A kind of organic solar cell electron acceptor material and its preparation method and application

A technology for electron acceptor materials and solar cells, applied in organic chemistry, electrical solid-state devices, semiconductor/solid-state device manufacturing, etc., to achieve the effects of simple regulation, easy purification, and simple synthesis

Active Publication Date: 2020-04-24
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nevertheless, its efficiency still has a large gap (20%) from commercialization, and how to improve its performance is still the core issue of its development

Method used

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  • A kind of organic solar cell electron acceptor material and its preparation method and application
  • A kind of organic solar cell electron acceptor material and its preparation method and application
  • A kind of organic solar cell electron acceptor material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the synthesis of BTTCN

[0041] When terminal group A is selected from group A1, reaction scheme 1:

[0042]

[0043]Synthetic procedure for preparing BTTCN intermediate BrRTCN: Add malononitrile (52.3 mg, 0.79 mmol) and BrRTCHO (200 mg, 0.66 mmol) into 20 mL of chloroform. Then 0.1 mL of triethylamine was added and stirred at room temperature for 10 minutes. The reaction was quenched with ice water, then extracted and washed three times with dichloromethane and water respectively, dried over anhydrous magnesium sulfate, filtered and concentrated. Purify by column chromatography using a mixed solvent of petroleum ether and dichloromethane to obtain BrRTCN (211.5 mg, 91.3%). 1 H NMR (400MHz, CDCl 3 ):δ7.71(s,1H),7.38(s,1H),2.54-2.53(d,2H),1.61-1.58(m,1H),1.32-1.24(m,8H),0.90-0.86(m ,6H). 13 C NMR (100MHz, CDCl 3 ): δ150.17, 143.93, 139.56, 134.75, 124.64, 113.78, 113.03, 39.85, 33.37, 32.38, 28.71, 25.58, 22.98, 14.10, 10.75, 0.97. MALDI-TOF-MS(m / z...

Embodiment 2

[0046] Embodiment 2: the synthesis of BTTIC:

[0047] When terminal group A is selected from group A8, reaction scheme 2:

[0048]

[0049] Intermediates for the preparation of BTTIC:

[0050] Synthetic steps of BrRTIC: BrRTCHO (200mg, 0.66mmol) and (3-oxo-2,3-dihydro-1H-inden-1-ylidene) malononitrile (154.2mg, 0.79mmol) were added to 20mL chloroform middle. Then add 0.1 mL of triethylamine and stir at room temperature for one hour. The reaction was quenched with ice water, then extracted and washed three times with dichloromethane and water respectively, dried over anhydrous magnesium sulfate, filtered and concentrated. Purify by column chromatography using a mixed solvent of petroleum ether and dichloromethane to obtain BrRTIC (256.9 mg, 81.2%). 1 H NMR (400MHz, CDCl 3 ):δ7.71(s,1H),7.69(s,3H),7.68(t,3H),7.52(s,3H),7.33(t,3H),7.38(s,1H),2.54-2.53( d,2H),1.61-1.58(m,1H),1.32-1.24(m,8H),0.90-0.86(m,6H). 13 C NMR (100MHz, CDCl 3 ):δ161.61,161.01,159.53,158.31, 157.66...

Embodiment 3

[0053] Embodiment 3: Apply the product BTTCN in Embodiment 1 to an organic photovoltaic device, and its device construction method and its performance parameters are as follows:

[0054] Device 1: The target product BTTCN in Example 1 was blended with the commercial polymer donor material PTB7-Th, using chloroform as the solvent, and the device structure was prepared as ITO / ZnO / PTB7-th:BTTCN(1:1.5) / MoO 3 / Ag organic photovoltaic devices, the thickness of the active layer is about 90nm.

[0055] Device 2: Combine the target product BTTCN in Example 1 with commercialized PTB7-Th and fullerene electron acceptor material PC 71 BM blending, with chlorobenzene / 1,8-diiodooctane as solvent, the device structure is ITO / ZnO / PTB7-th:PC 71 BM:BTTCN(1:1.5:0.03) / MoO 3 / Ag organic photovoltaic devices, the thickness of the active layer is about 100nm.

[0056] Reference device preparation: the commercial polymer donor material PTB7-Th and PC 71 BM blending, with chlorobenzene / 1,8-diiod...

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Abstract

The invention discloses an electron acceptor material for an organic solar cell and its preparation method and application. Using benzotrithiophene core, introducing different numbers of thiophene unit bridges, and then introducing strong electron-withdrawing groups at the end to realize its photoelectric properties regulation to construct high-performance electron acceptor materials for organic solar cells. The organic solar cell electron acceptor material of the present invention exhibits excellent exciton separation ability, has good thermal stability, electrical stability and solution processing performance, and is easy to synthesize, easy to purify, and low in cost. It is a fullerene electron acceptor material. potential substitutes. It is suitable as a non-fullerene electron acceptor material and widely used in the preparation of high-performance organic solar cell devices.

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials and applications, and in particular relates to an organic optoelectronic material, more specifically an electron acceptor material for an organic solar cell and its preparation method and application. Background technique [0002] Organic solar cells are a new type of thin-film solar cell technology that converts light into electricity. Compared with traditional silicon-based photovoltaic cells, it has the advantages of low cost, light weight, less environmental pollution, and easy realization of large area and flexibility. It has become one of the research hotspots in academia and industry in recent years. After nearly ten years of rapid development, its photoelectric conversion efficiency has exceeded 14%. Nevertheless, its efficiency still has a large gap (20%) from commercialization, and how to improve its performance is still the core issue of its development. [0003] At p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/14H01L51/46
CPCC07D495/14H10K85/655H10K85/654H10K85/6576Y02E10/549Y02P70/50
Inventor 赖文勇汪洋徐巍栋黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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