A diazonium naphthoquinone type photosensitive compound and its application in photoresist preparation

Abstract

The present application relates to a photosensitive compound for G / I line photoresist, which is composed of polycarbonyl enol compound and diazonaphthoquinone sulfonyl group. The present application also provides a synthesis method of the photosensitive compound, by which a diazonaphthoquinone sulfonate photosensitive compound with excellent performance can be prepared, and the component ratio of the photosensitive compound can be adjusted arbitrarily. The present application also provides the application of the photosensitive compound in photoresist configuration, and the configured photoresist has good performance.

Description

Technical Field

[0001] This invention relates to the field of photosensitizer technology, and more specifically to a photosensitive compound, preparation method, and photoresist composition suitable for i-line photoresists. Background Technology

[0002] Positive photoresists composed of diazononaphthoquinone (DNQ) photoinitiators and phenolic resins are among the most typical photoresists used in G / I line lithography processes. As early as 1942, Suess reported the Wolff rearrangement mechanism of DNQ: under illumination, the diazonium bond of DNQ decomposes, releasing N2 and generating 1-indenecarboxylic acid. Its excellent photosensitivity to 436 and 365 nm wavelengths, along with its unique structural variations, makes DNQ an ideal raw material for G / I line photoinitiators.

[0003] However, for DNQ-type photoinitiators to be applied in the field of semiconductor photoresists, they also need to be compatible with polymer resins. DNQ molecules form intermolecular hydrogen bonds with the phenolic hydroxyl groups on the phenolic resin, causing the DNQ-type photoinitiator to couple onto the molecular chain of the phenolic polymer, reducing its solubility in certain solvents. When DNQ is exposed to ultraviolet light, its structure changes, the intermolecular hydrogen bonds are broken, and the dissociation of the DNQ-type photoinitiator leads to an increase in the solubility of the polymer molecules. Therefore, the exposed photoresist can be dissolved and removed, thus completing the transfer of the photolithographic pattern.

[0004] The photosensitivity and resin solubility inhibition properties of DNQ-type photoinitiators are mainly influenced by the type of graft. Combining with different grafts can regulate the number and relative positions of DNQ groups per unit photoinitiator. Increasing the number of DNQ groups enhances the photosensitivity contrast of the photoinitiator, while the distance between the groups affects its ability to inhibit polymer resin solubility. Therefore, synthesizing and designing effective graft structures is key to enhancing the performance of diazonoquinone photoinitiators. Summary of the Invention

[0005] In view of the above reasons, the present invention provides a diazononaphthoquinone-type photosensitive compound, its preparation method, and its application in G / I photoresist preparation. This diazononaphthoquinone-type photosensitive compound can be used to prepare G / I line photoresists, and the resulting photoresists exhibit good performance.

[0006] To achieve the above objectives, according to the first part of the present invention, a diazononaphthoquinone sulfonate is provided, the diazononaphthoquinone sulfonate having the structure shown in Formula I:

[0007]

[0008] In each of the following, X represents N, C, Si, benzene ring, and aromatic heterocycle, and R represents hydrogen, halogen, C1-C18 alkyl branched or straight chain, aromatic hydrocarbon, C2-C10 unsaturated hydrocarbon group, and C3-C12 cycloalkyl group. k represents any integer between 1 and 4, n represents an integer between 0 and 2, and m represents an integer between 2 and 4. The multiple substituents on X are uniformly and symmetrically distributed.

[0009] Furthermore, the diazonoquinone sulfonate is selected from at least one of the following structural compounds:

[0010]

[0011] According to a second part of the present invention, a method for preparing diazonoquinone sulfonate is also provided, the method comprising:

[0012] Step A1: Mix the polycarbonyl enol compound and diazonoquinone sulfonyl chloride in an organic solvent, and react them by adding an alkaline activator to obtain the diazonoquinone sulfonate product system;

[0013] Step A2: Add hydrochloric acid to the diazonium naphthoquinone sulfonate product system obtained in A1 and filter to remove inorganic salt byproducts. Then add a large amount of water to the organic phase to precipitate the diazonium naphthoquinone sulfonate product.

[0014] Step A3: Purify the diazonoquinone sulfonate product to obtain a diazonoquinone-type photoinitiator product.

[0015] Further, in the above steps, the reaction is carried out under an inert gas protective atmosphere, the reaction temperature is 20–60°C, preferably 25–40°C, and the reaction time is 0.5–6 h, preferably 1–3 h; preferably, the alkaline catalyst includes at least one of triethylamine, tripropylamine, ethylenediamine, pyridine, N,N-dimethylaniline, tetramethylammonium hydroxide, sodium methoxide, sodium ethoxide, lithium diisopropylamino, sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium bicarbonate, potassium hydroxide, ammonium hydroxide, and sodium hydride, preferably at least one of triethylamine, pyridine, and sodium bicarbonate. The organic solvent includes at least one of dichloromethane, tetrahydrofuran, 1,4-dioxane, N,N-dimethylformamide, toluene, acetonitrile, and methanol.

[0016] For those skilled in the art, it is unavoidable to perform impurity removal treatment on the diazonaquinone sulfonate product system. This impurity removal treatment is aimed at removing impurities such as unreacted products and reaction byproducts. The impurity removal treatment includes, as is well known in the art, adding the obtained diazonaquinone sulfonate product system to a hydrochloric acid solution (1.0-5.0 wt%), followed by filtration to remove inorganic salt byproducts, then adding a large amount of water to the organic phase to precipitate the diazonaquinone sulfonate product, and finally filtering and drying to obtain the diazonaquinone-type photoinitiator product.

[0017] Furthermore, the polycarbonyl enol compound has the structure shown in Formula II:

[0018]

[0019] Where X represents N, C, Si, benzene ring, and aromatic heterocycle, R represents hydrogen, halogen, C1-C18 alkyl branched or straight chain, aromatic hydrocarbon, C2-C10 unsaturated hydrocarbon group, and C3-C12 cycloalkyl, n represents an integer between 0 and 2, and m represents an integer between 2 and 4.

[0020] Furthermore, the polycarbonyl enol compound is selected from at least one of the following structural compounds:

[0021]

[0022] Furthermore, the polycarbonyl enol compound is prepared by the following method:

[0023]

[0024] Step A1: Acetyl compounds are synthesized from raw material a through an acylation reaction;

[0025] Step A2: Synthesis of carboxylic acid compounds via the Willgerodt-Kindler reaction;

[0026] Step A3: Prepare the Vilsmeier-Haack-Arnold reagent by adding carboxylic acid compounds to the Vilsmeier-Haack-Arnold reagent to synthesize onium salt compounds;

[0027] Step A4: Hydrolyze the onium salt compound to obtain a polycarbonyl enol compound;

[0028] Where X represents N, C, Si, benzene ring, and aromatic heterocycle, R represents hydrogen, halogen, C1-C18 alkyl branched or straight chain, aromatic hydrocarbon, C2-C10 unsaturated hydrocarbon group, and C3-C12 cycloalkyl, n represents an integer between 0 and 2, and m represents an integer between 2 and 4.

[0029] Further, in step A1, the molar ratio of raw material a to acetyl chloride is 1:3-8, more preferably 1:4-6; the reaction is carried out under anhydrous conditions and protected by an inert gas, the reaction temperature is 25-55℃, preferably 30-45℃, and the reaction time is 12-48h, preferably 12-18h; the solvent includes at least one of dichloromethane, chloroform, carbon tetrachloride, and carbon disulfide.

[0030] Further, in step A2, the molar ratio of acetyl compound (raw material b): sulfur powder: sodium hydroxide is 1:6-16:6-16, more preferably 1:6-12:6-12; the reaction temperature is 90-160℃, more preferably 100-140℃, and the reaction time is 24-36h, more preferably 30-36h.

[0031] Further, in step A3, the molar ratio of carboxylic acid compound (raw material c): DMF: phosphorus oxychloride is 1:100-200:10-50, more preferably 1:120-160:30-50; the reaction is carried out under nitrogen protection at a temperature of 90-120 degrees Celsius, more preferably 100-105 degrees Celsius; the reaction time is preferably 36-48 hours.

[0032] Further, in step A4, the reaction solvent is methanol, and the molar ratio of raw material d to sodium methoxide is 1:10-30, more preferably 1:20-25; the reaction is carried out under nitrogen protection, the reaction temperature is preferably 35-45℃, and the reaction time is preferably 8-12h.

[0033] According to the third part of the present invention, an application of the diazonaphthoquinone sulfonate as described above in a photoresist formulation is also provided, wherein the photoresist includes a photosensitizer, said photosensitizer being any of the diazonaphthoquinone sulfonates provided in the first part above or a diazonaphthoquinone sulfonate obtained according to any of the preparation methods provided in the second part above.

[0034] The photoresist also includes a resin, which is a phenolic resin with a weight-average molecular weight (Mw) of 2000 to 40000.

[0035] Furthermore, the diazonaphthoquinone sulfonate accounts for 0.5-5.0% of the mass of the photoresist composition.

[0036] The present invention provides a solution using the diazonaphthoquinone sulfonate and its preparation method. When this diazonaphthoquinone sulfonate photosensitive compound is applied to a photoresist composition, the resulting photoresist exhibits high resolution and good performance. Detailed Implementation

[0037] The technical solution of the present invention will be further explained and described below with reference to specific embodiments. It is worth noting that the following embodiments are only preferred embodiments of the present invention and should not be construed as limiting the present invention. The scope of protection of the present invention should be determined by the contents of the claims. Modifications and substitutions made by those skilled in the art to the technical solution of the present invention without creative effort all fall within the scope of protection of the present invention.

[0038] In a first typical embodiment of this application, a diazononaphthoquinone sulfonate is provided, the diazononaphthoquinone sulfonate having the structure shown in Formula I:

[0039]

[0040] In each of the following, X represents N, C, Si, benzene ring, and aromatic heterocycle, and R represents hydrogen, halogen, C1-C18 alkyl branched or straight chain, aromatic hydrocarbon, C2-C10 unsaturated hydrocarbon group, and C3-C12 cycloalkyl group. k represents any integer between 1 and 4, n represents an integer between 0 and 2, and m represents an integer between 2 and 4. The multiple substituents on X are uniformly and symmetrically distributed.

[0041] Furthermore, the diazonoquinone sulfonate is selected from at least one of the following structural compounds:

[0042]

[0043] According to a second part of the present invention, a method for preparing diazonoquinone sulfonate is also provided, the method comprising:

[0044] Step A1: Mix the polycarbonyl enol compound and diazonoquinone sulfonyl chloride in an organic solvent, and react them by adding an alkaline activator to obtain the diazonoquinone sulfonate product system;

[0045] Step A2: Add hydrochloric acid to the diazonium naphthoquinone sulfonate product system obtained in A1 and filter to remove inorganic salt byproducts. Then add a large amount of water to the organic phase to precipitate the diazonium naphthoquinone sulfonate product.

[0046] Step A3: Purify the diazonoquinone sulfonate product to obtain a diazonoquinone-type photoinitiator product.

[0047] Furthermore, the polycarbonyl enol compound is selected from at least one of the following structural compounds:

[0048]

[0049] The diazonoquinone sulfonyl chloride represents at least one of the following structural compounds:

[0050]

[0051] The preparation method of diazonaphthoquinone sulfonate provided in this application has a reasonable process route, simple and easy-to-operate synthesis conditions, is economical and environmentally friendly, and is easy to realize large-scale industrial production.

[0052] To further improve the yield and preparation efficiency of polycarbonyl enol compounds, while saving production energy and costs, the following optimizations were made to the various synthetic conditions involved in this synthetic route:

[0053] Further, in step A1, the reaction is carried out under an inert gas protective atmosphere, the reaction temperature is 20–60°C, preferably 25–40°C, and the reaction time is 0.5–6 h, preferably 1–3 h; preferably, the alkaline catalyst includes at least one of triethylamine, tripropylamine, ethylenediamine, pyridine, N,N-dimethylaniline, tetramethylammonium hydroxide, sodium methoxide, sodium ethoxide, lithium diisopropylamino, sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium bicarbonate, potassium hydroxide, ammonium hydroxide, and sodium hydride, preferably at least one of triethylamine, pyridine, and sodium bicarbonate.

[0054] To further improve purification efficiency, it is preferable that in step A3 above, purification includes at least one of dissolution and precipitation, washing, recrystallization, and vacuum drying.

[0055] To further improve the efficiency of precipitation after dissolution, 1,4-dioxane is preferred as a good solvent, ultrapure water is preferred as a poor solvent, and the ratio of 1,4-dioxane to ultrapure water is preferably 20:80.

[0056] To further improve vacuum drying efficiency, a negative pressure of 10–500 mbar and a temperature of 40–50 °C are preferred.

[0057] In some embodiments of this application, diazonoquinone sulfonate was prepared according to the following steps:

[0058] (1) Under an inert gas protective atmosphere, the polycarbonyl enol compound and DNQ are mixed evenly in an organic solvent;

[0059] (2) Add the alkaline activator slowly at room temperature, heat to the reaction temperature, and then allow the reaction to mature for a period of time.

[0060] (3) After the reaction in step (2) is completed, the liquid is slowly added to dilute hydrochloric acid (mass concentration 1.0% to 2.5%), stirred to precipitate solid, filtered to obtain diazonoquinone sulfonate solution, and then slowly added to ultrapure water to precipitate diazonoquinone sulfonate solid.

[0061] (4) The solid diazonoquinone sulfonate obtained in step (3) is washed three times with pure water and dried under reduced pressure to obtain diazonoquinone sulfonate.

[0062] According to the third part of the present invention, the use of the diazonaphthoquinone sulfonate as described in claim 1 in a photoresist composition is also provided, the photoresist composition comprising a resin and a photosensitizer, the photosensitizer being any of the diazonaphthoquinone sulfonates provided in the first part above or a diazonaphthoquinone sulfonate obtained according to any of the preparation methods provided in the second part above.

[0063] Furthermore, the mass percentage of diazonaphthoquinone sulfonate in the photoresist composition is 0.5-5.0%;

[0064] Furthermore, the preferred resin is phenolic resin, with a weight-average molecular weight (Mw) of 2000–40000.

[0065] In some embodiments of this application, during the preparation of photoresist using the above-mentioned photoresist composition, phenolic resin and photosensitizer are dispersed in propylene glycol methyl ether acetate to facilitate the preparation of a photoresist with stable performance.

[0066] The present invention provides a solution using the diazonaphthoquinone sulfonate and its preparation method. When this diazonaphthoquinone sulfonate photosensitive compound is applied to a photoresist composition, the resulting photoresist exhibits high resolution and good performance.

[0067] The beneficial effects of this application will be further illustrated below with reference to the embodiments.

[0068] Example 1

[0069] This embodiment provides a method for preparing diazonoquinone sulfonate P5-1, the reaction formula of which is shown below, and the specific steps include:

[0070]

[0071] Under an inert gas atmosphere, 15g of raw material S5 and 9g of diazonoquinone compound D1 were dissolved in 250ml of 1,4-dioxane. The reaction temperature was maintained at 30-35℃. Then, 10g of triethylamine was slowly added dropwise over 1 hour. The mixture was allowed to mature for another hour. Then, 1.0-1.5wt% dilute hydrochloric acid was slowly added. After filtration, the filtrate was added to 800ml of ultrapure water. After filtration, the filter cake was filtered and dried to obtain a pale yellow solid product P5-1. HPLC analysis showed that the effective ester content was 99.2% and the grafting rate was approximately 89.2%.

[0072] Example 2

[0073] This embodiment provides a method for preparing diazonoquinone sulfonate P10-1, the reaction formula of which is shown below, and the specific steps include:

[0074]

[0075] The preparation method in Example 2 differs from that in Example 1 in that raw material S5 is replaced with 15g of raw material S10, and 16g of diazonoquinone D1 is used, while other conditions remain unchanged. A pale yellow solid product, P10-1, was obtained. HPLC analysis showed that the effective ester content was 99.4%, and the grafting rate was approximately 81.7%.

[0076] Example 3

[0077] This embodiment provides a method for preparing diazonoquinone sulfonate P15-1, the reaction formula of which is shown below, and the specific steps include:

[0078]

[0079] The preparation method in Example 3 differs from that in Example 1 in that raw material S5 is replaced with 15g of raw material S15, and 11g of diazonoquinone D1 is used, while other conditions remain unchanged. A pale yellow solid product, P15-1, was obtained. HPLC analysis showed that the effective ester content was 99.2%, and the grafting rate was approximately 87.4%.

[0080] Example 4

[0081] This embodiment provides a method for preparing diazonoquinone sulfonate P4-2, the reaction formula of which is shown below, and the specific steps include:

[0082]

[0083] The preparation method in Example 4 differs from that in Example 1 in that raw material S5 is replaced with 15g of raw material S4, and diazonaquinone D1 is replaced with 15g of diazonaquinone D2, while other conditions remain unchanged. A pale yellow solid product P4-2 was obtained. HPLC analysis showed that the effective ester content was 98.7%, and the grafting rate was approximately 83.7%.

[0084] Example 5

[0085] This embodiment provides a method for preparing diazonaphthoquinone sulfonate P2-2, and the reaction formula for its preparation is as follows:

[0086]

[0087] The preparation method in Example 5 differs from that in Example 1 in that raw material S5 is replaced with 15g of raw material S2, and 11g of diazonoquinone D2 is used, while other conditions remain unchanged. A pale yellow solid product P2-2 is obtained. HPLC analysis shows that the effective ester content is 99.4%, and the grafting rate is approximately 85.7%.

[0088] Example 6

[0089] This embodiment provides a method for preparing diazonoquinone sulfonate P3-2, and the reaction formula for its preparation is as follows:

[0090]

[0091] The difference between the preparation method in Application Example 6 and Application Example 1 is that raw material S5 was replaced with 15g of raw material S3, and 17g of diazonoquinone D2 was used, while other conditions remained unchanged. A pale yellow solid product P3-2 was obtained, and HPLC analysis showed that the effective ester content was 98.6% and the grafting rate was 84.9%.

[0092] Example 7

[0093] This embodiment provides a method for preparing diazonoquinone sulfonate P7-3, and the reaction formula for its preparation is as follows:

[0094]

[0095] The difference between the preparation method in Application Example 7 and Application Example 1 is that raw material S5 was replaced with 15g of raw material S7, and 8g of diazonoquinone D3 was used, while other conditions remained unchanged. A pale yellow solid product P7-3 was obtained, and HPLC analysis showed that the effective ester content was 99.1% and the grafting rate was 87.9%.

[0096] Example 8

[0097] This embodiment provides a method for preparing diazonoquinone sulfonate P11-3, and the reaction formula for its preparation is as follows:

[0098]

[0099] The preparation method in Example 4 differs from that in Example 1 in that raw material S5 is replaced with 15g of raw material S11, and 13g of diazonoquinone D3 is used, while other conditions remain unchanged. A pale yellow solid product S11-3 is obtained, and HPLC analysis shows that the effective ester content is 98.9%, and the grafting rate is 84.5%.

[0100] Example 9

[0101] This embodiment provides a method for preparing diazonoquinone sulfonate S13-3, and the reaction formula for its preparation is as follows:

[0102]

[0103] The preparation method in Example 9 differs from that in Example 1 in that raw material S5 is replaced with 15.0 g of raw material S13, and diazonoquinone compound D1 is replaced with 16 g of D3, while other conditions remain unchanged. A pale yellow solid product S13-3 was obtained, and HPLC analysis showed that the effective ester content was 99.3% and the grafting rate was 89.3%.

[0104] Comparative Example 1

[0105] The solubility of compound S19 (2,3,4,4'-tetrahydroxybenzophenone-2,1,5-diazonaphthoquinone sulfonate, a commercially available product) and the diazonaphthoquinone sulfonates P5-1, P10-1, P15-1, P4-2, P2-2, P3-2, P7-3, P11-3, and P13-3 provided in Examples 1-9 in propylene glycol methyl ether acetate were tested, and the results are shown in Table 1 below.

[0106] The solubility test method is as follows: At room temperature (20±0.5℃), 5 ml of propylene glycol methyl ether acetate is used as the solvent. The sample is added to the solvent while stirring until an insoluble sample solid appears. Stirring continues for 10 minutes until the sample no longer dissolves. At this point, about 2 ml of the supernatant is pipetted through a 25 μm filter and added dropwise to an evaporating dish. The weight is recorded as m1. Then, the evaporating dish is placed in a vacuum desiccator at 40℃ to evaporate the solvent, and the weight is recorded as m2.

[0107] Table 1

[0108] sample Solubility (wt%) P5-1 3.89 P10-1 3.56 P15-1 3.25 P4-2 2.23 P2-2 2.87 P3-2 3.14 P7-3 2.98 P11-3 3.12 P13-3 3.26 S19 1.98

[0109] As can be seen from Table 1, all the novel diazononaphthoquinone sulfonate photosensitive compounds of the present invention, like the widely used 2,3,4,4'-tetrahydroxybenzophenone-2,1,5-diazonaphthoquinone sulfonate S19, have good solubility in propylene glycol methyl ether acetate solvent. Among them, the novel diazononaphthoquinone sulfonate photosensitive compounds P5-1, P10-1, P15-1, P4-2, P2-2, P3-2, P7-3, P11-3, and P13-3 have better solubility in propylene glycol methyl ether acetate solvent than the widely used 2,3,4,4'-tetrahydroxybenzophenone-2,1,5-diazonaphthoquinone sulfonate S19, which is more conducive to the preparation of photoresists.

[0110] Application Example 1

[0111] The diazonaphthoquinone sulfonates P5-1, P10-1, P15-1, P4-2, P2-2, P3-2, P7-3, P11-3, P13-3 provided in Examples 1-9 above, and commercially available S19 were used as photosensitizers and mixed with resin, surfactant, adhesion promoter, and solvent to form a photoresist solution. Based on 100 parts by weight of the photoresist solution, the solvent was 86 parts, the resin was 11 parts, the surfactant was 0.5 parts, the adhesion promoter was 1.0 part, and the photosensitizer was 1.5 parts. The resin was a linear phenolic resin with an average molecular weight of 6000; the solvent was propylene glycol methyl ether acetate; the surfactant was a perfluorinated surfactant; and the adhesion promoter was melamine adhesive.

[0112] The aforementioned photoresist solutions were spin-coated onto silicon wafers. After vacuum drying, they were baked on a hot plate at 110°C for 90 seconds to form a photoresist coating with a thickness of approximately 1.5 μm. The photoresist coating was then exposed using a mercury lamp as the light source, with a total exposure energy of 200–400 mJ / cm². 2 After exposure, the image was developed using a 2.38 wt% tetramethylammonium hydroxide aqueous solution for 20 seconds. After rinsing with water for 30 seconds, it was dried to remove the exposed areas, forming the photoresist pattern. The photoresist pattern was examined using a scanning electron microscope to compare the resolution, with the minimum achievable linewidth as the standard. The resolution test results for different photoresist patterns are shown in Table 2.

[0113] Table 2

[0114] Photoresist composition Minimum resolution (μm) P5-1 Composition 1.5 P10-1 composition 1.7 P15-1 Composition 1.5 P4-2 Composition 2.0 P2-2 composition 3.0 P3-2 Composition 2.5 P7-3 composition 1.6 P11-3 Composition 2.3 P13-3 Composition 2.5 S17 Composition 3.5

[0115] Compared to commercially available photoresist composition S17, the photoresist prepared using diazonaphthoquinone sulfonates P5-1, P10-1, P15-1, P4-2, P2-2, P3-2, P7-3, P11-3, and P13-3 as photosensitizers produces a higher resolution pattern after exposure and development.

Claims

1. A diazonoquinone-type photosensitive compound, characterized in that, The diazonoquinone-type photosensitive compound has the structure shown in Formula I: Formula I Where X represents N, C, Si or benzene ring, R independently represents hydrogen, halogen, C1-C18 branched or straight-chain alkyl, C2-C10 unsaturated hydrocarbon or C3-C12 cycloalkyl, n represents an integer between 0 and 2, m represents an integer between 2 and 4, and D is not entirely H.

2. A diazonoquinone-type photosensitive compound, characterized in that, The structural formula is as follows: D is not entirely H; When the substituent D in the above-mentioned diazonoquinone type photosensitive compound is H or D1, then A in the product name is also 1; when the substituent D is H or D2, A in the product name is 2; when the substituent D is H or D3, A in the product name is 3.

3. The diazonoquinone-type photosensitive compound according to claim 2, characterized in that, The diazonoquinone-type photosensitive compound is selected from at least one of the following structural compounds: D is not entirely H.

4. A method for preparing the diazonoquinone-type photosensitive compound according to claim 1, characterized in that, The preparation method includes: Step A1 involves mixing a polycarbonyl enol compound and diazonoquinone sulfonyl chloride in an organic solvent, and reacting the mixture with an alkaline activator to obtain a diazonoquinone sulfonate product system. The diazonoquinone sulfonyl chloride is selected from at least one of the following structural compounds: The polycarbonyl enol compound has the structure shown in Formula II: Formula II Where X represents N, C, Si or benzene ring, R independently represents hydrogen, halogen, C1-C18 branched or straight-chain alkyl, C2-C10 unsaturated hydrocarbon group, C3-C12 cycloalkyl, n represents an integer between 0 and 2, and m represents an integer between 2 and 4. Step A2: Add hydrochloric acid to the diazonium naphthoquinone sulfonate product system obtained in A1 and filter to remove inorganic salt byproducts. Then add a large amount of water to the organic phase to precipitate the diazonium naphthoquinone sulfonate product. Step A3 involves repeatedly washing and purifying the diazononaphthoquinone sulfonate product with water to obtain a diazononaphthoquinone-type photosensitive compound product.

5. The method for preparing the diazonoquinone-type photosensitive compound according to claim 4, characterized in that, The polycarbonyl enol compound is selected from at least one of the following structural compounds: 。 6. The method for preparing the diazonoquinone-type photosensitive compound according to claim 4, characterized in that, The polycarbonyl enol compound was prepared by the following method: Step A1: Acetyl compounds are synthesized from raw material a through an acylation reaction; Step A2: Synthesis of carboxylic acid compounds via the Willgerodt-Kindler reaction; Step A3: Prepare the Vilsmeier-Haack-Arnold reagent by adding carboxylic acid compounds to the Vilsmeier-Haack-Arnold reagent to synthesize onium salt compounds; Step A4: Hydrolyze the onium salt compound to obtain a polycarbonyl enol compound; Where X represents N, C, Si or benzene ring, R independently represents hydrogen, halogen, C1-C18 branched or straight-chain alkyl, C2-C10 unsaturated hydrocarbon group, C3-C12 cycloalkyl, n represents an integer between 0 and 2, and m represents an integer between 2 and 4.

7. The method for preparing the diazonoquinone-type photosensitive compound according to claim 4, characterized in that, The reaction is carried out under an inert gas protective atmosphere, at a temperature of 20–60°C, and for a time of 0.5–6 h. The alkaline activator includes triethylamine, tripropylamine, ethylenediamine, pyridine, N,N At least one of the following: dimethylaniline, tetramethylammonium hydroxide, sodium methoxide, sodium ethoxide, lithium diisopropylamino, sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium carbonate, potassium bicarbonate, potassium hydroxide, ammonium hydroxide, and sodium hydride.

8. The method for preparing the diazonoquinone-type photosensitive compound according to claim 7, characterized in that, The reaction is carried out under an inert gas protective atmosphere, at a temperature of 25–40°C, and for a time of 1–3 hours. The alkaline activator is at least one of triethylamine, pyridine, and sodium bicarbonate.

9. The method for preparing the diazonoquinone-type photosensitive compound according to claim 4, characterized in that, The diazononaphthoquinone sulfonate product also includes a post-processing procedure, which involves adding the obtained diazononaphthoquinone sulfonate product system to a hydrochloric acid solution for filtration, adding a large amount of water to the filtered organic phase to precipitate the diazononaphthoquinone sulfonate product, and then washing and purifying it with water to obtain a diazononaphthoquinone-type photosensitive compound product.

10. The application of the diazonaphthoquinone sulfonate as described in any one of claims 1-3 in photoresist formulation, characterized in that, The photoresist composition comprises a resin and a photosensitizer, wherein the photosensitizer is a diazonoquinone-type photosensitive compound as described in any one of claims 1-3.

11. The application of the diazonaphthoquinone sulfonate according to claim 10 in photoresist formulation, characterized in that, The resin is a phenolic resin; The weight-average molecular weight (Mw) of phenolic resin is 2000–40000.

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