JP6846540B2 - 熱硬化性樹脂組成物、それにより製造したプリプレグ、金属箔張積層板及び高周波回路基板 - Google Patents
熱硬化性樹脂組成物、それにより製造したプリプレグ、金属箔張積層板及び高周波回路基板 Download PDFInfo
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- JP6846540B2 JP6846540B2 JP2019557861A JP2019557861A JP6846540B2 JP 6846540 B2 JP6846540 B2 JP 6846540B2 JP 2019557861 A JP2019557861 A JP 2019557861A JP 2019557861 A JP2019557861 A JP 2019557861A JP 6846540 B2 JP6846540 B2 JP 6846540B2
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- 229920001187 thermosetting polymer Polymers 0.000 title claims description 55
- 239000011342 resin composition Substances 0.000 title claims description 54
- 229910052751 metal Inorganic materials 0.000 title claims description 11
- 239000002184 metal Substances 0.000 title claims description 11
- 229920005989 resin Polymers 0.000 claims description 104
- 239000011347 resin Substances 0.000 claims description 104
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 82
- 229910052698 phosphorus Inorganic materials 0.000 claims description 82
- 239000011574 phosphorus Substances 0.000 claims description 82
- 229920001955 polyphenylene ether Polymers 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 19
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000000843 powder Substances 0.000 claims description 15
- 238000004132 cross linking Methods 0.000 claims description 14
- 239000000945 filler Substances 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 230000001070 adhesive effect Effects 0.000 claims description 9
- 239000000853 adhesive Substances 0.000 claims description 8
- 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 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 5
- 239000012779 reinforcing material Substances 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- JUIBLDFFVYKUAC-UHFFFAOYSA-N [5-(2-ethylhexanoylperoxy)-2,5-dimethylhexan-2-yl] 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C(CC)CCCC JUIBLDFFVYKUAC-UHFFFAOYSA-N 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
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- 239000005011 phenolic resin Substances 0.000 description 21
- 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 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 229920001568 phenolic resin Polymers 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 239000004744 fabric Substances 0.000 description 11
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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- 239000003365 glass fiber Substances 0.000 description 9
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical group C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 238000006462 rearrangement reaction Methods 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- -1 polytetrafluoroethylene Polymers 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000000835 fiber Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000013557 residual solvent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical group C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
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- 239000003444 phase transfer catalyst Substances 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 238000005937 allylation reaction Methods 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
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- 238000002844 melting Methods 0.000 description 3
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- 230000007935 neutral effect Effects 0.000 description 3
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- 230000035484 reaction time Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- SCZZNWQQCGSWSZ-UHFFFAOYSA-N 1-prop-2-enoxy-4-[2-(4-prop-2-enoxyphenyl)propan-2-yl]benzene Chemical compound C=1C=C(OCC=C)C=CC=1C(C)(C)C1=CC=C(OCC=C)C=C1 SCZZNWQQCGSWSZ-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910002113 barium titanate Inorganic materials 0.000 description 2
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical group C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
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- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
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- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
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- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 description 1
- LMWMTSCFTPQVCJ-UHFFFAOYSA-N 2-methylphenol;phenol Chemical compound OC1=CC=CC=C1.CC1=CC=CC=C1O LMWMTSCFTPQVCJ-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
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- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- MSINWGGINAXXLP-UHFFFAOYSA-N CCc1cc([Po-]2(C3=CCCC=C3C3C=CC=CC23)=O)ccc1 Chemical compound CCc1cc([Po-]2(C3=CCCC=C3C3C=CC=CC23)=O)ccc1 MSINWGGINAXXLP-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- LJUXFZKADKLISH-UHFFFAOYSA-N benzo[f]phosphinoline Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=P1 LJUXFZKADKLISH-UHFFFAOYSA-N 0.000 description 1
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- SXGBREZGMJVYRL-UHFFFAOYSA-N butan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH3+] SXGBREZGMJVYRL-UHFFFAOYSA-N 0.000 description 1
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- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
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- 150000002013 dioxins Chemical class 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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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
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- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Description
一方、本発明は、熱硬化性樹脂組成物を提供しており、前記熱硬化性樹脂組成物は、熱硬化性成分を含み、前記熱硬化性成分は、リン含有モノマー又はリン含有樹脂及び不飽和基含有ポリフェニレンエーテル樹脂を含み、前記リン含有モノマー又はリン含有樹脂は、式Iで示される構造を有し、
ただし、Rは、直鎖又は分岐鎖アルキル基、
または
または
または
または
ただし、nは、1〜20の整数である。
(1)式IIで示されるフェノール系化合物又はフェノール系樹脂とアリル化試薬とを反応させて式IIIで示されるアリルエーテル化樹脂を得て、反応式の例は以下の通りであり、
または
または
または
または
又は
好ましくは、前記不飽和基含有ポリフェニレンエーテル樹脂の数平均分子量は700〜8000であり、例えば、700、900、1200、1500、2000、3000、4000、5000、6000、7000又は8000であり、より好ましくは900〜5000であり、更に好ましくは1000〜3500である。本発明において、前記不飽和基(例えば、二重結合、三重結合)含有ポリフェニレンエーテル樹脂は、良好な反応性を有し、適当な分子量を制御することにより良好な溶解性及び低い溶融粘度を提供でき、後続する浸漬プロセスの操作及び積層流動が容易であり、更に多層回路基板の加工工程に接着剤充填能力を提供できる。
(1)本発明に係る樹脂に極性水酸基を含まず、且つ分子構造が安定し、分子極性が低く、反応活性が高い特徴を有し、その応用の加工工程にも極性水酸基が生じることがなく、生成された二次水酸基のその生成物への影響を回避するため、当該樹脂は誘電性能を向上すると同時に架橋反応可能な基も有し、これにより硬化後の耐高温性能が著しい変化せず、リン含有末端封止基を導入することにより、樹脂は固有の難燃性能を有し、そして前記リン含有モノマー又はリン含有樹脂は、良好な溶解性能、相対的低い溶融粘度を有し、熱硬化性樹脂組成物に良好なプロセス加工性能を付与する。
三口フラスコに188gのアセトンを添加し、228gのビスフェノールAをフラスコに添加し、撹拌して溶解させた後に、106gの炭酸ナトリウムを添加した。153gの塩化アリル溶液をゆっくりと滴下してから、昇温して4時間反応させて反応を停止させた。ろ過して大部分の溶媒を除去し、洗淨して残留した溶媒及び水を除去し、ビスフェノールAジアリルエーテルを得た。
三口フラスコに300gのn−ブタノールを添加し、114gのノボラック樹脂をフラスコに添加し、撹拌して溶解させた後に、56gの水酸化カリウムを添加した。153gの臭化プロペニル溶液をゆっくりと滴下してから、昇温して4時間反応させて反応を停止させた。ろ過して洗淨し、残留した溶媒及び水を除去し、アリルエーテル化フェノール樹脂を得た。
三口フラスコに250gのトルエンを添加し、118gのo−クレゾールフェノール樹脂をフラスコに添加し、撹拌して溶解させた後に、100gの水酸化ナトリウム水溶液(濃度40%)を添加し、さらに1gのテトラブチルアンモニウムブロマイドを添加した。温度が一定になった後、153gの塩化アリル溶液をゆっくりと滴下してから、昇温して4時間反応させて反応を停止し、洗淨して溶媒を除去し、アリルエーテル化オルソクレゾールフェノール樹脂を得た。
80重量部のSA9000、20重量部の調製例1で製造されたリン含有エステル化ジアリルビスフェノールA、85重量部のシリカ(525)、6.5重量部の開始剤DCPを混合し、トルエン溶媒を用いて適当な粘度に調整し、フィラーを樹脂に均一に分散するように攪拌して均一に混合し、接着液を製造した。1080ガラス繊維布を上記接着液で浸漬させてから、乾燥させて溶媒を除去した後に、プリプレグを製造した。8枚の製造したプリプレグを重ね合わせて、その両側に厚み1oz(オンス)の銅箔を積層し、ラミネータで2時間硬化させ、硬化圧力は50kg/cm2であり、硬化温度は190℃であり、物性データを表2に示す。
製造プロセスは実施例1と同様であり、熱硬化性樹脂組成物の配合割合を表2に示すように変更し、銅張板を製造し、その性能データを表2に示す。
製造プロセスは実施例1と同様であり、架橋助剤のビスマレイミドを添加し、その樹脂組成物の成分配合割合及び製造した銅張板の性能データを表2に示す。
80重量部のOPE−ST−1200、20重量部の調製例2で製造されたリン含有エステル化アリルフェノール樹脂、85重量部のシリカ(525)、6.5重量部の開始剤DCPを混合し、トルエン溶媒を用いて適当な粘度に調整し、フィラーを樹脂に均一に分散するように攪拌して均一に混合し、接着液を製造した。1080ガラス繊維布を上記接着液で浸漬させてから、乾燥させて溶媒を除去した後に、プリプレグを製造した。8枚の製造したプリプレグを重ね合わせて、その両側に厚み1oz(オンス)の銅箔を積層し、ラミネータで2時間硬化させ、硬化圧力は50kg/cm2であり、硬化温度は190℃であり、物性データを表2に示す。
製造プロセスは実施例1と同様であり、ただ少量のリン含有エステル化ジアリルビスフェノールAを添加し、材料配合割合及び製造した銅張板の性能データを表2に示す。
製造プロセスは実施例1と同様であり、リン含有エステル化ジアリルビスフェノールAを除去するか、又はリン含有エステル化アリルフェノール樹脂の代わりとしてアリルフェノール樹脂及びDOPO難燃剤を用いて、材料配合割合及び製造した銅張板の性能データを表2に示す。
表2の物性データ結果から、実施例1〜6で製造された銅張板は、比較例1及び比較例2で製造された銅張板と比較して、より良好な耐熱性能、耐ディップはんだ付け性及び難燃性能を有することが分かった。
Claims (17)
- 前記リン含有モノマー又はリン含有樹脂はリン含有量が3%を超えるリン含有モノマー又はリン含有樹脂である、ことを特徴とする請求項1に記載の熱硬化性樹脂組成物。
- 前記不飽和基含有ポリフェニレンエーテル樹脂は、二重結合又は三重結合を含むポリフェニレンエーテル樹脂である、ことを特徴とする請求項1〜3のいずれか一項に記載の熱硬化性樹脂組成物。
- 前記不飽和基含有ポリフェニレンエーテル樹脂は、アリル基末端封止ポリフェニレンエーテル樹脂、アクリレート末端封止ポリフェニレンエーテル樹脂及びビニル末端封止ポリフェニレンエーテル樹脂のいずれか1種又は少なくとも2種の組合せである、ことを特徴とする請求項4に記載の熱硬化性樹脂組成物。
- 前記不飽和基含有ポリフェニレンエーテル樹脂の数平均分子量は700〜8000である、ことを特徴とする請求項1〜5のいずれか一項に記載の熱硬化性樹脂組成物。
- 前記熱硬化性成分が前記熱硬化性樹脂組成物に占める重量百分率は5〜90%である、ことを特徴とする請求項1〜6のいずれか一項に記載の熱硬化性樹脂組成物。
- 前記熱硬化性樹脂組成物は、粉末フィラーを更に含み、
前記粉末フィラーのメディアン径は1〜15μmであり、
前記粉末フィラーが熱硬化性樹脂組成物に占める重量百分率は0%〜50%である、ことを特徴とする請求項1〜7のいずれか一項に記載の熱硬化性樹脂組成物。 - 前記熱硬化性樹脂組成物は硬化開始剤を更に含み、
前記硬化開始剤の用量が熱硬化性樹脂組成物に占める質量百分率は0.3〜6%であり、
前記硬化開始剤は過酸化ベンゾイル、ジクミルパーオキサイド、t−ブチルパーオキシベンゾエート及び2,5−ビス(2−エチルヘキサノイルペルオキシ)−2,5−ジメチルヘキサンのいずれか1種又は少なくとも2種の組合せである、ことを特徴とする請求項1〜8のいずれか一項に記載の熱硬化性樹脂組成物。 - 前記熱硬化性樹脂組成物は架橋助剤を更に含み、前記架橋助剤は、分子構造に不飽和二重結合又は不飽和三重結合を有するモノマー又は低分子共重合体である、ことを特徴とする請求項1〜9のいずれか一項に記載の熱硬化性樹脂組成物。
- 前記架橋助剤は、トリアリルイソシアヌレート、トリアリルシアヌレート、ジビニルベンゼン、多官能アクリレート及びビスマレイミドのいずれか1種又は少なくとも2種の組合せである、ことを特徴とする請求項10に記載の熱硬化性樹脂組成物。
- 前記熱硬化性樹脂組成物は他の熱硬化性樹脂を更に含み、前記他の熱硬化性樹脂は、不飽和二重結合又は不飽和三重結合を有する樹脂材料である、ことを特徴とする請求項1〜11のいずれか一項に記載の熱硬化性樹脂組成物。
- 請求項1〜12のいずれか一項に記載の熱硬化性樹脂組成物を溶剤に溶解又は分散させて得られる、ことを特徴とする樹脂接着液。
- 補強材料と、浸漬し乾燥させることで補強材料に付着している請求項1〜12のいずれか一項に記載の熱硬化性樹脂組成物とを含む、ことを特徴とするプリプレグ。
- 少なくとも請求項14に記載のプリプレグを含む、ことを特徴とする積層板。
- 1枚又は少なくとも2枚の重ね合せた請求項14に記載のプリプレグと、重ね合せたプリプレグの一側又は両側に位置する金属箔とを含む、ことを特徴とする金属箔張積層板。
- 1枚又は少なくとも2枚の重ね合せた請求項14に記載のプリプレグを含む、ことを特徴とする高周波回路基板。
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CN106543228B (zh) | 2016-10-25 | 2018-07-17 | 北京工商大学 | 一种含磷杂菲基团的烷基次膦酸盐衍生物阻燃剂及其制备方法 |
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JP2020519707A (ja) | 2020-07-02 |
CN109306171A (zh) | 2019-02-05 |
KR20200021078A (ko) | 2020-02-27 |
KR102282601B1 (ko) | 2021-07-29 |
TW201910427A (zh) | 2019-03-16 |
US20200224026A1 (en) | 2020-07-16 |
CN109306171B (zh) | 2021-01-01 |
WO2019019464A1 (zh) | 2019-01-31 |
TWI658095B (zh) | 2019-05-01 |
US11377551B2 (en) | 2022-07-05 |
EP3660027A4 (en) | 2021-04-28 |
EP3660027A1 (en) | 2020-06-03 |
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