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Diketopyrrolopyrrole derivative and preparation method and application thereof

A technology of diketopyrrolopyrrole and derivatives is applied in the field of solar cell materials to achieve the effects of satisfying usage requirements, easy preparation method and high purity

Inactive Publication Date: 2013-05-08
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In 1986, Dr. Deng Qingyun of Kodak made a double-layer film composed of a derivative of tetracarboxyperylene and copper phthalocyanine, and connected the two layers of film to two electrodes to make an organic solar cell. The organic solar cell The photoelectric conversion efficiency reaches about 1%. Although it is far from inorganic solar cells, it is already a great breakthrough.

Method used

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  • Diketopyrrolopyrrole derivative and preparation method and application thereof
  • Diketopyrrolopyrrole derivative and preparation method and application thereof
  • Diketopyrrolopyrrole derivative and preparation method and application thereof

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Embodiment 1

[0066] Synthesis of Compound (II): Under argon protection, potassium tert-butoxide (20g, 180mmol) was added to a 250mL round-bottomed flask, and injected into a solution of 2-cyanothiophene (16.4g, 150mmol) in tert-amyl alcohol (125mL) , the reaction mixture was heated to 100-110° C., dimethyl succinate (7.30 g, 50 mmol) was dissolved in tert-amyl alcohol (40 mL), and added dropwise to the reaction solution. The reaction was kept at the same temperature, stirred for 1 h, and then the by-product methanol was distilled off, and the reaction was continued at 100-110° C. for 2 h. The reaction mixture was cooled to 65°C, diluted with 50 mL of methanol, neutralized with acetic acid, and then refluxed for 10 minutes. The reaction was stopped, filtered, and the obtained black solid was washed twice with hot methanol and water, and dried in a vacuum oven to obtain compound (II) (10.6 g, 72%).

Embodiment 2

[0068] Synthesis of compound (III): in a 250ml two-necked flask, under argon protection, compound (II) (13.0g, 43.3mmol) and anhydrous potassium carbonate (24g, 173mmol) were dissolved in 250mLN, N-dimethylformamide , heated to 145°C, injected octyl bromide (38.6g, 200mmol), and stirred at 145°C for 12h. Stop the reaction, cool to room temperature, pour the reaction solution into 500 mL of ice water, filter, wash the solid several times with water and methanol, and dry in a vacuum oven to obtain a crude product that is separated by silica gel column chromatography (dichloromethane as eluent) , to obtain dark red product compound (III) (18.18 g, 80%). 1 H NMR (400MHz, CDCl 3 ): δ8.94(dd, 2H), 7.65(dd, 2H), 7.29(dd, 2H), 4.08(t, 4H), 1.75(m, 4H), 1.18-1.48(m, 20H), 0.88( t, 6H).

Embodiment 3

[0070] Synthesis of Compound (IV): Compound (III) (5.25g, 10mmol) was dissolved in 200mL of chloroform, N-bromosuccinimide (NBS) (1.87g, 10.5mmol) was added in portions at room temperature, React at room temperature overnight in the dark. Pour the reaction solution into 200 mL of water, extract with chloroform, wash with water, combine the organic phases, dry over anhydrous magnesium sulfate, spin off the solvent to obtain a crude product, recrystallize from chloroform and ethanol to obtain a purple-black solid (3.80 g, 63%) .

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Abstract

The invention discloses a diketopyrrolopyrrole derivative. The structure of the diketopyrrolopyrrole derivative is as shown in a formula (I), wherein n=2 or 4, and R is selected from groups as shown in a formula (I-a), a formula (I-b) or a formula (I-c). The diketopyrrolopyrrole derivative disclosed by the invention achieves high absorbing capacity on visible light and can be applied to the field of organic solar energy as a micromolecular donator material. The invention also discloses a preparation method of the diketopyrrolopyrrole derivative. The diketopyrrolopyrrole derivative is obtained through a series of reaction, namely ring closing reaction, bromination reaction and coupling reaction, by taking 2-thiophenecarbonitrile and dimethyl succinate as initial raw materials.

Description

technical field [0001] The invention belongs to the technical field of solar cell materials, and in particular relates to a diketopyrrolopyrrole derivative and a preparation method and application thereof. Background technique [0002] Organic solar cells are a new type of solar cells under research. Compared with inorganic solar cells, they have the advantages of light weight, low price, solution processing, high mechanical flexibility, and can be made into flexible large-area devices. Dating back to 1958, Kearns and Calvin sandwiched the magnesium phthalocyanine dye layer between two electrodes with different work functions to support the first organic photoelectric conversion device, and observed an open circuit voltage of 200mV. Compared with inorganic solar cells, photoelectric The conversion efficiency is extremely low. In the two decades that followed, there was not much innovation in the field of organic solar cells. [0003] In 1986, Dr. Deng Qingyun of Kodak made...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07F7/08H01L51/46
CPCY02E10/549
Inventor 方俊锋叶丹丹张文俊胡钊闵超
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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