JP6141664B2 - めっき浴および方法 - Google Patents
めっき浴および方法 Download PDFInfo
- Publication number
- JP6141664B2 JP6141664B2 JP2013067757A JP2013067757A JP6141664B2 JP 6141664 B2 JP6141664 B2 JP 6141664B2 JP 2013067757 A JP2013067757 A JP 2013067757A JP 2013067757 A JP2013067757 A JP 2013067757A JP 6141664 B2 JP6141664 B2 JP 6141664B2
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- JP
- Japan
- Prior art keywords
- silver
- alkyl
- tin
- acid
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000007747 plating Methods 0.000 title description 38
- 238000000034 method Methods 0.000 title description 29
- 239000000203 mixture Substances 0.000 claims description 67
- -1 silver ions Chemical class 0.000 claims description 64
- 238000009713 electroplating Methods 0.000 claims description 63
- 239000004332 silver Substances 0.000 claims description 57
- 229910052709 silver Inorganic materials 0.000 claims description 56
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 50
- 239000000758 substrate Substances 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- QCEUXSAXTBNJGO-UHFFFAOYSA-N [Ag].[Sn] Chemical compound [Ag].[Sn] QCEUXSAXTBNJGO-UHFFFAOYSA-N 0.000 claims description 24
- 239000003792 electrolyte Substances 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 238000000151 deposition Methods 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910001432 tin ion Inorganic materials 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 45
- 229910001316 Ag alloy Inorganic materials 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 30
- 235000012431 wafers Nutrition 0.000 description 28
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 23
- 239000002184 metal Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- 239000004065 semiconductor Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 239000011135 tin Substances 0.000 description 21
- 229910052718 tin Inorganic materials 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 19
- 229910000679 solder Inorganic materials 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 239000010949 copper Substances 0.000 description 13
- 229940098779 methanesulfonic acid Drugs 0.000 description 13
- 150000003568 thioethers Chemical class 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- 229910052802 copper Inorganic materials 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 238000005275 alloying Methods 0.000 description 11
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 10
- 229910020836 Sn-Ag Inorganic materials 0.000 description 10
- 229910020988 Sn—Ag Inorganic materials 0.000 description 10
- 229910045601 alloy Inorganic materials 0.000 description 10
- 239000000956 alloy Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- LTXRPFGDTYMYDS-UHFFFAOYSA-N 3-(3-hydroxypropylsulfanylmethylsulfanyl)propan-1-ol Chemical compound OCCCSCSCCCO LTXRPFGDTYMYDS-UHFFFAOYSA-N 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- DAGVPUJNMLIIMC-UHFFFAOYSA-N 2-[2-(2-sulfoethylsulfanyl)ethylsulfanyl]ethanesulfonic acid Chemical compound OS(=O)(=O)CCSCCSCCS(O)(=O)=O DAGVPUJNMLIIMC-UHFFFAOYSA-N 0.000 description 7
- 239000008139 complexing agent Substances 0.000 description 7
- NYOWZTOMFCVCGL-UHFFFAOYSA-N 2-(1,2-dicarboxyethylsulfanylmethylsulfanyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)SCSC(C(O)=O)CC(O)=O NYOWZTOMFCVCGL-UHFFFAOYSA-N 0.000 description 6
- GBZDOXLAUOJYPB-UHFFFAOYSA-N 3-[2-(3-hydroxypropylsulfanyl)ethylsulfanyl]propan-1-ol Chemical compound OCCCSCCSCCCO GBZDOXLAUOJYPB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000002671 adjuvant Substances 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- CZEVAMMETWVBOD-UHFFFAOYSA-N 2-(carboxymethylsulfanylmethylsulfanyl)acetic acid Chemical compound OC(=O)CSCSCC(O)=O CZEVAMMETWVBOD-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- 229940100890 silver compound Drugs 0.000 description 5
- 150000003379 silver compounds Chemical class 0.000 description 5
- QFEGZYANALYACQ-UHFFFAOYSA-N 2-[3-(carboxymethylsulfanyl)propylsulfanyl]acetic acid Chemical compound OC(=O)CSCCCSCC(O)=O QFEGZYANALYACQ-UHFFFAOYSA-N 0.000 description 4
- UZRYZOUNEIPKQQ-UHFFFAOYSA-N 3-[2-(3-sulfopropylsulfanyl)ethylsulfanyl]propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCSCCSCCCS(O)(=O)=O UZRYZOUNEIPKQQ-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 4
- PQIJHIWFHSVPMH-UHFFFAOYSA-N [Cu].[Ag].[Sn] Chemical compound [Cu].[Ag].[Sn] PQIJHIWFHSVPMH-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 229930003944 flavone Natural products 0.000 description 4
- 235000011949 flavones Nutrition 0.000 description 4
- 229920002120 photoresistant polymer Polymers 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 150000003606 tin compounds Chemical class 0.000 description 4
- 229910000969 tin-silver-copper Inorganic materials 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 4
- 125000006526 (C1-C2) alkyl group Chemical class 0.000 description 3
- CCQMORVULNZXIA-UHFFFAOYSA-N 2-[2-(carboxymethylsulfanyl)ethylsulfanyl]acetic acid Chemical compound OC(=O)CSCCSCC(O)=O CCQMORVULNZXIA-UHFFFAOYSA-N 0.000 description 3
- GNMCEWMUFTZBKH-UHFFFAOYSA-N 3-[2-(2-carboxyethylsulfanyl)ethylsulfanyl]propanoic acid Chemical compound OC(=O)CCSCCSCCC(O)=O GNMCEWMUFTZBKH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229910001128 Sn alloy Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005229 chemical vapour deposition Methods 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
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910001092 metal group alloy Inorganic materials 0.000 description 3
- AICMYQIGFPHNCY-UHFFFAOYSA-J methanesulfonate;tin(4+) Chemical compound [Sn+4].CS([O-])(=O)=O.CS([O-])(=O)=O.CS([O-])(=O)=O.CS([O-])(=O)=O AICMYQIGFPHNCY-UHFFFAOYSA-J 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 2
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 2
- XMVGTSVHEMLOIS-UHFFFAOYSA-N 2-[3-(2-sulfoethylsulfanyl)propylsulfanyl]ethanesulfonic acid Chemical compound OS(=O)(=O)CCSCCCSCCS(O)(=O)=O XMVGTSVHEMLOIS-UHFFFAOYSA-N 0.000 description 2
- RNKSNQNKTRGJSZ-UHFFFAOYSA-N 3,5,6,7,8-pentahydroxy-2-phenylchromen-4-one Chemical class OC=1C(O)=C(O)C(O)=C(C(C=2O)=O)C=1OC=2C1=CC=CC=C1 RNKSNQNKTRGJSZ-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- RYKLZUPYJFFNRR-UHFFFAOYSA-N 3-hydroxypiperidin-2-one Chemical compound OC1CCCNC1=O RYKLZUPYJFFNRR-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- SHLSSLVZXJBVHE-UHFFFAOYSA-N 3-sulfanylpropan-1-ol Chemical compound OCCCS SHLSSLVZXJBVHE-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 description 2
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 2
- JWVAUCBYEDDGAD-UHFFFAOYSA-N bismuth tin Chemical compound [Sn].[Bi] JWVAUCBYEDDGAD-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- RTIXKCRFFJGDFG-UHFFFAOYSA-N chrysin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 RTIXKCRFFJGDFG-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229940093503 ethyl maltol Drugs 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- XHEFDIBZLJXQHF-UHFFFAOYSA-N fisetin Chemical compound C=1C(O)=CC=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 XHEFDIBZLJXQHF-UHFFFAOYSA-N 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- LQBJWKCYZGMFEV-UHFFFAOYSA-N lead tin Chemical compound [Sn].[Pb] LQBJWKCYZGMFEV-UHFFFAOYSA-N 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000002161 passivation Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000005360 phosphosilicate glass Substances 0.000 description 2
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HNFOAHXBHLWKNF-UHFFFAOYSA-M sodium;2-bromoethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCBr HNFOAHXBHLWKNF-UHFFFAOYSA-M 0.000 description 2
- LNZDAVYFINUYOH-UHFFFAOYSA-M sodium;3-bromopropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCBr LNZDAVYFINUYOH-UHFFFAOYSA-M 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
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- 238000001228 spectrum Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
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- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/46—Electroplating: Baths therefor from solutions of silver
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/30—Electroplating: Baths therefor from solutions of tin
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/56—Electroplating: Baths therefor from solutions of alloys
- C25D3/60—Electroplating: Baths therefor from solutions of alloys containing more than 50% by weight of tin
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/56—Electroplating: Baths therefor from solutions of alloys
- C25D3/64—Electroplating: Baths therefor from solutions of alloys containing more than 50% by weight of silver
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
- C23C18/48—Coating with alloys
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- H01L2224/034—Manufacturing methods by blanket deposition of the material of the bonding area
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Description
Y1−(CR1R2)m−S−(CR3R4)x−S−(CR5R6)n−Y2
(式中、Y1およびY2は独立してCO2H、SO3H、PO3H2、CONR7R8およびOHから選択され;各R1、R2、R5およびR6は独立してH、(C1−C6)アルキル、CO2Hおよびヒドロキシ置換(C1−C6)アルキルから選択され;各R3およびR4は独立してHおよび(C1−C6)アルキルから選択され;m=1〜6;n=1〜6;R7およびR8は独立してHおよび(C1−C3)アルキルから選択され;並びに、x=1〜6であり;ただし、Y1=OHである場合にはm=3であり;ただし、Y2=OHである場合にはn=3であり;ただし、R1、R2、R5およびR6のいずれかがヒドロキシ置換(C1−C6)アルキルである場合には、このヒドロキシ基は硫黄原子に対して少なくともガンマである炭素原子に結合されている)のスルフィド化合物を含む電気めっき組成物を提供する。この電気めっき組成物は1種以上の合金形成金属および1種以上のアジュバントをさらに含むことができる。
Y1−(CR1R2)m−S−(CR3R4)x−S−(CR5R6)n−Y2
(式中、Y1およびY2は独立してCO2H、SO3H、PO3H2、CONR7R8およびOHから選択され;各R1、R2、R5およびR6は独立してH、(C1−C6)アルキル、CO2Hおよびヒドロキシ置換(C1−C6)アルキルから選択され;各R3およびR4は独立してHおよび(C1−C6)アルキルから選択され;m=1〜6;n=1〜6;R7およびR8は独立してHおよび(C1−C3)アルキルから選択され;並びに、x=1〜6であり;ただし、Y1=OHである場合にはm=3であり;ただし、Y2=OHである場合にはn=3であり;ただし、R1、R2、R5およびR6のいずれかがヒドロキシ置換(C1−C6)アルキルである場合には、このヒドロキシ基は硫黄原子に対して少なくともガンマである炭素原子に結合されている)のスルフィド化合物を含む電気めっき組成物を基体と接触させ:並びに一定期間にわたって電位を適用して、前記基体上にスズ−銀含有層を析出させることを含む、基体上に銀または銀合金層を析出させる方法も提供される。
Y1−(CR1R2)m−S−(CR3R4)x−S−(CR5R6)n−Y2
(式中、Y1およびY2は独立してCO2H、SO3H、PO3H2、CONR7R8およびOHから選択され;各R1、R2、R5およびR6は独立してH、(C1−C6)アルキル、CO2Hおよびヒドロキシ置換(C1−C6)アルキルから選択され;各R3およびR4は独立してHおよび(C1−C6)アルキルから選択され;m=1〜6;n=1〜6;R7およびR8は独立してHおよび(C1−C3)アルキルから選択され;並びに、x=1〜6であり;ただし、Y1=OHである場合にはm=3であり;ただし、Y2=OHである場合にはn=3であり;ただし、R1、R2、R5およびR6のいずれかがヒドロキシ置換(C1−C6)アルキルである場合には、このヒドロキシ基は硫黄原子に対して少なくともガンマである炭素原子に結合されている)のスルフィド化合物の使用が電気めっき浴の安定性を向上させることが驚くべきことに認められた。このスルフィド化合物は銀電気めっき浴中で錯化剤(complexer)として機能する。
Y1−(CR1R2)m−S−(CR3R4)x−S−(CR5R6)n−Y2
(式中、Y1およびY2は独立してCO2H、SO3H、PO3H2、CONR7R8およびOHから選択され;各R1、R2、R5およびR6は独立してH、(C1−C6)アルキル、CO2Hおよびヒドロキシ置換(C1−C6)アルキルから選択され;各R3およびR4は独立してHおよび(C1−C6)アルキルから選択され;m=1〜6;n=1〜6;R7およびR8は独立してHおよび(C1−C3)アルキルから選択され;並びに、x=1〜6であり;ただし、Y1=OHである場合にはm=3であり;ただし、Y2=OHである場合にはn=3であり;ただし、R1、R2、R5およびR6のいずれかがヒドロキシ置換(C1−C6)アルキルである場合には、このヒドロキシ基は硫黄原子に対して少なくともガンマである炭素原子に結合されている)の1種以上のスルフィド化合物を含む。語句「このヒドロキシ基は硫黄原子に対して少なくともガンマで炭素原子に結合されている」とは、硫黄原子から3炭素以上離れているヒドロキシル基をいう。すなわち、このヒドロキシル基は硫黄原子から3、4、5、6、7、8、9または10炭素離れていてよく、好ましくは硫黄原子から3、4、5、6、7または8炭素離れていてよく、より好ましくは硫黄原子から3、4、5または6炭素離れていてよく、並びに最も好ましくは硫黄原子から3炭素離れていてよい。好ましくは、各R1、R2、R5およびR6は独立してH、(C1−C4)アルキル、CO2Hおよびヒドロキシ置換(C1−C4)アルキルから選択され、より好ましくはH、(C1−C4)アルキル、およびヒドロキシ置換(C1−C2)アルキルから選択され、さらにより好ましくはH、(C1−C2)アルキル、およびヒドロキシ置換(C1−C2)アルキルから選択され、並びにさらにより好ましくはH、およびヒドロキシ置換(C1−C2)アルキルから選択される。R7およびR8は独立して好ましくはH、メチルおよびエチルから選択され、より好ましくはHおよびメチルから選択される。好ましくはR7=R8であり、より好ましくはR7=R8=Hである。Y1およびY2は独立してCO2H、SO3H、PO3H2、およびOHから選択されるのが好ましく、CO2H、SO3H、およびPO3H2から選択されるのがより好ましく、CO2H、およびSO3Hから選択されるのがさらにより好ましい。あるいは、Y1およびY2は独立してCO2H、SO3H、およびOHから選択される。m=1〜4であるのが好ましく、1〜3がより好ましい。好ましくはn=1〜4であり、より好ましくはn=1〜3である。x=1〜4であるのが好ましく、1〜3であるのがより好ましく、1〜2であるのがさらにより好ましい。Y1とY2とは好ましくは同じであり、すなわち、好ましくはY1=Y2である。Y1およびY2は独立してCO2H、SO3H、およびOHから選択され;各R1、R2、R5およびR6は独立してH、(C1−C3)アルキル、およびヒドロキシ置換(C1−C3)アルキルから選択され;各R3およびR4は独立してHおよび(C1−C3)アルキルから選択され;m=1〜4;n=1〜4;並びに、x=1〜4であるのがさらに好ましい。典型的なヒドロキシ置換(C1−C6)アルキル基には、2−ヒドロキシ−1−エチル、2−ヒドロキシ−1−プロピル、3−ヒドロキシ−2−ブチル、2−ヒドロキシ−2−プロピル、2−ヒドロキシ−2−メチル−2−プロピル、2−ヒドロキシ−1−ブチル、2−ヒドロキシ−2−メチル−2−ブチル、1−ヒドロキシ−2−ブチル、2−ヒドロキシ−2−メチル−1−プロピル、3−ヒドロキシ−2−ブチル、および2−ヒドロキシメチル−2−ブチルが挙げられる。
3,3’−(エタン−1,2−ジイルビス(スルファンジイル))ジプロパンアミド(化合物1):
四ホウ酸ナトリウム(1.20g、5.95mmol)がDI水(150mL)に溶解させられた。1,2−エタンジチオール(5.00mL、59.4mmol)が添加され、次いでアクリルアミド(9.31g、130mmol)が添加され、そして室温で2時間にわたって攪拌されて白色スラリーを得た。固体は濾別され、水で洗浄され、そして真空下で乾燥させられて、13.1g(93.2%)の化合物1を白色固体として得た。1H NMR(500MHz、d6−DMSO)δ7.33(s,2H)、6.82(s,2H)、3.37(s,4H)、2.69(t,J=7.2Hz4H)、2.32(t,J=7.3Hz,4H)。13C NMR(126MHz,d6−DMSO)δ172.68、35.69、31.35、26.92。
3,3’−(エタン−1,2−ジイルビス(スルファンジイル))ジプロパン酸(化合物2):
アクリルアミドがアクリル酸メチルに変えられてジエステル化合物である3,3’−(エタン−1,2−ジイルビス(スルファンジイル))ジプロパン酸ジメチルを形成したこと以外は実施例1の手順が概して繰り返された。このジエステル(5.00g、18.8mmol)は2NのHCl(50mL)中で2時間にわたって還流加熱され、次いで一晩室温で冷却され、白色沈殿を得た。この固体は濾別され、水で洗浄され、そして真空下で乾燥させられて、4.26g(95.2%)の化合物2を白色固体として得た。1H NMR(500MHz、d6−DMSO)δ12.10(s,2H)、2.61(t,J=7.1Hz,4H)、2.60(s,4H)、2.40(t,J=7.1Hz,4H)。13C NMR(126MHz,d6−DMSO)δ172.98、31.70、31.47、26.44。
2,2’−(エタン−1,2−ジイルビス(スルファンジイル))ジ酢酸(化合物3):
1,2−エタンジチオール(5.00mL、59.4mmol)がCH2Cl2(100mL)に溶解させられ、そしてEt3N(15.0g、149mmol)が添加された。次いで、この混合物は0℃まで冷却され、ブロモメチルアセタート(19.1g、125mmol)のCH2Cl2(25mL)中の溶液がゆっくりと滴下添加された。この添加が完了した後で、この反応混合物は周囲温度まで暖められ、そして2時間にわたって攪拌された。有機層が0.5MのHCl(100mL)、NaHCO3飽和水溶液、ブラインで洗浄され、そしてNa2SO4で乾燥させられ、次いで濃縮されて、12.9g(90.8%)のジエステル化合物である2,2’−(エタン−1,2−ジイルビス(スルファンジイル))ジ酢酸ジメチルを透明オイルとして得た。1H NMR(500MHz、CDCl3)δ3.74(s,6H)、3.28(s,4H)、2.89(s,4H)。13C NMR(126MHz,CDCl3)δ170.53、52.31、33.15、31.87。
2,2’−(エタン−1,2−ジイルビス(スルファンジイル))ジ酢酸ジメチル(7.00g、29.4mmol)が2時間にわたって2NのHCl(50mL)中で還流加熱された。この混合物を室温まで冷却して透明溶液を得て、この透明溶液は真空下で濃縮乾固させられて、白色固体として5.98g(96.8%)の化合物3を得た。1H NMR(400MHz、D2O)δ3.47(s,4H)、2.95(s,4H)。13C NMR(101MHz,D2O)δ174.61、33.28、31.39。
2,2’−(エタン−1,2−ジイルビス(スルファンジイル))ジエタンスルホン酸(化合物4):
2−ブロモエチルスルホン酸ナトリウム塩(25.6g、125mmol)およびナトリウムメトキシド(8.03g、149mmol)のEtOH(350mL)中の溶液に、0℃で、EtOH(25mL)中の1,2−エタンジチオール(5.00mL、59.4mmol)の溶液が滴下添加された。この反応混合物が室温まで暖められ、次いで48時間にわたって還流加熱された。次いで、この混合物は室温まで冷却され、次いで2NのHClでpH1〜2まで酸性化された。得られた懸濁物は75℃まで加熱され、そして透明な溶液が得られるまで水が小分けにしてゆっくりと添加された。次いで、この反応混合物は室温まで冷却され、次いで5℃まで冷却された。得られた白色沈殿は濾別され、冷EtOHで洗浄され、そして乾燥させられて、11.9g(64.6%)の化合物4を白色粉体として得た。1H NMR(500MHz、D2O)δ3.27(t,J=9.3,6.4Hz,4H)、3.06−2.99(m,4H)、2.98(s,4H)。13C NMR(126MHz,D2O)δ51.11、31.09、25.58。
3,3’−(エタン−1,2−ジイルビス(スルファンジイル))ビス(プロパン−1−スルホン酸)(化合物5):
3−ブロモプロパンスルホン酸ナトリウム塩(24.7g、110mmol)およびナトリウムメトキシド(7.06g、131mmol)のEtOH(300mL)中の溶液に、周囲温度で、エタノール(25mL)中の1,2−エタンジチオール(4.4mL、52.3mmol)が滴下添加された。室温で1時間攪拌し、次いで一晩還流加熱された。室温まで冷却され、2NのHClでpH1〜2まで酸性化された。得られた懸濁物は75℃まで加熱され、そして透明な溶液が得られるまで水が小分けにしてゆっくりと添加された。室温まで冷却され、次いで5℃まで冷却された。得られた白色沈殿は濾別され、冷EtOHで洗浄され、そして乾燥させられて、11.9g(67.4%)を白色粉体として得た。1H NMR(400MHz、D2O)δ3.10(t,J=7.2Hz,4H)、2.92(s,4H)、2.82(t,J=7.2Hz,4H)、2.11(m,4H)。13C NMR(101MHz,D2O)δ52.26、33.38、32.27、26.80。
3,3’−[1,2−エタンジイルビス(チオ)]ビス−1−プロパノール(化合物6):
3−クロロプロパノール(56.5g、0.569mol)のアセトニトリル(50mL)中の溶液が、1,2−ジチオエタン(25.0g、0.265mol)および炭酸ナトリウム(70.3g、0.663mol)のアセトニトリル(100mL)中の溶液にゆっくりと滴下添加された。この添加が完了した後で、この反応混合物は3時間にわたって還流加熱され、次いで周囲温度まで冷却された。DI水(100mL)が添加されてこの固体を溶解させ、そして得られた溶液がEtOAc(200mL)で抽出された。有機層が水(100mL)およびブライン(50mL)で洗浄され、次いでNa2SO4で乾燥させられた。濃縮乾固させられ、次いでEtOAcから再結晶化させることによって、18.2gの化合物6(33%)を白色固体として得た。1H NMR(CDCl3)δ3.76(t,J=6.0Hz,4H)、2.76(s,1H)、2.68(t,J=7.1Hz,4H),1.97bs,2H)、1.86(dd,J=9.6,3.6Hz,4H)。13C NMR(CDCl3)δ61.50、32.01、32.05、28.79。
3,3’−(メチレンビス(スルファンジイル))ジプロパノール(化合物7):
凝縮器および添加漏斗を備えた丸底フラスコに、3−メルカプトプロパノール(5.20mL、60.5mmol)および粉砕された水酸化ナトリウム(2.42g、60.5mmol)が入れられた。このフラスコは氷浴中に配置され、そしてフラスコ内容物は攪拌させられた。反応混合物を20℃未満に維持しつつ、ジブロモメタン(20.8mL、30.2mmol)が添加漏斗によって滴下添加された。添加完了後に、この反応混合物は室温まで暖められ、次いで一晩還流加熱された。この時間中に、色が黄色に変わった。固体残留物に、この粗生成物を溶解しない幾分かのジクロロメタンが添加された。DI水が添加され、そしてこの内容物の全てが溶液になった。この反応混合物は水およびジブロモメタンを除去するように減圧下で濃縮させられた。この粗生成物は再びDI水に溶解させられ、そしてシリンジフィルタを通して濾過され、そして濃縮された。この生成物は出発3−メルカプトプロパノールを除去するために80℃で高真空下に置かれた。これは除去されず、よって追加の2ペレットのNaOHが粉砕されそして攪拌して粗生成物に入れられた。約300μLのジブロモメタンが入れられて攪拌された。この反応容器は手作業で攪拌させられ、かつ全てのものを一緒に溶融させるために80℃で一晩油浴中に配置された。この反応混合物は濃縮され、そしてジブロモメタンが除去された。この生成物は高真空下に配置され、6.21グラムの化合物7を薄黄色固体として提供した。1H NMR(500MHz,D2O)δ4.14(d,J=19.4Hz,2H)、4.01(t,J=6.4Hz,4H)、3.07(t,J=7.3Hz,4H)、2.24−2.12(m,4H)。13C NMR(126MHz,D2O)δ60.92、34.75、31.42、27.79。
2,2’−(メチレンビス(スルファンジイル))ジ酢酸(化合物8):
丸底フラスコに、ホルムアルデヒド(10.0mL、124mmol)およびチオグリコール酸(18.9g、206mmol)が入れられた。この混合物は攪拌され、そして濃塩酸(7mL)が滴下添加された。この反応混合物は50℃で1時間にわたって、次いで110℃で一晩攪拌された。この反応混合物は室温まで冷却され、次いで3日間冷蔵庫に貯蔵された。この時間中に、白色固体が生じた。この固体は濾過によって分離され、次いで水から再結晶させられて、8.16g(26.22mmol、32.0%)の9を白色固体として得た。1H NMR(500MHz,d6−DMSO)δ3.39(s,4H)、3.94(s,2H)。13C NMR(126MHz,d6−DMSO)δ32.65、37.01、137.76。
2,2’−(メチレンビス(スルファンジイル))ジコハク酸(化合物9):
丸底フラスコに、ホルムアルデヒド(7.95mL、98.3mmol)およびメルカプトコハク酸(24.6g、163.8mmol)が入れられた。この混合物は攪拌され、そして濃塩酸(7mL)が滴下添加された。この反応混合物は50℃で1時間にわたって、次いで110℃で一晩攪拌された。この反応混合物は室温まで冷却され、次いで3日間冷蔵庫に貯蔵された。この時間中に、白色固体が生じた。この固体は濾過によって分離され、次いで水から再結晶させられて、8.16g(26.22mmol、32.0%)の9を白色固体として得た。1H NMR(500MHz,d6−DMSO)δ4.01−3.97(m,2H)、3.71(ddd,J=12.4、6.2、3.5Hz,2H)、2.81−2.71(m,2H)、2.64−2.55(m,2H)。13C NMR(126MHz,d6−DMSO)δ172.73、172.04、40.77、36.12、34.84。
2,2’−(プロパン−1,3−ジイルビス(スルファンジイル))ジ酢酸(化合物10):
1,3−プロパンジチオール(5.00mL、49.9mmol)がCH2Cl2(100mL)に溶解させられ、そしてトリエチルアミン(17.4mL、125mmol)が添加された。この反応混合物は0℃に冷却され、そしてブロモ酢酸メチル(9.85mL、105mmol)の塩化メチレン(50mL)中の溶液が滴下添加された。この添加が完了した後で、この反応混合物は室温まで暖められそして2時間にわたって攪拌された。有機相は0.5MのHCl(100mL)、飽和NaHCO3水溶液、ブラインで洗浄させられ、そしてNa2SO4で乾燥させられた。溝付きろ紙を用いてこの有機相が濾過され、そして減圧下で濃縮されて、11.3g(44.9mmol、90.0%)の2,2’−(プロパン−1,3−ジイルビス(スルファンジイル))ジ酢酸ジメチルである薄黄色オイルを得た。1H NMR(400MHz,CD2Cl2)δ3.65(s,6H)、3.18(s,4H)、2.67(t,J=7.2Hz,4H)、1.83(p,J=7.1Hz,2H)。13C NMR(101MHz,CD2Cl2)δ171.09、52.58、33.73、31.68、28.62。
2,2’−(プロパン−1,3−ジイルビス(スルファンジイル))ジ酢酸ジメチル(11.3g、44.9mmol)が2時間にわたって2NのHCl(50mL)中で還流加熱された。完了後に、この反応混合物は室温まで冷却された。この反応混合物は減圧下で濃縮乾固させられて、灰白色固体(32.5mmol、72.4%)として7.29gの化合物10を得た。1H NMR(400MHz、CD2Cl2)δ11.45(s,2H)、3.28(s,4H)、2.82−2.69(m,4H)、1.92(p,J=7.2Hz,2H)。13C NMR(101MHz,CD2Cl2)δ177.36、33.93、31.90、28.63。
2,2’−(プロパン−1,3−ジイルビス(スルファンジイル))ジエチルスルホナート(化合物11):
2−ブロモエチルスルホン酸ナトリウム塩(21.0g、100mmol)およびナトリウムメトキシド(5.40g、100mmol)のエタノール(350mL)中の溶液に、0℃で、1,3−プロパンジチオール(5.00mL、50.0mmol)のEtOH(25.0mL)中の溶液が滴下添加された。この反応混合物は周囲温度まで暖められ、次いで48時間にわたって還流加熱された。この反応混合物は室温まで冷却され、次いで2NのHClを用いてpH1〜2まで酸性化された。得られた懸濁物は75℃まで加熱され、そして透明な薄黄色溶液が得られるまで水が少しづつに分けてゆっくりと添加された。この溶液は室温に平衡化され、次いで5℃に冷却された。得られた白色沈殿は濾別され、冷EtOHで洗浄させられ、乾燥させられた。エタノールからの再結晶化によって白色固体として(3.99g、24.8%)化合物11を得た。1H NMR(400MHz,D2O)δ3.34−3.13(m,4H)、3.07−2.91(m,4H)、2.85−2.71(m,4H)、2.07−1.90(m,2H)。13C NMR(126MHz,D2O)δ51.08、29.95、28.16、25.50。
3,3’−(プロパン−1,3−ジイルビス(スルファンジイル))ジプロピルスルホナート(化合物12):
3−ブロモプロピルスルホン酸ナトリウム塩(22.4g、100mmol)およびナトリウムメトキシド(5.40g、100mmol)のエタノール(350mL)中の溶液に、室温で、1,3−プロパンジチオール(5mL、50.0mmol)のEtOH(25.0mL)中の溶液が滴下添加された。この反応混合物は一晩還流加熱された。この反応混合物は室温まで冷却され、次いで2NのHClを用いてpH1〜2まで酸性化された。得られた懸濁物は75℃まで加熱され、そして透明な薄黄色溶液が得られるまで水が少しづつに分けてゆっくりと添加された。この溶液は室温に平衡化され、次いで5℃に冷却された。得られた白色沈殿は濾別され、冷EtOHで洗浄させられ、乾燥させられた。粗生成物はエタノールから再結晶化されて、白色固体として10.4gの化合物12(26.69mol、59.4%)を得た。1H NMR(500MHz,D2O)δ3.17−3.07(m,4H)、2.88−2.73(m,8H)、2.18−2.09(m,4H)、2.06−1.92(m,2H)。13C NMR(126MHz,D2O)δ49.88、29.78、28.55、24.26。
2,2’−[1,2−エタンジイルビス(チオ)]ビス−エタノール(比較例1):
2−クロロエタノール(48.1g、0.597mol)のアセトニトリル(50mL)中の溶液が、1,2−ジチオエタン(25.0g、0.265mol)および炭酸ナトリウム(70.3g、0.663mol)のアセトニトリル(100mL)の溶液にゆっくりと滴下添加された。この添加が完了した後で、この反応混合物は3時間にわたって還流加熱され、次いで周囲温度まで冷却された。固体を溶解させるためにDI水(100mL)が添加され、そして得られた溶液はEtOAc(200mL)で抽出された。有機相は水(100mL)およびブライン(50mL)で洗浄され、次いでNa2SO4で乾燥させられた。濃縮乾固し、次いでEtOAcから再結晶化させることによって、4.60g(9.5%)の比較例1を白色固体として得た。1H NMR(CDCl3)δ3.76(t,J=5.9Hz,4H)、2.78(s,4H)、2.77(t,J=5.9Hz,4H)。13C NMR(CDCl3)δ60.75、35.41、32.08。
2,2’−(メチレンビス(スルファンジイル))ジエタノール(比較例2):
凝縮器、攪拌棒および添加漏斗を備えた丸底フラスコに、2−メルカプトエタノール(6.00mL、85.4mmol)および粉砕された水酸化ナトリウム(3.41g、85.4mmol)が入れられた。このフラスコは氷浴中に配置され、そしてフラスコ内容物は攪拌させられた。反応混合物を20℃未満に維持しつつ、ジブロモメタン(2.93mL、42.7mmol)が添加漏斗によって滴下添加された。添加完了後に、この反応混合物は室温に平衡化され、次いで80℃で約2時間にわたって還流された。室温まで冷却した後で、この混合物は濃縮乾固され、次いで最小限の量の水に溶解させられ、濾過され、そして濃縮乾固された。得られた固体の酢酸エチルでの抽出、次いで濃縮乾固によって、無色の低融点固体として比較例2の化合物(7.05g、98%)を得た。1H NMR(500MHz,D2O)δ3.99(s,2H)、3.94(t,J=6.3Hz,4H),3.00(t,J=6.3Hz,4H)。13C NMR(126MHz,D2O)δ60.43、34.65、33.14。
化合物1〜12並びに比較例1および2の溶解度が以下のように評価された:25mgの各化合物がバイアルに秤量され、そして5mLの17%メタンスルホン酸(MSA)/DI水溶液が添加された。化合物が溶解した場合には、さらに25mg(増分で)づつ、それ以上溶解しなくなるまでまたはこの5mLに250mgが溶解するまで、その化合物が添加された。結果は表1に示される。
以下のスルフィド化合物を製造するために実施例1〜10の一般的な手順が繰り返される。
メタンスルホン酸スズからの75g/Lのスズ、メタンスルホン酸銀からの0.4g/Lの銀、275mL/Lの70%メタンスルホン酸、界面活性剤として4g/Lのエトキシ化ビスフェノールA(13エチレンオキシド単位)、1g/Lのエチルマルトール、50mg/Lのペンタヒドロキシフラボン、1g/Lのヒドロキノンモノスルホン酸カリウム塩、錯化剤としてのスルフィド化合物、およびDI水(残部)を一緒にすることによって、スズ−銀(Sn−Ag)電気めっき浴が調製された。表3は使用される錯化剤およびその量を示す。Sn−Ag浴13−Cは米国特許第6,998,036号および第7,628,903号からの従来の錯化剤を使用する。
NeXXめっきツールにおいて、上記Sn−Ag電気めっき浴のそれぞれを用いて、200mmのパターン形成されたシリコンウェハ上にSn−Agはんだバンプが電気めっきされた。このパターン形成されたウェハは75μm直径のバイアおよび3つの異なるピッチサイズ(150、225および375μm)、3〜20%のめっき可能面積、75μmのネガティブドライフィルムレジスト高さ、および1kÅ Ti/3kÅ Cuのシードを有していた。5μmの高さの銅スタッドがUBM層として使用され、Sn−Agはんだバンプとウェハとの間の接着を増強させた。このウェハは素早い振動を伴って垂直めっきされた。白金めっきチタンが不溶性アノードとして使用され、12〜20Å/dm2の電流密度が使用された。
によって、ダイ内(within−die;WID)均一性(または、共平面性(coplanarity))を得た。共平面性の値(すなわち、ダイ内均一性)が小さくなるほど、Sn−Agはんだバンプがより均一になる。はんだバンプの均一性はウェハへの部品の適切な取り付けを確実にするのに重要である。
以下の界面活性剤およびスルフィド化合物錯化剤が使用される以外は、実施例15の手順が繰り返される。界面活性剤Aは式
Claims (9)
- 浴可溶性銀イオン源、水、酸電解質、および式
Y1−(CR1R2)m−S−(CR3R4)x−S−(CR5R6)n−Y2 、
- 浴可溶性スズイオン源をさらに含む請求項1の組成物。
- 各R1、R2、R5およびR6 における前記(C 1 −C 6 )アルキルおよび前記ヒドロキシ置換(C 1 −C 6 )アルキルがそれぞれ(C1−C4)アルキルおよびヒドロキシ置換(C1−C4)アルキルに限定される請求項1の組成物。
- m=1〜4である請求項1の組成物。
- n=1〜4である請求項1の組成物。
- Y1とY2とが同じである請求項1の組成物。
- xは1、3、4、5または6であり、Y1およびY2が独立してCO2HおよびSO3Hから選択され;各R1、R2、R5およびR6が独立してHおよび(C1−C3)アルキルから選択され;各R3およびR4が独立してHおよび(C1−C3)アルキルから選択され;m=1〜4;n=1〜4;並びに、x=1〜4である請求項1の組成物。
- 請求項1の組成物を基体と接触させ:
一定期間にわたって電位を適用して、前記基体上に銀含有層を析出させる;
ことを含む、スズ−銀層を析出させる方法。
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US10428436B2 (en) * | 2016-07-18 | 2019-10-01 | Rohm And Haas Electronic Materials Llc | Indium electroplating compositions containing amine compounds and methods of electroplating indium |
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US20130256145A1 (en) | 2013-10-03 |
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