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Novel five-membered ring perylene diimide molecular material and its preparation method and application

An n-type, field-effect technology, applied in luminescent materials, chemical instruments and methods, electrical components, etc., can solve the problems of n-type semiconductor material research lag and lack of n-type materials, and achieve excellent electron transport performance and conjugation degree Big, good performance

Active Publication Date: 2021-11-02
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the study of n-type semiconductor materials is relatively lagging behind, and the mobility is greater than 1cm 2 V -1 the s -1 The n-type material is still lacking

Method used

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  • Novel five-membered ring perylene diimide molecular material and its preparation method and application
  • Novel five-membered ring perylene diimide molecular material and its preparation method and application
  • Novel five-membered ring perylene diimide molecular material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of compounds shown in embodiment 1, formula I and formula I' (in formula I, R 1 and R 2 Both are n-hexyl):

[0048] chemical reaction flow chart figure 1 Shown, concrete reaction step condition is as follows:

[0049] Add 30ml of thionyl chloride to compound 1 (2.94mmol), heat to 110° to react for 24h, and stop the reaction. The residual thionyl chloride was removed by a rotary evaporator to obtain compound 2. Then add aluminum chloride (9.64mmol) and 30ml of 1,2-dichlorobenzene to 2, stir at room temperature for 3min, then add hexyl isocyanate (44.1mmol), heat to 160°C for 24h, after the reaction stops, use column chromatography and heavy The crystallization method isolated the products PDI39 (0.439 mmol, yield: 15%) and PDI310 (0.382 mmol, yield: 13%);

[0050] The structural confirmation data are as follows:

[0051] Compound PDI39:

[0052] 1 H NMR (500MHz, CDCl 2 CDCl 2)δ (ppm): 8.96 (d, J = 8.5Hz, 2H), 8.57 (s, 2H), 8.51 (d, J = 7.5Hz, 2H), 7.8...

Embodiment 2

[0059] Crystal structure and packing of the compound shown in embodiment 2, formula I and formula I':

[0060] Preparation of crystals: Dissolve the compound in chloroform solution, and slowly diffuse methanol into the chloroform solution by diffusion method.

[0061] The crystal structure and packing of the compounds of the present invention are shown in figure 2 As shown, both isomers have good planarity. PDI310(b) exhibits a typical fishbone-like packing, with strong π-π interactions between molecules, and the π-π distance is PDI39(a) exhibits a two-dimensional stacking structure, and the intermolecular interactions are mainly hydrogen bond interactions and weaker π-π interactions. The π-π distance is similar to that of PDI310, and the distance between C-H…O is

Embodiment 3

[0062] The ultraviolet-visible absorption spectrum and fluorescence emission spectrum of the compound described in embodiment 3, formula I and formula I' in chloroform solution:

[0063] The compounds (compounds represented by formula I and formula I') prepared in Example 1 of the present invention are dissolved in various organic solvents, organic solvents include chloroform, o-dichlorobenzene, 1,1,2,2-tetrachloroethane alkanes, and other solvents such as toluene. The compounds of the invention have good solubility in chlorinated solvents. The solution absorption and emission spectra are measured by dissolving the compound shown in formula I and formula I' in chloroform solution as image 3 shown. Depend on image 3 It can be seen that the maximum absorption and emission wavelengths of PDI39 are 510nm and 530nm, respectively. Compared with PDI39, the absorption wavelength and emission of PDI310 are obviously red-shifted, which are 530nm and 556nm, respectively.

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Abstract

The invention discloses two kinds of five-membered ring perylene diimide molecular systems and its preparation method and its application in field effect transistor devices. The structural formula of the compound of the present invention is shown in formula I and formula I': in said formula I, R 1 and R 2 All are selected from any one of C6-C18 linear alkyl, phenyl, and 2,6-diisopropylphenyl, and R1 and R2 are the same. The heteroatom X is any one of an oxygen atom, a sulfur atom and a nitrogen atom. The invention provides a synthesis method of two five-membered ring perylene diimide isomers and its application in field effect transistors. Two kinds of five-membered ring perylene diimides were separated by two simple reactions, both of which exhibited n-type semiconductor properties, and the electron mobilities of PDI39 and PDI310 reached 0.0016 and 0.036 cm, respectively. 2 V ‑1 the s ‑1 , and the on-off ratios are greater than 10 6 .

Description

technical field [0001] The invention specifically relates to the development of a novel five-membered ring perylene diimide molecule, the development of a new preparation method and its application in field effect transistors, and belongs to the field of conjugated small molecule n-type semiconductor materials. Background technique [0002] As an important logic device, organic field effect transistors have important applications in flexible display, radio frequency identification, integrated circuits, electronic skin, memory storage, etc. Compared with non-field-effect transistors, organic field-effect transistors have attracted more and more researchers' attention due to their advantages of flexibility, light weight, and large-area fabrication. Organic semiconductors, as active layers in organic field-effect transistor devices, play a crucial role in their performance. In the past few decades, the research on p-type semiconductor materials has been relatively mature, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/06C09K11/06H01L51/05H01L51/30H01L51/40
CPCC07D487/06C09K11/06C09K2211/1044H10K71/164H10K10/46H10K85/6572
Inventor 张德清陈亮亮张西沙张关心刘子桐
Owner INST OF CHEM CHINESE ACAD OF SCI