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Sulfur-containing unimolecule resin and photoresist composition thereof

A technology of composition and photoresist, which is applied in the field of materials, can solve the problem that the resolution of photoresist photolithography needs to be further improved

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

However, the resolution of the photoresist photolithography prepared by the above method still needs to be further improved.

Method used

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  • Sulfur-containing unimolecule resin and photoresist composition thereof
  • Sulfur-containing unimolecule resin and photoresist composition thereof
  • Sulfur-containing unimolecule resin and photoresist composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Preparation of bis-(3,5-dibromo-4-hydroxyphenyl)-thione, the synthetic route is as follows:

[0079]

[0080] 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. In a cold water bath at 5°C, add carbon disulfide solvent (100 mL) 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

[0082] Preparation of bis-(3,5-dibromo-4-methoxyphenyl)-thione, the synthetic route is as follows:

[0083]

[0084] 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, without 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%. 1 H NMR (400MHz, DMSO-d 6 ) δ (ppm) 3.88, (s, 6H), 7.81 (s, 4H).

Embodiment 3

[0086] To prepare 3,5-bis(3,4-dimethoxyphenyl)-4-methoxyphenyl-thione, the synthetic route is as follows:

[0087]

[0088] Concrete steps: under the protection of high-purity nitrogen, add bis-(3,5-dibromo-4-methoxyphenyl)-thione (5.8g, 10mmol, 1.0eq) in a 250mL Schleck reaction flask, 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, -OCH3 ),3.89(s,12H,-...

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Abstract

The invention discloses a compound as shown in a formula (I). In the formula, R0 and Ra1-Ra12 are the same or different and independently represent H, hydroxyl or ORb, Rb is an acid-sensitive group, and a condition is that at least one of the groups R0 and Ra1-Ra12 is not H. The compound as shown in the formula (I) has a determined molecular structure, is small and single in molecular size, can beused as a photoresist material and can be prepared into positive photoresist or negative photoresist according to the photoetching requirement in a use process, and the photoetching material can meetthe requirement of high-resolution photoetching. The compound as shown in the formula (I) is connected by taking a sulfur atom as a central atom, so that the refractive index of the photoetching material can be effectively improved and the photoetching resolution is improved; and meanwhile, the compound has better solubility and film-forming property.

Description

technical field [0001] The invention belongs to the technical field of materials, and in particular relates to a class of sulfur-containing monomolecular resin and its photoresist composition, photoresist coating and application thereof. Background technique [0002] Photoresist, also known as photoresist, is a kind of etching-resistant film material whose solubility changes after being irradiated by energy such as beam, electron beam, ion beam or x-ray. Photoresists are widely used in the microfabrication of integrated circuits and semiconductor discrete devices. 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...

Claims

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Application Information

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IPC IPC(8): C07C323/20G03F7/004G03F7/039
CPCC07C323/20G03F7/004G03F7/039C07C2602/42C07C2603/74
Inventor 李嫕张卫杰陈金平于天君曾毅
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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