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Arylamine compound and application thereof in organic electronic device

A compound and aromatic amine technology, applied to aromatic amine compounds and their application in organic electronic devices, can solve the problems of interfacial miscibility, interfacial erosion, etc., and achieve good solubility, good film formation, and long device life. Effect

Pending Publication Date: 2022-03-25
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the problems of interfacial miscibility and interfacial erosion in solution-processed OLEDs, it is very important to find a polymer optoelectronic material with excellent solvent resistance.

Method used

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  • Arylamine compound and application thereof in organic electronic device
  • Arylamine compound and application thereof in organic electronic device
  • Arylamine compound and application thereof in organic electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0180] Embodiment 1: the synthesis of compound HT-1

[0181]

[0182] Synthesis of intermediate 3

[0183] Carbazole (119.7mmol), 1,3-dibromo-5-fluorobenzene (143.7mmol), cesium carbonate (239.4mmol), and DMF 200ml were added to a 500ml two-necked bottle successively, and N 2 React overnight at 140 degrees under protection. After the plate reaction, cool down to room temperature, pour the reaction solution into 1000ml of water, precipitate a large amount of solids, filter, wash the filter cake three times, drain it, DCM / PE=1 / 4 beating to obtain 38g of the crude product of compound 3, and feed directly to the next step .

[0184] Synthesis of intermediate 5

[0185] Compound 3 (29.96mmol), compound 4 (29.96mmol), sodium carbonate (59.9mmol), tetrakistriphenylphosphine palladium (1g), toluene 150ml and water 50ml were added in the 500ml two-necked flask successively, N 2 React overnight at 75°C under protection. After the reaction of the boric acid was completed, the pla...

Embodiment 2

[0188] Embodiment 2: the synthesis of compound HT-2

[0189]

[0190] Synthesis of Compound HT-2

[0191] Compound 5 (10mmol), compound 7 (12mmol), sodium carbonate (35.1mmol), tetrakistriphenylphosphine palladium (0.405g), toluene 150ml and water 50ml were added in the 500ml two-necked bottle successively, N 2 React overnight at 95°C under protection. After the reaction of the boric acid was completed, the plate was cooled to room temperature, the liquid was separated, and the water phase was extracted twice with DCM. The organic phases were combined, evaporated to dryness under reduced pressure, mixed with silica gel and passed through the column, the product was passed through DCM / PE=1 / 2, evaporated to dryness under reduced pressure, and then recrystallized from DCM and PE to obtain compound HT-2 with a yield of 76%.

Embodiment 3

[0192] Embodiment 3: the synthesis of compound HT-3

[0193]

[0194] Synthesis of Intermediate 9

[0195] Compound 3 (30mmol), compound 8 (30mmol), sodium carbonate (60mmol), tetrakistriphenylphosphine palladium (1g), toluene 150ml and water 50ml are added in the 500ml two-necked flask successively, N 2 React overnight at 75°C under protection. After the reaction of the boric acid was completed, the plate was cooled to room temperature, the liquid was separated, and the water phase was extracted twice with DCM. The organic phases were combined, evaporated to dryness under reduced pressure, mixed with silica gel and passed through the column, and the product was passed through with DCM / PE=1 / 3, and evaporated to dryness under reduced pressure to obtain 6.0 g of compound 9.

[0196] Synthesis of compound HT-3

[0197] Compound 9 (10mmol), compound 10 (12mmol), sodium carbonate (35mmol), tetrakistriphenylphosphine palladium (0.405g), toluene 150ml and water 50ml were added ...

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Abstract

The invention relates to an arylamine compound and application thereof in an organic electronic device, and the arylamine compound has a structure shown in a formula (1): according to the arylamine compound, a plurality of conjugated systems are introduced on a triphenylamine unit, so that the influence of nitrogen atom lone pair electrons on a C-H bond on a triphenylamine benzene ring is effectively dispersed, and the stability of the compound is improved. The compound has a stable chemical structure and a long device service life, contains an organic functional structure unit and a group capable of generating non-conjugated bond crosslinking, and has good solubility, film-forming property and good solvent resistance after curing, so that the compound can be used as a hole transport layer material in a solution organic electroluminescent element, and can be applied to the field of organic electroluminescent devices. Therefore, the invention provides a manufacturing technical scheme which is low in manufacturing cost, high in electroluminescence efficiency and long in device service life.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to aromatic amine compounds and their application in organic electronic devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have great potential for applications in optoelectronic devices such as flat panel displays and lighting due to the synthetic versatility, relatively low fabrication cost, and excellent optical and electrical properties of organic semiconductor materials. [0003] The organic electroluminescence phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic substances. An organic electroluminescence element utilizing the organic electroluminescence phenomenon generally has a positive electrode, a negative electrode, and a structure including an organic substance layer therebetween. In order to improve the efficiency and lifespan of the organic electroluminescence element, the orga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D305/06C07D307/91C07D333/76C07D405/10C07D405/12C07D405/14C07D407/04C07D407/12C07D409/04C07D409/10C07D409/12C07D409/14H01L51/54H01L51/50
CPCC07D409/10C07D409/14C07D405/14C07D405/10C07D209/86C07D407/12C07D307/91C07D333/76C07D409/04C07D305/06C07D407/04C07D409/12C07D405/12H10K85/653H10K85/622H10K85/636H10K85/626H10K85/633H10K85/631H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K50/15Y02E10/549
Inventor 温华文刘爱香宋晶尧
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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