CN111454195B - Isoindigo quaternary ammonium salt compound and preparation method and application thereof - Google Patents
Isoindigo quaternary ammonium salt compound and preparation method and application thereof Download PDFInfo
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/38—Electroplating: Baths therefor from solutions of copper
Abstract
The invention discloses an isoindigo quaternary ammonium salt compound, the structural formula is shown as a general formula B:
the definition of each substituent is shown in the specification. The isoindigo quaternary ammonium compound has good electroplating performance and can be used as a quaternary ammonium leveling agent for acid copper electroplating.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to an isoindigo quaternary ammonium salt compound, and a preparation method and application thereof.
Background
With the development of industries such as 5G, unmanned driving, internet of things and the like, the market has higher and higher requirements for electronic information products, and a Printed-Circuit-Board (PCB) is an essential component of an electronic product and is a motherboard for carrying electronic elements in the electronic product. At present, electronic products are rapidly developed toward miniaturization, convenience and intellectualization, and a multilayer printed circuit board (HDI-PCB) having a high connection density is one of important parts for manufacturing the electronic products. Metallized through holes or blind holes are used in multilayer circuit boards to achieve conduction between different layers. Through hole copper electroplating is an important way for realizing through hole metallization, and is also a very important technology in the manufacturing process of the multilayer PCB. However, in the direct current plating process, it is difficult to obtain a uniform thickness of a plated layer in a via hole using a conventional plating solution due to non-uniform distribution of current density in the via hole, and the use of an organic additive is an effective and economical method. Therefore, it is highly desirable to develop effective, stable, and highly adaptable additives for through-hole plating.
The method for preparing the printed circuit board is mainly an acid sulfate copper plating method, and compared with cyanide alkaline copper plating, cyanide-free alkaline copper plating and the like, an acid sulfate copper plating system has the advantages of high efficiency, safety, stability and the like, so that the system is generally selected in a through hole metallization electroplating process. In acid sulfate copper plating, uniform plating in holes can hardly be obtained only by a base plating solution, so that additives are required to be added, and the additives have extremely important function in uniform plating of through holes.
Through many years of research, the main electroplating additive system at present comprises three types, namely an inhibitor, an accelerator and a leveling agent. The inhibitor mainly acts to inhibit the deposition of copper ions on the surface of the copper plate, the accelerator mainly acts to promote the deposition of copper ions in the holes of the copper plate, and the leveling agent mainly acts to promote the deposition of copper ions on the positions, protruding out of the copper plate, of the copper ions, but the capability of inhibiting the deposition of copper ions on the concave positions is weak, so that the difference of the inhibition capability is generated, and the difference leads the difference between the convex positions and the concave positions to be smaller and smaller until the surface of the copper plate is flat. Inhibitors and accelerators have matured over the past, and therefore much research is now being put into the development and mechanistic study of leveling agents.
The addition of a leveler makes it easier to control the effective concentration of the entire additive system. Thus, many scholars believe that levelers play a very critical, and sometimes even decisive, role throughout the via plating additive system. Development of different types of levelers has become a focus of research. From some reports to date, it has been found that leveling agents are usually quaternary ammonium compounds or nitrogen-containing heterocyclic compounds, typically dyes. The leveling agent is a high-strength inhibitor, and can achieve the leveling purpose under the matching use of other additives.
Copper electrodeposition is widely used in Printed Circuit Boards (PCBs), integrated Circuit (IC) packages, and sophisticated microprocessors. This is because copper has good electrical conductivity, thermal conductivity and corrosion resistance, and acidic copper plating is the most important method in copper electrodeposition. The process has the following characteristics: the components of the electroplating solution are simple copper sulfate and sulfuric acid, the electroplating solution has high current efficiency and high deposition speed, the whitening effect of the whitening agent is obvious, and the mirror-surface gloss coating can be obtained. In order to obtain coatings with good appearance, acceptable leveling properties and excellent physical properties, various organic additives must be added to the electroplating solution including suppressors, brightening and leveling agents.
Isoindigo is an isomer of natural organic pigment, namely, indigo, and in 2012, john r. Reynolds et al have application as a receptor in Electrochemical Supercapacitors (ESCs) because the molecule is a highly electron-deficient molecule. The application of the prepared super capacitor, changduk Yang et al in 2014, is based on the planarity and high polarity characteristics of the isoindigo derivative PTIIG-Np, and the isoindigo derivative PTIIG-Np is used in an organic crystal field diode. In 2017, florian Auras et al successfully apply isoindigo to covalent organic Compounds (COFs) by utilizing the characteristics of rigidity and planarity of isoindigo.
Disclosure of Invention
The first purpose of the invention is to provide a isoindigo quaternary ammonium salt compound.
The second purpose of the invention is to provide a preparation method of the isoindigo quaternary ammonium salt compound.
The third purpose of the invention is to provide the application of the isoindigo quaternary ammonium salt compound as a plating additive.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the first aspect of the present invention provides an isoindigo quaternary ammonium salt compound, the structural formula of which is shown as formula B:
wherein:
R 1 is phenyl, -Cl, -Br, -F, -I- t Bu、-CH 3 、-C 2 H 5 、-H、-CH 2 Cl、-OCH 3 、-NH 2 、-OH；
R 2 Is composed of
n is an integer of 1 to 18;
y is Br, F, cl, I, HSO 3 、HSO 4 、HCO 3 、CF 3 CO 3 、H 2 PO 4 OTf, OTs or BF 4 ；
Wherein when R is 2 Is composed of
When no Y is present.
Preferred compounds of the invention are: the structural formula of the isoindigo quaternary ammonium salt compound is shown as a general formula B:
R 2 is composed of
n is an integer of 1 to 18;
y is Br, F, cl, I, HSO 3 、HSO 4 、HCO 3 、CF 3 CO 3 、H 2 PO 4 OTf, OTs or BF 4 ；
Wherein when R is 2 Is composed of
When no Y is present.
More preferred compounds of the invention are: in formula B:
R 2 is composed of
n is 2, 3, 4, 5, 6 or 8;
y is Cl, br, F, I.
Preferred compounds of the invention are: in the general formula B, the compound represented by the formula,
R 2 is composed of
n is 2, 4, 6;
y is Cl, br, F, I.
The most preferred compounds of the invention are:
the second aspect of the present invention provides a preparation method of the isoindigo quaternary ammonium salt compound, including the following steps:
R 2 is composed of
n is an integer of 1 to 18; r 1 Is phenyl, -Cl, -Br, -F, -I- t Bu、-CH 3 、-C 2 H 5 、-H、-CH 2 Cl、-OCH 3 、-NH 2 、-OH；
Y is Cl, br, F, I;
x is Cl, br, F, I;
mixing substituted or unsubstituted isoindigo, alkyl halide and alkali with a proper solvent according to a molar ratio of 1 (2-10) to (2-10), reacting for 1-24 h, performing suction filtration, performing rotary evaporation on filtrate to remove the solvent to obtain a crude product, and performing column chromatography to obtain a compound A;
mixing the compound A, trimethylamine hydrochloride and sodium bicarbonate with the molar ratio of 1 (2-12) to (2-12) with a proper solvent, heating, stirring, refluxing and reacting for 1-24 h, cooling, filtering, removing the solvent from the filtrate by rotary evaporation, and carrying out column chromatography to obtain the isoindigo quaternary ammonium salt compound, namely the compound B.
The substituted or unsubstituted isoindigo is isoindigo.
The alkyl halides are 1, 8-dibromooctane, 1, 6-dibromohexane and 1, 4-dibromobutane.
The alkali is potassium hydroxide or sodium hydroxide.
The solvent is at least one of tetrahydrofuran, dimethyl sulfoxide and acetonitrile.
The molar ratio of the substituted or unsubstituted isoindigo, the alkyl halide and the base is 1.
The molar ratio of the compound A to trimethylamine hydrochloride to sodium bicarbonate is 1.
The third aspect of the invention provides an application of the isoindigo quaternary ammonium salt compound as a plating additive.
The electroplating additive is an electroplating leveling agent.
The electroplating is copper electroplating.
Due to the adoption of the technical scheme, the invention has the following advantages and beneficial effects:
the isoindigo quaternary ammonium salt compound has good electroplating performance, the quaternary ammonium salt structure can have larger coverage area on the surface of an electrode through nitrogen positive ions in the structure, namely quaternization centers, can increase cathode polarization, inhibit copper deposition so as to enable electroplating particles to be finer, enable a copper-plated layer to obtain high preferred crystal face orientation, and enable the copper-plated layer to be used as a quaternary ammonium salt leveling agent for acid copper electroplating.
The isoindigo quaternary ammonium salt compound has good electroplating performance and can generate synergistic inhibition effect with other electroplating additives, and the electroplating performance is verified by cyclic voltammetry curve, polarization curve and curve addition in constant current meter.
The isoindigo quaternary ammonium compound has simple preparation method and good electroplating performance, can be used as a quaternary ammonium leveling agent for acid copper electroplating, and obtains good effect through a series of tests.
Drawings
FIG. 1 is a schematic view of the polarization curve of an electrolyte containing different concentrations of compound B-1, with a scanning speed of 2mVs -1 。
FIG. 2 shows 2. Mu. Mol-The polarization curves of time-l bond NaGreen B (commercial product, JGB for short) and compound B-1 are compared and shown schematically, and the scanning speed is 2mVs -1 。
FIG. 3 is a graph showing the effect of different concentrations of compound B-1 on copper deposition.
FIG. 4 is a graph showing a comparison of cyclic voltammograms of Compound B-1 with JGB at 2. Mu. Mol/l.
FIG. 5 shows the current density at 2A/dm for different rotation speeds 2 Schematic diagram of galvanostatic addition curve of compound B-1.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
Isoindigo (manufacturer: future reagent, specification: 100g, purity: analytical purity), 1, 4-dibromobutane, 1, 6-dibromohexane, 1, 8-dibromooctane (manufacturer: shanghai Arlatin Biochemical technology Co., ltd., specification: 1kg, purity: 97.0%), trimethylamine hydrochloride (manufacturer: shanghai Mecang Biochemical technology Co., ltd., specification: 1000g, purity: 99%), sodium bicarbonate (manufacturer: shanghai Merlin Biochemical technology Co., ltd., specification: 500g, purity: 99%), tetrahydrofuran (manufacturer: bailingwei Tech Biochemical technology Co., ltd., specification: 500mL, purity: 99%), acetonitrile (manufacturer: bailingwei Biochemical technology Co., ltd., specification: 2.5L, purity: 99%), potassium hydroxide (manufacturer: shanghai Arlatin Biochemical technology Co., ltd., specification: 250g, purity: 60%).
Example 1
Isoindigo (0.26g, 1mmol) and potassium hydroxide (0.23g, 4mmol) were dissolved in 10mL of dimethyl sulfoxide, and the resulting solution was placed in a 150mL pressure bottle, 1, 8-dibromooctane (1.09g, 4mmol) was dissolved in 10mL of tetrahydrofuran and dropped into the solution, and the reaction was stirred at room temperature for 24 hours, and the solid was removed by suction filtration using a suction flask, and the resulting filtrate was subjected to rotary evaporation to remove the solvent to obtain a crude product and column chromatography on silica gel column, and dichloromethane: petroleum ether =1 was used as a developing agent to obtain 0.57g of solid compound a-1, yield 90%.
Putting compound A-1 (0.32g, 0.5mmol), trimethylamine hydrochloride (0.48g, 5mmol), sodium bicarbonate (0.42g, 5mmol) and 30mL acetonitrile solvent into a 120mL reaction bottle, mixing, heating, stirring, refluxing, reacting for 12h, cooling the reaction liquid, filtering to remove solid, performing rotary evaporation on the filtrate to remove acetonitrile, performing column chromatography on neutral alumina, and purifying by taking dichloromethane: methanol =50 as eluent to obtain 0.19g of a red solid compound B-1; when tested in nitrate solution, a white precipitate rather than a pale yellow precipitate appeared, indicating chloride ion rather than bromide ion in compound B-1. The source of chloride ion is trimethylamine hydrochloride (NMe) 3 HCl) was added in 55% yield as chloride ion was chloride ion instead of bromide ion because of the excess trimethylamine hydrochloride and large electrostatic force of chloride ion to quaternary ammonium nitrogen at the time of charging. 1 H NMR(400MHz,MeOD)δ9.09(dd,J＝8.1,1.2Hz,2H),7.39(td,J＝7.7,1.2Hz,2H),7.01(td,J＝7.8,1.1Hz,2H),6.94(d,J＝7.8Hz,2H),3.78(t,J＝7.1Hz,4H),3.47-3.21(m,4H),3.11(s,18H)1.88-1.59(m,8H),1.39(m,16H). 13 C NMR(100MHz,MeOD)δ169.11,145.98,134.52,133.85,130.86,123.09,122.72,109.59,67.80,53.53,40.75,30.03,29.98,28.35,27.77,27.18,23.84.
Example 2
Isoindigo (0.26g, 1mmol) and potassium hydroxide (0.23g, 4mmol) were dissolved in 10mL of dimethyl sulfoxide, and placed in a 150mL pressure bottle, 1, 6-dibromohexane (0.98g, 4mmol) was dissolved in 10mL of tetrahydrofuran and dropped into the above solution, and the reaction was stirred at room temperature for 24 hours, and the solid was removed by suction filtration with a suction flask, and the resulting filtrate was subjected to rotary evaporation to remove the solvent to obtain a crude product and column chromatography with silica gel column, and methylene chloride: petroleum ether =1 was used as a developing agent to obtain 0.53g of solid compound a-2, yield 90%.
Putting compound A-2 (0.29g, 0.5 mmol), trimethylamine hydrochloride (0.48g, 5 mmol), sodium bicarbonate (0.42g, 5 mmol) and 30mL acetonitrile solvent into a 120mL reaction bottle, mixing, heating, stirring, refluxing and reacting for 12h, cooling the reaction liquid, filtering to remove solids, performing rotary evaporation on the filtrate to remove acetonitrile, performing column chromatography on neutral alumina, and purifying by taking dichloromethane: methanol =50 as an eluent to obtain 0.15g of a red solid compound B-2, wherein the yield is 55%.
Example 3
Isoindigo (0.26g, 1mmol) and potassium hydroxide (0.23g, 4mmol) were dissolved in 10mL of dimethyl sulfoxide, and placed in a 150mL pressure bottle, 1, 4-dibromobutane (0.86g, 4mmol) was dissolved in 10mL of tetrahydrofuran and dropped into the above solution, and the reaction was stirred at room temperature for 24 hours, and the solid was removed by suction filtration with a suction flask, and the resulting filtrate was subjected to rotary evaporation to remove the solvent to obtain a crude product and column chromatography with silica gel column, and dichloromethane: petroleum ether =1 was used as a developing agent to obtain 0.45g of solid compound a-3, yield 85%.
Putting compound A-3 (0.27g, 0.5 mmol), trimethylamine hydrochloride (0.48g, 5 mmol), sodium bicarbonate (0.42g, 5 mmol) and 30mL acetonitrile solvent into a 120mL reaction bottle, mixing, heating, stirring, refluxing and reacting for 12h, cooling the reaction liquid, filtering to remove solids, performing rotary evaporation on the filtrate to remove acetonitrile, performing column chromatography by using a neutral alumina column, and purifying by using dichloromethane: methanol =50 as an eluent to obtain a product, namely 0.12g of a red solid compound B-3, wherein the yield is 50%.
CuSO used in the following examples 4 ·5H 2 O (manufacturer: bailingwei science and technology Co., ltd., specification: 500g, purity: 98%), concentrated sulfuric acid (manufacturer: national drug group chemical reagent Co., ltd., specification: 500mL, purity: 98.08%), and hydrochloric acid (manufacturer: funtang Fine chemical industry Co., ltd., specification: 500mL, content: 36% -38%). Potentiostats (manufacturer: wantong China, switzerland, model: multi Autolab M204), platinum rotating disk electrodes (manufacturer: jiangsu Jiangxi electric analytical instruments Co., ltd., model: ATA-1B), ag/AgCl electrodes (manufacturer: tianjin Idata Hengcheng scientific and technological development Co., ltd., model: RE-1D) platinum wire electrodes (manufacturer: tianjin Idata Hengcheng scientific and technological development Co., ltd., model: pt 017) were used for the tests.
Example 4
The effect of compound B-1 on the copper ion deposition current density was tested.
Preparing CuSO with 60g/L 4 ·5H 2 O、200g/L H 2 SO 4 Under the condition of a rotation speed of 2000 revolutions by taking a Pt rotary electrode as a working electrode, a platinum bar as a counter electrode and Ag/AgCl as a reference electrode in a copper sulfate solution containing 50mg/L chloride ions, solutions of a compound B-1 prepared in the example 1 with different concentrations (the concentrations are respectively 0, 2, 4, 6, 8 and 10 mu mol/L, and the compound B-1 is dissolved in deionized water) are respectively added into the copper sulfate solution containing the chloride ions, and a cathodic polarization curve test is carried out. As shown in FIG. 1, FIG. 1 is a schematic view showing the polarization curve of an electrolyte containing different concentrations of compound B-1, with a scanning speed of 2mVs -1 . The inhibiting effect of compound B-1 prepared according to example 1 on the copper ion deposition on the surface of copper material at different concentrations and the polarization curve of the blank control, with the electrode (Ag/AgCl) potential (unit: volts) on the abscissa and the current density (unit: ampere/square decimeter) on the ordinate. As a result, it was revealed that the compound B-1 increases the cathodic polarization, that when the potential was shifted from positive to negative over 0V without using the compound B-1 prepared in example 1 in the solution, a deposition current of copper was observed, that when the compound B-1 prepared in example 1 was added to the solution, the deposition potential of copper was shifted negative, and that when the compound B-1 prepared in example 1 was used in the solutionWhen the potential of the compound B-1 of (4) was at-0.19V at 4. Mu. Mol/l, a copper deposition current was observed. It can be concluded that compound B-1 can inhibit the deposition of copper ions.
In addition, when JGB and compound B-1 were compared in polarization curves at a concentration of 2. Mu. Mol/l, as shown in FIG. 2, FIG. 2 is a schematic diagram comparing the polarization curves of 2. Mu. Mol/l Kelvin B (a commercial product, hereinafter abbreviated as JGB) and compound B-1, and the scanning speed was 2mVs -1 . As can be seen from FIG. 2, compound B-1 has a significantly more pronounced effect than JGB.
Example 5
The compound B-1 was tested for its ability to inhibit the deposition of copper ions.
Preparing CuSO with 60g/L 4 ·5H 2 O、200g/L H 2 SO 4 A50 mg/L copper sulfate solution containing chloride ions, with a Pt rotary electrode as a working electrode, a platinum rod as a counter electrode and Ag/AgCl as a reference bus, was added to the above copper sulfate solution containing chloride ions at 2000 rpm in the form of solutions of the compound B-1 prepared in example 1 at different concentrations (0, 2, 4, 6, 8. Mu. Mol/L, respectively, and the compound B-1 was dissolved in deionized water) to conduct cyclic voltammetry. As shown in FIG. 3, FIG. 3 is a graph showing the effect of different concentrations of compound B-1 on copper deposition, and the effect of compound B-1 prepared according to example 1 on copper ion deposition inhibition on the surface of copper material at different concentrations and the cyclic voltammogram of a blank control, wherein the abscissa is the electrode (Ag/AgCl) potential (unit: V) and the ordinate is the current density (unit: ampere/dm) 2 ). The results show that the compound B-1 can be adsorbed on the surface of the cathode, and a barrier layer is formed on the surface of the cathode to obstruct the deposition of copper, thereby increasing the resistance of copper deposition reaction, and the inhibiting effect is enhanced with the increase of the concentration of the compound B-1.
Further, when the cyclic voltammograms of compound B-1 and JGB were compared at a concentration of 2. Mu. Mol/l, as shown in FIG. 4, FIG. 4 is a schematic graph showing the cyclic voltammograms of compound B-1 and JGB at a concentration of 2. Mu. Mol/l. The comparison shows that the compound B-1 has better effect than JGB.
Example 6
Compound B-1 was tested as a leveler for its synergistic inhibitory properties with PEG and SPS.
Preparing CuSO with 60g/L 4 ·5H 2 O、200g/L H 2 SO 4 50mg/L of a copper sulfate solution of chloride ions, a Pt rotary electrode as a working electrode, a platinum rod as a counter electrode and Ag/AgCl as a reference electrode, 200ppm of polyethylene glycol PEG (average molecular weight 10000), 1ppm of sodium polydithio dipropyl sulfonate (SPS) and 2ppm of the compound B-1 solution prepared in example 1 (the compound B-1 is dissolved in deionized water) are added into the solution every 1000 seconds at the rotating speed of 100 revolutions per minute and 1000 revolutions per minute respectively to obtain a constant current timing addition curve, as shown in FIG. 5, FIG. 5 is a graph of current density of 2A/dm at different rotating speeds and at different rotating speeds 2 Schematic diagram of galvanostatic addition curve of compound B-1. The compound B-1 prepared according to example 1 was tested by timed addition at different rotational speeds, with the abscissa representing the time (unit: s) and the ordinate representing the potential (unit: volts). As can be seen from FIG. 5, the depolarization phenomenon caused by SPS was suppressed and the potential was shifted negatively by the addition of compound B-1, indicating that compound B-1 still inhibited the deposition of copper in the presence of SPS and PEG. The 1000rpm and 100rpm rotation speeds were used to simulate deposition at the orifice and at the inner wall of the via, respectively. The potential difference at different rpm was defined as Δ η = η (100 rpm) - η (1000 rpm), while Δ η 2=18mv was positive and greater than Δ η 1=6mv (Δ η 2 and Δ η 1 represent the potential difference at different rpm after addition of compound B-1 and SPS, respectively), indicating that the adsorption behavior of compound B-1 is a convection-dependent adsorption, used to characterize the difference in inhibition at 1000rpm and 100 rpm. If Δ η is positive, it indicates that strong convection results in less copper deposition and is suitable for plating with vias. Therefore, the adsorption of compound B-1 at the hole opening of the PCB (the PCB is a printed circuit board having a through hole, used for actual copper plating) is stronger than that at the middle position of the hole, suppressing the deposition of copper at the hole opening. Under the synergistic action of PEG and SPS, a plating layer with uniform thickness distribution can be obtained during electroplating, and as can be seen from FIG. 5, the inhibition effect of the rotating disk electrode is different under different rotating speeds, namely the deposition potential difference is about 18mV, wherein the inhibition effect is different between the rotating disk electrode and the rotating disk electrode.
Although the present invention has been described with reference to a preferred embodiment, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (6)
1. An isoindigo quaternary ammonium compound, which is characterized in that the structural formula is shown as a general formula B:
wherein R is 1 is-H; r 2 Is composed of
n is 2, 3, 4, 5, 6 or 8; y is Cl, br, F, I.
2. The isoindigo quaternary ammonium salt compound according to claim 1, wherein R is 2 Is composed of
n is 2, 4, 6; y is Cl, br, F, I.
3. The isoindigo quaternary ammonium salt compound according to claim 2, wherein the isoindigo quaternary ammonium salt compound has the following structural formula:
4. a method for preparing isoindigo quaternary ammonium salt compound according to any one of claims 1 to 3, comprising the steps of:
R 1 is-H; y is Cl, br, F, I; x is Br;
mixing unsubstituted isoindigo, alkyl halide and alkali with a proper solvent according to a molar ratio of 1 (2-10) to (2-10), reacting for 1-24 h, performing suction filtration, performing rotary evaporation on filtrate to remove the solvent to obtain a crude product, and performing column chromatography to obtain a compound A;
mixing the compound A, trimethylamine hydrochloride and sodium bicarbonate with the molar ratio of 1 (2-12) to (2-12) with a proper solvent, heating, stirring, refluxing and reacting for 1-24 h, cooling, filtering, removing the solvent from the filtrate by rotary evaporation, and performing column chromatography to obtain the isoindigo quaternary ammonium salt compound, namely the compound B;
wherein the alkyl halide is 1, 8-dibromooctane, 1, 6-dibromohexane or 1, 4-dibromobutane; the alkali is potassium hydroxide or sodium hydroxide.
5. The method for preparing isoindigo quaternary ammonium salt compound according to claim 4, wherein the solvent is selected from the group consisting of: at least one of tetrahydrofuran, dimethyl sulfoxide, and acetonitrile; the mol ratio of the unsubstituted isoindigo to the alkyl halide to the base is 1; the molar ratio of the compound A, trimethylamine hydrochloride and sodium bicarbonate is 1.
6. Use of the isoindigo quat compound according to any one of claims 1 to 3 as a plating leveler.
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