Resist, preparation method, composition, glue coating layer and pattern forming method

Abstract

The invention relates to the technical field of photoetching, in particular to a resist, a preparation method, a composition, a gluing layer and a pattern forming method, and the resist is simple in molecular structural formula and controllable in molecular weight; the preparation method is simple, the target compound can be synthesized only through two steps, and the production cost is reduced; a glue coating layer prepared from the resist composition has excellent film forming performance, and the film layer is uniform, compact, stable in chemical property and not prone to deformation, so that it can be guaranteed that the glue coating layer has good performance before being used; the glue coating provided by the invention is used for forming a pattern, the edge of a pattern line is clear, and the resolution ratio is relatively high.

Description

Technical Field

[0001] The present invention relates to the field of lithography technology, and in particular to a resist, a preparation method, a composition, a coated glue layer, and a method for forming a pattern. Background Art

[0002] Molecular glass photoresist is an amorphous material composed of monodisperse organic small molecules, which combines the moldability of traditional polymer photoresists and the precise structural characteristics of small molecule materials. This material exhibits excellent performance during the lithography process and is a type of photoresist with a wide range of applications at present.

[0003] However, this type of photoresist still has the following problems: First, the synthesis and processing costs of molecular glass are relatively high. Compared with traditional photoresists, its preparation process is complex and requires precise molecular design and multi-step synthesis. Second, although molecular glass materials have good thermal stability and chemical stability, their long-term stability and reactivity still need to be further optimized under some extreme conditions.

[0004] Therefore, how to provide a photoresist with a simple synthesis process, controllable process, low production cost, and good film-forming property is a technical problem that needs to be solved urgently at present. Summary of the Invention

[0005] The present invention aims to solve at least one of the technical problems existing in the related art. For this reason, the first object of the present invention is to provide a resist; the second object of the present invention is to provide a preparation method of the resist; the third object of the present invention is to provide a composition; the fourth object of the present invention is to provide a coated glue layer; the fifth object of the present invention is to provide a method for forming a pattern.

[0006] In order to achieve the first object, the technical solution adopted by the present invention is as follows: A resist, the structural formula of which is shown as follows: ; Wherein, R is selected from any one of , and ; n is an integer selected from 1 to 5.

[0007] Furthermore, the structural formula is selected from at least one of the following structural formulas: , , , , , , , , .

[0008] To achieve the second objective, the technical solution adopted by the present invention is as follows: A method for preparing a resist, which is used to prepare the resist described in any one of the above, includes the following steps: S100. Add compound L, base I, and a first solvent to compound . After stirring and dissolving, add a catalyst, and react at 80°C to 120°C for 2 to 6 hours to obtain intermediate ; Among them, X is selected from any one of F, Cl, Br, and I; Compound L is selected from any one of , and ; R1 is selected from , and ; S200. Add the intermediate, base II, and a second solvent to the reaction system, stir and dissolve, and react at 50°C to 80°C for 1 to 5 hours under an inert gas atmosphere to obtain resist .

[0009] Furthermore, in step S100: Base I is selected from at least one of sodium carbonate, cesium carbonate, potassium carbonate, potassium phosphate, tetrabutylammonium fluoride, cesium fluoride, and potassium fluoride; The first solvent is selected from at least one of acetone, toluene, dioxane, tetrahydrofuran, and carbon tetrachloride; The catalyst is selected from at least one of bis(triphenylphosphine)palladium, bis(tritert-butylphosphine)palladium, dichloro(bis(triphenylphosphine))palladium, bis(diphenylphosphine)palladium, tris(triphenylphosphine)palladium, difluoro(bis(triphenylphosphine))palladium, and bis(1,3-bis(diphenylphosphino)propane)palladium; In step S200: Base II is selected from at least one of sodium carbonate, cesium carbonate, potassium carbonate, potassium phosphate, tetrabutylammonium fluoride, cesium fluoride, or potassium fluoride; The second solvent is selected from at least one of sodium hydroxide, potassium hydroxide, and imidazole.

[0010] To achieve the third objective, the technical solution adopted by the present invention is as follows: A composition, including the resist described in any one of the above. By mass percentage, the composition includes the following components: Resist 0.1 to 10%, preferably 2 to 10%, but not limited thereto; The photoacid generator is 0.01 - 1%, but not limited thereto; the main function of the photoacid generator in the negative epoxy molecular photoresist is to undergo a decomposition reaction after absorbing light sources such as ultraviolet light (UV), generating strong acids (usually sulfuric acid or phosphoric acid - like). The generation process of this acid can trigger cross - linking reactions of epoxy groups or acid - catalyzed de - protection reactions, thereby changing the chemical properties of the material. When exposed to ultraviolet light, the acid generated by the decomposition of the photoacid generator acts on the epoxy groups in the resist, causing changes in the solubility of these regions and thus forming clear patterns; The acid diffusion controller is 0 - 0.1%, but not limited thereto; the acid diffusion controller prevents the over - diffusion of the generated acid beyond the exposed area by regulating the diffusion rate of the acid in the photoresist, thereby ensuring clear pattern edges and high resolution; The photoinitiator is 0.01 - 1%, but not limited thereto; the photoinitiator itself usually does not directly generate acid, but after absorbing light, it is excited and transfers energy to initiate a series of chemical reactions, such as free - radical generation, cross - linking reactions, etc. The photoinitiator is used in combination with the photoacid generator to initiate the decomposition reaction of the photoacid generator; The balance is the third solvent, and the solvent is used to adjust the viscosity and coating properties of the photoresist; The working principle of the composition provided by the present invention is as follows: the photoacid generator generates acid under ultraviolet light irradiation, and the acid catalyzes the cross - linking of epoxy groups, making the photoresist in the exposed area insoluble in the developer, while the unexposed area remains soluble. The acid diffusion controller regulates the diffusion of the acid to ensure that it only acts in the exposed area, thereby improving the resolution and accuracy of the pattern.

[0011] Furthermore, the photoacid generator is selected from at least one of triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium trifluoromethanesulfonate, phenyliodonium hexafluorophosphate, phenyliodonium hexafluoroantimonate, 4 - phenylsulfonium perfluorobutanesulfonate, tetraphenylborate tetrafluoride, diphenyliodonium hexafluorophosphate, triphenylthiophenium hexafluorophosphate, tetraphenyltetrafluorophosphate, benzothioxanthene, 2 - (2 - hydroxyphenyl) thioxanthene, camphorquinone, and 9,10 - diphenylanthracene; The acid diffusion controller is selected from at least one of n - octylamine, tri - n - octylamine, N - methyldi - n - octylamine, tert - octylamine, triethylamine, and ethylenediamine; The photoinitiator is selected from at least one of benzophenone and its derivatives, benzodiazole derivatives, phenylbenzophenone, acrylate esters, aziridines, diphenylvinyl compounds, and trifluoromethylstyrene; The third solvent is selected from at least one of propylene glycol monomethyl ether acetate, ethyl lactate, ethylene glycol monomethyl ether, and cyclohexanone.

[0012] To achieve the fourth object, the technical solution adopted by the present invention is: A glue coating, including a resist film and a substrate, is formed by spin-coating the composition described in any one of the above on the substrate to form the resist film.

[0013] Furthermore, the thickness of the resist film is uniform.

[0014] Furthermore, the thickness of the resist film is 80 - 200 nm.

[0015] Furthermore, the material of the substrate is selected from any one of silicon, glass, quartz, copper, tantalum, gold, aluminum, polyimide, alumina, and ceramics.

[0016] To achieve the fifth objective, the technical solution adopted by the present invention is: A method for pattern formation, in which the glue coating described in any one of the above is sequentially subjected to pre-baking, exposure, post-baking, and development treatments to obtain a photoresist pattern.

[0017] Furthermore, the method for pattern formation has the following process: Pre-baking: Remove the solvent by heating to help the resist film adhere evenly to the substrate surface, ensure that the glue coating has appropriate hardness and stability, and improve its flatness; preferably, the equipment used for heating is a horizontal heating plate; Exposure: Apply radiation to the surface of the resist film of the glue coating, and irradiate the formed resist film surface through a predetermined pattern mask; among them, various radiation sources can be used for radiation, including low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, and argon lasers, etc. For example, the radiation can be selected from electromagnetic waves or particle beam radiation, but is not limited thereto; the radiation types can cover microwaves, infrared rays, visible light, ultraviolet light (UV), X-rays, γ-rays, electron beams, proton beams, neutron beams, and ion beams, etc. For example, the wavelength of the electromagnetic wave radiation can be selected as 365 nm ultraviolet light, but is not limited thereto; Post-baking: Promote the cross-linking reaction of the epoxy groups in the resist film by heating to form a cross-linked network insoluble in the developer, further remove the solvent, reduce the volatiles emission of the glue coating in the subsequent process, and improve the accuracy and stability of the pattern; preferably, the equipment used for heating is a horizontal heating plate; Development: The developer dissolves the unexposed (uncross-linked) part of the resist film, while the resist film in the exposed area becomes insoluble due to the cross-linking reaction and thus remains to form the required pattern; The developing solution can be selected from alkaline aqueous solutions or organic solvents. The alkaline aqueous solution can be selected from at least one of sodium hydroxide aqueous solution, ammonium hydroxide aqueous solution, potassium hydroxide aqueous solution, sodium tetrafluoride aqueous solution, sodium carbonate solution, hydrogen peroxide aqueous solution, ammonium chloride aqueous solution, and ammonium acetate aqueous solution. The organic solvent can be selected from at least one of xylene, N-methylpyrrolidone, γ-butyrolactone, propylene glycol monomethyl ether acetate, acetone, tetrahydrofuran, methyl isobutyl ketone, dimethyl sulfoxamide, cyclohexanone, and methyl ethyl ketone; Furthermore, an appropriate amount of water-soluble organic solvent or surfactant can be added to the alkaline aqueous solution for use as a developing solution. The water-soluble organic solvent can be methanol or ethanol, but is not limited thereto; The developing method can be selected from immersion developing or spray developing. In immersion developing, the wafer is completely immersed in the developing solution for a certain period of time to ensure uniform development. In spray developing, a spraying device is used to evenly spray the developing solution onto the wafer surface, and the wafer rotates simultaneously to ensure uniform distribution of the developing solution.

[0018] One or more of the above technical solutions in the embodiments of the present invention have at least one of the following technical effects: The resist, preparation method, composition, coated film layer, and pattern formation method provided by the present invention have a simple molecular structural formula and controllable molecular weight for the resist; the preparation method is simple, and the compound can be synthesized only through two steps, reducing the production cost; the coated film layer prepared from the composition with the resist as the resist component has excellent film-forming properties, with a uniform, dense, and chemically stable film layer that is not easily deformed, thus ensuring good performance before use; using the coated film layer provided by the present invention to form a pattern, the pattern line edges are clear and the resolution is high.

[0019] The additional aspects and advantages of the present invention will be partly given in the following description, partly become obvious from the following description, or be understood through the practice of the present invention. Description of the Drawings

[0020] Figure 1 This is a photoresist pattern obtained by spin-coating the composition provided in Example 1 on a silicon wafer according to Example 8 of the present invention.

[0021] Figure 2 This is a photoresist pattern obtained by spin-coating the composition provided in Example 2 on a silicon wafer according to Example 8 of the present invention. Detailed Embodiments

[0022] To make the objectives, technical solutions and advantages of the present invention clearer, the technical solutions in the present invention will be clearly and completely described below in conjunction with specific embodiments. Obviously, the described embodiments are some, but not all, of the embodiments of the present invention. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without making creative efforts fall within the protection scope of the present invention. The following embodiments are used to illustrate the present invention, but cannot be used to limit the scope of the present invention.

[0023] In the following embodiments, the experimental methods used are conventional methods unless otherwise specified, and the materials, reagents, etc. used are carried out according to the technologies or conditions described in the literature in this field or according to the product specifications. Unless otherwise specified, they can all be obtained from commercial channels.

[0024] Example 1 I. Preparation of intermediate.

[0025] Compound 1,3,5-tribromobenzene (0.40 g, 1.29 mmol), 4-hydroxyphenylboronic acid pinacol ester (1.28 g, 5.80 mmol), Cs2CO3 (700 mg, 2.15 mmol), H2O (4 mL), and purified dioxane (20 mL) were added to a 100 mL Schlenk reaction flask, stirred and dissolved. Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium (20 mg, 0.017 mmol) was added. The reaction was refluxed in an oil bath at 100 °C for 4 h. The reaction was monitored by thin layer chromatography until complete. The temperature of the reaction solution was cooled to room temperature, and dichloromethane and saturated sodium chloride aqueous solution were used as extraction agents for extraction three times continuously. The organic phase was collected, dried with anhydrous sodium sulfate to remove water, and the solid and liquid were separated by filtration. Then the organic phase was rotary evaporated to remove the solvent; it was purified by silica gel adsorption column chromatography with petroleum ether as the eluent to obtain the intermediate , and its 1H NMR analysis is as follows: 1 H NMR (500MHz, CDCl3) δ 7.98 (d, J = 26.6 Hz, 6H), 7.53 - 7.36 (m, 6H), 6.90 - 6.74 (m,6H).

[0026] II. Preparation of resist.

[0027] The intermediate (0.71 g, 2 mmol), imidazole (6.8 mg, 0.1 mmol) and epichlorohydrin (2.78 g, 30 mmol) were added to a 100 mL Schlenk reaction flask, stirred and dissolved to obtain a reaction solution. Under a nitrogen atmosphere, the reaction was refluxed in an oil bath at 115 °C for 2 h until the intermediate reaction was complete (monitored by thin layer chromatography). After cooling to room temperature, the excess epichlorohydrin was removed by rotary evaporation to obtain the reaction product. To this reaction product, 4-methyl-2-pentanone (2 ml) and sodium hydroxide solution (1 mol / L, 1 ml) were added, mixed well, heated to 90 °C, stirred and refluxed for 2 h. After cooling to room temperature, the organic layer and the aqueous layer were separated by extraction, and then the organic matter in the aqueous layer was further extracted with 4-methyl-2-pentanone. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, rotary evaporated to obtain the crude product, and the crude product was recrystallized with 4-methyl-2-pentanone to obtain the resist. , and its 1H NMR analysis is as follows: 1 H NMR (500 MHz, CDCl3) δ 7.74 (s, 3H), 7.56 - 7.42 (m, 6H), 6.92 - 6.78 (m, 6H), 4.11 (ddd, J J = 62.0, 11.4, 5.5 Hz, 6H), 3.35 (p, J J = 5.7 Hz, 3H), 3.05 (dd, J J = 7.2, 5.6 Hz, 3H), 2.77 (dd, J J = 7.1, 5.5 Hz, 3H).

[0028] III. Preparation of the composition.

[0029] 4 g of the resist was dissolved in propylene glycol monomethyl ether acetate (95.94 g), then triphenylsulfonium hexafluoroantimonate (0.04 g) as the photoacid generator, ethylenediamine (0.01 g) as the acid diffusion control agent and benzophenone (0.01 g) as the photoinitiator were added, mixed well, and filtered through a 0.2 μM Teflon film to obtain the resist composition.

[0030] Example 2 In this example, compared with Example 1, the difference is that the amount of triphenylsulfonium hexafluoroantimonate added as the photoacid generator during the preparation of the composition is 0.08 g, and the amount of propylene glycol monomethyl ether acetate added is 95.90 g.

[0031] Example 3 I. Preparation of Intermediate

[0032] Compound 3,3',5,5'-tetrabromobenzene (0.61 g, 1.29 mmol), 3,5-dihydroxybenzeneboronic acid pinacol ester (1.82 g, 7.73 mmol), Cs2CO3 (700 mg, 2.15 mmol), H2O (4 mL), and purified dioxane (20 mL) were added to a 100 mL Schlenk reaction flask, stirred and dissolved. Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium (20 mg, 0.017 mmol) was added. The reaction was refluxed in an oil bath at 100 °C for 4 h, and the reaction was monitored by thin-layer chromatography until completion. The temperature of the reaction solution was cooled to room temperature, and dichloromethane and saturated sodium chloride aqueous solution were used as extraction agents for extraction three times in succession. The organic phase was collected, dried over anhydrous sodium sulfate to remove water, and after filtration to separate the solid and liquid, the organic phase was rotary evaporated to remove the solvent. It was purified by silica gel adsorption column chromatography with petroleum ether as the eluent to obtain the intermediate 1,2,4,5-tetrakis(3-hydroxyphenyl)benzene. The 1H NMR analysis of which is as follows: 1 H NMR (500 MHz, CDCl3) δ10.01 (s, 8H), 7.70 (dd, J J = 19.3, 2.1 Hz, 6H), 6.65 (d, J J = 1.8 Hz, 8H), 6.21(t, J J = 1.8 Hz, 4H).

[0033] II. Preparation of Resist

[0034] The intermediate (1.17 g, 2 mmol), imidazole (6.8 mg, 0.1 mmol), and epichlorohydrin (7.40 g, 80 mmol) were added to a 100 mL Schlenk reaction flask, stirred and dissolved. Under a nitrogen atmosphere, the reaction was refluxed in an oil bath at 115 °C for 2 h until the intermediate reacted completely (monitored by thin-layer chromatography until completion). After cooling to room temperature, the excess epichlorohydrin was removed by rotary evaporation to obtain the reaction product. 4-Methyl-2-pentanone (2 ml) and sodium hydroxide solution (1 mol / L, 1 ml) were added to the reaction product, mixed evenly, heated to 90 °C, stirred and refluxed for 2 h. After cooling to room temperature, the organic layer and the aqueous layer were separated by extraction, and the organic matter in the aqueous layer was further extracted with 4-methyl-2-pentanone. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, rotary evaporated to obtain the crude product, and the crude product was recrystallized with 4-methyl-2-pentanone to obtain the resist. , and its 1H NMR analysis is as follows: 1 H NMR (500 MHz, CDCl3) δ 7.46 (s, 6H), 7.06 (d, J J = 2.3 Hz, 8H), 6.42 (t, J J = 2.2 Hz, 4H), 4.13 (ddd, J J = 48.5, 11.4, 5.5 Hz, 16H), 3.35 (p, J J = 5.7 Hz, 8H), 3.05 (dd, J J = 7.2, 5.6 Hz, 8H), 2.82 (dd, J J = 7.3, 5.5 Hz, 8H).

[0035] III. Preparation of the composition.

[0036] Dissolve 5 g of the resist in ethyl lactate (94.50 g), then add triphenylsulfonium hexafluoroantimonate (0.10 g) as the photoacid generator, ethylenediamine (0.02 g) as the acid diffusion control agent, and benzophenone (0.02 g) as the photoinitiator, mix well, and after filtering through a 0.2 μM Teflon membrane, a resist composition is obtained.

[0037] Example 4 I. Preparation of the intermediate.

[0038] Add 1,3,5-tribromobenzene (0.40 g, 1.29 mmol), 3,5-dihydroxybenzeneboronic acid pinacol ester (1.37 g, 5.80 mmol), Cs2CO3 (700 mg, 2.15 mmol), H2O (4 mL), and purified dioxane (20 mL) to a 100 mL Schlenk reaction flask, stir to dissolve, under a nitrogen atmosphere, add tetrakis(triphenylphosphine)palladium (20 mg, 0.017 mmol), heat in an oil bath at 100 °C, reflux for 4 h, and monitor the reaction to completion by thin layer chromatography; Cool the reaction solution to room temperature, extract continuously three times with dichloromethane and saturated sodium chloride aqueous solution as the extractants, collect the organic phase, use anhydrous sodium sulfate as the desiccant to remove water, filter to separate the solid and liquid, and then rotary evaporate the organic phase to remove the solvent; purify by silica gel adsorption column chromatography, using petroleum ether as the eluent, to obtain the intermediate , and its 1H NMR analysis is as follows: 1 H NMR (500 MHz, CDCl3) δ 10.04 (s, 6H), 7.61 (s, 3H), 6.65 (d, J= 1.8 Hz, 6H), 6.21 (t, J = 1.8 Hz, 3H).

[0039] II. Preparation of the resist.

[0040] Add the intermediate (0.80 g, 2 mmol), imidazole (6.8 mg, 0.1 mmol) and epichlorohydrin (5.55 g, 60 mmol) into a 100 mL Schlenk reaction flask, stir to dissolve to obtain a reaction solution. Under a nitrogen atmosphere, heat in an oil bath at 115 °C and reflux for 2 h until the intermediate completely reacts (monitor the complete reaction by thin layer chromatography). Cool to room temperature, remove the excess epichlorohydrin by rotary evaporation to obtain a reactant. Add 4-methyl-2-pentanone (2 ml) and sodium hydroxide solution (1 mol / L, 1 ml) to this reactant, mix evenly, heat to 90 °C, stir and reflux for 2 h. After cooling to room temperature, extract and separate the organic layer and the aqueous layer, and then further extract the organic matter in the aqueous layer with 4-methyl-2-pentanone. Combine the organic layers, dry over anhydrous sodium sulfate, filter, rotary evaporate to obtain a crude product, and recrystallize the crude product with 4-methyl-2-pentanone to obtain the resist , and its 1H NMR analysis is as follows: 1 H NMR (500 MHz, CDCl3) δ 7.56 (s, 3H), 7.01 (d, J = 2.3 Hz, 6H), 6.58 (t, J = 2.2 Hz, 3H), 4.14 (ddd, J =72.6, 11.4, 5.6 Hz, 12H), 3.35 (p, J = 5.7 Hz, 6H), 2.94 (ddd, J = 115.8, 7.2,5.5 Hz, 12H).

[0041] III. Preparation of the composition.

[0042] Dissolve the resist in propylene glycol monomethyl ether acetate (94.95), add triphenylsulfonium hexafluoroantimonate (0.10 g) as the photoacid generator, ethylenediamine (0.02 g) as the acid diffusion control agent and benzophenone (0.02 g) as the photoinitiator, mix evenly, and filter through a 0.2 μM Teflon film to obtain the resist composition.

[0043] Example 5 I. Preparation of the intermediate.

[0044] Compound 3,3',5,5'-tetrabromobiphenyl (0.61 g, 1.29 mmol), 4-hydroxybenzeneboronic acid pinacol ester (1.70 g, 7.73 mmol), Cs2CO3 (700 mg, 2.15 mmol), H2O (4 mL), and purified dioxane (20 mL) were added to a 100 mL Schlenk reaction flask, stirred and dissolved. Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium (20 mg, 0.017 mmol) was added. The reaction was refluxed in an oil bath at 100 °C for 4 h. The reaction was monitored by thin layer chromatography until completion. The reaction solution was cooled to room temperature, and extracted continuously three times with dichloromethane and saturated sodium chloride aqueous solution as the extractants. The organic phase was collected, dried with anhydrous sodium sulfate to remove water, filtered to separate the solid and liquid, and the organic phase was rotary evaporated to remove the solvent; it was purified by silica gel adsorption column chromatography with petroleum ether as the eluent to obtain the intermediate , and its 1H NMR analysis is as follows: 1 H NMR (500 MHz, CDCl3) δ 7.91(s, 4H), 7.80 - 7.66 (m, 6H), 7.52 - 7.39 (m, 8H), 7.02 - 6.75 (m, 8H).

[0045] II. Preparation of the resist.

[0046] The intermediate (1.05 g, 2 mmol), imidazole (6.8 mg, 0.1 mmol), and epichlorohydrin (3.70 g, 40 mmol) were added to a 100 mL Schlenk reaction flask, stirred and dissolved to obtain a reaction solution. Under a nitrogen atmosphere, the reaction was refluxed in an oil bath at 115 °C for 2 h until the intermediate completely reacted (monitored by thin layer chromatography until completion). It was cooled to room temperature, and the excess epichlorohydrin was removed by rotary evaporation to obtain a reaction product. To this reaction product, 4-methyl-2-pentanone (2 ml) and sodium hydroxide solution (1 mol / L, 1 ml) were added, mixed evenly, heated to 90 °C, stirred and refluxed for 2 hours. After cooling to room temperature, the organic layer and the aqueous layer were separated by extraction, and the organic matter in the aqueous layer was further extracted with 4-methyl-2-pentanone. The organic layers were combined, dried with anhydrous sodium sulfate, filtered, rotary evaporated to obtain a crude product, and the crude product was recrystallized with 4-methyl-2-pentanone to obtain the resist , and its 1H NMR analysis is as follows: 11H NMR (500 MHz, CDCl3) δ 7.73 - 7.64 (m, 6H), 7.55 - 7.43 (m, 8H), 6.96 - 6.78 (m, 8H), 4.09 (ddd, J J = 67.1, 11.4, 5.6 Hz, 8H), 3.35 (p, J J = 5.7 Hz, 4H), 3.05 (dd, J J = 7.2, 5.6 Hz, 4H), 2.77 (dd, J J = 7.1, 5.5 Hz, 4H).

[0047] III. Preparation of the composition.

[0048] Dissolve 4 g of the resist in ethyl lactate (95.89 g), add triphenylsulfonium hexafluoroantimonate (0.09 g) as the photoacid generator, ethylenediamine (0.01 g) as the acid diffusion control agent, and benzophenone (0.01 g) as the photoinitiator, mix evenly, and after filtering through a 0.2 μM Teflon film, a resist composition is obtained.

[0049] Example 6 The difference between this example and Example 3 lies in the different content of each component of the resist composition. By mass fraction, the resist, photoacid generator, acid diffusion control agent, and photoinitiator are 4%, 0.08%, 0.01%, and 0.01% respectively, and the rest are solvents.

[0050] Example 7 The difference between this example and Example 4 lies in the different content of each component of the composition. The resist, photoacid generator, acid diffusion control agent, and photoinitiator are 4%, 0.08%, 0.01%, and 0.01% respectively, and the rest are solvents.

[0051] The photosensitivity, line edge roughness, and initial weight loss temperature T loss of the compositions provided in Examples 1 to 7 are shown in Table 1 as follows: Example 8 Prepare a photoresist pattern as follows: Spin-coat the composition on a 1 cm 2On a silicon wafer, a glue coating is formed by pre-baking at 60 °C for 2 min on a horizontal heating plate. Then, a lithography machine is used to irradiate through a mask. Immediately after exposure, post-baking is carried out at 90 °C for 1 min on the horizontal heating plate, followed by immersion development in methyl isobutyl ketone organic solvent for 30 s, and then rinsing with isopropyl alcohol for 10 s to obtain a photoresist pattern; Among them, the composition prepared in Example 1 is spin-coated on the silicon wafer, and the obtained photoresist pattern is as Figure 1 shown; The composition prepared in Example 2 is spin-coated on the silicon wafer, and the obtained photoresist pattern is as Figure 2 shown.

[0052] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and are not intended to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that they can still modify the technical solutions described in the foregoing embodiments, or perform equivalent replacements for some of the technical features; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A resist, characterized in that, Its structural formula is as follows: ； wherein, R is selected from , and any one of; n is an integer selected from 1 to 5.

2. The resist according to claim 1, wherein The structural formula is selected from at least one of the following structural formulas: 、 、 、 、 、 、 、 、 。 3. A method for preparing a resist, characterized in that, For preparing the resist as described in claim 1 or 2, it includes the following steps: S100. Add compound L, base I and the first solvent to the compound , stir to dissolve, then add a catalyst, react at 80 °C to 120 °C for 2 to 6 h to obtain an intermediate ; Wherein, X is selected from any one of F, Cl, Br, and I; Compound L is selected from , and any one of them; R1 is selected from , and ; S200. Add the intermediate, base II, and the second solvent to the reaction system, stir to dissolve, and react at 50 °C to 80 °C for 1 h to 5 h under an inert gas atmosphere to obtain the resist. .

4. The method for preparing a resist according to claim 3, wherein, In step S100: Base I is selected from at least one of sodium carbonate, cesium carbonate, potassium carbonate, potassium phosphate, tetrabutylammonium fluoride, cesium fluoride, and potassium fluoride; The first solvent is selected from at least one of acetone, toluene, dioxane, tetrahydrofuran, and carbon tetrachloride; The catalyst is selected from at least one of bis(triphenylphosphine)palladium, bis(tritert-butylphosphine)palladium, dichloro(bis(triphenylphosphine))palladium, bis(diphenylphosphine)palladium, tris(triphenylphosphine)palladium, bis(triphenylphosphine)palladium difluoride, and bis(1,3-bis(diphenylphosphine)propane)palladium; In step S200: Base II is selected from at least one of sodium carbonate, cesium carbonate, potassium carbonate, potassium phosphate, tetrabutylammonium fluoride, cesium fluoride, or potassium fluoride; The second solvent is selected from at least one of sodium hydroxide, potassium hydroxide, and imidazole.

5. A composition, characterized in that, Including the resist as described in any one of claim 1 or 2, by mass percentage, the composition includes the following components: Resist 0.1 - 10%; Photoacid generator 0.01 - 1%; Acid diffusion control agent 0 - 0.1%; Photoinitiator 0.01 - 1%; The balance is the third solvent.

6. The composition according to claim 5, wherein The photoacid generator is selected from at least one of triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium trifluoromethanesulfonate, phenyliodonium hexafluorophosphate, phenyliodonium hexafluoroantimonate, 4-phenylsulfonium perfluorobutanesulfonate, tetraphenylborate, diphenyliodonium hexafluorophosphate, triphenylthiophenium hexafluorophosphate, tetraphenyltetrafluorophosphate, benzothioxanthene, 2-(2-hydroxyphenyl)thioxanthene, camphorquinone, and 9,10-diphenylanthracene; The acid diffusion control agent is selected from at least one of n-octylamine, tri-n-octylamine, N-methyl di-n-octylamine, tert-octylamine, triethylamine, and ethylenediamine; The photoinitiator is selected from at least one of benzophenone and its derivatives, benzodiazole derivatives, phenylbenzophenone, acrylate esters, aziridines, diphenylvinyl compounds, and trifluoromethylstyrene; The third solvent is selected from at least one of propylene glycol monomethyl ether acetate, ethyl lactate, ethylene glycol monomethyl ether, and cyclohexanone.

7. Glue coating, characterized in that, Including a resist film and a substrate, the composition as described in claim 5 is spin-coated on the substrate to form the resist film.

8. The glue coating according to claim 7, characterized in that The thickness of the resist film is 80 - 200 nm.

9. The glue coating according to claim 7, characterized in that The material of the substrate is selected from any one of silicon, glass, quartz, copper, tantalum, gold, aluminum, polyimide, alumina, and ceramics.

10. A method for pattern formation, characterized in that, The resist coating as described in claim 7 is sequentially subjected to pre-baking, exposure, post-baking, and development treatments to obtain a photoresist pattern.

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