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Polycyclic aromatic hydrocarbon derivative containing naphthyridine group and application of polycyclic aromatic hydrocarbon derivative

A technology containing naphthyridine groups and fused-ring aromatics, which is applied in electrical components, circuits, organic chemistry, etc., can solve the problems of increasing the complexity and disadvantages of the device manufacturing process, reducing the cost of OLEDs, etc., achieving good electron acceptance and reducing The effect of operating voltage and improving luminous efficiency

Active Publication Date: 2017-04-05
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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  • Polycyclic aromatic hydrocarbon derivative containing naphthyridine group and application of polycyclic aromatic hydrocarbon derivative
  • Polycyclic aromatic hydrocarbon derivative containing naphthyridine group and application of polycyclic aromatic hydrocarbon derivative
  • Polycyclic aromatic hydrocarbon derivative containing naphthyridine group and application of polycyclic aromatic hydrocarbon derivative

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 displacement, reflux at 80 ℃, use thin layer chromatography (TLC) method Monitor the reaction, after 4 hours TLC found that the raw material dibromide had reacted completely, only the monobromide product point. Cool to 25°C, separate the organic layer, evaporate to dryness, separate by column chromatography, wash with ethyl acetate / petroleum ether, obtain 5.77 g Target intermediate 3-bromo-7-phenyl-1,5-naphthyridine,...

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 finds that the raw material bromide has reacted completely, and only the product point. Cool down, separate the organic layer, evaporate to dryness, separate by column chromatography, 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 v...

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 invention relates to a polycyclic aromatic hydrocarbon derivative containing a naphthyridine group, and the derivative has a structure as shown in formula (1). The polycyclic aromatic hydrocarbon derivative containing the naphthyridine group is suitable for being used as an ETL material in an electroluminescent display. The derivative is used, so that working voltage of an organic light-emitting device can be effectively reduced, and light emitting efficiency of the organic light-emitting device is improved.

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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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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