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Degradable resin monomer synthesized from 1, 6-dioxaspiro [2.5] octane and preparation method thereof

A technology of resin monomer and octane, which is applied in the field of degradable resin monomer and its preparation, and can solve the problem of low resolution of photolithographic patterns

Inactive Publication Date: 2021-05-14
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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  • Degradable resin monomer synthesized from 1, 6-dioxaspiro [2.5] octane and preparation method thereof
  • Degradable resin monomer synthesized from 1, 6-dioxaspiro [2.5] octane and preparation method thereof
  • Degradable resin monomer synthesized from 1, 6-dioxaspiro [2.5] octane and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] The preparation of resin monomer compound 1-2:

[0030] Under nitrogen protection, 1,6-dioxaspiro[2.5]octane 1-1 (2g, 17.5mmol) was dissolved in dimethylformamide (20g), after dissolving, 1,8-diazepine was added Bicyclo[5.4.0]undec-7-ene (0.5 g, 3.3 mmol) and methacrylic anhydride (8.1 g, 52.5 mmol) were then stirred at 120° C. for 12 hours. The reaction solution was extracted with ether to obtain an extract, which was washed with water and concentrated to obtain resin monomer 1-2 (2.4 g, 8.9 mmol, molar yield 51.0%).

Embodiment 2

[0032]

[0033] Preparation of compound 2-2: Dissolve glycolic acid 2-1 (2g, 26.3mmol), triethylamine (2.7g, 26.7mmol) in dichloromethane (20g), and then form Acryloyl chloride (2.8 g, 26.7 mmol) was added dropwise to the above mixture, stirred for 30 minutes, and then continued to stir at room temperature for 4 hours. Add water, adjust the pH, extract to obtain an organic phase, and concentrate to obtain a crude product, which is purified by column chromatography to obtain compound 2-2 (3 g, 20.8 mmol, molar yield 79.1%).

[0034] Preparation of Compound 2-3: Under nitrogen protection, 1,6-dioxaspiro[2.5]octane (2g, 17.5mmol) was dissolved in dimethylformamide (20g), after dissolution, 1,8 - Diazabicyclo[5.4.0]undec-7-ene (0.5g, 3.3mmol) and compound 2-2 (2.6g, 18.0mmol), stirred at 120°C for 5 hours. The reaction solution was extracted with ether to obtain an extract, which was washed with water and concentrated, and the concentrate was added to hexane for recrystallizat...

Embodiment 3

[0037]

[0038] Preparation of Compound 3-2: 4-Hydroxycyclohexanecarboxylic acid 3-1 (4g, 27.7mmol), triethylamine (3g, 29.6mmol) were dissolved in dichloromethane (40g), then at 0°C, under nitrogen protection Add methacryloyl chloride (3 g, 28.7 mmol) dropwise to the above mixture, stir for 30 minutes, and then continue stirring at room temperature for 4 hours. Add water, adjust the pH, extract the organic phase, and concentrate to obtain the crude product, which is purified by column chromatography to obtain compound 3-2 (4.7 g, 22.1 mmol, molar yield 79.8%).

[0039] Preparation of Compound 3-3: Under nitrogen protection, 1,6-dioxaspiro[2.5]octane (2g, 17.5mmol) was dissolved in dimethylformamide (60g), after dissolution, 1,8- Diazabicyclo[5.4.0]undec-7-ene (0.5g, 3.3mmol) and compound 3-2 (3.8g, 17.9mmol) were stirred at 120°C for 5 hours. The reaction solution was extracted with ether to obtain an extract, which was washed with water and concentrated, and the concentr...

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Abstract

The invention belongs to a degradable photoresist resin monomer, and discloses a degradable resin monomer synthesized from 1, 6-dioxaspiro [2.5] octane and a preparation method thereof. The structural formula of the resin monomer is shown in the specification, and R is a linking bond or a linking group. The preparation method comprises the step of carrying out ring opening esterification on 1, 6-dioxaspiro [2.5] octane to generate the resin monomer. The resin monomer provided by the invention comprises a tert-butyl structure and a cyclic polyester structure, has improved edge roughness, increased contrast ratio and improved resolution ratio, and has excellent etching resistance and fat solubility, and the preparation method is simple and convenient.

Description

technical field [0001] The invention relates to the field of degradable photoresist resin monomers, in particular to a degradable resin monomer synthesized from 1,6-dioxaspiro[2.5]octane and a preparation method thereof. Background technique [0002] 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, electron beams, etc.), and their solubility in the developer solution changes through photochemical reactions. [0003] The resin used in the photoresist is a polymer formed by the copolymerization of various resin monomers. Among them, the acid-sensitive resin monomer is an important part of realizing the difference in the dissolution of the resin in the developer solution ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/10G03F7/027G03F7/004
CPCC07D309/10G03F7/027G03F7/004
Inventor 傅志伟毕景峰潘惠英李嫚嫚
Owner 上海博栋化学科技有限公司
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