Arylamine compound and organic light-emitting device thereof

A technology of organic light-emitting devices and compounds, which is applied in the field of organic photoelectric materials, can solve problems such as the reduction of light-emitting area, and achieve the effects of high refractive index, compact electron stacking, and strong photoelectric performance

Active Publication Date: 2019-11-05
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this case, when the organic light emitting device is an active matrix device, since the

Method used

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  • Arylamine compound and organic light-emitting device thereof
  • Arylamine compound and organic light-emitting device thereof
  • Arylamine compound and organic light-emitting device thereof

Examples

Experimental program
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preparation example Construction

[0152] The preparation and formation methods of each layer in the organic light-emitting device are not particularly limited, and vacuum evaporation method, spin coating method, vapor deposition method, blade coating method, laser thermal transfer method, electrospray coating method, slit coating method can be used. Either of the cloth method and the dip coating method, the method of vacuum vapor deposition is preferably used in the present invention.

[0153] The organic light-emitting device of the present invention can be widely used in the fields of panel display, lighting source, flexible OLED, electronic paper, organic solar cell, organic photoreceptor or organic thin film transistor, signboard, signal lamp and the like.

Embodiment 1

[0161] [Example 1] Synthesis of Compound 4

[0162]

[0163] Synthesis of Intermediate I-4

[0164] Under nitrogen protection, toluene (600mL), 4-(2-benzoxazolyl)aniline (44.15g, 0.21mol), 1-brominated naphthalene (43.48g, 0.21mol), Palladium acetate (0.61 g, 0.0027 mol), sodium tert-butoxide (33.7 g, 0.351 mol) and tri-tert-butylphosphine (10.8 mL of a 1.0 M solution in toluene, 0.0108 mol). And react under the condition of reflux for 2 hours. After the reaction stopped, the mixture was cooled to room temperature, filtered with diatomaceous earth, the filtrate was concentrated, recrystallized with methanol, filtered with suction and rinsed with methanol to obtain a recrystallized solid to obtain intermediate I-4 (61.45 g, the yield was about 87 %), HPLC detection solid purity >= 98.1%.

[0165] Synthesis of Compound 4

[0166] Add toluene solvent (450ml), 2,8-dibromodibenzofuran (11.74g, 36mmol), intermediate I-4 (30.27g, 90mmol), Pd 2 (dba) 3 (990mg, 1.08mmol), BINA...

Embodiment 2

[0168] [Example 2] Synthesis of compound 11

[0169]

[0170] Synthesis of Intermediate I-11

[0171] Under the protection of nitrogen, add toluene (600mL), 4-(2-benzoxazolyl)aniline (44.15g, 0.21mol), 4-bromobiphenyl (48.95g, 0.21mol) successively into the 1L reaction flask , palladium acetate (0.61 g, 0.0027 mol), sodium tert-butoxide (33.7 g, 0.351 mol) and tri-tert-butylphosphine (10.8 mL of a 1.0 M solution in toluene, 0.0108 mol). And react under the condition of reflux for 2 hours. After the reaction stopped, the mixture was cooled to room temperature, filtered with diatomaceous earth, the filtrate was concentrated, recrystallized with methanol, filtered with suction and rinsed with methanol to obtain a recrystallized solid to obtain intermediate I-11 (66.97g, the yield was about 88 %), HPLC detection solid purity >= 98.0%.

[0172] Synthesis of compound 11

[0173] Add toluene solvent (450ml), 2,8-dibromodibenzofuran (11.74g, 36mmol), intermediate I-11 (32.62g, ...

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Abstract

The invention provides an arylamine compound and an organic light-emitting device thereof and relates to the technical field of organic photoelectric materials. According to the arylamine compound, adibenzothienyl group/dibenzofuranyl group/carbazolyl group is connected onto an arylamine group to serve as a bridging group, and oxazole/thiazole/imidazole and its derivative are connected, so that aseries of compounds are obtained, the compounds have higher glass transition temperatures and good thermal stability, and the prepared organic light-emitting device has the advantage of long servicelife. In addition, the arylamine compound is high in refractive index, can reduce total emission loss and waveguide loss and improve light extraction efficiency, thereby improving the light emitting efficiency. The arylamine compound is good in film-forming property, simple in synthesis and easy to operate, and can be widely applied to the fields of panel display, illumination light sources, organic solar cells, organic photoreceptors, organic thin film transistors and the like.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine compound and an organic light-emitting device thereof. Background technique [0002] OLED is called organic light-emitting diode or organic light-emitting display. Thin, light in weight, capable of making large-size and curved panels, etc., in recent years, OLED has been more and more applied in the display market, and has become the most potential panel display technology at present. [0003] OLED is very suitable for use in small and medium-sized panels, and has been widely recognized in the fields of mobile phones, wearable products, and VR. In addition, because OLED is an all-solid-state, non-vacuum device, it has the characteristics of anti-shock and low-temperature resistance, and it also has important applications in the military. Due to the rapid development of smart phones, tablet computers, car audio and other industries in th...

Claims

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Application Information

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IPC IPC(8): C07D413/14C07D417/14C07D405/14C07D409/14C07D413/12C09K11/06H01L51/50H01L51/54
CPCC07D413/14C07D417/14C07D405/14C07D409/14C07D413/12C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092H10K85/623H10K85/624H10K85/622H10K85/615H10K85/631H10K85/636H10K85/626H10K85/633H10K85/654H10K85/657H10K85/6576H10K85/6572H10K85/6574H10K50/11H10K50/171H10K50/18H10K50/15H10K50/16H10K50/17Y02E10/549
Inventor 赵倩刘辉韩春雪
Owner CHANGCHUN HYPERIONS TECH CO LTD
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