JP5724068B2 - 新規化合物およびその利用 - Google Patents
新規化合物およびその利用 Download PDFInfo
- Publication number
- JP5724068B2 JP5724068B2 JP2012512604A JP2012512604A JP5724068B2 JP 5724068 B2 JP5724068 B2 JP 5724068B2 JP 2012512604 A JP2012512604 A JP 2012512604A JP 2012512604 A JP2012512604 A JP 2012512604A JP 5724068 B2 JP5724068 B2 JP 5724068B2
- Authority
- JP
- Japan
- Prior art keywords
- copper plating
- group
- plating bath
- tertiary amine
- glycidyl ether
- 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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- 150000001875 compounds Chemical class 0.000 title claims description 60
- 238000007747 plating Methods 0.000 claims description 134
- 239000010949 copper Substances 0.000 claims description 101
- 229910052802 copper Inorganic materials 0.000 claims description 100
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 99
- -1 tertiary amine compound Chemical class 0.000 claims description 63
- 239000000758 substrate Substances 0.000 claims description 48
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 33
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910001431 copper ion Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000002344 surface layer Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 238000011049 filling Methods 0.000 description 16
- 229910052710 silicon Inorganic materials 0.000 description 16
- 239000010703 silicon Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000010410 layer Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 235000012431 wafers Nutrition 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000004566 IR spectroscopy Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000001880 copper compounds Chemical group 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 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
- 238000000151 deposition Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Chemical group 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 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 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 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 description 1
- 229920002359 Tetronic® Polymers 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-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
- RSJOBNMOMQFPKQ-UHFFFAOYSA-L copper;2,3-dihydroxybutanedioate Chemical compound [Cu+2].[O-]C(=O)C(O)C(O)C([O-])=O RSJOBNMOMQFPKQ-UHFFFAOYSA-L 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-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
- 230000008021 deposition Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- FWBOFUGDKHMVPI-UHFFFAOYSA-K dicopper;2-oxidopropane-1,2,3-tricarboxylate Chemical compound [Cu+2].[Cu+2].[O-]C(=O)CC([O-])(C([O-])=O)CC([O-])=O FWBOFUGDKHMVPI-UHFFFAOYSA-K 0.000 description 1
- PEVJCYPAFCUXEZ-UHFFFAOYSA-J dicopper;phosphonato phosphate Chemical compound [Cu+2].[Cu+2].[O-]P([O-])(=O)OP([O-])([O-])=O PEVJCYPAFCUXEZ-UHFFFAOYSA-J 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
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Description
一方、ビアホール内に金属を充填するビアフィリングを用いると、穴が完全に埋まり、しかもフィリングを行なった後のビアホール部分表面が平坦であれば穴の上にまたビアホールを形成できるのでダウンサイジングには非常に有利である。そのため、絶縁体(絶縁層)の平坦化には限界があるコンフォーマルビアホールめっきに代わるものとして、層間の接続穴(ホール)を埋める、いわゆるビアフィリングめっきが多用されるようになってきた。
(1)複素環化合物を、3つ以上のグリシジルエーテル基を有する化合物のグリシジルエーテル基のエポキシ基と反応させることにより得られる第3級アミン化合物。
(1)次式(a)で表されるスルホアルキルスルホン酸およびその塩
(2)次式(b)で表されるビススルホ有機化合物
(3)次式(c)で表されるジチオカルバミン酸誘導体
第3級アミン化合物(IIIa)の合成:
温度計、攪拌機、滴下ロートを備えた反応容器に、グリセリントリグリシジルエーテル(エポキシ当量143g/e.q.)20gを入れ、純水100mLを加えて溶解させた後、0℃に冷却して、ピロリジン10.2gを反応温度が30℃以内になるようにゆっくり加えた。その後、室温まで昇温し、2時間反応させ、NMRにより、エポキシド由来のシグナル(2.54、2.71、3.08ppm)の消失を確認した。次に、減圧濃縮して反応溶媒および過剰のピロリジンを除去し、第3級アミン化合物を29.9g得た。
第4級アンモニウム化合物(IVa)の合成:
温度計、攪拌機、滴下ロート、ジムロート冷却器を備えた反応容器に、上記実施例1で得られた第3級アミン化合物(IIIa)29.9gを入れ、アセトニトリル100mLを加えて完全に溶解した後、ヨウ化メチル17.4mLを加え、12時間加熱還流して反応させた。次に、減圧濃縮して反応溶媒および過剰のヨウ化メチルを除去し、第4級アンモニウム化合物を得た。
第3級アミン化合物(IIIj)の合成:
実施例1に従い、ソルビトールヘキサグリシジルエーテル(エポキシ当量170g/e.q.)20gとピペリジン10.4gを反応させ、NMRにより、エポキシド由来のシグナル(2.54、2.71、3.08ppm)の消失を確認し、第3級アミン化合物を30.0g得た。
第4級アンモニウム化合物(IVt)の合成:
実施例2に従い、上記実施例3で得られた第3級アミン化合物(IIIj)30.0gと塩化アリル19.2mLを反応させ、第4級アンモニウム化合物を39.0g得た。
樹脂基板への銅めっき:
無電解銅めっきにてシード層形成した、直径70μm、深さ40μmのブラインドビアホール(アスペクト比0.57)を有するエポキシ樹脂基板に、実施例1で合成した第3級アミン化合物(IIIa)を添加した以下の組成の銅めっき浴を用い、以下の条件で電気銅めっきを施した。
硫酸銅5水和物:230g/L
硫酸(98%):50g/L
塩素:40mg/L
第3級アミン化合物(IIIa):100mg/L
SPS(*):1mg/L
*ビス3−(スルホプロピル)ジスルフィド
(電気銅めっき条件)
めっき温度:25℃
陰極電流密度:2A/dm2
めっき時間:35分
撹拌:エア撹拌
樹脂基板への銅めっき:
無電解銅めっきにてシード層形成した、直径70μm、深さ40μmのブラインドビアホール(アスペクト比0.57)を有するエポキシ樹脂基板に、実施例2で合成した第4級アンモニウム化合物(IVa)を添加した以下の組成の銅めっき浴を用い、以下の条件で電気銅めっきを施した。
硫酸銅5水和物:230g/L
硫酸(98%):50g/L
塩素:40mg/L
第4級アンモニウム化合物(IVa):100mg/L
SPS(*):1mg/L
*ビス3−(スルホプロピル)ジスルフィド
(電気銅めっき条件)
めっき温度:25℃
陰極電流密度:2A/dm2
めっき時間:25分または35分
撹拌:エア撹拌
樹脂基板への銅めっき(1):
銅めっき浴に添加された第3級アミン化合物(IIIa)100mg/LをヤーヌスグリンB 4mg/LおよびPEG4000 100mg/Lにする以外は実施例5と同様にして樹脂基板に電気銅めっきを施した。
樹脂基板への銅めっき(2):
銅めっき浴に添加された第3級アミン化合物(IIIa)100mg/Lを以下の式で示されるポリエチレングリコール(9重合物)とジメチルアミンおよび塩化アリルからなる第4級アンモニウム化合物100mg/Lにする以外は実施例5と同様にして樹脂基板に電気銅めっきを施した。
銅めっきの評価:
実施例5において電気銅めっきを施した樹脂基板の断面写真を図1(めっき時間35分)に、実施例6において電気銅めっきを施した樹脂基板の断面写真を図2(Aはめっき時間35分、Bは25分)示した。また、比較例1、2において電気銅めっきを施した樹脂基板の断面写真を図3(Cは比較例1、Dは比較例2、めっき時間は共に35分)に示した。実施例5および実施例6は、比較例1、2に比べ、良好なフィリング性能を発揮した。特に図2のBから、実施例6ではめっき時間が25分で完全にビア充填されており、表層めっき厚が9.1μmと非常に薄いめっき厚でのフィリングが可能であることがわかった。これにより本発明がファインパターン回路への適用が可能であることが示された。
シリコンウエハ基板への銅めっき:
真空スパッタでCuのシード層形成した、直径20μm、深さ110μmのブラインドビアホール(アスペクト比5.5)を有するシリコンウエハ基板に、実施例3で合成した第3級アミン化合物(IIIj)を添加した以下の組成の銅めっき浴を用い、以下の条件で電気銅めっきを施した。
硫酸銅5水和物:250g/L
硫酸(98%):30g/L
塩素:40mg/L
第3級アミン化合物(IIIj):10mg/L
SPS(*):1mg/L
*ビス3−(スルホプロピル)ジスルフィド
(電気銅めっき条件)
めっき温度:25℃
陰極電流密度:0.4A/dm2
めっき時間:80分
撹拌:スキージ撹拌
Claims (14)
- 一般式(II)
で表される複素環化合物を、3つ以上のグリシジルエーテル基を有し、一般式(I)
で表される化合物のグリシジルエーテル基のエポキシ基と、室温以下で反応させることにより得られる第3級アミン化合物。 - 請求項1記載の第3級アミン化合物を、第4級化して得られる第4級アンモニウム化合物。
- 一般式(II)
で表される複素環化合物を、3つ以上のグリシジルエーテル基を有し、一般式(I)
で表される化合物のグリシジルエーテル基のエポキシ基と、室温以下で反応させることを特徴とする第3級アミン化合物の製造方法。 - 請求項3記載の第3級アミン化合物の製造方法において製造された第3級アミン化合物を、第4級化試薬と反応させることを特徴とする第4級アンモニウム化合物の製造方法。
- 請求項1記載の第3級アミン化合物および請求項2記載の第4級アンモニウム化合物からなる群より選ばれる化合物の1種または2種以上を含有することを特徴とする銅めっき浴用添加剤。
- 請求項1記載の第3級アミン化合物および請求項2記載の第4級アンモニウム化合物からなる群より選ばれる化合物の1種または2種以上を含有することを特徴とする銅めっき浴。
- 銅めっき浴が、10〜80g/Lの銅イオンおよび5〜200g/Lの有機酸または無機酸を含有するものである請求項6記載の銅めっき浴。
- 銅めっき浴が、請求項1記載の第3級アミン化合物および請求項2記載の第4級アンモニウム化合物からなる群より選ばれる化合物の1種または2種以上を0.1〜1000mg/L含有するものである請求項6または7に記載の銅めっき浴。
- 銅めっき浴が、更に、スルホアルキルスルホン酸またはその塩、ビススルホ有機化合物およびジチオカルバミン酸誘導体からなる群より選ばれる1種または2種以上を含有し、かつ該成分の濃度が0.1〜200mg/Lである請求項6〜8のいずれかに記載の銅めっき浴。
- 酸性である請求項6〜9のいずれかに記載の銅めっき浴。
- 基板を請求項6〜10のいずれかに記載の銅めっき浴でめっきすることを特徴とする銅めっき方法。
- 基板が、アスペクト比1以上であるブラインドビアホールを有するものである請求項11記載の銅めっき方法。
- 基板が、アスペクト比2以上であるスルーホールを有するものである請求項11または12に記載の銅めっき方法。
- 表層めっき厚が15μm以下となるように行う請求項11ないし13のいずれかに記載の銅めっき方法。
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WO2023074223A1 (ja) | 2021-10-26 | 2023-05-04 | 株式会社Jcu | 被めっき物中の銅結晶粒を粗大化する方法および銅めっき膜中の銅結晶粒を粗大化した銅めっき膜 |
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US8747643B2 (en) * | 2011-08-22 | 2014-06-10 | Rohm And Haas Electronic Materials Llc | Plating bath and method |
US9273407B2 (en) | 2014-03-17 | 2016-03-01 | Hong Kong Applied Science and Technology Research Institute Company Limited | Additive for electrodeposition |
CN106574390A (zh) * | 2014-04-25 | 2017-04-19 | 株式会社杰希优 | 铜的高速填充方法 |
FR3033560A1 (fr) * | 2015-03-09 | 2016-09-16 | Ifp Energies Now | Nouvelles polyetheralcanolamines tertiaires, leur procede de synthese et leur utilisation pour l'elimination selective du sulfure d'hydrogene d'un effluent gazeux comprenant du dioxyde de carbone |
ES2681836T3 (es) * | 2015-09-10 | 2018-09-17 | Atotech Deutschland Gmbh | Composición de baño para chapado de cobre |
JP7114216B2 (ja) * | 2016-10-21 | 2022-08-08 | 住友金属鉱山株式会社 | めっき液、めっき膜の製造方法 |
CN110684995A (zh) * | 2018-07-04 | 2020-01-14 | 深圳海恩特科技有限公司 | 电镀整平剂及其电镀溶液 |
JP7208913B2 (ja) * | 2018-08-28 | 2023-01-19 | 株式会社Jcu | 硫酸銅めっき液およびこれを用いた硫酸銅めっき方法 |
CN109972180B (zh) * | 2019-04-12 | 2020-12-18 | 博敏电子股份有限公司 | 2,2'-二硫代二吡啶的新用途及采用其的电镀填孔添加剂及采用该添加剂的电镀方法 |
CN110016699B (zh) * | 2019-05-29 | 2021-05-04 | 广州旗泽科技有限公司 | 一种电镀铜填孔整平剂及其制备方法和应用 |
CN110331422B (zh) * | 2019-08-16 | 2021-02-12 | 国网河南省电力公司桐柏县供电公司 | 一种陶瓷基板电镀铜层增厚方法 |
CN112030199B (zh) * | 2020-08-27 | 2021-11-12 | 江苏艾森半导体材料股份有限公司 | 一种用于先进封装的高速电镀铜添加剂及电镀液 |
US20240132453A1 (en) * | 2021-02-15 | 2024-04-25 | Adeka Corporation | Additive for electroplating solution, electroplating solution, electroplating method, and method of producing metal layer |
CN113802158B (zh) * | 2021-10-21 | 2023-06-20 | 东莞市康迈克电子材料有限公司 | 一种电镀液及其应用、镀铜工艺及镀件 |
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JP2004137588A (ja) * | 2002-10-21 | 2004-05-13 | Nikko Materials Co Ltd | 特定骨格を有する四級アミン化合物及び有機硫黄化合物を添加剤として含む銅電解液並びにそれにより製造される電解銅箔 |
JP2007031834A (ja) * | 2005-07-08 | 2007-02-08 | Rohm & Haas Electronic Materials Llc | メッキ法 |
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JPH07159915A (ja) | 1993-12-03 | 1995-06-23 | Mitsubishi Paper Mills Ltd | ハロゲン化銀写真感光材料 |
US8268157B2 (en) * | 2010-03-15 | 2012-09-18 | Rohm And Haas Electronic Materials Llc | Plating bath and method |
US8262895B2 (en) * | 2010-03-15 | 2012-09-11 | Rohm And Haas Electronic Materials Llc | Plating bath and method |
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US3329674A (en) * | 1963-11-01 | 1967-07-04 | Thiokol Chemical Corp | Aziridinyl derivatives of polyfunctional epoxides |
JPS53101380A (en) * | 1977-01-14 | 1978-09-04 | Sankyo Co Ltd | Piperidine derivatives |
WO2002090623A1 (fr) * | 2001-05-09 | 2002-11-14 | Ebara-Udylite Co., Ltd. | Bain galvanoplastique et procede pour substrat de galvanoplastie faisant appel audit bain |
JP2004137588A (ja) * | 2002-10-21 | 2004-05-13 | Nikko Materials Co Ltd | 特定骨格を有する四級アミン化合物及び有機硫黄化合物を添加剤として含む銅電解液並びにそれにより製造される電解銅箔 |
JP2007031834A (ja) * | 2005-07-08 | 2007-02-08 | Rohm & Haas Electronic Materials Llc | メッキ法 |
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WO2023074223A1 (ja) | 2021-10-26 | 2023-05-04 | 株式会社Jcu | 被めっき物中の銅結晶粒を粗大化する方法および銅めっき膜中の銅結晶粒を粗大化した銅めっき膜 |
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US20130043137A1 (en) | 2013-02-21 |
KR20130092994A (ko) | 2013-08-21 |
KR101549297B1 (ko) | 2015-09-01 |
SG185016A1 (en) | 2012-11-29 |
CN102906078A (zh) | 2013-01-30 |
CN102906078B (zh) | 2015-12-16 |
WO2011135716A1 (ja) | 2011-11-03 |
TW201136893A (en) | 2011-11-01 |
JPWO2011135716A1 (ja) | 2013-08-01 |
US9321741B2 (en) | 2016-04-26 |
TWI477486B (zh) | 2015-03-21 |
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