Carnegie Mellon University

Plextronics, Inc.

Solvay USA Inc.

Nissan Chemical Industries Limited

Nissan Chemical Corporation

Elena E Sheina

Richard D McCullough

Jinsong Liu

Paul C Ewbank

Christopher T Brown

Chad A Landis

Robert G Swisher

Darin W Laird

Venkataramanan Seshadri

Troy D Hammond

Christophe René Gaston Grenier

Shawn P Williams

Mihaela C Iovu

Ting Xu

Floryan De Campo

Brian Edward Woodworth

Jing Wang

Christopher Greco

Sergey B Li

Samuel M Mazza

Atta Gueye

Andrew W Hannah

Shijun Jia

Carolyn Skillman

Marc Sims

Chad Landis

Described herein are non-aqueous ink compositions containing a polythiophene having a repeating unit complying with formula (I) described herein, a transition metal complex having at least one &#x3b2;-diketonate ligand, and a liquid carrier having one or more organic solvents. The present disclosure also concerns the uses of such non-aqueous ink compositions, for example, in organic electronic devices.

Non-aqueous ink compositions containing transition metal complexes, and uses thereof in organic electronics

Described herein are compositions comprising hole carrier materials, typically conjugated polymers, and fluoropolymers ink compositions comprising hole carrier materials and fluoropolymers, and uses thereof, for example, in organic electronic devices.

Compositions containing hole carrier materials and fluoropolymers, and uses thereof

Described herein are non-aqueous ink compositions containing a sulfonated conjugated polymer, a polymeric acid, an optional matrix compound, and an amine compound. The present disclosure also concerns the uses of such non-aqueous ink compositions, for example, in organic electronic devices.

Non-aqueous compositions having sulfonated polythiophenes suitable for use in organic electronics

High performance organic photovoltaic cells based on donor acceptor polymers in the active layer. A composition comprising: at least one copolymer comprising at least one first donor moiety and at least one first acceptor moiety in the copolymer backbone, wherein the first acceptor moiety comprises at least one first ring which is bivalently linked to the copolymer backbone and at least one second ring fused to the first ring and not bivalently linked to the copolymer backbone, wherein the first ring or the second ring comprises two adjacent fluoro ring substituents, and optionally, wherein the donor comprises at least one fused ring system. High efficiency, high Voc, and a combination of both can be achieved.

Fluoro monomers, oligomers, and polymers for inks and organic electronic devices

Copolymers of 3,4-dialkoxythiophenes are disclosed that are useful as electronics materials. Also disclosed are methods of making these copolymers, as well as compositions and devices incorporating them. Use of these materials in hole injection or hole transport layers is disclosed. Materials comprising these copolymers can be designed to provide solubility in some solvents and intractability in others, which is useful for the construction of multilayer materials for use in electronic devices.

Copolymers of 3,4-dialkoxythiophenes and methods for making and devices

Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising: Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects. Polymers comprising benzodithiophene and/or benzothiadiazole structures can show particularly high performance.

Organic electronic devices and polymers, including photovoltaic cells and diketone-based polymers

An improved polymerization method including a method comprising providing a reaction mixture comprising a first monomer, an organic oxidant, and at least one Lewis acid or Br&#xf6;nsted acid, wherein the first monomer comprises at least one optionally substituted heterocyclic ring, wherein the heterocyclic ring comprises at least one heteroatom; and reacting the reaction mixture to obtain a conjugated polymer. The method can reduce the content of undesirable entities in the polymer such as halogens and metals, which can be useful in organic electronic device applications. Purification methods also are adapted to remove organic and inorganic impurities.

Synthesis of conjugated polymers via oxidative polymerization and related compositions

Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising: wherein A1 and A2 each independently comprise a fused ring system comprising at least two fused rings directly covalently linked to the pyrrole rings. Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects.

Organic electronic devices and polymers, including photovoltaic cells and diketone-based and diketopyrrolopyrrole-based polymers

A composition comprising a homopolymer or a copolymer comprising bithiophene units for use in, for example, low band gap materials including uses in organic photovoltaic active layers. The band gap and other properties can be engineered by polymerization methods including selection of monomer structure and ratio of monomer components. In addition, a dimer adapted for making alternating copolymers further comprising one first monomer moiety comprising at least one bithiophene moiety compound covalently linked to one second monomer moiety comprising a different bithiophene moiety or at least one moiety that is not a bithiophene. The composition can be copolymerized to form an alternating copolymer that can be further processed to form a polymeric film used in a printed organic electronic device. A series of novel copolymers are designed that would allow fabrication of materials with tailor made electronic and/or mechanical properties that can be easily manipulated through molecules chemical structure and potentially result in long term stability under ambient conditions that can be advantageous for use in organic electronics (e.g., OPVs, OLEDs, OFETs). Improved methods are disclosed for making monomers comprising a benzo[2,1-b:3,4-b']dithiophene moiety that are useful as electronics materials.

Compositions, methods and polymers

The present invention relates to polythiophenes, particularly regioregular head-to-tail poly(3-alkylthiophenes) (HT-PATs), block copolymers made therefrom, and their methods of formation. The present invention provides HT-PATs with well-defined, specific end-groups, functionalization of the defined HT-PATs, and incorporation of end group functionalized HT-PATs into block copolymers with structural polymers. The intrinsically conductive diblock and triblock copolymers, formed from the HT-PATs, have excellent conductivity and low polydispersities that are useful in a number of applications. The block copolymers of the present invention have been found to exhibit conductivities that range from a low of 10S/cm for certain applications to as high as several hundred S/cm or more.

Polythiophenes, block copolymers made therefrom, and methods of forming the same

Synthesis of regioregular thiophene-based polymers (PTs) and their functionalized counterparts via metal assisted cross-coupling polymerizations utilizing mixed halogen substituted aryl halide monomer precursors. The described method provides a means to control structural homogeneity and regioregularity and the electronic/spectroscopic properties of functionalized PTs, and leads to improved performance of organic semiconductor devices such as OPVs and/or OFETs. Asymmetrical monomers can be used.

Mixed halogen polymerization

Regioregular poly(3-alkylthiophenes) and other polythiophenes can be prepared by living polymerization which have good solubility, processability and environmental stability. The polymerization method can afford regioregular poly(3-alkylthiophenes) in high yields. Kinetic study of polymerization revealed the living character of this process. The molecular weight of poly(3-alkylthiophenes) is a function of the molar ratio of the monomer to nickel initiator, and conducting polymers with relatively narrow molecular weight distribution (PDI&#x3c;1.5) are now readily available. Sequential monomer addition resulted in new block copolymers containing different poly(3-alkylthiophene) segments, which further confirms the 'livingness' of this system. Other synthetic methods can be used as well to conduct living polymerization. Blends and electronic devices can be prepared.

Living synthesis of conducting polymers including regioregular polymers, polythiophenes, and block copolymers

Regioregular polythiophene polymers can be used in photovoltaic applications including copolymers and blends. The polymer can comprise heteroatoms in the side groups. Better efficiencies can be achieved.

Heteroatomic regioregular poly(3-substitutedthiophenes) for photovoltaic cells

Compositions for use in HIL/HTL applications include intrinsically conductive polymer, planarizing agent, and dopant, which are soluble in non-aqueous solvents. Block copolymers of regioregular alkyl/alkoxy- and aryl-substituted polythiophenes can be used. The compositions can be formed into thin films. Excellent efficiency and lifetime stability can be achieved.

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Pittsburgh, PA, United States of America

Elena E Sheina