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Star-shaped ArF photoresist film-forming resin, preparation method thereof and photoresist composition

A film-forming resin and photoresist technology, which is applied in the field of semiconductor photoresist microelectronic chemistry, can solve the problems of photoresist formula screening and shaping, achieve good film-forming properties, reduce the diffusion range of photoacid, and improve The effect of sensitivity

Active Publication Date: 2021-08-06
广东粤港澳大湾区黄埔材料研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the screening and shaping of photoresist formulations is a world-class problem

Method used

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  • Star-shaped ArF photoresist film-forming resin, preparation method thereof and photoresist composition
  • Star-shaped ArF photoresist film-forming resin, preparation method thereof and photoresist composition
  • Star-shaped ArF photoresist film-forming resin, preparation method thereof and photoresist composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] In the state full of nitrogen, 10g methacrylate cholate (monomer 1, formula II), 20g methacrylate butyrolactone (monomer 2, formula III), 10g methacrylate sulfonium salt ester (mono 3, formula IV), 60g adamantyl methacrylate (monomer 4, formula V), 2mmol (1.45g) initiator (formula VII), 8mmol CuBr, 8mmol PMEDTA and 200mL dioxane were added to a 500mL reaction In the bottle, stir well; then, add 1 g of dimethylethylaminomethacrylate (monomer 5, formula VI) and stir well. The reaction system was heated to 80°C for 5 hours. It was then cooled to room temperature, precipitated in ether, filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in methanol, filtered, and the filter cake was dried. This process was repeated twice to obtain a crude film-forming resin. The crude product was dissolved in tetrahydrofuran containing EDTA, passed through an ion-exchange resin column five times to remove copper ions, precipitated, filt...

Embodiment 2

[0036] In the state full of nitrogen, 30g acrylate cholate (monomer 1, formula II), 10g acrylate butyrolactone (monomer 2, formula III), 5g acrylate sulfonium salt ester (monomer 3, formula IV) , 55g adamantyl acrylate (monomer 4, formula V), 4mmol (2.9g) initiator (formula VI), 16mmol CuBr, 16mmol PMEDTA and 200mL dioxane join in the reaction bottle of 500mL, fully stir; Then, Add 5 g of dimethylethylaminomethacrylate (monomer 5, formula VI) and stir thoroughly. The reaction system was heated to 110° C. for 3 hours. It was then cooled to room temperature, precipitated in ether, filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in methanol, filtered, and the filter cake was dried. This process was repeated twice to obtain a crude film-forming resin. The crude product was dissolved in tetrahydrofuran containing EDTA, passed through an ion-exchange resin column five times to remove copper ions, precipitated, filtered, and d...

Embodiment 3

[0038] In the state filled with nitrogen, 10g methacrylate cholate (monomer 1, formula II), 10g acrylate butyrolactone (monomer 2, formula III), 10g methacrylate sulfonium salt ester (monomer 3 , formula IV), 70g adamantyl methacrylate (monomer 4, formula V), 3mmol (2.17g) initiator (formula VI), 12mmol CuBr, 12mmol PMEDTA and 200mL methyl ethyl ketone were added to a 500mL reaction flask , fully stirred; then, added 0.5g dimethyl ethyl amino methacrylate (monomer 5, formula VI) and fully stirred. The reaction system was heated to 90°C for 5 hours. It was then cooled to room temperature, precipitated in ether, filtered, and the filter cake was dried. The filter cake was dissolved in tetrahydrofuran, precipitated in methanol, filtered, and the filter cake was dried. This process was repeated twice to obtain a crude film-forming resin. The crude product was dissolved in tetrahydrofuran containing EDTA, passed through an ion-exchange resin column five times to remove copper ion...

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Abstract

The invention discloses star-shaped ArF photoresist film-forming resin, a preparation method thereof and a photoresist composition. The film-forming resin comprises a random polymer structure as shown in the following formula I, wherein n, m, x, y and z are mole ratios of monomers, n is more than 0 and less than or equal to 0.3, m is more than 0 and less than or equal to 0.8, x is more than 0 and less than or equal to 0.2, y is more than 0 and less than or equal to 0.3, and n+m+x+y is equal to 1; and R1, R2, R3, R4 and R5 are H, CH3 or CH2CH3. The photoresist composition comprises the film-forming resin and an organic solvent, the film-forming resin accounts for 5-30%, and the balance is the organic solvent. A photoacid generator and an acid diffusion inhibitor are introduced into the film-forming resin at the same time, so that the photoacid diffusion range can be well reduced, and the sensitivity and the resolution of the photoresist are improved.

Description

technical field [0001] The invention belongs to the technical field of semiconductor photoresist microelectronic chemistry, and relates to a star-shaped resin used for photoresist, a preparation method thereof, and a photoresist composition. Background technique [0002] Photoresist, also known as photoresist, refers to an etching-resistant film material whose solubility changes under the irradiation or radiation of ultraviolet light, electron beam, ion beam, X-ray, etc. Photoresist occupies a special position in the manufacturing process of integrated circuit chips. The higher the integration level of integrated circuits, the higher the requirements for photoresist. [0003] According to the Rayleigh equation, the use of a short-wavelength light source in the photolithography process can improve the resolution of the photoresist. The light source wavelength of the photolithography process has developed from 365nm (I-line) to 248nm (KrF), 193nm (ArF), 13nm (EUV). In order ...

Claims

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Application Information

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IPC IPC(8): G03F7/004
CPCG03F7/004
Inventor 季生象李小欧刘亚栋顾雪松
Owner 广东粤港澳大湾区黄埔材料研究院