Fused ring compound containing thiophene oxide and application thereof

A technology of compound and thiophene, 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, improve electroluminescence efficiency, The effect of prolonging life

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

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.
[0005] 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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  • Fused ring compound containing thiophene oxide and application thereof
  • Fused ring compound containing thiophene oxide and application thereof
  • Fused ring compound containing thiophene oxide and application thereof

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specific Embodiment

[0148] The synthesis method of the compound of the present invention is exemplified, but the present invention is not limited to the following examples.

[0149] 1. Compounds and synthetic steps

[0150]

Embodiment 1

[0151] Embodiment 1: the synthesis of compound PD-1

[0152]

[0153] (1) Synthesis of intermediate 2:

[0154] Dissolve compound 1 (1mmol) and propanedicyanide (3.5mmol) in 50mL of anhydrous chloroform, then add 4mL of titanium tetrachloride and 4mL of pyridine, stir and reflux under nitrogen protection for 24h, add ice water after the reaction, and precipitate After filtration, 132 mg of intermediate 2 was obtained with a yield of 42%.

[0155] (2) Synthesis of Compound PD-1:

[0156] Add 30% hydrogen peroxide (0.3ml, 5.35mmol) in a 100mL three-necked flask, add trifluoroacetic anhydride (0.6ml, 4.25mmol) dropwise under ice-cooling, stir for 30min, then add intermediate 2 (111mg, 0.35mmol) dropwise ) in dichloromethane solution 15ml, reacted overnight. Slowly pour the reaction solution into ice water, adjust the pH value to 9 with sodium bicarbonate, extract with ethyl acetate three times, wash with water three times, dry over anhydrous magnesium sulfate, separate and ...

Embodiment 2

[0158] Embodiment 2: the synthesis of compound PD-2

[0159]

[0160] (1) Synthesis of intermediate 5:

[0161] Add compound 3 (10 mmol), compound 4 (20 mmol), 15 mL of saturated aqueous sodium carbonate solution, 160 mg of triphenylphosphine, 80 mg of palladium acetate, and 80 mL of THF into the two-necked flask in turn, and pass nitrogen gas for 30 minutes, and the system is heated to 66 ° C. Reflux reaction overnight, add water to terminate the reaction, extract with EA and brine, add anhydrous magnesium sulfate to the EA phase to dry, then suction filter, and pass the filtrate through a silica gel column to obtain 3.36 g of intermediate 5 with a yield of 87%.

[0162] (2) Synthesis of Intermediate 6:

[0163] Add intermediate 5 (10mmol), KOH 23g, water 100mL, EtOH 230mL, stir, react overnight at 78°C, after the reaction, spin dry the alcohol, add hydrochloric acid to neutralize to acidity, and extract with EA to obtain 3.23g of intermediate 6. The rate is 98%.

[016...

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Abstract

The invention relates to a fused ring compound containing thiophene oxide and application thereof. The fused ring compound containing thiophene oxide has a structure as shown in a formula (I1), showsexcellent hole 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 2019109150079, and the title of the invention is "a fused ring compound containing oxythiophene and its application", 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 a condensed ring compound containing oxythiophene 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 or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D495/22C07D495/14C07F7/08H01L51/50H01L51/54
CPCC07D495/04C07D495/22C07D495/14C07F7/0816H10K85/6576H10K85/657H10K85/40H10K50/155H10K50/15H10K50/17
Inventor 温华文杨曦刘爱香宋晶尧李们在李先杰王煦张月
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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