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Organic compound, mixture and composition and application thereof

An organic compound, a selected technology, applied in the fields of compositions, mixtures, and organic compounds, can solve problems such as insufficient stability, reduced lifetime of organic light-emitting diodes, and reduced lifetime, and achieve excellent hole transport properties and stability, and improve electrical conductivity. Luminescence efficiency and the effect of prolonging the life of the device

Pending Publication Date: 2021-06-01
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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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 or aromatic fused ring diamine derivatives 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 use voltage to make it work. Organic light-emitting diodes emit light sufficiently, which leads to problems of reduced lifetime and increased power consumption of organic light-emitting diodes
[0006] Recently, electron acceptors such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1, 4-Benzoquinodimethane (F4TCNQ) (ChemicalScience 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, such as: unstable operation in the fabrication process of organic light emitting diodes, insufficient stability when driving organic light emitting diodes, Decreased lifetime, 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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  • Organic compound, mixture and composition and application thereof
  • Organic compound, mixture and composition and application thereof
  • Organic compound, mixture and composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0147] Embodiment 1, the synthetic reaction of compound P-1

[0148]

[0149] Synthesis of compound A2:

[0150] Compound A1 (2.02g, 10mmol), sodium periodate (NaIO 4 17.6g, 81.8mmol), ruthenium trichloride (RuCl 3. XH 2 (0, 0.25g, 1.2mmol), acetonitrile 40ml, dichloromethane 40ml, and distilled water 50ml stirred overnight at 30-40 degrees Celsius, the reaction product was cooled to room temperature, and 200ml distilled water was added, then the precipitate formed by filtration under reduced pressure, 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 make the residue pass through a silica gel column to obtain the product, and then remove the solvent under reduced pressure solvent and dry the product in vacuo to prepare the desired solid compound A2 (0.80 g, 31%), MS: [M+H] + =263.

[0151] Synthesis of compound P-1:

[0152] Tit...

Embodiment 2

[0153] Embodiment 2, the synthetic reaction of compound P-2

[0154]

[0155] Synthesis of compound A3:

[0156] Compound A2 (2.62g, 10mmol) prepared in Example 1 was dissolved in 80ml DMF, 7.4g (41.6mmol) NBS was dissolved in 73ml DMF solvent, and then the NBS solution was dripped into the bottom at a rate of 3-5 drops per second. solution, stir. At room temperature, after the dropwise addition, the reaction stopped, and 30ml of water was added dropwise to the reaction solution, recrystallized, and suction filtered to obtain product A3 (3.54g, 85%), MS: [M+H] + =418.

[0157] Synthesis of compound A4:

[0158] Titanium tetrachloride (9.34g, 50mmol), malononitrile (2.64g, 40mmol), compound A3 (4.18g, 10mmol) were refluxed and stirred in nitrogen-dried pyridine / dichloromethane for 24 hours, and then washed with cold concentrated hydrochloric acid Quenched, dichloromethane concentrated, then dried with anhydrous sodium sulfate, vacuum distillation, the residue was recryst...

Embodiment 3

[0161] Embodiment 3, the synthetic reaction of compound P-3

[0162]

[0163] Synthesis of Compound A2: Refer to Example 1.

[0164] Synthesis of Compound P-3:

[0165] Titanium tetrachloride (9.34g, 50mmol), compound A5 (4.36g, 40mmol), and compound A2 (2.63g, 10mmol) were stirred under reflux for 24 hours using dried pyridine / dichloromethane as a solvent under a nitrogen atmosphere, Then it was quenched with cold concentrated 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 compound P-3 (2.57g, 41%), MS:[ M+H] + =627.

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Abstract

The invention relates to an organic compound, a mixture and a composition and an application thereof, and in particular, relates to an application in an organic light-emitting diode. The organic compound disclosed by the invention, represented by a general formula (1), has excellent hole transport property and stability, can be used as a hole injection layer material in an organic electroluminescent element, and can also be used as a dopant to be doped in a hole injection layer or a hole transport layer, so that low-voltage driving can be realized, the electroluminescent efficiency can also be improved, and the device life is prolonged.

Description

[0001] This application claims the priority of the Chinese patent application with the application number 201911202496.X and the title of the invention "a pyrene quinone organic compound and its application" submitted to the China Patent Office on November 29, 2019, the entire content of which is incorporated by reference incorporated in this application. technical field [0002] The invention relates to the technical field of organic electroluminescence, in particular to an organic compound, mixture, composition and application 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 efficien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/31C07C255/51C07C25/24C07C255/52C07C205/04C07C317/44C07D271/10C07C251/20C07D307/68C07D285/12C07D333/38C07C205/09C07D519/00C07D213/61C07D471/06C09K11/06H01L51/50H01L51/54
CPCC07C255/31C07C255/51C07C25/24C07C255/52C07C205/04C07C317/44C07D271/10C07C251/20C07D307/68C07D285/12C07D333/38C07C205/09C07D519/00C07D213/61C07D471/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1048C09K2211/1051C09K2211/1062C09K2211/1088C09K2211/1092H10K85/622H10K85/653H10K85/655H10K85/6565H10K85/615H10K85/654H10K85/657H10K85/6572H10K50/15H10K50/17Y02E10/549
Inventor 谭甲辉宋鑫龙
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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