A fluorine-containing resin for immersion photoresist and a preparation method and application thereof
By designing and controlling the reaction conditions with fluorinated resin, the problem of poor compatibility of small molecules in photoresist was solved, resulting in better development effect and chip manufacturing quality, and improving the performance of photoresist.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
- Filing Date
- 2023-07-07
- Publication Date
- 2026-06-16
AI Technical Summary
Traditional photoresists used in immersion lithography suffer from poor compatibility with small-molecule fluorine compounds, which affects the lithography effect. This results in the developer not being able to completely wet the photoresist surface, causing shape distortion and impacting chip manufacturing quality and efficiency.
Fluorinated resins are used to form low surface energy films through the reaction of fluorinated monomers with specific structures and alkyl acrylates, thereby improving the developing effect. Furthermore, by controlling the reaction conditions and the addition ratio, the hydrophobicity is enhanced to improve the spreadability of the developer.
It improves the development effect of photoresist, reduces friction, reduces shape distortion, and improves the quality and efficiency of chip manufacturing.
Smart Images
Figure CN116970119B_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of photoresist technology, particularly to the field of IPC C07C233, and more specifically, to a fluorinated resin for immersion photoresist, its preparation method, and its application. Background Technology
[0002] Photoresist is one of the key materials in integrated circuit manufacturing. With the continuous development of manufacturing technology, the technical requirements for photoresist are becoming increasingly stringent. To meet these demanding process conditions, it is necessary to develop higher-performance photoresist products. In traditional photolithography, the resolution is difficult to improve further due to limitations imposed by the principle of optical diffraction. Furthermore, the shrinking of chip size presents greater challenges in feature depth control and pattern resolution. Immersion lithography technology was proposed against this backdrop. It utilizes a high-refractive-index liquid (such as fluorinated silicone oil) to fill the space between the photoresist and the projection lens, forming a liquid immersion layer. This effectively improves the resolution and depth focus control capabilities of the lithography machine during chip manufacturing, thereby enabling the manufacture of smaller, denser microelectronic chips.
[0003] CN112898185B discloses a fluorinated compound for immersion photoresist and a method for preparing the same. The method includes: adding a preliminary compound, 4-dimethylaminopyridine, 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, and chloroform to a reaction vessel, mixing them thoroughly to form a reaction system; adding N,N-dimethylpropanediamine dropwise to the reaction system, reacting to generate a fluorinated compound; wherein the chemical structure of the preliminary compound is n≧1, an integer. This invention also provides an immersion photoresist with added fluorinated compounds. However, this invention adds fluorinated compounds to the photoresist, and the poor compatibility due to the small molecules affects the photolithography effect of the photoresist to some extent. Summary of the Invention
[0004] The first aspect of the present invention provides a fluorinated resin for immersion photoresist, wherein the raw materials for preparing the fluorinated resin include fluorinated monomers, the structure of which is shown in Formula 1, wherein R1, R2, and R3 include one of hydrogen, fluorine, hydroxyl, trifluoromethyl, perfluoroalkane with 1 to 8 carbons, and fluorinated alkane with 1 to 8 carbons; R4 includes perfluoroalkane with 1 to 8 carbons or some fluorinated alkane; and R5 includes one of hydrogen or methyl.
[0005]
[0006] The raw materials for preparing the fluorinated monomer include compounds shown in Formula 2 and Formula 3, wherein R6 includes one of hydroxyl, chlorine, bromine, and fluorine.
[0007] Preferably, R6 comprises chlorine.
[0008]
[0009] The raw materials for preparing the compound shown in Formula 2 include the compound shown in Formula 4.
[0010]
[0011] The compound represented by Formula 4 includes one of S1-S12.
[0012]
[0013] The applicant's research has found that in the structure of the fluorinated monomer, R1, R2, and R3 include one of the following: hydrogen, fluorine, hydroxyl, trifluoromethyl, perfluoroalkane with 1 to 8 carbon atoms, or fluorinated alkane with 1 to 8 carbon atoms; R4 includes perfluoroalkane with 1 to 8 carbon atoms or some fluorinated alkane. This balances the hydrophobicity and reaction rate of the system, improving the development effect. The fluorinated resin forms a low surface energy film in the photoresist, reducing the friction between the film and the wafer surface, thus providing isolation and protection. The fluorinated monomer needs to possess a certain... A certain degree of hydrophobicity is required. Insufficient hydrophobicity leads to distortion during photolithography, while stronger hydrophobicity makes the surface less susceptible to wetting by liquids. During the development process, if the developer cannot completely wet the photoresist surface, it may cause shape distortion, affecting the quality and efficiency of chip manufacturing. Meanwhile, the fluorinated resin in this invention can further improve the development effect. This may be because the multiple functional groups in the fluorinated monomer, through steric hindrance, increase the reaction rate between the ester groups in the fluorinated monomer and the developer.
[0014] A second aspect of the present invention provides a method for preparing a fluorinated resin for immersion photoresist, comprising the following steps:
[0015] Step 1: Solvent 1 is added to the reaction flask, trifluoroiodomethane is introduced, the compound shown in Formula 4 is added, acid-binding agent 1 is added, and the reaction is carried out under oxygen atmosphere and high-pressure mercury lamp irradiation. After post-treatment, the compound shown in Formula 2 is obtained.
[0016] Step 2: Add solvent 2, the compound shown in formula 2, and acid-binding agent 2 to the reaction flask, and add the compound shown in formula 3 dropwise. After the dropwise addition is completed, carry out a temperature-controlled reaction and obtain the compound shown in formula 1 after post-processing.
[0017] Step 3: Add the compound shown in Formula 1, alkyl acrylate, solvent 3, and initiator to the reaction flask. After dissolution, carry out the reaction under a nitrogen atmosphere. After post-treatment, the product is obtained.
[0018] Preferably, the molar ratio of the compound shown in Formula 2 to the compound shown in Formula 3 is 1:(1-1.2).
[0019] The molar ratio of the compound shown in Formula 4 to trifluoroiodomethane is 1:(2-10).
[0020] Preferably, the molar ratio of the compound shown in Formula 4 to trifluoroiodomethane is 1:2.
[0021] The compound shown in Formula 1 and the alkyl acrylate have a weight ratio of 1:(0.2-2).
[0022] Preferably, the weight ratio of the compound represented by Formula 1 to the alkyl acrylate is 1:(0.2-1).
[0023] Preferably, the weight ratio of the compound represented by Formula 1 to the alkyl acrylate is 1:0.5.
[0024] The trifluoroiodomethyl includes one of the following: trifluoroiodomethyl compound, trifluoroiodomethyl solution, and compound that indirectly produces trifluoroiodomethyl.
[0025] Preferably, the trifluoroiodomethane comprises a trifluoroiodomethane compound.
[0026] The solvent 1 includes at least one of N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and dimethyl sulfoxide.
[0027] Preferably, solvent 1 comprises dimethyl sulfoxide.
[0028] The solvent 2 includes at least one of chloroform, dichloromethane, and chloroethane.
[0029] Preferably, the solvent 2 comprises dichloromethane.
[0030] The solvent 3 includes at least one of tetrahydrofuran, 1,4-dioxane, and acetone.
[0031] Preferably, the solvent 3 comprises tetrahydrofuran.
[0032] The initiator includes at least one of organic peroxides and azo initiators.
[0033] Preferably, the initiator comprises azobisisobutyronitrile.
[0034] The alkyl acrylate includes at least one of tert-butyl acrylate, tert-butyl methacrylate, methyl adamantane acrylate, methyl adamantane methacrylate, and butyl lactone methacrylate.
[0035] Preferably, the alkyl acrylate includes methyladamantane methacrylate.
[0036] The acid-binding agent 1 includes at least one of trimethylamine, triethylamine, ethylenediamine, N,N-diisopropylethylamine, tetraethoxy quaternary ammonium salt, and tetramethylethylenediamine.
[0037] Preferably, the acid-binding agent 1 comprises tetramethylethylenediamine.
[0038] The acid-binding agent 2 includes at least one of trimethylamine, triethylamine, ethylenediamine, N,N-diisopropylethylamine, tetraethoxy quaternary ammonium salt, and tetramethylethylenediamine.
[0039] Preferably, the acid-binding agent 2 comprises triethylamine.
[0040] A third aspect of the present invention provides an application of a fluorinated resin for immersion photoresist, which is used in the preparation of immersion photoresist.
[0041] The raw materials for the immersion photoresist include: a base resin, PAG (photoacid), a quencher, a fluorinated resin, and a solvent.
[0042] The PAG is selected from at least one of sulfonium fluoride sulfonate and iodosulfonium fluoride sulfonate.
[0043] Preferably, the PAG is triphenylthionium salt perfluorobutane sulfonate.
[0044] Preferably, the main resin comprises hydroxyadamantane methacrylate, nonanone methacrylate, and isopropyl methacrylate, wherein the weight ratio of hydroxyadamantane methacrylate, nonanone methacrylate, and isopropyl methacrylate is (5-15):(40-60):(30-50).
[0045] More preferably, the weight ratio of hydroxyadamantane methacrylate, nonanone methacrylate, and isopropyl adamantane methacrylate is 10:50:40.
[0046] The solvent is selected from at least one of propylene glycol monoacetate, propylene glycol methyl ether acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ethyl ether, butyl acetate, methyl ethyl ketone, cycloheptanone, cyclohexanone, neopentyl acetate, γ-butyrolactone, and ethyl lactate.
[0047] Preferably, the solvent is selected from propylene glycol methyl ether acetate.
[0048] The weight ratio of the main resin, PAG, and quencher is 100:(10-20):(1-7).
[0049] Preferably, the weight ratio of the main resin, PAG, and quencher is 100:20:7.
[0050] The fluorinated resin is added to the photoresist at a ratio of 0.01-0.05 wt%.
[0051] Preferably, the fluorinated resin is added to the photoresist at a ratio of 0.03-0.05 wt%.
[0052] More preferably, the fluorinated resin is added to the photoresist at a ratio of 0.05 wt%.
[0053] Beneficial effects:
[0054] 1. In the fluorinated monomer structure, R1, R2, and R3 include one of the following: hydrogen, fluorine, hydroxyl, trifluoromethyl, perfluoroalkane with 1 to 8 carbons, or fluorinated alkane with 1 to 8 carbons; R4 includes perfluoroalkane with 1 to 8 carbons or some fluorinated alkane, which can improve the developing effect.
[0055] 2. R5 includes one of hydrogen or methyl, and R6 includes one of hydroxyl, chlorine, bromine, and fluorine, which can further improve the photolithographic morphology, improve flatness and surface smoothness, and reduce roughness.
[0056] 3. The weight ratio of the compound shown in Formula 1 to the alkyl acrylate is 1:(0.2-2), which can make the hydrophobic angle of the photoresist between 85-95°, thus achieving a better development effect.
[0057] 4. The fluorinated resin is added to the photoresist at a ratio of 0.03-0.05 wt%, which can improve the exposure redundancy of photolithography. Attached Figure Description
[0058] Figure 1 This is the reaction formula for step 1 in Example 1.
[0059] Figure 2 This is the reaction formula for step 2 in Example 1.
[0060] Figure 3 This is the reaction formula for step 3 in Example 1.
[0061] Figure 4 This is a photolithographic topography diagram of Example 1.
[0062] Figure 5 This is a photolithographic topography diagram of Example 2.
[0063] Figure 6 This is a photolithographic topography diagram of Example 3.
[0064] Figure 7 This is a photolithography morphology diagram of Example 4.
[0065] Figure 8 This is a photolithographic topography diagram of Example 5.
[0066] Figure 9 This is a photolithographic topography diagram of Example 6.
[0067] Figure 10 This is a photolithography morphology diagram of Example 7.
[0068] Figure 11 This is a photolithographic topography diagram of Example 8.
[0069] Figure 12 This is a photolithographic topography diagram of Example 9. Detailed Implementation
[0070] Example 1
[0071] A fluorinated resin for immersion photoresist, such as Figure 3 As shown in Figure 5.
[0072] A method for preparing a fluorinated resin for immersion photoresist comprises the following steps:
[0073] Step 1, as follows Figure 1 As shown, 500 g of dimethyl sulfoxide was added to the reaction flask, stirring was started, and trifluoroiodomethane gas was introduced. The gas was absorbed to 376 g, and then 208 g of 1,1,1-trifluoro-2-(trifluoromethyl)pent-4-en-2-ol (CAS: 646-97-9, compound 1) was added. Oxygen was introduced, and 450 g of tetramethylethylenediamine was added. The reaction flask was irradiated with a high-pressure mercury lamp for 36 hours. After the reaction was completed, 4000 mL of pure water and 4000 mL of dichloromethane were added. The mixture was washed three times repeatedly to remove solvent, yielding compound 2, 265 g, with a yield of 90%.
[0074] Step 2, as follows Figure 2 As shown, 9.4 g of compound 2 was added to a reaction flask, along with 200 mL of dichloromethane and 11 g of triethylamine. The mixture was cooled to 0°C. 11.5 g of methacrylamide chloride was added dropwise, and the reaction was carried out at 5°C for 30 minutes. The temperature was then slowly and naturally increased to 25°C. 30 g of pure water was added, and the mixture was washed three times repeatedly. After drying and solvent removal, the mixture was distilled to obtain 25 g of compound 3, with a yield of 70%.
[0075] Step 3, as follows Figure 3 As shown, 80g of compound 3, 40g of methyladamantane methacrylate (compound 4), 315g of tetrahydrofuran, and 5g of azobisisobutyronitrile were added to a 1000mL flask and dissolved thoroughly to obtain a mixed liquid. Nitrogen gas was introduced into the reaction solution for deoxygenation for 30min, and then the solution was refluxed at 79℃ in a constant temperature water bath for 14h to obtain a reaction solution. The reaction solution was quenched with cold water and then added dropwise to a methanol solution at a dropping rate of 10d / min. After the addition was completed, the solution was allowed to stand for 1h and then filtered to obtain fluorinated resin 5, with a mass fraction of Mw = 8500 and PDI = 2.1.
[0076] An application of a fluorinated resin for immersion photoresist, used in the preparation of immersion photoresist.
[0077] The raw materials for the immersion photoresist are: main resin, PAG (photoacid), quencher, fluorinated resin, and solvent.
[0078] The weight ratio of the main resin, PAG, and quencher is 100:10:1.
[0079] The fluorinated resin is added to the photoresist at a ratio of 0.01 wt%.
[0080] The solvent is PGMEA (propylene glycol methyl ether acetate), and the solvent is added to the photoresist at a ratio of 97 wt%.
[0081] The PAG is triphenylthionium salt perfluorobutane sulfonate.
[0082] The quencher is triethylamine.
[0083] The main resin is hydroxyadamantane methacrylate, nonanone methacrylate, and isopropyl methacrylate, and the weight ratio of hydroxyadamantane methacrylate, nonanone methacrylate, and isopropyl methacrylate is 10:50:40.
[0084] Preparation of the immersion photoresist: The main resin, PAG (photoacid), quencher, fluorinated resin, and solvent are mixed evenly to obtain the final product.
[0085] Example 2
[0086] The specific implementation method is the same as in Example 1; the difference is that in Example 2, the weight ratio of the main resin, PAG, and quenching agent is 100:15:1.
[0087] Example 3
[0088] The specific implementation method is the same as in Example 1; the difference is that in Example 3, the weight ratio of the main resin, PAG, and quenching agent is 100:20:1.
[0089] Example 4
[0090] The specific implementation method is the same as in Example 1; the difference is that in Example 4, the weight ratio of the main resin, PAG, and quencher is 100:10:5, and the addition ratio of the fluorinated resin in the photoresist is 0.02wt%.
[0091] Example 5
[0092] The specific implementation method is the same as in Example 1; the difference is that in Example 5: the weight ratio of the main resin, PAG, and quencher is 100:15:5, and the addition ratio of the fluorinated resin in the photoresist is 0.02wt%.
[0093] Example 6
[0094] The specific implementation method is the same as in Example 1; the difference is that in Example 6: the weight ratio of the main resin, PAG, and quencher is 100:20:5, and the addition ratio of the fluorinated resin in the photoresist is 0.02wt%.
[0095] Example 7
[0096] The specific implementation method is the same as in Example 1; the difference is that in Example 7: the weight ratio of the main resin, PAG, and quencher is 100:10:7, and the addition ratio of the fluorinated resin in the photoresist is 0.05wt%.
[0097] Example 8
[0098] The specific implementation method is the same as in Example 1; the difference is that in Example 8: the weight ratio of the main resin, PAG, and quencher is 100:15:7, and the addition ratio of the fluorinated resin in the photoresist is 0.05wt%.
[0099] Example 9
[0100] The specific implementation method is the same as in Example 1; the difference is that in Example 9: the weight ratio of the main resin, PAG, and quencher is 100:20:7, and the addition ratio of the fluorinated resin in the photoresist is 0.05wt%.
[0101] Comparative Example 1
[0102] A method for preparing a fluorinated resin for immersion photoresist comprises the following steps: 80g of 2-methylpropionic-2-enoic acid-5,5,5-trifluoro-4-hydroxy-4-(trifluoromethyl)pent-2-yl ester (CAS: 630414-85-6), 40g of methyladamantane methacrylate, 315g of tetrahydrofuran, and 5g of azobisisobutyronitrile are added to a 1000mL flask and dissolved thoroughly to obtain a mixed liquid; nitrogen gas is introduced into the reaction solution for deoxygenation for 30 minutes, and then the solution is refluxed at 79°C for 14 hours in a constant temperature water bath to obtain a reaction solution; the reaction solution is quenched with cold water and then added dropwise to a methanol solution at a dropping rate of 10 drops / min; after the addition is complete, the solution is allowed to stand for 1 hour and then filtered to obtain the fluorinated resin.
[0103] An application of a fluorinated resin for immersion photoresist, used in the preparation of immersion photoresist.
[0104] The raw materials for the immersion photoresist are: main resin, PAG (photoacid), quencher, fluorinated resin, and solvent.
[0105] The weight ratio of the main resin, PAG, and quencher is 100:20:7, and the fluorinated resin is added to the photoresist at a ratio of 0.05 wt%.
[0106] The solvent is PGMEA (propylene glycol methyl ether acetate), and the solvent is added to the photoresist at a ratio of 97 wt%.
[0107] Preparation of the immersion photoresist: The main resin, PAG (photoacid), quencher, fluorinated resin, and solvent are mixed evenly to obtain the final product.
[0108] Comparative Example 2
[0109] A method for preparing a fluorinated resin for immersion photoresist comprises the following steps: 80g of 2-methylprop-2-enoic acid-4,4,4-trifluoro-3-hydroxy-3-(trifluoromethyl)butyl ester (CAS: 914090-18-9), 40g of methyladamantane methacrylate, 315g of tetrahydrofuran, and 5g of azobisisobutyronitrile are added to a 1000mL flask and dissolved thoroughly to obtain a mixed liquid; nitrogen gas is introduced into the reaction solution for deoxygenation for 30 minutes, and then the solution is refluxed at 79°C for 14 hours in a constant temperature water bath to obtain a reaction solution; the reaction solution is quenched with cold water and then added dropwise to a methanol solution at a dropping rate of 10 drops / min; after the addition is complete, the solution is allowed to stand for 1 hour and then filtered to obtain the fluorinated resin.
[0110] An application of a fluorinated resin for immersion photoresist, used in the preparation of immersion photoresist.
[0111] The raw materials for the immersion photoresist are: main resin, PAG (photoacid), quencher, fluorinated resin, and solvent.
[0112] The weight ratio of the main resin, PAG, and quencher is 100:20:7, and the fluorinated resin is added to the photoresist at a ratio of 0.05 wt%.
[0113] The solvent is PGMEA (propylene glycol methyl ether acetate), and the solvent is added to the photoresist at a ratio of 97 wt%.
[0114] Preparation of the immersion photoresist: The main resin, PAG (photoacid), quencher, fluorinated resin, and solvent are mixed evenly to obtain the final product.
[0115] Comparative Example 3
[0116] A method for preparing a fluorinated resin for immersion photoresist comprises the following steps: 80g of 2-methylpropionic acid-1,1,1,3,3,3-hexafluoropropionic-2-yl ester (CAS: 3063-94-3), 40g of methyladamantane methacrylate, 315g of tetrahydrofuran, and 5g of azobisisobutyronitrile are added to a 1000mL flask and dissolved thoroughly to obtain a mixed liquid; nitrogen gas is introduced into the reaction solution for deoxygenation for 30 minutes, and then the solution is refluxed at 79°C for 14 hours in a constant temperature water bath to obtain a reaction solution; the reaction solution is quenched with cold water and then added dropwise to a methanol solution at a dropping rate of 10 drops / min; after the addition is complete, the solution is allowed to stand for 1 hour and then filtered to obtain the fluorinated resin.
[0117] An application of a fluorinated resin for immersion photoresist, used in the preparation of immersion photoresist.
[0118] The raw materials for the immersion photoresist are: main resin, PAG (photoacid), quencher, fluorinated resin, and solvent.
[0119] The weight ratio of the main resin, PAG, and quencher is 100:20:7, and the fluorinated resin is added to the photoresist at a ratio of 0.05 wt%.
[0120] The solvent is PGMEA (propylene glycol methyl ether acetate), and the solvent is added to the photoresist at a ratio of 97 wt%.
[0121] Preparation of the immersion photoresist: The main resin, PAG (photoacid), quencher, fluorinated resin, and solvent are mixed evenly to obtain the final product.
[0122] Performance testing methods
[0123] 1. The photoresists prepared in Examples 1-9 and Comparative Examples 1-3 were subjected to performance tests, and the test data are listed in Table 1.
[0124] Hydrophobic angle test: Deionized water droplets are added to the surface of the photoresist to be tested. The shape and size of the droplets are observed and measured using a microscope (SDC-100). The hydrophobic angle is calculated using the Coriolis equation or Young equation.
[0125] Reaction rate-acid-base titration test:
[0126] - Prepare the fluorinated resin solution to be tested, and the titrant is an aqueous sodium hydroxide solution.
[0127] - Pour a certain amount of fluorinated resin solution into a titration flask, and add an indicator such as phenolphthalein to the solution to observe the endpoint of the titration reaction. At this time, the indicator will show different colors.
[0128] First, add a certain amount of sodium hydroxide solution dropwise, then slowly add more sodium hydroxide solution while continuously stirring the solution until a color change is observed. This point of change is called the titration endpoint, indicating that all the analyte in the solution has been completely consumed by the titrant. Record the time required for the entire process.
[0129] Record the volume of titrant added at the titration endpoint, and calculate the concentration of the analyte in the solution and the titration rate.
[0130] 2. The photoresists prepared in Examples 1-9 were subjected to photolithographic testing: Coating and development were performed using a Lithius I coating and developing machine from Tokyo Electron, with a photoresist coating thickness of 100 nm. The developer was a 2.38% TMAH aqueous solution. The exposure equipment was an ASML 1900Gi immersion lithography machine from the Netherlands. The illumination conditions were: lens numerical aperture 1.35, illumination mode: ring illumination, XY polarization mode, ring illumination inner diameter 0.7, outer diameter 0.9. The pattern size measurement equipment was a Hitachi CG4000 machine, with a voltage of 500 V and a current setting of 6 pA. The test data are listed in Table 2.
[0131] like Figure 4-12 As shown, the lithographic morphologies of Examples 1-9 are shown in sequence.
[0132] Analysis of the photolithography test results shows that Example 9 has good photolithography performance, high exposure redundancy, moderate energy, good morphology, high flatness, high surface smoothness, and low roughness.
[0133] Performance test data
[0134] Table 1
[0135]
[0136]
[0137] Table 2
[0138] Film thickness(nm) <![CDATA[Exposure energy (mj / cm 2 )]]> Graphic size (nm) Exposure redundancy Example 1 100 28 60 15％ Example 2 100 20 60 13％ Example 3 100 13 60 7％ Example 4 100 27 60 13％ Example 5 100 25 60 15％ Example 6 100 20 60 10％ Example 7 100 42 60 18％ Example 8 100 36 60 15％ Example 9 100 32 60 19％ Comparative Example 1 100 19 60 10％ Comparative Example 2 100 29 60 13％ Comparative Example 3 100 26 60 15％
Claims
1. A fluorinated resin for immersion photoresist, characterized in that, The raw materials for preparing the fluorinated resin include fluorinated monomers, the structure of which is shown in Formula 1. Formula 1; The raw materials for preparing the fluorinated monomer include compound of formula 2 and methacryloyl chloride; Formula 2; The method for preparing the fluorinated resin for immersion photoresist includes the following steps: Step 1: Solvent 1 is added to the reaction flask, trifluoroiodomethyl is introduced, 1,1,1-trifluoro-2-(trifluoromethyl)pent-4-en-2-ol is added, acid-binding agent 1 is added, and the reaction is carried out under oxygen atmosphere and high-pressure mercury lamp irradiation. After post-treatment, the compound shown in Formula 2 is obtained. Step 2: Add solvent 2, the compound shown in Formula 2, and acid-binding agent 2 to the reaction flask, and add methacryloyl chloride dropwise. After the addition is complete, carry out a temperature-controlled reaction and obtain the compound shown in Formula 1 after post-treatment. Step 3: Add the compound shown in Formula 1, methyladamantane methacrylate, solvent 3, and initiator to the reaction flask. After dissolution, carry out the reaction under a nitrogen atmosphere. After post-treatment, the product is obtained. The molar ratio of 1,1,1-trifluoro-2-(trifluoromethyl)pent-4-en-2-ol to trifluoroiodomethane is 1:(2-10). The weight ratio of the compound shown in Formula 1 to methyladamantane methacrylate is 1:(0.2-1).
2. An application of a fluorinated resin for immersion photoresist according to claim 1, characterized in that, The fluorinated resin is used in the preparation of immersion photoresist, wherein the addition ratio of the fluorinated resin in the photoresist is 0.01-0.05 wt%.