TWI431157B - 苯基萘基咪唑化合物及其用途 - Google Patents
苯基萘基咪唑化合物及其用途 Download PDFInfo
- Publication number
- TWI431157B TWI431157B TW094119281A TW94119281A TWI431157B TW I431157 B TWI431157 B TW I431157B TW 094119281 A TW094119281 A TW 094119281A TW 94119281 A TW94119281 A TW 94119281A TW I431157 B TWI431157 B TW I431157B
- Authority
- TW
- Taiwan
- Prior art keywords
- naphthyl
- phenyl
- copper
- surface treatment
- treatment agent
- Prior art date
Links
- -1 Phenylnaphthylimidazole compound Chemical class 0.000 title claims description 63
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 48
- 229910052802 copper Inorganic materials 0.000 claims description 47
- 239000010949 copper Substances 0.000 claims description 47
- 239000012756 surface treatment agent Substances 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 25
- 229910000881 Cu alloy Inorganic materials 0.000 claims description 20
- 235000002639 sodium chloride Nutrition 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- PVNCLKDZXOOJMO-UHFFFAOYSA-N 5-methyl-4-naphthalen-2-yl-2-phenyl-1h-imidazole Chemical compound N=1C(C=2C=C3C=CC=CC3=CC=2)=C(C)NC=1C1=CC=CC=C1 PVNCLKDZXOOJMO-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- JQJKWVIUFZWDPH-UHFFFAOYSA-N 5-naphthalen-1-yl-2-phenyl-1h-imidazole Chemical compound N=1C(C=2C3=CC=CC=C3C=CC=2)=CNC=1C1=CC=CC=C1 JQJKWVIUFZWDPH-UHFFFAOYSA-N 0.000 claims description 9
- LFNLCLNDJHARGR-UHFFFAOYSA-N 5-naphthalen-2-yl-2-phenyl-1h-imidazole Chemical compound N=1C(C=2C=C3C=CC=CC3=CC=2)=CNC=1C1=CC=CC=C1 LFNLCLNDJHARGR-UHFFFAOYSA-N 0.000 claims description 9
- 150000002366 halogen compounds Chemical class 0.000 claims description 9
- 238000003466 welding Methods 0.000 claims description 9
- INQRDWQKHMKYTQ-UHFFFAOYSA-N 5-methyl-4-naphthalen-1-yl-2-phenyl-1h-imidazole Chemical compound N=1C(C=2C3=CC=CC=C3C=CC=2)=C(C)NC=1C1=CC=CC=C1 INQRDWQKHMKYTQ-UHFFFAOYSA-N 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 238000004381 surface treatment Methods 0.000 claims description 7
- BQMLFRCDMWYVTQ-UHFFFAOYSA-N 2-naphthalen-1-yl-5-phenyl-1h-imidazole Chemical compound C=1NC(C=2C3=CC=CC=C3C=CC=2)=NC=1C1=CC=CC=C1 BQMLFRCDMWYVTQ-UHFFFAOYSA-N 0.000 claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 6
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 6
- XVGQHMYCDALKKN-UHFFFAOYSA-N 2-naphthalen-2-yl-5-phenyl-1h-imidazole Chemical compound C=1NC(C=2C=C3C=CC=CC3=CC=2)=NC=1C1=CC=CC=C1 XVGQHMYCDALKKN-UHFFFAOYSA-N 0.000 claims description 5
- IKJYRWQCYXTMFR-UHFFFAOYSA-N 5-methyl-2-naphthalen-1-yl-4-phenyl-1h-imidazole Chemical compound CC=1NC(C=2C3=CC=CC=C3C=CC=2)=NC=1C1=CC=CC=C1 IKJYRWQCYXTMFR-UHFFFAOYSA-N 0.000 claims description 4
- GBEHYVGDLPXPIS-UHFFFAOYSA-N 5-methyl-2-naphthalen-2-yl-4-phenyl-1h-imidazole Chemical compound CC=1NC(C=2C=C3C=CC=CC3=CC=2)=NC=1C1=CC=CC=C1 GBEHYVGDLPXPIS-UHFFFAOYSA-N 0.000 claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001880 copper compounds Chemical class 0.000 claims description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 4
- 150000003752 zinc compounds Chemical class 0.000 claims description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 235000010755 mineral Nutrition 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000001103 potassium chloride Substances 0.000 claims description 3
- 235000011164 potassium chloride Nutrition 0.000 claims description 3
- DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims description 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 2
- 239000005750 Copper hydroxide Substances 0.000 claims description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
- CANRESZKMUPMAE-UHFFFAOYSA-L Zinc lactate Chemical compound [Zn+2].CC(O)C([O-])=O.CC(O)C([O-])=O CANRESZKMUPMAE-UHFFFAOYSA-L 0.000 claims description 2
- RAOSIAYCXKBGFE-UHFFFAOYSA-K [Cu+3].[O-]P([O-])([O-])=O Chemical compound [Cu+3].[O-]P([O-])([O-])=O RAOSIAYCXKBGFE-UHFFFAOYSA-K 0.000 claims description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims description 2
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 2
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 2
- 229940045803 cuprous chloride Drugs 0.000 claims description 2
- 239000011698 potassium fluoride Substances 0.000 claims description 2
- 235000003270 potassium fluoride Nutrition 0.000 claims description 2
- 239000011775 sodium fluoride Substances 0.000 claims description 2
- 235000013024 sodium fluoride Nutrition 0.000 claims description 2
- 235000009518 sodium iodide Nutrition 0.000 claims description 2
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- 239000011746 zinc citrate Substances 0.000 claims description 2
- 235000006076 zinc citrate Nutrition 0.000 claims description 2
- 229940068475 zinc citrate Drugs 0.000 claims description 2
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 claims description 2
- 239000011576 zinc lactate Substances 0.000 claims description 2
- 235000000193 zinc lactate Nutrition 0.000 claims description 2
- 229940050168 zinc lactate Drugs 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 claims description 2
- 229910000165 zinc phosphate Inorganic materials 0.000 claims description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 2
- 229960001763 zinc sulfate Drugs 0.000 claims description 2
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 claims description 2
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 claims 1
- 229940107816 ammonium iodide Drugs 0.000 claims 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 claims 1
- 229910000679 solder Inorganic materials 0.000 description 70
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 238000012360 testing method Methods 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 238000005476 soldering Methods 0.000 description 20
- 239000010410 layer Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 230000003595 spectral effect Effects 0.000 description 16
- 238000004809 thin layer chromatography Methods 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 230000005496 eutectics Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical compound CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- LQBJWKCYZGMFEV-UHFFFAOYSA-N lead tin Chemical compound [Sn].[Pb] LQBJWKCYZGMFEV-UHFFFAOYSA-N 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- FGMOPLPOIRMOJW-UHFFFAOYSA-N 1-naphthalen-1-ylpropan-2-one Chemical compound C1=CC=C2C(CC(=O)C)=CC=CC2=C1 FGMOPLPOIRMOJW-UHFFFAOYSA-N 0.000 description 5
- OKQHKXIGCVUSRM-UHFFFAOYSA-N 1-naphthalen-2-ylpropan-2-one Chemical compound C1=CC=CC2=CC(CC(=O)C)=CC=C21 OKQHKXIGCVUSRM-UHFFFAOYSA-N 0.000 description 5
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- AZKDTTQQTKDXLH-UHFFFAOYSA-N naphthalene-2-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CC=C21 AZKDTTQQTKDXLH-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RBMWDBHKRZTOMB-UHFFFAOYSA-N 2-ethoxy-1-phenylethanone Chemical compound CCOCC(=O)C1=CC=CC=C1 RBMWDBHKRZTOMB-UHFFFAOYSA-N 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000013058 crude material Substances 0.000 description 3
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WEZYFYMYMKUAHY-UHFFFAOYSA-N tert-butyl 2,4-dibenzylpiperazine-1-carboxylate Chemical compound C1C(CC=2C=CC=CC=2)N(C(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 WEZYFYMYMKUAHY-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Description
本發明係關於一種由以下化學式(I)表示之新穎的苯基萘基咪唑化合物;一種在焊接電子零件或其類似物之過程中對印刷布線板之銅或銅合金所使用之表面處理劑;一種銅或銅合金之表面處理方法;一種印刷布線板;及一種焊接方法。
在此化學式中,當A1
為苯基時,則A2
代表1-萘基或2-萘基,及當A1
為1-萘基或2-萘基時,則A2
代表苯基;及R代表氫原子或甲基。
近年來廣泛地採用具高密度的表面安裝技術。此種表面安裝技術尤其被分類為利用焊料糊結合晶片型零件的雙面表面安裝技術、及混成安裝技術(其係使用焊料糊之晶片型零件之表面安裝技術與個別零件之通孔(through-hole)安裝技術的組合)。在任一安裝方法中,印刷布線板經歷兩個或兩個以上的焊接步驟,因此其會暴露至產生嚴苛熱史的高溫。
經由加熱構成印刷布線板之電路部分之銅或銅合金的表面會加速氧化物膜的形成,因此電路部分之表面無法維持良好的焊接性。
為保護印刷布線板之銅電路部分防止空氣氧化,一般使用表面處理劑將一化學層形成於電路部分之表面上。然而,即使係於銅電路部分經歷多個循環之熱史後,亦需經由防止化學層退化(即,被降解)以保護銅電路部分而維持良好的焊接性。
習慣上使用錫鉛合金共熔焊料於將電子零件安裝至印刷布線板等等之上。然而,近年來擔心焊料合金中所含之鉛會對人體產生不利影響,因此希望使用無鉛焊料。
因此,考慮各種無鉛焊料。舉例來說,已有將一或多種金屬(諸如銀、鋅、鉍、銦、銻、銅等等)添加至錫之基底金屬的無鉛焊料經提出。
習用之錫鉛共熔焊料於基板(尤其係銅)之表面上的可濕性優異,因此其會強烈地黏著至銅,而產生高可靠度。相對地,無鉛焊料於銅表面上之可濕性較習用之錫鉛焊料差,因此其由於空隙及其他黏合瑕疵而呈現不良的焊接性及低黏合強度。
因此,當使用無鉛焊料時,需選擇具優良焊接性的焊料合金及適用於無鉛焊料之助焊劑。用於防止銅或銅合金表面上之氧化的表面處理劑亦需具有改良無鉛焊料之可濕性及焊接性的功能。
許多無鉛焊料具高熔點,及較習用之錫鉛共熔焊料高約20至約50℃之焊接溫度。因此,利用無鉛焊料焊接之方法所用之表面處理劑應具有可形成具優異耐熱性之化學層的特性。
關於此等表面處理劑之活性成分,已有各種咪唑化合物提出。分別舉例來說,專利文件1揭示2-烷基咪唑化合物諸如2-十一基咪唑;專利文件2揭示2-芳基咪唑化合物諸如2-苯基咪唑及2-苯基-4-甲基咪唑;專利文件3揭示2-烷基苯并咪唑化合物諸如2-壬基苯并咪唑;及專利文件4揭示2-芳烷基苯并咪唑化合物諸如2-(4-氯苯甲基)苯并咪唑。
然而,在使用含有此一咪唑化合物之表面處理劑的情況中,形成於銅表面上之化學層的耐熱性尚無法令人滿意。此外,在焊接時,焊料可濕性不足,以致無法得到良好的焊接性。尤其在使用無鉛焊料替代共熔焊料進行焊接的情況中,很難實際使用前述的表面處理劑。
[專利文件1]JP-B-46-17046[專利文件2]JP-A-4-206681[專利文件3]JP-A-5-25407[專利文件4]JP-A-5-186888
本發明係鑑於前述情勢而進行。本發明之一目的為提供一種新穎的苯基萘基咪唑化合物;及提供一種表面處理劑,其在使用共熔焊料或無鉛焊料將電子零件或其類似物安裝至印刷布線板時,於構成印刷布線板或其類似物之電路部分之銅或銅合金之表面上形成具優異耐熱性之化學層,且同時改良對焊料之可濕性,及使焊接性良好;及一種表面處理方法。
此外,本發明之另一目的為提供一種經由使構成銅電路部分之銅或銅合金之表面與前述表面處理劑接觸而產生的印刷布線板;及提供一種經由先使銅或銅合金之表面與前述表面處理劑接觸,然後再使用共熔焊料或無鉛焊料進行焊接的焊接方法。
為解決前述問題,本發明人進行廣泛且密集的研究。結果,發現經由使含有以前述化學式(I)所表示之新穎苯基萘基咪唑化合物作為活性成分之表面處理劑與銅或銅合金之表面接觸,可達成本發明之目的,以致完成本發明。
根據本發明之含有新穎苯基萘基咪唑化合物之表面處理劑不僅可於構成印刷布線板或其類似物之電路部分之銅或銅合金之表面上形成具優異耐熱性之化學層,其並且可大大改良共熔焊料及無鉛焊料對相關表面之可濕性,及使焊接性良好。
此外,由於根據本發明之焊接方法可使用不含有害金屬鉛之焊料,因而其由環保觀點來看有利。
以下將說明實施本發明之最佳方式。
根據本發明之苯基萘基咪唑化合物包括:2-苯基-4-(1-萘基)咪唑,2-苯基-4-(2-萘基)咪唑,2-苯基-4-(1-萘基)-5-甲基咪唑,2-苯基-4-(2-萘基)-5-甲基咪唑,2-(1-萘基)-4-苯基咪唑,2-(2-萘基)-4-苯基咪唑,2-(1-萘基)-4-苯基-5-甲基咪唑,及2-(2-萘基)-4-苯基-5-甲基咪唑。
根據本發明之苯基萘基咪唑化合物可根據已知之方法合成得。換言之,在根據本發明之苯基萘基咪唑化合物中,經分類為2-苯基-4-萘基咪唑化合物(其中咪唑環的2-位次及4-位次分別被苯基及萘基取代)之化合物,即2-苯基-4-(1-萘基)咪唑、2-苯基-4-(2-萘基)咪唑、2-苯基-4-(1-萘基)-5-甲基咪唑、及2-苯基-4-(2-萘基)-5-甲基咪唑,可例如經由使2-鹵化萘基烷基酮化合物與苄脒化合物如以下之反應流程所示,於有機溶劑中在去鹵氫劑之存在下加熱反應而合成得。
在此化學式中,X可代表氯原子、溴原子、或碘原子;及R可代表氫原子或甲基。
在如前述反應流程所示之反應中,以2-鹵化萘基烷基酮化合物計,苄脒化合物之使用量可在自0.8至1.5莫耳倍數的比例中較佳,及自0.9至1.1莫耳倍數更佳。以2-鹵化萘基烷基酮化合物計,去鹵氫劑之使用量係在自1至10當量倍數的比例中較佳。
前述2-鹵化萘基烷基酮化合物的實例包括ω-溴-1-萘乙酮、ω-溴-2-萘乙酮、2-溴-1’-萘丙酮、2-溴-2’-萘丙酮、ω-氯-1-萘乙酮、ω-碘-1-萘乙酮、2-氯-1’-萘丙酮、及2-碘-2’-萘丙酮。
在此等2-鹵化萘基烷基酮化合物中,可取得ω-溴-2-萘乙酮作為試劑。此外,關於除ω-溴-2-萘乙酮外之其他化合物,可使用例如經由將萘基烷基酮化合物之2-位次鹵化而合成得之化合物。關於在2-位次的鹵化,雖然在2-位次的氯化及在2-位次的碘化可行,但經由使1莫耳之萘基烷基酮化合物與1莫耳溴反應而達成之在2-位次的溴化為最簡單。
在萘基烷基酮化合物中,萘乙酮化合物之實例包括1-萘乙酮及2-萘乙酮,此兩者皆係已知且可容易地取得。
在萘基烷基酮化合物中,萘丙酮化合物之實例包括1-萘丙酮及2-萘丙酮。1-萘丙酮可例如經由使用1,2-二氯乙烷或其類似物作為溶劑使萘與丙醯氯.氯化鋁錯合物反應而製得(見稍後說明的參考實施例1)。
2-萘丙酮可例如經由使2-萘甲腈與乙基溴化鎂或其類似物反應,及於強酸性條件下水解反應混合物而製得(見稍後說明的參考實施例2)。
苄脒化合物之實例包括苄脒;苄脒之有機酸鹽諸如苄脒乙酸鹽;及苄脒之無機酸鹽諸如苄脒鹽酸鹽。
關於去鹵氫劑,可使用已知之化合物而無限制。此一去鹵氫劑之實例包括無機鹼諸如氫氧化鈉、氫氧化鉀、氫氧化鈣、碳酸鈉、碳酸鉀、碳酸氫鈉、及碳酸氫鉀;有機鹼諸如三乙胺及1,8-二吖雙環[5.4.0]-7-十一烯(DBU);及金屬烷氧化物化合物諸如甲醇鈉及第三丁氧化鉀。
關於反應溶劑,可使用已知之化合物而無限制,只要其可將例如2-鹵化萘基烷基酮化合物及苄脒化合物溶解於其中,且不會參與反應即可。適當溶劑之實例包括醇諸如乙醇及異丙醇;烴諸如己烷及甲苯;鹵化烴諸如氯仿及氯苯;酯諸如乙酸乙酯;腈諸如乙腈;醚諸如四氫呋喃及二氧陸圜;醯胺諸如二甲基甲醯胺(DMF)及二甲基乙醯胺(DMAC);且除此之外,二甲亞碸(DMSO)。
反應溫度係自室溫至回流溫度較佳;且反應時間係自1至10小時較佳。反應通常可於大氣壓力下進行。
在前述反應條件下生成之2-苯基-4-萘基咪唑化合物可藉由例如以下的分離操作取出。換言之,於反應完成後,可藉由例如將大量水添加至製得之反應混合物或已自反應混合物將溶劑餾除之濃縮物,而製得粗製期望材料之固體。此粗製材料可藉由再結晶操作或其類似操作而純化。
在根據本發明之苯基萘基咪唑化合物中,經分類為2-萘基-4-苯基咪唑化合物(其中咪唑環的2-位次及4-位次分別被萘基及苯基取代,而5-位次則未被取代)之化合物,即2-(1-萘基)-4-苯基咪唑及2-(2-萘基)-4-苯基咪唑,可例如經由使萘甲醛化合物、2-乙醯氧苯乙酮、氨、及醋酸銅(II)如以下之反應流程所示,於水溶性有機溶劑諸如醇中加熱反應而合成得。
在如前述反應流程所示之反應中,以萘甲醛化合物計,2-乙醯氧苯乙酮之使用量可在自0.8至1.5莫耳倍數的比例中較佳,及自0.9至1.1莫耳倍數更佳。以萘甲醛化合物計,氨之使用量可在自10至50莫耳倍數的比例中較佳,及自20至30莫耳倍數更佳。以萘甲醛化合物計,醋酸銅(II)之使用量可在自1至5莫耳倍數的比例中較佳,及自2至3莫耳倍數更佳。
2-乙醯氧苯乙酮可藉由例如使2-氯苯乙酮與醋酸鉀反應而製得(見稍後說明的參考實施例3)。此外,萘甲醛化合物包括1-萘甲醛及2-萘甲醛,且此等化合物係已知且可容易地取得。
反應溶劑之實例包括醇諸如甲醇、乙醇、丙醇、及異丙醇、乙腈、及四氫呋喃。
反應溫度係自50至80℃較佳;且反應時間係自1至10小時較佳。反應通常可於大氣壓力下進行。
在前述反應條件下生成之2-萘基-4-苯基咪唑化合物可藉由例如以下的分離操作取出。換言之,於反應完成後,經由過濾收集沉澱物,且使沉積物懸浮於甲醇中。接下來,將以萘甲醛化合物計自0.5至0.8莫耳倍數之量的氫硫化鈉逐步添加至此甲醇懸浮液,直至氫硫化鈉不再被消耗為止;將沉積的硫化銅濾除;將甲醇於真空中餾除;及以水沖洗殘留物,藉此可製得粗製期望材料之固體。此粗製材料可藉由再結晶操作或其類似操作純化。
在根據本發明之苯基萘基咪唑化合物中,經分類為2-萘基-4-苯基-5-甲基咪唑化合物(其中咪唑環的2-位次、4-位次及5-位次分別被萘基、苯基及甲基取代)之化合物,即2-(1-萘基)-4-苯基-5-甲基咪唑及2-(2-萘基)-4-苯基-5-甲基咪唑,可例如經由使萘甲醛化合物、1-苯基-1,2-丙二酮、及醋酸銨如以下之反應流程所示,於醋酸中加熱反應而合成得。
在如前述反應流程所示之反應中,以萘甲醛化合物計,1-苯基-1,2-丙二酮之使用量可在自0.8至1.5莫耳倍數的比例中較佳,及自0.9至1.1莫耳倍數更佳。以萘甲醛化合物計,醋酸銨之使用量可在自2至10莫耳倍數的比例中較佳,及自4至6莫耳倍數更佳。
使用於此反應中之萘甲醛化合物包括1-萘甲醛及2-萘甲醛,且此等化合物係與先前所說明者相同。
反應溫度係自80℃至回流溫度較佳;且反應時間係自1至10小時較佳。反應通常可於大氣壓力下進行。
在前述反應條件下生成之2-萘基-4-苯基-5-甲基咪唑化合物可藉由例如以下的分離操作取出。換言之,於反應完成後,將經由自反應混合物餾除乙酸而製得之反應混合物或殘留物及對其中所含之乙酸過量之鹼性試劑(例如,氫氧化鈉、碳酸鈉、及氨)溶解於水中並混合,藉此可使粗製期望材料沉澱。此粗製材料可藉由再結晶操作或其類似操作純化。
可將苯基萘基咪唑化合物溶解於適當載劑,諸如水或有機溶劑中,以形成表面處理劑。
苯基萘基咪唑化合物可以例如自0.01至10重量%,及以自0.1至5重量%較佳之比例,包含於表面處理劑中。當咪唑化合物之含量低於0.01重量%時,形成於銅表面上之化學層的膜厚度可能太薄,以致無法防止銅表面之氧化。另一方面,當其超過10重量%時,表面處理劑中之咪唑化合物可能會未被溶解,以致無法形成均勻的水溶液。
在將咪唑化合物溶解於水中(形成水溶液)時,可使用有機酸或無機酸作為酸,但可同時使用少量的有機溶劑。可使用之有機酸的代表性實例包括甲酸、乙酸、丙酸、丁酸、乙醛酸、丙酮酸、乙醯乙酸、4-戊酮酸、庚酸、辛酸、癸酸、月桂酸、羥乙酸、甘油酸、乳酸、丙烯酸、甲氧乙酸、乙氧乙酸、丙氧乙酸、丁氧乙酸、2-(2-甲氧乙氧)乙酸、2-[2-(2-乙氧乙氧)乙氧]乙酸、2-{2-[2-(2-乙氧乙氧)乙氧]乙氧}乙酸、甲氧丙酸、乙氧丙酸、丙氧丙酸、丁氧丙酸、苯甲酸、對硝基苯甲酸、對甲苯磺酸、水楊酸、苦味酸、草酸、琥珀酸、順丁烯二酸、反丁烯二酸、酒石酸、及己二酸;及無機酸之實例包括鹽酸、磷酸、硫酸、及硝酸。
以水溶液計,此一酸可以自0.1至50重量%,及以自1至30重量%較佳之比例添加。
此外,有機溶劑之實例包括低碳醇諸如甲醇、乙醇、及異丙醇、或丙酮、N,N-二甲基甲醯胺、及乙二醇及其類似物,其可與水自由地相混溶。
可於本發明之表面處理劑中加入金屬鹽。在使用銅化合物作為金屬鹽的情況中,可能可加速化學層在銅或銅合金之表面上的形成速率。此外,在使用鋅化合物作為金屬鹽的情況中,可能可進一步增進化學層的耐熱性。
銅化合物之代表性實例包括醋酸銅、氯化亞銅、氯化銅、溴化亞銅、溴化銅、碘化銅、氫氧化銅、磷酸銅、硫酸銅、及硝酸銅;及鋅化合物之代表性實例包括氧化鋅、甲酸鋅、醋酸鋅、草酸鋅、乳酸鋅、檸檬酸鋅、硫酸鋅、硝酸鋅、及磷酸鋅。此等金屬鹽可單獨或以其兩種或兩種以上之組合使用。金屬鹽可以自0.01至10重量%,及以自0.02至5重量%較佳之比例,添加於表面處理劑中。
在使用此一銅化合物或鋅化合物的情況中,可能希望經由在有機酸或無機酸之外再添加具有緩衝作用之物質,諸如氨、單乙醇胺、二乙醇胺、及三乙醇胺,而使溶液之pH穩定。
為進一步增進化學層之形成速率及薄膜之耐熱性,可將鹵素化合物添加於根據本發明之表面處理劑中。鹵素化合物之實例包括氟化鈉、氟化鉀、氟化銨、氯化鈉、氯化鉀、氯化銨、溴化鈉、溴化鉀、溴化銨、碘化鈉、碘化鉀、及碘化銨。此等鹵素化合物可單獨或以其兩種或兩種以上之組合使用。鹵素化合物可以自0.001至1重量%,及以自0.01至0.1重量%較佳之比例,添加於表面處理劑中。
關於使用根據本發明之表面處理劑處理銅或銅合金之表面的條件,表面處理劑之液體溫度可為例如自10至70℃,及接觸時間可為例如自1秒至10分鐘。接觸方法之實例包括蘸塗、噴塗、及塗布方法。
此外,於進行根據本發明之表面處理後,可經由利用熱塑性樹脂在化學層上形成雙重結構而進一步增進耐熱性。
換言之,於在銅或銅合金之表面上形成化學層後,可經由將具優異耐熱性之熱塑性樹脂(其可包括例如松香衍生物(例如,松香及松香酯)、萜烯樹脂衍生物(例如,萜烯樹脂及萜烯酚樹脂)、烴樹脂(例如,芳族烴樹脂及脂族烴樹脂)、或其混合物)溶解於溶劑(例如,甲苯、乙酸乙酯、及異丙醇)中,及使用例如輥塗機或其類似裝置,將溶液以例如自1至30微米之厚度均勻塗布於化學層上而形成化學層及熱塑性樹脂之雙重結構。
適用於實施本發明之焊料的實例不僅包括一般使用的錫鉛合金共熔焊料,並且包括無鉛焊料諸如Sn-Ag-Cu基、Sn-Ag-Bi基、Sn-Bi基、Sn-Ag-Bi-In基、Sn-Zn基、及Sn-Cu基焊料。
此外,本發明之焊接方法可適用於流動焊接方法及回焊(reflow)焊接方法。
流動焊接包括使印刷布線板於焊料槽中在熔融液態焊料之上移動,以焊接在電子零件與印刷布線板之間的接點。
相對地,回焊焊接包括預先將糊膏焊料根據電路圖案印刷於印刷布線板上,將電子零件安裝於其上,及加熱整個印刷布線板以使焊料熔融而完成焊接。
將參照實施例1至8將本發明之苯基萘基咪唑化合物的合成實施例明確說明於下,但不應將本發明解釋為受其所限制。附帶一提,使用於合成苯基萘基咪唑化合物之主要原料如下。
.苄脒鹽酸鹽(Tokyo Kasei Kogyo Co.,Ltd.製造之試劑).ω-溴-1-萘乙酮(利用如JP-A-9-286755中所述之方法製備得).ω-溴-2-萘乙酮(Tokyo Kasei Kogyo Co.,Ltd.製造之試劑).1-萘丙酮(利用如參考實施例1中所述之方法製備得).2-萘丙酮(利用如參考實施例2中所述之方法製備得).2-乙醯氧萘乙酮(利用如參考實施例3中所述之方法製備得).1-萘甲醛(Tokyo Kasei Kogyo Co.,Ltd.製造之試劑).2-萘甲醛(Tokyo Kasei Kogyo Co.,Ltd.製造之試劑).1-苯基-1,2-丙二酮(Tokyo Kasei Kogyo Co.,Ltd.製造之試劑)
在5至10℃下逐步將143.7克(1.08莫耳)之氯化鋁逐份添加至由92.6克(1.0莫耳)之丙醯氯及320毫升之1,2-二氯乙烷所組成之溶液中,及於添加完成後,將溫度提高至室溫,以製備丙醯氯.氯化鋁錯合物之1,2-二氯乙烷溶液。
在35至40℃下於1小時內將前述丙醯氯.氯化鋁錯合物之1,2-二氯乙烷溶液逐滴添加至由128.2克(1.0莫耳)之萘及300毫升之1,2-二氯乙烷所組成之溶液中。於添加完成後,將所得之混合液體於45至50℃下加熱2小時,及於冷卻至室溫後,將其倒入至冰水中。進一步加入200毫升之濃鹽酸,及將混合物攪拌並混合。利用氯仿以及1,2-二氯乙烷萃取於此反應混合物中生成之產物,將其於硫酸鎂上乾燥,並於真空中濃縮。將濃縮液體於真空中蒸餾而得145.3克(產率:79%,沸點:139至142℃/4毫米汞柱)之1-萘丙酮的淡黃色油。
將50.8克(0.33莫耳)之2-萘甲腈逐漸添加至由164克(0.5莫耳)之濃度3M之乙基溴化鎂之***溶液及120毫升之無水苯所組成之溶液中,及於停止產熱後,開始加熱。將約100毫升之主要包含***的餾出液餾除,加入100毫升苯,及將混合物於回流下加熱3小時。於加熱完成後,使反應混合物冷卻至室溫;加入由35克(0.654莫耳)之氯化銨及140毫升之水所組成之溶液;將水層移除;加入600毫升之6N鹽酸;及使混合物於回流下加熱4小時。於冷卻後,將水層移除;及將有機層以水洗滌,於硫酸鈉上乾燥,然後於真空中蒸發至乾而得57.3克(產率:94.2%)之2-萘丙酮的暗黃色固體。
將78.5克(0.80莫耳)之醋酸鉀、5.0克(0.08莫耳)之醋酸、及123.7克(0.80莫耳)之2-氯苯乙酮於500毫升乙醇中在回流下加熱6小時。於加熱完成後,使反應混合物冷卻至室溫,將沉積的氯化鉀濾除,及將乙醇於真空中餾除而得淡棕色油性物質。將此油性物質倒入1公升水中,及經由過濾收集沉澱固體並自甲醇再結晶而得113.1克(產率:79.3%)之2-乙醯氧苯乙酮之淡黃色固體。
將由31.3克(0.20莫耳)之苄脒鹽酸鹽、10.8克(0.20莫耳)之甲醇鈉、及150毫升之四氫呋喃所組成之懸浮液於回流下加熱1小時。於冷卻至25℃後,逐滴加入由49.8克(0.2莫耳)之ω-溴-1-萘乙酮及100毫升之四氫呋喃所組成之溶液,以致內部溫度不超過30℃。於添加完成後,加入10.8克(0.20莫耳)之甲醇鈉,及使混合物於回流下加熱1小時。接著使反應混合物冷卻至室溫,將不溶解的物質濾除,及使濾液於真空中蒸發至乾。將殘留固體以水及乙腈連續洗滌,然後乾燥而得粗製晶體之期望物料。使此粗製晶體自乙腈再結晶而得18.0克(產率:33.3%)之灰藍色晶體。
所得晶體之熔點、薄層層析術之Rf值、及NMR及質量光譜數據如下。
.熔點:167至169℃.TLC(矽膠,氯仿/乙酸乙酯=9/1),Rf=0.90.NMR(CD3
OD):δ7.3至8.4(m).MS m/z(%):270(M+,100)、167(56)、139(20)、117(5)、104(7)、89(6)由此等光譜數據,確認生成化合物為由以下化學式所表示之2-苯基-4-(1-萘基)咪唑。
將由31.3克(0.20莫耳)之苄脒鹽酸鹽、10.8克(0.20莫耳)之甲醇鈉、及150毫升之四氫呋喃所組成之懸浮液於回流下加熱1小時。於冷卻至20℃後,逐滴加入由49.8克(0.2莫耳)之ω-溴-2-萘乙酮及100毫升之四氫呋喃所組成之溶液,以致內部溫度不超過30℃。於添加完成後,加入10.8克(0.20莫耳)之甲醇鈉,及使混合物於回流下加熱1小時。接著使反應混合物冷卻至室溫,將不溶解的物質濾除,及使濾液於真空中蒸發至乾。將殘留固體以水及甲苯連續洗滌,然後乾燥而得粗製晶體之期望物料。使此粗製晶體自乙腈再結晶而得32.8克(產率:60.7%)之無色晶體。
所得晶體之熔點、薄層層析術之Rf值、及NMR及質量光譜數據如下。
.熔點:230至233℃.TLC(矽膠,氯仿/乙酸乙酯=9/1),Rf=0.33.NMR(CD3
OD):δ7.4至8.3(m).MS m/z(%):270(M+,100)、243(5)、166(11)、139(21)、117(10)、86(6)由此等光譜數據,確認生成化合物為由以下化學式所表示之2-苯基-4-(2-萘基)咪唑。
在50至55℃下將53.3克(0.334莫耳)之溴逐滴添加至由61.1克(0.332莫耳)之1-萘丙酮及180毫升之乙醇所組成之溶液中。於添加完成後,將乙醇於真空中餾除,及將所得之濃縮物溶解於130毫升之甲苯中,以碳酸氫鈉及氯化鈉之混合水溶液(150毫升×兩次)洗滌,然後於硫酸鈉上乾燥而得2-溴-1’-萘丙酮之甲苯溶液。
將由50.1克(0.32莫耳)之苄脒鹽酸鹽、133克(0.96莫耳)之碳酸鉀、及250毫升之四氫呋喃所組成之懸浮液於回流下加熱1小時,及將前述2-溴-1’-萘丙酮之甲苯溶液於50分鐘內逐滴加入。於添加完成後,在回流下加熱2小時。接著將反應混合物於真空中濃縮,將所得之濃縮物以200毫升之甲苯稀釋,及將溶液倒入至600毫升之水中。將混合物攪拌以使固體沉澱。經由過濾收集此固體,以甲苯及水連續洗滌,然後乾燥而得粗製晶體之期望物料。使此粗製晶體自DMF再結晶而得48.1克(產率:52.9%)之白色粉末。
所得粉末之熔點、薄層層析術之Rf值、及NMR及質量光譜數據如下。
.熔點:280至282℃.TLC(矽膠,丙酮),Rf=0.65.NMR(d6
-DMSO):δ2.27(s,3H)、7.38至8.27(m,12H).MS m/z(%):284(M+,100)、269(1)、215(4)、180(23)、166(4)、153(17)、139(10)、127(7)、104(10)、89(6)、77(10)、62(6)由此等光譜數據,確認生成化合物為由以下化學式所表示之2-苯基-4-(1-萘基)-5-甲基咪唑。
在50至55℃下將46.0克(0.288莫耳)之溴逐滴添加至由55.8克(0.303莫耳)之2-萘丙酮及250毫升之乙醇所組成之溶液中。於添加完成後,將乙醇於真空中餾除;及將所得之濃縮物溶解於130毫升之甲苯中,以碳酸氫鈉及氯化鈉之混合水溶液(200毫升×兩次)洗滌,然後於硫酸鈉上乾燥而得2-溴-2’-萘丙酮之甲苯溶液。
將由45.1克(0.288莫耳)之苄脒鹽酸鹽、119.4克(0.864莫耳)之碳酸鉀、及240毫升之四氫呋喃所組成之懸浮液於回流下加熱1小時,及將前述2-溴-2’-萘丙酮之甲苯溶液於40分鐘內逐滴加入。於添加完成後,繼續在回流下加熱2小時。接著將反應混合物於真空中濃縮,將所得之濃縮物以200毫升之甲苯稀釋,及將溶液倒入至600毫升之水中。將混合物攪拌以使固體沉澱。經由過濾收集此固體,以甲苯及水連續洗滌,然後乾燥而得粗製晶體之期望物料。使此粗製晶體自乙腈再結晶而得55.0克(產率:67.2%)之白色粉末。
所得粉末之熔點、薄層層析術之Rf值、及NMR及質量光譜數據如下。
.熔點:215至218℃.TLC(矽膠,丙酮),Rf=0.69.NMR(CDCl3
):δ2.56(s,3H)、7.34至8.03(m,12H).MS m/z(%):284(M+,100)、243(1)、215(2)、180(14)、153(12)、139(9)、127(4)、104(7)、89(5)、77(7)、63(5)由此等光譜數據,確認生成化合物為由以下化學式所表示之2-苯基-4-(2-萘基)-5-甲基咪唑。
在藉由水的冷卻下,將由70.3克(0.352莫耳)之單水合醋酸銅(II)及220克(3.2莫耳)之25%氨水所組成之溶液逐滴添加至由25.6克(0.160莫耳)之1-萘甲醛、29.4克(0.165莫耳)之2-乙醯氧苯乙酮、及300毫升之異丙醇所組成之溶液中,及接著將溫度於1小時內提高至60℃,及進一步於3小時內提高至78℃。於反應混合物冷卻後,經由過濾收集沉澱物,將其以水洗滌,然後乾燥。使所得之暗綠色粉末懸浮於甲醇中,加入8.1克(0.10莫耳)之70%氫硫化鈉,及將混合物於回流下加熱1小時。使此甲醇溶液冷卻,將黑色不溶解物質濾除,及將濾液於真空中蒸發至乾。
將殘留固體溶解於氯仿中及以水洗滌,將氯仿於真空中餾除,及使乾燥物料自乙腈再結晶而得12.1克(產率:28%)之乳白色粉末。
所得粉末之熔點、薄層層析術之Rf值、及NMR及質量光譜數據如下。
.熔點:198至202℃.TLC(矽膠,氯仿/乙酸乙酯=9/1),Rf=0.41.NMR(CD3
OD):δ7.0至8.4(m).MS m/z(%):270(M+,100)、241(3)、166(4)、139(10)、135(9)、127(7)、120(3)、116(5)、89(20)、77(4)、63(7)由此等光譜數據,確認生成化合物為由以下化學式所表示之2-(1-萘基)-4-苯基咪唑。
在藉由水的冷卻下,將由72.4克(0.363莫耳)之單水合醋酸銅(II)及230克(3.38莫耳)之25%氨水所組成之溶液逐滴添加至由26.1克(0.167莫耳)之2-萘甲醛、30.0克(0.168莫耳)之2-乙醯氧苯乙酮、及300毫升之異丙醇所組成之溶液中,及接著將溫度於1小時內提高至60℃,及進一步於3小時內提高至78℃。於反應混合物冷卻後,經由過濾收集沉澱物,將其以水洗滌,然後乾燥。使所得之暗綠色粉末懸浮於甲醇中,加入8.5克(0.11莫耳)之70%氫硫化鈉,及將混合物於回流下加熱1小時。使此甲醇溶液冷卻,將黑色不溶解物質濾除,及將濾液於真空中蒸發至乾。將殘留固體以水洗滌並溶解於丙酮中,加入草酸,及經由過濾收集沉澱的草酸鹽。將此草酸鹽懸浮於甲醇中,加入甲醇鈉以使期望物質釋出。將甲醇於真空中餾除,及將所得濃縮物以水洗滌及自甲醇再結晶而得6.1克(產率:13.5%)之淡黃色晶體。
所得晶體之熔點、薄層層析術之Rf值、及NMR及質量光譜數據如下。
.熔點:194至198℃.TLC(矽膠,氯仿/乙酸乙酯=9/1),Rf=0.57.NMR(d6
-DMSO):δ7.22至8.48(m).MS m/z(%):270(M+,100)、243(6)、215(3)、167(13)、153(6)、139(14)、127(9)、116(6)、89(25)、77(4)、63(9)由此等光譜數據,確認生成化合物為由以下化學式所表示之2-(2-萘基)-4-苯基咪唑。
將50.2克(0.34莫耳)之1-苯基-1,2-丙二酮、52.9克(0.34莫耳)之1-萘甲醛、及157克(2.04莫耳)之醋酸銨於250毫升醋酸中於回流下加熱3小時。將反應混合物於真空中濃縮,將大量稀氨水倒入所得之濃縮物中,及經由過濾收集沉澱固體並以水洗滌。將所得固體溶解於丙酮中,加入草酸,及經由過濾收集沉澱的草酸鹽。接著將收集得的草酸鹽溶解於甲醇中,加入甲醇鈉以使期望物質釋出,及將甲醇於真空中餾除。將殘留固體以水及正己烷連續洗滌而得30.8克(產率:32%)之乳白色晶體。
所得晶體之熔點、薄層層析術之Rf值、及NMR及質量光譜數據如下。
.熔點:80至85℃.TLC(矽膠,氯仿/乙酸乙酯=9/1),Rf=0.50.NMR(d6
-DMSO):δ2.53(s,3H)、7.14至8.02(m,12H).MS m/z(%):284(M+,100)、268(4)、241(2)、215(1)、180(2)、153(4)、142(6)、130(7)、103(12)、89(5)、77(7)、63(3)由此等光譜數據,確認生成化合物為由以下化學式所表示之2-(1-萘基)-4-苯基-5-甲基咪唑。
將24.5克(0.165莫耳)之1-苯基-1,2-丙二酮、25.8克(0.165莫耳)之2-萘甲醛、及76.5克(0.992莫耳)之醋酸銨於120毫升醋酸中於回流下加熱5小時。將反應混合物於真空中濃縮,將所得之濃縮物倒入至大量稀氨水中,及經由過濾收集沉澱固體並以水及乙腈連續洗滌而得22.7克(產率:48.2%)之淡黃棕色粉末。
所得粉末之熔點、薄層層析術之Rf值、及NMR及質量光譜數據如下。
.熔點:237至240℃.TLC(矽膠,氯仿/乙酸乙酯=9/1),Rf=0.57.NMR(CD3
OD):δ2.47(s,3H)、7.33至8.37(m,12H).MS m/z(%):284(M+,100)、243(3)、215(2)、180(5)、154(7)、142(9)、130(14)、103(13)、89(7)、77(8)、63(4)由此等光譜數據,確認生成化合物為由以下化學式所表示之2-(2-萘基)-4-苯基-5-甲基咪唑。
將參照實施例9至22及比較實施例1至7將根據本發明之使用苯基萘基咪唑化合物之表面處理劑、表面處理方法、焊接方法及印刷布線板的實例明確說明於下,但不應將本發明解釋為受其所限制。附帶一提,焊接試驗如下。
將由120毫米(長度)×150毫米(寬度)×1.6毫米(厚度)之玻璃環氧樹脂所製成且具有300個內徑0.80毫米之銅通孔的印刷布線板使用作為試件。將此試件脫脂,進行軟蝕刻(soft etching),然後以水洗滌。其後將試件於保持在指定液體溫度下之表面處理劑中浸泡指定的期間,以水洗滌,然後乾燥而於銅表面上形成厚度自約0.10至0.50微米之化學層。
使經表面處理之試件接受三個回焊加熱之循環,其中使用紅外回焊烘箱(商品名:MULTI-PRO-306,Vetronix Co.,Ltd.製造)最高溫度為240℃,及接著利用流動焊接裝置(輸送器速度:1.0米/分鐘)進行焊接。
所使用之焊料為具有63%錫及37%鉛(重量%)之組成物的錫鉛共熔焊料(商品名:H63A,Senju Metal Industry Co.,Ltd.製造),及使用於焊接之助焊劑為JS-64MSS(Koki Co.,Ltd.製造)。焊接溫度為240℃。
亦使用無鉛焊料以如錫鉛共熔焊料相同之方式焊接經如以上所處理之試件表面。所使用之焊料為具有96.5%錫、3.0%銀及0.5%銅(重量%)之組成物的無鉛焊料(商品名:H705「ECOSOLDER」,Senju Metal Industry Co.,Ltd.製造),及使用於焊接之助焊劑為JS-E-09(Koki Co.,Ltd.製造)。回焊加熱最高溫度為245℃,及焊接溫度亦為245℃。
對於經焊接之試件,將測量結果以其中之焊料填補至銅通孔之銅表面之銅通孔之數目相對於銅通孔之總數(300個孔洞)的比例(%)指示。
當銅表面上之焊料可濕性大時,熔融焊料會滲透各銅通孔內部,由此熔融焊料可容易地填補至通孔之上表面。更明確言之,如上表面經焊接之通孔的數目大,則判定焊料可濕性及對銅的焊接性優良。
將由50毫米(長度)×50毫米(寬度)×1.2毫米(厚度)之玻璃環氧樹脂所製成之印刷布線板使用作為試件。此印刷布線板具有將10件具0.80毫米導體寬度及20毫米長度之銅箔電路於寬度方向以1.0毫米間隔形成的電路圖案。將試件脫脂,進行軟蝕刻,然後以水洗滌。其後將試件於保持在指定液體溫度下之表面處理劑中浸泡指定的期間,以水洗滌,然後乾燥而於銅表面上形成厚度自約0.10至0.50微米之化學轉化膜。
使經表面處理之試件接受一個回焊加熱之循環,其中使用紅外回焊烘箱(商品名:MULTI-PRO-306,Vetronix Co.,Ltd.製造)最高溫度為240℃。其後使用1.2毫米孔隙直徑及150毫米厚度之金屬罩將錫鉛焊料糊印刷於銅電路之中心上,及在前述焊接條件下進行回焊加熱。所使用之錫鉛焊料糊為包含63%錫及37%鉛(重量%)之共熔焊料(商品名:OZ-63-330F-40-10,Senju Metal Industry Co.,Ltd.製造)。
亦使用無鉛焊料糊以如錫鉛焊料糊相同之方式焊接經如以上所處理之試件表面。所使用之無鉛焊料包含96.5%錫、3.0%銀及0.5%銅(重量%)(商品名:M705-221BM5-42-11,Senju Metal Industry Co.,Ltd.製造)。將於焊料糊印刷前後所達到之回焊加熱之最高溫度設為245℃。
測量潤濕且擴展於製得試件之銅電路上之焊料的長度(毫米)。
當長度較長時,將焊料可濕性及焊接性判定為優良。
將如於實施例2中合成得之作為苯基萘基咪唑化合物之2-苯基-4-(2-萘基)咪唑及作為酸之乳酸和正庚酸於去離子水中溶解成具有表1所述之組成物,及利用氨水將pH調整為3.2,因而製備得表面處理劑。
接下來,將印刷布線板之試件在控制於40℃溫度下之表面處理劑中浸泡240秒,以水洗滌,然後乾燥,因而測量焊料上流速率性質及焊料擴展性。此等試驗結果示於表1。
使用如表1所述之苯基萘基咪唑化合物、酸、金屬鹽及鹵素化合物,以與實施例9相同之方式製備具有如表1所述之組成物的表面處理劑,及在如表1所述之處理條件下進行表面處理。對所得之試件測量焊料上流速率性質及焊料擴展性。此等試驗結果示於表1。
附帶一提,使用作為酸之2-(2-甲氧乙氧)乙酸係SIGMA-ALDRICH製造之試劑。此外,關於2-[2-(2-乙氧乙氧)乙氧]乙酸及2-{2-[2-(2-乙氧乙氧)乙氧]乙氧}乙酸,使用根據Yukagaku
,32卷,118頁(1983)中所述之合成方法合成得之化合物。
使用如表2所述之咪唑化合物、酸、金屬鹽及鹵素化合物,以與實施例9相同之方式製備具有如表2所述之組成物的表面處理劑,及在如表2所述之處理條件下進行表面處理。對所得之試件測量焊料上流速率性質及焊料擴展性。此等試驗結果示於表2。
附帶一提,使用於比較實施例中之咪唑化合物如下。.2-十一基咪唑(商品名:C11Z,Shikoku Chemicals Corporation製造).2-苯基咪唑(商品名:2PZ,Shikoku Chemicals Corporation製造).2-苯基-4-甲基咪唑(商品名:2P4MZ,Shikoku Chemicals Corporation製造).2-壬基苯并咪唑(試劑,SIGMA-ALDRICH製造).2-(4-氯苯甲基)苯并咪唑(根據Science of Synthesis
,12卷,529(2002)中所述之方法合成得)
根據表1及表2所示之試驗結果,據認為在使根據本發明之表面處理劑與銅表面接觸而形成一化學層,然後再使用共熔焊料或無鉛焊料進行焊接的情況中,由於焊料上流速率性質及焊料擴展性顯著地增進,因而焊料可濕性於共熔焊接及無鉛焊接兩者中大大地改良。
本揭示內容係以2004年6月10日提出申請之日本專利申請案第2004-173150號、2004年7月27日提出申請之日本專利申請案第2004-218230號、及2005年4月27日提出申請之日本專利申請案第2005-128938號為基礎,並主張其之優先權,將前述專利之內容倂入本文為參考資料。
Claims (14)
- 一種苯基萘基咪唑化合物,其係選自由下列物質所組成之群:2-苯基-4-(1-萘基)-5-甲基咪唑,及2-苯基-4-(2-萘基)-5-甲基咪唑。
- 一種銅或銅合金之表面處理劑,其包含:載劑;比例為自0.01至10重量%之選自下列物質所組成之群之苯基萘基咪唑化合物:2-苯基-4-(1-萘基)-5-甲基咪唑,2苯基-4-(2-萘基)-5-甲基咪唑,2-苯基-4-(1-萘基)-咪唑,及2-苯基-4-(2-萘基)-咪唑;以及比例為自0.1至50重量%之有機酸或無機酸,其中該表面處理劑係為水溶液。
- 如申請專利範圍第2項之表面處理劑,其中,該載劑係為水或有機溶劑。
- 如申請專利範圍第2項之表面處理劑,其進一步包括金屬鹽。
- 如申請專利範圍第4項之表面處理劑,其中,該金屬鹽係選自由下列物質所組成之群之銅化合物:醋酸銅、氯化亞銅、氯化銅、溴化亞銅、溴化銅、碘化銅、氫氧化銅、磷酸銅、硫酸銅及硝酸銅。
- 如申請專利範圍第4項之表面處理劑,其中,該金屬 鹽係選自由下列物質所組成之群之鋅化合物:氧化鋅、甲酸鋅、醋酸鋅、草酸鋅、乳酸鋅、檸檬酸鋅、硫酸鋅、硝酸鋅及磷酸鋅。
- 如申請專利範圍第4項之表面處理劑,其中,該金屬鹽係以自0.01至10重量%之比例存在。
- 一種銅或銅合金之表面處理劑,其包含:載劑;比例為自0.01至10重量%之選自下列物質所組成之群之苯基萘基咪唑化合物:2-苯基-4-(1-萘基)-5-甲基咪唑,2-苯基-4-(2-萘基)-5-甲基咪唑,2-(1-萘基)-4-苯基咪唑,2-(2-萘基)-4-苯基咪唑,2-(1-萘基)-4-苯基-5-甲基咪唑,及2-(2-萘基)-4-苯基-5-甲基咪唑;以及鹵素化合物。
- 如申請專利範圍第8項之表面處理劑,其中,該鹵素化合物係選自由下列物質所組成之群:氟化鈉、氟化鉀、氟化銨、氯化鈉、氯化鉀、氯化銨、溴化鈉、溴化鉀、溴化銨、碘化鈉、碘化鉀及碘化銨。
- 如申請專利範圍第8項之表面處理劑,其中,該鹵素化合物係以自0.001至1重量%之比例存在。
- 一種銅或銅合金之表面處理方法,其包括使銅或銅合金之表面與表面處理劑接觸,該表面處理劑係包含: 載劑;比例為自0.01至10重量%之選自下列物質所組成之群之苯基萘基咪唑化合物:2-苯基-4-(1-萘基)咪唑,2-苯基-4-(2-萘基)咪唑,2-苯基-4-(1-萘基)-5-甲基咪唑,及2-苯基-4-(2-萘基)-5-甲基咪唑;以及比例為自0.1至50重量%之有機酸或無機酸,其中該表面處理劑係為水溶液。
- 一種焊接方法,其包括先使銅或銅合金之表面與表面處理劑接觸,然後再進行焊接;該表面處理劑係包含:載劑;比例為自0.01至10重量%之選自下列物質所組成之群之苯基萘基咪唑化合物:2-苯基-4-(1-萘基)咪唑,2-苯基-4-(2-萘基)咪唑,2-苯基-4-(1-萘基)-5-甲基咪唑,及2-苯基-4-(2-萘基)-5-甲基咪唑;以及比例為自0.1至50重量%之有機酸或無機酸,其中該表面處理劑係為水溶液。
- 一種印刷布線板,其包括構成銅電路部分之銅或銅合金,其中該銅或銅合金之表面經與一表面處理劑接觸而在其上形成一化學層,其中該表面處理劑包含: 載劑;比例為自0.01至10重量%之選自下列物質所組成之群之苯基萘基咪唑化合物:2-苯基-4-(1-萘基)咪唑,2-苯基-4-(2-萘基)咪唑,2-苯基-4-(1-萘基)-5-甲基咪唑,及2-苯基-4-(2-萘基)-5-甲基咪唑;以及比例為自0.1至50重量%之有機酸或無機酸,其中該表面處理劑係為水溶液。
- 一種苯基萘基咪唑化合物於銅或銅合金用之表面處理劑中之用途,該苯基萘基咪唑化合物係比例為自0.01至10重量%且選自下列物質所組成之群之:2-苯基-4-(1-萘基)咪唑,2-苯基-4-(2-萘基)咪唑,2-苯基-4-(1-萘基)-5-甲基咪唑,及2-苯基-4-(2-萘基)-5-甲基咪唑;該表面處理劑係進一步含有比例為自0.1至50重量%之有機酸或無機酸,其中該表面處理劑係為水溶液。
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JP2004218230A JP4194984B2 (ja) | 2004-07-27 | 2004-07-27 | フェニルナフチルイミダゾール化合物 |
JP2005128938A JP4694251B2 (ja) | 2004-06-10 | 2005-04-27 | 無鉛半田付け用の銅または銅合金の表面処理剤及びその利用 |
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EP (1) | EP1753728B1 (zh) |
KR (1) | KR101074640B1 (zh) |
BR (1) | BRPI0511916B1 (zh) |
HK (1) | HK1138577A1 (zh) |
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TWI790333B (zh) * | 2017-12-21 | 2023-01-21 | 日商東京應化工業股份有限公司 | 表面處理液、表面處理方法,及圖型倒塌之抑制方法 |
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JP4883996B2 (ja) * | 2005-05-24 | 2012-02-22 | 四国化成工業株式会社 | 水溶性プレフラックス及びその利用 |
GB0703172D0 (en) * | 2007-02-19 | 2007-03-28 | Pa Knowledge Ltd | Printed circuit boards |
MX2011001775A (es) | 2008-08-18 | 2011-06-20 | Semblant Global Ltd | Revestimiento de polimero de halo-hidrocarburo. |
JP5301218B2 (ja) * | 2008-08-25 | 2013-09-25 | 四国化成工業株式会社 | 銅または銅合金の表面処理剤及びその利用 |
US8995146B2 (en) | 2010-02-23 | 2015-03-31 | Semblant Limited | Electrical assembly and method |
US20170204089A1 (en) * | 2014-08-04 | 2017-07-20 | Drexel University | Novel compounds and methods of treating or ameliorating an il-1r-mediated disease or disorder using same |
GB201621177D0 (en) | 2016-12-13 | 2017-01-25 | Semblant Ltd | Protective coating |
JP6916731B2 (ja) | 2017-12-28 | 2021-08-11 | 東京応化工業株式会社 | 基板の撥水化方法、表面処理剤、及び基板表面を洗浄液により洗浄する際の有機パターン又は無機パターンの倒れを抑制する方法 |
CN111673078A (zh) * | 2020-05-14 | 2020-09-18 | 深圳第三代半导体研究院 | 一种微纳铜材料的抗氧化处理方法 |
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TW270944B (zh) | 1993-05-10 | 1996-02-21 | Shikoku Kakoki Co Ltd | |
JPH08183776A (ja) | 1994-12-28 | 1996-07-16 | Hideaki Yamaguchi | 金属の表面保護剤ならびにそれを用いた製造方法 |
JPH10280162A (ja) | 1997-04-07 | 1998-10-20 | Hideaki Yamaguchi | プリント配線板の表面保護剤および表面保護膜の形成方法。 |
CA2294898A1 (en) | 1997-07-03 | 1999-01-14 | Neurogen Corporation | Certain diarylimidazole derivatives; a new class of npy specific ligands |
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JP2005068530A (ja) | 2003-08-28 | 2005-03-17 | Tamura Kaken Co Ltd | 表面処理剤、プリント回路基板およびプリント回路基板の金属の表面処理方法 |
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US20120199385A1 (en) | 2012-08-09 |
US20070246134A1 (en) | 2007-10-25 |
KR20070019764A (ko) | 2007-02-15 |
EP1753728A1 (en) | 2007-02-21 |
US8183386B2 (en) | 2012-05-22 |
BRPI0511916A (pt) | 2008-01-15 |
BRPI0511916B1 (pt) | 2014-10-14 |
TW200604379A (en) | 2006-02-01 |
US8378116B2 (en) | 2013-02-19 |
HK1138577A1 (en) | 2010-08-27 |
MY149388A (en) | 2013-08-30 |
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