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Cyclopentadiene dithiophene-thiarolobis(benzothiadiazole) copolymer and its preparation method and application

A technology of cyclopentadiene dithiophene and benzothiadiazole, which is applied in the field of cyclopentadiene dithiophene-thiarolodipolymer and its preparation, can solve the problems of low energy conversion efficiency, spectral response load, and mobility low level problem

Active Publication Date: 2016-01-13
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although people have invested a lot of research on polymer solar cells and achieved rapid development, the energy conversion efficiency of polymer solar cells is still lower than that of silicon solar cells. One of the reasons is that the carrier mobility ratio of polymers is relatively high. Inorganic single crystal materials have orders of magnitude lower mobility
The spectral response of the currently used conjugated polymer photovoltaic materials is relatively poor, and its absorption spectrum cannot match the solar spectrum well, which is another important reason for the low energy transfer efficiency.

Method used

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  • Cyclopentadiene dithiophene-thiarolobis(benzothiadiazole) copolymer and its preparation method and application
  • Cyclopentadiene dithiophene-thiarolobis(benzothiadiazole) copolymer and its preparation method and application
  • Cyclopentadiene dithiophene-thiarolobis(benzothiadiazole) copolymer and its preparation method and application

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preparation example Construction

[0055] see figure 1 , the preparation method of the cyclopentadiene dithiophene-thiarolo two (benzothiadiazole) copolymer of one embodiment, comprises the steps:

[0056] Step S110: preparing compound A and compound B.

[0057] The structural formula of compound A is:

[0058]

[0059] Among them, R 1 and R 2 for C 1 ~C 20 the alkyl group; R 1 and R 2 Can be the same or different; R 1 and R 2 It is straight chain alkyl or branched chain alkyl.

[0060] Compound A was prepared using Compound C and Compound D as reactants. Wherein, the structural formula of compound C is:

[0061]

[0062] The structural formula of compound D is:

[0063]

[0064] Among them, R 1 and R 2 for C 1 ~C 20 the alkyl group; R 1 and R 2 Can be the same or different; R 1 and R 2 It is straight chain alkyl or branched chain alkyl.

[0065] In an inert gas (nitrogen, helium, argon, etc.) protective atmosphere, compound C was dissolved in the first solvent to obtain the first ...

Embodiment 1

[0109] Preparation of poly{4,4-dioctyl-cyclopentadieno[2,1-b;3,4-b']dithiophene-6,6dioctylthirolo[3,2-e:4 ,5-e] two (benzothiadiazole)}, the structural formula is:

[0110]

[0111] 1. Preparation of compound C—4,4’-dibromo-6,6’-diiodo-bi-2,1,3-benzothiadiazole

[0112] (1) Preparation of 5-nitro-2,1,3 benzothiadiazole

[0113] Add 2-amino-5-nitroaniline (22.95g, 0.15mol) and 100ml thionyl chloride (SOCl 2 ), stirred and slowly added 2ml of pyridine dropwise, heated and refluxed at 80-90°C for 24h, stopped the reaction, heated to 80°C and rotary evaporated excess SOCl 2 Afterwards, the reaction product was cooled to room temperature, poured into a large amount of water, stirred, filtered, washed with water and then vacuum-dried to obtain 21.7 g of the product 5-nitro-2,1,3-benzothiadiazole with a yield of 80%.

[0114] The reaction formula is as follows:

[0115]

[0116] (2) Preparation of 4,7-dibromo-5-nitro-2,1,3 benzothiadiazole

[0117] Add 5-nitro-2,1,3 benzot...

Embodiment 2

[0142] Preparation of poly{{4,4-bis(n-eicosyl)-cyclopentadieno[2,1-b; 3,4-b']dithiophene-6,6 dimethylthiarolo[3 ,2-e:4,5-e] two (benzothiadiazole)}, the structural formula is:

[0143]

[0144] 1. Preparation of compound C—4,4’-dibromo-6,6’-diiodo-bi-2,1,3-benzothiadiazole

[0145] The preparation method is the same as in Example 1.

[0146] 2. Preparation of compound A—4,8-dibromo-6,6-dimethylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)

[0147] Add 4,4'-dibromo-6,6'-diiodo-bi2,1,3 benzothiadiazole (compound C) (3.4g, 5mmol) and 50ml THF into a three-necked flask, and stir for 20min with nitrogen gas , slowly add n-butyllithium (4mL, 2.5M, 0.01mol) dropwise for half an hour, control the temperature at -90°C, keep stirring at -90°C for 2 hours, add 4.73ml of dimethyl dichloride Silane (compound D) (10 mmol), raised to room temperature, stirred for 10 hours. Stop the reaction, wash with water, extract with anhydrous ether, obtain an organic layer, dry over anhydrous sodium...

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Abstract

The invention provides a cyclopentadiene dithiophene-silolobis(diazosulfide) copolymer. The molecular general formula is shown in the specification, wherein R1, R2, R3 and R4 are C1-C20 alkyl groups, and n is an integer ranging from 1 to 100. The cyclopentadiene dithiophene-silolobis(diazosulfide) copolymer has relatively high carrier mobility and relatively wide spectral response. Furthermore, the invention also provides a preparation method and application of the cyclopentadiene dithiophene-silolobis(diazosulfide) copolymer.

Description

technical field [0001] The invention relates to the field of optoelectronic materials, in particular to a cyclopentadienedithiophene-thiarolobis(benzothiadiazole) copolymer and its preparation method and application. Background technique [0002] The preparation of low-cost and high-efficiency solar cells has always been a research hotspot and difficulty in the field of photovoltaics. Due to the complex production process and high cost of commercialized silicon solar cells, their applications are limited. 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. [0003] Polymer solar cells have excellent market prospects due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating and printing. Although people have invested a lot of research on polymer solar cells and achieved rapid development, the energy conversio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD