A kind of condensed ring aromatic hydrocarbon derivative containing naphthyridine group and its application

A technology of condensed aromatic hydrocarbons and naphthyridine groups, which is applied in the field of organic electroluminescence, can solve the problems of increasing the complexity of the device manufacturing process, disadvantages, and reducing the cost of OLEDs, so as to achieve a good ability to accept electrons, reduce operating voltage, and improve luminescence efficiency effect

Active Publication Date: 2020-12-08
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 condensed ring aromatic hydrocarbon derivative containing naphthyridine group and its application
  • A kind of condensed ring aromatic hydrocarbon derivative containing naphthyridine group and its application
  • A kind of condensed ring aromatic hydrocarbon derivative containing naphthyridine group and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1 The synthesis of various 3-bromo-7-aryl-1,5-naphthyridine derivative intermediates

[0065] Synthesis of 1,3-bromo-7-phenyl-1,5-naphthyridine

[0066]

[0067] 1000 ml three-necked flask equipped with magnetic stirring and nitrogen protection, add 5.72 g of 3,7-dibromo-1,5-naphthyridine (molecular weight 286, 0.02 mol), 2.7 g of phenylboronic acid (molecular weight 122, 0.022 mol), four ( (Triphenylphosphine) palladium 1.16g (molecular weight 1154, 0.001mol), 2M sodium carbonate aqueous solution 80ml, toluene 80ml, ethanol 80ml. After argon replacement, reflux at 80 ℃, use thin layer chromatography (TLC) method Monitor the reaction, after 4 hours TLC found that the raw material dibromo was reacted completely, only a monobromo product point. Cooling to 25 ℃, separate the organic layer, evaporate to dryness, column chromatography, ethyl acetate / petroleum ether eluting, obtain 5.77 g Target intermediate 3-bromo-7-phenyl-1,5-naphthyridine, molecular weight ...

Embodiment 2

[0075] Synthesis of compound shown in formula (14)

[0076]

[0077] 1000 ml bottle with magnetic stirring, add 5.68 g of 3-bromo-7-phenyl-1,5-naphthyridine (molecular weight 284, 0.02 mol), 9,10-di(naphthalene-2-yl)anthracene-2 - boric acid 11.0g (molecular weight 474, 0.022mol), tetrakis ((triphenylphosphine) palladium 1.16g (molecular weight 1154, 0.001mol), 2M aqueous sodium carbonate solution 80ml, toluene 80ml, ethanol 80ml. After argon replacement, Reflux at 80 DEG C, monitor the reaction with thin-layer chromatography (TLC), after 3.5 hours, TLC found that the raw material bromide reacted completely, and only the product point. Cooling, separate the organic layer, evaporate to dryness, column chromatography separation, ethyl acetate / Petroleum ether was rinsed to obtain 11.33 g of the compound represented by formula (14), with a molecular weight of 634 and a yield of 89.3%.

[0078] Product MS (m / e): 634, elemental analysis (C 48 h 30 N 2 ): theoretical value C:...

Embodiment 3

[0080] Synthesis of compound shown in formula (15)

[0081] The synthesis steps are the same as in Example 2, except that 3-bromo-7-phenyl-1,5-naphthyridine is changed to 3-bromo-7-(naphthalene-1-yl)-1,5-naphthyridine, other reagents Without changing, the compound represented by formula (15) is obtained.

[0082] Product MS (m / e): 684, elemental analysis (C 52 h 32 N 2 ): theoretical value C: 91.20%, H: 4.71%, N: 4.09%; measured value C: 91.23%, H: 4.73%, N: 4.04%, its nuclear magnetic spectrum ( 1 HNMR) see figure 1 shown.

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Abstract

The present invention relates to a class of fused-ring aromatic hydrocarbon derivatives containing naphthyridine groups, and the compounds have the structure shown in formula (1). The condensed ring aromatic hydrocarbon derivative containing naphthyridine group of the present invention is suitable as ETL material in electroluminescence display. 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 in particular relates to a naphthyridine group-containing condensed aromatic hydrocarbon derivative, an intermediate thereof, 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 -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; 13...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04H01L51/54
CPCC07D471/04H10K85/626H10K85/6572
Inventor 范洪涛李银奎邵爽任雪艳
Owner BEIJING ETERNAL MATERIAL TECH
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