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

A technology of benzophenazine and its derivatives, which is applied in the field of organic electroluminescence, can solve the problems of increasing the complexity of device manufacturing process, reducing the cost of OLED, and unfavorable problems, so as to achieve good electron acceptance ability, improve luminous efficiency, and reduce operating voltage Effect

Active Publication Date: 2020-01-14
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 benzophenazine derivative and its application in organic electroluminescence device
  • A kind of benzophenazine derivative and its application in organic electroluminescence device
  • A kind of benzophenazine derivative and its application in organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The synthesis of embodiment 1 dibromobenzophenazine intermediate

[0048] 1,5,9-Dibromobenzo[a]phenazine and 5,10-dibromobenzo[a]phenazine

[0049]

[0050] Add 3.91 grams of 4-bromo-o-phenylenediamine (molecular weight 186, 0.021mol), 4.96 grams of 4-bromonaphthalene-1,2-dione (molecular weight 236, 0.021mol), ethanol (40 milliliters) in the 250ml there-necked flask, Under the condition of stirring, 0.2 g of concentrated sulfuric acid was added dropwise within 3 minutes, and reacted at 65°C for 4 hours. After the reaction was completed, it was cooled to room temperature, filtered, washed with water, dried, separated by column chromatography, and rinsed with ethyl acetate / petroleum ether to obtain Almost equal amounts of 5,9-dibromobenzo[a]phenazine and 5,10-dibromobenzo[a]phenazine totaled 6.86 g (molecular weight 386), with a total yield of 84.6%.

[0051] 2,3,9-Dibromobenzo[a]phenazine and 3,10-dibromobenzo[a]phenazine

[0052] The synthesis process is the same ...

Embodiment 2

[0054] Synthesis of compound shown in formula (7)

[0055]

[0056] 1000ml three-necked flask, equipped with magnetic stirring, nitrogen protection, add 7.72g of 5,9-dibromobenzo[a]phenazine (molecular weight 386, 0.02mol), naphthalene-2-boronic acid 7.4g (molecular weight 172, 0.043mol) , tetrakis ((triphenylphosphine) palladium 2.3g (molecular weight 1154, 0.002mol), 2M sodium carbonate aqueous solution 100ml, toluene 100ml, ethanol 100ml. After argon replacement, reflux, monitor with thin layer chromatography (TLC) method Reaction, after 4 hours TLC finds that raw material bromide reaction is complete, only product point.Cool down, separate organic layer, evaporate to dryness, column chromatography, ethyl acetate / sherwood oil washing, obtain the compound shown in 8.1g formula (7) , molecular weight 482, yield 86.7%.

[0057] Product MS (m / e): 482, elemental analysis (C 36 h 22 N 2 ): theoretical value C: 89.60%, H: 4.60%, N: 5.81%; measured value C: 89.54%, H: 4.62%,...

Embodiment 3

[0059] Synthesis of compound shown in formula (8)

[0060] 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 are kept unchanged to obtain the compound represented by formula (8).

[0061] Product MS (m / e): 482, elemental analysis (C 36 h 22 N 2 ): theoretical value C: 89.60%, H: 4.60%, N: 5.81%; measured value C: 89.56%, H: 4.58%, N: 5.86%.

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Abstract

The present invention relates to a class of benzophenazine derivatives, which have the structures shown in formulas (1) and (2). The benzophenazine 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 benzophenazine 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 i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/46C07D241/38H01L51/54
CPCH10K85/6576
Inventor 范洪涛李银奎邵爽任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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