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Novel n type organic semiconductor material

A new type of alkyl technology, applied in the field of n-type organic semiconductor materials, can solve the problem that the performance of porphyrin-like acceptor materials is not very good

Inactive Publication Date: 2019-03-01
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, porphyrin compounds have been concentratedly designed as p-type donor materials, but n-type acceptor materials have been rarely reported, and the performance of the reported porphyrin class acceptor materials is not very good, and the PCE value is lower than 1% (W.T.Hadmojo , D.Yim, H.Aqoma, D.Y.Ryu, T.J.Shin, H.W.Kim, E.Hwang, W.D.Jang, I.H.Jung, S.Y.Jang, Artificial light-harvesting n-type porphyrin for panchromatic organic photovoltaic devices, Chem.Sci., 2017, August, 5095)
So far, there have been no literature or patent reports using the porphyrin unit as the core, the five-membered or six-membered aromatic ring as the bridging unit, and the electro-absorbing end group A connected to the β-position of the five-membered heterocycle or the six-membered heterocycle. A novel n-type acceptor material at the meta site of the ring

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] The synthetic route of the aldehyde compound containing fused ring unit and five-membered heterocycle is as follows:

[0091]

[0092] Add compound A (0.12mmol), compound B (0.3mmol) and 10mL of freshly steamed toluene into the reaction flask, evacuate nitrogen back and forth three times, add Pd(PPh 3 ) 4 (7.6mg), the temperature was 110°C, stirred for 48 hours; cooled to room temperature, added deionized water, CHCl 2 Extraction is carried out, and the obtained organic phase is dried with anhydrous magnesium sulfate; After filtering and spinning to remove the solvent, use petroleum ether / dichloromethane mixed solvent (volume ratio: 2:1) as eluting agent, silica gel (200-300 mesh) Column chromatography was used for separation and purification to obtain a yellow solid, which was molecule 1 containing a six-membered fused ring and an aldehyde group.

Embodiment 2

[0094] The synthetic route of the A-D-A type conjugated molecule containing fused ring unit is as follows:

[0095]

[0096] Add compound 1 (0.03mmol) and compound C (0.18mmol) and 10mL of distilled chloroform to the reaction flask, pass nitrogen for 30 minutes to remove the air in the reaction flask, then add piperidine, and stir at 65°C for 12 hours; cool to room temperature, pour the reaction solution into methanol, filter the obtained precipitate, use petroleum ether / dichloromethane mixed solvent as eluent, and conduct separation and purification on silica gel (200-300 mesh) column chromatography, which is the compound containing fused ring units. A-D-A type conjugated molecule 2.

Embodiment 3

[0098]

[0099] Add compound A (0.12mmol) and compound D (0.3mmol) and 10mL of freshly steamed toluene into the reaction flask, and add Pd(PPh 3 ) 4 (7.6mg), the temperature was 110°C, stirred for 48 hours; cooled to room temperature, added deionized water, CHCl 2 Extraction is carried out, and the obtained organic phase is dried with anhydrous magnesium sulfate; after filtering and spinning to remove the solvent, use petroleum ether / dichloromethane mixed solvent as eluent, and perform separation and purification by silica gel (200-300 mesh) column chromatography to obtain a solid The product, namely molecule 3, contains a five-membered fused ring and an aldehyde group.

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Abstract

The invention discloses a novel n type organic semiconductor material. The novel n type organic semiconductor material comprises five-parallel (six-parallel, seven-parallel or eleven-parallel) fused ring unit-based A-D-A type conjugated micromolecules and porphyrin micromolecules, wherein the five-parallel (six-parallel, seven-parallel or eleven-parallel) fused ring unit-based A-D-A type conjugated micromolecules are used for changing the position where a terminal electron-withdrawing group is linked with a penta aromatic heterocyclic ring according to structural characteristics of an A-D-A type receptor material, steric hindrance can be reduced, a material is enabled to have better steric configuration, and isotropic charge transmission can be favorably formed, so that the performance ofa device can be increased; the porphyrin micromolecules enable an electron-withdrawing terminal group A to be linked to a beta position of a penta heterocyclic ring or a meta position of a hepta heterocyclic ring according to the structure characteristics of a porphyrin compound, and better intermolecular charge transfer exists between a porphyrin core and the electron-withdrawing terminal group,so that the compound has better charge transmission performance; meanwhile, the steric hindrance can be reduced, and the material is enabled to have better steric configuration, so that the performance of the device can be increased.

Description

technical field [0001] The invention relates to a new type of n-type organic semiconductor material, including A-D-A type conjugated small molecules and porphyrin-based small molecules based on penta-(hexa-, hepta-, or undeca) condensed ring units. A-D-A type conjugated small molecules are small molecules with five (hexa, hepta, or undeca) fused ring units as the core, five-membered aromatic heterocycles as bridging units, and the electro-absorbing end group A connected to the five β-position of the membered heterocycle. Such molecules are used as active layer electron acceptor materials in organic solar cells, followed by field effect transistors and organic detectors. Porphyrin small molecules use the porphyrin unit as the core, and the five-membered or six-membered aromatic ring as the bridging unit. bit. Such molecules can be used as acceptor materials in organic solar cells. . Background technique [0002] With the increasingly prominent energy crisis and environme...

Claims

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Application Information

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IPC IPC(8): C07D495/22C07D495/04C07D487/22C07F7/08H01L51/50H01L51/54
CPCC07D487/22C07D495/04C07D495/22C07F7/0816C07F7/083H10K85/615H10K85/626H10K85/657H10K85/6576H10K85/6572H10K85/40H10K50/16
Inventor 孙丽雅徐云霄张阳黔
Owner NANJING UNIV OF TECH
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