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A dibenzonitrogen-containing seven-membered heterocyclic organic compound, its preparation method and organic electroluminescent device

An electroluminescent device and organic compound technology, applied in the field of dibenzo-nitrogen-containing seven-membered heterocyclic organic compounds and organic electroluminescent devices, can solve the problems of low lifespan, complex synthesis process, time-consuming and the like, and achieve High photothermal stability, high-purity color, not easy to aggregate effect

Active Publication Date: 2022-03-08
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 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

Method used

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  • A dibenzonitrogen-containing seven-membered heterocyclic organic compound, its preparation method and organic electroluminescent device
  • A dibenzonitrogen-containing seven-membered heterocyclic organic compound, its preparation method and organic electroluminescent device
  • A dibenzonitrogen-containing seven-membered heterocyclic organic compound, its preparation method and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] This material example provides a dibenzo nitrogen-containing seven-membered heterocyclic organic compound, the preparation method of which comprises the following steps:

[0066]

[0067] 1. Under nitrogen protection, dissolve raw material A-014 (33.00mmol) and raw material B-014 (30.00mmol) in 200.00mL 1,4-dioxane solution, add tris(dibenzylideneacetone) di Palladium (0.30mmol), tri-tert-butylphosphine (1.50mmol) and sodium tert-butoxide (60.00mmol), stir evenly, heat up to 100°C, and reflux for 4h; Salt and catalyst were removed by filtration, and the solvent was removed using a rotary evaporator to obtain solid organics. Use dichloromethane to completely dissolve the solid organic matter, then slowly add it dropwise into the petroleum ether solution, stir evenly, there is precipitation, and the solid is obtained by suction filtration, rinsed with absolute ethanol and petroleum ether in turn, and dried to prepare the intermediate 1 (14.73g, yield: 87.94%);

[006...

Embodiment 2

[0083]

[0084] 1. Under nitrogen protection, dissolve raw material A-044 (33.00mmol) and raw material B-044 (30.00mmol) in 180.00mL 1,4-dioxane solution, add tris(dibenzylideneacetone) di Palladium (0.30mmol), tri-tert-butylphosphine (1.50mmol) and sodium tert-butoxide (60.00mmol), stir evenly, heat up to 100°C, and reflux for 4h; Salt and catalyst were removed by filtration, and the solvent was removed using a rotary evaporator to obtain solid organics. Use dichloromethane to completely dissolve the solid organic matter, then slowly add it dropwise into the petroleum ether solution, stir evenly, there is precipitation, and the solid is obtained by suction filtration, rinsed with absolute ethanol and petroleum ether in turn, and dried to prepare the intermediate 1 (13.21 g, yield: 88.02%);

[0085]

[0086] 2. Under nitrogen protection, dissolve intermediate 1 (25.98mmol) and raw material C-044 (25.98mmol) in 200.00mL of toluene, ethanol and water (V toluene: V ethanol...

Embodiment 3

[0100]

[0101] 1. Under nitrogen protection, dissolve raw material A-064 (33.00mmol) and raw material B-064 (30.00mmol) in 220.00mL 1,4-dioxane solution, add tris(dibenzylideneacetone) di Palladium (0.30mmol), tri-tert-butylphosphine (1.50mmol) and sodium tert-butoxide (60.00mmol), stir evenly, heat up to 100°C, and reflux for 4h; Salt and catalyst were removed by filtration, and the solvent was removed using a rotary evaporator to obtain solid organics. Use dichloromethane to completely dissolve the solid organic matter, then slowly add it dropwise into the petroleum ether solution, stir evenly, there is precipitation, and the solid is obtained by suction filtration, rinsed with absolute ethanol and petroleum ether in turn, and dried to prepare the intermediate 1 (16.16g, yield: 88.11%);

[0102]

[0103] 2. Under nitrogen protection, dissolve intermediate 1 (26.17mmol) and raw material C-064 (26.17mmol) in 230.00mL of toluene, ethanol and water (V toluene: V ethanol:...

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Abstract

The invention discloses a dibenzonitrogen-containing seven-membered heterocyclic organic compound, a preparation method thereof and an organic electroluminescent device, which belong to the technical field of chemistry and luminescent materials. The general structural formula of the organic compound is: in the formula, Ar 1 and Ar 2 Each independently represents a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted 3-60-membered heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted Any of a substituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted C6-C30 arylamino group, and a substituted or unsubstituted 3- to 30-membered heteroarylamino group. The organic compound provided by the invention contains a benzo seven-membered ring structure, has a relatively high glass transition temperature and molecular thermal stability, and has suitable HOMO and LUMO energy levels. Through device structure optimization, the photoelectricity of organic electroluminescent devices can be effectively improved. performance and longevity.

Description

technical field [0001] The invention relates to the technical field of chemistry and luminescent materials, in particular to a dibenzonitrogen-containing seven-membered heterocyclic organic compound, a preparation method thereof and an organic electroluminescent device. 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. [0003] The most important factor determining the luminous efficiency in an organic EL device is the luminescent material. The luminescent material is required to have the following characteristics: high mobility of electrons and hol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C07D401/14C07D405/14C07D409/14C07D403/10C07D403/14C09K11/06H01L51/50H01L51/54
CPCC07D403/04C07D401/14C07D405/14C07D409/14C07D403/10C07D403/14C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1059C07B2200/05H10K85/615H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/11
Inventor 马晓宇汪康黄悦王进政陈振生王士凯孙向南
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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