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Electroluminescent material, preparation method and application thereof

An electroluminescent material and reaction technology, applied in the direction of organic chemistry, etc., can solve the problems of not getting the expected color coordinates, weak electron-withdrawing ability, strong electron-withdrawing ability, etc. The effect of large flat structures

Active Publication Date: 2022-07-26
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 application thereof
  • Electroluminescent material, preparation method and application thereof
  • Electroluminescent material, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 Preparation of 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. After stirring for 12 hours at room temperature, the reaction was stopped and the reaction was quenched with water. , extracted with dichloromethane and dried with anhydrous magnesium sulfate. After the solution was concentrated, a yellow liquid was obtained, which was purified by silica gel column chromatography with a mixed solvent of petroleum ether / dichloromethane (7 / 1, v / v) as elution agent, the yield was 84%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis 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-dioxaboran-2-yl)benzoic acid ethyl ester

[0049] Under the protection of inert gas, ethyl 2-bromobenzoate (17.5g, 76.4mmol) was dissolved in 250ml of anhydrous tetrahydrofuran, and the n-butyllithium solution (38.2ml of 2.4mol / L) in n-hexane was slowly added dropwise. , 91.7 mmol), after stirring for 1 hour at room temperature, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (25.6g) was added to the reaction system , 0.14mol), stopped the reaction, quenched the reaction with water, extracted with dichloromethane and dried with anhydrous magnesium sulfate, the solution was concentrated to obtain a khaki liquid, which was purified by silica gel column chromatography, mixed with petroleum ether / dichloromethane Solvent (5 / 1, v / v) as eluent gave a white solid in 87% yield. 1 H NMR, 13 The results of CNMR, MS and elemental analysis show that the obtained compound is the target product, and the chemical reaction...

Embodiment 3

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

[0052] Under an argon atmosphere, into a 500 mL three-necked flask, add ethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)benzoic acid ethyl ester (8.4g, 30.4mmol), 2,7-dibromo-S,S-dioxydibenzophenone (20.0g, 45.6mmol), tetrabutylamine bromide (0.49g, 1.52mmol), catalyst triphenyl Palladium phosphine dichloride (1.76 g, 1.52 mmol) and 200 mL of toluene were heated with stirring. When the temperature was stable at 110 °C, an organic base (20 mL) and K were added. 2 CO 3 (41.95g, 0.30mol) aqueous solution 42mL, reacted for 12h. After concentrating the reaction solution, it was purified by silica gel column chromatography, and a mixed solvent of petroleum ether and dichloromethane (3 / 1, v / v) was used as the eluent to obtain a pale yellow solid with a yield of 75%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis show that the obtained compound is the targe...

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Abstract

The invention discloses a class of electroluminescent materials and a preparation method and application thereof. Among them, the thioxafluorene unit is a seven-membered condensed ring structure, and the better planarity is conducive to the injection and transport of carriers, and improves the optoelectronic properties of the material; , which is beneficial to improve the thermal resistance of the material and meet the practical needs of the material. The present invention obtains the electroluminescent material based on the thioxafluorene unit through Suzuki coupling reaction, Ullman coupling reaction, still coupling reaction, etc., and has good solubility, and can be dissolved in common organic solvents, The light emitting layer of the light emitting diode is prepared by spin coating, ink jet printing or film formation.

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 a preparation method and application thereof. Background technique [0002] The electronic or optoelectronic industries such as organic / material light-emitting diodes, organic field-effect transistors, and organic solar cells have developed rapidly. Among them, products based on organic light-emitting diodes (OLEDs) have long been available. However, due to the current vacuum evaporation process used to prepare OLED devices, Equipment is expensive. The material utilization rate is low (~20%), which keeps the price of OLED products high. Solution processing technology can make up for the shortcomings of vacuum evaporation, and gradually attract the attention of scientific research institutions and company manufacturers. The material has the advantages of good film formation and machinability, and is suitable...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/78
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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