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Preparation and application of oligomer photovoltaic donor material based on 5,6-difluorobenzothiadiazole unit

A photovoltaic material and oligomer technology, which is applied in the synthesis and application field of A'2DA' type oligomer donor material, can solve the problem that the relationship between photovoltaic performance is not clear, and achieves high yield, wide light absorption range, high The effect of open circuit voltage

Inactive Publication Date: 2020-04-21
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few literature reports on oligomer photovoltaic materials based on D-A block units, and the relationship between the molecular structure and photovoltaic performance of oligomer photovoltaic materials based on D-A block units is not yet clear.

Method used

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  • Preparation and application of oligomer photovoltaic donor material based on 5,6-difluorobenzothiadiazole unit
  • Preparation and application of oligomer photovoltaic donor material based on 5,6-difluorobenzothiadiazole unit
  • Preparation and application of oligomer photovoltaic donor material based on 5,6-difluorobenzothiadiazole unit

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The synthesis route of A'-D-A-D-A' type organic small molecule donor material SM1 is as follows:

[0055]

[0056] 1.1 Synthesis of compound 3

[0057] Under nitrogen protection, compound 1 (6.0 g, 12.40 mmol), compound 2 (1.63 g, 4.94 mmol), Pd(PPh 3 ) 4 (0.29 g, 5% mol) and 48 mL toluene, 110 o C was refluxed for 3 h, stopped the reaction, extracted with dichloromethane, combined the organic phases, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered with suction, and spin-dried the solvent. The crude product was purified by column chromatography using petroleum ether as the eluent. 2.38 g of orange-yellow solid compound 3 was isolated with a yield of 86%. 1 H NMR (400 MHz, CDCl 3 ) δ 8.09 (s, 2H), 7.19 (s, 2H), 2.66 (d, J = 6.9 Hz, 4H), 1.65-1.60 (m,2H), 1.40 - 1.25 (m, 16H), 0.94-0.90 (m, 12H).

[0058] 1.2 Synthesis of compound 4

[0059] In a 100 mL single-necked flask, compound 3 (2.3 g, 4.10 mmol), N-bromosuccinimide (1.68 g,...

Embodiment 2

[0067] A'(D-A) 2 The synthetic route of DA'-type oligomer donor material SM2 is as follows:

[0068]

[0069] 2.1 Synthesis of Compound 7

[0070] Under nitrogen protection, (5-(1,3-dioxolan-2-yl)thiophen-2-yl)tributyltin (2.48 g, 5.57 mmol), compound 4 (4.0 g, 5.57 mmol), Pd (PPh 3 ) 4 (0.32 g, 5% mol) and 70 mL toluene, 110 o C was refluxed for 12 h, stopped the reaction, cooled to room temperature, and distilled off the toluene solvent under reduced pressure. The remaining crude product was dissolved in 35 mL of tetrahydrofuran, added aqueous hydrochloric acid (10%, 20 mL), and stirred overnight at room temperature. Transfer the reaction solution to a separatory funnel, extract with dichloromethane, combine the organic phases, wash with saturated brine, dry over anhydrous magnesium sulfate, filter with suction, and spin to dry the solvent. The crude product is separated into petroleum ether: dichloromethane ( V: V , 1: 1) as the eluent, separated by column chromat...

Embodiment 3

[0076] Photophysical, electrochemical and thermodynamic stability tests of the small molecule SM1 synthesized in Example 1.

[0077] The thermogravimetric curve of small molecule SM1 is as follows: figure 1 As shown, its decomposition temperature is 393 o c.

[0078] The UV-Vis absorption spectra of small molecule SM1 in chloroform solution and solid film such as figure 2 shown. Exhibits strong absorption at 300-650 nm. The absorption peak around 330 nm is the π-π* transition absorption peak of the molecule, and the absorption peak at 547 nm can be attributed to the charge transfer from the donor unit thiophene to the acceptor unit benzothiadiazole and terminal cyano-rhodanine (ICT ) transition absorption peak. Compared with the absorption spectrum of the solution, the absorption peak of the solid film of small molecule SM1 has a red shift and an absorption shoulder peak, which is caused by the accumulation of molecules in the solid film. The measured peak position is ...

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Abstract

The invention relates to preparation and application of an oligomer photovoltaic donor material which is based on a 5,6-difluorobenzothiadiazole unit and has an A'(D-A)2DA' framework. The electron donating (D) unit is thiophene, bithiophene, benzodithiophene and derivatives thereof, the electron accepting (A) unit is 5,6-difluorobenzothiadiazole and derivatives thereof, and the electron accepting(A') unit is cyano-rhodanine, cyano-indandione and derivatives thereof. The oligomer has good film-forming property, high light absorption coefficient, wide light absorption range and proper energy level. Compared with a solar cell made of an A'-D-A-D-A' type small molecular photovoltaic material, the solar cell made of the A'(D-A)2DA' type oligomer shows better photovoltaic performance, and the energy conversion efficiency of a device is improved by nearly 20%.

Description

technical field [0001] The invention relates to the field of organic photovoltaic materials, in particular to a class of A'(D-A) 2 Synthesis and application of DA'-type oligomer donor materials. Background technique [0002] With the increasing consumption of energy, organic solar cells (OSCs) have attracted much attention as a clean energy conversion method. It has the advantages of low cost, light weight, wide source, easy adjustment of molecular structure, and large-area flexible device preparation, etc., and has attracted extensive attention from researchers around the world. [1] . After three decades of unremitting efforts, the current photoelectric conversion efficiency (PCE) of OSCs has exceeded 13% in single-layer devices. [2-5] , the efficiency of stacked devices has exceeded 17% [6] . [0003] In terms of active layer donor materials for organic solar cells, oligomer materials (Oligomer Materials, OMs) photovoltaic materials have excellent film-forming propert...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D417/14C07F7/08H01L51/42H01L51/46
CPCC07D519/00C07D417/14C07F7/0816H10K85/6576H10K85/40H10K30/00Y02E10/549
Inventor 顾子倩郭佳莉郝儒林马超范燕凯邓晓媛钱宇朱卫国
Owner CHANGZHOU UNIV
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