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Olefin monomer containing 8-hydroxyquinoline metal complex and its production method and use

A technology of metal complexes and hydroxyquinoline, applied in compounds containing elements of group 3/13 of the periodic table, compounds of group 2/12 elements of the periodic table, organic chemistry, etc., can solve compatibility problems that are difficult to solve , poor product solubility, low luminous efficiency, etc., to achieve the effects of high content of 8-hydroxyquinoline metal complexes, excellent processing performance, photoelectric performance, and high luminous efficiency

Inactive Publication Date: 2007-05-16
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In practical application, both methods have obvious shortcomings: Usually, the electroluminescent device is prepared by the former application method by evaporation of small molecules to form a film. Due to the high temperature during sublimation, small molecules are easy to produce oligomers or isomers. , and the crystallization of small molecules when the device is working will greatly affect the life of the device, and this method is not easy to realize the preparation of large-area devices. Compared with solution spin coating or spray printing, it is a high-cost preparation process; the latter application method Although these problems have been solved, the compatibility between the 8-hydroxyquinoline metal complex and the polymer matrix is ​​difficult to solve, which makes the material phase separation in a short time and shortens the working life of the device.
At present, there are few researches on the synthesized polymerized 8-hydroxyquinoline metal complexes, and most of the polymerized 8-hydroxyquinoline metal complexes reported in the literature have complex preparation methods, low yields, and poor product solubility. , low luminous efficiency and other disadvantages

Method used

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  • Olefin monomer containing 8-hydroxyquinoline metal complex and its production method and use
  • Olefin monomer containing 8-hydroxyquinoline metal complex and its production method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 100 parts of allyl alcohol, add -CH 2 5 parts of 8-hydroxyquinoline with Cl substituent, under the catalysis of 1.0 parts of sodium hydroxide, 1 part of p-hydroxyphenol as a polymerization inhibitor, the temperature is controlled at 50 ° C and stirred, and the reaction is controlled for 24 hours. After the reaction is completed, add 500 parts of water, drop Add an appropriate amount of dilute ammonia water with a weight concentration of 1% to neutrality to obtain a white precipitate, and recrystallize petroleum ether 3 times to obtain an alkene monomer containing 8-hydroxyquinoline ligand; take 1 part of aluminum isopropoxide and dissolve it in 20 1 part of tetrahydrofuran, add 4 parts of vinylic monomers containing 8-hydroxyquinoline ligand, stir and react at room temperature for 8 days, let stand for 1 day, filter to obtain filtrate, add water to precipitate, filter to obtain solid, petroleum ether recrystallization 3 times, A vinylic monomer containing an aluminum co...

Embodiment 2

[0032] 100 parts of p-vinylbenzyl chloride, add -CH 2 10 parts of 8-hydroxyquinoline with OH substituent, under the catalysis of 0.5 parts of sodium acetate, 2 parts of benzoquinone as a polymerization inhibitor, the temperature is controlled at 100 ° C and stirred, and the reaction is controlled for 18 hours. After the reaction is completed, add 200 parts of water and drop an appropriate amount Dilute ammonia water with a weight concentration of 3% to neutrality, a white precipitate is obtained, petroleum ether is recrystallized 3 times, and an alkene monomer containing 8-hydroxyquinoline ligand is obtained; 1 part of triethylaluminum is dissolved in 10 parts of toluene , add 10 parts of ethylenic monomers containing 8-hydroxyquinoline ligand, stir and react at 100°C for 3 days, let stand for 1 day, filter the filtrate, add methanol to precipitate, filter to obtain a solid, recrystallize petroleum ether 3 times, A vinylic monomer containing an aluminum complex of 8-hydroxyqui...

Embodiment 3

[0034] 100 parts of hydroxyethyl methacrylate, added containing -CH 2 20 parts of 8-hydroxyquinoline with Cl substituent, under the catalysis of 1.5 parts of sodium acetate, 3 parts of p-hydroxyphenol as a polymerization inhibitor, the temperature is controlled at 100 ° C and stirred, and the reaction is controlled for 8 hours. After the reaction is completed, add 500 parts of water, drop Appropriate weight concentration is 5% dilute ammonia water to neutral, a white precipitate is obtained, petroleum ether is recrystallized 3 times, and alkene monomers containing 8-hydroxyquinoline ligands are obtained; 1 part of aluminum sulfate is dissolved in 50 parts of chloroform, and added 8 parts of ethylenic monomers containing 8-hydroxyquinoline ligand were stirred and reacted at 120°C for 3 days, then stood still for 1 day, filtered to obtain the filtrate, added water to precipitate, filtered to obtain a solid, and recrystallized petroleum ether 3 times to obtain -Alkenic monomers o...

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Abstract

The invention relates to a series of olefin monomer of multi-functional group 8-hydroxyquinoline metal complex, its preparation process and use thereof, wherein the preparation process consists of synthesizing alkene monomers containing 8-hydroxyquinoline, and compounding with metallic ions.

Description

technical field [0001] The present invention relates to a class of ethylenic monomer containing 8-hydroxyquinoline metal complex and its preparation method and application. In particular, it is an 8-hydroxyquinoline complex ethylenic monomer containing multiple polymerizable functional groups capable of forming a cross-linked polymer, and its preparation and use. technical background [0002] Organic / polymer electroluminescent devices have become a major research hotspot in the field of information display technology due to their advantages such as low driving voltage, easy realization of large-screen display, high brightness, wide viewing angle, and continuously adjustable luminous color. Since 1987, C.W.Tang of Kadak Company of the United States and his collaborators reported a kind of 8-hydroxyquinoline aluminum as the light-emitting layer, the driving voltage is less than 10 volts, and the luminous brightness reaches 1000cd / m 2 , Since the green-emitting electroluminesc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/30C07F5/00C07F3/00C09K11/06C07D215/20
Inventor 杜乃婴吕满庚梅群波
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI