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Bithiophene benzobithiophene conjugated polymer material and preparation method and application thereof

A compound and reaction technology are applied to dithienobenzodithiophene conjugated polymer materials and the fields of their preparation and application, which can solve the problems of increasing social operating costs, environmental pollution and the like, and achieve the effect of high photoelectric conversion efficiency

Active Publication Date: 2015-06-10
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This not only leads to the increase of the operating cost of the whole society, but also brings serious environmental pollution problems.

Method used

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  • Bithiophene benzobithiophene conjugated polymer material and preparation method and application thereof
  • Bithiophene benzobithiophene conjugated polymer material and preparation method and application thereof
  • Bithiophene benzobithiophene conjugated polymer material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、2

[0070] Example 1, 2,6-bis(trimethyltin base)-4,8-bis(5-(2-ethylhexyl)thiophen-2 base)-dithieno[2,3-d:2' , 3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDT-T) synthesis

[0071]chemical reaction flow chart Figure 13 Shown, concrete reaction steps and reaction conditions are as follows:

[0072] Preparation of compound 7: 5,10-bis(2-ethyl-hexyloxy)dithiophene[2,3-d:2′,3′-d′]-benzo[2,3-d:2 ', 3'-d'] dithiophene (compound 6, 1.2g, 2mmol) (preparation of compound 6 cited literature Y.Wu, Z.J.Li, X.Guo, H.L Fan, L.J.Huo, J.H.Hou, J.Mater. Chem.2012, 22, 21362-21365) was dissolved in 50 mL of acetone, and 20 mL of an aqueous solution of cerium amine nitrate (6 mmol, 3.3 g) was added dropwise at room temperature. After the dropwise addition was completed, the mixture was stirred at room temperature for 1 hour. The reaction mixture was slowly poured into 100 mL of deionized water, and the precipitated solid was filtered and vacuum-dried for 1 day to obtain 0.5 g of red solid powder wit...

Embodiment 2

[0077] Example 2, poly{[4,8-bis((2-ethyl-hexyl)thienyl)-dithieno[2,3-d:2',3'-d']benzo[1,2 -b: Synthesis of 4,,5-b']dithiophene]-co[thienyl[3,4-b]thiophen-2yl-]-2-hexylnonyl-1-one} (polymer P3)

[0078] chemical reaction flow chart Figure 16 Shown, concrete reaction steps and reaction conditions are as follows:

[0079] Take the monomer 2,6-bis(trimethyltinyl)-4,8-bis((2-ethyl-hexyl)thienyl)-dithieno[2,3-d:2′,3′- d′]benzo[1,2-b:4,,5-b′]dithiophene (DTBDT-T) (0.288 g, 0.25 mmol) and the monomer 2,5-dibromo-thienyl[3,4 -b] thiophen-2 base-]-2-hexylnonyl-1-one (TTC, 0.205g, 0.25mmol), after it was dissolved in a mixed solvent of toluene (8mL) and DMF (2mL), the The air was evacuated for 5 minutes, and the catalyst tetrakis(triphenylphosphine)palladium(0) (20 mg) was added, followed by further evacuation of the air for 25 minutes. Polymerization was then stopped after 16 hours at the reflux temperature of toluene. The polymer solution was cooled to room temperature, slowly po...

Embodiment 3

[0080] Example 3, poly{[4,8-bis((2-ethyl-hexyl)thienyl)-dithieno[2,3-d:2',3'-d']benzo[1,2 -b: Synthesis of 4,,5-b']dithiophene]-co[thienyl[3,4-b]thiophen-2yl-]-2-hexyldecyl-1-ester} (polymer P1)

[0081] chemical reaction flow chart Figure 14 Shown, concrete reaction steps and reaction conditions are as follows:

[0082] Take the monomer 2,6-bis(trimethyltinyl)-4,8-bis((2-ethyl-hexyl)thienyl)-dithieno[2,3-d:2′,3′- d′]benzo[1,2-b:4,,5-b′]dithiophene (DTBDT-T) (0.288 g, 0.25 mmol) and the monomer 2,5-dibromo-thienyl[3,4 -b] thiophen-2-yl-]-2-hexylnonyl-1-ester (TTE, 0.215g, 0.25mmol), after it was dissolved in a mixed solvent of toluene (8mL) and DMF (2mL), the The air was evacuated for 5 minutes, and the catalyst tetrakis(triphenylphosphine)palladium(0) (20 mg) was added, followed by further evacuation of the air for 25 minutes. Polymerization was then stopped after 16 hours at the reflux temperature of toluene. The polymer solution was cooled to room temperature, slowly ...

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Abstract

The invention discloses a bithiophene benzobithiophene conjugated polymer material and a preparation method and an application thereof. The polymer material has the structural formula shown in the formula I in the specification, wherein R1 represents linear or branched alkyl with the carbon atom number from 4 to 20; R2 represents linear or branched alkyl with the hydrogen atom number or the carbon atom number from 4 to 20; R3 and R4 are selected from any one of the following groups: hydrogen, linear or branched alkyl, alkoxy, sulfuryl, subsulfuryl, ester group and carbonyl which are not substituted or are substituted by halogens and have the hydrogen and carbon atom number from 1 to 30, cyan, nitro, aryl, aralkyl, halogen, and aryl which is substituted by a substituent containing single bond, double bond, triple bond or combination thereof; m represents the number of the repeated units of thiophene in the polymer and is a natural number between 0 and 3; and n represents the number of the repeated units of the polymer and is a natural number between 5 and 1000. The polymer material disclosed by the invention can be applied to the photoelectric field such as organic solar cells and the field of field-effect tubes with high migration.

Description

technical field [0001] The invention relates to a dithienobenzodithiophene conjugated polymer material, a preparation method thereof and an application in optoelectronics. Background technique [0002] With the rapid development of society and economy, the demand and usage of fossil energy are increasing rapidly. This not only leads to the increase of the operating cost of the whole society, but also brings serious environmental pollution problems. For example, the rapid increase in the number of automobiles directly leads to the rapid consumption of traditional fossil energy such as gasoline and natural gas, and the exhaust emissions lead to serious environmental pollution, which directly or indirectly restricts the sustainable development of our modern society. Therefore, it has become our consensus to develop green and renewable energy as soon as possible. As an important part of clean and renewable energy, solar cells have made great progress in recent years. Solar ce...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D519/00C07D495/22C08L65/00H01L51/46
CPCY02E10/549
Inventor 霍利军侯剑辉
Owner INST OF CHEM CHINESE ACAD OF SCI