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Perylenetetracarboxylic acid diimide copolymer containing benzothiophene unit and preparation method and application thereof

A technology of perylene tetracarboxylic acid diimide copolymer and perylene tetracarboxylic acid diimide, which is applied in the direction of electrical components, semiconductor/solid-state device manufacturing, electric solid-state devices, etc., can solve the problem of not effectively utilizing carriers Electrode collection efficiency, low conversion efficiency, low carrier mobility, etc., to achieve the effects of easy operation and control, wide absorption range, and improved solubility

Inactive Publication Date: 2011-11-30
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 constraints that limit the performance improvement are: the relatively low carrier mobility of organic semiconductor devices, the spectral response of the device does not match the solar radiation spectrum, the high photon flux The amount of red light is not effectively utilized and the electrode collection efficiency of carriers is low.

Method used

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  • Perylenetetracarboxylic acid diimide copolymer containing benzothiophene unit and preparation method and application thereof
  • Perylenetetracarboxylic acid diimide copolymer containing benzothiophene unit and preparation method and application thereof
  • Perylenetetracarboxylic acid diimide copolymer containing benzothiophene unit and preparation method and application thereof

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preparation example Construction

[0032] Further, the embodiment of the present invention also provides a method for preparing the perylenetetracarboxylic diimide copolymer containing benzothiophene units, including the following steps:

[0033] (1) Provide compounds A and B represented by the following structural formula respectively,

[0034] Among them, R 1 , R 2 , R 3 selected from the same or different hydrogen, C 1 ~C 20 Alkyl, C 1 ~C 20 Alkoxybenzene or phenyl; R 4 , R 5 from C 1 ~C 12 Alkyl, C 1 ~C 20 alkoxy;

[0035] (2) In an oxygen-free environment and under the condition that a catalyst and an organic solvent exist, compound A and B are carried out to a Stille coupling reaction to obtain the following general structural formula as (I) containing benzothiophene unit perylenetetracarboxylic acid diacyl imine copolymer,

[0036]

[0037] In the formula, n is an integer between 1 and 100.

[0038] In the above step (1), compound B can be prepared according to conventional methods in...

Embodiment 1

[0050] Poly N,N'-bis-(3,4,5-tri-methylbenzene)-3,4,9,10-perylenediimide-2,6-(4,8-di-hexyloxy ) Benzo[1,2-b:4,5-b']dithiophene copolymer I 1 The preparation, its chemical reaction formula is as follows: (no preparation example of compound A?)

[0051]

[0052] Set up a reaction device to contain the compound N, N'-bis-(3,4,5-tri-methylbenzene)-1,7-dibromo-3,4,9,10-perylene diimide 0.5mmol , 2,6-bistributyltin-(4,8-di-hexyloxy)benzo[1,2-b:4,5-b']dithiophene 0.5mmol DMF (18mL) solution in 0.5 hours, to remove the oxygen in the reaction environment, then add Pd 2 (dba) 3 0.015mol (0.014g) and P (o-Tol) 3 0.027mmol (0.0083g), then continue bubbling for 0.5 hours to remove residual oxygen in the environment, and then heat the reaction system to 80°C for 48 hours. The mixed solution obtained after the reaction is added dropwise to methanol for sedimentation, suction filtered, washed with methanol, dried, and then dissolved in toluene, the solution is added to the aqueous solu...

Embodiment 2

[0054] Poly N,N'-bis-(3,4,5-tri-methoxybenzene)-3,4,9,10-perylenediimide-2,6-(4,8-dioctyloxy ) Benzo[1,2-b:4,5-b']dithiophene copolymer I 2 The preparation, its chemical reaction formula is as follows:

[0055]

[0056] Set up a reaction device to contain the compound N, N'-bis-(3,4,5-tri-methoxybenzene)-1,7-dibromo-3,4,9,10-perylene diimide 0.5 mmol, 2,6-bistributyltin-(4,8-di-octyloxy)benzo[1,2-b:4,5-b']dithiophene 0.5mmol in dioxane (15mL) solution 0.5 hours of bubbling in order to remove the oxygen in the reaction environment, and then add Pd (PPh 3 ) 2 Cl 2 10 mg, then continue to bubble for 0.5 hours to remove residual oxygen in the environment, and then heat the reaction system to 85°C for 36 hours. Add the mixed liquid obtained after the reaction dropwise to methanol for sedimentation, filter with suction, wash with methanol, dry, and then dissolve with toluene, add the dissolved liquid to the aqueous solution of sodium diethyldithiocarbamate, and then heat to...

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Abstract

The invention discloses benzothiophene unit-containing perylene diimide copolymer with the molecular structural general formula (I), and a preparation method and application thereof. In the formula, n is an integer ranging from 1 to 100; R1, R2 and R3 are selected from -H, alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms and phenyl; and R4 and R5 are selected from alkyl with 1 to12 carbon atoms and alkoxy with 1 to 20 carbon atoms. The copolymer has good solubility, high absorbance, wide absorption range capable of extending to a near infrared region, and good charge transfer property, and improves the utilization rate of sunlight; and the preparation method is simple, easy to control and implement, and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a perylene tetracarboxylic diimide copolymer containing benzothiophene units, 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 o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/00H01S5/36H10K99/00
CPCY02E10/549H01L51/0053H10K85/621
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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