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Conjugated polymer containing trifluoromethyl, and preparation method and application of conjugated polymer

A conjugated polymer, trifluoromethyl technology, used in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components and other directions, can solve the problems of limiting the open circuit voltage of the device, affecting the device efficiency, improving and other problems, and improving the photoelectric conversion efficiency. Effect

Active Publication Date: 2018-06-22
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, and preparation method and application of conjugated polymer
  • Conjugated polymer containing trifluoromethyl, and preparation method and application of conjugated polymer
  • Conjugated polymer containing trifluoromethyl, and preparation method and application of conjugated polymer

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 invention relates to a conjugated polymer containing trifluoromethyl shown as formula I or II as shown in the specifications; Ar1 and Ar2 are independently selected from a formula as shown in thespecification or a formula as shown in the specification; R1 and R2 are independently selected from hydrogen, alkyl with 1-30 carbon atoms, alkoxyl with 1-30 carbon atoms and alkyl sulphanyl with 1-30carbon atoms; A represents an electron deficiency group and is selected from any one of unsubstituted groups or groups containing substituents: monocyclic arylidene, dicyclic arylidene, arylene containing at least three cycles, monocyclic heteroarylene, dicyclic heteroarylene and heteroarylene containing at least three cycles; the cycles of dicyclic arylene, arylene containing the at least threecycles, dicyclic heteroarylene and heteroarylene containing the at least three cycles are condensed or connected by single bonds; substituents are independent aryl, alkyl with 1-30 carbon atoms, alkoxyl with 1-30 carbon atoms or alkyl sulphanyl with 1-30 carbon atoms; X is selected from N, O S or Se; and n represents the number of repeating units and is a natural number between 1 and 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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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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