CN112313265A - Resin composition and use thereof - Google Patents
Resin composition and use thereof Download PDFInfo
- Publication number
- CN112313265A CN112313265A CN201980042158.6A CN201980042158A CN112313265A CN 112313265 A CN112313265 A CN 112313265A CN 201980042158 A CN201980042158 A CN 201980042158A CN 112313265 A CN112313265 A CN 112313265A
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- CN
- China
- Prior art keywords
- resin composition
- compound
- mass
- group
- resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000011342 resin composition Substances 0.000 title claims abstract description 187
- -1 bismaleimide compound Chemical class 0.000 claims abstract description 217
- 229920005989 resin Polymers 0.000 claims abstract description 102
- 239000011347 resin Substances 0.000 claims abstract description 102
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 229920003192 poly(bis maleimide) Polymers 0.000 claims abstract description 77
- 239000004643 cyanate ester Substances 0.000 claims abstract description 58
- 229910052751 metal Inorganic materials 0.000 claims abstract description 38
- 239000002184 metal Substances 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 claims abstract description 24
- 125000000962 organic group Chemical group 0.000 claims abstract description 12
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 7
- 239000003822 epoxy resin Substances 0.000 claims description 51
- 229920000647 polyepoxide Polymers 0.000 claims description 51
- 239000002904 solvent Substances 0.000 claims description 45
- 229920001955 polyphenylene ether Polymers 0.000 claims description 41
- 239000005011 phenolic resin Substances 0.000 claims description 40
- 239000000463 material Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 33
- 229920001971 elastomer Polymers 0.000 claims description 28
- 239000000806 elastomer Substances 0.000 claims description 25
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 24
- 239000000945 filler Substances 0.000 claims description 20
- 239000011888 foil Substances 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 15
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000005462 imide group Chemical group 0.000 claims description 10
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 9
- 125000004185 ester group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 239000004020 conductor Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 47
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000011521 glass Substances 0.000 description 37
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- 239000002966 varnish Substances 0.000 description 22
- 239000011889 copper foil Substances 0.000 description 20
- 229920003986 novolac Polymers 0.000 description 20
- 238000012360 testing method Methods 0.000 description 19
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 14
- 229910052802 copper Inorganic materials 0.000 description 13
- 239000010949 copper Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 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 11
- 238000000576 coating method Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 8
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 238000005452 bending Methods 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000005530 etching Methods 0.000 description 8
- 229920001568 phenolic resin Polymers 0.000 description 8
- 230000004580 weight loss Effects 0.000 description 8
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 108091063785 miR-3000 stem-loop Proteins 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical group C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 5
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical class O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 5
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 4
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 150000005130 benzoxazines Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 238000010030 laminating Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 4
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 4
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 229920002050 silicone resin Polymers 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RNIPJYFZGXJSDD-UHFFFAOYSA-N 2,4,5-triphenyl-1h-imidazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 RNIPJYFZGXJSDD-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000005691 oxidative coupling reaction Methods 0.000 description 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 3
- 229960001553 phloroglucinol Drugs 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- MTJUELTVQKBEPR-UHFFFAOYSA-N 2-(chloromethyl)oxetane Chemical compound ClCC1CCO1 MTJUELTVQKBEPR-UHFFFAOYSA-N 0.000 description 2
- VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RESAGKWBLNVCPV-UHFFFAOYSA-N C=CC.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical compound C=CC.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 RESAGKWBLNVCPV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
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- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- UQLDLKMNUJERMK-UHFFFAOYSA-L di(octadecanoyloxy)lead Chemical compound [Pb+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O UQLDLKMNUJERMK-UHFFFAOYSA-L 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- SGLXWMAOOWXVAM-UHFFFAOYSA-L manganese(2+);octanoate Chemical compound [Mn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O SGLXWMAOOWXVAM-UHFFFAOYSA-L 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- ROEHNQZQCCPZCH-UHFFFAOYSA-N tert-butyl 2-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OC(C)(C)C ROEHNQZQCCPZCH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 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
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Providing: a resin composition having excellent properties such as heat resistance and excellent electrical characteristics, a cured product, a prepreg, a metal foil-clad laminate, a resin sheet, a printed wiring board, a method for producing a resin composition, and a dielectric constant and/or dielectric loss tangent reducing agent. A resin composition comprising: a cyanate ester compound (A) and a bismaleimide compound (B) represented by formula (1); in the formula (1), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each of which isIndependently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each a independently represents an integer of 0 to 4.
Description
Technical Field
The present invention relates to a resin composition. Further, the present invention relates to a cured product, a prepreg, a metal foil-clad laminate, a resin sheet, a printed wiring board, a method for producing a resin composition, and a dielectric constant and/or dielectric loss tangent reducing agent using the resin composition.
Background
In recent years, high integration and miniaturization of semiconductors used for electronic devices, communication devices, personal computers, and the like have been accelerated. Accordingly, the characteristics required for a laminate for a semiconductor package (for example, a metal foil-clad laminate) used for a printed wiring board have become more severe. Examples of the required properties include low dielectric constant, low dielectric loss tangent, low thermal expansion, and heat resistance. Among them, an insulator material having a large dielectric constant and a large dielectric loss tangent attenuates an electric signal, and a material having a small dielectric constant and a small dielectric loss tangent is required in order not to impair reliability.
In order to obtain a printed wiring board with improved properties, studies have been made on materials used as materials for printed wiring boards. For example, patent document 1 discloses, as a composition which is excellent in storage stability of varnish and which is improved in electrical characteristics, peel strength and thermal decomposition resistance without lowering multilayer moldability and heat resistance after moisture absorption, the following composition: the composition is prepared by combining a 2-functional vinylbenzyl compound containing a specific polyphenylene ether skeleton, a specific maleimide compound, a specific cyanate ester resin and a specific epoxy resin at a predetermined ratio.
On the other hand, patent document 2 discloses a prepreg including: bismaleimides having a specific structure, 1 or more liquid coreactants containing (b) optionally additional other additives, and (c) structural fibers are also possible. However, no description is given of electrical characteristics and the like.
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent application No. 2010-138364
Patent document 2: japanese laid-open patent publication No. H05-25298
Disclosure of Invention
Problems to be solved by the invention
As described above, a resin composition containing a cyanate ester compound and a maleimide compound, which is excellent in electrical characteristics, is known. However, with recent technological innovation, further improvement in electrical characteristics is required. In addition, even if the electrical characteristics are excellent, if the other properties are poor, the usefulness is poor.
An object of the present invention is to solve the above problems, and to provide: a resin composition which comprises a cyanate ester compound and a maleimide compound, has excellent various properties such as heat resistance, and has excellent electrical characteristics; and a cured product, a prepreg, a metal foil-clad laminate, a resin sheet, a printed wiring board, a method for producing a resin composition, and an agent for reducing the dielectric constant and/or dielectric loss tangent.
Means for solving the problems
Based on the above problems, the present inventors have conducted studies and found that: the present inventors have completed the present invention by finding that a resin composition having improved electrical characteristics and excellent in various properties such as heat resistance can be obtained by using a bismaleimide compound having a specific structure. Specifically, the aforementioned problems can be solved by the following means <1>, preferably < 2> - <18 >.
<1> a resin composition comprising:
cyanate ester compound (A), and
a bismaleimide compound (B) represented by the following formula (1);
in the formula (1), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each independently represents an integer of 0 to 4.
<2>According to<1>The resin composition is characterized in that in the formula (1), X is alkylene with 1-3 carbon atoms, and R1~R3Each independently represents a hydrogen atom, a methyl group or an ethyl group, and each independently represents an integer of 0 to 2.
<3> the resin composition according to <1>, wherein the bismaleimide compound (B) is represented by the following formula (2).
<4> the resin composition according to any one of <1> to <3>, which further contains a solvent.
<5> the resin composition according to <4>, wherein the content of the bismaleimide compound (B) is 0.1 to 30% by mass of the resin composition.
<6> the resin composition according to any one of <1> to <5>, wherein the content ratio of the cyanate ester compound (A) and the bismaleimide compound (B) is 0.01 or more and less than 1.1 as represented by an equivalent ratio of an unsaturated imide group of the bismaleimide compound (B) to a cyanate ester group of the cyanate ester compound (A) (equivalent of an unsaturated imide group/equivalent of a cyanate ester group).
<7> the resin composition according to any one of <1> to <6>, which further contains 1 or more selected from the group consisting of a maleimide compound other than the bismaleimide compound (B), an epoxy resin, a phenolic resin, an oxetane resin, a benzoxazine compound, a compound having a polymerizable unsaturated group, a modified polyphenylene ether end-modified with a substituent containing a carbon-carbon unsaturated double bond (other than maleimide), an elastomer and an active ester compound.
<8> the resin composition according to any one of <1> to <7>, which further contains a filler (C).
<9> the resin composition according to <8>, wherein the content of the filler (C) is 50 to 1600 parts by mass based on 100 parts by mass of the total amount of the resin components in the resin composition.
<10> the resin composition according to any one of <1> to <9>, which is a low dielectric constant material and/or a low dielectric loss tangent material.
<11> A cured product of the resin composition according to any one of <1> to <10 >.
<12> a prepreg comprising a substrate and the resin composition according to any one of <1> to <10 >.
<13> a metal-foil-clad laminate comprising: a layer formed from at least 1 sheet of the prepreg of <12 >; and a metal foil disposed on one or both surfaces of the layer formed of the prepreg.
<14> a resin tablet comprising: a support body; and a layer formed of the resin composition according to any one of <1> to <10> and disposed on the surface of the support.
<15> a printed circuit board comprising: an insulating layer and a conductor layer disposed on the surface of the insulating layer,
the insulating layer includes: at least one of a layer formed from the resin composition according to any one of <1> to <10> and a layer formed from the prepreg according to <12 >.
<16> a method for producing a resin composition comprising a cyanate ester compound (A) and a bismaleimide compound (B) represented by the following formula (1),
the manufacturing method comprises the following steps: mixing a cyanate ester compound (A), a bismaleimide compound (B) and a solvent, wherein the content of the bismaleimide compound (B) is 0.1-30% by mass of the resin composition;
in the formula (1), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each independently represents an integer of 0 to 4.
<17> the method for producing a resin composition according to <16>, wherein the resin composition further contains 1 or more selected from the group consisting of maleimide compounds other than the bismaleimide compound (B), epoxy resins, phenol resins, oxetane resins, benzoxazine compounds, compounds having polymerizable unsaturated groups, modified polyphenylene ethers end-modified with substituents containing carbon-carbon unsaturated double bonds (other than maleimide), elastomers, and active ester compounds.
<18> a dielectric constant and/or dielectric loss tangent reducing agent comprising a bismaleimide compound (B) represented by the following formula (1);
in the formula (1), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each independently represents an integer of 0 to 4.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, there can be provided: the resin composition comprises a cyanate ester compound and a maleimide compound, and has excellent properties such as heat resistance and excellent electrical characteristics. Further, there can be provided: excellent cured product, prepreg, metal foil-clad laminate, resin sheet, printed wiring board, method for producing resin composition, and agent for reducing dielectric constant and/or dielectric loss tangent.
Detailed Description
The present invention will be described in detail below. In the present specification, "to" is used in a meaning including numerical values described before and after the "to" as a lower limit value and an upper limit value.
The resin composition of the present invention is characterized by containing a cyanate ester compound (a) and a bismaleimide compound (B) represented by the following formula (1).
In the formula (1), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each independently represents an integer of 0 to 4.
By blending the bismaleimide compound (B) represented by the formula (1) with the cyanate ester compound (a), the dielectric constant (Dk) and the dielectric loss tangent (Df) can be reduced while maintaining various performances (low water absorption, low weight loss on heating, and good appearance of the varnish). Further, the appearance in the case of forming a prepreg, the peel strength, heat resistance, flame retardancy, and the like in the case of forming a metal foil-clad laminate can be maintained at a high level.
The present invention will be described in detail below using an embodiment of the present invention (hereinafter, also referred to as "the present embodiment") as an example.
< cyanate ester Compound (A) >)
The cyanate ester compound (a) in the present embodiment is not particularly limited as long as it has a cyanate ester structure.
Examples of the cyanate ester compound (a) include at least 1 selected from the group consisting of naphthol aralkyl type cyanate ester compounds (naphthol aralkyl type cyanate esters), naphthylene ether type cyanate ester compounds, xylene resin type cyanate ester compounds, triphenylolmethane type cyanate ester compounds, and adamantane skeleton type cyanate ester compounds. Among these, from the viewpoint of further improving the plating adhesion and the low water absorption property, at least 1 selected from the group consisting of naphthol aralkyl type cyanate ester compounds, naphthylene ether type cyanate ester compounds, and xylene resin type cyanate ester compounds is preferable, and naphthol aralkyl type cyanate ester compounds are more preferable. These cyanate ester compounds can be prepared by a known method, and commercially available products can be used. The cyanate ester compound having a naphthol aralkyl skeleton, a naphthylene ether skeleton, a xylene skeleton, a triphenylolmethane skeleton or an adamantane skeleton tends to have a further reduced water absorption because the number of functional groups is large and unreacted cyanate groups are small. In addition, since the coating material mainly has an aromatic skeleton or an adamantane skeleton, the coating adhesion tends to be further improved.
The equivalent weight of the cyanate group of the cyanate ester compound (A) is preferably 200g/eq or more, and preferably 400g/eq or less. When a plurality of cyanate ester compounds (a) are contained, the equivalent weight of the cyanate ester group is regarded as a weighted average in consideration of the mass of each cyanate ester compound contained in the resin composition.
The lower limit of the content of the cyanate ester compound (a) is preferably 1 part by mass or more, more preferably 10 parts by mass or more, further preferably 20 parts by mass or more, further preferably 30 parts by mass or more, and may be 40 parts by mass or more, with respect to 100 parts by mass of the total amount of the resin components in the resin composition. The cyanate ester compound content is 1 part by mass or more, more preferably 10 parts by mass or more, and the heat resistance, the combustion resistance, the chemical resistance, the low dielectric constant, the low dielectric loss tangent, and the insulation properties tend to be improved. The upper limit of the content of the cyanate ester compound is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, further preferably 70 parts by mass or less, and further preferably 60 parts by mass or less, with respect to 100 parts by mass of the total amount of the resin components in the resin composition.
The resin composition in the present embodiment may contain only 1 kind of cyanate ester compound, or may contain 2 or more kinds of cyanate ester compounds. When 2 or more species are contained, the total amount is preferably within the above range.
< bismaleimide Compound (B) represented by the formula (1) >)
The resin composition of the present embodiment contains a bismaleimide compound (B) represented by the following formula (1).
In the formula (1), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each independently represents an integer of 0 to 4.
In the formula (1), X represents an organic group having 1 to 12 carbon atoms, preferably an alkylene group having 1 to 3 carbon atoms, and more preferably an isopropylidene group. The 2 xs may be the same or different. Preferably the same.
R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably a hydrogen atom, a methyl group or an ethyl group, and more preferably a hydrogen atom.
a preferably represents an integer of 0 to 2, more preferably 0 or 1, and further preferably 0.
The bismaleimide compound (B) is preferably represented by the formula (1-2).
In the formula (1-2), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each independently represents an integer of 0 to 4.
X, R in formula (1-2)1~R3And a are respectively X, R in the formula (1)1~R3And a are the same, and the same applies to preferred ranges. By using the bismaleimide compound represented by the formula (1-2), the electrical characteristics and heat resistance (particularly, suppression of weight loss on heating) of the resin composition tend to be further improved.
The bismaleimide compound (B) represented by the formula (1) is also preferably represented by the following formula (2).
The bismaleimide compound (B) used in the present embodiment is more preferably any of the following compounds.
The equivalent of the unsaturated imide group in the bismaleimide compound (B) is preferably 200g/eq or more, and more preferably 400g/eq or less. When a plurality of bismaleimide compounds (B) are contained, the equivalent weight of the unsaturated imide group is regarded as a weighted average in consideration of the mass of each bismaleimide compound (B) contained in the resin composition.
The lower limit of the content of the bismaleimide compound (B) is preferably 1 part by mass or more, more preferably 3 parts by mass or more, further preferably 5 parts by mass or more, and further may be 8 parts by mass or more, 10 parts by mass or more, or 15 parts by mass or more, with respect to 100 parts by mass of the total amount of the resin components in the resin composition. The content of the bismaleimide compound (B) is 1 part by mass or more, and thus the flame resistance tends to be improved. When the bismaleimide compound (B) is contained, the upper limit of the content of the bismaleimide compound (B) is preferably 90 parts by mass or less, more preferably 75 parts by mass or less, further preferably 60 parts by mass or less, further preferably 45 parts by mass or less, further preferably 35 parts by mass or less, and further preferably 30 parts by mass or less, based on 100 parts by mass of the total amount of the resin components in the resin composition.
The content of the bismaleimide compound (B) is preferably 0.1 to 30% by mass of the resin composition.
In particular, the lower limit of the content of the bismaleimide compound (B) is preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably 20% by mass or more, relative to the solid content (components other than the solvent). The upper limit is preferably 90% by mass or less, more preferably 70% by mass or less, and still more preferably 50% by mass or less.
The content of the bismaleimide compound (B) is preferably 0.1 to 30% by mass in the resin composition (resin composition containing a solvent) diluted with the solvent. The lower limit of the content of the bismaleimide compound (B) is preferably 1% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more. The upper limit is preferably 25% by mass or less, more preferably 20% by mass or less, and still more preferably 17.5% by mass or less.
By setting the range as described above, the varnish appearance, the appearance when the prepreg is formed, and the electrical characteristics of the laminate can be further improved.
The resin composition of the present embodiment may contain only 1 kind of bismaleimide compound (B), or may contain 2 or more kinds of bismaleimide compounds (B). When 2 or more species are contained, the total amount is preferably within the above range.
The resin composition of the present embodiment may contain only 1 kind of bismaleimide compound (B), or may contain 2 or more kinds of bismaleimide compounds (B). When 2 or more species are contained, the total amount is preferably within the above range.
The content ratio of the cyanate ester compound (a) and the bismaleimide compound (B) in the resin composition of the present embodiment is preferably 0.01 or more and less than 1.1, as represented by an equivalent ratio of an unsaturated imide group of the bismaleimide compound (B) to a cyanate group of the cyanate ester compound (a) (equivalent of the unsaturated imide group/equivalent of the cyanate group). The lower limit of the equivalent ratio is more preferably 0.05 or more, still more preferably 0.1 or more, and still more preferably 0.3 or more. The upper limit of the equivalent ratio is more preferably 0.9 or less, still more preferably 0.7 or less, and still more preferably 0.5 or less. By setting the range as described above, the effects of water absorption, electric characteristics, and thermophysical properties can be more effectively exhibited.
< other resin component >
The resin composition of the present embodiment may contain other resin components than the cyanate ester compound (a) and the bismaleimide compound (B). Examples of the other resin component include a compound selected from the group consisting of maleimide compounds other than bismaleimide compound (B), epoxy resins, phenol resins, oxetane resins, benzoxazine compounds, compounds having polymerizable unsaturated groups, modified polyphenylene ethers end-modified with a substituent containing a carbon-carbon unsaturated double bond (other than maleimide), the elastomer and the active ester compound are preferably 1 or more selected from the group consisting of maleimide compounds other than the bismaleimide compound (B), epoxy resins, phenol resins, oxetane resins, benzoxazine compounds, and compounds having polymerizable unsaturated groups, and more preferably include at least maleimide compounds other than the bismaleimide compound (B). By blending such other resin components, the appearance can be further improved, and other properties can be further improved.
Maleimide compound other than bismaleimide compound (B) >)
The maleimide compound other than the bismaleimide compound (B) (hereinafter, also referred to as another maleimide compound) is not particularly limited as long as it is a maleimide compound other than the bismaleimide compound (B) and is a compound having 2 or more maleimide groups in the molecule. In particular, by using a maleimide compound having high solubility in a solvent, it is possible to improve the electrical characteristics, to improve the appearance of a varnish, and to further improve the appearance of a prepreg obtained from the varnish. The other maleimide compound used in the present embodiment has a solubility in methyl ethyl ketone at 25 ℃ of preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably 20% by mass or more. Since methyl ethyl ketone has a low boiling point, the drying temperature can be lowered when the solvent is dried, and unnecessary curing of the resin component during drying can be effectively suppressed.
As another example of the maleimide compound, a maleimide compound represented by the formula (1-3) can be mentioned. By using the maleimide compound represented by the formula (1-3), when used for a material for a printed wiring board (for example, a laminate, a metal foil-clad laminate) or the like, excellent heat resistance can be imparted, and peel strength, low water absorption, resistance to removal of surface stains, and flame resistance can be improved.
In the formula (1-3), a plurality of R independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a phenyl group, and n represents 1< n.ltoreq.5.
In the formula (1-3), R's present in plural are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms (e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, etc.), or a phenyl group. Among these, from the viewpoint of further improving flame resistance and peel strength, a group selected from the group consisting of a hydrogen atom, a methyl group and a phenyl group is preferable, one of a hydrogen atom and a methyl group is more preferable, and a hydrogen atom is further preferable.
In the above formula (1-3), n is an average value and represents 1< n.ltoreq.5. From the viewpoint of further excellent solvent solubility, n is preferably 4 or less, more preferably 3 or less, and further preferably 2 or less. More than 2 different compounds of n may be included.
The maleimide compound represented by the above formula (1-3) can be produced by a known method, or a commercially available compound can be used. Examples of commercially available products include "MIR-3000" manufactured by Nippon Kabushiki Kaisha.
In addition to the above, examples of the other maleimide compounds include 4,4 ' -5,5 ' -diethyl-4, 4 ' -diphenylmethane bismaleimide, 4-methyl-1, 3-phenylenebismaleimide, 1, 6-bismaleimide- (2,2, 4-trimethyl) hexane, 4 ' -diphenyl ether bismaleimide, 4 ' -diphenylsulfone bismaleimide, 1, 3-bis (3-maleimidophenoxy) benzene, 1, 3-bis (4-maleimidophenoxy) benzene, polyphenylmethane maleimide, prepolymers thereof, and prepolymers of these maleimides with amines.
The equivalent of the unsaturated imide group in the other maleimide compound is preferably 200g/eq or more, and preferably 400g/eq or less. When a plurality of other maleimide compounds are contained, the equivalent weight of the unsaturated imide group is regarded as a weighted average in consideration of the mass of each other maleimide compound contained in the resin composition.
The lower limit of the content of the other maleimide compound is preferably 1 part by mass or more, more preferably 10 parts by mass or more, and further preferably 20 parts by mass or more, based on 100 parts by mass of the total amount of the resin components in the resin composition, in the case where the other maleimide compound is contained. The content of the other maleimide compound is 1 part by mass or more, and the flame resistance of the resin composition tends to be improved. When the other maleimide compound is contained, the upper limit of the content of the other maleimide compound is preferably 90 parts by mass or less, more preferably 85 parts by mass or less, still more preferably 75 parts by mass or less, yet more preferably 70 parts by mass or less, yet more preferably 60 parts by mass or less, yet more preferably 55 parts by mass or less, and particularly preferably 45 parts by mass or less, based on 100 parts by mass of the total amount of the resin components in the resin composition. The content of the other maleimide compound is 90 parts by mass or less, and the peel strength and the low water absorption tend to be improved.
The resin composition in the present embodiment particularly preferably contains both the bismaleimide compound represented by the formula (1) and the maleimide compound represented by the formula (1-3). The mass ratio of the bismaleimide compound represented by the formula (1) to the maleimide compound represented by the formula (1-3) in the resin composition is preferably 1: 0.1 to 2.0, more preferably 1: 1.0 to 2.0, and more preferably 1: 1.2 to 1.8, preferably 1: 1.4 to 1.6. By setting such a ratio, the appearance of the varnish obtained and the electrical characteristics of the cured product can be satisfied at the same time with a high degree of dimension.
The resin composition in the present embodiment may contain only 1 kind of other maleimide compound, or may contain 2 or more kinds of other maleimide compounds. When 2 or more species are contained, the total amount is preferably within the above range.
< epoxy resin >)
The epoxy resin is not particularly limited as long as it is a compound or resin having 2 or more epoxy groups in 1 molecule.
Examples of the epoxy resin include: bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, bisphenol A novolac type epoxy resin, glycidyl ester type epoxy resin, aralkyl novolac type epoxy resin, biphenyl aralkyl type epoxy resin, naphthylene ether type epoxy resin, cresol novolac type epoxy resin, polyfunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene-based epoxy resins, naphthalene skeleton-modified novolac-based epoxy resins, phenol aralkyl-based epoxy resins, naphthol aralkyl-based epoxy resins, dicyclopentadiene-based epoxy resins, biphenyl-based epoxy resins, alicyclic epoxy resins, polyhydric alcohol-based epoxy resins, phosphorus-containing epoxy resins, compounds obtained by epoxidizing double bonds of glycidylamine, glycidyl ester, butadiene, and the like, and compounds obtained by reacting hydroxyl-containing silicone resins with epichlorohydrin. Among these, from the viewpoint of further improving flame retardancy and heat resistance, biphenyl aralkyl type epoxy resins, naphthylene ether type epoxy resins, polyfunctional phenol type epoxy resins, and naphthalene type epoxy resins are preferable, and biphenyl aralkyl type epoxy resins are more preferable.
The epoxy resin is preferably contained within a range not to impair the effects of the present invention. From the viewpoint of moldability and adhesion, the lower limit of the content of the epoxy resin is preferably 0.1 part by mass or more, more preferably 1 part by mass or more, and further preferably 2 parts by mass or more, when the total amount of the resin components in the resin composition is 100 parts by mass in the case where the epoxy resin is contained. The content of the epoxy resin is 0.1 part by mass or more, and the peel strength and toughness of the metal foil (copper foil) tend to be improved. When the epoxy resin is contained, the upper limit of the content of the epoxy resin is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, further preferably 20 parts by mass or less, further preferably 10 parts by mass or less, and further preferably 8 parts by mass or less, when the total amount of the resin components in the resin composition is 100 parts by mass. The content of the epoxy resin is 50 parts by mass or less, and thus the electrical characteristics tend to be improved.
The resin composition in the present embodiment may contain only 1 kind of epoxy resin, or may contain 2 or more kinds of epoxy resins. When 2 or more species are contained, the total amount is preferably within the above range.
The resin composition of the present embodiment may be substantially free of an epoxy resin. The substantial absence means that the content of the epoxy resin is less than 0.1 part by mass with respect to 100 parts by mass of the total amount of the resin components in the resin composition.
< < phenolic resin >)
The phenolic resin is not particularly limited as long as it is a compound or resin having 2 or more phenolic hydroxyl groups in 1 molecule.
Examples of the phenolic resin include: bisphenol a-type phenol resin, bisphenol E-type phenol resin, bisphenol F-type phenol resin, bisphenol S-type phenol resin, phenol novolac resin, bisphenol a novolac-type phenol resin, glycidyl ester-type phenol resin, aralkyl novolac phenol resin, biphenyl aralkyl-type phenol resin, cresol novolac phenol resin, polyfunctional phenol resin, naphthol novolac resin, polyfunctional naphthol resin, anthracene-type phenol resin, naphthalene skeleton-modified novolac phenol resin, phenol aralkyl phenol resin, naphthol aralkyl phenol resin, dicyclopentadiene-type phenol resin, biphenyl-type phenol resin, alicyclic phenol resin, polyhydric alcohol-type phenol resin, phosphorus-containing phenol resin, hydroxyl group-containing silicone resin, and the like. Among these, from the viewpoint of further improving the flame resistance, at least 1 selected from the group consisting of biphenyl aralkyl type phenol resins, naphthol aralkyl type phenol resins, phosphorus-containing phenol resins, and hydroxyl group-containing silicone resins is preferable.
The phenolic resin is preferably contained in a range not to impair the effects of the present invention. When the phenolic resin is contained, the content of the phenolic resin is preferably 0.1 part by mass or more and preferably 50 parts by mass or less, assuming that the total amount of the resin components in the resin composition is 100 parts by mass.
The resin composition in the present embodiment may contain only 1 kind of phenol resin, or may contain 2 or more kinds of phenol resins. When 2 or more species are contained, the total amount is preferably within the above range.
The resin composition of the present embodiment may be substantially free of a phenol resin. The substantially free means that the content of the phenolic resin is less than 0.1 part by mass relative to 100 parts by mass of the total amount of the resin components in the resin composition.
[ oxetane resin ]
The oxetane resin is not particularly limited as long as it is a compound having 2 or more oxetanyl groups.
Examples of the oxetane resin include oxetane, alkyl oxetane (e.g., 2-methyloxetane, 2-dimethyloxetane, 3-methyloxetane, 3-dimethyloxetane, etc.), 3-methyl-3-methoxymethyloxetane, 3-bis (trifluoromethyl) perfluorooxetane, 2-chloromethyloxetane, 3-bis (chloromethyl) oxetane, biphenyl-type oxetane, OXT-101 (product of Toyo Kabushiki Kaisha), and OXT-121 (product of Toyo Kabushiki Kaisha).
The oxetane resin is preferably contained within a range not to impair the effects of the present invention. The lower limit of the content of the oxetane resin is preferably 0.1 part by mass or more, more preferably 1 part by mass or more, and further preferably 2 parts by mass or more, when the oxetane resin is contained, assuming that the total amount of the resin components in the resin composition is 100 parts by mass. The content of the oxetane resin is 0.1 part by mass or more, and thus the peel strength and toughness of the metal foil (copper foil) tend to be improved. When the oxetane resin is contained, the upper limit of the content of the oxetane resin is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, further preferably 20 parts by mass or less, further preferably 10 parts by mass or less, and further preferably 8 parts by mass or less, when the total amount of the resin components in the resin composition is 100 parts by mass. When the content of the oxetane resin is 50 parts by mass or less, the electrical characteristics of the resin composition tend to be further improved.
The resin composition in the present embodiment may contain only 1 kind of oxetane resin, or may contain 2 or more kinds of oxetane resins. When 2 or more species are contained, the total amount is preferably within the above range.
The resin composition according to the present embodiment may have a structure substantially free of an oxetane resin. The substantial absence means that the content of the oxetane resin is less than 0.1 part by mass relative to 100 parts by mass of the total amount of the resin components in the resin composition.
< benzoxazine compound >)
The benzoxazine compound is not particularly limited as long as it has 2 or more dihydrobenzoxazine rings in 1 molecule.
Examples of the benzoxazine compound include bisphenol a type benzoxazine BA-BXZ (product of seiko chemical corporation), bisphenol F type benzoxazine BF-BXZ (product of seiko chemical corporation), and bisphenol S type benzoxazine BS-BXZ (product of seiko chemical corporation).
The benzoxazine compound is preferably contained in a range not to impair the effects of the present invention. The content of the benzoxazine compound is preferably 0.1 part by mass or more and preferably 50 parts by mass or less, when the total amount of the resin components in the resin composition is 100 parts by mass in the case of containing the benzoxazine compound.
The resin composition in the present embodiment may contain only 1 kind of benzoxazine compound, or may contain 2 or more kinds of benzoxazine compounds. When 2 or more species are contained, the total amount is preferably within the above range.
The resin composition of the present embodiment may have a structure substantially free of the benzoxazine compound. The substantial absence means that the content of the benzoxazine compound is less than 0.1 part by mass with respect to 100 parts by mass of the total amount of the resin components in the resin composition.
< Compound having polymerizable unsaturated group >)
The compound having a polymerizable unsaturated group is not particularly limited as long as it has 2 or more polymerizable unsaturated groups.
Examples of the compound having a polymerizable unsaturated group include: vinyl compounds (e.g., ethylene, propylene, styrene, divinylbenzene, divinylbiphenyl, etc.), acrylates (e.g., methyl (meth) acrylate, etc.), (meth) acrylates of monohydric or polyhydric alcohols (e.g., 2-hydroxypropyl (meth) acrylate, polypropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, etc.), epoxy (meth) acrylates (e.g., bisphenol a type epoxy (meth) acrylate, bisphenol F type epoxy (meth) acrylate, etc.), benzocyclobutene resins, etc.
The compound having an unsaturated group capable of polymerization is preferably contained within a range not to impair the effects of the present invention. The content of the compound having a polymerizable unsaturated group is preferably 0.1 part by mass or more and preferably 50 parts by mass or less, when the same compound is contained, assuming that the total amount of the resin components in the resin composition is 100 parts by mass.
The resin composition in the present embodiment may contain only 1 kind of compound having a polymerizable unsaturated group, or may contain 2 or more kinds of compounds having a polymerizable unsaturated group. When 2 or more species are contained, the total amount is preferably within the above range.
The resin composition according to the present embodiment may have a structure that does not substantially contain a compound having a polymerizable unsaturated group. The substantially free means that the content of the compound having a polymerizable unsaturated group is less than 0.1 part by mass with respect to 100 parts by mass of the total amount of the resin components in the resin composition.
Modified polyphenylene ether end-modified with substituent containing carbon-carbon unsaturated double bond (other than maleimide)
The modified polyphenylene ether end-modified with a substituent having a carbon-carbon unsaturated double bond (other than maleimide) is, for example, a modified polyphenylene ether in which all or a part of the end of the polyphenylene ether is end-modified with a substituent having a carbon-carbon unsaturated double bond. The substituent having a carbon-carbon unsaturated double bond is not particularly limited as long as it is a group other than a maleimide group, and examples thereof include an ethylenically unsaturated group. Examples of the ethylenically unsaturated group include an alkenyl group such as a vinyl group, an allyl group, an acryloyl group, a methacryloyl group, a propenyl group, a butenyl group, a hexenyl group, and an octenyl group, a cycloalkenyl group such as a cyclopentenyl group and a cyclohexenyl group, an alkenylaryl group such as a vinylbenzyl group and a vinylnaphthyl group, and a vinylbenzyl group is preferable. The term "polyphenylene ether" as used herein means a compound having a phenylene ether skeleton represented by the following formula (X1).
(in the formula (X1), R24、R25、R26And R27And optionally the same or different, represents an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom or a hydrogen atom. )
The modified polyphenylene ether may further contain a repeating unit represented by the formula (X2) and/or a repeating unit represented by the formula (X3).
(in the formula (X2), R28、R29、R30、R34、R35Optionally, the same or different, is an alkyl group having 6 or less carbon atoms or a phenyl group. R31、R32、R33Optionally the same or different, and is hydrogen atom, alkyl group with carbon number of 6 or less or phenyl group. )
(in the formula (X3), R36、R37、R38、R39、R40、R41、R42、R43Optionally the same or different, and is hydrogen atom, alkyl group with carbon number of 6 or less or phenyl group. -A-is a linear, branched or cyclic 2-valent hydrocarbon group having 20 or less carbon atoms. )
The modified polyphenylene ether may be one in which a part of the terminal is functionalized with a functional group such as an epoxy group, an amino group, a hydroxyl group, a mercapto group, a carboxyl group, or a silyl group. These can be used in 1 or 2 or more in combination.
The method for producing the modified polyphenylene ether is not particularly limited as long as the effects of the present invention can be obtained. For example, one functionalized with vinylbenzyl groups can be prepared as follows: the resin composition is produced by dissolving a 2-functional phenylene ether oligomer and vinylbenzyl chloride in a solvent, reacting the resulting solution with heating and stirring while adding a base, and then solidifying the resin. The functionalized carboxyl group can be produced as follows: for example, the functional group-functionalized derivative of an unsaturated carboxylic acid or its derivative is melt-kneaded with polyphenylene ether in the presence or absence of a radical initiator and reacted. Or may be made as follows: polyphenylene ether and unsaturated carboxylic acid, or a functional derivative thereof are dissolved in an organic solvent in the presence or absence of a radical initiator, and reacted in solution.
The modified polyphenylene ether preferably comprises a modified polyphenylene ether having an ethylenically unsaturated group at both ends (hereinafter, sometimes referred to as "modified polyphenylene ether (g)"). Examples of the ethylenically unsaturated group include an alkenyl group such as a vinyl group, an allyl group, an acryloyl group, a methacryloyl group, a propenyl group, a butenyl group, a hexenyl group, and an octenyl group, a cycloalkenyl group such as a cyclopentenyl group and a cyclohexenyl group, an alkenylaryl group such as a vinylbenzyl group and a vinylnaphthyl group, and a vinylbenzyl group is preferable. The two terminal 2 ethylenically unsaturated groups may be the same functional group or different functional groups.
The modified polyphenylene ether (G) having an ethylenically unsaturated group at the terminal (hereinafter may be simply referred to as modified polyphenylene ether (G)) has a structure shown in the formula (G1).
(in the formula (G1), X represents an aromatic group, (Y) m represents a polyphenylene ether moiety, and RG1、RG2、RG3Each independently represents a hydrogen atom, an alkyl group, an alkenyl group or an alkynyl group, m represents an integer of 1 to 100, n represents an integer of 1 to 6, and q represents an integer of 1 to 4. Preferably RG1、RG2、RG3Is a hydrogen atom. )
N is preferably an integer of 1 to 4, more preferably n is 1 or 2, and still more preferably n is 1. Further, q is preferably an integer of 1 to 3, more preferably q is 1 or 2, and still more preferably q is 2.
The modified polyphenylene ether (G) in the present embodiment is preferably represented by the formula (G2).
Here, - (O-X-O) -is preferably represented by the formula (G3) and/or the formula (G4).
(in the formula (G3), R4、R5、R6、R10、R11Optionally, the same or different, is an alkyl group having 6 or less carbon atoms or a phenyl group. R7、R8、R9Optionally the same or different, and is hydrogen atom, alkyl group with carbon number of 6 or less or phenyl group. )
(in the formula (G4), R12、R13、R14、R15、R16、R17、R18、R19Optionally the same as orDifferent from the above, the substituent is a hydrogen atom, an alkyl group having 6 or less carbon atoms or a phenyl group. -A-is a linear, branched or cyclic 2-valent hydrocarbon group having 20 or less carbon atoms. )
Further, - (Y-O) -is preferably represented by the formula (G5).
(in the formula (G5), R22And R23Optionally, the same or different, is an alkyl group having 6 or less carbon atoms or a phenyl group. R20And R21Optionally the same or different, and is hydrogen atom, alkyl group with carbon number of 6 or less or phenyl group. )
a. b represents an integer of 0 to 100, at least one of which is not 0. a. When b is an integer of 2 or more, it is possible to arrange- (Y-O) -a or- (Y-O) -b in the structure represented by the formula (G5) of 1 kind, or in the structure represented by the formula (G5) of 2 or more kinds at random.
Examples of-A-in the formula (G4) include, but are not limited to, 2-valent organic groups such as methylene, ethylidene, 1-methylethylidene, 1-propylidene, 1, 4-phenylenebis (1-methylethylidene), 1, 3-phenylenebis (1-methylethylidene), cyclohexylidene, phenylmethylene, naphthylmethylene, and 1-phenylethynyl.
Among the modified polyphenylene ethers (g), R is preferred4、R5、R6、R10、R11、R20、R21Is C3 or lower alkyl, R7、R8、R9、R12、R13、R14、R15、R16、R17、R18、R19、R22、R23The polyphenylene ether is a polyphenylene ether having a hydrogen atom or an alkyl group having 3 or less carbon atoms, and particularly preferably a polyphenylene ether in which- (O-X-O) -represented by the formula (G3) or the formula (G4) is represented by the formula (9), the formula (10), and/or the formula (11) or the formula (G5) is represented by the formula (12) or the formula (13). a. When b is an integer of 2 or more, - (Y-O) -a or- (Y-O) -b is preferably a structure in which the formulas (12) and (13) are arranged, or a structure in which the formulas (12) and (13) are arranged randomly.
(in the formula (10), R44、R45、R46、R47Optionally identical or different, is a hydrogen atom or a methyl group. -B-is a linear, branched or cyclic 2-valent hydrocarbon group having 20 or less carbon atoms. )
Examples of-B-include those similar to the examples of-A-in the formula (G4).
(in the formula (11), -B-is a linear, branched or cyclic 2-valent hydrocarbon group having 20 or less carbon atoms.)
Examples of-B-include those similar to the examples of-A-in the formula (G4).
The number average molecular weight of the modified polyphenylene ether in terms of polystyrene by GPC is preferably 500 or more and 3000 or less. When the number average molecular weight is 500 or more, the stickiness tends to be further suppressed when the resin composition of the present embodiment is formed into a coating film. The solubility in a solvent tends to be further improved by a number average molecular weight of 3000 or less.
The modified polyphenylene ether preferably has a weight average molecular weight in terms of polystyrene by GPC of 800 or more and 10000 or less, more preferably 800 or more and 5000 or less. When the lower limit value is not less than the above-mentioned lower limit value, the dielectric constant and the dielectric loss tangent tend to be lower, and when the upper limit value is not more than the above-mentioned upper limit value, the solubility in a solvent, the low viscosity, and the moldability tend to be further improved.
Further, the equivalent weight of the carbon-carbon unsaturated double bond at the terminal of the modified polyphenylene ether is preferably 400 to 5000g, more preferably 400 to 2500g, per 1 carbon-carbon unsaturated double bond. When the dielectric constant is not less than the lower limit, the dielectric constant and the dielectric loss tangent tend to be lower. When the content is not more than the above upper limit, the solubility in a solvent, the low viscosity, and the moldability tend to be further improved.
The method for producing the modified polyphenylene ether represented by the formula (2) in the present embodiment is not particularly limited, and can be produced, for example, by the following steps: a step (oxidative coupling step) of oxidatively coupling a 2-functional phenol compound and a 1-functional phenol compound to obtain a 2-functional phenylene ether oligomer; and a step (vinylbenzyl etherification step) of vinylbenzyl etherification of the terminal phenolic hydroxyl group of the obtained 2-functional phenylene ether oligomer. As such a modified polyphenylene ether, for example, Mitsubishi gas chemical (OPE-2St1200, etc.) can be used.
In the oxidative coupling step, for example, the 2-functional phenol compound, the 1-functional phenol compound and the catalyst are dissolved in a solvent, and oxygen is blown under heating and stirring to obtain the 2-functional phenylene ether oligomer. The 2-functional phenol compound is not particularly limited, and examples thereof include at least 1 selected from the group consisting of 2,2 ', 3,3 ', 5,5 ' -hexamethyl- (1,1 ' -biphenol) -4,4 ' -diol, 4 ' -methylenebis (2, 6-dimethylphenol), 4 ' -dihydroxyphenylmethane, and 4,4 ' -dihydroxy-2, 2 ' -diphenylpropane. The 1-functional phenol compound is not particularly limited, and examples thereof include 2, 6-dimethylphenol and/or 2,3, 6-trimethylphenol. The catalyst is not particularly limited, and examples thereof include copper salts (e.g., CuCl, CuBr, CuI, CuCl)2、CuBr2Etc.), amines (e.g., di-N-butylamine, N-butyldimethylamine, N '-di-t-butylethylenediamine, pyridine, N' -tetramethylethylenediamine, piperidine, imidazole, etc.), etc. The solvent is not particularly limited, and examples thereof include at least 1 selected from the group consisting of toluene, methanol, methyl ethyl ketone, and xylene.
In the vinylbenzyl etherification step, for example, it can be produced as follows: the 2-functional phenylene ether oligomer obtained by the oxidative coupling step and vinylbenzyl chloride are dissolved in a solvent, and a base is added thereto under heating and stirring to cause a reaction, and then the resin is solidified. The vinylbenzyl chloride is not particularly limited, and examples thereof include at least 1 selected from the group consisting of o-vinylbenzyl chloride, m-vinylbenzyl chloride and p-vinylbenzyl chloride. The base is not particularly limited, and examples thereof include at least 1 selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium methoxide, and sodium ethoxide. In the vinylbenzyl etherification step, an acid may be used to neutralize the base remaining after the reaction, and the acid is not particularly limited, and examples thereof include at least 1 selected from the group consisting of hydrochloric acid, sulfuric acid, phosphoric acid, boric acid, and nitric acid. The solvent is not particularly limited, and examples thereof include at least 1 selected from the group consisting of toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethylformamide, dimethylacetamide, dichloromethane, and chloroform. Examples of the method for solidifying the resin include: a method of evaporating and drying the solvent, a method of mixing the reaction solution with a poor solvent and reprecipitating, and the like.
The lower limit of the content of the modified polyphenylene ether is preferably 1 part by mass or more, more preferably 5 parts by mass or more, further preferably 10 parts by mass or more, further preferably 15 parts by mass or more, further preferably 20 parts by mass or more, and further preferably 25 parts by mass or more, when the total amount of the resin components in the resin composition is 100 parts by mass in the case of containing the modified polyphenylene ether. The upper limit of the content of the modified polyphenylene ether is preferably 90 parts by mass or less, more preferably 85 parts by mass or less, further preferably 70 parts by mass or less, and further preferably 60 parts by mass or less, when the total amount of the resin components in the resin composition is 100 parts by mass in the case of containing the modified polyphenylene ether. When the content of the modified polyphenylene ether is in the above range, the low dielectric loss tangent and the reactivity tend to be further improved.
The resin composition in the present embodiment may contain only 1 kind of modified polyphenylene ether, or may contain 2 or more kinds of modified polyphenylene ethers. When 2 or more species are contained, the total amount is preferably within the above range.
< elastomer >
The elastomer is not particularly limited, and a known elastomer can be widely used.
Examples of the elastomer include: at least 1 selected from the group consisting of polyisoprene, polybutadiene, styrene butadiene, butyl rubber, ethylene propylene rubber, styrene butadiene ethylene, styrene butadiene styrene, styrene isoprene styrene, styrene ethylene butylene styrene, styrene propylene styrene, styrene ethylene propylene styrene, fluororubber, silicone rubber, hydrogenated compounds thereof, alkyl compounds thereof, and copolymers thereof. Among these, from the viewpoint of excellent electrical characteristics, at least 1 selected from the group consisting of styrene butadiene, styrene butadiene ethylene, styrene butadiene styrene, styrene isoprene styrene, styrene ethylene butylene styrene, styrene propylene styrene, styrene ethylene propylene styrene, hydrogenated compounds thereof, alkyl compounds thereof, and copolymers thereof is preferable, and from the viewpoint of further excellent compatibility with the modified polyphenylene ether, at least 1 selected from the group consisting of styrene butadiene rubber, and isoprene rubber is more preferable.
The elastomer in the present embodiment preferably has an SP value of 9 (cal/cm) from the viewpoint of excellent electrical characteristics3)1/2The following. The SP value is called the dissolution parameter and is therefore defined by 1cm3Square root of heat of vaporization (cal/cm) required for vaporization of a liquid3)1/2And (4) calculating. In general, the smaller the value, the lower the polarity, the closer the values, the higher the affinity between the 2 components, and the SP value of the elastomer is 9 (cal/cm)3)1/2In the following, the electrical characteristics of the resin composition used for the printed wiring board more suitable for high frequency applications can be obtained.
The elastomer in the present embodiment is preferably used for a material for a printed wiring board (for example, a laminated plate or a metal foil-clad laminated plate) or the like because the crack resistance is further improved if the elastomer has a weight average molecular weight of 80000 or more in terms of polystyrene by GPC method and is solid at 25 ℃. On the other hand, if the weight average molecular weight in terms of polystyrene based on the GPC method is 40000 or less and is liquid at 25 ℃, warpage when the film is applied to a substrate is reduced, and therefore, the film is particularly suitable as a laminate material for a printed wiring board.
The elastomer is preferably contained within a range not to impair the effects of the present invention. The lower limit of the content of the elastomer is preferably 1 part by mass or more, more preferably 3 parts by mass or more, and further preferably 5 parts by mass or more, based on 100 parts by mass of the total amount of the resin components in the resin composition, when the elastomer is contained. When the content of the elastomer is 5 parts by mass or more, the electrical characteristics tend to be further improved. When the elastomer is contained, the upper limit of the content of the elastomer is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, further preferably 70 parts by mass or less, further preferably 60 parts by mass or less, and further preferably 50 parts by mass or less, based on 100 parts by mass of the total amount of the resin components in the resin composition. When the content of the elastomer is 20 parts by mass or less, the flame resistance tends to be improved.
The resin composition in the present embodiment may contain only 1 kind of elastomer, or may contain 2 or more kinds of elastomers. When 2 or more species are contained, the total amount is preferably within the above range.
The resin composition in the present embodiment may be configured to contain substantially no elastomer. The substantially free means that the content of the elastomer is less than 1 part by mass with respect to 100 parts by mass of the total amount of the resin components in the resin composition.
Active ester compound
The active ester compound is not particularly limited, and examples thereof include compounds having 2 or more active ester groups in 1 molecule.
The active ester compound may be a linear, branched or cyclic compound. Among these, from the viewpoint of further improving heat resistance, an active ester compound obtained by reacting a carboxylic acid compound and/or a thiocarboxylic acid compound with a hydroxyl compound and/or a thiol compound is preferable, an active ester compound obtained by reacting a carboxylic acid compound with 1 or more compounds selected from the group consisting of a phenol compound, a naphthol compound and a thiol compound is more preferable, an aromatic compound having 2 or more active ester groups in 1 molecule obtained by reacting a carboxylic acid compound with an aromatic compound having a phenolic hydroxyl group is further preferable, and an aromatic compound having 2 or more active ester groups in 1 molecule obtained by reacting a compound having 2 or more carboxylic acids in 1 molecule with an aromatic compound having a phenolic hydroxyl group is particularly preferable. The carboxylic acid compound includes 1 or more selected from the group consisting of benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid, and among these, from the viewpoint of further improving the heat resistance, 1 or more selected from the group consisting of succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, and terephthalic acid is preferable, and 1 or more selected from the group consisting of isophthalic acid and terephthalic acid is more preferable. Examples of the thiocarboxylic acid compound include 1 or more selected from the group consisting of thioacetic acid and thiobenzoic acid. The phenol compound or naphthol compound may include 1 or more selected from the group consisting of hydroquinone, resorcinol, bisphenol a, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol a, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α -naphthol, β -naphthol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, benzenetriol, dicyclopentadienyl diphenol and phenol novolac, and bisphenol a, bisphenol F, bisphenol S, methylated bisphenol a, methylated bisphenol F, methylated bisphenol S, catechol, α -naphthol, and phenol novolac are preferable from the viewpoint of further improving heat resistance and solvent solubility, Beta-naphthol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, benzenetriol, dicyclopentadienyl diphenol, phenol novolak, more preferably 1 or more selected from the group consisting of catechol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, benzenetriol, dicyclopentadienyl diphenol and phenol novolak, still more preferably 1 or more selected from the group consisting of 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, and phenol novolak, 1 or more of dicyclopentadienyl diphenol and phenol novolac, and particularly preferably 1 or more of dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, dicyclopentadienyl diphenol and phenol novolac (preferably 1 or more of dicyclopentadienyl diphenol selected from the group consisting of dicyclopentadienyl diphenol and phenol novolac, and more preferably dicyclopentadienyl diphenol). The thiol compound includes 1 or more selected from the group consisting of benzenedithiol and triazine dithiol. The active ester compound is preferably a compound having 2 or more carboxylic acids in 1 molecule and containing an aliphatic chain from the viewpoint of further improving the compatibility with the epoxy resin, and is preferably a compound having an aromatic ring from the viewpoint of further improving the heat resistance. More specific examples of the active ester compound include those described in Japanese patent application laid-open No. 2004-277460.
The active ester compound may be a commercially available product or may be prepared by a known method. Examples of commercially available products include: compounds having a dicyclopentadienyl diphenol structure (for example, EXB9451, EXB9460S, HPC-8000-65T (all available from DIC corporation), etc.), acetylates of phenol novolacs (for example, DC808 (available from mitsubishi chemical corporation)), and benzoylates of phenol novolacs (for example, YLH1026, YLH1030, YLH1048 (all available from mitsubishi chemical corporation)). EXB9460S is preferable from the viewpoint of further improving the storage stability of the varnish and reducing the thermal expansion coefficient of the cured product.
The method for producing the active ester compound can be carried out by a known method, and for example, can be obtained by a condensation reaction of a carboxylic acid compound and a hydroxyl compound. Specific examples thereof include the following methods: the carboxylic acid compound or the acid halide thereof (a), the hydroxyl compound (b), and the aromatic monohydroxy compound (c) are reacted in a ratio of 0.05 to 0.75 mol of the phenolic hydroxyl group (b) and 0.25 to 0.95 mol of the aromatic monohydroxy compound (c) to 1mol of the carboxyl group or the acid halide group (a).
The active ester compound is preferably contained in a range not to impair the effects of the present invention. When the active ester compound is contained, the content of the active ester compound is preferably 1 part by mass or more, and preferably 90 parts by mass or less, relative to 100 parts by mass of the total amount of the resin components in the resin composition.
The resin composition in the present embodiment may contain only 1 kind of active ester compound, or may contain 2 or more kinds of active ester compounds. When 2 or more species are contained, the total amount is preferably within the above range.
The resin composition of the present embodiment may be configured to contain substantially no active ester compound. The substantial absence means that the content of the active ester compound is less than 1 part by mass relative to 100 parts by mass of the total amount of the resin components in the resin composition.
In the case where the resin composition of the present embodiment does not contain the filler (C) described later or does not substantially contain the filler (C) described later, the total amount of the resin components is preferably 70% by mass or more, more preferably 80% by mass or more, and further preferably 90% by mass or more of the components other than the solvent of the resin composition.
When the resin composition in the present embodiment contains the filler (C) described later, the total amount of the resin components is preferably 30% by mass or more, preferably 35% by mass or more, and more preferably 40% by mass or more of the components other than the solvent in the resin composition. The upper limit is preferably 70% by mass or less, more preferably 65% by mass or less, and still more preferably 60% by mass or less.
In any of the above cases, it is preferable that 90% by mass or more of the resin component is composed of the cyanate ester compound (a), the bismaleimide compound (B) represented by the formula (1), and another maleimide compound.
< Filler (C) >
The resin composition of the present embodiment preferably contains a filler (C) for the purpose of low dielectric constant, low dielectric loss tangent, improved flame resistance and low thermal expansion. As the filler (C) used in the present embodiment, known ones can be suitably used, and the kind thereof is not particularly limited, and those generally used in the art can be suitably used. Specifically, there may be mentioned: silica materials such as natural silica, fused silica, synthetic silica, amorphous silica, Aerosil and hollow silica, white carbon, titanium white, zinc oxide, magnesium oxide, zirconium oxide, boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, barium sulfate, aluminum hydroxide and aluminum hydroxide heat-treated products (those obtained by heat-treating aluminum hydroxide to reduce a part of crystal water), metal hydrates such as boehmite and magnesium hydroxide, molybdenum compounds such as molybdenum oxide and zinc molybdate, zinc borate, zinc stannate, aluminum oxide, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, and glass short fibers (including E-glass, Glass fine particles such as T glass, D glass, S glass, and Q glass), and inorganic fillers such as hollow glass and spherical glass; and organic fillers such as styrene-type, butadiene-type, and acrylic-type rubber powders, core-shell-type rubber powders, silicone resin powders, silicone rubber powders, and silicone composite powders.
Among these, 1 or 2 or more selected from the group consisting of silica, aluminum hydroxide, boehmite, magnesium oxide and magnesium hydroxide are suitable, and silica is more preferred. The silica is preferably spherical silica. The spherical silica may be hollow silica.
By using these fillers (C), the resin composition has improved properties such as thermal expansion properties, dimensional stability, and flame retardancy.
The content of the filler (C) in the resin composition of the present embodiment may be appropriately set according to the desired characteristics, and is not particularly limited, and when the total amount of the resin components in the resin composition is 100 parts by mass, it is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, further preferably 30 parts by mass or more, further preferably 50 parts by mass or more, and further preferably 75 parts by mass or more. The upper limit is preferably 1600 parts by mass or less, more preferably 1200 parts by mass or less, further preferably 1000 parts by mass or less, further preferably 750 parts by mass or less, further preferably 500 parts by mass or less, further preferably 300 parts by mass or less, further preferably 250 parts by mass or less, and may be 200 parts by mass or less.
The resin composition in the present embodiment may contain only 1 kind of filler (C), or may contain 2 or more kinds of fillers (C). When 2 or more species are contained, the total amount is preferably within the above range.
On the other hand, in the present embodiment, the resin composition may be configured to substantially not contain the filler (C). The substantial absence means that the content of the filler (C) is less than 1% by mass, preferably 0.1% by mass or less, of the content of the resin component.
When the filler (C) is used here, it is preferable to use a silane coupling agent and/or a wetting dispersant in combination. The silane coupling agent is preferably used for surface treatment of inorganic substances, and the kind thereof is not particularly limited. Specifically, there may be mentioned: and aminosilane-based compounds such as γ -aminopropyltriethoxysilane and N- β - (aminoethyl) - γ -aminopropyltrimethoxysilane, alkoxysilane-based compounds such as γ -glycidoxypropyltrimethoxysilane and β - (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, vinylsilane-based compounds such as γ -methacryloxypropyltrimethoxysilane and vinyl-tris (β -methoxyethoxy) silane, cationic silane-based compounds such as N- β - (N-vinylbenzylaminoethyl) - γ -aminopropyltrimethoxysilane hydrochloride, and phenylsilane-based compounds. The silane coupling agent may be used alone, or 2 or more kinds may be used in combination. The wetting dispersant may be used suitably for general coating materials, and the type thereof is not particularly limited. The copolymer-based wetting dispersant is preferably used, and specific examples thereof include Disperbyk-110, 111, 161, 180, 2009, 2152, BYK-W996, BYK-W9010, BYK-W903, BYK-W940 and the like manufactured by BYK Chemie Japan. The wetting dispersant may be used alone, or 2 or more kinds thereof may be used in combination.
The content of the silane coupling agent is not particularly limited, and may be about 1 to 5 parts by mass relative to 100 parts by mass of the total amount of the resin components in the resin composition. The content of the dispersant (particularly, a wetting dispersant) is not particularly limited, and may be, for example, about 0.5 to 5 parts by mass relative to 100 parts by mass of the total amount of the resin components in the resin composition.
< curing accelerator >
The resin composition of the present embodiment may further include a curing accelerator. The curing accelerator is not particularly limited, and examples thereof include: imidazoles such as triphenylimidazole; organic peroxides such as benzoyl peroxide, lauroyl peroxide, acetyl peroxide, p-chlorobenzoyl peroxide, and di-t-butyl peroxyphthalate; azo compounds such as azodinitrile; tertiary amines such as N, N-dimethylbenzylamine, N-dimethylaniline, N-dimethyltoluidine, 2-N-ethylanilinoethanol, tri-N-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutanediamine, and N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcinol, catechol, and the like; organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octylate, manganese octylate, tin oleate, dibutyltin maleate, manganese naphthenate, cobalt naphthenate, and iron acetylacetonate; those obtained by dissolving these organic metal salts in a hydroxyl group-containing compound such as phenol or bisphenol; inorganic metal salts such as tin chloride, zinc chloride and aluminum chloride; organotin compounds such as dioctyltin oxide, other alkyltin and alkyltin oxide; and the like.
Preferred curing accelerators are imidazoles and organometallic salts, more preferably used in combination with both imidazoles and organometallic salts.
When the curing accelerator is contained, the lower limit value is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, and further preferably 0.1 parts by mass or more, based on 100 parts by mass of the total amount of the resin components in the resin composition. The upper limit of the content of the curing accelerator is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and still more preferably 2 parts by mass or less, based on 100 parts by mass of the total amount of the resin components in the resin composition.
The curing accelerator may be used alone in 1 kind, or in combination of 2 or more kinds. When 2 or more kinds are used, the total amount is in the above range.
< solvent >
The resin composition of the present embodiment may contain a solvent, and preferably contains an organic solvent. In the above case, the resin composition of the present embodiment is a form (solution or varnish) in which at least a part, preferably all, of the various resin components are dissolved or compatible in a solvent. The solvent is not particularly limited as long as it is a polar organic solvent or a nonpolar organic solvent that can dissolve or dissolve at least a part of, preferably all, the various resin components, and examples of the polar organic solvent include ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), cellosolves (e.g., propylene glycol monomethyl ether acetate, etc.), esters (e.g., ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.) amides (e.g., dimethoxyacetamide, dimethylformamides, etc.), and examples of the nonpolar organic solvent include aromatic hydrocarbons (e.g., toluene, xylene, etc.).
When the resin composition of the present embodiment contains a solvent, the content thereof is not particularly limited, and may be, for example, 1 mass% or more, 10 mass% or more, 30 mass% or more, or 40 mass% or more of the resin composition. The upper limit may be 99 mass% or less, 80 mass% or less, or 70 mass% or less, or 60 mass% or less.
The solvent may be used alone in 1 kind, or in combination of 2 or more kinds. When 2 or more kinds are used, the total amount is in the above range.
The resin composition of the present embodiment preferably has a solid content of 10 mass% or more, more preferably 15 mass% or more, further preferably 20 mass% or more, further preferably 30 mass% or more, and may be 40 mass% or more and 50 mass% or more in the resin composition. The upper limit of the amount of the solid component is preferably 90% by mass or less, more preferably 80% by mass or less, further preferably 70% by mass or less, and may be 60% by mass or less.
The solid content means a component other than the solvent in the resin composition.
< other ingredients >
The resin composition of the present embodiment may contain various polymer compounds such as thermoplastic resins and oligomers thereof, and various additives in addition to the above components within a range not to impair the effects of the present invention. Examples of the additives include flame retardants, ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, flow control agents, lubricants, antifoaming agents, dispersants, leveling agents, gloss agents, and polymerization inhibitors. These additives may be used alone in 1 kind, or in combination of 2 or more kinds.
The resin composition of the present embodiment may be configured to contain substantially no flame retardant. The substantially free means that the content of the flame retardant is less than 0.01 part by mass, preferably 0 part by mass, relative to 100 parts by mass of the total amount of the resin composition. The resin composition of the present embodiment is valuable in that high flame retardancy can be maintained even when the composition is formed so as not to substantially contain a flame retardant. Specifically, the resin composition of the present embodiment can make the flame retardancy of a material (printed circuit board or the like) molded to a thickness of 0.8mm (further 0.4mm) in the UL (Underwriters Laboratories Inc.) standard V-0. Flame retardancy was measured according to the description of examples described later.
< embodiment of the resin composition >
Hereinafter, a more specific embodiment of the present embodiment will be described. The present embodiment is not limited to these.
A first specific example of the resin composition of the present embodiment is an embodiment in which the solid content in the resin composition contains 90 mass% or more (preferably 95 mass% or more) of the resin component. In the present embodiment, the resin component preferably contains a cyanate ester compound (a), a bismaleimide compound (B) represented by formula (1), and another maleimide compound.
The resin composition of the first embodiment can be used to form a test piece having a thickness of 0.8mm, and the dielectric constant (Dk) at 10GHz can be 3.0 or less, or can be 2.8 or less. The lower limit of the dielectric constant is preferably 0, but it is practically 2.0 or more. The resin composition of the first embodiment may have a dielectric loss tangent (Df) at 10GHz of a test piece molded to a thickness of 0.8mm of 0.0050 or less, or may have a dielectric loss tangent (Df) of less than 0.0045, or may have a dielectric loss tangent of 0.0044 or less. The lower limit of the dielectric constant is preferably 0, and is practically 0.0020 or more. The dielectric constant and the dielectric loss tangent were measured by the methods described in the examples described below.
The resin composition of the first embodiment may have a 1% mass reduction temperature of a test piece molded to a thickness of 0.8mm of 370 ℃ or higher, or 380 ℃ or higher. The upper limit of the 1% mass reduction temperature is not particularly limited, and it is practical that the temperature is 420 ℃ or lower.
The resin composition of the first embodiment can be used to form a test piece having a thickness of 0.8mm, and the mass loss rate at 450 ℃ can be 19.0% or less, or 18.0% or less. The lower limit of the mass reduction rate at 450 ℃ is preferably 0%, and it is practical that the lower limit is 10% or more.
The second specific example of the resin composition of the present embodiment is an embodiment in which the solid content in the resin composition contains 5 to 70 mass% (preferably 20 to 60 mass%) of the resin component and 95 to 30 mass% (preferably 80 to 40 mass%) of the filler. In the present embodiment, the resin component preferably contains a cyanate ester compound (a), a bismaleimide compound (B) represented by formula (1), and another maleimide compound. The filler material is preferably spherical silica.
< method for producing resin composition >
The method for producing a resin composition of the present embodiment is a method for producing a resin composition containing a cyanate ester compound (a) and a bismaleimide compound (B) represented by formula (1), and the method for producing the resin composition includes the steps of: a cyanate ester compound (A) and a bismaleimide compound (B) are mixed with a solvent, and the content of the bismaleimide compound (B) is 0.1 to 30 mass% (preferably 0.1 to 20 mass%) of the resin composition.
By setting the content of the bismaleimide compound (B) in the above range, the compound can be appropriately dissolved in a solvent, and the appearance of a varnish and the appearance of a prepreg can be further improved. In particular, by using the bismaleimide compound represented by the above formula (1-2) as the bismaleimide compound represented by the formula (1), the appearance can be further improved.
Further, the method for producing a resin composition according to the present embodiment preferably further contains 1 or more selected from the group consisting of a maleimide compound other than the bismaleimide compound (B), an epoxy resin, a phenol resin, an oxetane resin, a benzoxazine compound, a compound having a polymerizable unsaturated group, a modified polyphenylene ether having a terminal-modified substituent containing a carbon-carbon unsaturated double bond (other than maleimide), an elastomer, and an active ester compound, and more preferably further contains 1 or more selected from the group consisting of a maleimide compound other than the bismaleimide compound (B), an epoxy resin, a phenol resin, an oxetane resin, a benzoxazine compound, and a compound having a polymerizable unsaturated group. By blending such other resin components, the appearance can be further improved and other properties can be further improved.
< usage >)
The resin composition of the present embodiment is used as a cured product. Specifically, the resin composition of the present embodiment can be suitably used as a low dielectric constant material and/or a low dielectric loss tangent material, and can be suitably used as an insulating layer of a printed wiring board or a material for a semiconductor package. The resin composition of the present embodiment can be suitably used as a prepreg, a metal foil-clad laminate using the prepreg, a resin sheet, and a material constituting a printed wiring board.
The resin composition of the present embodiment is used as a material for a layered (including a film-like and sheet-like) molded article such as an insulating layer of a printed wiring board, a prepreg, and a resin sheet, and when the layered molded article is formed, the thickness thereof is preferably 5 μm or more, more preferably 10 μm or more. The upper limit of the thickness of the molded article is preferably 200 μm or less, more preferably 180 μm or less. For example, when a substrate such as a glass cloth is impregnated with the resin composition of the present embodiment, the thickness of the layered molded article is a thickness including the substrate.
The material formed from the resin composition of the present embodiment can be used for the purpose of forming a pattern by exposure and development, and can also be used for the purpose of not performing exposure and development. It is particularly suitable for the use without exposure development.
< prepreg >)
The prepreg of the present embodiment is formed of a substrate (prepreg substrate) and the resin composition of the present embodiment. The prepreg of the present embodiment can be obtained, for example, as follows: the resin composition of the present embodiment is obtained by applying (for example, impregnating or coating) the resin composition to a base material, and then semi-curing the base material by heating (for example, a method of drying the base material at 120 to 220 ℃ for 2 to 15 minutes). In the above case, the amount of the resin composition (including the cured product of the resin composition) adhering to the base material, that is, the amount of the resin composition (including the filler) relative to the total amount of the prepreg after semi-curing is preferably in the range of 20 to 99 mass%.
The base material is not particularly limited as long as it is a base material for various printed wiring board materials. Examples of the material of the substrate include inorganic fibers (e.g., Quartz) other than glass fibers (e.g., E glass, D glass, L glass, S glass, T glass, Q glass, UN glass, NE glass, and spherical glass), and organic fibers (e.g., polyimide, polyamide, polyester, and liquid crystal polyester). Examples of the base material include, but are not particularly limited to, base materials made of layered fibers such as woven fabric, nonwoven fabric, roving, chopped strand mat, and surfingmat. In particular, a base material made of long fibers such as glass cloth is preferable. The long fibers herein mean, for example, ones having a number average fiber length of 6mm or more. These substrates may be used alone in 1 kind, or in combination of 2 or more kinds. Among these substrates, woven fabrics subjected to a super-splitting treatment and a blocking treatment are preferable from the viewpoint of dimensional stability, glass woven fabrics subjected to a surface treatment with a silane coupling agent such as an epoxy silane treatment and an aminosilane treatment are preferable from the viewpoint of moisture absorption and heat resistance, and low-dielectric glass cloths formed of glass fibers exhibiting low dielectric constant and low dielectric loss tangent such as L-glass, NE-glass, and Q-glass are preferable from the viewpoint of electrical characteristics. The thickness of the substrate is not particularly limited, and may be, for example, about 0.01 to 0.19 mm.
Metal foil clad laminate
The metal foil-clad laminate of the present embodiment includes: a layer formed of at least 1 sheet of the prepreg of the present embodiment; and a metal foil disposed on one or both surfaces of the layer formed of the prepreg. The metal foil-clad laminate of the present embodiment can be produced, for example, by the following method: at least 1 prepreg of the present embodiment is arranged (preferably, 2 or more prepregs are stacked), and a metal foil is arranged on one surface or both surfaces thereof, followed by lamination molding. More specifically, the prepreg can be produced by arranging a metal foil of copper, aluminum, or the like on one surface or both surfaces of the prepreg and laminating the metal foil. The number of the prepreg is preferably 1 to 10, more preferably 2 to 10, and further preferably 2 to 7. The metal foil is not particularly limited as long as it is used for a material for a printed wiring board, and examples thereof include a copper foil such as a rolled copper foil and an electrolytic copper foil. The thickness of the metal foil (copper foil) is not particularly limited, and may be 1.5 μm or more, and further may be about 2 to 70 μm. Examples of the molding method include a method generally used for molding a laminate plate or a multilayer plate for a printed wiring board, and more specifically, the following methods: using a multi-stage press, a multi-stage vacuum press, a continuous forming machine, an autoclave forming machine, etc., at a temperature of about 180-350 ℃, a heating time of about 100-300 minutes, a surface pressure of 20 ℃100kg/cm2And performing left-right lower lamination molding. Further, a multilayer board can also be formed by combining the prepreg of the present embodiment with a separately produced wiring board for an inner layer (also referred to as an inner layer circuit board) and laminating and molding the same. As a method for producing a multilayer board, for example, a multilayer board can be produced by arranging metal foils (copper foils) of about 35 μm on both surfaces of 1 prepreg of the present embodiment, laminating the prepregs by the above-described molding method to form an inner layer circuit, blackening the circuit to form an inner layer circuit board, alternately arranging 1 prepreg of the present embodiment and the inner layer circuit board, further arranging a metal foil (copper foil) on the outermost layer, and laminating and molding the prepregs under the above-described conditions, preferably under vacuum. The metal foil-clad laminate of the present embodiment can be suitably used as a printed wiring board.
< < printed circuit board >)
The printed wiring board of the present embodiment is a printed wiring board including an insulating layer and a conductor layer disposed on a surface of the insulating layer, the insulating layer including: at least one of a layer formed from the resin composition of the present embodiment and a layer formed from the prepreg of the present embodiment. Such a printed circuit board can be manufactured according to a conventional method, and the manufacturing method thereof is not particularly limited. An example of a method for manufacturing a printed wiring board is described below. First, a metal-clad laminate such as the copper-clad laminate is prepared. Next, the surface of the metal foil-clad laminate was subjected to etching treatment to form an inner layer circuit, thereby producing an inner layer substrate. The surface of the inner layer circuit of the inner layer substrate is subjected to surface treatment for improving the adhesive strength as required, and then a required number of prepregs are stacked on the surface of the inner layer circuit, and further a metal foil for an outer layer circuit is stacked on the outer side of the prepregs, and the prepregs are integrally molded by heating and pressing. In this manner, a multilayer laminated board in which a base material and an insulating layer formed of a cured product of a thermosetting resin composition are formed between metal foils for an inner layer circuit and an outer layer circuit is manufactured. Then, the multilayer laminated board is subjected to opening processing for a through hole or a via hole, a plating metal coating film for conducting the metal foil for the inner layer circuit and the metal foil for the outer layer circuit is formed on the wall surface of the hole, and the metal foil for the outer layer circuit is further subjected to etching treatment to form the outer layer circuit, thereby manufacturing a printed wiring board.
The printed wiring board obtained in the above manufacturing example has an insulating layer; and a conductor layer formed on a surface of the insulating layer, wherein the insulating layer has a structure including the resin composition of the present embodiment. That is, the prepreg of the present embodiment (for example, a prepreg formed of a base material and the resin composition of the present embodiment impregnated or applied thereto) and the layer formed of the resin composition in the metal foil-clad laminate of the present embodiment serve as the insulating layer of the present embodiment.
< < resin sheet >
The resin sheet of the present embodiment includes: a support body; and a layer formed of the resin composition of the present embodiment disposed on the surface of the support. The resin sheet can be used as a film for lamination or a dry film solder resist. The method for producing the resin sheet is not particularly limited, and examples thereof include the following: a resin sheet is obtained by applying (coating) a solution in which the resin composition of the present embodiment is dissolved in a solvent to a support and drying the applied solution.
Examples of the support used herein include: the support is not particularly limited, and examples thereof include polyethylene films, polypropylene films, polycarbonate films, polyethylene terephthalate films, ethylene tetrafluoroethylene copolymer films, release films having a release agent applied to the surface of these films, organic film substrates such as polyimide films, conductor foils such as copper foils and aluminum foils, and plate-like supports such as glass plates, SUS plates, and FRPs.
Examples of the coating method (coating method) include the following methods: the solution in which the resin composition of the present embodiment is dissolved in a solvent is applied to a support by a bar coater, a die coater, a doctor blade, a baking applicator, or the like. After drying, the support may be peeled from the resin sheet in which the support and the resin composition are laminated or etched to form a single-layer sheet. The resin composition of the present embodiment is dissolved in a solvent, and the solution is supplied into a mold having a sheet-like cavity, dried, and molded into a sheet-like shape.
In the production of the single-layer sheet or the resin sheet according to the present embodiment, the drying conditions for removing the solvent are not particularly limited, and the solvent is likely to remain in the resin composition at a low temperature, and the resin composition is cured at a high temperature, and therefore, the temperature is preferably from 20 to 200 ℃ for 1 to 90 minutes. In the single-layer sheet or the resin sheet, the resin composition may be used in an uncured state in which only the solvent is dried, or may be used in a semi-cured (B-stage) state as needed. The thickness of the resin layer of the single layer or resin sheet of the present embodiment can be adjusted according to the concentration of the solution of the resin composition of the present embodiment and the coating thickness, and is not particularly limited, and is preferably 0.1 to 500 μm, since the solvent tends to remain during drying when the coating thickness is generally increased.
< agent for reducing dielectric constant and/or dielectric loss tangent >
The dielectric constant and/or dielectric loss tangent reducing agent of the present embodiment contains a bismaleimide compound (B) represented by formula (1). The dielectric constant and/or dielectric loss tangent of the resin composition can be reduced by blending the bismaleimide compound represented by the formula (1) with a maleimide compound other than the cyanate ester compound (a) and the bismaleimide compound (B), or with another resin component. The dielectric constant and/or dielectric loss tangent reducing agent of the present embodiment is particularly effective as a dielectric loss tangent reducing agent. The preferable range of the bismaleimide compound represented by the formula (1) is the same as described above.
Examples
The present invention will be described in more detail with reference to examples. The materials, amounts, ratios, processing contents, processing steps and the like shown in the following examples may be appropriately changed without departing from the gist of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below.
Synthesis example 1 Synthesis of Naphthol aralkyl type cyanate ester Compound (SNCN)
300g (1.28 mol in terms of OH group) of 1-naphthol aralkyl resin (available from Nippon iron Co., Ltd.) and 194.6g (1.92mol) of triethylamine (1.5 mol based on 1mol of hydroxyl group) were dissolved in 1800g of dichloromethane to prepare solution 1.
Solution 1 was poured into cyanogen chloride (125.9 g, 2.05mol) (1.6 mol based on 1mol of hydroxyl group), methylene chloride (293.8 g), 36% hydrochloric acid (194.5 g, 1.92mol) (1.5 mol based on 1mol of hydroxyl group), and water (1205.9 g) with stirring while maintaining the liquid temperature at-2 ℃ to-0.5 ℃ for 30 minutes. After completion of the injection of solution 1, the mixture was stirred at the same temperature for 30 minutes, and then a solution (solution 2) in which 65g (0.64mol) of triethylamine (0.5 mol based on 1mol of the hydroxyl group) was dissolved in 65g of methylene chloride was injected over 10 minutes. After the end of the injection of solution 2, the reaction was terminated by stirring at the same temperature for 30 minutes.
The reaction solution was then allowed to stand to separate the organic and aqueous phases. The organic phase obtained was washed 5 times with 1300g of water. The conductivity of the wastewater from the 5 th washing was 5. mu.S/cm, and it was confirmed that the ionic compounds to be removed were sufficiently removed by washing with water.
The organic phase after washing with water was concentrated under reduced pressure, and finally concentrated and dried at 90 ℃ for 1 hour to obtain 331g of the objective naphthol aralkyl type cyanate ester compound (SNCN) (orange viscous substance). The mass average molecular weight of the obtained SNCN was 600. Further, the IR spectrum of SNCN showed 2250cm-1(cyanate ester group) and does not show hydroxyl group absorption. The equivalent of the cyanate group of the obtained SNCN was 256 g/eq.
Synthesis example 2 Synthesis of bismaleimide Compound (BMI-bisannilin-M) >
17.23g (50.0mmol) of 1, 3-bis [2- (4-aminophenyl) -2-propyl ] benzene, manufactured by Tokyo chemical industry Co., Ltd., and 120.0g of N, N-dimethylformamide as a solvent were charged into a flask equipped with a stirrer, a nitrogen introduction tube, a dean-Stark trap, a condenser and a thermometer, and dissolved with stirring while introducing nitrogen. To this solution, 10.8g (110mmol) of maleic anhydride was added and stirred at room temperature for evening-out. Thereafter, 0.951g (5.00mmol) of p-toluenesulfonic acid monohydrate as a catalyst and 60g of toluene as a dehydration azeotropic solvent were charged, and azeotropic stirring was carried out for 6 hours. At this time, evaporation of toluene and water occurred, and a part of them was condensed in the condenser. After separating the water and toluene captured by the dean-Stark trap, only toluene was refluxed in the system, and a part thereof was distilled off from the upper part of the cooling tube to the outside of the system by flowing nitrogen gas.
After cooling the reaction mixture, the toluene was distilled off in an evaporator. Then, the obtained solution was put into a 1 mass% aqueous sodium hydrogencarbonate solution to remove maleic anhydride and p-toluenesulfonic acid which were excessively used. The obtained crude product was dissolved in N, N-dimethylformamide, reprecipitated by adding methanol, and the precipitate was filtered and dried. This operation was repeated 3 times to obtain 4, 4' -bismaleimide diphenyl ether (yield 70%).
The equivalent of the maleimide group of BMI-bisannilin-M obtained was 252.3 g/eq.
Synthesis example 3 Synthesis of bismaleimide Compound (BMI-bisannilin-P) >
17.23g (50.0mmol) of 1, 4-bis [2- (4-aminophenyl) -2-propyl ] benzene, manufactured by Tokyo chemical industry Co., Ltd., and 120.0g of N, N-dimethylformamide as a solvent were charged into a flask equipped with a stirrer, a nitrogen introduction tube, a dean-Stark trap, a condenser and a thermometer, and dissolved with stirring while introducing nitrogen. To this solution, 10.8g (110mmol) of maleic anhydride was added and stirred at room temperature for evening-out. Thereafter, 0.951g (5.00mmol) of p-toluenesulfonic acid monohydrate as a catalyst and 60g of toluene as a dehydration azeotropic solvent were charged, and azeotropic stirring was carried out for 6 hours. At this time, evaporation of toluene and water occurred, and a part of them was condensed in the condenser. After separating the water and toluene captured by the dean-Stark trap, only toluene was refluxed in the system, and a part thereof was distilled off from the upper part of the cooling tube to the outside of the system by flowing nitrogen gas.
After cooling the reaction mixture, the toluene was distilled off in an evaporator. Then, the obtained solution was put into a 1 mass% aqueous sodium hydrogencarbonate solution to remove maleic anhydride and p-toluenesulfonic acid which were excessively used. The obtained crude product was dissolved in N, N-dimethylformamide, reprecipitated by adding methanol, and the precipitate was filtered and dried. This operation was repeated 3 times to obtain 4, 4' -bismaleimide diphenyl ether (yield 70%).
The equivalent of the functional group of BMI-bisannilin-P obtained was 252.3 g/eq.
< example 1>
Using methyl ethyl ketone as a solvent, 50 parts by mass of SNCN obtained in synthesis example 1, 20 parts by mass of BMI-bisanin-M obtained in synthesis example 2, 30 parts by mass of a biphenyl aralkyl type polymaleimide compound ("MIR-3000", manufactured by japan chemical corporation, equivalent of maleimide group is 275g/eq), 0.5 part by mass of TPIZ (2,4, 5-triphenylimidazole, curing accelerator), and 0.10 part by mass of zinc octoate ("Oct-Zn", manufactured by japan chemical industry co., ltd., curing accelerator) were dissolved so that the solid content concentration became 50% by mass, and mixed to obtain a varnish. The content of each component represents the amount of solid component. The appearance of the resulting varnish was evaluated according to the method described later.
Methyl ethyl ketone was evaporated and distilled off from the resulting varnish to obtain a mixed resin powder. The mixed resin powder was filled into a mold having a thickness of 0.8mm and a side of 1mm of 100mm under a pressure of 40kg/cm2Then, the mixture was vacuum-pressed at 230 ℃ for 120 minutes to obtain a test piece of a cured product having 1 side of 100mm and a thickness of 0.8 mm.
The water absorption, electrical properties (Dk and Df), and weight loss on heating were measured on the obtained test piece having a thickness of 0.8mm by the following methods.
< appearance of varnish >)
The appearance of the resulting varnish was evaluated visually as follows. Evaluation A to C were at practical levels.
A: uniform and no precipitate was observed.
B: uniform and substantially no precipitate was observed.
C: slightly inhomogeneous, and some precipitates were observed.
D: non-uniform, and many precipitates were observed.
< Water absorption >
Using the obtained test piece having a thickness of 0.8mm, the water absorption was calculated from the change in weight after steam treatment at 120 ℃ under 0.1MPa for 5 hours in accordance with JIS C6481 using a Pressure Cooker (PCT) tester. In JIS C6481, the sample size was changed to 30 mm. times.30 mm for a test piece having a thickness of 0.8 mm.
The pressure cooker testing machine used was PC-3 type, a product of Hill Kaisha.
The results are shown in table 1 below.
< < Electrical characteristics (Dk and Df) >)
The dielectric constant (Dk) and the dielectric loss tangent (Df) at 10GHz were measured using a perturbation method cavity resonator for the obtained test piece having a thickness of 0.8 mm.
The perturbation cavity resonator was made using Agilent Technologies, product inc. Agilent8722 ES.
The results are shown in table 1 below.
Heating weight loss
The thermal analysis of the cured product was performed using a calorimeter under a nitrogen atmosphere at a temperature rise rate of 10 ℃ per minute.
The calorimetry apparatus used "TGA 5200" by SII Nanotechnology, Inc.
The results are shown in table 1 below.
< example 2>
In example 1, the procedure was repeated in the same manner as in example 3 except that BMI-Bisanilin-P obtained in Synthesis example 3 was changed to BMI-Bisanilin-M in the same amount. The results are shown in table 1 below.
< comparative example 1>
The procedure of example 1 was repeated in the same manner except that BMI-bisannilin-M was not used and the MIR-3000 content was 50 parts by mass. The results are shown in table 1 below.
< comparative example 2>
The procedure of example 1 was repeated in the same manner except that SNCN and MIR-3000 were not used and the content of BMI-Bisanilin-M was changed to 100 parts by mass. The results are shown in table 1 below.
< comparative example 3>
The procedure of example 1 was repeated in the same manner except that SNCN, MIR-3000 and BMI-Bisanilin-M were not used and the content of BMI-Bisanilin-P was changed to 100 parts by mass. The results are shown in table 1 below.
[ Table 1]
From the above results, it was found that the resin compositions of examples 1 and 2 maintained good varnish appearance and low water absorption rate equivalent to those of comparative example 1, and further, the weight loss on heating was reduced as compared with comparative example 1, and further, the electrical characteristics were improved. In particular, Df is significantly reduced. In comparative examples 2 and 3, the appearance of the varnish was D, which was not practically usable.
< example 3>
50 parts by mass of SNCN obtained in Synthesis example 1, 20 parts by mass of BMI-bisanin-M obtained in Synthesis example 2, 30 parts by mass of a biphenyl aralkyl type polymaleimide compound ("MIR-3000", manufactured by Nippon chemical Co., Ltd.), 100 parts by mass of spherical silica (SC2050-MB, manufactured by Admatechs, Ltd., average particle diameter of 0.5 μ M), 0.5 part by mass of TPIZ (2,4, 5-triphenylimidazole, curing accelerator), and 0.10 part by mass of zinc octylate ("Oct-Zn", manufactured by Nippon chemical industries, Ltd., curing accelerator) were dissolved in methyl ethyl ketone as a solvent so that the solid content concentration became 50% by mass, and mixed to obtain a varnish. The contents described above represent the amounts of solid components. The appearance of the resulting varnish was evaluated according to the method described later.
The varnish thus obtained was impregnated into and applied to E glass cloth having a thickness of 0.1mm, and the resultant was dried by heating at 165 ℃ for 5 minutes using a dryer (pressure-resistant explosion-proof steam dryer, manufactured by Gaussa Corp.) to obtain a prepreg containing 50% by mass of a resin composition and 50% by mass of glass cloth. The appearance of the resulting prepreg was evaluated according to the method described below.
The obtained prepreg was stacked with 4 or 8 sheets of copper foil (3EC-M3-VLP, manufactured by Mitsui Metal mining Co., Ltd.) of 12 μ M thickness on both sides, and the pressure was 40kg/cm2Vacuum pressing was carried out at 220 ℃ for 120 minutes to obtain copper clad laminates having thicknesses of 0.4mm and 0.8 mm.
The obtained copper clad laminate was measured for peel strength, bending properties, water absorption, electrical characteristics (Dk and Df), glass transition temperature, flame retardancy, thermal expansion coefficient, weight loss on heating, and thermal conductivity.
< appearance of varnish >)
The appearance of the resulting varnish was evaluated visually as follows. Evaluation A to C were at practical levels.
A: uniform and no precipitate was observed.
B: uniform and substantially no precipitate was observed.
C: slightly inhomogeneous, and some precipitates were observed.
D: non-uniform, and many precipitates were observed.
< prepreg appearance >)
The obtained prepreg was visually evaluated for appearance as follows. Evaluation A to C were at practical levels.
A: uniform and no precipitate was observed.
B: uniform and substantially no precipitate was observed.
C: slightly inhomogeneous, and some precipitates were observed.
D: non-uniform, and many precipitates were observed.
< Peel Strength >)
The peel strength of the copper foil was measured 3 times using a test piece (30mm × 150mm × 0.8mm thickness) obtained by cutting the copper clad laminate having a thickness of 0.8mm obtained as described above, according to the copper clad laminate test method for printed wiring board of JIS C6481 (see 5.7 peel strength), and the average value of the lower limit values was used as the measured value. The results are shown in Table 2.
Physical Property of bending
The copper foil on the surface layer of the copper clad laminate having a thickness of 0.8mm obtained above was removed by etching, both end portions of the test piece were supported by an Autograph testing machine according to JIS K6911 with supporting points to form both end supporting rubber edges, and the maximum bending stress when a concentrated load was applied from above to the central portion was measured to obtain the bending strength.
Further, using a test piece from which the copper foil of the copper clad laminate was removed, the bending modulus was obtained by measuring the deformation resistance of the test piece against the bending stress of the linear portion of the load deflection curve within the elastic limit as the bending stress per unit strain using an Autograph tester in accordance with JIS K6911.
AG-Xplus manufactured by Shimadzu corporation was used as the Autograph testing machine.
The results are shown in Table 2.
< Water absorption >
The water absorption was calculated from the weight change after the treatment at 120 ℃ and 0.1MPa for 5 hours by using a Pressure Cooker (PCT) tester in accordance with JIS C6481, for a sample obtained by cutting the copper clad laminate having a thickness of 0.8mm into pieces of 30 mm. times.30 mm.
The pressure cooker testing machine used was PC-3 type, a product of Hill Kaisha.
The results are shown in Table 2.
< Electrical characteristics >
Using a sample of a copper foil from which the resulting copper-clad laminate having a thickness of 0.4mm and a thickness of 0.8mm was removed by etching, the dielectric constant (Dk) and the dielectric loss tangent (Df) were measured at 2GHz and 10GHz, respectively.
The perturbation cavity resonator was made using Agilent Technologies, product inc. Agilent8722 ES.
The results are shown in Table 2.
Glass transition temperature
The glass transition temperature (Tg) was determined as follows: the copper foils on both sides of the copper clad laminate having a thickness of 0.8mm obtained were removed by etching, and then measured by a Dynamic Mechanical Analysis (DMA) method using a Dynamic viscoelasticity analyzer in accordance with JIS C6481. In table 2 below, E "represents a loss modulus, and tan δ represents a loss tangent.
The dynamic viscoelasticity analyzer was a TA Instruments system.
The results are shown in Table 2.
Flame retardancy
The copper foils on both sides of the metal-clad laminates obtained in examples and comparative examples were removed by etching. Then, using the test piece from which the copper foil on both sides was removed, a flame retardancy test was performed according to the UL94 vertical burning test method.
The results are shown in Table 2.
< thermal expansion Rate >
Using a sample of the copper foil of the copper clad laminate having a thickness of 0.8mm obtained by etching removal, the thermal expansion coefficient (x-direction, y-direction, and z-direction) of the glass cloth was measured with respect to the insulating layer of the laminate by the TMA method (Thermo-mechanical analysis) specified in JlS C6481, and the value thereof was obtained. Specifically, copper foils on both sides of the copper clad laminate obtained as described above were etched and removed to prepare a 4.5mm × 16mm evaluation substrate, and the thermal expansion coefficients (ppm/K) in the x, y, and z directions were measured at 60 to 120 ℃ respectively by raising the temperature from 40 ℃ to 340 ℃ at 10 ℃ per minute using a thermomechanical analyzer (TA Instruments).
The results are shown in Table 2.
Heating weight loss
A sample from which the copper foil of the copper-clad laminate having a thickness of 0.8mm obtained by etching was removed was analyzed thermally under a nitrogen atmosphere at a temperature rise rate of 10 ℃/min using a calorimeter.
The calorimetry apparatus used "TGA 5200" by SII Nanotechnology, Inc.
The results are shown in Table 2.
< thermal conductivity >
The density and specific heat of the copper clad laminates obtained in each example and comparative example were measured.
Specific heat was measured by means of DSC type Q100 from TA Instruments.
The thermal diffusivity of the copper-clad laminate in the thickness direction of the copper-clad laminate was measured.
Thermal diffusivity was determined using a xenon flash analyzer (Bruker: LFA447 Nanoflash). The thermal conductivity was calculated from the following equation.
Thermal conductivity (W/m. K)
Density (kg/m)3) Specific heat (kJ/kg. K). times.thermal diffusivity (m)2/S)×1000
The results are shown in Table 2.
< example 4>
In example 3, the procedure was repeated in the same manner as in example 3 except that BMI-Bisanilin-P obtained in Synthesis example 3 was changed to the same amount as BMI-Bisanilin-M. The results are shown in table 2 below.
< comparative example 4>
The procedure of example 3 was repeated in the same manner except that BMI-bisannilin-M was not used and the MIR-3000 content was 50 parts by mass. The results are shown in table 2 below.
[ Table 2]
From the foregoing results, it was revealed that the copper clad laminates of examples 3 and 4 maintained good varnish appearance, good prepreg appearance, high peel strength, high bending properties, low water absorption, low thermal expansion rate, and thermal conductivity equivalent to those of comparative example 4, and achieved higher Tg and less weight loss by heating than comparative example 4, and further improved electrical characteristics (reduced Dk and reduced Df).
Claims (18)
1. A resin composition comprising:
cyanate ester compound (A), and
a bismaleimide compound (B) represented by the following formula (1);
in the formula (1), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each independently represents an integer of 0 to 4.
2. The resin composition according to claim 1, wherein in the formula (1), X is an alkylene group having 1 to 3 carbon atoms, and R is1~R3Each independently represents a hydrogen atom, a methyl group or an ethyl group, and each independently represents an integer of 0 to 2.
4. the resin composition according to any one of claims 1 to 3, further comprising a solvent.
5. The resin composition according to claim 4, wherein the content of the bismaleimide compound (B) is 0.1 to 30% by mass of the resin composition.
6. The resin composition according to any one of claims 1 to 5, wherein the content ratio of the cyanate ester compound (A) and the bismaleimide compound (B) is 0.01 or more and less than 1.1, as represented by an equivalent ratio of an unsaturated imide group of the bismaleimide compound (B) to a cyanate ester group of the cyanate ester compound (A) (equivalent of unsaturated imide group/equivalent of cyanate ester group).
7. The resin composition according to any one of claims 1 to 6, further comprising 1 or more selected from the group consisting of a maleimide compound other than the bismaleimide compound (B), an epoxy resin, a phenol resin, an oxetane resin, a benzoxazine compound, a compound having a polymerizable unsaturated group, a modified polyphenylene ether end-modified with a substituent containing a carbon-carbon unsaturated double bond (other than maleimide), an elastomer, and an active ester compound.
8. The resin composition according to any one of claims 1 to 7, further comprising a filler (C).
9. The resin composition according to claim 8, wherein the content of the filler (C) is 50 to 1600 parts by mass with respect to 100 parts by mass of the total amount of the resin components in the resin composition.
10. The resin composition according to any one of claims 1 to 9, which is a low dielectric constant material and/or a low dielectric loss tangent material.
11. A cured product of the resin composition according to any one of claims 1 to 10.
12. A prepreg formed from a substrate and the resin composition according to any one of claims 1 to 10.
13. A metal-foil-clad laminate comprising: a layer formed from at least 1 sheet of the prepreg of claim 12; and a metal foil disposed on one or both surfaces of the layer formed of the prepreg.
14. A resin tablet comprising: a support body; and a layer formed of the resin composition according to any one of claims 1 to 10, disposed on a surface of the support.
15. A printed circuit board, comprising: an insulating layer and a conductor layer disposed on a surface of the insulating layer,
the insulating layer includes: at least one of a layer formed from the resin composition according to any one of claims 1 to 10 and a layer formed from the prepreg according to claim 12.
16. A process for producing a resin composition comprising a cyanate ester compound (A) and a bismaleimide compound (B) represented by the following formula (1),
the manufacturing method comprises the following steps: mixing a cyanate ester compound (A), a bismaleimide compound (B) and a solvent, wherein the content of the bismaleimide compound (B) is 0.1-30% by mass of the resin composition;
in the formula (1), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each independently represents an integer of 0 to 4.
17. The method for producing a resin composition according to claim 16, wherein the resin composition further contains 1 or more selected from the group consisting of a maleimide compound other than the bismaleimide compound (B), an epoxy resin, a phenol resin, an oxetane resin, a benzoxazine compound, a compound having a polymerizable unsaturated group, a modified polyphenylene ether end-modified with a substituent containing a carbon-carbon unsaturated double bond (other than maleimide), an elastomer, and an active ester compound.
18. A dielectric constant and/or dielectric loss tangent reducing agent comprising a bismaleimide compound (B) represented by the following formula (1);
in the formula (1), X represents an organic group having 1 to 12 carbon atoms, R1~R3Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and each independently represents an integer of 0 to 4.
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JP (1) | JP7363781B2 (en) |
KR (1) | KR20210025526A (en) |
CN (1) | CN112313265B (en) |
TW (1) | TWI830741B (en) |
WO (1) | WO2020004211A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI839038B (en) | 2022-12-23 | 2024-04-11 | 南亞塑膠工業股份有限公司 | Resin composition |
CN117886999A (en) * | 2024-03-14 | 2024-04-16 | 西南石油大学 | Preparation method and application of benzoxazine-olefin copolymer for deep well cementation |
Families Citing this family (10)
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WO2021149733A1 (en) * | 2020-01-24 | 2021-07-29 | 三菱瓦斯化学株式会社 | Resin composition, resin sheet, prepreg, and printed wiring board |
JPWO2022054867A1 (en) * | 2020-09-11 | 2022-03-17 | ||
US20230399511A1 (en) * | 2020-09-11 | 2023-12-14 | Panasonic Intellectual Property Management Co., Ltd. | Resin composition, prepreg, resin-coated film, resin-coated metal foil, metal-clad laminate, and wiring board |
CN114672168B (en) * | 2020-12-24 | 2023-06-06 | 广东生益科技股份有限公司 | Halogen-free flame-retardant resin composition and application thereof |
JP7157277B1 (en) * | 2021-02-25 | 2022-10-19 | 日本化薬株式会社 | Curable resin composition, prepreg and cured product thereof |
TWI798734B (en) * | 2021-06-30 | 2023-04-11 | 南亞塑膠工業股份有限公司 | Thermosetting resin material, prepreg, and metal substrate |
KR102591854B1 (en) * | 2021-12-30 | 2023-10-23 | 숙명여자대학교산학협력단 | Manufacturing method of copper foil surface adhesive layer for fccl and fccl applied by same |
WO2024090410A1 (en) * | 2022-10-26 | 2024-05-02 | 三菱瓦斯化学株式会社 | Resin composition, cured product, prepreg, metal-foil-clad laminate board, resin composite sheet, and printed wiring board |
WO2024090408A1 (en) * | 2022-10-26 | 2024-05-02 | 三菱瓦斯化学株式会社 | Resin composition, cured product, prepreg, metal foil-clad laminate, resin composite sheet, and printed wiring board |
TWI835402B (en) * | 2022-11-11 | 2024-03-11 | 南亞塑膠工業股份有限公司 | Resin composition |
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- 2019-06-20 JP JP2020527454A patent/JP7363781B2/en active Active
- 2019-06-20 WO PCT/JP2019/024464 patent/WO2020004211A1/en active Application Filing
- 2019-06-20 CN CN201980042158.6A patent/CN112313265B/en active Active
- 2019-06-20 KR KR1020207036842A patent/KR20210025526A/en not_active Application Discontinuation
- 2019-06-20 TW TW108121427A patent/TWI830741B/en active
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI839038B (en) | 2022-12-23 | 2024-04-11 | 南亞塑膠工業股份有限公司 | Resin composition |
CN117886999A (en) * | 2024-03-14 | 2024-04-16 | 西南石油大学 | Preparation method and application of benzoxazine-olefin copolymer for deep well cementation |
Also Published As
Publication number | Publication date |
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WO2020004211A1 (en) | 2020-01-02 |
JPWO2020004211A1 (en) | 2021-08-05 |
KR20210025526A (en) | 2021-03-09 |
TWI830741B (en) | 2024-02-01 |
TW202000784A (en) | 2020-01-01 |
CN112313265B (en) | 2024-04-23 |
JP7363781B2 (en) | 2023-10-18 |
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