Benzodithiophene copolymer containing isoindoline-1,3-dione unit and its preparation method and application

A technology of benzodithiophene and copolymers, which is applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., and can solve the problem of low photoelectric conversion efficiency

Active Publication Date: 2016-09-07
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

[0003] Although the energy conversion efficiency of organic solar cells has been greatly improved, 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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  • Benzodithiophene copolymer containing isoindoline-1,3-dione unit and its preparation method and application
  • Benzodithiophene copolymer containing isoindoline-1,3-dione unit and its preparation method and application
  • Benzodithiophene copolymer containing isoindoline-1,3-dione unit and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Embodiment 1. This embodiment discloses a benzodithiophene copolymer containing isoindoline-1,3-dione units with the following structure:

[0084]

[0085] Among them, R 1 , R 2 Same, both H; R 3 is octyloxy; R 4 for H; R 5 It is 16 alkyl groups, as shown in the figure, it is 2-hexyldecyl; n=60.

[0086] The preparation steps of the above-mentioned benzodithiophene copolymers containing isoindoline-1,3-dione units are as follows:

[0087] One, the preparation of 1,3-two (2-thiophene) acetone:

[0088]

[0089] First, dissolve 7.6 g, 36.8 mmol of DCC, 1.23 g, 10 mmol of DMAP in 70 mL of anhydrous dichloromethane, and dissolve 5 g, 35.2 mmol of 2-thiopheneacetic acid in 70 mL of dichloromethane under nitrogen protection. The methane solution was added dropwise to the above reaction solution and reacted overnight. After the reaction, the reaction solution was filtered, recrystallized twice with n-hexane, and then separated and purified by column chromatography...

Embodiment 2

[0110] Example 2. This example discloses a benzodithiophene copolymer containing isoindoline-1,3-dione units with the following structure:

[0111]

[0112] Among them, R 1 is hexyl; R 2 for H; R 3 For 2-methylthienyl; R 4 for H; R 5 is octyl, such as 1-n-octyl; n=55.

[0113] The above-mentioned preparation steps of the benzodithiophene copolymer containing isoindoline-1,3-diketone unit are as follows:

[0114] One, the preparation of two (4-dihexyl-2-thiophene) acetone:

[0115]

[0116] First, dissolve 7.6g of DCC and 1.23g of DMAP in 70mL of anhydrous dichloromethane, and add 7.6g of 4-hexyl-2-thiopheneacetic acid in 60mL of dichloromethane dropwise to the above-mentioned reaction solution overnight. After the reaction, the reaction solution was filtered, recrystallized twice with n-hexane, and then separated and purified by column chromatography to obtain the product.

[0117] MALDI-TOF-MS (m / z): 391 (M + ).

[0118] Two, 2,7-two (2-methyl-5-thiophene) ben...

Embodiment 3

[0134] Example 3. This example discloses a benzodithiophene copolymer containing isoindoline-1,3-dione units with the following structure:

[0135]

[0136] Among them, R 1 is 16 alkyl; R 2 for H; R 3 is methoxy; R 4 for H; R 5 is methyl; n=35.

[0137] 1. 2,5-dimethoxybenzene-7,9-bis(4-hexadecyl-5-trimethyltin-2-thiophene)-8H-cyclopentadienebenzo[1,2- b: Preparation of 4,3-b']dithiophen-8-one:

[0138]

[0139] For the synthesis method, refer to Step 1 to Step 4 in Example 1 above.

[0140] MALDI-TOF-MS (m / z): 1241 (M+ ).

[0141] Two, the preparation of the benzodithiophene copolymer containing isoindoline-1,3-dione unit:

[0142]

[0143] Under nitrogen protection, 0.74 g, 0.6 mmol of 2,5-dimethoxybenzene-7,9-bis(4-hexadecyl-5-trimethyltin-2-thiophene)-8H-cyclo Pentadienebenzo[1,2-b:4.3-b']dithiophen-8-one and 0.16g, 0.5mmol of 4,7-dibromo-2-methylisoindoline-1,3- Diketone was added to a reaction flask filled with 10 mL of dry DMF, and the reaction mixtur...

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Abstract

The present invention relates to a benzodithiophene based copolymer containing isoindoline-1,3-diketone units and a preparing method and applications thereof. The polymer has a structural formula (I), wherein R1 and R2 are respectively selected from H or alkyl groups of C1 to C16; R3 and R4 are respectively selected from H, alkyl groups of C1 to C16, alkoxy groups of C1 to C16, or thiophene groups substituted by alkyl groups of C1 to C16; R5 is selected from alkyl groups of C1 to C16; and n is a natural number of 7 to 80. Applications of the benzodithiophene based copolymer containing isoindoline-1,3-diketone units in polymer solar cells, polymer organic light-emitting, polymer organic field effect transistors, polymer organic optical storage, polymer organic nonlinear materials or polymer organic laser are also provided.

Description

【Technical field】 [0001] The invention relates to a benzodithiophene copolymer, in particular to a benzodithiophene copolymer containing an isoindoline-1,3-dione unit and a preparation method and application thereof. 【Background technique】 [0002] Organic solar cells have attracted widespread attention as a potential renewable energy source due to their incomparable advantages over inorganic solar cells, such as low cost, simple manufacturing process, light weight, and large-area flexible preparation. Over the past decade, the performance of organic solar cells has improved, with energy conversion efficiencies approaching 10%. [0003] Although the energy conversion efficiency of organic solar cells has been greatly improved, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells. Therefore, in order to realize the commercialization of organic solar cells, the development of new organic semiconductor ma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D495/00C09K11/06
Inventor 周明杰管榕李满园黄佳乐黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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