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A class of electroluminescent materials containing polar substituent group anthracene derivatives and its preparation method and application

A technology of electroluminescent materials and polar substituents, applied in the direction of luminescent materials, chemical instruments and methods, circuits, etc., can solve the problems of reducing the photoelectric performance of devices, not easy to form amorphous films, and restricting development

Active Publication Date: 2020-06-05
东莞伏安光电科技有限公司
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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 class of electroluminescent materials containing polar substituent group anthracene derivatives and its preparation method and application
  • A class of electroluminescent materials containing polar substituent group anthracene derivatives and its preparation method and application
  • A class of electroluminescent materials containing polar substituent group anthracene derivatives and its preparation method and application

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preparation example Construction

[0086] 1. Preparation of anthracene derivative monomers containing polar substituent groups

[0087] Preparation of Thiophene-3-Carboxyl Chloride

[0088] In a 500mL three-necked flask, thiophene-3-carboxylic acid (12.8g, 0.1mol) was dissolved in N,N-dimethylformamide, and 20ml of thionyl chloride was added dropwise to the reaction solution, and stirred at room temperature for 12 hours Afterwards, the reaction was stopped, the reaction was quenched with water, extracted with dichloromethane and dried with anhydrous magnesium sulfate, the solution was concentrated to obtain a khaki solid, which was purified by silica gel column chromatography, and the mixed solvent of petroleum ether / dichloromethane (3 / 1, v / v) was used as the eluent to obtain a white 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 equation of the preparation process is as follows:

[0089]

[009...

Embodiment 1

[0121] The preparation of embodiment 1 compound Z1

[0122] Under argon atmosphere, in a 100mL three-necked flask, add compound M4-1 (2.94g, 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 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 (2 / 1, v / v) as the eluent to obtain a green solid. 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:

[0123]

[0124] The thermogravimetric analysis (TGA) curve of compound Z1 is as follows figure 1shown. It can be seen from the figure that when the heat...

Embodiment 2

[0125] Embodiment 2: the synthesis of compound Z2

[0126] Under argon atmosphere, in a 100mL three-necked flask, add compound M4-1 (2.94g, 2.4mol), N-[1,1-biphenyl]-4-yl-9,9-dimethyl-9H- Fluorene-3-amine (1.81 g, 5.0 mmol), sodium tert-butylate (1.84 g, 19.2 mmol), palladium acetate (27 mg, 0.12 mmol) and 50 ml 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. 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:

[0127]

[0128] The fluorescence emission spectrum of compound Z2 in the thin film state is as follows figure 2 s...

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Abstract

The invention belongs to the technical field of organic optoelectronics, and discloses a class of electroluminescence materials containing anthracene derivatives of polar substituent groups, as well as its preparation and application. The structural formula of the electroluminescent material is as follows. The present invention introduces a double-ring structure at the 9 and 10 positions of anthracene. While preserving the advantages of the anthracene unit, the planar structure is increased, making the material difficult to crystallize, which is conducive to improving the loading capacity of the material. The transport performance of flow electrons; the introduction of solubilizing groups can significantly improve the solubility of new monomers of anthracene derivatives. The electroluminescent material obtained by coupling an appropriate unit with steric hindrance to an anthracene derivative monomer can effectively avoid fluorescence quenching caused by intermolecular aggregation in a solid state to obtain efficient and stable light-emitting device performance, and at the same time The improvement of the luminous efficiency and service life of the device can be realized, and the requirement of full-color display can be met. It can be dissolved in various polar solvents, the preparation process is green and environmentally friendly, and it has great development potential and prospects in the field of organic electronic display.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a class of electroluminescent materials containing anthracene derivatives of polar substituent groups, a preparation method and application thereof. 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/06C07F9/6561C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D495/06C07F9/6561C09K2211/1092C09K2211/1029C09K2211/1007C09K2211/1011H10K85/615H10K85/626H10K85/6576H10K85/6572H10K50/11
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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