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Naphthalene tetracarboxyldiimide copolymer containing thienopyrroledione unit, and preparation method and application thereof

A unit naphthalene tetracarboxylic acid diimide copolymer and a unit naphthalene tetracarboxylic acid diimide technology are applied in the field of optoelectronic materials and can solve the problems of low conversion efficiency and the like

Inactive Publication Date: 2014-02-19
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the research of polymer solar cells mainly focuses on the blending system of donor and acceptor. The energy conversion efficiency of the blending system of polybenzobithiophene (PTB7) and fullerene derivative PC71BM has reached 7.4%, but it is still Much lower conversion efficiency than inorganic solar cells

Method used

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  • Naphthalene tetracarboxyldiimide copolymer containing thienopyrroledione unit, and preparation method and application thereof
  • Naphthalene tetracarboxyldiimide copolymer containing thienopyrroledione unit, and preparation method and application thereof
  • Naphthalene tetracarboxyldiimide copolymer containing thienopyrroledione unit, and preparation method and application thereof

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Experimental program
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preparation example Construction

[0062] see figure 1 , the preparation method of the diketopyrrole unit naphthalene tetracarboxylic acid diimide copolymer containing thienopyrrole unit of an embodiment, comprises the following steps:

[0063] Step S110: providing compound A and compound B.

[0064] The structural formula of compound A is:

[0065]

[0066] Among them, R 1 for C 1 ~C 20 The alkyl group or the following structural unit:

[0067]

[0068] above R 2 , R 3 , R 4 for H, C 1 ~C 20 Alkyl or C 1 ~C 20 of alkoxy. R 2 , R 3 , R 4 Can be the same or different.

[0069] C above 1 ~C 20 The alkyl group is C 1 ~C 20 straight chain alkyl or C 1 ~C 20 branched chain alkyl. C 1 ~C 20 The alkoxy group is C 1 ~C 20 Linear alkoxy or C 1 ~C 20 branched chain alkoxy.

[0070] Compound A is prepared as follows:

[0071] Compound C and Compound D are provided:

[0072] Compound C has the following structure:

[0073]

[0074] Compound D is R 1 -NH 2 , where R 1 for C 1 ~C...

Embodiment 1

[0118] Poly(N,N'-di-octyl-1,4,5,8-naphthalene tetracarboxylic diimide-5-methyl-1,3-di(thiophen-2-yl)-4H-thiophene[ Preparation of 3,4-c]pyrrole-4,6(5H)-dione

[0119] (1) Preparation of N,N'-dioctyl-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide (Compound A)

[0120] The reaction formula is:

[0121]

[0122] Compound C and compound D are provided, compound C is 2,6-dibromo-1,4,5,8-naphthalene dianhydride, and compound D is n-octylamine (C 8 h 17 NH 2 );

[0123] Under nitrogen protection, n-octylamine (compound D) (0.13 g, 1 mmol) was added to propionic acid containing 2,6-dibromo-1,4,5,8-naphthalene dianhydride (0.43 g, 0.1 mmol) (15mL) solution, refluxed for 12 hours. After cooling to room temperature, the reaction solution was poured into aqueous sodium hydroxide solution and extracted with chloroform. The organic solvent was removed, washed with ethyl acetate, dissolved in chloroform, and then subjected to column chromatography with an alumina colu...

Embodiment 2

[0135] Poly(N,N'-di-((1-octylnonyl))-1,4,5,8-naphthalene tetracarboxylic acid diimide-5-(1-octylnonyl)-1,3-di Preparation of (thiophen-2-yl)-4H-thien[3,4-c]pyrrole-4,6(5H)-dione

[0136] (1) Preparation of N,N'-di-(1-octylnonyl)-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid imide (compound A)

[0137] The reaction formula is:

[0138]

[0139] Provide compound C and compound D, compound C is 2,6-dibromo-1,4,5,8-naphthalene dianhydride, compound D is 1-octyl-nonylamine;

[0140] Under nitrogen protection, 1-octyl-nonylamine (compound D) (0.255 g, 1 mmol) was added to 2,6-dibromo-1,4,5,8-naphthalene dianhydride (compound C) ( 0.43g, 0.1mmol) of propionic acid (15mL) solution, reflux for 14 hours. After cooling to room temperature, the reaction solution was poured into aqueous sodium hydroxide solution and extracted with chloroform. The organic solvent was removed, washed with ethyl acetate, dissolved in chloroform, and then subjected to column chromatography with a...

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Abstract

The invention provides a naphthalene tetracarboxyldiimide copolymer containing a thienopyrroledione unit. The general molecular formula of the copolymer is as described in the specification. In the general molecular formula, n is an integer in a range of 5 to 100, R1 is a C1-20 alkyl group or a constitutional unit as described in the specification, R2, R3 and R4 are selected from the group consisting of alkyl groups for H and C1 to C20 and alkoxy groups for C1 to C20, and R5, R6 and R7 are selected from the group consisting of alkyl groups for H and C1 to C20. Thienopyrroledione is an excellent acceptor material. The structure of a naphthalene tetracarboxyldiimide compound includes centronucleus of polycyclic aromatic hydrocarbon and an imide group with an electron-withdrawing characteristic, and an imide unit with strong electron-withdrawing capability in the compound can reduce the energy levels of HOMO and LUMO in a material, which is beneficial for injection of electrons. The naphthalene tetracarboxyldiimide copolymer containing the thienopyrroledione unit integrates the advantages of thienopyrroledione and the naphthalene tetracarboxyldiimide compound, has excellent charge transfer performance and can improve energy conversion efficiency of semiconductor devices when applied in semiconductor devices like a solar cell.

Description

technical field [0001] The invention relates to the field of optoelectronic materials, in particular to a naphthalene tetracarboxylic diimide copolymer containing thienopyrrole diketone units and its preparation method and application. Background technique [0002] The preparation of low-cost and high-efficiency semiconductor devices using cheap optoelectronic materials has always been a research hotspot and difficulty in the field of semiconductor devices. [0003] 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 optoelectronic materials for a long time. Polymer solar cells have attracted much attention due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating and printing. If the energ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D519/00H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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