Chrysene derivative containing quinazoline group and application thereof

A quinazoline-based and quinazoline-containing technology, which is applied in the field of organic electroluminescence, can solve the problems of reducing the cost of OLEDs, increasing the complexity of the device manufacturing process, and unfavorable problems, and achieves good electron migration ability and good electron acceptance ability. Effect

Active Publication Date: 2017-04-05
BEIJING ETERNAL MATERIAL TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The device based on this hybrid electron transport layer improves the device efficiency, but increases

Method used

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  • Chrysene derivative containing quinazoline group and application thereof
  • Chrysene derivative containing quinazoline group and application thereof
  • Chrysene derivative containing quinazoline group and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The synthesis of various quinazoline derivative intermediates of embodiment 1

[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 into a 500 ml three-neck flask, then add 45 ml of anhydrous tetrahydrofuran, stir to dissolve, and cool to 0°C. At 0°C, under 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 in dry 1200ml of HCl gas. It was then concentrated, cooled to 25°C, and 30ml of isopropyl ether was added to precipitate the product. Then, under cooling and nitrogen protection, the solid product was added into 50 ml of 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, molecular weight 200, yield 89.6%.

[00...

Embodiment 2

[0067] Synthesis of compound shown in formula (5)

[0068]

[0069] 1000 ml bottle with magnetic stirring, add 6.68 g of 6-bromo-2-(naphthalene-2-yl)quinazoline (molecular weight 334, 0.02mol), 12-(naphthalene-2-yl) -6-boronic 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. Argon displacement Afterwards, reflux, monitor reaction with thin-layer chromatography (TLC) method, after 4 hours, TLC finds that raw material bromide reacts completely, has only product point.Cool down, separate organic layer, evaporate to dryness, column chromatography separation, ethyl acetate / petroleum ether After rinsing, 10.6 g of the compound represented by formula (5) was obtained, with a molecular weight of 608 and a yield of 86.7%.

[0070] Product MS (m / e): 608, elemental analysis (C 46 h 28 N 2 ): theoretical value C: 90.76%, H: 4.64%, N: ...

Embodiment 3

[0072] Synthesis of compound shown in formula (6)

[0073] The synthetic steps are 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 are unchanged, The compound represented by formula (6) was 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 invention relates to a chrysene derivative containing a quinazoline group. The structure of the chrysene derivative is shown in the formula (1). The chrysene derivative containing the quinazoline group is suitable for serving as an ETL material in an electroluminescent display. By means of the usage of the chrysene derivative containing the quinazoline group, the operating voltage of an organic electroluminescence device can be effectively reduced, and the luminous efficiency of the organic electroluminescence device is improved.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, in particular to a quinazoline group-containing Derivatives, their intermediates and their preparation methods, and their applications 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 -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 patent specification CN 101003508A in China, 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 inj...

Claims

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Application Information

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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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