JP2017036499A - ピリジルアルキルアミンとビスエポキシドとの反応生成物を含有する電気銅めっき浴からフォトレジスト画定フィーチャを電気めっきする方法 - Google Patents
ピリジルアルキルアミンとビスエポキシドとの反応生成物を含有する電気銅めっき浴からフォトレジスト画定フィーチャを電気めっきする方法 Download PDFInfo
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- JP2017036499A JP2017036499A JP2016149326A JP2016149326A JP2017036499A JP 2017036499 A JP2017036499 A JP 2017036499A JP 2016149326 A JP2016149326 A JP 2016149326A JP 2016149326 A JP2016149326 A JP 2016149326A JP 2017036499 A JP2017036499 A JP 2017036499A
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- Prior art keywords
- copper
- photoresist
- pillars
- reaction product
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- 229910052802 copper Inorganic materials 0.000 title claims abstract description 143
- 239000010949 copper Substances 0.000 title claims abstract description 143
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 134
- 238000007747 plating Methods 0.000 title claims abstract description 82
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 59
- 239000007795 chemical reaction product Substances 0.000 title claims abstract description 52
- 238000009713 electroplating Methods 0.000 title claims abstract description 37
- 150000001412 amines Chemical class 0.000 title abstract 2
- 239000000758 substrate Substances 0.000 claims abstract description 42
- 239000003112 inhibitor Substances 0.000 claims abstract description 14
- 239000003792 electrolyte Substances 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000006657 (C1-C10) hydrocarbyl group Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 229910000679 solder Inorganic materials 0.000 description 31
- 239000000203 mixture Substances 0.000 description 23
- -1 and R 2 —R 5 is Chemical compound 0.000 description 22
- 230000008569 process Effects 0.000 description 22
- 235000012431 wafers Nutrition 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 239000010703 silicon Substances 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 8
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 8
- 229910001431 copper ion Inorganic materials 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical compound C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- WIYCQLLGDNXIBA-UHFFFAOYSA-L disodium;3-(3-sulfonatopropyldisulfanyl)propane-1-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)CCCSSCCCS([O-])(=O)=O WIYCQLLGDNXIBA-UHFFFAOYSA-L 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000011800 void material Substances 0.000 description 3
- 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 2
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 2
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 2
- JROOCDXTPKCUIO-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)CCOCC1CO1 JROOCDXTPKCUIO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- COCFIBRMFPWUDW-UHFFFAOYSA-N 2-methylquinolin-4-amine Chemical compound C1=CC=CC2=NC(C)=CC(N)=C21 COCFIBRMFPWUDW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000012935 Averaging Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 229910001128 Sn alloy Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- UUQMNUMQCIQDMZ-UHFFFAOYSA-N betahistine Chemical compound CNCCC1=CC=CC=N1 UUQMNUMQCIQDMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 230000008021 deposition Effects 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- WYHXNQXDQQMTQI-UHFFFAOYSA-N n-benzylpyridin-2-amine Chemical compound C=1C=CC=CC=1CNC1=CC=CC=N1 WYHXNQXDQQMTQI-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000006259 organic additive Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000012536 packaging technology Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product 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
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000006526 (C1-C2) 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
- 0 *c1c(*)c(*)nc(*)c1* Chemical compound *c1c(*)c(*)nc(*)c1* 0.000 description 1
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-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
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 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
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910000978 Pb alloy Inorganic materials 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
- FOYFLYXUNINKFM-UHFFFAOYSA-N SCCC(CC)S(=O)(=O)C(CCS)CC Chemical compound SCCC(CC)S(=O)(=O)C(CCS)CC FOYFLYXUNINKFM-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229940108925 copper gluconate Drugs 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- YRNNKGFMTBWUGL-UHFFFAOYSA-L copper(ii) perchlorate Chemical compound [Cu+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O YRNNKGFMTBWUGL-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
- RIOSFUBRIQHOMS-UHFFFAOYSA-L copper;benzenesulfonate Chemical compound [Cu+2].[O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C1=CC=CC=C1 RIOSFUBRIQHOMS-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
- BSXVKCJAIJZTAV-UHFFFAOYSA-L copper;methanesulfonate Chemical compound [Cu+2].CS([O-])(=O)=O.CS([O-])(=O)=O BSXVKCJAIJZTAV-UHFFFAOYSA-L 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
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000000847 optical profilometry Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000642 polymer Polymers 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
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 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
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical compound [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
- 238000003860 storage Methods 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 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
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Abstract
【解決手段】ピリジルアルキルアミンとビスエポキシドとの反応生成物、電解質、促進剤、及び抑制剤を含む電気銅めっき浴を用いて、開口部を有するフォトレジストの層を有する基板に銅/フォトレジスト画定フィーチャをめっきする方法。
【選択図】図1
Description
%TIR=[高さcenter−高さedge]/高さmax×100
式中、高さcenterは、その中心軸に沿って測定されるピラーの高さであり、高さedgeは、エッジ上の最も高い点でそのエッジに沿って測定されるピラーの高さである。高さmaxは、ピラーの底部からその上部の最も高い点までの高さである。高さmaxは、正規化因子である。
TIR=高さcenter−高さedge
式中、高さcenter及び高さedgeは、上で定義した通りである。
%WID=1/2×[(高さmax−高さmin)/高さavg]×100
式中、高さmaxは、ピラーの最も高い部分で測定される、基板上に電気めっきされたピラーのアレイの最も高いピラーの高さである。高さminは、ピラーの最も高い部分で測定される、基板上に電気めっきされたピラーのアレイの最も短いピラーの高さである。高さavgは、基板上に電気めっきされた全てのピラーの平均高さである。
凝縮器および温度計を装備した125mL三口丸底フラスコに、100mmolの2−(2−アミノエチル)ピリジンおよび20mLの脱イオン水を加えた。混合物を80℃まで加熱した後、100mmolの1,4−ブタンジオールジグリシジルエーテルを滴下で加えた。得られた混合物を、90℃に設定した油浴を用いて約4時間加熱し、次いで、さらに4時間室温で撹拌した。反応生成物(反応生成物1)溶液を、さらに精製することなく使用した。
凝縮器および温度計を装備した125mL三口丸底フラスコに、100mmolの2−(2−メチルアミノエチル)ピリジン及び20mLの脱イオン水を加えた。混合物を80℃まで加熱した後、100mmolの1,4−ブタンジオールジグリシジルエーテルを滴下で加えた。得られた混合物を、90℃に設定した油浴を用いて約4時間加熱し、次いで、さらに4時間室温で撹拌した。反応生成物を水で希釈し、保存容器に移し、さらに精製することなく使用した。
凝縮器および温度計を装備した125mL三口丸底フラスコ内で、90mmolの2−ベンジルアミノピリジン、10mmolの2−(2−アミノエチル)ピリジンを、20mLの脱イオン水及び6mlの50%硫酸の混合物に加えた。得られた混合物を80℃まで加熱した後、100mmolの1,4−ブタンジオールジグリシジルエーテルを滴下で加えた。反応混合物を、90℃に設定した油浴を用いて約4時間加熱し、次いで、さらに4時間室温で撹拌した。反応生成物(反応生成物3)溶液を、さらに精製することなく使用した。
凝縮器および温度計を装備した125mL三口丸底フラスコに、100mmolの2−(2−アミノエチル)ピリジン及び20mLの脱イオン水を加えた。混合物を70℃まで加熱した後、80mmolの1,2,7,8−ジエポキシオクタンを滴下で加えた。得られた混合物を、80℃に設定した油浴を用いて約4時間加熱し、次いで、さらに4時間室温で撹拌した。酸性水を用いて反応生成物(反応生成物4)を希釈し、さらに精製することなく使用した。
硫酸銅五水和物からの40g/L銅イオン、140g/L硫酸、50ppm塩化物イオン、5ppmの促進剤、及び2g/Lの抑制剤を組み合わせることによって、水性酸電気銅めっき浴を調製した。促進剤は、ビス(ナトリウム−スルホプロピル)ジスルフィドであった。抑制剤は、約1,000の重量平均分子量及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。電気めっき浴はまた、実施例1からの1ppmの反応生成物1も含有していた。浴のpHは、1未満であった。
%TIR=[高さcenter−高さedge]/高さmax×100、
TIR=高さcenter−高さedge
%WID=1/2×[(高さmax−高さmin)/高さavg]×100
厚さ50μmのパターン化されたフォトレジスト及び複数の開口部を有するシリコンウエハセグメント(IMAT,Inc.、Vancouver,WAから入手可能)を、実施例5の電気銅めっき浴に浸漬した。陽極は、可溶性銅電極であった。ウエハ及び陽極を整流器に接続し、開口部の底部の露出されたシード層上に銅ピラーを電気めっきした。めっき中の電流密度は9ASDであり、電気銅めっき浴の温度は室温であった。
シリコンウエハが厚さ40μmのパターン化されたフォトレジスト及び直径20μmの複数の開口部を有していたこと(IMAT,Inc.、Vancouver,WAから入手可能)を除いて、実施例5に記載した銅ピラーめっきプロセスを繰り返した。反応生成物1は、10ppmの量で電気銅めっき浴に含まれ、めっきは4.5ASDで行われた。8つの銅ピラーをそれらの形態について分析した。
反応生成物1が10ppmの量で電気銅めっき浴に含まれたことを除いて、実施例5に記載した銅ピラーめっきプロセスを繰り返した。8つのピラーをそれらの形態について分析した。
反応生成物1が0.25ppmの量で電気銅めっき浴に含まれ、電気銅めっき浴が30℃の温度であり、銅めっきが14ASDの電流密度で行われたことを除いて、実施例5に記載した銅ピラーめっきプロセスを繰り返した。下の表4は、300mmシリコンウエハセグメントの分析から得られたデータを開示している。
シリコンウエハが厚さ40μmのパターン化されたフォトレジスト及び直径20μmの複数の開口部を有していたこと(IMAT,Inc.、Vancouver,WAから入手可能)を除いて、実施例5に記載した銅ピラーめっきプロセスを繰り返した。反応生成物2は、1ppmの量で電気銅めっき浴に含まれ、めっきは4.5ASDで行われた。8つの銅ピラーをそれらの形態について分析した。
シリコンウエハが厚さ50μmのパターン化されたフォトレジスト及び直径50μmの複数の開口部を有しており(IMAT,Inc.、Vancouver,WAから入手可能)、反応生成物1の代わりに反応生成物3が浴に含まれたことを除いて、実施例5に記載した銅ピラーめっきプロセスを繰り返した。反応生成物3は、10ppmの量で電気銅めっき浴に含まれ、めっきは9ASDで行われた。8つの銅ピラーをそれらの形態について分析した。
電気銅めっき浴中の反応生成物が上記実施例3の反応生成物3であったことを除いて、実施例6の方法を繰り返した。銅ピラーの上部をSOLDERON(商標)BP TS6000錫/銀電気めっき液でめっきし、次いで、実施例6に記載されるようにリフローさせた。リフロー後、FIB−SEMを使用して8つの銅ピラーを横断面で切断し、銅ピラーとはんだとの界面をボイドについて調べた。はんだと銅ピラーとの界面にボイドは観察されなかった。
反応生成物1の代わりに反応生成物4が浴に含まれたこと、及び銅めっきが14ASDで行われたことを除いて、実施例5に記載した銅ピラーめっきプロセスを繰り返した。反応生成物4を1ppmの量で銅浴に加えた。8つのピラーをそれらの形態について分析した。
電気銅めっき浴中の反応生成物が上記実施例4の反応生成物4であったこと、及び電気銅めっきが14ASDで行われたことを除いて、実施例6の方法を繰り返した。銅ピラーの上部をSOLDERON(商標)BP TS6000錫/銀電気めっき液でめっきし、次いで、実施例6に記載されるようにリフローさせた。リフロー後、FIB−SEMを使用して8つの銅ピラーを横断面で切断し、銅ピラーとはんだとの界面をボイドについて調べた。はんだと銅ピラーとの界面にボイドは観察されなかった。
シリコンウエハが厚さ40μmのパターン化されたフォトレジスト及び直径20μmの複数の開口部を有していたこと(IMAT,Inc.、Vancouver,WAから入手可能)、ならびに反応生成物が銅浴に含まれなかったことを除いて、実施例5に記載した銅ピラーめっきプロセスを繰り返した。電気銅めっき浴は、次の構成成分を有していた:硫酸銅五水和物からの40g/L銅イオン、140g/L硫酸、50ppm塩化物イオン、5ppmのビス(ナトリウム−スルホプロピル)ジスルフィド,及び約1,000の重量平均分子量及び末端ヒドロキシル基を有する2g/LのEO/POコポリマー抑制剤。浴のpHは、1未満であった。水を除いて、さらなる構成成分は浴中に含まれなかった。電気銅めっきは9ASDで行われた。8つの銅ピラーをそれらの形態について分析した。
凝縮器および温度計を装備した125mL三口丸底フラスコ内で、90mmolの2−メチルキノリン−4−アミン、10mmolの2−(2−アミノエチル)ピリジンを、20mLの脱イオン水及び5mlの50%硫酸の混合物に加えた。混合物を80℃まで加熱した後、100mmolの1,4−ブタンジオールジグリシジルエーテルを滴下で加えた。得られた混合物を、95℃に設定した油浴を用いて約4時間加熱し、次いで、さらに8時間室温で撹拌した。酸性水を用いて反応生成物(反応生成物5−比較例)を希釈し、さらに精製することなく使用した。
凝縮器および温度計を装備した125mL三口丸底フラスコに、50mmolの2−(2−アミノエチル)ピリジン及び20mLの脱イオン水を加えた。混合物を70℃まで加熱した後、50mmolのエピクロロヒドリンを滴下で加えた。得られた混合物を、80℃に設定した油浴を用いて約4時間加熱し、次いで、さらに4時間室温で撹拌した。反応生成物(反応生成物6−比較例)を水で希釈し、さらに精製することなく使用した。
反応生成物1の代わりに実施例16の反応生成物5−比較例が浴に含まれたことを除いて、実施例5に記載した銅ピラーめっきプロセスを繰り返した。電気銅めっきは9ASDで行われた。反応生成物5−比較例を、1ppmの量で銅浴に加えた。8つのピラーをそれらの形態について分析した。
反応生成物1の代わりに反応生成物5−比較例が10ppmの量で銅浴に加えられたことを除いて、実施例5の方法を繰り返した。結果は、実施例18と実質的に同じであり、ピラーの大半が粗い表面を有し、全てが皿状または陥没した上部を有していた。形状測定器は、ピラーを正確に読み取ることはできなかった。
反応生成物1の代わりに実施例17の反応生成物6−比較例が浴に含まれたことを除いて、実施例5に記載した銅ピラーめっきプロセスを繰り返した。電気銅めっきは、14ASDで行われた。反応生成物6−比較例を10ppmの量で銅浴に加えた。8つのピラーをそれらの形態について分析した。
Claims (9)
- フォトレジスト画定フィーチャを電気めっきするための方法であって、
a)フォトレジストの層を備える基板を提供することであって、前記フォトレジストの層は複数の開口部を備える、提供することと、
b)1つ以上のピリジルアルキルアミンと1つ以上のビスエポキシドとの1つ以上の反応生成物、電解質、1つ以上の促進剤、及び1つ以上の抑制剤を含む電気銅めっき浴を提供することと、
c)前記複数の開口部を有する前記フォトレジストの層を備える前記基板を前記電気銅めっき浴に浸漬することと、
d)複数の銅/フォトレジスト画定フィーチャを前記複数の開口部に電気めっきすることと、を含み、前記複数のフォトレジスト画定フィーチャは、−5%〜+12%の平均%TIRを含む、方法。 - 前記複数のフォトレジスト画定フィーチャの%WIDは、5%〜14%である、請求項1に記載の方法。
- 前記1つ以上の反応生成物は、前記電気銅めっき浴中に0.25ppm〜20ppmの量で存在する、請求項1に記載の方法。
- 前記1つ以上のフォトレジスト画定フィーチャは、ピラー、ボンドパッド、及び線幅/線間フィーチャから選択される、請求項1に記載の方法。
- 電流密度は、0.25ASD〜40ASDである、請求項1に記載の方法。
- −5%〜+12%の平均%TIR及び5%〜14%の%WIDを有する、基板上のフォトレジスト画定フィーチャのアレイ。
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |