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Fluorene derivative, and photopolymerization initiator and photoresist composition containing same

A derivative, C3-C30 technology, applied in the fields of photopolymerization initiators and photoresist compositions containing the same, fluorene derivatives, and new fluorene derivatives, which can solve the problem of low sensitivity and low photopolymerization initiator usage or Exposure, mask contamination, yield reduction, etc., to achieve the effects of excellent reactivity, improved film retention rate, and high solubility

Active Publication Date: 2018-06-08
克美
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the case of forming a pattern using such a conventional photopolymerization initiator, the sensitivity in the exposure process is low, and it is necessary to increase the amount of the photopolymerization initiator used or the exposure amount, thereby contaminating the mask in the exposure process, and due to high temperature exposure Yield decreases due to by-products generated after the photopolymerization initiator decomposes, which becomes a stumbling block to increase productivity

Method used

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  • Fluorene derivative, and photopolymerization initiator and photoresist composition containing same
  • Fluorene derivative, and photopolymerization initiator and photoresist composition containing same
  • Fluorene derivative, and photopolymerization initiator and photoresist composition containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] (Example 1) Preparation of 1-(9,9-diallyl-9H-fluoren-2-yl)-1,2-propanedione-2-oxime-O-acetate (1)

[0109] Step 1. Preparation of 9,9-diallyl-9H-fluorene

[0110]Under a nitrogen atmosphere, dissolve 20.0g (120.32mmol) of fluorene, 27.0g (481.29mmol) of potassium hydroxide and 1.99g (12.03mmol) of potassium iodide in 140ml of anhydrous tetrahydrofuran, and after maintaining at 15°C, dissolve allyl bromide 30.57 g (252.67mmol) was diluted in 40ml of anhydrous tetrahydrofuran and added dropwise slowly. After the dropwise addition, the mixture was stirred at normal temperature (23° C.) for 1 hour. After slowly pouring into 300 ml of ice-distilled water to terminate the reaction, the product was extracted with 500 ml of dichloromethane. The organic layer was separated and washed with water twice. After drying the organic layer with anhydrous magnesium sulfate, the anhydrous magnesium sulfate was separated by filtration. The product obtained by concentrating the filtrate...

Embodiment 2

[0121] (Example 2) 1-(9-(3-methylenecyclohexyl)-9H-fluoren-2-yl)-1,2-propanedione-2-oxime-O-acetate (4)

[0122] Step 1. Preparation of 9-(3-cyclohexanonyl)-9H-fluorene

[0123] Under a nitrogen atmosphere, 10.0 g (60.16 mmol) of fluorene and 14.96 g (61.36 mmol) of 1,5-dibromopentan-3-one were dissolved in 350 ml of anhydrous tetrahydrofuran, and after maintaining at 5° C., 0.99 g of potassium iodide ( 6.01 mmol). 13.50 g (240.64 mmol) of potassium hydroxide was added bit by bit while preventing heat generation. After charging, the reactant was heated up to 15° C. and stirred for 1 hour, and then stirred at room temperature for 1 hour. After slowly pouring into 500 ml of ice-distilled water to terminate the reaction, the product was extracted with 300 ml of dichloromethane. The organic layer was separated and washed with water twice. After drying the organic layer with anhydrous magnesium sulfate, the anhydrous magnesium sulfate was separated by filtration. The product o...

Embodiment 3

[0131] (Example 3) 1-(9-(2-cyclopentenyl)-9H-fluoren-2-yl)-1,2-propanedione-2-oxime-O-acetate (6)

[0132] In step 1 of the above example 2, 1,4-dibromo-2-butene was used instead of 1,5-dibromopentan-3-one, except that, the same method was used to carry out the Step 1, prepare 9-(2-cyclopentenyl)-9H-fluorene, then use 9-(2-cyclopentenyl)-9H-fluorene instead of 9,9-di Allyl-9H-fluorene, except that, using the same method to carry out steps 2 to 4 in Example 1, to obtain light yellow solid 1-(9-(2-cyclopentenyl)-9H-fluorene -2-yl)-1,2-propanedione-2-oxime-O-acetate 3.18 g (66%).

[0133] 1 H-NMR (δppm: CDCl 3 ):2.20(3H,s),2.34(3H,s),2.62-2.76(4H,d),5.71-5.82(2H,d),7.35-7.48(3H,m),7.76-7.88(2H,d ),8.11-8.22(2H,d)

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Abstract

The present invention relates to a fluorene derivative, and a photopolymerization initiator and a photoresist composition containing the same. The fluorene derivative according to the present invention has an advantage of being capable of providing a photopolymerization initiator and a photoresist composition which can realize high sensitivity in a wide range absorption spectrum by containing a specific unsaturated substituent at the 9-position of fluorene.

Description

technical field [0001] The present invention relates to a fluorene derivative, a photopolymerization initiator containing the same, and a photoresist composition. More specifically, it relates to a novel fluorene derivative containing an unsaturated substituent at the 9-position, and a photopolymerization initiator containing the same and photoresist compositions. Background technique [0002] Since photopolymerization initiators can be selectively cured by irradiated light to form various patterns, they are used in photocurable inks, photosensitive printing plates, various photoresists, and the like. Various compounds such as acetophenone derivatives, benzophenone derivatives, biimidazole derivatives, acylphosphine oxide derivatives, triazine derivatives, and oxime derivatives are known as photopolymerization initiators having such characteristics. . Among them, oxime ester compounds containing a carbazole skeleton are disclosed in Patent Documents 1 to 3 (Japanese Patent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/567C07C13/72C07C219/22G03F7/004G03F7/00G02B5/20C07C219/08
CPCC07C13/567C07C13/72C07C219/08C07C219/22G02B5/20G03F7/00G03F7/004
Inventor 金星炫金相河许闰姬
Owner 克美
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