Photoresist resin monomer with adamantane structure and synthesis method thereof

A technology of resin monomer and synthesis method, applied in the field of photoresist resin monomer of adamantane structure and its synthesis, can solve the problem of poor T-top pattern, insufficient hydrophobicity of photoresist, affecting the resolution of photoresist, etc. problem, to achieve the effect of excellent etching resistance, excellent anti-swelling performance, and improved resolution

Inactive Publication Date: 2021-04-20
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

[0004] The photoresist has insufficient hydrophobicity, and water easily enters the photoresist, causing the expansion of the photoresist pattern, resulting in a T-top bad pattern, which greatly affects the resolution of the photoresist
193nm mostly adopts resins with acrylate or methacrylate structures, which are more transparent than resins with styrene structures, but have weaker etching resistance

Method used

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  • Photoresist resin monomer with adamantane structure and synthesis method thereof
  • Photoresist resin monomer with adamantane structure and synthesis method thereof
  • Photoresist resin monomer with adamantane structure and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] The first step: 1,3-diacetyl-5-adamantanol (5g, 21mmol) was dissolved in tetrahydrofuran (50mL), triethylamine (6.4g, 63mmol) was added, cooled to 0 degrees Celsius with ice water, Under the protection of nitrogen, a solution of acryloyl chloride (2g, 22mmol) in tetrahydrofuran (20mL) was slowly added dropwise thereto, the reaction solution rose to room temperature and continued to react for 5 hours, the reaction solution was concentrated under vacuum to remove the solvent, and ethyl acetate (50mL) was added , adding saturated aqueous sodium bicarbonate (10mL), separating the organic phase, extracting the aqueous phase three times with ethyl acetate (50mL×3), combining the organic phases, washing the organic phase with saturated brine, drying over anhydrous sodium sulfate, and concentrating to obtain the compound 1-2 (5.5 g, 19 mmol, yield: 89.5%).

[0028] The second step: 1,1,1,3,3,3-hexafluoro-2-isopropanol (5.7g, 38mmol) was added to anhydrous tetrahydro...

Embodiment 2

[0031]

[0032] The raw material is the intermediate compound 1-3 of Example 1, compound 1-3 (10g, 16mmol), ion exchange resin (CAS: 39389-20-3) (1g), acetone (4.7g, 81mmol) are added to toluene (120mL), stirred at 60°C for 12 hours, filtered to remove the ion exchange resin, concentrated and purified by column chromatography to obtain compound P2 (5.1g, 7.5mmol, yield: 47.1%).

Embodiment 3

[0034]

[0035] The raw material is the intermediate compound 1-3 of Example 1, compound 1-3 (10g, 16mmol), ion exchange resin (CAS: 39389-20-3) (1g), 1-cyclohexylacetaldehyde (9g, 80mmol ) was added to toluene (150mL), stirred and reacted at 60 degrees Celsius for 12 hours, filtered to remove the ion exchange resin, concentrated and purified by column chromatography to obtain compound P3 (5.3g, 6.5mmol, 40.7%).

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PUM

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Abstract

The invention discloses a photoresist resin monomer with an adamantane structure, and relates to the field of photoresist resin. The structural formula of the resin monomer is shown in the specification, wherein R1 and R2 are respectively independently alkane with 1-10 carbon atoms, R1 and R2 can be combined through a covalent bond to form a cyclic structure, and R3 is hydrogen or methyl. The resin monomer contains the adamantane structure and has excellent etching resistance; due to excellent swelling resistance, the resolution of a photoetching pattern is improved, and the generation of T-top is inhibited; and the material has very high transparency at 193 nm, and is especially suitable for photoetching operation at 193 nm.

Description

technical field [0001] The invention relates to the field of photoresist resins, in particular to a photoresist resin monomer with an adamantane structure and a synthesis method thereof. Background technique [0002] Photolithography technology refers to the process of transferring the pattern designed on the mask plate to the substrate by using the chemical sensitivity of photoresist under the action of visible light, ultraviolet light, electron beam, etc., through exposure, development, etching and other processes. Graphics microfabrication technology. [0003] 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. This type of material is photochemically sensitive. , After photochemical reaction, its solubility in developer solution changes. According to different photochemical reaction mechanisms, phot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06G03F7/027G03F7/004
Inventor 王尹卓郭颖李嫚嫚潘惠英贺宝元
Owner 上海博栋化学科技有限公司
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