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Exotic atom-substituted benzothiadiazole-based polymer donor material and preparation method and application thereof

A technology of benzothiadiazole and polymer, which is applied in the field of benzothiadiazole-based polymer donor materials and its preparation, can solve the problems of toxic fluorine reagents, cumbersome synthesis steps, and low yield, and achieve spatial structure Optimizing and improving the effect of photoelectric conversion efficiency

Inactive Publication Date: 2017-08-18
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fluorine-substituted polymers usually have cumbersome synthesis steps, low yields, and the use of very toxic fluorine reagents, which may limit their large-scale applications (M.L.Tang and Z.Bao, Chem.Mater., Halogenated Materials as Organic Semiconductors. 2011, 23, 446.)

Method used

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  • Exotic atom-substituted benzothiadiazole-based polymer donor material and preparation method and application thereof
  • Exotic atom-substituted benzothiadiazole-based polymer donor material and preparation method and application thereof
  • Exotic atom-substituted benzothiadiazole-based polymer donor material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] In this example, the polymer PCBT4T-2OD was prepared by the following method:

[0107] (1) 5-chloro-4,7-bis(5-bromo-4-(2-octyldodecyl)-2-thiophene)-2,1,3-benzothiadiazole (CBT2T-2OD )Synthesis.

[0108]

[0109] ①5-Chloro[2,1,3]benzothiadiazole (2): Add 5-chloro-1,2-o-phenylenediamine (7.83g, 55mmol), pyridine (13.2ml, 165mmol) and chloroform (600ml). Thionyl chloride (8ml, 110mmol) was then added dropwise to the reaction solution at room temperature using a syringe. Subsequently, the reaction was heated to 65 °C and stirred overnight. The reaction was stopped, and after cooling to room temperature, the reactant was quenched by pouring into 200ml of dilute hydrochloric acid, and extracted three times with chloroform. The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and spin-dried, and the residual solid was purified by column chromatography (petroleum ether: dichloromethane, 10:1) to obtain 5.96 g of ...

Embodiment 2

[0122] In this example, polymer PCCBT4T-2OD was prepared by the following method:

[0123] (1) 5,6-dichloro-4,7-bis(5-bromo-4-(2-octyldodecyl)-2-thiophene)-2,1,3-benzothiadiazole ( Synthesis of CCBT2T-2OD).

[0124]

[0125]①5,6-dichloro[2,1,3]benzothiadiazole (6): Add 5,6-dichloro-1,2-o-phenylenediamine (5g , 28.24mmol), pyridine (6.82ml, 84.72mmol) and chloroform (500ml). Thionyl chloride (5.13ml, 70.6mmol) was then added dropwise to the reaction solution at room temperature using a syringe. Then heat up to 65°C under reflux and stir overnight, take a sample on the next day, and stop heating after confirming that the reaction is complete. After cooling to room temperature, pour into 200ml of dilute hydrochloric acid to quench, and extract three times with chloroform. The organic phases were combined, washed three times with saturated brine, dried over anhydrous magnesium sulfate, filtered and spin-dried, and purified by column chromatography (petroleum ether:dichlorome...

Embodiment 3

[0134] In this example, the polymer PCBT4T-2BO was prepared by the following method:

[0135] (1) Synthesis and examples of 5-chloro-4,7-bis(5-bromo-4-(2-hexyldecyl)-2-thiophene)-2,1,3-benzothiadiazole 1 The difference in step (1) is that 2-tributyltin-4-(2-octyldodecyl)thiophene in step ③ is replaced by 2-tributyltin-4-(2-hexyldecyl)thiophene, Thus, 5-chloro-4,7-bis(5-bromo-4-(2-hexyldecyl)-2-thiophene)-2,1,3-benzothiadiazole was prepared.

[0136] (2) The synthesis of 3-cyano-5,5'bis(trimethylstannyl)-2,2'bithiophene is the same as in Example 1.

[0137] (3) Synthesis of polymer PCBT4T-2BO, the chemical reaction formula is as follows:

[0138]

[0139] In a sealed 25ml tube, add 5-chloro-4,7-bis(5-bromo-4-(2-pentyldecyl)-2-thiophene)-2,1,3-benzothiadi Azole (121.3mg, 0.129mmol), 5,5'-bis(trimethyltinthiophene)-2,2'bidithiophene (63.4mg, 0.129mmol), Pd 2 (dba) 3 (4.76mg, 0.0052mmol) and P(o-tol)3 (6.40mg, 0.021mmol). After fully ventilating, 8ml of chlorobenzene was ...

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Abstract

The invention provides an exotic atom-substituted benzothiadiazole-based polymer donor material and a preparation method and application thereof. The exotic atom-substituted benzothiadiazole-based polymer donor material has a structure as shown in a formula I. The polymer donor material has a relatively wide band gap, the band gap is widened along with increase of the content of exotic atoms in a benzothiadiazole unit, and open-circuit voltage Voc of a polymer is increased, thereby achieving the optimal photoelectric energy conversion efficiency of the polymer. The open-circuit voltage of the polymer is also improved by substituting the exotic atoms such as fluorine, chlorine and cyan on bithiophene without current loss, so that the photoelectric conversion efficiency of a solar cell is improved. The high-performance solar cell is achieved by using the polymer as the donor material, the components and the structure of the polymer are optimized through an exotic atom substitution method, the aggregation of donor and acceptor materials and the appearance of a photoelectric device are also optimized, and thus the exotic atom-substituted benzothiadiazole-based polymer donor material has a wide prospect in the aspect of application of a polymer solar cell.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and relates to a heteroatom-substituted benzothiadiazole-based polymer donor material and a preparation method and application thereof. Background technique [0002] In recent years, polymer solar cells (PSCs) due to their low cost, light weight and flexibility (G. Li, V. Shrotriya, J. Huang, Y. Yao, et. al., Nat. Mater., High-efficiency Solution Processable Polymer Photovoltaic Cells by Self-organization of Polymer Blends.2005,4,864; Y.LI,Acc.Chem.Res.,Molecular Design of Photovoltaic Materials for Polymer Solar Cells:Toward Suitable Electronic Energy Levels and Broad Absorption.2011,45.10 Heeger, Adv. Mater., 25th Anniversary Article: Bulk Heterojunction Solar Cells: Understanding the Mechanism of Operation. 2014, 26, 10; L. Lu, T. Zheng, Q. Wu, A. M. Schneider, D. Zhao and L. Yu, Chem .Rev.,Recent advances in bulk heterojunction polymer solar cells.2015,115,12666; Terthiophene-B...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/42H01L51/46
CPCC08G61/123C08G61/126C08G2261/18C08G2261/124C08G2261/1412C08G2261/3246C08G2261/91C08G2261/3223H10K85/151H10K85/113H10K30/50Y02E10/549
Inventor 何凤胡志明陈晖钟筱蔚
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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