CN103732658A - Sheet-shaped epoxy resin composition, and sealing sheet containing same - Google Patents
Sheet-shaped epoxy resin composition, and sealing sheet containing same Download PDFInfo
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- CN103732658A CN103732658A CN201280040160.8A CN201280040160A CN103732658A CN 103732658 A CN103732658 A CN 103732658A CN 201280040160 A CN201280040160 A CN 201280040160A CN 103732658 A CN103732658 A CN 103732658A
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- epoxy resin
- sheet
- composition epoxy
- sheet composition
- organic
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- 239000000203 mixture Substances 0.000 title claims abstract description 309
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 279
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 276
- 238000007789 sealing Methods 0.000 title claims description 60
- 238000003860 storage Methods 0.000 claims abstract description 34
- 239000000463 material Substances 0.000 claims description 48
- 239000004593 Epoxy Substances 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 29
- 239000000758 substrate Substances 0.000 claims description 29
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 26
- 229930185605 Bisphenol Natural products 0.000 claims description 25
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000012528 membrane Substances 0.000 claims description 18
- 230000001681 protective effect Effects 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000003700 epoxy group Chemical group 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 10
- 238000007731 hot pressing Methods 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 7
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000011342 resin composition Substances 0.000 abstract description 13
- 230000003287 optical effect Effects 0.000 abstract description 8
- 238000010348 incorporation Methods 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 45
- 229920005989 resin Polymers 0.000 description 44
- 239000011347 resin Substances 0.000 description 44
- 239000002585 base Substances 0.000 description 43
- 230000000052 comparative effect Effects 0.000 description 27
- 239000011521 glass Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- 239000002966 varnish Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 16
- 230000035699 permeability Effects 0.000 description 16
- 239000000126 substance Substances 0.000 description 14
- -1 amine compound Chemical class 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 230000006978 adaptation Effects 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 238000010030 laminating Methods 0.000 description 10
- 238000001291 vacuum drying Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 238000010023 transfer printing Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000003475 lamination Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000004566 IR spectroscopy Methods 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000012216 screening Methods 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000005030 aluminium foil Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 150000004693 imidazolium salts Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 230000005477 standard model Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000009998 heat setting Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- WYYQKWASBLTRIW-UHFFFAOYSA-N 2-trimethoxysilylbenzoic acid Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1C(O)=O WYYQKWASBLTRIW-UHFFFAOYSA-N 0.000 description 1
- BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- DQFMPTUTAAIXAN-UHFFFAOYSA-N 4,4-dimethyl-1h-imidazol-5-one Chemical compound CC1(C)NC=NC1=O DQFMPTUTAAIXAN-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical class CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 238000007601 warm air drying Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/80—Constructional details
- H10K59/87—Passivation; Containers; Encapsulations
- H10K59/873—Encapsulations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Electroluminescent Light Sources (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
Abstract
The objective of the present invention is to provide a resin composition that is for a sheet, has superior adhesion to optical elements and the like and transparency after curing, and resists incorporation of air at the interface between an element and the resin composition for a sheet during thermocompression bonding. The sheet-shaped epoxy resin composition contains (A) an epoxy resin having a weight average molecular weight of 2000 to 1*105 and (B) a curing accelerator, and the storage elastic modulus (G'(50)) at 50 DEG C and the storage elastic modulus (G'(80)) at 80 DEG C satisfies G'(50)/G'(80)<11 and(G'(80)) is 2500Pa-5*105 Pa.
Description
Technical field
The sheet for sealing that the present invention relates to sheet composition epoxy resin and contain this sheet composition epoxy resin etc.Particularly relate to the sheet composition epoxy resin and the sheet for sealing that are suitable for the Optical devices such as OLED display.
Background technology
In optical device, organic EL, due to the consistence excellence of low power consumption, high visual angle, polarized light property, therefore expects to be applied to means of illumination, indicating meter of future generation.But organic EL exists because of easily deteriorated problem of the moisture in atmosphere, oxygen.Therefore, organic EL is sealed and is used by containment member, but urgently waits in expectation for making the sealing material of the containment member that Water Vapour Permeability is lower.
As the sealing material of optical element or electronic component, propose: the composition (for example, with reference to patent documentation 1) that comprises epoxy resin, solidifying agent, curing catalyst and the coupling agent etc. that contain fluorene skeleton.The wet fastness of the cured article of the composition of the epoxy resin that contains fluorene skeleton is high, can effectively suppress the deteriorated of organic EL.But, when the sealing of element, must, by said composition heating and melting, then carry out injection moulding.Therefore, there is the problem of sealing process complexity.
On the other hand, the sheet for sealing (for example, with reference to patent documentation 2 and patent documentation 3) by the composition acquisition that contains low-molecular-weight epoxy resin, high molecular expoxy resin, potentiality imidazolium compounds and silane coupling agent is also proposed.These sheet for sealing can only carry out transfer printing by composition epoxy resin hot pressing is connected to element, and epoxy resin are heating and curing and by element sealing (face seal).
Prior art document
Patent documentation
Patent documentation 1: TOHKEMY 2005-41925 communique
Patent documentation 2: TOHKEMY 2006-179318 communique
Patent documentation 3: TOHKEMY 2007-112956 communique
Summary of the invention
Invent problem to be solved
But, the existing sheet for sealing of recording in patent documentation 2 and patent documentation 3 etc. is very soft if the temperature rise of sheet for sealing can become.Therefore,, when by element and sheet for sealing laminating, have and easily enter air, and the air entering becomes the situation of bubble.In addition, because sheet for sealing is soft, therefore, when the vacuum technology of utilizing vacuum laminator etc. is fitted, the air entering during laminating easily condenses.If there is bubble between element and sheet for sealing, the transparency of this part can reduce, and the efficiency of taking out light from optical element can reduce.In addition, if there is large bubble at the interface of element and sheet for sealing, the adaptation of element and sheet for sealing can reduce, at the interface of element and sheet for sealing, can peel off, thus element deteriorated (generation of dim spot).
The present invention proposes in view of such situation, and object is to provide a kind of flaky resin composition, and its air when thermo-compressed is difficult for entering to the particularly middle body of sheet, and the transparency of cured article is high, so with the adaptation excellence of optical element etc.
For solving the method for problem
The discoveries such as the inventor, by making the storage elastic modulus of 50 ℃ of sheet composition epoxy resin and the storage elastic modulus of 80 ℃ meet specific relation, thereby when the thermo-compressed of sheet composition epoxy resin, can prevent that air from entering between sheet composition epoxy resin and element etc.And find, by the storage elastic modulus of 80 ℃ of sheet composition epoxy resin is set as to specific scope, even thereby in sheet composition epoxy resin, produce bubble, also can suppress the cohesion of bubble, the transparency that can suppress the interface of sheet and element reduces, interface peel.
[1] a sheet composition epoxy resin, it comprises (A) weight-average molecular weight is 2 × 10
3～1 × 10
5epoxy resin and (B) curing catalyst; The storage elastic modulus G ' (50) of 50 ℃ and the storage elastic modulus G ' (80) of 80 ℃ meet the relation of G ' (50)/G ' (80) < 11, and G ' (80) is 2500Pa～5 × 10
5pa.
[2] the sheet composition epoxy resin as described in [1], the fusing point of above-mentioned (B) curing catalyst is below 50 ℃.
[3] the sheet composition epoxy resin as described in [1] or [2], further comprises the epoxy resin that (C) weight-average molecular weight is 100～1200.
[4] the sheet composition epoxy resin as described in [3], with respect to total 100 mass parts of above-mentioned (A) composition and above-mentioned (C) composition, the amount of above-mentioned (B) composition is 0.1 mass parts～10 mass parts.
[5] the sheet composition epoxy resin as described in [3] or [4], the epoxy equivalent (weight) of above-mentioned (C) composition is 80g/eq～300g/eq.
[6] the sheet composition epoxy resin as described in any one in [3] to [5], further comprise (D) have epoxy group(ing) or can with the silane coupling agent of the functional group of epoxy reaction, with respect to above-mentioned (B) composition, (C) composition and (D) total 100 mass parts of composition, above-mentioned (A) composition that contains 100 mass parts～2000 mass parts.
[7] the sheet composition epoxy resin as described in any one in [1] to [6], the weight-average molecular weight of above-mentioned (A) composition is 3 × 10
3～8 × 10
4.
[8] the sheet composition epoxy resin as described in any one in [1] to [7], the epoxy resin of above-mentioned (A) composition is the oligopolymer that comprises the repeated structural unit shown in following general formula (1):
[in general formula (1),
X represent singly-bound, methylene radical, isopropylidene ,-S-or-SO
2-,
R
1represent that independently of one another carbonatoms is 1～5 alkyl,
N represents more than 2 repeat numbers,
P represents 0～4 integer].
[9] the sheet composition epoxy resin as described in [8], the oligopolymer of the epoxy resin of above-mentioned (A) composition comprises in a part: the Bisphenol F type repeated structural unit that the X in above-mentioned general formula (1) is methylene radical, and the bisphenol A-type repeated structural unit that is isopropylidene of the X in above-mentioned general formula (1), the number (F) of contained Bisphenol F type repeated structural unit ading up to more than 50% with respect to the number (A) of above-mentioned bisphenol A-type repeated structural unit contained in above-mentioned oligopolymer a part and number (F) of above-mentioned Bisphenol F type repeated structural unit in above-mentioned oligopolymer a part.
[10] a kind of manufacture method of sheet composition epoxy resin, it is for manufacturing the method for the sheet composition epoxy resin described in any one in above-mentioned [1] to [9], and it comprises following operation: the operation of the composition that coating contains above-mentioned (A) composition and above-mentioned (B) composition on base material; And make the dry operation of above-mentioned composition.
[11] sheet for sealing, it comprises the layer that contains the sheet composition epoxy resin as described in any one in above-mentioned [1] to [9].
[12] sheet for sealing as described in [11], has protective membrane at least one mask of the layer that comprises above-mentioned sheet composition epoxy resin.
[13] sheet for sealing as described in above-mentioned [11] or [12], it is for by organic EL face seal.
[14] sheet for sealing as described in any one in above-mentioned [11] to [13], moisture component is below 0.1 quality %.
[15] a kind of organic EL panel, it comprises: display base plate, and the counter substrate of above-mentioned display base plate pairing, be disposed at organic EL on above-mentioned display base plate and between above-mentioned display base plate and above-mentioned counter substrate and by the containment member of above-mentioned organic EL sealing, above-mentioned containment member is the cured article of the sheet composition epoxy resin as described in any one as middle in above-mentioned [1] to [9].
[16] manufacture method for organic EL panel, it comprises following operation: the operation that the sheet composition epoxy resin hot pressing as described in any one in above-mentioned [1] to [9] is connected to organic EL; And make the curing operation of above-mentioned sheet composition epoxy resin after above-mentioned thermo-compressed.
[17] manufacture method of the organic EL panel as described in [16], is characterized in that, the hot pressing of above-mentioned sheet composition epoxy resin is connected to the above-mentioned organic EL that is heated to 50 ℃～110 ℃.
[18] OLED display, it possesses above-mentioned [15] described organic EL panel.
[19] organic EL illuminating, it possesses above-mentioned [15] described organic EL panel.
The effect of invention
According to the present invention, when the thermo-compressed of element etc. and sheet composition epoxy resin, air is difficult to enter their interface.In addition, even if air enters a little or the inner bubble that produces, these bubbles are also difficult for cohesion.
Accompanying drawing explanation
Fig. 1 is the sectional view that represents an example of sheet for sealing of the present invention.
Fig. 2 is the sectional view that represents an example of organic EL panel of the present invention.
Fig. 3 is the storage elastic modulus G ' (50) of 50 ℃ and ratio G ' (the 50)/G ' (80) of storage elastic modulus G ' (80) of 80 ℃ and the chart of the relation of G ' (80) that represents the sheet composition epoxy resin of embodiments of the invention and comparative example.
Embodiment
1. sheet composition epoxy resin
Sheet composition epoxy resin of the present invention at least comprises (A) high molecular expoxy resin and (B) curing catalyst.Sheet composition epoxy resin can comprise as required: (C) low-molecular-weight epoxy resin, (D) have epoxy group(ing) or can with the silane coupling agent of the functional group of epoxy reaction, (E) solvent and other compositions.In addition, sheet composition epoxy resin of the present invention is preferably thermoset.The curing catalyst of thermoset composition, compared with the curing catalyst of Photocurable composition, is difficult for while solidifying decomposing.In addition, the resolvent of heat cured curing catalyst is difficult for making optical element deteriorated, is also difficult for the transparency of the cured article of infringement composition.
About sheet composition epoxy resin of the present invention, the storage elastic modulus G ' (50) of 50 ℃ and the storage elastic modulus G ' (80) of 80 ℃ meet the relation of G ' (50)/G ' (80) < 11.Sheet composition epoxy resin more preferably meets G ' (50)/G ' (80) < 8, is further preferably and meets G ' (50)/G ' (80) < 5.
Conventionally, the thermo-compressed of sheet composition epoxy resin is carried out in the steps below.1) heat to 50 ℃～100 ℃ by thermo-compressed material on, thermo-compressed sheet composition epoxy resin.Then, 2) they are kept to certain hour at 80 ℃～100 ℃, make sheet composition epoxy resin completely curing.
In aforesaid method, 1), during thermo-compressed, sheet composition epoxy resin is contacted successively with by thermo-compressed material from end side.Therefore, the temperature rising of sheet composition epoxy resin.Conventionally, the temperature of the sheet composition epoxy resin at thermo-compressed initial stage is 50 ℃ of left and right, and the temperature of sheet composition epoxy resin when thermo-compressed finishes is 80 ℃ of left and right.1), in thermo-compressed, if the storage elastic modulus of sheet composition epoxy resin significantly reduces, sheet composition epoxy resin can become soft.And air easily enters to by between thermo-compressed material and sheet composition epoxy resin.
On the other hand, in the present invention, during thermo-compressed sheet composition epoxy resin, thermo-compressed starts (50 ℃) to thermo-compressed and finishes (80 ℃), the storage elastic modulus of sheet composition epoxy resin is difficult for changing.Therefore, air be difficult to enter to sheet composition epoxy resin with by the interface of thermo-compressed material, sheet composition epoxy resin with by the interface of thermo-compressed material, be difficult to produce bubble.
The example that reduces the method for the value of G ' (50)/G ' (80) has: improve the method that contain ratio (quality %) of (A) high molecular expoxy resin with respect to whole compositions of sheet composition epoxy resin; Improve the method that contains ratio of high-viscosity epoxy resin etc.(A) high molecular expoxy resin is compared with low-molecular-weight resin composition, and the temperature dependency of storage elastic modulus is few.Therefore,, if (A) high molecular expoxy resin improves with respect to the ratio that contains of whole compositions of composition epoxy resin, the value of G ' (50)/G ' (80) diminishes.
Herein, the storage elastic modulus G ' (80) of 80 of sheet composition epoxy resin of the present invention ℃ is 2500Pa～5 × 10
5pa, is preferably 5 × 10
3pa～2 × 10
5pa.If contain low molecular weight compositions, solvent in sheet composition epoxy resin, heating while also having low molecular weight compositions, solvent due to thermo-compressed volatilized, and produces the situation of bubble in sheet composition epoxy resin.But in the present invention, the storage elastic modulus G ' (80) during due to higher temperatures (80 ℃) is that 2500Pa is above, higher, the bubble that therefore produced is difficult to mobile in composition, and bubble is difficult for cohesion.Consequently at sheet composition epoxy resin and between by thermo-compressed material, the transparency is difficult reduces.In addition, sheet composition epoxy resin with by the adaptation at the interface of thermo-compressed material, also become good.And on the other hand, because the storage elastic modulus G ' (80) of 80 ℃ is 5 × 10
5below Pa, therefore flaky resin composition can be fully softening during thermo-compressed, flaky resin composition with can be fully closely sealed by thermo-compressed material.
The example that improves the method for the storage elastic modulus G ' (80) of 80 ℃ has: improve the method that contain ratio (quality %) of the little resin-phase of epoxy equivalent (weight) for whole compositions of sheet composition epoxy resin.If improve the ratio that contains of the little resin of epoxy equivalent (weight), the cross-linking density in sheet composition epoxy resin can improve, and the storage elastic modulus of 80 ℃ can improve.
Storage elastic modulus G ' (50) and G ' (80) are to pass through rheometer, measuring frequency: 1Hz, heat-up rate: 4 ℃/min, measure temperature range: 40 ℃～150 ℃, to the sheet composition epoxy resin of thickness 250 μ m～300 μ m measure and value.The example of rheometer has the rheometer (RS150 type) of Haake company system etc.
(A) high molecular expoxy resin
So-called in the present invention (A) high molecular expoxy resin is that weight-average molecular weight is 2 × 10
3～1 × 10
5epoxy resin, weight-average molecular weight is preferably 3 × 10
3～8 × 10
4, more preferably 4 × 10
3～6 × 10
4.Above-mentioned weight-average molecular weight is measured under the following conditions by the gel permeation chromatography using polystyrene as reference material (GPC).
Device: SHODEX system, GPC-101
Developing solvent: tetrahydrofuran (THF)
Polystyrene standard: VARIAN PS-1(molecular weight 580～7,500,000 processed), VARIAN PS-2(molecular weight 580～377,400 processed)
The viscosity of the epoxy resin that conventionally, weight-average molecular weight is above-mentioned scope is high.Therefore,, if contain (A) high molecular expoxy resin in sheet composition epoxy resin, the shape stability of sheet can improve.The temperature dependency of the storage elastic modulus of (A) high molecular expoxy resin is lower in addition.Therefore,, if contain (A) high molecular expoxy resin more than specified quantitative in sheet composition epoxy resin, aforesaid G ' (50)/G ' (80) becomes desired scope.
If consider the cross-linking density of sheet composition epoxy resin etc., the epoxy equivalent (weight) of (A) high molecular expoxy resin is preferably 500g/eq～1 × 10
4g/eq, more preferably 600g/eq～9000g/eq.
With regard to the viewpoint of the Water Vapour Permeability step-down of sheet, (A) high molecular expoxy resin is preferably the resin of main chain containing bis-phenol skeleton.Be particularly preferably and contain bis-phenol and the Epicholorohydrin resin as monomer component, more preferably its oligopolymer.
The monomer component that forms (A) high molecular expoxy resin can be all bis-phenol and Epicholorohydrin; But a part that forms the monomer component of epoxy resin also can be the composition (comonomer composition) beyond bis-phenol or Epicholorohydrin.The example of above-mentioned comonomer composition comprises 2 yuan of above polyvalent alcohols (for example phenol of 2 yuan, glycol etc.).If a part for monomer component is the composition (comonomer composition) beyond bis-phenol or Epicholorohydrin, molecular weight easily becomes desired scope.
(A) preference of high molecular expoxy resin comprises the resin with the repeated structural unit shown in following general formula (1).
In general formula (1), X represent singly-bound, methylene radical, isopropylidene ,-S-or-SO
2-.In general formula (1), the structural unit that X is methylene radical is Bisphenol F type structural unit; X is that the structural unit of isopropylidene is bisphenol A-type structural unit.N is the repeat number of the structural unit shown in general formula (1), is more than 2 integers.
In general formula (1), P is the replacement number of substituent R 1, is 0～4 integer.With regard to the viewpoint of thermotolerance, low-moisture permeability, P is preferably 0.R
1the alkyl that is 1～5 for carbonatoms independently of one another, is preferably methyl.
In oligopolymer as (A) high molecular expoxy resin, " the bisphenol A-type repeated structural unit " these two kinds that the X in " Bisphenol F type repeated structural unit " and above-mentioned general formula (1) that to be preferably the X that contains in above-mentioned general formula (1) be methylene radical is isopropylidene.If contain bisphenol A-type repeated structural unit in oligopolymer, the viscosity of sheet composition epoxy resin can improve.On the other hand, if contain Bisphenol F type repeated structural unit in oligopolymer, the sterically hindered of oligopolymer diminishes.Therefore, multiple phenylenes are easily orientated, the Water Vapour Permeability step-down of the cured article of sheet composition epoxy resin.
In above-mentioned oligopolymer a part, the number (F) of contained " Bisphenol F type repeated structural unit " is with respect to the total ratio ((F/(A+F)) × 100 of the number (A) of " bisphenol A-type repeated structural unit " contained in above-mentioned oligopolymer a part and the number (F) of " Bisphenol F type repeated structural unit ") be preferably more than 50%, more preferably more than 55%.If contain a large amount of " Bisphenol F type repeated structural unit ", the Water Vapour Permeability of the cured article of sheet composition epoxy resin can abundant step-down.
With respect to aftermentioned (B) curing catalyst, (C) low-molecular-weight epoxy resin and (D) total 100 mass parts of silane coupling agent, (A) content of high molecular expoxy resin is preferably 100 mass parts～2000 mass parts, more preferably 210 mass parts～2000 mass parts, more preferably 250 mass parts～1200 mass parts.If (A) ratio that contains of high molecular expoxy resin is above-mentioned scope, aforesaid G ' (50)/G ' (80) becomes desired scope.In addition, if (A) high molecular expoxy resin to contain ratio too high, the mobility step-down of composition when hot pressing is connected to by thermo-compressed material.Therefore, between by thermo-compressed material and sheet composition epoxy resin, easily produce gap.On the other hand, if (A) high molecular expoxy resin to contain ratio too low, the shape-holding property step-down of sheet composition epoxy resin, also step-down of the wet fastness of cured article.
While containing (C) described later low-molecular-weight epoxy resin in sheet composition epoxy resin, with respect to (C) low-molecular-weight epoxy resin 100 mass parts, (A) content of high molecular expoxy resin is preferably 100 mass parts～1500 mass parts, more preferably 120 mass parts～1200 mass parts.If (A) the above-mentioned ratio that contains of high molecular expoxy resin is below 1500 mass parts, the mobility of the composition while the hot pressing of sheet composition epoxy resin being connected to by thermo-compressed material easily improves.On the other hand, if (A) the above-mentioned ratio that contains of high molecular expoxy resin is more than 100 mass parts, the shape stability of sheet composition epoxy resin easily improves.In addition, also further abundant step-down of the Water Vapour Permeability of cured article.
(B) curing catalyst
The contained curing catalyst of sheet composition epoxy resin of the present invention, has and makes the curing beginning of epoxy resin and promote curing function.The example of curing catalyst comprises: imidazolium compounds, amine compound.The example of imidazolium compounds comprises: 1,2 dimethylimidazole, 2-ethyl-4-methylimidazole etc.; The example of amine compound comprises three-dimethylaminomethyl phenol etc.(B) curing catalyst also can be lewis base compound.Curing catalyst is preferably heat cured curing catalyst.Heat cured curing catalyst is difficult to make optical element etc. deteriorated.And then, when curing, be difficult to produce the transparent resolvent of cured article that may damage composition.
(B) to be preferably fusing point be below 50 ℃ to curing catalyst.If (B) curing catalyst is solid state when thermo-compressed, in sheet composition epoxy resin, can disperse fully, and easily produce curing inhomogeneous.And, have and in the cured article of sheet composition epoxy resin, produce bonding inhomogeneous, transparent situation about reducing.In addition, when the thermo-compressed of sheet composition epoxy resin, if (B) curing catalyst is solid state, (B) curing catalyst of solid state becomes core and bubble easily condenses.On the other hand, if (B) curing catalyst is liquid, the transparency of the cured article of sheet composition epoxy resin is difficult to reduce.In addition, if (B) curing catalyst is liquid, in sheet composition epoxy resin, easily disperse, solidified nature improves.
(B) fusing point of curing catalyst is more preferably below 50 ℃, more preferably below 45 ℃.Fusing point is that the example of 50 ℃ of following (B) curing catalysts has: 1,2 dimethylimidazole, three-dimethylaminomethyl phenol, 2-ethyl-4-methylimidazole etc.
(B) molecular weight of curing catalyst is preferably 80～800, and more preferably 100～500, more preferably 120～250.If (B) molecular weight of curing catalyst is less than 80, there is volatility to uprise, when by sheet composition epoxy resin thermo-compressed, in sheet composition epoxy resin, produce the possibility of bubble.On the other hand, if molecular weight exceedes 800, the possibility that has the mobility of the sheet composition epoxy resin while making sheet composition epoxy resin thermo-compressed to reduce, and then the reduction of the diffustivity of the curing catalyst in sheet composition epoxy resin, be difficult to obtain sufficient solidified nature.
With respect to total 100 mass parts of (A) high molecular expoxy resin and (C) described later low-molecular-weight epoxy resin, (B) content of curing catalyst is preferably 0.1 mass parts～10 mass parts, more preferably 0.3 mass parts～8 mass parts, more preferably 0.5 mass parts～6 mass parts.If (B) the above-mentioned content of curing catalyst is below 10 mass parts, the stability in storage of sheet composition epoxy resin can improve.In addition, if (B) the above-mentioned content of curing catalyst is more than 0.3 mass parts, the solidified nature of sheet composition epoxy resin can improve.
(C) low-molecular-weight epoxy resin
In sheet composition epoxy resin, preferably contain (C) low-molecular-weight epoxy resin.(C) low-molecular-weight epoxy resin is that weight-average molecular weight is 100～1200 epoxy resin, and weight-average molecular weight is preferably 200～1100.Weight-average molecular weight and aforementionedly similarly measure.If (C) that weight-average molecular weight is above-mentioned scope, the mobility of sheet composition epoxy resin during sheet composition epoxy resin thermo-compressed can improve fully, and sheet composition epoxy resin is for being improved fully by the adaptation of thermo-compressed material.
(C) epoxy equivalent (weight) of low-molecular-weight epoxy resin is preferably 80g/eq～300g/eq, more preferably 100g/eq～200g/eq.If contain epoxy equivalent (weight), be (C) low-molecular-weight epoxy resin in above-mentioned scope, the hydrogen bond quantitative change in sheet composition epoxy resin is many, and the storage elastic modulus G ' (80) of 80 ℃ becomes desired scope.
(C) low-molecular-weight epoxy resin is preferably phenol-type epoxy resin, more preferably 2 yuan of above phenol type epoxy compoundss or comprise amphyl with Epicholorohydrin the oligopolymer as monomer component.
The example of 2 yuan of above phenol type epoxy compoundss comprises: bisphenol type epoxy compounds, phenol phenolic varnish type epoxy compounds, cresols phenolic varnish type epoxy compounds etc.The example of bisphenol type epoxy compounds comprises the compound shown in general formula (2).X, R in following general formula (2)
1and P can with general formula (1) in X, R
1and P is same.
Contain amphyl with Epicholorohydrin as the amphyl of the oligopolymer of monomer component example comprise: bis-phenol, A Hydrogenated Bisphenol A, phenol phenolic varnish, cresols phenolic varnish etc.
(C) preference of low-molecular-weight epoxy resin comprises: bisphenol type epoxy compounds or the oligopolymer using bis-phenol and Epicholorohydrin as monomer component.(C) the low-molecular-weight epoxy resin oligopolymer that more preferably the repeat number n in above-mentioned general formula (1) is 2～4.The affinity of such oligopolymer and (A) high molecular expoxy resin is high.
In addition, the repeated structural unit that (C) the contained repeated structural unit of low-molecular-weight epoxy resin can be contained with (A) high molecular expoxy resin is identical, also can be different.
With respect to (A) high molecular expoxy resin, (B) curing catalyst and (D) total 100 mass parts of silane coupling agent, (C) content of low-molecular-weight epoxy resin is 1 mass parts～100 mass parts, is preferably 5 mass parts～50 mass parts.If (C) ratio that contains of low-molecular-weight epoxy resin is above-mentioned scope, the mobility of the composition during by sheet composition epoxy resin thermo-compressed can fully improve.And then sheet composition epoxy resin can fully solidify.
(D) have epoxy group(ing) or can with the silane coupling agent of the functional group of epoxy reaction
In sheet composition epoxy resin of the present invention, also can contain: the silane coupling agent or 2 1) with epoxy group(ing)) have can with the silane coupling agent of the functional group of epoxy reaction.Refer to epoxy group(ing) and carry out addition reaction etc. with epoxy reaction.For example, if organic EL sheet for sealing shape composition epoxy resin contains silane coupling agent, the adaptation of the substrate of sheet composition epoxy resin and organic EL can improve.
In addition, there is epoxy group(ing) or have can with the silane coupling agent of the functional group of epoxy reaction, react with the epoxy resin in sheet composition epoxy resin.Therefore, with regard to being difficult to the viewpoint of residual low molecular weight compositions in the cured article of sheet epoxy composite, also preferred.
1) silane coupling agent that has an epoxy group(ing) is the silane coupling agent that contains the epoxy group(ing) such as glycidyl, and its example comprises: γ-glycidoxypropyltrime,hoxysilane, β-(3,4-epoxycyclohexyl) ethyl trimethoxy silane etc.
2) can comprise with the functional group of epoxy reaction: the amino such as primary amino, secondary amino group, carboxyls etc., also comprise in addition: be converted into can with the group of the functional group of epoxy reaction (such as methacryloyl, isocyanate group etc.).There is such can comprising with the example of the silane coupling agent of the functional group of epoxy reaction: N-2-(amino-ethyl)-3-aminopropyl methyl dimethoxysilane, N-2-(amino-ethyl)-3-aminopropyl methyltrimethoxy silane, N-2-(amino-ethyl)-3-aminopropyl Union carbide A-162, 3-TSL 8330, APTES, 3-triethoxysilyl-N-(1, 3-dimethyl-butylidene) propyl group amine, N-phenyl-3-TSL 8330 or 3-(4-methylpiperazine base) propyl trimethoxy silicane, trimethoxysilyl phenylformic acid, γ-methacryloxypropyl trimethoxy silane, and γ-isocyanate group propyl-triethoxysilicane etc.
In addition, in sheet composition epoxy resin, also can contain in the lump other silane coupling agents with above-mentioned silane coupling agent.The example of other silane coupling agents comprises: vinyltriacetoxy silane, vinyltrimethoxy silane etc.These silane coupling agents can only contain a kind, also can contain two or more.
The molecular weight of silane coupling agent is preferably 80～800.If the molecular weight of silane coupling agent exceedes 800, the mobility while having sheet composition epoxy resin thermo-compressed is insufficient, the situation that adaptation reduces.
With respect to sheet composition epoxy resin 100 mass parts, the content of silane coupling agent is preferably 0.05 mass parts～30 mass parts, more preferably 0.1 mass parts～20 mass parts, more preferably 0.3 mass parts～10 mass parts.
(E) solvent
Sheet composition epoxy resin of the present invention can mix aforesaid (A)～(D) solvent of composition equably containing being useful on.Solvent has makes the function that particularly high molecular expoxy resin disperses or dissolves equably.Solvent can be various organic solvents.Its example comprises: the aromatic solvents such as toluene, dimethylbenzene; The ketone series solvents such as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK); Ether, dibutyl ether, tetrahydrofuran (THF), two
the ethers such as alkane, ethylene glycol monoalkyl ether, glycol dialkyl ether, propylene glycol dialkyl ether; The non-proton property polar solvents such as N-Methyl pyrrolidone, dimethyl-imidazolinone, dimethylformaldehyde; The ester such as ethyl acetate, butylacetate class etc.Particularly, with regard to easily dissolving the aspect of high molecular expoxy resin, be preferably the ketone series solvents such as methyl ethyl ketone (thering is the solvent of ketone group).
(F) other any compositions
Sheet composition epoxy resin of the present invention, in the scope of the effect that infringement is not invented significantly, can further contain the composition arbitrarily such as other resinous principles, weighting agent, properties-correcting agent, stablizer.The example of other resinous principles has: polymeric amide, polyamidoimide, polyurethane(s), polyhutadiene, sovprene, polyethers, polyester, styrene-butadiene-styrene block copolymer, petroleum resin, xylene resin, ketone resin, celluosic resin, fluorine are that oligopolymer, silicon are that oligopolymer, polythioether are oligopolymer etc.These can only contain a kind, also can contain multiple.
The example of weighting agent comprises: granulated glass sphere, styrenic particle, methacrylate ester polymer particle, ethylene-based polymer particle, acrylic polymer particle.Weighting agent can contain multiple.
The example of properties-correcting agent comprises: polymerization causes auxiliary agent, antiaging agent, flow agent, wettability modifying agent, tensio-active agent, softening agent etc.These are capable of being combined multiple and use.The example of stablizer comprises: UV light absorber, sanitas, antiseptic-germicide.Properties-correcting agent can contain multiple.
(solidified nature of sheet composition epoxy resin)
The curing speed of sheet composition epoxy resin of the present invention is preferably to a certain degree high-speed.Reason is to improve the operability when by thermo-compressed material adhesive.Can promptly solidify and for example refer to that (80 ℃～100 ℃) solidified in 120 minutes under heating condition.
Whether sheet composition epoxy resin solidifies, can be as judged: make sheet composition epoxy resin on hot-plate, solidify and touch to be confirmed whether gelation by finger.In addition, whether sheet composition epoxy resin is curing also can obtain according to the transformation efficiency of epoxy group(ing).The transformation efficiency of epoxy group(ing) can be obtained as follows: the IR spectrum of the sheet composition epoxy resin before measuring respectively curing reaction and after curing reaction, according to the decrement of the epoxy group(ing) of this IR spectrum, obtain.The solidified nature of sheet composition epoxy resin can be controlled by the amount of adjusting curing catalyst.
(manufacture method of sheet composition epoxy resin)
Sheet composition epoxy resin of the present invention only otherwise damage effect of the present invention, can pass through method manufacture arbitrarily.For example can obtain sheet composition epoxy resin by following operation: 1) prepare (A) composition～(E) operation of composition; 2) make that (A) composition～(D) composition is dissolved in (E) composition, 30 ℃ of operations of mixing below; 3) on base material by the operation of this mixture coating slabbing; 4) by the dry operation of mixture of coating slabbing.
2) in operation, can be disposable by (A) composition～(E) composition mixes, and also can dissolve in (E) composition and mix after (A) composition, add other compositions and mix.The example of blending means comprises: these one-tenth are distributed in flask and the method stirring, by three rollers, carry out mixing method etc.
2) in operation, the mixture of gained is preferably 0.01Pas～100Pas the viscosity of 25 ℃.If the viscosity of mixture is above-mentioned scope, 3) screening characteristics of the mixture in operation improves, and can easily be shaped to sheet.Above-mentioned viscosity is the value 25 ℃ of mensuration by E type viscometer (eastern machine industry RC-500 processed).The viscosity of mixture amount by (E) composition etc. is adjusted.
3) coating process in operation is not particularly limited, for example, can be the method for use screen painting, divider, various coating rolls etc.In addition, there is no particular restriction for the kind of base material, for example, can be known mold release film etc.In addition, the coating thickness of mixture can suitably be selected according to the thickness of target sheet composition epoxy resin, and the thickness that is for example set as dried sheet composition epoxy resin for example becomes 1 μ m～100 μ m.
In addition, 4) drying temperature and time of drying in operation are set as: contained (A) high molecular expoxy resin of above-mentioned sheet composition epoxy resin, (C) low-molecular-weight epoxy resin do not solidify, and can be dried to remove to (E) solvent and become temperature, the time below desired amount.Drying temperature is for example 20 ℃～70 ℃, and be for example about 10 minutes～3 hours time of drying.Particularly, be preferably film is dried after about 10 minutes with 30 ℃～60 ℃ under the non-active gas atmosphere such as nitrogen atmosphere, then carry out vacuum-drying about 2 hours.So, by further carrying out vacuum-drying, thereby can remove above-mentioned contained solvent, moisture with lower drying temperature.Drying means is not particularly limited, for example, have warm air drying, vacuum-drying etc.
2. sheet for sealing
Sheet for sealing of the present invention is the sheet that comprises above-mentioned sheet composition epoxy resin, for example, comprise: base material film, be formed at above-mentioned sheet composition epoxy resin on this base material film, be formed at the protective membrane on this sheet composition epoxy resin as required.
With regard to suppressing the aspect of the impact of moisture on sealed material, the water ratio of the layer that comprises sheet composition epoxy resin of the present invention is preferably below 0.1 quality %, more preferably below 0.06 quality %.Particularly organic EL because of moisture easily deteriorated.Therefore,, during by sheet for sealing sealing organic el element, preferably reduce as far as possible water ratio.For example can reduce by sheet for sealing being carried out to heat drying under vacuum etc. the water ratio of sheet for sealing.
The water ratio of sheet for sealing of the present invention for example can be obtained as follows: measure the coupons of above-mentioned of about 0.1g, by Ka Shi moisture meter, be heated to 150 ℃, measure the amount of moisture that now produced and obtain (solid evaporating method).
The thickness of the layer that comprises sheet composition epoxy resin of the present invention also depends on the kind of sealed material, for example, be 1 μ m～100 μ m, is preferably 10 μ m～30 μ m, more preferably 20 μ m～30 μ m.
The layer that comprises sheet composition epoxy resin of the present invention is preferably has appropriate mobility at thermo-compressed temperature.Reason is: such as, during sealing organic el element etc., utilize the sheet of fluidization by heating, successfully packing elements surface concavo-convex and get rid of gap.Mobility during thermo-compressed judges by fluxing point.Fluxing point is the temperature that is showed to mobility when heating layer that comprises above-mentioned sheet composition epoxy resin, is preferably 30 ℃～100 ℃.
Fluxing point is to load on the sheet glass of hot-plate, and (m), above-mentioned starts the temperature of melting to thickness 100 μ to press above-mentioned.
If fluxing point is less than 30 ℃, exist while carrying out hot transfer printing (thermo-compressed) or carry out thermofixation and while sealing, the mobility of the layer that comprises sheet composition epoxy resin excessive and easily produce sagging, thereby be difficult to the situation of the thickness of managing cured article.On the other hand, if fluxing point exceedes 100 ℃, operability variation during hot transfer printing.Therefore, between sheet for sealing and sealed material, easily form gap or by heating, sealed material (for example organic EL) caused to detrimentally affect.On the other hand, if fluxing point is 30 ℃～100 ℃, can be suppressed between the layer that comprises sheet composition epoxy resin and element and forms gap, and obtain good adaptation.
As mentioned above, sheet for sealing can comprise the layer that contains sheet composition epoxy resin of the present invention and base material film, protective membrane.The example of base material film, protective membrane comprises known mold release film, is preferably film having moisture barrier or barrier properties for gases etc., more preferably polyethylene terephthalate.The thickness of base material film or protective membrane also depends on membrane material, with regard to having for regard to the aspect of the tracing ability of the sealed materials such as organic EL etc., for example, is 50 μ m left and right.
Sheet for sealing of the present invention further air inclusion barrier layer as required.Gas-barrier layer can be the moisture that suppresses in extraneous gas etc., makes the layer in the deteriorated moisture of organic EL, gas permeation organic EL panel.Optional position beyond the configurable face in contacting with organic EL of such gas-barrier layer, is preferably between the layer that is disposed at base material film and comprise sheet composition epoxy resin of the present invention.
There is no particular restriction for the material of formation gas-barrier layer.The example that forms the material of gas-barrier layer comprises: Al, Cr, Ni, Cu, Zn, Si, Fe, Ti, Ag, Au, Co; The oxide compound of these metals; The nitride of these metals; The oxynitride of these metals etc.Gas-barrier layer can comprise a kind of metal, also can comprise two or more metal.In addition, gas-barrier layer also can comprise resin.
For example, for the gas-barrier layer of the diaphragm seal of the organic EL of sealed bottom illumination mode, be preferably the layer that luminous reflectance factor is high, for example, be preferably the layer that comprises Al, Cu etc.On the other hand, for sealing the gas-barrier layer of diaphragm seal of organic EL of top illumination mode, be preferably the layer that transmittance is high, for example, can be the layer that comprises polyethylene terephthalate (PET), polycarbonate (PC) etc.The thickness of gas-barrier layer can be 100 μ m～3000 μ m left and right.
The sheet for sealing with gas-barrier layer can form after gas-barrier layer on base material film, form comprise sheet composition epoxy resin of the present invention layer and manufacture.There is no particular restriction for the formation method of gas-barrier layer, as dry process, comprising: the CVD methods such as the various PVD methods such as vacuum evaporation, sputter, ion plating and plasma CVD; As wet process, comprising: plating method, coating method etc.
Be preferably further lamination protective membrane on the layer that comprises above-mentioned sheet composition epoxy resin.Lamination is for example preferably and uses laminating machine to carry out 60 ℃ of left and right.The thickness of protective membrane is for example 20 μ m left and right.
Fig. 1 is the preferably figure of an example that represents the formation of sheet for sealing.As shown in Figure 1, sheet for sealing 10 has: base material film 12, the protective membrane 18 that is formed at the layer 16 that comprises sheet composition epoxy resin on this base material film 12 and configures on the layer 16 that comprises sheet composition epoxy resin.
After such sheet for sealing 10 for example can be peeled off protective membrane 18, the layer 16 that comprises sheet composition epoxy resin exposing is configured and used in the mode contacting with the display base plate that disposes organic EL.
Sheet for sealing of the present invention for water ratio is maintained certain below, be preferably together with the siccative such as silica gel and preserve.
3. the purposes of sheet for sealing
Sheet for sealing of the present invention is used as containment member by being cured.The object of sealing is not particularly limited, for example, be preferably electro-optical device.The example of electro-optical device comprises: possess OLED display, organic EL illuminating, liquid-crystal display, LED of organic EL panel etc.
Sheet for sealing of the present invention is particularly preferably the containment member as organic EL panel.With regard to the viewpoint of the taking-up property of the light from organic EL panel, for sealing member, require the transparency.In addition, organic illuminating element because of moisture easily deteriorated, therefore low for sealing member special requirement Water Vapour Permeability.The layer that comprises sheet composition epoxy resin of the present invention is when by sheet for sealing thermo-compressed, and the situation that air enters is few, and then the situation of bubble cohesion is also few.Therefore, the transparency excellence after thermofixation, so that also excellent with adaptation and the low-moisture permeability of organic EL.Therefore, effective especially as the containment member of organic EL panel.Sheet composition epoxy resin of the present invention can preferably provide in organic EL panel the particularly containment member of the organic EL panel of top lighting structure.
The Water Vapour Permeability of the cured article of sheet composition epoxy resin of the present invention is preferably 60(g/m
224h), more preferably 30(g/m
224h).Water Vapour Permeability can be obtained by the cured article of measuring the sheet composition epoxy resin of 100 μ m according to JIS Z0208 under 60 ℃, 90%RH condition.
In addition, more than the cured article of sheet composition epoxy resin of the present invention and the bonding force of sealed material are preferably 300gf/15mm.
The bonding force of cured article and sealed material can be measured by the following method.
In the aluminium foil side that is fitted with the film of aluminium foil and PET (goods name: Alpet), (thickness is about 15 μ m) and is dry and form coating sheet composition epoxy resin.Then, by the surface of sheet composition epoxy resin on glass substrate (JIS R3202 reference glass, 100mm × 25mm × 2mm), use roll laminating machine (MCK company system, MRK-650Y type), with speed 0.3m/min, carry out thermo-compressed under the conditions of heating up and down 90 ℃ of cylinder moulding pressure 0.2MPa, roll temperature.This multilayer body is heated 30 minutes at 80 ℃ by baking oven, sheet composition epoxy resin is solidified.Then, multilayer body is cut into width 15mm, by electronic stripping tester (device name: STOROGRAPH E-S, scope (range) 50mm/min), measure 90 degree stripping strengths of glass substrate and sheet composition epoxy resin.In the present invention, this 90 degree stripping strength is made as above-mentioned bonding force.
In addition, the Tg of the cured article of sheet composition epoxy resin of the present invention is preferably more than 80 ℃.The Tg of cured article is the TMA/SS6000 that uses TMA(Seiko electronics corporation system), with the condition of 5 ℃/min of heat-up rates, measure linear expansivity, according to its flex point, obtain.
In addition, the solvent phase of sheet composition epoxy resin of the present invention is below 50000 quality ppm for the content of the whole compositions of resin combination, is preferably below 30000 quality ppm.If the solvent in flaky resin composition is many, the possibility that has solvent to impact sealed material.Quantity of solvent in flaky resin composition is for example used IR absorption spectrometry device (the Japanese light splitting FT/IR-4100 processed of company) to measure.To comprise methyl ethyl ketone (MEK) as the situation of solvent as example, the measuring method of quantity of solvent is described.
Prepare in advance by GC/MS Analysis method (GC-MS) quantity of solvent has been carried out to quantitative standard model (sheet composition epoxy resin), and this standard model is carried out to IR absorption spectrometry.The IR absorption spectrum of according to standard sample, calculates C=O absorption peak (the about 1710cm of MEK
-1) with respect to C=C absorption peak (the about 1609cm of epoxy resin
-1) strength ratio.Then, working sample (sheet composition epoxy resin) is carried out to IR absorption spectrometry, calculate C=O absorption peak (the about 1710cm of MEK
-1) with respect to C=C absorption peak (the about 1609cm of epoxy resin
-1) strength ratio.Obtain the peak intensity of working sample than the ratio of the peak intensity ratio with respect to standard model, calculate quantity of solvent contained in working sample.
Organic EL panel has: the substrate (display base plate) that disposes organic EL; Counter substrate with display base plate pairing; Between display base plate and counter substrate, and by the containment member of above-mentioned organic EL sealing.As previously mentioned, containment member is filled in to the space being formed between organic EL and counter substrate, the organic EL panel of gained is called to face seal type organic EL panel.Sheet composition epoxy resin of the present invention is particularly suitable for the face seal type containment member of the organic EL panel of making top lighting structure.
Fig. 2 is the sectional view that schematically shows the face seal type organic EL panel of top lighting structure.As shown in Figure 2, organic EL panel 20 successively lamination has: display base plate 22, organic EL 24 and counter substrate (transparency carrier) 26, around organic EL 24 and between counter substrate (transparency carrier) 26, filling containment member 28.In organic EL panel of the present invention, the containment member 28 in Fig. 2 is the cured article of aforesaid sheet composition epoxy resin of the present invention.
Organic EL panel using the cured article of sheet composition epoxy resin of the present invention as containment member can be manufactured by method arbitrarily.For example, above-mentioned organic EL panel 20 can be by being connected to sheet composition epoxy resin of the present invention hot pressing after display base plate, makes after thermo-compressed above-mentioned to solidify and manufacture.
Particularly, through following operation, manufacture: the operation that 1) obtains the multilayer body that disposes the display base plate 22 of organic EL 24, sheet composition epoxy resin of the present invention and counter substrate (transparency carrier) 26; 2) make above-mentioned of multilayer body of gained carry out the operation of thermo-compressed; 3) make above-mentioned curing operation after thermo-compressed.Each operation is as long as according to known method.
1) in operation, also can be on the display base plate 22 that disposes organic EL 24, after mounting (or transfer printing) sheet composition epoxy resin, in mounting (or transfer printing), there is on the display base plate 22 of above-mentioned the counter substrate (transparency carrier) 26 of overlapping pairing and obtain multilayer body (method (i)).
Now, after the above-mentioned sheet composition epoxy resin of the side protective film of sheet composition epoxy resin with protective membrane can being peeled off and expose being loaded on organic EL, the opposing party's protective membrane is peeled off and carried out transfer printing; Also can the above-mentioned sheet composition epoxy resin without protective membrane directly be loaded on organic EL by roll laminating machine etc.
Or, can first prepare to be provided with in advance the member of the layer that comprises sheet composition epoxy resin of the present invention in counter substrate 26, it is fitted on the display base plate 22 that is formed with organic EL 24 and obtain multilayer body (method (ii)).The method is to for example not stripping the base material (or base material film) of sheet composition epoxy resin, and direct-assembling to the situation of organic EL panel is effective.
2), in operation, by using vacuum lamination machine to make above-mentioned for example 50 ℃～110 ℃ thermo-compressed, carry out organic EL and the thermo-compressed of above-mentioned and the thermo-compressed of display base plate 22 and counter substrate 26.Now, be preferably organic EL side is heated to 50 ℃～110 ℃ in advance, make organic EL and the laminating of sheet composition epoxy resin.
3) in operation, the solidification value of for example 80 ℃～100 ℃ make above-mentioned completely curing.Be heating and curing to be preferably the temperature of 80 ℃～100 ℃ and carry out about 0.1 hour～2 hours.In addition, to be made as 100 ℃ of following reasons be can not cause damage to organic EL to the temperature when being heating and curing.
Embodiment
Below, with reference to embodiment and comparative example and further illustrate the present invention.Technical scope of the present invention is not limited and is explained by these embodiment and comparative example.First, the each composition using in expression embodiment and comparative example.In addition, the weight-average molecular weight of composition (A) is designated as the measured value of measuring by aforesaid method.
(A) high molecular expoxy resin
< bisphenol A type epoxy resin >
JER1001(Mitsubishi Chemical Ind system): weight-average molecular weight 2322, epoxy equivalent (weight) 500g/eq
JER1010(Mitsubishi Chemical Ind system): weight-average molecular weight 38312, epoxy equivalent (weight) 5000g/eq
< bisphenol f type epoxy resin >
JER4004(Mitsubishi Chemical Ind system): weight-average molecular weight 5872, epoxy equivalent (weight) 880g/eq
JER4005(Mitsubishi Chemical Ind system): weight-average molecular weight 7582, epoxy equivalent (weight) 1070g/eq
JER4010(Mitsubishi Chemical Ind system): weight-average molecular weight 39102, epoxy equivalent (weight) 4400g/eq
< dihydroxyphenyl propane/bisphenol f type epoxy resin >
JER4275(Mitsubishi Chemical Ind system): weight-average molecular weight 58287, epoxy equivalent (weight) 9200g/eq, (number of the Bisphenol F type structural unit in a part): (number of the bisphenol A-type structural unit in a part)=75:25
< phenoxy group type epoxy resin >
JER1256(Mitsubishi Chemical Ind system): weight-average molecular weight 58688, epoxy equivalent (weight) 8500g/eq
Chemical company of YP-70(Nippon Steel system): weight-average molecular weight 60000, epoxy equivalent (weight) 12100g/eq
(B) curing catalyst
1,2-DMZ(1,2-methylimidazole, 37 ℃～39 ℃ of fusing points, molecular weight 96) (four countries change into company's system)
2PZ-CNS-PW(1-cyano ethyl-2-phenylimidazole
175 ℃～183 ℃ of trimellitate, fusing points) (four countries change into industrial's system)
2MAOK-PW(2,4-diamino-6-[2 '-Methylimidazole quinoline-(1 ')]-ethyl-s-triazine isocyanuric acid affixture (being 260 ℃ of solid, decomposition temperatures at 50 ℃) (four countries change into industrial's system)
SP170(Adeka Optomer SP-170(light cationic polymerization initiators)) (two (two (beta-hydroxy oxyethyl group) phenyl sulfonyl) aralkyl sulfid-bis--hexafluoro-antimonic acid esters of 4,4-, fusing point are below 25 ℃) (rising sun electrification company system)
(C) low-molecular-weight epoxy resin
< bisphenol A-type/bisphenol f type epoxy resin >
The large Japanese ink of EXA835-LV(chemical industrial company system): weight-average molecular weight 350, epoxy equivalent (weight) 170g/eq
< bisphenol f type epoxy resin >
YL983U(Mitsubishi Chemical Ind system): weight-average molecular weight 398, epoxy equivalent (weight) 170g/eq
JER807(Mitsubishi Chemical Ind system): weight-average molecular weight 229, epoxy equivalent (weight) 175g/eq
< phenol novolak type epoxy resin >
JER152(Mitsubishi Chemical Ind system): weight-average molecular weight 416, epoxy equivalent (weight) 178g/eq
JER154(Mitsubishi Chemical Ind system): weight-average molecular weight 1028, epoxy equivalent (weight) 180g/eq
(D) silane coupling agent
KBM-403(3-glycidoxypropyltrime,hoxysilane molecular weight 236) (chemical industrial company of SHIN-ETSU HANTOTAI system)
(E) solvent
MEK(methyl ethyl ketone)
[embodiment 1]
JER1001, the jER1010 of 0.3 mass parts and the jER154 of 0.35 mass parts that in flask, pack 0.35 mass parts into, add the methyl ethyl ketone of 2 mass parts, at room temperature stirring and dissolving therein.In this solution, add 1 of the KBM-403 of 0.04 mass parts and 0.06 mass parts, 2-DMZ, at room temperature stirs, and prepares the varnish of composition epoxy resin.
Use coating machine, with dry thickness, become the mode of approximately 20 μ m, by prepared varnish be coated on through the PET of demoulding processing film (the Purex A53 processed of film company of Di Ren Du Pont, 38 μ m) on, under vacuum, with 40 ℃, be dried 2 hours, at the lower sheet composition epoxy resin that obtains solid of room temperature (approximately 25 ℃).Then, on sheet composition epoxy resin, thermo-compressed is used as protective membrane through the PET of demoulding processing film (the Purex A31 processed of film company of Di Ren Du Pont), and obtains sheet for sealing.In addition, protective membrane is suitably peeled off, and makes sheet composition epoxy resin surface expose and use.
[embodiment 2～embodiment 9 and comparative example 1～comparative example 5]
Adopt composition ratio (mass ratio) as shown in table 1, in the mode identical with embodiment 1, prepare the varnish of composition epoxy resin, apply and be dried and obtain the sheet for sealing that is formed with sheet composition epoxy resin.
[evaluation]
To each sheet composition epoxy resin of embodiment 1～embodiment 9 and comparative example 1, comparative example 2, evaluate in accordance with the following methods Water Vapour Permeability, solidified nature, foaminess, the screening characteristics of sheet composition epoxy resin, the transparency of cured article, the storage period (pot life) of sheet epoxy composite, fluxing point, the storage elastic modulus G ' (50) of 50 ℃, the storage elastic modulus G ' (80) of 80 ℃ of bonding strength, cured article.The results are shown in table 1 and table 2.In addition, in the chart of Fig. 3, represent the storage elastic modulus G ' (50) of 50 ℃ of sheet composition epoxy resin of gained in embodiment 1～embodiment 9 and comparative example 1～comparative example 5 and ratio G ' (50)/G ' (80) of storage elastic modulus G ' (80) and the relation of G ' (80) of 80 ℃.
(1) bonding strength
By the PET film lamination of the aluminium foil of thickness 30 μ m and thickness 12 μ m and film (trade(brand)name Alpet; PANAC limited-liability company system) aluminium face on, use applicator apply aforesaid varnish.It is kept 10 minutes in rare gas element baking oven (30 ℃), then in vacuum drying oven (40 ℃), keep 2 hours, dry the removing of the MEK in varnish coated film obtained to the test film of the layer that is formed with sheet composition epoxy resin.
By the face of the sheet composition epoxy resin of this test film on the glass substrate of thickness 2mm by roll laminating machine (MCK company system, MRK-650Y type) carry out thermo-compressed (roll temperature: 90 ℃ up and down heating, cylinder pressure 0.2MPa, transfer rate 0.3m/min) after, in baking oven with 80 ℃ heating 30 minutes and make sheet composition epoxy resin solidify.
Then,, by cutter cuts test film portion, make the strip test film of width 15mm.By the 90 degree stripping strengths of electronic stripping tester (Japan Jing Ji manufacturing company system, device name: STOROGRAPH E-S, peeling rate 50mm/min) determination test sheet when glass substrate is peeled off.In addition, comparative example 3～comparative example 5 is evaluated.
(2) Water Vapour Permeability
M) upper at base material film (manufacture of film limited-liability company of A53(Di Ren Du Pont) thickness 38 μ, by applicator, apply aforesaid varnish.This film is kept 10 minutes in rare gas element baking oven (30 ℃).Then in vacuum drying oven (40 ℃), keep 2 hours, dry the removing of the MEK in varnish coated film obtained to the diaphragm seal of the layer that is formed with sheet composition epoxy resin.Sealing sheet is heated 30 minutes with 80 ℃ in baking oven, sheet composition epoxy resin is solidified.Then, base material film is peeled off and removed from the cured article of sheet composition epoxy resin, and the membranaceous cured article of acquisition sheet composition epoxy resin.In addition, the mode that becomes 25 μ m～30 μ m with the thickness of this membranaceous cured article applies.
In addition, the Water Vapour Permeability of membranaceous cured article is measured under 60 ℃ of temperature and humidity conditions, 90%RH according to JIS Z0208.Water Vapour Permeability is the thickness of the membranaceous cured article of instrumentation, with the form of the mean value of 3 samples, obtains the value that is converted into 100 μ m thickness.In addition, comparative example 3～comparative example 5 is not carried out to the evaluation of Water Vapour Permeability.
(3) solidified nature
By applicator, at base material film (manufacture of film limited-liability company of A53(Di Ren Du Pont) thickness 38 μ, m) go up and apply aforesaid varnish.This film is kept 10 minutes in rare gas element baking oven (30 ℃).Then, in vacuum drying oven (40 ℃), keep 2 hours, dry the removing of the MEK in varnish coated film obtained to the diaphragm seal of the layer that is formed with sheet composition epoxy resin.Then, the layer hot pressing of sheet composition epoxy resin is connected to the NaCl plate that is heated to 45 ℃ of left and right on hot-plate, and is cooled to after room temperature, base material film is peeled off, and be transferred on NaCl plate.Above after transfer printing, cover other NaCl plate, as IR absorption spectrometry sample.Now, the aluminium foil of used thickness 11 μ m is as the spacer between 2 NaCl plates.
Use the Japanese light splitting FT/IR-4100 processed of company as IR absorption spectrometry device, the sheet composition epoxy resin of following one of four states is measured.
(i) the sheet composition epoxy resin after just having held with NaCl plate holder
In baking oven 80 ℃ of heating the sheet composition epoxy resins after 30 minutes
(iii) after (ii) finishing, follow in baking oven at 80 ℃ of sheet composition epoxy resins that heat after 30 minutes
(iv) after (iii) finishing, follow in baking oven at 150 ℃ of sheet composition epoxy resins that heat after 2 hours
According to the IR absorption spectrum of above-mentioned one of four states, calculate the solidified nature (curing degree) of sheet composition epoxy resin.When calculating, above-mentioned state is (i) made as to curing degree 0%, state is (iv) made as to curing degree 100%.
Be accompanied by the reaction that is heating and curing of epoxy resin, and butyl oxide link (oxolane ring) reduces.Therefore, calculate (i)～in (iv) by the characteristic absorption of phenyl ring (about 1609cm
-1) characteristic absorption that is made as the butyl oxide link of internal standard (is about 910cm
-1) specific tenacity.Then, calculate (i) to the variable quantity of specific tenacity (ii) with respect to (i) to the ratio of the variable quantity of specific tenacity (iv) and (i) to the variable quantity of specific tenacity (iii) with respect to the (i) ratio to the variable quantity of specific tenacity (iv), the curing degree using these values as state (ii) and (iii).In addition, the evaluation to comparative example 3～comparative example 5 not being cured property.
(4) foaminess
Slide glass (6cm × 6cm) is disposed on the hot-plate that is heated to 90 ℃.The protective membrane of the one side of above-mentioned sheet for sealing is peeled off, used roll banding, sheet composition epoxy resin is fitted in to slide glass successively from end side.Equally, make 3 slide glasss that sheet composition epoxy resin thermo-compressed is formed, in the vacuum drying oven of 90 ℃ ,-100kPa(gauge pressure) lower preservation 2 minutes.Foamed state after this preservation of glass substrate side visual observation.That obtains sheet composition epoxy resin peels off the ratio of area with respect to the area of slide glass.
Foaminess evaluation is good adaptation, above-mentioned ratio to be less than to 5% situation be made as zero, is more than 5% and 30% the situation of being less than is made as △ by above-mentioned ratio, by above-mentioned ratio be more than 30% situation be made as ×.
(5) screening characteristics
At base material film (manufacture of film limited-liability company of A53(Di Ren Du Pont) thickness 38 μ m) above, with dried thickness, become the mode of approximately 20 μ m, by applicator, apply aforesaid varnish.This film is kept 10 minutes in rare gas element baking oven (30 ℃).Then in vacuum drying oven (40 ℃), keep 2 hours, dry the removing of the MEK in varnish coated film formed to the layer that comprises sheet composition epoxy resin.
The sheet composition epoxy resin of visual observation gained, is made as zero by nonpitting situation, the situation that has depression is made as × (screening characteristics evaluation).
(6) transparency
At base material film (film limited-liability company of A53(Di Ren Du Pont system) thickness 38 μ m) above, with dried thickness, become the mode of approximately 20 μ m, by applicator, apply aforesaid varnish.This film is kept 10 minutes in rare gas element baking oven (30 ℃).Then in vacuum drying oven (40 ℃), keep 2 hours, dry the removing of the MEK in varnish coated film formed to the layer that comprises sheet composition epoxy resin.
By the face of this sheet composition epoxy resin on the glass substrate of thickness 2mm by roll laminating machine (MCK company system, MRK-650Y type) carry out thermo-compressed (roll temperature: 90 ℃ up and down heating, cylinder pressure 0.2MPa, transfer rate 0.3m/min).The multilayer body of the glass substrate of visual observation gained and sheet composition epoxy resin, will be made as zero without muddy situation in multilayer body, will in multilayer body, have muddy situation to be made as × (transparency is evaluated).
(7) storage period of sheet composition epoxy resin
With screening characteristics and the transparency evaluation similarly, on base material film, form sheet composition epoxy resin layer.The sheet of gained is preserved 10 hours at normal temperatures and pressures.Then, slide glass (6cm × 6cm) is disposed on the hot-plate that is heated to 60 ℃.This slide glass and above-mentioned sheet epoxy resin layer is stressed to fold, by roll banding, from the laminating of the end of sheet composition epoxy resin.
The situation that sheet composition epoxy resin can be transferred on glass substrate is made as zero, and situation that cannot transfer printing is made as ×.
(8) fluxing point
At base material film (manufacture of film limited-liability company of A53(Di Ren Du Pont) thickness 38 μ m) above, to be dried rear thickness, become the mode of approximately 15 μ m, by applicator, apply aforesaid varnish.This film is kept 10 minutes in rare gas element baking oven (30 ℃), then in vacuum drying oven (40 ℃), keep 2 hours, dry the removing of the MEK in varnish coated film obtained to the diaphragm seal of the layer that is formed with sheet composition epoxy resin.By the strip test film of the about 40mm of dried diaphragm seal cut-out length, the about 5mm of width, on hot-plate, on the sheet glass of Yu Jing heating, under the closely sealed state that has sheet composition epoxy resin, test film is peeled off lentamente to 180 degree directions.From 35 ℃ of the design temperatures of hot-plate, start this operation, 1 ℃ of the every raising of design temperature is just prepared strip test film and repeatable operation again, and the adhesion separability of sheet composition epoxy resin reaches maximum temperature and is made as fluxing point when peeling off.In addition, comparative example 3～comparative example 5 is not carried out the mensuration of fluxing point.
(9) storage elastic modulus
Sheet composition epoxy resin on diaphragm seal is passed through to thermo-compressed and lamination multilayer on 45 ℃ of hot-plates, be adjusted into thickness 250 μ m～300 μ m, use Haake company rheometer processed (RS150 type), measuring frequency 1Hz, 4 ℃/min of heat-up rates, measure 40 ℃～150 ℃ of temperature ranges and measure, obtain the value of the storage elastic modulus G ' (80) of the storage elastic modulus G ' (50) of 50 ℃ and 80 ℃.
[table 1]
[table 2]
The sheet composition epoxy resin of embodiment 1～embodiment 6 does not all produce foaming in above-mentioned foaminess test.In these examples, G ' (50)/G ' (80) is below 5.That is, can think that sheet can not be overbated when the laminating of sheet composition epoxy resin, the interface of sheet composition epoxy resin and slide glass does not enter air.In addition, further can think because the value of G ' (80) is more than 10000, quite high, even if therefore produce bubble in sheet composition epoxy resin, also almost do not condense.In addition, the bonding strength of embodiment 1～embodiment 6, solidified nature are also abundant.Particularly contain in the embodiment 2 of bisphenol A-type/bisphenol f type epoxy resin, Water Vapour Permeability is low.
On the other hand, although the value of the sheet composition epoxy resin G ' (80) of embodiment 7 is more than 2500, be below 10000.Therefore, can think that while adding thermo-compressed, the inner bubble producing slightly condenses, at peripheral part, produce foaming.
In addition, although sheet composition epoxy resin G ' (50)/G ' (80) of embodiment 9 is less than 11, be greater than 8, therefore, in the time of can thinking flaky resin composition thermo-compressed, between sheet composition epoxy resin and slide glass, entered a little air, peripheral part foaming.
In addition, in the sheet composition epoxy resin of embodiment 8, the value of G ' (80) is below 10000, G ' (50)/G ' (80) is greater than 8, therefore,, in the time of can thinking flaky resin composition thermo-compressed, between sheet composition epoxy resin and slide glass, entered a little air, and these bubble part cohesions, therefore partly produce foaming.
On the other hand, in comparative example 1, G ' (50)/G ' (80) significantly exceedes 11.Therefore, can think that flaky resin composition overbates when thermo-compressed, between sheet composition epoxy resin and slide glass, enter air, integral foam.
In addition, in comparative example 2～comparative example 5, the value of G ' (80) is below 2500, and G ' (50)/G ' (80) significantly exceedes 11.Therefore, can think during the hot pressing of flaky resin composition is connected to slide glass, when by flaky resin composition thermo-compressed, between sheet composition epoxy resin and slide glass, enter a large amount of air, and these bubble cohesions, therefore entirety produces foaming.
In addition, added in 25 ℃ of comparative examples 3 that are (B) curing catalyst of solid, the transparency of cured article is very low.(B) fusing point of curing catalyst is high, and the heat during not by thermo-compressed melts.Therefore infer the transparent step-down of cured article.
If for example comparative example 3 and comparative example 1 or comparative example 9 and comparative example 1, implying that the value of G ' (50)/G ' (80) reduces by increasing high molecular expoxy resin amount.In addition, if for example comparative example 9 and embodiment 1 are implying that it is large that the value of G ' (80) becomes by increasing epoxy equivalent (weight) circlet epoxy resins amount.
Industry utilizability
The sheet composition epoxy resin situation that air enters between sheet composition epoxy resin and element when thermo-compressed of the present invention is few, the transparency and the adaptation excellence to element of cured article.Therefore, can be preferably as the sealing material in other devices such as the liquid-crystal display take OLED display as representative.
Nomenclature
10: sheet for sealing
12: base material film
16: the layer that comprises sheet composition epoxy resin
18: protective membrane
20: organic EL panel
22: display base plate
24: organic EL
26: counter substrate (transparency carrier)
28: containment member
30: negative electrode reflection electrode layer
32: organic EL layer
34: anode transparent electrode layer
Claims (19)
1. a sheet composition epoxy resin, it comprises:
(A) weight-average molecular weight is 2 × 10
3～1 × 10
5epoxy resin; And
(B) curing catalyst,
The storage elastic modulus G ' (50) of 50 ℃ and the storage elastic modulus G ' (80) of 80 ℃ meet the relation of G ' (50)/G ' (80) < 11, and G ' (80) is 2500Pa～5 × 10
5pa.
2. sheet composition epoxy resin as claimed in claim 1, the fusing point of described (B) curing catalyst is below 50 ℃.
3. sheet composition epoxy resin as claimed in claim 1, further comprises the epoxy resin that (C) weight-average molecular weight is 100～1200.
4. sheet composition epoxy resin as claimed in claim 3, with respect to total 100 mass parts of described (A) composition and described (C) composition, the amount of described (B) composition is 0.1 mass parts～10 mass parts.
5. sheet composition epoxy resin as claimed in claim 3, the epoxy equivalent (weight) of described (C) composition is 80g/eq～300g/eq.
6. sheet composition epoxy resin as claimed in claim 3, further comprise (D) have epoxy group(ing) or can with the silane coupling agent of the functional group of epoxy reaction;
With respect to described (B) composition, (C) composition and (D) total 100 mass parts of composition, described (A) composition that contains 100 mass parts～2000 mass parts.
7. sheet composition epoxy resin as claimed in claim 1, the weight-average molecular weight of described (A) composition is 3 × 10
3～8 × 10
4.
8. sheet composition epoxy resin as claimed in claim 1, the epoxy resin of described (A) composition is the oligopolymer that comprises the repeated structural unit shown in following general formula (1):
In general formula (1),
X represent singly-bound, methylene radical, isopropylidene ,-S-or-SO
2-,
R
1represent that independently of one another carbonatoms is 1～5 alkyl,
N represents more than 2 repeat numbers,
P represents 0～4 integer.
9. sheet composition epoxy resin as claimed in claim 8, the oligopolymer of the epoxy resin of described (A) composition comprises in a part: the bisphenol A-type repeated structural unit that the X in the Bisphenol F type repeated structural unit that the X in described general formula (1) is methylene radical and described general formula (1) is isopropylidene;
In described oligopolymer a part, the number (F) of contained Bisphenol F type repeated structural unit is more than 50% with respect to the total ratio of the number (A) of described bisphenol A-type repeated structural unit contained in described oligopolymer a part and the number (F) of described Bisphenol F type repeated structural unit.
10. a manufacture method for sheet composition epoxy resin, it is for manufacturing the method for the sheet composition epoxy resin described in any one in claim 1 to 9, and it comprises following operation:
The operation of the composition that coating contains described (A) composition and described (B) composition on base material;
Make the operation of described composition dries.
11. 1 kinds of sheet for sealing, it comprises and contains the layer of sheet composition epoxy resin as claimed in any one of claims 1-9 wherein.
12. sheet for sealing as claimed in claim 11, have protective membrane at least one mask of the layer that comprises described sheet composition epoxy resin.
13. sheet for sealing as claimed in claim 11, it is for by organic EL face seal.
14. sheet for sealing as claimed in claim 11, moisture component is below 0.1 quality %.
15. 1 kinds of organic EL panels, it comprises:
Display base plate;
Counter substrate with described display base plate pairing;
Be disposed at the organic EL on described display base plate; And
Between described display base plate and described counter substrate and by the containment member of described organic EL sealing;
Described containment member is the cured article of sheet composition epoxy resin as claimed in any one of claims 1-9 wherein.
The manufacture method of 16. 1 kinds of organic EL panels, it comprises following operation:
Sheet composition epoxy resin hot pressing is as claimed in any one of claims 1-9 wherein connected to the operation of organic EL; And
Make the curing operation of described sheet composition epoxy resin after described thermo-compressed.
The manufacture method of 17. organic EL panels as claimed in claim 16, is characterized in that, the hot pressing of described sheet composition epoxy resin is connected to the described organic EL that is heated to 50 ℃～110 ℃.
18. 1 kinds of OLED display, it possesses the organic EL panel described in claim 15.
19. 1 kinds of organic EL illuminatings, it possesses the organic EL panel described in claim 15.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011180329 | 2011-08-22 | ||
| JP2011-180329 | 2011-08-22 | ||
| PCT/JP2012/005230 WO2013027389A1 (en) | 2011-08-22 | 2012-08-21 | Sheet-shaped epoxy resin composition, and sealing sheet containing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103732658A true CN103732658A (en) | 2014-04-16 |
Family
ID=47746153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280040160.8A Pending CN103732658A (en) | 2011-08-22 | 2012-08-21 | Sheet-shaped epoxy resin composition, and sealing sheet containing same |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPWO2013027389A1 (en) |
| KR (1) | KR20140048252A (en) |
| CN (1) | CN103732658A (en) |
| TW (1) | TW201311755A (en) |
| WO (1) | WO2013027389A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106465505A (en) * | 2014-05-23 | 2017-02-22 | 味之素株式会社 | Manufacturing method for sealed body |
| CN107409447A (en) * | 2015-03-20 | 2017-11-28 | 味之素株式会社 | The manufacture method of packaging body |
| CN112512791A (en) * | 2018-08-03 | 2021-03-16 | 三菱化学株式会社 | Laminate and method for producing epoxy resin sheet |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5697048B2 (en) * | 2012-06-15 | 2015-04-08 | 古河電気工業株式会社 | Resin composition for sealing organic electroluminescent element, sealing film for organic electroluminescent element, gas barrier film for organic electroluminescent element, and organic electroluminescent element using the same |
| JP2015096571A (en) * | 2013-11-15 | 2015-05-21 | 日東電工株式会社 | Photocurable resin composition and photocurable resin composition-made sheet obtained by using the same |
| JPWO2015087807A1 (en) * | 2013-12-11 | 2017-03-16 | 積水化学工業株式会社 | Curable resin composition for sealing organic electroluminescence display element, curable resin sheet for sealing organic electroluminescence display element, and organic electroluminescence display element |
| JP6495182B2 (en) * | 2013-12-24 | 2019-04-03 | 株式会社ブリヂストン | Adhesive sheet, method for producing the same, and laminate |
| JP2015137333A (en) * | 2014-01-23 | 2015-07-30 | 三井化学株式会社 | Sheet like encapsulation material and sheet for encapsulation containing the same |
| JP6582807B2 (en) * | 2015-09-25 | 2019-10-02 | 味の素株式会社 | Manufacturing method of resin sheet |
| JP6474432B2 (en) * | 2017-01-11 | 2019-02-27 | 日本化薬株式会社 | Energy ray curable resin composition and cured product thereof |
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| JP2005126658A (en) * | 2003-01-07 | 2005-05-19 | Sekisui Chem Co Ltd | Curable resin composition, adhesive epoxy resin paste, adhesive epoxy resin sheet, electroconductive connecting paste, electroconductive connecting sheet and electronic parts-connected body |
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-
2012
- 2012-08-21 CN CN201280040160.8A patent/CN103732658A/en active Pending
- 2012-08-21 WO PCT/JP2012/005230 patent/WO2013027389A1/en active Application Filing
- 2012-08-21 KR KR1020147003505A patent/KR20140048252A/en not_active Application Discontinuation
- 2012-08-21 JP JP2013529872A patent/JPWO2013027389A1/en not_active Withdrawn
- 2012-08-22 TW TW101130343A patent/TW201311755A/en unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2001098411A1 (en) * | 2000-06-21 | 2001-12-27 | Mitsui Chemicals Inc. | Sealing material for plastic liquid crystal display cells |
| JP2007254743A (en) * | 2002-06-17 | 2007-10-04 | Sekisui Chem Co Ltd | Adhesive for sealing organic electroluminescent device, adhesive tape for sealing organic electroluminescent device, double-coated adhesive tape for sealing organic electroluminescent device, sealing method for organic electroluminescent device and organic electroluminescent device |
| JP2005126658A (en) * | 2003-01-07 | 2005-05-19 | Sekisui Chem Co Ltd | Curable resin composition, adhesive epoxy resin paste, adhesive epoxy resin sheet, electroconductive connecting paste, electroconductive connecting sheet and electronic parts-connected body |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106465505A (en) * | 2014-05-23 | 2017-02-22 | 味之素株式会社 | Manufacturing method for sealed body |
| CN106465505B (en) * | 2014-05-23 | 2019-09-20 | 味之素株式会社 | The manufacturing method of seal |
| CN107409447A (en) * | 2015-03-20 | 2017-11-28 | 味之素株式会社 | The manufacture method of packaging body |
| CN112512791A (en) * | 2018-08-03 | 2021-03-16 | 三菱化学株式会社 | Laminate and method for producing epoxy resin sheet |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201311755A (en) | 2013-03-16 |
| WO2013027389A1 (en) | 2013-02-28 |
| KR20140048252A (en) | 2014-04-23 |
| JPWO2013027389A1 (en) | 2015-03-05 |
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Application publication date: 20140416 |