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Naphthalenetetracarboxylic acid diimide copolymer containing benzothiophene, and preparation method and application thereof

A technology of benzothiophene naphthalene tetracarboxylic acid diimide and thiophene naphthalene tetracarboxylic acid diimide, applied in the field of organic semiconductor materials, can solve problems such as low photoelectric conversion efficiency, and achieve excellent stability and charge transport performance , Improve the utilization rate, the effect of strong absorbance

Active Publication Date: 2012-05-16
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In view of this, an embodiment of the present invention provides a benzothiophene naphthalene tetracarboxylic acid diimide copolymer to solve the technical problem of low photoelectric conversion efficiency of organic semiconductor materials in the prior art

Method used

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  • Naphthalenetetracarboxylic acid diimide copolymer containing benzothiophene, and preparation method and application thereof
  • Naphthalenetetracarboxylic acid diimide copolymer containing benzothiophene, and preparation method and application thereof
  • Naphthalenetetracarboxylic acid diimide copolymer containing benzothiophene, and preparation method and application thereof

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preparation example Construction

[0024] The embodiment of the present invention also provides a method for preparing a benzothiophene naphthalene tetracarboxylic diimide copolymer, comprising the following steps:

[0025] Respectively provide naphthalene tetracarboxylic acid diimide dibromide derivative of structural formula (I) and 2,6-bistributyltin-benzo[1,2-b:4,5-b']dithiophene of structural formula (II) derivative;

[0026] Under anaerobic conditions, the naphthalene tetracarboxylic diimide dibromide derivative of the structural formula (I) and the 2,6-bistributyltin-benzo[1 , 2-b: 4,5-b']dithiophene derivatives are dissolved in a solvent, and a Stille coupling reaction is carried out at a temperature of 50-120°C and a catalyst for 24-72 hours to obtain naphthalene tetracarboxylic acid containing a silole unit Two imide copolymers, the reaction formula is expressed as:

[0027]

[0028] Among them, n, R 1 , R 2 , R 3 , R 4 The value of is the same as above, and will not be elaborated here.

[0...

Embodiment 1

[0057] Embodiments of the present invention Poly N, N'-bis-(2-octyldecyl)-1,4,5,8-naphthalene diimide-2,6-(4,8-di-hexyloxy) Benzo[1,2-b:4,5-b']dithiophene (P1) has the following structural formula:

[0058]

[0059] Among them, n is 22;

[0060] Its preparation method is as follows:

[0061] Under nitrogen protection, 0.5 mmol of N, N'-bis-(2-octyldecyl)-2,6-dibromo-1,4,5,8-naphthalene diimide, 0.5 mmol 2, 6-bistributyltin-(4,8-di-hexyloxy)benzo[1,2-b:4,5-b']dithiophene was added to DMF (18mL), bubbled for 0.5h to remove residual Oxygen, then add (0.014g, 0.015mmol) of Pd 2 (dba) 3 and (0.0083g, 0.027mmol) of P(o-Tol) 3 , continue bubbling for 0.5h to remove residual oxygen, and then heat to 80°C for 48 hours to obtain A mixed solution of imine-2,6-(4,8-di-hexyloxy)benzo[1,2-b:4,5-b']dithiophene. The mixture was added dropwise to methanol for sedimentation, suction filtered, washed with methanol, dried, dissolved in toluene, added to an aqueous solution of sodium die...

Embodiment 2

[0064] Examples of the present invention Poly N, N'-bis-(2-hexyloctyl)-1,4,5,8-naphthalene diimide-2,6-(4,8-di-octyloxy)benzene And[1,2-b:4,5-b']dithiophene (P2) has the following structural formula:

[0065]

[0066] Among them, n is 29;

[0067] Its preparation method is as follows:

[0068] Under nitrogen protection, 0.5 mmol of N, N'-bis-(2-hexyloctyl)-2,6-dibromo-1,4,5,8-naphthalene diimide, 0.5 mmol of 2, 6-bistributyltin-(4,8-di-octyloxy)benzo[1,2-b:4,5-b']dithiophene was added to dioxane (15mL) and bubbled for 0.5h Remove residual oxygen, then add Pd(PPh 3 ) 2 Cl 2 10mg, bubbled for 0.5h to remove residual oxygen, and then heated to 85°C for 36 hours to obtain Mixed solution of amine-2,6-(4,8-di-octyloxy)benzo[1,2-b:4,5-b']dithiophene. The mixture was added dropwise to methanol for sedimentation, suction filtered, washed with methanol, and dried. It was then dissolved in toluene, added to an aqueous solution of sodium diethyldithiocarbamate, and the mixture...

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Abstract

The invention is applicable to the technical field of organic semiconductor materials, and provides a naphthalenetetracarboxylic acid diimide copolymer containing benzothiophene unit, and a preparation method and application thereof. The copolymer has the following structural formula. The benzothiophene unit and the naphthalenetetracarboxylic acid diimide unit are polymerized, so that the copolymer provided by the invention has the advantages of high solubility, strong absorbance, wide light absorption range and the like; the light absorption range can be extended to the near infrared region,so that the sunlight utilization ratio is enhanced; and meanwhile, the naphthalenetetracarboxylic acid diimide copolymer containing benzothiophene has excellent stability and charge transmission performance.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a benzothiophene naphthalene tetracarboxylic acid diimide copolymer, its preparation method and application. Background technique [0002] The application of polymer organic semiconductor materials in solar cells has attracted much attention due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating, printing, etc., but polymer organic semiconductor materials in the prior art Due to the relatively low carrier mobility, the spectral response does not match the solar radiation spectrum, the red light region with high photon flux is not effectively utilized, and the electrode collection efficiency of carriers is low, making polymer organic semiconductor materials The low photoelectric conversion efficiency has become an obstacle affecting its application. Contents...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/30H01L51/46H01L51/54H01S5/36
CPCY02E10/549
Inventor 周明杰黄杰管榕
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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