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Quinacridone quaternary ammonium salt compound and preparation method and application thereof

A technology of quaternary ammonium salts and quinacridones, which is applied in the field of quinacridone quaternary ammonium salts and their preparation, and can solve problems such as insoluble quinacridone, high temperature, and difficult purification of quinacridone , to achieve the effect of inhibiting copper deposition, increasing cathode polarization, and simple preparation method

Active Publication Date: 2019-08-09
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In all known crystal phases, there are strong intermolecular hydrogen bonds between quinacridone molecules, which makes it difficult for unsubstituted quinacridones to dissolve in various solvents, and vacuum sublimation is also difficult. High temperature is required, so the purification of quinacridone is very difficult, which limits its application in many fields

Method used

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  • Quinacridone quaternary ammonium salt compound and preparation method and application thereof
  • Quinacridone quaternary ammonium salt compound and preparation method and application thereof
  • Quinacridone quaternary ammonium salt compound and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0055]

[0056] 2,9-Dimethyl-quinolino[2,3-b]-acridine-5,12-dihydro-7,14-dione (3.40g, 10mmol), 1,6-dibromohexyl Alkanes (12.20g, 50mmol), sodium hydride (1.20g, 50mmol) and 50mL solvent tetrahydrofuran were mixed together in a 150mL pressure bottle, heated and stirred under reflux for 24h, and the solid was removed by suction filtration with a suction filter bottle, and the obtained filtrate was rotary evaporated The solvent was removed, and the crude product was obtained and subjected to silica gel column chromatography, dichloromethane:petroleum ether=1:1 as developing solvent, to obtain solid compound A-14.33g, yield 65%.

[0057]

[0058] 2,9-dimethyl-5,12-bis(6-bromohexyl)-quinolino[2,3-b]-acridine-5,12-dihydro-7,14-dione is A-1 (3.33g, 5mmol), trimethylamine hydrochloride (2.39g, 25mmol), sodium bicarbonate (2.10g, 25mmol) and 30mL of acetonitrile solvent were mixed together in a 120mL reaction flask, heated and stirred under reflux for 12h, After the reaction so...

Embodiment 2

[0062] The effect of compound B-1 on the current density of copper ion deposition was tested.

[0063] Preparation one containing 60g / L CuSO 4 ·5H 2 O, 200g / L H 2 SO 4 , 50mg / L chloride ion copper sulfate solution, with Pt rotating electrode as working electrode, platinum rod as counter electrode and Ag / AgCl as reference electrode, under the situation that rotating speed is 2000 revolutions, in the above-mentioned copper sulfate solution containing chloride ion Add different concentrations (concentrations are 0, 2, 4, 6, 8, 10 μmol / L respectively, compound B-1 is dissolved in deionized water) the compound B-1 solution prepared in Example 1, and make cathodic polarization curve test. Such as figure 1 as shown, figure 1 It is the polarization curve of the electrolyte containing different concentrations of compound B-1, and the scanning speed is 2mVs -1 . Compound B-1 prepared according to Example 1 is at different concentrations, on the copper material surface to the inh...

Embodiment 3

[0066] The ability of compound B-1 to inhibit the deposition of copper ions was tested.

[0067] Preparation one containing 60g / L CuSO 4 ·5H 2 O, 200g / L H 2 SO 4 , 50mg / L chloride ion copper sulfate solution, with Pt rotating electrode as working electrode, platinum rod as counter electrode and Ag / AgCl as reference sink electrode, under the situation that rotating speed is 2000 revolutions, in above-mentioned copper sulfate solution containing chloride ion Add different concentrations (0, 2, 4, 6, 8, 10 μmol / L respectively, compound B-1 is dissolved in deionized water) of the compound B-1 solution prepared in Example 1 to the solution for cyclic voltammetry Curve test. Such as image 3 as shown, image 3It is the cyclic voltammetry curve of the influence of different concentrations of compound B-1 on copper deposition, the compound B-1 prepared according to Example 1 is at different concentrations, the inhibitory effect on copper ion deposition on the surface of copper m...

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Abstract

The invention discloses a quinacridone quaternary ammonium salt compound. A structural formula is shown as a general formula B, and the definition of each substituent is detailed in the description. The quinacridone quaternary ammonium salt compound has good electroplating performance and can produce a synergistic inhibition effect with other electroplating additives, and the electroplating performance of the quinacridone quaternary ammonium salt compound is verified through a cyclic voltammetry curve, a polarization curve and a continuous current timing addition curve.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a quinacridone quaternary ammonium salt compound and its preparation method and application. Background technique [0002] A printed circuit board (Printed-Circuit-Board, PCB) is an essential part of an electronic product and a motherboard that carries electronic components in an electronic product. At present, electronic products are rapidly developing in the direction of miniaturization, convenience, and intelligence. Multilayer printed circuit boards (HDI-PCBs) with high connectivity density are one of the important components for manufacturing these electronic products. Metallized vias or blind vias are used in multilayer circuit boards to achieve conduction between different layers. Through-hole copper plating is an important way to achieve through-hole metallization, and it is also a very important technology in the multilayer PCB manufacturing proce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C25D3/38
CPCC07D471/04C25D3/38
Inventor 王利民王小敏王康李俊魏小川韩建伟田禾赵敏
Owner EAST CHINA UNIV OF SCI & TECH
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