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Azabenzene-benzimidazole organic compound, display panel and display device

An organic compound, benzimidazole technology, applied in the field of organic electroluminescent materials, can solve the problems of inability to achieve close packing between molecules, high refractive index, and poor coverage tightness, etc., achieve high glass transition temperature, improve Luminous efficiency, effect of improving light extraction efficiency

Inactive Publication Date: 2019-01-25
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the refractive index of existing CPL materials is generally below 1.9, which cannot meet the requirements of high refractive index; amine derivatives with a specific structure with high refractive index and the use of materials that meet specific parameters improve the light extraction efficiency, but not at the same time Solve the problem of luminous efficiency (especially for blue light emitting elements)
In order to increase the molecular density and achieve high thermal stability of the materials in the prior art, the molecular structure is designed to be large and loose, and the molecules cannot be tightly packed, resulting in too many holes in the molecular gel during evaporation. Poor coverage

Method used

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  • Azabenzene-benzimidazole organic compound, display panel and display device

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Embodiment approach

[0052] According to one embodiment of the present invention, the azabenzene-benzimidazole organic compound is selected from one of the following compounds:

[0053]

[0054]

[0055] According to one embodiment of the present invention, for visible light with a wavelength between 400nm and 700nm, the azabenzene-benzimidazole organic compound has a refractive index n≥2.0.

[0056] According to one embodiment of the present invention, for visible light with a wavelength between 430nm and 700nm, the azabenzene-benzimidazole organic compound has an extinction coefficient k≤0.0.

[0057] According to one embodiment of the present invention, for visible light with a wavelength between 400nm and 700nm, the transmittance of the azabenzene-benzimidazole organic compound is >65%.

[0058] The new compound designed above can be used in the capping layer CPL of the organic layer, and can be used as a host material or a dopant material or an electron transport layer or a hole transpo...

Embodiment 1

[0087] The synthetic route of compound CP1:

[0088]

[0089] In a 250ml three-necked flask, under the protection of nitrogen, in 150ml DMF, sequentially add raw material intermediate M1 (0.012mol), intermediate M6 (0.025mol) and palladium acetate (0.0003mol), mix and stir, and then add K 3 PO 4 (0.045mol) aqueous solution, reflux reaction at a temperature of 130°C for 10h. Naturally cool to room temperature, after the reaction is over, add 100mL deionized water, then drop a few drops of 2M HCl, extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel chromatography, and finally purified to obtain the product CP1.

[0090] Compound CP1 (molecular formula C 47 h 31 N 5 ) Elemental analysis results: theoretical value: C, 84.79; H, 4.69; N, 10.52. Test values: C, 84...

Embodiment 2

[0092] The synthetic route of compound CP4:

[0093]

[0094] In a 250ml three-necked flask, under nitrogen protection, in 150ml DMF, sequentially add raw material intermediate M1 (0.012mol), intermediate M7 (0.025mol) and palladium acetate (0.0003mol), mix and stir, and then add K 3 PO 4 (0.045mol) aqueous solution, reflux reaction at a temperature of 130°C for 10h. Naturally cool to room temperature, after the reaction is over, add 100mL deionized water, then drop a few drops of 2M HCl, extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography, and finally purified to obtain the product CP4.

[0095] Compound CP4 (molecular formula C 47 h 31 N 5 ) Elemental analysis results: theoretical value: C, 84.79; H, 4.69; N, 10.52. Test values: C, 84...

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Abstract

The invention relates to the field of organic electroluminescent materials, in particular to a novel azabenzene-benzimidazole organic compound, a display panel and a display device. The azabenzene-benzimidazole organic compound has the structure shown as follows. The compound of the invention can be applied to a cover layer of an organic light-emitting device, a hole transport layer, an electron transport layer, and a light-emitting layer. The light extraction efficiency and light-emitting efficiency of a top-emitting organic photoelectric device (especially most effective for blue light pixels) can be improved, and the angular dependence of light-emitting of an OLED device (most effective for red / green light pixels) can be alleviated. Moreover, water and oxygen in an external environmentare effectively prevented, and an OLED display panel is protected from being attacked by the water and the oxygen.

Description

technical field [0001] The present application relates to the field of organic electroluminescent materials, in particular to a novel azabenzene-benzimidazole organic compound, and a display panel and a display device comprising the azabenzene-benzimidazole organic compound. Background technique [0002] After decades of development, OLED has come a long way. Although its internal quantum efficiency is close to 100%, its external quantum efficiency is only about 20%. Most of the light is confined inside the light-emitting device due to factors such as substrate mode loss, surface plasmon loss, and waveguide effect, resulting in a large amount of energy loss. [0003] In top-emitting devices, an organic capping layer (CappingLayer, CPL) is usually evaporated on the semi-transparent metal electrode Al to adjust the optical interference distance, suppress the reflection of external light, and suppress the extinction caused by the movement of surface plasmons, thereby improving...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D403/14C09K11/06H01L51/50H01L51/52H01L51/54
CPCC07D401/14C07D403/14C09K11/06C09K2211/1044C09K2211/1007C09K2211/1011C09K2211/1029H10K85/654H10K85/6572H10K50/15H10K50/16H10K50/11H10K59/873H10K59/875H10K85/324H10K85/342C09K2211/1018H10K50/17H10K50/171H10K50/844
Inventor 张磊高威朱晴牛晶华刘营安平
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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