgacure 651, Irgacure 819, Irgacure 907, Irgacure 2959, Irgacure OXE01, and Lucyrin TPO (all of which are BASF Japan).
- Benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether all of which are manufactured by Tokyo Chemical Industry Co., Ltd.
- Irgacure 651, Irgacure 907, benzoin isopropyl ether, and Lucillin TPO are preferable because of their wide absorption wavelength range.
- These radical photopolymerization initiators may be used alone or in combination of two or more.
- the content of the photo radical polymerization initiator is not particularly limited, but is 100 parts by weight in total of the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, and the polyfunctional radical polymerizable compound.
- the preferred lower limit is 0.5 parts by weight, and the preferred upper limit is 10 parts by weight.
- the content of the photo radical polymerization initiator is less than 0.5 parts by weight, the polymerization does not proceed sufficiently, or the curing reaction of the obtained adhesive for bonding the front plate for a display device is too slow. Sometimes.
- the curing reaction of the obtained adhesive for bonding a front plate for a display device becomes too fast, resulting in a decrease in workability or an obtained display device.
- the adhesive for bonding the front plate may become a non-uniform cured product.
- the minimum with more preferable content of the said radical photopolymerization initiator is 1 weight part, and a more preferable upper limit is 5 weight part.
- the adhesive for bonding a front plate for a display device of the present invention preferably contains a thermal radical polymerization initiator.
- Any thermal radical polymerization initiator may be used as long as it decomposes at a temperature of 100 ° C. or lower to generate radicals, and is selected in consideration of the film forming temperature, the crosslinking temperature, the storage stability, and the like. Can be used. Among these, those having a decomposition temperature of 70 ° C. or less with a half-life of 10 hours are preferably used because of low temperature curability.
- the thermal radical polymerization initiator include azo compounds and organic peroxides. Of these, organic peroxides are preferable.
- organic peroxide examples include 2,5-dimethylhexane-2,5-dihydroxyperoxide, 2,5-dimethyl-2,5-di (t-butylperoxy) hexyne-3, di- t-butyl peroxide, t-butylcumyl peroxide, 2,5-dimethyl-2,5-di (t-butylperoxy) hexane, dicumyl peroxide, ⁇ , ⁇ '-bis (t-butylperoxy) Isopropyl) benzene, n-butyl-4,4-bis- (t-butylperoxy) valerate, 2,2-bis (t-butylperoxy) butane, 1,1-bis (t-butylperoxy) cyclohexane 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, t-butylperoxybenzoate, benzoyl peroxide
- the content of the thermal radical polymerization initiator is not particularly limited, but with respect to a total of 100 parts by weight of the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, and the polyfunctional radical polymerizable compound.
- the preferred lower limit is 0.1 parts by weight, and the preferred upper limit is 10 parts by weight.
- the content of the thermal radical polymerization initiator is less than 0.1 parts by weight, the polymerization does not proceed sufficiently, or the curing reaction of the obtained adhesive for bonding a front plate for a display device is too slow. Sometimes.
- the content of the thermal radical polymerization initiator exceeds 10 parts by weight, foaming may occur at the time of curing, or the storage stability of the obtained adhesive for bonding a front plate for a display device may be poor and the viscosity may increase. is there.
- the minimum with more preferable content of the said thermal radical polymerization initiator is 1 weight part.
- the adhesive for bonding a front plate for a display device of the present invention may contain a silane coupling agent as an adhesion promoter as long as the object of the present invention is not impaired.
- a silane coupling agent include vinyltriethoxysilane, vinyltris ( ⁇ -methoxyethoxy) silane, ⁇ -methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, and ⁇ -glycidoxypropyltrimethoxy.
- silane ⁇ -glycidoxypropyltriethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ -chloropropylmethoxysilane, vinyltrichlorosilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyl And triethoxysilane, N- ⁇ (aminoethyl) - ⁇ -aminopropyltrimethoxysilane, and the like.
- silane coupling agents may be used alone or in combination of two or more.
- the content of the silane coupling agent is not particularly limited, but is 100 parts by weight in total of the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, and the polyfunctional radical polymerizable compound.
- the preferred lower limit is 0.01 parts by weight and the preferred upper limit is 5 parts by weight.
- content of the silane coupling agent is less than 0.01 part by weight, the effect of improving the adhesiveness of the obtained adhesive for bonding a front plate for a display device may not be sufficiently obtained.
- content of the said silane coupling agent exceeds 5 weight part, an excess silane coupling agent may bleed out.
- the minimum with more preferable content of the said silane coupling agent is 0.5 weight part.
- the adhesive for bonding a front plate for a display device of the present invention may contain a filler as long as the object of the present invention is not impaired.
- the said filler is not specifically limited, For example, an inorganic filler, an organic filler, etc. are mentioned.
- the inorganic filler is not particularly limited. For example, talc, silica, smectite, bentonite, calcium carbonate, magnesium carbonate, alumina, montmorillonite, diatomaceous earth, magnesium oxide, titanium oxide, magnesium hydroxide, aluminum hydroxide, glass beads, barium sulfate. , Gypsum, calcium silicate, sericite activated clay and the like.
- the organic filler is not particularly limited, and examples thereof include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles. These fillers may be used independently and may use 2 or more types together.
- the method for producing the adhesive for bonding a front plate for a display device of the present invention is not particularly limited.
- the monofunctional radical polymerizable compound, a homopolymer of the monofunctional radical polymerizable compound, the polyfunctional radical polymerizable compound, the photo radical polymerization initiator, the thermal radical polymerization initiator, and the silane coupling agent The method of mixing with additives, such as these, is mentioned.
- the viscosity of the adhesive for bonding a front plate for a display device of the present invention is not particularly limited, but a preferable lower limit of the viscosity measured at 25 ° C. and 2.5 rpm using an E-type viscometer is preferably 20 mPa ⁇ s.
- the upper limit is 500,000 mPa ⁇ s.
- the viscosity is less than 20 mPa ⁇ s, the adhesive for bonding a front plate for a display device may flow out during coating.
- the viscosity of the adhesive for laminating a front plate for a display device exceeds 500,000 mPa ⁇ s, coating may be difficult.
- the more preferable lower limit of the viscosity of the adhesive for bonding a front plate for a display device is 50 mPa ⁇ s, and the more preferable upper limit is 200,000 mPa ⁇ s.
- a method for manufacturing a display device is also one aspect of the present invention.
- the display device front plate bonding adhesive of the present invention is applied to the front plate.
- it may be applied to a base material to which the front plate is bonded.
- the thickness of the pressure-sensitive adhesive layer by the adhesive for bonding a front plate for a display device of the present invention after coating is appropriately determined depending on the material, application, etc., but is usually about 1 to 200 ⁇ m.
- the front plate examples include a protective panel made of glass, polycarbonate, acrylic, or the like, a resistive or capacitive touch panel, a lenticular lens for 3D display, a barrier liquid crystal panel called a parallax barrier, and the like.
- the substrate on which the front plate is bonded examples include a liquid crystal panel module, an organic EL panel module, a plasma display, and electronic paper.
- the front plate bonding adhesive for display devices of the present invention can also be used for bonding different front plates.
- the method for applying the adhesive for bonding a front plate for a display device of the present invention is not particularly limited, and for example, it can be performed using a coating machine such as a roll coater or a die coater. In particular, in order to apply uniformly, it is preferable to apply to the substrate while heating with a die coater or the like.
- the front plate bonding adhesive for display device of the present invention is After the coating, it can be cured by irradiating with light having a wavelength of 300 nm to 400 nm and an integrated light amount of 300 to 3000 mJ / cm 2 .
- the light source for irradiating the light for curing the adhesive for bonding the front plate for display device of the present invention is not particularly limited. , Black light lamps, microwave-excited mercury lamps, metal halide lamps, sodium lamps, halogen lamps, xenon lamps, fluorescent lamps, sunlight, electron beam irradiation devices, and the like. These light sources may be used independently and 2 or more types may be used together. In selecting these light sources, they are appropriately selected in accordance with the absorption wavelength of the photo radical polymerization initiator.
- Examples of the irradiation procedure of the light source to the adhesive for bonding the front plate for a display device of the present invention include simultaneous irradiation of various light sources, sequential irradiation with a time difference, combined irradiation of simultaneous irradiation and sequential irradiation, etc. Any irradiation means may be used.
- the lower limit of the transmittance of light having a wavelength of 405 nm when the thickness of the cured product of the adhesive for bonding a front plate for a display device of the present invention is 300 ⁇ m is 90%.
- the transmittance is less than 90%, the obtained display device may be inferior in optical characteristics.
- the cured product of the adhesive for bonding a front plate for a display element of the present invention preferably has a haze value of 2 or less when the thickness is 300 ⁇ m. When the fog value exceeds 2, the resulting display element may become cloudy.
- the haze value is more preferably 1 or less.
- Examples of the method for producing a display device using the adhesive for bonding a front plate for a display device of the present invention include, for example, the front plate or the entire surface of a substrate to which the front plate is bonded before the display device of the present invention.
- Examples include a method in which a base plate bonding adhesive is applied, the base material and the front plate are bonded via the front device bonding adhesive for display device of the present invention, and ultraviolet rays are irradiated.
- FIG. 1 is a cross-sectional view showing an example of a display device using the adhesive for bonding a front plate for a display device of the present invention.
- a front plate 1 and a base material 2 are bonded together via a display device front plate bonding adhesive 3.
- the front plate 1 has a light blocking portion 4 and a light transmitting portion 5, and the portion of the display device front plate bonding adhesive 3 located under the light blocking portion 4 is incident from the front plate side. It is difficult for the light to reach.
- the display positioned at the light-shielding portion is irradiated with light and heated.
- the adhesive for bonding the front plate for a device can be cured.
- the adhesive for bonding a front plate for a display device is cured by irradiating light and heating, the adhesive for bonding a front plate for a display device of the present invention contains the thermal radical polymerization initiator. It is preferable.
- the adhesive for bonding a front plate for a display device of the present invention may be used as an adhesive set combining two or more kinds, and has a viscosity composed of the adhesive for bonding a front plate for a display device of the present invention.
- You may seal by sticking a front board and a base material under atmospheric pressure or pressure reduction using the adhesive set for front plate bonding for display devices.
- the dam agent and the fill agent are adhesives for laminating a front plate for a display device of the present invention, each having the same monofunctional radical polymerizable compound and the monofunctional radical polymerization.
- a homopolymer of a functional compound, a polyfunctional radical polymerizable compound, and a photo radical polymerization initiator, and the dam agent has a higher content of the homopolymer of the monofunctional radical polymerizable compound than the filler, and E The viscosity of the dam agent measured under the conditions of 25 ° C.
- the “peripheral portion of the display device” means a so-called “frame” portion between the display pixel portion and the end portion of the display device in the display device.
- An agent can be obtained.
- the base material and the front plate are obtained by coating a dam agent having a high viscosity on the outside of the fill agent having a low viscosity and excellent coatability.
- the dam agent prevents the filling agent from sticking out, the transparent material is used for both the dam agent and the filling agent. Device image may be distorted.
- the dam agent and the filling agent are the adhesive for bonding a front plate for a display device of the present invention.
- the dam agent and the fill agent include a monofunctional radical polymerizable compound having a hydrophilic group and a hydrophobic group in a molecule, a homopolymer of the monofunctional radical polymerizable compound, a polyfunctional radical polymerizable compound, And a radical photopolymerization initiator.
- the dam agent and the fill agent contain the same monofunctional radical polymerizable compound and a homopolymer of the monofunctional radical polymerizable compound, and the dam agent is more monofunctional radical polymerizable than the fill agent. High content of compound homopolymer.
- the content of the monofunctional radical polymerizable compound in the dam agent is not particularly limited, the total amount of the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, and the polyfunctional radical polymerizable compound is 100 parts by weight.
- the preferred lower limit is 3 parts by weight and the preferred upper limit is 50 parts by weight.
- the content of the monofunctional radically polymerizable compound in the dam agent is less than 3 parts by weight, the viscosity of the obtained dam agent becomes too high and coating may be difficult.
- the content of the monofunctional radical polymerizable compound in the dam agent exceeds 50 parts by weight, the viscosity of the dam agent obtained becomes too low, and the dam agent or the fill agent protrudes when the base material and the front plate are bonded together. Or the dam agent may become deformed due to increased shrinkage of the dam agent.
- the minimum with more preferable content of the monofunctional radically polymerizable compound in the said dam agent is 5 weight part, and a more preferable upper limit is 30 weight part.
- the content of the monofunctional radical polymerizable compound in the filling agent is not particularly limited, but the total of the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, and the polyfunctional radical polymerizable compound is 100 parts by weight.
- the preferred lower limit is 10 parts by weight and the preferred upper limit is 95 parts by weight.
- the content of the monofunctional radically polymerizable compound in the filling agent is less than 10 parts by weight, the viscosity of the resulting filling agent becomes too high and coating may be difficult.
- the content of the monofunctional radically polymerizable compound in the filler exceeds 95 parts by weight, the curing shrinkage of the filler may be increased and deformed.
- the minimum with more preferable content of the monofunctional radically polymerizable compound in the said fill agent is 30 weight part, and a more preferable upper limit is 90 weight part.
- the dam agent has a higher content of the homopolymer of the monofunctional radical polymerizable compound than the fill agent.
- the content of the homopolymer of the monofunctional radical polymerizable compound in the dam agent is not particularly limited as long as the content ratio is higher than that of the fill agent, but the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, And a preferable minimum is 30 weight part and a preferable upper limit is 95 weight part with respect to a total of 100 weight part of a polyfunctional radically polymerizable compound.
- the content of the homopolymer of the monofunctional radically polymerizable compound in the dam agent is less than 30 parts by weight, the curing shrinkage is large, and the resulting dam agent has an adhesive property with the front plate and the substrate to which the front plate is bonded.
- the dam agent may be inferior, deformed, or the viscosity of the dam agent may be insufficient, and the dam agent or the fill agent may protrude when the base material and the front plate are bonded to each other.
- the content of the homopolymer of the monofunctional radically polymerizable compound in the dam agent exceeds 95 parts by weight, the viscosity of the dam agent becomes too high and coating may be difficult.
- the more preferable lower limit of the content of the homopolymer of the monofunctional radical polymerizable compound in the dam agent is 50 parts by weight, and the more preferable upper limit is 90 parts by weight.
- the content of the homopolymer of the monofunctional radical polymerizable compound in the fill agent is not particularly limited as long as the content ratio is lower than the dam agent, but the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, And a preferable minimum is 1 weight part and a preferable upper limit is 70 weight part with respect to a total of 100 weight part of a polyfunctional radically polymerizable compound.
- a preferable minimum is 1 weight part and a preferable upper limit is 70 weight part with respect to a total of 100 weight part of a polyfunctional radically polymerizable compound.
- the content of the homopolymer of the monofunctional radically polymerizable compound in the filler exceeds 70 parts by weight, the viscosity of the resulting filler may become too high, and coating may be difficult.
- the more preferable lower limit of the content of the homopolymer of the monofunctional radical polymerizable compound in the filling agent is 5 parts by weight, and the more preferable upper limit is 50 parts by weight.
- Viscosity of the above dam agent measured at 25 ° C. and 2.5 rpm using an E type viscometer with respect to the viscosity of the above filling agent measured at 25 ° C. and 2.5 rpm using an E type viscometer The lower limit of the ratio is three times and the upper limit is 10,000 times.
- the viscosity of the dam agent is less than 3 times the viscosity of the fill agent, the dam agent or the fill agent may protrude when the substrate and the front plate are bonded together.
- the viscosity of the dam agent exceeds 10,000 times the viscosity of the fill agent, it may be difficult to apply the dam agent, or the base material may be distorted due to a difference in curing shrinkage rate.
- the preferable lower limit of the ratio of the viscosity of the dam agent to the viscosity of the filler is 5 times, the preferable upper limit is 5000 times, the more preferable lower limit is 10 times, and the more preferable upper limit is 1000 times.
- the dam agent has a preferred lower limit of 3000 mPa ⁇ s and a preferred upper limit of 500,000 mPa ⁇ s, measured using an E-type viscometer at 25 ° C. and 2.5 rpm. If the viscosity of the dam agent is less than 3000 mPa ⁇ s, the dam agent or the fill agent may flow out during coating or when the substrate and the front plate are bonded together. When the viscosity of the dam agent exceeds 500,000 mPa ⁇ s, it may be difficult to apply the dam agent.
- the minimum with more preferable viscosity of the said dam agent is 5000 mPa * s, and a more preferable upper limit is 300,000 mPa * s.
- the above filling agent has a preferable lower limit of 10 mPa ⁇ s and a preferable upper limit of 30,000 mPa ⁇ s, as measured with an E-type viscometer under the conditions of 25 ° C. and 2.5 rpm.
- the viscosity of the filling agent is less than 10 mPa ⁇ s, curing shrinkage may be large and distortion may occur.
- the viscosity of the filler exceeds 30,000 mPa ⁇ s, it may be difficult to apply the filler.
- the more preferable lower limit of the viscosity of the adhesive for bonding a front plate for a display device is 100 mPa ⁇ s, and the more preferable upper limit is 10,000 mPa ⁇ s.
- the step of curing the dam agent and the fill agent by irradiating the dam agent and the fill agent, the dam agent and the fill agent are the dam agent and the fill of the adhesive set for laminating a front plate for display devices of the present invention.
- the manufacturing method of the display device which is an agent is also one of this invention.
- the dam agent may be applied to the front plate or applied to the base material to which the front plate is bonded. You may work.
- the thickness of the adhesive layer with the dam agent after coating is appropriately determined depending on the material, use, etc., but is usually about 1 to 200 ⁇ m.
- the method of applying the dam agent is not particularly limited, for example, a method using dispensing, screen printing or the like. Can be mentioned. Further, in the step of applying the fill agent in the frame of the applied dam agent, the method of applying the fill agent is not particularly limited, and examples thereof include methods using dispensing, screen printing, ink jet, and the like. .
- the dam agent and the fill agent are preferably applied while heating in order to apply uniformly.
- the dam agent and the fill agent are used.
- the light irradiated for curing the agent is preferably light having a wavelength of 300 nm to 400 nm and an integrated light amount of 300 to 3000 mJ / cm 2 .
- the light source for irradiating the dam agent and the light for curing the fill agent is not particularly limited. Examples include a wave excitation mercury lamp, a metal halide lamp, a sodium lamp, a halogen lamp, a xenon lamp, a fluorescent lamp, sunlight, and an electron beam irradiation device. These light sources may be used independently and 2 or more types may be used together. In selecting these light sources, they are appropriately selected in accordance with the absorption wavelength of the photo radical polymerization initiator.
- Examples of the light irradiation procedure from the light source include simultaneous irradiation of various light sources, sequential irradiation with a time lag, combined irradiation of simultaneous irradiation and sequential irradiation, and any irradiation means may be used. .
- a preferable lower limit of the transmittance of light having a wavelength of 405 nm when the thickness is 300 ⁇ m is 90%.
- the transmittance is less than 90%, the obtained display device may be inferior in optical characteristics.
- a light shielding portion such as an opaque electrode or a black matrix is formed on a base material or a front plate as in the display device shown in FIG.
- the dam agent and the fill agent located in the light shielding portion can be cured by irradiating light and heating.
- the dam agent and the fill agent preferably contain the thermal radical polymerization initiator.
- the adhesive for bonding a front plate for a display device of the present invention and the adhesive set for bonding a front plate for a display device of the present invention can be suitably used for a display device.
- the display device using the adhesive for bonding a front plate for a display device of the present invention or the adhesive set for bonding a front plate for a display device of the present invention is also one aspect of the present invention.
- the front plate and the base material are sufficiently bonded even when the transparency and the moisture resistance of the cured product are excellent and the polarity of the front plate and the base material to which the front plate is bonded is greatly different.
- An adhesive for bonding a front plate for a display device can be provided.
- the display device which uses this adhesive agent for front plate bonding for a display device can be provided.
- FIG. 1 is a cross-sectional view showing an example of a display device using the adhesive for bonding a front plate for a display device of the present invention.
- Example 1 As monofunctional radically polymerizable compounds, 40 parts by weight of phenoxydiethylene glycol acrylate (manufactured by Daicel Cytec Co., Ltd., “EBECRYL110”), 50 parts by weight of a homopolymer of phenoxydiethylene glycol acrylate (glass transition temperature—15 ° C., weight average molecular weight 30,000), 10 parts by weight of tricyclodecane dimethanol diacrylate (“IRR-214K” manufactured by Daicel Cytec Co., Ltd.) as a polyfunctional radical polymerizable compound, and 1-hydroxycyclohexyl phenyl ketone (manufactured by BASF Japan, “ “Irgacure 184”) 1 part by weight, 2 parts by weight of benzoyl peroxide (manufactured by NOF Corporation, "NIPER BW”) as a thermal radical polymerization initiator, and ⁇ -glycidoxypropylmedium as a silane coupling agent 1 part by weight
- Example 2 As a monofunctional radical polymerizable compound, 40 parts by weight of nonylphenyltetraethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “Light acrylate NP-4EA”) is blended in place of phenoxydiethylene glycol acrylate, and nonyl instead of phenoxydiethylene glycol acrylate homopolymer An adhesive for bonding a front plate for a display device was prepared in the same manner as in Example 1 except that 50 parts by weight of a homopolymer of phenyltetraethylene glycol acrylate (glass transition temperature—25 ° C., weight average molecular weight 50,000) was blended. Obtained.
- a homopolymer of phenyltetraethylene glycol acrylate glass transition temperature—25 ° C., weight average molecular weight 50,000
- Example 3 As a monofunctional radical polymerizable compound, 40 parts by weight of 2-ethylhexyl diethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “Light Acrylate EHDG-A”) is blended in place of phenoxydiethylene glycol acrylate, and instead of a homopolymer of phenoxydiethylene glycol acrylate, 2- An adhesive for bonding a front plate for a display device was obtained in the same manner as in Example 1 except that 50 parts by weight of a homopolymer of ethylhexyl diethylene glycol acrylate (glass transition temperature-30 ° C., weight average molecular weight 70,000) was blended. .
- a homopolymer of ethylhexyl diethylene glycol acrylate glass transition temperature-30 ° C., weight average molecular weight 70,000
- Example 4 Adhesion for bonding a front plate for a display device in the same manner as in Example 1 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 90 parts by weight and the blending amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 5 parts by weight. An agent was obtained.
- Example 5 Adhesion for bonding a front plate for a display device in the same manner as in Example 1 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 5 parts by weight and the blending amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 90 parts by weight. An agent was obtained.
- Example 6 The same as in Example 1 except that the amount of phenoxydiethylene glycol acrylate was changed to 49.5 parts by weight and the amount of tricyclodecane dimethanol diacrylate was changed to 0.5 parts by weight. An adhesive for laminating the face plates was obtained.
- Example 7 For pasting front plate for display device in the same manner as in Example 1 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 10 parts by weight and the blending amount of tricyclodecane dimethanol diacrylate was changed to 40 parts by weight. An adhesive was obtained.
- Example 8 A display device front plate bonding adhesive was obtained in the same manner as in Example 1 except that benzoyl peroxide was not blended.
- Example 9 As a monofunctional radical polymerizable compound, instead of phenoxydiethylene glycol acrylate, 40 parts by weight of 2-hydroxy-3-phenoxypropyl acrylate (manufactured by Kyoeisha Chemical Co., Ltd., trade name “epoxy ester M-600A”) is blended, and homopolymer of phenoxydiethylene glycol acrylate The same as in Example 1 except that 50 parts by weight of 2-hydroxy-3-phenoxypropyl acrylate homopolymer (glass transition temperature 15 ° C., weight average molecular weight 50,000) was blended instead of the polymer. An adhesive for laminating the face plates was obtained.
- 2-hydroxy-3-phenoxypropyl acrylate manufactured by Kyoeisha Chemical Co., Ltd., trade name “epoxy ester M-600A”
- homopolymer of phenoxydiethylene glycol acrylate The same as in Example 1 except that 50 parts by weight of 2-hydroxy-3-phenoxypropyl acrylate homopolymer (
- Example 10 Instead of phenoxydiethylene glycol acrylate as a monofunctional radical polymerizable compound, dicyclopentenyloxyethyl acrylate (manufactured by Hitachi Chemical Co., Ltd., “Fan”), which is a monofunctional radical polymerizable compound having a substituent represented by the formula (2-2) Kuryl FA-512AS ”)) 40 parts by weight, and instead of phenoxydiethylene glycol acrylate homopolymer, 50 parts by weight of dicyclopentenyloxyethyl acrylate homopolymer (glass transition temperature 10 ° C., weight average molecular weight 80,000) Except having done, it carried out similarly to Example 1, and obtained the adhesive agent for front plate bonding for display devices.
- dicyclopentenyloxyethyl acrylate manufactured by Hitachi Chemical Co., Ltd., “Fan”
- Kuryl FA-512AS a monofunctional radical polymerizable compound having a substituent represented by the formula (2-2) Kuryl FA-512AS
- Example 4 An adhesive for bonding a front plate for a display device was obtained in the same manner as in Example 1 except that the homopolymer of phenoxydiethylene glycol acrylate was not blended and the blending amount of phenoxydiethylene glycol acrylate was changed to 90 parts by weight.
- Example 5 As in Example 1, except that 40 parts by weight of methoxy-triethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “Light Acrylate MTG-A”) was added as a monofunctional radical polymerizable compound instead of phenoxydiethylene glycol acrylate. An adhesive for bonding a front plate for a display device was obtained.
- methoxy-triethylene glycol acrylate manufactured by Kyoeisha Chemical Co., Ltd., “Light Acrylate MTG-A”
- An adhesive for bonding a front plate for a display device was obtained.
- Example 6 An adhesive for bonding a front plate for a display device was obtained in the same manner as in Example 1 except that 50 parts by weight of a polyester resin (“Byron 500” manufactured by Toyobo Co., Ltd.) was used instead of the homopolymer of phenoxydiethylene glycol acrylate. It was.
- a polyester resin (“Byron 500” manufactured by Toyobo Co., Ltd.) was used instead of the homopolymer of phenoxydiethylene glycol acrylate. It was.
- Adhesiveness 1 (after photocuring) Using the wire bar, the adhesive for bonding the front plate for display devices obtained in Examples 1 to 10 and Comparative Examples 1 to 7 was applied onto ITO-deposited PET (manufactured by Teijin Ltd.), and glass was applied from above. Were pasted together. Next, using a metal halide lamp, the adhesive was cured by irradiating with 3000 mJ / cm 2 of ultraviolet rays to prepare a polarizing plate for evaluation. The 180 ° peel strength of the obtained polarizing plate for evaluation was measured using a universal testing machine (manufactured by Shimadzu Corporation, “EZ Graph”) under the condition of a peel rate of 5 mm / min.
- EZ Graph universal testing machine
- Adhesiveness 2 (after thermosetting) Using the wire bar, the adhesive for bonding the front plate for display devices obtained in Examples 1 to 10 and Comparative Examples 1 to 7 was applied onto ITO-deposited PET (manufactured by Teijin Ltd.), and glass was applied from above. Were pasted together. The adhesive was cured by heating at 80 ° C. for 1 hour without irradiating with ultraviolet rays, and a polarizing plate for evaluation was produced. The 180 ° peel strength of the obtained polarizing plate for evaluation was measured using a universal testing machine (manufactured by Shimadzu Corporation, “EZ Graph”) under the condition of a peel rate of 5 mm / min.
- EZ Graph universal testing machine
- Dam agent B was obtained in the same manner as in Production Example 1 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 30 parts by weight and the blending amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 65 parts by weight.
- Dam agent E was obtained in the same manner as in Production Example 1 except that the amount of phenoxydiethylene glycol acrylate was changed to 1 part by weight and the amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 94 parts by weight.
- Moisture resistant dams A to E and fill agents A to E of the cured product were irradiated with 3000 mJ / cm 2 of ultraviolet rays to produce a film having a thickness of 300 ⁇ m, and the resulting film was 85 ° C., 85% RH For 500 hours. After removing the film from the thermostatic chamber, it is visually confirmed. When the film is transparent and transparent, “ ⁇ ” is indicated. When the film is slightly observed, “ ⁇ ” is indicated. The moisture resistance of the cured product was evaluated as “x”.
- Adhesive dam agents A to E and fill agents A to E were applied onto ITO-deposited PET (manufactured by Teijin Ltd.) using a wire bar, and glass was laminated thereon. Next, using a metal halide lamp, the adhesive was cured by irradiating with 3000 mJ / cm 2 of ultraviolet rays to prepare a polarizing plate for evaluation. The 180 ° peel strength of the obtained polarizing plate for evaluation was measured using a universal testing machine (manufactured by Shimadzu Corporation, “EZ Graph”) under the condition of a peel rate of 5 mm / min.
- Example 11 The dam agent A was applied in a frame shape to the periphery of the liquid crystal panel using a dispenser (manufactured by Musashi Engineering, “Shot Master 3”). Next, the fill agent A was applied in the frame of the dam agent A of the liquid crystal panel using a dispenser. A glass plate (non-alkali glass, thickness 0.7 mm) is bonded to the liquid crystal panel coated with the dam agent A and the fill agent A as a front plate and irradiated with 3000 mJ / cm 2 ultraviolet rays using a metal halide lamp. Agent A and Fill agent A were cured to produce a display device. When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
- Example 12 A display device was produced in the same manner as in Example 11 except that the filler B was used instead of the filler A. When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
- Example 13 A display device was produced in the same manner as in Example 11 except that the dam agent B was used instead of the dam agent A. When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
- Example 14 A display device was produced in the same manner as in Example 11 except that the filler B was used instead of the filler A and the dam agent B was used instead of the dam agent A. When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
- Example 15 A display device was produced in the same manner as in Example 11 except that the fill agent C was used instead of the fill agent A, and the dam agent C was used instead of the dam agent A. When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
- Example 16 A display device was produced in the same manner as in Example 11 except that the fill agent D was used instead of the fill agent A, and the dam agent D was used instead of the dam agent A. When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
- Example 17 The dam agent A was applied in a frame shape to the periphery of the liquid crystal panel using a dispenser (manufactured by Musashi Engineering, “Shot Master 3”). Next, the fill agent A was applied in the frame of the dam agent A of the liquid crystal panel using a dispenser. A liquid crystal panel coated with the dam agent A and the fill agent A is bonded to a glass plate (non-alkali glass, thickness 0.7 mm) provided with a light-shielding portion that does not transmit light as a front plate, and a metal halide lamp is used. The dam agent A and the fill agent A were cured by irradiating ultraviolet rays of 3000 mJ / cm 2 . Next, by heating at 60 ° C.
- the portion of the dam agent A and the fill agent A that were shielded by the light shielding portion were cured, and a display device was produced.
- the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
- the front plate and the base material are sufficiently bonded even when the transparency and the moisture resistance of the cured product are excellent and the polarity of the front plate and the base material to which the front plate is bonded is greatly different.
- An adhesive for bonding a front plate for a display device can be provided.
- the display device which uses this adhesive agent for front plate bonding for a display device can be provided.
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Abstract
Description
更に、従来の接着剤は、前面板と前面板を貼り合わせる基材との極性が大きく異なる場合の接着性に劣り、前面板に剥離が生じることがあるという問題があった。 As an adhesive having good affinity with a hydrophilic substrate, for example, Patent Document 3 discloses a resin composition containing an alkyl acrylate and an acrylate having a hydroxyl group. However, since the resin composition disclosed in Patent Document 3 is a mixture of resins having different polarities, there is a problem in compatibility, and the cured product is exposed to light, particularly when exposed to a high humidity environment. There was a problem that it was easily clouded.
Furthermore, the conventional adhesive has a problem that the front plate may be peeled off due to poor adhesion when the polarity of the front plate and the substrate to which the front plate is bonded is greatly different.
以下に本発明を詳述する。 The present invention is an adhesive used for bonding a substrate of a display device to a front plate, a monofunctional radical polymerizable compound having a hydrophilic group and a hydrophobic group in the molecule, and the monofunctional radical polymerizable compound An adhesive for bonding a front plate for a display device, comprising a homopolymer of the compound, a polyfunctional radical polymerizable compound, and a photo radical polymerization initiator.
The present invention is described in detail below.
式(2-2)で表される置換基を有する単官能ラジカル重合性化合物としては、例えば、ジシクロペンテニルオキシエチルアクリレート(日立化成社製、「ファンクリルFA-512AS」)等が挙げられる。 Examples of the monofunctional radically polymerizable compound having a substituent represented by the formula (2-1) include phenoxyethyl acrylate (manufactured by Kyoeisha Chemical Co., “Light Acrylate PO-A”, Daicel Cytec Co., Ltd., “EBECRYL110”). ), Phenyldiethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “light acrylate P-200A”), nonylphenol EO adduct acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “light acrylate NP-4EA”), 2-hydroxy-3-phenoxypropyl acrylate ( And “Epoxy ester M-600A” manufactured by Kyoeisha Chemical Co., Ltd.).
Examples of the monofunctional radically polymerizable compound having a substituent represented by the formula (2-2) include dicyclopentenyloxyethyl acrylate (manufactured by Hitachi Chemical Co., Ltd., “Fancryl FA-512AS”).
なお、GPCよってポリスチレン換算による重量平均分子量を測定する際のカラムとしては、例えば、LF-804(SHOKO社製)等が挙げられる。 The preferable lower limit of the weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC) of the homopolymer of the monofunctional radical polymerizable compound is 3000, and the preferable upper limit is 200,000. When the weight average molecular weight of the homopolymer of the monofunctional radically polymerizable compound is less than 3000, the obtained adhesive for bonding a front plate for a display device is inferior in adhesiveness to a front plate or a substrate, The viscosity may be insufficient. When the weight average molecular weight of the homopolymer of the monofunctional radically polymerizable compound exceeds 200,000, the viscosity of the obtained adhesive for bonding a front plate for a display device becomes too high, and coating may be difficult. The minimum with a more preferable weight average molecular weight of the homopolymer of the said monofunctional radically polymerizable compound is 20,000, and a more preferable upper limit is 80,000.
An example of a column for measuring the weight average molecular weight in terms of polystyrene by GPC is LF-804 (manufactured by SHOKO).
なかでも、親水性基と疎水性基を分子内に有することから、トリシクロデカンジメタノールジアクリレートが好ましい。 Examples of the polyfunctional radical polymerizable compound include polyfunctional epoxy acrylates such as bisphenol A diglycidyl ether diacrylate and polyethylene glycol diglycidyl ether diacrylate, trimethylolpropane triacrylate, tetramethylolmethane tetraacrylate, and pentaerythritol triacrylate. Acrylate, pentaerythritol tetraacrylate, dipentaerythritol monohydroxypentaacrylate, dipentaerythritol hexaacrylate, 1,4-butylene glycol diacrylate, 1,6-hexanediol diacrylate, polyethylene glycol diacrylate, polypropylene diacrylate, tricyclo Examples include decane dimethanol diacrylate. These polyfunctional radically polymerizable compounds may be used alone or in combination of two or more.
Of these, tricyclodecane dimethanol diacrylate is preferred because it has a hydrophilic group and a hydrophobic group in the molecule.
光ラジカル重合開始剤は特に限定されず、例えば、ベンゾフェノン系化合物、アセトフェノン系化合物、アシルフォスフィンオキサイド系化合物、チタノセン系化合物、オキシムエステル系化合物、ベンゾインエーテル系化合物、チオキサントン等が挙げられる。 The adhesive for bonding a front plate for a display device of the present invention contains a radical photopolymerization initiator.
The radical photopolymerization initiator is not particularly limited, and examples thereof include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, and thioxanthone.
上記熱ラジカル重合開始剤としては、100℃以下の温度で分解してラジカルを生ずるものであればいずれも使用可能であり、成膜加工温度、架橋温度、貯蔵安定性等を考慮して選択して使用することができる。なかでも、半減期10時間の分解温度が70℃以下のものが、低温硬化性が良いことから好適に使用される。
上記熱ラジカル重合開始剤としては、例えば、アゾ化合物、有機過酸化物等が挙げられる。なかでも、有機過酸化物が好ましい。 The adhesive for bonding a front plate for a display device of the present invention preferably contains a thermal radical polymerization initiator.
Any thermal radical polymerization initiator may be used as long as it decomposes at a temperature of 100 ° C. or lower to generate radicals, and is selected in consideration of the film forming temperature, the crosslinking temperature, the storage stability, and the like. Can be used. Among these, those having a decomposition temperature of 70 ° C. or less with a half-life of 10 hours are preferably used because of low temperature curability.
Examples of the thermal radical polymerization initiator include azo compounds and organic peroxides. Of these, organic peroxides are preferable.
上記シランカップリング剤としては、具体的には例えば、ビニルトリエトキシシラン、ビニルトリス(β-メトキシエトキシ)シラン、γ-メタクリロキシプロピルトリメトキシシラン、ビニルトリアセトキシシラン、γ-グリシドキシプロピルトリメトキシシラン、γ-グリシドキシプロピルトリエトキシシラン、β-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン、γ-クロロプロピルメトキシシラン、ビニルトリクロロシラン、γ-メルカプトプロピルトリメトキシシラン、γ-アミノプロピルトリエトキシシラン、N-β(アミノエチル)-γ-アミノプロピルトリメトキシシラン等が挙げられる。これらのシランカップリング剤は単独で用いてもよいし、2種以上を併用してもよい。 The adhesive for bonding a front plate for a display device of the present invention may contain a silane coupling agent as an adhesion promoter as long as the object of the present invention is not impaired.
Specific examples of the silane coupling agent include vinyltriethoxysilane, vinyltris (β-methoxyethoxy) silane, γ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, and γ-glycidoxypropyltrimethoxy. Silane, γ-glycidoxypropyltriethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-chloropropylmethoxysilane, vinyltrichlorosilane, γ-mercaptopropyltrimethoxysilane, γ-aminopropyl And triethoxysilane, N-β (aminoethyl) -γ-aminopropyltrimethoxysilane, and the like. These silane coupling agents may be used alone or in combination of two or more.
上記充填剤は特に限定されず、例えば、無機フィラー、有機フィラー等が挙げられる。
上記無機フィラーは特に限定されず、例えば、タルク、シリカ、スメクタイト、ベントナイト、炭酸カルシウム、炭酸マグネシウム、アルミナ、モンモリロナイト、珪藻土、酸化マグネシウム、酸化チタン、水酸化マグネシウム、水酸化アルミニウム、ガラスビーズ、硫酸バリウム、石膏、珪酸カルシウム、セリサイト活性白土等が挙げられる。
上記有機フィラーは特に限定されず、例えば、ポリエステル微粒子、ポリウレタン微粒子、ビニル重合体微粒子、アクリル重合体微粒子等が挙げられる。
これらの充填剤は単独で用いてもよいし、2種以上を併用してもよい。 The adhesive for bonding a front plate for a display device of the present invention may contain a filler as long as the object of the present invention is not impaired.
The said filler is not specifically limited, For example, an inorganic filler, an organic filler, etc. are mentioned.
The inorganic filler is not particularly limited. For example, talc, silica, smectite, bentonite, calcium carbonate, magnesium carbonate, alumina, montmorillonite, diatomaceous earth, magnesium oxide, titanium oxide, magnesium hydroxide, aluminum hydroxide, glass beads, barium sulfate. , Gypsum, calcium silicate, sericite activated clay and the like.
The organic filler is not particularly limited, and examples thereof include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, and acrylic polymer fine particles.
These fillers may be used independently and may use 2 or more types together.
また、上記前面板を貼り合わせる基材としては、液晶パネルモジュール、有機ELパネルモジュール、プラズマディスプレイ、電子ペーパー等が挙げられる。
更に、本発明の表示デバイス用前面板貼り合わせ用接着剤は、異なる前面板同士の接着にも使用できる。 Examples of the front plate include a protective panel made of glass, polycarbonate, acrylic, or the like, a resistive or capacitive touch panel, a lenticular lens for 3D display, a barrier liquid crystal panel called a parallax barrier, and the like. .
Examples of the substrate on which the front plate is bonded include a liquid crystal panel module, an organic EL panel module, a plasma display, and electronic paper.
Furthermore, the front plate bonding adhesive for display devices of the present invention can also be used for bonding different front plates.
本発明の表示素子用前面板貼り合わせ用接着剤の硬化物は、厚さを300μmとしたときの曇値(ヘーズ)が2以下であることが好ましい。上記曇値が2を超えると、得られる表示素子が濁ったものとなることがある。上記曇値は、1以下であることがより好ましい。 The lower limit of the transmittance of light having a wavelength of 405 nm when the thickness of the cured product of the adhesive for bonding a front plate for a display device of the present invention is 300 μm is 90%. When the transmittance is less than 90%, the obtained display device may be inferior in optical characteristics.
The cured product of the adhesive for bonding a front plate for a display element of the present invention preferably has a haze value of 2 or less when the thickness is 300 μm. When the fog value exceeds 2, the resulting display element may become cloudy. The haze value is more preferably 1 or less.
図1に示した表示デバイスのように、基材や前面板に不透明電極やブラックマトリックス等の遮光部が形成されている場合、光を照射するとともに、加熱することにより、遮光部に位置する表示デバイス用前面板貼り合わせ用接着剤を硬化させることができる。
光を照射するとともに、加熱することにより、表示デバイス用前面板貼り合わせ用接着剤を硬化させる場合、本発明の表示デバイス用前面板貼り合わせ用接着剤は、上記熱ラジカル重合開始剤を含有することが好ましい。 FIG. 1 is a cross-sectional view showing an example of a display device using the adhesive for bonding a front plate for a display device of the present invention. In the display device shown in FIG. 1, a
As in the display device shown in FIG. 1, when a light-shielding portion such as an opaque electrode or a black matrix is formed on a base material or a front plate, the display positioned at the light-shielding portion is irradiated with light and heated. The adhesive for bonding the front plate for a device can be cured.
In the case where the adhesive for bonding a front plate for a display device is cured by irradiating light and heating, the adhesive for bonding a front plate for a display device of the present invention contains the thermal radical polymerization initiator. It is preferable.
表示デバイスの基材と前面板との貼り合わせに用いる接着剤であって、表示デバイスの周辺部において基材と前面板とを接着するダム剤と、上記ダム剤の内側において基材と前面板とを接着するフィル剤とからなり、上記ダム剤及び上記フィル剤は、本発明の表示デバイス用前面板貼り合わせ用接着剤であって、それぞれ同じ単官能ラジカル重合性化合物、該単官能ラジカル重合性化合物のホモポリマー、多官能ラジカル重合性化合物、及び、光ラジカル重合開始剤を含有し、上記ダム剤は、上記フィル剤よりも単官能ラジカル重合性化合物のホモポリマーの含有割合が高く、E型粘度計を用いて、25℃、2.5rpmの条件で測定した上記ダム剤の粘度が、E型粘度計を用いて、25℃、2.5rpmの条件で測定した上記フィル剤の粘度の3~1万倍である表示デバイス用前面板貼り合わせ用接着剤セットもまた、本発明の1つである。
なお、本明細書において、「表示デバイスの周辺部」とは、表示デバイスにおける表示画素部から表示デバイス端部までの間のいわゆる「額縁」の部分を意味する。 Further, the adhesive for bonding a front plate for a display device of the present invention may be used as an adhesive set combining two or more kinds, and has a viscosity composed of the adhesive for bonding a front plate for a display device of the present invention. A high peripheral adhesive (dam agent) and a filling adhesive (fill agent) made of the adhesive for bonding a front plate for a display device of the present invention having a lower viscosity than the peripheral adhesive to fill the inside. You may seal by sticking a front board and a base material under atmospheric pressure or pressure reduction using the adhesive set for front plate bonding for display devices.
An adhesive used for bonding a base material and a front plate of a display device, the dam agent bonding the base material and the front plate at the periphery of the display device, and the base material and the front plate inside the dam agent The dam agent and the fill agent are adhesives for laminating a front plate for a display device of the present invention, each having the same monofunctional radical polymerizable compound and the monofunctional radical polymerization. A homopolymer of a functional compound, a polyfunctional radical polymerizable compound, and a photo radical polymerization initiator, and the dam agent has a higher content of the homopolymer of the monofunctional radical polymerizable compound than the filler, and E The viscosity of the dam agent measured under the conditions of 25 ° C. and 2.5 rpm using a mold viscometer is the viscosity of the fill agent measured under the conditions of 25 ° C. and 2.5 rpm using an E type viscometer. 3 to 10,000 times the adhesive sets for bonding a front panel for a display device is also one of the present invention.
In the present specification, the “peripheral portion of the display device” means a so-called “frame” portion between the display pixel portion and the end portion of the display device in the display device.
また、上記ダム剤及び上記フィル剤は、同じ単官能ラジカル重合性化合物、及び、該単官能ラジカル重合性化合物のホモポリマーを含有し、上記ダム剤は、上記フィル剤よりも単官能ラジカル重合性化合物のホモポリマーの含有割合が高い。 In the adhesive set for bonding a front plate for a display device of the present invention, the dam agent and the filling agent are the adhesive for bonding a front plate for a display device of the present invention. That is, the dam agent and the fill agent include a monofunctional radical polymerizable compound having a hydrophilic group and a hydrophobic group in a molecule, a homopolymer of the monofunctional radical polymerizable compound, a polyfunctional radical polymerizable compound, And a radical photopolymerization initiator.
Further, the dam agent and the fill agent contain the same monofunctional radical polymerizable compound and a homopolymer of the monofunctional radical polymerizable compound, and the dam agent is more monofunctional radical polymerizable than the fill agent. High content of compound homopolymer.
上記ダム剤における単官能ラジカル重合性化合物のホモポリマーの含有量は、上記フィル剤よりも含有割合が高ければ特に限定されないが、単官能ラジカル重合性化合物、単官能ラジカル重合性化合物のホモポリマー、及び、多官能ラジカル重合性化合物の合計100重量部に対して、好ましい下限は30重量部、好ましい上限は95重量部である。上記ダム剤における単官能ラジカル重合性化合物のホモポリマーの含有量が30重量部未満であると、硬化収縮が大きく、得られるダム剤が前面板や前面板を貼り合わせる基材との接着性に劣るものとなったり、変形したり、ダム剤の粘度が不充分となってダム剤やフィル剤が基材と前面板とを貼り合わせる際にはみ出したりすることがある。上記ダム剤における単官能ラジカル重合性化合物のホモポリマーの含有量が95重量部を超えると、ダム剤の粘度が高くなりすぎ、塗工が困難になることがある。上記ダム剤における単官能ラジカル重合性化合物のホモポリマーの含有量のより好ましい下限は50重量部、より好ましい上限は90重量部である。 The dam agent has a higher content of the homopolymer of the monofunctional radical polymerizable compound than the fill agent.
The content of the homopolymer of the monofunctional radical polymerizable compound in the dam agent is not particularly limited as long as the content ratio is higher than that of the fill agent, but the monofunctional radical polymerizable compound, the homopolymer of the monofunctional radical polymerizable compound, And a preferable minimum is 30 weight part and a preferable upper limit is 95 weight part with respect to a total of 100 weight part of a polyfunctional radically polymerizable compound. When the content of the homopolymer of the monofunctional radically polymerizable compound in the dam agent is less than 30 parts by weight, the curing shrinkage is large, and the resulting dam agent has an adhesive property with the front plate and the substrate to which the front plate is bonded. The dam agent may be inferior, deformed, or the viscosity of the dam agent may be insufficient, and the dam agent or the fill agent may protrude when the base material and the front plate are bonded to each other. When the content of the homopolymer of the monofunctional radically polymerizable compound in the dam agent exceeds 95 parts by weight, the viscosity of the dam agent becomes too high and coating may be difficult. The more preferable lower limit of the content of the homopolymer of the monofunctional radical polymerizable compound in the dam agent is 50 parts by weight, and the more preferable upper limit is 90 parts by weight.
また、上記塗工したダム剤の枠内にフィル剤を塗工する工程において、上記フィル剤を塗工する方法は特に限定されず、例えば、ディスペンス、スクリーン印刷、インクジェット等を用いる方法が挙げられる。
上記ダム剤及び上記フィル剤は、均一に塗工するために、加熱しながら塗工することが好ましい。 In the step of applying the dam agent in a frame shape to at least one peripheral part of the base material and the front plate, the method of applying the dam agent is not particularly limited, for example, a method using dispensing, screen printing or the like. Can be mentioned.
Further, in the step of applying the fill agent in the frame of the applied dam agent, the method of applying the fill agent is not particularly limited, and examples thereof include methods using dispensing, screen printing, ink jet, and the like. .
The dam agent and the fill agent are preferably applied while heating in order to apply uniformly.
光を照射するとともに、加熱することにより、上記ダム剤や上記フィル剤を硬化させる場合、上記ダム剤及び上記フィル剤は、上記熱ラジカル重合開始剤を含有することが好ましい。 When using the adhesive set for laminating a front plate for a display device of the present invention, a light shielding portion such as an opaque electrode or a black matrix is formed on a base material or a front plate as in the display device shown in FIG. In this case, the dam agent and the fill agent located in the light shielding portion can be cured by irradiating light and heating.
When the dam agent and the fill agent are cured by irradiating light and heating, the dam agent and the fill agent preferably contain the thermal radical polymerization initiator.
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレート(ダイセルサイテック社製、「EBECRYL110」)40重量部と、フェノキシジエチレングリコールアクリレートのホモポリマー(ガラス転移温度-15℃、重量平均分子量3万)50重量部と、多官能ラジカル重合性化合物としてトリシクロデカンジメタノールジアクリレート(ダイセルサイテック社製、「IRR-214K」)10重量部と、光ラジカル重合開始剤として1-ヒドロキシシクロヘキシルフェニルケトン(BASF Japan社製、「イルガキュア184」)1重量部と、熱ラジカル重合開始剤としてベンゾイルパーオキサイド(日油社製、「ナイパーBW」)2重量部と、シランカップリング剤としてγ-グリシドキシプロピルメチルジエトキシシラン(信越シリコーン社製、「KBM-403」)1重量部とを、ホモディスパー型攪拌混合機(プライミクス社製、「ホモディスパーL型」)を用い、攪拌速度3000rpmで均一に攪拌混合して表示デバイス用前面板貼り合わせ用接着剤を得た。 Example 1
As monofunctional radically polymerizable compounds, 40 parts by weight of phenoxydiethylene glycol acrylate (manufactured by Daicel Cytec Co., Ltd., “EBECRYL110”), 50 parts by weight of a homopolymer of phenoxydiethylene glycol acrylate (glass transition temperature—15 ° C., weight average molecular weight 30,000), 10 parts by weight of tricyclodecane dimethanol diacrylate (“IRR-214K” manufactured by Daicel Cytec Co., Ltd.) as a polyfunctional radical polymerizable compound, and 1-hydroxycyclohexyl phenyl ketone (manufactured by BASF Japan, “ "Irgacure 184") 1 part by weight, 2 parts by weight of benzoyl peroxide (manufactured by NOF Corporation, "NIPER BW") as a thermal radical polymerization initiator, and γ-glycidoxypropylmedium as a
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレートに代えてノニルフェニルテトラエチレングリコールアクリレート(共栄社化学社製、「ライトアクリレートNP-4EA」)40重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えてノニルフェニルテトラエチレングリコールアクリレートのホモポリマー(ガラス転移温度-25℃、重量平均分子量5万)50重量部を配合したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Example 2)
As a monofunctional radical polymerizable compound, 40 parts by weight of nonylphenyltetraethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “Light acrylate NP-4EA”) is blended in place of phenoxydiethylene glycol acrylate, and nonyl instead of phenoxydiethylene glycol acrylate homopolymer An adhesive for bonding a front plate for a display device was prepared in the same manner as in Example 1 except that 50 parts by weight of a homopolymer of phenyltetraethylene glycol acrylate (glass transition temperature—25 ° C., weight average molecular weight 50,000) was blended. Obtained.
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレートに代えて2-エチルヘキシルジエチレングリコールアクリレート(共栄社化学社製、「ライトアクリレートEHDG-A」)40重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えて2-エチルヘキシルジエチレングリコールアクリレートのホモポリマー(ガラス転移温度-30℃、重量平均分子量7万)50重量部を配合したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Example 3)
As a monofunctional radical polymerizable compound, 40 parts by weight of 2-ethylhexyl diethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “Light Acrylate EHDG-A”) is blended in place of phenoxydiethylene glycol acrylate, and instead of a homopolymer of phenoxydiethylene glycol acrylate, 2- An adhesive for bonding a front plate for a display device was obtained in the same manner as in Example 1 except that 50 parts by weight of a homopolymer of ethylhexyl diethylene glycol acrylate (glass transition temperature-30 ° C., weight average molecular weight 70,000) was blended. .
フェノキシジエチレングリコールアクリレートの配合量を90重量部に変更し、フェノキシジエチレングリコールアクリレートのホモポリマーの配合量を5重量部に変更したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Example 4)
Adhesion for bonding a front plate for a display device in the same manner as in Example 1 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 90 parts by weight and the blending amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 5 parts by weight. An agent was obtained.
フェノキシジエチレングリコールアクリレートの配合量を5重量部に変更し、フェノキシジエチレングリコールアクリレートのホモポリマーの配合量を90重量部に変更したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Example 5)
Adhesion for bonding a front plate for a display device in the same manner as in Example 1 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 5 parts by weight and the blending amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 90 parts by weight. An agent was obtained.
フェノキシジエチレングリコールアクリレートの配合量を49.5重量部に変更し、トリシクロデカンジメタノールジアクリレートの配合量を0.5重量部に変更したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Example 6)
The same as in Example 1 except that the amount of phenoxydiethylene glycol acrylate was changed to 49.5 parts by weight and the amount of tricyclodecane dimethanol diacrylate was changed to 0.5 parts by weight. An adhesive for laminating the face plates was obtained.
フェノキシジエチレングリコールアクリレートの配合量を10重量部に変更し、トリシクロデカンジメタノールジアクリレートの配合量を40重量部に変更したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Example 7)
For pasting front plate for display device in the same manner as in Example 1 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 10 parts by weight and the blending amount of tricyclodecane dimethanol diacrylate was changed to 40 parts by weight. An adhesive was obtained.
ベンゾイルパーオキサイドを配合しなかったこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Example 8)
A display device front plate bonding adhesive was obtained in the same manner as in Example 1 except that benzoyl peroxide was not blended.
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレートに代えて2-ヒドロキシ-3-フェノキシプロピルアクリレート(共栄社化学社製、商品名「エポキシエステルM-600A」)40重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えて2-ヒドロキシ-3-フェノキシプロピルアクリレートのホモポリマー(ガラス転移温度15℃、重量平均分子量5万)50重量部を配合したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 Example 9
As a monofunctional radical polymerizable compound, instead of phenoxydiethylene glycol acrylate, 40 parts by weight of 2-hydroxy-3-phenoxypropyl acrylate (manufactured by Kyoeisha Chemical Co., Ltd., trade name “epoxy ester M-600A”) is blended, and homopolymer of phenoxydiethylene glycol acrylate The same as in Example 1 except that 50 parts by weight of 2-hydroxy-3-phenoxypropyl acrylate homopolymer (glass transition temperature 15 ° C., weight average molecular weight 50,000) was blended instead of the polymer. An adhesive for laminating the face plates was obtained.
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレートに代えて、式(2-2)で表される置換基を有する単官能ラジカル重合性化合物であるジシクロペンテニルオキシエチルアクリレート(日立化成社製、「ファンクリルFA-512AS」)40重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えて、ジシクロペンテニルオキシエチルアクリレートのホモポリマー(ガラス転移温度10℃、重量平均分子量8万)50重量部を配合したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Example 10)
Instead of phenoxydiethylene glycol acrylate as a monofunctional radical polymerizable compound, dicyclopentenyloxyethyl acrylate (manufactured by Hitachi Chemical Co., Ltd., “Fan”), which is a monofunctional radical polymerizable compound having a substituent represented by the formula (2-2) Kuryl FA-512AS ”)) 40 parts by weight, and instead of phenoxydiethylene glycol acrylate homopolymer, 50 parts by weight of dicyclopentenyloxyethyl acrylate homopolymer (glass transition temperature 10 ° C., weight average molecular weight 80,000) Except having done, it carried out similarly to Example 1, and obtained the adhesive agent for front plate bonding for display devices.
フェノキシジエチレングリコールアクリレートを配合せず、トリシクロデカンジメタノールジアクリレートの配合量を50重量部に変更したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Comparative Example 1)
An adhesive for bonding a front plate for a display device was obtained in the same manner as in Example 1 except that phenoxydiethylene glycol acrylate was not blended and the blending amount of tricyclodecane dimethanol diacrylate was changed to 50 parts by weight.
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレートに代えてメトキシ-トリエチレングリコールアクリレート(共栄社化学社製、「ライトアクリレートMTG-A」)40重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えてメトキシ-トリエチレングリコールアクリレートのホモポリマー(ガラス転移温度-50℃、重量平均分子量4万)50重量部を配合したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Comparative Example 2)
As a monofunctional radical polymerizable compound, 40 parts by weight of methoxy-triethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “Light Acrylate MTG-A”) is blended instead of phenoxydiethylene glycol acrylate, and methoxy is substituted for the homopolymer of phenoxydiethylene glycol acrylate. -An adhesive for bonding a front plate for a display device was prepared in the same manner as in Example 1 except that 50 parts by weight of a homopolymer of triethylene glycol acrylate (glass transition temperature-50 ° C, weight average molecular weight 40,000) was blended. Obtained.
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレートに代えて2-エチルヘキシルアクリレート(東京化成社製)40重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えて2-エチルヘキシルアクリレートのホモポリマー(ガラス転移温度-50℃)50重量部を配合したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Comparative Example 3)
As a monofunctional radical polymerizable compound, 40 parts by weight of 2-ethylhexyl acrylate (manufactured by Tokyo Chemical Industry Co., Ltd.) is blended instead of phenoxydiethylene glycol acrylate, and a homopolymer of 2-ethylhexyl acrylate (glass transition temperature) is used instead of the homopolymer of phenoxydiethylene glycol acrylate. (-50 ° C.) A display device front plate bonding adhesive was obtained in the same manner as in Example 1 except that 50 parts by weight was blended.
フェノキシジエチレングリコールアクリレートのホモポリマーを配合せず、フェノキシジエチレングリコールアクリレートの配合量を90重量部に変更したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Comparative Example 4)
An adhesive for bonding a front plate for a display device was obtained in the same manner as in Example 1 except that the homopolymer of phenoxydiethylene glycol acrylate was not blended and the blending amount of phenoxydiethylene glycol acrylate was changed to 90 parts by weight.
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレートに代えてメトキシ-トリエチレングリコールアクリレート(共栄社化学社製、「ライトアクリレートMTG-A」)40重量部を配合したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Comparative Example 5)
As in Example 1, except that 40 parts by weight of methoxy-triethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “Light Acrylate MTG-A”) was added as a monofunctional radical polymerizable compound instead of phenoxydiethylene glycol acrylate. An adhesive for bonding a front plate for a display device was obtained.
フェノキシジエチレングリコールアクリレートのホモポリマーに代えてポリエステル樹脂(東洋紡社製、「バイロン500」)50重量部を配合したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Comparative Example 6)
An adhesive for bonding a front plate for a display device was obtained in the same manner as in Example 1 except that 50 parts by weight of a polyester resin (“Byron 500” manufactured by Toyobo Co., Ltd.) was used instead of the homopolymer of phenoxydiethylene glycol acrylate. It was.
トリシクロデカンジメタノールジアクリレートを配合せず、フェノキシジエチレングリコールアクリレートの配合量を50重量部に変更したこと以外は、実施例1と同様にして表示デバイス用前面板貼り合わせ用接着剤を得た。 (Comparative Example 7)
An adhesive for attaching a front plate for a display device was obtained in the same manner as in Example 1 except that tricyclodecane dimethanol diacrylate was not blended and the blending amount of phenoxydiethylene glycol acrylate was changed to 50 parts by weight.
実施例1~10及び比較例1~7で得られた表示デバイス用前面板貼り合わせ用接着剤について以下の評価を行った。結果を表1、2に示した。 <Evaluation>
The following evaluations were performed on the adhesives for bonding the front plates for display devices obtained in Examples 1 to 10 and Comparative Examples 1 to 7. The results are shown in Tables 1 and 2.
E型粘度計を用いて、25℃、2.5rpmの条件で、実施例1~10及び比較例1~7で得られた表示デバイス用前面板貼り合わせ用接着剤の粘度を測定した。 (1) Viscosity of the adhesive for adhering the front plate for display devices obtained in Examples 1 to 10 and Comparative Examples 1 to 7 under the conditions of 25 ° C. and 2.5 rpm using an E-type viscometer. It was measured.
実施例1~10及び比較例1~7で得られた表示デバイス用前面板貼り合わせ用接着剤を目視で観察し、透明な場合を「○」、不透明な場合を「×」としてモノマー成分とポリマー成分との相溶性を評価した。 (2) Compatibility The adhesives for bonding the front plate for display devices obtained in Examples 1 to 10 and Comparative Examples 1 to 7 were visually observed. The compatibility between the monomer component and the polymer component was evaluated.
実施例1~10及び比較例1~7で得られた表示デバイス用前面板貼り合わせ用接着剤に3000mJ/cm2の紫外線を照射して厚さ300μmのフィルムを作製し、波長405nmの光の透過率が90%以上の場合を「○」、90%未満の場合を「×」として透明性を評価した。 (3) Transparency of cured product A film having a thickness of 300 μm was obtained by irradiating 3000 mJ / cm 2 of ultraviolet rays to the adhesive for bonding the front plate for display devices obtained in Examples 1 to 10 and Comparative Examples 1 to 7. The transparency was evaluated with “◯” when the transmittance of light having a wavelength of 405 nm was 90% or more and “X” when the transmittance was less than 90%.
実施例1~10及び比較例1~7で得られた表示デバイス用前面板貼り合わせ用接着剤に3000mJ/cm2の紫外線を照射して厚さ300μmのフィルムを作製し、得られたフィルムを85℃、85%RHの恒温槽に500時間静置した。フィルムを恒温槽から取り出した後、目視にて確認し、白濁が見られず、透明であった場合を「○」、白濁がわずかに見られた場合を「△」、白濁がはっきりと見られた場合を「×」として硬化物の耐湿性を評価した。
なお、比較例1で得られた表示デバイス用前面板貼り合わせ用接着剤を用いた場合は、耐湿性の評価を行うことができなかった。 (4) Moisture resistance of cured product The adhesive for bonding the front plate for display devices obtained in Examples 1 to 10 and Comparative Examples 1 to 7 was irradiated with 3000 mJ / cm 2 of ultraviolet light to form a film having a thickness of 300 μm. The prepared film was allowed to stand in a constant temperature bath at 85 ° C. and 85% RH for 500 hours. After removing the film from the thermostatic chamber, it is visually confirmed. When the film is transparent and transparent, “◯” is indicated. When the film is slightly observed, “△” is indicated. The moisture resistance of the cured product was evaluated as “x”.
In addition, when the adhesive for a display device front plate bonding obtained in Comparative Example 1 was used, the moisture resistance could not be evaluated.
実施例1~10及び比較例1~7で得られた表示デバイス用前面板貼り合わせ用接着剤を、ワイヤーバーを用いて、ITO蒸着PET(帝人社製)上に塗布し、その上からガラスを貼り合わせた。次いで、メタルハライドランプを用いて、3000mJ/cm2の紫外線を照射して接着剤を硬化させ、評価用偏光板を作製した。
得られた評価用偏光板の180°剥離強度を、万能試験機(島津製作所社製、「EZグラフ」)を用いて、剥離速度5mm/分の条件で測定した。剥離強度が50N/25mm以上であった場合を「○」、20N/25mm以上50N/25mm未満であった場合を「△」、20N/25mm未満であった場合を「×」として接着性を評価した。 (5) Adhesiveness 1 (after photocuring)
Using the wire bar, the adhesive for bonding the front plate for display devices obtained in Examples 1 to 10 and Comparative Examples 1 to 7 was applied onto ITO-deposited PET (manufactured by Teijin Ltd.), and glass was applied from above. Were pasted together. Next, using a metal halide lamp, the adhesive was cured by irradiating with 3000 mJ / cm 2 of ultraviolet rays to prepare a polarizing plate for evaluation.
The 180 ° peel strength of the obtained polarizing plate for evaluation was measured using a universal testing machine (manufactured by Shimadzu Corporation, “EZ Graph”) under the condition of a peel rate of 5 mm / min. The case where the peel strength was 50 N / 25 mm or more was evaluated as “◯”, the case where it was 20 N / 25 mm or more and less than 50 N / 25 mm as “Δ”, and the case where it was less than 20 N / 25 mm as “X”. did.
実施例1~10及び比較例1~7で得られた表示デバイス用前面板貼り合わせ用接着剤を、ワイヤーバーを用いて、ITO蒸着PET(帝人社製)上に塗布し、その上からガラスを貼り合わせた。紫外線を照射せず、80℃で1時間加熱することにより、接着剤を硬化させ、評価用偏光板を作製した。
得られた評価用偏光板の180°剥離強度を、万能試験機(島津製作所社製、「EZグラフ」)を用いて、剥離速度5mm/分の条件で測定した。剥離強度が50N/25mm以上であった場合を「○」、20N/25mm以上50N/25mm未満であった場合を「△」、20N/25mm未満であった場合を「×」として接着性を評価した。
なお、実施例8で得られた表示デバイス用前面板貼り合わせ用接着剤については、熱ラジカル重合開始剤を用いなかったため、接着性2の評価を行わなかった。 (6) Adhesiveness 2 (after thermosetting)
Using the wire bar, the adhesive for bonding the front plate for display devices obtained in Examples 1 to 10 and Comparative Examples 1 to 7 was applied onto ITO-deposited PET (manufactured by Teijin Ltd.), and glass was applied from above. Were pasted together. The adhesive was cured by heating at 80 ° C. for 1 hour without irradiating with ultraviolet rays, and a polarizing plate for evaluation was produced.
The 180 ° peel strength of the obtained polarizing plate for evaluation was measured using a universal testing machine (manufactured by Shimadzu Corporation, “EZ Graph”) under the condition of a peel rate of 5 mm / min. The case where the peel strength was 50 N / 25 mm or more was evaluated as “◯”, the case where it was 20 N / 25 mm or more and less than 50 N / 25 mm as “Δ”, and the case where it was less than 20 N / 25 mm as “X”. did.
In addition, about the adhesive agent for front plate bonding for display devices obtained in Example 8, since the thermal radical polymerization initiator was not used, evaluation of adhesiveness 2 was not performed.
(ダム剤Aの調製)
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレート(ダイセルサイテック社製、「EBECRYL110」)5重量部と、フェノキシジエチレングリコールアクリレートのホモポリマー(ガラス転移温度-15℃、重量平均分子量3万)90重量部と、多官能ラジカル重合性化合物としてトリシクロデカンジメタノールジアクリレート(ダイセルサイテック社製、「IRR-214K」)5重量部と、光ラジカル重合開始剤として1-ヒドロキシシクロヘキシルフェニルケトン(BASF Japan社製、「イルガキュア184」)1重量部と、熱ラジカル重合開始剤としてベンゾイルパーオキサイド(日油社製、「ナイパーBW」)2重量部と、シランカップリング剤としてγ-グリシドキシプロピルメチルジエトキシシラン(信越シリコーン社製、「KBE-402」)1重量部とを、ホモディスパー型攪拌混合機(プライミクス社製、「ホモディスパーL型」)を用い、攪拌速度3000rpmで均一に攪拌混合してダム剤Aを得た。 (Production Example 1)
(Preparation of dam agent A)
As monofunctional radically polymerizable compounds, 5 parts by weight of phenoxydiethylene glycol acrylate (manufactured by Daicel Cytec, "EBECRYL110"), 90 parts by weight of a homopolymer of phenoxydiethylene glycol acrylate (glass transition temperature -15 ° C, weight average molecular weight 30,000), 5 parts by weight of tricyclodecane dimethanol diacrylate (manufactured by Daicel Cytec, “IRR-214K”) as a polyfunctional radical polymerizable compound, and 1-hydroxycyclohexyl phenyl ketone (manufactured by BASF Japan) as a photo radical polymerization initiator, "Irgacure 184") 1 part by weight, 2 parts by weight of benzoyl peroxide (manufactured by NOF Corporation, "NIPER BW") as a thermal radical polymerization initiator, and γ-glycidoxypropylmethyl as a
(ダム剤Bの調製)
フェノキシジエチレングリコールアクリレートの配合量を30重量部、フェノキシジエチレングリコールアクリレートのホモポリマーの配合量を65重量部に変更したこと以外は、製造例1と同様にしてダム剤Bを得た。 (Production Example 2)
(Preparation of dam agent B)
Dam agent B was obtained in the same manner as in Production Example 1 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 30 parts by weight and the blending amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 65 parts by weight.
(ダム剤Cの調製)
フェノキシジエチレングリコールアクリレートに代えてノニルフェニルテトラエチレングリコールアクリレート(共栄社化学社製、「ライトアクリレートNP-4EA」)5重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えてノニルフェニルテトラエチレングリコールアクリレートのホモポリマー(ガラス転移温度-25℃、重量平均分子量5万)90重量部を配合したこと以外は、製造例1と同様にしてダム剤Cを得た。 (Production Example 3)
(Preparation of dam agent C)
In place of phenoxydiethylene glycol acrylate, 5 parts by weight of nonylphenyl tetraethylene glycol acrylate (Kyoeisha Chemical Co., Ltd., “Light acrylate NP-4EA”) is blended, and instead of phenoxydiethylene glycol acrylate homopolymer, nonylphenyl tetraethylene glycol acrylate homopolymer is blended. Dam agent C was obtained in the same manner as in Production Example 1, except that 90 parts by weight of a polymer (glass transition temperature—25 ° C., weight average molecular weight 50,000) was blended.
(ダム剤Dの調製)
フェノキシジエチレングリコールアクリレートに代えて2-エチルヘキシルジエチレングリコールアクリレート(共栄社化学社製、「ライトアクリレートEHDG-A」)5重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えて2-エチルヘキシルジエチレングリコールアクリレートのホモポリマー(ガラス転移温度-30℃、重量平均分子量7万)90重量部を配合したこと以外は、製造例1と同様にしてダム剤Dを得た。 (Production Example 4)
(Preparation of dam agent D)
Instead of phenoxydiethylene glycol acrylate, 5 parts by weight of 2-ethylhexyl diethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “Light acrylate EHDG-A”) is blended, and instead of the homopolymer of phenoxydiethylene glycol acrylate, a homopolymer of 2-ethylhexyl diethylene glycol acrylate ( Dam agent D was obtained in the same manner as in Production Example 1 except that 90 parts by weight of glass transition temperature-30 ° C., weight average molecular weight 70,000) was blended.
(ダム剤Eの調製)
フェノキシジエチレングリコールアクリレートの配合量を1重量部に変更し、フェノキシジエチレングリコールアクリレートのホモポリマーの配合量を94重量部に変更したこと以外は、製造例1と同様にしてダム剤Eを得た。 (Production Example 5)
(Preparation of dam agent E)
Dam agent E was obtained in the same manner as in Production Example 1 except that the amount of phenoxydiethylene glycol acrylate was changed to 1 part by weight and the amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 94 parts by weight.
(フィル剤Aの調製)
単官能ラジカル重合性化合物としてフェノキシジエチレングリコールアクリレート(ダイセルサイテック社製、「EBECRYL110」)45重量部と、フェノキシジエチレングリコールアクリレートのホモポリマー(ガラス転移温度-15℃、重量平均分子量3万)50重量部と、多官能ラジカル重合性化合物としてトリシクロデカンジメタノールジアクリレート(ダイセルサイテック社製、「IRR-214K」)5重量部と、光ラジカル重合開始剤として1-ヒドロキシシクロヘキシルフェニルケトン(BASF Japan社製、「イルガキュア184」)1重量部と、熱ラジカル重合開始剤としてベンゾイルパーオキサイド(日油社製、「ナイパーBW」)2重量部と、シランカップリング剤としてγ-グリシドキシプロピルメチルジエトキシシラン(信越シリコーン社製、「KBE-402」)1重量部とを、ホモディスパー型攪拌混合機(プライミクス社製、「ホモディスパーL型」)を用い、攪拌速度3000rpmで均一に攪拌混合してフィル剤Aを得た。 (Production Example 6)
(Preparation of Fill Agent A)
As a monofunctional radical polymerizable compound, 45 parts by weight of phenoxydiethylene glycol acrylate (manufactured by Daicel Cytec, "EBECRYL110"), 50 parts by weight of a homopolymer of phenoxydiethylene glycol acrylate (glass transition temperature -15 ° C, weight average molecular weight 30,000), 5 parts by weight of tricyclodecane dimethanol diacrylate (manufactured by Daicel Cytec, “IRR-214K”) as a polyfunctional radical polymerizable compound, and 1-hydroxycyclohexyl phenyl ketone (manufactured by BASF Japan) as a photo radical polymerization initiator, "Irgacure 184") 1 part by weight, 2 parts by weight of benzoyl peroxide (manufactured by NOF Corporation, "NIPER BW") as a thermal radical polymerization initiator, and γ-glycidoxypropylmethyl as a
(フィル剤Bの調製)
フェノキシジエチレングリコールアクリレートの配合量を90重量部、フェノキシジエチレングリコールアクリレートのホモポリマーの配合量を5重量部に変更したこと以外は、製造例6と同様にしてフィル剤Bを得た。 (Production Example 7)
(Preparation of Fill Agent B)
Fill agent B was obtained in the same manner as in Production Example 6 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 90 parts by weight and the blending amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 5 parts by weight.
(フィル剤Cの調製)
フェノキシジエチレングリコールアクリレートに代えてノニルフェニルテトラエチレングリコールアクリレート(共栄社化学社製、「ライトアクリレートNP-4EA」)45重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えてノニルフェニルテトラエチレングリコールアクリレートのホモポリマー(ガラス転移温度-25℃、重量平均分子量5万)50重量部を配合したこと以外は、製造例6と同様にしてフィル剤Cを得た。 (Production Example 8)
(Preparation of fill agent C)
In place of phenoxydiethylene glycol acrylate, 45 parts by weight of nonylphenyl tetraethylene glycol acrylate (Kyoeisha Chemical Co., Ltd., “Light acrylate NP-4EA”) is blended, and in place of phenoxydiethylene glycol acrylate homopolymer, nonylphenyl tetraethylene glycol acrylate homopolymer is blended. Fill agent C was obtained in the same manner as in Production Example 6 except that 50 parts by weight of a polymer (glass transition temperature-25 ° C, weight average molecular weight 50,000) was blended.
(フィル剤Dの調製)
フェノキシジエチレングリコールアクリレートに代えて2-エチルヘキシルジエチレングリコールアクリレート(共栄社化学社製、「ライトアクリレートEHDG-A」)45重量部を配合し、フェノキシジエチレングリコールアクリレートのホモポリマーに代えて2-エチルヘキシルジエチレングリコールアクリレートのホモポリマー(ガラス転移温度-30℃、重量平均分子量7万)50重量部を配合したこと以外は、製造例6と同様にしてフィル剤Dを得た。 (Production Example 9)
(Preparation of fill agent D)
Instead of phenoxydiethylene glycol acrylate, 45 parts by weight of 2-ethylhexyl diethylene glycol acrylate (manufactured by Kyoeisha Chemical Co., Ltd., “Light Acrylate EHDG-A”) is blended, and instead of the homopolymer of phenoxydiethylene glycol acrylate, a homopolymer of 2-ethylhexyl diethylene glycol acrylate ( Fill agent D was obtained in the same manner as in Production Example 6 except that 50 parts by weight of glass transition temperature-30 ° C., weight average molecular weight 70,000) was blended.
(フィル剤Eの調製)
フェノキシジエチレングリコールアクリレートの配合量を35重量部に変更し、フェノキシジエチレングリコールアクリレートのホモポリマーの配合量を60重量部に変更したこと以外は、製造例6と同様にしてフィル剤Eを得た。 (Production Example 10)
(Preparation of fill agent E)
Fill agent E was obtained in the same manner as in Production Example 6 except that the blending amount of phenoxydiethylene glycol acrylate was changed to 35 parts by weight and the blending amount of the homopolymer of phenoxydiethylene glycol acrylate was changed to 60 parts by weight.
製造例1~10で得られたダム剤A~E、フィル剤A~Eについて以下の評価を行った。結果を表3に示した。 <Evaluation>
The following evaluation was performed on the dams A to E and the fillers A to E obtained in Production Examples 1 to 10. The results are shown in Table 3.
E型粘度計を用いて、25℃、2.5rpmの条件で、ダム剤A~E、フィル剤A~Eの粘度を測定した。 (1) Viscosity Using an E-type viscometer, the dam agents A to E and the fill agents A to E were measured under the conditions of 25 ° C. and 2.5 rpm.
ダム剤A~E、フィル剤A~Eを目視で観察し、透明な場合を「○」、不透明な場合を「×」としてモノマー成分とポリマー成分との相溶性を評価した。 (2) Compatibility dams A to E and fillers A to E were visually observed, and the compatibility between the monomer component and the polymer component was evaluated with “O” when transparent and “X” when opaque. .
ダム剤A~E、フィル剤A~Eに3000mJ/cm2の紫外線を照射して厚さ300μmのフィルムを作製し、波長405nmの光の透過率が90%以上の場合を「○」、90%未満の場合を「×」として透明性を評価した。 (3) Transparency of cured products Damping agents A to E and Filling agents A to E are irradiated with ultraviolet rays of 3000 mJ / cm 2 to produce a film having a thickness of 300 μm, and the transmittance of light having a wavelength of 405 nm is 90% or more. Transparency was evaluated with “◯” as the case of “x” and “x” as the case of less than 90%.
ダム剤A~E、フィル剤A~Eに3000mJ/cm2の紫外線を照射して厚さ300μmのフィルムを作製し、得られたフィルムを85℃、85%RHの恒温槽に500時間静置した。フィルムを恒温槽から取り出した後、目視にて確認し、白濁が見られず、透明であった場合を「○」、白濁がわずかに見られた場合を「△」、白濁がはっきりと見られた場合を「×」として硬化物の耐湿性を評価した。 (4) Moisture resistant dams A to E and fill agents A to E of the cured product were irradiated with 3000 mJ / cm 2 of ultraviolet rays to produce a film having a thickness of 300 μm, and the resulting film was 85 ° C., 85% RH For 500 hours. After removing the film from the thermostatic chamber, it is visually confirmed. When the film is transparent and transparent, “◯” is indicated. When the film is slightly observed, “△” is indicated. The moisture resistance of the cured product was evaluated as “x”.
ダム剤A~E、フィル剤A~Eを、ワイヤーバーを用いて、ITO蒸着PET(帝人社製)上に塗布し、その上からガラスを貼り合わせた。次いで、メタルハライドランプを用いて、3000mJ/cm2の紫外線を照射して接着剤を硬化させ、評価用偏光板を作製した。
得られた評価用偏光板の180°剥離強度を、万能試験機(島津製作所社製、「EZグラフ」)を用いて、剥離速度5mm/分の条件で測定した。剥離強度が50N/25mm以上であった場合を「○」、20N/25mm以上50N/25mm未満であった場合を「△」、20N/25mm未満であった場合を「×」として接着性を評価した。 (5) Adhesive dam agents A to E and fill agents A to E were applied onto ITO-deposited PET (manufactured by Teijin Ltd.) using a wire bar, and glass was laminated thereon. Next, using a metal halide lamp, the adhesive was cured by irradiating with 3000 mJ / cm 2 of ultraviolet rays to prepare a polarizing plate for evaluation.
The 180 ° peel strength of the obtained polarizing plate for evaluation was measured using a universal testing machine (manufactured by Shimadzu Corporation, “EZ Graph”) under the condition of a peel rate of 5 mm / min. The case where the peel strength was 50 N / 25 mm or more was evaluated as “◯”, the case where it was 20 N / 25 mm or more and less than 50 N / 25 mm as “Δ”, and the case where it was less than 20 N / 25 mm as “X”. did.
液晶パネルの周辺部にディスペンサー(武蔵エンジニアリング社製、「ショットマスター3」)を用いてダム剤Aを枠状に塗工した。次いで、液晶パネルのダム剤Aの枠内に、ディスペンサーを用いてフィル剤Aを塗工した。ダム剤A及びフィル剤Aを塗工した液晶パネルに前面板としてガラス板(無アルカリガラス、厚み0.7mm)を貼り合わせ、メタルハライドランプを用いて、3000mJ/cm2の紫外線を照射してダム剤A及びフィル剤Aを硬化させ、表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤及びフィル剤のはみ出しや流れ出しはなく、ダム剤とフィル剤との境界線も見えなかった。 (Example 11)
The dam agent A was applied in a frame shape to the periphery of the liquid crystal panel using a dispenser (manufactured by Musashi Engineering, “Shot Master 3”). Next, the fill agent A was applied in the frame of the dam agent A of the liquid crystal panel using a dispenser. A glass plate (non-alkali glass, thickness 0.7 mm) is bonded to the liquid crystal panel coated with the dam agent A and the fill agent A as a front plate and irradiated with 3000 mJ / cm 2 ultraviolet rays using a metal halide lamp. Agent A and Fill agent A were cured to produce a display device.
When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
フィル剤Aに代えてフィル剤Bを用いたこと以外は、実施例11と同様にして表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤及びフィル剤のはみ出しや流れ出しはなく、ダム剤とフィル剤との境界線も見えなかった。 Example 12
A display device was produced in the same manner as in Example 11 except that the filler B was used instead of the filler A.
When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
ダム剤Aに代えてダム剤Bを用いたこと以外は、実施例11と同様にして表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤及びフィル剤のはみ出しや流れ出しはなく、ダム剤とフィル剤との境界線も見えなかった。 (Example 13)
A display device was produced in the same manner as in Example 11 except that the dam agent B was used instead of the dam agent A.
When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
フィル剤Aに代えてフィル剤Bを用い、ダム剤Aに代えてダム剤Bを用いたこと以外は、実施例11と同様にして表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤及びフィル剤のはみ出しや流れ出しはなく、ダム剤とフィル剤との境界線も見えなかった。 (Example 14)
A display device was produced in the same manner as in Example 11 except that the filler B was used instead of the filler A and the dam agent B was used instead of the dam agent A.
When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
フィル剤Aに代えてフィル剤Cを用い、ダム剤Aに代えてダム剤Cを用いたこと以外は、実施例11と同様にして表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤及びフィル剤のはみ出しや流れ出しはなく、ダム剤とフィル剤との境界線も見えなかった。 (Example 15)
A display device was produced in the same manner as in Example 11 except that the fill agent C was used instead of the fill agent A, and the dam agent C was used instead of the dam agent A.
When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
フィル剤Aに代えてフィル剤Dを用い、ダム剤Aに代えてダム剤Dを用いたこと以外は、実施例11と同様にして表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤及びフィル剤のはみ出しや流れ出しはなく、ダム剤とフィル剤との境界線も見えなかった。 (Example 16)
A display device was produced in the same manner as in Example 11 except that the fill agent D was used instead of the fill agent A, and the dam agent D was used instead of the dam agent A.
When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
液晶パネルの周辺部にディスペンサー(武蔵エンジニアリング社製、「ショットマスター3」)を用いてダム剤Aを枠状に塗工した。次いで、液晶パネルのダム剤Aの枠内に、ディスペンサーを用いてフィル剤Aを塗工した。ダム剤A及びフィル剤Aを塗工した液晶パネルに、前面板として周囲に光を透過しない遮光部を設けたガラス板(無アルカリガラス、厚み0.7mm)を貼り合わせ、メタルハライドランプを用いて、3000mJ/cm2の紫外線を照射してダム剤A及びフィル剤Aを硬化させた。次いで、60℃で1時間加熱することにより、遮光部によって遮蔽されていた部分のダム剤A及びフィル剤Aを硬化させて、表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤及びフィル剤のはみ出しや流れ出しはなく、ダム剤とフィル剤との境界線も見えなかった。 (Example 17)
The dam agent A was applied in a frame shape to the periphery of the liquid crystal panel using a dispenser (manufactured by Musashi Engineering, “Shot Master 3”). Next, the fill agent A was applied in the frame of the dam agent A of the liquid crystal panel using a dispenser. A liquid crystal panel coated with the dam agent A and the fill agent A is bonded to a glass plate (non-alkali glass, thickness 0.7 mm) provided with a light-shielding portion that does not transmit light as a front plate, and a metal halide lamp is used. The dam agent A and the fill agent A were cured by irradiating ultraviolet rays of 3000 mJ / cm 2 . Next, by heating at 60 ° C. for 1 hour, the portion of the dam agent A and the fill agent A that were shielded by the light shielding portion were cured, and a display device was produced.
When the obtained display device was confirmed visually, the dam agent and the fill agent did not protrude or flow out, and the boundary line between the dam agent and the fill agent could not be seen.
ダム剤Aを用いず、ディスペンサーを用いてフィル剤Aを液晶パネルの前面板を貼り合わせる部分全体に塗布したこと以外は、実施例11と同様にして表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、液晶パネルと前面板との間からフィル剤Aのはみ出しが確認された。 (Reference Example 1)
A display device was produced in the same manner as in Example 11 except that the dam agent A was not used and the fill agent A was applied to the entire portion where the front plate of the liquid crystal panel was bonded using a dispenser.
When the obtained display device was confirmed visually, the protrusion of the fill agent A was confirmed between the liquid crystal panel and the front plate.
ダム剤Aに代えてダム剤Bを用い、フィル剤Aに代えてフィル剤Eを用いたこと以外は、実施例11と同様にして表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤が破れ、フィル剤のはみ出しが確認された。 (Reference Example 2)
A display device was produced in the same manner as in Example 11 except that the dam agent B was used instead of the dam agent A and the fill agent E was used instead of the fill agent A.
When the obtained display device was confirmed with the naked eye, the dam agent was broken and the protrusion of the fill agent was confirmed.
ダム剤Aに代えてダム剤Eを用い、フィル剤Aに代えてフィル剤Bを用いたこと以外は、実施例11と同様にして表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤及びフィル剤のはみ出しや流れ出しはなかったが、ダム剤とフィル剤との境界線のところでガラスの歪みが確認された。 (Reference Example 3)
A display device was produced in the same manner as in Example 11 except that the dam agent E was used instead of the dam agent A, and the fill agent B was used instead of the fill agent A.
When the obtained display device was visually confirmed, the dam agent and the fill agent did not protrude or flow out, but the distortion of the glass was confirmed at the boundary line between the dam agent and the fill agent.
ダム剤Aに代えてダム剤Cを用いたこと以外は、実施例11と同様にして表示デバイスを作製した。
得られた表示デバイスを目視にて確認したところ、ダム剤及びフィル剤のはみ出しや流れ出しはなかったが、ダム剤とフィル剤との境界線が確認できた。 (Reference Example 4)
A display device was produced in the same manner as in Example 11 except that the dam agent C was used instead of the dam agent A.
When the obtained display device was visually confirmed, the dam agent and the fill agent did not protrude or flow out, but the boundary line between the dam agent and the fill agent could be confirmed.
2 基材
3 表示デバイス用前面板貼り合わせ用接着剤
4 遮光部
5 光透過部
DESCRIPTION OF
Claims (9)
- 表示デバイスの基材と前面板との貼り合わせに用いる接着剤であって、
分子内に親水性基及び疎水性基を有する単官能ラジカル重合性化合物と、該単官能ラジカル重合性化合物のホモポリマーと、多官能ラジカル重合性化合物と、光ラジカル重合開始剤を含有する
ことを特徴とする表示デバイス用前面板貼り合わせ用接着剤。 An adhesive used for bonding the base material of the display device and the front plate,
A monofunctional radical polymerizable compound having a hydrophilic group and a hydrophobic group in the molecule, a homopolymer of the monofunctional radical polymerizable compound, a polyfunctional radical polymerizable compound, and a photo radical polymerization initiator. An adhesive for bonding a front plate for a display device. - 分子内に親水性基及び疎水性基を有する単官能ラジカル重合性化合物は、下記式(1)で表される化合物であることを特徴とする請求項1記載の表示デバイス用前面板貼り合わせ用接着剤。
- 熱ラジカル重合開始剤を含有することを特徴とする請求項1又は2記載の表示デバイス用前面板貼り合わせ用接着剤。 The adhesive for bonding a front plate for a display device according to claim 1, comprising a thermal radical polymerization initiator.
- 表示デバイスの基材と前面板との貼り合わせに用いる接着剤セットであって、
表示デバイスの周辺部において基材と前面板とを接着するダム剤と、前記ダム剤の内側において基材と前面板とを接着するフィル剤とからなり、
前記ダム剤及び前記フィル剤は、請求項1、2又は3記載の表示デバイス用前面板貼り合わせ用接着剤であって、それぞれ同じ単官能ラジカル重合性化合物、該単官能ラジカル重合性化合物のホモポリマー、多官能ラジカル重合性化合物、及び、光ラジカル重合開始剤を含有し、
前記ダム剤は、前記フィル剤よりも単官能ラジカル重合性化合物のホモポリマーの含有割合が高く、
E型粘度計を用いて、25℃、2.5rpmの条件で測定した前記ダム剤の粘度が、E型粘度計を用いて、25℃、2.5rpmの条件で測定した前記フィル剤の粘度の3~1万倍である
ことを特徴とする表示デバイス用前面板貼り合わせ用接着剤セット。 An adhesive set used for bonding the base material of the display device and the front plate,
It consists of a dam agent that adheres the base material and the front plate at the periphery of the display device, and a fill agent that adheres the base material and the front plate inside the dam agent,
The dam agent and the fill agent are adhesives for bonding a front plate for a display device according to claim 1, 2 or 3, and each of the same monofunctional radical polymerizable compound and homopolymer of the monofunctional radical polymerizable compound. Containing a polymer, a polyfunctional radical polymerizable compound, and a photo radical polymerization initiator,
The dam agent has a higher monopolymer radical polymerizable compound homopolymer content than the fill agent,
The viscosity of the dam agent measured under conditions of 25 ° C. and 2.5 rpm using an E-type viscometer is the viscosity of the fill agent measured under conditions of 25 ° C. and 2.5 rpm using an E-type viscometer. An adhesive set for laminating a front plate for a display device, characterized in that it is 30,000 to 10,000 times larger. - 基材と前面板とを、表示デバイス用前面板貼り合わせ用接着剤を用いて貼り合わせる表示デバイスの製造方法であって、
前記基材及び前記前面板の少なくとも一方に請求項1、2又は3記載の表示デバイス用前面板貼り合わせ用接着剤を塗布する工程と、
前記基材と前記前面板とを貼り合わせて、光を照射することにより前記表示デバイス用前面板貼り合わせ用接着剤を硬化させる工程とを含有する
ことを特徴とする表示デバイスの製造方法。 A method for producing a display device in which a base material and a front plate are bonded together using an adhesive for bonding a front plate for a display device,
Applying the adhesive for bonding a front plate for a display device according to claim 1, 2 or 3, to at least one of the base material and the front plate;
A method of manufacturing a display device, comprising: bonding the base material to the front plate and irradiating light to cure the display device front plate bonding adhesive. - 基材と前面板とを貼り合わせて、光を照射することにより表示デバイス用前面板貼り合わせ用接着剤を硬化させる工程において、光を照射するとともに、加熱することにより前記表示デバイス用前面板貼り合わせ用接着剤を硬化させることを特徴とする請求項5記載の表示デバイスの製造方法。 In the process of bonding the base material and the front plate and curing the adhesive for bonding the front plate for display device by irradiating light, the front plate for display device is bonded by irradiating light and heating. The method for manufacturing a display device according to claim 5, wherein the bonding adhesive is cured.
- 基材と前面板とを、表示デバイス用前面板貼り合わせ用接着剤を用いて貼り合わせる表示デバイスの製造方法であって、
基材及び前面板の少なくとも一方の周辺部にダム剤を枠状に塗工する工程と、
前記塗工したダム剤の枠内にフィル剤を塗工する工程と、
前記ダム剤及び前記フィル剤を介して、前記基材と前記前面板とを貼り合わせて、光を照射することにより、前記ダム剤及び前記フィル剤を硬化させる工程とを有し、
前記ダム剤及び前記フィル剤は、請求項4記載の表示デバイス用前面板貼り合わせ用接着剤セットのダム剤及びフィル剤である
ことを特徴とする表示デバイスの製造方法。 A method for producing a display device in which a base material and a front plate are bonded together using an adhesive for bonding a front plate for a display device,
A step of applying a dam agent in a frame shape to at least one peripheral portion of the base material and the front plate; and
Applying a fill agent within the frame of the applied dam agent;
The step of curing the dam agent and the fill agent by irradiating light by laminating the base material and the front plate through the dam agent and the fill agent,
The method for producing a display device, wherein the dam agent and the fill agent are the dam agent and the fill agent of the adhesive set for bonding a front plate for a display device according to claim 4. - ダム剤及びフィル剤を介して、前記基材と前記前面板とを貼り合わせて、光を照射して前記ダム剤及び前記フィル剤を硬化させる工程において、光を照射するとともに、加熱することにより前記ダム剤及び前記フィル剤を硬化させることを特徴とする請求項7記載の表示デバイスの製造方法。 In the step of laminating the base material and the front plate via a dam agent and a fill agent and irradiating light to cure the dam agent and the fill agent, by irradiating light and heating. The method for manufacturing a display device according to claim 7, wherein the dam agent and the fill agent are cured.
- 請求項1、2若しくは3記載の表示デバイス用前面板貼り合わせ用接着剤、又は、請求項4記載の表示デバイス用前面板貼り合わせ用接着剤セットを用いてなることを特徴とする表示デバイス。
A display device comprising the adhesive for bonding a front plate for a display device according to claim 1, 2, or 3, or the adhesive set for bonding a front plate for a display device according to claim 4.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201280021150.XA CN103502372B (en) | 2011-09-05 | 2012-09-05 | Adhesive for bonding front plate for display devices, adhesive set for bonding front plate for display devices, method for manufacturing display device, and display device |
JP2012544781A JP5244262B1 (en) | 2011-09-05 | 2012-09-05 | Display device front plate bonding adhesive, display device front plate bonding adhesive set, display device manufacturing method, and display device |
KR1020137025347A KR101436274B1 (en) | 2011-09-05 | 2012-09-05 | Adhesive for bonding front plate for display devices, adhesive set for bonding front plate for display devices, method for manufacturing display device, and display device |
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JP2011193007 | 2011-09-05 | ||
JP2011-193007 | 2011-09-05 | ||
JP2012-015505 | 2012-01-27 | ||
JP2012015505 | 2012-01-27 |
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WO2013035723A1 true WO2013035723A1 (en) | 2013-03-14 |
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PCT/JP2012/072565 WO2013035723A1 (en) | 2011-09-05 | 2012-09-05 | Adhesive for bonding front plate for display devices, adhesive set for bonding front plate for display devices, method for manufacturing display device, and display device |
Country Status (5)
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JP (1) | JP5244262B1 (en) |
KR (1) | KR101436274B1 (en) |
CN (1) | CN103502372B (en) |
TW (1) | TWI429726B (en) |
WO (1) | WO2013035723A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2014168173A1 (en) * | 2013-04-10 | 2014-10-16 | 電気化学工業株式会社 | Curable resin composition |
WO2014174775A1 (en) * | 2013-04-26 | 2014-10-30 | 昭和電工株式会社 | Bonding method and liquid loss inhibitor |
US20160251575A1 (en) * | 2013-10-22 | 2016-09-01 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
US9960389B1 (en) | 2017-05-05 | 2018-05-01 | 3M Innovative Properties Company | Polymeric films and display devices containing such films |
WO2023112873A1 (en) * | 2021-12-13 | 2023-06-22 | 積水化学工業株式会社 | Adhesive composition, adhesive for electronic components, and adhesive for portable electronic devices |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN105047831B (en) * | 2015-09-14 | 2017-06-13 | 上海天马有机发光显示技术有限公司 | A kind of packaging film, display device and its method for packing |
JP6710125B2 (en) * | 2016-08-04 | 2020-06-17 | 日本化薬株式会社 | Liquid crystal sealant and liquid crystal display cell using the same |
CN108468691B (en) * | 2018-03-07 | 2020-06-23 | 金龙机电(杭州)有限公司 | AB type glue laminating process of curved surface 3D touch screen or display screen |
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JP2007161909A (en) * | 2005-12-15 | 2007-06-28 | Soken Chem & Eng Co Ltd | Photopolymerizable adhesive composition and adhesive sheet using the same |
WO2008056787A1 (en) * | 2006-11-10 | 2008-05-15 | Asahi Glass Company, Limited | Method for manufacturing liquid crystal display and liquid crystal display |
JP2008174667A (en) * | 2007-01-19 | 2008-07-31 | Okura Ind Co Ltd | Active energy ray-curable adhesive composition and polarizing plate using the same |
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US8309003B2 (en) * | 2008-10-30 | 2012-11-13 | Lg Display Co., Ltd. | In-plane printing resin material and method of manufacturing liquid crystal display device using the same |
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- 2012-09-05 TW TW101132455A patent/TWI429726B/en not_active IP Right Cessation
- 2012-09-05 WO PCT/JP2012/072565 patent/WO2013035723A1/en active Application Filing
- 2012-09-05 KR KR1020137025347A patent/KR101436274B1/en active IP Right Grant
- 2012-09-05 CN CN201280021150.XA patent/CN103502372B/en not_active Expired - Fee Related
- 2012-09-05 JP JP2012544781A patent/JP5244262B1/en not_active Expired - Fee Related
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JP2007510041A (en) * | 2003-10-27 | 2007-04-19 | アドヒーシブズ・リサーチ・インコーポレイテッド | Poly (alkylene oxide) polymer pressure sensitive adhesive and tape formed therefrom |
JP2007161909A (en) * | 2005-12-15 | 2007-06-28 | Soken Chem & Eng Co Ltd | Photopolymerizable adhesive composition and adhesive sheet using the same |
WO2008056787A1 (en) * | 2006-11-10 | 2008-05-15 | Asahi Glass Company, Limited | Method for manufacturing liquid crystal display and liquid crystal display |
JP2008174667A (en) * | 2007-01-19 | 2008-07-31 | Okura Ind Co Ltd | Active energy ray-curable adhesive composition and polarizing plate using the same |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2014168173A1 (en) * | 2013-04-10 | 2014-10-16 | 電気化学工業株式会社 | Curable resin composition |
JPWO2014168173A1 (en) * | 2013-04-10 | 2017-02-16 | デンカ株式会社 | Curable resin composition |
WO2014174775A1 (en) * | 2013-04-26 | 2014-10-30 | 昭和電工株式会社 | Bonding method and liquid loss inhibitor |
US20160251575A1 (en) * | 2013-10-22 | 2016-09-01 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
US9960389B1 (en) | 2017-05-05 | 2018-05-01 | 3M Innovative Properties Company | Polymeric films and display devices containing such films |
US10797269B2 (en) | 2017-05-05 | 2020-10-06 | 3M Innovative Properties Company | Polymeric films and display devices containing such films |
US11472909B2 (en) | 2017-05-05 | 2022-10-18 | 3M Innovative Properties Company | Polymeric films and display devices containing such films |
WO2023112873A1 (en) * | 2021-12-13 | 2023-06-22 | 積水化学工業株式会社 | Adhesive composition, adhesive for electronic components, and adhesive for portable electronic devices |
Also Published As
Publication number | Publication date |
---|---|
JP5244262B1 (en) | 2013-07-24 |
JPWO2013035723A1 (en) | 2015-03-23 |
KR101436274B1 (en) | 2014-08-29 |
CN103502372B (en) | 2014-08-27 |
TWI429726B (en) | 2014-03-11 |
KR20130126718A (en) | 2013-11-20 |
CN103502372A (en) | 2014-01-08 |
TW201319200A (en) | 2013-05-16 |
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