Ortho-bridged perylene diimide dimer, preparation method and application thereof in organic photovoltaic devices

A perylene diimide dimer and dimer technology, which is applied in the fields of electric solid-state devices, semiconductor devices, semiconductor/solid-state device manufacturing, etc., can solve the problem of effective transport of unfavorable carriers and destroy the order of the PDI molecular π system Sexuality, deformation and other problems, to reduce the effect of excessive aggregation

Active Publication Date: 2017-10-31
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, although this distortion reduces the phase size, the bridging unit at the waist position will cause the deformation of the two naphthalene rings in the PDI core, seriously destroying the order of the PDI molecular π system, which is not conducive to the carrier flow. efficient transmission

Method used

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  • Ortho-bridged perylene diimide dimer, preparation method and application thereof in organic photovoltaic devices
  • Ortho-bridged perylene diimide dimer, preparation method and application thereof in organic photovoltaic devices
  • Ortho-bridged perylene diimide dimer, preparation method and application thereof in organic photovoltaic devices

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: Preparation of PDI monomer 1a substituted by ortho-position Br

[0058]

[0059] Ortho Br-substituted PDI monomer 1a according to the literature (K.Müllen et al, Org. Lett., 2011, 13, 3012-3015; H.Shinokubo et al, Org. Lett., 2011, 13, 2532-2535) method of preparation.

Embodiment 2

[0060] Embodiment 2: preparation compound 2a

[0061]

[0062] The product 1a (855.6 mg, 1.1 mmol) was dissolved in 15 mL of toluene, and commercially available thiophene-2,5-di-tributyltin (332.1 mg, 0.5 mmol) and Pd (PPh 3 ) 4 (34.7mg, 0.03mmol), under the heating condition of 120°C, the reaction was stirred for 36 hours. The toluene in the reaction system was distilled off under reduced pressure to obtain a red-black solid, which was dissolved in a mixed solvent of 50 mL of dichloromethane and 50 mL of water, the dichloromethane layer was collected by liquid separation, and the dichloromethane was distilled off under reduced pressure to obtain a red The black solid was passed through the H60 silica gel column to obtain the product 2a (628.2 mg, 0.425 mmol, yield: 85%). 1 H NMR (400MHz, CDCl 3 ):δppm:8.68-8.62(m,14H),7.49-7.37(m,2H),5.21-5.13(m,4H),2.28-2.21(m,8H),1.87-1.80(m,8H),1.36 -1.15(m,48H),1.14-0.96(m,24H). MS(MALDI-TOF):m / z=1477.2[M+H] + .

Embodiment 3

[0063] Example 3: Preparation of Trimethyltin Derivatives Used in Examples 4-7

[0064] Oligothiophene was synthesized according to the literature (N.Tamaoki et al, J.Am.Chem.Soc., 2006, 128, 10930-10933).

[0065] The trimethylstanning reaction was prepared as follows: oligothiophene, selenophene, benzene, or furan (1 mmol) was dissolved in 10 mL of anhydrous THF. Argon protection, cooled to -78 ℃. A commercially available 2.2 mol / L n-butyllithium solution in n-hexane (1 mL, 2.2 mmol) was slowly added. After stirring at -78°C for 2 hours, a commercially available 1 mol / L (25 wt.%) trimethyltin chloride solution in n-hexane (2.5 mL, 2.5 mmol) was added. After the reaction system was warmed to room temperature, stirring was continued for 2 hours. The mixed solution was diluted with 50 mL of ethyl acetate. After washing three times with water, dry and spin dry. The residue was recrystallized with methanol at -20°C, and the corresponding trimethyltin derivatives could be sep...

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Abstract

The invention provides an ortho-bridged perylene diimide dimer (formula I), a preparation method and an application thereof in the organic photovoltaic field. The invention further relates to an organic solar cell of the compound and a preparation method of the organic solar cell. Compared with a PDI monomer molecule, a formed twisted dimer structure is capable of effectively weakening excessive aggregation among PDI molecules, so that the phase size is reduced. Meanwhile, by virtue of ortho-bridging, the deformation of a PDI inner core caused by waist bridging can be avoided, so that certain planarity and relatively strong pi-pi accumulation can be maintained, and relatively high electronic mobility can be obtained. The PDI dimer is taken as a receptor material and is combined with an electron donor polymer so as to prepare the organic solar cell, so that very high photoelectric conversion efficiency is realized.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic materials, and relates to a perylene diimide type small molecule dimer linked by an ortho-position bridge, a preparation method thereof, and an application thereof in the field of organic photovoltaics. Background technique [0002] Solar energy has the advantages of clean, renewable and huge reserves. How to effectively utilize solar energy has been a research hotspot in recent years. Using solar cells to convert solar energy into electricity is a very attractive approach. [0003] Compared with inorganic semiconductor photovoltaic materials, solution-processable organic polymers and small-molecule photovoltaic materials have the advantages of low cost and suitable for large-area flexible processing. Donor materials in the active layer of batteries can be divided into polymers and small molecules. Compared with polymer materials, organic small molecule materials have the advantages of clear ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07F7/10H01L51/46H01L51/48
CPCC07D519/00C07F7/0816H10K71/12H10K85/6572H10K85/40Y02E10/549
Inventor 姚建年詹传郎姜博
Owner INST OF CHEM CHINESE ACAD OF SCI
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