Method for preparing 8-hydroxyquinoline metal compounds

A hydroxyquinoline and compound technology, which is applied in the field of preparation of high-purity 8-hydroxyquinoline metal compounds, can solve the problems of many side reactions, low yield of 8-hydroxyquinoline, long production cycle and the like, and achieves improved production. efficiency and purity, avoid side reactions, and prevent environmental pollution

Active Publication Date: 2009-08-26
GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems existing in the current synthesis, the present invention aims to solve the problems of low yield of 8-hydroxyquinolines, many side reactions and long production cycle

Method used

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  • Method for preparing 8-hydroxyquinoline metal compounds
  • Method for preparing 8-hydroxyquinoline metal compounds
  • Method for preparing 8-hydroxyquinoline metal compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Aluminum isopropoxide is used as raw material to synthesize 8-hydroxyquinoline aluminum

[0032] Add 120mL toluene to a 500mL four-necked bottle, add aluminum isopropoxide to a four-necked bottle, fill with nitrogen and stir, completely dissolved, colorless and transparent. 8-Hydroxyquinoline was dissolved in 120mL toluene, added to the reaction through a constant pressure dropping funnel, and 8-Hydroxyquinoline solution was added dropwise, yellow-green color was produced immediately, and yellow precipitate was formed soon, and the 8-Hydroxyquinoline solution was completely added A large amount of precipitation was produced. The temperature was maintained at 60°C, and the heating was stopped after 30 minutes of reaction, cooled to room temperature, and filtered to obtain a large amount of fibrous solid. Wash twice with 150x2mL toluene; wash twice with 150x2mL petroleum ether, and dry in vacuum at 70°C for 6 hours to obtain 17.5 g of a bright yellow produc...

Embodiment 2

[0037] Embodiment 2: Synthesis of two (2-methyl-8-hydroxyquinoline)-4-(phenylphenoxy)aluminum

[0038] Add 4-phenylphenol and 200ml of toluene into a 1L four-neck flask, fill with nitrogen and stir to completely dissolve. Dissolve aluminum isopropoxide in 120ml of toluene, add dropwise, white turbidity will appear immediately, complete addition in 1.5 hours, and stir for 1 hour. When 2-methyl-8-hydroxyquinoline was added dropwise, yellow-green turbidity immediately appeared. It took 1 hour to complete the addition, and refluxed for 16 hours after the addition. A slightly yellow solid precipitated after cooling, and was filtered to obtain a white solid. Purified with toluene and dried, the yield was 80%.

Embodiment 3

[0039] Embodiment 3: 8-hydroxyquinolate lithium is synthesized

[0040] Add 120ml of dichloromethane into a 250ml four-necked bottle, first add hydrated lithium hydroxide, and stir until it becomes white and turbid. 8-Hydroxyquinoline was added in batches, and milky yellow was produced in less than half a minute; soon the milky yellow increased, and reacted overnight at 25°C to obtain a large amount of light yellow solid. A large amount of milky yellow solid was obtained by filtration, washed twice with 100 ml of dichloromethane at 200°C for 24 hours, and the yield was 90%.

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Abstract

The invention relates to a method for preparing 8-hydroxyquinoline metal compounds, in particular to a synthesis method for organic electroluminescent materials. A method for the preparation of a compound of Mqnqm', in which M is Al, Li; n is 1 to 3, m is 0-2, q is 8-hydroxyquinoline and derivatives thereof, and q' is a ligand different from q, comprises the steps of: using a hydrophobic solvent, formulating industrial ligand to a solution for being dropped into a reaction vessel, stirring at certain temperature to obtain high-purity products. By using the hydrophobic solvent, the invention can implement the reaction efficiently, shorten reaction period, avoid complicated operation and purification procedures, enhance yield and purity of the product, reduce environmental pollution and lower the cost, besides, the resultant mother liquid can be reused. The technology can be popularized to the preparation of other 8-hydroxyquinoline metal compounds, and the resultant product can serve as an electroluminescent material or an electronic transmission material.

Description

technical field [0001] The invention relates to a synthesis method of an organic electroluminescence material, in particular to a preparation method of a high-purity 8-hydroxyquinoline metal (Al, Li) compound. technical background [0002] In 1987, Deng Qingyun and others from Kodak Company of the United States used Alq 3 A sandwich-type double-layer organic electroluminescent device was successfully prepared using aromatic diamine as the light-emitting layer and the hole-transporting layer (Tang C.W., et al. Applied Physics Letters, 1987, 51, 913). In 1990, Burroughes J.H., et al. of the University of Cambridge, UK developed organic polymer light-emitting diodes (Burroughes J.H., et al. Nartue, 1990, 347, 5395). These major breakthroughs greatly promoted the development of the field of organic electroluminescent technology. Since then, scientists from various countries have invested a lot of energy in research and development, and more and more organic electroluminescent m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/26C07F5/06C07F1/02C09K11/06
CPCH05B33/14C09K11/06C07D215/30C09K2211/186C07F5/06C07F1/02
Inventor 戴雷蔡丽菲赵洪玉
Owner GUANGDONG AGLAIA OPTOELECTRONICS MATERIALS
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