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A kind of benzodithiophenedione-benzodithiophene double cable polymer and its preparation and application

A technology of benzodithiophene and benzodithiophene, which is applied in the field of organic semiconductor materials, can solve the problems of limited application, low photoelectric energy conversion efficiency, etc., and achieves good solubility, simple and effective synthesis method, and high absorption range. Effect

Active Publication Date: 2021-06-22
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional double-cable polymer backbones are mainly limited to poly(hexylthiophene) (P3HT), poly(styrene) (MEH-PPV), etc., which limits the application of such materials in single-component organic solar cells.
So far, the photoelectric energy conversion efficiency of single-component polymer solar cells is relatively low, and most of them do not exceed 3%.

Method used

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  • A kind of benzodithiophenedione-benzodithiophene double cable polymer and its preparation and application
  • A kind of benzodithiophenedione-benzodithiophene double cable polymer and its preparation and application
  • A kind of benzodithiophenedione-benzodithiophene double cable polymer and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Synthesis of benzodithiophene dione-benzodithiophene double cable polymer PClBDBNDI:

[0085] The synthetic reaction formula of double-cable polymer PClBDBNDI is as follows:

[0086]

[0087] Concrete synthetic steps are:

[0088] (1) In a 100mL reaction flask, dialkyl bromide substituted benzodithiophene M 1 -1 (225mg, 0.22mmol) and NDI-1 (213mg, 0.49mmol) were dissolved in 30mL DMF, heated to 80°C, and after the dissolution was balanced, potassium carbonate (152mg, 1.10mmol) was added and reacted for 24 hours. After cooling, add Chloroform 50mL, deionized water 200mL, extraction, liquid separation, the organic phase was washed with brine, dried, and the organic solvent was evaporated under reduced pressure to obtain a crude product. Crude product is separated through silica gel column, and eluent dichloromethane:n-hexane=2:1 (v / v), obtains pure M 2 -1, about 90% yield.

[0089] 1 H NMR (400MHz, CDCl 3 ): δ(ppm)8.75(t,8H),7.56(s,2H),7.20(d,2H),6.88(d,2H),4.18(...

Embodiment 2

[0098] Benzodithiophenedione-benzodithiophene double cable polymer PClBDBNDI single-component organic solar cell device:

[0099] The specific device structure of organic solar cells is shown in the attached Figure 10 Shown: Indium tin oxide / zinc oxide (ITO / ZnO) is used as an electrode on a glass substrate, an organic semiconductor active layer is spin-patterned on it, and molybdenum trioxide / silver (MoO 3 / Ag) as the electrode. The thickness of the zinc oxide layer is about 40nm, the thickness of the active layer is about 70nm, the thickness of the molybdenum oxide is about 10nm, and the thickness of the silver is about 80nm.

[0100] The obtained benzodithiophene dione-benzodithiophene type double-cable polymer PClBDBNDI is applied in non-fullerene solar cells as the only active component, with indium tin oxide / zinc oxide (ITO / ZnO) and Molybdenum trioxide / silver (MoO 3 / Ag) as the electrode. The active layer PClBDBNDI was obtained by spin-coating a 10 mg / mL toluene:DIO=...

Embodiment 3

[0103] NDI-2: 1.2g of 1,4,5,8-naphthalenetetracarboxylic anhydride was dissolved in 50mL of DMF solvent, heated to 120°C under nitrogen atmosphere; 1.08g of 2-butyloctylamine was gradually dropped into the reaction solution , react for 6 to 12 hours, use brine and dichloromethane to extract, wash, and dry; dissolve the crude product in 50 mL of acetic acid, and add 2.7 g of ammonium acetate, react at 100 ° C for 3 to 5 hours, use brine and dichloro Methane was extracted, washed, and dried; the crude product was separated through a silica gel column using dichloromethane as a developing solvent to obtain 1.16 g of pure NDI-2. Its NMR spectrum is as Figure 11 shown. According to the synthesis route as in Example 1, the synthesis of the final double-cable polymer was completed.

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Abstract

The invention discloses a benzodithiophenedione-benzodithiophene double-cable polymer and its preparation and application. The double-cable polymer The double-cable polymer connects electron donors and acceptors through covalent bonds to form a single component, which has excellent photoelectric properties and can be used as an organic semiconductor material for single-component organic solar cell materials, organic field materials, etc. Effect transistors, organic light emitting diodes, etc. The synthesis method of the invention is simple and effective, the structure and shape of the double-cable polymer of the invention can be adjusted, and the stability and repeatability are good.

Description

technical field [0001] The invention relates to the technical field of organic semiconductor materials. More specifically, it relates to a benzodithiophenedione-benzodithiophene double cable polymer and its preparation and application. Background technique [0002] Organic solar cells have become a research hotspot in recent years because of their relatively simple preparation process, relatively cheap raw material prices, variability in material design, and the possibility of large-scale preparation. Among them, two-component or multi-component bulk heterojunction solar cells are the most researched, and their energy conversion efficiency has exceeded 17%. However, this type of device has disadvantages such as many optimization steps and poor stability, which is not conducive to the development of organic solar cells. Long-term development. In single-component solar cells, electron donors and acceptors are connected by chemical bonds to form a single-component active laye...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/126C08G2261/91C08G2261/95C08G2261/92C08G2261/124C08G2261/414C08G2261/143C08G2261/145C08G2261/146C08G2261/1412C08G2261/3243C08G2261/3223C08G2261/64C08G2261/512H10K85/113Y02E10/549
Inventor 李韦伟蒋旭东周晟熙
Owner BEIJING UNIV OF CHEM TECH
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