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Tetracarboxylic acid diimide copolymer containing cyclopentadienedithiophene unit, its preparation method and its application

A perylene tetracarboxylic acid diimide copolymer and a technology containing cyclopentadiene dithiophene are applied in the field of organic compound synthesis and can solve the mismatch between the spectral response of the device and the solar radiation spectrum, the ineffective use of the red light region, Problems such as low collection efficiency of carrier electrodes, to achieve the effects of wide light absorption range, increased carrier mobility, easy operation and control

Inactive Publication Date: 2013-01-16
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 on polymer solar cells is mainly focused on the donor-acceptor blend system. The energy conversion efficiency of PCPDTBT and PCBM blend system has reached 6.5%, but it is still much lower than the conversion efficiency of inorganic solar cells. The main constraints to 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 red region of high photon flux is not effectively utilized, and the electrode of the carrier low collection efficiency

Method used

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  • Tetracarboxylic acid diimide copolymer containing cyclopentadienedithiophene unit, its preparation method and its application
  • Tetracarboxylic acid diimide copolymer containing cyclopentadienedithiophene unit, its preparation method and its application
  • Tetracarboxylic acid diimide copolymer containing cyclopentadienedithiophene unit, its preparation method and its application

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preparation example Construction

[0032] Further, the embodiment of the present invention also provides a method for preparing the perylene tetracarboxylic diimide copolymer containing cyclopentadiene dithiophene unit, comprising 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 from C 1 ~C 20 alkyl;

[0035] (2) Under the condition that there is catalyst and organic solvent in the anaerobic environment, compound A, B are carried out Stille coupling reaction, obtain following structural general formula and be that the cyclopentadiene dithiophene unit perylene tetracarboxylate represented by (I) Acid diimide 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 this t...

Embodiment 1

[0050] Poly N, N'-bis-(3,4,5-tri-methylbenzene)-3,4,9,10-perylenediimide-(4,4-di-hexyl)cyclopentadiene ( 2,1-b:3,4-b')dithiophene I 1 The preparation, its chemical reaction formula is as follows:

[0051]

[0052] Set up reaction apparatus, go to containing compound N, N'-bis-(3,4,5-tri-methylbenzene)-1,7-dibromo-3,4,9,10-perylene diimide 0.5mmol , 4,4-di-hexyl-2,6-bistributyltin-cyclopentadiene (2,1-b:3,4-b') in DMF (18mL) solution of 0.5mmol of dithiophene was bubbled for 0.5 hours , to remove the oxygen in the reaction environment, and then add Pd 2 (dba) 3 (0.014g, 0.015mol) and P(o-Tol) 3 (0.0083g, 0.027mmol), followed by bubbling for 0.5 hours to remove residual oxygen in the environment, and then heating 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 solution ...

Embodiment 2

[0054] Poly N,N'-bis-(3,4,5-tri-methoxybenzene)-3,4,9,10-perylenediimide-(4,4-di-octyl)cyclopentadiene Alkene(2,1-b:3,4-b')dithiophene 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, 4,4-di-octyl-2,6-bistributyltin-cyclopentadiene (2,1-b:3,4-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. 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 solution of sodium diethyldithiocarbamate, and th...

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Abstract

The invention discloses, as shown in a general formula (I), a tetracarboxylic acid diimide copolymer containing a cyclopentadienedithiophene unit, a preparation method and an application, in the formula, n is an integer between 1-100; R1, R2, R3 are selected from hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy benzene group or a phenyl group; R4 is selected from the C1-C20 alkyl group. The copolymer of the invention has the advantages of good dissolvability, strong absorbancy and wide absorption scope, and is capable of extending to a near infrared zone, the copolymer of the invention has excellent charge transmission performance and increases the utilization rate of sunlight. The preparation method is simple, and is easy to operate and control, the tetracarboxylic acid diimide copolymer is 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 cyclopentadiene dithiophene 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 cl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/00H01S5/36H10K99/00
CPCH01L51/0053Y02E10/549H10K85/621
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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