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Perylene diimide derivative, and preparation method and photoelectric device application thereof

A technology of perylene diimide and derivatives, which is applied in the field of optoelectronic device applications, perylene diimide derivatives and their preparation, can solve the problems of weak interaction force, affecting the optoelectronic properties of materials, etc., so as to reduce the steric position. resistance, enhancing intramolecular interactions, and excellent field effect performance

Pending Publication Date: 2021-10-29
XUZHOU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the large steric hindrance of the PDI structure unit, the intramolecular and intermolecular interactions of the molecules based on the PDI structural unit are easily weak, which affects the photoelectric performance of the material.

Method used

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  • Perylene diimide derivative, and preparation method and photoelectric device application thereof
  • Perylene diimide derivative, and preparation method and photoelectric device application thereof
  • Perylene diimide derivative, and preparation method and photoelectric device application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of Compound C-1

[0025]

[0026] Synthesis of compound C-1:

[0027] Compound C-1 was synthesized according to the general synthesis method described above, and the yield was 87%.

[0028] Elemental analysis: (C64H68N4O4) Theoretical value: C, 80.30; H, 7.16; N, 5.85; Found value: C, 80.34; H, 7.10; N, 5.86; HRMS (ESI) m / z (M+1) + : Theoretical value: 956.52; Measured value: 956.53.

Embodiment 2

[0030] Synthesis of compound C-2

[0031]

[0032] Compound C-2 synthesis:

[0033]

[0034] Compound C-2 was synthesized according to the general synthesis method described above, and the yield was 75%.

[0035] Elemental Analysis: (C60H64N4O4S2) Theoretical: C, 74.35; H, 6.66; N, 5.78; Found: C, 74.37; H, 6.61; N, 5.79; HRMS (ESI) m / z (M+1) + : Theoretical value: 968.43; measured value: 968.45.

Embodiment 3

[0037] Synthesis of Compound C-3

[0038]

[0039] Synthesis of compound C-3:

[0040]

[0041] Compound C-3 was synthesized according to the general synthesis method described above, and the yield was 78%.

[0042] Elemental Analysis: (C58H62N6O4S2) Theoretical: C, 71.72; H, 6.43; N, 8.65; Found: C, 71.70; H, 6.40; N, 8.71; HRMS (ESI) m / z (M+1) + : Theoretical value: 970.42; Measured value: 970.45.

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Abstract

The invention discloses a perylene diimide derivative, and a preparation method and a photoelectric device application thereof. Under the action of illumination and iodine, conjugate expansion of a bay position of perylene diimide and introduction of a bay position pyridine ring are achieved, delocalized electron cloud of molecules can be effectively expanded, and then performance improvement of a material in the photoelectric device is achieved. Meanwhile, the expansion of the perylene diimide bay site can effectively reduce the steric hindrance of the perylene diimide bay site, so that the intramolecular interaction between the perylene diimide structural unit and the Ar group is improved, the material is ensured to form effective pi-pi accumulation in the film, and the photoelectric property of the material is further improved. By changing an Ar structural unit, effective regulation and control of the characteristics such as absorption spectrum, fluorescence emission spectrum, band gap, energy level and the like of the molecules can be realized, so that the perylene diimide derivative can be widely applied to various photoelectric devices, and good application potential is embodied.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a perylene diimide derivative, a preparation method thereof and an application of a photoelectric device. Background technique [0002] Perylene diimide (PDI) has been used as an industrial pigment for hundreds of years. Due to its excellent thermal and chemical stability, PDI has been widely used as a dye in various industrial fields. In recent years, with the development of material science, PDI has been found to be an excellent building block of organic photoelectric functional materials. Organic molecules based on PDI structural units have been widely used in organic light-emitting diodes, organic field effect transistors, organic solar cells, Organic-inorganic hybrid perovskite solar cells and other fields reflect important research value and broad application prospects. However, due to the large steric hindrance of the PDI structure unit, the intramolecular and i...

Claims

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Application Information

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IPC IPC(8): C07D471/22C09K11/06H01L51/00H01L51/05H01L51/30
CPCC07D471/22C09K11/06C09K2211/1014C09K2211/1037C09K2211/1074C09K2211/1092C09K2211/1011H10K85/626H10K85/655H10K85/656H10K85/615H10K85/631H10K10/466H10K85/6572
Inventor 孙华王士凡董黎明堵锡华
Owner XUZHOU UNIV OF TECH
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