Benzidine derivative and organic light-emitting diode thereof

A technology of electroluminescent devices and derivatives, applied in the direction of electric solid state devices, electrical components, organic chemistry, etc., can solve the problems of unsatisfactory luminescence characteristics, improve the glass transition temperature and thermal stability, and achieve long-term use Effects of Lifetime, High Luminous Efficiency and Luminous Brightness

Inactive Publication Date: 2018-11-16
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the hole transport layer, the traditionally used materials usually cannot provide satisfactory luminescent properties. Therefore, it is still necessary to design new hole transport materials with better performance to improve the performance of organic electroluminescent devices.

Method used

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  • Benzidine derivative and organic light-emitting diode thereof
  • Benzidine derivative and organic light-emitting diode thereof
  • Benzidine derivative and organic light-emitting diode thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0080] Preparation of Compound Sub I-1:

[0081]

[0082] Under argon protection, bis(4-biphenyl)amine (10g, 31mmol), 4-bromo-4-iodobiphenyl (11.1g, 31mmol), sodium tert-butoxide (3g, 31mmol), Bis(triphenylphosphine)palladium(II) dichloride (0.5g, 0.71mmol) and toluene (500ml) were reacted at 130°C for 24 hours. After cooling, water (1000ml) was added, the mixture was filtered, the filtrate was extracted with toluene, and the organic phase was dried over anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the resulting crude product was column-purified, recrystallized from toluene, filtered, and dried to obtain an intermediate Sub I-1 (10.5 g, 61%).

Embodiment 1

[0084] Preparation of Compound Sub II-1:

[0085]

[0086] Under argon protection, 3-methoxy-2-naphthaleneboronic acid (21.2g, 105mmol), 1-bromo-3-fluoro-4-iodobenzene (30.0g, 100mmol), Pd(PPh 3 ) 4 (2.31g, 2mmol), toluene (300ml), aqueous sodium carbonate solution (2M, 150ml), and stirred at reflux for 8 hours. After the above reaction solution was cooled to room temperature, it was extracted with toluene, the organic phases were combined, and the organic phase was washed with saturated brine. After the organic phase was dried and concentrated, column chromatography was performed using silica gel as a stationary phase to obtain compound A1 (23.2 g, 70%).

[0087] Add compound A1 (23.2g, 70mmol) and dry dichloromethane (200ml) to the flask successively, and cool the reaction system to 0°C. Join BBr 3 (22.0g, 88mmol), then stirred at room temperature for 24 hours. After the reaction, the solution was cooled to -78°C, carefully deactivated with methanol, and then deactiv...

Embodiment 2

[0102] Preparation of Compound Sub III-2:

[0103]

[0104] Under argon protection, 3-bromo-9-ethylcarbazole (27.4 g, 100 mmol) was added to the flask, poured into an appropriate amount of anhydrous THF to dissolve, cooled to -78 ° C, and added dropwise n-butyllithium ( 7.7g, 120mmol), heat preservation reaction for 0.5 hours, quickly drop triisopropyl borate (28.2g, 150mmol), slowly warm up to room temperature, and react for 30min. After the reaction was completed, the reaction solution was poured into dilute hydrochloric acid aqueous solution, and a solid substance was precipitated and filtered, and the crude product was passed through a silica gel column to obtain compound C1 (23.8 g, 75%).

[0105] Under argon protection, compound C1 (40.7g, 128.1mmol), 2-nitroiodobenzene (26.6g, 106.8mmol), Na 2 CO 3 (34.0g, 320.4mmol), tetrakistriphenylphosphine palladium (6.17g, 5.3mmol), toluene (640ml) and ethanol (160ml), the reaction mixture was stirred at 90°C for 3 hours. Af...

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Abstract

The invention discloses a benzidine derivative and an organic light-emitting diode thereof and relates to the technical field of organic optoelectronic materials. Aromatic amine nitrogen atoms on thebenzidine derivative disclosed by the invention contain lone pair electrons and show good electropositivity; the benzidine derivative disclosed by the invention has a larger conjugation system, thereby having higher hole mobility and showing better hole transport performance. In addition, a substituted group with large volume is also introduced into the benzidine derivative disclosed by the invention, so that the glass temperature and thermal stability of a material are effectively improved, and the material film formation is facilitated. The organic light-emitting diode comprises an anode, acathode and one or more organic matter layers; the organic matter layers are positioned between the anode and the cathode; at least one of the organic matter layers contains the benzidine derivative disclosed by the invention. The organic light-emitting diode disclosed by the invention has lower drive voltage, higher luminous efficiency and luminous brightness and longer service life.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a benzidine derivative and an organic electroluminescent device. Background technique [0002] Organic optoelectronic materials are organic materials with photon and electron generation, conversion and transport properties. Currently, organic photoelectric materials have been applied to organic electroluminescent devices (Organic Light-Emitting Diode, OLED). OLED refers to a device in which organic photoelectric materials emit light under the action of current or electric field, which can directly convert electrical energy into light energy. In recent years, OLED as a new generation of flat panel display and solid-state lighting technology is receiving more and more attention. Compared with liquid crystal display technology, OLED is more and more used in the field of display and lighting due to its low power consumption, active light emission, fast respo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/94C07D209/96C07D401/12C07D403/12C07D405/12C07D409/12C07D471/04C07D487/04C07D491/048C07D495/04H01L51/54
CPCC07D209/94C07D209/96C07D401/12C07D403/12C07D405/12C07D409/12C07D471/04C07D487/04C07D491/048C07D495/04H10K85/631H10K85/636H10K85/633H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/6572
Inventor 周雯庭蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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