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Organic photovoltaic material and preparation method and application thereof

A technology of organic photovoltaic materials and organic photovoltaic devices, which is applied in the fields of photovoltaic power generation, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problem of low spectral coverage in the near-infrared region, and achieve high photoelectric conversion efficiency, energy level and easy spectrum Adjust and prepare simple effects

Inactive Publication Date: 2019-09-10
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the shortcomings of existing electron acceptor materials, the purpose of the present invention is to provide an organic photovoltaic material and its preparation method and application. The application of this material as an electron acceptor material can solve the problem that the current spectrum coverage is less in the near-infrared region. question

Method used

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  • Organic photovoltaic material and preparation method and application thereof
  • Organic photovoltaic material and preparation method and application thereof
  • Organic photovoltaic material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of IDDT-DTM: 4,4,9,9-tetrakis(4-hexylphenyl)-4,9-dihydro-s-indacene[1,2-b:5,6-b']di Thiophene-2,7-dicarbaldehyde (107.4 mg, 0.1 mmol) and DTM (44 mg, 0.22 mmol) were dissolved in 10 mL of chloroform, then 0.1 mL of piperidine was added. The solution was stirred at 80°C for 8 hours. The mixture was then diluted with chloroform and washed three times with brine. The organic phases were combined and washed with MgSO 4 dry. After removing the solvent, the resulting residue was purified by column chromatography using hexane as eluent to give IDDT-DTM (36.8 mg, 30.1%) as a dark blue solid.

[0029] Implementation route:

[0030]

[0031] 1 H NMR (400MHz, CDCl 3 )δ8.85(d, J=7.9Hz, 2H), 8.57(s, 2H), 8.00(d, J=6.6Hz, 1H), 7.87(dd, J=13.8, 7.1Hz, 2H), 7.72( s,1H),7.53(d,J=8.3Hz,1H),7.15(s,8H),2.60–2.54(m,4H).MALDI-TOF-MS(m / z): Calcd for C 92 h 82 N 4 o 4 S 6 ,Exact Mass:M + 1498.47; Found: 1498.356 (M + ).

[0032] Device preparation: first patterned...

Embodiment 2

[0034] The preparation process of IDT-C8: 4,4,9,9-tetrakis(4-hexylphenyl)-4,9-dihydro-s-benzobisindeno[1,2-B:5,6- B']dithiophene-2,7-dicarbaldehyde (96.25mg, 0.1mmol) and DTM (44mg, 0.22mmol) were placed in a two-necked reaction flask, and after adding 10mL of ethanol, slowly heated to 80°C until all the reactants were dissolved. After adding 0.1mL of triethylamine to ethanol, the solution turns red-blue. After the reaction, the product precipitates out of ethanol. After filtration, it is purified by column chromatography using hexane as the eluent to obtain IDT-C8 as a dark blue solid. (33.4 mg, 37%).

[0035] Implementation route:

[0036]

[0037] 1 H NMR (400MHz, CDCl 3 )δ8.89(d, J=7.6Hz, 2H), 8.03(d, J=6.6Hz, 1H), 7.92–7.85(m, 2H), 7.80(s, 1H), 7.57(s, 2H).

[0038] Device preparation: first patterned ITO (sheet resistance=15Ωsq -1 ) glass substrates were pre-cleaned by sequential ultrasonication in detergent, deionized water, acetone, and isopropanol. And the su...

Embodiment 3

[0040] The preparation process of FTBr-TBA: the precursor 5,5'-(9,9-bis(6-bromohexyl)-9H-fluorene-2,7-diyl)bis(thiophene-2-carbaldehyde) (71.5mg ,0.1mmol) and TBA (44mg, 0.22mmol) were placed in a two-necked reaction flask, and after adding 10mL of ethanol, slowly heated to 80 degrees Celsius. Since the precursor had an alkyl chain bromide and had a high structural activity, there was no need to add it later Catalyzed by any base, the solution slowly turned blue-purple after 8 hours of reaction. After the reaction was completed, the column chromatography using hexane as eluent was purified to obtain FTC8-DTM as a dark blue solid.

[0041] Implementation route:

[0042]

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Abstract

The invention discloses an organic photovoltaic material, a preparation method and application thereof. The material takes 3-(dicyanomethylene)-2, 3-dihydrobenzothiophene-1, 1-Dioxide (DTM) as an endgroup and one or more donor units as a bridging framework, and has a structural general formula shown in a formula I, wherein D and D1 are conjugated structural system bridging units. The organic photovoltaic material of the invention has the characteristics of simple preparation, easy control of reaction process, easy separation and purification, easy adjustment of energy level and spectrum and the like. The material also has good thermal stability, film forming stability and high electron and hole mobility, and a photovoltaic device prepared by the material has high photoelectric conversionefficiency and has potential application value in the technical field of photovoltaic.

Description

technical field [0001] The invention belongs to the field of photovoltaic technology, and in particular relates to an organic photovoltaic material and its preparation method and application. Background technique [0002] Organic photovoltaic devices are photoelectric conversion devices prepared with organic semiconductors as active materials for photoelectric conversion. Compared with inorganic photovoltaic devices, it has the advantages of low cost, thin thickness, light weight, simple manufacturing process, and can be made into large-area flexible devices. One of the research frontiers of vitality. In recent years, the photoelectric conversion efficiency of organic photovoltaic devices based on polymers or small molecules has exceeded 16%, which shows the great application prospects of organic photovoltaic devices. Among them, polymer materials have limited the further development of organic photovoltaic materials due to some of their own characteristics, such as polydi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D495/22C07D333/60H01L51/46
CPCC07D495/04C07D495/22C07D333/60H10K85/655H10K85/615H10K85/6576Y02E10/549
Inventor 赖文勇公彦婷李祥春黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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