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Copolymer containing perylenetetracarboxylic diimide-s-indacenobithiophene, preparation method thereof and applications thereof

A technology containing perylene tetracarboxylic acid diimide and perylene tetracarboxylic acid diimide, applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, luminescent materials, etc., can solve the problem of reducing the photoelectric conversion efficiency of organic semiconductor devices , can not effectively use sunlight, and the matching degree of emission spectrum is not high enough to achieve excellent charge transport performance, improve solution processability, and good solubility

Inactive Publication Date: 2014-03-12
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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Problems solved by technology

However, since perylenetetracarboxylic acid diimide and its derivatives contain a large planar conjugated system and good molecular coplanarity, the interaction of large π bonds between molecules is very strong and has a large lattice energy, so It has poor solubility and poor film-forming processability, which leads to the phase separation problem of the prepared device, which affects the efficiency of exciton diffusion, resulting in energy loss
In addition, since the absorption spectrum of perylenetetracarboxylic diimide and its derivatives is mainly concentrated in the visible region, the absorption range is not wide enough, and the matching degree with the emission spectrum of sunlight is not high enough, so the sunlight cannot be effectively used, and the Will reduce the photoelectric conversion efficiency of organic semiconductor devices

Method used

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  • Copolymer containing perylenetetracarboxylic diimide-s-indacenobithiophene, preparation method thereof and applications thereof
  • Copolymer containing perylenetetracarboxylic diimide-s-indacenobithiophene, preparation method thereof and applications thereof
  • Copolymer containing perylenetetracarboxylic diimide-s-indacenobithiophene, preparation method thereof and applications thereof

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Experimental program
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preparation example Construction

[0029] The preparation method of the above-mentioned copolymer containing perylenetetracarboxylic acid diimide-symmetric indaprothodithiophene, comprises the steps:

[0030] S1. Under an inert atmosphere (including an inert atmosphere composed of nitrogen, argon or a mixture of nitrogen and argon), the structural formula is The compound A (perylenetetracarboxylic diimide dibromide) with the structural formula is The compound B (2,7-bistributyltin-symmetric indaprodithiophene derivative) was added into the solvent where the catalyst was present at a molar ratio of 1:1~1:1.2, and the Stille coupling was carried out at 50~120°C React 24~72 hours, stop reaction, make containing structural formula: The reaction solution of the copolymer containing perylenetetracarboxylic acid diimide-symmetric indaprodithiophene; in the above formulas: n is an integer between 1-100; R 1 , R 2 , R 3 Same or different hydrogen, C 1 ~C 20 Alkyl or C 1 ~C 20 Alkoxy; R 4 for C 1 ~C 20 Alky...

Embodiment 1

[0040] The copolymer containing perylenetetracarboxylic acid diimide-symmetric indaprodithiophene in this example is poly N,N'-di-(3,4,5-tri-dodecyloxybenzene) -3,4,9,10-perylenediimide-4,4,9,9-tetrakis(dodecyl)symmetric indaeo[3,2-b:7,6-b']di Thiophene (n=56):

[0041]

[0042] Under the protection of nitrogen, the compound N,N'-bis-(3,4,5-tri-dodecyloxybenzene)-1,7-dibromo-3,4,9,10-perylenediyl Imine 0.5mmol, 2,7-bistributyltin-4,4,9,9-tetrakis(dodecyl)symmetric indapro[3,2-b:7,6-b']dithiophene 0.5 1 mmol of DMF solvent (18 mL) was dissolved. Continue to feed nitrogen bubbles for 0.5h to remove residual oxygen. Then join Pd 2 (dba) 3 (0.0.14g, 0.015mol) and P(o-Tol) 3 (0.0083g, 0.027mmol), continue to bubble nitrogen gas for 0.5h to remove residual oxygen, and then heat to 80°C for Stille coupling reaction for 48 hours. The reaction was stopped, and the reaction liquid was added dropwise to methanol for sedimentation. Suction filtration, washing with methanol, and...

Embodiment 2

[0044] The copolymer containing perylenetetracarboxylic acid diimide-symmetric indaprodithiophene in this example, that is, poly-N,N'-di-(4-eicosyl-3,5-dimethoxy Benzene)-3,4,9,10-perylenediimide-4,4,9,9-tetrakis(eicosyl)symmetric indaeo[3,2-b:7,6-b' ]dithiophene (n=43):

[0045]

[0046] Under the protection of nitrogen, to the compound NN,N'-bis-(4-eicosyl-3,5-dimethoxybenzene)-1,7-dibromo-3,4,9,10-perylene Diimide 0.5mmol, 2,7-bistributyltin-4,4,9,9-tetrakis(eicosyl)symmetric indaeo[3,2-b:7,6-b']di Dissolve 0.5 mmol of thiophene in dioxane solvent (15 mL). Continue to feed nitrogen bubbles for 0.5h to remove residual oxygen. Then add Pd(PPh 3 ) 2 Cl 2 (10mg, 0.014mmol), continue to bubble nitrogen gas for 0.5h to remove residual oxygen, and then heat to 120°C for Stille coupling reaction for 24 hours. The reaction was stopped, and the reaction liquid was added dropwise to methanol for sedimentation. Suction filtration, washing with methanol, and drying. Then it ...

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses a copolymer containing perylenetetracarboxylic diimide-s-indacenobithiophene, a preparation method thereof and applications thereof. The copolymer has a general structure formula as follows, wherein n is an integer between 1 and 100; R1, R2 and R3 are the same or different and are selected from hydrogen, C1-C20 alkyl or C1-C20 alkoxy; and R4 is C1-C20 alkyl or C1-C20 alkylbenzene. According to the copolymer, the s-indacenobithiophene unit and the perylenetetracarboxylic diimide are subjected to copolymerization to form an electron donor-receptor structure so as to adjust the bad gap of the polymer and to push the absorption band edge of the polymer to infrared and near infrared zones, thus increasing the sunlight utilization rate and further increasing the light conversion rate.

Description

technical field [0001] The invention relates to organic semiconductor materials, in particular to a copolymer containing perylenetetracarboxylic acid diimide-symmetric indaeodithiophene and its preparation method and application. Background technique [0002] The preparation of low-cost and high-efficiency organic semiconductor devices using cheap materials, such as organic solar cells, organic electroluminescent devices, and organic field-effect transistors, has always been a research hotspot and difficulty in the field of photovoltaics. Silicon solar cells currently used on the ground are limited in application due to complex production processes and high costs. In order to reduce the cost and expand the scope of application, people have been looking for new solar cell materials for a long time. Organic semiconductor devices have attracted much attention due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area ...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/46H01L51/54H01L51/30
CPCH01L51/0053Y02E10/549H10K85/621
Inventor 周明杰管榕黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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