TW201601912A - 低介電複合材料及其積層板和電路板 - Google Patents
低介電複合材料及其積層板和電路板 Download PDFInfo
- Publication number
- TW201601912A TW201601912A TW103145874A TW103145874A TW201601912A TW 201601912 A TW201601912 A TW 201601912A TW 103145874 A TW103145874 A TW 103145874A TW 103145874 A TW103145874 A TW 103145874A TW 201601912 A TW201601912 A TW 201601912A
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- Prior art keywords
- low dielectric
- resin
- flame retardant
- composite material
- phosphorus
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- 239000002131 composite material Substances 0.000 title claims abstract description 42
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 61
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 61
- 239000011574 phosphorus Substances 0.000 claims abstract description 61
- 239000003063 flame retardant Substances 0.000 claims abstract description 57
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000011342 resin composition Substances 0.000 claims abstract description 45
- -1 vinyl compound Chemical class 0.000 claims abstract description 41
- 239000000758 substrate Substances 0.000 claims abstract description 29
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 16
- 229920005989 resin Polymers 0.000 claims description 66
- 239000011347 resin Substances 0.000 claims description 66
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 40
- 239000011889 copper foil Substances 0.000 claims description 33
- 229920001955 polyphenylene ether Polymers 0.000 claims description 23
- 229920001577 copolymer Polymers 0.000 claims description 22
- 239000002966 varnish Substances 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 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 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 239000005011 phenolic resin Substances 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000004744 fabric Substances 0.000 claims description 5
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 5
- 229920002799 BoPET Polymers 0.000 claims description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002657 fibrous material Substances 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 4
- 238000005470 impregnation Methods 0.000 claims description 4
- 239000004745 nonwoven fabric Substances 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 239000002759 woven fabric Substances 0.000 claims description 3
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 claims description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- 239000004713 Cyclic olefin copolymer Substances 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- AFTLIIOXEHXDOZ-UHFFFAOYSA-N buta-1,3-diene;furan-2,5-dione;styrene Chemical compound C=CC=C.O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 AFTLIIOXEHXDOZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- NAKOELLGRBLZOF-UHFFFAOYSA-N phenoxybenzene;pyrrole-2,5-dione Chemical compound O=C1NC(=O)C=C1.O=C1NC(=O)C=C1.C=1C=CC=CC=1OC1=CC=CC=C1 NAKOELLGRBLZOF-UHFFFAOYSA-N 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- XDOBJOBITOLMFI-UHFFFAOYSA-N pyrrole-2,5-dione;toluene Chemical compound CC1=CC=CC=C1.O=C1NC(=O)C=C1 XDOBJOBITOLMFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 claims 1
- AWLBBUKQZALJGW-UHFFFAOYSA-N 3-[(2,3-dimethylphenyl)methyl]pyrrole-2,5-dione Chemical compound CC1=C(CC=2C(=O)NC(C=2)=O)C=CC=C1C AWLBBUKQZALJGW-UHFFFAOYSA-N 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 238000009941 weaving Methods 0.000 claims 1
- 230000009477 glass transition Effects 0.000 abstract description 10
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 abstract description 6
- 125000000524 functional group Chemical group 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 238000001212 derivatisation Methods 0.000 abstract description 2
- IFOOABKNGLKLLE-UHFFFAOYSA-N OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.O Chemical compound OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.O IFOOABKNGLKLLE-UHFFFAOYSA-N 0.000 abstract 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 8
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 239000011888 foil Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
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- 238000000034 method Methods 0.000 description 5
- 229920001568 phenolic resin Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 4
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- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910000420 cerium oxide Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QMAQLCVJIYANPZ-UHFFFAOYSA-N 2-propoxyethyl acetate Chemical compound CCCOCCOC(C)=O QMAQLCVJIYANPZ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- VWBYXJRDIQCSLW-UHFFFAOYSA-N O=[P](c1ccccc1)c1ccccc1 Chemical compound O=[P](c1ccccc1)c1ccccc1 VWBYXJRDIQCSLW-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 239000000654 additive Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
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- 238000011056 performance test Methods 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
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- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- BSKJUAKMZZKMKC-UHFFFAOYSA-N 1,2-ditert-butyl-3,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)(C)C)C(C(C)(C)C)=C1C(C)C BSKJUAKMZZKMKC-UHFFFAOYSA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- XBHHVVHQVJQMSL-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1.O=C1C=CC(=O)N1C1=CC=CC=C1 XBHHVVHQVJQMSL-UHFFFAOYSA-N 0.000 description 1
- UGHIQYNKFXEQPU-UHFFFAOYSA-N 2,3-dichloro-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(Cl)=C1Cl UGHIQYNKFXEQPU-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
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- VRRCYIFZBSJBAT-UHFFFAOYSA-N 4-methoxybutanoic acid Chemical compound COCCCC(O)=O VRRCYIFZBSJBAT-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- ACOVOCNAWKNTCV-UHFFFAOYSA-N C1(=C(C(=CC=C1)C)C)N1C(C=CC1=O)=O.CC1=C(CC=2C(=O)NC(C2)=O)C=CC=C1C Chemical compound C1(=C(C(=CC=C1)C)C)N1C(C=CC1=O)=O.CC1=C(CC=2C(=O)NC(C2)=O)C=CC=C1C ACOVOCNAWKNTCV-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- CAVCGVPGBKGDTG-UHFFFAOYSA-N alumanylidynemethyl(alumanylidynemethylalumanylidenemethylidene)alumane Chemical compound [Al]#C[Al]=C=[Al]C#[Al] CAVCGVPGBKGDTG-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 229910000679 solder Inorganic materials 0.000 description 1
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- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910003468 tantalcarbide Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
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- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
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- C08K5/5397—Phosphine oxides
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- C08K5/5406—Silicon-containing compounds containing elements other than oxygen or nitrogen
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- C—CHEMISTRY; METALLURGY
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- B32B2307/306—Resistant to heat
- B32B2307/3065—Flame resistant or retardant, fire resistant or retardant
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- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C09D171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C09D171/12—Polyphenylene oxides
-
- 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
- H05K1/0213—Electrical arrangements not otherwise provided for
- H05K1/0237—High frequency adaptations
- H05K1/024—Dielectric details, e.g. changing the dielectric material around a transmission line
-
- 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
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
-
- 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
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- H05K2201/012—Flame-retardant; Preventing of inflammation
-
- 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
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- H05K2201/0195—Dielectric or adhesive layers comprising a plurality of layers, e.g. in a multilayer structure
-
- 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
- H05K3/46—Manufacturing multilayer circuits
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Abstract
本發明公開了一種低介電複合材料及由其製得的積層板及電路板。該複合材料係將含磷阻燃劑之低介電樹脂組合物附著在基材上而製得；該組合物包含：（A）含磷阻燃劑；（B）乙烯基化合物。該含磷阻燃劑具有如式（一）所示結構。□本發明藉由對二苯基磷氧進行衍生化，製得的含磷阻燃劑不具有反應官能團，搭配乙烯基化合物得到的樹脂組合物可製備具有較低熱膨脹率、較高耐熱性、較高玻璃轉化溫度及較低介電常數和介電損耗的複合材料，並可製造具有高玻璃轉化溫度、低介電特性、無鹵阻燃性以及低基板熱膨脹係數等特性的積層板及電路板。
Description
本發明係關於樹脂複合材料，尤指一種低介電複合材料及由其製得的積層板和電路板。
低介電樹脂材料為現今高傳輸速率的基板開發主要方向，其中，低介電損耗及低介電常數為低介電樹脂材料的主要評價指標，然而現有的低介電樹脂材料大多使用含鹵阻燃劑而不環保，使用一般含磷阻燃劑則造成阻燃性不佳、基板耐熱性不佳和基板熱膨脹率較大等缺點。
為了克服上述習知技術使用含鹵阻燃劑不環保的缺點與現有含磷阻燃劑阻燃性能不佳的不足，本發明之首要目的在於提供一種低介電複合材料。該複合材料具有高玻璃轉化溫度、低介電性、無鹵阻燃性以及低基板熱膨脹率等特性。 本發明另一目的在於提供一種上述低介電複合材料的製備方法。 本發明再一目的在於提供基於上述低介電複合材料製備得到的積層板和電路板。 本發明之目的可藉由下述方案實現： 一種低介電複合材料，係將含磷阻燃劑之低介電樹脂組合物附著在基材上而製得。 所述含磷阻燃劑之低介電樹脂組合物，包含以下組分： （A）含磷阻燃劑；以及 （B）乙烯基化合物。 本發明所述之含磷阻燃劑具有如式（一）所示結構：（一） 其中，A為共價鍵、C6
～C12
伸芳基、C3
～C12
伸環烷基、C6
～C12
伸環烯基、亞甲基或C2
～C12
伸烷基； R1
和R2
相同或者不同，且分別為H、烷氧基、芳氧基、烷基、芳基或者矽烷基； R3
和R4
相同或者不同，且分別為H、羥基、C1
～C6
烷基，或R3
和R4
只存在一者且與碳原子形成羰基； 每個n獨立為0～6的整數，當A為C6
～C12
伸芳基或者共價鍵時，n不為0。 其中，上述基材沒有特別限定，所有可達成支撐和增強作用的材料均可。該基材較佳為纖維材料、織布、不織布、PET膜（polyester film）、PI膜（polyimide film）、銅箔（copper）和背膠銅箔（resin coated copper，RCC）中的一種，如玻璃纖維布等，其可增加複合材料的機械強度。此外，在不影響本發明低介電複合材料性能的前提下，該基材可選擇性經由矽烷偶合劑進行預處理。該複合材料具有高玻璃轉化溫度、低介電性、無鹵阻燃性以及低基板熱膨脹率等特性。 本發明所述之含磷阻燃劑較佳具有如下式（二）～（十五）所示結構的其中一種： （二） （三） （四） （五） （六） （七） （八） （九） （十） （十一） （十二） （十三）（十四） （十五） 其中，TMS為三甲基矽烷基。 本發明的含磷阻燃劑熔點高，大於300℃。 所述乙烯基化合物可為乙烯基聚苯醚樹脂、乙烯苄基化合物樹脂、聚烯烴化合物和馬來醯亞胺樹脂中的至少一種。 所述乙烯苄基化合物樹脂為含乙烯苄基結構的聚合物或者預聚體，如晉一化工的DP-85T（乙烯苄基醚化-雙環戊二烯-苯酚樹脂）。 所述乙烯基聚苯醚樹脂指封端基團具有不飽和雙鍵的聚苯醚樹脂。 於較佳實施例中，所述乙烯基聚苯醚樹脂指具有以下式（十六）和式（十七）結構之一的聚苯醚樹脂，但不限於以下結構：（十六）（十七） 其中，-(O-X-O)- 指或； -(Y-O)-指； R5
、R6
為氫原子，R7
、R8
、R9
、R10
和R11
相同或不同，且為氫原子、鹵素原子、烷基或者鹵烷基； R12
、R13
、R18
和 R19
相同或者不同，且為鹵素原子、C1
～C6
烷基或者苯基；R14
、R15
、R16
和R17
相同或者不同，且為氫原子、鹵素原子、C1
～C6
烷基或者苯基； R20
、R21
、R22
、R23
、R24
、R25
、R26
和R27
相同或者不同，且為鹵素原子、C1
～C6
烷基、苯基或者氫原子；A為C1
～C20
的線型、支鏈或者伸環狀烴，較佳為-CH2
-或 -C(CH3
)2
-； R28
和R29
相同或者不同，且為鹵素原子、C1
～C6
烷基或者苯基；R30
和R31
相同或者不同，且為氫原子、鹵素原子、C1
～C6
烷基或者苯基； Z代表具有至少一個碳原子的有機基團，該基團可以包含氧原子、氮原子、硫原子和/或鹵素原子，如Z可為亞甲基（-CH2
-）； a和b分別為1～30的自然數； 其中，G為雙酚A、雙酚F或共價鍵；m和n分別為1～15的自然數。
所述乙烯苄基醚聚苯醚樹脂指含有 結構的聚苯醚樹脂。 於較佳實施例中，所述乙烯基聚苯醚樹脂指甲基丙烯酸聚苯醚樹脂（如Sabic的產品SA-9000）、乙烯苄基醚聚苯醚樹脂（如三菱瓦斯化學的產品OPE-2st）和改性的乙烯基聚苯醚樹脂（如晉一化工的PPE/VBE 7205L）中的至少一種。 本發明所述的乙烯基聚苯醚樹脂，相較於雙官能末端羥基的聚苯醚樹脂，具有較低的介電特性，即具有較低的介電常數和介電損耗。 所述聚烯烴化合物可為苯乙烯-丁二烯-二乙烯基苯共聚物、氫化苯乙烯-丁二烯-二乙烯基苯共聚物、苯乙烯-丁二烯-馬來酸酐共聚物、聚丁二烯-尿酯-甲基丙烯酸甲酯共聚物、苯乙烯-丁二烯共聚物、聚丁二烯均聚物、苯乙烯-異戊二烯-苯乙烯共聚物、苯乙烯-丁二烯-二乙烯基苯共聚物、馬來酸酐化苯乙烯-丁二烯共聚物、甲基苯乙烯共聚物、石油樹脂和環型烯烴共聚物中的至少一種。 所述馬來醯亞胺樹脂並無特別限制，所有已知使用的馬來醯亞胺樹脂均可，該馬來醯亞胺樹脂較佳為下列物質中的至少一種：4,4’-雙馬來醯亞胺二苯甲烷、苯甲烷馬來醯亞胺寡聚物、N,N’-間亞苯基雙馬來醯亞胺、雙酚A二苯基醚雙馬來醯亞胺、3,3’-二甲基-5,5’-二乙基-4,4’-二苯基甲烷雙馬來醯亞胺、N,N’-(4-甲基-1,3-亞苯基)雙馬來醯亞胺、1,6-雙馬來醯亞胺-(2,2,4-三甲基)己烷、2,3-二甲基苯馬來醯亞胺（N-2,3-Xylylmaleimide）、2,6-二甲基苯馬來醯亞胺（N-2,6-Xylenemaleimide）、N -苯基馬來醯亞胺（N-phenylmaleimide）和上述化合物的預聚體，例如二烯丙基化合物與馬來醯亞胺化合物的預聚物。 本發明的含磷阻燃劑之低介電樹脂組合物係由含磷阻燃劑和乙烯基化合物混合而得。 本發明的含磷阻燃劑之低介電樹脂組合物中磷含量可藉由改變所述含磷阻燃劑的用量進行調整；其中，當本發明的低介電樹脂組合物的磷含量達到2 wt%，即可達到有效的阻燃功效，較佳為2～3.5 wt%。 本發明的含磷阻燃劑之低介電樹脂組合物兼具高玻璃轉化溫度、低介電常數、低介電損耗、無鹵阻燃性以及製備得到的基板具有低基板熱膨脹率等良好特性。 為了達到上述目的，本發明的含磷阻燃劑之低介電樹脂組合物較佳包含以下組分：（A）含磷阻燃劑；（B）乙烯基化聚苯醚樹脂；（C）苯乙烯-丁二烯-二乙烯基苯共聚物、苯乙烯-丁二烯-馬來酸酐共聚物和聚丁二烯-尿酯-甲基丙烯酸甲酯共聚物中的至少一種；（D）馬來醯亞胺樹脂。 更佳係包含以下重量份計的組分：（A）10～90份的含磷阻燃劑；（B）100份的乙烯基化聚苯醚樹脂；（C）10～90份的苯乙烯-丁二烯-二乙烯基苯共聚物、苯乙烯-丁二烯-馬來酸酐共聚物和聚丁二烯-尿酯-甲基丙烯酸甲酯共聚物中的至少一種；（D）10～90份的馬來醯亞胺樹脂。 在不影響本發明的含磷阻燃劑之低介電樹脂組合物效果的前提下，可進一步包含以下添加物中的至少一種：硬化促進劑、溶劑、交聯劑、矽烷偶合劑、無機填充物。 在不影響本發明的含磷阻燃劑之低介電樹脂組合物的效果之前提下，可選擇性添加一種或一種以上的硬化促進劑以促進樹脂的固化速率。任一種可增加本發明的含磷阻燃劑之低介電樹脂組合物固化速率的硬化促進劑均可使用。較佳的硬化促進劑包含可產生自由基的過氧化物硬化促進劑，包括但不限於：過氧化二異丙苯、過氧苯甲酸叔丁酯及二叔丁基過氧化二異丙基苯，更佳為二叔丁基過氧化二異丙基苯。 所述矽烷偶合劑可為矽烷化合物及矽氧烷化合物中的至少一種。 於較佳實施例中，所述矽烷偶合劑為胺基矽烷化合物、胺基矽氧烷化合物、苯乙烯基矽烷化合物、苯乙烯基矽氧烷化合物、壓克力矽烷化合物、壓克力矽氧烷化合物、甲基壓克力矽烷化合物、甲基壓克力矽氧烷化合物、烷基矽烷化合物和烷基矽氧烷化合物中的至少一種。 所述溶劑可為甲醇、乙醇、乙二醇單甲醚、丙酮、丁酮、甲基異丁基酮、環己酮、甲苯、二甲苯、甲氧基乙基乙酸酯、乙氧基乙基乙酸酯、丙氧基乙基乙酸酯、乙酸乙酯、二甲基甲醯胺、丙二醇甲基醚、γ-丁內酯（gamma-Butyrolactone，GBL）和雙異丁基酮（Diisobutyl Ketone，DIBK）中的至少一種。 添加無機填充物的主要作用，在於增加樹脂組合物的熱傳導性、改善其熱膨脹性及機械強度等特性，且無機填充物較佳係均勻分佈於該樹脂組合物中。 於較佳實施例中，無機填充物可包含二氧化矽（球型、熔融態、非熔融態、多孔質或中空型）、氧化鋁、氫氧化鋁、氧化鎂、氫氧化鎂、碳酸鈣、氮化鋁、氮化硼、碳化鋁矽、碳化矽、碳酸鈉、二氧化鈦、氧化鋅、氧化鋯、石英、鑽石粉、類鑽石粉、石墨、碳酸鎂、鈦酸鉀、陶瓷纖維、雲母、勃姆石、鉬酸鋅、鉬酸銨、硼酸鋅、磷酸鈣、煆燒滑石、滑石、氮化矽、莫來石、煆燒高嶺土、黏土、鹼式硫酸鎂晶鬚、莫來石晶鬚、硫酸鋇、氫氧化鎂晶鬚、氧化鎂晶鬚、氧化鈣晶鬚、奈米碳管、奈米級二氧化矽與其相關無機粉體、和具有有機核外層殼為絕緣體修飾的粉體粒子中的至少一種，且無機填充物可為球型、纖維狀、板狀、粒狀、片狀或針鬚狀。 本發明的低介電複合材料的製備方法，具體包括以下步驟： 將含磷阻燃劑之低介電樹脂組合物溶於溶劑，製成樹脂清漆（varnish），以含浸或塗覆等方式附著於基材上，並經由高溫加熱形成半固化態，得到低介電複合材料。 上述複合材料經由高溫加熱或高溫且高壓下加熱可固化形成固化膠片或是固態絕緣層，其中樹脂組合物若含有溶劑，則該溶劑會於高溫加熱過程中揮發移除。 上述製備方法中，所述的溶劑可為甲醇、乙醇、乙二醇單甲醚、丙酮、丁酮、甲基異丁基酮、環己酮、甲苯、二甲苯、甲氧基乙基乙酸酯、乙氧基乙基乙酸酯、丙氧基乙基乙酸酯、乙酸乙酯、二甲基甲醯胺、丙二醇甲基醚、γ丁內酯和雙異丁基酮中的至少一種。 於上述製備方法中，所述樹脂清漆的濃度可根據生產工藝需要進行任意調整，較佳為45～70 wt%。所述高溫加熱係指進行加熱使溶劑揮發即可，溫度可根據溶劑種類進行任意調整，優選為100～170℃。本發明的低介電複合材料厚度沒有特別限制，可根據實際需要進行調整，但較佳為30～75 μm，更佳為38～50 μm。 本發明所述低介電複合材料可根據使用的基材不同而得到不同的產物，如半固化片、樹脂膜、背膠銅箔、撓性背膠銅箔等。 將含磷阻燃劑之低介電樹脂組合物的樹脂清漆，含浸在纖維材料、織布或不織布上，並經由高溫加熱形成半固化態，得到半固化片。 或者將含磷阻燃劑之低介電樹脂組合物的樹脂清漆，塗覆於PET膜或PI膜上，並經由高溫加熱形成半固化態，得到樹脂膜。 或者將含磷阻燃劑之低介電樹脂組合物的樹脂清漆，塗覆於銅箔或覆PI膜銅箔的PI膜上，並經由高溫加熱形成半固化態，得到背膠銅箔；上述塗覆於覆PI膜銅箔的PI膜上得到的背膠銅箔亦稱撓性背膠銅箔。 換言之，將含磷阻燃劑之低介電樹脂組合物的樹脂清漆，塗覆於覆PI膜銅箔的PI膜上，並經由高溫加熱，得到撓性背膠銅箔。 一種積層板（laminate）可基於上述低介電複合材料製得。所述積層板係藉由將上述本發明低介電複合材料與金屬箔疊置壓合得到。所述金屬箔可為本領域任意常用金屬箔，如銅箔。製備得到的銅箔基板（copper clad laminate，或稱覆銅板或覆銅箔基板），具有高玻璃轉化溫度、低介電特性、無鹵阻燃性以及低基板熱膨脹率等特性，且特別適用於高速度高頻率訊號傳輸電路板。所述積層板包含兩層或兩層以上金屬箔及置於金屬箔之間的至少一層複合材料。其中，金屬箔，例如為銅箔，可進一步包含鋁、鎳、鉑、銀、金等至少一種金屬合金；將前述複合材料疊合於兩層金屬箔間於高溫與高壓下進行壓合而成。 所述壓合工藝條件為本領域常用壓合工藝條件即可。 一種電路板，係基於上述積層板製得。 將上述積層板進一步經過製作線路等製作加工後，可得到電路板。該電路板與電子元件接合後可於高溫、高濕度等嚴苛環境下操作而並不影響其品質。上述本發明製備得到的印刷電路板，具有高玻璃轉化溫度、低介電特性、無鹵阻燃性以及低基板熱膨脹率等特性，且適用於高速度高頻率訊號傳輸。其中，該電路板包含至少一個前述積層板，且該電路板可由現有已知工藝製作而成。 本發明的機制大致如下： 本發明藉由對二苯基磷氧進行衍生化，製備得到的含磷阻燃劑不具有反應官能團，相較於一般的含磷樹脂具有更好的介電特性；一般的含磷樹脂由於具有極性基團造成介電性過高，如本領域現廣泛使用的含磷酚醛樹脂，DOPO-雙酚A酚醛樹脂（DOPO-BPAN）（陶氏化學的XZ92741），其具有羥基，羥基即為極性官能團，會造成介電性過高；且本發明的含磷阻燃劑熔點高（大於300℃），遠高於業界目前廣泛使用的低熔點非反應性含磷阻燃劑，例如磷腈化合物（大塚化學的SPB-100，熔點約110℃）以及磷酸酯化合物（大八化學的PX-200，熔點約105℃），本發明搭配使用乙烯基化合物可製備得到具有較低熱膨脹率、較高耐熱性、較高玻璃轉化溫度及較低介電常數和介電損耗的半固化片、樹脂膜、積層板及電路板。 本發明相對於習知技術，具有如下的優點及有益效果： （1）本發明的含磷阻燃劑之低介電樹脂組合物組分中含磷阻燃劑不含有反應官能團，不參與反應，具有更好的介電特性。 （2）本發明的含磷阻燃劑熔點高（大於300℃），搭配使用乙烯基化合物可製備得到具有較低熱膨脹率、較高耐熱性、較高玻璃轉化溫度及較低介電常數和介電損耗的半固化片、樹脂膜、積層板及電路板。 （3）本發明的含磷阻燃劑之低介電樹脂組合物在不使用鹵素阻燃劑的前提下，可有效達到UL94 V-0的阻燃功效。
以下結合實施例和附圖對本發明作進一步詳細的描述，但本發明的實施方式不限於此。 下列實施例中使用的化學品名如下： DPPO：二苯基磷氧，購自詠友企業股份有限公司。 SA-9000：末端甲基聚丙烯酸酯的雙酚A聚苯醚樹脂，購自Sabic公司。 OPE-2st：末端乙烯苄基醚的聯苯聚苯醚樹脂，購自三菱瓦斯化學。 Ricon184Ma6：苯乙烯-丁二烯-馬來酸酐共聚物，購自Cray Valley公司。 Ricon257：苯乙烯-丁二烯-二乙烯基苯共聚物，購自Cray Valley公司。 Homide108：苯甲烷馬來醯亞胺，購自HOS-Technik公司。 SPB-100：磷腈化合物，購自大塚化學。 PX-200：間苯二酚雙 [二(2,6-二甲基苯基)磷酸酯]，購自大八化學。 XZ92741：DOPO-雙酚A酚醛樹脂，購自陶氏化學。 DCP：過氧化二異丙苯，購自詠友企業股份有限公司。 R-45vt：聚丁二烯-尿酯-甲基丙烯酸甲酯，購自Cray Valley。 SQ-5500：經烷基矽氧烷化合物處理的球型態二氧化矽，購自Admatechs。 DP-85T：乙烯苄基醚化-雙環戊二烯-苯酚樹脂，購自晉一化工。 PPE/VBE 7205L：改性的乙烯基聚苯醚樹脂，購自晉一化工。 實施例1：結構式（三）含磷阻燃劑的製備 將206克的DPPO（Diphenylphosphine Oxide，二苯基磷氧）、90克的二氯-對二甲苯和1200克1,2-二氯苯攪拌混合，在氮氣氛圍中160℃下加熱反應12～24 hr，冷卻至室溫並過濾，真空乾燥，得到結構式（三）所示化合物A，為白色粉末，其中化合物A中磷含量約為12 %。 分析：TGA測試Td值為：379℃（5%裂解時，結果見圖1）；DSC測得熔點溫度為334℃（結果見圖2），而現有使用的磷腈化合物（SPB-100）的熔點為110℃，縮合磷酸酯（PX-200）的熔點為105℃，含磷酚醛樹脂，例如DOPO-雙酚A酚醛樹脂，其常溫下為液態樹脂。由此可見，本發明製備得到的含磷阻燃劑具有較高的熔點。 對反應前的DPPO和化合物A進行紅外光掃描，峰值分析見表1～2和圖3～4，由圖可見，反應前DPPO的P-H官能基於FTIR上的波峰2300 cm-1
～2354 cm-1
在合成後的化合物A紅外圖譜中消失，證明成功製備得到目標產物結構式（三）所示化合物A。（三）
實施例2：含磷阻燃劑之低介電樹脂組合物的製備 按照表3～8列出的配方將相關成分充分混合，得到樹脂組合物的樹脂清漆，其中E表示本發明的含磷阻燃劑之低介電樹脂組合物實施例，C表示對比實施例。
實施例3：低介電複合材料的製備 將上述E1～E16及C1～C17製備得到的樹脂組合物的樹脂清漆分別塗布於PET膜上（或PI膜），使樹脂組合物（厚度約30 μm）均勻附著於膜上，加熱烘烤成半固化態以得到樹脂膜。其中，E1～E16及C3、C4的烘烤條件為：160℃烘烤4分鐘；C1、C2和C5～C17的烘烤條件為：120℃烘烤4分鐘。 實施例4：低介電複合材料的製備 將上述E1～E16及C1～C17製備得到的樹脂組合物的樹脂清漆分別塗布於銅箔上，使樹脂組合物（厚度約30μm）均勻附著，加熱烘烤成半固化態，得到背膠銅箔。其中，E1～E16及C3、C4的烘烤條件為：160℃烘烤4分鐘；C1、C2和C5～C17的烘烤條件為：120℃烘烤4分鐘。 實施例5：低介電複合材料的製備 將上述E1～E16及C1～C17製備得到的樹脂組合物的樹脂清漆分別塗布於覆背膠銅箔的膠面PI膜上，以得到銅箔、PI膜、樹脂組合物的結構，使樹脂組合物（厚度約30 μm）均勻附著，加熱烘烤成半固化態，得到撓性背膠銅箔。其中，E1～E16及C3、C4的烘烤條件為：160℃烘烤4分鐘；C1、C2和C5～C17的烘烤條件為：120℃烘烤4分鐘。其中，PI膜可為TPI（熱塑性聚醯亞胺）、PI（聚醯亞胺）中的至少一種。 實施例6：低介電複合材料的製備 將上述E1～E16和C1～C17樹脂組合物的樹脂清漆分別置入一含浸槽中，再將玻璃纖維布（2116玻璃纖維布，購自南亞塑膠工業）通過上述含浸槽，使樹脂組合物附著於玻璃纖維布，再進行加熱烘烤成半固化態而得半固化片。 將上述分別製得的半固化片，取每一種半固化片四張及兩張18 μm銅箔，依銅箔、四片半固化片、銅箔的順序進行疊合，再於真空條件下經由210℃壓合2小時形成銅箔基板，其中四片半固化片固化形成兩銅箔間的絕緣層。 分別將上述含銅箔基板及銅箔蝕刻後不含銅箔的基板做物性測定，其中包括不含銅箔的四片半固化片壓合後的基板，其樹脂含量約為55%，除了介電常數及介電損耗以兩片半固化片不含銅箔基板測定外，其餘不含銅箔基板物性皆為四片半固化片基板所測定，物性測定項目包含玻璃轉化溫度（Tg，DMA儀器量測）、熱膨脹率（CTE z-axis，尺寸漲縮率dimension change：50～260℃，TMA儀器量測，%，尺寸漲縮率越低越好）、含銅基板浸錫測試（solder dip，S/D，288℃，10秒，測耐熱回數）、介電常數（dielectric constant，Dk，AET微波誘電分析儀量測，Dk值越低介電特性越佳）、介電損耗（dissipation factor，Df，AET微波誘電分析儀量測，Df值越低介電特性越佳）、耐燃性（flaming test，UL94，其中等級排列V-0較V-1佳）。 其中E1～E2和C1～C6的樹脂組合物製作的複合材料性能測試結果列於表9中，E3～E16和C7～C17的樹脂組合物製作的複合材料性能測試結果列於表10～12中。綜合比較實施例及比較例可發現，使用化合物A相較於一般含磷添加劑，結果顯示本發明複合材料的Dk、Df值較低，熱膨脹率（z-軸的尺寸漲縮率）亦較低。
結果分析： 由上述表格資料可見，本發明的E1和E2，相對於C1～C6，明顯具有較小的尺寸漲縮率，製備得到的基板熱膨脹率小。同時，本發明的低介電複合材料具有優異的耐熱性。由E1和E2與C1～C3的對比可知，本發明的低介電樹脂組合物由於含有特定的含磷阻燃劑，具有良好的阻燃性，可有效達到UL94 V-0的阻燃功效。 由E4～E7與C8～C12的資料對比可知，本發明的低介電複合材料由於添加了苯乙烯聚合物，進一步降低了介電損耗，得到更佳的介電性，使系統達到較佳的介電性（越低越佳）。 將本發明E13和E14的資料與C7相比較可見，本發明的含磷阻燃劑之低介電樹脂組合物在該配方組合下熱穩定性最好，且熱膨脹率小，介電性佳，為最佳配方。 如上所述，本發明的含磷阻燃劑之低介電樹脂組合物，其藉著包含特定的組成份及比例，可達到低熱膨脹率、低介電常數、低介電損耗、高耐熱性及高耐燃性，其可製作成半固化片或樹脂膜，進而達到可應用於銅箔基板及印刷電路板的目的；就產業上的可利用性而言，利用本發明所衍生的產品，可充分滿足目前市場的需求。 上述實施例為本發明較佳的實施方式，但本發明的實施方式並不受上述實施例的限制，其他的任何未背離本發明的精神實質與原理下所作的改變、修飾、替代、組合、簡化，均應為均等的置換方式，且都包含在本發明的保護範圍之內。
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圖1為實施例1製備得到的含磷阻燃劑之TGA熱重損失分析圖。 圖2為實施例1製備得到的含磷阻燃劑之DSC熔點分析圖。 圖3為DPPO之FTIR光譜圖。 圖4為實施例1製備得到的含磷阻燃劑之FTIR光譜圖。
Claims (11)
- 一種低介電複合材料，其係將含磷阻燃劑之低介電樹脂組合物附著在基材上而得，其中該含磷阻燃劑之低介電樹脂組合物包含以下組分： （A）含磷阻燃劑；以及 （B）乙烯基化合物； 其中，該含磷阻燃劑具有如式（一）所示結構：（一） 其中，A為共價鍵、C6 ～C12 伸芳基、C3 ～C12 伸環烷基、C6 ～ C12 伸環烯基、亞甲基或C2 ～C12 伸烷基； R1 和R2 相同或者不同，且分別為H、烷氧基、芳氧基、烷基、芳基或者矽烷基； R3 和R4 相同或者不同，且分別為H、羥基、C1 ～C6 烷基，或R3 和R4 只存在一者且與碳原子形成羰基； 每個n獨立為0～6的整數，當A為C6 ～C12 伸芳基或者共價鍵時，n不為0。
- 如請求項1所述的低介電複合材料，其中該基材為纖維材料、織布、不織布、PET膜、PI膜、銅箔和背膠銅箔中的一種。
- 如請求項1所述的低介電複合材料，其中所述含磷阻燃劑具有如下式（二）～（十五）所示結構的其中一種： （二） （三） （四） （五） （六） （七） （八） （九） （十） （十一） （十二） （十三）（十四） （十五） 其中，TMS為三甲基矽烷基。
- 如請求項1所述的低介電複合材料，其中，所述乙烯基化合物為乙烯基聚苯醚樹脂、乙烯苄基化合物樹脂、聚烯烴化合物和馬來醯亞胺樹脂中的至少一種。
- 如請求項4所述的低介電複合材料，其中，所述乙烯基聚苯醚樹脂為具有以下式（十六）和式（十七）結構之一的聚苯醚樹脂：（十六）（十七） 其中，-(O-X-O)- 指或； -(Y-O)-指； R5 、R6 為氫原子，R7 、R8 、R9 、R10 和R11 相同或不同且為氫原子、鹵素原子、烷基或者鹵烷基； R12 、R13 、R18 和 R19 相同或者不同且為鹵素原子、C1 ～C6 烷基或者苯基；R14 、R15 、R16 和R17 相同或者不同且為氫原子、鹵素原子、C1 ～C6 烷基或者苯基； R20 、R21 、R22 、R23 、R24 、R25 、R26 和R27 相同或者不同且為鹵素原子、C1 ～C6 烷基、苯基或者氫原子；A為C1 ～C20 的線型、支鏈或者伸環狀烴； R28 和R29 相同或者不同且為鹵素原子、C1 ～C6 烷基或者苯基；R30 和R31 相同或者不同且為氫原子、鹵素原子、C1 ～C6 烷基或者苯基； Z代表具有至少一個碳原子的有機基團； a和b分別為1～30的自然數； 其中，G為雙酚A、雙酚F或共價鍵；m和n分別為1～15的自然數； 所述的乙烯苄基化合物樹脂為乙烯苄基醚化-雙環戊二烯-苯酚樹脂； 所述聚烯烴化合物為苯乙烯-丁二烯-二乙烯基苯共聚物、氫化苯乙烯-丁二烯-二乙烯基苯共聚物、苯乙烯-丁二烯-馬來酸酐共聚物、聚丁二烯-尿酯-甲基丙烯酸甲酯共聚物、苯乙烯-丁二烯共聚物、聚丁二烯均聚物、苯乙烯-異戊二烯-苯乙烯共聚物、苯乙烯-丁二烯-二乙烯基苯共聚物、馬來酸酐化苯乙烯-丁二烯共聚物、甲基苯乙烯共聚物、石油樹脂和環型烯烴共聚物中的至少一種； 所述馬來醯亞胺樹脂為4,4’-雙馬來醯亞胺二苯甲烷、苯甲烷馬來醯亞胺寡聚物、N,N’-間亞苯基雙馬來醯亞胺、雙酚A二苯基醚雙馬來醯亞胺、3,3’-二甲基-5,5’-二乙基-4,4’-二苯基甲烷雙馬來醯亞胺、N,N’-(4-甲基-1,3-亞苯基)雙馬來醯亞胺、1,6-雙馬來醯亞胺-(2,2,4-三甲基)己烷、2,3-二甲基苯馬來醯亞胺、2,6-二甲基苯馬來醯亞胺、N -苯基馬來醯亞胺和上述化合物的預聚體中的至少一種。
- 如請求項1所述的低介電複合材料，其係由以下方法製備而得：將含磷阻燃劑之低介電樹脂組合物溶於溶劑，製成樹脂清漆，以含浸或塗覆方式附著於基材上，並經由高溫加熱形成半固化態，以得到該低介電複合材料。
- 如請求項1所述的低介電複合材料，其係由以下方法製備而得：將含磷阻燃劑之低介電樹脂組合物溶於溶劑，製成樹脂清漆，含浸在纖維材料、織布或不織布上，並經由高溫加熱形成半固化態，以得到半固化片。
- 如請求項1所述的低介電複合材料，其係由以下方法製備而得：將含磷阻燃劑之低介電樹脂組合物溶於溶劑，製成樹脂清漆，塗覆於PET膜或PI膜上，並經由高溫加熱形成半固化態，以得到樹脂膜。
- 如請求項1所述的低介電複合材料，其係由以下方法製備而得：將含磷阻燃劑之低介電樹脂組合物溶於溶劑，製成樹脂清漆，塗覆於銅箔或覆PI膜銅箔的PI膜上，並經由高溫加熱形成半固化態，以得到背膠銅箔。
- 一種積層板，其係由請求項1至9中任一項所述的低介電複合材料製得。
- 一種電路板，其係由請求項10所述的積層板製得。
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| CN103709717B (zh) * | 2013-12-17 | 2017-10-20 | 中山台光电子材料有限公司 | 乙烯苄基醚化‑dopo化合物树脂组合物及制备和应用 |
| CN105542457B (zh) * | 2014-10-30 | 2017-12-15 | 台光电子材料(昆山)有限公司 | 一种低介电耗损树脂组成物及其制品 |
-
2014
- 2014-07-10 CN CN201410328196.7A patent/CN105238000B/zh active Active
- 2014-12-27 TW TW103145874A patent/TWI548520B/zh active
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2015
- 2015-07-07 US US14/793,341 patent/US9872382B2/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI695034B (zh) * | 2015-06-30 | 2020-06-01 | 日商松下知識產權經營股份有限公司 | 硬化性組成物、預浸體、附有組成物之金屬箔、金屬包層層合板、及配線板 |
| TWI722309B (zh) * | 2018-01-08 | 2021-03-21 | 亞洲電材股份有限公司 | 高頻高傳輸雙面銅箔基板、用於軟性印刷電路板之複合材料及其製法 |
| TWI748470B (zh) * | 2020-03-24 | 2021-12-01 | 大陸商中山台光電子材料有限公司 | 樹脂組合物及其製品 |
| TWI898150B (zh) * | 2022-05-24 | 2025-09-21 | 台光電子材料股份有限公司 | 樹脂組合物及其製品 |
| TWI814448B (zh) * | 2022-06-16 | 2023-09-01 | 南亞塑膠工業股份有限公司 | 高導熱低介電橡膠樹脂材料及應用其的金屬基板 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105238000A (zh) | 2016-01-13 |
| US9872382B2 (en) | 2018-01-16 |
| TWI548520B (zh) | 2016-09-11 |
| CN105238000B (zh) | 2017-08-25 |
| US20160021739A1 (en) | 2016-01-21 |
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