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Oxime ester sulfonate type photo-acid generator

A photoacid generator and oxime sulfonate technology, which is applied in the field of oxime sulfonate photoacid generators, can solve the problems that affect popularization and application and market expectations, low photosensitive activity, and can not meet the exposure requirements, etc., and achieve excellent application performance , High photosensitivity, high photosensitivity effect

Active Publication Date: 2013-11-13
CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing sulfonate products generally have the defect of low photosensitivity, which cannot meet the exposure requirements under i-line (365nm) and h-line (405nm), thus affecting the popularization and application of sulfonate photoacid generators. market expectation

Method used

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  • Oxime ester sulfonate type photo-acid generator
  • Oxime ester sulfonate type photo-acid generator
  • Oxime ester sulfonate type photo-acid generator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 1-[6-(2-thienyl)-9-ethylcarbazol-3-yl]-3-cyclopentyl-propane-1,2-dione-2-oxime methylsulfonate (i.e. Compound No.10)

[0029]

[0030] Step (1): Preparation of 3-(3-cyclopentylpropionyl)-6-(2-thienoyl)-9-ethylcarbazole

[0031]

[0032] Drop into 30g 9-ethylcarbazole, 21.6gAlCl in the 500ml four-necked flask 3 (Grinding), 150ml of dichloromethane, stirred, protected by argon, cooled in an ice bath, when the temperature dropped to 0°C, began to drop the mixture of 23.2g of 2-thiophenoyl chloride and 21g of dichloromethane, temperature controlled Below 10°C, add about 1.5h, continue to stir for 2h, then add 21.6g AlCl to the flask 3 (Grind finely), add dropwise a mixture of 27.2g cyclopentylpropionyl chloride and 20g dichloromethane, control the temperature below 10°C, drop it in about 1.5h, then raise the temperature to 15°C, continue stirring for 2h, and stop the reaction. Pour the reaction solution into dilute hydrochloric acid made of 400g ice ...

Embodiment 2

[0043] Preparation of 1-(6-o-methylbenzoyl-9-ethylcarbazol-3-yl)-3-cyclobutyl-propane-1-one oxime p-toluenesulfonate (Compound No. 2)

[0044]

[0045] Step (1): Preparation of 3-(3-cyclobutylpropionyl)-6-o-methylbenzoyl-9-ethylcarbazole

[0046]

[0047] Drop into 19.5g 9-ethylcarbazole, 13.5gAlCl in the 500ml four-necked flask 3 (Grind finely), 150ml of dichloromethane, stir, pass through argon protection, and cool in an ice bath. When the temperature drops to 0°C, start to drop a mixture of 15.5g of o-toluyl chloride and 15g of dichloromethane. The temperature was controlled below 10°C, the addition was completed in about 1.5 hours, and the stirring was continued for 2 hours, then 13.5g of AlCl was added to the flask 3 (Grind finely), add dropwise a mixture of 15g cyclobutylpropionyl chloride and 20g dichloromethane, keep the temperature below 10°C, drop it in about 1.5h, then raise the temperature to 15°C, continue to stir for 2h, stop the reaction. Pour the react...

Embodiment 3-4

[0056] Referring to the method shown in Example 2, the compounds of Examples 3 and 4 were prepared from the corresponding reagents. target compounds and their 1 H-NMR data are listed in Table 1.

[0057] Table 1

[0058]

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Abstract

The invention discloses an oxime ester sulfonate type photo-acid generator as shown in a formula (I). The oxime ester sulfonate type photo-acid generator is excellent in photosensitive property and capable of being well matched with I-ray and h-ray light sources, and has high luminous sensitivity and performances are obviously superior to those of conventional photo-acid generator products.

Description

technical field [0001] The invention belongs to the field of photoacid generators, in particular to a sulfonate oxime ester photoacid generator. Background technique [0002] Photoacid generators refer to compounds that can generate acidic substances when irradiated by ultraviolet light or electron beams. Among the existing photoacid generators, sulfonate photoacid generators are widely used and are an important part of chemically amplified photoresist. Specifically, under the irradiation of ultraviolet light of a certain wavelength and intensity, the photoactive sulfonate ester produces acidic substances, which then catalyzes the formulation system to cause a chemical reaction, and then undergoes processes such as developing, etching, and degumming to realize graphic Convert function. [0003] At present, there are some patent reports on sulfonate photoacid generators, such as CN1989455A, CN102712599A, CN1228851A and so on. However, the existing sulfonate products genera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/004C07D209/86C07D405/06C07D409/06C07C323/47C07C319/20
Inventor 钱晓春钱彬胡春青王兵李军
Owner CHANGZHOU TRONLY ADVANCED ELECTRONICS MATERIALS CO LTD
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