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Molecular glass photoresist of metallocene compound and preparation method thereof

A metallocene compound and molecular glass technology, applied in the field of photoresist, can solve the problems of easy collapse of high-precision lines, increase of line edge roughness, residual exposure area, etc., achieve good dissolution inhibition effect, improve solubility contrast, structure regular effect

Pending Publication Date: 2022-05-06
南通林格橡塑制品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually, in order to meet the anti-etching standard, the resin structure usually contains macromolecule anti-etching groups with ester ring structure, such as adamantane compound, norbornane and other structures, but when rigid structural groups are introduced into the polymer, in During the development process, resin solubility problems are likely to occur, resulting in small residues in the exposure area and irregular jagged edges on the lines; and because the film-forming resin has a large relative molecular mass and a wide molecular weight distribution, high-precision lines are easy to collapse, increasing In addition, most of the photoresist monomer raw materials are controlled by chemical giants in Japan, Germany and the United States, so the use of imported monomers to synthesize photoresist cannot solve the bottleneck from the source question

Method used

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  • Molecular glass photoresist of metallocene compound and preparation method thereof
  • Molecular glass photoresist of metallocene compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 95.2g (about 0.22 mol) of tert-butyl lithocholic acid represented by formula (IV) and 31g (about 0.1 mol) of 1, 1 Ferrocenedicarboxylic acid chloride was dissolved in 2000 ml of anhydrous tetrahydrofuran; 62 ml of triethylamine was slowly added dropwise while stirring to produce precipitation; after 20 hours of reaction, it was quenched with deionized water; extracted 3 times with ethyl acetate; Washing with brine; drying over anhydrous magnesium sulfate, the solution was filtered and concentrated, and vacuum-dried to obtain molecular glass film-forming resin 1# represented by formula (VI).

[0026] Formula (IV)

[0027] Formula (V)

[0028] Formula (VI)

Embodiment 2

[0029] Example 2 In a state filled with nitrogen, 97.6g (about 0.21 mol) of tert-butyl cholic acid represented by formula (VII), and 31g (about 0.1 mol) of 1,1 Dissolve ferrocenedicarboxylic acid chloride in 2000 ml of anhydrous tetrahydrofuran; slowly add 62 ml of triethylamine dropwise to produce precipitation while stirring; quench with deionized water after 20 hours of reaction; extract with ethyl acetate three times; Washing; then drying over anhydrous magnesium sulfate, the solution was filtered and concentrated, and vacuum-dried to obtain molecular glass film-forming resin 2# represented by formula (VIII).

[0030] Formula (VII)

[0031] Formula (V)

[0032] Formula (VIII)

Embodiment 3

[0034]Dissolve 58.4 g (about 50 mmol) of 2# film-forming resin obtained in Example 2 and 12.2 g (about 100 mmol) of 4-dimethylaminopyridine in 400 ml of anhydrous tetrahydrofuran, and then add di-tert-butyl carbonic anhydride 32 g (about 147 mmol) was stirred at room temperature for 20 hours, then injected into 4000 ml of deionized water, collected the sediment, washed with sufficient deionized water, dissolved in 400 ml of ethyl acetate, washed with saturated brine; then washed with anhydrous magnesium sulfate After drying, the solution was filtered and concentrated, and vacuum-dried to obtain molecular glass film-forming resin 3# represented by formula (IX), the theoretical replacement rate of t-boc for hydroxyl was 75%. When the molar equivalent ratio of di-tert-butyl dicarbonic anhydride and film-forming resin 2# (metallocene compound-tert-butyl cholate molecular glass) is adjusted to 2~4, the replacement rate of t-boc for hydroxyl groups can be 50 %~100% metallocene compo...

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Abstract

The invention discloses a molecular glass photoresist of a metallocene compound and a preparation method of the molecular glass photoresist, and belongs to the technical field of semiconductor microelectronic chemistry. The molecular glass photoresist contains molecular glass film-forming resin, a photoacid generator (PAG), an auxiliary agent and a solvent. The molecular glass film-forming resin is monomolecular resin which is shown as a formula (I) and takes a metallocene compound as a core and two cholic acid derivatives as branched chains. The molecular glass film-forming resin disclosed by the invention is single in molecular weight and high in glass transition temperature (Tg); the positive photoresist prepared by matching the film-forming resin with a photoacid generator (PAG) can be used in photolithographic processes of 248nm (KrF), 193nm (ArF), extreme ultraviolet (EUV), nanoimprint (NIL), electron beam (EBL) and the like. In addition, the core raw materials, namely the metallocene compound and the cholic acid derivative, adopted by the invention are all derived from homemade, so that the clamping problem of the semiconductor photoresist and the raw materials thereof can be thoroughly solved from the source.

Description

technical field [0001] The invention relates to a photoresist used in a VLSI chip, in particular to a photoresist using a single beam of deep ultraviolet (DUV) light as an exposure light source, and belongs to the technical field of semiconductor microelectronic chemistry. 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. In recent years, with the trend of miniaturization, light weight and portability of electronic and electrical products, the integration of VLSI chips is getting higher and higher, and the wavelength of light sources for photolithography exposure of semiconductor chips is constantly shortening, from 365nm (i-line) Developed to 248nm (KrF), (ArF), 13nm (EUV). In order to improve the sensitivity of photoresists, the current mainstream KrF, ArF, and EUV photoresists all use chemi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/004C07J9/00
CPCG03F7/004C07J9/005
Inventor 曾伟
Owner 南通林格橡塑制品有限公司
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