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Spirofluorene xanthene material, and preparation and use thereof

A spirofluorene xanthene and xanthene technology, which is applied in the field of spirofluorene xanthene materials and their preparation, and achieves the effects of mild conditions, high glass transition temperature and high thermal stability

Inactive Publication Date: 2009-05-27
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In fact, the spirofluorene xanthene-like spiro ring has the similar advantages of spirobifluorene, but the related patents are all optoelectronic materials based on the core of spirofluorene xanthene containing phenolic hydroxyl groups, and the optoelectronic materials of pure spirofluorene xanthene have not been See the report

Method used

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  • Spirofluorene xanthene material, and preparation and use thereof
  • Spirofluorene xanthene material, and preparation and use thereof
  • Spirofluorene xanthene material, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、 2

[0033] Embodiment 1, bispyrene spirofluorene xanthene material preparation:

[0034] 2,7-Dibromospiro[fluorene-9,9′-oxanthene]

[0035]

[0036] Take a 100 ml single-necked bottle, add 2,7-dibromofluorenone (6.523g, 19.3mmol, 1 equiv) and phenol (18g, 191.4mmol, 10 equiv), and add methanesulfonic acid (5.0mL, 7.41g, 77.2mmol, d=1.48g / ml, 4 equiv) were added, heated and stirred under anhydrous and oxygen-free conditions, and reacted at 140°C for 24 hours. After the reaction, cool the reaction, add water and dichloromethane under stirring, extract, and rotary evaporate under reduced pressure to obtain the crude product, which is recrystallized and purified with ethyl acetate, and dried to obtain 7.346 g of the product, with a yield of 78%. The purity is greater than 99, and the molecular weight measured by GCMS is 488 (M + ).

[0037] 2,7-Dipyrenespiro[fluorene-9,9′-oxanthene]

[0038]

[0039] Take 1-pyreneboronic acid (0.3673g, 1.35mmol) and 2,7-dibromospiro[fluorene...

Embodiment 2

[0040] Example 2, preparation of bis(dimethylfluorenyl) spirofluorene xanthene material:

[0041] 2,7-Dibromospiro[fluorene 9,9'-oxanthene] (see Example 1)

[0042] 2,7-Di-{2,2'-[9,9'-dimethylfluorene]}spiro[fluorene-9,9'-oxanthene]

[0043]

[0044]Take 2-[9,9'-dimethylfluorene]fluoreneboronic acid (0.5800g, 2.20mmol) and 2,7-dibromospiro[fluorene-9,9'-oxanthene] (1.0800g, 1.10mmol) , mixed and dissolved in the mixed solvent of 30ml toluene and tetrahydrofuran, add catalyst Pd(PPh3) 4, (255.2mg, 5mol%) and K 2 CO 3 (4.41ml, 2mol / L), the reaction system was refluxed under nitrogen protection for 48 hours, after the reaction was completed, extracted with dichloromethane, combined organic phase, anhydrous MgSO 4 After drying, the solvent was removed by rotary evaporation to obtain a crude product, which was obtained by column chromatography using a mixed solvent of petroleum ether and ethyl acetate as an eluent, with a yield of 86%.

Embodiment 3

[0045] Embodiment 3, preparation of bis(diphenylamino)spirofluorene xanthene material:

[0046] 2,7-Dibromospiro[fluorene-9,9'-oxanthene] (see Example 1)

[0047] 2,7-bis[N,N-diphenyl]spiro[fluorene-9,9′-oxanthene]

[0048]

[0049] Take diphenylamine (0.3462g, 2.0485mmol), 2,7-dibromospiro[fluorene-9,9'-oxanthene] (0.5023g, 1.023mmol), potassium carbonate (0.1403g, 1.024mmol), iodide Cuprous (0.0411g, 0.2158mol), small pieces of 18-crown-6 and dichlorobenzene (16ml), the reaction system was refluxed for 24 hours under the protection of nitrogen. Then, the dichlorobenzene in the system was distilled off under reduced pressure, and the remaining product was extracted with dichloromethane, the organic phases were combined, dried with anhydrous MgSO4, and the solvent was removed by rotary evaporation to obtain the crude product, using a mixed solvent of petroleum ether and ethyl acetate Column chromatography as eluent gave white product in 73% yield.

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Abstract

The invention discloses a spirofluorene xanthene material and a preparation method and an application method thereof, and relates to application of the material in the fields such as organic electroluminescence, photovoltaic cell, organic electrical storage, organic nonlinear optics, chemical and biological sensing, organic laser and so on. The material has the following structure. The material has the advantages that (1) the material is prepared through a one pot process and has simple steps and mild conditions; (2) the material has the advantages of spirobifluorene materials, and shows high thermal stability and vitrification temperature; and (3) the material has high hole or electron mobility and so on. An electroluminescent device prepared by utilizing the material achieves satisfactory results in aspects such as illumination, luminous efficiency, voltage withstand stability and so on.

Description

technical field [0001] The present invention specifically relates to a spirofluorene xanthene material and a preparation method thereof, and relates to the application of these materials in the fields of organic electroluminescence, photovoltaic cells, organic electrical storage, organic nonlinear optics, chemical and biological sensing, and organic lasers. application. It belongs to the technical field of organic photoelectric materials. technical background [0002] Since 1987, the Tang Research Group of Kodak Company in the United States [Tang, C.W.; Van Slyke, S.A. Appl. Phys. Lett. Marks, R.N.; Mackay, K.; Friend, R.H.; Burn, P.L.; Holmes, A.B.Nature 1990, 347,539.] published organic and polymer fluorescent materials to make thin-film organic electroluminescent devices (Organic Light-emitting Diodes ) and Polymeric Light-emitting Diodes (Polymeric Light-emitting Diodes), organic flat-panel displays have become another generation of market-oriented display products aft...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/96C07D405/14H01L51/54
Inventor 黄维解令海梁婧刘烽陈淑芬李崇
Owner NANJING UNIV OF POSTS & TELECOMM
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