A kind of bio-based arf photoresist film-forming resin, photoresist composition and preparation method thereof

A film-forming resin and photoresist technology, applied in the field of semiconductor photoresist microelectronic chemistry, can solve the problems of photoresist formula screening and shaping problems, and achieve the effects of good adhesion and improved film-forming ability.

Active Publication Date: 2022-04-12
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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  • A kind of bio-based arf photoresist film-forming resin, photoresist composition and preparation method thereof
  • A kind of bio-based arf photoresist film-forming resin, photoresist composition and preparation method thereof
  • A kind of bio-based arf photoresist film-forming resin, photoresist composition and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In the state full of nitrogen, 10g methacrylate cholate (monomer 1, formula II), 60g adamantyl methacrylate (monomer 2, formula III), 20g methacrylate butyrolactone (monomer 3 , formula IV), 10g sulfonium methacrylate (monomer 4, formula V) and 600mL dioxane were added to a 1000mL reaction flask, and then 0.5g azobisisobutyronitrile (AIBN) was added to fully Stir and heat to 60°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 75 g of film-forming resin. GPC records the weight-average molecular weight M of the film-forming resin w It is 18000, and the molecular weight distribution PDI is 1.25.

[0030]

Embodiment 2

[0032] In the state full of nitrogen, 30g acrylate cholate (monomer 1, formula II), 55g adamantyl acrylate (monomer 2, formula III), 10g acrylate butyrolactone (monomer 3, formula IV), 5g Add sulfonium acrylate (monomer 4, formula V) and 600mL dioxane into a 1000mL reaction flask, then add 0.3g azobisisobutyronitrile (AIBN), stir well, heat to 60°C, keep 8 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 80 g of film-forming resin. GPC records the weight-average molecular weight M of the film-forming resin w It is 22000, and the molecular weight distribution PDI is 1.3.

Embodiment 3

[0034] In the state full of nitrogen, 10g methacrylate cholate (monomer 1, formula II), 70g adamantyl acrylate (monomer 2, formula III), 10g methacrylate butyrolactone (monomer 3, formula IV), 10g of sulfonium methacrylate (monomer 4, formula V) and 600mL of methyl ethyl ketone were added to a 1000mL reaction flask, then 0.3g of azobisisobutyronitrile (AIBN) was added, and fully stirred , heated to 50°C and maintained for 12 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 80 g of film-forming resin. GPC records the weight-average molecular weight M of the film-forming resin w It is 15000, and the molecular weight distribution PDI is 1.37.

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Abstract

The invention discloses a bio-based ArF photoresist film-forming resin, a photoresist composition and a preparation method thereof, comprising a random copolymer structure as shown in formula I, wherein n, m, x and y are monomers Mole ratio, 0<n≤0.3, 0<m≤0.8, 0<x≤0.2, 0<y≤0.3, n+m+x+y=1; R 1 , R 2 , R 3 and R 4 for H, CH 3 or CH 2 CH 3 . A photoresist composition, comprising 5-30% of the film-forming resin, 0.5-10% of an acid diffusion inhibitor, and the rest being an organic solvent. The photoacid generating agent of the invention can not only generate acid in the exposed area, but also effectively and evenly distribute in the photoresist, and improve the film-forming ability of the photoresist. The prepared photoresist has good adhesion and sensitivity ≤ 38mJ / cm 2 , The resolution can reach below 90nm.

Description

technical field [0001] The invention belongs to the technical field of semiconductor photoresist microelectronic chemistry, and relates to a film-forming resin for photoresist, a photoresist composition and a preparation method. 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 to improve th...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C08F220/18C08F220/28C08F220/32C08F220/38G03F7/004
CPCC08F220/1811G03F7/004C08F220/283C08F220/32C08F220/38
Inventor季生象刘亚栋李小欧顾雪松
Owner广东粤港澳大湾区黄埔材料研究院