JP2022019755A - 異方性導電フィルム - Google Patents
異方性導電フィルム Download PDFInfo
- Publication number
- JP2022019755A JP2022019755A JP2021180149A JP2021180149A JP2022019755A JP 2022019755 A JP2022019755 A JP 2022019755A JP 2021180149 A JP2021180149 A JP 2021180149A JP 2021180149 A JP2021180149 A JP 2021180149A JP 2022019755 A JP2022019755 A JP 2022019755A
- Authority
- JP
- Japan
- Prior art keywords
- conductive film
- anisotropic conductive
- alicyclic epoxy
- epoxy compound
- acid anion
- 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.)
- Granted
Links
- 239000002245 particle Substances 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- -1 oxetane compound Chemical class 0.000 claims abstract description 35
- 239000004593 Epoxy Substances 0.000 claims abstract description 31
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 30
- 238000010538 cationic polymerization reaction Methods 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 17
- 239000011230 binding agent Substances 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 10
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 9
- 150000001768 cations Chemical class 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000013329 compounding Methods 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000013034 phenoxy resin Substances 0.000 claims description 4
- 229920006287 phenoxy resin Polymers 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 claims description 3
- WDNQRCVBPNOTNV-UHFFFAOYSA-N dinonylnaphthylsulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1 WDNQRCVBPNOTNV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 19
- 230000008021 deposition Effects 0.000 abstract 1
- 239000010408 film Substances 0.000 description 81
- 239000010410 layer Substances 0.000 description 25
- 238000011156 evaluation Methods 0.000 description 19
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 238000002156 mixing Methods 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 230000007423 decrease Effects 0.000 description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- 238000002788 crimping Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 238000007373 indentation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- DCOXQQBTTNZJBI-UHFFFAOYSA-N 3-ethyl-3-[[4-[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]phenyl]methoxymethyl]oxetane Chemical group C=1C=C(C=2C=CC(COCC3(CC)COC3)=CC=2)C=CC=1COCC1(CC)COC1 DCOXQQBTTNZJBI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005489 elastic deformation Effects 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 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 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002921 oxetanes Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- AQTIRDJOWSATJB-UHFFFAOYSA-K antimonic acid Chemical compound O[Sb](O)(O)=O AQTIRDJOWSATJB-UHFFFAOYSA-K 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000007771 core particle Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
- H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4064—Curing agents not provided for by the groups C08G59/42 - C08G59/66 sulfur containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Abstract
Description
カチオン重合開始剤が、第4級アンモニウム塩系熱酸発生剤であり、カチオン重合性成分が、脂環式エポキシ化合物と低極性オキセタン化合物とを含有している異方性導電フィルムを提供する。
本発明の異方性導電フィルムは、成膜用成分とカチオン重合性成分とを含有するバインダ組成物と、カチオン重合開始剤と、導電粒子とを含有している。
本発明において、導電粒子を含有保持するバインダ組成物は、成膜用成分とカチオン重合性成分とを含有している。
成膜用成分は、異方性導電フィルムをフィルム化するために使用される成分であり、膜形成能を有する成分である。このような成膜用成分としては、フェノキシ樹脂、エポキシ樹脂、不飽和ポリエステル樹脂、飽和ポリエステル樹脂、ウレタン樹脂、ブタジエン樹脂、ポリイミド樹脂、ポリアミド樹脂、ポリオレフィン樹脂等を挙げることができ、これらの2種以上を併用することができる。これらの中でも、製膜性、加工性、接続信頼性の観点から、フェノキシ樹脂を好ましく使用することができる。
カチオン重合性成分は、異方性導電フィルムを硬化させる成分であり、脂環式エポキシ化合物と低極性オキセタン化合物とを含有している。バインダ組成物中におけるカチオン重合性成分の配合量は、好ましくは10~80質量%、より好ましくは20~60質量%である。この範囲であれば、より高い硬化速度を有するバインダ組成物を与えることができる。
脂環式エポキシ化合物を使用する理由は、汎用のグリシジルエーテル型エポキシ化合物よりも高いその反応性を利用して、異方性導電フィルムに良好な低温速硬化性を付与するためである。このような脂環式エポキシ化合物としては、分子内に2つ以上のエポキシ基を有するものが好ましく挙げられる。これらは液状であっても、固体状であってもよい。具体的には、ジグリシジルヘキサヒドロビスフェノールA、3,4-エポキシシクロヘキセニルメチル-3′,4′-エポキシシクロヘキセンカルボキシレート、ジエポキシビシクロヘキシル等を挙げることができる。中でも、硬化物の光透過性を確保でき、速硬化性にも優れている点から、ジグリシジルヘキサヒドロビスフェノールA、中でもジエポキシビシクロヘキシルを好ましく使用することができる。
本発明においては、脂環式エポキシ化合物に低極性オキセタン化合物を併用する。低極性オキセタン化合物は、双極子モーメントが3.0d以下のオキセタン化合物であり、表面張力が比較的低く、異方性導電フィルムの膜に良好なレベリング性を付与することができ、結果的に異方性導電フィルムの保管ライフ性を向上させることが可能となる。他方、低極性オキセタン化合物は、脂環式エポキシ化合物に由来する異方性導電フィルムの示差走査熱量計(DSC)で測定される反応開始温度と反応終了温度とを上昇させる作用を有する。このような低極性オキセタン化合物としては、3-エチル-3-(2-エチルヘキシロキシメチル)オキセタン、3-エチル-3-ヒドロキシメチルオキセタン、ジ[1-エチル(3-オキセタニル)]メチルエーテル、4,4′-ビス[(3-エチル-3-オキセタニル)メトキシメチル]ビフェニル等が挙げられる。なかでも、表面張力が低く、濡れ性に優れることから、3-エチル-3-(2-エチルヘキシロキシメチル)オキセタン、特に4,4′-ビス[(3-エチル-3-オキセタニル)メトキシメチル]ビフェニルが好ましい。
本発明の異方性導電フィルムは、異方性導電接続を可能とするために、バインダ組成物中に導電粒子を含有する。導電粒子としては、従来公知の異方性導電フィルムに用いられているものの中から適宜選択して使用することができる。例えばニッケル、コバルト、銀、銅、金、パラジウムなどの金属粒子、ハンダなどの合金粒子、金属被覆樹脂粒子などが挙げられる。2種以上を併用することもできる。
本発明の異方性導電フィルムは、カチオン重合開始剤として、スルホニウム塩系熱酸発生剤ではなく第4級アンモニウム塩系熱酸発生剤を含有する。保管ライフ性を向上させるためである。このような第4級アンモニウム塩系熱酸発生剤としては、第4級アンモニウムカチオンと、6フッ化アンチモン酸アニオン、6フッ化リン酸アニオン、トリフルオロメタンスルホン酸アニオン、パーフルオロブタンスルホン酸アニオン、ジノニルナフタレンスルホン酸アニオン、ジノニルナフタレンスルホン酸アニオン、p-トルエンスルホン酸アニオン、ドデシルベンゼンスルホン酸アニオン、またはテトラキス(ペンタフルオロフェニル)ボレートアニオンとの塩等を挙げることができる。また、第4級アンモニウムカチオンとしては、NR1R2R3R4+で表されるカチオンを挙げることができる。ここで、R1、R2、R3及びR4は、直鎖、分岐鎖または環状の炭素数1~12のアルキル基またはアリール基であり、それぞれ水酸基、ハロゲン、アルコキシル基、アミノ基、エステル基等を有していてもよい。
本発明の異方性導電フィルムは、上述したバインダ組成物に導電粒子とカチオン重合開始剤とを、トルエン等の有機溶媒に溶解して塗料とし、その塗料を公知のフィルム化手法を利用してフィルム化することにより製造することができる。
本発明の異方性導電フィルムは、ICチップ、ICモジュール、FPCなどの第1電子部品と、プラスチック基板、ガラス基板、リジッド基板、セラミック基板、FPCなどの第2電子部品とを異方性導電接続する際に好ましく適用することができる。このような本発明の異方性導電フィルムで、第1電子部品と第2電子部品とが異方性導電接続されている接続構造体も本発明の一部である。なお、異方性導電フィルムを用いた電子部品の接続方法としては、公知の手法を利用することができる。
(導電粒子含有層の形成)
フェノキシ樹脂(YP-50、新日鉄住金化学(株))60質量部、脂環式エポキシ化合物としてジエポキシビシクロヘキシル(セロキサイド8000、(株)ダイセル)10質量部、低極性オキセタン化合物(OXBP、宇部興産(株))20質量部、熱カチオン重合開始剤(第4級アンモニウム塩系熱酸発生剤、商品名CXC-1612、楠本化成(株))2質量部、および平均粒径3μmの導電性粒子(Ni/Auメッキ樹脂粒子、AUL704、積水化学工業(株))50質量部を、トルエンに添加し、固形分が50質量%となるよう混合液を調製した。
導電粒子を用いない以外は、導電粒子含有層の形成の際に使用した原材料と同じ原材料をトルエンに添加し、固形分が50質量%となるよう混合液を調製した。
導電粒子含有層に絶縁性樹脂層を、60℃、5MPaでラミネー卜することにより、厚さ50μmの一対のPET剥離フィルムで挟持された異方性導電フィルムを得た。
導電粒子含有層および絶縁性樹脂層における脂環式エポキシ化合物(セロキサイド8000、(株)ダイセル)と低極性オキセタン化合物として4,4′-ビス[(3-エチル-3-オキセタニル)メトキシメチル]ビフェニル(0XBP、宇部興産(株))との配合量(比率)を、表1に示すように変更した以外は、実施例1と同様に異方性導電フィルムを得た。
導電粒子含有層および絶縁性樹脂層における熱カチオン重合開始剤を、表1に示すようにスルホニウム塩系熱酸発生剤(SI-60L、三新化学工業(株))に代えた以外は、実施例1~4と同様に異方性導電フィルムを作成した。
導電粒子含有層及び絶縁性樹脂層における脂環式エポキシ化合物(セロキサイド8000、(株)ダイセル)と低極性オキセタン化合物(0XBP、宇部興産(株))との配合量(比率)を、表1に示すよう変更した以外は、実施例1と同様に異方性導電フィルムを作成した。
各実施例及び比較例で得られた異方性導電フィルムについて、以下に説明するように「保管ライフ特性」、「硬化温度」、「密着特性」及び「反応時間」を試験もしくは測定し、評価した。
一対のPET剥離フィルムに挟持されている異方性導電フィルムを、湿度40%、温度25℃又は30℃に設定されている恒温恒湿室に投入し、投入後24時間毎にサンプリングを行い、以下の仮張り評価および圧着評価を実施し、それらの評価結果から総合的に保管ライフ特性を評価した。得られた結果を表1に示す。
異方性導電フィルムの導電粒子含有層側のPET剥離フィルムを剥離し、導電粒子含有層側から異方性導電フィルムを素ガラスに貼り付け、素ガラスと異方性導電フィルムとの積層体を作製した。この積層体をその素ガラス側が45℃に設定したホットプレートに接触するように載置し、異方性導電フィルム側から手で圧力をかけ、その後、室温にまで冷却した。冷却後、積層体から絶縁性樹脂層側のPET剥離フィルムを剥がし、素ガラスから異方性導電フィルムが剥がれることなく、PET剥離フィルムだけが剥がれるか否かを確認した。
テスト用ICチップとテスト用基板との間に、ICチップ側に絶縁性樹脂層が配置されるよう異方性導電フィルムを挟み、加熱加圧(120℃、60MPa、5秒)し、評価用接続物を作成した。作成した接続物の圧痕状態を確認し、圧痕が薄くならず、消失せずに残存するかを確認した。
仮張り評価において、素ガラスから異方性導電フィルムが剥がれた時点を保管ライフとした。また、仮張り評価において、素ガラスから異方性導電フィルムが剥がれなかった場合でも、圧着評価において、圧痕が薄くなった(消失した)時点を保管ライフとした。
テスト用ICチップとテスト用基板との間に、ICチップ側に絶縁性樹脂層が配置されるよう異方性導電フィルムを挟み、加熱加圧(80℃、90℃、100℃、110℃、又は120℃、60MPa、5秒)し、評価用接続物を得た。この接続物における異方性導電フィルムの反応率を以下に説明するように測定し、その測定結果から硬化温度を決定した。得られた結果を表1に示す。
評価用接続物のICチップを手で摘まんで剥がし、硬化した異方性導電フィルムを露出させ、異方性導電フィルムをサンプリングした。得られたサンプルを、濃度0.1g/mLとなるようアセトニトリルに溶解した。別途、硬化前の異方性導電フィルムを同様の濃度となるようアセトニトリルに溶解し、HPLC-MS(WaterS社製)を用いて、以下の条件にて各モノマーのピーク強度を確認した。硬化後のピーク強度の減少量より各温度での反応率を求め、反応率80%以上となる温度を、硬化温度とした。
流量:0.4mL/min
カラム:10cm、40℃C
注入量:5μL
解析波:210-410nm
テスト用ICチップとテスト用基板との間に、ICチップ側に絶縁性樹脂層が配置されるよう異方性導電フィルムを挟み、加熱加圧(120℃、60MPa、5秒)し、評価用接続物を得た。この接続物に対して、エタック社製、型式EHS-411Mを用いて、プレッシャークッカーテスト(PCT)を実施した。具体的には、得られた評価用接続物を、121℃、2atm、飽和水蒸気雰囲気という条件に設定された恒温恒湿槽に接続物を投入し、24時間毎に以下の密着評価を行った。得られた結果を表1に示す。
PCT試験に投入した接続物の外観確認を行い、異方性導電フィルムとICチップもしく基板との層間で剥離が生じているかを目視観察した。
ランク 基準
〇: IC圧着後、48時間のPCTでも剥離が観察されない場合
△: IC圧着後、24時間のPCTでは剥離が観察されないが、48時間のPCT試験では剥離が観察された場合
×: IC圧着後、PCTを行う前にすでに剥離が観察されていたか、24時間のPCTで剥離が観察された場合
得られた異方性導電フィルムから切り出した約5mgのサンプルを、アルミPAN(TA Instruments Inc.)に格納し、それをDSC測定装置(Q2000,TA Instruments Inc.)にセットし、30℃から250℃まで、10℃/分の昇温速度で示差走査熱量計(DSC)測定を行った。得られたDSCチャートから、発熱ピークが立ち上がった時点の温度を反応開始温度として読み取り、発熱ピークがベースラインに変化した時点の温度を反応終了温度として読み取った。また、反応時間を以下の式に従って算出した。得られた結果を表1に示す。
表1の結果(実施例1と比較例1との対比、実施例2と比較例2との対比、実施例3と比較例3との対比、実施例4と比較例4との対比)から、スルホニウム塩系熱酸発生剤に代えて第4級アンモニウム塩系熱酸発生剤を使用すると、脂環式エポキシ化合物と低極性オキセタン化合物との間の配合比に変動があっても、硬化温度や接続信頼性の評価指標となる密着特性を変化させずに保管ライフを大きく向上させ得ることがわかる。
Claims (9)
- 成膜用成分とカチオン重合性成分とを含有するバインダ組成物と、カチオン重合開始剤と、導電粒子とを含有する異方性導電フィルムであって、
カチオン重合開始剤が、第4級アンモニウム塩系熱酸発生剤であり、カチオン重合性成分が、脂環式エポキシ化合物と低極性オキセタン化合物とを含有している異方性導電フィルム。 - 脂環式エポキシ化合物と低極性オキセタン化合物との配合割合が、質量基準で25:75~60:40である請求項1記載の異方性導電フィルム。
- 脂環式エポキシ化合物と低極性オキセタン化合物との配合割合が、質量基準で45:55~60:40である請求項1記載の異方性導電フィルム。
- 第4級アンモニウム塩系熱酸発生剤が、第4級アンモニウムカチオンと、6フッ化アンチモン酸アニオン、6フッ化リン酸アニオン、トリフルオロメタンスルホン酸アニオン、パーフルオロブタンスルホン酸アニオン、ジノニルナフタレンスルホン酸アニオン、ジノニルナフタレンスルホン酸アニオン、p-トルエンスルホン酸アニオン、ドデシルベンゼンスルホン酸アニオン、またはテトラキス(ペンタフルオロフェニル)ボレートアニオンとの塩である請求項1~3のいずれかに記載の異方性導電フィルム。
- 第4級アンモニウムカチオンが、NR1R2R3R4+で表されるカチオンであり、R1、R2、R3及びR4は、直鎖、分岐鎖または環状の炭素数1~12のアルキル基またはアリール基である請求項4記載の異方性導電フィルム。
- 脂環式エポキシ化合物が、ジグリシジルヘキサヒドロビスフェノールA又はジエポキシビシクロヘキシルであり、低極性オキセタン化合物が、3-エチル-3-(2-エチルヘキシロキシメチル)オキセタン又は4,4′-ビス[(3-エチル-3-オキセタニル)メトキシメチル]ビフェニルである請求項1~5のいずれかに記載の異方性導電フィルム。
- 成膜用成分がフェノキシ樹脂である請求項1~6のいずれかに記載の異方性導電フィルム。
- 示差走査熱量計で測定した反応ピークの反応開始温度が60~80℃であり、反応終了温度が155~185℃である請求項1~7のいずれかに記載の異方性導電フィルム。
- 請求項1~8のいずれかに記載の異方性導電フィルムで、第1電子部品と第2電子部品とが異方性導電接続されている接続構造体。
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JP2003346943A (ja) * | 2002-05-28 | 2003-12-05 | Shin Etsu Polymer Co Ltd | 異方導電接着剤およびヒートシールコネクタ |
JP5268260B2 (ja) * | 2007-01-24 | 2013-08-21 | デクセリアルズ株式会社 | 異方導電性接着剤及び電気装置 |
JP5190665B2 (ja) | 2007-06-15 | 2013-04-24 | デクセリアルズ株式会社 | エポキシ系樹脂組成物 |
JP5172903B2 (ja) | 2010-07-09 | 2013-03-27 | 株式会社エヌ・ティ・ティ・ドコモ | 測位支援装置及び測位支援方法 |
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JP5561199B2 (ja) * | 2011-02-17 | 2014-07-30 | 日立化成株式会社 | 接着剤組成物、回路接続材料、接続体及びその製造方法、並びに半導体装置 |
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JPH09246435A (ja) * | 1996-03-06 | 1997-09-19 | Nippon Perknocks Kk | 半導体の封止方法 |
JP2012062477A (ja) * | 1999-03-26 | 2012-03-29 | Hitachi Chem Co Ltd | 回路用接続部材 |
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