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Ketoxime ester compound and use thereof

A technology of ester compounds and compounds, which is applied in the field of ketoxime ester compounds and photopolymerizable compositions, can solve the problems of low sensitivity and poor productivity, and achieve the effect of high transmittance, high sensitivity and transmittance

Active Publication Date: 2014-08-06
MITSUBISHI RAYON CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, compared with photopolymerizable negative photosensitive compositions, there are also problems such as low sensitivity and poor productivity.

Method used

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  • Ketoxime ester compound and use thereof
  • Ketoxime ester compound and use thereof
  • Ketoxime ester compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0513] [Example 1] (manufacture of ketoxime ester compound I-1)

[0514]

[0515] Ethylcarbazole (5g, 25.61mmol) and o-naphthoyl chloride (5.13g, 26.89mmol) were dissolved in 30ml of dichloromethane, stirred after cooling to 2°C in an ice-water bath, and aluminum chloride (3.41 g, 25.61 mmol). Stirring was further performed at room temperature for 3 hours. The reaction solution was poured into 200 ml of ice water, 200 ml of dichloromethane was added, and the organic layer was separated. The recovered organic layer was dried over magnesium sulfate and evaporated to give a white solid (10 g). The reaction formula is shown below.

[0516] [chemical formula 25]

[0517]

[0518]

[0519] Dissolve monoketone (7.05g, 22.34mmol) and 3-methylthiopropionyl chloride (3.77g, 21.06mmol) in 100ml of dichloromethane, cool to 2°C in an ice-water bath, stir, and add chloride Aluminum (6.30 g, 40.21 mmol). Stirring was further performed at room temperature for 3.5 h...

Embodiment 2

[0536] [Example 2] (manufacture of ketoxime ester compound 1-2)

[0537]

[0538] According to the same method as in Example 1, obtain 12.4 g of white solid. The reaction formula is shown below.

[0539] [chemical formula 30]

[0540]

[0541]

[0542] According to the same method as in Example 1, 2.0 g of diketone (3.82 g, 8.61 mmol), isoamyl nitrite (1.36 g, 11.62 mmol), and trimethylsilyl chloride (3.12 g, 27.72 mmol) were obtained to obtain 2.0 g of diketone yellow crystals. The reaction formula is shown below.

[0543] [chemical formula 31]

[0544]

[0545]

[0546] According to the same method as in Example 1, 1.6g of the following ketoxime ester compounds were obtained from ketoxime (5.0g, 10.32mmol), acetyl chloride (1.62g, 20.64mmol), triethylamine (2.09g, 20.64mmol) White crystals of I-2.

[0547] [chemical formula 32]

[0548]

[0549] The NMR chemical shift values ​​of this compound are shown below.

[0550] ...

Embodiment 3

[0555] [Example 3] (manufacture of ketoxime ester compound I-8)

[0556] Except that the glutaric acid monoethyl chloride used in the manufacture of the diketone body in the above-mentioned Example 2 was changed to glutaric acid monomethyl chloride, the following ketoxime ester compound I was produced according to the same method as in Example 2- 8. The NMR chemical shift values ​​of the obtained compound are shown below.

[0557] 1 H-NMRδ[ppm]

[0558] 1.49(t, 3H), 2.29(s, 3H), 2.36(s, 3H), 2.73(t, 2H), 3.14(t, 2H), 3.60(s, 3H), 4.43(q, 2H), 7.3 ~7.5(m, 6H), 8.06(dd, 1H), 8.29(dd, 1H), 8.59(d, 1H), 8.83(dd, 1H)

[0559] [chemical formula 34]

[0560]

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Abstract

The present invention provides a ketoxime ester compound that can be used as a novel and highly sensitive photopolymerization initiator, and a compound that is useful in interlayer insulating film applications and color filter applications with high sensitivity and high transmittance. Photopolymerizable composition. Therefore, the present invention relates to a ketoxime ester compound having a specific structure and a photopolymerizable composition containing the ketoxime ester compound.

Description

technical field [0001] The present invention relates to a ketoxime ester compound useful as a photopolymerization initiator, a photopolymerization initiator containing the compound, and a photopolymerizable composition containing the photopolymerization initiator. More specifically, it relates to a photopolymerizable composition suitable for forming, for example, liquid crystal display elements, plasma displays, printed wiring boards, large scale integrated circuits, thin transistors, semiconductor packages, color filters , Insulation coating layers, solder resist films, cover films, etc. of various electronic components in organic electroluminescent elements, etc. [0002] In addition, since the ketoxime ester compound of the present invention can be made into a highly sensitive photopolymerization initiator, it can be used in optical color filters used in color televisions, liquid crystal display elements, solid-state imaging elements, cameras, etc. Colorant-containing phot...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/63C07D209/86C07D295/14G02B5/20G03F7/031
CPCG03F7/0045C07C323/47C07D209/86G03F7/0007C07C323/63G03F7/031
Inventor 龟山泰弘高桥裕子水上润二
Owner MITSUBISHI RAYON CO LTD
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