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Fluorene derivative and organic electroluminescent device thereof

A technology of electroluminescent devices and fluorene derivatives, which is applied in the field of fluorene derivatives and organic electroluminescent devices, can solve the problems of reduced luminous efficiency of devices, reduced probability of exciton recombination, and unstable light color of devices. Achieve good luminous efficiency and life performance, reduce energy accumulation, and improve light color stability

Active Publication Date: 2019-02-15
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Generally speaking, the direction of OLED in the future is to develop high-efficiency, high-brightness, long-life, low-cost white light devices and full-color display devices, but the industrialization process of this technology still faces many key problems. Among them, in general OLED devices In most OLED transport materials, holes have better transport properties than electrons, resulting in more holes than electrons in the light-emitting layer, resulting in a reduction in the recombination probability of excitons and a decrease in the luminous efficiency of the device.
In addition, since the amount of hole transport in the light-emitting layer is more than that of electrons, the holes will continue to transport to the cathode side, causing the shift of the light-emitting area, resulting in unstable light color of the device, local energy accumulation, and material deterioration, which eventually leads to The efficiency roll-off of the device is serious, and the life is shortened seriously

Method used

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  • Fluorene derivative and organic electroluminescent device thereof
  • Fluorene derivative and organic electroluminescent device thereof
  • Fluorene derivative and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] [Example 1] Synthesis of Compound A-1

[0091]

[0092] Step1: Under the protection of nitrogen, the compound 2-bromo-9-fluorenone (2.59g, 10mmol) was added to the reactor and completely dissolved in 50mL DMF solution, stirred at room temperature, and then malononitrile (0.79g, 12mmol) was added, Stir the reaction at room temperature for 1 h, add deionized water to stop the reaction after the reaction, stir for 10 min, filter to obtain the precipitate, dilute the precipitate with ethyl acetate, anhydrous MgSO 4 Dry, filter, concentrate, and go through silica gel column chromatography to obtain intermediate A-1-1 (1.66 g, 54%).

[0093] Step2: Under nitrogen, add intermediate A-1-1 (3.07g, 10mmol), triphenylene-2-boronic acid (2.72g, 10mmol), tetrakistriphenylphosphine palladium (0.12g, 0.1 mmol), sodium carbonate (4.14g, 30mmol), toluene 100mL, ethanol 20mL and distilled water 20mL, stirred and refluxed for 3h. After the reaction was finished, stop the reaction wit...

Embodiment 2

[0094] [Example 2] Synthesis of Compound A-3

[0095]

[0096] Step1: Add hexafluorobenzonitrile (1.93g, 10mmol), ethyl cyanoacetate (1.11g, 10mmol), potassium carbonate (1.67g, 12.1mmol), 30mL of DMF into the reactor, stir the reaction at room temperature for 48h, then add Distilled water and acetic acid terminated the reaction, extracted with dichloromethane and concentrated to obtain intermediate A-3-1 (2.83 g, 99%).

[0097] Step2: Add intermediate A-3-1 (2.86g, 10mmol), 50% acetic acid (4.10mL) and sulfuric acid (0.2mL) to the reactor, stir after reflux for 16h, cool the mixture to room temperature, add dropwise 10mL of cold distilled water After the reaction was terminated, the mixture was stirred for 0.5 h, and the reaction mixture was extracted with distilled water and chloroform, and then concentrated to obtain intermediate A-3-2 (2.06 g, 96%).

[0098] Step3: Under nitrogen protection, add 2-bromo-9-fluorenone (2.59g, 10mmol), intermediate A-3-2 (2.57g, 12mmol) a...

Embodiment 3

[0100] [Example 3] Synthesis of Compound A-19

[0101] Compound A-19 (5.63 g, 78%) was obtained according to the synthesis method of compound A-3.

[0102]

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PUM

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Abstract

The invention provides a fluorine derivative and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. The fluorine derivative is formedby connecting a strong electron-withdrawing group on one side of a fluorene main structure through double bonds and connecting a triphenylene structure on the other side, has good electron transport ability and hole transport ability, is capable of effectively improving the injection rates and exciton recombination rates of current carriers in light emitting layers, is good in thermal stability, good in film formation property, simple to synthesize and easy to operate, can be applied in an organic electroluminescent device to serve as a light-emitting layer main body and / or a hole blocking layer, and is capable of effectively solving the problem that organic light emitting devices are unbalanced in current carrier transport, low in luminous efficiency, short in service life and unstable incolor of light; and the organic electroluminescent device has the advantages of being low in driving voltage, high in luminous efficiency and long in service life.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a fluorene derivative and an organic electroluminescence device thereof. Background technique [0002] Organic electroluminescent device (OLED), as a new type of flat panel display, has the characteristics of self-illumination, wide viewing angle, full curing, full color, fast response, high brightness, low driving voltage, thin thickness, light weight, and In recent years, OLED has been more and more used in the display market due to the characteristics of making large-size and curved panels, and has become the most potential panel display technology at present. [0003] The structure of a classic organic electroluminescent device is a sandwich structure, generally including a cathode, an anode and an organic layer between them. The organic layer can roughly include one or more of a hole injection layer, a hole transport layer, a light emitting layer, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/34C07C255/35C07C255/50C07C255/51C07D213/57C07D213/61C07D213/84C07D239/26C07D239/30C07D251/20C07D251/24C07D307/91C07D401/10C07D403/10C09K11/06H01L51/54
CPCC09K11/06C07C255/34C07C255/35C07C255/50C07C255/51C07D213/57C07D213/61C07D213/84C07D239/26C07D239/30C07D251/20C07D251/24C07D307/91C07D401/10C07D403/10C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C07C2603/18H10K85/615H10K85/622H10K85/626H10K85/654
Inventor 董秀芹蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD
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