Organic semiconductor material containing dithienothiophene and thienopyrryldiketone units, and preparation method and application thereof

A thiophenepyrrole diketo and organic semiconductor technology are applied in the preparation of organic semiconductor materials, in the field of organic semiconductor materials containing dithienothiophene and thiophenepyrrole dione units, which can solve problems such as low photoelectric conversion efficiency and improve photoelectric conversion. High efficiency, high yield and good electron delocalization performance

Inactive Publication Date: 2013-10-02
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells

Method used

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  • Organic semiconductor material containing dithienothiophene and thienopyrryldiketone units, and preparation method and application thereof
  • Organic semiconductor material containing dithienothiophene and thienopyrryldiketone units, and preparation method and application thereof
  • Organic semiconductor material containing dithienothiophene and thienopyrryldiketone units, and preparation method and application thereof

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Experimental program
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preparation example Construction

[0027] The preparation method of the organic semiconductor material containing dithienothiophene and thienopyrrole diketone unit comprises the following steps:

[0028] Step S1: In an oxygen-free environment, the dithienothiophene compound (A 1 ) and n-butyllithium (n-BuLi) are added to the first solvent at a molar ratio of 1:2 to 1:4 at -100°C to -25°C to react for 05. to 5 hours, and then add trimethyltin chloride (Me 3 SnCl, the amount of which is 2 to 4 times the molar weight of the dithienothiophene compound), and the reaction was continued for 24 to 48 hours to obtain the product, namely (3,5-dialkyldithieno[3,2-b;2 ',3'-d]thiophene-2,6-diyl)bis(trimethyltin)(B 1 ); wherein, the first solvent is at least one of tetrahydrofuran, ether, dichloromethane, chloroform or ethyl acetate, R 1 , R 2 same or different as C 1 -C 20 The alkyl group; Its reaction formula is as follows:

[0029]

[0030] Step S2: 5-alkylthiophene[3,4-c]-pyrrole-4,6-dione (A 2 ) and N-bromosu...

Embodiment 1

[0036] Embodiment 1. This embodiment discloses an organic semiconductor material with the following structure:

[0037]

[0038] In the above formula, n=20;

[0039] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0040] 1. Preparation of 3,5-dimethyldithieno[3,2-b; 2′,3′-d]thiophene-2,6-diyl-bis(trimethyltin):

[0041]

[0042] At -100°C, under the protection of argon, add 20.00mL (2.00M) n-butyllithium solution to 2.24g 3,5-dimethyldithieno[3,2-b;2′,3′ -d] In a reaction flask of thiophene and 100 mL of tetrahydrofuran, after stirring for 1 hour, slowly add 7.81 g of trimethyltin chloride dropwise, return to room temperature, and continue stirring for 48 hours. After the reaction, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, rotary evaporated, and recrystallized to obtain 3,5-dimethyldithieno[3,2-b;2′,3′-d] Thiophene-2,6-diyl-bis(trimethyltin) product.

[0043...

Embodiment 2

[0056] Embodiment 2. This embodiment discloses an organic semiconductor material with the following structure:

[0057]

[0058] In the above formula, n=42;

[0059] The preparation steps of the above-mentioned organic semiconductor material are as follows:

[0060] 1. Preparation of (3,5-dioctyldithieno[3,2-b; 2′,3′-d]thiophene-2,6-diyl)bis(trimethyltin):

[0061]

[0062] At -78°C under nitrogen, add 20.00mL (1.00M) of n-butyllithium solution to 4.21g of 3,5-dioctyldithieno[3,2-b;2′,3′-d ] in a reaction flask of thiophene and 100 mL of tetrahydrofuran, after stirring for 1 hour, slowly add 3.88 g of trimethyltin chloride dropwise, return to room temperature, and continue stirring for 38 hours. After the reaction, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, rotary evaporated, and recrystallized to obtain (3,5-dioctyldithieno[3,2-b; 2′,3′-d ]thiophene-2,6-diyl)bis(trimethyltin) product.

[0063] MALDI-TOF...

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Abstract

The invention belongs to the field of photoelectronic materials, and discloses an organic semiconductor material containing dithienothiophene and thienopyrryldiketone units, and a preparation method and application thereof. The organic semiconductor material has the following general formula (I), wherein R1, R2 and R3 are respectively a C1-C20 alkyl group, and n is a whole number which is greater than 1 and less than or equal to 100. Compared with the prior art, the alkyl group is introduced to enhance the solubility and molecular weight of the product, thereby implementing a spin coating polymer or spin coating oligomer. Since the polymer formed by the thienopyrryldiketone monomers and thienothiophene monomers can form a very strong donor-receptor structure, the stability of the material is enhanced, and the band gap of the material can be easily reduced, thereby widening the sunlight absorption range and enhancing the photoelectric conversion efficiency.

Description

technical field [0001] The invention relates to an organic semiconductor material, in particular to an organic semiconductor material containing dithienothiophene and thienopyrrole diketone units. [0002] The invention also relates to a preparation method and application of an organic semiconductor material containing dithienothiophene and thienopyrrole diketone units. Background technique [0003] Today's world economy is mainly based on fossil energy, such as coal, oil and natural gas. However, these non-renewable fossil energy sources are constantly being exhausted. Since the beginning of the 21st century, global energy issues and the ensuing environmental pollution and climate warming have become increasingly prominent and gradually intensified. Solar energy is considered to be one of the most promising renewable energy sources because of its widespread and vast distribution, large amount of resources, no pollution, cleanliness, safety, and easy access. Solar cells d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D519/00C09K11/06H01L51/30H01L51/46H01L51/54H01S5/36
CPCY02E10/549
Inventor 周明杰黄杰刘辉
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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