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Organic photovoltaic material as well as preparation method and application thereof

An organic photovoltaic material and reaction technology, applied in photovoltaic power generation, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problems of low efficiency of wide bandgap materials, ternary and laminated device preparation difficulties, etc., and achieve easy reaction process Control, easy adjustment of energy level and spectrum, high yield effect

Inactive Publication Date: 2018-11-23
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Purpose of the invention: In order to overcome the shortcomings of electron acceptor materials in the prior art, the present invention provides an organic photovoltaic material and its preparation method and application, specifically a high Organic photovoltaic materials with photoelectric conversion efficiency and their preparation methods and applications. The application of this material as an electron acceptor material can solve the problems of low efficiency of wide bandgap materials and difficulties in preparing ternary and stacked devices.

Method used

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

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation process of IDDT-TBA:

[0036] 6,6,12,12-Tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2',3'-d']-s-benzobisindeno [1,2-B:5,6-b']dithiophene-2,8-dicarbaldehyde (107.4 mg, 0.1 mmol) and TBA (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-TBA (96.8 mg, 90.1%) as a dark blue solid. Implementation route:

[0037]

[0038] Such as image 3 as shown, 1 H NMR (400MHz, CDCl 3 ): δ8.65(s,2H), 8.16(s,2H), 7.62(s,2H), 7.22(d,8H), 7.13(d,8H), 4.58(m,8H), 2.56(m, 8H), 1.62-1.59 (m, 8H), 1.38-1.27 (m, 36H), 0.90-0.84 (m, 12H). Such as Figure 6 as shown, 13 C NMR (101MHz, CDCl 3 ):δ178.57,161.03,...

Embodiment 2

[0041] The preparation process of IDT-TBA: 4,4,9,9-tetra(4-hexylphenyl)-4,9-dihydro-s-benzobisindeno[1,2-B:5,6- B']dithiophene-2,7-dicarbaldehyde (96.25mg, 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°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-TBA as a dark blue solid. (93.4 mg, 97%).

[0042] Implementation route:

[0043]

[0044] Such as figure 1 as shown, 1 H NMR (400MHz, CDCl 3 ): δ8.67(s,2H), 7.78(s,2H), 7.74(s,2H), 7.30(d,8H), 7.26(d,8H), 7.14-7.08(m,8H), 4.63- 4.54 (m, 8H), 2.59-2.55 (m, 8H), 1.59-1.21 (m, 36H), 0.89-0.85 (m, 12H). Such as Figure 5 as shown, 13 C NMR (101MHz, CDCl 3 ):δ178.51,160.86,160.05,159.77,157.67,156.12,149.76,142.3...

Embodiment 3

[0047] 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°C. 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 the eluent was purified to obtain FTC8-TBA as a dark blue solid.

[0048] Implementation route:

[0049]

[0050] Such as Figure 4 as shown, 1 H NMR (400MHz, CDCl 3 )δ8.72(s,2H),7.96-7.95(d,2H),7.88(d,2H),7.83-7.79(m,4H),7.67-7.66(m,2H),4.70-4.60(m, 8H), 2.16-2.12(m,4H).

[0051] Figure 7 It is the thermal weight loss curve of IDDT-TBA. It can be seen that the material will reach the glass transition temperature w...

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Abstract

The invention discloses an organic photovoltaic material as well as a preparation method and application thereof. The invention belongs to the technical field of photovoltaic and specifically relatesto the organic photovoltaic material with a thiobarbituric acid group (TBA) as a terminal group as well as the preparation method and the application thereof. The material utilizes the thiobarbituricacid group (TBA) as the terminal group and one or several donor units as bridging frameworks. The material disclosed by the invention has the characteristics of simpleness in preparation, reaction process which is easy to control, easiness in separation and purification, energy level and spectrum which are easy to adjust and the like. Furthermore, the material further shows good thermal stability,film formation stability and higher electron and hole mobility, and a photovoltaic device prepared by the material has higher photoelectric conversion efficiency and potential application value in the 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 optoelectronic 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 conversion efficiency of organic photovoltaic devices based on polymers or small molecules has exceeded 15%, 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 polydispersity of molecular we...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22C07D495/04C07D409/14H01L51/46H01L51/54
CPCC07D409/14C07D495/04C07D495/22H10K85/615H10K85/654H10K85/6576Y02E10/549
Inventor 赖文勇公彦婷李祥春黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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