Aromatic amine compound, mixture, composition and organic electronic device

A compound and aromatic amine technology, which is applied in the field of aromatic amine compounds, compositions, organic electronic devices and mixtures, can solve problems such as hole and electron transport imbalance, short device life, etc., to reduce the roll-off effect and drive voltage , The effect of reducing manufacturing costs

Pending Publication Date: 2022-01-07
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most transport materials are small molecule materials based on carbazole derivatives, which still hav...

Method used

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  • Aromatic amine compound, mixture, composition and organic electronic device
  • Aromatic amine compound, mixture, composition and organic electronic device
  • Aromatic amine compound, mixture, composition and organic electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0185] Embodiment 1 synthetic compound 1

[0186]

[0187] Synthesis of Intermediate 1-2: Intermediate 1-1 (10.0 g) was dissolved in dichloromethane (100 ml). Triethylamine (8.1 g) was slowly added dropwise in a nitrogen atmosphere at 0°C and stirred for 30 min; then trifluoromethanesulfonic anhydride (22.5 g) was added dropwise and kept stirring at 0°C for 5 h. Then wash with saturated sodium carbonate solution, separate the layers, and collect the organic phase. The solvent was removed by rotary evaporation of the organic phase, followed by column chromatography to obtain intermediate 1-2. MS (ASAP): 321.

[0188] Synthesis of Intermediate 1-4: Dissolve Intermediate 1-2 (14.8g) and Intermediate 1-3 (10.2g) in a mixed solvent of 1,4-dioxane and water (210 / 20ml), And add Pd(PPh 3 ) 4 (0.5g) and potassium carbonate (19.1g). Under nitrogen atmosphere, stir at 100°C for 6h. After cooling, most of the solvent was removed by rotary evaporation, and then extracted with dic...

Embodiment 2

[0192] Embodiment 2 synthetic compound 2

[0193]

[0194] Synthesis of Compound 2: Intermediate 1-7 (4.70g), Compound 2-1 (2.34g), Pd(dba) 2 (0.10g), TTBP (0.18g) and sodium tert-butoxide (1.50g) were dissolved in toluene and stirred at 75°C for 4h under a nitrogen atmosphere. After cooling, it was washed with water and separated, the organic phase was collected, and the organic phase was rotary evaporated to remove the solvent. The obtained crude product was subjected to column chromatography and recrystallization to obtain compound 2. MS (ASAP): 670.

Embodiment 3

[0195] Embodiment 3 synthetic compound 3

[0196]

[0197] Synthesis of intermediate 3-2: Dissolve compound 3-1 (6.0g) and o-bromoiodobenzene (8.0g) in a mixed solvent of 1,4-dioxane and water (150 / 30ml), and add Pd(PPh 3 ) 4 (0.20g) and potassium carbonate (7.8g). Under nitrogen atmosphere, stir at 100°C for 6h. After cooling, remove most of the solvent by rotary evaporation, then extract the product with dichloromethane and wash it three times with water, separate the liquids, collect the organic phase, remove the solvent by rotary evaporation of the organic phase, and then undergo column chromatography and recrystallization to obtain the intermediate 3-2. MS (ASAP): 323.

[0198] The synthesis of intermediate 3-3 refers to the synthesis of compound 2 in Example 2, except that intermediate 1-7 is replaced by intermediate 1-5. MS (ASAP):478.

[0199] The synthesis of compound 3 refers to the synthesis of compound 2, except that 1-7 is replaced by 3-3, and 2-1 is rep...

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Abstract

The invention relates to an aromatic amine compound, a mixture, a composition and an organic electronic device. The aromatic amine compound has a structure as shown in a formula (1), shows excellent hole transport property and stability, can be used as a hole transport layer material in an organic electroluminescent device, and can be used for reducing driving voltage, improving electroluminescent efficiency and prolonging the service life of the device. In addition, the roll-off effect can be reduced, and the manufacturing cost is reduced.

Description

[0001] This application claims the priority of the Chinese patent application with the application number 202010573060.8 and the title of the invention "An organic compound and its application in organic electronic devices" submitted to the China Patent Office on June 22, 2020, the entire content of which is passed References are incorporated in this application. technical field [0002] The invention relates to the technical field of organic electroluminescence, in particular to an aromatic amine compound, a mixture, a composition and an organic electronic device. Background technique [0003] Organic optoelectronic materials have diverse synthesis, relatively low manufacturing cost, and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad development potential for applications in optoelectronic devices such as flat panel displays and lighting due to their advantages of wide viewing angle, fast response time, low operating voltage, a...

Claims

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Application Information

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IPC IPC(8): C07C211/58C07C211/61C07D333/76C07D307/91H01L51/54
CPCC07C211/58C07C211/61C07D333/76C07D307/91H10K85/615H10K85/6576H10K85/6574
Inventor 张晨何锐锋李灿楷宋晶尧
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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