CN112753280A - Ultraviolet-curable resin composition, method for producing organic EL light-emitting device, and organic EL light-emitting device - Google Patents
Ultraviolet-curable resin composition, method for producing organic EL light-emitting device, and organic EL light-emitting device Download PDFInfo
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- CN112753280A CN112753280A CN201980063298.1A CN201980063298A CN112753280A CN 112753280 A CN112753280 A CN 112753280A CN 201980063298 A CN201980063298 A CN 201980063298A CN 112753280 A CN112753280 A CN 112753280A
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- compound
- organic
- acrylic compound
- ultraviolet
- composition
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- 239000011342 resin composition Substances 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- -1 acrylic compound Chemical class 0.000 claims abstract description 225
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 239000003566 sealing material Substances 0.000 claims abstract description 77
- 238000009835 boiling Methods 0.000 claims abstract description 45
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 239000003999 initiator Substances 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 238000007789 sealing Methods 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 34
- 230000009477 glass transition Effects 0.000 claims description 33
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 8
- 239000000126 substance Substances 0.000 abstract description 22
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 122
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 82
- 239000000758 substrate Substances 0.000 description 43
- 125000000217 alkyl group Chemical group 0.000 description 36
- 238000002161 passivation Methods 0.000 description 27
- 238000000576 coating method Methods 0.000 description 25
- 239000011248 coating agent Substances 0.000 description 24
- 230000002745 absorbent Effects 0.000 description 16
- 239000002250 absorbent Substances 0.000 description 16
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 15
- 239000002270 dispersing agent Substances 0.000 description 15
- 229910052581 Si3N4 Inorganic materials 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 14
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
- 229910010272 inorganic material Inorganic materials 0.000 description 9
- 239000011147 inorganic material Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
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- 125000000524 functional group Chemical group 0.000 description 6
- 238000010943 off-gassing Methods 0.000 description 6
- 238000005192 partition Methods 0.000 description 6
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 5
- 150000004292 cyclic ethers Chemical group 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000002347 octyl 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])[H] 0.000 description 4
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- MJYFYGVCLHNRKB-UHFFFAOYSA-N 1,1,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)CF MJYFYGVCLHNRKB-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
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- HMIBQFXWSUBFTG-UHFFFAOYSA-N 1-[4-(diethylamino)phenyl]ethanone Chemical compound CCN(CC)C1=CC=C(C(C)=O)C=C1 HMIBQFXWSUBFTG-UHFFFAOYSA-N 0.000 description 1
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- LRZPQLZONWIQOJ-UHFFFAOYSA-N 10-(2-methylprop-2-enoyloxy)decyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOC(=O)C(C)=C LRZPQLZONWIQOJ-UHFFFAOYSA-N 0.000 description 1
- RHNJVKIVSXGYBD-UHFFFAOYSA-N 10-prop-2-enoyloxydecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCOC(=O)C=C RHNJVKIVSXGYBD-UHFFFAOYSA-N 0.000 description 1
- HYQASEVIBPSPMK-UHFFFAOYSA-N 12-(2-methylprop-2-enoyloxy)dodecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCCOC(=O)C(C)=C HYQASEVIBPSPMK-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
- WKIFJRSHLQGWQF-UHFFFAOYSA-N 2-(oxiran-2-yl)pentyl 2-methylprop-2-enoate Chemical compound CCCC(COC(C(C)=C)=O)C1OC1 WKIFJRSHLQGWQF-UHFFFAOYSA-N 0.000 description 1
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 1
- LJRSZGKUUZPHEB-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COC(C)COC(=O)C=C LJRSZGKUUZPHEB-UHFFFAOYSA-N 0.000 description 1
- OWDBMKZHFCSOOL-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)propoxy]propoxy]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(C)COC(C)COC(=O)C(C)=C OWDBMKZHFCSOOL-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
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- PAAVDLDRAZEFGW-UHFFFAOYSA-N 2-butoxyethyl 4-(dimethylamino)benzoate Chemical compound CCCCOCCOC(=O)C1=CC=C(N(C)C)C=C1 PAAVDLDRAZEFGW-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 1
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 1
- UVRCNEIYXSRHNT-UHFFFAOYSA-N 3-ethylpent-2-enamide Chemical compound CCC(CC)=CC(N)=O UVRCNEIYXSRHNT-UHFFFAOYSA-N 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
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- ZWAPMFBHEQZLGK-UHFFFAOYSA-N 5-(dimethylamino)-2-methylidenepentanamide Chemical compound CN(C)CCCC(=C)C(N)=O ZWAPMFBHEQZLGK-UHFFFAOYSA-N 0.000 description 1
- FDWQGNULGGFFDP-UHFFFAOYSA-N 5-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C=CC1CCCC2OC12 FDWQGNULGGFFDP-UHFFFAOYSA-N 0.000 description 1
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- CAKHDJPNOKXIED-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-5-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCCC2OC12 CAKHDJPNOKXIED-UHFFFAOYSA-N 0.000 description 1
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- 150000004056 anthraquinones Chemical class 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
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- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/841—Self-supporting sealing arrangements
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Electroluminescent Light Sources (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The invention provides an ultraviolet-curable resin composition which can be used for preparing a sealing material for sealing an organic EL element and can prevent moisture from entering the organic EL element. The ultraviolet-curable resin composition contains an acrylic compound (A) and a photopolymerization initiator (B). Acrylic acid compoundThe substance (A) contains a compound having the formula CH2＝CR1‑COO‑(R3‑O)n‑CO‑CR2＝CH2An acrylic compound (A1) having the structure shown above and having a boiling point of 270 ℃ or higher. R1And R2Each is hydrogen or methyl, n is an integer of 1 or more, R3Is an alkylene group having 3 or more carbon atoms. The percentage of the acrylic compound (a1) to the acrylic compound (a) is 50% by mass or more. The acrylic compound (A) does not contain a compound having a boiling point of 260 ℃ or lower, or the proportion of a compound having a boiling point of 260 ℃ or lower in the acrylic compound (A) is 10% by mass or lower.
Description
Technical Field
The present invention relates to an ultraviolet-curable resin composition, a method for manufacturing an organic EL light-emitting device, and more particularly, to an ultraviolet-curable resin composition for sealing an organic EL element, a method for manufacturing an organic EL light-emitting device using the ultraviolet-curable resin composition, and an organic EL light-emitting device provided with the sealing material.
Background
Organic EL light-emitting devices are used for illumination, display, and the like, and are expected to be widely used in the future.
Among organic EL light-emitting devices, a device called a top emission type is configured, for example, by disposing an organic EL element on a support substrate, disposing a transparent substrate so as to face the support substrate, and filling a transparent sealing material between the support substrate and the transparent substrate. In this case, light emitted from the organic EL element can be emitted to the outside through the sealing material and the transparent substrate.
The sealing material suppresses the generation and growth of dark spots (dark spots) in the organic EL element by suppressing the intrusion of moisture into the organic EL element. The dark spot is a portion of the organic EL element that does not emit light due to moisture degradation.
The sealing material is made of a material containing an organic resin selected from an epoxy resin and an acrylic resin, for example (see patent document 1). In particular, when an acrylic resin is used, the material can be cured by ultraviolet irradiation or the like to form a sealing material, and therefore, the sealing material can be formed without applying a load due to heat to the organic EL element.
Even when the organic EL element is covered with the sealing material, the penetration of moisture into the organic EL element may not be sufficiently suppressed.
Documents of the prior art
Patent document
Patent document 1: japanese patent No. 5581332
Disclosure of Invention
The present invention addresses the problem of providing an ultraviolet-curable resin composition that can be used for producing a sealing material for sealing an organic EL element and that can prevent moisture from entering the organic EL element, a method for producing an organic EL light-emitting device using the ultraviolet-curable resin composition, and an organic EL light-emitting device provided with a sealing material that includes a cured product of the ultraviolet-curable resin composition.
An ultraviolet-curable resin composition according to one embodiment of the present invention is used for sealing an organic EL, and includes an acrylic compound (a) and a photopolymerization initiator (B), wherein the acrylic compound (a) includes an acrylic compound (a1) having a structure represented by formula (1) below and a boiling point of 270 ℃ or higher.
CH2＝CR1-COO-(R3-O)n-CO-CR2＝CH2…(1)
In the formula (1), R1And R2Each is hydrogen or methyl, n is an integer of 1 or more, R3Is an alkylene group having 3 or more carbon atoms, and when n is 2 or more, a plurality of R's in one molecule3May be the same or different. The percentage of the acrylic compound (a1) to the acrylic compound (a) is 50% by mass or more. The acrylic compound (A) does not contain a compound having a boiling point of 260 ℃ or lower, or the proportion of a compound having a boiling point of 260 ℃ or lower in the acrylic compound (A) is 10% by mass or lower.
A method for manufacturing an organic EL light-emitting device according to an aspect of the present invention is a method for manufacturing an organic EL light-emitting device including an organic EL element and a sealing material covering the organic EL element, the method including: the sealing material is produced by molding the ultraviolet-curable resin composition by an ink jet method, and then curing the ultraviolet-curable resin composition by irradiation with ultraviolet light.
An organic EL light-emitting device according to an embodiment of the present invention includes an organic EL element and a sealing material covering the organic EL element, and the sealing material is a cured product of the ultraviolet-curable resin composition.
Drawings
Fig. 1 is a schematic cross-sectional view showing a first example of an organic EL light-emitting device according to an embodiment of the present invention.
Fig. 2 is a schematic cross-sectional view showing a second example of the organic EL light-emitting device according to the embodiment of the present invention.
Detailed Description
Hereinafter, one embodiment of the present invention will be described.
The ultraviolet-curable resin composition for sealing an organic EL element (hereinafter also referred to as composition (X)) of the present embodiment contains an acrylic compound (a) and a photopolymerization initiator (B). The acrylic compound (A) contains an acrylic compound (A1) having a structure represented by the following formula (1) and a boiling point of 270 ℃ or higher.
CH2＝CR1-COO-(R3-O)n-CO-CR2＝CH2…(1)
In the formula (1), R1And R2Each is hydrogen or methyl, n is an integer of 1 or more, R3Is an alkylene group having 3 or more carbon atoms, and when n is 2 or more, a plurality of R's in one molecule3May be the same or different.
The percentage of the acrylic compound (a1) to the acrylic compound (a) is 50% by mass or more. The acrylic compound (A) does not contain a compound having a boiling point of 260 ℃ or lower, or the proportion of a compound having a boiling point of 260 ℃ or lower in the acrylic compound (A) is 10% by mass or lower.
The sealing material 5 (see fig. 1) of the organic EL light-emitting device 1 can be prepared from the composition (X). The outgas due to the acrylic compound (a1) is less likely to occur from the sealing material 5. Therefore, voids due to outgassing can be less likely to be generated in the organic EL light-emitting device 1. Therefore, moisture is less likely to enter the organic EL element through the gap. Further, the acrylic compound (a1) is less likely to increase the affinity of the sealing material 5 for water, and therefore, moisture is less likely to enter the organic EL element through the sealing material 5. Therefore, moisture is less likely to enter the organic EL element.
The glass transition temperature of the cured product of the composition (X) is preferably 80 ℃ or higher. That is, the composition (X) preferably has a property of being cured into a cured product having a glass transition temperature of 80 ℃ or higher. In this case, the cured product can have good heat resistance. Therefore, for example, when a treatment accompanied by a temperature increase is performed on a cured product, the cured product is less likely to deteriorate. Therefore, for example, when the passivation layer 6 is formed by laminating the passivation layer on the sealing material 5 formed of the composition (X) by a vapor deposition method such as a plasma CVD method, the sealing material 5 is less likely to be deteriorated even if the sealing material 5 is heated. The glass transition temperature of the cured product is more preferably 90 ℃ or higher, and still more preferably 100 ℃ or higher. The glass transition temperature of the cured product can be achieved by the composition of the composition (X) described in detail below.
The viscosity of the composition (X) at 25 ℃ is preferably 1 mPas to 30 mPas. In this case, the composition (X) can be easily molded at ordinary temperature by a method such as a casting method, or can be molded by an ink-jet method. The viscosity is more preferably 25 mPas or less, still more preferably 20 mPas or less, and particularly preferably 15 mPas or less. The viscosity is also preferably 5 mPas or more.
The viscosity of the composition (X) at 40 ℃ is preferably 1 mPas or more and 30 mPas or less. In this case, the viscosity of the composition (X) can be reduced by slightly heating the composition (X) regardless of the viscosity at room temperature. Therefore, if heating is performed, the composition (X) can be easily molded by a method such as a casting method, or can be molded by an ink-jet method. Further, since the viscosity of the composition (X) can be reduced without substantially heating the composition (X), the composition of the composition (X) is less likely to change due to volatilization of components in the composition (X). The viscosity is more preferably 25 mPas or less, still more preferably 20 mPas or less, and particularly preferably 15 mPas or less. The viscosity is also preferably 5 mPas or more.
The viscosity of the composition (X) was measured at a shear rate of 100s-1 using a rheometer. As the rheometer, for example, model DHR-2 manufactured by Anton Paar Japan can be used.
The low viscosity at 25 ℃ or 40 ℃ of such a composition (X) can be achieved by the composition of the composition (X) as specified hereinafter.
The total light transmittance of the cured product of the composition (X) is preferably 90% or more when the thickness dimension is 10 μm. In this case, if the cured product is applied to the sealing material 5 in the organic EL light-emitting device 1, the efficiency of extracting light that is transmitted through the sealing material 5 and emitted to the outside can be particularly improved. The light transmittance of such a cured product can also be achieved by the composition of the composition (X) described in detail below.
Hereinafter, the present embodiment will be described in more detail.
1. Structure of organic EL light emitting device
First, the structure of the organic EL light-emitting device 1 will be described. The organic EL light-emitting device 1 includes an organic EL element 4 and a sealing material 5 covering the organic EL element 4. The sealing material 5 may cover the organic EL element 4 in a state of being in direct contact with the organic EL element 4, or may cover the organic EL element 4 with some layers interposed between the sealing material 5 and the organic EL element 4. Note that EL is an abbreviation for electroluminescence. In addition, the organic EL element 4 is also referred to as an organic light emitting diode.
A first example of the structure of the organic EL light-emitting device 1 is described with reference to fig. 1. The organic EL light-emitting device 1 is of a top emission type. The organic EL light-emitting device 1 includes a support substrate 2, a transparent substrate 3 facing the support substrate 2 with a space therebetween, an organic EL element 4 located on a surface of the support substrate 2 facing the transparent substrate 3, and a sealing material 5 filled between the support substrate 2 and the transparent substrate 3. In the first example, the organic EL light-emitting device 1 includes the passivation layer 6 covering the surface of the support substrate 2 facing the transparent substrate 3 and the organic EL element 4. That is, the passivation layer 6 is interposed between the organic EL element 4 and the sealing material 5 covering the organic EL element 4.
The support substrate 2 is made of, for example, a resin material, but is not limited thereto. The transparent substrate 3 is made of a material having translucency. The transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate. The organic EL element 4 includes, for example, a pair of electrodes and an organic light-emitting layer located between the electrodes. The organic light-emitting layer includes, for example, a hole injection layer, a hole transport layer, an organic light-emitting layer, and an electron transport layer, and these layers are stacked in this order. Although only one organic EL element 4 is shown in fig. 1, the organic EL light-emitting device 1 may include a plurality of organic EL elements 4, and the plurality of organic EL elements 4 may be arrayed on the support substrate 2. The passivation layer 6 is preferably made of silicon nitride or silicon oxide.
A second example of the structure of the organic EL light-emitting device 1 is described with reference to fig. 2. The same reference numerals as in fig. 1 are given to elements common to the first example shown in fig. 1, and detailed description thereof is omitted as appropriate. The organic EL light-emitting device 1 shown in fig. 2 is also of a top emission type. The organic EL light-emitting device 1 includes a support substrate 2, a transparent substrate 3 facing the support substrate 2 with a space therebetween, an organic EL element 4 located on a surface of the support substrate 2 facing the transparent substrate 3, and a sealing material 5 covering the organic EL element 4.
The organic EL element 4 includes, for example, a pair of electrodes 41 and 43 and an organic light-emitting layer 42 located between the electrodes 41 and 43, as in the case of the first example. The organic light-emitting layer 42 includes, for example, a hole injection layer 421, a hole transport layer 422, an organic light-emitting layer 423, and an electron transport layer 424, and these layers are stacked in this order.
The organic EL light-emitting device 1 includes a plurality of organic EL elements 4, and the plurality of organic EL elements 4 form an array 9 (hereinafter referred to as an element array 9) on the support substrate 2. The element array 9 further includes partition walls 7. The partition walls 7 are provided on the support substrate 2 to partition the adjacent two organic EL elements 4. The partition walls 7 are formed by molding a photosensitive resin material by photolithography, for example. The element array 9 further includes a connection wiring 8 for electrically connecting the electrode 43 of the adjacent organic EL element 4 and the electron transport layer 424 to each other. The connection wiring 8 is provided on the partition wall 7.
The organic EL light-emitting device 1 further includes a passivation layer 6 covering the organic EL element 4. The passivation layer 6 is preferably made of silicon nitride or silicon oxide. The passivation layer 6 includes a first passivation layer 61 and a second passivation layer 62. The first passivation layer 61 covers the element array 9 in a state of being in direct contact with the element array 9, thereby covering the organic EL elements 4. The second passivation layer 62 is disposed at a position opposite to the element array 9 with respect to the first passivation layer 61, and a space is provided between the second passivation layer 62 and the first passivation layer 61. The sealing material 5 is filled between the first passivation layer 61 and the second passivation layer 62. That is, the first passivation layer 61 is interposed between the organic EL element 4 and the sealing material 5 covering the organic EL element 4.
Further, the second sealing material 52 is filled between the second passivation layer 62 and the transparent substrate 3. The second sealing member 52 is made of, for example, a transparent resin material. The material of the second sealing material 52 is not particularly limited. The material of the second sealing member 52 may be the same as or different from that of the sealing member 5.
The sealing material 5 in the organic EL light-emitting device 1 having the above-described exemplary structure can be produced from the ultraviolet-curable resin composition of the present embodiment. That is, the ultraviolet curable resin composition is used to produce the sealing material 5 for the organic EL element 4. In other words, the ultraviolet-curable resin composition is preferably a composition for producing a sealing material, a composition for sealing an organic EL element, or a composition for producing an organic EL light-emitting device.
2. Ultraviolet-curable resin composition
The ultraviolet-curable resin composition (hereinafter, also referred to as composition (X)) of the present embodiment will be described.
As described above, the composition (X) contains the acrylic compound (a) and the photopolymerization initiator (B). When the composition (X) is irradiated with ultraviolet light, the photopolymerization initiator (B) initiates a photo radical polymerization reaction to cure the acrylic compound (a), whereby a cured product can be produced. The ingredients of composition (X) will be explained in more detail hereinafter.
As described above, the composition (X) contains the acrylic compound (a). The acrylic compound (a) has one or more (meth) acryloyl groups in one molecule. In addition, "(meth) acrylic acid" means at least one of "acrylic acid" and "methacrylic acid".
The viscosity at 25 ℃ of the whole of the acrylic compound (A) is preferably 50 mPas or less. In this case, the acrylic compound (a) can make the composition (X) particularly low in viscosity. The viscosity of the entire acrylic compound (a) is more preferably 30mPa · s or less, still more preferably 25mPa · s or less, and particularly preferably 20mPa · s or less. The viscosity of the entire acrylic compound (a) is, for example, 3mPa · s or more.
The viscosity of the whole acrylic compound (A) at 40 ℃ is preferably 50 mPas or less. In this case, the acrylic compound (a) can particularly reduce the viscosity of the composition (X) when heated. The viscosity of the whole of the acrylic compound (a) is more preferably 30mPa · s or less, still more preferably 25mPa · s or less, and particularly preferably 20mPa · s or less. The viscosity of the entire acrylic compound (a) is, for example, 3mPa · s or more.
The compounds that the acrylic compound (A) may contain are explained.
As described above, the acrylic compound (a) contains the acrylic compound (a1) having a structure represented by formula (1) and a boiling point of 270 ℃ or higher. In other words, the acrylic compound (a) contains the acrylic compound (a1), and the acrylic compound (a1) is composed of only at least one compound having a boiling point of 270 ℃ or higher among compounds having a structure represented by formula (1).
Since the boiling point of the acrylic compound (a1) is 270 ℃ or higher, the acrylic compound (a1) is less likely to volatilize from the composition (X) during storage of the composition (X) and when the composition (X) is heated. Therefore, the storage stability of the composition (X) is not easily impaired. Even if the acrylic compound (a1) remains unreacted in the cured product of the composition (X) and in the sealing material 5, outgassing from the cured product and the sealing material 5 due to the acrylic compound (a1) is less likely to occur. Therefore, voids due to outgassing are less likely to be generated in the organic EL light-emitting device 1. If there are voids in the organic EL light-emitting device 1, moisture may reach the organic EL element 4 through the voids, but if voids are not easily generated, moisture does not easily reach the organic EL element 4, and thus the organic EL element 4 is not easily deteriorated by moisture. The boiling point is a boiling point at normal pressure obtained by converting a boiling point under reduced pressure, and is obtained, for example, by a method shown in Science of Petroleum, vol.ii.p.1281 (1938). The boiling point of the acrylic compound (a1) is more preferably 280 ℃.
Further, the acrylic compound (A1) has a structure represented by the formula (1), particularly R of the formula (1)3The acrylic compound (a1) has a carbon number of 3 or more, and thus the affinity of the sealing material 5 for water is not easily improved. Therefore, moisture is less likely to enter the organic EL element through the sealing material 5. R3The number of carbon atoms of (2) is, for example, 3 to 15. Further, the acrylic compound (a1) having the structure represented by formula (1) and particularly having two (meth) acryloyl groups in one molecule can increase the glass transition temperature of the cured product, and therefore, the heat resistance of the cured product and the sealing material 5 can be improved. In addition, n in formula (1) is, for example, an integer of 1 to 12.
The percentage of the acrylic compound (a1) to the acrylic compound (a) is 50% by mass or more. Therefore, the storage stability of the composition (X) can be effectively improved, the outgas generated from the sealing material 5 can be effectively reduced, and the affinity of the sealing material 5 for water is particularly not easily improved. The percentage of the acrylic compound (a1) to the acrylic compound (a) is, for example, 100 mass% or less, or 95 mass% or less, preferably 80 mass% or less.
The viscosity of the acrylic compound (A1) at 25 ℃ is preferably 25 mPas or less. In this case, the acrylic compound (a1) can reduce the viscosity of the composition (X). The viscosity of the acrylic compound (A1) at 25 ℃ is more preferably 25 mPas or less, still more preferably 20 mPas or less, and particularly preferably 15 mPas or less. The viscosity of the acrylic compound (a1) at 25 ℃ is, for example, 1mPa · s or more, preferably 3mPa · s or more, and more preferably 5mPa · s or more.
The acrylic compound (a1) contains, for example, at least one compound selected from the group consisting of a di (meth) acrylate of an alkylene glycol, a di (meth) acrylate of a polyalkylene glycol, and a di (meth) acrylate of an alkylene oxide-modified alkylene glycol.
The di (meth) acrylate of an alkylene glycol is a compound in which n is 1 in the formula (1). In this case, R in the formula (1)3The number of carbon atoms of (C) is preferably 4 to 12. R3The polymer may be linear or branched. In particular, the di (meth) acrylate of the alkylene glycol preferably contains at least one compound selected from the group consisting of 1, 4-butanediol diacrylate, 1, 3-butanediol diacrylate, neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate, 1, 9-nonanediol diacrylate, 1, 10-decanediol diacrylate, 1, 4-butanediol dimethacrylate, 1, 3-butanediol dimethacrylate, neopentyl glycol dimethacrylate, 1, 6-hexanediol dimethacrylate, 1, 9-nonanediol dimethacrylate, 1, 10-decanediol dimethacrylate and 1, 12-dodecanediol dimethacrylate. The di (meth) acrylate of the alkylene glycol preferably contains a monomer selected from the group consisting of SR213, SR 195, SR212, SR247, SR238, 9-A, Sartomer, V230, HDDA, 1, 6HX-A, V260, 1, 9-ND-A, CD595, S595, and CD595at least one compound selected from among product No. SR214NS manufactured by artomer, product No. BD manufactured by new Zhongmura chemical industry, product No. SR297 manufactured by Sartomer, product No. SR248 manufactured by Sartomer, product No. LIGHT ESTER NP manufactured by Co-Roche chemical industry, product No. SR239NS manufactured by Sartomer, product No. LIGHT ESTER 1, 6HX manufactured by Co-Roche chemical industry, product No. HD-N manufactured by New Zhongmura chemical industry, product No. LIGHT ESTER 1, 9ND manufactured by Co-Roche chemical industry, product No. NOD-N manufactured by New Zhongmura chemical industry, product No. LIGHT ESTER 1, 10DC manufactured by Co-Roche chemical industry, product No. DOD-N manufactured by New Zhongmura chemical industry, and product No. SR262 manufactured by Sartomer.
The di (meth) acrylate of a polyalkylene glycol is a compound of formula (1) wherein n is 2 or more. n is, for example, 2 to 10, preferably 2 to 7, more preferably 2 to 6, and still more preferably 2 to 3. R3The number of carbon atoms of (B) is, for example, 2 to 5. The larger the number of carbon atoms, the higher the hydrophobicity of the cured product and the sealing material 5, and the less likely the moisture penetrates through the sealing material 5. The polyalkylene glycol di (meth) acrylate particularly preferably contains at least one compound selected from the group consisting of diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, hexaethylene glycol dimethacrylate, dipropylene glycol diacrylate, tripropylene glycol dimethacrylate and tetramethylene glycol diacrylate. The polyalkylene glycol di (meth) acrylate particularly preferably contains a compound selected from the group consisting of SR230, SR508NS, DPGDA, SR306NS, TPGDA, V310HP, APG200, SR205NS, LIGHT ACRYLATE PTMGA-250, SR231NS, LIGHT ESTER 2EG, SR205NS, LIGHT ESTER 3EG, and Sartomer LIGHT ESTERAt least one compound selected from the group consisting of Sedi product No. SR210NS, Kyoho chemical industries product No. LIGHT ESTER 4EG, Mitsubishi chemical industries product No. ACRYESTER HX, and Xinzhongmura chemical industries product No. 3 PG.
The di (meth) acrylate of the alkylene oxide-modified alkylene glycol contains, for example, propylene oxide-modified neopentyl glycol. The di (meth) acrylate of the alkylene oxide-modified alkylene glycol contains, for example, EBECRYL145, product number manufactured by Daicel corporation.
The percentage of the component having a boiling point of 270 ℃ or higher in the acrylic compound (A) is preferably 80% by mass or higher. When the acrylic compound (a) further contains a compound other than the acrylic compound (a1), the percentage of a component having a boiling point of 270 ℃ or higher among all components including the acrylic compound (a) and the compound other than the acrylic compound (a1) in the acrylic compound (a) is preferably 80% by mass or higher. In this case, the storage stability of the composition (X) is particularly less likely to be impaired, and outgassing from the cured product and the sealing material 5 is particularly less likely to occur. The percentage of the component having a boiling point of 280 ℃ or higher in the acrylic compound (a) is more preferably 80% by mass or higher.
Compounds other than the acrylic compound (a1) which the acrylic compound (a) may contain will be described.
The acrylic compound (a) may further contain a polyfunctional acrylic compound (a2) in addition to the acrylic compound (a 1). The polyfunctional acrylic compound (a2) can increase the glass transition temperature of the cured product, and therefore can improve the heat resistance of the cured product and the sealing material 5. The polyfunctional acrylic compound (a2) contains, for example, polyethylene glycol di (meth) acrylate.
The polyfunctional acrylic compound (a2) is preferably a compound (a21) having three or more (meth) acryloyl groups in one molecule. That is, the acrylic compound (a) preferably contains the compound (a 21). In this case, the compound (a21) may contain, for example, at least one selected from trimethylolpropane triacrylate and trimethylolpropane trimethacrylate. When the acrylic compound (a) contains the compound (a21), the compound (a21) can particularly increase the glass transition temperature of the cured product, and therefore can particularly improve the heat resistance of the cured product and the sealing material 5.
In the case where the acrylic compound (a) contains the compound (a21), the percentage of the compound (a21) to the acrylic compound (a) is preferably more than 0 mass% and 25 mass% or less. The percentage of the component (a3) is more preferably 10 mass% or more. In this case, the glass transition temperature of the cured product can be particularly increased. In addition, if the compound (a21) is 25% by mass or less, the viscosity of the composition (X) is less likely to increase due to the compound (a 21). If the percentage of the compound (a21) is 20% by mass or less, the viscosity of the composition (X) is particularly less likely to increase.
The acrylic compound (a) may further contain a monofunctional acrylic compound (a3) having only one (meth) acryloyl group in one molecule. The monofunctional acrylic compound (a3) can suppress shrinkage of the composition (X) upon curing. In addition, the monofunctional acrylic compound (a3) can contribute to lowering the viscosity of the composition (X). When the acrylic compound (a) contains the monofunctional acrylic compound (A3), the percentage of the monofunctional acrylic compound (A3) to the total amount of the acrylic compound (a) is preferably more than 0 mass% and 70 mass% or less. If the percentage of the monofunctional acrylic compound (A3) is more than 0% by mass, shrinkage of the composition (X) upon curing can be suppressed by the monofunctional acrylic compound (A3). The percentage of the monofunctional acrylic compound (a3) is more preferably 5% by mass or more. If the percentage of the monofunctional acrylic compound (A3) is 70% by mass or less, outgassing from the composition (X) and the cured product due to the monofunctional acrylic compound (A3) is less likely to occur. Further, if the amount of the monofunctional acrylic compound (a3) is 70% by mass or less, the amount of the polyfunctional component in the acrylic compound (a) can be ensured, and therefore, the heat resistance of the cured product and the sealing material 5 can be particularly improved by the polyfunctional component. The percentage of the monofunctional acrylic compound (A3) is more preferably 50% by mass or less, and the percentage of the monofunctional acrylic compound (A3) is more preferably 40% by mass or less, and particularly preferably 30% by mass or less.
The monofunctional acrylic compound (A3) contains, for example, a monomer selected from the group consisting of isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, 3, 5-trimethylcyclohexyl (meth) acrylate, 4-t-butylcyclohexyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxytriethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxyethyl (meth) acrylate, and mixtures thereof, Butoxyethyl (meth) acrylate, ethoxydiglycol (meth) acrylate, methoxydihexylethyl (meth) acrylate, ethyldiglycol (meth) acrylate, cyclic trimethylolpropane formal mono (meth) acrylate, imide (meth) acrylate, isoamyl (meth) acrylate, ethoxylated succinic (meth) acrylate, trifluoroethyl (meth) acrylate, omega-carboxy polycaprolactone mono (meth) acrylate, cyclohexyl (meth) acrylate, 2- (2-ethoxyethoxy) ethyl (meth) acrylate, stearyl (meth) acrylate, diethylene glycol monobutyl ether (meth) acrylate, lauryl (meth) acrylate, isodecyl (meth) acrylate, isooctyl (meth) acrylate, octyl/decyl (meth) acrylate, hydroxyethyl (meth) acrylate, tridecyl (meth) acrylate, caprolactone (meth) acrylate, ethoxylated (4) nonylphenol (meth) acrylate, methoxypolyethylene glycol (350) mono (meth) acrylate, methoxypolyethylene glycol (550) mono (meth) acrylate, phenoxyethyl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, methylphenoxyethyl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, tribromophenyl ethoxylated (meth) acrylate, 2-phenoxyethyl (meth) acrylate, an ethylene oxide adduct of 2-phenoxyethyl (meth) acrylate, a propylene oxide adduct of ethylene oxide, a propylene, At least one compound selected from the group consisting of phenoxydiethylene glycol (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 3-methacryloxymethylepoxyhexane, and 3- (meth) acryloyloxymethylepoxyhexane.
The monofunctional acrylic compound (a3) preferably contains a compound having an alicyclic structure. The compound having an alicyclic structure contains, for example, at least one compound selected from cyclohexyl (meth) acrylate, dicyclopentyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, 3, 5-trimethylcyclohexyl (meth) acrylate, and 4-t-butylcyclohexyl (meth) acrylate.
The monofunctional acrylic compound (A3) preferably further contains a compound (a31) represented by the following formula (10). In this case, the viscosity of the composition (X) can be easily reduced, and the sealing material 5 made of the composition (X) can be easily provided with adhesion to a member made of an inorganic material such as the passivation layer 6. Further, the compound (a31) has low viscosity but is not volatile. Therefore, even when the composition (X) is stored, the composition (X) is less likely to undergo a change in composition due to volatilization of the monofunctional acrylic compound (a 3).
[ chemical formula 1]
In the formula (10), R0Is H or methyl. X is a single bond or a divalent hydrocarbon group. R1～R11Are each H, alkyl or-R12-OH，R12Is alkylene and R1～R11At least one of which is alkyl or-R12-OH。R1～R11Are not chemically bonded to each other.
When X is a divalent hydrocarbon group, the number of carbon atoms of X is preferably 1 or more and 5 or less, and more preferably 1 or more and 3 or less. Divalent hydrocarbon groups are, for example, methylene, ethylene or propylene. X is particularly preferably a single bond or a methylene group. In this case, the compound (a31) has advantages of a small molecular weight and a low viscosity.
At R1～R11In the case where at least one of the alkyl groups is an alkyl group, the number of carbon atoms of the alkyl group is preferably 1 to 8. Alkyl is for example methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl. The alkyl group may be linear or branched. That is, for example, when the alkyl group is a butyl group, the butyl group may be a tert-butyl group, a n-butyl group, or a sec-butyl group. When the alkyl group is a hexyl group, the hexyl group may be a tert-hexyl group, an n-hexyl group, or a sec-hexyl group. In the case where the alkyl group is octyl, the octyl group may be, for example, tert-octyl. Alkyl is particularly preferably methyl or tert-butyl. In this case, the compound (a31) has advantages of a small molecular weight and a low viscosity.
In the formula (10), it is preferable that an alkyl group or-R is bonded only to the 4-position of the cyclohexane ring12-OH. That is, it is preferable to use R1～R11In, R6And R7At least one of which is alkyl or-R12-OH and each of the others is H. Particularly preferably in R1～R11In (1), only R6Is alkyl or-R12-OH and each of the others is H. In this case, the compound represented by formula (10) can have good reactivity, and particularly, it is easy to impart adhesion to the sealing material 5 with respect to a member made of an inorganic material. This is considered to be because the cyclohexane ring in the compound represented by the formula (10) has a boat-shaped three-dimensional conformation, and the bulky alkyl group or-R at the 4-position12the-OH is easily located at approximately the equatorial position. It is considered that the reactivity of the (meth) acryloyl group in the compound represented by formula (10) can be improved by the compound represented by formula (10) having such a structure. In addition, if the compound represented by formula (10) has such a structure, the compound represented by formula (10) can increase the free volume in the sealing material 5. Therefore, it is considered that the interface free energy between the sealing material 5 and the inorganic material member is likely to be small, and thus the sealing material 5 and the inorganic material portion are likely to be smallThe adhesiveness of the material is easily increased. Alkyl or-R12The larger the-OH volume, the alkyl group or-R12The easier the-OH is at approximately the equatorial position. From this viewpoint, alkyl or-R12The more the number of carbon atoms of-OH is, the more preferable is an alkyl group or-R12-OH has a branched chain. For example, preferably alkyl or-R12-OH is tert-butyl.
In the formula (10), it is also preferable that an alkyl group or-R is bonded to only the 3-and 5-positions of the cyclohexane ring, respectively12-OH. That is, it is preferable to use R1～R11In, R4And R5At least one of which is alkyl or-R12-OH，R8And R9At least one of which is alkyl or-R12-OH and each of the others is H. More preferably in R1～R11In (1), only R4And R5One of them is alkyl or-R12-OH，R8And R9At least one of which is alkyl or-R12-OH and each of the others is H. More preferably in R1～R11In, R4And R5At least one of which is alkyl or-R12-OH, only R8And R9One of them is alkyl or-R12-OH and each of the others is H. In this case, the compound represented by formula (10) can also have good reactivity, and particularly, it is easy to impart adhesion to the sealing material 5 with respect to a member made of an inorganic material. This is considered to be because the cyclohexane ring in the compound represented by the formula (10) has a boat-shaped three-dimensional conformation, and the 3-position and 5-position each have a bulky alkyl group or-R12the-OH is easily located at approximately the equatorial position. Therefore, it is considered that an alkyl group or-R is bonded to only the 4-position of the cyclohexane ring12Similarly to the case of — OH, the reactivity of the (meth) acryloyl group in the compound represented by formula (10) is improved, and the adhesion between the sealing material 5 and the member made of an inorganic material is likely to be increased. Alkyl or-R12The larger the-OH volume, the alkyl group or-R12The easier the-OH is at approximately the equatorial position. From this viewpoint, alkyl or-R12The more the number of carbon atoms of-OH is, the more preferable is an alkyl group or-R12-OH has a branched chain. For example, preferably alkyl or-R12-OH is tert-butyl.
At R1～R11At least one of which is-R12In the case of-OH, R12The number of carbon atoms of (b) is preferably 1 to 5, more preferably 1 to 3. R12For example methylene, ethylene or propylene. R12Methylene is particularly preferred. In this case, the compound (a31) has advantages of a small molecular weight and a low viscosity.
In the formula (10), R is particularly preferred1～R11Each is H or alkyl, and R1～R11At least one of which is an alkyl group. In this case, the compound represented by formula (10) can have a particularly low viscosity, and therefore, the composition (X) can have a particularly low viscosity. Therefore, the composition (X) is particularly easily molded by an ink jet method.
The compound (a31) preferably contains at least one compound selected from the group consisting of a compound represented by the following formula (11), a compound represented by the following formula (12), and a compound represented by the following formula (13).
[ chemical formula 2]
Particularly preferably, the monofunctional acrylic compound (a3) contains at least one of the compound represented by formula (11) and the compound represented by formula (12). In this case, it is particularly easy to lower the viscosity of the composition (X), to increase the glass transition temperature of the sealing material 5, and to improve the adhesion between the sealing material 5 and the inorganic material member. Further, since the compound represented by formula (11) and the compound represented by formula (12) are less likely to volatilize, the storage stability of the composition (X) is likely to be improved.
The monofunctional acrylic compound (a3) preferably further contains a compound having a cyclic ether structure. The number of cyclic elements of the cyclic ether structure in the compound having a cyclic ether structure is preferably 3 or more, and more preferably 3 or more and 4 or less. The number of carbon atoms contained in the cyclic ether structure is preferably 2 or more and 9 or less, and more preferably 2 or more and 6 or less. The compound having a cyclic ether structure contains, for example, at least one compound selected from the group consisting of 3-methacryloxymethylcyclohexene oxide and 3-acryloxymethylcyclohexene oxide.
The monofunctional acrylic compound (A3) preferably contains at least one compound having a viscosity of 20 mPas or less at 25 ℃. In this case, the viscosity of the composition (X) can be reduced.
The monofunctional acrylic compound (a3) preferably contains at least one compound having a glass transition temperature of 80 ℃ or higher. In this case, the cured product of the composition (X) can have a high glass transition temperature. The monofunctional acrylic compound (a3) more preferably contains at least one compound having a glass transition temperature of 90 ℃ or higher, and still more preferably contains at least one compound having a glass transition temperature of 100 ℃ or higher.
The monofunctional acrylic compound (A3) preferably contains at least one compound having a boiling point of 200 ℃ or higher. In this case, the monofunctional acrylic compound (a3) is less likely to decrease the storage stability of the composition (X). The monofunctional acrylic compound (A3) preferably further contains at least one compound having a boiling point of 250 ℃ or higher.
The monofunctional acrylic compound (A3) particularly preferably contains at least one compound having a viscosity of 20 mPas or less at 25 ℃ and a glass transition temperature of 80 ℃ or higher. The monofunctional acrylic compound (A3) preferably contains at least one compound having a viscosity of 20 mPas or less at 25 ℃ and a boiling point of 200 ℃ or more. The monofunctional acrylic compound (A3) preferably contains at least one compound having a glass transition temperature of 80 ℃ or higher and a boiling point of 200 ℃ or higher. The monofunctional acrylic compound (A3) particularly preferably contains at least one compound having a viscosity of 20 mPas or less at 25 ℃, a glass transition temperature of 80 ℃ or more, and a boiling point of 200 ℃ or more.
The monofunctional acrylic compound (A3) is particularly preferably one containing at least one compound selected from the group consisting of isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, 3, 5-trimethylcyclohexyl (meth) acrylate and 4-t-butylcyclohexyl (meth) acrylate. Isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, 3, 5-trimethylcyclohexyl (meth) acrylate, and 4-t-butylcyclohexyl (meth) acrylate have a high glass transition temperature, a low viscosity, and a high boiling point, and therefore, the properties of the composition (X), the curing agent, and the sealing material 5 can be particularly improved.
The acrylic compound (a) preferably further contains at least one compound selected from the group consisting of a compound (a41) having silicon in the molecular skeleton, a compound (a42) having phosphorus in the molecular skeleton, and a compound (a43) having nitrogen in the molecular skeleton. In this case, the adhesion between the cured product and the inorganic material member and the sealing material 5 is improved. Therefore, a gap is less likely to be formed between the sealing material 5 and the passivation layer 6, and the penetration of moisture into the organic EL element 4 through the gap is less likely to occur.
The compound (a41), the compound (a42), and the compound (a43) are defined by the kind of atoms present in the molecular skeleton. Therefore, the compound contained in each of the polyfunctional acrylic compound (a2) and the monofunctional acrylic compound (A3) and the compound contained in each of the compound (a41), the compound (a42), and the compound (a43) can be repeated.
The compound (A41) contains, for example, at least one compound selected from the group consisting of 3- (trimethoxysilyl) propyl acrylate (e.g., product No. KBM5103 from shin-Etsu chemical industries, Ltd.) and an alkoxysilane oligomer containing a (meth) acrylic group (e.g., product No. KR-513 from shin-Etsu chemical industries, Ltd.). However, since the boiling point of 3- (trimethoxysilyl) propyl acrylate is 260 ℃, in the case where the acrylic compound (A) contains 3- (trimethoxysilyl) propyl acrylate, the percentage of 3- (trimethoxysilyl) propyl acrylate to the acrylic compound (A) needs to be 10% by mass or less.
The compound (A42) includes, for example, an acid phosphonoxy (meth) acrylate such as an acid phosphonoxy polyoxypropylene glycol monomethacrylate.
The compound (a43) contains, for example, at least one compound selected from acryloyl morpholine, diethyl acrylamide, dimethylaminopropyl acrylamide and pentamethylpiperidine methacrylate.
When the acrylic compound (a) contains at least one compound selected from the group consisting of the compound (a41), the compound (a42), and the compound (a43), the percentage of the total amount of the compound (a41), the compound (a42), and the compound (a43) to the acrylic compound (a) is preferably 0.5% by mass or more and 20% by mass or less, and more preferably 1% by mass or more and 15% by mass or less.
The composition (X) may further contain a radical polymerizable compound (E) other than the acrylic compound (a). The radically polymerizable compound (E) may contain either or both of a polyfunctional radically polymerizable compound (E1) having two or more radically polymerizable functional groups in one molecule and a monofunctional radically polymerizable compound (E2) having only one radically polymerizable functional group in one molecule. The amount of the radical polymerizable compound (E) is, for example, 10% by mass or less relative to the total amount of the acrylic compound (a) and the radical polymerizable compound (E). The polyfunctional radical polymerizable compound (E1) may contain, for example, at least one compound selected from the group consisting of an aromatic urethane oligomer having 2 or more ethylenic double bonds in one molecule, an aliphatic urethane oligomer, an epoxy acrylate oligomer, a polyester acrylate oligomer, and other special oligomers. The monofunctional radical polymerizable compound (E2) contains at least one compound selected from the group consisting of, for example, N-vinylformamide, vinylcaprolactam, vinylpyrrolidone, phenylglycidyl ether, p-tert-butylphenyl glycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, 1, 2-epoxybutane, 1, 3-butadiene monooxide, 1, 2-epoxydodecane, epichlorohydrin, 1, 2-epoxydecane, styrene oxide, epoxyhexane, 3-vinylcyclohexene oxide, 4-vinylcyclohexene oxide, N-vinylpyrrolidone and N-vinylcaprolactam.
The photopolymerization initiator (B) is not particularly limited as long as it is a compound that generates radical species upon irradiation with ultraviolet rays. The photopolymerization initiator (B) contains, for example, at least one compound selected from aromatic ketones, acylphosphine oxide compounds, aromatic onium salt compounds, organic peroxides, sulfur compounds (thioxanthone compounds, thiophenyl-containing compounds, and the like), hexaarylbiimidazole compounds, ketoxime ester compounds, borate ester compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds. The amount of the photopolymerization initiator (B) is, for example, 1 part by weight or more and 10 parts by weight or less with respect to 100 parts by weight of the composition (X).
The photopolymerization initiator (B) may contain a sensitizer as a part of the photopolymerization initiator (B). The sensitizer promotes a radical generating reaction of the photopolymerization initiator (B), improves reactivity of radical polymerization, and increases crosslinking density. The sensitizer may contain, for example, at least one compound selected from the group consisting of 9, 10-dibutoxyanthracene, 9-hydroxymethylanthracene, thioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2-chlorothioxanthone, 2, 4-diethylthioxanthone, anthraquinone, 1, 2-dihydroxyanthraquinone, 2-ethylanthraquinone, 1, 4-diethoxynaphthalene, p-dimethylaminoacetophenone, p-diethylaminoacetophenone, p-dimethylaminobenzophenone, p-diethylaminobenzophenone, 4 '-bis (dimethylamino) benzophenone, 4' -bis (diethylamino) benzophenone, p-dimethylaminobenzaldehyde, and p-diethylaminobenzaldehyde.
The content of the sensitizer in the composition (X) is, for example, 0.1 part by mass or more and 5 parts by mass or less, and preferably 0.1 part by mass or more and 3 parts by mass or less, with respect to 100 parts by mass of the solid content of the composition (X). If the content of the sensitizer is within such a range, the composition (X) can be cured in air, and it is not necessary to cure the composition (X) in an inert atmosphere such as a nitrogen atmosphere.
The composition (X) may contain a polymerization accelerator in addition to the photopolymerization initiator (B). The polymerization accelerator contains an amine compound such as ethyl p-dimethylaminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, methyl p-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, butoxyethyl p-dimethylaminobenzoate.
The composition (X) may further contain a moisture absorbent (D). If the composition (X) contains the moisture absorbent (D), the cured product of the composition (X) and the sealing material 5 can have moisture absorption properties. Therefore, the sealing material 5 can make the moisture less likely to enter the organic EL element 4 in the organic EL light-emitting device 1. The average particle diameter of the moisture absorbent (D) is preferably 200nm or less. In this case, the cured product can have high transparency.
The moisture absorbent (D) is preferably an inorganic particle having moisture absorption properties, and preferably contains at least one component selected from zeolite particles, silica gel particles, calcium chloride particles, and titanium oxide nanotube particles, for example. The moisture absorbent (D) particularly preferably contains zeolite particles.
The zeolite particles having an average particle diameter of 200nm or less can be produced by, for example, pulverizing a usual industrial zeolite. In the case of producing zeolite particles, the zeolite may be pulverized and then crystallized by hydrothermal synthesis or the like, and in this case, the zeolite particles can have particularly high hygroscopicity. Examples of such a method for producing zeolite particles are disclosed in japanese patent application laid-open nos. 2016 and 69266 and 2013 and 049602.
When the composition (X) contains the moisture absorbent (D), the proportion of the moisture absorbent (D) to the total amount of the composition (X) is preferably 1 mass% or more and 20 mass% or less. When the proportion of the moisture absorbent (D) is 1% by mass or more, the cured product can have particularly high moisture absorption. In addition, if the proportion of the moisture absorbent (D) is 20% by mass or less, the viscosity of the composition (X) can be particularly reduced, and the composition (X) can also have a sufficiently low viscosity to the extent that it can be applied by an ink jet method. The proportion of the moisture absorbent (D) is more preferably 3% by mass or more, and particularly preferably 5% by mass or more. The proportion of the moisture absorbent (D) is more preferably 15% by mass or less, and particularly preferably 13% by mass or less.
When the composition (X) contains the moisture absorbent (D), the composition (X) preferably further contains the dispersant (E). In this case, the dispersant (E) can improve the dispersibility of the moisture absorbent (D) in the composition (X). Therefore, in the composition (X), an increase in viscosity and a decrease in storage stability due to the moisture absorbent (D) are less likely to occur.
The dispersant (E) is a surfactant that can be adsorbed to the particles. The dispersant (E) has an adsorption group (also commonly referred to as an anchor) that can be adsorbed to a particle, and a molecular skeleton (also commonly referred to as a tail) that is adsorbed to the particle by the adsorption group and is attached to the particle. The dispersant (E) contains, for example, at least one component selected from the following dispersants: an acrylic dispersant having an acrylic molecular chain as a tail, a urethane dispersant having a urethane molecular chain as a tail, and a polyester dispersant having a polyester molecular chain as a tail. The adsorbing group contains, for example, at least one of a basic polar functional group and an acidic polar functional group. The basic polar functional group includes, for example, at least one group selected from an amino group, an imino group, an amide group, an imide group, and a nitrogen-containing heterocyclic group. The acidic polar functional group contains, for example, at least one group selected from a carboxyl group and a phosphate group. The dispersant (E) may contain, for example, at least one compound selected from Solsperse series manufactured by Lubrizo1 K.K., DISPERBYK series manufactured by BYK-Chemie Japan K.K., and AJISPER series manufactured by Ajine-Techno K.K.K.K.K.K.K.K.K.K.
When the composition (X) contains the moisture absorbent (D), the amount of the dispersant (E) is preferably 5 parts by mass or more and 60 parts by mass or less with respect to the moisture absorbent (D). When the amount of the dispersant (E) is 5 parts by mass or more, the function of the dispersant (E) can be effectively exhibited, and when the amount is 60 parts by mass or less, the free molecules of the dispersant (E) in the sealing material 5 can be suppressed from inhibiting adhesion between the sealing material 5 and a member made of an inorganic material. The amount of the dispersant (D) is more preferably 15 parts by mass or more, still more preferably 50 parts by mass or less, still more preferably 40 parts by mass or less, and particularly preferably 30 parts by mass or less.
The composition (X) preferably contains no solvent. In this case, it is not necessary to dry the composition (X) and volatilize the solvent when a cured product is produced from the composition (X). In addition, the storage stability of the composition (X) is further improved.
The composition (X) can be prepared by mixing the above components. The composition (X) is preferably liquid at 25 ℃.
3. Method for producing sealing material and method for producing organic EL light-emitting device
A method for producing the sealing material 5 using the composition (X) and a method for producing the organic EL light-emitting device 1 will be described.
In the present embodiment, it is preferable that the sealing material 5 is prepared by molding the composition (X) by an ink jet method and then curing the composition (X) by irradiating it with ultraviolet light. In the present embodiment, the composition (X) can be applied by an ink jet method to be molded.
When the composition (X) is applied by an ink jet method, if the composition (X) has a sufficiently low viscosity at room temperature, for example, a viscosity of 30mPa · s or less, particularly 15mPa · s or less at 25 ℃, the composition (X) can be applied by an ink jet method without heating and molded.
In the case where the composition (X) has a property of being reduced in viscosity by heating, the composition (X) may be applied by an ink jet method after heating the composition (X) to be molded. When the viscosity of the composition (X) at 40 ℃ is 30 mPas or less, particularly 15 mPas or less, the viscosity of the composition (X) can be reduced by heating the composition (X) only slightly, and the composition (X) having a reduced viscosity can be discharged by an ink jet method. The heating temperature of the composition (X) is, for example, 20 ℃ or more and 50 ℃ or less.
More specifically, for example, the support substrate 2 is first prepared. For example, partition walls 7 are formed on one surface of the support substrate 2 by photolithography using a photosensitive resin material. Next, a plurality of organic EL elements 4 are provided on one surface of the support substrate 2. The organic EL element 4 can be produced by an appropriate method such as a vapor deposition method or a coating method. The organic EL element 4 is particularly preferably produced by an application method such as an ink jet method. Thereby, the element array 9 is produced on the support substrate 2.
Next, a first passivation layer 61 is provided on the element array 9. The first passivation layer 61 can be formed by an evaporation method such as a plasma CVD method.
Next, the composition (X) is molded on the first passivation layer 61 by, for example, an ink-jet method, thereby producing a coating film. If the ink jet method is applied to both the formation of the organic EL element 4 and the application of the composition (X), the production efficiency of the organic EL light-emitting device 1 can be particularly improved. Next, the coating film is irradiated with ultraviolet rays and cured to produce the sealing material 5. The thickness of the sealing material 5 is, for example, 5 μm or more and 50 μm or less.
Next, a second passivation layer 62 is provided on the sealing material 5. The second passivation layer 62 can be formed by an evaporation method such as a plasma CVD method.
Next, an ultraviolet-curable resin material is provided on one surface of the support substrate 2 so as to cover the second passivation layer 62, and then the transparent substrate 3 is stacked on the resin material. The transparent substrate 3 is, for example, a glass substrate or a transparent resin substrate.
Next, ultraviolet rays are irradiated from the outside to the transparent substrate 3. The ultraviolet rays pass through the transparent substrate 3 and reach the ultraviolet-curable resin material. Thereby, the ultraviolet-curable resin material is cured, and the second sealing material 52 is produced.
Examples
1. Preparation of the composition
The compositions of the examples and comparative examples were prepared by mixing the ingredients shown in the following table.
The details of the components shown in the table are as follows. The viscosity of each of the following components was measured at 25 ℃ and a shear rate of 1000s using a rheometer (model DHR-2 manufactured by Anton Paar Japan)-1The value measured under the conditions of (1).
(1) Acrylic acid compound
-KBM 5103: 3- (trimethoxysilyl) propyl acrylate, which is a monofunctional acrylic compound having a silicon atom, has a viscosity of 4 mPas, a refractive index of 1.427, and a boiling point of 260, and is manufactured by KBM5103, a product of shin-Etsu chemical industries, Ltd.
-KR 513: the acrylic group-containing alkoxysilane oligomer which is a 3-or more-functional acrylic compound having a silicon atom has a viscosity of 50 mPas, a refractive index of 1.427, and a boiling point of 300 ℃ or higher.
-LIGHT ESTER P-2M: 2-methacryloyloxyethyl acid phosphate, product name LIGHT ESTER P-2M, viscosity 800 mPas, refractive index 1.4673, boiling point 300 or more, manufactured by Kyoeisha chemical Co., Ltd.
-ACMO: acryloylmorpholine, manufactured by KJ Chemical, viscosity 12 mPas, glass transition temperature 145 ℃.
-3 PG: tri (propylene glycol) dimethacrylate, a bifunctional acrylic compound, was manufactured by Mizhoura chemical industries, product No. 3PG, viscosity 13 mPas, glass transition temperature-8 ℃, refractive index 1.450, and boiling point 400 ℃.
-APG 200: tri (propylene glycol) diacrylate as a bifunctional acrylic compound having a viscosity of 12 mPas, a glass transition temperature of 55 to 62 ℃, a refractive index of 1.449 and a boiling point of 295 ℃ manufactured by Newzhongcun chemical industries, Ltd.
-SR 297: 1, 3-butanediol dimethacrylate as a bifunctional acrylic compound was manufactured by Sartomer corporation, product No. SR297, viscosity 7 mPa.s, glass transition temperature 85 ℃, refractive index 1.449, boiling point 290 ℃.
-EBECRYL 145: propylene oxide-modified neopentyl glycol diacrylate as a bifunctional acrylic compound, product No. EBECRYL145 manufactured by DAICEL ALLNEX, viscosity 20 mPas, glass transition temperature 60 ℃, refractive index 1.459, and boiling point 408 ℃.
-BD: 1, 4-butanediol dimethacrylate as a bifunctional acrylic compound, manufactured by Mizhongcun chemical industries, viscosity 7 mPas, glass transition temperature 55 ℃, refractive index 1.456, boiling point 280 ℃.
-SR 351S: trimethylolpropane triacrylate, a trifunctional acrylic compound, has a viscosity of 106 mPas, a glass transition temperature of 62 ℃, a refractive index of 1.472, a boiling point of 300 ℃ or higher, product number SR351S, manufactured by Sartomer corporation.
-SR350 NS: trimethylolpropane trimethacrylate, a trifunctional acrylic compound, has a viscosity of 44 mPas, a glass transition temperature of 27 ℃, a refractive index of 1.470 and a boiling point of 300 ℃ or higher, manufactured by Sartomer corporation, product No. SR350 NS.
-SR295 NS: pentaerythritol tetraacrylate, a tetrafunctional acrylic compound, has a viscosity of 342 mPas, a glass transition temperature of 103 ℃, a refractive index of 1.485 and a boiling point of 300 ℃ or higher, manufactured by Sartomer corporation, product No. SR295 NS.
-SR210 NS: polyethylene glycol 200 dimethacrylate, viscosity 15 mPas, glass transition temperature-9 ℃, refractive index 1.460, boiling point 350 ℃, manufactured by Sartomer company, product number SR210 NS.
-VEEA: 2- (2-ethyleneoxyethoxy) ethyl acrylate as a bifunctional radical polymerizable compound, having a viscosity of 4 mPas, a glass transition temperature of 40 ℃, a boiling point of 260 ℃ and prepared by Japanese catalyst.
-IBXA: isobornyl acrylate, which is a monofunctional acrylic compound, has a glass transition temperature of 97 ℃, a viscosity of 8mPa · s, a boiling point of 260 ℃, manufactured by Osaka organic Chemicals.
-FA-513 AS: dicyclopentyl acrylate AS a monofunctional acrylic compound had a glass transition temperature of 120 ℃, a viscosity of 13 mPas, a boiling point of 275 ℃ and a product number FA-513AS manufactured by Hitachi chemical Co.
(2) Photopolymerization initiator
-Irgacure 184: 1-hydroxy-cyclohexyl-phenyl-ketone, product name Irgacure184, from BASF.
Irgacure TPO: 2, 4, 6-trimethylbenzoyl-diphenyl-phosphine oxide, product name Irgacure TPO from BASF.
2. Evaluation test
The following evaluation tests were carried out for examples and comparative examples. The results are shown in the table.
(1) Transmittance of light
A coating film was formed by coating the composition with an LED-UV irradiator (peak wavelength: 365nm) made by Matsushita electric Co., Ltd., at a concentration of about 50mW/cm2The coating film was irradiated with ultraviolet light for 30 seconds to be photocured, thereby producing a film having a thickness of 10 μm. The total light transmittance of the film was measured in accordance with JIS K7361-1.
(2) Adhesion after moisture absorption
Two quartz glass plates (size 76 mm. times.52 mm. times.1 mm) were each coated on their surface by a plasma CVD methodA silicon nitride film having a thickness of 1 μm was formed to obtain two substrates. A coating film having a thickness of 200 μm is formed by applying the composition to the surface of the silicon nitride film of one substrate, and the silicon nitride film of the other substrate is superposed on the coating film. Next, an LED-UV irradiator (peak wavelength: 365nm) manufactured by Matsua electric corporation was used at about 50mW/cm2The coating film was cured by irradiating ultraviolet rays for 30 seconds under the conditions of (1). Thus, a test piece was obtained.
After the test piece was exposed to an atmosphere of 85 ℃ and 85RH, the interface between the coating film and the silicon nitride film was observed with a microscope. The results were evaluated as follows. In this test, the higher the adhesion between the coating film and the silicon nitride film, and the more the coating film is less likely to absorb moisture, the more the coating film is less likely to be peeled off from the silicon nitride film.
A: even if the coating film is exposed to the atmosphere for 96 hours, a portion of the coating film having an area of 5 or more is in close contact with the silicon nitride film.
B: even if the coating film is exposed to the atmosphere for 48 hours, a portion of the coating film having an area of 5 or more is not peeled from the silicon nitride film, and after the exposure for 96 hours, a portion of the coating film having an area of 5 or more is peeled from the silicon nitride film.
C: even if the coating film is exposed to the atmosphere for 24 hours, a portion of the coating film having an area of 5 or more is not peeled from the silicon nitride film, and after the exposure for 48 hours, a portion of the coating film having an area of 5 or more is peeled from the silicon nitride film.
D: after exposure to the atmosphere for 24 hours, a portion of the coating film having an area of 5 or more was peeled off from the silicon nitride film.
(3) Volatility
The composition was allowed to stand at 20 ℃ under an argon atmosphere (dew point temperature-70 ℃) for 24 hours. The proportion of weight loss of the resulting composition was determined. The weight loss was evaluated as "A" when the weight loss was 0.5% or less, as "B" when the weight loss was 0.5 to 1%, and as "C" when the weight loss was 1% or more.
(4) Viscosity of the oil
The shear rate was 1000 seconds at 25 ℃ using a rheometer (model DHR-2 manufactured by Anton Paar Japan)-1Under the conditions of (1) measuring the compositionViscosity.
(5) Ink-jet property
The composition was put into a cartridge of an ink jet printer (gloss, form MH2420), and after confirming that the composition in the cartridge could be discharged from a nozzle in the ink jet printer, the composition was discharged from the nozzle to continuously print a test pattern. As a result, the case where the composition could be discharged for 1 hour and the discharge operation was stable was evaluated as "a", the case where the composition could be discharged for 1 hour but the discharge operation was intermittently unstable was evaluated as "B", and the case where the nozzle was clogged without 1 hour from the start of discharge and the composition could not be discharged was evaluated as "C".
(6) Glass transition temperature
A coating film was prepared by coating the composition, and the coating film was irradiated with an LED-UV irradiator (peak wavelength: 365nm) made by Matsushita electric Co., Ltd. at a concentration of about 50mW/cm2A film having a thickness of 200 μm was produced for 30 seconds under the conditions of (1). The glass transition temperature of a sample cut out from the film was measured using a viscoelasticity measuring apparatus (model DMA7100, manufactured by Hitachi High-Tech Science Co.).
(7) Evaluation of outgassing
The outgas generated when the cured product of the composition was heated was sampled by the headspace method and measured by gas chromatography. A headspace vial was charged with 100mg of the composition, and the composition was irradiated with an LED-UV irradiator (peak wavelength: 365nm) manufactured by Song electric corporation, and the cumulative light amount was 1500mJ/cm2The composition was cured by irradiation with ultraviolet rays under the conditions of (1), the vial was sealed, and after heating at 80 ℃ for 30 minutes, the gas phase portion in the vial was introduced into a gas chromatograph for analysis. As a result, the gas generated was evaluated as "a" when it was 300ppm or less, as "B" when it exceeded 300ppm and was less than 500ppm, and as "C" when it was 500ppm or more.
[ Table 1]
[ Table 2]
Claims (10)
1. An ultraviolet-curable resin composition for sealing an organic EL element, comprising an acrylic compound A and a photopolymerization initiator B,
the acrylic compound A contains an acrylic compound A1 having a structure represented by the following formula (1) and a boiling point of 270 ℃ or higher,
CH2＝CR1-COO-(R3-O)n-CO-CR2＝CH2…(1)
in the formula (1), R1And R2Each is hydrogen or methyl, n is an integer of 1 or more, R3Is an alkylene group having 3 or more carbon atoms, and when n is 2 or more, a plurality of R's in one molecule3Optionally the same or different from each other,
the percentage of the acrylic compound A1 to the acrylic compound A is 50% by mass or more,
the acrylic compound A does not contain a compound having a boiling point of 260 ℃ or lower, or the proportion of a compound having a boiling point of 260 ℃ or lower in the acrylic compound A is 10% by mass or lower.
2. The ultraviolet-curable resin composition according to claim 1, wherein the acrylic compound A1 has a viscosity of 25 mPas or less at 25 ℃.
3. The ultraviolet-curable resin composition according to claim 1 or 2, which is molded by an ink jet method.
4. The ultraviolet-curable resin composition according to any one of claims 1 to 3, wherein the acrylic compound A further contains a compound A21 having three or more (meth) acryloyl groups in one molecule.
5. The ultraviolet-curable resin composition according to any one of claims 1 to 4, wherein a cured product thereof has a glass transition temperature of 80 ℃ or higher.
6. The ultraviolet-curable resin composition according to any one of claims 1 to 5, wherein the acrylic compound A further contains at least one compound selected from a compound A41 having silicon in a molecular skeleton, a compound A42 having phosphorus in a molecular skeleton, and a compound A43 having nitrogen in a molecular skeleton.
7. The ultraviolet-curable resin composition according to any one of claims 1 to 6, wherein the percentage of a component having a boiling point of 270 ℃ or higher in the acrylic compound A is 80% by mass or higher.
8. A method for manufacturing an organic EL light-emitting device having an organic EL element and a sealing material covering the organic EL element,
the method for producing an organic EL light-emitting device includes molding the ultraviolet-curable resin composition according to any one of claims 1 to 7 by an ink-jet method, and then irradiating ultraviolet rays to the ultraviolet-curable resin composition to cure the resin composition, thereby producing the sealing material.
9. The method for manufacturing an organic EL light-emitting device according to claim 8, wherein the ultraviolet-curable resin composition is heated and then molded by an inkjet method.
10. An organic EL light-emitting device comprising an organic EL element and a sealing material covering the organic EL element, wherein the sealing material is a cured product of the ultraviolet-curable resin composition according to any one of claims 1 to 7.
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| JP2018-182923 | 2018-09-27 | ||
| PCT/JP2019/034039 WO2020066455A1 (en) | 2018-09-27 | 2019-08-30 | Uv-curable resin composition, method for manufacturing organic el light emission device, and organic el light emission device |
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| JP6818761B2 (en) | 2016-10-14 | 2021-01-20 | デンカ株式会社 | Composition |
| JP6369790B1 (en) | 2017-08-09 | 2018-08-08 | パナソニックＩｐマネジメント株式会社 | Ultraviolet curable resin composition, organic EL light emitting device manufacturing method, and organic EL light emitting device |
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2018
- 2018-09-27 JP JP2018182923A patent/JP7281663B2/en active Active
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2019
- 2019-08-30 WO PCT/JP2019/034039 patent/WO2020066455A1/en active Application Filing
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| JP7281663B2 (en) | 2023-05-26 |
| WO2020066455A1 (en) | 2020-04-02 |
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