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Organic semiconductor material containing thiophene pyrrole dione unit and preparation method and application thereof

A thiophene pyrrole diketo, organic semiconductor technology, applied in the field of organic semiconductor materials, can solve problems such as low photoelectric conversion efficiency, and achieve the effects of improving photoelectric conversion efficiency, being easy to control, and being beneficial to film forming processing.

Active Publication Date: 2013-07-03
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 thiophene pyrrole dione unit and preparation method and application thereof
  • Organic semiconductor material containing thiophene pyrrole dione unit and preparation method and application thereof
  • Organic semiconductor material containing thiophene pyrrole dione unit and preparation method and application thereof

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Experimental program
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Effect test

preparation example Construction

[0032] The preparation method of the organic semiconductor material containing thienopyrrole diketone unit comprises the following steps:

[0033] Step S1: In an oxygen-free environment, the dithienothiophene compound (A 1 ) and n-butyllithium (n-BuLi) were added to the first solvent at a molar ratio of 1:2 to 1:4 at -100°C to -25°C to react for 0.5 to 5 hours, and then 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:

[0034]

[0035] Step S2: 5-alkylthiophene[3,4-c]-pyrrole-4,6-dione (A 2 ) and 1,3-dibromo-5-alkylthiophene [3,...

Embodiment 1

[0041] Embodiment 1. This embodiment discloses a copolymer with the following structure as an organic semiconductor material:

[0042]

[0043] In the above formula, n=20;

[0044] The preparation steps of above-mentioned copolymer are as follows:

[0045] One, the preparation of 4,4-dimethyl-2,6-bis(trimethyltin base)-4H-cyclopenta[2,1-b:3,4-b']dithiophene:

[0046]

[0047] At -100°C under nitrogen, add 20.00mL (2.00M) of n-butyllithium solution to 2.06g of 4,4-dimethyl-4H-cyclopenta[2,1-b:3,4- b'] In a reaction flask of dithiophene and 60 mL of tetrahydrofuran, after stirring for 1 hour, slowly add 7.74 g of trimethyltin chloride dropwise, return to room temperature, and continue stirring for 48 hours. After the reaction was completed, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, rotary evaporated, and recrystallized to obtain the product.

[0048] MALDI-TOF-MS (m / z): 531.9 (M + ).

[0049] Two, the pr...

Embodiment 2

[0061] Embodiment 2. This embodiment discloses a copolymer with the following structure as an organic semiconductor material:

[0062]

[0063] In the above formula, n=59;

[0064] The preparation steps of above-mentioned copolymer are as follows:

[0065] One, the preparation of 4,4-dioctyl-2,6-bis(trimethyltin base)-4H-cyclopenta[2,1-b:3,4-b']dithiophene:

[0066]

[0067] At -78°C under nitrogen, 20.00 mL (1.00 M) of n-butyllithium solution was added to 4.03 g of 4,4-dioctyl-4H-cyclopenta[2,1-b:3,4- b'] In a reaction flask of dithiophene and 70 mL of tetrahydrofuran, after stirring for 1 hour, slowly add 3.96 g of trimethyltin chloride dropwise, return to room temperature, and continue stirring for 32 hours. After the reaction was completed, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, rotary evaporated, and recrystallized to obtain the product.

[0068] MALDI-TOF-MS (m / z): 728.3 (M + ).

[0069] Two, ...

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Abstract

The invention belongs to the field of an optoelectronic material, and discloses an organic semiconductor material containing a thiophene pyrrole dione unit and a preparation method and an application thereof. The organic semiconductor material is shown in Formula (I), wherein R1, R2 and R3 are C1-C20 alkyl, and n is an integer more than 1 and less than or equal to 100. Compared with the prior art, the solubility and molecular weight of the product can be improved due to introduction of alkyl to realize the spin-coating polymer or spin-coating copolymer; and the polymer formed with thiophene pyrrole diketone monomers and thienothiophene monomers can achieve a strong donor-acceptor structure, thereby helping to improve the stability of the material and reduce the energy band gap of the material, expanding the scope of sunlight absorption, and improving the optoelectronic conversion efficiency.

Description

technical field [0001] The invention relates to an organic semiconductor material, in particular to an organic semiconductor material containing a thienopyrrole diketone unit. [0002] The invention also relates to a preparation method and application of an organic semiconductor material containing a thienopyrrole diketone unit. 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 directly convert sunlight energy into elect...

Claims

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Application Information

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