JP6062425B2 - シリコン貫通ビアおよび相互接続フィーチャーのボトムアップ充填のための添加剤を含む金属電気めっきのための組成物 - Google Patents
シリコン貫通ビアおよび相互接続フィーチャーのボトムアップ充填のための添加剤を含む金属電気めっきのための組成物 Download PDFInfo
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- JP6062425B2 JP6062425B2 JP2014513298A JP2014513298A JP6062425B2 JP 6062425 B2 JP6062425 B2 JP 6062425B2 JP 2014513298 A JP2014513298 A JP 2014513298A JP 2014513298 A JP2014513298 A JP 2014513298A JP 6062425 B2 JP6062425 B2 JP 6062425B2
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- Prior art keywords
- polyaminoamide
- acid
- aryl
- alkyl
- copper
- 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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- 229910052751 metal Inorganic materials 0.000 title claims description 46
- 239000002184 metal Substances 0.000 title claims description 46
- 239000000203 mixture Substances 0.000 title claims description 41
- 238000011049 filling Methods 0.000 title claims description 11
- 229910052710 silicon Inorganic materials 0.000 title claims description 5
- 239000010703 silicon Substances 0.000 title claims description 5
- 238000009713 electroplating Methods 0.000 title description 37
- 239000000654 additive Substances 0.000 title description 22
- 239000010949 copper Substances 0.000 claims description 87
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 81
- 229910052802 copper Inorganic materials 0.000 claims description 81
- 125000003118 aryl group Chemical group 0.000 claims description 79
- 239000000758 substrate Substances 0.000 claims description 65
- 238000007747 plating Methods 0.000 claims description 56
- -1 ether amines Chemical class 0.000 claims description 55
- 239000003112 inhibitor Substances 0.000 claims description 51
- 238000000151 deposition Methods 0.000 claims description 30
- 230000008021 deposition Effects 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 239000001361 adipic acid Substances 0.000 claims description 10
- 235000011037 adipic acid Nutrition 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000007306 functionalization reaction Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229920001281 polyalkylene Polymers 0.000 claims description 7
- 229920000768 polyamine Polymers 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 6
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- SCHTXWZFMCQMBH-UHFFFAOYSA-N pentane-1,3,5-triamine Chemical compound NCCC(N)CCN SCHTXWZFMCQMBH-UHFFFAOYSA-N 0.000 claims description 4
- 230000005588 protonation Effects 0.000 claims description 4
- 238000005956 quaternization reaction Methods 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- HUDBNIFYBNWRJE-UHFFFAOYSA-N 3-n-(2-aminoethyl)propane-1,1,3-triamine Chemical compound NCCNCCC(N)N HUDBNIFYBNWRJE-UHFFFAOYSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004220 glutamic acid Substances 0.000 claims description 2
- 235000013922 glutamic acid Nutrition 0.000 claims description 2
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims 2
- 229910001431 copper ion Inorganic materials 0.000 claims 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- 229920002873 Polyethylenimine Polymers 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 229920001577 copolymer Polymers 0.000 description 19
- 235000012431 wafers Nutrition 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 16
- 125000002947 alkylene group Chemical group 0.000 description 13
- 229910021645 metal ion Inorganic materials 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 11
- 229940073608 benzyl chloride Drugs 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 230000000996 additive effect Effects 0.000 description 10
- 239000002168 alkylating agent Substances 0.000 description 10
- 229940100198 alkylating agent Drugs 0.000 description 10
- 239000004065 semiconductor Substances 0.000 description 10
- 229960000250 adipic acid Drugs 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 150000005846 sugar alcohols Polymers 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229910000365 copper sulfate Inorganic materials 0.000 description 8
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical group [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 8
- 239000003792 electrolyte Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 8
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 238000000399 optical microscopy Methods 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 125000001302 tertiary amino group Chemical group 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- 0 CC(C)(*)CCN(*)*N(*)CCC(N*NC(C(C)(C)*)=O)=O Chemical compound CC(C)(*)CCN(*)*N(*)CCC(N*NC(C(C)(C)*)=O)=O 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 238000009499 grossing Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 150000003951 lactams Chemical class 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 238000000137 annealing Methods 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
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- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 150000002772 monosaccharides Chemical class 0.000 description 3
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 3
- BXYVQNNEFZOBOZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound CN(C)CCCNCCCN(C)C BXYVQNNEFZOBOZ-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920000962 poly(amidoamine) Polymers 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920002717 polyvinylpyridine Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- CSPHGSFZFWKVDL-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CCl CSPHGSFZFWKVDL-UHFFFAOYSA-M 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 2
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 2
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 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
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000005700 Putrescine Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
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- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- WHDUKLPCKZTPFY-UHFFFAOYSA-N n,n'-diethylbutane-1,4-diamine Chemical compound CCNCCCCNCC WHDUKLPCKZTPFY-UHFFFAOYSA-N 0.000 description 1
- BEPGHZIEOVULBU-UHFFFAOYSA-N n,n'-diethylpropane-1,3-diamine Chemical compound CCNCCCNCC BEPGHZIEOVULBU-UHFFFAOYSA-N 0.000 description 1
- CZPRYVBLOUZRGD-UHFFFAOYSA-N n,n'-dimethylbutane-1,4-diamine Chemical compound CNCCCCNC CZPRYVBLOUZRGD-UHFFFAOYSA-N 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical group CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- UQUPIHHYKUEXQD-UHFFFAOYSA-N n,n′-dimethyl-1,3-propanediamine Chemical compound CNCCCNC UQUPIHHYKUEXQD-UHFFFAOYSA-N 0.000 description 1
- AYGYHGXUJBFUJU-UHFFFAOYSA-N n-[2-(prop-2-enoylamino)ethyl]prop-2-enamide Chemical compound C=CC(=O)NCCNC(=O)C=C AYGYHGXUJBFUJU-UHFFFAOYSA-N 0.000 description 1
- YQCFXPARMSSRRK-UHFFFAOYSA-N n-[6-(prop-2-enoylamino)hexyl]prop-2-enamide Chemical compound C=CC(=O)NCCCCCCNC(=O)C=C YQCFXPARMSSRRK-UHFFFAOYSA-N 0.000 description 1
- NJLPWLHBSPZUAS-UHFFFAOYSA-N n-[8-(prop-2-enoylamino)octyl]prop-2-enamide Chemical compound C=CC(=O)NCCCCCCCCNC(=O)C=C NJLPWLHBSPZUAS-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- TWHMVKPVFOOAMY-UHFFFAOYSA-N octanedioic acid Chemical compound OC(=O)CCCCCCC(O)=O.OC(=O)CCCCCCC(O)=O TWHMVKPVFOOAMY-UHFFFAOYSA-N 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NIFHFRBCEUSGEE-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O NIFHFRBCEUSGEE-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- YKEKYBOBVREARV-UHFFFAOYSA-N pentanedioic acid Chemical compound OC(=O)CCCC(O)=O.OC(=O)CCCC(O)=O YKEKYBOBVREARV-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 108010094020 polyglycine Proteins 0.000 description 1
- 229920000232 polyglycine polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- HJSRRUNWOFLQRG-UHFFFAOYSA-N propanedioic acid Chemical compound OC(=O)CC(O)=O.OC(=O)CC(O)=O HJSRRUNWOFLQRG-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- VRKNGZAPJYUNSN-UHFFFAOYSA-M sodium;3-(1,3-benzothiazol-2-ylsulfanyl)propane-1-sulfonate Chemical compound [Na+].C1=CC=C2SC(SCCCS(=O)(=O)[O-])=NC2=C1 VRKNGZAPJYUNSN-UHFFFAOYSA-M 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
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 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
- 239000013638 trimer Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/028—Polyamidoamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- 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
- C23C18/31—Coating with metals
- C23C18/38—Coating with copper
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D7/00—Electroplating characterised by the article coated
- C25D7/12—Semiconductors
- C25D7/123—Semiconductors first coated with a seed layer or a conductive layer
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
- C08K2003/3045—Sulfates
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/28—Manufacture of electrodes on semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/268
- H01L21/283—Deposition of conductive or insulating materials for electrodes conducting electric current
- H01L21/288—Deposition of conductive or insulating materials for electrodes conducting electric current from a liquid, e.g. electrolytic deposition
- H01L21/2885—Deposition of conductive or insulating materials for electrodes conducting electric current from a liquid, e.g. electrolytic deposition using an external electrical current, i.e. electro-deposition
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/70—Manufacture or treatment of devices consisting of a plurality of solid state components formed in or on a common substrate or of parts thereof; Manufacture of integrated circuit devices or of parts thereof
- H01L21/71—Manufacture of specific parts of devices defined in group H01L21/70
- H01L21/768—Applying interconnections to be used for carrying current between separate components within a device comprising conductors and dielectrics
- H01L21/76898—Applying interconnections to be used for carrying current between separate components within a device comprising conductors and dielectrics formed through a semiconductor substrate
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Metallurgy (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Electroplating And Plating Baths Therefor (AREA)
- Polyamides (AREA)
- Electroplating Methods And Accessories (AREA)
- Electrodes Of Semiconductors (AREA)
Description
a)本明細書に記載の金属電気めっき組成物を含む金属めっき浴を半導体基板と接触させるステップ、および
b)基板上に金属層を堆積させるのに十分な時間の間、ある電流密度を基板に加えるステップ。
[A]p[B]q[D]r (I)
またはその誘導体を含む
(式中、
Aは、
Bは、化学結合または
Dは、化学結合または
D1は、各繰返し単位1〜pに対して、独立して、化学結合または飽和、不飽和もしくは芳香族のC1〜C20有機基から選択される二価の基から選択され、
D2、D3は、独立して、直鎖または分枝のC1〜C10アルカンジイル(NおよびOから選択されるヘテロ原子で場合によって置換されていてもよい)から選択され、
D4は、直鎖または分枝のC2〜C6アルカンジイル、C6〜C10のアリールもしくはヘテロアリールジラジカル、C8〜C20アリールアルカンジイル、C8〜C20ヘテロアリールアルカンジイルから選択され、
D5は、直鎖または分枝のC1−〜C7−アルカンジイル(ヘテロ原子で場合によって置換されていてもよい)から選択され、
R1は、各繰返し単位1〜nに対して、独立して、H、C1〜C20−アルキルおよびC5〜C20−アリールまたはC5〜C20−ヘテロアリール(ヒドロキシル、アルコキシまたはアルコキシカルボニルで場合によって置換されていてもよい)から選択され、
nは2〜250の整数であり、
pは2〜150の整数であり、
qは0〜150の整数であり、
rは0〜150の整数であり、
D1、D4またはR1のうちの少なくとも1つが、C5〜C20芳香族部分を含むか、またはポリアミノアミドが、C5〜C20芳香族部分で官能化および/または四級化されている)。
E1、E2は、独立して、以下から選択され
(a)求核的に置換可能な脱離基、
(b)NH−(C1〜C20−アルキル)またはNH−(C1〜C20−アルケニル)またはNH−アリール、
(c)H−{NH−[D2−NR1]n−D3−NH}
(d)(C1〜C20−アルキル)−CO−{NH−[D2−NR2]n−D3−NH}、および
(e)(C1〜C20−アルケニル)−CO−{NH−[D2−NR2]n−D3−NH}、
(f)(C1〜C20−アリール)−CO−{NH−[D2−NR2]n−D3−NH}、
D1またはR1のうちの少なくとも1つは、C5〜C20芳香族部分を含む)。
D6は、各繰返し単位1〜sに対して、独立して、飽和、不飽和または芳香族のC1〜C20有機基から選択される二価の基であり、
D7は、直鎖または分枝のC2〜C6アルカンジイル、C6〜C10アリールジラジカル、C8〜C20アリールアルカンジイルから選択され、
R2は、各繰返し単位1〜sに対して、独立して、H、C1〜C20アルキル、C1〜C20アルケニル(ヒドロキシル、アルコキシまたはアルコキシカルボニルで場合によって置換されていてもよい)、またはアリールから選択され、2つのR2は、一緒になって環系を形成してもよく、
sは1〜250の整数であり、
D6、D7またはR2のうちの少なくとも1つが、C5〜C20芳香族部分を含むか、またはポリアミノアミドが、C5〜C20芳香族部分で官能化および/または四級化されている)。
E3、E4は、独立して、以下から選択され
(a)NH−C1〜C20−アルキルもしくはNH−C1〜C20−アルケニルもしくはNH−アリール、
(b)N−(C1〜C20−アルキル)2もしくはN−(C1〜C20−アルケニル)2もしくはN−(アリール)2もしくはN−(C1〜C20−アルキル)(C1〜C20−アルケニル)またはN−(C1〜C20−アルキル)(アリール)もしくはN−(C1〜C20−アルケニル)(アリール)、
(c)NR2−D7−NR2H、または
(d)NR2−D7−NR2−CH2−CH2−CO−NH−(C1〜C20−アルキル)もしくはNR2−D7−NR2−CH2−CH2−CO−NH−(C1〜C20−アルケニル)もしくはNR2−D7−NR2−CH2−CH2−CO−NH−アリール、
D6またはR2のうちの少なくとも1つがC5〜C20芳香族部分を含む)。
−MAは、水素またはアルカリ金属(好ましくはNaまたはK)であり、
−XAはPまたはSであり、
−d=1〜6、好ましくは2であり、
−RA1は、C1〜C8アルキル基またはヘテロアルキル基、アリール基またはヘテロ芳香族基から選択される。ヘテロアルキル基は、1つまたは複数のヘテロ原子(N、S、O)および1〜12個の炭素を有することになる。炭素環式アリール基は典型的なアリール基、例えばフェニル、ナフチルなどである。ヘテロ芳香族基はまた適切なアリール基であり、1個または複数のN、OまたはS原子および1〜3個の別々のまたは縮合した環を含有し、
−RA2は、Hまたは(−S−RA1’XO3M)から選択され、RA1’はRA1と等しいかまたは異なる。
XAO3S−RA1−SH
XAO3S−RA1−S−S−RA1’−SO3XA
XAO3S−Ar−S−S−Ar−SO3XA
RA1は、上で定義された通りであり、Arはアリールである。
−MPS:3−メルカプト−1−プロパンスルホン酸、ナトリウム塩
(a)WO2010/115796に記載されている通り、少なくとも3つの活性のあるアミノ官能基を含むアミン化合物を、エチレンオキシドと、C3およびC4アルキレンオキシドから選択される少なくとも1つの化合物との混合物と反応させることによって得ることができる抑制化剤。
(CHOH)w (S3b)
(式中、vは3〜8の整数であり、wは5〜10の整数である)。最も好ましい単糖アルコールは、ソルビトール、マンニトール、キシリトール、リビトールおよびイノシトールである。さらなる好ましいポリアルコールは、式(S4a)または(S4b)の単糖である。
CH2OH−(CHOH)y−CO−(CHOH)z−CH2OH (S4b)
(式中、xは4または5の整数であり、y、zは整数であり、y+zは3または4である)。最も好ましい単糖アルコールは、アルドースアロース、アルトロース、ガラクトース、グルコース、グロース、イドース、マンノース、タロース、グルコヘプトース、マンノヘプトースまたはケトースフルクトース、プシコース、ソルボース、タガトース、マンノヘプツロース、セドヘプツロース、タロヘプツロース、アロヘプツロースから選択される。
アジピン酸およびジエチレントリアミン由来のポリアミノアミドC1(分子比18:19)
アジピン酸およびN,N’−ビス−(3−アミノプロピル)−エチレンジアミン由来のポリアミノアミドC2(分子比18:19)
ポリアミノアミドC1および塩化ベンジル由来の官能化ポリアミノアミド1
ポリアミノアミドC1およびスチレンオキシド由来の官能化ポリアミノアミド2
アジピン酸およびジエチレントリアミン(分子比18:19)、POおよび塩化ベンジル由来の官能化ポリアミノアミド3
ポリアミノアミドC2および1−クロロメチルナフタレン由来の官能化ポリアミノアミド4
アジピン酸およびジプロピレントリアミン(分子比18:19)および1−クロロメチルナフタレン由来の官能化ポリアミノアミド5
[(Labor:L1973)]:ピペラジン、キシリレンジアミンおよびメチレンビスアクリルアミド(分子比16.2:9.5:18)由来のポリアミドアミン6
60g/lの銅(硫酸銅として)、10g/lの硫酸、0.150g/lの塩素イオン(HClとして)、0.100g/lのEO/POコポリマー抑制剤、ならびに0.028g/lのSPSおよびDI水を合わせることによって、銅めっき浴を調製した。EO/POコポリマー抑制剤は、分子量<5000g/molおよび末端ヒドロキシ基を有した。さらに、比較例1で調製した、2ml/lの1重量%のポリアミノアミドC1溶液を加えた。
60g/lの銅(硫酸銅として)、10g/lの硫酸、0.150g/lの塩素イオン(HClとして)、0.100g/lのEO/POコポリマー抑制剤、ならびに0.028g/lのSPSおよびDI水を合わせることで銅めっき浴を調製した。EO/POコポリマー抑制剤は、分子量<5000g/molおよび末端ヒドロキシ基を有した。さらに、比較例2で調製した2ml/lの1重量%のポリアミノアミドC2溶液を加えた。
60g/lの銅(硫酸銅として)、10g/lの硫酸、0.150g/lの塩素イオン(HClとして)、0.100g/lのEO/POコポリマー抑制剤、ならびに0.028g/lのSPSおよびDI水を合わせることによって、銅めっき浴を調製した。EO/POコポリマー抑制剤は、分子量<5000g/molおよび末端ヒドロキシ基を有した。さらに、実施例3で調製した、6ml/lの0.26重量%のポリアミノアミド1溶液を加えた。
60g/lの銅(硫酸銅として)、10g/lの硫酸、0.150g/l塩素イオン(HClとして)、0.100g/lのEO/POコポリマー抑制剤、ならびに0.028g/lのSPSおよびDI水を合わせることによって、銅めっき浴を調製した。EO/POコポリマー抑制剤は、分子量<5000g/molおよび末端ヒドロキシ基を有した。さらに、実施例4で調製した、6ml/lの0.33重量%のポリアミノアミド2溶液を加えた。
40g/lの銅(硫酸銅として)、10g/lの硫酸、0.050g/lの塩素イオン(HClとして)、0.100g/lのEO/POコポリマー抑制剤、ならびに0.028g/lのSPSおよびDI水を合わせることによって、銅めっき浴を調製した。EO/POコポリマー抑制剤は、分子量<5000g/molおよび末端ヒドロキシ基を有した。さらに、実施例5で調製した、1.5ml/lの1重量%のポリアミノアミド3溶液を加えた。
60g/lの銅(硫酸銅として)、10g/lの硫酸、0.050g/lの塩素イオン(HClとして)、0.100g/lのEO/POコポリマー抑制剤、ならびに0.028g/lのSPSおよびDI水を合わせることによって、銅めっき浴を調製した。EO/POコポリマー抑制剤は、分子量<5000g/molおよび末端ヒドロキシ基を有した。さらに、実施例6で調製した、2ml/lの1重量%のポリアミノアミド4溶液を加えた。
60g/lの銅(硫酸銅として)、10g/lの硫酸、0.050g/lの塩素イオン(HClとして)、0.100g/lのEO/POコポリマー抑制剤、ならびに0.028g/lのSPSおよびDI水を合わせることによって、銅めっき浴を調製した。EO/POコポリマー抑制剤は、分子量<5000g/molおよび末端ヒドロキシ基を有していた。さらに、実施例7で調製した、2ml/lの1重量%のポリアミノアミド5溶液を加えた。
Claims (18)
- 銅イオン供給源と、少なくとも1つのポリアミノアミドとを含み、
前記ポリアミノアミドが、ポリマー主鎖内にアミドおよびアミン官能基を含み、且つ少なくとも1つの芳香族部分が前記ポリマー主鎖に付加しているか、または前記ポリマー主鎖内に位置している組成物であって、
前記ポリアミノアミドが、式Iで表される構造単位または、
[A] p [B] q [D] r (I)
または完全もしくは部分的なプロトン付加、N−官能化、またはN−四級化によって得ることができるその誘導体を含む組成物
(式中、
Aは、
Bは、化学結合または
Dは、化学結合または
D 1 は、各繰返し単位1〜pに対して、独立して、化学結合または飽和もしくは不飽和のC 1 〜C 20 有機基から選択される二価の基から選択され、
D 2 、D 3 は、独立して、直鎖または分枝のC 1 〜C 10 アルカンジイル(NおよびOから選択されるヘテロ原子で場合によって置換されていてもよい)から選択され、
D 4 は、直鎖または分枝のC 2 〜C 6 アルカンジイル、C 6 〜C 10 のアリールまたはヘテロアリールジラジカル、C 8 〜C 20 アリールアルカンジイル、C 8 〜C 20 ヘテロアリールアルカンジイルから選択され、
D 5 は、直鎖または分枝のC 1 −〜C 7 −アルカンジイル(ヘテロ原子で場合によって置換されていてもよい)から選択され、
R 1 は、各繰返し単位1〜nに対して、独立して、H、C 1 〜C 20 −アルキルおよびC 5 〜C 20 −アリールまたはC 5 〜C 20 −ヘテロアリール(ヒドロキシル、アルコキシまたはアルコキシカルボニルで場合によって置換されていてもよい)から選択され、
nは2〜250の整数であり、
pは2〜150の整数であり、
qは0〜150の整数であり、
rは0〜150の整数であり、
R 1 が、C 5 〜C 20 芳香族部分を含むか、またはポリアミノアミドが、C 5 〜C 20 芳香族部分で官能化および/または四級化されている)。 - ポリアミノアミドが式II
(式中、D1、D2、D3、R1、nおよびpは規定の意味を有し、
E1、E2は、独立して、以下から選択され
(a)求核的に置換可能な脱離基、
(b)NH−(C1〜C20−アルキル)またはNH−(C1〜C20−アルケニル)またはNH−アリール、
(c)H−{NH−[D2−NR1]n−D3−NH}
(d)(C1〜C20−アルキル)−CO−{NH−[D2−NR2]n−D3−NH}、および
(e)(C1〜C20−アルケニル)−CO−{NH−[D2−NR2]n−D3−NH}、
(f)(C1〜C20−アリール)−CO−{NH−[D2−NR2]n−D3−NH}、
R 1 は、C5〜C20芳香族部分を含む)
で表される、請求項1に記載の組成物。 - D1が、C1〜C20アルカンジイル基から選択される、請求項1又は2の何れかに記載の組成物。
- D2およびD3が、独立して(CH2)2および(CH2)3から選択される、請求項1から3のいずれか一項に記載の組成物。
- R1が水素またはメチルである、請求項1から4のいずれか一項に記載の組成物。
- R1が、C5〜C20アリール、C5〜C20ヘテロアリール、C5〜C20アリールアルキルC5〜C20ヘテロアリールアルキルから選択される、請求項1から4のいずれか一項に記載の組成物。
- 前記ポリアミノアミドが、少なくとも1つのポリアルキレンポリアミンを、少なくとも1つのジカルボン酸と反応させることによって得ることができる、請求項1から6のいずれか一項に記載の組成物。
- 少なくとも1つのポリアルキレンポリアミンが、ジエチレントリアミン、トリエチレンテトラミン、テトラエチレンペンタアミン、ペンタエチレンヘキサミン、ジアミノプロピルエチレンジアミン、エチレンプロピレントリアミン、3−(2−アミノエチル)アミノプロピルアミン、ジプロピレントリアミン、ポリエチレンイミンおよびエーテルアミン(H2N−(CH2)2−O−(CH2)2−NH2またはH2N−(CH2)2−O−(CH2)2−O−(CH2)2−NH2およびこれらの混合物から選択される)から選択される、請求項7に記載の組成物。
- 少なくとも1つのジカルボン酸が、シュウ酸、マロン酸、コハク酸、酒石酸、マレイン酸、イタコン酸、グルタル酸、アジピン酸、スベリン酸、セバシン酸、イミノ二酢酸、アスパラギン酸、グルタミン酸、およびこれらの混合物から選択される、請求項7または8に記載の組成物。
- 銅イオン供給源と、少なくとも1つのポリアミノアミドとを含む組成物であって、
前記ポリアミノアミドが、ポリマー主鎖内にアミドおよびアミン官能基を含み、且つ少なくとも1つの芳香族部分が前記ポリマー主鎖に付加しているか、または前記ポリマー主鎖内に位置しており、
前記ポリアミノアミドが、式IIIで表される基
を含む組成物
(式中、
D6は、各繰返し単位1〜sに対して、独立して、飽和、不飽和または芳香族のC1〜C20有機基から選択される二価の基であり、
D7は、直鎖または分枝のC2〜C6アルカンジイル、C6〜C10アリールジラジカル、C8〜C20アリールアルカンジイルから選択され、
R2は、各繰返し単位1〜sに対して、独立して、H、C1〜C20アルキル、C1〜C20アルケニル(ヒドロキシル、アルコキシまたはアルコキシカルボニルで場合によって置換されていてもよい)、またはアリールから選択され、2つのR2は一緒になって環系を形成してもよく、
sは、1〜250の整数であり、
D6、D7またはR2のうちの少なくとも1つが、C5〜C20芳香族部分を含むか、またはポリアミノアミドが、C5〜C20芳香族部分で官能化および/または四級化されている)。 - 式IV
(式中、D6、D7、R 2 、およびsは、規定の意味を有し、
E3、E4は、独立して、以下から選択され
(a)NH−C1〜C20−アルキルもしくはNH−C1〜C20−アルケニルもしくはNH−アリール、
(b)N−(C1〜C20−アルキル)2もしくはN−(C1〜C20−アルケニル)2もしくはN−(アリール)2もしくはN−(C1〜C20−アルキル)(C1〜C20−アルケニル)もしくはN−(C1〜C20−アルキル)(アリール)もしくはN−(C1〜C20−アルケニル)(アリール)、
(c)NR2−D7−NR2H、または
(d)NR2−D7−NR2−CH2−CH2−CO−NH−(C1〜C20−アルキル)もしくはNR2−D7−NR2−CH2−CH2−CO−NH−(C1〜C20−アルケニル)もしくはNR2−D7−NR2−CH2−CH2−CO−NH−アリール、
D6またはR2のうちの少なくとも1つがC5〜C20芳香族部分を含む)。 - 促進化剤をさらに含む、請求項1から11のいずれか一項に記載の組成物。
- 抑制化剤をさらに含む、請求項1から12のいずれか一項に記載の組成物。
- マイクロメートルサイズのフィーチャーを銅で満たすための浴中での、請求項1から13のいずれか一項に記載のポリアミノアミドの使用。
- 前記マイクロメートルサイズのフィーチャーが、シリコン貫通ビアである請求項14に記載の使用。
- a)請求項1から13のいずれかに記載の組成物を含む銅めっき浴を基板と接触させるステップ、
b)前記基板上に金属層を堆積させるのに十分な時間の間、ある電流密度を前記基板に加えるステップ
によって、基板上に金属層を堆積させるための方法。 - 基板がマイクロメートルサイズのフィーチャーを含み、堆積がマイクロメートルサイズのフィーチャーを満たすために実施される、請求項16に記載の方法。
- マイクロメートルサイズのフィーチャーが、1〜500マイクロメートルのサイズおよび/または4以上のアスペクト比を有する、請求項17に記載の方法。
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CN103547631B (zh) | 2016-07-06 |
CN103547631A (zh) | 2014-01-29 |
US9631292B2 (en) | 2017-04-25 |
TW201303089A (zh) | 2013-01-16 |
KR101952568B1 (ko) | 2019-02-27 |
EP2714807B1 (en) | 2019-01-02 |
SG10201604395TA (en) | 2016-07-28 |
WO2012164509A1 (en) | 2012-12-06 |
US20140097092A1 (en) | 2014-04-10 |
SG194983A1 (en) | 2013-12-30 |
IL229465B (en) | 2018-02-28 |
EP2714807A1 (en) | 2014-04-09 |
EP2714807A4 (en) | 2014-11-19 |
IL229465A0 (en) | 2014-01-30 |
TWI573900B (zh) | 2017-03-11 |
RU2013158459A (ru) | 2015-07-20 |
KR20140038484A (ko) | 2014-03-28 |
JP2014523477A (ja) | 2014-09-11 |
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