Diazo naphthoquinone type photosensitive compound and application thereof in preparation of photoresist

Abstract

The invention relates to a photosensitive compound suitable for G / I line photoresist. The main structure of the photosensitive compound is composed of a multi-carbonyl enol compound and diazonaphthoquinone sulfonyl. The invention also provides a synthesis method of the photosensitive compound, the diazo naphthoquinone sulfonate type photosensitive compound with excellent performance can be prepared by using the method, and the component proportion of the photosensitive compound can be adjusted at will. The invention also provides an application of the photosensitive compound in photoresist configuration, and the prepared photoresist has good performance.

Description

Technical Field

[0001] The invention relates to the technical field of photosensitizers, and in particular to a photosensitive compound suitable for i-line photoresist, a preparation method and a photoresist composition. Background Art

[0002] Positive photoresist composed of naphthoquinone diazo type photoinitiator and phenolic resin is the most typical type of photoresist used in G / I line lithography process. As early as 1942, Suess reported the Wolff rearrangement reaction mechanism of naphthoquinone diazo (DNQ): the diazo bond of DNQ will decompose and release N2 under light to generate 1-indenyl carboxylic acid. Its excellent photosensitivity to 436 and 365nm wavelength light sources and its unique structural changes make DNQ an ideal raw material for G / I line photoinitiator.

[0003] However, to apply DNQ-type photoinitiators to the field of semiconductor photoresists, they also need to be able to cooperate with polymer resins. DNQ molecules and phenolic hydroxyl groups on phenolic resins form intermolecular hydrogen bonds, and DNQ-type photoinitiators will couple to the molecular chains of phenolic polymers, reducing their solubility in specific solvents. When DNQ is exposed to ultraviolet light, its structure changes, the intermolecular hydrogen bonds are destroyed, and the dissociation of DNQ-type photoinitiators leads to increased solubility of polymer molecules. Therefore, the exposed part of the photoresist can be dissolved and removed, thereby completing the transfer of the photolithographic pattern.

[0004] The photosensitivity of DNQ-type photoinitiators and their dissolution inhibition performance on resins are mainly affected by the type of graft (backbone). The number and relative position of DNQ groups in a unit photoinitiator can be regulated by combining with different grafts. The increase in the unit number of DNQ groups can enhance the photosensitivity contrast of the photoinitiator, and the distance between the groups will also affect its ability to inhibit the dissolution of polymer resins. Therefore, the synthesis and design of an effective graft structure is the key to enhancing the performance of diazonaphthoquinone photoinitiators. Summary of the invention

[0005] In view of the above reasons, the present invention provides a naphthoquinone diazo type photosensitive compound and its preparation method and application in the preparation of G / I photoresist. The naphthoquinone diazo type photosensitive compound can be used to prepare G / I line photoresist, and the prepared photoresist has better performance.

[0006] To achieve the above object, according to the first part of the present invention, a diazonaphthoquinone sulfonate is provided, wherein the diazonaphthoquinone sulfonate has a structure as shown in the following formula I:

[0007]

[0008] Wherein X each independently represents N, C, Si, a benzene ring and an aromatic heterocycle, R each independently represents hydrogen, a halogen, a C1-C18 alkyl branched or straight chain, an aromatic hydrocarbon, a C2-C10 unsaturated hydrocarbon group, or a C3-C12 cycloalkyl group, wherein 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, and multiple substituents on X are evenly and symmetrically distributed.

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

[0010]

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

[0012] Step A1, mixing a polycarbonyl enol compound and diazonaphthoquinone sulfonyl chloride in an organic solvent, and reacting by adding an alkaline activator to obtain the diazonaphthoquinone sulfonate product system;

[0013] Step A2, adding hydrochloric acid to the diazonaphthoquinone sulfonate product system obtained in A1, filtering to remove inorganic salt by-products, and then adding a large amount of water to the organic phase to precipitate the diazonaphthoquinone sulfonate product;

[0014] Step A3, purifying the diazonaphthoquinone sulfonate product to obtain a diazonaphthoquinone photoinitiator product.

[0015] Further, in the step, 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 0.5-6h, preferably 1-3h; preferably, the alkaline catalyst includes at least one of triethylamine, tripropylamine, ethylenediamine, pyridine, N,N-dimethylaniline, tetramethylammonium hydroxide, sodium methoxide, sodium ethoxide, lithium diisopropylamine, 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 inevitable that the diazonaphthoquinone sulfonate product system is subjected to an impurity removal treatment, and the impurity removal treatment is aimed at removing impurities such as unreacted impurities and reaction by-products. The impurity removal treatment includes adding the obtained diazonaphthoquinone sulfonate product system to a hydrochloric acid solution (1.0-5.0wt%), filtering it, removing inorganic salt by-products, and then adding a large amount of water to the organic phase to precipitate the diazonaphthoquinone sulfonate product, filtering it, and drying it to obtain a diazonaphthoquinone type photoinitiator product.

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

[0018]

[0019] Wherein X each independently represents N, C, Si, benzene ring and aromatic heterocycle, R each independently represents hydrogen, halogen, C1-C18 alkyl branched or straight chain, aromatic hydrocarbon, C2-C10 unsaturated hydrocarbon group, C3-C12 cycloalkyl group, 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, synthesizing an acetyl compound by acylation reaction of raw material a;

[0025] Step A2, synthesizing a carboxylic acid compound by Willgerodt-Kindler reaction;

[0026] Step A3, preparing a Vilsmeier-Haack-Arnold reagent, adding a carboxylic acid compound to the Vilsmeier-Haack-Arnold reagent to synthesize an onium salt compound;

[0027] Step A4, hydrolyzing the onium salt compound to obtain a polycarbonyl enol compound;

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

[0029] Furthermore, in step A1, the molar ratio of raw material a and acetyl chloride is 1:3-8, and more preferably 1:4-6; the reaction is carried out under anhydrous conditions and protected by inert gas, the reaction temperature is 25-55°C, preferably 30-45°C, 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] Furthermore, in step A2, the molar ratio of acetyl compound (raw material b): sulfur powder: sodium hydroxide is 1:6-16:6-16, and more preferably 1:6-12:6-12; the reaction temperature is 90-160°C, and more preferably 100-140°C; the reaction time is 24-36h, and 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, and more preferably 1:120-160:30-50; the reaction is carried out under nitrogen protection, the reaction temperature is 90-120 degrees Celsius, and 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: sodium methoxide is 1:10-30, and more preferably 1:20-25; the reaction is carried out under nitrogen protection, the reaction temperature is preferably 35-45°C, and the reaction time is preferably 8-12h.

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

[0034] The photoresist also includes resin, which is phenolic resin, and the weight average molecular weight Mw of the phenolic resin is 2000-40000.

[0035] Furthermore, the mass proportion of the diazonaphthoquinone sulfonate in the photoresist composition is 0.5-5.0%.

[0036] The scheme provided by the present invention is applied, the naphthoquinone sulfonate diazo ester and the preparation method thereof are used, and the naphthoquinone sulfonate diazo ester type photosensitive compound is applied to a photoresist composition, and the obtained photoresist has higher resolution and good performance. DETAILED DESCRIPTION

[0037] The technical solution of the present invention is further explained below in conjunction with 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 protection scope of the present invention shall be subject to the contents recorded in the claims. Any modification or replacement made by a person skilled in the art to the technical solution of the present invention without creative work shall fall within the protection scope of the present invention.

[0038] In a first typical embodiment of the present application, a diazonaphthoquinone sulfonate is provided, wherein the diazonaphthoquinone sulfonate has a structure shown in the following formula I:

[0039]

[0040] Wherein X each independently represents N, C, Si, a benzene ring and an aromatic heterocycle, R each independently represents hydrogen, a halogen, a C1-C18 alkyl branched or straight chain, an aromatic hydrocarbon, a C2-C10 unsaturated hydrocarbon group, or a C3-C12 cycloalkyl group, wherein 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, and multiple substituents on X are evenly and symmetrically distributed.

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

[0042]

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

[0044] Step A1, mixing a polycarbonyl enol compound and diazonaphthoquinone sulfonyl chloride in an organic solvent, and reacting by adding an alkaline activator to obtain the diazonaphthoquinone sulfonate product system;

[0045] Step A2, adding hydrochloric acid to the diazonaphthoquinone sulfonate product system obtained in A1, filtering to remove inorganic salt by-products, and then adding a large amount of water to the organic phase to precipitate the diazonaphthoquinone sulfonate product;

[0046] Step A3, purifying the diazonaphthoquinone sulfonate product to obtain a diazonaphthoquinone photoinitiator product.

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

[0048]

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

[0050]

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

[0052] In order to further improve the yield and preparation efficiency of polycarbonyl enol compounds and save production energy consumption and costs, the following optimizations were made to the various synthesis conditions involved in the synthesis 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 diisopropylamide, 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] In order to further improve the purification efficiency, preferably in the above step A3, the purification includes at least one of dissolution followed by precipitation, washing, recrystallization, and vacuum drying.

[0055] In order to further improve the efficiency of precipitation after dissolution, the preferred good solvent is 1,4-dioxane, the preferred non-good solvent is ultrapure water, and the preferred ratio of 1,4-dioxane to ultrapure water is 20:80.

[0056] In order to further improve the vacuum drying efficiency, the negative pressure value is preferably 10-500 mbar and the temperature is 40-50°C.

[0057] In some embodiments of the present application, diazonaphthoquinone sulfonate is prepared according to the following steps:

[0058] (1) in an inert gas atmosphere, mixing a polycarbonyl enol compound and DNQ in an organic solvent;

[0059] (2) slowly adding an alkaline activator at room temperature, raising the temperature to the reaction temperature, and then allowing the reaction to mature for a period of time;

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

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

[0062] According to the third part of the present invention, there is also provided an application of a diazonaphthoquinone sulfonate as described in claim 1 in a photoresist configuration, wherein the photoresist composition comprises a resin and a photosensitizer, and the photosensitizer is any one of the diazonaphthoquinone sulfonates provided in the first part or a diazonaphthoquinone ester obtained according to any one of the preparation methods provided in the second part.

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

[0064] Furthermore, it is preferred that the resin is a phenolic resin, and the weight average molecular weight Mw of the phenolic resin is 2,000 to 40,000.

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

[0066] The scheme provided by the present invention is applied, the naphthoquinone sulfonate diazo ester and the preparation method thereof are used, and the naphthoquinone sulfonate diazo ester type photosensitive compound is applied to a photoresist composition, and the obtained photoresist has higher resolution and good performance.

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

[0068] Example 1

[0069] This embodiment provides a method for preparing naphthoquinone diazosulfonate P5-1. The preparation reaction formula is shown below. The specific steps include:

[0070]

[0071] Under the protection of an inert gas atmosphere, 15 g of raw material S5 and 9 g of diazonaphthoquinone compound D1 were dissolved in 250 ml of 1,4-dioxane. The reaction temperature was maintained at 30-35°C, and then 10 g of triethylamine was slowly added dropwise within 1 hour. The mixture was allowed to mature for 1 hour, and then 1.0-1.5 wt% dilute hydrochloric acid was slowly added. After filtration, the filtrate was added to 800 ml of ultrapure water. After filtration, the filter cake was filtered and dried to obtain a light yellow solid product P5-1. HPLC measured the effective content of the esterified product to be 99.2%, and the grafting rate was about 89.2%.

[0072] Example 2

[0073] This embodiment provides a method for preparing naphthoquinone diazosulfonate P10-1. The preparation reaction formula is shown below. The specific steps include:

[0074]

[0075] The difference between the preparation method of Example 2 and Example 1 is that the raw material S5 is replaced by 15 g of raw material S10, 16 g of diazonaphthoquinone D1, and other conditions remain unchanged. A light yellow solid product P10-1 is obtained, and the effective content of the esterified product measured by HPLC is 99.4%, and the grafting rate is about 81.7%.

[0076] Example 3

[0077] This embodiment provides a method for preparing naphthoquinone diazosulfonate P15-1. The reaction formula for its preparation is shown below. The specific steps include:

[0078]

[0079] The difference between the preparation method of Example 3 and Example 1 is that the raw material S5 is replaced by 15 g of raw material S15, 11 g of diazonaphthoquinone D1, and other conditions remain unchanged. A light yellow solid product P15-1 is obtained, and the effective content of the esterified product measured by HPLC is 99.2%, and the grafting rate is about 87.4%.

[0080] Example 4

[0081] This embodiment provides a method for preparing naphthoquinone diazosulfonate P4-2. The preparation reaction formula is shown below. The specific steps include:

[0082]

[0083] The difference between the preparation method of Example 4 and Example 1 is that the raw material S5 is replaced by 15 g of raw material S4, the diazonaphthoquinone D1 is replaced by 15 g of diazonaphthoquinone D2, and other conditions remain unchanged. A light yellow solid product P4-2 is obtained, and the effective content of the esterified product measured by HPLC is 98.7%, and the grafting rate is about 83.7%.

[0084] Example 5

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

[0086]

[0087] The difference between the preparation method of Example 5 and Example 1 is that the raw material S5 is replaced by 15 g of raw material S2, 11 g of diazonaphthoquinone D2, and other conditions remain unchanged. A light yellow solid product P2-2 is obtained, and the effective content of the esterified product measured by HPLC is 99.4%, and the grafting rate is about 85.7%.

[0088] Example 6

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

[0090]

[0091] The difference between the preparation method of Application Example 6 and Application Example 1 is that the raw material S5 is replaced by 15 g of raw material S3, 17 g of diazonaphthoquinone D2, and other conditions remain unchanged. A light yellow solid product P3-2 is obtained, and the effective content of the esterified product measured by HPLC is 98.6%, and the grafting rate is 84.9%.

[0092] Example 7

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

[0094]

[0095] The difference between the preparation method of Application Example 7 and Application Example 1 is that the raw material S5 is replaced by 15 g of raw material S7, 8 g of diazonaphthoquinone D3, and other conditions remain unchanged. A light yellow solid product P7-3 is obtained, and the effective content of the esterified product measured by HPLC is 99.1%, and the grafting rate is 87.9%.

[0096] Example 8

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

[0098]

[0099] The difference between the preparation method of Example 4 and Example 1 is that the raw material S5 is replaced by 15 g of raw material S11, 13 g of diazonaphthoquinone D3, and other conditions remain unchanged. A light yellow solid product S11-3 is obtained, and the effective content of the esterified product measured by HPLC is 98.9%, and the grafting rate is 84.5%.

[0100] Example 9

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

[0102]

[0103] The difference between the preparation method of Example 9 and Example 1 is that the raw material S5 is replaced by 15.0 g of the raw material S13, the diazonaphthoquinone compound D1 is replaced by 16 g of D3, and the other conditions remain unchanged. A light yellow solid product S13-3 is obtained, and the effective content of the esterified product measured by HPLC is 99.3%, and the grafting rate is 89.3%.

[0104] Comparative Example 1

[0105] The solubility of compound S19 (2,3,4,4'-tetrahydroxybenzophenone-2,1,5-diazonaphthoquinone sulfonate, a commercial product) and 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 was tested respectively. The results are shown in Table 1 below.

[0106] The solubility test method is as follows: at room temperature of 20±0.5℃, take 5ml of propylene glycol methyl ether acetate as solvent, add the sample to the solvent while stirring until insoluble sample solid appears, continue stirring for 10 minutes until the sample no longer dissolves, then draw about 2ml of the upper clear liquid through a 25μm filter head and drop it into an evaporating dish and weigh it, record the data as m1, then put the evaporating dish in a 40℃ vacuum drying dish to evaporate the solvent, and weigh it again 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] It can be seen from Table 1 that all the novel diazo naphthoquinone sulfonate photosensitive compounds of the present invention have good solubility in propylene glycol methyl ether acetate solvent, just like the 2,3,4,4'-tetrahydroxybenzophenone-2,1,5-diazo naphthoquinone sulfonate S19 widely used on the market. Among them, the novel diazo naphthoquinone 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 2,3,4,4'-tetrahydroxybenzophenone-2,1,5-diazo naphthoquinone sulfonate S19 widely used on the market, which is more conducive to the preparation of photoresist.

[0110] Application Example 1

[0111] The naphthoquinone diazosulfonates P5-1, P10-1, P15-1, P4-2, P2-2, P3-2, P7-3, P11-3, P13-3 and commercially available S19 provided in the above examples 1-9 are respectively used as photosensitizers and mixed with resin, surfactant, adhesion promoter and solvent to form a photoresist solution. Taking the photoresist solution as 100 parts by mass, the solvent is 86 parts, the resin is 11 parts, the surfactant is 0.5 parts, the adhesion promoter is 1.0 parts, and the photosensitizer is 1.5 parts. Among them, the resin is a linear phenolic resin with an average molecular weight of 6000; the solvent is propylene glycol methyl ether acetate; the surfactant is a perfluoro surfactant; and the adhesion promoter is a melamine adhesive.

[0112] The above photoresist solutions were respectively coated on silicon wafers by spin coating, and after vacuum drying, they were baked on a hot plate at 110°C for 90 seconds to form a photoresist coating with a coating thickness of about 1.5 μm. Then, a mercury lamp was used as a light source to expose the photoresist coating with a total exposure energy of 200 to 400 mJ / cm 2 . After exposure, it was developed with a tetramethylammonium hydroxide aqueous solution with a mass concentration of 2.38wt%, and the development time was 20s. After washing with water for 30s, it was dried to remove the exposed part to form a photoresist pattern. The photoresist pattern was inspected using a scanning electron microscope to compare the resolution of the photoresist. The resolution was based on the minimum line width that could be achieved. The resolution test results of 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 with the commercially available photoresist composition S17, the photoresists prepared with diazonaphthoquinone sulfonates P5-1, P10-1, P15-1, P4-2, P2-2, P3-2, P7-3, P11-3, and P13-3 as photosensitizers have higher resolution of the formed graphics after exposure and development.

Claims

1. A naphthoquinone diazine type photosensitive compound, characterized in that: The naphthoquinone diazine type photosensitive compound has a structure shown in the following formula I: Wherein X each independently represents N, C, Si, benzene ring and aromatic heterocycle, R each independently represents hydrogen, halogen, C1-C18 alkyl branched or straight chain, aromatic hydrocarbon, C2-C10 unsaturated hydrocarbon group, C3-C12 cycloalkyl group, wherein 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.

2. The diazonaphthoquinone type photosensitive compound according to claim 1, characterized in that Multiple substituents on X are evenly and symmetrically distributed, and the structural formula includes the following: When the substituent D in the above naphthoquinone diazide photosensitive compound is H or D1, 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 diazonaphthoquinone type photosensitive compound according to claim 2, characterized in that: The naphthoquinone diazide photosensitive compound is selected from at least one of the following structural compounds:

4. A method for preparing the diazonaphthoquinone type photosensitive compound according to any one of claims 1 to 3, characterized in that: The preparation method comprises: Step A1, mixing a polycarbonyl enol compound and diazonaphthoquinone sulfonyl chloride in an organic solvent, and reacting by adding an alkaline activator to obtain the diazonaphthoquinone sulfonate product system; Step A2, adding hydrochloric acid to the diazonaphthoquinone sulfonate product system obtained in A1, filtering to remove inorganic salt by-products, and then adding a large amount of water to the organic phase to precipitate the diazonaphthoquinone sulfonate product; Step A3, washing and purifying the diazonaphthoquinone sulfonate product with water for multiple times to obtain a diazonaphthoquinone type photosensitive compound product.

5. The diazonaphthoquinonesulfonyl chloride according to claim 4 is selected from at least one of the following structural compounds:

6. The method for preparing the diazonaphthoquinone type photosensitive compound according to claim 4, characterized in that: The polycarbonyl enol compound has a structure shown in Formula II: Wherein X each independently represents N, C, Si, benzene ring and aromatic heterocycle, R each independently represents hydrogen, halogen, C1-C18 alkyl branched or straight chain, aromatic hydrocarbon, C2-C10 unsaturated hydrocarbon group, C3-C12 cycloalkyl group, n represents an integer between 0 and 2, and m represents an integer between 2 and 4.

7. The method for preparing the diazonaphthoquinone 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:

8. The method for preparing the diazonaphthoquinone type photosensitive compound according to claim 6, characterized in that: The polycarbonyl enol compound is prepared by the following method: Step A1, synthesizing an acetyl compound by acylation reaction of raw material a; Step A2, synthesizing a carboxylic acid compound by Willgerodt-Kindler reaction; Step A3, preparing a Vilsmeier-Haack-Arnold reagent, adding a carboxylic acid compound to the Vilsmeier-Haack-Arnold reagent to synthesize an onium salt compound; Step A4, hydrolyzing the onium salt compound to obtain a polycarbonyl enol compound; X, R, m, n and the polycarbonyl enol compound have the same meanings as in any one of the above claim 1.

9. The method for preparing a naphthoquinone diazide photosensitive compound according to claim 4, characterized in that: The reaction is carried out under an inert gas protective atmosphere, the reaction temperature is 20 to 60° C., preferably 25 to 40° C., and the reaction time is 0.5 to 6 hours, preferably 1 to 3 hours; The alkaline activator includes at least one of triethylamine, tripropylamine, ethylenediamine, pyridine, N,N-dimethylaniline, tetramethylammonium hydroxide, sodium methoxide, sodium ethoxide, lithium diisopropylamide, 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.

10. The method for preparing the diazonaphthoquinone type photosensitive compound according to claim 4, characterized in that: The diazonaphthoquinone sulfonate product also includes a post-treatment process, in which the obtained diazonaphthoquinone sulfonate product system is added with a hydrochloric acid solution and filtered, and then a large amount of water is added to the organic phase to precipitate the diazonaphthoquinone sulfonate product, which is then washed and purified to obtain a diazonaphthoquinone type photosensitive compound product.

11. A use of the diazonaphthoquinone sulfonate as claimed in claim 1 in photoresist preparation, characterized in that: The photoresist composition comprises a resin and a photosensitizer, wherein the photosensitizer is the diazonaphthoquinone sulfonate according to claim 2; Preferably, the resin is a phenolic resin; More preferably, the weight average molecular weight Mw of the phenolic resin is 2,000 to 40,000.

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