WO2015064410A1 - 有機ｅｌ表示素子用封止剤 - Google Patents
有機ｅｌ表示素子用封止剤 Download PDFInfo
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- WO2015064410A1 WO2015064410A1 PCT/JP2014/077821 JP2014077821W WO2015064410A1 WO 2015064410 A1 WO2015064410 A1 WO 2015064410A1 JP 2014077821 W JP2014077821 W JP 2014077821W WO 2015064410 A1 WO2015064410 A1 WO 2015064410A1
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- 238000007789 sealing Methods 0.000 title claims abstract description 46
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 53
- 229920005989 resin Polymers 0.000 claims abstract description 41
- 239000011347 resin Substances 0.000 claims abstract description 41
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 21
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 15
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 11
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000002091 cationic group Chemical group 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- -1 2,4-cyclopentadien-1-yl Chemical group 0.000 description 45
- 239000011248 coating agent Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 15
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 14
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 14
- 239000000565 sealant Substances 0.000 description 12
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- 239000002253 acid Substances 0.000 description 9
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- 230000000052 comparative effect Effects 0.000 description 7
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- UCBQKJQXUPVHFJ-UHFFFAOYSA-N 1-cyclopenta-2,4-dien-1-yl-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1C1C=CC=C1 UCBQKJQXUPVHFJ-UHFFFAOYSA-N 0.000 description 4
- PFHLXMMCWCWAMA-UHFFFAOYSA-N [4-(4-diphenylsulfoniophenyl)sulfanylphenyl]-diphenylsulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC(C=C1)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 PFHLXMMCWCWAMA-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 235000010216 calcium carbonate Nutrition 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- HYVNJCOHGOONJK-UHFFFAOYSA-N dibenzyl-methyl-phenylazanium Chemical compound C=1C=CC=CC=1C[N+](C=1C=CC=CC=1)(C)CC1=CC=CC=C1 HYVNJCOHGOONJK-UHFFFAOYSA-N 0.000 description 3
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- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- 102100033806 Alpha-protein kinase 3 Human genes 0.000 description 2
- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 2
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- 229910018286 SbF 6 Inorganic materials 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
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- 229910000278 bentonite Inorganic materials 0.000 description 2
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- ONRGBXGMVZEZLY-UHFFFAOYSA-N dimethyl-[(4-methylphenyl)methyl]-phenylazanium Chemical compound C1=CC(C)=CC=C1C[N+](C)(C)C1=CC=CC=C1 ONRGBXGMVZEZLY-UHFFFAOYSA-N 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
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- 150000004714 phosphonium salts Chemical class 0.000 description 2
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- 238000007665 sagging Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- VLTYTTRXESKBKI-UHFFFAOYSA-N (2,4-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VLTYTTRXESKBKI-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- NQEJEMZJOBCYOD-UHFFFAOYSA-N (4-methoxyphenyl)methyl-dimethyl-phenylazanium Chemical compound C1=CC(OC)=CC=C1C[N+](C)(C)C1=CC=CC=C1 NQEJEMZJOBCYOD-UHFFFAOYSA-N 0.000 description 1
- QKAIFCSOWIMRJG-UHFFFAOYSA-N (4-methylphenyl)-(4-propan-2-ylphenyl)iodanium Chemical compound C1=CC(C(C)C)=CC=C1[I+]C1=CC=C(C)C=C1 QKAIFCSOWIMRJG-UHFFFAOYSA-N 0.000 description 1
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 1
- USGYMDAUQBQWFU-UHFFFAOYSA-N 1,2,5,6-diepoxycyclooctane Chemical compound C1CC2OC2CCC2OC12 USGYMDAUQBQWFU-UHFFFAOYSA-N 0.000 description 1
- QLGYTJLZFZUDFL-UHFFFAOYSA-N 1,3-bis[1-(1h-imidazol-2-yl)propyl]urea Chemical compound N=1C=CNC=1C(CC)NC(=O)NC(CC)C1=NC=CN1 QLGYTJLZFZUDFL-UHFFFAOYSA-N 0.000 description 1
- VSHKLLPSERFSRJ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)pyridin-1-ium-2-carbonitrile Chemical compound N#CC1=CC=CC=[N+]1CC1=CC=CC2=CC=CC=C12 VSHKLLPSERFSRJ-UHFFFAOYSA-N 0.000 description 1
- OBSKXJSZGYXFFB-UHFFFAOYSA-N 1-benzylpyridin-1-ium-2-carbonitrile Chemical compound N#CC1=CC=CC=[N+]1CC1=CC=CC=C1 OBSKXJSZGYXFFB-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 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 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- VDAIJDKQXDCJSI-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethylurea Chemical compound CC1=NC=CN1CCNC(N)=O VDAIJDKQXDCJSI-UHFFFAOYSA-N 0.000 description 1
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- TZLVUWBGUNVFES-UHFFFAOYSA-N 2-ethyl-5-methylpyrazol-3-amine Chemical compound CCN1N=C(C)C=C1N TZLVUWBGUNVFES-UHFFFAOYSA-N 0.000 description 1
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 1
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
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- LNKMXDMYWXREMQ-UHFFFAOYSA-M COC(C=C1)=CC=C1[S+](C(C=C1)=CC=C1OC)C(C=C1)=CC=C1OC.[F-].F.F.F.F.F.[AsH3] Chemical compound COC(C=C1)=CC=C1[S+](C(C=C1)=CC=C1OC)C(C=C1)=CC=C1OC.[F-].F.F.F.F.F.[AsH3] LNKMXDMYWXREMQ-UHFFFAOYSA-M 0.000 description 1
- GMXOYEFGMAXIIU-UHFFFAOYSA-N C[N+](CC1=CC(=C(C=C1)C)C)(C1=CC=CC=C1)C Chemical compound C[N+](CC1=CC(=C(C=C1)C)C)(C1=CC=CC=C1)C GMXOYEFGMAXIIU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
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- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
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- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 1
- GROOQLAYIIFIBG-UHFFFAOYSA-N [B+3].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [B+3].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 GROOQLAYIIFIBG-UHFFFAOYSA-N 0.000 description 1
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- BFVANNVEMACRTA-UHFFFAOYSA-N [Sb+3].CCCC[P+](CCCC)(CCCC)CCCC Chemical compound [Sb+3].CCCC[P+](CCCC)(CCCC)CCCC BFVANNVEMACRTA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 239000012965 benzophenone Substances 0.000 description 1
- AENNXXRRACDJAY-UHFFFAOYSA-N bis(2-dodecylphenyl)iodanium Chemical compound CCCCCCCCCCCCC1=CC=CC=C1[I+]C1=CC=CC=C1CCCCCCCCCCCC AENNXXRRACDJAY-UHFFFAOYSA-N 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
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- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
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- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
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- 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
- URQUNWYOBNUYJQ-UHFFFAOYSA-N diazonaphthoquinone Chemical compound C1=CC=C2C(=O)C(=[N]=[N])C=CC2=C1 URQUNWYOBNUYJQ-UHFFFAOYSA-N 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance 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
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- BLGWXSOTAXXXDE-UHFFFAOYSA-N n'-[1-(1h-imidazol-2-yl)propyl]hexanediamide Chemical compound NC(=O)CCCCC(=O)NC(CC)C1=NC=CN1 BLGWXSOTAXXXDE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- HMKGBOLFVMRQRP-UHFFFAOYSA-N tribenzyl(phenyl)azanium Chemical compound C=1C=CC=CC=1C[N+](C=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 HMKGBOLFVMRQRP-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 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
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/06—Triglycidylisocyanurates
-
- 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
Definitions
- the present invention relates to a sealant for organic EL display elements that can suppress the generation of outgas and is excellent in applicability.
- organic electroluminescence (organic EL) display elements and organic thin film solar cell elements have been advanced.
- the organic thin film element can be easily produced by vacuum deposition, solution coating, or the like, and thus has excellent productivity.
- the organic EL display element has a thin film structure in which an organic light emitting material layer is sandwiched between a pair of electrodes facing each other. When electrons are injected from one electrode into the organic light emitting material layer and holes are injected from the other electrode, electrons and holes are combined in the organic light emitting material layer to perform self-light emission. Compared with a liquid crystal display element or the like that requires a backlight, the visibility is better, the thickness can be reduced, and direct current low voltage driving is possible.
- an organic EL display element has a problem that when the organic light emitting material layer and the electrode are exposed to the outside air, the light emission characteristics thereof are rapidly deteriorated and the life is shortened. Therefore, for the purpose of improving the stability and durability of the organic EL display element, in the organic EL display element, a sealing technique for shielding the organic light emitting material layer and the electrode from moisture and oxygen in the atmosphere is indispensable. Yes.
- Patent Document 1 discloses a method of sealing a top emission organic EL display element by filling a curable adhesive between organic EL display element substrates and irradiating light.
- a display element such as an organic EL display element is sealed using a curable adhesive in this way, outgas is generated during light irradiation or heating and fills the element, accelerating deterioration of the element. There was a problem that sometimes.
- An object of this invention is to provide the sealing agent for organic EL display elements which can suppress generation
- the present invention is an organic EL display element sealing agent containing a cationic curable resin and a cationic polymerization initiator, wherein the cationic curable resin has an epoxy group or an oxetanyl group, and an epoxy group.
- an organic EL display element sealing agent that does not have an ether bond and an ester bond other than those contained in the oxetanyl group, and was measured using an E-type viscometer at 25 ° C. and 1 to 100 rpm.
- This is a sealing agent for organic EL display elements having an overall viscosity of 80 to 5000 mPa ⁇ s.
- the present invention is described in detail below.
- the present inventors considered that the cause of outgas generation when a curable adhesive is used for sealing an organic EL display element is an ether bond or an ester bond contained in the curable resin used. That is, it was considered that the outgas was generated by the decomposition of the ether bond or the ester bond contained in the curable resin with an acid derived from an initiator or the like. For this reason, the use of a curable resin that does not contain an ether bond or an ester bond that causes outgassing was studied. Depending on the type of curable resin to be used, the obtained sealing agent for organic EL display elements was applied. It may become inferior.
- the present inventors have specified a cationic curable resin having an epoxy group or an oxetanyl group as the curable resin and not having an ether bond and an ester bond other than those contained in the epoxy group or oxetanyl group. As a result, it was found that outgassing can be suppressed and a sealing agent for organic EL display elements having excellent coating properties can be obtained, and the present invention has been completed.
- the sealing agent for organic EL display elements of the present invention contains a cationic curable resin.
- the cationic curable resin has an epoxy group or an oxetanyl group and does not have an ether bond and an ester bond other than those contained in the epoxy group or the oxetanyl group (hereinafter referred to as “cationic curing according to the present invention”). Also referred to as “resin”.
- the cation curable resin preferably contains a compound represented by the following formula (1) and / or a compound represented by the following formula (2), since generation of outgas can be effectively suppressed. From the viewpoint of curability and curing, it is more preferable to contain a compound represented by the following formula (1).
- R 1 to R 18 are a hydrogen atom, a halogen atom, or a hydrocarbon group that may contain an oxygen atom or a halogen atom, and may be the same or different. Also good.
- R 19 to R 21 are linear or branched alkylene groups having 2 to 10 carbon atoms, which may be the same or different.
- E 1 to E 3 each independently represents an organic group represented by the following formula (3-1) or the following formula (3-2).
- R 22 represents a hydrogen atom or a methyl group.
- the said cationic curable resin shows favorable cationic curability, it is preferable to contain the compound represented by following formula (4) as a compound represented by the said Formula (1).
- the cationic curable resin contains a compound represented by the following formula (5) as a compound represented by the above formula (2) because it exhibits good cationic curability and the cured product exhibits a high glass transition temperature. It is preferable to do.
- the cationic curable resin can easily adjust the curing retardation and viscosity of the obtained sealing agent for organic EL display elements, it is represented by the compound represented by the above formula (1) and the above formula (2). It is preferred to contain both compounds. Further, by containing the compound represented by the above formula (2) in addition to the compound represented by the above formula (1), it is possible to suppress the volatilization of the raw material until the curing reaction occurs, and to obtain the organic Application shape stability of the sealing agent for EL display elements is improved.
- the cationic curable resin contains both the compound represented by the formula (1) and the compound represented by the formula (2), it is represented by the compound represented by the formula (1) and the formula (2).
- cationic curable resin examples include dicyclopentadiene diepoxide and 1,2,5,6-diepoxycyclooctane.
- the sealing agent for organic EL display elements of the present invention increases the dispersibility of the filler described later and moderately adjusts the viscosity of the resulting sealing agent for organic EL display elements within a range that does not impair the object of the present invention.
- other cationic curable resins having an ether bond or an ester bond other than those contained in the epoxy group or oxetanyl group may be contained.
- the other cationic curable resin is at least one selected from the group consisting of an epoxy resin having a bisphenol skeleton, an epoxy resin having a novolac skeleton, an epoxy resin having a naphthalene skeleton, and an epoxy resin having a dicyclopentadiene skeleton.
- a kind of epoxy resin is preferable, an epoxy resin having a bisphenol skeleton is more preferable, and a bisphenol F-type epoxy resin is more preferable.
- the content of the cation curable resin according to the present invention is preferably 10 parts by weight and preferably 80 parts by weight with respect to 100 parts by weight of the whole cation curable resin. It is.
- the content of the cationic curable resin according to the present invention is less than 10 parts by weight or more than 80 parts by weight, the obtained sealing agent for organic EL display elements may be inferior in applicability.
- the more preferable lower limit of the content of the cationic curable resin according to the present invention is 20 parts by weight, and the more preferable upper limit is 70 parts by weight.
- the sealing agent for organic EL display elements of the present invention contains a cationic polymerization initiator.
- the cationic polymerization initiator include a photocationic polymerization initiator that generates a protonic acid or a Lewis acid by light irradiation, and a thermal cationic polymerization initiator that generates a protonic acid or a Lewis acid by heating. These are not particularly limited as long as they are ionic acid generating types or nonionic acid generating types.
- the photocationic polymerization initiator is not particularly limited as long as it generates a protonic acid or a Lewis acid by light irradiation, and may be an ionic photoacid generating type or a nonionic photoacid generating type. May be.
- Examples of the ionic photoacid-generating photocationic polymerization initiator include those having a cation moiety of aromatic sulfonium, aromatic iodonium, aromatic diazonium, aromatic ammonium, or (2,4-cyclopentadien-1-yl). ) ((1-methylethyl) benzene) -Fe cation, and the anion portion is BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , or (BX 4 ) ⁇ (where X is at least two or more fluorine atoms) Or an onium salt composed of a phenyl group substituted with a trifluoromethyl group).
- aromatic sulfonium salt examples include bis (4- (diphenylsulfonio) phenyl) sulfide bishexafluorophosphate, bis (4- (diphenylsulfonio) phenyl) sulfide bishexafluoroantimonate, and bis (4- ( Diphenylsulfonio) phenyl) sulfide bistetrafluoroborate, bis (4- (diphenylsulfonio) phenyl) sulfide tetrakis (pentafluorophenyl) borate, diphenyl-4- (phenylthio) phenylsulfonium hexafluorophosphate, diphenyl-4- ( Phenylthio) phenylsulfonium hexafluoroantimonate, diphenyl-4- (phenylthio) phenylsulfonium tetraflu
- aromatic iodonium salt examples include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis (pentafluorophenyl) borate, bis (dodecylphenyl) iodonium hexafluorophosphate, bis (Dodecylphenyl) iodonium hexafluoroantimonate, bis (dodecylphenyl) iodonium tetrafluoroborate, bis (dodecylphenyl) iodonium tetrakis (pentafluorophenyl) borate, 4-methylphenyl-4- (1-methylethyl) phenyliodonium hexa Fluorophosphate, 4-methylphenyl-4- (1-methylethy
- aromatic diazonium salt examples include phenyldiazonium hexafluorophosphate, phenyldiazonium hexafluoroantimonate, phenyldiazonium tetrafluoroborate, and phenyldiazonium tetrakis (pentafluorophenyl) borate.
- aromatic ammonium salt examples include 1-benzyl-2-cyanopyridinium hexafluorophosphate, 1-benzyl-2-cyanopyridinium hexafluoroantimonate, 1-benzyl-2-cyanopyridinium tetrafluoroborate, 1-benzyl -2-Cyanopyridinium tetrakis (pentafluorophenyl) borate, 1- (naphthylmethyl) -2-cyanopyridinium hexafluorophosphate, 1- (naphthylmethyl) -2-cyanopyridinium hexafluoroantimonate, 1- (naphthylmethyl)
- Examples include -2-cyanopyridinium tetrafluoroborate and 1- (naphthylmethyl) -2-cyanopyridinium tetrakis (pentafluorophenyl) borate.
- Examples of the (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene) -Fe salt include (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene.
- nonionic photoacid-generating photocationic polymerization initiator examples include nitrobenzyl ester, sulfonic acid derivative, phosphoric ester, phenolsulfonic acid ester, diazonaphthoquinone, N-hydroxyimide sulfonate and the like.
- photocationic polymerization initiators examples include, for example, DTS-200 (manufactured by Midori Chemical Co., Ltd.), UVI6990, UVI6974 (all manufactured by Union Carbide), SP-150, SP-170 (all ADEKA), FC-508, FC-512 (all from 3M), IRGACURE 261, IRGACURE 290 (all from BASF Japan), PI 2074 (from Rhodia), and the like.
- thermal cationic polymerization initiator examples include BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , or (BX 4 ) ⁇ (wherein X is substituted with at least two fluorine or trifluoromethyl groups.
- a sulfonium salt, a phosphonium salt, a quaternary ammonium salt, a diazonium salt, an iodonium salt, and the like are preferred.
- sulfonium salts include triphenylsulfonium boron tetrafluoride, triphenylsulfonium hexafluoride antimony, triphenylsulfonium hexafluoride arsenic, tri (4-methoxyphenyl) sulfonium hexafluoride arsenic, and diphenyl (4-phenylthiophenyl). ) Sulfonium arsenic hexafluoride and the like.
- the phosphonium salt include ethyltriphenylphosphonium antimony hexafluoride and tetrabutylphosphonium antimony hexafluoride.
- Examples of the quaternary ammonium salt include dimethylphenyl (4-methoxybenzyl) ammonium hexafluorophosphate, dimethylphenyl (4-methoxybenzyl) ammonium hexafluoroantimonate, dimethylphenyl (4-methoxybenzyl) ammonium tetrakis (penta).
- Fluorophenyl) borate dimethylphenyl (4-methylbenzyl) ammonium hexafluorohexafluorophosphate, dimethylphenyl (4-methylbenzyl) ammonium hexafluoroantimonate, dimethylphenyl (4-methylbenzyl) ammonium hexafluorotetrakis (pentafluorophenyl) ) Borate, methylphenyldibenzylammonium, methylphenyldibenzylammonium hexaf Oroantimonate hexafluorophosphate, methylphenyldibenzylammonium trakis (pentafluorophenyl) borate, phenyltribenzylammonium tetrakis (pentafluorophenyl) borate, dimethylphenyl (3,4-dimethylbenzyl) ammonium tetrakis (pentafluorophenyl) Borate
- thermal cationic polymerization initiators examples include, for example, Adeka Opton CP-66, Adeka Opton CP-77 (both manufactured by ADEKA), and thermal cations having not only thermal activity but also photoactivity.
- Polymerization initiators such as Sun-Aid SI-60, Sun-Aid SI-80, Sun-Aid SI-100, Sun-Aid SI-110, Sun-Aid SI-180 (all manufactured by Sanshin Chemical Industry Co., Ltd.), CXC-1612, CXC-1738, CXC -1821 (all manufactured by King Industries).
- the content of the cationic polymerization initiator is preferably 0.1 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the cationic curable resin. If the content of the cationic polymerization initiator is less than 0.1 parts by weight, the cationic polymerization may not proceed sufficiently, or the curing reaction may become too slow. When the content of the cationic polymerization initiator exceeds 10 parts by weight, the curing reaction of the resulting organic EL display element sealant becomes too fast, resulting in a decrease in workability or the resulting organic EL display element seal. The cured product of the stopper may become uneven.
- the minimum with more preferable content of the said cationic polymerization initiator is 0.5 weight part, and a more preferable upper limit is 5 weight part.
- the sealing agent for organic EL display elements of the present invention may contain a sensitizer.
- the sensitizer has a role of further improving the polymerization initiation efficiency of the cationic polymerization initiator and further promoting the curing reaction of the sealant for organic EL display elements of the present invention.
- sensitizer examples include thioxanthone compounds such as 2,4-diethylthioxanthone, 2,2-dimethoxy-1,2-diphenylethane-1-one, benzophenone, 2,4-dichlorobenzophenone, o- Examples include methyl benzoylbenzoate, 4,4′-bis (dimethylamino) benzophenone, 4-benzoyl-4′methyldiphenyl sulfide, and the like.
- thioxanthone compounds such as 2,4-diethylthioxanthone, 2,2-dimethoxy-1,2-diphenylethane-1-one, benzophenone, 2,4-dichlorobenzophenone, o- Examples include methyl benzoylbenzoate, 4,4′-bis (dimethylamino) benzophenone, 4-benzoyl-4′methyldiphenyl sulfide, and the like.
- the content of the sensitizer is preferably 0.05 parts by weight and preferably 3 parts by weight with respect to 100 parts by weight of the cationic curable resin.
- the sensitizing effect may not be sufficiently obtained.
- the content of the sensitizer exceeds 3 parts by weight, absorption may be excessively increased and light may not be transmitted to the deep part.
- the minimum with more preferable content of the said sensitizer is 0.1 weight part, and a more preferable upper limit is 1 weight part.
- the sealing agent for organic EL display elements of the present invention preferably contains a filler for the purpose of improving the moisture resistance of the cured product.
- a filler for the purpose of improving the moisture resistance of the cured product.
- the compound represented by the above formula (1) having a low viscosity is used as the cationic curable resin according to the present invention, a large amount of filler can be blended without deteriorating the coating property.
- the filler examples include talc, asbestos, silica, mica, diatomaceous earth, smectite, bentonite, calcium carbonate, magnesium carbonate, alumina, montmorillonite, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, and magnesium hydroxide.
- Inorganic fillers such as aluminum hydroxide, silicon nitride, barium sulfate, gypsum, calcium silicate, glass beads, sericite activated clay, bentonite, aluminum nitride, polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, acrylic polymer fine particles, etc.
- the preferred lower limit of the content of the filler is 10 parts by weight and the preferred upper limit is 80 parts by weight with respect to 100 parts by weight of the cationic curable resin. If the content of the filler is less than 10 parts by weight, the effect of improving moisture resistance may not be sufficiently exhibited. When content of the said filler exceeds 80 weight part, the viscosity of the sealing agent for organic EL display elements obtained will become high too much, and applicability
- the minimum with more preferable content of the said filler is 15 weight part, and a more preferable upper limit is 70 weight part.
- the sealing agent for organic EL display elements of the present invention may contain a silane coupling agent.
- the said silane coupling agent has a role which improves the adhesiveness of the sealing agent for organic EL display elements of this invention, a board
- silane coupling agent examples include 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, and the like. These silane coupling agents may be used independently and 2 or more types may be used together.
- the content of the silane coupling agent is preferably 0.1 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the cation curable resin.
- the content of the silane coupling agent is less than 0.1 parts by weight, the effect of improving the adhesiveness of the obtained sealing agent for organic EL display elements may not be sufficiently exhibited.
- content of the said silane coupling agent exceeds 10 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, and a more preferable upper limit is 5 weight part.
- the sealing agent for organic EL display elements of the present invention may further contain a thermosetting agent as long as the object of the present invention is not impaired. By containing the said thermosetting agent, thermosetting property can be provided to the sealing agent for organic EL display elements of this invention.
- thermosetting agent is not particularly limited, and examples thereof include hydrazide compounds, imidazole derivatives, acid anhydrides, dicyandiamides, guanidine derivatives, modified aliphatic polyamines, addition products of various amines and epoxy resins, and the like.
- hydrazide compound include 1,3-bis [hydrazinocarbonoethyl-5-isopropylhydantoin] and the like.
- imidazole derivative examples include 1-cyanoethyl-2-phenylimidazole, N- [2- (2-methyl-1-imidazolyl) ethyl] urea, 2,4-diamino-6- [2′-methylimidazolyl- (1 ′)]-ethyl-s-triazine, N, N′-bis (2-methyl-1-imidazolylethyl) urea, N, N ′-(2-methyl-1-imidazolylethyl) -adipamide, 2- Examples include phenyl-4-methyl-5-hydroxymethylimidazole and 2-phenyl-4,5-dihydroxymethylimidazole.
- acid anhydride examples include tetrahydrophthalic anhydride, ethylene glycol bis (anhydro trimellitate), and the like. These thermosetting agents may be used alone or in combination of two or more.
- the content of the thermosetting agent is preferably 0.5 parts by weight and preferably 30 parts by weight with respect to 100 parts by weight of the cationic curable resin.
- the content of the thermosetting agent is less than 0.5 parts by weight, sufficient thermosetting property may not be imparted to the obtained sealing agent for organic EL display elements.
- the content of the thermosetting agent exceeds 30 parts by weight, the storage stability of the obtained sealant for organic EL display elements becomes insufficient, or the cured product of the obtained sealant for organic EL display elements. Moisture resistance may deteriorate.
- the minimum with more preferable content of the said thermosetting agent is 1 weight part, and a more preferable upper limit is 15 weight part.
- the sealing agent for organic EL display elements of the present invention may contain a surface modifier as long as the object of the present invention is not impaired.
- a surface modifier By containing the surface modifier, the flatness of the coating film can be imparted to the organic EL display element sealant of the present invention.
- the surface modifier include surfactants and leveling agents.
- surfactant and the leveling agent examples include silicon-based, acrylic-based, and fluorine-based ones.
- examples of commercially available surfactants and leveling agents include BYK-345 (manufactured by BYK Japan), BYK-340 (manufactured by BYK Japan), Surflon S-611 (AGC Seimi Chemical). Etc.).
- the encapsulant for organic EL display elements of the present invention reacts with the acid generated in the encapsulant for organic EL display elements in order to improve the durability of the element electrode within a range not impairing the object of the present invention.
- a compound or an ion exchange resin may be contained.
- Examples of the compound that reacts with the generated acid include substances that neutralize the acid, for example, alkali metal carbonates or bicarbonates, or alkaline earth metal carbonates or bicarbonates.
- alkali metal carbonates or bicarbonates or alkaline earth metal carbonates or bicarbonates.
- calcium carbonate, calcium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate and the like are used.
- any of a cation exchange type, an anion exchange type, and a both ion exchange type can be used, and in particular, a cation exchange type or a both ion exchange type capable of adsorbing chloride ions. Is preferred.
- the sealing agent for organic EL display elements of this invention is a range which does not inhibit the objective of this invention, and is a hardening retarder, a reinforcing agent, a softener, a plasticizer, a viscosity modifier, and an ultraviolet absorber as needed. Further, various known additives such as antioxidants may be contained.
- Examples of the method for producing the sealing agent for organic EL display elements of the present invention include a cation curable resin using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three roll. And a method of mixing a cationic polymerization initiator and an additive to be added as necessary.
- the sealant for organic EL display elements of the present invention has an overall viscosity lower limit of 80 mPa ⁇ s and an upper limit of 5000 mPa ⁇ s measured using an E-type viscometer at 25 ° C. and 1 to 100 rpm.
- the viscosity is less than 80 mPa ⁇ s
- the obtained sealing agent for organic EL display elements is inferior in applicability and shape stability after application, composition unevenness occurs, and the cured product becomes transparent. It becomes inferior.
- the sealing agent for organic EL display elements obtained will be inferior to applicability
- the preferable lower limit of the viscosity is 150 mPa ⁇ s
- the preferable upper limit is 3000 mPa ⁇ s
- the more preferable lower limit is 200 mPa ⁇ s
- the more preferable upper limit is 1000 mPa ⁇ s.
- the viscosity can be measured, for example, with a CP1 type cone plate using VISCOMETER TV-22 (manufactured by Toki Sangyo Co., Ltd.) as an E type viscometer.
- the viscosity when measuring using an E-type viscometer, when the viscosity is 1000 mPa ⁇ s or more and less than 5000 mPa ⁇ s, it is measured under the condition of 1 rpm, and when the viscosity is 500 mPa ⁇ s or more and less than 1000 mPa ⁇ s, it is 5 rpm. When the viscosity is 200 mPa ⁇ s or more and less than 500 mPa ⁇ s, the measurement is performed under the condition of 10 rpm.
- the measurement is performed under the condition of 20 rpm, and the viscosity is 50 mPa ⁇ s. -When it becomes less than s, it is preferable to measure on the conditions of 100 rpm.
- Example 1 As the cationic curable resin, 50 parts by weight of a compound represented by the above formula (4) (manufactured by Daicel, “Celoxide 8000”) and a compound represented by the above formula (5) (manufactured by Nissan Chemical Co., Ltd., “TEPIC-VL”). ”) 50 parts by weight and 1 part by weight of an aromatic sulfonium salt (manufactured by Midori Chemical Co.,“ DTS-200 ”) as a photocationic polymerization initiator are mixed and heated to 80 ° C., and then stirred and mixed (Sinky Corporation). Manufactured by “AR-250”) and uniformly mixed at a stirring speed of 3000 rpm to prepare an organic EL display element sealing agent.
- a compound represented by the above formula (4) manufactured by Daicel, “Celoxide 8000”
- a compound represented by the above formula (5) manufactured by Nissan Chemical Co., Ltd., “TEPIC-VL”.
- Examples 2 to 7, Comparative Examples 1 to 6 Each material described in Table 1 was stirred and mixed in the same manner as in Example 1 in accordance with the blending ratio described in Table 1 to prepare an organic EL display element sealant.
- the organic EL display element sealants obtained in Examples 4 to 6 and Comparative Examples 2 and 5 were cured by heating at 100 ° C. for 30 minutes without irradiation with ultraviolet rays.
- the change in weight from the application of the sealant to the occurrence of the curing reaction was confirmed using a thermogravimetric apparatus (TA-INSTRUMENTS, “TGA”).
- the organic EL display element sealants obtained in Examples 4 to 6 and Comparative Examples 2 and 5 were cured by heating at 100 ° C. for 30 minutes without irradiation with ultraviolet rays.
- the outgassing prevention property was evaluated as “ ⁇ ” when the vaporized component amount was less than 20 ppm, “ ⁇ ” when it was 20 ppm or more and less than 100 ppm, and “X” when it was 100 ppm or more.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Electroluminescent Light Sources (AREA)
- Epoxy Resins (AREA)
- Sealing Material Composition (AREA)
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| CN201480034096.1A CN105308092B (zh) | 2013-10-30 | 2014-10-20 | 有机el显示元件用密封剂 |
| JP2014556281A JP5703429B1 (ja) | 2013-10-30 | 2014-10-20 | 有機ｅｌ表示素子用封止剤 |
| KR1020157026903A KR102226349B1 (ko) | 2013-10-30 | 2014-10-20 | 유기 el 표시 소자용 밀봉제 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2015098519A (ja) * | 2013-11-18 | 2015-05-28 | 住友ベークライト株式会社 | 樹脂組成物、部材、光学装置および電子装置 |
| WO2017078006A1 (ja) * | 2015-11-06 | 2017-05-11 | 積水化学工業株式会社 | 有機エレクトロルミネッセンス表示素子用封止剤 |
| KR20170113221A (ko) | 2016-03-25 | 2017-10-12 | 도쿄 오카 고교 가부시키가이샤 | 에너지 감수성 조성물, 경화물 및 경화물의 제조 방법 |
| CN108350146A (zh) * | 2015-11-10 | 2018-07-31 | 日产化学工业株式会社 | 含长链伸烷基的环氧树脂组合物 |
| WO2020036234A1 (ja) * | 2018-08-17 | 2020-02-20 | 日産化学株式会社 | 防湿シール材用組成物 |
| JP2021527730A (ja) * | 2018-06-12 | 2021-10-14 | エルジー・ケム・リミテッド | 密封材組成物 |
| JP2023024361A (ja) * | 2021-08-06 | 2023-02-16 | イノックス・アドバンスト・マテリアルズ・カンパニー・リミテッド | 有機発光素子の封止材用熱硬化性液状組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR102416054B1 (ko) * | 2016-10-19 | 2022-07-01 | 세키스이가가쿠 고교가부시키가이샤 | 유기 el 표시 소자용 봉지제 및 유기 el 표시 소자용 봉지제의 제조 방법 |
| CN115232511B (zh) * | 2017-06-07 | 2023-11-24 | 积水化学工业株式会社 | 有机el显示元件用密封剂 |
| JP6966454B2 (ja) * | 2017-06-28 | 2021-11-17 | 積水化学工業株式会社 | 有機ｅｌ表示素子用面内封止剤及び有機ｅｌ表示素子用封止剤セット |
| WO2019045508A2 (ko) * | 2017-09-01 | 2019-03-07 | 주식회사 엘지화학 | 유기전자장치의 제조 방법 |
| JP7474052B2 (ja) * | 2018-03-30 | 2024-04-24 | 積水化学工業株式会社 | 有機ｅｌ表示素子用封止剤 |
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- 2014-10-20 KR KR1020157026903A patent/KR102226349B1/ko active IP Right Grant
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| JP2015098519A (ja) * | 2013-11-18 | 2015-05-28 | 住友ベークライト株式会社 | 樹脂組成物、部材、光学装置および電子装置 |
| WO2017078006A1 (ja) * | 2015-11-06 | 2017-05-11 | 積水化学工業株式会社 | 有機エレクトロルミネッセンス表示素子用封止剤 |
| CN107637168A (zh) * | 2015-11-06 | 2018-01-26 | 积水化学工业株式会社 | 有机电致发光显示元件用密封剂 |
| JPWO2017078006A1 (ja) * | 2015-11-06 | 2018-08-23 | 積水化学工業株式会社 | 有機エレクトロルミネッセンス表示素子用封止剤 |
| CN108350146A (zh) * | 2015-11-10 | 2018-07-31 | 日产化学工业株式会社 | 含长链伸烷基的环氧树脂组合物 |
| CN108350146B (zh) * | 2015-11-10 | 2021-03-16 | 日产化学工业株式会社 | 含长链伸烷基的环氧树脂组合物 |
| KR20170113221A (ko) | 2016-03-25 | 2017-10-12 | 도쿄 오카 고교 가부시키가이샤 | 에너지 감수성 조성물, 경화물 및 경화물의 제조 방법 |
| JP2021527730A (ja) * | 2018-06-12 | 2021-10-14 | エルジー・ケム・リミテッド | 密封材組成物 |
| WO2020036234A1 (ja) * | 2018-08-17 | 2020-02-20 | 日産化学株式会社 | 防湿シール材用組成物 |
| JP2023024361A (ja) * | 2021-08-06 | 2023-02-16 | イノックス・アドバンスト・マテリアルズ・カンパニー・リミテッド | 有機発光素子の封止材用熱硬化性液状組成物 |
| JP7445714B2 (ja) | 2021-08-06 | 2024-03-07 | イノックス・アドバンスト・マテリアルズ・カンパニー・リミテッド | 有機発光素子の封止材用熱硬化性液状組成物 |
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| Publication number | Publication date |
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| TWI614301B (zh) | 2018-02-11 |
| TW201527404A (zh) | 2015-07-16 |
| KR20160079728A (ko) | 2016-07-06 |
| KR102226349B1 (ko) | 2021-03-10 |
| CN105308092B (zh) | 2018-01-30 |
| CN105308092A (zh) | 2016-02-03 |
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