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Polymers containing benzimidazole moieties as levelers

一种聚合物、化合物的技术，应用在有机化学、印刷电路制造、印刷电路等方向，能够解决损害电镀浴均镀能力等问题

Active Publication Date: 2016-06-22
ROHM & HAAS ELECTRONICS MATERIALS LLC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In general, levelers used in copper plating baths provide better leveling of deposits across the substrate surface, but tend to compromise the throwing ability of the plating bath

Method used

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  • Polymers containing benzimidazole moieties as levelers
  • Polymers containing benzimidazole moieties as levelers
  • Polymers containing benzimidazole moieties as levelers

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0090] Example 1 (comparison)

[0091] Imidazole (6.8 g, 100 mmol) and sodium hydride (2.64 g, 11 mmol) were dissolved in 50 mL of anhydrous tetrahydrofuran. The mixture was stirred and cooled in an ice bath for 2 hours until hydrogen evolution ceased. 1,4-Dibromobutane (10.8 g, 50 mmol) was added and the mixture was stirred at room temperature for 12 hours. After removing the precipitate, the solvent was removed to obtain 1,4-bis(N-imidazolyl)butane. By 1HNMR (Bruker (Bruker), 400MHz, H 2 O-d2) Analysis of 1,4-bis(N-imidazolyl)butane showed the following peaks, confirming the structure: δppm: 8.81 (s, 2H, Haram); 7.51 (m, 4H, Haram.); 4.21 (m, 4H, 2xCH 2 -N), 4.257(m, 4H, 2xCH 2 -NH) and 1.87-1.90 (m, 4H, 2xCH 2 -CH 2 -NH).

[0092] 1,4-Bis(N-imidazolyl)butane (2.18g, 10mmol) and 1,4-dibromobutane (2.16g, 10mmol) were dissolved in dimethylformamide and the mixture was heated at 100°C 24 hours. The resulting precipitate (Product A) was collected by filtration and was...

example 2

[0094] Benzimidazole (11.8 g, 100 mmol) and sodium hydride (2.64 g, 11 mmol) were dissolved in 50 mL of anhydrous tetrahydrofuran. The mixture was stirred and cooled in an ice bath for 2 hours until hydrogen evolution ceased. 1,4-Dibromobutane (10.8 g, 50 mmol) was added and the mixture was stirred at room temperature for 12 hours. After removing the precipitate, the solvent was removed by evaporation to obtain 1,4-bis(N-benzimidazolyl)butane. By 1HNMR (Bruker (Bruker), 400MHz, H 2 O-d2) Analysis of 1,4-bis(N-imidazolyl)butane showed the following peaks, confirming the structure: δppm: 8.07 (s, 2H, Haram); 7.625 (m, 2H, Harom.); 7.447 (m, 2H, Harom), 7.238(m, 4H, Harom) 4.89(m, 4H, 2xCH 2 -N), 4.25(m, 4H, 2xCH 2 -NH) and 1.87(m, 4H, 2xCH 2 -CH 2 -NH).

[0095] 1,4-bis(N-benzimidazolyl)butane (1.16g, 4mmol), 1,4-bis(N-imidazolyl)butane (1.14g, 6mmol) and 1,4-dibromobutane The alkane was dissolved in dimethylformamide and the mixture was heated at 100 °C for 24 hours. T...

example 3

[0097] Benzimidazole (4.72 g, 4 mmol), imidazole (4.08 g, 6 mmol) and sodium hydride (2.64 g, 11 mmol) were dissolved in 50 mL of anhydrous tetrahydrofuran. The mixture was stirred and cooled in an ice bath for 2 hours until hydrogen evolution ceased. 1,4-Dibromobutane (10.8 g, 50 mmol) was added and the mixture was stirred at room temperature for 12 hours. After removing the precipitate by filtration, 50 ml of dimethylformamide and 10.8 g of 1,4-dibromobutane (50 mmol) were added. The mixture was heated at 100°C for 24 hours. The resulting precipitate (product 2) was collected by filtration and washed with ethyl acetate. According to the NMR results, the molar ratio of benzimidazolium to imidazolium in the product was 1.27. Mn was found to be 3,407 and Mw was found to be 12,581.

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Abstract

Polymers of reaction products of dihalogens and compounds containing benzimidazole moieties are included in metal electroplating compositions to provide level metal deposits on substrates.

Description

technical field [0001] The present invention is directed to polymers containing benzimidazole moieties as levelers in electroplating compositions. More specifically, the present invention is directed to polymers containing benzimidazole moieties as levelers for electroplating compositions with good thermal reliability and throwing ability. Background technique [0002] Methods of electroplating articles with metallic paint generally involve passing an electric current between two electrodes in a plating solution, one of which is the article to be plated. A typical acidic copper plating solution contains dissolved copper (usually copper sulfate), an acid electrolyte (such as sulfuric acid) in an amount sufficient to render the bath conductive, and special additives to improve plating uniformity and metal deposit quality. Such additives include accelerators, levelers and inhibitors, among others. [0003] Electrolytic copper plating solutions are used in a variety of industr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/20C07D235/08C25D3/00
CPCC25D3/02C25D3/32C25D3/38H05K3/241C25D7/123C25D7/00C08G73/0677C25D5/56H05K3/423
Inventor L·段Y·李T·孙S·冯C·陈Z·I·尼亚齐姆贝托瓦M·A·瑞兹尼克
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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