Photoacid generator containing double onium salt structure, preparation method and photoresist composition

A technology of photoacid generator and onium salt, which is applied in the field of photoresist, can solve the problem of low acid production efficiency and achieve high acid production 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] In view of this, it is necessary to provide a photoacid generator containing a bis-onium salt structure to solve the technical problem of low acid generation efficiency of existing photoacid generators

Method used

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  • Photoacid generator containing double onium salt structure, preparation method and photoresist composition
  • Photoacid generator containing double onium salt structure, preparation method and photoresist composition
  • Photoacid generator containing double onium salt structure, preparation method and photoresist composition

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preparation example Construction

[0035] In the second aspect, for the above-mentioned photoacid generator, the present invention also provides a preparation method of the photoacid generator. It includes the following steps:

[0036] S11: In a protective gas, diaryl sulfoxide and diaryl sulfide are dissolved in a first organic solvent in a certain ratio in a reactor to obtain a mixed solution, and the reactor is cooled to a certain temperature.

[0037] Wherein the range of the cooling temperature is -30-30°C.

[0038] In a specific embodiment of the present invention, the diaryl sulfoxide is diphenyl sulfoxide, the diaryl sulfide is diphenyl sulfide, and the first organic solvent includes but not limited to dichloromethane, chloroform And one or more of dichloroethane. Diphenyl sulfoxide and diphenyl sulfide were dissolved in dichloromethane in a nitrogen atmosphere, and the temperature was cooled to -30-30°C.

[0039] S12: Add sulfonic anhydride dropwise into the reaction kettle, after a period of reacti...

Embodiment 1

[0082] Example 1: Preparation of a photoacid generator containing a bis-onium salt structure

[0083] S11: Dissolve 21g of diphenyl sulfoxide and 19g of diphenyl sulfide in 300ml of dichloromethane, put them into a reactor filled with nitrogen, and lower the temperature of the reactor to -15°C

[0084] S12, add 29 g of trifluoromethanesulfonic anhydride dropwise to the above-mentioned reaction kettle, and the dropping time is 30 minutes, react for 3 hours, add 200ml of pure water to stop the reaction, cool the temperature of the reaction kettle to room temperature, separate the liquid to take the organic phase, remove Dissolved to constant weight, washed twice with 50ml of diethyl ether to obtain 22g of compound A.

[0085] Its reaction formula is as follows:

[0086]

[0087] S13, 86g of compound A was dissolved in 50g of methanol, 33g of sodium perfluorobutanesulfonate was dissolved in 50g of methanol, 20g of sodium p-toluenesulfonate was dissolved in 50g of methanol, st...

Embodiment 2

[0091] Embodiment two: prepare film-forming resin

[0092] S21, add 45g of monomer 1, 50g of monomer 2, and 20g of monomer 3 into a reactor filled with nitrogen, add 60g of ethyl acetate into the reactor, stir evenly to obtain a mixture of monomers, and then heat up the reactor to At 77°C, mix 10g of ethyl acetate and 12g of benzoyl peroxide to obtain a mixed liquid of the initiator, drop the mixed liquid of the initiator into the reactor of the mixed liquid of the monomer, and react at 77°C for 7 hours , stop the reaction, and the reactor temperature is cooled to room temperature.

[0093] S22, add 600g of methanol into the reaction kettle lowered to room temperature, and after 1 hour of producing the first precipitate, drain the liquid in the reaction kettle, and then add 70g of ethyl acetate into the reaction kettle until the first precipitate dissolves.

[0094] S23, add 600g of methanol into the reaction kettle, after the second precipitate is generated, export the liqui...

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Abstract

The invention discloses a photoacid generator containing a double onium salt structure. The photoacid generator has a structural general formula (I) shown in the specification, in the formula, n is equal to 0 or 1 or 2, and R1-R6 is one or more of H, alkyl with 1-20 carbon atoms, aryl or substituent groups containing sulfur/oxygen/nitrogen heteroatoms; and the M-anions and the Q-anions are sulfonic acid anions. Compared with a photoacid generator with a single onium salt structure, the photoacid generator with the double onium salt structure has higher acid generation efficiency and can be suitable for light sources with various wavelengths.

Description

technical field [0001] The invention belongs to the technical field of photoresists, and in particular relates to a photoacid generator containing a bisium salt structure, a preparation method and a photoresist composition. Background technique [0002] Photoresist composition is one of the key materials in the field of integrated circuit manufacturing, and its main component is a light-sensitive mixed liquid composed of film-forming resin, photosensitizer, acid inhibitor and solvent. Under the irradiation of ultraviolet light, deep ultraviolet light, electron beam, ion beam and other light or radiation, the solubility of the components changes, and after being treated with an appropriate developer, the soluble part is dissolved to obtain the final desired photoresist image. [0003] As a photosensitive component in photoresists, photoacid generators play an important role in photochemical reactions. Therefore, improving the acid-generating efficiency of the photoacid gener...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C321/30C07C319/20C07C303/32C07C309/04C07C309/30G03F7/004
CPCC07C321/30C07C309/04C07C309/30G03F7/0045Y02P20/55
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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