CN112673065A - Sealing material for image display device - Google Patents
Sealing material for image display device Download PDFInfo
- Publication number
- CN112673065A CN112673065A CN202080003491.9A CN202080003491A CN112673065A CN 112673065 A CN112673065 A CN 112673065A CN 202080003491 A CN202080003491 A CN 202080003491A CN 112673065 A CN112673065 A CN 112673065A
- Authority
- CN
- China
- Prior art keywords
- skeleton
- epoxy resin
- sealing
- bisphenol
- display device
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003566 sealing material Substances 0.000 title claims abstract description 43
- 239000003822 epoxy resin Substances 0.000 claims abstract description 92
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 92
- 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 abstract description 60
- 229920005989 resin Polymers 0.000 claims abstract description 51
- 239000011347 resin Substances 0.000 claims abstract description 51
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 40
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 33
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 68
- 239000004305 biphenyl Substances 0.000 claims description 36
- 235000010290 biphenyl Nutrition 0.000 claims description 34
- 238000007789 sealing Methods 0.000 description 109
- 150000001934 cyclohexanes Chemical class 0.000 description 28
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical group C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 23
- 230000004888 barrier function Effects 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 18
- 125000002091 cationic group Chemical group 0.000 description 17
- 239000000463 material Substances 0.000 description 16
- -1 3,5, 5-trimethyl-1, 1-cyclohexanediyl Chemical group 0.000 description 15
- 239000004593 Epoxy Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000000565 sealant Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000000203 mixture Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 230000035699 permeability Effects 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000013034 phenoxy resin Substances 0.000 description 6
- 229920006287 phenoxy resin Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 229920002799 BoPET Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000006059 cover glass Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 150000003077 polyols Chemical group 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- 206010040844 Skin exfoliation Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical group C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007257 malfunction Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-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
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- 229910017048 AsF6 Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229920006271 aliphatic hydrocarbon resin Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K77/00—Constructional details of devices covered by this subclass and not covered by groups H10K10/80, H10K30/80, H10K50/80 or H10K59/80
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Epoxy Resins (AREA)
- Electroluminescent Light Sources (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The image display device sealing material contains a resin component and a curing agent. The resin component contains an epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton.
Description
Technical Field
The present invention relates to an image display device sealing material.
Background
As an image display device including an optical element, for example, a liquid crystal display, an organic EL display, and the like are known. In such an image display device, in order to suppress deterioration of the optical element due to moisture or the like in the atmosphere, the optical element is sealed with a sealing member.
The sealing member can be formed, for example, by filling the optical element in the sealing composition and then curing the sealing composition. Therefore, various studies have been made on the composition of the sealing composition in order to impart properties required for various applications to the sealing member.
For example, a curable resin composition for sealing an organic electroluminescent display element, which contains a phenoxy resin, a cycloalkene oxide-type alicyclic epoxy compound, and a curing agent, has been proposed (for example, see patent document 1).
Documents of the prior art
Patent document
Patent document 1: international publication No. 2015/129670
Disclosure of Invention
Problems to be solved by the invention
However, when the sealing member formed of the curable resin composition for sealing an organic electroluminescent display element described in patent document 1 is used for a touch panel of an organic EL display, for example, the touch panel may malfunction due to noise caused by the sealing member because of its high dielectric constant.
The invention provides an image display device sealing material capable of forming a sealing member with low dielectric constant and ensured transparency.
Means for solving the problems
The present invention [1] comprises an image display device sealing material comprising a resin component and a curing agent, wherein the resin component comprises an epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton.
The invention [2] comprises the image display device sealing material according to [1], wherein the resin component further contains an epoxy resin containing a hydrogenated bisphenol A skeleton.
The invention [3] comprises the image display device sealing material according to [1] or [2], wherein the resin component further contains a biphenyl skeleton-containing epoxy resin having a weight average molecular weight of 800 or more and 100,000 or less.
ADVANTAGEOUS EFFECTS OF INVENTION
The image display device sealing material of the present invention can form a sealing member having a low dielectric constant and a high transparency because the resin component contains an epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton.
Drawings
Fig. 1 is a side sectional view of a seal sheet as an embodiment of the seal sheet for an image display device of the present invention.
Fig. 2 is a side sectional view of an organic EL display with a touch sensor as an embodiment (a mode having an In-Cell structure or an On-Cell structure) of an image display device including a sealing member formed of the sealing layer shown In fig. 1.
Fig. 3 is a side sectional view of an organic EL display with touch sensors as another embodiment (a mode having an Out-Cell structure) of an image display device.
Detailed Description
< embodiment 1 >
The image display device sealing material (hereinafter referred to as a sealing material) of the present invention is a sealing resin composition (sealing resin composition for an image display device) for sealing an optical element provided in an image display device described later, and is a curable resin composition which is cured to form a sealing member described later. The sealing material contains a resin component and a curing agent.
(1) Resin component
The resin component contains an epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton as an essential component.
(1-1) bisphenol alkyl-substituted cyclohexane skeleton-containing epoxy resin
The epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton has, for example, a plurality of bisphenol alkyl-substituted cyclohexane skeletons and a plurality of epoxy groups (polyfunctional (including 2-functional) type epoxy resins). The epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton preferably has a molecular chain containing a plurality of bisphenol alkyl-substituted cyclohexane skeletons and epoxy groups bonded to both ends of the molecular chain (2-functional epoxy resin).
The bisphenol alkyl-substituted cyclohexane skeleton has 1 or more alkyl groups (R) bonded to carbon atoms linking 2 benzene rings as shown in the following formula (1)1) A substituted cyclohexane ring.
The bisphenol alkyl-substituted cyclohexane skeleton is more preferably represented by the following formula (1).
Formula (1)
[ chemical formula 1]
[ in the formula (1), I, II and III are structural units, I and III are terminal units, respectively, and II is a repeating unit. R1Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]
With respect to R as the above formula (1)1Examples of the alkyl group include a straight-chain alkyl group having 1 to 6 carbon atoms (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl), a branched-chain alkyl group having 3 to 6 carbon atoms (e.g., isopropyl, isobutyl, tert-butyl, etc.), and the like.
R as the above formula (1)1Among the alkyl groups, a linear alkyl group having 1 to 6 carbon atoms is preferable, and a methyl group is more preferable. In addition, a plurality of R in the above formula (1)1May be the same or different from each other.
In the above formula (1), a plurality of R1In (1) at least1Is an alkyl group, preferably 2 or more R1Is alkyl, more preferably 3R1Is an alkyl group. In addition, a plurality of R1R other than alkyl1Is a hydrogen atom.
In the formula (1), the hydrogen atom of the benzene ring may be substituted with the above-mentioned alkyl group, but is preferably not substituted with the above-mentioned alkyl group.
Among such bisphenol alkyl-substituted cyclohexane skeletons, particularly preferred is an epoxy resin having a bisphenol trimethylcyclohexane skeleton represented by the following formula (2) (hereinafter referred to as an epoxy resin having a bisphenol TMC skeleton).
Formula (2)
[ chemical formula 2]
[ in the formula (2), I, II and III are structural units, I and III are terminal units, respectively, and II is a repeating unit. R1And R in the above formula (1)1The meaning is the same.]
The epoxy resin containing a bisphenol TMC skeleton represented by the above formula (2) is a copolymer of bisphenol TMC (4, 4' - (3,5, 5-trimethyl-1, 1-cyclohexanediyl) bis (phenol)) and epichlorohydrin, and has a molecular chain containing a plurality of bisphenol TMC skeletons and glycidyl ether units bonded to both ends of the molecular chain (2-functional epoxy resin).
The epoxy resin containing a bisphenol TMC skeleton represented by the above formula (2) is solid at room temperature. The term "solid at room temperature" means a solid state having no fluidity at room temperature (23 ℃), and the term "liquid at room temperature" means a liquid state having fluidity at room temperature (23 ℃) (the same applies hereinafter).
The bisphenol alkyl-substituted cyclohexane skeleton represented by the above formula (1) (the epoxy resin containing a bisphenol TMC skeleton represented by the above formula (2)) may contain other structural units in addition to the structural units I to III. Examples of the other structural units include a polyol unit derived from a polyol having two or more carbon atoms, a biphenyl unit derived from biphenyl, and the like.
The bisphenol alkyl-substituted cyclohexane skeleton has a weight average molecular weight (Mw) of, for example, 10,000 or more, preferably 12,000 or more, more preferably 15,000 or more, for example, 200,000 or less, preferably 150,000 or less. The weight average molecular weight (Mw) can be determined by Gel Permeation Chromatography (GPC) using polystyrene as a standard substance (the same applies hereinafter).
The epoxy equivalent in the bisphenol alkyl-substituted cyclohexane skeleton is, for example, 5,000 g/eq.or more, preferably 6,000 g/eq.or more, for example, 100,000 g/eq.or less, preferably 75,000 g/eq.or less.
Such epoxy resins having a bisphenol TMC skeleton may be used alone or in combination of 2 or more.
In the resin component, the content ratio of the epoxy resin containing a bisphenol TMC skeleton is, for example, 5 mass% or more, preferably 10 mass% or more, for example, 60 mass% or less, preferably 50 mass% or less, and more preferably 40 mass% or less.
(1-2) epoxy resin containing hydrogenated bisphenol A skeleton
The resin component preferably further contains, as an optional component, an epoxy resin having a hydrogenated bisphenol a skeleton.
The epoxy resin containing a hydrogenated bisphenol a skeleton is a hydrogenated product obtained by adding hydrogen to an epoxy resin containing a bisphenol a skeleton.
The hydrogenated bisphenol a skeleton-containing epoxy resin has, for example, a plurality of hydrogenated bisphenol a skeletons (specifically, 2, 2' -dicyclohexylpropane skeletons) and a plurality of epoxy groups (polyfunctional (including 2-functional) type epoxy resins). The hydrogenated bisphenol a skeleton-containing epoxy resin preferably has a molecular chain containing a plurality of hydrogenated bisphenol a skeletons and epoxy groups bonded to both ends of the molecular chain (2-functional epoxy resin).
The hydrogenated bisphenol a skeleton-containing epoxy resin is more preferably a hydrogenated product of a bisphenol a skeleton-containing epoxy resin which is a copolymer of bisphenol a and epichlorohydrin, and has a molecular chain containing a plurality of hydrogenated bisphenol a skeletons and glycidyl ether units (2-functional epoxy resin) bonded to both ends of the molecular chain. The epoxy resin containing a hydrogenated bisphenol A skeleton is solid at normal temperature.
The weight average molecular weight (Mw) of the hydrogenated bisphenol a skeleton-containing epoxy resin is, for example, 100 or more, preferably 150 or more, more preferably 200 or more, for example, 1,000 or less, preferably 800 or less.
The epoxy equivalent in the epoxy resin having a hydrogenated bisphenol A skeleton is, for example, 50 g/eq.or more, preferably 150 g/eq.or more, for example, 500 g/eq.or less, preferably 400 g/eq.or less.
Such an epoxy resin having a hydrogenated bisphenol a skeleton may be used alone or in combination of 2 or more.
In the resin component, the content of the epoxy resin having a hydrogenated bisphenol a skeleton is, for example, 30% by mass or more, preferably 40% by mass or more, more preferably 50% by mass or more, for example 80% by mass or less, preferably 70% by mass or less.
The content ratio of the hydrogenated bisphenol a skeleton-containing epoxy resin is, for example, 100 parts by mass or more, preferably 120 parts by mass or more, for example, 300 parts by mass or less, and preferably 200 parts by mass or less, based on 100 parts by mass of the total of the bisphenol alkyl-substituted cyclohexane skeleton-containing epoxy resin and a biphenyl skeleton-containing epoxy resin (described later) having a weight average molecular weight of 800 to 100,000.
(1-3) epoxy resin having Biphenyl skeleton
The resin component preferably further contains, as an optional component, an epoxy resin having a biphenyl skeleton with a weight average molecular weight of 800 or more and 100,000 or less.
The epoxy resin having a biphenyl skeleton has, for example, a plurality of biphenyl skeletons and a plurality of epoxy groups (polyfunctional (including 2-functional) type epoxy resins). The biphenyl skeleton-containing epoxy resin preferably has a molecular chain containing a plurality of biphenyl skeletons and epoxy groups bonded to both ends of the molecular chain (2-functional epoxy resin).
The biphenyl skeleton-containing epoxy resin is more preferably represented by the following formula (3).
Formula (3)
[ chemical formula 3]
[ in the formula (3), IV, V and VI are structural units, IV and VI respectively represent a terminal unit, and V represents a repeating unit. R2Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]
The biphenyl skeleton-containing epoxy resin represented by the above formula (3) is a copolymer of a dihydroxybiphenyl derivative and epichlorohydrin, and has a molecular chain containing a plurality of biphenyl skeletons and glycidyl ether units (2-functional epoxy resin) bonded to both ends of the molecular chain.
With respect to R as the above formula (3)2Examples of the alkyl group include the alkyl group represented by the above formula (1) and R1The same alkyl groups, and the like.
R in the above formula (3)2Among them, preferred areA hydrogen atom and a methyl group.
In addition, a plurality of R in the formula (3)2May be the same or different from each other.
In the above formula (3), a plurality of R2In (2), R bonded to the 3-and 5-positions of the benzene ring2Preferably an alkyl group, more preferably a methyl group. In addition, a plurality of R2In (2) and (6) R bonded to the benzene ring2Preferably a hydrogen atom.
The biphenyl type phenoxy resin represented by the above formula (3) may contain other structural units in addition to the structural units IV to VI. Examples of the other structural units include a polyol unit derived from a dihydric or higher polyol, a bisphenol unit derived from a bisphenol, and the like.
The biphenyl skeleton-containing epoxy resin has a weight average molecular weight (Mw) of 800 or more, preferably 1,000 or more, more preferably 2,000 or more and 100,000 or less, and preferably 90,000 or less.
The epoxy equivalent in the biphenyl skeleton-containing epoxy resin is, for example, 500 g/eq.or more, preferably 1,000 g/eq.or more, for example, 20,000 g/eq.or less, preferably 16,000 g/eq.or less.
Such epoxy resins having a biphenyl skeleton may be used alone or in combination of 2 or more.
In the resin component, the content of the biphenyl skeleton-containing epoxy resin is, for example, 5 mass% or more, preferably 10 mass% or more, for example, 50 mass% or less, preferably 30 mass% or less.
(1-4) optional resin component
The resin component may contain other resin components than the above-mentioned specific resin components (an epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton, an epoxy resin having a hydrogenated bisphenol a skeleton, and an epoxy resin having a biphenyl skeleton) within a range not to impair the effects of the present invention.
Examples of the other resin component include aliphatic hydrocarbon resins, styrene-based oligomers, bisphenol skeleton-containing epoxy resins (e.g., phenoxy resins), polyolefins (e.g., polyethylene, polybutadiene, etc.), polychloroprene, polyamides, polyamideimides, polyurethanes, polyethers, polyesters, silicone resins, and the like.
These other resin components may be used alone or in combination of 2 or more. The content of the other resin component in the resin component is, for example, 10 mass% or less, preferably 5 mass% or less.
The resin component is particularly preferably free of other resin components and is composed of an epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton, an epoxy resin having a hydrogenated bisphenol a skeleton, and an epoxy resin having a biphenyl skeleton.
(2) Curing agent
The curing agent polymerizes the resin component to cure the sealing material. The curing agent is not particularly limited as long as it can cure the sealing material. Examples of the curing agent include amine-based curing agents (e.g., diethylenetriamine, triethylenetetramine, tris (dimethylaminomethyl) phenol, etc.), imidazole-based curing agents (e.g., 2-methylimidazole, 2-ethyl-4-methylimidazole, etc.), acid anhydride-based curing agents (e.g., phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, etc.), thermal cationic curing agents, photo cationic curing agents, and the like. These curing agents may be used alone or in combination of 2 or more.
Among the curing agents, preferred examples include thermal cationic curing agents and photo cationic curing agents. That is, the curing agent preferably contains a thermal cationic curing agent and/or a photo cationic curing agent.
The thermal cationic curing agent and the photo cationic curing agent are not particularly limited, and each may be a compound capable of initiating polymerization of the above epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton, the above epoxy resin having a hydrogenated bisphenol a skeleton as required, and the above epoxy resin having a biphenyl skeleton.
The thermal cationic curing agent is a thermal acid generator that generates an acid (cation) by heating. The thermal cationic curing agent is preferably a compound that can initiate polymerization at a heat-resistant temperature of 120 ℃ or lower, for example, a display device (for example, an organic EL device).
As the thermal cationic curing agent, a known thermal cationic polymerization initiator can be used. As a thermal cationic polymerization initiatorHair-growing agent, for example AsF6 -、SbF6 -、PF6 -、BF4 -、B(C6F5)4 -、CF3SO3 -Sulfonium salts, phosphonium salts, quaternary ammonium salts, diazonium salts, iodonium salts, and the like, which are counter anions.
Among the thermal cationic curing agents, quaternary ammonium salts are preferred.
The photo cation curing agent is a photo acid generator that generates an acid (cation) by irradiation with light. As the photocationic curing agent, a known photocationic polymerization initiator can be used. Examples of the photo-cationic curing agent include CPI-210S (manufactured by San-Apro Ltd.), IK-1 (manufactured by San-Apro Ltd.), and the like.
These curing agents may be used alone or in combination of 2 or more.
The content of the curing agent is, for example, 0.3 parts by mass or more, preferably 0.5 parts by mass or more, for example, 10 parts by mass or less, preferably 5 parts by mass or less, per 100 parts by mass of the resin component.
(3) Other additives
The sealing material may contain, as other additives, a silane coupling agent, a leveling agent, a filler, a polymerization initiation aid, an antioxidant, a wettability improver, a surfactant, a plasticizer, an ultraviolet absorber, an antiseptic, an antibacterial agent, and the like at an appropriate ratio, as required.
< sealing sheet for image display device >
The sealing material can be directly distributed alone and is an industrially usable product, but from the viewpoint of operability, it is preferably distributed as a sealing sheet for an image display device.
A sealing sheet 1 as an embodiment of the sealing sheet for an image display device of the present invention will be described with reference to fig. 1.
As shown in fig. 1, the sealing sheet 1 includes a base film 3, a sealing layer 2 formed of the sealing material, and a release film 4 in this order in the thickness direction. The sealing sheet 1 is a member for manufacturing an image display device, and does not include a display element and a substrate on which the display element is mounted, and specifically, is a device which is formed of a sealing layer 2, a base film 3, and a release film 4, and in which the members are distributed individually and can be industrially used.
In order to prevent foreign matter from adhering to the sealing layer 2 and the like, the sealing layer 2 is preferably protected by the base film 3 and the release film 4 when the sealing sheet 1 is stored. When the sealing sheet 1 is used, the base film 3 and the release film 4 are peeled off.
The sealing layer 2 is a dried product of the above-described sealing material, and has a film shape (flat plate shape). Specifically, the sealing layer 2 has a predetermined thickness, extends in a predetermined direction orthogonal to the thickness direction, and has a flat front surface and a flat back surface.
In the sealing layer 2, the above resin components are not reacted, and the sealing layer 2 contains these resin components in an uncured state.
The thickness of the sealing layer 2 is, for example, 1 μm or more, preferably 5 μm or more, for example, 100 μm or less, preferably 30 μm or less.
Before the sealing sheet 1 is used for forming a sealing member (described later), the base film 3 is bonded to the back surface of the sealing layer 2 so as to be peelable, in order to support and protect the sealing layer 2. That is, the base film 3 is a flexible film of: the sealing sheet 1 is laminated on the back surface of the sealing layer 2 so as to cover the back surface of the sealing layer 2 at the time of shipment, transportation, and storage, and can be peeled off from the back surface of the sealing layer 2 so as to be bent into a substantially U shape immediately before the sealing sheet 1 is used.
The base film 3 has a flat plate shape, specifically, a predetermined thickness, extends in a predetermined direction orthogonal to the thickness direction, and has a flat front surface and a flat back surface. The bonding surface (surface) of the base film 3 may be subjected to a peeling treatment as needed.
Examples of the material of the base film 3 include resin materials such as polyester (e.g., polyethylene terephthalate (PET)), polyolefin (e.g., polyethylene, polypropylene, etc.), and preferably polyethylene terephthalate.
The base film 3 preferably includes a film having a moisture barrier property or a gas barrier property, and more preferably includes a film made of polyethylene terephthalate. The thickness of the base film 3 may be appropriately selected depending on the material of the film, but may be, for example, about 25 μm to 150 μm in view of compatibility with a material to be sealed such as a display device.
Before the sealing sheet 1 is used for forming a sealing member (described later), the release film 4 is bonded to the surface of the sealing layer 2 so as to be peelable in order to protect the sealing layer 2. Namely, the release film 4 is a flexible film of: the sealing sheet 1 is laminated on the surface of the sealing layer 2 so as to cover the surface of the sealing layer 2 at the time of shipment, transportation, and storage, and can be peeled off from the surface of the sealing layer 2 so as to be bent into a substantially U shape immediately before the sealing sheet 1 is used.
The release film 4 has a flat plate shape, specifically, a predetermined thickness, extends in a predetermined direction orthogonal to the thickness direction, and has a flat front surface and a flat back surface. The bonding surface (back surface) of the release film 4 may be subjected to a peeling treatment as needed. Examples of the material of the release film 4 include the same resin materials as those of the base film 3. The thickness of the release film 4 may be appropriately selected depending on the material of the film, but may be, for example, about 25 μm to 150 μm in view of compatibility with a material to be sealed such as a display device.
< method for producing sealing sheet for image display device >
Next, a method for manufacturing the sealing sheet 1 will be described.
To manufacture the sealing sheet 1, for example, the above-described sealing material is prepared, and the sealing material is applied to the surface of the base film 3 by a known method.
The sealing material can be prepared by mixing the above-mentioned resin component, curing agent and additive in the above-mentioned proportions. In the production of the sealing sheet 1, it is preferable to prepare a varnish of the sealing material by diluting the sealing material with an organic solvent.
The organic solvent is not particularly limited as long as the resin component and the curing agent can be uniformly dispersed or dissolved. Examples of the organic solvent include aromatic hydrocarbons (e.g., benzene, toluene, xylene, etc.), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), ethers (e.g., dibutyl ether, tetrahydrofuran, dioxane, ethylene glycol monoalkyl ether, ethylene glycol dialkyl ether, 1-methoxy-2-propanol, etc.), esters (e.g., ethyl acetate, butyl acetate, etc.), nitrogen-containing compounds (e.g., N-methylpyrrolidone, dimethylimidazolidinone, dimethyl formaldehyde, etc.), and the like. The organic solvent may be used alone or in combination of 2 or more.
The components can be dispersed by a ball mill, or charged into a flask and stirred, or kneaded by a three-roll mill, for example.
Further, examples of the method for applying the sealing material include screen printing, a dispenser (dispenser), and an application roller.
Next, the sealing material is dried, and the organic solvent is volatilized as necessary, thereby forming a coating film.
The heating temperature is a temperature at which the sealing material is dried without being cured, and is, for example, 20 ℃ or higher, preferably 90 ℃ or higher, for example 120 ℃ or lower, and preferably lower than 100 ℃. The heating time is, for example, 1 minute or more, preferably 2 minutes or more, for example, 30 minutes or less, preferably 15 minutes or less.
Thereby, the coating film is dried, and the sealing layer 2 formed of the sealing material can be prepared. Next, the release film 4 is attached to the surface of the sealing layer 2.
In the above manner, the sealing sheet 1 can be manufactured.
< manufacture of image display device >
Such a sealing sheet 1 can be suitably applied to sealing of (display element optical member) of an image display apparatus. An organic EL display with a touch sensor (hereinafter, referred to as an organic EL display 10) as an embodiment of an image display device will be described with reference to fig. 2.
In this embodiment, an organic EL display with a touch sensor is given as an image display device, but the image display device is not particularly limited. Examples of the image display device include a liquid crystal display (including a liquid crystal display with a touch sensor), an organic EL display (including an organic EL display with a touch sensor), and the like.
The organic EL display 10 includes an element mounting unit 11, a sealing member 14, and cover glass or a barrier film 15.
The element-mounting unit 11 includes a substrate 13, an organic EL element 12 as an example of a display element, a barrier layer 16, and an electrode (not shown).
The substrate 13 supports the organic EL element 12. The substrate 13 preferably has flexibility.
The organic EL element 12 is a known organic EL element and is mounted on the substrate 13. The organic EL element 12 includes a cathode reflective electrode, an organic EL layer, and an anode transparent electrode, although not shown.
The barrier layer 16 covers the organic EL element 12 and suppresses contact of moisture in the atmosphere with the organic EL element 12. The barrier layer 16 includes a 1 st inorganic barrier layer 17, a planarizing layer 19, and a 2 nd inorganic barrier layer 18.
The 1 st inorganic barrier layer 17 is disposed on the upper surface and the side surfaces of the organic EL element 12 so as to surround the organic EL element 12. Examples of the material of the 1 st inorganic barrier layer 17 include metal oxides (e.g., aluminum oxide, silicon oxide, copper oxide, etc.), metal nitrides (e.g., aluminum nitride, silicon nitride, etc.), and the like. The material of the 1 st inorganic barrier layer 17 may be used alone or in combination of 2 or more. Among the materials of the 1 st inorganic barrier layer 17, a metal nitride is preferable, and silicon nitride is more preferable.
The planarization layer 19 is disposed on the upper surface of the 1 st inorganic barrier layer 17. As a material of the planarizing layer 19, a known resin material can be given.
The 2 nd inorganic barrier layer 18 is disposed on the upper surface and the side surface of the planarization layer 19 so as to surround the planarization layer 19. Examples of the material of the 2 nd inorganic barrier layer 18 include the same materials as those of the 1 st inorganic barrier layer 17.
The electrodes (not shown) constitute sensors of the organic EL display with touch sensors. An electrode (not shown) is located between the substrate 13 and the sealing member 14. For example, the electrode (not shown) may be located within the substrate 13 or may be located on the organic EL element 12.
The sealing member 14 is a cured product of the sealing layer 2 (sealing material), and seals the organic EL element 12 covered with the barrier layer 16. The sealing member 14 is formed of the sealing layer 2 from which the base film 3 and the release film 4 are peeled. Specifically, the sealing layer 2 from which the base film 3 and the release film 4 are peeled off is attached to the substrate 13 so as to fill the organic EL element 12 covered with the barrier layer 16, then a cover glass or a barrier film 15 is attached to the upper surface of the sealing layer 2, and then the sealing layer 2 is cured. Thereby, the sealing member 14 can be formed.
The dielectric constant of the sealing member 14 is, for example, 3.0 or more, preferably 3.2 or more, for example, less than 3.80, preferably 3.70 or less. The dielectric constant can be measured by the method described in the examples described below.
When the dielectric constant of the sealing member 14 is not less than the lower limit, the degree of freedom in selecting a material can be improved. When the dielectric constant of the sealing member 14 is not more than the upper limit, it is possible to suppress the occurrence of malfunction in an organic EL display or the like with a touch sensor.
The moisture permeability of the sealing member 14 is, for example, 20g/m224h or more, e.g. less than 45g/m224 h. The moisture permeability can be measured by the method described in the examples described later.
If the moisture permeability of the sealing member 14 is not more than the upper limit, deterioration of the optical element sealed by the sealing member 14 can be suppressed.
The cover glass or the barrier film 15 is disposed on the upper surface of the sealing member 14. The cover glass or the barrier film 15 includes, although not shown, a glass plate and electrodes provided on the lower surface of the glass plate and constituting sensors of the organic EL display with touch sensors.
Such an organic EL display 10 has an In-Cell structure In which the organic EL elements 12 are arranged between 2 electrodes constituting the sensor, or an On-Cell structure In which 1 of the 2 electrodes constituting the sensor is arranged On the organic EL elements 12.
< Effect >
However, the sealing member of the liquid crystal display may be provided in a frame shape so as to surround the liquid crystal disposed between the substrate and the glass plate, for example. In contrast, the sealing member of the organic EL display is provided so that the organic EL element is buried therein as shown in fig. 2. Therefore, the sealing member of the organic EL display has a larger influence on the dielectric constant than the sealing member of the liquid crystal display, and it is desired to reduce the dielectric constant.
On the other hand, the sealing member of the organic EL display does not require a low dielectric constant to the extent required for a sealing member of a general semiconductor component.
The inventors of the present application have made various studies on the composition of the resin component and found the following findings, thereby completing the present invention: by incorporating an epoxy resin containing a bisphenol alkyl-substituted cyclohexane skeleton into the resin component of the sealing material, not only can the dielectric constant be reduced in the sealing member, but also high transparency can be ensured.
In the above-mentioned sealing material, since the resin component contains an epoxy resin containing a bisphenol alkyl-substituted cyclohexane skeleton, it is possible to reduce the dielectric constant in the sealing member to a range required for an image display device (particularly, an organic EL display), and to ensure high transparency required for an image display device (particularly, an organic EL display).
Further, as shown in fig. 1, the sealing sheet 1 has a sealing layer 2 formed of a sealing material. Therefore, the workability of the sealing material can be improved. In addition, the sealing member can ensure high transparency while reducing the dielectric constant.
< embodiment 2 >
Next, embodiment 2 of the sealing material will be explained.
In embodiment 1 described above, the resin component preferably contains the above-described epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton (epoxy resin having a bisphenol TMC skeleton) and the above-described epoxy resin having a biphenyl skeleton, but the present invention is not limited thereto.
In embodiment 2, the resin component contains a copolymer of a monomer having a bisphenol alkyl-substituted cyclohexane skeleton (e.g., bisphenol TMC) and an epoxy monomer having a biphenyl skeleton (e.g., tetramethylbiphenyl diglycidyl ether). The resin component preferably contains a copolymer of bisphenol TMC and tetramethylbiphenyl diglycidyl ether.
Such a copolymer has a plurality of bisphenol alkyl-substituted cyclohexane skeletons (bisphenol TMC skeleton), a plurality of biphenyl skeletons, and a plurality of epoxy groups (polyfunctional (including 2-functional) type epoxy resins). Therefore, such a copolymer corresponds to an epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton (an epoxy resin having a bisphenol TMC skeleton), more specifically, to an epoxy resin having a bisphenol TMC skeleton-biphenyl skeleton.
Such a copolymer particularly preferably has a molecular chain including a plurality of bisphenol TMC skeletons and a plurality of biphenyl skeletons, and epoxy groups (glycidyl ether units) (2-functional epoxy resins) bonded to both ends of the molecular chain.
In the resin component, the content ratio of the copolymer of the bisphenol alkyl-substituted cyclohexane skeleton-containing monomer and the biphenyl skeleton-containing epoxy monomer is, for example, 10 mass% or more, preferably 30 mass% or more, for example, 70 mass% or less, preferably 60 mass% or less, and more preferably 50 mass% or less.
In embodiment 2, the resin component preferably contains an epoxy resin having a hydrogenated bisphenol a skeleton, as described above. On the other hand, the resin component may contain an epoxy resin having a biphenyl skeleton, but preferably does not contain an epoxy resin having a biphenyl skeleton.
That is, in embodiment 2, the resin component is preferably composed of a copolymer of a monomer having a bisphenol alkyl-substituted cyclohexane skeleton and an epoxy monomer having a biphenyl skeleton, and an epoxy resin having a hydrogenated bisphenol a skeleton.
The operation and effect similar to those of the above-described embodiment 1 can be achieved by the above-described embodiment 2.
The resin component may contain a copolymer of the epoxy resin having a bisphenol alkyl-substituted cyclohexane skeleton of embodiment 1 (preferably, the epoxy resin having a bisphenol TMC skeleton represented by formula (2)) and the epoxy resin having a biphenyl skeleton of embodiment 1 (preferably, the epoxy resin having a biphenyl skeleton represented by formula (3)).
< modification example >
In the modification, the same members and steps as those in embodiment 1 described above are denoted by the same reference numerals, and detailed description thereof is omitted.
As shown in fig. 1, the sealing sheet 1 includes a sealing layer 2, a base film 3, and a release film 4, but the image display device sealing sheet is not limited thereto. The image display device sealing sheet may be provided with the sealing layer 2, and may not include the base film 3 and/or the release film 4. That is, the image display device sealing sheet may be constituted only by the sealing layer 2, or may include the sealing layer 2, and any one of the foundation film 3 and the release film 4.
As shown in fig. 2, the organic EL display 10 includes the barrier layer 16, but is not limited thereto. The organic EL display 10 may not have the barrier layer 16.
The organic EL display 10 has an In-Cell structure In which the organic EL elements 12 are arranged between 2 electrodes constituting the sensor, or an On-Cell structure In which 1 of the 2 electrodes is arranged On the organic EL elements 12, but is not limited thereto.
For example, as shown in fig. 3, the organic EL display 20 may have an Out-Cell structure in which 2 electrodes constituting a sensor are arranged on the upper side of the sealing member 14. The organic EL display 20 includes the element mounting unit 11, the sealing member 14, and the sensor unit 25.
The sensor unit 25 is disposed on the sealing member 14. The sensor unit 25 includes electrodes constituting a sensor of the organic EL display with a touch sensor. In the organic EL display 20, the substrate 13 does not include an electrode.
The above modifications also have the same operational advantages as the above embodiment. The above embodiments and modifications can be combined as appropriate.
Examples
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto. Specific numerical values such as blending ratios (content ratios), physical property values, and parameters used in the following description may be replaced with upper limit values (numerical values defined as "lower" and "lower") or lower limit values (numerical values defined as "upper" and "higher") described in association with the corresponding blending ratios (content ratios), physical property values, and parameters described in the above-described "embodiment". Unless otherwise specified, "part(s)" and "%" are based on mass.
Synthesis example 1
Into a flask equipped with a stirrer, a thermometer, a nitrogen-blowing tube and a cooling tube, 100 parts by mass of bisphenol TMC, 140 parts by mass of bisphenol TMC diglycidyl ether (the ratio of the number of moles of epoxy groups to the number of moles of phenolic hydroxyl groups is 1.03), and 15 parts by mass of cyclohexanone as a reaction solvent were charged, and the temperature was raised to 100 ℃ under a nitrogen atmosphere. Next, 0.1 part by mass of methyltriphenylphosphonium bromide (TMP) as a catalyst was further charged into the flask, and the internal temperature of the flask was increased to 140 ℃. Since the reaction solution started to become viscous as the reaction proceeded, 75 parts by mass of cyclohexanone was added to the reaction solution, and the reaction was carried out for 12 hours. The reaction temperature is 140 to 145 ℃ when the nonvolatile content is 80% by mass or more, and the reflux temperature is not higher than that. After the reaction was completed, 200 parts by mass of methyl ethyl ketone was added to the reaction solution to obtain a resin varnish containing an epoxy resin having a bisphenol TMC skeleton.
Synthesis example 2
Into a flask equipped with a stirrer, a thermometer, a nitrogen-blowing tube and a cooling tube, 100 parts by mass of bisphenol TMC, 118 parts by mass of tetramethylbiphenyl diglycidyl ether (the ratio of the number of moles of epoxy groups to the number of moles of phenolic hydroxyl groups is 1.03) and 15 parts by mass of cyclohexanone as a reaction solvent were charged, and the temperature was raised to 100 ℃ under a nitrogen atmosphere. Next, 0.1 part by mass of TMP as a catalyst was further charged into the flask, and then the internal temperature of the flask was increased to 140 ℃. Since the reaction solution started to become viscous as the reaction proceeded, 75 parts by mass of cyclohexanone was added to the reaction solution, and the reaction was carried out for 12 hours. The reaction temperature is 140 to 145 ℃ when the nonvolatile content is 80% or more, and the reflux temperature is 140 to 145 ℃ or less. After the reaction was completed, 200 parts by mass of methyl ethyl ketone was added to the reaction solution to obtain a resin varnish containing an epoxy resin having a bisphenol TMC skeleton (an epoxy resin having a bisphenol TMC skeleton-biphenyl skeleton).
Examples 1 and 2
The epoxy resin having a bisphenol TMC skeleton, the epoxy resin having a hydrogenated bisphenol A skeleton (trade name: YX8000, manufactured by Mitsubishi Chemical Corporation, weight average molecular weight: 352, epoxy equivalent: 205g/eq.) and the epoxy resin having a biphenyl skeleton (trade name: YX6954BH30, manufactured by Mitsubishi Chemical Corporation, manufactured by the above formula (3)) obtained in each synthetic example shown in Table 1 were mixed in the formulation shown in Table 1 (in terms of solid content)2Hydrogen atom and methyl group, weight average molecular weight: 39,000, epoxy equivalent: 10,000 to 16,000g/eq.), and a thermal cationic curing agent (trade name: CXC-1612 manufactured by King Industries, Ltd.) was mixed to prepare a sealing material.
Examples 3 and 4
A sealing material was produced in the same manner as in examples 1 and 2, except that the thermal cationic curing agent was changed to a photo cationic curing agent (trade name: CPI-210S, manufactured by San-Apro Ltd.).
Comparative example 1
Bisphenol-type phenoxy resin (trade name: jER4275, manufactured by Mitsubishi Chemical Corporation, containing bisphenol A skeleton and bisphenol F skeleton, epoxy equivalent: 8,400 to 9,200g/eq.), cycloolefin-oxide-type epoxy resin (trade name: CELLOXIDE 2021P, (3, 4-epoxy) cyclohexanecarboxylic acid 3, 4-epoxycyclohexylmethyl ester, molecular weight: 252.3, epoxy equivalent: 128 to 145g/eq.), solid epoxy resin (trade name: jER4005P, manufactured by Mitsubishi Chemical Corporation, epoxy equivalent: 1070g/eq.), and thermal cationic curing agent (trade name: CXC-1612, manufactured by King Industries) were mixed in the formulation shown in Table 1 (in terms of solid content) to prepare a sealant.
Comparative example 2
Except that the bisphenol type phenoxy resin was changed to an epoxy resin having a biphenyl skeleton (trade name: YX6954BH30, manufactured by Mitsubishi Chemical Corporation, in the above formula (3), R2Hydrogen atom and methyl group, weight average molecular weight: 39,000, epoxy equivalent: 10,000 to 16,000g/eq.) was prepared in the same manner as in comparative example 1.
Comparative example 3
In the formulation shown in Table 1 (in terms of solid content), a bisphenol type phenoxy resin (trade name: JeR4275, manufactured by Mitsubishi Chemical Corporation, containing a bisphenol A skeleton and a bisphenol F skeleton and having an epoxy equivalent of 8,400 to 9,200g/eq.), an epoxy resin containing a hydrogenated bisphenol A skeleton (trade name: YX8000, manufactured by Mitsubishi Chemical Corporation, having a weight average molecular weight of 352 and an epoxy equivalent of 205g/eq.), and a thermal cationic initiator (trade name: CXC-1612, manufactured by King Industries) were mixed to prepare a sealing material.
< evaluation >
Dielectric constant
The sealing materials of the examples and comparative examples were applied to a PET film (a mold-released PET film, trade name: Purex A53, manufactured by DuPont Teijin Films, thickness: 38 μm, base film) by a coater, and then dried at 90 ℃ for 3 minutes by purging the furnace with nitrogen gas to form a sealing layer having a thickness of 15 μm.
Next, a PET film (a mold-released PET film, trade name: Purex A31, manufactured by DuPont Teijin Films, thickness: 38 μm, mold-released film) was bonded to the sealant layer at 80 ℃ by a hot laminator.
In the above manner, a sealing sheet provided with a base film, a sealing layer, and a release film was prepared. The above-described operation was repeated, and 2 sealing sheets were prepared for each of the examples and comparative examples. After the release film was peeled off from the sealant layer, 2 sealant layers were bonded to each other in the thickness direction so that the thicknesses thereof became 30 μm for 2 sealant sheets corresponding to the same examples or comparative examples.
Next, with respect to 2 sealant layers laminated to each other, the base film on one side was peeled off and cured at 100 ℃ for 1 hour, and then the base film on the other side was peeled off from the cured sealant layer to obtain a sample for measurement. The dielectric constant of the obtained sample was measured at 100kHz by an auto-balance bridge method using an LCR tester HP4284A (manufactured by Agilent Technologies).
Then, the dielectric constant was evaluated by the following criteria. The results are shown in table 1.
O: less than 3.80
X: 3.80 or more.
Moisture permeability
In the same manner as in the above evaluation of dielectric constant, sealing sheets of examples and comparative examples were prepared. Then, the release film was peeled off from the sealant layer, and then the sealant layer was cured at 100 ℃ for 1 hour.
Next, the base film was peeled off from the cured sealing layer to obtain a sample for measurement. The moisture permeability (moisture permeability) of the obtained sample was measured at 60 ℃ and 90% RH in accordance with JIS Z0208. Then, the film thickness of the sample used for the measurement was converted into a value when the thickness of the sample was 100 μm.
Then, the moisture permeability was evaluated by the following criteria. The results are shown in table 1.
O: less than 45g/m2·24h
△：45g/m224h or more.
[ Table 1]
It should be noted that the above-mentioned invention is provided as an exemplary embodiment of the present invention, which is only an example and is not to be construed as a limitation. Modifications of the present invention that are obvious to those skilled in the art are also encompassed by the appended claims.
Industrial applicability
The image display device sealing material of the present invention can be suitably used as a sealing material for various image display devices, specifically, a sealing material for liquid crystal displays, organic EL displays, and the like.
Description of the reference numerals
1 sealing sheet
2 sealing layer
Claims (3)
1. An image display device sealing material comprising a resin component and a curing agent,
the resin component contains an epoxy resin containing a bisphenol alkyl-substituted cyclohexane skeleton.
2. The image display device sealing material according to claim 1, wherein the resin component further contains an epoxy resin having a hydrogenated bisphenol a skeleton.
3. The image display device sealing material according to claim 1, wherein the resin component further contains a biphenyl skeleton-containing epoxy resin having a weight average molecular weight of 800 or more and 100,000 or less.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019145960A JP2019206717A (en) | 2019-08-08 | 2019-08-08 | Image display device sealing material |
| JP2019-145960 | 2019-08-08 | ||
| PCT/JP2020/023136 WO2021024616A1 (en) | 2019-08-08 | 2020-06-12 | Image display apparatus sealing material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112673065A true CN112673065A (en) | 2021-04-16 |
Family
ID=68767429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080003491.9A Pending CN112673065A (en) | 2019-08-08 | 2020-06-12 | Sealing material for image display device |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JP2019206717A (en) |
| KR (1) | KR102452783B1 (en) |
| CN (1) | CN112673065A (en) |
| WO (1) | WO2021024616A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7368202B2 (en) * | 2019-11-29 | 2023-10-24 | リンテック株式会社 | Sealing sheet |
| JP2022182017A (en) * | 2021-05-27 | 2022-12-08 | 双葉電子工業株式会社 | Curable resin composition and organic EL element |
| WO2024026420A1 (en) * | 2022-07-29 | 2024-02-01 | Arialys Therapeutics, Inc. | Methods and systems for identifying or treating central nervous systems disease |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW561162B (en) * | 2003-06-11 | 2003-11-11 | Chang Chun Plastics Co Ltd | Epoxy resin composition for encapsulation of optical semiconductor device |
| JP2007046035A (en) * | 2005-01-26 | 2007-02-22 | Sekisui Chem Co Ltd | Encapsulant for organic electroluminescent device, method for producing organic electroluminescent display and organic electroluminescent display |
| JP2009249569A (en) * | 2008-04-09 | 2009-10-29 | Japan Epoxy Resin Kk | Epoxy resin composition for optical element sealing material |
| CN104813741A (en) * | 2012-11-28 | 2015-07-29 | 日本化药株式会社 | Resin composition, and cured product (1) thereof |
| CN107922742A (en) * | 2015-08-31 | 2018-04-17 | 日本瑞翁株式会社 | Resin combination |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4887746B2 (en) * | 2005-11-11 | 2012-02-29 | 三菱化学株式会社 | Hydrogenated epoxy resin, method for producing the same, epoxy resin composition, and epoxy resin composition for light emitting device sealing material |
| JPWO2014017524A1 (en) * | 2012-07-26 | 2016-07-11 | デンカ株式会社 | Resin composition |
| JP6549984B2 (en) | 2014-02-27 | 2019-07-24 | 積水化学工業株式会社 | Curable resin composition for sealing an organic electroluminescence display device, curable resin sheet for sealing an organic electroluminescence display device, and an organic electroluminescence display device |
| JP6620743B2 (en) * | 2014-07-04 | 2019-12-18 | 三菱ケミカル株式会社 | Resin, photosensitive resin composition, cured product, color filter, and image display device |
| KR20170033886A (en) * | 2014-07-22 | 2017-03-27 | 사빅 글로벌 테크놀러지스 비.브이. | High heat monomers and methods of use thereof |
| JP6878076B2 (en) * | 2017-03-24 | 2021-05-26 | 日鉄ケミカル＆マテリアル株式会社 | Oxazoridone ring-containing epoxy resin composition, its production method, curable resin composition, and cured product |
-
2019
- 2019-08-08 JP JP2019145960A patent/JP2019206717A/en active Pending
-
2020
- 2020-06-12 KR KR1020207037370A patent/KR102452783B1/en active IP Right Grant
- 2020-06-12 CN CN202080003491.9A patent/CN112673065A/en active Pending
- 2020-06-12 JP JP2020570991A patent/JP6896190B1/en active Active
- 2020-06-12 WO PCT/JP2020/023136 patent/WO2021024616A1/en active Application Filing
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW561162B (en) * | 2003-06-11 | 2003-11-11 | Chang Chun Plastics Co Ltd | Epoxy resin composition for encapsulation of optical semiconductor device |
| US20040254305A1 (en) * | 2003-06-11 | 2004-12-16 | Kuen-Yuan Hwang | Epoxy resin composition for photosemiconductor package |
| JP2007046035A (en) * | 2005-01-26 | 2007-02-22 | Sekisui Chem Co Ltd | Encapsulant for organic electroluminescent device, method for producing organic electroluminescent display and organic electroluminescent display |
| JP2009249569A (en) * | 2008-04-09 | 2009-10-29 | Japan Epoxy Resin Kk | Epoxy resin composition for optical element sealing material |
| CN104813741A (en) * | 2012-11-28 | 2015-07-29 | 日本化药株式会社 | Resin composition, and cured product (1) thereof |
| CN107922742A (en) * | 2015-08-31 | 2018-04-17 | 日本瑞翁株式会社 | Resin combination |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2021024616A1 (en) | 2021-09-13 |
| JP2019206717A (en) | 2019-12-05 |
| WO2021024616A1 (en) | 2021-02-11 |
| KR20210018320A (en) | 2021-02-17 |
| TW202112873A (en) | 2021-04-01 |
| KR102452783B1 (en) | 2022-10-07 |
| JP6896190B1 (en) | 2021-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110603277B (en) | Image display device sealing material and image display device sealing sheet | |
| KR101913603B1 (en) | Epoxy resin composition, cured product thereof, and curable resin composition | |
| CN112673065A (en) | Sealing material for image display device | |
| TWI511996B (en) | Curable epoxy resin composition | |
| WO2015129670A1 (en) | Curable resin composition for sealing organic electroluminescent display element, curable resin sheet for sealing organic electroluminescent display element, and organic electroluminescent display element | |
| JP2016536410A (en) | Curable composition for electronic devices and use thereof | |
| SG172173A1 (en) | Carboxylic acid compound and epoxy resin composition containing same | |
| EP3406645B1 (en) | Epoxy resin composition | |
| KR20140022828A (en) | Polycarboxylic acid resin and composition thereof | |
| KR20150063368A (en) | Polycarboxylic acid resin and epoxy resin composition | |
| WO2015087807A1 (en) | Curable resin composition for sealing organic electroluminescent display element, curable resin sheet for sealing organic electroluminescent display element, and organic electroluminescent display element | |
| CN110741046B (en) | Image display device sealing material and image display device sealing sheet | |
| JP2000007891A (en) | New liquid epoxy resin composition, its cured product and semiconductor sealing device | |
| KR20120061832A (en) | Thermosetting resin composition for surface protection layers | |
| TWI843867B (en) | Image display device sealing material | |
| KR20150082188A (en) | Epoxy resin mixture, epoxy resin composition, and cured product thereof | |
| WO2020080292A1 (en) | Curable resin composition, cured product, and sheet-form molded article | |
| WO2022080372A1 (en) | Display element sealing material, organic el element sealing material, and display element sealing sheet | |
| KR20170040940A (en) | Photocurable adhesive composition | |
| JP6376692B2 (en) | Carboxylic anhydride group-containing cyclic siloxane compound, epoxy resin composition containing the same, and cured product thereof | |
| WO2024116693A1 (en) | Resin composition, adhesive, sealing material, die attachment material, cured product and electronic device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |