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Diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds, and preparation and application thereof

A technology of diketopyrrolopyrrole and quaternary ammonium salt compound, which is applied in the application field of acidic copper sulfate electroplating, and can solve problems such as fogging of the plating layer and increased environmental protection pressure caused by dyes

Active Publication Date: 2015-06-24
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these additives are usually required to be used at a lower temperature when used, and when the temperature is high, it is easy to cause fogging of the coating and other phenomena.
In addition, from the perspective of environmental protection, dyes will increase the pressure on environmental protection in sewage treatment.

Method used

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  • Diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds, and preparation and application thereof
  • Diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds, and preparation and application thereof
  • Diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds, and preparation and application thereof

Examples

Experimental program
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Embodiment 1

[0047]

[0048] Take phthalimide (1.47g, 10mmol), 1,6-dibromohexane (7.26g, 30mmol) and potassium carbonate (2.94g, 40mmol) and place them in a reaction flask with acetonitrile as a solvent and mix them. Heat and stir at reflux, react for 12 hours, and filter with a suction filter bottle. The obtained filtrate is dried with anhydrous sodium sulfate, and the solvent is removed by rotary evaporation to obtain a crude product, which is recrystallized with ethanol to obtain 2.46 g of a solid, with a yield of 81%.

[0049] 1 H NMR (400MHz, CDCl 3 ): δ7.85(m, 2H), 7.72(m, 2H), 3.69(t, J 1 =8.0HZ,J 2 =8.0HZ, 2H), 3.40(t, J 1 =8.0HZ,J 2 =8.0HZ, 2H), 1.86(m, 2H), 1.70(m, 2H), 1.49(m, 2H), 1.37(m, 2H); 13 C NMR (CDCl 3 , 400MHz) δ168.42, 133.87, 132.10, 123.17, 37.81, 33.70, 32.58, 28.40, 27.69, 26.00; HRMS (TOF-ESI+): m / z: calcd for C 14 h 17 BrNO 2 + : 310.0437; Found: 310.0425;

[0050]

[0051] Take N-(6-bromohexyl)phthalimide (1.54g, 5mmol) and hydrazine hydrate (1...

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Abstract

The invention provides diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds, which are disclosed as the structural formula in the specification, wherein N-R2 is disclosed in the specification, and R1 is Cl, Br, F, I, CF3, CN, tBu, CH3, H, 2,6-F2, NH2, NO2, OH, CHO, COOH, 3,4-Cl2, or 3-F-5-CH3; n is a whole number ranging from 1 to 18; and x is Br, F, Cl, I, HSO3, HSO4, HCO3, CF3CO3, H2PO4, OTf, OTs or BF4. The compounds have stable structure, and can not cause the phenomena of coating fogging and the like at higher temperature; the big conjugate pi bond in the compounds can be adsorbed on the copper layer surface more easily, and the N center can inhibit the deposition of copper ions more efficiently; and thus, the compounds can be used for leveling as an electroplating leveling additive.

Description

technical field [0001] The present invention relates to a series of DPP quaternary ammonium salt compounds and a preparation method thereof, as well as their application as an electroplating leveling agent in electroplating, more particularly in acid copper sulfate electroplating. Background technique [0002] In the 21st century, with the development of electronic technology, the electroplated copper layer has been widely used in the field of electronic information products because of its good electrical conductivity, thermal conductivity and mechanical ductility. In the field of manufacturing, such as from printed circuit board (PCB) manufacturing to IC packaging, to electronic fields such as copper interconnect technology for large-scale integrated circuits (chips), copper electroplating technology has become an indispensable key electroplating in modern microelectronics manufacturing. one of the technologies. In addition, in the field of general hardware electroplating,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09B57/00C25D3/38
Inventor 王利民宋龙锋陈飚余建军吴生英王峰王桂峰田禾王振炎陈立荣黄卓
Owner EAST CHINA UNIV OF SCI & TECH
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