Sulfonium sulfonate photoacid generator and photoresist composition thereof

Abstract

The invention provides a sulfonium sulfonate photoacid generator and a photoresist composition thereof. The photoacid generator provided by the invention has relatively large molecular weight, can reduce diffusion of a conventional photoacid generator in a use process, and is beneficial to improving a process window and edge roughness of photoresist.

Description

Technical Field

[0001] This invention belongs to the field of photolithography materials technology, specifically relating to a sulfonate matte salt photoacid generator and a photoresist composition containing the photoacid generator. Background Technology

[0002] Photoresist, also known as photoresist, is a crucial core material in the photolithography process. It refers to an etch-resistant material whose solubility changes upon exposure to electromagnetic waves such as ultraviolet light, X-rays, or electron beams. It plays a role in transferring patterns and is widely used in the processing of fine patterns in displays, integrated circuits, microelectromechanical systems (MEMS), and optoelectronic devices. In recent years, the rapid development of large-scale integrated circuits and the display industry has placed higher demands on photolithography processes, requiring the acquisition of more refined and higher-resolution replicated patterns.

[0003] Since the adoption of deep ultraviolet (DUV) light sources in semiconductor integrated circuit photolithography, chemical amplification (CAR) technology has gradually become the mainstream application in the industry. In CAR photoresist technology, the resin is polyethylene, which is difficult to dissolve due to its chemically protected groups. Therefore, CAR photoresist requires the use of photoacid generators (PAGs) as photoinitiators. When the photoresist is exposed, the PAGs in the exposed areas generate an acid. This acid acts as a catalyst during the post-baking process, removing the protecting groups of the resin and making it easier to dissolve. CAR photoresist has an exposure speed 10 times faster than diazonaphthoquinone (DNQ) photoresist, exhibits excellent optical sensitivity to deep ultraviolet light sources, and also offers advantages such as high contrast and high resolution.

[0004] Chemically amplified photoresists generally consist of four main components: film-forming resin, photoacid generator, additives, and solvents. Their mechanism of action involves the photoacid generator absorbing light to produce acid, which causes a deprotection reaction in the film-forming resin, transforming it from insoluble in the developer to soluble in it. Chemically amplified photoresists include KrF photoresists (poly(p-hydroxystyrene) resin system), ArF photoresists (poly(methacrylate) resin system), and some EUV photoresists. These photoresists use photoacid generators (PAGs) as the photosensitive material.

[0005] Compared to KrF photoresist, ArF photoresist's main resin does not contain benzene rings or phenolic hydroxyl groups. Therefore, electrons cannot transfer from the resin to the photoacid generator, and there is no sensitized acid generation. Furthermore, the intensity of the ArF laser is relatively low, and the binding energy of the acid-sensitive groups commonly used in photoresists is high. Therefore, the acid generation efficiency of the photoacid generator in ArF photoresist is lower than that in KrF. A photoacid generator with higher sensitivity, higher acid generation efficiency, and stronger acidity is required to achieve chemical amplification of the ArF photoresist.

[0006] The acid-generating efficiency, thermal stability, acid-generating intensity, and post-photolysis transparency of photoacid generators have a significant impact on photoresist performance. The diffusion length of the photoacid generator directly determines the photoresist performance and some important parameters, such as exposure energy, energy window, edge roughness, pattern morphology, and mask error enhancement factor. An excellent photoacid generator achieves an optimal balance between solubility, stability, sensitivity, and process window.

[0007] Currently used photoacid-generating agents such as TPS-PFBS generally suffer from problems such as small depth of focus (DOF) or poor edge roughness when used for photolithography with ArF photoresists. Summary of the Invention

[0008] To address the shortcomings of existing photoresist formulations with poor process window and edge roughness, this invention provides a novel photoresist. The photoresist provided by this invention has a larger molecular weight, which reduces the diffusion of conventional photoresists during use, thus improving the process window and edge roughness of the photoresist.

[0009] The technical solution of the present invention is as follows: The compound shown in Formula I below,

[0010] I R1 is selected from chemical bonds or C 1-12 Alkylene; R2 is selected from H, halogen, or C. 1-12 alkyl; m can be 0, 1, 2, 3, 4, or 5; R3 is selected from C 1-4 Alkylene; X is a halogen.

[0011] According to an embodiment of the present invention, R1 is selected from chemical bonds or C 1-6 Alkylene; R2 is selected from fluorine, chlorine or C 1-6 Alkyl group; m is 0, 1, 2, 3 or 4; R3 is selected from C 1-4 Alkylene; X is either fluorine or chlorine.

[0012] According to an embodiment of the invention, R2 replaces C represented by R3. 1-4 On the alkylene group and / or the methylene group adjacent to R3.

[0013] According to an embodiment of the present invention, R1 is selected from chemical bonds or C 1-4 Alkylenes, such as methylene, ethylene, propylene, or butylene.

[0014] According to an embodiment of the present invention, R2 is selected from H, fluorine, chlorine or C. 1-6 Alkyl groups, such as R2, are selected from H, fluorine, chlorine, or C. 1-4 Alkyl groups, such as R2, are selected from H, methyl, ethyl, n-propyl, or n-butyl.

[0015] According to an embodiment of the present invention, m is 0, 1, 2, 3 or 4.

[0016] According to an embodiment of the present invention, X is fluorine or chlorine.

[0017] According to an embodiment of the present invention, the compound represented by Formula I is selected from the following compounds:

[0018] R1 is selected from chemical bonds or C 1-4 Alkylenes, such as methylene, ethylene, propylene, or butylene; R 21 R 22 R 23 R 24 They may be the same or different, and are independently selected from H, fluorine, chlorine, or C. 1-4 Alkyl groups, such as H, F, methyl, ethyl, n-propyl; R2 is selected from H, fluorine, chlorine, or C. 1-4 Alkyl groups, such as H, methyl, ethyl, n-propyl, or n-butyl.

[0019] As an example, the compound shown in Formula I is selected from the following structures:

[0020] B2

[0021] B3

[0022] B4

[0023] B5

[0024] B6

[0025] B7

[0026] B8

[0027] B9

[0028] B10

[0029] B11

[0030] The present invention also provides a method for preparing the compound shown in Formula I above, comprising the following steps:

[0031] Wherein, R1, R2, R3, m and X have the definitions described above; The compound of Formula 1A reacts with the compound of Formula 1B to give the compound shown in Formula I.

[0032] According to an embodiment of the present invention, the molar ratio of compound 1A to compound 1B is 1:(0.5-2).

[0033] According to an embodiment of the present invention, the reaction between compound 1A and compound 1B is carried out in the presence of concentrated sulfuric acid.

[0034] According to an embodiment of the present invention, the molar ratio of compound of formula 1A to concentrated sulfuric acid is 1:(0.5-2).

[0035] According to an embodiment of the present invention, the reaction between compound 1A and compound 1B can be promoted by adding a molecular sieve to absorb water.

[0036] According to an embodiment of the present invention, sodium bicarbonate solution is added during the post-reaction treatment of compound 1A and compound 1B to remove excess sulfuric acid.

[0037] According to an embodiment of the present invention, the reaction of compound 1A with compound 1B requires precipitation with isopropyl ether during post-treatment.

[0038] The present invention also provides the use of the compound shown in Formula I above as a photoacid-generating agent.

[0039] The present invention also provides a photoresist composition comprising: a polymer resin and a photoacid generator; wherein the photoacid generator is a compound as shown in Formula I above.

[0040] According to an embodiment of the present invention, the polymer resin is a polymer resin capable of ArF lithography, such as a polymethacrylate resin system.

[0041] According to an embodiment of the present invention, the polymer resin is selected from the following structures:

[0042] P1

[0043] P2

[0044] P3

[0045] P4

[0046] P5

[0047] P6

[0048] P7

[0049] P8

[0050] P9

[0051] P10 The subscript of each structural unit indicates the molar percentage of that structural unit in the polymer.

[0052] According to an embodiment of the present invention, the photoresist composition further includes a solvent. The solvent is selected from one or more of the following substances: propylene glycol methyl ether, ethyl lactate, butyl acetate, propylene glycol methyl ether acetate (PGMEA), propylene glycol dimethyl ether, ethylene glycol monomethyl ether, cyclohexanone (CHO), methyl n-pentanone, methyl isopentanone, cyclopentanone, ethanol, acetonitrile, isopropanol, acetone, and γ-butyrolactone (GBL).

[0053] According to an embodiment of the present invention, the photoresist composition further includes a photoacid diffusion inhibitor. The photoacid diffusion inhibitor is a photoacid diffusion inhibitor suitable for triphenylsulfonate salt systems, for example, selected from at least one of the following structures: D1

[0054] D2

[0055] D3

[0056] D4

[0057] D5

[0058] D6

[0059] D7

[0060] D8

[0061] According to an embodiment of the present invention, the photoresist composition is a chemically amplified photoresist.

[0062] The present invention also provides a photoresist coating comprising the photoresist composition described above.

[0063] The present invention also provides a method for preparing the photoresist coating, comprising: coating the photoresist composition onto a substrate by means of coating (e.g. spin coating) to form a film, thereby obtaining a chemically amplified photoresist.

[0064] In some embodiments of the present invention, the substrate is a silicon wafer or the like.

[0065] The present invention also provides the application of the photoresist coating as described above in photolithography.

[0066] In some embodiments of the present invention, the photoresist coating is used in modern photolithography technologies such as 193nm photolithography, 248nm photolithography, 254nm photolithography, extreme ultraviolet photolithography, nanoimprint lithography, or electron beam lithography.

[0067] In some embodiments of the present invention, when the photoresist coating is used for 193nm photolithography, the exposure energy is set to 15. 50mj / cm 2 .

[0068] The present invention also provides a patterned thin film, wherein the patterned thin film is formed using the photoresist composition. Specifically, the patterned thin film comprises a film layer formed by coating the above-mentioned photoresist composition, followed by exposure and development.

[0069] Beneficial effects The photoacid generator of this invention overcomes the shortcomings of existing photoacid generators, such as poor photoresist process window and edge roughness. The photoacid generator of this invention has a large molecular weight, which reduces diffusion during use and is beneficial for improving the photoresist process window and edge roughness.

[0070] Compared with existing photoacid generators for ArF lithography, the photoacid generator of the present invention significantly improves the edge roughness and process window of the resulting lithographic pattern.

[0071] Terms and Definitions The term "halogen" refers to fluorine, chlorine, bromine, or iodine.

[0072] Term "C" 1-12 "alkyl" should be understood to refer to a straight-chain or branched saturated monovalent hydrocarbon group having 1 to 12 carbon atoms, preferably "C". 1-6 Alkyl group. "C" 1-6 "Alkyl" refers to straight-chain and branched alkyl groups having 1, 2, 3, 4, 5, or 6 carbon atoms. The "C"... 1-12 Alkyl or C 1-6 "Alkyl" is, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neopentyl, 1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl or 1,2-dimethylbutyl, etc., or their isomers. Detailed Implementation

[0073] The technical solution of the present invention will be further described in detail below with reference to specific embodiments. It should be understood that the following embodiments are merely illustrative and explanatory of the present invention, and should not be construed as limiting the scope of protection of the present invention. All technologies implemented based on the above content of the present invention are covered within the scope of protection intended by the present invention.

[0074] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods.

[0075] Photoacid Synthesis Examples Example 1 of photoacid synthesis (1) Synthesis of sodium 1,1,2-trifluoro-4-hydroxybutyrate

[0076] 12.1 g of 3,4,4-trifluoro-3-buten-1-ol, 30.6 g of sodium bisulfite, and 14.2 g of sodium sulfite were dissolved in 230 g of distilled water, and the solution was then heated to 90 °C to initiate the reaction. After stirring for 18 hours, the reaction mixture was cooled to room temperature. The aqueous layer was washed with 30 g of toluene. The solvent was then distilled off using a rotary evaporator to obtain 19.2 g of sodium 1,1,2-trifluoro-4-hydroxybutyrate.

[0077] 1 The H NMR measurement results are shown below. 1 H NMR (400 MHz, CDCl3) δ (ppm): 1.9-2.4 (m, 2H), 3.5-3.7 (m, 2H), 4.9-5.2 (m, 1H).

[0078] (2) Synthesis of sodium 1,1,2-trifluoro-4-(1-adamantanone carbonyloxy)butane-1-sulfonate

[0079] 1.2 g of 2-adamantanone-5-carboxylic acid and 0.2 g of sodium hydride were added to a glass flask equipped with a thermometer, condenser and dropping funnel. Nitrogen gas was purged and the flask was evacuated. Solvent was added to carry out the reaction. After the oxygen was replaced, 20 g of acetonitrile was added through a syringe and the reaction was carried out for 2 hours to prepare reaction solution A.

[0080] In a glass flask equipped with a thermometer, condenser, and dropping funnel, 2.2 g of sodium 1,1,2-trifluoro-4-hydroxybutyrate obtained in step (1) above, 1 g of N,N-carbonyldiimidazole (CDI), and 19.5 g of acetonitrile were added and reacted for 2 hours to prepare reaction solution B. Reaction solution B was then added to reaction solution A via a syringe and reacted for 15 hours. The mixture was concentrated by rotary evaporation. 49.4 g of tert-butyl methyl ether was added to the residue, and the mixture was stirred. The residue was then filtered and dried.

[0081] 1 The H NMR measurement results are shown below. 1 H NMR (DMSO) δ (ppm): 4.85-5.11 (m, 1H), 4.04-4.32 (m, 2H), 1.65-2.31 (m, 15H).

[0082] (3) Synthesis of triphenylsulfonium salt of 1,1,2-trifluoro-4-(1-adamantanone carbonyloxy)butane-1-sulfonic acid

[0083] Add 3.43 g of sodium 1,1,2-trifluoro-4-(1-adamantanone carbonyloxy)butane-1-sulfonate obtained in step (2) above and 31 g of acetonitrile to a glass flask equipped with a thermometer, and then stir.

[0084] An acetonitrile solution consisting of 2.53 g of triphenylsulfonium chloride and 130 g of acetonitrile was added dropwise to an acetonitrile solution of sodium 1,1,2-trifluoro-4-(1-adamantanone carbonyloxy)butane-1-sulfonate. The mixture was stirred vigorously at room temperature for 15 hours. After the reaction was complete, the reaction solution was filtered. The filtered organic phase was concentrated, and the concentrated product was extracted with 70 g of dichloromethane and 50 g of water and washed with water. The product was washed five times with water, and the organic phase was collected. The organic phase was concentrated and dried.

[0085] 1 The H NMR measurement results are shown below. 1 H NMR (CDCl3) δ (ppm): 7.67-7.83 (m, 15H), 5.04-5.28 (m, 1H), 4.15-4.36 (m, 2H), 1.65-2.42 (m, 15H).

[0086] (4) Synthesis of 1,1,2-trifluoro-4-(((1R,3S,5S,7S)-5'5'6'6'-tetrafluorospiro[adamantane-2,2'-[1,3]dioxane]-5-carbonyl)oxy)butane-1-sulfonic acid triphenylsulfonium (acid-producing agent B2)

[0087] Add 6.92 g of 1,1,2-trifluoro-4-(1-adamantanone carbonyloxy)butane-1-sulfonic acid triphenylsulfonium salt, 2.6 g of 2,2,3,3-tetrafluoro-1,4-butanediol, 60 g of chloroform, 0.97 g of molecular sieve, and 0.5 g of concentrated sulfuric acid obtained in step (3) above to a glass flask equipped with a thermometer, condenser, and dropping funnel, and then stir for 30 minutes. After 30 minutes, heat to room temperature and reflux for 9 hours. After reflux for 9 hours, cool to 23°C. Filter out the molecular sieve. Add 17 g of 10% sodium bicarbonate aqueous solution to the obtained reaction mixture, then stir at 23°C for 30 minutes, allow to stand for separation, and collect the organic phase. Add 36.8 g of water to the collected organic layer, stir at room temperature for 10 minutes, and then remove the aqueous layer. Wash with water 4 times in total. After extraction, concentrate by rotary evaporation. Weigh the rotary evaporated product and add 4 times its weight of dichloromethane. Simultaneously, prepare 5 times the weight of the dichloromethane solution in isopropyl ether. Add the dichloromethane solution dropwise into the isopropyl ether to precipitate the product. Filter the precipitate and dry it to obtain acid-producing agent B2.

[0088] 1 The H NMR measurement results are shown below. 1 H NMR (CDCl3) δ (ppm): 7.70-7.95 (m, 15H), 4.85-5.11 (m, 1H), 3.95-4.29 (m, 6H), 1.51-2.20 (m, 15H).

[0089] Example 2 of photoacid synthesis (1) Synthesis of triphenyl sulfonate salt of 1,1,2-trifluoro-4-((1R,3S,5S,7S)-spiro[adamantane-2,2'-[1,3]dioxolane]-5-carbonyl)oxy)butane-1-sulfonic acid (acid-producing agent B3)

[0090] In a glass flask equipped with a thermometer, condenser, and dropping funnel, add 6.92 g of dried trifluoro-4-(1-adamantanone carbonyloxy)butane-1-sulfonic acid triphenylsulfonium, 3.6 g of ethylene glycol, 60 g of trichloromethane, 0.97 g of molecular sieve, and 0.5 g of concentrated sulfuric acid, and stir for 30 minutes. Heat to room temperature and reflux for 9 hours. Cool to 23°C. Filter out the molecular sieve. Add 17 g of a 10% sodium bicarbonate aqueous solution to the obtained reaction mixture, then stir at 23°C for 30 minutes, allow to stand, and collect the organic phase. Add 36.8 g of water to the collected organic layer, stir at room temperature for 10 minutes, and then remove the aqueous layer. Wash with water four times. After extraction, concentrate by rotary evaporation. Weigh the evaporated product and add 4 times the weight of dichloromethane. Simultaneously prepare 5 times the weight of the dichloromethane solution of isopropyl ether. A dichloromethane solution was added dropwise to isopropyl ether to precipitate the precipitate. The precipitate was then filtered and dried to obtain acid-producing agent B3.

[0091] 1 The H NMR measurement results are shown below. 1 H NMR (CDCl3) δ (ppm): 7.65-7.83 (m, 15H), 5.04-5.27 (m, 1H), 4.09-4.35 (m, 2H), 3.88-3.95 (m, 4H), 1.55-2.21 (m, 15H).

[0092] Photoacid Synthesis Example 3 (1) Synthesis of 4-(((1R,3S,5S,7S)-4'-butylspiro[adamantane-2,2'-[1,3]dioxolane]-5-carbonyl)oxy)-1,1,2-trifluorobutane-1-sulfonic acid triphenylsulfonate (acid-producing agent B4)

[0093] In a glass flask equipped with a thermometer, condenser, and dropping funnel, add 6.92 g of dried trifluoro-4-(1-adamantanone carbonyloxy)butane-1-sulfonic acid triphenylsulfonium, 7.6 g of 1,2-hexanediol, 60 g of chloroform, 0.97 g of molecular sieve, and 0.5 g of concentrated sulfuric acid. Stir for 30 minutes, heat to room temperature, reflux for 9 hours, and cool to 23°C. Filter out the molecular sieve. Add 17 g of a 10% sodium bicarbonate aqueous solution to the obtained reaction mixture, stir at 23°C for 30 minutes, allow to stand, and collect the organic phase. Add 36.8 g of water to the collected organic layer, stir at room temperature for 10 minutes, and then remove the aqueous layer. Wash with water four times. After extraction, concentrate by rotary evaporation. Weigh the evaporated product and add 4 times the weight of dichloromethane. Simultaneously prepare 5 times the weight of the dichloromethane solution of isopropyl ether. A dichloromethane solution was added dropwise to isopropyl ether to precipitate the precipitate. The precipitate was then filtered and dried to obtain acid-producing agent B4.

[0094] 1 The H NMR measurement results are shown below. 1 H NMR (CDCl3) δ (ppm): 7.62-7.85 (m, 15H), 5.02-5.30 (m, 1H), 4.11-4.36 (m, 2H), 3.96-4.11 (m, 2H), 3.43-3.56 (m, 1H), 0.79-2.67 (m, 24H).

[0095] Photoresist Formulation Examples Polymer resin P1 Preparation steps of polymer resin P1: In a nitrogen-protected four-necked flask equipped with a stirrer and condenser, 160g of butanone was added beforehand, and the mixture was heated to reflux. 2-Isopropyl-2-methacryloyloxyadamantane (269.8g), 1-ethylcyclopentyl methacrylate (80.3g), initiator AIBN (9.436g), nDT (12g), and a solvent mixture were slowly added over a period of 4 hours. After the addition was complete, stirring was continued for 3 hours. The reaction system was cooled to room temperature after polymerization was complete. The system was added to n-heptane (1500g), and the white solid powder was collected and dried in a vacuum oven at 45°C for 24 hours to obtain copolymer P1 (236.9g, weight-average molecular weight 8310, molecular weight distribution coefficient 1.86).

[0096] The photoacid-producing agents used in Examples 1-3 and Comparative Examples 1-2 are selected from the following structures: B1-1 B1-2

[0097] B2 B3

[0098] B4

[0099] The photoacid diffusion inhibitors used in Examples 1-3 and Comparative Examples 1-2 are selected from the following structures:

[0100] D1 Photoresist formulation Table 1. Photoresist composition (mass ratio)

[0101] Comparative Example 1 A chemically amplified photoresist, comprising the following components in parts by weight: 100 parts of polymer resin P1 Photoacid-producing agent B1-1, 12.8 parts Photoacid diffusion inhibitor D1 7.51 parts 1815 parts of propylene glycol methyl ether acetate 698 parts of cyclohexanone 139 parts of γ-butyrolactone The preparation method of the above-mentioned chemically amplified photoresist is as follows: Add each component according to the formula and stir until completely dissolved. Use the prepared chemically amplified photoresist as follows: The aforementioned chemically amplified photoresist was spin-coated onto a 4-inch silicon wafer at a spin speed of 1800 rpm, resulting in a coating thickness of 800 Å. It was then pre-baked at 90°C for 60 seconds and exposed in an ArF exposure machine at an exposure energy of 28 mJ / cm². 2 After exposure, the wafer is baked at 90°C for 60 seconds. After the wafer cools to room temperature, it is developed with 2.38% TMAH developer for 30 seconds. Finally, it is rinsed with deionized water for 30 seconds to form the required photolithography pattern. The specific photolithography performance data are shown in Table 2.

[0102] Comparative Example 2 Compared with Comparative Example 1, the difference is that the photo-induced acid-producing agent B1-1 is replaced with B1-2, the amount of which is the same, and the preparation and usage methods are the same as those of Comparative Example 1. Specific data are shown in Table 1.

[0103] Application Example 1 Compared with Comparative Example 1, the difference is that the photo-induced acid-producing agent B1-1 is replaced with B2, the amount of material is the same, and the preparation method and usage method are the same as those of Comparative Example 1. Specific data are shown in Table 1.

[0104] Application Example 2 Compared with Comparative Example 1, the difference is that the photo-induced acid-producing agent B1-1 is replaced with B3, the amount of material is the same, and the preparation method and usage method are the same as those of Comparative Example 1. Specific data are shown in Table 1.

[0105] Application Example 3 Compared with Comparative Example 1, the difference is that the photo-induced acid-producing agent B1-1 is replaced with B4, the amount of material is the same, and the preparation method and usage method are the same as those of Comparative Example 1. Specific data are shown in Table 1.

[0106] The detailed test performance results of Comparative Examples 1-2 and Application Examples 1-3 are shown in Table 2.

[0107] Table 2

[0108] As can be seen from the above photolithography data, compared with Comparative Example 1 and Comparative Example 2, when the photoresist composition using the photoacid-generating agent prepared in this invention is used for ArF photolithography, the DOF of the photolithographic pattern is significantly improved, the edge roughness is significantly reduced, and the photolithography effect is significantly better.

[0109] The exemplary embodiments of the present invention have been described above. However, the scope of protection of the present invention is not limited to the above embodiments. Any modifications, equivalent substitutions, improvements, etc., made by those skilled in the art within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. The compound represented by Formula I, I in, R1 is selected from chemical bonds or C. 1-12 Alkylene; R2 is selected from H, halogen, or C. 1-12 alkyl; m can be 0, 1, 2, 3, 4, or 5; R3 is selected from C 1-4 Alkylene; X is a halogen.

2. The compound according to claim 1, wherein, R1 is selected from chemical bonds or C. 1-6 Alkylene; R2 is selected from fluorine, chlorine or C 1-6 Alkyl group; m is 0, 1, 2, 3 or 4; R3 is selected from C 1-4 Alkylene; X is either fluorine or chlorine.

3. The compound according to claim 1 or 2, wherein, R1 is selected from chemical bonds or C. 1-4 Alkylenes, such as methylene, ethylene, propylene, or butylene; Preferably, R2 is selected from H, fluorine, chlorine or C. 1-6 Alkyl groups, such as R2, are selected from H, fluorine, chlorine, or C. 1-4 Alkyl groups, such as R2, are selected from H, methyl, ethyl, n-propyl, or n-butyl; Preferably, m is 0, 1, 2, 3 or 4; Preferably, X is fluorine or chlorine.

4. The compound according to any one of claims 1-3, wherein, The compound represented by Formula I is selected from the compounds shown below: R1 is selected from chemical bonds or C 1-4 Alkylenes, such as methylene, ethylene, propylene, or butylene; R 21 R 22 R 23 R 24 They may be the same or different, and are independently selected from H, fluorine, chlorine, or C. 1-4 Alkyl groups, such as H, F, methyl, ethyl, n-propyl; R1 is selected from chemical bonds or C 1-4 Alkylene; R 21 R 22 R 23 R 24 Same or different, selected from H, fluorine, chlorine or C 1-4 Alkyl group; R2 is selected from H, fluorine, chlorine or C. 1-4 alkyl.

5. The compound according to any one of claims 1-4, wherein, The compound represented by Formula I is selected from the structures shown below: B2 B3 B4 B5 B6 B7 B8 B9 B10 B11。 6. A method for preparing the compound according to any one of claims 1-5, wherein, Includes the following steps: Wherein, R1, R2, R3, m and X have the definitions described in any one of claims 1-5; The compound of Formula 1A reacts with the compound of Formula 1B to give the compound shown in Formula I.

7. A photoresist composition, wherein, include: Polymer resin and photoacid-producing agent; wherein the photoacid-producing agent is a compound according to any one of claims 1-5; Preferably, the polymer resin is a polymethacrylate resin system; Preferably, the polymer resin is selected from the structure shown below: P1 P2 P3 P4 P5 P6 P7 P8 P9 P10 The subscript of each structural unit indicates the molar percentage of that structural unit in the polymer; Preferably, the photoresist composition further includes a solvent; The solvent is selected from one or more of the following substances: propylene glycol methyl ether, ethyl lactate, butyl acetate, propylene glycol methyl ether acetate (PGMEA), propylene glycol dimethyl ether, ethylene glycol monomethyl ether, cyclohexanone (CHO), methyl n-pentanone, methyl isopentanone, cyclopentanone, ethanol, acetonitrile, isopropanol, acetone, and γ-butyrolactone (GBL). Preferably, the photoresist composition further includes a photoacid diffusion inhibitor; The photo-acid diffusion inhibitor is a photo-acid diffusion inhibitor suitable for sulfonic acid triphenylsulfonate systems, and is selected from at least one of the following structures: D1 D2 D3 D4 D5 D6 D7 D8； Preferably, the photoresist composition is a chemically amplified photoresist.

8. A photoresist coating comprising the photoresist composition of claim 7.

9. The photoresist coating of claim 8 is used in photolithography, for example in 193nm photolithography, 248nm photolithography, 254nm photolithography, extreme ultraviolet photolithography, nanoimprint lithography or electron beam lithography.

10. A patterned thin film, the patterned thin film being formed using the photoresist composition of claim 7; preferably, the patterned thin film comprises a film layer formed by coating the photoresist composition of claim 7 into a film and then exposing and developing it.

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