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4,8-Diisooctyloxyphenyl[1,2-b:4,5-b']bithiophene and fluoroquinoxaline conjugated polymer

A technology of isooctyloxyphenyl and fluoroquinoxaline is applied in the application field of preparing polymer photovoltaic cells and achieves the effects of excellent performance and symmetrical structure

Inactive Publication Date: 2014-10-15
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the research results of researchers in this field, if fluorine atoms are introduced into the electron-deficient unit of quinoxaline to prepare a new type of fluorine-containing D-A-D donor polymer, it is expected to obtain similar properties, but so far there has been no research on this type of material. Preparation method and report on its application in photovoltaic cells

Method used

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  • 4,8-Diisooctyloxyphenyl[1,2-b:4,5-b']bithiophene and fluoroquinoxaline conjugated polymer
  • 4,8-Diisooctyloxyphenyl[1,2-b:4,5-b']bithiophene and fluoroquinoxaline conjugated polymer
  • 4,8-Diisooctyloxyphenyl[1,2-b:4,5-b']bithiophene and fluoroquinoxaline conjugated polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Polymer A

[0039] Step 1. Preparation of 6-fluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline

[0040] The synthetic route is as follows:

[0041]

[0042] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine

[0043] 5-Fluoro-4,7-dibromo-2,1,3-benzothiadiazole (5g, 0.016mol) was dissolved in 150ml absolute ethanol, NaBH was added in batches at 0℃ 4 (11.1g, 0.29mol), then react at room temperature for 20h; after the reaction, concentrate to remove ethanol, add 160ml of water, extract with ethyl acetate, wash the organic phase with saturated brine, and finally use anhydrous MgSO 4 Drying; concentration to remove the organic solvent, the crude product obtained is purified by silica gel column chromatography, the eluent is n-hexane / ethyl acetate (the volume ratio of n-hexane to ethyl acetate is 25:1) to obtain 4-fluoro- 3.5 g of 3,6-dibromo-1,2-phenylenediamine, with a yield of 78%.

[0044] (2) Preparation of 1,2-bis(3-octyloxyphenyl)ethanedione

[0045] Li...

Embodiment 2

[0061] Example 2: Polymer B

[0062] The synthetic route is as follows:

[0063]

[0064] In this example, 6,7-difluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline was used as the electricity-deficient unit, and the polymerization in step 3 of Example 1 was used. The method prepared polymer B with a yield of 85%, a number average molecular weight of 58563, and a molecular weight distribution of 1.96. Among them, the preparation method of 6,7-difluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline adopts the method in step 1 of Example 1, the difference is that it uses 4,5-difluoro-3,6-dibromo-1,2-phenylenediamine instead of 4-fluoro-3,6-dibromo-1,2-phenylenediamine, 6,7-difluoro The NMR characterization data of -5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline are: 1 HNMR(CDCl 3 ,500MHz,ppm),δ=7.32(m,4H),7.24(t,2H),6.98(m,2H),3.95(t,4H)1.76(m,4H),1.45(dd,4H),1.34 (m, 16H), 0.93 (t, 6H).

[0065] Electrochemical test: use CHI660D electrochemical workstation, use glassy carb...

Embodiment 3

[0067] Example 3: Polymer C

[0068] The synthetic route is as follows:

[0069]

[0070] In this example, 6-fluoro-5,8-dibromo-2,3-bis(4-octyloxyphenyl)quinoxaline was used as the electricity-deficient unit, and polymer C was prepared by the method in step 3 of Example 1 , The yield is 85%, the number average molecular weight is 45315, and the molecular weight distribution is 2.11.

[0071] Electrochemical test: use CHI660D electrochemical workstation, use glassy carbon electrode as working electrode, platinum wire electrode as counter electrode, Ag / Ag + The electrode is a reference electrode, Bu 4 N·PF 6 As an electrolyte, the HOMO energy of polymer C film measured by cyclic voltammetry in acetonitrile solvent is -5.20 eV, which is lower than -5.16 eV of non-fluorinated material B', which is 0.04 eV, see Table 1.

[0072] Photovoltaic performance research: using ITO / PEDOT:PSS / polymer:PC 61 BM / LiF / Al sandwich battery structure, combining polymer C and acceptor material PC 61 BM is ma...

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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-diisooctyl alkoxy phenyl [1, 2-b; 3, 4-b] bithiophene and fluoro-quinoxaline. The conjugated polymer is represented as formula I, is prepared by means of Stille coupled reaction of dibromo-fluoro-quinoxaline and 2, 6-bis (trimethyltin)-4, 8-diisooctyl alkoxy phenyl [1, 2-b; 3, 4-b] bithiophene and is used for electron donor materials of polymer bulk heterojunction photovoltaic cells. Fluorine atoms with strong electron withdrawing groups are introduced onto quinoxaline of an electron-deficient unit of the polymer, so that the HOMO (highest occupied molecular orbital) energy level of the materials can be effectively reduced, and further, open-circuit voltage of polymer photovoltaic cells is increased.

Description

Technical field [0001] The invention belongs to the field of functional polymers, and specifically relates to a conjugated polymerization of 4,8-diisooctyloxyphenyl [1,2-b:4,5-b']bithiophene and fluoroquinoxaline And its application for preparing polymer photovoltaic cells. Background technique [0002] With economic development and population growth, the energy crisis is intensifying, and the development of renewable new energy has become more and more urgent. [0003] As an inexhaustible green energy source, solar energy has received extensive attention from the international community for its utilization and development. Polymer solar cells have become a research hotspot at home and abroad in recent years due to their simple preparation process, low cost, light weight, and flexible devices. The current focus of polymer solar cell research is the development of highly efficient conjugated polymers. Body and acceptor materials to improve its photoelectric energy conversion effic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 高潮武海梅王维平田地刘红利安忠维王户生
Owner XIAN MODERN CHEM RES INST