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Benzoanthracene compound, preparation method of benzoanthracene compound, and organic electroluminescent device

A compound, benzanthracene technology, applied in the field of luminescent materials, can solve problems such as electronic imbalance, luminous efficiency and lifespan reduction, and achieve the effect of simple preparation method, high yield and easy availability of raw materials

Active Publication Date: 2018-04-10
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The mobility of holes is faster than that of electrons, and there will be an imbalance of electrons, and finally there will be a decrease in luminous efficiency and lifetime.

Method used

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  • Benzoanthracene compound, preparation method of benzoanthracene compound, and organic electroluminescent device
  • Benzoanthracene compound, preparation method of benzoanthracene compound, and organic electroluminescent device
  • Benzoanthracene compound, preparation method of benzoanthracene compound, and organic electroluminescent device

Examples

Experimental program
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preparation example Construction

[0041] The present invention also provides a preparation method of benzanthracene compound, comprising the following steps:

[0042] Synthesis of compound Ⅲ

[0043] Add compound I, compound II, Pd to the reaction vessel in sequence 2 (dba) 3 , P(t-Bu) 3 , NaOt-Bu, and toluene, react at 100°C, extract the organic matter with ether and water after the reaction, dry the organic layer with magnesium sulfate, and use silica gel column and recrystallization method to obtain compound III;

[0044] Synthesis of target compounds

[0045] Add compound III, compound IV, Pd to the reaction vessel in sequence 2 (dba) 3 , P(t-Bu) 3 , NaOt-Bu, and toluene, react at 100°C, extract the organic matter with dichloromethane and water after the reaction, and use silica gel column and recrystallization to obtain the target compound from the concentrated product after drying the organic layer with magnesium sulfate; The synthetic route is as follows:

[0046]

[0047] In the formula, R ...

Synthetic example 1

[0050] Synthesis of compound 1-1

[0051]

[0052] Add 2-bromo-9,9-dimethyl-9H-fluorene (37.7g, 138mmol), 7,7-dimethyl-7H-benzanthracen-3-ylamine (32.5g ,125.5mmol), Pd 2 (dba) 3 (5.74g, 6.3mmol), P(t-Bu) 3 (2.54g, 12.5mmol), NaOt-Bu (36.2g, 376.4mmol), and 1320mL of toluene were reacted at 100°C. After the reaction was completed, the organic matter was extracted with ether and water, and the organic layer was dried with magnesium sulfate, and the product was concentrated to obtain compound 1-1, 56.6 g (75%), by silica gel column and recrystallization. MS / FAB 451, calculated 451.23.

[0053] Synthesis of compound 1

[0054] Add bromobenzene (8.8g, 56.3mmol), compound 1-1 (21.2g, 46.9mmol), Pd 2 (dba) 3 (1.95g, 2.13mmol), P(t-Bu) 3 (0.86g, 4.3mmol), NaOt-Bu (12.3g, 128mmol), and 300mL of toluene were reacted at 100°C. After the reaction was completed, the organic matter was extracted with dichloromethane and water, and the concentrated product after the organic layer ...

Synthetic example 2

[0056] Synthesis of compound 2

[0057]

[0058] Using 4-bromo-biphenyl (13.2g, 56.6mmol), compound 1-1 (21.3g, 47.2mmol), Pd 2 (dba) 3 (1.97g, 2.15mmol), P(t-Bu) 3 (0.87g, 4.3mmol), NaOt-Bu (12.4g, 128.8mmol), toluene 450mL and other raw materials were synthesized according to compound 1 to obtain compound 2, 28.4g (75%). MS / FAB 603, calculated 603.29.

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Abstract

The invention aims to improve the luminous efficiency, the stability and the service life of a display device, further provides a benzoanthracene compound with a novel structure, a preparation methodof the benzoanthracene compound, and an organic electroluminescent device, and belongs to the technical field of luminescent materials. The organic electroluminescent device provided by the inventionand prepared by using the benzoanthracene compound as a hole transport layer shows high efficiency and a long service life. According to the preparation method of the benzoanthracene compound providedby the invention, raw materials are easily available, the preparation method is simple, the yield is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of luminescent materials, in particular to a benzanthracene compound, a preparation method thereof, and an organic electroluminescence device. Background technique [0002] Portable displays are now trending toward increased panel sizes, resulting in higher power consumption requirements for benchmark portable displays. Thus, the limited power supply of batteries is an important factor in the standpoint of portable displays; in addition, its efficiency and lifetime are also issues that must be addressed. The efficiency, life and driving voltage of portable display screens are mutually coherent. Generally, the efficiency increases, the driving voltage decreases, and the crystallization of organic matter caused by resistance heating occurs when the driving voltage is reduced. But improving the above organic layers cannot maximize efficiency. Because, the best combination of energy level and T1 value between each organ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C209/10C07C255/58C07C253/30C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C211/61C07C255/58C09K2211/1014C09K2211/1011C09K2211/1007H10K85/615H10K85/622H10K85/623H10K85/624H10K85/626H10K85/631H10K85/633H10K50/15
Inventor 王辉李贺孙峰赵贺李文军李明
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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