A kind of ortho-bridged perylene diimide dimer and its preparation method and application in organic photovoltaic devices

A dimer, ortho-position technology, applied in the fields of electrical solid device, semiconductor device, semiconductor/solid-state device manufacturing, etc., can solve the problems of destroying the order of PDI molecular π system, deformation, unfavorable carrier effective transport, etc. Achieve the effect of reducing excessive aggregation, reducing size, and avoiding deformation

Active Publication Date: 2020-07-14
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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  • A kind of ortho-bridged perylene diimide dimer and its preparation method and application in organic photovoltaic devices
  • A kind of ortho-bridged perylene diimide dimer and its preparation method and application in organic photovoltaic devices
  • A kind of ortho-bridged perylene diimide dimer and its preparation method and application 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 thereof and an application thereof in the field of organic photovoltaics. The invention also relates to organic solar cells of such compounds and methods for their preparation. Compared with PDI monomer molecules, the formed twisted dimer structure can effectively weaken the excessive aggregation between PDI molecules, thereby reducing the phase size. At the same time, the deformation of the PDI core caused by bridging at the waist can be avoided through the bridging at the adjacent position, so that it can maintain a certain planarity and strong π-π stacking, and obtain higher electron mobility. Using the PDI dimer as an acceptor material and combining it with an electron-donating polymer, an organic solar cell is prepared, and a high photoelectric conversion efficiency is achieved.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic materials, and relates to a perylene diimide small molecule dimer connected by an ortho position, a preparation method thereof, and an application thereof in the field of organic photovoltaics. Background technique [0002] Solar energy has the advantages of cleanness, 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 way. [0003] Compared with inorganic semiconductor photovoltaic materials, solution-processable organic polymers and small molecule photovoltaic materials have the advantages of lower cost and suitable for large-area flexible processing. The donor materials in the battery active layer can be divided into polymers and small molecules. Compared with polymer materials, organic small molecule materials have the advantages of clear structure...

Claims

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Application Information

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Patent Type & Authority Patents(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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