Polycyclic aromatic hydrocarbon derivative comprising quinoxaline group and application thereof

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

Active Publication Date: 2017-04-05
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 derivative comprising quinoxaline group and application thereof
  • Polycyclic aromatic hydrocarbon derivative comprising quinoxaline group and application thereof
  • Polycyclic aromatic hydrocarbon derivative comprising quinoxaline group and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] The synthesis of various quinoxaline boronic acid derivative intermediates of embodiment 1

[0072] Synthesis of 1,6-bromo-2,3-diphenylquinoxaline

[0073]

[0074] 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%.

[0075] Synthesis of 2,7-bromo-1,2,3,4-tetrahydrophenazine

[0076]

[0077] 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

[0091] Synthesis of compound shown in formula (12)

[0092]

[0093] 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%.

[0094] Product MS (m / e): 586, elemental analysis (C 44 h 30 N 2 ): the...

Embodiment 3

[0096] Synthesis of compound shown in formula (13)

[0097] 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).

[0098] 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 a polycyclic aromatic hydrocarbon derivative comprising a quinoxaline group. The compound has the structure represented as the formula (I). The polycyclic aromatic hydrocarbon derivative is suitable for being used as an ETL material in electroluminescence displayers. The compound can effectively reduce operating voltage of an organic light-emitting device, and can improve the luminous efficiency of the organic light-emitting device.

Description

technical field [0001] 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 [0002] 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. [0003] LG Chem reported a series of pyrene derivatives in CN 101003508A, 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 injection layer material (with Ba / Al and Al alon...

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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