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Conjugated polymer of 4,8-di(5-isooctyl thiophene)phenyl [1,2-b; 3,4-b]bithiophene and chloroquinoxaline

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

Inactive Publication Date: 2012-12-19
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 above theory and other similar studies, it is expected to obtain similar properties by introducing fluorine atoms into the electron-deficient unit of quinoxaline to prepare a new type of fluorine-containing D-A-D donor polymer, but so far there is no preparation method for this type of material and its application in photovoltaic cells

Method used

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  • Conjugated polymer of 4,8-di(5-isooctyl thiophene)phenyl [1,2-b; 3,4-b]bithiophene and chloroquinoxaline
  • Conjugated polymer of 4,8-di(5-isooctyl thiophene)phenyl [1,2-b; 3,4-b]bithiophene and chloroquinoxaline
  • Conjugated polymer of 4,8-di(5-isooctyl thiophene)phenyl [1,2-b; 3,4-b]bithiophene and chloroquinoxaline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Polymer A

[0039] Step 1, preparing 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline The synthetic route is as follows:

[0040]

[0041] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine

[0042]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), and then reacted at room temperature for 20; 4 Drying; the crude product obtained after concentrating to remove the organic solvent was purified by silica gel column chromatography with the eluent n-hexane / ethyl acetate (the volume ratio of n-hexane and ethyl acetate was 25:1) to obtain 4-fluoro-3,6 -Dibromo-1,2-phenylenediamine 3.5g, yield 78%.

[0043] (2) Preparation of 1,2-bis(3-octyloxyphenyl)ethanedione

[0044] Add LiBr (5.25g, 60.4mmol) to a THF solution (40ml) of CuBr (4.33g, 30.2mmol), stir and dissolve at room temperature, drop the temperature to 0°C...

Embodiment 2

[0063] Example 2: Polymer B

[0064] The synthetic route is as follows:

[0065]

[0066] 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 same polymerization method as in Step 3 of Example 1, with a yield of 65%, a number average molecular weight of 23129, and a molecular weight distribution of 1.88.

[0067] 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 film was measured by cyclic voltammetry to be -5.33eV, which is 0.14eV lower than -5.19eV of the non-fluorinated material A', see Table 1.

[0068] Photovoltaic performance research: using ITO / PEDOT:PSS / polymer:PC 61 The sandwich cell structure of BM / LiF / Al...

Embodiment 3

[0069] Example 3: Polymer C

[0070] The synthetic route is as follows:

[0071]

[0072] In this example, 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(4-octyloxyphenyl)quinoxaline is used as the electro-deficient unit, and Example 1 Polymer C was synthesized by the method in step 3, the yield was 72%, the number average molecular weight was 34752, and the molecular weight distribution was 2.34.

[0073] The method in Step 1 of Example 1 was used to prepare 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(4-octyloxyphenyl)quinoxaline.

[0074] 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 -5.23eV, which is 0.08eV lower than -5.15eV of the non-fluorinated material B', se...

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Abstract

The invention belongs to the functional polymer material field, and concretely relates to a conjugated polymer of 4,8-di(5-isooctyl thiophene)phenyl [1,2-b; 3,4-b]bithiophene and chloroquinoxaline, a structural general formula of the conjugated polymer is shown as I. The polymer is prepared by a Stille coupling reaction of dibromo chloroquinoxaline and 2,6-di(trimethyl)-4,8-di(5- isooctyl thiophene)phenyl [1,2-b; 3,4-b]bithiophene, and is used for an electron donor material of a polymer heterojunction photovoltaic cell. The polymer introduces a strong electron-withdrawing group fluorine atom on an electron-deficient unit, thereby the HOMO energy level of the material can be effectively reduced, thereby the open-circuit voltage of the polymer photovoltaic cell can be enhanced.

Description

technical field [0001] The invention belongs to the field of functional polymers, in particular to a co-polymer of 4,8-bis(5-isooctylthiophene)phenyl[1,2-b;3,4-b]bithiophene and fluoroquinoxaline Conjugated polymers and their use for the preparation of polymer photovoltaic cells. Background technique [0002] With the development of social economy and population growth, the ensuing energy problems are becoming more and more serious, and the development of renewable new energy is imminent. As an inexhaustible green energy, how to develop and effectively utilize solar energy has attracted widespread attention from the international community. A device that converts solar energy into electrical energy - polymer solar cells, has become a research hotspot at home and abroad in recent years due to its outstanding advantages such as simple preparation process, low cost, light weight and flexible devices, and the current research focus of polymer solar cells It is the development ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
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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