Novel polyfluorene derivative-polysilicofluorene and method for preparation thereof

A technology of silfluorene and compounds, which is applied in the field of silfluorene polymers and their synthesis, can solve problems such as lack of literature reports and synthesis difficulties, and achieve good application prospects, excellent luminous performance and stability

Inactive Publication Date: 2005-08-17
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of dibromo (or iodo) silfluorene monomers that can be used for Suzuki or Yamamoto polymerization is still a difficult problem, and there is no literature report so far.

Method used

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  • Novel polyfluorene derivative-polysilicofluorene and method for preparation thereof
  • Novel polyfluorene derivative-polysilicofluorene and method for preparation thereof
  • Novel polyfluorene derivative-polysilicofluorene and method for preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of poly[(3,6-dimethoxy-9,9'-dimethyl-9-silafluorene)-co-alt-(9,9'-dioctylfluorene)]3,3'- Dimethoxybenzidine was diazotized in HBr, and brominated under the catalysis of CuBr. After 12 hours of reaction, CH 2 Cl 2Extract and spin dry the solvent to obtain crude product. The crude product was separated by column chromatography to obtain the intermediate 4,4'-dibromo-3,3'-dimethoxybiphenyl (1) as a yellow powdery solid. Intermediate (1) in glacial acetic acid with I 2 / KIO 3 Add iodine, react overnight, add 2 times water and filter to obtain a yellow solid product precipitate. The crude product was separated by column chromatography to obtain the intermediate 4,4'-dibromo-6,6'-diiodo-3,3'-dimethoxybiphenyl (2) as a light yellow powdery solid. The intermediate (2) was reacted with n-butyllithium at -100°C for half an hour, then added dichlorodimethylsilane, reacted overnight at room temperature, extracted with ether, and separated by a column to obtain a whit...

Embodiment 2

[0046] Synthesis of poly[(3,6-dimethoxy-9,9'-diphenyl-9-silafluorene)-co-alt-(2,5-dihexyloxybenzenediene)]

[0047] The intermediate (2) in Example 1 reacted with n-butyllithium at -100°C for half an hour, then added dichlorodiphenylsilane, reacted overnight at room temperature, extracted with ether, separated by column, and recrystallized several times Afterwards, a white solid 2,7-dibromo-3,6-dimethoxy-9,9'-diphenyl-9-silafluorene (denoted as A2) was obtained.

[0048] In the ethanol suspension of KOH, add the ethanol solution of hydroquinone dropwise, then add bromide n-hexane dropwise, and after reflux for 24 hours, dihexyloxybenzene is obtained, and then catalyzed with liquid bromine in the chloroform solution with ferric trichloride The reaction is to obtain 1,4-dibromo-2,5-dihexyloxybenzene, which is then catalyzed by triphenylphosphorous palladium in toluene solution to react with tributylvinyltin to obtain 1,4-diene-2, 5-Dihexyloxybenzene (marked as B2)

[0049] Equ...

Embodiment 3

[0051] Synthesis of poly[(3,6-dimethyl-9-methyl-9'-phenyl-9-silicon)-co-alt-(2,5-dihexyloxybenzenediyne)]

[0052] 3,3'-Dimethylbenzidine was diazotized in HBr, and brominated under the catalysis of CuBr. After 12 hours of reaction, CH 2 Cl 2 Extract and spin dry the solvent to obtain crude product. The crude product was separated by column chromatography to obtain the intermediate yellow powdery solid 4,4'-dibromo-3,3'-dimethylbiphenyl (1'). Intermediate (1') was treated with I in glacial acetic acid 2 / KIO 3 Add iodine, react overnight, add 2 times water and filter to obtain a yellow solid product precipitate. The crude product was separated by column chromatography to obtain the intermediate 4,4'-dibromo-6,6'-diiodo-3,3'-dimethylbiphenyl (2') as a light yellow powdery solid. The intermediate (2') was reacted with n-butyllithium at -100°C for half an hour, then added dichloromethylphenylsilane, reacted overnight at room temperature, extracted with ether, and obtained a ...

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Abstract

The present invention belongs to the field of optoelectronic material technology, and is especially polysilico fluorene with the carbon atom in the ninth position in polyfluorene substituted with silicon atom and its preparation process. Industrial materials are made to pass through four high yield reaction steps to synthesize serical silico fluorene products, and the serical silico fluorene products are then are polymerized through Suzuki, Heck, Sonogashira, Yamamoto and other processes to obtain silico fluorene homopolymers and copolymers. These polymers have excellent light emitting performance and are efficient and stable light emitting polymer materials with latent excellent application foreground in the fields of electroluminescence, photovoltaic cell, non-linear optics and sensor.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to a silicon fluorene polymer formed by replacing the carbon at the 9-position of polyfluorene with a silicon atom and a synthesis method thereof. technical background [0002] As an excellent photoelectric material, organic conjugated polymers have been widely used in batteries, photovoltaic cells, light-emitting diodes, nonlinear optics, sensors and other fields. At present, organic photoelectric materials are mainly compounds with conjugated structures composed of carbon, hydrogen, oxygen, nitrogen, sulfur, etc. Most of these compounds are electron-rich, and their ability to transport holes is much greater than that of electrons. Their HOMO And the LUMO orbital does not match the work function of the corresponding anode and cathode materials, resulting in poor luminescence performance of its single-layer device. It is necessary to add an electron trans...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F232/08C09K11/06
Inventor 黄维范曲立陈润锋
Owner FUDAN UNIV
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