US20130247989A1 - Inert solution-processable molecular chromophores for organic electronic devices - Google Patents

Inert solution-processable molecular chromophores for organic electronic devices Download PDF

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US20130247989A1
US20130247989A1 US13/800,396 US201313800396A US2013247989A1 US 20130247989 A1 US20130247989 A1 US 20130247989A1 US 201313800396 A US201313800396 A US 201313800396A US 2013247989 A1 US2013247989 A1 US 2013247989A1
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substituted
unsubstituted aryl
alkyl
heteroaryl groups
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Guillermo C. Bazan
Thomas S. Van Der Poll
Thuc-Quyen Nguyen
John Love
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University of California
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University of California
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Priority to US13/800,396 priority Critical patent/US20130247989A1/en
Priority to ES13715539T priority patent/ES2887212T3/es
Priority to PCT/US2013/033615 priority patent/WO2013142850A1/en
Priority to PL13715539T priority patent/PL2828902T3/pl
Priority to CN201380026203.1A priority patent/CN104321894B/zh
Priority to DK13715539.6T priority patent/DK2828902T3/da
Priority to EP13715539.6A priority patent/EP2828902B1/en
Publication of US20130247989A1 publication Critical patent/US20130247989A1/en
Assigned to ENERGY, UNITED STATES DEPARTMENT OF reassignment ENERGY, UNITED STATES DEPARTMENT OF CONFIRMATORY LICENSE (SEE DOCUMENT FOR DETAILS). Assignors: CALIFORNIA, UNIVERSITY OF
Assigned to THE REGENTS OF THE UNIVERSITY OF CALIFORNIA reassignment THE REGENTS OF THE UNIVERSITY OF CALIFORNIA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NGUYEN, THUC-QUYEN, LOVE, JOHN, VAN DER POLL, THOMAS S., BAZAN, GUILLERMO C.
Priority to US16/203,189 priority patent/US20190334094A1/en
Priority to US16/823,210 priority patent/US20210043845A1/en
Priority to US17/412,135 priority patent/US20220223797A1/en
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    • H01L51/0071
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D519/00Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/0803Compounds with Si-C or Si-Si linkages
    • C07F7/081Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • H01L51/42
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40Organosilicon compounds, e.g. TIPS pentacene
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/655Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/649Aromatic compounds comprising a hetero atom
    • H10K85/657Polycyclic condensed heteroaromatic hydrocarbons
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/30Organic 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
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50Photovoltaic [PV] devices
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211Fullerenes, e.g. C60
    • H10K85/215Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00Energy generation through renewable energy sources
    • Y02E10/50Photovoltaic [PV] energy
    • Y02E10/549Organic PV cells
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50Manufacturing or production processes characterised by the final manufactured product

Definitions

  • Small-molecule bulk-heterojunction (SM BHJ) solar cells have become a competitive alternative to the exhaustively studied polymer organic photovoltaics (OPV).
  • OOV polymer organic photovoltaics
  • Intense investigation into the design and utility of conjugated polymers for light harvesting has provided great insight into the design and implementation of organic semiconductors for OPV technology, to the point where power conversion efficiencies (PCEs) up to 8.4% have been achieved.
  • PCEs power conversion efficiencies
  • polymer systems inherently suffer from batch-to-batch variations and limited options for purification of the polymeric materials.
  • Small-molecule semiconductors avoid the drawbacks inherent to polymeric semiconductors, as they are monodisperse in nature and, due to having a higher solubility than polymeric analogs, can be purified and characterized using standard organic chemistry protocols.
  • HTL hole-transport layer
  • Molybdenum oxide is thermally evaporated onto devices, which prevents the use of inexpensive solution deposition during roll-to-roll manufacture. It would be preferable to use a solution-processable HTL material, such as poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate) (PEDOT:PSS), or other doped conjugated polymers.
  • PEDOT:PSS poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate)
  • PEDOT:PSS bears acidic protons, which, when deposited at an interface with the active layer, will protonate the pyridyl nitrogen of the pyridal[2,1,3]thiadiazole. This protonation results in a drastic reduction in the PCE of devices fabricated using PEDOT:PSS as the anode interlayer that use PT containing small molecule donors.
  • Other systems with labile protons and protonatable semiconductors will also lead to deterioration of power conversion efficiency.
  • the present invention is directed to organic non-polymeric chromophores containing the benzo[c][1,2,5]thiadiazole with an electron-withdrawing substituent W in the 5-position (5BTH), of the following structure:
  • R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
  • organic non-polymeric chromophores can be used in an electronic or optoelectronic device, for example, in the active layer of such a device.
  • W is F. In one embodiment, W is Cl. In one embodiment, W is Br. In one embodiment, W is I. In one embodiment, W is —CN. In one embodiment, W is —CF 3 . In one embodiment, W is —CHF 2 . In one embodiment, W is —CH 2 F.
  • the present invention is directed to organic non-polymeric chromophores containing the 5-fluorobenzo[c][1,2,5]thiadiazole (FBTH) structure:
  • R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl
  • heterojunction devices such as organic small molecule solar cells and transistors.
  • the present invention is directed to non-polymeric electron-donating and electron-accepting chromophores having a core structure of benzo[c][1,2,5]thiadiazole with an electron-withdrawing substituent W in the 5-position (5BTH), benzo[c][1,2,5]oxadiazole with an electron-withdrawing substituent W in the 5-position (5BO), or 2H-benzo[d][1,2,3]triazole (5BTR) with an electron-withdrawing substituent W in the 5-position (5BTR).
  • the present invention is directed to non-polymeric electron-donating and electron-accepting chromophores having a core structure of 5-fluorobenzo[c][1,2,5]thiadiazole (FBTH), 5-fluorobenzo[c][1,2,5]oxadiazole (FBO), or 5-fluoro-2H-benzo[d][1,2,3]triazole (FBTR) core structure.
  • FBTH 5-fluorobenzo[c][1,2,5]thiadiazole
  • FBO 5-fluorobenzo[c][1,2,5]oxadiazole
  • FBTR 5-fluoro-2H-benzo[d][1,2,3]triazole
  • the present invention is directed to optoelectronic devices comprising an active layer composition of a mixture of a non-polymeric light-harvesting electron-donating chromophore based on a 5BTH, 5BO, 5BTR, FBTH, FBO, or FBTR core structure with an electron-accepting material, such as a fullerene, methanofullerene, rylene diimides or related ⁇ -conjugated organic electron acceptors.
  • an electron-accepting material such as a fullerene, methanofullerene, rylene diimides or related ⁇ -conjugated organic electron acceptors.
  • Organic or inorganic electron acceptors can be used.
  • the present invention is directed to optoelectronic devices comprising an active layer composition of a mixture of a non-polymeric light-harvesting electron-accepting chromophore based on a 5BTH, 5BO, 5BTR, FBTH, FBO, or FBTR core structure with an electron-donating material.
  • Organic or inorganic electron donors can be used.
  • the present invention is also directed to methods of fabricating the devices by solution processing. In one embodiment, all active layers of the described optoelectronic devices are formed from solutions comprising of non-polymeric discrete organic materials.
  • the invention embraces compounds of Formula I:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • a 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • the invention embraces compounds of Formula II:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
  • n is an integer between 0 and 5, inclusive
  • a 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • n is an integer between 0 and 5, inclusive. In another embodiment, n is 0. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5.
  • X 1 and X 2 are each —C(W)— and Y 1 and Y 2 are each CH. In some embodiments of Formula II, X 1 and X 2 are each CH and Y 1 and Y 2 are each —C(W)—. In any of the foregoing embodiments, W can be F.
  • X 1 and X 2 are each —C(W)—, Y 1 and Y 2 are each CH and each M is S. In some embodiments of Formula II, X 1 and X 2 are each CH, Y 1 and Y 2 are each —C(W)—, and each M is S. In any of the foregoing embodiments, W can be F.
  • X 1 and X 2 are each —C(W)—, Y 1 and Y 2 are each CH and each M is O. In some embodiments of Formula II, X 1 and X 2 are each CH, Y 1 and Y 2 are each —C(W)—, and each M is O. In any of the foregoing embodiments, W can be F.
  • B 2 is selected from the group consisting of a nonentity, H, F, a C 1 -C 16 alkyl group, thiophene, benzothiophene, benzofuran, and benzothiazole.
  • B 2 is phenyl, substituted at the p-position with diphenylamine (i.e., the B 2 moiety is triphenylamine)
  • the invention embraces compounds of Formula II of Formula IIa, Formula IIb, Formula IIc, Formula IIa-F, Formula IIb-F, or Formula IIc-F:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in further embodiments, W is F;
  • n is an integer between 0 and 5, inclusive
  • a 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • n is an integer between 0 and 5, inclusive. In another embodiment, n is 0. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5.
  • each M is S.
  • each M is O.
  • each M is S.
  • each M is O.
  • each M is S.
  • each M is O.
  • each M is S.
  • each M is O.
  • each M is S.
  • each M is O.
  • each M is S.
  • each M is O.
  • the compounds of Formula II are selected from compounds of Formula IId:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in further embodiments, W is F;
  • n 0, 1, 2, or 3;
  • R 7 is selected from H, C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, benzofuran-2-yl, benzothiophene-2-yl, and benzothiazole-2-yl;
  • R 8 is selected from H, C 1 -C 16 alkyl or —O—C 1 -C 16 alkyl.
  • Q 1 is C.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)— and Y 1 and Y 2 are CH; in a further embodiment, W is F.
  • X 1 and X 2 are CH and Y 1 and Y 2 are —C(W)—; in a further embodiment, W is F.
  • n 2
  • R 7 is selected from H or C 1 -C 16 alkyl.
  • R 7 is selected from benzofuran-2-yl.
  • R 7 is selected from benzothiophene-2-yl.
  • R 7 is selected from benzothiazole-2-yl.
  • R 8 is selected from H or C 1 -C 16 alkyl.
  • R 8 is selected from C 1 -C 16 alkyl.
  • Q 1 is C, X 1 and X 2 are —C(W)—, and Y 1 and Y 2 are CH; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 1; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 1; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 1; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 1; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 1
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 1
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 1
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 1
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 1
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 1
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 1
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 1
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 2; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 2; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 2; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 2; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 2
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 2
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 2
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 2
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 2
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 2
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 2
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 2
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 3; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 3
  • W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 3; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 3
  • W is F
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 3
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 3
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 3
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 3
  • R 7 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 3
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 3
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 3
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 3
  • R 8 is 2-ethyl-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 3
  • R 8 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is C
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 3
  • R 8 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are —C(W)—
  • Y 1 and Y 2 are CH
  • n is 3
  • R 8 is n-hexyl; in a further embodiment of this type, W is F.
  • Q 1 is Si
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 3
  • R 8 is n-hexyl; in a further embodiment of this type, W is F.
  • the compound is of the formula:
  • the compound is of the formula:
  • the compound is of the formula:
  • the compound is of the formula:
  • the compound is of the formula:
  • the compound is of the formula:
  • the compound is of the formula:
  • the compound is of the formula:
  • the compound is of the formula:
  • the compound is of the formula:
  • the compound is of the formula:
  • the compounds are of Formula IIe:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F;
  • n 0, 1, 2, or 3;
  • R 7 is selected from H, C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, benzofuran-2-yl, benzothiophene-2-yl, benzothiazole-2-yl, 4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl, 4,4-bis(C 1 -C 16 alkyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl, and 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl; and
  • R 9 is selected from H, C 1 -C 16 alkyl or —O—C 1 -C 16 alkyl. In a further embodiment of this type, W is F.
  • n 0.
  • n 1
  • n 2
  • n 3.
  • X 1 and X 2 are —C(W)— and Y 1 and Y 2 are CH; in a further embodiment of this type, W is F.
  • X 1 and X 2 are CH and Y 1 and Y 2 are —C(W)—; in a further embodiment of this type, W is F.
  • R 9 is —O—C 1 -C 16 alkyl.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ).
  • R 7 is 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ) and R 7 is 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl.
  • R 9 is —O—C 1 -C 16 alkyl and n is 0.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ) and n is 0.
  • R 7 is 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl and n is 0.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ), R 7 is 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl and n is 0.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 )
  • R 7 is 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl
  • X 1 and X 2 are —C(W)—
  • Y 2 are CH; in a further embodiment of this type, W is F.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ),
  • R 7 is 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl,
  • X 1 and X 2 are CH, and
  • Y 1 and Y 2 are —C(W)—; in a further embodiment of this type, W is F.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ),
  • R 7 is 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl,
  • X 1 and X 2 are —C(W)—,
  • Y 1 and Y 2 are CH, and
  • n is 0; in a further embodiment of this type, W is F.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ),
  • R 7 is 4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b′]dithiophene-2-yl
  • X 1 and X 2 are CH
  • Y 1 and Y 2 are —C(W)—
  • n is 0; in a further embodiment of this type, W is F.
  • R 7 is n-hexyl
  • R 9 is —O—C 1 -C 16 alkyl and n is 1.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ) and n is 1.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ) and R 7 is n-hexyl.
  • R 7 is n-hexyl and n is 1.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ), R 7 is n-hexyl and n is 1.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ), R 7 is n-hexyl, X 1 and X 2 are —C(W)—, and Y 1 and Y 2 are CH; in a further embodiment of this type, W is F.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ), R 7 is n-hexyl, X 1 and X 2 are CH, and Y 1 and Y 2 are —C(W)—; in a further embodiment of this type, W is F.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ), R 7 is n-hexyl, X 1 and X 2 are —C(W)—, Y 1 and Y 2 are CH, and n is 1; in a further embodiment of this type, W is F.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ), R 7 is n-hexyl, X 1 and X 2 are CH, Y 1 and Y 2 are —C(W)—, and n is 1; in a further embodiment of this type, W is F.
  • the compounds of Formula II embrace compounds of Formula IIf:
  • R 9 is H, C 1 -C 16 alkyl or —O—C 1 -C 16 alkyl, and where W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F. In a further embodiment, W is F.
  • R 9 is —O—CH 2 CH(C 2 H 5 )(C 4 H 9 ).
  • R 9 is —O—(CH 2 ) 5 CH 3 .
  • the invention embraces compounds of Formula III:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F (Formula III-F);
  • H 1 is selected from A 1 , —B 1 —B 2 , -A 1 -B 1 —B 2 , or
  • n is an integer between 0 and 5, inclusive
  • a 1 (when present) is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 1 (when present) is independently selected from substituted or unsubstituted aryl or heteroaryl groups such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 2 (when present) is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • n is an integer between 0 and 5, inclusive. In another embodiment, n is 0. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5.
  • the invention embraces compounds of Formula III of Formula IIIa, Formula IIIb, Formula IIIc, and Formula IIId:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F (Formula IIIa-F, Formula IIIb-F, Formula IIIc-F, or Formula IIId-F);
  • n is an integer between 0 and 5, inclusive
  • a 1 (when present) is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 1 (when present) is independently selected from substituted or unsubstituted aryl or heteroaryl groups such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • Such groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole, benzothiazole
  • each B 2 (when present) is independently selected from a nonentity, H, F, a C 1 -C 10 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • n is an integer between 0 and 5, inclusive. In another embodiment, n is 0. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5.
  • the invention embraces compounds of Formula IV-V:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F;
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • K 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each E 1 is independently either absent, or selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each M is S.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • each M is S, each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • X 1 , X 2 , and X 3 are each —C(W)— and Y 1 , Y 2 , and Y 3 , are each CH. In some embodiments of Formula IV-V, X 1 , X 2 , and X 3 are each CH and Y 1 , Y 2 , and Y 3 are each —C(W)—.
  • X 1 , X 2 , and X 3 are each —C(W)— and Y 1 , Y 2 , and Y 3 , are each CH, and each M is S.
  • X 1 , X 2 , and X 3 are each CH and Y 1 , Y 2 , and Y 3 are each —C(W)—, and each M is S.
  • X 1 , X 2 , and X 3 are each —C(W)— and Y 1 , Y 2 , and Y 3 , are each CH, and each M is O.
  • X 1 , X 2 , and X 3 are each CH and Y 1 , Y 2 , and Y 3 are each —C(W)—, and each M is O.
  • the invention embraces compounds of Formula IV-V of Formula IV:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F;
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • K 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each M is S.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • each M is S, each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • X 1 , X 2 , and X 3 are each —C(W)— and Y 1 , Y 2 , and Y 3 , are each CH; in further embodiments of this type, W is F.
  • X 1 , X 2 , and X 3 are each CH and Y 1 , Y 2 , and Y 3 are each —C(W)—; in further embodiments of this type, W is F.
  • X 1 , X 2 , and X 3 are each —C(W)— and Y 1 , Y 2 , and Y 3 , are each CH, and each M is S; in further embodiments of this type, W is F.
  • X 1 , X 2 , and X 3 are each CH and Y 1 , Y 2 , and Y 3 are each —C(W)—, and each M is S; in further embodiments of this type, W is F.
  • X 1 , X 2 , and X 3 are each —C(W)— and Y 1 , Y 2 , and Y 3 , are each CH, and each M is O; in further embodiments of this type, W is F.
  • X 1 , X 2 , and X 3 are each CH and Y 1 , Y 2 , and Y 3 are each —C(W)—, and each M is O; in further embodiments of this type, W is F.
  • the invention embraces compounds of Formula IV of Formula IVa or Formula IVb:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F (Formula IVa-F or Formula IVb-F);
  • K 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each M is S.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • each M is S, each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • W can be F.
  • each M is O.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • each M is O, each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • W can be F.
  • each M is S.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • each M is S, each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • W can be F.
  • each M is O.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • each M is O, each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • W can be F.
  • the invention embraces compounds of Formula IV-V of Formula V:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—;
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F;
  • K 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D 1 and E 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each M is S.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • each M is S, each D 1 is the same moiety, and each D 2 is the same moiety (independently of D 1 ).
  • W can be F.
  • X 1 , X 2 , and X 3 are each —C(W)— and Y 1 , Y 2 , and Y 3 , are each CH. In some embodiments of Formula V, X 1 , X 2 , and X 3 are each CH and Y 1 , Y 2 , and Y 3 are each —C(W)—. In any of the foregoing embodiments, W can be F.
  • X 1 , X 2 , and X 3 are each —C(W)— and Y 1 , Y 2 , and Y 3 , are each CH, and each M is S.
  • X 1 , X 2 , and X 3 are each CH and Y 1 , Y 2 , and Y 3 are each —C(W)—, and each M is S.
  • W can be F.
  • X 1 , X 2 , and X 3 are each —C(W)— and Y 1 , Y 2 , and Y 3 , are each CH, and each M is O.
  • X 1 , X 2 , and X 3 are each CH and Y 1 , Y 2 , and Y 3 are each —C(W)—, and each M is O.
  • W can be F.
  • the invention embraces compounds of Formula Va or Formula Vb:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F (Formula Va-F or Formula Vb-F);
  • K 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D 1 and E 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each D2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl and heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, pyrimidine, pyrazine, imidazole, benzoxazole, benzoxadiazole
  • each M is S.
  • each E 1 is the same moiety.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each E 1 is the same moiety, each D 1 is the same moiety, and each D 2 is the same moiety (where E 1 , D 1 , and D 2 are chosen independently of each other).
  • each M is S, and each E 1 is the same moiety, each D 1 is the same moiety, and each D 2 is the same moiety (where E 1 , D 1 , and D 2 are chosen independently of each other).
  • W can be F.
  • each M is O.
  • each E 1 is the same moiety.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each E 1 is the same moiety, each D 1 is the same moiety, and each D 2 is the same moiety (where E 1 , D 1 , and D 2 are chosen independently of each other).
  • each M is O, and each E 1 is the same moiety, each D 1 is the same moiety, and each D 2 is the same moiety (where E 1 , D 1 , and D 2 are chosen independently of each other).
  • W can be F.
  • each M is S.
  • each E 1 is the same moiety.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each E 1 is the same moiety, each D 1 is the same moiety, and each D 2 is the same moiety (where E 1 , D 1 , and D 2 are chosen independently of each other).
  • each M is S, and each E 1 is the same moiety, each D 1 is the same moiety, and each D 2 is the same moiety (where E 1 , D 1 , and D 2 are chosen independently of each other).
  • W can be F.
  • each M is O.
  • each E 1 is the same moiety.
  • each D 1 is the same moiety.
  • each D 2 is the same moiety.
  • each E 1 is the same moiety, each D 1 is the same moiety, and each D 2 is the same moiety (where E 1 , D 1 , and D 2 are chosen independently of each other).
  • each M is O, and each E 1 is the same moiety, each D 1 is the same moiety, and each D 2 is the same moiety (where E 1 , D 1 , and D 2 are chosen independently of each other).
  • W can be F.
  • the invention embraces compounds of Formula VI-VII:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , Y 2 , X 3 , and Y 3
  • M is selected from sulfur (S), oxygen (O), or N—R 19 where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F;
  • each F 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each M is S. In other embodiments of Formula VI-VII, each M is O.
  • X 1 , X 2 , X 3 , and X 4 are each —C(W)— and Y 1 , Y 2 , Y 3 , and Y 4 are each CH.
  • X 1 , X 2 , X 3 , and X 4 are each CH and Y 1 , Y 2 , Y 3 , and Y 4 are each —C(W)—.
  • W can be F.
  • X 1 , X 2 , X 3 , and X 4 are each —C(W)— and Y 1 , Y 2 , Y 3 , and Y 4 are each CH, and each M is S.
  • X 1 , X 2 , X 3 , and X 4 are each CH and Y 1 , Y 2 , Y 3 , and Y 4 are each —C(W)—, and each M is S.
  • W can be F.
  • X 1 , X 2 , X 3 , and X 4 are each —C(W)— and Y 1 , Y 2 , Y 3 , and Y 4 are each CH, and each M is O.
  • X 1 , X 2 , X 3 , and X 4 are each CH and Y 1 , Y 2 , Y 3 , and Y 4 are each —C(W)—, and each M is O.
  • W can be F.
  • each F 1 is the same moiety. In some embodiments of Formula VI-VII, each G 1 is the same moiety. In some embodiments of Formula VI-VII, each G 2 is the same moiety. In some embodiments of Formula VI-VII, each F 1 is the same moiety, each G 1 is the same moiety, and each G 2 is the same moiety (where F 1 , G 1 , and G 2 are chosen independently of each other). In some embodiments of Formula VI-VII, each F 1 is the same moiety, each G 1 is the same moiety, and each G 2 is the same moiety (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is S. In some embodiments of Formula VI-VII, each F 1 is the same moiety, each G 1 is the same moiety, and each G 2 is the same moiety (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is O.
  • the invention embraces compounds of Formula VI:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , Y 2 , X 3 , and Y 3
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F;
  • each F 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each M is S. In other embodiments of Formula VI, each M is O.
  • X 1 , X 2 , X 3 , and X 4 are each —C(W)— and Y 1 , Y 2 , Y 3 , and Y 4 are each CH. In some embodiments of Formula VI, X 1 , X 2 , X 3 , and X 4 are each CH and Y 1 , Y 2 , Y 3 , and Y 4 are each —C(W)—. In any of the foregoing embodiments, W can be F.
  • X 1 , X 2 , X 3 , and X 4 are each —C(W)— and Y 1 , Y 2 , Y 3 , and Y 4 are each CH, and each M is S.
  • X 1 , X 2 , X 3 , and X 4 are each CH and Y 1 , Y 2 , Y 3 , and Y 4 are each —C(W)—, and each M is S.
  • W can be F.
  • X 1 , X 2 , X 3 , and X 4 are each —C(W)— and Y 1 , Y 2 , Y 3 , and Y 4 are each CH, and each M is O.
  • X 1 , X 2 , X 3 , and X 4 are each CH and Y 1 , Y 2 , Y 3 , and Y 4 are each —C(W)—, and each M is O.
  • W can be F.
  • each F 1 is the same. In some embodiments of Formula VI, each G 1 is the same. In some embodiments of Formula VI, each G 2 is the same. In some embodiments of Formula VI, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other). In some embodiments of Formula VI, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is S. In some embodiments of Formula VI, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is O.
  • the invention embraces compounds of Formula VI, such as compounds of Formula VIa or Formula VIb:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F (fluorine) (Formula VIa-F or Formula VIb-F);
  • each F 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each M is S. In other embodiments of Formula VIa, each M is O. In some embodiments of Formula VIa, each F 1 is the same. In some embodiments of Formula VIa, each G 1 is the same. In some embodiments of Formula VIa, each G 2 is the same. In some embodiments of Formula VIa, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other). In some embodiments of Formula VIa, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is S.
  • each F 1 is the same, each G 1 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other), and each G 2 is the same; and M is O.
  • W can be F (fluorine).
  • each M is S. In other embodiments of Formula VIb, each M is O. In some embodiments of Formula VIb, each F 1 is the same. In some embodiments of Formula VIb, each G 1 is the same. In some embodiments of Formula VIb, each G 2 is the same. In some embodiments of Formula VIb, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other). In some embodiments of Formula VIb, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is S.
  • each F 1 is the same, each G 1 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other), and each G 2 is the same; and M is O.
  • W can be F (fluorine).
  • the invention embraces compounds of Formula VII:
  • X 1 and Y 1 are selected from —C(W)— and CH, where when X 1 is —C(W)—, Y 1 is CH, and when X 1 is CH, Y 1 is —C(W)—; and where, independently of X 1 and Y 1 , X 2 and Y 2 are selected from —C(W)— and CH, where when X 2 is —C(W)—, Y 2 is CH, and when X 2 is CH, Y 2 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , and Y 2 , X 3 and Y 3 are selected from —C(W)— and CH, where when X 3 is —C(W)—, Y 3 is CH, and when X 3 is CH, Y 3 is —C(W)—; and where, independently of X 1 , Y 1 , X 2 , Y 2 , X 3 , and Y 3
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F (fluorine);
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • each F 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each M is S. In other embodiments of Formula VII, each M is O.
  • X 1 , X 2 , X 3 , and X 4 are each —C(W)— and Y 1 , Y 2 , Y 3 , and Y 4 are each CH. In some embodiments of Formula VII, X 1 , X 2 , X 3 , and X 4 are each CH and Y 1 , Y 2 , Y 3 , and Y 4 are each —C(W)—. In any of the foregoing embodiments, W can be F (fluorine).
  • X 1 , X 2 , X 3 , and X 4 are each —C(W)— and Y 1 , Y 2 , Y 3 , and Y 4 are each CH, and each M is S.
  • X 1 , X 2 , X 3 , and X 4 are each CH and Y 1 , Y 2 , Y 3 , and Y 4 are each —C(W)—, and each M is S.
  • W can be F (fluorine).
  • X 1 , X 2 , X 3 , and X 4 are each —C(W)— and Y 1 , Y 2 , Y 3 , and Y 4 are each CH, and each M is O.
  • X 1 , X 2 , X 3 , and X 4 are each CH and Y 1 , Y 2 , Y 3 , and Y 4 are each —C(W)—, and each M is O.
  • W can be F (fluorine).
  • each F 1 is the same. In some embodiments of Formula VII, each G 1 is the same. In some embodiments of Formula VII, each G 2 is the same. In some embodiments of Formula VII, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other). In some embodiments of Formula VII, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is S. In some embodiments of Formula VII, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is O.
  • the invention embraces compounds of Formula VII, such as compounds of Formula VIIa or Formula VIIb:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F (fluorine) (Formula VIIa-F or Formula VIIb-F);
  • each F 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 1 is independently selected from substituted or unsubstituted aryl or heteroaryl groups, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each G 2 is independently selected from a nonentity, H, F, a C 1 -C 16 alkyl group, or a substituted or unsubstituted aryl or heteroaryl group, such as C 6 -C 30 substituted or unsubstituted aryl or heteroaryl groups, C 6 -C 20 substituted or unsubstituted aryl or heteroaryl groups, and C 6 -C 10 substituted or unsubstituted aryl or heteroaryl groups.
  • aryl or heteroaryl groups include, but are not limited to, thiophene, pyrrole, furan, phenyl, phosphole, benzodithiophene, spirofluorene, spirothiophene, bithiophene, terthiophene, thienothiophene, dithienothiophene, benzothiophene, isobenzothiophene, benzodithiophene, cyclopentadithiophene, silacyclopentadiene, silacyclopentadienebithiophene, indole, benzene, naphthalene, anthracene, perylene, indene, fluorene, pyrene, azulene, pyridine, oxazole, thiazole, thiazine, thiazolyl, pyrimidine, pyrazine, imidazole, benzoxazole,
  • each M is S. In other embodiments of Formula VIIa, each M is O. In some embodiments of Formula VIIa, each F 1 is the same. In some embodiments of Formula VIIa, each G 1 is the same. In some embodiments of Formula VIIa, each G 2 is the same. In some embodiments of Formula VIIa, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where G 1 and G 2 are chosen independently of each other). In some embodiments of Formula VIIa, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is S.
  • each F 1 is the same, each G 1 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other), and each G 2 is the same; and M is O.
  • W can be F (fluorine).
  • each M is S. In other embodiments of Formula VIIb, each M is O. In some embodiments of Formula VIIb, each F 1 is the same. In some embodiments of Formula VIIb, each G 1 is the same. In some embodiments of Formula VIIb, each G 2 is the same. In some embodiments of Formula VIIb, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other). In some embodiments of Formula VIIb, each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is S.
  • each F 1 is the same, each G 1 is the same, and each G 2 is the same (where F 1 , G 1 , and G 2 are chosen independently of each other); and M is O.
  • W can be F (fluorine).
  • the invention embraces compounds of Formula 1-2-3-4-5:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F;
  • n is an integer from 0 to 5 inclusive
  • R 2 is selected from H, C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, C 2 -C 16 alkenyl, and C 2 -C 16 alkynyl;
  • J is selected from CH and N;
  • X is S, O, or NH when J is CH; and X is S when J is N;
  • R 4 is selected from aryl or aryl substituted with alkyl, such as C 6 -C 30 aryl optionally substituted with one or more C 1 -C 16 alkyl groups, C 6 -C 20 aryl optionally substituted with one or more C 1 -C 16 alkyl groups, and C 6 -C 10 aryl groups optionally substituted with one or more C 1 -C 16 alkyl groups, and where DONOR is as defined below.
  • n is 0. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5;
  • the invention embraces compounds of Formula 1, Formula 2, Formula 3, Formula 4, or Formula 5:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F (Formula 1-F, Formula 2-F, Formula 3-F, Formula 4-F, or Formula 5-F);
  • n is an integer from 0 to 5 inclusive
  • R 2 is selected from H, C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, C 2 -C 16 alkenyl, and C 2 -C 16 alkynyl;
  • J is selected from CH and N;
  • X is S, O, or NH when J is CH; and X is S when J is N;
  • R 4 is selected from aryl or aryl substituted with alkyl, such as C 6 -C 30 aryl optionally substituted with one or more C 1 -C 16 alkyl groups, C 6 -C 20 aryl optionally substituted with one or more C 1 -C 16 alkyl groups, and C 6 -C 10 aryl groups optionally substituted with one or more C 1 -C 16 alkyl groups, and
  • DONOR is as defined below.
  • n is 0. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5. In any of the foregoing embodiments, W can be F.
  • the invention embraces compounds of Formula 6-7-8:
  • P 2 is selected from:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F;
  • n is an integer from 0 to 5 inclusive
  • R 2 is selected from H, C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, C 2 -C 16 alkenyl, and C 2 -C 16 alkynyl;
  • J is selected from CH and N;
  • X is S, O, or NH when J is CH; and X is S when J is N;
  • R 6 is selected from aryl, perfluoroaryl, or aryl substituted with alkyl, such as C 6 -C 30 aryl optionally perfluorinated or optionally substituted with one or more C 1 -C 16 alkyl groups, C 6 -C 20 aryl optionally perfluorinated or optionally substituted with one or more C 1 -C 16 alkyl groups, and C 6 -C 10 aryl groups optionally perfluorinated or optionally substituted with one or more C 1 -C 16 alkyl groups; and
  • DONOR is as defined below.
  • n is 0. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5. In any of the foregoing embodiments, W can be F.
  • the invention embraces compounds of Formula 6, Formula 7, or Formula 8:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F (Formula 6-F, Formula 7-F, or Formula 8-F);
  • n is an integer from 0 to 5 inclusive
  • R 2 is selected from H, C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, C 2 -C 16 alkenyl, and C 2 -C 16 alkynyl;
  • J is selected from CH and N;
  • X is S, O, or NH when J is CH; and X is S when J is N;
  • R 6 is selected from aryl, perfluoroaryl, or aryl substituted with alkyl, such as C 6 -C 30 aryl optionally perfluorinated or optionally substituted with one or more C 1 -C 16 alkyl groups, C 6 -C 20 aryl optionally perfluorinated or optionally substituted with one or more C 1 -C 16 alkyl groups, and C 6 -C 10 aryl groups optionally perfluorinated or optionally substituted with one or more C 1 -C 16 alkyl groups; and
  • DONOR is as defined below.
  • n is 0. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5. In any of the foregoing embodiments, W can be F.
  • the invention embraces compounds of Formula 9-10:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F;
  • n is an integer from 1 to 5 inclusive
  • m is an integer from 0 to 5 inclusive
  • DONOR is as defined below.
  • n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5. In another embodiment, m is 0. In another embodiment, m is 1. In another embodiment, m is 2. In another embodiment, m is 3. In another embodiment, m is 4. In another embodiment, m is 5. In any of the foregoing embodiments, W can be F.
  • the invention embraces compounds of Formula 9 or Formula 10:
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl;
  • W is selected from F, Cl, Br, I, —CN, —CF 3 , —CHF 2 , or —CH 2 F; in a further embodiment, W is F;
  • n is an integer from 1 to 5 inclusive, and m is an integer from 0 to 5 inclusive. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5. In another embodiment, m is 0. In another embodiment, m is 1. In another embodiment, m is 2. In another embodiment, m is 3. In another embodiment, m is 4. In another embodiment, m is 5; and
  • DONOR is as defined below.
  • each DONOR moiety is independently selected from the following group:
  • A is N or P
  • R 11 is selected from C 1 -C 16 alkyl
  • R 12 is selected from C 1 -C 16 alkyl, C 6 -C 20 unsubstituted aryl, or C 6 -C 20 aryl substituted with one or more groups selected from —F, C 1 -C 20 alkyl, C 1 -C 20 fluoroalkyl, —O—C 1 -C 20 alkyl, or —C 1 -C 20 fluoroalkyl;
  • R 13 is selected from C 1 -C 16 alkyl or C 6 -C 20 aryl
  • R 14 is selected from C 1 -C 16 alkyl, —O—C 1 -C 16 alkyl, —C( ⁇ O)—O—C 1 -C 16 alkyl, or —O—C( ⁇ O)—C 1 -C 16 alkyl;
  • R 15 is selected from C 1 -C 16 alkyl, C 6 -C 20 unsubstituted aryl, or C 6 -C 20 aryl substituted with one or more groups selected from —F, C 1 -C 20 alkyl, C 1 -C 20 fluoroalkyl, —O—C 1 -C 20 alkyl, or —C 1 -C 20 fluoroalkyl; and
  • R 16 is selected from C 1 -C 16 alkyl, C 6 -C 20 unsubstituted aryl, or C 6 -C 20 aryl substituted with one or more groups selected from —F, C 1 -C 20 alkyl, C 1 -C 20 fluoroalkyl, —O—C 1 -C 20 alkyl, or —C 1 -C 20 fluoroalkyl.
  • DONOR structures are depicted as divalent; when a DONOR subunit is monovalent (as, for example, in Formula 9-10, Formula 9, and Formula 10 above), one valence is attached to the structure as depicted in the Formula, and one valence is terminated with H or C 1 -C 20 alkyl, such as hexyl or 2-ethylhexyl.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • each DONOR moiety is the same moiety.
  • W can be F.
  • the invention embraces electronic and optoelectronic devices comprising a non-polymeric compound, said compound incorporating one or more groups of Formula A:
  • non-polymeric compound is an electron acceptor or is an electron donor in an active layer of the electronic or optoelectronic device
  • M is selected from sulfur (S), oxygen (O), or N—R 1 , where R 1 is H, C 1 -C 30 alkyl or C 6 -C 30 aryl, and either X 1 is CH and Y 1 is —C(W)—, or X 1 is —C(W)— and Y 1 is CH.
  • M, X 1 , and Y 1 for each moiety is chosen independently of the other moiety or moieties.
  • M is the same for each moiety
  • X 1 is the same for each moiety
  • Y 1 is the same for each moiety.
  • W can be F.
  • the invention embraces electronic and optoelectronic devices comprising a non-polymeric compound, said non-polymeric compound comprising a benzo[c][1,2,5]thiadiazole with an electron-withdrawing substituent W in the 5-position (5BTH), a benzo[c][1,2,5]oxadiazole with an electron-withdrawing substituent W in the 5-position (5BO), a 2H-benzo[d][1,2,3]triazole with an electron-withdrawing substituent W in the 5-position (5BTR), a 5-fluorobenzo[c][1,2,5]thiadiazole (FBTH), a 5-fluorobenzo[c][1,2,5]oxadiazole (FBO), or a 5-fluoro-2H-benzo[d][1,2,3]triazole (FBTR) moiety, wherein said non-polymeric compound is an electron acceptor or is an electron donor in an active layer of the electronic or optoelectronic device.
  • FBTR
  • the invention embraces electronic and optoelectronic devices utilizing the compounds described above.
  • the invention embraces optoelectronic devices, such as organic solar cells, with the general device architecture using the compounds described above as a light harvesting electron donor, comprising:
  • an optional layer or layers adjacent to the first electrode such as an electron-blocking, exciton-blocking, or hole-transporting layer;
  • a layer comprising a mixture of an electron acceptor, such as an organic electron acceptor or an inorganic electron acceptor, and an organic non-polymeric electron donor, said donor comprising one or more compounds selected from Formula I, Formula Ia, Formula Ib, Formula Ic, Formula II, Formula IIa, Formula IIb, Formula IIc, Formula III, Formula IIIa, Formula IIIb, Formula IIIc, Formula IIId, Formula IV-V, Formula IV, Formula IVa, Formula IVb, Formula V, Formula Va, Formula Vb, Formula VI-VII, Formula VI, Formula VIa, Formula VIb, Formula VII, Formula VIIa, Formula VIIb, Formula 1-2-3-4-5, Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6-7-8, Formula 6, Formula 7, Formula 8, Formula 9-10, Formula 9, or Formula 10;
  • an electron acceptor such as an organic electron acceptor or an inorganic electron acceptor
  • an optional layer or layers such as hole-blocking, exciton-blocking, or electron-transporting layers
  • the invention embraces optoelectronic devices, such as organic solar cells, with the general device architecture using the compounds described above as a light harvesting electron acceptor, comprising:
  • an optional layer or layers adjacent to the first electrode such as an electron-blocking, exciton-blocking, or hole-transporting layer;
  • a layer comprising a mixture of an electron donor, such as an organic electron donor or an inorganic electron donor, and an organic non-polymeric electron acceptor material selected from Formula I, Formula Ia, Formula Ib, Formula Ic, Formula II, Formula IIa, Formula IIb, Formula IIc, Formula III, Formula IIIa, Formula IIIb, Formula IIIc, Formula IIId, Formula IV-V, Formula IV, Formula IVa, Formula IVb, Formula V, Formula Va, Formula Vb, Formula VI-VII, Formula VI, Formula VIa, Formula VIb, Formula VII, Formula VIIa, Formula VIIb, Formula 1-2-3-4-5, Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6-7-8, Formula 6, Formula 7, Formula 8, Formula 9-10, Formula 9, or Formula 10;
  • an electron donor such as an organic electron donor or an inorganic electron donor
  • an organic non-polymeric electron acceptor material selected from Formula I, Formula Ia, Formula Ib, Formula Ic, Formula II, Formula IIa, Formula IIb, Formula IIc, Formula III, Formula IIIa, Formula IIIb
  • an optional layer or layers such as hole-blocking, exciton-blocking, or electron-transporting layers
  • the invention embraces devices such as organic field-effect transistors with the general device architecture using the compounds described above as a hole transporting medium, comprising:
  • this dielectric substrate is Si/SiO 2 ; 2) an optional layer or layers adjacent the dielectric substrate, used to modify the surface energy of the dielectric and/or to facilitate deposition of the active layer;
  • an active layer comprising an organic non-polymeric hole transporting material selected from Formula I, Formula Ia, Formula Ib, Formula Ic, Formula II, Formula IIa, Formula IIb, Formula IIc, Formula III, Formula IIIa, Formula IIIb, Formula IIIc, Formula IIId, Formula IV-V, Formula IV, Formula IVa, Formula IVb, Formula V, Formula Va, Formula Vb, Formula VI-VII, Formula VI, Formula VIa, Formula VIb, Formula VII, Formula VIIa, Formula VIIb, Formula 1-2-3-4-5, Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6-7-8, Formula 6, Formula 7, Formula 8, Formula 9-10, Formula 9, or Formula 10; and
  • the invention embraces devices, such as organic field-effect transistors with the general device architecture using the compounds described above as an electron transporting medium, comprising:
  • this dielectric substrate is Si/SiO 2 ;
  • an active layer comprising an organic non-polymeric electron transporting material selected from Formula I, Formula Ia, Formula Ib, Formula Ic, Formula II, Formula IIa, Formula IIb, Formula IIc, Formula III, Formula IIIa, Formula IIIb, Formula IIIc, Formula IIId, Formula IV-V, Formula IV, Formula IVa, Formula IVb, Formula V, Formula Va, Formula Vb, Formula VI-VII, Formula VI, Formula VIa, Formula VIb, Formula VII, Formula VIIa, Formula VIIb, Formula 1-2-3-4-5, Formula 1, Formula 2, Formula 3, Formula 4, Formula 5, Formula 6-7-8, Formula 6, Formula 7, Formula 8, Formula 9-10, Formula 9, or Formula 10; and
  • FIG. 1 shows the absorption spectra of ( FIG. 1A ) p-DTS(FBTTh 2 ) 2 solution in chloroform, thin film and annealed film; ( FIG. 1B ) p-DTS(FBTTh 2 ) 2 with various equivalents of trifluoroacetic acid in chloroform; and ( FIG. 1C ) d-DTS(PTTh 2 ) 2 with various equivalents of trifluoroacetic acid in chloroform.
  • FIG. 2 shows current voltage characteristics of solar cells with an active layer comprised of p-DTS(FBTTh 2 ) 2 and PC 71 BM as cast, annealed and with 0.4% (v/v) diiodooctane solvent additive.
  • FIG. 3 shows the external quantum efficiency of the solar cells of FIG. 2 .
  • Alkyl is intended to embrace a saturated linear, branched, cyclic, or a combination of linear and/or branched and/or cyclic hydrocarbon chain(s) and/or ring(s) having the number of carbon atoms specified, or if no number is specified, having 1 to 16 carbon atoms.
  • Alkenyl is intended to embrace a linear, branched, cyclic, or a combination of linear and/or branched and/or cyclic hydrocarbon chain(s) and/or ring(s) having at least one carbon-carbon double bond, and having the number of carbon atoms specified, or if no number is specified, having 2 to 16 carbon atoms.
  • Alkynyl is intended to embrace a linear, branched, cyclic, or a combination of linear and/or branched and/or cyclic hydrocarbon chain(s) and/or ring(s) having at least one carbon-carbon triple bond, and having the number of carbon atoms specified, or if no number is specified, having 2 to 19 carbon atoms, preferably 2 to 16 carbon atoms.
  • Fluoroalkyl indicates an alkyl group where at least one hydrogen of the alkyl group has been replaced with a fluorine substituent.
  • Aryl is defined as an optionally substituted aromatic ring system.
  • Aryl groups include monocyclic aromatic rings, polyaromatic ring systems, and polycyclic aromatic ring systems containing the number of carbon atoms specified, or if no number is specified, containing six to thirty carbon atoms. In other embodiments, aryl groups may contain six to twenty carbon atoms, six to twelve carbon atoms, or six to ten carbon atoms. In other embodiments, aryl groups can be unsubstituted.
  • Heteroaryl is defined as an optionally substituted aromatic ring system. Heteroaryl groups contain the number of carbon atoms specified, and one or more heteroatoms (such as one to six heteroatoms, or one to three heteroatoms), where heteroatoms include, but are not limited to, oxygen, nitrogen, sulfur, and phosphorus. In other embodiments, heteroaryl groups may contain six to twenty carbon atoms and one to four heteroatoms, six to twelve carbon atoms and one to three heteroatoms, six to ten carbon atoms and one to three heteroatoms, or three to six carbon atoms and one to three heteroatoms. In other embodiments, heteroaryl groups can be unsubstituted.
  • Polymer or “polymeric molecule” is defined herein as a structure containing at least eight repeating units.
  • a “non-polymeric” molecule is a molecule containing seven or fewer repeating units.
  • monomers, dimers, trimers, tetramers, pentamers, hexamers, and heptamers are non-polymeric molecules for the purposes of this disclosure.
  • Interruption of a repeating unit “resets” the count of subunits for the purposes of this disclosure; thus, for example, for a molecule such as Formula 6:
  • the molecule when n is 5, the molecule is considered to have two separate five-subunit pieces, that is, it is comprised of two pentathiophene units, and is not considered a decamer or 10-subunit polymer of thiophene.
  • Non-polymeric molecules typically have a discrete molecular weight, while polymeric molecules typically have a distribution of molecular weights due to varying numbers of monomers that are incorporated into the growing chain during polymerization.
  • a preparation of a non-polymeric molecule will be characterized by a single molecular weight (where the molecular weight is averaged only over isotopic variation due to differing isotopes such as hydrogen, deuterium, carbon-12, carbon-13, etc.) of about 90%, preferably 95%, more preferably 98%, still more preferably 99%, of the molecular species.
  • preparations of a polymeric molecule will typically have a distribution of molecular weights due to varying numbers of monomers in the final polymer, where the molecular weight is an average over each individual polymeric species present in a given preparation (measured in either number-average molecular weight or weight-average molecular weight).
  • the current invention describes chromophores incorporating benzo[c][1,2,5]thiadiazoles with an electron-withdrawing substituent W in the 5-position (5BTH), benzo[c][1,2,5]oxadiazoles with an electron-withdrawing substituent W in the 5-position (5BO), 2H-benzo[d][1,2,3]triazoles (5BTR) with an electron-withdrawing substituent W in the 5-position (5BTR),5-fluorobenzo[c][1,2,5]thiadiazoles (FBTH), 5-fluorobenzo[c][1,2,5]oxadiazoles (FBO), or 5-fluoro-2H-benzo[d][1,2,3]triazoles (FBTR).
  • a subunit of this type permits the manipulation of electronic levels without adding a reactive site, such as the pyridine nitrogen on pyridal[2,1,3]thiadiazole (PT)-type compounds, which is susceptible to protonation when deposited from acidic solution, or when used with materials having labile protons such as PEDOT:PSS.
  • a reactive site such as the pyridine nitrogen on pyridal[2,1,3]thiadiazole (PT)-type compounds, which is susceptible to protonation when deposited from acidic solution, or when used with materials having labile protons such as PEDOT:PSS.
  • the fluorine atom also imparts asymmetric reactivity to the corresponding dibromide compound (such as FBTHBr 2 ), which allows for facile synthetic access to the desired structure.
  • FBTHBr 2 dibromide compound
  • Optical properties were investigated using UV-visible absorption spectroscopy.
  • p-DTS(FBTTh 2 ) 2 exhibits broad low energy transitions with favorable overlap with the solar spectrum with ⁇ max values of 590 nm (solution) and 678 nm (solid state), and ⁇ onset values of 670 nm (solution) and 800 nm (solid state), corresponding to optical band gaps of 1.85 and 1.55 eV, respectively; see FIG. 1A .
  • Thin film absorption exhibits a red-shifted spectrum as well as the development of vibronic structure in optical profiles, typical of ordered thin films.
  • HOMO highest occupied molecular orbital
  • LUMO lowest unoccupied molecular orbital
  • FIG. 1B shows that the absorption of p-DTS(FBTTh 2 ) 2 remains effectively unchanged with up to ten equivalents of acid.
  • the pyridal analog shows significant changes in its absorption spectrum as soon as acid is introduced, as shown in FIG. 1C .
  • the effect manifests as a new low-energy transition, suggesting that the chromophore backbone, where low-energy transition dipoles reside, is affected by the acid.
  • 5BTH moieties can be attached to a benzodithiophene core via the synthesis outlined in Scheme 2. Similar chemistry—that is, coupling of trimethylstannate derivatives of one moiety to bromo derivatives of another moiety—can be employed to assemble any of the various molecules described herein.
  • the current invention provides several advantages for preparation of optoelectronic devices.
  • the organic materials described are non-polymeric allowing for synthesis and purification producers to be more repeatable than organic polymers. Unlike polymers, the organic materials described are discrete mono-disperse small molecules which allows for their exact structure to be known and reproduced. Synthesis of organic small molecule chromophores containing the 5BTH, 5BO, 5BTR, FBTH, FBO, or FBTR organic structures is straightforward, and methods used for the pyridalthiadiazole (PT, [1,2,5]thiadiazolo[3,4-c]pyridine) organic structure (see M. Leclerc et al.
  • the compounds are readily handled in solution, as the organic small molecule chromophores described retain good solubility in many common organic solvents, and are soluble in aqueous solvents, including acidic aqueous solvents. This allows solution processing during the preparation of the optoelectronic devices.
  • vapor deposition can also be used for the molecules, or mixtures of said molecules with other components, which are suitable for use in such a method (e.g., vacuum deposition, physical vapor deposition, chemical vapor deposition).
  • the optoelectronic device of the invention comprises the following layers:
  • an optional layer or layers adjacent to the first electrode such as an electron-blocking, exciton-blocking, or hole-transporting layer;
  • an optional layer or layers such as hole-blocking, exciton-blocking, or electron-transporting layers;
  • the first electrode can be transparent, allowing light to enter the device, but in some embodiments, the second electrode can be transparent. In some embodiments, both electrodes are transparent.
  • the first electrode (layer “a”) is deposited onto a substrate, and the device is fabricated by subsequent deposition of layers “b” (if present), “c”, “d” (if present), and “e”.
  • the second electrode “e” can be deposited onto a substrate, with subsequent deposition of layers “d” (if present), “c”, “b” (if present), and “a”.
  • the optoelectronic device of the invention comprises the following layers:
  • ITO indium tin oxide
  • PEDOT:PSS poly(3,4-ethylene dioxythiophene:poly(styrenesulfonate)
  • PDOT:PSS poly(styrenesulfonate)
  • MoO3 metal oxide
  • the first electrode (layer “a”) is deposited onto the substrate, and the device is fabricated by subsequent deposition of layers “b”, “c”, and “e”.
  • the second electrode “e” can be deposited onto a substrate, with subsequent deposition of layers “c”, “b”, and “a”.
  • the 5BTH, 5BO, 5BTR, FBTH, FBO, or FBTR electron donors or electron acceptors can be used in tandem solar cells, such as those disclosed in US 2009/0126779. Tandem solar cells are arranged so that light which is not absorbed by a first solar cell passes to a second solar cell, where the second solar cell typically has a smaller bandgap than the first solar cell in order to absorb electromagnetic radiation that cannot be usefully absorbed by the first solar cell.
  • the device can comprise a first cell and a second cell arranged in tandem.
  • the first cell is configured to receive incident electromagnetic radiation and includes a first charge separating layer having a first semiconducting polymer adapted to create electric charge carriers generated by electromagnetic radiation.
  • the second cell is configured to receive electromagnetic radiation passing out of the first cell in a light propagation path.
  • the second cell includes a second charge separating layer having a second semiconducting polymer adapted to create electric charge carriers generated by electromagnetic radiation.
  • a layer separates the two cells, such as a titanium oxide layer which is interposed between the first and second cells.
  • the titanium oxide layer can be substantially amorphous and can have a general formula of TiO x where x is a number of about 1 to about 1.96; that is, the titanium oxide layer can be sub-stoichiometric titanium dioxide, or amorphous sub-stoichiometric titanium dioxide.
  • Passivating layers such as those disclosed in US 2007/0221926 and US 2007/0169816, can be incorporated into devices using the 5BTH, 5BO, 5BTR, FBTH, FBO, or FBTR electron donors or electron acceptors.
  • Optical spacer layers such as those disclosed in US 2006/0292736, can also be employed in devices using the 5BTH, 5BO, 5BTR, FBTH, FBO, or FBTR electron donors or electron acceptors.
  • a transparent first electrode such as ITO-coated glass
  • the donor:acceptor mixture where light passes though a transparent first electrode (such as ITO-coated glass), it is absorbed by the donor:acceptor mixture, which results in the separation of electrical charges and migration of the charges to the electrodes, yielding a usable electrical potential.
  • the first electrode can be made of materials such as indium-tin oxide, indium-magnesium oxide, cadmium tin-oxide, tin oxide, aluminum- or indium-doped zinc oxide, gold, silver, nickel, palladium and platinum.
  • the first electrode has a high work function (4.3 eV or higher).
  • the first electrode is transparent.
  • the optional layer adjacent to the first electrode is preferably polystyrenesulfonic acid-doped polyethylenedioxythiophene (PEDOT:PSS).
  • PEDOT polystyrenesulfonic acid-doped polyethylenedioxythiophene
  • Other hole transporting materials such as polyaniline (with suitable dopants), or N,N′-diphenyl-N,N′-bis(3-methylphenyl)[1,1′-biphenyl]-4,4′-diamine (TPD), nickel oxide, can be used.
  • Electron-blocking, exciton-blocking, or hole-transporting metal oxides such as MoO 3 , MoO 3-x , V 2 O 5-x , NiO, Ta 2 O 5 , Ag 2 O, CuO, Cu 2 O, CrO 3-x , and WO 3 , where x is between 0.01 and 0.99, more preferably between 0.1 and 0.9, can be used as materials between the hole-transporting electrode and the active layer.
  • Other suitable materials are described in Greiner, Mark T. et al., “Universal energy-level alignment of molecules on metal oxides,” Nature Materials, DOI: 10.1038/NMAT3159 (Nov. 6, 2011).
  • a conductive, transparent substrate is prepared from commercially available indium tin oxide-coated glass and polystyrenesulfonic acid doped polyethylenedioxythiophene using standard procedures.
  • a solution containing a mixture of the donor and acceptor materials is prepared so that the ratio of donor to acceptor is between 1:99 and 99:1 parts by mass; more preferably between 3:7 and 7:3 parts by mass.
  • the overall concentration of the solution may range between 0.1 mg/mL and 100 mg/mL, but is preferably in the range of 10 mg/mL and 30 mg/mL.
  • 5BTH, 5BO, 5BTR, FBTH, FBO, or FBTR non-polymeric molecules are used that have a solubility of at least about 0.1 mg/mL in an organic solvent, 1 mg/mL in an organic solvent, 5 mg/mL, 10 mg/mL in an organic solvent, 30 mg/mL in an organic solvent, or 100 mg/mL in an organic solvent.
  • the organic solvent can be selected from chloroform, toluene, chlorobenzene, dichloromethane, tetrahydrofuran, or carbon disulfide.
  • the electron acceptor is preferably [6,6]-phenyl C61-butyric acid methyl ester (PCBM), but may be a different fullerene (including, but not limited to, C71-PCBM), a tetracyanoquinodimethane, a vinazene, a perylene tetracarboxylic acid-dianhydride, a perylene tetracarboxylic acid-diimide, an oxadiazole, carbon nanotubes, or any other organic electron acceptor, such as those compounds disclosed in U.S. 2008/0315187.
  • PCBM [6,6]-phenyl C61-butyric acid methyl ester
  • the electron acceptor is an inorganic acceptor selected from TiO 2 (titanium dioxide), TiO x (titanium suboxide, where x ⁇ 2) and ZnO (zinc oxide).
  • the titanium dioxide can be anatase, rutile, or amorphous.
  • a titanium dioxide layer can be prepared by depositing a sol-gel precursor solution, for example by spincasting or doctorblading, and sintering at a temperature between about 300° C. and 500° C.
  • component (c) of the optoelectronic device described above can be comprised of a layer of electron-donating chromophores of the general Formula I-VII and an inorganic electron-acceptor layer.
  • the inorganic material can be dispersed in the electron-donating chromophores to create a single layer.
  • Preparation of TiO 2 for use in solar cells is described in Brian O'Regan & Michael Grätzel, Nature 353:737 (1991) and Serap Günes et al., 2008 Nanotechnology 19 424009.
  • x is preferably 1 ⁇ x ⁇ 1.98, 1.1 ⁇ x ⁇ 1.9, 1.2 ⁇ x ⁇ 1.8, or 1.3 ⁇ x ⁇ 1.8.
  • X in the formula TiO x can be ⁇ 2, ⁇ 1.98, ⁇ 1.9, ⁇ 1.8, ⁇ 1.7, or ⁇ 1.6.
  • Useful solvents include chloroform, toluene, chlorobenzene, dichloromethane, tetrahydrofuran, and carbon disulfide.
  • the solvent used may be any solvent which dissolves or partially dissolve both donor and acceptor materials and has a non-zero vapor pressure.
  • the solution of donor and acceptor is deposited by spin casting, doctor-blading, ink-jet printing, roll-to-roll coating, slot-dye coating, gravure coating, or any process which yields a continuous film of the donor-acceptor mixture such that the thickness of the film is within the range of 10 to 1000 nm, more preferably between 50 and 150 nm.
  • the layer of the donor and acceptor is cast from a solution comprising a solvent and the electron donor and the electron acceptor.
  • the solvent can comprise chloroform, thiophene, trichloroethylene, chlorobenzene, carbon disulfide, a mixture of any of the foregoing solvents or any solvent or solvent mixture that dissolves both the donor and acceptor organic small molecule.
  • the solvent can also include processing additives, such as those disclosed in US Patent Application Publication Nos. 2009/0032808, 2008/0315187, or 2009/0108255. For example, 1,8-diiodooctane (DIO) can be added to the solvent/donor/acceptor mixture in an amount of 0.1-10% by volume.
  • DIO 1,8-diiodooctane
  • the additive such as 2% DIO, can be added to any organic solvent used to cast the layer of donor/acceptor, such as chloroform.
  • the solvent can also include doping agents such as molybdenum trioxide (MoO 3 ).
  • MoO 3 can be added to the solvent/donor/acceptor mixture in an amount of 0.1-10% by volume.
  • An additional layer or layers of material may optionally be deposited on top of the donor-acceptor film in order to block holes or excitons, act as an optical buffer, or otherwise benefit the electrical characteristics of the device.
  • 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline can act as a hole-blocking or exciton-blocking material
  • 4,4′,4′′-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine and polyethylene dioxythiophene can act as exciton-blocking materials.
  • Other materials that can be used between the second electrode and the active layer are titanium suboxide, ZnO, Cs 2 CO 3 , and ZrO 3 . Additional materials suitable for use are described in Greiner, Mark T. et al., “Universal energy-level alignment of molecules on metal oxides,” Nature Materials, DOI: 10.1038/NMAT3159 (Nov. 6, 2011).
  • an electrode such as a metal electrode
  • a metal electrode is deposited on top of the structure by thermal evaporation, sputtering, printing, lamination or some other process.
  • Conducting metal oxides such as indium tin oxide, zinc oxide, or cadmium oxide, can also be used as electrodes, as well as conducting organic materials, such as electrodes comprising graphene.
  • the metal is preferably aluminum, silver or magnesium, but may be any metal. Nanowires such as silver nanowires can also be used. If a transparent electrode is desired, very thin metallic sheets of metals can also be used.
  • the device is annealed before and/or after evaporation of the metal electrode.
  • the electron and hole mobilities are both on the order of 10 ⁇ 4 cm 2 /Vs or higher. More preferably, the electron mobilities are on the order of 10 ⁇ 3 cm 2 /Vs or higher. In some embodiments, the electron mobilities are on the order of 10 ⁇ 4 cm 2 /Vs or higher, and the hole mobilities are between 10 ⁇ 8 cm 2 /Vs and 10 4 cm 2 /Vs or higher. In other embodiments, the electron mobilities are on the order of 10 ⁇ 3 cm 2 /Vs or higher, and the hole mobilities are between 10 ⁇ 8 cm 2 /Vs and 10 ⁇ 4 cm 2 /Vs or higher.
  • Optoelectronic devices of the present invention have excellent photovoltaic properties.
  • the power conversion efficiency (PCE) is at least 0.5%, at least 1.0%, at least 2.0%, or at least 3.0%.
  • the short circuit current density is greater than 3.0 mA/cm 2 , and preferably greater than 8 mA/cm 2 .
  • the open circuit voltage is between 0.3 and 1.0 V or higher.
  • the device exhibits an external quantum efficiency of approximately 35% or greater between 300 and 800 nm.
  • the morphological properties of the donor:acceptor films can be measured using atomic force microscopy or other surface-sensitive techniques.
  • the films will have a root-mean-squared surface roughness of less than 1.0 nm, more preferably less than 0.5 nm
  • inverted device architecture where the substrate act as a cathode, while the top electrode acts as the anode.
  • using the substrate to collect electrons can allow a stable, high work function metal such as gold or nickel to be used as the top electrode. This can be achieved by modifying the work function of the substrate or using an n-type substrate.
  • Inverted device architecture is described in, for example, Hau et al. (2010) “A Review on the Development of the Inverted Polymer Solar Cell Architecture,” Polymer Reviews 50(4):474-510, in Jen et al., US 2009/0188558, and in Nguyen et al. US 2010/0326525 (see FIG. 19B ).
  • photo-generated holes travel to an ITO substrate while photo-generated electrons travel to a top electrode consisting of a relatively low work-function metal such as Al.
  • a relatively low work-function metal such as Al
  • the charge carriers flow in the opposite direction, where electrons travel to the ITO substrate while holes travel to the top electrode and are collected by a relatively high work function metal such as Au.
  • This configuration has the advantage that a relatively stable metal is used as the top electrode, which can increase the lifetime of the device.
  • the first electrode can comprise Au or another material having a work function higher than the work function of the second electrode
  • the second electrode can comprise an ITO substrate modified using a self-assembled monolayer of 3-aminopropyltrimethoxysiloxane or another material having a work function lower than the work function of the first electrode.
  • the compounds of the invention can also be used to make inverted tandem solar cells, such as a cell having the layers of a transparent substrate, a transparent conductor, an electron injection/transport layer, an active layer with a wider band gap organic semiconductor, a hole injection/transport layer, an electron injection/transport layer (which facilitates recombination between the front and back cells), an active layer with a smaller band gap organic semiconductor, a hole injection/transport layer, and a top metal electrode.
  • a cell using this architecture is described in Dou et al., Nature Photonics 6:180-185 (2012).
  • DTS—Br 2 Compound 5,5′-dibromo-3,3′-di-2-ethylhexylsilylene-2,2′-bithiophene (DTS—Br 2 ) was purchased from Luminescence Technology Corp. (Lumtec) and used as received.
  • Stannanes reported that were not purchased were prepared according to literature procedure (Coffin, R.; Peet, J.; Rogers, J.; Bazan, G. C. Nat. Chem. 2009; 1(8):657-661).
  • DTS—Br 2 Compound 5,5′-dibromo-3,3′-di-2-ethylhexylsilylene-2,2′-bithiophene (DTS—Br 2 ) was purchased from Luminescence Technology Corp. (Lumtec) and used as received.
  • Stannanes reported that were not purchased were prepared according to literature procedure (Coffin, R.; Peet, J.; Rogers, J.; Bazan, G. C. Nat. Chem. 2009; 1(8):657-661).
  • UV-visible spectroscopy were recorded using either a Beckman Coulter DU 800 series or Perkin Elmer Lambda 750 spectrophotometer at room temperature unless otherwise noted. All solution UV-vis experiments were run in CHCl 3 . Films were prepared by spin-coating CHCl 3 or chlorobenzene solutions onto glass substrates Films were annealed directly on a hot plate for 2 minutes.
  • DSC Differential scanning calorimetry
  • Devices were prepared on cleaned, UV/ozone treated Corning 1737 glass patterened with 140 nm ITO. Active layers were spun cast to give 100 nm thicknesses (as determined using an Ambios XP-100 stylus profilometer) from solutions of p-DTS(FBTTh 2 ) 2 and PC 71 BM at a weight ratio of 60:40 in chlorobenzene with or without 0.2% diiodo octane by volume, at an overall concentration of 35 mg mL ⁇ 1 . Solutions were heated for several hours and residual solids filtered prior to casting at 90° C. Films were allowed to dry for 30 mins then heated to 70° C. for 10 mins under inert atmosphere to drive off residual solvent.
  • Cathodes were deposited by sequential thermal evaporation of 5 nm Ca followed by 100 nm Al. Device characteristics were measured under illumination by a simulated 100 mWcm ⁇ 2 AM1.5G light source using a 300 W Xe arc lamp with an AM 1.5 global filter. Solar-simulator irradience was calibrated using a standard silicon photovoltaic with a protective KG1 filter calibrated by the National Renewable Energy Laboratory. External quantum efficienceis were determined using a 75 W Xe source, monochromator, optical chopper, lock-in amplifier, and a National Institute of Standards and Technology-calibrated silicon photodiode was used for power-density calibration. Mismatch factors of the integrated quantum efficiency for devices was calculated to be less than 6%.

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