TWI478981B - Halogen-free resin composition and its application - Google Patents
Halogen-free resin composition and its application Download PDFInfo
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- TWI478981B TWI478981B TW102100222A TW102100222A TWI478981B TW I478981 B TWI478981 B TW I478981B TW 102100222 A TW102100222 A TW 102100222A TW 102100222 A TW102100222 A TW 102100222A TW I478981 B TWI478981 B TW I478981B
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- Prior art keywords
- halogen
- resin composition
- formula
- carbon atoms
- independently represent
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims description 31
- 229920005989 resin Polymers 0.000 claims description 28
- 239000011347 resin Substances 0.000 claims description 28
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 25
- 239000011889 copper foil Substances 0.000 claims description 20
- 239000003063 flame retardant Substances 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 17
- 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 description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- -1 1,3,5-triethoxymethylcyclohexane Chemical compound 0.000 claims description 13
- 229920001955 polyphenylene ether Polymers 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 6
- 239000011256 inorganic filler Substances 0.000 claims description 6
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 6
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 5
- 239000004713 Cyclic olefin copolymer Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000003822 epoxy resin Substances 0.000 description 11
- 230000009477 glass transition Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229920000647 polyepoxide Polymers 0.000 description 11
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000012779 reinforcing material Substances 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000003365 glass fiber Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000008054 signal transmission Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical compound C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-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
- 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 description 3
- 229910000420 cerium oxide Inorganic materials 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229910052863 mullite Inorganic materials 0.000 description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 2
- GRPTWLLWXYXFLX-UHFFFAOYSA-N 1,1,2,2,3,3-hexabromocyclodecane Chemical compound BrC1(Br)CCCCCCCC(Br)(Br)C1(Br)Br GRPTWLLWXYXFLX-UHFFFAOYSA-N 0.000 description 1
- 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
- QMAQLCVJIYANPZ-UHFFFAOYSA-N 2-propoxyethyl acetate Chemical compound CCCOCCOC(C)=O QMAQLCVJIYANPZ-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QEDXSHCYPROEOK-UHFFFAOYSA-N 3-phosphanylpropanoic acid Chemical compound OC(=O)CCP QEDXSHCYPROEOK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229910002706 AlOOH Inorganic materials 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000004114 Ammonium polyphosphate Substances 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- 208000037427 Beta-propeller protein-associated neurodegeneration Diseases 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CPOUOIPAVPTHFR-UHFFFAOYSA-N C1(O)=CC=C(O)C=C1.C1(=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C1=CC=CC=C1.C1(O)=CC=C(O)C=C1 Chemical compound C1(O)=CC=C(O)C=C1.C1(=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C1=CC=CC=C1.C1(O)=CC=C(O)C=C1 CPOUOIPAVPTHFR-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 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
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ASONQZPECNCPCA-UHFFFAOYSA-N P(=O)(OC1(C(C=CC=C1)C)C)(OC1(C(C=CC=C1)C)C)OC1=CC(O)=CC=C1 Chemical compound P(=O)(OC1(C(C=CC=C1)C)C)(OC1(C(C=CC=C1)C)C)OC1=CC(O)=CC=C1 ASONQZPECNCPCA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- IWBUYGUPYWKAMK-UHFFFAOYSA-N [AlH3].[N] Chemical compound [AlH3].[N] IWBUYGUPYWKAMK-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- CAVCGVPGBKGDTG-UHFFFAOYSA-N alumanylidynemethyl(alumanylidynemethylalumanylidenemethylidene)alumane Chemical compound [Al]#C[Al]=C=[Al]C#[Al] CAVCGVPGBKGDTG-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-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
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 1
- 229920001276 ammonium polyphosphate Polymers 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 229910001593 boehmite Inorganic materials 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- PLBFUQVAZLRSRG-UHFFFAOYSA-N cyanic acid;toluene Chemical compound OC#N.CC1=CC=CC=C1 PLBFUQVAZLRSRG-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 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
- 238000010030 laminating Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- NFFIWVVINABMKP-UHFFFAOYSA-N methylidynetantalum Chemical compound [Ta]#C NFFIWVVINABMKP-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 201000007614 neurodegeneration with brain iron accumulation 5 Diseases 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910003468 tantalcarbide Inorganic materials 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 239000011787 zinc oxide Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
- C08G73/0655—Preparatory processes from polycyanurates
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- 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
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- C08K3/34—Silicon-containing compounds
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- 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
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
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Description
本發明涉及一種無鹵素樹脂組合物，尤指一種應用於銅箔基板及印刷電路板之無鹵素樹脂組合物。
為適應世界環保潮流及綠色法規，無鹵素(Halogen-free)為當前全球電子產業之環保趨勢，世界各國及相關電子大廠陸續對其電子產品，制定無鹵素電子產品之量產時程表。歐盟之有害物質限用指令(Restriction of Hazardous Substances,RoHS)實施後，包含鉛、鎘、汞、六價鉻、聚溴聯苯與聚溴二苯醚等物質，已不得用於製造電子產品或其零元件。印刷電路板(Printed Circuit Board,PCB)為電子電機產品之基礎，無鹵素以對印刷電路板為首先重點管制物件，國際組織對於印刷電路板之鹵素含量已有嚴格要求，其中國際電工委員會(IEC)61249-2-21規範要求溴、氯化物之含量必須低於900 ppm，且總鹵素含量必須低於1500 ppm；日本電子迴路工業會(JPCA)則規定溴化物與氯化物之含量限制均為900 ppm；而綠色和平組織現階段大力推動之綠化政策，要求所有之製造商完全排除其電子產品中之聚氯乙烯及溴系阻燃劑，以符合兼具無鉛及無鹵素之綠色電子。因此，材料之無鹵化成為目前業界之重點開發項目。
新時代之電子產品趨向輕薄短小，並適合高頻傳輸，因此電路板之配線走向高密度化，電路板之材料選用走向
更嚴謹之需求。高頻電子組件與電路板接合，為了維持傳輸速率及保持傳輸訊號完整性，電路板之基板材料必須兼具較低之介電常數(dielectric constant,Dk)及介電損耗(又稱損失因數，dissipation factor,Df)。同時，為了在高溫、高濕度環境下依然維持電子組件正常運作功能，電路板也必須兼具耐熱、難燃及低吸水性之特性。環氧樹脂由於接著性、耐熱性、成形性優異，因此廣泛應用於電子零組件及電機機械之覆銅箔積層板或密封材。從防止火災之安全性觀點而言，要求材料具有阻燃性，一般是以無阻燃性之環氧樹脂，配合外加阻燃劑之方式達到阻燃之效果，例如，在環氧樹脂中藉由導入鹵素，尤其是溴，而賦予阻燃性，提高環氧基之反應性。另外，在高溫下經長時間使用後，可能會引起鹵化物之解離，而有微細配線腐蝕之虞。再者使用過後之廢棄電子零組件，在燃燒後會產生鹵化物等有害化合物，對環境亦不友善。為取代上述之鹵化物阻燃劑，有研究使用磷化合物作為阻燃劑，例如添加磷酸酯(中華民國專利公告I238846號)或紅磷(中華民國專利公告322507號)於環氧樹脂組合物中。然而，磷酸酯會因產生水解反應而使酸離析，導致影響其耐遷移性；而紅磷之阻燃性雖高，但在消防法中被指為危險物品，在高溫、潮濕環境下因為會發生微量之膦氣體。
習知之銅箔基板(或稱銅箔積層板)製作之電路板技術中，係利用環氧基樹脂與硬化劑作為熱固性樹脂組合物原料，將補強材(如玻璃纖維布)與該熱固性樹脂組成加熱結合
形成半固化膠片(prepreg)，再將該半固化膠片與上、下兩片銅箔在高溫高壓下壓合而成。現有技術一般使用環氧基樹脂與具有羥基(-OH)之酚醛(phenol novolac)樹脂硬化劑作為熱固性樹脂組成原料，酚醛樹脂與環氧基樹脂結合會使環氧基開環後形成另一羥基，羥基本身會提高介電常數及介電損耗值，且易與水分結合，增加吸濕性。
中華民國專利公告第I297346號揭露一種使用氰酸酯樹脂、二環戊二烯基環氧樹脂、矽石以及熱塑性樹脂作為熱固性樹脂組合物，此種熱固性樹脂組合物具有低介電常數與低介電損耗等特性。然而此製造方法於製作時必須使用含有鹵素(如溴)成份之阻燃劑，例如四溴環己烷、六溴環癸烷以及2,4,6-三(三溴苯氧基)-1,3,5-三氮雜苯，而這些含有溴成份之阻燃劑在產品製造、使用甚至回收或丟棄時都很容易對環境造成污染。為了提高銅箔基板之耐熱難燃性、低介電損耗、低吸濕性、高交聯密度、高玻璃轉化溫度、高接合性、適當之熱膨脹性，環氧樹脂、硬化劑及補強材之材料選擇成了主要影響因素。
就電氣性質而言，主要需考慮者包括材料之介電常數以及介電損耗。一般而言，由於基板之訊號傳送速度與基板材料之介電常數之平方根成反比，因此基板材料之介電常數通常越小越好；另一方面，由於介電損耗越小代表訊號傳遞之損失越少，因此介電損耗較小之材料所能提供之傳輸品質也較為良好。
因此，如何開發出低介電常數、低介電損耗、高耐熱
性和高玻璃轉化溫度之材料，並將其應用於高頻印刷電路板之製造，乃是現階段印刷電路板材料供應商亟欲解決之問題。
鑒於上述現有技術之缺陷，發明人有感其未臻於完善，遂竭其心智悉心研究克服，憑其從事該項產業多年之累積經驗，進而研發出一種無鹵素樹脂組合物，以期達到低介電常數、低介電損耗、高耐熱性和高玻璃轉化溫度之效果。
本發明之主要目之是提供一種無鹵素樹脂組合物，其通過包含特定之組成份及比例，以使可達到低介電常數、低介電損耗、高耐熱性和高玻璃轉化溫度之效果；可製作成半固化膠片或樹脂膜，進而達到可應用於銅箔基板及印刷電路板之目的。
為實現上述目的，本發明提供一種無鹵素樹脂組合物，其包含：(A)100重量份含烯基結構之聚苯醚樹脂(polyphenylene ether resin)；(B)10至50重量份環狀烯烴共聚物(cyclo olefin copolymer,COC)；(C)5至50重量份1,2,4-三乙烯基環己烷樹脂(1,2,4-trivinylcyclohexane resin)及/或1,3,5-三乙氧甲基環己烷樹脂(1,3,5-triethyloxymethyl cyclohexane resin)；及(D)5至150重量份含聚苯醚結構之氰酸酯樹脂。
本發明之無鹵素樹脂組合物中，所述組成份(A)含烯基
結構之聚苯醚樹脂是式一，式二或式三所示化合物之其中一個或其組合：
其中Y是或共價鍵；m和n是大於或等於1之整數；
其中n是6至80之整數；
其中a,b分別獨立是0-30之整數，並且a,b中至少一者不為零；R1
、R2
、R3
、R4
、R5
、R6
及R7
各自獨立表示氫原子、鹵素原子、烷基或苯基；Z是含有至少一個碳原子
之有機基團；-(O-X-O)-表示式四或式五；
其中R8
、R9
、R10
、R14
及R15
各自獨立表示鹵素原子、含六個或更少碳原子之烷基或苯基；R11
、R12
及R13
各自獨立表示氫原子、鹵素原子、含6個或更少碳原子之烷基或苯基；
其中R16
、R17
、R22
及R23
各自獨立表示鹵素原子、含六個或更少碳原子之烷基或苯基；R18
、R19
、R20
及R21
各自獨立表示氫原子、鹵素原子、含六個或更少碳原子之烷基或苯基；A是含有20個或更少碳原子之線性、分枝或環狀烴；其中-(Y-O)-是如式六之部分或如式六部分之任意排列；式六
其中R24
及R25
各自獨立表示鹵素原子、含六個或更少碳原子之烷基或苯基；R26
及R27
各自獨立表示氫原子、鹵素原子、含六個或更少碳原子之烷基或苯基。
更具體而言，式一所示化合物如SABIC Innovative Plastics出售之商品名SA9000之商品；式二所示化合物如晉一化工出售之商品名PP-600之商品，是由SABIC Innovative Plastics出售之商品名SA-120之商品與反應而成；式三所示化合物如中華民國專利公告322507號實施例所示之具體化合物。
本發明之無鹵素樹脂組合物中，所述組成份(B)環狀烯烴共聚物具有以下結構：
其中X和Y是大於或等於1之整數。
更具體而言，所述組成份(B)環狀烯烴共聚物如商品名Topas 5013、Topas 6017、Topas 8007或Topas 6015之商品。
本發明之無鹵素樹脂組合物中，所述組成份(C)是
1,2,4-三乙烯基環己烷樹脂(1,2,4-trivinylcyclohexane resin)或1,3,5-三乙氧甲基環己烷樹脂(1,3,5-triethyloxymethyl cyclohexane resin)。
本發明之無鹵素樹脂組合物中，所述組成份(D)含聚苯醚結構之氰酸酯樹脂(cyanate ester resin)具有以下結構：
其中X6
是共價鍵、-SO2
-、-C(CH3
)2
-、-CH(CH3
)-或-CH2
-；Z5
至Z12
各自獨立是氫或甲基；W為-O-C≡N；n是大於或等於1之整數。
本發明之無鹵素樹脂組合物中，其中進一步包含選自下列群組中之至少一者：阻燃劑、無機填充物、起始劑、阻聚劑和有機溶劑。
所述阻燃劑是磷酸鹽化合物及/或含氮磷酸鹽化合物，但並不以此為限，且以含烯基結構之聚苯醚樹脂為100重量份計算，所述阻燃劑之用量為10至250重量份。
更具體來說，阻燃劑較佳係包含以下化合物中之至少一者：雙酚聯苯磷酸鹽(bisphenol diphenyl phosphate)、聚磷酸銨(ammonium polyphosphate)、對苯二酚-雙-(聯苯基磷酸鹽)(hydroquinone bis-(diphenyl phosphate))、雙酚A-雙-(聯苯基磷酸鹽)(bisphenol A bis-(diphenylphosphate))、三
(2-羧乙基)膦(tri(2-carboxyethyl)phosphine,TCEP)、三(異丙基氯)磷酸鹽、磷酸三甲酯(trimethyl phosphate,TMP)、甲基膦酸二甲酯(dimethyl methyl phosphonate,DMMP)、間苯二酚雙二甲苯基磷酸鹽(resorcinol dixylenylphosphate,RDXP(如PX-200))、聚磷酸三聚氰胺(melamine polyphosphate)、偶磷氮化合物、9,10-二氫-9-氧雜-10-磷菲-10-氧化物(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide,DOPO)及其衍生物或樹脂、三聚氰胺氰尿酸酯(melamine cyanurate)及三-羥乙基異氰尿酸酯(tri-hydroxy ethyl isocyanurate)等，但並不以此為限。舉例來說，阻燃劑可以是DOPO化合物、DOPO樹脂(如DOPO-HQ、DOPO-PN、DOPO-BPN)、DOPO鍵結之環氧樹脂等，其中DOPO-BPN可為DOPO-BPAN、DOPO-BPFN、DOPO-BPSN等雙酚酚醛化合物。
所述無機填充物包含以下化合物中之至少一者：二氧化矽(熔融態、非熔融態、多孔質或中空型)、氧化鋁、氫氧化鋁、氧化鎂、氫氧化鎂、碳酸鈣、氮化鋁、氮化硼、碳化鋁矽、碳化矽、碳酸鈉、二氧化鈦、氧化鋅、氧化鋯、石英、鑽石粉、類鑽石粉、石墨、碳酸鎂、鈦酸鉀、陶瓷纖維、雲母、勃姆石(boehmite,AlOOH)、鉬酸鋅、鉬酸銨、硼酸鋅、磷酸鈣、煅燒滑石、滑石、氮化矽、莫來石、煅燒高嶺土、粘土、鹼式硫酸鎂晶鬚、莫來石晶鬚、硫酸鋇、氫氧化鎂晶鬚、氧化鎂晶鬚、氧化鈣晶鬚、納米碳管、納米氧化矽、其相關無機粉體、或具有有機核外層殼為絕緣
體修飾之粉體粒子中之一者或多者。
所述無機填充物是球形、纖維狀、板狀、粒狀、片狀或針鬚狀，並可選擇性由矽烷偶合劑預處理。
所述無機填充物是粒徑100 μm以下之顆粒粉末，較佳係粒徑1 μm至20 μm之顆粒粉末，更佳係粒徑1 μm以下之納米尺寸顆粒粉末；針鬚狀無機填充物殼是直徑50 μm以下且長度為1至200 μm之粉末。
所述有機溶劑包含以下化合物中之至少一者：甲醇、乙醇、乙二醇單甲醚、丙酮、丁酮(甲基乙基酮)、甲基異丁基酮、環己酮、甲苯、二甲苯、甲氧基乙基乙酸酯、乙氧基乙基乙酸酯、丙氧基乙基乙酸酯、乙酸乙酯、二甲基甲醯胺、二甲基乙醯胺、丙二醇甲基醚。
本發明之另一目之是提供一種半固化膠片(prepreg)，其具有低介電常數與低介電損耗、高玻璃轉化溫度、高耐熱性及不含鹵素等特性。據此，本發明所揭露之半固化膠片可包含補強材及前述無鹵素樹脂組合物，其中所述無鹵素樹脂組合物以含浸等方式附著於該補強材上，並經過高溫加熱形成半固化態。其中，補強材可以是纖維材料、織布及不織布，如玻璃纖維布等，其可增加所述半固化膠片之機械強度。此外，所述補強材可選擇性經過矽烷偶合劑或矽氧烷偶合劑進行預處理，如經矽烷偶合劑預處理玻璃纖維布。
本發明之另一目的是提供一種銅箔基板(copper clad laminate)，其具有低介電常數與低介電損耗、高玻璃轉化
溫度、高耐熱性及不含鹵素等特性，且特別適用於高速度高頻率訊號傳輸電路板。據此，本發明提供一種銅箔基板，其包含兩個或兩個以上銅箔及至少一個絕緣層。其中，銅箔可進一步包含銅與鋁、鎳、鉑、銀、金等至少一種金屬合金；絕緣層由前述半固化膠片在高溫高壓下固化而成，如將前述半固化膠片疊合於兩個銅箔間且在高溫高壓下進行壓合而成。
本發明之又一目的是提供一種印刷電路板(printed circuit board)，其具有低介電常數與低介電損耗、高玻璃轉化溫度、高耐熱性及不含鹵素等特性，且適用於高速度高頻率訊號傳輸。其中，該電路板包含至少一個前述銅箔基板。
為進一步揭露本發明，以使本發明所屬技術領域中具有通常知識者可據以實施，以下通過幾個實施例進一步說明本發明。然而應注意的是，以下實施例僅用以對本發明做進一步說明，並非用以限制本發明之實施範圍，且本發明所屬技術領域中具有通常知識者在不違背本發明之精神下所進行之任何修飾及變化，均屬於本發明之範圍。
為充分瞭解本發明之目的、特徵及功效，茲藉由下述具體實施例，對本發明做詳細說明，說明如後。
分別將實施例1至4、比較例1至2之樹脂組合物組成份列表於表一，組合物物理特性列表於表二。
將5g含聚苯醚結構之氰酸酯樹脂(BTP-6020S)溶解於195g甲苯中，製備成氰酸酯-甲苯溶液待用。於1000mL反應瓶中依次加入100g乙烯基聚苯醚樹脂(OPE-2st)、20g環狀烯烴共聚物(COC 5013)、15g 1,2,4-三乙烯基環己烷樹脂、90g中空二氧化矽(B-6C)、10g熔融二氧化矽(SC-2050MB)、0.02g辛酸鋅、40g含磷阻燃劑(OP-935)、1g橡膠改質樹脂(Ricon 257)和2g過氧化苯甲醯(BPO)，然後將BTP-6020S之甲苯溶液加入上述反應瓶中，得到樹脂組合物。
製作方法與實施例1相同，配方組成份和物性見表一和表二。
將40g乙烯橡膠(Ricon 257)溶解於160g甲苯中，製備成20%之甲苯溶液待用。於1000 mL反應瓶中依序加入100g聯苯型環氧樹脂(NC-3000H)、26g苯乙烯馬來酸酐共聚物(EF-60)、30g氮氧雜環化合物(benzoxazine,Bz)、90g勃姆石(AOH60)、10g煅燒滑石粉(SG-95)、4g過氧化二異丙苯(DCP)、25g含磷阻燃劑(OP-935)、0.5g密著劑(TSH)、0.2g觸媒(2E4MI)，然後將200g含乙烯橡膠之甲苯溶液加入上述反應瓶中，得到樹脂組合物。
製作方法與比較例1相同，配方組成份和物性見表一
和表二。
將上述實施例1-4及比較例1-2樹脂組合物，分批於攪拌槽中混合均勻後加入到含浸槽中，再將玻璃纖維布通過上述含浸槽，使樹脂組合物附著於玻璃纖維布，再進行加熱烘烤成半固化態而得半固化膠片。
將上述分批製得之半固化膠片，取同一批半固化膠片四張及兩張18 μm銅箔，按銅箔、四片半固化膠片、銅箔順序進行疊合，再於真空條件下經過220℃壓合2小時形成銅箔基板，其中四片半固化膠片固化形成兩銅箔間絕緣層。
分別將上述含銅箔基板及銅箔蝕刻後不含銅基板做物性量測，物性量測項目包含玻璃轉化溫度(Tg)、介電常數(Dk越低越佳)、介電損耗(Df越低越佳)、含銅基板浸錫測試(solder dip 288℃，10秒，測耐熱回數，S/D)、剝離強度。分別將實施例1至4、比較例1至2樹脂組合物量測結果列於表二。
由實施例1-4資料顯示，按照本發明申請專利範圍內之樹脂組成份，所有物性都可達到預期規格水準。與實施例1、2相比較，實施例3和4由於添加了較多含聚苯醚結構之氰酸酯樹脂，以使增加了組合物之玻璃轉化溫度。
比較實施例1-4與比較例1-2，本發明之組合物在玻璃轉化溫度、介電常數、介電損耗、耐熱性、剝離強度等方面都表現出了較好之性能(Dk與Df值越低表示介電性能越好)。
如上所述，本發明滿足專利對新穎性、進步性和產業利用性之要求。以新穎性和進步性而言，本發明無鹵素樹脂組合物，其由於包含特定組成份及比例，以使可達到低介電常數、低介電損耗、高玻璃轉化溫度及高耐熱性；可製作成半固化膠片或樹脂膜，進而達到可應用於銅箔基板及印刷電路板之目的；就產業利用性而言，利用本發明所衍生之產品，應當可以充分滿足目前市場之需求。
本發明在上文中已以較佳實施例揭露，但本領域中具有通常知識者應理解的是，該實施例僅用於描述本發明，而不應理解為限制本發明範圍。應注意的是，凡是與該實施例等效之變化與置換，均應視為涵蓋於本發明之申請專利範圍內。因此，本發明保護範圍當以申請專利範圍所界定之為準。
Claims (10)
- 一種無鹵素樹脂組合物，其包含：(A)100重量份含烯基結構之聚苯醚樹脂；(B)10至50重量份環狀烯烴共聚物；(C)5至50重量份1,2,4-三乙烯基環己烷樹脂及/或1,3,5-三乙氧甲基環己烷樹脂；及(D)5至150重量份含聚苯醚結構之氰酸酯樹脂。
- 如申請專利範圍第1項所述之無鹵素樹脂組合物，其中所述含烯基結構之聚苯醚樹脂是式一，式二或式三所示化合物之其中一者或其組合：
- 如申請專利範圍第1項所述之無鹵素樹脂組合物，其中所述環狀烯烴共聚物具有以下結構：
- 如申請專利範圍第1項所述之無鹵素樹脂組合物，其中所述含聚苯醚結構之氰酸酯樹脂具有以下結構：
- 如申請專利範圍第1項所述之無鹵素樹脂組合物，其中進一步包含選自下列群組中之至少一者：阻燃劑、無機填充物、起始劑、阻聚劑和有機溶劑。
- 如申請專利範圍第5項所述之無鹵素樹脂組合物，其中所述阻燃劑為磷酸鹽化合物及/或含氮磷酸鹽化合物。
- 如申請專利範圍第6項所述之無鹵素樹脂組合物，其中以所述含烯基結構之聚苯醚樹脂為100重量份計算，所述阻燃劑之用量為10至250重量份。
- 一種半固化膠片，其包含如申請專利範圍第1至7項中任一項所述之樹脂組合物。
- 一種銅箔基板，其包含如申請專利範圍第8項所述之半固化膠片。
- 一種印刷電路板，其包含如申請專利範圍第9項所述之銅箔基板。
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| TWI646142B (zh) * | 2012-12-21 | 2019-01-01 | 台光電子材料股份有限公司 | Resin composition and copper foil substrate and printed circuit board using same |
| TWI667276B (zh) * | 2014-05-29 | 2019-08-01 | 美商羅傑斯公司 | 具改良耐燃劑系統之電路物質及由其形成之物件 |
| CN105542457B (zh) * | 2014-10-30 | 2017-12-15 | 台光电子材料(昆山)有限公司 | 一种低介电耗损树脂组成物及其制品 |
| CN105801838B (zh) * | 2014-12-31 | 2018-08-21 | 台光电子材料(昆山)有限公司 | 聚苯醚树脂、聚苯醚树脂的制造方法、聚苯醚预聚物及树脂组成物 |
| CN104774476B (zh) * | 2015-03-10 | 2018-03-09 | 广东生益科技股份有限公司 | 含磷阻燃组合物以及使用它的含磷聚苯醚树脂组合物、预浸料和层压板 |
| CN106609031B (zh) * | 2015-10-22 | 2018-11-27 | 广东生益科技股份有限公司 | 一种聚苯醚树脂组合物以及含有它的预浸料、层压板和印制电路板 |
| US10233365B2 (en) | 2015-11-25 | 2019-03-19 | Rogers Corporation | Bond ply materials and circuit assemblies formed therefrom |
| US10023672B2 (en) * | 2016-05-24 | 2018-07-17 | Elite Material Co., Ltd. | Polyphenylene oxide prepolymer, method of making the same, resin composition and product made therefrom |
| CN108912578B (zh) * | 2018-06-13 | 2021-02-02 | 金发科技股份有限公司 | 一种改性环状聚烯烃材料及其应用 |
| CN110776739B (zh) * | 2019-09-05 | 2022-04-05 | 艾蒙特成都新材料科技有限公司 | 一种高速基板用热固性树脂组合物、覆铜板及其制备方法 |
| CN111050469A (zh) * | 2019-12-30 | 2020-04-21 | 江苏联鑫电子工业有限公司 | 一种高耐热性高cti无铅覆铜板及其制备方法 |
| CN113444355B (zh) * | 2020-03-24 | 2023-04-14 | 中山台光电子材料有限公司 | 树脂组合物及其制品 |
| US20230272213A1 (en) * | 2020-07-17 | 2023-08-31 | Panasonic Intellectual Property Management Co., Ltd. | Resin composition, prepreg, film provided with resin, metal foil provided with resin, metal-clad laminate, and wiring board |
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| JPS62249960A (ja) * | 1986-04-21 | 1987-10-30 | Sumitomo Chem Co Ltd | ポリフエニレンオキシドのシアン酸エステル |
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| US20120214009A1 (en) * | 2006-02-17 | 2012-08-23 | Yasuyuki Mizuno | Thermosetting resin composition of semi-ipn composite, and varnish, prepreg and metal clad laminated board using the same |
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| US7364672B2 (en) * | 2004-12-06 | 2008-04-29 | Arlon, Inc. | Low loss prepregs, compositions useful for the preparation thereof and uses therefor |
| JP5463110B2 (ja) * | 2009-09-24 | 2014-04-09 | ナミックス株式会社 | カバーレイフィルム |
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- 2012-10-24 CN CN201210410056.5A patent/CN103772957B/zh active Active
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2013
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- 2013-01-11 US US13/739,428 patent/US20140113118A1/en not_active Abandoned
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| JPS62249960A (ja) * | 1986-04-21 | 1987-10-30 | Sumitomo Chem Co Ltd | ポリフエニレンオキシドのシアン酸エステル |
| US20120214009A1 (en) * | 2006-02-17 | 2012-08-23 | Yasuyuki Mizuno | Thermosetting resin composition of semi-ipn composite, and varnish, prepreg and metal clad laminated board using the same |
| TW200823246A (en) * | 2006-09-15 | 2008-06-01 | Gen Electric | Poly(arylene ether) composition, method and article |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103772957B (zh) | 2016-03-16 |
| US20140113118A1 (en) | 2014-04-24 |
| TW201416395A (zh) | 2014-05-01 |
| CN103772957A (zh) | 2014-05-07 |
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