Green phthalocyanine dye for high-solubility photoresist and synthesis method of green phthalocyanine dye

Abstract

The invention discloses a green phthalocyanine dye for high-solubility photoresist and a synthesis method thereof, the synthesis method comprises the following steps: (1) SNAr reaction: under the action of a catalyst, attacking aromatic rings by using a carboxyl compound to carry out SNAr reaction, and carrying out post-treatment to obtain an intermediate P1; and (2) preparation of phthalocyanine dye: taking the intermediate P1 obtained in the step (1), metal salt and high-boiling-point alcohol as raw materials, carrying out reaction under the activation condition of a catalyst, and carrying out post-treatment to obtain phthalocyanine P2. The invention provides a novel high-solubility phthalocyanine dye molecule, the phthalocyanine dye molecule can be mixed with other coloring agents to prepare green photoresist color paste, phthalocyanine is used as a parent structure, the solubility of the dye is improved by introducing halogen atoms, alkoxycarbonyl and the like, and the phthalocyanine dye molecule has excellent thermal stability and light stability; meanwhile, the synthesis method provided by the invention is simple, is easy for large-scale production, and can be used for improving the display quality of the LCD.

Description

Technical Field

[0001] This invention relates to the field of color paste technology for color photoresists, specifically to a green phthalocyanine dye for high-solubility photoresists and its synthesis method. Background Technology

[0002] Liquid crystal displays (LCDs) have become the mainstream product in the flat panel display market due to their technological advantages such as low voltage, low power consumption, long lifespan, no radiation, and no pollution. The color filter is the core component for realizing the patterns and colors in an LCD. When light passes through the color filter, it is converted into the three primary colors: red, green, and blue. Full-color display is achieved through the mixing of these three primary colors. The color filter consists of a glass substrate, a black matrix, a color layer, an ITO conductive film, and a transparent protective adhesive, with the color layer playing a decisive role in color display.

[0003] Green filter colorants are generally phthalocyanine compounds. Phthalocyanines are aromatic heterocycles composed of four isoindole rings bridged by nitrogen atoms, exhibiting strong π-π electronic interactions, thus possessing rich photophysical / photochemical properties and significant stability. Correspondingly, the strong intermolecular forces also lead to poor dispersibility in organic solvents (such as esters and ketones), easily forming aggregates, which in turn affects the filter's transmittance and color purity, and may even cause uniformity problems in the coating process, resulting in color spots or uneven brightness on the display panel.

[0004] Therefore, researching and developing phthalocyanine dyes with excellent solubility and high photothermal stability to overcome the current shortcomings of low solubility of phthalocyanine dyes is of great significance for the development of a new generation of color filters. Summary of the Invention

[0005] The technical problem to be solved by this invention is to overcome the technical defects of the prior art and provide a high-solubility green phthalocyanine dye for photoresists and its synthesis method. This invention provides a novel high-solubility phthalocyanine dye molecule that can be mixed with other colorants to form a green photoresist paste. It uses phthalocyanine as the parent structure and improves the solubility of the paste by introducing halogen atoms, alkoxycarbonyl groups, etc., and exhibits excellent thermal and photostability. Furthermore, the synthesis method provided by this invention is simple, easy to scale up, and can be used to improve the quality of LCD displays.

[0006] The technical solution adopted by the present invention to solve the above-mentioned technical problems is as follows: A high-solubility green phthalocyanine dye for photoresists, due to the presence of halogen atoms and alkoxycarbonyl groups within the molecule, increases the compatibility of the dye molecule with propylene glycol methyl ether acetate, a commonly used solvent for photoresists, thereby improving the solubility of the dye; the chemical structural formula of the green phthalocyanine dye is shown in General Formula I: ; The symbols in the formula have the following meanings: Mn represents a metal atom, which is not limited and can be exemplified by copper, zinc, cobalt, etc.; R 1 For hydrogen atoms, R 2 For halogen atoms, R 3 For the structure shown in General Formula II, x + y + z = 16, 0 ≤ x ≤ 15, 0 ≤ y ≤ 15, 1 ≤ z ≤ 16, R 4 -R 8 This indicates any substituent, with no restrictions. Examples include hydrogen atom, halogen atom, alkoxy group, alkoxycarbonyl group, aryl group, nitro group, etc.

[0007] The method for synthesizing the green phthalocyanine dye for high-solubility photoresists as described above includes the following steps: (1) S N Ar reaction: Under the action of a catalyst, the carboxyl compound attacks the aromatic ring to carry out 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 phthalocyanine P2 is obtained after post-treatment; The above synthetic route is as follows: ; The symbols in the formula represent the following meanings: Mn represents a metal atom, with no specific requirements; examples include copper, zinc, and cobalt. R 4 -R 8 This indicates any substituent, with no restrictions; examples include hydrogen atom, halogen atom, alkoxy group, alkoxycarbonyl group, aryl group, nitro group, etc.; R 9 -R 12 They can be represented independently as H, F, Cl, NO2, etc.

[0008] Preferably, in step (1), the catalyst used in the reaction can be selected from any one or a combination of alkaline substances such as potassium carbonate, sodium carbonate, potassium hydroxide, and sodium hydroxide, and more preferably from any one or a combination of potassium carbonate and sodium carbonate.

[0009] Preferably, in step (1), the organic solvent used in the reaction can be selected from any one or a combination of N,N-dimethylformamide, acetone, toluene, xylene, etc., and more preferably from any one or a combination of N,N-dimethylformamide and acetone.

[0010] Preferably, in step (1), the molar ratio of S1 to S2 is 1:1 to 1:10, more preferably 1:1 to 1:5.

[0011] Preferably, in step (1), the molar ratio of S1 to catalyst is 1:1 to 1:10, more preferably 1:1 to 1:5.

[0012] Preferably, in step (1), the reaction temperature is -20~120℃, more preferably 0~80℃.

[0013] Preferably, in step (1), the reaction time is 1h to 7d, more preferably 8h to 2d.

[0014] Preferably, in step (1), the post-processing method is as follows: after stopping the reaction, cool to room temperature, stir the cooling liquid and ice water evenly and then filter to obtain a filter cake, and then separate the filter cake by column chromatography to obtain the purified intermediate P1; 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 the purified intermediate P1.

[0015] Preferably, in step (2), the metal salt is selected from any one or a combination of copper chloride, zinc chloride, cobalt chloride, zinc acetate, zinc iodide, etc., and more preferably from any one or a combination of zinc chloride, zinc acetate, zinc iodide, etc.

[0016] Preferably, in step (2), the high-boiling alcohol is selected from any one or a combination of n-pentanol, n-butanol, n-hexanol, etc., and more preferably n-pentanol.

[0017] Preferably, in step (2), the catalyst is selected from any one or a 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.

[0018] Preferably, in step (2), the molar ratio of P1 to the metal salt is 10:1 to 1:5, more preferably 4:1 to 1:1.

[0019] Preferably, in step (2), the molar ratio of P1 to the catalyst is 10:1 to 1:5, more preferably 4:1 to 1:2.

[0020] Preferably, in step (2), the reaction temperature is 50~250℃, more preferably 100~200℃.

[0021] Preferably, in step (2), the reaction time is 5h~15d, more preferably 8h~7d.

[0022] 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.

[0023] Compared with the prior art, the present invention has the following beneficial effects: (1) The phthalocyanine dye molecules provided by the present invention have high solubility, high transmittance, good thermal stability and light stability; (2) The phthalocyanine dye molecules provided by the present invention can be mixed with other colorants to form a green photoresist paste; (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

[0024] Figure 1 The compound A1 prepared in Example 1 of this invention 1 H-NMR spectrum; Figure 2 The UV-vis absorption spectrum of compound A1 prepared in propylene glycol methyl ether acetate in Example 1 of this invention; Figure 3 Thermogravimetric analysis (TGA) of compound A1 prepared in Example 1 of this invention; Figure 4 The compound A2 prepared in Example 2 of this invention 1 H-NMR spectrum; Figure 5 The compound A3 prepared in Example 3 of this invention 1 H-NMR spectrum. Detailed Implementation

[0025] 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.

[0026] Example 1 (Synthesis of compound A1) A method for synthesizing a green phthalocyanine dye for high-solubility photoresists, comprising the following steps: (1) Take a dry and clean 100 mL three-necked flask and place a stir 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 a nitrogen atmosphere and in an ice-water bath, add benzoic acid (7.32 g, 59.97 mmol, 2.0 eq.) in DMF solution (30.0 mL) dropwise to the above solvent; after the DMF solution of benzoic acid has been added, slowly raise the above reaction system to room temperature and react at room temperature for 12 hours; after the reaction solution cools to room temperature, pour the reaction solution into 2000 mL of ice water, extract it with dichloromethane, remove the dichloromethane by rotary evaporation to obtain the crude product, and then use petroleum ether / ethyl acetate (5 / 1, The intermediate was purified by silica gel column chromatography using (v / v) as the developing solvent. After evaporation of the solvent, 9.70 g of the intermediate was obtained, with a yield of 72.8%. (2) Take a clean 100 mL single-necked flask and place a stir bar of appropriate size; add 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 add n-pentanol solvent (50 mL); then, under a nitrogen-protected 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, methanol is precipitated and filtered to obtain crude product, which is then purified by silica gel column chromatography using dichloromethane / methanol (45 / 1, v / v) as the developing solvent. After evaporating the solvent to dryness, compound A1 2.29 g is obtained, with a yield of 44.0%.

[0027] The chemical structural formula of compound A1 is as follows:

[0028] The compound A1 1 The H-NMR spectrum is shown below. Figure 1 The UV-vis absorption spectrum of compound A1 in propylene glycol methyl ether acetate is shown in [reference needed]. Figure 2 The thermogravimetric diagram of compound A1 is shown below. Figure 3 .

[0029] Example 2 (Synthesis of compound A2) A method for synthesizing a green phthalocyanine dye for high-solubility photoresists, comprising the following steps: (1) Take a dry and clean 100 mL three-necked flask and place a stir bar of appropriate size; add tetrafluorophthalonitrile (6 g, 30.0 mmol, 1.0 eq.), K2CO3 (4.14 g, 30.0 mmol, 1.0 eq.) and DMF (30.0 mL); then, under a nitrogen atmosphere and in an ice-water bath, add dropwise a DMF solution (30.0 mL) of benzoic acid (3.66 g, 30.0 mmol, 1.0 eq.) to the above solvent; after the DMF solution of benzoic acid has been added, slowly raise the above reaction system to room temperature and react at room temperature for 12 hours; after the reaction solution cools to room temperature, pour the reaction solution into 2000 mL of ice water, extract it with dichloromethane, remove the dichloromethane by rotary evaporation to obtain the crude product, and then use petroleum ether / ethyl acetate (5 / 1, The intermediate was purified by silica gel column chromatography using (v / v) as the developing solvent. After evaporation of the solvent, 7.84 g of the intermediate was obtained, with a yield of 81.2%. (2) Take a clean 100 mL single-necked flask and place a stir bar of appropriate size; add 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 add n-pentanol solvent (50 mL); then, under a nitrogen-protected 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, methanol is precipitated and filtered to obtain the crude product, which is then purified by silica gel column chromatography using dichloromethane / methanol (45 / 1, v / v) as the developing solvent. After evaporating the solvent to dryness, compound A2 2.47 g is obtained, with a yield of 46.9%.

[0030] The chemical structural formula of compound A2 is as follows:

[0031] The 1H-NMR spectrum of compound A2 is shown below. Figure 4 .

[0032] Example 3 (Synthesis of compound A3) A method for synthesizing a green phthalocyanine dye for high-solubility photoresists, comprising the following steps: (1) Take a dry and clean 100 mL three-necked flask and place a stir 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 a nitrogen atmosphere and in an ice-water bath, add dropwise a DMF solution (30.0 mL) of 4-methoxybenzoic acid (9.12 g, 59.97 mmol, 2.0 eq.) to the above solvent; after the DMF solution of 4-methoxybenzoic acid has been added, slowly raise the above reaction system to room temperature and react at room temperature for 12 hours; after the reaction solution cools to room temperature, pour the reaction solution into 2000 mL of ice water, extract it with dichloromethane, remove the dichloromethane by rotary evaporation to obtain the crude product, and then use petroleum ether / ethyl acetate (5 / 1, The intermediate was purified by silica gel column chromatography using (v / v) as the developing solvent. After evaporating the solvent to dryness, 9.58 g of the intermediate was obtained, with a yield of 63.4%. (2) Take a clean 100 mL single-necked flask and place a stir 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 add n-pentanol solvent (50 mL); then, under a nitrogen-protected 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, methanol is precipitated and filtered to obtain crude product, which is then purified by silica gel column chromatography using dichloromethane / methanol (50 / 1, v / v) as the developing solvent. After evaporating the solvent to dryness, compound A3 2.01 g is obtained, with a yield of 38.82%.

[0033] The chemical structural formula of compound A3 is as follows:

[0034] The compound A3 1 See the H-NMR spectrum. Figure 5 .

[0035] Comparative Example 1 (Synthesis of Compound A4) A method for synthesizing a green phthalocyanine dye for photoresist, comprising the following steps: (1) Take a dry and clean 100 mL three-necked flask and place a stir 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 a nitrogen atmosphere and in an ice-water bath, add dropwise a DMF solution (30.0 mL) of phenol (5.64 g, 59.97 mmol, 2.0 eq.) to the above solvent; after the DMF solution of phenol has been added, slowly raise the above reaction system to room temperature and react at room temperature for 12 hours; after the reaction solution cools to room temperature, pour the reaction solution into 2000 mL of ice water, extract it with dichloromethane, remove the dichloromethane by rotary evaporation to obtain the crude product, and then use petroleum ether / ethyl acetate (5 / 1, The intermediate was purified by silica gel column chromatography using (v / v) as the developing solvent. After evaporation of the solvent, 6.96 g of the intermediate was obtained, with a yield of 59.8%. (2) Take a clean 100 mL single-necked flask and place a stir bar of appropriate size; 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 a nitrogen-protected 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, methanol is precipitated and filtered to obtain crude product, which is then purified by silica gel column chromatography using dichloromethane / methanol (45 / 1, v / v) as the developing solvent. After evaporating the solvent to dryness, compound A4 2.45 g is obtained, with a yield of 46.77%.

[0036] The chemical structural formula of compound A4 is as follows:

[0037] Effect Experiment Example I. Determination of UV-Vis Absorption Spectroscopy of Phthalocyanine Dye Molecules The phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 were formulated into 10 μmol / L solutions using propylene glycol methyl ether acetate as the solvent, and their absorption spectra were measured using a UV-Vis spectrophotometer. The molar extinction coefficient of the dye was calculated using the following formula: Α = εcl In the formula, 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.

[0038] The dye transmittance is calculated using the following formula: A=-lgT In the formula, A is the light absorption intensity; T is the transmittance.

[0039] The UV-Vis absorption spectra of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 are shown in Table 1.

[0040] Table 1. UV-Vis absorption spectra of phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 dye <![CDATA[λ max / nm]]> <![CDATA[ε / 10 4 L / (mol cm)]]> 530~550nm 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 As shown in Table 1, compared with Comparative Example 1, the maximum absorption wavelength of Examples 1-3 showed a blue shift, and the molar absorptivity also decreased, but the transmittance in the 530-550 nm band remained at a high level. The phthalocyanine dye molecules prepared in Example 2 showed a slight blue shift compared to Example 1, and the molar absorptivity was also slightly lower. The phthalocyanine dye molecules prepared in Example 3 had a maximum absorption wavelength that was not much different from that of Example 1. The phthalocyanine dye molecules prepared in Examples 1-3 all had a transmittance of over 90% in the 530-550 nm band, proving that they have high transmittance.

[0041] II. Solubility Test of Phthalocyanine Dye Molecules The solubility of 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 allowed to stand for 24 h. The mixture was filtered three times using a filter membrane, and the filtrate was dried. The solubility S of the dye was calculated. S = 100M S / M L In the formula, M S This refers to the mass of the dye after drying, in grams (g); in milliliters (M). L This is the mass of the solution, in grams (g).

[0042] The solubility test results of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 are shown in Table 2.

[0043] Table 2. Solubility test results of phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 dye <![CDATA[S 丙二醇甲醚醋酸酯 ]]> <![CDATA[S 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 As shown in Table 2, compared with Comparative Example 1, the phthalocyanine dye molecules prepared in Examples 1-3 all showed an order of magnitude increase in propylene glycol methyl ether acetate and N,N-dimethylformamide, proving that the novel dye molecules provided by the present invention have excellent solubility. Among them, the phthalocyanine dye molecules prepared in Example 1 have the best solubility in propylene glycol methyl ether acetate and N,N-dimethylformamide.

[0044] III. Thermal stability test of phthalocyanine dye molecules The fabrication of color filters involves a post-baking process at 200℃ or higher, as industrial applications require dye molecules to exhibit good thermal stability at this temperature. Thermogravimetric analysis (TGA) is used to evaluate the thermal stability of synthetic dyes. Under nitrogen protection, the synthetic dyes are heated from room temperature to 650℃ at a rate of 10℃ / min to determine their thermal decomposition temperature T. d .

[0045] The thermal stability test results of the phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 are shown in Table 3.

[0046] Table 3. Thermal stability test results of phthalocyanine dye molecules prepared in Examples 1-3 and Comparative Example 1 dye <![CDATA[T d (℃)]]> Weight loss rate (230℃) / % Example 1 388.9 0 Example 2 398.1 2.03 Example 3 398.4 0 Comparative Example 1 538.2 0.26 As shown in Table 3, compared with Comparative Example 1, the phthalocyanine dye molecules T prepared in Examples 1-3... d The temperature decreased but remained within the range of 388~400℃, and the weight loss rate at 230℃ was less than 5%, indicating that the above dye molecules have good thermal stability.

[0047] This invention provides a novel high-solubility phthalocyanine dye molecule that can be mixed with other colorants to form a green photoresist paste. It uses phthalocyanine as the parent structure and improves the solubility of the paste by introducing halogen atoms, alkoxycarbonyl groups, etc. It also has excellent thermal and light stability. At the same time, the synthesis method provided by this invention is simple, easy to scale up, and can be used to improve the quality of LCD displays.

[0048] The foregoing description is not intended to limit the invention, nor is the invention limited to the examples given. Any changes, modifications, additions, or substitutions made by those skilled in the art within the scope of the invention should also be considered within the protection scope of the invention.

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 general formula I: ； The symbols in the formula represent the following meanings: Mn is a metal atom, R 1 For hydrogen atoms, R 2 For halogen atoms, R 3 For the structure shown in General Formula II, x + y + z = 16, 0 ≤ x ≤ 15, 0 ≤ y ≤ 15, 1 ≤ z ≤ 16, R 4 -R 8 It can be any substituent.

2. A method for synthesizing a green phthalocyanine dye for high-solubility photoresists, characterized in that, The steps include: (1) S N Ar reaction: Under the action of a catalyst, the carboxyl compound attacks the aromatic ring to carry out 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 phthalocyanine P2 is obtained after post-treatment; The above synthetic route is as follows: ； The symbols in the formula represent the following meanings: Mn is a metal atom, R 4 -R 8 For any substituent, R 9 -R 12 Each of these can be represented independently as H, F, Cl, and NO2.

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 copper chloride, zinc chloride, cobalt 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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