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Fluorinated triphenylamine derivative biological blue light materials and preparation method thereof

A technology of blue light materials and triphenylamine, which is applied in the direction of luminescent materials, preparation of amino compounds, organic compounds, etc., can solve the problems of restricting the development of full-color devices, narrow selection of transmission layer materials, and short life of green light materials. The preparation method is simple, the operation is convenient, and the price is reasonable

Inactive Publication Date: 2011-06-01
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One problem is that the lifespan of the currently developed blue light materials is much shorter than that of red and green light materials, which has become a bottleneck restricting the development of full-color devices.
Another problem is that the wide-bandgap blue light material has a relatively narrow choice of transport layer materials when preparing multi-layer devices.

Method used

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  • Fluorinated triphenylamine derivative biological blue light materials and preparation method thereof
  • Fluorinated triphenylamine derivative biological blue light materials and preparation method thereof
  • Fluorinated triphenylamine derivative biological blue light materials and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthetic routes such as figure 2 shown. In a 150mL flask, 2.016g (6mmol) N, N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine, 5.9mg (0.026mmol) palladium acetate, 1.382g (14.4mmol) sodium tert-butoxide, then add 60mL o-xylene, 1.7mL (14.4mmol) 3,4-difluoro-1-iodobenzene, 21mg (0.104mmol) tri-tert-butylphosphine, under nitrogen protection, 135 The reaction was carried out at constant temperature at ℃ for 12 hours. After the reaction is completed and cooled, add 60mL of distilled water, stir for 30 minutes, filter off the insoluble matter, then use a separating funnel to separate the water layer from the organic layer, and the organic layer is filtered through anhydrous MgSO 4 After drying, the solvent was evaporated to obtain a crude product. The crude product was purified by column chromatography and recrystallized from ethanol to obtain N,N'-diphenyl-N,N'-bis(3,4-difluorophenyl)-[1,1'-biphenyl]- 4,4'-Diamine, 73% yield. Solid photoluminescence (thin film, excitation wav...

Embodiment 2

[0035] Synthetic routes such as Figure 4 shown. Others are the same as embodiment 1, and the polyfluorobenzene derivative used is 2,4-difluoro-1-iodobenzene, and the catalyst used is three (dibenzylidene acetone) dipalladium (Pd 2 (dba) 3 ) and 1,1'-bis(diphenylphosphino)ferrocene (dppf), a fluorine-substituted triphenylamine derivative N,N'-diphenyl-N,N'-bis(2, 4-difluorophenyl)-[1,1'-biphenyl]-,4'-diamine, others are similar to Example 1. The yield was 61%.

Embodiment 3

[0037] Synthetic routes such as Figure 5 shown. Others are the same as embodiment 1, and the polyfluorobenzene derivative used is 2,3-difluoro-1-iodobenzene, and the catalyst used is three (dibenzylidene acetone) dipalladium (Pd 2 (dba) 3 ) and tri-tert-butylphosphine, the inert gas used is argon, and a fluorine-substituted triphenylamine derivative N, N'-diphenyl-N, N'-bis(2,3-difluorophenyl )-[1,1'-biphenyl]-4,4'-diamine, others are similar to Example 1. The yield was 68%.

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Abstract

The invention relates to fluorinated triphenylamine derivative biological blue light materials and a preparation method thereof. The fluorinated triphenylamine derivative biological blue light materials are obtained by reacting polyfluorinated benzene derivatives with N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine in the presence of a catalyst, and the structure of the fluorinated triphenylamine derivative biological blue light materials is shown below. In the invention, fluorinated tertiary aromatic amine derivative biological blue light organic electroluminescent materials with balanced hole / electron transmission performance are obtained by introducing substitutive fluorine atoms on the basis of triphenylamine compound hole transport materials, and the performance of the materials can be regulated by changing the type of the polyfluorinated benzene derivatives. The invention can be used in the field of organic electroluminescence, in particular in the preparation of organic electroluminescent diodes. R1, R2, R3, R4 and R5 are selected from H, alkyl, cycloalkyl, alkoxy, halogen, nitro, cyano and trifluoromethyl, wherein at least two or more than two of the R1, R2, R3, R4 and R5 are F.

Description

technical field [0001] The invention relates to the field of organic electroluminescent material technology and preparation methods, in particular to a class of fluorine-substituted triphenylamine derivative blue light materials and related preparation methods. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted extensive attention for their potential applications in low-cost, full-color displays. In order to obtain a full-color display, red, green and blue materials with excellent performance must be obtained at the same time. At present, in the research of organic electroluminescent materials, the performance of blue light materials is still unsatisfactory. One problem is that the lifespan of currently developed blue light materials is much shorter than that of red and green light materials, which has become a bottleneck restricting the development of full-color devices. Another problem is that the wide-bandgap blue light material has a rel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C211/56C07C209/12H01L51/54H01L51/56
Inventor 徐清熊威王清琪干宁刘新才潘晶
Owner NINGBO UNIV
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