JP7445714B2 - 有機発光素子の封止材用熱硬化性液状組成物 - Google Patents
有機発光素子の封止材用熱硬化性液状組成物 Download PDFInfo
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- JP7445714B2 JP7445714B2 JP2022123753A JP2022123753A JP7445714B2 JP 7445714 B2 JP7445714 B2 JP 7445714B2 JP 2022123753 A JP2022123753 A JP 2022123753A JP 2022123753 A JP2022123753 A JP 2022123753A JP 7445714 B2 JP7445714 B2 JP 7445714B2
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- 229920001187 thermosetting polymer Polymers 0.000 title claims description 42
- 239000000203 mixture Substances 0.000 title claims description 40
- 239000007788 liquid Substances 0.000 title claims description 33
- 239000008393 encapsulating agent Substances 0.000 title claims description 21
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- 239000000463 material Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000003566 sealing material Substances 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 20
- 125000002723 alicyclic group Chemical group 0.000 claims description 15
- 125000002091 cationic group Chemical group 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- PLDLPVSQYMQDBL-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethoxy)-2,2-bis(oxiran-2-ylmethoxymethyl)propoxy]methyl]oxirane Chemical compound C1OC1COCC(COCC1OC1)(COCC1OC1)COCC1CO1 PLDLPVSQYMQDBL-UHFFFAOYSA-N 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- 238000002834 transmittance Methods 0.000 claims description 7
- 230000001588 bifunctional effect Effects 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 238000005538 encapsulation Methods 0.000 claims description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims description 3
- 230000002123 temporal effect Effects 0.000 claims description 2
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 claims 1
- -1 6-methyl-3,4-epoxycyclohexylmethyl (6-methyl- 3,4-epoxy)cyclohexanecarboxylate Chemical compound 0.000 description 17
- 230000008859 change Effects 0.000 description 13
- 239000011521 glass Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 238000001723 curing Methods 0.000 description 8
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- 230000032683 aging Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000003230 hygroscopic agent Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 1
- NQEJEMZJOBCYOD-UHFFFAOYSA-N (4-methoxyphenyl)methyl-dimethyl-phenylazanium Chemical compound C1=CC(OC)=CC=C1C[N+](C)(C)C1=CC=CC=C1 NQEJEMZJOBCYOD-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-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
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- PUZHXYSDMURDFB-UHFFFAOYSA-N O(CCOCCOCCOC)C(CCCOCCOCCOBOCCOCCOCCOCCOC)OCCOCCOCCOC Chemical compound O(CCOCCOCCOC)C(CCCOCCOCCOBOCCOCCOCCOCCOC)OCCOCCOCCOC PUZHXYSDMURDFB-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 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
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- NIYNIOYNNFXGFN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol;7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound OCC1CCC(CO)CC1.C1C(C(=O)O)CCC2OC21.C1C(C(=O)O)CCC2OC21 NIYNIOYNNFXGFN-UHFFFAOYSA-N 0.000 description 1
- VPSDPCXOOHMTDQ-UHFFFAOYSA-N [B+3].C(C)[N+](C1=CC=CC=C1)(CC1=CC=CC=C1)CC Chemical compound [B+3].C(C)[N+](C1=CC=CC=C1)(CC1=CC=CC=C1)CC VPSDPCXOOHMTDQ-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- IOVVFSGCNWQFQT-UHFFFAOYSA-N bis(2,3,4,5,6-pentafluorophenyl) carbonate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OC(=O)OC1=C(F)C(F)=C(F)C(F)=C1F IOVVFSGCNWQFQT-UHFFFAOYSA-N 0.000 description 1
- HVXJOTGWBBSEBT-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-3-yl) oxalate Chemical compound C(C(=O)OC1CC2C(CC1)O2)(=O)OC1CC2C(CC1)O2 HVXJOTGWBBSEBT-UHFFFAOYSA-N 0.000 description 1
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 1
- HYVNJCOHGOONJK-UHFFFAOYSA-N dibenzyl-methyl-phenylazanium Chemical compound C=1C=CC=CC=1C[N+](C=1C=CC=CC=1)(C)CC1=CC=CC=C1 HYVNJCOHGOONJK-UHFFFAOYSA-N 0.000 description 1
- ONRGBXGMVZEZLY-UHFFFAOYSA-N dimethyl-[(4-methylphenyl)methyl]-phenylazanium Chemical compound C1=CC(C)=CC=C1C[N+](C)(C)C1=CC=CC=C1 ONRGBXGMVZEZLY-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910021426 porous silicon Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- IJJNTMLAAKKCML-UHFFFAOYSA-N tribenzyl borate Chemical compound C=1C=CC=CC=1COB(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 IJJNTMLAAKKCML-UHFFFAOYSA-N 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- DLVYHYUFIXLWKV-UHFFFAOYSA-N tris(2-ethylhexyl) borate Chemical compound CCCCC(CC)COB(OCC(CC)CCCC)OCC(CC)CCCC DLVYHYUFIXLWKV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
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- 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
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- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—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 catalysts used
- C08G59/688—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 catalysts used containing phosphorus
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- 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
- H10K50/842—Containers
- H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants
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- 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
- H10K50/846—Passivation; Containers; Encapsulations comprising getter material or desiccants
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
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- Epoxy Resins (AREA)
- Electroluminescent Light Sources (AREA)
Description
本発明で使用され得る脂環族二官能エポキシ系化合物は、例えば、ビス(3,4-エポキシシクロヘキシル)オキサレート;ビス(3,4-エポキシシクロヘキシルメチル)アジペート;ビス(3,4-エポキシ-6-メチルシクロヘキシルメチル)アジペート;3,4-エポキシシクロヘキシルメチル(3,4-エポキシ)シクロヘキサンカルボキシレート;3,4-エポキシシクロヘキサンカルボキシレート;6-メチル-3,4-エポキシシクロヘキシルメチル(6-メチル-3,4-エポキシ)シクロヘキサンカルボキシレート;3,4-エポキシ-2-メチルシクロヘキシルメチル(3,4-エポキシ-2-メチル)シクロヘキサンカルボキシレート;3,4-エポキシ-3-メチルシクロヘキシルメチル(3,4-エポキシ-3-メチル)シクロヘキサンカルボキシレート;3,4-エポキシ-5-メチルシクロヘキシルメチル(3,4-エポキシ-5-メチル)シクロヘキサンカルボキシレート;3,4-エポキシシクロヘキシルメチル-3’,4’-エポキシシクロヘキサンカルボキシレート変形されたイプシロン-カプロラクトン(epoxycyclohexanecarboxylate modified epsilon-caprolactone);及び(3’,4’-エポキシシクロヘキサン)メチル3,4-エポキシシクロヘキシルカルボキシレートからなる群より選択された一種以上であってもよい。
本発明のカチオン性熱硬化開始剤は、エポキシバインダー物質の重合反応を促進し、また、硬化条件下での完全硬化及び貯蔵安定性を向上させるための添加剤である。
本発明の経時安定剤は、硬化温度未満の環境(25~40℃)で、液状組成物の経時変化を抑制(粘度上昇を防止)して、貯蔵安定性を向上させるための添加剤である。
本発明の界面活性剤は、有機発光素子のガラス上に封止材を適用するとき、封止用組成物が硬化して形成される樹脂の広がり性及び表面張力を調節するための添加剤である。
下記の表1に記載したように、エポキシバインダーとしてのPETG100重量部を基準に、カチオン性熱硬化開始剤を2.0重量部で混合して、硬化していない液状混合組成物を準備した。
実施例1と同様に実施するものの、実施例2~5は、PETGのほか、脂環族二官能エポキシ系化合物をさらに混合して、経時安定剤と界面活性剤をさらに使用しており、実施例4~5は、カチオン性熱硬化開始剤の含量を2.1重量部に変更して実施した。実施例1~5の液状混合組成物の組成及び含量は、下記の表1に示した。
比較例1は、実施例2と同様に実施するものの、PETGを40重量部で含み、脂環族二官能エポキシ系化合物を60重量部で含めた点で相違する。
吸湿率は、実施例1で得た液状混合組成物に水分を加えたとき、重さ変化率として評価し、高温及び高湿条件での信頼性評価後、重さ変化率及び前記信頼性評価に続いて、高温熱処理後の重さ変化率を計算した。具体的な方法及び重さ変化率の計算方法は、次のとおりである。
(式2)信頼性評価及び高温処理後の重さ変化率=[([4]-[1])-([2]-[1])]/([2]-[1])×100%
無アルカリガラスを準備して、その上に前記実施例1で得た液状混合組成物を0.1g塗布した後、他の無アルカリガラスをその上に貼り合わせた。貼り合わせた状態で、高温オーブンで、100℃/1hrの条件で、1時間熱硬化を行って、サンプルを製作した。前記サンプルをヘイズメーター(Haze Meter)装備(NDH-7000)に位置させて、ASTM D 1003測定方法により光透過率及びヘイズを同時に測定した。
貯蔵安定性は、初期粘度に対し、40℃で保管後、毎日粘度変化率を評価した。粘度測定方法では、前記実施例1で得た液状混合組成物をBrookfield社のCone&plate粘度計装備を下記の条件に設定した後、sample cupに塗布した後、粘度を確認して記録した。
-温度:25℃
-速度:10rpm
-試料投入量:0.5ml(トルク:30~60%)
-B:3,4-エポキシシクロヘキシルメチル-3’,4’-エポキシシクロヘキサンカルボキシレート変形されたイプシロン-カプロラクトン
-C:テトラキス(ペンタフルオロフェニルボラート)をアニオンとして有する4級アンモニウム塩(キングインダストリー社、CXC-1821)
-D:アミドカルボキシレート
-WET-270:下記構造のポリエーテル-シロキサン共重合体
-D510:ルーブリゾール社、SolplusTM
Claims (6)
- 有機発光素子の封止材用熱硬化性液状組成物の熱硬化物である有機発光素子の封止材であって、
前記封止材用熱硬化性液状組成物が、
脂肪族四官能エポキシ系化合物と脂環族二官能エポキシ系化合物とを含むバインダー物質;及び
カチオン性熱硬化開始剤;
を含み、
前記脂肪族四官能エポキシ系化合物は、下記の化学式構造を有するペンタエリトリトールグリシジルエーテルであり、
前記カチオン性熱硬化開始剤は、テトラキス(ペンタフルオロフェニルボラート)をアニオンとして有する4級アンモニウム塩であり、
前記バインダー物質の100重量部に対し、前記脂肪族四官能エポキシ系化合物は、60重量部以上で含み、前記脂環族二官能エポキシ系化合物は、40重量部以下で含み、
前記バインダー物質100重量部に対し、前記カチオン性熱硬化開始剤は、2.0~2.5重量部で含み、
前記封止材の光透過率が99.0%以上であり、ヘイズが0.10%以下であることを特徴とする、
有機発光素子の封止材。 - 前記封止材用熱硬化性液状組成物が、界面活性剤をさらに含むことを特徴とする、
請求項1に記載の有機発光素子の封止材。 - 前記界面活性剤は、ポリエーテル-シロキサンの共重合体であることを特徴とする、
請求項2に記載の有機発光素子の封止材。 - 前記封止材用熱硬化性液状組成物が、経時安定剤をさらに含むことを特徴とする、
請求項1に記載の有機発光素子の封止材。 - 前記封止材用熱硬化性液状組成物が、ダムアンドフィル封止(dam and fill encapsulation)用フィル(fill)材料として使用されることを特徴とする、
請求項1に記載の有機発光素子の封止材。 - 前記熱硬化物が、熱硬化によって光学透明樹脂で形成されることを特徴とする、
請求項1に記載の有機発光素子の封止材。
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