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Cyclopentadiketoxime ester and applications thereof

A cycloalkyl and compound technology, applied in the field of oxime ester compounds, can solve the problems of no improvement in photosensitivity, increase in molecular weight, and difficulty in manufacturing

Active Publication Date: 2014-08-20
INSIGHT HIGH TECH (BEIJING) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, there are many other patents of oxime ester photoinitiators, such as: WO2006018973, WO2007071497, CN1805955B, CN1922142B, CN1928715A, CN101508744B, CN102020727, but they are all side chains at the 3, 6, and 9 positions of carbazole Various modifications are carried out on it, and some molecular weights increase without any improvement in photosensitivity, and are often difficult to manufacture. For example, the substituted carbazoloheterocyclic diketoxime ester described in the CN102046667B patent is very difficult to manufacture

Method used

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  • Cyclopentadiketoxime ester and applications thereof
  • Cyclopentadiketoxime ester and applications thereof
  • Cyclopentadiketoxime ester and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138] Synthesis of 5-methylthioindan-1,2-dione-2-oxime-O-acetate

[0139]

[0140] 1 a , Synthesis of 5-methylthioindan-1-one—etherification method A

[0141]

[0142] Weigh 3.33g (0.02mol) of 5-chloro-1-indanone in a 50ml three-necked flask, add 15ml of N,N-dimethylacetamide, 4.2g (0.03mol) of 50% sodium methyl mercaptide solution, nitrogen Protected, stirred at 20-25°C for 5h, added the reaction solution into 100ml of water, extracted twice with 25ml of 1,2-dichloroethane, combined the 1,2-dichloroethane solution, washed twice with 10ml of water, concentrated the organic solution To dryness, the residue was recrystallized with ethanol, and after drying, 2.5 g of off-white crystals was obtained, with a yield of 70.2%; the analytical purity was 98.02%, and the melting range was 105-106°C.

[0143] 1b, Synthesis of 5-methylthioindan-1,2-dione-2-oxime—oximation method A

[0144]

[0145] Take 1.8g (0.01mol) of the etherification product obtained in 1a, dissolve it i...

Embodiment 2

[0149] Synthesis of 5-(2-Acetoxyethylthio)indan-1,2-dione-2-oxime-O-acetate

[0150]

[0151] 2a, according to the 1a etherification method A of Example 1, with? 2-Mercapto? Ethanol and sodium hydroxide replaced 50% sodium methyl mercaptide solution, reacted with 5-fluoro-1-indanone to synthesize 5-(2-hydroxyethylthio)indan-1-one, light yellow crystal, yield 91.1 %.

[0152]

[0153] 2b, according to the 1b oximation method of Example 1, the product obtained in 2a is? The raw material was oximated and crystallized by methanol to obtain 5-(2-hydroxyethylthio)indan-1,2-dione-2-oxime as a light yellow solid product with a yield of 83.2%.

[0154]

[0155] 2c, according to the 1c esterification method of Example 1, increase the reaction temperature to 45-50 ° C, and obtain the light yellow powdery diacetate product 5-(2-acetoxyethylthio)indan-1 after purification, 2-diketo-2-oxime-O-acetate, purity 99.23%, yield 85.2%, melting range and 1 H-NMR (CDCl 3 ), δ (ppm) va...

Embodiment 3

[0157] Synthesis of 5-(4-isopropylphenylthio)indan-1,2-dione-2-oxime-O-acetate

[0158]

[0159] 3a, Synthesis of 5-(4-isopropylphenylthio)indan-1-one—etherification method B

[0160]

[0161] Weigh 3.33g (0.02mol) of 5-chloro-1-indanone in a 50ml three-necked flask, add 30ml of N,N-dimethylformamide (DMF), 4.2g (0.027mol) of 4-isopropylthiophenol , 3.0g anhydrous sodium carbonate, under nitrogen protection, stirred at 40-45°C for 6h; recovered DMF under reduced pressure, added the residue to 100ml water, extracted twice with 25ml 1,2-dichloroethane, combined 1,2-dichloroethane The ethyl chloride solution was washed twice with 10ml of water, and a 3cm-thick silica gel was spread in a Buchner funnel, and the organic phase was filtered with suction, the filtrate was concentrated to dryness, the residue was recrystallized with methanol, and 5.11g of light yellow crystals were obtained after drying. The yield is 90.6%; the analytical purity is 98.2%, and the melting range i...

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Abstract

The invention relates to compounds represented by the formula I, IIa, IIb, III, and IV and manufacturing methods thereof; wherein Ar1 stands for substituted o-arylidene or substituted o-heteroarylidene; Ar2 represents dual o-arylidene or dual o-heteroacylidene connected in various forms; Y1 represents O, S, NR20, BR20, CR15, R16, SiR15R16, S=O, or C=O; Z1 represents a straight bond, a C1-C10

Description

technical field [0001] The present invention relates to an oxime ester compound, which is characterized in that it is an esterified derivative of arylene pentacyclopentadione oxime, and the esterified oxime group is at the 2-position, which has the use as a photoinitiator in a photocurable composition. Background technique [0002] Oxime ester compounds have been discovered as photoinitiators very early. Both US3558309 and US4255513 patents have disclosed oxime ester compounds as photoinitiators. However, the oxime esters of some structures have poor thermal stability or low sensitivity, so it is difficult to Thermal stability, sensitivity and other properties meet the requirements of the modern electronics industry. CN1514845A discloses a series of oxime ester compounds, and two varieties OXE01 and OXE02 are on the market. Products with similar properties include oxime esters 305 and 304 disclosed in CN101565472B and CN101508744B. [0003] [0004] In addition, there ar...

Claims

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Application Information

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IPC IPC(8): C07C319/20C07C323/36C07C323/37C07D319/08C07D333/78C07D209/94C07F7/10C07D493/04G02B5/23C09D11/101G03F7/027C09D4/02C09D7/12C09J4/02C09J11/06
CPCC07D209/86C07D295/135C07D307/83C07D307/937C07D333/66C07D333/78C07D493/04C08F2/50C09B55/009C09B57/00G02B1/04G02B5/201G03F7/0007G03F7/029G03F7/031C07C251/20C07D307/88
Inventor 赵文超麻忠利王辰龙胡伟静姚丽秀王永林
Owner INSIGHT HIGH TECH (BEIJING) CO LTD
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