Photoinitiator containing nitro dioxime ester and preparation method and application thereof

一种硝基双肟、光引发剂的技术，应用在含硝基双肟酯类光引发剂及其制备领域，能够解决UV-LED光源发光光谱窄、光引发剂应用性能难以令人满意等问题

Active Publication Date: 2014-05-28
CHANGZHOU TRONLY NEW ELECTRONICS MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Due to the narrow emission spectrum of the UV-LED light source itself, the application performance of the existing photoinitiators under its excitation is unsatisfactory. agent becomes more important

Method used

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  • Photoinitiator containing nitro dioxime ester and preparation method and application thereof
  • Photoinitiator containing nitro dioxime ester and preparation method and application thereof
  • Photoinitiator containing nitro dioxime ester and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of 1-nitro-3-(1-oxime acetate)propyl-6-(1-oxime acetate-3-cyclohexyl)propyl-9-ethyl-carbazole

[0045]

[0046] Put 23.2g and 100g of 1-nitro-3-(1-ketoxime)propyl-6-(1-ketoxime-3-cyclohexyl)propyl-9-ethyl-carbazole into a 250mL four-neck flask Dichloromethane and 5.1g triethylamine were stirred at room temperature for 5min, then 11.3g of acetic anhydride was added dropwise, and the dropwise addition was completed in about 30min, continued stirring at room temperature for 2h, and then 5% NaHCO was added 3 Adjust the pH value of the aqueous solution to neutral, separate the organic layer with a separatory funnel, and then wash it twice with 200mL water, 50g of anhydrous MgSO 4 After drying, the solvent was evaporated by rotary evaporation to obtain a viscous liquid, which was recrystallized from methanol to obtain a white solid powder, which was filtered to obtain 24.7 g of the product with a yield of 90% and a purity of 99%.

[0047] The structure of the ...

Embodiment 2

[0050] 1,8-Dinitro-3-(1,2-diketo-2-oxime-O-benzoate-3-cyclobutyl)propyl-6-(1,2-diketo-2- Preparation of oxime-O-benzoate)propyl-9-ethyl-carbazole

[0051]

[0052] Put 1,8-dinitro-3-(1,2-diketone-2-oxime-3-cyclobutyl)propyl-6-(1,2-diketone-2- Oxime) propyl-9-ethyl-carbazole 24.8g, 100g dichloromethane and 5.1g triethylamine, stirred at room temperature for 5min, then added dropwise 14.3g of benzoyl chloride, about 30min after the dropwise addition was completed, continued to stir at room temperature for 2h , then add 5% NaHCO 3 Adjust the pH value of the aqueous solution to neutral, separate the organic layer with a separatory funnel, and then wash it twice with 200mL water, 50g of anhydrous MgSO 4 After drying, the solvent was evaporated by rotary evaporation to obtain a viscous liquid, which was recrystallized from methanol to obtain a white solid powder, which was filtered to obtain 20.9 g of the product with a yield of 87% and a purity of 99%.

[0053] The structure ...

Embodiment 3-15

[0056] With reference to the method of embodiment 1 or 2, by the corresponding compound containing nitrobisoximyl structure Compounds 3-15 shown in Examples 3-15 were prepared with acid halide compounds or acid anhydrides.

[0057] The structure of the target product and its 1 H-NMR data are listed in Table 1:

[0058] Table 1

[0059]

[0060]

[0061]

[0062] performance evaluation

[0063] By preparing an example photocurable composition, the application properties of the photoinitiator represented by the formula (I) of the present invention were evaluated, including storage stability, sensitivity, developability and pattern integrity.

[0064] 1. Preparation of photocurable composition

[0065] (1) Uncolored photocurable composition A

[0066] Acrylate Copolymer 100

[0067] (Benyl methacrylate / methacrylic acid / hydroxyethyl methacrylate (70 / 10 / 20 molar ratio) copolymer (Mw: 10,000))

[0068] Trimethylolpropane Triacrylate (TMPTA) 100

[0069] Photoinit...

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Abstract

The invention discloses a photoinitiator containing nitro dioxime ester. The structure of the photoinitiator is represented by a general formula I shown in the specification. The photoinitiator has excellent application properties on the aspects of storage stability, light sensitivity, developing performance, pattern integrity and the like, has good adaptability to single-wavelength UV-LED (Ultraviolet-Light Emitting Diode) light sources and shows light sensitization performance, which is obviously better than that of the existing photoinitiators, under the irradiation of UV-LED.

Description

technical field [0001] The invention belongs to the technical field of photoinitiators, in particular to a photoinitiator containing nitrobisxime esters and its preparation method and application. Background technique [0002] The use of compounds with carbazole, diphenyl sulfide and other groups connected with oxime ester structures as photoinitiators has been widely known in the art. Design and synthesis of new oxime esters with better application performance Initiators have also been a hot spot in the field of photocuring in recent years. For example, the publication numbers are CN1514845A, CN101508744A, CN101528694A and other Chinese patent documents disclose a variety of oxime ester photoinitiators, these products have good photosensitivity, storage stability, etc., to a certain extent meet and improve the development needs. [0003] However, it has been found in practice that, similar to traditional photoinitiators, these existing oxime ester photoinitiators have gre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48G03F7/004G03F7/027C07D209/88C07C323/47C07C319/20C07D333/76C07C251/66C07C249/12C07D307/91
CPCC07D333/76C07C323/47C07D209/88C07D307/91C08F2/50C07C2601/08C07C2601/14C07C251/66G03F7/031C08F220/06C08F220/14C08F220/20G03F7/004G03F7/027C08F265/06
Inventor 钱晓春钱彬胡春青王兵朱文斌
Owner CHANGZHOU TRONLY NEW ELECTRONICS MATERIALS
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