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Preparation methods of two copper complexes of 4-[(8-hydroxy-5-quinoline)azo]benzenesulfonate with purple properties

A technology of benzenesulfonic acid and purple light, which is applied in the direction of copper organic compounds, chemical instruments and methods, and luminescent materials, can solve the problems of low brightness and luminous efficiency of purple light organic light-emitting materials, and achieve improved brightness and luminous efficiency and high yield , Good film-forming properties

Inactive Publication Date: 2015-08-26
JILIN INST OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the problem of low brightness and luminous efficiency of the existing purple light organic light-emitting materials; and to provide a purple light organic light-emitting material and its preparation method

Method used

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  • Preparation methods of two copper complexes of 4-[(8-hydroxy-5-quinoline)azo]benzenesulfonate with purple properties
  • Preparation methods of two copper complexes of 4-[(8-hydroxy-5-quinoline)azo]benzenesulfonate with purple properties
  • Preparation methods of two copper complexes of 4-[(8-hydroxy-5-quinoline)azo]benzenesulfonate with purple properties

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Experimental program
Comparison scheme
Effect test

specific Embodiment approach

[0017] Specific implementation mode: Specific implementation mode one: the purple organic luminescent material {Cu{4-[(8-hydroxyl-5-quinoline)azo]benzenesulfonic acid} (ethylenediamine)} in this embodiment mode 0.5 h 2 The molecular formula of O is C 34 h 36 N 10 Cu 2 o 9 S 2 , whose structural formula is.

[0018]

[0019] {Cu{4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid}·(ethylenediamine)}·0.5H 2 The steps of O preparation method are as follows: One, the preparation of 4-[(8-hydroxy-5-quinoline) azo] benzenesulfonic acid: 1.221g p-aminobenzenesulfonic acid is dissolved in 20mL water, adds 37% hydrochloric acid solution 1.47 mL, the reaction temperature is 0-5°C, then 10mL of 5% sodium nitrite solution is added dropwise, and the diazotization is completed after stirring at 0-5°C for 60 minutes, and 1.025g of 8-hydroxyquinoline is dissolved in 16mL0 Cool and stir in 5M sodium hydroxide solution until viscous, add dropwise within 60 minutes, and stir overnight ...

specific Embodiment approach 2

[0029] Specific embodiment two: In this embodiment, the purple light organic light-emitting material {Cu{4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid} (ethylenediamine)} 0.5H 2 The steps of O preparation method are as follows: One, the preparation of 4-[(8-hydroxyl-5-quinoline) azo] benzenesulfonic acid: 1.221g p-aminobenzenesulfonic acid is dissolved in 20mL water, adds 37% hydrochloric acid solution 1.47 mL, the reaction temperature is 0-5°C, then 10mL of 5% sodium nitrite solution is added dropwise, and the diazotization is completed after stirring at 0-5°C for 60 minutes, and 1.025g of 8-hydroxyquinoline is dissolved in 16mL0 Cool and stir in 5M sodium hydroxide solution until viscous, add dropwise within 60 minutes, and stir overnight at room temperature, adjust the pH to 7.5-8.0 with diluted sodium acetate solution, filter the precipitate, and dissolve the crude product in 50mL of water Recrystallized twice, and then dried in a vacuum oven, the yield was 40%; 2. Ad...

specific Embodiment approach 3

[0030] Specific embodiment three: In this embodiment, the purple light organic light-emitting material {Cu{4-[(8-hydroxyl-5-quinoline)azo]benzenesulfonic acid} 2}[Cu(Ethylenediamine) 2 ]·2H 2 The molecular formula of O is C 34 h 38 N 10 Cu 2 o 10 S 2 , whose structure is

[0031] .

[0032] {Cu{4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid} 2}[Cu(Ethylenediamine) 2 ]·2H 2 The steps of O preparation method are as follows: One, the preparation of 4-[(8-hydroxy-5-quinoline) azo] benzenesulfonic acid: 1.221g p-aminobenzenesulfonic acid is dissolved in 20mL water, adds 37% hydrochloric acid solution 1.47 mL, the reaction temperature is 0-5°C, then 10mL of 5% sodium nitrite solution is added dropwise, and the diazotization is completed after stirring at 0-5°C for 60 minutes, and 1.025g of 8-hydroxyquinoline is dissolved in 16mL0 Cool and stir in 5M sodium hydroxide solution until viscous, add dropwise within 60 minutes, and stir overnight at room temperature, adj...

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Abstract

The invention discloses organic purple light emitting materials and a preparation method thereof, relating to organic light emitting materials and preparation methods thereof. The organic purple light emitting materials are used for solving the problems of low brightness and light emitting efficiency of the existing organic purple light emitting materials. The molecular formulae of the organic purple light emitting materials are C34H36N10Cu2O9S2 and C34H38N10Cu2O9S2. The preparation method of the organic purple light emitting materials comprises the following steps of: (1) preparing 4-[(8-hydroxy-5-quinolinyl)azo] benzenesulfonic acid; and (2) preparing coordination polymers: respectively dissolving ligand and cupric chloride into a solvent, mixing and adding quadrol, stirring for 1 hour at room temperature, putting a mixture in a reaction kettle with a polytetrafluoroethylene inner liner, and carrying out temperature programming to 100 DEG C for 100 hours, thereby obtaining dark brown flaky crystals. The products prepared by the preparation method disclosed by the invention are single crystals with intact crystal forms; and shown by light emitting performance tests, the organic purple light emitting materials prepared by the preparation method are all of purple fluorescence and have higher thermal stability and good film forming characteristics. The yield of the products prepared by the preparation method is high and is more than 55%.

Description

technical field [0001] The invention relates to an organic luminescent material and a preparation method thereof, in particular to two copper complexes of 4-[(8-hydroxyl-5-quinoline)azo]benzenesulfonate and a preparation method thereof. Background technique [0002] Because of the good properties and potential application prospects of the luminescent complexes containing azo ligands in sensor technology, photochemistry and electroluminescence materials, etc., they have attracted much attention and become a research hotspot. The researchers synthesized a large amount of d 10 family of metal complexes containing azo ligands, especially copper-containing complexes, and studied their luminescent properties. It was found that the size of the ligand π-conjugated system and the influence of the electrons of the ligand substituents are the key factors to adjust the luminescent properties of the complexes. An important factor; for example, in 2010, X. Feng et al. reported a series o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08C09K11/06
Inventor 罗亚楠于晓洋曹雪玲于丽影曲晓姝崔立棚孙双双
Owner JILIN INST OF CHEM TECH