Organic semiconductor material containing naphtho-dithiadiazole and naphthalene tetracarboxylic diimide, preparation method and application of organic semiconductor material

A naphthalene tetracarboxylic acid diimide, organic semiconductor technology, applied in the field of organic semiconductor materials and their preparation, can solve the problems of low conversion efficiency and the like

Inactive Publication Date: 2014-03-26
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Abstract
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  • 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, using polybenzodithiophene (PTB7) and fullerene derivati

Method used

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  • Organic semiconductor material containing naphtho-dithiadiazole and naphthalene tetracarboxylic diimide, preparation method and application of organic semiconductor material
  • Organic semiconductor material containing naphtho-dithiadiazole and naphthalene tetracarboxylic diimide, preparation method and application of organic semiconductor material
  • Organic semiconductor material containing naphtho-dithiadiazole and naphthalene tetracarboxylic diimide, preparation method and application of organic semiconductor material

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preparation example Construction

[0062] see figure 1 , a method for preparing an organic semiconductor material containing naphthobisthiadiazole and naphthalenetetracarboxylic diimide, comprising the steps of:

[0063] Step S101, provide compound A and compound B, the structural formula of compound A is:

[0064]

[0065] Among them, R 1 for C 1 ~C 20 The alkyl group or the following structural unit:

[0066]

[0067] Among them, 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. 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.

[0068] Compound A can be obtained from commercial purchase or preparation. Preferably, compound A can be prepared by the following method:

[0069] Provide compound C and compound D, described compound C has following structure:

[0070]

[0071] ...

Embodiment 1

[0106] Poly(N,N′-di-octyl-1,4,5,8-naphthalene tetracarboxylic acid diimide-3,7-bis(4-ethylthiophen-5-yl)-naphtho[1, Preparation of 2-c:5,6-c]bis[1,2,5]thiadiazole

[0107] (1) Preparation of N,N'-dioctyl-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid diimide (compound A).

[0108] 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 ).

[0109] 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) (15 mL) solution, reflux at 141°C for 12 hours. After cooling to room temperature, the reaction solution was poured into 10 mol / L sodium hydroxide aqueous 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 column. The solvent was re...

Embodiment 2

[0123] Poly(N,N′-bis-((1-octylnonyl))-1,4,5,8-naphthalene tetracarboxylic acid imide-4,8-bis(thiophen-2-yl)benzo[ Preparation of 1,2-c;4,5-c′]bis-[1,2,5]thiadiazole

[0124] (1) Preparation of N,N'-bis-(1-octylnonyl)-2,6-dibromo-1,4,5,8-naphthalene tetracarboxylic acid imide (Compound A)

[0125] Provide compound C and compound D, compound C is 2,6-dibromo-1,4,5,8-naphthalene dianhydride, compound D is 1-octyl-nonylamine;

[0126] 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) in propionic acid (15mL) solution, reflux at 141°C for 14 hours. After cooling to room temperature, the reaction solution was poured into 10 mol / L sodium hydroxide aqueous 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 column. The solvent was remov...

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Abstract

The invention relates to an organic semiconductor material containing naphtho-dithiadiazole and naphthalene tetracarboxylic diimide, and a preparation method and application of the organic semiconductor material. The organic semiconductor material containing naphtho-dithiadiazole and naphthalene tetracarboxylic diimide has the following structural formula as shown in the specification, wherein n is an integer in a range from 10 to 100; R1 is C1-C20 alkyl; R2, R3 and R4 are H, C1-C2 alkyls or C1-C20 alkoxy groups; R5 and R6 are H or C1-C20 alkyls. The organic semiconductor material containing naphtho-dithiadiazole and naphthalene tetracarboxylic diimide integrates advantages of naphtho-dithiadiazole and naphthalene tetracarboxylic diimide, has good charge transport performance, and can improve energy conversion efficiency of semiconductor devices when being used for the semiconductor devices, such as a solar battery.

Description

technical field [0001] The invention relates to the field of optoelectronic materials, in particular to an organic semiconductor material containing naphthobisthiadiazole and naphthalene tetracarboxylic diimide, a preparation method and application thereof. 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 ...

Claims

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Application Information

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