CN110999537A - 有机电致发光元件用密封剂 - Google Patents
有机电致发光元件用密封剂 Download PDFInfo
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- CN110999537A CN110999537A CN201880053942.2A CN201880053942A CN110999537A CN 110999537 A CN110999537 A CN 110999537A CN 201880053942 A CN201880053942 A CN 201880053942A CN 110999537 A CN110999537 A CN 110999537A
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- organic electroluminescent
- compound
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- electroluminescent element
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- 238000007789 sealing Methods 0.000 title claims abstract description 56
- -1 phosphoric acid compound Chemical class 0.000 claims abstract description 131
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 52
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 31
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 28
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 27
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 14
- 150000001334 alicyclic compounds Chemical class 0.000 claims abstract description 13
- 150000003014 phosphoric acid esters Chemical class 0.000 claims abstract description 7
- 239000000565 sealant Substances 0.000 claims description 44
- 150000002430 hydrocarbons Chemical group 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 25
- 229910019142 PO4 Inorganic materials 0.000 claims description 21
- 239000003822 epoxy resin Substances 0.000 claims description 19
- 239000010452 phosphate Substances 0.000 claims description 19
- 229920000647 polyepoxide Polymers 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 238000005401 electroluminescence Methods 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 11
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 10
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 239000003504 photosensitizing agent Substances 0.000 claims description 7
- 239000003566 sealing material Substances 0.000 claims description 7
- 230000001678 irradiating effect Effects 0.000 claims description 6
- 150000008301 phosphite esters Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 45
- 125000000217 alkyl group Chemical group 0.000 description 35
- 239000004593 Epoxy Substances 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 12
- 238000001723 curing Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000002723 alicyclic group Chemical group 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 7
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 230000035699 permeability Effects 0.000 description 6
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 6
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 5
- 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 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 125000005409 triarylsulfonium group Chemical group 0.000 description 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 5
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 4
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 4
- DXIYJLVGNSDKDI-UHFFFAOYSA-N [4-(4-benzoylphenyl)sulfanylphenyl]-diphenylsulfanium Chemical compound C=1C=C(SC=2C=CC(=CC=2)[S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 DXIYJLVGNSDKDI-UHFFFAOYSA-N 0.000 description 4
- 150000001454 anthracenes Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- ZLMKQJQJURXYLC-UHFFFAOYSA-N bis(2-ethylhexoxy)-oxophosphanium Chemical compound CCCCC(CC)CO[P+](=O)OCC(CC)CCCC ZLMKQJQJURXYLC-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 4
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 4
- 229940117972 triolein Drugs 0.000 description 4
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 4
- DECPGQLXYYCNEZ-UHFFFAOYSA-N tris(6-methylheptyl) phosphite Chemical compound CC(C)CCCCCOP(OCCCCCC(C)C)OCCCCCC(C)C DECPGQLXYYCNEZ-UHFFFAOYSA-N 0.000 description 4
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 3
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 3
- IOSONAGXTXMCDY-UHFFFAOYSA-N 4-(benzylsulfanylmethyl)phenol Chemical compound C1=CC(O)=CC=C1CSCC1=CC=CC=C1 IOSONAGXTXMCDY-UHFFFAOYSA-N 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- FUUNJHHNSDERSB-UHFFFAOYSA-N 5-(4-methoxyphenyl)thianthren-5-ium Chemical compound C1=CC(OC)=CC=C1[S+]1C2=CC=CC=C2SC2=CC=CC=C21 FUUNJHHNSDERSB-UHFFFAOYSA-N 0.000 description 3
- NYWSOZIZKAROHJ-UHFFFAOYSA-N 5-phenylthianthren-5-ium Chemical compound C12=CC=CC=C2SC2=CC=CC=C2[S+]1C1=CC=CC=C1 NYWSOZIZKAROHJ-UHFFFAOYSA-N 0.000 description 3
- KSMGAOMUPSQGTB-UHFFFAOYSA-N 9,10-dibutoxyanthracene Chemical compound C1=CC=C2C(OCCCC)=C(C=CC=C3)C3=C(OCCCC)C2=C1 KSMGAOMUPSQGTB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MOABYHZDQQELLG-UHFFFAOYSA-N OP(O)OP(O)O.C(CCCCCCCCCCCC)C(O)(C(CO)(CO)CO)CCCCCCCCCCCCC Chemical compound OP(O)OP(O)O.C(CCCCCCCCCCCC)C(O)(C(CO)(CO)CO)CCCCCCCCCCCCC MOABYHZDQQELLG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- ZUUNHCQWPCGZDH-UHFFFAOYSA-N [4-(4-benzoyl-2-chlorophenyl)sulfanylphenyl]-bis(4-fluorophenyl)sulfanium Chemical compound C1=CC(F)=CC=C1[S+](C=1C=CC(SC=2C(=CC(=CC=2)C(=O)C=2C=CC=CC=2)Cl)=CC=1)C1=CC=C(F)C=C1 ZUUNHCQWPCGZDH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000004292 cyclic ethers Chemical group 0.000 description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-O diphenylsulfanium Chemical compound C=1C=CC=CC=1[SH+]C1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-O 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- DWKWNUVRZPQFQZ-UHFFFAOYSA-N ethoxycarbonyl-ethyl-(naphthalen-2-ylmethyl)sulfanium Chemical compound C1=CC=CC2=CC(C[S+](CC)C(=O)OCC)=CC=C21 DWKWNUVRZPQFQZ-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 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 3
- 239000003999 initiator Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000004010 onium ions Chemical class 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 3
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 3
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 2
- HIYIGPVBMDKPCR-UHFFFAOYSA-N 1,1-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1(COC=C)CCCCC1 HIYIGPVBMDKPCR-UHFFFAOYSA-N 0.000 description 2
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 2
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 2
- XKZGIJICHCVXFV-UHFFFAOYSA-N 2-ethylhexyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCC(CC)CCCC)OC1=CC=CC=C1 XKZGIJICHCVXFV-UHFFFAOYSA-N 0.000 description 2
- YLUZWKKWWSCRSR-UHFFFAOYSA-N 3,9-bis(8-methylnonoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCC(C)C)OCC21COP(OCCCCCCCC(C)C)OC2 YLUZWKKWWSCRSR-UHFFFAOYSA-N 0.000 description 2
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ADALZNHBCNMMMB-UHFFFAOYSA-N C1=CC=C(C=C1)C(=O)CSSCC2=CC=C(C=C2)O Chemical compound C1=CC=C(C=C1)C(=O)CSSCC2=CC=C(C=C2)O ADALZNHBCNMMMB-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000511976 Hoya Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229930192627 Naphthoquinone Natural products 0.000 description 2
- QAEPIAHUOVJOOM-UHFFFAOYSA-N OP(O)OP(O)O.C(CCCCCCCC)C1=C(C=CC=C1)C(O)(C(CO)(CO)CO)C1=C(C=CC=C1)CCCCCCCCC Chemical compound OP(O)OP(O)O.C(CCCCCCCC)C1=C(C=CC=C1)C(O)(C(CO)(CO)CO)C1=C(C=CC=C1)CCCCCCCCC QAEPIAHUOVJOOM-UHFFFAOYSA-N 0.000 description 2
- BENNPBRBSFRLGP-UHFFFAOYSA-N OP(O)OP(O)O.C(CCCCCCCCC)C(O)(C(CO)(CO)CO)CCCCCCCCCC Chemical compound OP(O)OP(O)O.C(CCCCCCCCC)C(O)(C(CO)(CO)CO)CCCCCCCCCC BENNPBRBSFRLGP-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- RBRKCXPVSANVAF-UHFFFAOYSA-N [4-[4-(4-tert-butylbenzoyl)phenyl]sulfanylphenyl]-bis(4-methylphenyl)sulfanium Chemical compound C1=CC(C)=CC=C1[S+](C=1C=CC(SC=2C=CC(=CC=2)C(=O)C=2C=CC(=CC=2)C(C)(C)C)=CC=1)C1=CC=C(C)C=C1 RBRKCXPVSANVAF-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
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- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 2
- 150000001463 antimony compounds Chemical class 0.000 description 2
- 150000001495 arsenic compounds Chemical class 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- FLAJFZXTYPQIBY-CLFAGFIQSA-N bis[(z)-octadec-9-enyl] hydrogen phosphite Chemical compound CCCCCCCC\C=C/CCCCCCCCOP(O)OCCCCCCCC\C=C/CCCCCCCC FLAJFZXTYPQIBY-CLFAGFIQSA-N 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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Classifications
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- 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
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- 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
- C08G59/40—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 curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
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- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
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- 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
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- 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
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- 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
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- 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
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- 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
- H10K59/873—Encapsulations
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Power Engineering (AREA)
- Computer Hardware Design (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Microelectronics & Electronic Packaging (AREA)
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Abstract
一种有机电致发光元件用密封剂,其含有:(A)阳离子聚合性化合物、(B)光阳离子聚合引发剂、及(C)选自由磷酸酯及亚磷酸酯所组成的组中的一种以上磷酸化合物;且(A)阳离子聚合性化合物含有(A‑1)具有环氧基的脂环式化合物及(A‑2)具有环氧基的芳香族化合物。
Description
技术领域
本发明涉及一种有机电致发光元件用密封剂。例如,涉及一种用于有机电致发光元件密封用途的密封剂。
背景技术
近年来,使用有机电致发光(有机EL)显示元件或有机薄膜太阳能电池元件等有机薄膜元件的有机光器件的研究不断推进。有机薄膜元件可通过真空蒸镀或溶液涂布等而简便地制作,故而生产率优异。
有机电致发光显示元件具有于相互对向的一对电极间夹持有有机发光材料层的薄膜构造体。通过使电子自一电极注入至该有机发光材料层,并且使空穴自另一电极注入至该有机发光材料层,而于有机发光材料层内电子与空穴结合而进行自发光。有机电致发光显示元件与以背光装置为必需的液晶显示元件等相比,具有视觉识别性良好、可实现进一步薄型化、且可实现直流低电压驱动的优点。
然而,此种有机电致发光显示元件存在如下问题:若有机发光材料层或电极暴露于外部大气中,则其发光特性急剧劣化而寿命缩短。因此,为了提高有机电致发光显示元件的稳定性及耐久性,将有机电致发光显示元件中有机发光材料层或电极与大气中的水分或氧隔断的密封技术变得不可欠缺。
于专利文献1中,公开有于上表面发光型有机电致发光显示元件等中,于有机电致发光显示元件基板之间填满光固化性的密封剂,并照射光而进行密封的方法。然而,于专利文献1中,关于本发明的有机电致发光元件用密封剂,并无记载。
于专利文献2中,公开有于不使用反应性控制剂作为延迟固化剂的情况下,可确保充分的适用时间的UV固化性树脂组合物。然而,存在光照射后的适用时间较短的问题。专利文献2中,关于具有环氧基的脂环式化合物并无记载。专利文献2中,仅例示磷酸酯作为光阳离子聚合引发剂,于实施例中并不使用,为了抑制光照射后的粘度的上升,不使用磷酸酯。
于专利文献3中,公开有一种有机电致发光元件密封用粘接剂,其特征在于包含:含有环氧树脂(不包括“末端具有环氧基的聚环氧烷加成双酚衍生物”)、光阳离子聚合引发剂、以及末端具有环氧基的聚环氧烷加成双酚衍生物,且通过光照射而开始固化反应,即便将光遮断后也利用暗反应进行固化反应的光阳离子聚合性粘接剂。专利文献3中,关于具有环氧基的脂环式化合物并无记载。专利文献3存在如下问题:于光照射时产生释气而使元件劣化。
于专利文献4中,公开有含有特定的阳离子聚合性化合物、及光阳离子聚合引发剂的有机电致发光显示元件用密封剂。然而,存在光照射后的适用时间较短的问题。专利文献4中,仅例示磷酸酯作为光阳离子聚合引发剂,于实施例中并不使用,为了抑制光照射后的粘度的上升,不使用磷酸酯。
于专利文献5中,公开有一种利用后固化组合物的有机电致发光元件的密封方法,所述后固化组合物含有:光阳离子聚合性化合物100质量份、光阳离子聚合引发剂0.1~30质量份、包含具有醚键的化合物的固化控制剂0.1~30质量份,固化控制剂含有具有醚键的化合物。然而,于此种密封方法中,存在于光照射时产生释气而使元件劣化的问题。
专利文献5中,关于具有环氧基的脂环式化合物并无记载。专利文献5中,仅例示磷酸酯作为光阳离子聚合引发剂,于实施例中并不使用,为了抑制光照射后的粘度的上升,不使用磷酸酯。
于专利文献6中,公开有一种紫外线固化型树脂组合物,其含有:双酚A型环氧树脂与具有至少一个活性氢的磷酸类的加成物(A)、具有两个以上的脂环式环氧基的化合物(B)、及阳离子性光聚合引发剂(C)。然而,于使用此种(A)的树脂组合物中,(A)的制造方法较为复杂,存在因副产物而产生释气而使元件劣化的问题。专利文献6中,关于有机电致发光元件用密封剂并无记载。
于专利文献7中,公开有包含辐射线固化性成分、并且包含属于不同的化合物组中的至少两种阻燃剂的辐射线固化性组合物。然而,专利文献7首先是用于其他目的的阻燃性的固化性组合物,并无关于光照射后的适用时间及光照射时的释气产生的记载。专利文献7中,关于有机电致发光元件用密封剂,并无记载。
现有技术文献
专利文献
专利文献1:日本专利特开2001-357973号公报
专利文献2:日本专利5919574号公报
专利文献3:日本专利4800247号公报
专利文献4:日本专利特开2016-58273号公报
专利文献5:日本专利4384509号公报
专利文献6:日本专利特开平7-247342号公报
专利文献7:日本专利特表2007-513234号公报
发明内容
发明要解决的问题
本发明是鉴于上述情况而完成者,其目的在于提供一种光照射后的粘度的上升较少、且不易使有机电致发光元件劣化的有机电致发光元件用密封剂。
用于解决问题的方案
即,本发明如下所述。
<1>一种有机电致发光元件用密封剂,其含有(A)阳离子聚合性化合物、(B)光阳离子聚合引发剂、及(C)选自由磷酸酯及亚磷酸酯所组成的组中的一种以上磷酸化合物,且(A)阳离子聚合性化合物含有(A-1)具有环氧基的脂环式化合物及(A-2)具有环氧基的芳香族化合物。
<2>如<1>所述的有机电致发光元件用密封剂,其中,(C)磷酸化合物为(C1)磷酸酯。
<3>如<2>所述的有机电致发光元件用密封剂,其中,(C1)磷酸酯含有选自由式(C1-1)所表示的化合物、式(C1-2)所表示的化合物及式(C1-3)所表示的化合物所组成的组中的至少一种:
[式中,R1、R2、R3、R4、R5及R6分别独立地表示任选具有取代基的烃基]。
<4>如<1>所述的有机电致发光元件用密封剂,其中(C)磷酸化合物为(C2)亚磷酸酯。
<5>如<4>所述的有机电致发光元件用密封剂,其中,(C2)亚磷酸酯含有选自由式(C2-1)所表示的化合物、式(C2-2)所表示的化合物、式(C2-3)所表示的化合物、式(C2-4)所表示的化合物、式(C2-5)所表示的化合物及式(C2-6)所表示的化合物所组成的组中的至少一种:
[式中,R7、R8、R9、R10、R11、R12、R13、R14、R15、R16及R17分别独立地表示任选具有取代基的烃基]。
<6>如<1>至<5>中任一项所述的有机电致发光元件用密封剂,其中(A-2)具有环氧基的芳香族化合物为选自由双酚A型环氧树脂、双酚F型环氧树脂所组成的组中的一种以上。
<7>如<1>至<6>中任一项所述的有机电致发光元件用密封剂,其中,(B)光阳离子聚合引发剂为鎓盐。
<8>如<1>至<7>中任一项所述的有机电致发光元件用密封剂,其中,(B)光阳离子聚合引发剂的使用量相对于(A)阳离子聚合性化合物100质量份,为0.05~5.0质量份。
<9>如<1>至<8>中任一项所述的有机电致发光元件用密封剂,其还含有光敏剂。
<10>如<1>至<9>中任一项所述的有机电致发光元件用密封剂,其还含有硅烷偶联剂。
<11>一种固化体,其是如<1>至<10>中任一项所述的有机电致发光元件用密封剂的固化体。
<12>一种有机电致发光元件用密封材料,其包含如<11>所述的固化体。
<13>一种有机电致发光显示设备,其包含有机电致发光元件、及如<12>所述的有机电致发光元件用密封材料。
<14>一种有机电致发光显示设备的制造方法,其具有:附着步骤,其使如<1>至<10>中任一项所述的有机电致发光元件用密封剂附着于第一构件;照射步骤,其对所附着的上述有机电致发光元件用密封剂照射光;及贴合步骤,其借助经光照射的上述有机电致发光元件用密封剂而将上述第一构件与第二构件贴合。
<15>如<14>所述的有机电致发光显示设备的制造方法,其中,上述第一构件为基板,上述第二构件为有机电致发光元件。
发明的效果
根据本发明,可提供一种光照射后的粘度的上升较少、且不易使有机电致发光元件劣化的有机电致发光元件用密封剂。
具体实施方式
以下,详细地说明本实施方式。
本实施方式的有机电致发光元件用密封剂的特征在于,含有:
(A)阳离子聚合性化合物、
(B)光阳离子聚合引发剂、及
(C)选自由磷酸酯及亚磷酸酯所组成的组中的至少一种磷酸化合物。
此外,本实施方式的有机电致发光元件用密封剂的特征在于:(A)阳离子聚合性化合物含有(A-1)具有环氧基的脂环式化合物、及(A-2)具有环氧基的芳香族化合物。
其次,对本实施方式的有机电致发光元件用密封剂的成分进行说明。
(A)阳离子聚合性化合物
本实施方式的有机电致发光元件用密封剂以(A)阳离子聚合性化合物作为必需成分。(A)阳离子聚合性化合物优选为光聚合性。
(A)阳离子聚合性化合物含有(A-1)具有环氧基的脂环式化合物及(A-2)具有环氧基的芳香族化合物。由此,可获得良好的粘接性及低透湿性。
(A-1)具有环氧基的脂环式化合物
作为具有环氧基的脂环式化合物(以下,亦称为脂环式环氧化合物),可列举:通过将具有至少一个环烯烃环(例如,环己烯环、环戊烯环、蒎烯环等)的化合物利用过氧化氢、过酸等适当的氧化剂进行环氧化所获得的化合物或其衍生物,或使芳香族环氧化合物(例如,双酚A型环氧树脂、双酚F型环氧树脂等)氢化所获得的氢化环氧化合物等。这些化合物也可选择一种以上而使用。
作为脂环式环氧化合物,可列举:3',4'-环氧环己基甲基-3,4-环氧环己烷羧酸酯、(甲基)丙烯酸3,4-环氧环己基烷基酯(例如,(甲基)丙烯酸3,4-环氧环己基甲酯等)、(3,3',4,4'-二环氧基)联环己烷、氢化双酚A型环氧树脂、氢化双酚F型环氧树脂等。
脂环式环氧化合物中,优选为具有1,2-环氧环己烷结构的脂环式环氧化合物。具有1,2-环氧环己烷结构的脂环式环氧化合物中,优选为下述式(A1-1)所表示的化合物。
(式(A1-1)中,X表示单键或连接基团(具有1个以上的原子的二价基团),连接基团为二价的烃基、羰基、醚键、酯键、碳酸酯基、酰胺键、或多个这些连接而成的基团)
X优选为连接基团。连接基团中,优选为具有酯键的官能团。这些中,优选为3',4'-环氧环己基甲基-3,4-环氧环己烷羧酸酯。
关于脂环式环氧化合物的分子量,就透湿性或保存稳定性的方面而言,优选为450以下,更优选为400以下,进而优选为不足300,进而优选为100~280。
脂环式环氧化合物具有分子量分布的情况下,优选脂环式环氧化合物的数均分子量为上述范围。需要说明的是,于本说明书中,数均分子量表示通过凝胶渗透色谱法(GPC,Gel Permeation Chromatograph)并利用下述测定条件所测得的聚苯乙烯换算的值。
·溶剂(流动相):THF(Tetrahydrofuran,四氢呋喃)
·脱气装置:ERMA公司制造的ERC-3310
·泵:日本分光公司制造的PU-980
·流速:1.0ml/min
·自动取样器:Tosoh公司制造的AS-8020
·柱烘箱:日立制作所制造的L-5030
·设定温度:40℃
·柱构成:两根Tosoh公司制造的TSKguardcolumnMP(×L)6.0mmID×4.0cm、及两根Tosoh公司制造的TSK-GELMULTIPORE HXL-M 7.8mmID×30.0cm,合计4根
·检测器:RI日立制作所制造的L-3350
·数据处理:SIC480数据站
(A-2)具有环氧基的芳香族化合物
作为具有环氧基的芳香族化合物(以下,有时亦称为芳香族环氧化合物),可使用单体、低聚物或聚合物的任意种,可列举:双酚A型环氧树脂、双酚F型环氧树脂、双酚S型环氧树脂、联苯型环氧树脂、萘型环氧树脂、芴型环氧树脂、酚醛清漆苯酚型环氧树脂、甲酚酚醛清漆型环氧树脂、它们的改性物等。这些环氧树脂也可选择一种以上而使用。
这些中,优选为具有双酚结构的芳香族环氧化合物。具有双酚结构的芳香族环氧化合物中,优选为下述式(A2-1)所表示的化合物。
(式(A2-1)中,n表示0.1~30的实数,R21、R22、R23及R24分别独立地表示氢原子或经取代或未经取代的碳原子数1~5的烷基)。
R21、R22、R23、R24优选为氢原子或甲基。R21、R22、R23、R24优选为相同。
于具有双酚结构的芳香族环氧化合物中,优选为选自由双酚A型环氧树脂及双酚F型环氧树脂所组成的组中的一种以上。
关于芳香族环氧化合物的分子量,就透湿性等方面而言,优选为100~5000,更优选为150~1000,最优选为200~450。
芳香族环氧化合物具有分子量分布的情况下,优选芳香族环氧化合物的数均分子量为上述范围。需要说明的是,本说明书中,数均分子量表示通过凝胶渗透色谱法(GPC)并利用上述测定条件所测得的聚苯乙烯换算的值。
本实施方式的(A)阳离子聚合性化合物可使用单体、低聚物或聚合物的任意种。
本实施方式的(A)阳离子聚合性化合物优选为环氧化合物。
本实施方式的(A)阳离子聚合性化合物优选为具有两个以上的环状醚基、阳离子聚合性乙烯基等阳离子聚合性基团,更优选为具有两个。
于本实施方式中,可进而使用除(A-1)及(A-2)以外的其他阳离子聚合性化合物。作为除(A-1)及(A-2)以外的其他阳离子聚合性化合物,可列举:环状醚类、阳离子聚合性乙烯基化合物等。作为环状醚类,可列举:环氧、氧杂环丁烷等化合物。
(A)阳离子聚合性化合物100质量份中,除(A-1)及(A-2)以外的其他阳离子聚合性化合物的含量优选为40质量份以下,更优选为20质量份以下,最优选为10质量份以下。(A)阳离子聚合性化合物100质量份中,除(A-1)及(A-2)以外的其他阳离子聚合性化合物的含量例如可为1质量份以上,可为5质量份以上,亦可为0质量份。
作为阳离子聚合性乙烯基化合物,可列举:乙烯醚、乙烯胺、苯乙烯等。这些化合物或衍生物也可选择一种以上而使用。
除(A-1)及(A-2)以外的其他阳离子聚合性化合物中,优选包含二缩水甘油醚化合物、氧杂环丁烷化合物、乙烯醚化合物的一种以上。
作为二缩水甘油醚化合物,可列举:亚烷基二醇的二缩水甘油醚(例如,乙二醇的二缩水甘油醚、丙二醇的二缩水甘油醚、1,6-己二醇的二缩水甘油醚等)、多元醇的聚缩水甘油醚(例如,甘油或其环氧烷加成物的二或三缩水甘油醚等)、聚亚烷基二醇的二缩水甘油醚(例如,聚乙二醇或其环氧烷加成物的二缩水甘油醚、聚丙二醇或其环氧烷加成物的二缩水甘油醚等)。此处,作为环氧烷,可列举:环氧乙烷及环氧丙烷等脂肪族系。
作为氧杂环丁烷化合物,并无特别限定,可列举:3-乙基-3-羟基甲基氧杂环丁烷(东亚合成株式会社制造的商品名ARONE OXETANE OXT-101等)、1,4-双[(3-乙基-3-氧杂环丁基)甲氧基甲基]苯(东亚合成株式会社制造的商品名ARONE OXETANEOXT-121等)、3-乙基-3-(苯氧基甲基)氧杂环丁烷(东亚合成株式会社制造的商品名ARONE OXETANEOXT-211等)、二(1-乙基-(3-氧杂环丁基))甲醚(东亚合成株式会社制造的商品名ARONEOXETANEOXT-221等)、3-乙基-3-(2-乙基己氧基甲基)氧杂环丁烷(东亚合成株式会社制造的商品名ARONE OXETANEOXT-212等)等。所谓氧杂环丁烷化合物,是指于分子内具有一个以上的氧杂环丁烷环的化合物。
作为乙烯醚化合物,并无特别限定,可列举:乙二醇二乙烯醚、乙二醇单乙烯醚、二乙二醇二乙烯醚、三乙二醇单乙烯醚、三乙二醇二乙烯醚、丙二醇二乙烯醚、二丙二醇二乙烯醚、丁二醇二乙烯醚、己二醇二乙烯醚、环己烷二甲醇二乙烯醚、羟基乙基单乙烯醚、羟基壬基单乙烯醚、三羟甲基丙烷三乙烯醚等二或三乙烯醚化合物、乙基乙烯醚、正丁基乙烯醚、异丁基乙烯醚、十八烷基乙烯醚、环己基乙烯醚、羟基丁基乙烯醚、2-乙基己基乙烯醚、环己烷二甲醇单乙烯醚、正丙基乙烯醚、异丙基乙烯醚、异丙烯醚邻碳酸亚丙酯、十二烷基乙烯醚、二乙二醇单乙烯醚、十八烷基乙烯醚等单乙烯醚化合物等。
关于(A-1)具有环氧基的脂环式化合物的使用量,于(A)阳离子聚合性化合物100质量份中,优选为30~95质量份,更优选为50~90质量份,最优选为60~80质量份,进而更优选为65~75质量份。若为30质量份以上,则可获得耐久性,若为95质量份以下,则可获得耐久性。
关于(A-2)具有环氧基的芳香族化合物的使用量,于(A)阳离子聚合性化合物100质量份中,优选为5~70质量份,更优选为10~50质量份,最优选为20~40质量份,进而更优选为25~35质量份。若为5质量份以上,则可获得耐久性,若为70质量份以下,则可获得耐久性。
(A)阳离子聚合性化合物100质量份中,(A-1)具有环氧基的脂环式化合物与(A-2)具有环氧基的芳香族化合物的合计含量优选为60质量份以上,更优选为80质量份以上,最优选为90质量份以上,进而更优选为100质量份。
(B)光阳离子聚合引发剂
本实施方式的有机电致发光元件用密封剂以(B)光阳离子聚合引发剂作为必需成分。在使用光阳离子聚合引发剂的情况下,本实施方式的密封剂可通过紫外线等能量射线照射而固化。
作为(B)光阳离子聚合引发剂,并无特别限定,可列举:芳基锍盐衍生物(例如,DowChemical公司制造的Cyracure UVI-6990、Cyracure UVI-6974、旭电化工业公司制造的AdekaOptomer SP-150、AdekaOptomer SP-152、AdekaOptomer SP-170、AdekaOptomer SP-172、SAN-APRO公司制造的CPI-100P、CPI-101A、CPI-200K、CPI-210S、LW-S1、Double Bond公司制造的Cibacure 1190等)、芳基碘鎓盐衍生物(例如,Ciba Specialty Chemicals公司制造的Irgacure 250、Rhodia Japan公司制造的RP-2074)、丙二烯-离子络合物衍生物、重氮鎓盐衍生物、三嗪系引发剂及其他卤化物等产酸剂等。作为光阳离子聚合引发剂的阳离子种,优选为式(B-1)所表示的鎓盐。
作为(B)光阳离子聚合引发剂,并无特别限定,可列举:式(B-1)所表示的鎓盐。
(A表示VIA族~VIIA族的原子价m的元素;m表示1~2;p表示0~3;m、p优选为整数;R表示键合于A的有机基团;D表示下述式(B-1-1)所表示的二价基团:
式(B-1-1)中,E表示二价基团,G表示-O-、-S-、-SO-、-SO2-、-NH-、-NR'-、-CO-、-COO-、-CONH-、碳数1~3的亚烷基或亚苯基(R'为碳数1~5的烷基或碳数6~10的芳基);a表示0~5;a+1个E及A个G可分别相同亦可不同;a优选为整数;X-为鎓的抗衡离子;其个数为每1分子为p+1)。
式(B-1-1)的鎓离子并无特别限定,可列举:4-(苯硫基)苯基二苯基锍、双[4-(二苯基锍基)苯基]硫醚、双[4-{双[4-(2-羟基乙氧基)苯基]锍基}苯基]硫醚、双{4-[双(4-氟苯基)锍基]苯基}硫醚、4-(4-苯甲酰基-2-氯苯硫基)苯基双(4-氟苯基)锍、4-(4-苯甲酰基苯硫基)苯基二苯基锍、7-异丙基-9-氧基-10-硫杂-9,10-二氢蒽-2-基二对甲苯锍、7-异丙基-9-氧基-10-硫杂-9,10-二氢蒽-2-基二苯基锍、2-[(二对甲苯基)锍基]噻吨酮、2-[(二苯基)锍基]噻吨酮、4-[4-(4-叔丁基苯甲酰基)苯硫基]苯基二对甲苯锍、4-(4-苯甲酰基苯硫基)苯基二苯基锍、5-(4-甲氧基苯基)噻蒽(thiaanthrenium)、5-苯基噻蒽、二苯基苯甲酰甲基锍、4-羟基苯基甲基苄基锍、2-萘基甲基(1-乙氧基羰基)乙基锍、4-羟基苯基甲基苯甲酰甲基锍、十八烷基甲基苯甲酰甲基锍等。
R是键合于A的有机基团。R表示例如碳数6~30的芳基、碳数4~30的杂环基、碳数1~30的烷基、碳数2~30的烯基或碳数2~30的炔基,这些基团也可被选自由烷基、羟基、烷氧基、烷羰基、芳基羰基、烷氧基羰基、芳氧基羰基、芳基硫羰基、酰氧基、芳硫基、烷硫基、芳基、杂环、芳氧基、烷基亚磺酰基、芳基亚磺酰基、烷基磺酰基、芳基磺酰基、亚烷基氧基、氨基、氰基、硝基的各基团及卤素所组成的组中的至少1种所取代。R的个数为m+p(m-1)+1,可相互相同,亦可不同。此外,两个以上的R相互也可直接或经由-O-、-S-、-SO-、-SO2-、-NH-、-NR'-、-CO-、-COO-、-CONH-、碳数1~3的亚烷基或亚苯基键合而形成包含元素A的环结构。此处,R'为碳数1~5的烷基或碳数6~10的芳基。
上述碳数6~30的芳基、碳数4~30的杂环基、碳数1~30的烷基、碳数2~30的烯基或碳数2~30的炔基也可具有至少1种取代基,作为取代基的例子,可列举:甲基、乙基、丙基、丁基、戊基、辛基、癸基、十二烷基、十四烷基、十六烷基、十八烷基等碳数1~18的直链烷基;异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、叔戊基、异己基等碳数1~18的支链烷基;环丙基、环丁基、环戊基、环己基等碳数3~18的环烷基;羟基;甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、己氧基、癸氧基、十二烷氧基等碳数1~18的直链或支链的烷氧基;乙酰基、丙酰基、丁酰基、2-甲基丙酰基、庚酰基、2-甲基丁酰基、3-甲基丁酰基、辛酰基、癸酰基、十二碳酰基、十八碳酰基等碳数2~18的直链或支链的烷羰基;苯甲酰基、萘甲酰基等碳数7~11的芳基羰基;甲氧基羰基、乙氧基羰基、丙氧基羰基、异丙氧基羰基、丁氧基羰基、异丁氧基羰基、仲丁氧基羰基、叔丁氧基羰基、辛氧基羰基、十四烷氧基羰基、十八烷氧基羰基等碳数2~19的直链或支链的烷氧基羰基;苯氧基羰基、萘氧基羰基等碳数7~11的芳氧基羰基;苯硫基羰基、萘氧基硫羰基等碳数7~11的芳基硫羰基;乙酰氧基、乙基羰氧基、丙基羰氧基、异丙基羰氧基、丁基羰氧基、异丁基羰氧基、仲丁基羰氧基、叔丁基羰氧基、辛基羰氧基、十四烷基羰氧基、十八烷羰氧基等碳数2~19的直链或支链的酰氧基;苯硫基、2-甲基苯硫基、3-甲基苯硫基、4-甲基苯硫基、2-氯苯硫基、3-氯苯硫基、4-氯苯硫基、2-溴苯硫基、3-溴苯硫基、4-溴苯硫基、2-氟苯硫基、3-氟苯硫基、4-氟苯硫基、2-羟基苯硫基、4-羟基苯硫基、2-甲氧基苯硫基、4-甲氧基苯硫基、1-萘硫基、2-萘硫基、4-[4-(苯硫基)苯甲酰基]苯硫基、4-[4-(苯硫基)苯氧基]苯硫基、4-[4-(苯硫基)苯基]苯硫基、4-(苯硫基)苯硫基、4-苯甲酰基苯硫基、4-苯甲酰基-2-氯苯硫基、4-苯甲酰基-3-氯苯硫基、4-苯甲酰基-3-甲硫基苯硫基、4-苯甲酰基-2-甲硫基苯硫基、4-(4-甲硫基苯甲酰基)苯硫基、4-(2-甲硫基苯甲酰基)苯硫基、4-(对甲基苯甲酰基)苯硫基、4-(对乙基苯甲酰基)苯硫基、4-(对异丙基苯甲酰基)苯硫基、4-(对叔丁基苯甲酰基)苯硫基等碳数6~20的芳硫基;甲硫基、乙硫基、丙硫基、异丙硫基、丁硫基、异丁硫基、仲丁硫基、叔丁硫基、戊硫基、异戊硫基、新戊硫基、叔戊硫基、辛硫基、癸硫基、十二烷硫基等碳数1~18的直链或支链的烷硫基;苯基、甲苯基、二甲基苯基、萘基等碳数6~10的芳基;噻吩基、呋喃基、吡喃基、吡咯基、噁唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、吲哚基、苯并呋喃基、苯并噻吩基、喹啉基、异喹啉基、喹喔啉基、喹唑啉基、咔唑基、吖啶基、吩噻嗪基、吩嗪基、呫吨基、噻蒽基、吩噁嗪基(Phenoxazinyl)、吩噁噻基(phenoxathiinyl)、苯并二氢吡喃基(chromanyl)、异苯并二氢吡喃基、二苯并噻吩基、呫吨酮基、噻吨酮基、二苯并呋喃基等碳数4~20的杂环基;苯氧基、萘氧基等碳数6~10的芳氧基;甲基亚磺酰基、乙基亚磺酰基、丙基亚磺酰基、异丙基亚磺酰基、丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基、叔丁基亚磺酰基、戊基亚磺酰基、异戊基亚磺酰基、新戊基亚磺酰基、叔戊基亚磺酰基、辛基亚磺酰基等碳数1~18的直链或支链的烷基亚磺酰基;苯基亚磺酰基、甲苯基亚磺酰基、萘基亚磺酰基等碳数6~10的芳基亚磺酰基;甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基、丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、戊基磺酰基、异戊基磺酰基、新戊基磺酰基、叔戊基磺酰基、辛基磺酰基等碳数1~18的直链或支链的烷基磺酰基;苯基磺酰基、甲苯基磺酰基(甲苯磺酰基)、萘基磺酰基等碳数6~10的芳基磺酰基;式(B-1-2)所表示的亚烷基氧基,
(式中,Q表示氢原子或甲基,k表示1~5的整数);未经取代的氨基;经碳数1~5的烷基及/或碳数6~10的芳基进行了单取代或二取代的氨基;氰基;硝基;氟、氯、溴、碘等卤素等。
式(B-1)中的p表示[D-A+Rm-1]键的重复单元数,优选为0~3的整数。
作为式(B-1)中的鎓离子[A+],优选为锍、碘鎓、硒鎓,作为代表例,可列举以下离子。
作为锍离子,可列举:三苯基锍、三对甲苯锍、三邻甲苯锍、三(4-甲氧基苯基)锍、1-萘基二苯基锍、2-萘基二苯基锍、三(4-氟苯基)锍、三-1-萘基锍、三-2-萘基锍、三(4-羟基苯基)锍、4-(苯硫基)苯基二苯基锍、4-(对甲苯硫基)苯基二对甲苯锍、4-(4-甲氧基苯硫基)苯基双(4-甲氧基苯基)锍、4-(苯硫基)苯基双(4-氟苯基)锍、4-(苯硫基)苯基双(4-甲氧基苯基)锍、4-(苯硫基)苯基二对甲苯锍、双[4-(二苯基锍基)苯基]硫醚、双[4-{双[4-(2-羟基乙氧基)苯基]锍基}苯基]硫醚、双{4-[双(4-氟苯基)锍基]苯基}硫醚、双{4-[双(4-甲基苯基)锍基]苯基}硫醚、双{4-[双(4-甲氧基苯基)锍基]苯基}硫醚、4-(4-苯甲酰基-2-氯苯硫基)苯基双(4-氟苯基)锍、4-(4-苯甲酰基-2-氯苯硫基)苯基二苯基锍、4-(4-苯甲酰基苯硫基)苯基双(4-氟苯基)锍、4-(4-苯甲酰基苯硫基)苯基二苯基锍、7-异丙基-9-氧基-10-硫杂-9,10-二氢蒽-2-基二对甲苯锍、7-异丙基-9-氧基-10-硫杂-9,10-二氢蒽-2-基二苯基锍、2-[(二对甲苯基)锍基]噻吨酮、2-[(二苯基)锍基]噻吨酮、4-[4-(4-叔丁基苯甲酰基)苯硫基]苯基二对甲苯锍、4-[4-(4-叔丁基苯甲酰基)苯硫基]苯基二苯基锍、4-[4-(苯甲酰基苯硫基)]苯基二对甲苯锍、4-[4-(苯甲酰基苯硫基)]苯基二苯基锍、5-(4-甲氧基苯基)噻蒽、5-苯基噻蒽、5-甲苯基噻蒽、5-(4-乙氧基苯基)噻蒽、5-(2,4,6-三甲基苯基)噻蒽等三芳基锍;二苯基苯甲酰甲基锍、二苯基4-硝基苯甲酰甲基锍、二苯基苄基锍、二苯基甲基锍等二芳基锍;苯基甲基苄基锍、4-羟基苯基甲基苄基锍、4-甲氧基苯基甲基苄基锍、4-乙酰羰氧基苯基甲基苄基锍、2-萘基甲基苄基锍、2-萘基甲基(1-乙氧基羰基)乙基锍、苯基甲基苯甲酰甲基锍、4-羟基苯基甲基苯甲酰甲基锍、4-甲氧基苯基甲基苯甲酰甲基锍、4-乙酰羰氧基苯基甲基苯甲酰甲基锍、2-萘基甲基苯甲酰甲基锍、2-萘基十八烷基苯甲酰甲基锍、9-蒽基甲基苯甲酰甲基锍等单芳基锍;二甲基苯甲酰甲基锍、苯甲酰甲基四氢噻吩鎓、二甲基苄基锍、苄基四氢噻吩鎓、十八烷基甲基苯甲酰甲基锍等三烷基锍等。
这些鎓离子中,优选为包含锍离子与碘鎓离子的1种以上,更优选为锍离子。作为锍离子,优选包含如下物质的1种以上:三苯基锍、三对甲苯锍、4-(苯硫基)苯基二苯基锍、双[4-(二苯基锍基)苯基]硫醚、双[4-{双[4-(2-羟基乙氧基)苯基]锍基}苯基]硫醚、双{4-[双(4-氟苯基)锍基]苯基}硫醚、4-(4-苯甲酰基-2-氯苯硫基)苯基双(4-氟苯基)锍、4-(4-苯甲酰基苯硫基)苯基二苯基锍、7-异丙基-9-氧基-10-硫杂-9,10-二氢蒽-2-基二对甲苯锍、7-异丙基-9-氧基-10-硫杂-9,10-二氢蒽-2-基二苯基锍、2-[(二对甲苯基)锍基]噻吨酮、2-[(二苯基)锍基]噻吨酮、4-[4-(4-叔丁基苯甲酰基)苯硫基]苯基二对甲苯锍、4-[4-(苯甲酰基苯硫基)]苯基二苯基锍、5-(4-甲氧基苯基)噻蒽、5-苯基噻蒽、二苯基苯甲酰甲基锍、4-羟基苯基甲基苄基锍、2-萘基甲基(1-乙氧基羰基)乙基锍、4-羟基苯基甲基苯甲酰甲基锍及十八烷基甲基苯甲酰甲基锍。
式(B-1)中,X-为抗衡离子。其个数为每1分子为p+1。抗衡离子并无特别限定,可列举:硼化合物、磷化合物、锑化合物、砷化合物、烷基磺酸化合物等的卤化物、甲基化物化合物等。作为X-,例如可列举:F-、Cl-、Br-、I-等卤素离子;OH-;ClO4 -;FSO3 -、ClSO3 -、CH3SO3 -、C6H5SO3 -、CF3SO3 -等磺酸根离子类;HSO4 -、SO4 2-等硫酸根离子类;HCO3 -、CO3 2-等碳酸根离子类;H2PO4 -、HPO4 2-、PO4 3-等磷酸根离子类;PF6 -、PF5OH-、氟化烷基氟磷酸离子等氟磷酸离子类;BF4 -、B(C6F5)4 -、B(C6H4CF3)4 -等硼酸离子类;AlCl4 -;BiF6 -等。此外,可列举:SbF6 -、SbF5OH-等氟锑酸离子类、或AsF6 -、AsF5OH-等氟砷酸离子类等。
作为氟化烷基氟磷酸离子,可列举:式(B-1-3)等所表示的氟化烷基氟磷酸离子等。
[(Rf)bPF6-b]- (B-1-3)
式(B-1-3)中,Rf表示经氟原子所取代的烷基。Rf的个数b优选为1~5,且为整数。b个Rf可分别相同亦可不同。Rf的个数b更优选为2~4,最优选为2~3。
式(B-1-3)所表示的氟化烷基氟磷酸离子中,Rf表示经氟原子所取代的烷基,优选的碳数为1~8,进而优选的碳数为1~4。作为烷基,可列举:甲基、乙基、丙基、丁基、戊基、辛基等直链烷基;异丙基、异丁基、仲丁基、叔丁基等支链烷基;进而环丙基、环丁基、环戊基、环己基等环烷基等。作为具体例,可列举:CF3、CF3CF2、(CF3)2CF、CF3CF2CF2、CF3CF2CF2CF2、(CF3)2CFCF2、CF3CF2(CF3)CF、(CF3)3C等。
作为优选的氟化烷基氟磷酸阴离子的具体例,可列举:[(CF3CF2)2PF4]-、[(CF3CF2)3PF3]-、[((CF3)2CF)2PF4]-、[((CF3)2CF)3PF3]-、[(CF3CF2CF2)2PF4]-、[(CF3CF2CF2)3PF3]-、[((CF3)2CFCF2)2PF4]-、[((CF3)2CFCF2)3PF3]-、[(CF3CF2CF2CF2)2PF4]-及[(CF3CF2CF2CF2)3PF3]-等。
关于光阳离子聚合引发剂,为了使在环氧化合物、环氧树脂中的溶解变得容易,也可使用预先溶解于溶剂类中的引发剂。作为溶剂类,例如可列举:碳酸亚丙酯、碳酸亚乙酯、碳酸1,2-亚丁酯、碳酸二甲酯、碳酸二乙酯等碳酸酯类等。
这些光阳离子聚合引发剂也可选择1种以上而使用。
作为(B)光阳离子聚合引发剂的阴离子种,可列举:硼化合物、磷化合物、锑化合物、砷化合物、烷基磺酸化合物等的卤化物等。这些阴离子种也可选择1种以上而使用。这些中,就光固化性优异、提高粘接性、粘接耐久性的方面而言,优选为氟化物。氟化物中,优选为六氟锑酸盐。
(B)光阳离子聚合引发剂中,优选包含式(B-2)所表示的三芳基锍盐六氟锑酸盐、式(B-3)所表示的二苯基4-硫代苯氧基苯基锍三(五氟乙基)三氟磷酸盐的1种以上,更优选为三芳基锍盐六氟锑酸盐。
(B)光阳离子聚合引发剂的使用量相对于(A)阳离子聚合性化合物100质量份,优选为0.05~5质量份,更优选为0.1~3质量份。若光阳离子聚合引发剂的使用量为0.05质量份以上,则没有光固化性变差的情况,若为5质量份以下,则也没有使粘接耐久性降低的情况。
(C)磷酸化合物
本实施方式的有机电致发光元件用密封剂以(C)磷酸化合物作为必需成分。磷酸化合物为选自由(C1)磷酸酯与(C2)亚磷酸酯所组成的组中的1种以上。作为磷酸化合物,优选为有机磷酸化合物。磷酸化合物中,优选为(C1)磷酸酯。
作为(C1)磷酸酯,可列举:磷酸二乙基苄酯、磷酸三甲酯、磷酸三乙酯、磷酸三正丁酯、磷酸三(丁氧基乙基)酯、磷酸三(2-乙基己基)酯、(RO)3P=O[R=月桂基、鲸蜡基、硬脂基或油基]、磷酸三(2-氯乙基)酯、磷酸三(2-二氯丙基)酯、磷酸三苯酯、焦磷酸丁酯、磷酸三甲苯酯、磷酸三(二甲苯)酯、磷酸辛基二苯酯、磷酸甲苯基二苯酯、二甲苯二磷酸酯、磷酸单丁酯、磷酸二丁酯、磷酸二-2-乙基己酯、磷酸单异癸酯、酸性磷酸乙基铵(Ammoniumethyl acid phosphate)、及酸性磷酸2-乙基己酯盐等。
(C1)磷酸酯优选含有选自由式(C1-1)所表示的化合物、式(C1-2)所表示的化合物及式(C1-3)所表示的化合物所组成的组中的至少一种,更优选含有式(C1-2)所表示的化合物。
式(C1-1)、式(C1-2)及式(C1-3)中,R1、R2、R3、R4、R5及R6分别独立地表示任选具有取代基的烃基。
式(C1-2)中的R2、R3及R4、及式(C1-3)中的R5及R6优选为在各式中为相同的基团。
作为R1、R2、R3、R4、R5及R6中的烃基任选具有的取代基,例如可列举:氧烷基等。R1、R2、R3、R4、R5及R6中的烃基优选为未经取代的烃基。
R1、R2、R3、R4、R5及R6中的烃基优选为烷基或芳基,更优选为烷基或苯基,进而优选为烷基。烷基的碳原子数例如可以为1~18,优选为4~13。
作为式(C1-1)所表示的化合物,例如也可为磷酸单烷基酯(即,R1为烷基的化合物)等,作为具体例,可列举:磷酸单乙酯、磷酸单正丁酯、磷酸单(丁氧基乙基)酯、磷酸单(2-乙基己基)酯等。
作为式(C1-2)所表示的化合物,优选为磷酸三烷基酯(即,R2、R3及R4为烷基的化合物)。此时,R2、R3及R4的烷基的碳原子数优选为1~18,更优选为4~12,进而优选为8。
作为磷酸三烷基酯的具体例,可列举:磷酸三乙酯、磷酸三正丁酯、磷酸三(丁氧基乙基)酯、磷酸三(2-乙基己基)酯、(RO)3P=O(R为月桂基、鲸蜡基、硬脂基或油基)等。
作为式(C1-3)所表示的化合物,例如可列举:磷酸二烷基酯(即,R5及R6为烷基的化合物)等。作为磷酸二烷基酯的具体例,可列举:磷酸二丁酯、磷酸双(2-乙基己基)酯等。
式(C1-1)、式(C1-2)及式(C1-3)中,R1、R2、R3、R4、R5及R6也可分别独立地为包含烷基的烃基、包含芳香族环的烃基、包含脂肪族环的烃基的1种以上。烃基可为一部分具有不饱和基团的烃基,也可具有任意的原子或取代基。此时,R1、R2、R3、R4、R5及R6优选为包含烷基的烃基。此外,烃基优选为未经取代的饱和基团。R1、R2、R3、R4、R5及R6优选相同。
作为(C2)亚磷酸酯,可列举:亚磷酸三甲酯、亚磷酸三乙酯、亚磷酸三正丁酯、亚磷酸三(2-乙基己基)酯、亚磷酸三异辛酯、亚磷酸三癸酯、亚磷酸三异癸酯、亚磷酸三(十三烷基)酯、亚磷酸三油醇酯、亚磷酸三硬脂酯、亚磷酸三苯酯、亚磷酸三(壬基苯基)酯、亚磷酸三(2,4-二-叔丁基苯基)酯、亚磷酸苯基二异辛酯、亚磷酸苯基二异癸酯、亚磷酸二苯基单(2-乙基己基)酯、亚磷酸二苯基异辛酯、亚磷酸二苯基单癸酯、亚磷酸二苯基单异癸酯、亚磷酸二苯基单(十三烷基)酯、亚磷酸双(壬基苯基)二壬基苯酯、四苯基二丙二醇二亚磷酸酯、亚磷酸聚(二丙二醇)苯酯、二异癸基季戊四醇二亚磷酸酯、双(十三烷基)季戊四醇二亚磷酸酯、二硬脂基季戊四醇二亚磷酸酯、双(壬基苯基)季戊四醇二亚磷酸酯、四苯基四(十三烷基)季戊四醇四亚磷酸酯、亚磷酸四(十三烷基)-4,4'-亚异丙基二苯酯、三月桂基三硫代亚磷酸酯、二甲基氢亚磷酸酯、二丁基氢亚磷酸酯、二(2-乙基己基)氢亚磷酸酯、二月桂基氢亚磷酸酯、二油基氢亚磷酸酯、二苯基氢亚磷酸酯、亚磷酸二苯基单(2-乙基己基)酯、亚磷酸二苯基单癸酯、及亚磷酸二苯基单(十三烷基)酯等。
(C2)亚磷酸酯优选含有选自由式(C2-1)所表示的化合物、式(C2-2)所表示的化合物、式(C2-3)所表示的化合物、式(C2-4)所表示的化合物、式(C2-5)所表示的化合物及式(C2-6)所表示的化合物所组成的组中的至少一种。
式(C2-1)~式(C2-6)中,R7、R8、R9、R10、R11、R12、R13、R14、R15、R16及R17分别独立地表示任选具有取代基的烃基。
作为R7、R8、R9、R10、R11、R12、R13、R14、R15、R16及R17中的烃基任选具有的取代基,例如可列举:氧烷基等。R7、R8、R9、R10、R11、R12、R13、R14、R15、R16及R17中的烃基优选为未经取代的烃基。
R7、R8、R9、R10、R11、R12、R13、R14、R15、R16及R17中的烃基优选为烷基或芳基,更优选为烷基或苯基,进而优选为烷基。烷基的碳原子数例如也可为1~30,优选为1~18。
式(C2-2)中的R8及R9、式(C2-3)中的R10、R11及R12、式(C2-4)中的R13及R14、及式(C2-5)中的R15及R16优选在各式中彼此相同。
作为式(C2-1)所表示的化合物,例如可列举:亚磷酸单烷基酯(即,R7为烷基的化合物)等。
作为式(C2-2)所表示的化合物,例如可列举:亚磷酸二烷基酯(即,R8及R9为烷基的化合物)等。
作为式(C2-3)所表示的化合物,例如可列举:亚磷酸三烷基酯(即,R10、R11及R12为烷基的化合物)等。此外,作为式(C2-3)所表示的化合物的具体例,可列举:亚磷酸三乙酯、亚磷酸三(2-乙基己基)酯、亚磷酸三癸酯、亚磷酸三月桂酯、亚磷酸三(十三烷基)酯、亚磷酸三油醇酯、亚磷酸二苯基单癸酯等。
作为式(C2-4)所表示的化合物,例如可列举:双(烷基)季戊四醇二亚磷酸酯(即,R13及R14为烷基的化合物)等。此外,作为式(C2-4)所表示的化合物的具体例,可列举:双(癸基)季戊四醇二亚磷酸酯、双(十三烷基)季戊四醇二亚磷酸酯、二硬脂基季戊四醇二亚磷酸酯等。
作为式(C2-5)所表示的化合物,例如可列举:二烷基氢亚磷酸酯(即,R15及R16为烷基的化合物)等。此外,作为式(C2-5)所表示的化合物的具体例,可列举:二乙基氢亚磷酸酯、双(2-乙基己基)氢亚磷酸酯、二月桂基氢亚磷酸酯、二油基氢亚磷酸酯等。
作为式(C2-6)所表示的化合物,例如可列举:单烷基氢亚磷酸酯(即,R17为烷基的化合物)等。此外,作为式(C2-6)所表示的化合物的具体例,可列举:单乙基氢亚磷酸酯、单(2-乙基己基)氢亚磷酸酯、单月桂基氢亚磷酸酯、单油基氢亚磷酸酯等。
式(C2-1)~式(C2-6)中,R7、R8、R9、R10、R11、R12、R13、R14、R15、R16及R17也可分别独立地为包含烷基的烃基、包含芳香族环的烃基、包含脂肪族环的烃基的1种以上。烃基也可为一部分具有不饱和基团的烃基,也可具有任意的原子或取代基。此时,R7、R8、R9、R10、R11、R12、R13、R14、R15、R16及R17优选为包含烷基的烃基。此外,烃基优选为未经取代的饱和基团。R7、R8、R9、R10、R11、R12、R13、R14、R15、R16及R17优选相同。
亚磷酸酯中,优选为选自由亚磷酸三甲酯、亚磷酸三乙酯、亚磷酸三正丁酯、亚磷酸三(2-乙基己基)酯、亚磷酸三异辛酯、亚磷酸三癸酯、亚磷酸三异癸酯、亚磷酸三(十三烷基)酯、亚磷酸三油醇酯、亚磷酸三硬脂酯、亚磷酸三苯酯、亚磷酸三(壬基苯基)酯、亚磷酸二苯基单癸酯等以式(C2-3)所表示的化合物表示的化合物、二异癸基季戊四醇二亚磷酸酯、双(十三烷基)季戊四醇二亚磷酸酯、二硬脂基季戊四醇二亚磷酸酯、双(壬基苯基)季戊四醇二亚磷酸酯、二甲基氢亚磷酸酯、二丁基氢亚磷酸酯、二(2-乙基己基)氢亚磷酸酯、二月桂基氢亚磷酸酯、二油基氢亚磷酸酯所组成的组中的1种以上,更优选为式(C2-3)所表示的化合物。式(C2-3)所表示的化合物中,优选为亚磷酸三甲酯、亚磷酸三乙酯、亚磷酸三正丁酯、亚磷酸三(2-乙基己基)酯、亚磷酸三异辛酯、亚磷酸三癸酯、亚磷酸三异癸酯、亚磷酸三(十三烷基)酯、亚磷酸三油醇酯、亚磷酸三硬脂酯等亚磷酸三烷基酯。亚磷酸三烷基酯中,优选为亚磷酸三癸酯。
(C)磷酸化合物的使用量相对于(A)阳离子聚合性化合物100质量份,优选为0.1~5质量份,更优选为0.02~3质量份。若(C)磷酸化合物的使用量为0.1质量份以上,则可抑制光照射后的粘度的上升,若为5质量份以下,则也没有光固化性变差的情况。
本实施方式的有机电致发光元件用密封剂也可含有光敏剂。所谓光敏剂,是指吸收能量射线而使阳离子自光阳离子聚合引发剂高效率地产生的化合物。
作为光敏剂,并无特别限定,可列举:二苯甲酮衍生物、吩噻嗪衍生物、苯基酮衍生物、萘衍生物、蒽衍生物、菲衍生物、稠四苯衍生物、衍生物、苝衍生物、稠五苯衍生物、吖啶衍生物、苯并噻唑衍生物、苯偶姻衍生物、芴衍生物、萘醌衍生物、蒽醌衍生物、呫吨衍生物、呫吨酮衍生物、噻吨衍生物、噻吨酮衍生物、香豆素衍生物、酮香豆素衍生物、花青衍生物、吖嗪衍生物、噻嗪衍生物、噁嗪衍生物、吲哚啉衍生物、薁衍生物、三烯丙基甲烷衍生物、酞菁衍生物、螺吡喃衍生物、螺噁嗪衍生物、硫代螺吡喃衍生物、有机钌络合物等。这些中,优选为2-羟基-2-甲基-1-苯基-丙烷-1-酮等苯基酮衍生物及/或9,10-二丁氧基蒽等蒽衍生物,更优选为蒽衍生物。蒽衍生物中,优选为9,10-二丁氧基蒽。
关于光敏剂的使用量,就光固化性不变差、储藏稳定性不降低的方面而言,相对于(A)阳离子聚合性化合物100质量份,优选为0.01~10质量份,更优选为0.02~5质量份。
本实施方式的有机电致发光元件用密封剂也可含有硅烷偶联剂。通过含有硅烷偶联剂,本实施方式的光阳离子聚合组合物显示出优异的粘接性或粘接耐久性。
作为硅烷偶联剂,并无特别限定,可列举:γ-氯丙基三甲氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三氯硅烷、乙烯基三乙氧基硅烷、乙烯基-三(β-甲氧基乙氧基)硅烷、γ-(甲基)丙烯酰氧基丙基三甲氧基硅烷、β-(3,4-环氧基环己基)乙基三甲氧基硅烷、γ-缩水甘油醚氧基丙基三甲氧基硅烷、γ-缩水甘油醚氧基丙基三乙氧基硅烷、γ-巯基丙基三甲氧基硅烷、γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三甲氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基甲基二甲氧基硅烷及γ-脲丙基三乙氧基硅烷等。这些硅烷偶联剂也可选择1种以上而使用。这些中,优选选自由β-(3,4-环氧环己基)乙基三甲氧基硅烷、γ-缩水甘油醚氧基丙基三甲氧基硅烷、γ-缩水甘油醚氧基丙基三乙氧基硅烷、γ-(甲基)丙烯酰氧基丙基三甲氧基硅烷所组成的组中的1种以上,更优选为γ-缩水甘油醚氧基丙基三甲氧基硅烷。
关于硅烷偶联剂的使用量,就可获得粘接性或粘接耐久性的方面而言,相对于(A)成分与(B)成分的合计100质量份,优选为0.1~10质量份,更优选为0.2~5质量份。
作为可用于本实施方式的有机电致发光元件用密封剂的固化或粘接的光源,并无特别限定,可列举:卤素灯、金属卤素灯、高功率金属卤素灯(含有铟等)、低压汞灯、高压汞灯、超高压汞灯、氙气灯、氙准分子灯、氙闪光灯、发光二极管(以下,称为LED)等。这些光源就可高效率地进行与各光阳离子聚合引发剂的反应波长相对应的能量射线的照射的方面而言是优选的。
上述光源的各自的辐射波长或能量分布不同。因此,上述光源可根据光阳离子聚合引发剂的反应波长等而适宜选择。此外,自然光(太阳光)也可成为反应引发光源。
作为上述光源的照射,也可进行直接照射、通过反射镜或纤维(fiber)等的聚光照射。也可使用低波长截止滤波器、热射线截止滤波器、冷镜等。
关于本实施方式的有机电致发光元件用密封剂,为了促进光照射后的固化速度,也可进行后加热处理。关于后加热的温度,在用于有机电致发光元件的密封时,就不对有机电致发光元件产生损害的方面而言,优选为150℃以下,更优选为80℃以下。此外,后加热的温度优选为60℃以上。
本实施方式的有机电致发光元件用密封剂也可用作粘接剂。本实施方式的粘接剂可优选地用于有机电致发光元件等的封装体等的粘接。
关于本实施方式的有机电致发光元件用密封剂的制造方法,只要可充分混合上述成分,则并无特别限制。作为各成分的混合方法,并无特别限定,可列举:利用伴随螺旋浆的旋转的搅拌力的搅拌方法、利用通过自转公转的行星式搅拌机等通常的分散机的方法等。这些混合方法就低成本且可进行稳定的混合的方面而言优选。
作为使用本实施方式的有机电致发光元件用密封剂的基材的粘接方法,例如通过具有如下步骤:将有机电致发光元件用密封剂涂布于一个基材的整个面或一部分的步骤;对涂布有上述有机电致发光元件用密封剂的基材的有机电致发光元件用密封剂照射光的步骤;在直至上述被光照射的有机电致发光元件用密封剂固化为止前,在上述一个基材贴合另一个基材的步骤;使通过上述有机电致发光元件用密封剂所贴合的基材固化的步骤,可使基材不暴露于光或热地粘接。
作为使用本实施方式的有机电致发光元件用密封剂而制造有机电致发光显示设备的方法,例如可列举:在一个基板上(背面板)涂布本实施方式的有机电致发光元件用密封剂,对该有机电致发光元件用密封剂照射光而活化后,将光遮断,并经由该组合物将背面板与形成有电致发光元件的基板贴合的方法等。通过该方法,可使有机电致发光元件不暴露于光或热地密封。
可使用如下的方法制造有机电致发光显示设备:使用本实施方式的有机电致发光元件用密封剂,在一个基板上涂布本实施方式的有机电致发光元件用密封剂,经由有机电致发光元件用密封剂,贴合另一个基板,并对本实施方式的有机电致发光元件用密封剂照射光。
本实施方式的有机电致发光元件用密封剂优选照射光起10分钟后的粘度与光照射前的粘度相比不足5倍。作为光,优选为UV。例如,更优选为通过高压汞灯以100mW/cm2照射30秒UV起10分钟后的粘度与UV照射前的粘度相比不足5倍。
本实施方式的有机电致发光元件用密封剂优选(B)光阳离子聚合引发剂吸收所照射的光而激发,其激发种子分解而产生酸。
本实施方式的有机电致发光元件用密封剂的光照射后的粘度的上升较少,可抑制释气的产生,不易使有机电致发光元件劣化。
以上,对本发明的优选实施方式进行了说明,但本发明并不限定于上述实施方式。
例如,本发明的一个方式也可为使上述有机电致发光元件用密封剂固化而成的固化体。
此外,本发明的另一个方式也可为包含上述固化体的有机电致发光元件用密封材料。该密封材料可为固化体,也可为包含密封剂的固化体与其他构成材料者。作为其他构成材料,例如可列举:硅氮化物膜、硅氧化物膜、硅氮化氧化物等无机物层、二氧化硅、云母、高岭土、滑石、铝氧化物等无机填料等。
此外,本发明的进而另一个方式也可为包含有机电致发光元件、与上述有机电致发光元件用密封材料的有机电致发光显示设备。
此外,本发明中,有机电致发光显示设备的制造方法也可具有:在第一构件附着上述有机电致发光元件用密封剂的附着步骤;对所附着的有机电致发光元件用密封剂照射光的照射步骤;借助经光照射的上述有机电致发光元件用密封剂,将第一构件与第二构件贴合的贴合步骤。该制造方法中,例如,第一构件也可为基板,第二构件也可为有机电致发光元件。该制造方法中的各步骤的条件等也可基于上述实施方式的记载而适宜选择。
[实施例]
以下,列举实验例,更详细地说明本实施方式。本实施方式并不限定于此。只要无特别说明,则以23℃、相对湿度50质量%进行试验。
实验例中,使用以下的化合物。
使用下述物质作为(A-1)具有环氧基的脂环式化合物。
(a-1-1)3',4'-环氧环己基甲基-3,4-环氧环己烷羧酸酯(Daicel化学公司制造的“Celloxide 2021P”)
(a-1-2)氢化双酚A型环氧树脂(三菱化学公司制造的“YX8000”,分子量380~430)
(a-1-3)甲基丙烯酸3,4-环氧环己基甲酯(Daicel公司制造的“Cyclomer M100”)
使用下述物质作为(A-2)具有环氧基的芳香族化合物。
(a-2-1)双酚A型环氧树脂(三菱化学公司制造的“jER828”,分子量360~390)
(a-2-2)双酚F型环氧树脂(三菱化学公司制造的“jER806”,分子量320~340)
(a-2-3)双酚F型环氧树脂(三井化学公司制造的“YL983U”,分子量360~380)
(a-2-4)双酚F型环氧树脂(ADEKA公司制造的“KRM-2490”,分子量340~380)
使用下述物质作为其他阳离子聚合性化合物。
(a-3)三丙二醇二缩水甘油醚(共荣社化学公司制造的“Epolight 200P”)
(a-4)二(1-乙基-(3-氧杂环丁基))甲醚(东亚合成公司制造的“ARONE OXETANEOXT-221”)
(a-5)环己烷二甲醇二乙烯醚(Nippon Carbide公司制造的“CHDVE”)
使用下述物质作为(B)成分的光阳离子聚合引发剂。
(b-1)三芳基锍盐六氟锑酸盐(ADEKA公司制造的“AdekaOptomer SP-170”,阴离子种为六氟锑酸盐)
(b-2)三芳基锍盐(二苯基4-硫代苯氧基苯基锍三(五氟乙基)三氟磷酸盐,SAN-APRO公司制造的“CPI-200K”,阴离子种为磷化合物)
使用下述物质作为(C)成分的磷酸酯及/或亚磷酸酯。
(c-1)磷酸三(2-乙基己基)酯(大八化学工业公司制造的“TOP”)
(c-2)亚磷酸三癸酯(城北化学工业公司制造的“JP-310”)
(c-3)双(癸基)季戊四醇二亚磷酸酯(城北化学工业公司制造的“JPE-10”)
(c-4)双(2-乙基己基)氢亚磷酸酯(城北化学工业公司制造的“JPE-208”)
(c-5)亚磷酸二苯基单癸酯(城北化学工业公司制造的“JPM-311”)
(c-6比较例)三正辛基氧化膦(北兴化学工业公司制造的“T.O.P.O(注册商标)”)
(c-7比较例)三正辛基膦(城北化学工业公司制造的“TOCP”)
(c-8比较例)18-冠-6-醚(日本曹达公司制造的“Crown ether O-18”)
使用下述物质作为光敏剂。
(g-1)9,10-二丁氧基蒽(川崎化成工业公司制造的“ANTHRACURE UVS-1331”)
使用下述物质作为硅烷偶联剂。
(f-1)γ-缩水甘油醚氧基丙基三甲氧基硅烷(Shin-Etsu Silicones公司制造的“KBM-403”)
将表1~2所示的种类的原材料以表1~2所示的组成比率进行混合,制备实施例及比较例的有机电致发光元件用密封剂。组成比率的单位为质量份。
对实施例及比较例的有机电致发光元件用密封剂,进行下述的各测定。将其结果示于表1~2。
[粘度]
密封剂的粘度(剪切粘度)使用E型粘度计(1°34'×R24的锥形转子),于温度25℃、转速10rpm的条件下进行测定。
[光照射后的粘度变化]
将实施例及比较例中所获得的各有机电致发光元件用密封剂涂布于玻璃基板上,使用紫外线照射装置(HOYA公司制造的超高压汞灯照射装置,“UL-750”)对该基板照射波长365nm、100mW/cm2的紫外线30秒。于照射紫外线结束起10分钟后,使用E型粘度计(1°34'×R24的锥形转子),于温度25℃、转速10rpm的条件下进行测定。并且,在将光照射前的粘度设为V0、将光照射后的粘度设为Vν时,根据式:Vν/V0求出粘度变化率。粘度变化率就慢固化性良好的方面而言,优选为5以下。
[光固化条件]
在评价密封剂的固化物性及粘接性时,通过下述光照射条件,而使密封剂固化。通过搭载有无电极放电金属卤素灯的UV固化装置(Fusion公司制造),通过365nm的波长的累计光量4,000mJ/cm2的条件,使密封剂光固化后,于80℃的烘箱中,实施30分钟的后加热处理,获得固化体。
[透湿度]
通过上述光固化条件制作厚度0.1mm的片状的固化体,依据JIS Z0208“防湿包装材料的透湿度试验方法(杯法)”,使用氯化钙(无水)作为吸湿剂,以环境温度60℃、相对湿度90%的条件进行测定。透湿度优选为120g/(m2·24hr)以下。
[拉伸剪切粘接强度]
使用两片硼硅酸玻璃试片(纵25mm×横25mm×厚2.0mm,TEMPAX(注册商标)玻璃),以粘接面积0.5cm2、粘接厚度80μm,通过上述的光固化条件而使密封剂固化。固化后,使用利用密封剂所接合的试片,于温度23℃、相对湿度50%的环境下,以拉伸速度10mm/min测定拉伸剪切粘接强度(单位:MPA)。拉伸剪切粘接强度优选为15MPa以上。
[释气量]
将密封剂以每单位面积的涂布量成为10mg/cm2的方式涂布于玻璃基板上,使用紫外线照射装置(HOYA公司制造的超高压汞灯照射装置“UL-750”)对该基板照射波长365nm、100mW/cm2的紫外线10秒。其后,于80℃下加热60分钟,捕获、浓缩所产生的气体成分,利用GC/MS(Agilent Technology公司制造的“GC/MS 7890B/5977B”)测定释气量。释气量优选为60ppm以下。
[有机EL的评价]
[有机EL元件基板的制作]
分别使用丙酮、异丙醇将带ITO电极的玻璃基板洗净。其后,通过真空蒸镀法以成为薄膜的方式依次蒸镀以下的化合物,获得包含阳极/空穴注入层/空穴传输层/发光层/电子注入层/阴极的有机EL元件基板。各层的构成如下所述。
·阳极ITO、阳极的膜厚250nm
·空穴注入层铜酞菁厚度30nm
·空穴传输层N,N'-二苯基-N,N'-二萘基联苯胺(α-NPD)厚度20nm
·电子注入层氟化锂厚度1nm
·阴极铝、阳极的膜厚250nm
[有机EL元件的制作]
将实施例及比较例中所获得的密封剂于氮气环境下通过涂布装置涂布于玻璃,与有机EL元件基板贴合,以粘接厚度10μm并通过上述光固化条件,使该密封剂固化,制作有机EL元件。
[有机EL评价]
[初期]
将刚制作后的有机EL元件于85℃、相对湿度85质量%的条件下暴露1000小时后,施加6V的电压,利用目视与显微镜观察有机EL元件的发光状态,测定暗点的直径。
[高温高湿度]
将刚制作后的有机EL元件于85℃、相对湿度85质量%的条件下暴露1000小时后,施加6V的电压,利用目视与显微镜观察有机EL元件的发光状态,测定暗点的直径。
暗点的直径优选为300μm以下,更优选为50μm以下,最优选为无暗点。
[保存稳定性评价]
测定密封剂的初期粘度(V0,密封剂刚制备后的粘度)后,以放入容器中并盖上盖的状态(密闭体系),利用约40℃的高温环境下的促进试验测定4周后的密封剂的粘度(V4)。并且,根据式:V4/V0求出粘度变化率。粘度变化率就保存稳定性良好的方面而言,优选为1.5以下。
表1
表2
本实施方式的密封剂于光照射时不易产生释气,故而耐久性良好,不使元件劣化。本实施方式以外的密封剂不具有效果。不使用(C)成分时,光照射后的粘度变化较大(实验例15)。使用氧化膦时,密封剂不固化(实验例16)。使用膦时,密封剂凝胶化,不具有本实施方式的效果(实验例17)。使用冠醚时,无法获得高温高湿度下的耐久性(实验例18)。不使用(B)成分时,密封剂不固化(实验例19)。不使用(A-2)成分时,无法获得耐久性(实验例20)。不使用(A-1)成分时,无法获得高温高湿度下的耐久性(实验例21)。
Claims (15)
1.一种有机电致发光元件用密封剂,其含有:(A)阳离子聚合性化合物、(B)光阳离子聚合引发剂、及(C)选自由磷酸酯及亚磷酸酯所组成的组中的一种以上磷酸化合物;且
(A)阳离子聚合性化合物含有(A-1)具有环氧基的脂环式化合物及(A-2)具有环氧基的芳香族化合物。
2.如权利要求1所述的有机电致发光元件用密封剂,其中,(C)磷酸化合物为(C1)磷酸酯。
4.如权利要求1所述的有机电致发光元件用密封剂,其中,(C)磷酸化合物为(C2)亚磷酸酯。
6.如权利要求1至5中任一项所述的有机电致发光元件用密封剂,其中,(A-2)具有环氧基的芳香族化合物为选自由双酚A型环氧树脂、双酚F型环氧树脂所组成的组中的一种以上。
7.如权利要求1至6中任一项所述的有机电致发光元件用密封剂,其中,(B)光阳离子聚合引发剂为鎓盐。
8.如权利要求1至7中任一项所述的有机电致发光元件用密封剂,其中,(B)光阳离子聚合引发剂的使用量相对于(A)阳离子聚合性化合物100质量份,为0.05~5.0质量份。
9.如权利要求1至8中任一项所述的有机电致发光元件用密封剂,其还含有光敏剂。
10.如权利要求1至9中任一项所述的有机电致发光元件用密封剂,其还含有硅烷偶联剂。
11.一种权利要求1至10中任一项所述的有机电致发光元件用密封剂的固化体。
12.一种有机电致发光元件用密封材料,其包含权利要求11所述的固化体。
13.一种有机电致发光显示设备,其包含:
有机电致发光元件、及
权利要求12所述的有机电致发光元件用密封材料。
14.一种有机电致发光显示设备的制造方法,其包括:
附着步骤,其使权利要求1至10中任一项所述的有机电致发光元件用密封剂附着于第一构件;
照射步骤,其对所附着的所述有机电致发光元件用密封剂照射光;及
贴合步骤,其借助经光照射的所述有机电致发光元件用密封剂而将所述第一构件与第二构件贴合。
15.如权利要求14所述的有机电致发光显示设备的制造方法,其中,所述第一构件为基板,
所述第二构件为有机电致发光元件。
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