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Benzacridine derivative as well as preparation method and application thereof

A technology of benzoacridine and derivatives, 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., and achieves good electron acceptance, high Tg, and high glass transition The effect of temperature

Active Publication Date: 2015-06-10
BEIJING ETERNAL MATERIAL TECH
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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 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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  • Benzacridine derivative as well as preparation method and application thereof
  • Benzacridine derivative as well as preparation method and application thereof
  • Benzacridine derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of the parent 2-bromo-12-(4-bromophenyl)benzo[b]acridine and 10-bromo-12-(4-bromophenyl)benzo[a]acridine (ref: Org. Biomol.Chem., 2010,8,326-330), the reaction pathway is as follows:

[0037]

[0038] N-(4-bromophenyl)-2-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). Under the protection of nitrogen, stir and heat in a sand bath for 5 hours at a temperature of 240-260°C. Cool, dissolve, mix with silica gel, separate by column (eluent: dichloromethane / ethyl acetate=20:1), and isolate 10.5g of 2-bromo-12-(4-bromophenyl)benzo[b] Acridine, yield 28.3%, isolated 9.3 g of 10-bromo-12-(4-bromophenyl)benzo[a]acridine, yield 25.1%, molecular weight 463.

Embodiment 2

[0040] Synthesis of parent 2-bromo-12-(4-bromopyridin-2-yl)benzo[b]acridine and 10-bromo-12-(4-bromopyridin-2-yl)benzo[a]acridine

[0041] The synthesis steps are the same as the previous 1, except that benzoic acid is changed to 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 2-bromo-12-(4-bromo pyridin-2-yl)benzo[b]acridine and 10-bromo-12-(4-bromopyridin-2-yl)benzo[a]acridine. The reaction pathway is as follows:

[0042]

Embodiment 3

[0044] Synthesis of parent 2-bromo-12-(quinolin-2-yl)benzo[b]acridine and 10-bromo-12-(quinolin-2-yl)benzo[a]acridine

[0045] The synthesis steps are the same as the previous 1, except that benzoic acid is changed to 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 2-bromo-12-(quinoline-2- yl)benzo[b]acridine and 10-bromo-12-(quinolin-2-yl)benzo[a]acridine. The reaction pathway is as follows:

[0046]

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Abstract

The invention relates to a benzacridine derivative. The structure of the benzacridine derivative is as shown in a formula (1). In the formula, R2 is bonded with R1 or R3 to form an aromatic ring. The aromatic ring is condensed with acridine to form a structure as shown in a formula (2) or (3). When the material provided by the invention is used for preparing an electron transfer layer of an electroluminescent device, the turn-on voltage of the device can be reduced, the luminous efficiency of the device is improved, and the service life of the device is prolonged.

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 Alq3, but the electron mobility of Alq3 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 (w...

Claims

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Application Information

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