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Carbazole oxime ester compound and its synthesis method and application

A technology of ester compounds and carbazole oxime, which is applied in the preparation method and in the field of photoinitiators, carbazole oxime ester compounds, and photoinitiators, can solve the problem of poor sensitivity, thermal stability and solubility of photoinitiators, issues such as low mobility

Active Publication Date: 2021-02-09
JIANGSU HECHENG ADVANCED MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Purpose of the invention: In order to solve the problems of relatively poor sensitivity, thermal stability and solubility of the existing carbazole oxime ester photoinitiators, the present invention provides a solution with good solubility, good thermal stability, high reactivity and low production cost. New carbazole oxime ester compound with low cost, low price, basically no odor, low migration, and high safety (low toxicity)

Method used

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  • Carbazole oxime ester compound and its synthesis method and application
  • Carbazole oxime ester compound and its synthesis method and application
  • Carbazole oxime ester compound and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Preparation of o-methylbenzoyl chloride (Ⅰ-1-1-1)

[0085]

[0086] Add 100ml of dichloromethane, 20g of o-toluic acid and 2 drops of DMF to a three-necked flask, connect a reflux condenser, a constant pressure dropping funnel, a drying tube and a lye tail gas absorption device, heat to reflux at 55°C, and slowly add Add 18g of thionyl chloride dropwise for about 0.5h, reflux for 1.5h, concentrate under reduced pressure, add 100ml of fresh dichloromethane and concentrate under reduced pressure again to obtain a light yellow solution, which is compound Ⅰ-1-1-1.

[0087] Preparation of 1-(6-(2-methylbenzoyl)-9-ethylcarbazole)ethanone (compound Ⅰ-1-1-2)

[0088]

[0089] In a three-necked flask, add 27g of 9-ethylcarbazole and 100ml of dichloromethane, blow nitrogen, and add 20g of anhydrous A1C1 3 , add a drying tube, a reflux condenser and a tail gas absorption device, cool down to -5°C in an ice-salt water bath, and slowly drop a mixture of 22g of o-toluyl chlori...

Embodiment 2

[0100] Preparation of 3-benzoyl-2,4,6-trimethylbenzoyl chloride (Ⅰ-1-1-4)

[0101]

[0102] Add 100ml of ethyl acetate, 20g of 3-benzoyl-2,4,6-trimethylbenzoic acid and 2 drops of DMF to the three-necked flask, and connect the reflux condenser, constant pressure dropping funnel, drying tube and lye tail gas Absorption device, heated to reflux, slowly add 10g of thionyl chloride dropwise, about 20min to complete the dropwise addition, reflux for 2h, concentrate under reduced pressure, add 100ml of fresh dichloromethane and concentrate under reduced pressure again to obtain brown yellow oily liquid, which is compound Ⅰ -1-1-4.

[0103] 1-(6-(3'-benzoyl-2',4',6'-trimethylbenzoyl)-9-ethylcarbazole)ethanone (compound Ⅰ-2-1-1) preparation

[0104]

[0105] In a three-necked flask, add 27g of 9-ethylcarbazole and 100ml of dichloromethane, blow nitrogen, and add 20g of anhydrous A1C1 3 , add a drying tube, a reflux condenser and a tail gas absorption device, cool down to -5°C...

Embodiment 3

[0113] Preparation of 3-benzoyl-2,4,6-trimethylbenzoyl chloride (Ⅰ-1-1-4)

[0114]

[0115] Add 100ml of ethyl acetate, 20g of 3-benzoyl-2,4,6-trimethylbenzoic acid and 2 drops of DMF to the three-necked flask, and connect the reflux condenser, constant pressure dropping funnel, drying tube and lye tail gas Absorption device, heated to reflux, slowly add 10g of thionyl chloride dropwise, about 20min to complete the dropwise addition, reflux for 2h, concentrate under reduced pressure, add 100ml of fresh dichloromethane and concentrate under reduced pressure again to obtain brown yellow oily liquid, which is compound Ⅰ -1-1-4.

[0116] 1-(6-(3'-benzoyl-2',4',6'-trimethylbenzoyl)-9-ethylcarbazole)ethanone (compound Ⅰ-2-1-1) preparation

[0117]

[0118] In a three-necked flask, add 27g of 9-ethylcarbazole and 100ml of dichloromethane, blow nitrogen, and add 20g of anhydrous A1C1 3 , add a drying tube, a reflux condenser and a tail gas absorption device, cool down to -5°C i...

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Abstract

The invention discloses a carbazole oxime ester compound represented by general formula I. The carbazole oxime ester compound having the structure of general formula I has the characteristics of good solubility, high thermal stability, high photosensitive activity and low toxicity. Moreover, the photoinitiator has excellent application performance and has particularly high photosensitivity, especially under exposure light sources such as LEDs and LDIs, it has shown very high photosensitivity activity, which significantly improves the performance of photosensitive compositions such as preparing color filters, etc. The production efficiency in the application field is obviously better than the existing products. .

Description

technical field [0001] The invention relates to the technical field of photoinitiators, in particular to a carbazole oxime ester compound, a preparation method and its application in the technical field of photoinitiators. Background technique [0002] Photocuring is the process of irradiating chemically active liquid materials with ultraviolet light, triggering their rapid polymerization and crosslinking, and making them solidify instantly. This technology has a wide range of applications in modern microelectronics technology, such as photocurable inks, packaging of liquid crystal panels, photosensitive printing plates, optical filters and photoresists, etc. [0003] The photoinitiator is the most important factor affecting the photosensitivity of the photocurable composition (ie photosensitive composition). At this stage, there have been many studies and reports on photoinitiators, but these photoinitiators generally have low sensitivity to cleanliness, and there are grea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07D409/06C08F2/48
CPCC07D209/86C07D409/06C08F2/48
Inventor 胡海军吴进谭玉东黎水林黄达
Owner JIANGSU HECHENG ADVANCED MATERIALS