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Title: Fused thiophene-based conjugated polymers and their use in optoelectronic devices

Abstract

The present teachings relate to polymeric compounds and their use as organic semiconductors in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The disclosed compounds generally include as repeating units at least one annulated thienyl-vinylene-thienyl (TVT) unit and at least one other pi-conjugated unit. The annulated TVT unit can be represented by the formula: ##STR00001## where Cy.sup.1 and Cy.sup.2 can be a five- or six-membered carbocyclic ring. The annulated TVT unit can be optionally substituted at any available ring atom(s), and can be covalently linked to the other pi-conjugated unit via either the thiophene rings or the carbocyclic rings Cy.sup.1 and Cy.sup.2. The other pi-conjugated unit can be a conjugated linear linker including one or more unsaturated bonds, or a conjugated cyclic linker including one or more carbocyclic and/or heterocyclic rings.

Inventors:
; ; ; ;
Publication Date:
Research Org.:
Northwestern Univ., Evanston, IL (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1371756
Patent Number(s):
9,711,728
Application Number:
14/884,986
Assignee:
Northwestern University DOESC
DOE Contract Number:
SC0001059
Resource Type:
Patent
Resource Relation:
Patent File Date: 2015 Oct 16
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE

Citation Formats

Facchetti, Antonio, Marks, Tobin J., Takai, Atsuro, Seger, Mark, and Chen;, Zhihua. Fused thiophene-based conjugated polymers and their use in optoelectronic devices. United States: N. p., 2017. Web.
Facchetti, Antonio, Marks, Tobin J., Takai, Atsuro, Seger, Mark, & Chen;, Zhihua. Fused thiophene-based conjugated polymers and their use in optoelectronic devices. United States.
Facchetti, Antonio, Marks, Tobin J., Takai, Atsuro, Seger, Mark, and Chen;, Zhihua. Tue . "Fused thiophene-based conjugated polymers and their use in optoelectronic devices". United States. doi:. https://www.osti.gov/servlets/purl/1371756.
@article{osti_1371756,
title = {Fused thiophene-based conjugated polymers and their use in optoelectronic devices},
author = {Facchetti, Antonio and Marks, Tobin J. and Takai, Atsuro and Seger, Mark and Chen;, Zhihua},
abstractNote = {The present teachings relate to polymeric compounds and their use as organic semiconductors in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The disclosed compounds generally include as repeating units at least one annulated thienyl-vinylene-thienyl (TVT) unit and at least one other pi-conjugated unit. The annulated TVT unit can be represented by the formula: ##STR00001## where Cy.sup.1 and Cy.sup.2 can be a five- or six-membered carbocyclic ring. The annulated TVT unit can be optionally substituted at any available ring atom(s), and can be covalently linked to the other pi-conjugated unit via either the thiophene rings or the carbocyclic rings Cy.sup.1 and Cy.sup.2. The other pi-conjugated unit can be a conjugated linear linker including one or more unsaturated bonds, or a conjugated cyclic linker including one or more carbocyclic and/or heterocyclic rings.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Jul 18 00:00:00 EDT 2017},
month = {Tue Jul 18 00:00:00 EDT 2017}
}

Patent:

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  • The present teachings relate to certain polymeric compounds and their use as organic semiconductors in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The disclosed compounds can provide improved device performance, for example, as measured by power conversion efficiency, fill factor, open circuit voltage, field-effect mobility, on/off current ratios, and/or air stability when used in photovoltaic cells or transistors. The disclosed compounds can have good solubility in common solvents enabling device fabrication via solution processes.
  • The present invention relates to certain polymeric compounds and their use as organic semiconductors in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The present compounds can provide improved device performance, for example, as measured by power conversion efficiency, fill factor, open circuit voltage, field-effect mobility, on/off current ratios, and/or air stability when used in photovoltaic cells or transistors. The present compounds can have good solubility in common solvents enabling device fabrication via solution processes.
  • A regioselective synthesis of an azacoronene fused with two peripheral thiophene groups has been realized through a concise synthetic route. The resulting thienoazacoronene (TAC) derivatives show high degree of self-organization in solution, in single crystals, in the bulk, and in spuncast thin films. Spuncast thin film field-effect transistors of the TACs exhibited mobilities up to 0.028 cm.sup.2V.sup.-1 S.sup.-1, which is among the top field effect mobilities for solution processed discotic materials. Organic photovoltaic devices using TAC-containing conjugated polymers as the donor material exhibited a high open-circuit voltage of 0.89 V, which was ascribable to TAC's low-lying highest occupied molecular orbitalmore » energy level.« less
  • Resonant infrared matrix-assisted pulsed laser evaporation (RIR-MAPLE) is a variation of pulsed laser deposition that is useful for organic-based thin films because it reduces material degradation by selective absorption of infrared radiation in the host matrix. A unique emulsion-based RIR-MAPLE approach has been developed that reduces substrate exposure to solvents and provides controlled and repeatable organic thin film deposition. In order to establish emulsion-based RIR-MAPLE as a preferred deposition technique for conjugated polymer or hybrid nanocomposite optoelectronic devices, studies have been conducted to demonstrate the value added by the approach in comparison to traditional solution-based deposition techniques, and this workmore » will be reviewed. The control of hybrid nanocomposite thin film deposition, and the photoconductivity in such materials deposited using emulsion-based RIR-MAPLE, will also be reviewed. The overall result of these studies is the demonstration of emulsion-based RIR-MAPLE as a viable option for the fabrication of conjugated polymer and hybrid nanocomposite optoelectronic devices that could yield improved device performance.« less
  • Cross-conjugated donor-acceptor polymers, methods for their preparation, devices that include polymers, and methods for the preparation and use of the devices.