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

A technology of isooctyloxyphenyl and fluoroquinoxaline, which is applied in the field of functional polymers to achieve the effect of symmetrical structure and excellent performance

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

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Polymer A

[0039] Step 1, the 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 of absolute ethanol, and NaBH was added in batches at 0°C 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 obtained crude product was purified by silica gel column chromatography, and the eluent was n-hexane / ethyl acetate (the volume ratio of n-hexane to ethyl acetate was 25:1) to obtain 4-fluoro- 3.5 g of 3,6-dibromo-1,2-phenylenediamine, yield 78%.

[0044] (2) Preparation of 1,2-bis(3-octyloxyphen...

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 is used as the deficient unit, and the polymerization in Step 3 of Example 1 is adopted Methods Polymer B was prepared with a yield of 85%, a number average molecular weight of 58563, and a molecular weight distribution of 1.96. Wherein 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 4,5-difluoro-3,6-dibromo-1,2-phenylenediamine instead of 4-fluoro-3,6-dibromo-1,2-phenylenediamine, the obtained -5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline NMR data: 1HNMR (CDCl3, 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 carbon electrode as working electrode, p...

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 deficient unit, and the method in Step 3 of Example 1 was used to prepare polymer C , yield 85%, number average molecular weight 45315, molecular weight distribution 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 the reference electrode, Bu 4 N·PF 6 As an electrolyte, in acetonitrile solvent, the HOMO energy of the polymer C film was measured by cyclic voltammetry to be -5.20eV, which is 0.04eV lower than -5.16eV of the non-fluorinated material B', see Table 1.

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

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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, in particular to a conjugated polymer of 4,8-diisooctyloxyphenyl[1,2-b;3,4-b]bithiophene and fluoroquinoxaline and its application in the preparation of polymer photovoltaic cells. Background technique [0002] With the development of the economy and the growth of the population, the energy crisis is getting worse day by day, and the development of renewable new energy is becoming more and more urgent. [0003] As an inexhaustible green energy, solar energy has drawn wide 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 outstanding advantages such as simple preparation process, low cost, light weight and flexible devices. The current research focus on polymer solar cells is to develop efficient conjugated polymers to give Bulk and acceptor materials to improve thei...

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刘红利安忠维王户生
Owner XIAN MODERN CHEM RES INST
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