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Phenazine group substituted polycyclic aromatic hydrocarbon derivative and application thereof

A technology of fused-ring aromatic hydrocarbons and fused-ring aromatic hydrocarbons, which is applied in the field of organic electroluminescence, can solve the problems of increasing the complexity of the device manufacturing process, reducing the cost of OLEDs, disadvantages, etc., achieving good electron acceptance capabilities, improving luminous efficiency, and reducing work The effect of voltage

Active Publication Date: 2020-06-19
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Devices based on this hybrid electron transport layer improve device efficiency, but increase the complexity of the device manufacturing process, which is not conducive to reducing the cost of OLEDs

Method used

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  • Phenazine group substituted polycyclic aromatic hydrocarbon derivative and application thereof
  • Phenazine group substituted polycyclic aromatic hydrocarbon derivative and application thereof
  • Phenazine group substituted polycyclic aromatic hydrocarbon derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 12

[0048] The synthesis of embodiment 12-bromophenazine

[0049]

[0050]Add 3.91 grams of 4-bromo-o-phenylenediamine (molecular weight 186, 0.021mol), 2.27 grams of o-benzoquinone (molecular weight 108, 0.021mol), and ethanol (40 ml) into a 250ml three-necked flask. 0.2 gram of concentrated sulfuric acid was reacted at 65°C for 4 hours. After the reaction was over, it was cooled to room temperature, filtered, and washed with ethanol and petroleum ether successively to obtain 5.02 grams of intermediate compound 2-bromophenazine (molecular weight 258), with a yield of 92.6 %.

Embodiment 2

[0052] Compounds are synthesized according to the following reactions

[0053]

[0054] 1000 ml three-necked flask equipped with magnetic stirring and nitrogen protection, add 5.16 g of 2-bromophenazine (molecular weight 258, 0.02 mol), 11.0 g of 9,10-bis(naphthalene-2-yl)anthracene-2-boronic acid (molecular weight 474 , 0.022mol), tetrakis ((triphenylphosphine) palladium 1.16g (molecular weight 1154, 0.001mol), 80ml of aqueous sodium carbonate solution of 2M, toluene 80ml, ethanol 80ml, after argon replacement, reflux, use thin-layer chromatography ( TLC) method monitoring reaction, after 4.5 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 9.94g chemical formula and generate The compound shown in the compound has a molecular weight of 608 and a yield of 81.7%.

[0055] Product MS (m / e): 608, elemental analysis (C 4...

Embodiment 3

[0057] Synthesis of compound shown in formula (5)

[0058] The synthesis steps are the same as in Example 2, except that 9,10-bis(naphthalene-2-yl)anthracene-2-boronic acid is changed to 7-(naphthalene-2-yl)triphenylene-2-boronic acid, and other reagents remain unchanged. The compound represented by formula (5) was obtained.

[0059] Product MS (m / e): 582, elemental analysis (C 44 h 26 N 2 ): theoretical value C: 90.69%, H: 4.50%, N: 4.81%; measured value C: 90.64%, H: 4.52%, N: 4.84%.

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Abstract

The invention relates to a phenazine group substituted polycyclic aromatic hydrocarbon derivative. The compound has a structure shown as a formula (1). The phenazine group substituted polycyclic aromatic hydrocarbon derivative is suitable for being used as an ETL material in an electroluminescent display. With application of the material, the turn-on voltage of the device is reduced, the luminousefficiency of the device is improved and the service life of the device is prolonged. .

Description

[0001] This application is the application number 201510642570.5, the application date: 2015.09.30, the title of the invention: a divisional application of a fused ring aromatic derivative substituted by a phenazine group and its application. technical field [0002] The invention belongs to the field of organic electroluminescence, and in particular relates to a fused-ring aromatic hydrocarbon derivative substituted by a phenazine group, an intermediate thereof, a preparation method thereof, and an application thereof in electron transport materials. Background technique [0003] 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. [0004] LG Chem has reported a series of pyrene derivatives in Chinese patent CN 10100...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/46H01L51/50H01L51/54
CPCC07D241/46H10K85/6572
Inventor 范洪涛李银奎邵爽任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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