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

A technology of photoacid generator and guaiac alcohol, which is applied in the field of photoresist to achieve good hydrophilic-lipophilic balance, reduce edge roughness, and increase fat solubility

Pending Publication Date: 2020-04-24
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 guaiac alcohol structure and its preparation method, to solve the existing onium salt photoacid generator proposed in the above-mentioned background technology still has acid The problem of diffusion

Method used

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

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Embodiment 1

[0028] A sulfonium salt photoacid generator 1-3, the specific synthesis steps are as follows:

[0029] 1) Guaiacol 1-1 (45.0mmol, 10g), difluorosulfoacetic acid sodium salt (45.4mmol, 9g) and p-toluenesulfonic acid monohydrate (5.2mmol, 1g) were added to toluene (100g) , heated to reflux for 18 hours and cooled to room temperature to obtain a mixture; filtered the mixture to obtain a solid, and the solid was washed three times with acetonitrile; the mixed acetonitrile solution was concentrated and added to methyl tert-butyl ether for beating, filtered The above mixed solution was collected and the filter cake was dried to obtain sulfonate compound 1-2 (31.1 mmol, 12.5 g, yield 69.2%) containing guaiacol structure.

[0030] 2) The sulfonate compound 1-2 (29.8mmol, 12g) and triphenylsulfonium bromide (30.0mmol, 10.3g) obtained in step 1) containing the structure of guaiacol were dissolved in dichloro methane (60g) and water (60g) in a mixed solvent; the mixture was stirred at 3...

Embodiment 2

[0034] A kind of sulfonium salt photoacid generator 2-3, concrete synthetic steps are as follows:

[0035] 1) Guaiacol 2-1 (45.0mmol, 10g), 2-sulfoacetate sodium salt (45.0mmol, 7.3g) and p-toluenesulfonic acid monohydrate (5.2mmol, 1g) were added to toluene (100g), heated to reflux for 18 hours and cooled to room temperature; filtered the mixture to obtain a solid, and the solid was washed three times with acetonitrile; the mixed acetonitrile solution was concentrated, and added to methyl tert-butyl ether for beating, and the above mixed solution, and the dried filter cake was collected to obtain sulfonate compound 2-2 (33.3 mmol, 12.2 g, 74.0%) containing guaiac alcohol structure.

[0036] 2) The sulfonate compound 2-2 (32.7mmol, 12g) containing the guaiacol structure obtained in step 1) and tri(4-methylphenyl)sulfonium chloride (32.9mmol, 11.2 g) be dissolved in a mixed solvent of dichloromethane (80g) and water (80g); the mixture was stirred at 30°C for 24 hours; the reac...

Embodiment 3

[0040] A sulfonium salt photoacid generator 3-3, the specific synthesis steps are as follows:

[0041] 1) Under nitrogen protection at 0°C, add pyridine (11.4mmol, 9g), bis(trichloromethyl)carbonate (15.2mmol, 4.5g) into dichloromethane (400g) and stir, then slowly add guaiac Wood alcohol 3-1 (44.5mmol, 10g); the reaction mixture was stirred at 25°C for 3 hours; then 1,1-difluoro-2-hydroxy-ethanesulfonic acid sodium salt (45.1mmol, 8.3g) was added to the reaction solution, stirred for 10 hours; concentrated by rotary evaporation to obtain a mixture, filtered the mixture to obtain a solid, and washed the solid three times with acetonitrile; concentrated the mixed acetonitrile solution, and added it to methyl tert-butyl ether for beating, and filtered the above mixture , collecting and drying the filter cake to obtain sulfonate compound 3-2 (34.7 mmol, 15 g, yield 77.1%) containing guaiacol structure.

[0042] 2) The sulfonate compound 3-2 (27.7mmol, 12g) and triphenylsulfonium...

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Abstract

The invention relates to the technical field of photoresist, and particularly discloses a sulfonium onium salt photoacid generator containing a guaiol structure and a preparation method thereof. The photoacid generator includes an anion and a cation, the anion and the cation each having a structure in which R represents an alkyl group, a cycloalkyl group, a heteroalkyl group, or a heterocycloalkylgroup, 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 goodhydrophilicity, can improve the solubility in an organic solvent, and can effectively inhibit the diffusion of acid. The invention also provides a preparation method of the sulfonium onium salt photoacid generator, guaiacol is used as a reaction initiator for reaction and then reacts with sulfonium halide to obtain a sulfonium onium salt compound, and the preparation method of the sulfonium oniumsalt photoacid generator is simple.

Description

technical field [0001] The invention relates to the technical field of photoresists, in particular to a guaiac alcohol-containing sulfonium salt photoacid generator 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 photoacid generating...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/17C07C303/32
CPCC07C309/17C07C2602/26
Inventor 郭颖潘惠英喻珍林蒋小惠
Owner 上海博栋化学科技有限公司
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