Pyrene quinone organic compounds and their applications

A technology of organic compounds and quinones, which is applied in the field of organic electroluminescence, can solve problems such as insufficient stability, reduced lifetime of organic light-emitting diodes, and reduced lifetime, achieve excellent hole transport properties and stability, and improve electroluminescence efficiency , The effect of prolonging the life of the device

Active Publication Date: 2021-12-07
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 US4720432) or aromatic fused ring diamine derivatives (patent US5061569) 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] 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) (Appl.Phys.Lett., 73(22), 3202-3204(1998), Appl.Phys.Lett., 73(6), 729-731(1998) However, these compounds have many defects when they are used to dope organic layers, such as unstable operation in the fabrication process of organic light emitting diodes, insufficient stability when driving organic light emitting diodes, reduced lifetime, or When used to manufacture organic light-emitting diodes, the above compounds will diffuse in the device and contaminate the device

Method used

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  • Pyrene quinone organic compounds and their applications
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  • Pyrene quinone organic compounds and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0197] Embodiment 1 synthetic compound DPQ-1

[0198]

[0199] Synthesis of compound A2:

[0200] Compound A1 (2.02g, 10mmol), sodium periodate (NaIO 4 17.6g, 81.8mmol), ruthenium trichloride (RuCl.XH 2 (0, 0.25g1.2mmol), acetonitrile 40ml, dichloromethane 40ml, and distilled water 50ml stirred overnight at 30-40 degrees, the reaction product was cooled to room temperature, and 200ml distilled water was added, then the precipitate formed by filtration under reduced pressure was used Extract the filtrate with dichloromethane, and add anhydrous magnesium sulfate to it to remove moisture, then remove the solvent under reduced pressure, use dichloromethane as the eluent to pass the residue through a silica gel column to obtain the product, then remove the solvent under reduced pressure And the product was dried in vacuo to prepare the desired solid compound A2 (0.8g, 31%), MS: [M+H] + =263.

[0201] Synthesis of compound A3:

[0202] Compound A2 (2.62g, 10mmol) was diss...

Embodiment 2

[0211] Embodiment 2 synthetic compound DPQ-2

[0212]

[0213] Synthesis of compound DPQ-2:

[0214] Compound A5 (3.89g, 10mmol), A7 (2.16g, 20mmol) and 10ml of acetic acid were heated overnight, the reaction mixture was cooled to room temperature, the solid generated by filtration was washed with ethanol and water to obtain DPQ-2 (4g, 79 %).

Embodiment 3

[0215] Embodiment 3 synthetic compound DPQ-3

[0216]

[0217] Synthesis of compound DPQ-3:

[0218] Compound A5 (3.89g, 10mmol), A8 (4.16g, 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 DPQ-3 (4.39g, 60%).

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Abstract

The present invention relates to a kind of pyrene quinone organic compound represented by general formula (I) and application thereof. The pyrene quinone organic compound has excellent hole transport properties and stability, can be used as a hole injection layer material in an organic electroluminescent element, and can also be used as a dopant doped in a hole injection layer or a hole injection layer. In the transport layer, this can not only be driven by low voltage, but also improve the efficiency of electroluminescence and prolong the life of the device.

Description

[0001] This application claims the priority of the Chinese patent application submitted to the China Patent Office on December 06, 2018, the application number is 2018114854320, and the invention title is "a kind of pyrene quinone 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 pyrenequinone organic compounds and applications thereof. Background technique [0003] Organic light-emitting diodes (OLEDs) have great potential for applications in optoelectronic devices such as flat panel displays and lighting due to their wide variety, low manufacturing cost, and good optical and electrical properties. [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 and lifetime of the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/06C07D495/22C07D491/22C07D495/06C07D493/06C07D487/10C07C13/72C07D513/06C07F9/6568C07F9/80C07D241/38C07D471/22C07D471/16C07F7/10C07F9/6587C07D498/06H01L51/50H01L51/54
CPCC07D487/06C07D495/22C07D491/22C07D495/06C07D493/06C07D487/10C07C13/72C07D513/06C07F9/6568C07F9/80C07D241/38C07D471/22C07D471/16C07F7/10C07F9/6587C07D498/06C07C2603/94H10K85/625H10K85/655H10K85/626H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K85/40H10K50/17H10K50/15
Inventor 潘君友宋鑫龙杨曦李燕妹谭甲辉李们在李先杰王煦张月
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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