Aromatic heterocyclic compound used as electron transport material and application thereof

A compound and aromatic heterocycle technology, applied in the field of organic optoelectronic materials, can solve the problems of poor energy level matching, restricting the display function of OLED luminous efficiency OLED display device, low electron migration rate, etc., to achieve extended life, excellent display effect, preparation The effect of simple and easy process

Inactive Publication Date: 2021-06-25
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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  • Aromatic heterocyclic compound used as electron transport material and application thereof
  • Aromatic heterocyclic compound used as electron transport material and application thereof
  • Aromatic heterocyclic compound used as electron transport material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] The synthesis of A1, the reaction process is as follows:

[0081]

[0082] Concrete preparation process is as follows:

[0083] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of tetrahydrofuran (THF) and 200ml of water in the reaction flask, and add 1mol% Tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ). React at 120°C for 12h. After the reaction was completed, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Among them, Pd(PPh 3 ) 4 The added amount of 2-iodo-4-bromophenol is 1mol%.

[0084]Add 100mmol of M1, 300ml of dimethylformamide (DMF), 41.4g of potassium carbonate (300mmol) into the reaction flask, and react at 120°C for 12h. Afte...

Embodiment 2

[0093] The synthesis of A6, the reaction process is as follows:

[0094]

[0095] Concrete preparation process is as follows:

[0096] Add 100mmol of 2-iodo-4-bromophenol, 100mmol of 2-fluoro-4-chlorophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water in a reaction flask, and add 1mol% of Pd ( PPh 3 ) 4 . React at 120°C for 12h. After the reaction was completed, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Among them, Pd(PPh 3 ) 4 The added amount of 2-bromo-4-bromophenol is 1mol%.

[0097] Add 100mmol of M1, 300ml of DMF, 41.4g of potassium carbonate (300mmol) into the reaction flask, and react at 120°C for 12h. After the reaction was completed, water was added, and a solid precipitated o...

Embodiment 3

[0105] The synthesis of A12, the reaction process is as follows:

[0106]

[0107] Concrete preparation process is as follows:

[0108] Add 100mmol of 2-boronic acid-5-chlorobenzoic acid methyl ester, 100mmol of 3-bromoiodobenzene, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water in the reaction flask, and add 1mol% of Pd(PPh 3 ) 4 . React at 120°C for 12h. After the reaction was completed, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Among them, Pd(PPh 3 ) 4 The added amount is 1mol% of 3-bromoiodobenzene.

[0109] Add 100mmol of M1 and 200ml of THF into the reaction flask, add 220mmol of methylmagnesium bromide dropwise at 0°C, after the dropwise addition is completed, rise to room temperature and react fo...

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PUM

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Abstract

The invention provides an aromatic heterocyclic compound which can be used for 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 the organic electroluminescent device and a display device containing the compound.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to a class of aromatic heterocyclic compounds used as electron transport materials and applications thereof. Background technique [0002] Electroluminescence (EL) refers to the phenomenon that luminescent materials emit light when excited by current and voltage under the action of an electric field. It is a luminescent process that directly converts electrical energy into light energy. Organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, light weight, simple composition and process, etc. Compared with liquid crystal display, organic electroluminescent display is not It requires a backlight source, has a large viewing angle and low power, and its response speed can reach 1000 times that of a liquid crystal display, but its manufacturing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10C07D405/14H01L51/54H01L51/50
CPCC07D405/14C07D401/10H10K85/615H10K85/654H10K85/6574H10K85/6572H10K50/16
Inventor 邢其锋丰佩川李玉彬马艳胡灵峰陈跃杨阳张国选
Owner YANTAI XIANHUA CHEM TECH CO LTD
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