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Flavonol sulfonate photoacid generator and preparation method thereof

A technology of photoacid generator and flavonols, which is applied in the field of flavonol sulfonate photoacid generator and its preparation, can solve the problems of low acid generation efficiency, weak absorption, low sensitivity and the like, and achieves good curing effect Effect

Pending Publication Date: 2022-06-24
安庆北化大科技园有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its absorption above 405nm is weak, its sensitivity is low, and its acid production efficiency is low.

Method used

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  • Flavonol sulfonate photoacid generator and preparation method thereof
  • Flavonol sulfonate photoacid generator and preparation method thereof
  • Flavonol sulfonate photoacid generator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of Photoacid Generator 2-(4-(dimethylamino)phenyl)-4-oxo-4H-benzofuran-3-ylbenzenesulfonate

[0040] The synthesis process is shown in the following formula:

[0041]

[0042] In a 500ml round-bottomed flask, add 12g of sodium hydroxide, dissolve in 30ml of water, reduce the temperature to room temperature, then add 20ml of ethanol, weigh 4.86g of 2-hydroxyacetophenone and 5.33g of 4-(dimethylamino)benzaldehyde and mix , dissolve and dilute with 70ml ethanol, add half of the mixed solution dropwise to the round-bottomed flask, and add the remaining half after 30min. Incubate at 50°C until the reactants dissolve, react for 12h, then add 12ml H 2 O 2 Continue to react for 12h. After TLC detection, the raw material point disappeared. Adjust pH to 7 with dilute hydrochloric acid. The crude product was obtained by suction filtration. 2-(4-(dimethylamino)phenyl)-3-hydroxy-4H-chromium-4-one was obtained by recrystallization from ethanol / water (1:1 volume rat...

Embodiment 2

[0047] Synthesis of Photoacid Generator 2-(10-ethyl-10H-phenothiazin-3-yl)-4-oxo-4H-chromium-3-ylbenzenesulfonate

[0048] The synthesis process is shown in the following formula:

[0049]

[0050] 38.6 mL of DMF, 37.3 mL of phosphorus oxychloride, and 23.0 g of 10-ethyl-10H-phenothiazine were added to a 500-ml single-neck bottle, dissolved in 1,2-dichloroethane, and heated to 80°C. TLC detected the disappearance of the starting material, poured the reaction solution into 100 mL of ice water, adjusted the pH to neutrality with sodium hydroxide, extracted several times with dichloromethane, and concentrated to obtain 10-ethyl-10H-phenothiazine-3- formaldehyde.

[0051] Add 12g of sodium hydroxide to a 500ml round-bottomed flask, dissolve in 30ml of water, reduce the temperature to room temperature, then add 20ml of ethanol, weigh 4.86g of 2-hydroxyacetophenone and 9.13g of 10-ethyl-10H-phenothiazine- 3-formaldehyde was mixed, dissolved and diluted with 70 ml of ethanol, ha...

Embodiment 3

[0056] Synthesis of Photoacid Generator 2-(9-hexyl-9H-carbazol-3-yl)-4-oxo-4H-benzofuran-3-yl 4-(trifluoromethyl)benzenesulfonate

[0057] The synthesis process is shown in the following formula:

[0058]

[0059] 38.6 mL of DMF, 37.3 mL of phosphorus oxychloride, and 25.4 g of 9-hexyl-9H-carbazole were added to a 500-ml single-neck bottle, dissolved in 1,2-dichloroethane, and heated to 80°C. TLC detected the disappearance of the starting material, poured the reaction solution into 100 mL of ice water, adjusted the pH value to neutrality with sodium hydroxide, extracted with dichloromethane several times, and concentrated to obtain 9-hexyl-9H-carbazole-3-carbaldehyde.

[0060] Add 12g of sodium hydroxide to a 500ml round-bottomed flask, dissolve in 30ml of water, reduce the temperature to room temperature, then add 20ml of ethanol, weigh 4.86g of 2-hydroxyacetophenone and 9.99g of 9-hexyl-9H-carbazole-3- Formaldehyde was mixed, dissolved and diluted with 70 ml of ethanol, ...

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PUM

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Abstract

The invention relates to a sulfonate-based flavonol photo-acid generator, the structure of which is as shown in formula (I): wherein R1 is selected from one of triphenylamine, carbazole, phenothiazine, naphthalene, anthracene, pyrene and quinoline, and alkyl on carbazole or phenothiazine connected with N is selected from C1-C20 straight-chain alkyl or C1-C20 branched-chain alkyl; r2 is selected from one of methyl, trifluoromethyl, phenyl, 4-methyl phenyl and 4-trifluoromethyl phenyl. The acid generator realizes long-wave absorption based on a flavonol mother nucleus, has relatively strong absorption on 385nm, 395nm and 405nm UV LED light sources, and is high in light sensitivity. The structure contains a sulfonate group and is directly connected with a flavonol mother nucleus, the structure has a photosensitive cracking characteristic, superacid is generated through photolysis, the photolysis rate is further increased, and generated free radicals escape from a solvent cage to initiate free radical polymerization.

Description

technical field [0001] The invention relates to the field of photosensitive materials and photocuring, and more particularly, to a flavonol sulfonate photoacid generator and a preparation method thereof. Background technique [0002] Photoacid generator (PAG) is a kind of compound that can be decomposed to generate specific acid under the radiation of light, rays, plasma, etc. The acid produced can decompose or crosslink the acid-sensitive resin, so that the light Partial and non-illuminated parts dissolve with increased contrast. Because PAG system has good chemical amplification effect, high imaging sensitivity and recording accuracy, PAG is widely used in imaging systems such as cationic photocurable materials, thermal printing plates and chemically amplified resists. Photoacid generator is one of the key components in chemically amplified photoresist. Its structure and properties have a great influence on the image formed by the photoresist system. It should meet the re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07D417/04C07D405/04G03F7/004G03F7/027
CPCC07D311/30C07D417/04C07D405/04G03F7/0045G03F7/027
Inventor 王涛尤健
Owner 安庆北化大科技园有限公司
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