Perylene diimide-fluorene-thiophene and (3, 4-b) pyrazine conjugated polymer and preparation method and application thereof

A technology of perylene tetracarboxylic acid diimide and conjugated polymer is applied in the field of organic compound synthesis, and can solve the problems such as the collection efficiency of the carrier electrode that is not effectively utilized, the conversion efficiency is low, and the carrier mobility is low. , to achieve the effects of easy operation and control, improved utilization, and simple preparation method

Inactive Publication Date: 2011-07-27
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research of polymer solar cells is mainly focused on the donor-acceptor blend system, and the energy conversion efficiency of the blend system of PCPDTBT and PCBM has reached 6.5% (Jin Young Kim, et al.Science 2007, 317, 222) , but still much lower than the conversion efficiency of inorganic solar cells, the main cons

Method used

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  • Perylene diimide-fluorene-thiophene and (3, 4-b) pyrazine conjugated polymer and preparation method and application thereof
  • Perylene diimide-fluorene-thiophene and (3, 4-b) pyrazine conjugated polymer and preparation method and application thereof
  • Perylene diimide-fluorene-thiophene and (3, 4-b) pyrazine conjugated polymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0049] Example 1

[0050] Preparation of N,N'-bis-(3,4,5-tri-dodecyloxybenzene)-1,7-dibromo-3,4,9,10-perylene diimide:

[0051]

[0052] The specific synthesis steps are:

[0053] Add 0.148g 1,7-dibromo-3,4,9,10-perylenetetracarboxylic anhydride, 0.54g 3,4,5-tri-dodecyloxy-1-aminobenzene and 12ml propane into the reaction flask. Acid, ultrasonically vibrate for 10 minutes to mix the reactants thoroughly, and then pass nitrogen into the reactants for 30 minutes, stop passing the nitrogen, heat the reactants to 80°C for 48 hours, cool to room temperature after the reaction is complete, add three The methyl chloride was dissolved, and the organic layer was washed with sodium bicarbonate solution to obtain a red suspension, which was filtered. Anhydrous magnesium sulfate was added to the filtrate to dry and remove water, and then spin to dry. After chromatographic column separation (dichloromethane: petroleum ether = 3:1), the product was obtained. MS (EI) m / z: 1806 (M+).

Example Embodiment

[0054] Example 2:

[0055] Preparation of 2,3-diphenyl-5.7-bis(2-thiophene)thieno[3,4-b]pyrazine:

[0056]

[0057] Dissolve 0.2mmol of 3',4'-diamino-2,2':5',2"-trithiophene and 0.28mmol of diphenylethylenedione in 10ml of methanol, and react at 60℃ for 1 hour to obtain A mixture containing the target reaction product. The mixture was subjected to column chromatography after the solvent was removed under reduced pressure, and then recrystallized for purification. MS (EI) m / z: 453 (M+).

Example Embodiment

[0058] Example 3:

[0059] Preparation of 5,7-bis(5-bromothiophene)-2,3-diphenylthieno[3,4-b]pyrazine:

[0060]

[0061] Dissolve 150 mg of 2,3-diphenyl-5.7-bis(2-thiophene)thieno[3,4-b]pyrazine, 2.5 times NBS in 10ml of THF, and react at room temperature for 28 hours to obtain the target reaction product. The solvent was removed from the reaction product under reduced pressure, and the resulting product was recrystallized in DMF. MS (EI) m / z: 610 (M+).

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Abstract

The invention discloses a perylene diimide-fluorene-thiophene and (3, 4-b) pyrazine conjugated polymer shown in a general formula (I) and a preparation method and application thereof. The invention comprising the following steps: causing 1, 7-dibromo-3, 4, 9, 10-perylene tetracid anhydride to react with 3, 4, 5-trialkyl (tri-oxygroup)-1-anline to obtain a monomer; then causing a 3', 4'-diamido-2,2': 5', 2''-terthienyl compound to react with a benzil compound to obtain a midbody; and then causing the midbody to react with N-bromosuccinimide to obtain another monomer; and under the oxygen-freecondition, causing the two monomers and the bi-boric acid ester to conduct polymerization to obtain a target product. The preparation method is simple, easy to operate and control, and suitable for industrialized production; the target product prepared by the method has good dissolubility, has strong absorbance and wide absorption range when being used in the field of organic solar cell, and can be extended to a near infrared region, thus improving the utilization rate of the sunlight.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a perylene tetracarboxylic acid diimide-fluorene-thienopyrazine conjugated polymer and a preparation method and application thereof. Background technique [0002] The preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. Silicon solar cells currently used on the ground are limited in application due to complex production processes and high costs. In order to reduce the cost and expand the scope of application, people have been looking for new solar cell materials for a long time. Polymer solar cells have attracted much attention due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating and printing. If the energy conversion efficiency can be improved to be close ...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D519/00C09K11/06H01L51/00
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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