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Heterocyclic diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds and preparation method and applications thereof

A technology of diketopyrrolopyrrole and quaternary ammonium salts, which is applied in the field of heterocyclic diketopyrrolopyrrole quaternary ammonium salts and its preparation, can solve the problems of insufficient positioning in low potential areas and slow light output rate, and achieve Effects of suppressing copper deposition, increasing cathodic polarization, and good plating performance

Active Publication Date: 2019-05-31
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, the weakness of this system is that the light output rate is slow, and the low potential area is insufficient.

Method used

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  • Heterocyclic diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds and preparation method and applications thereof
  • Heterocyclic diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds and preparation method and applications thereof
  • Heterocyclic diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063]

[0064] 3,6-bis(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (preparation method: add 4g metal sodium particles to a 100mL In a three-necked flask of tert-amyl alcohol, add 20 mg of ferric chloride to tert-amyl alcohol, react in an oil bath at 110°C for 2 hours, cool down to 60°C, add 7.5g of 2-cyanothiophene, start to heat up to 105°C, and drop 7.2mL of diisopropyl succinate, dripped for three hours, reacted at 105°C for 4 hours, cooled to room temperature, added acetic acid to make it neutral, filtered to obtain a solid, washed three times with methanol, and deionized Washed with water three times and dried to obtain 3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione.) (3g, 10mmol) , 1,6-dibromohexane (9.76g, 40mmol), potassium tert-butoxide (4.49g, 40mmol) and the solvent acetonitrile 30mL were mixed in a 150mL pressure bottle, heated and stirred under reflux for 8 hours, and the After suction filtration, the obtained filtrate was rota...

Embodiment 2

[0070] The effect of the compound B-1 prepared in Example 1 on the current density of copper ion deposition was tested.

[0071] Preparation 1 contains 117.5g / L CuSO 4 ·5H 2 O, 180g / L H 2 SO 4, 50mg / L chloride ion copper sulfate solution, with the Pt rotating electrode as the working electrode, the platinum rod as the counter electrode and the Ag / AgCl as the reference electrode, and the rotation speed is 2000 rpm. Add different concentrations (concentrations are 0, 2, 4, 6, 8, 10 μmol / l, respectively, compound B-1 is dissolved in deionized water) solution of compound B-1 prepared in Example 1, and make a cathodic polarization curve. test. like figure 1 shown, figure 1 is the polarization curve of the electrolyte containing different concentrations of compound B-1, the scanning speed is 2mVs -1 . The inhibitory effect of compound B-1 prepared according to Example 1 on the deposition of copper ions on the surface of copper materials at different concentrations and the po...

Embodiment 3

[0080] The performance of compound B-1 prepared in Example 1 for inhibiting the deposition of copper ions was tested.

[0081] Formula one contains 117.5g / L CuSO 4 ·5H 2 O, 180g / L H 2 SO 4 , 50mg / L chloride ion copper sulfate solution, with the Pt rotating electrode as the working electrode, the platinum rod as the counter electrode and the Ag / AgCl as the reference electrode, and the rotation speed is 2000 rpm. Add different concentrations (concentrations are respectively 0, 2, 4, 6, 8, 10 μmol / l, compound B-1 is dissolved in deionized water) compound B-1 solution prepared in Example 1 into the solution respectively, do cyclic voltammetry Curve test. like image 3 shown, image 3 are the cyclic voltammetry curves of the effect of compound B-1 at different concentrations on copper deposition, the inhibitory effect of compound B-1 prepared according to Example 1 on the deposition of copper ions on the surface of copper materials at different concentrations and the cyclic v...

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Abstract

The invention discloses heterocyclic diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds. The structural formula of the compounds is represented by a formula B, and the definitions of all substituents are shown in the description. The provided heterocyclic diketopyrrolopyrrole (DPP) quaternary ammonium salt compounds have a good electroplating performance and can be used as a quaternaryammonium salt leveling agent for acidic copper plating.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a heterocyclic diketopyrrolopyrrole quaternary ammonium salt compound and a preparation method and application thereof. 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, the manufacture of many products in the a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C25D3/38
CPCC07D487/04C25D3/38
Inventor 王利民王康王峰王桂峰李俊何玉龙王小敏玛丽亚田禾陈立荣韩建伟黄卓
Owner EAST CHINA UNIV OF SCI & TECH
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