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Aza-aromatic compound used as electron transport material and application thereof

A technology of aromatic compounds and heteroaryl groups, which is applied in the field of organic photoelectric materials, can solve the problems of OLED display device display function, low electron migration rate, and poor energy level matching that restrict OLED luminous efficiency, achieve excellent display effect, and simple preparation process Ease of application and life-prolonging effect

Inactive Publication Date: 2021-06-29
YANTAI XIANHUA CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the electron transport materials currently used in OLEDs can achieve low electron mobility and poor energy level matching with adjacent layers, which seriously restricts the luminous efficiency of OLEDs and the display function of OLED display devices.

Method used

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  • Aza-aromatic compound used as electron transport material and application thereof
  • Aza-aromatic compound used as electron transport material and application thereof
  • Aza-aromatic compound used as electron transport material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] The synthesis of A1, the reaction process is as follows:

[0085]

[0086] The specific preparation process is as follows:

[0087] 100 mmol of 2-iodo-4-bromophenol, 100 mmol of 2-fluoro-4-chlorobenzene acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of tetrahydrofuran (THF) and 200 ml of water, and 1 mol% Four (triphenylphosphine) palladium (PD (PPH) 3 ) 4 ). The reaction was reacted at 120 ° C for 12 h. After the reaction was completed, the reaction was stopped and the reaction was cooled to room temperature, add water, and the organic phase was concentrated to give a white solid, filtered, water wash, and the resulting solid was recombined with toluene to give a white powder M1. Among them, PD (PPH 3 ) 4 The addition of 1 mol% of 2-iodo-4-bromophenol was added.

[0088] 100 mmol of M1, 300 ml of dimethylformamide (DMF), 41.4 g of potassium carbonate (300 mmol), 120 ° C, reaction 12h. After the reaction is completed, add water, there is solid precipitation, filtere...

Embodiment 2

[0095] The synthesis of A6, the reaction process is as follows:

[0096]

[0097] The specific preparation process is as follows:

[0098] 100 mmol of 2-iodo-4-bromophenol, 100 mmol of 2-fluoro-4-chlorobenzene acid, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water, and 1 mol% of PD ( PPH 3 ) 4 . The reaction was reacted at 120 ° C for 12 h. After the reaction was completed, the reaction was stopped and the reaction was cooled to room temperature, add water, and the organic phase was concentrated to give a white solid, filtered, water wash, and the resulting solid was recombined with toluene to give a white powder M1. Among them, PD (PPH 3 ) 4 The addition of 1 mol% of 2-iodo-4-bromophenol was added.

[0099] 100 mmol of M1, 300 mL of DMF, 41.4 g of potassium carbonate (300 mmol), 120 ° C were added to 120 ° C for 12 h. After the reaction is completed, add water, there is solid precipitation, filtered to obtain intermediate M2.

[0100] 100 mmol of M2, ...

Embodiment 3

[0107] The synthesis of A12, the reaction process is as follows:

[0108]

[0109] The specific preparation process is as follows:

[0110] 100 mmol of 2-boric acid-5-chlorobenzoate, 100 mmol of 3-bromide, 41.4 g of potassium carbonate (300 mmol), 800 ml of THF and 200 ml of water, and 1 mol% of PD (PPH) 3 ) 4 . The reaction was reacted at 120 ° C for 12 h. After the reaction was completed, the reaction was stopped and the reaction was cooled to room temperature, add water, and the organic phase was concentrated to give a white solid, filtered, water wash, and the resulting solid was recombined with toluene to give a white powder M1. Among them, PD (PPH 3 ) 4 The added amount of 1 mol% of 3-bromonol isryl.

[0111] 100 mmol of M1, 200 mL of THF, 0 ° C, 0.220 mmol of methyl bromide was added dropwise, and the drip was added dropwise to the room temperature reaction for 12 h. After the reaction is completed, water, the organic phase is separated, concentrated, and the intermediate...

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PUM

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Abstract

The invention provides an aza-aromatic compound which can be used as an electron transport material. The compound has an asymmetrically substituted dibenzoheterocycle parent structure, is high in bond energy between atoms, has good thermal stability, is beneficial to solid-state accumulation between molecules, is high in electron transition capability, and can be used as an electron transport material to effectively reduce the driving voltage of an organic electroluminescent device, improve the current efficiency of the organic electroluminescent device and prolong the service life of the organic electroluminescent device. The invention also provides an organic electroluminescent device and a display device containing the compound.

Description

Technical field [0001] The present invention belongs to the technical field of organic optoelectronic material, and more particularly to a nitrogen aromatic compound used as an electron transport material and its application thereof. Background technique [0002] Electroluminescence, EL) refers to a phenomenon that the luminescent material is excited under electricity field, which is excited by current and voltage, which is a light-emitting process that directly converts electrical energy into light energy. An organic electroluminescence display (hereinafter referred to as OLED) has a series of advantages of autonomous lighting, low voltage DC drive, full curing, viewing angle, light weight, composition, and process simple, and the organic electroluminescence display compared to the liquid crystal display. The backlight is required, and the viewing angle is large, the power is low, and its response speed can reach 1000 times the liquid crystal display, which is lower than the sam...

Claims

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Application Information

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IPC IPC(8): C07D405/04C07D239/74C07D409/14C07D405/10C07D409/10C07D409/04C07D251/24C07D405/14C09K11/06H01L51/54H01L51/50
CPCC07D405/04C07D239/74C07D409/14C07D405/10C07D409/10C07D409/04C07D251/24C07D405/14C09K11/06C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K50/16
Inventor 邢其锋丰佩川刘一帆马艳胡灵峰陈跃杨阳张国选
Owner YANTAI XIANHUA CHEM TECH CO LTD
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