TWI539036B - 包含平整劑之金屬電鍍用組合物 - Google Patents
包含平整劑之金屬電鍍用組合物 Download PDFInfo
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- TWI539036B TWI539036B TW100119130A TW100119130A TWI539036B TW I539036 B TWI539036 B TW I539036B TW 100119130 A TW100119130 A TW 100119130A TW 100119130 A TW100119130 A TW 100119130A TW I539036 B TWI539036 B TW I539036B
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- 229910052751 metal Inorganic materials 0.000 title claims description 55
- 239000002184 metal Substances 0.000 title claims description 55
- 239000000203 mixture Substances 0.000 title claims description 50
- 238000009713 electroplating Methods 0.000 title description 54
- -1 imidazolium compound Chemical class 0.000 claims description 75
- 239000000758 substrate Substances 0.000 claims description 69
- 238000007747 plating Methods 0.000 claims description 55
- 239000003112 inhibitor Substances 0.000 claims description 36
- 239000000654 additive Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 19
- 230000000996 additive effect Effects 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 238000000151 deposition Methods 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000962 organic group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 229920000768 polyamine Polymers 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910001431 copper ion Inorganic materials 0.000 claims description 2
- 238000005227 gel permeation chromatography Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- 150000004010 onium ions Chemical class 0.000 claims 1
- 239000010949 copper Substances 0.000 description 67
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 59
- 229910052802 copper Inorganic materials 0.000 description 58
- 150000001875 compounds Chemical class 0.000 description 57
- 239000003795 chemical substances by application Substances 0.000 description 54
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 22
- 235000012431 wafers Nutrition 0.000 description 21
- 238000001878 scanning electron micrograph Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 17
- 125000002947 alkylene group Chemical group 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 150000003141 primary amines Chemical group 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 230000007547 defect Effects 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 238000011049 filling Methods 0.000 description 13
- 229910021645 metal ion Inorganic materials 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 229920005862 polyol Polymers 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000004065 semiconductor Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000003792 electrolyte Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 238000007689 inspection Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 125000003172 aldehyde group Chemical group 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920002873 Polyethylenimine Polymers 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 150000002373 hemiacetals Chemical class 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000007858 starting material Substances 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
- 239000011800 void material Substances 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 3
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000005349 anion exchange Methods 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 229940015043 glyoxal Drugs 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 150000002772 monosaccharides Chemical class 0.000 description 3
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-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
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003586 protic polar solvent Substances 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-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
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- 239000005700 Putrescine Substances 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
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- 239000000956 alloy Substances 0.000 description 2
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- 239000003957 anion exchange resin Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
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- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- BSXVKCJAIJZTAV-UHFFFAOYSA-L copper;methanesulfonate Chemical compound [Cu+2].CS([O-])(=O)=O.CS([O-])(=O)=O BSXVKCJAIJZTAV-UHFFFAOYSA-L 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
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- 239000000178 monomer Substances 0.000 description 2
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 2
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- 108010094020 polyglycine Proteins 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 1
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- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
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- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- XPSMITSOZMLACW-UHFFFAOYSA-N 2-(4-aminophenyl)-n-(benzenesulfonyl)acetamide Chemical compound C1=CC(N)=CC=C1CC(=O)NS(=O)(=O)C1=CC=CC=C1 XPSMITSOZMLACW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 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
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Classifications
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- 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
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0616—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
-
- 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
-
- 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
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/30—Electroplating: Baths therefor from solutions of tin
- C25D3/32—Electroplating: Baths therefor from solutions of tin characterised by the organic bath constituents used
-
- 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
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/56—Electroplating: Baths therefor from solutions of alloys
- C25D3/58—Electroplating: Baths therefor from solutions of alloys containing more than 50% by weight of copper
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D5/00—Electroplating characterised by the process; Pretreatment or after-treatment of workpieces
- C25D5/02—Electroplating of selected surface areas
-
- 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
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrochemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Electroplating And Plating Baths Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35004510P | 2010-06-01 | 2010-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201211321A TW201211321A (en) | 2012-03-16 |
| TWI539036B true TWI539036B (zh) | 2016-06-21 |
Family
ID=45066252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100119130A TWI539036B (zh) | 2010-06-01 | 2011-05-31 | 包含平整劑之金屬電鍍用組合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9683302B2 (enExample) |
| EP (1) | EP2576696B1 (enExample) |
| JP (1) | JP5933532B2 (enExample) |
| KR (3) | KR101829866B1 (enExample) |
| CN (1) | CN102939339B (enExample) |
| IL (1) | IL223183B (enExample) |
| MY (1) | MY164464A (enExample) |
| RU (1) | RU2603675C2 (enExample) |
| SG (2) | SG185736A1 (enExample) |
| TW (1) | TWI539036B (enExample) |
| WO (1) | WO2011151785A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI658176B (zh) * | 2016-09-22 | 2019-05-01 | 美商麥克達米德恩索龍股份有限公司 | 積體電路之晶圓級封裝中的銅沉積 |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY170653A (en) | 2010-12-21 | 2019-08-23 | Basf Se | Composition for metal electroplating comprising leveling agent |
| US9243339B2 (en) * | 2012-05-25 | 2016-01-26 | Trevor Pearson | Additives for producing copper electrodeposits having low oxygen content |
| EP3068819B1 (en) | 2013-11-06 | 2019-03-27 | Rohm and Haas Electronic Materials LLC | Nitrogen containing polymers as levelers |
| EP3177671A1 (en) * | 2014-08-06 | 2017-06-14 | Basf Se | Improved process for preparing polymeric, ionic imidazolium compounds |
| US10221281B2 (en) * | 2014-08-06 | 2019-03-05 | Basf Se | Process for preparing polymeric, ionic imidazolium compounds of high molecular weight |
| JP2018517793A (ja) | 2015-04-28 | 2018-07-05 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | 電気めっき浴用の添加剤としてのビス無水物及びジアミンの反応生成物 |
| TWI608132B (zh) | 2015-08-06 | 2017-12-11 | 羅門哈斯電子材料有限公司 | 自含有吡啶基烷基胺及雙環氧化物之反應產物的銅電鍍覆浴液電鍍覆光阻劑限定之特徵的方法 |
| US10006136B2 (en) | 2015-08-06 | 2018-06-26 | Dow Global Technologies Llc | Method of electroplating photoresist defined features from copper electroplating baths containing reaction products of imidazole compounds, bisepoxides and halobenzyl compounds |
| US10100421B2 (en) * | 2015-08-06 | 2018-10-16 | Dow Global Technologies Llc | Method of electroplating photoresist defined features from copper electroplating baths containing reaction products of imidazole and bisepoxide compounds |
| US9932684B2 (en) | 2015-08-06 | 2018-04-03 | Rohm And Haas Electronic Materials Llc | Method of electroplating photoresist defined features from copper electroplating baths containing reaction products of alpha amino acids and bisepoxides |
| US20170067173A1 (en) * | 2015-09-09 | 2017-03-09 | Rohm And Haas Electronic Materials Llc | Acid copper electroplating bath and method for electroplating low internal stress and good ductility copper deposits |
| AU2016355706B2 (en) * | 2015-11-20 | 2020-02-06 | Hexion Inc. | Chemical products for surface protection |
| US10100420B2 (en) | 2015-12-29 | 2018-10-16 | Hong Kong Applied Science and Technology Research Institute Company Limtied | Plating leveler for electrodeposition of copper pillar |
| US10519557B2 (en) * | 2016-02-12 | 2019-12-31 | Macdermid Enthone Inc. | Leveler compositions for use in copper deposition in manufacture of microelectronics |
| US10190228B2 (en) * | 2016-03-29 | 2019-01-29 | Rohm And Haas Electronic Materials Llc | Copper electroplating baths and electroplating methods capable of electroplating megasized photoresist defined features |
| WO2018073011A1 (en) | 2016-10-20 | 2018-04-26 | Basf Se | Composition for metal plating comprising suppressing agent for void free submicron feature filling |
| US11926918B2 (en) | 2016-12-20 | 2024-03-12 | Basf Se | Composition for metal plating comprising suppressing agent for void free filing |
| WO2018219848A1 (en) | 2017-06-01 | 2018-12-06 | Basf Se | Composition for tin alloy electroplating comprising leveling agent |
| EP3679179B1 (en) | 2017-09-04 | 2023-10-11 | Basf Se | Composition for metal electroplating comprising leveling agent |
| EP3511444B1 (en) * | 2018-01-16 | 2020-07-22 | ATOTECH Deutschland GmbH | Metal or metal alloy deposition composition and plating compound |
| KR102483615B1 (ko) * | 2018-01-24 | 2023-01-03 | 삼성전기주식회사 | 비스-아릴 암모늄 화합물을 포함하는 도금용 평탄제 및 이를 이용한 구리 도금 방법 |
| CN119121333A (zh) * | 2018-04-19 | 2024-12-13 | 巴斯夫欧洲公司 | 用于钴或钴合金电镀的组合物 |
| KR102662397B1 (ko) * | 2018-10-23 | 2024-05-02 | 솔브레인 주식회사 | 전기도금 조성물 및 전기도금 방법 |
| US20220333262A1 (en) | 2019-09-27 | 2022-10-20 | Basf Se | Composition for copper bump electrodeposition comprising a leveling agent |
| CN114450438A (zh) | 2019-09-27 | 2022-05-06 | 巴斯夫欧洲公司 | 用于铜凸块电沉积的包含流平剂的组合物 |
| CN110938847B (zh) * | 2019-10-30 | 2021-11-12 | 苏州清飙科技有限公司 | 电镀铜整平剂及其制备方法、以及电镀液 |
| WO2021197950A1 (en) | 2020-04-03 | 2021-10-07 | Basf Se | Composition for copper bump electrodeposition comprising a polyaminoamide type leveling agent |
| EP3922662A1 (en) | 2020-06-10 | 2021-12-15 | Basf Se | Polyalkanolamine |
| JP7781850B2 (ja) | 2020-07-13 | 2025-12-08 | ビーエーエスエフ ソシエタス・ヨーロピア | コバルトシード上の銅電気メッキ用組成物 |
| KR102339868B1 (ko) * | 2021-07-30 | 2021-12-16 | 와이엠티 주식회사 | 레벨링제 및 이를 포함하는 비아홀 충진을 위한 전기도금 조성물 |
| WO2023052254A1 (en) | 2021-10-01 | 2023-04-06 | Basf Se | Composition for copper electrodeposition comprising a polyaminoamide type leveling agent |
| KR20250036166A (ko) | 2022-07-07 | 2025-03-13 | 바스프 에스이 | 구리 나노트윈 전착을 위한 폴리아미노아미드 유형 화합물을 포함하는 조성물의 용도 |
| KR20250124348A (ko) | 2022-12-19 | 2025-08-19 | 바스프 에스이 | 구리 나노트윈 전착용 조성물 |
| WO2025026863A1 (en) | 2023-08-03 | 2025-02-06 | Basf Se | Composition for copper electroplating on a metal seed |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3108006A (en) * | 1959-07-13 | 1963-10-22 | M & T Chemicals Inc | Plating on aluminum |
| JPS55122892A (en) * | 1979-03-16 | 1980-09-20 | Furukawa Electric Co Ltd:The | Plating bath for tin, tin-lead alloy |
| US5077414A (en) * | 1990-03-29 | 1991-12-31 | E. I. Du Pont De Nemours And Company | Preparation of 1,3-disubstituted imidazolium salts |
| JPH04202305A (ja) * | 1990-11-29 | 1992-07-23 | Sanyo Chem Ind Ltd | ４級塩変性スチレン系樹脂 |
| JPH0754188A (ja) * | 1993-08-06 | 1995-02-28 | Nippon Steel Corp | アルミ−クロム合金めっき鋼板の製造法 |
| US5607570A (en) * | 1994-10-31 | 1997-03-04 | Rohbani; Elias | Electroplating solution |
| JP3655388B2 (ja) * | 1996-04-08 | 2005-06-02 | ディップソール株式会社 | 錫めっき及び錫−鉛合金めっき用非酸性浴、及び該めっき浴を用いためっき方法 |
| US6024857A (en) | 1997-10-08 | 2000-02-15 | Novellus Systems, Inc. | Electroplating additive for filling sub-micron features |
| FR2773991B1 (fr) | 1998-01-26 | 2000-05-26 | Oreal | Utilisation a titre d'agent protecteur des fibres keratiniques de polymeres de polyammonium quaternaire heterocyclique et compositions cosmetiques |
| JP2001073182A (ja) | 1999-07-15 | 2001-03-21 | Boc Group Inc:The | 改良された酸性銅電気メッキ用溶液 |
| US20050006245A1 (en) * | 2003-07-08 | 2005-01-13 | Applied Materials, Inc. | Multiple-step electrodeposition process for direct copper plating on barrier metals |
| WO2001096632A2 (en) * | 2000-06-15 | 2001-12-20 | Applied Materials, Inc. | A method and apparatus for conditioning electrochemical baths in plating technology |
| US6610192B1 (en) | 2000-11-02 | 2003-08-26 | Shipley Company, L.L.C. | Copper electroplating |
| US8002962B2 (en) | 2002-03-05 | 2011-08-23 | Enthone Inc. | Copper electrodeposition in microelectronics |
| US7316772B2 (en) * | 2002-03-05 | 2008-01-08 | Enthone Inc. | Defect reduction in electrodeposited copper for semiconductor applications |
| US20030201191A1 (en) * | 2002-04-29 | 2003-10-30 | Applied Materials, Inc. | Electrochemical method for direct organic additives analysis in copper baths |
| JP2004217565A (ja) | 2003-01-15 | 2004-08-05 | Shikoku Chem Corp | 殺菌剤及び活性汚泥のバルキングならびにスカム解消方法 |
| US7128822B2 (en) | 2003-06-04 | 2006-10-31 | Shipley Company, L.L.C. | Leveler compounds |
| DE10333239A1 (de) * | 2003-07-21 | 2005-03-10 | Basf Ag | Verfahren zur Herstellung von gereinigten 1,3- substituierten Imidazoliumsalzen |
| TW200613586A (en) * | 2004-07-22 | 2006-05-01 | Rohm & Haas Elect Mat | Leveler compounds |
| JP4973829B2 (ja) * | 2004-07-23 | 2012-07-11 | 上村工業株式会社 | 電気銅めっき浴及び電気銅めっき方法 |
| US7771579B2 (en) | 2004-12-03 | 2010-08-10 | Taiwan Semiconductor Manufacturing Co. | Electro chemical plating additives for improving stress and leveling effect |
| US7662981B2 (en) | 2005-07-16 | 2010-02-16 | Rohm And Haas Electronic Materials Llc | Leveler compounds |
| KR101223386B1 (ko) * | 2006-09-25 | 2013-01-16 | 에스케이종합화학 주식회사 | 이미다졸린계 부식억제제 조성물 |
| RU2334831C2 (ru) * | 2006-10-31 | 2008-09-27 | Федеральное государственное унитарное предприятие "Калужский научно-исследовательский институт телемеханических устройств" | Электролит меднения |
| JP2008195990A (ja) * | 2007-02-09 | 2008-08-28 | Dipsol Chem Co Ltd | 電気アルミニウムめっき浴及びそれを用いためっき方法 |
| CN101896467A (zh) * | 2007-12-12 | 2010-11-24 | 巴斯夫欧洲公司 | 生产二取代的咪唑*盐的方法 |
| EP2093278A1 (de) * | 2008-02-05 | 2009-08-26 | Evonik Goldschmidt GmbH | Performance-Additive zur Verbesserung der Benetzungseigenschaften von ionischen Flüssigkeiten auf festen Oberflächen |
| EP2199315B1 (en) | 2008-12-19 | 2013-12-11 | Basf Se | Composition for metal electroplating comprising leveling agent |
| KR101701526B1 (ko) | 2008-12-22 | 2017-02-01 | 바스프 에스이 | 중합체 이온성 이미다졸륨 화합물의 제조 방법 |
-
2011
- 2011-05-31 KR KR1020137000075A patent/KR101829866B1/ko active Active
- 2011-05-31 US US13/701,217 patent/US9683302B2/en active Active
- 2011-05-31 WO PCT/IB2011/052385 patent/WO2011151785A1/en not_active Ceased
- 2011-05-31 TW TW100119130A patent/TWI539036B/zh active
- 2011-05-31 JP JP2013513029A patent/JP5933532B2/ja active Active
- 2011-05-31 SG SG2012086377A patent/SG185736A1/en unknown
- 2011-05-31 SG SG10201504251WA patent/SG10201504251WA/en unknown
- 2011-05-31 KR KR1020187004069A patent/KR101891473B1/ko active Active
- 2011-05-31 EP EP11789339.6A patent/EP2576696B1/en active Active
- 2011-05-31 KR KR1020187023375A patent/KR101955869B1/ko active Active
- 2011-05-31 MY MYPI2012005096A patent/MY164464A/en unknown
- 2011-05-31 RU RU2012157535/05A patent/RU2603675C2/ru not_active IP Right Cessation
- 2011-05-31 CN CN201180027324.9A patent/CN102939339B/zh active Active
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2012
- 2012-11-22 IL IL223183A patent/IL223183B/en active IP Right Grant
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI658176B (zh) * | 2016-09-22 | 2019-05-01 | 美商麥克達米德恩索龍股份有限公司 | 積體電路之晶圓級封裝中的銅沉積 |
Also Published As
| Publication number | Publication date |
|---|---|
| US9683302B2 (en) | 2017-06-20 |
| CN102939339A (zh) | 2013-02-20 |
| EP2576696A1 (en) | 2013-04-10 |
| US20130068626A1 (en) | 2013-03-21 |
| JP2013527325A (ja) | 2013-06-27 |
| KR101955869B1 (ko) | 2019-03-07 |
| EP2576696B1 (en) | 2017-10-04 |
| KR20180017244A (ko) | 2018-02-20 |
| KR20130112018A (ko) | 2013-10-11 |
| IL223183A0 (en) | 2013-02-03 |
| WO2011151785A1 (en) | 2011-12-08 |
| JP5933532B2 (ja) | 2016-06-15 |
| CN102939339B (zh) | 2016-02-17 |
| SG185736A1 (en) | 2012-12-28 |
| RU2603675C2 (ru) | 2016-11-27 |
| KR101891473B1 (ko) | 2018-08-27 |
| EP2576696A4 (en) | 2014-07-16 |
| KR101829866B1 (ko) | 2018-02-20 |
| TW201211321A (en) | 2012-03-16 |
| IL223183B (en) | 2018-03-29 |
| MY164464A (en) | 2017-12-15 |
| RU2012157535A (ru) | 2014-07-20 |
| SG10201504251WA (en) | 2015-07-30 |
| KR20180094140A (ko) | 2018-08-22 |
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