JP2023064723A - Conductive resin composition - Google Patents
Conductive resin composition Download PDFInfo
- Publication number
- JP2023064723A JP2023064723A JP2022169229A JP2022169229A JP2023064723A JP 2023064723 A JP2023064723 A JP 2023064723A JP 2022169229 A JP2022169229 A JP 2022169229A JP 2022169229 A JP2022169229 A JP 2022169229A JP 2023064723 A JP2023064723 A JP 2023064723A
- Authority
- JP
- Japan
- Prior art keywords
- conductive
- acid
- resin composition
- conductive resin
- epoxy resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 154
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 148
- 239000003822 epoxy resin Substances 0.000 claims abstract description 147
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 100
- -1 organic acid compound Chemical class 0.000 claims abstract description 85
- 150000003573 thiols Chemical class 0.000 claims abstract description 48
- 239000000853 adhesive Substances 0.000 claims abstract description 44
- 230000001070 adhesive effect Effects 0.000 claims abstract description 44
- 239000000463 material Substances 0.000 claims abstract description 44
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 33
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical class C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 59
- 229920005989 resin Polymers 0.000 claims description 55
- 239000011347 resin Substances 0.000 claims description 55
- 239000007788 liquid Substances 0.000 claims description 13
- 239000004593 Epoxy Substances 0.000 claims description 12
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000004844 aliphatic epoxy resin Substances 0.000 claims description 6
- 239000000758 substrate Substances 0.000 abstract description 41
- 238000001723 curing Methods 0.000 description 117
- 238000000576 coating method Methods 0.000 description 48
- 239000011248 coating agent Substances 0.000 description 46
- 238000000034 method Methods 0.000 description 30
- 239000000843 powder Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 28
- 239000003963 antioxidant agent Substances 0.000 description 25
- 235000006708 antioxidants Nutrition 0.000 description 25
- 239000000976 ink Substances 0.000 description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 19
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 16
- 229910052709 silver Inorganic materials 0.000 description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 239000004332 silver Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 238000009413 insulation Methods 0.000 description 12
- 238000007639 printing Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000002966 varnish Substances 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- 230000003078 antioxidant effect Effects 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 238000000465 moulding Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000007650 screen-printing Methods 0.000 description 8
- 229930185605 Bisphenol Natural products 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000000470 constituent Substances 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229910001385 heavy metal Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000003607 modifier Substances 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 238000009736 wetting Methods 0.000 description 7
- 239000000080 wetting agent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- 229910000679 solder Inorganic materials 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000006078 metal deactivator Substances 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 229920002732 Polyanhydride Polymers 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000012847 fine chemical Substances 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 238000000518 rheometry Methods 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
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- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- HECGKCOICWUUJU-UHFFFAOYSA-N bis(diphenylphosphanylmethyl)-phenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 HECGKCOICWUUJU-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000007646 gravure printing Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
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- ZNAMMSOYKPMPGC-HTOAHKCRSA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-(2-phenylethylsulfanyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1SCCC1=CC=CC=C1 ZNAMMSOYKPMPGC-HTOAHKCRSA-N 0.000 description 2
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
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- 101001057956 Homo sapiens 55 kDa erythrocyte membrane protein Proteins 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- LGOPTUPXVVNJFH-UHFFFAOYSA-N pentadecanethioic s-acid Chemical compound CCCCCCCCCCCCCCC(O)=S LGOPTUPXVVNJFH-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- CUQCMXFWIMOWRP-UHFFFAOYSA-N phenyl biguanide Chemical compound NC(N)=NC(N)=NC1=CC=CC=C1 CUQCMXFWIMOWRP-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- CCDXIADKBDSBJU-UHFFFAOYSA-N phenylmethanetriol Chemical group OC(O)(O)C1=CC=CC=C1 CCDXIADKBDSBJU-UHFFFAOYSA-N 0.000 description 1
- GXYJVHVZCMHHFY-UHFFFAOYSA-N phosphane;tetrabutylphosphanium Chemical class P.CCCC[P+](CCCC)(CCCC)CCCC GXYJVHVZCMHHFY-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- MGNVWUDMMXZUDI-UHFFFAOYSA-N propane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CCCS(O)(=O)=O MGNVWUDMMXZUDI-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011134 resol-type phenolic resin Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MXNUCYGENRZCBO-UHFFFAOYSA-M sodium;ethene;2-methylprop-2-enoate Chemical compound [Na+].C=C.CC(=C)C([O-])=O MXNUCYGENRZCBO-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- RYTMIGZBRFDNMS-UHFFFAOYSA-N sulfonylmethylphosphonic acid Chemical compound OP(O)(=O)C=S(=O)=O RYTMIGZBRFDNMS-UHFFFAOYSA-N 0.000 description 1
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HLNHDVOODYDVRZ-UHFFFAOYSA-M tetraphenylphosphanium;acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HLNHDVOODYDVRZ-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- AEFPPQGZJFTXDR-UHFFFAOYSA-M tetraphenylphosphanium;iodide Chemical compound [I-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEFPPQGZJFTXDR-UHFFFAOYSA-M 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Conductive Materials (AREA)
- Non-Insulated Conductors (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
本発明は、導電性樹脂組成物に関する。また、本発明は、導電膜、基材にスクリーン印刷等により回路等を形成する際に用いられる導電性インク、接着対象部位を導電性を有するように接着するために用いられる導電性接着剤、及び電子部品を回路基板等に導電接続する際に用いられる回路接続材料に関する。 The present invention relates to a conductive resin composition. In addition, the present invention provides a conductive film, a conductive ink used when forming a circuit or the like on a base material by screen printing or the like, a conductive adhesive used for bonding the adhesion target part so that it has conductivity, and a circuit-connecting material used for conductively connecting an electronic component to a circuit board or the like.
導電性樹脂組成物としては、多種多様な組成のものが知られており、導電性ペースト、導電膜、導電性インク、導電性塗料、回路接続材料、導電性接着剤等として、電子回路の形成、電子部品の接着等の種々の用途に使用されている。
例えば、導電回路や電極等の導電構造を形成するために有用な導電性を有する膜が求められている。
例えば、各種の印刷方法に適用可能であり、相互接続及びトレース、電極等の導電構造を有するフレキシブルプラスチック基材、フィルム基材、シート基材、樹脂成型品、ガラス、ガラスエポキシ、セラミック基材等の製造に有用な導電性インクが求められている。
例えば、コンピュータや携帯電話等の電子機器において、LED素子、半導体素子、コンデンサ等の各種の電子部品を同一回路基板上に高密度実装し高集積化するための回路接続材料が求められている。
A wide variety of compositions are known as conductive resin compositions, and are used as conductive pastes, conductive films, conductive inks, conductive paints, circuit connection materials, conductive adhesives, etc. to form electronic circuits. , and is used for various purposes such as adhesion of electronic parts.
For example, there is a need for conductive films that are useful for forming conductive structures such as conductive circuits and electrodes.
For example, flexible plastic substrates, film substrates, sheet substrates, resin molded products, glass, glass epoxy, ceramic substrates, etc., which are applicable to various printing methods and have conductive structures such as interconnects, traces, and electrodes. There is a need for conductive inks useful in the manufacture of.
For example, in electronic devices such as computers and mobile phones, there is a demand for circuit connection materials for high-density mounting and high integration of various electronic components such as LED elements, semiconductor elements and capacitors on the same circuit board.
これまで、導電性樹脂組成物としては、樹脂と導電性粒子を含む導電性樹脂組成物(導電性ペースト)が知られている。しかし、導電性樹脂組成物は、体積抵抗率が十分に低くならず、低い体積抵抗率が求められる用途とする場合には、導電性粒子として銀粒子を用いる必要があった。また、導電性樹脂組成物から得られる膜の体積抵抗率を低くするために、導電性粒子を大量に含有させた場合には、各種基材に対する膜の密着性(接合強度)が低下し、満足できるものではなかった。
特許文献1には、導電性粉末が少なくとも銀を用いた銀系粉末であり、樹脂成分が熱硬化性樹脂及び熱可塑性樹脂の少なくとも一方であり、さらに、特定の分子量及び構造を有するエステル系化合物又はその塩、あるいは、エーテル/アミン系化合物を含有する、導電性ペースト組成物が開示されている。
A conductive resin composition (conductive paste) containing a resin and conductive particles has been known as a conductive resin composition. However, the conductive resin composition does not have a sufficiently low volume resistivity, and silver particles have to be used as the conductive particles for applications that require a low volume resistivity. In addition, when a large amount of conductive particles are contained in order to lower the volume resistivity of the film obtained from the conductive resin composition, the adhesion (bonding strength) of the film to various substrates decreases, was not satisfactory.
In Patent Document 1, the conductive powder is a silver-based powder using at least silver, the resin component is at least one of a thermosetting resin and a thermoplastic resin, and an ester-based compound having a specific molecular weight and structure or a salt thereof, or a conductive paste composition containing an ether/amine compound.
しかし、銀粒子は、非常に高価でコスト的に不利であり、一方で、銀粒子以外の導電性粒子を用いた場合には、導電性樹脂組成物の膜の体積抵抗率が高くなり導電性が不十分になることがあった。また、体積抵抗率を低くするために導電性粒子を大量に含有させた場合には、各種基材に対する密着性が不十分になることがあった。
これまで、導電膜を形成した際の体積抵抗率が低く、良好な導電性を示し、各種基材に対する密着性(接合強度)が優れる導電性樹脂組成物は知られていなかった。
However, silver particles are very expensive and disadvantageous in terms of cost. was sometimes insufficient. Moreover, when a large amount of conductive particles are contained in order to lower the volume resistivity, the adhesion to various substrates may become insufficient.
Until now, there has been no known conductive resin composition that exhibits low volume resistivity when formed into a conductive film, exhibits good conductivity, and exhibits excellent adhesion (bonding strength) to various substrates.
本発明が解決しようとする課題は、良好な導電性を示し、各種基材に対する密着性(接合強度)が優れ、導電性インク、導電性接着剤、回路接続材料等として有用な導電性樹脂組成物を提供することである。さらに、当該導電性樹脂組成物から形成された導電膜、当該導電性樹脂組成物を含む導電性インク、当該導電性樹脂組成物を含む導電性接着剤、及び、当該導電性樹脂組成物を含む回路接続材料を提供することである。 The problem to be solved by the present invention is a conductive resin composition that exhibits good conductivity, has excellent adhesion (bonding strength) to various substrates, and is useful as a conductive ink, a conductive adhesive, a circuit connection material, etc. It is to provide things. Furthermore, a conductive film formed from the conductive resin composition, a conductive ink containing the conductive resin composition, a conductive adhesive containing the conductive resin composition, and the conductive resin composition It is to provide a circuit connecting material.
本発明者は、上記課題を解決すべく鋭意検討を行った結果、特定の組成の導電性樹脂組成物とすることで、上記課題が解決できることを見出し、本発明を完成するに至った。
具体的には、以下に示すとおりである。
項1:(a)錫粉末、(b)エポキシ樹脂、(c)有機酸化合物及び(d)チオール系硬化剤、
を含む、導電性樹脂組成物。
項2:(b)エポキシ樹脂が、
(i)25℃で液状である、及び/又は、
(ii)ビスフェノール型エポキシ樹脂、ゴム変性エポキシ樹脂、脂環式エポキシ樹脂、グリシジルアミン型エポキシ樹脂、ウレタン変性エポキシ樹脂、ポリサルファイド変性エポキシ樹脂、キレート変性エポキシ樹脂、トリスフェノールメタン型エポキシ樹脂、ナフタレン型エポキシ樹脂、ジシクロペンタジエン変性エポキシ樹脂、脂肪族エポキシ樹脂、ポリエーテル変性エポキシ樹脂、多官能芳香族エポキシ樹脂及び水素添加ビスフェノール型エポキシ樹脂からなる群より選ばれる少なくとも1種である、項1に記載の導電性樹脂組成物。
項3:項1又は2に記載の導電性樹脂組成物から形成された、体積抵抗率が1.0×10-2Ω・cm未満である導電膜。
項4:項1又は2に記載の導電性樹脂組成物を含む、導電性インク。
項5:項1又は2に記載の導電性樹脂組成物を含む、導電性接着剤。
項6:項1又は2に記載の導電性樹脂組成物を含む、回路接続材料。
As a result of intensive studies to solve the above problems, the present inventors have found that the above problems can be solved by using a conductive resin composition having a specific composition, and have completed the present invention.
Specifically, it is as shown below.
Item 1: (a) tin powder, (b) epoxy resin, (c) organic acid compound and (d) thiol-based curing agent,
A conductive resin composition comprising:
Item 2: (b) the epoxy resin is
(i) liquid at 25° C. and/or
(ii) bisphenol-type epoxy resin, rubber-modified epoxy resin, alicyclic epoxy resin, glycidylamine-type epoxy resin, urethane-modified epoxy resin, polysulfide-modified epoxy resin, chelate-modified epoxy resin, trisphenolmethane-type epoxy resin, naphthalene-type epoxy Item 2. Item 1. The resin is at least one selected from the group consisting of resins, dicyclopentadiene-modified epoxy resins, aliphatic epoxy resins, polyether-modified epoxy resins, polyfunctional aromatic epoxy resins, and hydrogenated bisphenol-type epoxy resins. A conductive resin composition.
Item 3: A conductive film formed from the conductive resin composition according to Item 1 or 2 and having a volume resistivity of less than 1.0×10 −2 Ω·cm.
Item 4: A conductive ink comprising the conductive resin composition according to Item 1 or 2.
Item 5: A conductive adhesive comprising the conductive resin composition according to Item 1 or 2.
Item 6: A circuit-connecting material comprising the conductive resin composition according to Item 1 or 2.
本発明により、良好な導電性を示し、各種基材に対する密着性(接合強度)が優れ、導電性インク、導電性接着剤、回路接続材料等として有用な導電性樹脂組成物が提供される。
本発明の導電性樹脂組成物は、プリンテッドエレクトロニクス材料として有用であり、表示装置、車両関連部品、IoT、移動通信システム(Mobile Communication System)等の各種電子機器等の大量生産に際して極めて有用である。
INDUSTRIAL APPLICABILITY The present invention provides a conductive resin composition that exhibits good conductivity, has excellent adhesion (bonding strength) to various substrates, and is useful as a conductive ink, a conductive adhesive, a circuit connecting material, and the like.
INDUSTRIAL APPLICABILITY The conductive resin composition of the present invention is useful as a printed electronics material, and is extremely useful in the mass production of various electronic devices such as display devices, vehicle-related parts, IoT, and mobile communication systems. .
本発明は、導電性樹脂組成物、導電膜、導電性インク、導電性接着剤及び回路接続材料に係るものである。以下、これらについて詳細に説明する。 TECHNICAL FIELD The present invention relates to a conductive resin composition, a conductive film, a conductive ink, a conductive adhesive, and a circuit connecting material. These will be described in detail below.
[導電性樹脂組成物]
<(a)錫粉末>
本発明の導電性樹脂組成物が含む錫粉末は、錫99.5質量%以上と不可避不純物から構成される粉末である。
錫粉末における錫の含有率は、蛍光X線分析(XRF)装置等を用いることで容易に測定できる。
錫粉末に含まれる不可避不純物としては、例えば、Mn、Sb、Si、K、Na、Li、Ba、Sr、Ca、Mg、Be、Zn、Pb、Cd、Tl、V、Al、Zr、W、Mo、Ti、Co、Ag、Cu、Ni、Au、B、C、N、O、Ge、Sb、In、As、Al、Fe等からなる群より選ばれる1種以上の他の原子が挙げられる。
他の原子の含有率は、好ましくは錫粉末中0.3質量%未満、より好ましくは0.1質量%以下である。
[Conductive resin composition]
<(a) Tin powder>
The tin powder contained in the conductive resin composition of the present invention is powder composed of 99.5% by mass or more of tin and unavoidable impurities.
The content of tin in the tin powder can be easily measured using an X-ray fluorescence spectrometer (XRF) or the like.
Examples of inevitable impurities contained in the tin powder include Mn, Sb, Si, K, Na, Li, Ba, Sr, Ca, Mg, Be, Zn, Pb, Cd, Tl, V, Al, Zr, W, One or more other atoms selected from the group consisting of Mo, Ti, Co, Ag, Cu, Ni, Au, B, C, N, O, Ge, Sb, In, As, Al, Fe, etc. .
The content of other atoms is preferably less than 0.3% by mass, more preferably 0.1% by mass or less in the tin powder.
錫粉末の形状は、特に限定されない。例えば、鱗片状(フレーク状)、扁平状、真球状、略球状(例えば、縦横のアスペクト比が1.5以下)、ブロック状、板状、多角錐状、多面体状、棒状、繊維状、針状、不定形状等のものを、用途等に応じて用いることができる。本発明においては、体積抵抗率、分散性、取扱性等の観点から、鱗片状、真球状、略球状、扁平状、不定形状のものが好ましい。 The shape of the tin powder is not particularly limited. For example, scale-like (flake-like), flattened, spherical, substantially spherical (e.g., vertical and horizontal aspect ratio of 1.5 or less), block-like, plate-like, polygonal pyramid-like, polyhedral-like, rod-like, fibrous, needle-like Shapes, irregular shapes, etc. can be used depending on the application. In the present invention, from the viewpoint of volume resistivity, dispersibility, handleability, etc., scaly, spherical, substantially spherical, flattened, and irregularly shaped particles are preferred.
球状又は不定形状の錫粉末の体積平均粒子径(体積基準粒度分布における累積頻度%径の50%粒子径D50)は、特に制限されない。D50としては、例えば0.5μm以上、好ましくは1.0μm以上、より好ましくは3.0μm以上であり、例えば300μm以下、好ましくは200μm以下、より好ましくは100μm以下である。D50が0.5μm以上であると、錫粉末の分散性及び取扱性が良好になる。D50が300μm以下であると、体積抵抗率を低くでき、分散性及び取扱性が良好になる。 The volume average particle size (50% particle size D50 of the cumulative frequency % size in the volume-based particle size distribution) of the spherical or amorphous tin powder is not particularly limited. D50 is, for example, 0.5 μm or more, preferably 1.0 μm or more, more preferably 3.0 μm or more, and is, for example, 300 μm or less, preferably 200 μm or less, more preferably 100 μm or less. When D50 is 0.5 µm or more, the dispersibility and handleability of the tin powder are improved. When the D50 is 300 µm or less, the volume resistivity can be lowered, and the dispersibility and handleability are improved.
扁平状又は鱗片状の錫粉末の平均直径、平均厚及びアスペクト比(平均直径/平均厚)は、特に限定されない。
平均直径は、例えば0.5μm以上、好ましくは1.0μm以上、より好ましくは5.0μm以上であり、例えば500.0μm以下、好ましくは300.0μm以下、より好ましくは150.0μm以下である。
平均厚は、例えば、0.1μm以上、好ましくは0.5μm以上、より好ましくは1.0μm以上であり、例えば50.0μm以下、好ましくは20.0μm以下、より好ましくは10.0μm以下である。
アスペクト比は、例えば、2以上、好ましくは10以上、より好ましくは50以上である。
The average diameter, average thickness and aspect ratio (average diameter/average thickness) of the flat or scale-like tin powder are not particularly limited.
The average diameter is, for example, 0.5 μm or more, preferably 1.0 μm or more, more preferably 5.0 μm or more, and for example, 500.0 μm or less, preferably 300.0 μm or less, more preferably 150.0 μm or less.
The average thickness is, for example, 0.1 μm or more, preferably 0.5 μm or more, more preferably 1.0 μm or more, and is, for example, 50.0 μm or less, preferably 20.0 μm or less, more preferably 10.0 μm or less. .
The aspect ratio is, for example, 2 or more, preferably 10 or more, more preferably 50 or more.
導電性樹脂組成物における、(a)錫粉末の含有量は、特に限定されない。導電性樹脂組成物の導電性等の観点から適宜定めることができる。例えば、(a)錫粉末、(b)エポキシ樹脂、(c)有機酸化合物及び(d)チオール系硬化剤の合計量を100質量%として、50.0質量%以上、好ましくは60.0質量%以上、より好ましくは85.0質量%以上、さらに好ましくは88.0質量%以上、よりさらに好ましくは92.0質量%以上であり、例えば98.0質量%以下、好ましくは97.0質量%以下である。
(a)錫粉末、(b)エポキシ樹脂、(c)有機酸化合物及び(d)チオール系硬化剤の合計量100質量%における(a)錫粉末の含有量が50.0質量%未満であると、導電性が低下し、体積抵抗率が上昇する又は実施例に記載するLED点灯試験でLEDが点灯しないおそれがあり、98.0質量%を超えると、塗膜の接合強度が低下するおそれがある。
The content of (a) tin powder in the conductive resin composition is not particularly limited. It can be determined as appropriate from the viewpoint of the conductivity of the conductive resin composition. For example, when the total amount of (a) tin powder, (b) epoxy resin, (c) organic acid compound and (d) thiol-based curing agent is 100% by mass, it is 50.0% by mass or more, preferably 60.0% by mass. % or more, more preferably 85.0 mass % or more, still more preferably 88.0 mass % or more, still more preferably 92.0 mass % or more, for example 98.0 mass % or less, preferably 97.0 mass % % or less.
The content of (a) tin powder is less than 50.0% by mass based on 100% by mass of the total amount of (a) tin powder, (b) epoxy resin, (c) organic acid compound and (d) thiol-based curing agent. If it exceeds 98.0 mass%, the bonding strength of the coating film may decrease. There is
<(b)エポキシ樹脂>
エポキシ樹脂としては、分子構造中にエポキシ基を2つ以上有するモノマー、オリゴマー、ポリマー全般を用いることができ、その分子量や分子構造は特に限定されない。本実施形態で用いられるエポキシ樹脂としては、例えば、ビフェニル型エポキシ樹脂;ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、テトラメチルビスフェノールF型エポキシ樹脂、プロピレンオキシド付加ビスフェノール型エポキシ樹脂等のビスフェノール型エポキシ樹脂;アルキレンオキサイド変性ビスフェノール型樹脂;ナフタレン型エポキシ樹脂;キレート変性エポキシ樹脂;スチルベン型エポキシ樹脂;フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂等のノボラック型エポキシ樹脂;トリスフェノールメタン型エポキシ樹脂、アルキル変性トリスフェノールメタン型エポキシ樹脂等の多官能エポキシ樹脂;フェニレン骨格を有するフェノールアラルキル型エポキシ樹脂、ビフェニレン骨格を有するフェノールアラルキル型エポキシ樹脂等のアラルキル型エポキシ樹脂;ジヒドロキシナフタレン型エポキシ樹脂、ジヒドロキシナフタレンの2量体をグリシジルエーテル化して得られるエポキシ樹脂等のナフトール型エポキシ樹脂;トリグリシジルイソシアヌレート、モノアリルジグリシジルイソシアヌレート等のトリアジン核含有エポキシ樹脂;イソシアネート基を有するウレタン結合含有化合物とヒドロキシ基含有エポキシ化合物とを反応させて得られる樹脂等のウレタン変性エポキシ樹脂;ジシクロペンタジエン変性エポキシ樹脂等の有橋環状炭化水素化合物変性フェノール型エポキシ樹脂;ダイマー酸変性エポキシ樹脂;ゴム変性エポキシ樹脂;ポリサルファイド変性エポキシ樹脂;グリシジルアミン型エポキシ樹脂;グリシジルエステル型エポキシ樹脂;等が挙げられる。また、エポキシ樹脂としては、例えば、エポキシ基を分子構造中に2つ以上含む化合物のうちの、ビスフェノールA、ビスフェノールF、ビフェノール等のビスフェノール化合物又はこれらの誘導体、水素添加ビスフェノールA、水素添加ビスフェノールF、水素添加ビフェノール、シクロヘキサンジオール、シクロヘキサンジメタノール、シクロヘキサンジエタノール等の脂環構造を有するポリオール又はこれらの誘導体のエポキシ化物等の脂環式エポキシ樹脂;ブタンジオール、ヘキサンジオール、オクタンジオール、ノナンジオール、デカンジオール、ポリブタジエンポリオール等の脂肪族ポリオール又はこれらの誘導体のエポキシ化物等の脂肪族エポキシ樹脂;トリヒドロキシフェニルメタン骨格(トリスフェノールメタン骨格)を有するエポキシ樹脂;アミノフェノール型エポキシ樹脂等;ポリエーテル変性エポキシ樹脂;多官能芳香族エポキシ樹脂;水素添加ビスフェノール型エポキシ樹脂等が挙げられる。エポキシ樹脂は、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。
<(b) epoxy resin>
As the epoxy resin, all monomers, oligomers, and polymers having two or more epoxy groups in the molecular structure can be used, and the molecular weight and molecular structure are not particularly limited. Epoxy resins used in the present embodiment include, for example, biphenyl-type epoxy resins; Resin; alkylene oxide-modified bisphenol type resin; naphthalene type epoxy resin; chelate-modified epoxy resin; stilbene type epoxy resin; polyfunctional epoxy resins such as modified trisphenolmethane type epoxy resins; aralkyl type epoxy resins such as phenol aralkyl type epoxy resins having a phenylene skeleton and phenol aralkyl type epoxy resins having a biphenylene skeleton; dihydroxynaphthalene type epoxy resins, dihydroxynaphthalene; naphthol-type epoxy resins such as epoxy resins obtained by glycidyl-etherifying a monomer; triazine nucleus-containing epoxy resins such as triglycidyl isocyanurate and monoallyl diglycidyl isocyanurate; urethane bond-containing compounds having isocyanate groups and hydroxyl group-containing epoxies Urethane-modified epoxy resins such as resins obtained by reacting compounds; bridged cyclic hydrocarbon compound-modified phenolic epoxy resins such as dicyclopentadiene-modified epoxy resins; dimer acid-modified epoxy resins; rubber-modified epoxy resins; polysulfide-modified epoxy Resin; glycidylamine type epoxy resin; glycidyl ester type epoxy resin; and the like. Examples of epoxy resins include, among compounds containing two or more epoxy groups in the molecular structure, bisphenol compounds such as bisphenol A, bisphenol F, and biphenol, or derivatives thereof, hydrogenated bisphenol A, and hydrogenated bisphenol F. , Hydrogenated biphenol, cyclohexanediol, cyclohexanedimethanol, cyclohexanediethanol, polyols having an alicyclic structure, or epoxidized derivatives of these alicyclic epoxy resins; butanediol, hexanediol, octanediol, nonanediol, decane Aliphatic epoxy resins such as diols, aliphatic polyols such as polybutadiene polyol, or epoxidized derivatives thereof; epoxy resins having a trihydroxyphenylmethane skeleton (trisphenolmethane skeleton); aminophenol type epoxy resins, etc.; polyether-modified epoxy Resins; polyfunctional aromatic epoxy resins; hydrogenated bisphenol type epoxy resins and the like. An epoxy resin may be used individually by 1 type, and may be used in combination of 2 or more types.
本発明の導電性樹脂組成物は、密着性、耐熱性、作業性、取扱性等をより効果的に向上させる観点から、(b)エポキシ樹脂が、
(i)25℃で液状である、及び/又は、
(ii)ビスフェノール型エポキシ樹脂、ゴム変性エポキシ樹脂、脂環式エポキシ樹脂、グリシジルアミン型エポキシ樹脂、ウレタン変性エポキシ樹脂、ポリサルファイド変性エポキシ樹脂、キレート変性エポキシ樹脂、トリスフェノールメタン型エポキシ樹脂、ナフタレン型エポキシ樹脂、ジシクロペンタジエン変性エポキシ樹脂、脂肪族ポリオール又はこれらの誘導体のエポキシ化物等の脂肪族エポキシ樹脂、ポリエーテル変性エポキシ樹脂、多官能芳香族エポキシ樹脂及び水素添加ビスフェノール型エポキシ樹脂からなる群より選ばれる少なくとも1種であることがより好ましい。
25℃において液状のエポキシ樹脂としては、例えば、ビスフェノール型エポキシ樹脂、ナフタレン型エポキシ樹脂;グリシジルエステル型エポキシ樹脂、グリシジルアミン型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、エステル骨格を有する脂環式エポキシ樹脂等の脂環式エポキシ樹脂、シクロヘキサン型エポキシ樹脂、シクロヘキサンジメタノール型エポキシ樹脂、グリシジルアミン型エポキシ樹脂、ポリブタジエンポリオールのエポキシ化物であるエポキシ樹脂、ゴム変性エポキシ樹脂、キレート変性エポキシ樹脂、ウレタン変性エポキシ樹脂、ポリサルファイド変性エポキシ樹脂、トリスフェノールメタン型エポキシ樹脂、ジシクロペンタジエン変性エポキシ樹脂、脂肪族ポリオール又はこれらの誘導体のエポキシ化物等の脂肪族エポキシ樹脂、ポリエーテル変性エポキシ樹脂、多官能芳香族エポキシ樹脂、水素添加ビスフェノール型エポキシ樹脂等が挙げられる。好ましくは、ビスフェノール型エポキシ樹脂、ゴム変性エポキシ樹脂、脂環式エポキシ樹脂、グリシジルアミン型エポキシ樹脂、ウレタン変性エポキシ樹脂、ポリサルファイド変性エポキシ樹脂、キレート変性エポキシ樹脂、トリスフェノールメタン型エポキシ樹脂、ナフタレン型エポキシ樹脂、ジシクロペンタジエン変性エポキシ樹脂、脂肪族ポリオール又はこれらの誘導体のエポキシ化物等の脂肪族エポキシ樹脂、ポリエーテル変性エポキシ樹脂、多官能芳香族エポキシ樹脂、水素添加ビスフェノール型エポキシ樹脂からなる群より選ばれる1種以上がより好ましい。
具体例としては、例えば、三菱ケミカル社製のjER807、jER828、jER828US、jER828EL、jER825、jER630、jER630LSD等;ADEKA社製のアデカレジンEP-4100、アデカレジンEP-4300E、アデカレジンEP-4400、アデカレジンEP-4901E、アデカレジンEP-4000、アデカレジンEP-4000S、アデカレジンEP-4005、アデカレジンEPU-6、アデカレジンEPU-1395、アデカレジンEPU-73B、アデカレジンEPU-17、アデカレジンEPU-11F、アデカレジンEPR-1415-1、アデカレジンEPU-15F、アデカレジンEPR-2000、アデカレジンEPR-2007、アデカレジンEP-49-10N、アデカレジンEP-49-10P2、アデカレジンEP-49-23、アデカグリシロールED-503、アデカグリシロールED-503G、アデカグリシロールED-506、アデカグリシロールED-523T、アデカグリシロールED-505等;東レファインケミカル社製のFLEP-50、FLEP-60等;共栄社化学社製のエポライト40E、エポライト100E、エポライト200E、エポライト400E、エポライト70P、エポライト200P、エポライト400P、エポライト1500NP、エポライト1600、エポライト80MF、エポライト4000、エポライト3002(N)等;ナガセケムテックス社製のデナコールEX-201、デナコールEX-201-IM、デナコールEX-252、デナコールEX-991L等が挙げられる。これらは、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
これらの中でも、得られる導電性樹脂組成物の密着性、耐熱性、作業性及び取扱性等の観点から、ビスフェノール型エポキシ樹脂、ゴム変性エポキシ樹脂、脂環式エポキシ樹脂、グリシジルアミン型エポキシ樹脂、ウレタン変性エポキシ樹脂、キレート変性エポキシ樹脂、ポリサルファイド変性エポキシ樹脂、トリスフェノールメタン型エポキシ樹脂、ナフタレン型エポキシ樹脂及びジシクロペンタジエン変性エポキシ樹脂を含むことが好ましい。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。
In the conductive resin composition of the present invention, from the viewpoint of more effectively improving adhesion, heat resistance, workability, handleability, etc., (b) an epoxy resin is
(i) liquid at 25° C. and/or
(ii) bisphenol-type epoxy resin, rubber-modified epoxy resin, alicyclic epoxy resin, glycidylamine-type epoxy resin, urethane-modified epoxy resin, polysulfide-modified epoxy resin, chelate-modified epoxy resin, trisphenolmethane-type epoxy resin, naphthalene-type epoxy selected from the group consisting of resins, dicyclopentadiene-modified epoxy resins, aliphatic epoxy resins such as epoxidized products of aliphatic polyols or derivatives thereof, polyether-modified epoxy resins, polyfunctional aromatic epoxy resins and hydrogenated bisphenol type epoxy resins It is more preferable that it is at least one kind.
Examples of epoxy resins that are liquid at 25° C. include bisphenol-type epoxy resins, naphthalene-type epoxy resins; glycidyl ester-type epoxy resins, glycidylamine-type epoxy resins, phenol novolac-type epoxy resins, alicyclic epoxy resins having an ester skeleton, and the like. cyclohexane-type epoxy resin, cyclohexanedimethanol-type epoxy resin, glycidylamine-type epoxy resin, epoxy resin that is an epoxidized product of polybutadiene polyol, rubber-modified epoxy resin, chelate-modified epoxy resin, urethane-modified epoxy resin, Aliphatic epoxy resins such as polysulfide-modified epoxy resins, trisphenolmethane-type epoxy resins, dicyclopentadiene-modified epoxy resins, epoxidized products of aliphatic polyols or their derivatives, polyether-modified epoxy resins, polyfunctional aromatic epoxy resins, hydrogen Additive bisphenol type epoxy resins and the like can be mentioned. Preferably, bisphenol-type epoxy resin, rubber-modified epoxy resin, alicyclic epoxy resin, glycidylamine-type epoxy resin, urethane-modified epoxy resin, polysulfide-modified epoxy resin, chelate-modified epoxy resin, trisphenolmethane-type epoxy resin, naphthalene-type epoxy selected from the group consisting of resins, dicyclopentadiene-modified epoxy resins, aliphatic epoxy resins such as epoxidized products of aliphatic polyols or derivatives thereof, polyether-modified epoxy resins, polyfunctional aromatic epoxy resins, and hydrogenated bisphenol type epoxy resins more preferably one or more.
Specific examples include jER807, jER828, jER828US, jER828EL, jER825, jER630, jER630LSD, etc. manufactured by Mitsubishi Chemical; , ADEKA RESIN EP-4000, ADEKA RESIN EP-4000S, ADEKA RESIN EP-4005, ADEKA RESIN EPU-6, ADEKA RESIN EPU-1395, ADEKA RESIN EPU-73B, ADEKA RESIN EPU-17, ADEKA RESIN EPU-11F, ADEKA RESIN EPR-1415-1, ADEKA RESIN EPU -15F, ADEKA RESIN EPR-2000, ADEKA RESIN EPR-2007, ADEKA RESIN EP-49-10N, ADEKA RESIN EP-49-10P2, ADEKA RESIN EP-49-23, ADEKA GLYCIROL ED-503, ADEKA GLYCIROL ED-503G, ADEKA GLYCI Roll ED-506, ADEKA GLYCIROL ED-523T, ADEKA GLYCIROL ED-505, etc.; FLEP-50, FLEP-60, etc. manufactured by Toray Fine Chemicals Co., Ltd.; , Epolite 70P, Epolite 200P, Epolite 400P, Epolite 1500NP, Epolite 1600, Epolite 80MF, Epolite 4000, Epolite 3002 (N), etc.; 252, Denacol EX-991L and the like. These may be used individually by 1 type, and may be used in combination of 2 or more type.
Among these, from the viewpoint of adhesiveness, heat resistance, workability and handleability of the resulting conductive resin composition, bisphenol type epoxy resin, rubber modified epoxy resin, alicyclic epoxy resin, glycidylamine type epoxy resin, It preferably contains a urethane-modified epoxy resin, a chelate-modified epoxy resin, a polysulfide-modified epoxy resin, a trisphenolmethane-type epoxy resin, a naphthalene-type epoxy resin, and a dicyclopentadiene-modified epoxy resin. These may be used individually by 1 type, and may be used in combination of 2 or more types.
導電性樹脂組成物における、(b)エポキシ樹脂の含有量は、特に限定されない。(a)錫粉末、(b)エポキシ樹脂、(c)有機酸化合物及び(d)チオール系硬化剤の合計量を100質量%として、例えば0.5質量%以上、好ましくは1.0質量%以上、より好ましくは1.5質量%以上であり、例えば25.0質量%以下、好ましくは20.0質量%以下、より好ましくは15.0質量%以下、さらに好ましくは10.0質量%以下である。
(a)錫粉末、(b)エポキシ樹脂、(c)有機酸化合物及び(d)チオール系硬化剤の合計量100質量%における(b)エポキシ樹脂の含有量が0.5質量%未満であると、膜形成ができなくなるおそれがあり、塗膜の接合強度が低下するおそれがあり、25.0質量%を超えると導電性が低下し、体積抵抗率が上昇する又は実施例に記載するLED点灯試験でLEDが点灯しないおそれがある。
The content of (b) the epoxy resin in the conductive resin composition is not particularly limited. When the total amount of (a) tin powder, (b) epoxy resin, (c) organic acid compound and (d) thiol-based curing agent is 100% by mass, for example 0.5% by mass or more, preferably 1.0% by mass Above, more preferably 1.5% by mass or more, for example 25.0% by mass or less, preferably 20.0% by mass or less, more preferably 15.0% by mass or less, further preferably 10.0% by mass or less is.
The content of (b) epoxy resin is less than 0.5% by mass based on 100% by mass of the total amount of (a) tin powder, (b) epoxy resin, (c) organic acid compound and (d) thiol-based curing agent. If it exceeds 25.0% by mass, the conductivity decreases and the volume resistivity increases, or the LED described in the examples There is a possibility that the LED may not light up in the lighting test.
<(c)有機酸化合物>
有機酸化合物としては、例えば、R-Xn(式中、Rは、水素、炭素数1~50の有機基であり、Xは酸基であって複数のXは互いに異なっていてもよく、nは1以上の整数である。)で表される有機酸化合物の1種又は2種以上が挙げられる。
Xで表される酸基としては、例えば、カルボキシル基(-COOH)、スルホン酸基(-SO3H)、リン酸基(-PO4H2)等が挙げられる。
有機酸化合物としては、例えば、有機カルボン酸化合物、有機スルホン酸化合物、有機ホスホン酸化合物等からなる群より選ばれる1種以上が挙げられる。好ましくは、有機カルボン酸化合物である。
<(c) Organic acid compound>
Examples of organic acid compounds include R—X n (wherein R is hydrogen, an organic group having 1 to 50 carbon atoms, X is an acid group, and a plurality of Xs may be different from each other, n is an integer of 1 or more).
The acid group represented by X includes, for example, a carboxyl group (--COOH), a sulfonic acid group (--SO 3 H), a phosphoric acid group (--PO 4 H 2 ) and the like.
Examples of the organic acid compound include one or more selected from the group consisting of organic carboxylic acid compounds, organic sulfonic acid compounds, organic phosphonic acid compounds, and the like. Organic carboxylic acid compounds are preferred.
(有機カルボン酸化合物)
有機カルボン酸化合物は、分子構造中にカルボキシル基(-COOH)を1つ以上有する炭素数1~50の化合物であれば、特に限定されない。
有機カルボン酸化合物としては、例えば、ギ酸、酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクチル酸、ラウリン酸、ミリスチン酸、ペンタデシル酸、パルミチン酸、マルガリン酸、ステアリン酸、12-ヒドロキシステアリン酸、リシノール酸、オレイン酸、バクセン酸、リノール酸、リノレン酸、アラキジン酸、ベヘン酸、リグノセリン酸、セロチン酸、モンタン酸、メリシン酸、乳酸、グルコン酸、リンゴ酸、酒石酸、クエン酸、アビエチン酸、マロン酸、コハク酸、グルタル酸、アジピン酸、グルタコン酸、ピメリン酸、スベリン酸、アゼライン酸、2-メチルアゼライン酸、セバシン酸、デカン二酸ドデカン二酸、エイコ酸二酸、カプロン酸、エナント酸、カプリル酸、ペラルゴン酸、カプリン酸、ベヘン酸、アラキドン酸、エイコサペンタエン酸、ドコサヘキサエン酸、ドデセニルコハク酸、シトラコン酸、メサコン酸、イタコン酸、ジメチロールプロピオン酸、ジメチロールブタン酸、ジメチロール酪酸、ジメチロール吉草酸、トリメチロールプロパン酸、トリメチロールブタン酸、安息香酸、サリチル酸、ピルビン酸、パラメチル安息香酸、トルイル酸、4-エチル安息香酸、4-プロピル安息香酸、2-メチルプロパン酸、イソペンタン酸、2-エチルヘキサン酸、アクリル酸、メタクリル酸、プロピオル酸、クロトン酸、2-エチル-2-ブテン酸、マレイン酸、フマル酸、シュウ酸、ヘキサントリカルボン酸、シクロヘキシルカルボン酸、1,4-シクロヘキシルジカルボン酸、エチレンジアミン四酢酸、イソフタル酸、テレフタル酸、ナフタレンジカルボン酸、トリメリット酸、ピロメリット酸、パラストリン酸、イソピマール酸等からなる群より選ばれる1種以上が挙げられる。
さらに、炭素数が12以上の直鎖又は分岐鎖ジカルボン酸(例えば、岡村製油社製、SL-12、SL-20、UL-20、MMA-10R、SB-12、IPU-22、IPS-22、SB-20、UB-20等)も好適に用いることができる。
(Organic carboxylic acid compound)
The organic carboxylic acid compound is not particularly limited as long as it is a compound having 1 to 50 carbon atoms and having one or more carboxyl groups (--COOH) in its molecular structure.
Examples of organic carboxylic acid compounds include formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octylic acid, lauric acid, myristic acid, pentadecyl acid, palmitic acid, margaric acid, stearic acid, 12 - hydroxystearic acid, ricinoleic acid, oleic acid, vaccenic acid, linoleic acid, linolenic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid, montanic acid, melissic acid, lactic acid, gluconic acid, malic acid, tartaric acid, citric acid , abietic acid, malonic acid, succinic acid, glutaric acid, adipic acid, glutaconic acid, pimelic acid, suberic acid, azelaic acid, 2-methylazeleic acid, sebacic acid, decanedioic acid, dodecanedioic acid, eicoic diacid, capron acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, behenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid, dodecenylsuccinic acid, citraconic acid, mesaconic acid, itaconic acid, dimethylolpropionic acid, dimethylolbutanoic acid, dimethylol Butyric acid, dimethylolvaleric acid, trimethylolpropanoic acid, trimethylolbutanoic acid, benzoic acid, salicylic acid, pyruvic acid, paramethylbenzoic acid, toluic acid, 4-ethylbenzoic acid, 4-propylbenzoic acid, 2-methylpropanoic acid, isopentane acid, 2-ethylhexanoic acid, acrylic acid, methacrylic acid, propiolic acid, crotonic acid, 2-ethyl-2-butenoic acid, maleic acid, fumaric acid, oxalic acid, hexanetricarboxylic acid, cyclohexylcarboxylic acid, 1,4- One or more selected from the group consisting of cyclohexyldicarboxylic acid, ethylenediaminetetraacetic acid, isophthalic acid, terephthalic acid, naphthalenedicarboxylic acid, trimellitic acid, pyromellitic acid, parastric acid, isopimaric acid and the like.
Furthermore, linear or branched dicarboxylic acids having 12 or more carbon atoms (for example, manufactured by Okamura Oil Co., Ltd., SL-12, SL-20, UL-20, MMA-10R, SB-12, IPU-22, IPS-22 , SB-20, UB-20, etc.) can also be suitably used.
(有機スルホン酸化合物)
有機スルホン酸化合物は、分子構造中にスルホン酸基(-SO3H)を1つ以上有する化合物であれば、特に限定されない。
例えば、ベンゼンスルホン酸、n-ブチルベンゼンスルホン酸、n-オクチルベンゼンスルホン酸、n-ドデシルベンゼンスルホン酸、ペンタデシルベンゼンスルホン酸、2,5-ジメチルベンゼンスルホン酸、p-クロルベンゼンスルホン酸、2,5-ジクロロベンゼンスルホン酸、p-フェノールスルホン酸、クメンスルホン酸、キシレンスルホン酸、o-クレゾ-ルスルホン酸、m-クレゾ-ルスルホン酸、p-クレゾ-ルスルホン酸、p-トルエンスルホン酸、2-ナフタレンスルホン酸、1-ナフタレンスルホン酸、スチレンスルホン酸、4,4-ビフェニルジスルホン酸、アントラキノン-2-スルホン酸、m-ベンゼンジスルホン酸、アニリン-2,4-ジスルホン酸、アントラキノン-1,5-ジスルホン酸、ポリスチレンスルホン酸等の芳香族スルホン酸化合物;メタンスルホン酸、エタンスルホン酸、1-プロパンスルホン酸、n-オクチルスルホン酸、ペンタデシルスルホン酸、トリフルオロメタンスルホン酸、トリクロロメタンスルホン酸、1,2-エタンジスルホン酸、1,3-プロパンジスルホン酸、アミノメタンスルホン酸、2-アミノエタンスルホン酸等の脂肪族スルホン酸化合物;シクロペンタンスルホン酸、シクロヘキサンスルホン酸、3-シクロヘキシルアミノプロパンスルホン酸脂環族スルホン酸化合物等からなる群より選ばれる1種以上が挙げられる。
好ましくは、ベンゼンスルホン酸、ドデシルベンゼンスルホン酸、メタンスルホン酸、p-フェノールスルホン酸、p-トルエンスルホン酸及び(ポリ)スチレンスルホン酸等からなる群より選ばれる1種以上が挙げられる。
(Organic sulfonic acid compound)
The organic sulfonic acid compound is not particularly limited as long as it is a compound having one or more sulfonic acid groups (--SO 3 H) in its molecular structure.
For example, benzenesulfonic acid, n-butylbenzenesulfonic acid, n-octylbenzenesulfonic acid, n-dodecylbenzenesulfonic acid, pentadecylbenzenesulfonic acid, 2,5-dimethylbenzenesulfonic acid, p-chlorobenzenesulfonic acid, 2 , 5-dichlorobenzenesulfonic acid, p-phenolsulfonic acid, cumenesulfonic acid, xylenesulfonic acid, o-cresolsulfonic acid, m-cresolsulfonic acid, p-cresolsulfonic acid, p-toluenesulfonic acid, 2 -naphthalenesulfonic acid, 1-naphthalenesulfonic acid, styrenesulfonic acid, 4,4-biphenyldisulfonic acid, anthraquinone-2-sulfonic acid, m-benzenedisulfonic acid, aniline-2,4-disulfonic acid, anthraquinone-1,5 - aromatic sulfonic acid compounds such as disulfonic acid and polystyrene sulfonic acid; Aliphatic sulfonic acid compounds such as 1,2-ethanedisulfonic acid, 1,3-propanedisulfonic acid, aminomethanesulfonic acid and 2-aminoethanesulfonic acid; cyclopentanesulfonic acid, cyclohexanesulfonic acid, 3-cyclohexylaminopropanesulfone One or more selected from the group consisting of acid alicyclic sulfonic acid compounds and the like can be mentioned.
Preferably, one or more selected from the group consisting of benzenesulfonic acid, dodecylbenzenesulfonic acid, methanesulfonic acid, p-phenolsulfonic acid, p-toluenesulfonic acid and (poly)styrenesulfonic acid.
(有機ホスホン酸化合物)
有機ホスホン酸化合物は、分子構造中にリン酸基(-PO4H2)を1つ以上有する化合物であれば、特に限定されない。
例えば、1-ヒドロキシエチリデン-1,1-ジホスホン酸、1-ヒドロキシプロピリデン-1,1-ジホスホン酸、1-ヒドロキシブチリデン-1,1-ジホスホン酸、アミノトリメチレンホスホン酸、メチルジホスホン酸、ニトロトリスメチレンホスホン酸、エチレンジアミンテトラメチレンホスホン酸、エチレンジアミンビスメチレンホスホン酸、ヘキサメチレンジアミンテトラメチレンホスホン酸、ジエチレントリアミンペンタメチレンホスホン酸、シクロヘキサンジアミンテトラメチレンホスホン酸、カルボキシエチルホスホン酸、ホスホノ酢酸、2-ホスホノブタン-1,2,4-トリカルボン酸、2,3-ジカルボキシプロパン-1,1-ジホスホン酸、ホスホノブチル酸、ホスホノプロピオン酸、スルホニルメチルホスホン酸、N-カルボキシメチル-N,N-ジメチレンホスホン酸、N,N-ジカルボキシメチル-N-メチレンホスホン酸、2-エチルヘキシルアシッドホスフェート、ステアリルアシッドホスフェート、ベンゼンホスホン酸等からなる群より選ばれる1種以上が挙げられる。
(Organic phosphonic acid compound)
The organic phosphonic acid compound is not particularly limited as long as it is a compound having one or more phosphate groups (—PO 4 H 2 ) in its molecular structure.
For example, 1-hydroxyethylidene-1,1-diphosphonic acid, 1-hydroxypropylidene-1,1-diphosphonic acid, 1-hydroxybutylidene-1,1-diphosphonic acid, aminotrimethylenephosphonic acid, methyldiphosphonic acid , nitrotrismethylenephosphonic acid, ethylenediaminetetramethylenephosphonic acid, ethylenediaminebismethylenephosphonic acid, hexamethylenediaminetetramethylenephosphonic acid, diethylenetriaminepentamethylenephosphonic acid, cyclohexanediaminetetramethylenephosphonic acid, carboxyethylphosphonic acid, phosphonoacetic acid, 2- Phosphonobutane-1,2,4-tricarboxylic acid, 2,3-dicarboxypropane-1,1-diphosphonic acid, phosphonobutyric acid, phosphonopropionic acid, sulfonylmethylphosphonic acid, N-carboxymethyl-N,N-dimethylene phosphonic acid One or more selected from the group consisting of acids, N,N-dicarboxymethyl-N-methylenephosphonic acid, 2-ethylhexyl acid phosphate, stearyl acid phosphate, benzenephosphonic acid and the like.
有機ホスホン酸化合物は、分子構造中にリン酸基を有する界面活性剤であってもよい。
リン酸基を有する界面活性剤としては、分子構造中にポリオキシエチレン基又はフェニル基を有するものが好ましい。例えば、ポリオキシエチレンアルキルフェニルエーテルリン酸、ポリオキシエチレンアルキルエーテルリン酸、ジポリオキシプロピレンラウリルエーテルリン酸、ジポリオキシエチレンオレイルエーテルリン酸、ジポリオキシエチレンオキシプロピレンラウリルエーテルリン酸、ジポリオキシプロピレンオレイルエーテルリン酸、ラウリルリン酸アンモニウム、オクチルエ-テルリン酸アンモニウム、セチルエーテルリン酸アンモニウム、ポリオキシエチレンラウリルエーテルリン酸、ポリオキシエチレンオキシプロピレンラウリルエーテルリン酸、ポリオキシプロピレンラウリルエーテルリン酸、ポリオキシエチレントリスチリルフェニルエーテルリン酸、ポリオキシエチレンオキシプロピレントリスチリルフェニルエーテルリン酸、ポリオキシプロピレントリスチリルフェニルエーテルリン酸等からなる群より選ばれる1種以上が挙げられる。
リン酸基を有する界面活性剤としては、東邦化学工業社製の商品名フォスファノールやビックケミー・ジャパン社製のDisperbyk等の市販品からなる群より選ばれる1種以上を用いることができる。
The organic phosphonic acid compound may be a surfactant having a phosphate group in its molecular structure.
A surfactant having a phosphate group preferably has a polyoxyethylene group or a phenyl group in its molecular structure. For example, polyoxyethylene alkylphenyl ether phosphate, polyoxyethylene alkyl ether phosphate, dipolyoxypropylene lauryl ether phosphate, dipolyoxyethylene oleyl ether phosphate, dipolyoxyethyleneoxypropylene lauryl ether phosphate, dipoly Oxypropylene oleyl ether phosphate, ammonium lauryl phosphate, octyl ether ammonium terphosphate, cetyl ether ammonium phosphate, polyoxyethylene lauryl ether phosphate, polyoxyethylene oxypropylene lauryl ether phosphate, polyoxypropylene lauryl ether phosphate, One or more selected from the group consisting of polyoxyethylene tristyrylphenyl ether phosphate, polyoxyethyleneoxypropylene tristyrylphenyl ether phosphate, polyoxypropylene tristyrylphenyl ether phosphate and the like.
As the surfactant having a phosphate group, one or more selected from the group consisting of commercially available products such as Phosphanol (trade name, manufactured by Toho Chemical Industry Co., Ltd.) and Disperbyk (manufactured by BYK-Chemie Japan) can be used.
(含有量)
導電性樹脂組成物における、(c)有機酸化合物の含有量は、特に限定されない。(a)錫粉末、(b)エポキシ樹脂、(c)有機酸化合物及び(d)チオール系硬化剤の合計量を100質量%として、例えば0.1質量%以上、好ましくは0.3質量%以上、より好ましくは0.5質量%以上であり、例えば9.4質量%以下、好ましくは8.0質量%以下、より好ましくは7.0質量%以下である。
(a)錫粉末、(b)エポキシ樹脂、(c)有機酸化合物及び(d)チオール系硬化剤の合計量100質量%における(c)有機酸化合物の含有量が0.1質量%未満であると、膜形成ができない、塗膜の接合強度が低下する、硬化に時間がかかる等のおそれがあり、含有量が9.4質量%を超えると、導電性が低下し、体積抵抗率が上昇する又は実施例に記載するLED点灯試験でLEDが点灯しない、膜形成ができなくなる等のおそれがある。
(Content)
The content of (c) the organic acid compound in the conductive resin composition is not particularly limited. When the total amount of (a) tin powder, (b) epoxy resin, (c) organic acid compound and (d) thiol-based curing agent is 100% by mass, for example, 0.1% by mass or more, preferably 0.3% by mass Above, more preferably 0.5% by mass or more, for example, 9.4% by mass or less, preferably 8.0% by mass or less, more preferably 7.0% by mass or less.
(a) tin powder, (b) epoxy resin, (c) organic acid compound and (d) thiol-based curing agent, the content of (c) organic acid compound is less than 0.1% by mass based on the total amount of 100% by mass. If there is, there is a risk that film formation will not be possible, the bonding strength of the coating film will decrease, and curing will take a long time. There is a risk that the LED will not light in the LED lighting test described in the Examples, or that film formation will not be possible.
<(d)チオール系硬化剤>
チオール系硬化剤としては、分子構造中にエポキシ基と反応し得るチオール基を1つ以上、好ましくは2つ以上有するチオール化合物が挙げられる。チオール系硬化剤として、分子構造中のチオール基数が2~6(2官能~6官能)である多官能チオール化合物が好ましく、3~6(3官能~6官能)である多官能チオール化合物がより好ましい。チオール当量は、特に限定されないが、例えば低分子のチオール系硬化剤では50g/eq以上、好ましくは70g/eq以上であり、例えば200g/eq以下、好ましくは150g/eq以下である。高分子のチオール系硬化剤では250g/eq以上、好ましくは400g/eq以上であり、例えば5000g/eq以下、好ましくは3000g/eq以下である。
<(d) Thiol-based curing agent>
The thiol-based curing agent includes a thiol compound having one or more, preferably two or more thiol groups capable of reacting with an epoxy group in its molecular structure. As a thiol-based curing agent, a polyfunctional thiol compound having 2 to 6 (difunctional to hexafunctional) thiol groups in the molecular structure is preferred, and a polyfunctional thiol compound having 3 to 6 (trifunctional to hexafunctional) is more preferred. preferable. Although the thiol equivalent is not particularly limited, for example, in the case of a low molecular weight thiol-based curing agent, it is 50 g/eq or more, preferably 70 g/eq or more, and for example 200 g/eq or less, preferably 150 g/eq or less. A polymer thiol-based curing agent is 250 g/eq or more, preferably 400 g/eq or more, and for example, 5000 g/eq or less, preferably 3000 g/eq or less.
チオール系硬化剤としては、例えば、トリメチロールプロパントリス(3-メルカプトプロピオネート)(略称:TMTP)、ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)(略称:PEMP)、ジペンタエリスリトールヘキサキス(3-メルカプトプロピオネート)(略称:DPMP)、トリス-[(3-メルカプトプロピオニルオキシ)-エチル]-イソシアヌレート(略称:TEMPIC)、トリス(3-メルカプトプロピル)イソシアヌレート(略称:TMPIC)、エチレングリコールビスチオグリコレート(略称:EGTG)、トリメチロールプロパントリスチオグリコレート(略称:TMTG)、ペンタエリスリトールテトラキスチオグリコレート(略称:PETG)、ペンタエリスリトールテトラキス(3-メルカプトブチレート)、1,4-ビス(3-メルカプトブチリルオキシ)ブタン、1,3,5-トリス(3-メルカプトブチリルオキシエチル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、トリメチロールプロパントリス(3-メルカプトブチレート)(略称:TPMB)、トリメチロールエタントリス(3-メルカプトブチレート)(略称:TEMB)、1,3,4,6-テトラキス(2-メルカプトエチル)グリコールウリル、1,3,4,6-テトラキス(2-メルカプトプロピル)グリコールウリル、4,4’-イソプロピリデンビス[(3-メルカプトプロポキシ)ベンゼン]、1,3,5-トリアジンー2,4,6-トリチオール等のチオール化合物(多官能チオール化合物)、チオール基を有するポリサルファイドポリマ等が挙げられる。これらは、1種類を単独で用いてもよく、2種以上組み合わせて用いてもよい。 Thiol-based curing agents include, for example, trimethylolpropane tris (3-mercaptopropionate) (abbreviation: TMTP), pentaerythritol tetrakis (3-mercaptopropionate) (abbreviation: PEMP), dipentaerythritol hexakis ( 3-mercaptopropionate) (abbreviation: DPMP), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate (abbreviation: TEMPIC), tris(3-mercaptopropyl) isocyanurate (abbreviation: TMPIC), ethylene glycol bisthioglycolate (abbreviation: EGTG), trimethylolpropane tristhioglycolate (abbreviation: TMTG), pentaerythritol tetrakisthioglycolate (abbreviation: PETG), pentaerythritol tetrakis(3-mercaptobutyrate), 1, 4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H) -trione, trimethylolpropane tris (3-mercaptobutyrate) (abbreviation: TPMB), trimethylolethane tris (3-mercaptobutyrate) (abbreviation: TEMB), 1,3,4,6-tetrakis (2-mercapto ethyl)glycoluril, 1,3,4,6-tetrakis(2-mercaptopropyl)glycoluril, 4,4'-isopropylidenebis[(3-mercaptopropoxy)benzene], 1,3,5-triazine-2, Thiol compounds (polyfunctional thiol compounds) such as 4,6-trithiol, polysulfide polymers having thiol groups, and the like can be mentioned. These may be used individually by 1 type, and may be used in combination of 2 or more types.
具体的には、例えば、SC有機化学社製多官能チオール(TMMP-LV、PEMP-LV、DPMP、TEMPIC、PEMP等)、東レファインケミカル社製多官能チオール(QE-340M、LP-2、LP-3、LP-55、LP-31等)、四国化成工業社製多官能チオール(TS-G、C3TS-G等)、昭和電工社製多官能チオール(カレンズ MTシリーズ(PE-1、BD-1、NR-1、TPMB、TEMB等))、淀化学社製多官能チオール(OTG、EGTG、TMTG、PETG、3-MPA、TMTP、PETP等)等が挙げられる。 Specifically, for example, polyfunctional thiol manufactured by SC Organic Chemical Co., Ltd. (TMMP-LV, PEMP-LV, DPMP, TEMPIC, PEMP, etc.), polyfunctional thiol manufactured by Toray Fine Chemicals Co., Ltd. (QE-340M, LP-2, LP- 3, LP-55, LP-31, etc.), polyfunctional thiol manufactured by Shikoku Kasei Kogyo Co., Ltd. (TS-G, C3TS-G, etc.), polyfunctional thiol manufactured by Showa Denko Co., Ltd. (Karenzu MT series (PE-1, BD-1 , NR-1, TPMB, TEMB, etc.), polyfunctional thiols manufactured by Yodo Chemical Co., Ltd. (OTG, EGTG, TMTG, PETG, 3-MPA, TMTP, PETP, etc.).
導電性樹脂組成物における、(d)チオール系硬化剤の含有量は、特に限定されない。エポキシ樹脂のエポキシ基1当量に対して、チオール基が、例えば0.05当量以上、好ましくは0.2当量以上であり、例えば1.5当量以下、好ましくは1.2当量以下、より好ましくは1.1当量以下、さらに好ましくは1.0当量以下である。エポキシ基1当量に対して0.1当量未満の場合、導電性樹脂組成物の硬化性が低下し、硬化に時間がかかる又は塗膜の硬化不良が発生するおそれがあり、1.5当量を超える場合、過剰となる硬化剤未反応物の影響で塗膜の硬化不良が発生し、塗膜硬度が低下するおそれがあり、導電接続の信頼性が低下するおそれがある。
また、導電性樹脂組成物における、(d)チオール系硬化剤の含有量は、エポキシ樹脂100質量部に対して、例えば5質量部以上、好ましくは10質量部以上、より好ましくは15質量部以上であり、例えば250質量部以下、好ましくは200質量部以下、より好ましくは180質量部以下とすることができる。エポキシ樹脂100質量部に対して硬化剤の含有量が5質量部未満の場合、導電性樹脂組成物の硬化性が低下し、硬化に時間がかかるおそれがあり、250質量部を超える場合、導電性樹脂組成物が固化せず膜形成しないおそれがある。
The content of (d) the thiol-based curing agent in the conductive resin composition is not particularly limited. The thiol group is, for example, 0.05 equivalent or more, preferably 0.2 equivalent or more, for example 1.5 equivalent or less, preferably 1.2 equivalent or less, more preferably 1 equivalent of the epoxy group of the epoxy resin. It is 1.1 equivalents or less, more preferably 1.0 equivalents or less. If the amount is less than 0.1 equivalent with respect to 1 equivalent of the epoxy group, the curability of the conductive resin composition may decrease, and the curing may take a long time or the coating film may be poorly cured. If it exceeds, the excessive unreacted product of the curing agent may cause poor curing of the coating film, which may reduce the hardness of the coating film and reduce the reliability of the conductive connection.
In addition, the content of (d) the thiol-based curing agent in the conductive resin composition is, for example, 5 parts by mass or more, preferably 10 parts by mass or more, more preferably 15 parts by mass or more with respect to 100 parts by mass of the epoxy resin. and, for example, 250 parts by mass or less, preferably 200 parts by mass or less, and more preferably 180 parts by mass or less. If the content of the curing agent is less than 5 parts by mass with respect to 100 parts by mass of the epoxy resin, the curability of the conductive resin composition may decrease, and curing may take a long time. There is a risk that the flexible resin composition will not solidify and form a film.
<その他成分>
本発明の導電性樹脂組成物は、必要に応じて、溶媒、チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤、密着性付与剤、粘弾性調整剤、湿潤分散剤、硬化促進剤(硬化触媒)、反応性希釈剤、錫粉末以外の導電性粉末、エポキシ樹脂以外の樹脂、酸化防止剤、顔料、充填剤(フィラー)、腐食抑制剤、消泡剤、カップリング剤、沈降防止剤等、レベリング剤、重金属不活性化剤、界面活性剤、pH調整剤、紫外線吸収剤、難燃剤、接着付与剤等からなる群より選ばれる1種以上の各種添加剤を混合することができる。
<Other ingredients>
The conductive resin composition of the present invention may optionally contain a solvent, a curing agent for curing an epoxy resin other than a thiol-based curing agent, an adhesion imparting agent, a viscoelasticity modifier, a wetting and dispersing agent, a curing accelerator (curing catalysts), reactive diluents, conductive powders other than tin powders, resins other than epoxy resins, antioxidants, pigments, fillers, corrosion inhibitors, antifoaming agents, coupling agents, anti-settling agents, etc. , a leveling agent, a heavy metal deactivator, a surfactant, a pH adjuster, an ultraviolet absorber, a flame retardant, an adhesion imparting agent, and the like.
(溶媒)
本発明の導電性樹脂組成物は、溶媒を含んでいてもよい。これにより、導電性樹脂組成物の流動性を向上させ、作業性の向上に寄与することができる。また、導電性樹脂組成物と溶媒を混合することで、導電性樹脂ペースト、導電性インク、導電性接着剤、回路接続材料等を構成することができる。
(solvent)
The conductive resin composition of the present invention may contain a solvent. This can improve the fluidity of the conductive resin composition and contribute to the improvement of workability. Further, by mixing the conductive resin composition and the solvent, conductive resin paste, conductive ink, conductive adhesive, circuit connecting material, etc. can be formed.
溶媒としては、水及び各種有機溶媒からなる群より選ばれる1種以上から、任意のものを用いることができる。有機溶媒としては、例えば、エチルアルコール、プロピルアルコール、ブチルアルコール、ペンチルアルコール、ヘキシルアルコール、ヘプチルアルコール、オクチルアルコール、ノニルアルコール、デシルアルコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、エチルカルビトール、ブチルカルビトール、2-エチル-1、3-ヘキサンジオール、メチルメトキシブタノール、α-ターピネオール、β-ターピネオール、へキシレングリコール、ベンジルアルコール、2-フェニルエチルアルコール、イゾパルミチルアルコール、イソステアリルアルコール、ラウリルアルコール、エチレングリコール、プロピレングリコールもしくはグリセリン等のアルコール類;アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、ジアセトンアルコール(4-ヒドロキシ-4-メチル-2-ペンタノン)、2-オクタノン、イソホロン(3,5,5-トリメチル-2-シクロヘキセン-1-オン)もしくはジイソブチルケトン(2,6-ジメチル-4-ヘプタノン)等のケトン系溶媒;酢酸エチル、酢酸ブチル、ジエチルフタレート、ジブチルフタレート、アセトキシエタン、酪酸メチル、ヘキサン酸メチル、オクタン酸メチル、デカン酸メチル、メチルセロソルブアセテート、エチレングリコールモノブチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、エチルジグリコールアセテート、1,2-ジアセトキシエタン等のエステル系溶媒;テトラヒドロフラン、ジメチルエーテル、ジエチルエーテル、ジプロピルエーテル、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールジブチルエーテル、プロピレングリコールジメチルエーテル、エトキシエチルエーテル、1,2-ビス(2-ジエトキシ)エタンもしくは1,2-ビス(2-メトキシエトキシ)エタン等のエーテル系溶媒;酢酸2-(2-ブトキシエトキシ)エタン等のエステルエーテル類;2-(2-メトキシエトキシ)エタノール等のエーテルアルコール系溶媒;ベンゼン、トルエン、キシレン、n-パラフィン、イソパラフィン、ドデシルベンゼン、テレピン油、ケロシンもしくは軽油等の炭化水素系溶媒;アセトニトリル、プロピオニトリル等のニトリル系溶媒;ジメチルアセトアミド、N,N-ジメチルホルムアミド、N-メチル-2-ピロリドン等の含窒素極性溶媒;シリコーンオイル系溶媒等からなる群より選ばれる1種以上が挙げられる。
溶剤を用いる場合の含有量は、特に限定されず、導電性樹脂組成物の粘度が、基材上に適切に塗布、印刷等できる程度の粘度及び/又は多孔質体に適切に含浸し得る程度の粘度となるように適宜調整すればよい。
Any one or more selected from the group consisting of water and various organic solvents can be used as the solvent. Examples of organic solvents include ethyl alcohol, propyl alcohol, butyl alcohol, pentyl alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and ethylene glycol monopropyl ether. , ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, ethyl carbitol, butyl carbitol, 2-ethyl-1,3- Alcohols such as hexanediol, methylmethoxybutanol, α-terpineol, β-terpineol, hexylene glycol, benzyl alcohol, 2-phenylethyl alcohol, isopalmityl alcohol, isostearyl alcohol, lauryl alcohol, ethylene glycol, propylene glycol or glycerin Classes; acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol (4-hydroxy-4-methyl-2-pentanone), 2-octanone, isophorone (3,5,5-trimethyl-2-cyclohexene-1-one ) or ketone solvents such as diisobutyl ketone (2,6-dimethyl-4-heptanone); ethyl acetate, butyl acetate, diethyl phthalate, dibutyl phthalate, acetoxyethane, methyl butyrate, methyl hexanoate, methyl octanoate, methyl decanoate , methyl cellosolve acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, ethyl diglycol acetate, ester solvents such as 1,2-diacetoxyethane; tetrahydrofuran, dimethyl ether, diethyl ether, dipropyl ether, ethylene glycol dimethyl ether, Ether solvents such as ethylene glycol diethyl ether, ethylene glycol dibutyl ether, propylene glycol dimethyl ether, ethoxyethyl ether, 1,2-bis(2-diethoxy)ethane or 1,2-bis(2-methoxyethoxy)ethane; acetic acid 2 -Ester ethers such as (2-butoxyethoxy)ethane; ether alcohol solvents such as 2-(2-methoxyethoxy)ethanol; benzene, toluene, xylene, n-paraffin, isoparaffin, dodecylbenzene, turpentine oil, kerosene or Hydrocarbon solvents such as light oil; Nitrile solvents such as acetonitrile and propionitrile; Nitrogen-containing polar solvents such as dimethylacetamide, N,N-dimethylformamide and N-methyl-2-pyrrolidone; Silicone oil solvents, etc. One or more selected from the group can be mentioned.
When using a solvent, the content is not particularly limited, and the viscosity of the conductive resin composition is such that it can be appropriately applied, printed, etc. on the substrate and / or can be appropriately impregnated into the porous body. The viscosity may be adjusted as appropriate.
(チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤)
本発明の導電性樹脂組成物は、チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤を含んでいてもよい。チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤としては、例えば、酸無水物系硬化剤、フェノール系硬化剤、アミン系硬化剤及びアミド系硬化剤等が挙げられる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。本発明の導電性樹脂組成物は、作業性や取扱性等をより効果的に向上させる観点から、25℃において液状である硬化剤を含むことが好ましい。
(Curing agent for curing epoxy resin other than thiol-based curing agent)
The conductive resin composition of the present invention may contain a curing agent that cures the epoxy resin other than the thiol-based curing agent. Examples of curing agents for curing epoxy resins other than thiol-based curing agents include acid anhydride-based curing agents, phenol-based curing agents, amine-based curing agents, and amide-based curing agents. These may be used individually by 1 type, and may be used in combination of 2 or more types. The conductive resin composition of the present invention preferably contains a curing agent that is liquid at 25° C. from the viewpoint of more effectively improving workability, handleability, and the like.
-酸無水物系硬化剤-
酸無水物系硬化剤は、分子構造中にカルボン酸無水物基(-C(=O)-O-C(=O)-)を1つ以上有する化合物であれば、特に限定されない。
酸無水物系硬化剤は、有機カルボン酸2分子の分子間での脱水及び/又は有機カルボン酸1分子の分子構造中での脱水により得られたものである。本発明においては、例えば、前記有機カルボン酸のうち、有機モノカルボン酸の分子間脱水により得られたもの及び有機ポリカルボン酸の分子内脱水及び/又は分子間脱水により得られるものからなる群より選ばれる1種以上が挙げられる。例えば、脂肪族モノカルボン酸無水物、脂肪族ポリカルボン酸無水物、脂環族ポリカルボン酸無水物、芳香族ポリカルボン酸無水物等からなる群より選ばれる1種以上が挙げられる。
- Acid anhydride curing agent -
The acid anhydride-based curing agent is not particularly limited as long as it is a compound having one or more carboxylic acid anhydride groups (-C(=O)-OC(=O)-) in its molecular structure.
The acid anhydride-based curing agent is obtained by dehydration between two organic carboxylic acid molecules and/or dehydration within the molecular structure of one organic carboxylic acid molecule. In the present invention, for example, among the organic carboxylic acids, from the group consisting of those obtained by intermolecular dehydration of organic monocarboxylic acids and those obtained by intramolecular dehydration and/or intermolecular dehydration of organic polycarboxylic acids One or more selected types can be mentioned. Examples thereof include one or more selected from the group consisting of aliphatic monocarboxylic anhydrides, aliphatic polycarboxylic anhydrides, alicyclic polycarboxylic anhydrides, aromatic polycarboxylic anhydrides, and the like.
好ましくは、酢酸無水物、プロピオン酸無水物、シュウ酸無水物、マレイン酸無水物、フタル酸無水物、安息香酸無水物、コハク酸無水物、2-メチルコハク酸無水物、トリメリット酸無水物、ピロメリット酸無水物、テトラヒドロフタル酸無水物、メチルテトラヒドロフタル酸無水物、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、(ポリ)アジピン酸無水物、(ポリ)アゼライン酸無水物、(ポリ)セバシン酸無水物、ノルボルネン-2,3-ジカルボン酸無水物、メチル-5-ノルボルネン-2,3-ジカルボン酸無水物等からなる群より選ばれる1種以上が挙げられる。 Preferably, acetic anhydride, propionic anhydride, oxalic anhydride, maleic anhydride, phthalic anhydride, benzoic anhydride, succinic anhydride, 2-methylsuccinic anhydride, trimellitic anhydride, pyromellitic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, (poly)adipic anhydride, (poly)azelaic anhydride, One or more selected from the group consisting of (poly)sebacic anhydride, norbornene-2,3-dicarboxylic anhydride, methyl-5-norbornene-2,3-dicarboxylic anhydride and the like.
また、下記構造式(1)
で表されるポリ酸ポリ無水物を用いてもよい。このようなポリ酸ポリ無水物は、長鎖脂肪族ジカルボン酸が分子間脱水縮合反応することで得られるものである。
ポリ酸ポリ無水物としては、例えば、岡村製油社製のSL-12AH、SL-20AH、SB-20AH、IPU-22AH、ST-2PAH等の1種以上が挙げられる。特に、25℃で液状のSB-20AH、IPU-22AH及びST-2PAHの1種以上が好ましい。
In addition, the following structural formula (1)
A polyacid polyanhydride represented by may be used. Such a polyacid polyanhydride is obtained by an intermolecular dehydration condensation reaction of a long-chain aliphatic dicarboxylic acid.
Examples of the polyacid polyanhydride include one or more of SL-12AH, SL-20AH, SB-20AH, IPU-22AH, ST-2PAH manufactured by Okamura Oil Co., Ltd., and the like. In particular, one or more of SB-20AH, IPU-22AH and ST-2PAH, which are liquid at 25°C, are preferred.
-フェノール系硬化剤-
フェノール系硬化剤としては、分子構造中にエポキシ基と反応し得るフェノール性水酸基を1つ以上、好ましくは2つ以上有する化合物が挙げられる。例えば、ビスフェノールA、ビスフェノールB、ビスフェノールF、ビスフェノールAD、ビスフェノールS等のビスフェノール類;ビフェノール、テトラメチルビフェノール等のビフェノール類;ヒドロキシフェノール、ビス(4-ヒドロキシフェニル)エーテル等のフェノール類;アルキルフェノール類;2,6-ビス[(2-ヒドロキシフェニル)メチル]-フェノール、フェノールビフェニレンノボラック(ビフェニルアラルキルフェノール)等のフェノールノボラック類;o-クレゾールノボラック、m-クレゾールノボラック、p-クレゾールノボラック等のクレゾールノボラック類;トリフェニルメタン類;テトラキスフェノール類;フェノール樹脂類;フェノールノボラック樹脂;ビフェニルアラルキル型フェノール樹脂;等が例示できる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。
具体的には、4,4’,4’’-トリヒドロキシトリフェニルメタン、4,4’,4’’,4’’’-メタンテトライルテトラフェノール、1、1、2、2-テトラキス(4-ヒドロキシフェニル)エタン、明和化成社製のMEH-8005、日本化薬社製のKAYAHARD GPH-65、KAYAHARD GPH-103、アイカ工業社製のBRG-555、BRG-556、BRG-557、BRG-558、CRG-951、TAM-005等が挙げられる。
- Phenolic curing agent -
Examples of phenol-based curing agents include compounds having one or more, preferably two or more phenolic hydroxyl groups capable of reacting with epoxy groups in their molecular structure. For example, bisphenols such as bisphenol A, bisphenol B, bisphenol F, bisphenol AD, and bisphenol S; biphenols such as biphenol and tetramethylbiphenol; phenols such as hydroxyphenol and bis(4-hydroxyphenyl) ether; alkylphenols; Phenol novolaks such as 2,6-bis[(2-hydroxyphenyl)methyl]-phenol, phenolbiphenylene novolak (biphenylaralkylphenol); Cresol novolaks such as o-cresol novolak, m-cresol novolak and p-cresol novolak ; triphenylmethanes; tetrakisphenols; phenol resins; phenol novolak resins; biphenylaralkyl type phenol resins; These may be used individually by 1 type, and may be used in combination of 2 or more types.
Specifically, 4,4′,4″-trihydroxytriphenylmethane, 4,4′,4″,4′″-methanetetrayltetraphenol, 1,1,2,2-tetrakis ( 4-hydroxyphenyl) ethane, MEH-8005 manufactured by Meiwa Kasei Co., Ltd., KAYAHARD GPH-65 manufactured by Nippon Kayaku Co., Ltd., KAYAHARD GPH-103, BRG-555 manufactured by Aica Kogyo Co., Ltd., BRG-556, BRG-557, BRG -558, CRG-951, TAM-005 and the like.
本発明においては、例えばフェノール樹脂が好ましく用いられる。このようなフェノール樹脂としては、水酸基当量が、例えば50g/eq以上、好ましくは100g/eq以上であり、より好ましくは300g/eq以下である。 In the present invention, for example, phenol resin is preferably used. Such a phenol resin has a hydroxyl equivalent of, for example, 50 g/eq or more, preferably 100 g/eq or more, and more preferably 300 g/eq or less.
-アミン系硬化剤-
アミン系硬化剤としては、例えば、ジエチレントリアミン、トリエチレンテトラミン、ジエチルアミノプロピルアミン、メンタンジアミン、イソホロンジアミン、ビス[4-アミノ-3-メチルジシクロヘキシル]メタン、ジアミノジシクロヘキシルメタン、ビス(アミノメチル)シクロヘキサン、m-キシリレンジアミン、メタフェニレンジアミン、ジアミノジフェニルメタン、ジアミノジエチルジフェニルメタン及びこれらをエポキシアダクト、マイケル付加、マンニッヒ反応等により変性した変性ポリアミン、ポリアミドアミン等が挙げられる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。
- Amine curing agent -
Amine curing agents include, for example, diethylenetriamine, triethylenetetramine, diethylaminopropylamine, menthanediamine, isophoronediamine, bis[4-amino-3-methyldicyclohexyl]methane, diaminodicyclohexylmethane, bis(aminomethyl)cyclohexane, m -xylylenediamine, metaphenylenediamine, diaminodiphenylmethane, diaminodiethyldiphenylmethane, and modified polyamines and polyamidoamines obtained by modifying these by epoxy adduct, Michael addition, Mannich reaction, and the like. These may be used individually by 1 type, and may be used in combination of 2 or more types.
-チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤の含有量-
導電性樹脂組成物における、チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤の含有量は、特に限定されない。本発明においては、チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤を使用しなくてもよい。
チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤を含有する場合、エポキシ樹脂のエポキシ基1当量に対して、硬化剤中のエポキシ基と反応する基(例えば、ヒドロキシ基、アミノ基、酸無水物基等)が、例えば0.1当量以上、好ましくは0.3当量以上、より好ましくは0.9当量以上であり、例えば1.5当量以下、好ましくは1.2当量以下、より好ましくは1.1当量以下である。最も好ましくは1.0当量である。エポキシ基1当量に対して0.1当量未満の場合、導電性樹脂組成物の硬化性が低下し、硬化に時間がかかる又は塗膜の硬化不良が発生するおそれがあり、1.5当量を超える場合、過剰となる硬化剤未反応物の影響で塗膜の硬化不良が発生し、塗膜硬度が低下するおそれがあり、導電接続の信頼性が低下するおそれがある。
また、エポキシ樹脂100質量部に対して、硬化剤全体が、例えば5質量部以上、好ましくは10質量部以上、より好ましくは15質量部以上であり、例えば250質量部以下、好ましくは200質量部以下、より好ましくは180質量部以下となるようにできる。エポキシ樹脂100質量部に対して硬化剤の含有量が5質量部未満の場合、導電性樹脂組成物の硬化性が低下し、硬化に時間がかかるおそれがあり、250質量部を超える場合、導電性樹脂組成物が固体とならなくなるおそれがある。
- Content of curing agent for curing epoxy resin other than thiol-based curing agent -
The content of the curing agent for curing the epoxy resin other than the thiol-based curing agent in the conductive resin composition is not particularly limited. In the present invention, it is not necessary to use a curing agent for curing the epoxy resin other than the thiol-based curing agent.
When a curing agent other than a thiol-based curing agent that cures an epoxy resin is contained, a group that reacts with an epoxy group in the curing agent (e.g., a hydroxy group, an amino group, an acid anhydride group, etc.) is, for example, 0.1 equivalent or more, preferably 0.3 equivalent or more, more preferably 0.9 equivalent or more, for example 1.5 equivalent or less, preferably 1.2 equivalent or less, more preferably 1.1 equivalents or less. Most preferably it is 1.0 equivalent. If the amount is less than 0.1 equivalent with respect to 1 equivalent of the epoxy group, the curability of the conductive resin composition may be lowered, and the curing may take a long time or the coating film may be poorly cured. If it exceeds, the excessive unreacted product of the curing agent may cause poor curing of the coating film, which may reduce the hardness of the coating film and reduce the reliability of the conductive connection.
Further, the total curing agent is, for example, 5 parts by mass or more, preferably 10 parts by mass or more, more preferably 15 parts by mass or more, for example 250 parts by mass or less, preferably 200 parts by mass, relative to 100 parts by mass of the epoxy resin. Below, more preferably 180 parts by mass or less. If the content of the curing agent is less than 5 parts by mass with respect to 100 parts by mass of the epoxy resin, the curability of the conductive resin composition may decrease, and curing may take a long time. There is a risk that the flexible resin composition will not become solid.
(密着性付与剤)
本発明の導電性樹脂組成物は、密着性付与剤を含んでいてもよい。これにより、導電性樹脂組成物を基材に塗布した際に、基材との密着性等を向上させることができる。密着性付与剤としては、例えば、トリアゾール化合物、チアゾール化合物、トリアジン化合物、官能基(カルボン酸基、アミノ基、水酸基等)を有するポリマーやその塩等が挙げられる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。
密着性付与剤としては、例えば、ビックケミー・ジャパン社製BYKシリーズ(4509、4510、4512等)が挙げられる。
(Adhesion imparting agent)
The conductive resin composition of the present invention may contain an adhesion imparting agent. As a result, when the conductive resin composition is applied to the substrate, the adhesion to the substrate can be improved. Examples of adhesion-imparting agents include triazole compounds, thiazole compounds, triazine compounds, polymers having functional groups (carboxylic acid groups, amino groups, hydroxyl groups, etc.) and salts thereof. These may be used individually by 1 type, and may be used in combination of 2 or more types.
Examples of adhesion-imparting agents include BYK series (4509, 4510, 4512, etc.) manufactured by BYK-Chemie Japan.
(粘弾性調整剤)
本発明の導電性樹脂組成物は、粘弾性調整剤(レオロジーコントロール剤)を含んでいてもよい。これにより、導電性樹脂組成物の粘弾性(レオロジー)を調製して、作業性等の向上に寄与することができる。
粘弾性調整剤(レオロジーコントロール剤)としては、ポリアマイド系、アミノプラスト系、ポリカルボン酸系、ウレタン系、セルロース系、無機層状化合物系等の粘弾性調整剤(レオロジーコントロール剤)が挙げられる。例えば、ビックケミー・ジャパン社製RHEOBYKシリーズ(H370、H400、H600、H600VF、100、405、410、411、415、430、431、440、7410ET等);楠本化成社製ディスパロンシリーズ(AQ-600、AQH-800、3600N、3900EF等);サンノプコ社製SNシックナーシリーズ(613、617、618、630、634、636、621N、623N等);ADEKA社製アデカノールシリーズ(UH-814N、UH-752、UH-750、UH-462等)、ダイセル社製HECダイセルシリーズ(SP600N等);エレメンティスジャパン社製BENTONE HD等が挙げられる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。
(viscoelasticity modifier)
The conductive resin composition of the present invention may contain a viscoelasticity modifier (rheology control agent). This makes it possible to adjust the viscoelasticity (rheology) of the conductive resin composition and contribute to improvement in workability and the like.
Viscoelasticity modifiers (rheology control agents) include polyamide-based, aminoplast-based, polycarboxylic acid-based, urethane-based, cellulose-based, inorganic layered compound-based viscoelasticity-adjusting agents (rheology control agents). For example, BYK-Chemie Japan RHEOBYK series (H370, H400, H600, H600VF, 100, 405, 410, 411, 415, 430, 431, 440, 7410ET, etc.); AQH-800, 3600N, 3900EF, etc.); San Nopco SN Thickener series (613, 617, 618, 630, 634, 636, 621N, 623N, etc.); ADEKA Adekanol series (UH-814N, UH-752, UH-750, UH-462, etc.), HEC Daicel series (SP600N, etc.) manufactured by Daicel; BENTONE HD manufactured by Elementis Japan; These may be used individually by 1 type, and may be used in combination of 2 or more types.
(湿潤分散剤)
本発明の導電性樹脂組成物は、錫粉末の凝集を防止するために、必要に応じて湿潤分散剤を含有していてもよい。
湿潤分散剤の具体例としては、例えば、日本ルーブリゾール社製ソルスパースシリーズ(9000、12000、17000、20000、21000、24000、26000、27000、28000、32000、35100、54000等)、エフカアディディブズ社製EFKAシリーズ(4008、4009、4010、4015、4046、4047、4060、4080、7462、4020、4050、4055、4400、4401、4402、4403、4300、4330、4340、6220、6225、6700、6780、6782、8503等)、味の素ファインテクノ社製アジスパーシリーズ(PA111、PB711、PB821、PB822、PN411等)、ビックケミー・ジャパン社製DISPERBYKシリーズ(101、106、108、116、130、140、145、161、163、166、168、171、180、192、2000、2001、2020、2025、2070、2152、2155、2164、220S、300、320、340、378、380N、410、425、430等)等が挙げられる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。
(Wetting and dispersing agent)
The conductive resin composition of the present invention may optionally contain a wetting and dispersing agent to prevent aggregation of the tin powder.
Specific examples of wetting and dispersing agents include Solsperse series manufactured by Nippon Lubrizol (9000, 12000, 17000, 20000, 21000, 24000, 26000, 27000, 28000, 32000, 35100, 54000, etc.), Efca Additives Company EFKA series (4008, 4010, 4015, 4046, 4047, 4060, 4060, 4020, 4050, 4401, 4402, 4402, 4402, 4330, 4330, 4330, 6700, 6700, 6700, 6700, 6700, 6700, 6700, 6700, 6700, 6700, 6700, 6700, 6700, 6700, 6700. 780 , 6782, 8503, etc.), Ajinomoto Fine Techno Ajisper series (PA111, PB711, PB821, PB822, PN411, etc.), BYK Chemie Japan Co., Ltd. DISPERBYK series (101, 106, 108, 116, 130, 140, 145, 161, 163, 166, 168, 171, 180, 192, 2000, 2001, 2020, 2025, 2070, 2152, 2155, 2164, 220S, 300, 320, 340, 378, 380N, 410, 425, 430, etc.) is mentioned. These may be used individually by 1 type, and may be used in combination of 2 or more types.
(硬化促進剤(硬化触媒))
本発明の硬化性樹脂組成物は、エポキシ樹脂と硬化剤の硬化を促進させるための硬化促進剤(硬化触媒)を含有していてもよい。硬化促進剤としては、特に限定されないが、アミン系硬化促進剤、グアニジン系硬化促進剤、イミダゾール系硬化促進剤、ホスホニウム系硬化促進剤等が挙げられる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。例えば、トリエチルアミン、トリプロピルアミン、トリブチルアミン、ジメチルブチルアミン、ジメチルペンチルアミン、ジメチルシクロヘキシルアミン等の脂肪族第三アミン類、ジメチルベンジルアミン、ジメチルアミノメチルフェノール、ジメチルアミノ-p-クレゾール、ピペリジン、α-ピコリン、ピリジン、4-ジメチルアミノピリジン、2,4,6-トリス(ジメチルアミノメチル)フェノール、3,4,5-トリス(ジメチルアミノメチル)フェノール、2-メチルイミダゾール、2-エチル-4-メチルイミダゾール、2-ウンデシルイミダゾール、2-フェニルイミダゾール、1-ベンジル-2-メチルイミダゾール、1-シアノエチル-2-メチルイミダゾール、1-シアノエチル-2-エチル-4-メチルイミダゾール、N-アミノエチルピペラジン、1,3,6-トリスアミノメチルヘキサン、m-キシレンジアミン、p-キシレンジアミン、N-(2-アミノエチル)ピペラジン、m-フェニレンジアミン、p-フェニレンジアミン、ジアミノジフェニルメタン、メチレンジアニリン、2,4-トルエンジアミン、2,4-ジアミノアニゾール、2,4-トルエンジアミン、2,4-ジアミノジフェニルアミン、4,4’-メチレンジアニリン、1,3-ジアミノシクロヘキサン、3,9-ビス(3-アミノプロピル)-2,4,8,10-テトラピロ[5,5]ウンデカン、1,8-ジアザビシクロ[5,4,0]ウンデセン-7、1,5-ジアザビシクロ(4,3,0)-ノネン、ポリアミン、ポリアミドアミン、ポリアミド、変性ポリアミン、変性ポリアミドアミン、変性ポリアミド等のアミン系化合物;ジシアンジアミド、1-メチルグアニジン、1-エチルグアニジン、1-シクロヘキシルグアニジン、1-フェニルグアニジン、1-(o-トリル)グアニジン、ジメチルグアニジン、ジフェニルグアニジン、ジ(o-トリル)グアニジン、トリメチルグアニジン、テトラメチルグアニジン、ペンタメチルグアニジン、1,5,7-トリアザビシクロ[4.4.0]デカ-5-エン、7-メチル-1,5,7-トリアザビシクロ[4.4.0]デカ-5-エン、1-メチルビグアニド、1-エチルビグアニド、1-n-ブチルビグアニド、1-n-オクタデシルビグアニド、1,1-ジメチルビグアニド、1,1-ジエチルビグアニド、1-シクロヘキシルビグアニド、1-アリルビグアニド、1-フェニルビグアニド、1-(o-トリル)ビグアニド等のグアニジン系化合物;テトラフェニルホスホニウムブロマイド、テトラブチルホスホニウムブロマイド、ブチルトリフェニルホスホニウムブロマイド、テトラフェニルホスホニウムイオダイド、テトラブチルホスホニウムイオダイド、ブチルトリフェニルホスホニウムイオダイド、テトラフェニルホスホニウムテトラフェニルボレート、テトラブチルホスホニウムテトラフェニルボレート、ブチルトリフェニルホスホニウムテトラフェニルボレート、テトラフェニルホスホニウムテトラブチルボレート、テトラブチルホスホニウムテトラブチルボレート、ブチルトリフェニルホスホニウムテトラブチルボレート、テトラフェニルホスホニウムアセテート、テトラブチルホスホニウムアセテート、ブチルトリフェニルホスホニウムアセテート、テトラブチルホスホニウムテトラフルオロボレート、テトラブチルホスホニウムヘキサフルオロホスフェート、メチルトリブチルホスホニウムジメチルホスフェート、テトラブチルホスホニウムアセテート、テトラブチルホスホニウムヒドロキシド等のホスホニウム系化合物:チタンやコバルト等の遷移金属を含む化合物;等が挙げられる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。
(Curing accelerator (curing catalyst))
The curable resin composition of the present invention may contain a curing accelerator (curing catalyst) for accelerating curing of the epoxy resin and the curing agent. Examples of the curing accelerator include, but are not particularly limited to, amine-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, phosphonium-based curing accelerators, and the like. These may be used individually by 1 type, and may be used in combination of 2 or more types. For example, aliphatic tertiary amines such as triethylamine, tripropylamine, tributylamine, dimethylbutylamine, dimethylpentylamine, dimethylcyclohexylamine, dimethylbenzylamine, dimethylaminomethylphenol, dimethylamino-p-cresol, piperidine, α- picoline, pyridine, 4-dimethylaminopyridine, 2,4,6-tris(dimethylaminomethyl)phenol, 3,4,5-tris(dimethylaminomethyl)phenol, 2-methylimidazole, 2-ethyl-4-methyl imidazole, 2-undecylimidazole, 2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, N-aminoethylpiperazine, 1,3,6-trisaminomethylhexane, m-xylylenediamine, p-xylylenediamine, N-(2-aminoethyl)piperazine, m-phenylenediamine, p-phenylenediamine, diaminodiphenylmethane, methylenedianiline, 2, 4-toluenediamine, 2,4-diaminoanisole, 2,4-toluenediamine, 2,4-diaminodiphenylamine, 4,4′-methylenedianiline, 1,3-diaminocyclohexane, 3,9-bis(3 -aminopropyl)-2,4,8,10-tetrapyro[5,5]undecane, 1,8-diazabicyclo[5,4,0]undecene-7,1,5-diazabicyclo(4,3,0)- Amine compounds such as nonene, polyamine, polyamidoamine, polyamide, modified polyamine, modified polyamidoamine, modified polyamide; dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o -tolyl)guanidine, dimethylguanidine, diphenylguanidine, di(o-tolyl)guanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]deca-5- Ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecyl Guanidine compounds such as biguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, 1-(o-tolyl)biguanide; tetraphenylphosphonium bromide, Tetrabutylphosphonium bromide, butyltriphenylphosphonium bromide, tetraphenylphosphonium iodide, tetrabutylphosphonium iodide, butyltriphenylphosphonium iodide, tetraphenylphosphonium tetraphenylborate, tetrabutylphosphonium tetraphenylborate, butyltriphenylphosphonium tetraphenyl Borate, tetraphenylphosphonium tetrabutylborate, tetrabutylphosphonium tetrabutylborate, butyltriphenylphosphonium tetrabutylborate, tetraphenylphosphonium acetate, tetrabutylphosphonium acetate, butyltriphenylphosphonium acetate, tetrabutylphosphonium tetrafluoroborate, tetrabutylphosphonium Phosphonium compounds such as hexafluorophosphate, methyltributylphosphonium dimethylphosphate, tetrabutylphosphonium acetate and tetrabutylphosphonium hydroxide; compounds containing transition metals such as titanium and cobalt; These may be used individually by 1 type, and may be used in combination of 2 or more types.
(反応性希釈剤)
本発明の硬化性樹脂組成物は、導電性樹脂組成物の粘度調整や硬化性調整等のための反応性希釈剤を含有していてもよい。反応性希釈剤としては、特に限定されないが、分子構造中にエポキシ基を1つ有する化合物、分子構造中にオキセタン基を1つ以上有する化合物等の1種以上が挙げられる。例えば、グリシジルフェニルエーテル、グリシジルラウリルエーテル、2-フェニルフェノールグリシジルエーテル、アリルグリシジルエーテル、4-tertブチルフェニルグリシジルエーテル、N-グリシジルフタルイミド、2-エチルヘキシルグリシジルエーテル、2-エチルヘキシルグリシジルエーテル、三菱ケミカル社製のYED111N、YED111AN、YED188、ADEKA社製のアデカグリシロールED-502、アデカグリシロールED-502S、アデカグリシロールED-509E、アデカグリシロールED-509S、アデカグリシロールED-529、ナガセケムテックス社製のデナコールEX-145、デナコールEX-171、デナコールEX-192、共栄社化学社製のエポライトM-1230、エポライト100MF、東亜合成社製のアロンオキセタンOXT-101、アロンオキセタンOXT-212、アロンオキセタンOXT-121、アロンオキセタンOXT-221、UBE社製のETERNACOLL EHO、ETERNACOLL HBOX、ETERNACOLL OXMA、ETERNACOLL OXBP等が挙げられる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。
(reactive diluent)
The curable resin composition of the present invention may contain a reactive diluent for adjusting the viscosity and curability of the conductive resin composition. Examples of the reactive diluent include, but are not limited to, one or more compounds having one epoxy group in the molecular structure, compounds having one or more oxetane groups in the molecular structure, and the like. For example, glycidyl phenyl ether, glycidyl lauryl ether, 2-phenylphenol glycidyl ether, allyl glycidyl ether, 4-tertbutylphenyl glycidyl ether, N-glycidyl phthalimide, 2-ethylhexyl glycidyl ether, 2-ethylhexyl glycidyl ether, manufactured by Mitsubishi Chemical Corporation. YED111N, YED111AN, YED188, ADEKA's ADEKA GLYCIROL ED-502, ADEKA GLYCIROL ED-502S, ADEKA GLYCIROL ED-509E, ADEKA GLYCIROL ED-509S, ADEKA GLYCIROL ED-529, Nagase ChemteX Corporation Denacol EX-145, Denacol EX-171, Denacol EX-192 manufactured by Kyoeisha Chemical Co., Ltd., Epolite M-1230, Epolite 100MF manufactured by Kyoeisha Chemical Co., Ltd., Aron Oxetane OXT-101, Aron Oxetane OXT-212, Aron Oxetane OXT manufactured by Toagosei Co., Ltd. -121, Aronoxetane OXT-221, ETERNACOLL EHO manufactured by UBE, ETERNACOLL HBOX, ETERNACOLL OXMA, ETERNACOLL OXBP, and the like. These may be used individually by 1 type, and may be used in combination of 2 or more types.
(導電性粉末)
本発明の導電性樹脂組成物は、錫粉末以外の導電性粉末を含んでいてもよい。このような導電性粉末としては、例えば、無鉛ハンダ粉末、金粉末、金合金粉末、銀粉末、銀合金粉末、銅粉末、銅合金粉末、銀被覆銅粉末、銀被覆銅合金粉末、銀被覆シリカ粉末、銀被覆ニッケル粉末、銀被覆アルミニウム粉末、銀被覆チタン酸カリウム粉末、銀被覆カーボン粉末、樹脂コア金属被覆微粒子、ニッケル粉末、導電性カーボン粉末、カーボンナノチューブ、グラフェン等からなる群より選ばれる1種以上が挙げられる。
例えば、無鉛ハンダ粉末としては、作業者、使用者、環境等への影響から、不可避的に含まれる量以上の鉛を含有しないハンダの粉末であれば、特に限定されない。無鉛ハンダ粉末の融点は、好ましくは300℃以下であり、より好ましくは240℃以下であり、さらに好ましくは50~240℃である。無鉛ハンダ粉末の融点が300℃を超えると、回路基板や電子部品等の被接続部材が熱破壊や熱劣化するおそれがある。融点が50℃未満であると、機械的強度が弱くなり、導電接続の信頼性が低下するおそれがある。
(Conductive powder)
The conductive resin composition of the present invention may contain conductive powder other than tin powder. Examples of such conductive powder include lead-free solder powder, gold powder, gold alloy powder, silver powder, silver alloy powder, copper powder, copper alloy powder, silver-coated copper powder, silver-coated copper alloy powder, and silver-coated silica. 1 selected from the group consisting of powder, silver-coated nickel powder, silver-coated aluminum powder, silver-coated potassium titanate powder, silver-coated carbon powder, resin core metal-coated fine particles, nickel powder, conductive carbon powder, carbon nanotube, graphene, etc. species or more.
For example, the lead-free solder powder is not particularly limited as long as it does not contain more than the amount of lead that is unavoidably contained in view of the effects on workers, users, the environment, and the like. The melting point of the lead-free solder powder is preferably 300°C or lower, more preferably 240°C or lower, and still more preferably 50 to 240°C. If the melting point of the lead-free solder powder exceeds 300° C., the members to be connected such as circuit boards and electronic parts may be thermally destroyed or deteriorated. If the melting point is less than 50° C., the mechanical strength may be weak and the reliability of conductive connection may be lowered.
(樹脂)
本発明の導電性樹脂組成物は、エポキシ樹脂以外の樹脂を含んでいてもよい。このような樹脂としては、熱可塑性樹脂又は熱硬化性樹脂のいずれでもよく、1種又は2種以上を用いることができる。
熱可塑性樹脂としては、例えば、ポリビニルブチラール系樹脂、アクリル系樹脂、ポリエステル系樹脂、フェノキシ樹脂、ポリイミド系樹脂、ポリオレフィン系樹脂、熱可塑性ポリウレタン系樹脂、ポリアミド系樹脂、ポリカーボネート系樹脂、ポリフェニレンエーテル系樹脂、ポリビニルエーテル系樹脂、ポリビニルアルコール系樹脂、ポリ酢酸ビニル系樹脂、アイオノマー樹脂、ポリビニルピロリドン系樹脂、テルペン系樹脂等からなる群より選ばれる1種以上が挙げられる。
熱硬化性樹脂としては、例えば、レゾール型フェノール系樹脂、ポリイミド系樹脂、キシレン系樹脂、ポリウレタン系樹脂、メラミン系樹脂、ウレア系樹脂、フラン樹脂、イソシアネート系樹脂、尿素樹脂等からなる群より選ばれる1種以上が挙げられる。
本発明においては、樹脂としてポリビニルブチラール系樹脂、レゾール型フェノール系樹脂、アクリル系樹脂、ポリエステル系樹脂、フェノキシ樹脂、ポリイミド系樹脂及びキシレン系樹脂からなる群より選ばれる1種以上を含むことが好ましい。これらの中でも、膜形成状態、接続信頼性、基材への密着性等の観点から、ポリビニルブチラール系樹脂が好適に用いられる。
(resin)
The conductive resin composition of the present invention may contain resins other than epoxy resins. As such a resin, either a thermoplastic resin or a thermosetting resin may be used, and one or more of them may be used.
Examples of thermoplastic resins include polyvinyl butyral resins, acrylic resins, polyester resins, phenoxy resins, polyimide resins, polyolefin resins, thermoplastic polyurethane resins, polyamide resins, polycarbonate resins, and polyphenylene ether resins. , polyvinyl ether-based resins, polyvinyl alcohol-based resins, polyvinyl acetate-based resins, ionomer resins, polyvinylpyrrolidone-based resins, terpene-based resins, and the like.
As the thermosetting resin, for example, selected from the group consisting of resol-type phenolic resins, polyimide resins, xylene resins, polyurethane resins, melamine resins, urea resins, furan resins, isocyanate resins, urea resins, and the like. 1 or more types are included.
In the present invention, the resin preferably contains one or more selected from the group consisting of polyvinyl butyral resin, resol-type phenol resin, acrylic resin, polyester resin, phenoxy resin, polyimide resin and xylene resin. . Among these, polyvinyl butyral-based resins are preferably used from the viewpoint of film formation state, connection reliability, adhesion to substrates, and the like.
(酸化防止剤)
本発明の導電性樹脂組成物は、酸化防止剤を含んでいてもよい。これにより、導電性樹脂組成物の硬化物の耐熱性や耐黄変性等の向上に寄与することができる。酸化防止剤としては、酸化防止機能を有する化合物であれば特に限定されず、公知又は慣用の酸化防止剤が使用できる。例えば、ヒンダードフェノール化合物等のフェノール系酸化防止剤、ハイドロキノン等のキノン系酸化防止剤、リン系酸化防止剤、イオウ系酸化防止剤、ヒンダードアミン化合物等のヒンダードアミン系酸化防止剤等が挙げられる。これらは、1種を単独で用いてもよく、2種以上組み合わせて用いてもよい。例えば、2,2-メチレン-ビス(4-メチル-6-tert-ブチルフェノール)、カテコール、tert-ブチルカテコール、2-ブチル-4-ヒドロキシアニソール、2,6-ジ-tert-ブチル-p-クレゾール、2,4-ジ-tert-ブチル-6-メチルフェノール、2-tert-ブチル-4-メチルフェノール、2,4-ジ-tert-ブチルフェノール、2,4-ジ-tert-ペンチルフェノール、ビス-[3,3-ビス-(4'-ヒドロキシ-3'-tert-ブチルフェニル)-ブタノイックアシッド]-グリコールエステル、2-tert-ブチル-6-(3-tert-ブチル-2-ヒドロキシ-5-メチルベンジル)-4-メチルフェニルアクリレート、2-[1-(2-ヒドロキシ-3,5-ジ-tert-ペンチルフェニル)エチル]-4,6-ジ-tert-ペンチルフェニルアクリレート、4,4′-ブチリデンビス(6-tert-ブチル-3-メチルフェノール)、2,2'-ブチリデンビス(4,6-ジ-tert-ブチルフェノール)、4,4′-チオビス(6-tert-ブチル-3-メチルフェノール)、3,9-ビス[2-[3-(3-tert-ブチル-4-ヒドロキシ-5-メチルフェニル)プロピオニロキシ]-1,1-ジメチルエチル]-2,4,8,10-テトラオキサスピロ[5,5]ウンデカン、ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]、チオジエチレンビス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート]、オクタデシル-3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート、N,N′-ヘキサン-1,6-ジイルビス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオンアミド]、ベンゼンプロパン酸,3,5-ビス(1,1-ジメチルエチル)-4-ヒドロキシ,C7-C9側鎖アルキルエステル、2,4-ジメチル-6-(1-メチルペンタデシル)フェノール、ジエチル[[3,5-ビス(1,1-ジメチルエチル)-4-ヒドロキシフェニル]メチル]フォスフォネート、3,3′,3″,5,5′,5″-ヘキサ-tert-ブチル-a,a′,a″-(メシチレン-2,4,6-トリル)トリ-p-クレゾール、カルシウムジエチルビス[[3,5-ビス(1,1-ジメチルエチル)-4-ヒドロキシフェニル]メチル]フォスフォネート、4,6-ビス(オクチルチオメチル)-o-クレゾール、エチレンビス(オキシエチレン)ビス[3-(5-tert-ブチル-4-ヒドロキシ-m-トリル)プロピオネート]、トリエチレングリコール-ビス[3-(3-tert-ブチル-5-メチル-4-ヒドロキシフェニル)プロピオネート]、ヘキサメチレンビス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート、1,3,5-トリメチル-2,4,6-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)ベンゼン、1,3,5-トリス(3,5-ジ-tert-ブチル-4-ヒドロキシベンジル)-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、1,3,5-トリス[(4-tert-ブチル-3-ヒドロキシ-2,6-キシリル)メチル]-1,3,5-トリアジン-2,4,6(1H,3H,5H)-トリオン、N-フェニルベンゼンアミンと2,4,6-トリメチルペンテンとの反応生成物、2,6-ジ-tert-ブチル-4-(4,6-ビス(オクチルチオ)-1,3,5-トリアジン-2-イルアミノ)フェノール、ピクリン酸、クエン酸等のフェノール系酸化防止剤;β-ナフトキノン、2-メトキシ-1,4-ナフトキノン、メチルハイドロキノン、ハイドロキノン、ハイドロキノンモノメチルエーテル、モノ-tert-ブチルハイドロキノン、2,5-ジ-tert-ブチルハイドロキノン、p-ベンゾキノン、2,5-ジフェニル-p-ベンゾキノン、2,5-ジ-tert-ブチル-p-ベンゾキノン等のキノン系酸化防止剤;トリス(2,4-ジ-tert-ブチルフェニル)フォスファイト、トリス[2-[[2,4,8,10-テトラ-tert-ブチルジベンゾ[d,f][1,3,2]ジオキサフォスフェフィン-6-イル]オキシ]エチル]アミン、ビス(2,4-ジ-tert-ブチルフェニル)ペンタエリスリートールジフォスファイト、ビス[2,4-ビス(1,1-ジメチルエチル)-6-メチルフェニル]エチルエステル亜リン酸、テトラキス(2,4-ジ-tert-ブチルフェニル)[1,1-ビスフェニル]-4,4′-ジイルビスホスフォナイト、6-[3-(3-tert-ブチル-4-ヒドロキシ-5-メチルフェニル)プロポキシ]-2,4,8,10-テトラ-tert-ブチルジベンズ[d、f][1,3,2]ジオキサフォスフェフィン等のリン系酸化防止剤;ジラウリル3,3′-チオジプロピオネート、ジミリスチル3,3′-チオジプロピオネート、ジステアリル3,3’-チオジプロピオネート、ペンタエリスリチルテトラキス(3-ラウリルチオプロピオネート)、2-メルカプトベンズイミダゾール等のイオウ系酸化防止剤;フェノチアジン等のアミン系酸化防止剤;ラクトン系酸化防止剤;ビタミンE系酸化防止剤等からなる群より選ばれる1種以上が挙げられる。
酸化防止剤は、市販品を用いてもよい。例えば、BASF社製のIRGANOXシリーズ、ADEKA社製のアデカスタブシリーズ、精工化学社製のノンフレックスシリーズ、住友化学社製のSumilizerシリーズ等が挙げられる。
(Antioxidant)
The conductive resin composition of the present invention may contain an antioxidant. This can contribute to improvement in heat resistance, yellowing resistance, etc. of the cured product of the conductive resin composition. The antioxidant is not particularly limited as long as it is a compound having an antioxidant function, and known or commonly used antioxidants can be used. Examples thereof include phenol antioxidants such as hindered phenol compounds, quinone antioxidants such as hydroquinone, phosphorus antioxidants, sulfur antioxidants, and hindered amine antioxidants such as hindered amine compounds. These may be used individually by 1 type, and may be used in combination of 2 or more types. For example, 2,2-methylene-bis(4-methyl-6-tert-butylphenol), catechol, tert-butylcatechol, 2-butyl-4-hydroxyanisole, 2,6-di-tert-butyl-p-cresol , 2,4-di-tert-butyl-6-methylphenol, 2-tert-butyl-4-methylphenol, 2,4-di-tert-butylphenol, 2,4-di-tert-pentylphenol, bis- [3,3-bis-(4′-hydroxy-3′-tert-butylphenyl)-butanoic acid]-glycol ester, 2-tert-butyl-6-(3-tert-butyl-2-hydroxy- 5-methylbenzyl)-4-methylphenyl acrylate, 2-[1-(2-hydroxy-3,5-di-tert-pentylphenyl)ethyl]-4,6-di-tert-pentylphenyl acrylate, 4, 4′-butylidenebis(6-tert-butyl-3-methylphenol), 2,2′-butylidenebis(4,6-di-tert-butylphenol), 4,4′-thiobis(6-tert-butyl-3- methylphenol), 3,9-bis[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethyl]-2,4,8, 10-tetraoxaspiro[5,5]undecane, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], thiodiethylenebis[3-(3,5-di- tert-butyl-4-hydroxyphenyl)propionate], octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, N,N′-hexane-1,6-diylbis[3-( 3,5-di-tert-butyl-4-hydroxyphenyl)propionamide], benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy, C 7 -C 9 side chain alkyl ester , 2,4-dimethyl-6-(1-methylpentadecyl)phenol, diethyl [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]phosphonate, 3,3′ ,3″,5,5′,5″-hexa-tert-butyl-a,a′,a″-(mesitylene-2,4,6-tolyl)tri-p-cresol, calcium diethylbis[[3, 5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]phosphonate, 4,6-bis(octylthiomethyl)-o-cresol, ethylenebis(oxyethylene)bis[3-(5 -tert-butyl-4-hydroxy-m-tolyl)propionate], triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], hexamethylenebis[3-( 3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,3 ,5-tris[(4-tert-butyl-3-hydroxy-2,6-xylyl)methyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, N- Reaction product of phenylbenzenamine and 2,4,6-trimethylpentene, 2,6-di-tert-butyl-4-(4,6-bis(octylthio)-1,3,5-triazine-2- Phenolic antioxidants such as ylamino)phenol, picric acid, and citric acid; -quinone antioxidants such as di-tert-butyl hydroquinone, p-benzoquinone, 2,5-diphenyl-p-benzoquinone, 2,5-di-tert-butyl-p-benzoquinone; -tert-butylphenyl)phosphite, tris[2-[[2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphefin-6-yl ]oxy]ethyl]amine, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis[2,4-bis(1,1-dimethylethyl)-6-methylphenyl]ethyl ester phosphorous acid, tetrakis(2,4-di-tert-butylphenyl)[1,1-bisphenyl]-4,4′-diylbisphosphonite, 6-[3-(3-tert-butyl- Phosphorus-based antioxidants such as 4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenz[d,f][1,3,2]dioxaphosphefin; Dilauryl 3,3′-thiodipropionate, Dimyristyl 3,3′-thiodipropionate, Distearyl 3,3′-thiodipropionate, Pentaerythrityl tetrakis(3-laurylthiopropionate), 2- One or more selected from the group consisting of sulfur-based antioxidants such as mercaptobenzimidazole; amine-based antioxidants such as phenothiazine; lactone-based antioxidants; and vitamin E-based antioxidants.
A commercially available product may be used as the antioxidant. Examples thereof include the IRGANOX series manufactured by BASF, the Adekastab series manufactured by ADEKA, the Nonflex series manufactured by Seiko Chemical Co., Ltd., and the Sumilizer series manufactured by Sumitomo Chemical.
<導電性樹脂組成物の性状>
本発明の導電性樹脂組成物の性状は、粉末状、固体状、ペースト状、液体状(ワニス状)等の任意の性状とすることができる。導電性インク、導電性接着剤、回路接続材料としての用途の際には、室温(25℃)でペースト状又は液体状(ワニス状)であることが好適である。
本発明の導電性樹脂組成物は、材料をミキサー等により混合、撹拌してペースト状又は液体状(ワニス状)の導電性樹脂組成物を作製した際に、ダマ等の発生がなく、均一な導電性樹脂組成物を形成することができる。
<Properties of the conductive resin composition>
The properties of the conductive resin composition of the present invention can be any of powder, solid, paste, liquid (varnish), and the like. When used as a conductive ink, a conductive adhesive, or a circuit connecting material, it is preferably in the form of paste or liquid (varnish) at room temperature (25°C).
When the conductive resin composition of the present invention is mixed and stirred with a mixer or the like to prepare a paste-like or liquid-like (varnish-like) conductive resin composition, there is no generation of lumps and the like, and it is uniform. A conductive resin composition can be formed.
<導電性樹脂組成物の特性>
本発明の導電性樹脂組成物は、硬化性に優れている。例えば、基材の上に塗布後に、50℃~250℃で5分~300分熱処理(焼成)することで、容易に導電膜(乾燥塗膜)を形成することができる。
本発明の導電性樹脂組成物は、硬化物とした際の表面は絶縁性を示すものの、内部は良好な導電性を示す。例えば、導電性樹脂組成物を用いて接続部材を接合した際に、導電性樹脂組成物の膜は表面絶縁性(体積抵抗率が1.0×10-1Ω・cm以上であり、表面が実質的に絶縁体となっている)にもかかわらず、内部が導電性を示すことから、接続部材間に導電接続を形成することが可能である。ここで、導電接続の形成の確認は、実施例において記載したLED点灯試験により確認することができる。これより、導電性樹脂組成物の硬化物は、表面が絶縁性、内部が導電性を示す、絶縁皮膜付き電線のような構造を形成していると考えられる。
本発明の導電性樹脂組成物は、各種の基材に対する密着性に優れている。例えば、ガラス、金属又はプラスチック(例えば、ポリエステル等)に対する密着性に優れている。
本発明の導電性樹脂組成物は、製造後に保存した後であっても、塗布・印刷等を行うことが可能な実用的な保存安定性を有している。
<Characteristics of the conductive resin composition>
The conductive resin composition of the present invention has excellent curability. For example, a conductive film (dry coating film) can be easily formed by heat-treating (baking) at 50° C. to 250° C. for 5 minutes to 300 minutes after coating on a substrate.
When the conductive resin composition of the present invention is cured, the surface exhibits insulating properties, but the interior exhibits good electrical conductivity. For example, when the connection member is joined using the conductive resin composition, the film of the conductive resin composition has surface insulation (volume resistivity is 1.0 × 10 -1 Ω cm or more, and the surface is In spite of the fact that they are substantially insulating), it is possible to form an electrically conductive connection between the connecting members, since the interior is electrically conductive. Here, confirmation of the formation of the conductive connection can be confirmed by the LED lighting test described in the examples. From this, it is considered that the cured product of the conductive resin composition forms a structure like an electric wire with an insulating film, in which the surface is insulating and the inside is conductive.
The conductive resin composition of the present invention has excellent adhesion to various substrates. For example, it has excellent adhesion to glass, metal or plastic (eg, polyester, etc.).
The conductive resin composition of the present invention has practical storage stability that allows coating, printing, etc., even after storage after production.
<導電性樹脂組成物の調製方法>
本発明の導電性樹脂組成物の調製に際しては、錫粉末、エポキシ樹脂、有機酸化合物及びチオール系硬化剤を必須成分とし、必要に応じて無鉛ハンダ粉末、溶媒等を、任意の順序で混合容器に加えて混合し製造することができる。混合に際しては、例えば、自転・公転ミキサー、ボールミル、ロールミル、ビーズミル、プラネタリーミキサー、タンブラー、スターラー、撹拌機、メカニカルホモジナイザー、超音波ホモジナイザー、高圧ホモジナイザー、ペイントシェーカー、V型ブレンダー、ナウターミキサー、バンバリーミキサー、混練ロール、一軸押出機、二軸押出機等で混合する方法が適宜用いられる。
導電性樹脂組成物を調製する際の温度(各成分を混合する際の温度)は、特に限定されない。必要に応じて、加熱等をすることもでき、例えば、10~100℃で導電性樹脂組成物を調製することができる。
導電性樹脂組成物を調製する際の雰囲気は、特に限定されない。大気中で行うことができ、不活性雰囲気下で行うこともできる。
<Method for preparing conductive resin composition>
When preparing the conductive resin composition of the present invention, tin powder, epoxy resin, organic acid compound and thiol-based curing agent are essential components, and if necessary, lead-free solder powder, solvent, etc. are added in any order in a mixing container. can be produced by mixing in addition to For mixing, for example, rotation/revolution mixer, ball mill, roll mill, bead mill, planetary mixer, tumbler, stirrer, stirrer, mechanical homogenizer, ultrasonic homogenizer, high pressure homogenizer, paint shaker, V-type blender, Nauta mixer, Banbury A method of mixing with a mixer, a kneading roll, a single-screw extruder, a twin-screw extruder, or the like is appropriately used.
The temperature when preparing the conductive resin composition (temperature when mixing each component) is not particularly limited. If necessary, heating or the like can be performed, and for example, the conductive resin composition can be prepared at 10 to 100°C.
The atmosphere in preparing the conductive resin composition is not particularly limited. It can be carried out in the atmosphere, or it can be carried out under an inert atmosphere.
<導電性樹脂組成物の用途>
本発明の導電性樹脂組成物の用途は、導電性物体の製造に係る用途である。導電性物体は、導電性樹脂組成物に加えて他の部材等を含んでいてもよい。
導電性物体としては、例えば、導電性インク、回路接続材料、導電性ペースト、導電性を有する膜、導電性繊維、導電性塗料、半導体パッケージ用導電材料、マイクロエレクトロニクスデバイス用導電材料、帯電防止材料、電磁波シールド材料、導電性接着剤(ダイ取付接着剤等、表面実装部品取付用接着剤)、ダイアタッチペースト、アクチュエータ、センサー、導電性樹脂成形体、電子部品の電極形成材料(チップ抵抗の端子等)、電子部品の内部電極用材料(MLCCの内部電極等)、集電極材料、アンテナ形成材料等からなる群より選ばれる1種以上が挙げられる。
<Use of the conductive resin composition>
The use of the conductive resin composition of the present invention is for the production of conductive objects. The conductive object may contain other members in addition to the conductive resin composition.
Examples of conductive substances include conductive inks, circuit connection materials, conductive pastes, conductive films, conductive fibers, conductive paints, conductive materials for semiconductor packages, conductive materials for microelectronic devices, and antistatic materials. , electromagnetic wave shielding materials, conductive adhesives (die mounting adhesives, adhesives for mounting surface mount components), die attach pastes, actuators, sensors, conductive resin moldings, electrode forming materials for electronic components (terminals for chip resistors etc.), materials for internal electrodes of electronic parts (such as internal electrodes of MLCC), materials for collector electrodes, materials for forming antennas, and the like.
例えば、溶媒を導電性樹脂組成物の成分とすることで、導電性インク、導電性ペースト、導電性塗料、導電性接着剤等を構成することができる。その際の粘度は特に限定されず、用途等に応じて低粘度のワニス状から高粘度のペースト状等とすることができる。
例えば、必要に応じて溶媒等を含む導電性樹脂組成物を、キャスティング法、ディッピング法、バーコート法、ディスペンサ法、ロールコート法、グラビアコート法、グラビア印刷、スクリーン印刷、フレキソ印刷、スプレーコート法、スピンコート法、インクジェット法、オフセット印刷、グラビアオフセット印刷、スリットコート法、ナイフコート法、パッド印刷、樹脂凸印刷、アプリケータ法、反転印刷、反転オフセット印刷等により各種の基材に塗布し、300℃以下の温度で加熱乾燥させて導電性を有する膜とすることができる。乾燥時の雰囲気は、大気中、不活性ガス中、真空中、減圧等からなる群より選ばれる1種以上が挙げられる。特に、導電性を有する膜の劣化抑制(錫粉末等の酸化防止等)の観点からは、窒素、アルゴン等の不活性ガス雰囲気が好ましい。
For example, by using the solvent as a component of the conductive resin composition, conductive ink, conductive paste, conductive paint, conductive adhesive, etc. can be formed. The viscosity at that time is not particularly limited, and it can be in the form of a low-viscosity varnish or a high-viscosity paste or the like depending on the application.
For example, a conductive resin composition containing a solvent or the like as necessary is subjected to a casting method, a dipping method, a bar coating method, a dispenser method, a roll coating method, a gravure coating method, a gravure printing method, a screen printing method, a flexographic printing method, or a spray coating method. , Spin coating method, inkjet method, offset printing, gravure offset printing, slit coating method, knife coating method, pad printing, resin relief printing, applicator method, reverse printing, reverse offset printing, etc. A conductive film can be obtained by heating and drying at a temperature of 300° C. or less. Atmosphere during drying includes one or more selected from the group consisting of air, inert gas, vacuum, reduced pressure, and the like. In particular, an atmosphere of an inert gas such as nitrogen or argon is preferable from the viewpoint of suppressing deterioration of the conductive film (preventing oxidation of tin powder, etc.).
本発明の導電性樹脂組成物は、押出成形、射出成形、圧縮成形、真空成形、圧空成形、真空圧空成形、ブロー成形、TOM成形、プレス成形、インサート成形、インモールド成形等の成形方法により成形し、成形体として用いることができる。成形体としては、例えば電子機器部品、自動車用部品、機械機構部品、食品容器、フィルム、シート、繊維等が挙げられる。 The conductive resin composition of the present invention is molded by molding methods such as extrusion molding, injection molding, compression molding, vacuum molding, pressure molding, vacuum pressure molding, blow molding, TOM molding, press molding, insert molding, and in-mold molding. and can be used as a molded product. Examples of molded articles include electronic device parts, automobile parts, machine mechanism parts, food containers, films, sheets, and fibers.
[導電膜]
本発明の導電膜は、前記導電性樹脂組成物から形成され、体積抵抗率が1.0×10-2Ω・cm未満である。好ましくは導電膜の体積抵抗率が1.0×10-3Ω・cm未満、より好ましくは3.0×10-4Ω・cm以下である。本発明の導電膜は、1.0×10-4Ω・cm未満(10-5Ω・cmオーダー)という、銀ペーストから形成された導電膜に匹敵する体積抵抗率とすることも可能である。
ここで、体積抵抗率は、実施例において記載した方法により得られる。
[Conductive film]
The conductive film of the present invention is formed from the conductive resin composition and has a volume resistivity of less than 1.0×10 −2 Ω·cm. The conductive film preferably has a volume resistivity of less than 1.0×10 −3 Ω·cm, more preferably 3.0×10 −4 Ω·cm or less. The conductive film of the present invention can also have a volume resistivity of less than 1.0×10 −4 Ω·cm (on the order of 10 −5 Ω·cm), which is comparable to a conductive film formed from silver paste. .
Here, the volume resistivity is obtained by the method described in Examples.
導電性樹脂組成物から導電膜を形成する方法としては、特に限定されない。例えば、前記導電性樹脂組成物を溶媒含有のものとし、これを任意の基材上に塗布し乾燥等することで、導電膜を形成できる。また、剥離性基材の上に導電性樹脂組成物を流延又は塗布し乾燥等した後に剥離して得ることができる。
導電膜の形成条件は、特に限定されず、被塗物等に応じて適宜設定できる。導電性樹脂組成物を塗布した後の乾燥等に際しての温度は、例えば50℃以上、好ましくは90℃以上であり、例えば250℃以下、好ましくは220℃以下である。乾燥等の時間としては、例えば5分以上、好ましくは7分以上であり、例えば300分以下、好ましくは200分以下である。
導電膜の乾燥膜厚は、特に限定されず、用途等に応じて適宜調整できる。例えば、10μm以上、好ましくは30μm以上であり、例えば1000μm以下、好ましくは500μm以下である。
A method for forming a conductive film from a conductive resin composition is not particularly limited. For example, a conductive film can be formed by making the conductive resin composition containing a solvent, coating it on an arbitrary substrate, and drying it. Alternatively, it can be obtained by casting or coating a conductive resin composition on a peelable substrate, drying the composition, and then peeling it off.
Conditions for forming the conductive film are not particularly limited, and can be appropriately set according to the object to be coated and the like. The temperature for drying after applying the conductive resin composition is, for example, 50° C. or higher, preferably 90° C. or higher, and is, for example, 250° C. or lower, preferably 220° C. or lower. The drying time is, for example, 5 minutes or more, preferably 7 minutes or more, and is, for example, 300 minutes or less, preferably 200 minutes or less.
The dry film thickness of the conductive film is not particularly limited, and can be appropriately adjusted depending on the application. For example, it is 10 μm or more, preferably 30 μm or more, and for example, 1000 μm or less, preferably 500 μm or less.
[導電性インク]
本発明の導電性インクは、前記導電性樹脂組成物を含むものである。例えば、前記導電性樹脂組成物を、必要に応じて前記溶媒に溶解及び/又は分散させて得ることができる。
導電性インクは、必要に応じて、溶媒、チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤、密着性付与剤、粘弾性調整剤、湿潤分散剤、硬化促進剤(硬化触媒)、反応性希釈剤、錫粉末以外の導電性粉末、エポキシ樹脂以外の樹脂、酸化防止剤、顔料、充填剤(フィラー)、腐食抑制剤、消泡剤、カップリング剤、沈降防止剤等、レベリング剤、重金属不活性化剤、界面活性剤、pH調整剤、紫外線吸収剤、難燃剤、接着付与剤等からなる群より選ばれる1種以上をさらに含んでいてもよい。
導電性インクは、前記成分を混合容器に入れた後に、自転・公転ミキサー、ボールミル、ロールミル、ビーズミル、プラネタリーミキサー、タンブラー、スターラー、撹拌機、メカニカルホモジナイザー、超音波ホモジナイザー、高圧ホモジナイザー、ペイントシェーカー、V型ブレンダー、ナウターミキサー、バンバリーミキサー、混練ロール、一軸押出機、二軸押出機等からなる群より選ばれる1種以上の混合機を用いて混合し、ワニス状又はペースト状とすることで得られる。
[Conductive ink]
The conductive ink of the present invention contains the conductive resin composition. For example, the conductive resin composition can be obtained by dissolving and/or dispersing it in the solvent, if necessary.
If necessary, the conductive ink may contain a solvent, a curing agent for curing epoxy resins other than a thiol-based curing agent, an adhesion imparting agent, a viscoelasticity modifier, a wetting and dispersing agent, a curing accelerator (curing catalyst), a reactive Diluents, conductive powders other than tin powders, resins other than epoxy resins, antioxidants, pigments, fillers, corrosion inhibitors, antifoaming agents, coupling agents, anti-settling agents, leveling agents, heavy metals It may further contain one or more selected from the group consisting of deactivators, surfactants, pH adjusters, UV absorbers, flame retardants, adhesion promoters and the like.
After putting the above components into a mixing vessel, the conductive ink is mixed with a rotation/revolution mixer, ball mill, roll mill, bead mill, planetary mixer, tumbler, stirrer, stirrer, mechanical homogenizer, ultrasonic homogenizer, high pressure homogenizer, paint shaker, By mixing using one or more mixers selected from the group consisting of a V-type blender, a Nauta mixer, a Banbury mixer, a kneading roll, a single-screw extruder, a twin-screw extruder, etc., and forming a varnish or paste. can get.
導電性インクは、例えば配線形成用の印刷用導電性インクとして利用できる。導電性インクを各種基材に適用する方法としては、特に限定されない。例えば、前記の導電性樹脂組成物を基材に塗布する方法が挙げられる。本発明においては、例えばスクリーン印刷、インクジェット印刷、フレキソ印刷、グラビア印刷等からなる群より選ばれる1種以上が好ましく、印刷性や形状保持性に優れることから、スクリーン印刷、インクジェット印刷等からなる群より選ばれる1種以上の印刷方法を用いることがより好ましい。
ここで、スクリーン印刷におけるメッシュは適宜選択でき、導電性インク中の導電性粉末や無鉛ハンダ粉末等が過度に除去されないだけのメッシュを採用することが好ましい。
導電性インクを塗布してなる塗布膜の膜厚は、各種の用途に応じて適当な膜厚とすることができる。例えば1μm以上、好ましくは2μm以上、より好ましくは5μm以上であり、500μm以下である。
導電性インクは、導電性、各種基材への密着性、レベリング(表面平滑性)、印刷性等からなる群より選ばれる1種以上の特性に優れたものである。
The conductive ink can be used, for example, as a printing conductive ink for wiring formation. The method of applying the conductive ink to various substrates is not particularly limited. For example, there is a method of applying the conductive resin composition to a substrate. In the present invention, for example, one or more selected from the group consisting of screen printing, inkjet printing, flexographic printing, gravure printing, etc. is preferable, and the group consisting of screen printing, inkjet printing, etc., because it is excellent in printability and shape retention. It is more preferable to use one or more selected printing methods.
Here, the mesh for screen printing can be appropriately selected, and it is preferable to adopt a mesh that does not excessively remove the conductive powder, lead-free solder powder, etc. in the conductive ink.
The film thickness of the coating film formed by applying the conductive ink can be set to an appropriate film thickness according to various uses. For example, it is 1 μm or more, preferably 2 μm or more, more preferably 5 μm or more, and 500 μm or less.
The conductive ink is excellent in one or more properties selected from the group consisting of conductivity, adhesion to various substrates, leveling (surface smoothness), printability, and the like.
[導電性接着剤]
本発明の導電性接着剤は、前記導電性樹脂組成物を含むものである。例えば、前記導電性樹脂組成物を、必要に応じて前記溶媒に溶解及び/又は分散させて得ることができる。
導電性接着剤は、接着対象部位を導電性を有するように接着するために用いられる。例えば、電池、電気・電子機器の製造において、導電性が必要な接着を行う際等に用いられる。導電性接着剤は、必要に応じて、溶媒、チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤、密着性付与剤、粘弾性調整剤、湿潤分散剤、硬化促進剤(硬化触媒)、反応性希釈剤、錫粉末以外の導電性粉末、エポキシ樹脂以外の樹脂、酸化防止剤、顔料、充填剤(フィラー)、腐食抑制剤、消泡剤、カップリング剤、沈降防止剤等、レベリング剤、重金属不活性化剤、界面活性剤、pH調整剤、紫外線吸収剤、難燃剤、接着付与剤等からなる群より選ばれる1種以上をさらに含んでいてもよい。
導電性接着剤は、前記成分を混合容器に入れた後に、自転・公転ミキサー、ボールミル、ロールミル、ビーズミル、プラネタリーミキサー、タンブラー、スターラー、撹拌機、メカニカルホモジナイザー、超音波ホモジナイザー、高圧ホモジナイザー、ペイントシェーカー、V型ブレンダー、ナウターミキサー、バンバリーミキサー、混練ロール、一軸押出機、二軸押出機等からなる群より選ばれる1種以上の混合機を用いて混合し、ワニス状又はペースト状とすることで得られる。
[Conductive adhesive]
The conductive adhesive of the present invention contains the conductive resin composition. For example, the conductive resin composition can be obtained by dissolving and/or dispersing it in the solvent as required.
A conductive adhesive is used to adhere the parts to be adhered so as to have conductivity. For example, in the manufacture of batteries and electric/electronic equipment, it is used for adhesion that requires conductivity. The conductive adhesive may optionally contain a solvent, a curing agent for curing epoxy resins other than thiol-based curing agents, adhesion imparting agents, viscoelasticity modifiers, wetting and dispersing agents, curing accelerators (curing catalysts), reaction diluents, conductive powders other than tin powder, resins other than epoxy resins, antioxidants, pigments, fillers, corrosion inhibitors, antifoaming agents, coupling agents, anti-settling agents, etc., leveling agents, It may further contain one or more selected from the group consisting of heavy metal deactivators, surfactants, pH adjusters, UV absorbers, flame retardants, adhesion promoters and the like.
After putting the above components into a mixing container, the conductive adhesive is mixed with a rotation/revolution mixer, ball mill, roll mill, bead mill, planetary mixer, tumbler, stirrer, stirrer, mechanical homogenizer, ultrasonic homogenizer, high pressure homogenizer, paint shaker. , V-type blender, Nauta mixer, Banbury mixer, kneading roll, single-screw extruder, twin-screw extruder, etc. Mixing using one or more mixers to form a varnish or paste is obtained by
本発明の導電性接着剤は、異方導電性接着剤として用いることができる。これにより、微細化されたICチップ、発光ダイオード等の電子部品、回路基板の電極接続等において、高信頼性の導電接続を形成することができる。また、本発明の導電性接着剤は、硬化させた後の硬化膜表面が絶縁性を示す場合があり、電子部品を高密度に実装させる際に有利である。
本発明の導電性接着剤を介して被接着部材同士が接着されている接着構造体としては、例えば、電極を有する基板にICチップを接着した、ICカードやICタグ等のRFID関連製品や、電極を有する基板に発光ダイオードを接着した発光電子部品等が挙げられる。例えば、基板の少なくとも一方の面に電極を多数形成し、各電極がそれぞれ少なくとも覆われるように本発明の導電性接着剤を塗布して接着剤膜を形成し、各電極部に各電子部品の電極部を相対させて圧着し、接着剤層を硬化させることで、導電性接着剤を用いた接着構造体を形成することができる。
The conductive adhesive of the present invention can be used as an anisotropic conductive adhesive. As a result, highly reliable conductive connections can be formed in miniaturized IC chips, electronic components such as light emitting diodes, electrode connections on circuit boards, and the like. In addition, the conductive adhesive of the present invention may exhibit insulating properties on the surface of the cured film after curing, which is advantageous when electronic components are mounted at high density.
Examples of the adhesive structure in which members to be bonded are bonded via the conductive adhesive of the present invention include, for example, RFID-related products such as IC cards and IC tags in which an IC chip is bonded to a substrate having electrodes, A light-emitting electronic component in which a light-emitting diode is adhered to a substrate having electrodes, and the like can be mentioned. For example, a large number of electrodes are formed on at least one surface of a substrate, the conductive adhesive of the present invention is applied so as to cover at least each electrode to form an adhesive film, and each electronic component is attached to each electrode portion. By pressing the electrode portions against each other and curing the adhesive layer, an adhesive structure using the conductive adhesive can be formed.
本発明の導電性接着剤を基材に塗布する手段は、特に限定されない。例えば、前記の導電性樹脂組成物を基材に塗布する方法が挙げられる。本発明においては、印刷、吐出等により行うことができる。印刷方法としては、例えばスクリーン印刷、インクジェット印刷、フレキソ印刷、グラビア印刷等からなる群より選ばれる1種以上が好ましく、印刷性や形状保持性に優れることから、スクリーン印刷、インクジェット印刷等からなる群より選ばれる1種以上の印刷方法を用いることが好ましい。
ここで、スクリーン印刷におけるメッシュは適宜選択でき、導電性接着剤中の導電性粉末が過度に除去されないだけのメッシュを採用することが好ましい。
導電性接着剤を塗布してなる接着剤膜の膜厚は、各種の用途に応じて適当な膜厚とすることができる。例えば1μm以上、好ましくは2μm以上、より好ましくは5μm以上であり、200μm以下である。
The means for applying the conductive adhesive of the present invention to the substrate is not particularly limited. For example, there is a method of applying the conductive resin composition to a substrate. In the present invention, it can be carried out by printing, discharging, or the like. As the printing method, for example, one or more selected from the group consisting of screen printing, inkjet printing, flexographic printing, gravure printing, etc. is preferable, and the group consisting of screen printing, inkjet printing, etc., because of excellent printability and shape retention. It is preferable to use one or more selected printing methods.
Here, the mesh used in screen printing can be appropriately selected, and it is preferable to adopt a mesh that does not excessively remove the conductive powder in the conductive adhesive.
The film thickness of the adhesive film formed by applying the conductive adhesive can be set to an appropriate film thickness according to various uses. For example, it is 1 μm or more, preferably 2 μm or more, more preferably 5 μm or more, and 200 μm or less.
本発明の導電性接着剤は、フィルム状に成形して用いてもよい。フィルム状の導電性接着剤は、例えば、導電性接着剤組成物に必要に応じて溶剤等を加える等で得られた導電性接着剤溶液を、剥離性支持体上に塗布し、溶剤等を除去する方法により得ることができる。フィルム状の導電性接着剤は、取り扱い等の点から一層便利である。フィルム状の導電性接着剤の層を1層以上と、必要に応じて、1層以上の絶縁性接着剤層、1層以上の剥離性材料層等とともに、多層構造体として用いることもできる。
本発明の導電性接着剤は、通常、加熱及び加圧を併用して被着体同士を接着させることができる。加熱温度は、被着体に損傷を与えない範囲であれば特に制限されず、例えば70℃以上250℃以下である。圧力は、被着体に損傷を与えない範囲であれば特に制限されず、例えば0.1MPa以上10MPa以下である。加熱及び加圧は、例えば0.5秒以上120秒以下で行うことが好ましい。
The conductive adhesive of the present invention may be used in the form of a film. A film-like conductive adhesive is prepared by, for example, applying a conductive adhesive solution obtained by adding a solvent or the like to a conductive adhesive composition as necessary, on a peelable support, and removing the solvent or the like. It can be obtained by a method of removing. A film-like conductive adhesive is more convenient in terms of handling and the like. It can also be used as a multi-layer structure with one or more film-like conductive adhesive layers, optionally one or more insulating adhesive layers, one or more peelable material layers, and the like.
The conductive adhesive of the present invention can usually bond adherends together by applying heat and pressure. The heating temperature is not particularly limited as long as it does not damage the adherend, and is, for example, 70° C. or higher and 250° C. or lower. The pressure is not particularly limited as long as it does not damage the adherend, and is, for example, 0.1 MPa or more and 10 MPa or less. Heating and pressurization are preferably performed, for example, for 0.5 seconds or more and 120 seconds or less.
本発明の導電性接着剤は、被着体同士を電気的に接合させるために用いられる。例えば、互いに異なる材料であって熱膨張係数が異なる被着体同士を接着させるとともに電気的に接続させるための異種の被着体の接着剤として使用することができる。さらに、本発明の導電性接着剤は、異方導電性接着剤、導電性ペースト、導電性接着フィルム等の回路接続材料、アンダーフィル材、LOCテープ等の半導体素子接着材料として使用することができる。 The conductive adhesive of the present invention is used for electrically bonding adherends together. For example, it can be used as an adhesive for different types of adherends for bonding and electrically connecting adherends made of different materials and having different coefficients of thermal expansion. Furthermore, the conductive adhesive of the present invention can be used as an anisotropic conductive adhesive, a conductive paste, a circuit connecting material such as a conductive adhesive film, an underfill material, and a semiconductor element bonding material such as an LOC tape. .
[回路接続材料]
本発明の回路接続材料は、前記導電性樹脂組成物及び/又は前記導電性接着剤を含むものである。本発明の回路接続材料は、必要に応じて、溶媒、チオール系硬化剤以外のエポキシ樹脂を硬化させる硬化剤、密着性付与剤、粘弾性調整剤、湿潤分散剤、硬化促進剤(硬化触媒)、反応性希釈剤、錫粉末以外の導電性粉末、エポキシ樹脂以外の樹脂、酸化防止剤、顔料、充填剤(フィラー)、腐食抑制剤、消泡剤、カップリング剤、沈降防止剤等、レベリング剤、重金属不活性化剤、界面活性剤、pH調整剤、紫外線吸収剤、難燃剤、接着付与剤等からなる群より選ばれる1種以上をさらに含んでいてもよい。
本発明の回路接続材料は、各種電子部品と回路基板との導電接続や電気・電子回路相互の電気的な接続(接着)に用いられる。
回路接続材料の形状等は特に限定されないが、液状又はフィルム状であることが好ましい。
液状の回路接続材料は、例えば、本発明の導電性樹脂組成物に有機溶媒等の溶媒を混合して液状化することで得ることができる。
フィルム状の回路接続材料は、例えば、前記の液状化した本発明の導電性樹脂組成物を剥離性基材上に直接流延・塗布して膜を形成し、乾燥して溶媒を除去してフィルムを形成した後に剥離性基材上から剥がすことで得ることができる。
また、フィルム状の回路接続材料は、例えば、前記の液状化した本発明の導電性樹脂組成物を不織布等に含浸させた後に剥離性基材上に形成し、乾燥して溶媒を除去した後に剥離性基材上から剥がすことで得ることができる。
[Circuit connection material]
The circuit connecting material of the present invention contains the conductive resin composition and/or the conductive adhesive. The circuit-connecting material of the present invention may optionally contain a solvent, a curing agent for curing an epoxy resin other than a thiol-based curing agent, an adhesion imparting agent, a viscoelasticity modifier, a wetting and dispersing agent, and a curing accelerator (curing catalyst). , reactive diluents, conductive powders other than tin powders, resins other than epoxy resins, antioxidants, pigments, fillers, corrosion inhibitors, antifoaming agents, coupling agents, anti-settling agents, etc., leveling agents, heavy metal deactivators, surfactants, pH adjusters, UV absorbers, flame retardants, tackifiers, and the like.
The circuit-connecting material of the present invention is used for conductive connection between various electronic components and circuit boards and for electrical connection (adhesion) between electrical and electronic circuits.
The shape of the circuit-connecting material is not particularly limited, but it is preferably liquid or film-like.
A liquid circuit connecting material can be obtained, for example, by mixing the conductive resin composition of the present invention with a solvent such as an organic solvent to liquefy the mixture.
A film-like circuit-connecting material can be produced, for example, by directly casting and coating the liquefied conductive resin composition of the present invention on a peelable substrate to form a film, and drying to remove the solvent. It can be obtained by peeling off the peelable substrate after forming the film.
Further, the film-like circuit connecting material is formed on a peelable substrate after impregnating a nonwoven fabric or the like with the liquefied conductive resin composition of the present invention, and dried to remove the solvent. It can be obtained by peeling off from the peelable substrate.
回路接続材料を用いた電気的接続方法等は特に限定されない。例えば、電子部品や回路等の電極と、それと相対峙する基材上の電極との間に回路接続材料を設け、加熱して両電極の電気的接続と両電極間の接着を行う方法が挙げられる。加熱の際、必要に応じて加圧することができる。
相対峙する電極との間に回路接続材料を設ける方法は、特に限定されない。例えば、液状の回路接続材料を塗布する方法、フィルム状の回路接続材料を挟む方法等が挙げられる。
また、電子部品等が有するピンと回路との導電接続に際して、ピンの根元に回路接続材料を設け、突合せ接合して導電接続を構成する方法等が挙げられる。
The electrical connection method using the circuit-connecting material is not particularly limited. For example, there is a method in which a circuit connecting material is provided between the electrodes of an electronic component or circuit and the electrodes on the base material facing each other, and the electrodes are electrically connected and the electrodes are bonded together by heating. be done. During heating, pressure can be applied as necessary.
The method of providing the circuit connecting material between the facing electrodes is not particularly limited. Examples thereof include a method of applying a liquid circuit-connecting material and a method of sandwiching a film-like circuit-connecting material.
In addition, when conducting conductive connection between a pin of an electronic component and a circuit, a method of forming a conductive connection by providing a circuit connection material at the base of the pin and butt-joining them can be used.
回路接続材料は、実質的に異方導電性材料として用いることができ、また、接着性に優れた回路接続材料を基材上の相対峙する電極間に形成し、加熱加圧により両電極の接触と基材間の接着を得る電極の接続方法に用いることができる。電極を形成する基材としては、半導体、ガラス、セラミック等の無機質、ポリイミド、ポリカーボネート等の有機物、ガラスエポキシ等のこれらの複合物等の各種組み合わせが適用できる。 The circuit-connecting material can be used substantially as an anisotropically conductive material, and the circuit-connecting material having excellent adhesiveness is formed between the opposing electrodes on the substrate, and the two electrodes are bonded by heating and pressing. It can be used in electrode connection methods to obtain contact and adhesion between substrates. Various combinations of inorganic materials such as semiconductors, glass, and ceramics, organic materials such as polyimides and polycarbonates, and composites thereof such as glass epoxy can be used as the substrate for forming the electrodes.
以下に実施例を挙げて本発明をさらに詳細に説明する。なお、本発明はこれらの実施例に限定されない。特に断りのない限り、「%」は「質量%」を、「部」は「質量部」を意味する。
実施例で用いた成分は、それぞれ以下のとおりである。
The present invention will be described in more detail with reference to examples below. However, the present invention is not limited to these examples. Unless otherwise specified, "%" means "mass %" and "part" means "mass part".
Components used in the examples are as follows.
・錫粉末:球状錫粉末(D50=5.5μm、Sn≧99.5質量%)
・銅粉末:球状銅粉末(粒子径10μm~25μm、Sigma-Aldrich社製、銅powder(spheroidal)、98%)
・エポキシ樹脂1:ビスフェノール型エポキシ樹脂(三菱ケミカル社製、jER828)
・エポキシ樹脂2:ビスフェノール型エポキシ樹脂(三菱ケミカル社製、jER1001)
・エポキシ樹脂3:ビスフェノール型エポキシ樹脂(三菱ケミカル社製、jER1004)
・エポキシ樹脂4:強靭性エポキシ樹脂(日本化薬社製、LCE-2615)
・エポキシ樹脂5:ウレタン変性エポキシ樹脂(ADEKA社製、EPU-73B)
・エポキシ樹脂6:ゴム変性エポキシ樹脂(ADEKA社製、EPR-1415-1)
・エポキシ樹脂7:ポリサルファイド変性エポキシ樹脂(東レファインケミカル社製、FLEP-50)
・有機酸化合物1:グルタル酸
・有機酸化合物2:液状ポリカルボン酸(岡村製油社製、MMA-10R)
・チオール系硬化剤1:多官能チオール化合物(SC有機化学社製、TMMP-LV)
・チオール系硬化剤2:多官能チオール化合物(SC有機化学社製、PEMP-LV)
・チオール系硬化剤3:多官能チオール化合物(SC有機化学社製、DPMP)
・チオール系硬化剤4:多官能チオール化合物(SC有機化学社製、TEMPIC)
・チオール系硬化剤5:多官能チオール化合物(東レファインケミカル社製、QE-340M)
・チオール系硬化剤6:多官能チオール化合物(四国化成工業社製、TS-G)
・チオール系硬化剤7:多官能チオール化合物(四国化成工業社製、C3TS-G)
・チオール系硬化剤8:多官能チオール化合物(昭和電工社製、カレンズ MT NR-1)
・チオール系硬化剤9:多官能チオール化合物(東レファインケミカル社製、LP-3)
・チオール系硬化剤10:多官能チオール化合物(東レファインケミカル社製、LP-2)
・チオール系硬化剤11:多官能チオール化合物(東レファインケミカル社製、LP-31)
・チオール系硬化剤12:多官能チオール化合物(東レファインケミカル社製、LP-55)
・酸無水物系硬化剤:ポリ酸ポリ無水物(岡村製油社製、IPU-22AH)
・フェノール系硬化剤:液状フェノール樹脂(明和化成社製、MEH-8005)
・アミン系硬化剤1:(三菱ケミカル社製、ST-11)
・アミン系硬化剤2:(三菱ケミカル社製、ST-14)
・溶媒1:MFDG(ジプロピレングリコールモノメチルエーテル)
・溶媒2:ブチルカルビトール
・溶媒3:エチルカルビトール
・酸化防止剤1:ヒンダードフェノール系化合物(BASF社製、Irganox 1010)
・酸化防止剤2:ヒンダードフェノール系化合物(精工化学社製、ノンフレックス EBP)
・酸化防止剤3:ヒンダードフェノール系化合物(精工化学社製、ノンフレックス CBP)
・酸化防止剤4:ヒンダードフェノール系化合物(ADEKA社製、アデカスタブ AO-50)
・酸化防止剤5:ヒンダードフェノール系化合物(ADEKA社製、アデカスタブ AO-80)
・酸化防止剤6:ハイドロキノン
・重金属不活性化剤1:ADEKA社製、アデカスタブ CDA-6S
・重金属不活性化剤2:ADEKA社製、アデカスタブ ZS-90
・重金属不活性化剤3:ADEKA社製、アデカスタブ ZS-27
・硬化促進剤1:グアニジン系化合物(三新化学工業社製、サンセラー D)
・硬化促進剤2:グアニジン系化合物(三新化学工業社製、サンセラー DT)
- Tin powder: spherical tin powder (D50 = 5.5 µm, Sn ≥ 99.5% by mass)
・ Copper powder: spherical copper powder (particle size 10 μm to 25 μm, manufactured by Sigma-Aldrich, copper powder (spheroidal), 98%)
・ Epoxy resin 1: bisphenol type epoxy resin (manufactured by Mitsubishi Chemical Corporation, jER828)
・ Epoxy resin 2: bisphenol type epoxy resin (manufactured by Mitsubishi Chemical Corporation, jER1001)
・ Epoxy resin 3: bisphenol type epoxy resin (manufactured by Mitsubishi Chemical Corporation, jER1004)
・ Epoxy resin 4: tough epoxy resin (manufactured by Nippon Kayaku, LCE-2615)
・ Epoxy resin 5: urethane-modified epoxy resin (manufactured by ADEKA, EPU-73B)
・ Epoxy resin 6: rubber-modified epoxy resin (manufactured by ADEKA, EPR-1415-1)
・ Epoxy resin 7: Polysulfide-modified epoxy resin (FLEP-50, manufactured by Toray Fine Chemicals Co., Ltd.)
・Organic acid compound 1: glutaric acid ・Organic acid compound 2: liquid polycarboxylic acid (manufactured by Okamura Oil Co., Ltd., MMA-10R)
・ Thiol-based curing agent 1: polyfunctional thiol compound (manufactured by SC Organic Chemical Co., Ltd., TMMP-LV)
・ Thiol-based curing agent 2: polyfunctional thiol compound (manufactured by SC Organic Chemical Co., Ltd., PEMP-LV)
・ Thiol-based curing agent 3: polyfunctional thiol compound (manufactured by SC Organic Chemical Co., Ltd., DPMP)
- Thiol-based curing agent 4: polyfunctional thiol compound (manufactured by SC Organic Chemical Co., Ltd., TEMPIC)
・ Thiol-based curing agent 5: polyfunctional thiol compound (manufactured by Toray Fine Chemicals Co., Ltd., QE-340M)
・ Thiol-based curing agent 6: polyfunctional thiol compound (manufactured by Shikoku Kasei Kogyo Co., Ltd., TS-G)
· Thiol-based curing agent 7: polyfunctional thiol compound (manufactured by Shikoku Kasei Co., Ltd., C3TS-G)
・ Thiol-based curing agent 8: polyfunctional thiol compound (manufactured by Showa Denko Co., Ltd., Karenz MT NR-1)
・ Thiol-based curing agent 9: polyfunctional thiol compound (manufactured by Toray Fine Chemicals, LP-3)
· Thiol-based curing agent 10: polyfunctional thiol compound (manufactured by Toray Fine Chemicals, LP-2)
· Thiol-based curing agent 11: polyfunctional thiol compound (manufactured by Toray Fine Chemicals, LP-31)
· Thiol-based curing agent 12: polyfunctional thiol compound (manufactured by Toray Fine Chemicals, LP-55)
・ Acid anhydride-based curing agent: polyacid polyanhydride (manufactured by Okamura Oil Co., Ltd., IPU-22AH)
・ Phenolic curing agent: liquid phenolic resin (manufactured by Meiwa Kasei Co., Ltd., MEH-8005)
- Amine-based curing agent 1: (Mitsubishi Chemical Co., Ltd., ST-11)
Amine-based curing agent 2: (Mitsubishi Chemical Co., Ltd., ST-14)
- Solvent 1: MFDG (dipropylene glycol monomethyl ether)
Solvent 2: butyl carbitol Solvent 3: ethyl carbitol Antioxidant 1: Hindered phenolic compound (manufactured by BASF, Irganox 1010)
・ Antioxidant 2: Hindered phenolic compound (manufactured by Seiko Chemical Co., Ltd., Nonflex EBP)
・ Antioxidant 3: Hindered phenolic compound (manufactured by Seiko Chemical Co., Ltd., Nonflex CBP)
· Antioxidant 4: Hindered phenolic compound (ADEKA Co., Adekastab AO-50)
· Antioxidant 5: Hindered phenolic compound (ADEKA Co., Adekastab AO-80)
・ Antioxidant 6: Hydroquinone ・ Heavy metal deactivator 1: ADEKA Co., Ltd., Adekastab CDA-6S
・Heavy metal deactivator 2: ADEKA Co., Ltd., Adekastab ZS-90
・Heavy metal deactivator 3: ADEKA Co., Ltd., Adekastab ZS-27
・ Curing accelerator 1: Guanidine compound (Sanshin Chemical Industry Co., Ltd., Suncellar D)
・ Curing accelerator 2: Guanidine-based compound (Sanshin Chemical Industry Co., Ltd., Sancellar DT)
導電性樹脂組成物のペースト状態及び硬化性、導電性樹脂組成物により形成された導電膜(乾燥塗膜)の接合強度、表面絶縁性、体積抵抗率及びLED点灯試験の測定・評価は、以下に示す方法で行った。
<ペースト状態>
導電性樹脂組成物の構成成分及びその含有量(部)を、それぞれ表1に示すものとし、自転・公転ミキサー(シンキー社製、「あわとり練太郎 AR-100」)を用いて混合、撹拌して導電性樹脂組成物を得た。この導電性樹脂組成物の外観を目視で観察し、以下の基準で評価した。本発明において、Aは合格、Cは不合格である。
A:導電性樹脂組成物は、均一であった。
C:ダマ等が発生しており、導電性樹脂組成物は不均一であった。
Paste state and curability of the conductive resin composition, bonding strength of the conductive film (dry coating film) formed from the conductive resin composition, surface insulation, volume resistivity, and measurement and evaluation of the LED lighting test are as follows. was performed by the method shown in .
<Paste state>
The components of the conductive resin composition and their content (parts) are shown in Table 1, respectively, and mixed and stirred using a rotation / revolution mixer (manufactured by Thinky Co., Ltd., "Awatori Mixer AR-100"). Then, a conductive resin composition was obtained. The appearance of this conductive resin composition was visually observed and evaluated according to the following criteria. In the present invention, A is pass and C is fail.
A: The conductive resin composition was uniform.
C: Lumps and the like were generated, and the conductive resin composition was non-uniform.
<硬化性>
2cm×2cmの穴を開けたPETフィルムをマスクとして、導電性樹脂組成物を手刷り印刷し、ガラス基材上に2cm×2cmの塗膜を作製した後に、160℃・60分の熱処理条件で加熱硬化した。得られた塗膜の中央をヘラで軽く触れたときに、塗膜が変形する度合いを、以下の基準で評価した。本発明において、Aは合格、Cは不合格である。
A:塗膜が硬化しており、変形しなかった。
C:塗膜が硬化しておらず、容易に変形した。
<Curability>
Using a PET film with a hole of 2 cm × 2 cm as a mask, the conductive resin composition was hand-printed to form a coating film of 2 cm × 2 cm on the glass substrate, and then under heat treatment conditions of 160 ° C. for 60 minutes. Heat cured. When the center of the resulting coating film was lightly touched with a spatula, the degree of deformation of the coating film was evaluated according to the following criteria. In the present invention, A is pass and C is fail.
A: The coating film was cured and was not deformed.
C: The coating film was not cured and easily deformed.
<接合強度>
面積2.0mm2の銅が4mm間隔でエッチングされたガラスエポキシ基板(陽銘社製)と5025チップ抵抗(ローム社製、MCR-50)を準備した。前記チップ抵抗の各電極端子それぞれの下に導電性樹脂組成物を面積1.5mm2、厚さ100μmとなるように塗布し、ガラスエポキシ基板上の銅パターン配線と接合し、160℃・60分の熱処理条件で導電性樹脂組成物を硬化して測定用サンプルを作製した。
得られたサンプルについて、Bonding Tester PTR1102(レスカ社製)を用いてダイシェアテスト(0.1mm/sec)を実施し、接合強度を測定した。
<Joint strength>
A glass epoxy substrate (manufactured by Yomei Co., Ltd.) having an area of 2.0 mm 2 and copper etched at intervals of 4 mm and a 5025 chip resistor (manufactured by Rohm Co., MCR-50) were prepared. Under each electrode terminal of the chip resistor, a conductive resin composition was applied so as to have an area of 1.5 mm 2 and a thickness of 100 μm, and was bonded to a copper pattern wiring on a glass epoxy substrate, and was heated at 160° C. for 60 minutes. A measurement sample was prepared by curing the conductive resin composition under the heat treatment conditions of .
The resulting sample was subjected to a die shear test (0.1 mm/sec) using a Bonding Tester PTR1102 (manufactured by Lesca) to measure the bonding strength.
<表面絶縁性>
2cm×2cmの穴を開けたPETフィルムをマスクとして、導電性樹脂組成物を手刷り印刷し、プラスチックフィルム基材上に2cm×2cmの塗膜を作製した。次いで、160℃・60分の熱処理条件で加熱硬化し、熱処理後の膜厚が100μm又は表5に記載されたものである導電膜(乾燥塗膜)を作製した。導電膜(乾燥塗膜)の体積抵抗率を、抵抗率計「ロレスタGP-MCP T610」(日東精工アナリテック社製)により測定し、以下の基準で評価した。
A:表面絶縁(体積抵抗率が1.0×10-1Ω・cm以上)
C:表面導電(体積抵抗率が1.0×10-1Ω・cm未満)
<Surface insulation>
Using a PET film with holes of 2 cm×2 cm as a mask, the conductive resin composition was hand-printed to prepare a coating film of 2 cm×2 cm on a plastic film substrate. Then, it was heat-cured under heat treatment conditions of 160° C. for 60 minutes to prepare a conductive film (dry coating film) having a film thickness of 100 μm after heat treatment or one described in Table 5. The volume resistivity of the conductive film (dried coating film) was measured with a resistivity meter “Loresta GP-MCP T610” (manufactured by Nitto Seiko Analytic Tech) and evaluated according to the following criteria.
A: Surface insulation (volume resistivity of 1.0 × 10 -1 Ω cm or more)
C: Surface conductivity (volume resistivity less than 1.0×10 −1 Ω·cm)
<LED点灯試験>
エッチングにより面積6.9mm2の銅が3.8mm間隔で形成されているガラスエポキシ基板と5025LEDチップを準備した。前記LEDチップの各電極端子それぞれの下に導電性樹脂組成物を面積2.5mm2となるように塗布した後に、前記ガラスエポキシ基板上の銅パターン配線と接合し、160℃・60分の熱処理条件で導電性樹脂組成物を硬化して測定用サンプルを作製した。
LEDチェッカーを用い、起電力3Vの電圧を配線の両端に印加し、以下の基準で評価した。本発明において、Aが合格、Cが不合格である。
A:LEDが点灯する。
C:LEDが点灯しない。
<LED lighting test>
A glass-epoxy substrate and a 5025 LED chip were prepared by etching copper having an area of 6.9 mm 2 at intervals of 3.8 mm. After applying a conductive resin composition under each electrode terminal of the LED chip so that the area is 2.5 mm 2 , it is joined to the copper pattern wiring on the glass epoxy substrate and heat treated at 160 ° C. for 60 minutes. A measurement sample was prepared by curing the conductive resin composition under the conditions.
Using an LED checker, a voltage with an electromotive force of 3 V was applied to both ends of the wiring, and evaluation was made according to the following criteria. In the present invention, A is a pass and C is a fail.
A: The LED lights up.
C: LED does not light up.
<体積抵抗率>
2cm×2cmの穴を開けたPETフィルムをマスクとして、導電性樹脂組成物を手刷り印刷し、プラスチックフィルム基材上に2cm×2cmの塗膜を作製した。次いで、160℃・60分の熱処理条件で加熱硬化し、熱処理(焼成)後の膜厚(乾燥塗膜の膜厚)が表6に記載されたものである導電膜(乾燥塗膜)を作製した。導電膜(乾燥塗膜)の体積抵抗率を、抵抗率計「ロレスタGP-MCP T610」(日東精工アナリテック社製)により測定した。
<Volume resistivity>
Using a PET film with holes of 2 cm×2 cm as a mask, the conductive resin composition was hand-printed to prepare a coating film of 2 cm×2 cm on a plastic film substrate. Next, heat curing is performed under heat treatment conditions of 160 ° C. for 60 minutes, and a conductive film (dry coating film) having a film thickness (thickness of dry coating film) after heat treatment (baking) as shown in Table 6 is produced. bottom. The volume resistivity of the conductive film (dried coating film) was measured with a resistivity meter “Loresta GP-MCP T610” (manufactured by Nitto Seiko Analytic Tech).
[実施例1]
15.00部の錫粉末、0.48部のエポキシ樹脂1、0.40部の有機酸化合物1、0.36部のチオール系硬化剤1及び1.00部の溶媒1を混合し、自転・公転ミキサー(シンキー社製、「あわとり練太郎 AR-100」)を用い混合、撹拌して導電性樹脂組成物を得た。
2cm×2cmの穴を開けたPETフィルムをマスクとして、得られた導電性樹脂組成物を手刷り印刷し、ガラス基材上に2cm×2cmの塗膜を作製した。次いで、160℃・60分の熱処理条件で加熱硬化し、熱処理後の膜厚が100μmである導電膜(乾燥塗膜)を作製した。
得られた導電性樹脂組成物について、ペースト状態及び硬化性を評価した。
得られた導電性樹脂組成物を用いて、LED点灯試験及び接合強度の測定を行った。
得られた導電膜(乾燥塗膜)について、表面絶縁性の測定を行った。
これらの結果を、表1に併せて示す。
[Example 1]
15.00 parts of tin powder, 0.48 parts of epoxy resin 1, 0.40 parts of organic acid compound 1, 0.36 parts of thiol-based curing agent 1 and 1.00 parts of solvent 1 are mixed,・Mixed and stirred using a revolution mixer (manufactured by THINKY Co., Ltd., "Awatori Mixer AR-100") to obtain a conductive resin composition.
Using a PET film with holes of 2 cm×2 cm as a mask, the resulting conductive resin composition was hand-printed to prepare a coating film of 2 cm×2 cm on a glass substrate. Then, it was heat-cured under heat treatment conditions of 160° C. for 60 minutes to prepare a conductive film (dry coating film) having a film thickness of 100 μm after the heat treatment.
The resulting conductive resin composition was evaluated for paste state and curability.
An LED lighting test and bonding strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dried coating film) were measured.
These results are also shown in Table 1.
[実施例2~22、比較例1~4]
導電性樹脂組成物の構成成分及びその含有量(部)を、それぞれ表1~表3に示すものとしたほかは、実施例1と同様にして導電性樹脂組成物及び導電膜(乾燥塗膜)を作製した。
得られた導電性樹脂組成物について、ペースト状態及び硬化性を評価した。
得られた導電性樹脂組成物を用いて、LED点灯試験及び接合強度の測定を行った。
得られた導電膜(乾燥塗膜)について、表面絶縁性の測定を行った。
これらの結果を、表1~表3に併せて示す。
比較例1は、ペースト状態はAであったが、硬化性評価がCで導電膜(乾燥塗膜)を形成することができなかったため、接合強度、表面絶縁性及びLED点灯試験の評価・測定を行うことができなかった。比較例2、3は、ペースト状態がCであり、導電性樹脂組成物が不均一であるため、硬化性、接合強度、表面絶縁性及びLED点灯試験の評価・測定を行うことができなかった。
[Examples 2 to 22, Comparative Examples 1 to 4]
The conductive resin composition and the conductive film (dried coating film) were prepared in the same manner as in Example 1, except that the constituent components of the conductive resin composition and their contents (parts) were as shown in Tables 1 to 3, respectively. ) was made.
The resulting conductive resin composition was evaluated for paste state and curability.
An LED lighting test and bonding strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dried coating film) were measured.
These results are also shown in Tables 1 to 3.
In Comparative Example 1, the paste state was A, but the curability evaluation was C and a conductive film (dry coating film) could not be formed, so evaluation and measurement of bonding strength, surface insulation, and LED lighting test could not do In Comparative Examples 2 and 3, the paste state was C, and the conductive resin composition was non-uniform. Therefore, evaluation and measurement of curability, bonding strength, surface insulation, and LED lighting test could not be performed. .
[実施例23]
2.00部のエポキシ樹脂1、1.82部の有機酸化合物1、0.91部のチオール系硬化剤1、0.91部のフェノール系硬化剤及び4.55部の溶媒3を混合して、ワニスV-1を得た。
2.24部のワニスV-1及び15.00部の錫粉末を混合し、自転・公転ミキサー(シンキー社製、「あわとり練太郎 AR-100」)を用い混合、撹拌して導電性樹脂組成物を作製した。
得られた導電性樹脂組成物を用い、実施例1と同様にして、熱処理後の膜厚が表5に記載されたものである導電膜(乾燥塗膜)を作製した。
得られた導電性樹脂組成物を用いて、LED点灯試験及び接合強度の測定を行った。
得られた導電膜(乾燥塗膜)について、表面絶縁性の測定を行った。
これらの結果を、表5に併せて示す。
[Example 23]
2.00 parts of epoxy resin 1, 1.82 parts of organic acid compound 1, 0.91 parts of thiol curing agent 1, 0.91 parts of phenolic curing agent and 4.55 parts of solvent 3 were mixed. to obtain varnish V-1.
2.24 parts of varnish V-1 and 15.00 parts of tin powder are mixed, mixed and stirred using a rotation/revolution mixer (manufactured by Thinky Co., Ltd., "Awatori Mixer AR-100") to form a conductive resin. A composition was made.
Using the obtained conductive resin composition, in the same manner as in Example 1, a conductive film (dry coating film) having a thickness shown in Table 5 after heat treatment was produced.
An LED lighting test and a bonding strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dried coating film) were measured.
These results are also shown in Table 5.
[実施例24~33]
ワニスV-1~V-10の構成成分及びその含有量(部)を表4に示すものとし、導電性樹脂組成物の構成成分及びその含有量(部)を表5に示すものとしたほかは、実施例23と同様にして導電性樹脂組成物及び熱処理後の膜厚が表5に記載されたものである導電膜(乾燥塗膜)を作製した。
得られた導電性樹脂組成物を用いて、LED点灯試験及び接合強度の測定を行った。
得られた導電膜(乾燥塗膜)について、表面絶縁性の測定を行った。
これらの結果を、表5に併せて示す。
[Examples 24-33]
The constituent components of the varnishes V-1 to V-10 and their contents (parts) are shown in Table 4, and the constituent components and their contents (parts) of the conductive resin composition are shown in Table 5. In the same manner as in Example 23, a conductive film (dry coating film) having the thickness shown in Table 5 after the conductive resin composition and the heat treatment was produced.
An LED lighting test and bonding strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dried coating film) were measured.
These results are also shown in Table 5.
[実施例34~37]
ワニスV-8、V-10及びV-12の構成成分及びその含有量(部)を表4に示すものとし、導電性樹脂組成物の構成成分及びその含有量(部)を表6に示すものとしたほかは、実施例23と同様にして導電性樹脂組成物及び熱処理後の膜厚が表6に記載されたものである導電膜(乾燥塗膜)を作製した。
得られた導電性樹脂組成物を用いて、接合強度の測定を行った。
得られた導電膜(乾燥塗膜)について、体積抵抗率の測定を行った。
これらの結果を、表6に併せて示す。
[Examples 34-37]
The constituent components and their contents (parts) of the varnishes V-8, V-10 and V-12 are shown in Table 4, and the constituent components and their contents (parts) of the conductive resin composition are shown in Table 6. A conductive film (dry coating film) having the conductive resin composition and the film thickness after heat treatment as described in Table 6 was prepared in the same manner as in Example 23 except that it was used.
The bonding strength was measured using the obtained conductive resin composition.
The volume resistivity of the obtained conductive film (dried coating film) was measured.
These results are also shown in Table 6.
[実施例38~49]
ワニスV-11の構成成分及びその含有量(部)を表4に示すものとし、導電性樹脂組成物の構成成分及びその含有量(部)を表7に示すものとし、熱処理後の膜厚を100μmとしたほかは、実施例23と同様にして導電性樹脂組成物及び導電膜(乾燥塗膜)を作製した。
得られた導電性樹脂組成物を用いて、LED点灯試験及び接合強度の測定を行った。
得られた導電膜(乾燥塗膜)について、表面絶縁性の測定を行った。
これらの結果を、表7に併せて示す。
[Examples 38-49]
The constituent components of the varnish V-11 and their content (parts) are shown in Table 4, the constituent components of the conductive resin composition and their content (parts) are shown in Table 7, and the film thickness after heat treatment A conductive resin composition and a conductive film (dry coating film) were produced in the same manner as in Example 23, except that the thickness was 100 μm.
An LED lighting test and bonding strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dried coating film) were measured.
These results are also shown in Table 7.
実施例1~33、38~49に係る導電性樹脂組成物により形成された導電膜(乾燥塗膜)は、いずれも体積抵抗率が1.0×10-1Ω・cm以上であり、表面絶縁性がA評価でありながらLED点灯試験に合格する特異な特性を示している。これより、本発明の導電性樹脂組成物は、膜を形成した際に、表面が実質的に絶縁体となっているにもかかわらず、内部が導電性を示す特性を有する場合があることがわかる。そして、本発明の導電性樹脂組成物を用いて導電接続を形成した場合、接続部材間に導電接続を形成しつつ、膜表面を実質的に絶縁性とすることが可能であることから、導電性インク、導電性接着剤及び回路接続材料等の導電性材料として有用であることが分かる。
実施例34~37に係る導電性樹脂組成物により形成された導電膜(乾燥塗膜)は、いずれも体積抵抗率が1.2×10-4Ω・cm以下(実施例34~36では、10-5Ω・cmオーダー)という、銀ペーストと同等以上の導電性を示し、導電性に優れたものであった。これより、銀ペースト等と比較して低コストであり、銀ペーストと同等の高い導電性を示す導電性樹脂組成物が形成されたことが分かる。
さらに、表1~表3、表5~表7に示される通り、本発明の導電性樹脂組成物により形成される導電膜(乾燥塗膜)は、その接合強度が強力であり、基材に対する密着性が高いことがわかる。特に、有機酸化合物を2種併用した実施例28~30、32~36、38~49では、接合強度が大きくなっている。
The conductive films (dried coating films) formed from the conductive resin compositions according to Examples 1 to 33 and 38 to 49 all have a volume resistivity of 1.0 × 10 -1 Ω cm or more, and a surface It has a unique characteristic of passing the LED lighting test even though the insulation is rated A. From this, it can be seen that the conductive resin composition of the present invention, when formed into a film, may have a characteristic that the interior exhibits conductivity even though the surface is substantially an insulator. Recognize. When a conductive connection is formed using the conductive resin composition of the present invention, the film surface can be made substantially insulating while forming a conductive connection between connection members. It is found useful as conductive materials such as conductive inks, conductive adhesives and circuit connecting materials.
The conductive films (dried coating films) formed from the conductive resin compositions according to Examples 34 to 37 all had a volume resistivity of 1.2×10 −4 Ω cm or less (in Examples 34 to 36, 10 −5 Ω·cm order), which is equal to or higher than that of the silver paste, and was excellent in conductivity. From this, it can be seen that a conductive resin composition was formed which is less expensive than silver paste or the like and exhibits high conductivity equivalent to that of silver paste.
Furthermore, as shown in Tables 1 to 3 and Tables 5 to 7, the conductive film (dry coating film) formed by the conductive resin composition of the present invention has a strong bonding strength, and It can be seen that the adhesion is high. In particular, in Examples 28-30, 32-36, and 38-49 in which two types of organic acid compounds were used in combination, the bonding strength was high.
一方、有機酸化合物を含まない比較例1に係る導電性樹脂組成物は、硬化性評価がCで導電膜(乾燥塗膜)を形成することができないものであり、チオール系硬化剤に替えてアミン系硬化剤を用いた比較例2、3に係る導電性樹脂組成物は、ペースト状態がCでダマが発生し均一な導電性樹脂組成物を作製できないものであり、錫粉末に替えて銅粉末を用いた比較例4に係る導電性樹脂組成物は、LED点灯試験評価がCで十分な導電性を示さないものであった。 On the other hand, the conductive resin composition according to Comparative Example 1, which does not contain an organic acid compound, has a curability evaluation of C and cannot form a conductive film (dried coating film). The conductive resin compositions according to Comparative Examples 2 and 3 using an amine-based curing agent were in a paste state of C and lumps occurred, making it impossible to prepare a uniform conductive resin composition. The conductive resin composition according to Comparative Example 4 using the powder was evaluated as C in the LED lighting test and did not exhibit sufficient conductivity.
Claims (6)
を含む、導電性樹脂組成物。 (a) tin powder, (b) epoxy resin, (c) organic acid compound and (d) thiol-based curing agent,
A conductive resin composition comprising:
(i)25℃で液状である、及び/又は、
(ii)ビスフェノール型エポキシ樹脂、ゴム変性エポキシ樹脂、脂環式エポキシ樹脂、グリシジルアミン型エポキシ樹脂、ウレタン変性エポキシ樹脂、ポリサルファイド変性エポキシ樹脂、キレート変性エポキシ樹脂、トリスフェノールメタン型エポキシ樹脂、ナフタレン型エポキシ樹脂、ジシクロペンタジエン変性エポキシ樹脂、脂肪族エポキシ樹脂、ポリエーテル変性エポキシ樹脂、多官能芳香族エポキシ樹脂及び水素添加ビスフェノール型エポキシ樹脂からなる群より選ばれる少なくとも1種である、請求項1に記載の導電性樹脂組成物。 (b) epoxy resin
(i) liquid at 25° C. and/or
(ii) bisphenol-type epoxy resin, rubber-modified epoxy resin, alicyclic epoxy resin, glycidylamine-type epoxy resin, urethane-modified epoxy resin, polysulfide-modified epoxy resin, chelate-modified epoxy resin, trisphenolmethane-type epoxy resin, naphthalene-type epoxy 2. The resin according to claim 1, which is at least one selected from the group consisting of resins, dicyclopentadiene-modified epoxy resins, aliphatic epoxy resins, polyether-modified epoxy resins, polyfunctional aromatic epoxy resins, and hydrogenated bisphenol-type epoxy resins. The conductive resin composition of.
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