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Aromatic ring pyrene quinone compound and application thereof

A compound and aromatic ring technology, applied in the field of organic electroluminescence, can solve problems such as insufficient stability, reduced lifespan, and reduced lifespan of organic light-emitting diodes, achieve excellent hole transport properties and stability, prolong life, and improve electroluminescence. The effect of luminous efficiency

Active Publication Date: 2021-03-26
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, Merck uses 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 this It is necessary to increase the operating voltage to make the organic light-emitting diode fully emit light, which leads to the problem of reduced life of the organic light-emitting diode and increased power consumption.
[0006] Recently, researchers have solved such problems by doping electron acceptors in the hole transport layer of organic light-emitting diodes, 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 they are used to dope organic layers, for example: unstable operation in the manufacturing process of organic light-emitting diodes, Insufficient stability when driving light-emitting diodes, shortening lifespan, or when organic light-emitting diodes are manufactured by vacuum evaporation, the above-mentioned compounds will diffuse in the device and contaminate the device

Method used

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  • Aromatic ring pyrene quinone compound and application thereof
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specific Embodiment

[0170] The synthesis method of the compound according to the present invention is exemplified, but the present invention is not limited to the following examples.

[0171] (1) Compound synthesis part

Embodiment 1

[0172] Embodiment 1 synthetic compound DPH-1

[0173]

[0174] Synthesis of compound A2:

[0175] 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 were 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 dry and remove moisture, then remove the solvent under reduced pressure to obtain a crude product, then use column chromatography to separate and purify (dichloromethane is the eluent) to obtain the product, and further vacuum The product was dried to prepare the desired solid compound A2 (0.8 g, yield 31%), MS: [M+H] + =263.

[0176] Synthesis of Compound A3:

[0177] Dissolve compound A2 (2.62g, ...

Embodiment 2

[0189] Embodiment 2 synthetic compound DPH-2

[0190]

[0191] Synthesis of compound DPH-2:

[0192] Under nitrogen condition, titanium tetrachloride (4.67g, 25mmol), A9 (3.08g, 20mmol), A7 (4.36g, 10mmol) was refluxed and stirred in nitrogen dry pyridine / dichloromethane for 24 hours, then concentrated with cold Quenched with hydrochloric acid, concentrated in dichloromethane, then dried with anhydrous sodium sulfate, distilled under reduced pressure, and the residue was recrystallized with DCM / MeOH to obtain DPH-2 (2.96g, yield 42%), MS: [M+H ] + =705.

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Abstract

The invention relates to an aromatic ring pyrene quinone compound, a polymer and application thereof. The aromatic ring pyrene quinone compound has a structure shown as a formula (I1), shows excellenthole transport property and stability, can be used as a hole injection layer material in an organic electroluminescent element, and can also be doped in a hole injection layer or a hole transport layer as a doping agent, so that a device can be driven at a low voltage, the electroluminescent efficiency can be improved, and the service life of the device can be prolonged.

Description

[0001] This application claims the priority right of the Chinese patent application submitted to the China Patent Office on September 26, 2019, with the application number 2019109207791, and the title of the invention is "An Aromatic Pyrenequinone Organic Compound and Its Application". References are incorporated in this application. technical field [0002] The invention relates to the technical field of organic electroluminescence, in particular to an aromatic ring parapyrenequinone compound and its application. 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 O...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/06C07D471/22C07D235/02C09K11/06H01L51/50H01L51/54
CPCC07D487/06C07D471/22C07D235/02C09K11/06C09K2211/1044C09K2211/1074H10K85/6572H10K50/17H10K50/15Y02E10/549
Inventor 宋鑫龙杨曦宋晶尧刘爱香李们在李先杰王煦张月
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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