US20110220512A1 - Plating bath and method - Google Patents

Plating bath and method Download PDF

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Publication number
US20110220512A1
US20110220512A1 US12/661,301 US66130110A US2011220512A1 US 20110220512 A1 US20110220512 A1 US 20110220512A1 US 66130110 A US66130110 A US 66130110A US 2011220512 A1 US2011220512 A1 US 2011220512A1
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US
United States
Prior art keywords
copper
alkyl
aryl
compounds
reaction product
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.)
Abandoned
Application number
US12/661,301
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English (en)
Inventor
Zukhra I. Niazimbetova
Elie H. Najjar
Maria Anna Rzeznik
Erik Reddington
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.)
Rohm and Haas Electronic Materials LLC
Original Assignee
Rohm and Haas Electronic Materials LLC
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 Rohm and Haas Electronic Materials LLC filed Critical Rohm and Haas Electronic Materials LLC
Priority to US12/661,301 priority Critical patent/US20110220512A1/en
Assigned to ROHM AND HAAS ELECTRONIC MATERIALS LLC reassignment ROHM AND HAAS ELECTRONIC MATERIALS LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NAJJAR, ELIE H., NIAZIMBETOVA, ZUKHRA I., REDDINGTON, ERIK, RZEZNIK, MARIA ANNA
Priority to JP2011055905A priority patent/JP6054594B2/ja
Priority to EP11158231A priority patent/EP2366692B1/fr
Priority to CN2011101158165A priority patent/CN102250319A/zh
Priority to CN201210395534.XA priority patent/CN102888629B/zh
Priority to KR1020110022943A priority patent/KR101739410B1/ko
Priority to TW100108653A priority patent/TWI428326B/zh
Priority to US13/207,658 priority patent/US8268158B2/en
Publication of US20110220512A1 publication Critical patent/US20110220512A1/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms

Definitions

  • leveling agents used in copper plating baths provide better leveling of the deposit across the substrate surface but tend to worsen the throwing power of the electroplating bath. Throwing power is defined as the ratio of the hole center copper deposit thickness to its thickness at the surface.
  • Newer PCBs are being manufactured that contain both through-holes and blind vias. Current bath additives, in particular current leveling agents, do not provide level copper deposits on the substrate surface and fill through-holes and/or fill blind vias effectively.
  • the present invention provides a reaction product of one or more imidazole compounds with one or more epoxide-containing compounds; wherein at least one imidazole compound has the formula
  • the present invention also provides a copper electroplating bath including: a source of copper ions, an electrolyte, and a leveling agent, wherein the leveling agent is a reaction product of one or more imidazole compounds with one or more epoxide-containing compounds; wherein at least one imidazole compound has the formula
  • feature refers to the geometries on a substrate.
  • aperture refers to recessed features including through-holes and blind vias.
  • plat refers to metal electroplating.
  • Deposition and “plating” are used interchangeably throughout this specification.
  • Halide refers to fluoride, chloride, bromide and iodide.
  • halo refers to fluoro, chloro, bromo and iodo.
  • alkyl includes linear, branched and cyclic alkyl.
  • Accelelerator refers to an organic additive that increases the plating rate of the electroplating bath.
  • Preferred acids include sulfuric acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, and mixtures thereof.
  • the acids are typically present in an amount in the range of from 1 to 300 g/L, preferably from 5 to 250 g/L, and more preferably from 10 to 225 g/L.
  • Electrolytes are generally commercially available from a variety of sources and may be used without further purification.
  • R 1 , R 2 and R 3 are independently chosen from H, (C 1- C 12 )alkyl, (C 2 -C 12 )alkenyl, and aryl and provided that R 1 and R 2 are not both H. That is, the reaction products contain at least one imidazole wherein at least one of R 1 and R 2 is (C 1 -C 12 )alkyl, (C 2 -C 12 )alkenyl, or aryl. Such imidazole compound is substituted with a (C 1- C 12 )alkyl, (C 2 -C 12 )alkenyl, or aryl at the 4- and/or 5-position.
  • Y ⁇ H and X ⁇ Cl or Br and more preferably, X ⁇ Cl.
  • the percent cracking was determined according to the industry standard procedure, IPC-TM-650-2.6.8. Thermal Stress, Plated-Through Holes, published by IPC (Northbrook, Ill., USA), dated May, 2004, revision E. The lower the percentage of cracking, the better the plating bath performed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Electroplating And Plating Baths Therefor (AREA)
  • Electroplating Methods And Accessories (AREA)
  • Chemically Coating (AREA)
US12/661,301 2010-03-15 2010-03-15 Plating bath and method Abandoned US20110220512A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US12/661,301 US20110220512A1 (en) 2010-03-15 2010-03-15 Plating bath and method
JP2011055905A JP6054594B2 (ja) 2010-03-15 2011-03-14 めっき浴および方法
EP11158231A EP2366692B1 (fr) 2010-03-15 2011-03-15 Bain et méthode de placage électrolytique au cuivre
CN2011101158165A CN102250319A (zh) 2010-03-15 2011-03-15 电镀液及电镀方法
CN201210395534.XA CN102888629B (zh) 2010-03-15 2011-03-15 电镀液及电镀方法
KR1020110022943A KR101739410B1 (ko) 2010-03-15 2011-03-15 도금조 및 방법
TW100108653A TWI428326B (zh) 2010-03-15 2011-03-15 鍍覆浴及方法
US13/207,658 US8268158B2 (en) 2010-03-15 2011-08-11 Plating bath and method

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12/661,301 US20110220512A1 (en) 2010-03-15 2010-03-15 Plating bath and method

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/207,658 Division US8268158B2 (en) 2010-03-15 2011-08-11 Plating bath and method

Publications (1)

Publication Number Publication Date
US20110220512A1 true US20110220512A1 (en) 2011-09-15

Family

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Family Applications (2)

Application Number Title Priority Date Filing Date
US12/661,301 Abandoned US20110220512A1 (en) 2010-03-15 2010-03-15 Plating bath and method
US13/207,658 Active US8268158B2 (en) 2010-03-15 2011-08-11 Plating bath and method

Family Applications After (1)

Application Number Title Priority Date Filing Date
US13/207,658 Active US8268158B2 (en) 2010-03-15 2011-08-11 Plating bath and method

Country Status (6)

Country Link
US (2) US20110220512A1 (fr)
EP (1) EP2366692B1 (fr)
JP (1) JP6054594B2 (fr)
KR (1) KR101739410B1 (fr)
CN (2) CN102888629B (fr)
TW (1) TWI428326B (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110220513A1 (en) * 2010-03-15 2011-09-15 Rohm And Haas Electronic Materials Llc Plating bath and method
US20110220514A1 (en) * 2010-03-15 2011-09-15 Rohm And Haas Electronic Materials Llc Plating bath and method
EP2586893A2 (fr) 2011-10-24 2013-05-01 Rohm and Haas Electronic Materials LLC Appareil et bain de placage de cuivre
US9562299B2 (en) 2013-01-16 2017-02-07 Samsung Electronics Co., Ltd. Copper electroplating solution and copper electroplating apparatus
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
US10405422B2 (en) * 2012-07-09 2019-09-03 Shikoku Chemicals Corporation Copper film-forming agent and method for forming copper film
US10718059B2 (en) 2017-07-10 2020-07-21 Rohm And Haas Electronic Materials Llc Nickel electroplating compositions with cationic polymers and methods of electroplating nickel
CN114381769A (zh) * 2021-12-24 2022-04-22 广州市慧科高新材料科技有限公司 一种超速填孔镀铜整平剂的合成方法以及应用

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US20140238868A1 (en) 2013-02-25 2014-08-28 Dow Global Technologies Llc Electroplating bath
US9598787B2 (en) * 2013-03-14 2017-03-21 Rohm And Haas Electronic Materials Llc Method of filling through-holes
US20140262801A1 (en) * 2013-03-14 2014-09-18 Rohm And Haas Electronic Materials Llc Method of filling through-holes
US9403762B2 (en) * 2013-11-21 2016-08-02 Rohm And Haas Electronic Materials Llc Reaction products of guanidine compounds or salts thereof, polyepoxides and polyhalogens
US9273407B2 (en) 2014-03-17 2016-03-01 Hong Kong Applied Science and Technology Research Institute Company Limited Additive for electrodeposition
CN104005061B (zh) * 2014-06-05 2016-05-18 中节能太阳能科技有限公司 一种用于太阳能电池前电极电镀铜的负整平剂
US9809891B2 (en) 2014-06-30 2017-11-07 Rohm And Haas Electronic Materials Llc Plating method
US10154598B2 (en) * 2014-10-13 2018-12-11 Rohm And Haas Electronic Materials Llc Filling through-holes
US9725816B2 (en) 2014-12-30 2017-08-08 Rohm And Haas Electronic Materials Llc Amino sulfonic acid based polymers for copper electroplating
US9783905B2 (en) 2014-12-30 2017-10-10 Rohm and Haas Electronic Mateirals LLC Reaction products of amino acids and epoxies
US9611560B2 (en) 2014-12-30 2017-04-04 Rohm And Haas Electronic Materials Llc Sulfonamide based polymers for copper electroplating
CN105002527B (zh) * 2015-07-31 2017-06-16 广东光华科技股份有限公司 整平剂溶液及其制备方法和应用
EP3135709B1 (fr) * 2015-08-31 2018-01-10 ATOTECH Deutschland GmbH Polymères d'urée imidazoyle et leur utilisation dans des compositions de bains de placage de métaux ou d'alliages de métaux
US10988852B2 (en) 2015-10-27 2021-04-27 Rohm And Haas Electronic Materials Llc Method of electroplating copper into a via on a substrate from an acid copper electroplating bath
US10508357B2 (en) 2016-02-15 2019-12-17 Rohm And Haas Electronic Materials Llc Method of filling through-holes to reduce voids and other defects
US10512174B2 (en) 2016-02-15 2019-12-17 Rohm And Haas Electronic Materials Llc Method of filling through-holes to reduce voids and other defects
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
CN117385426A (zh) * 2016-09-22 2024-01-12 麦克德米德乐思公司 在微电子件中的铜的电沉积
CN107236976B (zh) * 2017-07-25 2018-11-16 上海新阳半导体材料股份有限公司 整平剂、含其的金属电镀组合物及制备方法、应用
CN107217283B (zh) * 2017-07-25 2018-11-16 上海新阳半导体材料股份有限公司 整平剂、含其的金属电镀组合物、制备方法及应用
CN111892706A (zh) * 2020-07-23 2020-11-06 中国科学院大学温州研究院(温州生物材料与工程研究所) 一种peg偶联杂环化合物及其在酸性光亮镀铜中的应用
JPWO2022172823A1 (fr) 2021-02-15 2022-08-18
KR102339867B1 (ko) * 2021-07-30 2021-12-16 와이엠티 주식회사 레벨링제 및 이를 포함하는 비아홀 충진을 위한 전기도금 조성물
KR102339868B1 (ko) * 2021-07-30 2021-12-16 와이엠티 주식회사 레벨링제 및 이를 포함하는 비아홀 충진을 위한 전기도금 조성물
CN115894908A (zh) * 2021-09-30 2023-04-04 华为技术有限公司 聚合物、整平剂及其制备方法、电镀液和电镀方法
US20230279577A1 (en) 2022-03-04 2023-09-07 Rohm And Haas Electronic Materials Llc Method of filling through-holes to reduce voids

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110220513A1 (en) * 2010-03-15 2011-09-15 Rohm And Haas Electronic Materials Llc Plating bath and method
US20110220514A1 (en) * 2010-03-15 2011-09-15 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
US8268157B2 (en) 2010-03-15 2012-09-18 Rohm And Haas Electronic Materials Llc Plating bath and method
EP2586893A2 (fr) 2011-10-24 2013-05-01 Rohm and Haas Electronic Materials LLC Appareil et bain de placage de cuivre
US8454815B2 (en) 2011-10-24 2013-06-04 Rohm And Haas Electronics Materials Llc Plating bath and method
US10405422B2 (en) * 2012-07-09 2019-09-03 Shikoku Chemicals Corporation Copper film-forming agent and method for forming copper film
US9562299B2 (en) 2013-01-16 2017-02-07 Samsung Electronics Co., Ltd. Copper electroplating solution and copper electroplating apparatus
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
US10718059B2 (en) 2017-07-10 2020-07-21 Rohm And Haas Electronic Materials Llc Nickel electroplating compositions with cationic polymers and methods of electroplating nickel
CN114381769A (zh) * 2021-12-24 2022-04-22 广州市慧科高新材料科技有限公司 一种超速填孔镀铜整平剂的合成方法以及应用

Also Published As

Publication number Publication date
KR101739410B1 (ko) 2017-05-24
US8268158B2 (en) 2012-09-18
CN102888629A (zh) 2013-01-23
TWI428326B (zh) 2014-03-01
TW201139382A (en) 2011-11-16
CN102888629B (zh) 2014-12-31
EP2366692A2 (fr) 2011-09-21
EP2366692B1 (fr) 2013-02-20
US20110290660A1 (en) 2011-12-01
JP2011190260A (ja) 2011-09-29
KR20110103891A (ko) 2011-09-21
EP2366692A3 (fr) 2011-11-02
CN102250319A (zh) 2011-11-23
JP6054594B2 (ja) 2016-12-27

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