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Photosensitizer and preparation method thereof

A photosensitizer and carbon number technology, applied in the preparation of sulfonates, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of weak performance of photosensitizers, inability to disperse uniformly, etc., and achieve simple steps and good appearance. and line width roughness, the effect of uniform distribution

Pending Publication Date: 2022-04-12
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 embodiments of the present invention provide a photosensitizer and a preparation method thereof, aiming to solve the problem that the photosensitizers in the existing technology are basically diphenyliodonium salts and have no other modifying functional groups, which cannot be used in the photoresist system. Uniform dispersion, the problem that the existing photosensitizer has weak performance in the photoresist system

Method used

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  • Photosensitizer and preparation method thereof
  • Photosensitizer and preparation method thereof
  • Photosensitizer and preparation method thereof

Examples

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Embodiment 1

[0040] Provided in this example is (4-(methacryloyloxy)phenyl)(p-tolyl)iodonium as a photosensitizer and its preparation method. In the preparation process of this implementation, 34.66g of 4-hydroxyl, 4-methyldiphenyliodonium chloride salt was added to the reaction flask, 150ml of dichloromethane was added, dissolved, and 11.5g of triethylamine solution was added dropwise. The reaction flask was stirred at room temperature for 0.5 h under nitrogen protection, and then cooled to -5 °C. In another reaction bottle, pre-mix 11.7 g of methacryloyl chloride and dissolve in 30 ml of dichloromethane, slowly control the dropping speed, add the mixed solution of methacryloyl chloride, and control the temperature at -5°C. After the dropwise addition of the methacryloyl chloride mixture was completed, the mixture was stirred at -5°C for 1 h. After stirring at -5°C for 1h, the temperature was naturally raised to 25°C, and then stirred for 2h. The mixture was filtered, the filter cake wa...

Embodiment 2

[0045] In the present embodiment, the preparation process of the photosensitizer is as follows: add 28.9g 4-hydroxyl, 4-tert-butyldiphenyliodonium chloride salt in the reaction flask, add 150ml of dichloromethane, dissolve it, add dropwise 11.5 g triethylamine solution. Stir at room temperature for 0.5 h under nitrogen protection, then cool to -5°C. In another reaction bottle, 11.7 g of methacryloyl chloride was pre-mixed and dissolved in 30 ml of methylene chloride. Slowly control the dropping rate, add the methacryloyl chloride mixture, and control the temperature at -5°C. After the dropwise addition of the methacryloyl chloride mixture was completed, the mixture was stirred at -5°C for 1 h. Stir at -5 °C for 1 h, then naturally warm up to 25 °C, and stir for 2 h. After filtering, the filter cake was washed with 30 ml of dichloromethane, and the filtrate was washed twice with 10 ml of pure water. Concentrate the filtrate and control the temperature at 35°C. 39.1 g of (4...

Embodiment 3

[0049]In this example, the preparation process of the photosensitizer is as follows: add 42.9g (4-((methacryloyloxy)methyl)phenyl)(p-tolyl)iodonium into the flask, add 200g purified Mixture of water and 100ml methanol, dissolve clear. Add 30 g of methanol aqueous solution of 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonylimide salt into another reaction bottle, and it is in a clear state. As the addition proceeded, a white solid precipitated out. Stir overnight at room temperature. Desolvation, add 250ml of dichloromethane, stir, wash with 100ml of purified water*3 times, and desolventization to obtain 63.8g of the target product (4-((methacryloxy)methyl)phenyl)(p-tolyl) The yield of iodonium 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonylimide salt was 93.2%.

[0050] Its reaction formula is:

[0051]

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Abstract

The invention is suitable for the technical field of photosensitizers, and provides a photosensitizer and a preparation method thereof. The structural general formula of the photosensitizer is shown in the specification, wherein R1 is one or more of substituent groups containing sulfur / oxygen / nitrogen heteroatoms of aromatic hydrocarbon with 1-10 hydrogen and carbon atoms; r2 is one or more of hydrogen, methyl, propyl, isopropyl, n-butyl, tertiary butyl, methoxyl, ethyoxyl, propoxy, isopropoxy, isobutoxy or fluorine, bromine and iodine; r3 is one or more of hydrogen, aromatic hydrocarbon of alkane with the carbon atom number of 1-10 or substituent groups containing sulfur / oxygen / nitrogen heteroatoms; r4 is one or more of hydrogen, aromatic hydrocarbon of alkane with the carbon atom number of 1-10 or substituent groups containing sulfur / oxygen / nitrogen heteroatoms. According to the photosensitizer and the preparation method thereof, the diffusion range can be effectively controlled, the photoresist has better morphology and line width roughness, defects are reduced, meanwhile, the preparation method provided by the invention is simple in step, and various photosensitizers can be prepared.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a photosensitizer and a preparation method thereof. Background technique [0002] Photoresist, also known as photoresist, refers to a resist-etched film material whose solubility changes through irradiation or radiation of ultraviolet light, electron beams, ion beams, X-rays, etc. Photoresist is one of the key materials for micrographic processing in microelectronic processing technology. It is a photosensitive film that transfers images to substrates. The mixed liquid is often used as an anti-corrosion coating material in the photolithography process. The main components of photoresist are polymer resin, photosensitizer and corresponding additives. Photosensitizer is an important component in the photoresist system. It generates acid (H+) under light. During the post-exposure baking process, these acids will act as catalysts to detach unstable gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07D285/16C07C309/06C07C317/04G03F7/004C07C315/04C07C303/32
Inventor 夏力顾大公马潇陈鹏许从应毛智彪
Owner NINGBO NATA OPTO ELECTRONICS MATERIAL CO LTD
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