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

A perylene tetracarboxylic acid diimide copolymer and perylene tetracarboxylic acid diimide technology are applied in the field of polymer materials, preparation, and perylene tetracarboxylic acid diimide copolymers containing naphthodithiophene units. It can solve the problems of insufficient matching of emission spectrum, inability to effectively use sunlight, and poor film-forming processing performance, and achieve good solubility, excellent charge transport performance, and favorable film-forming processing effects

Inactive Publication Date: 2011-12-28
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

[0005] 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 perylene tetracarboxylic acid diimide copolymer containing naphthodithiophene unit with good solubility, strong absorbance, and excellent charge transport performance

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1

[0041] Example 1, Poly N, N'-bis-(3,4,5-tri-methylbenzene)-3,4,9,10-perylene diimide-(5,6-dihexyl)naphtho [2,1-b:3,4-b']dithiophene, wherein n is 25, the structural formula is as follows:

[0042]

[0043] Preparation method: under nitrogen protection, add 0.5mmol N,N'-bis-(3,4,5-tri-methylbenzene)-1,7-dibromo-3,4,9,10-perylene to 18mL The DMF solution of diimide and 0.5mmol 2,9-bistributyltin-(5,6-di-hexyl)naphtho[2,1-b:3,4-b']dithiophene was removed by blowing nitrogen for 0.5h residual oxygen. Then add 0.0.14g (0.015mol) of Pd 2 (dba) 3 and 0.0083g (0.027mmol) of P(o-Tol) 3 , Nitrogen was blown again for 0.5h to remove residual oxygen, and then heated to 80°C for 48 hours. The reacted mixed liquid was added dropwise into methanol for sedimentation to obtain a sediment. The precipitate was filtered with suction, washed with methanol, dried and dissolved in toluene, then added to the aqueous solution of sodium diethyldithiocarbamate, heated to 90°C and stirred for 8-...

Embodiment 2

[0044] Example 2 Poly N, N'-bis-(3,4,5-tri-methoxybenzene)-3,4,9,10-perylenediimide-(5-hexyl-6-decyl) Naphtho[2,1-b:3,4-b']dithiophene, wherein n is 21, the structural formula is as follows:

[0045]

[0046] Preparation method: Under the protection of nitrogen, add 0.5mmol N,N'-bis-(3,4,5-tri-methoxybenzene)-1,7-dibromo-3,4,9,10- to 15mL Dioxane solution of perylene diimide and 0.5 mmol 2,9-bistributyltin-(5-hexyl-6-decyl)naphtho[2,1-b:3,4-b']dithiophene Nitrogen was blown for 0.5h to remove residual oxygen. Then add 10mg Pd(PPh 3 ) 2 Cl 2 , and then bubbling nitrogen for 0.5h to remove residual oxygen, then heated to 85°C for 36 hours. The reacted mixed liquid was added dropwise into methanol for sedimentation. After settling, filter with suction, wash with methanol, dry and dissolve with toluene, add to the aqueous solution of sodium diethyldithiocarbamate, heat the mixture to 90°C and stir for 8 to 14 hours. The reacted organic phase was subjected to column chrom...

Embodiment 3

[0047] Example 3 Poly N, N'-bis-(3,4,5-tri-octyloxybenzene)-3,4,9,10-perylene diimide-(5,6-bis-eicosane Base) naphtho[2,1-b:3,4-b']dithiophene, wherein, n is 11, and the structural formula is as follows:

[0048]

[0049] Preparation method: Under nitrogen protection, add 0.5mmol N,N'-bis-(3,4,5-tri-octyloxybenzene)-1,7-dibromo-3,4,9,10- to 30mL Perylene diimide and 0.5 mmol 2,9-bistributyltin-(5,6-di-eicosyl)naphtho[2,1-b:3,4-b']dithiophene in toluene and THF The mixed solution was blown with nitrogen for 0.5h to remove residual oxygen. Then add 8mg Pd(PPh 3 ) 4 , Nitrogen was blown again for 0.5h to remove residual oxygen, and then heated to 80°C for 72 hours. Add the reacted mixed solution dropwise to methanol for sedimentation, filter it with suction after sedimentation, wash with methanol, and dissolve it with toluene after drying, add it to the aqueous solution of sodium diethyldithiocarbamate, heat to 80°C and stir for 8~ 14 hours. The reacted organic phase was...

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Abstract

The invention discloses thiophanthrene unit-containing perylene tetracarboxylic diimide copolymer and a preparation method as well as application thereof. The preparation method of the copolymer comprises the following steps of: putting perylene tetracarboxylic diimide dibromide and a 2,6-bis(tributyl tin)-naphtho [2,1-b:3, 4-b'] dithiophene derivative serving as raw materials in an organic solvent; adding a catalyst to perform Stille coupling reaction at the temperature of 50-120 DEG C for 24-72 hours; and refining to obtain the copolymer. The copolymer is applied to manufacturing of a polymer solar cell device, manufacturing of an organic field effect transistor, manufacturing of an organic electroluminescent device, manufacturing of an organic light storage device, manufacturing of an organic nonlinear material and manufacturing of an organic laser device. The copolymer has the advantages of high dissolubility, strong absorbency, superior charge transfer performance, capability of extending an absorption range to a near infrared region, capability of increasing utilization rate of sunlight, simple synthetic route and low technological requirements.

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 naphthodithiophene units, its preparation method and application. The perylene tetracarboxylic diimide copolymer containing naphthodithiophene units can be used in polymer solar cells, useful Applications in fields such as electromechanical luminescence, organic field effect transistors, organic optical storage, organic nonlinear materials, and organic lasers. Background technique [0002] Solar energy is one of the most promising renewable energy sources due to its outstanding advantages such as widespread and vast distribution, large amount of resources, clean and pollution-free, safe and easy to obtain. Solar cells can directly convert sunlight energy into electrical energy, which is a feasible and effective way to u...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/00H01S5/36
CPCY02E10/549H01L51/0053Y02P70/50H10K85/621
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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