TW202402737A - Maleimide compound,curable resin compositi0n,and cured product thereof,and amine compound and reaction product of amine compound and maleic anhydride - Google Patents
Maleimide compound,curable resin compositi0n,and cured product thereof,and amine compound and reaction product of amine compound and maleic anhydride Download PDFInfo
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- TW202402737A TW202402737A TW112111552A TW112111552A TW202402737A TW 202402737 A TW202402737 A TW 202402737A TW 112111552 A TW112111552 A TW 112111552A TW 112111552 A TW112111552 A TW 112111552A TW 202402737 A TW202402737 A TW 202402737A
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- -1 Maleimide compound Chemical class 0.000 title claims abstract description 179
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000000047 product Substances 0.000 title abstract description 41
- 239000007795 chemical reaction product Substances 0.000 title abstract description 5
- 229920005989 resin Polymers 0.000 title description 50
- 239000011347 resin Substances 0.000 title description 50
- 239000011342 resin composition Substances 0.000 claims abstract description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims description 87
- 239000000376 reactant Substances 0.000 claims description 22
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 6
- 239000007870 radical polymerization initiator Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
- 239000003822 epoxy resin Substances 0.000 description 75
- 229920000647 polyepoxide Polymers 0.000 description 75
- 238000006243 chemical reaction Methods 0.000 description 44
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 32
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 27
- 229920001955 polyphenylene ether Polymers 0.000 description 27
- 238000006116 polymerization reaction Methods 0.000 description 25
- 239000000126 substance Substances 0.000 description 22
- 239000000463 material Substances 0.000 description 20
- 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 19
- 238000005227 gel permeation chromatography Methods 0.000 description 19
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
- 239000005062 Polybutadiene Substances 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 229920002857 polybutadiene Polymers 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 17
- 150000002430 hydrocarbons Chemical group 0.000 description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 17
- 150000002989 phenols Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000004793 Polystyrene Substances 0.000 description 15
- 239000003112 inhibitor Substances 0.000 description 15
- 229920002223 polystyrene Polymers 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 239000004927 clay Substances 0.000 description 13
- 239000011521 glass Substances 0.000 description 13
- 229920003986 novolac Polymers 0.000 description 13
- 239000003505 polymerization initiator Substances 0.000 description 13
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- 239000011256 inorganic filler Substances 0.000 description 12
- 229910003475 inorganic filler Inorganic materials 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 239000004643 cyanate ester Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 238000000465 moulding Methods 0.000 description 10
- 239000005011 phenolic resin Substances 0.000 description 10
- 239000004065 semiconductor Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- 239000003377 acid catalyst Substances 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 238000001723 curing Methods 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- 238000003475 lamination Methods 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 229930185605 Bisphenol Natural products 0.000 description 8
- 229920000049 Carbon (fiber) Polymers 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 239000004917 carbon fiber Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000003063 flame retardant Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 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 7
- 239000012948 isocyanate Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000003566 sealing material Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000010146 3D printing Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000004611 light stabiliser Substances 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 5
- 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 5
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 5
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 229920006132 styrene block copolymer Polymers 0.000 description 5
- 239000003799 water insoluble solvent Substances 0.000 description 5
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 4
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical group OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical group 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 150000003254 radicals Chemical class 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
- 239000002966 varnish Substances 0.000 description 4
- 239000002759 woven fabric Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-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
- 229910000831 Steel Inorganic materials 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 150000004074 biphenyls Chemical class 0.000 description 3
- TYMZLIDQEUWXEL-UHFFFAOYSA-N bis(2,3-dimethylphenyl) hydrogen phosphate Chemical compound CC1=CC=CC(OP(O)(=O)OC=2C(=C(C)C=CC=2)C)=C1C TYMZLIDQEUWXEL-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 3
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- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
- IJQXGKBNDNQWAT-UHFFFAOYSA-L zinc;docosanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O IJQXGKBNDNQWAT-UHFFFAOYSA-L 0.000 description 1
- PORPEXMDRRVVNF-UHFFFAOYSA-L zinc;octadecyl phosphate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCOP([O-])([O-])=O PORPEXMDRRVVNF-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
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- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Description
本發明係關於順丁烯二醯亞胺化合物、硬化性樹脂組成物及其硬化物、以及胺化合物及胺化合物與順丁烯二醯酸酐之反應物,係適於使用在半導體密封材、印刷配線基板、組裝(build-up)積層板等電氣電子零件、碳纖維強化塑膠、玻璃纖維強化塑膠等輕量高強度材料、3D列印用途。 The present invention relates to maleimine compounds, curable resin compositions and cured products thereof, as well as amine compounds and reactants of amine compounds and maleic anhydride, which are suitable for use in semiconductor sealing materials and printing. Electrical and electronic components such as wiring boards and build-up laminates, lightweight and high-strength materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics, and 3D printing applications.
近年來,由於搭載電氣電子零件之積層板的應用領域擴大,故對其要求的特性變得更加廣泛且高度化。以往的半導體晶片主要是搭載在金屬製引線框架,惟中央處理裝置(以下示為CPU)等的高處理能力的半導體晶片越來越常被搭載在由高分子材料所製成的積層板。 In recent years, as the application fields of laminate boards equipped with electrical and electronic components have expanded, the characteristics required for them have become broader and more sophisticated. In the past, semiconductor wafers were mainly mounted on metal lead frames, but high-processing power semiconductor wafers such as central processing units (hereinafter referred to as CPUs) are increasingly being mounted on laminates made of polymer materials.
並且,為了滿足屬於耐熱積層板之標準值的加熱時特性,至少要求160℃以上之耐熱性(Tg)(非專利文獻1)。 Furthermore, in order to satisfy the heating characteristics which are standard values for heat-resistant laminated boards, a heat resistance (Tg) of at least 160° C. or higher is required (Non-Patent Document 1).
此外,現在正在加速開發之第5代通信系統「5G」係預計會有更進一步之大容量化與高速通信。低介電正切材料之需求係逐日升高,要求至少在10GHz時為0.005以下之介電正切。 In addition, the fifth generation communication system "5G", which is currently being developed at an accelerated pace, is expected to have further large-capacity and high-speed communications. The demand for low dielectric tangent materials is increasing day by day, requiring a dielectric tangent below 0.005 at least at 10GHz.
更且,在汽車領域中,隨著電子化的增進,有時會在發動機驅動部附近配置精密電子設備,因此而要求更高水準的耐熱耐濕性。SiC半導體開始使用於電車和空調等,由於半導體元件之密封材要求極高的耐熱性,故以往之環氧樹脂密封材係無法應付該要求。 Furthermore, in the automotive field, as electronics advances, precision electronic equipment is sometimes installed near the engine drive unit, and therefore a higher level of heat and moisture resistance is required. SiC semiconductors are beginning to be used in trains, air conditioners, etc. Since sealing materials for semiconductor components require extremely high heat resistance, conventional epoxy resin sealing materials cannot meet this requirement.
鑑於此背景,已正在探討能夠兼具耐熱性與低介電正切特性的高分子材料。例如,專利文獻1提案了一種組成物,其包含順丁烯二醯亞胺樹脂及具有丙烯基之酚樹脂。此外,專利文獻2揭示了一種烯丙基醚樹脂,其係以烯丙基取代羥基而成者。 In view of this background, polymer materials that have both heat resistance and low dielectric tangent properties are being studied. For example, Patent Document 1 proposes a composition including a maleimide resin and a phenol resin having an acryl group. Furthermore, Patent Document 2 discloses an allyl ether resin in which a hydroxyl group is substituted with an allyl group.
此外,近年來,3D列印係以作為三維建模手法而備受矚目,該3D列印手法係開始應用於如航空、宇宙、車輛、以及此等所用之電子零件的連接器等要求可靠性的領域中。尤其是光硬化系、熱硬化系之樹脂正被探討用於以立體光刻(Stereolithography,SLA)和數位光處理(Digital Light Processing,DLP)為代表的用途。因此,在以往之從模具來進行轉印之方法中,主要是要求形狀之穩定性、正確性,惟在3D列印用途中,則是要求耐熱性、機械特性、強靭性、阻燃性、甚至電氣特性等各種特性,並且已在進行其材料的開發。此外,在使用於結構構件之情況下,則有由於吸濕等而導致特性變化的課題。現在,丙烯酸酯樹脂和環氧樹脂係應用於如此之用途中。 In addition, in recent years, 3D printing has attracted much attention as a three-dimensional modeling method. This 3D printing method has begun to be used in aerospace, aerospace, vehicles, and connectors of electronic parts used in these areas that require reliability. in the field. In particular, photocuring and thermosetting resins are being explored for applications represented by stereolithography (SLA) and digital light processing (DLP). Therefore, in the previous methods of transferring from molds, the stability and accuracy of the shape are mainly required, but in 3D printing applications, heat resistance, mechanical properties, toughness, flame retardancy, and even various properties such as electrical properties, and the development of its materials is already underway. In addition, when used in structural members, there is a problem of changes in characteristics due to moisture absorption and the like. Currently, acrylate resins and epoxy resins are used for such purposes.
[先前技術文獻] [Prior technical literature]
[專利文獻] [Patent Document]
[專利文獻1]日本特開平04-359911號公報 [Patent Document 1] Japanese Patent Application Publication No. 04-359911
[專利文獻2]國際公開2016/002704號 [Patent Document 2] International Publication No. 2016/002704
[非專利文獻1]片山統夫, “基礎講座「基板材料」第5回 耐熱玻璃環氧積層板”, Circuit Technology, 一般社團法人電子學實裝學會, 1993, Vol.8, No.6, p.505-511 [Non-patent document 1] Touo Katayama, "Basic Lecture "Substrate Materials" 5th Heat-Resistant Glass Epoxy Laminated Board", Circuit Technology, Electronics Manufacturing Society, 1993, Vol.8, No.6, p.505-511
然而,在包含順丁烯二醯亞胺樹脂與具有丙烯基的酚樹脂之組成物中,由於在硬化反應時未參與反應的酚性羥基會殘留,因而難謂電氣特性充分。 However, in a composition containing a maleimide resin and a phenol resin having an acryl group, since phenolic hydroxyl groups that did not participate in the reaction during the curing reaction remain, it is difficult to say that the electrical properties are sufficient.
此外,在經烯丙基取代羥基的烯丙基醚樹脂中,顯示在190℃中會發生克萊森重排(Claisen Rearrangement),故在屬於一般基板之成型溫度的200℃中會產生無助於硬化反應的酚性羥基,從而無法滿足電氣特性。 In addition, in allyl ether resins with allyl groups substituting hydroxyl groups, Claisen rearrangement is shown to occur at 190°C, so it will cause helplessness at 200°C, which is the molding temperature of general substrates. Due to the phenolic hydroxyl group involved in the hardening reaction, the electrical properties cannot be satisfied.
此外,在應用於3D列印用途之丙烯酸酯樹脂和環氧樹脂之硬化物中,會包含大量的酯鍵、醚鍵以及羥基,吸濕特性不充分。 In addition, hardened products of acrylic resins and epoxy resins used in 3D printing contain a large number of ester bonds, ether bonds and hydroxyl groups, resulting in insufficient hygroscopic properties.
本發明係鑑於如此狀況而創研者,其目的係提供一種具有高耐熱性、低介電特性優異、良好硬化性之順丁烯二醯亞胺化合物、硬化性樹脂組成物及其硬化物,以及作為其原料的胺化合物及胺化合物與順丁烯二醯酸酐之反應物。 The present invention was created in view of such a situation, and its purpose is to provide a maleimide compound, a curable resin composition, and a cured product that have high heat resistance, excellent low dielectric properties, and good curability. As well as the amine compound and the reaction product of the amine compound and maleic anhydride as its raw material.
亦即,本發明關於下述〔1〕至〔8〕。又,本發明中之「(數值1)至(數值2)」係表示包含其上下限值。 That is, the present invention relates to the following [1] to [8]. In addition, "(numerical value 1) to (numerical value 2)" in the present invention means including the upper and lower limits thereof.
〔1〕一種下述式(1)所示之順丁烯二醯亞胺化合物, [1] A maleimide compound represented by the following formula (1),
(式(1)中,存在複數個之R係分別獨立地存在,且表示碳數1至10之烴基或鹵化烷基。X係如下述式(2)所示。m為0至4之整數,n為重複數,n之平均值nave符合1≦nave≦20), (In formula (1), plural R's exist independently and represent a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms. X is represented by the following formula (2). m is an integer from 0 to 4 , n is the number of repetitions, the average n ave of n conforms to 1≦n ave ≦20),
(式(2)中,存在複數個之R係分別獨立地存在,且表示碳數1至10之烴基或鹵化烷基。p表示0至4之整數,q表示0至3之整數。r為重複數,r之平均值rave符合1≦rave≦20。*表示與前述式(1)之芳香環的鍵結位置)。 (In formula (2), plural R's exist independently and represent a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms. p represents an integer from 0 to 4, and q represents an integer from 0 to 3. r is The repeat number and the average r ave of r satisfy 1≦r ave ≦20. * indicates the bonding position to the aromatic ring of the aforementioned formula (1)).
〔2〕一種下述式(3)所示之順丁烯二醯亞胺化合物, [2] A maleimide compound represented by the following formula (3),
(式(3)中,X係如下述式(4)所示。n為重複數,n之平均值nave符合1.1≦nave≦20), ( In formula (3 ) ,
(式(4)中,存在複數個之R係分別獨立地存在,且表示碳數1至5之烴基。p表示0至4之整數,r為重複數,r之平均值rave符合1.1≦rave≦20。*表示與式(3)化合物之芳香環的鍵結位置)。 (In formula (4), a plurality of R exist independently and represent a hydrocarbon group with a carbon number of 1 to 5. p represents an integer from 0 to 4, r is the repeat number, and the average r ave of r conforms to 1.1≦ r ave ≦20. * indicates the bonding position with the aromatic ring of the compound of formula (3)).
〔3〕如前項〔2〕所述之順丁烯二醯亞胺化合物,其中,前述式(4)中,p為2,R之取代位置係相對於順丁烯二醯亞胺基而為鄰位。 [3] The maleimide compound as described in the preceding item [2], wherein in the formula (4), p is 2, and the substitution position of R is relative to the maleimide group. Ortho position.
〔4〕一種硬化性樹脂組成物,係含有:前項〔1〕至〔3〕中任一項所述之順丁烯二醯亞胺化合物。 [4] A curable resin composition containing the maleimide compound described in any one of the preceding paragraphs [1] to [3].
〔5〕如前項〔4〕所述之硬化性樹脂組成物,更含有自由基聚合起始劑。 [5] The curable resin composition as described in the preceding paragraph [4], further containing a radical polymerization initiator.
〔6〕一種硬化物,係由前項〔4〕或〔5〕所述之硬化性樹脂組成物所硬化而得者。 [6] A hardened product obtained by hardening the curable resin composition described in the preceding paragraph [4] or [5].
〔7〕一種下述式(5)所示之胺化合物, [7] An amine compound represented by the following formula (5),
(式(5)中,存在複數個之R係分別獨立地存在,且表示碳數1至10之烴基或鹵化烷基。p表示0至4之整數,q表示0至3之整數。r為重複數,r之平均值rave符合1≦rave≦20)。 (In formula (5), plural R's exist independently and represent a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms. p represents an integer from 0 to 4, and q represents an integer from 0 to 3. r is The number of repetitions, the average r ave of r is consistent with 1≦r ave ≦20).
〔8〕一種前項〔7〕所述之化合物與順丁烯二醯酸酐的反應物。 [8] A reaction product between the compound described in the preceding item [7] and maleic anhydride.
本發明之順丁烯二醯亞胺化合物的硬化物具有高耐熱性、低介電特性優異的特性。因而為有用於電氣電子零件之密封和電路基板、碳纖維複合材等的材料。 The cured product of the maleimide compound of the present invention has the characteristics of high heat resistance and excellent low dielectric properties. Therefore, it is a material used for sealing of electrical and electronic parts, circuit substrates, carbon fiber composite materials, etc.
圖1表示實施例1之胺化合物的GPC圖表。 Figure 1 shows a GPC chart of the amine compound of Example 1.
圖2表示實施例1之順丁烯二醯亞胺化合物的GPC圖表。 Figure 2 shows a GPC chart of the maleimide compound of Example 1.
圖3表示實施例1之順丁烯二醯亞胺化合物的1H-NMR圖表。 Fig. 3 shows a 1 H-NMR chart of the maleimide compound of Example 1.
圖4表示實施例2之胺化合物的GPC圖表。 Figure 4 shows a GPC chart of the amine compound of Example 2.
圖5表示實施例2之順丁烯二醯亞胺化合物的GPC圖表。 Figure 5 shows a GPC chart of the maleimide compound of Example 2.
圖6表示實施例2之順丁烯二醯亞胺化合物的1H-NMR圖表。 Fig. 6 shows a 1 H-NMR chart of the maleimide compound of Example 2.
圖7表示合成例1之胺化合物的GPC圖表。 FIG. 7 shows a GPC chart of the amine compound of Synthesis Example 1.
圖8表示合成例2之順丁烯二醯亞胺化合物的GPC圖表。 FIG. 8 shows a GPC chart of the maleimide compound of Synthesis Example 2.
本實施型態之順丁烯二醯亞胺化合物係如下述式(1)所示。 The maleimide compound of this embodiment is represented by the following formula (1).
(式(1)中,存在複數個之R係分別獨立地存在,且表示碳數1至10之烴基或鹵化烷基。X係如下述式(2)所示。m為0至4之整數,n為重複數,n之平均值nave符合1≦nave≦20。) (In formula (1), plural R's exist independently and represent a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms. X is represented by the following formula (2). m is an integer from 0 to 4 , n is the number of repetitions, and the average n ave of n conforms to 1≦n ave ≦20.)
(式(2)中,存在複數個之R係分別獨立地存在,且表示碳數1至10之烴基或鹵化烷基。p表示0至4之整數,q表示0至3之整數。r為重複數,r之平均值rave符合1≦rave≦20。*表示與前述式(1)之芳香環的鍵結位置。) (In formula (2), plural R's exist independently and represent a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms. p represents an integer from 0 to 4, and q represents an integer from 0 to 3. r is The repeat number and the average r ave of r satisfy 1 ≦ r ave ≦ 20. * indicates the bonding position to the aromatic ring of the aforementioned formula (1).)
前述式(1)及前述式(2)中,R為碳數1至10之烴基或鹵化烷基,惟較佳為碳數1至10之烴基,更佳為碳數1至5之烴基,特佳為碳數1至3之烴基。在R為碳數少者之情況下,暴露於高頻時會難以產生分子振動,因此,在上述記載中,若為碳數1至3之烴基則使電氣特性特別優異。 In the aforementioned formula (1) and the aforementioned formula (2), R is a hydrocarbon group with 1 to 10 carbon atoms or a halogenated alkyl group, but is preferably a hydrocarbon group with 1 to 10 carbon atoms, more preferably a hydrocarbon group with 1 to 5 carbon atoms. Particularly preferred is a hydrocarbon group having 1 to 3 carbon atoms. When R has a small number of carbon atoms, it is difficult to generate molecular vibration when exposed to high frequency. Therefore, in the above description, if it is a hydrocarbon group having 1 to 3 carbon atoms, the electrical characteristics will be particularly excellent.
前述式(1)中,m通常為0至4之整數,較佳為0至3,更佳為0至1,特佳為0。n為重複數,n之平均值nave通常符合1≦nave≦20,較佳為符合1.1≦nave≦20,更佳為符合1.1≦nave≦18,特佳為符合1.1≦nave≦15。關於n之平均值nave,可從由前述式(1)所示化合物之凝膠滲透層析術(GPC)的測定求出的數目平均分子量(Mn)之值等來計算出。數目平均分子量較佳為200以上且未達10000,更佳為1000以上且未達7500,特佳為2000以上且未達5000。若數目平均分子量未達10000,則易於以水洗進行純化,若為200以上,則目的化合物在溶劑餾去步驟中揮發的可能性小。 In the aforementioned formula (1), m is usually an integer from 0 to 4, preferably from 0 to 3, more preferably from 0 to 1, and particularly preferably 0. n is the number of repetitions, and the average n ave of n usually conforms to 1≦n ave ≦20, preferably 1.1≦n ave ≦20, more preferably 1.1≦n ave ≦18, particularly preferably 1.1≦n ave ≦15. The average value n ave of n can be calculated from the value of the number average molecular weight (Mn) determined by gel permeation chromatography (GPC) measurement of the compound represented by the aforementioned formula (1). The number average molecular weight is preferably from 200 to less than 10,000, more preferably from 1,000 to less than 7,500, and particularly preferably from 2,000 to less than 5,000. If the number average molecular weight is less than 10,000, purification by water washing is easy, and if it is 200 or more, the target compound is less likely to volatilize in the solvent distillation step.
前述式(2)中,p通常表示0至4之整數,較佳為0至3,更佳為0至2。q通常表示0至3之整數,較佳為0至2,更佳為0至1,特佳為0。r為重複數,r之平均值rave通常符合1≦rave≦20,較佳為符合1.1≦rave≦20,更佳為符合1.1≦rave≦18,特佳為符合1.1≦rave≦15。 In the aforementioned formula (2), p usually represents an integer from 0 to 4, preferably from 0 to 3, and more preferably from 0 to 2. q usually represents an integer from 0 to 3, preferably from 0 to 2, more preferably from 0 to 1, and particularly preferably 0. r is the number of repetitions. The average r ave of r usually conforms to 1≦r ave ≦20, preferably 1.1≦r ave ≦20, more preferably 1.1≦r ave ≦18, particularly preferably 1.1≦r ave ≦15.
前述式(1)所示之順丁烯二醯亞胺化合物之較佳一態樣,可列舉如下述式(3)所示之順丁烯二醯亞胺化合物。 A preferred aspect of the maleimide compound represented by the aforementioned formula (1) is a maleimide compound represented by the following formula (3).
(式(3)中,X係如下述式(4)所示。n為重複數,n之平均值nave符合1.1≦nave≦20。) (In formula ( 3 ) ,
(式(4)中,存在複數個之R係分別獨立地存在,且表示碳數1至5之烴基。p表示0至4之整數,r為重複數,r之平均值rave符合1.1≦rave≦20。*表示與式(3)化合物之芳香環的鍵結位置。) (In formula (4), a plurality of R exist independently and represent a hydrocarbon group with a carbon number of 1 to 5. p represents an integer from 0 to 4, r is the repeat number, and the average r ave of r conforms to 1.1≦ r ave ≦20. * indicates the bonding position to the aromatic ring of the compound of formula (3).)
前述式(4)中,就分子量控制、溶劑溶解性、介電特性、低吸水性、耐熱性之觀點而言,特佳係:R係相對於順丁烯二醯亞胺基而在鄰位取代2個取代基。 In the aforementioned formula (4), from the viewpoint of molecular weight control, solvent solubility, dielectric properties, low water absorption, and heat resistance, a particularly preferred one is: R is in the ortho position with respect to the maleimide group. Substitute 2 substituents.
關於前述式(1)所示之順丁烯二醯亞胺化合物,例如,可藉由下述式(5)所示之胺化合物的聚合物與順丁烯二醯酸酐的反應而得。下述式(5)所示之胺化合物的聚合與順丁烯二醯亞胺化反應可分別進行,惟可在甲磺酸等酸觸媒存在下進行一次下述式(5)之胺化合物的聚合反應及順丁烯二醯亞胺化反應。順丁烯二醯亞胺化反應之條件並無特別限定,所使用的溶劑可列舉例如甲苯、二甲苯等芳香族溶劑、環己烷、正己烷等脂肪族溶劑、二乙醚、二異丙醚等醚類、乙酸乙酯、乙酸丁酯等酯系溶劑、甲基異丁基酮、環戊酮等酮系溶劑之類的非水溶性溶劑,惟並非限定於此等,可併用2種以上。此外,除了前述非水溶性溶劑以外,亦可併用非質子性極性溶劑。可列舉例如二甲基碸、二甲基亞碸、二甲基甲醯胺、二甲基乙醯胺、1,3-二甲基-2-咪唑啉酮、N-甲基吡咯啶酮等,可併用2種以上。在使用非質子性極性溶劑之情況下,較佳係使用沸點高於併用的非水溶性溶劑者。反應時,因應需要,就觸媒而言,除了可使用鹽酸、磷酸、硫酸、甲酸、對甲苯磺酸、甲磺酸之外,還可使用氯化鋁、氯化鋅等路易斯酸、活性黏土 (activated clay)、酸性黏土、白碳、沸石、氧化矽-氧化鋁(silica-alumina)等固體酸、酸性離子交換樹脂等。此等係可單獨使用,亦可併用二種以上。相對於所使用之胺化合物之胺基1莫耳,觸媒之使用量通常為0.1至0.8莫耳,較佳為0.2至0.7莫耳。若觸媒之使用量過多,則反應溶液之黏度會過高而有難以攪拌之虞,若過少則有反應進行變慢之虞。此外,就醯亞胺化之助觸媒而言,亦可單獨使用或併用三乙胺等鹼性助觸媒。在將磺酸等作為觸媒時,可在以氫氧化鈉或氫氧化鉀等鹼金屬進行中和後再進行萃取步驟。針對萃取步驟,可單獨使用甲苯或二甲苯等芳香族烴溶劑,亦可併用環己烷或甲苯等非芳香族烴。萃取後,將有機層用水洗滌直到排水呈中性為止,使用蒸發器等餾去溶劑,而可獲得目的之順丁烯二醯亞胺化合物。 The maleimine compound represented by the aforementioned formula (1) can be obtained, for example, by the reaction of a polymer of an amine compound represented by the following formula (5) and maleic anhydride. The polymerization of the amine compound represented by the following formula (5) and the maleide imidization reaction can be performed separately, but the amine compound of the following formula (5) can be performed once in the presence of an acid catalyst such as methanesulfonic acid. Polymerization reaction and maleic acid imidization reaction. The conditions for the maleide imidization reaction are not particularly limited. Examples of solvents used include aromatic solvents such as toluene and xylene, aliphatic solvents such as cyclohexane and n-hexane, diethyl ether, and diisopropyl ether. Water-insoluble solvents such as ethers, ester solvents such as ethyl acetate and butyl acetate, and ketone solvents such as methyl isobutyl ketone and cyclopentanone are not limited to these, and two or more types may be used in combination. . In addition to the above-mentioned water-insoluble solvent, an aprotic polar solvent may be used in combination. Examples include dimethylsulfuric acid, dimethylsulfuric acid, dimethylformamide, dimethylacetylamide, 1,3-dimethyl-2-imidazolinone, N-methylpyrrolidone, and the like. , two or more types can be used together. When an aprotic polar solvent is used, it is preferable to use a water-insoluble solvent with a boiling point higher than that used in combination. During the reaction, if necessary, in terms of catalysts, in addition to hydrochloric acid, phosphoric acid, sulfuric acid, formic acid, p-toluenesulfonic acid, methanesulfonic acid, Lewis acids such as aluminum chloride and zinc chloride, and activated clay can also be used. (activated clay), acidic clay, white carbon, zeolite, silica-alumina (silica-alumina) and other solid acids, acidic ion exchange resin, etc. These systems can be used alone, or two or more types can be used in combination. The amount of catalyst used is usually 0.1 to 0.8 mole, preferably 0.2 to 0.7 mole, relative to 1 mole of the amine group of the amine compound used. If the amount of catalyst used is too much, the viscosity of the reaction solution will be too high, making it difficult to stir. If it is too small, the reaction may proceed slowly. In addition, as a cocatalyst for imidization, an alkaline cocatalyst such as triethylamine can also be used alone or in combination. When sulfonic acid or the like is used as a catalyst, the extraction step can be performed after neutralization with an alkali metal such as sodium hydroxide or potassium hydroxide. For the extraction step, aromatic hydrocarbon solvents such as toluene or xylene can be used alone, or non-aromatic hydrocarbon solvents such as cyclohexane or toluene can be used in combination. After extraction, the organic layer is washed with water until the drainage becomes neutral, and the solvent is distilled off using an evaporator or the like to obtain the desired maleimide compound.
(式(5)中,存在複數個之R係分別獨立地存在,且表示碳數1至10之烴基或鹵化烷基。p表示0至4之整數,q表示0至3之整數。r為重複數,r之平均值rave符合1≦rave≦20)。 (In formula (5), plural R's exist independently and represent a hydrocarbon group or a halogenated alkyl group having 1 to 10 carbon atoms. p represents an integer from 0 to 4, and q represents an integer from 0 to 3. r is The number of repetitions, the average r ave of r is consistent with 1≦r ave ≦20).
關於前述式(5)中之R的定義及p、q、rave之較佳範圍,係與前述式(2)相同。 The definition of R in the aforementioned formula (5) and the preferred ranges of p, q, r ave are the same as those in the aforementioned formula (2).
前述式(5)中,就分子量控制、溶劑溶解性、介電特性、低吸水性、耐熱性之觀點而言,在與胺基鍵結的苯環中,特佳係:p=2且R之取代位置係相對於胺基而為鄰位的2個位置。 In the aforementioned formula (5), from the viewpoint of molecular weight control, solvent solubility, dielectric properties, low water absorption, and heat resistance, among the benzene rings bonded to the amine group, p=2 and R are particularly preferred. The substitution positions are two ortho positions relative to the amine group.
前述式(5)所示之胺化合物之軟化點較佳為120℃以下,更佳為110℃以下。若軟化點為120℃以下,則衍生成前述式(1)所示之順丁烯二醯亞胺化合物時的黏度變低。藉此,容易確保硬化性樹脂組成物之流動性,不會損害對於玻璃布和碳纖維等纖維狀材料的浸漬性,且容易進行預浸體化等而使硬化性樹脂組成物成為半硬化狀態(B階段化)。雖亦可藉由增加稀釋溶劑而降低硬化性樹脂組成物之黏度,惟在此情況下,浸漬步驟中之硬化性樹脂組成物可能無法充分地附著於纖維狀材料,因此,較佳係將前述式(5)所示之胺化合物之軟化點設為120℃以下。 The softening point of the amine compound represented by the aforementioned formula (5) is preferably 120°C or lower, more preferably 110°C or lower. If the softening point is 120° C. or lower, the viscosity when derived into the maleimide compound represented by the aforementioned formula (1) becomes low. Thereby, it is easy to ensure the fluidity of the curable resin composition without impairing the impregnability of fibrous materials such as glass cloth and carbon fiber, and it is easy to make the curable resin composition into a semi-cured state by making it into a prepreg or the like ( B stage). Although the viscosity of the curable resin composition can also be reduced by increasing the diluting solvent, in this case, the curable resin composition in the impregnation step may not be fully adhered to the fibrous material. Therefore, it is better to use the aforementioned The softening point of the amine compound represented by formula (5) is 120°C or lower.
前述式(5)所示之胺化合物,係例如可藉由在酸觸媒存在下使苯胺類與過量的二異丙烯基苯(或α,α,α',α'-四甲基苯二甲醇類)進行反應而獲得。此時,關於苯胺系化合物之取代基,較佳為未經取代、或具有碳數1至5之烷基,就分子量控制、溶劑溶解性、介電特性、低吸水性、耐熱性之觀點而言,更佳為未經取代、或在與胺基鍵結的苯環之鄰位具有2個碳數1至3之烷基。 The amine compound represented by the aforementioned formula (5) can be prepared, for example, by reacting anilines with excess diisopropenylbenzene (or α, α, α', α'-tetramethylbenzene) in the presence of an acid catalyst. Methanols) are obtained by reacting. In this case, the substituent of the aniline compound is preferably unsubstituted or an alkyl group having 1 to 5 carbon atoms from the viewpoint of molecular weight control, solvent solubility, dielectric properties, low water absorption, and heat resistance. In other words, it is more preferred to be unsubstituted or have two alkyl groups having 1 to 3 carbon atoms in the ortho position of the benzene ring bonded to the amine group.
合成時,就酸觸媒而言,除了可使用鹽酸、磷酸、硫酸、甲酸、對甲苯磺酸、甲磺酸等液體酸觸媒以外,還可使用氯化鋁、氯化鋅等路易斯酸、活性黏土、酸性黏土、白碳、沸石、氧化矽-氧化鋁等固體酸觸媒、酸性離子交換樹脂等。此等酸觸媒可單獨或併用二種以上。相對於屬於反應基質之二異丙烯基苯(或α,α,α',α'-四甲基苯二甲醇類)及苯胺類之重量的總和,酸觸媒之使用量為0.01至50重量%,較佳為0.1至35重量%。酸觸媒之使用量若過多則有使無用的廢棄物增加之虞,若過少則有反應進行變慢之虞。關於所使用的溶劑,可列舉例如甲苯、二甲苯等芳香族溶劑、環己烷、正己烷等脂肪族溶劑、二乙醚、二異丙醚等醚類、乙酸乙酯、乙酸丁酯等酯系溶劑、甲基異丁基酮、環戊酮等酮系溶劑等之 類的非水溶性溶劑,惟並非限定於此等者,可併用2種以上。此外,除了前述非水溶性溶劑以外,亦可併用非質子性極性溶劑。可列舉例如二甲基碸、二甲基亞碸、二甲基甲醯胺、二甲基乙醯胺、1,3-二甲基-2-咪唑啉酮、N-甲基吡咯啶酮等,可併用2種以上。在使用非質子性極性溶劑之情況下,較佳使用沸點高於併用的非水溶性溶劑者。反應溫度較佳為80至250℃,更佳為90至240℃,又更佳為100℃至230℃。若反應溫度過高則有引起無用的熱分解反應之可能性,若反應溫度過低則有反應無法充分地進行之虞。在使用α,α,α',α'-四甲基苯二甲醇類作為原料之情況、或使用含有水之酸觸媒之情況下,所生成的水和體系中的水係在升溫時一邊與溶劑共沸一邊從體系內除去。反應終止後,以鹼性水溶液等來中和酸觸媒後,在油層中加入非水溶性有機溶劑並重複進行水洗直到廢水呈中性為止,然後在加熱減壓下除去溶劑。在使用活性黏土或離子交換樹脂之情況下,係在反應終止後過濾反應液並除去酸觸媒。 During synthesis, in addition to liquid acid catalysts such as hydrochloric acid, phosphoric acid, sulfuric acid, formic acid, p-toluenesulfonic acid, and methanesulfonic acid, Lewis acids such as aluminum chloride and zinc chloride can also be used. Activated clay, acidic clay, white carbon, zeolite, silica-alumina and other solid acid catalysts, acidic ion exchange resin, etc. These acid catalysts may be used alone or in combination of two or more types. Relative to the total weight of diisopropenylbenzene (or α, α, α', α'-tetramethylbenzenedimethanols) and anilines belonging to the reaction matrix, the acid catalyst is used in an amount of 0.01 to 50 wt. %, preferably 0.1 to 35% by weight. If the amount of acid catalyst used is too much, there is a risk of increasing useless waste, and if it is too little, there is a risk of slowing down the reaction. Examples of solvents used include aromatic solvents such as toluene and xylene, aliphatic solvents such as cyclohexane and n-hexane, ethers such as diethyl ether and diisopropyl ether, and esters such as ethyl acetate and butyl acetate. Solvents, ketone solvents such as methyl isobutyl ketone, cyclopentanone, etc. Such non-water-soluble solvents are not limited to these, and two or more types may be used in combination. In addition to the above-mentioned water-insoluble solvent, an aprotic polar solvent may be used in combination. Examples include dimethylsulfuric acid, dimethylsulfuric acid, dimethylformamide, dimethylacetylamide, 1,3-dimethyl-2-imidazolinone, N-methylpyrrolidone, and the like. , two or more types can be used together. When using an aprotic polar solvent, it is preferable to use a water-insoluble solvent with a boiling point higher than that used in combination. The reaction temperature is preferably 80 to 250°C, more preferably 90 to 240°C, still more preferably 100 to 230°C. If the reaction temperature is too high, a useless thermal decomposition reaction may occur, and if the reaction temperature is too low, the reaction may not proceed sufficiently. When α,α,α',α'-tetramethylbenzenedimethanol is used as the raw material, or when an acid catalyst containing water is used, the water produced and the water in the system will be heated up while increasing the temperature. It is removed from the system while azeotroping with the solvent. After the reaction is terminated, the acid catalyst is neutralized with an alkaline aqueous solution, etc., then a water-insoluble organic solvent is added to the oil layer and water washing is repeated until the waste water becomes neutral, and then the solvent is removed under heating and reduced pressure. In the case of using activated clay or ion exchange resin, the reaction solution is filtered and the acid catalyst is removed after the reaction is terminated.
就前述苯胺類而言,可列舉例如苯胺、鄰甲苯胺、間甲苯胺、對甲苯胺、鄰乙苯胺、間乙苯胺、對乙苯胺、鄰丙苯胺、間丙苯胺、對丙苯胺、鄰異丙苯胺、間異丙苯胺、對異丙苯胺、2,6-二甲基苯胺、2,6-二乙基苯胺、2,6-二丙基苯胺、2,6-異丙苯胺、2-乙基-6-甲基苯胺、2-丙基-6-甲基苯胺、2-異丙基-6-甲基苯胺、2-乙基-6-丙基苯胺、2-乙基-6-異丙基苯胺等,惟並非限於此等者。可單獨使用此等、或併用2種以上。若碳數多則溶劑溶解性會提升,但耐熱性會降低,故較佳為未經取代或經碳數1至3之烷基取代者,更佳為未經取代或經碳數1至2之烷基取代者,最佳為未經取代或經甲基取代者。 Examples of the anilines include aniline, o-toluidine, m-toluidine, p-toluidine, o-ethylaniline, m-ethylaniline, p-ethylaniline, o-propylaniline, m-propylaniline, p-propylaniline, o-isopropylaniline Propylaniline, m-isopropylaniline, p-isopropylaniline, 2,6-dimethylaniline, 2,6-diethylaniline, 2,6-dipropylaniline, 2,6-isopropylaniline, 2- Ethyl-6-methylaniline, 2-propyl-6-methylaniline, 2-isopropyl-6-methylaniline, 2-ethyl-6-propylaniline, 2-ethyl-6- Isopropylaniline, etc., but are not limited to these. These can be used individually or in combination of 2 or more types. If the carbon number is large, the solvent solubility will be improved, but the heat resistance will be reduced, so it is preferably unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms, and more preferably unsubstituted or substituted with an alkyl group having 1 to 2 carbon atoms. The alkyl substituted ones are preferably unsubstituted or methyl substituted.
前述二異丙烯基苯而言可列舉例如:1,2-二異丙基苯、1,3-二異丙基苯、1,4-二異丙基苯、及此等之烷基取代體等。 Examples of the aforementioned diisopropenylbenzene include: 1,2-diisopropylbenzene, 1,3-diisopropylbenzene, 1,4-diisopropylbenzene, and alkyl substituted products thereof. wait.
前述α,α,α',α'-四甲基苯二甲醇類可列舉例如:α,α,α',α'-四甲基-1,2-苯二甲醇、α,α,α',α'-四甲基-1,3-苯二甲醇、α,α,α',α'-四甲基-1,4-苯二甲醇、及此等之烷基取代體等。 Examples of the aforementioned α,α,α',α'-tetramethylbenzenedimethanol include: α,α,α',α'-tetramethyl-1,2-benzenedimethanol, α,α,α' , α'-tetramethyl-1,3-benzenedimethanol, α,α,α',α'-tetramethyl-1,4-benzenedimethanol, and alkyl substitutes thereof, etc.
前述二異丙烯基苯及前述α,α,α',α'-四甲基苯二甲醇類可分別單獨使用、或併用2種以上。相對於苯胺類之胺基1莫耳,此等之使用量較佳為1.0至10倍莫耳、更較佳為1.0至7.5倍莫耳,又更佳為1.0至5.0倍莫耳。 The aforementioned diisopropenylbenzene and the aforementioned α, α, α′, α′-tetramethylbenzenedimethanols may be used individually, or two or more types may be used in combination. The usage amount is preferably 1.0 to 10 times mole, more preferably 1.0 to 7.5 times mole, and still more preferably 1.0 to 5.0 times mole relative to 1 mole of amine group of aniline.
〔聚合起始劑〕 [Polymerization initiator]
本實施型態之硬化性樹脂組成物,亦可藉由添加聚合起始劑而提升硬化性。就聚合起始劑而言,其為能使乙烯性不飽和鍵等烯烴官能基進行聚合的化合物,可列舉如烯烴複分解(Olefin metathesis)聚合起始劑、陰離子聚合起始劑、陽離子聚合起始劑及自由基聚合起始劑。其中,較佳係使用具有硬化性及適度穩定性的自由基聚合起始劑。若為以鉬為中心金屬的Schrock觸媒等烯烴複分解聚合起始劑、正丁基鋰(n-BuLi)等陰離子聚合起始劑、和三乙基鋁等陽離子聚合起始劑時,會發生與空氣中的水分進行反應等狀況而使穩定性差。 The curable resin composition of this embodiment can also be enhanced in curability by adding a polymerization initiator. The polymerization initiator is a compound that can polymerize olefin functional groups such as ethylenically unsaturated bonds, and examples thereof include olefin metathesis polymerization initiators, anionic polymerization initiators, and cationic polymerization initiators. agent and free radical polymerization initiator. Among them, it is preferable to use a radical polymerization initiator having curability and moderate stability. This may occur if it is an olefin metathesis polymerization initiator such as a Schrock catalyst with molybdenum as the central metal, an anionic polymerization initiator such as n-butyllithium (n-BuLi), or a cationic polymerization initiator such as triethylaluminum. Reacts with moisture in the air, resulting in poor stability.
就自由基聚合起始劑而言,係意指藉由紫外線或可見光之照射或加熱而產生的自由基並起始鏈聚合反應的化合物。關於可使用的自由基聚合起始劑,可列舉如有機過氧化物、偶氮系化合物、四苯-1,2-乙二醇(Benzopinacol)類等,就硬化溫度之控制或脫氣之抑制、對分解物之電氣特性的影響小之觀點而言,較佳係使用有機過氧化物。 The free radical polymerization initiator refers to a compound that generates free radicals by irradiation or heating with ultraviolet or visible light and initiates a chain polymerization reaction. Examples of free radical polymerization initiators that can be used include organic peroxides, azo compounds, tetraphenyl-1,2-ethylene glycols (Benzopinacol), etc., for controlling the curing temperature or suppressing degassing. , from the viewpoint of having little impact on the electrical properties of decomposed products, it is better to use organic peroxides.
就上述有機過氧化物而言,可列舉例如過氧化甲基乙基酮、過氧化乙醯丙基酮等過氧化酮類、過氧化苯甲醯等過氧化二醯基類、過氧化二異丙苯、1,3-雙-(三級丁基過氧異丙基)-苯等過氧化二烷基類、過氧化苯甲酸三級丁酯、1,1-二-三級 丁基過氧環己烷等過氧化縮酮類、α-過氧化新癸酸異丙苯酯、過氧化新癸酸三級丁酯、過氧化新戊酸三級丁酯、過氧化-2-乙基己酸1,1,3,3-四甲基丁酯、過氧化-2-乙基己酸三級戊酯、過氧化-2-乙基己酸三級丁酯、過氧化-3,5,5-三甲基己酸三級戊酯、過氧化-3,5,5-三甲基己酸三級丁酯、過氧化苯甲酸三級戊酯等烷基過氧化酯類、過氧化二碳酸二-2-乙基己酯、過氧化二碳酸雙(4-三級丁基環己基)酯、過氧化異丙基碳酸三級丁酯、1,6-雙(三級丁基過氧羰氧基)正己烷等過氧化碳酸酯類、三級丁基氫過氧化物、異丙苯氫過氧化物、過氧化辛酸三級丁酯、過氧化月桂醯基等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。上述有機過氧化物之中,較佳為過氧化酮類、過氧化二醯基類、過氧化氫物類、過氧化二烷基類、過氧化縮酮類、烷基過氧化酯類、過氧化碳酸酯類等,更佳為過氧化二烷基類。 Examples of the above-mentioned organic peroxides include peroxyketones such as methyl ethyl ketone peroxide and acetyl propyl ketone peroxide, diyl peroxides such as benzoyl peroxide, and diisoperoxides. Propylbenzene, 1,3-bis-(tertiary butylperoxyisopropyl)-benzene and other dialkyl peroxides, tertiary butyl peroxybenzoate, 1,1-di-tertiary Peroxyketals such as butyl peroxycyclohexane, α-cumyl peroxyneodecanoate, tertiary butyl peroxyneodecanoate, tertiary butyl peroxypivalate, peroxy-2 -1,1,3,3-tetramethylbutyl ethylhexanoate, tertiary amyl peroxy-2-ethylhexanoate, tertiary butyl peroxy-2-ethylhexanoate, peroxy- Alkyl peroxyesters such as tertiary amyl peroxy-3,5,5-trimethylhexanoate, tertiary butyl peroxy-3,5,5-trimethylhexanoate, tertiary amyl peroxybenzoate, etc. , di-2-ethylhexyl peroxydicarbonate, bis(4-tertiary butylcyclohexyl) peroxydicarbonate, tertiary butyl peroxyisopropyl carbonate, 1,6-bis(tertiary) Butyl peroxycarbonyloxy) n-hexane and other peroxycarbonates, tertiary butyl hydroperoxide, cumene hydroperoxide, tertiary butyl peroxyoctanoate, lauryl peroxide, etc., but It is not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used. Among the above-mentioned organic peroxides, preferred are ketone peroxides, diyl peroxides, hydrogen peroxides, dialkyl peroxides, ketal peroxides, alkyl peroxyesters, and peroxyesters. Oxidized carbonates, etc., more preferably dialkyl peroxides.
上述偶氮系化合物可列舉例如偶氮二異丁腈、4,4’-偶氮雙(4-氰基戊酸)、2,2’-偶氮雙(2,4-二甲基戊腈)等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 Examples of the above-mentioned azo compounds include azobisisobutyronitrile, 4,4'-azobis(4-cyanovaleric acid), and 2,2'-azobis(2,4-dimethylvaleronitrile). ), etc., but are not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used.
關於聚合起始劑之添加量,在將硬化性樹脂組成物中排除無機填充劑(填料)後之不揮發分的合計設為100質量份之情況下,較佳為0.01至5質量份,特佳為0.01至3質量份。若所使用的聚合起始劑之量未達0.01質量份,則在聚合反應時有分子量無法充分伸長之虞,若多於5質量份,則有損害介電常數、介電正切等介電特性之虞。 The amount of the polymerization initiator to be added is preferably 0.01 to 5 parts by mass when the total amount of non-volatile matter excluding the inorganic filler (filler) in the curable resin composition is 100 parts by mass. Preferably, it is 0.01 to 3 parts by mass. If the amount of the polymerization initiator used is less than 0.01 parts by mass, the molecular weight may not be fully elongated during the polymerization reaction. If it is more than 5 parts by mass, the dielectric properties such as dielectric constant and dielectric tangent may be impaired. The danger.
〔阻聚劑〕 [Polymerization inhibitor]
本實施型態之硬化性樹脂組成物可含有阻聚劑。藉由含有阻聚劑,可提升保管穩定性,並可控制反應起始溫度。藉由控制反應起始溫度,而容易確保硬化性 樹脂組成物之流動性,不會損害玻璃布或碳纖維等纖維狀材料的浸漬性,且容易進行預浸體化等B階段化。在預浸體化時,若聚合反應過度進行,則在積層步驟中容易發生難以積層等之問題。 The curable resin composition of this embodiment may contain a polymerization inhibitor. By containing a polymerization inhibitor, the storage stability can be improved and the reaction starting temperature can be controlled. Hardening is easily ensured by controlling the reaction starting temperature The fluidity of the resin composition does not impair the impregnability of fibrous materials such as glass cloth or carbon fiber, and facilitates B-stage transformation such as prepreg formation. If the polymerization reaction proceeds excessively during the preparation of prepregs, problems such as difficulty in lamination during the lamination step may easily occur.
阻聚劑可在合成前述式(1)所示之化合物時添加,亦可在合成後添加。相對於前述式(1)所示之化合物100重量份,阻聚劑之使用量為0.008至1重量份,較佳為0.01至0.5重量份。 The polymerization inhibitor can be added when synthesizing the compound represented by the aforementioned formula (1), or can be added after synthesis. The usage amount of the polymerization inhibitor is 0.008 to 1 part by weight, preferably 0.01 to 0.5 part by weight relative to 100 parts by weight of the compound represented by the aforementioned formula (1).
阻聚劑可列舉例如酚系、硫系、磷系、受阻胺系、亞硝基系、硝醯基自由基系之阻聚劑。此外,阻聚劑可使用1種,亦可併用複數種。此等之中,在本實施型態中,較佳為酚系、受阻胺系、亞硝基系、硝醯基自由基系之阻聚劑。 Examples of polymerization inhibitors include phenol-based, sulfur-based, phosphorus-based, hindered amine-based, nitroso-based, and nitryl radical-based polymerization inhibitors. In addition, a single type of polymerization inhibitor may be used, or a plurality of types may be used in combination. Among these, in this embodiment, a phenol-based, hindered amine-based, nitroso-based, or nitryl radical-based polymerization inhibitor is preferred.
上述酚系阻聚劑可列舉例如2,6-二-三級丁基對甲酚、丁基化羥基苯甲醚、2,6-二-三級丁基對乙酚、β-(3,5-二-三級丁基-4-羥基苯基)丙酸硬脂酯、3-(3,5-二-三級丁基-4-羥基苯基)丙酸異辛酯、2,4-雙-(正辛硫基)-6-(4-羥基-3,5-二-三級丁基苯胺)-1,3,5-三、2,4-雙[(辛硫基)甲基]鄰甲酚等單酚類,2,2’-亞甲基雙(4-甲基-6-三級丁基酚)、2,2’-亞甲基雙(4-乙基-6-三級丁基酚)、4,4’-硫基雙(3-甲基-6-三級丁基酚)、4,4’-亞丁基雙(3-甲基-6-三級丁基酚)、三乙二醇-雙[3-(3-三級丁基-5-甲基-4-羥基苯基)丙酸酯]、1,6-正己烷二醇-雙[3-(3,5-二-三級丁基-4-羥基苯基)丙酸酯]、N,N’-六亞甲基雙(3,5-二-三級丁基-4-羥基-氫化肉桂醯胺)、2,2-硫基-二乙烯雙[3-(3,5-二-三級丁基-4-羥基苯基)丙酸酯]、3,5-二-三級丁基-4-羥基苄基膦酸-二乙基酯、3,9-雙[1,1-二甲基-2-{β-(3-三級丁基-4-羥基-5-甲基苯基)丙醯氧基}乙基]2,4,8,10-四氧雜螺[5,5]十一烷、雙(3,5-二-三級丁基-4-羥基苄基磺酸乙基)鈣等雙酚類,1,1,3-參(2-甲基-4-羥基-5-三級丁基苯基)丁烷、1,3,5-三甲基- 2,4,6-參(3,5-二-三級丁基-4-羥基苄基)苯、肆-[亞甲基-3-(3’,5’-二-三級丁基-4’-羥基苯基)丙酸酯]甲烷、雙[3,3’-雙-(4’-羥基-3’-三級丁基苯基)丁酸]乙二醇酯、參-(3,5-二-三級丁基-4-羥基苄基)-異氰脲酸酯、1,3,5-參(3’,5’-二-三級丁基-4’-羥基苄基)-S-三-2,4,6-(1H,3H,5H)三酮、生育酚等高分子型酚類等,惟並非限於此等者。 Examples of the phenolic polymerization inhibitor include 2,6-di-tertiary butyl-p-cresol, butylated hydroxyanisole, 2,6-di-tertiary butyl-p-ethylphenol, β-(3, 5-Di-tertiary butyl-4-hydroxyphenyl)stearyl propionate, 3-(3,5-di-tertiary butyl-4-hydroxyphenyl) isooctyl propionate, 2,4 -Bis-(n-octylthio)-6-(4-hydroxy-3,5-di-tertiary butylaniline)-1,3,5-tertiary , 2,4-bis[(octylthio)methyl]o-cresol and other monophenols, 2,2'-methylenebis(4-methyl-6-tertiary butylphenol), 2,2 '-Methylenebis(4-ethyl-6-tertiary butylphenol), 4,4'-Thiobis(3-methyl-6-tertiary butylphenol), 4,4'-ethylene Bis(3-methyl-6-tertiary butylphenol), triethylene glycol-bis[3-(3-tertiary butyl-5-methyl-4-hydroxyphenyl)propionate], 1,6-n-hexanediol-bis[3-(3,5-di-tertiary butyl-4-hydroxyphenyl)propionate], N,N'-hexamethylene bis(3,5 -Di-tertiary butyl-4-hydroxy-hydrocinnamamide), 2,2-thio-diethylenebis[3-(3,5-di-tertiary butyl-4-hydroxyphenyl)propanol acid ester], 3,5-di-tertiary butyl-4-hydroxybenzylphosphonic acid-diethyl ester, 3,9-bis[1,1-dimethyl-2-{β-(3- Tertiary butyl-4-hydroxy-5-methylphenyl)propyloxy}ethyl]2,4,8,10-tetraxaspiro[5,5]undecane, bis(3,5 -Di-tertiary butyl-4-hydroxybenzyl sulfonate ethyl) calcium and other bisphenols, 1,1,3-gin (2-methyl-4-hydroxy-5-tertiary butylphenyl) Butane, 1,3,5-trimethyl-2,4,6-shen(3,5-di-tertiary butyl-4-hydroxybenzyl)benzene, 4-[methylene-3-( 3',5'-Di-tertiary butyl-4'-hydroxyphenyl)propionate]methane, bis[3,3'-bis-(4'-hydroxy-3'-tertiary butylphenyl )butyric acid] ethylene glycol ester, gin-(3,5-di-tertiary butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-gin(3',5'- Di-tertiary butyl-4'-hydroxybenzyl)-S-tri -2,4,6-(1H,3H,5H)triketone, tocopherol and other high molecular phenols, but not limited to these.
上述硫系阻聚劑可列舉例如3,3’-硫基二丙酸二月桂酯、3,3’-硫基二丙酸二肉荳蔻酯、3,3’-硫基二丙酸二硬脂酯等,惟並非限於此等者。 Examples of the sulfur-based polymerization inhibitor include dilauryl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate, and disulfide 3,3'-thiodipropionate. Fatty esters, etc., but not limited to these.
上述磷系阻聚劑可列舉例如三苯基亞磷酸酯、二苯基異癸基亞磷酸酯、苯基二異癸基亞磷酸酯、參(壬基苯基)亞磷酸酯、二異癸基新戊四醇亞磷酸酯、參(2,4-二-三級丁基苯基)亞磷酸酯、環狀新戊烷四醯雙(十八基)亞磷酸酯、環狀新戊烷四醯雙(2,4-二-三級丁基苯基)亞磷酸酯、環狀新戊烷四醯雙(2,4-二-三級丁基-4-甲基苯基)亞磷酸酯、雙[2-三級丁基-6-甲基-4-{2-(十八基氧基羰基)乙基}苯基]氫亞磷酸酯等亞磷酸酯類、9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-(3,5-二-三級丁基-4-羥基苄基)-9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-癸氧基-9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物等氧雜磷雜菲氧化物類等,惟並非限於此等者。 Examples of the phosphorus-based polymerization inhibitor include triphenyl phosphite, diphenyl isodecyl phosphite, phenyl diisodecyl phosphite, nonyl phenyl phosphite, and diisodecyl phosphite. Neopentyl erythritol phosphite, 2,4-di-tertiary butylphenyl phosphite, cyclic neopentane tetrakis(octadecyl) phosphite, cyclic neopentane Tetrakis(2,4-di-tertiary butylphenyl)phosphite, cyclic neopentane tetrabis(2,4-di-tertiary butyl-4-methylphenyl)phosphite Phosphites such as esters, bis[2-tertiary butyl-6-methyl-4-{2-(octadecyloxycarbonyl)ethyl}phenyl]hydrophosphite, 9,10-di Hydrogen-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(3,5-di-tertiary butyl-4-hydroxybenzyl)-9,10-dihydro-9-oxa -10-Phosphaphenanthrene-10-oxide, 10-decyloxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and other oxaphosphaphenanthrene oxides, etc. , but it is not limited to these.
上述受阻胺系阻聚劑可列舉例如Adekastab LA-40MP、Adekastab LA-40Si、Adekastab LA-402AF、Adekastab LA-87、Adekastab LA-82、Adekastab LA-81、Adekastab LA-77Y、Adekastab LA-77G、Adekastab LA-72、Adekastab LA-68、Adekastab LA-63P、Adekastab LA-57、Adekastab LA-52、Chimassorb2020FDL、Chimassorb944FDL、Chimassorb944LD、Tinuvin622SF、TinuvinPA144、 Tinuvin765、Tinuvin770DF、TinuvinXT55FB、Tinuvin111FDL、Tinuvin783FDL、Tinuvin791FB等,惟並非限於此等者。 Examples of the hindered amine polymerization inhibitor include Adekastab LA-40MP, Adekastab LA-40Si, Adekastab LA-402AF, Adekastab LA-87, Adekastab LA-82, Adekastab LA-81, Adekastab LA-77Y, Adekastab LA-77G, Adekastab LA-72, Adekastab LA-68, Adekastab LA-63P, Adekastab LA-57, Adekastab LA-52, Chimassorb2020FDL, Chimassorb944FDL, Chimassorb944LD, Tinuvin622SF, TinuvinPA144, Tinuvin765, Tinuvin770DF, TinuvinXT55FB, Tinuvin111FDL, Tinuvin783FDL, Tinuvin791FB, etc., but are not limited to these.
上述亞硝基系阻聚劑可列舉例如對亞硝基酚、N-亞硝基二苯基胺、N-亞硝基苯基羥基胺之銨鹽(銅鐵靈(cupferron))等,惟並非限於此等者。此等之中,較佳為N-亞硝基苯基羥基胺之銨鹽(銅鐵靈)。 Examples of the nitroso-based polymerization inhibitor include p-nitrosophenol, N-nitrosodiphenylamine, ammonium salt of N-nitrosophenylhydroxylamine (cupferron), etc. It is not limited to these. Among these, the ammonium salt of N-nitrosophenylhydroxylamine (cupferrite) is preferred.
上述硝醯基自由基系阻聚劑可列舉例如:二-三級丁基氮氧化物、2,2,6,6-四甲基哌啶-1-氧化物、4-羥基-2,2,6,6-四甲基哌啶-1-氧化物、4-側氧基-2,2,6,6-四甲基哌啶-1-氧化物、4-胺基-2,2,6,6-四甲基哌啶-1-氧化物、4-甲氧基-2,2,6,6-四甲基哌啶-1-氧化物、4-乙醯氧基-2,2,6,6-四甲基哌啶-1-氧化物、4-苯甲醯氧基-2,2,6,6-四甲基哌啶-1-氧化物等,惟並非限於此等者。 Examples of the nitroxyl radical polymerization inhibitor include di-tertiary butyl nitrogen oxide, 2,2,6,6-tetramethylpiperidine-1-oxide, and 4-hydroxy-2,2 ,6,6-tetramethylpiperidine-1-oxide, 4-side oxy-2,2,6,6-tetramethylpiperidine-1-oxide, 4-amino-2,2, 6,6-Tetramethylpiperidine-1-oxide, 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxide, 4-acetyloxy-2,2 ,6,6-tetramethylpiperidine-1-oxide, 4-benzyloxy-2,2,6,6-tetramethylpiperidine-1-oxide, etc., but are not limited to these .
〔無機填充劑〕 [Inorganic filler]
本實施型態之硬化性樹脂組成物可含有無機填充劑。無機填充劑可列舉例如熔融二氧化矽、結晶二氧化矽、多孔質二氧化矽、氧化鋁、鋯石、矽酸鈣、碳酸鈣、石英粉、碳化矽、氮化矽、氮化硼、氧化鋯、氮化鋁、石墨、鎂橄欖石(forsterite)、塊滑石(steatite)、尖晶石、莫來石、二氧化鈦、滑石、黏土、氧化鐵石棉、玻璃粉等粉末、或將此等製成球形狀或粉碎後的無機填料等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 The curable resin composition of this embodiment may contain an inorganic filler. Examples of the inorganic filler include fused silica, crystalline silica, porous silica, alumina, zircon, calcium silicate, calcium carbonate, quartz powder, silicon carbide, silicon nitride, boron nitride, oxide Zirconium, aluminum nitride, graphite, forsterite, steatite, spinel, mullite, titanium dioxide, talc, clay, iron oxide asbestos, glass powder and other powders, or made of these Spherical shapes or pulverized inorganic fillers, etc., but are not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used.
在獲得用以密封半導體之硬化性樹脂組成物之情況下,於硬化性樹脂組成物100質量份中,無機填充材之使用量較佳為80至92質量份,更佳為83至90質量份。此外,在獲得層間絕緣層形成材料、覆銅積層板或預浸體、RCC等基板材料用之硬化性樹脂組成物之情況下,於硬化性樹脂組成物100質量份中,上述無機填充材之使用量較佳為5至80質量份,更佳為10至60質量份。 When obtaining a curable resin composition for sealing a semiconductor, the usage amount of the inorganic filler is preferably 80 to 92 parts by mass, and more preferably 83 to 90 parts by mass in 100 parts by mass of the curable resin composition. . In addition, when obtaining a curable resin composition for interlayer insulating layer forming materials, copper-clad laminates or prepregs, RCC and other substrate materials, in 100 parts by mass of the curable resin composition, one of the above-mentioned inorganic fillers The usage amount is preferably 5 to 80 parts by mass, more preferably 10 to 60 parts by mass.
〔硬化促進劑〕 [Harding accelerator]
本實施型態之硬化性樹脂組成物可藉由添加硬化促進劑而提升硬化性。就硬化促進劑而言,較佳係藉由紫外線和可見光之照射或加熱而產生陰離子以促進硬化反應的陰離子系硬化促進劑、或者是藉由紫外線或可見光之照射或加熱而產生陽離子以促進硬化反應的陽離子系硬化促進劑。 The curable resin composition of this embodiment can improve curability by adding a curing accelerator. The hardening accelerator is preferably an anionic hardening accelerator that generates anions by irradiation or heating of ultraviolet or visible light to accelerate the curing reaction, or an anionic curing accelerator that generates cations by irradiation or heating of ultraviolet or visible light to accelerate hardening. Reactive cationic hardening accelerator.
陰離子系硬化促進劑可列舉例如2-甲基咪唑、2-乙基咪唑、2-乙基-4-甲基咪唑等咪唑類、三乙基胺、三丁基胺等三烷基胺、4-二甲基胺基吡啶、苄基二甲基胺、2,4,6,-參(二甲基胺基甲基)酚、1,8-二氮雜雙環(5,4,0)-十一碳烯等,較佳為4-二甲基胺基吡啶、1,8-二氮雜雙環(5,4,0)-十一碳烯。此外,可列舉如三苯基膦等膦類、四丁基銨鹽、三異丙基甲基銨鹽、三甲基癸基銨鹽、十六基三甲基銨鹽、十六烷基三甲基氫氧化銨等4級銨鹽等。 Examples of the anionic hardening accelerator include imidazoles such as 2-methylimidazole, 2-ethylimidazole, and 2-ethyl-4-methylimidazole; trialkylamines such as triethylamine and tributylamine; 4 -Dimethylaminopyridine, benzyldimethylamine, 2,4,6,-shen(dimethylaminomethyl)phenol, 1,8-diazabicyclo(5,4,0)- Undecene and the like, preferably 4-dimethylaminopyridine and 1,8-diazabicyclo(5,4,0)-undecene. In addition, phosphines such as triphenylphosphine, tetrabutylammonium salt, triisopropylmethylammonium salt, trimethyldecyl ammonium salt, hexadecyltrimethylammonium salt, cetyltrimethylammonium salt, etc. can be cited. Methyl ammonium hydroxide and other 4th grade ammonium salts.
陽離子系硬化促進劑可列舉例如三苯基苄基鏻鹽、三苯基乙基鏻鹽、四丁基鏻鹽等4級鏻鹽(4級鹽之相對離子為鹵素、有機酸根離子、氫氧根離子等,雖無特別指定,惟特佳為有機酸根離子、氫氧根離子)、辛酸錫、羧酸鋅(2-乙基正己烷酸鋅、硬脂酸鋅、二十二酸鋅、肉豆蔻酸鋅)、磷酸酯鋅(辛基磷酸鋅、硬脂醇磷酸鋅)等過度金屬化合物(過度金屬鹽)等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 Examples of cationic hardening accelerators include 4th-level phosphonium salts such as triphenylbenzylphosphonium salt, triphenylethylphosphonium salt, and tetrabutylphosphonium salt (the counter ions of the 4th-level salt are halogen, organic acid ions, and hydroxide Although not specifically designated, organic acid ions, hydroxide ions, etc. are particularly preferred, tin octoate, zinc carboxylate (zinc 2-ethyl n-hexanoate, zinc stearate, zinc behenate, Transition metal compounds (transition metal salts) such as zinc myristate), zinc phosphate esters (zinc octyl phosphate, zinc stearyl phosphate), etc., but are not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used.
相對於硬化性樹脂組成物中排除無機填充劑(填料)後之不揮發分的合計100質量份,硬化促進劑之調配量係因應需要而使用0.01至5.0質量份。 The compounding amount of the hardening accelerator is 0.01 to 5.0 parts by mass based on necessity, relative to 100 parts by mass of the total non-volatile matter excluding inorganic fillers (fillers) in the curable resin composition.
〔阻燃劑〕 [Flame retardant]
本實施型態之硬化性樹脂組成物可使用阻燃劑。阻燃劑可列舉例如鹵素系阻燃劑、無機系阻燃劑(銻化合物、金屬氫氧化物、氮化合物、硼化合物等)、磷系阻燃劑等,惟就達成無鹵素阻燃性之觀點而言,較佳為磷系阻燃劑。 The curable resin composition of this embodiment may use a flame retardant. Examples of flame retardants include halogen-based flame retardants, inorganic flame retardants (antimony compounds, metal hydroxides, nitrogen compounds, boron compounds, etc.), phosphorus-based flame retardants, etc. To achieve halogen-free flame retardancy, From a viewpoint, a phosphorus-based flame retardant is preferable.
上述磷系阻燃劑可為反應型或添加型。具體例可列舉如磷酸三甲酯、磷酸三乙酯、磷酸三甲苯酯、磷酸三(二甲苯基)酯、甲酚二苯基磷酸酯、甲酚-二-2,6-二甲苯基磷酸酯、1,3-伸苯基雙(磷酸二(二甲苯基)酯)、1,4-伸苯基雙(磷酸二(二甲苯基)酯)、4,4’-聯苯(磷酸二(二甲苯基)酯)等磷酸酯類、9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10(2,5-二羥基苯基)-10H-9-氧雜-10-磷雜菲-10-氧化物等磷烷類、及使環氧樹脂與前述磷烷類之活性氫進行反應而得的含磷之環氧化合物、赤磷等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。上述例示物質之中,較佳為磷酸酯類、磷烷類或含磷之環氧化合物,特佳為1,3-伸苯基雙(磷酸二(二甲苯基)酯)、1,4-伸苯基雙(磷酸二(二甲苯基)酯)、4,4’-聯苯(磷酸二(二甲苯基)酯)、或含磷之環氧化合物。 The above-mentioned phosphorus-based flame retardant may be a reactive type or an additive type. Specific examples include trimethyl phosphate, triethyl phosphate, tricresyl phosphate, tris(xylyl)phosphate, cresol diphenyl phosphate, and cresol-di-2,6-xylyl phosphate. Ester, 1,3-phenylenebis(di(dylyl)phosphate), 1,4-phenylenebis(di(dylyl)phosphate), 4,4'-biphenyl(di(dimethylphenyl)phosphate) (xylyl)ester) and other phosphates, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10(2,5-dihydroxyphenyl)-10H-9 - Phosphanes such as oxa-10-phosphaphenanthrene-10-oxide, and phosphorus-containing epoxy compounds obtained by reacting epoxy resin with the active hydrogen of the aforementioned phosphoranes, red phosphorus, etc., but not Limited to these. In addition, one type of these systems may be used, or a plurality of types may be used. Among the above-mentioned exemplified substances, phosphates, phosphanes, or phosphorus-containing epoxy compounds are preferred, and 1,3-phenylenebis(di(xylyl)phosphate), 1,4- Phenylene bis(di(xylyl)phosphate), 4,4'-biphenyl(di(dylyl)phosphate), or phosphorus-containing epoxy compounds.
在將硬化性樹脂組成物中排除無機填充劑(填料)後之不揮發分的合計設為100質量份之情況下,阻燃劑之含量較佳為0.1至0.6質量份之範圍。若未達0.1質量份則有阻燃性變不充分之虞,若多於0.6質量份則有硬化物之吸濕性、介電特性受到不良影響之虞。 When the total amount of non-volatile matter excluding inorganic fillers (fillers) in the curable resin composition is 100 parts by mass, the content of the flame retardant is preferably in the range of 0.1 to 0.6 parts by mass. If it is less than 0.1 parts by mass, the flame retardancy may become insufficient. If it exceeds 0.6 parts by mass, the hygroscopicity and dielectric properties of the cured material may be adversely affected.
〔光穩定劑〕 [Light stabilizer]
本實施型態之硬化性樹脂組成物可使用光穩定劑。就光穩定劑而言,適宜為受阻胺系之光穩定劑,尤其適宜為HALS(受阻胺系光穩定劑,Hindered Amine Light Stabilizers)等。HALS可列舉例如二丁基胺/1,3,5-三/N,N’-雙(2,2,6,6-四甲基-4-哌啶基-1,6-六亞甲基二胺與N-(2,2,6,6-四甲基-4-哌啶基)丁基胺之反應物、 丁二酸二甲基-1-(2-羥基乙基)-4-羥基-2,2,6,6-四甲基哌啶反應物、聚[{6-(1,1,3,3-四甲基丁基)胺基-1,3,5-三-2,4-二基}{(2,2,6,6-四甲基-4-哌啶基)亞胺基}六亞甲基{(2,2,6,6-四甲基-4-哌啶基)亞胺基}]、雙(1,2,2,6,6-五甲基-4-哌啶基)[[3,5-雙(1,1-二甲基乙基)-4-羥基苯基]甲基]丙二酸丁酯、雙(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、雙(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、雙(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、雙(1,2,2,6,6-五甲基-4-哌啶基)2-(3,5-二-三級丁基-4-羥基苄基)-2-正丁基丙二酸酯等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 The curable resin composition of this embodiment may use a light stabilizer. As the light stabilizer, hindered amine light stabilizers are suitable, and HALS (Hindered Amine Light Stabilizers) and the like are particularly suitable. Examples of HALS include dibutylamine/1,3,5-tris /N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl-1,6-hexamethylenediamine and N-(2,2,6,6-tetramethyl Reaction of dimethyl-1-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidine succinate Material, poly[{6-(1,1,3,3-tetramethylbutyl)amino-1,3,5-tri -2,4-diyl}{(2,2,6,6-tetramethyl-4-piperidinyl)imino}hexamethylene{(2,2,6,6-tetramethyl- 4-piperidinyl)imino}], bis(1,2,2,6,6-pentamethyl-4-piperidinyl)[[3,5-bis(1,1-dimethylethyl methyl)-4-hydroxyphenyl]methyl]butyl malonate, bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis(1,2,2 ,6,6-pentamethyl-4-piperidyl) sebacate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate , bis(1,2,2,6,6-pentamethyl-4-piperidinyl)2-(3,5-di-tertiary butyl-4-hydroxybenzyl)-2-n-butylpropanyl Diacid esters, etc., but are not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used.
在將硬化性樹脂組成物中排除無機填充劑(填料)後之不揮發分的合計設為100質量份之情況下,光穩定劑之含量較佳為0.001至10質量份之範圍。若未達0.001質量份則有無法充分發揮光穩定效果之虞,若多於10質量份則有使硬化物之吸濕性、介電特性受到不良影響之虞。 When the total amount of nonvolatile matter excluding inorganic fillers (fillers) in the curable resin composition is 100 parts by mass, the content of the light stabilizer is preferably in the range of 0.001 to 10 parts by mass. If it is less than 0.001 parts by mass, the light stabilizing effect may not be fully exerted. If it is more than 10 parts by mass, the hygroscopicity and dielectric properties of the cured material may be adversely affected.
〔黏結劑樹脂〕 [Binder resin]
本實施型態之硬化性樹脂組成物可使用黏結劑樹脂。黏結劑樹脂可列舉例如丁縮醛系樹脂、乙縮醛系樹脂、丙烯酸系樹脂、環氧-耐綸系樹脂、NBR-酚系樹脂、環氧-NBR系樹脂、聚矽氧(silicone)系樹脂等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 The curable resin composition of this embodiment may use a binder resin. Examples of the binder resin include butyral resin, acetal resin, acrylic resin, epoxy-nylon resin, NBR-phenol resin, epoxy-NBR resin, and silicone resin. Resin, etc., but are not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used.
黏結劑樹脂之調配量,較佳為不損害硬化物之阻燃性、耐熱性的範圍,若在將硬化性樹脂組成物中排除無機填充劑(填料)後之不揮發分的合計設為100質量份之情況下,較佳為0.05至50質量份,更佳為0.05至20質量份。 The blending amount of the binder resin is preferably within a range that does not impair the flame retardancy and heat resistance of the cured product. If the total non-volatile content of the cured resin composition is 100 after excluding the inorganic filler (filler) In the case of parts by mass, it is preferably 0.05 to 50 parts by mass, more preferably 0.05 to 20 parts by mass.
〔添加劑〕 [Additive]
本實施型態之硬化性樹脂組成物可使用添加劑。添加劑可列舉例如丙烯腈共聚物之改質物、聚乙烯、氟樹脂、聚矽氧凝膠、聚矽氧油、矽烷偶合劑等填充材的表面處理劑、脫模劑、碳黑、酞青藍、酞青綠等著色劑。 The curable resin composition of this embodiment may use additives. Examples of additives include modified products of acrylonitrile copolymer, surface treatment agents for fillers such as polyethylene, fluororesin, polysilicone gel, polysilicone oil, and silane coupling agents, release agents, carbon black, and phthalocyanine blue. , phthalocyanine green and other colorants.
相對於硬化性樹脂組成物100質量份,添加劑之調配量較佳為1,000質量份以下,更佳為700質量份以下之範圍。 The compounding amount of the additive is preferably 1,000 parts by mass or less, and more preferably 700 parts by mass or less based on 100 parts by mass of the curable resin composition.
本實施型態之硬化性樹脂組成物中,可進一步使用環氧樹脂、活性酯化合物、酚樹脂、胺樹脂、順丁烯二醯亞胺化合物、具有乙烯性不飽和鍵的化合物、異氰酸酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、氰酸酯樹脂、聚伸苯基醚化合物、聚丁二烯及其改質物、聚苯乙烯及其改質物等,此等係可使用1種,亦可使用複數種。此等化合物中,就耐熱性、密著性、介電特性之平衡而言,較佳為含有:具有乙烯性不飽和鍵的化合物、氰酸酯樹脂、聚伸苯基醚化合物、聚丁二烯及其改質物、聚苯乙烯及其改質物。藉由含有此等化合物,可改善硬化物之脆性及提升對金屬的密著性,在回流焊時或冷熱循環等可靠性試驗中可抑制封裝的破裂。 In the curable resin composition of this embodiment, epoxy resins, active ester compounds, phenol resins, amine resins, maleimide compounds, compounds having ethylenically unsaturated bonds, isocyanate resins, and Polyamide resin, polyimide resin, cyanate ester resin, polyphenylene ether compound, polybutadiene and its modified products, polystyrene and its modified products, etc., one of these can be used, or Plural types can be used. Among these compounds, in terms of the balance between heat resistance, adhesion and dielectric properties, compounds containing ethylenically unsaturated bonds, cyanate ester resins, polyphenylene ether compounds, polybutylene ether compounds are preferred. Alkene and its modifications, polystyrene and its modifications. By containing these compounds, the brittleness of the hardened material can be improved and the adhesion to the metal can be improved, thereby inhibiting package cracking during reflow soldering or during reliability tests such as hot and cold cycles.
在未另有規定之下,相對於前述式(1)所示之化合物,上述化合物之使用量較佳為10質量倍以下,更佳為5質量倍以下,特佳為3質量倍以下之質量範圍。此外,較佳下限值為0.1質量倍以上,更佳為0.25質量倍以上,又更佳為0.5質量倍以上。藉由設為上述範圍內,可發揮前述式(1)所示之化合物的耐熱性和介電特性之效果,並追加所添加的各化合物的效果。針對此等成分,可使用以下所例示者。 Unless otherwise specified, the usage amount of the above compound is preferably 10 mass times or less, more preferably 5 mass times or less, and particularly preferably 3 mass times or less relative to the compound represented by formula (1). Scope. In addition, a preferable lower limit value is 0.1 mass times or more, more preferably 0.25 mass times or more, and still more preferably 0.5 mass times or more. By setting it within the above range, the effects of the heat resistance and dielectric properties of the compound represented by the aforementioned formula (1) can be exerted, and the effects of each added compound can be added. For these components, those exemplified below can be used.
〔環氧樹脂〕 〔Epoxy resin〕
就環氧樹脂而言,以下雖例示較佳者,惟並非限於此等者。又,環氧樹脂之性狀可為液狀或固形,可使用1種或併用複數種。 As for the epoxy resin, although the following examples are preferred, the examples are not limited to these. Moreover, the nature of the epoxy resin may be liquid or solid, and one type may be used or a plurality of types may be used in combination.
關於液狀環氧樹脂,可列舉例如:雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚AF型環氧樹脂、萘型環氧樹脂、縮水甘油基酯型環氧樹脂、縮水甘油基胺型環氧樹脂、酚酚醛(phenol novolac)型環氧樹脂、具有酯骨架之脂環式環氧樹脂、環己烷型環氧樹脂、環己烷二甲醇型環氧樹脂、縮水甘油基胺型環氧樹脂、及具有丁二烯結構之環氧樹脂等。具體例可列舉如:「RE310S」、「RE410S」(以上為日本化藥公司製之雙酚A型環氧樹脂)、「RE303S」、「RE304S」、「RE403S」、「RE404S」(以上為日本化藥公司製之雙酚F型環氧樹脂)、「HP4032」、「HP4032D」、「HP4032SS」(以上為DIC公司製之萘型環氧樹脂)、「828US」、「jER828EL」、「825」、「828EL」(以上為三菱化學公司製之雙酚A型環氧樹脂)、「jE807」、「1750」(以上為三菱化學公司製之雙酚F型環氧樹脂)、「jER152」(三菱化學公司製之酚酚醛型環氧樹脂)、「630」、「630LSD」(以上為三菱化學公司製之縮水甘油基胺型環氧樹脂)、「ZX1059」(新日鐵住金化學公司製之雙酚A型環氧樹脂與雙酚F型環氧樹脂之混合品)、「EX-721」(Nagase ChemteX公司製之縮水甘油基酯型環氧樹脂)、「CELLOXIDE 2021P」(DAICEL公司製之具有酯骨架之脂環式環氧樹脂)、「PB-3600」(DAICEL公司製之具有丁二烯結構之環氧樹脂)、「ZX1658」、「ZX1658GS」(以上為新日鐵住金化學公司製之液狀1,4-縮水甘油基環己烷型環氧樹脂)等。此等係可單獨使用1種,亦可組合使用2種以上。 Examples of the liquid epoxy resin include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, naphthalene type epoxy resin, glycidyl ester type epoxy resin, Glycidylamine type epoxy resin, phenol novolac type epoxy resin, alicyclic epoxy resin with ester skeleton, cyclohexane type epoxy resin, cyclohexanedimethanol type epoxy resin, shrinkage Glyceryl amine type epoxy resin, and epoxy resin with butadiene structure, etc. Specific examples include: "RE310S", "RE410S" (the above are bisphenol A-type epoxy resins manufactured by Nippon Kayaku Co., Ltd.), "RE303S", "RE304S", "RE403S", "RE404S" (the above are bisphenol A-type epoxy resins manufactured by Nippon Kayaku Co., Ltd.) Bisphenol F-type epoxy resin manufactured by Chemical Company), "HP4032", "HP4032D", "HP4032SS" (the above are naphthalene-type epoxy resin manufactured by DIC Company), "828US", "jER828EL", "825" , "828EL" (the above is a bisphenol A-type epoxy resin manufactured by Mitsubishi Chemical Corporation), "jE807", "1750" (the above is a bisphenol F-type epoxy resin manufactured by Mitsubishi Chemical Corporation), "jER152" (Mitsubishi Chemical Corporation Phenol novolac type epoxy resin manufactured by Chemical Company), "630", "630LSD" (the above is glycidylamine type epoxy resin manufactured by Mitsubishi Chemical Company), "ZX1059" (double epoxy resin manufactured by Nippon Steel & Sumitomo Metal Chemical Company) A mixture of phenol A type epoxy resin and bisphenol F type epoxy resin), "EX-721" (glycidyl ester type epoxy resin manufactured by Nagase ChemteX Co., Ltd.), "CELLOXIDE 2021P" (manufactured by DAICEL Co., Ltd. Alicyclic epoxy resin with ester skeleton), "PB-3600" (epoxy resin with butadiene structure manufactured by DAICEL), "ZX1658", "ZX1658GS" (the above are manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd. Liquid 1,4-glycidylcyclohexane type epoxy resin), etc. One type of these may be used alone, or two or more types may be used in combination.
就固形環氧樹脂而言,較佳為聯二甲酚型環氧樹脂、萘型環氧樹脂、萘型4官能環氧樹脂、甲酚酚醛型環氧樹脂、雙環戊二烯型環氧樹脂、參酚 型環氧樹脂、萘酚型環氧樹脂、聯苯型環氧樹脂、伸萘基醚型環氧樹脂、蔥型環氧樹脂、雙酚A型環氧樹脂、雙酚AF型環氧樹脂、四苯基乙烷型環氧樹脂,可列舉如萘酚型環氧樹脂、雙酚AF型環氧樹脂、萘型環氧樹脂及聯苯型環氧樹脂。具體例可列舉如:「HP4032H」(DIC公司製之萘型環氧樹脂)、「HP-4700」、「HP-4710」(以上為DIC公司製之萘型4官能環氧樹脂)、「N-690」(DIC公司製之甲酚酚醛型環氧樹脂)、「N-695」(DIC公司製之甲酚酚醛型環氧樹脂)、「HP-7200」(DIC公司製之雙環戊二烯型環氧樹脂)、「HP-7200」、「HP-7200HH」、「HP-7200H」(以上為DIC公司製之雙環戊二烯型環氧樹脂)、「EXA-7311」、「EXA-7311-G3」、「EXA-7311-G4」、「EXA-7311-G4S」、「HP-6000」(以上為DIC公司製之伸萘基醚型環氧樹脂)、「EPPN-502H」(日本化藥公司製之參酚型環氧樹脂)、「NC-7000L」、「NC-7300」(以上為日本化藥公司製之萘酚-甲酚酚醛型環氧樹脂)、「NC-3000H」、「NC-3000」、「NC-3000L」、「NC-3100」(以上為日本化藥公司製之聯苯芳烷基型環氧樹脂)、「XD-1000-2L」、「XD-1000-L」、「XD-1000-H」、「XD-1000-H」(以上為日本化藥公司製之雙環戊二烯型環氧樹脂)、「ESN475V」(新日鐵住金化學公司製之萘酚型環氧樹脂)、「ESN485」(新日鐵住金化學公司製之萘酚酚醛型環氧樹脂)、「YX-4000H」、「YX-4000」、「YL6121」(以上為三菱化學公司製之聯苯型環氧樹脂)、「YX-4000HK」(三菱化學公司製之聯二甲酚型環氧樹脂)、「YX-8800」(三菱化學公司製之蔥型環氧樹脂)、「PG-100」、「CG-500」(大阪瓦斯化學公司製之茀系環氧樹脂)、「YL-7760」(三菱化學公司製之雙酚AF型環氧樹脂)、「YL-7800」(三菱化學公司製之茀型環氧樹脂)「jER1010」(三菱化學公司製之固體狀雙酚A型環氧樹脂)、 「jER1031S」(三菱化學公司製之四苯基乙烷型環氧樹脂)等。此等係可單獨使用1種,亦可組合使用2種以上。 As for the solid epoxy resin, preferred are dixylenol type epoxy resin, naphthalene type epoxy resin, naphthalene type tetrafunctional epoxy resin, cresol novolak type epoxy resin, and dicyclopentadiene type epoxy resin. , ginseng phenol Type epoxy resin, naphthol type epoxy resin, biphenyl type epoxy resin, naphthyl ether type epoxy resin, onion type epoxy resin, bisphenol A type epoxy resin, bisphenol AF type epoxy resin, Examples of the tetraphenylethane-type epoxy resin include naphthol-type epoxy resin, bisphenol AF-type epoxy resin, naphthalene-type epoxy resin, and biphenyl-type epoxy resin. Specific examples include: "HP4032H" (naphthalene-type epoxy resin manufactured by DIC), "HP-4700", "HP-4710" (the above is naphthalene-type tetrafunctional epoxy resin manufactured by DIC), "N -690" (cresol novolac epoxy resin manufactured by DIC), "N-695" (cresol novolac epoxy resin manufactured by DIC), "HP-7200" (dicyclopentadiene manufactured by DIC type epoxy resin), "HP-7200", "HP-7200HH", "HP-7200H" (the above is dicyclopentadiene type epoxy resin manufactured by DIC Corporation), "EXA-7311", "EXA-7311 -G3", "EXA-7311-G4", "EXA-7311-G4S", "HP-6000" (the above are naphthyl ether type epoxy resins manufactured by DIC Corporation), "EPPN-502H" (Japanese (Naphthol-cresol novolak type epoxy resin manufactured by Nippon Chemical Company), "NC-7000L", "NC-7300" (the above are naphthol-cresol novolak type epoxy resin manufactured by Nippon Kayaku Company), "NC-3000H", "NC-3000", "NC-3000L", "NC-3100" (the above are biphenyl aralkyl epoxy resins manufactured by Nippon Kayaku Co., Ltd.), "XD-1000-2L", "XD-1000- L", " Phenolic epoxy resin), "ESN485" (naphthol phenolic epoxy resin manufactured by Nippon Steel & Sumitomo Metal Chemical Co., Ltd.), "YX-4000H", "YX-4000", "YL6121" (the above are manufactured by Mitsubishi Chemical Corporation biphenyl-type epoxy resin), "YX-4000HK" (bixylenol-type epoxy resin manufactured by Mitsubishi Chemical Corporation), "YX-8800" (onion-type epoxy resin manufactured by Mitsubishi Chemical Corporation), "PG -100", "CG-500" (bisphenol AF type epoxy resin produced by Osaka Gas Chemical Co., Ltd.), "YL-7760" (bisphenol AF type epoxy resin produced by Mitsubishi Chemical Co., Ltd.), "YL-7800" (Mitsubishi Chemical Co., Ltd. Bisphenol A type epoxy resin manufactured by Mitsubishi Chemical Corporation) "jER1010" (solid bisphenol A type epoxy resin manufactured by Mitsubishi Chemical Corporation), "jER1031S" (tetraphenylethane type epoxy resin manufactured by Mitsubishi Chemical Corporation), etc. One type of these may be used alone, or two or more types may be used in combination.
〔活性酯化合物〕 [Active ester compound]
就活性酯化合物而言,係意指在結構體中含有至少1個酯鍵且在酯鍵之兩側鍵結有脂肪族鏈、脂肪族環或芳香族環的化合物。活性酯化合物可列舉例如酚酯類、硫酚酯類、N-羥基胺酯類、雜環羥基化合物之酯類等在1分子中具有2個以上之反應活性高之酯基的化合物,並且,其係藉由羧酸化合物、醯氯或硫羧酸化合物中之至少一種化合物與羥基化合物或硫醇化合物中之至少一種化合物進行縮合反應而得。尤其,就耐熱性提升之觀點而言,較佳為由羧酸化合物或醯氯與羥基化合物而得,羥基化合物較佳為酚化合物或萘酚化合物。活性酯化合物可單獨使用1種,亦可組合使用2種以上。 The active ester compound means a compound containing at least one ester bond in the structure and an aliphatic chain, aliphatic ring or aromatic ring bonded to both sides of the ester bond. Examples of active ester compounds include compounds having two or more highly reactive ester groups in one molecule, such as phenol esters, thiophenol esters, N-hydroxylamine esters, and esters of heterocyclic hydroxy compounds, and, It is obtained by condensation reaction of at least one compound among a carboxylic acid compound, a chelate chloride or a sulfur carboxylic acid compound, and at least one compound among a hydroxy compound or a thiol compound. In particular, from the viewpoint of improving heat resistance, it is preferably obtained from a carboxylic acid compound or a chloride and a hydroxy compound, and the hydroxy compound is preferably a phenol compound or a naphthol compound. One type of active ester compound may be used alone, or two or more types may be used in combination.
上述羧酸化合物可列舉例如:苯甲酸、乙酸、丁二酸、順丁烯二酸、伊康酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、焦蜜石酸等。 Examples of the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromelonic acid, and the like.
上述醯氯可列舉例如:乙醯氯、丙烯醯氯、甲基丙烯醯氯、丙二醯氯、丁二醯二氯、二甘胺醯氯、戊二醯二氯、辛二醯二氯、癸二醯二氯、己二醯二氯、十二烷二醯二氯、壬醯氯、2,5-呋喃二羰基二氯、鄰苯二甲醯氯、間苯二甲醯氯、對苯二甲醯氯、均苯三甲醯氯、雙(4-氯羰基苯基)醚、4,4’-二苯基二羰基氯、4,4’-偶氮二苯甲醯二氯等。 Examples of the above-mentioned acid chloride include: acetyl chloride, acrylic acid chloride, methacrylic acid chloride, malonyl acid chloride, succinic acid dichloride, diglylamino acid chloride, glutaryl dichloride, suberyl dichloride, Decanediyl dichloride, hexadiyl dichloride, dodecanediyl dichloride, nonyl dichloride, 2,5-furandicarbonyl dichloride, phthalyl chloride, isophthalyl chloride, p-phenylene Dimethyl chloride, trimesylidene chloride, bis(4-chlorocarbonylphenyl) ether, 4,4'-diphenyldicarbonyl chloride, 4,4'-azodibenzyldichloride, etc.
上述酚化合物及上述萘酚化合物可列舉例如:氫醌、間苯二酚(resorcin)、雙酚A、雙酚F、雙酚S、酸式酚酞(Phenolphthalin)、甲基化雙酚A、甲基化雙酚F、甲基化雙酚S、酚、鄰甲酚、間甲酚、對甲酚、兒茶酚(catechol)、α-萘酚、β-萘酚、1,5-二羥基萘、1,6-二羥基萘、2,6-二羥基萘、二羥基二苯甲酮、 三羥基二苯甲酮、四羥基二苯甲酮、均苯三酚(phloroglucin)、苯三醇、雙環戊二烯型二酚化合物、酚酚醛、後述酚樹脂等。於此,「雙環戊二烯型二酚化合物」係意指藉由使雙環戊二烯1分子與酚2分子進行縮合而得的二酚化合物。 Examples of the above-mentioned phenol compound and the above-mentioned naphthol compound include hydroquinone, resorcin, bisphenol A, bisphenol F, bisphenol S, acid phenolphthalin (Phenolphthalin), methylated bisphenol A, and methane. Sylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxy Naphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, Trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, phloroglucin, dicyclopentadiene-type diphenol compound, phenol novolac, phenol resin described below, etc. Here, the "dicyclopentadiene-type diphenol compound" means a diphenol compound obtained by condensing one molecule of dicyclopentadiene and two molecules of phenol.
活性酯化合物之較佳具體例可列舉:包含雙環戊二烯型二酚結構之活性酯化合物、包含萘結構之活性酯化合物、包含酚酚醛之乙醯化物的活性酯化合物、包含酚酚醛之苯甲醯化物的活性酯化合物、國際公開第2020/095829號公報之實施例2所記載之化合物、國際公開第2020/059625號所揭示的化合物等。其中,更佳為包含萘結構之活性酯化合物、包含雙環戊二烯型二酚結構之活性酯化合物。所謂雙環戊二烯型二酚結構係表示由伸苯基-二環戊烯-伸苯基所構成之2價結構單元。 Preferable specific examples of the active ester compound include: an active ester compound containing a dicyclopentadiene-type diphenol structure, an active ester compound containing a naphthalene structure, an active ester compound containing an acetate of phenolic novolac, and a benzene compound containing a phenolic novolac. Active ester compounds of formate compounds, compounds described in Example 2 of International Publication No. 2020/095829, compounds disclosed in International Publication No. 2020/059625, etc. Among these, active ester compounds containing a naphthalene structure and active ester compounds containing a dicyclopentadiene-type diphenol structure are more preferred. The so-called dicyclopentadiene-type diphenol structure represents a divalent structural unit composed of a phenylene group-dicyclopentene-phenylene group.
關於活性酯化合物之市售品,例如,包含雙環戊二烯型二酚結構之活性酯化合物可列舉「EXB9451」、「EXB9460」、「EXB9460S」、「HPC-8000-65T」、「HPC-8000H-65TM」、「EXB-8000L-65TM」、「EXB-8150-65T」(DIC公司製),包含萘結構之活性酯化合物可列舉「EXB9416-70BK」(DIC公司製),包含酚酚醛之乙醯化物的活性酯化合物可列舉「DC808」(三菱化學公司製),包含酚酚醛之苯甲醯化物的活性酯化合物可列舉「YLH1026」、「YLH1030」、「YLH1048」(三菱化學公司製),屬於「酚酚醛之乙醯化物」的活性酯系硬化劑可列舉「DC808」(三菱化學公司製),包含磷原子之活性酯系硬化劑可列舉DIC公司製之「EXB-9050L-62M」等。 Regarding commercially available active ester compounds, for example, active ester compounds containing a dicyclopentadiene-type diphenol structure include "EXB9451", "EXB9460", "EXB9460S", "HPC-8000-65T", and "HPC-8000H" -65TM", "EXB-8000L-65TM", "EXB-8150-65T" (manufactured by DIC Corporation). Examples of active ester compounds containing a naphthalene structure include "EXB9416-70BK" (manufactured by DIC Corporation), which contains phenolic phenolic aldehydes. Examples of the active ester compound of the acyl compound include "DC808" (manufactured by Mitsubishi Chemical Corporation), and examples of the active ester compound of the benzyl acyl compound containing phenol novolac include "YLH1026", "YLH1030", and "YLH1048" (manufactured by Mitsubishi Chemical Corporation). Examples of active ester-based hardeners that are "acetyl compounds of phenolic novolac" include "DC808" (manufactured by Mitsubishi Chemical Corporation), and examples of active ester-based hardeners containing phosphorus atoms include "EXB-9050L-62M" manufactured by DIC Corporation, etc. .
關於活性酯化合物及環氧樹脂之調配比,活性酯當量(α)與環氧當量(β)之比率(α/β)較佳為0.5至1.5,更佳為0.8至1.2,又更佳為0.90至1.10。在為上述範圍以外之情況下,則有體系中殘留過多之環氧基或活性酯基之虞,在高 溫放置試驗(150℃、1000小時等)或高溫高濕條件下(溫度85℃、濕度85%等)之長期可靠性試驗等有特性劣化之虞。 Regarding the blending ratio of the active ester compound and the epoxy resin, the ratio (α/β) of the active ester equivalent (α) to the epoxy equivalent (β) is preferably 0.5 to 1.5, more preferably 0.8 to 1.2, and still more preferably 0.90 to 1.10. If it is outside the above range, there is a risk that too many epoxy groups or active ester groups will remain in the system. High temperature exposure tests (150°C, 1000 hours, etc.) or long-term reliability tests under high temperature and high humidity conditions (temperature 85°C, humidity 85%, etc.) may lead to deterioration in characteristics.
〔酚樹脂〕 [Phenol resin]
酚樹脂係意指在分子內具有2個以上之酚性羥基的化合物。酚樹脂可列舉例如酚類與醛類之反應物、酚類與二烯化合物之反應物、酚類與酮類之反應物、酚類與經取代之聯苯類之反應物、酚類與經取代之苯基類之反應物、雙酚類與醛類之反應物等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 Phenolic resin means a compound having two or more phenolic hydroxyl groups in the molecule. Examples of the phenolic resin include reactants of phenols and aldehydes, reactants of phenols and diene compounds, reactants of phenols and ketones, reactants of phenols and substituted biphenyls, and reactants of phenols and hydrocarbons. Reactants of substituted phenyls, reactants of bisphenols and aldehydes, etc., but are not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used.
以下例示上述各原料之具體例,惟並非限於此等者。 Specific examples of each of the above-mentioned raw materials are illustrated below, but are not limited to these.
<酚類> <Phenols>
酚、經烷基取代之酚、經芳香族取代之酚、氫醌、間苯二酚、萘酚、經烷基取代之萘酚、二羥基苯、經烷基取代之二羥基苯、二羥基萘等。 Phenol, alkyl-substituted phenol, aromatic-substituted phenol, hydroquinone, resorcinol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxybenzene Naphthalene etc.
<醛類> <Aldehydes>
甲醛、乙醛、烷基醛、苯甲醛、經烷基取代之苯甲醛、羥基苯甲醛、萘醛、戊二醛、鄰苯二甲醛、巴豆醛、肉桂醛、糠醛等。 Formaldehyde, acetaldehyde, alkyl aldehydes, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, o-phthalaldehyde, crotonaldehyde, cinnamic aldehyde, furfural, etc.
<二烯化合物> <diene compound>
雙環戊二烯、萜類、乙烯基環己烯、降莰烷二烯、乙烯基降莰烷烯、四氫茚、二乙烯基苯、二乙烯基聯苯、二異丙烯基聯苯、丁二烯、異戊二烯等。 Dicyclopentadiene, terpenes, vinylcyclohexene, norbornanediene, vinylnorbornane, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butyl Diene, isoprene, etc.
<酮類> <Ketones>
丙酮、甲基乙基酮、甲基異丁基酮、苯乙酮、二苯甲酮、茀酮等。 Acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, quinone, etc.
<經取代之聯苯類> <Substituted biphenyls>
4,4’-雙(氯甲基)-1,1’-聯苯、4,4’-雙(甲氧基甲基)-1,1’-聯苯、4,4’-雙(羥基甲基)-1,1’-聯苯等。 4,4'-bis(chloromethyl)-1,1'-biphenyl, 4,4'-bis(methoxymethyl)-1,1'-biphenyl, 4,4'-bis(hydroxy Methyl)-1,1'-biphenyl, etc.
<經取代之苯基類> <Substituted phenyls>
1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯、1,4-雙(羥基甲基)苯等。 1,4-bis(chloromethyl)benzene, 1,4-bis(methoxymethyl)benzene, 1,4-bis(hydroxymethyl)benzene, etc.
〔胺樹脂〕 [Amine resin]
胺樹脂係意指在分子內具有2個以上之胺基的化合物。胺樹脂可列舉例如二胺基二苯基甲烷、二胺基二苯基碸、異佛酮二胺、萘二胺、苯胺酚醛(苯胺與福馬林之反應物)、N-甲基苯胺酚醛(N-甲基苯胺與福馬林之反應物)、鄰乙基苯胺酚醛(鄰乙基苯胺與福馬林之反應物)、2-甲基苯胺與福馬林之反應物、2,6-二異丙基苯胺與福馬林之反應物、2,6-二乙基苯胺與福馬林之反應物、2-乙基-6-乙基苯胺與福馬林之反應物、2,6-二甲基苯胺與福馬林之反應物、由苯胺與二甲苯氯之反應而得的苯胺樹脂、日本專利第6429862號公報所記載的苯胺與經取代之聯苯類(例如4,4’-雙(氯甲基)-1,1’-聯苯及4,4’-雙(甲氧基甲基)-1,1’-聯苯等)之反應物、苯胺與經取代之苯基類(1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯及1,4-雙(羥基甲基)苯等)之反應物、4,4’-(1,3-伸苯基二亞異丙基)雙苯胺、4,4’-(1,4-伸苯基二亞異丙基)雙苯胺、苯胺與二異丙烯基苯之反應物、二聚二胺等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 Amine resin means a compound having two or more amine groups in the molecule. Examples of the amine resin include diaminodiphenylmethane, diaminodiphenylmethane, isophoronediamine, naphthalenediamine, aniline phenolic (the reaction product of aniline and formalin), N-methylaniline phenolic ( The reactant of N-methylaniline and formalin), o-ethylaniline phenolic (the reactant of o-ethylaniline and formalin), the reactant of 2-methylaniline and formalin, 2,6-diisopropyl The reactant of 2,6-diethylaniline and formalin, the reactant of 2,6-diethylaniline and formalin, the reactant of 2-ethyl-6-ethylaniline and formalin, the reactant of 2,6-dimethylaniline and formalin Reactants of formalin, aniline resin obtained from the reaction of aniline and xylene chloride, aniline and substituted biphenyls (such as 4,4'-bis(chloromethyl)) described in Japanese Patent No. 6429862 - Reactants of 1,1'-biphenyl and 4,4'-bis(methoxymethyl)-1,1'-biphenyl, etc.), aniline and substituted phenyls (1,4-bis (Chloromethyl)benzene, 1,4-bis(methoxymethyl)benzene and 1,4-bis(hydroxymethyl)benzene, etc.), 4,4'-(1,3-phenylene) Diisopropylidene)bisaniline, 4,4'-(1,4-phenylenediisopropylene)bisaniline, reactants of aniline and diisopropenylbenzene, dimerdiamine, etc., only It is not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used.
〔式(1)所示之順丁烯二醯亞胺化合物以外之順丁烯二醯亞胺化合物〕 [Maleimine compounds other than maleimide compounds represented by formula (1)]
順丁烯二醯亞胺化合物係意指在分子內具有1個以上之順丁烯二醯亞胺基的化合物。本實施型態之硬化性樹脂組成物可更含有式(1)所示之順丁烯二醯亞胺化合物以外之順丁烯二醯亞胺化合物。關於式(1)所示之順丁烯二醯亞胺化合 物以外之順丁烯二醯亞胺化合物,可列舉例如4,4’-二苯基甲烷雙順丁烯二醯亞胺、聚苯基甲烷順丁烯二醯亞胺、間伸苯基雙順丁烯二醯亞胺、2,2’-雙[4-(4-順丁烯二醯亞胺苯氧基)苯基]丙烷、3,3’-二甲基-5,5’-二乙基-4,4’-二苯基甲烷雙順丁烯二醯亞胺、4-甲基-1,3-伸苯基雙順丁烯二醯亞胺、4,4’-二苯基醚雙順丁烯二醯亞胺、4,4’-二苯基碸雙順丁烯二醯亞胺、1,3-雙(3-順丁烯二醯亞胺苯氧基)苯、1,3-雙(4-順丁烯二醯亞胺苯氧基)苯)、Xyloc型順丁烯二醯亞胺化合物(ANILIX順丁烯二醯亞胺,三井化學FINE公司製)、聯苯芳烷基型順丁烯二醯亞胺化合物(日本特開2009-001783號公報之實施例4記載之藉由將包含順丁烯二醯亞胺化合物(M2)的樹脂溶液在減壓下溶劑餾去而固形化者)、雙胺基異丙苯基苯型順丁烯二醯亞胺(國際公開第2020/054601號記載之順丁烯二醯亞胺化合物)、日本專利-6629692號或國際公開第2020/217679號記載之具有茚烷結構的順丁烯二醯亞胺化合物、MATERIAL STAGE,Vol.18,No.12,2019『~續‧環氧樹脂CAS編號物語~硬化劑CAS編號備忘錄第31回雙順丁烯二醯亞胺(1)』、和MATERIAL STAGE,Vol.19,No.2,2019『~續‧環氧樹脂CAS編號物語~硬化劑CAS編號備忘錄 第32回 雙順丁烯二醯亞胺(2)』所公開的順丁烯二醯亞胺化合物等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 The maleimide compound means a compound having one or more maleimide groups in the molecule. The curable resin composition of this embodiment may further contain a maleimide compound other than the maleimide compound represented by formula (1). About the maleic imine compound represented by formula (1) Examples of maleimide compounds other than those of Maleimide, 2,2'-bis[4-(4-maleimidephenoxy)phenyl]propane, 3,3'-dimethyl-5,5'- Diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 4,4'-diphenyl Ether bis-maleyl imide, 4,4'-diphenyl bis-maleyl imide, 1,3-bis(3-maleyl imide phenoxy)benzene, 1,3-Bis(4-maleimidephenoxy)benzene), Xyloc-type maleimide compound (ANILIX maleimide, manufactured by Mitsui Chemicals FINE Co., Ltd.), Phenyl aralkyl type maleimide compound (described in Example 4 of Japanese Patent Application Laid-Open No. 2009-001783), by placing a resin solution containing a maleimide compound (M2) under reduced pressure. The solvent is distilled off and solidified), bisaminocumylbenzene-type maleimide (maleimide compound described in International Publication No. 2020/054601), Japanese Patent No. 6629692 Or the maleimide compound with an indene structure described in International Publication No. 2020/217679, MATERIAL STAGE, Vol. 18, No. 12, 2019『~Continued‧Epoxy Resin CAS Number Story~Hardening Agent CAS Numbering Memorandum Chapter 31 Bismaleimide (1)", and MATERIAL STAGE, Vol.19, No.2, 2019 "~Continued‧ Epoxy Resin CAS Numbering Story ~ Hardener CAS Numbering Memorandum Chapter 32 However, it is not limited to the maleimide compounds disclosed in "Bismaleimide (2)" and the like. In addition, one type of these systems may be used, or a plurality of types may be used.
相對於前述式(1)所示之順丁烯二醯亞胺化合物,式(1)所示之順丁烯二醯亞胺化合物以外之順丁烯二醯亞胺化合物的添加量較佳為10質量倍以下,更佳為5質量倍以下,特佳為3質量倍以下之質量範圍。此外,較佳下限值為0.01質量倍以上,更佳為0.1質量倍以上。若為上述範圍,則可發揮前述式(1)所示之化合物之耐熱性、介電特性、低吸水性之效果。 The amount of the maleimide compound other than the maleimide compound represented by the formula (1) is preferably added to the maleimide compound represented by the formula (1). 10 mass times or less, more preferably 5 mass times or less, particularly preferably 3 mass times or less. In addition, a preferable lower limit value is 0.01 mass times or more, and more preferably 0.1 mass times or more. If it is within the above range, the effects of heat resistance, dielectric properties, and low water absorption properties of the compound represented by the aforementioned formula (1) can be exerted.
〔具有乙烯性不飽和鍵之化合物〕 [Compounds with ethylenically unsaturated bonds]
具有乙烯性不飽和鍵之化合物係意指,無論使用或不使用聚合起始劑,在分子內具有1個以上之可藉由熱或光而聚合之乙烯性不飽和鍵的化合物。 The compound having an ethylenically unsaturated bond means a compound having one or more ethylenically unsaturated bonds polymerizable by heat or light in the molecule regardless of whether a polymerization initiator is used or not.
關於具有乙烯性不飽和鍵的化合物,可列舉例如:前述酚樹脂與具有乙烯性不飽和鍵之鹵素系化合物(氯甲基苯乙烯、烯丙基氯、甲基烯丙基氯、丙烯醯氯、甲基丙烯醯氯等)的反應物、具有乙烯性不飽和鍵之酚類(2-烯丙基酚、2-丙烯基酚、4-烯丙基酚、4-丙烯基酚、丁香酚、異丁香酚等)與鹵素系化合物(1,4-雙(氯甲基)苯、4,4’-雙(氯甲基)聯苯、4,4’-二氟二苯甲酮、4,4’-二氯二苯甲酮、4,4’-二溴二苯甲酮、三聚氯化氰等)的反應物、環氧樹脂或醇類與(甲基)丙烯酸類(丙烯酸、甲基丙烯酸等)之反應物、及此等之酸改質化物等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 Examples of the compound having an ethylenically unsaturated bond include the aforementioned phenol resin and a halogen compound having an ethylenically unsaturated bond (chloromethylstyrene, allyl chloride, methallyl chloride, acryl chloride , methacrylic acid chloride, etc.), phenols with ethylenically unsaturated bonds (2-allylphenol, 2-propenylphenol, 4-allylphenol, 4-propenylphenol, eugenol , isoeugenol, etc.) and halogen compounds (1,4-bis(chloromethyl)benzene, 4,4'-bis(chloromethyl)biphenyl, 4,4'-difluorobenzophenone, 4 , 4'-dichlorobenzophenone, 4,4'-dibromobenzophenone, cyanogen chloride, etc.), epoxy resin or alcohol and (meth)acrylic acid (acrylic acid, Methacrylic acid, etc.), and acid modified products thereof, but are not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used.
〔異氰酸酯樹脂〕 [Isocyanate resin]
異氰酸酯樹脂係意指在分子內具有2個以上之異氰酸酯基的化合物。異氰酸酯樹脂可列舉例如:對伸苯基二異氰酸酯、間伸苯基二異氰酸酯、對二甲苯二異氰酸酯、間二甲苯二異氰酸酯、2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、4,4’-二苯基甲烷二異氰酸酯、萘二異氰酸酯等芳香族二異氰酸酯類、異佛酮二異氰酸酯、六亞甲基二異氰酸酯、4,4’-二環己基甲烷二異氰酸酯、氫化二甲苯二異氰酸酯、降莰烯二異氰酸酯、離胺酸二異氰酸酯等脂肪族或脂環結構之二異氰酸酯類、異氰酸酯單體之一種以上的縮二脲((biuret)體、或將上述二異氰酸酯化合物進行三聚化而成的異氰酸酯體等聚異氰酸酯、藉由上述異氰酸酯化合物與多元醇化合物之胺甲酸乙酯化反應而得的聚異氰酸酯等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 Isocyanate resin means a compound having two or more isocyanate groups in the molecule. Examples of the isocyanate resin include p-phenylene diisocyanate, m-phenylene diisocyanate, p-xylene diisocyanate, m-xylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4, Aromatic diisocyanates such as 4'-diphenylmethane diisocyanate, naphthalene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, hydrogenated xylene diisocyanate , aliphatic or alicyclic diisocyanates such as norbornene diisocyanate and lysine diisocyanate, biurets of one or more isocyanate monomers, or trimerization of the above diisocyanate compounds Polyisocyanates such as polyisocyanates obtained by the isocyanate compound and polyisocyanates obtained by the urethanation reaction of the above-mentioned isocyanate compounds and polyol compounds are not limited to these. In addition, one type of these may be used. Plural types can be used.
〔聚醯胺樹脂〕 [Polyamide resin]
聚醯胺樹脂可列舉例如:二胺、二異氰酸酯、唑啉中之任1種以上與二羧酸之反應物、二胺與醯氯之反應物、內醯胺化合物之開環聚合物。此外,此等係可使用1種,亦可使用複數種。 Examples of polyamide resin include: diamine, diisocyanate, Reactants of any one or more oxazolines with dicarboxylic acids, reactants of diamines and chloride, and ring-opening polymers of lactam compounds. In addition, one type of these systems may be used, or a plurality of types may be used.
以下例示上述各原料之具體例,惟並非限於此等者。 Specific examples of each of the above-mentioned raw materials are illustrated below, but are not limited to these.
<二胺> <Diamine>
乙二胺、三亞甲基二胺、四亞甲基二胺、五亞甲基二胺、六亞甲基二胺、七亞甲基二胺、八亞甲基二胺、九亞甲基二胺、癸二胺、十一烷二胺、十二烷二胺、十三烷二胺、十四烷二胺、十五烷二胺、十六烷二胺、十七烷二胺、十八烷二胺、十九烷二胺、二十烷二胺、2-甲基-1,5-二胺基戊烷、2-甲基-1,8-二胺基辛烷、二聚二胺、環己烷二胺、雙-(4-胺基環己基)甲烷、雙(3-甲基-4-胺基環己基)甲烷、二甲苯二胺、降莰烯二胺、異佛酮二胺、雙胺基甲基三環癸烷、伸苯基二胺、二乙基甲苯二胺、萘二胺、二胺基二苯基甲烷、雙(4-胺基-3,5-二甲基苯基)甲烷雙(4-胺基-3,5-二乙基苯基)甲烷、4,4'-亞甲基雙-鄰甲基苯胺、4,4'-亞甲基雙-鄰乙基苯胺、4,4'-亞甲基雙-2-乙基-6-甲基苯胺、4,4'-亞甲基雙-2,6-二異丙基苯胺、4,4-伸乙基二苯胺、二胺基二苯基碸、二胺基二苯基醚、1,3-雙(3-胺基苯氧基)苯、1,3-雙(4-胺基苯氧基)苯、4,4-雙(4-胺基苯氧基)聯苯、2,2-雙[4-(4-胺基苯氧基)苯基]丙烷、雙[4-(4-胺基苯氧基)苯基]碸、2,2-雙(3-胺基-4-羥基苯基)丙烷、2,2-雙(4-胺基苯基)六氟丙烷、4,4'-(1,3-伸苯基二亞異丙基)雙苯胺、4,4'-(1,4-伸苯基二亞異丙基)雙苯胺、9,9-雙(4-胺基苯基)茀、2,7-二胺基茀、胺基苄基胺、二胺基二苯甲酮等。 Ethylenediamine, trimethylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine Amine, decanediamine, undecanediamine, dodecanediamine, tridecanediamine, tetradecanediamine, pentadecanediamine, hexadecanediamine, heptadecanediamine, octadecanediamine Alkanediamine, nonadecanediamine, eicosanediamine, 2-methyl-1,5-diaminopentane, 2-methyl-1,8-diaminooctane, dimerdiamine , cyclohexanediamine, bis-(4-aminocyclohexyl)methane, bis(3-methyl-4-aminocyclohexyl)methane, xylenediamine, norbornenediamine, isophoronediamine Amine, bisaminomethyltricyclodecane, phenylenediamine, diethyltoluenediamine, naphthalenediamine, diaminodiphenylmethane, bis(4-amino-3,5-dimethyl methylphenyl)methanebis(4-amino-3,5-diethylphenyl)methane, 4,4'-methylenebis-o-methylaniline, 4,4'-methylenebis-o-methylaniline Ethylaniline, 4,4'-methylenebis-2-ethyl-6-methylaniline, 4,4'-methylenebis-2,6-diisopropylaniline, 4,4-ethylaniline Ethyldiphenylamine, diaminodiphenyl sulfide, diaminodiphenyl ether, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy) )benzene, 4,4-bis(4-aminophenoxy)biphenyl, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, bis[4-(4-amine hydroxyphenoxy)phenyl]propane, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 2,2-bis(4-aminophenyl)hexafluoropropane, 4,4' -(1,3-phenylenediisopropylidene)bisaniline, 4,4'-(1,4-phenylenediisopropylene)bisaniline, 9,9-bis(4-amino) Phenyl) fluorine, 2,7-diamino fluorine, amino benzyl amine, diamino benzophenone, etc.
<二異氰酸酯> <Diisocyanate>
苯二異氰酸酯、甲苯二異氰酸酯、1,3-雙(異氰酸基甲基)苯、1,3-雙(異氰酸基甲基)環己烷、雙(4-異氰酸基苯基)甲烷、異佛酮二異氰酸酯、1,3-雙(2-異氰酸基-2-丙基)苯、2,2-雙(4-異氰酸基苯基)六氟丙烷、二環己基甲烷-4,4'-二異氰酸酯等。 Phylene diisocyanate, toluene diisocyanate, 1,3-bis(isocyanatomethyl)benzene, 1,3-bis(isocyanatomethyl)cyclohexane, bis(4-isocyanatophenyl) )methane, isophorone diisocyanate, 1,3-bis(2-isocyanato-2-propyl)benzene, 2,2-bis(4-isocyanatophenyl)hexafluoropropane, bicyclo Hexylmethane-4,4'-diisocyanate, etc.
<二羧酸> <Dicarboxylic acid>
草酸、丙二酸、丁二酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、十一烷二酸、十二烷二酸、對苯二甲酸、間苯二甲酸、5-羥基間苯二甲酸、2-氯對苯二甲酸、2-甲基對苯二甲酸、5-甲基間苯二甲酸、5-間苯二甲酸磺酸鈉、六氫對苯二甲酸、六氫間苯二甲酸、環己烷二甲酸、聯苯二甲酸、萘二甲酸、二苯甲酮二甲酸、呋喃二甲酸、4,4'-二羧基二苯基醚、4,4'-二羧基二苯基硫醚等。 Oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, terephthalic acid, isophthalic acid Formic acid, 5-hydroxyisophthalic acid, 2-chloroterephthalic acid, 2-methylterephthalic acid, 5-methylisophthalic acid, sodium 5-isophthalic acid sulfonate, hexahydrocerephthalic acid Dicarboxylic acid, hexahydroisophthalic acid, cyclohexanedicarboxylic acid, biphenyldicarboxylic acid, naphthalenedicarboxylic acid, benzophenonedicarboxylic acid, furandicarboxylic acid, 4,4'-dicarboxyldiphenyl ether, 4, 4'-Dicarboxydiphenyl sulfide, etc.
<醯氯> <Chloride>
乙醯氯、丙烯醯氯、甲基丙烯醯氯、丙二醯氯、丁二醯二氯、二甘胺醯氯、戊二醯二氯、辛二醯二氯、癸二醯二氯、己二醯二氯、十二烷二醯氯、壬醯氯、2,5-呋喃二羰基二氯、鄰苯二甲醯氯、間苯二甲醯氯、對苯二甲醯氯、均苯三甲醯氯、雙(4-氯羰基苯基)醚、4,4’-二苯基二羰基氯、4,4’-偶氮二苯甲醯二氯等。 Acetyl chloride, acrylic acid chloride, methacrylic acid chloride, malonyl chloride, succinic acid dichloride, digylamine chloride, glutadiyl dichloride, octadienyl dichloride, hexanediyl dichloride Dichloride, dodecanediyl chloride, nonyl chloride, 2,5-furandicarbonyl dichloride, phthalyl chloride, isophthalyl chloride, terephthalyl chloride, trimethyl Cyl chloride, bis(4-chlorocarbonylphenyl) ether, 4,4'-diphenyldicarbonyl chloride, 4,4'-azodibenzyl chloride, etc.
<內醯胺> <Lactamide>
ε-己內醯胺、ω-十一烷內醯胺、ω-月桂內醯胺等。 ε-caprolactam, ω-undecylactam, ω-laurolactam, etc.
〔聚醯亞胺樹脂〕 [Polyimide resin]
聚醯亞胺樹脂可列舉例如前述二胺與以下所例示的四羧酸二酐之反應物,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 Examples of the polyimide resin include, but are not limited to, reactants of the aforementioned diamines and the tetracarboxylic dianhydride exemplified below. In addition, one type of these systems may be used, or a plurality of types may be used.
<四羧酸二酐> <Tetracarboxylic dianhydride>
4,4’-(六氟亞異丙基)二鄰苯二甲酸酐、5-(2,5-二側氧基四氫-3-呋喃基)-3-甲基-環己烯-1,2-二甲酸酐、焦蜜石酸二酐、1,2,3,4-苯四甲酸二酐、3,3’,4,4’-二苯甲 酮四甲酸二酐、2,2’,3,3’-二苯甲酮四甲酸二酐、3,3’,4,4’-聯苯四甲酸二酐、3,3’,4,4’-二苯基碸四甲酸二酐、2,2’,3,3’-聯苯四甲酸二酐、亞甲基-4,4’-二鄰苯二甲酸二酐、1,1-亞乙基-4,4’-二鄰苯二甲酸二酐、2,2’-亞丙基-4,4’-二鄰苯二甲酸二酐、1,2-伸乙基-4,4’-二鄰苯二甲酸二酐、1,3-三亞甲基-4,4’-二鄰苯二甲酸二酐、1,4-四亞甲基-4,4’-二鄰苯二甲酸二酐、1,5-五亞甲基-4,4’-二鄰苯二甲酸二酐、4,4’-氧基二鄰苯二甲酸二酐、硫基-4,4’-二鄰苯二甲酸二酐、磺醯基-4,4’-二鄰苯二甲酸二酐、1,3-雙(3,4-二羧基苯基)苯二酐、1,3-雙(3,4-二羧基苯氧基)苯二酐、1,4-雙(3,4-二羧基苯氧基)苯二酐、1,3-雙[2-(3,4-二羧基苯基)-2-丙基]苯二酐、1,4-雙[2-(3,4-二羧基苯基)-2-丙基]苯二酐、雙[3-(3,4-二羧基苯氧基)苯基]甲烷二酐、雙[4-(3,4-二羧基苯氧基)苯基]甲烷二酐、2,2-雙[3-(3,4-二羧基苯氧基)苯基]丙烷二酐、2,2-雙[4-(3,4-二羧基苯氧基)苯基]丙烷二酐、雙(3,4-二羧基苯氧基)二甲基矽烷二酐、1,3-雙(3,4-二羧基苯基)-1,1,3,3-四甲基二矽氧烷二酐、2,3,6,7-萘四甲酸二酐、1,4,5,8-萘四甲酸二酐、1,2,5,6-萘四甲酸二酐、3,4,9,10-苝在四甲酸二酐、2,3,6,7-蔥四甲酸二酐、1,2,7,8-菲四甲酸二酐、乙烯四甲酸二酐、1,2,3,4-丁烷四甲酸二酐、1,2,3,4-環丁烷四甲酸二酐)、環戊烷四甲酸二酐、環己烷-1,2,3,4-四甲酸二酐、環己烷-1,2,4,5-四甲酸二酐、3,3’,4,4’-雙環己基四甲酸二酐、羰基-4,4’-雙(環己烷-1,2-二甲酸)二酐、亞甲基-4,4’-雙(環己烷-1,2-二甲酸)二酐、1,2-伸乙基-4,4’-雙(環己烷-1,2-二甲酸)二酐、1,1-亞乙基-4,4’-雙(環己烷-1,2-二甲酸)二酐、2,2-亞丙基-4,4’-雙(環己烷-1,2-二甲酸)二酐、氧基-4,4’-雙(環己烷-1,2-二甲酸)二酐、硫基-4,4’-雙(環己烷-1,2-二甲酸)二酐、磺醯基-4,4’-雙(環己烷-1,2-二甲酸)二酐、雙環[2,2,2]辛-7-烯-2,3,5,6-四甲酸二酐、rel-[1S,5R,6R]-3-氧雜雙環[3,2,1]辛-2,4-二酮-6-螺-3’-(四氫呋喃-2’,5’-二酮)、4-(2,5-二側氧基四氫呋喃-3-基)-1,2,3,4- 四氫萘-1,2-二甲酸酐、乙二醇-雙-(3,4-二甲酸酐苯基)醚、4,4’-聯苯雙(偏苯三酸單酯酸酐)、9,9’-雙(3,4-二羧基苯基)茀二酐等。 4,4'-(Hexafluoroisopropylidene)diphthalic anhydride, 5-(2,5-dilateral oxytetrahydro-3-furyl)-3-methyl-cyclohexene-1 ,2-dicarboxylic anhydride, pyromelite dianhydride, 1,2,3,4-pyromellitic dianhydride, 3,3',4,4'-diphenylmethyl Ketotetracarboxylic dianhydride, 2,2',3,3'-benzophenone tetracarboxylic dianhydride, 3,3',4,4'-biphenyl tetracarboxylic dianhydride, 3,3',4,4 '-Diphenyltetracarboxylic dianhydride, 2,2',3,3'-biphenyltetracarboxylic dianhydride, methylene-4,4'-diphthalic dianhydride, 1,1-phenylenetetracarboxylic dianhydride Ethyl-4,4'-diphthalic dianhydride, 2,2'-propylene-4,4'-diphthalic dianhydride, 1,2-ethyl-4,4' -Diphthalic dianhydride, 1,3-trimethylene-4,4'-diphthalic dianhydride, 1,4-tetramethylene-4,4'-diphthalic acid dianhydride Anhydride, 1,5-pentamethylene-4,4'-diphthalic dianhydride, 4,4'-oxydiphthalic dianhydride, thio-4,4'-diphthalic acid Dicarboxylic dianhydride, sulfonyl-4,4'-diphthalic dianhydride, 1,3-bis(3,4-dicarboxyphenyl)phthalic anhydride, 1,3-bis(3,4 -Dicarboxyphenoxy)phthalic anhydride, 1,4-bis(3,4-dicarboxyphenoxy)phthalic anhydride, 1,3-bis[2-(3,4-dicarboxyphenyl)- 2-propyl]phthalic anhydride, 1,4-bis[2-(3,4-dicarboxyphenyl)-2-propyl]phthalic anhydride, bis[3-(3,4-dicarboxyphenoxy) methyl)phenyl]methane dianhydride, bis[4-(3,4-dicarboxyphenoxy)phenyl]methane dianhydride, 2,2-bis[3-(3,4-dicarboxyphenoxy) Phenyl]propane dianhydride, 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride, bis(3,4-dicarboxyphenoxy)dimethylsilane dianhydride Anhydride, 1,3-bis(3,4-dicarboxyphenyl)-1,1,3,3-tetramethyldisiloxane dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, 1,2,5,6-naphthalene tetracarboxylic dianhydride, 3,4,9,10-perylene tetracarboxylic dianhydride, 2,3,6,7 -Onion tetracarboxylic dianhydride, 1,2,7,8-phenanthrene tetracarboxylic dianhydride, ethylene tetracarboxylic dianhydride, 1,2,3,4-butane tetracarboxylic dianhydride, 1,2,3,4- cyclobutane tetracarboxylic dianhydride), cyclopentane tetracarboxylic dianhydride, cyclohexane-1,2,3,4-tetracarboxylic dianhydride, cyclohexane-1,2,4,5-tetracarboxylic dianhydride , 3,3',4,4'-biscyclohexyltetracarboxylic dianhydride, carbonyl-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, methylene-4,4'- Bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, 1,2-ethylidene-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, 1,1-ethylidene dianhydride Ethyl-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, 2,2-propylene-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, oxy-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, thio-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride , Sulfonyl-4,4'-bis(cyclohexane-1,2-dicarboxylic acid) dianhydride, bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic acid Dianhydride, rel-[1S,5R,6R]-3-oxabicyclo[3,2,1]octan-2,4-dione-6-spiro-3'-(tetrahydrofuran-2',5'- dione), 4-(2,5-bisoxytetrahydrofuran-3-yl)-1,2,3,4- Tetralin-1,2-dicarboxylic anhydride, ethylene glycol-bis-(3,4-dicarboxylic anhydride phenyl) ether, 4,4'-biphenyl bis(trimellitic acid monoester anhydride), 9 , 9'-Bis(3,4-dicarboxyphenyl) dianhydride, etc.
〔氰酸酯樹脂〕 [Cyanate ester resin]
氰酸酯樹脂係使酚樹脂與鹵化氰進行反應而得的氰酸酯化合物,具體例可列舉二氰酸基苯、三氰酸基苯、二氰酸基萘、二氰酸基聯苯、2,2’-雙(4-氰酸基苯基)丙烷、雙(4-氰酸基苯基)甲烷、雙(3,5-二甲基-4-氰酸基苯基)甲烷、2,2’-雙(3,5-二甲基-4-氰酸基苯基)丙烷、2,2’-雙(4-氰酸基苯基)乙烷、2,2’-雙(4-氰酸基苯基)六氟丙烷、雙(4-氰酸基苯基)碸、雙(4-氰酸基苯基)硫基醚、酚酚醛氰酸酯、將酚-雙環戊二烯共縮合物之羥基轉化為氰酸酯基而成者等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。 The cyanate ester resin is a cyanate ester compound obtained by reacting a phenol resin and a cyanogen halide. Specific examples thereof include benzene dicyanate, benzene tricyanato, naphthalene dicyanate, and biphenyl dicyanate. 2,2'-bis(4-cyanophenyl)propane, bis(4-cyanophenyl)methane, bis(3,5-dimethyl-4-cyanophenyl)methane, 2 ,2'-bis(3,5-dimethyl-4-cyanophenyl)propane, 2,2'-bis(4-cyanophenyl)ethane, 2,2'-bis(4 -Cyanatophenyl)hexafluoropropane, bis(4-cyanophenyl)terine, bis(4-cyanophenyl)thioether, phenolic novolac cyanate, phenol-dicyclopentadiene The hydroxyl group of the co-condensate is converted into a cyanate ester group, but it is not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used.
此外,合成方法記載於日本特開2005-264154號公報之氰酸酯化合物,係由於低吸濕性、阻燃性、介電特性優異,故特佳係作為氰酸酯化合物。 In addition, a cyanate ester compound whose synthesis method is described in Japanese Patent Application Laid-Open No. 2005-264154 is particularly preferred as a cyanate ester compound because it has low hygroscopicity, excellent flame retardancy and dielectric properties.
為了因應需要使氰酸基進行三聚化來形成均三環,氰酸酯樹脂中可含有環烷酸鋅、環烷酸鈷、環烷酸銅、環烷酸鉛、辛酸鋅、辛酸錫、乙醯丙酮鉛、順丁烯二酸二丁基錫等觸媒。 In order to meet the needs, the cyanate group can be trimerized to form homotrimeric Ring, cyanate ester resin may contain catalysts such as zinc naphthenate, cobalt naphthenate, copper naphthenate, lead naphthenate, zinc octoate, tin octoate, lead acetyl acetonate, dibutyl tin maleate, etc. .
相對於氰酸酯樹脂100質量份,觸媒較佳係使用0.0001至0.10質量份,較佳為0.00015至0.0015質量份。 It is preferable to use 0.0001 to 0.10 parts by mass of the catalyst relative to 100 parts by mass of the cyanate ester resin, and preferably 0.00015 to 0.0015 parts by mass.
〔聚伸苯基醚化合物〕 [Polyphenylene ether compound]
關於聚伸苯基醚化合物,就耐熱性與電氣特性之觀點而言,較佳為具有乙烯性不飽和鍵的聚伸苯基醚化合物,更佳為具有丙烯醯基、甲基丙烯醯基或苯乙烯結構的聚伸苯基醚化合物。市售品可列舉SA-9000(SABIC公司製之具有甲基丙 烯醯基的聚伸苯基醚化合物)和OPE-2St 1200(三菱瓦斯化學公司製之具有苯乙烯結構的聚伸苯基醚化合物)等。 Regarding the polyphenylene ether compound, from the viewpoint of heat resistance and electrical properties, a polyphenylene ether compound having an ethylenically unsaturated bond is preferred, and a polyphenylene ether compound having an acryl group, a methacryloyl group, or Polyphenylene ether compound with styrene structure. Examples of commercially available products include SA-9000 (manufactured by SABIC Co., Ltd., containing methylpropyl A polyphenylene ether compound with an enyl group) and OPE-2St 1200 (a polyphenylene ether compound with a styrene structure manufactured by Mitsubishi Gas Chemical Co., Ltd.), etc.
聚伸苯基醚化合物之數目平均分子量(Mn)較佳為500至5000,更佳為2000至5000,又更佳為2000至4000。若分子量未達500,則有無法獲得硬化物之耐熱性充分者的傾向。此外,若分子量大於5000,則熔融黏度變高、無法獲得充分的流動性,因而有易於變成成形不良的傾向。此外,有使反應性亦降低、硬化反應需要長時間、未反應的物質因未被納入硬化體系而增加、硬化物之玻璃轉移溫度降低、硬化物之耐熱性降低的傾向。 The number average molecular weight (Mn) of the polyphenylene ether compound is preferably 500 to 5000, more preferably 2000 to 5000, still more preferably 2000 to 4000. If the molecular weight is less than 500, there is a tendency that a cured product with sufficient heat resistance cannot be obtained. In addition, if the molecular weight exceeds 5,000, the melt viscosity becomes high and sufficient fluidity cannot be obtained, thereby tending to cause molding defects. In addition, the reactivity also decreases, the curing reaction takes a long time, the amount of unreacted substances increases because it is not included in the curing system, the glass transition temperature of the cured product decreases, and the heat resistance of the cured product tends to decrease.
聚伸苯基醚化合物之數目平均分子量若為500至5000,則可維持優異的介電特性並發揮優異的耐熱性及成形性等。又,於此,數目平均分子量就具體而言係可使用凝膠滲透層析術等進行測定。 If the number average molecular weight of the polyphenylene ether compound is 500 to 5000, it can maintain excellent dielectric properties and exhibit excellent heat resistance, formability, etc. In addition, here, the number average molecular weight can be specifically measured using gel permeation chromatography or the like.
就聚伸苯基醚化合物而言,可為藉由聚合反應而得者,亦可為使數目平均分子量10000至30000左右之高分子量的聚伸苯基醚化合物進行再分配反應而得者。此外,可藉由將此等作為原料並與甲基丙烯醯氯、丙烯醯氯、氯甲基苯乙烯等具有乙烯性不飽和鍵的化合物進行反應而賦予自由基聚合性。由再分配反應而得的聚伸苯基醚化合物,係例如於甲苯等溶劑中在酚化合物與自由基起始劑之存在下藉由將高分子量之聚伸苯基醚化合物加熱並進行再分配反應而得之。由如此之再分配反應而得的聚伸苯基醚化合物,係由於在分子鏈之兩末端具有源自「有利於硬化的酚系化合物」之羥基,故可進一步維持高耐熱性,並且,即使在經具有乙烯性不飽和鍵的化合物改質後,亦可在分子鏈之兩末端導入官能基,從而較佳。此外,由聚合反應而得的聚伸苯基醚化合物係顯示優異的流動性,從而較佳。 The polyphenylene ether compound may be obtained by polymerization reaction, or may be obtained by subjecting a high molecular weight polyphenylene ether compound having a number average molecular weight of approximately 10,000 to 30,000 to a redistribution reaction. In addition, radical polymerizability can be provided by reacting these as raw materials with compounds having an ethylenically unsaturated bond such as methacrylic acid chloride, acrylic acid chloride, and chloromethylstyrene. The polyphenylene ether compound obtained by the redistribution reaction is, for example, redistributed by heating a high molecular weight polyphenylene ether compound in a solvent such as toluene in the presence of a phenolic compound and a radical initiator. Obtained by reaction. The polyphenylene ether compound obtained by such a redistribution reaction has hydroxyl groups derived from "phenolic compounds that facilitate hardening" at both ends of the molecular chain, so it can further maintain high heat resistance and even After being modified with a compound having an ethylenically unsaturated bond, it is also preferable to introduce functional groups at both ends of the molecular chain. In addition, a polyphenylene ether compound obtained by a polymerization reaction is preferable because it exhibits excellent fluidity.
關於聚伸苯基醚化合物之分子量的調整,若在其為藉由聚合反應而得的聚伸苯基醚化合物之情況下,則可藉由調整聚合條件等而進行。此外,若在其為藉由再分配反應而得的聚伸苯基醚化合物之情況下,則可藉由調整再分配反應之條件等而調整所獲得的聚伸苯基醚化合物之分子量。更具體而言,可考慮調整在再分配反應中所使用的酚系化合物之調配量等。亦即,酚系化合物之調配量愈多,則獲得的聚伸苯基醚化合物之分子量愈低。此時,關於接受再分配反應之高分子量的聚伸苯基醚化合物,可使用聚(2,6-二甲基-1,4-伸苯基醚)等。此外,關於前述再分配反應所用的酚系化合物,並無特別限定,惟較佳係使用例如雙酚A、酚酚醛、甲酚酚醛等在分子中具有2個以上之酚性羥基的多官能酚系化合物。此等係可單獨使用,亦可組合使用2種以上。 The molecular weight of the polyphenylene ether compound can be adjusted by adjusting polymerization conditions, etc., if it is a polyphenylene ether compound obtained by a polymerization reaction. In addition, when it is a polyphenylene ether compound obtained by a redistribution reaction, the molecular weight of the obtained polyphenylene ether compound can be adjusted by adjusting the conditions of a redistribution reaction, etc. More specifically, adjustment of the compounding amount of the phenolic compound used in the redistribution reaction, etc. may be considered. That is, the greater the blending amount of the phenolic compound, the lower the molecular weight of the polyphenylene ether compound obtained. At this time, as the high molecular weight polyphenylene ether compound that undergoes the redistribution reaction, poly(2,6-dimethyl-1,4-phenylene ether) or the like can be used. In addition, the phenolic compound used in the aforementioned redistribution reaction is not particularly limited, but it is preferable to use polyfunctional phenols having two or more phenolic hydroxyl groups in the molecule, such as bisphenol A, phenol novolac, cresol novolac, etc. system compound. These systems can be used individually, or two or more types can be used in combination.
關於聚伸苯基醚化合物之含量,並無特別限定,惟相對於前述式(1)所示之化合物100質量份,較佳為5至1000質量份,更佳為10至750質量份。聚伸苯基醚化合物之含量若為上述範圍,則不僅耐熱性等優異,且可獲得充分發揮聚伸苯基醚化合物所具有的優異介電特性的硬化物,從而較佳。 The content of the polyphenylene ether compound is not particularly limited, but it is preferably 5 to 1000 parts by mass, and more preferably 10 to 750 parts by mass based on 100 parts by mass of the compound represented by formula (1). If the content of the polyphenylene ether compound is within the above range, it is preferable because it not only has excellent heat resistance and the like, but also can obtain a cured product that fully exhibits the excellent dielectric properties of the polyphenylene ether compound.
〔聚丁二烯及其改質物〕 [Polybutadiene and its modified products]
聚丁二烯及其改質物係意指在分子內具有聚丁二烯或源自聚丁二烯之結構的化合物。關於源自聚丁二烯之結構,可藉由氫化而將一部分或全部之不飽和鍵變更成單鍵。 Polybutadiene and its modified products refer to compounds having polybutadiene or a structure derived from polybutadiene in the molecule. Regarding the structure derived from polybutadiene, some or all of the unsaturated bonds can be changed into single bonds by hydrogenation.
關於聚丁二烯及其改質物,可列舉例如聚丁二烯、羥基末端聚丁二烯、末端(甲基)丙烯酸酯化聚丁二烯、羧酸末端聚丁二烯、胺末端聚丁二烯、苯乙烯丁二烯橡膠等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。此等之中,就介電特性之觀點而言,較佳為聚丁二烯或苯乙烯丁二烯橡膠。苯乙烯 丁二烯橡膠(SBR)可列舉例如:RICON-100、RICON-181、RICON-184(均為CRAY VALLEY公司製)、1,2-SBS(日本曹達公司製)等,聚丁二烯可列舉B-1000、B-2000、B-3000(均為日本曹達公司製)等。關於聚丁二烯及苯乙烯丁二烯橡膠之分子量,重量平均分子量較佳為500至10000,更佳為750至7500,又更佳為1000至5000。若在上述範圍之下限以下,則揮發量多,在製作預浸體時難以調整固形份,若在上述範圍之上限以上,則與其他硬化性樹脂之相溶性劣化。一般而言,在如雙順丁烯二醯亞胺或聚順丁烯二醯亞胺等含有氧或氮等雜原子的化合物之情況下,起因於其極性,難以確保與主要由烴所構成的化合物或者僅由烴所構成的化合物之低極性化合物的相溶性。另一方面,前述式(1)所示之化合物,係因其本身非積極導入氧或氮等雜原子的骨架設計,故其與具有低極性且低介電特性的材料或僅由烴所構成的化合物的相溶性亦優異。 Examples of polybutadiene and modified products thereof include polybutadiene, hydroxyl-terminated polybutadiene, terminal (meth)acrylated polybutadiene, carboxylic acid-terminated polybutadiene, and amine-terminated polybutadiene. Diene, styrene butadiene rubber, etc., but not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used. Among these, from the viewpoint of dielectric properties, polybutadiene or styrene-butadiene rubber is preferred. Styrene Examples of butadiene rubber (SBR) include RICON-100, RICON-181, RICON-184 (all manufactured by CRAY VALLEY Co., Ltd.), 1,2-SBS (manufactured by Nippon Soda Co., Ltd.), and polybutadiene. B-1000, B-2000, B-3000 (all made by Soda Corporation of Japan), etc. Regarding the molecular weight of polybutadiene and styrene-butadiene rubber, the weight average molecular weight is preferably 500 to 10,000, more preferably 750 to 7,500, and still more preferably 1,000 to 5,000. If it is below the lower limit of the above range, the amount of volatilization will be large, making it difficult to adjust the solid content when preparing a prepreg. If it is above the upper limit of the above range, the compatibility with other curable resins will deteriorate. Generally speaking, in the case of compounds containing heteroatoms such as oxygen or nitrogen, such as bismaleimide or polymaleimide, it is difficult to ensure that they are composed mainly of hydrocarbons due to their polarity. The compatibility of low polar compounds with compounds or compounds consisting only of hydrocarbons. On the other hand, the compound represented by the aforementioned formula (1) has a skeleton design in which heteroatoms such as oxygen or nitrogen are not actively introduced, so it is composed of materials with low polarity and low dielectric properties or only hydrocarbons. The compounds also have excellent compatibility.
關於聚丁二烯及其改質物之含量,並無特別限定,惟相對於前述式(1)所示之化合物100質量份,較佳為5至1000質量份,更佳為10至750質量份。聚丁二烯及其改質物若為上述範圍,則不僅耐熱性等優異,且可獲得充分發揮聚丁二烯及其改質物所具有的優異介電特性的硬化物,從而較佳。 The content of polybutadiene and its modified products is not particularly limited, but it is preferably 5 to 1000 parts by mass, more preferably 10 to 750 parts by mass based on 100 parts by mass of the compound represented by formula (1). . When the polybutadiene and its modified products are in the above range, not only are they excellent in heat resistance and the like, but a cured product that fully exhibits the excellent dielectric properties of the polybutadiene and its modified products can be obtained, which is preferable.
〔聚苯乙烯及其改質物〕 [Polystyrene and its modified substances]
聚苯乙烯及其改質物係意指在分子內具有聚苯乙烯或源自聚苯乙烯之結構的化合物。 Polystyrene and its modifications refer to compounds having polystyrene or a structure derived from polystyrene in the molecule.
關於聚苯乙烯及其改質物,可列舉例如:聚苯乙烯、苯乙烯與2-異丙烯基-2-唑啉共聚物(Epocros RPS-1005、RP-61均為日本觸媒公司製)、SEP(苯乙烯-伸乙基與丙烯共聚物:SEPTON 1020 KURARAY公司製)、SEPS(苯乙烯-伸乙基與丙烯-苯乙烯共聚物:SEPTON 2002、SEPTON 2004F、SEPTON 2005、SEPTON 2006、SEPTON 2063、SEPTON 2104均為KURARAY公司製)、SEEPS(苯乙烯-伸乙基/乙烯與丙烯-苯乙烯嵌段共聚物:SEPTON 4003、SEPTON 4044、SEPTON 4055、SEPTON 4077、SEPTON 4099均為KURARAY公司製)、SEBS(苯乙烯-伸乙基與丁烯-苯乙烯嵌段共聚物:SEPTON 8004、SEPTON 8006、SEPTON 8007L均為KURARAY公司製)、SEEPS-OH(在苯乙烯-伸乙基/乙烯與丙烯-苯乙烯嵌段共聚物之末端具有羥基的化合物:SEPTON HG252 KURARAY公司製)、SIS(苯乙烯-異戊二烯-苯乙烯嵌段共聚物:SEPTON 5125、SEPTON 5127均為KURARAY公司製)、氫化SIS(氫化苯乙烯-異戊二烯-苯乙烯嵌段共聚物:HYABRAR 7125F、HYABRAR 7311F均為KURARAY公司製)、SIBS(苯乙烯-異丁烯-苯乙烯嵌段共聚物:SIBSTAR073T、SIBSTAR102T、SIBSTAR103T(均為Kaneka公司製)、SEPTON V9827(KURARAY公司製))等,惟並非限於此等者。此外,此等係可使用1種,亦可使用複數種。聚苯乙烯及其改質物較佳為不具有不飽和鍵者,因而具有高耐熱性且難以氧化劣化。此外,聚苯乙烯及其改質物之重量平均分子量只要為10000以上則無特別限定,惟若過大,則與聚伸苯基醚化合物、重量平均分子量50至1000左右之低分子量成分、及重量平均分子量1000至5000左右之寡聚物成分的相溶性劣化,且難以確保混合及溶劑穩定性,從而較佳為10000至300000左右。 Examples of polystyrene and its modified products include: polystyrene, styrene and 2-isopropenyl-2- Oxazoline copolymer (Epocros RPS-1005, RP-61 are both manufactured by Nippon Shokubai Co., Ltd.), SEP (styrene-ethylidene and propylene copolymer: SEPTON 1020 manufactured by KURARAY Co., Ltd.), SEPS (styrene-ethylidene) With propylene-styrene copolymer: SEPTON 2002, SEPTON 2004F, SEPTON 2005, SEPTON 2006, SEPTON 2063, SEPTON 2104 are all made by KURARAY Co., Ltd.), SEEPS (styrene-ethylidene/ethylene and propylene-styrene block copolymer) Materials: SEPTON 4003, SEPTON 4044, SEPTON 4055, SEPTON 4077, SEPTON 4099 are all manufactured by KURARAY Co., Ltd.), SEBS (styrene-ethylidene and butylene-styrene block copolymer: SEPTON 8004, SEPTON 8006, SEPTON 8007L All manufactured by KURARAY Co., Ltd.), SEEPS-OH (a compound having a hydroxyl group at the end of a styrene-ethylidene/ethylene and propylene-styrene block copolymer: SEPTON HG252 manufactured by KURARAY Co., Ltd.), SIS (styrene-isopentyl) Diene-styrene block copolymer: SEPTON 5125, SEPTON 5127 are both manufactured by KURARAY Co., Ltd.), hydrogenated SIS (hydrogenated styrene-isoprene-styrene block copolymer: HYABRAR 7125F, HYABRAR 7311F are both manufactured by KURARAY Co., Ltd. (manufactured by Kaneka Co., Ltd.), SIBS (styrene-isobutylene-styrene block copolymer: SIBSTAR073T, SIBSTAR102T, SIBSTAR103T (all produced by Kaneka Co., Ltd.), SEPTON V9827 (manufactured by KURARAY Co., Ltd.)), etc., but are not limited to these. In addition, one type of these systems may be used, or a plurality of types may be used. Polystyrene and its modified products preferably do not have unsaturated bonds, so they have high heat resistance and are difficult to be oxidized and deteriorated. In addition, the weight average molecular weight of polystyrene and its modified products is not particularly limited as long as it is 10,000 or more. However, if it is too large, it will cause polyphenylene ether compounds, low molecular weight components with a weight average molecular weight of about 50 to 1,000, and weight average The compatibility of oligomer components with a molecular weight of about 1,000 to 5,000 deteriorates and it is difficult to ensure mixing and solvent stability, so the molecular weight is preferably about 10,000 to 300,000.
關於聚苯乙烯及其改質物之含量,並無特別限定,惟相對於前述式(1)所示之化合物100質量份,較佳為5至1000質量份,更佳為10至750質量份。苯乙烯及其改質物若為上述範圍,則不僅耐熱性等優異,且可獲得充分發揮聚苯乙烯及其改質物所具有的優異介電特性的硬化物,從而較佳。 The content of polystyrene and its modified products is not particularly limited, but it is preferably 5 to 1000 parts by mass, and more preferably 10 to 750 parts by mass based on 100 parts by mass of the compound represented by formula (1). When the content of styrene and its modified products is in the above range, it is preferable because it not only has excellent heat resistance and the like, but also can obtain a cured product that fully exhibits the excellent dielectric properties of polystyrene and its modified products.
本實施型態之硬化性樹脂組成物係藉由將上述各成分以預定比率調製而獲得,在130至180℃預備硬化30至500秒之範圍,更藉由在150至200℃進行後硬化2至15小時而進行充分的硬化反應,從而獲得本實施型態之硬化物。此外,亦可使硬化性樹脂組成物之成分均勻地分散或溶解於溶劑等,除去溶劑後使其硬化。 The curable resin composition of this embodiment is obtained by modulating the above-mentioned components in a predetermined ratio, pre-curing at 130 to 180°C for 30 to 500 seconds, and further post-curing at 150 to 200°C for 2 seconds. The hardening reaction proceeds sufficiently until 15 hours to obtain the hardened product of this embodiment. In addition, the components of the curable resin composition may be uniformly dispersed or dissolved in a solvent or the like, and then the solvent may be removed and then cured.
本實施型態之硬化性樹脂組成物的調製方法並無特別限定,惟可將各成分均勻地混合,亦可預聚合化。例如,在硬化促進劑或聚合起始劑之存在下或不存在下、溶劑之存在下或不存在下,對調配有前述式(1)所示之順丁烯二醯亞胺化合物及其他之化合物的混合物加熱,藉此而進行預聚合化。同樣地,可追加胺化合物、具有乙烯性不飽和鍵的化合物、式(1)所示之順丁烯二醯亞胺化合物以外之順丁烯二醯亞胺化合物、氰酸酯化合物、聚丁二烯及其改質物、聚苯乙烯及其改質物等化合物、無機填充劑、及其他添加劑並預聚合化。關於各成分之混合或預聚合化,若在溶劑之不存在下則例如使用擠出機、捏合機、輥壓機等,若在溶劑之存在下則使用附攪拌裝置之反應器等。 The preparation method of the curable resin composition of this embodiment is not particularly limited, as long as each component can be uniformly mixed or pre-polymerized. For example, in the presence or absence of a hardening accelerator or a polymerization initiator, in the presence or absence of a solvent, the maleimide compound represented by the aforementioned formula (1) and other The mixture of compounds is heated to perform prepolymerization. Similarly, an amine compound, a compound having an ethylenically unsaturated bond, a maleimide compound other than the maleimide compound represented by formula (1), a cyanate ester compound, and a polybutylene compound may be added. Dienes and their modifications, polystyrene and its modifications and other compounds, inorganic fillers, and other additives are prepolymerized. Regarding the mixing or prepolymerization of each component, if a solvent is not present, an extruder, a kneader, a roller press, etc. are used, and if a solvent is present, a reactor equipped with a stirring device, etc. is used.
關於均勻混合的方法,在50至100℃之範圍內的溫度,使用捏合機、輥壓機、行星攪拌機等裝置進行混煉,而獲得均勻的樹脂組成物。亦可將獲得的樹脂組成物粉碎後,以壓錠機等成型機成型為圓柱的錠狀,或者製成顆粒狀之粉體或成粉狀之成型體,或者將此等組成物熔融在表面支撐體上而成型成0.05mm至10mm之厚度的片狀,從而獲得硬化性樹脂組成物成型體。獲得的成型體在0至20℃成為不黏的成型體,即使在-25至0℃保存1週以上,其流動性、硬化性亦幾乎不會降低。 Regarding the method of uniform mixing, a uniform resin composition is obtained by kneading at a temperature in the range of 50 to 100° C. using a kneader, a roller press, a planetary mixer, or the like. The obtained resin composition can also be pulverized and then molded into a cylindrical ingot shape using a molding machine such as a tablet press, or can be made into granular powder or a powdery molded body, or the composition can be melted and supported on the surface. The body is formed into a sheet with a thickness of 0.05 mm to 10 mm, thereby obtaining a curable resin composition molded body. The obtained molded body becomes non-sticky at 0 to 20°C, and its fluidity and hardening properties hardly decrease even if it is stored at -25 to 0°C for more than one week.
可使用轉送模製成型機、壓縮模製成型機,將獲得的成型體成型為硬化物。 The obtained molded body can be molded into a hardened product using a transfer molding machine or a compression molding machine.
本實施型態之硬化性樹脂組成物中亦可添加有機溶劑製成清漆(varnish)狀的組成物(以下簡稱為清漆)。因應需要,使本實施型態之硬化性樹脂組成物溶解在甲苯、二甲苯、丙酮、甲基乙基酮、甲基異丁基酮、二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯啶酮等溶劑中,製成清漆,使其浸漬在玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維、紙等基材並加熱乾燥,將獲得的預浸體熱壓成型,藉此可獲得本實施型態之硬化性樹脂組成物的硬化物。此時,本實施型態之硬化性樹脂組成物與該溶劑之混合物中,溶劑的使用量為10至70重量%,較佳為15至70重量%。此外,若為液狀組成物,則亦可直接藉由例如RTM方式而獲得含有碳纖維的硬化性樹脂硬化物。 An organic solvent may be added to the curable resin composition of this embodiment to form a varnish-like composition (hereinafter referred to as varnish). If necessary, the curable resin composition of this embodiment is dissolved in toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethyl formamide, dimethyl acetamide, In N-methylpyrrolidone and other solvents, make varnish, impregnate it in glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber, paper and other base materials, and heat and dry the obtained prepreg. By performing body hot press molding, a cured product of the curable resin composition of this embodiment can be obtained. At this time, in the mixture of the curable resin composition of this embodiment and the solvent, the usage amount of the solvent is 10 to 70% by weight, preferably 15 to 70% by weight. In addition, if it is a liquid composition, a curable resin cured product containing carbon fibers can also be obtained directly by, for example, RTM method.
此外,亦可將本實施型態之硬化性組成物作為薄膜型組成物的改質劑來使用。具體而言,可使用於B-階段中之使柔韌性等提升之情況。如此之薄膜型的樹脂組成物,係將本實施型態之硬化性樹脂組成物作為前述硬化性樹脂組成物清漆而塗佈在剝離薄膜上,在加熱下除去溶劑後,藉由進行B階段化,而獲得片狀的接著劑。該片狀接著劑可作為多層基板等中之層間絕緣層來使用。 In addition, the curable composition of this embodiment can also be used as a modifier of a film-type composition. Specifically, it can be used to improve flexibility in the B-stage. Such a film-type resin composition is obtained by applying the curable resin composition of the present embodiment as the curable resin composition varnish on a release film, removing the solvent under heating, and then performing B-stage conversion. , and obtain a sheet-like adhesive. This sheet-like adhesive can be used as an interlayer insulating layer in multilayer substrates and the like.
本實施型態之硬化性樹脂組成物亦可藉由加熱熔融、低黏度化,並使之含浸於玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維等強化纖維中而獲得預浸體。其具體例可列舉例如:E玻璃布、D玻璃布、S玻璃布、Q玻璃布、球狀玻璃布、NE玻璃布、及T玻璃布等玻璃纖維,玻璃以外之無機物的纖維和聚對苯二甲醯對苯二胺(Kevlar(註冊商標)、杜邦公司製)、全芳香族聚醯胺、聚酯、聚對苯并唑、聚醯亞胺及碳纖維等有機纖維,惟並非限定於此等。關於基材之形狀,並無特別限定,惟可列舉例如:織布、不織布、粗紗、短切原絲氈等。此外,關於織布的編織方法,已知有平紋織物、方平組織織物、斜紋織 物,可依據作為目的之用途和性能從此等習知者中適宜選擇使用。此外,較佳使用經開纖處理的織布或以矽烷偶合劑等進行表面處理的玻璃織布。關於基材之厚度,並無特別限定,惟較佳為0.01至0.4mm左右。此外,亦可藉由使強化纖維浸漬於前述清漆並進行加熱乾燥而獲得預浸體。 The curable resin composition of this embodiment can also be preformed by heating, melting, reducing the viscosity, and impregnating it with reinforcing fibers such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, and alumina fiber. Dip body. Specific examples thereof include glass fibers such as E glass cloth, D glass cloth, S glass cloth, Q glass cloth, spherical glass cloth, NE glass cloth, and T glass cloth, inorganic fibers other than glass, and polyparaphenylene. Dimethylphenylenediamine (Kevlar (registered trademark), manufactured by DuPont), fully aromatic polyamide, polyester, polyparabenzo Organic fibers such as azole, polyimide and carbon fiber, but are not limited to these. The shape of the base material is not particularly limited, but examples include woven fabric, nonwoven fabric, roving, chopped strand mat, etc. In addition, as for the weaving method of the woven fabric, plain weave fabric, square weave fabric, and twill weave fabric are known, and those skilled in the art can select and use them appropriately according to the intended use and performance. In addition, it is preferable to use a fiber-opened woven fabric or a glass woven fabric surface-treated with a silane coupling agent or the like. The thickness of the base material is not particularly limited, but is preferably about 0.01 to 0.4 mm. In addition, a prepreg can also be obtained by impregnating reinforcing fibers in the varnish and drying them by heating.
此外,亦可使用上述預浸體製造積層板。積層板只要具備1片以上的預浸體則無特別限定,可具有任何其他層。關於積層板之製造方法,並無特別限定,可適宜使用一般習知的方法。例如,在進行覆金屬箔之積層板之成型時,可使用多段壓機、多段真空壓機、連續成型機、高壓釜成型機等,藉由將上述預浸體彼此積層並加熱加壓成型而獲得積層板。此時,加熱溫度並無特別限定,惟較佳為65至300℃,更佳為120至270℃。此外,加壓壓力並無特別限定,惟若加壓過大,則難以調整積層板之樹脂的固形份且品質不穩定,此外,若壓力過小,則會出現氣泡和積層間之密著性變差,因此,較佳為2.0至5.0MPa,更佳為2.5至4.0MPa。本實施型態之積層板因具備由金屬箔所構成之層,故可適宜作為後述覆金屬箔之積層板來使用。 In addition, the above-mentioned prepreg can also be used to produce a laminated board. The laminated board is not particularly limited as long as it contains one or more prepregs, and may have any other layers. The manufacturing method of the laminated board is not particularly limited, and generally known methods can be suitably used. For example, when molding metal foil-coated laminated boards, a multi-stage press, a multi-stage vacuum press, a continuous molding machine, an autoclave molding machine, etc. can be used to laminate the above-mentioned prepregs and heat and press them. Get laminate boards. At this time, the heating temperature is not particularly limited, but is preferably 65 to 300°C, more preferably 120 to 270°C. In addition, the pressing pressure is not particularly limited. However, if the pressure is too high, it will be difficult to adjust the solid content of the resin in the laminate and the quality will be unstable. In addition, if the pressure is too small, bubbles will occur and the adhesion between the laminates will deteriorate. , therefore, it is preferably 2.0 to 5.0MPa, and more preferably 2.5 to 4.0MPa. Since the laminated board of this embodiment has a layer made of metal foil, it can be suitably used as a metal foil-clad laminated board to be described later.
將上述預浸體裁切成所期望的形狀,依據需要與銅箔等積層後,一邊以壓成型法或高壓釜成型法、片材捲繞成型法等對積層物施壓,一邊使硬化性樹脂組成物加熱硬化,藉此可獲得電氣電子用積層板(印刷配線板)、碳纖維強化材。 The above-mentioned prepreg is cut into a desired shape and laminated with copper foil or the like as necessary, and then the curable resin is added to the laminated product while applying pressure to the laminate using a press molding method, an autoclave molding method, a sheet winding molding method, or the like. By heating and hardening the composition, electrical and electronic laminates (printed wiring boards) and carbon fiber reinforced materials can be obtained.
本實施型態之硬化性樹脂組成物亦可作成樹脂片。關於從本實施型態之硬化性樹脂組成物獲得樹脂片之方法,可列舉例如:將硬化性樹脂組成物塗佈在支撐薄膜(支撐體)上後使其乾燥,在支撐薄膜上形成樹脂組成物層的方法。在將本實施型態之硬化性樹脂組成物使用於樹脂片之情況下,較佳係該薄膜在真空積層法中之積層的溫度條件(70℃至140℃)下軟化,在與電路基板之積層 之同時,重要的是顯示出可達成在電路基板中存在的導通孔或通孔內填充樹脂的流動性(樹脂流動),並以表現如此特性的方式來調配前述各成分。又,在所得的樹脂片和電路基板(覆銅積層板等)中,不會發生由相分離等所致之顯示出局部性相異的特性值之現象,為了在任意部位表現一定的性能而要求外觀均勻性。 The curable resin composition of this embodiment can also be made into a resin sheet. An example of a method for obtaining a resin sheet from the curable resin composition of this embodiment is to apply the curable resin composition on a support film (support) and then dry it to form a resin composition on the support film. object layer method. When the curable resin composition of this embodiment is used in a resin sheet, it is preferable that the film is softened under the temperature conditions of lamination (70°C to 140°C) in the vacuum lamination method, and is in contact with the circuit substrate. Lamination At the same time, it is important to demonstrate the fluidity (resin flow) that can be achieved by filling resin in via holes or through-holes existing in the circuit board, and to prepare each of the aforementioned components in a manner that exhibits such characteristics. In addition, the resulting resin sheet and circuit board (copper-clad laminate, etc.) do not exhibit locally different characteristic values due to phase separation, etc., and are designed to express certain performance at any location. Appearance uniformity is required.
於此,電路基板之貫通孔的直徑為0.1至0.5mm、深度為0.1至1.2mm,較佳係在該範圍中能夠進行樹脂填充。又,在將電路基板之兩面進行積層之情況下,期望使貫通孔填充1/2左右。 Here, the diameter of the through hole of the circuit board is 0.1 to 0.5 mm, and the depth is 0.1 to 1.2 mm. It is preferable that resin filling can be performed within this range. Moreover, when laminating both sides of a circuit board, it is desirable to fill approximately 1/2 of the through hole.
關於製造前述樹脂片之具體方法,可列舉如:調配有機溶劑而調製經清漆化的樹脂組成物後,將前述清漆化的樹脂組成物塗佈在支撐薄膜(Y)之表面,藉由進一步加熱或吹熱風等而乾燥有機溶劑以形成樹脂組成物層(X)的方法。 Specific methods for producing the resin sheet include: preparing a varnished resin composition by blending an organic solvent, coating the varnished resin composition on the surface of the support film (Y), and further heating the resin sheet. Or a method of drying the organic solvent by blowing hot air or the like to form the resin composition layer (X).
關於此處所使用的有機溶劑,較佳係使用例如丙酮、甲基乙基酮、環己酮等酮類、乙酸乙酯、乙酸丁酯、乙酸賽璐蘇、丙二醇單甲醚乙酸酯、卡必醇乙酸酯等乙酸酯類、賽璐蘇、丁基卡必醇等卡必醇類、甲苯、二甲苯等芳香族烴類、二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯啶酮等,此外,較佳係以不揮發分30至60質量%之比率來使用。 The organic solvent used here is preferably ketones such as acetone, methyl ethyl ketone, and cyclohexanone, ethyl acetate, butyl acetate, cellulosine acetate, propylene glycol monomethyl ether acetate, and carboxylic acid. Acetates such as bitol acetate, carbitols such as cellulose and butylcarbitol, aromatic hydrocarbons such as toluene and xylene, dimethylformamide, dimethylacetamide, N - Methylpyrrolidone, etc. In addition, it is preferably used in a ratio of 30 to 60% by mass of non-volatile matter.
又,所形成的前述樹脂組成物層(X)之厚度必須為導體層之厚度以上。由於電路基板所具有的導體層之厚度在5至70μm之範圍,因此,前述樹脂組成物層(X)之厚度較佳係具有10至100μm之厚度。又,本實施型態中之前述樹脂組成物層(X)可被後述保護薄膜所保護。藉由被保護薄膜所保護,可防止對於樹脂組成物層表面之灰塵附著和劃痕。 In addition, the thickness of the resin composition layer (X) formed must be equal to or greater than the thickness of the conductor layer. Since the thickness of the conductor layer of the circuit substrate is in the range of 5 to 70 μm, the thickness of the resin composition layer (X) is preferably in the range of 10 to 100 μm. In addition, in this embodiment, the aforementioned resin composition layer (X) can be protected by a protective film described later. By being protected by the protective film, dust adhesion and scratches on the surface of the resin composition layer can be prevented.
關於前述支撐薄膜及保護薄膜,可列舉:聚乙烯、聚丙烯、聚氯乙烯等聚烯烴、聚對酞酸乙二酯(PET)、聚萘二甲酸乙二酯等聚酯、聚碳酸酯、聚醯亞胺,以及脫模紙或銅箔、鋁箔等金屬箔等。又,對於支撐薄膜及保護薄膜可實施MAD處理、電暈處理及脫模處理。支撐薄膜之厚度並無特別限定,為10至150μm,較佳係在25至50μm之範圍內使用。此外,保護薄膜之厚度較佳為1至40μm。 Examples of the support film and protective film include polyolefins such as polyethylene, polypropylene, and polyvinyl chloride, polyesters such as polyethylene terephthalate (PET), and polyethylene naphthalate, and polycarbonates. Polyimide, release paper or metal foils such as copper foil and aluminum foil. In addition, the support film and protective film can be subjected to MAD treatment, corona treatment and demoulding treatment. The thickness of the supporting film is not particularly limited, but is 10 to 150 μm, and is preferably used in the range of 25 to 50 μm. In addition, the thickness of the protective film is preferably 1 to 40 μm.
前述支撐薄膜(Y),係在積層於電路基板後或在藉由加熱硬化而形成絕緣層後剝離。在構成樹脂片之樹脂組成物層加熱硬化後,若剝離支撐薄膜(Y),則可防止硬化步驟中之灰塵等之附著。在硬化後進行剝離之情況下,則預先對支撐薄膜實施脫模處理。 The support film (Y) is peeled off after being laminated on the circuit board or after forming an insulating layer by heating and hardening. After the resin composition layer constituting the resin sheet is heated and hardened, if the support film (Y) is peeled off, dust and the like can be prevented from adhering during the hardening step. When peeling after hardening, the support film is subjected to a release treatment in advance.
又,可從依據前述而得的樹脂片製造多層印刷電路基板。例如,在經保護薄膜保護前述樹脂組成物層(X)之情況下,將此等剝離後,將前述樹脂組成物之層(X)以直接接觸電路基板之方式在電路基板之單面或兩面藉由例如真空積層法積層。積層之方法可為分批式,亦可為使用輥壓機的連續式。此外,依據需要,可在進行積層前依據需要而加熱(預熱)樹脂片及電路基板。積層之條件,較佳係將壓附溫度(積層溫度)設為70至140℃,較佳係將壓附壓力設為1至11kgf/cm2(9.8×104至107.9×104N/m2),並且較佳係在空氣壓20mmHg(26.7hPa)以下之減壓下進行積層。 Moreover, a multilayer printed circuit board can be manufactured from the resin sheet obtained as mentioned above. For example, when the resin composition layer (X) is protected by a protective film, after peeling off the resin composition layer (X), the resin composition layer (X) is directly contacted with the circuit substrate on one or both sides of the circuit substrate. Laminated by, for example, a vacuum lamination method. The laminating method can be a batch type or a continuous type using a roller press. In addition, if necessary, the resin sheet and the circuit board may be heated (preheated) as necessary before lamination. As for the lamination conditions, the pressing temperature (lamination temperature) is preferably set to 70 to 140°C, and the pressing pressure is preferably set to 1 to 11kgf/cm 2 (9.8×10 4 to 107.9×10 4 N/m 2 ), and it is preferable to laminate under reduced pressure of 20mmHg (26.7hPa) or less.
此外,可使用本實施型態之硬化性樹脂組成物製造半導體裝置。半導體裝置可列舉例如:DIP(雙列直插封裝)、QFP(四方扁平封裝)、BGA(球柵陣列)、CSP(微晶尺寸封裝)、SOP(小外形封裝)、TSOP(薄小外形封裝)、TQFP(薄四方扁平封裝)等。 In addition, a semiconductor device can be manufactured using the curable resin composition of this embodiment. Examples of semiconductor devices include: DIP (dual in-line package), QFP (quad flat package), BGA (ball grid array), CSP (microcrystalline package), SOP (small outline package), TSOP (thin small outline package) ), TQFP (Thin Quad Flat Package), etc.
本實施型態之硬化性樹脂組成物及其硬化物可用於廣泛的領域。具體而言,可使用於成型材料、接著劑、複合材料、塗料等各種用途。由於本實施型態記載之硬化性樹脂組成物的硬化物顯示優異的耐熱性與介電特性,故較佳係使用於半導體元件用密封材、液晶顯示元件用密封材、有機EL元件用密封材、積層板(印刷配線板、BGA用基板、組裝基板等)等之電氣電子零件和碳纖維強化塑膠、玻璃纖維強化塑膠等輕量高強度結構材用複合材料、3D列印等。 The curable resin composition and its cured product according to this embodiment can be used in a wide range of fields. Specifically, it can be used in various applications such as molding materials, adhesives, composite materials, and coatings. Since the cured product of the curable resin composition described in this embodiment shows excellent heat resistance and dielectric properties, it is preferably used as a sealing material for semiconductor elements, a sealing material for liquid crystal display elements, and a sealing material for organic EL elements. , composite materials for electrical and electronic parts such as laminated boards (printed wiring boards, BGA substrates, assembly substrates, etc.) and lightweight high-strength structural materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics, 3D printing, etc.
[實施例] [Example]
其次,依據實施例更具體說明本發明。以下,除非另有說明,否則份係指質量份。另外,本發明不限於此等實施例。 Next, the present invention will be described in more detail based on examples. Hereinafter, parts refer to parts by mass unless otherwise stated. In addition, the present invention is not limited to these embodiments.
以下記載實施例中使用的各種分析方法。 Various analysis methods used in the Examples are described below.
‧GPC(凝膠滲透層析術)分析 ‧GPC (gel permeation chromatography) analysis
使用聚苯乙烯標準液藉由聚苯乙烯換算而算出重量平均分子量(Mw)及數目平均分子量(Mn)。 The weight average molecular weight (Mw) and the number average molecular weight (Mn) were calculated in polystyrene conversion using a polystyrene standard solution.
GPC:在線脫氣裝置(DGU-20A3R)、二元移液裝置(LC-20AD)、自動進樣器(SIL-20AHT)、示差折射率檢測器(RID-20A)、管柱烘箱(CTO-20A)、系統控制器(CBM-20A)(均為島津製作所製) GPC: Online degassing device (DGU-20A3R), binary pipetting device (LC-20AD), automatic sampler (SIL-20AHT), differential refractive index detector (RID-20A), column oven (CTO- 20A), system controller (CBM-20A) (both manufactured by Shimadzu Corporation)
管柱:Shodex KF-603×1、KF-602.5×1、KF-602×1、KF-601×1(均為昭和電工公司製) Pipe string: Shodex KF-603×1, KF-602.5×1, KF-602×1, KF-601×1 (all manufactured by Showa Denko Co., Ltd.)
保護管柱:Shodex KF-G 4A(昭和電工公司製) Protection column: Shodex KF-G 4A (manufactured by Showa Denko Co., Ltd.)
合併洗脫液:四氫呋喃 Combined eluents: tetrahydrofuran
流速:1.5ml/min. Flow rate: 1.5ml/min.
管柱溫度:40℃ Tube string temperature: 40℃
檢測:RI(示差折射檢測器) Detection: RI (differential refraction detector)
‧1H-NMR分析 ‧ 1 H-NMR analysis
裝置:核磁共振裝置(JNM-ECS400)日本電子股份有限公司製 Equipment: Nuclear Magnetic Resonance Equipment (JNM-ECS400) manufactured by Japan Electronics Co., Ltd.
〔實施例1〕 [Example 1]
在安裝有溫度計、冷卻管、攪拌機、迪安-斯塔克(Dean-Stark)裝置的燒瓶中,饋入2,6-二甲基苯胺24.3份、α,α,α',α'-四甲基-1,3-苯二甲醇136份、甲苯100份、活性黏土35份,一邊以共沸脫水除去所產生的水,一邊在內溫110至135℃反應1.5小時。其後,一邊萃取甲苯,一邊將內溫升溫至210℃為止,反應4小時。靜置冷卻後,使萃取出的甲苯返回系統,新加入甲苯200份。藉由過濾而除去活性黏土,獲得含有下述式(6)所示之胺化合物的甲苯溶液(T-1)。獲得的胺化合物的GPC圖表示於圖1。 In a flask equipped with a thermometer, a cooling tube, a stirrer, and a Dean-Stark device, 24.3 parts of 2,6-dimethylaniline, α,α,α',α'-tetrahydrofuran were added. 136 parts of methyl-1,3-benzenedimethanol, 100 parts of toluene, and 35 parts of activated clay were reacted at an internal temperature of 110 to 135°C for 1.5 hours while removing the water produced by azeotropic dehydration. Thereafter, while extracting toluene, the internal temperature was raised to 210°C, and the reaction was carried out for 4 hours. After cooling, the extracted toluene is returned to the system, and 200 parts of toluene are added. The activated clay was removed by filtration, and a toluene solution (T-1) containing an amine compound represented by the following formula (6) was obtained. The GPC chart of the obtained amine compound is shown in Figure 1 .
繼而,在安裝有溫度計、冷卻管、攪拌機、迪安-斯塔克裝置的燒瓶中,加入甲苯100份、順丁烯二醯酸酐29.4份、甲磺酸5.4份,一邊將內溫保持110℃,一邊以4小時滴加T-1。更且,在110℃以9小時進行下述式(6)所示之胺的烯烴部之聚合反應、及胺基之順丁烯二醯亞胺化反應。靜置冷卻後,加入甲苯200份,以水100份洗滌有機層5次。加熱減壓下,藉由餾去溶劑,而獲得作為褐色固形樹脂的下述式(7)所示之順丁烯二醯亞胺化合物(M-1)133份。將獲得的順丁烯二醯亞胺化合物的GPC圖表示於圖2。數目平均分子量(Mn)為2082、重量平均分子量(Mw)為3169。此外,將所得的順丁烯二醯亞胺化合物之1H-NMR圖表(重氯仿)示於圖3。在1H-NMR圖表之6.85ppm觀察到源自順丁烯二醯亞胺基的訊號。 Then, 100 parts of toluene, 29.4 parts of maleic anhydride, and 5.4 parts of methanesulfonic acid were added to a flask equipped with a thermometer, a cooling tube, a stirrer, and a Dean-Stark device, while maintaining the internal temperature at 110°C. , while adding T-1 dropwise for 4 hours. Furthermore, the polymerization reaction of the olefin part of the amine represented by the following formula (6) and the maleide imidization reaction of the amine group were performed at 110° C. for 9 hours. After leaving to cool, 200 parts of toluene was added, and the organic layer was washed 5 times with 100 parts of water. The solvent was distilled off under heating and reduced pressure, thereby obtaining 133 parts of a maleimide compound (M-1) represented by the following formula (7) as a brown solid resin. The GPC chart of the obtained maleimide compound is shown in Figure 2 . The number average molecular weight (Mn) is 2082, and the weight average molecular weight (Mw) is 3169. In addition, the 1 H-NMR chart (heavy chloroform) of the obtained maleimide compound is shown in FIG. 3 . A signal originating from the maleimide group was observed at 6.85 ppm in the 1 H-NMR chart.
〔實施例2〕 [Example 2]
在安裝有溫度計、冷卻管、攪拌機、迪安-斯塔克裝置的燒瓶中,饋入2,6-二異丙基苯胺35.4份、α,α,α',α'-四甲基-1,3-苯二甲醇136份、甲苯100份、活性黏土35份,一邊以共沸脫水除去產生的水,一邊在內溫110至135℃反應2小時。其後,一邊萃取甲苯,一邊將內溫升溫至210℃為止,反應9小時。靜置冷卻後,使萃取出的甲苯返回系統,新加入甲苯200份。藉由過濾而除去活性黏土,獲得含有下述式(8)所示之胺化合物的甲苯溶液(T-2)。將獲得的胺化合物的GPC圖表示於圖4。 In a flask equipped with a thermometer, cooling tube, stirrer, and Dean Stark device, 35.4 parts of 2,6-diisopropylaniline and α,α,α',α'-tetramethyl-1 were fed , 136 parts of 3-benzenedimethanol, 100 parts of toluene, and 35 parts of activated clay were reacted at an internal temperature of 110 to 135°C for 2 hours while removing the water produced by azeotropic dehydration. Thereafter, while extracting toluene, the internal temperature was raised to 210°C, and the reaction was carried out for 9 hours. After cooling, the extracted toluene is returned to the system, and 200 parts of toluene are added. The activated clay was removed by filtration, and a toluene solution (T-2) containing an amine compound represented by the following formula (8) was obtained. The GPC chart of the obtained amine compound is shown in Figure 4 .
繼而,在安裝有溫度計、冷卻管、攪拌機、迪安-斯塔克裝置的燒瓶中,加入甲苯100份、順丁烯二醯酸酐29.4份、甲磺酸5.4份,一邊將內溫保持在110℃,一邊以2小時滴加T-2。更且,在110℃以10小時進行下述式(8)所示之胺化合物的烯烴部之聚合反應、及胺基之順丁烯二醯亞胺化反應。靜置冷卻後,加入甲苯200份,以水100份洗滌有機層5次。加熱減壓下,藉由餾去溶劑,而獲得作為褐色固形樹脂的下述式(9)所示之順丁烯二醯亞胺化合物(M-2)125份。將獲得 的順丁烯二醯亞胺化合物的GPC圖表示於圖5。數目平均分子量(Mn)為2007、重量平均分子量(Mw)為3301。此外,將所得的順丁烯二醯亞胺化合物之1H-NMR圖表(重氯仿)示於圖6。在1H-NMR圖表之6.85ppm觀察到源自順丁烯二醯亞胺基的訊號。 Then, 100 parts of toluene, 29.4 parts of maleic anhydride, and 5.4 parts of methanesulfonic acid were added to a flask equipped with a thermometer, a cooling tube, a stirrer, and a Dean-Stark device, while maintaining the internal temperature at 110°C. ℃, while adding T-2 dropwise for 2 hours. Furthermore, the polymerization reaction of the olefin part of the amine compound represented by the following formula (8) and the maleide imidization reaction of the amine group were performed at 110° C. for 10 hours. After leaving to cool, 200 parts of toluene was added, and the organic layer was washed 5 times with 100 parts of water. The solvent was distilled off under heating and reduced pressure, thereby obtaining 125 parts of a maleimide compound (M-2) represented by the following formula (9) as a brown solid resin. The GPC chart of the obtained maleimide compound is shown in Figure 5 . The number average molecular weight (Mn) is 2007, and the weight average molecular weight (Mw) is 3301. In addition, the 1 H-NMR chart (heavy chloroform) of the obtained maleimide compound is shown in FIG. 6 . A signal originating from the maleimide group was observed at 6.85 ppm in the 1 H-NMR chart.
〔合成例1〕 [Synthesis example 1]
在裝有溫度計、冷卻管、攪拌機、迪安-斯塔克裝置的燒瓶,饋入2,6-二甲基苯胺48.5份、α,α,α',α'-四甲基-1,3-苯二甲醇155.4份、甲苯100份、活性黏土30.6份,一邊以共沸脫水除去甲苯及產生的水,一邊以2小時將內溫升溫至210℃為止,反應3小時(將GPC圖表示於圖7)。將內溫冷卻至120℃為止後,加入2,6-二甲基苯胺145.4份,在220℃反應3小時。靜置冷卻後,使萃取出的甲苯返回系統,新加入甲苯200份。藉由過濾而除去活性黏土,並餾去溶劑及過量的2,6-二甲基苯胺,而獲得作為褐色固形樹脂的下述式(10)所示之胺化合物(A-1)207份 (胺當量:272.7g/eq.)。獲得的胺化合物的GPC圖表示於圖7。數目平均分子量(Mn)為1048、重量平均分子量(Mw)為1252。 In a flask equipped with a thermometer, cooling tube, stirrer, and Dean Stark apparatus, 48.5 parts of 2,6-dimethylaniline and α,α,α',α'-tetramethyl-1,3 are fed - 155.4 parts of benzenedimethanol, 100 parts of toluene, and 30.6 parts of activated clay, while removing toluene and the generated water by azeotropic dehydration, raise the internal temperature to 210°C for 2 hours, and react for 3 hours (the GPC chart is shown in Figure 7). After cooling the internal temperature to 120°C, 145.4 parts of 2,6-dimethylaniline was added and the reaction was carried out at 220°C for 3 hours. After cooling, the extracted toluene is returned to the system, and 200 parts of toluene are added. The activated clay was removed by filtration, and the solvent and excess 2,6-dimethylaniline were distilled off to obtain 207 parts of the amine compound (A-1) represented by the following formula (10) as a brown solid resin. (Amine equivalent: 272.7g/eq.). The GPC chart of the obtained amine compound is shown in Figure 7 . The number average molecular weight (Mn) is 1048, and the weight average molecular weight (Mw) is 1252.
〔合成例2〕 [Synthesis example 2]
在安裝有溫度計、冷卻管、攪拌機、迪安-斯塔克裝置的燒瓶,加入甲苯50份、順丁烯二醯酸酐53.9份、甲磺酸2份,一邊保持回流狀態,一邊以1小時滴加A-1之甲苯及N-甲基吡咯啶酮(NMP)溶液(A-1:100份、甲苯:75份、NMP25份)。在回流條件下以2小時進行胺基之順丁烯二醯亞胺化反應。靜置冷卻後,加入甲苯100份,以水100份洗滌有機層5次。加熱減壓下,藉由餾去溶劑,而獲得作為褐色固形樹脂的下述式(11)所示之順丁烯二醯亞胺化合物(M-3)117份。將所得的順丁烯二醯亞胺化合物的GPC圖表示於圖8。數目平均分子量(Mn)為1353、重量平均分子量(Mw)為1562。 In a flask equipped with a thermometer, cooling tube, stirrer, and Dean Stark apparatus, add 50 parts of toluene, 53.9 parts of maleic anhydride, and 2 parts of methanesulfonic acid, and drip for 1 hour while maintaining the reflux state. Add the toluene and N-methylpyrrolidone (NMP) solution of A-1 (A-1: 100 parts, toluene: 75 parts, NMP 25 parts). The maleic acid imidization reaction of the amine group was carried out under reflux conditions for 2 hours. After leaving to cool, 100 parts of toluene was added, and the organic layer was washed 5 times with 100 parts of water. The solvent was distilled off under heating and reduced pressure to obtain 117 parts of a maleimide compound (M-3) represented by the following formula (11) as a brown solid resin. The GPC chart of the obtained maleimide compound is shown in FIG. 8 . The number average molecular weight (Mn) is 1353, and the weight average molecular weight (Mw) is 1562.
〔實施例3至6、比較例1〕 [Examples 3 to 6, Comparative Example 1]
將實施例1至2、合成例2所得的各順丁烯二醯亞胺化合物(M-1、M-2、M-3)及熱自由基起始劑DCP(過氧化二異丙苯,東京化成公司製)各別以表1、表2所示之比率混合後,一邊以鏡面銅箔(T4X:福田金屬銅箔公司製)夾持,一邊進行真空壓成型,在220℃硬化2小時。此時,就間隔物而言,係使用將厚度250μm之緩衝紙之中央挖空縱橫150mm者。在評估時,因應需要而使用雷射裁剪機切出所期望的尺寸的試驗片並實施評估。將評估結果示於表1、表2。 Each of the maleimide compounds (M-1, M-2, M-3) obtained in Examples 1 to 2 and Synthesis Example 2 and the thermal radical initiator DCP (dicumyl peroxide, (manufactured by Tokyo Chemical Industry Co., Ltd.) are mixed at the ratios shown in Table 1 and Table 2 respectively, and then vacuum press-molded while clamped with mirror copper foil (T4X: manufactured by Fukuda Metal Copper Foil Co., Ltd.), and cured at 220°C for 2 hours. . At this time, as a spacer, a buffer paper with a thickness of 250 μm was used in which the center was hollowed out by 150 mm in length and width. During the evaluation, if necessary, use a laser cutting machine to cut test pieces of the desired size and perform evaluation. The evaluation results are shown in Table 1 and Table 2.
<介電常數試驗、介電正切試驗> <Dielectric constant test, dielectric tangent test>
使用ATE股份有限公司製的10GHz空腔共振器,藉由空腔共振器擾動法進行測試。試樣尺寸係設為寬1.7mm×長100mm,以厚度0.3mm進行試驗。 Using a 10GHz cavity resonator manufactured by ATE Co., Ltd., the test was conducted by the cavity resonator perturbation method. The sample size was set to 1.7mm in width x 100mm in length, and the test was conducted with a thickness of 0.3mm.
[表1]
<耐熱性:示差掃描熱量測定(DSC)> <Heat resistance: Differential scanning calorimetry (DSC)>
使用示差掃描熱析儀測定實施例5及6之試料的玻璃轉移點Tg。 The glass transition point Tg of the samples of Examples 5 and 6 was measured using a differential scanning thermal analyzer.
示差掃描熱析儀:DSC6220(SII Nanotechnology公司製) Differential scanning thermal analyzer: DSC6220 (manufactured by SII Nanotechnology Co., Ltd.)
測定溫度範圍:30至330℃ Measuring temperature range: 30 to 330℃
升溫速度:10℃/分鐘 Heating rate: 10℃/min
環境氣體:氮(30mL/min) Ambient gas: nitrogen (30mL/min)
試料量:5mg Sample volume: 5mg
Tg:將DSC圖表之反曲點設為Tg。 Tg: Set the inflection point of the DSC chart to Tg.
[表2]
依據表1、表2之結果,確認到本發明之硬化性樹脂組成物介電特性及耐熱性優異。 Based on the results in Table 1 and Table 2, it was confirmed that the curable resin composition of the present invention has excellent dielectric properties and heat resistance.
本專利申請案係基於在2022年3月28日申請的日本專利申請2022-052578號而主張優先權。 This patent application claims priority based on Japanese Patent Application No. 2022-052578 filed on March 28, 2022.
[產業利用性] [Industrial Applicability]
含有本發明之順丁烯二醯亞胺化合物之硬化性樹脂組成物及由此硬化而得的硬化物,係適宜使用於半導體密封材、印刷配線基板、組裝積層板等電氣電子零件。 The curable resin composition containing the maleimide compound of the present invention and the cured product obtained by curing thereof are suitable for use in electrical and electronic components such as semiconductor sealing materials, printed wiring boards, and assembly laminates.
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