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Perylene tetracarboxylic diimide-carbazole-dithienyldiazosulfide conjugated polymer as well as preparation method and application thereof

A perylenetetracarboxylic acid diimide and conjugated polymer technology, which is applied in the field of organic compound synthesis, can solve problems such as low carrier mobility, low conversion efficiency, and ineffective use of carrier electrode collection efficiency. , to achieve the effects of enhancing electron affinity, improving utilization, and being easy to operate and control

Inactive Publication Date: 2011-08-10
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 of polymer solar cells mainly focuses on the donor-acceptor blend system, and the energy conversion efficiency of PCPDTBT and PCBM blend system has reached 6.5% (Jin Young Kim, et al.Science 2007, 317, 222), However, the conversion efficiency is still much lower than that 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, and the high photon flux. The red light region is not effectively utilized and the electrode collection efficiency of carriers is low.

Method used

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  • Perylene tetracarboxylic diimide-carbazole-dithienyldiazosulfide conjugated polymer as well as preparation method and application thereof
  • Perylene tetracarboxylic diimide-carbazole-dithienyldiazosulfide conjugated polymer as well as preparation method and application thereof
  • Perylene tetracarboxylic diimide-carbazole-dithienyldiazosulfide conjugated polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of N,N'-two-(3,4,5-tri-dodecyloxybenzene)-1,7-dibromo-3,4,9,10-perylenediimide:

[0040]

[0041] In the reaction flask, add 0.192g 1,7-dibromo-3,4,9,10-perylene tetraanhydride, 0.70g 3,4,5-tri-dodecyloxy-1-aminobenzene and 16ml propane acid, ultrasonically oscillated for 10 minutes to fully mix the reactants, and then pass nitrogen gas into the reactants for 0.5 hours, then stop feeding nitrogen gas, and heat the reactants to 80° C. for 48 hours. After the reaction was completed, cool to room temperature, add chloroform to dissolve, then wash the organic layer with sodium bicarbonate solution to obtain a red suspension, filter, add anhydrous magnesium sulfate to the filtrate to dry to remove water, and finally spin dry. The product was obtained after column separation (dichloromethane:petroleum ether=3:1). MS (EI) m / z: 1806 (M+).

Embodiment 2

[0043] Preparation of 5-tributylstannane-3-hexylthiophene:

[0044]

[0045] Add 5mL 3-hexylthiophene and 50mL THF to a 250mL three-necked flask, then cool down to -30°C with liquid nitrogen / isopropanol, then add 2.5M n-butyllithium dropwise, and react at -30°C for 1 hour, then Join SnBu at one time 3 Cl (96%) 8.5mL, continued to react at -30°C for 0.5 hours, then naturally warmed up to room temperature, and allowed the reaction system to continue to react for 45 hours, then moved the mixture containing the reaction product into ice water, added and extracted with diethyl ether, Finally, dry over anhydrous magnesium sulfate to remove water, remove the solvent under reduced pressure, and use silica gel / petroleum ether (30-60° C.) column chromatography to obtain a colorless and transparent oily liquid.

Embodiment 3

[0047] Preparation of 4,7-bis(3-hexylthiophene)-2,1,3-benzothiadiazole:

[0048]

[0049] Add 1mol of 4,7-dibromo-2,1,3-benzothiadiazole and 2mol of 5-tributylstannane-3-hexylthiophene, 0.03mol of PdCl to a 250mL three-necked flask 2 (PPh 3 ) 2 , 30ml of THF, after reflux reaction under nitrogen protection for 6 hours, then remove the solvent under reduced pressure to obtain a red solid, and then apply the obtained red solid to silica gel / CH 2 Cl 2 / petroleum ether (60-90° C., volume ratio 1:1) column chromatography, and then the column chromatography product was recrystallized with absolute ethanol to obtain orange-red needle-like crystals. MS (EI) m / z: 468 (M+).

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Abstract

The invention discloses a perylene tetracarboxylic diimide-carbazole-dithienyldiazosulfide conjugated polymer the general formula of which is shown in a formula (I) as well as a preparation method and application thereof. The preparation method comprises the following steps: using 1,7-dibromo-3,4,9,10-perylene tetracarboxylic dianhydride and 3,4,5-trialkoxy-1-aminobenzene to react, thus obtaining a monomer; and under an oxygen-free condition, using the monomer, 4,7-dithienyl-2,1,3-diazosulfide dibromine and N-alkyl-carbazole diborate to perform polymerization reaction, thus obtaining the target product. The preparation method is simple, is easy to operate and control and is suitable for industrial production. The target product prepared by the method has good solubility; and when being used in the field of organic solar cells, the target product has high absorbance and wide absorption range which can extend to the near infrared region, thus the solar energy utilization rate of the product can be increased.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a perylenetetracarboxylic acid diimide-carbazole-bithienylbenzothiadiazole conjugated polymer 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 c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/00H10K99/00
CPCH01L51/0053Y02E10/549Y02P70/50H10K85/621
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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