A polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene and its preparation and application

A technology of benzothiadiazole and dithiophene, which is applied in the fields of chemical instruments and methods, semiconductor/solid-state device manufacturing, organic chemistry, etc., can solve the problems of poor matching of absorption spectrum and solar spectrum, low energy transfer efficiency, Low energy conversion efficiency and other issues, to achieve the effect of expanding the light absorption range, improving carrier mobility, and reducing the band gap

Active Publication Date: 2016-01-27
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells
[0003] At present, the energy conversion efficiency of organic polymer solar cells is still lower than that of silicon solar cells. One of the reasons is that the carrier mobility of polymers is several orders of magnitude lower than that of inorganic single crystal materials, and the absorption of polymer photovoltaic materials The spectrum does not match well with the solar spectrum, which is another important reason for the low efficiency of energy transfer

Method used

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  • A polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene and its preparation and application
  • A polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene and its preparation and application
  • A polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] A polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, specifically polymer P1 having the following general formula, wherein n=5:

[0066] P1:

[0067] The preparation method comprises the following steps:

[0068] One, the preparation method of compound A1 comprises the following steps:

[0069]

[0070] (1) Preparation of 2,5-dibromo-spiro[cyclopenta[2,1-b;3,4-b’]dithiophene-7,7’-benzofluorene] (d):

[0071] Provide compound a, that is, 2-bromophenylnaphthalene; provide compound b, that is, 2,6-dibromocyclopenta[2,1-b;3,4-b']dithiophen-4-one;

[0072] Under the protection of nitrogen, 1.42g (5mmol) of compound a was added to 60mL of anhydrous tetrahydrofuran, cooled to -78°C, and 3mL of n-butyl lithium in n-hexane solution (2.5mol / L, 7.5mmol) was slowly added, and the addition was completed. , after stirring and reacting at -78°C for 1 h, slowly add dropwise the solution obtained by dissolving 1.83 g (5 mmol) of compound b and 15 ml ...

Embodiment 2

[0090] A polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, specifically a polymer P2 having the following general formula, wherein n=20:

[0091] P2:

[0092] The preparation method comprises the following steps:

[0093] One, the preparation method of compound A2 comprises the following steps:

[0094]

[0095] (1) Preparation of 2,5-dibromo-spiro[cyclopenta[2,1-b;3,4-b’]dithiophene-7,7’-benzofluorene] (d):

[0096] Provide compound a, that is, 2-bromophenylnaphthalene; provide compound b, that is, 2,6-dibromocyclopenta[2,1-b;3,4-b']dithiophen-4-one;

[0097] Under the protection of nitrogen, 1.42g (5mmol) of compound a was added to 60mL of anhydrous tetrahydrofuran, cooled to -78°C, and 2.4mL of n-butyl lithium in n-hexane solution (2.5mol / L, 6mmol) was slowly added, and the addition was completed. , after stirring and reacting at -78°C for 1 h, slowly add dropwise the solution obtained by dissolving 2.2 g (6 mmol) of compound b and 20 m...

Embodiment 3

[0115] A polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, specifically polymer P3 having the following general formula, wherein n=40:

[0116] P3:

[0117] The preparation method comprises the following steps:

[0118] One, the preparation method of compound A3 comprises the following steps:

[0119]

[0120] (1) Preparation of 2,5-dibromo-spiro[cyclopenta[2,1-b;3,4-b’]dithiophene-7,7’-benzofluorene] (d):

[0121] Provide compound a, that is, 2-bromophenylnaphthalene; provide compound b, that is, 2,6-dibromocyclopenta[2,1-b;3,4-b']dithiophen-4-one;

[0122] Under the protection of nitrogen, 1.42g (5mmol) of compound a was added to 60mL of anhydrous tetrahydrofuran, cooled to -78°C, and 2.8mL of n-butyl lithium in n-hexane solution (2.5mol / L, 7mmol) was added slowly, and the addition was completed. , after stirring and reacting at -78°C for 1 h, slowly add dropwise the solution obtained by dissolving 2.0 g (5.5 mmol) of compound b in 20 ml o...

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Abstract

The present invention provides a polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, a preparation method and an application thereof. The polymer is a polymer P having the following general formula, wherein R1 and R2 are the same or different H or C1-C12 alkyl, and n is a natural number of 5-60. According to the present invention, the three units such as thienothiophene, benzothiadiazole and cyclopentadithiophene in the polymer are combined to form the repeated unit having the acceptor-donor-acceptor-donor (A-D-A-D) form so as to enhance the charge transporting in the polymer molecule, reduce the band gap of the polymer, and expand the light absorption range of the polymer material, such that the polymer has characteristics of excellent sunlight matching property, excellent carrier mobility property and simple and controllable preparation method, and has good application prospects in the fields of polymer solar cells, organic electroluminescent devices and other optoelectronic materials. The polymer P is as the follow.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, a preparation method and application thereof. Background technique [0002] Organic solar cells have attracted widespread attention as a potential renewable energy source because of their incomparable advantages over inorganic solar cells, such as low cost, simple manufacturing process, light weight, and large-area flexible preparation. The performance of organic solar cells has steadily improved over the past decade, with energy conversion efficiencies approaching 10%. However, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells. [0003] At present, the energy conversion efficiency of organic polymer solar cells is still lower than that of silicon solar cells. One of the reasons is that the carrier mobility ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D519/00C09K11/06H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕李满园黄佳乐黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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