Polycyclic aromatic hydrocarbon derivatives containing quinoxaline groups and application thereof

A technology of quinoxaline group and fused ring aromatic hydrocarbons, which is applied in the direction of electrical components, circuits, organic chemistry, etc., can solve the problems of increasing the complexity of the device manufacturing process, reducing the cost of OLEDs, disadvantages, etc., and achieve good electronic acceptance, good The effect of electromobility

Active Publication Date: 2020-05-22
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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  • Polycyclic aromatic hydrocarbon derivatives containing quinoxaline groups and application thereof
  • Polycyclic aromatic hydrocarbon derivatives containing quinoxaline groups and application thereof
  • Polycyclic aromatic hydrocarbon derivatives containing quinoxaline groups and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] The synthesis of various quinoxaline boronic acid derivative intermediates of embodiment 1

[0074] Synthesis of 1,6-bromo-2,3-diphenylquinoxaline

[0075]

[0076] Add 3.91 grams of 4-bromo-o-phenylenediamine (molecular weight 186, 0.021 mol), 4.41 grams of diphenyl ketone (molecular weight 210, 0.021 mol), ethanol (40 ml), and stir for 3 minutes in a 250 ml three-necked flask. Add 0.2 g of concentrated sulfuric acid dropwise, and react at 65°C for 4 hours. After the reaction, cool to room temperature, filter, and wash with 50 ml of ethanol and 50 ml of petroleum ether in turn to obtain the intermediate compound 6-bromo-2,3-diphenyl 6.66 grams of quinoxaline (molecular weight: 360), yield 88.1%.

[0077] Synthesis of 2,7-bromo-1,2,3,4-tetrahydrophenazine

[0078]

[0079] The reaction steps are the same as the synthesis of 6-bromo-2,3-diphenylquinoxaline, except that diphenylethanedione is replaced by 1,2-cyclohexanedione to obtain the intermediate 7-bromo-1,2 ...

Embodiment 2

[0093] Synthesis of compound shown in formula (12)

[0094]

[0095] 1000ml three-neck flask equipped with magnetic stirring and nitrogen protection, add 4.72g of 6-bromo-2,3-dimethylquinoxaline (molecular weight 236, 0.02mol), 9,10-di(naphthalene-2-yl)anthracene -2-boronic acid 11.0g (molecular weight 474, 0.022mol), tetrakis ((triphenylphosphine) palladium 1.16g (molecular weight 1154, 0.001mol), 2M sodium carbonate aqueous solution 80ml, toluene 80ml, ethanol 80ml. Argon displacement Afterwards, reflux, monitor reaction with thin-layer chromatography (TLC) method, after 4 hours, TLC finds that raw material bromide reaction is complete, only product point.Cool down to 25 ℃, separate organic layer, evaporate to dryness, column chromatographic separation, ethyl acetate / petroleum ether to obtain 11.7 g of the compound represented by formula (12), with a molecular weight of 586 and a yield of 87.4%.

[0096] Product MS (m / e): 586, elemental analysis (C 44 h 30 N 2 ): the...

Embodiment 3

[0098] Synthesis of compound shown in formula (13)

[0099] The synthesis steps are the same as in Example 2, except that 6-bromo-2,3-dimethylquinoxaline is changed to 7-bromo-1,2,3,4-tetrahydrophenazine, and other reagents remain unchanged to obtain the formula Compound shown in (13).

[0100] Product MS (m / e): 612, elemental analysis (C 46 h 32 N 2 ): theoretical value C: 90.16%, H: 5.26%, N: 4.57%; measured value C: 90.12%, H: 5.22%, N: 4.66%.

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Abstract

The invention relates to polycyclic aromatic hydrocarbon derivatives containing quinoxaline groups. The compounds have structures as shown in a formula (1) which is described in the specification. Thepolycyclic aromatic hydrocarbon derivatives containing the quinoxaline groups are applicable as ETL materials in electroluminescent displays. By using the polycyclic aromatic hydrocarbon derivatives,the working voltage of organic light-emitting devices can be effectively reduced, and the light-emitting efficiency of the organic light-emitting devices can be improved.

Description

[0001] This application is a divisional application of "the application date is September 30, 2015, the application number is: 201510641431.0, and the invention name is a quinoxaline-based fused-ring aromatic derivative and its application". technical field [0002] The invention belongs to the field of organic electroluminescence, and in particular relates to a condensed ring aromatic hydrocarbon derivative containing a quinoxaline group and its application 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 10-6cm 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 reported a series of pyrene derivatives in CN101003508A, which are used as electron transport and injection materials in electrolumines...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/42C07D241/44C07D241/38H01L51/54
CPCC07D241/38C07D241/42C07D241/44H10K85/623H10K85/622H10K85/626H10K85/6572
Inventor 范洪涛李银奎邵爽任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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