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A kind of electroluminescent material based on anthracene derivative and its preparation method and application

A technology of electroluminescent materials and anthracene derivatives, applied in the directions of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of difficult to form amorphous films, reduce the optoelectronic properties of devices, restrict development, etc., and achieve high-efficiency and stable device performance, Improve solubility and thermal stability

Active Publication Date: 2020-05-22
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the small molecular material of anthracene is easy to crystallize, and it is not easy to form an amorphous film; and the planarity of the anthracene unit is prone to molecular stacking, resulting in fluorescence quenching, thereby reducing the optoelectronic performance of the device and limiting its further development in the optoelectronic field.

Method used

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  • A kind of electroluminescent material based on anthracene derivative and its preparation method and application
  • A kind of electroluminescent material based on anthracene derivative and its preparation method and application
  • A kind of electroluminescent material based on anthracene derivative and its preparation method and application

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Experimental program
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Effect test

preparation example Construction

[0052] Preparation of an anthracene derivative monomer

[0053] Preparation of ethylthiophene-3-carboxylate

[0054] In a 500mL three-necked flask, thiophene-3-carboxylic acid (12.8g, 0.1mol) was dissolved in 200mL of methanol, and 20mL of concentrated sulfuric acid (98wt%) was added dropwise to the reaction solution, and after stirring at room temperature for 12 hours, the reaction was stopped. 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. The mixed solvent of petroleum ether / dichloromethane (5 / 1, v / v ) is the eluting agent, and the productive rate is 73%. 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:

[0055]

[0056] Preparation of ethyl 2-(tribu...

Embodiment 1

[0072] The preparation of embodiment 1 compound B1

[0073] Under argon atmosphere, in a 100mL three-necked flask, add 2,9-dibromo-7,7,14,14-tetrabutyl-7,14-dihydroperylene[1,2-b:7,8 -b']dithiophene (1.80g, 2.4mol), bis(9,9-dimethyl-9H-fluoren-2-yl)amine (2.02g, 5.0mmol), sodium tert-butylate (1.84g, 19.2mmol), palladium acetate (27mg, 0.12mmol) and 50ml toluene. Heat and stir to 85°C, add 0.12ml of tri-tert-butylphosphine in toluene (0.24mmol, 2mol / L), and react for 12h. After the reaction was stopped, the solvent was concentrated, and the crude product was purified by column chromatography using a mixed solvent of petroleum ether and dichloromethane (2 / 1, v / v) as the eluent to obtain a green solid, which was named compound B1. 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:

[0074]

[0075] The differential scanning calorimetry (DSC)...

Embodiment 2

[0078] The synthesis of embodiment 2 compound B2

[0079]Under argon atmosphere, in a 100mL three-necked flask, add 2,9-dibromo-7,7,14,14-tetrabutyl-7,14-dihydroperylene[1,2-b:7,8 -b']dithiophene (1.80g, 2.4mol), N-[1,1-biphenyl]-4-yl-9,9-dimethyl-9H-fluorene-3-amine (1.81g, 5.0mmol ), sodium tert-butylate (1.84g, 19.2mmol), palladium acetate (27mg, 0.12mmol) and 50ml of toluene. Heat and stir to 85°C, add 0.12ml of tri-tert-butylphosphine in toluene (0.24mmol, 2mol / L), and react for 12h. After stopping the reaction, the solvent was concentrated, and the crude product was purified by column chromatography, using a mixed solvent of petroleum ether and dichloromethane (3 / 1, v / v) as the eluent, and finally a green solid was obtained, which was named compound B2. 1 H NMR, 13 C NMR, MS and elemental analysis results show that the compound obtained is the target product, and the chemical reaction equation of the preparation process is as follows:

[0080]

[0081] The differe...

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Abstract

The invention discloses an anthracene derivative-based electroluminescent material, a preparation method and application thereof. The electroluminescent material based on anthracene derivatives has a seven-membered condensed ring structure, and its better planarity is conducive to the injection and transport of carriers, improving the photoelectric performance of the material; the ring structure makes the anthracene derivatives have better Rigidity is conducive to improving the heat resistance of the material and meeting the practical needs of the material. The present invention obtains the electroluminescent material based on anthracene derivatives through Suzuki coupling reaction, Ullmann coupling reaction, still coupling reaction, etc., the electroluminescent material has good solubility, and can use common organic The solvent is dissolved, and the light-emitting layer of the light-emitting diode is prepared by spin coating, ink-jet printing or printing to form a film.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to an anthracene derivative-based electroluminescent material and its preparation method and application. 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 already come out, but because the current preparation of OLED devices uses a vacuum evaporation process, instruments Equipment is 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 machinabi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/06C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D495/06C09K2211/1044C09K2211/1092C09K2211/1011H10K85/626H10K85/6572H10K85/6576H10K50/11
Inventor 应磊郭婷胡黎文彭俊彪
Owner SOUTH CHINA UNIV OF TECH
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