Dimeric xanthene dye for blue photoresist color paste and synthesis method of dimeric xanthene dye

Abstract

The invention belongs to the field of color photoresists, and particularly provides a dimeric xanthene dye for blue photoresist color paste and a synthesis method of the dimeric xanthene dye. The dimeric xanthene dye for the blue photoresist color paste is prepared by acidifying an acid red 52 dye, then carrying out sulfonyl chlorination reaction with a chlorination reagent, and then carrying out dimerization reaction with a double-nucleophilic reaction site compound. The prepared dimeric xanthene dye is mixed with blue pigment color paste to prepare blue photoresist color paste, the blue photoresist color paste is used for improving the brightness of the color paste, and the blue photoresist color paste has the advantages of high transparency, high contrast ratio, good dispersity, relatively high covering power, tinting strength and the like, and is good in thermal stability and light stability; the synthesis method provided by the invention is simple, low in cost and easy for large-scale production.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of color photoresist, and particularly relates to a novel dimer xanthene dye for blue photoresist color paste and a synthesis method thereof. BACKGROUND

[0002] In the field of flat panel display manufacturing, the performance of the color filter (CF) of TFT-LCD plays a crucial role in the color performance of the display. At present, the industry mainly uses a pigment nanodispersion liquid type photoresist system to prepare the color filter. Although this system has certain advantages, such as good weather resistance and initial color saturation, it also has obvious defects. Due to the low solubility of pigment molecules, large-size agglomerates are easily formed in the photoresist. These agglomerates can cause serious backlight scattering, thereby significantly reducing the contrast of the color filter, and also increasing energy consumption. With the continuous development of display technology, the new generation of display technology has put forward more stringent requirements for wide color gamut and low power consumption, and the existing pigment nanodispersion liquid type photoresist system is difficult to meet these requirements.

[0003] In order to realize precise spectral regulation, the color filter needs to rely on the selective absorption characteristics of the colorant molecules, and its working wavelength range is usually in the visible light range of 380-780 nm. Xanthene dyes are considered as ideal candidate materials for color filter colorants due to their wide spectral range (covering yellow-blue-red region), high molar extinction coefficient, excellent fluorescence characteristics, and structural adjustability. However, in the existing technology, there is still a lack of a solution that combines high stability, easy synthesis, and excellent dispersion for blue xanthene dyes. SUMMARY

[0004] The present application aims to overcome the technical defects in the background art, and provides a novel dimer xanthene dye for blue photoresist color paste and a synthesis method thereof. The xanthene dye can be mixed with blue pigment color paste to form blue photoresist color paste to improve the brightness of the color paste. It has high transparency, high contrast, good dispersibility, high hiding power, coloring power and other advantages, and has good thermal stability and light stability. At the same time, the synthesis method provided by the present application is simple, low in cost, and easy to scale up.

[0005] The present application first provides a dimer xanthene dye for blue photoresist color paste, and the chemical structure of the dimer xanthene dye (A) is as follows: ; wherein X represents a linker containing a double-nucleophilic functional group.

[0006] Preferably, the linker containing a double-nucleophilic functional group includes an alkyl substituent containing at least one of N, O, and S, or an aryl substituent containing at least one of N, O, and S.

[0007] Preferably, the alkyl or aryl substituents have 1 to 20 carbon atoms.

[0008] Preferably, the hydrogen atoms contained in the alkyl substituent or aryl substituent can be replaced by halogen atoms, the -CH- contained in the alkyl substituent can be replaced by -CO- or -O-, and the aryl substituent can be a common aromatic, aromatic fused ring, or aromatic heterocyclic ring.

[0009] Secondly, this application provides a method for synthesizing the above-mentioned dimer xanthan dye for blue photoresist pigment paste, comprising the following steps: (1) Acidification: Dissolve Acid Red 52 dye in water, then add concentrated hydrochloric acid dropwise to carry out the acidification reaction, filter, and obtain acidified dye B; (2) Acyl chloride reaction: Acidified dye B and chlorinating reagent are reacted in a solvent to carry out acyl chloride reaction to obtain sulfonyl chloride intermediate C; (3) Dimerization reaction: The sulfonyl chloride intermediate C is dimerized with the amphiphilic reaction site compound to finally obtain dimer saxon dyes.

[0010] Preferably, in step (1), the molar ratio of Acid Red 52 dye to concentrated hydrochloric acid is 1:1 to 1:1.5, more preferably 1:1 to 1:1.2.

[0011] Preferably, in step (2), the molar ratio of the acidified dye B to the chlorinating reagent is 1:1 to 1:20, more preferably 1:5 to 1:10.

[0012] Preferably, the chlorinating agent includes any one or more of thionyl chloride, oxalyl chloride, phosphorus trichloride, phosphorus oxychloride, and phosphorus pentachloride, more preferably any one of phosphorus oxychloride and thionyl chloride.

[0013] Preferably, in step (2), the solvent includes any one or more of dichloroethane, toluene, and xylene.

[0014] Preferably, in step (2), the sulfonyl chlorination reaction is carried out using the catalyst N,N-dimethylformamide (DMF).

[0015] Preferably, in step (2), the temperature of the sulfonyl chlorination reaction is 0℃~150℃, more preferably 60℃~110℃.

[0016] Preferably, in the dimerization reaction of step (3), the molar ratio of the sulfonyl chloride intermediate C to the compound at the binucleophilic reaction site is 2:1 to 4:1, more preferably 2:1 to 3:1.

[0017] Preferably, in the dimerization reaction described in step (3), the nucleophilic group of the compound with the binucleophilic reaction site is any one or more of amino, hydroxyl, mercapto, carboxylic acid or amide groups, more preferably any one or more of amino, hydroxyl or mercapto groups.

[0018] Preferably, in the dimerization reaction described in step (3), the linking group of the amphiphilic reaction site compound is an alkyl substituent or an aryl substituent, more preferably an alkyl substituent.

[0019] Preferably, in the dimerization reaction described in step (3), an alkali is added, and the molar ratio of sulfonyl chloride intermediate C to the alkali is 1:1 to 1:9, more preferably 1:1 to 1:6.

[0020] Preferably, in the dimerization reaction described in step (3), the base is any one or more of triethylamine, pyridine, piperidine, 4-dimethylaminopyridine (DMAP), 1,8-diazabicyclo[5.4.0]undec-7-ene, and diisopropylethylamine, more preferably any one of triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene, and diisopropylethylamine.

[0021] Preferably, a solvent is used in the dimerization reaction described in step (3).

[0022] Preferably, in the dimerization reaction described in step (3), the solvent is one or more of toluene, tetrahydrofuran, dichloromethane (DCM), chloroform, or dichloroethane, more preferably any one of tetrahydrofuran and dichloromethane.

[0023] Preferably, in the dimerization reaction described in step (3), the temperature of the dimerization reaction is -20℃ to 80℃, more preferably 0℃ to 40℃.

[0024] Thirdly, this application provides an application of the above-mentioned dimer zeolite dye for blue photoresist color paste, wherein the dimer zeolite dye is used in blue photoresist color paste.

[0025] Compared with the prior art, this application has the following beneficial effects: 1. The dimer succinyl dyes provided in this application significantly improve light and heat resistance through their dimer structure, effectively resisting the effects of light and high temperature environments, extending the service life of photoresist pigments, and reducing production costs.

[0026] 2. This application utilizes the molecular steric hindrance and lipid-soluble groups brought about by the dimerization reaction to greatly improve the solubility and dispersibility of dimer succinate dyes in photoresist, avoid the occurrence of agglomeration, and improve the optical properties such as brightness and contrast of photoresist pigments.

[0027] 3. The synthesis method provided in this application has a simple route, widely available reagents, low cost, and is easy to scale up for production. It can meet the stringent requirements of the new generation of photolithography processes for photoresist pigments and has broad application prospects. Attached Figure Description

[0028] Figure 1 This is a synthetic route diagram for the dimeric zeatan dyes of this application.

[0029] Figure 2 The compound A1 prepared in Example 1 of this application 1 H-NMR spectrum.

[0030] Figure 3 The compound A2 prepared in Example 2 of this application 1 H-NMR spectrum.

[0031] Figure 4 The compound A3 prepared in Example 3 of this application 1 H-NMR spectrum. Detailed Implementation

[0032] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of this application.

[0033] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0034] When using “including,” “having,” and “contains” as described herein, the intention is to cover non-exclusive inclusion, unless an explicit qualifying term such as “only,” “consisting of,” etc., is used, in which case another component may be added.

[0035] The terms "preferred," "more preferably," "better," and "even better" used in this application refer to embodiments of this application that provide certain beneficial effects under certain circumstances. However, other embodiments may also be preferred under the same or other circumstances. Furthermore, the description of one or more preferred embodiments does not imply that other embodiments are unavailable, nor is it intended to exclude other embodiments from the scope of this application. That is, in this application, "preferred," "more preferably," "better," and "even better" are merely descriptions of implementations or embodiments with better effects, but do not constitute a limitation on the scope of protection of this application.

[0036] In this application, terms such as "further," "even more," and "particularly" are used for descriptive purposes and indicate differences in content, but should not be construed as limiting the scope of protection of this application.

[0037] In this application, "at least one" means one or more, such as one, two, or more. "Multiple" or "several" means at least two, such as two, three, etc., and "multi-layered" means at least two layers, such as two layers, three layers, etc., unless otherwise explicitly specified. In the description of this application, "several" means at least one, such as one, two, etc., unless otherwise explicitly specified.

[0038] When a numerical range is disclosed herein, the range is considered continuous and includes the minimum and maximum values ​​of the range, as well as every value between the minimum and maximum values. Furthermore, when the range refers to integers, it includes every integer between the minimum and maximum values ​​of the range. Additionally, when multiple ranges are provided to describe a feature or characteristic, the ranges may be combined. In other words, unless otherwise specified, all ranges disclosed herein should be understood to include any and all subranges to which they are incorporated.

[0039] Unless otherwise specified, all steps in this application may be performed sequentially or randomly. For example, the method comprising steps (a) and (b) indicates that the method may include steps (a) and (b) performed sequentially, or it may include steps (b) and (a) performed sequentially. For example, the mention that the method may also include step (c) indicates that step (c) may be added to the method in any order; for example, the method may include steps (a), (b), and (c), or it may include steps (a), (c), and (b), or it may include steps (c), (a), and (b), etc. Unless otherwise stated, singular terms may include plural forms and should not be construed as having a quantity of one.

[0040] In this application, "above" or "below" includes the number itself. For example, "below 1" includes 1.

[0041] This application, based on extensive experimental research, provides a dimerized xanthan dye for blue photoresist color paste and its synthesis method. Through innovative molecular design and simplified processes, Acid Red 52 dye is acidified, then subjected to sulfonyl chlorination with a chlorinating agent, followed by dimerization with a compound containing amphiphilic nucleophilic sites, ultimately yielding a novel dimerized xanthan dye. This dimerized structure significantly improves the weather resistance of the molecule. Under light and high-temperature environments, the dimerized xanthan dye molecules maintain a stable chemical structure, are not prone to decomposition or discoloration, thus ensuring the long-term stability of the photoresist color paste. Simultaneously, the dimerization results in greater molecular steric hindrance, and the molecule itself possesses numerous lipid-soluble groups, effectively improving the solubility and dispersibility of the dye molecules. The greater molecular steric hindrance prevents excessive aggregation between dye molecules, while the lipid-soluble groups facilitate the dissolution of dye molecules in organic solvents, enabling uniform dispersion in the photoresist, improving contrast and brightness, and effectively overcoming technical barriers.

[0042] The zeatin dyes prepared in this application can be mixed with other colorants to form mixed or dye-type blue photoresist pastes, which can be used to improve the various properties of the pastes, such as brightness, contrast and weather resistance.

[0043] In some embodiments of this application, the molar ratio of Acid Red 52 dye to concentrated hydrochloric acid is 1:1 to 1:1.5.

[0044] In some specific embodiments of this application, the molar ratio of Acid Red 52 dye to concentrated hydrochloric acid can be 1:1 to 1:1.2, 1:2 to 1:1.3, 1:3 to 1:1.4, or 1:4 to 1:1.5; typically, but not limitingly, it can be 1:1 or 1:1.2.

[0045] In some specific embodiments of this application, the molar ratio of the acidifying dye B to the chlorinating reagent can be 1:1 to 1:5, 1:5 to 1:10, 1:10 to 1:15, or 1:15 to 1:20; typically, but not limitingly, it can be 1:5, 1:7, 1:8, or 1:10.

[0046] In some specific embodiments of this application, the temperature of the sulfonyl chlorination reaction can be 0℃~30℃, 30℃~60℃, 60℃~110℃, or 110℃~150℃, typically but not limitingly, for example, 60℃, 90℃, or 110℃.

[0047] In some specific embodiments of this application, the nucleophilic group of the amphiphilic reactive site compound is any one or more of amino, hydroxy, mercapto, carboxylic acid, or amide groups. The linking group of the amphiphilic reactive site compound is an alkyl substituent or an aryl substituent such as a common aromatic, aromatic fused ring, or aromatic heterocyclic group. The number of carbon atoms in the alkyl or aryl substituent is any integer value between 1 and 20. The hydrogen atoms contained in the alkyl or aryl substituent can be replaced by halogen atoms, and the -CH- in the alkyl substituent can be replaced by -CO- or -O-. Typical, but not limiting, examples include 1,4-butanediamine, 1,4-butanediol, and 2,2'-oxydiethylamine.

[0048] In some specific embodiments of this application, the chlorinating agent can be any one or more of thionyl chloride, oxalyl chloride, phosphorus trichloride, phosphorus oxychloride, and phosphorus pentachloride; typically, but not limitingly, for example, the chlorinating agent can be oxalyl chloride or thionyl chloride.

[0049] In some specific embodiments of this application, in the dimerization reaction described in step (3), the base can be any one or more of triethylamine, pyridine, piperidine, 4-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]undec-7-ene, and diisopropylethylamine; typically, but not limitingly, the base can be triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene, or diisopropylethylamine.

[0050] In some specific embodiments of this application, the molar ratio of sulfonyl chloride intermediate C to base can be 1:1 to 1:3, 1:3 to 1:6, or 1:6 to 1:9; typically, but not limitingly, it can be 1:1, 1:2, 1:3, 1:4, 1:5, or 1:6.

[0051] In some specific embodiments of this application, the temperature of the dimerization reaction can be -20℃ to 0℃, 0℃ to 20℃, 20℃ to 40℃, or 40℃ to 80℃. Typical but not limiting examples are 0℃, 20℃, and 40℃.

[0052] The present application will be further illustrated by the following examples, but these examples do not limit the scope of the present application.

[0053] When numerical ranges are given in the embodiments, it should be understood that, unless otherwise stated in this application, both endpoints of each numerical range and any value between the two endpoints may be selected. Unless otherwise defined, all technical and scientific terms used in this application have the same meaning as commonly understood by one of ordinary skill in the art. Where specific conditions are not specified in the embodiments, conventional conditions or conditions recommended by the manufacturer shall apply. All reagents or instruments whose manufacturers are not specified are conventional products that can be purchased commercially. In addition to the specific methods, equipment, and materials used in the embodiments, based on the knowledge of the prior art possessed by one of ordinary skill in the art and the description in this application, any prior art methods, equipment, and materials similar to or equivalent to those described, used, or made by the methods, equipment, and materials in the embodiments of this application may be used to implement this application.

[0054] The synthesis routes of dimer succinyl dyes for blue photoresist color pastes in Examples 1-3 are as follows: Figure 1 As shown.

[0055] Example 1 The synthesis method of the dimer xanthan dye (compound A1) for the blue photoresist pigment paste in this embodiment is as follows: (1) Take a dry and clean 500mL two-necked flask and place a stir bar of appropriate size; add Acid Red 52 (58g, 100mmol, 1.0eq) and an appropriate amount of deionized water. After stirring continuously for 20min, slowly add concentrated hydrochloric acid. After the acidification reaction is complete, filter to obtain acidified dye B (52.7g, yield 90.8%).

[0056] (2) Take a dry and clean 1000 mL two-necked flask and place a stir bar of appropriate size; add the acidified dye B obtained in the previous step (50 g, 87.5 mmol, 1.0 eq), dry DCM solvent (500 mL) and DMF (5.0 mL), and stir in an ice-water bath for 30 minutes; then, under a nitrogen atmosphere and ice-water bath conditions, add oxalyl chloride (111 g, 875 mmol, 10 eq) dropwise to the above system; after the oxalyl chloride is added, slowly raise the above reaction system to room temperature and react at room temperature for 24 hours; after the reaction is completed, filter, and then distill under reduced pressure to obtain sulfonyl chloride intermediate C (38.5 g, yield 74.7%). The chemical structural formula of intermediate C is as follows: .

[0057] (3) Take a clean 250 mL three-necked flask and place a stir bar of appropriate size; add the sulfonyl chloride intermediate C (9.31 g, 15.8 mmol, 3.0 eq), 1,4-butanediamine (460 mg, 5.27 mmol, 1.0 eq), DMAP (2.5 mg, 0.02 mmol, 0.004 eq) obtained in the previous step, and add dry DCM solvent (100 mL), and stir in an ice-water bath for 15 minutes; then, under a nitrogen atmosphere and ice-water bath conditions, add triethylamine (1.59 g, 15.8 mmol, 3.0 eq) dropwise to the above system; after the triethylamine is added, slowly raise the above reaction system to room temperature and react overnight at room temperature; the next day, when the reaction is completed, filter, then distill under reduced pressure, recrystallize to obtain a purple-red xanthan dye compound A1 (4.71 g solid, yield 76.5%).

[0058] The chemical structural formula of compound A1 is as follows: .

[0059] The compound A1 1 The H-NMR spectrum is shown below. Figure 2 .

[0060] Example 2 The synthesis method of the dimer xanthan dye (compound A2) for the blue photoresist pigment paste in this embodiment is as follows: The sulfonyl chloride intermediate C was prepared according to steps (1) and (2) in Example 1.

[0061] Take a clean 250 mL three-necked flask and place a stir bar of appropriate size; add the obtained sulfonyl chloride intermediate C (9.31 g, 15.8 mmol, 3.0 eq), 1,4-butanediol (474 ​​mg, 5.27 mmol, 1.0 eq), DMAP (2.5 mg, 0.02 mmol, 0.004 eq), and add 100 mL of dry DCM solvent, and stir in an ice-water bath for 15 minutes; then, under a nitrogen atmosphere and ice-water bath conditions, add triethylamine (1.59 g, 15.8 mmol, 3.0 eq) dropwise to the above system; after the triethylamine is added, slowly raise the above reaction system to room temperature and let it react overnight at room temperature; the next day, when the reaction is complete, filter, then distill under reduced pressure, and recrystallize using a dichloromethane mixed solvent to give a purple-red xanthones dye compound A2 (5.13 g solid, yield 83.1%).

[0062] The chemical structural formula of compound A2 is as follows: .

[0063] The compound A2 1 The H-NMR spectrum is shown below.Figure 3 .

[0064] Example 3 The synthesis method of the dimer xanthan dye (compound A3) for the blue photoresist pigment paste in this embodiment is as follows: The sulfonyl chloride intermediate C was prepared according to steps (1) and (2) in Example 1.

[0065] Take a clean 250 mL three-necked flask and place a stir bar of appropriate size; add the obtained sulfonyl chloride intermediate C (9.31 g, 15.8 mmol, 3.0 eq), 2,2'-oxydiethylamine (549 mg, 5.27 mmol, 1.0 eq), DMAP (2.5 mg, 0.02 mmol, 0.004 eq), and add 100 mL of dry DCM solvent, and stir in an ice-water bath for 15 minutes; then, under a nitrogen atmosphere and ice-water bath conditions, add triethylamine (1.59 g, 15.8 mmol, 3.0 eq) dropwise to the above system; after the triethylamine is added, slowly raise the above reaction system to room temperature and let it react overnight at room temperature; the next day, when the reaction is complete, filter, then distill under reduced pressure, recrystallize to give a purple-red xanthones dye compound A3 (4.89 g solid, yield 78.5%).

[0066] The chemical structural formula of compound A3 is as follows: .

[0067] The compound A3 1 The H-NMR spectrum is shown below. Figure 4 .

[0068] Control group 1 The synthesis method of the blue photoresist pigment paste used in this control group, which uses a dimerized xanthan dye (compound A4), is as follows: The sulfonyl chloride intermediate C was prepared according to steps (1) and (2) in Example 1.

[0069] Take a clean 500 mL three-necked flask and place a stir bar of appropriate size; add the obtained sulfonyl chloride intermediate C (5.8 g, 10 mmol, 1.0 eq), n-butylamine (804 mg, 11 mmol, 1.1 eq), DMAP (5 mg, 0.04 mmol, 0.004 eq), and add dry DCM solvent (75 mL), and stir in an ice-water bath for 15 minutes; then, under a nitrogen atmosphere and ice-water bath conditions, add triethylamine (1.1 g, 11 mmol, 1.1 eq) dropwise to the above system; after the triethylamine is added, slowly raise the above reaction system to room temperature and let it react overnight at room temperature; the next day, when the reaction is complete, filter, then distill under reduced pressure, recrystallize to give a purple-red xanthones dye compound A4 (4.35 g solid, yield 71%).

[0070] The chemical structural formula of compound A4 is as follows: .

[0071] Performance testing I. Determination of UV-Vis Absorption Spectroscopy of Xanthan Dyes The xanthan dyes prepared in Examples 1-3 and Comparative Example 1 were formulated into 10 μmol / L solutions using propylene glycol methyl ether acetate (PGMEA) as the solvent, and their absorption spectra were measured using a UV-Vis spectrophotometer. The molar extinction coefficient of the dyes was calculated using the following formula: Α=εcl In the formula, A is the absorption intensity; ε is the molar extinction coefficient, L / (mol·cm); c is the concentration, mol / L; and l is the thickness of the absorption layer, cm.

[0072] The UV-Vis absorption spectra of the xanthanna dyes prepared in Examples 1 to 3 and Comparative Example 1 are shown in Table 1.

[0073] Table 1. UV-Vis absorption spectra of the xanthannae dyes prepared in Examples 1-3 and Comparative Example 1. As can be seen from Table 1, the xanthan dyes prepared in Examples 1 to 3 are slightly red-shifted compared to Comparative Example 1. The xanthan dye molecules prepared in Example 3 are red-shifted compared to Example 1, and the xanthan dye prepared in Example 3 has the highest molar absorptivity.

[0074] II. Solubility Test of Xanthan Dyes The solubility of xanthan dyes prepared in Examples 1-3 and Comparative Example 1 in PGMEA and DMF was tested. A certain amount of xanthan dye and organic solvent were weighed, sonicated at room temperature for 10 min, and allowed to stand for 24 h. The mixture was then filtered three times using a filter membrane. The filtrate was dried, and the solubility S of the xanthan dye was calculated. S=100MS / ML In the formula, MS is the mass of the dried xanthan dye, in g; ML is the mass of the solution, in g.

[0075] The solubility test results of the xanthan dyes prepared in Examples 1 to 3 and Comparative Example 1 are shown in Table 2.

[0076] Table 2. Solubility test results of xanthan dye molecules prepared in Examples 1-3 and Comparative Example 1 As shown in Table 2, compared with Comparative Example 1, the xanthan dye molecules prepared in Examples 1 to 3 all have better solubility in PGMEA and DMF, among which the xanthan dye molecules prepared in Example 3 have the best solubility in PGMEA and DMF.

[0077] III. Thermal stability test of xanthan dyes The fabrication of color filters involves a post-baking process at 200°C or higher, as industrial applications require dye molecules to exhibit good thermal stability at this temperature. Thermogravimetric analysis (TGA) was used to evaluate the thermal stability of the xanthan dyes prepared in Examples 1-3 and Comparative Example 1. The xanthan dyes were heated from room temperature to 500°C under nitrogen protection at a heating rate of 10°C / min to determine their thermal decomposition temperature T. d The thermal stability test results of the xanthan dyes prepared in Examples 1 to 3 and Comparative Example 1 are shown in Table 3.

[0078] Table 3. Thermal stability test results of xanthan dye molecules prepared in Examples 1-3 and Comparative Example 1. As shown in Table 3, the T values ​​of the xanthan dyes prepared in Examples 1 to 3 are... d Within the temperature range of 310~346℃, the weight loss rate at 230℃ is less than 5%, indicating that the xanthan dyes of this application have good thermal stability.

[0079] The novel xanthan dye prepared in this application is particularly suitable for formulating high-performance blue photoresist color pastes. This dye not only significantly improves the brightness of the color paste but also possesses the following excellent properties: outstanding optical performance, excellent dispersibility, and superior color strength. Furthermore, the compound exhibits remarkable thermal stability. In terms of the preparation process, the operation procedure developed in this invention is simple and efficient, with significant advantages in production cost, making it very suitable for large-scale industrial production.

[0080] Although this application has been described in detail with reference to the foregoing embodiments, those skilled in the art can still modify the technical solutions described in the foregoing embodiments or make equivalent substitutions for some of the technical features. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of this application should be included within the protection scope of this application.

Claims

1. A dimerized xanthan dye for blue photoresist pigment paste, characterized in that: The general chemical structural formula of the dimer xanthan dyes is as follows: In the formula, X represents a linker containing a functional group with amphiphilic nuclei.

2. The dimerized xanthan dye for blue photoresist pigment paste according to claim 1, characterized in that: The linker containing a nucleophilic functional group includes an alkyl substituent containing at least one element of N, O, or S, or an aryl substituent containing at least one element of N, O, or S.

3. A method for synthesizing a dimerized xanthan dye for blue photoresist pigment as described in claim 1 or 2, characterized in that: Includes the following steps: (1) Acidification: Dissolve Acid Red 52 dye in water, then add concentrated hydrochloric acid dropwise to carry out the acidification reaction, filter, and obtain acidified dye B; (2) Acyl chloride reaction: Acidified dye B and chlorinating reagent are reacted in a solvent to carry out acyl chloride reaction to obtain sulfonyl chloride intermediate C; (3) Dimerization reaction: The sulfonyl chloride intermediate C is dimerized with the amphiphilic reaction site compound to finally obtain dimer saxon dyes.

4. The method for synthesizing dimer succinate-based dyes for blue photoresist pigments according to claim 3, characterized in that: In step (1), the molar ratio of Acid Red 52 dye to concentrated hydrochloric acid is 1:1 to 1:1.

5.

5. The method for synthesizing dimer zeolite dyes for blue photoresist pigments according to claim 3, characterized in that: In step (2), the molar ratio of the acidified dye B to the chlorinating reagent is 1:1 to 1:20; And / or, the chlorinating agent includes any one or more of thionyl chloride, oxalyl chloride, phosphorus trichloride, phosphorus oxychloride, and phosphorus pentachloride.

6. The method for synthesizing dimer succinate-based dyes for blue photoresist pigments according to claim 3, characterized in that: In step (2), the solvent includes any one or more of dichloroethane, toluene, and xylene; And / or, in step (2), the sulfonyl chlorination reaction is carried out using the catalyst N,N-dimethylformamide; And / or, in step (2), the temperature of the sulfonyl chlorination reaction is 0℃~150℃.

7. The method for synthesizing dimer zeolite dyes for blue photoresist pigments according to claim 3, characterized in that: In the dimerization reaction described in step (3), the molar ratio of the sulfonyl chloride intermediate C to the compound with the binucleophilic reaction site is 2:1 to 4:1; And / or, in the dimerization reaction described in step (3), the nucleophilic group of the compound with the binucleophilic reaction site is any one or more of amino, hydroxyl, and thiol groups; And / or, in the dimerization reaction described in step (3), the linking group of the amphiphilic reaction site compound is an alkyl substituent or an aryl substituent.

8. The method for synthesizing dimer succinate-based dyes for blue photoresist pigments according to claim 6, characterized in that: In step (3), an alkali is added to the dimerization reaction; And / or, a solvent is used in the dimerization reaction described in step (3); And / or, in the dimerization reaction described in step (3), the temperature of the dimerization reaction is -20℃ to 80℃.

9. The method for synthesizing dimer succinate-based dyes for blue photoresist pigments according to claim 8, characterized in that: In the dimerization reaction described in step (3), the base is any one or more of triethylamine, pyridine, piperidine, 4-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]undec-7-ene, and diisopropylethylamine; And / or, in the dimerization reaction described in step (3), the solvent is one or more of toluene, tetrahydrofuran, dichloromethane, chloroform or dichloroethane.

10. An application of a dimerized xanthan dye for blue photoresist pigments as described in claim 1 or 2, characterized in that: Used for blue photoresist color paste.

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