Electroluminescence material based on anthracene derivatives as well as preparation method and application thereof

A technology of electroluminescent materials and anthracene derivatives, which is applied in the direction of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of restricting development, reducing the photoelectric performance of devices, and not being easy to form amorphous films, so as to improve solubility and activity The effect of many sites, high efficiency and stable device performance

Active Publication Date: 2018-08-03
SOUTH CHINA UNIV OF TECH
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  • Summary
  • 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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  • Electroluminescence material based on anthracene derivatives as well as preparation method and application thereof
  • Electroluminescence material based on anthracene derivatives as well as preparation method and application thereof
  • Electroluminescence material based on anthracene derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
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, and finally a green solid was obtained, 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 ...

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 electroluminescence material based on anthracene derivatives as well as a preparation method and application thereof. The electroluminescence material based on the anthracene derivatives is of a 7-membered condensed ring structure; better planarity is realized; the injection and the transmission of current carriers are facilitated; the photoelectric performance of the material is improved; through a fused ring structure, the anthracene derivatives have good rigidity; the heat-resistant capability of the material is favorably improved; the practical requirements of the material are met. Through Suzuki coupling reaction, Uhlmann coupling reaction, still coupling reaction and the like, the electroluminescence material based on anthracene derivatives is obtained; theelectroluminescence material has good dissolution performance; the common organic solvent dissolution is used; a film is formed through rotary coating, ink printing or printing film forming; a luminous layer of a light emitting diode is obtained through preparation.

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 Applications(China)
IPC IPC(8): C09K11/06C07D495/06H01L51/50H01L51/54
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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