Adamantane carbonate derived photoacid generator and preparation method thereof

Abstract

The invention provides an adamantane carbonate derived photoacid generator and a preparation method thereof.The method comprises the steps that triphosgene serves as a substrate, the triphosgene, adamantane methanol and organic alkali are dissolved in an organic solvent, after substitution reaction is conducted under the temperature control condition, reaction liquid is filtered and subjected to reduced pressure distillation, and a chloroformate adamantane methyl ester intermediate is obtained; the preparation method comprises the following steps: reacting an intermediate with 2-fluoro-2-bromoethanol and organic alkali in dichloromethane at a controlled temperature to obtain 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester oily matter, sulfonating the oily matter to obtain a 1-adamantane methyl carbonate 2-fluoroethyl ester sodium sulfonate carbonate compound, and reacting the compound with 4-[1-(4-methoxybenzoyl)-2, 2, 4-trimethyl-1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3 The preparation method comprises the following steps: carrying out anion exchange reaction on 2, 2-dimethylpropyl]-[1, 4] oxathietidine-4-onium trifluoroacetate in a mixed system of dichloromethane and water, concentrating an organic phase, and finally crystallizing isopropyl ether to obtain a target product.

Description

Technical Field

[0001] This invention relates to the field of organic synthesis technology, and in particular to an adamantane carbonate-derived photoacid-generating agent and its preparation method. Background Technology

[0002] Photoresist, a key material in photolithography, plays a crucial role in the development of the microelectronics and semiconductor industries. Photoacid generators (PAGs) are one of the core components of photoresist. Under light irradiation, they decompose to produce acid, which acts as a catalyst to detach unstable acid groups suspended on the polymer, thereby altering the polymer's polarity. The performance of PAGs significantly impacts the effectiveness of photoresist, including acid generation efficiency, acid generation intensity, thermal stability, and transparency after photolysis.

[0003] However, existing photoacid generators still have some problems. For example, traditional benzene ring-containing PAGs have strong absorption in 193nm photoresist, affecting the exposure of the photoresist substrate. Furthermore, in immersion lithography, the photoacid generators are easily soluble in water-soluble immersion lithography solutions, leading to lens contamination and deformation of the formed resist pattern. To address these issues, researchers have been exploring novel PAG materials and preparation methods to improve photoresist performance.

[0004] Therefore, developing a novel photoacid generator (PAG) that can improve the resolution and performance of photoresists while overcoming the shortcomings of existing technologies has become a key research focus and challenge. Particularly in immersion lithography, designing a PAG that can effectively suppress acid diffusion and improve light transmittance and thermal stability is an urgent problem to be solved. Summary of the Invention

[0005] Technical problem to be solved: The purpose of this invention is to provide a method for preparing an adamantane carbonate-derived photoacid-generating agent.

[0006] Technical solution: A method for preparing an adamantane carbonate-derived photoacid-generating agent, comprising the following steps: ; Step 1: Add triphosgene to toluene and stir to dissolve at low temperature. Then add an organic base and stir until homogeneous. Add adamantane methanol in batches to react and obtain adamantane methyl chloroformate. Step 2: Dissolve adamantane methyl chloroformate and 2-fluoro-2-bromoethanol in organic solvent 1, add triethylamine dropwise, and esterify to obtain 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester; Step 3: Dissolve 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester in organic solvent 2, add sodium dithionite and sodium carbonate, and obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate through a substitution reaction. Step 4: Dissolve sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate in organic solvent 2, add hydrogen peroxide and potassium bicarbonate, and obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate through oxidation reaction. Step 5: Sodium 2-fluoroethyl carbonate 1-adamantane methyl carbonate and 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxathionium-4-onium trifluoroacetate were subjected to ion exchange in dichloromethane and water to obtain 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxathionium:2-fluoro-sulfonic acid-adamantane methanol carbonate.

[0007] Preferably, the organic base in step one includes one or more of pyridine, piperidine, and N,N-diisopropylethylamine.

[0008] Preferably, in step one, the molar ratio of triphosgene, adamantane methanol, organic base and toluene is 1:1.5~2:3~3.5:15, the reaction temperature is 20~25℃, and the reaction time is 16h.

[0009] Preferably, the organic solvent 1 is dichloromethane; and the organic solvent 2 is acetonitrile.

[0010] Preferably, in step two, the molar ratio of adamantane methyl chloroformate, 2-fluoro-2-bromoethanol, triethylamine and organic solvent 1 is 1:0.7~0.9:1.1~1.3:5, the reaction temperature is 20~25℃, and the reaction time is 14h~16h.

[0011] Preferably, in step three, the molar ratio of 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester, sodium dithionite, sodium carbonate and organic solvent 2 is 1:2.0~2.2:3.0~3.2:5, the reaction temperature is 80~85℃, and the reaction time is 14h~16h.

[0012] Preferably, in step four, the molar ratio of sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate, hydrogen peroxide, potassium bicarbonate, and organic solvent 2 is 1:3.0~3.2:2.0~2.2:5, the reaction temperature is 20~25℃, and the reaction time is 14h~16h.

[0013] Preferably, in step five, the molar ratio of sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfonate and 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxothiohexacyclic butyl-4-onium trifluoroacetate is 1:1~1.2. The mass ratio of the mixed solution of dichloromethane and water is 5:1~5; The mass ratio of [1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxothione-4-onium trifluoroacetate to dichloromethane is 1:5~10.

[0014] A photoacid generator derived from adamantane carbonate, wherein the photoacid generator is prepared by the above-described preparation method.

[0015] Beneficial effects: The preparation method of the present invention has the following advantages: In this invention, triphosgene is used as a substrate to prepare an adamantane methyl chloroformate intermediate through a substitution reaction with adamantane methanol and an organic base. This avoids the problem of strong absorption of traditional benzene ring-containing PAG in 193nm photoresist, effectively improves the exposure performance of the photoresist substrate, and enhances the resolution and performance of the photoresist. This invention prepares an oily substance of 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester by reacting 2-fluoro-2-bromoethanol with an organic base, and obtains a sodium sulfonate compound of 1-adamantane methyl carbonate 2-fluoroethyl ester by sulfonation treatment. This significantly improves the solubility and stability of the photoacid generator in water-soluble immersion lithography solution and effectively inhibits acid diffusion. This invention utilizes 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxothionylbutane-4-onium trifluoroacetate for anion exchange reaction to prepare the target product, avoiding the problems of exposure lens contamination and resist pattern deformation caused by the easy dissolution of traditional photoacid generators in immersion lithography, thus improving the lithography effect; This invention improves reaction efficiency and product yield by optimizing reaction conditions and raw material combinations, while reducing production costs, resulting in good economic benefits. The photoacid-generating agent prepared by this invention has excellent thermal stability and can maintain stable performance during the photolithography process, effectively improving the overall performance and service life of the photoresist. Attached Figure Description

[0016] Figure 1 The preparation steps for 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxathionium:2-fluoro-sulfonic acid-adamantane methanol carbonate salt; Figure 2The 1H NMR spectrum of 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxathionium:2-fluoro-sulfonic acid-adamantane methanol carbonate salt; Figure 3 The FNMR spectrum of 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxathionium:2-fluoro-sulfonic acid-adamantane methanol carbonate salt; Figure 4 HPLC chromatogram of 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxathionium:2-fluoro-sulfonic acid-adamantane methanol carbonate salt; Figure 5 These are the photoresist development images of Embodiment 3 and Comparative Examples 1-4 of the present invention. Detailed Implementation

[0017] The present invention will be further described below with reference to embodiments. These embodiments are illustrative of the present invention, but the present invention is not limited to these embodiments: Example 1

[0018] A method for preparing an adamantane carbonate-derived photoacid-generating agent includes the following steps: Step 1. Add 17.85g of triphosgene to 272g of toluene, cool to -10℃, stir under nitrogen atmosphere for 30min, then add 15.25g of pyridine dropwise and stir below 0℃ for 3h, then add 20g of adamantane methanol in batches and stir at 25℃ for 16h to obtain 15g of adamantane methyl chloroformate. Step 2. Dissolve 15g of adamantane methyl chloroformate and 6.75g of 2-fluoro-2-bromoethanol prepared in Step 1 in 75ml of dichloromethane, cool to -10℃, add 8.25g of triethylamine dropwise, stir at 25℃ for 16h to obtain 18g of 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester. Step 3. Dissolve 18g of 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester prepared in Step 2 in 59.4g of acetonitrile, add 13.5g of sodium dithionite and 8.46g of sodium carbonate, and stir at 80℃ for 16h to obtain 23g of sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate. Step 4. Dissolve 23g of sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate prepared in Step 3 in 45g of acetonitrile, add 13.5g of hydrogen peroxide and 1.4g of potassium bicarbonate, stir at 25℃ for 16h to obtain 20g of sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate. Step 5. 20g of sodium 2-fluoroethyl carbonate 1-adamantane methyl carbonate prepared in Step 4 was subjected to ion exchange with 19.5g of 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxetane-4-onium trifluoroacetate in 100g of dichloromethane and 100g of water. The mixture was stirred at 25°C for 16h to finally obtain 15g of 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxetane:2-fluoro-sulfonic acid-adamantane methanol carbonate. Example 2

[0019] A method for preparing an adamantane carbonate-derived photoacid-generating agent includes the following steps: Step 1. Add 178.5g of triphosgene to 2720g of toluene, cool to -10℃, stir under nitrogen atmosphere for 30min, then add 152.5g of pyridine dropwise and stir below 0℃ for 3h, then add 200g of adamantane methanol in batches and stir at 25℃ for 16h to obtain 150g of adamantane methyl chloroformate. Step 2. Dissolve 150g of adamantane methyl chloroformate and 67.5g of 2-fluoro-2-bromoethanol prepared in Step 1 in 750ml of dichloromethane, cool to -10℃, add 82.5g of triethylamine dropwise, stir at 25℃ for 16h to obtain 180g of 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester; Step 3. Dissolve 180g of 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester prepared in Step 2 in 594g of acetonitrile, add 13.5g of sodium dithionite and 84.6g of sodium carbonate, and stir at 80℃ for 16h to obtain 230g of sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate. Step 4. Dissolve 230g of sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate prepared in Step 3 in 450g of acetonitrile, add 135g of hydrogen peroxide and 14g of potassium bicarbonate, stir at 25℃ for 16h to obtain 200g of sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate. Step 5. 200g of sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfonate prepared in Step 4 was subjected to ion exchange with 195g of 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxetane-4-onium trifluoroacetate in 1000g of dichloromethane and 1000g of water. The mixture was stirred at 25°C for 16h to finally obtain 150g of 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxetane:2-fluoro-sulfonic acid-adamantane methanol carbonate. Example 3

[0020] A method for preparing an adamantane carbonate-derived photoacid-generating agent includes the following steps: Step 1. Add 1785g of triphosgene to 27200g of toluene, cool to -10℃, stir under nitrogen atmosphere for 30min, then add 1525g of pyridine dropwise and stir below 0℃ for 3h, then add 2000g of adamantane methanol in batches and stir at 25℃ for 16h to obtain 1500g of adamantane methyl chloroformate. Step 2. Dissolve 1500g of adamantane methyl chloroformate and 675g of 2-fluoro-2-bromoethanol prepared in Step 1 in 7500ml of dichloromethane, cool to -10℃, add 825g of triethylamine dropwise, stir at 25℃ for 16h to obtain 1800g of 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester; Step 3. Dissolve 1800g of 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester prepared in Step 2 in 5940g of acetonitrile, add 135g of sodium dithionite and 846g of sodium carbonate, and stir at 80℃ for 16h to obtain 2300g of sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate. Step 4. Dissolve 2300g of sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate prepared in Step 3 in 4500g of acetonitrile, add 1350g of hydrogen peroxide and 140g of potassium bicarbonate, stir at 25℃ for 16h to obtain 2000g of sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate. Step 5. 2000g of sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfonate prepared in Step 4 was subjected to ion exchange with 1950g of 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxathionium:2-fluoro-sulfonic acid-adamantane methanol carbonate salt in 10000g of dichloromethane and 10000g of water. The mixture was stirred at 25℃ for 16h to finally obtain 1500g of 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxathionium:2-fluoro-sulfonic acid-adamantane methanol carbonate salt. Table 1 compares the amount of feed in Examples 1, 2, and 3.

[0021] As can be seen from Table 1, the yield of this process is stable and can be used as a route for scale-up production.

[0022] Comparative Example 1 Step 1. Add triphosgene to toluene, cool to -10℃, stir under nitrogen atmosphere for 30 min, then add piperidine dropwise and stir below 0℃ for 3 h, then add adamantane methanol in batches and stir at 25℃ for 16 h to obtain adamantane methyl chloroformate. Step 2. Dissolve the adamantane methyl chloroformate and 2-fluoro-2-bromoethanol prepared in Step 1 in dichloromethane, cool to -10℃, add triethylamine dropwise, and stir at 25℃ for 16 h to obtain 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester. Step 3. Dissolve the 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester prepared in Step 2 in acetonitrile, add sodium dithionite and sodium carbonate, and stir at 80°C for 16 hours to obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate. Step 4. Dissolve the sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate prepared in Step 3 in acetonitrile, add hydrogen peroxide and potassium bicarbonate, stir at 25°C for 16 h to obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate. Step 5. The sodium 2-fluoroethyl carbonate 1-adamantane methyl carbonate prepared in Step 4 is subjected to ion exchange with 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxetane-4-onium trifluoroacetate in dichloromethane and water, and stirred at 25°C for 16 h to finally obtain 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxetane:2-fluoro-sulfonic acid-adamantane methanol carbonate salt; Comparative Example 2 A method for preparing an adamantane carbonate-derived photoacid-generating agent includes the following steps: Step 1. Add triphosgene to toluene, cool to -10℃, stir under nitrogen atmosphere for 30 min, then add N,N-diisopropylethylamine dropwise and stir below 0℃ for 3 h, then add adamantane methanol in batches and stir at 25℃ for 16 h to obtain adamantane methyl chloroformate. Step 2. Dissolve the adamantane methyl chloroformate and 2-fluoro-2-bromoethanol prepared in Step 1 in dichloromethane, cool to -10℃, add triethylamine dropwise, and stir at 25℃ for 16 h to obtain 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester. Step 3. Dissolve the 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester prepared in Step 2 in acetonitrile, add sodium dithionite and sodium carbonate, and stir at 80°C for 16 hours to obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate. Step 4. Dissolve the sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate prepared in Step 3 in acetonitrile, add hydrogen peroxide and potassium bicarbonate, stir at 25°C for 16 h to obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate. Step 5. The sodium 2-fluoroethyl carbonate 1-adamantane methyl carbonate prepared in Step 4 is subjected to ion exchange with 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxetane-4-onium trifluoroacetate in dichloromethane and water, and stirred at 25°C for 16 h to finally obtain 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxetane:2-fluoro-sulfonic acid-adamantane methanol carbonate salt; Table 2 compares the raw materials used in Example 1, Comparative Example 1, and Comparative Example 2.

[0023] As can be seen from Table 2, we selected three organic bases for comparison: pyridine, piperidine, and N,N-diisopropylethylamine. Pyridine had the highest yield. Comparative Example 3 A method for preparing an adamantane carbonate-derived photoacid-generating agent includes the following steps: Step 1. Add triphosgene to toluene, cool to -10℃, stir under nitrogen atmosphere for 30 min, then add pyridine dropwise and stir below 0℃ for 3 h, then add adamantane methanol in batches and stir at 0℃ for 16 h to obtain adamantane methyl chloroformate. Step 2. Dissolve the adamantane methyl chloroformate and 2-fluoro-2-bromoethanol prepared in Step 1 in dichloromethane, cool to -10℃, add triethylamine dropwise, and stir at 25℃ for 16 h to obtain 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester. Step 3. Dissolve the 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester prepared in Step 2 in acetonitrile, add sodium dithionite and sodium carbonate, and stir at 80°C for 16 hours to obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate. Step 4. Dissolve the sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate prepared in Step 3 in acetonitrile, add hydrogen peroxide and potassium bicarbonate, stir at 25°C for 16 h to obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate. Step 5. The sodium 2-fluoroethyl carbonate 1-adamantane methyl carbonate prepared in Step 4 is subjected to ion exchange with 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxetane-4-onium trifluoroacetate in dichloromethane and water, and stirred at 25°C for 16 h to finally obtain 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxetane:2-fluoro-sulfonic acid-adamantane methanol carbonate salt; Comparative Example 4 A method for preparing an adamantane carbonate-derived photoacid-generating agent includes the following steps: Step 1. Add triphosgene to toluene, cool to -10℃, stir under nitrogen atmosphere for 30 min, then add pyridine dropwise and stir below 0℃ for 3 h, then add adamantane methanol in batches and stir at 45℃ for 16 h to obtain adamantane methyl chloroformate. Step 2. Dissolve the adamantane methyl chloroformate and 2-fluoro-2-bromoethanol prepared in Step 1 in dichloromethane, cool to -10℃, add triethylamine dropwise, and stir at 25℃ for 16 h to obtain 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester. Step 3. Dissolve the 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester prepared in Step 2 in acetonitrile, add sodium dithionite and sodium carbonate, and stir at 80°C for 16 hours to obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate. Step 4. Dissolve the sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate prepared in Step 3 in acetonitrile, add hydrogen peroxide and potassium bicarbonate, stir at 25°C for 16 h to obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate. Step 5. The sodium 2-fluoroethyl carbonate 1-adamantane methyl carbonate prepared in Step 4 is subjected to ion exchange with 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxetane-4-onium trifluoroacetate in dichloromethane and water, and stirred at 25°C for 16 h to finally obtain 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxetane:2-fluoro-sulfonic acid-adamantane methanol carbonate salt; Table 3 compares the temperatures of Example 1, Comparative Examples 3 and 4.

[0024] As can be seen from Table 3, the yield is highest at a temperature of 25℃.

[0025] Obviously, the above embodiments are merely illustrative examples for clear explanation and are not intended to limit the implementation. Those skilled in the art will recognize that other variations or modifications can be made based on the above description. It is neither necessary nor possible to exhaustively list all possible implementations here. However, obvious variations or modifications derived therefrom are still within the scope of protection of this invention.

Claims

1. A method for preparing an adamantane carbonate-derived photoacid-generating agent, characterized in that, Includes the following steps: ； Step 1: Add triphosgene to toluene and stir to dissolve at low temperature. Then add an organic base and stir until homogeneous. Add adamantane methanol in batches to react and obtain adamantane methyl chloroformate. Step 2: Dissolve adamantane methyl chloroformate and 2-fluoro-2-bromoethanol in organic solvent 1, add triethylamine dropwise, and esterify to obtain 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester; Step 3: Dissolve 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester in organic solvent 2, add sodium dithionite and sodium carbonate, and obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfinate through a substitution reaction. Step 4: Dissolve sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate in organic solvent 2, add hydrogen peroxide and potassium bicarbonate, and obtain sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate through oxidation reaction. Step 5: Sodium 2-fluoroethyl carbonate 1-adamantane methyl carbonate and 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxathionium-4-onium trifluoroacetate were subjected to ion exchange in dichloromethane and water to obtain 4-[1-(4-methoxy-benzoyl)-2,2-dimethyl-propyl]-[1,4]oxathionium:2-fluoro-sulfonic acid-adamantane methanol carbonate.

2. The method for preparing the adamantane carbonate-derived photoacid-generating agent according to claim 1, characterized in that: The organic base in step one includes one or more of pyridine, piperidine, and N,N-diisopropylethylamine.

3. The method for preparing the adamantane carbonate-derived photoacid-generating agent according to claim 1, characterized in that: In step one, the molar ratio of triphosgene, adamantane methanol, organic base and toluene is 1:1.5~2:3~3.5:15, the reaction temperature is 20~25℃, and the reaction time is 16h.

4. The method for preparing the adamantane carbonate-derived photoacid-generating agent according to claim 1, characterized in that: The organic solvent 1 is dichloromethane; the organic solvent 2 is acetonitrile.

5. The method for preparing an adamantane carbonate-derived photoacid-generating agent according to claim 1, characterized in that: In step two, the molar ratio of adamantane methyl chloroformate, 2-fluoro-2-bromoethanol, triethylamine and organic solvent 1 is 1:0.7~0.9:1.1~1.3:5, the reaction temperature is 20~25℃, and the reaction time is 14~16h.

6. The method for preparing the adamantane carbonate-derived photoacid-generating agent according to claim 1, characterized in that: In step three, the molar ratio of 1-adamantane methyl carbonate 2-bromo-2-fluoroethyl ester, sodium dithionite, sodium carbonate and organic solvent 2 is 1:2.0~2.2:3.0~3.2:5, the reaction temperature is 80~85℃, and the reaction time is 14~16h.

7. The method for preparing an adamantane carbonate-derived photoacid-generating agent according to claim 1, characterized in that: In step four, the molar ratio of sodium 1-adamantane methyl carbonate 2-fluoroethyl sulfinate, hydrogen peroxide, potassium bicarbonate, and organic solvent 2 is 1:3.0~3.2:2.0~2.2:5, the reaction temperature is 20~25℃, and the reaction time is 14~16h.

8. The method for preparing an adamantane carbonate-derived photoacid-generating agent according to claim 1, characterized in that: In step five, the molar ratio of sodium 1-adamantane methyl carbonate 2-fluoroethyl ester sulfonate and 4-[1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxothiohexacyclic butyl-4-onium trifluoroacetate is 1:1~1.

2. The mass ratio of the mixed solution of dichloromethane and water is 5:1~5; The mass ratio of [1-(4-methoxybenzoyl)-2,2-dimethylpropyl]-[1,4]oxothione-4-onium trifluoroacetate to dichloromethane is 1:5~10.

9. A photoacid generator derived from adamantane carbonate, said photoacid generator being prepared by the preparation method according to any one of claims 1 to 8.

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