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Sulfonium onium salt photoacid generator containing cedrol structure and preparation method thereof

A technology of photoacid generator, cedar alcohol, applied in the field of photoresist, to reduce edge roughness, increase fat solubility, and have the effect of broad market prospect

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

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of sulfonium salt photoacid generator containing cedrinyl alcohol structure and preparation method thereof, to solve the existing onium salt photoacid generator proposed in the above-mentioned background technology still exists in the diffusion of acid The problem

Method used

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  • Sulfonium onium salt photoacid generator containing cedrol structure and preparation method thereof
  • Sulfonium onium salt photoacid generator containing cedrol structure and preparation method thereof
  • Sulfonium onium salt photoacid generator containing cedrol structure and preparation method thereof

Examples

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Effect test

Embodiment 1

[0032] A sulfonium salt photoacid generator 1-8 containing a cedaryl alcohol structure, the specific synthesis steps are as follows:

[0033] 1) Under nitrogen at 0°C, sodium hydride (1.25mol, 30g) was slowly added to a mixture of cedaryl alcohol 1-1 (0.899mol, 200g) and tetrahydrofuran (2000g), and stirred for 20 minutes; then ethyl bromoacetate Ester 1-2 (0.928mol, 155g) was added dropwise to the above mixture, stirred for 20 minutes; then stirred at 25°C for 6 hours; after the reaction was completed, quenched with water at 0°C; the quenched mixture Concentrate by rotary evaporation, extract with dichloromethane (700g×3); combine the extracts, wash with saturated brine (1000g), dry over anhydrous sodium sulfate, and concentrate by rotary evaporation to obtain a crude product; the crude product is purified by column chromatography to obtain a liquid Cederyl alcohol-containing ester compounds 1-3 (0.778mol, 240g, yield 86.5%).

[0034] 2) The ester compound 1-3 (0.648mol, 200...

Embodiment 2

[0040] A sulfonium salt photoacid generator 2-8 containing a cederyl alcohol structure, the specific synthesis steps are as follows:

[0041]1) Under nitrogen at 0°C, sodium hydride (1.25mol, 30g) was slowly added to a mixture of cedaryl alcohol 2-1 (0.899mol, 200g) and tetrahydrofuran (2000g), and stirred for 20 minutes; then ethyl chloroacetate Ester 2-2 (0.938mol, 115g) was added dropwise to the above mixture, stirred for 20 minutes; then stirred at 25°C for 6 hours; after the reaction was completed, quenched with water at 0°C, and the quenched mixture Concentrate by rotary evaporation, extract with dichloromethane (700g×3); combine the extracts, wash with saturated brine (1000g), dry over anhydrous sodium sulfate, and concentrate by rotary evaporation to obtain a crude product; the crude product is purified by column chromatography to obtain a liquid Cederyl alcohol-containing ester compound 2-3 (0.762mol, 235g, yield 84.7%).

[0042] 2) The ester compound 2-3 (0.648mol, ...

Embodiment 3

[0048] A sulfonium salt photoacid generator 3-8 containing a cederyl alcohol structure, the specific synthesis steps are as follows:

[0049] 1) Under nitrogen at 0°C, sodium hydride (1.25mol, 30g) was slowly added to a mixture of cedaryl alcohol 3-1 (0.899mol, 200g) and tetrahydrofuran (3000g), and stirred for 20 minutes; then 2-bromo - Ethyl 2-cyclopentyl acetate 3-2 (0.915mol, 215g) was added dropwise to the above mixture, stirred for 20 minutes; then stirred at 25°C for 6 hours; after the reaction was completed, quenched with water at 0°C The quenched mixed solution was concentrated by rotary evaporation and extracted with dichloromethane (700g×3); the combined extracts were washed with saturated brine (1000g), dried over anhydrous sodium sulfate, and concentrated by rotary evaporation to obtain a crude product; The product was purified by column chromatography to obtain a liquid ester compound 3-3 (0.717mol, 270g, yield 79.7%) containing cederyl alcohol structure.

[005...

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Abstract

The invention relates to the technical field of photoresist, and particularly discloses a sulfonium salt compound containing a cedrol structure, a preparation method of the sulfonium salt compound, aphotoacid generator and an application of the photoacid generator. The sulfonium onium salt compound containing the cedrol structure comprises anions and cations, the anion and the cation each have astructure in which R1 and R2 each independently represent an alkyl group, a cycloalkyl group, a heteroalkyl group, or a heterocycloalkyl group, and P1, P2, and P3 each independently represent a hydrogen atom or an optionally substituted alkyl group having 1 to 12 carbon atoms. The photoacid generator prepared by the invention has good hydrophilicity, can improve the solubility in an organic solvent, and can effectively inhibit the diffusion of acid. According to the preparation method provided by the invention, the sulfonium onium salt compound containing the cedrol structure is obtained by reacting the sulfonic acid compound containing the cedrol structure with the sulfonium halide, and the preparation method is simple.

Description

technical field [0001] The invention relates to the technical field of photoresists, in particular to a sulfonium salt photoacid generator containing a cedaryl alcohol structure and a preparation method thereof. Background technique [0002] Photoacid generators, also called photoacid generators, are light-sensitive compounds that decompose under light to produce acids, which can cause acid-sensitive resins to decompose or cross-link, so that the light-emitting parts and non-irradiated parts The irradiated part dissolves in the developing solution and increases the contrast, which can be used in the technical field of graphic microprocessing. [0003] Among them, photoacid generators are widely used in imaging systems such as chemically amplified resists (also known as photoresists). Commonly used photoacid generators include diazonium salt compounds, onium salt compounds, nitrogen hydroxysulfonate compounds, etc. Among them, onium salt compounds are very important photoac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/004C07C303/32C07C309/12C07C381/12
CPCG03F7/004C07C303/32C07C381/12C07C67/31C07C51/09C07C2603/97C07C2601/08C07C309/12C07C69/708C07C59/13
Inventor 郭颖潘惠英喻珍林李嫚嫚
Owner 上海博栋化学科技有限公司
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