Polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, preparation method and application thereof

A technology of benzothiadiazole and dithiophene, which is applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, organic chemistry, etc., can solve the problem that the absorption spectrum cannot be well matched with the solar spectrum, the energy transfer efficiency is low, and the problems such as low energy conversion efficiency, to achieve the effect of expanding the light absorption range, improving the carrier mobility, and reducing the band gap

Active Publication Date: 2014-06-11
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 ca

Method used

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  • Polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, preparation method and application thereof
  • Polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, preparation method and application thereof
  • Polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0066] P1:

[0067] The preparation method includes the following steps:

[0068] 1. The preparation method of compound A1 includes 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, which is 2-bromophenylnaphthalene; provide compound b, which is 2,6-dibromocyclopenta[2,1-b;3,4-b’]dithiophen-4-one;

[0072] Under the protection of nitrogen, add 1.42g (5mmol) of compound a to 60mL of anhydrous tetrahydrofuran, cool to -78°C, slowly add 3mL of n-butyllithium in n-hexane solution (2.5mol / L, 7.5mmol), and complete the addition. After stirring and reacting at -78°C for 1h, slowly add dropwise the solution obtained by dissolving 1.83g (5mmol) of compound b and 15ml of dry THF, returning to room temperature, and cont...

Embodiment 2

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

[0091] P2:

[0092] The preparation method includes the following steps:

[0093] 1. The preparation method of compound A2 includes 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, which is 2-bromophenylnaphthalene; provide compound b, which is 2,6-dibromocyclopenta[2,1-b;3,4-b’]dithiophen-4-one;

[0097] Under the protection of nitrogen, add 1.42g (5mmol) of compound a to 60mL of anhydrous tetrahydrofuran, cool to -78°C, slowly add 2.4mL of n-butyllithium in n-hexane solution (2.5mol / L, 6mmol), and complete the addition. After stirring and reacting at -78°C for 1h, slowly add dropwise the solution obtained by dissolving 2.2g (6mmol) of compound b and 20ml of dry THF, returning to room temperature, and cont...

Embodiment 3

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

[0116] P3:

[0117] The preparation method includes the following steps:

[0118] 1. The preparation method of compound A3 includes 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, which is 2-bromophenylnaphthalene; provide compound b, which is 2,6-dibromocyclopenta[2,1-b;3,4-b’]dithiophen-4-one;

[0122] Under the protection of nitrogen, add 1.42g (5mmol) of compound a to 60mL of anhydrous tetrahydrofuran, cool to -78℃, slowly add 2.8mL of n-butyllithium in n-hexane solution (2.5mol / L, 7mmol), and the addition is complete After stirring and reacting at -78°C for 1h, slowly add dropwise the solution obtained by dissolving 2.0g (5.5mmol) of compound b in 20ml of dry tetrahydrofuran, returning to room tempera...

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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 optoelectronic materials, in particular to a polymer containing thienothiophene, benzothiadiazole and cyclopentadithiophene, and a preparation method and application thereof. Background technique [0002] Organic solar cells have some advantages that inorganic solar cells can't match, such as low cost, simple manufacturing process, light product weight, and large-area flexible preparation. Therefore, they have received extensive attention as a potential renewable energy source. In the past ten years, the performance of organic solar cells has been steadily improved, and the energy conversion efficiency has approached 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 th...

Claims

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Application Information

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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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