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Nitrogen heterocyclic compound, display panel and display device

A nitrogen heterocyclic compound and display panel technology, applied in organic chemistry, chemical instruments and methods, luminescent materials, etc., can solve the problems of poor coverage tightness, inability to meet high refractive index, inability to achieve close packing between molecules, etc. The effect of improving external quantum efficiency, improving luminous efficiency, and increasing polarizability

Pending Publication Date: 2020-06-09
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 specific structures and materials with high refractive index and the use of materials that meet specific parameters have improved the light extraction efficiency, but there is no solution. The problem of low 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 tightness

Method used

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  • Nitrogen heterocyclic compound, display panel and display device

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Embodiment approach

[0048] According to one embodiment of the nitrogen heterocyclic compound of the present invention, the nitrogen heterocyclic compound is selected from any one of the following compounds:

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056] According to the nitrogen heterocyclic compound of the present invention, for visible light with a wavelength between 400nm and 700nm, the refractive index of the nitrogen heterocyclic compound is n≥2.0. The refractive index n≥2.0 meets the basic performance requirements of OLED devices for CPL materials, making it suitable for use as CPL materials.

[0057] According to the nitrogen heterocyclic compound of the present invention, for visible light with a wavelength of 430nm-600nm, the compound has an extinction coefficient k≤0.1. The wavelength of blue light is usually 400nm-450nm. The compound of the present invention has an extinction coefficient k≤0.1 for visible light with a wavelength of 430nm-6...

Embodiment 1

[0067] Synthesis of Compound P1

[0068] The synthetic route of compound P1 is as follows:

[0069]

[0070] (1) In a 250ml round bottom flask, add 1-1 (15mmol), diethyl malonate (35mmol) and sodium ethoxide (15mmol) into dry ethanol (100ml), under nitrogen atmosphere, 78°C The resulting mixed solution of the intermediate was added to water, then filtered through a celite pad, the filtrate was extracted with dichloromethane, washed with water, and dried with anhydrous magnesium sulfate. After filtration and evaporation, the The crude product was purified by column chromatography to obtain intermediate product 1-2.

[0071] (2) In a 250ml round bottom flask, add 1-2 (15mmol), diethylphenylamine (15mol) to dry POCl 3 (100ml), under a nitrogen atmosphere, reacted at 120°C for 6.0 hours, added the obtained intermediate mixed solution to water, then filtered through a diatomaceous earth pad, and the filtrate was extracted with dichloromethane, then washed with water, and used ...

Embodiment 2

[0077] Synthesis of Compound P17

[0078] The synthetic route of compound P17 is as follows:

[0079]

[0080] (1) In a 250ml round bottom flask, add 17-1 (15mmol), diethyl malonate (35mmol) and sodium ethoxide (15mmol) into dry ethanol (100ml), under nitrogen atmosphere, 78°C The resulting mixed solution of the intermediate was added to water, then filtered through a celite pad, the filtrate was extracted with dichloromethane, washed with water, and dried with anhydrous magnesium sulfate. After filtration and evaporation, the The crude product was purified by column chromatography to obtain intermediate product 17-2.

[0081] (2) In a 250ml round bottom flask, add 17-2 (15mmol), diethylphenylamine (15mol) to dry POCl 3 (100ml), under a nitrogen atmosphere, reacted at 120°C for 6.0 hours, added the obtained intermediate mixed solution to water, then filtered through a diatomaceous earth pad, and the filtrate was extracted with dichloromethane, then washed with water, and us...

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Abstract

The invention belongs to the technical field of OLEDs and provides a nitrogen heterocyclic compound. The structure of the nitrogen heterocyclic compound is shown as a chemical formula 1; wherein X1 and X2 each independently represent C or N, and at least one of X1 and X2 is an N atom; X3 to X7 each independently represent N or -CRa, and 1 to 4 of X3 to X7 are N atoms; Ra is selected from hydrogen,deuterium, a Cl-C20 alkyl group, a Cl-C20 alkoxy group, a Cl-C20 thioalkyl group, a C6-C30 aryl group, or a C3-C30 heteroaryl group; Ra independently exists or forms an aliphatic ring, an aromatic ring or a heteroaromatic ring with an adjacent carbon atom; Ar1 and Ar2 are each independently selected from the group consisting of a C6-C30 aryl group and a C3-C30 heteroaryl group; L1 and L2 are independently a single bond, a C6-C30 arylene group, or a C3-C30 heteroarylene group. When the nitrogen heterocyclic compound provided by the invention is used as a cap layer material of an OLED, a relatively high refractive index can be obtained, the external quantum efficiency of an organic light-emitting device can be effectively improved, and the nitrogen heterocyclic compound has a very small extinction coefficient in a blue light region (400-450 nm), hardly absorbs blue light, and is beneficial to improving the light-emitting efficiency. The invention further provides a display panel and a display device.

Description

technical field [0001] The present invention relates to the technical field of organic electroluminescence materials, in particular to a nitrogen heterocyclic compound, a display panel and a display device comprising the nitrogen heterocyclic compound. Background technique [0002] After decades of development, OLED has come a long way. Although the internal quantum efficiency of OLED is close to 100%, the external quantum efficiency is only about 20%. Most of the light emitted by OLEDs 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 the top-emitting device, an organic capping layer (CappingLayer, CPL) is evaporated on the translucent metal electrode 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 the light ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/26C09K11/06C07D401/04C07D403/04C07D405/14C07D471/04C07D401/14C07D405/04C07D409/14H01L51/54
CPCC07D239/26C09K11/06C07D401/04C07D403/04C07D405/14C07D471/04C07D401/14C07D405/04C07D409/14C09K2211/1044C09K2211/1011C09K2211/1088C09K2211/1059C09K2211/1029H10K85/653H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K59/873H10K59/879C07D403/14
Inventor 代文朋牛晶华高威张磊黄高军
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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