Sulfonium salt-based monomolecular resin acid producing agent and photoresist composition thereof

A technology of compound and alkyl, applied in the field of single-molecule resin acid generator and its photoresist composition

Active Publication Date: 2020-11-24
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some single-component photoresists have been disclosed in the prior art, but the film-forming properties, solubility, glass transition temperature and etch resistance of these materials need to be further improved

Method used

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  • Sulfonium salt-based monomolecular resin acid producing agent and photoresist composition thereof
  • Sulfonium salt-based monomolecular resin acid producing agent and photoresist composition thereof
  • Sulfonium salt-based monomolecular resin acid producing agent and photoresist composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Preparation of bis-(3,5-dibromo-4-hydroxyphenyl)-thione, the synthetic route is as follows:

[0097]

[0098] Specific steps: Add 2,6-dibromophenol (25.2g, 100.0mmol, 1.0eq) and thionyl chloride (5.95g, 50mmol, 0.5eq.) into a 250ml three-neck flask equipped with a condenser tube, Connect an inverted funnel with a catheter to the 30% NaOH aqueous solution to absorb the HCl produced by the reaction. Under the cold water bath of 5 ℃, add carbon disulfide solvent (100ml) and AlCl to the reaction system 3 (1.3g, 10mmol, 0.1eq), continue to stir and react in the cold water bath for 1 hour, then remove the cold water bath, return to room temperature and react for about 3 hours, and finally the reaction system is heated to 60°C in the oil bath for 4 hours, and the reaction solution After cooling to room temperature, a large amount of white solid was precipitated, filtered, and the filter cake was recrystallized with ethanol to obtain 23.3 g of the product with a yield of 85...

Embodiment 2

[0100] Preparation of bis-(3,5-dibromo-4-methoxyphenyl)-thione, the synthetic route is as follows:

[0101]

[0102] Specific steps: Add bis-(3,5-dibromo-4-hydroxyphenyl)-thione (11.0g, 20.0mmol, 1.0eq) into a 250ml three-necked flask equipped with a condenser, 120ml of dry acetone, no Potassium carbonate water (5.5g, 40mmol, 2.0eq), methyl iodide (8.5g, 60mmol, 3.0eq.), reflux reaction under nitrogen protection for 24 hours, the reaction solution was cooled to room temperature, the solvent was removed under reduced pressure, and dichloromethane extracted with water, combined the organic layers, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and recrystallized in ethyl acetate to obtain 10.2 g of a white solid with a yield of 88%.

[0103] 1 H NMR (400MHz, DMSO-d 6 ) δ (ppm) 3.88 (s, 6H), 7.81 (s, 4H).

Embodiment 3

[0105] To prepare 3,5-bis(3,4-dimethoxyphenyl)-4-methoxyphenyl-thione, the synthetic route is as follows:

[0106]

[0107] Concrete steps: under the protection of high-purity nitrogen, add two-(3,5-dibromo-4-methoxyphenyl)-thione (5.8g, 10mmol, 1.0eq) in the Schleck reaction flask of 250ml, Pd ( PPh 3 ) 4 (578mg, 0.5mmol, 0.05eq), 3,4-dimethoxyphenylboronic acid (9.1g, 50.0mmol, 5.0eq), the system was under a nitrogen atmosphere, and finally added redistilled dioxane 100ml, water 20ml , the reaction solution was heated to reflux for 24h, cooled to room temperature, and extracted with dichloromethane / water, the organic layers were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and recrystallized in ethyl acetate to obtain 6.7g of a white solid, the yield 83%. 1 H NMR (400MHz, CDCl 3 )δ (ppm) 7.61 (s, 4H, benzene ring), 7.10-7.07 (m, 8H, benzene ring), 6.94-6.92 (d, 4H, benzene ring), 3.92 (s, 12H, -OCH 3 ),3.89...

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Abstract

The invention belongs to the technical field of materials, and particularly relates to a sulfonium salt-based monomolecular resin acid producing agent and a photoresist composition thereof. The invention mainly provides a compound as shown by formula I and a photoresist composition thereof. The compound of the invention has dual functions of acid producing and acid sensing, and not only can be used as an acid producing agent of a photoresist, but also can be used as a main material of the photoresist. The acid producing agent is conducive to realizing regulation on acid diffusion and effectivereduction of edge roughness.

Description

technical field [0001] The invention belongs to the technical field of materials, and in particular relates to a sulfonium salt-based monomolecular resin acid generator and a photoresist composition thereof. Background technique [0002] Photoresist, also known as photoresist, is a kind of etch-resistant thin film material whose solubility changes after energy radiation such as beam, electron beam, ion beam or x-ray, and is widely used in integrated circuits and semiconductor discrete devices. microfabrication. By coating the photoresist on the surface of a semiconductor, conductor or insulator, the part left after exposure and development will protect the bottom layer, and then use an etchant to etch to transfer the required fine pattern from the mask to the substrate. Therefore, photoresist is a key material in device microfabrication technology. With the rapid development of the semiconductor industry, the resolution required by photolithography technology is getting hi...

Claims

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Application Information

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IPC IPC(8): C07C381/12G03F7/004
CPCC07C381/12G03F7/004
Inventor 陈金平李嫕张卫杰于天君曾毅
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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