Compounds, organic light-emitting device comprising same, display panel and display device

An organic light-emitting device and compound technology, applied in the field of organic optoelectronic materials, can solve the problems of low triplet energy level, adjacent pixel crosstalk, slow material mobility, etc., to improve the luminous efficiency and lifespan, reduce the working voltage, and molecular torque. big effect

Active Publication Date: 2020-09-18
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are several technical problems in existing hole transport materials: first, the solubility of the material is not good, which will lead to poor cleaning effect of the evaporated film during mass production; second, the mobility of the material is too slow, which will lead to the overall degradation of the device. The voltage is too high; third, the mobility of the material is too fast, especially the lateral mobility of the material is too fast, which will cause crosstalk between adjacent pixels; fourth, the LUMO energy level of the material is too deep to effectively block the Fifth, the triplet state energy level of the material is low, which cannot effectively block the excitons in the light-emitting layer, and the luminous efficiency of the device is low
Compound H2 disclosed in CN103108859A It has good dissolution performance, but its mobility is too fast, and crosstalk may occur between adjacent pixels

Method used

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  • Compounds, organic light-emitting device comprising same, display panel and display device
  • Compounds, organic light-emitting device comprising same, display panel and display device
  • Compounds, organic light-emitting device comprising same, display panel and display device

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0100] This preparation example provides compound 134 The specific preparation method is as follows:

[0101] (1)

[0102] Under nitrogen atmosphere, in 200mL of anhydrous toluene (Tol), add raw materials in sequence: Compound A (5mmol), diphenylamine (11mmol), sodium tert-butoxide (t-BuONa) (12.5mmol), tris(dibenzylideneacetone ) Dipalladium (Pd 2 (dba)3) (0.25mmol), and 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (S-Phos) (0.75mmol), deoxygenated for 10min, heated to 110°C, reacted 24h. After the reaction is completed, cool and filter with suction, collect the filtrate, add water and dichloromethane for extraction and separation, collect the organic phase and dry it with anhydrous sodium sulfate, collect the filtrate with suction, spin off the solvent, and purify by column chromatography to obtain the intermediate B (78% yield).

[0103] LC-MS: m / z: Calculated: C34H22N2O2S2: 554.68, Found: 554.31.

[0104] (2)

[0105] Under nitrogen atmosphere, add reactant ...

preparation example 2

[0110] This preparation example provides compound 14 The specific preparation method is as follows:

[0111]

[0112] The difference between the preparation method of this organic compound 14 and Example 1 is that the 2-bromodiphenyl ether in the step (2) of Example 1 is With an equimolar amount of 2-bromotriphenylamine Instead, other raw materials, reaction steps and reaction conditions were the same as in Example 1, and finally the target product 2 was obtained (yield 62%).

[0113] LC-MS: m / z: Calculated: C70H48N4S2: 1009.29, Found: 1008.81.

[0114] Compound elemental analysis results: calculated value: C70H48N4S2 (%): C 83.30, H 4.79, N 5.55; test value: C 83.29, H 4.78, N 5.57.

preparation example 3

[0116] This preparation example provides compound 302 The specific preparation method is as follows:

[0117]

[0118] The difference between the preparation method of this organic compound 302 and Preparation Example 1 is that the 2-bromodiphenyl ether in the step (2) of Preparation Example 1 With an equimolar amount of 1-bromo-2-(1-methyl-1-phenyl-ethyl)-benzene Instead, other raw materials, reaction steps and reaction conditions were the same as those in Preparation Example 1, and finally the target product 3 was obtained (yield 60%).

[0119] LC-MS: m / z: Calculated: C64H50N2S2: 911.23, Found: 910.89.

[0120] Compound elemental analysis results: calculated value: C64H50N2S2 (%): C 84.36, H 5.53, N 3.07; test value: C 84.37, H 5.55, N 3.06.

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Abstract

The invention provides compounds, an organic light-emitting device comprising the same, a display panel and a display device. The compounds have a structure represented by a formula I. The organic light-emitting device comprises an anode, a cathode and an organic thin film layer located between the anode and the cathode, and the organic thin film layer comprises a light-emitting layer and furthercomprises one or a combination of at least two of a hole transport layer, an electron blocking layer and a light-emitting auxiliary layer; at least one of the hole transport layer, the electron blocking layer and the light-emitting auxiliary layer contains at least one of the compounds. The compounds provided by the invention have a relatively shallow HOMO energy level, a relatively shallow LUMO energy level and a relatively high triplet state energy level, have the advantages of proper hole mobility, high Tg, large molecular torque, difficult crystallization and good thermal stability, can beused in the hole transport layer, the electron blocking layer and/or the light-emitting auxiliary layer of the organic light-emitting device, reduces the working voltage of the device, improves the light-emitting efficiency of the device and prolongs the service life of the device.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a compound and an organic light-emitting device, a display panel and a display device containing the same. Background technique [0002] Organic light-emitting device (OLED device) is a light-emitting device based on organic light-emitting materials, which has attracted wide attention due to its many advantages such as high-efficiency light emission, simple manufacturing process, and large-area flexibility. At present, OLED devices have basically met the requirements of small and medium-sized displays, and are widely used in flat panel display and lighting fields such as instrumentation, high-end smartphones, and televisions. [0003] In addition to the necessary light-emitting layer, an OLED device usually contains one or more functional layers in a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22C07D493/10C07D493/22C07D495/10C07D495/22C07D519/00C07F7/08H01L51/54
CPCC07D495/22C07D519/00C07D491/22C07D493/22C07D495/10C07F7/0816C07D493/10H10K85/636H10K85/631H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K85/40C09K11/06H10K85/653H10K85/655H10K85/615H10K50/156C09K2211/1018H10K85/626H10K50/11H10K50/15H10K50/16H10K50/17H10K50/18H10K50/171
Inventor 冉佺高威牛晶华张磊代文朋
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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