Triarylamine derivative with fluoro substituent and preparation method thereof

A fluorine substituent and derivative technology, which is applied in the field of triarylamine derivatives containing fluorine substituents and their preparation, can solve the problem of less types of triarylamine derivatives, and achieves good chemical stability, simple preparation method and convenient operation. Effect

Inactive Publication Date: 2011-07-06
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are very few types of triarylamine derivatives containing fluorine substituents at present.

Method used

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  • Triarylamine derivative with fluoro substituent and preparation method thereof
  • Triarylamine derivative with fluoro substituent and preparation method thereof
  • Triarylamine derivative with fluoro substituent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The reaction route is as follows:

[0029]

[0030] Take a clean 100mL flask, add 0.912g (2mmol) 4,4'-dibromooctafluorobiphenyl, 1.277g (4.4mmol) triphenylamine-4-boronic acid, 40mL toluene, 0.116g (0.1mmol) Pd into it (PPh 3 ) 4 , 6mL (12mmol) of K 2 CO 3 The aqueous solution, under nitrogen protection, was heated to 100 °C and stirred for 48 h. After cooling, the reaction mixture was washed with a large amount of distilled water until the water layer was clarified, the organic phase was separated with a separating funnel, and the organic phase was concentrated under reduced pressure. Finally, the concentrated crude product was subjected to a chromatography column (silica gel, petroleum ether, ethyl acetate) ester eluent) to obtain triarylamine derivatives containing fluorine substituents N,N,N',N'-tetraphenyl-[2',2",3',3",5',5",6 ',6"-octafluoro-p-tetraphenyl]-4,4"'-diamine, yield 67%. Solid photoluminescence (thin film, excitation wavelength 365nm): peak wave...

Embodiment 2

[0035] The reaction route is as follows:

[0036]

[0037] Others are the same as in Example 1, the triarylamine-based boronic acid used is N-phenyl-N-(3-methylphenyl)-4-aminophenylboronic acid, and the triarylamine derivative N,N'- Diphenyl-N,N'-bis(3-methylphenyl)-[2',2",3',3",5',5",6',6"-octafluoro-p-tetraphenyl ]-4,4"'-diamine, the others were similar to Example 1. The yield was 66%. Solid state photoluminescence (thin film, excitation wavelength 365 nm): peak wavelength 453 nm.

Embodiment 3

[0039] The reaction route is as follows:

[0040]

[0041]Others are the same as in Example 1, the triarylamine-based boronic acid used is N-phenyl-N-(1-naphthyl)-4-aminophenylboronic acid, and the triarylamine derivative N,N'-diphenyl containing fluorine substituents is synthesized base-N,N'-bis(1-naphthyl)-[2',2",3',3",5',5",6',6"-octafluoro-p-tetraphenyl]-4, 4"'-diamine, otherwise similar to Example 1. Yield 56%.

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PUM

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Abstract

The invention relates to a triarylamine derivative with fluoro substituents and a preparation method thereof. The triarylamine derivative is obtained by the reaction of triarylamine boric acid and 4,4 '-dibromooctafluorobiphenyl with the presence of a catalyst, and the structure is as follows, wherein Ar1 and Ar2 are selected from phenyl and naphthyl, and each group is unsubstituted or is substituted by one or more methyl; the triarylamine derivative is applicable to blue light organic electroluminescent materials, and the preparation method is simple, practical, and convenient for operation, and the performance can be adjusted by changing Ar1 and Ar2.

Description

technical field [0001] The invention relates to the field of organic electroluminescent material technology and preparation method, in particular to a class of triarylamine derivatives containing fluorine substituents and a preparation method thereof. Background technique [0002] Organic electroluminescent devices have many advantages, such as self-luminescence, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption, low cost, etc. A generation of flat panel display terminals. In order to obtain a full-color display organic electroluminescent device, it is necessary to obtain red, green and blue light materials with excellent performance at the same time. However, in the current research on organic electroluminescent materials, the performance of blue light materials is not satisfactory. [0003] Triarylamines are typical hole-transporting materials and have good lu...

Claims

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Application Information

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IPC IPC(8): C07C211/56C07C211/58C07C209/68C09K11/06
Inventor 徐清熊威王清琪干宁刘新才潘晶
Owner NINGBO UNIV
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