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Perylene quinone-based organic compounds and application thereof

An organic compound, perylenequinone technology, applied in the field of organic electroluminescence, can solve the problems of lifespan reduction, insufficient stability, lifespan of organic light-emitting diodes, etc., to prolong device life, improve electroluminescence efficiency, and excellent hole transport Effects on properties and stability

Active Publication Date: 2020-02-07
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 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
[0006] 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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  • Perylene quinone-based organic compounds and application thereof
  • Perylene quinone-based organic compounds and application thereof
  • Perylene quinone-based organic compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0204] Embodiment 1 synthetic compound DPA-1

[0205]

[0206] Synthesis of compound A2:

[0207] Compound A1 (3.92g, 10mmol), 10ml of 1mol / L NaOH solution and 20ml of distilled water were stirred at 70°C for 30min, and Br 2 1.2ml continued to stir at 70°C for 24h, then removed the solvent under reduced pressure, and used dichloromethane as the eluent to pass the residue through a silica gel column to obtain the product, then removed the solvent under reduced pressure and dried the product in vacuo to prepare The desired solid compound A2 (4.85g, 67%), MS: [M+H] + =564.

[0208] Synthesis of compound A3:

[0209]Sodium tert-butoxide (2.43g, 25mmol) and malononitrile (1.32g, 20mmol) were stirred for 15min under nitrogen and dry tetrahydrofuran, and A2 (2.82g, 5mmol), 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 a...

Embodiment 2

[0212] Embodiment 2 synthetic compound DPA-2

[0213]

[0214] Synthesis of compound A4:

[0215] Sodium tert-butoxide (2.43g, 25mmol) and 4-cyano-2,3,5,6-tetrafluorobenzonitrile (4.28g, 20mmol) were stirred for 15min under nitrogen and dry tetrahydrofuran, and at room temperature Add A2 (2.82g, 5mmol), 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 sodium sulfate, and distilled under reduced pressure , the residue was recrystallized from DCM / MeOH to afford A4 (1.28 g, 47%) MS: [M+H] + =1101.

[0216] Synthesis of compound DPA-2:

[0217] Dissolve A4 (11.00g, 10mmol) with glacial acetic acid, then cool to 0°C, then add a mixture of nitric acid and hydrobromic acid, stir at room temperature after the addition is complete, quench the reaction with distilled water, continue stirring after the solid precipit...

Embodiment 3

[0218] Embodiment 3 synthetic compound DPA-4

[0219]

[0220] Synthesis of Compound A6:

[0221] Sodium tert-butoxide (2.43g, 25mmol) and hexafluoropropane (3.04g, 20mmol) were stirred for 15min under nitrogen and dry tetrahydrofuran, and A2 (2.82g, 5mmol), 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 sodium sulfate, and distilled under reduced pressure , the residue was recrystallized from DCM / MeOH to afford A6 (1.71 g, 81%) MS: [M+H] + =849.

[0222] Synthesis of compound DPA-4:

[0223] Dissolve A6 (8.49g, 10mmol) with glacial acetic acid, then cool to 0°C, then add a mixture of nitric acid and hydrobromic acid, stir at room temperature after the addition is complete, quench the reaction with distilled water, continue stirring after the solid precipitates, and then obtain a solid , DPA-4 (4.45g, 53%...

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Abstract

The invention relates to perylene quinone-based organic compounds represented by a general formula (I) or (II) shown in the specification and an application of the compounds. The perylene quinone-based organic compounds have excellent hole-transporting properties and stability, can be used as a hole injection layer material in an organic electroluminescent device, and can also be doped in a hole injection layer or a hole transmission layer as a dopant, so that the device can be driven by using low voltage, the electroluminescence efficiency can be improved, and the service life of the device can be prolonged.

Description

[0001] This application claims the priority of the Chinese patent application submitted to the China Patent Office on December 06, 2018 with the application number 2018114854373 and the title of the invention is "a perylenequinone organic compound and its application", the entire content of which is incorporated herein by reference Applying. technical field [0002] The invention relates to the technical field of organic electroluminescence, in particular to perylenequinone organic compounds and applications thereof. Background technique [0003] Due to the advantages of various types, low manufacturing cost, and good optical and electrical properties, organic light-emitting diodes (OLEDs) have great potential in the application of optoelectronic devices such as flat panel displays and lighting. [0004] An organic light-emitting diode is composed of three parts: positive electrode, negative electrode, and an organic layer between them. In order to improve the efficiency an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/51C07C22/02C07C255/31C07D495/06C07D487/06C07D493/06C07F7/10C07F9/6568C07C205/03C07C207/02C07D471/22C07C255/35C07D487/22C07D221/18C07D495/22C07D493/22C07D471/06C07D471/16C07D237/26C07D491/22C07C255/52C07C25/24C07C251/20C07C255/58C07C255/47C07D491/06C07D497/22C07D311/78C07D495/16C07D273/01C07D209/86H01F1/42H01L51/50H01L51/54
CPCC07C255/51C07C22/02C07C255/31C07D495/06C07D487/06C07D493/06C07F7/0816C07F9/65683C07C205/03C07C207/02C07D471/22C07C255/35C07D487/22C07D221/18C07D495/22C07D493/22C07D471/06C07D471/16C07D237/26C07D491/22C07C255/52C07C25/24C07C251/20C07C255/58C07C255/47C07D491/06C07D497/22C07D311/78C07D495/16C07D273/01C07D209/86H01F1/42C07C2603/52C07C2603/54H10K85/623H10K85/625H10K85/657H10K85/6574H10K85/6576H10K85/40H10K85/6572H10K50/15H10K50/17Y02E10/549
Inventor 杨曦宋鑫龙陈佳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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