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Carbazole organic semiconductor materials, methods for preparing and using same

A technology of organic semiconductors and application methods, applied in the fields of semiconductor/solid-state device manufacturing, semiconductor devices, organic chemistry, etc., can solve problems such as lack of synthesis methods, and achieve the effect of simple synthesis routes

Inactive Publication Date: 2009-07-29
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Azafluorene and its derivatives are important pyridine units with good electron acceptor ability, however, there are still no related reports due to the lack of synthetic methods

Method used

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  • Carbazole organic semiconductor materials, methods for preparing and using same
  • Carbazole organic semiconductor materials, methods for preparing and using same
  • Carbazole organic semiconductor materials, methods for preparing and using same

Examples

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preparation example Construction

[0047] A method for preparing an azafluorene-based organic semiconductor material. The compound material I is prepared from 2-bromoazafluorenone or 2-iodoazafluorenone, and has the following structure:

[0048]

[0049] Its 2-bromoazafluorenone synthesis method is as follows: its 2-bromoazafluorenone synthesis method is as follows: take phenanthroline and KBr and place them in a 100ml single-necked flask, carefully add the mixed concentrated nitric acid and concentrated sulfuric acid to the reaction flask , the temperature is between 80-170 degrees, and the reflux time is 5-24 hours. After the reaction, put the reaction solution into ice water, neutralize, filter, extract the filtrate, combine the organic layers, and anhydrous MgSO 4After drying, the solvent was removed by rotary evaporation to obtain a crude product, which was subjected to column chromatography using a mixed solvent of petroleum ether and ethyl acetate as an eluent to obtain a light yellow solid product wit...

Embodiment 1

[0058] The preparation of embodiment 1,2-bromo azafluorenone:

[0059]

[0060] Get phenanthroline (2.93g, 14.8mmol) and KBr (2.11g, 17.8mmol) and place in a 100ml single-necked flask, carefully add the mixed concentrated nitric acid and concentrated sulfuric acid (18mL and 36mL) into the reaction flask, and heat to 100 ℃, keep reflux for 12 hours, after the reaction, pour the reaction solution into ice water, use NaOH solid to neutralize the solution to pH 7, filter, and use CHCl 3 The soluble solid was washed into the filtrate and washed with CHCl 3 Extract the filtrate, combine the organic layers, anhydrous MgSO 4 After drying, the solvent was removed by rotary evaporation to obtain a crude product, which was recrystallized from water to obtain a light yellow solid product with a yield of 50%.

Embodiment 2、2

[0061] The preparation of embodiment 2,2-carbazole azafluorenone:

[0062]

[0063] Add carbazole (0.7401g, 4.4262mmol), 2-bromoazafluorenone (0.5012g, 1.9203mmol), potassium carbonate (0.3197g, 2.3131mmol), cuprous iodide (0.0803g) in a 50ml round bottom flask , 0.4216mol), small pieces of 18-crown-6 and dichlorobenzene (26ml), 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, and the organic phases were combined, anhydrous MgSO 4 After drying, the solvent was removed by rotary evaporation to obtain a crude product, which was subjected to column chromatography using a mixed solvent of petroleum ether and ethyl acetate as an eluent to obtain a yellow product with a yield of 71%.

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Abstract

The invention relates to an aza-fluorine organic semiconductor material and preparation and application methods thereof, belonging to the organic photoelectric material scientific field, in particular to the aza-fluorine organic semiconductor material and the preparation method. And the material is applied to organic electronic fields of organic light emitting display, fluorescence sensing, flash memory devices, solar cells, and etc. With the structure shown above, the material has the advantages that: (1) the aza-fluorine has special electron acceptor electronic structure and opto-electrical properties; (2) the material can interact or react with metal mutually and can be applied to the sensing field; (3) synthetic route is simple, etc.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to an azafluorene-based organic semiconductor material and a preparation method thereof, and relates to the application of these materials in the fields of organic electrical storage, organic electroluminescence, organic nonlinear optics, chemical and biological sensing, and organic laser. 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 thin-film organic electroluminescent devices (Organic Light -emitting Diodes) and polymer light-emitting diodes (Polymeric Light-emitting Diodes), organic flat panel display has become another generation of market-oriented display products after liquid crystal display. At the same time, other organic electronics and op...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00H01L51/56H01L51/50H01L51/54
Inventor 黄维解令海陈琳赵祥华石乃恩
Owner NANJING UNIV OF POSTS & TELECOMM
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