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Cyclic diketopyrrolopyrrole conjugated compounds as well as preparation method and application thereof

A technology of diketopyrrolopyrrole and diketopyrrolopyrrole, which is applied in the field of diketopyrrolopyrrole cyclic conjugated compounds, can solve the problems of no diketopyrrolopyrrole and no application, and achieve mild conditions and easy operation Easy, strong absorption effect

Inactive Publication Date: 2018-12-28
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently reported ring-mounted conjugated molecules are concentrated in biphenyl and acene ring molecules (J.Am.Chem.Soc.2017, 139, 18480-18483.; Science 2017, 356, 172-175.). The method of cyclic conjugated molecules has also not been applied to diketopyrrolopyrrole molecules, and no diketopyrrolopyrrole cyclic conjugated molecules have been reported.

Method used

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  • Cyclic diketopyrrolopyrrole conjugated compounds as well as preparation method and application thereof
  • Cyclic diketopyrrolopyrrole conjugated compounds as well as preparation method and application thereof
  • Cyclic diketopyrrolopyrrole conjugated compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The synthetic route of the diketopyrrolopyrrole cyclic conjugated molecule (referred to as C-DPP1) in this example is as follows:

[0058]

[0059] Concrete synthetic steps are:

[0060] (1) Into a reaction flask containing 850.4 mg of bistin-substituted diketopyrrolopyrrole 1 was added 374.2 mg of (1,5-cyclooctadiene)platinum(II) dichloride. Under nitrogen protection, inject 400ml of anhydrous tetrahydrofuran (THF), and stir at 70 degrees Celsius; after reacting for 12 hours, the product is cooled and spin-dried, and about 50ml of methanol is added, filtered, and the filter cake is placed in a vacuum drying oven at 50 degrees Celsius for 5 hours to obtain Product 2a.

[0061] (2) Add 554.4 mg of 1,1'-bis(diphenylphosphino)ferrocene (dppf) into the reaction flask containing the product 2a obtained in the above steps. Under the protection of nitrogen, inject 400ml of anhydrous dichloromethane, stir and react at room temperature for 12 hours, spin dry the product aft...

Embodiment 2

[0067] The synthesis route of the diketopyrrolopyrrole ring-conjugated molecule (referred to as C-DPP2) in this example is as follows:

[0068]

[0069] The specific synthesis steps are consistent with Example 1 of the present invention, the only difference is that the n-octyl-substituted 3 is used as the starting material, and the structure confirmation results of C-DPP2 are as follows: 1 H-NMR picture as Figure 4 as shown, 13 C-NMR picture as Figure 5 As shown, the mass spectrum is as Figure 6 shown.

Embodiment 3

[0071] Diketopyrrolopyrrole ring-conjugated molecular field-effect transistor devices:

[0072] The field effect transistor device structure is bottom gate-top contact, the specific structure is as follows Figure 7 As shown: the source and drain electrodes are all vapor-deposited gold layers with a thickness of 25nm, the gate electrode is silicon with a thickness of 400μm, the insulating layer is silicon dioxide modified with OTS (octadecyltrichlorosilane) with a thickness of 300nm, and the organic semiconductor part is C-DPP1 with a thickness of 40-60 nm.

[0073] Dissolve the diketopyrrolopyrrole cyclic conjugated molecule C-DPP1 obtained in Example 1 of the present invention as an active layer in a mixed solution of chloroform and n-hexane (volume ratio: 10:1), with a concentration of 10 mg / mL, using OTS (octadecyltrichlorosilane) modified silicon dioxide / silicon (SiO 2 / Si) substrate, as the organic semiconductor part of the organic field effect transistor device, the t...

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Abstract

The invention discloses cyclic diketopyrrolopyrrole conjugated compounds as well as a preparation method and an application thereof. The structural formula of the compounds are shown as formula I in the description, wherein in the formula I, each of R1 and R2 is one independently selected from hydrogen, C1-C50 straight-chain or branch-chain alkyl, C1-C50 straight-chain or branch-chain alkyl containing amido bonds, ether bonds and ester bonds and C1-C50 straight-chain or branch-chain perfluoroalkyl; each of R3 and R4 is one independently selected from substituted or non-substituted phenyl, thienyl, thiazolyl, pyridyl, quinolyl, furyl, pyrryl, imidazolyl, naphthyl and pyrenyl or a combined fragment of the groups linked by single bond, double bonds, triple bonds, oxygen, sulfur or nitrogen; nis an integer of 2-20. The synthesis steps are short, the conditions are mild, and the operation is simple; raw materials are convenient and easily available, and industrial production is easy; the compounds have good chemical stability, highly absorb visible light and are beneficial to inhibition of molecular aggregation, and a 3D charge transport channel is formed.

Description

technical field [0001] The invention relates to a diketopyrrolopyrrole cyclic conjugated compound and a preparation method and application thereof. Background technique [0002] Diketopyrrolopyrrole (Diketopyrrolopyrrole) compounds are an important organic optoelectronic material. This type of material is easy to synthesize and low in cost, has good photothermal stability, broad and strong absorption spectrum, and excellent crystallinity, so it is widely used in organic semiconductor devices, such as organic field effect transistors (Adv. Mater., 2016 , 28, 943-950.), organic solar cells (Acc. Chem. Res., 2016 49, 78-85.). However, all diketopyrrolopyrrole compounds so far are linear, star-shaped and other planar small molecules and polymers with particularly strong crystallinity. The appearance is not ideal; at the same time, the material has limited solubility in environmentally friendly low-boiling non-halogen solvents. These factors are not conducive to the large-scale...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/05H01L51/30H01L51/42H01L51/46H01L51/50H01L51/54
CPCC09K11/06C07F15/0086C09K2211/185H10K85/346H10K10/00H10K30/00H10K50/00Y02E10/549Y02P70/50
Inventor 李韦伟李诚
Owner INST OF CHEM CHINESE ACAD OF SCI
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