Thiophene end groups of non-fullerene acceptors for electronic and photonic applications

A technology based on alkyl and atoms, applied in the field of OSC devices, can solve the problems of reduced extinction coefficient, poor short-circuit current density, weakened intramolecular charge transfer, etc.

Pending Publication Date: 2020-11-03
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

While the electron-rich thiophene ring weakens the intramolecular charge transfer (ICT) effect between the core and the terminal groups, which leads to blue-shifted absorption and a decrease in the acceptor extinction coefficient, and thus leads to poor short-circuit current density (JSC)

Method used

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  • Thiophene end groups of non-fullerene acceptors for electronic and photonic applications
  • Thiophene end groups of non-fullerene acceptors for electronic and photonic applications
  • Thiophene end groups of non-fullerene acceptors for electronic and photonic applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-C8-I

[0216] The synthetic route of embodiment 1-C8-ITCC-Cl

[0217] Step 1: Preparation of 5-chlorothiophene-2-carbonyl chloride

[0218]

[0219] 5-Chlorothiophene-2- carbon Synthesis of acid chlorides (B). To a solution of 5-chlorothiophene-2-carboxylic acid (A, 3.25 g, 20 mmol) in anhydrous dichloromethane (40 mL) was added chlorothiophene (40 mL, 1.0 M in dichloromethane). After stirring the mixture at room temperature overnight, dichloromethane and chlorinated thiophene were evaporated under reduced pressure. The resulting yellow solid was dried under high vacuum and used in the next step without further purification.

[0220] Step 2: Preparation of 2-chloro-4H-cyclopenta[b]thiophene-4,6(5H)-dione

[0221]

[0222] Synthesis of 2-chloro-4H-cyclopenta[b]thiophene-4,6(5H)-dione (C). Add anhydrous aluminum chloride (6.7 g, 50 mmol) and 5-chlorothiophene-2-carbonyl chloride (B) to anhydrous 1,2-dichloroethane (60 mL) under vigorous stirring in an ice bath Malonyl ...

Embodiment 2

[0229] Example 2 - Optical and Electrochemical Properties

Embodiment 2a

[0230] Example 2a: Optical properties

[0231] Thin film UV-Vis absorption spectra of the polymer from Example 2 were obtained on a Perkin Elmer Lambda 20 UV / VIS spectrophotometer. All film samples were spin-cast on ITO / ZnO substrates. The solution UV-Vis absorption spectrum under high temperature is collected on Perkin Elmer Lambda950UV / VIS / NIR spectrophotometer. The temperature of the cuvettes was controlled using a Perkin Elmer PTP 6+6 Peltier System supplied by a Perkin ElmerPCB 1500 Water Peltier System. Before each measurement, the system was kept at the target temperature for at least 10 min to reach thermal equilibrium. Stopped cuvettes (Sigma Z600628) were used to avoid volatilization during the measurement. The onset of absorption was used to estimate the polymer bandgap.

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Abstract

Provided herein are small molecular acceptor compounds containing thiophene end groups, methods for their preparation and intermediates used therein, the use of formulations containing the same as semiconductors in organic electronic devices, especially in organic photovoltaic and organic field-effect transistor devices, and to organic electronic and organic photovoltaic devices made from these formulations.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of priority to U.S. Provisional Application No. 62 / 920,446, filed May 1, 2019, the contents of which are hereby incorporated by reference in their entirety for all purposes. technical field [0003] The present disclosure relates to n-type organic semiconductors based on thiophene end groups, methods for their preparation and intermediates used therein, formulations containing such organic semiconductors as electron acceptors in organic solar cells (OSC) or other optoelectronic (OE) devices and OSC devices made from these formulations. Background technique [0004] Organic solar cells (OSCs) are considered as a promising low-cost and environmentally friendly solar technology because it can be produced using low-cost printing methods and does not contain any toxic components. [0005] Rapid progress in the development of novel electron-donating and electron-withdrawing building block...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22H01L51/42H01L51/46
CPCC07D495/22H10K85/6576H10K30/00Y02E10/549H10K85/113H10K85/151H10K30/30H10K30/20H10K30/65
Inventor 颜河张健全
Owner THE HONG KONG UNIV OF SCI & TECH
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