CN114685788A - 化合物、树脂组合物、及积层板 - Google Patents
化合物、树脂组合物、及积层板 Download PDFInfo
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- CN114685788A CN114685788A CN202110435689.0A CN202110435689A CN114685788A CN 114685788 A CN114685788 A CN 114685788A CN 202110435689 A CN202110435689 A CN 202110435689A CN 114685788 A CN114685788 A CN 114685788A
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- Prior art keywords
- anhydride
- resin composition
- compound
- bis
- dianhydride
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 80
- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
- 239000011888 foil Substances 0.000 claims abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 6
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 5
- 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 description 29
- -1 diamine compound Chemical class 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 150000008064 anhydrides Chemical class 0.000 claims description 17
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 16
- 239000011889 copper foil Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 150000008065 acid anhydrides Chemical class 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 9
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001843 C4-C10 alkenyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 claims description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 3
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 3
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 claims description 3
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 3
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 3
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 claims description 3
- RYYUUQPLFHRZOY-UHFFFAOYSA-N 4-[2-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1OC1=CC=C(N)C=C1 RYYUUQPLFHRZOY-UHFFFAOYSA-N 0.000 claims description 3
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 claims description 3
- YGQZOUHXUGYNPH-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)-3-methylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(C)=CC=1OC1=CC=C(N)C=C1 YGQZOUHXUGYNPH-UHFFFAOYSA-N 0.000 claims description 3
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- QQYNRBAAQFZCLF-UHFFFAOYSA-N furan-maleic anhydride adduct Chemical compound O1C2C3C(=O)OC(=O)C3C1C=C2 QQYNRBAAQFZCLF-UHFFFAOYSA-N 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- 125000005591 trimellitate group Chemical group 0.000 claims description 3
- JSSSSGRNRZNMKP-UHFFFAOYSA-N (4-aminophenyl) benzenesulfonate Chemical compound C1=CC(N)=CC=C1OS(=O)(=O)C1=CC=CC=C1 JSSSSGRNRZNMKP-UHFFFAOYSA-N 0.000 claims description 2
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 claims description 2
- ZWQOXRDNGHWDBS-UHFFFAOYSA-N 4-(2-phenylphenoxy)aniline Chemical group C1=CC(N)=CC=C1OC1=CC=CC=C1C1=CC=CC=C1 ZWQOXRDNGHWDBS-UHFFFAOYSA-N 0.000 claims description 2
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 claims description 2
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 claims 1
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 claims 1
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 11
- 238000010521 absorption reaction Methods 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 9
- 229910052751 metal Inorganic materials 0.000 abstract description 8
- 239000002184 metal Substances 0.000 abstract description 8
- 125000002947 alkylene group Chemical group 0.000 abstract description 7
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 40
- 239000010410 layer Substances 0.000 description 28
- 229920001721 polyimide Polymers 0.000 description 18
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000004642 Polyimide Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 10
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
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- 150000004985 diamines Chemical class 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000620 organic polymer Polymers 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
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- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 2
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- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- DDOQBQRIEWHWBT-UHFFFAOYSA-N 2-azaniumyl-4-phosphonobutanoate Chemical compound OC(=O)C(N)CCP(O)(O)=O DDOQBQRIEWHWBT-UHFFFAOYSA-N 0.000 description 1
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
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- 239000003963 antioxidant agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- OUTSZJJKRARFTP-UHFFFAOYSA-N benzene 4-phenoxyaniline Chemical compound C1=CC=CC=C1.NC1=CC=C(OC2=CC=CC=C2)C=C1 OUTSZJJKRARFTP-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
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- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005817 fluorobutyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
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Abstract
本发明涉及一种化合物、包含该化合物的树脂组合物、及包含该树脂组合物的固化物的积层板。该化合物具有式(I)所示结构:其中,A1是C24‑48的亚烷基、C24‑48的亚烯基、C24‑48的亚炔基、C24‑48的脂环亚烷基、C24‑48的脂环亚烯基、或C24‑48的脂环亚炔基;A2是C2‑12亚烷基、C6‑C25亚芳基、C4‑8亚环烷基、C5‑25亚杂芳基、二价C7‑C25烷基芳基、二价C7‑25酰基芳基、二价C6‑25芳醚基、或二价C7‑25酰氧基芳基;以及,n≧1。由于该树脂组合物包含该具有特定结构的化合物以及特定的成份比例,因此由该树脂组合物制备的膜层(固化物)除了在高频(10GHz以上的频段)具有低介电常数(Dk)及低介电损失(Df)以及在吸湿后仍可维持稳定介电性质外,可以进一步涂布于金属箔基材上,并保有良好的接合强度、耐热性及耐化性。
Description
技术领域
本揭露关于一种化合物、树脂组合物、及积层板。
背景技术
随着高频高速传输应用的需求日渐殷切,电子产品的数据处理速度以及通讯速度趋向高频高速化,电路板(PCB)材料的要求规格亦逐渐升级。聚酰亚胺(polyimide,PI)树脂由于具有优异的热安定性及良好的机械、电气及化学性质,被广泛地应用于印刷电路板。然而,传统聚酰亚胺树脂中因含有具极性的酰亚胺骨架,使其固化物吸水率变高,进而导致在较高湿度的使用环境下,聚酰亚胺树脂固化物的介电损耗(Df)也随之增加。此外,虽然降低铜箔的表面粗糙度,可以降低传输损耗,而符合高频信号传输的需求。然而,当铜箔具有更低的表面粗糙度虽然可减少高频信号传输损耗,但会使铜箔和电路基板之间的接合强度降低,从而导致铜箔容易从电路基板剥离并降低印刷电路板的信赖度。液晶型高分子(liquidcrystal polymer、LCP)因具低介电常数及低损耗因子等特性,已被运用在高频电路板。然而,液晶型高分子膜层对于铜箔的接着力不佳,容易由铜箔上剥离(peeling)。
发明内容
本揭露提供一种化合物。根据本揭露实施例,该化合物具有式(I)所示结构:
其中,A1可为C24-48的亚烷基(alkylene group)、C24-48的亚烯基(alkenylenegroup)、C24-48的亚炔基(alkynylene group)、C24-48的脂环亚烷基(alicyclic alkylenegroup)、C24-48的脂环亚烯基(alicyclic alkenylene group)、或C24-48的脂环亚炔基(alicyclic alkynylene group);A2可为C2-12亚烷基(alkylene group)、C6-C25亚芳基(arylene group)、C4-8亚环烷基(cycloalkylene group)、C5-25亚杂芳基(heteroarylenegroup)、二价C7-C25烷基芳基(alkylaryl group)、二价C7-25酰基芳基(acylaryl group)、二价C6-25芳醚基(aryl ether group)、或二价C7-25酰氧基芳基(acyloxyaryl group);以及,n≧1。
根据本揭露实施例,本揭露提供一树脂组合物。根据本揭露实施例,该树脂组合物包含上述化合物、以及一酸酐,其中该酸酐包含单酸酐、二酸酐、或上述的组合。
根据本揭露实施例,本揭露亦提供一种积层板。根据本揭露实施例,该积层板包含一导电层,具有一表面;以及,一膜层。该膜层配置于该导电层的表面,其中该膜层包含上述树脂组合物的固化物。
附图说明
图1为本揭露实施例所述积层板的示意图;
其中,符号说明:
10 导电层 11 上表面
13 下表面 20 膜层
100 积层板。
具体实施方式
以下针对本揭露的聚合物及光敏性树脂组合物作详细说明。应了解的是,以下的叙述提供许多不同的实施例或例子,用以实施本揭露的不同样态。以下所述特定的组件及排列方式仅为简单描述本揭露。当然,这些仅用以举例而非本揭露的限定。
再者,说明书与权利要求中所使用的序数例如”第一”、”第二”、”第三”等的用词,以修饰权利要求的组件,其本身并不意含及代表该请求组件有任何的前的序数,也不代表某一请求组件与另一请求组件的顺序、或是制造方法上的顺序,该些序数的使用仅用来使具有某命名的一请求组件得以和另一具有相同命名的请求组件能作出清楚区分。
本揭露提供一种化合物、树脂组合物、及积层板。根据本揭露实施例,该树脂组合物可用来制备聚酰亚胺膜层(或聚胺酯-聚酰亚胺膜层)。由于该树脂组合物包含该具有特定结构的化合物以及特定的成份比例,因此由该树脂组合物制备的膜层(固化物)除了在高频(10GHz以上的频段)具有低介电常数(Dk)及低介电损失(Df)以及在吸湿后仍可维持稳定介电性质外,可以进一步涂布于金属箔基材上,并保有良好的接合强度、耐热性及耐化性。
根据本揭露实施例,该化合物可具有式(I)所示结构:
其中,A1可为C24-48的亚烷基(alkylene group)、C24-48的亚烯基(alkenylenegroup)、C24-48的亚炔基(alkynylene group)、C24-48的脂环亚烷基(alicyclic alkylenegroup)、C24-48的脂环亚烯基(alicyclic alkenylene group)、或C24-48的脂环亚炔基(alicyclic alkynylene group)。A2可为C2-12亚烷基(alkylene group)、C6-C25亚芳基(arylene group)、C4-8亚环烷基(cycloalkylene group)、C5-25亚杂芳基(heteroarylenegroup)、二价C7-C25烷基芳基(alkylaryl group)、二价C7-25酰基芳基(acylaryl group)、二价C6-25芳醚基(aryl ether group)、或二价C7-25酰氧基芳基(acyloxyaryl group)。n可大于或等于1,例如1、2、3、4、5、6、7、8、9、10、15、20、25、30或50。根据本揭露实施例,A1及A2碳上的氢,可视需要被氟、C1-6烷基、或C1-6氟烷基取代。
根据本揭露实施例,该第一重复单元中的A1可为直链(linear)、分枝(branched)、或分枝环状(branched cyclic)的基团,且A1的化学式可为-CnH2n-、-CnH2(n-1)-、-CnH2(n-2)-、-CnH2(n-3)-、-CnH2(n-4)-、-CnH2(n-5)-、或-CnH2(n-6)-,其中n为24至48(例如25、26、27、28、29、30、31、32、33、34、35、36、37、38、39、40、41、42、43、44、45、46、或47)。
其中A1是以星号(*)所标示位置与氧连接。12≥a≥4;12≥b≥4;R2各自独立为氢、C4-10烷基、C4-10烯基、或C4-10炔基;至少两个R2不为氢;以及,A1具有24至48个碳。根据本揭露实施例,在A1中,至少两个R2不为氢(即至少两个R2各自为C4-10烷基、C4-10烯基、或C4-10炔基)。根据本揭露实施例,在A1中,至少三个R2不为氢(即至少三个R2各自为C4-10烷基、C4-10烯基、或C4-10炔基)。根据本揭露实施例,A1可为
根据本揭露实施例,该A2可为 其中A2是以星号(*)所标示位置与氮连接。Y可为-O-、-C(R1)2-、 R1可各自独立为氢、氟、C1-6烷基、或C1-6氟烷基;以及,m可为2、3、4、5、6、7、或8。
根据本揭露实施例,本揭露所述C1-10烷基可为直链或分支(linear or branched)链的烷基。举例来说,C1-10烷基可为甲基(methyl)、乙基(ethyl)、丙基(propyl)、丁基(butyl)、戊基(pentyl)、己基(hexyl)、庚基(heptyl)、辛基(octyl)、或其异构体(isomer)。根据本揭露实施例,本揭露所述C1-6氟烷基是指碳上的氢全部或部份被氟取代的烷基,且可为直链(linear)或分支键(branched),例如氟甲基、氟乙基、氟丙基、氟丁基、氟戊基、氟己基、或其异构体(isomer)。在此,本揭露所述氟甲基可为单氟甲基、二氟甲基、或全氟甲基,而氟乙基可为单氟乙基、二氟乙基、三氟乙基、四氟乙基、或全氟乙基。
根据本揭露实施例,本揭露所述亚烷基可为直链或分枝(linear or branched)的亚烷基。根据本揭露实施例,本揭露所述烯基可为直链或分枝(linear or branched)的烯基。根据本揭露实施例,本揭露所述炔基可为直链或分枝(linear or branched)的炔基。
根据本揭露实施例,本揭露所述化合物可由一二元醇与一二异氰酸酯(diisocyanate)反应所得。根据本揭露实施例,该二元醇的化学式可为CnH2(n+1)O2、CnH2(n)O2、CnH2(n-1)O2、CnH2(n-2)O2、CnH2(n-3)O2、CnH2(n-4)O2、或CnH2(n-5)O2-,其中n可为24至48(例如25、26、27、28、29、30、31、32、33、34、35、36、37、38、39、40、41、42、43、44、45、46、或47)。举例来说,该二元醇为
根据本揭露实施例,该二异氰酸酯(diisocyanate)可为 其中Y可为-O-、-C(R1)2-、 R1可各自独立为氢、氟、C1-6烷基、或C1-6氟烷基;以及,m可为2、3、4、5、6、7、或8。根据本揭露实施例,该二异氰酸酯(diisocyanate)可为五亚甲基二异氰酸酯(pentamethylene diisocyanate)、六亚甲基二异氰酸酯(hexamethylene diisocyanate,HDI)、二异氰酸二苯甲烷(4,4'-methylenediphenyl diisocyanate,MDI)、4,4'-亚甲基二苯基二异氰酸酯(4,4'-methylenedicyclohexyl diisocyanate,H12MDI)、2,4-甲苯二异氰酸酯(2,4-toluenediisocyanate)、2,5-甲苯二异氰酸酯(2,5-toluene diisocyanate)、2,6-甲苯二异氰酸酯等(2,6-toluene diisocyanate)、二异氰酸异佛尔酮(isophorone diisocyanate,IPDI)、1,5-萘基二异氰酸酯(1,5-naphthalene diisocyanate,NDI)、对-亚苯基二异氰酸酯(p-phenylene diisocyanate,PPDI)、二甲苯二异氰酸酯(xylylene diisocyanate,XDI)、氢化1,4-二甲苯二异氰酸酯(hydrogenated 1,4-xylylene diisocyanate,1,4-H6XDI)、或三甲基六亚甲基二异氰酸酯(trimethyl hexamethylene diisocyanate,TMDI)。根据本揭露实施例,该二异氰酸酯与该二元醇的摩尔比可为约1.05至2。
根据本揭露实施例,本揭露亦提供一种树脂组合物,可用来制备一聚酰亚胺膜层或聚胺酯-聚酰亚胺膜层。根据本揭露实施例,该树脂组合物包含本揭露所述具有式(I)的化合物;以及,一酸酐。根据本揭露实施例,该酸酐包含单酸酐、二酸酐、或上述的组合。
根据本揭露实施例,该单酸酐可为马来酸酐(maleic anhydride)、琥珀酸酐(succinic anhydride)、苯乙烯马来酸酐(styrene maleic anhydride)、5-原冰片烯-2,3-二羧酸酐(5-norbornene-2,3-dicarboxylanhydride)、3,6-环氧-1,2,3,6-四氢酞酸酐(3,6-epoxy-1,2,3,6-tetra hydrophthalicanhydride)、3,4,5,6-四氢邻苯二甲酐(3,4,5,6-tetrahydrophthalic anhydride)、邻苯二甲酐(phthalic anhydride)、1,2,3,6-四氢邻苯二甲酐(1,2,3,6-tetrahydrophthalic anhydride)、衣康酸酐(itaconic anhydride,IA)、柠康酸酐(citraconic anhydride,CA)、或2,3-二甲基马来酸酐(2,3-dimethylmaleicanhydride,DMMA)。根据本揭露实施例,该二酸酐可为 其中Z是单键、-O-、-SO2-、-C(CH3)2-、-C(CF3)2-、 以及,R3各自独立为氢、C1-6烷基、或C1-6氟烷基。根据本揭露实施例,该二酸酐可为苯均四酸二酐(pyromellitic dianhydride、PMDA)、4,4'-六氟异亚丙基二苯二甲酸二酐(4,4'-(hexafluoroisopropylidene)-diphthalic anhydride、6FDA)、4,4'-氧二醚酸酐(4,4'-oxydiphthalic anhydride、ODPA)、3,3',4,4'-联苯四甲酸二酐(3,3',4,4'-Biphenyltetracarboxylic dianhydride、BPDA)、4,4'-双酚A二酐(4,4'-bisphenol A dianhydride、BPADA)、对苯基二(偏苯三酸酯)二酸酐(p-phenylene bis(trimellitate)dianhydride、TAHQ)、或对苯二酚二酞酸酐(hydroquinnone diphtalicanhydride、HQDA)。
根据本揭露实施例,该酸酐可为单酸酐,因此该树脂组合物包含具有式(I)的化合物以及单酸酐。该酸酐可具有一摩尔数M1,以及该化合物具有一摩尔数M2,其中1.5≤M2/M1≤2.5。根据本揭露实施例,由该树脂组合物所制备的化合物可为其中A1、A2、以及n的定义与上述相同;以及,A3可为单酸酐脱氧所得的残基,且该A3以两个羰基与氮连接。举例来说,由该树脂组合物所制备的化合物可为(即所使用的单酸酐为马来酸酐)。
根据本揭露实施例,该酸酐可为二酸酐,因此该树脂组合物包含具有式(I)的化合物以及二酸酐。根据本揭露实施例,该酸酐可具有一摩尔数M1,以及该化合物具有一摩尔数M2,其中0.05≤M2/M1≤1。根据本揭露实施例,由该树脂组合物所制备的聚酰亚胺可具有一重复单元,其中该重复单元的结构可为其中A1、A2、以及n的定义与上述相同;以及,A4可为 其中A4以星号(*)所标示位置与羰基连接。Z是单键、-O-、-SO2-、-C(CH3)2-、-C(CF3)2-、 以及,R3可为氢、氟、C1-6烷基、或C1-6氟烷基。
根据本揭露实施例,当该酸酐是单酸酐及二酸酐的组合时,该酸酐具有一摩尔数M1、而该化合物具有一摩尔数M2,其中0.05≤M2/M1≤3,且该单酸酐及该二酸酐的摩尔比可为1:99至99:1。
根据本揭露实施例,当该树脂组合物包含具有式(I)的化合物以及二酸酐时,该树脂组合物可更包含一二胺化合物。根据本揭露实施例,该酸酐(即二酸酐)具有一摩尔数M1、该化合物具有一摩尔数M2、以及该二胺化合物具有一摩尔数M3,其中0.5≤(M2+M3)/M1≤3。此外,根据本揭露实施例,0.05≤M2/(M2+M3)≤0.3。当M2/(M2+M3)的值过低,则由所得的树脂组合物制备的膜层(固化物)与金属箔基材的接合度会变明显变差。当M2/(M2+M3)的值过高,则由所得的树脂组合物制备的膜层(固化物)其耐化性变差。根据本揭露实施例,由该树脂组合物所制备的聚合物(例如聚胺酯-聚酰亚胺)可具有一第一重复单元及一第二重复单元,其中该第一重复单元的结构可为而该第二重复单元的结构可为其中A1、A2、A4、以及n的定义与上述相同;以及,A5可为 其中A5以星号(*)所标示位置与氮(可为第一重复单元或第二重复单元的氮)连接。W可为-O-、-C(CH3)2-、-C(CF3)2-、 以及,R4可为氢、氟、C1-6烷基、或C1-6氟烷基。根据本揭露实施例该第一重复单元及第二重复单元的数目比可为1:19至3:7。当第一重复单元及第二重复单元的数目比过低,则由所得的树脂组合物制备的膜层(固化物)与金属箔基材的接合度会明显变差。当第一重复单元及第二重复单元的数目比过高,则由所得的树脂组合物制备的膜层(固化物)其耐化性变差。
根据本揭露实施例,该二胺化合物可为 其中W可为-O-、-C(CH3)2-、-C(CF3)2-、 以及,R4可为氢、氟、C1-6烷基、或C1-6氟烷基。根据本揭露实施例,该二胺化合物可为间联甲苯胺(m-tolidine、m-TB)、间二氨基苯(m-phenylenediamine、m-PDA),对二氨基苯(p-phenylenediamine,p-PDA)、4,4'-二氨基二苯醚(4,4'-oxydianiline、4,4'-ODA),3,4'-二氨基二苯醚(3,4'-oxydianiline、3,4'-ODA)、1,4-双(4-氨苯氧基)苯(1,4-bis(4-aminophenoxy)benzene、TPE-Q)、1,3-双(4-氨苯氧基)苯(1,3-bis(4-aminophenoxy)benzene、TPE-R)、1,2-双(4-氨苯氧基)苯(1,2-bis(4-aminophenoxy)benzene、1,2-APB)、1,3-双(3-氨苯氧基)苯(1,3-bis(3-aminophenoxy)benzene、APB-133)、2,5-双(4-氨苯氧基)甲苯)(2,5-bis(4-aminophenoxy)toluene)、双(4-[4-氨基苯氧基]苯)醚(Bis(4-[4-aminophenoxy]phenyl)ether、BAPE)、4,4'-二(4-氨基苯氧基)联苯(4,4'-bis[4-aminophenoxy]biphenyl、BAPB)、2,2'-双[4-(4-氨基苯氧基苯基)]丙烷(2,2-bis[4-(4-aminophenoxy)]phenyl propane、BAPP)、4,4'-双(4-氨基苯氧基)苯砜(bis-(4-(4-aminophenoxy)phenyl sulfone、BAPS)、2,2'-双(三氟甲基)-4,4'-二氨基联苯(2,2'-bis(trifluoromethyl)4,4'-diaminobiphenyl、TFMB)、1,4-苯二胺(1,4-diaminobenzene、PPD)、或上述的混合。
根据本揭露实施例,当该树脂组合物同时包含具有式(I)的化合物、单酸酐、及二酸酐时,该树脂组合物可更包含一二胺化合物。根据本揭露实施例,该酸酐(即单酸酐及二酸酐)可具有一摩尔数M1、该化合物具有一摩尔数M2、以及该二胺化合物具有一摩尔数M3,其中0.5≤(M2+M3)/M1≤3。根据本揭露实施例,由该树脂组合物所制备的聚合物(例如聚胺酯-聚酰亚胺)的结构可为
其中A1、A2、A3、A4、A5、以及n的定义与上述相同、i≥1(例如100≥i≥1)、j≥1(例如100≥j≥1)、以及i:j可为1:19至19:1。根据本揭露实施例,重复单元以及重复单元可以无规方式或嵌段方式重复。根据本揭露实施例,由该树脂组合物所制备的聚合物可为
根据本揭露实施例,该树脂组合物可进一步包含一有机高分子材料,以改善由树脂组合物所得的固化物的机械强度以及耐化性。其中,该有机高分子材料为环氧树脂、酚醛树脂、碳氢树脂、丙烯酸树脂、聚酰胺、聚亚酰胺、聚甲基丙烯酸甲酯、聚乙烯四氢咯酮烷酮、聚苯乙烯、或聚偏二氟乙烯。根据本揭露实施例,该有机高分子材料的含量可为约0.5wt%至150wt%,以本揭露所述该聚合物及该酸酐的总重为基准。
根据本揭露实施例,本揭露所述树脂组合物可视需要更包含其他成分,例如本领域习知的添加剂,以改良树脂组合物其固化物的物化性质。所述习知添加剂的实例包括但不限于:阻燃剂、粘度调节剂、触变剂(thixotropic agent)、消泡剂、调平剂(levelingagent)、表面处理剂、安定剂、及抗氧化剂。所述添加剂可单独使用或组合使用。上述各种添加剂的用量,为本揭露所属技术领域中具有通常知识者于观得本揭露的揭露内容后,可依其通常知识而视需要调整者,并无特殊限制。
根据本揭露实施例,本揭露所述树脂组合物的各成份,包含本揭露所述化合物及酸酐(或更包含二胺、有机高分子材料、及添加剂)可进一步溶于一溶剂中,以调整树脂组合物的粘度,促使该树脂组合物藉由一涂布制程在一基材上形成一涂层。所述溶剂可为任何可溶解或分散粘着剂组合物各成分、但不与该等成分反应的惰性溶剂。举例言之,可用以溶解或分散粘着剂组合物各成分的溶剂包含但不限于:二甲苯(xylene)、甲苯(toluene)、四甲基苯、甲基异丁基酮、甲基乙基酮、乳酸乙酯或环己烯酮、N-甲基-2-吡咯烷酮(N-methyl-2-pyrrolidone、NMP)、丁酮(methyl ethyl ketone、MEK)、N,N-二甲基乙酰胺(N,N-dimethylacetamide、DMAc)、γ-丁内酯(γ-butyrolactone、GBL)、N,N-二甲基甲酰胺(N,N-Dimethylformamide、DMF)、或二甲基亚砜(dimethyl sulfoxide、DMSO)。各溶剂可单独使用或任意组合使用。溶剂的用量并无特殊限制,原则上只要能使树脂组合物各成分均匀溶解或分散于其中即可。该树脂组合物的涂布方式可为网印、旋转涂布法(spin coating)、棒状涂布法(bar coating)、刮刀涂布法(blade coating)、滚筒涂布法(roller coating)、浸渍涂布法(dip coating)、喷涂(spray coating)、或刷涂(brush coating)。
根据本揭露实施例,本揭露亦提供一种积层板。请参照图1,为本揭露一本揭露实施例所述的积层板100的示意图。如图1所示,该积层板100包含一导电层10(具有上表面11及下表面13)、以及一膜层20配置于该导电层10的上表面11,其中该膜层20是由上述的树脂组合物经一固化制程后所制得(即该膜层为该树脂组合物的固化产物)。
根据本揭露实施例,该导电层包括但不限于导电金属箔。导电金属箔包括但不限于铜箔、镍箔或铝箔。导电层厚度一般而言可为约0.1微米至约100微米,但本发明不限于此。导电金属箔片的表面可为光滑的或者可经粗化而具有粗糙表面。根据本揭露实施例,该导电层的表面可具有一平均粗糙度(即十点平均粗糙度(Rz))小于或等于约10微米,例如小于或等于约5微米、或小于或等于约2微米。根据本揭露实施例,该十点平均粗糙度(Rz)的测定方式如下:使用触针式表面粗糙度计(surfcorder ET-3000)依据JIS-B0601:1994的方法量测。
根据本揭露实施例,该积层板可更包含一绝缘基板(未图示),其中该导电层可藉由该膜层配置于该绝缘基板之上。该绝缘基板的材质可为环氧树脂(epoxy resin)、酚醛树脂(phenol formaldehyde resin)、碳氢树脂(hydrocarbon resin)、丙烯酸树脂(acrylicacid resin)、聚酰胺(polyamide)、聚亚酰胺(polyimide)、聚甲基丙烯酸甲酯(polymethylmethacrylate)、聚乙烯四氢咯酮烷酮(polyvinylpyrrolidone)、聚苯乙烯(polystyrene)、聚偏二氟乙烯(polyvinylidene fluoride)、或上述的组合。根据本揭露实施例,该绝缘基板可更包含一补强材料。
根据本揭露实施例,本揭露所述积层板的制备方式可包含以下步骤,首先,提供一树脂组合物。接着,利用一涂布制程将树脂组合物在一导电金属箔上形成一涂层。接着,对该涂层进行一固化制程,以形成一膜层(例如聚酰亚胺膜或聚胺酯-聚酰亚胺)。该固化制程的温度可为约200℃-400℃,以及制程的时间可为30分钟至8小时。此外,在对该涂层进行一固化制程前,可先对该进行一烘烤,以移除树脂组合物的溶剂。根据本揭露实施例,在该固化制程中,该树脂组合物进行酰亚胺化反应(即脱水环化反应)形成一具有聚酰亚胺(或聚胺酯-聚酰亚胺)的固化物。
为了让本揭露的上述和其他目的、特征、和优点能更明显易懂,下文特举数实施例配合所附附图,作详细说明如下:
树脂组合物
实施例1
将二元醇(商品名PripolTM2033,由CRODA制造及贩卖)(10摩尔份)、二异氰酸异佛尔酮(IPDI)(20摩尔份)、以及N-甲基-2-吡咯烷酮(NMP)加入一反应瓶中,得到一溶液(固含量约5wt%)。接着,将上述溶液于140℃反应4小时,得到一具有本揭露所述化合物的溶液。接着,将3,3',4,4'-联苯四甲酸二酐(BPDA)(100摩尔份)加入具有本揭露所述化合物的溶液中。在160℃下搅拌2小时后,于室温下加入间联甲苯胺(m-TB)(90摩尔份)。反应12小时后,得到树脂组合物(1)。
实施例2
将二元醇(商品名PripolTM2033,由CRODA制造及贩卖)(5摩尔份)、二异氰酸异佛尔酮(IPDI)(10摩尔份)、以及N-甲基-2-吡咯烷酮(NMP)加入一反应瓶中,得到一溶液(固含量约5wt%)。接着,将上述溶液于140℃反应4小时,得到一具有本揭露所述化合物的溶液。接着,将3,3',4,4'-联苯四甲酸二酐(BPDA)(100摩尔份)加入具有本揭露所述化合物的溶液中。在160℃下搅拌2小时后,于室温下加入间联甲苯胺(m-TB)(95摩尔份))。反应12小时后,得到树脂组合物(2)。
实施例3
将二元醇(商品名PripolTM2033,由CRODA制造及贩卖)(30摩尔份)、二异氰酸异佛尔酮(IPDI)(60摩尔份)、以及N-甲基-2-吡咯烷酮(NMP)加入一反应瓶中,得到一溶液(固含量约5wt%)。接着,将上述溶液于140℃反应4小时,得到一具有本揭露所述化合物的溶液。接着,将3,3',4,4'-联苯四甲酸二酐(BPDA)(100摩尔份)加入具有本揭露所述化合物的溶液中(BPDA与本揭露所述化合物的摩尔比为约2)。在160℃下搅拌2小时后,于室温下加入联甲苯胺(m-TB)(70摩尔份))。反应12小时后,得到树脂组合物(3)。
实施例4
将二元醇(商品名PripolTM2033,由CRODA制造及贩卖)(75摩尔份)、二异氰酸异佛尔酮(IPDI)(150摩尔份)、以及N-甲基-2-吡咯烷酮(NMP)加入一反应瓶中,得到一溶液(固含量约5wt%)。接着,将上述溶液于140℃反应4小时,得到一具有本揭露所述化合物的溶液。接着,将马来酸酐(MA)(150摩尔份)加入具有本揭露所述化合物的溶液中(马来酸酐与本揭露所述化合物的摩尔比为约2)。在160℃下搅拌2小时后,得到树脂组合物(4)。
比较例1
将二元醇(商品名PripolTM2033,由CRODA制造及贩卖)(40摩尔份)、二异氰酸异佛尔酮(IPDI)(80摩尔份)、以及N-甲基-2-吡咯烷酮(NMP)加入一反应瓶中,得到一溶液(固含量约5wt%)。接着,将上述溶液于140℃反应4小时,得到一具有本揭露所述化合物的溶液。接着,将3,3',4,4'-联苯四甲酸二酐(BPDA)(100摩尔份)加入具有本揭露所述化合物的溶液中。在160℃下搅拌2小时后,于室温下加入间联甲苯胺(m-TB)(60摩尔份))。反应12小时后,得到树脂组合物(5)。
比较例2
将二胺(商品名Priamine 1075,由日本禾大公司制造及贩卖)(10摩尔份)、间联甲苯胺(m-TB)(90摩尔份)、3,3',4,4'-联苯四甲酸二酐(BPDA)(100摩尔份)、以及N-甲基-2-吡咯烷酮(NMP)加入一反应瓶中,得到一溶液(固含量约5wt%)。接着,将上述溶液于160℃下反应12小时,得到树脂组合物(6)。
比较例3
将间联甲苯胺(m-TB)(100摩尔份)、3,3',4,4'-联苯四甲酸二酐(BPDA)(100摩尔份)、以及N-甲基-2-吡咯烷酮(NMP)加入一反应瓶中,得到一溶液(固含量约5wt%)。接着,将上述溶液于160℃下反应12小时,得到树脂组合物(7)。
比较例4
将4,4'-二氨基二苯醚(4,4'-ODA),、对苯基二(偏苯三酸酯)二酸酐(TAHQ)(100摩尔份)、以及N-甲基-2-吡咯烷酮(NMP)加入一反应瓶中,得到一溶液(固含量约5wt%)。接着,将上述溶液于160℃下反应12小时,得到树脂组合物(8)。
制备实施例1-4及比较例1-4所述树脂组合物(1)-(8)的成份如表1所示。
表1
树脂组合物的固化物的性质量测
分别使用刮刀涂布法将所得的树脂组合物(1)-(8)涂布于一铜箔上,形成一涂层(厚度为约18μm)。接着,在100℃下烘烤该涂层30分钟,移除溶剂(NMP)。接着,将包含该涂层的涂铜箔置于氮气环境并于350℃下进行酰亚胺化反应(脱水环化反应)60分钟,得到具有一膜层(包含树脂组合物的固化物)的铜箔。接着,对所得膜层及铜箔进行剥离强度测试,结果如表2所示。剥离强度试验是以万能拉力试验机(SHIMADZU型号AGS-X)依据IPC TM-6502.4.8的规范量测90°撕离强度。
最后,以蚀刻制程将铜箔移除,获得包含树脂组合物的固化物的膜层。
接着,量测由树脂组合物(1)-(8)所制得的膜层其吸湿率以及吸湿前后的介电常数(dielectric coefficient、Dk)及介电损失因子(dielectric loss factor、Df),并评估由树脂组合物(1)-(8)所制得的膜层的耐化性,结果如表2所示。吸湿率的量测方式是以下式所决定:吸湿率=(W1-W0)/W0 x 100%,其中W0为膜层于烘箱中以100℃烘烤1小时后,并冷却至室温后的重量;W0为膜层于23℃下浸渍于水中24小时后的重量。介电常数(dielectric coefficient、Dk)及介电损失因子(dielectric loss factor、Df)是使用微波诱电分析仪(microwave dielectrometer,购自AET公司)于10GHz频率下量测。吸湿后的介电常数及介电损失因子量测是在膜层于23℃下浸渍于水中24小时后进行。耐化性的评估方式为将膜层浸于加热至70℃的甲乙酮(methyl ethyl ketone,MEK)10分钟后,以水冲洗5分钟,观察经此处理的膜层的膜厚及形状是否改变,膜厚及形状无明显改变记录为O,膜厚及形状改变记录为X。
表2
由表1及表2可知,在树脂组合物中(实施例1-4及比较例1),当本揭露所述化合物与二胺的摩尔比在1:19至3:7的范围内时,可在不降低该树脂组合物的固化物的介电常数及介电损失因子以及不增加吸湿率的前提下,改善该树脂组合物的固化物的耐化性。由比较例2可得知,以高碳数的二胺(Priamine 1075)取代本揭露所述化合物,虽然对所得树脂组合物的固化物(膜层)的介电常数及介电损失因子影响不大,但所得膜层与铜箔间的接合强度明显降低,使得该膜层易由铜箔上剥离。由比较例3及4可得知,以二胺(m-TB或4,4'-ODA)取代本揭露所述化合物,除了会增加吸湿率、介电常数及介电损失因子外,且会导致该膜层易由铜箔上剥离。
虽然本揭露已以数个实施例揭露如上,然其并非用以限定本揭露,任何本技术领域中具有通常知识者,在不脱离本揭露的精神和范围内,当可作任意的更动与润饰,因此本揭露的保护范围当视后附的申请专利范围所界定者为准。
Claims (16)
2.如权利要求1所述的化合物,其中A1是直链、分枝、或分枝环状的基团,且化学式为-CnH2n-、-CnH2(n-1)-、-CnH2(n-2)-、-CnH2(n-3)-、-CnH2(n-4)-、-CnH2(n-5)-、或-CnH2(n-6)-,其中n为24至48。
5.一种树脂组合物,包含:
权利要求1-4中任一项所述的化合物;以及
一酸酐,其中该酸酐包含单酸酐、二酸酐、或上述的组合。
6.如权利要求5所述的树脂组合物,当该酸酐是单酸酐时,该酸酐具有摩尔数M1、而该化合物具有摩尔数M2,其中1.5≤M2/M1≤2.5。
7.如权利要求5所述的树脂组合物,当该酸酐是二酸酐时,该酸酐具有摩尔数M1、而该化合物具有摩尔数M2,其中0.05≤M2/M1≤1。
8.如权利要求5所述的树脂组合物,当该酸酐是单酸酐及二酸酐的组合时,该酸酐具有摩尔数M1、而该化合物具有摩尔数M2,其中0.05≤M2/M1≤3,且该单酸酐及该二酸酐的摩尔比是1:99至99:1。
9.如权利要求5所述的树脂组合物,其中该单酸酐是马来酸酐、琥珀酸酐、苯乙烯马来酸酐、5-原冰片烯-2,3-二羧酸酐、3,6-环氧-1,2,3,6-四氢酞酸酐、3,4,5,6-四氢邻苯二甲酐、邻苯二甲酐、1,2,3,6-四氢邻苯二甲酐、衣康酸酐、柠康酸酐、或2,3-二甲基马来酸酐。
11.如权利要求5所述的树脂组合物,其中该二酸酐是苯均四酸二酐、4,4'-六氟异亚丙基二苯二甲酸二酐、4,4'-氧二醚酸酐、3,3',4,4'-联苯四甲酸二酐、4,4'-双酚A二酐、对苯基二(偏苯三酸酯)二酸酐、对苯二酚二酞酸酐、或上述的组合。
12.如权利要求5所述的树脂组合物,当该酸酐是二酸酐、或该酸酐是单酸酐及二酸酐的组合时,该树脂组合物更包含:
一二胺化合物,其中该酸酐具有摩尔数M1、该化合物具有摩尔数M2、以及该二胺化合物具有摩尔数M3,其中0.5≤(M2+M3)/M1≤3,且0.1≤M2/(M2+M3)≤0.3。
14.如权利要求12所述的树脂组合物,其中该二胺化合物是联甲苯胺、间二氨基苯,对二氨基苯、4,4'-二氨基二苯醚,3,4'-二氨基二苯醚、1,4-双(4-氨苯氧基)苯、1,3-双(4-氨苯氧基)苯、1,2-双(4-氨苯氧基)苯、1,3-双(3-氨苯氧基)苯、2,5-双(4-氨苯氧基)甲苯)、双(4-[4-氨基苯氧基]苯)醚、4,4'-二(4-氨基苯氧基)联苯、2,2'-双[4-(4-氨基苯氧基苯基)]丙烷、4,4'-双(4-氨基苯氧基)苯砜、2,2'-双(三氟甲基)-4,4'-二氨基联苯、1,4-苯二胺、或上述的混合。
15.一种积层板,包含:
导电层,具有一表面;以及
膜层,配置于该导电层的表面,其中该膜层包含权利要求5所述的树脂组合物的固化物。
16.如权利要求15所述的积层板,其中该导电层是铜箔、镍箔或铝箔。
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US20150159043A1 (en) * | 2013-12-05 | 2015-06-11 | Taimide Technology Incorporation | Multilayered polyimide film having a low dielectric constant, laminate structure including the same and manufacture thereof |
US20170009017A1 (en) * | 2015-07-07 | 2017-01-12 | Microcosm Technology CO, LTD. | Polymide resin, thin film thereof and method for manufacturing the same |
US20170210854A1 (en) * | 2016-01-27 | 2017-07-27 | Arisawa Mfg. Co., Ltd. | Polyimide resin precursor |
WO2020158360A1 (ja) * | 2019-01-29 | 2020-08-06 | 東洋紡株式会社 | ダイマージオール共重合ポリイミドウレタン樹脂を含む接着剤組成物 |
TW202037628A (zh) * | 2019-01-29 | 2020-10-16 | 日商東洋紡股份有限公司 | 含有二聚物二醇共聚聚醯亞胺胺甲酸酯樹脂之黏接劑組成物 |
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TW202225238A (zh) | 2022-07-01 |
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