US20230025950A1 - Copper electroplating solution, method of producing same, and copper electroplating method - Google Patents

Copper electroplating solution, method of producing same, and copper electroplating method Download PDF

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Publication number
US20230025950A1
US20230025950A1 US17/781,949 US202017781949A US2023025950A1 US 20230025950 A1 US20230025950 A1 US 20230025950A1 US 202017781949 A US202017781949 A US 202017781949A US 2023025950 A1 US2023025950 A1 US 2023025950A1
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Prior art keywords
copper electroplating
copper
mass
electroplating solution
component
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US17/781,949
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English (en)
Inventor
Takuya Takahashi
Shinya ISHIWATA
Tomoko HATSUKADE
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Adeka Corp
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Adeka Corp
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Assigned to ADEKA CORPORATION reassignment ADEKA CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TAKAHASHI, TAKUYA, HATSUKADE, Tomoko, ISHIWATA, Shinya
Publication of US20230025950A1 publication Critical patent/US20230025950A1/en
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    • 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
    • C25D5/00—Electroplating characterised by the process; Pretreatment or after-treatment of workpieces
    • C25D5/02—Electroplating of selected surface areas
    • 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

Definitions

  • the present invention relates to a copper electroplating solution comprising sulfuric acid and a compound having a specific structure, a method of producing the copper electroplating solution, and to a copper electroplating method comprising using the copper electroplating solution.
  • Patent Literature 1 As a copper electroplating solution that has heretofore been known, for example, in Patent Literature 1, there is a disclosure of a copper plating bath containing 0.8 M copper sulfate and 0.5 M isethionic acid. In addition, in Patent Literature 2, there is a disclosure of a copper plating bath containing copper oxide and isethionic acid, and in Patent Literature 3, there is a disclosure of a copper plating bath containing copper sulfate pentahydrate, sulfuric acid, hydrochloric acid, and a trace amount of isethionic acid.
  • a copper electroplating solution comprising the following components: (A) a sulfate ion; (B) a compound represented by the following general formula (1); and (C) a copper ion, wherein the copper electroplating solution has a content of the component (B) of from 0.3 part by mass to 50 parts by mass and a content of the component (C) of from 5 parts by mass to 50 parts by mass with respect to 100 parts by mass of a content of the component (A):
  • the copper layer that has a high purity and is excellent in surface flatness can be obtained.
  • FIG. 1 is a schematic sectional view of a substrate to be plated after the formation of a copper layer on the surface of the substrate to be plated by a copper electroplating method in an evaluation test.
  • a copper electroplating solution of the present invention is a copper electroplating solution containing, as essential components, the following components: (A) a sulfate ion (hereinafter also referred to as “component (A)”); (B) a compound represented by the general formula (1) (hereinafter also referred to as “component (B)”); and (C) a copper ion (hereinafter also referred to as “component (C)”).
  • component (A) a sulfate ion
  • component (B) a compound represented by the general formula (1)
  • component (C) a copper ion
  • a supply source for the component (A) is not particularly limited, but for example, at least one kind selected from the group consisting of: sulfuric acid; copper sulfate; iron sulfate; lead sulfate; silver sulfate; calcium sulfate; potassium sulfate; sodium sulfate; barium sulfate; magnesium sulfate; aluminum sulfate; nickel sulfate; a mixture thereof; and a hydrate thereof may be used.
  • Those supply sources for the component (A) may be used alone or in combination thereof.
  • the supply source for the component (A) to be used is preferably at least one kind of sulfuric acid, copper sulfate, or copper sulfate pentahydrate, more preferably a combination of sulfuric acid and copper sulfate or copper sulfate pentahydrate because a copper layer that has a higher purity and is excellent in surface flatness can be obtained.
  • the component (B) is a compound represented by the following general formula (1):
  • R 1 and R 2 each independently represent a hydrogen atom, a sodium atom, a potassium atom, or an alkyl group having 1 to 5 carbon atoms, and “n” represents 1 or 2.
  • R 1 and R 2 each independently represent a hydrogen atom, a sodium atom, a potassium atom, or an alkyl group having 1 to 5 carbon atoms.
  • Examples of the alkyl group having 1 to 5 carbon atoms represented by each of R 1 and R 2 may include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a pentyl group, and a neopentyl group.
  • R 1 preferably represents a hydrogen atom or a sodium atom, and more preferably represents a hydrogen atom because a copper layer that is more excellent in surface flatness can be obtained.
  • R 2 preferably represents a hydrogen atom.
  • n represents 1 or 2. “n” preferably represents 2 because a copper layer that is more excellent in surface flatness can be obtained.
  • Preferred specific examples of the compound represented by the general formula (1) include the following compounds No. 1 to No. 12.
  • the symbol “Me” represents a methyl group
  • the symbol “Et” represents an ethyl group
  • the symbol “iPr” represents an isopropyl group.
  • the compounds No. 2, No. 7, and No. 8 are preferred, and the compound No. 7 is more preferred.
  • a supply source for the component (C) (copper ion) is not particularly limited, but for example, at least one kind selected from the group consisting of: copper sulfate; copper chloride; copper bromide; copper hydroxide; a mixture thereof; and a hydrate thereof may be used. Those supply sources for the component (C) may be used alone or in combination thereof.
  • the supply source for the component (C) to be used is preferably copper sulfate or copper sulfate pentahydrate because a copper layer that has a higher purity and is excellent in surface flatness can be obtained.
  • the content of the component (B) in the copper electroplating solution is from 0.3 part by mass to 50 parts by mass with respect to 100 parts by mass of the content of the component (A).
  • the content of the component (B) is preferably from 1 part by mass to 30 parts by mass, more preferably from 3 parts by mass to 20 parts by mass with respect to 100 parts by mass of the content of the component (A) because a copper layer that is more excellent in surface flatness can be obtained.
  • the content of the component (C) in the copper electroplating solution is from 5 parts by mass to 50 parts by mass with respect to 100 parts by mass of the content of the component (A).
  • the content of the component (C) is preferably from 10 parts by mass to 40 parts by mass, more preferably from 20 parts by mass to 30 parts by mass with respect to 100 parts by mass of the content of the component (A) because a copper layer that has a higher purity and is excellent in surface flatness can be obtained.
  • the content of the component (B) is preferably from 1 part by mass to 200 parts by mass, more preferably from 5 parts by mass to 100 parts by mass, most preferably from 10 parts by mass to 70 parts by mass with respect to 100 parts by mass of the content of the component (C) because a copper layer that has a higher purity and is excellent in surface flatness can be obtained.
  • the concentration of the component (A) (sulfate ion) in the copper electroplating solution is not particularly limited, but is generally from 10 g/L to 500 g/L, preferably from 50 g/L to 350 g/L, more preferably from 100 g/L to 250 g/L, still more preferably from 110 g/L to 200 g/L.
  • the concentration of the component (B) in the copper electroplating solution is not particularly limited, but is generally from 0.3 g/L to 80 g/L, preferably from 1 g/L to 60 g/L, more preferably from 5 g/L to 40 g/L, still more preferably from 5 g/L to 35 g/L.
  • the concentration of the component (C) in the copper electroplating solution is not particularly limited, but is generally from 5 g/L to 250 g/L, preferably from 10 g/L to 150 g/L, more preferably from 20 g/L to 80 g/L, still more preferably from 25 g/L to 70 g/L.
  • the copper electroplating solution of the present invention may contain, as a component except the above-mentioned component (A) to component (C), a chloride ion source, a plating promoter, a plating inhibitor, or the like
  • the chloride ion source is not particularly limited, but examples thereof include hydrogen chloride and sodium chloride.
  • the concentration of the chloride ion source in the copper electroplating solution is preferably from 5 mg/L to 200 mg/L, more preferably from 20 mg/L to 150 mg/L.
  • the plating promoter is not particularly limited, but examples thereof include compounds represented by the following general formulae (2) to (4).
  • R represents a substituted or unsubstituted alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms
  • Ar represents a substituted or unsubstituted aryl group, such as a substituted or unsubstituted phenyl group or naphthyl group
  • X represents a counterion, such as a sodium or potassium ion.
  • R 21 and R 22 each represent a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 9 carbon atoms that may have a substituent having 1 to 3 carbon atoms, or an aryl group that may have a substituent having 1 to 3 carbon atoms
  • M represents an alkali metal, ammonium, or a monovalent organic ammonium
  • n represents a number of from 1 to 7.
  • SPS sodium 3,3′-dithiobis(1-propanesulfonate)
  • the concentration of such plating promoter in the copper electroplating solution is preferably from 0.1 mg/L to 100 mg/L, more preferably from 0.5 mg/L to 50 mg/L, most preferably from 1 mg/L to 30 mg/L.
  • an oxygen atom-containing high-molecular weight organic compound may be used as the plating inhibitor.
  • Specific examples thereof include polyethylene glycol, polypropylene glycol, a polyoxyethylene-polyoxypropylene random copolymer, and a polyoxyethylene-polyoxypropylene block copolymer. Of those, polyethylene glycol is preferred.
  • the molecular weight of such oxygen atom-containing high-molecular weight organic compound is preferably from 500 to 100,000, more preferably from 1,000 to 10,000.
  • polyethylene glycol having a molecular weight of from 1,000 to 10,000 is most preferred.
  • the concentration of the oxygen atom-containing high-molecular weight organic compound in the copper electroplating solution is preferably from 50 mg/L to 5,000 mg/L, more preferably from 100 mg/L to 3,000 mg/L.
  • a well-known solvent may be used as a solvent for the copper electroplating solution.
  • the solvent include: water; alcohols, such as methanol, ethanol, isopropyl alcohol, and n-butanol; acetic acid esters, such as ethyl acetate, butyl acetate, and methoxyethyl acetate; ethers, such as tetrahydrofuran, tetrahydropyran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, dibutyl ether, and dioxane; ketones, such as methyl butyl ketone, methyl isobutyl ketone, ethyl butyl ketone, dipropyl ketone, diisobutyl ketone, methyl amyl ketone, cyclohexanone, and methylcyclohexanone; and hydrocarbons, such as hexane,
  • solvents water and alcohols are preferred, and water is more preferred.
  • Any other additive known to be capable of being added to a plating solution may be optionally used in the copper electroplating solution of the present invention to the extent that the effect of the present invention is not inhibited.
  • Examples of the other additive include an anthraquinone derivative, a cationic surfactant, a nonionic surfactant, an anionic surfactant, an amphoteric surfactant, an alkanesulfonic acid, an alkanesulfonic acid salt, an alkanesulfonic acid ester, a hydroxyalkanesulfonic acid ester, and a hydroxyalkanesulfonic acid organic acid ester (provided that a compound corresponding to the component (B) of the present invention is excluded).
  • the concentration of such other additive in the copper electroplating solution is preferably from 0.1 mg/L to 500 mg/L, more preferably from 0.5 mg/L to 100 mg/L.
  • the pH of the copper electroplating solution is not particularly limited, but generally acidic conditions of pH 4 or less, preferably acidic conditions of pH 3 or less, and more preferably strong acidic conditions of pH 2 or less are adopted.
  • a pH meter LAQUA F-70 manufactured by HORIBA, Ltd. or the like may be used for the measurement of the pH.
  • a temperature at the time of the measurement of the pH may be about room temperature.
  • the copper electroplating method of the present invention may be performed in the same manner as a related-art copper electroplating method except that the copper electroplating solution of the present invention is used as a copper electroplating solution.
  • a copper electroplating method comprising forming a copper layer on a substrate to be plated is described.
  • a paddle stirring-type plating apparatus only needs to be used as a copper electroplating apparatus.
  • the plating tank of the copper electroplating apparatus is filled with the copper electroplating solution of the present invention, and the substrate to be plated is immersed in the copper electroplating solution.
  • a product obtained by forming a resist pattern on a Si substrate with a copper seed layer through use of a photoresist may be used as the substrate to be plated.
  • the temperature of the copper electroplating solution is from 10° C. to 70° C., preferably from 20° C. to 60° C., and a current density falls within the range of from 1 A/dm 2 to 70 A/dm 2 , preferably from 5 A/dm 2 to 50 A/dm 2 , more preferably from 15 A/dm 2 to 35 A/dm 2 .
  • air stirring, quick liquid current stirring, or mechanical stirring with a stirring blade or the like may be used as a method of stirring the copper electroplating solution.
  • a plated product to be manufactured by using the copper electroplating method of the present invention is not particularly limited, and examples thereof include a wide range of products, such as materials for automobile industry (such as a heat sink, a carburetor part, a fuel injector, a cylinder, various valves, and an inner part of an engine), materials for electronic industry (such as contact, a circuit, a semiconductor package, a printed board, a film resistor, a capacitor, a hard disk, a magnetic material, a lead frame, a nut, a magnet, a resistor, a stem, a computer part, an electronic part, a laser oscillation device, an optical memory device, an optical fiber, a filter, a thermistor, a heater, a heater for high temperature, a varistor, a magnetic head, various sensors (gas, temperature, humidity, light, speed, and the like), and MEMS), precision instruments (such as a copying machine part, an optical instrument part, and a timepiece part), aviation or ship materials (such
  • the copper electroplating method of the present invention is preferably used for the materials for electronic industry, in which a particularly fine pattern is required, is more preferably used in the manufacture of, among the materials, a semiconductor package and a printed board typified by TSV formation, bump formation, and the like, and is most preferably used in the semiconductor package.
  • Sulfuric acid, the component (B), copper sulfate pentahydrate, hydrochloric acid, SPS, PEG4000, and water were mixed so as to give compositions shown in Table 1 to obtain Example copper plating solutions 1 to 9.
  • the balance in each of the compositions of the copper plating solutions shown in Table 1 was water, and the concentration of each component was adjusted with water.
  • SPS manufactured by Tokyo Chemical Industry Co., Ltd.
  • PEG4000 manufactured by ADEKA Corporation
  • used in the Examples are disodium 3,3′-dithiobis(1-propanesulfonate) and polyethylene glycol having a weight-average molecular weight of from 3,600 to 4,400, respectively.
  • Example Hydrogen copper Component Component (B) Component chloride SPS PEG4000 plating bath (A) (g/L) (concentration) (C) (g/L) (mg/L) (mg/L) (mg/L) (mg/L)
  • Example 1 180 Compound 50 50 10 1,000 No. 7 (10 g/L)
  • Example 2 180 Compound 50 50 10 1,000 No. 7 (30 g/L)
  • Example 3 180 Compound 50 70 10 1,000 No. 7 (50 g/L)
  • Example 4 180 Compound 30 50 10 1,000 No. 7 (3 g/L)
  • Example 5 130 Compound 50 30 10 1,000 No. 7 (25 g/L)
  • Example 6 130 Compound 50 50 10 1,000 No. 7 (5 g/L)
  • Example 7 130 Compound 60 50 10 1,000 No. 7 (1.5 g/L)
  • Example 8 180 Compound 50 30 10 1,000 No. 8 (30 g/L)
  • Example 9 180 Compound 50 50 10 1,000 No. 2 (10 g/L)
  • Comparative copper plating solutions 1 to 8 Sulfuric acid, the component (B) or another component, copper sulfate pentahydrate, hydrochloric acid, SPS, PEG4000, and water were mixed so as to give compositions shown in Table 2 to obtain Comparative copper plating solutions 1 to 8.
  • the balance in each of the compositions of the copper plating solutions shown in Table 2 was water, and the concentration of each component was adjusted with water.
  • SPS and PEG4000 used in Comparative Examples are disodium 3,3′-dithiobis(1-propanesulfonate) and polyethylene glycol having a weight-average molecular weight of from 3,600 to 4,400, respectively.
  • Comparative compounds 1 to 5 used as the other components are compounds shown below.
  • a paddle stirring-type plating apparatus was used as a copper electroplating apparatus, and the plating tank of the paddle stirring-type plating apparatus was filled with each of the copper electroplating solutions of Examples 1 to 9 and Comparative Examples 1 to 8.
  • a substrate to be plated was immersed in each of the copper electroplating solutions.
  • a product obtained by forming a resist pattern (shape: having an opening portion of a circular sectional shape, opening diameter: 75 ⁇ m) on a Si substrate with a copper seed layer through use of a photoresist was used as the substrate to be plated.
  • copper of each copper electroplating solution was filled in the opening portion of the resist under the following plating conditions by a copper electroplating method.
  • a copper layer was formed on the substrate to be plated.
  • a minimum level 3 (L Min ) and a maximum level 4 (L Max ) of a copper layer 1 formed on the surface of a substrate 2 to be plated by each of Evaluation Examples 1 to 9 and Comparative Evaluation Examples 1 to 8 as illustrated in FIG. 1 were measured by observing a section of the copper layer 1 with a laser microscope (manufactured by Keyence Corporation, model number: VK-9700), and ⁇ L was calculated from the following equation. In addition, the content of organic residues in the obtained copper layer was measured by secondary ion mass spectrometry.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Electroplating And Plating Baths Therefor (AREA)
  • Electroplating Methods And Accessories (AREA)
US17/781,949 2019-12-04 2020-11-24 Copper electroplating solution, method of producing same, and copper electroplating method Abandoned US20230025950A1 (en)

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JP2019219370 2019-12-04
JP2019-219370 2019-12-04
PCT/JP2020/043577 WO2021111919A1 (ja) 2019-12-04 2020-11-24 電解銅めっき液、その製造方法及び電解銅めっき方法

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US6676823B1 (en) * 2002-03-18 2004-01-13 Taskem, Inc. High speed acid copper plating

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JPH07316875A (ja) * 1994-05-23 1995-12-05 C Uyemura & Co Ltd 電気銅めっき用添加剤及び電気銅めっき浴
EP1422320A1 (en) * 2002-11-21 2004-05-26 Shipley Company, L.L.C. Copper electroplating bath
JP4704761B2 (ja) 2005-01-19 2011-06-22 石原薬品株式会社 電気銅メッキ浴、並びに銅メッキ方法
JP4799887B2 (ja) 2005-03-24 2011-10-26 石原薬品株式会社 電気銅メッキ浴、並びに銅メッキ方法
JP4750486B2 (ja) * 2005-07-06 2011-08-17 株式会社Adeka 電解銅メッキ用添加剤、該添加剤を含有する電解銅メッキ浴及び該メッキ浴を使用する電解銅メッキ方法
JP2007016264A (ja) * 2005-07-06 2007-01-25 Adeka Corp 新規化合物、該化合物からなる電解銅メッキ用添加剤、該添加剤を含有する電解銅メッキ浴、該メッキ浴を使用する電解銅メッキ方法
JP5637671B2 (ja) * 2009-09-16 2014-12-10 上村工業株式会社 電気銅めっき浴及びその電気銅めっき浴を用いた電気めっき方法
CN105102687A (zh) * 2013-04-02 2015-11-25 株式会社Adeka 电镀铜浴用添加剂、含该添加剂的电镀铜浴及使用该电镀铜浴的电镀铜方法

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US6676823B1 (en) * 2002-03-18 2004-01-13 Taskem, Inc. High speed acid copper plating

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KR20220109405A (ko) 2022-08-04
TWI901613B (zh) 2025-10-21
CN114761621A (zh) 2022-07-15
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WO2021111919A1 (ja) 2021-06-10
TW202130860A (zh) 2021-08-16
JP7710376B2 (ja) 2025-07-18

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