Sulfonium sulfonate salt photoacid generator synthesized from beta-cineole, and synthesis method thereof

A technology of photoacid generator and synthesis method, which is applied in the fields of sulfonate preparation, photosensitive materials for optomechanical equipment, organic chemistry, etc., can solve the problem of inability to reduce edge roughness, etc. Line width roughness, the effect of increasing fat solubility

Pending Publication Date: 2020-05-08
上海博栋化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing photoacid generators still have the problem ...

Method used

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  • Sulfonium sulfonate salt photoacid generator synthesized from beta-cineole, and synthesis method thereof
  • Sulfonium sulfonate salt photoacid generator synthesized from beta-cineole, and synthesis method thereof
  • Sulfonium sulfonate salt photoacid generator synthesized from beta-cineole, and synthesis method thereof

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Embodiment 1

[0038] This embodiment provides a kind of sulfonate salt photoacid generator synthesized by beta-eucalyptol, the reaction scheme of the synthetic method of this photoacid generator is as follows:

[0039]

[0040] It specifically includes the following steps:

[0041] S1. Sodium hydroxide (12.8g, 325mmol) was dissolved in water (30g) to form a solution; methyl fluorosulfonyl difluoroacetate (20g, 104mmol) was added to ice water (50g) to obtain a reaction solution, And under stirring, the prepared sodium hydroxide solution was slowly added to the above 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), and then continued to stir for 1 hour at room temperature. After that, start heating, make the temperature rise to 95 degrees centigrade in 30 minutes, and stir at 95 degrees centigrade for 3 hours, stop heating, cool to room temperature, neutralize with hydrochloric acid...

Embodiment 2

[0046]This embodiment provides a kind of sulfonate salt photoacid generator synthesized by beta-eucalyptol, the reaction scheme of the synthetic method of this photoacid generator is as follows:

[0047]

[0048] It specifically includes the following steps:

[0049] S1, under nitrogen protection at 0°C, pyridine (27g, 341mmol), bis(trichloromethyl)carbonate (13.5g, 34mmol) was added to methylene chloride (800g), and beta was slowly added under stirring - Eucalyptol (30g, 135mmol) 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 (25g, 136mmol) 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 mixed acetonitrile solution was concentrated, and added to methyl tert-butyl ether for beat...

Embodiment 3

[0052] This embodiment provides a kind of sulfonate salt photoacid generator synthesized by beta-eucalyptol, the reaction scheme of the synthetic method of this photoacid generator is as follows:

[0053]

[0054] It specifically includes the following steps:

[0055] S1. Under nitrogen at 0°C, sodium hydride (5g, 208mmol) was slowly added to a mixture of beta-eucalyptol 3-1 (30g, 135mmol) and anhydrous tetrahydrofuran (400g), and stirred for 20 minutes; Then, ethyl 2-bromo-2-cyclopentyl acetate (32g, 136mmol) was added dropwise to the above mixture, and stirred for 20 minutes; then, stirred at 25°C for 6 hours to react, after the reaction was completed, °C, quenched with water. Concentrate the quenched mixture by rotary evaporation, extract three times with dichloromethane (250g×3), combine the extracts, wash with saturated brine (200g), dry over anhydrous sodium sulfate, and concentrate by rotary evaporation to obtain the crude product ; The crude product was purified b...

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Abstract

The invention discloses a sulfonium sulfonate salt photoacid generator synthesized from beta-cineole, and a synthesis method thereof, and belongs to the field of chemical synthesis and photoetching materials. The structural general formula of the photoacid generator is shown in the description; and in the formula, R1 is one of three formulas also shown in the description, and R2 is one of an alkylgroup, a naphthenic base, an ester group-containing alkyl group and a fluorine-containing alkyl group. The synthesis method of the photoacid generator comprises the following steps: reacting beta-cineole with a sulfonate compound to obtain an intermediate; and reacting the intermediate with (cyclohexyl-1,5-dienyloxy)-trimethyl-silane, tetramethylene sulfoxide and trifluoroacetic anhydride to obtain the sulfonium sulfonate photoacid generator. The beta-cineole used as the raw material has a high molecular weight, and the photoacid generator formed by the beta-cineole also has a high molecularweight, so that the diffusion of the photoacid generator can be reduced, and the improvement of the edge roughness, the reduction of the line width roughness and the 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 beta-eucalyptol 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 functiona...

Claims

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Application Information

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IPC IPC(8): C07D333/46C07C309/17C07C303/32C07C309/06C07C309/12G03F7/004
CPCC07C309/06C07C309/12C07C309/17C07C2602/28C07D333/46G03F7/004
Inventor 潘惠英蒋小惠李嫚嫚毕景峰贺宝元
Owner 上海博栋化学科技有限公司
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