WO2012133225A1 - Electro copper plating additive and electro copper plating bath - Google Patents
Electro copper plating additive and electro copper plating bath Download PDFInfo
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- WO2012133225A1 WO2012133225A1 PCT/JP2012/057594 JP2012057594W WO2012133225A1 WO 2012133225 A1 WO2012133225 A1 WO 2012133225A1 JP 2012057594 W JP2012057594 W JP 2012057594W WO 2012133225 A1 WO2012133225 A1 WO 2012133225A1
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- 0 *C(*)(C(*)(*)O*=C)NN Chemical compound *C(*)(C(*)(*)O*=C)NN 0.000 description 1
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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
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Abstract
Description
本出願は、日本国において2011年3月28日に出願された日本特許出願番号特願2011-070667を基礎として優先権を主張するものであり、これらの出願を参照することにより、本出願に援用される。 The present invention relates to an additive for electrolytic copper plating and an electrolytic copper plating bath, and more particularly to an additive for electrolytic copper plating suitable as a brightener for a copper sulfate plating bath and an electrolytic copper plating bath containing the additive.
This application claims priority on the basis of Japanese Patent Application No. 2011-070667 filed on Mar. 28, 2011 in Japan. By referring to these applications, the present application Incorporated.
H-(EO)a-(PO)m-(EO)b-H
で示される、ポリプロピレングリコールにエチレンオキサイドを付加したポリマーが使用されている。なお、上記式中において、EOはオキシエチレン基を表し、POはオキシプロピレン基を表し、n=a+bとする。 Further, as brighteners other than the above compounds, the following general formula H- (EO) a- (PO) m- (EO) b-H
A polymer obtained by adding ethylene oxide to polypropylene glycol is used. In the above formula, EO represents an oxyethylene group, PO represents an oxypropylene group, and n = a + b.
(ブロックポリマーの合成)
気密反応容器に、n-プロパノール600g(10モル)と水酸化カリウム5.6g(0.1モル)を採り、窒素ガス雰囲気下でプロピレンオキサイド870g(15モル)を90~130℃、2~5kg/cm2の加圧下で付加反応させた。プロピレンオキサイドの付加反応終了後、反応容器を冷却し、次にエチレンオキサイド660g(15モル)を加えて、同様の条件で付加反応させた。 <Example 1>
(Synthesis of block polymer)
In an airtight reaction vessel, 600 g (10 mol) of n-propanol and 5.6 g (0.1 mol) of potassium hydroxide are taken, and 870 g (15 mol) of propylene oxide is added at 90 to 130 ° C. and 2 to 5 kg in a nitrogen gas atmosphere. The addition reaction was carried out under a pressure of / cm 2 . After completion of the addition reaction of propylene oxide, the reaction vessel was cooled, and then 660 g (15 mol) of ethylene oxide was added to carry out the addition reaction under the same conditions.
下記組成
硫酸銅(Cu2SO4・5H2O) 200g/L
濃硫酸 50g/L
NaCl 115mg/L
からなる硫酸銅めっき液に、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及び上述のようにして合成したポリオキシエチレン(15)ポリオキシプロピレン(15)プロピルエーテル0.2g/Lを加えためっき浴を用い、総電流2A、時間10分でハルセル試験器を用いてめっき処理を行った。なお、pH<1、温度25℃、陰極電流密度0.15~4A/dm2のめっき処理条件とした。 (Plating treatment and plating film evaluation)
Following composition Copper sulfate (Cu 2 SO 4 · 5H 2 O) 200g / L
Concentrated sulfuric acid 50g / L
NaCl 115mg / L
A copper sulfate plating solution comprising bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diethylsafranine diazotized product 50 mg / L, and polyoxy synthesized as described above Using a plating bath to which 0.2 g / L of ethylene (15) polyoxypropylene (15) propyl ether was added, plating treatment was performed using a Hull Cell tester at a total current of 2 A and time of 10 minutes. The plating conditions were pH <1, temperature 25 ° C., cathode current density 0.15 to 4 A / dm 2 .
(ブロックポリマーの合成)
気密反応容器に、アリルアルコール(2-プロペン-1-オール)580g(10モル)と水酸化カリウム5.6g(0.1モル)を採り、窒素ガス雰囲気下でプロピレンオキサイド870g(15モル)を90~130℃、2~5kg/cm2の加圧下で付加反応させた。プロピレンオキサイドの付加反応終了後、反応容器を冷却し、次にエチレンオキサイド660g(15モル)を加えて、同様の条件で付加反応させた。 <Example 2>
(Synthesis of block polymer)
In an airtight reaction vessel, 580 g (10 mol) of allyl alcohol (2-propen-1-ol) and 5.6 g (0.1 mol) of potassium hydroxide are taken, and 870 g (15 mol) of propylene oxide is added in a nitrogen gas atmosphere. The addition reaction was performed at 90 to 130 ° C. under a pressure of 2 to 5 kg / cm 2 . After completion of the addition reaction of propylene oxide, the reaction vessel was cooled, and then 660 g (15 mol) of ethylene oxide was added to carry out the addition reaction under the same conditions.
実施例2では、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及び上述のようにして合成したポリオキシエチレン(15)ポリオキシプロピレン(15)アリルエーテル0.2g/Lを加えた硫酸銅めっき浴を用いたこと以外は、実施例1と同様にしてハルセル試験器を用いてめっき処理を行った。 (Plating treatment and plating film evaluation)
In Example 2, as additives, bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diazotized product of diethyl safranin 50 mg / L, and polyoxyethylene (15 ) Plating was performed using a Hull cell tester in the same manner as in Example 1 except that a copper sulfate plating bath to which 0.2 g / L of polyoxypropylene (15) allyl ether was added was used.
(ブロックポリマーの合成)
気密反応容器に、n-ブタノール740g(10モル)と水酸化カリウム5.6g(0.1モル)を採り、窒素ガス雰囲気下でプロピレンオキサイド580g(10モル)を90~130℃、2~5kg/cm2の加圧下で付加反応させた。プロピレンオキサイドの付加反応終了後、反応容器を冷却し、次にエチレンオキサイド660g(15モル)を加えて、同様の条件で付加反応させた。 <Example 3>
(Synthesis of block polymer)
In an airtight reaction vessel, 740 g (10 mol) of n-butanol and 5.6 g (0.1 mol) of potassium hydroxide are taken, and 580 g (10 mol) of propylene oxide is added at 90 to 130 ° C. and 2 to 5 kg in a nitrogen gas atmosphere. The addition reaction was carried out under a pressure of / cm 2 . After completion of the addition reaction of propylene oxide, the reaction vessel was cooled, and then 660 g (15 mol) of ethylene oxide was added to carry out the addition reaction under the same conditions.
実施例3では、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及び上述のようにして合成した、ポリオキシエチレン(15)ポリオキシプロピレン(10)ブチルエーテル0.2g/Lを加えた硫酸銅めっき浴を用いたこと以外は、実施例1と同様にしてハルセル試験器を用いてめっき処理を行った。 (Plating treatment and plating film evaluation)
In Example 3, as additives, bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diazotized product of diethyl safranin 50 mg / L, and polyoxyethylene ( 15) Plating was performed using a Hull cell tester in the same manner as in Example 1 except that a copper sulfate plating bath to which 0.2 g / L of polyoxypropylene (10) butyl ether was added was used.
(ブロックポリマーの合成)
気密反応容器に、n-ヘキサノール1020g(10モル)と水酸化カリウム5.6g(0.1モル)を採り、窒素ガス雰囲気下でプロピレンオキサイド290g(5モル)を90~130℃、2~5kg/cm2の加圧下で付加反応させた。プロピレンオキサイドの付加反応終了後、反応容器を冷却し、次にエチレンオキサイド880g(20モル)を加えて、同様の条件で付加反応させた。 <Example 4>
(Synthesis of block polymer)
In an airtight reaction vessel, 1020 g (10 mol) of n-hexanol and 5.6 g (0.1 mol) of potassium hydroxide are taken, and 290 g (5 mol) of propylene oxide is 90 to 130 ° C. and 2 to 5 kg in a nitrogen gas atmosphere. The addition reaction was carried out under a pressure of / cm 2 . After completion of the addition reaction of propylene oxide, the reaction vessel was cooled, and then 880 g (20 mol) of ethylene oxide was added to cause addition reaction under the same conditions.
実施例4では、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及び上述のようにして合成した、ポリオキシエチレン(20)ポリオキシプロピレン(5)ヘキシルエーテル0.2g/Lを加えた硫酸銅めっき浴を用いたこと以外は、実施例1と同様にしてハルセル試験器を用いてめっき処理を行った。 (Plating treatment and plating film evaluation)
In Example 4, as additives, bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diazotized product of diethyl safranin 50 mg / L, and polyoxyethylene (as described above) ( 20) Plating was performed using a Hull cell tester in the same manner as in Example 1 except that a copper sulfate plating bath added with 0.2 g / L of polyoxypropylene (5) hexyl ether was used.
(ブロックポリマーの合成)
気密反応容器に、2-エチルヘキサノール1300g(10モル)と水酸化カリウム5.6g(0.1モル)を採り、窒素ガス雰囲気下でプロピレンオキサイド174g(3モル)を90~130℃、2~5kg/cm2の加圧下で付加反応させた。プロピレンオキサイドの付加反応終了後、反応容器を冷却し、次にエチレンオキサイド1100g(25モル)を加えて、同様の条件で付加反応させた。 <Example 5>
(Synthesis of block polymer)
In an airtight reaction vessel, 1300 g (10 mol) of 2-ethylhexanol and 5.6 g (0.1 mol) of potassium hydroxide are taken, and 174 g (3 mol) of propylene oxide is added at 90 to 130 ° C. under a nitrogen gas atmosphere. The addition reaction was carried out under a pressure of 5 kg / cm 2 . After completion of the addition reaction of propylene oxide, the reaction vessel was cooled, and then 1100 g (25 mol) of ethylene oxide was added to cause addition reaction under the same conditions.
実施例5では、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及び上述のようにして合成した、ポリオキシエチレン(25)ポリオキシプロピレン(3)2-エチルヘキシルエーテル0.2g/Lを加えた硫酸銅めっき浴を用いたこと以外は、実施例1と同様にしてハルセル試験器を用いてめっき処理を行った。 (Plating treatment and plating film evaluation)
In Example 5, as additives, bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diazotized product of diethyl safranin 50 mg / L, and polyoxyethylene (as described above) ( 25) Plating was performed using a Hull cell tester in the same manner as in Example 1 except that a copper sulfate plating bath to which 0.2 g / L of polyoxypropylene (3) 2-ethylhexyl ether was added was used.
(ブロックポリマーの合成)
気密反応容器に、1-ドデカノール1860g(10モル)と水酸化カリウム5.6g(0.1モル)を採り、窒素ガス雰囲気下でプロピレンオキサイド116g(2モル)を90~130℃、2~5kg/cm2の加圧下で付加反応させた。プロピレンオキサイドの付加反応終了後、反応容器を冷却し、次にエチレンオキサイド1320g(30モル)を加えて、同様の条件で付加反応させた。 <Example 6>
(Synthesis of block polymer)
In an airtight reaction vessel, 1860 g (10 mol) of 1-dodecanol and 5.6 g (0.1 mol) of potassium hydroxide are taken, and 116 g (2 mol) of propylene oxide is added at 90 to 130 ° C. and 2 to 5 kg in a nitrogen gas atmosphere. The addition reaction was carried out under a pressure of / cm 2 . After completion of the addition reaction of propylene oxide, the reaction vessel was cooled, and then 1320 g (30 mol) of ethylene oxide was added to carry out the addition reaction under the same conditions.
実施例6では、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及び上述のようにして合成した、ポリオキシエチレン(30)ポリオキシプロピレン(2)ドデシルエーテル0.2g/Lを加えた硫酸銅めっき浴を用いたこと以外は、実施例1と同様にしてハルセル試験器を用いてめっき処理を行った。 (Plating treatment and plating film evaluation)
In Example 6, as additives, bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diazotized product of diethyl safranine 50 mg / L, and polyoxyethylene ( 30) Plating was performed using a Hull cell tester in the same manner as in Example 1 except that a copper sulfate plating bath to which 0.2 g / L of polyoxypropylene (2) dodecyl ether was added was used.
(めっき処理及びめっき被膜評価)
比較例1では、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及びポリエチレングリコール0.2g/Lを加えた硫酸銅めっき浴を用いたこと以外は、実施例1と同様にしてハルセル試験器を用いてめっき処理を行い、析出形成されためっき被膜の評価を行った。なお、この比較例1並びに下記比較例2及び3においても、銅めっき浴には空気を吹き込んで十分に攪拌を行った。 <Comparative Example 1>
(Plating treatment and plating film evaluation)
In Comparative Example 1, copper sulfate to which bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diazotized product of diethyl safranin 50 mg / L, and polyethylene glycol 0.2 g / L were added as additives. Except for using a plating bath, the plating treatment was performed using a Hull cell tester in the same manner as in Example 1 to evaluate the deposited plating film. In Comparative Example 1 and Comparative Examples 2 and 3 below, air was blown into the copper plating bath and sufficiently stirred.
(めっき処理及びめっき被膜評価)
比較例2では、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及びポリプロピレングリコール0.2g/Lを加えた硫酸銅めっき浴を用いたこと以外は、実施例1と同様にしてハルセル試験器を用いてめっき処理を行い、析出形成されためっき被膜の評価を行った。 <Comparative Example 2>
(Plating treatment and plating film evaluation)
In Comparative Example 2, copper sulfate to which bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diazotized product of diethyl safranin 50 mg / L, and polypropylene glycol 0.2 g / L were added as additives. Except that a plating bath was used, the plating treatment was performed using a Hull cell tester in the same manner as in Example 1 to evaluate the deposited plating film.
(めっき処理及びめっき被膜評価)
比較例3では、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及び、ポリプロピレングリコールにエチレンオキサイドを付加して得られたブロックポリマー(H-(EO)a-(PO)m-(EO)b-H、m=17、n=a+b=9)0.2g/Lを加えた硫酸銅めっき浴を用いたこと以外は、実施例1と同様にしてハルセル試験器を用いてめっき処理を行い、析出形成されためっき被膜の評価を行った。 <Comparative Example 3>
(Plating treatment and plating film evaluation)
In Comparative Example 3, the additive was obtained by adding ethylene oxide to bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diazotized product of diethyl safranin 50 mg / L, and polypropylene glycol. Other than using a copper sulfate plating bath to which 0.2 g / L of a block polymer (H- (EO) a- (PO) m- (EO) b-H, m = 17, n = a + b = 9) was added In the same manner as in Example 1, plating treatment was performed using a Hull cell tester, and the deposited plating film was evaluated.
(めっき処理及びめっき被膜評価)
比較例4では、添加剤として、ビス-(ω-スルホプロピル)-ジスルフィド2ナトリウム塩10mg/L、ジエチルサフラニンのジアゾ化処理物50mg/L、及び、n-ブタノールにエチレンオキサイドとプロピレンオキサイドとを同時に付加して得られたランダムポリマー0.2g/Lを加えた硫酸銅めっき浴を用いたこと以外は、実施例1と同様にしてハルセル試験器を用いてめっき処理を行い、析出形成されためっき被膜の評価を行った。 <Comparative example 4>
(Plating treatment and plating film evaluation)
In Comparative Example 4, bis- (ω-sulfopropyl) -disulfide disodium salt 10 mg / L, diethylsafranine diazotized product 50 mg / L, and ethylene oxide and propylene oxide in n-butanol were used as additives. Except for using a copper sulfate plating bath to which 0.2 g / L of a random polymer obtained by addition at the same time was used, plating was performed using a Hull cell tester in the same manner as in Example 1 to form a precipitate. The plating film was evaluated.
Claims (3)
- 下記一般式(1)で示されるブロックポリマー化合物からなる電気銅めっき用添加剤。
- 上記ブロックポリマー化合物は、不活性ガス雰囲気下、炭素数1~15のアルキルアルコール又はアルケニルアルコールにプロピレンオキサイドを付加反応させた後、エチレンオキサイドを加えて付加反応させて得られることを特徴とする請求項1記載の電気銅めっき用添加剤。 The block polymer compound is obtained by subjecting an addition reaction of propylene oxide to an alkyl alcohol or alkenyl alcohol having 1 to 15 carbon atoms in an inert gas atmosphere, followed by addition reaction of ethylene oxide. Item 4. The additive for electrolytic copper plating according to Item 1.
- 上記請求項1記載の電気銅めっき用添加剤を含有した電気銅めっき浴。 An electrolytic copper plating bath containing the additive for electrolytic copper plating according to claim 1.
Priority Applications (3)
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CN201280015856.5A CN103443334B (en) | 2011-03-28 | 2012-03-23 | Cathode copper plates application additive and electrolysis electroless copper bath |
KR1020137026205A KR101940593B1 (en) | 2011-03-28 | 2012-03-23 | Electro copper plating additive and electro copper plating bath |
US14/004,011 US20130341199A1 (en) | 2011-03-28 | 2012-03-23 | Electro copper plating additive and electro copper plating bath |
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JP2011070667A JP5363523B2 (en) | 2011-03-28 | 2011-03-28 | Additive for electrolytic copper plating and electrolytic copper plating bath |
JP2011-070667 | 2011-03-28 |
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US (1) | US20130341199A1 (en) |
JP (1) | JP5363523B2 (en) |
KR (1) | KR101940593B1 (en) |
CN (1) | CN103443334B (en) |
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JP6733314B2 (en) * | 2015-09-29 | 2020-07-29 | 三菱マテリアル株式会社 | High-purity copper electrolytic refining additive and high-purity copper manufacturing method |
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 |
CN113166962A (en) | 2018-11-07 | 2021-07-23 | 科文特亚股份有限公司 | Satin copper bath and method for depositing a satin copper layer |
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- 2012-03-23 US US14/004,011 patent/US20130341199A1/en not_active Abandoned
- 2012-03-23 KR KR1020137026205A patent/KR101940593B1/en active IP Right Grant
- 2012-03-23 WO PCT/JP2012/057594 patent/WO2012133225A1/en active Application Filing
- 2012-03-23 CN CN201280015856.5A patent/CN103443334B/en active Active
- 2012-03-27 TW TW101110579A patent/TWI608130B/en active
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JP2009526128A (en) * | 2006-02-02 | 2009-07-16 | エントン インコーポレイテッド | Electrodeposition of copper in microelectronics. |
WO2010069810A1 (en) * | 2008-12-19 | 2010-06-24 | Basf Se | Composition for metal electroplating comprising leveling agent |
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WO2015077772A1 (en) * | 2013-11-25 | 2015-05-28 | Enthone Inc. | Electrodeposition of copper |
CN105917032A (en) * | 2013-11-25 | 2016-08-31 | 乐思股份有限公司 | Electrodeposition of copper |
Also Published As
Publication number | Publication date |
---|---|
TWI608130B (en) | 2017-12-11 |
US20130341199A1 (en) | 2013-12-26 |
CN103443334A (en) | 2013-12-11 |
TW201300581A (en) | 2013-01-01 |
JP5363523B2 (en) | 2013-12-11 |
CN103443334B (en) | 2018-02-06 |
KR20140013021A (en) | 2014-02-04 |
KR101940593B1 (en) | 2019-01-21 |
JP2012201976A (en) | 2012-10-22 |
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