US20130062598A1 - Compounds Having Semiconducting Properties and Related Compositions and Devices - Google Patents

Compounds Having Semiconducting Properties and Related Compositions and Devices Download PDF

Info

Publication number
US20130062598A1
US20130062598A1 US13/608,976 US201213608976A US2013062598A1 US 20130062598 A1 US20130062598 A1 US 20130062598A1 US 201213608976 A US201213608976 A US 201213608976A US 2013062598 A1 US2013062598 A1 US 2013062598A1
Authority
US
United States
Prior art keywords
compound
linear
independently
formula
mmol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US13/608,976
Other languages
English (en)
Inventor
Hakan Usta
Damien Boudinet
Jordan Quinn
Antonio Facchetti
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Polyera Corp
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to US13/608,976 priority Critical patent/US20130062598A1/en
Publication of US20130062598A1 publication Critical patent/US20130062598A1/en
Assigned to POLYERA CORPORATION reassignment POLYERA CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BOUDINET, Damien, FACCHETTI, ANTONIO, USTA, HAKAN, QUINN, JORDAN
Priority to US15/137,939 priority patent/US9911927B2/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic 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
    • C07D495/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/464—Lateral top-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
    • H10K10/471—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only organic materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
    • H10K10/472—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only inorganic materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • H10K10/486—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising two or more active layers, e.g. forming pn heterojunctions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/30—Organic light-emitting transistors

Definitions

  • Organic optoelectronic devices such as organic thin film transistors (OTFTs), organic light emitting diodes (OLEDs), organic light emitting transistors (OLETs), printable circuits, organic photovoltaic devices, capacitors and sensors are fabricated using small molecule or polymeric semiconductors as their active components.
  • OFTs organic thin film transistors
  • OLEDs organic light emitting diodes
  • OLETs organic light emitting transistors
  • printable circuits organic photovoltaic devices
  • capacitors and sensors are fabricated using small molecule or polymeric semiconductors as their active components.
  • ⁇ charge carrier mobility
  • the present teachings relate to new semiconducting compounds that can exhibit properties such as good charge transport characteristics under ambient conditions, chemical stability, low-temperature processability, large solubility in common solvents, and processing versatility.
  • semiconductor devices such as thin film transistors and light emitting transistors that incorporate the present compounds as the semiconductor layer can have high performance under ambient conditions, for example, demonstrating one or more of large electron mobilities, low threshold voltages, and high current on-off ratios.
  • the present teachings also provide methods of preparing semiconductor materials, as well as various compositions, composites, and devices that incorporate the compounds and semiconductor materials disclosed herein.
  • FIG. 1 illustrates four different configurations of thin film transistors: bottom-gate top contact (a), bottom-gate bottom-contact (b), top-gate bottom-contact (c), and top-gate top-contact (d); each of which can be used to incorporate compounds of the present teachings.
  • FIG. 2 shows representative transfer plots of 2,9-1MP-DNTT-based OTFT devices (top-gate bottom-contact) at different channel lengths (L).
  • compositions are described as having, including, or comprising specific components, or where processes are described as having, including, or comprising specific process steps, it is contemplated that compositions of the present teachings also consist essentially of, or consist of, the recited components, and that the processes of the present teachings also consist essentially of, or consist of, the recited process steps.
  • halo or “halogen” refers to fluoro, chloro, bromo, and iodo.
  • alkyl refers to a straight-chain or branched saturated hydrocarbon group.
  • alkyl groups include methyl (Me), ethyl (Et), propyl (e.g., n-propyl and iso-propyl), butyl (e.g., n-butyl, iso-butyl, sec-butyl, tert-butyl), pentyl groups (e.g., n-pentyl, iso-pentyl, neopentyl), hexyl groups, and the like.
  • an alkyl group can have 1 to 40 carbon atoms (i.e., C 1-40 alkyl group), for example, 1-20 carbon atoms (i.e., C 1-20 alkyl group).
  • an alkyl group can have 1 to 6 carbon atoms, and can be referred to as a “lower alkyl group.” Examples of lower alkyl groups include methyl, ethyl, propyl (e.g., n-propyl and iso-propyl), and butyl groups (e.g., n-butyl, iso-butyl, sec-butyl, tert-butyl).
  • haloalkyl refers to an alkyl group having one or more halogen substituents.
  • a haloalkyl group can have 1 to 40 carbon atoms (i.e., C 1-40 haloalkyl group), for example, 1 to 20 carbon atoms (i.e., C 1-20 haloalkyl group).
  • Examples of haloalkyl groups include CF 3 , C 2 F 5 , CHF 2 , CH 2 F, CCl 3 , CHCl 2 , CH 2 Cl, C 2 Cl 5 , and the like.
  • Perhaloalkyl groups i.e., alkyl groups where all of the hydrogen atoms are replaced with halogen atoms (e.g., CF 3 and C 2 F 5 ), are included within the definition of “haloalkyl.”
  • a C 1-40 haloalkyl group can have the formula —C s H 2s+1 ⁇ t X 0 t , where X 0 , at each occurrence, is F, Cl, Br or I, s is an integer in the range of 1 to 40, and t is an integer in the range of 1 to 81, provided that t is less than or equal to 2s+1.
  • Haloalkyl groups that are not perhaloalkyl groups can be substituted as described herein.
  • alkenyl refers to a straight-chain or branched alkyl group having one or more carbon-carbon double bonds.
  • alkenyl groups include ethenyl, propenyl, butenyl, pentenyl, hexenyl, butadienyl, pentadienyl, hexadienyl groups, and the like.
  • the one or more carbon-carbon double bonds can be internal (such as in 2-butene) or terminal (such as in 1-butene).
  • an alkenyl group can have 2 to 40 carbon atoms (i.e., C 2-40 alkenyl group), for example, 2 to 20 carbon atoms (i.e., C 2-20 alkenyl group).
  • substituents are disclosed in groups or in ranges. It is specifically intended that the description include each and every individual subcombination of the members of such groups and ranges.
  • C 1-6 alkyl is specifically intended to individually disclose C 1 , C 2 , C 3 , C 4 , C 5 , C 6 ,
  • an integer in the range of 0 to 40 is specifically intended to individually disclose 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, and 40, and an integer in the range of 1 to 20 is specifically intended to individually disclose 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20.
  • phrases “optionally substituted with 1-5 substituents” is specifically intended to individually disclose a chemical group that can include 0, 1, 2, 3, 4, 5, 0-5, 0-4, 0-3, 0-2, 0-1, 1-5, 1-4, 1-3, 1-2, 2-5, 2-4, 2-3, 3-5, 3-4, and 4-5 substituents.
  • asymmetric atom also referred as a chiral center
  • some of the compounds can contain two or more asymmetric atoms or centers, which can thus give rise to optical isomers (enantiomers) and diastereomers (geometric isomers).
  • the present teachings include such optical isomers and diastereomers, including their respective resolved enantiomerically or diastereomerically pure isomers (e.g., (+) or ( ⁇ ) stereoisomer) and their racemic mixtures, as well as other mixtures of the enantiomers and diastereomers.
  • optical isomers can be obtained in enantiomerically enriched or pure form by standard procedures known to those skilled in the art, which include, for example, chiral separation, diastereomeric salt formation, kinetic resolution, and asymmetric synthesis.
  • the present teachings also encompass cis- and trans-isomers of compounds containing alkenyl moieties (e.g., alkenes, azo, and imines). It also should be understood that the compounds of the present teachings encompass all possible regioisomers in pure form and mixtures thereof.
  • the preparation of the present compounds can include separating such isomers using standard separation procedures known to those skilled in the art, for example, by using one or more of column chromatography, thin-layer chromatography, simulated moving-bed chromatography, and high-performance liquid chromatography.
  • column chromatography thin-layer chromatography
  • simulated moving-bed chromatography simulated moving-bed chromatography
  • high-performance liquid chromatography mixtures of regioisomers can be used similarly to the uses of each individual regioisomer of the present teachings as described herein and/or known by a skilled artisan.
  • a “p-type semiconductor material” or a “p-type semiconductor” refers to a semiconductor material having holes as the majority current carriers.
  • a p-type semiconductor material when deposited on a substrate, it can provide a hole mobility in excess of about 10 ⁇ 5 cm 2 /Vs.
  • a p-type semiconductor in the case of field-effect devices, can also exhibit a current on/off ratio of greater than about 10.
  • an “n-type semiconductor material” or an “n-type semiconductor” refers to a semiconductor material having electrons as the majority current carriers.
  • an n-type semiconductor material when deposited on a substrate, it can provide an electron mobility in excess of about 10 ⁇ 5 cm 2 /Vs.
  • an n-type semiconductor can also exhibit a current on/off ratio of greater than about 10.
  • mobility refers to a measure of the velocity with which charge carriers, for example, holes (or units of positive charge) in the case of a p-type semiconductor material and electrons in the case of an n-type semiconductor material, move through the material under the influence of an electric field. This parameter, which depends on the device architecture, can be measured using a field-effect device or space-charge limited current measurements.
  • the present teachings provide various semiconducting small molecule compounds (small molecule semiconductors) as well as compositions and organic semiconductor materials prepared from such compounds and compositions.
  • the organic semiconductor materials disclosed herein can exhibit useful electrical properties and can be solution-processable, e.g., spin-coatable and printable.
  • the semiconductor materials disclosed herein can be used to fabricate various organic electronic articles, structures and devices, including field-effect transistors, light emitting transistors, unipolar circuitries, complementary circuitries, and photovoltaic devices.
  • the present compounds can be represented by formula II-IV:
  • Z can be H.
  • Z can be CHR 1 R 1 ′ , in which case, R 1 can be the same or different from R 1 ′.
  • R 2 can be different from R 2 ′.
  • R 1 ′ and R 2 ′ can be selected from a linear C 1-6 alkyl group, a linear C 2-6 alkenyl group, and a linear C 1-6 haloalkyl group; whereas R 1 and R 2 can be selected from a linear C 3-40 alkyl group, a linear C 3-40 alkenyl group, and a linear C 3-40 haloalkyl group; preferably selected from a linear C 6-40 alkyl group, a linear C 6-40 alkenyl group, and a linear C 6-40 haloalkyl group; more preferably selected from a linear C 8-40 alkyl group, a linear C 8-40 alkenyl group, and a linear C 8-40 haloalkyl group.
  • R 1 ′ and R 2 ′ can be selected from CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 ; whereas R 1 and R 2 can be selected from a linear C 3-20 alkyl group, a linear C 3-20 alkenyl group, and a linear C 3-20 haloalkyl group.
  • the present compounds can be represented by formula IIa, IIIa, or IVa:
  • R 1 and R 2 independently are selected from C 2 H 5 , n-C 3 H 7 , n-C 4 H 9 , n-C 5 H 11 , n-C 6 H 13 , n-C 7 H 15 , n-C 8 H 17 , n-C 9 H 19 , n-C 10 H 21 , n-C 11 H 23 , and n-C 12 H 25 ; and m 1 and m 2 independently are selected from 0, 1, and 2.
  • the present compounds can be optically pure stereoisomers.
  • certain compounds of formula II-IV can be stereospecific and can be represented by formula IIb, IIIb, IVb, IIc, IIIc, or IVc:
  • R 1 and R 2 independently are selected from C 2 H 5 , n-C 3 H 7 , n-C 4 H 9 , n-C 5 H 11 , n-C 6 H 13 , n-C 7 H 15 , n-C 8 H 17 , n-C 9 H 19 , n-C 10 H 21 , n-C 11 H 23 , and n-C 12 H 25 ; and m 1 and m 2 independently are selected from 0, 1, and 2.
  • the present compounds can be represented by formula V, VI, or VII:
  • R 2 is selected from a linear C 3-40 alkyl group, a linear C 3-40 alkenyl group, and a linear C 3-40 haloalkyl group;
  • R 2 ′ is selected from CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 ;
  • m 1 and m 2 independently are selected from 0, 1, and 2.
  • the present compounds can be optically pure stereoisomers.
  • certain compounds of formula V-VII can be stereospecific and can be represented by formula Va, VIa, oVIIa, Vb, VIb, or VIIb:
  • R 2 is selected from a linear C 3-40 alkyl group, a linear C 3-40 alkenyl group, and a linear C 3-40 haloalkyl group
  • R 2 ′ is selected from CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5
  • m 1 and m 2 independently are selected from 0, 1, and 2.
  • each m can be the same or different.
  • certain embodiments of the present compounds can be represented by formula:
  • R 1 and R 2 independently are selected from a linear C 3-40 alkyl group, a linear C 3-40 alkenyl group, and a linear C 3-40 haloalkyl group.
  • X and Y can be different.
  • certain compounds of formula I can be represented by formula:
  • R 1 and R 2 independently are selected from a linear C 3-40 alkyl group, a linear C 3-40 alkenyl group, and a linear C 3-40 haloalkyl group.
  • R 2 is selected from a linear C 3-40 alkyl group, a linear C 3-40 alkenyl group, and a linear C 3-40 haloalkyl group.
  • product formation can be monitored by spectroscopic means, such as nuclear magnetic resonance spectroscopy (NMR, e.g., 1 H or 13 C), infrared spectroscopy (IR), spectrophotometry (e.g., UV-visible), mass spectrometry (MS), or by chromatography such as high pressure liquid chromatography (HPLC), gas chromatography (GC), gel-permeation chromatography (GPC), or thin layer chromatography (TLC).
  • NMR nuclear magnetic resonance spectroscopy
  • IR infrared spectroscopy
  • spectrophotometry e.g., UV-visible
  • MS mass spectrometry
  • chromatography such as high pressure liquid chromatography (HPLC), gas chromatography (GC), gel-permeation chromatography (GPC), or thin layer chromatography (TLC).
  • HPLC high pressure liquid chromatography
  • GC gas chromatography
  • GPC gel-permeation chromatography
  • TLC thin layer chromatography
  • Suitable solvents typically are substantially nonreactive with the reactants, intermediates, and/or products at the temperatures at which the reactions are carried out, i.e., temperatures that can range from the solvent's freezing temperature to the solvent's boiling temperature.
  • a given reaction can be carried out in one solvent or a mixture of more than one solvent.
  • suitable solvents for a particular reaction step can be selected.
  • Various compounds according to the present teachings can have good charge transport properties and can be stable under ambient conditions (“ambient stable”), soluble in common solvents, and in turn solution-processable into various articles, structures, or devices.
  • ambient stable compared to other compounds that may have a conjugated core similar to the present compounds, the substituent(s) CHR 1 R 1 ′ and/or CHR 2 R 2 ′ was found to confer greatly improved processability, specifically, in solution-phase at or near room temperature.
  • prior art compounds may require hot solution processing (e.g., temperature at about 100° C.) with aggressive (e.g., chlorinated) solvents
  • the present compounds can be processed at a temperature less than about 50° C. using non-halogenated (e.g., non-chlorinated solvents).
  • organic semiconductor devices that include one or more compounds described herein as semiconductors.
  • organic semiconductor devices include various electronic devices, optical devices, and optoelectronic devices such as thin film transistors (e.g., field effect transistors), photovoltaics, photodetectors, organic light emitting devices such as organic light emitting diodes (OLEDs) and organic light emitting transistors (OLETs), complementary metal oxide semiconductors (CMOSs), complementary inverters, diodes, capacitors, sensors, D flip-flops, rectifiers, ring oscillators, integrated circuits (ICs), radiofrequency identification (RFID) tags, electroluminescent displays, and organic memory devices.
  • thin film transistors e.g., field effect transistors
  • OLEDs organic light emitting diodes
  • OLETs organic light emitting transistors
  • CMOSs complementary metal oxide semiconductors
  • CMOSs complementary inverters
  • diodes diodes
  • capacitors capacitors
  • sensors sensors
  • D flip-flops rectifiers
  • the present teachings provide for a thin film semiconductor including one or more compounds described herein and a field effect transistor device including the thin film semiconductor.
  • the field effect transistor device has a structure selected from top-gate bottom-contact structure, bottom-gate top-contact structure, top-gate top-contact structure, and bottom-gate bottom-contact structure.
  • the field effect transistor device includes a dielectric material, wherein the dielectric material includes an organic dielectric material, an inorganic dielectric material, or a hybrid organic/inorganic dielectric material.
  • the present teachings provide for photovoltaic devices and organic light emitting devices incorporating a thin film semiconductor that includes one or more compounds described herein.
  • compounds of the present teachings generally have good solubility in a variety of common solvents.
  • various embodiments of the present compounds can be processed via inexpensive solution-phase techniques into electronic devices, optical devices, or optoelectronic devices.
  • a compound can be considered soluble in a solvent when at least 1 mg of the compound can be dissolved in 1 mL of the solvent.
  • Examples of common non-chlorinated organic solvents include petroleum ethers; acetonitrile; aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; ketones such as acetone and methyl ethyl ketone; ethers such as tetrahydrofuran, dioxane, bis(2-methoxyethyl) ether, diethyl ether, di-isopropyl ether, and t-butyl methyl ether; alcohols such as methanol, ethanol, butanol, and isopropyl alcohol; aliphatic hydrocarbons such as hexanes; acetates such as methyl acetate, ethyl acetate, methyl formate, ethyl formate, isopropyl acetate, and butyl acetate; amides such as dimethylformamide and dimethylacetamide; sulfoxides such as dimethylsulfoxide
  • compositions that include one or more compounds disclosed herein dissolved or dispersed in a fluid medium, for example, an organic solvent.
  • the composition can further include one or more additives independently selected from detergents, dispersants, binding agents, compatiblizing agents, curing agents, initiators, humectants, antifoaming agents, wetting agents, pH modifiers, biocides, and bactereriostats.
  • surfactants and/or other polymers can be included as a dispersant, a binding agent, a compatiblizing agent, and/or an antifoaming agent.
  • the present compounds can exhibit versatility in their processing.
  • Formulations including the present compounds can be printable via different types of printing techniques including gravure printing, flexographic printing, and inkjet printing, providing smooth and uniform films that allow, for example, the formation of a pinhole-free dielectric film thereon, and consequently, the fabrication of all-printed devices.
  • the present teachings therefore, further provide methods of preparing a semiconductor material.
  • the methods can include preparing a composition that includes one or more compounds disclosed herein dissolved or dispersed in a fluid medium such as a solvent or a mixture of solvents, depositing the composition on a substrate to provide a semiconductor material precursor, and processing (e.g., heating) the semiconductor precursor to provide a semiconductor material (e.g., a thin film semiconductor) that includes one or more compounds disclosed herein.
  • the depositing step can be carried out by printing, including inkjet printing and various contact printing techniques (e.g., screen-printing, gravure printing, offset printing, pad printing, lithographic printing, flexographic printing, and microcontact printing).
  • the depositing step can be carried out by spin coating, drop-casting, zone casting, dip coating, blade coating, or spraying.
  • the depositing step can be carried out at low temperatures, for example, a temperature less than about 50° C., less than about 40° C., or about room temperature. More expensive processes such as vapor deposition also can be used.
  • the present teachings further provide articles of manufacture, for example, composites that include a thin film semiconductor of the present teachings and a substrate component and/or a dielectric component.
  • the substrate component can be selected from doped silicon, an indium tin oxide (ITO), ITO-coated glass, ITO-coated polyimide or other plastics, aluminum or other metals alone or coated on a polymer or other substrate, a doped polythiophene, and the like.
  • the dielectric component can be prepared from inorganic dielectric materials such as various oxides (e.g., SiO 2 , Al 2 O 3 , HfO 2 ), organic dielectric materials such as various polymeric materials (e.g., polycarbonate, polyester, polystyrene, polyhaloethylene, polyacrylate), self-assembled superlattice/self-assembled nanodielectric (SAS/SAND) materials (e.g., as described in Yoon, M-H. et al., PNAS, 102 (13): 4678-4682 (2005), the entire disclosure of which is incorporated by reference herein), as well as hybrid organic/inorganic dielectric materials (e.g., as described in U.S. Pat. No.
  • inorganic dielectric materials such as various oxides (e.g., SiO 2 , Al 2 O 3 , HfO 2 )
  • organic dielectric materials such as various polymeric materials (e.g., polycarbonate, polyester, polystyrene, polyhal
  • the dielectric component can include the crosslinked polymer blends described in U.S. Pat. No. 7,605,394, the entire disclosure of which is incorporated by reference herein.
  • the composite also can include one or more electrical contacts.
  • Suitable materials for the source, drain, and gate electrodes include metals (e.g., Au, Al, Ni, Cu), transparent conducting oxides (e.g., ITO, IZO, ZITO, GZO, GIO, GITO), and conducting polymers (e.g., poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate) (PEDOT:PSS), polyaniline (PANI), polypyrrole (PPy)).
  • metals e.g., Au, Al, Ni, Cu
  • transparent conducting oxides e.g., ITO, IZO, ZITO, GZO, GIO, GITO
  • conducting polymers e.g., poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate) (PEDOT:PSS), polyaniline (PANI), polypyrrole (PPy)).
  • One or more of the composites described herein can be embodied within various organic electronic, optical, and optoelectronic devices such as organic thin film transistors (OTFTs), specifically, organic field effect transistors (OFETs), as well as sensors, capacitors, unipolar circuits, complementary circuits (e.g., inverter circuits), and the like.
  • OFTs organic thin film transistors
  • OFETs organic field effect transistors
  • sensors capacitors
  • unipolar circuits e.g., unipolar circuits
  • complementary circuits e.g., inverter circuits
  • an aspect of the present teachings relates to methods of fabricating an organic field effect transistor that incorporates a semiconductor material of the present teachings.
  • the semiconductor materials of the present teachings can be used to fabricate various types of organic field effect transistors including top-gate top-contact structures, top-gate bottom-contact structures, bottom-gate top-contact structures, and bottom-gate bottom-contact structures.
  • FIG. 1 illustrates the four common types of OFET structures: (a) bottom-gate top-contact structure, (b) bottom-gate bottom-contact structure, (c) top-gate bottom-contact structure, and (d) top-gate top-contact structure.
  • the semiconductor component is in contact with the source and drain electrodes
  • the gate dielectric component is in contact with the semiconductor component on one side and the gate electrode on an opposite side.
  • OTFT devices can be fabricated with one or more compounds disclosed herein on doped silicon substrates, using SiO 2 as the dielectric, in top-contact geometries.
  • the active semiconductor layer which incorporates one or more compounds disclosed herein can be deposited at room temperature or at an elevated temperature.
  • the active semiconductor layer which incorporates one or more compounds disclosed herein can be applied by spin-coating or printing as described herein.
  • metallic contacts can be patterned on top of the films using shadow masks.
  • OTFT devices can be fabricated with one or more compounds disclosed herein on plastic foils, using polymers as the dielectric, in top-gate bottom-contact geometries.
  • the active semiconducting layer which incorporates one or more compounds disclosed herein can be deposited at room temperature or at an elevated temperature.
  • the active semiconducting layer which incorporates one or more compounds disclosed herein can be applied by spin-coating or printing as described herein.
  • Gate and source/drain contacts can be made of Au, other metals, or conducting polymers and deposited by vapor-deposition and/or printing.
  • a semiconducting component incorporating one or more compounds disclosed herein can exhibit p-type semiconducting activity, for example, a hole mobility of 10 ⁇ 4 cm 2 /V-sec or greater and/or a current on/off ratio (I on /I off ) of 10 3 or greater.
  • the present compounds can exhibit broad optical absorption and/or a tuned redox properties and bulk carrier mobilities. Accordingly, the present compounds can be used, for example, as a p-type semiconductor in a photovoltaic design, which includes an adjcaent n-type semiconductor to form a p-n junction.
  • the present compounds can be in the form of a thin film semiconductor, or a composite including the thin film semiconductor deposited on a substrate.
  • the present teachings further provide light emitting transistors including a source electrode, a drain electrode, a gate electrode, a dielectric material and a photoactive component comprising one or more compounds disclosed herein.
  • the compound(s) disclosed herein can be present in a blend material.
  • the photoactive component can be a laminate of two more layers, for example, including a light emitting layer and one or more organic charge transport layers.
  • the present compound(s) can be present in one of the organic charge transport layers, particularly a hole transport layer.
  • 2-methoxy-6-(1-hydroxy-1-methylpentyl)naphthalene (1) n-BuLi (2.5 M in hexanes, 6.2 mL, 15.5 mmol) was added dropwise to a solution of 2-methoxy-6-bromonaphthalene (3.5 g, 14.76 mmol) in THF (120 mL) at ⁇ 78° C. under nitrogen. After stirring at ⁇ 78° C. for 2 h, 2-hexanone (2.19 mL, 17.71 mmol) was added dropwise, and the solution was warmed to room temperature and stirred overnight. The reaction mixture was quenched with water and the organic layer was separated.
  • 2-methoxy-6-(1-methylpentyl)naphthalene (2) To a solution of 2-methoxy-6-(1-hydroxy-1-methylpentyl)naphthalene (1, 0.50 g, 1.935 mmol) in dichloromethane (15 mL) was added triethylsilane (0.35 mL, 2.19 mmol), and the solution was cooled to 0° C. under nitrogen. Then, the solution was treated with trifluoroacetic acid (1.49 mL, 19.34 mmol) dropwise over 30 min. The solution was warmed to room temperature and stirred for 3 h.
  • 2-methoxy-3-methylthio-6-(1-methylpentyl)naphthalene (3) To a solution of 2-methoxy-6-(1-methylpentyl)naphthalene (2, 1.37 g, 5.65 mmol) in THF (25 mL) was added dropwise n-butyllithium (2.5 M in hexanes, 2.49 mL, 6.22 mmol) at ⁇ 78° C. under nitrogen. The solution was stirred at ⁇ 78° C. for 15 min and at room temperature for another 1 h. The solution was then cooled to ⁇ 78° C., and dimethyldisulfide (0.61 mL, 6.88 mmol) was added dropwise.
  • n-butyllithium 2.5 M in hexanes, 2.49 mL, 6.22 mmol
  • the solution was warmed to room temperature and stirred for 15 h.
  • the reaction mixture was quenched with saturated aqueous ammonium chloride solution (50 mL) and extracted with diethyl ether (200 mL).
  • the organic phase was washed with brine, dried over Na 2 SO 4 , concentrated on a rotary evaporator to give the crude compound as a colorless oil.
  • the crude product was purified by column chromatography (silica gel, hexane:dichloromethane (2:1, v/v)) to give 3 as a colorless oil (1.20 g, 74% yield).
  • 6-(1-methylpentyl)-3-methylthio-2-naphthol (4) A solution of BBr 3 in dichloromethane (1.0 M, 3.55 mL, 3.55 mmol) was added dropwise to a solution of 2-methoxy-3-methylthio-6-(1-methylpentyl)naphthalene (3, 0.50 g, 1.73 mmol) in dichloromethane (5 mL) at ⁇ 78° C. under nitrogen. The solution was then warmed to room temperature and stirred for 19 h. The reaction mixture was next poured into ice and the product was extracted with dichloromethane (50 mL).
  • trans-1,2-bis(6-(1-methylpentyl)-3-methylthionaphthalen-2-yl)ethene (6) The reagents 6-(1-methylpentyl)-3-methylthio-2-naphtyl trifluoromethanesulfonate (5, 0.60 g, 1.48 mmol), trans-1,2-bis(tributylstannyl)ethene (0.45 g, 0.74 mmol), and Pd(PPh 3 ) 4 (25.6 mg, 0.022 mmol) were dissolved in dry DMF (20 mL) under nitrogen, and the reaction mixture was heated at 100° C. for 15 hours in dark.
  • the organic phase was separated, washed with brine, dried over Na 2 SO 4 , and concentrated on a rotary evaporator to yield a yellow crude solid.
  • the crude was purified by column chromatography (silica gel, hexane:dichloromethane (4:1, v/v)) followed by recrystallization from hexane to yield 2,9-1MP-DNTT as a yellow crystalline solid (0.31 g, 41% yield).
  • 2-methoxy-6-(1-hydroxy-1-methylbutyl)naphthalene (1) n-BuLi (2.5 M in hexanes, 9.2 mL, 22.9 mmol) was added dropwise to a solution of 2-methoxy-6-bromonaphthalene (5.2 g, 21.85 mmol) in THF (100 mL) at ⁇ 78° C. under nitrogen. After stirring at ⁇ 78° C. for 1 h, 2-pentanone (2.79 mL, 26.22 mmol) was added dropwise, and the solution was warmed to room temperature and stirred overnight. The reaction mixture was quenched with water and the organic layer was separated.
  • 2-methoxy-6-(1-methylbutyl)naphthalene (2) To a solution of 2-methoxy-6-(1-hydroxy-1-methylbutyl)naphthalene (1, 5.34 g, 21.86 mmol) in dichloromethane (120 mL) was added triethylsilane (3.90 mL, 24.70 mmol), and the solution was cooled to 0° C. under nitrogen. Then, the solution was treated with trifluoroacetic acid (16.84 mL, 218.6 mmol) dropwise over 30 min. The solution was warmed to room temperature and stirred overnight.
  • 2-methoxy-3-methylthio-6-(1-methylbutyl)naphthalene (3) To a solution of 2-methoxy-6-(1-methylbutyl)naphthalene (2, 3.00 g, 13.14 mmol) in THF (60 mL) was added dropwise n-butyllithium (2.5 M in hexanes, 5.78 mL, 14.45 mmol) at ⁇ 78° C. under nitrogen. The solution was stirred at ⁇ 78° C. for 15 min and at room temperature for another 1 h. The solution was then cooled to ⁇ 78° C., and dimethyldisulfide (1.40 mL, 15.77 mmol) was added dropwise.
  • n-butyllithium 2.5 M in hexanes, 5.78 mL, 14.45 mmol
  • 6-(1-methylbutyl)-3-methylthio-2-naphthol (4) A solution of BBr 3 in dichloromethane (1.0 M, 18.67 mL, 18.67 mmol) was added dropwise to a solution of 2-methoxy-3-methylthio-6-(1-methylpentyl)naphthalene (3, 2.50 g, 9.11 mmol) in dichloromethane (25 mL) at ⁇ 78° C. under nitrogen. The solution was then warmed to room temperature and stirred for 20 h. The reaction mixture was next poured into ice and the product was extracted with dichloromethane (50 mL).
  • trans-1,2-bis(6-(1-methylbutyl)-3-methylthionaphthalen-2-yl)ethene (6) The reagents 6-(1-methylbutyl)-3-methylthio-2-naphtyl trifluoromethanesulfonate (5, 1.50 g, 3.82 mmol), trans-1,2-bis(tributylstannyl)ethene (1.16 g, 1.91 mmol), and Pd(PPh 3 ) 4 (66.2 mg, 0.057 mmol) were dissolved in dry DMF (50 mL) under nitrogen, and the reaction mixture was heated at 100° C. for 18 hours in dark.
  • Longer alkyl chains are expected to enhance molecular ordering in thin-film phase via alkyl chain interdigitations, which may result in highly crystalline, continuous and uniform film morphologies with enhanced charge transport characteristics. Additionally, longer alkyl chain also ensures good solubility of the semiconductor in common organic solvents for efficient solution-processing.
  • 2-methoxy-3-methylthionaphthalene (1) To a solution of 2-methoxynaphthalene (5.00 g, 31.60 mmol) in THF (30 mL) was added dropwise n-butyllithium (2.5 M in hexanes, 13.91 mL, 34.77 mmol) at ⁇ 78° C. under nitrogen. The solution was stirred at ⁇ 78° C. for 15 min and at room temperature for another 1 h. The solution was then cooled to ⁇ 78° C., and dimethyldisulfide (3.36 mL, 37.88 mmol) was added dropwise. The solution was warmed to room temperature and stirred for 15 h.
  • n-butyllithium 2.5 M in hexanes, 13.91 mL, 34.77 mmol
  • 3-methylthio-2-naphthol (2) A solution of BBr 3 in dichloromethane (1.0 M, 37.10 mL, 37.10 mmol) was added dropwise to a solution of 2-methoxy-3-methylthionaphthalene (1, 3.70 g, 18.11 mmol) in dichloromethane (10 mL) at ⁇ 78° C. under nitrogen. The solution was then warmed to room temperature and stirred for 16 h. The reaction mixture was next poured into ice and the product was extracted with dichloromethane (50 mL).
  • 3-methylthio-2-naphtyl trifluoromethanesulfonate (3) To a solution of 3-methylthio-2-naphthol (2, 3.0 g, 15.77 mmol) and pyridine (4.08 mL, 50.45 mmol) in dichloromethane (40 mL) was added trifluoromethanesulfonic anhydride (3.05 mL, 18.16 mmol) at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 18 h, and then diluted with water (30 mL) and HCl (4M HCl, 30 mL).
  • the organic phase was separated, washed with brine, dried over Na 2 SO 4 , and concentrated on a rotary evaporator to yield a yellow crude solid.
  • the crude was purified by passing through a short plug of silica gel (chloroform as the eluent) followed by a recrystallization from chloroform to yield 2-1MP-DNTT as a yellow solid (20 mg, 16.5% yield).
  • 2-(methylthio)phenyl trifluoromethanesulfonate (1) To a solution of 2-(methylthio)phenol (5.0 g, 35.6 mmol) and pyridine (9.22 mL, 114.1 mmol) in dichloromethane (40 mL) was added trifluoromethanesulfonic anhydride (6.88 mL, 41.0 mmol) at 0° C. under nitrogen. The reaction mixture was stirred at room temperature for 18 h, and then diluted with water (40 mL) and HCl (4M HCl, 40 mL). The organic phase was separated, washed with brine, dried over Na 2 SO 4 , concentrated on a rotary evaporator to give a crude oil product.
  • the organic phase was separated, washed with brine, dried over Na 2 SO 4 , and concentrated on a rotary evaporator to yield a yellow crude solid.
  • the crude was purified by passing through a short plug of silica gel (chloroform as the eluent) followed by a recrystallization from chloroform to yield 1MP-NTTB as a yellow solid (120 mg, 36% yield).
  • C n a linear alkyl chain
  • the solubility of 2,9-1MP-DNTT can be about 50 g/L in toluene at 60° C., which is >500 times higher than those of the corresponding linear alkyl chain DNTT compounds having the same (or lower) number of carbon atoms.
  • BGTC TFTs were fabricated using compounds of the present teachings as the semiconductor layer.
  • OTS octadecyltrichlorosilane
  • Thin films of semiconductors approximately 0-120 nm in thickness were prepared through physical vapor deposition (PVD), with the deposition rate of 0.1-0.5 ⁇ /s and the substrate temperature of 30-120° C.
  • the TFTs were completed by vapor deposition of 300 ⁇ gold source/drain electrodes onto the semiconductor layer through a stencil mask to define the transistor channel.
  • the channel lengths and widths are about 50-200 ⁇ m and about 500-2000 ⁇ m, respectively.
  • the silicon dioxide layer served as the gate insulator.
  • the gate electrode was accessed through an ohmic contact to the doped silicon.
  • TGBC Top Gate Bottom Contact
  • PEN PolyEthyleneNaphthalate
  • ActivInk D1400 Polyera Corp., Skokie, Ill.
  • a silver layer of 30 nm was then deposited by thermal evaporation.
  • Source and drain contacts were patterned using photolithography process and silver was etched by a mixture of acids and water.
  • the semiconductor was spun from a hydrocarbon solution (15 mg-mL) at 2000 rpm.
  • the semiconductor film thickness depends on the solubility of the semiconductor. In the case of 2,9-1MP-DNTT, the film had a thickness of about 60 nm.
  • the amorphous fluoropolymer CYTOP (CTL-809M, Asahi Glass Corporation) was spun as the top-gate dielectric at 5000 rpm to a thickness of about 450 nm, and baked on a hot plate at about 110° C. for 10 minutes.
  • the device structure was completed by the evaporation of an aligned Ag top-gate stripe.
  • BGBC Bottom Gate Bottom Contact
  • FIG. 2 shows representative transfer plots of 2,9-1MP-DNTT-based OTFT devices (top-gate bottom-contact) at different channel lengths (L).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
US13/608,976 2011-09-12 2012-09-10 Compounds Having Semiconducting Properties and Related Compositions and Devices Abandoned US20130062598A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US13/608,976 US20130062598A1 (en) 2011-09-12 2012-09-10 Compounds Having Semiconducting Properties and Related Compositions and Devices
US15/137,939 US9911927B2 (en) 2011-09-12 2016-04-25 Compounds having semiconducting properties and related compositions and devices

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161533785P 2011-09-12 2011-09-12
US13/608,976 US20130062598A1 (en) 2011-09-12 2012-09-10 Compounds Having Semiconducting Properties and Related Compositions and Devices

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US15/137,939 Continuation US9911927B2 (en) 2011-09-12 2016-04-25 Compounds having semiconducting properties and related compositions and devices

Publications (1)

Publication Number Publication Date
US20130062598A1 true US20130062598A1 (en) 2013-03-14

Family

ID=47116279

Family Applications (2)

Application Number Title Priority Date Filing Date
US13/608,976 Abandoned US20130062598A1 (en) 2011-09-12 2012-09-10 Compounds Having Semiconducting Properties and Related Compositions and Devices
US15/137,939 Active US9911927B2 (en) 2011-09-12 2016-04-25 Compounds having semiconducting properties and related compositions and devices

Family Applications After (1)

Application Number Title Priority Date Filing Date
US15/137,939 Active US9911927B2 (en) 2011-09-12 2016-04-25 Compounds having semiconducting properties and related compositions and devices

Country Status (6)

Country Link
US (2) US20130062598A1 (ko)
EP (1) EP2755978A1 (ko)
JP (1) JP6021922B2 (ko)
KR (1) KR20140090979A (ko)
CN (1) CN103958520B (ko)
WO (1) WO2013039842A1 (ko)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015100333A1 (en) 2013-12-24 2015-07-02 Polyera Corporation Support structures for an attachable, two-dimensional flexible electronic device
JPWO2016009890A1 (ja) * 2014-07-18 2017-04-27 富士フイルム株式会社 有機半導体膜形成用組成物、並びに、有機半導体素子及びその製造方法
US9848494B2 (en) 2013-12-24 2017-12-19 Flexterra, Inc. Support structures for a flexible electronic component
US9980402B2 (en) 2013-12-24 2018-05-22 Flexterra, Inc. Support structures for a flexible electronic component
US10121455B2 (en) 2014-02-10 2018-11-06 Flexterra, Inc. Attachable device with flexible electronic display orientation detection
US10254795B2 (en) 2015-05-06 2019-04-09 Flexterra, Inc. Attachable, flexible display device with flexible tail
US10261634B2 (en) 2014-03-27 2019-04-16 Flexterra, Inc. Infrared touch system for flexible displays
US10289163B2 (en) 2014-05-28 2019-05-14 Flexterra, Inc. Device with flexible electronic components on multiple surfaces
US10318129B2 (en) 2013-08-27 2019-06-11 Flexterra, Inc. Attachable device with flexible display and detection of flex state and/or location
US10372164B2 (en) 2013-12-24 2019-08-06 Flexterra, Inc. Flexible electronic display with user interface based on sensed movements
US10459485B2 (en) 2013-09-10 2019-10-29 Flexterra, Inc. Attachable article with signaling, split display and messaging features
US10535325B2 (en) 2014-05-28 2020-01-14 Flexterra, Inc. Low power display updates
US10782734B2 (en) 2015-02-26 2020-09-22 Flexterra, Inc. Attachable device having a flexible electronic component
US11079620B2 (en) 2013-08-13 2021-08-03 Flexterra, Inc. Optimization of electronic display areas
US11086357B2 (en) 2013-08-27 2021-08-10 Flexterra, Inc. Attachable device having a flexible electronic component
US11198698B2 (en) 2016-02-29 2021-12-14 National Institute Of Advanced Industrial Science And Technology Organic semiconductor composition, organic thin film comprising same, and use thereof
US11296289B2 (en) * 2018-06-01 2022-04-05 Samsung Electronics Co., Ltd. Thin film transistor and method of manufacturing the same and thin film transistor panel and electronic device

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6093027B2 (ja) 2012-12-03 2017-03-08 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 有機電子素子用のヘテロアセン化合物
WO2014115749A1 (ja) * 2013-01-22 2014-07-31 日本化薬株式会社 溶液プロセス用有機半導体材料及び有機半導体デバイス
CN106662808A (zh) 2014-02-07 2017-05-10 正交公司 可交联的氟化光聚合物
JP6247560B2 (ja) * 2014-02-20 2017-12-13 富士フイルム株式会社 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料
JP2016001659A (ja) * 2014-06-11 2016-01-07 株式会社東海理化電機製作所 有機半導体材料
EP2978035A1 (en) * 2014-07-24 2016-01-27 E.T.C. S.r.l. Organic electroluminescent transistor
EP2978037A1 (en) * 2014-07-24 2016-01-27 E.T.C. S.r.l. Organic electroluminescent transistor
CN111146352B (zh) 2014-07-24 2022-10-21 飞利斯有限公司 有机电致发光晶体管
KR101928284B1 (ko) 2015-03-23 2018-12-12 닛뽄 가야쿠 가부시키가이샤 유기 화합물, 유기 반도체 재료, 유기 박막 및 그의 제조 방법, 유기 반도체 조성물, 그리고 유기 반도체 디바이스
JP6526585B2 (ja) * 2016-02-29 2019-06-05 日本化薬株式会社 縮合多環芳香族化合物及びその用途
JP6833445B2 (ja) * 2016-10-18 2021-02-24 山本化成株式会社 有機トランジスタ

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090189522A1 (en) * 2004-08-31 2009-07-30 Idernitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device employing the same
JP2009283786A (ja) * 2008-05-23 2009-12-03 Hiroshima Univ 有機半導体組成物
WO2010024388A1 (ja) * 2008-08-29 2010-03-04 出光興産株式会社 有機薄膜トランジスタ用化合物及びそれを用いた有機薄膜トランジスタ
US20100065826A1 (en) * 2006-10-25 2010-03-18 Kazuo Takimiya Novel fused polycyclic aromatic compound, process for producing the same, and use thereof
WO2010098372A1 (ja) * 2009-02-27 2010-09-02 国立大学法人広島大学 電界効果トランジスタ

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006086082A2 (en) 2004-12-23 2006-08-17 Northwestern University Siloxane-polymer dielectric compositions and related organic field-effect transistors
JP4945757B2 (ja) * 2005-01-19 2012-06-06 国立大学法人広島大学 新規な縮合多環芳香族化合物およびその利用
WO2007075748A2 (en) 2005-12-20 2007-07-05 Northwestern University Intercalated superlattice compositions and related methods for modulating dielectric property
CN101529609B (zh) * 2006-10-20 2010-10-20 日本化药株式会社 场效应晶体管
KR20080100982A (ko) 2007-05-15 2008-11-21 삼성전자주식회사 헤테로아센 화합물, 이를 포함하는 유기 박막 및 상기박막을 포함하는 전자 소자
JP5101939B2 (ja) * 2007-07-12 2012-12-19 山本化成株式会社 有機トランジスタ
JP5481850B2 (ja) * 2008-01-23 2014-04-23 東ソー株式会社 ヘテロアセン誘導体、その前駆化合物及びそれらの製造方法
JP5487655B2 (ja) * 2008-04-17 2014-05-07 株式会社リコー ［１］ベンゾチエノ［３，２‐ｂ］［１］ベンゾチオフェン化合物およびその製造方法、それを用いた有機電子デバイス
JP2009302328A (ja) * 2008-06-13 2009-12-24 Nippon Kayaku Co Ltd 有機トランジスタ、およびこれが用いられた有機半導体素子
RU2012104635A (ru) * 2009-07-10 2013-08-20 Сумитомо Кемикал Компани, Лимитед Соединение замещенного бензохалькогенацена, тонкая пленка, включающая такое соединение, и органическое полупроводниковое устройство, включающее такую тонкую пленку
JP5655301B2 (ja) * 2009-12-22 2015-01-21 東ソー株式会社 有機半導体材料
US8643001B2 (en) 2010-12-23 2014-02-04 Samsung Electronics Co. Ltd. Semiconductor composition

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090189522A1 (en) * 2004-08-31 2009-07-30 Idernitsu Kosan Co., Ltd. Aromatic amine derivative and organic electroluminescence device employing the same
US20100065826A1 (en) * 2006-10-25 2010-03-18 Kazuo Takimiya Novel fused polycyclic aromatic compound, process for producing the same, and use thereof
JP2009283786A (ja) * 2008-05-23 2009-12-03 Hiroshima Univ 有機半導体組成物
WO2010024388A1 (ja) * 2008-08-29 2010-03-04 出光興産株式会社 有機薄膜トランジスタ用化合物及びそれを用いた有機薄膜トランジスタ
US20110210319A1 (en) * 2008-08-29 2011-09-01 Compound For Organic Thin Flim Transistor And Organic Than Flim Transitor Using The Same Compound for organic thin film transistor and organic thin film transistor using the same
WO2010098372A1 (ja) * 2009-02-27 2010-09-02 国立大学法人広島大学 電界効果トランジスタ
US20110303910A1 (en) * 2009-02-27 2011-12-15 Nippon Kayaku Kabushiki Kaisha Field Effect Transistor

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Machine translation of JP2009-283786. Date of publication: 7/30/2009. *

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11079620B2 (en) 2013-08-13 2021-08-03 Flexterra, Inc. Optimization of electronic display areas
US10318129B2 (en) 2013-08-27 2019-06-11 Flexterra, Inc. Attachable device with flexible display and detection of flex state and/or location
US11086357B2 (en) 2013-08-27 2021-08-10 Flexterra, Inc. Attachable device having a flexible electronic component
US10459485B2 (en) 2013-09-10 2019-10-29 Flexterra, Inc. Attachable article with signaling, split display and messaging features
US10143080B2 (en) 2013-12-24 2018-11-27 Flexterra, Inc. Support structures for an attachable, two-dimensional flexible electronic device
US9980402B2 (en) 2013-12-24 2018-05-22 Flexterra, Inc. Support structures for a flexible electronic component
WO2015100333A1 (en) 2013-12-24 2015-07-02 Polyera Corporation Support structures for an attachable, two-dimensional flexible electronic device
US10201089B2 (en) 2013-12-24 2019-02-05 Flexterra, Inc. Support structures for a flexible electronic component
US10834822B2 (en) 2013-12-24 2020-11-10 Flexterra, Inc. Support structures for a flexible electronic component
US9848494B2 (en) 2013-12-24 2017-12-19 Flexterra, Inc. Support structures for a flexible electronic component
US10372164B2 (en) 2013-12-24 2019-08-06 Flexterra, Inc. Flexible electronic display with user interface based on sensed movements
US9560751B2 (en) 2013-12-24 2017-01-31 Polyera Corporation Support structures for an attachable, two-dimensional flexible electronic device
US10121455B2 (en) 2014-02-10 2018-11-06 Flexterra, Inc. Attachable device with flexible electronic display orientation detection
US10621956B2 (en) 2014-02-10 2020-04-14 Flexterra, Inc. Attachable device with flexible electronic display orientation detection
US10261634B2 (en) 2014-03-27 2019-04-16 Flexterra, Inc. Infrared touch system for flexible displays
US10289163B2 (en) 2014-05-28 2019-05-14 Flexterra, Inc. Device with flexible electronic components on multiple surfaces
US10535325B2 (en) 2014-05-28 2020-01-14 Flexterra, Inc. Low power display updates
US10062851B2 (en) 2014-07-18 2018-08-28 Fujifilm Corporation Composition for forming organic semiconductor film, organic semiconductor element, and method for manufacturing organic semiconductor element
EP3171420A4 (en) * 2014-07-18 2017-07-05 Fujifilm Corporation Organic semiconductor film formation composition, organic semiconductor element, and production method therefor
JPWO2016009890A1 (ja) * 2014-07-18 2017-04-27 富士フイルム株式会社 有機半導体膜形成用組成物、並びに、有機半導体素子及びその製造方法
US10782734B2 (en) 2015-02-26 2020-09-22 Flexterra, Inc. Attachable device having a flexible electronic component
US10254795B2 (en) 2015-05-06 2019-04-09 Flexterra, Inc. Attachable, flexible display device with flexible tail
US11198698B2 (en) 2016-02-29 2021-12-14 National Institute Of Advanced Industrial Science And Technology Organic semiconductor composition, organic thin film comprising same, and use thereof
US11296289B2 (en) * 2018-06-01 2022-04-05 Samsung Electronics Co., Ltd. Thin film transistor and method of manufacturing the same and thin film transistor panel and electronic device

Also Published As

Publication number Publication date
JP6021922B2 (ja) 2016-11-09
US9911927B2 (en) 2018-03-06
US20160351832A1 (en) 2016-12-01
JP2014531435A (ja) 2014-11-27
KR20140090979A (ko) 2014-07-18
EP2755978A1 (en) 2014-07-23
CN103958520A (zh) 2014-07-30
CN103958520B (zh) 2017-03-22
WO2013039842A1 (en) 2013-03-21

Similar Documents

Publication Publication Date Title
US9911927B2 (en) Compounds having semiconducting properties and related compositions and devices
US8022214B2 (en) Organic semiconductor materials and precursors thereof
EP2240970B1 (en) Perylene semiconductors and methods of preparation and use thereof
US8569501B2 (en) Semiconductor materials and methods of preparation and use thereof
US8440828B2 (en) Organic semiconductors and devices incorporating same
US9175212B2 (en) Organic semiconductors
US8710225B2 (en) Thiocyanato or isothiocyanato substituted naphthalene diimide and rylene diimide compounds and their use as n-type semiconductors
US9006725B2 (en) Dithienophthalimide semiconductor polymers
US10535822B2 (en) Molecular and polymeric semiconductors and related devices
US9067886B2 (en) Compounds having semiconducting properties and related compositions and devices
US9147850B2 (en) Perylene-based semiconductors and methods of preparation and use thereof
US8598575B2 (en) Semiconducting compounds and related compositions and devices
US9312501B2 (en) Semiconducting compounds and optoelectronic devices incorporating same
US8859714B1 (en) Polymeric semiconductors and related devices
US8513445B2 (en) Polycyclic aromatic molecular semiconductors and related compositions and devices
US8993711B2 (en) Semiconducting polymers and optoelectronic devices incorporating same
US9812645B2 (en) Perylene-based semiconductors
WO2016071140A1 (en) Phenacene compounds for organic electronics
US8987447B2 (en) Thienopyrazine compound and field effect transistor containing the same

Legal Events

Date Code Title Description
AS Assignment

Owner name: POLYERA CORPORATION, ILLINOIS

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:USTA, HAKAN;BOUDINET, DAMIEN;QUINN, JORDAN;AND OTHERS;SIGNING DATES FROM 20121213 TO 20130103;REEL/FRAME:030599/0001

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION