CN118119662A - Conductive resin composition - Google Patents
Conductive resin composition Download PDFInfo
- Publication number
- CN118119662A CN118119662A CN202280070457.2A CN202280070457A CN118119662A CN 118119662 A CN118119662 A CN 118119662A CN 202280070457 A CN202280070457 A CN 202280070457A CN 118119662 A CN118119662 A CN 118119662A
- Authority
- CN
- China
- Prior art keywords
- conductive
- resin composition
- epoxy resin
- conductive resin
- curing agent
- 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 356
- 239000003822 epoxy resin Substances 0.000 claims abstract description 250
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 250
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 208
- -1 organic acid compound Chemical class 0.000 claims abstract description 158
- 230000001070 adhesive effect Effects 0.000 claims abstract description 111
- 239000000853 adhesive Substances 0.000 claims abstract description 110
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 79
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 58
- 150000003573 thiols Chemical class 0.000 claims abstract description 55
- 239000000463 material Substances 0.000 claims abstract description 47
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 29
- 239000000126 substance Substances 0.000 claims description 35
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 28
- 229930185605 Bisphenol Natural products 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 16
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 12
- 229920001971 elastomer Polymers 0.000 claims description 10
- 239000005060 rubber Substances 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 229920001021 polysulfide Polymers 0.000 claims description 9
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 claims description 8
- 229920002732 Polyanhydride Polymers 0.000 claims description 8
- 239000005077 polysulfide Substances 0.000 claims description 8
- 150000008117 polysulfides Polymers 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000004844 aliphatic epoxy resin Substances 0.000 claims description 6
- 239000013522 chelant Substances 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 239000000758 substrate Substances 0.000 abstract description 88
- 238000000576 coating method Methods 0.000 description 156
- 239000011248 coating agent Substances 0.000 description 154
- 239000002904 solvent Substances 0.000 description 61
- 238000012360 testing method Methods 0.000 description 54
- 238000010438 heat treatment Methods 0.000 description 44
- 239000011521 glass Substances 0.000 description 43
- 238000005259 measurement Methods 0.000 description 39
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 35
- 229920005989 resin Polymers 0.000 description 35
- 239000011347 resin Substances 0.000 description 35
- 238000000034 method Methods 0.000 description 34
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 32
- 238000009413 insulation Methods 0.000 description 32
- 230000000052 comparative effect Effects 0.000 description 30
- 239000000470 constituent Substances 0.000 description 28
- 239000000843 powder Substances 0.000 description 28
- 239000004593 Epoxy Substances 0.000 description 27
- 239000003963 antioxidant agent Substances 0.000 description 27
- 235000006708 antioxidants Nutrition 0.000 description 27
- 239000000976 ink Substances 0.000 description 26
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 24
- 229910052709 silver Inorganic materials 0.000 description 24
- 239000004332 silver Substances 0.000 description 24
- 239000002966 varnish Substances 0.000 description 22
- 125000003700 epoxy group Chemical group 0.000 description 21
- 229920002799 BoPET Polymers 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 18
- 229910052802 copper Inorganic materials 0.000 description 16
- 239000010949 copper Substances 0.000 description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 15
- 230000003078 antioxidant effect Effects 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- 238000011156 evaluation Methods 0.000 description 14
- 239000005011 phenolic resin Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000945 filler Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 11
- 239000002270 dispersing agent Substances 0.000 description 10
- 238000007639 printing Methods 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 229910001385 heavy metal Inorganic materials 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- 238000009736 wetting Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 239000003607 modifier Substances 0.000 description 8
- 238000007650 screen-printing Methods 0.000 description 8
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 239000004020 conductor Substances 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere 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
- 230000007797 corrosion Effects 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 229910000679 solder Inorganic materials 0.000 description 6
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 5
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 5
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 5
- 230000001747 exhibiting effect Effects 0.000 description 5
- 239000012212 insulator Substances 0.000 description 5
- 239000006078 metal deactivator Substances 0.000 description 5
- 239000003002 pH adjusting agent Substances 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 4
- LYWVNPSVLAFTFX-UHFFFAOYSA-N 4-methylbenzenesulfonate;morpholin-4-ium Chemical compound C1COCCN1.CC1=CC=C(S(O)(=O)=O)C=C1 LYWVNPSVLAFTFX-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 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 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000005266 casting Methods 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
- 150000002118 epoxides Chemical class 0.000 description 4
- 238000005530 etching Methods 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- 238000000518 rheometry Methods 0.000 description 4
- 102220043159 rs587780996 Human genes 0.000 description 4
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- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 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
- 239000006097 ultraviolet radiation absorber Substances 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
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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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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- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
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- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
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- 229960002969 oleic acid Drugs 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- YOURXVGYNVXQKT-UHFFFAOYSA-N oxacycloundecane-2,11-dione Chemical compound O=C1CCCCCCCCC(=O)O1 YOURXVGYNVXQKT-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- PFPYHYZFFJJQFD-UHFFFAOYSA-N oxalic anhydride Chemical compound O=C1OC1=O PFPYHYZFFJJQFD-UHFFFAOYSA-N 0.000 description 1
- LJAGLQVRUZWQGK-UHFFFAOYSA-N oxecane-2,10-dione Chemical compound O=C1CCCCCCCC(=O)O1 LJAGLQVRUZWQGK-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007649 pad printing Methods 0.000 description 1
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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
- 239000006072 paste Substances 0.000 description 1
- TWBKZBJAVASNII-UHFFFAOYSA-N pentadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCS(O)(=O)=O TWBKZBJAVASNII-UHFFFAOYSA-N 0.000 description 1
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- 239000013034 phenoxy resin Substances 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
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- 150000004714 phosphonium salts Chemical class 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
- 239000001739 pinus spp. 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
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- 229920002451 polyvinyl alcohol 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
- 230000008569 process Effects 0.000 description 1
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- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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
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- 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
- 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
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 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
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 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
- 239000001384 succinic acid Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
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- 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
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 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
- 239000010936 titanium Substances 0.000 description 1
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- 150000003624 transition metals Chemical class 0.000 description 1
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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- 235000019165 vitamin E Nutrition 0.000 description 1
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- 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
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Landscapes
- Conductive Materials (AREA)
Abstract
The present invention provides a conductive resin composition which exhibits excellent conductivity and adhesion (adhesive strength) to various substrates, and is useful as a conductive ink, a conductive adhesive, a circuit connecting material, etc., and further provides 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 a circuit connecting material containing the conductive resin composition. As a solution, there is provided a conductive resin composition which contains (a) tin powder, (B) an epoxy resin and (c) an organic acid compound and satisfies the following requirements (A) and/or (B); (A): the content of (a) tin powder in the total amount of (a) tin powder, (B) epoxy resin and (c) organic acid compound of 100 mass% is 90.1 mass% or more, (B): contains (d) a curing agent, wherein (d) the curing agent contains (d 1) an acid anhydride curing agent, (d 2) a thiol curing agent and (d 3) at least 1 phenolic curing agent.
Description
Technical Field
The present invention relates to a conductive resin composition. The present invention also relates to a conductive film, a conductive ink used for forming a circuit such as screen printing on a substrate, a conductive adhesive for bonding a portion to be bonded to have conductivity, and a circuit connecting material used for electrically connecting an electronic component to a circuit board or the like.
Background
As conductive resin compositions, various compositions are known, and as conductive pastes, conductive films, conductive inks, conductive paints, circuit connecting materials, conductive adhesives, and the like, they are used for various applications such as formation of electronic circuits and adhesion of electronic components.
For example, a film having conductivity is desired, and is useful for forming a conductive structure such as a conductive circuit or an electrode.
For example, a conductive ink is desired which is applicable to various printing methods and is useful for producing flexible plastic substrates, film substrates, sheet substrates, resin molded articles, glass, epoxy glass, ceramic substrates, and the like having conductive structures such as interconnections, wires, electrodes, and the like.
For example, a circuit connecting material for mounting various electronic components such as LED elements, semiconductor elements, and capacitors on the same circuit board at high density and for achieving high integration in electronic devices such as computers and mobile phones is demanded.
Heretofore, as a conductive resin composition, a conductive resin composition (conductive paste) containing a resin and conductive particles has been known. However, since the volume resistivity of the conductive resin composition cannot be sufficiently reduced, silver particles are required to be used as the conductive particles when the conductive resin composition is used for applications requiring low volume resistivity. In addition, when a large amount of conductive particles are contained in order to reduce the volume resistivity of the film obtained from the conductive resin composition, the adhesion (adhesive strength) of the film to various substrates is lowered, which is not satisfactory.
Patent document 1 discloses a conductive paste composition characterized in that 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 the conductive paste composition further contains an ester compound having a specific molecular weight and structure, or a salt thereof, or an ether/amine compound.
Patent literature
Patent document 1: japanese patent laid-open No. 2020-205245
Disclosure of Invention
However, silver particles are very expensive, and therefore are disadvantageous in terms of cost, and on the other hand, when conductive particles other than silver particles are used, the volume resistivity of the film of the conductive resin composition may be increased, and the conductivity may become insufficient. In addition, when a large amount of conductive particles are used to reduce the volume resistivity, the adhesion to various substrates may be insufficient.
Heretofore, a conductive resin composition having low volume resistivity and excellent adhesion (adhesive strength) to various substrates when forming a conductive film has not been known.
The present invention aims to provide a conductive resin composition which exhibits excellent conductivity and excellent adhesion (adhesive strength) to various substrates, and is useful as a conductive ink, a conductive adhesive, a circuit connecting material, and the like. Further provided are 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 a circuit connecting material containing the conductive resin composition.
The present inventors have conducted intensive studies to solve the above problems, and as a result, have found that the above problems can be solved by preparing a conductive resin composition having a specific composition, and have completed the present invention.
Specifically, as shown below.
The conductive resin composition according to item 1, which is characterized by comprising (a) tin powder, (B) an epoxy resin and (c) an organic acid compound, and satisfying the following requirements (A) and/or (B):
(A) : the content of the tin powder (a) in the total amount of 100 mass% of the tin powder (a), the epoxy resin (b) and the organic acid compound (c) is 90.1 mass% or more,
(B) : the resin composition contains (d) a curing agent, wherein the (d) curing agent contains (d 1) an acid anhydride curing agent, (d 2) a thiol curing agent and (d 3) at least 1 phenolic curing agent.
The electroconductive resin composition according to item 1, wherein the (b) epoxy resin satisfies the following requirements (i) and/or (ii):
(i) : is in a liquid state at the temperature of 25 ℃,
(Ii) : is at least 1 selected from 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, triphenol methane type epoxy resin, naphthalene type epoxy resin, dicyclopentadiene modified epoxy resin, aliphatic epoxy resin, polyether modified epoxy resin, polyfunctional aromatic epoxy resin and hydrogenated bisphenol type epoxy resin.
The electroconductive resin composition according to item 1 or 2, characterized in that the acid anhydride-based curing agent (d 1) is a polyacid polyanhydride represented by the following structural formula (1);
[ chemical formula 1]
In the structural formula (1), R 1 is a straight-chain or branched-chain hydrocarbon group with a carbon number of 10-40.
The electroconductive resin composition according to item 1 or 2, wherein the (d 1) acid anhydride-based curing agent, the (d 2) thiol-based curing agent, or the (d 3) phenol-based curing agent is in a liquid state at 25 ℃.
Item 5. A conductive film, characterized by being formed of the conductive resin composition described in item 1 or 2, and having a volume resistivity of less than 1.0X -2 Ω·cm.
The electroconductive ink according to item 6, characterized by comprising the electroconductive resin composition according to item 1 or 2.
The conductive adhesive according to item 7, characterized by comprising the conductive resin composition according to item 1 or 2.
The circuit-connecting material according to item 8, which is characterized by comprising the electroconductive resin composition according to item 1 or 2.
According to the present invention, a conductive resin composition exhibiting excellent conductivity and excellent adhesion (adhesive strength) to various substrates, and useful as a conductive ink, a conductive adhesive, a circuit connecting material, and the like, can be provided.
The conductive resin composition of the present invention is useful as a printed electronic material, and is extremely useful for mass production of various electronic devices such as display devices, vehicle-related parts, ioT, and mobile communication systems (Mobile Communication System).
Detailed Description
The 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.
[ Conductive resin composition ]
The conductive resin composition of the present invention is a conductive resin composition, which is characterized by containing (a) tin powder, (B) an epoxy resin and (c) an organic acid compound, and satisfying the following requirements (A) and/or (B);
(A) : the content of the tin powder (a) in the total amount of 100 mass% of the tin powder (a), the epoxy resin (b) and the organic acid compound (c) is 90.1 mass% or more,
(B) : the resin composition contains (d) a curing agent, wherein the (d) curing agent contains (d 1) an acid anhydride curing agent, (d 2) a thiol curing agent and (d 3) at least 1 phenolic curing agent.
(A) tin powder
The tin powder contained in the conductive resin composition of the present invention is a powder composed of 99.5 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 analysis (XRF) apparatus or the like.
The unavoidable impurities contained in the tin powder include, for example, 1 or more other atoms selected from 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, fe and the like.
The content of other atoms in the tin powder is preferably less than 0.3 mass%, more preferably 0.1 mass% or less.
The shape of the tin powder is not particularly limited. For example, a flake-shaped (flake-shaped), flat, spherical, nearly spherical (for example, aspect ratio of 1.5 or less), block-shaped, plate-shaped, polygonal cone-shaped, polyhedral, rod-shaped, fibrous, needle-shaped, irregular-shaped tin powder can be used depending on the application or the like. In the present invention, from the viewpoints of volume resistivity, dispersibility, handleability, and the like, a flake-like, spherical, nearly spherical, flat, irregular-shaped tin powder is preferable.
The volume average particle diameter (50% particle diameter D50 of cumulative frequency% diameter in volume standard particle size distribution) of the spherical or irregularly shaped tin powder is not particularly limited. The D50 is, for example, 0.5 μm or more, preferably 1.0 μm or more, more preferably 3.0 μm or more, 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, dispersibility and handling properties of the tin powder are good. When D50 is 300 μm or less, volume resistivity can be reduced, and dispersibility and handleability are good.
The average diameter, average thickness and aspect ratio (average diameter/average thickness) of the flat or scaly 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, 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, 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, and more preferably 50 or more.
In the conductive resin composition of the present invention, the content of (a) tin powder in the conductive resin composition satisfying the requirements of (a) is 90.1 mass% or more based on 100 mass% of the total amount of (a) tin powder, (b) epoxy resin and (c) organic acid compound. The content is preferably 90.5 mass% or more, more preferably 91 mass% or more, still more preferably 92 mass% or more, for example 98.0 mass% or less, and preferably 97.5 mass% or less.
When the content of the (a) tin powder is less than 90.1 mass% based on 100 mass% of the total amount of the (a) tin powder, the (b) epoxy resin and the (c) organic acid compound, the electrical conductivity may be lowered and the volume resistivity may be increased, or when the LED is not lighted in the LED lighting test described in examples a to D, the adhesive strength of the coating film may be lowered if the content exceeds 98.0 mass%.
In the conductive resin composition of the present invention, the content of the tin powder (a) in the conductive resin composition satisfying the requirements of the above (B) is not particularly limited. The conductive resin composition can be appropriately set from the viewpoint of conductivity and the like of the conductive resin composition. For example, the total amount of the tin powder (a), the epoxy resin (b), the organic acid compound (c) and the curing agent (d) is 50.0 mass% or more, preferably 60.0 mass% or more, more preferably 85.0 mass% or more, still more preferably 88.0 mass% or more, still more preferably 91.0 mass% or more, for example 98.0 mass% or less, preferably 97.0 mass% or less, based on 100 mass%.
When the content of the (a) tin powder is less than 50.0 mass% in the total amount of the (a) tin powder, (b) epoxy resin, and (c) organic acid compound and (D) curing agent of 100 mass%, the electrical conductivity may be lowered and the volume resistivity may be increased, or when the LED lighting test described in examples a to D is performed, the LED may be unlit and the adhesive strength of the coating film may be lowered beyond 98.0 mass%.
Epoxy resin (b)
As the epoxy resin, all monomers, oligomers, and polymers having 2 or more epoxy groups in the molecular structure can be used, and the molecular weight or molecular structure thereof is not particularly limited. Examples of the epoxy resin used in the present invention include biphenyl type epoxy resins; bisphenol a type epoxy resin, bisphenol F type epoxy resin, tetramethyl bisphenol F type epoxy resin, bisphenol type epoxy resin such as bisphenol type epoxy resin added with propylene oxide; naphthalene type epoxy resin; alkylene oxide modified bisphenol type resin; chelate modified epoxy resin; a stilbene type epoxy resin; novolac type epoxy resins such as phenol novolac type epoxy resins and cresol novolac type epoxy resins; multifunctional epoxy resins such as triphenol methane type epoxy resins and alkyl modified triphenol methane 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; naphthol-type epoxy resins such as dihydroxynaphthalene-type epoxy resins and epoxy resins obtained by subjecting a dihydroxynaphthalene dimer to glycidol etherification; triazine nucleus-containing epoxy resins such as triglycidyl isocyanurate and monoallyl diglycidyl isocyanurate; urethane-modified epoxy resins such as resins obtained by reacting a compound having an isocyanate group and containing a urethane bond with an epoxy compound having a hydroxyl group; bridged cyclic hydrocarbon compound modified phenol type epoxy resins such as dicyclopentadiene modified epoxy resins; dimer acid modified epoxy resins; rubber modified epoxy resin; polysulfide modified epoxy resins; glycidol amine type epoxy resin; glycidyl ester type epoxy resins; etc. Examples of the epoxy resin include alicyclic epoxy resins such as bisphenol compounds such as bisphenol a, bisphenol F, and biphenol or derivatives thereof, and alicyclic polyols such as hydrogenated bisphenol a, hydrogenated bisphenol F, hydrogenated biphenol, cyclohexanediol, cyclohexanedimethanol, and cyclohexanediethanol or epoxides of the derivatives thereof, among compounds having 2 or more epoxy groups in the molecular structure; aliphatic epoxy resins such as epoxides of aliphatic polyols such as butanediol, hexanediol, octanediol, nonanediol, decanediol, polybutadiene polyol and the like or derivatives thereof; an epoxy resin having a triphenylmethane skeleton (triphenolmethane skeleton); aminophenol type epoxy resins and the like; polyether modified epoxy resin; a multifunctional aromatic epoxy resin; hydrogenated bisphenol type epoxy resins, and the like. The epoxy resin may be used alone in 1 kind, or in combination of 2 or more kinds.
The conductive resin composition of the present invention is a composition comprising (b) an epoxy resin,
(I) Is liquid at 25 ℃ and/or,
(Ii) More preferably at least 1 of an aliphatic epoxy resin such as 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, triphenol methane type epoxy resin, naphthalene type epoxy resin, dicyclopentadiene modified epoxy resin, epoxy of aliphatic polyol or derivative thereof, polyether modified epoxy resin, polyfunctional aromatic epoxy resin, and hydrogenated bisphenol type epoxy resin.
Examples of the epoxy resin which is liquid at 25℃include bisphenol-type epoxy resin, naphthalene-type epoxy resin, glycidyl ester-type epoxy resin, glycidyl amine-type epoxy resin, phenol novolac-type epoxy resin, alicyclic epoxy resin such as alicyclic epoxy resin having an ester skeleton, cyclohexane-type epoxy resin, cyclohexanedimethanol-type epoxy resin, glycidyl amine-type epoxy resin, epoxy resin which is an epoxide of polybutadiene polyol, rubber-modified epoxy resin, chelate-modified epoxy resin, urethane-modified epoxy resin, polysulfide-modified epoxy resin, aliphatic epoxy resin such as triphenol methane-type epoxy resin, dicyclopentadiene-modified epoxy resin, epoxy resin of aliphatic polyol or derivative thereof, polyether-modified epoxy resin, polyfunctional aromatic epoxy resin, hydrogenated bisphenol-type epoxy resin, and the like. More preferably, the epoxy resin is at least 1 kind selected from the group consisting of bisphenol type epoxy resins, rubber modified epoxy resins, alicyclic epoxy resins, glycidyl amine type epoxy resins, urethane modified epoxy resins, polysulfide modified epoxy resins, chelate modified epoxy resins, triphenol methane type epoxy resins, naphthalene type epoxy resins, dicyclopentadiene modified epoxy resins, aliphatic epoxy resins such as epoxides of aliphatic polyols and derivatives thereof, polyether modified epoxy resins, polyfunctional aromatic epoxy resins, and hydrogenated bisphenol type epoxy resins.
Specific examples thereof include jER807, jER828US, jER828EL, jER825, jER630LSD, etc. manufactured by mitsubishi chemical company; Adeka Resin EP-4100、Adeka Resin EP-4300E、Adeka Resin EP-4400、Adeka Resin EP-4901E、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 EPU-15F、Adeka Resin EPR-1415-1、Adeka Resin EPR-2000、Adeka Resin EPR-2007、Adeka Resin EP-49-10N、Adeka Resin EP-49-10P2、Adeka Resin EP-49-23、Adeka Glycilol ED-503、Adeka Glycilol ED-503G、Adeka Glycilol ED-506、Adeka Glycilol ED-523T、Adeka Glycilol ED-505 manufactured by ADEKA corporation; FLEP-50, FLEP-60, etc. manufactured by Toli fine chemical Co., ltd; Epolight 40E、Epolight 100E、Epolight 200E、Epolight 400E、Epolight 70P、Epolight 200P、Epolight 400P、Epolight 1500NP、Epolight 1600、Epolight 80MF、Epolight 4000、Epolight 3002(N) manufactured by co-Rong chemical Co., ltd; and Denacol EX-201, denacol EX-201-IM, denacol EX-252, denacol EX-991L, manufactured by Nagase chemtex. These may be used alone or in combination of 1 kind or 2 or more kinds.
Among them, bisphenol type epoxy resin, rubber modified epoxy resin, alicyclic epoxy resin, glycidylamine type epoxy resin, urethane modified epoxy resin, chelate modified epoxy resin, polysulfide modified epoxy resin, triphenolmethane type epoxy resin, naphthalene type epoxy resin and dicyclopentadiene modified epoxy resin are preferably contained from the viewpoints of adhesion, heat resistance, workability, handling property and the like of the obtained conductive resin composition. These may be used singly or in combination of 1 or more than 2.
((B) content of epoxy resin)
In the conductive resin composition of the present invention, the content of the epoxy resin (b) in the conductive resin composition satisfying the above-mentioned requirements (a) is not particularly limited. The total amount of the (a) tin powder, (b) epoxy resin, and (c) organic acid compound is 100% by mass, for example, 0.5% by mass or more, preferably 1.0% by mass or more, more preferably 1.5% by mass or more, for example, 9.8% by mass or less, preferably 8.0% by mass or less, more preferably 7.0% by mass or less.
When the content of (b) epoxy resin in the total amount of (a) tin powder, (b) epoxy resin and (c) organic acid compound is less than 1.0 mass%, there is a concern that film formation may not be possible, the adhesive strength of the coating film may be reduced, when it exceeds 9.5 mass%, there is a concern that conductivity may be reduced and the volume resistivity may be increased, or in the LED lighting test described in examples a to D, there is a concern that the LED may not be lighted.
In the conductive resin composition of the present invention, the content of the epoxy resin (B) in the conductive resin composition satisfying the requirements of the above (B) is not particularly limited. The total amount of the tin powder (a), the epoxy resin (b), the organic acid compound (c) and the curing agent (d) is 100% by mass, for example, 0.5% by mass or more, preferably 1.0% by mass or more, 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, and even more preferably 10.0% by mass or less.
When the content of the (b) epoxy resin in the total amount of 100 mass% of the (a) tin powder, (b) epoxy resin, (c) organic acid compound and (D) curing agent is less than 0.5 mass%, there is a possibility that film formation is impossible, the adhesive strength of the coating film may be lowered, when the adhesive strength exceeds 25.0 mass%, the electrical conductivity may be lowered, the volume resistivity may be raised, or the LED may be unlit in the LED lighting test described in examples a to D.
Organic acid Compound (c)
Examples of the organic acid compound include 1 or 2 or more organic acid compounds represented by R-X n (wherein R is hydrogen or an organic group having 1 to 50 carbon atoms, X is an acid group, and a plurality of X may be different from each other, and n is an integer of 1 or more).
Examples of the acid group represented by X include a carboxyl group (-COOH), a sulfonic acid group (-SO 3 H), a phosphonic acid group (-PO 3H2), and a phosphoric acid group (-PO 4H2).
Examples of the organic acid compound include 1 or more selected from organic carboxylic acid compounds, organic sulfonic acid compounds, and organic phosphonic acid compounds. Organic carboxylic acid compounds are preferred.
(Organic carboxylic acid Compound)
The organic carboxylic acid compound is not particularly limited as long as it has 1 to 50 carbon atoms including 1 or more carboxyl groups (-COOH) in its molecular structure.
As the organic carboxylic acid compound, there is used, examples thereof include acids selected from formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, lauric acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, 12-hydroxystearic acid, ricinoleic acid, oleic acid, octadecadienoic acid, linoleic acid, linolenic acid, arachic acid, behenic acid, lignoceric 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-methylazelaic acid, sebacic acid, dodecanedioic acid, eicosanedioic acid, pelargonic acid, capric acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid dodecenyl succinic acid, citraconic acid, mesaconic acid, itaconic acid, dimethylolpropionic acid, dimethylolbutyric acid, dimethylolvaleric acid, trimethylolpropionic acid, trimethylolbutyric acid, benzoic acid, salicylic acid, pyruvic acid, p-methylbenzoic acid, toluic acid, 4-ethylbenzoic acid, 4-propylbenzoic acid, 2-methylpropanoic acid, isovaleric acid, 2-ethylhexanoic acid, acrylic acid, methacrylic acid, propiolic acid, butenoic acid, 2-ethyl-2-butenoic acid, maleic acid, fumaric acid, oxalic acid, hexanetricarboxylic acid, cyclohexylcarboxylic acid, 1, 4-cyclohexyldicarboxylic acid, ethylenediamine tetraacetic acid, isophthalic acid, terephthalic acid, naphthalene dicarboxylic acid, trimellitic acid, pyromellitic acid, palustric acid, isopimaric acid, and the like.
Further, a linear or branched dicarboxylic acid having 12 or more carbon atoms (for example, SL-12, SL-20, UL-20, MMA-10R, SB-12, IPU-22, IPS-22, SB-20, UB-20, etc. manufactured by Gangcun oil-producing company) may be preferably used.
(Organic sulfonic acid Compound)
The organic sulfonic acid compound is not particularly limited as long as it is a compound having 1 sulfonic acid group (-SO 3 H) in the molecular structure.
Examples thereof include aromatic sulfonic acid compounds selected from the group consisting of benzenesulfonic acid, n-butylbenzenesulfonic acid, n-octylbenzenesulfonic acid, n-dodecylbenzenesulfonic acid, pentadecylbenzenesulfonic acid, 2, 5-dimethylbenzenesulfonic acid, p-chlorobenzenesulfonic acid, p-phenolsulfonic acid, isopropylbenzenesulfonic acid, xylenesulfonic acid, o-cresol sulfonic acid, m-cresol sulfonic acid, p-toluenesulfonic acid, 2-naphthalenesulfonic acid, 1-naphthalenesulfonic acid, styrenesulfonic acid, 4-biphenyldisulfonic acid, anthraquinone-2-sulfonic acid, m-benzenedisulfonic acid, aniline-2, 4-disulfonic acid, anthraquinone-1, 5-disulfonic acid, and polystyrene sulfonic acid; aliphatic sulfonic acid compounds such as methanesulfonic acid, ethanesulfonic acid, 1-propanesulfonic acid, n-octanesulfonic acid, pentadecyl sulfonic acid, trifluoromethanesulfonic acid, trichloromethanesulfonic acid, 1, 2-ethanedisulfonic acid, 1, 3-propanedisulfonic acid, sulfamic acid, and 2-aminoethanesulfonic acid; more than 1 of alicyclic sulfonic acid compounds such as cyclopentane sulfonic acid, cyclohexane sulfonic acid and 3-cyclohexylaminopropanesulfonic acid.
Preferably, 1 or more selected from benzenesulfonic acid, dodecylbenzenesulfonic acid, methanesulfonic acid, p-phenolsulfonic acid, p-toluenesulfonic acid, and (poly) styrenesulfonic acid are exemplified.
(Organic phosphonic acid compound)
The organic phosphonic acid compound is not particularly limited as long as it is a compound having 1 or more phosphonic acid groups (-PO 3H2) in the molecular structure.
Examples thereof include 1 or more selected from 1-hydroxyethylene-1, 1-diphosphonic acid, 1-hydroxypropylene-1, 1-diphosphonic acid, 1-hydroxybutyl-1, 1-diphosphonic acid, aminotrimethylene phosphonic acid, methyldiphosphonic acid, nitrotrimethylene phosphonic acid, ethylenediamine tetramethylene phosphonic acid, ethylenediamine dimethylene phosphonic acid, hexamethylenediamine tetramethylene phosphonic acid, diethylenetriamine pentamethylene phosphonic acid, cyclohexanediamine tetramethylene phosphonic acid, carboxyethyl phosphonic 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, N-dicarboxymethyl-N-methylene phosphonic acid, 2-ethylhexyl phosphate, stearyl alcohol phosphate, and phenylphosphonic acid.
The organic phosphonic acid compound may also be a surfactant having 1 or more phosphate groups (-PO 4H2) within the molecular structure.
As the surfactant having a phosphate group, a surfactant having a polyoxyethylene group or a phenyl group in the molecular structure is preferable. Examples thereof include at least one selected from polyoxyethylene alkylphenyl ether phosphoric acid, polyoxyethylene alkyl ether phosphoric acid, polyoxyethylene oleyl ether phosphoric acid, polyoxyethylene oxypropylene lauryl ether phosphoric acid, polyoxyethylene oxypropylene oleyl ether phosphoric acid, lauryl ammonium phosphate, octyl ammonium phosphate, cetyl ammonium phosphate, polyoxyethylene lauryl ether phosphoric acid, polyoxyethylene oxypropylene lauryl ether phosphoric acid, polyoxypropylene lauryl ether phosphoric acid, polyoxyethylene tristyrylphenyl ether phosphoric acid, polyoxyethylene oxypropylene tristyrylphenyl ether phosphoric acid, polyoxypropylene tristyrylphenyl ether phosphoric acid, and polyoxypropylene tristyrylphenyl ether phosphoric acid.
As the surfactant having a phosphate group, at least 1 of commercial products selected from the group consisting of a commercial product such as Photonol, which is a product of Toho chemical industry Co., ltd, and Disperbyk, which is a product of Pick chemical Co., ltd.
((C) content of organic acid Compound)
In the conductive resin composition of the present invention, the content of the organic acid compound (c) in the conductive resin composition satisfying the requirements of the above (a) is not particularly limited. The total amount of the (a) tin powder, (b) epoxy resin, and (c) organic acid compound is 100% by mass, for example, 0.1% by mass or more, preferably 0.3% by mass or more, 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.
When the content of the organic acid compound (c) in the total amount of (a) tin powder, (b) epoxy resin and (c) organic acid compound is less than 0.1 mass%, there is a concern that film formation is impossible, the adhesive strength of the coating film is lowered, the time required for curing is consumed, etc., and when it exceeds 9.4 mass%, there is a concern that the conductivity is lowered and the volume resistivity is increased, or in the LED lighting test described in examples a to D, there is a concern that the LED is not lit, film formation is impossible, etc.
In the conductive resin composition of the present invention, the content of the organic acid compound (c) in the conductive resin composition satisfying the requirements of the above (B) is not particularly limited. The total amount of the tin powder (a), the epoxy resin (b), the organic acid compound (c) and the curing agent (d) is 100% by mass, for example, 0.1% by mass or more, preferably 0.3% by mass or more, 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.
When the content of the organic acid compound (c) in the total amount of (a) tin powder, (b) epoxy resin, (c) organic acid compound and (D) curing agent is less than 0.1 mass%, there is a concern that film formation is impossible, the adhesive strength of the coating film is lowered, the time required for curing is consumed, etc., and when it exceeds 9.4 mass%, there is a concern that conductivity is lowered and the volume resistivity is raised, or in the LED lighting test described in examples a to D, there is a concern that the LED is not lit, film formation is impossible, etc.
In the conductive resin composition of the present invention, the conductive resin composition satisfying the requirements of (B) contains (d) a curing agent containing 1 or more of (d 1) an acid anhydride curing agent, (d 2) a thiol curing agent and (d 3) a phenol curing agent. The following description will be made with respect to (d 1) an acid anhydride-based curing agent, (d 2) a thiol-based curing agent, and (d 3) a phenol-based curing agent.
(D 1) anhydride-based curing agent
(D1) The acid anhydride-based curing agent is not particularly limited as long as it is a compound having 1 or more carboxylic acid anhydride groups (-C (=o) -o—c (=o) -) in the molecular structure.
(D1) The acid anhydride curing agent is obtained by intermolecular dehydration of the organic carboxylic acid 2 molecules and/or dehydration in the molecular structure of the organic carboxylic acid 1 molecules. In the present invention, for example, 1 or more kinds selected from the group consisting of an acid anhydride obtained by intermolecular dehydration of an organic monocarboxylic acid and an acid anhydride obtained by intramolecular dehydration and/or intermolecular dehydration of an organic polycarboxylic acid among the organic carboxylic acids are exemplified. For example, the aliphatic monocarboxylic acid anhydride, aliphatic polycarboxylic acid anhydride, alicyclic polycarboxylic acid anhydride, aromatic polycarboxylic acid anhydride, or the like may be mentioned as 1 or more kinds.
Preferably, the catalyst is at least one selected from 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, (poly) sebacic anhydride, norbornene-2, 3-dicarboxylic anhydride, methyl-5-norbornene-2, 3-dicarboxylic anhydride, and the like.
In addition, the following structural formula (1) may also be used
[ Chemical formula 2]
( In the structural formula (1), R 1 is a straight-chain or branched-chain hydrocarbon group with a carbon number of 10-40. n is the number of repeating units. )
The polyacid polyanhydride represented. The polyacid polyanhydride is obtained by intermolecular dehydration condensation reaction of long-chain aliphatic dicarboxylic acid.
Specific examples of the polyacid polyanhydride represented by the structural formula (1) include the following structural formulas (2) to (4);
[ chemical formula 3]
The indicated substance.
Examples of polyacid polyanhydrides include 1 or more of SL-12AH, SL-20AH, SB-20AH, IPU-22AH, ST-2PAH, etc. manufactured by Okamura oil Co. In particular, 1 or more of SB-20AH, IPU-22AH and ST-2PAH which are liquid at 25℃are preferable.
The content of the (d 1) acid anhydride-based curing agent in the conductive resin composition is not particularly limited. The acid anhydride group is, for example, 0.05 equivalent or more, preferably 0.1 equivalent or more, for example, 1.5 equivalent or less, preferably 1.3 equivalent or less, and more preferably 1.05 equivalent or less, relative to 1 equivalent of the epoxy group of the epoxy resin. Most preferably 1.0 equivalent. When the amount of the epoxy resin is less than 0.05 equivalent relative to 1 equivalent of the epoxy group, the curability of the conductive resin composition may be reduced, and when the amount of the epoxy resin composition exceeds 1.5 equivalent, the curing of the coating film may be degraded due to the influence of an excessive amount of unreacted curing agent, resulting in a reduction in the hardness of the coating film, and a reduction in the reliability of conductive connection.
The content of the (d 1) acid anhydride-based curing agent in the conductive resin composition may be, for example, 5 parts by mass or more, preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and may be, for example, 250 parts by mass or less, preferably 200 parts by mass or less, more preferably 180 parts by mass or less, based on 100 parts by mass of the epoxy resin. When the content of the acid anhydride-based curing agent (d 1) is less than 5 parts by mass relative to 100 parts by mass of the epoxy resin, the curability of the conductive resin composition may be reduced, and when the content exceeds 250 parts by mass, the conductive resin composition may not be cured and film formation may not be possible.
(D 2) thiol curing agent
The thiol curing agent (d 2) includes thiol compounds having 1 or more thiol groups, preferably 2 or more thiol groups, which are reactive with epoxy groups in the molecular structure. The thiol curing agent (d 2) is preferably a polyfunctional thiol compound having a thiol number of 2 to 6 (2 to 6 functions) in the molecular structure, more preferably a polyfunctional thiol compound having 3 to 6 (3 to 6 functions). The thiol equivalent is not particularly limited, and is, for example, 50g/eq or more, preferably 70g/eq or more, for example, 200g/eq or less, preferably 150g/eq or less, in the low-molecular thiol curing agent. The thiol curing agent of the polymer is 250g/eq or more, preferably 400g/eq or more, for example, 5000g/eq or less, preferably 3000g/eq or less.
Examples of the (d 2) thiol curing agent include trimethylolpropane tris (3-mercaptopropionate) (abbreviated as TMTP), pentaerythritol tetrakis (3-mercaptopropionate) (abbreviated as PEMP), dipentaerythritol hexa (3-mercaptopropionate) (abbreviated as DPMP), tris- [ (3-mercaptopropionyloxy) -ethyl ] -isocyanurate (abbreviated as TEMPIC), tris (3-mercaptopropyl) isocyanurate (abbreviated as TMPIC), ethylene glycol dimercaptoacetate (abbreviated as EGTG), trimethylolpropane trimercaptate (abbreviated as TMTG), pentaerythritol tetramercaptoacetate (abbreviated as PETG), pentaerythritol tetrakis (3-mercaptobutyrate), 1, 4-bis (3-mercaptobutyryloxy) butane, 1,3, 5-tris (3-mercaptobutyryloxy ethyl) -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione, trimethylolpropane tris (3-mercaptobutyrate) (abbreviated as TPMB), trimethylolethane (3, 3-mercaptoethyl) 6-4, 6-mercaptophenylthio-2, 34' -phenylthio-4-isopropyl-1, 4-mercaptocarbamide (abbreviated as 3-mercaptopropyl) and 1, 4-mercaptoisopropyl-4-mercaptophenylthio-4-mercapto3-mercaptoethyl-6-trione Thiol compounds (polyfunctional thiol compounds) such as 1,3, 5-triazine-2, 4, 6-trithiol, polysulfide polymers having a thiol group, and the like. These may be used singly in 1 kind, or in combination of 2 or more kinds.
Specifically, examples thereof include multifunctional thiols (TMMP-LV, PEMP-LV, DPMP, TEMPIC, PEMP, etc.) manufactured by SC organic chemical company, multifunctional thiols (QE-340M, LP-2, LP-3, LP-55, LP-31, etc.) manufactured by Toari fine chemical company, multifunctional thiols (TS-G, C TS-G, etc.) manufactured by Sination chemical industry company, multifunctional thiols (Karenz MT series (PE-1, BD-1, NR-1, TPMB, TEMB, etc.) manufactured by Showa electric company, multifunctional thiols (OTG, EGTG, TMTG, PETG, 3-MPA, TMTP, PETP, etc.), and the like.
The content of the (d 2) thiol 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 1.1 equivalent or less, and even more preferably 1.0 equivalent or less, relative to 1 equivalent of the epoxy group of the epoxy resin. When the amount of the epoxy resin is less than 0.1 equivalent relative to 1 equivalent of the epoxy group, the curability of the conductive resin composition may be reduced, and when the amount of the epoxy resin composition exceeds 1.5 equivalent, the curing of the coating film may be degraded due to the influence of an excessive amount of unreacted curing agent, resulting in a reduction in the hardness of the coating film, and a reduction in the reliability of conductive connection.
The content of the thiol curing agent (d 2) in the conductive resin composition may be, for example, 5 parts by mass or more, preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and may be, for example, 250 parts by mass or less, preferably 200 parts by mass or less, more preferably 180 parts by mass or less, based on 100 parts by mass of the epoxy resin. When the content of the thiol curing agent is less than 5 parts by mass relative to 100 parts by mass of the epoxy resin (d 2), the curability of the conductive resin composition may be reduced, and when the content exceeds 250 parts by mass, the conductive resin composition may not be cured and film formation may not be possible.
(D 3) phenolic curing agent
The phenolic curing agent (d 3) may be a compound having 1 or more, preferably 2 or more phenolic hydroxyl groups in its molecular structure, which can react with an epoxy group. Examples thereof include bisphenols such as bisphenol a, bisphenol B, bisphenol F, bisphenol AD, and bisphenol S; diphenols such as biphenol and tetramethyl biphenol; phenols such as hydroxyphenol and bis (4-hydroxyphenyl) ether; alkylphenols; phenol novolacs such as 2, 6-bis [ (2-hydroxyphenyl) methyl ] -phenol and phenol biphenylene novolacs (biphenylene aralkyl phenols); cresol novolacs such as o-cresol novolacs, m-cresol novolacs and p-cresol novolacs; triphenylmethane; tetraphenols; phenol resins; a phenol novolac resin; biphenyl aralkyl type phenol resin; etc. These may be used singly or in combination of 1 or more than 2.
Specifically, 4', 4' -Trihydroxytriphenylmethane, 4', 4' -methane tetrayl tetraphenol, 1, 2-tetra (4-hydroxyphenyl) ethane, MEH-8005 manufactured by Ming He Chemicals, KAYAHARD GPH-65 manufactured by Japanese chemical Co., ltd., KAYAHARD GPH-103 manufactured by Aica Industrial Co., ltd., BRG-555, BRG-556, BRG-557, BRG-558, CRG-951, TAM-005 and the like.
In the present invention, for example, a phenol resin is preferably used. The hydroxyl equivalent of the phenol resin is, for example, 50g/eq or more, preferably 100g/eq or more, and more preferably 300g/eq or less.
In the present invention, as the phenolic curing agent (d 3), a phenol resin such as phenol novolac is preferably used.
The content of the (d 3) phenolic curing agent in the conductive resin composition is not particularly limited. The phenol group is, for example, 0.1 equivalent or more, preferably 0.2 equivalent or more, for example, 1.5 equivalent or less, preferably 1.2 equivalent or less, more preferably 1.1 equivalent or less, and even more preferably 1.0 equivalent or less, relative to 1 equivalent of the epoxy group of the epoxy resin. When the amount of the epoxy resin is less than 0.1 equivalent relative to 1 equivalent of the epoxy group, the curability of the conductive resin composition may be reduced, and when the amount of the epoxy resin composition exceeds 1.5 equivalent, the curing of the coating film may be degraded due to the influence of an excessive amount of unreacted curing agent, resulting in a reduction in the hardness of the coating film, and a reduction in the reliability of conductive connection.
The content of the (d 3) phenolic curing agent in the conductive resin composition may be, for example, 5 parts by mass or more, preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and may be, for example, 250 parts by mass or less, preferably 200 parts by mass or less, more preferably 180 parts by mass or less, based on 100 parts by mass of the epoxy resin. When the content of the phenolic curing agent is less than 5 parts by mass relative to 100 parts by mass of the epoxy resin (d 3), the curability of the conductive resin composition may be reduced, and when the content exceeds 250 parts by mass, the conductive resin composition may not be cured and film formation may not be possible.
< Other Components >)
The conductive resin composition of the present invention may contain, if necessary, at least one of various additives selected from solvents, adhesion-imparting agents, viscoelastic modifiers, wetting dispersants, curing accelerators (curing catalysts), reactive diluents, conductive powders other than tin powders, resins other than epoxy resins, antioxidants, pigments, fillers (fillers), corrosion inhibitors, defoamers, coupling agents, anti-settling agents, leveling agents, heavy metal deactivators, surfactants, pH adjusters, ultraviolet absorbers, flame retardants, adhesion-imparting agents, and the like.
In the conductive resin composition of the present invention, the conductive resin composition satisfying the requirements of the above (a) may contain 1 or more curing agents for curing the epoxy resin, if necessary.
In the conductive resin composition of the present invention, the conductive resin composition satisfying the requirements of (B) may contain 1 or more curing agents for curing the epoxy resins other than (d 1) to (d 3) as required.
(Solvent)
The conductive resin composition of the present invention may contain a solvent. This improves the fluidity of the conductive resin composition and contributes to improvement of the handleability. Further, by mixing the conductive resin composition with a solvent, a conductive resin paste, a conductive ink, a conductive adhesive, a circuit connecting material, or the like can be constituted.
As the solvent, any solvent selected from 1 or more of water and various organic solvents can be used. Examples of the organic solvent include alcohols selected from ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, 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, ethylcarbitol, butylcarbitol, 2-ethyl-1, 3-hexanediol, methyl methoxybutanol, α -terpineol, β -terpineol, hexylene glycol, benzyl alcohol, 2-phenylethyl alcohol, isopalmitol, isostearyl alcohol, lauryl alcohol, ethylene glycol, propylene glycol, and glycerol; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol (4-hydroxy-4-methyl-2-pentanone), 2-octanone, isophorone (3, 5-trimethyl-2-cyclohexene-1-one), and diisobutyl ketone (2, 6-dimethyl-4-heptanone); ester solvents such as ethyl acetate, butyl acetate, diethyl phthalate, dibutyl phthalate, acetoxyethane, methyl butyrate, methyl caproate, methyl caprylate, methyl caprate, methyl cellosolve acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, ethyldiglycol acetate, and 1, 2-diacetoxyethane; ether solvents such as tetrahydrofuran, dimethyl ether, diethyl ether, dipropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, propylene glycol dimethyl ether, ethoxyethyl ether, 1, 2-bis (2-diethoxy) ethane, and 1, 2-bis (2-methoxyethoxy) ethane; ester ethers such as 2- (2-butoxyethoxy) ethane; ether alcohol solvents such as 2- (2-methoxyethoxy) ethanol; hydrocarbon solvents such as benzene, toluene, xylene, normal paraffins, isoparaffins, dodecylbenzene, turpentine, kerosene, and light oil; nitrile solvents such as acetonitrile and propionitrile; nitrogen-containing polar solvents such as dimethylacetamide, N-dimethylformamide, N-methyl-2-pyrrolidone, and the like; more than 1 kind of silicone oil solvents, etc.
The amount of the solvent used is not particularly limited, and the viscosity of the conductive resin composition may be appropriately adjusted so that the viscosity of the composition may be such that the composition may be properly applied to a substrate, printed on the substrate, or the like, and/or such that the composition may be properly impregnated into a porous body.
(Adhesion-imparting agent)
The conductive resin composition of the present invention may contain an adhesion imparting agent. Thus, when the conductive resin composition is applied to a substrate, adhesion to the substrate and the like can be improved. Examples of the adhesion-imparting agent 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 singly or in combination of 1 or more than 2.
Examples of the adhesion imparting agent include BYK series (4509, 4510, 4512, etc.) manufactured by japan pick chemical company.
(Viscoelastic conditioner)
The conductive resin composition of the present invention may also contain a viscoelastic regulator (rheology control agent). Thus, the viscoelasticity (rheology control agent) of the conductive resin composition can be adjusted, contributing to improvement of workability and the like.
Examples of the viscoelastic regulator (rheology control agent) include viscoelastic regulators (rheology control agents) such as polyamides, aminoplasts, polycarboxylic acids, carbamates, celluloses, and inorganic lamellar compounds. Examples thereof include the RHEOBYK series (H370, H400, H600VF, 100, 405, 410, 411, 415, 430, 431, 440, 7410ET, etc.) manufactured by pike chemical company, japan; disparlon series (AQ-600, AQH-800, 3600N, 3900EF, etc.) manufactured by Nanyou chemical Co., ltd; SN THICKENER series (613, 617, 618, 630, 634, 636, 621N, 623N, etc.) manufactured by Sannopco corporation; adekanol series (UH-814N, UH-752, UH-750, UH-462, etc.) manufactured by ADEKA corporation, and HEC DAICEL series (SP 600N, etc.) manufactured by Daxiu corporation; and BENTONE HD manufactured by ELEMENTIS JAPAN Co. These may be used singly or in combination of 1 or more than 2.
(Wetting dispersant)
The conductive resin composition of the present invention may contain a wetting dispersant as needed to prevent aggregation of tin powder.
Specific examples of the wet dispersant include Solsperse series (9000, 12000, 17000, 20000, 21000, 24000, 26000, 27000, 28000, 32000, 35100, 54000, etc.) manufactured by Lubrizol corporation, EFKA series (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, etc. manufactured by EFKA ADDITIVES corporation, ajisper series (PA 111, PB711, PB821, PB822, PN411, etc.) manufactured by Weisu Fine Techno corporation, DISPRBYK 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. manufactured by Picke chemical corporation, and the like. These may be used singly or in combination of 1 or more than 2.
(Curing accelerator (curing catalyst))
The conductive resin composition of the present invention may contain a curing accelerator (curing catalyst) for accelerating the curing of the epoxy resin and the curing agent. The curing accelerator is not particularly limited, and examples thereof include amine curing accelerators, guanidine curing accelerators, imidazole curing accelerators, phosphonium curing accelerators, and the like. These may be used singly or in combination of 1 or more than 2. Examples thereof include aliphatic tertiary amines such as triethylamine, tripropylamine, tributylamine, dimethylbutylamine, dimethylpentylamine and dimethylcyclohexylamine, dimethylbenzylamine, dimethylaminomethylphenol, dimethylamino-p-cresol, piperidine, α -methylpyridine, pyridine, 4-dimethylaminopyridine, 2,4, 6-tris (dimethylaminomethyl) phenol, 3,4, 5-tris (dimethylaminomethyl) phenol, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, N-aminoethylpiperazine, 1,3, 6-diaminomethylhexane, m-xylylenediamine, p-xylylenediamine, N- (2-aminoethyl) piperazine, m-phenylenediamine, p-phenylenediamine, diaminophenylmethane, methylenedianiline, 2, 4-tolylenediamine, 2, 4-diaminoanisole, 2, 4-tolylenediamine, 2, 4-diaminodiphenylamine, 4' -methylenedianiline, 1, 3-diaminocyclohexane, 3, 9-bis (3-aminopropyl) -2,4,8, 10-tetraspiro [5.5] undecane, 1, 8-diazabicyclo [5.4.0] undecene-7, 1, 5-diazabicyclo [4.3.0] -nonene, Amine compounds such as polyamines, polyamidoamines, polyamides, modified polyamines, modified polyamidoamines, and modified polyamides; guanidine compounds such as dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1- (o-toluene) guanidine, dimethylguanidine, diphenylguanidine, di (o-toluene) guanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5, 7-triazabicyclo [4.4.0] deca-5-ene, 7-methyl-1, 5, 7-triazabicyclo [4.4.0] deca-5-ene, 1-methylguanidine, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1-dimethylbiguanide, 1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, and 1- (o-toluene) biguanide; phosphonium compounds such as tetraphenyl phosphonium bromide, tetrabutylphosphonium bromide, butyltriphenyl phosphonium bromide, tetraphenyl phosphonium iodide, tetrabutylphosphonium iodide, butyltriphenyl phosphonium iodide, tetraphenyl phosphonium tetraphenyl borate, tetrabutylphosphonium tetrabutylborate, butyltriphenyl phosphonium tetrabutylborate, tetraphenyl phosphonium acetate, tetrabutylphosphonium acetate, butyltriphenyl phosphonium acetate, tetrabutylphosphonium tetrafluoroborate, tetrabutylphosphonium hexafluorophosphate, methyltributylphosphonium dimethyl phosphate, tetrabutylphosphonium acetate, tetrabutylphosphonium hydroxide and the like: a compound containing an transition metal such as titanium or cobalt; etc. These may be used singly or in combination of 1 or more than 2.
(Reactive diluent)
The conductive resin composition of the present invention may contain a reactive diluent for adjusting the viscosity of the conductive resin composition, adjusting the curability, or the like. The reactive diluent is not particularly limited, and examples thereof include 1 or more compounds having 1 epoxy group in the molecular structure, compounds having 1 or more oxetanyl groups in the molecular structure, and the like. Examples thereof include glycidyl phenyl ether, glycidyl lauryl ether, 2-phenylphenol glycidyl ether, allyl glycidyl ether, 4-t-butylphenyl glycidyl ether, N-glycidyl phthalimide, 2-ethylhexyl glycidyl ether, YED111N, YED AN manufactured by Mitsubishi chemical corporation, YED188, denacol EX-145 manufactured by Adeka Glycilol ED-502、Adeka Glycilol ED-502S、Adeka Glycilol ED-509E、Adeka Glycilol ED-509S、Adeka Glycilol ED-529、Nagasechemtex corporation of ADEKA, denacol EX-171, denacol EX-192, epoligo M-1230 manufactured by Kagrong chemical corporation, epoligo 100MF, aron Oxetane OXT-101 manufactured by east Asian synthetic corporation, aron Oxetane OXT-212, aron Oxetane OXT-121, aron Oxetane OXT-221, ETERNACOLL EHO, ETERNACOLL HBOX, ETERNACOLL OXMA and ETERNACOLL OXBP manufactured by UBE corporation. These may be used singly or in combination of 1 or more than 2.
(Conductive powder)
The conductive resin composition of the present invention may contain conductive powder other than tin powder. Examples of the conductive powder include 1 or more selected from lead-free solder powder, gold alloy powder, silver alloy powder, copper alloy powder, silver-coated copper alloy powder, silver-coated silica 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 nanotubes, graphene, and the like.
For example, the lead-free solder powder is not particularly limited as long as it is a powder containing no solder containing lead in an amount not less than an unavoidable amount, in view of influences on an operator, a user, the environment, and the like. The melting point of the lead-free solder powder is preferably 300 ℃ or less, more preferably 240 ℃ or less, and still more preferably 50 to 240 ℃. When the melting point of the lead-free solder powder exceeds 300 ℃, there is a concern that the circuit board, the electronic component, or other connected members may thermally break or thermally deteriorate. When the melting point is lower than 50 ℃, the mechanical strength becomes weak, and the reliability of the conductive connection may be lowered.
(Resin)
The conductive resin composition of the present invention may contain a resin other than an epoxy resin. As such a resin, either a thermoplastic resin or a thermosetting resin may be used, and 1 or 2 or more kinds may be used.
Examples of the thermoplastic resin include at least 1 selected from the group consisting of polyvinyl butyral resins, acrylic resins, polyester resins, phenol resins, polyimide resins, polyolefin resins, thermoplastic polyurethane resins, polyamide resins, polycarbonate resins, polyphenylene ether resins, polyvinyl alcohol resins, polyvinyl acetate resins, ionomer resins, polyvinylpyrrolidone resins, and terpene resins.
Examples of the thermosetting resin include 1 or more selected from resol-type phenol resins, polyimide-type resins, xylene-type resins, polyurethane-type resins, melamine-type resins, urea-type resins, furan resins, isocyanate-type resins, and urea resins.
In the present invention, the resin preferably contains 1 or more kinds selected from the group consisting of polyvinyl butyral resins, resol-type phenol resins, acrylic resins, polyester resins, phenoxy resins, polyimide resins, and xylene resins. Among them, polyvinyl butyral resins are preferably used from the viewpoints of film formation, connection reliability, adhesion to a substrate, and the like.
(Antioxidant)
The conductive resin composition of the present invention may contain an antioxidant. This can contribute to improvement in heat resistance, yellowing resistance, and the like of the cured product of the conductive resin composition. The antioxidant is not particularly limited as long as it is a compound having a function of preventing oxidation, and known or conventional antioxidants can be used. Examples thereof include phenolic antioxidants such as hindered phenol compounds, quinone antioxidants such as hydroquinone, phosphorus antioxidants, sulfur antioxidants, hindered amine antioxidants such as hindered amine compounds, and the like. These may be used singly or in combination of 1 or more than 2. Examples thereof include those selected from 2, 2-methylene-bis (4-methyl-6-t-butylphenol), catechol, t-butylcatechol, 2-butyl-4-hydroxyanisole, 2, 6-di-t-butyl-p-cresol, 2, 4-di-t-butyl-6-methylphenol, 2-t-butyl-4-methylphenol, 2, 4-di-t-butylphenol, 2, 4-di-t-pentylphenol, bis- [3, 3-bis- (4 '-hydroxy-3' -t-butylphenyl) -butanoic acid ] -glycol ester, 2-t-butyl-6- (3-t-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' -butylidenebis (6-tert-butyl-3-methylphenol), 2' -butylidenebis (4, 6-di-tert-butylphenol), 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 '-hexane-1, 6-diylbis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionamide ], phenylpropionic acid, 3, 5-bis (1, 1-dimethylethyl) -4-hydroxy, C 7~C9 side chain alkyl ester, 2, 4-dimethyl-6- (1-methylpentadecyl) phenol, diethyl [ [3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] phosphate, 3',3",5, 5', 5' -hexa-tert-butyl-a, a ' - (mesitylene-2, 4, 6-toluene) tris-p-cresol, calcium diethyl bis [ [3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] phosphate, 4, 6-bis (octylthiomethyl) o-cresol, ethylene bis (oxyethylene) bis [3- (5-tert-butyl-4-hydroxy-m-toluene) propionate ], triethylene glycol-bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate ], hexamethylene bis [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-triazin-2, 4,6 (1H, 3H, 5H) -trione, 1,3, 5-tris [ (4-tert-butyl-3-hydroxy-2, 6-xylyl) methyl ] -1,3, 5-triazin-2, 4,6 (1H, 3H, 5H) -trione, the reaction product of N-phenylaniline with 2,4, 6-trimethylpentene, 2, 6-di-tert-butyl-4- (4, 6-bis (octylthio) -1,3, 5-triazin-2-ylamino) phenol, Phenolic antioxidants such as picric acid and citric acid; quinone antioxidants such as beta-naphthoquinone, 2-methoxy-1, 4-naphthoquinone, methylhydroquinone, hydroquinone monomethyl ether, mono-t-butylhydroquinone, 2, 5-di-t-butylhydroquinone, p-benzoquinone, 2, 5-diphenyl-p-benzoquinone, 2, 5-di-t-butyl-p-benzoquinone; tris (2, 4-di-tert-butylphenyl) phosphite, tris [2- [ [2,4,8, 10-tetra-tert-butyldibenzo [ d, f ] [1,3,2] dioxaphosphepin-6-yl ] oxy ] ethyl ] amine, bis (2, 4-di-tert-butylphenyl) pentaerythritol diphosphite, bis [2, 4-bis (1, 1-dimethylethyl) -6-methylphenyl ] ethyl phosphite, tetrakis (2, 4-di-tert-butylphenyl) [1, 1-diphenyl ] -4,4' -diyl bisphosphonate, 6- [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propoxy ] -2,4,8, phosphorus antioxidants such as 10-tetra-tert-butyldibenzo [ d, f ] [1,3,2] dioxaphosphepin; sulfur-based antioxidants such as dilauryl 3,3' -thiodipropionate, dimyristoyl 3,3' -thiodipropionate, distearyl 3,3' -thiodipropionate, pentaerythritol tetrakis (3-laurylthiopropionate), and 2-mercaptobenzimidazole; amine antioxidants such as phenothiazine; a lactone antioxidant; more than 1 of vitamin E antioxidants, etc.
The antioxidant may be commercially available. Examples thereof include IRGANOX series manufactured by BASF corporation, ADK STAB series manufactured by ADEKA corporation, nonflex series manufactured by Seiko chemical corporation, sumilizer series manufactured by Sumitomo chemical corporation, and the like.
(Curing agent for curing epoxy resin)
The conductive resin composition of the present invention may contain a curing agent for curing the epoxy resin, if necessary, in the conductive resin composition satisfying the requirements of (a). Examples of the curing agent for curing the epoxy resin include 1 or more selected from acid anhydride-based curing agents, thiol-based curing agents, phenol-based curing agents, amine-based curing agents, amide-based curing agents, and the like. The conductive resin composition of the present invention preferably contains a curing agent that is liquid at 25 ℃ from the viewpoint of more effectively improving workability, handleability, and the like. In the conductive resin composition of the present invention, when an amine-based curing agent is used as a curing agent for curing the epoxy resin, any one or more of an acid anhydride-based curing agent, a thiol-based curing agent and a phenol-based curing agent may be used in combination in the conductive resin composition satisfying the above-mentioned requirements (a).
The conductive resin composition of the present invention satisfying the requirements of (B) may contain a curing agent for curing an epoxy resin other than the above (d 1) to (d 3), if necessary. Examples of such a curing agent include 1 or more kinds selected from amine-based curing agents and amide-based curing agents. The conductive resin composition of the present invention preferably contains a curing agent that is liquid at 25 ℃ from the viewpoint of more effectively improving workability, handleability, and the like.
The conductive resin composition satisfying the requirements of (a) may contain, as necessary, an acid anhydride-based curing agent, a thiol-based curing agent and a phenol-based curing agent, which are the same curing agents as the acid anhydride-based curing agent (d 1), the thiol-based curing agent (d 2) and the phenol-based curing agent (d 3), respectively.
Amine curing agent
Examples of the amine curing agent among the curing agents which may be optionally contained in the conductive resin composition of the present invention for curing an epoxy resin include diethylenetriamine, triethylenetetramine, diethylaminopropylamine, menthanediamine, isophoronediamine, bis [ 4-amino-3-methyldicyclohexyl ] methane, diaminodicyclohexylmethane, bis (aminomethyl) cyclohexane, m-xylylenediamine, m-phenylenediamine, diaminodiphenylmethane, diaminodiethyldiphenylmethane, and modified polyamines obtained by modifying these by epoxy addition, michael addition, mannich reaction, and the like. These may be used singly or in combination of 1 or more than 2.
Content of curing agent for curing epoxy resin
In the conductive resin composition of the present invention, the content of the curing agent for curing the epoxy resin in the conductive resin composition satisfying the requirements of the above (a) is not particularly limited. In the conductive resin composition satisfying the requirements of the above (a), the conductive resin composition can be cured without using a curing agent.
When the conductive resin composition satisfying the requirements of (a) contains a curing agent, the group (e.g., hydroxyl group, thiol group, amino group, acid anhydride group, etc.) that reacts with the epoxy group in the curing agent 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 equivalent or less, based on 1 equivalent of the epoxy group in the epoxy resin. Most preferably 1.0 equivalent. When the epoxy group content is less than 0.1 equivalent, the curability of the conductive resin composition satisfying the above-mentioned requirement (a) may be reduced, and when the epoxy group content exceeds 1.5 equivalent, there is a possibility that the curing time is consumed for curing or the curing failure of the coating film occurs, and when the epoxy group content exceeds 1.1 equivalent, the curing failure of the coating film occurs due to the influence of the excessive unreacted curing agent, the coating film hardness may be reduced, and the reliability of the conductive connection may be reduced.
In the conductive resin composition satisfying the requirements of (a), the total amount of the curing agent with respect to 100 parts by mass of the epoxy resin may be, for example, 5 parts by mass or more, preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and 250 parts by mass or less, preferably 200 parts by mass or less, more preferably 180 parts by mass or less. When the total amount of the curing agent is less than 5 parts by mass relative to 100 parts by mass of the epoxy resin, the curability of the conductive resin composition satisfying the above-mentioned requirement (a) may be reduced, and when the curing time is more than 250 parts by mass, the conductive resin composition may not be solid.
In the conductive resin composition of the present invention, the content of the curing agent for curing the epoxy resin other than the curing agents of (d 1) to (d 3) in the conductive resin composition satisfying the requirements of (B) is not particularly limited. In the conductive resin composition satisfying the requirements of (B), a curing agent for curing the epoxy resin other than the above (d 1) to (d 3) may not be used.
When the curing agent for curing an epoxy resin other than the curing agents (d 1) to (d 3) is contained, the group (for example, hydroxyl group, amino group, amide group, etc.) which reacts with the epoxy group in the curing agent 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 equivalent or less, based on 1 equivalent of the epoxy group in the epoxy resin. Most preferably 1.0 equivalent. When the epoxy group content is less than 0.1 equivalent, the curability of the conductive resin composition satisfying the above-mentioned requirement (a) may be reduced, and when the epoxy group content exceeds 1.5 equivalent, there is a possibility that the curing time is consumed for curing or the curing failure of the coating film occurs, and when the epoxy group content exceeds 1.1 equivalent, the curing failure of the coating film occurs due to the influence of the excessive unreacted curing agent, the coating film hardness may be reduced, and the reliability of the conductive connection may be reduced.
In the conductive resin composition satisfying the requirements of (B), the total amount of the curing agent with respect to 100 parts by mass of the epoxy resin may be, for example, 5 parts by mass or more, preferably 10 parts by mass or more, more preferably 15 parts by mass or more, and 250 parts by mass or less, preferably 200 parts by mass or less, more preferably 180 parts by mass or less. When the content of the curing agent is less than 5 parts by mass relative to 100 parts by mass of the epoxy resin, the curability of the conductive resin composition may be reduced, and when the content exceeds 250 parts by mass, the conductive resin composition satisfying the requirements of the above (B) may not be formed into a solid.
Property of conductive resin composition
The properties of the conductive resin composition of the present invention may be any of powder, solid, paste, liquid (varnish), and the like. In the case of use as a conductive ink, a conductive adhesive, or a circuit connecting material, it is preferably in the form of a paste or liquid (varnish) at room temperature (25 ℃).
When the conductive resin composition of the present invention is prepared by mixing and stirring materials by a mixer or the like into a paste-like or liquid-like (varnish-like) conductive resin composition, a uniform conductive resin composition can be formed without causing caking or the like.
Property of conductive resin composition
The conductive resin composition of the present invention has excellent curability. For example, after the coating on a substrate, a conductive film (dry coating film) can be easily formed by heat treatment (calcination) at 50 to 250 ℃ for 5 to 300 minutes.
The conductive resin composition of the present invention is excellent in conductivity. For example, the volume resistivity of the conductive film obtained by drying and peeling the conductive resin composition by casting or coating on a releasable substrate is lower than 1.0X10 -2 Ω cm. The volume resistivity of the conductive film is preferably less than 8.0X10 -3 Ω·cm, more preferably less than 1.0X10 -3 Ω·cm. Here, the volume resistivity was obtained by the method in examples a to D.
The surface of the cured product of the conductive resin composition of the present invention may exhibit insulation properties, but may exhibit good electrical conductivity. For example, when the conductive resin composition is used for bonding the connection members, even if the film of the conductive resin composition has surface insulation (volume resistivity of 1.0X10 -1 Ω·cm or more and the surface is substantially an insulator), conductive connection can be formed between the connection members because the inside exhibits conductivity. The confirmation of the formation of the conductive connection can be confirmed by the LED lighting test described in examples a to D. Thus, it is considered that the surface of the cured product of the conductive resin composition exhibits insulation and the inside thereof exhibits conductivity, and a general structure of the electric wire with an insulating film is formed.
The conductive resin composition of the present invention is excellent in adhesion to various substrates. For example, the adhesive property with respect to glass, metal or plastic (for example, polyester or the like) is excellent.
The conductive resin composition of the present invention has practical storage stability that allows coating, printing, and the like even after production and storage.
Process for producing conductive resin composition
In the conductive resin composition of the present invention, when the conductive resin composition satisfying the above-mentioned requirements of (a) is prepared, in addition to (a) tin powder, (b) epoxy resin and (c) organic acid compound as essential components, additives listed in the above-mentioned < other components > may be added to the mixing vessel in any order as required (for example, 1 or more selected from solvents, adhesion imparting agents, viscoelastic modifiers, wetting dispersants, curing accelerators (curing catalysts), reactive diluents, conductive powders other than tin powder, resins other than epoxy resin, antioxidants, curing agents, pigments, fillers (fillers), corrosion inhibitors, antifoaming agents, coupling agents, anti-settling agents, leveling agents, heavy metal deactivators, surfactants, pH modifiers, ultraviolet absorbers, flame retardants, adhesion imparting agents, and the like) and the like are mixed.
In the conductive resin composition of the present invention, when the conductive resin composition satisfying the requirements of (B) is prepared, in addition to the tin powder (a), the epoxy resin (B), the organic acid compound (c), and the curing agent (d) as the essential components, the additives listed in the above < other components > may be added to the mixing vessel in any order as required (for example, at least 1 selected from a solvent, an adhesion-imparting agent, a viscoelastic modifier, a wetting dispersant, a curing accelerator (curing catalyst), a reactive diluent, a conductive powder other than tin powder, a resin other than epoxy resin, an antioxidant, a curing agent, a pigment, a filler (filler), a corrosion inhibitor, an antifoaming agent, a coupling agent, an anti-settling agent, a leveling agent, a heavy metal passivating agent, a surfactant, a pH adjuster, an ultraviolet absorber, a flame retardant, an adhesive, and the like) and the like are mixed.
In the mixing, for example, a method of mixing by a rotation/revolution mixer, a ball mill, a roll mill, a bead mill, a planetary mixer, a roller, a stirrer, a mechanical homogenizer, an ultrasonic homogenizer, a high-pressure homogenizer, a paint stirrer, a V-type mixer, a Nauta mixer, a Banbury mixer, a kneading roll, a single-shaft extruder, a twin-shaft extruder, or the like can be suitably used.
The temperature at which the conductive resin composition is prepared (the temperature at which the components are mixed) is not particularly limited. If necessary, heating or the like may be performed, for example, to prepare the conductive resin composition at 10 to 100 ℃.
The atmosphere in preparing the electroconductive resin composition is not particularly limited. The method can be carried out in the atmosphere or under an inert gas atmosphere.
Use of conductive resin composition
The use of the conductive resin composition of the present invention is related to the production of a conductive object. The conductive object may contain other members in addition to the conductive resin composition.
Examples of the conductive objects include at least one selected from conductive inks, circuit connection materials, conductive pastes, conductive films having conductivity, conductive fibers, conductive paints, conductive materials for semiconductor packages, conductive materials for microelectronic devices, antistatic materials, electromagnetic wave shielding materials, conductive adhesives (adhesives for surface mount component mounting, etc.), die attach pastes, regulators, sensors, conductive resin molded bodies, electrode forming materials for electronic components (terminals for chip resistors, etc.), internal electrode materials for electronic components (internal electrodes for MLCCs, etc.), collector materials, antenna forming materials, and the like.
For example, a conductive ink, a conductive paste, a conductive paint, a conductive adhesive, or the like can be formed by using a solvent as a component of the conductive resin composition. The viscosity in this case is not particularly limited, and a varnish-like form having a low viscosity to a paste-like form having a high viscosity can be prepared according to the application and the like.
For example, the conductive resin composition containing a solvent or the like as required is applied to various substrates by a casting method, a dipping method, a bar coating method, a spreading method, a roll coating method, a gravure coating method, gravure printing, screen printing, a flexographic printing method, a spray coating method, a spin coating method, an inkjet method, lithography, gravure lithography, a slit coating method, a knife coating method, a pad printing method, a resin embossing, an applicator method, reverse printing, reverse lithography, or the like, and is heated and dried at a temperature of 300 ℃ or less to produce a conductive film. The atmosphere at the time of drying may be 1 or more selected from the group consisting of the atmosphere, inert gas, vacuum, reduced pressure, and the like. An inert gas atmosphere such as nitrogen or argon is particularly preferable from the viewpoint of suppressing deterioration of the film having conductivity (preventing oxidation of tin powder or the like).
The conductive resin composition of the present invention can be molded by molding methods such as extrusion molding, injection molding, compression molding, vacuum molding, pressure molding, vacuum pressure molding, blow molding, TOM molding, compression molding, insert molding, and in-mold molding, and can be used as a molded article. Examples of the molded article include electronic parts, automobile parts, mechanical parts, food containers, films, sheets, and fibers.
[ Conductive film ]
The conductive film of the present invention is formed from the conductive resin composition and has a volume resistivity of less than 1.0X10 -2. Omega. Cm. The volume resistivity of the conductive film is preferably less than 1.0X10 -3. Omega. Cm, more preferably 8.0X10 -4. Omega. Cm or less, and still more preferably 3.0X10 -4. Omega. Cm or less. The conductive film of the present invention can be formed to have a volume resistivity of less than 1.0X10 -4Ω·cm(10-5 Ω·cm), which is comparable to that of a conductive film formed of silver paste.
Here, the volume resistivity can be obtained by the methods described in examples a to D.
The method for forming the conductive film from the conductive resin composition is not particularly limited. For example, the conductive resin composition may contain a solvent, and a conductive film may be formed by applying the solvent to an arbitrary substrate, drying the same, and the like. The conductive resin composition may be obtained by casting or coating the conductive resin composition on a releasable substrate, drying the coated conductive resin composition, and then releasing the coated conductive resin composition.
The conditions for forming the conductive film are not particularly limited, and may be appropriately set according to the object to be coated or the like. The temperature after the application of the conductive resin composition, such as drying, is, for example, 50 ℃ or higher, preferably 90 ℃ or higher, for example, 250 ℃ or lower, preferably 220 ℃ or lower. The time for drying or the like is, for example, 5 minutes or more, preferably 7 minutes or more, for example, 300 minutes or less, preferably 200 minutes or less.
The dry film thickness of the conductive film is not particularly limited and may be appropriately adjusted according to the application or the like. For example, 10 μm or more, preferably 30 μm or more, for example, 1000 μm or less, preferably 500 μm or less.
[ Conductive ink ]
The conductive ink of the present invention contains the conductive resin composition. For example, the conductive resin composition may be dissolved and/or dispersed in the solvent as needed.
The conductive ink of the present invention may further contain, if necessary, an additive (for example, at least one selected from the group consisting of a solvent, an adhesion-imparting agent, a viscoelastic modifier, a wetting dispersant, a curing accelerator (curing catalyst), a reactive diluent, a conductive powder other than tin powder, a resin other than epoxy resin, a curing agent, an antioxidant, a pigment, a filler (filler), a corrosion inhibitor, an antifoaming agent, a coupling agent, an anti-settling agent, a leveling agent, a heavy metal deactivator, a surfactant, a pH modifier, an ultraviolet absorber, a flame retardant, an adhesion-imparting agent, and the like) as listed in the above-mentioned < other component >.
The conductive ink is obtained by: after the above components are put into a mixing vessel, they are prepared into varnish or paste using a mixer of 1 or more kinds selected from a rotation/revolution mixer, a ball mill, a roller mill, a bead mill, a planetary mixer, a roller, a stirrer, a mechanical homogenizer, an ultrasonic homogenizer, a high-pressure homogenizer, a paint stirrer, a V-type mixer, a Nauta mixer, a Banbury mixer, a kneading roll, a single-screw extruder, a twin-screw extruder, and the like.
The conductive ink can be used, for example, as a conductive ink for printing for forming a wiring. The method for applying the conductive ink to various substrates is not particularly limited. For example, a method of applying the conductive resin composition to a substrate may be mentioned. In the present invention, for example, 1 or more selected from screen printing, ink jet printing, flexographic printing, gravure printing, and the like is preferable, and from the viewpoint of excellent printability and shape retention, 1 or more printing methods selected from screen printing, ink jet printing, and the like are more preferable.
The mesh in the screen printing method may be appropriately selected, and it is preferable to use a mesh that does not excessively remove the conductive powder or the lead-free solder powder in the conductive ink.
The film thickness of the coating film obtained by applying the conductive ink may be set to an appropriate film thickness according to various applications. For example, 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 at least 1 property selected from the group consisting of conductivity, adhesion to various substrates, leveling (surface smoothness), printability, and the like.
[ Conductive adhesive ]
The conductive adhesive of the present invention contains the conductive resin composition. For example, the conductive resin composition may be dissolved and/or dispersed in the solvent as needed.
The conductive adhesive of the present invention may further contain, if necessary, an additive (for example, at least one selected from the group consisting of a solvent, an adhesion-imparting agent, a viscoelastic modifier, a wetting dispersant, a curing accelerator (curing catalyst), a reactive diluent, a conductive powder other than tin powder, a resin other than epoxy resin, a curing agent, an antioxidant, a pigment, a filler (filler), a corrosion inhibitor, an antifoaming agent, a coupling agent, an anti-settling agent, 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) as listed in the above < other component >.
The conductive adhesive is obtained by: after the above components are put into a mixing vessel, they are prepared into varnish or paste using a mixer of 1 or more kinds selected from a rotation/revolution mixer, a ball mill, a roller mill, a bead mill, a planetary mixer, a roller, a stirrer, a mechanical homogenizer, an ultrasonic homogenizer, a high-pressure homogenizer, a paint stirrer, a V-type mixer, a Nauta mixer, a Banbury mixer, a kneading roll, a single-screw extruder, a twin-screw extruder, and the like.
The conductive adhesive of the present invention is used for bonding so that the bonding target portion has conductivity. For example, in the production of batteries, electric and electronic devices, the battery can be used for adhesion requiring conductivity.
The conductive adhesive of the present invention can be used as an anisotropic conductive adhesive. Thus, highly reliable conductive connection can be formed in the miniaturization of electronic parts such as IC chips and light emitting diodes, electrode connection of circuit boards, and the like. The conductive adhesive of the present invention may be advantageous in mounting electronic components at a high density because the surface of the cured film after curing exhibits insulation.
Examples of the adhesive structure to be adhered to each other by the adhesive member with the conductive adhesive of the present invention include an RFID-related product such as an IC card or an IC tag, in which an IC wafer is adhered to a substrate having an electrode, and a light-emitting electronic component in which a light-emitting diode is adhered to a substrate having an electrode. For example, a plurality of electrodes are formed on at least one surface of a substrate, and the conductive adhesive of the present invention is applied so as to cover at least each electrode to form an adhesive film, and electrode portions of each electronic component are pressed against each electrode portion, and the adhesive layer is used to cure the electrode portions, thereby forming an adhesive structure using the conductive adhesive.
The method of applying the conductive adhesive of the present invention to a substrate is not particularly limited. For example, a method of applying the conductive resin composition to a substrate may be mentioned. In the present invention, printing, ejection, and the like can be performed. The printing method is preferably 1 or more selected from screen printing, ink jet printing, flexographic printing, gravure printing, and the like, and from the viewpoint of excellent printability and shape retention, it is preferable to use 1 or more selected from screen printing, ink jet printing, and the like.
Here, the mesh in screen printing can be appropriately selected, and it is preferable to use a mesh that does not excessively remove the conductive powder in the conductive adhesive.
The film thickness of the adhesive film to which the conductive adhesive is applied may be set to an appropriate film thickness according to various applications. For example, 1 μm or more, preferably 2 μm or more, more preferably 5 μm or more, and 200 μm or less.
The conductive adhesive of the present invention may be used after being formed into a film. The film-like conductive adhesive can be obtained, for example, by a method of applying a conductive adhesive solution obtained by adding a solvent or the like to a conductive adhesive composition or the like as needed to a releasable support and removing the solvent or the like. The film-like conductive adhesive is more convenient in terms of handling and the like. 1 or more layers of film-like conductive adhesive may be used as the multilayer structure together with 1 or more layers of insulating adhesive, 1 or more layers of releasable material, and the like as required.
The conductive adhesive of the present invention can be used to bond the adherends to each other by heating and pressurizing. The heating temperature is not particularly limited as long as it is within a range that does not damage the adherend, and is, for example, 70 ℃ to 250 ℃. The pressure is not particularly limited as long as it is within a range that does not damage the adherend, and is, for example, 0.1MPa to 10 MPa. The heating and pressurizing are preferably performed for, for example, 0.5 seconds to 120 seconds.
The conductive adhesive of the present invention can be used for electrically bonding adherends to each other. For example, the adhesive can be used as an adhesive for bonding different types of adherends having different coefficients of thermal expansion, which are materials different from each other, to each other, and electrically connecting the adherends. The conductive adhesive of the present invention can be used as a circuit connecting material such as an anisotropic conductive adhesive, a conductive paste, or a conductive adhesive film, or a semiconductor element adhesive material such as an underfill material or LOC tape.
[ Circuit connecting 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 further contain, if necessary, an additive (for example, at least one selected from the group consisting of a solvent, an adhesion-imparting agent, a viscoelastic modifier, a wetting dispersant, a curing accelerator (curing catalyst), a reactive diluent, a conductive powder other than tin powder, a resin other than epoxy resin, a curing agent, an antioxidant, a pigment, a filler (filler), a corrosion inhibitor, an antifoaming agent, a coupling agent, an anti-settling agent, 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) as listed in the above-mentioned < other component >.
The circuit connecting material of the present invention can be used for electrically connecting various electronic components and circuit boards or electrically connecting (bonding) electric and electronic circuits to each other.
The shape of the circuit-connecting material is not particularly limited, and is preferably liquid or film.
The liquid circuit-connecting material can be obtained by, for example, mixing a solvent such as an organic solvent into the conductive resin composition of the present invention.
The film-shaped circuit connecting material can be obtained, for example, by directly casting and coating the above-mentioned liquefied conductive resin composition of the present invention on a releasable substrate to form a film, drying to remove the solvent, and then peeling the film from the releasable substrate.
The film-shaped circuit-connecting material may be obtained by impregnating the above-mentioned liquefied conductive resin composition of the present invention with a nonwoven fabric or the like, forming the resin composition on a releasable substrate, drying the resin composition to remove the solvent, and then peeling the resin composition from the releasable substrate.
The electrical connection method using the circuit connection material and the like are not particularly limited. For example, a method of providing a circuit connecting material between electrodes of an electronic component, a circuit, or the like and electrodes on a substrate facing the electrodes, and heating the circuit connecting material to electrically connect the electrodes and bond the electrodes to each other can be exemplified. When heating, pressurization may be performed as needed.
The method for providing the circuit connecting material between the opposing electrodes is not particularly limited. Examples of the method include a method of applying a liquid circuit-connecting material and a method of inserting a film-like circuit-connecting material.
In addition, when a plug of an electronic component or the like is electrically connected to a circuit, a circuit connecting material is provided at the root of the plug, and the conductive connection is formed by bonding.
The circuit connecting material is used as an anisotropic conductive material, and is also useful for forming a circuit connecting material excellent in adhesion between electrodes facing each other on a substrate, and for obtaining contact between both electrodes and adhesion between substrates by heating and pressurizing. As the substrate for forming the electrode, various combinations of inorganic substances such as semiconductors, glasses, ceramics, and the like, organic substances such as polyimide, polycarbonate, and the like, and such composites such as epoxy glass and the like can be applied.
Examples
The present invention will be described in further detail with reference to the following examples. The present invention is not limited to these examples. Unless otherwise specified, "%" means "% by mass", and "parts" means "parts by mass".
Example A
Example a is an example of a conductive resin composition satisfying the requirement of (a) in the conductive resin composition of the present invention.
The components and substrates used in example a are shown below.
Tin powder A1: spherical tin powder (D50=5.5 μm, sn. Gtoreq.99.5% by mass)
Tin powder A2: irregularly shaped tin powder (d50=7.5 μm, sn+.99.9 mass%)
Copper powder a: spherical copper powder (particle size 10 μm to 25 μm, manufactured by Sigma-Aldrich Co., ltd., copper powder (spherical), 98%)
Nickel powder a: irregularly shaped nickel powder (D90:10 μm or less)
Epoxy resin A1: bisphenol type epoxy resin (jor 1001 manufactured by mitsubishi chemical Co., ltd.)
Epoxy A2: bisphenol type epoxy resin (jor 1004 manufactured by mitsubishi chemical Co., ltd.)
Epoxy A3: toughened epoxy resin (LCE-2615, manufactured by Japanese chemical Co., ltd.)
Epoxy A4: triphenol methane type epoxy resin (EPPN-501H, manufactured by Japanese chemical Co., ltd.)
Epoxy A5: bisphenol type epoxy resin (jor 828 manufactured by Mitsubishi chemical corporation)
Epoxy A6: rubber modified epoxy resin (manufactured by ADEKA Co., ltd., EPR-1415-1)
Epoxy A7: propylene oxide to bisphenol type epoxy resin (manufactured by ADEKA Co., ltd., EP-4000S)
Organic acid compound A1: glutaric acid
Organic acid compound A2: liquid polycarboxylic acid (MMA-10R manufactured by Okamura oil Co., ltd.)
Organic acid compound A3: pimelic acid
Solvent A1: dipropylene glycol monomethyl ether
Solvent A2: ethyl carbitol
Solvent A3: ethyldiglycol acetate
Solvent A4: 2-ethyl-1, 3-hexanediol
Solvent A5: ethylene glycol
Adhesion promoter A1: BYK4512 (manufactured by Pick chemical Co., ltd.)
Viscoelastic regulator A1: RHEOBYK-405 (manufactured by Pick chemical Co., ltd., japan)
Viscoelasticity modifier A2: RHEOBYK-431 (manufactured by Pick chemical Co., ltd., japan)
Viscoelasticity modifier A3: RHEOBYK-430 (manufactured by Pick chemical Co., ltd., japan)
Wetting dispersant a: DISPRBYK-2152 (manufactured by Pick chemical Co., ltd.)
PET film, PET substrate: lumirrorS 10 (Dongli Co., ltd.)
Glass substrate: glass square blue plate (sodium) glass (AS ONE company system)
In example a, the curability of the conductive resin composition, the adhesive strength of the conductive film (dry coating film) formed from the conductive resin composition, the volume resistivity, the surface insulation property, and the measurement and evaluation of the LED lighting test were carried out by the following methods.
< Curability >
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and after a coating film of 2cm by 2cm was formed on a glass substrate, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes. The degree of deformation of the coating film was evaluated by the following criteria when the center of the obtained coating film was gently touched with a doctor blade. In the invention, A is qualified, and C is unqualified.
A: the coating film is cured and is not deformed.
C: the coating film is uncured and easily deformed.
< Adhesive Strength >
An epoxy glass substrate (manufactured by Nami Co., ltd.) and 5025 wafer resistance (manufactured by Rohm Co., MCR-50) were prepared, each having copper with an area of 2.0mm 2 etched at 4mm intervals. The conductive resin composition was applied to each electrode terminal of the wafer resistor so as to have an area of 1.5mm 2 and a thickness of 100 μm, and adhered to the copper pattern wiring on the epoxy glass substrate, and the conductive resin composition was cured under a heat treatment condition of 160℃for 60 minutes to prepare a sample for measurement.
For the obtained sample, a wafer shear test (0.1 mm/sec) was performed using Bonding TESTER PTR1102 (manufactured by Rhesca Co.) to determine the adhesive strength.
< Volume resistivity >
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a plastic substrate. Then, the film was heat-cured under heat treatment conditions of 160℃for 60 minutes to prepare a conductive film (dry coating film) having a film thickness as shown in < Table A1 > and < Table A3 > after heat treatment (calcination). The volume resistivity of the conductive film (dry coating film) was measured by a resistivity meter "Loresta GP-MCP T610" (manufactured by Nitto Seiko analysis Co.).
< Surface insulation >)
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a plastic substrate. Then, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes to prepare a conductive film (dry film) having a film thickness as shown in Table A4. The volume resistivity of the conductive film (dry coating film) was measured by a resistivity meter "Loresta GP-MCP T610" (manufactured by Nito Seiko analysis Co., ltd.) and evaluated by the following criteria.
A: surface insulation (volume resistivity of 1.0X10 -1 Ω cm)
C: surface conduction (volume resistivity is lower than 1.0X10 -1. Omega. Cm)
< LED Lighting test >)
An epoxy glass substrate and 5025LED wafer, on which copper having an area of 6.9mm 2 was formed at intervals of 3.8mm by etching, were prepared. After applying a conductive resin composition to an area of 2.5mm 2 and a thickness of 100 μm under each electrode terminal of the LED chip, the conductive resin composition was bonded to the copper pattern wiring on the epoxy glass substrate, and cured under a heat treatment condition of 160 ℃ for 60 minutes to prepare a sample for measurement.
A voltage of 3V electromotive force was applied to both ends of the wiring using an LED tester, and evaluated by the following criteria. In the invention, A is qualified, and C is unqualified.
A: the LED is lit.
C: the LED is not illuminated.
Example A1
15.00 Parts of tin powder A1, 0.84 part of epoxy resin A1, 0.40 part of organic acid compound A1 and 1.00 part of solvent A1 were mixed, and the mixture was stirred using a rotation and revolution stirrer (manufactured by THINKY Co., ltd., "WARIA RING TALang AR-100"), to obtain a conductive resin composition.
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a glass substrate. Then, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes to prepare a conductive film (dry film) having a film thickness as shown in Table A1.
The curability of the obtained conductive resin composition was evaluated.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table A1 >.
Examples A2 to A6 and comparative examples A1 and A2
A conductive resin composition and a conductive film (dry coating film) were produced in the same manner as in example A1, except that the constituent components of the conductive resin composition, the content (parts) thereof, and the film thickness of the conductive film (dry coating film) were each shown in < table A1 >.
The curability of the obtained conductive resin composition was evaluated.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
These results are shown together in < Table A1 >.
The curability of comparative examples A1 and A2 was evaluated as C, and the conductive film (dry coating film) was not formed, and the evaluation and measurement of the film thickness, volume resistivity, LED lighting test, and adhesive strength were not performed.
TABLE 1
< Table A1>
Example A7
1.12 Parts of epoxy resin A1 and 0.38 part of solvent A1 were mixed to obtain a varnish V-A1.
1.50 Parts of varnish V-A1, 15.00 parts of tin powder A1, 0.40 parts of organic acid compound A1 and 1.10 parts of solvent A1 were mixed and stirred using a rotation and revolution stirrer (manufactured by THINKY Co., ltd., "A Zhi Tai Lang AR-100"), to obtain a conductive resin composition.
Using the obtained conductive resin composition, a heat treatment was performed under the conditions described in < table A3 > to produce a conductive film (dry coating film) having a film thickness described in < table A3 > on a glass substrate after the heat treatment.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table A3 >.
Examples A8 to A16
A conductive resin composition and a conductive film (dry film) having film thicknesses as described in < table A3> after heat treatment were produced in the same manner as in example A7, except that the constituent components and the content (parts) thereof of the varnishes V-A4 to V-A9 were as described in < table A2>, and the constituent components, the content (parts) thereof, the base material and the film formation conditions were as described in < table A3>, respectively.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
These results are shown together in < Table A3>.
Examples A17 to A21 and comparative examples A3 and A4
A conductive resin composition and a conductive film (dry coating film) having film thicknesses (dry coating film thicknesses) described in < table A4> were produced in the same manner as in example A7, except that the constituent components and the content (parts) of the varnishes V-A2, V-A3, V-A6, V-a10 and V-a11 were as shown in < table A2>, and the constituent components, the content (parts), the base material and the coating film forming conditions were as shown in < table A4>, respectively.
The curability of the obtained conductive resin composition was evaluated.
The surface insulation properties of the obtained conductive film (dry coating film) were measured.
An LED lighting test was performed using the obtained conductive resin composition.
These results are shown together in < Table A4>.
In comparative example A4, the curability was evaluated as C, and the conductive film (dry coating film) was not formed, and the evaluation and measurement of the film thickness, volume resistivity, LED lighting test, and adhesive strength were not performed.
TABLE 2
< Table A2>
V-A1 | V-A2 | V-A3 | V-A4 | V-A5 | V-A6 | V-A7 | V-A8 | V-A9 | V-A10 | V-A11 | |
Epoxy resin A1 | 1.12 | 1.01 | |||||||||
Epoxy resin A5 | 0.84 | 3.08 | |||||||||
Epoxy resin A6 | 0.84 | 0.84 | |||||||||
Epoxy resin A7 | 0.84 | 2.70 | 0.74 | 0.84 | 2.70 | ||||||
Organic acid Compound A1 | 1.43 | ||||||||||
Organic acid Compound A2 | 0.10 | ||||||||||
Solvent A1 | 0.38 | 1.04 | 0.80 | 3.63 | |||||||
Solvent A3 | 1.70 | 1.00 | |||||||||
Solvent A4 | 1.00 | 3.64 | 1.00 | ||||||||
Solvent A5 | 1.30 | 3.64 |
TABLE 3
Table A3 ]
TABLE 4
< Table A4>
The conductive films (dry coating films) formed from the conductive resin compositions according to examples A1 to a16 each had a volume resistivity of 7.7x -4 Ω·cm or less, and optionally exhibited a conductivity of less than 6.5x -5 Ω·cm equal to or higher than that of silver paste, and were excellent in conductivity. Thus, it is found that a conductive resin composition which is lower in cost than silver paste or the like and which can form a conductive film having high conductivity equivalent to silver paste can be obtained.
The volume resistivity of the conductive films (dry coating films) formed using the conductive resin compositions according to examples a17 to a21 was 1.0×10 -1 Ω·cm or more, the surface insulation was evaluated as a, and the LED lighting test showed satisfactory specific characteristics. As is clear from this, the conductive resin composition of the present invention has a property of exhibiting conductivity inside even if the surface is actually an insulator when forming a film. Further, when the conductive resin composition of the present invention is used to form conductive connection, conductive connection can be formed between connection members, and the film surface is substantially insulating, so that it is known to be useful as a conductive material such as a conductive ink, a conductive adhesive, and a circuit connection material.
Further, as shown in < Table A1 >, the conductive film (dry coating film) formed from the conductive resin composition of the present invention has high adhesion strength and high adhesion to the substrate.
On the other hand, the conductive resin compositions of comparative examples A1 and A2 containing no organic acid compound were evaluated as C in curability, failing to form a conductive film (dry coating film), the conductive resin composition of comparative example A3 using copper powder instead of tin powder was evaluated as C in LED lighting test, failing to exhibit sufficient conductivity, and the conductive resin composition of comparative example A4 using nickel powder instead of tin powder was evaluated as C in curability, failing to form a conductive film (dry coating film).
Example B
Example B is a conductive resin composition according to the present invention, comprising: examples of the conductive resin composition containing the curing agent of (d 1) an acid anhydride-based curing agent and satisfying the requirements of (B) or the conductive resin composition satisfying the requirements of (A) and (B).
The components and substrates used in example B are shown below.
Tin powder B: spherical tin powder (D50=5.5 μm, sn. Gtoreq.99.5% by mass)
Copper powder B: spherical copper powder (particle size 10 μm to 25 μm, manufactured by Sigma-Aldrich Co., ltd., copper powder (spheroidal), 98%)
Nickel powder B: irregularly shaped nickel powder (D90:10 μm or less)
Epoxy resin B1: bisphenol type epoxy resin (jor 1001 manufactured by mitsubishi chemical Co., ltd.)
Epoxy resin B2: bisphenol type epoxy resin (jor 1004 manufactured by mitsubishi chemical Co., ltd.)
Epoxy resin B3: bisphenol type epoxy resin (jor 828 manufactured by Mitsubishi chemical corporation)
Epoxy resin B4: rubber modified epoxy resin (manufactured by ADEKA Co., ltd., EPR-1415-1)
Epoxy resin B5: polysulfide modified epoxy resin (FLEP-50 manufactured by Dongli fine chemical company)
Epoxy resin B6: urethane modified epoxy resin (EPU-73B, manufactured by ADEKA Co., ltd.)
Organic acid compound B1: glutaric acid
Organic acid compound B2: liquid polycarboxylic acid (MMA-10R manufactured by Okamura oil Co., ltd.)
Acid anhydride-based curing agent B1: polyacid polyanhydride (IPU-22 AH, manufactured by Okamura oil Co., ltd.)
Anhydride-based curing agent B2: methyl-5-norbornene-2, 3-dicarboxylic anhydride (KAYAHARD MCD manufactured by Japanese chemical Co., ltd.)
Anhydride-based curing agent B3: succinic anhydride
Anhydride-based curing agent B4: phthalic anhydride
Thiol curing agent B1: multifunctional thiol Compound (TMMP-LV manufactured by SC organic chemical Co., ltd.)
Thiol curing agent B2: multifunctional thiol Compound (PEMP-LV manufactured by SC organic chemical Co., ltd.)
Thiol curing agent B3: multifunctional thiol Compound (DPMP manufactured by SC organic chemical Co., ltd.)
Thiol curing agent B4: multifunctional thiol Compound (TEMPIC, manufactured by SC organic chemistry Co., ltd.)
Thiol curing agent B5: multifunctional thiol Compound (QE-340M manufactured by Dongli Fine chemical Co., ltd.)
Thiol curing agent B6: multifunctional thiol Compound (TS-G, manufactured by four kingdoms chemical industry Co., ltd.)
Thiol curing agent B7: multifunctional thiol Compound (C3 TS-G, manufactured by four chemical industries Co., ltd.)
Thiol curing agent B8: multifunctional thiol Compound (Karenz MT NR-1 manufactured by Zhaowa electric company)
Thiol curing agent B9: multifunctional thiol Compound (LP-3 manufactured by Toli Fine chemical Co., ltd.)
Phenolic curing agent B: liquid phenol resin (MEH-8005, manufactured by Ming He Chemicals Co., ltd.)
Amine curing agent B1: (manufactured by Mitsubishi chemical corporation, ST-11)
Amine curing agent B2: (manufactured by Mitsubishi chemical corporation, ST-14)
Solvent B1: MFDG (dipropylene glycol monomethyl ether)
Solvent B2: ethyl carbitol
Solvent B3: butyl carbitol
PET film, PET substrate: lumirrorS 10 (Dongli Co., ltd.)
Glass substrate: glass square blue plate (sodium) glass (AS ONE company system)
The paste state and curability of the conductive resin composition, the adhesive strength of a conductive film (dry coating film) formed from the conductive resin composition, the volume resistivity, the surface insulation property, and the measurement and evaluation of the LED lighting test were carried out by the following methods.
< Paste State >)
The constituent components and the contents (parts) thereof of the conductive resin composition were set to be < Table B1 > respectively, and the resultant was mixed and stirred using a rotation/revolution stirrer (THINKY Co., ltd., "one-day training Takara AR-100"), to obtain a conductive resin composition. The appearance of the conductive resin composition was visually observed and evaluated by the following criteria. In the invention, A is qualified, and C is unqualified.
A: the conductive resin composition was uniform.
C: agglomeration or the like occurs, and the conductive resin composition is not uniform.
< Curability >
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and after a coating film of 2cm by 2cm was formed on a glass substrate, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes. The degree of deformation of the coating film was evaluated by the following criteria when the center of the obtained coating film was gently touched with a doctor blade. In the invention, A is qualified, and C is unqualified.
A: the coating film is cured and is not deformed.
C: the coating film is uncured and easily deformed.
< Volume resistivity >
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a plastic substrate. Then, the film was heat-cured under heat treatment conditions of 160℃for 60 minutes to prepare a conductive film (dry coating film) having a film thickness as described in < Table B1 > and < Table B4 > after heat treatment (calcination). The volume resistivity of the conductive film (dry coating film) was measured by a resistivity meter "Loresta GP-MCP T610" (manufactured by Nitto Seiko analysis Co.).
< Surface insulation >)
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a plastic substrate. Then, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes to prepare a conductive film (dry coating film) having a film thickness as described in < Table B2 >, < Table B5 > and < Table B6 >. The volume resistivity of the conductive film (dry coating film) was measured by a resistivity meter "Loresta GP-MCP T610" (manufactured by Nito Seiko analysis Co., ltd.) and evaluated by the following criteria.
A: surface insulation (volume resistivity of 1.0X10 -1 Ω cm)
C: surface conduction (volume resistivity is lower than 1.0X10 -1. Omega. Cm)
< LED Lighting test >)
An epoxy glass substrate and 5025LED wafer, on which copper having an area of 6.9mm 2 was formed at intervals of 3.8mm by etching, were prepared. After applying a conductive resin composition to an area of 2.5mm 2 and a thickness of 100 μm under each electrode terminal of the LED chip, the conductive resin composition was bonded to the copper pattern wiring on the epoxy glass substrate, and cured under a heat treatment condition of 160 ℃ for 60 minutes to prepare a sample for measurement.
A voltage of 3V electromotive force was applied to both ends of the wiring using an LED tester, and evaluated by the following criteria. In the invention, A is qualified, and C is unqualified.
A: the LED is lit.
C: the LED is not illuminated.
< Adhesive Strength >
An epoxy glass substrate (manufactured by Nami Co., ltd.) and 5025 wafer resistance (manufactured by Rohm Co., MCR-50) were prepared, each having copper with an area of 2.0mm 2 etched at 4mm intervals. The conductive resin composition was applied to each electrode terminal of the wafer resistor so as to have an area of 1.5mm 2 and a thickness of 100 μm, and adhered to the copper pattern wiring on the epoxy glass substrate, and the conductive resin composition was cured under a heat treatment condition of 160℃for 60 minutes to prepare a sample for measurement.
For the obtained sample, a wafer shear test (0.1 mm/sec) was performed using Bonding TESTER PTR1102 (manufactured by Rhesca Co.) to determine the adhesive strength.
Example B1
15.00 Parts of tin powder B, 0.52 part of epoxy resin B1, 0.40 part of organic acid compound B1, 0.32 part of acid anhydride-based curing agent B1 and 1.00 parts of solvent B1 were mixed and stirred using a rotation and revolution stirrer (THINKY Co., ltd., "Koshi Lishi AR-100") to obtain a conductive resin composition.
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a glass substrate. Then, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes to prepare a conductive film (dry film) having a film thickness as shown in Table B1.
The paste state and curability of the obtained conductive resin composition were evaluated.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table B1 >.
Examples B2 to B10 and comparative examples B1 to B4
A conductive resin composition and a conductive film (dry coating film) were produced in the same manner as in example B1, except that the constituent components of the conductive resin composition, the content (parts) thereof, and the film thickness of the conductive film (dry coating film) were each shown in < table B1 >.
The paste state and curability of the obtained conductive resin composition were evaluated.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table B1 >.
In comparative examples B1 and B2, the paste state was a, but the curability was evaluated as C, and the conductive film (dry coating film) was not formed, and the evaluation and measurement of the adhesive strength, film thickness, and volume resistivity were not performed. In comparative examples B3 and B4, the conductive resin composition was not uniform in the paste state C, and evaluation and measurement of curability, adhesive strength, film thickness, and volume resistivity were not performed.
TABLE 5
< Table B1>
Examples B11 to B21
A conductive resin composition and a conductive film (dry coating film) were produced in the same manner as in example B1, except that the constituent components of the conductive resin composition, the content (parts) thereof, and the film thickness of the conductive film (dry coating film) were each shown in < table B2 >.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dry coating film) were measured.
These results are shown together in < Table B2 >.
TABLE 6
< Table B2>
Example B22
10.00 Parts of epoxy resin B6 and 11.84 parts of anhydride curing agent B1 are mixed to obtain varnish V-B1.
A conductive resin composition was obtained by mixing and stirring 0.84 parts of varnish V-B1, 15.00 parts of tin powder B, 0.40 parts of an organic acid compound B1 and 1.50 parts of a solvent B1 using a rotation and revolution stirrer (manufactured by THINKY Co., ltd., "Washi Zhi Takara Shuzo AR-100").
Using the obtained conductive resin composition, a heat treatment was performed under the conditions described in < table B4 > to produce a conductive film (dry coating film) having a film thickness described in < table B4 > on a glass substrate after the heat treatment.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The adhesive strength was measured using the obtained conductive resin composition.
These results are shown together in < Table B4 >.
Examples B23 to B25
A conductive resin composition and a conductive film (dry coating film) having film thicknesses (dry coating film thicknesses) as described in < table B4 > were produced in the same manner as in example B22, except that the constituent components and the content (parts) thereof of the varnishes V-B2 to V-B4 were set to < table B3 > and the constituent components, the content (parts) thereof, and the coating film formation conditions were set to < table B4 > respectively.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The adhesive strength was measured using the obtained conductive resin composition.
These results are shown together in < Table B4 >.
TABLE 7
< Table B3>
V-B1 | V-B2 | V-B3 | V-B4 | V-B5 | V-B6 | V-B7 | V-B8 | |
Epoxy resin B3 | 2.00 | 2.00 | 2.00 | 2.00 | 4.70 | 3.20 | ||
Epoxy resin B4 | 15.00 | |||||||
Epoxy resin B6 | 10.00 | |||||||
Organic acid Compound B1 | 1.82 | 1.82 | 1.82 | 1.82 | 2.00 | |||
Anhydride curing agent B1 | 11.84 | 10.88 | 0.91 | 1.21 | 0.61 | 0.45 | 1.47 | 1.00 |
Thiol curing agent B1 | 0.61 | 0.61 | 0.45 | |||||
Phenolic curing agent B | 0.91 | 0.61 | 0.91 | |||||
Solvent B1 | 2.50 | 2.50 | ||||||
Solvent B2 | 4.55 | 4.55 | ||||||
Solvent B3 | 4.55 | 4.55 |
TABLE 8
< Table B4>
Examples B26 to B28
A conductive resin composition and a conductive film (dry coating film) having film thicknesses (dry coating film thicknesses) described in < table B5> were produced in the same manner as in example B22 except that the constituent components and the content (parts) thereof of the varnishes V-B2, V-B5 and V-B6 were shown in < table B3>, and the constituent components, the content (parts) thereof and the coating film formation conditions were shown in < table B5 >.
The surface insulation properties of the obtained conductive film (dry coating film) were measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table B5>.
TABLE 9
< Table B5>
Comparative examples B5 to B7
A conductive resin composition and a conductive film (dry coating film) having a film thickness (dry coating film thickness) as described in < table B6 > were produced in the same manner as in example B22 except that the constituent components and the content (parts) thereof of the varnishes V-B7 and V-B8 were shown in < table B3 > and the constituent components, the content (parts) thereof and the coating film forming conditions were shown in < table B6 >.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table B6 >.
In comparative examples B5 and B7, since the curability was evaluated as C and the conductive film (dry coating film) was not formed, the evaluation and measurement of the film thickness, the adhesive strength, the volume resistivity, and the LED lighting test were not performed.
TABLE 10
< Table B6>
The conductive films (dry coating films) formed from the conductive resin compositions according to examples B1 to B10 and B22 to B25 each had a volume resistivity of less than 1.0x -3 Ω·cm, and optionally had conductivity of less than 1.0x -4 Ω·cm equal to or higher than that of silver paste, and were excellent in conductivity. Thus, it is found that a conductive resin composition which is lower in cost than silver paste or the like and which can form a conductive film having high conductivity equivalent to silver paste can be obtained.
The volume resistivity of the conductive films (dry coating films) formed using the conductive resin compositions according to examples B11 to B21 and B26 to B28 was 1.0×10 -1 Ω·cm or more, the surface insulation property was evaluated as a, and the LED lighting test showed satisfactory specific characteristics. As is clear from this, the conductive resin composition of the present invention has a property of exhibiting conductivity inside even if the surface is actually an insulator when forming a film. Further, when the conductive resin composition of the present invention is used to form conductive connection, conductive connection can be formed between connection members, and the film surface is substantially insulating, so that it is known to be useful as a conductive material such as a conductive ink, a conductive adhesive, and a circuit connection material.
Further, as shown in < Table B1 >, < Table B2 >, < Table B4 > and < Table B5 >, it is clear that the conductive film (dry coating film) formed by the conductive resin composition of the present invention has a strong adhesive strength and a high adhesion to the substrate.
On the other hand, the conductive resin compositions of comparative examples B1, B2, and B5 containing no organic acid compound were evaluated for curability as C, failing to form a conductive film (dry coating film), the conductive resin compositions of comparative examples B3 and B4 containing an amine-based curing agent instead of an acid anhydride-based curing agent were evaluated for curability as C, and the conductive resin compositions of comparative example B6 containing a copper powder instead of tin powder were evaluated for LED lighting test as C, failing to form a conductive film (dry coating film), and the conductive resin compositions of comparative example B7 containing a nickel powder instead of tin powder were evaluated for curability as C.
Example C
Example C is a conductive resin composition according to the present invention, comprising: examples of the conductive resin composition containing (d 2) a thiol-based curing agent and satisfying the requirements of (B) or the conductive resin composition satisfying the requirements of (A) and (B).
The components and substrates used in example C are shown below.
Tin powder C: spherical tin powder (D50=5.5 μm, sn. Gtoreq.99.5% by mass)
Copper powder C: spherical copper powder (particle size 10 μm to 25 μm, manufactured by Sigma-Aldrich Co., ltd., copper powder (spheroidal), 98%)
Epoxy resin C1: bisphenol type epoxy resin (jor 828 manufactured by Mitsubishi chemical corporation)
Epoxy resin C2: bisphenol type epoxy resin (jor 1001 manufactured by mitsubishi chemical Co., ltd.)
Epoxy resin C3: bisphenol type epoxy resin (jor 1004 manufactured by mitsubishi chemical Co., ltd.)
Epoxy resin C4: strong toughness epoxy resin (LCE-2615, manufactured by Japanese chemical Co., ltd.)
Epoxy resin C5: urethane modified epoxy resin (EPU-73B, manufactured by ADEKA Co., ltd.)
Epoxy resin C6: rubber modified epoxy resin (manufactured by ADEKA Co., ltd., EPR-1415-1)
Epoxy resin C7: polysulfide modified epoxy resin (FLEP-50 manufactured by Dongli fine chemical company)
Organic acid compound C1: glutaric acid
Organic acid compound C2: liquid polycarboxylic acid (MMA-10R manufactured by Okamura oil Co., ltd.)
Thiol curing agent C1: multifunctional thiol Compound (TMMP-LV manufactured by SC organic chemical Co., ltd.)
Thiol curing agent C2: multifunctional thiol Compound (PEMP-LV manufactured by SC organic chemical Co., ltd.)
Thiol curing agent C3: multifunctional thiol Compound (DPMP manufactured by SC organic chemical Co., ltd.)
Thiol curing agent C4: multifunctional thiol Compound (TEMPIC, manufactured by SC organic chemistry Co., ltd.)
Thiol curing agent C5: multifunctional thiol Compound (QE-340M manufactured by Dongli Fine chemical Co., ltd.)
Thiol curing agent C6: multifunctional thiol Compound (TS-G, manufactured by four kingdoms chemical industry Co., ltd.)
Thiol curing agent C7: multifunctional thiol Compound (C3 TS-G, manufactured by four chemical industries Co., ltd.)
Thiol curing agent C8: multifunctional thiol Compound (Karenz MT NR-1 manufactured by Zhaowa electric company)
Thiol curing agent C9: multifunctional thiol Compound (LP-3 manufactured by Toli Fine chemical Co., ltd.)
Thiol curing agent C10: multifunctional thiol Compound (LP-2 manufactured by Toli Fine chemical Co., ltd.)
Thiol curing agent C11: multifunctional thiol Compound (LP-31 manufactured by Toli Fine chemical Co., ltd.)
Thiol curing agent C12: multifunctional thiol Compound (manufactured by Toli Fine chemical Co., ltd., LP-55)
Anhydride-based curing agent C: polyacid polyanhydride (IPU-22 AH, manufactured by Okamura oil Co., ltd.)
Phenolic hardener C: liquid phenol resin (MEH-8005, manufactured by Ming He Chemicals Co., ltd.)
Amine curing agent C1: (manufactured by Mitsubishi chemical corporation, ST-11)
Amine curing agent C2: (manufactured by Mitsubishi chemical corporation, ST-14)
Solvent C1: MFDG (dipropylene glycol monomethyl ether)
Solvent C2: butyl carbitol
Solvent C3: ethyl carbitol
Antioxidant C1: hindered phenol compound (Irganox 1010, manufactured by BASF corporation)
Antioxidant C2: hindered phenol compounds (Nonflex EBP manufactured by Seiko chemical Co., ltd.)
Antioxidant C3: hindered phenol compounds (Nonflex CBP manufactured by Seiko chemical Co., ltd.)
Antioxidant C4: hindered phenols (ADK STAB AO-50, manufactured by ADEKA Co., ltd.)
Antioxidant C5: hindered phenols (ADK STAB AO-80, manufactured by ADEKA Co., ltd.)
Antioxidant C6: hydroquinone
Heavy metal passivating agent C1: ADK STAB CDA-6S manufactured by ADEKA Co
Heavy metal passivating agent C2: ADK STAB ZS-90 manufactured by ADEKA Co
Heavy metal passivating agent C3: ADK STAB ZS-27 manufactured by ADEKA Co
Cure accelerator C1: guanidine compounds (SANCELER D manufactured by Sanxinshi chemical industry Co., ltd.)
Cure accelerator C2: guanidine compounds (SANCELER DT manufactured by Sanxinshi chemical industry Co., ltd.)
PET film, PET substrate: lumirrorS 10 (Dongli Co., ltd.)
Glass substrate: glass square blue plate (sodium) glass (AS ONE company system)
The paste state and curability of the conductive resin composition, the adhesive strength of the conductive film (dry coating film) formed from the conductive resin composition, the surface insulation property, the volume resistivity, and the measurement and evaluation of the LED lighting test were carried out by the following methods.
< Paste State >)
The constituent components and the contents (parts) thereof of the conductive resin composition were set to be < Table C1 > respectively, and the resultant was mixed and stirred using a rotation/revolution stirrer (THINKY Co., ltd., "one-day training Takara AR-100"), to obtain a conductive resin composition. The appearance of the conductive resin composition was visually observed and evaluated by the following criteria. In the invention, A is qualified, and C is unqualified.
A: the conductive resin composition was uniform.
C: agglomeration or the like occurs, and the conductive resin composition is not uniform.
< Curability >
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and after a coating film of 2cm by 2cm was formed on a glass substrate, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes. The degree of deformation of the coating film was evaluated by the following criteria when the center of the obtained coating film was gently touched with a doctor blade. In the invention, A is qualified, and C is unqualified.
A: the coating film is cured and is not deformed.
C: the coating film is uncured and easily deformed.
< Volume resistivity >
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a plastic substrate. Then, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes to prepare a conductive film (dried film) having a film thickness as shown in Table C6. The volume resistivity of the conductive film (dry coating film) was measured by a resistivity meter "Loresta GP-MCP T610" (manufactured by Nitto Seiko analysis Co.).
< Surface insulation >)
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a plastic substrate. Then, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes to prepare a conductive film (dry coating film) having a film thickness of 100 μm or less as shown in Table C5. The volume resistivity of the conductive film (dry coating film) was measured by a resistivity meter "Loresta GP-MCP T610" (manufactured by Nito Seiko analysis Co., ltd.) and evaluated by the following criteria.
A: surface insulation (volume resistivity of 1.0X10 -1 Ω cm)
C: surface conduction (volume resistivity is lower than 1.0X10 -1. Omega. Cm)
< LED Lighting test >)
An epoxy glass substrate and 5025LED wafer, on which copper having an area of 6.9mm 2 was formed at intervals of 3.8mm by etching, were prepared. After applying a conductive resin composition under each electrode terminal of the LED chip so as to have an area of 2.5mm 2, the conductive resin composition was bonded to the copper pattern wiring on the epoxy glass substrate, and the conductive resin composition was cured under a heat treatment condition of 160 ℃ for 60 minutes to prepare a sample for measurement.
A voltage of 3V electromotive force was applied to both ends of the wiring using an LED tester, and evaluated by the following criteria. In the invention, A is qualified, and C is unqualified.
A: the LED is lit.
C: the LED is not illuminated.
< Adhesive Strength >
An epoxy glass substrate (manufactured by Nami Co., ltd.) and 5025 wafer resistance (manufactured by Rohm Co., MCR-50) were prepared, each having copper with an area of 2.0mm 2 etched at 4mm intervals. The conductive resin composition was applied to each electrode terminal of the wafer resistor so as to have an area of 1.5mm 2 and a thickness of 100 μm, and adhered to the copper pattern wiring on the epoxy glass substrate, and the conductive resin composition was cured under a heat treatment condition of 160℃for 60 minutes to prepare a sample for measurement.
For the obtained sample, a wafer shear test (0.1 mm/sec) was performed using Bonding TESTER PTR1102 (manufactured by Rhesca Co.) to determine the adhesive strength.
Example C1
15.00 Parts of tin powder C, 0.48 part of epoxy resin C1, 0.40 part of organic acid compound C1, 0.36 part of thiol curing agent C1 and 1.00 parts of solvent C1 are mixed and stirred by using a rotation and revolution stirrer (THINKY Co., ltd., "Koshi mountain Telang AR-100") to obtain a conductive resin composition.
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a glass substrate. Then, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes to prepare a conductive film (dry coating film) having a film thickness of 100. Mu.m.
The paste state and curability of the obtained conductive resin composition were evaluated.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dry coating film) were measured.
These results are shown together in < Table C1 >.
Examples C2 to C22 and comparative examples C1 to C4
A conductive resin composition and a conductive film (dry coating film) were produced in the same manner as in example C1, except that the constituent components of the conductive resin composition and the content (parts) thereof were as shown in < table C1 > to < table C3 >, respectively.
The paste state and curability of the obtained conductive resin composition were evaluated.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dry coating film) were measured.
These results are shown together in < Table C1 > - < Table C3 >.
In comparative example C1, the paste state was a, but the curability was evaluated as C, and the conductive film (dry coating film) was not formed, and the evaluation and measurement of the adhesive strength, the surface insulation property, and the LED lighting test were not performed. In comparative examples C2 and C3, the conductive resin composition was not uniform in the paste state C, and evaluation and measurement of curability, adhesive strength, surface insulation, and LED lighting test were not performed.
TABLE 11
< Table C1>
TABLE 12
< Table C2>
TABLE 13
< Table C3>
Example C23
2.00 Parts of an epoxy resin C1, 1.82 parts of an organic acid compound C1, 0.91 part of a thiol curing agent C1, 0.91 part of a phenol curing agent C and 4.55 parts of a solvent C3 were mixed to obtain a varnish V-C1.
2.24 Parts of varnish V-C1 and 15.00 parts of tin powder C were mixed, and the mixture was stirred using a rotation/revolution stirrer (THINKY Co., ltd., "A-Lily Talang AR-100") to obtain a conductive resin composition.
Using the obtained conductive resin composition, a conductive film (dry coating film) having a film thickness described in < table C5> after heat treatment was produced in the same manner as in example C1.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dry coating film) were measured.
These results are shown together in < Table C5>.
Examples C24 to C33
A conductive resin composition and a conductive film (dry coating film) having a film thickness as described in < table C5> after heat treatment were produced in the same manner as in example C23, except that the constituent components and the content (parts) of the varnishes V-C1 to V-C10 were shown in < table C4>, and the constituent components and the content (parts) of the conductive resin composition were shown in < table C5 >.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dry coating film) were measured.
These results are shown together in < Table C5>.
Examples C34 to C37
A conductive resin composition and a conductive film (dry coating film) having a film thickness as described in < table C6> after heat treatment were produced in the same manner as in example C23, except that the constituent components and the content (parts) of the varnishes V-C8, V-C10 and V-C12 were as shown in < table C4>, and the constituent components and the content (parts) thereof of the conductive resin composition were as shown in < table C6 >.
The adhesive strength was measured using the obtained conductive resin composition.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
These results are shown together in < Table C6>.
TABLE 14
< Table C4>
V-C1 | V-C2 | V-C3 | V-C4 | V-C5 | V-C6 | V-C7 | V-C8 | V-C9 | V-C10 | V-C11 | V-C12 | |
Epoxy resin C1 | 2.00 | 2.00 | 2.00 | 2.00 | 2.40 | |||||||
Epoxy resin C2 | 3.75 | 3.75 | 3.75 | 3.75 | 3.75 | 3.75 | 8.25 | |||||
Organic acid Compound C1 | 1.82 | 1.82 | 1.82 | 1.82 | 2.29 | 1.14 | 1.08 | 1.02 | 1.91 | 0.96 | 2.24 | 2.00 |
Organic acid Compound C2 | 1.14 | 1.08 | 1.02 | 0.96 | 2.24 | |||||||
Thiol curing agent C1 | 0.91 | 0.61 | 0.61 | 0.45 | 1.05 | 1.05 | 0.79 | 0.53 | 0.26 | 0.26 | 1.16 | 1.80 |
Acid anhydride curing agent C | 0.61 | 0.45 | ||||||||||
Phenolic curing agent C | 0.91 | 0.61 | 1.21 | 0.91 | ||||||||
Solvent C1 | 2.50 | |||||||||||
Solvent C2 | 5.70 | 2.85 | 2.73 | 2.55 | 4.75 | 2.37 | 5.61 | |||||
Solvent C3 | 4.55 | 4.55 | 4.55 | 4.55 |
TABLE 15
< Table C5>
TABLE 16
< Table C6>
/>
Examples C38 to C49
A conductive resin composition and a conductive film (dry coating film) were produced in the same manner as in example C23, except that the constituent components and the content (parts) thereof of the varnish V-C11 were shown in < table C4 > and the constituent components and the content (parts) thereof of the conductive resin composition were shown in < table C7 > and the film thickness after heat treatment was 100 μm.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
The surface insulation properties of the obtained conductive film (dry coating film) were measured.
These results are shown together in < Table C7 >.
TABLE 17
< Table C7>
The volume resistivity of the conductive films (dry coating films) formed from the conductive resin compositions according to examples C1 to C33 and C38 to C49 was 1.0x -1 Ω·cm or more, the surface insulation property was evaluated as a, and the LED lighting test showed satisfactory specific characteristics. As is clear from this, the conductive resin composition of the present invention has a property of exhibiting conductivity inside even if the surface is actually an insulator when forming a film. Further, when the conductive resin composition of the present invention is used to form conductive connection, conductive connection can be formed between connection members, and the film surface is substantially insulating, so that it is known to be useful as a conductive material such as a conductive ink, a conductive adhesive, and a circuit connection material.
The conductive films (dry coating films) formed from the conductive resin compositions according to examples C34 to C37 each had a volume resistivity of 1.2x -4 Ω·cm or less (on the order of 10 -5 Ω·cm in examples C34 to C36) and were excellent in conductivity, which was equal to or higher than that of silver paste. Thus, it is found that a conductive resin composition which is lower in cost than silver paste or the like and which can form a conductive film having high conductivity equivalent to silver paste can be obtained.
Further, as shown in < Table C1 > - < Table C3 > - < Table C5 > - < Table C7 >, it is clear that the conductive film (dry coating film) formed by the conductive resin composition of the present invention has a strong adhesive strength and a high adhesion to the substrate. In particular, examples C28 to C30, C32 to C36, and C38 to C49, in which 2 kinds of organic acid compounds were used in combination, exhibited high adhesive strength.
On the other hand, the conductive resin composition of comparative example C1 containing no organic acid compound was evaluated as C in curability, failed to form a conductive film (dry coating film), the conductive resin composition of comparative examples C2 and C3 using an amine curing agent instead of a thiol curing agent was in a paste state of C, and caking occurred, failing to produce a uniform conductive resin composition, and the conductive resin composition of comparative example C4 using a copper powder instead of tin powder was evaluated as C in LED lighting test, and did not exhibit sufficient conductivity.
Example D
Example D is a conductive resin composition according to the present invention, comprising: examples of the conductive resin composition containing (d 3) a phenolic curing agent and satisfying the requirements of (B) or the conductive resin composition satisfying the requirements of (A) and (B).
The components and substrates used in example D are shown below.
Tin powder D1: spherical tin powder (D50=5.5 μm, sn. Gtoreq.99.5% by mass)
Tin powder D2: irregularly shaped tin powder (d50=7.5 μm, sn+.99.9 mass%)
Copper powder D: spherical copper powder (particle size 10 μm to 25 μm, manufactured by Sigma-Aldrich Co., ltd., copper powder (spheroidal), 98%)
Nickel powder D: irregularly shaped nickel powder (D90:10 μm or less)
Epoxy resin D1: bisphenol type epoxy resin (jor 1001 manufactured by mitsubishi chemical Co., ltd.)
Epoxy resin D2: urethane modified epoxy resin (EPU-73B, manufactured by ADEKA Co., ltd.)
Epoxy resin D3: bisphenol type epoxy resin (jor 828 manufactured by Mitsubishi chemical corporation)
Epoxy resin D4: rubber modified epoxy resin (manufactured by ADEKA Co., ltd., EPR-1415-1)
Organic acid compound D1: glutaric acid
Organic acid compound D2: pimelic acid
Organic acid compound D3: azelaic acid
Organic acid compound D4: diethylene glycol acid
Organic acid compound D5: succinic acid
Organic acid compound D6: adipic acid
Phenolic hardener D1: liquid phenol resin (MEH-8005, manufactured by Ming He Chemicals Co., ltd.)
Phenolic hardener D2: biphenylaralkyl phenol resin (KAYA HARD GPH-103 manufactured by Japanese chemical Co., ltd.)
Phenolic hardener D3: biphenylaralkyl phenol resin (KAYA HARD GPH-65 manufactured by Japanese chemical Co., ltd.)
Amine curing agent D1: (manufactured by Mitsubishi chemical corporation, ST-11)
Amine curing agent D2: (manufactured by Mitsubishi chemical corporation, ST-14)
Solvent D1: MFDG (dipropylene glycol monomethyl ether)
Solvent D2: butyl carbitol
Solvent D3: ethyl carbitol
PET film, PET substrate: lumirrorS 10 (Dongli Co., ltd.)
Glass substrate: glass square blue plate (sodium) glass (AS ONE company system)
The paste state and curability of the conductive resin composition, the volume resistivity of the conductive film (dry coating film) formed by the conductive resin composition, the surface insulation property, the adhesive strength, and the measurement and evaluation of the LED lighting test were carried out by the following methods.
< Paste State >)
The constituent components and the contents (parts) thereof of the conductive resin composition were set to be < Table D1 > respectively, and the resultant was mixed and stirred using a rotation/revolution stirrer (THINKY Co., ltd., "one-day training Takara AR-100"), to obtain a conductive resin composition. The appearance of the conductive resin composition was visually observed and evaluated by the following criteria. In the invention, A is qualified, and C is unqualified.
A: the conductive resin composition was uniform.
C: agglomeration or the like occurs, and the conductive resin composition is not uniform.
< Curability >
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and after a coating film of 2cm by 2cm was formed on a glass substrate, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes. The degree of deformation of the coating film was evaluated by the following criteria when the center of the obtained coating film was gently touched with a doctor blade. In the invention, A is qualified, and C is unqualified.
A: the coating film is cured and is not deformed.
C: the coating film is uncured and easily deformed.
< Volume resistivity >
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a plastic substrate. Then, the film was heat-cured under heat treatment conditions of 160℃for 60 minutes to prepare a conductive film (dry coating film) having a film thickness as shown in the following tables D1 and D3. The volume resistivity of the conductive film (dry coating film) was measured by a resistivity meter "Loresta GP-MCP T610" (manufactured by Nitto Seiko analysis Co.).
< Surface insulation >)
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a plastic substrate. Then, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes to prepare a conductive film (dry film) having a film thickness as shown in Table D4. The volume resistivity of the conductive film (dry coating film) was measured by a resistivity meter "Loresta GP-MCP T610" (manufactured by Nito Seiko analysis Co., ltd.) and evaluated by the following criteria.
A: surface insulation (volume resistivity of 1.0X10 -1 Ω cm)
C: surface conduction (volume resistivity is lower than 1.0X10 -1. Omega. Cm)
< LED Lighting test >)
An epoxy glass substrate and 5025LED wafer, on which copper having an area of 6.9mm 2 was formed at intervals of 3.8mm by etching, were prepared. After applying a conductive resin composition to an area of 2.5mm 2 and a thickness of 100 μm under each electrode terminal of the LED chip, the conductive resin composition was bonded to the copper pattern wiring on the epoxy glass substrate, and cured under a heat treatment condition of 160 ℃ for 60 minutes to prepare a sample for measurement.
A voltage of 3V electromotive force was applied to both ends of the wiring using an LED tester, and evaluated by the following criteria. In the invention, A is qualified, and C is unqualified.
A: the LED is lit.
C: the LED is not illuminated.
< Adhesive Strength >
An epoxy glass substrate (manufactured by Nami Co., ltd.) and 5025 wafer resistance (manufactured by Rohm Co., MCR-50) were prepared, each having copper with an area of 2.0mm 2 etched at 4mm intervals. The conductive resin composition was applied to each electrode terminal of the wafer resistor so as to have an area of 1.5mm 2 and a thickness of 100 μm, and adhered to the copper pattern wiring on the epoxy glass substrate, and the conductive resin composition was cured under a heat treatment condition of 160℃for 60 minutes to prepare a sample for measurement.
For the obtained sample, a wafer shear test (0.1 mm/sec) was performed using Bonding TESTER PTR1102 (manufactured by Rhesca Co.) to determine the adhesive strength.
Example D1
15.00 Parts of tin powder D1, 0.65 part of epoxy resin D1, 0.40 part of organic acid compound D1, 0.19 part of phenolic curing agent D1 and 1.00 parts of solvent D1 were mixed and stirred using a rotation and revolution stirrer (THINKY Co., ltd., "Koshi mountain sea mountain AR-100") to obtain a conductive resin composition.
The conductive resin composition was printed by hand using a PET film having holes of 2cm by 2cm as a mask, and a coating film of 2cm by 2cm was formed on a glass substrate. Then, the film was heat-cured under a heat treatment condition of 160℃for 60 minutes to prepare a conductive film (dry film) having a film thickness as shown in Table D1.
The paste state and curability of the obtained conductive resin composition were evaluated.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table D1 >.
Examples D2 to D10 and comparative examples D1 to D3
A conductive resin composition and a conductive film (dry coating film) were produced in the same manner as in example D1, except that the constituent components of the conductive resin composition, the content (parts) thereof, and the film thickness of the conductive film (dry coating film) were each shown in < table D1 >.
The paste state and curability of the obtained conductive resin composition were evaluated.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table D1 >.
In example D10, the volume resistivity was 1.0x -1 Ω·cm or more, and the surface insulation was determined, but the evaluation of the LED lighting test was a (LED lighting).
In comparative example D1, the paste state was a, but the curability was evaluated as C, and the conductive film (dry coating film) was not formed, and the evaluation and measurement of the film thickness, the volume resistivity, the LED lighting test, and the adhesive strength were not performed. In comparative examples D2 and D3, the paste state was C, and the conductive resin composition was not uniform, and thus the curability, the film thickness, the volume resistivity, the LED lighting test, and the evaluation and measurement of the adhesive strength were not performed.
TABLE 18
< Table D1>
Example D11
10.00 Parts of epoxy resin D2 and 5.50 parts of phenolic curing agent D1 were mixed to obtain a varnish V-D1.
A conductive resin composition was obtained by mixing 0.84 part of varnish V-D1, 15.00 parts of tin powder D1, 0.40 part of organic acid compound D1 and 1.50 parts of solvent D1, and stirring the mixture using a rotation and revolution stirrer (THINKY Co., ltd., "A. Zhi Tailang AR-100").
Using the obtained conductive resin composition, a conductive film (dry coating film) having a film thickness (dry coating film thickness) as described in < table D3 > was produced in the same manner as in example D1.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table D3>.
Examples D12 to D20 and comparative examples D4 and D5
A conductive resin composition and a conductive film (dry coating film) having a film thickness as described in < table D3> after heat treatment were produced in the same manner as in example D11, except that the constituent components and the content (parts) of the varnishes V-D1 to V-D11 were shown in < table D2> and the constituent components and the content (parts) of the conductive resin composition were shown in < table D3 >.
The volume resistivity of the obtained conductive film (dry coating film) was measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table D3>.
TABLE 19
< Table D2>
V-D1 | V-D2 | V-D3 | V-D4 | V-D5 | V-D6 | V-D7 | V-D8 | V-D9 | V-D10 | V-D11 | |
Epoxy resin D2 | 10.00 | ||||||||||
Epoxy resin D3 | 3.00 | 3.00 | 3.00 | 3.00 | 3.00 | 3.00 | 2.45 | 2.45 | 1.94 | ||
Epoxy resin D4 | 8.20 | ||||||||||
Phenolic curing agent D1 | 5.50 | 2.13 | 2.13 | 2.13 | 2.13 | 3.37 | 2.13 | 2.13 | 1.75 | 1.75 | 1.45 |
Organic acid compound D1 | 2.44 | 2.00 | 1.58 | ||||||||
Organic acid compound D2 | 2.44 | 2.00 | |||||||||
Organic acid compound D3 | 2.44 | ||||||||||
Organic acid Compound D4 | 2.44 | ||||||||||
Organic acid Compound D5 | 2.44 | ||||||||||
Organic acid Compound D6 | 2.44 | ||||||||||
Solvent D1 | 2.50 | ||||||||||
Solvent D3 | 6.11 | 6.11 | 6.11 | 6.11 | 6.11 | 6.11 | 2.50 | 4.00 |
TABLE 20
< Table D3>
/>
Examples D21 to D25
A conductive resin composition and a conductive film (dry coating film) having a film thickness (film thickness of dry coating film) described in < table D4> were produced in the same manner as in example D11, except that the constituent components and contents (parts) of the varnish were shown in < table D2> and the constituent components and contents (parts) of the conductive resin composition were shown in < table D4 >.
The surface insulation properties of the obtained conductive film (dry coating film) were measured.
The LED lighting test and the adhesive strength measurement were performed using the obtained conductive resin composition.
These results are shown together in < Table D4 >.
TABLE 21
< Table D4>
The conductive films (dry coating films) formed from the conductive resin compositions according to examples D1 to D9 and D11 to D20 each had a volume resistivity of less than 1.0x -3 Ω·cm, and optionally had conductivity of less than 1.0x -4 Ω·cm equal to or higher than that of silver paste, and were excellent in conductivity. Thus, it is found that a conductive resin composition which is lower in cost than silver paste or the like and which can form a conductive film having high conductivity equivalent to silver paste can be obtained.
The volume resistivity of the conductive films (dry coating films) formed using the conductive resin compositions according to examples D10 and D21 to D25 was 1.0×10 -1 Ω·cm or more, the surface insulation was a, and the LED lighting test showed satisfactory specific characteristics. As is clear from this, the conductive resin composition of the present invention has a property of exhibiting conductivity inside even if the surface is actually an insulator when forming a film. Further, when the conductive resin composition of the present invention is used to form conductive connection, conductive connection can be formed between connection members, and the film surface is substantially insulating, so that it is known to be useful as a conductive material such as a conductive ink, a conductive adhesive, and a circuit connection material.
Further, as shown in < Table D1 >, < Table D3 > and < Table D4 >, it is clear that the conductive film (dry coating film) formed by the conductive resin composition of the present invention has a strong adhesive strength and a high adhesion to the substrate.
On the other hand, the conductive resin composition of comparative example D1 containing no organic acid compound was evaluated as C in curability, and a conductive film (dry coating film) was not formed, and the conductive resin compositions of comparative examples D2 and D3 using an amine-based curing agent instead of a phenol-based curing agent had a paste state of C, and were agglomerated to produce a uniform conductive resin composition, and the conductive resin composition of comparative example D4 using a copper powder instead of a tin powder and the conductive resin composition of comparative example D5 using a nickel powder instead of a tin powder were evaluated as C in LED lighting test, and did not exhibit sufficient conductivity.
Claims (8)
1. A conductive resin composition which contains (a) tin powder, (B) an epoxy resin and (c) an organic acid compound and satisfies the following requirements (A) and/or (B):
(A) : the content of the tin powder (a) in the total amount of 100 mass% of the tin powder (a), the epoxy resin (b) and the organic acid compound (c) is 90.1 mass% or more,
(B) : the resin composition contains (d) a curing agent, wherein the (d) curing agent contains (d 1) an acid anhydride curing agent, (d 2) a thiol curing agent and (d 3) at least 1 phenolic curing agent.
2. The electroconductive resin composition according to claim 1, wherein the (b) epoxy resin satisfies the following requirements (i) and/or (ii):
(i) : is in a liquid state at the temperature of 25 ℃,
(Ii) : is at least 1 selected from 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, triphenol methane type epoxy resin, naphthalene type epoxy resin, dicyclopentadiene modified epoxy resin, aliphatic epoxy resin, polyether modified epoxy resin, polyfunctional aromatic epoxy resin and hydrogenated bisphenol type epoxy resin.
3. The conductive resin composition according to claim 1 or 2, wherein the (d 1) acid anhydride-based curing agent is a polyacid polyanhydride represented by the following structural formula (1);
[ chemical formula 1]
In the structural formula (1), R 1 is a straight-chain or branched-chain hydrocarbon group with a carbon number of 10-40.
4. The conductive resin composition according to claim 1 or 2, wherein the (d 1) acid anhydride-based curing agent, the (d 2) thiol-based curing agent or the (d 3) phenol-based curing agent is in a liquid state at 25 ℃.
5. A conductive film comprising the conductive resin composition according to claim 1 or 2, wherein the volume resistivity is less than 1.0X10 -2. Omega. Cm.
6. A conductive ink comprising the conductive resin composition according to claim 1 or 2.
7. A conductive adhesive comprising the conductive resin composition according to claim 1 or 2.
8. A circuit connecting material comprising the electroconductive resin composition according to claim 1 or 2.
Applications Claiming Priority (10)
Application Number | Priority Date | Filing Date | Title |
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JP2021-175022 | 2021-10-26 | ||
JP2021-175020 | 2021-10-26 | ||
JP2021-175021 | 2021-10-26 | ||
JP2021-175019 | 2021-10-26 | ||
JP2022-169228 | 2022-10-21 | ||
JP2022-169227 | 2022-10-21 | ||
JP2022169230A JP2023064724A (en) | 2021-10-26 | 2022-10-21 | Conductive resin composition |
JP2022-169229 | 2022-10-21 | ||
JP2022-169230 | 2022-10-21 | ||
PCT/JP2022/039718 WO2023074680A1 (en) | 2021-10-26 | 2022-10-25 | Conductive resin composition |
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CN118119662A true CN118119662A (en) | 2024-05-31 |
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CN202280070457.2A Pending CN118119662A (en) | 2021-10-26 | 2022-10-25 | Conductive resin composition |
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