WO2023166552A1 - スルホニオ基含有エーテル化合物を含むめっき液 - Google Patents

スルホニオ基含有エーテル化合物を含むめっき液 Download PDF

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Publication number
WO2023166552A1
WO2023166552A1 PCT/JP2022/008580 JP2022008580W WO2023166552A1 WO 2023166552 A1 WO2023166552 A1 WO 2023166552A1 JP 2022008580 W JP2022008580 W JP 2022008580W WO 2023166552 A1 WO2023166552 A1 WO 2023166552A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
plating solution
ether compound
plating
acid
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.)
Ceased
Application number
PCT/JP2022/008580
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
一喜 岸本
翔太 樋口
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JCU Corp
Original Assignee
JCU Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by JCU Corp filed Critical JCU Corp
Priority to EP22929700.7A priority Critical patent/EP4488421A4/en
Priority to KR1020247031812A priority patent/KR20240155294A/ko
Priority to JP2022541302A priority patent/JP7162162B1/ja
Priority to PCT/JP2022/008580 priority patent/WO2023166552A1/ja
Priority to US18/842,532 priority patent/US20250179676A1/en
Priority to CN202280092757.0A priority patent/CN118922586A/zh
Priority to TW111145030A priority patent/TWI835422B/zh
Publication of WO2023166552A1 publication Critical patent/WO2023166552A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • 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 reactive group on the ether compound is not particularly limited, and a desired group can be selected from various reactive groups such as an epoxy group, a sulfonyl group, a sulfonyloxy group, a carboxy group, and an amino group.
  • an ether compound having an allyl group and an allyl group-containing sulfonium compound can be combined with a peroxide or the like to prepare a sulfonio group-containing ether compound.
  • the reactive group is preferably an epoxy group or a sulfonyloxy group, and particularly preferably an epoxy group, from the viewpoint that the reaction proceeds reliably and rapidly.
  • R 1 and R 2 are the same as R 1 and R 2 in Formula 1 above;
  • A is a substituted or unsubstituted aliphatic or aromatic divalent hydrocarbon group;
  • Eo and Er is a group containing an ether moiety ;
  • the compounds represented by Formulas 1 ⁇ 1 and 1 ⁇ 2 are sulfonio group-containing ether compounds represented by Formula 1, wherein E is a substituted or unsubstituted aliphatic or aromatic hydrocarbon group to which an ether moiety is bonded. corresponds to
  • the sulfonio group-containing ether compound can also be prepared from any organic sulfur compound having substituents R 1 and R 2 , but the organic It is preferred to use sulfur compounds and/or organic sulfur compounds of the formula 2 ⁇ .
  • R 1 and R 2 are also preferably C 1-6 hydrocarbon groups, especially C 1-3 alkyl groups. In particular, both R 1 and R 2 are preferably methyl groups.
  • One particularly preferred embodiment of the organic sulfur compound represented by formula 2 ⁇ is the compound represented by formula 2-1 below. Of course, other organic sulfur compounds can also be preferably used.
  • the counter anion of the organic sulfonium compound represented by formula 2 ⁇ is not particularly limited, and includes alkylsulfonate anions such as methylsulfonate anion, boric acid anions such as tetrafluoroborate anion, hexafluorophosphate anion, etc. Any type of anion such as a phosphate anion, a sulfate anion, a nitrate anion, and a halide ion may be used.
  • amphoteric surfactants include betaine, carboxybetaine, imidazolinium betaine, sulfobetaine, aminocarboxylic acids, and the like.
  • SE-7 sulfonio group-containing ether compound
  • the total volume was adjusted to 40 mL with water to obtain a sulfonio group-containing ether compound (SE-11) as an aqueous solution with a concentration of 105 g/L.
  • SE-11 a sulfonio group-containing ether compound
  • the formation of a sulfonio group after the reaction was confirmed by 1 H-NMR.
  • the weight average molecular weight of SE-11 was 7,460.

Landscapes

  • 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)
PCT/JP2022/008580 2022-03-01 2022-03-01 スルホニオ基含有エーテル化合物を含むめっき液 Ceased WO2023166552A1 (ja)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP22929700.7A EP4488421A4 (en) 2022-03-01 2022-03-01 VENEER SOLUTION CONTAINING AN ETHER COMPOUND CONTAINING A SULFONIO GROUP
KR1020247031812A KR20240155294A (ko) 2022-03-01 2022-03-01 설포니오기 함유 에테르 화합물을 포함하는 도금액
JP2022541302A JP7162162B1 (ja) 2022-03-01 2022-03-01 スルホニオ基含有エーテル化合物を含むめっき液
PCT/JP2022/008580 WO2023166552A1 (ja) 2022-03-01 2022-03-01 スルホニオ基含有エーテル化合物を含むめっき液
US18/842,532 US20250179676A1 (en) 2022-03-01 2022-03-01 Plating solution containing sulfonio group-containing ether compound
CN202280092757.0A CN118922586A (zh) 2022-03-01 2022-03-01 包含含锍基的醚化合物的镀液
TW111145030A TWI835422B (zh) 2022-03-01 2022-11-24 包含含有鋶基之醚化合物之鍍敷液

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2022/008580 WO2023166552A1 (ja) 2022-03-01 2022-03-01 スルホニオ基含有エーテル化合物を含むめっき液

Publications (1)

Publication Number Publication Date
WO2023166552A1 true WO2023166552A1 (ja) 2023-09-07

Family

ID=83804246

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2022/008580 Ceased WO2023166552A1 (ja) 2022-03-01 2022-03-01 スルホニオ基含有エーテル化合物を含むめっき液

Country Status (7)

Country Link
US (1) US20250179676A1 (https=)
EP (1) EP4488421A4 (https=)
JP (1) JP7162162B1 (https=)
KR (1) KR20240155294A (https=)
CN (1) CN118922586A (https=)
TW (1) TWI835422B (https=)
WO (1) WO2023166552A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119352117A (zh) * 2024-12-23 2025-01-24 西安智同航空科技有限公司 一种航空紧固件表面镀银的方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3000799A (en) * 1960-02-10 1961-09-19 Harshaw Chem Corp Nickel plating solutions
JP2003105584A (ja) 2001-07-26 2003-04-09 Electroplating Eng Of Japan Co 微細配線埋め込み用銅メッキ液及びそれを用いた銅メッキ方法
JP2008231033A (ja) * 2007-03-20 2008-10-02 Kanto Denka Kogyo Co Ltd Ｓ−ｎ結合を含むスルホニウムカチオンを有するイオン液体およびその製造方法
WO2011135716A1 (ja) 2010-04-30 2011-11-03 荏原ユージライト株式会社 新規化合物およびその利用
JP2016183410A (ja) 2015-03-26 2016-10-20 三菱マテリアル株式会社 スルホニウム塩を用いためっき液

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4388450A (en) * 1981-03-13 1983-06-14 General Electric Company Aromatic polyvinyl ethers and heat curable molding compositions obtained therefrom
US6676823B1 (en) * 2002-03-18 2004-01-13 Taskem, Inc. High speed acid copper plating
US20050070701A1 (en) * 2003-09-29 2005-03-31 Hochstetler Spencer Erich Detection of living cells in polymers or pigments
US7887693B2 (en) * 2007-06-22 2011-02-15 Maria Nikolova Acid copper electroplating bath composition
KR20140010398A (ko) * 2011-02-23 2014-01-24 바스프 에스이 술포늄 술페이트, 그의 제조법 및 용도

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3000799A (en) * 1960-02-10 1961-09-19 Harshaw Chem Corp Nickel plating solutions
JP2003105584A (ja) 2001-07-26 2003-04-09 Electroplating Eng Of Japan Co 微細配線埋め込み用銅メッキ液及びそれを用いた銅メッキ方法
JP2008231033A (ja) * 2007-03-20 2008-10-02 Kanto Denka Kogyo Co Ltd Ｓ−ｎ結合を含むスルホニウムカチオンを有するイオン液体およびその製造方法
WO2011135716A1 (ja) 2010-04-30 2011-11-03 荏原ユージライト株式会社 新規化合物およびその利用
JP2016183410A (ja) 2015-03-26 2016-10-20 三菱マテリアル株式会社 スルホニウム塩を用いためっき液

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP4488421A4

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119352117A (zh) * 2024-12-23 2025-01-24 西安智同航空科技有限公司 一种航空紧固件表面镀银的方法

Also Published As

Publication number Publication date
TWI835422B (zh) 2024-03-11
EP4488421A1 (en) 2025-01-08
CN118922586A (zh) 2024-11-08
JP7162162B1 (ja) 2022-10-27
EP4488421A4 (en) 2026-02-25
US20250179676A1 (en) 2025-06-05
JPWO2023166552A1 (https=) 2023-09-07
TW202336287A (zh) 2023-09-16
KR20240155294A (ko) 2024-10-28

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