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Trifluoromethyl carbonyl isoindigo derivative and synthesis method for same

A technology of trifluoromethylcarbonylisoindigo and fluoromethylcarbonylisoindigo, which is applied in the field of trifluoromethylcarbonylisoindigo derivatives and their synthesis, and can solve the undiscovered synthesis report of trifluoromethylcarbonylisoindigo derivatives and other problems, to achieve the effect of lowering the LUMO energy level, simple synthesis method and high yield

Inactive Publication Date: 2013-03-27
HUZHOU TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no report on the application of small molecule derivatives of isoindigo to field effect transistors, nor is there any report on the synthesis of trifluoromethylcarbonyl isoindigo derivatives.

Method used

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  • Trifluoromethyl carbonyl isoindigo derivative and synthesis method for same
  • Trifluoromethyl carbonyl isoindigo derivative and synthesis method for same
  • Trifluoromethyl carbonyl isoindigo derivative and synthesis method for same

Examples

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Effect test

Embodiment 1

[0018] This example provides a soluble trifluoromethylcarbonyl isoindigo derivative, its structural formula is shown in Table 1, and its synthetic route can be found in figure 1 .

[0019] Table 1

[0020]

[0021] Preparation of compound M1

[0022] The synthetic method of described a kind of trifluoromethylcarbonyl isoindigo derivative (M1) comprises the steps:

[0023] (a) Synthesis of intermediate compound 4

[0024] The structural formula of intermediate compound 4 is:

[0025]

[0026] like figure 1 As shown, compound 4 was prepared by the literature method, and its detailed preparation method can be found in the literature "Mei, J.; Graham K.R.; Stalder, R.; Reynolds, J.R. Synthesis of Isoindigo-Based Oligothiophenes for Molecular Bulk Heterojunction Solar Cells, Org. Lett ., 4, 660-663(2010).》

[0027] (b) Synthesis of intermediate compound 5

[0028] The structural formula of intermediate compound 5 is:

[0029]

[0030] Its preparation method compri...

Embodiment 2

[0037] Embodiment 2, the ultraviolet absorption spectrum, electrochemical property, heat resistance of isoindigo derivative

[0038] figure 2 The ultraviolet absorption spectrum of isoindigo derivative M1 in chloroform and thin film is given, the maximum absorption peak position of its thin film is around 435nm, and the optical band gap is 1.91eV. image 3 The cyclic voltammetry curve of isoindigo derivative M1 is given. The cyclic voltammetry test is carried out on the computer-controlled CHI610D telephone line analyzer, using the traditional three-electrode test system, the platinum electrode is the working electrode, the silver / silver ion electrode is the reference electrode, and the electrolyte is tetra-n-butyl hexafluorophosphoric acid Ammonium in acetonitrile solution (0.1M), scan speed is 100mV / s, with ferrocene as reference. The oxidation potential of ferrocene measured under this system is 0.05eV, because the energy level of ferrocene under vacuum conditions is 4.8...

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Abstract

The invention relates to a trifluoromethyl carbonyl isoindigo derivative and a synthesis method for the same. The LUMO (lowest unoccupied molecular orbital) energy level of the compound is greatly lowered by introducing trifluoromethyl and carbonyl which strongly absorb electrons. The synthesis method for the compound is simple and high in reaction yield and has an application potential for organic field effect transistors. The structural formula of the compound prepared by the method is shown in the specification.

Description

technical field [0001] The invention relates to a low LUMO (lowest unoccupied orbital) energy level small molecule organic semiconductor material, in particular to a trifluoromethylcarbonyl isoindigo derivative and a synthesis method thereof. Background technique [0002] Organic Field Effect Transistors (OFETs) are the basic building blocks of organic circuits and one of the most important organic semiconductor devices. It has the advantages of being bendable, light in weight, low in cost and suitable for large-area preparation, and has important application prospects in many fields such as organic sensors, organic storage devices, flexible flat panel displays, electronic paper, and radio frequency identification. OFETs research has become an important field of frontier interdisciplinary research in chemistry, physics, materials science, electronics and informatics. "See literature: Klauk, H. Organic thin-film transistors, Chem. Soc. Rev. 39, 2643-2666 (2010)". Organic se...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14H01L51/30
Inventor 王坤燕唐培松曹枫陈海锋徐敏虹潘国祥
Owner HUZHOU TEACHERS COLLEGE
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