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Perylene tetracarboxylic acid diimide copolymer containing dithienoquinoxaline unit, preparation method and application

A technology of perylene tetracarboxylic acid diimide copolymer and perylene tetracarboxylic acid diimide, which is applied in the directions of electrical components, final product manufacturing, sustainable manufacturing/processing, etc. The emission spectrum matching degree is not high enough, and the film-forming processing performance is poor, so as to achieve the effect of excellent charge transport performance, good solubility, and favorable film-forming processing performance.

Inactive Publication Date: 2011-12-21
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is that perylenetetracarboxylic acid diimide and its derivatives in the prior art have poor solubility, poor film-forming and processing performance, and their emission spectrum matching degree with sunlight is not high enough. , Can not effectively use the defects of sunlight, to provide a perylenetetracarboxylic acid diimide copolymer containing dithienoquinoxaline units with good solubility, strong absorbance, and excellent charge transport properties

Method used

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  • Perylene tetracarboxylic acid diimide copolymer containing dithienoquinoxaline unit, preparation method and application
  • Perylene tetracarboxylic acid diimide copolymer containing dithienoquinoxaline unit, preparation method and application
  • Perylene tetracarboxylic acid diimide copolymer containing dithienoquinoxaline unit, preparation method and application

Examples

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Effect test

Embodiment 1

[0040] Example 1 Poly N, N'-bis-(3,4,5-tri-methylbenzene)-3,4,9,10-perylene diimide-(2,3-dihexyl) dithieno [3,2-f:2',3'-h]quinoxaline, wherein n is 23, and the structural formula is as follows:

[0041]

[0042] Preparation method: under the protection of nitrogen, add 0.5 mmol of N, N'-bis-(3,4,5-tri-methylbenzene)-1,7-dibromo-3,4,9,10-perylene Diimide, 0.5mmol of 6,9-bistributyltin-(2,3-di-hexyl)dithieno[3,2-f:2',3'-h]quinoxaline in DMF (18mL ) The solution was bubbled for 0.5h to remove residual oxygen. Then add 0.015mol (0.0.14g) of Pd 2 (dba) 3 and 0.027mmol (0.0083g) of P(o-Tol) 3 , Bubbled for 0.5h to remove residual oxygen; then heated to 80 ° C for 48 hours. The reacted solution was added dropwise into methanol for sedimentation, suction filtered, washed with methanol, dried, then dissolved in toluene, added to an aqueous solution of sodium diethyldithiocarbamate, heated to 90°C and stirred overnight. The organic phase was subjected to column chromatography o...

Embodiment 2

[0043] Example 2 Poly N, N'-bis-(3,4,5-tri-methoxybenzene)-3,4,9,10-perylene diimide-(2-hexyl-3-decyl) Dithieno[3,2-f:2',3'-h]quinoxaline, wherein n is 22, the structural formula is as follows:

[0044]

[0045] Preparation method: Under the protection of nitrogen, add 0.5 mmol of N, N'-bis-(3,4,5-tri-methoxybenzene)-1,7-dibromo-3,4,9,10- Perylene diimide, 0.5mmol of 6,9-bistributyltin-(2-hexyl-3-decyl)dithieno[3,2-f:2',3'-h]quinoxaline Bubble oxane (15 mL) solution for 0.5 h to remove residual oxygen. Then add 10mg Pd(PPh 3 ) 2 Cl 2 , Bubbled for 0.5h to remove residual oxygen and then heated to 85°C for 36 hours. The reaction solution after the reaction was added dropwise into methanol for sedimentation, suction filtered, washed with methanol, and dried. Then it was dissolved in toluene, added to an aqueous solution of sodium diethyldithiocarbamate, and the mixture was heated to 90°C and stirred for 8 hours. The organic phase was subjected to column chromatography ...

Embodiment 3

[0046] Example 3 Poly N, N'-bis-(3,4,5-tri-octyloxybenzene)-3,4,9,10-perylene diimide-(2,3 di-eicosyl ) Dithieno[3,2-f:2',3'-h]quinoxaline, wherein n is 11, and the structural formula is as follows:

[0047]

[0048] Preparation method: Under the protection of nitrogen, add 0.5 mmol of N, N'-bis-(3,4,5-tri-octyloxybenzene)-1,7-dibromo-3,4,9,10- Perylene diimide, 0.5 mmol of 6,9-bistributyltin-(2,3-di-eicosyl)dithieno[3,2-f:2',3'-h]quinoxaline A mixed solution of toluene and THF (30 mL) was bubbled for 0.5 h to remove residual oxygen. Then add 8mg Pd(PPh 3 ) 4 , Bubbled for 0.5h to remove residual oxygen and then heated to 80°C for 72 hours. The reaction solution after the reaction was added dropwise into methanol for sedimentation, suction filtered, washed with methanol, and dried. Then it was dissolved in toluene, added to the aqueous solution of sodium diethyldithiocarbamate, and then the mixture was heated to 80°C and stirred for 14 hours. The organic phase was sub...

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Abstract

The invention discloses a perylene tetracarboxylic diimide copolymer containing a dithieno quinoxaline unit as well as a preparation method and application thereof. The copolymer is shown in the specification. The preparation method comprises adding a perylene tetracarboxylic diimide dibromide and a 6,9-bis(tributyl tin)-dithieno[3,2-f:2',3'-h]quinoxaline derivative in an organic solvent, adding a catalyst, carrying out Stille coupling reaction at the temperature of 50-120 DEG C for 24-72 hours, and refining to obtain the copolymer. The copolymer disclosed by the invention can be applied to manufacture of polymer solar cell devices, organic field effect transistors, organic electroluminescent devices, organic light storage devices, organic nonlinear materials or organic laser devices. Thecopolymer disclosed by the invention has the advantages of good solubility, strong light absorbency and excellent charge transfer performance, the absorption range of the copolymer can extend to a near infrared region, and the sunlight utilization rate can be increased; and the preparation method has a simple synthesis route and a low process requirement.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and relates to a polymer material, a preparation method and an application thereof. In particular, it relates to a perylene tetracarboxylic diimide copolymer containing a dithienoquinoxaline unit, a preparation method and an application thereof. The perylene tetracarboxylic diimide copolymer containing a dithienoquinoxaline unit can be used in polymers Applications in solar cells, organic electroluminescence, organic field effect transistors, organic optical storage, organic nonlinear materials, and organic lasers. Background technique [0002] Solar cells directly convert sunlight energy into electrical energy, which is a practical and effective way to utilize solar energy. At present, commercialized solar cells are mainly silicon-based inorganic solar cells. Due to the complicated production process and high cost of inorganic solar cells, the popularity and application range of inorg...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30H01L51/46H01L51/54
CPCY02E10/549Y02E10/50H01L51/0053Y02P70/50H10K85/621
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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