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A thiazolothiazole-dibenzothiophene benzodithiophene polymer and its preparation and application

A technology of dibenzothiophene and benzodithiophene, which is applied in the field of thiazolothiazole-dibenzothiophene benzodithiophene polymer and its preparation, can solve the problem that the absorption spectrum and the solar spectrum cannot be well matched, and the energy Low transfer efficiency, low photoelectric conversion efficiency, etc., to achieve the effect of improving carrier transfer rate, good thermal stability and environmental stability, and easy transfer

Active Publication Date: 2016-03-30
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 thiazolothiazole-dibenzothiophene benzodithiophene polymer and its preparation and application
  • A thiazolothiazole-dibenzothiophene benzodithiophene polymer and its preparation and application
  • A thiazolothiazole-dibenzothiophene benzodithiophene polymer and its preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0065] A thiazolothiazole-dibenzothiophene benzodithiophene polymer, specifically poly{7,8-didecyldibenzo[b,b']thiophenebenzo[2,1-b:3, 4-b']dithiophene-co-2,5-bis(3-octyl-2-thiophene)thiazolo[5,4-d]thiazole} has the following general formula, which is denoted as polymer P1, wherein, n=35:

[0066]

[0067] The preparation method comprises the following steps:

[0068] 1. The reaction to prepare 4,11-dibromo-7,8-diodecyldibenzo[b,b']thiophenebenzo[2,1-b:3,4-b']dithiophene (A1) The route is as follows:

[0069]

[0070] The specific operation is as follows:

[0071] (1) Preparation of 4,5-dicecyl-2,7-trimethyltinbenzo[2,1-b:3,4-b’]dithiophene (b1):

[0072] Add 2.36g (5mmol) 4,5-dicecylbenzo[2,1-b:3,4-b']dithiophene (a1) into 60mL anhydrous tetrahydrofuran in a nitrogen atmosphere and cool to -78°C , slowly add 5mL of n-butyllithium n-hexane solution (2.5M, 12mmol), after the addition is complete, stir and react at -78°C for 2h, add 3.6mL of trimethyltin chloride (12m...

Embodiment 2

[0089] A thiazolothiazole-dibenzothiophene-benzodithiophene polymer, specifically poly{7,8-di(2-ethylpentyl)dibenzo[b,b']thiophenebenzo[2, 1-b:3,4-b']dithiophene-co-2,5-bis(2-thiophene)}, which has the following general formula, is denoted as polymer P2, wherein n=65:

[0090]

[0091] The preparation method comprises the following steps:

[0092] 1. Preparation of 4,11-dibromo-7,8-di(2-ethylpentyl)dibenzo[b,b']thiophenebenzo[2,1-b:3,4-b']di The reaction scheme of thiophene (A2) is as follows:

[0093]

[0094] The specific operation is as follows:

[0095] (1) Preparation of 4,5-bis(2-ethylpentyl)-2,7-bis(trimethyltin)benzo[2,1-b:3,4-b']dithiophene (b2) :

[0096] Add 1.93g (5mmol) of 4,5-bis(2-ethylpentyl)benzo[2,1-b:3,4-b']dithiophene (a2) into 60mL of anhydrous THF under nitrogen atmosphere , cooled to -78°C, slowly added 5mL of n-butyl lithium in n-hexane solution (2.5M, 12mmol), after the addition was completed, stirred and reacted at -78°C for 2h, then added ...

Embodiment 3

[0112] A thiazolothiazole-dibenzothiophene benzodithiophene polymer, specifically poly{dibenzo[b,b']thiophenebenzo[2,1-b:3,4-b']dithiophene -co-2,5-bis(3-octyl-2-thiophene)thiazolo[5,4-d]thiazole has the following general formula, which is denoted as polymer P3, where n=20:

[0113]

[0114] The preparation method comprises the following steps:

[0115] 1. The reaction scheme for preparing 4,11-dibromo-dibenzo[b,b']thiophenebenzo[2,1-b:3,4-b']dithiophene (A3) is as follows:

[0116]

[0117] The specific operation is as follows:

[0118] (1) Preparation of 2,7-bis(trimethyltin)benzo[2,1-b:3,4-b’]dithiophene (b3):

[0119] In a nitrogen atmosphere, add 0.95g (5mmol) benzo[2,1-b:3,4-b']dithiophene (a3) ​​into 60mL anhydrous tetrahydrofuran, cool to -78°C, and slowly add 5mL n-butyl Lithium n-hexane solution (2.5M, 12mmol), after adding, stirred and reacted at -78°C for 2h, then added 3.6mL (12mmol) trimethyltin chloride, kept warm for 0.5h and then returned to room temp...

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Abstract

The present invention provides a polymer containing thiazolothiazole-dibenzothiophene benzodithiophene, a preparation method and an application thereof. The polymer is a polymer P having the following general formula, wherein R1 and R2 are H, C1-C10 alkyl or C1-C10 alkoxy, R3 and R4 are H or C2-C16 alkyl, and n is a natural number of 5-65. According to the present invention, the polymer contains the new dibenzothiophene benzodithiophene and thiazolothiazole unit, has the new conjugate plane structure, 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 thiazolothiazole-dibenzothiophene-benzodithiophene and its preparation method and application. 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 of polymers ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D519/00H01L51/46H01L51/54H01L51/30
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