JP2008544067A - 硬化触媒、組成物、電子機器及び関連する方法 - Google Patents
硬化触媒、組成物、電子機器及び関連する方法 Download PDFInfo
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- JP2008544067A JP2008544067A JP2008518211A JP2008518211A JP2008544067A JP 2008544067 A JP2008544067 A JP 2008544067A JP 2008518211 A JP2008518211 A JP 2008518211A JP 2008518211 A JP2008518211 A JP 2008518211A JP 2008544067 A JP2008544067 A JP 2008544067A
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- catalyst
- composition
- lewis acid
- anhydride
- resin
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 108
- 239000003054 catalyst Substances 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229910000679 solder Inorganic materials 0.000 claims abstract description 40
- 229920005989 resin Polymers 0.000 claims abstract description 36
- 239000011347 resin Substances 0.000 claims abstract description 36
- -1 heterocyclic aromatic organic compound Chemical class 0.000 claims abstract description 32
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 28
- 239000002841 Lewis acid Substances 0.000 claims abstract description 27
- 239000000463 material Substances 0.000 claims abstract description 25
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 21
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 239000003822 epoxy resin Substances 0.000 claims description 12
- 229920000647 polyepoxide Polymers 0.000 claims description 12
- 150000008064 anhydrides Chemical class 0.000 claims description 11
- 229910000085 borane Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 7
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 230000004907 flux Effects 0.000 claims description 6
- 229910052738 indium Inorganic materials 0.000 claims description 5
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 239000004844 aliphatic epoxy resin Substances 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- 229910052716 thallium Inorganic materials 0.000 claims description 3
- 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 claims description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 239000003063 flame retardant Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims 1
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical group CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003607 modifier Substances 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 27
- 230000008018 melting Effects 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 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 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000003003 phosphines Chemical group 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XINAQPROOGNKIN-UHFFFAOYSA-N C1C(C(=O)O)CCC=C1CC1=CCCCC1 Chemical compound C1C(C(=O)O)CCC=C1CC1=CCCCC1 XINAQPROOGNKIN-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- 239000012530 fluid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 2
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 2
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011231 conductive filler Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- QXALIERKYGCHHA-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)borane Chemical group BC1=C(F)C(F)=C(F)C(F)=C1F QXALIERKYGCHHA-UHFFFAOYSA-N 0.000 description 1
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 1
- NOQONXWBCSGVGF-UHFFFAOYSA-N 1,2,4-triphenylimidazole Chemical class C=1C=CC=CC=1N1C=C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 NOQONXWBCSGVGF-UHFFFAOYSA-N 0.000 description 1
- ZWOULFZCQXICLZ-UHFFFAOYSA-N 1,3-dimethyl-1-phenylurea Chemical compound CNC(=O)N(C)C1=CC=CC=C1 ZWOULFZCQXICLZ-UHFFFAOYSA-N 0.000 description 1
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 description 1
- YDIZFUMZDHUHSH-UHFFFAOYSA-N 1,7-bis(ethenyl)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene Chemical compound C12OC2C=CC2(C=C)C1(C=C)O2 YDIZFUMZDHUHSH-UHFFFAOYSA-N 0.000 description 1
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 1
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical class C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- BDHGFCVQWMDIQX-UHFFFAOYSA-N 1-ethenyl-2-methylimidazole Chemical compound CC1=NC=CN1C=C BDHGFCVQWMDIQX-UHFFFAOYSA-N 0.000 description 1
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- SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical class C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
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- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SSBBTCLDTXVJGT-UHFFFAOYSA-N 2-(2-propoxy-1,4-dioxan-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C(CC)OC1(OCCOC1)C1C2C(CCC1)O2 SSBBTCLDTXVJGT-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- YAXVEVGFPVWPKA-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)ethenyl]-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C=CC1=NC=CN1 YAXVEVGFPVWPKA-UHFFFAOYSA-N 0.000 description 1
- LUSCNZBJFBNVDT-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxy)cyclohexyl]oxymethyl]oxirane Chemical compound C1OC1COC1(OCC2OC2)CCCCC1 LUSCNZBJFBNVDT-UHFFFAOYSA-N 0.000 description 1
- YECWFFFKBCTNQX-UHFFFAOYSA-N 2-[[2-(cyclopenten-1-yl)phenoxy]methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1C1=CCCC1 YECWFFFKBCTNQX-UHFFFAOYSA-N 0.000 description 1
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- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
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- AKKKBXUXBCGIHM-UHFFFAOYSA-N 2-cycloheptyl-4-(oxiran-2-yl)oxepane Chemical compound C1OC1C1CC(C2CCCCCC2)OCCC1 AKKKBXUXBCGIHM-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- SIQHSJOKAUDDLN-UHFFFAOYSA-N 2-methyl-1-propylimidazole Chemical compound CCCN1C=CN=C1C SIQHSJOKAUDDLN-UHFFFAOYSA-N 0.000 description 1
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- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Natural products CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 1
- PAVNZLVXYJDFNR-UHFFFAOYSA-N 3,3-dimethyloxane-2,6-dione Chemical compound CC1(C)CCC(=O)OC1=O PAVNZLVXYJDFNR-UHFFFAOYSA-N 0.000 description 1
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】ルイス酸、並びに窒素含有分子若しくは非第三級ホスフィンのうちの一方又は両方を含んでなり、当該窒素含有分子がモノアミン若しくは複素環式芳香族有機化合物を含んでなる硬化触媒。また、第1混合物若しくは第2混合物又はその両方を含んでなる硬化性組成物。当該第1混合物は硬化性の第1樹脂及び第1触媒を含んでなってもよい。当該第1触媒はルイス酸、並びに非第三級アミン若しくは非第三級ホスフィンの一方又は両方を含んでなってもよい。当該第2混合物は硬化性の有機質の第2樹脂及び第2触媒を含んでなってもよい。当該第2触媒はルイス酸、並びにアミン若しくはホスフィンの一方又は両方を含んでなってもよい。
【選択図】図1
Description
MRbXc (I)
式中、MはB、Al、Ga、In又はTlであり、各Rは独立に同じであるか又は各々異なってもよく、約6〜約14の炭素原子数の一価の芳香族炭化水素基であってもよく、当該一価の芳香族炭化水素基が少なくとも1つの電子吸引要素又は基(−CF3、−NO2、又は、−CN)を有してもよいか、又は少なくとも2つのハロゲン原子で置換されてもよく、bは1、2又は3であってもよく、Xはハロゲン原子であってもよく、cは0、1又は2であってもよく、但しb+c=3である。
BRbXc (II)
各Rは独立に同じであるか又は各々異なってもよく、約6〜約14の炭素原子数の一価の芳香族炭化水素基であってもよく、当該一価の芳香族炭化水素基が少なくとも1つの電子吸引要素又は基(−CF3、−NO2、又は−CN)を有してもよいか、又は少なくとも2つのハロゲン原子で置換されてもよく、bは1、2又は3であってもよく、Xはハロゲン原子であってもよく、cは0、1又は2であってもよく、但しb+c=3である。
丸底の100mlのフラスコに、5gのトリス(ペンタフルオロフェニル)ボラン及び15mlの無水トルエンを添加し、懸濁液を調製した。得られる懸濁液を室温(25℃)で5分間撹拌し、反応混合液を調製した。その後、無水トルエン5ml中の0.81gのn−メチルイミダゾール溶液を液滴で反応混合液に添加した。n−メチルイミダゾールの添加完了後、反応混合液は透明に変化した。反応混合液を更に1時間室温で撹拌した。撹拌開始の約5分後に白色固体の形成が観察された。その後、30mlのヘキサンを反応混合液に添加し、フラスコを一晩冷蔵庫に保存した。翌日、白色固体をフィルター濾過し、真空乾燥し、複合体生成物4.33gを得た。複合体の構造を、1H、13C及び19F NMRで確認した。
第1樹脂(RSL−1739)及び第2樹脂(EXA−4700)(両方ともエポキシベース)を、4−メチルヘキサヒドロフタル酸無水物(MHHPA)、グリセロール及び5,5’−(1,1,3,3,5−ヘキサメチル−1,5−トリシロキサンジイル)ビス[ヘキサヒドロ−4,7−メタノイソベンゾフラン−1,3−ジオン](TriSNBA)を室温で混合し、混合物を調製した。得られる混合物を室温で30分間混合した。下記の表に記載の触媒(POLYCAT SA−1又は本発明の一実施態様に係る触媒)及び任意の添加材を混合物に添加し、調製物を調製した。調製物を室温で約30分間混合し、室温で少なくとも30分間のガス除去し、硬化性組成物を調製した。得られる硬化性組成物を−40℃で保存した。
洗浄された銅積層FR−4ボードを使用してはんだの溶融試験を実施した。硬化性組成物の一部(0.2g)を銅の積層体に添加し、少量の鉛フリーのはんだ球をその滴に添加した。その後、滴をガラススライドで覆い、銅板を260℃のピーク温度でリフローオーブン中を通過させた。はんだ球が拡散し、光学顕微鏡下で融合を観察した。
標準のFR−4ボード及び高Tg/低CTE FR−4ボードを回路組み立てに用い、電解金ニッケル合金でフラッシュ層表面仕上げを行った。両方の試験ボード上の結合パッドは、はんだマスク(Taiyo社製/PSR4000)からエッチングされる直角溝により画定される。22ゲージ針(EFD社製)を使用して、一定量の硬化性組成物を点/線パターンで部品のフットプリント領域の中央に添加し、予め20分〜最高2時間にわたり、150℃〜220℃の温度で焼成したボードを試験した。フリップチップの型を、MRSI505自動ピック/プレイス機(150gの配置力、及び500ミリ秒の配置ヘッド滞留時間)を使用して配置した。これらの試験ビヒクルのリフローは、浸漬ゾーンによる鉛フリーのプロフィール、及び約250℃〜約260℃の範囲のピーク温度を使用した、ZEPHER対流リフローオーブンを使用して実施した。リフローの後の、160℃で1時間の硬化後処理は、硬化工程を完了させるのに必要であった。組み立てられたフリップチップを、1000サイクル(滞留時間:各エクストリームで10分)にわたるエア−ツー−エア熱ショック(AATS)(−55℃〜+150℃)に供した。硬化性組成物を、熱ショック試験の間、割れ及び電気的接続に関してモニターした。
実施例3から6、及び比較実施例1において、下記の表1に示すように、単一の樹脂を使用して、添加される触媒の重量%(実施例1において調製)を変化させて、実施例2にて説明したのと同様の方法で硬化性組成物を調製した。
A.溶融性:
1.はんだ球の形態に変化なし
2.はんだが崩壊し始める
3.はんだ球が崩壊するが融合しない
4.はんだ球が崩壊し、若干の併合が観察される
5.はんだ球が崩壊し、完全な融合が観察される
B.硬化度合い:
1.リフロー後、室温で粘着性の流体
2.リフロー後、高温で低い粘性の流体、及び室温で粘着性の固体
3.リフロー後、高温で粘着性の流体、室温で固体
4.リフロー後、高温で柔軟、室温で固体
5.リフロー後、高温で固体
実施例7及び比較実施例2から6において、表3に示すように、触媒(POLYCAT SA−1)の重量%を変化させ、実施例2で説明したのと同様の方法で硬化性組成物を調製した。EXR4700対RSL1739の比率は1〜4とした。
実施例8において、硬化性組成物には実施例1の触媒を含有させた。比較実施例7には触媒としてPOLYCAT SA−Iを含有させた。実施例8及び比較実施例7には、表5に示される量の成分を含有させた。実施例8及び比較実施例7を、実施例2に開示されるのと同様の方法で調製した。
102 型
104 基板
106 電気接続
108 硬化性組成物
110 ボリューム
112 領域
114 図2
116 時間(横軸)
118 粘性(縦軸)
120 比較実施例1のグラフ
122 実施例3のグラフ
124 実施例4のグラフ
126 実施例5のグラフ
128 実施例6のグラフ
130 図3
132 温度(横軸)
134 熱フロー(縦軸)
136 実施例7のグラフ
138 比較実施例2のグラフ
140 図4
142 実施例8のグラフ
144 比較実施例7のグラフ
Claims (35)
- ルイス酸、並びに窒素含有分子若しくは非第三級ホスフィンのうちの一方又は両方を含んでなり、当該窒素含有分子がモノアミン又は複素環式芳香族有機化合物を含んでなる硬化触媒。
- 前記ルイス酸が窒素含有分子若しくは非第三級ホスフィンとの複合体若しくはアダクトの一方又は両方である、請求項1記載の触媒。
- 前記窒素含有分子が、1,8−ジアザビシクロ[5,4,0]ウンデス−7−エン又はメチルイミダゾールの一方又は両方を含んでなる、請求項1記載の触媒。
- 前記ルイス酸が三価のボランを含んでなる、請求項1記載の触媒。
- 前記ルイス酸がトリ(アリール)ボランを含んでなる、請求項4記載の触媒。
- 前記トリ(アリール)ボランが、フェニル、ペンタフルオロフェニル、2,3,5,6−テトラフルオロフェニル、2,3,4,5−テトラフルオロフェニル、3,4,5−トリフルオロフェン−1−イル、又は4−(ペンタフルオロフェニル)−2,3,5,6−テトラフルオロフェニル基のうちの1つ以上を含んでなる、請求項4記載の触媒。
- 前記ルイス酸が1つ以上の非加水分解性ハロゲンを含んでなる、請求項6記載の触媒。
- 前記ルイス酸が式(I)で表される構造を有する、請求項1記載の触媒。
MRbXc (I)
(式中、MはB、Al、Ga、In又はTlであり、各Rは約6〜約14の炭素原子数の、独立に同じであるか又は各々異なる一価の芳香族炭化水素基であり、前記一価の芳香族炭化水素基が任意に、1つの電子吸引性の要素又は基を有するか、又は少なくとも2つのハロゲン原子で置換されてもよく、bは1、2又は3で、Xはハロゲン原子で、cは0、1又は2で、但しb+c=3である。) - A)硬化性の第1樹脂及び第1触媒を含んでなり、当該第1触媒がルイス酸、並びに非第三級アミン若しくは非第三級ホスフィンの一方又は両方を含んでなる第1混合物か、
B)硬化性の有機質の第2樹脂及び第2触媒を含んでなり、当該第2触媒がルイス酸、並びにアミン若しくはホスフィンの一方又は両方を含んでなる第2混合物か、
又はA)及びB)の両方を含んでなる硬化性組成物。 - 前記第1触媒と前記第2触媒が各々異なる、請求項9記載の組成物。
- 前記第1触媒と前記第2触媒が同じである、請求項9記載の組成物。
- 前記第1触媒が150℃超の温度で前記第1樹脂を硬化させることができる、請求項9記載の組成物。
- 前記第2触媒が150℃超の温度で前記第2樹脂を硬化させることができる、請求項9記載の組成物。
- 所定の基準に応答してin situで融剤を形成できる成分を更に含んでなる、請求項9記載の組成物。
- 所定の基準に応答して融剤を解放させることができる成分を更に含んでなる請求項9記載の組成物。
- 前記ルイス酸がトリ(アリール)ボランを含んでなる、請求項9記載の組成物。
- 前記トリ(アリール)ボランがB(C6F5)3を含んでなる、請求項16記載の組成物。
- 前記トリ(アリール)ボランがフェニル、ペンタフルオロフェニル、2,3,5,6−テトラフルオロフェニル、2,3,4,5−テトラフルオロフェニル、3,4,5−トリフルオロフェン−1−イル及び4−(ペンタフルオロフェニル)−2,3,5,6−テトラフルオロフェニルのうちの1つ以上を含んでなる、請求項16記載の組成物。
- 前記トリ(アリール)ボラン成分が実質的にペンタフルオロフェニル基からなる、請求項16記載の組成物。
- 前記ルイス酸が、非第三級アミン、非第三級ホスフィン、アミン又はホスフィンのうちの1つ以上と複合体を形成する、請求項9記載の組成物。
- 前記ルイス酸が式(II)で表される構造を有する、請求項9記載の組成物。
MRbXc (II)
(式中、MはB、Al、Ga、In又はTlであり、各Rは約6〜約14の炭素原子数の、独立に同じであるか又は各々異なる一価の芳香族炭化水素基であり、前記一価の芳香族炭化水素基は任意に、少なくとも1つの電子吸引性の要素又は基を有するか、又は少なくとも2つのハロゲン原子で置換されてもよく、bは1、2又は3で、Xはハロゲン原子で、cは0、1又は2で、但しb+c=3である。) - Mがホウ素である、請求項21記載の組成物。
- 前記電子吸引性の要素又は基が−CF3、−NO2又は−CNのうちの1つ以上を含んでなる、請求項21記載の組成物。
- 前記ルイス酸が1つ以上の非加水分解性ハロゲンを含んでなる、請求項9記載の触媒。
- 前記組成物中の前記触媒が、組成物の合計量に対して約0.01重量%〜約5重量%の範囲の量で存在する、請求項9記載の組成物。
- 前記硬化性樹脂が脂肪族エポキシ樹脂、脂環式エポキシ樹脂又は芳香族のエポキシ樹脂のうちの1つ以上を含んでなる、請求項9記載の組成物。
- 軟化剤、有機希釈剤、難燃剤、色素、硬化剤又は流動性調整剤のうちの1つ以上を更に含んでなる、請求項9記載の組成物。
- ナノスケールのシリカ充填材を更に含んでなる、請求項9記載の組成物。
- 硬化剤を更に含んでなる、請求項9記載の組成物。
- 前記硬化剤が1つ以上の無水物を含んでなる、請求項29記載の組成物。
- 前記無水物がカルボン酸無水物を含んでなる、請求項30記載の組成物。
- 前記無水物がフタル酸無水物、ヘキサヒドロフタル酸無水物、メチルヘキサヒドロフタル酸無水物、4−ニトロフタル酸無水物、ナフタレンテトラカルボン酸二無水物、ナフタレン無水物、テトラヒドロフタル酸無水物、安息香酸無水物、又はシロキサン二無水物のうちの1つ以上を含んでなる、請求項30記載の組成物。
- A)硬化性の第1樹脂及び第1触媒を含んでなり、前記第1触媒がルイス酸、並びにモノアミン若しくは複素環式芳香族有機化合物の一方又は両方を含んでなる第1混合物か、
B)硬化性の有機質の第2樹脂及び第2触媒を含んでなり、前記第2触媒がルイス酸、並びに窒素含有分子若しくは非第三級ホスフィンの一方又は両方を含んでなる第2混合物か、
又は上記A)とB)の両方を含んでなる硬化フィルム。 - 請求項33記載の硬化フィルムを含んでなるアンダーフィル材料と、前記フィルムの範囲内で少なくとも一部に無鉛はんだが配置されている電気接続とを含んでなる電子機器。
- 型の内部の対向面と、基板の内部の対向面により画定される領域を充填するための手段と、前記型を基板に固定することができる無鉛はんだを含む電気接続を含んでなる電子機器。
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WO2003076485A2 (en) * | 2002-03-05 | 2003-09-18 | Dow Global Technologies Inc. | Organoborane amine complex polymerization initiators and polymerizable compositions |
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JP5680668B2 (ja) * | 2010-11-05 | 2015-03-04 | 株式会社日本触媒 | カチオン硬化性樹脂組成物 |
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Also Published As
Publication number | Publication date |
---|---|
BRPI0612009A2 (pt) | 2010-10-13 |
WO2007001803A3 (en) | 2007-03-15 |
WO2007001803A2 (en) | 2007-01-04 |
EP2283922A2 (en) | 2011-02-16 |
KR20080034438A (ko) | 2008-04-21 |
EP1926554A2 (en) | 2008-06-04 |
RU2008102366A (ru) | 2009-07-27 |
CN101257973A (zh) | 2008-09-03 |
CN102786665A (zh) | 2012-11-21 |
CN101257973B (zh) | 2014-07-30 |
US20060293172A1 (en) | 2006-12-28 |
US8048819B2 (en) | 2011-11-01 |
KR101391784B1 (ko) | 2014-05-07 |
EP2283922A3 (en) | 2013-07-03 |
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