WO2013047620A1 - Composition de résine durcissable destinée à sceller un élément semi-conducteur optique, et matériau durci obtenu à partir de celle-ci - Google Patents
Composition de résine durcissable destinée à sceller un élément semi-conducteur optique, et matériau durci obtenu à partir de celle-ci Download PDFInfo
- Publication number
- WO2013047620A1 WO2013047620A1 PCT/JP2012/074789 JP2012074789W WO2013047620A1 WO 2013047620 A1 WO2013047620 A1 WO 2013047620A1 JP 2012074789 W JP2012074789 W JP 2012074789W WO 2013047620 A1 WO2013047620 A1 WO 2013047620A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- epoxy resin
- epoxy
- resin composition
- optical semiconductor
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 59
- 239000004065 semiconductor Substances 0.000 title claims abstract description 49
- 230000003287 optical effect Effects 0.000 title claims abstract description 47
- 238000007789 sealing Methods 0.000 title claims abstract description 24
- 239000000463 material Substances 0.000 title claims abstract description 6
- 239000003822 epoxy resin Substances 0.000 claims abstract description 139
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 139
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 48
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 28
- 238000003860 storage Methods 0.000 claims abstract description 23
- 230000009477 glass transition Effects 0.000 claims abstract description 20
- -1 zinc carboxylate Chemical class 0.000 claims description 124
- 229920002545 silicone oil Polymers 0.000 claims description 53
- 125000003700 epoxy group Chemical group 0.000 claims description 49
- 238000004519 manufacturing process Methods 0.000 claims description 45
- 150000003377 silicon compounds Chemical class 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 239000004593 Epoxy Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims description 15
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000005372 silanol group Chemical group 0.000 claims description 12
- 239000011701 zinc Substances 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 6
- 238000005538 encapsulation Methods 0.000 claims description 6
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims description 3
- IJQXGKBNDNQWAT-UHFFFAOYSA-L zinc;docosanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O IJQXGKBNDNQWAT-UHFFFAOYSA-L 0.000 claims description 3
- 239000000047 product Substances 0.000 description 68
- 150000001875 compounds Chemical class 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 55
- 238000001723 curing Methods 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 230000015572 biosynthetic process Effects 0.000 description 29
- 239000003054 catalyst Substances 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 29
- 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 28
- 239000002904 solvent Substances 0.000 description 28
- 238000005227 gel permeation chromatography Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- 238000012360 testing method Methods 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 150000008065 acid anhydrides Chemical class 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 150000002989 phenols Chemical class 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 239000003566 sealing material Substances 0.000 description 16
- 125000002947 alkylene group Chemical group 0.000 description 14
- 150000001735 carboxylic acids Chemical class 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 11
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 11
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 10
- 150000003138 primary alcohols Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000003158 alcohol group Chemical group 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 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 description 8
- 239000007822 coupling agent Substances 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 238000005486 sulfidation Methods 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- FWHUTKPMCKSUCV-UHFFFAOYSA-N 1,3-dioxo-3a,4,5,6,7,7a-hexahydro-2-benzofuran-5-carboxylic acid Chemical compound C1C(C(=O)O)CCC2C(=O)OC(=O)C12 FWHUTKPMCKSUCV-UHFFFAOYSA-N 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 7
- 239000003463 adsorbent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 150000003333 secondary alcohols Chemical class 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 6
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 5
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 230000006750 UV protection Effects 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- OZEHOHQZIRILDX-UHFFFAOYSA-N ctk1b7797 Chemical compound O=C1OC(=O)C2C1C1(C)CC2CC1 OZEHOHQZIRILDX-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 229920002050 silicone resin Polymers 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 5
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 4
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 4
- LQOPXMZSGSTGMF-UHFFFAOYSA-N 6004-79-1 Chemical compound C1CC2C3C(=O)OC(=O)C3C1C2 LQOPXMZSGSTGMF-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- IIWFPIKUKKAYDT-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-3,4-diol Chemical compound C1CC2(O)C(O)=CC1C2 IIWFPIKUKKAYDT-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 3
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 3
- RGAHHPQKNPTZEY-UHFFFAOYSA-N 2-ethyl-4-methylhexane-1,1-diol Chemical compound CCC(C)CC(CC)C(O)O RGAHHPQKNPTZEY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910052684 Cerium Inorganic materials 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
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- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- RWJUTPORTOUFDY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCOCC1CO1 RWJUTPORTOUFDY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-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
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- DCAFJGSRSBLEPX-UHFFFAOYSA-N tris(2,3-dibutylphenyl) phosphite Chemical compound CCCCC1=CC=CC(OP(OC=2C(=C(CCCC)C=CC=2)CCCC)OC=2C(=C(CCCC)C=CC=2)CCCC)=C1CCCC DCAFJGSRSBLEPX-UHFFFAOYSA-N 0.000 description 1
- OOZKMYBQDPXENQ-UHFFFAOYSA-N tris(2,3-diethylphenyl) phosphite Chemical compound CCC1=CC=CC(OP(OC=2C(=C(CC)C=CC=2)CC)OC=2C(=C(CC)C=CC=2)CC)=C1CC OOZKMYBQDPXENQ-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- QFGXDXGDZKTYFD-UHFFFAOYSA-N tris[2,3-di(propan-2-yl)phenyl] phosphite Chemical compound CC(C)C1=CC=CC(OP(OC=2C(=C(C(C)C)C=CC=2)C(C)C)OC=2C(=C(C(C)C)C=CC=2)C(C)C)=C1C(C)C QFGXDXGDZKTYFD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- JRHDFVNUWLMGBU-UHFFFAOYSA-L zinc octyl phosphate Chemical compound C(CCCCCCC)OP(=O)([O-])[O-].[Zn+2] JRHDFVNUWLMGBU-UHFFFAOYSA-L 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- PORPEXMDRRVVNF-UHFFFAOYSA-L zinc;octadecyl phosphate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCOP([O-])([O-])=O PORPEXMDRRVVNF-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors thereof
-
- 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
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
-
- 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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- H01L23/293—Organic, e.g. plastic
- H01L23/296—Organo-silicon compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Definitions
- the present invention relates to a curable resin composition suitable for optical semiconductor element sealing applications, and a cured product thereof.
- LEDs Light Emitting Diode
- resins that encapsulate optical semiconductor elements are particularly resistant to UV and heat. It has come to be required.
- bisphenol-type epoxy resins and alicyclic epoxy resins have sufficient UV resistance and heat resistance as described above, and may not be used in fields where high luminance is required.
- a silicone resin sealing material using an unsaturated hydrocarbon group-containing organopolysiloxane and an organohydrogenpolysiloxane is used (see Patent Document 2). ).
- a sealing material using such a silicone resin is excellent in UV resistance and heat resistance, it has a problem that the sealing surface becomes sticky or gas permeability is high.
- the problem of high gas permeability is the phenomenon that the silver plating surface used in the LED is corroded due to the permeation of sulfur-based gas, resulting in blackening due to silver sulfide, and reducing the illuminance of the LED. Therefore, the countermeasure is urgent.
- An object of the present invention is to provide a curable resin composition for encapsulating an optical semiconductor element that is extremely excellent in heat cycle resistance.
- the present inventors have found that the cured product has a glass transition temperature (Tg) measured by the DMA method in the range of ⁇ 10 to 10 ° C., and is 0 measured by the DMA method.
- Tg glass transition temperature
- a curable resin composition using an epoxy resin having a specific skeleton that gives a cured product having a storage elastic modulus in the range of 0 to 150 MPa at 0 ° C. solves the above-mentioned problems. It came.
- the optical semiconductor device encapsulated product has a glass transition temperature (Tg) measured by DMA method in the range of ⁇ 10 to 10 ° C. and a storage elastic modulus at 0 ° C. measured in DMA range of 0 to 150 MPa.
- Tg glass transition temperature
- Curable resin composition for stopping (2) The curable resin composition for optical semiconductor element sealing according to (1), comprising an epoxy resin (A) and an epoxy resin curing agent (B), (3) The curable resin composition for optical semiconductor element encapsulation according to (2), wherein the epoxy resin (A) is a silicone skeleton epoxy resin, (4) The silicone skeleton epoxy resin is a polymer of a silanol-terminated silicone oil represented by formula (1) and an epoxy group-containing silicon compound represented by formula (2) obtained through the following production steps 1 and 2, The curable resin composition for sealing an optical semiconductor element according to (3), wherein the epoxy equivalent measured by the method described in JIS K-7236 is 300 to 1500 g / eq, Manufacturing process 1 A step of condensing a silanol group of a silanol-terminated silicone oil and an alkoxy group of an epoxy group-containing silicon compound to obtain a modified silicone oil. Manufacturing process 2 A step of adding water after the production step 1 to hydrolyze and condense the remaining alkoxy groups.
- R 1 represents an alkyl group having 1 to 6 carbon atoms or an aryl group having 5 to 10 carbon atoms, and m represents an average value of 3 to 200. In the formula, a plurality of R 1 are present. They may be the same or different)
- X represents an organic group containing an epoxy group
- R 2 represents a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
- R 3 represents a straight chain having 1 to 10 carbon atoms.
- a chain, branched or cyclic alkyl group, p is an integer from 0 to 2, and r is an integer and represents (3-p).
- the epoxy resin curing agent (B) is a carboxylic acid resin obtained by modifying a carboxylic acid anhydride and / or a carboxylic acid anhydride with an alcoholic hydroxyl group.
- Resin composition (6) Furthermore, as a curing accelerator, zinc carboxylate is contained, (4) or (5) curable resin composition for optical semiconductor element sealing according to (5), (7) The curable resin composition for sealing an optical semiconductor element according to (6), wherein the zinc carboxylate is one or more selected from zinc 2-ethylhexanoate, zinc stearate, zinc behenate, and zinc myristylate, (8) (1) to a cured product obtained by curing the curable resin composition for sealing an optical semiconductor element according to any one of (7), (9) LED comprising the cured product according to (8), About.
- the cured product obtained by curing the curable resin composition of the present invention has a glass transition temperature (Tg) measured by DMA method in the range of ⁇ 10 to 10 ° C., and 0 ° C. measured by DMA method.
- Tg glass transition temperature
- a curable resin composition using an epoxy resin having a specific skeleton, which gives a cured product having a storage elastic modulus in the range of 0 to 150 MPa, is extremely excellent in heat cycle resistance, so that it is encapsulated in an optical semiconductor device (LED) It is extremely useful as a material.
- the curable resin composition for an optical semiconductor element sealing material of the present invention has a glass transition temperature (Tg) measured by the DMA method in the range of ⁇ 10 to 10 ° C., and 0 ° C. measured by the DMA method. Is preferably in the range of 0 to 150 MPa, particularly a glass transition point of ⁇ 5 to 8 ° C. and a storage modulus of 0 to 100 MPa.
- Tg glass transition temperature
- the DMA (Dynamic Mechanical Analysis) method in the present invention is a measurement of dynamic viscoelasticity (tensile vibration) described in JIS K7244 and JIS K7244-4 using the test piece prepared as follows. It is a method to do. ⁇ Method for making DMA test piece> After carrying out the vacuum defoaming for 5 minutes, the optical semiconductor element sealing material is gently cast on a glass substrate on which a dam is created with a heat-resistant tape so as to be 30 mm ⁇ 20 mm ⁇ height 0.8 mm. The casting is cured under predetermined conditions (specifically, conditions of curing at 120 ° C. for 1 hour and then curing at 150 ° C.
- the cured product of the curable resin composition for optical semiconductor encapsulating material of the present invention has a glass transition temperature (Tg) measured by DMA method of ⁇ 10 to 10 ° C., particularly preferably ⁇ 5 to 8 ° C. If it is lower than ⁇ 10 ° C., it may be inferior in sulfidation resistance, and if it is higher than 10 ° C., it may be inferior in heat cycle resistance.
- the cured product of the curable resin composition for an optical semiconductor element sealing material of the present invention has a storage elastic modulus at 0 ° C. measured by the DMA method of 0 to 150 MPa, particularly preferably 0 to 100 MPa. If it exceeds 150 MPa, cracks may occur during the heat cycle test.
- the heat cycle test (also referred to as a thermal shock test or a heat shock test) is a test piece in a low temperature region of about ⁇ 50 to ⁇ 30 ° C. and a high temperature region of about 80 to 120 ° C. for about 5 to 30 minutes in each region. Is repeatedly used, and is widely used as a reliability confirmation test for optical semiconductor encapsulants.
- the curable resin composition of the present invention is a curable resin composition for sealing an optical semiconductor element, and the cured product has a glass transition temperature (Tg) measured by DMA method of ⁇ 10 to 10 ° C., The storage elastic modulus at 0 ° C. measured by the DMA method is 0 to 150 MPa.
- the curable resin composition include a silicone resin composition and an epoxy resin composition.
- the curable resin composition of the present invention is preferably a curable resin composition (epoxy resin composition) containing an epoxy resin (A) from the viewpoint of resistance to sulfide.
- the epoxy resin (A) of this invention is demonstrated.
- the epoxy resin (A) is a compound having two or more epoxy groups in the same molecule, such as a silicone skeleton epoxy resin, an epoxy resin that is a glycidyl etherified product of a phenol compound, and a glycidyl etherified product of various novolac resins.
- epoxy resins cycloaliphatic epoxy resins, aliphatic epoxy resins, heterocyclic epoxy resins, glycidyl ester epoxy resins, glycidyl amine epoxy resins, epoxy resins obtained by glycidylation of halogenated phenols, polymerization with epoxy groups
- a copolymer of a polymerizable unsaturated compound and another polymerizable unsaturated compound, and the like, and a silicone skeleton epoxy resin is preferable because of its heat resistance and light resistance.
- the silicone skeleton epoxy resin is a resin having an epoxy group having a silicone bond (Si—O bond) as a main skeleton, and can be obtained, for example, by polymerizing an epoxy group-containing silicon compound and other silicon compounds.
- examples thereof include a hydrolytic condensation polymer of an alkoxysilane compound having an epoxy group and an alkoxysilane having a methyl group or a phenyl group, and a condensation polymer of an alkoxysilane compound having an epoxy group and a silanol-terminated silicone oil.
- an addition polymerization product of a silicone resin having a hydrosilyl group (SiH group) and an epoxy compound having an unsaturated hydrocarbon group such as a vinyl group can be exemplified.
- the epoxy resin (A) in the present invention is made from a silanol-terminated silicone oil (a) and an epoxy group-containing silicon compound (b) (and, if necessary, an alkoxysilicon compound (c)) among the silicone skeleton epoxy resins.
- a silicone skeleton epoxy resin obtained through a two-stage production process described later is most preferable.
- silanol-terminated silicone oil (a), the epoxy group-containing silicon compound (b), and the alkoxysilicon compound (c) will be described.
- silanol-terminated silicone oil (a) examples include a silicone resin represented by the following formula (1) and having silanol groups at both ends.
- R 1 represents an alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or a hexyl group, or a carbon number of 5 to 5 such as a phenyl group, a benzyl group or a naphthyl group. 10 aryl groups are shown.
- a plurality of R 1 may be the same or different, but preferably contain a phenyl group from the viewpoint of compatibility with other resins, high refractive index, and improvement in sulfur resistance. From the viewpoint of reducing the glass transition temperature of the cured product and the storage elastic modulus at 0 ° C., it preferably contains a methyl group.
- the proportion of the phenyl group contained is preferably 0.05 to 2.0 mol, more preferably 0.1 to 1.0 mol, and still more preferably 0.15 to 0.3 mol, per 1 mol of the substituted methyl group. Particularly preferred is 0.15 to 0.2 mol. If the amount is less than 0.05 mol, the compatibility with other raw materials in the composition may decrease, the refractive index of the cured product may decrease, the light extraction efficiency of the LED may decrease, and the sulfidation resistance may decrease. When the amount exceeds 2.0 mol, the light resistance (UV resistance) of the cured product may decrease, the storage elastic modulus at 0 ° C. in the DMA method may increase excessively, or the heat cycle resistance may decrease. .
- m represents an average value of 3 to 200, preferably 3 to 100, more preferably 3 to 50.
- m represents an average value of 3 to 200, preferably 3 to 100, more preferably 3 to 50.
- the weight average molecular weight (Mw) of the silanol-terminated silicone oil (a) is preferably in the range of 400 to 3000 (GPC). If the weight average molecular weight is less than 400, the silicone part is less likely to exhibit the characteristics of heat resistance and light resistance, and if it exceeds 3000, it has a severe layer separation structure, so that it can be used for optical semiconductor element sealing. May be less permeable.
- the molecular weight of the silanol-terminated silicone oil (a) is a weight average molecular weight (Mw) calculated in terms of polystyrene based on a value measured under the following conditions using GPC (gel permeation chromatography). means.
- Silanol-terminated silicone oil (a) is produced, for example, by hydrolyzing and condensing dimethyl dialkoxysilane, methylphenyldichlorosilane, diphenylalkoxysilane, dimethyldichlorosilane, methylphenyldichlorosilane, diphenyldichlorosilane. it can.
- preferable silanol-terminated silicone oil (a) include the following product names.
- PRX413, BY16-873 manufactured by Toray Dow Corning Co., Ltd. X-21-5841, KF-9701 manufactured by Shin-Etsu Chemical Co., Ltd., XC96-723, TSR160, YR3370, YF3800, manufactured by Momentive Co., Ltd.
- the epoxy group-containing silicon compound (b) in the present invention is an alkoxy silicon compound represented by the formula (2).
- X is not particularly limited as long as X is an organic group having an epoxy group.
- an alkyl group having 1 to 4 carbon atoms substituted with a glycidoxy group such as ⁇ -glycidoxyethyl, ⁇ -glycidoxypropyl, ⁇ -glycidoxybutyl, glycidyl group, ⁇ - (3,4-epoxy Cyclohexyl) ethyl group, ⁇ - (3,4-epoxycyclohexyl) propyl group, ⁇ - (3,4-epoxycycloheptyl) ethyl group, 4- (3,4-epoxycyclohexyl) butyl group, 5- (3 And an alkyl group having 1 to 5 carbon atoms substituted with a cycloalkyl group having 5 to 8 carbon atoms having an oxirane group such as 4-epoxycyclohexyl) pentyl group.
- a glycidoxy group such as
- alkyl group having 1 to 3 carbon atoms substituted with a glycidoxy group and an alkyl group having 1 to 3 carbon atoms substituted with a cycloalkyl group having 5 to 8 carbon atoms having an epoxy group for example, ⁇ -Glycidoxyethyl group, ⁇ -glycidoxypropyl group, ⁇ - (3,4-epoxycyclohexyl) ethyl group are preferable, and since ⁇ - (3,4-epoxycyclohexyl) ethyl group can be particularly suppressed in coloration Is preferred.
- R 2 in the formula (2) represents a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 3 carbon atoms such as a methyl group, a cyclohexyl group, etc. And an alkyl group having 5 to 8 carbon atoms having an alicyclic structure and an alkyl group having 5 to 8 carbon atoms having an aromatic ring structure such as a phenyl group.
- R 3 in the formula (2) represents a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms.
- R 3 is preferably a methyl group or an ethyl group, and particularly preferably a methyl group, from the viewpoint of reaction conditions such as compatibility and reactivity.
- p is an integer representing 0, 1, 2 and r represents (3-p). From the viewpoint of the viscosity of the silicone skeleton epoxy resin and the mechanical strength of the cured product, p is preferably 0 or 1.
- epoxy group-containing silicon compound (b) examples include ⁇ -glycidoxyethyltrimethoxysilane, ⁇ -glycidoxyethyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, and ⁇ -glycidoxy.
- an alkoxysilicon compound (c) represented by the following formula (3) can be used in combination with the epoxy group-containing silicon compound (b).
- the viscosity, refractive index, Tg in the DMA method of the cured product, and storage elastic modulus of the silicone skeleton epoxy resin can be adjusted.
- R 2 , R 3 , p and r in the formula (3) have the same contents as described above.
- Preferred examples of the alkoxysilicon compound (c) that can be used in combination include methyltrimethoxysilane, phenyltrimethoxysilane, cyclohexyltrimethoxysilane, methyltriethoxysilane, phenyltriethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, and diphenyl. Examples include dimethoxysilane and diphenyldidiethoxysilane. Among these, methyltrimethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, and diphenyldimethoxysilane are preferable.
- At least one of the silanol-terminated silicone oil (a) and the epoxy group-containing silicon compound (b) (and optionally the alkoxysilicon compound (c)) to be used has an aromatic skeleton. It is preferable to use a compound having a phenyl group from the viewpoint of an increase in refractive index and a reduction in sulfur resistance, and a compound having a phenyl group is particularly preferable.
- the silanol-terminated silicone oil (a) preferably has a phenyl group.
- silanol-terminated silicone oil (a) introduced with a phenyl group can suppress an excessive increase in viscosity of the silicone skeleton epoxy resin, while an epoxy group-containing silicon compound with a phenyl group (b) ) (And if necessary, the alkoxysilicon compound (c)), the increase in viscosity becomes large and workability may be inferior.
- the alkoxy group-containing silicon compound (b) (and, if necessary, the alkoxy group of the alkoxysilicon compound (c)) is added to 1 equivalent of the silanol group of the silanol-terminated silicone oil (a).
- the alkoxy group-containing silicon compound (b) (and, if necessary, the alkoxy group of the alkoxysilicon compound (c)) is added to 1 equivalent of the silanol group of the silanol-terminated silicone oil (a).
- two or more alkoxy groups in the epoxy group-containing silicon compound (b) (and optionally the alkoxysilicon compound (c)) are terminated with silanol-terminated silicone oil (a )
- the silanol group the polymer becomes too high at the end of the production step 1 and gelation may occur.
- (Manufacturing process 1) A step of obtaining a modified silicone oil (d) by condensing a silanol group of a silanol-terminated silicone oil (a) and an alkoxy group of an epoxy group-containing silicon compound (b) (and, if necessary, an alkoxysilicon compound (c)). .
- (Manufacturing process 2) A step of adding water after the production step 1 to hydrolyze and condense the remaining alkoxy groups. Through the production steps 1 and 2, the silanol-terminated silicone oil (a) and the epoxy group-containing silicon compound (b) (and the alkoxysilicon compound (c) as necessary) are polymerized.
- the silanol group of the silanol-terminated silicone oil (a) and the alkoxy group of the epoxy group-containing silicon compound (b) (and the alkoxy silicon compound (c) if necessary) are surely obtained.
- the modified silicone oil (d) is obtained by reacting with the above, it is possible to obtain a uniform and stable product by subjecting the remaining alkoxy groups to dealcoholic hydrolysis and condensation.
- the condensation reaction between the silanol group and the alkoxy group and the polymerization reaction between the alkoxysilanes become a competitive reaction, resulting in a difference in the reaction rate between the products and the compatibility of the products. Due to the difference, a heterogeneous compound can be obtained, or a large amount of silanol-terminated silicone oil (a) having no epoxy group can be adversely affected.
- the reaction is preferably performed in the presence of a solvent, and alcohol is particularly preferable among the solvents from the viewpoint of reaction control.
- alcohols that can be used include alcohols having 1 to 10 carbon atoms, such as methanol, ethanol, propanol, isopropanol, butanol, t-butanol, hexanol, octanol, nonane alcohol, decane alcohol, cyclohexanol, and cyclopentanol. Etc.
- primary alcohols and secondary alcohols are preferable, and it is particularly preferable to use primary alcohols or a mixture of primary alcohols and secondary alcohols.
- Examples of primary alcohols include methanol, ethanol, propanol, butanol, hexanol, octanol, nonane alcohol, decane alcohol, propylene glycol, and the like.
- Examples of secondary alcohols include isopropanol, cyclohexanol, propylene glycol. Etc.
- a low molecular weight alcohol having 1 to 4 carbon atoms such as methanol, ethanol, propanol, isopropanol, butanol and t-butanol is preferred. These alcohols may be used as a mixture.
- the amount of primary alcohol is preferably 5% by weight or more, more preferably 10% by weight or more of the total alcohol amount.
- the amount of alcohol used is 2% by weight or more based on the total weight of the silanol-terminated silicone oil (a) and the epoxy group-containing silicon compound (b) (and, if necessary, the alkoxysilicon compound (c)). It is preferable to contain. It is more preferably 2 to 100% by weight, further preferably 3 to 50% by weight, particularly preferably 4 to 40% by weight. When the amount exceeds 100% by weight, the progress of the reaction becomes extremely slow. When the amount is less than 2% by weight, the reaction other than the target reaction proceeds, the molecular weight increases, gelation, increase in viscosity, and use as a cured product.
- solvents may be used in combination as necessary.
- solvents that can be used in combination include ketones such as methyl ethyl ketone, methyl isobutyl ketone, and cyclopentanone, esters such as ethyl acetate, butyl acetate, ethyl lactate, and isopropyl butanoate, hydrocarbons such as hexane, cyclohexane, toluene, and xylene. Can be illustrated.
- the reaction in the production process 1 can be carried out without a catalyst, the reaction proceeds slowly with no catalyst, so that it is preferably carried out in the presence of a catalyst from the viewpoint of shortening the reaction time.
- the catalyst that can be used any compound that exhibits acidity or basicity can be used.
- the acidic catalyst include inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, and organic acids such as formic acid, acetic acid and oxalic acid.
- Examples of basic catalysts include sodium hydroxide, potassium hydroxide, lithium hydroxide, alkali metal hydroxides such as cesium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc.
- Inorganic bases such as alkali metal carbonates and organic bases such as ammonia, triethylamine, diethylenetriamine, n-butylamine, dimethylaminoethanol, triethanolamine, and tetramethylammonium hydroxide can be used.
- a basic catalyst is particularly preferable, and an inorganic base is preferable in terms of easy catalyst removal from the product.
- alkali metal salts such as sodium hydroxide, potassium hydroxide and calcium hydroxide, or alkaline earth metal salts, particularly hydroxides are preferable.
- the amount of the catalyst added is usually 0.001 to 5% by weight based on the total weight of the silanol-terminated silicone oil (a) and the epoxy group-containing silicon compound (b) (and the alkoxysilicon compound (c) if necessary). Preferably, it is 0.01 to 2% by weight.
- a method for adding the catalyst it is added directly or used in a state dissolved in a soluble solvent or the like. Among them, it is preferable to add the catalyst in a state in which the catalyst is dissolved in advance in alcohols such as methanol, ethanol, propanol and butanol.
- the reaction product produced thereby may not be compatible with the silanol-terminated silicone oil (a) and may become cloudy.
- the allowable range of moisture is preferably 0.5% by weight based on the total weight of the silanol-terminated silicone oil (a) and the epoxy group-containing silicon compound (b) (and, if necessary, the alkoxysilicon compound (c)). % Or less, more preferably 0.3% by weight or less, and it is more preferable that there is as little water as possible.
- the reaction temperature in the production step 1 is usually 20 to 160 ° C., preferably 40 to 100 ° C., particularly preferably 50 to 95 ° C., although it depends on the amount of catalyst and the solvent used.
- the reaction time is usually 1 to 20 hours, preferably 3 to 12 hours.
- the modified silicone oil (d) obtained by the manufacturing process 1 has a structure as shown in the following formula (4) as a main component (it is difficult to confirm the structure and accurately Cannot be identified.)
- R 1 and m have the same meaning as described above.
- R 4 represents X and / or R 2 described above, and R 5 represents R 2 and / or —OR 3 .
- the manufacturing process 2 After completion of the reaction in the production step 1, water is added, and the alkoxy groups remaining in the resulting modified silicone oil (d) are polymerized (sol-gel reaction). At this time, the silicon compound (b) containing the above-described epoxy group (and the alkoxysilicon compound (c) if necessary) and the catalyst may be added within the above-mentioned amount as necessary. This reaction is performed between (1) the modified silicone oils (d) and / or (2) the silicon compound (b) containing an epoxy group (and the alkoxysilicon compound (c) if used).
- the polymerization reactions (1) to (4) are considered to proceed simultaneously in parallel.
- a basic inorganic catalyst is preferable as the catalyst, and a necessary amount may be added in the production process 1 in advance. However, it is not preferable to exceed the range described as a preferred embodiment in the production process 1.
- alcohol is preferably used as the solvent in the production process 2.
- examples of alcohols that can be used include alcohols having 1 to 10 carbon atoms, such as methanol, ethanol, propanol, isopropanol, butanol, t-butanol, hexanol, octanol, nonane alcohol, decane alcohol, cyclohexanol, and cyclopentanol. Etc.
- primary alcohols and secondary alcohols are particularly preferred, and primary alcohols are particularly preferred.
- a low molecular weight alcohol having 1 to 4 carbon atoms such as methanol, ethanol, propanol, isopropanol, butanol and t-butanol is preferred. These alcohols may be used as a mixture. The presence of these alcohols contributes to molecular weight control and stability.
- the silanol-terminated silicone oil (a) and the silicon compound (b) containing an epoxy group (and, if necessary, the alkoxysilicon compound (c)) charged in the production process 1 as the addition amount of the alcohol, Usually 20 to 200% by weight, preferably 20 to 150% by weight, particularly preferably 30 to 120% by weight.
- water is added (ion exchange water, distilled water, or clean water can be used).
- the amount of water used is preferably 0.5 to 8.0 equivalents, more preferably 0.6 to 5.0 equivalents, particularly preferably 0.65 to 2.0 equivalents relative to the amount of remaining alkoxy groups. is there.
- the amount of water is less than 0.5 equivalent, the progress of the reaction is slow and the silicon compound (b) containing an epoxy group (and the alkoxysilicon compound (c) if necessary) remains without reacting.
- a problem such as the above will occur, a sufficient network may not be formed, and a curing failure will occur even after the subsequent curing of the curable resin composition.
- the molecular weight control is not effective, and the molecular weight may be higher than necessary. Furthermore, there is a possibility of inhibiting the stability of the silicone skeleton epoxy resin.
- the reaction temperature in production step 2 is usually 20 to 160 ° C., preferably 40 to 100 ° C., particularly preferably 50 to 95 ° C., although it depends on the amount of catalyst and the solvent used.
- the reaction time is usually 1 to 20 hours, preferably 3 to 12 hours.
- the catalyst is removed by quenching and / or washing with water as necessary.
- a solvent that can be separated from water.
- Preferred solvents include ketones such as methyl ethyl ketone, methyl isobutyl ketone and cyclopentanone, esters such as ethyl acetate, butyl acetate, ethyl lactate and isopropyl butanoate, hydrocarbons such as hexane, cyclohexane, toluene and xylene. Can be illustrated.
- the catalyst may be removed only by washing with water, but the reaction is carried out under acidic or basic conditions. It is preferable to remove the adsorbent by filtration after adsorbing the catalyst using Any compound that is acidic or basic can be used for the neutralization reaction.
- the compound exhibiting acidity include inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, and organic acids such as formic acid, acetic acid and oxalic acid.
- Examples of compounds showing basicity include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide and cesium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
- Inorganic bases such as alkali metal carbonates, phosphoric acid, sodium dihydrogen phosphate, disodium hydrogen phosphate, trisodium phosphate, phosphates such as polyphosphoric acid, sodium tripolyphosphate, ammonia, triethylamine, diethylenetriamine, n-butylamine, Organic bases such as dimethylaminoethanol, triethanolamine, and tetramethylammonium hydroxide can be used.
- an inorganic base or an inorganic acid is particularly preferable because it can be easily removed from the product, and phosphates that can more easily adjust the pH to near neutral are more preferable.
- adsorbent examples include activated clay, activated carbon, zeolite, inorganic / organic synthetic adsorbent, ion exchange resin, and the like, and specific examples include the following products.
- activated clay for example, Toshin Kasei Co., Ltd., activated clay SA35, SA1, T, R-15, E, Nikkanite G-36, G-153, G-168 are manufactured by Mizusawa Chemical Co., Ltd. Galeon Earth, Mizuka Ace, etc. are listed.
- activated carbon for example, CL-H, Y-10S, Y-10SF manufactured by Ajinomoto Fine Techno Co., Ltd., S, Y, FC, DP, SA1000, K, A, KA, M, CW130BR manufactured by Phutamura Chemical Co., Ltd. , CW130AR, GM130A, and the like.
- zeolite include, for example, molecular sieves 3A, 4A, 5A, and 13X, manufactured by Union Showa.
- a synthetic adsorbent for example, Kyoward 100, 200, 300, 400, 500, 600, 700, 1000, 2000 manufactured by Kyowa Chemical Co., Ltd., Amberlist 15JWET, 15DRY, manufactured by Rohm and Haas Co., Ltd. 16WET, 31WET, A21, Amberlite IRA400JCl, IRA403BLCl, IRA404JCl, manufactured by Dow Chemical Company, Dowex 66, HCR-S, HCR-W2, MAC-3, etc. may be mentioned.
- the adsorbent is added to the reaction solution, followed by treatment such as stirring and heating to adsorb the catalyst, and then the adsorbent is filtered and the residue is washed with water to remove the catalyst and adsorbent.
- the reaction After completion of the reaction or after quenching, it can be purified by conventional separation and purification means other than water washing and filtration.
- the purification means include column chromatography, vacuum concentration, distillation, extraction and the like. These purification means may be performed singly or in combination.
- reaction solvent mixed with water is removed from the system by distillation or vacuum concentration after quenching, and then washed with a solvent that can be separated from water. It is preferable.
- the silicone skeleton epoxy resin of the present invention can be obtained by removing the solvent by vacuum concentration or the like.
- the appearance of the silicone skeleton epoxy resin of the present invention is usually colorless and transparent and is a liquid having fluidity at 25 ° C.
- the molecular weight is preferably 800 to 3000, more preferably 1000 to 3000, and particularly preferably 1500 to 2800 as the weight average molecular weight measured by GPC. When the weight average molecular weight is less than 800, the heat resistance may be lowered. When the weight average molecular weight is more than 3000, the encapsulant may be peeled off from the substrate at the time of solder reflow of the LED element encapsulated using the weight average molecular weight.
- the weight average molecular weight is a polystyrene equivalent weight average molecular weight (Mw) measured using GPC (gel permeation chromatography) under the following conditions.
- the epoxy equivalent (measured by the method described in JIS K-7236) of the silicone skeleton epoxy resin of the present invention is 300 to 1500 g / eq.
- the silicone skeleton epoxy resin of the present invention may be a single silicone skeleton epoxy resin or a mixture of two or more silicone skeleton epoxy resins.
- the epoxy equivalent of the epoxy resin is a single silicone skeleton epoxy resin, two or more types of silicone skeleton epoxy resins are used.
- the total epoxy equivalent of the epoxy equivalent of the specific silicone skeleton epoxy resin ⁇ (content of the specific silicone skeleton epoxy resin / total amount of the silicone skeleton epoxy resin) is 300 to 1500 g / eq. It is preferably 350 to 1000 g / eq.
- the viscosity of the silicone skeleton epoxy resin of the present invention is preferably 50 to 20,000 mPa ⁇ s, more preferably 500 to 10,000 mPa ⁇ s, particularly 800 to 5 1,000 mPa ⁇ s is preferred.
- the viscosity is less than 50 mPa ⁇ s, the viscosity is too low and may not be suitable as an optical semiconductor sealing material.
- it exceeds 20,000 mPa ⁇ s the viscosity is too high and workability is reduced. There is.
- the ratio of silicon atoms to which three oxygen atoms are bonded to the total silicon atoms is preferably 3 to 50 mol%, more preferably 5 to 30 mol%, and particularly preferably 6 to 15 mol%. preferable.
- the ratio of silicon atoms bonded to three oxygen atoms derived from silsesquioxane with respect to all silicon atoms is less than 3 mol%, the cured product tends to be too soft as a characteristic of the chain silicone segment, and the surface Tack and scratches may occur.
- it exceeds 50 mol% the properties of the silicone oil are liable to be impaired, and the cured product becomes too hard.
- the proportion of silicon atoms present can be determined by 1 H NMR, 29 Si NMR, elemental analysis, etc. of the epoxy resin.
- the epoxy resin (A) in the present invention a silicon compound containing a silanol-terminated silicone oil (a) and an epoxy group, which is a silicone skeleton epoxy resin, obtained through production steps 1 and 2 ( b) (and condensates with alkoxysilicon compounds (c) if necessary) have been described.
- the above silanol-terminated silicone oil (a) is not used, but a condensation polymer of a silicon compound (b) containing an epoxy group (and an alkoxy silicon compound (c) if necessary), Can also be illustrated.
- the silicon compound (b) containing an epoxy group represented by the above formula (2) (and optionally represented by the above formula (3) can be produced by a one-step reaction.
- the alkoxysilicon compound (c)) can be obtained by adding water dropwise in the presence of a catalyst and a solvent as described above and condensing under the conditions of a reaction temperature of 40 to 100 ° C. and a reaction time of 1 to 24 hours.
- a condensate of the silicon compound (b) containing an epoxy group (and, if necessary, the alkoxysilicon compound (c)) can be obtained by quenching, removing, washing with water, and concentrating as described above. .
- An embodiment of the silicone skeleton epoxy resin that is particularly preferable from the viewpoint that the glass transition temperature and the storage elastic modulus at 0 ° C. of the present invention satisfy the required characteristics and has excellent sulfidation resistance is as follows.
- (Iii) The silicone skeleton epoxy resin according to any one of (i) and (ii), wherein a ratio of silicon atoms to which three oxygen atoms are bonded to all silicon atoms is 3 to 50 mol%.
- (Iv) The silicone skeleton epoxy resin according to any one of (i) and (ii), wherein a ratio of silicon atoms to which three oxygen atoms are bonded to all silicon atoms is 6 to 15 mol%.
- (V) The silicone skeleton epoxy resin according to any one of (i) to (iv), wherein an epoxy equivalent is 350 to 1000 g / eq.
- the epoxy equivalent of the specific silicone skeleton epoxy resin ⁇ (the content of the specific silicone skeleton epoxy resin / the total amount of the silicone skeleton epoxy resin)
- the silicone skeleton epoxy resin mixture according to any one of (i) to (iv), wherein an epoxy equivalent is 350 to 1000 g / eq.
- epoxy resins include epoxy resins that are glycidyl etherification products of phenolic compounds, epoxy resins that are glycidyl etherification products of various novolak resins, alicyclic epoxy resins, aliphatic epoxy resins, heterocyclic epoxy resins, glycidyl esters.
- Examples of the epoxy resin that is a glycidyl etherified product of the phenol compound include 2- [4- (2,3-epoxypropoxy) phenyl] -2- [4- [1,1-bis [4- (2,3 -Hydroxy) phenyl] ethyl] phenyl] propane, bisphenol A, bisphenol F, bisphenol S, 4,4'-biphenol, tetramethyl bisphenol A, dimethyl bisphenol A, tetramethyl bisphenol F, dimethyl bisphenol F, tetramethyl bisphenol S, Dimethylbisphenol S, tetramethyl-4,4′-biphenol, dimethyl-4,4′-biphenol, 1- (4-hydroxyphenyl) -2- [4- (1,1-bis- (4-hydroxyphenyl) Ethyl) phenyl] propane, 2,2'-methylene -Bis (4-methyl-6-tert-butylphenol), 4,4'-butylidene-bis (3-methyl-6
- epoxy resins that are glycidyl etherified products of various novolak resins include phenols, cresols, ethylphenols, butylphenols, octylphenols, bisphenols such as bisphenol A, bisphenol F and bisphenol S, and naphthols.
- examples include novolak resins made from various phenols, xylylene skeleton-containing phenol novolak resins, dicyclopentadiene skeleton-containing phenol novolak resins, biphenyl skeleton-containing phenol novolak resins, fluorene skeleton-containing phenol novolak resins, and other glycidyl etherified products. It is done.
- Examples of the alicyclic epoxy resin include alicyclic rings having an aliphatic ring skeleton such as 3,4-epoxycyclohexylmethyl- (3,4-epoxy) cyclohexylcarboxylate and bis (3,4-epoxycyclohexylmethyl) adipate. And a formula epoxy resin.
- Examples of the aliphatic epoxy resin include glycidyl ethers of polyhydric alcohols such as 1,4-butanediol, 1,6-hexanediol, polyethylene glycol, and pentaerythritol.
- heterocyclic epoxy resin examples include heterocyclic epoxy resins having a heterocyclic ring such as an isocyanuric ring and a hydantoin ring.
- examples of the glycidyl ester-based epoxy resin include epoxy resins made of carboxylic acid esters such as hexahydrophthalic acid diglycidyl ester.
- examples of the glycidylamine-based epoxy resin include epoxy resins obtained by glycidylating amines such as aniline and toluidine.
- epoxy resins obtained by glycidylating halogenated phenols include brominated bisphenol A, brominated bisphenol F, brominated bisphenol S, brominated phenol novolac, brominated cresol novolac, chlorinated bisphenol S, chlorinated bisphenol A, and the like.
- An epoxy resin obtained by glycidylating any of the halogenated phenols include brominated bisphenol A, brominated bisphenol F, brominated bisphenol S, brominated phenol novolac, brominated cresol novolac, chlorinated bisphenol S, chlorinated bisphenol A, and the like.
- Marproof G-0115S, G-0130S and G-0250S are commercially available products.
- the polymerizable unsaturated compound having an epoxy group include glycidyl acrylate, glycidyl methacrylate, 4 -Vinyl-1-cyclohexene-1,2-epoxide and the like.
- Examples of other polymerizable unsaturated compounds include methyl (meth) acrylate, ether (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, styrene, vinylcyclohexane and the like.
- the aforementioned epoxy resin (A) may be used alone or in combination of two or more.
- a silicone skeleton epoxy resin is the most preferable example from the viewpoints of transparency, heat-resistant transparency, light-resistant transparency, heat cycle resistance, and the like.
- an alicyclic epoxy is used.
- the combined use of the resin is preferable from the viewpoint of adjusting the mechanical strength of the cured product.
- an alicyclic epoxy resin a compound having an epoxycyclohexane structure in the skeleton is preferable, and an epoxy resin obtained by an oxidation reaction of a compound having a cyclohexene structure is particularly preferable.
- epoxy resins include esterification reaction of cyclohexene carboxylic acid and alcohols or esterification reaction of cyclohexene methanol and carboxylic acids (Tetrahedron vol.36 p.2409 (1980), Tetrahedron Letter p.4475 (1980), etc.) Described), or Tyschenko reaction of cyclohexene aldehyde (method described in Japanese Patent Application Laid-Open No. 2003-170059, Japanese Patent Application Laid-Open No.
- the alcohol is not particularly limited as long as it is a compound having an alcoholic hydroxyl group, but ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,4-butanediol, 1,5- Pentanediol, 1,6-hexanediol, cyclohexanedimethanol, 2,4-diethylpentanediol, 2-ethyl-2-butyl-1,3-propanediol, neopentyl glycol, tricyclodecane dimethanol, norbornenediol, etc.
- Diols Diols, glycerol, trimethylolethane, trimethylolpropane, trimethylolbutane, triols such as 2-hydroxymethyl-1,4-butanediol, and tetraols such as pentaerythritol and ditrimethylolpropane.
- carboxylic acids include, but are not limited to, oxalic acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid, adipic acid, and cyclohexanedicarboxylic acid.
- epoxy resins include ERL-4221, UVR-6105, ERL-4299 (all trade names, all manufactured by Dow Chemical), Celoxide 2021P, Epolide GT401, EHPE3150, EHPE3150CE (all trade names, all Daicel) (Chemical Industry) and dicyclopentadiene diepoxide, and the like, but are not limited to them (reference: review epoxy resin basic edition I p76-85, the entire contents of which are incorporated herein by reference).
- the ratio of the silicone skeleton epoxy resin to the total epoxy resin composition is preferably 60 to 99 parts by weight, particularly 90 to 97 parts by weight. preferable. If it is less than 60 parts by weight, the light resistance (UV resistance) of the cured product may be inferior.
- epoxy resin curing agent (B) examples include amine compounds, acid anhydride compounds, amide compounds, phenol compounds, and polycarboxylic acids.
- acid anhydride (Ba) and polyvalent carboxylic acid (Bb) are particularly preferable from the viewpoints of hardness, workability (being liquid at room temperature), and transparency of the cured product. preferable.
- the acid anhydride (Ba) include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl nadic anhydride, nadic anhydride, Hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, butanetetracarboxylic anhydride, bicyclo [2,2,1] heptane-2,3-dicarboxylic anhydride, methylbicyclo [2,2,1] heptane-2 , 3-dicarboxylic acid anhydride, cyclohexane-1,3,4-tricarboxylic acid-3,4-anhydride, and the like.
- methyltetrahydrophthalic anhydride methylnadic anhydride, nadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, butanetetracarboxylic anhydride, bicyclo [2,2,1] heptane-2,3-dicarboxylic acid Acid anhydride, methylbicyclo [2,2,1] heptane-2,3-dicarboxylic acid anhydride, cyclohexane-1,3,4-tricarboxylic acid-3,4-anhydride, It is preferable from the viewpoint of workability.
- the polyvalent carboxylic acid (Bb) is a compound having at least two carboxyl groups.
- the polyvalent carboxylic acid (Bb) is preferably a bi- to hexafunctional carboxylic acid, such as butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, Linear alkyl diacids such as malic acid, alkyltricarboxylic acids such as 1,3,5-pentanetricarboxylic acid, citric acid, phthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid , Cycloaliphatic tricarboxylic acid, nadic acid, aliphatic cyclic polyvalent carboxylic acid such
- the polyhydric carboxylic acid whose said acid anhydride is a saturated aliphatic cyclic acid anhydride is preferable from a transparency viewpoint.
- the bi- to hexafunctional polyhydric alcohol is not particularly limited as long as it is a compound having an alcoholic hydroxyl group, but ethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,4-butanediol.
- Diols such as methanol and norbornene diol
- triols such as glycerin, trimethylol ethane, trimethylol propane, tri
- Preferred polyhydric alcohols are alcohols having 5 or more carbon atoms, such as 1,6-hexanediol, 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, 1,2-cyclohexanedimethanol, 2,4 Compounds such as diethylpentanediol, 2-ethyl-2-butyl-1,3-propanediol, neopentyl glycol, tricyclodecane dimethanol, norbornene diol are preferred, and 2-ethyl-2-butyl-1,3 is particularly preferred Alcohols having a branched chain structure or a cyclic structure such as propanediol, neopentyl glycol, 2,4-diethylpentanediol, 1,4-cyclohexanedimethanol, tricyclodecane dimethanol, norbornenediol, From the viewpoint of transparency, In particular, tricyclodecane
- Examples of acid anhydrides to be reacted with polyhydric alcohols include methyltetrahydrophthalic anhydride, methylnadic anhydride, nadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, butanetetracarboxylic anhydride, bicyclo [2, 2,1] heptane-2,3-dicarboxylic acid anhydride, methylbicyclo [2,2,1] heptane-2,3-dicarboxylic acid anhydride, cyclohexane-1,3,4-tricarboxylic acid-3,4- Anhydrides and the like are preferable, and methylhexahydrophthalic anhydride and cyclohexane-1,3,4-tricarboxylic acid-3,4-anhydride are particularly preferable from the viewpoints of heat resistance, transparency, and workability.
- the conditions for the addition reaction can be used without any particular limitation as long as they are known methods.
- Specific reaction conditions include, for example, acid anhydrides and polyhydric alcohols in the absence of a catalyst and in the absence of a solvent.
- a method of reacting at 150 ° C. and heating, and taking out as it is after completion of the reaction can be mentioned.
- both terminal carbinol-modified silicone oil (e) (and, if necessary, terminal alcohol polyester (f)) and one or more carboxylic anhydride groups in the molecule.
- a polyvalent carboxylic acid (Bb) produced by a reaction with the compound (g) having the above can also be used.
- both-end carbinol-modified silicone oil (e) the following formula (5)
- R 6 represents an alkyl group having 1 to 6 carbon atoms or an aryl group having 5 to 10 carbon atoms
- R 7 represents an alkylene group having 1 to 10 carbon atoms in total, an alkylene group having an ether bond
- n Represents an average value of 1 to 100.
- R 6 examples include a methyl group, an ethyl group, an isopropyl group, a butyl group, a hexyl group, a cyclohexyl group, a phenyl group, a benzyl group, and a naphthyl group.
- the polyvalent carboxylic acid (Bb) obtained by the addition reaction of the both-end carbinol-modified silicone oil (e) and the compound (g) having one or more carboxylic anhydride groups in the molecule is liquid at room temperature.
- a methyl group is preferred.
- R 7 examples include methylene, ethylene, propylene, isopropylene, butylene, isobutylene, pentylene, isopentylene, hexylene, heptylene, octylene and other alkylene groups, ethoxyethylene group, propoxyethylene group,
- Examples include an alkylene group having an ether bond such as a propoxypropylene group and an ethoxypropylene group. Particularly preferred are propoxyethylene group and ethoxypropylene group.
- n is an average value of 1 to 100, preferably 2 to 80, more preferably 5 to 30.
- the both-end carbinol-modified silicone oil (e) represented by the formula (5) is, for example, X-22-160AS, KF6001, KF6002, KF6003 (all manufactured by Shin-Etsu Chemical Co., Ltd.) BY16-201, BY16-004.
- SF8427 both manufactured by Toray Dow Corning Co., Ltd.
- XF42-B0970, XF42-C3294 both manufactured by Momentive Performance Materials Japan GK
- These two terminal carbinol-modified silicone oils can be used alone or in combination.
- X-22-160AS, KF6001, KF6002, BY16-201, and XF42-B0970 are preferable.
- the terminal alcohol polyester (f) represented by the following formula (6) can be used in combination with the above-mentioned both-end carbinol-modified silicone oil (e) as necessary.
- R 8 and R 9 each independently represents an alkylene group having 1 to 10 carbon atoms, and k represents an average value of 1 to 100
- R 8 include linear alkylene groups having 1 to 10 carbon atoms such as ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, isopropylene, ethylbutylpropylene, isobutylene, Examples thereof include an alkylene group having a branched chain having 1 to 10 carbon atoms such as isopentylene, neopentylene and diethylpentylene, and an alkylene group having a cyclic structure such as cyclopentanedimethylene and cyclohexanedimethylene. Among these, an alkylene group having a branched chain having 1 to 10 carbon atoms or an alkylene group having a cyclic structure is preferable. It is preferable from the viewpoint.
- R 9 examples include linear alkylene groups having 1 to 10 carbon atoms such as ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, isopropylene, ethylbutylpropylene, isobutylene, Examples thereof include an alkylene group having a branched chain having 1 to 10 carbon atoms such as isopentylene, neopentylene and diethylpentylene, and an alkylene group having a cyclic structure such as cyclopentanedimethylene and cyclohexanedimethylene.
- a linear alkylene group having 1 to 10 carbon atoms is preferable, and propylene, butylene, pentylene, and hexylene are particularly preferable from the viewpoint of adhesion of a cured product to a substrate.
- k is an average value of 1 to 100, preferably 2 to 40, more preferably 3 to 30.
- the weight average molecular weight (Mw) of the terminal alcohol polyester (f) is usually 500 to 20000, preferably 500 to 5000, and more preferably 500 to 3000. If the weight average molecular weight is less than 500, the cured product hardness of the curable resin composition of the present invention may be too high and cracks may occur in a heat cycle test or the like, and if the weight average molecular weight is more than 20000, the cured product becomes sticky. May occur.
- the weight average molecular weight means a weight average molecular weight (Mw) calculated in terms of polystyrene based on a value measured under the following conditions using GPC (gel permeation chromatography).
- Examples of the terminal alcohol polyester (f) represented by the formula (6) include polyester polyols having an alcoholic hydroxyl group at the terminal. Specific examples thereof are polyester polyols, Kyowapol 1000 PA, 2000 PA, 3000 PA, 2000 BA (all manufactured by Kyowa Hakko Chemical Co., Ltd.); Adeka New Ace Y9-10, YT-101 (all ADEKA ( Plaxel 220EB, 220EC (both manufactured by Daicel Chemical Industries); Polylite OD-X-286, OD-X-102, OD-X-355, OD-X-2330, OD-X-240, OD-X-668, OD-X-2554, OD-X-2108, OD-X-2376, OD-X-2044, OD-X-688, OD-X-2068, OD-X-2547, OD-X-2420, OD-X-2523, OD-X-2555 (all IC Co., Ltd.); HS2H-201AP, HS2H-3
- the amount of terminal alcohol polyester (f) used is usually 0.5 to 200 parts by weight, preferably 5 to 50 parts by weight, more preferably 100 parts by weight of carbinol-modified silicone oil (e) at both ends. Is 10 to 30 parts by weight. If the amount is less than 0.5 part by weight, the mechanical strength of the cured product may be reduced. If the amount is more than 200 parts by weight, the heat-resistant transparency of the cured product is lowered and the viscosity of the polyvalent carboxylic acid (Bb) to be obtained is significantly increased. Sometimes. From the viewpoint of lowering the glass transition temperature and lowering the storage elastic modulus at 0 ° C., 15 to 30 parts by weight is preferable.
- the compound (g) having one or more carboxylic anhydride groups in the molecule includes, for example, succinic anhydride, methyl succinic anhydride, ethyl succinic anhydride, 2,3-butanedicarboxylic anhydride, 2,4 -Saturated aliphatic carboxylic anhydrides such as pentanedicarboxylic anhydride, 3,5-heptanedicarboxylic anhydride, 1,2,3,4-butanetetracarboxylic dianhydride, maleic anhydride, dodecyl succinic acid Unsaturated aliphatic carboxylic anhydrides such as anhydrides, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, 1,3-cyclohexanedicarboxylic anhydride, norbornane-2,3-dicarboxylic anhydride, methyl Norbornane-2,3-dicarboxylic acid anhydride, nadic acid
- the compound (g) having one or more carboxylic acid anhydride groups in the molecule can be used alone or in combination.
- the polyvalent carboxylic acid (Bb) is liquid at room temperature and the cured product obtained by curing the polyvalent carboxylic acid (Bb) and the epoxy resin is excellent in transparency
- hexahydrophthalic anhydride, methyl Hexahydrophthalic anhydride, norbornane-2,3-dicarboxylic anhydride, methylnorbornane-2,3-dicarboxylic anhydride, 1,2,4-cyclohexanetricarboxylic acid-1,2-anhydride, 1,2 3,4-butanetetracarboxylic dianhydride is preferred. More preferred are methylhexahydrophthalic anhydride and 1,2,4-cyclohexanetricarboxylic acid-1,2-anhydride, and particularly preferred is methylhexahydrophthalic anhydride.
- the reaction between the both-end carbinol-modified silicone oil (e) (and optionally the terminal alcohol polyester (f)) and the compound (g) having one or more carboxylic acid anhydride groups in the molecule is not conducted in a solvent. It can also be performed with a solvent.
- the both-end carbinol-modified silicone oil (e) represented by the formula (5) (and the terminal alcohol polyester (f) if necessary) and one or more carboxylic anhydride groups in the molecule Any solvent that does not react with the compound (g) can be used without particular limitation.
- solvents examples include aprotic polar solvents such as dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran and acetonitrile, ketones such as methyl ethyl ketone, cyclopentanone and methyl isobutyl ketone, toluene and xylene.
- aprotic polar solvents such as dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran and acetonitrile
- ketones such as methyl ethyl ketone, cyclopentanone and methyl isobutyl ketone, toluene and xylene.
- An aromatic hydrocarbon etc. are mentioned, Among these, an aromatic hydrocarbon and ketones are preferable.
- These solvents may be used alone or in combination of two or more.
- the amount of the solvent used is not particularly limited, but the above-mentioned carbinol-modified silicone oil (e) (and optionally terminal alcohol polyester (f) if necessary) and a compound having one or more carboxylic anhydride groups ( It is usually preferable to use 0.1 to 300 parts by weight per 100 parts by weight of the total weight of g).
- a catalyst may be used for the reaction.
- usable catalysts include hydrochloric acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, paratoluenesulfonic acid, nitric acid, trifluoroacetic acid, trichloroacetic acid and other acidic compounds, water Metal hydroxides such as sodium oxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, amine compounds such as triethylamine, tripropylamine, tributylamine, pyridine, dimethylaminopyridine, 1,8-diazabicyclo [5.4.
- heterocyclic compounds such as undec-7-ene, imidazole, triazole, tetrazole, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, Methyl ethylammonium hydroxide, trimethylpropylammonium hydroxide, trimethylbutylammonium hydroxide, trimethylcetylammonium hydroxide, trioctylmethylammonium hydroxide, tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide, tetramethylammonium Examples include quaternary ammonium salts such as acetate and trioctylmethylammonium acetate. These catalysts may be used alone or in combination of two or more. Of these, triethylamine, pyridine
- two or more acid anhydrides (Ba) and polyvalent carboxylic acids (Bb) may be used in combination.
- solid polycarboxylic acid (Bb) when solid polycarboxylic acid (Bb) is used in applications where liquid is required at room temperature (25 ° C.) such as sealing of optical semiconductors, liquid acid anhydride (Ba) is used in combination as a liquid mixture. It is desirable to do.
- the acid anhydride (Ba) can be used in a proportion of 0.5 to 99.5% by weight of the total of the acid anhydride (Ba) and the polyvalent carboxylic acid (Bb).
- the acid anhydride (Ba) and / or the polyvalent carboxylic acid (Bb) are used in combination as the epoxy resin curing agent, the acid anhydride (Ba) and / or the polyvalent carboxylic acid (Bb)
- the proportion of the total amount in the total curing agent is preferably 30% by weight or more, particularly preferably 40% by weight or more.
- the curing agent that can be used in combination include amine compounds, amide compounds, phenol compounds, and the like.
- curing agents that can be used include amines and polyamide compounds (diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, dicyandiamide, polyamide resin synthesized from ethylenediamine and dimer of linolenic acid, etc.)
- Polyphenols bisphenol A, bisphenol F, bisphenol S, fluorene bisphenol, terpene diphenol, 4,4'-biphenol, 2,2'-biphenol, 3,3 ', 5,5'-tetramethyl- [ 1,1′-biphenyl] -4,4′-diol, hydroquinone, resorcin, naphthalenediol, tris- (4-hydroxyphenyl) methane, 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane, fe (Phenol, alkyl-substituted
- halogenated bisphenols such as tetrabromobisphenol A, condensates of terpenes and phenols, etc. Imidazole, trifluoroborane -. Amine complex, guanidine derivatives, etc.) and the like, but the invention is not limited to these may be used alone, or two or more may be used.
- the blending ratio of the epoxy resin (A) and the epoxy resin curing agent (B) is 0.5 to 1.2 equivalents of the curing agent with respect to 1 equivalent of the epoxy groups of all epoxy resins. It is preferable to use it.
- the curing agent is less than 0.5 equivalent or more than 1.2 equivalent with respect to 1 equivalent of epoxy group, curing may be incomplete and good cured properties may not be obtained.
- a curing accelerator can be used together with the epoxy resin curing agent (B). Since the curing accelerator is excellent in transparency, an ammonium salt-based curing accelerator, a phosphonium salt-based curing accelerator, and a metal soap-based curing accelerator are particularly excellent.
- the ammonium salt curing accelerator include tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylethylammonium hydroxide, trimethylpropylammonium hydroxide, trimethylbutylammonium hydroxide.
- Trimethylcetylammonium hydroxide Trimethylcetylammonium hydroxide, trioctylmethylammonium hydroxide, tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide, tetramethylammonium acetate, trioctylmethylammonium acetate and the like.
- the phosphonium salt-based curing accelerator include ethyltriphenylphosphonium bromide, tetraphenylphosphonium tetraphenylborate, methyltributylphosphonium dimethylphosphate, methyltributylphosphonium diethylphosphate, and the like.
- the metal soap-based curing accelerator examples include tin octylate, cobalt octylate, zinc octylate, manganese octylate, calcium octylate, sodium octylate, and potassium octylate. These curing accelerators may be used alone or in combination of two or more. Among these curing accelerators, trimethyl cetyl ammonium hydroxide, methyl tributyl phosphonium dimethyl phosphate, tin octylate, zinc octylate, and manganese octylate are preferable.
- calcium stearate in order to obtain a cured product excellent in transparency and sulfidation resistance, calcium stearate, zinc carboxylate (zinc 2-ethylhexanoate, zinc stearate, zinc behenate, zinc myristylate) and zinc phosphate ester ( Zinc compounds such as zinc octyl phosphate and zinc stearyl phosphate are preferably used.
- the curing accelerator is usually used in the range of 0.001 to 15 parts by weight with respect to 100 parts by weight of the epoxy resin (A).
- the curable resin composition of the present invention it is possible to supplement the viscosity adjustment of the composition and the hardness of the cured product by using a coupling agent as necessary.
- a coupling agent examples include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 2- (3,4-epoxycyclohexyl) ethyl.
- Trimethoxysilane N- (2-aminoethyl) 3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-mercaptopropyltri Methoxysilane, vinyltrimethoxysilane, N- (2- (vinylbenzylamino) ethyl) 3-aminopropyltrimethoxysilane hydrochloride, 3-methacryloxypropyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloro Silane coupling agents such as propyltrimethoxysilane; isopropyl (N-ethylaminoethylamino) titanate, isopropyl triisostearoyl titanate, titanium di (dioctyl pyrophosphate) oxyacetate
- the curable resin composition of the present invention it is possible to supplement mechanical strength without impairing transparency by using a nano-order level inorganic filler as necessary.
- a filler having an average particle size of 500 nm or less, particularly an average particle size of 200 nm or less.
- examples of inorganic fillers include crystalline silica, fused silica, alumina, zircon, calcium silicate, calcium carbonate, silicon carbide, silicon nitride, boron nitride, zirconia, fosterite, steatite, spinel, titania, talc, and the like.
- the present invention is not limited to these.
- These fillers may be used alone or in combination of two or more.
- the content of these inorganic fillers is preferably an amount occupying 0 to 95% by weight in the curable resin composition of the present invention.
- a phosphor can be added to the curable resin composition of the present invention as necessary.
- the phosphor has, for example, a function of forming white light by absorbing a part of blue light emitted from a blue LED element and emitting wavelength-converted yellow light.
- the optical semiconductor is sealed.
- fluorescent substance A conventionally well-known fluorescent substance can be used, For example, the rare earth element aluminate, thio gallate, orthosilicate, etc. are illustrated.
- phosphors such as a YAG phosphor, a TAG phosphor, an orthosilicate phosphor, a thiogallate phosphor, and a sulfide phosphor can be mentioned, and YAlO 3 : Ce, Y 3 Al 5 O 12 : Ce, Y 4 Al 2 O 9 : Ce, Y 2 O 2 S: Eu, Sr 5 (PO 4 ) 3 Cl: Eu, (SrEu) O.Al 2 O 3 and the like are exemplified.
- the particle size of the phosphor those having a particle size known in this field are used, and the average particle size is preferably 1 to 250 ⁇ m, particularly preferably 2 to 50 ⁇ m.
- the amount added is usually 1 to 80 parts by weight, preferably 5 to 60 parts by weight, based on 100 parts by weight of the resin component.
- a thixotropic imparting agent such as fine silica powder (also referred to as “aerosil” or “aerosol”) can be added for the purpose of preventing sedimentation of various phosphors during curing.
- silica fine powder include Aerosil 50, Aerosil 90, Aerosil 130, Aerosil 200, Aerosil 300, Aerosil 380, Aerosil OX50, Aerosil TT600, Aerosil R972, Aerosil R974, AerosilR202, AerosilR202, AerosilR202 Aerosil R805, RY200, RX200 (made by Nippon Aerosil Co., Ltd.), etc. are mentioned.
- the curable resin composition of the present invention can contain an amine compound as a light stabilizer, or a phosphorus compound and a phenol compound as an antioxidant.
- the amine compound include tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, tetrakis (2,2,6,6- Totramethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, 1,2,3,4-butanetetracarboxylic acid and 1,2,2,6,6-pentamethyl-4-piperidinol and 3 , 9-bis (2-hydroxy-1,1-dimethylethyl) -2,4,8,10-tetraoxaspiro [5.5] undecane mixed ester, decanedioic acid bis (2,2,6 , 6-Tetramethyl-4-piperidyl) sebacate, bis (1-undecanoxy-2
- the following commercially available products can be used as the amine compound as the light stabilizer.
- the commercially available amine compound is not particularly limited.
- the phosphorus compound is not particularly limited, and for example, 1,1,3-tris (2-methyl-4-ditridecyl phosphite-5-tert-butylphenyl) butane, distearyl pentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, phenylbisphenol A pentaerythritol diphosphite, Dicyclohexylpentaerythritol diphosphite, tris (diethylphenyl) phosphite, tris (di-isopropylphenyl) phosphite, tris (di-n-butylphenyl) phosphite, tris (2,4-
- the commercially available phosphorus compounds are not particularly limited.
- the commercially available phosphorus compounds are not particularly limited.
- the phenol compound is not particularly limited, and examples thereof include 2,6-di-tert-butyl-4-methylphenol and n-octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate.
- the commercially available phenolic compounds are not particularly limited. , ADK STAB AO-30, ADK STAB AO-40, ADK STAB AO-50, ADK STAB AO-60, ADK STAB AO-70, ADK STAB AO-80, ADK STAB AO-90, ADK STAB AO-330, Sumitizer GA-80 manufactured by Sumitomo Chemical Co., Ltd. , Sumilizer MDP-S, Sumil izer BBM-S, SumizerzGM, SumizerilGS (F), SumizerGP, and the like.
- THINUVIN 328, THINUVIN 234, THINUVIN 326, THINUVIN 120, THINUVIN 477, THINUVIN 479, CHIMASSORB 2020FDL, CHIMASSORB 119FL and the like can be mentioned as manufactured by Ciba Specialty Chemicals.
- the amount of the compound is not particularly limited, but with respect to the total weight of the curable resin composition of the present invention, It is in the range of 0.005 to 5.0% by weight.
- the curable resin composition of the present invention is obtained by sufficiently mixing additives such as an epoxy resin (A), an epoxy resin curing agent (B), a curing accelerator, a coupling agent, an antioxidant, and a light stabilizer.
- a curable resin composition can be prepared and used as a sealing material.
- a mixing method a kneader, a three-roll, a universal mixer, a planetary mixer, a homomixer, a homodisper, a bead mill or the like is used to mix at room temperature or warm.
- Optical semiconductor elements such as high-intensity white LEDs are generally GaAs, GaP, GaAlAs, GaAsP, AlGa, InP, GaN, InN, AlN, InGaN laminated on a substrate of sapphire, spinel, SiC, Si, ZnO or the like.
- Such a semiconductor chip is bonded to a lead frame, a heat sink, or a package using an adhesive (die bond material).
- a wire such as a gold wire is connected to pass an electric current.
- the semiconductor chip is sealed with a sealing material such as an epoxy resin in order to protect it from heat and moisture and play a role of a lens.
- the curable resin composition of this invention can be used for this sealing material.
- an injection method in which the sealing material is injected into the mold frame in which the optical semiconductor element is fixed is inserted and then heat-cured and then molded, and the sealing material is injected on the mold in advance.
- a compression molding method is used in which an optical semiconductor element fixed on a substrate is immersed therein and heat-cured and then released from a mold.
- the injection method include dispenser, transfer molding, injection molding and the like.
- methods such as hot air circulation, infrared rays and high frequency can be used.
- the heating conditions are preferably 80 to 230 ° C. for about 1 minute to 24 hours.
- the purpose of reducing internal stress generated during heat-curing for example, after pre-curing at 80 to 120 ° C.
- X to Y indicates a range from X to Y, and the range includes X and Y.
- Synthesis Example 1 (Synthesis example of a silicone skeleton epoxy resin in which silanol-terminated silicone oil (a) and epoxy group-containing silicon compound (b) are produced through a two-stage production process) (Manufacturing process 1) 394 parts of 2- (3,4 epoxycyclohexyl) ethyltrimethoxysilane, polydimethyldiphenylsiloxane having a silanol group with a molecular weight of 1700 (measured by GPC) (having 0.18 mol of phenyl group per 1 mol of methyl group) 475 Part, 4 parts of 0.5% KOH methanol solution and 36 parts of isopropyl alcohol were charged into a reaction vessel, and the temperature was raised to 75 ° C.
- Synthesis Example 2 (Synthesis Example of Silicone Skeleton Epoxy Resin Produced by Silanol-Terminated Silicone Oil (a) and Epoxy Group-Containing Silicon Compound (b) Through Two-Step Manufacturing Process) (Manufacturing process 1) 197 parts of 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, polydimethyldiphenylsiloxane having a silanol group having a molecular weight of 1700 (measured by GPC) (having 0.18 mol of phenyl group per 1 mol of methyl group) 534 Part, 4 parts of 0.5% KOH methanol solution and 36 parts of isopropyl alcohol were charged into a reaction vessel, and the temperature was raised to 75 ° C.
- Synthesis Example 3 (Synthesis Example of Silicone Skeleton Epoxy Resin Made from Silanol-Terminated Silicone Oil (a) and Epoxy Group-Containing Silicon Compound (b) Through Two-Step Manufacturing Process)
- Synthesis Example 4 (Synthesis example of polyvalent carboxylic acid having silicone skeleton)
- 50 parts of both-end carbinol-modified silicone X22-160AS manufactured by Shin-Etsu Chemical Co., Ltd.
- Ricacid MH methyl hexahydrophthalic anhydride, 15.4 parts (manufactured by Shin Nippon Rika Co., Ltd.) were charged into a reaction vessel, heated to 80 ° C., and GPC was measured after 4 hours. The peak of Ricacid MH disappeared.
- Synthesis Example 5 (Synthesis example of polyvalent carboxylic acid having silicone skeleton and polyester skeleton) A glass separable flask equipped with a stirrer, a Dimroth condenser and a thermometer, 47.1 parts carbinol-modified silicone X22-160AS (manufactured by Shin-Etsu Chemical Co., Ltd.), Adeka New Ace Y9- which is a polyester polyol 10 (polyester polyol manufactured by ADEKA Corporation, wherein R 8 is a neopentylene group and R 9 is a butylene group in the above formula (6)), Ricacid BT-100 (1,2,3,4-butanetetra) Carrying out 2.5 parts of carboxylic dianhydride (manufactured by Shin Nippon Rika Co., Ltd.) and 16.6 parts of Jamaicacid MH (methylhexahydrophthalic anhydride, Shin Nippon Rika Co., Ltd.) at 140 ° C.
- Synthesis Example 6 (Synthesis Example of Mixture of Acid Anhydride and Multivalent Carboxylic Acid) A glass separable flask equipped with a stirrer, a Dimroth condenser, and a thermometer, 12 parts of tricyclodecane dimethanol (TCD-AL, manufactured by Oxea), RIKACID MH (methylhexahydrophthalic anhydride, Shin Nippon Rika Co., Ltd.) )) 73 parts were charged into a reaction vessel (a glass four-necked flask equipped with a stirrer, Dimroth, and thermometer), heated to 40 ° C. for 1 hour, and then reacted at 60 ° C. for 1 hour, and GPC was measured.
- TCD-AL tricyclodecane dimethanol
- RIKACID MH methylhexahydrophthalic anhydride, Shin Nippon Rika Co., Ltd.
- a curing agent (B-3) which is a mixture of a polyvalent carboxylic acid having a cyclic aliphatic hydrocarbon group (tricyclodecanedimethyl) as a main skeleton and an acid anhydride (methylhexahydrophthalic anhydride).
- the functional group equivalent of the obtained curing agent (B-3) was 171 g / eq.
- the carboxylic acid and acid anhydride groups are each considered as one functional group).
- the viscosity was 15000 mPa ⁇ s, and the appearance was a colorless and transparent liquid.
- Example 1 100 parts of silicone skeleton epoxy resin (A-1) obtained in Synthesis Example 1, 5 parts of ERL-4221 (3,4-epoxycyclohexylmethyl- (3,4-epoxy) cyclohexylcarboxylate, manufactured by Dow Chemical), epoxy 74 parts of polyvalent carboxylic acid (B-1) obtained in Synthesis Example 4 as a resin curing agent, 8 parts of PRIPOL 1009 (dimer acid which is a reduced product of unsaturated fatty acid multimer, manufactured by Claude Japan Co., Ltd.), curing 1 part of zinc 2-ethylhexanoate was added as an accelerator, mixed and defoamed for 5 minutes to obtain a curable resin composition for optical semiconductor encapsulation of the present invention.
- A-1 silicone skeleton epoxy resin obtained in Synthesis Example 1
- ERL-4221 3,4-epoxycyclohexylmethyl- (3,4-epoxy) cyclohexylcarboxylate, manufactured by Dow Chemical
- Example 2 70 parts of silicone skeleton epoxy resin (A-1) obtained in Synthesis Example 1, 30 parts of silicone skeleton epoxy resin (A-3) obtained in Synthesis Example 3, ERL-4221 (3,4-epoxycyclohexylmethyl- 5 parts of (3,4-epoxy) cyclohexyl carboxylate, manufactured by Dow Chemical), 71 parts of polycarboxylic acid (B-2) obtained in Synthesis Example 5 as an epoxy resin curing agent, 2-ethylhexane as a curing accelerator 0.5 parts of zinc acid was added, mixed and degassed for 5 minutes to obtain a curable resin composition for optical semiconductor encapsulation of the present invention.
- Comparative Example 1 40 parts of silicone skeleton epoxy resin (A-1) obtained in Synthesis Example 1, 60 parts of silicone skeleton epoxy resin (A-3) obtained in Synthesis Example 3, ERL-4221 (3,4-epoxycyclohexylmethyl- 5 parts of (3,4-epoxy) cyclohexyl carboxylate, manufactured by Dow Chemical), 87 parts of polycarboxylic acid (B-2) obtained in Synthesis Example 5 as an epoxy resin curing agent, PRIPOL 1009 (multimer of unsaturated fatty acids) 10 parts of dimer acid, a product of Cloda Japan Co., Ltd.) and 1.2 parts of zinc 2-ethylhexanoate as a curing accelerator, mixed and degassed for 5 minutes to cure for optical semiconductor encapsulation A functional resin composition was obtained.
- Comparative Example 2 50 parts of silicone skeleton epoxy resin (A-1) obtained in Synthesis Example 1, 50 parts of silicone skeleton epoxy resin (A-2) obtained in Synthesis Example 2, ERL-4221 (3,4-epoxycyclohexylmethyl- 5 parts of (3,4-epoxy) cyclohexyl carboxylate, manufactured by Dow Chemical), 23 parts of a mixture of acid anhydride and polycarboxylic acid obtained in Synthesis Example 6 as an epoxy resin curing agent (B-3), curing acceleration 0.2 parts of 2-ethylhexanoic acid zinc was added as an agent, mixed and defoamed for 5 minutes to obtain a curable resin composition for optical semiconductor encapsulation.
- Comparative Example 3 50 parts of silicone skeleton epoxy resin (A-1) obtained in Synthesis Example 1, 50 parts of silicone skeleton epoxy resin (A-2) obtained in Synthesis Example 2, obtained in Synthesis Example 6 as an epoxy resin curing agent 26 parts of the resulting acid anhydride and polycarboxylic acid mixture (B-3) and 0.8 part of zinc 2-ethylhexanoate as a curing accelerator were added, mixed and degassed for 5 minutes to seal the optical semiconductor. A curable resin composition was obtained.
- casting was performed so that the opening was a flat surface.
- pre-curing at 120 ° C. for 1 hour, it was cured at 150 ° C. for 3 hours to seal the surface-mounted LED.
- the heat cycle test shown below was performed, and the change in the appearance was observed.
- the curable resin composition of the present invention has a glass transition temperature (Tg) measured by DMA method in the range of ⁇ 10 to 10 ° C. and a storage elastic modulus at 0 ° C. measured by DMA method in the range of 0 to 150 MPa.
- Tg glass transition temperature
- DMA method a storage elastic modulus at 0 ° C. measured by DMA method in the range of 0 to 150 MPa.
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Abstract
La présente invention concerne une composition de résine durcissable présentant une excellente résistance aux cycles thermiques, destinée à sceller un élément semi-conducteur optique. La présente invention est caractérisée en ce que la température de transition vitreuse (Tg) du matériau durci telle que mesurée par le procédé DMA est située dans la plage allant de −10 à 10 °C, et que le module de conservation à 0 °C de celui-ci tel que mesuré par le procédé DMA est situé dans la plage allant de 0 à 150 MPa ; la présente invention contient une résine époxy (A) et un agent de durcissement de résine époxy, et la résine époxy (A) est de préférence une résine époxy à squelette à base de silicium.
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WO2013173074A1 (fr) * | 2012-05-15 | 2013-11-21 | Dow Corning Corporation | Procédé de fabrication d'un dispositif semi-conducteur encapsulé et dispositif semi-conducteur encapsulé |
CN111690309A (zh) * | 2020-07-16 | 2020-09-22 | 程浩源 | 一种常温固化水性环氧树脂涂料及其制备方法 |
CN113242873A (zh) * | 2018-12-21 | 2021-08-10 | 昭和电工材料株式会社 | 密封组合物及半导体装置 |
WO2023079753A1 (fr) * | 2021-11-08 | 2023-05-11 | 株式会社レゾナック | Composition de résine époxy, dispositif composant électronique et procédé de fabrication de dispositif composant électronique |
WO2023079752A1 (fr) * | 2021-11-08 | 2023-05-11 | 株式会社レゾナック | Composé époxyde, résine époxyde et matériau d'étanchéité |
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JP6395597B2 (ja) * | 2014-12-25 | 2018-09-26 | マクセルホールディングス株式会社 | ダイシング用粘着テープおよび半導体チップの製造方法 |
CN115244100A (zh) * | 2020-02-21 | 2022-10-25 | 陶氏东丽株式会社 | 无溶剂型的光固化性液态组合物、其固化物、包含该组合物的光学填充剂、以及包括由其固化物构成的层的显示装置 |
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WO2010071168A1 (fr) * | 2008-12-19 | 2010-06-24 | 日本化薬株式会社 | Composé d'acide carboxylique et composition de résine époxy le contenant |
WO2011043400A1 (fr) * | 2009-10-06 | 2011-04-14 | 日本化薬株式会社 | Composition d'acide polycarboxylique, son procédé de préparation, et compositions de résines durcissables la contenant |
WO2011108588A1 (fr) * | 2010-03-02 | 2011-09-09 | 日本化薬株式会社 | Composition de résine durcissable et article durci obtenu à partir de celle-ci |
WO2011108516A1 (fr) * | 2010-03-02 | 2011-09-09 | 日本化薬株式会社 | Procédé de fabrication d'un organopolysiloxane, organopolysiloxane obtenu par le procédé, et composition qui contient l'organopolysiloxane |
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- 2011-09-27 JP JP2011210118A patent/JP6150415B2/ja not_active Expired - Fee Related
-
2012
- 2012-09-26 WO PCT/JP2012/074789 patent/WO2013047620A1/fr active Application Filing
- 2012-09-27 TW TW101135510A patent/TW201323469A/zh unknown
Patent Citations (4)
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WO2010071168A1 (fr) * | 2008-12-19 | 2010-06-24 | 日本化薬株式会社 | Composé d'acide carboxylique et composition de résine époxy le contenant |
WO2011043400A1 (fr) * | 2009-10-06 | 2011-04-14 | 日本化薬株式会社 | Composition d'acide polycarboxylique, son procédé de préparation, et compositions de résines durcissables la contenant |
WO2011108588A1 (fr) * | 2010-03-02 | 2011-09-09 | 日本化薬株式会社 | Composition de résine durcissable et article durci obtenu à partir de celle-ci |
WO2011108516A1 (fr) * | 2010-03-02 | 2011-09-09 | 日本化薬株式会社 | Procédé de fabrication d'un organopolysiloxane, organopolysiloxane obtenu par le procédé, et composition qui contient l'organopolysiloxane |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013173074A1 (fr) * | 2012-05-15 | 2013-11-21 | Dow Corning Corporation | Procédé de fabrication d'un dispositif semi-conducteur encapsulé et dispositif semi-conducteur encapsulé |
CN113242873A (zh) * | 2018-12-21 | 2021-08-10 | 昭和电工材料株式会社 | 密封组合物及半导体装置 |
CN113242873B (zh) * | 2018-12-21 | 2024-04-19 | 株式会社力森诺科 | 密封组合物及半导体装置 |
CN111690309A (zh) * | 2020-07-16 | 2020-09-22 | 程浩源 | 一种常温固化水性环氧树脂涂料及其制备方法 |
WO2023079753A1 (fr) * | 2021-11-08 | 2023-05-11 | 株式会社レゾナック | Composition de résine époxy, dispositif composant électronique et procédé de fabrication de dispositif composant électronique |
WO2023079752A1 (fr) * | 2021-11-08 | 2023-05-11 | 株式会社レゾナック | Composé époxyde, résine époxyde et matériau d'étanchéité |
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JP6150415B2 (ja) | 2017-06-21 |
JP2013071950A (ja) | 2013-04-22 |
TW201323469A (zh) | 2013-06-16 |
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