Resist, method of preparation, composition, adhesive layer, and method of pattern formation

Abstract

The present application relates to the field of photoetching technology, and especially relates to a resist, a preparation method, a composition, a glue coating layer and a pattern forming method; the molecular structural formula of the resist is simple, and the molecular weight is controllable; the preparation method is simple, the target compound can be synthesized through only two steps, and the production cost is reduced; the glue coating layer prepared by using the above resist composition has excellent film forming performance, the film layer is uniform and dense, the chemical property is stable, and the glue coating layer is not easy to deform, so that the glue coating layer can guarantee good performance before use; the pattern formed by using the glue coating layer provided by the present application has clear pattern line edges and high resolution.

Description

Technical Field

[0001] This invention relates to the field of photolithography, and more particularly to photoresists, preparation methods, compositions, coating layers, and methods for pattern formation. Background Technology

[0002] Molecular glass photoresist is an amorphous material composed of monodisperse organic small molecules. It combines the molding properties of traditional polymer photoresists with the precise structural characteristics of small molecule materials. This material exhibits excellent performance in the photolithography process and is currently one of the most widely used photoresists.

[0003] However, this type of photoresist still has the following problems: First, the synthesis and processing cost of molecular glass is 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 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 resist with a simple synthesis process, controllable process, low production cost, and good film-forming properties is a technical problem that urgently needs to be solved. Summary of the Invention

[0005] The present invention aims to at least solve one of the technical problems existing in the related art. To this end, the first objective of the present invention is to provide a photoresist; the second objective is to provide a method for preparing the photoresist; the third objective is to provide a composition; the fourth objective is to provide an adhesive coating; and the fifth objective is to provide a method for pattern formation.

[0006] To achieve the first objective, the technical solution adopted by this invention is as follows:

[0007] The corrosion resist has the following structural formula:

[0008] ;

[0009] Where R is selected from , and any one of them;

[0010] n is an integer selected from 1 to 5.

[0011] Furthermore, the structural formula is selected from at least one of the following structural formulas:

[0012] , , , , , , , , .

[0013] To achieve the second objective, the technical solution adopted by this invention is as follows:

[0014] A method for preparing the resist as described in any one of the above-mentioned methods, comprising the following steps:

[0015] S100, To the compound Compound L, base I, and the first solvent are added to the mixture, stirred until dissolved, and then the catalyst is added. The mixture is reacted at 80℃~120℃ for 2~6 hours to obtain the intermediate. ;

[0016] Wherein, X is selected from any one of F, Cl, Br, and I;

[0017] Compound L is selected from , and any one of them;

[0018] R1 is selected from , and ;

[0019] S200. The intermediate, base II, and second solvent are added to the reaction system, stirred to dissolve, and reacted at 50°C–80°C for 1–5 hours under an inert gas atmosphere to obtain the corrosion resist. .

[0020] Furthermore, in step S100:

[0021] Base I is selected from at least one of sodium carbonate, cesium carbonate, potassium carbonate, potassium phosphate, tetrabutylammonium fluoride, cesium fluoride, and potassium fluoride;

[0022] The first solvent is selected from at least one of acetone, toluene, dioxane, tetrahydrofuran, and carbon tetrachloride;

[0023] The catalyst is selected from at least one of bis(triphenylphosphine)palladium, bis(tri-tert-butylphosphine)palladium, bis(triphenylphosphine)chloride, bis(diphenylphosphine)palladium, tri(triphenylphosphine)palladium, bis(triphenylphosphine)difluoride, and bis(1,3-bis(diphenylphosphine)propane)palladium;

[0024] In step S200:

[0025] Base II is selected from at least one of sodium carbonate, cesium carbonate, potassium carbonate, potassium phosphate, tetrabutylammonium fluoride, cesium fluoride, or potassium fluoride;

[0026] The second solvent is selected from at least one of sodium hydroxide, potassium hydroxide, and imidazole.

[0027] To achieve the third objective, the technical solution adopted by this invention is as follows:

[0028] The composition, comprising the resist described in any one of the preceding claims, and by mass percentage, the composition comprises the following components:

[0029] The corrosion resist is 0.1-10%, preferably 2-10%, but not limited thereto;

[0030] The photoacid generator is used at a concentration of 0.01% to 1%, but is not limited to this. Its main function in negative epoxy photoresists is to decompose upon absorbing ultraviolet (UV) light, generating strong acids (usually sulfuric acid or phosphoric acid). This acid formation process can trigger cross-linking reactions of epoxy groups or acid-catalyzed deprotection reactions, thereby altering the chemical properties of the material. When exposed to UV light, the acid produced by the decomposition of the photoacid generator acts on the epoxy groups in the resist, causing changes in the solubility of these areas and ultimately forming a clear pattern.

[0031] The acid diffusion control agent is 0-0.1%, but not limited to this; the acid diffusion control agent prevents the acid from diffusing excessively outside the exposure area by adjusting the diffusion rate of the generated acid in the photoresist, thereby ensuring clear edges and high resolution of the pattern;

[0032] The photoinitiator is used in the range of 0.01% to 1%, but is not limited to this range. The photoinitiator itself usually does not directly generate acid, but is excited by light absorption and transfers energy to initiate a series of chemical reactions, such as free radical generation and cross-linking reactions. The photoinitiator is used in conjunction with the photoacid generator to initiate the decomposition reaction of the photoacid generator.

[0033] The remainder is a third solvent, which is used to adjust the viscosity and coating properties of the photoresist;

[0034] The working principle of the composition provided by the present invention is as follows: under ultraviolet light irradiation, the photoacid generator produces acid, which 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 control agent regulates the diffusion of acid to ensure that it only works in the exposed area, thereby improving the resolution and accuracy of the pattern.

[0035] Furthermore, the photoacid-generating agent is selected from at least one of triphenylsulfonyl hexafluorophosphate, triphenylsulfonyl hexafluoroantimonate, triphenylsulfonyl trifluoromethanesulfonate, phenyliodoene hexafluorophosphate, phenyliodoene hexafluoroantimonate, 4-phenylsulfonyl perfluorobutane sulfonate, tetraphenyltetrafluoroborate, diphenyliodoene hexafluorophosphate, triphenylthiophene sulfonyl hexafluorophosphate, tetraphenyltetrafluorophosphate, benzothiaxanthrone, 2-(2-hydroxyphenyl)thiaxanthrone, camphorquinone, and 9,10-diphenylanthracene;

[0036] The acid diffusion control agent is selected from at least one of n-octylamine, tri-n-octylamine, N-methyldi-n-octylamine, tert-octylamine, triethylamine, and ethylenediamine;

[0037] The photoinitiator is selected from at least one of benzophenone and its derivatives, benzodiazepine derivatives, phenylbenzophenone, acrylates, azacyclic alkenes, diphenylvinyl compounds and trifluoromethylstyrene;

[0038] The third solvent is selected from at least one of propylene glycol methyl ether acetate, ethyl lactate, ethylene glycol monomethyl ether, and cyclohexanone.

[0039] To achieve the fourth objective, the technical solution adopted by this invention is as follows:

[0040] An adhesive coating comprising a resist film and a substrate, wherein the composition described in any one of the preceding claims is spin-coated onto the substrate to form the resist film.

[0041] Furthermore, the thickness of the resist film is uniform.

[0042] Furthermore, the thickness of the resist film is 80–200 nm.

[0043] Furthermore, the substrate is selected from any one of silicon, glass, quartz, copper, tantalum, gold, aluminum, polyimide, alumina, and ceramic.

[0044] To achieve the fifth objective, the technical solution adopted by this invention is as follows:

[0045] The method for forming the pattern involves sequentially subjecting the adhesive coating described in any of the above-mentioned methods to pre-baking, exposure, post-baking, and development to obtain a photoresist pattern.

[0046] Furthermore, the method for forming the pattern is as follows:

[0047] Pre-baking: Heating removes the solvent to help the resist film adhere evenly to the substrate surface and ensure that the adhesive coating has appropriate hardness and stability, thus improving its smoothness; preferably, the heating equipment used is a horizontal heating plate;

[0048] Exposure: Radiation is applied to the surface of the resist film coated with adhesive. The surface of the formed resist film is irradiated through a predetermined pattern mask. Various radiation sources can be used, including low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, and argon lasers. For example, electromagnetic waves or particle beam radiation can be selected, but it is not limited to these. The radiation type can cover microwaves, infrared rays, visible light, ultraviolet (UV) light, X-rays, gamma rays, electron beams, proton beams, neutron beams, and ion beams. For example, the wavelength of electromagnetic wave radiation can be 365nm ultraviolet light, but it is not limited to this.

[0049] Post-baking: Heating promotes the cross-linking reaction of epoxy groups in the resist film, forming a cross-linked network insoluble in the developer, further removing solvent, reducing the emission of volatiles in the resist coating in subsequent processes, and improving the accuracy and stability of the pattern; preferably, the heating equipment used is a horizontal heating plate;

[0050] Development: The developer dissolves the unexposed (uncrosslinked) resist film, while the resist film in the exposed areas becomes insoluble due to the crosslinking reaction, thus remaining and forming the desired pattern;

[0051] The developer can be selected from an alkaline aqueous solution or an organic solvent. 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 thionamide, cyclohexanone, and methyl ethyl ketone.

[0052] Furthermore, an appropriate amount of water-soluble organic solvent or surfactant can be added to the alkaline aqueous solution as a developer. The water-soluble organic solvent can be methanol or ethanol, but is not limited to these.

[0053] The development method can be selected from immersion development or spray development. Immersion development completely immerses the wafer in the developer solution for a certain period of time to ensure uniform development. Spray development uses a spraying device to evenly spray the developer solution onto the wafer surface, while the wafer rotates to ensure uniform distribution of the developer solution.

[0054] The above-described one or more technical solutions in the embodiments of the present invention have at least one of the following technical effects:

[0055] The present invention provides a photoresist, a preparation method, a composition, a coating layer, and a method for pattern formation. The photoresist has a simple molecular structure and controllable molecular weight; the preparation method is simple, and the compound can be synthesized in only two steps, reducing production costs; the coating layer prepared by the composition using the photoresist as the photoresist component has excellent film-forming properties, the film layer is uniform and dense, chemically stable, and not easily deformed, thus ensuring good performance before use; the pattern formed using the coating layer provided by the present invention has clear pattern lines and high resolution.

[0056] Additional aspects and advantages of the invention will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the invention. Attached Figure Description

[0057] Figure 1The photoresist pattern obtained by spin-coating the composition provided in Example 1 onto a silicon wafer is shown in Example 8 of the present invention.

[0058] Figure 2 The photoresist pattern obtained by spin-coating the composition provided in Example 2 onto a silicon wafer is shown in Example 8 of the present invention. Detailed Implementation

[0059] To make the objectives, technical solutions, and advantages of this invention clearer, the technical solutions of this invention will be clearly and completely described below in conjunction with specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this invention. The following embodiments are used to illustrate this invention, but cannot be used to limit the scope of this invention.

[0060] In the following embodiments, unless otherwise specified, the experimental methods used are conventional methods, and the materials and reagents used are commercially available, unless otherwise specified, and are carried out in accordance with the techniques or conditions described in the literature in this field or in accordance with the product instructions.

[0061] Example 1

[0062] I. Preparation of intermediates.

[0063] Compound 1,3,5-tribromobenzene (0.40 g, 1.29 mmol), pinacol 4-hydroxyphenylboronic acid (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 and stirred to dissolve. Tetra(triphenylphosphine)palladium (20 mg, 0.017 mmol) was added under a nitrogen atmosphere, and the mixture was refluxed in an oil bath at 100 °C for 4 h. The reaction was monitored for completeness by thin-layer chromatography. The reaction solution was cooled to room temperature, and extraction was performed three times consecutively using dichloromethane and saturated sodium chloride aqueous solution as extractants. The organic phase was collected, and water was removed using anhydrous sodium sulfate as a drying agent. After filtration to separate the solid and liquid phases, the organic phase was evaporated to dryness to remove the solvent. The mixture was purified by silica gel adsorption column chromatography using petroleum ether as the eluent to obtain the intermediate. Its 1H NMR spectrum 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).

[0064] II. Preparation of corrosion resist.

[0065] 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 and stirred to dissolve, yielding a reaction solution. The reaction was carried out under nitrogen atmosphere in a 115°C oil bath for 2 hours until the intermediate was completely reacted (thin-layer chromatography was used to monitor the reaction completion). After cooling to room temperature, excess epichlorohydrin was removed by rotary evaporation to obtain the reaction product. 4-methyl-2-pentyl ketone (2 ml) and sodium hydroxide solution (1 mol / L, 1 ml) were added to this product, mixed thoroughly, heated to 90°C, stirred, and refluxed for 2 hours. After cooling to room temperature, the organic and aqueous layers were extracted and separated. The organic matter in the aqueous layer was further extracted with 4-methyl-2-pentyl ketone. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to obtain the crude product. The crude product was recrystallized using 4-methyl-2-pentyl ketone to obtain the photoresist.

[0066] Its 1H magnetic spectrum analysis is as follows: 1 H NMR (500 MHz, CDCl3) δ7.74 (s, 3H), 7.56 - 7.42 (m, 6H), 6.92 - 6.78 (m, 6H), 4.11 (ddd, J = 62.0,11.4, 5.5 Hz, 6H), 3.35 (p, J = 5.7 Hz, 3H), 3.05 (dd, J = 7.2, 5.6 Hz, 3H), 2.77(dd, J = 7.1, 5.5 Hz, 3H).

[0067] III. Preparation of the composition.

[0068] 4g of corrosion resist Dissolved in propylene glycol monomethyl ether acetate

[0069] In a sample of 95.94 g, triphenylsulfonium hexafluoroantimonate (0.04 g), ethylenediamine (0.01 g), and benzophenone (0.01 g) were added as photoacid generators. The mixture was then thoroughly mixed and filtered through a 0.2 μM Teflon membrane to obtain the resist composition.

[0070] Example 2

[0071] In this embodiment, compared to Example 1, the difference lies in the amount of photoacid-producing agent triphenylsulfonium hexafluoroantimonate added during the preparation of the composition being 0.08g, and the amount of propylene glycol monomethyl ether acetate added being 95.90g.

[0072] Example 3

[0073] I. Preparation of intermediates.

[0074] Compound 3,3',5,5'-tetrabromobenzene (0.61 g, 1.29 mmol), pinacol ester of 3,5-dihydroxyphenylboronic acid (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 to dissolve, and under a nitrogen atmosphere, tetra(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 for completeness by thin-layer chromatography.

[0075] The reaction solution was cooled to room temperature, and extraction was performed three times consecutively using dichloromethane and saturated sodium chloride aqueous solution as extractants. The organic phase was collected, dried with anhydrous sodium sulfate, filtered to separate the solid and liquid phases, and then evaporated to dryness to remove the solvent. The organic phase was purified by silica gel adsorption column chromatography using petroleum ether as eluent to obtain the intermediate 1,2,4,5-tetra(3-hydroxyphenyl)benzene.

[0076] Its 1H NMR spectrum analysis is as follows: 1 H NMR (500 MHz, CDCl3) δ10.01 (s, 8H), 7.70 (dd, J = 19.3, 2.1 Hz, 6H), 6.65 (d, J = 1.8 Hz, 8H), 6.21(t, J = 1.8 Hz, 4H).

[0077] II. Preparation of corrosion resist.

[0078] 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 to dissolve, and refluxed at 115°C in an oil bath under a nitrogen atmosphere for 2 h until the intermediate was completely reacted (the reaction was monitored by thin-layer chromatography). After cooling to room temperature, excess epichlorohydrin was removed by rotary evaporation to obtain the reactant. 4-methyl-2-pentyl ketone (2 ml) and sodium hydroxide solution (1 mol / L, 1 ml) were added to the reactant, mixed thoroughly, heated to 90°C, stirred, and refluxed for 2 h. After cooling to room temperature, the organic and aqueous layers were separated by extraction, and the organic matter in the aqueous layer was further extracted with 4-methyl-2-pentyl ketone. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to obtain the crude product. The crude product was recrystallized using 4-methyl-2-pentyl ketone to obtain the photoresist.

[0079] Its 1H NMR spectrum analysis is as follows: 1 H NMR (500 MHz, CDCl3)δ 7.46 (s, 6H), 7.06 (d, J = 2.3 Hz, 8H), 6.42 (t, J = 2.2 Hz, 4H), 4.13 (ddd, J =48.5, 11.4, 5.5 Hz, 16H), 3.35 (p, J = 5.7 Hz, 8H), 3.05 (dd, J = 7.2, 5.6 Hz, 8H), 2.82 (dd, J = 7.3, 5.5 Hz, 8H).

[0080] III. Preparation of the composition.

[0081] 5g of corrosion resist Dissolved in ethyl lactate (94.50 g), then added photoacid-generating agent triphenylsulfonium hexafluoroantimonate (0.10 g), acid diffusion control agent ethylenediamine (0.02 g), and photoinitiator benzophenone (0.02 g), mixed evenly, and filtered through a 0.2 μM Teflon membrane to obtain the resist composition.

[0082] Example 4

[0083] I. Preparation of intermediates.

[0084] Compound 1,3,5-tribromobenzene (0.40 g, 1.29 mmol), pinacol ester of 3,5-dihydroxyphenylboronic acid (1.37 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 to dissolve, and under a nitrogen atmosphere, tetra(triphenylphosphine)palladium (20 mg, 0.017 mmol) was added. The mixture was refluxed in an oil bath at 100 °C for 4 h, and the reaction was monitored for completeness by thin-layer chromatography.

[0085] The reaction solution was cooled to room temperature, and extraction was performed three times consecutively using dichloromethane and saturated sodium chloride aqueous solution as extractants. The organic phase was collected, and water was removed using anhydrous sodium sulfate as a drying agent. After filtration to separate the solid and liquid phases, the organic phase was evaporated to dryness to remove the solvent. The mixture was then purified by silica gel adsorption column chromatography using petroleum ether as the eluent to obtain the intermediate. Its 1H NMR spectrum 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).

[0086] II. Preparation of corrosion resist.

[0087] intermediate (0.80 g, 2 mmol), imidazole (6.8 mg, 0.1 mmol), and epichlorohydrin (5.55 g, 60 mmol) were added to a 100 mL Schlenk reaction flask and stirred to dissolve, yielding a reaction solution. The reaction was carried out under nitrogen atmosphere in a 115°C oil bath for 2 hours until the intermediate was completely reacted (the reaction was monitored for completeness by thin-layer chromatography). After cooling to room temperature, excess epichlorohydrin was removed by rotary evaporation to obtain the reactant. 4-methyl-2-pentyl ketone (2 ml) and sodium hydroxide solution (1 mol / L, 1 ml) were added to the reactant, mixed thoroughly, heated to 90°C, stirred, and refluxed for 2 hours. After cooling to room temperature, the organic and aqueous layers were extracted and separated. The organic matter in the aqueous layer was further extracted with 4-methyl-2-pentyl ketone. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to obtain the crude product. The crude product was recrystallized using 4-methyl-2-pentyl ketone to obtain the photoresist.

[0088] Its 1H NMR spectrum analysis is as follows: 1H 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).

[0089] III. Preparation of the composition.

[0090] corrosion resist Dissolved in propylene glycol monomethyl ether acetate (94.95 g), the photoacid-generating agent triphenylsulfonium hexafluoroantimonate (0.10 g), the acid diffusion control agent ethylenediamine (0.02 g), and the photoinitiator benzophenone (0.02 g) were added and mixed evenly. After filtration through a 0.2 μM Teflon membrane, the resist composition was obtained.

[0091] Example 5

[0092] I. Preparation of intermediates.

[0093] Compound 3,3',5,5'-tetrabromobiphenyl (0.61 g, 1.29 mmol), pinacol 4-hydroxyphenylboronic acid (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 and stirred to dissolve. Tetra(triphenylphosphine)palladium (20 mg, 0.017 mmol) was added under a nitrogen atmosphere, and the mixture was refluxed in an oil bath at 100 °C for 4 h. The reaction was monitored for completeness by thin-layer chromatography. The reaction solution was cooled to room temperature, and extraction was performed three times consecutively using dichloromethane and saturated sodium chloride aqueous solution as extractants. The organic phase was collected, and water was removed using anhydrous sodium sulfate as a drying agent. After filtration to separate the solid and liquid phases, the organic phase was evaporated to dryness to remove the solvent. The mixture was purified by silica gel adsorption column chromatography using petroleum ether as the eluent to obtain the intermediate.

[0094] Its 1H NMR spectrum analysis is as follows: 1H 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).

[0095] II. Preparation of corrosion resist.

[0096] 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. The reaction was carried out under nitrogen atmosphere in a 115°C oil bath for 2 h until the intermediate was completely reacted (thin-layer chromatography was used to monitor the reaction completion). After cooling to room temperature, excess epichlorohydrin was removed by rotary evaporation to obtain the reaction product. 4-methyl-2-pentyl ketone (2 ml) and sodium hydroxide solution (1 mol / L, 1 ml) were added to this product, mixed thoroughly, heated to 90°C, stirred, and refluxed for 2 h. After cooling to room temperature, the organic and aqueous layers were extracted and separated. The organic matter in the aqueous layer was further extracted with 4-methyl-2-pentyl ketone. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to obtain the crude product. The crude product was recrystallized using 4-methyl-2-pentyl ketone to obtain the photoresist.

[0097] Its 1H NMR spectrum analysis is as follows: 1 H NMR (500 MHz, CDCl3) δ7.73 - 7.64 (m, 6H), 7.55 - 7.43 (m, 8H), 6.96 - 6.78 (m, 8H), 4.09 (ddd, J =67.1, 11.4, 5.6 Hz, 8H), 3.35 (p, J = 5.7 Hz, 4H), 3.05 (dd, J = 7.2, 5.6 Hz, 4H), 2.77 (dd, J = 7.1, 5.5 Hz, 4H).

[0098] III. Preparation of the composition.

[0099] 4g of corrosion resist Dissolved in ethyl lactate (95.89 g), the photoacid-generating agent triphenylsulfonium hexafluoroantimonate (0.09 g), the acid diffusion control agent ethylenediamine (0.01 g), and the photoinitiator benzophenone (0.01 g) were added and mixed evenly. After filtration through a 0.2 μM Teflon membrane, the resist composition was obtained.

[0100] Example 6

[0101] The difference between this embodiment and Example 3 is that the content of each component in the resist composition is different. 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.

[0102] Example 7

[0103] The difference between this embodiment and Example 4 is that the content of each component in the composition is different. 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.

[0104] The compositions provided in Examples 1 to 7 exhibited similar properties in terms of photosensitivity, line edge roughness, and initial weight loss temperature T. loss The results are shown in Table 1:

[0105]

[0106] Example 8

[0107] The process for preparing the photoresist pattern is as follows: The composition is spin-coated onto a 1cm layer using a spin coater at a speed of 2000 rpm. 2 On a silicon wafer, a photoresist coating is formed by pre-baking at 60°C for 2 minutes on a horizontal heating plate. Then, the wafer is irradiated through a photomask using a photolithography machine. After exposure, the wafer is immediately post-baked at 90°C for 1 minute on a horizontal heating plate. Then, the wafer is developed in methyl isobutyl ketone organic solvent for 30 seconds by immersion development. Finally, the wafer is rinsed with isopropanol for 10 seconds to obtain a photoresist pattern.

[0108] In this case, the composition prepared in Example 1 was spin-coated onto a silicon wafer to obtain a photoresist pattern, such as... Figure 1 As shown;

[0109] The composition prepared in Example 2 was spin-coated onto a silicon wafer to obtain a photoresist pattern, as shown below. Figure 2 As shown.

[0110] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and not to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some of the technical features; and these modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A corrosion resist, characterized in that, The structural formula is selected from any of the following structural formulas: or .

2. A method for preparing a photoresist, characterized in that, For preparing the resist as described in claim 1, when the structural formula of the resist is... The process includes the following steps: S100, Add to compound 3,3',5,5'-tetrabromobiphenyl The base I and the first solvent are stirred and dissolved, then the catalyst is added. The reaction is carried out at 80℃~120℃ for 2~6 hours to obtain the intermediate. ; S200. The intermediate, base II and the second solvent are added to the reaction system, stirred and dissolved, and reacted at 50℃~80℃ for 1h~5h under an inert gas atmosphere to obtain the corrosion resist. When the structural formula of the corrosion resist is The process includes the following steps: S100, Add to compound 3,3',5,5'-tetrabromobiphenyl The base I and the first solvent are stirred and dissolved, then the catalyst is added. The reaction is carried out at 80℃~120℃ for 2~6 hours to obtain the intermediate. ; S200. The intermediate, base II and the second solvent are added to the reaction system, stirred and dissolved, and reacted at 50℃~80℃ for 1h~5h under an inert gas atmosphere to obtain the corrosion resist.

3. The method for preparing the resist according to claim 2, characterized in that, 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 tetra(triphenylphosphine)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 epichlorohydrin.

4. A composition, characterized in that, Including the resist as described in claim 1, the composition comprises, by weight percentage, the following components: Corrosion resist 0.1-10%; Photoacid-producing agent 0.01-1%; Acid diffusion control agent 0-0.1%; Photoinitiator 0.01–1%; The remainder is a third solvent.

5. The composition according to claim 4, characterized in that, The photo-induced acid-producing agent is triphenylsulfonium hexafluoroantimonate; The acid diffusion control agent is selected from at least one of n-octylamine, tri-n-octylamine, N-methyldi-n-octylamine, tert-octylamine, triethylamine, and ethylenediamine; The photoinitiator is benzophenone; The third solvent is selected from at least one of propylene glycol methyl ether acetate, ethyl lactate, ethylene glycol monomethyl ether, and cyclohexanone.

6. An adhesive coating, characterized in that, The composition as described in claim 4 is spin-coated onto the substrate to form the resist film, which includes a resist film and a substrate.

7. The adhesive coating as described in claim 6, characterized in that, The thickness of the resist film is 80–200 nm.

8. The adhesive coating as described in claim 6, characterized in that, The substrate is made of any one of silicon, glass, quartz, copper, tantalum, gold, aluminum, polyimide, alumina, and ceramic.

9. A method for forming a pattern, characterized in that, The adhesive coating as described in claim 6 is subjected to pre-baking, exposure, post-baking and development processes in sequence to obtain a photoresist pattern.

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