US20130075136A1 - Resin composition and prepreg, laminate and circuit board thereof - Google Patents
Resin composition and prepreg, laminate and circuit board thereof Download PDFInfo
- Publication number
- US20130075136A1 US20130075136A1 US13/239,914 US201113239914A US2013075136A1 US 20130075136 A1 US20130075136 A1 US 20130075136A1 US 201113239914 A US201113239914 A US 201113239914A US 2013075136 A1 US2013075136 A1 US 2013075136A1
- Authority
- US
- United States
- Prior art keywords
- resin
- group
- weight
- parts
- bisphenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 65
- 229920005989 resin Polymers 0.000 claims abstract description 66
- 239000011347 resin Substances 0.000 claims abstract description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 60
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 30
- 239000001301 oxygen Substances 0.000 claims abstract description 30
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 29
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 26
- 229920006380 polyphenylene oxide Polymers 0.000 claims abstract description 26
- 239000004643 cyanate ester Substances 0.000 claims abstract description 23
- XDOBJOBITOLMFI-UHFFFAOYSA-N pyrrole-2,5-dione;toluene Chemical compound CC1=CC=CC=C1.O=C1NC(=O)C=C1 XDOBJOBITOLMFI-UHFFFAOYSA-N 0.000 claims abstract description 19
- 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 21
- 239000003822 epoxy resin Substances 0.000 claims description 20
- 229920000647 polyepoxide Polymers 0.000 claims description 20
- 125000000524 functional group Chemical group 0.000 claims description 19
- -1 phenyl ethylenyl Chemical group 0.000 claims description 19
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 16
- 229920003986 novolac Polymers 0.000 claims description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 239000011256 inorganic filler Substances 0.000 claims description 10
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 239000004971 Cross linker Substances 0.000 claims description 6
- 150000001555 benzenes Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 5
- 230000004048 modification Effects 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- 239000004593 Epoxy 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
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012745 toughening agent 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
- 229930185605 Bisphenol Natural products 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 3
- 229920002857 polybutadiene Polymers 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 claims description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004114 Ammonium polyphosphate Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- 229920000388 Polyphosphate Polymers 0.000 claims description 2
- PZBFGYYEXUXCOF-UHFFFAOYSA-N TCEP Chemical compound OC(=O)CCP(CCC(O)=O)CCC(O)=O PZBFGYYEXUXCOF-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims description 2
- 229920001276 ammonium polyphosphate Polymers 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 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 2
- 125000005469 ethylenyl group Chemical group 0.000 claims description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 2
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000001205 polyphosphate Substances 0.000 claims description 2
- 235000011176 polyphosphates Nutrition 0.000 claims description 2
- 125000005470 propylenyl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 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 1
- 238000012360 testing method Methods 0.000 description 23
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 19
- 238000010521 absorption reaction Methods 0.000 description 13
- 239000011889 copper foil Substances 0.000 description 11
- 239000003063 flame retardant Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 230000008569 process Effects 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000011888 foil Substances 0.000 description 9
- 238000001723 curing Methods 0.000 description 8
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 8
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 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
- KUJCQXXXGKCKEJ-UHFFFAOYSA-N CCC.CCC.O=C1C=CC(=O)N1c1ccccc1.O=C1C=CC(=O)N1c1ccccc1.O=C1C=CC(=O)N1c1ccccc1 Chemical compound CCC.CCC.O=C1C=CC(=O)N1c1ccccc1.O=C1C=CC(=O)N1c1ccccc1.O=C1C=CC(=O)N1c1ccccc1 KUJCQXXXGKCKEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000004843 novolac epoxy resin Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- XRYYZSQXOGSWOK-UHFFFAOYSA-N C1=CC=C2OCN(C3=CC=C(CC4=CC=C(N5COC6=CC=CC=C6C5)C=C4)C=C3)CC2=C1 Chemical compound C1=CC=C2OCN(C3=CC=C(CC4=CC=C(N5COC6=CC=CC=C6C5)C=C4)C=C3)CC2=C1 XRYYZSQXOGSWOK-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000005350 fused silica glass Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000002787 reinforcement Effects 0.000 description 4
- 230000008054 signal transmission Effects 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- AHZMUXQJTGRNHT-UHFFFAOYSA-N CC(C)(C1=CC=C(OC#N)C=C1)C1=CC=C(OC#N)C=C1 Chemical compound CC(C)(C1=CC=C(OC#N)C=C1)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GAIZUCZZMVHBQO-UHFFFAOYSA-N [H]OC1=CC=C(OC2=CC=C(C3=CC=C(OC4=CC=C(O[H])C=C4)C=C3)C=C2)C=C1 Chemical compound [H]OC1=CC=C(OC2=CC=C(C3=CC=C(OC4=CC=C(O[H])C=C4)C=C3)C=C2)C=C1 GAIZUCZZMVHBQO-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000032798 delamination Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000011152 fibreglass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 2
- 208000037427 Beta-propeller protein-associated neurodegeneration Diseases 0.000 description 2
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- 239000002841 Lewis acid Substances 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- HWVKIRQMNIWOLT-UHFFFAOYSA-L cobalt(2+);octanoate Chemical compound [Co+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HWVKIRQMNIWOLT-UHFFFAOYSA-L 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 150000007527 lewis bases Chemical class 0.000 description 2
- 201000007614 neurodegeneration with brain iron accumulation 5 Diseases 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- QMAQLCVJIYANPZ-UHFFFAOYSA-N 2-propoxyethyl acetate Chemical compound CCCOCCOC(C)=O QMAQLCVJIYANPZ-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- LVGAZNUUPCRHIJ-UHFFFAOYSA-N C1=CC=C(N2COC3=CC=C(CC4=CC5=C(C=C4)OCN(C4=CC=CC=C4)C5)C=C3C2)C=C1 Chemical compound C1=CC=C(N2COC3=CC=C(CC4=CC5=C(C=C4)OCN(C4=CC=CC=C4)C5)C=C3C2)C=C1 LVGAZNUUPCRHIJ-UHFFFAOYSA-N 0.000 description 1
- VCVVODHUUPVPCA-UHFFFAOYSA-N CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.C[Y]C.C[Y]C.C[Y]C.C[Y]C.C[Y]C.C[Y]C.Oc1ccc(Cc2ccc(O)cc2)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1 Chemical compound CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.CC(C)(c1ccc(O)cc1)c1ccc(O)cc1.C[Y]C.C[Y]C.C[Y]C.C[Y]C.C[Y]C.C[Y]C.Oc1ccc(Cc2ccc(O)cc2)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1 VCVVODHUUPVPCA-UHFFFAOYSA-N 0.000 description 1
- IFSKJRQBMXSZKH-UHFFFAOYSA-N CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.C[Y]C.C[Y]C.C[Y]C.C[Y]C.C[Y]C.C[Y]C.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1 Chemical compound CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.CC.C[Y]C.C[Y]C.C[Y]C.C[Y]C.C[Y]C.C[Y]C.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.O=S(=O)(c1ccc(O)cc1)c1ccc(O)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1.Oc1ccc(Cc2ccc(O)cc2)cc1 IFSKJRQBMXSZKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- XTUAMBUGTNKAPV-UHFFFAOYSA-N N#COC1=CC=C(OC2=CC=C(C3=CC=C(OC4=CC=C(OC#N)C=C4)C=C3)C=C2)C=C1 Chemical compound N#COC1=CC=C(OC2=CC=C(C3=CC=C(OC4=CC=C(OC#N)C=C4)C=C3)C=C2)C=C1 XTUAMBUGTNKAPV-UHFFFAOYSA-N 0.000 description 1
- CWHFDTWZHFRTAB-UHFFFAOYSA-N N#COC1=CC=CC=C1 Chemical compound N#COC1=CC=CC=C1 CWHFDTWZHFRTAB-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FVHJXAUXZOAWBP-UHFFFAOYSA-N [H]OC1=C(C)C=C(OC2=CC=C(C(C)(C)C3=CC=C(OC4=CC(C)=C(O[H])C(C)=C4)C=C3)C=C2)C=C1C Chemical compound [H]OC1=C(C)C=C(OC2=CC=C(C(C)(C)C3=CC=C(OC4=CC(C)=C(O[H])C(C)=C4)C=C3)C=C2)C=C1C FVHJXAUXZOAWBP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NJXBVBPTDHBAID-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 NJXBVBPTDHBAID-UHFFFAOYSA-M 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000002156 mixing Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 150000003071 polychlorinated biphenyls Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/357—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
Definitions
- the present invention relates to a resin composition, more particularly, a thermosetting resin composition that can be used in prepreg or the insulating layer of printed circuit board.
- PCB printed circuit board
- the materials of laminate preferably has the electrical properties, thermal resistance, hygroscopic property, mechanical properties, dimensional stability, and chemical resistance needed for the process technology and market applications.
- dielectric constant and dielectric loss also called “dissipation factor”
- signal transmission speed of the laminate is inversely proportional to the square root of its dielectric constant. That is why the smaller the dielectric constant of the laminate material is better.
- lower dissipation factor means less loss in signal transmission. Thus materials with low dissipation factor provide better transmission quality.
- the primary object of the invention is to provide a resin composition, which, by using specific components at specific proportions, can offer the properties of low electric constant and low dissipation factor, and can be made into prepreg and used in PCB.
- the invention provides a resin composition, comprising: (A) 100 parts by weight of cyanate ester resin; (B) 5 to 25 parts by weight of nitrogen and oxygen containing heterocyclic compound; (C) 5 to 75 parts by weight of polyphenylene oxide (PPO) resin; and (D) 5 to 100 parts by weight of oligomer of phenylmethane maleimide.
- the aforesaid composition may be used in manufacturing prepreg, laminate and PCB.
- the resin composition of the invention can offer the properties of low electric constant and low dissipation factor, and can be made into prepreg and used in PCB.
- the component (A) cyanate ester resin in the resin composition of the invention comprises at least one selected from a group consisting of the following:
- X 1 and X 2 each independently represents at least R, Ar, SO 2 or O;
- R is selected from the group of —C(CH 3 ) 2 —, —CH(CH 3 )—, —CH 2 —, and substituted or unsubstituted dicyclopentadienyl;
- Ar is selected from the group of substituted or unsubstituted benzene, biphenyl, naphthalene, phenol novolac, bisphenol A, bisphenol A novolac, bisphenol F and bisphenol F novolac function groups;
- n is an integer greater than or equal to 1; and
- Y represents hydrogen, an aliphatic functional group or an aromatic functional group.
- the component (B) nitrogen and oxygen containing heterocyclic compound in the resin composition of the invention comprises a ring structure being simultaneously replaced by nitrogen and oxygen, and preferably comprises at least one selected from a group consisting of the following:
- X 3 represents R′ or Ar
- R′ is selected from the group of —C(CH 3 ) 3 , —CH 2 (CH 3 ), —CH 3 and substituted or unsubstituted dicyclopentadienyl
- Ar is selected from the group of substituted or unsubstituted benzene, biphenyl, naphthalene, phenol novolac, bisphenol A, bisphenol A novolac, bisphenol F and bisphenol F novolac
- X 4 and X 5 each independently represents R, Ar or —SO 2 —
- R is selected from the group of —C(CH 3 ) 2 —, —CH(CH 3 )—, —CH 2 — and substituted or unsubstituted dicyclopentadienyl
- n is an integer greater than or equal to 1
- Y is hydrogen, an aliphatic functional group or an aromatic functional group.
- the resin composition of the invention possesses the characteristics of low dielectric constant and low dissipation factor.
- the component (C) polyphenylene oxide resin in the resin composition of the invention comprises at least one selected from a group consisting of the following:
- X 6 is selected from the group of covalent bond, —SO 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )— and —CH 2 —;
- Z 1 to Z 12 each independently represents hydrogen or a methyl group;
- W represents hydroxyl, ethylenyl, phenyl ethylenyl, propylenyl, butenyl, butadienyl or epoxy function group; and n is an integer greater than or equal to 1.
- the addition of polyphenylene oxide resin to nitrogen and oxygen containing heterocyclic compound and cyanate ester resin could further lower the dielectric constant and dissipation factor of the resin composition, and its effect is more pronounced at high frequency (e.g. 1GHz to 10 GHz).
- the resin composition of the invention could also meet the UL 94 V-1 fire safety requirement.
- the component (D) oligomer of phenylmethane maleimide in the resin composition of the invention has the following structural formula:
- n and m each independently represents a positive integer greater than or equal to 1, and Y is hydrogen, an aliphatic functional group or an aromatic functional group.
- each component in the resin composition of the invention is preferably: (A) 100 parts by weight of cyanate ester resin; (B) 5 to 25 parts by weight of nitrogen and oxygen containing heterocyclic compound; (C) 5 to 75 parts by weight of polyphenylene oxide resin; and (D) 5 to 100 parts by weight of oligomer of phenylmethane maleimide, wherein if the content of nitrogen and oxygen containing heterocyclic compound is less than 5 parts by weight, its addition will not produce the effect of lower moisture absorption; if the content of nitrogen and oxygen containing heterocyclic compound is more than 25 parts by weight, the laminate made from the resin composition will show poor thermal resistance; the addition of less than 5 parts by weight of polyphenylene oxide resin will not produce the desired effect, whereas the addition of more than 75 parts by weight of polyphenylene oxide resin will result in poor (ex.
- the invention preferably and optionally includes at least one specific flame retardant compound to further improve the flame retardancy of the resin composition.
- the optional flame retardant compound includes but is not limited to phosphate compound and nitrogen-containing phosphate compound. More specifically, the flame retardant compound preferably is at least one selected from a group consisting of but not limited to bisphenol diphenyl phosphate, ammonium polyphosphate, hydroquinone bis-(diphenyl phosphate), bisphenol A bis-(diphenylphosphate), tri(2-carboxyethyl)phosphine (TCEP), tri(isopropylchloro)phosphate, trimethyl phosphate (TMP), dimethyl methyl phosphonate (DMMP), resorcinol dixylenylphosphate (RDXP) (ex.: PX-200), melamine polyphosphate, phosphazene (ex.: SPB-100), phosphazo compound, 9, 10-dihydro-9-oxa-10-phospha
- the flame retardant compound could be a DOPO compound, DOPO resin (e.g. DOPO-HQ, DOPO-PN, DOPO-BPN), or DOPO-based epoxy resin, in which DOPO-BPN could be DOPO-BPAN, DOPO-BPFN, DOPO-BPSN, or other bisphenol novolac compounds with structural formula as shown below:
- DOPO resin e.g. DOPO-HQ, DOPO-PN, DOPO-BPN
- DOPO-based epoxy resin in which DOPO-BPN could be DOPO-BPAN, DOPO-BPFN, DOPO-BPSN, or other bisphenol novolac compounds with structural formula as shown below:
- n is an integer greater than or equal to 1
- X represents DOPO functional group
- Y is covalent bond, an aliphatic functional group or an aromatic functional group
- Z is hydrogen, an aliphatic functional group or an aromatic functional group.
- X and Z could bind to any substituting group position on the benzene ring structure and each benzene ring is not limited to having one X or Z substituting group.
- a benzene ring can have two or more X substituting groups thereon, or two or more Z substituting groups thereon.
- Adding a flame retardant compound to the resin composition of the invention could increase the flame retardancy of the resin composition and cured products thereof up to UL 94 V-O fire safety level. As such, laminates and PCBs that use the resin composition would possess good flame retardancy.
- the added flame retardant compound is preferably 10 to 200 parts by weight. This preferred content markedly improves the flame retardancy of resin composition and cured products thereof without producing any adverse effect on their physical properties.
- the resin composition of the invention optionally includes at least one selected from a group consisting of epoxy resin, phenolic resin, phenol novolac resin, styrene resin, polybutadiene resin, anhydride crosslinker, and amino crosslinker, and modifications and combinations thereof.
- the epoxy resin could be bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, phenol novolac epoxy resin, bisphenol A novolac epoxy resin, o-cresol novolac epoxy resin, trifunctional epoxy resin, tetrafunctional epoxy resin, multifunctional epoxy resin, dicyclopentadiene (DCPD) epoxy resin, phosphorus-containing epoxy resin, p-xylene epoxy resin, naphthalene-based epoxy resin, benzopyran-based epoxy resin, biphenyl novolac epoxy resin, and phenol aralkyl novolac epoxy resin.
- DCPD dicyclopentadiene
- the anhydride crosslinker could be methyl tetrahydro phthalic anhydride (MTHPA), phthalic anhydride (PA), nadic methyl anhydride (NMA), or styrene maleic anhydride (SMA);
- the amino crosslinker could be polyamide resin, dicyandiamide, diamino diphenylsulfone, diamino diphenyl methane and amino triazine novolac.
- the resin composition of the invention optionally further comprises inorganic filler, surfactant, toughening agent, curing accelerator or solvent additive.
- the main purpose of adding inorganic filler is to increase the thermal conductivity of resin composition to improve its thermal expansion and mechanical strength.
- the inorganic filler is preferably evenly distributed in the resin composition.
- the main purpose of adding surfactant is to enable even distribution of inorganic fillers in the resin composition.
- the main purpose of adding toughening agent is to improve the flexibility of the resin composition.
- the main purpose of adding curing accelerator is to increase the reaction rate of the resin composition.
- the main purpose of adding solvent is to change the solid content of the resin composition and modify its viscosity.
- the inorganic filler is at least one of the following: silica (fused or non-fused), aluminum oxide, magnesium oxide, magnesium hydroxide, calcium carbonate, talc, clay, aluminum nitride, boron nitride, aluminum hydroxide, aluminum silicon carbide, silicon carbide, sodium carbonate, titanium dioxide, zinc oxide, zirconium oxide, quartz, diamond powder, diamond-like powder, graphite, or calcined kaolin, and the inorganic filler is spherical or irregular in shape, and can be optionally pretreated with surfactant.
- the inorganic filler is granular powder under 100 ⁇ m in size, preferably 1-20 ⁇ m in size, and most preferably nanogranular powder under 1 ⁇ m in size.
- the aforesaid surfactant could be silane, siloxane, amino silane or polymer thereof.
- the aforesaid toughening agent could be rubber resin, polybutadiene or core-shell polymer.
- the curing accelerator is a catalyst such as Lewis base or Lewis acid, wherein Lewis base includes one or the combination of imidazole, boron trifluoride-amine complex, ethyltriphenyl phosphonium chloride, 2-methylimidazole (2MI), 2-phenyl-1H-imidazole (2PZ), 2-ethyl-4-methylimidazole (2E4MZ), triphenylphosphine (TPP), and 4-dimethylaminopyridine (DMAP), and Lewis acid include metal salt compound, such as the metal salt compound of manganese, iron, cobalt, nickel, copper and zinc.
- Lewis base includes one or the combination of imidazole, boron trifluoride-amine complex, ethyltriphenyl phosphonium chloride, 2-methylimidazole (2MI), 2-phenyl-1H-imidazole (2PZ), 2-ethyl-4-methylimidazole (2E4MZ), triphenylphosphine (TPP), and
- the resin composition of the invention optionally further comprises other types of resin in addition to cyanate ester resin and nitrogen and oxygen containing heterocyclic compound.
- the resin composition could be further added with a curing accelerator to facilitate the bonding between said resin and cyanate ester resin and nitrogen and oxygen containing heterocyclic compound.
- the resin composition further includes an epoxy resin and at least a curing accelerator. The curing accelerator could effectively promote the ring opening of epoxy resin and bonding with cyanate ester resin and nitrogen and oxygen containing heterocyclic compound.
- the aforesaid solvent includes methanol, ethanol, ethylene glycol mono methylether, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, toluene, dimethylbenzene, methoxyethyl acetate, ethoxyethyl acetate, propoxyethyl acetate, ethyl acetate, dimethyl formamide, propylene glycol methyl ether, or mixtures thereof.
- Another object of the invention is to disclose a resin film having the properties of low dielectric constant, flame retardancy, low moisture absorption, and halogen-free that can be used as insulating material for laminate and PCB.
- the resin film of the invention comprises the aforementioned resin composition, wherein the resin composition is heated to become semi-cured.
- the resin composition coated on a polyethylenyl terephthalate (PET) film and heated to form resin film.
- PET polyethylenyl terephthalate
- Yet another object of the invention is to disclose a laminate, comprising at least a metal foil layer and at least an insulating layer, wherein the metal foil layer is made of copper, aluminum, nickel, platinum, silver, gold or alloy thereof, and preferably copper foil.
- a further object of the invention is to disclose a prepreg having the properties of high mechanical strength, low dielectric constant and low dissipation factor, flame retardancy, low moisture absorption, and halogen-free.
- the prepreg comprises a reinforcement material and the aforementioned resin composition, wherein the reinforcement material is impregnated with the resin composition, which becomes semi-cured under high temperature heating.
- the reinforcement material can be fiber material, woven fabric and non-woven fabric, such as fiberglass cloth, which can increase the mechanical strength of the prepreg.
- the reinforcement material can be optionally pre-treated by silane coupling agent or siloxane coupling agent, such as fiberglass cloth pretreated by silane coupling agent.
- the aforementioned prepreg can be cured to form a cured sheet or solid insulating layer under high temperature heating or under high temperature and high pressure condition. If the resin composition contains solvent, the solvent will evaporate in the process of high-temperature heating.
- Yet another object of the invention is to disclose a laminate having the properties of low dielectric constant, flame retardancy, low moisture absorption, high mechanical strength, and halogen-free, and is particularly suitable for use in PCB capable of high-speed, high-frequency signal transmission.
- the invention provides a laminate, comprising two or more metal foil layers and at least an insulating layer, wherein the metal foil is made of copper, aluminum, nickel, platinum, silver, gold or alloy thereof; the insulating layer is formed by curing the aforementioned prepreg under high temperature and high pressure, or by laminating the aforementioned prepreg between two metal foil and then pressing under high temperature and high pressure.
- the laminate described above offers at least once of the following advantages: good flame retardancy, low moisture absorption, low dielectric constant and low dissipation factor, higher thermal conduction, lower thermal expandability, better mechanical strength, and environmentally friendly without containing halogen.
- the laminate may be further formed into a printed circuit board after the circuit fabrication process.
- Yet another object of the invention is to disclose a printed circuit board having the properties of low dielectric constant, flame retardancy, low moisture absorption, high mechanical strength, and halogen-free and is particularly suitable for use in high-speed, high-frequency signal transmission.
- the printed circuit board comprises at least a laminate described above and is fabricated using standard printed circuit board fabrication process.
- a resin composition comprising:
- a resin composition comprising:
- (C) 75 parts by weight of polyphenylene oxide resin (PPO) as shown below, where n is an integer greater than or equal to 1;
- Example 2-2 ⁇ 2-4 (E2-2 ⁇ E2-4) are basically the same as E2-1. The difference is E2-2 used 5 parts by weight of nitrogen and oxygen containing heterocyclic compound; E2-3 used 5 parts by weight of polyphenylene oxide resin; and E2-4 used 5 parts by weight of oligomer of phenylmethane maleimide.
- a resin composition comprising:
- a resin composition comprising:
- a resin film was prepared by mixing uniformly the resin composition disclosed in E2 in a blender and then coating it on a PET sheet, and heating the resin composition into semi-cured state.
- a prepreg (PP) was prepared in the following manner: Mix respectively the resin composition disclosed in E2-1 ⁇ 2-4 uniformly and then place it in an impregnator. Pass a fiberglass cloth through the aforesaid impregnator to impregnate the resin composition thereon, and then heat the resin composition into semi-cured state.
- a laminate comprising a resin film, a copper foil sheet and a circuit board was prepared in the following manner: Superimpose the PET-free surface of resin film as described in E5 on the circuit board; remove the PET sheet, and then superimpose the surface of resin film with PET sheet removed on the copper foil; cure the resin composition under high temperature and high pressure into an insulating layer between the copper foil and the circuit board.
- a laminate comprising four sheets of prepreg as described in E6 and two sheets of copper foil was prepared in the following manner: Laminate in sequence copper foil, four sheets of prepreg and copper foil; cure the four prepreg sheets under high temperature and high pressure into an insulating layer between the two copper foil sheets.
- a printed circuit board comprising a multilayer laminates and a plurality of prepregs was prepared, wherein the laminates are those as described in E8 which form surface circuit through lithography and etching process, and the prepregs are those as described in E6.
- the plurality of laminates and plurality of prepregs were alternately superimposed onto each other between two sheets of copper foil.
- the laminated structure was then pressed under high temperature and high pressure to form a circuit board, which is then made into a printed circuit board using standard printed circuit board process.
- a printed circuit board with main structure as described in Example 9 was prepared, where the difference is that the laminates are bored to form blind holes.
- a resin composition comprising:
- Comparative Examples 2 ⁇ 6 are basically the same as C1. The difference is C2 used 30 parts by weight of nitrogen and oxygen containing heterocyclic compound; C3 used 2 parts by weight of polyphenylene oxide resin; C4 used 80 parts by weight of polyphenylene oxide resin; C5 used 2 parts by weight of oligomer of phenylmethane maleimide;; and C6 used 105 parts by weight of oligomer of phenylmethane maleimide
- the tested items included glass transition temperature (Tg), heat resistance (T288), decomposition temperature of laminate (Td), solder dip test of copper-containing laminate (S/D, solder dip 288° C., 10 seconds, test the number of dip cycles to thermal delamination), solder dip test of copper-free laminate after pressure cooking test (PCT) (pressure cooking at 121° C., 1 hr, then solder dip 288° C., 20 seconds to observe the presence of delamination), moisture absorption (measure the difference between the weights of copper-free laminate before and after PCT (1 hr) to obtain moisture absorption), peeling strength between copper foil and laminate (P/S, half ounce copper foil), dielectric constant (Dk), dissipation factor (Df), flaming test (
- the test results of E2-1 and E2-2 show that increasing the amount of nitrogen and oxygen containing heterocyclic compound could effectively reduce the moisture absorption of the laminate.
- the test results of C1 show that when the content of nitrogen and oxygen containing heterocyclic compound is below 5 parts by weight, the moisture absorption of the laminate is increased to 0.4%.
- the test results of C2 show that when the content of nitrogen and oxygen containing heterocyclic compound is more than 25 parts by weight, the laminate displays poorer heat resistance (as indicated by poorer T288, Td and S/D, and delamination occurs in PCT test).
- test results of E2-1 and E2-3 Based on the test results of E2-1 and E2-3, increasing the amount of polyphenylene oxide resin could lower the Df value.
- the test results of C3 show that when the content of PPO is below 5 parts by weight, the Df of laminate would increase to an unexpected level.
- the test results of C4 show that when the content of PPO is more than 75 parts by weight, the prepreg displays poor (ex. rough) external appearance, thereby resulting in lower process yield, and the S/D testing is also failed.
- the invention meets the three criteria of patentability, i.e. novelty, inventive step and usefulness.
- the resin composition of the invention offers the features of low dielectric constant and low dissipation factor by using specific components at specific proportions, and can be made into prepreg or resin film for application in the printed circuit board.
- using the products derived from the invention could fully meet the current market demands.
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Abstract
Description
- The present invention relates to a resin composition, more particularly, a thermosetting resin composition that can be used in prepreg or the insulating layer of printed circuit board.
- As the communications and bandwidth application technologies evolve rapidly, conventional materials used in the printed circuit board (PCB) industry (e.g. FR-4 laminate) can no longer meet the demands for advanced applications, particularly the demands for high frequency PCB.
- To achieve high-frequency and high-speed transmission of high-frequency PCB while ensuring minimal data loss or interference in the transmission process, the materials of laminate preferably has the electrical properties, thermal resistance, hygroscopic property, mechanical properties, dimensional stability, and chemical resistance needed for the process technology and market applications.
- In terms of electrical properties, major consideration should be given to the dielectric constant and dielectric loss (also called “dissipation factor”) of the material.
- In general, signal transmission speed of the laminate is inversely proportional to the square root of its dielectric constant. That is why the smaller the dielectric constant of the laminate material is better. On the other hand, lower dissipation factor means less loss in signal transmission. Thus materials with low dissipation factor provide better transmission quality.
- Therefore, how to develop materials with low dielectric constant and low dissipation factor and apply them to the manufacturing of high-frequency PCB is a pressing problem that PCB material suppliers need to address at the present time.
- In light of the drawbacks of prior art, the inventor, based on his many years of experience in the industry, develops a resin composition that meet the objectives of low dielectric constant and low dissipation factor.
- The primary object of the invention is to provide a resin composition, which, by using specific components at specific proportions, can offer the properties of low electric constant and low dissipation factor, and can be made into prepreg and used in PCB.
- To achieve the aforesaid object, the invention provides a resin composition, comprising: (A) 100 parts by weight of cyanate ester resin; (B) 5 to 25 parts by weight of nitrogen and oxygen containing heterocyclic compound; (C) 5 to 75 parts by weight of polyphenylene oxide (PPO) resin; and (D) 5 to 100 parts by weight of oligomer of phenylmethane maleimide.
- The aforesaid composition may be used in manufacturing prepreg, laminate and PCB.
- By using specific components at specific proportions, the resin composition of the invention can offer the properties of low electric constant and low dissipation factor, and can be made into prepreg and used in PCB.
- The component (A) cyanate ester resin in the resin composition of the invention comprises at least one selected from a group consisting of the following:
- where X1 and X2 each independently represents at least R, Ar, SO2 or O; R is selected from the group of —C(CH3)2—, —CH(CH3)—, —CH2—, and substituted or unsubstituted dicyclopentadienyl; Ar is selected from the group of substituted or unsubstituted benzene, biphenyl, naphthalene, phenol novolac, bisphenol A, bisphenol A novolac, bisphenol F and bisphenol F novolac function groups; n is an integer greater than or equal to 1; and Y represents hydrogen, an aliphatic functional group or an aromatic functional group.
- The component (B) nitrogen and oxygen containing heterocyclic compound in the resin composition of the invention comprises a ring structure being simultaneously replaced by nitrogen and oxygen, and preferably comprises at least one selected from a group consisting of the following:
- where X3 represents R′ or Ar; R′ is selected from the group of —C(CH3)3, —CH2(CH3), —CH3 and substituted or unsubstituted dicyclopentadienyl; Ar is selected from the group of substituted or unsubstituted benzene, biphenyl, naphthalene, phenol novolac, bisphenol A, bisphenol A novolac, bisphenol F and bisphenol F novolac; X4 and X5 each independently represents R, Ar or —SO2—; R is selected from the group of —C(CH3)2—, —CH(CH3)—, —CH2— and substituted or unsubstituted dicyclopentadienyl; n is an integer greater than or equal to 1; and Y is hydrogen, an aliphatic functional group or an aromatic functional group.
- Through research and experiments, the inventor finds that nitrogen and oxygen containing heterocyclic compound can bond directly with cyanate ester resin. In comparison with prior art where cyanate ester resin could effectively bond with other types of resin in the presence of a catalyst, the resin composition in this invention could engage in crosslinking in the presence or absence of a catalyst.
- In the bonding reaction of nitrogen and oxygen containing heterocyclic compound with cyanate ester resin, increasing temperature could increase the rate of reaction. For example, heating nitrogen and oxygen containing heterocyclic compound and cyanate ester resin in an 150˜190° C. oven for 2 to 10 minutes could accelerate the bonding and form a composition in semi-cured or fully curing state.
- Given the low dielectric constant of cyanate ester resin and the low dissipation factor of nitrogen and oxygen containing heterocyclic compound, the resin composition of the invention possesses the characteristics of low dielectric constant and low dissipation factor. In addition, in the bonding process of nitrogen and oxygen containing heterocyclic compound and cyanate ester resin, the C atom and N atom in functional group —O—C≡N bond directly with respectively O atom and C atom (C atom between O atom and N atom) in the nitrogen-oxygen heterocyclic ring. Therefore, hygroscopic hydroxyl group resulting from the bonding with water molecules will not increase in this bonding process. Consequently, the resin composition of the invention has low hygroscopic property with more than 40% less moisture absorption as compared to general FR4 materials.
- The component (C) polyphenylene oxide resin in the resin composition of the invention comprises at least one selected from a group consisting of the following:
- where X6 is selected from the group of covalent bond, —SO2—, —C(CH3)2—, —CH(CH3)— and —CH2—; Z1 to Z12 each independently represents hydrogen or a methyl group; W represents hydroxyl, ethylenyl, phenyl ethylenyl, propylenyl, butenyl, butadienyl or epoxy function group; and n is an integer greater than or equal to 1.
- Because the polyphenylene oxide resin in this invention could effectively improve the dielectric properties of resin composition, the addition of polyphenylene oxide resin to nitrogen and oxygen containing heterocyclic compound and cyanate ester resin could further lower the dielectric constant and dissipation factor of the resin composition, and its effect is more pronounced at high frequency (e.g. 1GHz to 10 GHz). In addition, because of the difficult flammability of polyphenylene oxide resin, the resin composition of the invention could also meet the UL 94 V-1 fire safety requirement.
- The component (D) oligomer of phenylmethane maleimide in the resin composition of the invention has the following structural formula:
- where n and m each independently represents a positive integer greater than or equal to 1, and Y is hydrogen, an aliphatic functional group or an aromatic functional group.
- The content of each component in the resin composition of the invention is preferably: (A) 100 parts by weight of cyanate ester resin; (B) 5 to 25 parts by weight of nitrogen and oxygen containing heterocyclic compound; (C) 5 to 75 parts by weight of polyphenylene oxide resin; and (D) 5 to 100 parts by weight of oligomer of phenylmethane maleimide, wherein if the content of nitrogen and oxygen containing heterocyclic compound is less than 5 parts by weight, its addition will not produce the effect of lower moisture absorption; if the content of nitrogen and oxygen containing heterocyclic compound is more than 25 parts by weight, the laminate made from the resin composition will show poor thermal resistance; the addition of less than 5 parts by weight of polyphenylene oxide resin will not produce the desired effect, whereas the addition of more than 75 parts by weight of polyphenylene oxide resin will result in poor (ex. rough) appearance of prepreg made from the resin composition; the addition of less than 5 parts by weight of oligomer of phenylmethane maleimide will not produce the desired effect, whereas the addition of more than 100 parts by weight of oligomer of phenylmethane maleimide will increase the costs of the resin composition. The high costs of the resin composition, and prepreg and laminate made thereof will reduce their competitive advantage.
- The invention preferably and optionally includes at least one specific flame retardant compound to further improve the flame retardancy of the resin composition. The optional flame retardant compound includes but is not limited to phosphate compound and nitrogen-containing phosphate compound. More specifically, the flame retardant compound preferably is at least one selected from a group consisting of but not limited to bisphenol diphenyl phosphate, ammonium polyphosphate, hydroquinone bis-(diphenyl phosphate), bisphenol A bis-(diphenylphosphate), tri(2-carboxyethyl)phosphine (TCEP), tri(isopropylchloro)phosphate, trimethyl phosphate (TMP), dimethyl methyl phosphonate (DMMP), resorcinol dixylenylphosphate (RDXP) (ex.: PX-200), melamine polyphosphate, phosphazene (ex.: SPB-100), phosphazo compound, 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) and derivatives or resins thereof, melamine cyanurate, and tri-hydroxy ethyl isocyanurate.
- For example, the flame retardant compound could be a DOPO compound, DOPO resin (e.g. DOPO-HQ, DOPO-PN, DOPO-BPN), or DOPO-based epoxy resin, in which DOPO-BPN could be DOPO-BPAN, DOPO-BPFN, DOPO-BPSN, or other bisphenol novolac compounds with structural formula as shown below:
- where n is an integer greater than or equal to 1; X represents DOPO functional group; Y is covalent bond, an aliphatic functional group or an aromatic functional group; and Z is hydrogen, an aliphatic functional group or an aromatic functional group. In addition, X and Z could bind to any substituting group position on the benzene ring structure and each benzene ring is not limited to having one X or Z substituting group. For example, a benzene ring can have two or more X substituting groups thereon, or two or more Z substituting groups thereon. In addition, not every benzene ring must have both X and Z substituting groups or some benzene rings have respectively X or Z substituting group or have simultaneously X and Z substituting groups, whereas some other benzene rings have neither X nor Z substituting group.
- Adding a flame retardant compound to the resin composition of the invention could increase the flame retardancy of the resin composition and cured products thereof up to UL 94 V-O fire safety level. As such, laminates and PCBs that use the resin composition would possess good flame retardancy.
- On the basis of 100 parts by weight of cyanate ester resin, the added flame retardant compound is preferably 10 to 200 parts by weight. This preferred content markedly improves the flame retardancy of resin composition and cured products thereof without producing any adverse effect on their physical properties.
- In addition, the resin composition of the invention optionally includes at least one selected from a group consisting of epoxy resin, phenolic resin, phenol novolac resin, styrene resin, polybutadiene resin, anhydride crosslinker, and amino crosslinker, and modifications and combinations thereof.
- Wherein, the epoxy resin could be bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, phenol novolac epoxy resin, bisphenol A novolac epoxy resin, o-cresol novolac epoxy resin, trifunctional epoxy resin, tetrafunctional epoxy resin, multifunctional epoxy resin, dicyclopentadiene (DCPD) epoxy resin, phosphorus-containing epoxy resin, p-xylene epoxy resin, naphthalene-based epoxy resin, benzopyran-based epoxy resin, biphenyl novolac epoxy resin, and phenol aralkyl novolac epoxy resin. With the addition of epoxy resin, the crosslinking and thermal resistance properties of the resin composition are further enhanced.
- Wherein, the anhydride crosslinker could be methyl tetrahydro phthalic anhydride (MTHPA), phthalic anhydride (PA), nadic methyl anhydride (NMA), or styrene maleic anhydride (SMA); the amino crosslinker could be polyamide resin, dicyandiamide, diamino diphenylsulfone, diamino diphenyl methane and amino triazine novolac.
- The resin composition of the invention optionally further comprises inorganic filler, surfactant, toughening agent, curing accelerator or solvent additive.
- The main purpose of adding inorganic filler is to increase the thermal conductivity of resin composition to improve its thermal expansion and mechanical strength. The inorganic filler is preferably evenly distributed in the resin composition. The main purpose of adding surfactant is to enable even distribution of inorganic fillers in the resin composition. The main purpose of adding toughening agent is to improve the flexibility of the resin composition. The main purpose of adding curing accelerator is to increase the reaction rate of the resin composition. The main purpose of adding solvent is to change the solid content of the resin composition and modify its viscosity.
- Wherein, the inorganic filler is at least one of the following: silica (fused or non-fused), aluminum oxide, magnesium oxide, magnesium hydroxide, calcium carbonate, talc, clay, aluminum nitride, boron nitride, aluminum hydroxide, aluminum silicon carbide, silicon carbide, sodium carbonate, titanium dioxide, zinc oxide, zirconium oxide, quartz, diamond powder, diamond-like powder, graphite, or calcined kaolin, and the inorganic filler is spherical or irregular in shape, and can be optionally pretreated with surfactant. The inorganic filler is granular powder under 100 μm in size, preferably 1-20 μm in size, and most preferably nanogranular powder under 1 μm in size.
- The aforesaid surfactant could be silane, siloxane, amino silane or polymer thereof.
- The aforesaid toughening agent could be rubber resin, polybutadiene or core-shell polymer.
- The curing accelerator is a catalyst such as Lewis base or Lewis acid, wherein Lewis base includes one or the combination of imidazole, boron trifluoride-amine complex, ethyltriphenyl phosphonium chloride, 2-methylimidazole (2MI), 2-phenyl-1H-imidazole (2PZ), 2-ethyl-4-methylimidazole (2E4MZ), triphenylphosphine (TPP), and 4-dimethylaminopyridine (DMAP), and Lewis acid include metal salt compound, such as the metal salt compound of manganese, iron, cobalt, nickel, copper and zinc.
- The resin composition of the invention optionally further comprises other types of resin in addition to cyanate ester resin and nitrogen and oxygen containing heterocyclic compound. Under the circumstances, the resin composition could be further added with a curing accelerator to facilitate the bonding between said resin and cyanate ester resin and nitrogen and oxygen containing heterocyclic compound. For example, the resin composition further includes an epoxy resin and at least a curing accelerator. The curing accelerator could effectively promote the ring opening of epoxy resin and bonding with cyanate ester resin and nitrogen and oxygen containing heterocyclic compound.
- The aforesaid solvent includes methanol, ethanol, ethylene glycol mono methylether, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, toluene, dimethylbenzene, methoxyethyl acetate, ethoxyethyl acetate, propoxyethyl acetate, ethyl acetate, dimethyl formamide, propylene glycol methyl ether, or mixtures thereof.
- Another object of the invention is to disclose a resin film having the properties of low dielectric constant, flame retardancy, low moisture absorption, and halogen-free that can be used as insulating material for laminate and PCB.
- The resin film of the invention comprises the aforementioned resin composition, wherein the resin composition is heated to become semi-cured. For example, the resin composition coated on a polyethylenyl terephthalate (PET) film and heated to form resin film.
- Yet another object of the invention is to disclose a laminate, comprising at least a metal foil layer and at least an insulating layer, wherein the metal foil layer is made of copper, aluminum, nickel, platinum, silver, gold or alloy thereof, and preferably copper foil. By laminating the resin film disclosed in the invention to at least one sheet of metal foil and then removing the aforesaid PET film and heat curing the resin film and the metal foil under high temperature and high pressure, an insulating layer that adheres closely to the metal foil layer is formed.
- A further object of the invention is to disclose a prepreg having the properties of high mechanical strength, low dielectric constant and low dissipation factor, flame retardancy, low moisture absorption, and halogen-free. The prepreg comprises a reinforcement material and the aforementioned resin composition, wherein the reinforcement material is impregnated with the resin composition, which becomes semi-cured under high temperature heating. The reinforcement material can be fiber material, woven fabric and non-woven fabric, such as fiberglass cloth, which can increase the mechanical strength of the prepreg. In addition, the reinforcement material can be optionally pre-treated by silane coupling agent or siloxane coupling agent, such as fiberglass cloth pretreated by silane coupling agent.
- The aforementioned prepreg can be cured to form a cured sheet or solid insulating layer under high temperature heating or under high temperature and high pressure condition. If the resin composition contains solvent, the solvent will evaporate in the process of high-temperature heating.
- Yet another object of the invention is to disclose a laminate having the properties of low dielectric constant, flame retardancy, low moisture absorption, high mechanical strength, and halogen-free, and is particularly suitable for use in PCB capable of high-speed, high-frequency signal transmission. As such, the invention provides a laminate, comprising two or more metal foil layers and at least an insulating layer, wherein the metal foil is made of copper, aluminum, nickel, platinum, silver, gold or alloy thereof; the insulating layer is formed by curing the aforementioned prepreg under high temperature and high pressure, or by laminating the aforementioned prepreg between two metal foil and then pressing under high temperature and high pressure.
- The laminate described above offers at least once of the following advantages: good flame retardancy, low moisture absorption, low dielectric constant and low dissipation factor, higher thermal conduction, lower thermal expandability, better mechanical strength, and environmentally friendly without containing halogen. The laminate may be further formed into a printed circuit board after the circuit fabrication process.
- Yet another object of the invention is to disclose a printed circuit board having the properties of low dielectric constant, flame retardancy, low moisture absorption, high mechanical strength, and halogen-free and is particularly suitable for use in high-speed, high-frequency signal transmission. Wherein the printed circuit board comprises at least a laminate described above and is fabricated using standard printed circuit board fabrication process.
- To further disclose the invention for implementation by people with common knowledge in the field, a few examples are cited below. However it should be noted that the examples below are meant to further explain the invention and should not be construed as a limitation on the actual applicable scope of the invention, and as such, all modifications and alterations without departing from the spirits of the invention shall remain within the protected scope and claims of the invention.
- The objects, features and effects of the invention are described in detail below with embodiments in reference to the accompanying diagrams.
- The components of resin composition in Examples 2-1˜2-4 are depicted in Table 1, while those of Comparative Examples 1˜6 are depicted in Table 3.
- A resin composition comprising:
- (A) 100 parts by weight of cyanate ester resin as shown below;
- (B) 20 parts by weight of nitrogen and oxygen containing heterocyclic compound as shown below, where X5 is defined the same as above;
- (C) 50 parts by weight of polyphenylene oxide resin, where n is an integer greater than or equal to 1; and
- (D) 50 parts by weight of oligomer of phenylmethane maleimide, where n and m each independently represents an integer greater than or equal to 1 as shown below (product name: BMI-2300).
- A resin composition comprising:
- (A) 100 parts by weight of cyanate ester resin (product name: BA-230S) as shown below;
- (B) 25 parts by weight of nitrogen and oxygen containing heterocyclic compound (Benzoxazine) as shown below;
- (C) 75 parts by weight of polyphenylene oxide resin (PPO) as shown below, where n is an integer greater than or equal to 1;
- (D) 50 parts by weight of oligomer of phenylmethane maleimide as shown below, where n and m each independently represents an integer greater than or equal to 1 (product name: BMI-2300).
- (E) 100 parts by weight of dicyclopentadiene (DCPD) epoxy resin;
- (F) 50 parts by weight of flame retardant (RDXP);
- (G) 0.1 parts by weight of cobalt salt compound (cobalt octanoate);
- (H) 0.2 parts by weight of 2-phenylimidazole (2PZ);
- (I) 50 parts by weight of fused silica;
- (J) 0.4 parts by weight of siloxane; and
- (K) 50 parts by weight of methyl ethyl ketone (MEK).
- Example 2-2˜2-4 (E2-2˜E2-4) Examples 2-2˜2-4 (E2-2˜E2-4) are basically the same as E2-1. The difference is E2-2 used 5 parts by weight of nitrogen and oxygen containing heterocyclic compound; E2-3 used 5 parts by weight of polyphenylene oxide resin; and E2-4 used 5 parts by weight of oligomer of phenylmethane maleimide.
- A resin composition comprising:
- (A) 100 parts by weight of cyanate ester resin as shown below;
- (B) 25 parts by weight of nitrogen and oxygen containing heterocyclic compound as shown below;
- (C) 75 parts by weight of polyphenylene oxide resin as shown below, where n is an integer greater than or equal to 1;
- (D) 50 parts by weight of oligomer of phenylmethane maleimide as shown below, where n and m each independently represents an integer greater than or equal to 1;
- (E) 100 parts by weight of DOPO-BPAN resin;
- (F) 50 parts by weight of phosphazene;
- (G) 50 parts by weight of spherical silica;
- (H) 1 parts by weight of siloxane; and
- (I) 50 parts by weight of MEK.
- A resin composition comprising:
- (A) 100 parts by weight of PPO-modified cyanate ester resin as shown below:
- (B) 25 parts by weight of nitrogen and oxygen containing heterocyclic compound as shown below;
- (C) 50 parts by weight of oligomer of phenylmethane maleimide as shown below, where n and m each independently represents an integer greater than or equal to 1; and
- (D) 50 parts by weight of flame retardant (RDXP).
- A resin film was prepared by mixing uniformly the resin composition disclosed in E2 in a blender and then coating it on a PET sheet, and heating the resin composition into semi-cured state.
- A prepreg (PP) was prepared in the following manner: Mix respectively the resin composition disclosed in E2-1˜2-4 uniformly and then place it in an impregnator. Pass a fiberglass cloth through the aforesaid impregnator to impregnate the resin composition thereon, and then heat the resin composition into semi-cured state.
- A laminate comprising a resin film, a copper foil sheet and a circuit board was prepared in the following manner: Superimpose the PET-free surface of resin film as described in E5 on the circuit board; remove the PET sheet, and then superimpose the surface of resin film with PET sheet removed on the copper foil; cure the resin composition under high temperature and high pressure into an insulating layer between the copper foil and the circuit board.
- A laminate comprising four sheets of prepreg as described in E6 and two sheets of copper foil was prepared in the following manner: Laminate in sequence copper foil, four sheets of prepreg and copper foil; cure the four prepreg sheets under high temperature and high pressure into an insulating layer between the two copper foil sheets.
- Use respectively resin compositions in E2-1˜E2-4 to fabricate laminates according to the process described in E6 and E8. The physical property testing results of the laminates are shown in Table 2 below.
- A printed circuit board comprising a multilayer laminates and a plurality of prepregs was prepared, wherein the laminates are those as described in E8 which form surface circuit through lithography and etching process, and the prepregs are those as described in E6. The plurality of laminates and plurality of prepregs were alternately superimposed onto each other between two sheets of copper foil. The laminated structure was then pressed under high temperature and high pressure to form a circuit board, which is then made into a printed circuit board using standard printed circuit board process.
- A printed circuit board with main structure as described in Example 9 was prepared, where the difference is that the laminates are bored to form blind holes.
- A resin composition comprising:
- (A) 100 parts by weight of cyanate ester resin as shown below (product name: BA-230S);
- (B) 2 parts by weight of nitrogen and oxygen containing heterocyclic compound as shown below;
- (C) 75 parts by weight of polyphenylene oxide resin as shown below, where n is an integer greater than or equal to 1;
- (D) 50 parts by weight of oligomer of phenylmethane maleimide as shown below, where n and m each independently represents an integer greater than or equal to 1 (product name: BMI-2300);
- (E) 100 parts by weight of dicyclopentadiene epoxy resin;
- (F) 50 parts by weight of flame retardant (RDXP);
- (G) 0.1 parts by weight of cobalt salt compound;
- (H) 0.2 parts by weight of 2-phenylimidazole;
- (I) 50 parts by weight of fused silica;
- (J) 0.4 parts by weight of siloxane; and
- (K) 50 parts by weight of MEK.
- Comparative Examples 2˜6 (C2˜C6) are basically the same as C1. The difference is C2 used 30 parts by weight of nitrogen and oxygen containing heterocyclic compound; C3 used 2 parts by weight of polyphenylene oxide resin; C4 used 80 parts by weight of polyphenylene oxide resin; C5 used 2 parts by weight of oligomer of phenylmethane maleimide;; and C6 used 105 parts by weight of oligomer of phenylmethane maleimide
- Use respectively the resin compositions in C1˜C6 to prepare copper clad laminates with the methods described in E6 and E8. Subject the aforesaid copper clad laminates and copper-free laminates after copper foil etching to physical property testing. The tested items included glass transition temperature (Tg), heat resistance (T288), decomposition temperature of laminate (Td), solder dip test of copper-containing laminate (S/D, solder dip 288° C., 10 seconds, test the number of dip cycles to thermal delamination), solder dip test of copper-free laminate after pressure cooking test (PCT) (pressure cooking at 121° C., 1 hr, then solder dip 288° C., 20 seconds to observe the presence of delamination), moisture absorption (measure the difference between the weights of copper-free laminate before and after PCT (1 hr) to obtain moisture absorption), peeling strength between copper foil and laminate (P/S, half ounce copper foil), dielectric constant (Dk), dissipation factor (Df), flaming test (UL94). The test results are shown in Table 4.
- The test results of E2-1 and E2-2 show that increasing the amount of nitrogen and oxygen containing heterocyclic compound could effectively reduce the moisture absorption of the laminate. The test results of C1 show that when the content of nitrogen and oxygen containing heterocyclic compound is below 5 parts by weight, the moisture absorption of the laminate is increased to 0.4%. The test results of C2 show that when the content of nitrogen and oxygen containing heterocyclic compound is more than 25 parts by weight, the laminate displays poorer heat resistance (as indicated by poorer T288, Td and S/D, and delamination occurs in PCT test).
- Based on the test results of E2-1 and E2-3, increasing the amount of polyphenylene oxide resin could lower the Df value. The test results of C3 show that when the content of PPO is below 5 parts by weight, the Df of laminate would increase to an unexpected level. The test results of C4 show that when the content of PPO is more than 75 parts by weight, the prepreg displays poor (ex. rough) external appearance, thereby resulting in lower process yield, and the S/D testing is also failed.
- Based on the test results of E2-1 and E2-4, increasing the amount of oligomer of phenylmethane maleimide could increase the Tg value of the laminate. According to the test results of C5, when the content of oligomer of phenylmethane maleimide is below 5 parts by weight, the Tg value of the laminate will drop below the expected value. According to the test results of C6, the Tg value of the laminate will increase significantly when the content of oligomer of phenylmethane maleimide exceeds 100 parts by weight. But it will also jack up the costs of the resin composition and the laminate that the products will not be cost competitive.
-
TABLE 1 Components E2-1 E2-2 E2-3 E2-4 Cyanate ester resin BA-230S 100 100 100 100 Nitrogen and Benzoxazine 25 5 25 25 oxygen containing heterocyclic compound Polyphenylene PPO 75 75 5 75 oxide resin Maleimide BMI-2300 50 50 50 5 Flame retardant RDXP 50 50 50 50 Epoxy resin DCPD-epoxy 100 100 100 100 Inorganic filler fused silica 50 50 50 50 Siloxane compound Siloxane 0.4 0.4 0.4 0.4 Catalyst Cobalt octanoate 0.1 0.1 0.1 0.1 2PZ 0.2 0.2 0.2 0.2 Solvent MEK 50 50 50 50 -
TABLE 2 Property test Test method E2-1 E2-2 E2-3 E2-4 Tg DSC 181 178 184 173 (° C.) T288 TMA >70 >70 >70 >70 (min) Td TGA (° C.) 391 394 396 392 S/D dip cycles >40 >40 >40 >40 (288° C.) PCT (1 hr) dip 288° C., Pass pass pass pass 20 s Moisture after PCT 0.25 0.38 0.25 0.25 absorption (1 hr) (%) P/S Hoz Cu 6.5 6.6 6.9 6.5 foil Dk 1 GHz 3.75 3.73 3.75 3.75 Df 1 GHz 0.0055 0.0055 0.0063 0.0055 Flaming UL94 V-0 V-0 V-0 V-0 test Cost normal normal normal low Others PP smooth smooth smooth smooth appearance -
TABLE 3 Component C1 C2 C3 C4 C5 C6 Cyanate BA-230S 100 100 100 100 100 100 ester resin Nitrogen and Benzoxazine 2 30 25 25 25 25 Oxygen containing heterocyclic compound Polyphenylene PPO 75 75 2 80 75 75 oxide resin Maleimide BMI-2300 50 50 50 50 2 105 Flame retardant RDXP 50 50 50 50 50 50 Epoxy resin DCPD- 100 100 100 100 100 100 epoxy Inorganic filler Fused silica 50 50 50 50 50 50 Siloxane Siloxane 0.4 0.4 0.4 0.4 0.4 0.4 compound Catalyst Cobalt 0.1 0.1 0.1 0.1 0.1 0.1 octanoate 2PZ 0.2 0.2 0.2 0.2 0.2 0.2 Solvent MEK 50 50 50 50 50 50 -
TABLE 4 Property test Test method C1 C2 C3 C4 C5 C6 Tg DSC(° C.) 178 183 186 175 171 191 T288 TMA (min) >70 24 >70 >70 >70 >70 Td TGA(° C.) 390 381 396 383 390 390 S/D dip cycles(288° C.) >40 13 >40 23 >40 >40 PCT (1 hr) dip 288° C., 20 s pass fail pass pass pass pass Moisture after PCT (1 hr) 0.40 0.25 0.25 0.26 0.25 0.25 absorption (%) P/S Hoz Cu foil 6.6 6.4 6.9 6.2 6.5 6.5 Dk 1 GHz 3.73 3.81 3.86 3.76 3.75 3.75 Df 1 GHz 0.0055 0.0055 0.0064 0.0053 0.0055 0.0055 Flaming test UL94 V-0 V-0 V-0 V-0 V-0 V-0 Cost normal normal normal normal Low High Others PP appearance smooth smooth smooth rough smooth smooth - As described above, the invention meets the three criteria of patentability, i.e. novelty, inventive step and usefulness. In terms of novelty and inventive step, the resin composition of the invention offers the features of low dielectric constant and low dissipation factor by using specific components at specific proportions, and can be made into prepreg or resin film for application in the printed circuit board. In terms of usefulness, using the products derived from the invention could fully meet the current market demands.
- The preferred embodiments of the present invention have been disclosed in the examples. However the examples should not be construed as a limitation on the actual applicable scope of the invention, and as such, all modifications and alterations without departing from the spirits of the invention shall remain within the protected scope and claims of the invention.
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