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Conjugated polymer containing trifluoromethyl group and its preparation method and application

A technology of conjugated polymer and trifluoromethyl, which is applied in the field of trifluoromethyl-containing conjugated polymer and its preparation, can solve the problems of limiting the open circuit voltage of the device, affecting the efficiency of the device, improving the efficiency of the device, and achieving the improvement of photoelectric conversion efficiency effect

Active Publication Date: 2020-05-01
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reduction of the band gap of D-A conjugated polymers is generally accompanied by the increase of the HOMO energy level, which limits the open circuit voltage of the device and affects the further improvement of the device efficiency.

Method used

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  • Conjugated polymer containing trifluoromethyl group and its preparation method and application
  • Conjugated polymer containing trifluoromethyl group and its preparation method and application
  • Conjugated polymer containing trifluoromethyl group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Compound BDTP-m-CF 3 Synthesis

[0055] The reaction scheme is as follows. In the formula, R represents a 2-butyloctane group. The specific reaction steps and reaction conditions are as follows:

[0056]

[0057] (1) Synthesis of compound 2: under argon protection, 4-bromo-2-(trifluoromethyl)phenol (compound 1, 10.85g, 45mmol) and K 2 CO 3 (12.42 g, 90 mmol) was added to 150 mL of DMF. After stirring for 5 minutes, 5-(bromomethyl)undecane (13.46 g, 54 mmol) was added, followed by reaction at 90° C. for 24 hours. The cooled mixture was filtered through a Buchner funnel to remove solids and collect the organic liquid. The organic liquid was extracted three times with ether. The combined organic phases were washed with anhydrous magnesium sulfate (MgSO 4 )dry. After removing the organic solvent, the crude product was purified by a silica gel column and eluted with petroleum ether. Compound 2 shown in the figure was obtained as a pale yellow oil (16.95 g, 92%). ...

Embodiment 2

[0063] Example 2 Polymer PBZ-m-CF 3 Synthesis.

[0064] The chemical reaction scheme of the present embodiment is as follows, and in the formula, R represents 2-butyloctane group, and concrete reaction steps and reaction conditions are as follows:

[0065]

[0066] In a 50 mL double necked round bottom flask, compound BDTP-m-CF 3 (0.3 mmol, 352 mg) and compound FBTZ (0.3 mmol, 210 mg) were dissolved in 10 mL of toluene. After purging with argon for 20 minutes, 18 mg of Pd(PPh 3 ) 4 This was added to the flask as a catalyst, and the reaction mixture was purged with argon for an additional 30 minutes. The reaction mixture was stirred and heated to reflux under an atmosphere of argon for 15 hours. When the reaction mixture was cooled to room temperature, 100 mL of methanol was added to precipitate the polymer, which was collected by filtration, and finally Soxhlet extraction was performed with methanol, n-hexane and chloroform. Polymer recovery from chloroform fractions by...

Embodiment 3

[0074] The polymer PBZ-m-CF prepared by embodiment 2 3 (1.0mg) was dissolved in 1mL of chloroform, and then the solution was added dropwise onto a working electrode, such as a platinum sheet; 0.1mol / L Bu 4 NPF 6 Acetonitrile solution was used as electrolyte; platinum wire was used as counter electrode; silver wire was used as reference electrode. Measured in this system using electrochemical cyclic voltammetry, the polymer PBZ-m-CF 3 The cyclic voltammetry data are shown in image 3 middle. Have image 3 The results can be calculated, the polymer PBZ-m-CF 3 The HOMO energy level of is -5.49eV.

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Abstract

The present invention relates to a conjugated polymer containing trifluoromethyl as shown in formula I or formula II: wherein, Ar 1 and Ar 2 independently selected from or R 1 and R 2 Independently selected from hydrogen, an alkyl group with 1-30 carbon atoms, an alkoxy group with 1-30 carbon atoms, an alkylthio group with 1-30 carbon atoms; A represents an electron-deficient group, which is selected from Any one of the following unsubstituted or substituted groups: monocyclic arylene, bicyclic arylene, arylene containing at least three rings, monocyclic heteroarylene, bicyclic heteroarylene radical, heteroarylene containing at least three rings; bicyclic arylene, arylene containing at least three rings, bicyclic heteroarylene and heteroarylene containing at least three rings in which the rings are fused combined or connected by a single bond; the substituents are independently aryl, an alkyl group with 1-30 carbon atoms, an alkoxy group with 1-30 carbon atoms or an alkylthio group with 1-30 carbon atoms; X is selected from N, O, S or Se; n represents the number of repeating units, and n is a natural number between 1-5000.

Description

technical field [0001] The invention relates to the field of conjugated polymers, in particular to a trifluoromethyl-containing conjugated polymer and its preparation method and application. Background technique [0002] In recent years, organic solar cells, as a new type of thin-film solar cells, have received extensive attention from academia and industry, which consist of blended thin films of conjugated polymer donors and n-type semiconductor acceptors sandwiched between positive and negative electrodes. . Due to its outstanding advantages such as simple preparation process, low cost, light weight, and can be prepared into flexible devices, it has attracted extensive attention. After the design of the material structure, the optimization of the device structure and the processing technology, the photoelectric energy conversion efficiency of the laboratory small-area device based on the blend of the polymer donor material and the n-type non-fullerene acceptor material ha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/123C08G61/126C08G2261/3243C08G2261/414C08G2261/91C08G2261/146C08G2261/1424C08G2261/1412C08G2261/124C08G2261/3223C08G2261/3241C08G2261/18H10K85/151H10K30/00Y02E10/549
Inventor 张茂杰李万宾国霞
Owner SUZHOU UNIV
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