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End capped thiofuran small-molecule and polymer material, treating method and use thereof

A technology for thiophene and compounds, which is applied in the field of thiophene small molecules and polymer materials and their processing, and can solve problems such as complex preparation methods

Inactive Publication Date: 2006-03-08
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few patents on using this type of structure as a unit material to modify other easy-to-crystallize materials to make it a highly stable amorphous material, and the preparation method is complicated

Method used

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  • End capped thiofuran small-molecule and polymer material, treating method and use thereof
  • End capped thiofuran small-molecule and polymer material, treating method and use thereof
  • End capped thiofuran small-molecule and polymer material, treating method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1, 9-phenyl-fluoren-9-ol as a capping agent for the preparation of capping materials for thiophene:

[0073] 9-Phenyl-fluoren-9-ol

[0074] 9-phenyl-9H-fluoren-9-ol

[0075] Take bromo-benzene (2.1mmol) and magnesium Mg (0.502g, 2.1mmol) to react to generate Grignard reagent, and react with fluorenone (2.1mmol) dissolved in 16mL tetrahydrofuran at 60°C for 24 hours to form a large amount of white precipitate, and finally add Saturated color NHCl 4 Convert Grignard salts to alcohols. After the reaction was completed, ether was extracted, dried and rotary evaporated, and purified on a silica gel column with a mixed solvent of petroleum ether:dichloromethane (3:2) to obtain a slightly pale yellow solid tertiary alcohol (yield 90%).

[0076] GC-MS (EI-m / z): 258.1 (M + ).

[0077] 1 H NMR (400MHz, CDCl 3 , ppm): δ7.691-7.672 (d, J=7.6Hz, 2H), 7.406-7.325 (m, 6H), 7.292-7.236 (m, 5H), 2.508 (s, 1H).

[0078] 13 C NMR (CDCl 3 , ppm): δ150.658, 143.391, 139.82...

Embodiment 2

[0084] Example 2, 9-phenyl-fluoren-9-ol as a capping agent to treat 2,2'-dithiophene capping material preparation:

[0085] 5,5'-bis(9-phenyl-fluoren-9-yl)-2,2'-dithiophene

[0086] 5,5′-bis(9-phenyl-fluoren-9-yl)-2,2′-Bithiophene

[0087] Dissolve 9-phenyl-fluorene-9-ol and 2,2'-dithiophene in dichloromethane at a ratio of 2:1, add boron trifluoride-ether complex dropwise at room temperature for 30 minutes , adding ethanol and water to quench the reaction, dichloromethane extraction, drying and rotary evaporation, petroleum ether: dichloromethane silica gel column purification, recrystallization with tetrahydrofuran and petroleum ether to obtain white powder solid 5,5'bis(9-phenyl- Fluoren-9-yl)-2,2'-dithiophene (92.1% yield).

[0088] MALDI-TOF-MS (m / z): 646.2 (M + ).

[0089] 1 H NMR (400MHz, CDCl 3 , ppm): δ7.759-7.74 (d, J=7.6Hz, 4H), 7.491-7.472 (d, J=7.6Hz, 4H), 7.392-7.352 (td, J=7.2Hz, J=1.2Hz, 4H), 7.303-7.257(td, J=7.6Hz, J=1.2Hz, 4H), 7.228-7.188(m, 10H), 6....

Embodiment 3

[0091] Example 3, 9-phenyl-fluoren-9-ol used as a capping agent to treat 3,3'-dithiophene capping material preparation:

[0092] 2,5,2',5'-tetrakis(9-phenyl-fluoren-9-yl)-3,3'-dithiophene

[0093] 2,5,2',5'-tetrakis(9-phenyl-fluoren-9-yl)-3,3'-bithiophene

[0094] Dissolve 9-phenyl-fluorene-9-ol and 3,3'-dithiophene in dichloromethane at a ratio of 4:1, and add boron trifluoride-diethyl ether complex dropwise at room temperature for 30 minutes , adding ethanol and water to quench the reaction, dichloromethane extraction, drying and rotary evaporation, petroleum ether: dichloromethane silica gel column purification, recrystallization with tetrahydrofuran and petroleum ether to obtain white powder solid 2,5,2′,5′-tetra (9-Phenyl-fluoren-9-yl)-3,3'-dithiophene (81.2% yield).

[0095] MALDI-TOF-MS (m / z): 1126.6 (M + ).

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Abstract

This invention relates to an organic photoelectric material containing thiophene small molecules and polymers processed by capping agent and its preparation method used in organic panel display, photovoltaic cells, organic field-effect transistors and laser, which is advantaged at: 1, the convenient and easy method with light-duty reaction, 2, having the structured high heat stability and a glass temperature.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to a capped thiophene small molecule and polymer material and its processing method, and relates to the application of this type of material in organic electroluminescence, organic field effect tubes, organic solar cells, nonlinear optics, biosensing and lasers applications in other fields. 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 optoelec...

Claims

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Application Information

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IPC IPC(8): C09K11/06H05B33/14H01L33/00H01L51/30H01L31/042
CPCY02E10/50
Inventor 黄维解令海侯晓雅
Owner FUDAN UNIV
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