CN106977716A - Resin combination, adhesive, membranaceous adhesive material, sheet adhesive, the copper foil of resin, copper-clad laminated board, wiring plate - Google Patents
Resin combination, adhesive, membranaceous adhesive material, sheet adhesive, the copper foil of resin, copper-clad laminated board, wiring plate Download PDFInfo
- Publication number
- CN106977716A CN106977716A CN201610874044.6A CN201610874044A CN106977716A CN 106977716 A CN106977716 A CN 106977716A CN 201610874044 A CN201610874044 A CN 201610874044A CN 106977716 A CN106977716 A CN 106977716A
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- Prior art keywords
- composition
- adhesive
- resin combination
- resin
- double
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 106
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 106
- 229920005989 resin Polymers 0.000 title claims abstract description 85
- 239000011347 resin Substances 0.000 title claims abstract description 85
- 239000000463 material Substances 0.000 title claims abstract description 44
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 239000011889 copper foil Substances 0.000 title claims abstract description 31
- -1 polysiloxane Polymers 0.000 claims abstract description 88
- 229920001721 polyimide Polymers 0.000 claims abstract description 41
- 239000004642 Polyimide Substances 0.000 claims abstract description 30
- 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 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 28
- 150000004985 diamines Chemical class 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 239000000539 dimer Substances 0.000 claims abstract description 16
- 239000012790 adhesive layer Substances 0.000 claims abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 7
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 212
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 239000009719 polyimide resin Substances 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000004026 adhesive bonding Methods 0.000 claims description 9
- 150000008064 anhydrides Chemical group 0.000 claims description 8
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
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- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
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- 229920006380 polyphenylene oxide Polymers 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 7
- 150000000000 tetracarboxylic acids Chemical class 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 62
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 51
- 238000004519 manufacturing process Methods 0.000 description 49
- 239000002585 base Substances 0.000 description 33
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 30
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- 230000000052 comparative effect Effects 0.000 description 20
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
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- 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 10
- 229910052802 copper Inorganic materials 0.000 description 10
- 239000010949 copper Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 150000008065 acid anhydrides Chemical class 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
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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 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical group 0.000 description 5
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 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 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 239000000654 additive Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- 150000001642 boronic acid derivatives Chemical class 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
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical class C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-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
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- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 2
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- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000012777 electrically insulating material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 description 1
- QSCNLGHKALSYKF-UHFFFAOYSA-N ethoxymethanamine Chemical compound CCOCN QSCNLGHKALSYKF-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical class NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical class NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 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
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-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
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical class OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 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
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000012453 solvate Substances 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
- 229940014800 succinic anhydride Drugs 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 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
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical class NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
- C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
-
- 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
- H05K1/0296—Conductive pattern lay-out details not covered by sub groups H05K1/02 - H05K1/0295
- H05K1/0298—Multilayer circuits
-
- 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
-
- 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
- H05K1/14—Structural association of two or more printed circuits
- H05K1/144—Stacked arrangements of planar printed circuit boards
-
- 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
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/38—Improvement of the adhesion between the insulating substrate and the metal
- H05K3/386—Improvement of the adhesion between the insulating substrate and the metal by the use of an organic polymeric bonding layer, e.g. adhesive
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
- C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2479/00—Presence of polyamine or polyimide
- C09J2479/08—Presence of polyamine or polyimide polyimide
-
- 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
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/01—Dielectrics
- H05K2201/0137—Materials
- H05K2201/0154—Polyimide
Abstract
The present invention relates to resin combination, adhesive, membranaceous adhesive material, sheet adhesive, the copper foil of resin, copper-clad laminated board, wiring plate.The present invention, which is provided, can form the new type polyimide class adhesive of adhesivity, heat resistance and the good adhesive layer of low dielectric property.A kind of resin combination, it, which is included, makes aromatic tetracarboxylic acid dianhydride (a1) of the content containing free carboxy acid less than 1 weight % and hydrogenates dimer diamine (a2) and be free of polyimides (A1) formed by monomer group (1) reaction of diamino polysiloxane (a3).
Description
Technical field
The present invention relates to resin combination, adhesive, membranaceous adhesive material, sheet adhesive, multiwiring board, resin copper
Paper tinsel, copper-clad laminated board 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 it is logical in the movable type such as mobile phone, smart mobile phone using the multiwiring board of above-mentioned plate
Obtained extensively in the products such as news network associated electronic device, the mainframe computer such as equipment or its base station apparatus, servomechanism/router
Use.
In recent years, in these products, in order to transmit, handle the information of Large Copacity at high speed, the telecommunications of high frequency has been used
Number, but high-frequency signal is very easy to decay, therefore, is also required that for above-mentioned multiwiring board and suppresses to transmit setting for loss as far as possible
Meter.
As the means of the transmission loss suppressed in multiwiring board, for example, in stacking printed wiring board or printed circuit
During plate, it is considered to certainly excellent but also with relative dielectric constant and dielectric loss angle tangent small characteristic using adhesive tension
The dielectric materials of (hereinafter also referred to low dielectric property).
As the adhesive compound that can be used as dielectric materials, comprising making aromatic tetracarboxylic acid's dianhydride and dimerization
The polyimide adhesive of the crosslinking agent such as polyimides, epoxy resin formed by diamine reactant and organic solvent is public
(the referenced patent document 1) known, but low dielectric property is sometimes insufficient.
On the other hand, as the excellent polyimide adhesive of low dielectric property, comprising making aromatic tetracarboxylic acid's dianhydride
With the polyimides of the crosslinking agent such as polyimides, epoxy resin and organic solvent formed by diamino polysiloxane reaction
Class adhesive is known (referenced patent document 2), but in the cognitive scope of the applicant, low dielectric property is insufficient.
Prior art literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 2013-199645 publications
Patent document 2：Japanese Unexamined Patent Publication 7-154042 publications
The content of the invention
Invent problem to be solved
The major subjects of the present invention, which are to provide, can form adhesivity, heat resistance and the good adhesive layer of low dielectric property
New type polyimide class adhesive.
Method for solving problem
Present inventor has performed the glue for further improving the polyimide adhesive described in patent document 1 and 2
The research of viscous force and dielectric property.
First, it is conceived in aromatic tetracarboxylic acid's dianhydride and actually contains the free carboxy acid from raw material as impurity.
It is then assumed that：The carboxyl of the free carboxy acid directly improves the polarity of polyimides, the main cause of the moisture absorption as polyimides,
As a result, the low dielectric property of adhesive is deteriorated.
In addition, being also conceived to the structure of dimer diamine.Establish following hypothesis：Dimer diamine is typically by being used as oleic acid etc.
Polymer derived from the dimeric dibasic acid of the dimer of unrighted acid (with reference to Japanese Unexamined Patent Publication 9-12712 publications etc.), is dividing
Contain a large amount of conjugated double bonds in sub, these pi-electrons improve the polarity of polyimides, as a result, the low dielectric property of adhesive becomes
It is insufficient.
In addition, new discovery：Diamino polysiloxane with dimer diamine in the case where being applied in combination, to polyimides
Low dielectric loss angle tangent has a negative impact.Its reason is still not clear, but thinks the surface energy possibly due to polysiloxanes
Greatly repulsion is produced with the polar group (imide etc.) in polyimides.
The present invention is completed based on research above.That is, the present invention relates to following resin combinations, adhesive, membranaceous glue
Viscous material, sheet adhesive, multiwiring board, the copper foil of resin, copper-clad laminated board and printed wiring board.
1. a kind of resin combination, it includes the aromatic tetracarboxylic acid for making the content containing free carboxy acid be less than 1 weight %
Dianhydride (a1) and hydrogenation dimer diamine (a2) and without diamino polysiloxane (a3) monomer group (1) reaction formed by polyamides
Imines (A1).
2. the resin combination of item 1 as described above, wherein, aromatic tetracarboxylic acid's dianhydride of (a1) composition is constituted by following structures
Represent.
(in formula, X represents singly-bound ,-SO2-、-CO-、-O-、-O-C6H4-C(CH3)2-C6H4- O- or-COO-Y-OCO- (Y tables
Show-(CH2)l- (l=1~20) or-H2C-HC (- O-C (=O)-CH3)-CH2-))
3. the resin combination of item 1 or 2 as described above, wherein, the mol ratio of (a1) composition and (a2) composition in (1) composition
[(a1)/(a2)] is 1~1.5.
4. the resin combination any one of item 1~3 as described above, wherein, further containing (A1) composition beyond
Polyimides (A2).
5. the resin combination of item 4 as described above, it is characterised in that (A2) composition is makes comprising (a1) composition and/or free
Aromatic tetracarboxylic acid's dianhydride (a1 ') and (a2) composition and/or non-hydrogenated dimerization two that the content of carboxylic acid is more than 1 weight %
Polyimide resin formed by monomer group (2) reaction of amine (a2 ').
6. the resin combination of item 5 as described above, wherein, (2) composition further contains (a3) composition.
7. the resin combination any one of item 4~6 as described above, wherein, the solid of (A1) composition and (A2) composition
Weight ratio of constituents [(A1)/(A2)] is 40/60~99/1.
8. the resin combination any one of item 1~7 as described above, wherein, further containing crosslinking agent (B).
9. the resin combination of item 8 as described above, wherein, (B) composition is polyepoxy compound (B1) and/or polyphenylene oxide chemical combination
Thing (B2).
10. the resin combination of item 9 as described above, wherein, (B1) composition is the four glycidyl group benzene diformazan of following structures
Base diamines.
(in formula, Z1Represent phenylene or cyclohexylidene)
11. the polyimide resin composition of item 9 or 10 as described above, wherein, (B2) composition is the hydroxyl of following structures
Polyphenylene oxide.
(in formula, Z2The alkylidene or singly-bound of carbon number 1~3 are represented, m represents that 0~20, n represents 0~20, m and n conjunction
Meter expression 1~30)
12. the polyimide resin composition any one of item 1~11 as described above, wherein, further containing organic
Solvent (C).
13. the resin combination any one of item 1~12 as described above, wherein, further contain formula：Q-Si(R1)a
(OR2)3-a(in formula, Q represents the group containing the functional group reacted with anhydride group, R1The alkyl of hydrogen or carbon number 1~8 is represented,
R2Represent carbon number 1~8 alkyl, a represent 0,1 or 2) shown in reactive polyglycidyl compounds (D).
14. a kind of adhesive, it includes the resin combination any one of above-mentioned item 1~13.
15. a kind of membranaceous adhesive material, it is made up of the solidfied material of the adhesive of above-mentioned item 14.
16. a kind of sheet adhesive, it is used as adhesive layer using the solidfied material of the adhesive of above-mentioned item 14.
17. a kind of multiwiring board, it uses the adhesive being selected from by above-mentioned item 14, the membranaceous adhesive material of above-mentioned item 15
At least one of group constituted with the sheet adhesive of above-mentioned item 16 and obtain.
18. a kind of copper foil of resin, it uses the adhesive being selected from by above-mentioned item 14, the membranaceous gluing material of above-mentioned item 15
Expect at least one of group constituted with the sheet adhesive of above-mentioned item 16 and obtain.
19. a kind of copper foil of resin, it is obtained using the copper foil of the resin of above-mentioned item 18.
20. a kind of printed wiring board, it is obtained using the copper-clad laminated board of above-mentioned item 19.
Invention effect
Initial stage adhesivity of the resin combination of the present invention not only to various base materials is good, and adhesive tension is good.In addition,
Its solidfied material (gluing oxidant layer) it is sticky low, do not produce foaming in heating, be not likely to produce generation of adhesive deposit, and adhesive tension and low
Dielectric property is excellent.
The resin combination and solidfied material are used as tellite (increasing layer substrate, flexible printed board etc.) and flexible print
Brush substrate is with the carrier band of the adhesive, TAB bands and COF of the manufacture of copper-clad plate band etc. and adhesive, the semiconductor layer of slide glass
Between the electrically insulating material such as material, coating agent, resist ink etc. it is useful.
In addition, multiwiring board, the copper foil of resin, copper-clad laminated board and the printed wiring board of the present invention are respectively provided with this hair
The solidfied material (adhesive layer) of bright adhesive, this make it that adhesive tension and low dielectric property are excellent, therefore, as requiring the low of height
The product of dielectric property, for example using smart mobile phone, mobile phone as representative portable communication apparatus or its base station apparatus, servo
The material of the product of the processing high-frequency signal such as the network such as device/router associated electronic device, mainframe computer is useful.
Embodiment
The resin combination of the present invention includes the aromatic tetracarboxylic acid two for making the content containing free carboxy acid be less than 1 weight %
Acid anhydride (a1) (hereinafter also referred to as (a1) composition) and hydrogenation dimer diamine (a2) (hereinafter also referred to as (a2) composition) and without diamino
The monomer group (1) (hereinafter also referred to as (1) composition) of based polysiloxane (a3) (hereinafter also referred to as (a3) composition) is reacted and formed
Polyimides (A1) (hereinafter also referred to as (A1) composition).
As (a1) composition, it is less than 1 weight using various known aromatic tetracarboxylic acid's dianhydrides, the i.e. content of free carboxy acid
Measure %, preferably below 0.5 weight %, most preferably below 0.2 weight % composition., can by using (a1) composition
Maintain the adhesive tension of the adhesive of the present invention and improve its low dielectric property.
As above-mentioned aromatic tetracarboxylic acid's dianhydride, such as pyromellitic acid dianhydride, 4, the double phthalic acids of 4 '-oxygen can be enumerated
Dianhydride, 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 3,3 ', 4,4 '-diphenyl ether tetracarboxylic dianhydride, 3,3 ', 4,4 '-hexichol
Base sulfone tetracarboxylic dianhydride, 1,2,3,4- benzene tertacarbonic acids dianhydride, 1,4,5,8- naphthalene tetracarboxylic acids dianhydride, 2,3,6,7- naphthalene tetracarboxylic acids two
Acid anhydride, 3,3 ', 4,4 '-biphenyl tetracarboxylic dianhydride, 2,2 ', 3,3 '-biphenyl tetracarboxylic dianhydride, 2,3,3 ', 4 '-biphenyltetracarboxyacid acid two
Acid anhydride, 2,3,3 ', 4 '-benzophenone tetracarboxylic dianhydride, 2,3,3 ', 4 '-diphenyl ether tetracarboxylic dianhydride, 2,3,3 ', 4 '-diphenyl
Sulfone tetracarboxylic dianhydride, double (3,3 ', 4,4 '-tetracarboxylic phenyl) the tetrafluoropropane dianhydrides of 2,2-, 2,2 '-bis- (3,4- dicarboxyl benzene oxygen
Base phenyl) sulfone dianhydride, double (2,3- dicarboxyphenyis) propane dianhydrides of 2,2-, double (3,4- dicarboxyphenyis) propane dianhydrides of 2,2-,
4,4 '-[propane -2,2- diyl is double (Isosorbide-5-Nitrae-phenylene epoxide)] double O-phthalic acid dianhydrides etc., can be by two or more carry out groups
Close.
(in formula, X represents singly-bound ,-SO2-、-CO-、-O-、-O-C6H4-C(CH3)2-C6H4- O- or-COO-Y-OCO- (Y tables
Show-(CH2)l- (l=1~20) or-H2C-HC (- O-C (=O)-CH3)-CH2-))
As above-mentioned aromatic tetracarboxylic acid's dianhydride, examined from the adhesive tension of adhesive and the viewpoint of low dielectric property of the present invention
Consider, be preferably selected from by 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride, 4, the 4 '-[double (Isosorbide-5-Nitraes-phenylene oxygen of propane -2,2- diyl
At least one of base)] groups of the double O-phthalic acid dianhydrides compositions of double O-phthalic acid dianhydrides and 4,4 '-oxygen.
As above-mentioned free carboxy acid, such as aromatic tetracarboxylic acid, the acid anhydride of aromatic tetracarboxylic acid one, aromatic series tricarboxylic can be enumerated
Acid, aromatic tricarboxylic acids acid anhydride, aromatic dicarboxylic acid, aromatic dicarboxylic acid acid anhydride etc..For example, in above-mentioned 3,3 ', 4,4 '-benzophenone
In the case of tetracarboxylic dianhydride, 3,3 ', 4 can be enumerated, 4 '-benzophenone tetrabasic carboxylic acid or one acid anhydride and 3,3 ', 4- benzophenone
Tricarboxylic acids (refers to following structures, about 356) etc. molecular weight is.
The content of above-mentioned free carboxy acid in above-mentioned (a1) composition can be using various known analysis means, for example efficient
Liquid chromatogram (HPLC), quality analysis apparatus (GC-MASS) etc. are quantified.
Above-mentioned (a2) composition be as derived from the dimeric dibasic acid of the dimer as unrighted acids such as oleic acid polymer (day
This Unexamined Patent 9-12712 publications etc. refer to) hydride, below, the non-limiting structural formula of dimeric dibasic acid is shown.Each structure
In formula, m+n=6~17, p+=8~19, dotted line part represents carbon-to-carbon singly-bound or carbon-to-carbon double bond.(a2) composition is that the carbon-to-carbon is double
Structure after at least one or all formation singly-bound of key.
As the commercially available product of (a2) composition, such as PRIAMINE1075 (manufacture of He great Amada Co., Ltd.s) can be enumerated
Deng.Hereinafter, one of hydrogenation dimer diamine is shown.
The mol ratio [(a1)/(a2)] of above-mentioned (a1) composition and (a2) composition in above-mentioned (1) composition is not particularly limited,
From the viewpoint of the balance of adhesive tension and low dielectric property, typically about 1~about 1.5, preferably from about 1~about 1.2.
It should be noted that in the present invention, from the viewpoint of low dielectric property, not contained in above-mentioned (1) composition above-mentioned
(a3) composition.The concrete example for being somebody's turn to do (a3) composition is as described later.
The diamines beyond above-mentioned (a1) composition~(a3) composition can be contained in above-mentioned (1) composition (hereinafter also referred to as (a4)
Composition).Specifically, it can enumerate for example：Diaminocyclohexane, diamino-dicyclohexyl methane, the ring of dimethyl diaminourea two
It is hexyl methane, tetramethyl diamino-dicyclohexyl methane, diaminocyclohexyl propane, the ring of diaminourea two [2.2.1] heptane, double
(amino methyl) two ring [2.2.1] heptane, 3 (4), 8 (9)-bis- (amino methyl) three ring [5.2.1.02,6] decane, the double ammonia of 1,3-
The ester ring type diamines such as ylmethyl hexamethylene, IPD；Double [4- (3- amino-benzene oxygens) phenyl] propane of 2,2-, 2,2- are double
Double aminophenoxy phenyl propane classes such as [4- (4- amino-benzene oxygens) phenyl] propane；3,3 '-diamino-diphenyl ether, 3,4 '-
The diamino-diphenyl ethers such as diamino-diphenyl ether, 4,4 '-diamino-diphenyl ether；The benzene such as p-phenylenediamine, m-phenylene diamine (MPD) two
Amine；The diaminos such as 3,3 '-diamino diphenyl sulfide, 3,4 '-diamino diphenyl sulfide, 4,4 '-diamino diphenyl sulfide
Base diphenylsulfide class；3,3 '-diamino diphenyl sulfone, 3,4 '-diamino diphenyl sulfone, 4,4 '-diamino diphenyl sulfone etc.
Diamino diphenyl sulfone class；3,3 '-diaminobenzophenone, 4,4 '-diaminobenzophenone, 3,4 '-diaminobenzophenone
Deng diaminobenzophenone class；3,3 '-diaminodiphenyl-methane, 4,4 '-diaminodiphenyl-methane, 3,4 '-diaminourea two
The diaminodiphenyl-methane class such as phenylmethane；2,2- bis- (3- aminophenyls) propane, 2,2- bis- (4- aminophenyls) propane, 2-
The diamino-phenyl propane classes such as (3- aminophenyls) -2- (4- aminophenyls) propane；2,2- bis- (3- aminophenyls) -1,1,1,3,
3,3- HFC-236fas, 2,2- bis- (4- aminophenyls) -1,1,1,3,3,3- HFC-236fas, 2- (3- aminophenyls) -2- (4- amino
Phenyl) the diamino-phenyl HFC-236fa class such as -1,1,1,3,3,3- HFC-236fas；1,1- bis- (3- aminophenyls) -1- phenyl second
Alkane, 1,1- bis- (4- aminophenyls) -1- diphenylphosphino ethanes, 1- (3- aminophenyls) -1- (4- aminophenyls) -1- diphenylphosphino ethanes etc. two
Aminophenylphenyl ethane；Double (3- amino-benzene oxygens) benzene of 1,3-, double (4- amino-benzene oxygens) benzene of 1,3-, double (the 3- ammonia of 1,4-
Phenoxyl) double amino-benzene oxygen benzene classes such as benzene, double (4- amino-benzene oxygens) benzene of 1,4-；1,3- is double (3- amino benzoyls)
Double (4- amino benzoyls) benzene of benzene, 1,3-, double (3- amino benzoyls) benzene of 1,4-, double (4- amino benzoyls) benzene of 1,4-
Deng double amino benzoyl benzene classes；Double (3- amino-bis (alpha, alpha-dimethylbenzyl) base) benzene of 1,3-, double (the 4- amino-alpha, alpha-dimethyl of 1,3-
Benzyl) double ammonia such as benzene, double (3- amino-bis (alpha, alpha-dimethylbenzyl) base) benzene of 1,4-, double (4- amino-bis (alpha, alpha-dimethylbenzyl) base) benzene of 1,4-
Base dimethyl benzene class；Double (3- amino-α, the α-bistrifluoromethylbenzyl) benzene of 1,3-, 1,3- double (4- amino-α, α-bis trifluoromethyl
Benzyl) benzene, double (3- amino-α, the α-bistrifluoromethylbenzyl) benzene of 1,4-, 1,4- are double (4- amino-α, α-bistrifluoromethylbenzyl)
Double amino bistrifluoromethylbenzyl benzene classes such as benzene；Double (3- amino-benzene oxygens) benzonitriles of 2,6-, 2,6- are double (3- amino-benzene oxygens)
The amino-benzene oxygen biphenyl classes such as pyridine, 4,4 '-bis- (3- amino-benzene oxygens) biphenyl, 4,4 '-bis- (4- amino-benzene oxygens) biphenyl；It is double
The aminophenoxy phenyl ketones such as [4- (3- amino-benzene oxygens) phenyl] ketone, double [4- (4- amino-benzene oxygens) phenyl] ketone；Double [4-
(3- amino-benzene oxygens) phenyl] the aminophenoxy phenyl thioether class such as thioether, double [4- (4- amino-benzene oxygens) phenyl] thioethers；It is double
The aminophenoxy phenyl sulfone classes such as [4- (3- amino-benzene oxygens) phenyl] sulfone, double [4- (4- amino-benzene oxygens) phenyl] sulfones；Double [4-
(3- amino-benzene oxygens) phenyl] the aminophenoxy phenyl ethers such as ether, double [4- (4- amino-benzene oxygens) phenyl] ethers；2,2- is double
Double [3- (3- amino-benzene oxygens) the phenyl] -1,1,1,3,3,3- HFC-236fas of [4- (3- amino-benzene oxygens) phenyl] propane, 2,2-,
The aminophenoxy phenyl propane classes such as double [4- (4- amino-benzene oxygens) the phenyl] -1,1,1,3,3,3- HFC-236fas of 2,2-；And
Double [4- (3- amino-benzene oxygens) benzoyl] benzene of 1,3-, double [4- (4- amino-benzene oxygens) benzoyl] benzene of 1,3-, 1,4- are double
Double [4- (4- amino-benzene oxygens) benzoyl] benzene of [4- (3- amino-benzene oxygens) benzoyl] benzene, 1,4-, the double [4- (3- of 1,3-
Amino-benzene oxygen)-bis (alpha, alpha-dimethylbenzyl) base] benzene, 1,3- double [4- (4- amino-benzene oxygens)-bis (alpha, alpha-dimethylbenzyl) base] benzene, 1,4-
Double [4- (3- amino-benzene oxygens)-bis (alpha, alpha-dimethylbenzyl) base] benzene, 1,4- are double [4- (4- amino-benzene oxygens)-bis (alpha, alpha-dimethylbenzyl) base]
Benzene, 4,4 '-bis- [4- (4- amino-benzene oxygens) benzoyl] diphenyl ethers, 4,4 '-bis- [4- (4- amino-bis (alpha, alpha-dimethylbenzyl)
Base) phenoxy group] benzophenone, 4,4 '-bis- [4- (4- amino-bis (alpha, alpha-dimethylbenzyl) base) phenoxy group] diphenyl sulfones, 4,4 '-it is bis-
[4- (4- amino-benzene oxygens) phenoxy group] diphenyl sulfone, '-two of 3,3 '-diaminourea -4,4 phenoxy benzophenone, 3,3 '-diamino
Base -4,4 '-bigeminy phenoxy benzophenone, 3,3 '-diaminourea -4- phenoxy benzophenones, 3,3 '-diaminourea -4- biphenyl oxygen
Base benzophenone, 6,6 '-bis- (3- amino-benzene oxygens) 3,3,3, ' 3, '-tetramethyl -1,1 '-spiro indan, 6,6 '-bis- (4- ammonia
Phenoxyl) 3,3,3, ' 3, '-tetramethyl -1,1 '-spiro indan, 1,3- double (3- aminopropyls) tetramethyl disiloxane, 1,
3- double (4- aminobutyls) tetramethyl disiloxane, double (amino methyl) ethers, double (2- amino-ethyls) ethers, double (3- aminopropyls)
Ether, double [(2- aminomethoxies) ethyl] ethers, double [2- (2- amino ethoxies) ethyl] ethers, double [2- (3- amino propoxyl group) second
Base] ether, double (aminomethoxy) ethane of 1,2-, double (2- amino ethoxies) ethane of 1,2-, double [2- (aminomethoxy) second of 1,2-
Epoxide] ethane, double [2- (2- amino ethoxies) ethyoxyl] ethane of 1,2-, ethylene glycol double (3- aminopropyls) ether, diethylene glycols
Double (3- aminopropyls) ethers, triethylene glycol double (3- aminopropyls) ether, ethylenediamine, 1,3- diaminopropanes, 1,4- diaminourea fourths
Alkane, 1,5- 1,5-DAPs, 1,6- diamino hexanes, 1,7- diaminoheptanes, 1,8- diamino-octanes, 1,9- diaminourea nonyls
Alkane, 1,10- diamino decanes, 1,11- diamino undecanes, 1,12- diamino dodecanes etc., can be by two or more carry out groups
Close.Wherein, from the viewpoint of low dielectric property, preferably above-mentioned ester ring type diamines.(a4) usage amount of composition is not limited especially
It is fixed, in the case where whole diamine components are set into 100 moles of %, usually less than 40 moles %.
(A1) composition can be manufactured by various known methods.Specifically, for example, can be by the acid used respectively
Composition and diamine component carried out at a temperature of typically about 60 DEG C~about 120 DEG C typically about 0.1 hour~about 2 hours plus
Poly- reaction.Then, by resulting addition polymers further about 80 DEG C~about 250 DEG C, be preferably 100~200 DEG C at a temperature of
Imidization reaction, the i.e. dehydration closed-loop reaction of progress about 0.5 hour~about 50 hours.In addition, when these react, can
To use (C) composition described later, particularly aprotic polar solvent to be used as reaction dissolvent.
In imidization reaction, various known catalysts, dehydrating agent and solvents described later can be used.As anti-
Answer catalyst, can enumerate the aromatic tertiary amines such as the aliphatic tertiary amine such as triethylamine class, dimethylaniline, pyridine, picoline,
Hetero ring type tertiary amines such as isoquinolin etc., can be combined two or more.In addition, as dehydrating agent, such as second can be enumerated
Aromatic anhydride such as the aliphatic anhydrides such as acid anhydrides or benzoyl oxide etc., can be combined two or more.
Imide ring closure rate is not particularly limited, usually more than 70%, preferably 85~100%.Here, " acid imide
Closed loop rate " refers to the content (following same) of the cyclic imide key in (A1) composition, such as can be analyzed by NMR, IR
Various light splitting means are determined.
(A1) physical property of composition is not particularly limited, from the viewpoint of the balance of adhesive tension and low dielectric property, generally,
Number-average molecular weight (referring to the polystyrene scaled value obtained by gel permeation chromatography, below equally) is about 5000~about
50000th, 7000~about 30000 are preferably from about, glass transition temperature (JIS-K7121) is about 30 DEG C~about 160 DEG C, is preferably
About 40 DEG C~about 140 DEG C.In addition, the concentration of the end anhydride group of (A1) composition is also not particularly limited, typically about 2000eq/
G~about 40000eq/g, preferably from about 3000eq/g~about 20000eq/g.
It should be noted that (A1) composition further can be entered its molecular end using the primary alkyl monoamine of low molecule amount
Row is modified (sealing).As its concrete example, such as ethamine, n-propylamine, isopropylamine, n-butylamine, isobutyl amine, Zhong Ding can be enumerated
Amine, tert-butylamine, amylamine, iso-amylamine, tertiary amylamine, n-octyl amine, n-Decylamine, isodecyl amine, positive tridecyl amine, positive lauryl amine, positive cetylamine
With positive stearylamine etc., particularly from the viewpoint of low dielectric property, preferably the carbon number of alkyl is 4~15 or so primary alkane
Base monoamine.In addition, the usage amount of the primary alkyl monoamine is also not particularly limited, the end anhydride group 1 relative to (A1) composition is rubbed
You, typically about 0.8 mole~about 1.2 moles, preferably from about 0.9 mole~about 1.1 moles.
In the resin combination of the present invention, the polyimides (A2) beyond above-mentioned (A1) composition can be contained and (below, be also referred to as
For (A2) composition).
(A2) as long as the polyimides beyond above-mentioned (A1) composition of composition can then use various known materials, preferably
The aromatic tetracarboxylic acid's dianhydride for making the content comprising above-mentioned (a1) composition and/or free carboxy acid be more than 1 weight % can be enumerated
(a1 ') (hereinafter also referred to as (a1 ') composition) and above-mentioned (a2) composition and/or non-hydrogenated dimer diamine (a2 ') (it is following, also referred to as
For (a2 ') composition) monomer group (2) (hereinafter also referred to as (2) composition) reaction formed by polyimides (wherein, exclude suitable
In the polyimides of above-mentioned (A1) composition).
As (a1 ') composition, as long as the content of above-mentioned free carboxy acid is 1 weight % in above-mentioned aromatic tetracarboxylic acid's dianhydride
Composition above, then can be without particular limitation using various known materials.Alternatively, it is also possible to will be in above-mentioned (a1) composition
In used using the material for making its content combine above-mentioned free carboxy acid in the way of more than 1 weight % as (a1 ') composition.From dimension
From the viewpoint of holding the adhesive tension of the adhesive of the present invention and improving its low dielectric property, this that should be in (a1 ') composition dissociates
The higher limit of the content of carboxylic acid is usually below 5 weight %.
As (a2 ') composition, the composition such as described in above-mentioned Japanese Unexamined Patent Publication 9-12712 publications can be enumerated,
As commercially available product, such as バ-サ ミ Application 551 (manufacture of BASF Amada Co., Ltd.s), PRIAMINE1074 (standing grain big days can be illustrated
This Co., Ltd. manufactures).
(2) in composition, (a3) composition can also be contained.As (a3) composition, various known diaminourea can be enumerated and gathered
Siloxanes, for example, α can be illustrated, ω-bis- (2- amino-ethyls) dimethyl silicone polymer, α, ω-bis- (3- aminopropyls) poly- two
Methylsiloxane, α, ω-bis- (4- aminobutyls) dimethyl silicone polymer, α, ω-bis- (5- Aminopentyls) polydimethylsiloxanes
Alkane, α, ω-bis- [3- (2- aminophenyls) propyl group] dimethyl silicone polymer, α, ω-bis- [3- (4- aminophenyls) propyl group] poly- two
Methylsiloxane etc..
Hereinafter, the typical example of the combination of raw material in (2) composition is shown.
I. (a1) composition, (a2) composition and (a3) composition
Ii. (a1) composition and (a2 ') composition
Iii. (a1) composition, (a2 ') composition and (a3) composition
Iv. (a1 ') composition and (a2) composition
V. (a1 ') composition, (a2) composition and (a3) composition
Vi. (a1 ') composition and (a2 ') composition
Vii. (a1 ') composition, (a2 ') composition and (a3) composition
Viii. (a1) composition, (a2) composition and (a4) composition
Iv. (a1 ') composition, (a2) composition and (a4) composition
X. (a1) composition, (a2 ') composition and (a4) composition
(2) mol ratio of (a1) composition and/or (a1 ') composition in composition and (a2) composition and/or (a2 ') composition
[(a1, a1 ')/(a2, a2 ')] it is not particularly limited, typically about 1~about 1.5, preferably from about 1~about 1.2.
In addition, in the case of containing (a3) composition in (2) composition, its usage amount is also not particularly limited, generally, inciting somebody to action
It is about 0.1 mole of %~about 5.0 mole % in the case that whole diamine components are set to 100 moles of %.
It should be noted that in (2) composition, (a4) composition can also be contained.In this case, the usage amount of (a4) composition
It is not particularly limited, in the case where whole diamine components are set into 100 moles of %, usually less than 40 moles %.
(A2) manufacture method of the manufacture method of composition according to (A1) composition.(A2) the imide ring closure rate of composition does not have yet
It is particularly limited to, usually more than 70%, preferably 85~100%.
(A2) physical property of composition is not particularly limited, from the viewpoint of the balance of adhesive tension and low dielectric property, generally,
Number-average molecular weight (referring to the polystyrene scaled value obtained by gel permeation chromatography, below equally) is about 5000~about
50000th, 7000~about 30000 are preferably from about, glass transition temperature (JIS-K7121) is about 30 DEG C~about 160 DEG C, is preferably
About 40 DEG C~about 140 DEG C.In addition, the concentration of the end anhydride group of (A2) composition is also not particularly limited, typically about 2000eq/
G~about 40000eq/g, preferably from about 3000eq/g~about 20000eq/g.
It should be noted that (A2) composition its molecular end can be modified using above-mentioned primary alkyl monoamine it is (close
Envelope).
(A1) the solids by weight ratio [(A1)/(A2)] of composition and (A2) composition is not particularly limited, containing both
From the viewpoint of the dielectric property of the solidfied material of composition is especially low, usually 30/70~90/10 or so, preferably 40/60~
99/1 or so.
In the resin combination of the present invention, it can further contain crosslinking agent (B) (hereinafter also referred to as (B) composition).
As (B) composition, such as multi-epoxy can be enumerated without particular limitation using various known crosslinking agents
Compound (B1) (hereinafter also referred to as (B1) composition), polyphenylene ether compound (B2) (hereinafter also referred to as (B2) composition) and except this
Crosslinking agent in addition (hereinafter also referred to as (B3) composition).Wherein, preferably (B1) composition and/or (B2) composition.
As (B1) composition, such as phenol novolak-type epoxy compound, cresol novolak type epoxy can be enumerated
Compound, bisphenol A type epoxy compound, bisphenol F type epoxy compound, bisphenol S type epoxy compound, hydrogenated bisphenol A type epoxy
Compound, A Hydrogenated Bisphenol A F types epoxide, stilbene type epoxide, the epoxide of the skeleton containing triazine, containing fluorene skeleton
Epoxide, linear aliphatic race epoxide, cycloaliphatic epoxy, glycidyl amine epoxy compound, triphenol
Methylmethane type epoxide, alkyl-modified triphenol methylmethane type epoxide, biphenyl type epoxy compound, containing bicyclic penta 2
The epoxide of alkene skeleton, the epoxide containing naphthalene skeleton, aryl alkene fundamental mode epoxide, four glycidyl group benzene
Dimethyl-p-phenylenediamine, these epoxides using dimer acid modified modified epoxy compound, dimeric dibasic acid two are shunk sweet
Oil base ester etc., can be combined two or more.In addition, as commercially available product, such as Mitsubishi chemical Co., Ltd can be enumerated
" jER828 ", " jER834 ", " jER807 ", " jER630 ", " ST-3000 " of Nippon Steel Chemical Co., Ltd's manufacture of manufacture,
" セ ロ キ サ イ De 2021P ", " YD- of Nippon Steel Chemical Co., Ltd's manufacture of Daisel chemical industry Co., Ltd's manufacture
172-X75 " etc..
(B1) in composition, from the viewpoint of intermiscibility, heat resistance, the four glycidyl group benzene two of more preferably following structures
Methanediamine, can use the commercially available product such as " Tetrad-X " that Mitsubishi Gas Chemical Co., Ltd manufactures.
(in formula, Z1Represent phenylene or cyclohexylidene)
It should be noted that in the case where using (B1) composition, various known epoxides can be applied in combination
Use curing agent.Specifically, such as succinic anhydride, phthalic anhydride, maleic anhydride, trimellitic anhydride, equal benzene can be enumerated
Four acid anhydrides, hexahydrophthalic anhydride, 3- methylhexahydrophthalic anhydrides, 4- methylhexahydrophthalic anhydrides or 4-
The adjacent benzene of mixture, tetrabydrophthalic anhydride, methyl tetrahydrochysene of methylhexahydrophthalic anhydride and hexahydrophthalic anhydride
Dicarboxylic acid anhydride, carbic anhydride, methylnadic anhydride, norbornane -2,3- dicarboxylic anhydrides, methyl norbornane -2,3- two
The acid anhydride type curing agents such as carboxylic acid anhydrides, methylcyclohexene dicarboxylic anhydride, 3- dodecenyl succinic anhydrides, octenyl succinic acid anhydride；
(trade name " LonzacureM-DEA ", " LonzacureM-DETDA " etc. are imperial husky for dicyandiamide (DICY), aromatic diamine
Amada Co., Ltd. manufactures), the amine curing agent such as aliphatic amine；Phenol resol resins, cresol novolac resin, bis-phenol
A types novolac resin, triazine modified phenol novolac resin, the phosphonitrile (Otsuka Chemical Co., Ltd manufacture of phenolic hydroxy group
Trade name " SPH-100 " etc.) etc. phenols curing agent, cyclic phosphazene class compound, maleic acid modified rosin or its hydride etc.
Rosin crosslinking agent etc., can be combined two or more.Wherein, preferably phenols curing agent, particularly phenolic hydroxy group phosphorus
Nitrile curing agent.The usage amount of these curing agent is not particularly limited, and the solid constituent of the adhesive of the present invention is being set into 100
In the case of weight %, the weight % of typically about 0.1 weight %~about 120 weight %, preferably from about 10 weight %~about 40.
In addition, in the case where using (B1) composition, curing catalysts can also be used.Specifically, example can be enumerated
Such as：The ring of 1,8- diazas-two [5.4.0] endecatylene -7, triethylenediamine, benzyldimethylamine, 2,4, triethanolamine, dimethylamino
The tertiary amines such as ethanol, three (dimethylaminomethyl) phenol；2-methylimidazole, 2- phenylimidazoles, 2- phenyl -4-methylimidazole,
The imidazoles such as 2-ethyl-4-methylimidazole, 1- cyano ethyl -2- undecyl imidazoles, 2- heptadecyl imidazoles；Tributylphosphine,
Organic phosphines such as methyldiphenyl base phosphine, triphenylphosphine, diphenylphosphine, Phenylphosphine；TetraphenylTetraphenyl borate salts, 2- ethyls-
The tetraphenyl boron salts such as 4-methylimidazole tetraphenyl borate salts, N-methylmorpholine tetraphenyl borate salts；Octanesulfonic acid, stearic acid, acetyl
The organic metal salts such as Zn, Cu and Fe of the organic acids such as acetone solvate, aphthenic acids and salicylic acid, can be by two or more carry out groups
Close.In addition, the usage amount of the catalyst is not particularly limited, the solid constituent of the adhesive of the present invention is being set to 100 weights
In the case of measuring %, the weight % of typically about 0.01 weight %~about 5.
, can be without particular limitation using various known polyphenylene ether compounds as (B2) composition.Specifically, it is excellent
Select the polyphenylene ether compound shown in following formulas.
(in formula, Z2The alkylidene or singly-bound of carbon number 1~3 are represented, m represents that 0~20, n represents 0~20, m and n conjunction
Meter expression 1~30)
(B2) physical property of composition is not particularly limited, from the viewpoint of adhesive tension and low dielectric property, generally, it is preferred to last
Terminal hydroxy group concentration is about 900 μm of ol/g~about 2500 μm ol/g and number-average molecular weight is about 800~about 2000.
As (B3) composition, it can enumerate and be selected from by benzoPiperazine compound, bismaleimide compound and cyanogen
At least one of group of ester compound composition.
It is used as above-mentioned benzoPiperazine compound, can enumerate double (3, the 4- dihydro -3- benzene of such as 6,6- (1- methyl ethidine)
Base -2H-1,3- benzosPiperazine), the double (3,4- dihydro -3- methyl -2H-1,3- benzos of 6,6- (1- methyl ethidine)Piperazine) etc.,
It can be combined two or more.It should be noted thatPhenyl, methyl, cyclohexyl etc. can be bonded with the nitrogen of piperazine ring.
In addition, as commercially available product, " the benzo of such as Shikoku Chem's manufacture can be enumeratedPiperazine F-a types ", " benzo
" RLV-100 " of piperazine P-d types ", エ ア ウ ォ-タ-company's manufacture etc..
As above-mentioned bismaleimide compound, such as 4 can be enumerated, 4 '-diphenyl methane BMI,
Phenylene BMI, bisphenol-A diphenyl ether BMI, 3,3 '-dimethyl -5,5 '-'-two of diethyl -4,4
Phenylmethane BMI, 4- methyl isophthalic acids, 3- phenylenes BMI, 1,6 '-BMI-(2,2,4-
Trimethyl) hexane, 4,4 '-diphenyl ether BMI, 4,4 '-diphenyl sulfone BMI etc. can be by two kinds
It is combined above.In addition, as commercially available product, can enumerate such as " BAF-BMI " that JFE KCCs manufacture.
As above-mentioned cyanate esters, such as 2- chavicols cyanate, 4- metoxyphenol cyanic acid can be enumerated
Double (4- cyanato-s the phenol) -1,1,1,3,3,3- HFC-236fas of ester, 2,2-, bisphenol A cyanate, diallyl bisphenol cyanate,
Double (the 4- cyanato-s of 4- phenylphenols cyanate, 1,1,1- tri- (4- cyanato-s phenyl) ethane, 4- cumyl phenols cyanate, 1,1-
Phenyl) ethane, 4, double (4- cyanato-s phenyl) propane of 4 '-bis-phenol cyanate and 2,2- etc. can be combined two or more.
In addition, as commercially available product, can enumerate such as " PRIMASET BTP-6020S (manufacture of Long Sha Amada Co., Ltd.s) ",
" CYTESTER TA (Mitsubishi Gas Chemical Co., Ltd's manufacture) " etc..
(B) usage amount of composition is not particularly limited, and (below, incite somebody to action both sometimes relative to (A1) composition and (A2) composition
Be referred to as (A) composition) total 100 parts by weight, the parts by weight of typically about 3 parts by weight~about 30, preferably from about 5 parts by weight~about
25 parts by weight.
In the resin combination of the present invention, organic solvent (C) can be contained (hereinafter also referred to as (C) composition).
, can be without particular limitation using various known solvents as (C) composition.As concrete example, it can enumerate
Such as METHYLPYRROLIDONE, dimethylformamide, dimethyl acetamide, dimethyl sulfoxide (DMSO), N- methyl caprolactams, three
The aprotic polar solvents such as glycol dimethyl ether (methyltriglyme), diethylene glycol dimethyl ether (methyldiglyme),
The aromatic series such as alcohols solvent, the toluene such as the ester ring type such as cyclohexanone, hexahydrotoluene solvent, methanol, ethanol, propyl alcohol, benzylalcohol, cresols
Class solvent etc., can be combined two or more.Wherein, particularly from the viewpoint of low dielectric property, optimization aromatic
Class solvent.
(C) usage amount of composition is not particularly limited, generally, relative to the parts by weight of (A) composition 100, is about 0.1 parts by weight
~about 10 parts by weight, the parts by weight of preferably from about 1 parts by weight~about 5.
In the resin combination of the present invention, it can further contain formula：Q-Si(R1)a(OR2)3-a(in formula, Q represents to contain
There are the group for the functional group reacted with anhydride group, R1Represent the alkyl of hydrogen or carbon number 1~8, R2Represent carbon number 1~8
Alkyl, a represent 0,1 or 2) shown in reactive polyglycidyl compounds (D) (hereinafter also referred to as (D) composition).As
The reactive functional groups contained in Q, can enumerate amino, epoxy radicals and mercapto etc..
(D) composition is utilized, the low dielectric property of the cured layer of the adhesive of the present invention is able to maintain that and adjusts its melting
Viscosity.As a result, it is possible to improve the interface closing force (so-called anchoring effect) of the cured layer and base material, and it can suppress from the base
The oozing out of the cured layer (following, the operation is referred to as flow control sometimes) that material end is produced.
As the compound that the functional group in Q is amino, such as N-2- (amino-ethyl) -3- aminopropyl first can be enumerated
Base dimethoxysilane, N-2- (amino-ethyl) -3- TSL 8330s, 3- TSL 8330s,
APTES and 3- acyl ureidopropyltrialkoxysilanes etc..
As the compound that the functional group in Q is epoxy radicals, such as 2- (3,4- epoxycyclohexyl) ethyl three can be enumerated
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 mercapto, such as 3-mercaptopropyi trimethoxy silane, 3- can be enumerated
Mercaptopropyltriethoxysilane, 3- mercaptopropyis methyl dimethoxysilane and 3- mercaptopropyi methyldiethoxysilanes
Deng.
As (D) composition, from working well that the end anhydride group fast reaction with (A) composition and above-mentioned flow are controlled
From the viewpoint of, the functional group in preferably Q is the compound of amino.
(D) usage amount of composition is not particularly limited, generally, relative to the parts by weight of (A) composition 100, is about 0.01 weight
Part~about 5 parts by weight, the parts by weight of preferably from about 0.1 parts by weight~about 3.
The adhesive of the present invention includes resin combination, can directly use the resin combination, can also be according to need
Coordinate above-mentioned esterification by ring opening catalysts, it is dehydrating agent, plasticizer, weather resisting agent, antioxidant, heat stabilizer, lubricant, anti-
Electrostatic agent, brightening agent, colouring agent, conductive agent, releasing agent, surface conditioning agent, viscosity modifier, phosphorus flame retardant, fire-retardant filler,
Additive or the retarder thinners such as silicon filler, fluorine filler.
The membranaceous adhesive material of the present invention is that the adhesive for making the present invention is solidified and obtained using various known means
The material arrived.Specifically, it can enumerate for example by the way that the adhesive is applied on various supporters and heated, make
(C) composition volatilization and solidify after, from the supporter peel off obtained from material, the material can be used as membranaceous adhesive material profit
With.In addition, coating means are not particularly limited, curtain can be enumerated and apply machine, roll coater, laminating machine etc..In addition, the thickness of coating layer
Also it is not particularly limited, dried thickness is typically about 1 μm~about 100 μm, preferably from about 3 μm~about 50 μm of scope.
The sheet adhesive of the present invention is the article using above-mentioned solidfied material as adhesive layer.Specifically, by above-mentioned solidfied material and
Various known plate substrates are constituted, and as the plate substrate, can enumerate such as polyester, polyimides, polyimides-silica
Hybrid, polyethylene, polypropylene, polyethylene terephthalate, PEN, polymethyl methacrylate
Resin, polystyrene resin, polycarbonate resin, acrylonitrile-butadiene-styrene resin, by ethylene glycol terephthalate,
(so-called liquid crystal gathers the aromatic series kind polyester resin that phenol, phthalic acid, hydroxynaphthoic acid etc. are obtained with P-hydroxybenzoic acid
Compound；Kuraray Co., Ltd. manufacture " ベ Network ス タ ー " etc.) etc. plastic foil.The thickness of the adhesive layer is not also limited especially
It is fixed, typically about 1 μm~about 100 μm, preferably from about 3 μm~about 50 μm of scope.
The present invention multiwiring board be use be selected from by above-mentioned polyimide adhesive, above-mentioned membranaceous adhesive material and
Article obtained from least one of group of above-mentioned sheet adhesive composition.Specifically, it can obtain by the following method：Use
Above-mentioned material forms adhesive layer at least one face of the printed wiring board as core base material, and is laminated thereon other printings
Wiring plate or printed circuit board (PCB), are then crimped under heating and pressurization.Heating-up temperature, crimping time and pressure is not special
Limit, typically about 70 DEG C~about 200 DEG C, about 1 minute~about 3 hours, about 0.5MPa~about 20MPa.
The copper foil of the resin of the present invention is to use to be selected from by above-mentioned polyimide adhesive, above-mentioned membranaceous adhesive material
At least one of group constituted with above-mentioned sheet adhesive forms article formed by adhesive layer on copper foil., can as the copper foil
To enumerate such as rolled copper foil, electrolytic copper foil, it is possible to implement various surface treatments (roughening, antirusts etc.).In addition, the copper foil
Thickness be not particularly limited, typically about 1 μm~about 100 μm, preferably from about 2 μm~about 38 μm.The copper foil of the resin
Adhesive layer can be uncured adhesive layer, can also be in addition adhesive layer partially cured under heating or being fully cured.Portion
The adhesive layer of solidification is divided to be in the state for being referred to as so-called B-stage.In addition, the thickness of adhesive layer is also not particularly limited, generally
It is about 0.5 μm~about 30 μm.Alternatively, it is also possible to the further laminating copper foil on the gluing surface of the copper foil of resulting resin
The copper foil of two sides resin is made.
The copper-clad laminated board of the present invention is that the copper foil of the resin of the present invention is fitted with copper foil or insulating properties piece
Article, also referred to as CCL (Copper Clad Laminate).Specifically by the copper foil of the resin of the present invention in heating
Under be crimped onto article obtained from least one or two sides of various known insulating properties pieces.In addition, in the case of one side, can
To crimp the materials different from the copper foil of the resin of the present invention on the other surface.In addition, the tape tree in the copper-clad laminated board
The copper foil of fat and the number of insulating trip are not particularly limited.In addition, being used as the insulating properties piece, preferably prepreg.Prepreg refers to
In the reinforcing materials such as glass cloth infiltrate resin and make its be cured to B-stage obtained from flaky material (JIS C 5603), make
For the resin, usually used polyimides, phenolic resin, epoxy resin, polyester resin, liquid crystal polymer, aromatic polyamides tree
The insulative resins such as fat.In addition, the thickness of the prepreg is not particularly limited, typically about 20 μm~about 500 μm.In addition, plus
Heat, crimping condition are not particularly limited, typically about 150 DEG C~about 280 DEG C and about 0.5MPa~about 20MPa.
The printed wiring board of the present invention is the article obtained from the copper-clad surface of above-mentioned copper-clad laminated board forms circuit pattern.
As patterning means, such as subtractive process, semi-additive process can be enumerated.As semi-additive process, for example following method can be enumerated：
After being patterned on the copper-clad surface of the copper-clad laminated board of the present invention using resist film, electrolytic copper plating is carried out, is removed against corrosion
Agent, and be etched using alkali lye.In addition, the thickness of the circuit pattern layer in the printed wiring board is not particularly limited.In addition,
It can also be printed by using the printed wiring board as core base material, known to stacking identical printed wiring board thereon or other
Brush wiring plate or printed circuit board (PCB) and obtain multilager base plate.During stacking, it can not only use the polyimide of the present invention gluing
Agent, can also use other known polyimide adhesive.In addition, the stacking number in multilager base plate is not particularly limited.
In addition, through hole can be plugged when being laminated every time, plating is carried out to inside.
[embodiment]
Hereinafter, the present invention is specifically illustrated by embodiment and comparative example, but the scope of the present invention is not by these
The restriction of example.In addition, in each example, as long as no special declaration, part and % are weight basis.
Production Example 1
Commercially available aromatic series four is put into the reaction vessel for possessing mixer, water knockout drum, thermometer and nitrogen ingress pipe
Carboxylic acid dianhydride (trade name " BTDA-UP ", the manufacture of エ ボ ニ ッ Network Amada Co., Ltd.；3,3 ', 4,4 '-benzophenone tetrabasic carboxylic acid two
The content of acid anhydride be more than 99.9%) 210.0g, cyclohexanone 1008.0g, hexahydrotoluene 201.6g, solution is heated to 60 DEG C.
Then, hydrogenation dimer diamine (trade name " manufacture of PRIAMINE 1075 ", He great Amada Co., Ltd.) 341.7g is added dropwise, then,
Imidization reaction was carried out with 10 hours at 140 DEG C, it is about 35000 with weight average molecular weight thus to obtain softening point to be about 80 DEG C
Polyimide resin (A1-1) solution (nonvolatile component 30.0%).It should be noted that mole of sour composition/amine component
Than for 1.03.
Production Example 2
Commercially available aromatic tetracarboxylic acid's dianhydride (trade name is put into the reaction vessel same with Production Example 1
" BisDA2000 ", the manufacture of contract commercial firm of SABIC Japan；4,4 '-[propane -2,2- diyls are double (1,4- phenylenes epoxide)] double neighbours
The content of phthalic acid dianhydride be more than 99.5%) 60.0g, cyclohexanone 165.0g, hexahydrotoluene 27.5g, solution is heated
To 60 DEG C.Then, 59.3g PRIAMINE 1075 is added dropwise, then, imidization reaction was carried out with 10 hours at 140 DEG C,
Thus the solution that softening point is the polyimide resin (A1-2) that about 90 DEG C and weight average molecular weight are about 30000 is obtained (non-volatile
Composition 31.9%).It should be noted that the mol ratio of sour composition/amine component is 1.05.
Comparative example Production Example 1
Commercially available aromatic tetracarboxylic acid's dianhydride (trade name " BisDA- is put into the reaction vessel same with Production Example 1
The manufacture of 1000 ", SABIC Japan contract commercial firm；4,4 '-[propane -2,2- diyls are double (1,4- phenylenes epoxide)] double O-phthalics
The content of acid dianhydride is 98.0%) 65.0g, cyclohexanone 266.5g, hexahydrotoluene 44.4g, and solution is heated into 60 DEG C.Connect
, 43.7g PRIAMINE 1075 and the 5.4g double aminomethyl cyclohexanes of 1,3- are added dropwise, it is then, small with 10 at 140 DEG C
Shi Jinhang imidization reactions, it is the polyimide resin that about 100 DEG C and weight average molecular weight are about 30000 thus to obtain softening point
(A2-1) solution (nonvolatile component 29.2%).It should be noted that the mol ratio of sour composition/amine component is 1.05.
Comparative example Production Example 2
Commercially available aromatic tetracarboxylic acid's dianhydride (trade name " BTDA- is put into the reaction vessel same with Production Example 1
PF ", エ ボ ニ ッ Network Amada Co., Ltd. manufacture；98%) content of 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydride is
200.0g, cyclohexanone 960.0g, hexahydrotoluene 192.0g, 60 DEG C are heated to by solution.Then, it is added dropwise 319.2g's
PRIAMINE 1075, then, imidization reaction was carried out at 140 DEG C with 10 hours, thus obtain softening point be about 80 DEG C and
The solution (nonvolatile component 29.8%) for the polyimide resin (A2-2) that weight average molecular weight is about 25000.It should be noted that
The mol ratio of sour composition/amine component is 1.05.
Comparative example Production Example 3
BTDA-PF 190.0g, cyclohexanone 277.5g, hexahydrotoluene are put into the reaction vessel same with Production Example 1
182.4g, 60 DEG C are heated to by solution.Then, 277.5g PRIAMINE 1075 and 23.8g commercially available poly dimethyl is added dropwise
Siloxanes (trade name " KF-8010 ", Shin-Etsu Chemial Co., Ltd's manufacture), then, acyl was carried out at 140 DEG C with 10 hours
Imidization, it is the polyimide resin (A2-3) that about 70 DEG C and weight average molecular weight are about 15000 thus to obtain softening point
Solution (nonvolatile component 29.8%).It should be noted that the mol ratio of sour composition/amine component is 1.09.
Comparative example Production Example 4
BTDA-UP 190.0g, cyclohexanone 912.0g, hexahydrotoluene are put into the reaction vessel same with Production Example 1
182.4g, 60 DEG C are heated to by solution.Then, 476.0g KF-8010 is added dropwise, then, acyl was carried out with 10 hours at 140 DEG C
Imidization, it is the polyimide resin (A2-4) that about 20 DEG C and weight average molecular weight are about 35000 thus to obtain softening point
Solution (nonvolatile component 36.7%).It should be noted that the mol ratio of sour composition/amine component is 1.09.
Comparative example Production Example 5
BTDA-UP 200.0g, cyclohexanone 960.0g, hexahydrotoluene are put into the reaction vessel same with Production Example 1
192.0g, 60 DEG C are heated to by solution.Then, be added dropwise commercially available non-hydrogenated dimer diamine (trade name " PRIAMINE 1074 ",
He great Amada Co., Ltd.s manufacture) 319.2g, then, imidization reaction was carried out with 10 hours at 140 DEG C, thus obtain soft
Change the solution (nonvolatile component 29.8%) that point is the polyimides (A2-5) that about 70 DEG C and weight average molecular weight are about 25000.Need
It is noted that the mol ratio of sour composition/amine component is 1.05.
Comparative example Production Example 6
BisDA-1000 200.0g, cyclohexanone 700.0g, methyl ring are put into the reaction vessel same with Production Example 1
Hexane 175.0g, 60 DEG C are heated to by solution.Then, commercially available hydrogenation dimer diamine (trade name " PRIAMINE is added dropwise
1075 ", He great Amada Co., Ltd. manufacture) 190.5g, then, imidization reaction was carried out with 10 hours at 140 DEG C, thus
Obtain the solution (nonvolatile component that softening point is the polyimides (A2-6) that about 80 DEG C and weight average molecular weight are about 35000
29.9%).It should be noted that the mol ratio of sour composition/amine component is 1.09.
<The relative dielectric constant of polyimide resin overlay film and the measure of dielectric loss angle tangent>
Production Example and the polyimide solution for comparing Production Example are respectively coated Na Off ロ Application PTFE tapes TOMBO
On No.9001 (ニ チ ア ス Co., Ltd.), it is dried at room temperature for 12 hours, then, its solidification 1 hour is made at 200 DEG C, thus
Obtain the solidfied material piece that thickness is 50 μm.Then, for the solidfied material piece, according to JIS C2565, commercially available dielectric constant is used
The relative dielectric constant (Dk) and medium determined under device (cavity resonance type, エ ー イ ー テ ィ ー manufactures) measure 10GHz is damaged
Consume angle tangent (Df).Show the result in table 1.
[table 1]
Embodiment 1
By the solution 100.00g of (A1-1) composition, it is used as the four glycidyl group xylylene diamine (commodity of (B) composition
Name " Tetrad-X ", Mitsubishi Gas Chemical Co., Ltd's manufacture) 1.67g and hydroxyl polyphenylene oxide (trade name " SA90 ",
SABIC Co., Ltd. manufactures) 1.67g, the toluene 7.87g as (C) composition and it is used as the commercially available containing amino of (D) composition
Silane coupler (trade name " KBM603 ", Shin-Etsu Chemial Co., Ltd manufacture；N-2- (amino-ethyl) -3- aminopropans
Base trimethoxy silane) 0.07g mixing, obtain the resin combination (adhesive) that nonvolatile component is 30.0%.
Embodiment 2
By solution 100.00g, Tetrad-X 1.78g and SA901.78g of (A1-2) composition, toluene 14.78g and
KBM6030.07g is mixed, and obtains the resin combination (adhesive) that nonvolatile component is 30.0%.
Embodiment 3
By solution 25.17g, Tetrad-X 2.09g of the solution 100.00g of (A1-1) composition and (A2-3) composition and
SA902.09g, toluene 9.59g and KBM6030.08g mixing, obtain the resin combination (glue that nonvolatile component is 30.0%
Stick).
Embodiment 4
By solution 25.17g, Tetrad-X 3.32g of the solution 100.00g of (A1-1) composition and (A2-3) composition and
SA90 3.32g, toluene 15.32g and KBM603 0.09g are mixed, and obtain the resin combination that nonvolatile component is 30.0%
(adhesive).
Embodiment 5
By solution 26.76g, Tetrad-X 2.21g of the solution 100.00g of (A1-2) composition and (A2-3) composition and
SA90 2.21g, toluene 16.58g and KBM603 0.08g are mixed, and obtain the resin combination that nonvolatile component is 30.0%
(adhesive).
Embodiment 6
By the solution of the solution 30.00g of (A1-1) composition, the solution 30.82g of (A2-1) composition and (A2-3) composition
15.10g, commercially available multifunctional system's epoxy resin (trade name " jER630 ", Mitsubishi chemical Co., Ltd's manufacture；N, N- bis- shrinks
Glyceryl -4- glycidyl-oxyanilines) 1.20g and phenol resol resins (trade name " T759 ", waste river chemical industry
Co., Ltd. manufacture) 1.30g, toluene 3.81g, MEK 1.30g and KBM603 0.05g mixing, obtaining nonvolatile component is
30.0% resin combination (adhesive).
Embodiment 7
By the solution of the solution 30.00g of (A1-1) composition, the solution 30.82g of (A2-1) composition and (A2-3) composition
15.10g, jER630 0.57g and T759 0.62g, toluene 1.33g, MEK 0.62g and KBM603 0.05g mixing, are obtained
To the resin combination (adhesive) that nonvolatile component is 30.0%.
Embodiment 8
Solution 100.00g, Tetrad-X 1.67g, toluene 3.90g of (A1-1) composition are mixed, nonvolatile component is obtained
For 30.0% resin combination (adhesive).
Embodiment 9
By the solution of the solution 30.00g of (A1-1) composition, the solution 30.82g of (A2-1) composition and (A2-6) composition
15.05g, jER630 0.57g and T759 0.62g, toluene 1.37g, MEK 0.62g and KBM603 0.05g mixing, are obtained
To the resin combination (adhesive) that nonvolatile component is 30.0%.
Embodiment 10
By the solution of the solution 30.00g of (A1-1) composition, the solution 30.82g of (A2-1) composition and (A2-6) composition
15.05g, jER630 3.30g and Bis-A types cyanate (trade name " CYTESTER TA ", Mitsubishi Gas Chemical Co., Ltd's system
Make) 2.34g, toluene 8.96g, MEK 3.51g and KBM603 0.05g mixing, obtain nonvolatile component be 30.0% tree
Oil/fat composition (adhesive).
Embodiment 11
By the solution of the solution 30.00g of (A1-1) composition, the solution 30.82g of (A2-1) composition and (A2-6) composition
15.05g, jER630 0.70g and CYTESTER TA 0.49g, toluene 1.39g, MEK 0.74g and KBM603 0.05g
Mixing, obtains the resin combination (adhesive) that nonvolatile component is 30.0%.
Embodiment 12
By solution 25.17g, Tetrad-X 0.58g of the solution 100.00g of (A1-1) composition and (A2-3) composition and
SA90 0.58g, toluene 2.54g and KBM603 0.08g are mixed, and obtain the resin combination that nonvolatile component is 30.0%
(adhesive).
Comparative example 1
By solution 100.00g, Tetrad-X 1.65g and SA90 1.65g, toluene 7.05g of (A2-2) composition and
KBM603 0.07g are mixed, and obtain the resin combination (adhesive) that nonvolatile component is 30.0%.
Comparative example 2
By solution 100.00g, Tetrad-X 1.65g and SA90 1.65g, toluene 7.05g of (A2-3) composition and
KBM603 0.07g are mixed, and obtain the resin combination (adhesive) that nonvolatile component is 30.0%.
Comparative example 3
By the solution 20.00g of (A1-1) composition and (A2-3) composition 80.54g, Tetrad-X 1.67g and SA90
1.67g, toluene 7.47g and KBM603 0.07g are mixed, and obtain the resin combination that nonvolatile component is 30.0% (gluing
Agent).
Comparative example 4
By the solution 100.00g of (A1-1) composition and (A2-3) composition 25.17g, Tetrad-X 6.26g and SA90
6.26g, toluene 29.00g and KBM603 0.09g are mixed, and obtain the resin combination that nonvolatile component is 30.0% (gluing
Agent).
Comparative example 5
By the solution 100.00g of (A1-1) composition and (A2-3) composition 25.17g, Tetrad-X 0.19g and SA90
0.19g, toluene 0.71g and KBM603 0.08g are mixed, and obtain the resin combination that nonvolatile component is 30.0% (gluing
Agent).
Comparative example 6
By solution 100.00g, Tetrad-X 2.04g and SA90 2.04g, toluene 32.04g of (A2-4) composition and
KBM603 0.08g are mixed, and obtain the resin combination (adhesive) that nonvolatile component is 30.0%.
Comparative example 7
By solution 100.00g, Tetrad-X 1.66g and SA90 1.66g, toluene 7.26g of (A2-5) composition and
KBM603 0.07g are mixed, and obtain the resin combination (adhesive) that nonvolatile component is 30.0%.
<The making of sheet adhesive>
By the adhesive of embodiment 1 to make dried thickness be applied to support using gap coating machine in the way of 10 μm
Piece (trade name " カ プ ト Application 100EN ", Dong Li-Dupont Kabushiki Kaisha's manufacture；25 μm of thickness；Thermal coefficient of expansion：15ppm/℃)
On, then, dried 3 minutes at 180 DEG C, thus obtain sheet adhesive.For other embodiment and the adhesive of comparative example, also together
Obtain sheet adhesive sample.
Then, by minute surface of the thickness for 18 μm of electrolytic copper foil (trade name " F2-WS ", the manufacture of Furukawa copper foil Co., Ltd.)
Stress to be laminated on the gluing surface of each sheet adhesive, heating compacting is carried out under conditions of pressure 1MPa, 180 DEG C and 30 minutes, thus
Make layered product.For the adhesive of comparative example 1, layered product is similarly obtained.
<The relative dielectric constant of adhesive layer and the measure of dielectric loss angle tangent>
The adhesive of embodiment and comparative example about 7g is injected separately into fluororesin PFA plates (diameter 75mm, Co., Ltd.
Manufactured by mutual Physicochemical nitre makes), 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, under conditions of 180 DEG C × 12 hours solidify it, thus obtain the solidfied material that thickness is about 300 μm
Piece.Then, for the solidfied material piece, according to JIS C2565, using commercially available Dielectric Coefficient device (cavity resonance type,
エ ー イ ー テ ィ ー manufacture) determine 10GHz under relative dielectric constant (Dk) and dielectric loss angle tangent (Df).
<Adhesive test>
For embodiment and each layered product of comparative example, according to JIS C-6481, (flexible printing wiring board is with copper-clad laminated
Plate test method) determine peel strength (N/cm).
<Soldering heat resistant test>
For embodiment and each layered product of comparative example, after hardening, in 288 DEG C of pricker in the way of making copper foil side under
Floated 30 seconds in welding bath, confirmation whether there is cosmetic variation.Unconverted situation is denoted as zero, the situation for having foaming, heaving is denoted as
×。
[table 2]
<The making of bonding sheet>
The adhesive of embodiment 1 is de- to make dried thickness be applied in the way of about 25 μm using gap coating machine
On mould film (trade name " WH52-P25CM (white) ", the manufacture of サ Application エ-Hua Yan Co., Ltd.), then, 5 points are dried at 150 DEG C
Clock, thus obtains bonding sheet.For other embodiment and the adhesive of comparative example, bonding sheet is similarly obtained.
<The making of printed wiring board>
Line width/line-spacing=0.2/0.2 (mm) resist is formed on the copper foil on the two sides of the copper-clad laminated board of embodiment 1
Pattern, gains is impregnated in the ferric chloride in aqueous solution that concentration is 40%, is thus etched, form copper circuit.So, obtain
To printed wiring board.
<The making of multiwiring board>
Using resulting printed wiring board as core, the copper foil of the resin of overlapping embodiment 1 on its two sides, in pressure
Crimped under conditions of 4.5MPa, 200 DEG C and 30 minutes, line width/line is formed on the untreated copper foil of the outer layer of gains
Resist patterns away from=0.2/0.2 (mm).Then, by resulting substrate by being impregnated in the chlorination molten iron that concentration is 40%
It is etched in solution, is consequently formed copper circuit.Overlapping above-mentioned sheet adhesive on the top layer of copper circuit is formed with this, in pressure
Heating compacting is carried out under conditions of 1MPa, 180 DEG C and 30 minutes, is thus laminated.So, obtain possessing 4 circuit patterns
The multiwiring board of layer.
<The making 2 of printed wiring board>
Line width/line-spacing=0.2/0.2 (mm) resist figure is formed on the copper foil of the one side copper-clad laminated board of embodiment 1
Case, gains is impregnated in the ferric chloride in aqueous solution that concentration is 40%, is thus etched, form copper circuit.Prepare identical
Printed wiring board, above-mentioned bonding sheet is sandwiched between the substrate side without copper circuit, pressure 1MPa, 180 DEG C and 30 minutes
Under conditions of carry out heating compacting, be thus laminated.Then, have overlapping above-mentioned on the top layer of copper circuit in the formation of layered product
Sheet adhesive, heating compacting is carried out under conditions of pressure 1MPa, 180 DEG C and 30 minutes, is thus laminated.So, had
The multiwiring board of standby 4 circuit pattern layers.
For the adhesive of other embodiment, printed wiring board and multiwiring board are obtained also by same method.
Claims (20)
1. a kind of resin combination, it includes the aromatic tetracarboxylic acid's dianhydride for making the content containing free carboxy acid be less than 1 weight %
(a1) and hydrogenation dimer diamine (a2) and without diamino polysiloxane (a3) monomer group (1) reaction formed by polyimides
(A1)。
2. resin combination as claimed in claim 1, wherein, aromatic tetracarboxylic acid's dianhydride as (a1) composition is by following structural tables
Show,
In formula, X represents singly-bound ,-SO2-、-CO-、-O-、-O-C6H4-C(CH3)2-C6H4- O- or-COO-Y-OCO-, wherein, Y tables
Show-(CH2)l- or-H2C-HC (- O-C (=O)-CH3)-CH2-, l=1~20.
3. such as resin combination of claim 1 or 2, wherein, the mol ratio of (a1) composition and (a2) composition in (1) composition
[(a1)/(a2)] is 1~1.5.
4. such as resin combination according to any one of claims 1 to 3, wherein, further containing poly- beyond (A1) composition
Acid imide (A2).
5. resin combination as claimed in claim 4, it is characterised in that (A2) composition is to make containing (a1) composition and/or free carboxylic
The content of acid is more than 1 weight % aromatic tetracarboxylic acid's dianhydride (a1 ') and (a2) composition and/or non-hydrogenated dimer diamine
Polyimide resin formed by monomer group (2) reaction of (a2 ').
6. resin combination as claimed in claim 5, wherein, (2) composition further contains (a3) composition.
7. the resin combination as any one of claim 4~6, wherein, the solid of (A1) composition and (A2) composition into
It is 40/60~99/1 to divide weight ratio [(A1)/(A2)].
8. such as resin combination according to any one of claims 1 to 7, wherein, further containing crosslinking agent (B).
9. resin combination as claimed in claim 8, wherein, (B) composition is polyepoxy compound (B1) and/or polyphenylene ether compound
(B2)。
10. resin combination as claimed in claim 9, wherein, (B1) composition is the four glycidyl group xyxylene of following structures
Diamines,
In formula, Z1Represent phenylene or cyclohexylidene.
11. such as resin combination of claim 9 or 10, wherein, (B2) composition is the polyphenylene oxide of the hydroxyl of following structures,
In formula, Z2The alkylidene or singly-bound of carbon number 1~3 are represented, m represents that 0~20, n represents 0~20, m and n total expression
1~30.
12. the resin combination as any one of claim 1~11, wherein, further containing organic solvent (C).
13. the resin combination as any one of claim 1~12, wherein, further contain formula：Q-Si(R1)a
(OR2)3-aIn shown reactive polyglycidyl compounds (D), formula, Q is represented containing the functional group reacted with anhydride group
Group, R1Represent the alkyl of hydrogen or carbon number 1~8, R2The alkyl of carbon number 1~8 is represented, a represents 0,1 or 2.
14. a kind of adhesive, it includes the resin combination any one of claim 1~13.
15. a kind of membranaceous adhesive material, it is made up of the solidfied material of the adhesive of claim 14.
16. a kind of sheet adhesive, it is used as adhesive layer using the solidfied material of the adhesive of claim 14.
17. a kind of multiwiring board, it uses the adhesive being selected from by claim 14, the membranaceous adhesive material of claim 15
At least one of group constituted with the sheet adhesive of claim 16 and obtain.
18. a kind of copper foil of resin, it uses the adhesive being selected from by claim 14, the membranaceous gluing material of claim 15
Expect at least one of group constituted with the sheet adhesive of claim 16 and obtain.
19. a kind of copper-clad laminated board, its usage right requires the copper foil of 18 resin and obtained.
20. a kind of printed wiring board, its usage right requires 19 copper-clad laminated board and obtained.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015194163 | 2015-09-30 | ||
| JP2015-194163 | 2015-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106977716A true CN106977716A (en) | 2017-07-25 |
Family
ID=58583468
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610874044.6A Pending CN106977716A (en) | 2015-09-30 | 2016-09-30 | Resin combination, adhesive, membranaceous adhesive material, sheet adhesive, the copper foil of resin, copper-clad laminated board, wiring plate |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR102524336B1 (en) |
| CN (1) | CN106977716A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109575282A (en) * | 2017-09-29 | 2019-04-05 | 日铁化学材料株式会社 | The manufacturing method of polyimides |
| CN110505767A (en) * | 2019-07-08 | 2019-11-26 | 苏州固泰新材股份有限公司 | A kind of copper foil base material and preparation method thereof |
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| JPH09136958A (en) * | 1995-11-16 | 1997-05-27 | Hitachi Chem Co Ltd | Production of polyimide resin particle |
| CN1768089A (en) * | 2003-04-18 | 2006-05-03 | 株式会社钟化 | Thermosetting resin composition, multilayer body using same, and circuit board |
| CN1938357A (en) * | 2004-04-19 | 2007-03-28 | 株式会社钟化 | Thermosetting resin composition, laminated body using it, and circuit board |
| CN102209754A (en) * | 2008-11-10 | 2011-10-05 | 味之素株式会社 | Resin composition for printed wiring board |
| CN103289633A (en) * | 2012-02-24 | 2013-09-11 | 荒川化学工业株式会社 | Polyimide-based adhesive composition, cured product, adhesive sheet, laminate, and flexible printed circuit board |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3111441B2 (en) | 1993-11-30 | 2000-11-20 | 宇部興産株式会社 | Substrate for printed wiring board |
| JP5534378B2 (en) | 2012-02-24 | 2014-06-25 | 荒川化学工業株式会社 | Polyimide adhesive composition, cured product, adhesive sheet, laminate, flexible printed circuit board |
-
2016
- 2016-09-30 KR KR1020160126360A patent/KR102524336B1/en active IP Right Grant
- 2016-09-30 CN CN201610874044.6A patent/CN106977716A/en active Pending
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|---|---|---|---|---|
| JPH09136958A (en) * | 1995-11-16 | 1997-05-27 | Hitachi Chem Co Ltd | Production of polyimide resin particle |
| CN1768089A (en) * | 2003-04-18 | 2006-05-03 | 株式会社钟化 | Thermosetting resin composition, multilayer body using same, and circuit board |
| CN1938357A (en) * | 2004-04-19 | 2007-03-28 | 株式会社钟化 | Thermosetting resin composition, laminated body using it, and circuit board |
| CN102209754A (en) * | 2008-11-10 | 2011-10-05 | 味之素株式会社 | Resin composition for printed wiring board |
| CN103289633A (en) * | 2012-02-24 | 2013-09-11 | 荒川化学工业株式会社 | Polyimide-based adhesive composition, cured product, adhesive sheet, laminate, and flexible printed circuit board |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109575282A (en) * | 2017-09-29 | 2019-04-05 | 日铁化学材料株式会社 | The manufacturing method of polyimides |
| CN110505767A (en) * | 2019-07-08 | 2019-11-26 | 苏州固泰新材股份有限公司 | A kind of copper foil base material and preparation method thereof |
| CN110505767B (en) * | 2019-07-08 | 2021-03-30 | 苏州固泰新材股份有限公司 | Flexible copper foil base material and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20170038740A (en) | 2017-04-07 |
| KR102524336B1 (en) | 2023-04-20 |
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Application publication date: 20170725 |