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Anthracene nitrogen-containing organic light-emitting compound and preparation method and application thereof

A luminescent compound, an organic technology, applied in the direction of organic chemistry, chemical instruments and methods, luminescent materials, etc., can solve different problems and achieve the effects of avoiding aggregation, good electron transport performance, thermal stability and chemical stability improvement

Active Publication Date: 2020-12-29
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tris(8-hydroxyquinoline)aluminum (Alq 3 ) has been used as an electron transport material for nearly 30 years since its invention. Although there are more data to prove that it is superior to conventional materials, its application as an electron transport material and its movement to other layers are restricted.
[0004] In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Anthracene nitrogen-containing organic light-emitting compound and preparation method and application thereof
  • Anthracene nitrogen-containing organic light-emitting compound and preparation method and application thereof
  • Anthracene nitrogen-containing organic light-emitting compound and preparation method and application thereof

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preparation example Construction

[0055] The embodiment of the present invention also provides a preparation method of an anthracene nitrogen-containing organic light-emitting compound, which is characterized in that it includes the following steps:

[0056] 1) Dissolving raw material A, raw material B and sodium tert-butoxide in toluene under the protection of an inert gas to obtain a mixture 1;

[0057] 2) Add tris(dibenzylideneacetone)dipalladium and tris(tert-butyl)phosphorus into mixture 1, and react under reflux and stirring at 100-120°C for 12 hours to obtain mixture 2;

[0058] 3) After removing impurities, washing, and extracting the mixture 2, the organic phase was combined, and then the organic phase was dried with anhydrous magnesium sulfate, filtered to remove the anhydrous magnesium sulfate, concentrated and purified to obtain an intermediate product C;

[0059] 4) At room temperature, add NBS to the dichloromethane solution of the intermediate product C to react. After the reaction is completed,...

Embodiment 1

[0070] A preparation of an anthracene nitrogen-containing organic light-emitting compound (compound 1), its specific synthesis steps are as follows:

[0071]

[0072] 1) Under nitrogen protection, raw material A-1 (50 mmol), raw material B-1 (55 mmol) and sodium tert-butoxide (150 mmol) were put into a flask and dissolved in dry toluene (200 mL). Then, Pd 2 (dba) 3 (0.56mmol) and P(t-Bu) 3 (2.8 mmol) was added to the above reactant, heated to 110° C., refluxed and stirred for 12 hours. After the reaction, diatomaceous earth was used to remove the salt and the catalyst, washed with water, and the retained organic phase was extracted with dichloromethane. The organic phases were combined, and the extract was dried over anhydrous magnesium sulfate and filtered. Then, the filtered product was concentrated under reduced pressure. And the solvent was removed using a rotary evaporator. Intermediate C-1 (23.3 g, 85% yield, Ms: 549.22) was obtained.

[0073] 2) Intermediate C...

Embodiment 2

[0077] A preparation of an anthracene nitrogen-containing organic light-emitting compound (compound 20), the specific synthesis steps are as follows:

[0078]

[0079] 1) Under nitrogen protection, raw material A-20 (50 mmol), raw material B-20 (55 mmol) and sodium tert-butoxide (150 mmol) were put into a flask and dissolved in dry toluene (200 mL). Then, the three Pd 2 (dba) 3 (0.56mmol) and P(t-Bu) 3 (2.8 mmol) was added to the above reactant, the temperature was raised to 110° C., then refluxed and stirred for 12 hours. After the reaction, diatomaceous earth was used to remove the salt and the catalyst, washed with water, and the retained organic phase was extracted with dichloromethane. The organic phases were combined, and the extract was dried over anhydrous magnesium sulfate and filtered. Then, the filtered product was concentrated under reduced pressure. And the solvent was removed using a rotary evaporator. Intermediate C-20 (25.6 g, 82% yield, Ms: 624.79) wa...

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Abstract

The invention discloses an anthracene nitrogen-containing organic light-emitting compound and a preparation method and application thereof, the specific structure of the anthracene nitrogen-containingorganic light-emitting compound is as shown in the general formula 1 in the specification, and the preparation method comprises the following steps: taking methylbenzene as a solvent; reacting the raw material A with the raw material B in the presence of sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tris(tert-butyl)phosphorus to obtain an intermediate product C, reacting the intermediate product C with NBS by taking dichloromethane as a solvent to obtain an intermediate product D, and reacting the intermediate product D with a mixed solution of methylbenzene, ethanol and water by taking a mixed solution of methylbenzene, ethanol and water as a solvent; and reacting the intermediate product D with a raw material E in the presence of potassium carbonate and tetrakis(triphenylphosphine)palladium to finally obtain the compound shown in the general formula I. The anthracene derivative provided by the invention has relatively high electron transmission performance, and can improve the electron transmission efficiency of a device and can prolong the service life of the device when being applied to an organic electroluminescent device. In addition, the preparation method provided by the invention is simple, easy to operate and suitable for industrial popularization.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, and more specifically relates to an anthracene nitrogen-containing organic light-emitting compound and its preparation method and application. Background technique [0002] Organic electroluminescent technology can be used not only to manufacture new display products, but also to make new lighting products. Its application prospects are very broad, and it is expected to replace the existing liquid crystal display and fluorescent lighting. The OLED light-emitting device is composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. Among them, the hole transport layer (HTL) is responsible for adjusting the injection speed and amount of holes, and the electron transport layer ( ETL) is responsible for regulating the injection speed and injection amount of electrons. [0003] In addition, the electron tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/06C07D471/04C07D471/14C07D487/04C07D487/14C09K11/06H01L51/54H01L51/50
CPCC07D487/04C07D471/04C07D487/14C07D471/14C07D233/06C09K11/06C09K2211/1059C09K2211/1007C09K2211/1011C09K2211/1074C09K2211/1029C09K2211/1044H10K85/615H10K85/626H10K85/654H10K85/6572H10K50/16
Inventor 马晓宇汪康张雪李贺赵贺孙峰崔建勇
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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