A green phthalocyanine dye with high solubility for photoresist and a method for synthesizing the same

Abstract

The application discloses a kind of high solubility green phthalocyanine dyes for photoresist and a synthesis method thereof, the synthesis method comprises the following steps: (1) S N Ar reaction: under the action of catalyst, attack aromatic ring using carboxyl compound to carry out S N Ar reaction, and after treatment to obtain intermediate P1;(2) preparation of phthalocyanine dye: using intermediate P1 obtained in step (1), metal salt, high-boiling alcohol as raw material, and under the activation condition of catalyst, reaction, after treatment to obtain phthalocyanine P2. The application provides a new type of high solubility phthalocyanine dye molecule, which can be mixed with other colorants to configure green photoresist color paste, which has phthalocyanine as parent structure, improves dye solubility by introducing halogen atom, alkoxycarbonyl, etc., and has excellent thermal stability and light stability;At the same time, the synthesis method provided by the application is simple, easy to mass production, and can be used to improve the quality of LCD display.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of color paste for color photoresist, and particularly relates to a green phthalocyanine dye for photoresist with high solubility and a synthesis method thereof. BACKGROUND

[0002] Liquid crystal display has become the mainstream product in the flat panel display market due to its low voltage, low power consumption, long service life, no radiation, no pollution and other technical advantages. The color filter is the core component for realizing the pattern color of the liquid crystal display. When the light source passes through the color filter, it is converted into red, green and blue three primary colors, and full-color display is realized through the mixing of the three primary colors. The color filter is composed of a glass substrate, a black matrix, a color layer, an ITO conductive film and a transparent protective glue, wherein the color layer plays a decisive role in color display.

[0003] The green filter colorant is generally a phthalocyanine compound. Phthalocyanine is an aromatic heterocycle composed of four isoindole rings bridged by nitrogen atoms, and has strong π-π electron interaction, so it has rich photo-physical / photo-chemical properties and significant stability. Correspondingly, the strong intermolecular interaction force also leads to poor dispersibility in organic solvents (such as esters and ketones), and easy formation of aggregates, which in turn affects the light transmittance and color purity of the filter, and may even cause uniformity problems in the coating process, resulting in color spots or uneven brightness on the display panel.

[0004] Therefore, it is of great significance to develop phthalocyanine dyes with excellent solubility and high photo-thermal stability for overcoming the low solubility of current phthalocyanine dyes, and for developing a new generation of color filters. SUMMARY

[0005] The technical problem to be solved by the present application is to overcome the technical defects of the background art, and to provide a green phthalocyanine dye for photoresist with high solubility and a synthesis method thereof. The present application provides a novel phthalocyanine dye molecule with high solubility. The phthalocyanine dye molecule can be mixed with other colorants to configure a green photoresist color paste. The color paste has a phthalocyanine parent structure, and halogen atoms, alkoxycarbonyl groups and the like are introduced to improve the solubility of the color paste. The color paste has excellent thermal stability and light stability. The synthesis method provided by the present application is simple and easy to scale up, and can be used to improve the quality of LCD display.

[0006] The technical solution adopted by the present application to solve the above technical problems is as follows:

[0007] A green phthalocyanine dye for photoresist with high solubility. Due to the presence of halogen atoms, alkoxycarbonyl groups and the like in the molecule, the compatibility of the dye molecule with the commonly used solvent propylene glycol methyl ether acetate for the filter is increased, thereby improving the solubility of the dye. The chemical structural formula of the green phthalocyanine dye is shown in general formula I:

[0008] ;

[0009] The symbols in the formula represent the following meanings: Mn represents a metal atom, which is not limited, and can be exemplified by copper, zinc, cobalt, etc., R 1 is a hydrogen atom, R 2 is a halogen atom, R 3 is a structure represented by general formula II, x+y+z=16, 0≤x≤15, 0≤y≤15, 1≤z≤16, R 4 -R 8 represents an arbitrary substituent, which is not limited, and can be exemplified by a hydrogen atom, a halogen atom, an alkoxy group, an alkoxycarbonyl group, an aryl group, a nitro group, etc.

[0010] The synthesis method of the high-solubility green phthalocyanine dye for photoresist as described above comprises the following steps:

[0011] (1) S N Ar reaction: under the action of a catalyst, a carboxyl compound attacks an aromatic ring to perform S N Ar reaction, and an intermediate P1 is obtained after treatment;

[0012] (2) Preparation of phthalocyanine dye: using the intermediate P1 obtained in step (1), a metal salt, and a high-boiling alcohol as raw materials, and under the activation condition of a catalyst, a reaction is performed, and a phthalocyanine P2 is obtained after treatment.

[0013] The above synthesis route is as follows:

[0014] ;

[0015] The symbols in the formula represent the following meanings:

[0016] Mn represents a metal atom, which is not limited, and can be exemplified by copper, zinc, cobalt, etc.; R 4 -R 8 represents an arbitrary substituent, which is not limited, and can be exemplified by a hydrogen atom, a halogen atom, an alkoxy group, an alkoxycarbonyl group, an aryl group, a nitro group, etc.; R 9 -R 12 independently represent H, F, Cl, NO2, etc.

[0017] Preferably, in step (1), the catalyst during the reaction can be selected from any one or combination of alkali substances such as potassium carbonate, sodium carbonate, potassium hydroxide, and sodium hydroxide, and more preferably any one or combination of potassium carbonate and sodium carbonate.

[0018] Preferably, in step (1), the organic solvent during the reaction can be selected from any one or combination of N,N-dimethylformamide, acetone, toluene, and xylene, and more preferably any one or combination of N,N-dimethylformamide and acetone.

[0019] Preferably, in step (1), the molar ratio of S1 to S2 is 1:1-1:10, more preferably 1:1-1:5.

[0020] Preferably, in step (1), the molar ratio of S1 to the catalyst is 1:1-1:10, more preferably 1:1-1:5.

[0021] Preferably, in step (1), the reaction temperature is -20-120℃, more preferably 0-80℃.

[0022] Preferably, in step (1), the reaction time is 1h-7d, more preferably 8h-2d.

[0023] Preferably, in step (1), the post-treatment method is: after the reaction is stopped, cooling to room temperature, stirring the cooling liquid and ice water uniformly, and then filtering to obtain a filter cake, and then column chromatography separation is performed on the filter cake to obtain the purified intermediate P1; or the reaction liquid cooled to room temperature is extracted with dichloromethane, washed with saturated brine and dried with anhydrous sodium sulfate, filtered, dried, and column chromatography separation is performed to obtain the purified intermediate P1.

[0024] Preferably, in step (2), the metal salt is selected from any one or combination of copper chloride, zinc chloride, cobalt chloride, zinc acetate, zinc iodide, etc., more preferably any one or combination of zinc chloride, zinc acetate, and zinc iodide.

[0025] Preferably, in step (2), the high-boiling alcohol is selected from any one or combination of n-pentanol, n-butanol, n-hexanol, etc., more preferably n-pentanol.

[0026] Preferably, in step (2), the catalyst is selected from any one or combination of 1,8-diazabicyclo[5.4.0]undec-7-ene and cesium carbonate, more preferably 1,8-diazabicyclo[5.4.0]undec-7-ene.

[0027] Preferably, in step (2), the molar ratio of P1 to the metal salt is 10:1-1:5, more preferably 4:1-1:1.

[0028] Preferably, in step (2), the molar ratio of P1 to the catalyst is 10:1-1:5, more preferably 4:1-1:2.

[0029] Preferably, in step (2), the reaction temperature is 50-250℃, more preferably 100-200℃.

[0030] Preferably, in step (2), the reaction time is 5h-15d, more preferably 8h-7d.

[0031] Preferably, in step (2), the post-processing method is as follows: after stopping the reaction, cool to room temperature, stir the reaction solution and methanol evenly and then filter to obtain a filter cake, and then separate the filter cake by column chromatography to obtain purified phthalocyanine P2; or extract the reaction solution after cooling to room temperature with dichloromethane, wash with saturated brine and dry with anhydrous sodium sulfate, and then filter, dry and separate by column chromatography to obtain purified phthalocyanine P2.

[0032] Compared with the prior art, the beneficial effects of the present invention are:

[0033] (1) The phthalocyanine dye molecules provided by the present invention have high solubility, high transmittance, good thermal stability and light stability;

[0034] (2) The phthalocyanine dye molecules provided by the present invention can be mixed with other colorants to form a green photoresist paste;

[0035] (3) The synthesis method provided by the present invention has a simple route, is easy to scale up and can be used to improve the quality of LCD display. Attached Figure Description

[0036] Figure 1 The compound A1 prepared in Example 1 of this invention 1 H-NMR spectrum;

[0037] Figure 2 The UV-vis absorption spectrum of compound A1 prepared in propylene glycol methyl ether acetate in Example 1 of this invention;

[0038] Figure 3 Thermogravimetric analysis (TGA) of compound A1 prepared in Example 1 of this invention;

[0039] Figure 4 The compound A2 prepared in Example 2 of this invention 1 H-NMR spectrum;

[0040] Figure 5 The compound A3 prepared in Example 3 of this invention 1 H-NMR spectrum. Detailed Implementation

[0041] To better understand the content of this invention, further description is provided below with reference to specific embodiments and accompanying drawings. It should be understood that these embodiments are only for further illustration of the invention and are not intended to limit the scope of the invention. Furthermore, it should be understood that after reading the description of this invention, those skilled in the art may make some non-essential modifications or adjustments to the invention, which still fall within the protection scope of this invention.

[0042] Example 1 (Synthesis of compound A1)

[0043] A method for synthesizing a green phthalocyanine dye with high solubility for photoresist, comprising the following steps:

[0044] (1) A dry and clean 100 mL three-necked flask was taken, and a stirring bar of appropriate size was placed in it; tetrafluorophthalonitrile (6 g, 30.0 mmol, 1.0 eq.), K2CO3 (8.28 g, 59.97 mmol, 2.0 eq.) and DMF (30.0 mL) were added; then, under the protection of a nitrogen atmosphere, a solution of benzoic acid (7.32 g, 59.97 mmol, 2.0 eq.) in DMF (30.0 mL) was added dropwise to the above solvent under ice water bath conditions; after the dropwise addition of the benzoic acid DMF solution was completed, the above reaction system was slowly raised to room temperature, and reacted at room temperature for 12 hours; after the reaction liquid was cooled to room temperature, it was poured into 2000 mL ice water, and dichloromethane was used to extract it; after the dichloromethane was removed by rotary evaporation, the crude product was obtained, and then silica gel column chromatography separation and purification were carried out using petroleum ether / ethyl acetate (5 / 1, v / v) as the developing agent; after the solvent was evaporated, 9.70 g of the intermediate was obtained, with a yield of 72.8%;

[0045] (2) A clean 100 mL single-necked flask was taken, and a stirring bar of appropriate size was placed in it; the intermediate obtained in the previous step (5 g, 12.37 mmol, 3.0 eq.), zinc acetate (0.76 g, 4.12 mmol, 1.0 eq.), 1,8-diazabicyclo[5.4.0]undec-7-ene (1.29 g, 8.24 mmol, 2.0 eq.) and n-pentanol solvent (50 mL) were added; then, under the protection of a nitrogen atmosphere, the above reaction system was slowly raised to 150°C, and reacted overnight at this reaction temperature; the next day, after the reaction was completed, methanol was added to precipitate and filter the crude product; then, silica gel column chromatography separation and purification were carried out using dichloromethane / methanol (45 / 1, v / v) as the developing agent; after the solvent was evaporated, 2.29 g of compound A1 was obtained, with a yield of 44.0%.

[0046] The chemical structural formula of the compound A1 is as follows:

[0047]

[0048] The compound A1 has the following properties: 1 The H-NMR spectrum is shown in Figure 1 The UV-vis absorption spectrum of the compound A1 in propylene glycol methyl ether acetate is shown in Figure 2 The thermogravimetric diagram of the compound A1 is shown in Figure 3 .

[0049] Example 2 (synthesis of compound A2)

[0050] A method for synthesizing a green phthalocyanine dye with high solubility for photoresist, comprising the following steps:

[0051] (1) A dry and clean 100 mL three-necked flask was taken, and a stirring bar of appropriate size was placed in it. Tetrafluorophthalonitrile (6 g, 30.0 mmol, 1.0 eq.), K2CO3 (4.14 g, 30.0 mmol, 1.0 eq.) and DMF (30.0 mL) were added. Then, under the protection of a nitrogen atmosphere, benzoic acid (3.66 g, 30.0 mmol, 1.0 eq.) in DMF (30.0 mL) was added dropwise to the above-mentioned solvent under ice water bath conditions. After the dropwise addition of the benzoic acid in DMF was completed, the above-mentioned reaction system was slowly raised to room temperature, and reacted at room temperature for 12 hours. After the reaction liquid was cooled to room temperature, it was poured into 2000 mL of ice water, and dichloromethane was used to extract it. After dichloromethane was removed by rotary evaporation, the crude product was obtained. Then, petroleum ether / ethyl acetate (5 / 1, v / v) was used as the developing agent for silica gel column chromatography separation and purification. After the solvent was evaporated, 7.84 g of the intermediate was obtained, with a yield of 81.2%.

[0052] (2) A clean 100 mL single-necked flask was taken, and a stirring bar of appropriate size was placed in it. The intermediate obtained in the previous step (5 g, 16.54 mmol, 3.0 eq.), zinc acetate (1.01 g, 5.51 mmol, 1.0 eq.), 1,8-diazabicyclo[5.4.0]undec-7-ene (1.72 g, 11.03 mmol, 2.0 eq.) and n-pentanol solvent (50 mL) were added. Then, under the protection of a nitrogen atmosphere, the above-mentioned reaction system was slowly raised to 150°C, and reacted overnight at this reaction temperature. The next day, after the reaction was completed, methanol was added for precipitation, and the crude product was filtered. Then, dichloromethane / methanol (45 / 1, v / v) was used as the developing agent for silica gel column chromatography separation and purification. After the solvent was evaporated, 2.47 g of compound A2 was obtained, with a yield of 46.9%.

[0053] The chemical structural formula of the compound A2 is as follows:

[0054]

[0055] The 1H-NMR spectrum of the compound A2 is shown in Figure 4 .

[0056] Example 3 (synthesis of compound A3)

[0057] A method for synthesizing a green phthalocyanine dye with high solubility for photoresist, comprising the following steps:

[0058] (1) Take a dry and clean 100 mL three-necked flask, and place a stirring bar of appropriate size; add tetrafluorophthalonitrile (6 g, 30.0 mmol, 1.0 eq.), K2CO3(8.28 g, 59.97 mmol, 2.0 eq.) and DMF (30.0 mL); then, under the protection of nitrogen atmosphere, add a DMF solution (30.0 ml) of 4-methoxybenzoic acid (9.12 g, 59.97 mmol, 2.0 eq.) dropwise into the above solvent under ice-water bath conditions; when the dropwise addition of the DMF solution of 4-methoxybenzoic acid is completed, slowly raise the above reaction system to room temperature, and react at room temperature for 12 hours; after the reaction liquid is cooled to room temperature, pour the reaction liquid into 2000 mL of ice water, extract it with dichloromethane, and after removing dichloromethane by rotary evaporation, obtain the crude product, which is then purified by silica gel column chromatography using petroleum ether / ethyl acetate (5 / 1, v / v) as the developing agent; after the solvent is evaporated, obtain 9.58 g of the intermediate, with a yield of 63.4%;

[0059] (2) Take a clean 100 mL single-necked flask, and place a stirring bar of appropriate size; add the intermediate obtained in the previous step (5 g, 10.77 mmol, 3.0 eq.), zinc acetate (0.66 g, 3.59 mmol, 1.0 eq.), 1,8-diazabicyclo[5.4.0]undec-7-ene (1.12 g, 7.18 mmol, 2.0 eq.), and n-pentanol solvent (50 mL); then, under the protection of nitrogen atmosphere, slowly raise the above reaction system to 150°C, and react overnight at this reaction temperature; the next day, after the reaction is completed, precipitate in methanol, and filter to obtain the crude product, which is then purified by silica gel column chromatography using dichloromethane / methanol (50 / 1, v / v) as the developing agent; after the solvent is evaporated, obtain 2.01 g of compound A3, with a yield of 38.82%.

[0060] The chemical structural formula of the compound A3 is as follows:

[0061]

[0062] The compound A3 has the following properties: 1 The H-NMR spectrum is shown in Figure 5 .

[0063] Comparative Example 1 (synthesis of compound A4)

[0064] A method for synthesizing a green phthalocyanine dye for photoresist, comprising the following steps:

[0065] (1) Take a dry and clean 100 mL three-necked flask, place a suitable size stirrer; add tetrafluorophthalic dinitrile (6 g, 30.0 mmol, 1.0 eq.), K2CO3(8.28 g, 59.97 mmol, 2.0 eq.) and DMF (30.0 mL); then under the protection of nitrogen atmosphere, drop by drop add a solution of phenol (5.64 g, 59.97 mmol, 2.0 eq.) in DMF (30.0 ml) to the above solvent under ice water bath conditions; when the dropwise addition of the phenol DMF solution is completed, slowly raise the above reaction system to room temperature and react at room temperature for 12 hours; after the reaction liquid is cooled to room temperature, pour the reaction liquid into 2000 mL ice water, extract with dichloromethane, and after removing the dichloromethane by rotary evaporation, obtain the crude product, which is then purified by silica gel column chromatography using petroleum ether / ethyl acetate (5 / 1, v / v) as the developing agent. After the solvent is evaporated, 6.96 g of the intermediate is obtained with a yield of 59.8%;

[0066] (2) Take a clean 100 mL single-necked flask, place a suitable size stirrer; add the intermediate obtained in the previous step (5 g, 14.36 mmol, 3.0 eq.), zinc acetate (0.88 g, 4.78 mmol, 1.0 eq.), 1,8-diazabicyclo[5.4.0]undec-7-ene (1.50 g, 9.57 mmol, 2.0 eq.), and add n-pentanol solvent (50 mL); then under the protection of nitrogen atmosphere, slowly raise the above reaction system to 150°C, and react overnight at this reaction temperature; the next day, after the reaction is completed, precipitate with methanol, filter to obtain the crude product, and then purify by silica gel column chromatography using dichloromethane / methanol (45 / 1, v / v) as the developing agent. After the solvent is evaporated, 2.45 g of compound A4 is obtained with a yield of 46.77%.

[0067] The chemical structural formula of the compound A4 is as follows:

[0068]

[0069] Effect experiment example

[0070] I. Determination of the ultraviolet-visible absorption spectrum of phthalocyanine dye molecules

[0071] The phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 were prepared into a 10 μmol / L solution, with propylene glycol methyl ether acetate as the solvent, and the absorption spectrum was tested in a UV-visible spectrophotometer. The molar extinction coefficient of the dye was calculated by the following formula:

[0072] A = εcl

[0073] wherein A is the absorbance 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.

[0074] The transmittance of the dye was calculated by the following formula:

[0075] A = -lgT

[0076] wherein A is the absorbance intensity; and T is the transmittance, %.

[0077] The results of the determination of the UV-visible absorption spectrum of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 are shown in Table 1.

[0078] Table 1 Results of the determination of the UV-visible absorption spectrum of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1

[0079] Dye max / nm ​ ε / 10 4 L / (mol·cm) 530~550 nm transmittance / % Example 1 664 14.0 ＞93 Example 2 652 9.90 ＞91 Example 3 666 12.0 ＞92 Comparative Example 1 694 29.6 ＞92

[0080] As can be seen from Table 1, compared with Comparative Example 1, the maximum absorption wavelength of Examples 1-3 is blue-shifted, and the molar extinction coefficient is also reduced, but the transmittance in the 530-550 nm band is maintained at a high level; the phthalocyanine dye molecule prepared in Example 2 has a slight blue shift compared with Example 1, and the molar extinction coefficient is also slightly lower; the phthalocyanine dye molecule prepared in Example 3 has a maximum absorption wavelength that is not much different from that of Example 1; the transmittance of the phthalocyanine dye molecules prepared in Examples 1-3 in the 530-550 nm band is all higher than 90%, proving that they have high transmittance.

[0081] II. Solubility test of the phthalocyanine dye molecules

[0082] The solubility of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 in propylene glycol methyl ether acetate and N,N-dimethylformamide was tested. A certain amount of dye and organic solvent were weighed, stirred at room temperature for 10 min, and then left to stand for 24 h. The filtrate was filtered three times using a filter membrane, and then dried. The solubility S of the dye was calculated:

[0083] S = 100M S / M L

[0084] wherein M S is the mass of the dye after drying, g; and M L is the mass of the solution, g.

[0085] The results of the solubility test of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 are shown in Table 2.

[0086] Table 2 Results of the solubility test of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1

[0087] Dye [SA 丙二醇甲醚醋酸酯 ]]> [SA N,N-二甲基甲酰胺 ]]> Example 1 ＞10 ＞10 Example 2 ＞10 9.6 Example 3 ＞10 9.8 Comparative Example 1 ＜0.01 1.4

[0088] As shown in Table 2, compared with Comparative Example 1, the phthalocyanine dye molecules prepared in Examples 1-3 all show an order of magnitude increase in solubility in propylene glycol methyl ether acetate and N,N-dimethylformamide, proving that the novel dye molecules provided by the application have excellent solubility, and the phthalocyanine dye molecule prepared in Example 1 has the best solubility in propylene glycol methyl ether acetate and N,N-dimethylformamide.

[0089] III. Thermal stability test of the phthalocyanine dye molecules

[0090] In the process of making color filters, a post-baking process at 200℃ or above 200℃ is required, and the dye molecules are required to have good thermal stability at this temperature. The thermal stability of the synthetic dye was evaluated by thermogravimetry, and the synthetic dye was heated at a temperature increasing rate of 10℃ / min from room temperature to 650℃ under nitrogen protection to determine its thermal decomposition temperature T d .

[0091] The thermal stability test results of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 are shown in Table 3.

[0092] Table 3 Thermal stability test results of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1

[0093] Dye T d (°C) Weight loss rate (230°C) / % Example 1 388.9 0 Example 2 398.1 2.03 Example 3 398.4 0 Comparative Example 1 538.2 0.26

[0094] As shown in Table 3, compared with Comparative Example 1, the phthalocyanine dye molecules prepared in Examples 1-3 have a decrease in T d but are still in the range of 388-400℃, and the weight loss rate at 230℃ is all <5%, indicating that the above dye molecules have good thermal stability.

[0095] The application provides a novel phthalocyanine dye molecule with high solubility, which can be mixed with other colorants to configure a green photoresist color paste. The phthalocyanine dye molecule has a phthalocyanine parent structure, and halogen atoms and alkoxycarbonyl groups are introduced to improve the solubility of the color paste, and the phthalocyanine dye molecule has excellent thermal stability and light stability. The synthesis method provided by the application is simple and easy to scale up, and can be used to improve the quality of LCD display.

[0096] The above description is not a limitation of the application, and the application is not limited to the above examples. Changes, modifications, additions or substitutions made by those skilled in the art within the essential scope of the application shall also fall within the protection scope of the application.

Claims

1. A green phthalocyanine dye for high-solubility photoresists, characterized in that, The chemical structural formula of the green phthalocyanine dye is shown in one of the following formulas: 、 ,and 。 2. The method for synthesizing a green phthalocyanine dye for high-solubility photoresist according to claim 1, characterized in that, Includes the following steps: (1) S N Ar reaction: Under the action of a catalyst, the carboxyl compound S2 attacks the aromatic ring compound S1 to undergo S reaction. N Ar reaction, followed by post-processing to obtain intermediate P1; (2) Preparation of phthalocyanine dye: Using intermediate P1 obtained in step (1), metal salt and high-boiling alcohol as raw materials, the reaction is carried out under the activation conditions of catalyst, and the green phthalocyanine dye P2 is obtained after post-treatment; The synthetic route of the method is as follows: ； The substituents and linking sites in the above chemical formula correspond to the chemical structural formula of the green titanium cyanine dye described in claim 1.

3. The method for synthesizing a green phthalocyanine dye for high-solubility photoresist as described in claim 2, characterized in that, In step (1), the catalyst for the reaction is any one or more of potassium carbonate, sodium carbonate, potassium hydroxide, and sodium hydroxide; the solvent for the reaction is any one or more of N,N-dimethylformamide, acetone, toluene, and xylene.

4. The method for synthesizing a green phthalocyanine dye for high-solubility photoresist as described in claim 2, characterized in that, In step (1), the molar ratio of S1 to S2 is 1:1 to 1:10; the molar ratio of S1 to catalyst is 1:1 to 1:

10.

5. The method for synthesizing a green phthalocyanine dye for high-solubility photoresist as described in claim 2, characterized in that, In step (1), the reaction temperature is -20~120℃ and the reaction time is 1h~7d.

6. The method for synthesizing a green phthalocyanine dye for high-solubility photoresist as described in claim 2, characterized in that, In step (2), the metal salt is any one or more of zinc chloride, zinc acetate, and zinc iodide.

7. The method for synthesizing a green phthalocyanine dye for high-solubility photoresist as described in claim 2, characterized in that, In step (2), the high-boiling alcohol is any one or more of n-pentanol, n-butanol, and n-hexanol.

8. The method for synthesizing a green phthalocyanine dye for high-solubility photoresist as described in claim 2, characterized in that, In step (2), the catalyst is any one or two of 1,8-diazabicyclo[5.4.0]undec-7-ene and cesium carbonate.

9. The method for synthesizing a green phthalocyanine dye for high-solubility photoresist as described in claim 2, characterized in that, In step (2), the molar ratio of P1 to metal salt is 10:1 to 1:5; the molar ratio of P1 to catalyst is 10:1 to 1:

5.

10. The method for synthesizing a green phthalocyanine dye for high-solubility photoresist as described in claim 2, characterized in that, In step (2), the reaction temperature is 50~250℃ and the reaction time is 5h~15d.

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