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A kind of * class derivative containing quinazoline group and application thereof

A quinazoline-based, quinazoline-containing technology, applied in the field of organic electroluminescence, can solve the problems of increasing the complexity of the device manufacturing process, reducing the cost of OLED, disadvantage, etc. Effect

Active Publication Date: 2020-07-21
BEIJING ETERNAL MATERIAL TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The device based on this hybrid electron transport layer improves the device efficiency, but increases the complexity of the device manufacturing process, which is not conducive to reducing the cost of OLED

Method used

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  • A kind of * class derivative containing quinazoline group and application thereof
  • A kind of * class derivative containing quinazoline group and application thereof
  • A kind of * class derivative containing quinazoline group and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1 Synthesis of various quinazoline derivative intermediates

[0054] Synthesis of 1,5-bromo-2-aminobenzylamine

[0055]

[0056] Add 5.9 g (molecular weight 196, 0.030 mol) of 2-amino-5-bromobenzonitrile to a 500 ml three-necked flask, and then add 45 ml of anhydrous tetrahydrofuran, stir to dissolve, and cool to 0°C. Under 0° C., nitrogen protection and stirring, 40 ml of borane tetrahydrofuran (concentration 1M) was slowly added to the three-necked flask. Stir at room temperature for three days. Cool to 0°C, add 20ml of absolute ethanol, and blow dry 1200ml of HCl gas. Then it was concentrated, cooled to 25°C, and 30 ml of isopropyl ether was added to precipitate the product. Then, under cooling and nitrogen protection, the solid product was added to 50 ml ammonia water, stirred, extracted with ethyl acetate, and the solvent was evaporated to obtain a solid product, which was dried to obtain 5.4 g, a molecular weight of 200, and a yield of 89.6%.

[0057] Synthes...

Embodiment 2

[0067] Synthesis of compound represented by formula (5)

[0068]

[0069] 1000ml bottle with magnetic stirring, add 6.68g 6-bromo-2-(naphthalene-2-yl)quinazoline (molecular weight 334, 0.02mol), 12-(naphthalene-2-yl) -6-Boric acid 8.76g (molecular weight 398, 0.022mol), tetrakis ((triphenylphosphine) palladium 1.16g (molecular weight 1154, 0.001mol), 2M sodium carbonate aqueous solution 80ml, toluene 80ml, ethanol 80ml. Replacement with argon After that, reflux and monitor the reaction by thin-layer chromatography (TLC). After 4 hours, TLC found that the bromide of the raw material had reacted completely with only product spots. Cool down, separate the organic layer, evaporate to dryness, and separate by column chromatography, ethyl acetate / petroleum ether After rinsing, 10.6 g of the compound represented by formula (5) with a molecular weight of 608 and a yield of 86.7% were obtained.

[0070] Product MS (m / e): 608, elemental analysis (C 46 H 28 N 2 ): Theoretical value C: 90.76%...

Embodiment 3

[0072] Synthesis of compound represented by formula (6)

[0073] The synthesis procedure is the same as in Example 2, except that 6-bromo-2-(naphthalene-2-yl)quinazoline is changed to 6-bromo-2-(naphthalene-1-yl)quinazoline, and other reagents remain unchanged. The compound represented by formula (6) is obtained.

[0074] Product MS (m / e): 608, elemental analysis (C 46 H 28 N 2 ): Theoretical value C: 90.76%, H: 4.64%, N: 4.60%; measured value C: 90.73%, H: 4.63%, N: 4.64%.

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Abstract

The present invention relates to a class of derivatives containing quinazoline groups, such compounds have the structure shown in formula (1). The quinazoline group-containing derivatives of the present invention are suitable for use as ETL materials in electroluminescence displays. The use of the material of the invention can effectively reduce the operating voltage of the organic electroluminescent device and improve the luminous efficiency of the organic electroluminescent device.

Description

Technical field [0001] The invention belongs to the field of organic electroluminescence, and specifically relates to a quinazoline group-containing Derivatives, intermediates and preparation methods thereof, and their applications in electron transport materials. Background technique [0002] The traditionally used electron transport material 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. [0003] LG Chem reported a series of pyrene derivatives in the Chinese patent CN 101003508A specification, which are used as electron transport and injection materials in electroluminescent devices to improve the luminous efficiency of the devices. Cao Yong et al. synthesized FFF-Blm4 (J. Am. Chem. Soc.; (Communication); 2008; 130(11); 3282-3283) as an electron transport and injection ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/74H01L51/54
CPCC07D239/74H10K85/615H10K85/622H10K85/626H10K85/6572
Inventor 范洪涛李银奎邵爽任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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