Acidic bath for electrolytically depositing a copper deposit containing halogenated or pseudohalogenated monomeric phenazinium compounds

An onium compound and halide technology, applied in the field of halogenated or pseudo-halogenated monomeric phenazinium compounds, can solve the problems of product quality change, time-consuming reaction, high cost, long reaction time, moderate stability and the like

Inactive Publication Date: 2006-12-20
ATOTECH DEUT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] A disadvantage of the described method is that a separate reaction vessel is required for each synthetic step including dye dissolution
Due to the long reaction time and the moderate stability of diazonium compounds which are prone to decomposition in acidic media, uncontrolled reactions may occur resulting in changes in the quality of the desired product
Furthermore, this type of time-consuming reaction is very expensive from an economic point of view

Method used

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  • Acidic bath for electrolytically depositing a copper deposit containing halogenated or pseudohalogenated monomeric phenazinium compounds
  • Acidic bath for electrolytically depositing a copper deposit containing halogenated or pseudohalogenated monomeric phenazinium compounds
  • Acidic bath for electrolytically depositing a copper deposit containing halogenated or pseudohalogenated monomeric phenazinium compounds

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preparation example Construction

[0056] A novel preparation method was used to synthesize halogenated or pseudohalogenated monomeric phenazinium compounds. In conventional methods, in the first synthetic step, the diazonium compound is formed by diazotizing a monomeric phenazinium compound in a first synthetic vessel in the presence of a mineral acid and a diazotizing agent, followed by a second synthetic step , and only after transferring the diazo compound to a second synthesis vessel, react the diazo compound in the presence of a mineral acid and a halogenated or pseudohalogenated cuprous(I) halide to form the halogenated or pseudohalogenated monomeric phen Azinium compounds, compared to conventional methods, the method according to the invention involves first and second reaction steps, both of which are carried out in the presence of monomeric phenazinium compounds, mineral acids, diazotizing agents and halides or pseudohalides in a single container (one-pot method).

[0057] Thus, the one-pot method is...

preparation Embodiment 1

[0085] Preparative Example 1: No additional halide added

[0086] 3-Chloro-7-N,N-dimethylamino-2-methyl-5-phenyl-phenazinium chloride

[0087] Suspend 1 g of 3-amino-7-N,N-dimethylamino-2-methyl-5-phenyl-phenazinium chloride in 15 ml of 35% by weight hydrochloric acid and heat it to 50 °C . Next, saturated aqueous sodium nitrite solution (454 mg in 6 ml of water) was slowly added dropwise, and then stirred at this temperature for one hour. The reaction formulation was cooled to room temperature, and the resulting dark blue solid material was filtered off and dried. Yield 615 mg (58.5% of theory).

[0088] After quantitative analysis by mass spectrometry, the purity of the obtained material was found to be 94 mole %, ie only 6 mole % of the material used was not composed of the monomeric compound.

preparation Embodiment 2

[0089] Preparative Example 2: Addition of Additional Halide

[0090] 3-Chloro-7-N,N-dimethylamino-2-methyl-5-phenyl-phenazinium chloride

[0091] Suspend 1 g of 3-amino-7-N,N-dimethylamino-2-methyl-5-phenyl-phenazinium chloride in 15 ml of 35% by weight hydrochloric acid and heat it to 50 °C . Next, 347 mg of nickel(II) chloride was added, and a saturated aqueous sodium nitrite solution (454 mg in 6 ml of water) was slowly added dropwise, followed by stirring at this temperature for one hour. The reaction formulation was cooled to room temperature, and the resulting dark blue solid material was filtered off and dried. Yield 724 mg (69.0% of theory).

[0092] After quantitative analysis by mass spectrometry, it was found that the purity of the obtained material was 90 mol%, ie only 10 mol% of the used material was not composed of the monomeric compound.

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Abstract

For manufacturing particularly uniform and mirror bright copper coatings that are leveled and ductile as well using a relatively high current density, halogenated or pseudohalogenated monomeric pheanzinium compounds or a purity at least 85 mole-% and having the general chemical formula (I) are utilized in which R<1>, R<2>, R<3>, R<4>. R<5>, R<6>, R<7>, R<7''>, R<8>, R<9>, X and A<-> have the significations denoted in the claims. The compounds are prepared by diazotizing a suited starting compound prior to halogenating or pseudohalogenating it in the presence of mineral acid, diazotization means and halide or pseudohalide, with the reaction steps being run in one single vessel.

Description

technical field [0001] The present invention relates to halogenated or pseudohalogenated monomeric phenazinium compounds, processes for their preparation, acid baths containing said compounds for electrodepositing copper deposits, and methods of electrodepositing copper deposits using said acid baths. The halogenated or pseudo-halogenated monomeric phenazinium compounds are useful as additives in copper electroplating baths to more specifically form mirror-bright, planar copper deposits to create decorative surfaces. Furthermore, the compounds are useful as additives in copper electroplating baths to selectively and completely fill blind microchannels in printed circuit boards and trenches and vias on semiconductor wafers with copper. The compound can also be used as an additive in a copper electroplating bath for depositing copper on the surface of a semiconductor substrate with grooves during the manufacture of an integrated circuit, so that the entire surface of the semicon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/46C25D3/38
CPCC07D241/46C25D3/38
Inventor 海科·布伦纳沃尔夫冈·达姆斯乌多·格里泽(已故)
Owner ATOTECH DEUT GMBH
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