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Polymerizable double onium salt structure-containing photoacid generator, preparation method and photoresist

A photoacid generator, polymerized technology, applied in the field of photoresist, can solve the problems of limited absorption wavelength and low acid generation efficiency of photoacid generator, achieve uniform distribution, improve line width and roughness, and achieve high yield. The effect of acid efficiency

Active Publication Date: 2021-04-02
NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The embodiment of the present invention provides a novel polymerizable photoacid generator monomer containing a double onium salt structure, aiming at solving the photoacid generator monomer with a single onium salt structure The problem of low acid production efficiency and limited absorption wavelength of acid generators

Method used

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  • Polymerizable double onium salt structure-containing photoacid generator, preparation method and photoresist
  • Polymerizable double onium salt structure-containing photoacid generator, preparation method and photoresist
  • Polymerizable double onium salt structure-containing photoacid generator, preparation method and photoresist

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preparation example Construction

[0034] see figure 1 , The preparation method of the polymerizable photoacid generator containing bis-onium salt structure according to one embodiment of the present invention comprises the following steps:

[0035] Step S1: preparing a photoacid generator monomer containing a bis-onium salt structure, including the following steps:

[0036] a 1 1. Dissolve the substituted diphenyl sulfoxide and substituted diphenyl sulfide in the first organic solvent in a certain proportion, then place them in a reaction kettle filled with nitrogen, reduce the temperature of the reaction kettle to temperature T, and then add sulfuric acid dropwise Anhydride, react for a period of time t 1 , add water, stop the reaction, then cool the temperature of the reaction kettle to room temperature, extract the organic phase by liquid separation, precipitation to constant weight, and wash the organic phase to obtain compound A, which is the monomer precursor of the photoacid generator. The chemical re...

Embodiment 1

[0077] Preparation of Photoacid Generator Monomer Containing Bisium Salt Structure

[0078] a 1 1. Dissolve 21g of diphenyl sulfoxide and 19g of diphenyl sulfide in 300ml of dichloromethane, then place it in a reactor filled with nitrogen, lower the temperature of the reactor to -15°C, and then add 29g of trifluoromethane dropwise Sulfonic anhydride, dropwise for 3 minutes, react for 3 hours, add 200ml of pure water, stop the reaction, then cool the temperature of the reactor to room temperature, extract the organic phase by liquid separation, precipitate to constant weight, wash twice with 50ml of ether , to obtain 22g compound A, the chemical reaction formula is as follows:

[0079]

[0080] a 2 , Dissolve 86g of compound A, 33g of sodium perfluorobutylsulfonate, 20g of 2-ethanesulfonate sodium methacrylate in 50g of methanol (MeOH), mix and stir for 12 hours, add 50ml of pure water, and continue stirring for 3 hours , precipitation to obtain a turbid water phase, use ...

Embodiment 2

[0092] Preparation of photoresist

[0093] In a clean 100mL glass bottle, add 8.5g of a polymerizable photoacid generator containing a bisium salt structure, 0.06g of a mixed acid with a mass ratio of tert-butylamine and diisobutylamine of 2:8 Diffusion inhibitor, 32g propylene glycol methyl ether acetate, 48g propylene glycol monomethyl ether to obtain a mixture, the mixture was shaken in a bottle in the dark for 24 hours to fully dissolve to obtain a mixed solution. Then, filter the mixed solution successively with 0.22 micron and 0.02 micron nylon and UPE filters, collect the filtrate, and obtain photoresist.

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Abstract

The invention is applicable to the field of photoresists, and provides a polymerizable double onium salt structure-containing photoacid generator which is used for preparing a photoresist. The polymerizable double onium salt structure-containing photoacid generator has the following structural general formula (I), wherein n is an integer greater than or equal to 1; R1-R4 are one or more of H, an alkyl group with 1-20 carbon atoms, an aryl group or a substituent group containing sulfur / oxygen / nitrogen heteroatoms; and the anion M- is a sulfonic acid anion. The polymerizable double onium salt structure-containing photoacid generator has the double onium salt structure, and compared with a photoacid generator with a single onium salt structure, the polymerizable double onium salt structure-containing photoacid generator has high acid generation efficiency and can be suitable for light sources with various wavelengths. The polymerizable double onium salt structure-containing photoacid generator is polymerizable, so that photoresist using the polymerizable double onium salt structure-containing photoacid generator does not need to be additionally added with photoresist resin.

Description

technical field [0001] The invention belongs to the field of photoresists, and in particular relates to a polymerizable photoacid generator containing a bis-onium salt structure, a preparation method of the polymerizable photoacid generator containing a bis-onium salt structure, and the application of the photoacid generator A polymeric photoresist containing a photoacid generator with a double onium salt structure. Background technique [0002] With the research and development of high-integration, ultra-high-speed, ultra-high-frequency integrated circuits and devices, the feature size of large-scale integrated circuits and ultra-large-scale integrated circuits is becoming smaller and smaller. The further development of integrated circuits requires the support of corresponding exposure technologies. Photoresist technology is an important part of exposure technology. A high-performance exposure tool needs a matching high-performance photoresist to truly obtain high-resoluti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C321/30C07C319/20C07C303/32C07C309/04C07C309/12G03F7/004
CPCC07C321/30C07C309/04C07C309/12G03F7/0045C07C2603/70
Inventor 齐国强顾大公毛智彪许从应余绍山许东升
Owner NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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