WO2008041426A1 - Polyamideimide resin, adhesive agent, material for flexible substrate, flexible laminate, and flexible print wiring board - Google Patents
Polyamideimide resin, adhesive agent, material for flexible substrate, flexible laminate, and flexible print wiring board Download PDFInfo
- Publication number
- WO2008041426A1 WO2008041426A1 PCT/JP2007/066100 JP2007066100W WO2008041426A1 WO 2008041426 A1 WO2008041426 A1 WO 2008041426A1 JP 2007066100 W JP2007066100 W JP 2007066100W WO 2008041426 A1 WO2008041426 A1 WO 2008041426A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- adhesive
- polyimide film
- group
- resin
- adhesive layer
- Prior art date
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- 229920005989 resin Polymers 0.000 title claims abstract description 114
- 239000011347 resin Substances 0.000 title claims abstract description 114
- 239000004962 Polyamide-imide Substances 0.000 title claims abstract description 80
- 229920002312 polyamide-imide Polymers 0.000 title claims abstract description 80
- 239000000853 adhesive Substances 0.000 title claims description 73
- 239000000463 material Substances 0.000 title claims description 12
- 239000000758 substrate Substances 0.000 title claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910000071 diazene Inorganic materials 0.000 claims abstract description 22
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 12
- 230000001070 adhesive effect Effects 0.000 claims description 72
- 229920001721 polyimide Polymers 0.000 claims description 51
- 229910052751 metal Inorganic materials 0.000 claims description 36
- 239000002184 metal Substances 0.000 claims description 36
- 239000011888 foil Substances 0.000 claims description 35
- 239000012790 adhesive layer Substances 0.000 claims description 33
- 150000001412 amines Chemical class 0.000 claims description 18
- 239000003822 epoxy resin Substances 0.000 claims description 17
- 229920000647 polyepoxide Polymers 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000004642 Polyimide Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 229910000679 solder Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004018 acid anhydride group Chemical group 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- -1 polyoxypropylene Polymers 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 42
- 238000003786 synthesis reaction Methods 0.000 description 42
- 150000004985 diamines Chemical class 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- PJEXUIKBGBSHBS-UHFFFAOYSA-N 1-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCN1CCCC1=O PJEXUIKBGBSHBS-UHFFFAOYSA-N 0.000 description 9
- 239000002966 varnish Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 6
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000011889 copper foil Substances 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- NMWCVZCSJHJYFW-UHFFFAOYSA-M sodium;3,5-dichloro-2-hydroxybenzenesulfonate Chemical compound [Na+].OC1=C(Cl)C=C(Cl)C=C1S([O-])(=O)=O NMWCVZCSJHJYFW-UHFFFAOYSA-M 0.000 description 5
- 229920006259 thermoplastic polyimide Polymers 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 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 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 4
- 238000004544 sputter deposition Methods 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 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 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 238000009823 thermal lamination Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- OCDXZFSOHJRGIL-UHFFFAOYSA-N cyclohexyloxycyclohexane Chemical compound C1CCCCC1OC1CCCCC1 OCDXZFSOHJRGIL-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000007731 hot pressing Methods 0.000 description 2
- 150000003949 imides Chemical group 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 238000011191 terminal modification Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- VITYLMJSEZETGU-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5-decafluoro-n,n'-diphenylpentane-1,5-diamine Chemical compound C=1C=CC=CC=1NC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)NC1=CC=CC=C1 VITYLMJSEZETGU-UHFFFAOYSA-N 0.000 description 1
- JLTHXLWCVUJTFW-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoro-n,n'-diphenylbutane-1,4-diamine Chemical compound C=1C=CC=CC=1NC(F)(F)C(F)(F)C(F)(F)C(F)(F)NC1=CC=CC=C1 JLTHXLWCVUJTFW-UHFFFAOYSA-N 0.000 description 1
- UMMYYBOQOTWQTD-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-n,n'-diphenylpropane-1,3-diamine Chemical compound C=1C=CC=CC=1NC(F)(F)C(F)(F)C(F)(F)NC1=CC=CC=C1 UMMYYBOQOTWQTD-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KFGVDCBVGNMCJC-UHFFFAOYSA-N 2-hydrazinylbenzoic acid Chemical compound NNC1=CC=CC=C1C(O)=O KFGVDCBVGNMCJC-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- BDSPLIQKGRTNCG-UHFFFAOYSA-N 3,4-dimethylcyclohexa-1,5-diene-1,3-diamine Chemical group CC1C=CC(N)=CC1(C)N BDSPLIQKGRTNCG-UHFFFAOYSA-N 0.000 description 1
- PQFRTJPVZSPBFI-UHFFFAOYSA-N 3-(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=CC=CC(C(F)(F)F)=C1N PQFRTJPVZSPBFI-UHFFFAOYSA-N 0.000 description 1
- WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- QNJWXYRVQVNUQC-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(2-phenylphenyl)aniline Chemical group C1(=C(C=CC=C1)C1=C(C=CC(=C1)N)C1=CC=C(N)C=C1)C1=CC=CC=C1 QNJWXYRVQVNUQC-UHFFFAOYSA-N 0.000 description 1
- LOIBXBUXWRVJCF-UHFFFAOYSA-N 4-(4-aminophenyl)-3-phenylaniline Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC=C1 LOIBXBUXWRVJCF-UHFFFAOYSA-N 0.000 description 1
- WYHSHHJLHFEEFE-UHFFFAOYSA-N 4-(4-aminophenyl)-6,6-dimethylcyclohexa-1,3-dien-1-amine Chemical compound C1=C(N)C(C)(C)CC(C=2C=CC(N)=CC=2)=C1 WYHSHHJLHFEEFE-UHFFFAOYSA-N 0.000 description 1
- KHYXYOGWAIYVBD-UHFFFAOYSA-N 4-(4-propylphenoxy)aniline Chemical compound C1=CC(CCC)=CC=C1OC1=CC=C(N)C=C1 KHYXYOGWAIYVBD-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- BDBZTOMUANOKRT-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)propan-2-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCC(N)CC1 BDBZTOMUANOKRT-UHFFFAOYSA-N 0.000 description 1
- VMHKBUVJDUPCDZ-UHFFFAOYSA-N 4-[2-[4-amino-2-(trifluoromethyl)phenoxy]phenoxy]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1OC1=CC=CC=C1OC1=CC=C(N)C=C1C(F)(F)F VMHKBUVJDUPCDZ-UHFFFAOYSA-N 0.000 description 1
- XZJANRQATNWFFF-UHFFFAOYSA-N 4-[3-(4-aminocyclohexyl)oxyphenoxy]cyclohexan-1-amine Chemical compound C1CC(N)CCC1OC1=CC=CC(OC2CCC(N)CC2)=C1 XZJANRQATNWFFF-UHFFFAOYSA-N 0.000 description 1
- AILCNTDXHZLKOA-UHFFFAOYSA-N 4-[4-(4-aminocyclohexyl)oxyphenoxy]cyclohexan-1-amine Chemical compound C1CC(N)CCC1OC(C=C1)=CC=C1OC1CCC(N)CC1 AILCNTDXHZLKOA-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- NGYMJNRSTWQKNP-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminocyclohexyl)oxycyclohexyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]cyclohexyl]oxycyclohexan-1-amine Chemical compound C1CC(N)CCC1OC1CCC(C(C2CCC(CC2)OC2CCC(N)CC2)(C(F)(F)F)C(F)(F)F)CC1 NGYMJNRSTWQKNP-UHFFFAOYSA-N 0.000 description 1
- ARNCIZKBHIFXMN-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenoxy]-1,1,1,3,3,3-hexafluoropropan-2-yl]oxyphenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC(C(F)(F)F)(C(F)(F)F)OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 ARNCIZKBHIFXMN-UHFFFAOYSA-N 0.000 description 1
- UVXHGOCKNVBQIT-UHFFFAOYSA-N 4-[4-[4-(4-aminocyclohexyl)oxycyclohexyl]sulfonylcyclohexyl]oxycyclohexan-1-amine Chemical compound C1CC(N)CCC1OC1CCC(S(=O)(=O)C2CCC(CC2)OC2CCC(N)CC2)CC1 UVXHGOCKNVBQIT-UHFFFAOYSA-N 0.000 description 1
- HYDATEKARGDBKU-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]phenoxy]aniline Chemical group C1=CC(N)=CC=C1OC1=CC=C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HYDATEKARGDBKU-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31515—As intermediate layer
- Y10T428/31522—Next to metal
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31681—Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31721—Of polyimide
Definitions
- Polyamideimide resin adhesive, flexible substrate material, flexible laminate and flexible printed wiring board
- the present invention relates to a polyamideimide resin, an adhesive, a flexible substrate material, a flexible laminate, and a flexible printed wiring board.
- a flexible printed wiring board is a flexible wiring board in which a conductor circuit is formed on the surface of a polymer insulating film, and has recently been widely used as a means for achieving downsizing and high density of electronic devices. .
- the demand for flexible printed wiring boards with double-sided metal foil is growing significantly.
- an aromatic polyimide film is generally used as a polymer insulating film.
- a flexible printed wiring board with double-sided metal foil using this is manufactured by a method in which polyimide films with metal foil with metal foil laminated on one side are bonded together with an adhesive mainly composed of epoxy resin or acrylic resin. It had been. For this reason, the printed wiring board's heat resistance, chemical resistance, flame retardancy, electrical properties, and adhesion properties are dominated by the adhesive used! /, And the excellent properties of polyimide are sufficient! / I could't blur! /
- thermoplastic polyimide film is used as an adhesive, and the polyimide film with metal foil is heat-sealed through the thermoplastic polyimide film (for example, Patent Documents 1 and 2). reference).
- a method of directly forming a metal layer by sputtering on both surfaces of a polyimide film is also known (see, for example, Patent Document 3).
- thermoplastic polyimide As an adhesive, does not always have sufficient heat resistance of thermoplastic polyimide, and thus has insufficient resistance to thermal history.
- manufacturing equipment becomes complicated due to a high molding temperature for heat fusion.
- a special apparatus for performing sputtering is required, and a plating process and a heating and heating process may be required, resulting in a problem that the manufacturing process becomes complicated.
- thermosetting adhesive that is cured by a combination of a heat-resistant resin such as a polyamide-imide resin and a thermosetting resin has been studied (for example, And Patent Documents 4 and 5).
- Patent Document 1 Japanese Patent No. 03-104185
- Patent Document 2 JP 2004 230670 A
- Patent Document 3 Japanese Patent No. 3447070
- Patent Document 4 Japanese Patent Publication No. 11 217503
- Patent Document 5 Japanese Unexamined Patent Application Publication No. 2004-179237
- the conventional polyamideimide resin adhesive has a problem that the adhesive strength with the polyimide is greatly reduced when moisture is absorbed.
- the present invention is intended to suppress the decrease in adhesive strength with polyimide when moisture is absorbed while maintaining excellent heat resistance in an adhesive using a polyamide-imide resin.
- the polyamideimide resin according to the present invention is obtained by a method including a step of reacting diimide dicarboxylic acid and aromatic diisocyanate, and diimide dicarboxylic acid is
- the compound represented by the following general formula (1) contains 40 mol% or more and the compound represented by the following general formula (2) contains 20 mol% or more.
- n 1 represents an integer from !! to 100
- R 1 and R 2 each independently represent a divalent organic group
- R 4 each independently Represents an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 18 carbon atoms, and a plurality of R 3 and R 4 in the same molecule may be the same or different
- n 2 is from! Indicates an integer.
- the adhesive strength with the polyimide is sufficiently reduced when moisture is absorbed while maintaining excellent heat resistance. Can be suppressed.
- the polyamide-imide resin according to the present invention preferably has at least one functional group selected from the group consisting of a carboxyl group, an amino group, an acid anhydride group and a mercapto group at the terminal. Thereby, it becomes possible to further improve the heat resistance of the adhesive.
- a polyamide-imide resin-based adhesive in which a decrease in adhesive strength with polyimide when moisture is absorbed is suppressed while maintaining excellent heat resistance.
- thermoplastic polyimide as an adhesive or the case of forming a metal foil directly on a polyimide film by sputtering, it is possible to perform a process such as adhesion with simple equipment.
- FIG. 1 is a cross-sectional view showing an embodiment of an adhesive sheet.
- FIG. 2 is a cross-sectional view showing an embodiment of a cover lay.
- FIG. 3 is a cross-sectional view showing an embodiment of a flexible laminate.
- FIG. 4 is a cross-sectional view showing an embodiment of a flexible laminate.
- FIG. 5 is a cross-sectional view showing an embodiment of a flexible printed wiring board.
- FIG. 6 is a cross-sectional view showing an embodiment of a flexible printed wiring board.
- FIG. 7 is a cross-sectional view showing one embodiment of a flexible printed wiring board.
- the polyamide-imide resin according to the present embodiment generates a polyamide-imide resin by reacting diimide dicarboxylic acid with an aromatic diisocyanate by reacting diamine with trimellitic anhydride, and reacting diimide dicarboxylic acid with aromatic diisocyanate. Obtained by a method including the steps of: A polymerization reaction between diimide dicarboxylic acid and aromatic diisocyanate produces a polyamideimide resin which is a polymer having an amide group and an imide group in the main chain.
- the polyamideimide resin according to the present embodiment is not limited to the one obtained by the above method unless it deviates from the gist of the present invention.
- the polyamideimide resin according to the present invention may be obtained by an acid chloride method in which trimellitic anhydride is reacted with diamine.
- the diamine used for producing the diimide dicarboxylic acid includes at least a polyoxypropylene diamine represented by the following general formula (10) and a siloxandamamine represented by the following general formula (20).
- diimide dicarboxylic acid represented by the above formula (1) or (2) is produced.
- a diamine mixture containing 5 to 100 mol% of the polyoxyproplendiamine and siloxane diamine is reacted with trimellitic anhydride. More preferably, a diamine mixture containing 40 mol% or more of polyoxypropylenediamine and 20 mol% or more of siloxane diamine is reacted with trimellitic anhydride.
- trimellitic anhydride a diamine mixture containing 40 mol% or more of polyoxypropylenediamine and 20 mol% or more of siloxane diamine is reacted with trimellitic anhydride.
- a mixture of diimide dicarboxylic acids containing 40 mol% or more of the compound represented by the formula (1) and 20 mol% or more of the compound represented by the formula (2) can be obtained.
- an adhesive having a particularly excellent balance of adhesive strength, moisture resistance, and heat resistance can be obtained. If the ratio of polyoxypropylene diamine is less than 40 mol%, the adhesion and moisture resistance tend to be lowered
- diimide dicarboxylic acid instead of using the diamine mixture as described above, polyoxypropylenediamine and siloxane diamine were separately reacted with trimellitic anhydride to produce diimide dicarboxylic acid. Mix each diimide dicarboxylic acid in a certain ratio and react with aromatic diisocyanate.
- polyoxypropylene diamines examples include Jeffamine D-230 (Mitsui Chemicals Fine Co., Ltd., Amine equivalent: 115, trade name), Jeffamine D-400 (Mitsui Chemical Fine Co., Ltd.) Product name, Amine equivalent: 200), Dipharmin D-2000 (Mitsui Chemical Fine Co., Ltd., product name, Amine equivalent: 1000) and Jeffamine D-4000 (Mitsui Chemical Fine Co., Ltd., trade name) , Amine equivalent: 2000) is commercially available. Of these, it is preferable to use Jeffamine D2000 with a large amine equivalent! /.
- the amine equivalent of polyoxyproplendiamine is preferably 500-1500 g / eq. These are used alone or in combination of two or more.
- R 1 and R 2 are each independently a divalent organic group.
- R 3 and R 4 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 18 carbon atoms.
- R 1 and R 2 are an alkylene group having 1 to 6 carbon atoms, a phenyl group which may have a substituent (preferably an alkyl group having 1 to 3 carbon atoms or a halogen atom), or a substituent (preferably Is preferably a naphthalene group which may have an alkyl group having 1 to 3 carbon atoms or a halogen atom.
- R 3 and R 4 are preferably a phenyl group which may have a substituent (preferably an alkyl group having 3 to 3 carbon atoms or a halogen atom), or an alkyl group having 1 to 3 carbon atoms.
- Siloxane diamine is, for example, an amino-modified silicone oil X-22-161AS.
- an alicyclic diamine and / or an aromatic diamine can be used in combination with the above diamine.
- alicyclic diamines include 2, 2 bis [4- (4 aminocyclohexyl cyclohexyl) cyclohexyl] propane, bis [4 (3-aminocyclohexyl) cyclohexyl] sulfone, bis [ 4 4 Aminocyclohexyl) cyclohexene] sulfone, 2, 2 bis [4 4 Aminocyclohexyloxy) cyclohexyl] xafluoropropane, bis [4 mono (4 aminocyclohexyloxy) cycloto Xyl] methane, 4, 4 'bis (4 aminocyclohexyloxy) dicyclohexyl, bis [4 4 aminocyclohexyloxy) cyclohexyl] ether, bis [4 mono (4 monoaminocyclohexyl
- aromatic diamines include p-, m- or o phenylenediamine, 2,4-diaminotonolene, 2,5 diaminotonolene, 2,4 diaminoxylene, diaminodiurene, 1 , 5 Diaminonaphthalene, 2,6 Diaminonaphthalene, Benzidine, 4,4'-Diaminoterphenyl, 4,4'-Diaminoquaterphenyl, 4,4'-Diaminodiphenylmethane, 1, 2 Bis (anilino) ethane, 4,4′-diaminodiphenyl ether, diaminodiphenyl sulfone, 2,2-bis (paminophenol) propane, 2,2-bis (paminophenylene) hexafluoropropane, 2,6 diaminonaphthalene, 3,3 dimethylbenzidine, 3,3 'dimethyl-4,4'-diaminodiphenyl ether,
- the diimide dicarboxylic acid mixture to be reacted with the aromatic diisocyanate contains 40 to 80 mol% of the diimide dicarboxylic acid of the formula (1) and 20 to 60 mol% of the diimide dicarboxylic acid of the formula (2).
- a polyamidoimide resin containing polyoxypropylene chains and polysiloxane chains is produced.
- the aromatic diisocyanate to be reacted with diimide dicarboxylic acid is a diisocyanate having an isocyanate group bonded to an aromatic ring, and is obtained, for example, by reaction of an aromatic diamine with phosgene.
- Specific examples of the aromatic diisocyanate include tolylene diisocyanate ether diisocyanate and phenylene 1,3-diisocyanate. These may be used alone or in combination of two or more.
- the polymerization reaction between diimide dicarboxylic acid and aromatic diisocyanate is usually performed by N-methylol-2-pyrrolidone (NMP), N, N dimethylformamide (DMF), N, N dimethylacetamide (DMAC), dimethyl sulfoxide. It is carried out in a solvent selected from (DMSO), dimethyl sulfate, sulfolane, ⁇ -butyrolatatone, cresonole, phenol, halogenated phenol, cyclohexane and dioxane.
- the reaction temperature is preferably 0 to 200 ° C.
- the polyamideimide resin is formed in a solution state. Use the solution without isolating the polyamideimide resin from the solution to prepare the adhesive varnish as it is. Can do.
- the polyimide resin produced by the polymerization reaction of diimide dicarboxylic acid and aromatic diisocyanate preferably introduces a reactive functional group that reacts with the epoxy resin at the terminal.
- the reactive functional group is preferably selected from the group consisting of a carboxyl group, an amino group, an acid anhydride group and a mercapto group.
- the amino group may be introduced as imidazole. Among these, a carboxyl group and an amino group are preferable, and a carboxyl group is most preferable! /.
- the reactive functional group is introduced, for example, by a method in which a compound having one or more reactive functional groups is reacted with a terminal functional group (typically an isocyanate group) of a polyamideimide resin.
- a terminal functional group typically an isocyanate group
- the polyamideimide resin comprises phthalic acid, trimellitic acid, maleic acid, biphthalic acid, naphthalenedicarboxylic acid, amaminonaphthalene acid, aminoaminobenzoic acid, diaminonaphthalene, diaminobenzoic acid, phenyldiamin and derivatives thereof.
- a reactive functional group is introduced into the terminal by reaction with a compound selected from the group.
- the carboxylic acid equivalent of the polyamideimide resin is preferably ⁇ 3,000 to 15000 g / eq., More preferably ⁇ 5,000 to 1000 Og / eq. .
- the carboxylic acid equivalent exceeds 15000 g / eq., The effect of improving the heat resistance by terminal modification tends to be small, and when it is less than 53000 g / eq., Unreacted residues tend to be generated in the system.
- the amine equivalent of the polyamideimide resin is preferably ⁇ 3,000 to 15000 g / eq., More preferably ⁇ 5000 to 10000 g / eq.
- the adhesive according to the present embodiment contains the polyamideimide resin as described above and an epoxy resin.
- the adhesive according to the present embodiment is particularly suitably used as an adhesive for polyimide for bonding an adherend such as a polyimide film made of polyimide to other members.
- the epoxy resin a polyfunctional epoxy compound having two or more epoxy groups is preferable.
- a polyhydric phenol such as bisphenol A, a nopolac-type phenol resin, an ortho-cresol nopolac-type phenol resin or a polyhydric alcohol such as 1,4 butanediol is reacted with epichlorohydrin.
- N-glycidyl derivative of a compound having polyglycidyl ester, amine, amide or heterocyclic nitrogen base obtained by reacting polyglycidyl ether, polyphthalic acid such as phthalic acid and hexahydrophthalic acid with epichlorohydrin
- alicyclic epoxy resins such as dicyclopentagen type epoxy resins are particularly preferable.
- Epoxy resin can be used alone or in combination.
- the content of the epoxy resin is usually in the range of 10 to 50 parts by mass with respect to 100 parts by mass of the polyamideimide resin.
- the adhesive according to the present embodiment may further contain an epoxy resin curing agent and / or a curing accelerator.
- the curing agent and curing accelerator are not particularly limited as long as they react with the epoxy resin and / or accelerate the curing.
- amines, imidazoles, polyfunctional phenols and acid anhydrides can be used.
- Examples of amines that can be used include dicyandiamide, diaminodiphenylmethane, and guanylurea.
- polyfunctional phenols for example, hydroquinone, resorcinol, bisphenol A and their halogen compounds, as well as nopolac-type phenol resins and resole-type phenol resins which are condensates with formaldehyde can be used.
- acid anhydrides for example, phthalic anhydride, benzophenone tetracarboxylic dianhydride, and methyl hymic acid can be used.
- imidazoles such as alkyl group-substituted imidazole and benzimidazole can be used.
- An adhesive containing a polyamide-imide resin, an epoxy resin, and any other component is an adhesive dissolved or dispersed in a solvent when applied to an adherend such as a polyimide film or other support. It is preferably used in a varnish state. Solvents used in the varnish include, for example, N-methyl 2-pyrrolidone (NMP), N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAC), dimethyl sulfoxide (DMSO), dimethyl sulfate, sulfolane , ⁇ -butyral rataton, cresol, phenol, halogenated phenol, hexane and dioxane. Preferably used for the synthesis of polyamide-imide resin The added solvent is used as a solvent for the adhesive varnish.
- NMP N-methyl 2-pyrrolidone
- DMF N, N-dimethylformamide
- DMAC N-dimethylacetamide
- DMSO dimethyl s
- the normal adhesive force at the interface between the polyimide film and the adhesive layer is 1. OkN / m or more.
- the adhesive strength is maintained at a value of 90% or more before the test, and the solder heat resistance measured by the float method in a solder bath at 288 ° C. is 30 seconds or more.
- the above adhesive strength and solder heat resistance are obtained by applying an adhesive or adhesive varnish with a thickness of 10 m on a polyimide film, bonding another polyimide film with an adhesive in between, and heating in that state. It is measured using a test piece obtained by curing.
- the above adhesive force is an average load when the polyimide film adhesive layer interface is peeled off under the conditions of a peeling angle of 90 degrees and a peeling speed of 50 mm / min.
- Adhesive strength after the PCT test is measured using a test piece that is allowed to stand for 3 hours in an atmosphere of 121 ° C, 2 atm and RH100%. According to the adhesive according to the present embodiment, the adhesive strength after the PCT test measured under these conditions does not decrease more than 10% from the adhesive strength before the PCT test, that is, in a normal state.
- a flexible substrate material, a flexible laminate, or a flexible printed wiring board including an adhesive layer made of the adhesive is configured.
- Examples of the flexible substrate material include an adhesive sheet shown in FIG. 1 and a coverlay shown in FIG.
- the adhesive sheet la in FIG. 1 includes an adhesive layer 10 formed from the adhesive according to the present embodiment.
- the coverlay lb in FIG. 2 includes a polyimide film 21 and an adhesive layer 10 provided on the polyimide film 21 and formed from the adhesive according to the present embodiment.
- the adhesive forming the adhesive layer 10 is usually formed into a film by substantially removing the solvent.
- the thickness of the polyimide film 21 is about! ⁇ 100 m.
- the thickness of the adhesive layer 10 is usually about 0.5 to 50 111.
- a commercially available polyimide film 21 can be used.
- Examples of commercially available polyimide films include Upilex (trade name, manufactured by Ube Industries, Ltd.), Kapton (trade name, manufactured by Toray 'Dupont Co., Ltd.), and Abical (trade name, Kaneiki Co., Ltd.). Is mentioned.
- the flexible laminate 2a shown in FIG. 3 is densely packed on the resin film 20 and one surface of the resin film 20. Interposed between the two resin films 5 with metal foil and the two resin films 5 with metal foil disposed opposite to each other with the resin film 20 facing inward. And an adhesive layer 10 for bonding them together.
- the flexible laminate 2b shown in FIG. 4 includes a resin film 20 and a resin film 5 with a metal foil having a metal foil 30 provided in close contact with one surface of the resin film 20, and the resin film 5 with the metal foil. And a resin film 22 disposed opposite to each other on the resin film 20 side, and an adhesive layer 10 interposed between the resin film 5 with metal foil and the resin film 22 to bond them together.
- the metal foil 30 a foil of copper, aluminum, iron, gold, silver, nickel, palladium, chromium, molybdenum, or an alloy thereof is preferably used. Among these, copper foil is preferable.
- the surface of the metal foil 30 is mechanically or chemically treated by chemical roughening, corona discharge, sanding, plating, aluminum alcoholate, aluminum chelate, silane coupling agent, etc. Being! /, Even! /
- the flexible laminate is obtained, for example, by a method in which a resin film with a metal foil is bonded to another resin film with a metal foil or a resin film via an adhesive layer.
- the bonding method include hot pressing and thermal lamination. In any case, it is essential to heat in the range of 80 to 300 ° C, preferably 120 ° C to 200 ° C. If it is less than 80 ° C, it is difficult to bond with sufficient adhesive strength, and if it exceeds 300 ° C, it may be accompanied by thermal decomposition of the polyamideimide resin in the adhesive layer.
- the part to be shelled is preheated to 80 ° C to 300 ° C, and the part to be heated and bonded and the part to be bonded are 80 ° C to By keeping the temperature at 300 ° C, it is possible to perform the bonding effectively. Moreover, it is preferable to pressurize with heating. In the case of hot pressing, it is desirable to pressurize at IMPa or more, preferably 2 MPa or more and 5 MPa or less, and in the case of thermal lamination, 10 kN / m or more, preferably 50 kN / m or more and 200 kN / m or less.
- FIG. 5 is cross-sectional views showing one embodiment of a flexible printed wiring board.
- the flexible printed wiring board 3a shown in FIG. 5 is formed on both surfaces of an insulating layer composed of two resin films 20 arranged opposite to each other and an adhesive layer 10 interposed therebetween.
- a metal foil 31 forming a wiring pattern (conductive pattern).
- the metal foil 31 is formed, for example, by removing a part of the metal foil 30 included in the flexible laminate 2a and patterning it.
- the metal foil 30 is patterned by a method such as photolithography.
- the flexible printed wiring board can be obtained by removing the metal foil 30 from the flexible laminated board 2a and directly drawing a conductive material on the exposed resin film 20 to form a conductive pattern.
- the flexible printed wiring board 3b shown in FIG. 6 has two resin films arranged to face each other.
- the flexible printed wiring board 3b is obtained by, for example, a method of forming a wiring pattern of the flexible printed wiring board 3a and bonding the resin film 22 on each metal foil 31.
- the flexible printed wiring board 3c shown in FIG. 7 is composed of two resin films arranged to face each other.
- the adhesive layer 10 in the insulating layer bonds the two resin films 20 together.
- the adhesive layer 10 in the cover lay lb bonds the polyimide film 21 and the resin film 20 or the metal foil 31 forming the wiring pattern.
- the flexible printed wiring board 3c is obtained, for example, by using the cover lay lb of FIG. 2 instead of the resin film 20 in the production of the flexible printed wiring board.
- the adhesive layer 10 constituting the flexible laminate and the flexible printed wiring board are both formed from the adhesive according to the above-described embodiment, and the polyamide-imide resin contained in the adhesive layer 10 is used. At least a part of the resin is crosslinked by reaction with an epoxy resin. As the resin films 20 and 22, a polyimide film is usually used.
- Example 1
- Polyamideimide resin was synthesized using the following diamine.
- Wandamine HM (trade name, manufactured by Shin Nippon Rika Co., Ltd.): (4,4'-diamino) dicyclohexylmethane
- TMA trimellitic anhydride
- NMP N-methyl-2-pyrrolidone
- Phenylylenediamine was added in an amount of 0.1 lg (0.9 mmol) to an unmodified polyamideimide resin solution obtained in the same manner as in Synthesis Example 8 and reacted under the same conditions as in Synthesis Example 13 to have an amino group at the terminal.
- a solution of polyamideimide resin 15 was obtained.
- the amine equivalent of the polyamideimide resin 15 was measured in the same manner as in Synthesis Example 13.
- Polyamideimide resin having a phenolic hydroxyl group at the terminal by adding 0.8 g of p-aminophenol to a solution of unmodified polyamideimide resin obtained in the same manner as in Synthesis Example 8 and reacting under the same conditions as in Synthesis Example 13. 16 Solution was obtained.
- the hydroxyl group equivalent (g / eq.) Of polyamideimide resin 16 was measured by the acetyl chloride-potassium hydroxide method.
- Polyimide film (Kapton (tradename), a thickness of 2 5 m, Toray. Dupont Ltd.), was coated with an adhesive varnish in a thickness of 10 m using Abu Riketa.
- An adhesive layer was formed by drying at 150 ° C. using an oven to obtain a polyimide film with an adhesive.
- Adhere another Kapton similar to the above on the adhesive layer side, and heat-press with a hot press under conditions of 200 ° C, 4 MPa, 1 hour, and two polyimide films (kapton) through the adhesive layer To obtain a flexible substrate material bonded.
- a resin film with copper foil in which a copper foil is provided on one side of a polyimide film (MCF-50001 (trade name), polyimide film thickness 25 m, copper foil thickness 18 mm, Hitachi Kasei Kogyo Co., Ltd.) was used, and an adhesive varnish was applied to the polyimide film side to a thickness of 10 ⁇ .
- MCF-50001 trade name
- polyimide film thickness 25 m copper foil thickness 18 mm
- Hitachi Kasei Kogyo Co., Ltd. Hitachi Kasei Kogyo Co., Ltd.
- a 1 cm wide test piece was cut out from the flexible substrate material. One surface of this test piece was fixed, and the polyimide film-adhesive layer interface was peeled off at a peel angle of 90 degrees and a peel speed of 50 mm / min, and the average load at that time was determined as the adhesive force.
- the adhesive strength of the flexible substrate material after the normal state and the accelerated moisture absorption test (PCT test) was evaluated. The PCT test was performed by leaving the test piece for 3 hours in an atmosphere of 121 ° C, 2 atm and RH 100%.
- a 4 cm square test piece was cut out from the flexible substrate material produced using MCF-5001. After drying this at 130 ° C for 1 hour, the solder heat resistance was measured by a one-piece method using a 288 ° C soldering iron.
- polyamidoimide resin 14 having a polyoxypropylene diamine ratio of 40 mol% or more and a siloxane diamine ratio of 20 mol% or more was used.
- the normal adhesive strength was clearly improved as compared with the case of polyamideimide resin 57, and no decrease in the adhesive strength was observed even after moisture absorption by the PCT test.
- polyamideimide resin 7 having a siloxane diamine ratio of less than 20 mol% the adhesive strength after moisture absorption was maintained at a good level! /, But the solder heat resistance was inferior! /.
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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KR1020097006792A KR101441990B1 (ko) | 2006-10-04 | 2007-08-20 | 폴리아미드이미드 수지, 접착제, 플렉시블 기판 재료, 플렉시블 적층판 및 플렉시블 인쇄배선판 |
CN2007800372002A CN101522744B (zh) | 2006-10-04 | 2007-08-20 | 聚酰胺酰亚胺树脂、粘接剂、挠性基板材料、挠性层叠板及挠性印刷电路板 |
EP20070792714 EP2070961A4 (en) | 2006-10-04 | 2007-08-20 | POLYAMIDEIMIDE RESIN, ADHESIVE AGENT, FLEXIBLE SUBSTRATE MATERIAL, FLEXIBLE LAMINATE, AND FLEXIBLE CONNECTION TABLE FOR PRINTER |
JP2008537432A JP5287247B2 (ja) | 2006-10-04 | 2007-08-20 | ポリアミドイミド樹脂、接着剤、フレキシブル基板材料、フレキシブル積層板及びフレキシブル印刷配線板 |
US12/444,234 US8956732B2 (en) | 2006-10-04 | 2007-08-20 | Polyamideimide resin, adhesive agent, material for flexible substrate, flexible laminate, and flexible print wiring board |
Applications Claiming Priority (4)
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JP2006-273005 | 2006-10-04 | ||
JP2006273005 | 2006-10-04 | ||
JP2007-059093 | 2007-03-08 | ||
JP2007059093 | 2007-03-08 |
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PCT/JP2007/066100 WO2008041426A1 (en) | 2006-10-04 | 2007-08-20 | Polyamideimide resin, adhesive agent, material for flexible substrate, flexible laminate, and flexible print wiring board |
Country Status (7)
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US (1) | US8956732B2 (ja) |
EP (1) | EP2070961A4 (ja) |
JP (1) | JP5287247B2 (ja) |
KR (1) | KR101441990B1 (ja) |
CN (1) | CN101522744B (ja) |
TW (1) | TWI433863B (ja) |
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2008143253A1 (ja) * | 2007-05-21 | 2008-11-27 | Hitachi Chemical Company, Ltd. | 接着剤組成物及びこれを用いた接着フィルム |
JP2010083958A (ja) * | 2008-09-30 | 2010-04-15 | Hitachi Chem Co Ltd | 多層フレキシブル基板用接着剤及びこれを用いた多層フレキシブル基板材料、積層板並びに印刷配線板 |
WO2010106359A2 (en) | 2009-03-16 | 2010-09-23 | Sun Chemical B.V. | Liquid coverlays for flexible printed circuit boards |
WO2011040399A1 (ja) * | 2009-09-30 | 2011-04-07 | 日立化成工業株式会社 | 樹脂組成物並びにこれを用いたプリプレグ、樹脂付き金属箔、接着フィルム及び金属箔張り積層板 |
WO2011051412A1 (en) | 2009-10-29 | 2011-05-05 | Sun Chemical B.V. | Polyamideimide adhesives for printed circuit boards |
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WO2008143253A1 (ja) * | 2007-05-21 | 2008-11-27 | Hitachi Chemical Company, Ltd. | 接着剤組成物及びこれを用いた接着フィルム |
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WO2016121392A1 (ja) * | 2015-01-30 | 2016-08-04 | パナソニックIpマネジメント株式会社 | 両面金属張積層板及びその製造方法 |
Also Published As
Publication number | Publication date |
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US8956732B2 (en) | 2015-02-17 |
EP2070961A4 (en) | 2012-08-29 |
JP5287247B2 (ja) | 2013-09-11 |
TW200831551A (en) | 2008-08-01 |
CN101522744B (zh) | 2012-02-22 |
KR20090057414A (ko) | 2009-06-05 |
TWI433863B (zh) | 2014-04-11 |
KR101441990B1 (ko) | 2014-09-18 |
US20100170701A1 (en) | 2010-07-08 |
CN101522744A (zh) | 2009-09-02 |
EP2070961A1 (en) | 2009-06-17 |
JPWO2008041426A1 (ja) | 2010-02-04 |
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