A kind of organic photovoltaic material based on perylene imide and its preparation method and application

An organic photovoltaic material, nitroperylene imide technology, applied in the fields of organic chemistry, photovoltaic power generation, semiconductor/solid-state device manufacturing, etc., can solve the problem that the performance of non-fullerene electron acceptor materials is difficult to effectively control and the light absorption effect is not good. Ideal, complex material preparation method and other problems, to achieve the effect of low synthesis cost, fewer synthesis steps, and simple synthesis method

Active Publication Date: 2021-02-02
NANJING UNIV OF POSTS & TELECOMM
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Problems solved by technology

[0004] Technical problem: The present invention provides a perylene imide-based organic photovoltaic material and its preparation method and application to solve the problem of poor stability of current non-fullerene electron acceptor materials, unsatisfactory light absorption effect, complicated material preparation methods, and low cost. Advanced problems, overcoming the difficulty of effectively regulating the properties of non-fullerene electron acceptor materials

Method used

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  • A kind of organic photovoltaic material based on perylene imide and its preparation method and application
  • A kind of organic photovoltaic material based on perylene imide and its preparation method and application
  • A kind of organic photovoltaic material based on perylene imide and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of PDINCB

[0041]

[0042] PDI-NO 2 : PDI (10g, 14.3mmol) was dissolved in 500mL of dichloromethane, fuming nitric acid (10mL) was added dropwise in the above PDI solution, stirred at room temperature, the reaction solution was washed with sodium hydroxide, extracted three times with dichloromethane , with MgSO 4 Drying followed by purification by column chromatography afforded PDI-NO 2 (8 g), 75% yield. Such as figure 1 as shown, 1 H NMR (400MHz, CDCl 3,δ,ppm):9.78(d,J=8.3Hz,1H),8.92(s,1H),8.64(t,J=17.8Hz,5H),5.17(qd,J=9.7,4.7Hz,2H) ,2.30-2.16(m,4H),1.91-1.77(m,4H),1.36-1.22(m,24H),0.83(t,J=6.8Hz,12H). 13 C NMR (101MHz, CDCl 3 ,δ,ppm):164.32(s),165.05-161.78(m),161.78-160.77(m),147.68(s),135.46(s),133.29(s),132.94(s),132.24(d,J =134.2Hz), 131.13(s), 129.56-129.04(m), 127.90(s), 127.74-126.33(m), 126.14(s), 124.47(s), 124.01(s), 55.25(s), 54.96 (s), 32.22(d, J=9.0Hz), 31.69(d, J=2.6Hz), 26.58(d, J=1.9Hz), 23.09-22.15(m), 14.02...

Embodiment 2

[0047] Embodiment 2: Preparation of 2PDINCB

[0048]

[0049] 2PDINCB: PDI-NH 2 (1g, 1.4mmol) and terephthalaldehyde (54mg, 0.4mmol) were dissolved in absolute ethanol, added 1mL acetic acid, stirred overnight at 80°C, extracted with DCM, MgSO 4 Drying and purification by column chromatography afforded 2PDINCB (964 mg) in 91% yield. Such as Figure 4 as shown, 1 H NMR (400MHz, CDCl 3 ,δ,ppm)9.11(d,J=8.3Hz,2H),8.99(s,2H),8.78-8.66(m,10H),8.38(s,6H),5.27-5.16(m,4H),2.28 (dd,J=15.5,6.1Hz,8H),1.92-1.81(m,8H),1.29(dd,J=17.3,6.0Hz,48H),0.84(dd,J=13.4,6.7Hz,24H). Such as Figure 5 as shown, 13 C NMR (101MHz, CDCl 3 ,δ,ppm)164.81(d,J=11.5Hz),163.72(d,J=5.8Hz),161.25(s),149.32(s),139.02(s),134.94-134.17(m),131.86(s ),131.13(s),130.42(s),129.09(s),127.95(s),127.57(s),127.09(s),125.79(s),123.54(s),122.49(s),55.21-54.99 (m), 54.80(d, J=22.0Hz), 32.34(s), 31.78(s), 29.72(s), 26.67(d, J=4.0Hz), 22.60(d, J=2.8Hz), 14.08 (d, J=3.0Hz). Such as Figure 6 Shown, Calcd for MS: 1524...

Embodiment 3

[0050] Embodiment 3: Preparation of PDINCF

[0051]

[0052] PDINCF: PDI-NH 2 (1g, 1.4mmol) and fluorenaldehyde (256mg, 4mmol) were dissolved in absolute ethanol, added 1mL acetic acid, stirred overnight at 80°C, extracted with DCM, MgSO 4 After drying and purification by column chromatography, PDINCF (0.97 g) was obtained in 93% yield.

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Abstract

The invention discloses an organic photovoltaic material based on perylene imide, a preparation method and application thereof. The organic photovoltaic material is composed of peryleneimide as a basic building block, which is connected with different conjugated groups through carbon-nitrogen double bonds. The organic photovoltaic material is prepared by condensation of aminoperyleneimide and monoaldehyde conjugated group or bisaldehyde conjugated group through Schiff base reaction. Commercialized organic photovoltaic materials. The obtained organic photovoltaic material has good thermal stability, electrical stability and solution processability, and can be applied to prepare organic solar cell devices such as binary, multi-component or stacked layers.

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials, and in particular relates to a perylene imide-based organic photovoltaic material and its preparation method and application. Background technique [0002] Organic solar cells (OSCs) can be used to fabricate large-area flexible thin-film battery modules by green and low-cost printing technology, showing great potential for development. Over the past two decades, significant progress has been made in electron donor materials and fullerene-based electron acceptor materials for organic solar cells. However, the shortcomings of fullerene-based electron acceptor materials limit the further improvement of the photoelectric conversion efficiency of organic solar cells, such as weak light absorption in the visible spectrum region, limited energy level adjustment, high synthesis cost, and poor shape stability. In recent years, the development of non-fullerene electron acceptor materials...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/06C07D519/00H01L51/46
CPCC07D471/06C07D519/00H10K85/623H10K85/621H10K85/615H10K85/6572Y02E10/549Y02B10/10
Inventor 赖文勇左超李祥春汪洋黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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