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Acenaphthene quinone organic compound and application thereof

An organic compound, acenaphthylene quinone technology, applied in the field of organic electroluminescence, can solve the problems of insufficient stability, reduced lifespan of organic light-emitting diodes, decreased lifespan, etc., achieve excellent hole transport properties and stability, and improve electroluminescence efficiency. , the effect of prolonging the life of the device

Inactive Publication Date: 2020-02-04
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, some scientists use aromatic diamine derivatives (patent CN104718636A) or aromatic fused ring diamine derivatives (patent CN107922312A) as hole transport materials for organic light-emitting diodes to improve the efficiency of hole injection, but at this time It is necessary to increase the operating voltage to make the organic light-emitting diode fully luminous, which leads to the problem of reduced life of the organic light-emitting diode and increased power consumption
[0005] Recently doping electron acceptors in the hole transport layer of organic light-emitting diodes is a new approach to solve such problems, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano -1,4-Benzoquinodimethane (F4TCNQ) (Chemical Science 2018, 9(19), 4468-4476; Appl.Phys.Lett., 2018, 112(8), 083303 / 1-083303 / 2; Chemistry of Materials 2018,30(3),998-1010), however, these compounds have many defects when used for doping organic layers, for example: unstable operation in the fabrication process of organic light emitting diodes, Insufficient stability, reduced lifespan, or when vacuum evaporation is used to manufacture organic light-emitting diodes, the above-mentioned compounds will diffuse in the device and contaminate the device

Method used

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  • Acenaphthene quinone organic compound and application thereof
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  • Acenaphthene quinone organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0198] Embodiment 1 synthetic compound DPD-1

[0199]

[0200] Synthesis of compound A2:

[0201] Compound A1 (1.82g, 10mmol) was dissolved in 80ml DMF, 7.4g (41.6mmol) NBS was dissolved in 73ml DMF solvent, and then the NBS solution was added dropwise into the substrate solution at a rate of 3-5 drops per second, and stirred. At normal temperature, the reaction stopped after the dropwise addition, and 30ml of water was added dropwise to the reaction solution, recrystallized, and suction filtered to obtain product A2 (2.01g, 60%) MS: [M+H] + =338.

[0202]

[0203] Synthesis of compound A3:

[0204] Sodium tert-butoxide (2.43g, 25mmol) and malononitrile (1.32g, 20mmol) were stirred for 15min under nitrogen and dry tetrahydrofuran, and A2 (3.37g, 10mmol), Pd(PPh 3 ) 4 (3.4g, 3mmol), and cuprous iodide (3.9g, 20mmol) were then stirred at 60°C for 12 hours, then quenched with cold concentrated hydrochloric acid, concentrated in dichloromethane, dried with anhydrous so...

Embodiment 2

[0210] Embodiment 2 synthetic compound DPD-2

[0211]

[0212] Synthesis of compound DPD-2:

[0213] Compound A4 (3.11g, 10mmol), A6 (3.88g, 20mmol) and 10ml of acetic acid were heated overnight, the reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with ethanol and water to obtain DPD-2 (3.75g, 80%).

Embodiment 3

[0214] Embodiment 3 synthetic compound DPD-3

[0215]

[0216] Synthesis of compound DPD-3:

[0217] Compound A4 (3.11g, 10mmol), A7 (3.16g, 20mmol) and 10ml of acetic acid were heated overnight, the reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with ethanol and water to obtain DPD-3 (2.87g, 65%).

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Abstract

The invention relates to an acenaphthene quinone organic compound represented by a general formula (I) shown in the description and an application thereof. The acenaphthene quinone organic compound has excellent hole transport property and stability, can serve as a hole injection layer material in an organic electroluminescent cell and can also serve as a dopant doped in a hole injection layer orhole transport layer, so that driving can be carried out with low voltage, the efficiency of electroluminescence can also be increased, and the service life of a device is prolonged.

Description

[0001] This application claims the priority of a Chinese patent application with the application number 201811485434X submitted to the China Patent Office on December 06, 2018, and the title of the invention is "Acenaphthoquinone Organic Compounds and Its Application", the entire contents of which are incorporated herein by reference Applying. technical field [0002] The invention relates to the technical field of organic electroluminescence, in particular to acenaphthoquinone organic compounds and applications thereof. Background technique [0003] Organic light-emitting diodes (OLEDs) have excellent properties such as light weight, active light emission, wide viewing angle, high contrast, high luminous efficiency, low energy consumption, easy fabrication of flexible and large-size panels, and are regarded by the industry as the most promising next-generation display technology . In order to improve the luminous efficiency of organic light-emitting diodes and promote the ...

Claims

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Application Information

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IPC IPC(8): C07D241/38C07D487/06C07C255/52C07C255/42C09K11/06H01L51/50H01L51/54
CPCC07D241/38C07D487/06C07C255/52C07C255/42C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1074C09K2211/1044C07C2601/16C07C2603/54H10K85/624H10K85/631H10K85/6572H10K50/15H10K50/16H10K50/17H10K50/171H10K50/11H10K50/18
Inventor 宋鑫龙杨曦李燕妹谭甲辉李们在李先杰王煦张月潘君友
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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