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Conjugation interrupted hyperbranched polymer semiconductor optoelectronic material and its preparation and application method

A technology of hyperbranched polymers and optoelectronic materials, applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, luminescent materials, etc. The effect of promoting the application

Inactive Publication Date: 2011-12-28
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among optoelectronic polymer materials, hyperbranched polymers have the characteristics of simple synthesis process, low intermolecular force, high spectral stability and fluorescence quantum efficiency; so far, the commonly used methods for synthesizing polymer optoelectronic materials are Suzuki, Stille and other coupling polymerization reactions, however, the scarcity of precious metals, metal toxicity, and strict reaction conditions restrict the development of polymerization methods

Method used

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  • Conjugation interrupted hyperbranched polymer semiconductor optoelectronic material and its preparation and application method
  • Conjugation interrupted hyperbranched polymer semiconductor optoelectronic material and its preparation and application method
  • Conjugation interrupted hyperbranched polymer semiconductor optoelectronic material and its preparation and application method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Synthesis of 2-thiophene fluorenone

[0043] In a 100ml two-necked flask, add 2-bromofluorenone (0.9g, 0.005mol, 1eq.), thiophene boronic acid (5.00g, 38.8mmol), triphenylphosphopalladium (0.50g, 5%mmol), tetrahydrofuran / toluene (50ml), in sealing, dark, anaerobic, reaction temperature is 95 degrees centigrade, under the condition of nitrogen protection, react 30 minutes; Then inject potassium carbonate / potassium fluoride (39ml, 78mmol), continue to react for 48 hours. What needs to be added is THF / toluene, potassium carbonate / potassium fluoride are all deoxygenated solutions, and the concentration is 2mol / L. After the reaction was completed, pour ice water to quench, filter, 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 purified by column with 4:1 petroleum ether / dichloromethane and dried to obtain a fluffy yellow solid 2-thiophene fluorenon...

Embodiment 2

[0045] Embodiment 2: Synthesis of 2,7-dicarbazole fluorenone

[0046] In a 250ml two-necked flask, add 2,7-dibromofluorenone (6.72g, 20mmol), carbazole (8.00g, 48mmol), cuprous iodide (9.12g, 48mmol), potassium carbonate (16.60g, 120mmol) , 2,2'-bipyridine (0.005g), 1,10-phenanthroline (0.005g), 1,2-dichlorobenzene (2ml), in a sealed, dark, anaerobic, reaction temperature is 180 degrees Celsius , and reacted for 24 hours under the protection of nitrogen. After the reaction, add dichloromethane solution to quench, filter, extract the filtrate, combine organic layers, anhydrous MgSO 4 After drying, the solvent was removed by rotary evaporation to obtain a crude product, which was purified and dried by column with 6:1 petroleum ether and dichloromethane to obtain a light yellow solid 2,7-dicarbazole fluorenone. The isolated yield is 57%, and the infrared, nuclear magnetic and mass spectrometry data of this compound are as follows:

[0047] IR (KBr) v 3055, 2958, 2848, 1720, 15...

Embodiment 3

[0048] Example 3: Synthesis of p-bromooctyloxybenzene-2,7-(dithiophen-2-yl)-9 hydrogen-fluorenol

[0049] In a 250ml three-necked flask, 2,7-dithiophene fluorenone (1.12g, 3.3mmol) dissolved in 50ml of dichloromethane was slowly added dropwise to the Grignard reagent p-bromomagnesium octyloxybenzene through a constant pressure dropping funnel. (2.65g, 9.3mmol), reacted for 18 hours under the conditions of sealing, reaction temperature of 55 degrees centigrade and nitrogen protection. After the reaction was completed, add saturated ammonium chloride solution to quench, filter, extract the filtrate, combine the organic layers, anhydrous MgSO 4 Drying, rotary evaporation to remove the solvent to obtain the crude product, column purification and drying with 2:1 petroleum ether / dichloromethane to obtain white solid 9-p-bromooctyloxybenzene-2,7-(thiophen-2-yl)- 9 Hydrogen-fluorenol. The isolated yield is 79%, and the infrared, nuclear magnetic and mass spectrometry data of this co...

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PUM

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Abstract

Conjugation interrupted polymer semiconductor materials and their preparation and application methods belong to the field of organic photoelectric materials technology, and have potential important applications in the fields of light-emitting diodes, solar cells, phosphorescent host materials, organic electrical storage materials, porous materials, and gas sensing. . The conjugation interrupted polymer semiconductor material of the present invention has the following structure: the material has the advantages of high stability and simple synthesis route. This type of conjugation interrupted hyperbranched polymer semiconductor photoelectric material is prepared by Friedel-Crafts polymerization catalyzed by boron trifluoride ether at room temperature; the raw material is cheap, the operation is simple, the preparation is at normal temperature, and the yield is high.

Description

technical field [0001] The present invention specifically relates to the synthesis of fluorene conjugated interrupted hyperbranched polymer semiconductor optoelectronic materials by a new polymerization method, the steps and raw materials used in the synthesis process, and relates to the application of such materials in organic electroluminescence and organic electrical storage. Applications in optoelectronic fields such as phosphorescent host materials. Background technique [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.; -emitting Diodes) and Polymeric 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 optoelectronic industries, including fields such as organic field ...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/54H01L51/30
Inventor 黄维解令海刘正东常永正欧昌金殷成蓉仪明东钱妍石乃恩张广维
Owner NANJING UNIV OF POSTS & TELECOMM
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