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An aromatic amine compound and its organic light-emitting device

A technology of compounds and aromatic amines, applied in the field of organic optoelectronic materials, can solve the problem of reducing the light-emitting area and achieve the effects of high refractive index, tight electron stacking, and strong intramolecular electron transfer ability

Active Publication Date: 2020-09-15
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 part where the thin film transistor is formed is opaque, the light emitting area is reduced.

Method used

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  • An aromatic amine compound and its organic light-emitting device
  • An aromatic amine compound and its organic light-emitting device
  • An aromatic amine compound and its organic light-emitting device

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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 aromatic amine compound and an organic light-emitting device thereof, and relates to the technical field of organic photoelectric materials. The arylamine compound described in the present invention adopts on the arylamine group, connects dibenzothienyl / dibenzofuryl / carbazolyl as a bridging group, and connects oxazole / thiazole / imidazole and its Derivative groups, thereby obtaining a series of compounds, which have a higher glass transition temperature, so the compound has good thermal stability, and the prepared organic light-emitting device shows the advantage of long service life, and the aromatic amine compound of the present invention has the The high efficiency can reduce the total emission loss and waveguide loss, improve the light extraction efficiency, and thus improve the luminous efficiency of the organic light-emitting device. The aromatic amine compound of the invention has good film-forming property, simple synthesis and easy operation, and can be widely used in the fields of panel display, lighting source, organic solar cell, organic photoreceptor or organic thin film transistor.

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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Patent Type & Authority Patents(China)
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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