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Coumarin-based sulphonate photo-acid generator and preparation method therefor

A technology of photoacid generators and base sulfonate esters, which is applied in the field of photoacid generators, can solve problems affecting application, thermal stability and storage stability of oxime sulfonate compounds, and achieve fast acid production efficiency , easy to implement, high yield effect

Inactive Publication Date: 2016-05-25
SUZHOU RUIHONG ELECTRONIC CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the oxime sulfonate has a high acid production efficiency, there are certain problems in the thermal stability and storage stability of the oxime sulfonate compound, which affects its application in industrial production.

Method used

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  • Coumarin-based sulphonate photo-acid generator and preparation method therefor
  • Coumarin-based sulphonate photo-acid generator and preparation method therefor
  • Coumarin-based sulphonate photo-acid generator and preparation method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (1) Synthesis of 4-methyl-7-isooctyloxycoumarin

[0045]

[0046] 4-Methyl-7-hydroxycoumarin (1.76g, 10mmol), bromoisoctane (2.63mL, 15mmol) and anhydrous potassium carbonate (2.76g, 20mmol) were dissolved in 50mL of DMF, N 2 Under protection, stir at 60°C for 12h. After the reaction, the mixture was poured into 100 mL of deionized water, extracted three times with 30 mL of dichloromethane, and the organic phases were combined. After washing twice with 50 mL of water, it was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 12:1) to obtain a milky white liquid product, which became a white solid after cooling, with a yield of 91%.

[0047] 1 HNMR (400MHz, CDCl 3 )δ7.50(d, J=8.8Hz, 1H), 6.88(dd, J=8.8, 2.5Hz, 1H), 6.83(d, J=2.4Hz, 1H), 6.14(d, J=1.1Hz, lH), 3.96-3.87(m, 2H), 2.41(d, J=1.1Hz, 3H), 1.83-1.7...

Embodiment 2

[0061] (5) Synthesis of PAG-2

[0062]

[0063] Using a synthesis method similar to that of PAG-1, PAG-2 was synthesized from 4-trifluoromethylbenzenesulfonyl chloride. The product was a light yellow solid with a yield of 72%.

[0064] 1 HNMR (400MHz, CDCl 3 )δ8.07 (d, J=8.2Hz, 2H), 7.82 (d, J=8.2Hz, 2H), 7.34 (d, J=8.8Hz, 1H), 6.85 (dd, J=8.8, 2.2Hz, 1H), 6.80(d, J=2.1Hz, 1H), 6.29(s, 1H), 5.28(s, 2H), 3.91(d, J=5.6Hz, 2H), 1.92-1.68(m, 1H), 1.58-1.13(m, 9H), 1.10-0.70(m, 6H).

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Abstract

The invention discloses a coumarin-based sulphonate photo-acid generator (photo-generated acid) and a preparation method therefor. The photo-generated acid is obtained by an esterification reaction between a coumarin compound including hydroxyl, and sulfonyl chloride. The photo-generated acid can produce acidic materials under certain ultraviolet lights; and photoresist prepared from the photo-generated acid provided by the invention can be developed under ultraviolet lights, and has the characteristics of high activity and high precision.

Description

technical field [0001] The invention relates to the field of photoacid generators, in particular to a photoacid generator containing coumarin structural units and sulfonate groups and a preparation method thereof. Background technique [0002] Photoacid generators (photoacid generators) refer to a class of compounds that can generate acidic substances under certain light source radiation, and then serve as catalysts for further reactions. At present, photoacid generators have been widely concerned in the fields of photoresist, photosensitive resin, microelectronics industry and photodynamic therapy. Among them, photoresist is the most important application direction of photoacid generator. [0003] There have been many patent reports on the use of photosensitive oxime sulfonates as photoacid generators, such as CN103389621A and CN1246655A. Although oxime sulfonate has high acid production efficiency, there are certain problems in thermal stability and storage stability of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/004C07D311/16
CPCG03F7/004C07D311/16
Inventor 李治全朱桂刚刘敬成刘仁穆启道刘晓亚
Owner SUZHOU RUIHONG ELECTRONIC CHEM CO LTD
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