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Bithiophene pyrrole-silolo-di(benzothiadiazole)-containing copolymer as well as preparation method and application thereof

A technology of benzothiadiazole and dithiophenepyrrole, which is applied in the field of dithiophenepyrrole-thiarolodipolymer and its preparation, can solve the problems of wide energy band gap, lower photon absorption rate, and energy conversion efficiency of organic solar cells low level problem

Active Publication Date: 2014-06-04
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing polymers containing benzothiadiazole units have a wide energy bandgap (the energy level difference between the HOMO energy level and the LUMO energy level), which reduces the absorption rate of photons in the solar spectrum, making it possible to use Organic solar cells with polymers containing benzothiadiazole units have low energy conversion efficiencies

Method used

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  • Bithiophene pyrrole-silolo-di(benzothiadiazole)-containing copolymer as well as preparation method and application thereof
  • Bithiophene pyrrole-silolo-di(benzothiadiazole)-containing copolymer as well as preparation method and application thereof
  • Bithiophene pyrrole-silolo-di(benzothiadiazole)-containing copolymer as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0044] see figure 1 , the preparation method that contains dithiophene pyrrole-thiarolo two (benzothiadiazole) copolymers of one embodiment, comprises the steps:

[0045] Step S110, providing compound A and compound B. The structural formula of compound A is:

[0046]

[0047] Among them, R 1 , R 2 for C 1 ~C 20 the alkyl group;

[0048] The structural formula of compound B is:

[0049]

[0050] Among them, R 3 for C 1 ~C 20 the alkyl group;

[0051] Step S120, in an oxygen-free state, carry out a Stille coupling reaction between Compound A and Compound B at a molar ratio of 1:1.5 to 1.5:1 in an organic solvent containing an organopalladium catalyst, wherein the molar ratio of the catalyst to Compound A is 1 :2000~1:5, after separation and purification, the molecule containing dithiophenepyrrole-thiarolobis(benzothiadiazole) copolymer and dithiophenepyrrole-thiarolobis(benzothiadiazole) copolymer is obtained The general formula is:

[0052]

[0053] Wherein...

Embodiment 1

[0098] This example discloses polymer P1 with the following structure:

[0099]

[0100] The preparation steps of P1 are as follows:

[0101]Step 1. Preparation of 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole

[0102] 1. Preparation of 5-nitro-2,1,3 benzothiadiazole:

[0103]

[0104] Add 2-amino-5-nitroaniline (22.95g, 0.15mol) and 100ml of thionyl chloride into a three-necked flask, stir and slowly add 2ml of pyridine dropwise, heat and reflux at 80~90°C for 24h, stop the reaction , heated to 80°C and rotary evaporated excess SOCl 2 Finally, 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%.

[0105] 2. Preparation of 4,7-dibromo-5-nitro-2,1,3-benzothiadiazole:

[0106]

[0107] Add 5-nitro-2,1,3 benzothiadiazole (10.35g, 60mmol) and 15ml of 40% hydrobromic acid into a three-n...

Embodiment 2

[0128] This example discloses polymer P2 with the following structure:

[0129]

[0130] The preparation steps of P2 are as follows:

[0131] Step 1. Preparation of 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole

[0132] Same as Step 1 of Example 1.

[0133] Step 2, preparation of compound 6,6-dimethyl-4,8-dibromothiarolo[3,2-e:4,5-e]bis(benzothiadiazole):

[0134]

[0135] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole (3.4g, 5mmol), 50ml DMF into a three-necked flask, blow nitrogen into it and stir for 20min, slowly Add n-butyllithium (4mL, 2.5M, 0.01mol) dropwise, drop it in half an hour, control the temperature at -90°C, keep stirring at -90°C for 2 hours, add 4.73ml of dimethyldichlorosilane (10mmol ), raised to room temperature, and stirred for 10 hours. Stop the reaction, wash with water, extract with anhydrous ether, obtain an organic layer, dry over anhydrous sodium sulfate, filter, distill under reduced pressure, and separate by silica gel colum...

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Abstract

The invention relates to a bithiophene pyrrole-silolo-di(benzothiadiazole)-containing copolymer as well as a preparation method and application thereof. The copolymer has a following structural formula (described in the description), wherein n represents an integer of 1-100, and R1, R2, R3 and R4 represent C1-C20 alkyl. The copolymer has a very strong donor- receptor structure which is helpful to improve the stability of the bithiophene pyrrole-silolo-di(benzothiadiazole)-containing copolymer on the other hand and reduce the energy band gap of the bithiophene pyrrole-silolo-di(benzothiadiazole)-containing copolymer, so that the absorption range of the sunlight is extended, and the photoelectric converting efficiency is increased.

Description

technical field [0001] The invention relates to the field of optoelectronic materials, in particular to a pyrrole-thiarolobis(benzothiadiazole) copolymer containing dithiophene and its preparation method and application. Background technique [0002] High-efficiency solar cells are usually made of inorganic semiconductors, but the main silicon solar cells currently on the market are complicated in the production process, serious in pollution, high in energy consumption, and high in cost, which inhibits the development of its commercial application. Therefore, 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. On the one hand, organic semiconductor materials have good environmental stability, low synthesis cost, easy modulation of functions, good flexibility and film-forming properties of organic materials; It has attracted much attention due to its low cost and ot...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07F7/10H01L51/46H01L51/54
CPCY02E10/549
Inventor 周明杰管榕黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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