Electroluminescent material, preparation method and applications thereof

An electroluminescent material and luminescent technology, applied in the direction of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of not getting the expected color coordinates, weak electron-absorbing ability, strong electron-absorbing ability, etc., and reach the active site More points, stable molecular structure, good solubility effect

Active Publication Date: 2019-06-04
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the S, S-dioxy-dibenzothiophene unit has a strong electron-withdrawing ability, and organic electroluminescent materials containing S, S-dioxy-dibenzothiophene units will have obvious intramolecular interactions, resulting in spectral red Shift, can not get the expected color coordinates of the material
Therefore, it is necessary to study new blue light units that have the advantages of S,S-dioxo-dibenzothiophene but have a weaker electron-withdrawing ability.

Method used

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  • Electroluminescent material, preparation method and applications thereof
  • Electroluminescent material, preparation method and applications thereof
  • Electroluminescent material, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation of embodiment 1 ethyl 2-bromobenzoate

[0046] In a 500mL three-necked flask, 2-bromobenzoic acid (20.1g, 0.1mol) was dissolved in 200ml of ethanol, and 20ml of concentrated sulfuric acid was added dropwise to the reaction solution, and after stirring at room temperature for 12 hours, the reaction was stopped, and the reaction was quenched with water , extracted with dichloromethane and dried with anhydrous magnesium sulfate, the solution was concentrated to obtain a yellow liquid, which was purified by silica gel column chromatography, and the mixed solvent of petroleum ether / dichloromethane (7 / 1, v / v) was eluting agent, yield 84%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:

[0047]

Embodiment 2

[0048] Example 2 Preparation of ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) ethyl benzoate

[0049] Under the protection of an inert gas, ethyl 2-bromobenzoate (17.5g, 76.4mmol) was dissolved in 250ml of anhydrous tetrahydrofuran, and a concentration of 2.4mol / L of n-butyllithium in n-hexane (38.2ml , 91.7mmol), after stirring at room temperature for 1 hour, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (25.6g , 0.14mol), stop the reaction, quench the reaction with water, extract with dichloromethane and dry with anhydrous magnesium sulfate, get a khaki liquid after the solution is concentrated, purify by silica gel column chromatography, the mixing of petroleum ether / dichloromethane The solvent (5 / 1, v / v) was used as eluent, and a white solid was obtained with a yield of 87%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction equation of the preparation process is as follows:

...

Embodiment 3

[0051] Example 3 Preparation of diethyl 2,2'-(5,5-dioxodibenzo[b,d]phenyl-3,7-yl)bis(benzene-3-carboxylate)

[0052] Under an argon atmosphere, add ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl benzoate to a 500mL three-necked flask (8.4g, 30.4mmol), 2,7-dibromo-S,S-dioxodibenzophenone (20.0g, 45.6mmol), tetrabutylammonium bromide (0.49g, 1.52mmol), catalyst triphenyl Phosphine palladium dichloride (1.76g, 1.52mmol) and 200mL toluene were stirred and heated, and when the temperature was stabilized at 110°C, an organic base (20mL) and K 2 CO 3 (41.95g, 0.30mol) aqueous solution 42mL, reacted for 12h. After the reaction solution was concentrated, it was purified by silica gel column chromatography, using a mixed solvent of petroleum ether and dichloromethane (3 / 1, v / v) as eluent, to obtain a light yellow solid with a yield of 75%. 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and the chemical reaction ...

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Abstract

The invention discloses a class of electroluminescent materials, a preparation method and applications thereof. According to the present invention, the sulfur oxygen fluorine and benzene unit is a seven-membered fused ring structure, wherein the good planarity easily achieves the injection and transport of carriers, and improves the photoelectric properties of the material; the bicyclic structurecan make the sulfur oxygen fluorine and benzene unit have good rigidity so as to easily improve the heat resistance of the material and meet the practical needs of the materials; and the electroluminescent material based on the sulfur oxygen fluorine and benzene unit and obtained through Suzuki coupling reaction, Ullmann coupling reaction, still coupling reaction and the like has good solubility,can be dissolved with common organic solvents, can form a film through spin coating, ink jet printing or printing, and can be prepared into the light emitting layer of light-emitting diodes.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a class of electroluminescent materials and their preparation methods and applications. Background technique [0002] Organic / material light-emitting diodes, organic field-effect transistors, organic solar cells and other electronic or optoelectronic industries have developed rapidly. Among them, products based on organic light-emitting diodes (OLEDs) have long been available, but because the current preparation of OLED devices uses a vacuum evaporation process, Instruments and equipment are expensive. The material utilization rate is low (~20%), which makes the price of OLED products remain high. Solution processing technology can make up for the deficiency of vacuum evaporation, and gradually attracts the attention of scientific research institutions and companies. The material has the advantages of good film-forming properties and machinability, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D333/78C07D409/14H01L51/54H01L51/50
Inventor 应磊胡黎文黄飞曹镛
Owner 东莞伏安光电科技有限公司
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