Sulfonium sulfonate salt photoacid generator synthesized from patchouli alcohol and synthesis method for sulfonium sulfonate salt photoacid generator

The technology of a photoacid generator and patchouli alcohol is applied in the fields of sulfonate preparation, organic chemical methods, photosensitive materials for opto-mechanical equipment, etc. Simple synthesis route and reduced effect of transparency

Pending Publication Date: 2020-05-12
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

However, the existing photoacid generators still have the problem of acid diffusion, which makes it impossible to reduce the edge roughness

Method used

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  • Sulfonium sulfonate salt photoacid generator synthesized from patchouli alcohol and synthesis method for sulfonium sulfonate salt photoacid generator
  • Sulfonium sulfonate salt photoacid generator synthesized from patchouli alcohol and synthesis method for sulfonium sulfonate salt photoacid generator
  • Sulfonium sulfonate salt photoacid generator synthesized from patchouli alcohol and synthesis method for sulfonium sulfonate salt photoacid generator

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] This embodiment provides a kind of sulfonate salt photoacid generator synthesized by patchouli alcohol, the reaction scheme of the synthetic method of this photoacid generator is as follows:

[0041]

[0042] It specifically includes the following steps:

[0043] S1. Sodium hydroxide (14g, 350mmol) was dissolved in water (60g) to form a 30% sodium hydroxide solution; methyl fluorosulfonyl difluoroacetate (20g, 104mmol) was added to ice water (200g) , to obtain the reaction solution, and slowly add 30% sodium hydroxide solution prepared under stirring into the above-mentioned reaction solution, after the addition, the reaction solution was stirred for 2.5 hours in an ice bath (controlling the temperature below 10 degrees Celsius), Then continue to stir at room temperature for 1 hour, start heating, make the temperature rise to 95 degrees Celsius in 30 minutes, and stir at 95 degrees Celsius for 3 hours, stop heating, cool to room temperature, neutralize with hydrochlo...

Embodiment 2

[0048] This embodiment provides a kind of sulfonate salt photoacid generator synthesized by patchouli alcohol, the reaction scheme of the synthetic method of this photoacid generator is as follows:

[0049]

[0050] It specifically includes the following steps:

[0051] S1. Under nitrogen protection at 0°C, pyridine (18g, 228mmol), bis(trichloromethyl)carbonate (9g, 30mmol) was added to dichloromethane (400g), and patchouli was slowly added under stirring Aroma alcohol 2-1 (20g, 90mmol) to obtain a reaction solution; then, the reaction solution was stirred at room temperature for 3 hours, and then 1,1-difluoro-2-hydroxyl-ethanesulfonic acid sodium salt (17g, 92mmol) Added to the reaction solution, stirred for 10 hours, the reaction solution was concentrated under vacuum to obtain a mixture, the mixture was filtered to obtain a solid, the solid was washed with acetonitrile three times, the acetonitrile solution was collected, the collected acetonitrile solution was concentra...

Embodiment 3

[0054] This embodiment provides a kind of sulfonate salt photoacid generator synthesized by patchouli alcohol, the reaction scheme of the synthetic method of this photoacid generator is as follows:

[0055]

[0056] It specifically includes the following steps:

[0057] S1. Under nitrogen at 0°C, sodium hydride (3.4g, 141mmol) was slowly added to a mixture of patchouli alcohol 3-1 (20g, 90mmol) and anhydrous tetrahydrofuran (300g), and stirred for 20 minutes; then , Ethyl bromoacetate (15.3g, 92mmol) was added dropwise to the above mixture, and stirred for 20 minutes; then, stirred at 25°C for 6 hours for reaction, after the reaction was completed, quenched with water at 0°C. Concentrate the quenched mixture by rotary evaporation, extract three times with ethyl acetate (200g×3), combine the extracts, wash with saturated brine (300g), dry over anhydrous sodium sulfate, and concentrate by rotary evaporation to obtain the crude product ; The crude product was purified by colu...

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Abstract

The invention discloses a sulfonium sulfonate salt photoacid generator synthesized from patchouli alcohol and a synthesis method for the sulfonium sulfonate salt photoacid generator, belonging to thefields of chemical synthesis and photoetching materials. The photoacid generator has a structural general formula which is described in the specification. In the structural general formula, R1 is oneselected from the group consisting of groups which are described in the specification; and R2 is one selected from the group consisting of an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocycloalkyl group, an ester group-containing alkyl group and a fluorine-containing alkyl group. The synthesis method for the photoacid generator comprises the following steps: allowing the patchouli alcohol to react with a sulfonate compound so as to obtain an intermediate; allowing the intermediate to react with (cyclohexyl-1,5-dienyloxy)-trimethyl-silane, tetramethylene sulfoxide and trifluoroacetic anhydride so as to obtain the sulfonium sulfonate salt photoacid generator. According to the invention, a raw material, namely the patchouli alcohol adopted in the method provided by the invention has large molecular weight, so the photoacid generator formed by the patchouli alcohol also has large molecular weight; diffusion of the photoacid generator can be reduced; and improvement of theedge roughness, reduction of the line width roughness and improvement of the resolution ratio are facilitated.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and photolithography materials, in particular to a sulfonate sulfonium salt photoacid generator synthesized from patchouli alcohol 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] The development of lithography technology is inseparable from the development of lithography materials, and the development of lithography materials determines the development and application of lithography technology to a certain extent. Photolithographic materials (especially photoresist), also known as photoresist, are the most critical functio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/10C07C303/32C07C309/12C07C309/17G03F7/004
CPCC07B2200/07C07C303/32C07C309/12C07C309/17C07C2601/08C07C2603/70C07D333/10G03F7/004
Inventor 喻珍林蒋小惠李嫚嫚潘惠英王尹卓
Owner 上海博栋化学科技有限公司
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