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Method for preparing 8-hydroxyquinoline metal compounds

一种羟基喹啉、化合物的技术，应用在高纯度8-羟基喹啉类金属化合物的制备领域，能够解决副反应多、8-羟基喹啉产率低、生产周期长等问题，达到提高产率和纯度、避免副反应、防止环境污染的效果

Active Publication Date: 2013-05-01
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 150×2mL of toluene; wash twice with 150×2mL of petroleum ether, and dry in vacuum at 70°C for 6 hours to obtain 17.5g of a bright yellow p...

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

This invention, which involves “the preparation method of 8-hydroxyquinoline metallic compound”, is a synthetic method of organic electroluminescent materials. The preparation method of compound Mqnqm′ is to add solution prepared by Zengshui solvent and industrial ligand into reaction vessel, stir it at a certain temperature, and then achieve high-purity product, as for the Mqnqm′, M stands for Al, Li, n stands for 1-3, m is 0-2, q is 8-hydroxyquinoline and its derivatives, and q′ is ligand different from q. Zengshui solvent is adopted in this invention which can react effectively and thus reducing reaction time and avoiding cumbersome operation and the refining process; this invention also increases total yield and purity, the mother liquor obtained can be recycled, which reduces environment pollution and cost as well. This technology can also spread to the preparation of other 8-hydroxyquinoline metallic compound and the product achieved can be used as electroluminescent materials or electron-transport materials.

Description

technical field [0001] The present invention relates to the synthesis method of organic electroluminescent material, particularly relates to a kind of preparation method of 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(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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