CN114573946B - 无卤低介电环氧树脂组合物、积层板以及印刷电路板 - Google Patents
无卤低介电环氧树脂组合物、积层板以及印刷电路板 Download PDFInfo
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- CN114573946B CN114573946B CN202011385802.0A CN202011385802A CN114573946B CN 114573946 B CN114573946 B CN 114573946B CN 202011385802 A CN202011385802 A CN 202011385802A CN 114573946 B CN114573946 B CN 114573946B
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 64
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 229920005989 resin Polymers 0.000 claims abstract description 41
- 239000011347 resin Substances 0.000 claims abstract description 41
- 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 claims abstract description 12
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003063 flame retardant Substances 0.000 claims abstract description 11
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 11
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 10
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims abstract description 10
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 6
- 239000005011 phenolic resin Substances 0.000 claims abstract description 6
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims description 26
- 239000000758 substrate Substances 0.000 claims description 23
- -1 phosphazene compound Chemical class 0.000 claims description 17
- 239000011258 core-shell material Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 229920003986 novolac Polymers 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 10
- 239000012745 toughening agent Substances 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 9
- 239000004744 fabric Substances 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 239000011256 inorganic filler Substances 0.000 claims description 9
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002978 peroxides Chemical class 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 6
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 6
- 229930185605 Bisphenol Natural products 0.000 claims description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 5
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 4
- 239000004114 Ammonium polyphosphate Substances 0.000 claims description 4
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 4
- 229920000388 Polyphosphate Polymers 0.000 claims description 4
- PZBFGYYEXUXCOF-UHFFFAOYSA-N TCEP Chemical compound OC(=O)CCP(CCC(O)=O)CCC(O)=O PZBFGYYEXUXCOF-UHFFFAOYSA-N 0.000 claims description 4
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims description 4
- 229920001276 ammonium polyphosphate Polymers 0.000 claims description 4
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011888 foil Substances 0.000 claims description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
- VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 claims description 4
- 239000001205 polyphosphate Substances 0.000 claims description 4
- 235000011176 polyphosphates Nutrition 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 4
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 claims description 3
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical group C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 claims description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 3
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052582 BN Inorganic materials 0.000 claims description 3
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 claims description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 claims description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- FCEOGYWNOSBEPV-FDGPNNRMSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical group [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FCEOGYWNOSBEPV-FDGPNNRMSA-N 0.000 claims description 3
- JUPWRUDTZGBNEX-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O JUPWRUDTZGBNEX-UHFFFAOYSA-N 0.000 claims description 3
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 3
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- VVYDVQWJZWRVPE-UHFFFAOYSA-L dimethyltin(2+);diiodide Chemical compound C[Sn](C)(I)I VVYDVQWJZWRVPE-UHFFFAOYSA-L 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 229910021389 graphene Inorganic materials 0.000 claims description 3
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 claims description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 3
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims description 3
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 3
- 239000001095 magnesium carbonate Substances 0.000 claims description 3
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 3
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- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 claims description 3
- POPVULPQMGGUMJ-UHFFFAOYSA-N octasilsesquioxane cage Chemical compound O1[SiH](O[SiH](O2)O[SiH](O3)O4)O[SiH]4O[SiH]4O[SiH]1O[SiH]2O[SiH]3O4 POPVULPQMGGUMJ-UHFFFAOYSA-N 0.000 claims description 3
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
- PRCNQQRRDGMPKS-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O.CC(=O)CC(C)=O PRCNQQRRDGMPKS-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 3
- BQPNUOYXSVUVMY-UHFFFAOYSA-N [4-[2-(4-diphenoxyphosphoryloxyphenyl)propan-2-yl]phenyl] diphenyl phosphate Chemical compound C=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 BQPNUOYXSVUVMY-UHFFFAOYSA-N 0.000 claims description 2
- GCKAMTHMSCXVIL-UHFFFAOYSA-N bis(2,3-dimethylphenyl) (3-hydroxyphenyl) phosphate Chemical compound P(=O)(OC1=C(C(=CC=C1)C)C)(OC1=C(C(=CC=C1)C)C)OC1=CC(O)=CC=C1 GCKAMTHMSCXVIL-UHFFFAOYSA-N 0.000 claims description 2
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 claims description 2
- VNNDVNZCGCCIPA-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;manganese Chemical compound [Mn].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O VNNDVNZCGCCIPA-FDGPNNRMSA-N 0.000 claims 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 abstract description 5
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 abstract description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 35
- 239000011889 copper foil Substances 0.000 description 32
- 238000012360 testing method Methods 0.000 description 20
- 229920001955 polyphenylene ether Polymers 0.000 description 13
- 230000009477 glass transition Effects 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
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- 238000004513 sizing Methods 0.000 description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
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- 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
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- 150000002148 esters Chemical class 0.000 description 3
- 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 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
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- GKGXKPRVOZNVPQ-UHFFFAOYSA-N diisocyanatomethylcyclohexane Chemical compound O=C=NC(N=C=O)C1CCCCC1 GKGXKPRVOZNVPQ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- JFOJYGMDZRCSPA-UHFFFAOYSA-J octadecanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JFOJYGMDZRCSPA-UHFFFAOYSA-J 0.000 description 1
- NWAHZAIDMVNENC-UHFFFAOYSA-N octahydro-1h-4,7-methanoinden-5-yl methacrylate Chemical compound C12CCCC2C2CC(OC(=O)C(=C)C)C1C2 NWAHZAIDMVNENC-UHFFFAOYSA-N 0.000 description 1
- ZWCNRMDCQDJIRL-UHFFFAOYSA-N octavinyloctasilasesquioxane Chemical compound O1[Si](O[Si](O2)(O[Si](O3)(O4)C=C)C=C)(C=C)O[Si]4(C=C)O[Si]4(C=C)O[Si]1(C=C)O[Si]2(C=C)O[Si]3(C=C)O4 ZWCNRMDCQDJIRL-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/092—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising epoxy resins
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/04—Impregnation, embedding, or binder material
- B32B2260/046—Synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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Abstract
本发明公开一种无卤低介电环氧树脂组合物、积层板以及印刷电路板。本发明的无卤低介电环氧树脂组合物包括：(a)5至15重量份的二环戊二烯型环氧树脂；(b)25至35重量份的甲酚醛环氧树脂；(c)55至65重量份的马来酰亚胺树脂；(d)20至30重量份的DOPO‑双酚酚醛树脂硬化剂；(e)65至75重量份的氰酸酯树脂；(f)5至15重量份的交联剂；以及(g)35至45重量份的非DOPO阻燃剂。本发明的无卤低介电环氧树脂组合物通过特定的组成份及比例，可提供不含聚苯醚的环氧树脂组合物，且其具有低介电指数，同时提升板材韧性及耐热性。
Description
技术领域
本发明涉及一种低介电组合物、积层板以及印刷电路板，特别是涉及一种不包括聚苯醚的无卤低介电环氧树脂组合物、积层板以及印刷电路板。
背景技术
印刷电路板技术中，主要是包括环氧树脂与硬化剂的热固性树脂组合物，并与补强材料加热结合形成半固化胶片(prepreg)，再于高温高压将其与上、下两片铜箔压合而成铜箔积层板(或称铜箔基板)。
聚苯醚(PPE)树脂因具有良好的机械特性与优异介电性能，例如介电常数(Dk)及介电损耗(Df)，成为高频印刷电路板的基板首选的树脂材料。然而，聚苯醚是一种热塑性树脂，市面可购得的聚苯醚多为大分子量(数均平均分子量>20,000)聚苯醚树脂，与溶剂的溶解性不佳，且与环氧树脂相容性差，单纯使用聚苯醚树脂制作的铜箔基板玻璃转化温度(Tg)不够高。
而小分子量聚苯醚树脂，虽可改善与溶剂的溶解度，但聚苯醚分子结构的极性基特性，会造成介电损耗升高。此外，现有技术于聚苯醚树脂中加入其他材料，虽然可提升铜箔基板的玻璃转化温度、改善介电损耗，但却同时会造成其他问题，如硬化后交联度不足、耐热性变差、压合后的基板容易产生树枝状条纹的缺点，而特别是基板具有树枝状条纹会使铜箔基板后续制作的电路板的信赖性变差及良率大幅降低。
此外，现有技术用于取代聚苯醚树脂的环氧树脂配方成品的介电常数值较差，无法满足新一代高频低介电的电路板所要求的特性。因此，本发明期望开发通过特定环氧树酯配方取代聚苯醚树脂的无卤低介电环氧树脂组合物，进一步开发出具有优异介电性能以及符合印刷电路板其他特性需求，诸如高玻璃转化温度(Tg)、低热膨胀系数、低吸水率特性的材料，并将其应用于高频印刷电路板的制造，乃是现阶段印刷电路板材料供货商亟欲解决的问题。
发明内容
本发明所要解决的技术问题在于，针对现有技术的不足提供一种无卤低介电环氧树脂组合物、积层板以及印刷电路板。
为了解决上述的技术问题，本发明所采用的其中一技术方案是提供一种无卤低介电环氧树脂组合物，其特征在于，所述无卤低介电环氧树脂组合物包括：
5至15重量份的二环戊二烯型环氧树脂；
25至35重量份的甲酚醛环氧树脂；
55至65重量份的马来酰亚胺树脂；
20至30重量份的DOPO-双酚酚醛树脂硬化剂；
65至75重量份的氰酸酯树脂；
5至15重量份的交联剂；
35至45重量份的非DOPO阻燃剂；以及
1至5重量份的一增韧剂，且所述增韧剂是一核壳聚合物，包括一中间层含有30至100重量％的多官能性单体及0至70重量％的乙烯系单体，且所述核壳聚合物的壳部包括环氧基单体。
更进一步地，所述DOPO-双酚酚醛树脂是选自DOPO-双酚A线型酚醛树脂(DOPO-BPAN)、DOPO-双酚F线型酚醛树脂(DOPO-BPSN)以及DOPO-双酚S线型酚醛树脂(DOPO-BPSN)所组成的群组。
更进一步地，所述交联剂是选自三烯丙基异氰酸酯、三烯丙基氰酸酯、八乙烯基八硅倍半氧烷、三乙烯基胺所组成的群组。
更进一步地，所述非DOPO阻燃剂是选自间苯二酚双二甲苯基磷酸盐、聚磷酸三聚氰胺、三(2-羧乙基)膦、三甲基磷酸盐、三(异丙基氯)磷酸盐、二甲基-甲基磷酸盐、双酚联苯磷酸盐、聚磷酸铵、对苯二酚-双-(联苯基磷酸盐)、双酚A-双-(联苯基磷酸盐)以及磷腈化合物所组成的群组。
更进一步地，一硬化促进剂，所述硬化促进剂是选自磷系硬化促进剂、胺系硬化促进剂、咪唑系硬化促进剂、胍系硬化促进剂、金属系硬化促进剂以及过氧化物系硬化促进剂所组成的群组。
更进一步地，所述金属系硬化促进剂是选自乙酰基丙酮酸钴(II)、乙酰基丙酮酸钴(III)等的有机钴错合物、乙酰基丙酮酸铜(II)等的有机铜错合物、乙酰基丙酮酸锌(II)等的有机锌错合物、乙酰基丙酮酸铁(III)等的有机铁错合物、乙酰基丙酮酸镍(II)等的有机镍错合物以及乙酰基丙酮酸锰(II)所组成的群组；所述过氧化物系硬化促进剂是选自环己酮过氧化物、过氧化苯甲酸叔丁基酯、甲基乙基酮过氧化物、过氧化二异丙苯、叔丁基过氧化异丙苯、二叔丁基过氧化物、过氧化氢二异丙苯、氢过氧化异丙苯以及叔丁基过氧化氢所组成的群组。
更进一步地，所述无卤低介电环氧树脂组合物进一步包括：一无机填料，所述无机填料是选自二氧化硅、氧化铝、氢氧化铝、氧化镁、氢氧化镁、碳酸钙、氮化铝、氮化硼、碳化铝硅、碳化硅、二氧化钛、氧化锌、氧化锆、硫酸钡、碳酸镁、碳酸钡、云母、滑石以及石墨烯所组成的群组。
更进一步地，所述多官能性单体是选自二乙烯基苯、丁二醇二(甲基)丙烯酸酯、(异)三聚氰酸三烯丙酯、(甲基)丙烯酸烯丙酯、伊康酸二烯丙酯以及邻苯二甲酸二烯丙酯所组成的群组；所述乙烯系单体是烷基残基的碳数为1至10的(甲基)丙烯酸酯。
为了解决上述的技术问题，本发明所采用的另外一技术方案是提供一种积层板，其包括：一树脂基板，其包括多个半固化胶片，且每一所述半固化胶片由一玻璃纤维布经由涂覆本发明的无卤低介电环氧树脂组合物所制成；以及一金属箔层，其设置于所述树脂基板的至少一表面上。
为了解决上述的技术问题，本发明所采用的另外再一技术方案是，提供一种印刷电路板，其包括如本发明的积层板。
本发明的其中一有益效果在于，本发明所提供的无卤低介电环氧树脂组合物、积层板以及印刷电路板，其能通过通过特定的组成份及比例，可提供不含聚苯醚的低介电无卤组合物，同时提升板材韧性及耐热性，并降低成本。再者，此组合物可制作成半固化胶片或树脂膜，进而达到可应用于铜箔基板及印刷电路板之目的，就产业上的可利用性而言，利用本发明所衍生的产品，当可充分满足目前市场的需求。
为使能更进一步了解本发明的特征及技术内容，请参阅以下有关本发明的详细说明，然而所提供的说明内容仅用于提供参考与说明，并非用来对本发明加以限制。
具体实施方式
以下是通过特定的具体实例。本发明的一具体实施例提供一种无卤低介电环氧树脂组合物，其包括：
5至15重量份的二环戊二烯型环氧树脂；
25至35重量份的甲酚醛环氧树脂；
55至65重量份的马来酰亚胺树脂；
20至30重量份的DOPO-双酚酚醛树脂硬化剂；
65至75重量份的氰酸酯树脂；
5至15重量份的交联剂；
35至45重量份的非DOPO阻燃剂；以及
1至5重量份的一增韧剂，且所述增韧剂是一核壳聚合物，包括一中间层含有30至100重量％的多官能性单体及0至70重量％的乙烯系单体，且所述核壳聚合物的壳部包括环氧基单体。
优选地，本发明通过使用环氧树脂取代现有技术所使用的聚苯醚树脂，而预期达到现有技术使用聚苯醚才可获得的低介电指数，因此，本发明使用了二环戊二烯型环氧树脂(DCPD)以及甲酚酚醛型环氧树脂(Cresol novolac epoxy)的组合，不添加聚苯醚树脂。更具体来说，二环戊二烯型(DCPD)环氧树脂可以有效降低介电常数(Dk)数值，降低Dk至4.1。甲酚酚醛型环氧树脂可提高玻璃转化温度(Tg)，更降低电性。
本发明的双马来酰亚胺树脂并未特别的限制，主要是分子中含有两个马来酰亚胺基团的化合物，也可以使用双马来酰亚胺化合物的预聚物，或双马来酰亚胺化合物与胺化合物的预聚物。优选地，双马来酰亚胺是选自双(4-马来酰亚胺基苯基)甲烷、2,2-双(4-(4-马来酰亚胺基苯氧基)-苯基)丙烷、双(3,5-二甲基-4-马来酰亚胺基苯基)甲烷、双(3-乙基-5-甲基-4-马来酰亚胺基苯基)甲烷和双(3,5-二乙基-4-马来酰亚胺基苯基)甲烷所组成的群组。
本发明的DOPO-双酚酚醛树脂硬化剂是选自DOPO-双酚A线型酚醛树脂(DOPO-BPAN)、DOPO-双酚F线型酚醛树脂(DOPO-BPSN)以及DOPO-双酚S线型酚醛树脂(DOPO-BPSN)所组成的群组。更佳地，本发明的DOPO-双酚酚醛树脂硬化剂是DOPO-双酚A线型酚醛树脂(DOPO-BPAN)。
详细来说，9,10-二氢-9-氧杂-10-磷菲-10-氧化物(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide，DOPO)改质硬化剂主要是做为与环氧树脂结合的硬化剂使用，改质硬化剂除了可提供良好的热稳定性和低介电性外，更可提升阻燃的功效。
本发明所使用的氰酸酯树脂并无特别限定，氰酸酯树脂可增加树脂结构中的反应官能团，提高玻璃转化温度(Tg)，更降低电性。举例而言，氰酸酯树脂可以是多官能脂肪族系异氰酸酯化合物、多官能脂环族系异氰酸酯、多官能芳香族系异氰酸酯化合物，如：三亚甲基二异氰酸酯、四亚甲基二异氰酸酯、六亚甲基二异氰酸酯、五亚甲基二异氰酸酯、1,2-伸丙基二异氰酸酯、1,3-伸丁基二异氰酸酯、十二亚甲基二异氰酸酯、2,4,4-三甲基六亚甲基二异氰酸酯等、1,3-环戊烯二异氰酸酯、1,3-环己烷二异氰酸酯、1,4-环己烷二异氰酸酯、异佛尔酮二异氰酸酯、氢化二苯基甲烷二异氰酸酯、氢化苯二亚甲基二异氰酸酯、氢化甲苯二异氰酸酯、氢化四甲基苯二亚甲基二异氰酸酯、伸苯基二异氰酸酯、2,4-甲苯二异氰酸酯、2,6-甲苯二异氰酸酯、2,2’－二苯基甲烷二异氰酸酯、4,4’－二苯基甲烷二异氰酸酯、4,4’－甲苯胺二异氰酸酯、4,4’－二苯基醚二异氰酸酯、4,4’－二苯基二异氰酸酯、1,5-萘二异氰酸酯、苯二亚甲基二异氰酸酯，非芳香族二异氰酸酯，像是六亚甲基二异氰酸酯、4,4’－二环己基甲烷二异氰酸酯、2,4’－二环己基甲烷二异氰酸酯、2,2,4－三甲基六亚甲基二异氰酸酯、二异氰酸异佛尔酮、离胺酸二异氰酸酯；或是其他非芳香族二异氰酸酯，像是环己基甲烷二异氰酸酯、1,6－六亚甲基二异氰酸酯等。特别是异氰酸酯树脂(isocyanate－type)如:芳香族二异氰酸酯(aromatic isocyanates)，像是4,4’－二苯基甲烷二异氰酸酯、三氯乙烯二异氰酸酯、二甲苯二异氰酸酯、4,4’－二苯醚二异氰酸酯、4,4’－[2,2－双(4－苯氧基苯基丙酮)二异氰酸酯]。
本发明的交联剂是选自三烯丙基异氰酸酯(Triallyl isocyanurate，TAIC)、三烯丙基氰酸酯(Triallyl cyanurate，TAC)、八乙烯基八硅倍半氧烷(Octavinyloctasilasesquioxane)、三乙烯基胺(trivinyl-amine)所组成的群组。优选地，交联剂为三烯丙基异氰酸酯。交联剂用以协同硬化剂，提供交联反应，若交联剂比例过高，则会降低树脂组合物交联后的导热性质(比如降低热传导系数K值)。若交联剂的比例过低，则会导致树脂组合物交联后的热性值不佳(例如玻璃转移温度Tg降低)。优选地，交联剂可以是三烯丙基异氰酸酯。
本发明所定义的非DOPO阻燃剂，意即不含9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)衍生物。详细而言，DOPO结构内的P-O-C键结容易水解为P-OH，会使材料介电常数及介电损耗上升，故选用非DOPO阻燃剂可避免提升材料的Dk以及DF，其中，Dk即为介电常数(Dielectric Constant，εr)，DF为介电损耗。
更详细来说，非DOPO阻燃剂是选自间苯二酚双二甲苯基磷酸盐(resorcinoldixylenylphosphate，RDXP(如PX-200))、聚磷酸三聚氰胺(melamine polyphosphate)、三(2-羧乙基)膦(tri(2-carboxyethyl)phosphine，TCEP)、三甲基磷酸盐(trimethylphosphate，TMP)、三(异丙基氯)磷酸盐、二甲基-甲基磷酸盐(dimethyl methylphosphonate，DMMP)、双酚联苯磷酸盐(bisphenol diphenyl phosphate)、聚磷酸铵(ammonium polyphosphate)、对苯二酚-双-(联苯基磷酸盐)(hydroquinone bis-(diphenyl phosphate))、双酚A-双-(联苯基磷酸盐)(bisphenol A bis-(diphenylphosphate))以及磷腈化合物(Phosphazene，如SPB-100、SPH-100、SPV-100等市售产品)所组成的群组。优选地，可以是20至30重量份的间苯二酚双二甲苯基磷酸盐搭配5至15重量份的磷腈化合物(如SPB-100)。
优选地，硬化促进剂可使氰酸酯开环反应，是选自磷系硬化促进剂、胺系硬化促进剂、咪唑系硬化促进剂、胍系硬化促进剂、金属系硬化促进剂、过氧化物系硬化促进剂。较佳是金属系硬化促进剂与过氧化物系硬化促进剂混合。更佳地，可以是基于环氧树脂100重量份1重量份的金属系硬化促进剂与2重量份过氧化物系硬化促进剂。
更具体来说，金属系硬化促进剂，可举出例如钴、铜、锌、铁、镍、锰、锡等的金属的有机金属错合物或有机金属盐。作为有机金属错合物的具体例，可举出乙酰基丙酮酸钴(II)、乙酰基丙酮酸钴(III)等的有机钴错合物、乙酰基丙酮酸铜(II)等的有机铜错合物、乙酰基丙酮酸锌(II)等的有机锌错合物、乙酰基丙酮酸铁(III)等的有机铁错合物、乙酰基丙酮酸镍(II)等的有机镍错合物、乙酰基丙酮酸锰(II)等的有机锰错合物。作为有机金属盐，可举出例如辛酸锌、辛酸锡、环烷酸锌、环烷酸钴、硬脂酸锡、硬脂酸锌。
过氧化物系硬化促进剂，可举出例如环己酮过氧化物、过氧化苯甲酸叔丁基酯、甲基乙基酮过氧化物、过氧化二异丙苯、叔丁基过氧化异丙苯、二叔丁基过氧化物、过氧化氢二异丙苯、氢过氧化异丙苯、叔丁基过氧化氢。
另一方面，无机填料可增加无卤低介电环氧树脂组合物的热传导性，改良其热膨胀性以及机械强度，优选地，无机填料是均匀分布于无卤低介电环氧树脂组合物中。较佳地，无机填料可经由硅烷偶合剂预先进行表面处理。优选地，无机填料可为球型、片状、粒状、柱状、板状、针状或不规则状的无机填料。优选地，无机填料选自二氧化硅(如熔融态、非熔融态、多孔质或中空型的二氧化硅)、氧化铝、氢氧化铝、氧化镁、氢氧化镁、碳酸钙、氮化铝、氮化硼、碳化铝硅、碳化硅、二氧化钛、氧化锌、氧化锆、硫酸钡、碳酸镁、碳酸钡、云母、滑石、石墨烯所组成的群组。优选地，无机填料的添加量可以是以100重量份的环氧树脂为基准的250至300重量份。优选地，可使用Sibelco公司制的Megasil525 ARI，可有效提升热传导性、机械强度及降低热膨胀性。
此外，本发明的无卤低介电环氧树脂组合物更进一步包括适量的溶剂，举例而言，酮类、酯类、醚类、醇类等，更具体而言，本发明的溶剂是选自丙酮、丁酮、丙二醇甲醚、丙二醇甲醚醋酸酯、二甲基乙酰胺以及环己酮所组成的群组。举例来说，溶剂可以选自50至60重量份的丁酮(MEK)以及30至40重量份的Toluene(甲苯)的组合或其他溶剂等的组合。
更进一步地，本发明的无卤低介电环氧树脂组合物视需求进一步包括增韧剂，如核壳聚合物，在不影响玻璃转化温度(Tg)的同时，可用以提高板材韧性，也提升板材的耐热性能。优选地，增韧剂可选自环氧树脂型增韧剂，如KANEKA的MX系列产品，添加量可以是以100重量份的环氧树脂为基准的1～5重量份。具体来说，上述核壳聚合物的体积平均粒径为0.01至1μm，较佳为0.1至0.5μm，且上述核壳聚合物的核部的玻璃转化温度(Tg)未达0℃，且上述核壳聚合物的壳部的玻璃转化温度(Tg)未达20℃，更详细来说，上述核壳聚合物于核部与壳部之间含有中间层，中间层含有30至100重量％的多官能性单体及0至70重量％的乙烯系单体，较佳为50至98重量％的多官能性单体及2至50重量％的乙烯系单体，且上述核壳聚合物的壳部包括环氧基单体，通过核壳聚合物的环氧基单体与环氧树脂环氧基的结合，及核壳聚合物良好的分散性可以更加提升本发明组合物的耐热性能。
作为多官能性单体，如：二乙烯基苯、丁二醇二(甲基)丙烯酸酯、(异)三聚氰酸三烯丙酯、(甲基)丙烯酸烯丙酯、伊康酸二烯丙酯、邻苯二甲酸二烯丙酯等。
作为乙烯系单体，例如较佳为烷基残基的碳数为1～10的(甲基)丙烯酸酯。作为可与甲基丙烯酸甲酯共聚合的其他乙烯系单体，具体而言，可列举：甲基丙烯酸乙酯、甲基丙烯酸丁酯、甲基丙烯酸环己酯、甲基丙烯酸苄酯、甲基丙烯酸缩水甘油酯、甲基丙烯酸环氧环己基甲酯、甲基丙烯酸2-羟乙酯、甲基丙烯酸2-羟丙酯、甲基丙烯酸二环戊酯、甲基丙烯酸2,2,2-三氟乙酯、甲基丙烯酸2,2,2-三氯乙酯等甲基丙烯酸酯类；丙烯酸甲酯、丙烯酸乙酯、丙烯酸丁酯、丙烯酸2-乙基己酯、丙烯酸缩水甘油酯、丙烯酸环氧环己基甲酯、丙烯酸2-羟乙酯、丙烯酸2-羟丙酯等丙烯酸酯类；甲基丙烯酸、丙烯酸等羧酸类及其酯类；丙烯腈、甲基丙烯腈等乙烯氰(Vinylcyan)类；苯乙烯、α-甲基苯乙烯、单氯苯乙烯、二氯苯乙烯等乙烯芳烃类；顺丁烯二酸、反丁烯二酸及该等的酯等；氯乙烯、溴乙烯、氯丁二烯等卤化乙烯类；乙酸乙烯酯；乙烯、丙烯、丁烯、丁二烯、异丁烯等烯烃类：卤化烯烃类；甲基丙烯酸烯丙酯、邻苯二甲酸二烯丙酯、氰尿酸三烯丙酯、单乙二醇二甲基丙烯酸酯、四乙二醇二甲基丙烯酸酯、四乙二醇二甲基丙烯酸酯、二乙烯苯等多官能性单体。该等乙烯系单体可单独使用或并用两种以上。
作为壳部的环氧基单体，可以是具有乙烯性不饱和双键与环氧基的单体，如：烯丙基缩水甘油醚等醚系化合物；(甲基)丙烯酸缩水甘油酯、烯丙基缩水甘油醚、(甲基)丙烯酸缩水甘油基烷基酯等酯系化合物(尤其含环氧基的(甲基)丙烯酸酯)。
本发明还提供另外一技术方案是一种积层板，其包括：(a)树脂基板，其包括多个半固化胶片，且每一所述半固化胶片由一玻璃纤维布经由涂覆如本发明的无卤低介电环氧树脂组合物所制成；以及(b)金属箔层，其设置于树脂基板的至少一表面上，或可视需求使得树脂基板上下设置金属箔层。
除此之外，本发明更提供另外再一技术方案是一种印刷电路板，其包括本发明的积层板。
以下将针对本发明的无卤环氧树脂组合物以及进行多组实施例以及比较例的，以说明通过本发明特定的组成比例调配而达成最佳的积层板特性。
实施例
以下实施例E1～E4是使用本发明的无卤低介电环氧树脂组合物在一连续的过程中制造半固化胶片。通常是以玻璃纤维布作基材。卷状的玻璃纤维布连续地穿过一系列滚轮进入上胶槽，槽里装有本发明的无卤低介电环氧树脂组合物。在上胶槽里玻璃纤维布被树脂充分浸润，然后经过计量辊刮除多余的树脂，进入上胶炉烘烤一定的时间，使溶剂蒸发并使树脂固化一定程度，冷却，收卷，形成半固化胶片，然后将上述批制得的半固化胶片，取同一批的半固化胶片四张及两张18μm铜箔，依铜箔、四片半固化胶片、铜箔的顺序进行迭合，再于真空条件下经由220℃压合2小时形成铜箔基板，其中四片半固化胶片固化形成两铜箔间的绝缘层。
表1
*DCPD epoxy：长春人造树脂DNE260A75二环戊二烯型环氧树脂。
*Cresol novolac epoxy：长春人造树脂CNE-202甲酚醛环氧树脂。
*Bismaleimides：KI公司制KI-70。
*Cyanate ester：Lonza公司制BA-230S75。
*核壳聚合物：KANEKA的MX系列产品。
比较例
依据下述表2的比较例C1至C7的组份及比例在一连续的过程中制造半固化胶片。通常是以玻璃纤维布作基材。卷状的玻璃纤维布连续地穿过一系列滚轮进入上胶槽，槽里装有本发明的无卤低介电环氧树脂组合物。在上胶槽里玻璃纤维布被树脂充分浸润，然后经过计量辊刮除多余的树脂，进入上胶炉烘烤一定的时间，使溶剂蒸发并使树脂固化一定程度，冷却，收卷，形成半固化胶片，然后将上述批制得的半固化胶片，取同一批的半固化胶片四张及两张18μm铜箔，依铜箔、四片半固化胶片、铜箔的顺序进行迭合，再于真空条件下经由220℃压合2小时形成铜箔基板，其中四片半固化胶片固化形成两铜箔间的绝缘层。
表2
*HP-7200：DCPD(二环戊二烯型)型环氧树脂。
*NC-3000：日本化药公司联苯型环氧树脂。
*式1～3的马来酸酐改质聚酰亚胺树脂以及式I～III阻燃剂：参酌第TWI632190专利号及第TW109106662申请号。
物性测试
分别将上述实施例E1至E4及比较例C1至C7的铜箔积层板进行物性测试，并纪录测试结果于表3：
玻璃转化温度(Tg)：根据差示扫描量热法(DSC)，依据IPC-TM-650 2.4.25所规定的DSC方法进行测定。
铜箔积层板耐热性(T288)：也称“漂锡结果”，耐热实验是依据产业标准IPC-TM-650 2.4.24.1，将铜箔积层板浸泡于288℃锡炉至爆板所需时间。
含铜箔积层板吸湿后浸锡测试：使用含铜箔层的半固化胶片进行耐热性(T288)测试，依据产业标准IPC-TM-650 2.4.24.1，将铜箔积层板浸泡于288℃锡炉至爆板所需时间。
铜箔积层板耐热性(S/D)测试：含铜基板浸锡测试(solder dip 288℃，10秒，测耐热回数)。
铜箔积层板耐热性(PCT)测试：不含铜基板PCT吸湿后浸锡测试(pressurecooking at 121℃，1小时后，测solder dip 288℃，20秒观看有无爆板)。
铜箔与基板间拉力(peeling strength,half ounce copper foil,P/S)：依据IPC－TM－650 2.4.1检测规范进行测定。
介电常数(Dk)：依据IPC－TM－650 2.5.5检测规范进行测定，介电常数代表所制胶片的电子绝缘特性，数值越低代表电子绝缘特性越好。
介电损耗(Df)：依据IPC－TM－650 2.5.5检测规范进行测定，介电损耗表示物质在一定温度下吸收某一频率的微波的能力，通常在通讯产品的规范里，介电损耗数值需越低越好。
耐燃性(flaming test，UL94)：依据UL94垂直燃烧法测定，其以塑料材料标准试片经火焰燃烧后的自燃时间、自燃速度、掉落的颗粒状态来订定塑料材料的耐燃等级。而依耐燃等级优劣，依次是HB、V-2、V-1、V-0、最高为5V等级。而UL 94测试方法是指塑料材料以垂直方式在火焰上燃烧。以每十秒为一测试周期，其步骤如下：步骤一：将试片放进火焰中十秒再移开，测定移开之后该试片继续燃烧时间(T1)；步骤二：当试片火焰熄灭后，再放进火焰中十秒再移开，再测定移开之后该试片继续燃烧时间(T2)；步骤三：重复数次实验并取其平均值；步骤四：计算T1+T2的总合。而UL 94V-0等级的要求是为在试片单一燃烧时间T1的平均及T2的平均皆不得超过10秒，且其T1与T2的总合不得超过50秒方符合UL 94V-0要求。
表3
[实施例的有益效果]
本发明的其中一有益效果在于，本发明所提供的无卤低介电环氧树脂组合物、积层板以及印刷电路板，其能通过通过特定的组成份及比例，可提供不含聚苯醚的低介电无卤组合物，同时提升板材韧性及耐热性，并降低成本。再者，此组合物可制作成半固化胶片或树脂膜，进而达到可应用于铜箔基板及印刷电路板之目的，就产业上的可利用性而言，利用本发明所衍生的产品，当可充分满足目前市场的需求。
更进一步来说，本发明所提供的无卤低介电环氧树脂组合物所制得的铜箔积层板具有自低于4的介电强度(Dk)以及在10GHz下约0.005的介电损耗(Df)，且本发明的无卤低介电环氧树脂组合物增加了特殊的核壳聚合物增韧剂，有效提升含铜箔积层板吸湿后浸锡测试(T288)大于60分钟以及铜箔积层板耐热性(S/D)大于60秒，在不影响玻璃转化温度(Tg)的同时，可用以提高板材韧性，也提升板材的耐热性能，明显相较于现有技术有较佳的耐热效果。
以上所公开的内容仅为本发明的优选可行实施例，并非因此局限本发明的权利要求书的保护范围，所以凡是运用本发明说明书内容所做的等效技术变化，均包含于本发明的权利要求书的保护范围内。
Claims (10)
1.一种无卤低介电环氧树脂组合物，其特征在于，所述无卤低介电环氧树脂组合物包括：
(a)5至15重量份的二环戊二烯型环氧树脂；
(b)25至35重量份的甲酚醛环氧树脂；
(c)55至65重量份的双马来酰亚胺树脂；
(d)20至30重量份的DOPO-双酚酚醛树脂硬化剂；
(e)65至75重量份的氰酸酯树脂；
(f)5至15重量份的交联剂；
(g)35至45重量份的非DOPO阻燃剂；以及
(h)1至5重量份的一增韧剂，且所述增韧剂是一核壳聚合物，包括一中间层含有30至100重量％的多官能性单体及0至70重量％的乙烯系单体，且所述核壳聚合物的壳部包括环氧基单体。
2.根据权利要求1所述的无卤低介电环氧树脂组合物，其特征在于，所述DOPO-双酚酚醛树脂是选自DOPO-双酚A线型酚醛树脂、DOPO-双酚F线型酚醛树脂以及DOPO-双酚S线型酚醛树脂所组成的群组。
3.根据权利要求1所述的无卤低介电环氧树脂组合物，其特征在于，所述交联剂是选自三烯丙基异氰酸酯、三烯丙基氰酸酯、八乙烯基八硅倍半氧烷、三乙烯基胺所组成的群组。
4.根据权利要求1所述的无卤低介电环氧树脂组合物，其特征在于，所述非DOPO阻燃剂是选自间苯二酚双二甲苯基磷酸酯、聚磷酸三聚氰胺、三(2-羧乙基)膦、磷酸三甲酯、三(异丙基氯)磷酸酯、甲基膦酸二甲酯、双酚二苯磷酸酯、聚磷酸铵、对苯二酚双(磷酸二苯酯)、双酚A双(二苯基磷酸酯)以及磷腈化合物所组成的群组。
5.根据权利要求1所述的无卤低介电环氧树脂组合物，其特征在于，所述无卤低介电环氧树脂组合物进一步包括：一硬化促进剂，所述硬化促进剂是选自磷系硬化促进剂、胺系硬化促进剂、咪唑系硬化促进剂、胍系硬化促进剂、金属系硬化促进剂以及过氧化物系硬化促进剂所组成的群组。
6.根据权利要求5所述的无卤低介电环氧树脂组合物，其特征在于，所述金属系硬化促进剂是选自乙酰基丙酮酸钴(II)、乙酰基丙酮酸钴(III)的有机钴错合物、乙酰基丙酮酸铜(II)的有机铜错合物、乙酰基丙酮酸锌(II)的有机锌错合物、乙酰基丙酮酸铁(III)的有机铁错合物、乙酰基丙酮酸镍(II)的有机镍错合物以及乙酰基丙酮酸锰(II)所组成的群组；所述过氧化物系硬化促进剂是选自环己酮过氧化物、过氧化苯甲酸叔丁基酯、甲基乙基酮过氧化物、过氧化二异丙苯、叔丁基过氧化异丙苯、二叔丁基过氧化物、过氧化氢二异丙苯、氢过氧化异丙苯以及叔丁基过氧化氢所组成的群组。
7.根据权利要求1所述的无卤低介电环氧树脂组合物，其特征在于，所述无卤低介电环氧树脂组合物进一步包括：一无机填料，所述无机填料是选自二氧化硅、氧化铝、氢氧化铝、氧化镁、氢氧化镁、碳酸钙、氮化铝、氮化硼、碳化铝硅、碳化硅、二氧化钛、氧化锌、氧化锆、硫酸钡、碳酸镁、碳酸钡、云母、滑石以及石墨烯所组成的群组。
8.根据权利要求1所述的无卤低介电环氧树脂组合物，其特征在于，所述多官能性单体是选自二乙烯基苯、丁二醇二(甲基)丙烯酸酯、(异)三聚氰酸三烯丙酯、(甲基)丙烯酸烯丙酯、伊康酸二烯丙酯以及邻苯二甲酸二烯丙酯所组成的群组；所述乙烯系单体是烷基残基的碳数为1至10的(甲基)丙烯酸酯。
9.一种积层板，其特征在于，所述积层板包括：
一树脂基板，其包括多个半固化胶片，且每一所述半固化胶片由一玻璃纤维布经由涂覆如权利要求1所述的无卤低介电环氧树脂组合物所制成；以及
一金属箔层，其设置于所述树脂基板的至少一表面上。
10.一种印刷电路板，其特征在于，所述印刷电路板包括如权利要求9所述的积层板。
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