Photoinduced acid generator with diphenyl sulfonium structure and synthesis method of photoinduced acid generator

A technology of a photoacid generator and a synthesis method, which is applied in the field of photoresist and can solve the problems of photoresist swelling, resolution reduction, increase in line width and roughness of photolithography pattern, etc.

Pending Publication Date: 2021-06-08
华衍化学(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The acid diffusion after photoacid generator exposure is an important factor affecting the performance of the photoresist. The increase of acid diffusion usually leads to the increase of the line width and roughness of the p

Method used

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  • Photoinduced acid generator with diphenyl sulfonium structure and synthesis method of photoinduced acid generator
  • Photoinduced acid generator with diphenyl sulfonium structure and synthesis method of photoinduced acid generator
  • Photoinduced acid generator with diphenyl sulfonium structure and synthesis method of photoinduced acid generator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Bis(4-hydroxyphenyl)iodonium bromide 1-1 (20g, 50.9mmol) was added to a mixed solvent of DMF (100mL) and water (50ml), sodium hydroxide (7.2g, 180mmol) was added, stirred After 10 minutes, add a solution of A-1 (36g, 102.2mmol) in DMF (60mL) dropwise, react at room temperature for 6 hours after the dropwise addition, and adjust the pH to 5-6 with 2mol / L dilute hydrochloric acid after cooling in ice water , extracted with 440 mL of a mixed solvent of dichloromethane / methanol (10:1), combined the organic phases, washed the organic phase with 50 mL of 2mol / L dilute hydrochloric acid, washed with 50 mL of saturated brine, dried over anhydrous sodium sulfate and concentrated to obtain 31.8 g Crude intermediate 1-2.

[0028] Add intermediate 1-2 (31.8g) to chlorobenzene (250mL), add 2-(phenylthio)ethanol A-2 (6.5g, 42.1mmol), stir at 25°C for half an hour, add copper benzoate (0.3g), raised to 110°C, stirred and reacted at 110°C for 2 hours, added deionized water...

Embodiment 2

[0031]

[0032] The first two steps are the same as in Example 1.

[0033] The third step: Intermediate B-1 (11.4g, 29.5mmol) and dicyclohexylcarbodiimide (3.1g, 15mmol) were added to dichloromethane (120mL), and carbonyldiimidazole was added under stirring at 0°C (2.4g, 14.8mmol), stirred at 0°C for one hour, continued to warm up to room temperature and stirred for 30 minutes, the reaction solution was filtered, and the filtrate was concentrated to obtain a solid. The solid and intermediate 2-1 (15g, 29.6mmol) were added to acetonitrile (120mL), stirred and reacted for 3 hours, added deionized water (50mL), extracted three times with dichloromethane (100mL×3), combined organic After the phase was concentrated under vacuum, n-hexane (200 mL) was added and the temperature was raised to 50 degrees Celsius, cooled for recrystallization, filtered, and dried to obtain photoacid generator 2-2 (19.4 g, yield 84.9%).

Embodiment 3

[0035]

[0036] The first two steps are the same as in Example 1.

[0037] The third step: Intermediate C-1 (11.1g, 29.7mmol) and dicyclohexylcarbodiimide (3.1g, 15mmol) were added to dichloromethane (120mL), and carbonyldiimidazole was added under stirring at 0°C (2.4g, 14.8mmol), stirred at 0°C for one hour, continued to warm up to room temperature and stirred for 30 minutes, the reaction solution was filtered, and the filtrate was concentrated to obtain a solid. The solid and Intermediate 3-1 (15g, 29.6mmol) were added to acetonitrile (120mL), stirred and reacted for 3 hours, deionized water (50mL) was added, extracted three times with dichloromethane (100mL×3), and the combined organic After the phase was concentrated under vacuum, n-hexane (200 mL) was added and the temperature was raised to 50 degrees Celsius, cooled for recrystallization, filtered, and dried to obtain photoacid generator 3-2 (19.6 g, yield 87.1%).

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PUM

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Abstract

The invention discloses a photoacid generator with a diphenyl sulfonium structure and a synthesis method of the photoacid generator, and relates to the field of photoresists, the photoacid generator has the following structure shown in the description, wherein A is C1-C5 fluoroalkane, and B is a naphthenic base of C3-C10. The photoacid generator disclosed by the invention can control acid diffusion, reduce line width roughness, prevent pattern damage and form photoetching patterns with uniform sizes, and has high transparency under a 193nm light source.

Description

technical field [0001] The invention relates to the field of photoresists, in particular to a photoacid generator and a synthesis method thereof. Background technique [0002] Photoacid generator is an important component of photoresist. Under the irradiation of light or radiation of specific wavelength, it can generate acid, and use the generated acid to trigger reactions such as deprotection or crosslinking of acid-sensitive groups in photoresist. Occurrence, so that the exposed area and the non-exposed area have a polarity difference, and the photolithographic pattern can be obtained after being developed by the developer. [0003] The acid diffusion after exposure of the photoacid generator is an important factor affecting the performance of the photoresist. The increase of the acid diffusion usually leads to the increase of the line width and roughness of the photolithographic pattern and the decrease of the resolution. The poor alkali solubility of the photoresist may...

Claims

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Application Information

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IPC IPC(8): C07C381/12G03F7/004
CPCC07C381/12G03F7/004C07C2603/74C07C2602/42C07C2601/14
Inventor 张猛王巧玲
Owner 华衍化学(上海)有限公司
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