WO2012116017A3 - Polythiophene–fullerene conjugates for photovoltaic cells - Google Patents

Polythiophene–fullerene conjugates for photovoltaic cells Download PDF

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Publication number
WO2012116017A3
WO2012116017A3 PCT/US2012/026035 US2012026035W WO2012116017A3 WO 2012116017 A3 WO2012116017 A3 WO 2012116017A3 US 2012026035 W US2012026035 W US 2012026035W WO 2012116017 A3 WO2012116017 A3 WO 2012116017A3
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WO
WIPO (PCT)
Prior art keywords
polythiophene
fullerene
compositions
conjugates
photovoltaic cells
Prior art date
Application number
PCT/US2012/026035
Other languages
French (fr)
Other versions
WO2012116017A2 (en
Inventor
Reuben Rieke
Original Assignee
Rieke Metals Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rieke Metals Inc. filed Critical Rieke Metals Inc.
Publication of WO2012116017A2 publication Critical patent/WO2012116017A2/en
Publication of WO2012116017A3 publication Critical patent/WO2012116017A3/en

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/15—Nano-sized carbon materials
    • C01B32/152—Fullerenes
    • C01B32/156—After-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C08K3/045—Fullerenes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211—Fullerenes, e.g. C60
    • H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/141—Side-chains having aliphatic units
    • C08G2261/1412—Saturated aliphatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/142—Side-chains containing oxygen
    • C08G2261/1426—Side-chains containing oxygen containing carboxy groups (COOH) and/or -C(=O)O-moieties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/148—Side-chains having aromatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/90—Applications
    • C08G2261/91—Photovoltaic applications
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Abstract

Compositions suitable for manufacture of high-efficiency organic photovoltaic devices, and methods of preparing the compositions, are provided. Polythiophene-fullerene conjugates, wherein a conductive polythiophene polymer, such as a regioregular polythiophene, and a fullerene derivative, are constructed with defined spacing between the electron donor polythiophene and electron acceptor fullerene. Photovoltaic devices containing films including the inventive compositions can provide improved photoefficiencies for solar electrical generation with the flexible, relatively inexpensive, organic photovoltaic materials described herein.
PCT/US2012/026035 2011-02-24 2012-02-22 Polythiophene–fullerene conjugates for photovoltaic cells WO2012116017A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161446234P 2011-02-24 2011-02-24
US61/446,234 2011-02-24

Publications (2)

Publication Number Publication Date
WO2012116017A2 WO2012116017A2 (en) 2012-08-30
WO2012116017A3 true WO2012116017A3 (en) 2014-05-01

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WO (1) WO2012116017A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201522411A (en) * 2013-11-08 2015-06-16 Rieke Metals Inc Method of synthesis of polythiophenes of controlled molecular weight
KR101678294B1 (en) * 2014-02-05 2016-11-21 주식회사 엘지화학 Fullerene derivatives, organic solar cell using the same and fabricating method thereof
CN105669953B (en) * 2015-11-11 2018-03-30 南京工业大学 The exploitation and the application in organic solar batteries of electrons " binary channels " polymeric material
CN113444255B (en) * 2021-05-28 2022-06-14 云南大学 Imine covalent organic framework loaded fullerene C60 material, preparation method thereof and application of supercapacitor

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0546718A2 (en) * 1991-11-27 1993-06-16 Exxon Research And Engineering Company Synthesis of derivatized fullerenes
US5648523A (en) * 1995-10-26 1997-07-15 Chiang Long Y Fullerene derivatives as free-radical scavengers
US20060076050A1 (en) * 2004-09-24 2006-04-13 Plextronics, Inc. Heteroatomic regioregular poly(3-substitutedthiophenes) for photovoltaic cells
US7544747B2 (en) * 2004-06-02 2009-06-09 Konarka Technologies, Inc. Photoactive materials and related compounds, devices, and methods
US20090176994A1 (en) * 2007-12-21 2009-07-09 Laird Darin W Organic photovoltaic devices comprising fullerenes and derivatives thereof and improved methods of making fullerene derivatives
US20090215958A1 (en) * 2005-08-11 2009-08-27 Auckland Uniservices Limited Conducting polymers and uses thereof
US20100065834A1 (en) * 2008-09-16 2010-03-18 Plextronics, Inc. Integrated organic photovoltaic and light emitting diode device
US7781673B2 (en) * 2005-07-14 2010-08-24 Konarka Technologies, Inc. Polymers with low band gaps and high charge mobility
US20100311879A1 (en) * 2007-10-31 2010-12-09 Reike Metals Inc. Reverse addition process for preparation of regioregular conducting polymers

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0546718A2 (en) * 1991-11-27 1993-06-16 Exxon Research And Engineering Company Synthesis of derivatized fullerenes
US5648523A (en) * 1995-10-26 1997-07-15 Chiang Long Y Fullerene derivatives as free-radical scavengers
US7544747B2 (en) * 2004-06-02 2009-06-09 Konarka Technologies, Inc. Photoactive materials and related compounds, devices, and methods
US20060076050A1 (en) * 2004-09-24 2006-04-13 Plextronics, Inc. Heteroatomic regioregular poly(3-substitutedthiophenes) for photovoltaic cells
US7781673B2 (en) * 2005-07-14 2010-08-24 Konarka Technologies, Inc. Polymers with low band gaps and high charge mobility
US20090215958A1 (en) * 2005-08-11 2009-08-27 Auckland Uniservices Limited Conducting polymers and uses thereof
US20100311879A1 (en) * 2007-10-31 2010-12-09 Reike Metals Inc. Reverse addition process for preparation of regioregular conducting polymers
US20090176994A1 (en) * 2007-12-21 2009-07-09 Laird Darin W Organic photovoltaic devices comprising fullerenes and derivatives thereof and improved methods of making fullerene derivatives
US20100065834A1 (en) * 2008-09-16 2010-03-18 Plextronics, Inc. Integrated organic photovoltaic and light emitting diode device

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CRAVINO: "Conjugated polymers with tethered electron-accepting moieties as ambipolar materials for photovoltaics.", POLYM INT, vol. 56, no. 943?95, 28 February 2007 (2007-02-28), pages 943 *
KIM ET AL.: "A strong regioregularity effect in self-organizing conjugated polymer films and high- efficiency polythiophene:fullerene solar cells.", NATURE MATERIALS, 5 March 2006 (2006-03-05) *
LEE ET AL.: "Synthesis of C60-end capped P3HT and its application for high performance of P3HT/PCBM bulk heterojunction solar cells.", J. MATER. CHEM., vol. 20, no. 3287?3, May 2010 (2010-05-01), pages 3288 - 3290 *

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TW201238995A (en) 2012-10-01
WO2012116017A2 (en) 2012-08-30

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