Photoresist resin monomer synthesized from carboxylic acid compound and synthesis method thereof

A technology of carboxylic acid compound and resin monomer, applied in the field of photoresist resin monomer and its synthesis, can solve the problem of low resolution of photolithography pattern, and achieve improved resolution, increased etching resistance, and increased solubility Effect

Inactive Publication Date: 2020-05-05
上海博栋化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, due to the specific structure of the acid-sensitive resin monomer in the existing photoresist, there is a problem of low photolithographic pattern resolution

Method used

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  • Photoresist resin monomer synthesized from carboxylic acid compound and synthesis method thereof
  • Photoresist resin monomer synthesized from carboxylic acid compound and synthesis method thereof
  • Photoresist resin monomer synthesized from carboxylic acid compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] This embodiment provides a kind of photoresist resin monomer synthesized by carboxylic acid compound, the reaction scheme of the synthetic method of this resin monomer is as follows:

[0035]

[0036] It specifically includes the following steps:

[0037] S1. Dissolve vinyl glycol ether (Formula 1-1, 9.3g, 105.5mmol) and triethylamine (10.7g, 105.7mmol) in dichloromethane (200g) to obtain a mixed solution; Acryloyl chloride (10 g, 95.7 mmol) was added dropwise to the above mixture, stirred at 0° C. for 30 minutes under nitrogen protection, and continued stirring at room temperature for 4 hours after the reaction was completed. Filtrate and concentrate the filtrate to obtain a crude product, which was purified by column chromatography to obtain a colorless liquid intermediate (Formula 1-2, 12 g, 76.8 mmol, yield 80.3%).

[0038] S2, intermediate (12g, 76.8mmol), 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylic acid (8.6g, 38.0mmol) and p-tert-butylcatechol ( 0.5g, 3.0...

Embodiment 2

[0040] This embodiment provides a kind of photoresist resin monomer synthesized by carboxylic acid compound, the reaction scheme of the synthetic method of this resin monomer is as follows:

[0041]

[0042] It specifically includes the following steps:

[0043] S1. Dissolve 1-vinyloxy-propan-2-ol (Formula 2-1, 10.8g, 105.7mmol) and triethylamine (10.7g, 105.7mmol) in dichloromethane (200g) to obtain a mixed solution ; Next, methacryloyl chloride (10g, 95.7mmol) was added dropwise to the above mixture, stirred at 0°C for 30 minutes under nitrogen protection, and continued to stir for 4 hours at room temperature after the reaction was completed. Filtrate and concentrate the filtrate to obtain a crude product, which was purified by column chromatography to obtain a colorless liquid intermediate (Formula 2-2, 13.5 g, 79.3 mmol, yield 82.9%).

[0044] S2, intermediate (13.5g, 79.3mmol), 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylic acid (8.8g, 38.9mmol) and p-tert-butylcatech...

Embodiment 3

[0046] This embodiment provides a photoresist resin monomer synthesized by a carboxylic acid compound, and the synthesis method of the resin monomer specifically includes the following steps:

[0047] S1, 1-vinyloxy-propan-2-ol (105.7mmol) and triethylamine (105.7mmol) were dissolved in dichloromethane (200g) to obtain a mixed solution; then, methacryloyl chloride (84.56mmol ) was added dropwise to the above mixture, stirred at 0° C. under nitrogen protection for 30 minutes, and continued to stir for 4 hours at room temperature after the reaction was completed. Filtrate and concentrate the filtrate to obtain a crude product, which is purified by column chromatography to obtain a colorless liquid intermediate.

[0048] S2. After mixing the intermediate (70.2mmol), 2,5-dioxobicyclo[2.2.2]octane-1,4-dicarboxylic acid (39mmol) and p-tert-butylcatechol (3.0mmol) , and placed under the condition of 75° C. and stirred for 1.5 hours, and then distilled under reduced pressure to obtai...

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PUM

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Abstract

The invention discloses a photoresist resin monomer synthesized from a carboxylic acid compound and a synthesis method of the photoresist resin monomer, and belongs to the field of chemical synthesisand photoetching materials. The structural general formula of the resin monomer is shown in the specification, wherein R is linear chain or branched chain alkyl. The synthesis method of the resin monomer comprises the following steps: carrying out esterification reaction on a vinyl ether alcohol compound and an acrylic acid compound to obtain an intermediate; and carrying out a reaction on the intermediate and 2, 5-dioxobicyclo[2.2. 2]octane-1, 4-dicarboxylic acid to generate the photoresist resin monomer. The resin monomer provided by the invention comprises an acetal structure and polycyclicand polyester structures, can prevent diffusion of a photoacid generator, improve edge roughness, increase contrast and improve resolution, has excellent etching resistance and fat solubility, and issimple and convenient in preparation method.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and photoresist materials, in particular to a photoresist resin monomer synthesized from carboxylic acid compounds and a synthesis method thereof. Background technique [0002] Photolithography technology refers to the chemical sensitivity of photoresist materials (especially photoresist) under the action of visible light, ultraviolet rays, electron beams, etc., through exposure, development, etching and other processes, the design on the mask plate Graphics microfabrication technology that transfers graphics to the substrate. [0003] Photolithographic materials (especially photoresist), also known as photoresist, are the most critical functional chemical materials involved in photolithography technology. The main components are resin, photoacid generator, and corresponding additives and Solvents, such materials are chemically sensitive to light (including visible light, ultraviolet rays, elec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/757C07C67/04G03F7/004
CPCC07C69/757G03F7/004C07C2602/44
Inventor 郭颖潘惠英喻珍林蒋小惠王尹卓
Owner 上海博栋化学科技有限公司
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