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Conjugated polymer of 4,8-diisooctane alkoxy phenyl [1,2-b;3,4-b] bithiophene and fluorinated quinoxaline

A kind of technology of isooctyloxyphenyl and fluoroquinoxaline, applied in the field of functional polymers

Inactive Publication Date: 2012-12-26
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Therefore, the introduction of fluorine atoms on the electron-deficient unit of quinoxaline to prepare a new type of fluorine-containing D-A-D donor polymer is expected to obtain similar properties, but so far there is no preparation method for this type of material and its application in photovoltaic cells. report

Method used

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  • Conjugated polymer of 4,8-diisooctane alkoxy phenyl [1,2-b;3,4-b] bithiophene and fluorinated quinoxaline
  • Conjugated polymer of 4,8-diisooctane alkoxy phenyl [1,2-b;3,4-b] bithiophene and fluorinated quinoxaline
  • Conjugated polymer of 4,8-diisooctane alkoxy phenyl [1,2-b;3,4-b] bithiophene and fluorinated quinoxaline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: Polymer A

[0042] Step 1, preparing 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline The synthetic route is as follows:

[0043]

[0044] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine

[0045] 5-Fluoro-4,7-dibromo-2,1,3-benzothiadiazole (5g, 0.016mol) was dissolved in 150ml of absolute ethanol, and NaBH was added in batches at 0°C 4 (11.1g, 0.29mol), then reacted at room temperature for 20h; after the reaction was over, distilled off ethanol under reduced pressure, added 160ml of water, extracted with ethyl acetate, washed the organic phase with saturated brine, and finally anhydrous MgSO 4The crude product obtained after drying and concentrating to remove the organic solvent was chromatographed on a silica gel column with n-hexane / ethyl acetate (the volume ratio of n-hexane to ethyl acetate was 25:1) to obtain 4-fluoro-3,6-dibromo- 1,2-phenylenediamine 3.5g, yield 78%;

[0046] (2) Preparation of 1,2-bis(3...

Embodiment 2

[0068] Example 2: Polymer B

[0069] The synthetic route is as follows:

[0070]

[0071] In this embodiment, 6,7-difluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline is used as the deficient unit. Polymer B was prepared by the method of Step 3 in Example 1, with a yield of 88.9%, a number average molecular weight of 24513, and a molecular weight distribution of 2.05.

[0072] Electrochemical test: use CHI660D electrochemical workstation, use glassy carbon electrode as working electrode, platinum wire electrode as counter electrode, Ag / Ag + The electrode is the reference electrode, Bu 4 N·PF 6 As an electrolyte, in acetonitrile solvent, the HOMO energy of the polymer B thin film was determined by cyclic voltammetry to be -5.26eV, which is 0.1eV lower than -5.16eV of the corresponding material A' without fluorination, see Table 1.

[0073] Photovoltaic performance research: using ITO / PEDOT:PSS / polymer:PC 61 The sandwich battery structure of BM...

Embodiment 3

[0074] Example 3: Polymer C

[0075]The synthetic route is as follows:

[0076]

[0077] In this example, 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(4-octyloxyphenyl)quinoxaline is used as the defect unit, and the steps in Example 1 are adopted Polymer C was prepared by the method in the third method, the yield was 58.4%, the number average molecular weight was 36875, and the molecular weight distribution was 2.33.

[0078] Prepare 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(4-octyloxyphenyl)quinoxaline by the method in Step 1 of Example 1;

[0079] Electrochemical test: use CHI660D electrochemical workstation, use glassy carbon electrode as working electrode, platinum wire electrode as counter electrode, Ag / Ag + The electrode is the reference electrode, Bu 4 N·PF 6 As an electrolyte, in acetonitrile solvent, the HOMO energy of the polymer C thin film was measured by cyclic voltammetry to be -5.21eV, which is 0.06eV lower than -5.15eV of the corresponding...

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Abstract

The invention belongs to the field of functional polymer materials, and particularly relates to a conjugated polymer of 4,8-diisooctane alkoxy phenyl [1,2-b;3,4-b] bithiophene and fluorinated quinoxaline, the structural formula of which is shown by I. The polymer is prepared by the Stille coupling reaction of double bromide fluorinated quinoxaline and a 2,6-bis(trimethyltin)-4,8-diisooctane alkoxy phenyl [1,2-b;3,4-b] bithiophene reagent and is used for electron donor materials of polymer bulk heterojunction photovoltaic cells. The polymer disclosed by the invention introduces strong electron-withdrawing fluorine atom to the electron-deficient unit quinoxaline, thus effectively reducing the HOMO energy level of materials and enhancing the open circuit voltage of polymer solar cells.

Description

technical field [0001] The invention belongs to the field of functional polymers, in particular to conjugated polymers of 4,8-diisooctyloxyphenyl[1,2-b; 3,4-b]bithiophene and fluoroquinoxaline and their Applications for the preparation of polymer photovoltaic cells. Background technique [0002] Facing the rapid development of the global economy and the growth of the population, the ensuing energy demand is also increasing day by day. The development of renewable new energy is an effective way to solve the current energy crisis. [0003] Solar energy is an inexhaustible green energy, and its utilization and development have drawn extensive attention from the international community. As a device that converts solar energy into electrical energy, polymer solar cells have become a research hotspot at home and abroad in recent years. The current focus of this type of battery research is to develop efficient conjugated polymer donor and acceptor materials to improve their photo...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 高潮武海梅王维平田地丛志远安忠维弥育华
Owner XIAN MODERN CHEM RES INST
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