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Nitrogen heterocyclic ring-containing organic electroluminescent compound as well as preparation method and application thereof

An electroluminescence and compound technology, applied in the field of organic electroluminescence compounds and their preparation, can solve the problems of long time, low life, complex synthesis process, etc., and achieve low ionization potential, high photothermal stability, high hole The effect of mobility

Active Publication Date: 2021-03-12
JILIN OPTICAL & ELECTRONICS MATERIALS
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Problems solved by technology

[0004] However, due to the complex synthesis process of existing organic electroluminescent compounds, which takes a long time and has a low lifespan, it is necessary to choose a more suitable and high-performance electroluminescent compound for the current industrial application requirements of OLED devices and the requirements for optoelectronic characteristics of OLED devices. In order to achieve the comprehensive characteristics of high efficiency, long life and low voltage of the device, the further development of organic electroluminescent compounds is imminent

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  • Nitrogen heterocyclic ring-containing organic electroluminescent compound as well as preparation method and application thereof
  • Nitrogen heterocyclic ring-containing organic electroluminescent compound as well as preparation method and application thereof
  • Nitrogen heterocyclic ring-containing organic electroluminescent compound as well as preparation method and application thereof

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preparation example Construction

[0056] The present invention provides a method for preparing an organic electroluminescent material containing a nitrogen heterocycle described in the technical solution, comprising the following steps:

[0057] Combine intermediate 4 with (HO) 2 -B-L-Hal 3 Reaction, obtain intermediate 5;

[0058] The intermediate 5 and Ar 3 -NH-Ar 4 The materials are reacted in a solvent to obtain an organic electroluminescent material having a structure of formula I;

[0059]

[0060] If the L is not a connecting key, then the Hal 1 、Hal 2 and Hal 3 independently selected from bromine or iodine;

[0061] If the L is a connecting bond, the intermediate 4 is directly connected to Ar 3 -NH-Ar 4 The material reacts, and the Hal 1 、Hal 2 and Hal 3 independently selected from chlorine.

[0062] In the present invention, the intermediate 4 is preferably prepared according to the following method:

[0063] React intermediate 3 with glacial acetic acid under heating conditions to ob...

Embodiment 1

[0088]

[0089] 1. Under the protection of nitrogen, add raw material A (9.80g, 50.00mmol) into a three-necked flask, add 100.00ml of anhydrous tetrahydrofuran, then cool the reaction system to -78°C, add dropwise n-BuLi (3.20g, 50.00 mmol), stirred at -78°C for 2h. Material B (3.48g, 60.00mmol) was dissolved in 35.00ml of tetrahydrofuran solution, and then added dropwise to the above reaction system. After the dropwise addition, the temperature was raised to room temperature, and stirred for 10h. Then, a saturated ammonium chloride solution was added to quench the reaction, the reaction solution was extracted three times with ethyl acetate, the organic phases were combined, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. Then the dried solid was added to the ethanol solution, and the temperature was raised to 80 ° C, stirred for 5 hours, and then the solution was filtered while hot to obtain a solid, which was then rinsed with petroleum e...

Embodiment 2

[0105]

[0106] 1. Under the protection of nitrogen, add raw material A-73 (9.80g, 50.00mmol) into a three-necked flask, add 90.00ml of anhydrous tetrahydrofuran, then cool the reaction system to -78°C, add dropwise n-BuLi (3.20g , 50.00mmol), stirred at -78°C for 2h. The raw material B-73 (10.93g, 60.00mmol) was dissolved in 100.00ml of tetrahydrofuran solution, and then added dropwise to the above reaction system. After the dropwise addition, the temperature was raised to room temperature, and stirred for 10h. Then, a saturated ammonium chloride solution was added to quench the reaction, the reaction solution was extracted three times with ethyl acetate, the organic phases were combined, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. Then the dried solid was added to the ethanol solution, and the temperature was raised to 80 ° C, stirred for 5 hours, and then the solution was filtered while hot to obtain a solid, which was then rinsed w...

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Abstract

The invention provides a nitrogen heterocyclic ring-containing organic electroluminescent compound, as well as a preparation method and application thereof. The nitrogen heterocyclic ring-containing organic electroluminescent compound has a structure as shown in a formula I in the specification. The nitrogen heterocyclic ring-containing organic electroluminescent compound is used as a hole transport material of an electroluminescent device. An amine unit has relatively low ionization potential, relatively good electron donating property and relatively high hole mobility; the molecular symmetryis reduced, the molecular conformation isomer is increased, the compound has a rigid planar structure, molecules are not easy to crystallize and aggregate, and nitrogen-containing heterocycles and other structures are introduced, so that the compound has relatively high photo-thermal stability. And the electroluminescent device using the compound as the hole transport material can improve the light-emitting efficiency, the driving voltage, the service life and the like.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic electroluminescent compound containing a nitrogen heterocycle and a preparation method and application thereof. Background technique [0002] Organic electroluminescent diode (hereinafter referred to as OLED), as an important electroluminescent device, does not need a backlight source for its active light emission, high luminous efficiency, large viewing angle, fast response speed, large temperature adaptability range, and low energy consumption. The advantages of small, lighter and thinner, flexible display and huge application prospects have attracted the attention of many researchers. In OLEDs, hole transport materials, as an important functional material, have a direct impact on the mobility of holes, and ultimately affect the luminous efficiency of OLEDs. [0003] The generation of organic electroluminescence relies on the...

Claims

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Application Information

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IPC IPC(8): C07D471/10C09K11/06H01L51/54
CPCC07D471/10C09K11/06C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1092H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572
Inventor 马晓宇汪康黄悦王进政张雪孙向南王永光
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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