WO2020171186A1 - 組成物 - Google Patents
組成物 Download PDFInfo
- Publication number
- WO2020171186A1 WO2020171186A1 PCT/JP2020/006922 JP2020006922W WO2020171186A1 WO 2020171186 A1 WO2020171186 A1 WO 2020171186A1 JP 2020006922 W JP2020006922 W JP 2020006922W WO 2020171186 A1 WO2020171186 A1 WO 2020171186A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- group
- formula
- composition
- bisphenol
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 142
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 39
- 150000003014 phosphoric acid esters Chemical class 0.000 claims abstract description 20
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 18
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001334 alicyclic compounds Chemical class 0.000 claims abstract description 15
- 239000003999 initiator Substances 0.000 claims abstract description 14
- 238000012663 cationic photopolymerization Methods 0.000 claims abstract description 13
- 150000003016 phosphoric acids Chemical class 0.000 claims abstract description 6
- -1 phosphate compound Chemical class 0.000 claims description 105
- 239000003822 epoxy resin Substances 0.000 claims description 56
- 229920000647 polyepoxide Polymers 0.000 claims description 56
- 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 52
- 238000005401 electroluminescence Methods 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 36
- 239000004593 Epoxy Substances 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000003505 polymerization initiator Substances 0.000 claims description 25
- 150000002430 hydrocarbons Chemical group 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 229910019142 PO4 Inorganic materials 0.000 claims description 16
- 239000010452 phosphate Substances 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000008393 encapsulating agent Substances 0.000 claims description 9
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000008859 change Effects 0.000 claims description 7
- 239000003504 photosensitizing agent Substances 0.000 claims description 7
- 239000003566 sealing material Substances 0.000 claims description 6
- 230000001678 irradiating effect Effects 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229930185605 Bisphenol Natural products 0.000 claims description 3
- 239000004841 bisphenol A epoxy resin Substances 0.000 abstract 2
- 239000004842 bisphenol F epoxy resin Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 description 36
- 239000000565 sealant Substances 0.000 description 21
- 239000000126 substance Substances 0.000 description 13
- 125000002723 alicyclic group Chemical group 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000000853 adhesive Substances 0.000 description 11
- 230000001070 adhesive effect Effects 0.000 description 11
- 238000001723 curing Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 11
- 238000007789 sealing Methods 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000011521 glass Substances 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
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 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 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001454 anthracenes Chemical class 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 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 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 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
- 238000005259 measurement Methods 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
- 238000000016 photochemical curing Methods 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
- 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
- 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
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MDAMDUOJVXLIDB-UHFFFAOYSA-N C1=CC(O)=CC=C1CSCC(=O)C1=CC=CC=C1 Chemical compound C1=CC(O)=CC=C1CSCC(=O)C1=CC=CC=C1 MDAMDUOJVXLIDB-UHFFFAOYSA-N 0.000 description 3
- RRHPXHKVFHDKRB-UHFFFAOYSA-N C1=CC=CC2=CC(CSCCC(=O)OCC)=CC=C21 Chemical compound C1=CC=CC2=CC(CSCCC(=O)OCC)=CC=C21 RRHPXHKVFHDKRB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 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
- 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 3
- ABKJGHLMKKHLGY-UHFFFAOYSA-N [4-[4-bis[4-(2-hydroxyethoxy)phenyl]sulfoniophenyl]sulfanylphenyl]-bis[4-(2-hydroxyethoxy)phenyl]sulfanium Chemical compound C1=CC(OCCO)=CC=C1[S+](C=1C=CC(SC=2C=CC(=CC=2)[S+](C=2C=CC(OCCO)=CC=2)C=2C=CC(OCCO)=CC=2)=CC=1)C1=CC=C(OCCO)C=C1 ABKJGHLMKKHLGY-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 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 3
- 150000004292 cyclic ethers Chemical group 0.000 description 3
- GLOQRSIADGSLRX-UHFFFAOYSA-N decyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCC)OC1=CC=CC=C1 GLOQRSIADGSLRX-UHFFFAOYSA-N 0.000 description 3
- SPBMDAHKYSRJFO-UHFFFAOYSA-N didodecyl hydrogen phosphite Chemical compound CCCCCCCCCCCCOP(O)OCCCCCCCCCCCC SPBMDAHKYSRJFO-UHFFFAOYSA-N 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
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000002367 halogens 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
- GBHRVZIGDIUCJB-UHFFFAOYSA-N hydrogenphosphite Chemical compound OP([O-])[O-] GBHRVZIGDIUCJB-UHFFFAOYSA-N 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000004010 onium ions Chemical class 0.000 description 3
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 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
- 241000894007 species Species 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
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 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
- DECPGQLXYYCNEZ-UHFFFAOYSA-N tris(6-methylheptyl) phosphite Chemical compound CC(C)CCCCCOP(OCCCCCC(C)C)OCCCCCC(C)C DECPGQLXYYCNEZ-UHFFFAOYSA-N 0.000 description 3
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 3
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 3
- 229960000834 vinyl ether Drugs 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 2
- WAGRICKHSWCAEE-UHFFFAOYSA-N (9-oxo-7-propan-2-ylthioxanthen-2-yl)-diphenylsulfanium Chemical compound C1=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WAGRICKHSWCAEE-UHFFFAOYSA-N 0.000 description 2
- YBQHLCCONMXKNT-UHFFFAOYSA-N (9-oxothioxanthen-2-yl)-diphenylsulfanium Chemical compound C1=C2C(=O)C3=CC=CC=C3SC2=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 YBQHLCCONMXKNT-UHFFFAOYSA-N 0.000 description 2
- 0 *OP1OCC2(COP(*)OC2)CO1 Chemical compound *OP1OCC2(COP(*)OC2)CO1 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
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 2
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 2
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical class CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-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
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 2
- JUXZNIDKDPLYBY-UHFFFAOYSA-N 3-ethyl-3-(phenoxymethyl)oxetane Chemical compound C=1C=CC=CC=1OCC1(CC)COC1 JUXZNIDKDPLYBY-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 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
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 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
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
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- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012945 sealing adhesive Substances 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- BWPNIANVWARHPR-UHFFFAOYSA-N tridecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCOP(O)O BWPNIANVWARHPR-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- AXYQQAVHPAUFQX-UHFFFAOYSA-N tris(2-methylphenyl)sulfanium Chemical compound CC1=CC=CC=C1[S+](C=1C(=CC=CC=1)C)C1=CC=CC=C1C AXYQQAVHPAUFQX-UHFFFAOYSA-N 0.000 description 1
- BINSXQFBKIIQJI-UHFFFAOYSA-N tris(4-hydroxyphenyl)sulfanium;chloride Chemical compound [Cl-].C1=CC(O)=CC=C1[S+](C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 BINSXQFBKIIQJI-UHFFFAOYSA-N 0.000 description 1
- WUKMCKCDYKBLBG-UHFFFAOYSA-N tris(4-methoxyphenyl)sulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WUKMCKCDYKBLBG-UHFFFAOYSA-N 0.000 description 1
- JZNDMMGBXUYFNQ-UHFFFAOYSA-N tris(dodecylsulfanyl)phosphane Chemical compound CCCCCCCCCCCCSP(SCCCCCCCCCCCC)SCCCCCCCCCCCC JZNDMMGBXUYFNQ-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- 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
-
- 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
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
-
- H—ELECTRICITY
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- 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 composition, a sealant for an organic electroluminescence element, a cured product, a sealing material for an organic electroluminescence element, an organic electroluminescence display device, and a method for manufacturing an organic electroluminescence display device.
- organic electroluminescence (organic EL) display elements and organic thin film solar cell elements have been advanced. Since the organic thin film element can be easily manufactured by vacuum vapor deposition, solution coating, etc., it has excellent productivity.
- the organic electroluminescence 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. Electrons are injected into this organic light emitting material layer from one electrode and holes are injected from the other electrode, so that electrons and holes are combined in the organic light emitting material layer to perform self-light emission.
- the organic electroluminescence display element has advantages that it has good visibility, can be made thinner, and can be driven at a low DC voltage, as compared with a liquid crystal display element that requires a backlight.
- an organic electroluminescence display element has a problem that when the organic light emitting material layer and the electrodes are exposed to the outside air, the light emitting characteristics thereof are rapidly deteriorated and the life is shortened. Therefore, for the purpose of improving the stability and durability of the organic electroluminescence display element, in the organic electroluminescence 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. Has become.
- Patent Document 1 discloses a method of filling a photocurable sealant between organic electroluminescence display element substrates in a top emission organic electroluminescence display element or the like, and irradiating with light to perform sealing. .. However, Patent Document 1 does not describe the encapsulant for organic electroluminescent elements of the present invention.
- Patent Document 2 discloses a UV curable resin composition that can secure a sufficient pot life without using a reactivity control agent as a delayed curing agent. However, there is a problem that the pot life after light irradiation is short. Patent Document 2 does not describe an alicyclic compound having an epoxy group. Patent Document 2 merely exemplifies a phosphoric acid ester as a photocationic polymerization initiator, and does not use it in Examples, and does not use phosphoric acid ester in order to suppress an increase in viscosity after light irradiation.
- Patent Document 3 contains an epoxy resin (excluding "a polyalkylene oxide-added bisphenol derivative having an epoxy group at the terminal"), a photocationic polymerization initiator, and a polyalkylene oxide-added bisphenol derivative having an epoxy group at the terminal.
- a curing reaction is initiated by light irradiation, an organic electroluminescent element sealing adhesive characterized in that it comprises a photo-cationic polymerizable adhesive in which the curing reaction proceeds by a dark reaction even after blocking the light is disclosed.
- Patent Document 3 does not describe an alicyclic compound having an epoxy group.
- Patent Document 3 has a problem that outgas is generated at the time of light irradiation to deteriorate the element.
- Patent Document 4 discloses a sealant for an organic electroluminescence display device, which contains a specific cationically polymerizable compound and a photocationic polymerization initiator.
- Patent Document 4 merely exemplifies the phosphoric acid ester as a photocationic polymerization initiator, and is not used in the examples, and the phosphoric acid ester is not used for suppressing an increase in viscosity after light irradiation.
- Patent Document 5 contains 100 parts by mass of a cationic photopolymerizable compound, 0.1 to 30 parts by mass of a cationic photopolymerization initiator, and 0.1 to 30 parts by mass of a curing control agent composed of a compound having an ether bond.
- a method for sealing an organic electroluminescent device with a post-curing composition in which a control agent has a compound having an ether bond is disclosed.
- such a sealing method has a problem that outgas may be generated at the time of light irradiation to deteriorate the device.
- Patent Document 5 does not describe an alicyclic compound having an epoxy group.
- Patent Document 5 merely exemplifies the phosphoric acid ester as a photocationic polymerization initiator, and is not used in the examples, and the phosphoric acid ester is not used for suppressing an increase in viscosity after light irradiation.
- Patent Document 6 discloses an adduct (A) of a bisphenol A type epoxy resin and at least one phosphoric acid having active hydrogen, a compound (B) having two or more alicyclic epoxy groups, and a cationic light
- An ultraviolet curable resin composition containing a polymerization initiator (C) is disclosed.
- a resin composition using (A) has a problem that the production method of (A) is complicated and outgas is generated by a by-product to deteriorate the element.
- Patent Document 6 does not describe a sealing agent for an organic electroluminescence element.
- Patent Document 7 discloses a radiation-curable composition containing a radiation-curable component and at least two flame retardants belonging to different compound groups. However, Patent Document 7 is a flame-retardant curable composition used for other purposes in the first place, and there is no description about the pot life after light irradiation and the generation of outgas during light irradiation. Patent Document 7 does not describe a sealant for an organic electroluminescence element.
- Patent Document 8 discloses a sealant for an organic electroluminescence display device, which contains a cationically polymerizable compound and a photocationic polymerization initiator, wherein the cationically polymerizable compound is a compound represented by a specific structure. Disclosed is a sealant for organic electroluminescence display elements, which is characterized by containing. Patent Document 8 merely exemplifies a phosphoric acid ester as a photocationic polymerization initiator, and is not used in Examples, and the phosphoric acid ester is not used for suppressing an increase in viscosity after light irradiation.
- Patent Document 9 discloses a sealing agent for sealing the light extraction direction of a top emission type organic electroluminescence element containing a photopolymerizable compound and a photocationic polymerization initiator, wherein The compound is composed of 20 to 80 parts by weight of an epoxy compound having an aliphatic cyclic skeleton and 80 to 20 parts by weight of a bisphenol F type epoxy resin with respect to 100 parts by weight of the photopolymerizable compound.
- a sealant for an organic electroluminescence device which has a total light transmittance of 80% or more for light in the range of 380 to 800 nm.
- Patent Document 9 merely exemplifies the phosphoric acid ester as a photocationic polymerization initiator, and is not used in the examples, and the phosphoric acid ester is not used for suppressing an increase in viscosity after light irradiation.
- Patent Document 10 is composed of an alicyclic epoxy compound (A) having a cycloaliphatic skeleton and two or more epoxy groups in the molecule, silica (B), and a phosphite ester (C).
- a liquid curable epoxy resin composition is disclosed.
- Patent Document 10 merely exemplifies an aromatic epoxy compound having a bisphenol structure as a reactive diluent, and does not use it in Examples. Do not use it in order to suppress the rise or make the organic electroluminescence element less likely to deteriorate.
- JP 2001-357973 A Japanese Patent No. 5919574 Japanese Patent No. 4800247 JP, 2016-58273, A Japanese Patent No. 4384509 Japanese Patent Laid-Open No. 7-247342 Japanese Patent Publication No. 2007-513234 JP, 2016-58273, A JP, 2009-79230, A JP 2012-116935A
- the present invention has been made in view of the above circumstances, has a small increase in viscosity after light irradiation, can be suitably used as a sealant for an organic electroluminescent element, and provides a composition that is less likely to deteriorate the organic electroluminescent element.
- the purpose is to
- the present invention is as follows. ⁇ 1> (A) a cationically polymerizable compound, (B) a photocationic polymerization initiator, and (C) one or more phosphoric acid compounds selected from the group consisting of phosphoric acid esters and phosphorous acid esters.
- the (A) cationically polymerizable compound contains (A-1) an alicyclic compound having an epoxy group and (A-2) an aromatic compound having an epoxy group, (A-2)
- the aromatic compound having an epoxy group contains (A-2-1) bisphenol A type epoxy resin and (A-2-2) bisphenol F type epoxy resin, (A-2-1) a bisphenol A type epoxy resin content A 1 and (A-2-2) a bisphenol F-type ratio A 1 / A 2 between the content A 2 of epoxy resin (weight ratio), 0 A composition that is between 2 and 5.
- (C1) phosphate is selected from the group consisting of a compound represented by the formula (C1-1), a compound represented by the formula (C1-2) and a compound represented by the formula (C1-3)
- the composition according to ⁇ 2> which contains at least one selected.
- R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrocarbon group which may have a substituent.
- ⁇ 4> The composition according to ⁇ 1>, wherein the (C) phosphoric acid compound is a (C2) phosphorous acid ester.
- phosphite is a compound represented by the formula (C2-1), a compound represented by the formula (C2-2), a compound represented by the formula (C2-3), a formula ( ⁇ 4>, containing at least one selected from the group consisting of a compound represented by C2-4), a compound represented by formula (C2-5) and a compound represented by formula (C2-6) Composition.
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are carbon atoms each optionally having a substituent. Indicates a hydrogen group.
- the amount of the phosphoric acid compound (C) used is 0.1 to 5 parts by mass relative to 100 parts by mass of the (A) cationically polymerizable compound, according to any one of ⁇ 1> to ⁇ 5>.
- the composition as described. ⁇ 7> The composition according to any one of ⁇ 1> to ⁇ 6>, in which the cationic photopolymerization initiator (B) is an onium salt. ⁇ 8> Any of ⁇ 1> to ⁇ 7>, in which the content of the (B) photocationic polymerization initiator is 0.05 to 5.0 parts by mass relative to 100 parts by mass of the (A) cationically polymerizable compound.
- ⁇ 10> The composition according to any one of ⁇ 1> to ⁇ 9>, further containing a silane coupling agent.
- a sealant for an organic electroluminescence device containing the composition according to any one of ⁇ 1> to ⁇ 10>.
- ⁇ 12> A cured product of the composition according to any one of ⁇ 1> to ⁇ 10>.
- ⁇ 13> A sealing material for an organic electroluminescence device, containing the cured product according to ⁇ 12>.
- An organic electroluminescence display device including the organic electroluminescence element and the organic electroluminescence element sealing material according to ⁇ 13>.
- ⁇ 15> An attaching step of attaching the composition according to any one of ⁇ 1> to ⁇ 10> to the first member, an irradiation step of irradiating the attached composition with light, and a light irradiation. And a bonding step of bonding the first member and the second member via the composition described above.
- ⁇ 16> The method for manufacturing an organic electroluminescence display device according to ⁇ 15>, wherein the first member is a substrate and the second member is an organic electroluminescence element.
- the (A) cationically polymerizable compound contains (A-1) an alicyclic compound having an epoxy group and (A-2) an aromatic compound having an epoxy group, (A-2)
- the aromatic compound having an epoxy group contains an aromatic epoxy compound having a bisphenol structure
- a composition in which the diameter of the dark spot under high temperature and high humidity conditions is 150 ⁇ m or less after 1000 hours of exposure under conditions of a temperature of 85° C. and a relative humidity of 85% by mass, and after applying a voltage of 6 V for 10 seconds. ..
- composition which has a small increase in viscosity after irradiation with light, can be suitably used as a sealant for an organic electroluminescence element, and is less likely to deteriorate the organic electroluminescence element.
- composition according to the present embodiment (A) cationically polymerizable compound, It is characterized by containing (B) a cationic photopolymerization initiator and (C) at least one phosphoric acid compound selected from the group consisting of phosphoric acid esters and phosphorous acid esters.
- the cationically polymerizable compound contains (A-1) an alicyclic compound having an epoxy group, and (A-2) an aromatic compound having an epoxy group. It is characterized by The composition according to the present embodiment can be suitably used as a sealant for an organic electroluminescence element.
- composition according to the present embodiment contains (A) a cationic polymerizable compound as an essential component.
- the (A) cationically polymerizable compound is preferably photopolymerizable.
- the (A) cationically polymerizable compound contains (A-1) an alicyclic compound having an epoxy group and (A-2) an aromatic compound having an epoxy group. Thereby, good adhesiveness and low moisture permeability can be obtained.
- (A-1) Epoxy group-containing alicyclic compound
- the alicyclic compound having an epoxy group hereinafter, also referred to as alicyclic epoxy compound
- at least one cycloalkane ring for example, cyclohexene) Ring, cyclopentene ring, pinene ring, etc.
- an appropriate oxidizing agent such as hydrogen peroxide, peracid, or an aromatic epoxy compound (for example, bisphenol A type)
- Hydrogenated epoxy compounds and the like obtained by hydrogenating an epoxy resin, a bisphenol F type epoxy resin and the like).
- One or more of these compounds may be selected and used.
- Examples of the alicyclic epoxy compound include 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate and 3,4-epoxycyclohexylalkyl (meth)acrylate (for example, 3,4-epoxycyclohexylmethyl (meth ) Acrylate, etc.), (3,3′,4,4′-diepoxy)bicyclohexyl, hydrogenated bisphenol A type epoxy resin, hydrogenated bisphenol F type epoxy resin and the like.
- alicyclic epoxy compounds alicyclic epoxy compounds having a 1,2-epoxycyclohexane structure are preferable.
- compounds represented by the following formula (A1-1) are preferable.
- X represents a single bond or a linking group (a divalent group having one or more atoms), and the linking group is a divalent hydrocarbon group, a carbonyl group, an ether bond or an ester bond. , A carbonate group, an amide bond, or a group in which a plurality of these are linked)
- X is preferably a linking group.
- the linking groups a functional group having an ester bond is preferable.
- 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate is preferable.
- the molecular weight of the alicyclic epoxy compound is preferably 450 or less, more preferably 400 or less, further preferably less than 300, and further preferably 100 to 280.
- the alicyclic epoxy compound When the alicyclic epoxy compound has a molecular weight distribution, the alicyclic epoxy compound preferably has a number average molecular weight within the above range.
- a number average molecular weight shows the value of polystyrene conversion measured by the following measurement conditions by gel permeation chromatography (GPC).
- GPC gel permeation chromatography
- aromatic compound having an epoxy group any of a monomer, an oligomer and a polymer can be used, and bisphenol A type Epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, biphenyl type epoxy resin, naphthalene type epoxy resin, fluorene type epoxy resin, novolac phenol type epoxy resin, cresol novolac type epoxy resin, modified products thereof, and the like. ..
- One or more of these epoxy resins may be selected and used.
- aromatic epoxy compounds having a bisphenol structure are preferable.
- the aromatic epoxy compounds having a bisphenol structure the compound represented by the following formula (A2-1) is preferable.
- n represents a real number of 0 to 30, and R 21 , R 22 , R 23 and R 24 each independently represent a hydrogen atom or a substituted or unsubstituted carbon atom having 1 to 5 carbon atoms. Represents an alkyl group.
- R 21 , R 22 , R 23 , and R 24 are preferably a hydrogen atom or a methyl group.
- R 21 , R 22 , R 23 , and R 24 are preferably the same.
- n is preferably a real number of 0.1 to 30.
- the aromatic epoxy compounds having a bisphenol structure at least one selected from the group consisting of bisphenol A type epoxy resins and bisphenol F type epoxy resins is preferable.
- the (A-2) aromatic compound having an epoxy group preferably contains (A-2-1) bisphenol A type epoxy resin and (A-2-2) bisphenol F type epoxy resin.
- the bisphenol A type epoxy resin is, for example, an epoxy resin in which R 21 , R 22 , R 23 and R 24 in the formula (A2-1) are methyl groups. Good.
- the bisphenol A type epoxy resin refers to, for example, one obtained by condensing bisphenol A and epichlorohydrin in the presence of an alkali catalyst. Further, a modified epoxy resin obtained by reacting a vegetable oil/fat fatty acid or a modifier with the epoxy group or hydroxyl group of the bisphenol A type epoxy resin may be used.
- the hydrogenated epoxy compound obtained by hydrogenating the bisphenol A type epoxy resin (for example, hydrogenated bisphenol A type epoxy resin corresponding to the above alicyclic epoxy compound) is not included in the bisphenol A type epoxy resin.
- the bisphenol F type epoxy resin is, for example, an epoxy resin in which R 21 , R 22 , R 23 and R 24 in the formula (A2-1) are hydrogen atoms. Good.
- the bisphenol F type epoxy resin refers to, for example, one obtained by condensing bisphenol F and epichlorohydrin in the presence of an alkali catalyst. Further, a modified epoxy resin obtained by reacting a vegetable oil/fat fatty acid or a modifier with the epoxy group or hydroxyl group of the bisphenol F type epoxy resin may be used.
- the hydrogenated epoxy compound obtained by hydrogenating the bisphenol F type epoxy resin (for example, hydrogenated bisphenol F type epoxy resin corresponding to the above-mentioned alicyclic epoxy compound) is not included in the bisphenol F type epoxy resin.
- the molecular weight of the aromatic epoxy compound is preferably 100 to 5,000 in terms of moisture permeability, 150 to 1000 are more preferable, and 200 to 450 are the most preferable.
- the number average molecular weight of the aromatic epoxy compound is preferably within the above range.
- a number average molecular weight shows the value of polystyrene conversion measured by gel permeation chromatography (GPC) on the above-mentioned measurement conditions.
- any of a monomer, an oligomer and a polymer can be used.
- the (A) cationically polymerizable compound of the present embodiment is preferably an epoxy compound.
- the (A) cationically polymerizable compound of the present embodiment preferably has two or more cationically polymerizable groups such as a cyclic ether group and a cationically polymerizable vinyl group, and more preferably has two.
- a cationically polymerizable compound other than (A-1) and (A-2) can be further used.
- examples of other cationically polymerizable compounds other than (A-1) and (A-2) include cyclic ethers and cationically polymerizable vinyl compounds.
- Examples of cyclic ethers include compounds such as epoxy and oxetane.
- the content of the other cationically polymerizable compound other than (A-1) and (A-2) is preferably 40 parts by mass or less, more preferably 20 parts by mass or less. Most preferably, it is 10 parts by mass or less.
- the content of the cationically polymerizable compound other than (A-1) and (A-2) in 100 parts by mass of the (A) cationically polymerizable compound may be, for example, 1 part by mass or more, and 5 parts by mass or more. Or 0 parts by mass.
- Examples of cationically polymerizable vinyl compounds include vinyl ether, vinyl amine, styrene and the like. One or more of these compounds or derivatives may be selected and used.
- one or more kinds of diglycidyl ether compounds, oxetane compounds and vinyl ether compounds are preferable.
- Examples of the diglycidyl ether compound include diglycidyl ether of alkylene glycol (eg, diglycidyl ether of ethylene glycol, diglycidyl ether of propylene glycol, diglycidyl ether of 1,6-hexanediol, etc.), polyglycidyl ether of polyhydric alcohol.
- alkylene glycol eg, diglycidyl ether of ethylene glycol, diglycidyl ether of propylene glycol, diglycidyl ether of 1,6-hexanediol, etc.
- polyglycidyl ether of polyhydric alcohol eg, polyglycidyl ether of polyhydric alcohol.
- di- or triglycidyl ether of glycerin or its alkylene oxide adduct diglycidyl ether of polyalkylene glycol (for example, diglycidyl ether of polyethylene glycol or its alkylene oxide adduct, polypropylene glycol or its alkylene oxide adduct) Diglycidyl ether, etc.).
- examples of the alkylene oxide include aliphatic compounds such as ethylene oxide and propylene oxide.
- the oxetane compound is not particularly limited, but 3-ethyl-3-hydroxymethyl oxetane (trade name: Aron oxetane OXT-101 manufactured by Toagosei Co., Ltd.), 1,4-bis[(3-ethyl-3-oxetanyl) )Methoxymethyl]benzene (the same OXT-121 etc.), 3-ethyl-3-(phenoxymethyl)oxetane (the same OXT-211, etc.), di(1-ethyl-(3-oxetanyl))methyl ether (the same OXT- 221), 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane (the same OXT-212 etc.) and the like.
- the oxetane compound refers to a compound having one or more oxetane rings in the molecule.
- the vinyl ether compound is not particularly limited, ethylene glycol divinyl ether, ethylene glycol monovinyl ether, diethylene glycol divinyl ether, triethylene glycol monovinyl ether, triethylene glycol divinyl ether, propylene glycol divinyl ether, dipropylene glycol divinyl ether, butanediol divinyl ether.
- Di- or trivinyl ether compounds such as vinyl ether, hexanediol divinyl ether, cyclohexanedimethanol divinyl ether, hydroxyethyl monovinyl ether, hydroxynonyl monovinyl ether, trimethylolpropane trivinyl ether, ethyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, octadecyl vinyl ether, Monovinyl ether compounds such as cyclohexyl vinyl ether, hydroxybutyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexane dimethanol monovinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, isopropenyl ether o-propylene carbonate, dodecyl vinyl ether, diethylene glycol monovinyl ether, octadecyl vinyl ether
- the amount of the (A-1) epoxy group-containing alicyclic compound used is preferably 30 to 95 parts by mass, more preferably 50 to 90 parts by mass, and 60 to 80 parts by mass based on 100 parts by mass of the (A) cationically polymerizable compound. Most preferred is parts by weight, and even more preferred is 65 to 75 parts by weight. This tends to improve the durability of the cured body.
- the amount of the (A-2) aromatic compound having an epoxy group to be used is preferably 5 to 70 parts by mass, more preferably 10 to 50 parts by mass, and 20 to 40 parts by mass, relative to 100 parts by mass of the (A) cationically polymerizable compound. Parts are most preferred and 25 to 35 parts by weight are even more preferred. This tends to improve the durability of the cured body.
- the total content of the (A-1) epoxy group-containing alicyclic compound and (A-2) epoxy group-containing aromatic compound is 60 parts by mass or more. It is more preferably 80 parts by mass or more, most preferably 90 parts by mass or more, and even more preferably 100 parts by mass.
- composition according to the present embodiment contains (B) a photocationic polymerization initiator as an essential component.
- a photocationic polymerization initiator When the photocationic polymerization initiator is used, the composition of the present embodiment can be cured by irradiation with energy rays such as ultraviolet rays.
- the cationic photopolymerization initiator (B) is not particularly limited, but arylsulfonium salt derivatives (for example, Cylacure UVI-6990, Cylacure UVI-6974 manufactured by Dow Chemical Co., Ltd., and ADEKA OPTOMER SP-150 manufactured by Asahi Denka Co., Ltd.) are used. , Adeka Optomer SP-152, Adeka Optomer SP-170, Adeka Optomer SP-172, CPI-100P, CPI-101A, CPI-200K, CPI-210S, LW-S1, manufactured by Double Bond Co.
- arylsulfonium salt derivatives for example, Cylacure UVI-6990, Cylacure UVI-6974 manufactured by Dow Chemical Co., Ltd., and ADEKA OPTOMER SP-150 manufactured by Asahi Denka Co., Ltd.
- Ciba Cure 1190 aryliodonium salt derivatives (eg, Ciba Specialty Chemicals Irgacure 250, Rhodia Japan RP-2074), allene-ion complex derivatives, diazonium salt derivatives, triazine initiators and others. Acid generators such as halides and the like.
- an onium salt represented by the formula (B-1) is preferable.
- the cationic photopolymerization initiator (B) is not particularly limited, and examples thereof include onium salts represented by the formula (B-1).
- (A represents an element having a valence of m of Group VIIA to Group VIIA.
- m represents 1 to 2.
- p represents 0 to 3.
- R represents an organic group bonded to A.
- D is the following formula (B-1-1): Represents a divalent group represented by.
- E represents a divalent group
- G represents —O—, —S—, —SO—, —SO 2 —, —NH—, —NR′—, —CO—.
- a represents 0 to 5.
- a+1 E and a G may be the same or different.
- a is preferably an integer.
- X ⁇ is a counter ion of onium, and the number thereof is p+1 per molecule.
- the onium ion of the formula (B-1) is not particularly limited, but includes 4-(phenylthio)phenyldiphenylsulfonium, bis[4-(diphenylsulfonio)phenyl]sulfide, bis[4- ⁇ bis[4-(2-hydroxy Ethoxy)phenyl]sulfonio ⁇ phenyl]sulfide, bis ⁇ 4-[bis(4-fluorophenyl)sulfonio]phenyl ⁇ sulfide, 4-(4-benzoyl-2-chlorophenylthio)phenylbis(4-fluorophenyl)sulfonium, 4-(4-benzoylphenylthio)phenyldiphenylsulfonium, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracen-2-yldi-p-tolylsulfonium, 7-isopropyl-9
- R is an organic group bonded to A.
- R is, for example, an aryl group having 6 to 30 carbon atoms, a heterocyclic group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an alkynyl group having 2 to 30 carbon atoms.
- alkyl hydroxy, alkoxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, arylthiocarbonyl, acyloxy, arylthio, alkylthio, aryl, heterocycle, aryloxy, alkylsulfinyl, arylsulfinyl, alkylsulfonyl. It may be substituted with at least one selected from the group consisting of arylsulfonyl, alkyleneoxy, amino, cyano and nitro groups and halogen.
- the number of Rs is m+p(m-1)+1, which may be the same as or different from each other.
- two or more Rs are directly or mutually —O—, —S—, —SO—, —SO 2 —, —NH—, —NR′—, —CO—, —COO—, —CONH—, carbon number. They may be bonded via 1 to 3 alkylene or phenylene groups to form a ring structure containing the element A.
- R′ is an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 10 carbon atoms.
- aryl group having 6 to 30 carbon atoms a condensed monocyclic aryl group such as phenyl group and naphthyl, anthracenyl, phenanthrenyl, pyrenyl, chrysenyl, naphthacenyl, benzanthracenyl, anthraquinolyl, fluorenyl, naphthoquinone, anthraquinone Examples include polycyclic aryl groups.
- the aryl group having 6 to 30 carbon atoms, the heterocyclic group having 4 to 30 carbon atoms, the alkyl group having 1 to 30 carbon atoms, the alkenyl group having 2 to 30 carbon atoms or the alkynyl group having 2 to 30 carbon atoms is at least 1 It may have various kinds of substituents, and examples of the substituents include straight-chain alkyl having 1 to 18 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl and octadecyl.
- a linear or branched acyloxy group having 2 to 19 carbon atoms such as oxy, octylcarbonyloxy, tetradecylcarbonyloxy, octadecylcarbonyloxy; phenylthio, 2-methylphenyl Phenylthio, 3-methylphenylthio, 4-methylphenylthio, 2-chlorophenylthio, 3-chlorophenylthio, 4-chlorophenylthio, 2-bromophenylthio, 3-bromophenylthio, 4-bromophenylthio, 2-fluoro Phenylthio, 3-fluorophenylthio, 4-fluorophenylthio, 2-hydroxyphenylthio, 4-hydroxyphenylthio, 2-methoxyphenylthio, 4-methoxyphenylthio, 1-naphthylthio, 2-naphthylthio, 4-[ 4-(phenylthio
- alkylsulfinyl group 1-18 linear or branched alkylsulfinyl group; arylsulfinyl group having 6-10 carbon atoms such as phenylsulfinyl, tolylsulfinyl, naphthylsulfinyl; methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl , Sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl, isopentylsulfonyl, neopentylsulfonyl, tert-pentylsulfonyl, octylsulfonyl, etc., straight-chain or branched alkylsulfon
- p represents the number of repeating units of [DA + R m-1 ] bond, and is preferably an integer of 0 to 3.
- Preferred as the onium ion [A + ] in the formula (B-1) are sulfonium, iodonium and selenium, and typical examples thereof include the following.
- sulfonium ion examples include triphenylsulfonium, tri-p-tolylsulfonium, tri-o-tolylsulfonium, tris(4-methoxyphenyl)sulfonium, 1-naphthyldiphenylsulfonium, 2-naphthyldiphenylsulfonium, and tris(4-fluorophenyl).
- sulfonium ions one or more kinds of sulfonium ions and iodonium ions are preferable, and sulfonium ions are more preferable.
- the sulfonium ion include triphenylsulfonium, tri-p-tolylsulfonium, 4-(phenylthio)phenyldiphenylsulfonium, bis[4-(diphenylsulfonio)phenyl]sulfide, bis[4- ⁇ bis[4-(2- Hydroxyethoxy)phenyl]sulfonio ⁇ phenyl]sulfide, bis ⁇ 4-[bis(4-fluorophenyl)sulfonio]phenyl ⁇ sulfide, 4-(4-benzoyl-2-chlorophenylthio)phenylbis(4-fluorophenyl)sulfonium , 4-(4-benzoylphenylthio)pheny
- X ⁇ is a counter ion.
- the number is p+1 per molecule.
- the counter ion is not particularly limited, but examples thereof include boron compounds, phosphorus compounds, antimony compounds, arsenic compounds, halides such as alkyl sulfonic acid compounds, and methide compounds.
- Examples of X ⁇ include halogen ions such as F ⁇ , Cl ⁇ , Br ⁇ , and I ⁇ ; OH ⁇ ; ClO 4 ⁇ ; FSO 3 ⁇ , ClSO 3 ⁇ , CH 3 SO 3 ⁇ , C 6 H 5 SO 3 Sulfonate ions such as -- , CF 3 SO 3 -- , Sulfate ions such as HSO 4 -- , SO 4 2 -- , Carbonate ions such as HCO 3 -- , CO 3 2 -- , H 2 PO 4 -- , HPO 4 2- , PO 4 3-, etc.
- halogen ions such as F ⁇ , Cl ⁇ , Br ⁇ , and I ⁇ ; OH ⁇ ; ClO 4 ⁇ ; FSO 3 ⁇ , ClSO 3 ⁇ , CH 3 SO 3 ⁇ , C 6 H 5 SO 3 Sulfonate ions such as -- , CF 3 SO 3 -- , Sulfate ions such as HSO
- phosphate ions such as fluorinated alkylfluorophosphate ions; BF 4 ⁇ , B(C 6 F 5 ) 4 And borate ions such as B(C 6 H 4 CF 3 ) 4 ⁇ ; AlCl 4 ⁇ ; BiF 6 ⁇ and the like.
- fluoroantimonate ions such as SbF 6 ⁇ and SbF 5 OH ⁇
- fluoroarsenate ions such as AsF 6 ⁇ and AsF 5 OH ⁇ .
- fluorinated alkylfluorophosphate ion examples include the fluorinated alkylfluorophosphate ion represented by the formula (B-1-3) and the like.
- Rf represents an alkyl group substituted with a fluorine atom.
- the number b of Rf is 1 to 5, and is preferably an integer.
- the b Rf's may be the same or different.
- the number b of Rf is more preferably 2 to 4, and most preferably 2 to 3.
- Rf represents an alkyl group substituted with a fluorine atom, preferably having 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms. Is.
- alkyl group examples include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl and octyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl and tert-butyl; and further cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. And the like.
- preferable fluorinated alkylfluorophosphate anions include [(CF 3 CF 2 ) 2 PF 4 ] - , [(CF 3 CF 2 ) 3 PF 3 ] - , and [((CF 3 ) 2 CF) 2 PF 4 ] ⁇ , [((CF 3 ) 2 CF) 3 PF 3 ] ⁇ , [(CF 3 CF 2 CF 2 ) 2 PF 4 ] ⁇ , [(CF 3 CF 2 CF 2 ) 3 PF 3 ] ⁇ , [((CF 3) 2 CFCF 2) 2 PF 4] -, [((CF 3) 2 CFCF 2) 3 PF 3] -, [(CF 3 CF 2 CF 2 CF 2) 2 PF 4] - and [ (CF 3 CF 2 CF 2 CF 2 ) 3 PF 3 ] - and the like.
- the cationic photopolymerization initiator may be dissolved in a solvent in advance so that it can be easily dissolved in an epoxy compound or an epoxy resin.
- the solvent include carbonates such as propylene carbonate, ethylene carbonate, 1,2-butylene carbonate, dimethyl carbonate and diethyl carbonate.
- One or more of these photocationic polymerization initiators may be selected and used.
- anionic species of the (B) photocationic polymerization initiator include halides such as boron compounds, phosphorus compounds, antimony compounds, arsenic compounds, and alkylsulfonic acid compounds.
- halides such as boron compounds, phosphorus compounds, antimony compounds, arsenic compounds, and alkylsulfonic acid compounds.
- fluorides are preferable because they are excellent in photocurability and have improved adhesiveness and adhesive durability. Of the fluorides, hexafluoroantimonate is preferred.
- triarylsulfonium salt hexafluoroantimonate represented by the formula (B-2) and diphenyl 4-thiophenoxyphenylsulfonium tris( represented by the formula (B-3) One or more of pentafluoroethyl)trifluorophosphate is preferable, and triarylsulfonium salt hexafluoroantimonate is more preferable.
- the amount of the (B) photocationic polymerization initiator used is preferably 0.05 to 5 parts by mass, and more preferably 0.1 to 3 parts by mass, relative to 100 parts by mass of the (A) cationically polymerizable compound.
- the amount of the cationic photopolymerization initiator used is 0.05 parts by mass or more, the photocurability tends to be improved, and when it is 5 parts by mass or less, the adhesion durability tends to be further improved.
- the composition according to the present embodiment contains (C) a phosphoric acid compound as an essential component.
- the phosphoric acid compound is one or more selected from the group consisting of (C1) phosphoric acid ester and (C2) phosphorous acid ester.
- the phosphoric acid compound is preferably an organic phosphoric acid compound. Among the phosphoric acid compounds, (C1) phosphoric acid ester is preferable.
- the (C1) phosphate ester is selected from the group consisting of a compound represented by the formula (C1-1), a compound represented by the formula (C1-2) and a compound represented by the formula (C1-3). It is preferable to contain at least one kind, and it is more preferable to contain the compound represented by the formula (C1-2).
- R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently have a substituent. Represents a good hydrocarbon group.
- R 2 , R 3 and R 4 in the formula (C1-2) and R 5 and R 6 in the formula (C1-3) are preferably the same groups in each formula.
- Examples of the substituent that the hydrocarbon group in R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may have include an oxyalkyl group and the like.
- the hydrocarbon group for R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is preferably an unsubstituted hydrocarbon group.
- the hydrocarbon group for R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is preferably an alkyl group or an aryl group, more preferably an alkyl group or a phenyl group, and an alkyl group. More preferably.
- the number of carbon atoms in the alkyl group may be, for example, 1 to 18, preferably 4 to 13.
- the compound represented by the formula (C1-1) may be, for example, monoalkyl phosphate (that is, a compound in which R 1 is an alkyl group), and specific examples include monoethyl phosphate and mono n-butyl. Examples thereof include phosphate, mono(butoxyethyl)phosphate, mono(2-ethylhexyl)phosphate and the like.
- a trialkyl phosphate that is, a compound in which R 2 , R 3 and R 4 are alkyl groups
- the number of carbon atoms of the alkyl group of R 2 , R 3 and R 4 is preferably 1 to 18, more preferably 4 to 12, and even more preferably 8.
- Examples of the compound represented by the formula (C1-3) include dialkyl phosphate (that is, a compound in which R 5 and R 6 are alkyl groups) and the like.
- Specific examples of the dialkyl phosphate include dibutyl phosphate and bis(2-ethylhexyl) phosphate.
- R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a carbon atom containing an alkyl group. It may be one or more of a hydrogen group, a hydrocarbon group containing an aromatic ring, and a hydrocarbon group containing an aliphatic ring. The hydrocarbon group may have a partially unsaturated group, and may have an arbitrary atom or substituent. At this time, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are preferably hydrocarbon groups containing an alkyl group. Further, the hydrocarbon group is preferably an unsubstituted saturated group. R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are preferably the same.
- Examples of the (C2) phosphite include trimethylphosphite, triethylphosphite, tri-n-butylphosphite, tris(2-ethylhexyl)phosphite, triisooctylphosphite, tridecylphosphite, triisodecylphosphite.
- the (C2) phosphite is a compound represented by the formula (C2-1), a compound represented by the formula (C2-2), a compound represented by the formula (C2-3), or a compound represented by the formula (C2-4). ), a compound represented by formula (C2-5), and a compound represented by formula (C2-6).
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are each independent. Shows a hydrocarbon group which may have a substituent.
- Examples of the substituent that the hydrocarbon group in R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 may have: An oxyalkyl group and the like can be mentioned.
- the hydrocarbon group in R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 is preferably an unsubstituted hydrocarbon group.
- the hydrocarbon group in R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 is preferably an alkyl group or an aryl group.
- a group or a phenyl group is more preferable, and an alkyl group is still more preferable.
- the number of carbon atoms in the alkyl group may be, for example, 1 to 30, preferably 1 to 18.
- R 8 and R 9 in formula (C2-2), R 10 , R 11 and R 12 in formula (C2-3), R 13 and R 14 in formula (C2-4), and formula (C2 R 15 and R 16 in -5) are preferably the same as each other in each formula.
- Examples of the compound represented by the formula (C2-1) include monoalkyl phosphite (that is, a compound in which R 7 is an alkyl group).
- Examples of the compound represented by the formula (C2-2) include dialkyl phosphites (that is, compounds in which R 8 and R 9 are alkyl groups).
- Examples of the compound represented by the formula (C2-3) include trialkyl phosphites (that is, compounds in which R 10 , R 11 and R 12 are alkyl groups) and the like. Further, specific examples of the compound represented by the formula (C2-3) include triethylphosphite, tris(2-ethylhexyl)phosphite, tridecylphosphite, trilaurylphosphite, tris(tridecyl)phosphite, trio. Examples thereof include rail phosphite and diphenyl monodecyl phosphite.
- Examples of the compound represented by the formula (C2-4) include bis(alkyl)pentaerythritol diphosphite (that is, a compound in which R 13 and R 14 are alkyl groups) and the like.
- specific examples of the compound represented by the formula (C2-4) include bis(decyl)pentaerythritol diphosphite, bis(tridecyl)pentaerythritol diphosphite, and distearyl pentaerythritol diphosphite. ..
- Examples of the compound represented by the formula (C2-5) include dialkyl hydrogen phosphite (that is, a compound in which R 15 and R 16 are alkyl groups) and the like. Further, specific examples of the compound represented by the formula (C2-5) include diethyl hydrogen phosphite, bis(2-ethylhexyl) hydrogen phosphite, dilauryl hydrogen phosphite, dioleyl hydrogen phosphite, and the like.
- Examples of the compound represented by the formula (C2-6) include monoalkyl hydrogen phosphite (that is, a compound in which R 17 is an alkyl group) and the like.
- specific examples of the compound represented by the formula (C2-6) include monoethyl hydrogen phosphite, mono(2-ethylhexyl) hydrogen phosphite, monolauryl hydrogen phosphite, monooleyl hydrogen phosphite, and the like. ..
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are each Independently, it may be one or more of a hydrocarbon group containing an alkyl group, a hydrocarbon group containing an aromatic ring, and a hydrocarbon group containing an aliphatic ring.
- the hydrocarbon group may have a partially unsaturated group, and may have an arbitrary atom or substituent.
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are preferably hydrocarbon groups containing an alkyl group.
- hydrocarbon group is preferably an unsubstituted saturated group.
- R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are preferably the same.
- trimethylphosphite triethylphosphite, tri-n-butylphosphite, tris(2-ethylhexyl)phosphite, triisooctylphosphite, tridecylphosphite, triisodecylphosphite, trisphosphite.
- a compound represented by the compound represented by the formula (C2-3) such as (tridecyl)phosphite, trioleylphosphite, tristearylphosphite, triphenylphosphite, tris(nonylphenyl)phosphite, and diphenylmonodecylphosphite.
- Trialkyl phosphites such as triisodecyl phosphite, tris(tridecyl)phosphite, trioleyl phosphite and tristearyl phosphite are preferred.
- trialkyl phosphites tridecyl phosphite is preferred.
- the amount of the (C) phosphoric acid compound used is preferably 0.1 to 5 parts by mass, and more preferably 0.02 to 3 parts by mass, relative to 100 parts by mass of the (A) cationically polymerizable compound.
- the amount of the (C) phosphoric acid compound used is 0.1 parts by mass or more, the increase in viscosity after light irradiation can be suppressed, and when it is 5 parts by mass or less, the photocurability does not deteriorate.
- the composition of this embodiment may contain a photosensitizer.
- the photosensitizer is a compound that absorbs energy rays and efficiently generates cations from the photocationic polymerization initiator.
- the photosensitizer is not particularly limited, benzophenone derivative, phenothiazine derivative, phenyl ketone derivative, naphthalene derivative, anthracene derivative, phenanthrene derivative, naphthacene derivative, chrysene derivative, perylene derivative, pentacene derivative, acridine derivative, benzothiazole derivative, Benzoin derivative, fluorene derivative, naphthoquinone derivative, anthraquinone derivative, xanthene derivative, xanthone derivative, thioxanthene derivative, thioxanthone derivative, coumarin derivative, ketocoumarin derivative, cyanine derivative, azine derivative, thiazine derivative, oxazine derivative, indoline derivative, azulene derivative, tri Examples thereof include an allylmethane derivative, a phthalocyanine derivative, a spiropyran derivative, a spirooxazine derivative,
- phenylketone derivatives such as 2-hydroxy-2-methyl-1-phenyl-propan-1-one and/or anthracene derivatives such as 9,10-dibutoxyanthracene are preferable, and anthracene derivatives are more preferable.
- anthracene derivatives 9,10-dibutoxyanthracene is preferred.
- the amount of the photosensitizer used is preferably 0.01 to 10 parts by mass with respect to 100 parts by mass of the cationically polymerizable compound (A), since the photocurability does not deteriorate and the storage stability does not decrease. It is more preferably 0.02 to 5 parts by mass.
- the composition of the present embodiment may contain a silane coupling agent.
- a silane coupling agent By containing a silane coupling agent, the composition of the present embodiment exhibits excellent adhesiveness and adhesive durability.
- the silane coupling agent is not particularly limited, but ⁇ -chloropropyltrimethoxysilane, vinyltrimethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, vinyl-tris( ⁇ -methoxyethoxy)silane, ⁇ -(meth) Acryloxypropyltrimethoxysilane, ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, N- ⁇ -(aminoethyl)- ⁇ -aminopropyltrimethoxysilane, N- ⁇ -(aminoethyl)- ⁇ -aminopropylmethyldimethoxysilane
- silane coupling agents may be selected and used.
- ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -(meth)acryloxypropyltrimethoxysilane At least one selected from the group consisting of silanes is preferable, and ⁇ -glycidoxypropyltrimethoxysilane is more preferable.
- the amount of the silane coupling agent used is preferably 0.1 to 10 parts by mass, based on 100 parts by mass of the components (A) and (B), from the viewpoint of obtaining adhesiveness and adhesive durability. 0.2 to 5 parts by mass is more preferable.
- the light source used for curing or bonding the composition of the present embodiment is not particularly limited, but a halogen lamp, a metal halide lamp, a high power metal halide lamp (containing indium and the like), a low pressure mercury lamp, a high pressure mercury lamp, an ultra high pressure Examples thereof include a mercury lamp, a xenon lamp, a xenon excimer lamp, a xenon flash lamp, and a light emitting diode (hereinafter referred to as LED). These light sources are preferable because they can efficiently irradiate energy rays corresponding to the reaction wavelength of each photocationic polymerization initiator.
- the above light sources have different emission wavelengths and energy distributions. Therefore, the light source is appropriately selected depending on the reaction wavelength of the photocationic polymerization initiator. Further, natural light (sunlight) can also be a reaction initiation light source.
- direct irradiation or concentrated irradiation by a reflecting mirror or fiber may be performed.
- a low wavelength cut filter, a heat ray cut filter, a cold mirror, etc. can also be used.
- the composition of the present embodiment may be subjected to post heat treatment in order to accelerate the curing rate after light irradiation.
- the temperature of the post-heating is preferably 150° C. or lower, and more preferably 80° C. or lower in that it does not damage the organic electroluminescence element when used for sealing the organic electroluminescence element. Further, the post-heating temperature is preferably 60° C. or higher.
- composition of this embodiment may be used as an adhesive.
- the adhesive of the present embodiment can be suitably used for adhesion of packages such as organic electroluminescence elements.
- the method for producing the composition of the present embodiment is not particularly limited as long as the above components can be sufficiently mixed.
- the mixing method of each component is not particularly limited, and examples thereof include a stirring method using a stirring force accompanied by rotation of a propeller, a method using a normal disperser such as a planetary stirrer by rotation and revolution, and the like. These mixing methods are preferable in that low-cost and stable mixing can be performed.
- a step of applying the composition to the whole surface or a part of one base material, and an organic electroluminescence element of the base material to which the composition is applied for example, a step of applying the composition to the whole surface or a part of one base material, and an organic electroluminescence element of the base material to which the composition is applied.
- the composition of the present embodiment is applied on one substrate (back plate), and the composition is irradiated with light. And the like, and then the light is blocked, and the back plate and the substrate on which the electroluminescence element is formed are bonded together via the composition.
- the organic electroluminescence element can be sealed without exposing it to light or heat.
- the organic electroluminescence display device can also be manufactured by a method in which one substrate is coated with the composition of the present embodiment, the other substrate is bonded via the composition, and then the composition is irradiated with light.
- the composition of the present embodiment preferably has a viscosity of 10 minutes after the light irradiation is less than 5 times the viscosity before the light irradiation.
- UV is preferable.
- the viscosity 10 minutes after UV irradiation with a high pressure mercury lamp at 100 mW/cm 2 for 30 seconds is less than 5 times the viscosity before UV irradiation.
- the photocationic polymerization initiator (B) absorbs the irradiated light and is excited, and the excited species are decomposed to generate an acid.
- composition of the present embodiment has a small increase in viscosity after irradiation with light, can suppress the generation of outgas, and is unlikely to deteriorate the organic electroluminescence element.
- one aspect of the present invention may be a cured product obtained by curing the above composition.
- Another aspect of the present invention may be a sealing material for an organic electroluminescence element, which includes the above-mentioned cured body.
- the encapsulant may be a cured product, and may include a cured product of the composition and other constituent materials.
- Other constituent materials include, for example, a silicon nitride film, a silicon oxide film, an inorganic layer such as silicon nitride oxide, an inorganic filler such as silica, mica, kaolin, talc, and aluminum oxide.
- Yet another aspect of the present invention may be an organic electroluminescence display device including an organic electroluminescence element and the above-mentioned sealing material for organic electroluminescence element.
- the method for manufacturing an organic electroluminescence display device comprises a first member, an attaching step of attaching the above composition, an irradiation step of irradiating the attached composition with light, and a light irradiation. And a laminating step of laminating the first member and the second member via the above composition.
- the first member may be a substrate and the second member may be an organic electroluminescent element. The conditions and the like of each step in this manufacturing method may be appropriately selected based on the description of the above embodiment.
- (A-1) 3′,4′-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (“Celoxide 2021P” manufactured by Daicel Chemical Industries, Ltd.)
- (A-1-2) Hydrogenated bisphenol A type epoxy resin ("YX8000” manufactured by Mitsubishi Chemical Corporation, molecular weight 380 to 430)
- (A-1-3) 3,4-epoxycyclohexyl methyl methacrylate ("Cyclomer M100" manufactured by Daicel)
- A-2) The following were used as the aromatic compound having an epoxy group.
- A-2-1-1) Bisphenol A type epoxy resin ("jER828” manufactured by Mitsubishi Chemical Corporation, molecular weight 360 to 390)
- A-2-1-2) Bisphenol A type epoxy resin ("YL980” manufactured by Mitsui Chemicals, molecular weight 240)
- A-2-2-1) Bisphenol F-type epoxy resin (“jER806” manufactured by Mitsubishi Chemical Corporation, molecular weight 320 to 340)
- A-2-2-2) Bisphenol F type epoxy resin (“YL983U” manufactured by Mitsui Chemicals, Inc., molecular weight 360 to 380)
- A-2-2-3) Bisphenol F type epoxy resin ("KRM-2490” manufactured by ADEKA, molecular weight 340 to 380)
- B-1 Triarylsulfonium salt hexafluoroantimonate
- ADEKA PTOMER SP-170 Triarylsulfonium salt hexafluoroantimonate
- B-2 Triarylsulfonium salt (diphenyl 4-thiophenoxyphenylsulfonium tris(pentafluoroethyl)trifluorophosphate, "CPI-200K” manufactured by San-Apro Ltd., anionic species being phosphorus compound)
- C-1 Tris(2-ethylhexyl) phosphate (“TOP” manufactured by Daihachi Chemical Industry Co., Ltd.)
- C-2) Tridecyl phosphite ("JP-310" manufactured by Johoku Chemical Industry Co., Ltd.)
- C-3) Bis(decyl)pentaerythritol diphosphite ("JPE-10” manufactured by Johoku Chemical Co., Ltd.)
- C-4) Bis(2-ethylhexyl) hydrogen phosphite (“JPE-208” manufactured by Johoku Chemical Industry Co., Ltd.)
- C-5) Diphenyl monodecyl phosphite ("JPM-311” manufactured by Johoku Chemical Industry Co., Ltd.)
- C-6 Comparative Example Tri-n-octylphosphine oxide (“TOPO (registered trademark)” manufactured by Daihachi Chemical Industry Co., Ltd.)
- TOPO Tri-n-octy
- the viscosity (shear viscosity) of the sealant was measured using an E-type viscometer (1°34′ ⁇ R24 cone rotor) under the conditions of a temperature of 25° C. and a rotation speed of 10 rpm.
- the viscosity change rate is preferably 10 or less, more preferably 9 or less, most preferably 8 or less, still more preferably 6 or less, and even more preferably 5 or less, from the viewpoint of good slow curing property.
- the sealant was cured under the following light irradiation conditions. After photocuring the encapsulant with a UV curing device equipped with an electrodeless discharge metal halide lamp (manufactured by Fusion Co., Ltd.) under the condition of an integrated light quantity of 4,000 mJ/cm 2 at a wavelength of 365 nm, in an oven at 80° C., Post-heat treatment was carried out for 30 minutes to obtain a cured product.
- a UV curing device equipped with an electrodeless discharge metal halide lamp (manufactured by Fusion Co., Ltd.) under the condition of an integrated light quantity of 4,000 mJ/cm 2 at a wavelength of 365 nm, in an oven at 80° C.
- the sealant was applied on a glass substrate so that the amount applied per unit area was 10 mg/cm 2, and the substrate was irradiated with an ultraviolet ray irradiation device (manufactured by HOYA, ultra-high pressure mercury lamp irradiation device “UL-750”). Was used to irradiate ultraviolet rays having a wavelength of 365 nm and 100 mW/cm 2 for 10 seconds. Thereafter, the mixture was heated at 80° C. for 60 minutes, the generated gas component was collected and concentrated, and the amount of outgas was measured by GC/MS (manufactured by Agilent Technology, “GC/MS 7890B/5977B”). The amount of outgas is preferably 60 ppm or less.
- anode film thickness 250nm ⁇ Hole injection layer Copper phthalocyanine Thickness 30nm -Hole transport layer N,N'-diphenyl-N,N'-dinaphthylbenzidine ( ⁇ -NPD) thickness 20 nm -Light emitting layer Tris(8-hydroxyquinolinato) aluminum (metal complex material), thickness of light emitting layer 1000 ⁇ ⁇ Electron injection layer Lithium fluoride Thickness 1nm ⁇ Cathode aluminum, anode film thickness 250nm
- the diameter of the dark spot is preferably 300 ⁇ m or less, more preferably 150 ⁇ m or less, most preferably 100 ⁇ m or less, further preferably 50 ⁇ m or less, and even more preferably no dark spot.
- composition of the present embodiment does not easily generate outgas when irradiated with light, and thus has good durability and does not deteriorate the element. From this result, it was confirmed that the composition of the present embodiment is suitable as a sealant for an organic electroluminescence element.
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| KR1020217022856A KR20210132001A (ko) | 2019-02-21 | 2020-02-20 | 조성물 |
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| JP2023022040A (ja) * | 2019-02-21 | 2023-02-14 | デンカ株式会社 | 組成物 |
| WO2023147993A1 (de) | 2022-02-04 | 2023-08-10 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Kationisch polymerisierbare flammgeschützte massen |
| WO2024095948A1 (ja) * | 2022-11-04 | 2024-05-10 | デンカ株式会社 | 封止剤、硬化体、表示装置、表示装置の製造方法、太陽電池および組成物 |
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| KR20210061392A (ko) * | 2018-09-26 | 2021-05-27 | 덴카 주식회사 | 유기 일렉트로루미네센스 표시 소자용 봉지제 |
| KR20230048965A (ko) | 2021-10-05 | 2023-04-12 | 주식회사 엘지에너지솔루션 | 이차전지 트레이 |
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| JP7397151B2 (ja) | 2019-02-21 | 2023-12-12 | デンカ株式会社 | 組成物 |
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| Publication number | Publication date |
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| CN113272383A (zh) | 2021-08-17 |
| JP2023022040A (ja) | 2023-02-14 |
| JP7397151B2 (ja) | 2023-12-12 |
| CN113272383B (zh) | 2023-11-17 |
| TWI822961B (zh) | 2023-11-21 |
| KR20210132001A (ko) | 2021-11-03 |
| TW202045613A (zh) | 2020-12-16 |
| JP7220277B2 (ja) | 2023-02-09 |
| JPWO2020171186A1 (ja) | 2021-12-23 |
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