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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, achieve good chemical stability, improve luminous efficiency, and be easy to use Effect

Inactive Publication Date: 2013-10-30
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 scheme 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 (PPh 3 ) 4 , 6 mL (12 mmol) of K 2 CO 3 Aqueous solution, under nitrogen protection, was heated to 100°C and stirred for 48h. After cooling, the reaction mixture was washed with a large amount of distilled water until the water layer was clarified, and then the organic phase was separated with a separating funnel, and the organic phase was concentrated under reduced pressure. ester eluent) to obtain triarylamine derivatives containing fluorine substituents N, N, N', N'-tetraphenyl-[2', 2", 3', 3", 5', 5", 6 ', 6"-octafluoro-p-quaterphenyl]-4,4"'-diamine, the yield is 67%. Solid photoluminescence (thin film, excitation wavelength 365nm): peak wavelength 448nm (see figure 2 ).

[0031] N, N, N', N'-tetraphenyl-[2', 2", 3', 3", 5', 5", 6', 6"-octafluoro-...

Embodiment 2

[0035] The reaction scheme is as follows:

[0036]

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

Embodiment 3

[0039] The reaction scheme is as follows:

[0040]

[0041] Others are the same as in Example 1, the triarylaminoboronic acid used is N-phenyl-N-(1-naphthyl)-4-aminophenylboronic acid, and the triarylamine derivative N containing fluorine substituents is synthesized, N'-diphenyl Base-N, N'-bis(1-naphthyl)-[2', 2", 3', 3", 5', 5", 6', 6"-octafluoro-p-quaterphenyl]-4, 4 "'-diamine, others are similar to embodiment 1. The yield is 56%.

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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 methods, 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 full-color display organic electroluminescent devices, red, green and blue materials with excellent performance must be obtained at the same time. However, in the current research on organic electroluminescent materials, the performance of blue light materials is not satisfactory. [0003] Triarylamine compounds, which are typical hole transport materials and have good lumi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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