Photoresist resin monomer synthesized from alpha-cedrene and synthesis method thereof

A technology of resin monomer and synthesis method, which is applied in the field of photoresist resin monomer and its synthesis, can solve the problem of low resolution of photolithographic patterns, and achieve the goals of improving resolution, increasing etch resistance, and increasing dissolution rate Effect

Inactive Publication Date: 2020-04-24
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 alpha-cedrene and synthesis method thereof
  • Photoresist resin monomer synthesized from alpha-cedrene and synthesis method thereof
  • Photoresist resin monomer synthesized from alpha-cedrene and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] This embodiment provides a first intermediate with a structural formula of Formula 1. The reaction route of the synthesis method of the first intermediate is as follows:

[0034]

[0035] It specifically includes the following steps:

[0036] First dissolve α-cedarene (10g, 48.9mmol) in dichloromethane (200g), add 85% mass fraction of m-chloroperoxybenzoic acid (12.9g, 63.7mmol) at 0℃ in an ice water bath Into the above solution, and placed at 25°C and stirred for 8 hours to obtain a reaction solution. Next, filter the reaction solution and use saturated NaHCO sequentially 3 Wash the filtrate with aqueous solution, water and brine, and use anhydrous Na for the organic phase 2 SO 4 After drying and concentration, a solid first intermediate (formula 1, 9 g, 40.8 mmol, molar yield 83.5%) was obtained.

Embodiment 2

[0038] This embodiment provides a photoresist resin monomer synthesized from α-cedarene. The reaction route of the synthesis method of the photoresist resin monomer is as follows:

[0039]

[0040] It specifically includes the following steps:

[0041] Under the protection of nitrogen, the first intermediate (formula 1, 2g, 9.1mmol) provided in Example 1 above was dissolved in dimethylformamide (50g), and after dissolution, 1,8-diazabicyclo[ 5.4.0] Undec-7-ene (0.35 g, 2.3 mmol) and methacrylic anhydride (4.2 g, 27.2 mmol), then stirred at 120°C for 12 hours. The reaction solution was extracted with ether to obtain an extract, and the extract was washed with water and concentrated to obtain a solid photoresist resin monomer (formula 2, 2.2 g, 5.9 mmol, molar yield 64.7%).

Embodiment 3

[0043] This embodiment provides a photoresist resin monomer synthesized from α-cedarene. The reaction route of the synthesis method of the photoresist resin monomer is as follows:

[0044]

[0045] It specifically includes the following steps:

[0046] S1. Dissolve glycolic acid (2g, 26.3mmol) and triethylamine (2.7g, 26.7mmol) in dichloromethane (50g), then add methacrylic acid chloride (2.8g, 26.7mmol) dropwise to the above mixture In the solution, stir for 30 minutes at 0°C under nitrogen protection, and then continue stirring for 4 hours at room temperature. Filter and concentrate the filtrate to obtain a crude product. The crude product is purified by column chromatography to obtain liquid compound 3-1 (Formula 3-1, 3 g, 20.8 mmol, molar yield 79.1%).

[0047] S2, under the protection of nitrogen, the first intermediate (2g, 9.1mmol) provided in the above example was dissolved in dimethylformamide (30g), after dissolution, 1,8-diazabicyclo[5.4. 0] Undec-7-ene (0.35 g, 2.3 mmol...

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PUM

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Abstract

The invention discloses a photoresist resin monomer synthesized from alpha-cedrene and a synthesis method thereof, which belong to the field of chemical synthesis and photoetching materials. The structural general formula of the photoresist resin monomer is shown in the specification, wherein R is a connecting bond or a heteroalkyl group. The synthesis method of the photoresist resin monomer comprises the following steps: reacting alpha-cedrene with peroxide to obtain a first intermediate with an epoxy structure; and carrying out a ring-opening esterification reaction on the first intermediateto obtain the photoresist resin monomer. The photoresist resin monomer provided by the invention comprises a tert-butyl structure and a polycyclic polyester structure, can improve the edge roughness,increase the contrast ratio and improve the resolution ratio, has excellent etching resistance and fat solubility, and is simple and convenient in preparation method.

Description

Technical field [0001] The invention relates to the field of chemical synthesis and photolithography materials, in particular to a photoresist resin monomer synthesized from α-cedarene and a synthesis method thereof. Background technique [0002] Photolithography technology refers to the use of the chemical sensitivity of photolithography materials (specifically photoresist) under the action of visible light, ultraviolet rays, electron beams, etc., through exposure, development, etching and other processes, to design on the mask Graphic microfabrication technology in which the graphic is transferred to the substrate. [0003] Photolithography material (specifically photoresist), also known as photoresist, is the most critical functional chemical material involved in photolithography technology. The main components are resin, photoacid generator, and corresponding additives and Solvents, these materials are chemically sensitive to light (including visible light, ultraviolet rays, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/757C07C67/08G03F7/027
CPCC07C69/757G03F7/027C07C2603/66
Inventor 郭颖毕景峰李嫚嫚喻珍林王尹卓
Owner 上海博栋化学科技有限公司
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