CN107009697A - Copper foil covered stack and printed wiring board - Google Patents
Copper foil covered stack and printed wiring board Download PDFInfo
- Publication number
- CN107009697A CN107009697A CN201710008965.9A CN201710008965A CN107009697A CN 107009697 A CN107009697 A CN 107009697A CN 201710008965 A CN201710008965 A CN 201710008965A CN 107009697 A CN107009697 A CN 107009697A
- Authority
- CN
- China
- Prior art keywords
- copper foil
- foil covered
- oxidant layer
- gluing oxidant
- covered stack
- 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 239000011889 copper foil Substances 0.000 title claims abstract description 70
- -1 aromatic tetracarboxylic acid Chemical class 0.000 claims abstract description 41
- 150000004985 diamines Chemical class 0.000 claims abstract description 29
- 238000004026 adhesive bonding Methods 0.000 claims abstract description 27
- 239000007800 oxidant agent Substances 0.000 claims abstract description 27
- 230000001590 oxidative effect Effects 0.000 claims abstract description 27
- 229920001721 polyimide Polymers 0.000 claims abstract description 20
- 239000000539 dimer Substances 0.000 claims abstract description 17
- 239000004642 Polyimide Substances 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 10
- 150000008064 anhydrides Chemical group 0.000 claims abstract description 10
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 238000004132 cross linking Methods 0.000 claims abstract description 5
- 229920005989 resin Polymers 0.000 claims description 30
- 239000011347 resin Substances 0.000 claims description 30
- 239000003822 epoxy resin Substances 0.000 claims description 26
- 229920000647 polyepoxide Polymers 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 18
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 7
- 239000004643 cyanate ester Substances 0.000 claims description 7
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 abstract description 11
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000011810 insulating material Substances 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 3
- 238000007639 printing Methods 0.000 abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 71
- 239000000203 mixture Substances 0.000 description 60
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 58
- 238000004519 manufacturing process Methods 0.000 description 45
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 33
- 239000010410 layer Substances 0.000 description 30
- 239000002585 base Substances 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 18
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000000853 adhesive Substances 0.000 description 15
- 230000001070 adhesive effect Effects 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 9
- 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 9
- 239000001294 propane Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
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- 239000000126 substance Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 229920005573 silicon-containing polymer Polymers 0.000 description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical compound C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920000106 Liquid crystal polymer Polymers 0.000 description 3
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 3
- IMYZQPCYWPFTAG-UHFFFAOYSA-N Mecamylamine Chemical compound C1CC2C(C)(C)C(NC)(C)C1C2 IMYZQPCYWPFTAG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
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- LERREUOVCXYKGR-UHFFFAOYSA-N (2-phenoxyphenyl)-phenylmethanone Chemical class C=1C=CC=C(OC=2C=CC=CC=2)C=1C(=O)C1=CC=CC=C1 LERREUOVCXYKGR-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
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- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- KCYQMQGPYWZZNJ-BQYQJAHWSA-N hydron;2-[(e)-oct-1-enyl]butanedioate Chemical compound CCCCCC\C=C\C(C(O)=O)CC(O)=O KCYQMQGPYWZZNJ-BQYQJAHWSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 208000001543 infantile parkinsonism-dystonia Diseases 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical class NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- YSZUKWLZJXGOTF-UHFFFAOYSA-N propane Chemical class CCC.CCC YSZUKWLZJXGOTF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 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
- 239000000758 substrate Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920006259 thermoplastic polyimide Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical class C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/02—Physical, chemical or physicochemical properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
- B32B2307/206—Insulating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/50—Properties of the layers or laminate having particular mechanical properties
- B32B2307/538—Roughness
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2311/00—Metals, their alloys or their compounds
- B32B2311/24—Aluminium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
Abstract
The present invention relates to copper foil covered stack and printed wiring board.The present invention provides metal adhesivity, heat resistance, the low-k of insulating materials, the metal-clad stack of low dielectric loss angle tangent characteristic good and the novel printing wiring plate being characterized is lost with low transmission using the metal-clad stack.A kind of copper foil covered stack, it is the copper foil covered stack for possessing the copper foil (3) being layered in via gluing oxidant layer (2) at least unilateral face of dielectric film (1), characterized in that, the thermal coefficient of expansion of dielectric film (1) is 4~30ppm/ DEG C；Gluing oxidant layer (2) contains anhydride group end polyimides (A) and crosslinking component (B), and anhydride group end polyimides (A) is the reaction product of aromatic tetracarboxylic acid's acid anhydride and the diamine monomer comprising dimer type diamine；10 mean roughness (Rz) in the face contacted with gluing oxidant layer (2) of copper foil (3) are 0.1~1.5 μm.
Description
Technical field
The present invention relates to copper foil covered stack and printed wiring board.
Background technology
Flexible printing wiring board (FPWB：Flexible Printed Wiring Board) and printed circuit board (PCB) (PCB：
Printed Circuit Board) and their multiwiring board has been used in mobile communication equipments such as mobile phone, smart mobile phones
Or be widely used in the product such as network associated electronic device, the mainframe computer such as its base station apparatus, server/router.
In recent years, for these products, high frequency telecommunications is used to transmit/handle Large Copacity information at high speed
Number, but high-frequency signal is very easy to decay, therefore, is also required that for multiwiring board and tries to suppress transmission loss as far as possible.
There is conductor losses and dielectric substance loss in transmission loss.When the frequency of electric signal is more than GHz, conductor losses is because of kelvin effect
Surface state dependent on the copper foil used in circuit.On the other hand, Jie of the dielectric substance loss to the insulating materials of near circuitry
Electrical characteristics, particularly dielectric loss angle tangent influence are very big.
As the means for suppressing the transmission loss in multiwiring board, for example, it is contemplated that will be excellent using low dielectric property
Polyimides, the flexible copper clad foil plywood of liquid crystal polymer are used as base material (for example, see patent document 1 and 2).
But, the process that these methods need the laminating copper foil under high temperature (more than 300 DEG C) easily causes yield rate difference etc.
Problem, seeks to solve.
On the other hand, also exist copper foil covered folded obtained from the copper foil of low roughness is combined with polyimide layer
Plate come suppress from copper foil surface state conductor losses, suppress transmission loss method (for example, see patent document 3),
But the bonding process under high temperature (more than 300 DEG C) is stilled need when copper foil is fitted, easily causes the problems such as yield rate is poor, solution is sought
Certainly.
In addition, from the viewpoint of impedance control, the dielectric constant of preferred insulative material is relatively low.That is, the resistance of transmission circuit
Anti- (Z0) determined by the thickness and dielectric constant, the width of circuit and thickness of insulating materials.In recent years, the film of circuit substrate
Change promote, in order to take into account impedance control and filming, it is necessary to (1) reduction insulating materials dielectric constant or (2) circuit it is thin
Membranization and thin space.But, the possibility that circuit reliability is lost in (2) is high therefore not preferred.Therefore, in expanded circuit
In the sense that the free degree of design, the requirement of dielectric materials is high.
Prior art literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 08-058024 publications
Patent document 2：Japanese Unexamined Patent Application Publication 2014-526399 publications
Patent document 3：Japanese Unexamined Patent Publication 2015-91644 publications
The content of the invention
Invent problem to be solved
The major subjects of the present invention are to provide copper adhesivity, heat resistance, the low-k of insulating materials, low dielectric loss
It is new that the copper foil covered stack of angle tangent characteristic good and being lost using the copper foil covered stack with low transmission is characterized
Printed wiring board.
The means used to solve the problem
The result of the present inventor's further investigation finds, by being made dielectric film and copper foil layer via specific gluing oxidant layer
Copper foil covered stack obtained from folded, low dielectric property, heat resistance, metal adhesivity are excellent, and are folded using the metal-clad
The low transmission lossy for the printed wiring board that system is made is excellent, so as to complete the present invention.
That is, the present invention is as shown in following items 1~7.
A kind of 1. copper foil covered stacks of item, it is to possess to be layered at least unilateral of dielectric film (1) via gluing oxidant layer (2)
Face on copper foil (3) copper foil covered stack, it is characterised in that
The thermal coefficient of expansion of dielectric film (1) is 4~30ppm/ DEG C,
Gluing oxidant layer (2) contains anhydride group end polyimides (A) and crosslinking component (B), anhydride group end polyamides
Imines (A) is the reaction product of aromatic tetracarboxylic acid's acid anhydride and the diamine monomer comprising dimer type diamine,
10 mean roughness (Rz) in the face contacted with gluing oxidant layer (2) of copper foil (3) are 0.1~1.5 μm.
The copper foil covered stack of such as preceding paragraphes 1 of item 2., wherein, the content of dimer type diamine is 30 in diamine monomer
Mole more than %.
The copper foil covered stack of item 3. such as preceding paragraph 1 or preceding paragraphes 2, wherein, aromatic tetracarboxylic acid's acid anhydride is by following representations
Material.
(in formula, X represents singly-bound ,-SO2-、-CO-、-O-、-O-C6H4-C(CH3)2-C6H4- O- or-COO-Y-OCO- (Y tables
Show-(CH2)1- (1 represents 1~20) or-H2C-HC (- O-C (=O)-CH3)-CH2-。)。)
The 4. copper foil covered stack as any one of preceding paragraph 1~3 of item, wherein, crosslinking component (B) is selected from by polyphenyl
Ether resin, epoxy resin, benzoAt least one in the group that piperazine resin, bimaleimide resin and cyanate ester resin are constituted
Kind.
The 5. copper foil covered stack as any one of preceding paragraph 1~4 of item, wherein, gluing oxidant layer (2) is also containing reactivity
Polyglycidyl compounds (C).
The 6. copper foil covered stack as any one of preceding paragraph 1~5 of item, wherein, under the 10GHz of gluing oxidant layer (2)
Dielectric constant is less than 3.0, and dielectric loss angle tangent is less than 0.005.
A kind of 7. printed wiring boards of item, it is entered by the copper foil to the copper foil covered stack any one of preceding paragraph 1~6
Row wired circuit is processed and obtained.
Invention effect
According to the present invention it is possible to provide good with the adhesivity of copper foil, low dielectric property, low water absorbable, heat resistance are also excellent
It is good, therefore the high copper foil covered stack of reliability.Furthermore it is possible to manufacture dielectric by using the copper foil covered stack of the present invention
The low printed circuit board (PCB) of loss.The copper foil covered stack and printed circuit board (PCB) of the present invention is suitable for manufacture with smart mobile phone, mobile phone
For network associated electronic device, the mainframe computer such as the mobile communication equipment of representative or its base station apparatus, server/router etc.
Handle the multiwiring board of the product of high-frequency signal.
Embodiment
The copper foil covered stack of the present invention possesses at least unilateral face that dielectric film (1) is layered in via gluing oxidant layer (2)
On copper foil (3).The dielectric film (1) of the present invention is just not particularly limited as long as thermal coefficient of expansion is 4~30ppm/ DEG C, Ke Yilie
Citing is such as：Polyimides, PEI, aromatic polyamide, polyethylene terephthalate (PET), poly- naphthalene will be included
Material of film etc. is made in the composite of naphthalate (PEN), liquid crystal polymer or flexible epoxy/glass cloth etc..Heat
When the coefficient of expansion is less than 4ppm/ DEG C or thermal coefficient of expansion and is more than 30ppm/ DEG C, due to the thermal expansion system with the copper foil to be fitted
The difference of number (16~18ppm/ DEG C), can produce the problems such as warpage of layered product, adhesivity are reduced.Preferably 13~23ppm/
℃.In addition, specifically, from the viewpoint of heat resistance, dimensional stability, insulating properties, preferably polyimides.Need explanation
, the thermal coefficient of expansion in this specification refers to using thermo-mechanical analysis device (distance between chuck：20mm, coupons width
Degree：4mm, load：10mg, heating rate：10 DEG C/min of stretch mode) determine 100 DEG C~200 DEG C of value.
As described above, as dielectric film (1), polyimide film is optimal.Its preparation method can be using known manufacturer
Method.That is, using substantial equimolar one or more kinds of tetracarboxylic dianhydride's compositions and one or more diamines into
Point, it is polymerize in organic polar solvent, thus obtained polyamic acid polymer solution curtain coating is coated on glass plate, no
Become rusty on the supporters such as steel band, by part imidizate or partially dried (following to the polyamide acid film with self-supporting degree
Referred to as gel mould) peeled off from supporter, heating is further carried out after end is fixed using methods such as pin, clips so as to by polyamides
The complete imidizate of amino acid, thus obtains polyimide film.As commercially available polyimide film, it can enumerate：Japan's weaving strain
The XENOMAX (trade name) of formula commercial firm manufacture, the POMIRAN T (trade name) of Arakawa Chemical Industries, Ltd.'s manufacture, east are beautiful
The KAPTON (trade name) of Dupont Kabushiki Kaisha's manufacture, the UPILEX (trade name) of Ube Industries, Ltd's manufacture, strain formula meeting
Society Zhong Yuan Apical (trade name) etc..
The thickness of dielectric film (1) is not limited, preferably 5 μm~125 μm.Easiness, machinery particularly from making is special
Property from the viewpoint of, preferred thickness be 10 μm~75 μm, be preferably 10 μm~50 μm.
Gluing oxidant layer (2) is as long as containing anhydride group end polyimides (A) (hereinafter also referred to " (A) composition ") and being cross-linked into
(B) (hereinafter also referred to " (B) composition ") is divided just to be not particularly limited.(A) composition is preferably that aromatic tetracarboxylic acid's acid anhydride (a1) is (following
Also referred to as " (a1) composition ") and diamine monomer comprising dimer type diamine (a2) (hereinafter also referred to " (a2) composition ")
Reaction product, as long as above-mentioned reaction product, it is possible to without particular limitation using various known materials.
As (a1) composition, it can enumerate for example：Pyromellitic acid dianhydride, 4, the double O-phthalic acid dianhydrides of 4 '-oxygen, 3,3 ',
4,4 '-benzophenone tetracarboxylic dianhydride, 3,3 ', 4,4 '-diphenyl ether tetraformic dianhydride, 3,3 ', 4,4 '-diphenyl sulfone tetraformic acid two
Acid anhydride, 1,2,3,4- PMDAs, Isosorbide-5-Nitrae, 5,8- naphthalenetetracarbacidic acidic dianhydrides, 2,3,6,7- naphthalenetetracarbacidic acidic dianhydrides, 3,3 ', 4,4 '-
Bibenzene tetracarboxylic dianhydride, 2,2 ', 3,3 '-bibenzene tetracarboxylic dianhydride, 2,3,3 ', 4 '-bibenzene tetracarboxylic dianhydride, 2,3,3 ', 4 '-two
Benzophenone tetracarboxylic acid dianhydride, 2,3,3 ', 4 '-diphenyl ether tetraformic dianhydride, 2,3,3 ', 4 '-diphenyl sulfone tetraformic acid dianhydride, 2,2- are double
(3,3 ', 4,4 '-tetracarboxylic phenyl) tetrafluoropropane dianhydride, 2,2 '-bis- (3,4- di carboxyl phenyloxy phenyl) sulfone dianhydrides, 2,2- are double
Double (3, the 4- dicarboxyphenyi) propane dianhydrides and 4 of (2,3- dicarboxyphenyi) propane dianhydride, 2,2-, 4 '-[propane -2,2- diyl
Double (Isosorbide-5-Nitraes-Asia phenoxy group)] double O-phthalic acid dianhydrides etc., can one kind can also combine two or more.
From the viewpoint of solvent soluble, flexibility, adhesivity, heat resistance, (a1) composition is preferably by following formulas
The material of expression.
(in formula, X represents singly-bound ,-SO2-、-CO-、-O-、-O-C6H4-C(CH3)2-C6H4- O- or-COO-Y-OCO- (Y tables
Show-(CH2)1- (1 represents 1~20) or-H2C-HC (- O-C (=O)-CH3)-CH2-。)。)
(a2) composition be as derived from the dimeric dibasic acid of the dimer as unrighted acids such as oleic acid compound (referring to day
This Unexamined Patent 9-12712 publications etc.), can be without particular limitation using various known dimer type diamines.As
(a2) commercially available product of composition, can be enumerated for example：Versamine 551 (manufacture of BASF Amada Co., Ltd.s), Versamine
552 (BASF Amada Co., Ltd.s manufactures；Versamine 551 hydride), PRIAMINE1075, PRIAMINE1074 (
Manufactured for He great Amada Co., Ltd.s) etc., it can combine two or more.Hereinafter, one of hydrogenation dimer type diamine is shown.
From the viewpoint of solvent soluble, flexibility, adhesivity, heat resistance, the content of (a2) composition is preferably binary
30 moles of more than % in amine monomers.More preferably 50~100 moles %.
In (A) composition can as needed containing various known diamino polysiloxanes (hereinafter also referred to (a3) into
Point).Specifically, it can enumerate for example：α, ω-bis- (2- amino-ethyls) dimethyl silicone polymer, α, ω-bis- (3- aminopropans
Base) dimethyl silicone polymer, α, ω-bis- (4- aminobutyls) dimethyl silicone polymer, α, ω-bis- (5- Aminopentyls) poly- diformazan
Radical siloxane, α, ω-bis- [3- (2- aminophenyls) propyl group] dimethyl silicone polymer, α, ω-bis- [3- (4- aminophenyls) third
Base] dimethyl silicone polymer etc., can one kind can also combine two or more.
Can be (following to be also referred to as containing the diamine in addition to (a1) composition~(a3) composition as needed in (A) composition
For (a4) composition).Specifically, it can enumerate for example：Diaminocyclohexane, diamino-dicyclohexyl methane, 3,3 '-diformazan
Base -4,4 '-diamino-dicyclohexyl methane, 3,3 ', 5,5 '-tetramethyl -4,4 '-diamino-dicyclohexyl methane, 4,4 '-diamino
Base dicyclohexyl propane, the ring of diaminourea two [2.2.1] heptane, double (amino methyl) two ring [2.2.1] heptane, 3 (4), 8 (9)-bis-
The ester ring type binary such as (amino methyl) three ring [5.2.1.02,6] decane, 1,3- double aminomethyl cyclohexane, IPDs
Amine；Double amino such as 2,2- double [4- (3- amino-benzene oxygens) phenyl] propane, double [4- (4- amino-benzene oxygens) phenyl] propane of 2,2-
Phenoxyphenyl propane class；3,3 '-diaminodiphenyl ether, 3,4 '-diaminodiphenyl ether, 4, the diamino such as 4 '-diaminodiphenyl ether
Yl diphenyl ether class；The phenylenediamines such as p-phenylenediamine, m-phenylene diamine (MPD)；3,3 '-diamino diphenyl sulfide, 3,4 '-diaminourea hexichol
Base thioether, 4, the diamino diphenyl sulfide class such as 4 '-diamino diphenyl sulfide；3,3 '-diamino diphenyl sulfone, 3,4 '-two
Aminodiphenyl base sulfone, 4, the diamino diphenyl sulfone class such as 4 '-diamino diphenyl sulfone；3,3 '-diaminobenzophenone, 4,4 '-
Diaminobenzophenone, 3, the diaminobenzophenone class such as 4 '-diaminobenzophenone；3,3 '-diaminodiphenyl-methane, 4,
4 '-diaminodiphenyl-methane, 3, the diaminodiphenyl-methane class such as 4 '-diaminodiphenyl-methane；2,2- bis- (3- aminobenzenes
Base) diamino-phenyl such as propane, 2,2- bis- (4- aminophenyls) propane, 2- (3- aminophenyls) -2- (4- aminophenyls) propane
Propane class；2,2- bis- (3- aminophenyls) -1,1,1,3,3,3- HFC-236fa, 2,2- bis- (4- aminophenyls) -1,1,1,3,3,
3- HFC-236fas, 2- (3- aminophenyls) -2- (4- aminophenyls) -1, the diamino-phenyl hexafluoro such as 1,1,3,3,3- HFC-236fa
Propane class；1,1- bis- (3- aminophenyls) -1- diphenylphosphino ethanes, 1,1- bis- (4- aminophenyls) -1- diphenylphosphino ethanes, 1- (3- amino
Phenyl) the diamino-phenyl diphenylphosphino ethane class such as -1- (4- aminophenyls) -1- diphenylphosphino ethanes；1,3- double (3- amino-benzene oxygens) benzene,
Double amino such as 1,3- double (4- amino-benzene oxygens) benzene, Isosorbide-5-Nitrae-bis- (3- amino-benzene oxygens) benzene, Isosorbide-5-Nitrae-bis- (4- amino-benzene oxygens) benzene
Phenoxy group benzene class；1,3- double (3- amino benzoyls) benzene, 1,3- double (4- amino benzoyls) benzene, Isosorbide-5-Nitrae-bis- (3- aminobenzenes
Formoxyl) double amino benzoyl benzene classes such as benzene, Isosorbide-5-Nitrae-bis- (4- amino benzoyls) benzene；1,3- double (3- amino-α, alpha, alpha-dimethyl
Base benzyl) benzene, 1,3- double (4- amino-alpha, alpha-dimethylbenzyl) benzene, Isosorbide-5-Nitrae-bis- (3- amino-alpha, alpha-dimethylbenzyl) benzene, 1,
Double amino-dimethyl benzene classes such as double (4- amino-alpha, alpha-dimethylbenzyl) benzene of 4-；1,3- double (3- amino-α, α-two (fluoroforms
Base) benzyl) benzene, 1,3- double (4- amino-α, α-two (trifluoromethyl) benzyl) benzene, Isosorbide-5-Nitrae-bis- (3- amino-α, α-two (fluoroforms
Base) benzyl) double amino two (trifluoromethyl) benzyl benzene classes such as benzene, Isosorbide-5-Nitrae-bis- (4- amino-α, α-two (trifluoromethyl) benzyl) benzene；
2,6- double (3- amino-benzene oxygens) benzonitriles, double (3- amino-benzene oxygens) pyridines of 2,6-, 4,4 '-bis- (3- amino-benzene oxygens) connection
Benzene, 4, the amino-benzene oxygen biphenyl class such as 4 '-bis- (4- amino-benzene oxygens) biphenyl；It is double [4- (3- amino-benzene oxygens) phenyl] ketone, double
The aminophenoxy phenyl ketones such as [4- (4- amino-benzene oxygens) phenyl] ketone；It is double [4- (3- amino-benzene oxygens) phenyl] thioethers, double
The aminophenoxy phenyl thioether classes such as [4- (4- amino-benzene oxygens) phenyl] thioether；Double [4- (3- amino-benzene oxygens) phenyl] sulfones,
The aminophenoxy phenyl sulfone classes such as double [4- (4- amino-benzene oxygens) phenyl] sulfones；It is double [4- (3- amino-benzene oxygens) phenyl] ethers, double
The aminophenoxy phenyl ethers such as [4- (4- amino-benzene oxygens) phenyl] ether；2,2- double [4- (3- amino-benzene oxygens) phenyl] third
Double [3- (3- amino-benzene oxygens) phenyl] -1 of alkane, 2,2-, the double [4- (4- amino-benzene oxygens) of 1,1,3,3,3- HFC-236fa, 2,2-
Phenyl] -1, the aminophenoxy phenyl propane class such as 1,1,3,3,3- HFC-236fa；And double [the 4- (3- amino-benzene oxygens) of 1,3-
Benzoyl] benzene, 1,3- double [4- (4- amino-benzene oxygens) benzoyl] benzene, Isosorbide-5-Nitrae-bis- [4- (3- amino-benzene oxygens) benzoyls
Base] benzene, Isosorbide-5-Nitrae-bis- [4- (4- amino-benzene oxygens) benzoyl] benzene, 1,3- double [4- (3- amino-benzene oxygens)-α, alpha-alpha-dimethyl benzyl
Base] benzene, double [4- (the 4- amino-benzene oxygens)-alpha, alpha-dimethylbenzyl] benzene of 1,3-, Isosorbide-5-Nitrae-bis- [4- (3- amino-benzene oxygens)-α, α-
Dimethyl benzyl] benzene, Isosorbide-5-Nitrae-bis- [4- (4- amino-benzene oxygens)-alpha, alpha-dimethylbenzyl] benzene, 4,4 '-bis- [4- (4- aminobenzene oxygen
Base) benzoyl] diphenyl ether, 4,4 '-bis- [4- (4- amino-alpha, alpha-dimethylbenzyl) phenoxy group] benzophenone, 4,4 '-it is bis-
[4- (4- amino-alpha, alpha-dimethylbenzyl) phenoxy group] diphenyl sulfone, 4,4 '-bis- [4- (4- amino-benzene oxygens) phenoxy group] hexichol
Base sulfone, 3,3 '-diaminourea -4,4 '-two phenoxy benzophenones, 3,3 '-diaminourea -4,4 '-bigeminy phenoxy benzophenone, 3,
3 '-diaminourea -4- phenoxy benzophenones, 3,3 '-diaminourea -4- biphenylyloxies benzophenone, 6,6 '-bis- (3- aminobenzene oxygen
Base) -3,3,3, ' 3, '-tetramethyl -1,1 '-spirobindene is full, 6,6 '-bis- (4- amino-benzene oxygens) -3,3,3, ' 3, '-tetramethyl -
1,1 '-spirobindene is full, double (3- aminopropyls) tetramethyl disiloxanes of 1,3-, the double silica of (4- aminobutyls) tetramethyl two of 1,3-
Alkane, double (amino methyl) ethers, double (2- amino-ethyls) ethers, double (3- aminopropyls) ethers, double (2- aminomethoxies) ethyls] ether,
Double (aminomethoxy) ethane of double [2- (2- amino ethoxies) ethyl] ethers, double [2- (3- amino propoxyl group) ethyl] ethers, 1,2-,
1,2- double (2- amino ethoxies) ethane, double [2- (aminomethoxy) ethyoxyl] ethane of 1,2-, double [2- (the 2- amino second of 1,2-
Epoxide) ethyoxyl] ethane, double (3- aminopropyls) ethers of ethylene glycol, double (3- aminopropyls) ethers of diethylene glycol, triethylene glycol be double
(3- aminopropyls) ether, ethylenediamine, 1,3- diaminopropanes, 1,4-Diaminobutane, 1,5- 1,5-DAPs, 1,6- diaminourea
Hexane, 1,7- diaminoheptanes, 1,8- diamino-octanes, 1,9- diamino nonanes, 1,10- diamino decanes, 1,11- diaminourea
Hendecane, 1,12- diamino dodecanes etc., can be combined two or more.
(a1) composition (sour composition) and (a2) composition~(a4) composition (amine component) mol ratio [(a1)/[(a2)+(a3)+
(a4)]] it is not particularly limited, goes out from the viewpoint of the balance of adhesivity, heat-resisting adhesivity, flowing controlling and low dielectric property
Hair, typically about 0.9~about 1.25, preferably from about 0.9~about 1.15.
(a2) ratio of each composition in composition~(a4) composition is not particularly limited, from heat-resisting adhesivity, adhesivity, stream
From the viewpoint of the balance of dynamic controlling and low dielectric property, generally, [(a2)/[(a2)+(a3)+(a4)]] is about 10 moles of %
~about 100 moles of %, it is preferably from about 30 moles of %~about 100 mole %, [(a3)/[(a2)+(a3)+(a4)]] is about 0 to rub
Your %~about 50 mole %, it is preferably from about 0 mole of %~about 5 mole %, [(a4)/[(a2)+(a3)+(a4)]] is about 0 to rub
You are %~about 90 mole %, preferably from about 0 mole of %~about 70 mole %.
(A) composition can be manufactured by various known methods.For example, by (a1) composition and (a2) composition and according to
(a3) composition and (a4) composition needed to use enters at a temperature of normally about 60 DEG C~about 120 DEG C (preferably 80 DEG C~100 DEG C)
The sudden reaction of row normally about 0.1 hour~about 2 hours (preferably 0.1 hour~0.5 hour).Then, resulting addition polymerization is made
Product is further carried out about 0.5 hour~about 50 hours at a temperature of about 80 DEG C~about 250 DEG C, preferably 100 DEG C~200 DEG C
Imidization reaction, the i.e. dehydration closed-loop reaction of (preferably 1 hour~20 hours).In addition, during these reactions, can use
Solvent described later, particularly aprotic polar solvent are used as reaction dissolvent.
It should be noted that in imidization reaction, can use various known catalysts, dehydrating agent and after
The solvent stated.As catalysts, it can enumerate：The aromatic nitrile bases such as the aliphatic tertiary amine such as triethylamine class, dimethylaniline
Hetero ring type tertiary amines such as class, pyridine, picoline, isoquinolin etc., can be combined two or more., can be with addition, as dehydrating agent
Enumerate for example：Aromatic anhydrides such as the aliphatic anhydrides such as acetic anhydride, benzoyl oxide etc., can be combined two or more.
As reaction dissolvent, it can enumerate：METHYLPYRROLIDONE, DMA, gamma-butyrolacton, ring
Hexanone, hexahydrotoluene, toluene, dimethylbenzene, hexone, glycol dimethyl ether, diethylene glycol dimethyl ether, dipropyl two
The organic polar solvents such as alcohol dimethyl ether.These organic polar solvents can be used alone, and can also be used in mixed way a variety of.
(A) the imide ring closure rate of composition is not particularly limited, usually more than 70%, be preferably 85%~100%.
This, " imide ring closure rate " refers to the content (similarly hereinafter) of the cyclic imide key in (A) composition, can be for example, by NMR, IR points
The various spectrum means such as analysis are determined.
(A) physical property of composition is not particularly limited, from adhesivity, heat-resisting adhesivity, flowing controlling and low dielectric property
Balance from the viewpoint of, usual number-average molecular weight (refers to the polystyrene scaled value obtained using gel permeation chromatography.Under
It is together) about 5000~about 50000, (softening point refers to using commercially available analyzer (" ARES-2KSTD-FCO- softening point
STD ", Rheometric Scientfic companies manufacture) determine viscoplasticity distribution map in modulus of rigidity start reduction temperature.Under
It is about 30 DEG C~about 160 DEG C together).(A) concentration of the end anhydride group of composition is also not particularly limited, typically about 5000~about
20000eq/g。
For (A) composition, in order to show higher adhesivity, heat resistance, dielectric property, it will can change
(a1)~(a4) two or more (A) compositions after the species and ratio of composition are used in mixed way.The species number of (A) that is mixed
Amount, blending ratio are arbitrary.
(B) composition can be not particularly limited using various known materials.Wherein, from the sight of heat resistance, adhesivity
Point sets out, preferably polyphenylene oxide resin, epoxy resin, benzoPiperazine resin, bimaleimide resin and cyanate ester resin, its
In, from the viewpoint of dielectric property, the more preferably combination of polyfunctional epoxy resin and cyanate ester resin.
Polyphenylene oxide resin can be not particularly limited using various known polyphenylene oxide resins.Specifically, it is preferably
The polyphenylene oxide resin represented by following formulas.
(in formula, Z2Alkylidene or singly-bound that carbon number is 1~3 are represented, m represents that 0~20, n represents 0~20, m's and n
It is total to represent 1~30.)
It is not particularly limited as the characteristic of polyphenylene oxide resin, from the viewpoint of adhesive tension and low dielectric property, end
Hydroxyl concentration is that about 900~about 2500 μm of ol/g, number-average molecular weight are about 800~about 2000.
On epoxy resin, it can enumerate for example：Phenol novolak type epoxy resin, cresol novolak type epoxy tree
Fat, bisphenol A type epoxy resin, bisphenol f type epoxy resin, bisphenol-s epoxy resin, bisphenol-A epoxy resin, hydrogenation are double
Phenol F types epoxy resin, Stilbene-based epoxy resin, the epoxy resin of the skeleton containing triazine, the epoxy resin containing fluorene skeleton, chain
Aliphatic epoxy resin, alicyclic epoxy resin, glycidyl amine type epoxy resin, three oxybenzene methylmethane type epoxy resin, alkane
Base be modified three oxybenzene methylmethane type epoxy resin, biphenyl type epoxy resin, the epoxy resin of the skeleton containing dicyclopentadiene, containing naphthalene
The epoxy resin of skeleton, aryl alkene fundamental mode epoxy resin, four glycidyl group benzene dimethylamine, these epoxy resin are utilized two
Modified epoxy, dimer acid diglycidyl ester etc., can be combined two or more obtained from polyacids are modified.In addition, conduct
Commercially available product, can be enumerated for example：" jER828 ", " jER834 ", " jER807 " of Mitsubishi chemical Co., Ltd's manufacture,
" ST-3000 " of the manufacture of " jER630 ", Nippon Steel Chemical Co., Ltd, Daisel chemical industry Co., Ltd manufacture
" YD-172-X75 " of the manufacture of " Celloxide2021P ", Nippon Steel Chemical Co., Ltd etc..
Wherein, from the viewpoint of adhesivity, heat-resisting adhesivity and flowing controlling, the four of preferably following structures shrink sweet
Oil base benzene dimethylamine, the commercially available product such as " Tetrad-X " that Mitsubishi Gas Chemical Co., Ltd can be used to manufacture.
(in formula, Z3Represent phenylene or cyclohexenyl group.)
It should be noted that in the case of using epoxy resin, various known epoxy resin solidifications can be used together
Agent.Specifically, except various polyphenylene oxide resins described later, benzoPiperazine resin, bimaleimide resin and cyanate resin
Beyond fat, it can also enumerate：Succinic anhydride, phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic dianhydride, hexahydro are adjacent
Phthalate anhydride, 3- methylhexahydrophthalic anhydrides, 4- methylhexahydrophthalic anhydrides or 4- methyl hexahydro O-phthalics
The mixture of acid anhydrides and hexahydrophthalic anhydride, tetrabydrophthalic anhydride, methyl tetrahydrophthalic anhydride, nadic acid
Acid anhydride, methylnadic anhydride, norbornane -2,3- dicarboxylic acid anhydride, methyl norbornane -2,3- dicarboxylic acid anhydride, methylcyclohexene
The acid anhydride type curing agents such as dicarboxylic acid anhydride, 3- dodecenyl succinic anhydrides, octenyl succinic acid anhydride；Dicyandiamide (DICY), fragrance
Race's diamine (trade name " LonzacureM-DEA ", " LonzacureM-DETDA " etc..It is Long Sha Amada Co., Ltd.s system
Make), the amine curing agent such as aliphatic amine；Phenol resol resins, cresol novolac resin, bisphenol A-type novolaks tree
Fat, triazine modified phenol novolac resin, the trade name " SPH- of the phosphonitrile (Otsuka Chemical Co., Ltd manufacture of phenolic hydroxy group
100 " etc.) phenols curing agent, the cyclic phosphazene class compound such as；The rosin crosslinking agent such as maleic acid modified rosin or its hydride
Deng.Wherein, preferred cyanate ester resin.In addition, the usage amount of hardener for epoxy resin is not particularly limited, generally, relative to
The weight % of solid constituent 100 of the adhesive compound of the present invention, is about 0.1~about 50 weight %, preferably from about 1~about 40 weight
Measure %.
In addition, as hardener for epoxy resin, the polyphenylene ether compound represented by above-mentioned chemical formula 5 can also be used.
On benzoPiperazine resin, can be enumerated for example：6,6- (1- methyl ethylidene) it is double (3,4- dihydro -3- phenyl -
2H-1,3- benzoPiperazine), double (3,4- dihydro -3- methyl -2H-1, the 3- benzos of 6,6- (1- methyl ethylidene)Piperazine) etc., can
It is two or more to combine.It should be noted thatPhenyl, methyl, cyclohexyl etc. can be bonded on the nitrogen of piperazine ring.In addition, making
For commercially available product, it can enumerate for example：" the benzo of Shikoku Chem's manufacturePiperazine F-a types ", " benzoPiperazine P-d
Type ", " RLV-100 " of the manufacture of Air Water companies etc..
On bimaleimide resin, it can enumerate for example：4,4 '-diphenyl methane BMI, a sub- benzene
Base BMI, bisphenol-A diphenyl ether BMI, 3,3 '-dimethyl -5,5 '-diethyl -4,4 '-diphenyl
Methane BMI, 4- methyl isophthalic acids, 3- phenylenes BMI, 1,6 '-dimaleoyl imino-(2,2,4- tri-
Methyl) hexane, 4,4 '-diphenyl ether BMI, 4,4 '-diphenyl sulfone BMI etc. can combine two kinds
More than.In addition, as commercially available product, can enumerate such as " BAF-BMI " that JFE KCCs manufacture.
On cyanate ester resin, it can enumerate for example：2- chavicols cyanate, 4- metoxyphenols cyanate, 2,
Double (the 4- cyanatos phenol) -1 of 2-, 1,1,3,3,3- HFC-236fa, bisphenol A cyanate, diallyl bisphenol cyanate, 4- benzene
Base phenol cyanate, 1,1,1- tri- (4- cyanatophenyls) ethane, 4- cumyl phenols cyanate, 1,1- are double (4- cyanatophenyls)
Double (4- cyanatophenyls) propane of ethane, 4,4 '-bis-phenol cyanate and 2,2- etc., can be combined two or more.In addition, being used as city
Product are sold, can be enumerated for example：" PRIMASET BTP-6020S (manufacture of Long Sha Amada Co., Ltd.s) ", " PRIMASET PT-30
(manufacture of Long Sha Amada Co., Ltd.s) " etc..
Furthermore it is also possible to which curing catalysts are used together with (B) composition.Specifically, it can enumerate for example：1,8- bis-
Carbon -7- the alkene of azabicyclic [5.4.0] 11, triethylenediamine, benzyldimethylamine, 2,4, triethanolamine, dimethylaminoethanol,
The tertiary amines such as three (dimethylaminomethyl) phenol；
2-methylimidazole, 2- phenylimidazoles, 2- phenyl -4-methylimidazole, 2-ethyl-4-methylimidazole, 1- cyanoethyls -2-
The imidazoles such as undecyl imidazole, 2- heptadecyl imidazoles；
Organic phosphines such as tributylphosphine, methyldiphenyl base phosphine, triphenylphosphine, diphenylphosphine, Phenylphosphine；
TetraphenylTetraphenyl borate salts, 2-ethyl-4-methylimidazole tetraphenyl borate salts, N-methylmorpholine tetraphenyl boron
The tetraphenyl boron salt such as hydrochlorate；Zn, Cu and Fe's of the organic acids such as octanoic acid, stearic acid, acetylacetone,2,4-pentanedione, aphthenic acids and salicylic acid etc. has
Machine metal salt；
Benzoyl peroxide, methyl ethyl ketone peroxide, cyclohexanone peroxide, lauroyl peroxide, di-tert-butyl peroxide,
Radical initiators such as peroxidized t-butyl perbenzoate, cumene hydroperoxide, dicumyl peroxide etc.；
It can combine two or more.In addition, the usage amount of the catalyst is not particularly limited, generally, by the present invention's
It is about 0.01~about 5 weight % when the solid constituent of adhesive compound is set to 100 weight %.
(B) usage amount of composition is not particularly limited, generally, relative to the parts by weight of (A) composition 100, by solid constituent weight
Amount is scaled about 3~about 30 parts by weight, is preferably from about 5~about 15 parts by weight.
It can contain in addition to above-mentioned (A) composition and (B) composition in the adhesive compound for forming gluing oxidant layer (2)
Organic solvent., can be without particular limitation using various known solvents as organic solvent.It is used as concrete example, Ke Yilie
Citing is such as：METHYLPYRROLIDONE, dimethylformamide, dimethyl acetamide, dimethyl sulfoxide (DMSO), N- methyl caprolactams,
The ester ring type such as the aprotic polar solvents such as TRIGLYME, diethylene glycol dimethyl ether, cyclohexanone, hexahydrotoluene solvent,
The fragrance such as the alcohols solvents such as methanol, ethanol, propyl alcohol, phenmethylol, cresols, toluene same clan solvent etc., can be combined two or more.
Can coordinate as needed in the adhesive compound for forming gluing oxidant layer (2) esterification by ring opening catalysts,
Dehydrating agent, plasticizer, weather resisting agent, antioxidant, heat stabilizer, lubricant, antistatic agent, brightening agent, colouring agent, conductive agent,
Releasing agent, surface conditioning agent, viscosity modifier, phosphonium flame retardant, fire-retardant filler, silica filler and fluorine-containing filler etc. are added
Agent.
Adhesive compound can also containing reactive polyglycidyl compounds (C) (hereinafter also referred to (C) into
Point.).As (C) composition, it is not particularly limited, can enumerates for example by formula：Q-Si(R1)a(OR2)3-a(in formula, Q represents bag
Group containing the functional group reacted with anhydride group, R1It is 1~8 alkyl, R to represent hydrogen or carbon number2It is 1 to represent carbon number
~8 alkyl, a represents 0,1 or 2) silyl compound of expression etc..It is used as reactive functional groups contained in Q, Ke Yilie
Lift amino, epoxy radicals and sulfydryl etc..
(C) composition is utilized, can be adjusted while the low dielectric property of cured layer of adhesive of the present invention is kept
Save its melt viscosity.As a result it can press down while interfacial adhesion (the so-called anchoring effect) of the cured layer and base material is improved
Make oozing out and (operation being referred to as flowing control sometimes below) from the cured layer of base material end generation.
As the compound that the functional group in Q is amino, it can enumerate for example：N-2- (amino-ethyl) -3- aminopropyls
Methyl dimethoxysilane, N-2- (amino-ethyl) -3- TSL 8330s, 3- aminopropyl trimethoxy silicon
Alkane, APTES and 3- ureidopropyltrialkoxysilanes etc..
As the compound that the functional group in Q is epoxy radicals, it can enumerate for example：2- (3,4- epoxycyclohexyl) ethyl three
Methoxy silane, 3- glycidoxypropyls dimethoxysilane, 3- glycidoxypropyltrime,hoxysilanes, 3- rings
Oxygen propoxypropyl methyldiethoxysilane and 3- glycidoxypropyl group triethoxysilanes etc..
As the compound that the functional group in Q is sulfydryl, it can enumerate for example：3-mercaptopropyi trimethoxy silane, 3-
Mercaptopropyltriethoxysilane, 3- mercaptopropyis methyl dimethoxysilane and 3- mercaptopropyi methyldiethoxysilanes
Deng.
Dielectric constant under the 10GHz of gluing oxidant layer (2) is not particularly limited, and usually less than 3.0, dielectric loss angle is just
Cut preferably less than 0.005.Thus, copper foil covered stack of the invention can be suitable for suppressing transmission loss.More preferably
It is that dielectric constant is 1.5~2.9, dielectric loss angle tangent is less than 0.0005~0.004.
10 mean roughness (Rz) in the face contacted with gluing oxidant layer (2) of copper foil (3) are as long as 0.1 μm~1.5 μm
Just it is not particularly limited, such as rolled copper foil, electrolytic copper foil can be enumerated.So-called 10 mean roughness (Rz) refer to herein
The average value from the up to absolute altitude on the 5th high mountain top is represented with micron in the part that datum length is extracted from cross section curve
And from most deep to the absolute altitude of the 5th deep the lowest point average value difference value.In addition, its thickness is also not particularly limited, it is usually
About 1 μm~about 100 μm, preferably from about 2 μm~about 38 μm.In addition, the copper foil can be implement it is various surface treatment it is (coarse
Change, antirust etc.) after copper foil.As antirust treatment, it can enumerate at the plating using the plating solution containing Ni, Zn, Sn
The so-called mirror-polishing processing such as reason, chromic acid salt treatment.
The copper foil covered stack of the present invention is obtained in the following way：Above-mentioned adhesive compound is coated on into base material to go forward side by side
Row drying and the gluing oxidant layer (2) for forming the state of being uncured or partially cured, another base material of then fitting, then to adhesive
Layer (2) carries out solidify afterwards.The base material of coating binder composition and the base material fitted afterwards can be dielectric film (1), copper foil (3)
Any one of.
The coating method of gluing oxidant layer (2) can use brushing, dip-coating, spraying, comma scraper coating, blade coating, mouth mold formula
The methods such as coating, die lip coating, roller coat, curtain coating.
Drying means can be used at preferably 40 DEG C~250 DEG C, more preferably 70 DEG C~170 DEG C, about 2 minutes~about 15 minutes
Under conditions of pass through the methods of the stoves such as heated-air drying, FAR INFRARED HEATING, high-frequency induction heating.
Applying method can be used carries out layer of rolls at a temperature of preferably 40 DEG C~250 DEG C, more preferably 50 DEG C~200 DEG C
Pressure, the method for hot pressing.
Solidify afterwards can use 120 degree~250 degree temperature, preferably 70 DEG C~200 DEG C, about 30 minutes~about 48 hours
Under conditions of pass through the methods of the stoves such as heated-air drying, FAR INFRARED HEATING, high-frequency induction heating.
In view of adhesivity, heat resistance, the easiness of coating, the danger of dissolvent residual, the thickness of gluing oxidant layer (2) is excellent
Elect about 1 μm~about 70 μm as.
It is also the present invention by the printed circuit board obtained from the copper-clad surface of copper foil covered stack formation circuit pattern
One of.As the method for forming circuit pattern, such as subtractive process, semi-additive process can be enumerated.As semi-additive process, it can enumerate
Such as following method：The copper-clad surface of the copper foil covered stack of the present invention is patterned using resist film, electricity is then carried out
Copper facing, removes resist, and be etched using alkali lye.In addition, the thickness of the circuit pattern layer in the printed wiring board does not have
It is particularly limited to.
Embodiment
Hereinafter, the present invention is specifically illustrated by embodiment and comparative example, but the scope of the present invention is not by it
Limit.In addition, in each example, unless otherwise specified, part and % are weight basis.It should be noted that number-average molecular weight
It is the value obtained using commercially available measuring machine (" HLC-8220GPC ", TOSOH Co., Ltd manufacture), in addition, glass transition temperature
Degree is the value obtained using commercially available analyzer (" DSC6200 ", Seiko instrument Co., Ltd. manufacture).
<(A) the nonvolatile component content of composition>
The solution 1g of (A) composition is weighed, is dried 60 minutes using 180 DEG C of circulated air drying machines, before and after drying
Weight, nonvolatile component content is calculated using formula 1.
(formula 1)=(dried weight (g))/(weight (g) before drying) × 100 (%)
Production Example 1
In the reaction vessel for possessing mixer, water knockout drum, thermometer and nitrogen ingress pipe, commercially available aromatic series four is put into
Carboxylic acid dianhydride (trade name " BTDA-UP ", the manufacture of Ying Chuan Amada Co., Ltd.s；3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride
Content be more than 99.8%) 210.0g, cyclohexanone 1008.0g, hexahydrotoluene 201.6g, solution is heated to 60 DEG C.Then,
Dropwise addition hydrogenation dimer type diamine (trade name " PRIAMINE 1075 ", the manufacture of He great Amada Co., Ltd.s) 341.7g, then
Imidization reaction was carried out with 10 hours at 140 DEG C, thus obtains that softening point is about 80 DEG C and weight average molecular weight is 35,000
The solution (nonvolatile component content 33.9%) of polyimide resin (A-1).It should be noted that in whole diamine monomers
The content of dimer type diamine is 100 moles of %, and the mol ratio of sour composition/amine component is 1.03.
Production Example 2
In the reaction vessel same with Production Example 1, commercially available aromatic tetracarboxylic acid's dianhydride (trade name is put into
" BisDA1000 ", Ying Chuan Amada Co., Ltd.s manufacture；The adjacent benzene of 4,4 '-[propane -2,2- diyl is double (Isosorbide-5-Nitrae-phenylene epoxide)] two
The content of diformazan acid dianhydride is 98.0%) 297.8g, cyclohexanone 818.95g, hexahydrotoluene 136.49g, and solution is heated to
60℃.Then, the double aminomethyl cyclohexane 24.83g of the 200.28g of PRIAMINE 1075 and 1,3- are added dropwise, then 140 DEG C with
Carry out imidization reaction within 10 hours, thus obtain the polyimides that softening point is about 100 DEG C and weight average molecular weight is 28,000
(A-2) solution (nonvolatile component content 32.2%).It should be noted that the dimer type binary in whole diamine monomers
The content of amine is 68 moles of %, and the mol ratio of sour composition/amine component is 1.05.
Production Example 3
In the reaction vessel for possessing mixer, water knockout drum, thermometer and nitrogen ingress pipe, commercially available aromatic series four is put into
Carboxylic acid dianhydride (trade name " BisDA1000 ", the manufacture of Ying Chuan Amada Co., Ltd.s；4, the 4 '-[double (Isosorbide-5-Nitraes-Asia of propane -2,2- diyl
Phenyl epoxide)] contents of two O-phthalic acid dianhydrides is 98.0%) 200.00g, cyclohexanone 700.00g, hexahydrotoluene
175.00g, 60 DEG C are heated to by solution.Then, hydrogenation dimer type diamine (trade name " PRIAMINE 1075 ", standing grain is added dropwise
Big Amada Co., Ltd.'s manufacture) 190.54g, imidization reaction then was carried out with 10 hours at 140 DEG C, softening point is thus obtained
It is the solution (nonvolatile component content 30.2%) for the polyimide resin (A-3) that about 80 DEG C and weight average molecular weight are 22,000.
It should be noted that the content of the dimer type diamine in whole diamine monomers is 100 moles of %, sour composition/amine component
Mol ratio be 1.03.
Production Example 4
In the reaction vessel same with Production Example 1, commercially available aromatic tetracarboxylic acid's dianhydride (trade name " BTDA- is put into
PF ", the manufacture of Ying Chuan Amada Co., Ltd.s；3,3 ', 4, the content of 4 '-benzophenone tetracarboxylic dianhydride is 98%) 190.0g, hexamethylene
Ketone 277.5g, hexahydrotoluene 182.4g, 60 DEG C are heated to by solution.Then, PRIAMINE 1075277.5g and α is added dropwise,
ω-bis- (3- aminopropyls) dimethyl silicone polymer (trade name " KF-8010 ", Shin-Etsu Chemial Co., Ltd's manufacture)
23.8g, then carried out imidization reaction at 140 DEG C with 10 hours, and it is about 70 DEG C and weight average molecular weight thus to obtain softening point
For the solution (nonvolatile component content 30.8%) of 18,000 polyimides (A-4).It should be noted that whole diamine lists
The content of dimer type diamine in body is that 95 moles of %, the mol ratio of sour composition/amine component are 1.09.
Coordinating example 1
By the solution 10.20g of (A-1) composition, the solution 10.74g of (A-2) composition, the solution 5.72g of (A-3) composition, work
For the N of (B) composition, N- diglycidyl -4- glycidyl-oxyanilines (trade name " jER630 ", Mitsubishi Chemical's strain formula
Commercial firm manufactures) methyl ethyl ketone solution of 0.27g and cyanate ester resin (trade name " TA ", the manufacture of gas Co., Ltd. of Mitsubishi Chemical)
(nonvolatile component content 40%) 0.48g, N-2- (amino-ethyl) -3- TSL 8330s (trade name " KBM-
603 ", Shin-Etsu Chemial Co., Ltd manufacture) toluene solution (nonvolatile component content 10%) 0.18g, as dilute it is molten
The toluene 2.81g mixing of agent, so as to obtain the adhesive compound that nonvolatile component content is 30.0%.It should be noted that
(A) content of the dimer type diamine in the whole diamine monomers used in composition synthesis is 87.2 moles of %.
Coordinating example 2~13, compare coordinating example 1
Adhesive compound has been obtained with the composition shown in table 1 or table 2.
Compare coordinating example 2
Adhesive compound is used as using carboxyl NBR (trade name " XER-32C ", JSR Corp. manufacture).
Compare coordinating example 3
Adhesive group is used as using acrylic elastomer (trade name " SG-708-6 ", Nagase chemical Co., Ltd manufacture)
Compound.
<The making of copper foil covered stack>
Embodiment 1~13, comparative example 1~3
Coordinating example 1~13 is coated on rolling copper with the adhesive compound for comparing coordinating example 1~3 using gap coating machine
Paper tinsel (trade name " GHF5 ", the manufacture of JX metals Co., Ltd., 10 mean roughness (Rz)：0.45 μm) cause dried thickness
For 12 μm, then dried 10 minutes at 150 DEG C, thus obtain the copper foil of resin.Using the copper foil of the two panels resin, with glue
Stick face is the mode of inner side, is clipped in the polyimide film (trade name " KAPTON after carrying out dehumidifying in 10 minutes at 120 DEG C
100EN ", the manufacture of Dong Li Dupont Kabushiki Kaisha；25 μm of thickness；Thermal coefficient of expansion；15ppm/ DEG C) between, under 170 DEG C, 3MPa
30 minutes heat laminations are carried out, copper foil covered stack is thus obtained.
Comparative example 4
As the copper foil covered stack of not gluing oxidant layer, the R-F705 that Panasonic manufactures has been used (in Kuraray strain formula meeting
The LCP " Vecstar " of the society's manufacture two-sided material obtained from 300 DEG C of laminated rolled copper foils).
Comparative example 5
As the copper foil covered stack of not gluing oxidant layer, the R-F775 that Panasonic manufactures has been used (in the emerging production strain formula in space portion
The polyimides " Upilex-VT " of commercial firm's manufacture is (by thermoplastic polyimide layer/non-thermal plasticity polyimide layer/thermoplastic poly
Three layers of imide layer composition) the two-sided material obtained from 300 DEG C of laminated rolled copper foils).
<The dielectric constant of gluing oxidant layer and the measure of dielectric loss angle tangent>
To fluorine resin PFA square positions (diameter 75mm, Sogo Corporation's Physicochemical nitre make manufactured) injection about 7g
The adhesive compound of coordinating example 1~13,30 DEG C × 10 hours, 70 DEG C × 10 hours, 100 DEG C × 6 hours, it is 120 DEG C × 6 small
When, 150 DEG C × 6 hours, solidified under conditions of 180 DEG C × 12 hours, thus obtain the solidfied material piece of about 300 μm of thickness.
Then, commercially available Dielectric Coefficient device (cavity resonator type, AET systems are used according to JIS C2565 to the solidfied material piece
Make) determine 10GHz under dielectric constant and dielectric loss angle tangent.The physics value for comparing coordinating example 1~5 with reference to catalogue
Value.Result (similarly hereinafter) is shown in Tables 1 and 2.
<Adhesive test>
To the copper foil covered stack of embodiment 1~13, according to JIS C-6481, (flexible printing wiring board is folded with copper foil covered
Plate test method) determine peel strength (N/mm).The physics value of comparative example with reference to catalogue value.
<Solder heat resistance is tested>
For embodiment 1~13 and the copper foil covered stack of comparative example 1~5, with copper in 288 DEG C of solder bath after solidification
Paper tinsel laterally under mode suspend 30 seconds, confirmation whether there is cosmetic variation.Situation without change is determined as zero, there will be foaming,
The situation of expansion is determined as ×.
<The making of circuit evaluation printed wiring board>
To embodiment 1~13 and the copper foil covered stack of comparative example 1~5, Resist patterns is formed.Then, dipping is passed through
Copper foil is etched in the ferric chloride in aqueous solution of concentration 40%, the copper circuit that line length is 10cm is thus produced.
<Transmission loss is determined>
For embodiment 1~13 and the circuit evaluation printed wiring board of comparative example 1~5, network analyser (commodity are used
Name " E8363B ", Keysight Technologies manufactures), make impedance consistent with 50 Ω, determine 10GHz insertion (transmission)
S21 is lost.
[table 2]
The usage amount of each composition in ※ tables shows (unit strictly according to the facts：g).
※1：(A) weight average molecular weight of composition：(A-1)-35000、(A-2)-28000、(A-3)-22000、(A-4)-
18000
※2：The manufacture of GHF5-JX metals Co., Ltd., 10 mean roughness (Rz)：0.45μm
BHFX changes the manufacture of-JX metals Co., Ltd., 10 mean roughness (Rz)：0.90μm
※3：The dielectric constant and dielectric loss angle tangent of gluing oxidant layer are shown in embodiment 1~13.
Claims (7)
1. a kind of copper foil covered stack, it is to possess to be layered at least unilateral face of dielectric film (1) via gluing oxidant layer (2)
Copper foil (3) copper foil covered stack, it is characterised in that
The thermal coefficient of expansion of dielectric film (1) is 4~30ppm/ DEG C,
Gluing oxidant layer (2) contains anhydride group end polyimides (A) and crosslinking component (B), anhydride group end polyimides
(A) it is the reaction product of aromatic tetracarboxylic acid's acid anhydride and the diamine monomer comprising dimer type diamine,
10 mean roughness (Rz) in the face contacted with gluing oxidant layer (2) of copper foil (3) are 0.1 μm~1.5 μm.
2. copper foil covered stack as claimed in claim 1, wherein, the content of dimer type diamine is in diamine monomer
30 moles of more than %.
3. copper foil covered stack as claimed in claim 1 or 2, wherein, aromatic tetracarboxylic acid's acid anhydride is represented by following formulas
Material,
In formula, X represents singly-bound ,-SO2-、-CO-、-O-、-O-C6H4-C(CH3)2-C6H4- O- or-COO-Y-OCO-,
Y represents-(CH2)l- or-H2C-HC (- O-C (=O)-CH3)-CH2-,
L represents 1~20.
4. such as copper foil covered stack according to any one of claims 1 to 3, wherein, crosslinking component (B) is selected from by polyphenylene oxide
Resin, epoxy resin, benzoAt least one of group that piperazine resin, bimaleimide resin and cyanate ester resin are constituted.
5. such as copper foil covered stack according to any one of claims 1 to 4, wherein, gluing oxidant layer (2) is also containing reactive alkane
Epoxide silyl compound (C).
6. such as copper foil covered stack according to any one of claims 1 to 5, wherein, Jie under the 10GHz of gluing oxidant layer (2)
Electric constant is less than 3.0, and dielectric loss angle tangent is less than 0.005.
7. a kind of printed wiring board, it is carried out by the copper foil to copper foil covered stack according to any one of claims 1 to 6
Wired circuit is processed and obtained.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016000423 | 2016-01-05 | ||
| JP2016-000423 | 2016-01-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107009697A true CN107009697A (en) | 2017-08-04 |
Family
ID=59306122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710008965.9A Pending CN107009697A (en) | 2016-01-05 | 2017-01-05 | Copper foil covered stack and printed wiring board |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP6825368B2 (en) |
| KR (1) | KR20170082130A (en) |
| CN (1) | CN107009697A (en) |
| TW (1) | TWI716524B (en) |
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| CN110871606A (en) * | 2018-09-03 | 2020-03-10 | 日铁化学材料株式会社 | Metal-clad laminate, adhesive sheet, adhesive polyimide resin composition, and circuit board |
| CN111040156A (en) * | 2019-11-28 | 2020-04-21 | 李南文 | Solvent-resistant and high-dimensional-stability cross-linked polyimide film |
| CN111303424A (en) * | 2020-04-15 | 2020-06-19 | 江阴骏驰新材料科技有限公司 | Transparent high polymer material composition and application thereof |
| CN111836716A (en) * | 2018-03-30 | 2020-10-27 | 三井金属矿业株式会社 | Copper-clad laminated board |
| CN112048240A (en) * | 2019-06-06 | 2020-12-08 | 达迈科技股份有限公司 | Primer composition, metal laminate and method for producing the same |
| CN113043690A (en) * | 2019-12-27 | 2021-06-29 | 日铁化学材料株式会社 | Metal-clad laminate and circuit board |
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| US10767051B2 (en) | 2016-09-29 | 2020-09-08 | Sekisui Chemical Co., Ltd. | Cured body and multilayered substrate |
| JP2018140544A (en) * | 2017-02-28 | 2018-09-13 | 新日鉄住金化学株式会社 | Metal-clad laminate, adhesive sheet, adhesive polyimide resin composition, and circuit board |
| TWI637405B (en) * | 2017-03-15 | 2018-10-01 | 臻鼎科技股份有限公司 | Low dielectric resin composition, film and circuit board using the same |
| JP7271146B2 (en) | 2017-12-28 | 2023-05-11 | 日鉄ケミカル＆マテリアル株式会社 | Dimer diamine composition, method for producing the same, and resin film |
| JP7203409B2 (en) * | 2018-10-25 | 2023-01-13 | ユニチカ株式会社 | Bismaleimide |
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| JP7302461B2 (en) * | 2019-12-10 | 2023-07-04 | トヨタ紡織株式会社 | Polyamide compound and method for producing the same |
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| KR20230159374A (en) * | 2021-03-25 | 2023-11-21 | 니폰 가야꾸 가부시끼가이샤 | Resin compositions, cured products, resin sheets, prepregs, metal foil-clad laminates, multilayer printed wiring boards, sealing materials, fiber-reinforced composite materials, adhesives, and semiconductor devices. |
| CN113677089B (en) * | 2021-08-11 | 2023-03-10 | 华为技术有限公司 | Printed circuit board, antenna system and electronic equipment |
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| CN111836716A (en) * | 2018-03-30 | 2020-10-27 | 三井金属矿业株式会社 | Copper-clad laminated board |
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| CN112048240A (en) * | 2019-06-06 | 2020-12-08 | 达迈科技股份有限公司 | Primer composition, metal laminate and method for producing the same |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2017121807A (en) | 2017-07-13 |
| KR20170082130A (en) | 2017-07-13 |
| JP6825368B2 (en) | 2021-02-03 |
| TWI716524B (en) | 2021-01-21 |
| TW201736118A (en) | 2017-10-16 |
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Application publication date: 20170804 |