JP2011190260A - めっき浴および方法 - Google Patents
めっき浴および方法 Download PDFInfo
- Publication number
- JP2011190260A JP2011190260A JP2011055905A JP2011055905A JP2011190260A JP 2011190260 A JP2011190260 A JP 2011190260A JP 2011055905 A JP2011055905 A JP 2011055905A JP 2011055905 A JP2011055905 A JP 2011055905A JP 2011190260 A JP2011190260 A JP 2011190260A
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- JP
- Japan
- Prior art keywords
- copper
- alkyl
- aryl
- reaction product
- compounds
- 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.)
- Granted
Links
- 238000007747 plating Methods 0.000 title abstract description 58
- 238000000034 method Methods 0.000 title abstract description 23
- 229910052802 copper Inorganic materials 0.000 claims abstract description 98
- 239000010949 copper Substances 0.000 claims abstract description 98
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 91
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 44
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000000758 substrate Substances 0.000 claims abstract description 40
- 238000009713 electroplating Methods 0.000 claims abstract description 36
- 150000002118 epoxides Chemical class 0.000 claims abstract description 23
- 239000003792 electrolyte Substances 0.000 claims abstract description 15
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910001431 copper ion Inorganic materials 0.000 claims abstract description 12
- -1 imidazole compound Chemical class 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 238000009499 grossing Methods 0.000 claims description 24
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 15
- 229910052727 yttrium Inorganic materials 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 238000000151 deposition Methods 0.000 claims description 7
- 150000002460 imidazoles Chemical class 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
- 150000001923 cyclic compounds Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 19
- 239000002184 metal Substances 0.000 abstract description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 239000003112 inhibitor Substances 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000001879 copper Chemical class 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 230000024121 nodulation Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000001788 irregular Effects 0.000 description 4
- 0 *C1OC1C*CC1OC1N Chemical compound *C1OC1C*CC1OC1N 0.000 description 3
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910021645 metal ion Inorganic materials 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
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000126 substance Chemical group 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- IFPMZBBHBZQTOV-UHFFFAOYSA-N 1,3,5-trinitro-2-(2,4,6-trinitrophenyl)-4-[2,4,6-trinitro-3-(2,4,6-trinitrophenyl)phenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C=2C(=C(C=3C(=CC(=CC=3[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)C(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O IFPMZBBHBZQTOV-UHFFFAOYSA-N 0.000 description 2
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 2
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- BSXVKCJAIJZTAV-UHFFFAOYSA-L copper;methanesulfonate Chemical compound [Cu+2].CS([O-])(=O)=O.CS([O-])(=O)=O BSXVKCJAIJZTAV-UHFFFAOYSA-L 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000006259 organic additive 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000011179 visual inspection Methods 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 description 1
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- MHGUSQPDQPUNQD-UHFFFAOYSA-N 2-(2,2-disulfoethyldisulfanyl)ethane-1,1-disulfonic acid Chemical compound OS(=O)(=O)C(S(O)(=O)=O)CSSCC(S(O)(=O)=O)S(O)(=O)=O MHGUSQPDQPUNQD-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- YYAQQHMVACMQHH-UHFFFAOYSA-N 2-[[2-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1CCCCC1COCC1CO1 YYAQQHMVACMQHH-UHFFFAOYSA-N 0.000 description 1
- YXEXMVJHQLWNGG-UHFFFAOYSA-N 3-(3,3-disulfopropyldisulfanyl)propane-1,1-disulfonic acid Chemical compound OS(=O)(=O)C(S(O)(=O)=O)CCSSCCC(S(O)(=O)=O)S(O)(=O)=O YXEXMVJHQLWNGG-UHFFFAOYSA-N 0.000 description 1
- FULCXPQDMXUVSB-UHFFFAOYSA-N 3-(3-sulfanylpropylsulfonyloxy)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCOS(=O)(=O)CCCS FULCXPQDMXUVSB-UHFFFAOYSA-N 0.000 description 1
- WRBSVISDQAINGQ-UHFFFAOYSA-N 3-(dimethylcarbamothioylsulfanyl)propane-1-sulfonic acid Chemical compound CN(C)C(=S)SCCCS(O)(=O)=O WRBSVISDQAINGQ-UHFFFAOYSA-N 0.000 description 1
- REEBJQTUIJTGAL-UHFFFAOYSA-N 3-pyridin-1-ium-1-ylpropane-1-sulfonate Chemical compound [O-]S(=O)(=O)CCC[N+]1=CC=CC=C1 REEBJQTUIJTGAL-UHFFFAOYSA-N 0.000 description 1
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical compound [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZWFRZGJUJSOHGL-UHFFFAOYSA-N [Bi].[Cu].[Sn] Chemical compound [Bi].[Cu].[Sn] ZWFRZGJUJSOHGL-UHFFFAOYSA-N 0.000 description 1
- PQIJHIWFHSVPMH-UHFFFAOYSA-N [Cu].[Ag].[Sn] Chemical compound [Cu].[Ag].[Sn] PQIJHIWFHSVPMH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940108925 copper gluconate Drugs 0.000 description 1
- YCKOAAUKSGOOJH-UHFFFAOYSA-N copper silver Chemical compound [Cu].[Ag].[Ag] YCKOAAUKSGOOJH-UHFFFAOYSA-N 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
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- MRYMYQPDGZIGDM-UHFFFAOYSA-L copper;4-methylbenzenesulfonate Chemical compound [Cu+2].CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 MRYMYQPDGZIGDM-UHFFFAOYSA-L 0.000 description 1
- SSOVMNXYUYFJBU-UHFFFAOYSA-L copper;ethanesulfonate Chemical compound [Cu+2].CCS([O-])(=O)=O.CCS([O-])(=O)=O SSOVMNXYUYFJBU-UHFFFAOYSA-L 0.000 description 1
- MNEVGNCIZWZKLR-UHFFFAOYSA-N copper;phenol Chemical compound [Cu].OC1=CC=CC=C1.OC1=CC=CC=C1 MNEVGNCIZWZKLR-UHFFFAOYSA-N 0.000 description 1
- NPSDYIWFLLIHOT-UHFFFAOYSA-L copper;propane-1-sulfonate Chemical compound [Cu+2].CCCS([O-])(=O)=O.CCCS([O-])(=O)=O NPSDYIWFLLIHOT-UHFFFAOYSA-L 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 description 1
- ALKZAGKDWUSJED-UHFFFAOYSA-N dinuclear copper ion Chemical compound [Cu].[Cu] ALKZAGKDWUSJED-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000454 electroless metal deposition Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940044652 phenolsulfonate Drugs 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- SOUPVZCONBCBGI-UHFFFAOYSA-M potassium;3-sulfanylpropane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)CCCS SOUPVZCONBCBGI-UHFFFAOYSA-M 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- FRTIVUOKBXDGPD-UHFFFAOYSA-M sodium;3-sulfanylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCS FRTIVUOKBXDGPD-UHFFFAOYSA-M 0.000 description 1
- KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical class [Na+].CCS([O-])(=O)=O KQFAFFYKLIBKDE-UHFFFAOYSA-M 0.000 description 1
- NPAWNPCNZAPTKA-UHFFFAOYSA-M sodium;propane-1-sulfonate Chemical compound [Na+].CCCS([O-])(=O)=O NPAWNPCNZAPTKA-UHFFFAOYSA-M 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
Classifications
-
- 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
- C25D3/38—Electroplating: Baths therefor from solutions of copper
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electroplating And Plating Baths Therefor (AREA)
- Electroplating Methods And Accessories (AREA)
- Chemically Coating (AREA)
Abstract
【解決手段】特定のイミダゾール化合物と特定のエポキシド含有化合物との反応生成物である平滑化剤を含む、銅めっき浴である。金属電気めっき浴に使用される平滑化剤の量は、0.25〜5000ppm、である。該銅電気めっき浴中の銅と、めっきされる基体とを接触させ;並びに、基体上に銅層を堆積させるのに充分な時間にわたって電流密度を適用する:ことを含む、基体上に銅を堆積する。
【選択図】なし
Description
本発明は、銅イオン源、電解質および平滑化剤を含む銅電気めっき浴であって、平滑化剤が1種以上のイミダゾール化合物と1種以上のエポキシド含有化合物との反応生成物であって、少なくとも1種のイミダゾール化合物が式:
本発明は、銅イオン源、電解質および平滑化剤を含む銅電気めっき浴であって、平滑化剤が1種以上のイミダゾール化合物と1種以上のエポキシド含有化合物との反応生成物であって、少なくとも1種のイミダゾール化合物が式:
凝縮器および温度計を備えた250mLの三首丸底フラスコに、100mmolの2,4−ジメチルイミダゾールおよび12mLの脱イオン(DI)水が入れられ、次いで、63mmolの1,4−ブタンジオールジグリシジルエーテルを添加した。得られた混合物を、95℃に設定された油浴を用いて約5時間加熱し、次いで、さらに8時間室温で攪拌し続けた。アンバーレッド色の粘稠な反応生成物が200mL容量フラスコに移され、DI水ですすがれ、200mLの印まで調節された。この反応生成物(反応生成物1)溶液は、さらに精製することなく使用された。1H NMR(500MHz、CH3OH−d6)による反応生成物1の分析は、構造を確認する次のピークを示した:δppm:7.55−6.52(m,1H,Harom);4.35−3.26(m,10H,4CH2−O、2CH−OH、2CH2−N);2.35−2.09(m,6H,3CH3);および1.75−1.56(m,2.88H,2CH2)。
凝縮器、温度計を備えた250mLの三首丸底フラスコに、100mmolの2,4−ジメチルイミダゾールおよび10mLのDI水が入れられた。次いで、56.7mmolの1,4−ブタンジオールジグリシジルエーテルおよび6.3mmolの1,4−シクロヘキサンジメタノールジグリシジルエーテルをフラスコに添加し、次いで、追加の5mLのDI水を添加した。この溶液を95℃の油浴を用いて5時間加熱した。加熱後、反応混合物は攪拌しつつ一晩冷却させられた。次の日、アンバーレッド色の粘稠な反応生成物が水溶液として得られた。この反応生成物(反応生成物2)溶液は、さらに精製することなく使用された。
1,4−ブタンジオールジグリシジルエーテル(63mmol)、25mmolのイミダゾールおよび75mmolの4−フェニルイミダゾールが室温で、丸底反応フラスコに入れられた。次いで、30mLのDI水がこのフラスコに添加された。最初に形成された白色懸濁物は、反応温度が上昇するにつれて徐々に消失し、相分離した混合物になった。この反応混合物は、98℃に設定された油浴を用いて2時間加熱された。2mLの濃硫酸を反応フラスコに添加した後で、溶液は淡黄色で透明になった。この混合物をさらに3時間加熱し、さらに8時間室温で攪拌し続けた。得られた琥珀色の反応生成物は容量フラスコに移され、0.5〜1%の硫酸ですすがれ、希釈された。この反応生成物(反応生成物3)溶液は、さらに精製することなく使用された。1H NMR(500MHz、DMSO−d6)による反応生成物3の分析は、構造を確認する次のピークを示した:δppm:9.22−7.22(m,24H,Harom);4.52−3.00(m,37.2H(2.65×14H),4CH2−O、2CH−OH、2CH2−N);および1.74−1.24(m,10.6H(2.653×4H),2CH2)。
実施例1、2または3の一般的手順を用いて、表1の反応生成物が製造された。反応生成物のUV−吸収は、アジレント(Agilent)8453分光光度計を用いて水中で測定され、そしてλmax(nm)は以下の表に報告される。
銅めっき浴は、75g/L銅(硫酸銅五水和物として)、240g/Lの硫酸、50ppmのクロリドイオン、0.5ppmの促進剤および1.5g/Lの抑制剤を一緒にすることにより製造された。促進剤は、スルホン酸基および1000未満の分子量を有するジスルフィド化合物であった。抑制剤は、5,000未満の分子量および末端ヒドロキシル基を有するEO/POコポリマーであった。めっき浴は、実施例1からの反応生成物10mL/Lも含んでいた。
実施例2〜4の反応生成物のそれぞれが使用されたことを除いて、概して実施例5に従って様々な銅めっき浴が製造された。
スルーホールを有する両面FR4 PCB(5×9.5cm)のサンプル(厚み3.2mmまたは1.6mmのいずれか)が、実施例6に従った銅めっき浴を使用するハーリングセル内でめっきされた。3.2mm厚のサンプルは直径0.3mmのスルーホールを有しており、1.6mm厚のサンプルは直径0.25mmのスルーホールを有していた。それぞれの浴の温度は25℃であった。2.16A/dm2(20A/ft2)の電流密度が3.2mmのサンプルに適用され、3.24A/dm2(30A/ft2)の電流密度が1.6mmのサンプルに適用され、それぞれの場合において、めっきは80分間にわたって行われた。銅めっきされたサンプルは分析されて、以下の方法に従って、めっき浴の均一電着性(TP)、ノジュール形成、およびクラッキングパーセントを決定した。各反応生成物(平滑化剤)および促進剤(ACC.)の量、並びにめっきデータが表3に示される。
実施例1〜3の手順に概して従って、表4の比較反応生成物が製造された。
平滑化剤として表5に示される量の実施例1、4または8からの反応生成物を含む銅めっき浴が製造された。銅めっき浴は硫酸銅五水和物として75g/Lの銅、240g/Lの硫酸、60ppmのクロリドイオン、0.5〜3ppmの促進剤(ACC)および1.5g/Lの抑制剤も含んでいた。促進剤の具体的な量は表5に報告される。比較反応生成物C−2およびC−4を含む銅めっき浴は、60ppmの代わりに50ppmのクロリドイオンを含んでいた。促進剤は、スルホン酸基を有し、1000未満の分子量を有するジスルフィド化合物であった。抑制剤は、5,000未満の分子量および末端ブチル基を有するEO/POコポリマーであった。
それぞれが60ppmのクロリドイオンおよび1ppmの促進剤を含んでいたことを除いて、実施例5の手順に従って、2種類の銅めっき浴が製造された。平滑化剤として、浴10−1は1ppmの反応生成物38を含んでおり、浴10−2は5ppmの反応生成物38を含んでいた。
Claims (10)
- R1、R2およびR3が、独立して、H、(C1−C8)アルキル、(C2−C7)アルケニルもしくはアリールから選択される、請求項1に記載の反応生成物。
- (C1−C12)アルキル基および(C2−C12)アルケニル基が、それぞれ、ヒドロキシル基、ハロゲンおよびアリール基の1種以上で置換されている、請求項1に記載の反応生成物。
- エポキシド含有化合物が下記式:
の化合物から選択される、請求項1に記載の反応生成物。 - R1およびR2の少なくとも一方が、(C1−C8)アルキル、(C3−C7)アルケニルおよびアリールから選択される、請求項5に記載の銅電気めっき浴。
- R3がHである、請求項6に記載の銅電気めっき浴。
- エポキシド含有化合物が1〜3個のエポキシ基を含む、請求項5に記載の銅電気めっき浴。
- エポキシド含有化合物が下記式:
の化合物から選択される、請求項5に記載の銅電気めっき浴。 - 請求項5の銅電気めっき浴中の銅と、めっきされる基体とを接触させ;並びに、
基体上に銅層を堆積させるのに充分な時間にわたって電流密度を適用する:
ことを含む、基体上に銅を堆積する方法。
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Cited By (4)
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JP2011207878A (ja) * | 2010-03-15 | 2011-10-20 | Rohm & Haas Electronic Materials Llc | めっき浴および方法 |
JP2019023352A (ja) * | 2016-02-15 | 2019-02-14 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | スルーホールを充填してボイド及び他の欠陥を低減する方法 |
JP2017222925A (ja) * | 2016-03-29 | 2017-12-21 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC | メガサイズのフォトレジスト画定フィーチャを電気めっきすることが可能な電気銅めっき浴及び電気めっき方法 |
KR20230142785A (ko) | 2021-02-15 | 2023-10-11 | 가부시키가이샤 아데카 | 전해 도금액용 첨가제, 전해 도금액, 전해 도금 방법 및 금속층의 제조 방법 |
Also Published As
Publication number | Publication date |
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EP2366692B1 (en) | 2013-02-20 |
US8268158B2 (en) | 2012-09-18 |
US20110220512A1 (en) | 2011-09-15 |
JP6054594B2 (ja) | 2016-12-27 |
TWI428326B (zh) | 2014-03-01 |
KR101739410B1 (ko) | 2017-05-24 |
CN102250319A (zh) | 2011-11-23 |
TW201139382A (en) | 2011-11-16 |
KR20110103891A (ko) | 2011-09-21 |
US20110290660A1 (en) | 2011-12-01 |
CN102888629B (zh) | 2014-12-31 |
CN102888629A (zh) | 2013-01-23 |
EP2366692A3 (en) | 2011-11-02 |
EP2366692A2 (en) | 2011-09-21 |
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