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Sulfonium onium salt photoacid generator containing patchouli alcohol structure, and preparation method thereof

A technology of photoacid generator and patchouli alcohol, which is applied in the field of photoresist to achieve the effect of improving solubility, low diffusivity and improving resolution

Inactive 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 patchouli alcohol structure and preparation method thereof, to solve the existing onium salt photoacid generator proposed in the above-mentioned background technology still has the problem of acid Diffusion problem

Method used

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  • Sulfonium onium salt photoacid generator containing patchouli alcohol structure, and preparation method thereof
  • Sulfonium onium salt photoacid generator containing patchouli alcohol structure, and preparation method thereof
  • Sulfonium onium salt photoacid generator containing patchouli alcohol structure, and preparation method thereof

Examples

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Embodiment 1

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

[0028] 1) Add patchouli alcohol 1-1 (0.225mol, 50g), sodium salt of difluorosulfoacetic acid (0.227mol, 45g) and p-toluenesulfonic acid monohydrate (0.026mol, 5g) into toluene (500g) , heated to reflux for 18 hours and cooled to room temperature to obtain a mixture; the mixture was filtered 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 The mixed solution was collected and the filter cake was dried to obtain the sulfonate compound 1-2 (0.162mol, 65g, yield 71.8%) containing patchouli alcohol structure.

[0029] 2) The sulfonate compound 1-2 (0.159mol, 60g) and triphenylsulfonium bromide (0.151mol, 52g) obtained in step 1) containing the patchouli alcohol structure were dissolved in dichloromethane ( 300...

Embodiment 2

[0033] A sulfonium salt photoacid generator 2-3 containing a patchouli alcohol structure, the specific synthesis steps are as follows:

[0034] 1) Patchouli alcohol 2-1 (0.225mol, 50g), 2-sulfoacetate sodium salt (0.228mol, 37g) and p-toluenesulfonic acid monohydrate (0.026mol, 5g) were added to toluene (500g ), 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 was filtered, The dried filter cake was collected to obtain the sulfonate compound 2-2 (0.172mol, 63g, 76.5%) containing patchouli alcohol structure.

[0035] 2) The sulfonate compound 2-2 (0.163mol, 60g) containing the patchouli alcohol structure obtained in step 1) and three (4-methylphenyl) sulfonium chloride (0.164mol, 56g) Dissolved in a mixed solvent of dichloromethane (400g) and w...

Embodiment 3

[0039] A sulfonium salt-based photoacid generator 3-3 containing a patchouli alcohol structure, the specific synthesis steps are as follows:

[0040] 1) Under nitrogen protection at 0°C, add pyridine (0.569mol, 45g), bis(trichloromethyl)carbonate (0.078mol, 23g) into dichloromethane (2000g) and stir, then slowly add patchouli alcohol 3-1 (0.225mol, 50g); the reaction mixture was stirred at 25°C for 3 hours; then 1,1-difluoro-2-hydroxyl-ethanesulfonic acid sodium salt (0.228mol, 89g) was added to the reaction solution, Stir for 10 hours; concentrate by rotary evaporation to obtain a mixture, filter the mixture to obtain a solid, and wash the solid three times with acetonitrile; concentrate the mixed acetonitrile solution, and add it to methyl tert-butyl ether for beating, filter the above mixture, collect and dry The filter cake was dried to obtain the sulfonate compound 3-2 (0.162mol, 70g, yield 72.0%) containing patchouli alcohol structure.

[0041] 2) The sulfonate compound...

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Abstract

The invention relates to the technical field of photoresist, and concretely discloses a sulfonium onium salt photoacid generator containing a patchouli alcohol 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, 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 C1-12 alkyl group. The photoacid generator prepared by the invention has good hydrophilicity, has an improved solubility in an organic solvent, and can effectively inhibit the diffusion of acids. The patchouli alcohol is used as a reaction initiator to react and then reacts with sulfonium halide to obtain the sulfonium onium salt photoacid generator containing the patchouli alcohol structure. The preparation method of the sulfoniumonium salt photoacid generator containing the patchouli alcohol structure 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 patchouli 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 photo...

Claims

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Application Information

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IPC IPC(8): C07C303/22C07C309/06C07C381/12G03F7/004
CPCC07C303/22C07C309/06C07C381/12C07C2603/70G03F7/004
Inventor 郭颖蒋小惠毕景峰李嫚嫚
Owner 上海博栋化学科技有限公司
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