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Alcohol soluble high molecular material in poly-fluorene group containing phosphate group and preparation method

A technology of phosphate groups and polymer materials, applied in the field of optoelectronic materials, which can solve the problems of few types of polymers, low molecular weight and solubility, poor color purity, etc.

Active Publication Date: 2005-11-16
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, polyphenylene, polyphenylene, polythiophene, and polyfluorene alcohol / water-soluble materials containing quaternary ammonium salt, carboxylate, sulfonate groups have been extensively studied, and their applications in the field of biosensors It has achieved great success and can accurately detect DNA sequence fragments at the 10-18mol level; however, in the field of optoelectronics, there are still many indicators to be improved, for example, the molecular weight and solubility are low, the fluorescence quantum efficiency of solid-state thin films is low, and the charge-induced The aggregation is severe, the color purity is poor, and there are fewer types of polymers
These have greatly affected the performance of the device and need to be further improved

Method used

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  • Alcohol soluble high molecular material in poly-fluorene group containing phosphate group and preparation method
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  • Alcohol soluble high molecular material in poly-fluorene group containing phosphate group and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: 2,7-dibromo-9, the synthesis of 9-(3'-bromopropyl) fluorene

[0018] at 10 5 Under Pa argon protection, add 5g of 2,7-dibromofluorene, 30mL of 1,3-dibromopropane, 0.1g of tetrabutylammonium bromide and 30mL of 50% sodium hydroxide in a 250mL three-necked reaction flask aqueous solution, stirred and reacted at 60°C for 10 hours. After the reaction, dilute with 100mL dichloromethane solution, then wash twice with 100mL water, 100mL 1M hydrochloric acid, 100mL water, 100mL brine, and wash the organic phase with MgSO 4 After drying, the solvent was removed to obtain a crude product, which was separated by column chromatography and petroleum ether was used as eluent to obtain 5.4 g of 2,7-dibromo-9,9-(3'-bromopropyl)fluorene, which was white Solid, yield 62%.

Embodiment 2

[0019] Embodiment 2: 2,7-dibromo-9, the synthesis of 9-(4'-bromobutyl) fluorene

[0020] at 10 5 Under the protection of Pa argon, 5g of 2,7-dibromofluorene, 10.9g of 4-(4'-bromobutoxy)toluene, 50mL of toluene, 0.1g of tetrabutyl bromide were successively added into a 250mL three-necked reaction flask Ammonium chloride and 30 mL of 50% aqueous sodium hydroxide solution were stirred and reacted at 60° C. for 10 hours. After the reaction, dilute with 100mL dichloromethane solution, then wash twice with 100mL water, 100mL 1M hydrochloric acid, 100mL water, 100mL brine, and wash the organic phase with MgSO 4 After drying, the solvent was removed to obtain a crude product, which was separated by column chromatography using petroleum ether as eluent to obtain 6.3 g of white solid with a yield of 65%. Reflux 6.3g of the above product in 4mL of 48% hydrobromic acid and 20mL of glacial acetic acid mixture at 110°C for 48 hours, pour it into water, extract with 100mL of dichloromethan...

Embodiment 3

[0021] Example 3: Synthesis of 2,7-dibromo-9,9-(6'-bromohexyl)fluorene

[0022] at 10 5 Under the protection of Pa argon, 5g of 2,7-dibromofluorene, 30mL of 1,6-dibromohexane, 0.1g of tetrabutylammonium bromide and 30mL of 50% hydroxide were successively added to a 250mL three-necked reaction flask Sodium aqueous solution, the reaction conditions and treatment method were the same as in Example 1 to obtain 8.3 g of 2,7-dibromo-9,9-(6'-bromohexyl)fluorene as a white solid with a yield of 81%.

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Abstract

An alcohol-soluble high-molecular polyfluorene material containing phosphate radicals used for electroluminescent device, flat display and fluorescent sensor is prepared through linking the high-polar phosphate radical with the side chain of polyfluorene, and Yamamoto or Suzuki reaction for grafting the fluorescent dye (dibenzothiadiazole or dithiophene dibenzothiadiazole) to polyfluorene.

Description

technical field [0001] The invention belongs to the field of optoelectronic materials, and relates to an alcohol-soluble polyfluorene polymer material containing phosphate groups and a preparation method thereof. technical background [0002] In recent years, conjugated polymers have attracted great attention in the fields of light-emitting diodes, photovoltaic devices, field-effect transistors, nonlinear optics, chemical and biological sensors. The synthesis, device technology and performance indicators of this type of materials have reached or are close to commercial requirements. Alcohol / water-soluble polymers have broad application prospects in optoelectronic materials and information technology due to their special solubility. In the preparation of light-emitting diodes, multilayer devices can be prepared with a simple process; the solvents used in the preparation process are green and pollution-free; in terms of biosensing, high selectivity and high sensitivity are on...

Claims

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Application Information

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IPC IPC(8): C08G61/12
Inventor 王利祥周刚钱钢程延祥谢志元
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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