A kind of benzoacridine derivative, its preparation method and its application

A technology of benzoacridine and derivatives, which is applied in the field of organic electroluminescence, can solve the problems of reducing the cost of OLEDs, disadvantages, and increasing the complexity of device manufacturing processes, etc., and achieves high glass transition temperature, good thermal stability, and good The effect of receiving electrons

Active Publication Date: 2017-11-17
GUAN ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Devices based on this hybrid electron transport layer have improved efficiency and lifetime, 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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  • A kind of benzoacridine derivative, its preparation method and its application
  • A kind of benzoacridine derivative, its preparation method and its application
  • A kind of benzoacridine derivative, its preparation method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]The synthesis of the parent 9-bromo-7-(4-bromophenyl)benzo[c]acridine (reference: Org.Biomol.Chem., 2010, 8, 326-330), the reaction route is as follows:

[0041]

[0042] N-(4-bromophenyl)-1-naphthylamine 23.8g (molecular weight 297, 0.08mol), 4-bromobenzoic acid 16g (molecular weight 200, 0.08mol), ZnCl 2 Use 16.1g (molecular weight: 134, 0.12mol) and heat in a sand bath for 5 hours while stirring at a temperature of 240-260°C. Cool, dissolve, mix with silica gel, and separate by column (eluent: dichloromethane / ethyl acetate=20:1) to obtain 18.81 g of product with a yield of 51% and a molecular weight of 463.

Embodiment 2

[0044] Synthesis of parent 9-bromo-7-(4-bromopyridin-2-yl)benzo[c]acridine

[0045] The synthesis steps are the same as the previous 1, except that benzoic acid is changed into 4-bromopyridine-2-carboxylic acid, other reagents and reaction conditions are unchanged, the reaction is completed, and column chromatography is separated to obtain the target parent 9-bromo-7-(4-bromo pyridin-2-yl)benzo[c]acridine. The reaction pathway is as follows:

[0046]

Embodiment 3

[0048] Synthesis of parent 9-bromo-7-(quinolin-2-yl)benzo[b]acridine

[0049] The synthesis steps are the same as the previous 1, except that benzoic acid is changed into quinoline-2-carboxylic acid, other reagents and reaction conditions are unchanged, the reaction is completed, and column chromatography is separated to obtain the target parent 9-bromo-7-(quinoline-2- base) benzo[b]acridine. The reaction pathway is as follows:

[0050]

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Abstract

The present invention relates to a benzoacridine derivative, which has a structure shown in formula (1), wherein: R1 and R2 are connected to form an aromatic ring fused with acridine to form a structure shown in formula (2), further, the Said R3 and R4 are connected to form an aromatic ring fused with acridine into a structure shown in formula (3). When the electroluminescence device adopts the material of the invention to prepare the electron transport layer, the turn-on voltage of the device can be reduced, the luminous efficiency of the device can be improved, and the service life of the device can be increased.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and specifically relates to a benzoacridine derivative, 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 10-6cm2 / Vs). In order to improve the electron transport performance of electroluminescent devices, researchers have done a lot of exploratory research work. LG Chem reported a series of pyrene derivatives in Chinese patent specifications, which are used as electron transport and injection materials in electroluminescent devices to improve the luminous efficiency of the devices (publication number CN 101003508A). 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D401/14C07D221/18C07D401/10H01L51/54
CPCC07D221/18C07D401/04C07D401/10C07D401/14H10K85/622H10K85/615H10K85/626H10K85/654H10K85/6572
Inventor 范洪涛李银奎汤金明任雪艳
Owner GUAN ETERNAL MATERIAL TECH
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