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Method for polymerizing 8-hydroxyquinoline metal complex

A technology of metal complexes and hydroxyquinoline, which is applied in the field of synthesis of organic macromolecular metal complexes, can solve the problems of complex preparation process, difficult film formation, easy phase separation and the like, and achieves the effect of broad application prospects.

Inactive Publication Date: 2012-10-03
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the small molecule 8-hydroxyquinoline metal complex as a light-emitting material has complex device preparation processes, difficulty in film formation, and prone to lattice changes or crystallization, resulting in a decrease in device stability and a reduction in the life of the electroluminescent device.
Even if it is doped into polymers, due to poor compatibility, the dispersion of metal complexes in the polymer matrix is ​​poor, and phase separation is easy to occur, which seriously affects the luminescence performance and life of the material [Mei Q B, Du N Y, Lu M G. European Polymer Journal, 2007, 43:2380-2386.]

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) The synthesis method of 5-bromo-8-tert-butoxycarbonyloxyquinoline is: take 3.94g (17.59mmol) of 5-bromo-8-hydroxyquinoline, and follow the steps of 5-bromo-8-hydroxyquinoline, Di-tert-butyl dicarbonate and 4-dimethylaminopyridine are taken by weighing di-tert-butyl dicarbonate and 4-dimethylaminopyridine in a molar ratio of 1: 1: 0.05, and 5-bromo-8-hydroxyquinoline, Di-tert-butyl dicarbonate and 4-dimethylaminopyridine were added to 500ml of n-hexane, the reaction temperature was controlled at 25°C, the reaction time was 6h, the reaction liquid was filtered, and the filtrate was recrystallized in n-hexane after removing the solvent by rotary evaporation .

[0027] (2) The synthesis method of 5-trimethylsilylethynyl-8-tert-butoxycarbonyloxyquinoline is: under the protection of anhydrous and oxygen-free nitrogen, add 5-bromo-8-tert-butoxyquinoline to the reaction flask Carbonyloxyquinoline 4.428g (13.67mmol), add reaction solvent 55ml (triethylamine / tetrahydrofuran,...

Embodiment 2

[0033] (1) The synthetic method of 5-bromo-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0034] (2) The synthesis method of 5-trimethylsilylethynyl-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0035] (3) The synthetic method of 5-ethynyl-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0036] (4) The synthesis method of polystyrene whose end group is 8-tert-butoxycarbonyloxyquinolyl is as follows: under the protection of anhydrous and oxygen-free nitrogen, add 2.9 g of azidopolystyrene (number The average molecular weight is 2310, PDI=1.12) and N,N-dimethylformamide 11ml, according to azidopolystyrene, 5-ethynyl-8-tert-butoxycarbonyloxyquinoline, cuprous bromide, Add 5-ethynyl-8-tert-butoxycarbonyloxyquinoline, cuprous bromide and PMDETA in the ratio of PMDETA molar ratio 1:1.5:1:1. The reaction temperature was controlled at 50℃, and the reaction time was 30h. After the reaction, the reaction mixture was over neutral Al 2 o 3 ...

Embodiment 3

[0040] (1) The synthetic method of 5-bromo-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0041] (2) The synthesis method of 5-trimethylsilylethynyl-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0042] (3) The synthetic method of 5-ethynyl-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0043] (4) The synthesis method of polystyrene whose terminal group is 8-tert-butoxycarbonyloxyquinolyl is as follows: under the protection of anhydrous and oxygen-free nitrogen, add 3.4 g of azidopolystyrene (number The average molecular weight is 4930, PDI=1.10) and N,N-dimethylformamide 13ml, according to azidopolystyrene, 5-ethynyl-8-tert-butoxycarbonyloxyquinoline, cuprous bromide, Add 5-ethynyl-8-tert-butoxycarbonyloxyquinoline, cuprous bromide and PMDETA in the ratio of PMDETA molar ratio 1:1.2:1:1. The reaction temperature was controlled at 70℃, and the reaction time was 20h. After the reaction, the reaction mixture was over neutral Al 2 ...

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Abstract

The invention provides a method for polymerizing an 8-hydroxyquinoline metal complex, which comprises the following steps: synthesizing 5-bromo-8-tert-butoxycarbonylquinoline;synthesizing 5-trimethylsilylacetylene-8-tert-butoxycarbonylquinoline by the Sonagashira coupling reaction between 5-bromo-8-tert-butoxycarbonylquinoline and trimethylsilylacetylene; synthesizing 5-acetenyl-8-tert-butoxycarbonylquinoline by an elimination reaction; synthesizing polystyrene of which terminal group is 8-tert-butoxycarbonylquinoline by the click reaction between 5-bromo-8-tert-butoxycarbonylquinoline and azido-polystyrene; synthesizing polystyrene macromolecular ligand of which the terminal group is 8-hydroxyquinolinyl; and synthesizing a polystyrene metal complex by the coordination reaction between polystyrene macromolecular ligand of which the terminal group is 8-hydroxyquinolinyl, 8-hydroxyquinoline and metal ions. The polymer metal complex synthesized by the method of the invention shows a wide application prospect in the fields of electroluminescence, magnetic functional polymer, electrochemical catalysis and polymer photovoltaic devices.

Description

technical field [0001] The present invention relates to a method for synthesizing an organic macromolecular compound, and mainly relates to a method for synthesizing an organic macromolecular metal complex. Background technique [0002] Generally, organic electroluminescent materials can be divided into three categories: metal-organic complex materials, organic small molecule materials and organic polymer materials. Among metal-organic complex materials, 8-hydroxyquinoline metal complexes are considered to be the first choice for the commercialization of organic electroluminescent devices due to their high electron transport properties and high fluorescence in the solid state. However, small molecule 8-hydroxyquinoline metal complexes as light-emitting materials have complex device preparation processes, difficulty in film formation, and prone to crystal lattice changes or crystallization, resulting in decreased device stability and reduced life of electroluminescent devices...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F112/14C08F8/42
Inventor 张春红张爽苏广东王海伦耿倩倩
Owner HARBIN ENG UNIV
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