Copolymer containing diketopyrrolopyrrole and perylene diimide, and preparation method and application thereof

A technology of perylenetetracarboxylic diimide and diketopyrrolopyrrole, applied in the field of copolymers containing diketopyrrolopyrrole and perylenetetracarboxylic diimide and its preparation, can solve the problem of low carrier Problems such as mobility, device spectral response mismatch, and low collection efficiency of carrier electrodes

Inactive Publication Date: 2014-06-18
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research on polymer solar cells mainly focuses on the blending system of donor and acceptor, using PTB7 and PC 71 The energy conversion efficiency of the BM blend system has reached 7.4% (Y.Liang et al., Adv.Mater.; DOI: 10.1002 / adma.200903528), but it is still much lower than the conversion efficiency of inorganic solar cells, which limits the performance improvement The main constraints are: the relatively low carrier mobility of organic semiconductor devices, the spectral response of the device does not match the solar radiation spectrum, the red region of the high photon flux is not effectively utilized, and the electrode collection efficiency of carriers inferior

Method used

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  • Copolymer containing diketopyrrolopyrrole and perylene diimide, and preparation method and application thereof
  • Copolymer containing diketopyrrolopyrrole and perylene diimide, and preparation method and application thereof
  • Copolymer containing diketopyrrolopyrrole and perylene diimide, and preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0038] In addition, this embodiment also provides a method for preparing a copolymer containing diketopyrrolopyrrole and perylenetetracarboxylic diimide, including the following steps:

[0039] Step 1, provide compound A and compound B, the structural formula of compound A is: The structural formula of compound B is: where R 1 for C 1 ~C 20 Alkyl or R 2 , R 3 , R 4 for H, C 1 ~C 20 Alkyl or C 1 ~C 20 The alkoxyl group, R 5 , R 6 , R 7 for H or C 1 -C 20 of alkyl.

[0040] Step 2, under anaerobic conditions, compound A and compound B are heated and refluxed in a catalyst and a solvent for 24 to 72 hours according to a molar ratio of 1 to 2:1, and after separation and purification, diketopyrrolopyrrole and perylene are obtained. Copolymer of tetracarboxylic diimide.

[0041] Preferably, in this embodiment, the catalyst is an organic palladium catalyst or a mixture of an organic palladium catalyst and an organic phosphine ligand. Wherein, the molar ratio of ...

Embodiment 1

[0054] Example 1: Dithiophene-pyrrolo[3,4-c]pyrrole diketope-N,N'-dioctyl-3,4,9,10-perylenetetracarboxylic acid diimides of this example Copolymers have the following structural formula:

[0055]

[0056] The preparation process of above-mentioned polymer is as follows:

[0057] The synthesis of the compound N,N'-dioctyl-1,7-dibromo-3,4,9,10-perylenetetracarboxylic acid diimide, the preparation process is as follows:

[0058]

[0059] Under nitrogen protection, add 1mmol n-octylamine to 15mL propionic acid solution containing 0.1mmol 1,7-dibromo-3,4,9,10-perylene dianhydride, reflux overnight; after the reaction, cool to room temperature , the reaction solution was poured into an aqueous sodium hydroxide solution, extracted with chloroform, the organic phase was collected and the organic solvent was removed, the solid was washed with ethyl acetate and then dissolved in chloroform, the obtained solution was subjected to column chromatography on aluminum peroxide, and aft...

Embodiment 2

[0066] Example 2: Dithiophene-pyrrolo[3,4-c]pyrrole diketope-N,N'-di(1-octylnonyl)-substituted-3,4,9,10-perylenetetracarboxylic acid of this example The diimide copolymer has the following structural formula:

[0067]

[0068] The preparation process of above-mentioned polymer is as follows:

[0069] The synthesis of N,N'-bis(1-octylnonyl)-1,7-dibromo-3,4,9,10-perylenetetracarboxylic acid diimide, the preparation process is as follows:

[0070]

[0071] Under nitrogen protection, 1mmol (1-octylnonylamine) was added to 15 mL of propionic acid solution containing 0.1 mmol 1,7-dibromo-3,4,9,10-perylenedianhydride, and refluxed overnight. After the reaction, cool to room temperature, pour the reaction solution into an aqueous sodium hydroxide solution, extract with chloroform, collect the organic phase and remove the organic solvent, wash the solid with ethyl acetate and dissolve it in chloroform, and perform column chromatography on aluminum peroxide , The solvent was r...

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Abstract

The invention relates to a copolymer containing diketopyrrolopyrrole and perylene diimide, and the compolymer comprises the structural formula shown in the specification. In the structural formula, n is a natural number between 1 to 100, R1 is C1-C20 alkyl or a structure shown in the specification, and in the R1 structure, R2, R3 and R4 are H, C1-C20 alkyl or C1-C20 alkyloxy, and R5, R6 and R7 are H or C1-C20 alkyl. The copolymer consisting of diketopyrrolopyrrole and perylene diimide can form an extremely strong donor-acceptor structure, thereby helping to improving the material stability on the one hand, and helping to reduce the material band gap on the other hand, so that the light absorption scope of the material is enlarged, and the photoelectric converting efficiency is improved. Additionally, the invention also relates to a preparation method and application of the copolymer.

Description

technical field [0001] The invention relates to the field of organic semiconductor materials, in particular to a copolymer containing diketopyrrolopyrrole and perylene tetracarboxylic acid diimide, 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 to that of commer...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D519/00C09K11/06H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕李满园
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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