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Fullerene derivative, application thereof and OLED device containing fullerene derivative

A technology of fullerene derivatives and devices, which is applied in the preparation of electric solid devices, semiconductor devices, organic compounds, etc. There are many problems such as the urgent need to develop hybrid materials to achieve the effects of high structural stability and thermal stability, improved binding rate, and good electron receiving ability.

Active Publication Date: 2020-02-21
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, there are few researches on OLED devices, and there are few available hole transport layer doping materials, and new hole transport layer doping materials still need to be developed urgently

Method used

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  • Fullerene derivative, application thereof and OLED device containing fullerene derivative
  • Fullerene derivative, application thereof and OLED device containing fullerene derivative
  • Fullerene derivative, application thereof and OLED device containing fullerene derivative

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0061] The preparation of compound 1-1, its synthetic route is as follows:

[0062]

[0063] Concrete synthetic steps are as follows:

[0064] (1) Anhydrous tetrahydrofuran (500 mL) was added to a 1000 mL three-necked flask, sodium hydride (28.8 g, 1.2 mol) was added under ice-bath conditions, and malononitrile (66.1 g, 1.0 mol) was slowly added dropwise under nitrogen protection,

[0065] After the dropwise addition, stir in an ice bath for 1 hour, then add acetyl chloride (78.5 g, 1.0 mol) dropwise, after the dropwise addition, stir at room temperature for 4 hours, slowly add methanol (10 mL), stir for 10 minutes, then add water ( ), extracted with ethyl acetate (300mL×2), combined the organic phases, washed once with water (200mL), washed once with saturated brine (100mL), dried over sodium sulfate, filtered, and spin-dried to obtain the crude product as a yellow solid (98.5g ), flash column purification (eluent: petroleum ether / ethyl acetate = 10:1-4:1, eluted in diffe...

preparation example 2

[0071] Compound 1-2 The preparation of the specific synthesis steps are as follows:

[0072] (1) Add compound B (13.8g, 0.050mol) into a 1000mL three-necked flask, protect it under nitrogen, inject re-distilled pyridine (150mL), stir and dissolve, add sodium methoxide (4.05g, 0.075mol), and then heat up to 80°C; After the reaction system was stirred at 80°C for 10 minutes, a solution of o-dichlorobenzene (500mL) in fullerene C60 (12.5g, 0.017mol) was added dropwise, and after the addition was completed, the reaction was continued at 80°C for 24 hours; After cooling to room temperature, the reaction solution was poured into methanol and left to stand for 4 hours before filtering, and the filter cake was redispersed and then subjected to column separation (toluene / petroleum ether=1:1) to obtain 6.7g of crude product; the resulting crude product was dissolved in Chloroform, after filtering through a 0.20 μm polytetrafluoroethylene (PTFE) filter membrane, a small amount of multi...

preparation example 3

[0076] The preparation of compound 16-1, its synthetic route is as follows:

[0077]

[0078] Concrete synthetic steps are as follows:

[0079] (1) Add anhydrous tetrahydrofuran (500mL) into a 1000mL three-necked flask, add sodium hydride (14.4g, 0.60mol) under ice bath conditions, and slowly add 4-cyanomethyl-2,3,5,6 -Tetrafluorobenzonitrile (compound C, 107.1g, 0.50mol), after the dropwise addition, stir in an ice bath for 1 hour, then add acetyl chloride (39.25g, 0.5mol) dropwise, after the dropwise addition, stir at room temperature for 4 hours, Slowly add methanol (10mL), stir for 10 minutes, add water (500mL), extract with ethyl acetate (300mL×2), combine the organic phases, wash once with water (200mL), wash once with saturated brine (100mL), sulfuric acid Sodium-dried, filtered, and spin-dried to obtain the crude product as a yellow solid (123.7 g), which was purified by flash column (eluent: petroleum ether / ethyl acetate=10:1-4:1, eluted in different proportions), ...

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Abstract

The invention provides a fullerene derivative, application thereof and an OLED device containing the fullerene derivative. The fullerene derivative has a structure shown as a formula I, and is obtained by carrying out addition reaction on an electron withdrawing group and fullerene. The fullerene derivative provided by the invention can be used as a hole transport layer doping material of the OLEDdevice; the fullerene derivative has a low lowest unoccupied molecular orbital energy level, and is beneficial to receiving electrons on the highest occupied molecular orbital energy level of a holetransport material, so that holes are formed, the hole concentration is improved, the combination rate of the holes and the electrons is improved, the working voltage of the OLED device is reduced, and the luminous efficiency is improved; moreover, the fullerene derivative provided by the invention has relatively high structural stability, and is beneficial to prolonging the service life of the OLED device.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a fullerene derivative, its application and an OLED device containing it. Background technique [0002] In 1987, Tang et al. from Kodak Company of the United States successfully developed low-voltage, high-brightness organic light-emitting diodes with organic small molecule materials. It has attracted wide attention due to its many advantages, and has great application prospects in the fields of display and lighting. [0003] It is generally believed that the light-emitting mechanism of OLED is: driven by an external voltage, carriers (electrons and holes) are respectively injected from two electrodes, meet in the organic layer, form excitons, release and transfer energy to organic light-emitting materials, and make organic The luminescent material transitions from the ground state to the excited state, and the excited state is deactivated by ...

Claims

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Application Information

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IPC IPC(8): C07C255/31C07C253/30C07C255/51C07D213/61H01L51/50H01L51/54
CPCC07C255/31C07C255/51C07D213/61C07B2200/11C07C2604/00H10K85/215H10K85/654H10K50/155Y02E10/549
Inventor 丁欢达魏定纬谢坤山陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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