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Method for preparing two 4-[(8-hydroxy-5-quinolinyl)azo] cadmium benzenesulfonate complexes with blue light performance

A technology of benzenesulfonic acid and blue light, which is applied in the direction of cadmium organic compounds, chemical instruments and methods, and luminescent materials, can solve the problems of low brightness and luminous efficiency of blue light organic luminescent materials, and achieve improved brightness and luminous efficiency and good film formation Features, strong effect of stability

Inactive Publication Date: 2013-04-24
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 blue light organic light-emitting materials; and provide a blue light organic light-emitting material and its preparation method

Method used

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  • Method for preparing two 4-[(8-hydroxy-5-quinolinyl)azo] cadmium benzenesulfonate complexes with blue light performance
  • Method for preparing two 4-[(8-hydroxy-5-quinolinyl)azo] cadmium benzenesulfonate complexes with blue light performance
  • Method for preparing two 4-[(8-hydroxy-5-quinolinyl)azo] cadmium benzenesulfonate complexes with blue light performance

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Experimental program
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specific Embodiment approach 1

[0017] Specific embodiment one: the blue light organic luminescent material {{Cd{4-[(8-hydroxyl-5-quinoline) azo]benzenesulfonic acid} (H 2 O) 2} H 2 O} n The molecular formula is C 15 h 15 N 3 CdO 7 S, whose structural formula is

[0018] 。

[0019] {{Cd{4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid}·(H 2 O) 2} H 2 O} n The steps of the preparation method are as follows: 1. Preparation of 4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid: p-aminobenzenesulfonic acid (1.221g, 7.06mol) was dissolved in 20mL H 2 O, add HCl solution (37%, 1.47mL), temperature 0-5 ℃. Add 5% NaNO dropwise 2 Solution (7.06 mmol, 10 mL), after stirring at 0-5 °C for 60 min, the diazonium reaction was completed, and 8-hydroxyquinoline (1.025 g, 7.06 mmol) was cooled and stirred in 0.5M NaOH solution (16 mL) until viscous , Add dropwise within 60min, and stir overnight at room temperature, adjust the pH to 7.5-8.0 (with diluted sodium acetate solution) and filter the precipitat...

specific Embodiment approach 2

[0029] Specific embodiment 2: In this embodiment, the blue light organic luminescent material {{Cd{4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid}·(H 2 O) 2} H 2 O} n The steps of the preparation method are as follows: 1. Preparation of 4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid: p-aminobenzenesulfonic acid (1.221g, 7.06mol) was dissolved in 20mL H 2 O, add HCl solution (37%, 1.47mL), temperature 0-5 ℃. Add 5% NaNO dropwise 2 Solution (7.06 mmol, 10 mL), after stirring at 0-5 °C for 60 min, the diazonium reaction was completed, and 8-hydroxyquinoline (1.025 g, 7.06 mmol) was cooled and stirred in 0.5M NaOH solution (16 mL) until viscous , Add dropwise within 60min, and stir overnight at room temperature, adjust the pH to 7.5-8.0 (with diluted sodium acetate solution) and filter the precipitate. The crude product was recrystallized twice in water (50 mL) and then dried in a vacuum oven (yield 40%).

[0030] 2. Add cadmium chloride (CdCl 2 2.5H 2 O (60mg, 0....

specific Embodiment approach 3

[0031] Specific embodiment three: In this embodiment, the blue light organic luminescent material {{Cd{4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid} (ethylenediamine)} ethanol} n The molecular formula is C 19 h 23 N 5 CdO 5 S, whose structural formula is

[0032] 。

[0033] {{Cd{4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid}·(ethylenediamine)}·ethanol} n The steps of the preparation method are as follows: 1. Preparation of 4-[(8-hydroxy-5-quinoline)azo]benzenesulfonic acid: p-aminobenzenesulfonic acid (1.221g, 7.06mol) was dissolved in 20mL H 2 O, add HCl solution (37%, 1.47mL), temperature 0-5 ℃. Add 5% NaNO dropwise 2 Solution (7.06 mmol, 10 mL), after stirring at 0-5 °C for 60 min, the diazonium reaction was completed, and 8-hydroxyquinoline (1.025 g, 7.06 mmol) was cooled and stirred in 0.5M NaOH solution (16 mL) until viscous , Add dropwise within 60min, and stir overnight at room temperature, adjust the pH to 7.5-8.0 (with diluted sodium acetate sol...

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Abstract

The invention discloses organic blue light emitting materials and a preparation method thereof, relating to organic light emitting materials and preparation methods thereof. The organic blue light emitting materials are used for solving the problems of low brightness and light emitting efficiency of the existing organic blue light emitting materials. The molecular formulae of the organic blue light emitting materials are C15H15N3CdO7S and C19H23N5CdO5S. The preparation method of the organic blue 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 cadmium chloride into a solvent, mixing and adding an organic base, 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 orange 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 blue light emitting materials prepared by the preparation method are all of blue fluorescence and have higher thermal stability and good film forming characteristics. The yield of the products prepared by the preparation method is high and can be more than 55%.

Description

technical field [0001] The invention relates to an organic luminescent material and a preparation method thereof, in particular to two cadmium 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 complexes containing cadmium, 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...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F3/08C07D215/38
Inventor 罗亚楠曲晓姝杨艳艳于晓洋曹雪玲于沛姜冬梅
Owner JILIN INST OF CHEM TECH
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