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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 to compounds containing elements of Group 1/11 of the periodic table, compounds containing elements of Group 3/13 of the periodic table, compounds of elements of Group 2/12 of the periodic table, etc. , can solve the problems of poor film formation, complex preparation process, uneven dispersion, etc., and achieve the effect of improving luminous efficiency, high luminous efficiency, and good solubility

Inactive Publication Date: 2005-01-26
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

At present, there are the following types of luminescent materials, which have the following disadvantages: 1. Organic small molecule electroluminescent materials, crystallization phenomenon exists in the preparation and operation of devices, which reduces the life of electroluminescent devices. At the same time, the preparation of organic small molecule EL materials The method of the device mainly depends on vacuum evaporation, the preparation process is complicated, and the production cost is high; 2 The conjugated polymer has a complicated preparation process, the solubility is not ideal, and the processing is difficult; 3 The polymer doped with metal-organic complexes is prone to phase separation, Uneven dispersion, reduced material performance, reduced fluorescence intensity, and reduced fluorescence lifetime; 4. There are many synthetic methods for polymer metal complex luminescent materials, which mainly have shortcomings such as crosslinking, poor solubility, and poor film-forming properties, which cannot meet the requirements of excellent preparation performance. electroluminescent devices
At present, there are few studies on the synthesized high molecular weight 8-hydroxyquinoline metal complexes. Most of the high molecular weight 8-hydroxyquinoline metal complexes reported in the literature have poor solubility and film-forming properties. When the metal complex accounts for up to 20% of the weight of the polymer, the polymer is difficult to dissolve in common solvents

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 100 parts of allyl alcohol, add -CH2 5 parts of 8-hydroxyquinoline with Cl substituent, under the catalysis of 0.01 part of sodium hydroxide, 0.1 part of p-hydroxyphenol as a polymerization inhibitor, the temperature is controlled at 40 ° C and stirred, the reaction is controlled for 48 hours, and 500 parts of water are added after the reaction is completed. Add an appropriate amount of dilute ammonia water with a weight concentration of 1% to neutrality to obtain a white precipitate, recrystallize petroleum ether 3 times to obtain an alkene monomer containing 8-hydroxyquinoline ligand; take 1 part of aluminum isopropoxide and dissolve it in 10 1 part of toluene, add 2.5 parts of 8-hydroxyquinoline, stir and react at room temperature for 1 day, add 1.2 parts of ethylenic monomers containing 8-hydroxyquinoline ligand, stir and react at room temperature for 3 days, let stand for 1 day, and filter to obtain The filtrate was evaporated to remove the solvent, and petroleum et...

Embodiment 2

[0035] 100 parts of p-vinylbenzyl chloride, add -CH 2 5 parts of 8-hydroxyquinoline with OH substituent, under the catalysis of 0.05 part of sodium acetate, 0.5 part of benzoquinone as a polymerization inhibitor, the temperature is controlled at 60 ° C and stirred, and the reaction is controlled for 24 hours. After the reaction is completed, 200 parts of water are added, and an appropriate amount is added dropwise 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, 2.5 parts of 8- Hydroxyquinoline was dissolved in 60 parts of absolute ethanol, stirred and reacted at room temperature for 3 days, allowed to stand for 1 day, added 6 parts of ethylenic monomers containing 8-hydroxyquinoline ligand, stirred and reacted for 10 days at room temperature, allowed to stand for 1 day day, filtered...

Embodiment 3

[0037] 100 parts of hydroxyethyl methacrylate, added containing -CH 2 5 parts of 8-hydroxyquinoline with Cl substituent, under the catalysis of 0.1 part of sodium acetate, 1 part of p-hydroxyphenol as a polymerization inhibitor, the temperature is controlled at 80 ° C and stirred, and the reaction is controlled for 10 hours. After the reaction is completed, add 1000 parts of water, drop An appropriate amount of dilute ammonia water with a weight concentration of 5% 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 aluminum chloride is dissolved in 45 parts of chloroform , 2.1 parts of 8-hydroxyquinoline, stirring and reacting at room temperature for 6 days, standing for 1 day, adding 4 parts of ethylenic monomers containing 8-hydroxyquinoline ligands, stirring and reacting for 8 days at room temperature, standing for 1 day, The filtrate was obtained by fil...

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Abstract

The invention relates to a series of olefin monomer of a polymerisable functional group 8-hydroxyquinoline metal complex, its preparation process and use thereof, wherein the preparation process consists of synthesizing alkene monomers containing 8-hydroxyquinoline through reaction between vinyl compound containing reacting function group with modified 8-hydroxyquinoline, then compounding with metallic ions and 8-hydroxyquinoline.

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 olefinic monomer capable of being polymerized with other types of olefins to form a linear copolymer, an 8-hydroxyquinoline metal complex containing a polymerizable functional group, and its preparation method and use. technical background [0002] With the advent of the information age, new, high-efficiency, and light-weight organic electroluminescent flat-panel displays (OLEDs) have attracted more and more attention, and have become a research hotspot at home and abroad in recent years. As the whole society pays more attention to health, environmental protection, resources and energy utilization, people put forward higher and higher requirements for luminescent materials. Especially for the production of luminescent materials with special processing properties and special photoe...

Claims

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Application Information

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IPC IPC(8): C07D215/20C07F1/00C07F3/00C07F5/00
Inventor 杜乃婴吕满庚梅群波
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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