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A kind of phenazine derivative and its application in organic electroluminescence device

A technology for electroluminescent devices and derivatives, applied to its intermediates and its preparation, application in electron transport materials, and phenazine derivatives, which can solve the problems of increasing the complexity of device manufacturing processes, reducing OLED costs, disadvantages, etc. , to achieve good electronic acceptability, reduce power consumption, and reduce the effect of working voltage

Active Publication Date: 2021-05-04
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The device based on this hybrid electron transport layer improves the device efficiency, but increases the complexity of the device manufacturing process, which is not conducive to reducing the cost of OLED

Method used

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  • A kind of phenazine derivative and its application in organic electroluminescence device
  • A kind of phenazine derivative and its application in organic electroluminescence device
  • A kind of phenazine derivative and its application in organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The synthesis of embodiment 1 dibromophenazine

[0050]

[0051] Add 3.91 grams of 4-bromo-o-phenylenediamine (molecular weight 186, 0.021 mol), 3.91 grams of 4-bromo-o-benzoquinone (molecular weight 186, 0.021 mol), ethanol (40 ml) into a 250 ml three-necked flask, and stir for 3 minutes Add 0.2 gram of concentrated sulfuric acid (concentration 98%) dropwise, and react at 65°C for 4 hours. After the reaction, cool to room temperature, filter, wash with water, dry, separate by column chromatography, and rinse with ethyl acetate / petroleum ether to obtain Almost equal amounts of 2,7-dibromophenazine and 2,8-dibromophenazine totaled 5.82 g (molecular weight: 336), and the total yield was 82.4%.

Embodiment 2

[0053] Synthesis of compound shown in formula (4)

[0054]

[0055] 1000 ml three-necked flask equipped with magnetic stirring and nitrogen protection, add 6.72 g of 2,8-dibromophenazine (molecular weight 336, 0.02 mol), 7.4 g of naphthalene-2-boronic acid (molecular weight 172, 0.043 mol), tetrakis(triphenyl 2.3 g of palladium (molecular weight: 1154, 0.002 mol), 100 ml of 2M sodium carbonate aqueous solution, 100 ml of toluene, and 100 ml of ethanol. After argon replacement, the reaction was refluxed, and the reaction was monitored by thin-layer chromatography (TLC). After 3.5 hours, TLC found that the raw material bromide was completely reacted, and only the product point was present. The temperature was lowered, the organic layer was separated, evaporated to dryness, separated by column chromatography, and washed with ethyl acetate / petroleum ether to obtain 8.1 g of the compound represented by formula (4), with a molecular weight of 432 and a yield of 93.8%.

[0056] P...

Embodiment 3

[0058] Synthesis of compound shown in formula (5)

[0059] The synthesis steps are the same as in Example 2, except that naphthalene-2-boronic acid is changed to naphthalene-1-boronic acid, and other reagents remain unchanged to obtain the compound shown in formula (5).

[0060] Product MS (m / e): 432, elemental analysis (C 32 h 20 N 2 ): theoretical value C: 88.86%, H: 4.66%, N: 6.48%; measured value C: 88.88%, H: 4.67%, N: 6.45%.

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Abstract

The present invention relates to a class of phenazine derivatives, which have the structure shown in formula (1). The phenazine derivatives of the present invention are suitable as ETL materials in electroluminescent displays. The use of the material of the invention can effectively reduce the operating voltage of the organic electroluminescent device and improve the luminous efficiency of the organic electroluminescent device.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and specifically relates to a phenazine derivative, an intermediate thereof, a preparation method thereof, and an application thereof in electron transport materials. Background technique [0002] The electron transport material traditionally used in electroluminescent devices is Alq 3 , but Alq 3 The electron mobility is relatively low (about 10 -6 cm 2 / Vs). In order to improve the electron transport performance of electroluminescent devices, researchers have done a lot of exploratory research work. [0003] LG Chem reported a series of pyrene derivatives in the patent specification CN 101003508A in China, which are used as electron transport and injection materials in electroluminescent devices to improve the luminous efficiency of the devices. Cao Yong and others synthesized FFF-Blm4 (J.Am.Chem.Soc.; (Communication); 2008; 130(11); 3282-3283) as an electron transport and inject...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/46C07D401/04C07D403/10H01L51/54
CPCC07D241/46C07D401/04C07D403/10H10K85/615H10K85/622H10K85/626H10K85/654H10K85/6572
Inventor 范洪涛李银奎邵爽任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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