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Sulfonium onium salt photoacid generator containing beta-eudesmol structure, and preparation method thereof

A technology of photoacid generator and eucalyptol, which is applied in the field of photoresist, can solve the problems of acid diffusion, achieve low diffusivity, simple synthesis process, and favorable effects for imaging

Inactive 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

[0005] The object of the present invention is to provide a kind of sulfonium salt photoacid generator containing β-cineole structure, to solve the existing onium salt photoacid generator proposed in the above-mentioned background technology still exists the diffusion of acid question

Method used

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  • Sulfonium onium salt photoacid generator containing beta-eudesmol structure, and preparation method thereof
  • Sulfonium onium salt photoacid generator containing beta-eudesmol structure, and preparation method thereof
  • Sulfonium onium salt photoacid generator containing beta-eudesmol structure, and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0027] A sulfonium salt photoacid generator 1-3, the specific synthesis steps are as follows:

[0028] 1) β-cineole 1-1 (45.0mmol, 10g), p-methoxyphenol (0.8mmol, 0.1g), difluorosulfoacetic acid sodium salt (44.9mmol, 8.9g) and p-toluenesulfonic acid A mixture of monohydrate (5.2 mmol, 1 g) was heated to reflux in toluene (150 g) for 18 hours and cooled to room temperature; the mixture was filtered and the solid was washed three times with acetonitrile; the combined acetonitrile solution was then concentrated and added to methyl Beat in tert-butyl ether, filter and collect the dried filter cake to obtain solid sulfonate compound 1-2 containing β-cineole structure (38.8mmol, 15.6g, yield 86.2%).

[0029] 2) The sulfonate compound 1-2 (37.3mmol, 15g) and triphenylsulfonium bromide (37.3mmol, 12.8g) obtained in step 1) containing β-eucalyptol structure were dissolved in di In a mixed solvent of methyl chloride (100g) and water (100g); the mixture was stirred at 30°C for 24 hours...

Embodiment 2

[0033] A kind of sulfonium salt photoacid generator 2-3, concrete synthetic steps are as follows:

[0034] 1) β-cineole 2-1 (45.0mmol, 10g), p-methoxyphenol (0.8mmol, 0.1g), 2-sulfoacetate sodium salt (45.0mmol, 7.3g), p-toluene A mixture of sulfonic acid monohydrate (5.2 mmol, 1 g) was heated to reflux in toluene (150 g) for 18 hours and cooled to room temperature; the mixture was filtered and the solid was washed three times with acetonitrile; the combined acetonitrile solution was then concentrated and added to Slurry was performed in methyl tert-butyl ether, filtered and dried filter cake was collected to obtain solid sulfonate compound 2-2 (39.0mol, 14.3g, 86.8%) containing β-cineole structure.

[0035] 2) The sulfonate compound 2-2 (38.2mmol, 14g) containing the β-cineole structure obtained in step 1) and tri(4-methylphenyl)sulfonium chloride (38.4mmol, 13.1g) was dissolved in a mixed solvent of dichloromethane (100g) and water (100g); the mixture was stirred at 30°C fo...

Embodiment 3

[0039] A sulfonium salt photoacid generator 3-3, the specific synthesis steps are as follows:

[0040] 1) Under nitrogen protection at 0°C, pyridine (113.8mmol, 9g), bis(trichloromethyl)carbonate (15.2mmol, 4.5g) was added to dichloromethane (200g) and stirred, then slowly added β- Eucalyptol 3-1 (45.0mmol, 30g); the reaction solution was stirred at 25°C for 3 hours; then 1,1-difluoro-2-hydroxyl-ethanesulfonic acid sodium salt (45.1mmol, 8.3g) was added into the reaction solution, stirred for 10 hours; concentrated by rotary evaporation to obtain a mixture, filtered the mixture, washed the solid with acetonitrile three times; then concentrated the mixed acetonitrile solution, added it to methyl tert-butyl ether for beating, filtered The dried filter cake was collected to obtain solid sulfonate compound 3-2 (34.7 mmol, 15 g, yield 77.1%) containing β-eucalyptol structure.

[0041] 2) The sulfonate compound 3-2 (34.7mmol, 15g) and triphenylsulfonium chloride (34.8mmol, 10.4g) o...

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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 beta-cineole structure, and a preparation method thereof. The photoacid generator includes an anion and a cation, the anion and the cation have structures represented by formulas shown in the description; and in the formulas, R represents an alkyl group, acycloalkyl 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 acids. The invention further provides the preparation method of the sulfonium salt photoacid generator containing the beta-cineole structure. Beta-cineole is used as a reaction initiator to react and then reacts with sulfoniumhalide to obtain the sulfonium salt photoacid generator containing the beta-cineole structure, so 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 β-cineole 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 photoacid gen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C381/12C07C309/17C07C309/12C07C303/32G03F7/004
CPCC07C303/32C07C309/12C07C309/17C07C381/12C07C2602/10G03F7/0045
Inventor 潘惠英蒋小惠李嫚嫚郭颖
Owner 上海博栋化学科技有限公司
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