TW201725210A - 一種磷腈化合物、預浸板及複合金屬基板 - Google Patents
一種磷腈化合物、預浸板及複合金屬基板 Download PDFInfo
- Publication number
- TW201725210A TW201725210A TW105123275A TW105123275A TW201725210A TW 201725210 A TW201725210 A TW 201725210A TW 105123275 A TW105123275 A TW 105123275A TW 105123275 A TW105123275 A TW 105123275A TW 201725210 A TW201725210 A TW 201725210A
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- Prior art keywords
- substituted
- unsubstituted
- group
- substrate
- phosphazene compound
- Prior art date
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- -1 Phosphazene compound Chemical class 0.000 title claims abstract description 30
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 12
- 239000002184 metal Substances 0.000 title claims abstract description 12
- 239000002131 composite material Substances 0.000 title claims abstract description 11
- 239000003822 epoxy resin Substances 0.000 claims abstract description 22
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 19
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 33
- 229910052802 copper Inorganic materials 0.000 claims description 31
- 239000010949 copper Substances 0.000 claims description 31
- 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 27
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- 125000004437 phosphorous atom Chemical group 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 8
- 230000000269 nucleophilic effect Effects 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- DZKXDEWNLDOXQH-UHFFFAOYSA-N 1,3,5,2,4,6-triazatriphosphinine Chemical compound N1=PN=PN=P1 DZKXDEWNLDOXQH-UHFFFAOYSA-N 0.000 claims description 5
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 5
- 239000011188 CEM-1 Substances 0.000 claims description 4
- 239000011190 CEM-3 Substances 0.000 claims description 4
- 101100257127 Caenorhabditis elegans sma-2 gene Proteins 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002015 acyclic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
- 239000012434 nucleophilic reagent Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- LTNCYKRVIPCLLU-UHFFFAOYSA-N 1,2,3,4,5,6-hexahydro-1,3,5,7,2,4,6,8-tetrazatetraphosphocine Chemical compound N1=PNPNPNP1 LTNCYKRVIPCLLU-UHFFFAOYSA-N 0.000 claims description 2
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 239000004917 carbon fiber Substances 0.000 claims description 2
- 125000005587 carbonate group Chemical group 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 239000011889 copper foil Substances 0.000 claims description 2
- 239000003365 glass fiber Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 238000001465 metallisation Methods 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 150000007942 carboxylates Chemical group 0.000 claims 1
- 239000003989 dielectric material Substances 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 31
- 238000010521 absorption reaction Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000012038 nucleophile Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000004843 novolac epoxy resin Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229960002809 lindane Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000007344 nucleophilic reaction Methods 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000008054 signal transmission Effects 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical group [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- LOZAIRWAADCOHQ-UHFFFAOYSA-N triphosphazene Chemical compound PNP=NP LOZAIRWAADCOHQ-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/659—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having three phosphorus atoms as ring hetero atoms in the same ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/09—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
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Abstract
本發明關於一種磷腈化合物、預浸料及複合金屬基板。該磷腈化合物具有式(I)所示的分子結構。本發明係藉由採用特定組成的M基團得到該磷腈化合物,由含有該磷腈化合物的環氧樹脂組合物製備所得之複合金屬基板具有低介電性,良好的耐熱性及機械性能,係一種具有較大的經濟性及環保友善之低介電材料。
Description
本發明屬於低介電材料技術領域,尤其關於一種磷腈化合物、預浸板及複合金屬基板。
以手機、電腦、攝影機、電子遊戲機為代表的電子產品、以空調、冰箱、電視影像、音響用品等為代表的家用、辦公電器產品以及其他領域使用的各種產品,為了安全,很大部分的產品都要求其具備低介電性及耐熱性。
就電氣性質而言,主要需考慮的因素還包含材料的介電常數以及介電損耗。一般而言,由於基板的訊號傳送速度與基板材料的介電常數的平方根成反比,故基板材料的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的損失越少,故介電損耗較小的材料所能提供的傳輸品質也較為良好。
因此,如何開發出具有低介電常數以及低介電損耗的材料,並將其應用於高頻印刷電路板的製造,乃是現階段印刷電路板材料領域亟待解決的問題。
有鑒於此,本發明第一方面提供一種磷腈化合物,該磷腈化合物具有低介電性,良好的耐熱性及機械性能,此外,該磷腈化合物具有成本低的優勢。
為了實現上述目的,本發明採用如下技術手段:
一種磷腈化合物,其具有如式(I)所示的分子結構:
式(I)中,R1為取代或未取代的芳香烴基或取代或未取代的脂肪烴基;R2、R3、R6及R7獨立地為滿足其化學環境的任意有機基團;R4、R5獨立地為任意惰性親核基團;M為環三磷腈基M1、環四以上磷腈基M2或非環狀聚磷腈基M3中的任意一種或其至少兩種的組合;n及m為大於等於零的整數,且n及m不同時為零;a、b為大於等於零的整數,且a+b+2等於M基團上磷原子個數的2倍。
n及m為大於零的整數,例如1、2、3、4、5、6、7等,且n及m不同時為零。
a、b為大於等於零的整數,例如0、1、2、3、4、5、6、7
等,且a+b+2等於M基團上磷原子個數的2倍,即保證M上磷原子達到化合價為五價的飽和狀態。
在本發明中a、b用於表示R4、R5基團的個數,R4、R5基團與M基團中的磷原子相連。
在本發明中,前述滿足其化學環境係指能夠與其相鄰的原子相連,得到穩定的化學連接鍵。
理想地,R1為取代或未取代的直鏈亞烷基、取代或未取代的支鏈亞烷基、取代或未取代的亞環烷基、取代或未取代的亞芳基、取代或未取代的亞雜芳基、取代或未取代的亞芳基亞烷基、取代或未取代的亞烷基亞芳基、取代或未取代的亞環烷基亞芳基、取代或未取代的亞雜芳基亞烷基或取代或未取代的亞烷基亞雜芳基中的任意一種。
理想地,R2及R7獨立地為取代或未取代的直鏈亞烷基、取代或未取代的支鏈亞烷基、取代或未取代的亞環烷基、取代或未取代的亞芳基、取代或未取代的亞雜芳基、取代或未取代的亞芳基亞烷基、取代或未取代的亞烷基亞芳基、取代或未取代的亞環烷基亞芳基或取代或未取代的亞烷基亞雜芳基中的任意一種。
具體地,R1、R2及R7可獨立地為但不限於-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-或中的任意一種。
理想地,R3及R6獨立地為取代或未取代的直鏈烷基或支鏈烷基、取代或未取代的環烷基、取代或未取代的芳基、取代或未取代的雜芳基、取代或未取代的芳烷基、取代或未取代的雜芳基烷基中的任意一種。
理想地,R4及R5獨立地為取代或未取代的烷氧基、取代或未
取代的環烷氧基、取代或未取代的芳氧基、取代或未取代的芳基烷氧基、取代或未取代的烷基芳氧基、取代或未取代的雜芳基烷氧基、取代或未取代的烷基雜芳氧基、取代或未取代的羧酸酯基、取代或未取代的碳酸酯基、取代或未取代的磺酸酯基或取代或未取代的膦酸酯基中的任意一種或至少兩種的組合。
在本發明中,所記載之惰性親核基團,係指在常規反應條件下不具有活潑的化學反應活性,不容易與其他物質發生反應的基團,利用此等反應性基團可將碳鏈進行封端,因此也稱為封端基團。例如在本發明中,前述惰性親核基團可為-OCH3、-Ph(苯環)或-COOCH3等。
本發明所提供的係一種無鹵磷腈化合物,因此,在本發明的式(I)結構中,所有基團以及基團的取代基均不含有鹵素。
在本發明中所記載之親核試劑即指,可與鹵代磷腈發生親核取代反應的親核試劑。在親核取代反應過程中,親核試劑脫去離去基團,親核基團進攻鹵代磷腈中的鹵素原子,親核基團與M相連。例如,當採用甲醇CH3OH作為親核試劑與鹵代磷腈發生親核取代反應時,CH3OH脫去H+,親核基團甲氧基CH3O-取代鹵代磷腈中的鹵素原子,與磷腈中的-P相連。
在本發明中,取代或未取代的直鏈烷基或支鏈烷基理想為取代或未取代的C1~C12(例如C1、C2、C3、C4、C5、C6、C7、C8、C9、C10或C11)直鏈烷基或支鏈烷基,更理想為C1~C8直鏈烷基或支鏈烷基,當碳原子數為1時即為甲基,碳原子數為2時,即為乙基。
取代或未取代的環烷基理想為取代或未取代的C3~C12(例如C4、C5、C6、C7、C8、C9、C10或C11)的環烷基。
取代或未取代的烷氧基理想為取代或未取代的C1~C12(例如C2、C3、C4、C5、C6、C7、C8、C9、C10或C11)的烷氧基。
取代或未取代的環烷氧基理想為取代或未取代的C3~C12(例如C4、C5、C6、C7、C8、C9、C10或C11)的環烷氧基。
取代或未取代的芳基理想為C7-C13(例如C8、C9、C10、C11或C12)烷基芳基。理想為苯基、萘基、、或等。苯基的實例如聯苯基、三聯苯基、苯甲基、苯乙基或苯丙基等。
取代或未取代的雜芳烷基理想為C7-C13(例如C8、C9、C10、C11或C12)雜芳烷基,理想為五元或六元雜芳基,更理想為取代或未取代的呋喃基或吡啶基。
取代或未取代的芳烷基理想為C7-C13(例如C8、C9、C10、C11或C12)芳烷基。
取代或未取代的芳氧基理想為C7-C13(例如C8、C9、C10、C11或C12)芳氧基。
取代或未取代的芳基烷氧基理想為C7-C13(例如C8、C9、C10、C11或C12)芳基烷氧基。
取代或未取代的烷基芳氧基理想為C7-C13(例如C8、C9、C10、C11或C12)烷基芳氧基。
取代或未取代的雜芳基烷氧基理想為C7-C13(例如C8、C9、C10、C11或C12)雜芳基烷氧基。
取代或未取代的烷基雜芳基氧基理想為C7-C13(例如C8、C9、C10、C11或C12)烷基雜芳基氧基。
取代或未取代的直鏈亞烷基理想為C1-C12(例如C2、C3、C4、C5、C6、C7、C8、C9、C10或C11)的直鏈亞烷基。
取代或未取代的支鏈亞烷基理想為C1-C12(例如C2、C3、C4、C5、C6、C7、C8、C9、C10或C11)的支鏈亞烷基。
取代或未取代的亞芳基理想為C6-C13(例如C7、C8、C9、C10、C11或C12)的亞芳基。
取代或未取代的亞雜芳基理想為C5-C13(例如C6、C7、C8、C9、C10、C11或C12)的亞雜芳基。
取代或未取代的亞烷基亞芳基理想為C7-C13(例如C8、C9、C10、C11或C12)亞烷基亞芳基。
取代或未取代的亞芳基亞烷基理想為C7-C13(例如C8、C9、C10、C11或C12)亞芳基亞烷基。
取代或未取代的亞烷基亞雜芳基理想為C6-C13(例如C7、C8、C9、C10、C11或C12)亞烷基亞雜芳基。
取代或未取代的亞雜芳基亞烷基理想為C6-C13(例如C7、C8、C9、C10、C11或C12)亞雜芳基亞烷基。
本發明所使用的術語“取代的”係指指定原子上的任一個或複數個氫原子被選自指定組的取代基取代,條件為前述指定原子不超過正常價態,並且取代的結果係產生穩定的化合物。當取代基為氧代基團或酮基(即=O)時,那麼原子上的2個氫原子被取代。酮取代基在芳香環上不存
在。“穩定的化合物”係指能夠足夠強健地由反應混合物中分離至有效的純度並配製成有效的化合物。
在本發明中,理想地,M1結構為:
M2結構為:
其中,x大於等於4;M3結構為:
其中,y大於等於3。
注意,M1、M2結構式的表示中,所出現符號僅係對“環狀”結構的一種示意。M1、M2及M3中中P原子上連接的鍵僅代表三者中取代基取代發生在P原子上,不可理解為甲基的表示。
理想地,M表示主要由不飽和磷及氮原子構成的磷氮骨架的
基團,即磷腈基團,具體為:M包含至少50wt%的環三磷腈基M1、至多48wt%的環四以上磷腈基M2以及至多48wt%的非環狀聚磷腈基M3。
在本發明中,M1含量至少為50wt%,即M1含量可為50wt~100wt%,M1為主體成分。當M1含量為100wt%時,則不含有M2及M3。本發明典型但非限制性的M1的含量可為50wt%、51wt%、55wt%、58wt%、60wt%、65wt%、70wt%、74wt%、75wt%、80wt%、85wt%、90wt%、92wt%、95wt%、98wt%或100wt%。
在本發明中,M2含量至多為30wt%,即指,M2含量可為0~30wt%。當M2含量為0wt%時,即指,不含有M2。本發明典型但非限制性的M2含量可為0wt%、2wt%、5wt%、8wt%、11wt%、14wt%、16wt%、17wt%、19wt%、20wt%、22wt%、25wt%、27wt%、28wt%或29wt%。
在本發明中,M3含量至多為45wt%,即指,M3含量可為0~30wt%。當M3含量為0wt%時,即指,不含有M3。本發明典型但非限制性的M3含量可為0wt%、2wt%、5wt%、8wt%、10wt%、12wt%、14wt%、16wt%、18wt%、20wt%、23wt%、25wt%、27wt%、28wt%、30wt%、32wt%、35wt%、38wt%、40wt%、43wt%或45wt%。
在本發明中,M1、M2及M3質量百分比之和為100%。
在本發明中,若M1含量小於50wt%,或者M2多於48wt%,則與環氧樹脂反應後的生成物在使用中均會損害耐熱性、耐水性及機械性能。若M3含量大於45%,則與環氧樹脂反應後的生成物在使用中將有可能因黏度過大而導致使用不便,以及因分子量過大而使其性能受到損害等不良結果。
理想地,本發明所記載之磷腈化合物為具有以下結構的化合物中的一種或至少兩種的組合:
其中M為環三磷腈基。
在本發明的式(I)中,封端基團R3、R4、R5、R6可均為芳香類封端基團,例如R4、R5可為、或等基團,R3、R6可為苯基、聯苯基、苄基等,例如式(I)所示化合物可為:
或
等等,其中M為環三磷腈基。
另一方面,本發明提供一種磷腈化合物的製備方法,由該方法製備的磷腈化合物具有良好的耐熱性、良好的機械性能,且介電常數低。
一種製備上述磷腈化合物的方法,將磷腈氯化物與羧酸類以及酚或醇類親核試劑進行親核取代反應所得到。
磷腈氯化物指M-Cla+b+2,親核試劑係指式(I)中與M基團連接的基團所對應的親核試劑,例如當R1為時,可實現與磷腈氯化物
發生親核取代反應將連接至M的磷原子上的親核試劑為
、當R3為-CH2CH2-時,可實現與磷腈氯化物發生親核取代反應將-O-CH2CH2-O-連接至M的磷原子上的親核試劑可為OHCH2CH2OH;同樣的方法可實現R2、R5、R6、R7與M的磷原子的連接。
在前述親核取代反應中,磷腈氯化物中的氯被取代。親核反應可採用本領域習知的方法來完成,例如可參考“聚磷腈的研究進展,張宏偉等,材料導報2010年第24卷第7期”。親核反應中使用的催化劑的具體實例有氯化鋅、氯化鎂、氯化鋁等金屬氯化物、三氟化硼及其絡合物、氫氧化鈉等路易士鹼。此等催化劑可一種或多種混合使用,本發明中並無特別的規定。在此“磷腈氯化物”指式(I)中M基團與Cl相連接而成的化合物。至於磷腈氯化物可使用習知的溶劑、催化劑於習知的反應路線合成,亦可使用五氯化磷與氯化銨按照習知的方法合成出來氯化磷腈化合物後,經過
物理方法處理提純或不提純直接製造,其PCl5+NH4Cl→1/n(NPCl2)n+4 HCl,該反應產物中主要為三聚體(PNCl2)3(亦即六氯環三磷腈)及四聚體(PNCl2)4,反應產物再通過60℃真空中緩慢昇華可得到純的六氯環三磷腈。氯代環四以上磷腈及氯代非環狀聚磷腈亦可藉由已有技術製備得到。
在親核試劑與磷腈氯化物的反應中,可先採用一種親核試劑與磷腈氯化物反應,一部份取代磷腈氯化物中的氯,然後再用另一種親核試劑與磷腈氯化物反應,以得到式(I)結構的磷腈化合物。並且可藉由控制物質之間的物質量關係,來得到結構中含有一個M基團或含有複數個M基團的磷腈化合物。
另一方面,本發明提供一種具有低介電性能,良好的耐熱性以及良好的機械性能的環氧樹脂組合物。
該環氧樹脂組合物包含本發明所記載之磷腈化合物。
至於環氧樹脂組合物的環氧樹脂、固化劑、其它填料可採用習知的環氧樹脂、固化劑、填料。
前述環氧樹脂組合物除前述含磷腈的聚酯外,亦可包含其他聚酯。
另一方面,本發明提供一種預浸板,其係由上述環氧樹脂組合物含浸或塗布於基材而成。
基材可為玻璃纖維基材、聚酯基材、聚醯亞胺基材、陶瓷基材或碳纖維基材等。
在此,含浸或塗布的具體工藝條件無特別限定。預浸板”也為本領域技術人員所熟知的“黏結片”。
一種複合金屬基板,其包含一張以上如前述之預浸板依次進行表面覆金屬層重疊、壓合而成。
此表面覆金屬層的材質為鋁、銅、鐵及其任意組合的合金。
複合金屬基板的具體實例有CEM-1覆銅板、CEM-3覆銅板、FR-4覆銅板、FR-5覆銅板、CEM-1鋁基板、CEM-3鋁基板、FR-4鋁基板或FR-5鋁基板。
一種柔性覆銅板,前述柔軟性覆銅板包含一張以上前述預浸板以及覆於疊合後的預浸板一側或兩側的銅箔。
一種線路板,於上述的複合金屬基板的表面加工線路而成。
環氧樹脂組合物的原料藉由固化在複合金屬基板上形成具有良好低介電性能以及耐熱性的塗層,可提高線路板,例如電子產業、電氣、電器產業、交通運輸、航空航太、玩具產業等需要線路板的機器、設備、儀器、儀錶等產業的廣泛應用。
上述術語“×××基或基團”指×××化合物分子結構中脫去一個或複數個氫原子或其它原子或原子團後剩餘的部份。
本發明係藉由採用特定組成的M基團得到本發明所記載之磷腈化合物,使得由其組成的環氧樹脂組合物的固化物具有低介電性、良好的耐熱性、機械性能,係一種還具有較大的經濟性及環保友善型的低介電材料。採用該阻燃性化合物得到的覆銅板的介電常數(1GHz)為3.28-3.33,介電損耗(1GHz)為0.005-0.006,Tg可達到175℃及以上,T-剝
離強度可達到1.90kg/mm2及以上,層間剝離強度可達到1.64kg/mm2及以上,飽和吸水率可達到0.35%以下。
以下透過具體實施方式來進一步說明本發明的技術手段。
在以下實施例中,所用原料磷腈氯化物(如六氯環三磷腈)可根據本發明所記載之合成方法或本領域已知的合成方法合成得到,其餘原料可藉由商業購買得到。
實施例1
本實施例的磷腈化合物的結構式如下:
其製備方法如下:帶有攪拌裝置的三口2000ml玻璃反應器裡投入六氯環三磷腈1mol、丙酮200ml、甲醇鈉4mol,乙二醇1mol,一邊攪拌、一邊通氮氣,升溫到60℃,用60min滴入20%氫氧化鈉溶液620g,保持60℃溫度,攪拌反應8小時,反應完成後,用物理的方法去除體系中無機成分及水分,滴加3mL 98%的濃硫酸,並加入丁二酸1mol,在40℃攪拌反應5小時,而後加入乙醇1mol,繼續攪拌反應2小時,反應後,用物理方法去除體系中的雜質及水分,蒸餾掉體系中溶劑,得到上述結構的酯當量為180g/eq的酯化物A 1mol。
對得到的化合物A進行核磁共振氫譜表徵,結果如下:
1H NMR(CDCl3,500MHz):δ 4.15-4.22(m,4H,COOC H 2 ),3.83(m,2H,COOCH2C H 2O),3.42(s,12H,OCH 3),2.58-2.60(m,4H,COC H 2C H 2CO),2.1(m,3H,COC H 3),1.63(m,2H,CH3C H 2O),1.0(m,3H,C H 3CH2O)。
紅外譜圖特徵峰的位置:酯羰基1730-1740cm-1,酯基的C-O-C 1200cm-1,磷腈骨架中P=N鍵的特徵吸收峰1217cm-1,磷腈骨架中P-N 874cm-1,甲基醚的吸收峰2995.3cm-1,P-O-C鍵吸收峰1035cm-1,CH2-O的吸收峰2983cm-1。
以前述酯化物A 90g作為固化劑加入環氧當量為200g/eq的鄰甲酚醛環氧樹脂100g,固化促進劑2-甲基咪唑0.2g,製備環氧樹脂組合物。採用該環氧樹脂組合物按照通用的覆銅板製作程序製得符合國家標準、UL等標準的標準覆銅板樣品,命名為a覆銅板,測試a覆銅板的性能,其結果在表1中表示。
實施例2
本實施例的磷腈化合物的結構式如下:
其製備方法如下:帶有攪拌裝置的三口2000ml玻璃反應器裡投入對苯二酚1mol、苯甲酸1mol,丙酮200ml,滴加3mL 98%的濃硫酸,進行酯化反應1h,而後加入六氯環三磷腈1mol、苯酚4mol,一邊攪拌、一邊通氮氣、一升溫到60℃,用60min滴入20%氫氧化鈉溶液621g,保持60℃溫度,攪拌反應10個小時,反
應完成後,用物理的方法去除體系中無機成分及水分,滴加3mL 98%的濃硫酸,並加入1mol對苯二甲酸,繼續反應3小時,而後再加入六氯環三磷腈1mol,繼續反應5小時後,加入苯酚4mol,對苯二酚1mol,繼續反應8小時,反應完成後,用物理的方法去除體系中無機成分及水分,滴加3mL 98%的濃硫酸,並加入苯甲酸1mol,反應2小時。反應後,用物理方法去除體系中的雜質及水分,蒸餾掉體系中溶劑,得到上述結構的酯當量為410g/eq的酯化物B 1mol。
對得到的化合物B進行核磁共振氫譜表徵,結果如下:1H NMR(CDCl3,500MHz):δ 8.28-8.32(m,4H,),7.4-8.1
(m,10H,),6.8-7.0(S,48H,及中的氫)。
紅外譜圖特徵峰的位置:酯羰基1730-1740cm-1,酯基的C-O-C 1200cm-1,磷腈骨架中P=N鍵的特徵吸收峰1217cm-1,磷腈骨架中P-N 874cm-1,P-O-C鍵吸收峰1035cm-1,對位取代苯環860-790cm-1。
以上述酯化物B 205g作為固化劑加入環氧當量200g/eq的鄰甲酚醛環氧樹脂100g,固化促進劑2MI 0.2g,製備環氧樹脂組合物。採用該環氧樹脂組合物按照通用的覆銅板製作程序製得符合國家標準、UL等標準的標準覆銅板樣品,命名為b覆銅板,測試b覆銅板的性能,其結果在表1中表示。
實施例3
本實施例的磷腈化合物的結構式如下:
其製備方法如下:帶有攪拌裝置的三口2000ml玻璃反應器裡投入乙二醇1mol、乙酸1mol,丙酮200ml,滴加3mL 98%的濃硫酸,進行酯化反應1h,而後加入六氯環三磷腈1mol、甲醇鈉4mol,一邊攪拌、一邊通氮氣、一升溫到60℃,用60min滴入20%氫氧化鈉溶液620g,保持60℃溫度,攪拌反應15個小時,反應完成後,用物理的方法去除體系中無機成分及水分,滴加3mL 98%的濃硫酸,並加入對苯二甲酸1mol,繼續保持60℃,攪拌反應3小時,而後再加入1mol六氯環三磷腈,繼續反應3小時,而後加入甲醇鈉4mol,繼續反應5小時,加入對苯二酚1mol,繼續反應4小時,反應完成後,用物理的方法去除體系中無機成分及水分,滴加3mL 98%的濃硫酸,並加入乙酸1mol,反應3小時。反應後,用物理方法去除體系中雜質及水分,蒸餾掉體系中溶劑,得到上述結構之酯當量為255g/eq的酯化物C 1mol。
對得到的化合物C進行核磁共振氫譜表徵,結果如下:1H NMR(CDCl3,500MHz):δ 8.28-8.32(m,4H,),
6.7-6.9(m,4H,),4.32(m,2H,COOC H 2 CH2O),3.83(m,2H,COOCH2C H 2O),3.42(s,24H,OC H 3),2.1(m,6H,COC H 3)。
紅外譜圖特徵峰的位置:酯羰基1730-1740cm-1,酯基的C-O-C 1200cm-1,磷腈骨架中P=N鍵的特徵吸收峰1217cm-1,磷腈骨架中P-N 874cm-1,甲基醚的吸收峰2995.3cm-1,P-O-C鍵吸收峰1035cm-1,CH2-O的吸收峰2983cm-1,對位取代苯環860-790cm-1。
以上述酯化物C 128g作為固化劑加入環氧當量1200g/eq的鄰甲酚醛環氧樹脂100g,固化促進劑2MI 0.2g,製備環氧樹脂組合物。採用該環氧樹脂
組合物按照通用的覆銅板製作程序製得符合國家標準、UL等標準的標準覆銅板樣品,命名為c覆銅板,測試c覆銅板的性能,其結果在表1中表示。
實施例4
本實施例的磷腈化合物的結構式如下:
其製備方法如下:帶有攪拌裝置的三口2000ml玻璃反應器裡投入對苯二酚1mol、乙酸1mol,丙酮200ml,滴加3mL 98%的濃硫酸,進行酯化反應1h,而後加入六氯環三磷腈1mol、甲醇鈉4mol,一邊攪拌、一邊通氮氣、一升溫到60℃,用60min滴入20%氫氧化鈉溶液621g,保持60℃溫度,攪拌反應10個小時,反應完成後,用物理的方法去除體系中無機成分及水分,滴加3mL 98%的濃硫酸,並加入1mol對苯二甲酸,繼續反應3小時,而後再加入六氯環三磷腈1mol,繼續反應5小時後,加入甲醇鈉4mol,對苯二酚1mol,繼續反應8小時,反應完成後,用物理的方法去除體系中無機成分及水分,滴加3mL 98%的濃硫酸,並加入乙酸1mol,反應2小時。反應後,用物理方法去除體系中的雜質及水分,蒸餾掉體系中溶劑,得到上述結構之酯當量為250g/eq的酯化物D 1mol。
對得到的化合物D進行核磁共振氫譜表徵,結果如下:1H NMR(CDCl3,500MHz):δ 8.28-8.32(m,4H,),6.7-6.9(m,8H,),3.42(s,24H,OC H 3),2.1(m,6H,COC H 3)。
紅外譜圖特徵峰的位置:酯羰基1730-1740cm-1,酯基的C-O-C 1200
cm-1,磷腈骨架中P=N鍵的特徵吸收峰1217cm-1,磷腈骨架中P-N 874cm-1,甲基醚的吸收峰2995.3cm-1,P-O-C鍵吸收峰1035cm-1,CH2-O的吸收峰2983cm-1,對位取代苯環860-790cm-1。
以上述酯化物D 125g作為固化劑加入環氧當量200g/eq的鄰甲酚醛環氧樹脂100g,固化促進劑2MI 0.2g,製備環氧樹脂組合物。採用該環氧樹脂組合物按照通用的覆銅板製作程序製得符合國家標準、UL等標準的標準覆銅板樣品,命名為d覆銅板,測試d覆銅板的性能,其結果在表-1中表示。
比較例1
環氧當量為200g/eq的鄰甲基酚醛環氧樹脂200g,加入酚羥基當量為105g/eq的線型酚醛樹脂固化劑105g及作為阻燃劑的六苯氧基磷腈70g以及0.2g的2-甲基咪唑,用適量的丁酮溶解成溶液,用標準玻璃布,按照常規的製作方法,得到含樹脂量為50%的覆銅板e,覆銅e的各項性能在表1中表示。
比較例2
取環氧當量為200g/eq的鄰甲基酚醛環氧樹脂200g,加入具有如式(1)結構的樹脂化合物220g,酯當量為220g/eq以及作為阻燃劑的六苯氧基磷腈70g及0.2g的吡啶,用適量的丁酮溶解成溶液,用標準玻璃布,按照常規的製作方法,得到含樹脂量為50%的覆銅板f。覆銅f的各項性能在表-1中表示。
實施例及比較例的測試結果如下表1所示(鑒於具體測試方法已為本領域技術人員所熟知,在此對方法不再詳述):
由表1可看出,本發明採用含有式(I)所示的分子結構的化合物作為固化劑製備的樹脂組合物,使得由其製備得到的覆銅板的介電常數(1GHz)為3.28-3.33,介電損耗(1GHz)為0.005-0.006,Tg可達到175℃及以上,T-剝離強度可達到1.90kg/mm2及以上,層間剝離強度可達到1.64kg/mm2及以上,飽和吸水率可達到0.35%以下,明顯優於比較例覆銅板的性能。
申請人聲明,本發明透過上述實施例來說明本發明的工藝方法,但本發明並不侷限於上述工藝步驟,即不意味著本發明必須依賴上述工藝步驟才能實施。所屬技術領域的技術人員應該明瞭,對本發明的任何改進,對本發明所選用原料的等效替換及輔助成分的添加、具體方式的選擇等,均落在本發明的保護範圍及公開範圍之內。
Claims (10)
- 一種磷腈化合物,其係具有式(I)所示之分子結構:
- 如申請專利範圍第1項所記載之磷腈化合物,其中,R1為取代或未取代的直鏈亞烷基、取代或未取代的支鏈亞烷基、取代或未取代的亞環烷基、取代或未取代的亞芳基、取代或未取代的亞雜芳基、取代或未取代的亞芳基亞烷基、取代或未取代的亞烷基亞芳基、取代或未取代的亞環烷基亞芳基、取代或未取代的亞雜芳基亞烷基或取代或未取代的亞烷基亞雜芳基中的任意一種;理想地,R2及R7獨立地為取代或未取代的直鏈亞烷基、取代或未取代的支鏈亞烷基、取代或未取代的亞環烷基、取代或未取代的亞芳基、取代或未取代的亞雜芳基、取代或未取代的亞芳基亞烷基、取代或未取代的亞烷基亞芳基、取代或未取代的亞環烷基亞芳基、取代或未取代的亞雜芳基 亞烷基或取代或未取代的亞烷基亞雜芳基中的任意一種;理想地,R3及R6獨立地為取代或未取代的直鏈烷基或支鏈烷基、取代或未取代的環烷基、取代或未取代的芳基、取代或未取代的雜芳基、取代或未取代的芳烷基或取代或未取代的雜芳基烷基中的任意一種;理想地,R4及R5獨立地為取代或未取代的烷氧基、取代或未取代的環烷氧基、取代或未取代的芳氧基、取代或未取代的芳基烷氧基、取代或未取代的烷基芳氧基、取代或未取代的雜芳基烷氧基、取代或未取代的烷基雜芳氧基、取代或未取代的羧酸酯基、取代或未取代的碳酸酯基、取代或未取代的磺酸酯基或取代或未取代的膦酸酯基中的任意一種或至少兩種的組合。
- 如申請專利範圍第1或2項所記載之磷腈化合物,其中,M1結構為:
- 一種如申請專利範圍第1至3項中任一項所記載之磷腈化合物之製備方法,其特徵係將磷腈氯化物與親核試劑進行親核取代反應而得到。
- 一種環氧樹脂組合物,其特徵係其包含申請專利範圍第1至3項中任一項所記載之磷腈化合物。
- 一種預浸板,其特徵係於,其由如申請專利範圍第5項所記載之環氧樹脂組合物含浸或塗布於基材而成。
- 如申請專利範圍第6項所記載之預浸板,其中,前述基材為玻璃纖維基材、聚酯基材、聚醯亞胺基材、陶瓷基材或碳纖維基材。
- 一種複合金屬基板,其特徵係其包含一張以上如申請專利範圍第6或7項所記載之預浸板依次進行表面覆金屬層、重疊、壓合而成;理想地,前述表面覆金屬層的材質為鋁、銅、鐵及其任意組合的合金;理想地,前述複合金屬基板為CEM-1覆銅板、CEM-3覆銅板、FR-4覆銅板、FR-5覆銅板、CEM-1鋁基板、CEM-3鋁基板、FR-4鋁基板或FR-5鋁基板。
- 一種柔性覆銅板,其特徵係其包含一張以上如申請專利範圍第6或7項所記載之預浸板及覆於叠合後之預浸板一側或兩側的銅箔。
- 一種線路板,其特徵係其由申請專利範圍第8項所記載之複合金屬基板的表面加工線路而成。
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