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Cross-linkable fluorobenzene-containing end-capped conjugated polymer based on benzodithiophene and double thiophene-substituted difluorobenzothiadiazole and application thereof to solar cell

A technology of difluorobenzothiadiazole and conjugated polymer, which is used in circuits, photovoltaic power generation, electrical components and other directions to achieve the effect of promoting uniform dispersion, wide spectral response range and improving hole and electron transport rate

Inactive Publication Date: 2013-06-19
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are no relevant literature and patent reports at home and abroad to apply conjugated polymers with this structure to solar cells.

Method used

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  • Cross-linkable fluorobenzene-containing end-capped conjugated polymer based on benzodithiophene and double thiophene-substituted difluorobenzothiadiazole and application thereof to solar cell
  • Cross-linkable fluorobenzene-containing end-capped conjugated polymer based on benzodithiophene and double thiophene-substituted difluorobenzothiadiazole and application thereof to solar cell
  • Cross-linkable fluorobenzene-containing end-capped conjugated polymer based on benzodithiophene and double thiophene-substituted difluorobenzothiadiazole and application thereof to solar cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Pentafluorophenyl-terminated poly[4,8-bis(7-octenyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl -5,6-difluoro-4,7-bis(2-thienyl)-2,1,3-benzothiadiazole] alternating copolymer, the implementation steps are as follows.

[0038] Add 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-diketone (2.3 g, 10 mmol), zinc powder (1.5 g, 23 mmol) 35 mL of water, then add 6.4 g of NaOH, stir and heat under reflux for 4 h. Then 8-bromooct-1-ene (6.1 g, 32 mmol) and a small amount of tetrabutylammonium bromide were added to the reaction system and refluxed for 8 h. After the reaction, the reactant was poured into cold water, extracted with ether, and the organic phase was extracted with anhydrous MgSO 4 Concentrate after drying, and then purify with silica gel column to obtain the product 1, [4,8-bis(7-octenyloxy)benzo[1,2-b:4,5-b']dithiophene ].

[0039]

[0040] Under nitrogen atmosphere, 4,8-bis(7-octenyloxy)benzo[1,2-b:4,5-b']dithiophene (0.31 g, 0.9 mmol) was dissolve...

Embodiment 2

[0045] Example 2: Pentafluorophenyl-terminated poly[4,8-bis(6-bromohexyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl The preparation of -5,6-difluoro-4,7-bis(2-thienyl)-2,1,3-benzothiadiazole] alternating copolymer is similar to Example 1, and the implementation steps are as follows.

[0046]

[0047] Add 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-diketone (2.3 g, 10 mmol), zinc powder (1.5 g, 23 mmol) 35 mL of water, then add 6.4 g of NaOH, stir and heat under reflux for 4 h. Then 1,6-dibromo-n-hexane (7.8 g, 32 mmol) and a small amount of tetrabutylammonium bromide were added to the reaction system and refluxed for 8 h. After the reaction, the reactant was poured into cold water, extracted with ether, and the organic phase was extracted with anhydrous MgSO 4 Concentrate after drying, and then purify with silica gel column to obtain 4,8-bis(6-bromohexyloxy)benzo[1,2-b:4,5-b']dithiophene.

[0048] Under nitrogen atmosphere, 4,8-bis(6-bromohexyloxy)benzo[1,2-b:4,5-b']di...

Embodiment 3

[0051] Example 3: Preparation of a polymer solar cell device.

[0052] 10 mg of pentafluorophenyl-terminated poly[4,8-bis(7-octenyloxy)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl-5 ,6-difluoro-4,7-bis(2-thienyl)-2,1,3-benzothiadiazole] mixed with 30 mg PCBM, added 2 mL of chlorobenzene solution, and sprayed on PEDOT by spin coating : A thin film is prepared on the ITO glass modified by PSS, and then the cathode is prepared by vacuum evaporation of lithium fluoride and aluminum.

[0053] The device performance is: standard simulated sunlight (AM 1.5 G, 100 mW / cm 2 ) under irradiation, open circuit voltage = 0.88 V; short circuit current = 13.33 mA / cm 2 ; Fill factor = 65%; Energy conversion efficiency = 7.6%. Its current-voltage curve is attached as figure 2 As shown, the performance stability of the device before and after crosslinking is as follows image 3 shown.

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Abstract

The invention discloses a cross-linkable fluorobenzene-containing end-capped liquid crystal conjugated polymer based on benzodithiophene and double thiophene-substituted difluorobenzothiadiazole and an application thereof to a solar cell. The polymer is characterized by being shown as a structural formula in the specifications. The conjugated polymer disclosed by the invention has liquid crystal characteristic, and can be used for inducing, adjusting and controlling the ordered structure of an active layer and increasing hole mobility; the terminal group of the polymer is functionalized by using a fluorobenzene-containing end-capping agent, so that uniform dispersion between the polymer and PCBM ([6,6]-phenyl-C61-butyric acid methyl ester) can be facilitated, the hole electron transmission rate of the active layer is increased, the device performance is enhanced effectively, and energy transformation efficiency is up to 7.6 percent; and due to the introduction of a cross-linkable unit, a cross-linked active layer material with a stable structure can be obtained, the stability of a device is enhanced, the service life of the device is prolonged, and the efficiency can still reach 7.3 percent 40 days later.

Description

technical field [0001] The invention relates to a crosslinkable fluorine-containing benzene-terminated conjugated polymer based on benzodithiophene and bisthienyl-substituted difluorobenzothiadiazole and its application in solar cells. Background technique [0002] The global energy demand is increasing year by year. As an easy-to-obtain, safe, clean and pollution-free new energy, solar energy provides a new idea for people to solve the energy crisis. Polymer solar cells have become a hot spot in the research and development of solar cells in recent years due to their advantages such as low cost, thin and flexible, easy to realize large-area and flexible devices, and the designability of molecular structures of photovoltaic materials. However, the performance of polymer solar cells is not satisfactory at present. The main reasons are: 1) The band gap of organic semiconductor polymers is too large, and the spectral response range does not match sunlight, which affects the eff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D495/04C07D519/00H01L51/46H01L51/42
CPCY02E10/549
Inventor 陈义旺张琳李璠谌烈
Owner NANCHANG UNIV
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