WO2018186476A1 - トリアゾールシラン化合物、該化合物の合成方法およびその利用 - Google Patents
トリアゾールシラン化合物、該化合物の合成方法およびその利用 Download PDFInfo
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- WO2018186476A1 WO2018186476A1 PCT/JP2018/014628 JP2018014628W WO2018186476A1 WO 2018186476 A1 WO2018186476 A1 WO 2018186476A1 JP 2018014628 W JP2018014628 W JP 2018014628W WO 2018186476 A1 WO2018186476 A1 WO 2018186476A1
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- surface treatment
- resin
- treatment liquid
- copper
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- -1 Triazole silane compound Chemical class 0.000 title claims abstract description 114
- 238000000034 method Methods 0.000 title claims abstract description 88
- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 49
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 4
- 238000004381 surface treatment Methods 0.000 claims abstract description 123
- 239000000463 material Substances 0.000 claims abstract description 95
- 239000000126 substance Substances 0.000 claims abstract description 77
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 33
- 239000007788 liquid Substances 0.000 claims description 130
- 229920005989 resin Polymers 0.000 claims description 119
- 239000011347 resin Substances 0.000 claims description 119
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 100
- 239000010949 copper Substances 0.000 claims description 87
- 229910052802 copper Inorganic materials 0.000 claims description 86
- 229910052751 metal Inorganic materials 0.000 claims description 69
- 239000002184 metal Substances 0.000 claims description 69
- 229910010272 inorganic material Inorganic materials 0.000 claims description 57
- 239000011147 inorganic material Substances 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 239000000243 solution Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 31
- 239000007864 aqueous solution Substances 0.000 claims description 24
- 229910000881 Cu alloy Inorganic materials 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- 150000002739 metals Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000000919 ceramic Substances 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 229910045601 alloy Inorganic materials 0.000 claims description 11
- 239000000956 alloy Substances 0.000 claims description 11
- 239000003822 epoxy resin Substances 0.000 claims description 10
- 229920000647 polyepoxide Polymers 0.000 claims description 10
- 239000004065 semiconductor Substances 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 239000010703 silicon Substances 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 229920001721 polyimide Polymers 0.000 claims description 9
- 239000009719 polyimide resin Substances 0.000 claims description 9
- 229920005672 polyolefin resin Polymers 0.000 claims description 9
- 229920002050 silicone resin Polymers 0.000 claims description 9
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 8
- 229910001431 copper ion Inorganic materials 0.000 claims description 8
- 229920002577 polybenzoxazole Polymers 0.000 claims description 8
- 229910052718 tin Inorganic materials 0.000 claims description 8
- 239000011135 tin Substances 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 claims description 6
- 229910002113 barium titanate Inorganic materials 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 6
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 6
- 239000010936 titanium Substances 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- 239000004925 Acrylic resin Substances 0.000 claims description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052737 gold Inorganic materials 0.000 claims description 5
- 239000010931 gold Substances 0.000 claims description 5
- 239000011810 insulating material Substances 0.000 claims description 5
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000011282 treatment Methods 0.000 description 46
- 239000010408 film Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 25
- 238000012360 testing method Methods 0.000 description 24
- 239000000758 substrate Substances 0.000 description 21
- 239000003960 organic solvent Substances 0.000 description 17
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 239000011889 copper foil Substances 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000853 adhesive Substances 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 9
- 238000007747 plating Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000009713 electroplating Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000007822 coupling agent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000005530 etching Methods 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 6
- 235000012431 wafers Nutrition 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 238000007654 immersion Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000005370 alkoxysilyl group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000001099 ammonium carbonate Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000007772 electroless plating Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical compound NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000007788 roughening Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
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- XYYXDARQOHWBPO-UHFFFAOYSA-N 3,5-dimethyl-1h-1,2,4-triazole Chemical compound CC1=NNC(C)=N1 XYYXDARQOHWBPO-UHFFFAOYSA-N 0.000 description 3
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 3
- XGWWZKBCQLBJNH-UHFFFAOYSA-N 3-methylsulfanyl-1h-1,2,4-triazol-5-amine Chemical compound CSC1=NN=C(N)N1 XGWWZKBCQLBJNH-UHFFFAOYSA-N 0.000 description 3
- LKSKYTPSWHNROI-UHFFFAOYSA-N 5-methyl-3-octyl-1h-1,2,4-triazole Chemical compound CCCCCCCCC1=NNC(C)=N1 LKSKYTPSWHNROI-UHFFFAOYSA-N 0.000 description 3
- NYMLZIFRPNYAHS-UHFFFAOYSA-N 5-phenyl-1h-1,2,4-triazole Chemical compound C1=NNC(C=2C=CC=CC=2)=N1 NYMLZIFRPNYAHS-UHFFFAOYSA-N 0.000 description 3
- FGKGSFAVSCHLQC-UHFFFAOYSA-N 6-bromohexyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCCBr FGKGSFAVSCHLQC-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
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- 150000004679 hydroxides Chemical class 0.000 description 3
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- 150000007524 organic acids Chemical class 0.000 description 3
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
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- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- CQWRPTXGOCIGHR-UHFFFAOYSA-N 1-(3-triethoxysilylpropyl)-1,2,4-triazole-3,5-diamine Chemical compound NC1=NN(C(=N1)N)CCC[Si](OCC)(OCC)OCC CQWRPTXGOCIGHR-UHFFFAOYSA-N 0.000 description 2
- JQYKIYZXGNLNOK-UHFFFAOYSA-N 1-(3-trimethoxysilylpropyl)-1,2,4-triazol-3-amine Chemical compound NC1=NN(C=N1)CCC[Si](OC)(OC)OC JQYKIYZXGNLNOK-UHFFFAOYSA-N 0.000 description 2
- XLOQWDWLDZOECO-UHFFFAOYSA-N 1-(3-trimethoxysilylpropyl)-1,2,4-triazole-3,5-diamine Chemical compound NC1=NN(C(=N1)N)CCC[Si](OC)(OC)OC XLOQWDWLDZOECO-UHFFFAOYSA-N 0.000 description 2
- POGCBDGWOGRLBY-UHFFFAOYSA-N 1-(6-triethoxysilylhexyl)-1,2,4-triazol-3-amine Chemical compound NC1=NN(C=N1)CCCCCC[Si](OCC)(OCC)OCC POGCBDGWOGRLBY-UHFFFAOYSA-N 0.000 description 2
- JEZLRCNKSFKPNA-UHFFFAOYSA-N 3-(3,5-dimethyl-1,2,4-triazol-1-yl)propyl-trimethoxysilane Chemical compound CC1=NN(C(=N1)C)CCC[Si](OC)(OC)OC JEZLRCNKSFKPNA-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
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- FPOSCXQHGOVVPD-UHFFFAOYSA-N chloromethyl(trimethoxy)silane Chemical compound CO[Si](CCl)(OC)OC FPOSCXQHGOVVPD-UHFFFAOYSA-N 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical class [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- HMDRAGZZZBGZJC-UHFFFAOYSA-N n-[3-[3-aminopropoxy(dimethoxy)silyl]propyl]-1-phenylprop-2-en-1-amine Chemical compound NCCCO[Si](OC)(OC)CCCNC(C=C)C1=CC=CC=C1 HMDRAGZZZBGZJC-UHFFFAOYSA-N 0.000 description 1
- QELJHCBNGDEXLD-UHFFFAOYSA-N nickel zinc Chemical compound [Ni].[Zn] QELJHCBNGDEXLD-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- OFNHPGDEEMZPFG-UHFFFAOYSA-N phosphanylidynenickel Chemical compound [P].[Ni] OFNHPGDEEMZPFG-UHFFFAOYSA-N 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 239000005060 rubber Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- WIJVUKXVPNVPAQ-UHFFFAOYSA-N silyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)O[SiH3] WIJVUKXVPNVPAQ-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- GRJISGHXMUQUMC-UHFFFAOYSA-N silyl prop-2-enoate Chemical class [SiH3]OC(=O)C=C GRJISGHXMUQUMC-UHFFFAOYSA-N 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical class NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- MPPFOAIOEZRFPO-UHFFFAOYSA-N triethoxy(3-iodopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCI MPPFOAIOEZRFPO-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- YOQZHCWDFNAXLS-UHFFFAOYSA-N triethoxy-[10-(3-hexylsulfanyl-1,2,4-triazol-1-yl)decyl]silane Chemical compound C(CCCCC)SC1=NN(C=N1)CCCCCCCCCC[Si](OCC)(OCC)OCC YOQZHCWDFNAXLS-UHFFFAOYSA-N 0.000 description 1
- LTRBOHSNVPSZBE-UHFFFAOYSA-N triethoxy-[2-(3-methyl-1,2,4-triazol-1-yl)ethyl]silane Chemical compound CC1=NN(C=N1)CC[Si](OCC)(OCC)OCC LTRBOHSNVPSZBE-UHFFFAOYSA-N 0.000 description 1
- JHPHIDFDRDCNBA-UHFFFAOYSA-N triethoxy-[3-(3-ethylsulfanyl-5-propan-2-yl-1,2,4-triazol-1-yl)propyl]silane Chemical compound C(C)SC1=NN(C(=N1)C(C)C)CCC[Si](OCC)(OCC)OCC JHPHIDFDRDCNBA-UHFFFAOYSA-N 0.000 description 1
- AHUKRCVMYYOBNZ-UHFFFAOYSA-N triethoxy-[3-(3-hexylsulfanyl-1,2,4-triazol-1-yl)propyl]silane Chemical compound C(CCCCC)SC1=NN(C=N1)CCC[Si](OCC)(OCC)OCC AHUKRCVMYYOBNZ-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- YZYKUXVEADNJJU-UHFFFAOYSA-N trimethoxy-[10-(3-propan-2-yl-1,2,4-triazol-1-yl)decyl]silane Chemical compound C(C)(C)C1=NN(C=N1)CCCCCCCCCC[Si](OC)(OC)OC YZYKUXVEADNJJU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- WNLMYKWTVGDCDR-UHFFFAOYSA-N trimethoxy-[3-(3-methyl-5-phenyl-1,2,4-triazol-1-yl)propyl]silane Chemical compound CC1=NN(C(=N1)C1=CC=CC=C1)CCC[Si](OC)(OC)OC WNLMYKWTVGDCDR-UHFFFAOYSA-N 0.000 description 1
- ROWJDRNXCNBONF-UHFFFAOYSA-N trimethoxy-[3-(3-methylsulfanyl-1,2,4-triazol-1-yl)propyl]silane Chemical compound CSC1=NN(C=N1)CCC[Si](OC)(OC)OC ROWJDRNXCNBONF-UHFFFAOYSA-N 0.000 description 1
- SQIPLLYHBGTVEH-UHFFFAOYSA-N trimethoxy-[3-(3-propan-2-ylsulfanyl-1,2,4-triazol-1-yl)propyl]silane Chemical compound C(C)(C)SC1=NN(C=N1)CCC[Si](OC)(OC)OC SQIPLLYHBGTVEH-UHFFFAOYSA-N 0.000 description 1
- BDIAKSNWKMDQPS-UHFFFAOYSA-N trimethoxy-[3-(3-propyl-1,2,4-triazol-1-yl)propyl]silane Chemical compound C(CC)C1=NN(C=N1)CCC[Si](OC)(OC)OC BDIAKSNWKMDQPS-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- XOSFHIROHSQNAP-UHFFFAOYSA-N trimethoxy-[4-(5-methyl-1,2,4-triazol-1-yl)butyl]silane Chemical compound CC1=NC=NN1CCCC[Si](OC)(OC)OC XOSFHIROHSQNAP-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
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- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
- C09J9/02—Electrically-conducting adhesives
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
- H01L23/3157—Partial encapsulation or coating
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
- H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L24/18—High density interconnect [HDI] connectors; Manufacturing methods related thereto
- H01L24/19—Manufacturing methods of high density interconnect preforms
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0346—Organic insulating material consisting of one material containing N
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/46—Manufacturing multilayer circuits
- H05K3/4644—Manufacturing multilayer circuits by building the multilayer layer by layer, i.e. build-up multilayer circuits
- H05K3/4673—Application methods or materials of intermediate insulating layers not specially adapted to any one of the previous methods of adding a circuit layer
- H05K3/4676—Single layer compositions
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- 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
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
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- 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
- B32B2457/00—Electrical equipment
- B32B2457/14—Semiconductor wafers
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2203/00—Indexing scheme relating to apparatus or processes for manufacturing printed circuits covered by H05K3/00
- H05K2203/07—Treatments involving liquids, e.g. plating, rinsing
- H05K2203/0779—Treatments involving liquids, e.g. plating, rinsing characterised by the specific liquids involved
- H05K2203/0786—Using an aqueous solution, e.g. for cleaning or during drilling of holes
- H05K2203/0789—Aqueous acid solution, e.g. for cleaning or etching
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2203/00—Indexing scheme relating to apparatus or processes for manufacturing printed circuits covered by H05K3/00
- H05K2203/07—Treatments involving liquids, e.g. plating, rinsing
- H05K2203/0779—Treatments involving liquids, e.g. plating, rinsing characterised by the specific liquids involved
- H05K2203/0786—Using an aqueous solution, e.g. for cleaning or during drilling of holes
- H05K2203/0793—Aqueous alkaline solution, e.g. for cleaning or etching
Definitions
- the present invention relates to a novel triazole silane compound, a surface treatment liquid using the triazole silane compound, a surface treatment method, and use thereof.
- a substance composed of an organic substance and silicon is used as a component of the silane coupling agent.
- This substance has different types of functional groups in the molecule, and functions as an intermediary between organic materials and inorganic materials that are not familiar to each other. Therefore, it is an indispensable drug for the development and production of composite materials.
- Patent Document 1 discloses a nitrogen-containing heterocyclic ring such as triazole or thiadiazole and a silyl such as a trimethoxysilyl group or a triethoxysilyl group as components of a silane coupling agent used for a primer for bonding glass or metal and rubber.
- a silane coupling agent used for a primer for bonding glass or metal and rubber.
- Patent Document 2 proposes 1N-trimethoxysilylpropyl-1,2,4-triazole as a silane compound used as a corrosion inhibitor for aluminum and magnesium alloys.
- An object of the present invention is to provide a novel triazole silane compound, a synthesis method thereof, and a silane coupling agent containing the novel triazole silane compound as a component. It is another object of the present invention to provide a surface treatment liquid, a surface treatment method and a bonding method of different materials using the triazolesilane compound.
- X 1 and X 2 are the same or different and each represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a phenyl group, a benzyl group, an amino group, or an alkyl group having 1 to 6 carbon atoms.
- m represents an integer of 1 to 12.
- R represents a methyl group or an ethyl group, except that X 1 and X 2 are hydrogen atoms at the same time.
- Hal represents a chlorine atom, a bromine atom or an iodine atom.
- a silane coupling agent comprising a triazole silane compound represented by the following chemical formula (IV) as a component.
- X 1 and X 2 are the same or different and each represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a phenyl group, a benzyl group, an amino group, or an alkyl group having 1 to 6 carbon atoms.
- m represents an integer of 1 to 12
- n represents 0 or an integer of 1 to 3
- R represents a methyl group or an ethyl group, provided that X 1 and X 2 are hydrogen atoms at the same time. Except in cases.
- X 1 and X 2 are the same or different and each represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a phenyl group, a benzyl group, an amino group, or an alkyl group having 1 to 6 carbon atoms.
- m represents an integer of 1 to 12
- n represents 0 or an integer of 1 to 3
- R represents a methyl group or an ethyl group, provided that X 1 and X 2 are hydrogen atoms at the same time. Except in cases.
- the surface treatment liquid according to [4] which is used for treating at least one surface selected from the group consisting of metals, inorganic materials, and resin materials.
- the surface according to [5] or [6], wherein the metal is at least one selected from the group consisting of copper, aluminum, titanium, nickel, tin, iron, silver, gold, and alloys thereof. Treatment liquid.
- the surface treatment solution according to [5] or [6], wherein the metal is copper or a copper alloy.
- the ceramic is at least one selected from the group consisting of alumina, silicon carbide, aluminum nitride, silicon nitride, and barium titanate.
- the resin material is at least one selected from the group consisting of acrylate resins, epoxy resins, olefin resins, polybenzoxazole resins, silicone resins and polyimide resins.
- a metal surface treatment method in which the surface treatment liquid according to [4] is brought into contact with a metal surface [13] The metal surface treatment method according to [12], wherein the metal is at least one selected from the group consisting of copper, aluminum, titanium, nickel, tin, iron, silver, gold, and alloys thereof. . [14] The metal surface treatment method according to [12], wherein the metal is copper or a copper alloy. [15] The metal surface treatment method according to [14], wherein an aqueous solution containing copper ions is brought into contact with the surface of the copper or copper alloy before the surface treatment liquid is brought into contact with the surface of copper or the copper alloy.
- a surface treatment method for an inorganic material wherein the surface treatment liquid according to [4] is brought into contact with the surface of the inorganic material.
- the ceramic is at least one selected from the group consisting of alumina, silicon carbide, aluminum nitride, silicon nitride, and barium titanate.
- a surface treatment method for a resin material wherein the surface treatment liquid according to [4] is brought into contact with the surface of the resin material.
- a method for adhering a metal and a resin material wherein the surface treatment liquid according to [4] is brought into contact with at least one of the metal and the resin material to form a chemical conversion film on at least one of the metal and the resin material.
- a method for adhering an inorganic material and a resin material, wherein the surface treatment liquid according to [4] is brought into contact with at least one of the inorganic material and the resin material to form a chemical conversion film on the at least one A method for bonding an inorganic material and a resin material, wherein the inorganic material and the resin material are bonded to each other through the chemical conversion film.
- a method for bonding a metal and an inorganic material, wherein the inorganic material is bonded to each other via the chemical conversion film.
- a printed wiring board in which two materials selected from the group consisting of a metal, an inorganic material, and a resin material are bonded through a chemical conversion film formed by the surface treatment liquid according to [4].
- a semiconductor wafer in which two materials selected from the group consisting of metals, inorganic materials, and resin materials are bonded via a chemical conversion film formed by the surface treatment liquid according to [4].
- An electronic device in which two materials selected from the group consisting of a metal, an inorganic material, and a resin material are bonded via a chemical conversion film formed by the surface treatment liquid according to [4].
- the resin material is at least one selected from the group consisting of acrylate resins, epoxy resins, olefin resins, benzoxazole resins, silicone resins, and polyimide resins.
- the inorganic material is at least one selected from the group consisting of silicon, ceramic and glass.
- the triazole silane compound of the present invention is a substance having a 1,2,4-triazole ring together with an alkoxysilyl group in the molecule. Therefore, by using this as a component, the function of preventing rust of the metal characteristic of the triazole compound And a silane coupling agent to which a function of curing an epoxy resin or a urethane resin is added. Moreover, according to the surface treatment liquid containing the triazolesilane compound of the present invention, it is possible to improve the adhesion between two different materials, that is, a metal and an inorganic material, a metal and a resin material, and an inorganic material and a resin material. it can.
- the triazole silane compound of the present invention is a triazole silane compound represented by the above chemical formula (I) (hereinafter sometimes referred to as triazole silane compound (I)), for example, 3-methyl-1- [2- (triethoxysilyl) ethyl] -1,2,4-triazole, 5-methyl-1- [4- (trimethoxysilyl) butyl] -1,2,4-triazole, 3-ethyl-1- [3- (trimethoxysilyl) propyl] -1,2,4-triazole, 3-propyl-1- [3- (trimethoxysilyl) propyl] -1,2,4-triazole, 3-isopropyl-1- [10- (trimethoxysilyl) decyl] -1,2,4-triazole, 3-butyl-1- [3- (trimethoxysilyl) propyl] -1,2,4-triazole, 3-hex
- the triazole silane compound of the present invention includes a triazole compound represented by the above chemical formula (II) (hereinafter sometimes referred to as triazole compound (II)) and a halogenated alkylsilane compound represented by the above chemical formula (III) (hereinafter referred to as “triazole compound”). And a halogenated alkylsilane compound (III)) in the presence of a dehydrohalogenating agent in an appropriate amount of a reaction solvent at an appropriate reaction temperature and reaction time. Can be synthesized (see Reaction Scheme (A)).
- triazole compound (II) 3-methyl-1,2,4-triazole, 3-ethyl-1,2,4-triazole, 3-propyl-1,2,4-triazole, 3-isopropyl-1,2,4-triazole, 3-butyl-1,2,4-triazole, 3-hexyl-1,2,4-triazole, 3-dodecyl-1,2,4-triazole, 3,5-dimethyl-1,2,4-triazole, 3,5-diisopropyl-1,2,4-triazole, 3-ethyl-5-octyl-1,2,4-triazole, 5-methyl-3-octyl-1,2,4-triazole, 3-phenyl-1,2,4-triazole, 3-methyl-5-phenyl-1,2,4-triazole, 3-ethyl-5-phenyl-1,2,4-triazole, 3,5-diphenyl-1,2,4-triazole, 3-benzyl-1,2,4-triazole, 5-propy
- halogenated alkylsilane compound (III) 1-chloromethyltrimethoxysilane, 1-chloromethyltriethoxysilane, 2-chloroethyltrimethoxysilane, 2-chloroethyltriethoxysilane, 3-chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 3-bromopropyltrimethoxysilane, 3-bromopropyltriethoxysilane, 3-iodopropyltrimethoxysilane, 3-iodopropyltriethoxysilane, 4-bromobutyltrimethoxysilane, 4-bromobutyltriethoxysilane, 5-bromopentyltrimethoxysilane, 5-bromopentyltriethoxysilane, 6-bromohexyltrimethoxysilane, 6-bromohexyltriethoxys
- the reaction solvent is not particularly limited as long as it is an inert solvent for the triazole compound (II) and the halogenated alkylsilane compound (III).
- a hydrocarbon solvent such as hexane, toluene, xylene
- Ether solvents such as diethyl ether, tetrahydrofuran, dioxane, cyclopentyl methyl ether
- Ester solvents such as ethyl acetate and butyl acetate
- Alcohol solvents such as methanol and ethanol
- Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone
- Ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone
- Acetonitrile, dimethyl sulfoxide, hexamethyl phosphoramide and the like can be mentioned.
- dehydrohalogenating agent examples include alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium methoxide, potassium t-butoxide; Alkali carbonates such as sodium carbonate, sodium bicarbonate, potassium bicarbonate; An organic base such as diazabicycloundecene, sodium hydride and the like can be mentioned.
- the reaction between the triazole compound (II) and the halogenated alkylsilane compound (III) proceeds stoichiometrically as shown in the above reaction scheme (A), but the amount of triazole compound (II) used (charged amount).
- the amount of use of the halogenated alkylsilane compound (III) with respect to () is 0.8, considering factors such as the reaction temperature and reaction time as well as the types of raw materials and reaction solvents used and the reaction scale. It is preferable that the ratio be in an appropriate range in the range of -1.2 times mole.
- the charged amount of the halogenated alkylsilane compound (III) is more than 1.2 times mol, the compound may be polymerized and gelled, and if less than 0.8 times mol, the purity of the product May decrease, and the product separation operation may become complicated.
- the dehydrohalogenating agent is used to neutralize hydrogen halide by-produced by the reaction between the triazole compound (II) and the halogenated alkylsilane compound (III). Should just be equimolar or more with respect to the usage-amount of halogenated alkylsilane compound (III).
- the reaction temperature is not particularly limited as long as the 1-position NH of the triazole compound (II) reacts with the halogenated alkylsilane compound (III), but is preferably in the range of 0 to 150 ° C. A range of ° C is more preferred.
- the reaction time is appropriately determined according to the set reaction temperature, but is preferably in the range of 30 minutes to 10 hours, and more preferably in the range of 1 to 8 hours.
- the silane coupling agent of the present invention contains a triazole silane compound represented by the above chemical formula (IV) (hereinafter sometimes referred to as triazole silane compound (IV)) as a component.
- the same surface treatment method as that of the conventional silane coupling agent can be employed.
- the surface treatment method include: (a) a method in which a treatment liquid obtained by diluting an appropriate amount of a silane coupling agent with an organic solvent is spray-coated on a substrate; and (b) the silane coupling agent with a water-organic solvent.
- a method of spray-applying a diluted treatment liquid onto a substrate (c) a method of spray-applying a treatment solution obtained by diluting the silane coupling agent with water, and (d) diluting the silane coupling agent with an organic solvent.
- a method of immersing the substrate in the treated liquid (e) a method of immersing the substrate in a treatment liquid obtained by diluting the silane coupling agent with a water-organic solvent, and (f) diluting the silane coupling agent with water.
- the method etc. which immerse a base material in a process liquid can be mentioned.
- organic solvent examples include hydrocarbon solvents such as benzene, toluene, xylene, heptane, hexane, cyclohexane, and n-octane; Halogenated hydrocarbon solvents such as dichloromethane, dichloroethane, carbon tetrachloride, chloroform, chlorobenzene, dichlorobenzene, trichlorobenzene; Ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone; Ether solvents such as diethyl ether, tetrahydrofuran, dioxane, ethylene glycol monomethyl ether (methyl cellosolve), ethylene glycol monoethyl ether (ethyl cellosolve), ethylene glycol monobutyl ether, diethylene glycol monobutyl ether; Examples thereof include alcohol solvents such as methanol, ethanol, 1-propanol, 2-
- Examples of the substrate used in the present invention include granular, needle-like, fiber-like, woven-like, plate-like, foil-like, and amorphous-like substrates formed from metals, inorganic materials, resin materials, and the like. be able to.
- the metal examples include copper, aluminum, titanium, nickel, tin, iron, silver, gold, and alloys thereof, and the base material is a plate, foil, or plating film made of these metals. Can do.
- Specific examples of the alloy are not particularly limited as long as the copper alloy is an alloy containing copper.
- Cu—Ag, Cu—Te, Cu—Mg, Cu—Sn, and Cu—Si are available.
- Other alloys include aluminum alloy (Al—Si alloy), nickel alloy (Ni—Cr alloy), iron alloy (Fe—Ni alloy, stainless steel, steel) and the like. Of these metals, copper and copper alloys are preferred.
- the inorganic material examples include silicon, ceramic, inorganic materials used as fillers, glass, and the like.
- silicon compounds such as silicon, silicon carbide, silica, glass, diatomaceous earth, calcium silicate, talc, glass beads, sericite activated clay, bentonite, aluminosilicate, mica, alumina, zinc oxide, iron oxide, oxidation Oxides such as magnesium, tin oxide and titanium oxide, hydroxides such as magnesium hydroxide, aluminum hydroxide and basic magnesium carbonate, carbonates such as calcium carbonate, zinc carbonate, hydrotalcite and magnesium carbonate, barium sulfate, Examples thereof include sulfates such as gypsum, titanates such as barium titanate, nitrides such as aluminum nitride and silicon nitride, and carbon fibers.
- silicon, ceramic alumina, silicon carbide, aluminum nitride, silicon nitride, barium titanate, etc.
- glass are examples of these inorganic materials
- nylon As the resin material, nylon, acrylate resin, epoxy resin, olefin resin, polybenzoxazole resin, silicone resin, polyimide resin, bismaleimide resin, maleimide resin, cyanate resin, polyphenylene ether resin, polyphenylene oxide resin, olefin resin, A fluorine-containing resin, a polyetherimide resin, a polyetheretherketone resin, a liquid crystal resin, and the like can be given. These may be mixed or modified to be combined with each other.
- acrylate resins, epoxy resins, olefin resins, polybenzoxazole resins, silicone resins and polyimide resins are preferable.
- the lipophilicity of the surface of the base material is increased, and the affinity (adhesiveness, adhesion) to the resin or the like can be improved.
- the surface treatment liquid of the present invention is a surface treatment liquid containing the triazolesilane compound (IV) described above, and this triazolesilane compound (IV) has the following chemical formula (I) and chemical formulas (IVa) to (IVc): The triazole silane compound shown by these is included.
- the triazole silane compound (I) is a triazole silane compound (trialkoxy compound) when n is 0 in the chemical formula (IV).
- the triazole silane compound represented by the chemical formula (IVa) (hereinafter sometimes referred to as triazole silane compound (IVa)) is a triazole silane compound when n is 1, and the triazole represented by the chemical formula (IVb).
- the silane compound (hereinafter sometimes referred to as triazole silane compound (IVb)) is a triazole silane compound when n is 2, and is represented by the chemical formula (IVc) (hereinafter referred to as triazole silane compound (IVc)). Is a triazole silane compound when n is 3.
- the triazole silane compounds (IVa) to (IVc) are species generated by hydrolysis of the triazole silane compound (I) present in the surface treatment liquid, and these are trialkoxy triazole silane compounds (I) In addition, it is suitable as a component of the silane coupling agent. Further, the triazolesilane compounds (IVa) to (IVc) can be used by being extracted from the surface treatment liquid by removing volatile components from the surface treatment liquid, for example.
- the triazolesilane compound (I) is used as a raw material when preparing the surface treatment liquid.
- Examples of the triazolesilane compound (I) are as described above.
- the surface treatment liquid of the present invention is prepared by mixing the triazole silane compound (I) with an organic solvent or triazole silane compound (I), a solubilizer and water.
- the solubilizer include acids, alkalis, and organic solvents. One of these solubilizers may be used alone, or two or more thereof may be used in combination.
- the solubilizer may be added after mixing the triazolesilane compound and water, or the triazolesilane compound, water, and water may be added.
- a mixed solution of solubilizers may be mixed, or water may be added after mixing the triazolesilane compound and the solubilizer.
- pure water such as ion-exchange water and distilled water, is preferable.
- Examples of the acid include mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, formic acid, acetic acid, propionic acid, butyric acid, 2-ethylbutyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid. , Lauric acid, myristic acid, palmitic acid, margaric acid, oleic acid, stearic acid, glycolic acid, lactic acid, gluconic acid, glyceric acid, malonic acid, succinic acid, levulinic acid, benzoic acid, oxalic acid, tartaric acid, malic acid, Examples include organic acids such as amino acids. These acids may be used alone or in combination of two or more.
- alkali examples include hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide, ammonia, methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, isopropylamine, butylamine, and pentyl.
- alkali metals such as sodium hydroxide and potassium hydroxide, ammonia, methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, isopropylamine, butylamine, and pentyl.
- organic solvent examples include methanol, ethanol, 1-propanol, 2-propanol, butanol, tert-butyl alcohol, ethylene glycol, propylene glycol, 1,4-butanediol, glycerin, diethylene glycol, triethylene glycol, and ethylene.
- Glycol monomethyl ether ethylene glycol dimethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol dimethyl ether, diethylene glycol mono Chill ether, diethylene glycol diethyl ether, diethylene glycol monobutyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether, tetrahydrofurfuryl alcohol, furfuryl alcohol, acetone, tetrahydrofuran, dioxane, acetonitrile, 2-pyrrolidone, formamide, dimethylformamide, dimethylacetamide, Examples include dimethyl sulfoxide, sulfolane, dimethyl carbonate, ethylene carbonate, N-methylpyrrolidon
- the content of the solubilizer is preferably 0.1 to 50% by weight in the surface treatment solution.
- the content of the solubilizer is more preferably 0.5% by weight or more in the surface treatment liquid, further preferably 1% by weight or more, more preferably 30% by weight or less, and 20% by weight. The following is more preferable.
- a substance having an alkoxysilyl group in the molecule acts as a silane coupling agent.
- the triazole silane compound used in the practice of the present invention has a triazole ring and an alkoxysilyl group (—Si—OR) in the molecule. Interacts with resin and copper to form chemical bonds.
- the alkoxysilyl group undergoes hydrolysis and is converted into a hydroxysilyl group (—Si—OH), and this hydroxysilyl group chemically bonds with copper oxide scattered on the surface of copper.
- a chemical film derived from the triazolesilane compound (IV) is formed on the surface of the copper by bonding with a triazole ring or a hydroxysilyl group.
- a resin layer made of a resin material is formed on the surface, the adhesion between copper and the resin material can be improved as compared with the case where the resin layer is formed directly on the copper surface.
- the concentration of the triazolesilane compound (IV) in the surface treatment liquid is 0.001 to 10% by weight in terms of the concentration of the trialkoxy triazolesilane compound (I). Preferably, it is 0.01 to 5% by weight.
- this concentration is less than 0.001% by weight, the effect of improving the adhesiveness is not sufficient, and when this concentration exceeds 10% by weight, the effect of improving the adhesiveness almost reaches its peak, and the triazolesilane compound It is not economical just because the amount of use increases.
- the triazolesilane compounds (IVa) to (IVc) having a hydroxysilyl group formed in the surface treatment liquid gradually react with each other to undergo dehydration condensation, and the hydroxysilyl group becomes a siloxane bond (Si—O—Si).
- Scheme (B) See scheme (B)) and converted into a silane oligomer (triazolesilane compound having a group represented by the chemical formula (e) in scheme (B)) that is hardly soluble in water.
- X of group shown by Chemical formula (e) is an integer showing the number of repeating units.
- the surface treatment liquid of the present invention is selected from the group consisting of acids, alkalis, and organic solvents as a solubilizer. It is preferable to contain at least one kind.
- halogen ions such as chlorine ions, bromine ions and iodine ions, and metal ions such as copper ions, iron ions and zinc ions in order to improve the stability of the surface treatment solution and the uniformity of the chemical conversion film.
- metal ions such as copper ions, iron ions and zinc ions in order to improve the stability of the surface treatment solution and the uniformity of the chemical conversion film.
- a known coupling agent may be used in combination as long as the effects of the present invention are not impaired.
- Known coupling agents include silane coupling agents having a thiol group (mercapto group), vinyl group, epoxy group, (meth) acryl group, amino group, chloropropyl group, and the like.
- silane coupling agents include: 3-mercaptopropyltrimethoxysilane, Mercaptosilane compounds such as 3-mercaptopropylmethyldimethoxysilane, Vinyltrichlorosilane, Vinyltrimethoxysilane, Vinylsilane compounds such as vinyltriethoxysilane, styrylsilane compounds such as p-styryltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, Epoxy silane compounds such as 3-glycidoxypropyltriethoxysilane, Acryloxysilane compounds such as 3-acryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyl
- the time (treatment time) for bringing the surface treatment liquid into contact with the substrate is preferably 1 second to 10 minutes, and more preferably 5 seconds to 3 minutes.
- the temperature of the treatment liquid when the surface treatment liquid is brought into contact with the substrate surface is preferably 5 to 50 ° C., but may be set as appropriate in relation to the treatment time.
- the substrate After bringing the surface treatment liquid of the present invention into contact with the substrate, the substrate may be washed with water and dried, or may be dried without washing with water. Drying is preferably performed at a temperature of room temperature to 150 ° C.
- the water used for washing is preferably pure water such as ion-exchanged water or distilled water, but the washing method and time are not particularly limited, and may be an appropriate time by means such as spraying or dipping.
- the surface of the chemical conversion film may be modified by performing treatments such as plasma, laser, ion beam, ozone, heating, and humidification on the chemical conversion film after drying.
- cleaning for the purpose of removing the resin / ion residue on the metal surface may be performed by using a mechanical polishing method such as plasma, laser, ion beam, permis brush, or a drilling method.
- the surface treatment solution of the present invention Before bringing the surface treatment solution of the present invention into contact with the surface of copper or a copper alloy (hereinafter sometimes referred to simply as copper), the surface of the copper is subjected to pickling treatment, alkali treatment, and roughening treatment. Further, at least one pretreatment selected from heat treatment, rust prevention treatment or chemical conversion treatment may be performed.
- the above pickling treatment is performed to remove oil and fat components adhering to the copper surface and to remove the oxide film on the copper surface.
- solutions such as hydrochloric acid solution, sulfuric acid solution, nitric acid solution, sulfuric acid-hydrogen peroxide solution, organic acid solution, inorganic acid-organic solvent solution, organic acid-organic solvent solution, etc. Can be used.
- the alkali treatment is performed to remove oil and fat components adhering to the copper surface and to remove residues from the previous step (for example, a dry film resist for forming a copper circuit).
- the alkali treatment includes alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, amines such as ammonia, ethanolamine, monopropanolamine, and tetramethylammonium hydroxide, sodium carbonate, sodium bicarbonate, and carbonate. Solutions such as aqueous solutions and organic solvent solutions containing potassium, potassium bicarbonate, ammonium carbonate, ammonium bicarbonate, sodium acetate, potassium acetate, sodium phosphate, disodium hydrogen phosphate, potassium phosphate, dipotassium hydrogen phosphate, etc. Can be used.
- the roughening treatment described above is performed in order to increase the adhesion between copper and the resin due to the anchor effect, and an uneven shape is imparted to the surface of the copper, thereby improving the adhesion between the copper and the resin material.
- methods such as a micro-etching method, electroplating method, electroless plating method, oxidation method (black oxide, brown oxide), oxidation / reduction method, brush polishing method, jet scrub method may be adopted. it can.
- microetching method for example, organic acid-cupric ion type, sulfuric acid-hydrogen peroxide type, persulfate type, copper chloride type, and iron chloride type etching agents can be used.
- electroplating method fine copper particles are deposited on the copper surface to form irregularities on the copper surface.
- At least one film selected from nickel, nickel-phosphorus, zinc, zinc-nickel, copper-zinc, copper-nickel, copper-nickel-cobalt, or nickel-cobalt is formed on the copper surface. Is formed.
- This film can be formed by employing a known electroplating method, but is not limited to electroplating, and vapor deposition or other means may be used.
- the above rust prevention treatment is to prevent the copper surface from being oxidized and corroded, and a method of forming a zinc or zinc alloy composition plating film or electrolytic chromate plating film on the copper surface. Can be adopted. Further, a treatment liquid containing an organic compound rust inhibitor such as a benzotriazole rust inhibitor may be brought into contact with the copper surface.
- a method of forming a passive film of tin or a method of forming a passive film of copper oxide can be employed.
- an aqueous solution containing copper ions Before bringing the surface treatment liquid of the present invention into contact with the copper surface, an aqueous solution containing copper ions may be brought into contact with the copper surface.
- This aqueous solution containing copper ions has a function of making the thickness of the chemical conversion film formed on the surface of copper uniform.
- the copper ion source of the aqueous solution containing copper ions is not particularly limited as long as it is a copper salt that dissolves in water, and examples thereof include copper salts such as copper sulfate, copper nitrate, copper chloride, copper formate, and copper acetate. In order to solubilize the copper salt in water, ammonia or hydrochloric acid may be added.
- an acidic aqueous solution or an alkaline aqueous solution may be brought into contact with the copper surface.
- This acidic aqueous solution or alkaline aqueous solution also has a function of making the thickness of the chemical conversion film formed on the surface of copper uniform, similarly to the aqueous solution containing copper ions.
- the acidic aqueous solution and the alkaline aqueous solution are not particularly limited.
- Examples of the acidic aqueous solution include an aqueous solution containing a mineral acid such as sulfuric acid, nitric acid and hydrochloric acid, and an aqueous solution containing an organic acid such as formic acid, acetic acid, lactic acid, glycolic acid and amino acid.
- Examples of the alkaline aqueous solution include hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide, amines such as ammonia, ethanolamine, monopropanolamine, and tetramethylammonium hydroxide, sodium carbonate, sodium bicarbonate, and potassium carbonate.
- an aqueous solution containing potassium hydrogen carbonate, ammonium carbonate, ammonium hydrogen carbonate, sodium acetate, potassium acetate, sodium phosphate, disodium hydrogen phosphate, potassium phosphate, dipotassium hydrogen phosphate and the like containing potassium hydrogen carbonate, ammonium carbonate, ammonium hydrogen carbonate, sodium acetate, potassium acetate, sodium phosphate, disodium hydrogen phosphate, potassium phosphate, dipotassium hydrogen phosphate and the like.
- an aqueous solution containing a known coupling agent may be brought into contact with the copper surface.
- an aqueous solution containing a known coupling agent may be brought into contact with the copper surface.
- a treatment liquid containing a known organic compound rust inhibitor such as a benzotriazole rust inhibitor may be contacted.
- the surface treatment liquid of the present invention can be used to treat the surface of at least one substrate selected from the group consisting of the aforementioned metals, inorganic materials, and resin materials.
- a chemical conversion film can be formed on the surface of the base material, and adhesion with other materials can be enhanced.
- two materials selected from the group consisting of the above metals, inorganic materials, and resin materials can be bonded using the surface treatment liquid of the present invention.
- the affinity between each other can be improved, so even different materials can be made stronger. Can be glued.
- Adhesion method As a bonding method, a known method can be used.
- the surface treatment liquid of the present invention is brought into contact with the surface of a base material made of a metal, an inorganic material or a resin material to form a chemical conversion film, and another base material is applied, pressed or mixed to a part or all of the formed chemical conversion film. And the like, use of an adhesive, an adhesive sheet (film), or a combination of these means.
- the surface treatment liquid of this invention is made to contact the surface of two base materials selected from a metal, an inorganic material, and a resin material, a chemical conversion film is formed on the surface of two base materials, respectively, and two base materials
- a chemical conversion film is formed on the surface of two base materials, respectively, and two base materials
- examples of such means include application, pressure bonding, and mixing, and the use of an adhesive, an adhesive sheet (film), or a combination of these means.
- the surface treatment liquid of the present invention it is possible to bond two materials, particularly two materials different from each other as described above, so that various electronic / electronic components, semiconductor wafers, printed wiring boards, and other electronic devices Can be suitably used.
- the surface treatment liquid of the present invention can be suitably used for a substrate formed of a metal, particularly copper or a copper alloy.
- a substrate formed of a metal particularly copper or a copper alloy.
- a metal particularly copper or a copper alloy.
- insulating resin layer In a printed wiring board having an insulating resin layer in contact with the copper wiring layer, the adhesion between the copper wiring layer and the insulating resin layer can be improved.
- an object is to improve adhesion (adhesion) between a semiconductor circuit formed on the semiconductor wafer and a protective film, for example, an insulating protective film such as a buffer coat or a bump protective film.
- a protective film for example, an insulating protective film such as a buffer coat or a bump protective film.
- a protective film for example, an insulating protective film such as a buffer coat or a bump protective film.
- a protective film for example, an insulating protective film such as a buffer coat or a bump protective film.
- a protective film for example, an insulating protective film such as a buffer coat or a bump protective film.
- a protective film for example, an insulating protective film such as a buffer coat or a bump protective film.
- a protective film for example, an insulating protective film such as a buffer coat or a bump protective film.
- a copper circuit redistribution layer intended to improve the adhesion (adhesion) between the copper circuit redistribution layer
- the printed wiring board can be produced by bringing the surface treatment liquid of the present invention and the surface of the copper wiring into contact with each other, then washing and drying, and then forming an insulating resin layer on the surface of the copper wiring.
- the contact method is as described above, and it is preferable that immersion of the copper wiring in the surface treatment liquid or spraying of the copper wiring with the treatment liquid is simple and reliable.
- limiting in particular also about the method of the said water washing but the immersion to the copper wiring in washing
- a known method such as a method of attaching a semi-cured resin material or a means of applying a liquid resin material containing a solvent can be employed.
- a via hole is formed to connect the upper and lower wirings.
- a first conductive layer is formed on the first surface of the insulating substrate or the insulating substrate having through-hole through holes and via holes, the second surface opposite to the first surface, and the inner walls of the through-hole through holes and via holes.
- a photocrosslinkable resin layer and a mask layer are formed on the first surface and the second surface, and the first conductive layer of the first surface and the second surface, the through-hole through hole and the via hole inner wall is formed as a photocrosslinkable resin.
- Covering with a layer and a mask layer (C) pattern exposing the photocrosslinkable resin layer around the first and second surfaces and the through-hole through-holes and via-holes; (D) removing the mask layer around the first and second surfaces and the through-hole through-holes and via-holes; (E) Using the photocrosslinkable resin layer removing liquid, the first and second surfaces, and the uncured photocrosslinkable resin layer around the through-hole through hole and via hole are developed and removed, and the first surface is removed.
- a circuit board including at least one step of laminating an insulating resin layer on the first surface, the second surface, and the first, second, and third conductive layers of the through hole through hole and the inner wall of the via hole.
- the surface treatment liquid of the present invention is brought into contact with at least one metal layer or resist layer of the crosslinkable resin layer and the insulating resin laminate to produce a printed wiring board.
- a first conductive layer is formed on the first surface of the insulating substrate or the insulating substrate having through-hole through holes and via holes, the second surface opposite to the first surface, and the inner walls of the through-hole through holes and via holes.
- a photocrosslinkable resin layer and a mask layer are formed on the first surface and the second surface, and the first conductive layer of the first surface and the second surface, the through-hole through hole and the via hole inner wall is formed as a photocrosslinkable resin.
- Covering with a layer and a mask layer (C) pattern exposing the photocrosslinkable resin layer around the first and second surfaces and the through-hole through-holes and via-holes; (D) removing the mask layer around the first and second surfaces and the through-hole through-holes and via-holes; (E) Using the photocrosslinkable resin layer removing liquid, the first and second surfaces, and the uncured photocrosslinkable resin layer around the through-hole through hole and via hole are developed and removed, and the first surface is removed.
- a circuit board including at least one step of laminating an insulating resin layer on the first surface, the second surface, and the first, second, and third conductive layers of the through hole through hole and the inner wall of the via hole.
- the surface treatment liquid of the present invention is brought into contact with at least one metal layer or resist layer of the crosslinkable resin layer and the insulating resin laminate to produce a printed wiring board.
- the copper wiring and conductive layer may be prepared by any method such as electroless plating, electrolytic plating, vapor deposition, sputtering, damascene, inner via holes, through holes, connection terminals, etc. It may be included.
- “copper” according to the present invention is a foil (electrolytic copper foil, rolled copper foil, copper foil with resin, copper foil with carrier) used for electronic devices such as printed wiring boards and lead frames, ornaments, building materials, etc. , Electroless copper foil, sputtered copper foil, thin copper foil), plating film (electroless copper plating film, electrolytic copper plating film), thin film, grains, needles, It is used in applications and forms such as fibers, wires, rods, pipes, and plates.
- the copper surface is preferably a smooth surface having an average roughness of 0.1 ⁇ m or less.
- the copper surface may be plated with nickel, zinc, chromium, tin or the like as a pretreatment.
- the copper foil with a carrier treated with the surface treatment liquid of the present invention is a printed wiring including a step of forming a circuit by any of a semi-additive method, a subtractive method, a partial additive method, or a modified semi-additive method.
- An ultra-thin electrolytic copper foil used for a plate comprising a copper foil carrier, a release layer laminated on the copper foil carrier, and an ultra-thin copper layer laminated on the release layer.
- the copper surface may be subjected to at least one pretreatment selected from the group consisting of pickling treatment, roughening treatment, heat resistance treatment, rust prevention treatment or chemical conversion treatment.
- An insulating composition can be obtained by incorporating the silane coupling agent of the present invention into a resin material or an inorganic material. Moreover, an insulating composition can also be obtained by dissolving the triazole silane compound (IV) in an organic solvent or the like and mixing it with a resin material or an inorganic material.
- the content of the triazolesilane compound (IV) in the insulating composition is preferably 0.001 to 10% by weight, and more preferably 0.01 to 5% by weight.
- the insulating composition can be produced by a known method.
- the insulating composition can be produced by dissolving the triazole silane compound (IV) in an organic solvent and mixing it with a solid or liquid resin material. Further, the triazolesilane compound (IV) may be directly added to the liquid resin material and mixed to produce an insulating composition.
- the insulating composition of the present invention provides an insulating material having high adhesive strength, it can be suitably used for various electric / electronic components and electronic devices such as printed wiring boards.
- Japanese Patent Application Laid-Open No. 2009-19266 discloses a step of applying a liquid containing a silane coupling agent to a metal surface and the metal surface to which the liquid is applied at a temperature of 25 to 150 ° C. and within 5 minutes.
- the invention relates to a method for forming a silane coupling agent film, characterized by comprising a step of performing drying at a step and a step of washing the dried metal surface with water.
- an adhesive metal layer such as tin may be formed on the metal surface in advance by immersion plating as a surface treatment.
- the surface treatment liquid of the present invention can be used as a liquid containing the silane coupling agent.
- the matter described in this patent gazette shall constitute a part of this specification by reference.
- the triazole silane compounds used in Comparative Example 1 are as follows. [Triazole silane compound] 1- [3- (trimethoxysilyl) propyl] -1,2,4-triazole: synthesized according to the method described in Patent Document 2.
- test piece Electrolytic copper foil (thickness: 35 ⁇ m) was used as a test piece.
- Treatment of test piece The test pieces were processed according to the following steps a and b. a. Acid cleaning / 1 minute (room temperature), water washing, drying / 1 minute (100 ° C) b.
- Example 1 ⁇ Synthesis of 3,5-diamino-1- [3- (trimethoxysilyl) propyl] -1,2,4-triazole> To a suspension consisting of 15.0 g (0.151 mol) of 3,5-diamino-1,2,4-triazole and 100 mL of dehydrated N, N-dimethylformamide, 29.2 g of a 28% sodium methoxide methanol solution at room temperature. (0.151 mol) was added and stirred as a homogeneous solution for 30 minutes, and then 30.1 g (0.151 mol) of 3-chloropropyltrimethoxysilane was added, followed by stirring at 77-80 ° C. for 4 hours.
- the 1 H-NMR spectrum data of the obtained viscous product was as follows. 1 H-NMR (DMSO-d 6 ) ⁇ : 0.51 (t, 2H), 1.62 (m, 2H), 3.46 (s, 9H), 3.58 (t, 2H), 4.69 (s, 2H), 5.11 (s , 2H). From the 1 H-NMR spectrum data, the obtained viscous product was identified as the title triazolesilane compound represented by the chemical formula (V).
- the 1 H-NMR spectrum data of the obtained viscous product was as follows. 1 H-NMR (DMSO-d 6 ) ⁇ : 0.49 (t, 2H), 1.14 (t, 9H), 1.62 (m, 2H), 3.56 (t, 2H), 3.73 (q, 6H), 4.67 (s , 2H), 5.11 (s, 2H). From the 1 H-NMR spectrum data, the obtained viscous product was identified as the title triazolesilane compound represented by the chemical formula (VI).
- the 1 H-NMR spectrum data of the obtained liquid was as follows. 1 H-NMR (DMSO-d 6 ) ⁇ : 0.54 (t, 2H), 1.76 (m, 2H), 2.15 (s, 3H), 2.31 (s, 3H), 3.47 (s, 9H), 3.94 (t , 2H). From the 1 H-NMR spectrum data, the obtained liquid was identified as the title triazolesilane compound represented by the chemical formula (VII).
- the 1 H-NMR spectrum data of the obtained liquid was as follows. 1 H-NMR (DMSO-d 6 ) ⁇ : 0.58 (t, 2H), 1.90 (m, 2H), 3.48 (s, 9H), 4.20 (t, 2H), 7.41-7.48 (m, 2H), 8.01 -8.05 (m, 3H), 8.67 (s, 1H). From the 1 H-NMR spectrum data, the obtained liquid was identified as the title triazolesilane compound represented by the chemical formula (VIII).
- the 1 H-NMR spectrum data of the obtained liquid was as follows. 1 H-NMR (DMSO-d 6 ) ⁇ : 0.54 (t, 2H), 1.70 (m, 2H), 2.38 (s, 3H), 3.47 (s, 9H), 3.75 (t, 2H). From the 1 H-NMR spectrum data, the obtained liquid was identified as the title triazolesilane compound represented by the chemical formula (IX).
- the 1 H-NMR spectrum data of the obtained liquid was as follows. 1 H-NMR (DMSO-d 6 ) ⁇ : 0.52 (m, 2H), 0.85 (br s, 3H), 1.1-1.3 (br s, 10H), 1.58 (br s, 2H), 1.75 (m, 2H ), 2.16 (s, 3H), 2.62 (t, 2H), 3.46 (s, 9H), 3.94 (t, 2H). From the 1 H-NMR spectrum data, the obtained liquid was identified as the title triazolesilane compound represented by the chemical formula (X).
- the 1 H-NMR spectrum data of the obtained liquid was as follows. 1 H-NMR (CDCl 3 ) ⁇ : 0.61 (t, 2H), 1.22 (t, 9H), 1.2-1.4 (m, 6H), 1.62 (m, 2H), 3.42 (t, 2H), 3.48 (q , 6H), 7.64 (s, 1H). From the 1 H-NMR spectrum data, the obtained liquid was identified as the title triazolesilane compound represented by the chemical formula (XI).
- the 1 H-NMR spectrum data of the obtained liquid was as follows. 1 H-NMR (DMSO-d 6 ) ⁇ : 0.51 (t, 2H), 1.73 (m, 2H), 3.46 (s, 9H), 3.86 (t, 2H), 5.21 (s, 2H), 7.91 (s , 1H). From the 1 H-NMR spectrum data, the obtained liquid was identified as the title triazolesilane compound represented by the chemical formula (XII).
- Example 9 A copper surface treatment solution was prepared using the triazolesilane compound synthesized in Example 1 as a silane coupling agent component. That is, 200 g of ethylene glycol monobutyl ether was added to 10 g of the triazolesilane compound, followed by addition of 790 g of water, followed by stirring at room temperature for 2 hours to prepare a copper surface treatment liquid (hereinafter referred to as treatment liquid A). About this processing liquid A, it confirmed that the trimethoxysilyl group of the said triazole silane compound was hydrolyzed to the trihydroxysilyl group, and performed the adhesiveness test. The test results obtained were as shown in Table 1.
- Example 10 to 16 In the same manner as in Example 9, instead of the triazole silane compound synthesized in Example 1, using the triazole silane compound synthesized in Examples 2 to 8, a copper surface treatment liquid (hereinafter, treatment liquid B, C, D, E, F, G, and H) were prepared. After confirming that the trimethoxysilyl group or triethoxysilyl group of the triazolesilane compound in these treatment solutions was hydrolyzed to the trihydroxysilyl group, an adhesion test was conducted. The test results obtained were as shown in Table 1.
- treatment liquid B, C, D, E, F, G, and H a copper surface treatment liquid
- Example 1 In the same manner as in Example 9, instead of the triazolesilane compound synthesized in Example 1, 1- [3- (trimethoxysilyl) propyl] -1,2,4-triazole was used to treat the surface of copper. A liquid (hereinafter referred to as treatment liquid I) was prepared. About this process liquid I, it confirmed that the trimethoxysilyl group of the said triazole silane compound was hydrolyzed to the trihydroxysilyl group, and performed the adhesiveness test. The test results obtained were as shown in Table 1.
- treatment liquid J A copper surface treatment liquid (hereinafter referred to as treatment liquid J) having the same composition as the treatment liquid A was prepared except that no silane coupling agent component was used, and an adhesion test was performed. The test results obtained were as shown in Table 1.
- the surface of copper using the triazolesilane compound of the present invention having a substituent at the 3-position and / or 5-position of the 1,2,4-triazole ring as a silane coupling agent component It is recognized that the treatment liquid exhibits an excellent effect of increasing the adhesive force between copper and resin.
- the effect of increasing the adhesive force between copper and resin is remarkable, and in particular, in the case of a triazole silane compound having two amino groups, the above-mentioned adhesive force Is dramatically improved.
- the triazole silane compound of the present invention can be used as a silane coupling agent having a function of preventing rust of the metal, which is a characteristic of the triazole compound, and a function of curing an epoxy resin or a urethane resin, there are different types of materials. It is expected to be used for composite materials such as printed wiring boards produced by combining many.
- the adhesion (adhesion) of the metal, the inorganic material, and the resin material can be sufficiently ensured, so that the surface of the base material can be maintained in a smooth state without being roughened. Therefore, the present invention can greatly contribute to the realization of the multilayer printed wiring board, such as miniaturization, thinning, high frequency, high density, etc., and thus the industrial applicability is great.
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Abstract
Description
特許文献2には、アルミニウムおよびマグネシウム合金の腐食抑制剤に使用されるシラン化合物として、1N-トリメトキシシリルプロピル-1,2,4-トリアゾールが提案されている。
また、当該トリアゾールシラン化合物を用いた表面処理液、表面処理方法および異なる材料の接着方法を提供することを目的とする。
〔1〕化学式(I)で示されるトリアゾールシラン化合物。
〔6〕金属、無機材料および樹脂材料からなる群から選択される2つの材料を接着するために用いる前記〔4〕に記載の表面処理液。
〔7〕前記金属が、銅、アルミニウム、チタン、ニッケル、錫、鉄、銀、金およびこれらの合金からなる群から選択される少なくとも1つである前記〔5〕または〔6〕に記載の表面処理液。
〔8〕前記金属が銅または銅合金である前記〔5〕または〔6〕に記載の表面処理液。
〔9〕前記無機材料が、シリコン、セラミックおよびガラスからなる群から選択される少なくとも1つである前記〔5〕または〔6〕に記載の表面処理液。
〔10〕前記セラミックが、アルミナ、炭化ケイ素、窒化アルミ、窒化ケイ素およびチタン酸バリウムからなる群から選択される少なくとも1つである前記〔9〕に記載の表面処理液。
〔11〕前記樹脂材料が、アクリレート樹脂、エポキシ樹脂、オレフィン樹脂、ポリベンゾオキサゾール樹脂、シリコーン樹脂およびポリイミド樹脂からなる群から選択される少なくとも1つである前記〔5〕または〔6〕に記載の表面処理液。
〔13〕前記金属が、銅、アルミニウム、チタン、ニッケル、錫、鉄、銀、金およびこれらの合金からなる群から選択される少なくとも1つである前記〔12〕に記載の金属の表面処理方法。
〔14〕前記金属が、銅または銅合金である前記〔12〕に記載の金属の表面処理方法。
〔15〕前記表面処理液を銅または銅合金の表面に接触させる前に、銅イオンを含む水溶液を前記銅または銅合金の表面に接触させる前記〔14〕に記載の金属の表面処理方法。
〔16〕前記表面処理液を銅または銅合金の表面に接触させた後に、酸性水溶液またはアルカリ性水溶液を前記銅または銅合金の表面に接触させる前記〔14〕または〔15〕に記載の金属の表面処理方法。
〔18〕前記無機材料が、シリコン、セラミックおよびガラスからなる群から選択される少なくとも1つである前記〔17〕に記載の無機材料の表面処理方法。
〔19〕前記セラミックが、アルミナ、炭化ケイ素、窒化アルミ、窒化ケイ素およびチタン酸バリウムからなる群から選択される少なくとも1つである前記〔18〕に記載の無機材料の表面処理方法。
〔21〕前記樹脂材料が、アクリレート樹脂、エポキシ樹脂、オレフィン樹脂、ポリベンゾオキサゾール樹脂、シリコーン樹脂およびポリイミド樹脂からなる群から選択される少なくとも1つである前記〔20〕に記載の樹脂材料の表面処理方法。
〔23〕無機材料と樹脂材料の接着方法であって、前記〔4〕に記載の表面処理液を、無機材料および樹脂材料の少なくとも一方に接触させて当該少なくとも一方に化成皮膜を形成し、前記無機材料と前記樹脂材料とを前記化成皮膜を介して互いに接着する無機材料と樹脂材料の接着方法。
〔24〕金属と無機材料の接着方法であって、前記〔4〕に記載の表面処理液を、金属および無機材料の少なくとも一方に接触させて当該少なくとも一方に化成皮膜を形成し、前記金属と前記無機材料とを前記化成皮膜を介して互いに接着する金属と無機材料の接着方法。
〔26〕金属、無機材料および樹脂材料からなる群から選択される2つの材料を、前記〔4〕に記載の表面処理液により形成された化成皮膜を介して接着した半導体ウェハ。
〔27〕金属、無機材料および樹脂材料からなる群から選択される2つの材料を、前記〔4〕に記載の表面処理液により形成された化成皮膜を介して接着した電子デバイス。
〔29〕前記樹脂材料が、アクリレート樹脂、エポキシ樹脂、オレフィン樹脂、ベンゾオキサゾール樹脂、シリコーン樹脂およびポリイミド樹脂からなる群から選択される少なくとも1つである前記〔28〕に記載の絶縁性組成物。
〔30〕前記無機材料が、シリコン、セラミックおよびガラスからなる群から選択される少なくとも1つである前記〔28〕に記載の絶縁性組成物。
〔32〕前記〔28〕~〔30〕のいずれか一つに記載の絶縁性組成物から得られる絶縁層を有するプリント配線板。
〔33〕前記〔28〕~〔30〕のいずれか一つに記載の絶縁性組成物から得られる絶縁層を有する半導体ウェハ。
〔34〕前記〔28〕~〔30〕のいずれか一つに記載の絶縁性組成物から得られる絶縁層を有する電子デバイス。
また、本発明のトリアゾールシラン化合物を含有した表面処理液によれば、材質の異なる2つの材料、即ち、金属と無機材料、金属と樹脂材料および、無機材料と樹脂材料の接着性を高めることができる。
本発明のトリアゾールシラン化合物は、前記の化学式(I)で示されるトリアゾールシラン化合物(以下、トリアゾールシラン化合物(I)ということがある)であり、例えば、
3-メチル-1-[2-(トリエトキシシリル)エチル]-1,2,4-トリアゾール、
5-メチル-1-[4-(トリメトキシシリル)ブチル]-1,2,4-トリアゾール、
3-エチル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-プロピル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-イソプロピル-1-[10-(トリメトキシシリル)デシル]-1,2,4-トリアゾール、
3-ブチル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-ヘキシル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
5-メチル-3-オクチル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-ドデシル-1-[6-(トリエトキシシリル)ヘキシル]-1,2,4-トリアゾール、
3,5-ジメチル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3,5-ジイソプロピル-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
3-フェニル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-メチル-5-フェニル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-エチル-5-フェニル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3,5-ジフェニル-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
3-ベンジル-1-[4-(トリエトキシシリル)ブチル]-1,2,4-トリアゾール、
3-ベンジル-5-フェニル-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
3-ヘキシルチオ-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
5-プロピル-3-ベンジル-1-[6-(トリエトキシシリル)ヘキシル]-1,2,4-トリアゾール、
3-アミノ-1-(トリエトキシシリル)メチル-1,2,4-トリアゾール、
3-アミノ-1-[2-(トリメトキシシリル)エチル]-1,2,4-トリアゾール、
3-アミノ-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
5-アミノ-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
5-アミノ-3-エチル-1-[6-(トリメトキシシリル)ヘキシル]-1,2,4-トリアゾール、
3-アミノ-5-フェニル-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
3-アミノ-5-ベンジル-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
3-アミノ-1-[6-(トリメトキシシリル)ヘキシル]-1,2,4-トリアゾール、
3-アミノ-1-[6-(トリエトキシシリル)ヘキシル]-1,2,4-トリアゾール、
3-アミノ-1-[12-(トリメトキシシリル)ドデシル]-1,2,4-トリアゾール、
3,5-ジアミノ-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3,5-ジアミノ-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
3,5-ジアミノ-1-[6-(トリメトキシシリル)ヘキシル]-1,2,4-トリアゾール、
3,5-ジアミノ-1-[12-(トリメトキシシリル)ドデシル]-1,2,4-トリアゾール、
3-メチルチオ-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-イソプロピルチオ-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-ヘキシルチオ-1-[10-(トリエトキシシリル)デシル]-1,2,4-トリアゾール、
3-エチルチオ-5-イソプロピル-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
3,5-ビス(メチルチオ)-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-メチルチオ-5-ヘキシルチオ-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
3-アミノ-5-メチルチオ-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
5-アミノ-3-メチルチオ-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール、
5-アミノ-3-メチルチオ-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール、
5-アミノ-3-イソプロピルチオ-1-[6-(トリエトキシシリル)ヘキシル]-1,2,4-トリアゾール、
3-アミノ-5-ヘキシルチオ-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾール等が挙げられる。
3-メチル-1,2,4-トリアゾール、
3-エチル-1,2,4-トリアゾール、
3-プロピル-1,2,4-トリアゾール、
3-イソプロピル-1,2,4-トリアゾール、
3-ブチル-1,2,4-トリアゾール、
3-ヘキシル-1,2,4-トリアゾール、
3-ドデシル-1,2,4-トリアゾール、
3,5-ジメチル-1,2,4-トリアゾール、
3,5-ジイソプロピル-1,2,4-トリアゾール、
3-エチル-5-オクチル-1,2,4-トリアゾール、
5-メチル-3-オクチル-1,2,4-トリアゾール、
3-フェニル-1,2,4-トリアゾール、
3-メチル-5-フェニル-1,2,4-トリアゾール、
3-エチル-5-フェニル-1,2,4-トリアゾール、
3,5-ジフェニル-1,2,4-トリアゾール、
3-ベンジル-1,2,4-トリアゾール、
5-プロピル-3-ベンジル-1,2,4-トリアゾール、
3-ベンジル-5-フェニル-1,2,4-トリアゾール、
3-アミノ-1,2,4-トリアゾール、
3-アミノ-5-エチル-1,2,4-トリアゾール、
3-アミノ-5-フェニル-1,2,4-トリアゾール、
3-アミノ-5-ベンジル-1,2,4-トリアゾール、
3,5-ジアミノ-1,2,4-トリアゾール、
3-メチルチオ-1,2,4-トリアゾール、
3-エチルチオ-5-イソプロピル-1,2,4-トリアゾール、
3-イソプロピルチオ-1,2,4-トリアゾール、
3-ヘキシルチオ-1,2,4-トリアゾール、
3,5-ビス(メチルチオ)-1,2,4-トリアゾール、
3-メチルチオ-5-ヘキシルチオ-1,2,4-トリアゾール、
3-アミノ-5-メチルチオ-1,2,4-トリアゾール、
3-アミノ-5-イソプロピルチオ-1,2,4-トリアゾール及び
3-アミノ-5-ヘキシルチオ-1,2,4-トリアゾール等が挙げられる。
1-クロロメチルトリメトキシシラン、
1-クロロメチルトリエトキシシラン、
2-クロロエチルトリメトキシシラン、
2-クロロエチルトリエトキシシラン、
3-クロロプロピルトリメトキシシラン、
3-クロロプロピルトリエトキシシラン、
3-ブロモプロピルトリメトキシシラン、
3-ブロモプロピルトリエトキシシラン、
3-ヨードプロピルトリメトキシシラン、
3-ヨードプロピルトリエトキシシラン、
4-ブロモブチルトリメトキシシラン、
4-ブロモブチルトリエトキシシラン、
5-ブロモペンチルトリメトキシシラン、
5-ブロモペンチルトリエトキシシラン、
6-ブロモヘキシルトリメトキシシラン、
6-ブロモヘキシルトリエトキシシラン、
8-ブロモオクチルトリメトキシシラン、
8-ブロモオクチルトリエトキシシラン、
10-ブロモデシルトリメトキシシラン、
10-ブロモデシルトリエトキシシラン、
12-ブロモドデシルトリメトキシシラン及び
12-ブロモドデシルトリエトキシシラン等が挙げられる。
ジエチルエーテル、テトラヒドロフラン、ジオキサン、シクロペンチルメチルエーテル等のエーテル系溶剤;
酢酸エチル、酢酸ブチル等のエステル系溶剤;
メタノール、エタノール等のアルコール系溶剤;
N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン等のアミド系溶剤;
アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系溶剤;
アセトニトリル、ジメチルスルホキシドやヘキサメチルホスホロアミド等を挙げることができる。
炭酸ナトリウム、炭酸水素ナトリウム、炭酸水素カリウム等の炭酸アルカリ塩;
ジアザビシクロウンデセン等の有機塩基や水素化ナトリウム等を挙げることができる。
ハロゲン化アルキルシラン化合物(III)の仕込み量が1.2倍モルよりも多いと、該化合物が重合してゲル化する惧れがあり、0.8倍モルよりも少ないと、生成物の純度が低下したり、生成物の分離操作が煩雑になる等の惧れがある。
また、脱ハロゲン化水素剤は、トリアゾール化合物(II)とハロゲン化アルキルシラン化合物(III)の反応により副生するハロゲン化水素を中和する為に使用されるので、その使用量(仕込量)は、ハロゲン化アルキルシラン化合物(III)の使用量に対して等モル以上であればよい。
本発明のシランカップリング剤は、前記の化学式(IV)で示されるトリアゾールシラン化合物(以下、トリアゾールシラン化合物(IV)ということがある)を成分とする。
この表面処理方法としては、例えば、(a)適宜量のシランカップリング剤を有機溶剤により希釈した処理液を基材にスプレー塗布する方法、(b)同シランカップリング剤を水-有機溶剤により希釈した処理液を基材にスプレー塗布する方法、(c)同シランカップリング剤を水により希釈した処理液を基材にスプレー塗布する方法、(d)同シランカップリング剤を有機溶剤により希釈した処理液に基材を浸漬する方法、(e)同シランカップリング剤を水-有機溶剤により希釈した処理液に基材を浸漬する方法、(f)同シランカップリング剤を水により希釈した処理液に基材を浸漬する方法等を挙げることができる。
ジクロロメタン、ジクロロエタン、四塩化炭素、クロロホルム、クロロベンゼン、ジクロロベンゼン、トリクロロベンゼン等のハロゲン化炭化水素系溶剤;
アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン系溶剤;
ジエチルエーテル、テトラヒドロフラン、ジオキサン、エチレングリコールモノメチルエーテル(メチルセロソルブ)、エチレングリコールモノエチルエーテル(エチルセロソルブ)、エチレングリコールモノブチルエーテル、ジエチレングリコールモノブチルエーテル等のエーテル系溶剤;
メタノール、エタノール、1-プロパノール、2-プロパノール、n-ブチルアルコール、2-ブチルアルコール、tert-ブチルアルコール、エチレングリコール、ジエチレングリコール、プロピレングリコール等のアルコール系溶剤などを挙げることができる。
前記合金の具体例としては、銅合金では、銅を含む合金であれば特に限定されず、例えば、Cu-Ag系、Cu-Te系、Cu-Mg系、Cu-Sn系、Cu-Si系、Cu-Mn系、Cu-Be-Co系、Cu-Ti系、Cu-Ni-Si系、Cu-Zn-Ni系、Cu-Cr系、Cu-Zr系、Cu-Fe系、Cu-Al系、Cu-Zn系、Cu-Co系等の合金が挙げられる。
また、その他の合金では、アルミニウム合金(Al-Si合金)、ニッケル合金(Ni-Cr合金)、鉄合金(Fe-Ni合金、ステンレス、鋼)等が挙げられる。
これらの金属の中では、銅および銅合金が好ましい。
具体的には、シリコン、炭化ケイ素、シリカ、ガラス、珪藻土、珪酸カルシウム、タルク、硝子ビーズ、セリサイト活性白土、ベントナイト、アルミノケイ酸塩、マイカ等のケイ素化合物、アルミナ、酸化亜鉛、酸化鉄、酸化マグネシウム、酸化錫、酸化チタン等の酸化物、水酸化マグネシウム、水酸化アルミニウム、塩基性炭酸マグネシウム等の水酸化物、炭酸カルシウム、炭酸亜鉛、ハイドロタルサイト、炭酸マグネシウム等の炭酸塩、硫酸バリウム、石膏等の硫酸塩、チタン酸バリウム等のチタン酸塩、窒化アルミ、窒化ケイ素等の窒化物、炭素繊維等が挙げられる。
これらの無機材料の中では、シリコン、セラミック(アルミナ、炭化ケイ素、窒化アルミ、窒化ケイ素およびチタン酸バリウム等)およびガラスが好ましい。
これらの樹脂材料の中では、アクリレート樹脂、エポキシ樹脂、オレフィン樹脂、ポリベンゾオキサゾール樹脂、シリコーン樹脂およびポリイミド樹脂が好ましい。
なお、この処理による効果をより発揮させるために、表面処理した基材を更に加熱処理してもよい。
<化学式(IV)で示されるトリアゾールシラン化合物を含有する表面処理液>
本発明の表面処理液は、前記のトリアゾールシラン化合物(IV)を含有する表面処理液であるが、このトリアゾールシラン化合物(IV)は、以下の化学式(I)と化学式(IVa)~(IVc)で示されるトリアゾールシラン化合物を包含する。
同様に、化学式(IVa)で示されるトリアゾールシラン化合物(以下、トリアゾールシラン化合物(IVa)ということがある)は、nが1である場合のトリアゾールシラン化合物であり、化学式(IVb)で示されるトリアゾールシラン化合物(以下、トリアゾールシラン化合物(IVb)ということがある)は、nが2である場合のトリアゾールシラン化合物であり、化学式(IVc)で示されるトリアゾールシラン化合物(以下、トリアゾールシラン化合物(IVc)ということがある)は、nが3である場合のトリアゾールシラン化合物である。
このトリアゾールシラン化合物(I)の例としては、前述のとおりである。
なお、可溶化剤と水を使用する場合の表面処理液の調製方法については、当該トリアゾールシラン化合物と水を混合した後に可溶化剤を加えてもよいし、当該トリアゾールシラン化合物と、水および可溶化剤の混合液を混合してもよいし、当該トリアゾールシラン化合物と可溶化剤を混合した後に水を加えてもよい。
また、表面処理液の調製に用いられる水としては、イオン交換水や蒸留水等の純水が好ましい。
本発明のトリアゾールシラン化合物(I)は、前述のとおり、水と接触すると加水分解されるが、この加水分解の態様をスキーム(B)に示す。
このスキーム(B)においては、前記のトリアゾールシラン化合物(I)、(IVa)および(IVb)の有するシリル基が加水分解される態様、即ち、トリアルコキシシリル基が、漸次、ジアルコキシヒドロキシシリル基、ジヒドロキシアルコキシシリル基、トリヒドロキシシリル基に変化する様が示される。
例えば、銅と樹脂材料との接着を例に挙げると、本発明の実施において用いるトリアゾールシラン化合物は、分子中にトリアゾール環とアルコキシシリル基(-Si-OR)を有しており、トリアゾール環は、樹脂および銅と相互作用し、化学結合を形成する。
また、アルコキシシリル基は加水分解を受けて、ヒドロキシシリル基(-Si-OH)に変換され、このヒドロキシシリル基は銅の表面に点在する酸化銅と化学結合する。
従って、銅と表面処理液を接触させることにより、該銅の表面にはトリアゾール環やヒドロキシシリル基との結合により、トリアゾールシラン化合物(IV)に由来する化成皮膜が形成されて、この化成皮膜の表面に樹脂材料からなる樹脂層を形成させた場合には、銅の表面に直に樹脂層を形成させる場合に比べて、銅と樹脂材料との接着性を高めることができる。
この濃度が0.001重量%未満である場合には、接着性の向上効果が十分ではなく、この濃度が10重量%を超える場合には、接着性の向上効果がほぼ頭打ちとなり、トリアゾールシラン化合物の使用量が増えるばかりで経済的ではない。
これを避けるために、表面処理液の調製には、水に難溶性であるシランオリゴマーの可溶化剤として、有機溶剤を表面処理液中に含有させることが好ましい。また、表面処理液の調製においては、トリアゾールシラン化合物の溶解を促進させる為に、酸やアルカリを含有させることが好ましい。なお、前記の有機溶剤は、トリアゾールシラン化合物の溶解性を高める機能も有しているから、本発明の表面処理液には、可溶化剤として、酸、アルカリ、有機溶剤からなる群から選択される少なくとも1種を含有させることが好ましい。
3-メルカプトプロピルトリメトキシシラン、
3-メルカプトプロピルメチルジメトキシシラン等のメルカプトシラン化合物、
ビニルトリクロルシラン、
ビニルトリメトキシシラン、
ビニルトリエトキシシラン等のビニルシラン化合物、
p-スチリルトリメトキシシラン等のスチリルシラン化合物、
2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン、
3-グリシドキシプロピルトリメトキシシラン、
3-グリシドキシプロピルメチルジエトキシシラン、
3-グリシドキシプロピルトリエトキシシラン等のエポキシシラン化合物、
3-アクリロキシプロピルトリメトキシシラン等のアクリロキシシラン化合物、
3-メタクリロキシプロピルメチルジメトキシシラン、
3-メタクリロキシプロピルトリメトキシシラン、
3-メタクリロキシプロピルメチルジエトキシシラン、
3-メタクリロキシプロピルトリエトキシシラン等のメタクリロキシシラン化合物、
N-2-(アミノエチル)-3-アミノプロピルメチルジメトキシシラン、
N-2-(アミノエチル)-3-アミノプロピルトリメトキシシラン、
N-2-(アミノエチル)-3-アミノプロピルトリエトキシシラン、
3-アミノプロピルトリメトキシシラン、
3-アミノプロピルトリエトキシシラン、
3-トリエトキシシリル-N-(1,3-ジメチル-ブチリデン)プロピルアミン、
N-フェニル-3-アミノプロピルトリメトキシシラン、
N-(ビニルベンジル)-2-アミノエチル-3-アミノプロピルトリメトキシシラン等のアミノシラン化合物、
3-ウレイドプロピルトリエトキシシラン等のウレイドシラン化合物、
3-クロロプロピルトリメトキシシラン等のクロロプロピルシラン化合物、
ビス(トリエトキシシリルプロピル)テトラスルフィド等のスルフィドシラン化合物、および
3-イソシアナトプロピルトリエトキシシラン等のイソシアナトシラン化合物
等を挙げることができる。
その他、アルミニウム系カップリング剤、チタン系カップリング剤、ジルコニウム系カップリング剤等も挙げることができる。
本発明の表面処理液を基材の表面に接触させる方法としては、特に制限はなく、前述のシランカップリング剤の場合と同様に、スプレー、浸漬や塗布等の手段を採用することができる。
表面処理液と基材を接触させる時間(処理時間)については、1秒~10分とすることが好ましく、5秒~3分とすることがより好ましい。処理時間が1秒未満の場合には基材表面に形成される化成皮膜の膜厚が薄くなり、材質の異なる材料間の接着力が十分に得られず、一方10分より長くしても、化成皮膜の膜厚に大差はなく、接着性の向上も期待できない。
また、表面処理液を基材表面に接触させる際の処理液の温度については、5~50℃とすることが好ましいが、前記の処理時間との関係において、適宜設定すればよい。
乾燥は、室温~150℃の温度とすることが好ましい。
なお、水洗に用いる水としては、イオン交換水や蒸留水等の純水が好ましいが、水洗の方法や時間には特に制限なく、スプレーや浸漬等の手段による適宜の時間で構わない。
銅イオンを含む水溶液の銅イオン源としては、水に溶解する銅塩であれば特に限定されず、硫酸銅、硝酸銅、塩化銅、ギ酸銅、酢酸銅などの銅塩が挙げられる。銅塩を水に可溶化するために、アンモニアや塩酸などを添加してもよい。
酸性水溶液およびアルカリ性水溶液は、特に限定されないが、酸性水溶液としては、硫酸、硝酸、塩酸等の鉱酸を含む水溶液や、ギ酸、酢酸、乳酸、グリコール酸、アミノ酸などの有機酸を含む水溶液等が挙げられる。アルカリ性水溶液としては、水酸化ナトリウム、水酸化カリウムなどのアルカリ金属の水酸化物や、アンモニア、エタノールアミン、モノプロパノールアミン、テトラメチルアンモニウムヒドロキシド等のアミン類、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム、炭酸水素カリウム、炭酸アンモニウム、炭酸水素アンモニウム、酢酸ナトリウム、酢酸カリウム、リン酸ナトリウム、リン酸水素二ナトリウム、リン酸カリウム、リン酸水素二カリウム等を含む水溶液が挙げられる。
接着方法としては、公知の方法により行うことができる。金属、無機材料または樹脂材料からなる基材の表面に本発明の表面処理液を接触させて化成皮膜を形成し、形成した化成皮膜の一部または全体に他の基材を塗布、圧着、混合等の手段や、接着剤、接着シート(フィルム)の利用あるいはこれらの手段を組み合わせて接着する方法が挙げられる。
また、金属、無機材料、樹脂材料から選択される2つの基材の表面に、本発明の表面処理液を接触させて、2つの基材の表面にそれぞれ化成皮膜を形成し、2つの基材を塗布、圧着、混合等の手段や、接着剤、接着シート(フィルム)の利用あるいはこれらの手段を組み合わせて接着する方法が挙げられる。
また、半導体ウェハ上に再配線層を形成するパッケージ基板(WL-CSP)において、銅回路再配線層と絶縁材料との接着性(密着性)を高めることを目的とする銅回路再配線層の表面処理に好適である。
前記の保護膜や絶縁材料としては、例えば、ポリイミド樹脂やポリベンゾオキサゾール樹脂、シリコーン樹脂などが上げられる。
また、前記の水洗の方法についても特に制限はないが、洗浄水中への銅配線の浸漬または洗浄水による銅配線表面へのスプレーが簡便かつ確実であり好ましい。
前記の絶縁樹脂層の形成には、公知の方法、例えば半硬化の樹脂材料を貼り付ける方法や溶剤を含む液状の樹脂材料を塗布する手段等を採用することができる。次いで、上下の配線を導通させる為に、ビアホールを形成する。このプロセスを繰り返すことにより、多層プリント配線板を作製できる。
(a)絶縁性基板またはスルーホール貫通孔及びビア孔を有する絶縁性基板の第1面及び第1面とは反対側の第2面並びにスルーホール貫通孔及びビア孔内壁に第1導電層を有する絶縁性基板を準備する工程、
(b)第1面および第2面に光架橋性樹脂層及びマスク層を形成して、第1面および第2面並びにスルーホール貫通孔及びビア孔内壁の第1導電層を光架橋性樹脂層及びマスク層で覆う工程、
(c)第1面及び第2面並びにスルーホール貫通孔及びビア孔周辺の光架橋性樹脂層をパターン露光する工程、
(d)第1面及び第2面並びにスルーホール貫通孔及びビア孔周辺のマスク層を除去する工程、
(e)光架橋性樹脂層除去液を使用して、第1面及び第2面、並びにスルーホール貫通孔及びビア孔周辺の未硬化光架橋性樹脂層を現像除去し、第1面上の第1導電層及び第2面上の第1導電層並びにスルーホール貫通孔及びビア孔周辺の第1導電層を露出する工程、
(f)第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁に露出している第1導電層上に電解めっき処理により第2導電層を形成する工程、
(g)第1面上及び第2面上並びにスルーホール貫通孔及びビア孔周辺の硬化光架橋性樹脂層を除去して、第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁の第1及び第2導電層を露出する工程、
(h)露出する第1導電層をフラッシュエッチングして除去する工程、
(i)第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁の第1及び第2導電層に無電解めっき及び電解めっき処理により第3導電層を形成する工程、
(j)第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁の第1、第2及び第3導電層上に絶縁樹脂層を積層する工程、を少なくとも1つ以上含む回路基板の製造方法において、第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁の第1、第2及び第3導電層、絶縁樹脂基板、エッチングレジスト層やめっきレジスト層に使用する光架橋性樹脂層、絶縁樹脂積層の内の少なくとも1つ以上の金属層もしくはレジスト層に本発明の表面処理液を接触させ、プリント配線板を製造する。
(a)絶縁性基板またはスルーホール貫通孔及びビア孔を有する絶縁性基板の第1面及び第1面とは反対側の第2面並びにスルーホール貫通孔及びビア孔内壁に第1導電層を有する絶縁性基板を準備する工程、
(b)第1面および第2面に光架橋性樹脂層及びマスク層を形成して、第1面および第2面並びにスルーホール貫通孔及びビア孔内壁の第1導電層を光架橋性樹脂層及びマスク層で覆う工程、
(c)第1面及び第2面並びにスルーホール貫通孔及びビア孔周辺の光架橋性樹脂層をパターン露光する工程、
(d)第1面及び第2面並びにスルーホール貫通孔及びビア孔周辺のマスク層を除去する工程、
(e)光架橋性樹脂層除去液を使用して、第1面及び第2面、並びにスルーホール貫通孔及びビア孔周辺の未硬化光架橋性樹脂層を現像除去し、第1面上の第1導電層及び第2面上の第1導電層並びにスルーホール貫通孔及びビア孔周辺の第1導電層を露出する工程、
(f)第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁に露出している第1導電層をエッチングして除去する工程、
(g)第1面上及び第2面上並びにスルーホール貫通孔及びビア孔周辺の硬化光架橋性樹脂層を除去して、第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁の第1及び第2導電層を露出する工程、
(h)第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁の第1及び第2導電層に無電解めっき及び電解めっき処理により第3導電層を形成する工程、
(i)第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁の第1、第2及び第3導電層上に絶縁樹脂層を積層する工程、を少なくとも1つ以上含む回路基板の製造方法において、第1面上及び第2面上並びにスルーホール貫通孔及びビア孔内壁の第1、第2及び第3導電層、絶縁樹脂基板、エッチングレジスト層やめっきレジスト層に使用する光架橋性樹脂層、絶縁樹脂積層の内の少なくとも1つ以上の金属層もしくはレジスト層に本発明の表面処理液を接触させ、プリント配線板を製造する。
本発明のシランカップリング剤を、樹脂材料または無機材料に含有させることにより絶縁性組成物とすることができる。
また、トリアゾールシラン化合物(IV)を有機溶剤等に溶解して、樹脂材料または無機材料と混合することにより絶縁性組成物を得ることもできる。
前記絶縁性組成物は公知の方法により作製することができる。例えば、トリアゾールシラン化合物(IV)を有機溶剤に溶解させ、固形または液状の樹脂材料に混合することにより、絶縁性組成物を作製することができる。また、トリアゾールシラン化合物(IV)を液状の樹脂材料に直接添加して混合して、絶縁性組成物を作製してもよい。
また、前記金属表面には、予め表面処理として、浸漬めっき液により錫等の接着性金属層を形成してよいとされている。
本発明の表面処理液は、前記のシランカップリング剤を含む液として用いることができるものである。なお、この特許公報に記載された事項は、引用により本明細書の一部を成すものとする。
なお、合成試験に使用した原料のトリアゾール化合物およびハロゲン化アルキルシラン化合物は、以下のとおりである。
[トリアゾール化合物]
・3,5-ジアミノ-1,2,4-トリアゾール:東京化成工業社製
・3,5-ジメチル-1,2,4-トリアゾール:同上
・3-フェニル-1,2,4-トリアゾール:「J.Org.Chem.,44巻,4160頁(1979年)」に記載された方法に準拠して合成した。
・3-アミノ-5-メチルチオ-1,2,4-トリアゾール:東京化成工業社製
・5-メチル-3-オクチル-1,2,4-トリアゾール:米国特許第5,098,920号明細書に記載された方法に準拠して合成した。
・3-アミノ-1,2,4-トリアゾール:東京化成工業社製
[ハロゲン化アルキルシラン化合物]
・3-クロロプロピルトリメトキシシラン:信越化学工業社製
・3-クロロプロピルトリエトキシシラン:東京化成工業社製
・6-ブロモヘキシルトリエトキシシラン:「Tetrahedron,63巻,5076頁(2007年)」に記載された方法に準拠して合成した。
[トリアゾールシラン化合物]
・1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾール:特許文献2に記載された方法に準拠して合成した。
[接着性試験]
(1)試験片
電解銅箔(厚み:35μm)を試験片として使用した。
(2)試験片の処理
以下の工程a~bに従って行った。
a.酸清浄/1分間(室温)、水洗、乾燥/1分間(100℃)
b.実施例および比較例の表面処理液に浸漬/1分間(室温)、水洗、乾燥/1分間(100℃)
(3)試験片と樹脂の接着
処理した試験片のS面(光沢面)に、ガラス布エポキシ樹脂含浸プリプレグ(FR-4グレード)を積層プレスし、試験片と樹脂を接着した。
(4)接着性の評価
「JIS C6481(1996)」に従って、幅10mmの試験片を作成し、プレッシャークッカー処理(121℃/湿度100%/100時間)した後、銅箔の引き剥がし強さ(kN/m)を測定した。
<3,5-ジアミノ-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾールの合成>
3,5-ジアミノ-1,2,4-トリアゾール15.0g(0.151mol)および脱水N,N-ジメチルホルムアミド100mLからなる懸濁液へ、室温にて28%ナトリウムメトキシドメタノール溶液29.2g(0.151mol)を加えて均一溶液として30分間攪拌した後、3-クロロプロピルトリメトキシシラン30.1g(0.151mol)を加え、77~80℃にて4時間攪拌した。
懸濁状の反応液を3℃まで冷却した後、不溶物を濾去し、濾液の溶媒を減圧留去して、褐色粘稠物35.7g(0.137mol、収率90.5%)を得た。
1H-NMR (DMSO-d6) δ:0.51(t, 2H), 1.62(m, 2H), 3.46(s, 9H), 3.58(t, 2H), 4.69(s, 2H), 5.11(s, 2H).
この1H-NMRスペクトルデータより、得られた粘稠物は、化学式(V)で示される標題のトリアゾールシラン化合物であるものと同定した。
<3,5-ジアミノ-1-[3-(トリエトキシシリル)プロピル]-1,2,4-トリアゾールの合成>
3,5-ジアミノ-1,2,4-トリアゾール15.6g(0.157mol)および脱水N,N-ジメチルホルムアミド100mLからなる懸濁液へ、室温にて20%ナトリウムエトキシドエタノール溶液53.5g(0.157mol)を加え、55~60℃に加温して20分間攪拌した後、3-クロロプロピルトリエトキシシラン37.9g(0.157mol)を加え、87~90℃にて6時間攪拌した。
懸濁状の反応液を3℃まで冷却した後、不溶物を濾去し、濾液の溶媒を減圧留去して、褐色粘稠物42.3g(0.139mol、収率88.8%)を得た。
1H-NMR (DMSO-d6) δ:0.49(t, 2H), 1.14(t, 9H), 1.62(m, 2H), 3.56(t, 2H), 3.73(q, 6H), 4.67(s, 2H), 5.11(s, 2H).
この1H-NMRスペクトルデータより、得られた粘稠物は、化学式(VI)で示される標題のトリアゾールシラン化合物であるものと同定した。
<3,5-ジメチル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾールの合成>
3,5-ジメチル-1,2,4-トリアゾール10.5g(0.108mol)および脱水N,N-ジメチルホルムアミド60mLからなる溶液へ、室温にて28%ナトリウムメトキシドメタノール溶液20.7g(0.107mol)を加え、20分間攪拌した後、3-クロロプロピルトリメトキシシラン21.6g(0.109mol)を加え、90~93℃にて4時間攪拌した。
懸濁状の反応液を2℃まで冷却した後、不溶物を濾去し、続いて、濾液の溶媒を減圧留去し、生じた少量の不溶物を濾去して、微褐色液体24.6g(0.095mol、収率87.8%)を得た。
1H-NMR (DMSO-d6) δ:0.54(t, 2H), 1.76(m, 2H), 2.15(s, 3H), 2.31(s, 3H), 3.47(s, 9H), 3.94(t, 2H).
この1H-NMRスペクトルデータより、得られた液体は、化学式(VII)で示される標題のトリアゾールシラン化合物であるものと同定した。
<3-フェニル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾールの合成>
3-フェニル-1,2,4-トリアゾール17.4g(0.120mol)および脱水N,N-ジメチルホルムアミド90mLからなる溶液へ、室温にて28%ナトリウムメトキシドメタノール溶液23.3g(0.121mol)を加え、20分間攪拌した後、3-クロロプロピルトリメトキシシラン23.8g(0.120mol)を加え、88~90℃にて4時間攪拌した。
懸濁状の反応液を2℃まで冷却した後、不溶物を濾去し、続いて、濾液の溶媒を減圧留去し、生じた少量の不溶物を濾去して、微桃色液体34.2g(0.111mol、収率92.7%)を得た。
1H-NMR (DMSO-d6) δ:0.58(t, 2H), 1.90(m, 2H), 3.48(s, 9H), 4.20(t, 2H), 7.41-7.48(m, 2H), 8.01-8.05(m, 3H), 8.67(s, 1H).
この1H-NMRスペクトルデータより、得られた液体は、化学式(VIII)で示される標題のトリアゾールシラン化合物であるものと同定した。
<5-アミノ-3-メチルチオ-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾールの合成>
3-アミノ-5-メチルチオ-1,2,4-トリアゾール10.0g(0.0768mol)および脱水N,N-ジメチルホルムアミド60mLからなる溶液へ、室温にて28%ナトリウムメトキシドメタノール溶液14.8g(0.0767mol)を加え、20分間攪拌した後、3-クロロプロピルトリメトキシシラン15.4g(0.0775mol)を加え、88~90℃にて4時間攪拌した。
懸濁状の反応液を2℃まで冷却した後、不溶物を濾去し、続いて、濾液の溶媒を減圧留去し、少量の不溶物を濾去して、赤褐色液体21.5g(0.0735mol、収率95.7%)を得た。
1H-NMR (DMSO-d6) δ:0.54(t, 2H), 1.70(m, 2H), 2.38(s, 3H), 3.47(s, 9H), 3.75(t, 2H).
この1H-NMRスペクトルデータより、得られた液体は、化学式(IX)で示される標題のトリアゾールシラン化合物であるものと同定した。
<5-メチル-3-オクチル-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾールの合成>
5-メチル-3-オクチル-1,2,4-トリアゾール9.0g(0.0461mol)および脱水N,N-ジメチルホルムアミド50mLからなる溶液へ、室温にて28%ナトリウムメトキシドメタノール溶液9.00g(0.0466mol)を加え、20分間攪拌した後、3-クロロプロピルトリメトキシシラン9.26g(0.0466mol)を加え、90~92℃にて4時間攪拌した。
懸濁状の反応液を2℃まで冷却した後、不溶物を濾去し、続いて、濾液の溶媒を減圧留去し、少量の不溶物を濾去して、淡褐色液体14.3g(0.0400mol、収率86.8%)を得た。
1H-NMR (DMSO-d6) δ:0.52(m, 2H), 0.85(br s, 3H), 1.1-1.3(br s, 10H), 1.58(br s, 2H), 1.75(m, 2H), 2.16(s, 3H), 2.62(t, 2H), 3.46(s, 9H), 3.94(t, 2H).
この1H-NMRスペクトルデータより、得られた液体は、化学式(X)で示される標題のトリアゾールシラン化合物であるものと同定した。
<3-アミノ-1-[6-(トリエトキシシリル)ヘキシル]-1,2,4-トリアゾールの合成>
3-アミノ-1,2,4-トリアゾール5.50g(0.0654mol)および脱水N,N-ジメチルホルムアミド50mLからなる溶液へ、室温にて20%ナトリウムエトキシドエタノール溶液22.3g(0.0655mol)を加え、51~52℃に加温して20分間攪拌した後、6-ブロモヘキシルトリエトキシシラン21.3g(0.0651mol)を5分間かけて滴下し、78~80℃にて3時間攪拌した。
懸濁状の反応液を2℃まで冷却した後、不溶物を濾去し、濾液を減圧下に28gまで濃縮した。これにジエチルエーテル50mLを加えた後、不溶物を濾去し、続いて、濾液の溶媒を減圧留去して、淡褐色液体19.8g(0.0600mol、収率91.6%)を得た。
1H-NMR (CDCl3) δ:0.61(t, 2H), 1.22(t, 9H), 1.2-1.4(m, 6H), 1.62(m, 2H), 3.42(t, 2H), 3.48(q, 6H), 7.64(s, 1H).
この1H-NMRスペクトルデータより、得られた液体は、化学式(XI)で示される標題のトリアゾールシラン化合物であるものと同定した。
<3-アミノ-1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾールの合成>
3-アミノ-1,2,4-トリアゾール20.4g(0.243mol)および脱水N,N-ジメチルホルムアミド100mLからなる溶液へ、室温にて28%ナトリウムメトキシドメタノール溶液46.7g(0.242mol)を加えて30分間攪拌した後、3-クロロプロピルトリメトキシシラン48.3g(0.243mol)を加え、86~90℃にて8時間攪拌した。
懸濁状の反応液を3℃まで冷却した後、不溶物を濾去し、濾液の溶媒を減圧留去して、黄褐色液体57.6g(0.234mol、収率96.4%)を得た。
1H-NMR (DMSO-d6) δ:0.51(t, 2H), 1.73(m, 2H), 3.46(s, 9H), 3.86(t, 2H), 5.21(s, 2H), 7.91(s, 1H).
この1H-NMRスペクトルデータより、得られた液体は、化学式(XII)で示される標題のトリアゾールシラン化合物であるものと同定した。
[実施例9]
シランカップリング剤成分として、実施例1において合成したトリアゾールシラン化合物を使用して銅の表面処理液を調製した。
即ち、当該トリアゾールシラン化合物10gにエチレングリコールモノブチルエーテル200gを加え、続いて水790gを加えて、室温にて2時間攪拌し、銅の表面処理液(以下、処理液Aと云う)を調製した。
この処理液Aについて、当該トリアゾールシラン化合物のトリメトキシシリル基が、トリヒドロキシシリル基に加水分解されていることを確認し、接着性試験を行った。
得られた試験結果は、表1に示したとおりであった。
実施例9と同様にして、実施例1において合成したトリアゾールシラン化合物の代わりに、実施例2~8において合成したトリアゾールシラン化合物を使用して、銅の表面処理液(以下、各々処理液B、C、D、E、F、G、Hと云う)を調製した。
これらの処理液中のトリアゾールシラン化合物のトリメトキシシリル基またはトリエトキシシリル基が、トリヒドロキシシリル基に加水分解されていることを確認し、接着性試験を行った。
得られた試験結果は、表1に示したとおりであった。
実施例9と同様にして、実施例1において合成したトリアゾールシラン化合物の代わりに、1-[3-(トリメトキシシリル)プロピル]-1,2,4-トリアゾールを使用して、銅の表面処理液(以下、処理液Iと云う)を調製した。
この処理液Iについて、当該トリアゾールシラン化合物のトリメトキシシリル基が、トリヒドロキシシリル基に加水分解されていることを確認し、接着性試験を行った。
得られた試験結果は、表1に示したとおりであった。
シランカップリング剤成分を使用しない以外は、前記の処理液Aと同様の組成を有する銅の表面処理液(以下、処理液Jと云う)を調製し、接着性試験を行った。
得られた試験結果は、表1に示したとおりであった。
特に、アミノ基またはフェニル基を有するトリアゾールシラン化合物の場合に、銅と樹脂の接着力を高める効果が顕著であり、中でも、2つのアミノ基を有するトリアゾールシラン化合物の場合には、前記の接着力が飛躍的に高められている。
また、本発明によれば、金属、無機材料および樹脂材料の接着性(密着性)を十分に確保できるので、基材の表面を粗化することなく、平滑な状態に保持することができる。従って、本発明は、多層プリント配線板の小型化、薄型化、高周波化、高密度化等の実現に大いに貢献し得るものであるから、産業上の利用可能性は多大である。
Claims (34)
- 金属、無機材料および樹脂材料からなる群から選択される少なくとも1つの表面を処理するために用いる請求項4に記載の表面処理液。
- 金属、無機材料および樹脂材料からなる群から選択される2つの材料を接着するために用いる請求項4に記載の表面処理液。
- 前記金属が、銅、アルミニウム、チタン、ニッケル、錫、鉄、銀、金およびこれらの合金からなる群から選択される少なくとも1つである請求項5または請求項6に記載の表面処理液。
- 前記金属が銅または銅合金である請求項5または請求項6に記載の表面処理液。
- 前記無機材料が、シリコン、セラミックおよびガラスからなる群から選択される少なくとも1つである請求項5または請求項6に記載の表面処理液。
- 前記セラミックが、アルミナ、炭化ケイ素、窒化アルミ、窒化ケイ素およびチタン酸バリウムからなる群から選択される少なくとも1つである請求項9に記載の表面処理液。
- 前記樹脂材料が、アクリレート樹脂、エポキシ樹脂、オレフィン樹脂、ポリベンゾオキサゾール樹脂、シリコーン樹脂およびポリイミド樹脂からなる群から選択される少なくとも1つである請求項5または請求項6に記載の表面処理液。
- 請求項4に記載の表面処理液を金属の表面に接触させる金属の表面処理方法。
- 前記金属が、銅、アルミニウム、チタン、ニッケル、錫、鉄、銀、金およびこれらの合金からなる群から選択される少なくとも1つである請求項12に記載の金属の表面処理方法。
- 前記金属が、銅または銅合金である請求項12に記載の金属の表面処理方法。
- 前記表面処理液を銅または銅合金の表面に接触させる前に、銅イオンを含む水溶液を前記銅または銅合金の表面に接触させる請求項14に記載の金属の表面処理方法。
- 前記表面処理液を銅または銅合金の表面に接触させた後に、酸性水溶液またはアルカリ性水溶液を前記銅または銅合金の表面に接触させる請求項14または請求項15に記載の金属の表面処理方法。
- 請求項4に記載の表面処理液を無機材料の表面に接触させる無機材料の表面処理方法。
- 前記無機材料が、シリコン、セラミックおよびガラスからなる群から選択される少なくとも1つである請求項17に記載の無機材料の表面処理方法。
- 前記セラミックが、アルミナ、炭化ケイ素、窒化アルミ、窒化ケイ素およびチタン酸バリウムからなる群から選択される少なくとも1つである請求項18に記載の無機材料の表面処理方法。
- 請求項4に記載の表面処理液を樹脂材料の表面に接触させる樹脂材料の表面処理方法。
- 前記樹脂材料が、アクリレート樹脂、エポキシ樹脂、オレフィン樹脂、ポリベンゾオキサゾール樹脂、シリコーン樹脂およびポリイミド樹脂からなる群から選択される少なくとも1つである請求項20に記載の樹脂材料の表面処理方法。
- 金属と樹脂材料の接着方法であって、
請求項4に記載の表面処理液を、金属および樹脂材料の少なくとも一方に接触させて当該少なくとも一方に化成皮膜を形成し、前記金属と前記樹脂材料とを前記化成皮膜を介して互いに接着する金属と樹脂材料の接着方法。 - 無機材料と樹脂材料の接着方法であって、
請求項4に記載の表面処理液を、無機材料および樹脂材料の少なくとも一方に接触させて当該少なくとも一方に化成皮膜を形成し、前記無機材料と前記樹脂材料とを前記化成皮膜を介して互いに接着する無機材料と樹脂材料の接着方法。 - 金属と無機材料の接着方法であって、
請求項4に記載の表面処理液を、金属および無機材料の少なくとも一方に接触させて当該少なくとも一方に化成皮膜を形成し、前記金属と前記無機材料とを前記化成皮膜を介して互いに接着する金属と無機材料の接着方法。 - 金属、無機材料および樹脂材料からなる群から選択される2つの材料を、請求項4に記載の表面処理液により形成された化成皮膜を介して接着したプリント配線板。
- 金属、無機材料および樹脂材料からなる群から選択される2つの材料を、請求項4に記載の表面処理液により形成された化成皮膜を介して接着した半導体ウェハ。
- 金属、無機材料および樹脂材料からなる群から選択される2つの材料を、請求項4に記載の表面処理液により形成された化成皮膜を介して接着した電子デバイス。
- 請求項3に記載のシランカップリング剤と樹脂材料または無機材料とを含有する絶縁性組成物。
- 前記樹脂材料が、アクリレート樹脂、エポキシ樹脂、オレフィン樹脂、ポリベンゾオキサゾール樹脂、シリコーン樹脂およびポリイミド樹脂からなる群から選択される少なくとも1つである請求項28に記載の絶縁性組成物。
- 前記無機材料が、シリコン、セラミックおよびガラスからなる群から選択される少なくとも1つである請求項28に記載の絶縁性組成物。
- 請求項28~請求項30のいずれか一項に記載の絶縁性組成物を含有する絶縁材料。
- 請求項28~請求項30のいずれか一項に記載の絶縁性組成物から得られる絶縁層を有するプリント配線板。
- 請求項28~請求項30のいずれか一項に記載の絶縁性組成物から得られる絶縁層を有する半導体ウェハ。
- 請求項28~請求項30のいずれか一項に記載の絶縁性組成物から得られる絶縁層を有する電子デバイス。
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KR20220057532A (ko) | 2019-09-06 | 2022-05-09 | 시코쿠가세이고교가부시키가이샤 | 금속의 표면 처리액 및 그의 농축액, 금속의 표면 처리액 세트 및 표면 처리 방법, 및 프린트 배선판의 제조 방법 |
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US12091430B2 (en) | 2019-09-06 | 2024-09-17 | Shikoku Chemicals Corporation | Metal surface treatment liquid and liquid concentrate thereof, metal surface treatment liquid set, metal surface treatment method, and method for manufacturing printed wiring board |
US11230644B1 (en) | 2020-07-20 | 2022-01-25 | Mec Company Ltd. | Coating film-forming composition, method for producing surface-treated metal member, and method for producing metal-resin composite |
WO2023127679A1 (ja) | 2021-12-28 | 2023-07-06 | 四国化成工業株式会社 | 金属の表面処理液 |
WO2023127681A1 (ja) | 2021-12-28 | 2023-07-06 | 四国化成工業株式会社 | 有機被膜およびその製造方法 |
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TW201841929A (zh) | 2018-12-01 |
US20200031852A1 (en) | 2020-01-30 |
JPWO2018186476A1 (ja) | 2020-02-20 |
EP3608327B1 (en) | 2022-05-04 |
CN110475782A (zh) | 2019-11-19 |
KR102405049B1 (ko) | 2022-06-02 |
KR20190135484A (ko) | 2019-12-06 |
CN110475782B (zh) | 2022-05-17 |
JP6905585B2 (ja) | 2021-07-21 |
US11680076B2 (en) | 2023-06-20 |
EP3608327A4 (en) | 2020-12-16 |
TWI732114B (zh) | 2021-07-01 |
EP3608327A1 (en) | 2020-02-12 |
SG11201909186YA (en) | 2019-11-28 |
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