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A class of electroluminescent compound and its preparation method and application

A compound and luminescent technology, applied in the direction of silicon organic compounds, chemical instruments and methods, luminescent materials, etc., can solve the problems of easy crystallization of organic materials, affecting life and efficiency, and short service life, so as to facilitate normal use, The effect of reducing preparation cost and low price

Active Publication Date: 2020-06-05
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

[0003] After decades of rapid development, OLED flat panel display technology is becoming mature and has occupied a place in the field of flat panel display, but the current OLED devices are restricted from wider application due to factors such as low efficiency and short service life, especially in Large screen display field
In addition, when the device is operated with an applied voltage, it will generate Joule heat, which makes the organic material easy to crystallize, which affects its life and efficiency to a certain extent.

Method used

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  • A class of electroluminescent compound and its preparation method and application
  • A class of electroluminescent compound and its preparation method and application
  • A class of electroluminescent compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0045] monomer preparation

[0046] Preparation of ethyl 3-bromopyrazine-2-carboxylic acid

[0047] In a 500mL three-necked flask, 3-bromopyrazine-2-carboxylic acid (20.3g, 0.1mol) was dissolved in 200ml of methanol, and 20ml of concentrated sulfuric acid was added dropwise to the reaction solution, and stirred at room temperature for 12 hours Afterwards, stop the reaction, quench the reaction with water, extract with dichloromethane and dry with anhydrous magnesium sulfate, obtain a yellow liquid after the solution is concentrated, purify by silica gel column chromatography, the mixed solvent of sherwood oil / dichloromethane (volume ratio 2 / 1) is the eluent, and the yield is 83%. 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:

[0048]

[0049] 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[4,5]thiophene[2,3-b]pyridine prepar...

Embodiment 1

[0065] The synthesis of embodiment 1 electroluminescence material PM1

[0066] Under argon atmosphere, in a 100mL three-necked flask, add compound P1 (1.39g, 2.4mmol), diphenylamine (0.85g, 5.0mmol), sodium tert-butyl alkoxide (1.84g, 19.2mmol), palladium acetate (27mg , 0.12mmol) and 50ml toluene. Heat and stir, when the temperature stabilizes to 85°C, add 0.24ml of tri-tert-butylphosphine toluene solution with a concentration of 1mol / 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, volume ratio) as the eluent, and finally a yellow 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:

[0067]

[0068] The differential scanning calorimetry (DSC) curve of compound PM...

Embodiment 2

[0069] The synthesis of embodiment 2 electroluminescence material PM2

[0070] Under argon atmosphere, in a 100mL three-necked flask, add compound P1 (1.39g, 2.4mmol), 9,9-diphenyl-9,10-dihydroacridine (1.67g, 5.0mmol), tert-butyl Sodium alkoxide (1.84g, 19.2mmol), palladium acetate (27mg, 0.12mmol) and 50ml of toluene. Heat and stir, when the temperature stabilizes to 85°C, add 0.24ml of tri-tert-butylphosphine toluene solution with a concentration of 1mol / 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, volume ratio) as the eluent, and finally a yellow 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:

[0071]

[0072] The thermogravimetric (TG) curve of compou...

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Abstract

The invention discloses a class of electroluminescence compound, its preparation method and application. The compound has the following structure: or the H on the ring is replaced by Ar. Obtained by C‑C coupling or C‑N coupling reaction. The prepared compound contains heteroatoms, which can improve the fluorescence quantum yield and carrier transport capacity of the luminescent material; it is not easy to crystallize under solid-state conditions; it has the advantages of high thermal decomposition temperature and strong heat resistance, and is used in luminescence Diodes, organic field effect transistors, organic solar cells, organic laser diodes.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a class of electroluminescent compounds and their preparation methods and applications. Background technique [0002] Organic light-emitting diode (OLED) displays use organic materials as light-emitting materials. The material structure is easy to modify and improve, and the selection range is wide; the driving voltage is low, only 3-12V DC voltage is required; self-illumination, no backlight is required; wide viewing angle , can be close to 180°; the response speed is fast, up to 1 μs; in addition, it has the advantages of light weight, ultra-thin, large size, flexible panel, and easy molding and processing. Due to the many advantages of OLED displays, it has attracted extensive attention from the scientific and industrial circles. Since Kodak Corporation of the United States developed OLED devices in 1987, many institutions have invested resources in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22C07F7/08C09K11/06H01L51/54
CPCC09K11/06C07D495/22C07F7/0812C09K2211/1092C09K2211/1007C09K2211/1014C09K2211/1011C09K2211/1044C09K2211/1029H10K85/636H10K85/626H10K85/657H10K85/6572H10K85/40Y02E10/549
Inventor 应磊胡黎文黄飞曹镛
Owner 东莞伏安光电科技有限公司