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Perylenetetracarboxylic diimide copolymer containing thiophenepyrrole dione unit, preparation method thereof and application thereof

A technology of perylene tetracarboxylic acid diimide and pyrrole diketone, which is applied in the field of organic compound synthesis, can solve the problems of reducing the photoelectric conversion efficiency of organic solar cells, unable to use sunlight effectively, and the emission spectrum matching degree is not enough, etc. The effect of excellent charge transport performance, high yield, and excellent solubility

Inactive Publication Date: 2012-02-08
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0003] Perylenetetracarboxylic acid diimide and its derivatives contain a large planar conjugated system and good molecular coplanarity. The interaction of large π bonds between molecules is very strong and has a large lattice energy, so its solubility Poor, poor film-forming processing performance, resulting in the preparation of the device is prone to phase separation, affecting the efficiency of exciton diffusion, resulting in energy loss
In addition, since the absorption spectrum of perylenetetracarboxylic diimide and its derivatives is mainly concentrated in the visible region, the absorption range is not wide enough, and the matching degree with the emission spectrum of sunlight is not high enough, so the sunlight cannot be effectively used, and the will reduce the photoelectric conversion efficiency of organic solar cells

Method used

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  • Perylenetetracarboxylic diimide copolymer containing thiophenepyrrole dione unit, preparation method thereof and application thereof
  • Perylenetetracarboxylic diimide copolymer containing thiophenepyrrole dione unit, preparation method thereof and application thereof
  • Perylenetetracarboxylic diimide copolymer containing thiophenepyrrole dione unit, preparation method thereof and application thereof

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preparation example Construction

[0032] The present invention also provides a method for preparing the perylenetetracarboxylic diimide copolymer containing thienopyrrole diketopyrrole units, which comprises the following steps:

[0033] Step S1, respectively provide the compound I represented by the following structural formula 1 , I 2 ,

[0034]

[0035] Among them, R 1 , R 2 , R 3 selected from -H, C 1 ~C 20 Alkyl, C 1 ~C 20 Alkoxybenzene or phenyl; R 4 , R 5 from C 1 ~C 20 the alkyl group; R 6 from C 1 ~C 20 Alkyl or alkoxy;

[0036] Step S2, in an oxygen-free environment, in a system containing the first catalyst and the first organic solvent, compound I 1 , I 2 Carry out Stille coupling reaction, generate the described thienopyrrole diketone unit perylenetetracarboxylic diimide copolymer containing the following formula compound I,

[0037]

[0038] In the formula, n is an integer between 1 and 200.

[0039] The chemical reaction formula of the above-mentioned Stille coupling react...

Embodiment 1

[0065] Poly N,N'-bis-(3,4,5-tri-methylbenzene)-3,4,9,10-perylenediimide-5-methyl-1,3-bis(thiophene-2 -yl)-4H-thiophene[3,4-c]pyrrole-4,6(5H)-dione (n=11):

[0066] 1. Preparation of N, N'-two-(3,4,5-tri-methylbenzene)-1,7-dibromo-3,4,9,10-perylenediimide

[0067]

[0068] Weigh 0.27mmol 1,7-dibromo-3,4,9,10-perylene tetraanhydride in a reaction flask, add 0.84mmol 3,4,5-tri-methyl-1-aminobenzene and 12ml propionic acid , placed in an ultrasonic device for ultrasonication for 20 minutes, then heated to 80°C after 30 minutes of nitrogen gas, reacted for 48 hours, then cooled to room temperature, added chloroform to dissolve, and washed the organic layer with sodium bicarbonate solution to obtain The red suspension was filtered, dried by adding anhydrous magnesium sulfate, and spin-dried. The product was obtained after column separation (dichloromethane:petroleum ether=3:1). MS (EI) m / z: 784 (M+)

[0069] 2. Preparation of 5-methyl-1,3-bis(5-thiophen-2-yl)-4H-thiophene[3,4...

Embodiment 2

[0082] 1. N, N'-bis-(3,4,5-tri-methoxybenzene)-1,7-dibromo-3,4,9,10-perylenediimide and 5-octyl- For the preparation of 1,3-bis(5-tributyltinthiophen-2-yl)-4H-thiophene[3,4-c]pyrrole-4,6(5H)-dione, refer to Example 1;

[0083] 2. Poly N, N'-bis-(3,4,5-tri-methoxybenzene)-3,4,9,10-perylene diimide-5-octyl-1,3-bis( Preparation of thiophen-2-yl)-4H-thiophene[3,4-c]pyrrole-4,6(5H)-dione (n=14):

[0084]

[0085] Under the protection of argon, to the compound N,N'-bis-(3,4,5-tri-methoxybenzene)-1,7-dibromo-3,4,9,10-perylenediimide Amine 0.5mmol, 5-octyl-1,3-bis(5-tributyltinthiophen-2-yl)-4H-thiophene[3,4-c]pyrrole-4,6(5H)-dione 0.5mmol Dioxane (15 mL) solution. Introduce argon, bubble 0.5h to remove residual oxygen. Then add Pd(PPh 3 ) 2 Cl 2 10mg, continue to feed argon, bubble 0.5h to remove residual oxygen, and then heat to 85°C for 36 hours. The mixture was added dropwise to methanol for settling. Suction filtration, washing with methanol, and drying. It was then...

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Abstract

The invention discloses a perylenetetracarboxylic diimide copolymer containing a thiophenepyrrole dione unit, a preparation method thereof and an application thereof. The molecular structure of the copolymer is represented by general formula (I); and in the formula (I), n is an integer between 1 and 200, R1, R2, and R3 are selected from hydrogen, C1-C20 alkyl, C1-C20 alkyloxyphenyl, or phenyl, R4and R5 are selected from C1-C20 alkyl, and R6 is selected from C1-C20 alkyl or alkyloxy. The perylenetetracarboxylic diimide copolymer containing the thiophenepyrrole dione unit of the invention has the advantages of good solvability, high carrier mobility, strong absorbance, wide light absorption range, and improvement of the sunlight utilization rate; and the preparation method has the advantages of simple process, high yield, and easy operation and control.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a perylenetetracarboxylic diimide copolymer containing a thienopyrrole diketone unit 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 clos...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46H01L51/54C09K11/06H01L51/30
CPCH01L51/0053Y02E10/549H10K85/621
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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