Thiophene-containing perylene tetracarboxylic diimide copolymer, and preparation method and application thereof

A perylenetetracarboxylic acid diimide and thiophene unit technology, which is applied in the field of organic compound synthesis, can solve the problems of reducing the photoelectric conversion efficiency of organic solar cells, inability to effectively use sunlight, and insufficient matching of emission spectra, and achieve technological Simple, excellent solubility and charge transport properties, and the effect of improving solubility

Inactive Publication Date: 2011-11-09
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
  • Description
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  • Application Information

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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  • Thiophene-containing perylene tetracarboxylic diimide copolymer, and preparation method and application thereof
  • Thiophene-containing perylene tetracarboxylic diimide copolymer, and preparation method and application thereof
  • Thiophene-containing perylene tetracarboxylic diimide copolymer, and preparation method and application thereof

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preparation example Construction

[0036] And, this embodiment also provides the preparation method of the perylene tetracarboxylic diimide copolymer containing thiophene units, comprising the following steps:

[0037] 1.1 respectively provide the compound I represented by the following structural formula 1 , I 2 ,

[0038]

[0039] Among them, R 1 , R 2 , R 3 are the same or different groups selected from -H, C 1 ~C 15 Alkyl, C 1 ~C 15 Alkoxybenzene or phenyl, R 4 , R 5 are the same or different groups selected from C 1 ~C 15 Alkyl, C 1 ~C 15 Alkoxy, C 1 ~C 15 Alkoxybenzene or phenyl, R 6 , R 7 are the same or different -H, or selected from C 1 ~C 15 Alkyl, C 1 ~C 15 Alkoxy, C 1 ~C 15 Alkoxybenzene, phenyl;

[0040] 1.2 In a system containing a catalyst and an organic solvent, compound I 1 , I 2 Carry out Stille coupling reaction, generate the described thiophene unit perylenetetracarboxylic acid diimide copolymer containing thiophene unit of following formula compound I,

[0041]...

Embodiment 1

[0074] Poly N,N'-bis-(3,4,5-tri-dodecyloxybenzene)-3,4,9,10-perylenediimide-5,7-bis(3,6-bis The preparation of octylthieno[3,2-b]thiophene)-thieno[3,4-b]pyrazine, its structural formula is as follows:

[0075]

[0076] Its preparation comprises the following steps:

[0077] 1) Preparation of N, N'-two-(3,4,5-tri-dodecyloxybenzene)-1,7-dibromo-3,4,9,10-perylene diimide, which The reaction is shown in the following formula:

[0078]

[0079] The specific preparation process is: weigh 0.27mmol of 1,7-dibromo-3,4,9,10-perylenetetraanhydride in a reaction flask, add 0.84mmol of 3,4,5-tri-dodecyloxy- 1-Aminobenzene and 12ml of propionic acid were placed in ultrasonic for 10 minutes, then heated to 80°C after 30 minutes of nitrogen gas, and reacted for 48 hours; after the reaction was completed, cooled to room temperature, dissolved in chloroform, and then used Wash the organic layer with sodium bicarbonate solution to obtain a red suspension, filter, add anhydrous magnesium...

Embodiment 2

[0105] Poly N,N'-bis-(3,4,5-tri-octyloxybenzene)-3,4,9,10-perylenediimide-5,7-bis(3,6-dioctyl The preparation of thieno[3,2-b]thiophene)-2,3-dihexylthieno[3,4-b]pyrazine, its structural formula is as follows:

[0106]

[0107] Its preparation comprises the following steps:

[0108] 1) N, N'-bis-(3,4,5-tri-octyloxybenzene)-1,7-dibromo-3,4,9,10-perylene diimide was prepared as in Example 1 Middle (1) step;

[0109] 2) The preparation of 5,7-bis(5-tributyltin-thieno[3,2-b]thiophene))-2,3-dihexylthieno[3,4-b]pyrazine is as in Example 1 (2) to (8) steps;

[0110] 3) Poly N, N'-bis-(3,4,5-tri-octyloxybenzene)-3,4,9,10-perylenediimide-5,7-bis(3,6-di The preparation of octylthieno[3,2-b]thiophene)-2,3-dihexylthieno[3,4-b]pyrazine, its reaction is shown in the following formula:

[0111]

[0112] The specific preparation process is: under the protection of nitrogen, to the compound N, N'-bis-(3,4,5-tri-octyloxybenzene)-1,7-dibromo-3,4,9,10- Perylene diimide 0.5mmol, 5,7-bis...

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Abstract

The invention discloses a thiophene-containing perylene tetracarboxylic diimide copolymer, and a preparation method and application thereof. The thiophene-containing perylene tetracarboxylic diimide copolymer has a general molecular structural formula shown in (I), wherein n is an integer ranging from 1 to 200; R1, R2 and R3, the same or different, are selected from -H, C1-C15 alkyl, and C1-C15 alkoxy benzene or phenyl; R4 and R5, the same or different, are selected from C1-C15 alkyl, C1-C15 alkoxy, and C1-C15 alkoxy benzene or phenyl; and R6 and R7, the same or different, are selected from C1- C15 alkyl, C1-C15 alkyloxy, and C1-C15 alkoxy benzene or phenyl. The thiophene-containing perylene tetracarboxylic diimide copolymer disclosed by the invention has the advantages of high solubility, high carrier mobility, strong absorbance and wide light absorption range, and improves the utilization rate of sunlight. The preparation method of the thiophene-containing perylene tetracarboxylic diimide copolymer is simple in process, high in produce yield, and easy to operate and control.

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 copolymer containing thiophene units and its preparation method and application. 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 c...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D519/00H01L51/30H01L51/46H01L51/54
CPCY02E10/549Y02E10/50H01L51/0053H10K85/621
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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