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Electron acceptor material for organic solar cell as well as preparation method and application of electron acceptor material

An electron acceptor material, a technology for solar cells, applied in the fields of organic chemistry, electric solid state devices, semiconductor/solid state device manufacturing, etc., to achieve the effects of low cost, simple synthesis, and simple regulation

Active Publication Date: 2018-11-30
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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  • Electron acceptor material for organic solar cell as well as preparation method and application of electron acceptor material
  • Electron acceptor material for organic solar cell as well as preparation method and application of electron acceptor material
  • Electron acceptor material for organic solar cell as well as preparation method and application of electron acceptor material

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 as well as a preparation method and application of the electron acceptor material. The method uses benzotrithiophene asa core, different quantity of thiophene unit bridges are introduced, a strong electron withdrawing group is introduced at the tail end to realize adjustment and control of photoelectric properties, and therefore the high-performance electronic acceptor material for the organic solar cell is built. The electron acceptor material for the organic solar cell disclosed by the invention shows excellentexciton separation ability, has good thermal stability, electrical stability and solution processing performance, is simple to synthesize and easy to purify, has low costs, and is potential replacement of a fullerene electron acceptor, and suitable for being used as a non-fullerene electron acceptor material to be widely used to prepare high-performance devices for the organic solar cell.

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 Applications(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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