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Flexible long-chain multi-onium-salt photoacid generating agent, preparation method thereof and photoresist composition

A photoacid generator and photoresist technology, which is applied in the preparation of sulfonic acid, photosensitive materials for optomechanical equipment, mercaptan preparation, etc., can solve the problems that photoresist resin cannot be used

Inactive Publication Date: 2019-05-24
NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing photoacid generators are generally small molecule iodonium salts or sulfonium salts, such as diphenyliodonium hexafluorophosphate, triphenylsulfonium perfluorobutylsulfonate, etc., which cannot be used in The newly developed photoresist resin

Method used

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  • Flexible long-chain multi-onium-salt photoacid generating agent, preparation method thereof and photoresist composition
  • Flexible long-chain multi-onium-salt photoacid generating agent, preparation method thereof and photoresist composition
  • Flexible long-chain multi-onium-salt photoacid generating agent, preparation method thereof and photoresist composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Synthesis of bis(2-bromo-2,2-difluoroethoxy)succinate (3)

[0049] Add 41g of 2-bromo-2,2-difluoroethanol (1), 10g of succinic acid (2), 2.92g of p-toluenesulfonic acid and 90mL of Toluene, the mixture was heated to reflux with stirring for 8h. After the reaction was completed, it was cooled, and the reaction solution was washed three times with 50 mL of sodium carbonate aqueous solution and once with 50 mL of saturated brine, and the organic phase was dried with anhydrous sodium sulfate and concentrated to obtain the esterified product bis(2-bromo-2,2-di Fluoroethoxy) succinate (3) was 21 g in total, and the yield was 61%. NMR results: 1 H NMR (CDCl 3 , δ) 2.69, s, 4H; 4.91, t, 4H.

Embodiment 2

[0050] Example 2: Synthesis of bis(2-sodium sulfonate-2,2-difluoroethoxy)succinate (4)

[0051] In a 500 mL round bottom bottle, add 20 g of bis(2-bromo-2,2-difluoroethoxy)succinate (3) and 80 mL of acetonitrile to dissolve, and stir to dissolve. Under the protection of nitrogen, 17.3g of sodium dithionite, 12.5g of sodium bicarbonate and 80mL of aqueous solution were added dropwise, and the reaction solution was heated and stirred at 70°C for 16h after the addition. Then cool, and add an appropriate amount of solid sodium chloride to saturation. The reaction solution was separated into layers, and the aqueous phase was extracted twice with 30 mL of acetonitrile. The organic phases were combined and transferred to a 500mL round bottom bottle, and 100mL of pure water was added. The mixture was added dropwise with 11.2 g of 30% hydrogen peroxide under nitrogen, and then stirred at room temperature for 16 h. After the reaction, the layers were separated, the aqueous phase was ...

Embodiment 3

[0052] Example 3: Synthesis of triphenylsulfonium chloride salt (5)

[0053] Under nitrogen protection, 9.0 g of diphenyl sulfoxide and 60 mL of anhydrous dichloromethane were added into a 250 mL three-necked flask, and the reaction liquid was cooled to below 0°C. Keeping the reaction liquid below 0°C, 14.5 g of trimethylchlorosilane was added dropwise. After the dropwise addition was completed, the temperature was slowly raised to room temperature, and stirring was continued for 1 h. Then the reaction liquid was cooled down to below 0°C again, and at this temperature, 67 mL of 2M phenylmagnesium chloride in tetrahydrofuran solution was added dropwise. After the dropwise addition was completed, the temperature was slowly raised to room temperature, and stirring was continued for 2 h. Then the reaction solution was quenched with a small amount of water, and 75 mL of 0.2N aqueous hydrochloric acid was added. After the mixture was washed twice with 30 mL of diethyl ether, the ...

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Abstract

The invention discloses a flexible long-chain multi-onium-salt photoacid generating agent, a preparation method thereof and a photoresist composition. The flexible long-chain multi-onium-salt photoacid generating agent has a structural general formula (I) or (II) shown in the description, wherein A is one or both of I and S, X is a chain group having a length of 1-20 atoms, na is 2 or 3, R is oneor any of H, Cl, Br, I, and alkyl group or alkoxy group with a carbon atom number of 1-20, and R has a substitution number of 1-5 on a benzene ring. A carbon chain is extended in a photosensitizer molecule to connect a plurality of onium salt structural units, so that a photosensitizer can be better dissolved in a photoresist solution and can be distributed evenly; the multiple onium salts in themolecule help increase the unit acid generating rate; anions with fluorosulfonic acid have sufficient acidity, and may be subjected to chemical amplification reaction with resin; the long-chain structure helps increase the photoacid concentration in a certain zone and control the acid diffusion range to certain degree.

Description

technical field [0001] The invention relates to a photoacid generator and a preparation method thereof, in particular to a flexible long-chain multi-onium salt photoacid generator and a preparation method thereof. Background technique [0002] The three important parameters of photoresist include resolution, sensitivity, and line width roughness, which determine the process window of photoresist during chip manufacturing. As the performance of semiconductor chips continues to improve, the integration level of integrated circuits increases exponentially, and the graphics in integrated circuits continue to shrink. In order to make smaller-sized graphics, the performance indicators of the above three photoresists must be improved. According to the Rayleigh equation, the use of a short-wavelength light source in the photolithography process can improve the resolution of the photoresist. The light source wavelength of lithography process has developed from 365nm (I-line) to 248...

Claims

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Application Information

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IPC IPC(8): C07C319/12C07C321/10C07C303/22C07C309/12G03F7/004
Inventor 顾大公毛智彪许从应陈玲朱胜恺齐国强
Owner NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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