WO2016071140A1 - Composés phénacène pour l'électronique organique - Google Patents

Composés phénacène pour l'électronique organique Download PDF

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WO2016071140A1
WO2016071140A1 PCT/EP2015/074756 EP2015074756W WO2016071140A1 WO 2016071140 A1 WO2016071140 A1 WO 2016071140A1 EP 2015074756 W EP2015074756 W EP 2015074756W WO 2016071140 A1 WO2016071140 A1 WO 2016071140A1
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mmol
compounds
organic
solution
printing
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PCT/EP2015/074756
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English (en)
Inventor
Chongjun JIAO
Thomas Weitz
Michael EUSTACHI
Sweemeng Ang
Fabien Nekelson
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Basf Se
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    • 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
    • H10K85/6576—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]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the invention relates to phenacene compounds and their use.
  • Organic semiconducting materials can be used in electronic devices such as organic photovoltaic (OPV) cells, organic field-effect transistors (OFETs) and organic light emitting diodes (OLEDs).
  • OCV organic photovoltaic
  • OFETs organic field-effect transistors
  • OLEDs organic light emitting diodes
  • organic semiconducting materials are compatible with liquid processing techniques such as spin coating, solution casting or printing.
  • Liquid processing techniques are convenient from the point of processability, and can also be applied to plastic substrates.
  • organic semiconducting materials which are compatible with liquid processing techniques allow the production of low cost, light weight and, optionally also flexible, electronic devices, which is a clear advantage of these organic semiconducting materials compared to inorganic semiconducting materials.
  • the organic semiconducting materials are stable, in particular towards oxidation.
  • the organic semiconducting materials When used in organic field-effect transistors (OFETs), the organic semiconducting materials should show a high charge carrier mobility and a high on/off ratio.
  • OFETs organic field effect transistors
  • JP2009/063846 discloses alkylated picene for solution-based OFETs with a charge carrier mobility of up to 2 cm 2 V- 1 S "1 .
  • R is H, n-C8Hi 7 or phenyl
  • OFETs organic field effect transistors
  • OFETs show the following charge carrier mobilities: 1 .2 (compound 1 ), 1 .8 (compound 2), 2.0 (compound 3), 1 .7 (compound 4) cm 2 V -1 s _1 , and the following on-off ratios: 2 x 10 6 (compound 1 ), 3 x 10 6 (compound 2), 4 x 10 6 (compound 3) and 3 x 10 6 (compound 4).
  • One of the OFETs shows a charge carrier mobility of 3.1 cm V -1 s _1 and an on/off ratio of 10 5 .
  • WO 2013/168048 A1 discloses phenacene compounds of the general formula
  • one of groups a, b and c is X and the other two groups are C-R 1 and C-R 2 , respectively, one of groups d, e and f is X and the other two groups are C-R 5 and C-R 6 , respectively, wherein X are, independently of each other, selected from the group consisting of NH, O, S and Se, preferably selected from the group consisting of O, S and Se, more preferably selected from the group consisting of O and S, and particular preferably are S,
  • R 1 - R 10 are independently of each other H, halogene, -CN, -NO2 or a linear or branched, saturated or unsaturated C1-C40 hydrocarbon residue, which can be substituted 1 - to 5-fold with halogene (F, CI, Br, I), -OR a , -NR a 2, -CN and/or -NO2, and wherein one or more Chb-groups can be replaced by -0-, -S-, -NR b -, -OC(O)- or -C(O)-, and wherein R a and R b are independently of each other H, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C1-C30 haloalkyl, C2-C30 haloalkenyl, C2-C30 haloalkynyl or C2-C30 acyl.
  • R 1 , R 2 , R 5 and R 6 are selected from the group consisting of H, halogen (F, CI, Br, I), and a C1-20 alkyl group.
  • R 3 , R 4 are selected from the group consisting of H, halogen (F, CI, Br, I), and a C1-20 alkyl group.
  • R 7 , R 8 , R 9 , R 10 are selected from the group consisting of H, halogen atom and C1-20 alkyl groups.
  • R 1 , R 5 are alkyl, in particular n-tetradecyl.
  • R 1 and R 2 are independently of each other a linear or branched C1-20 alkyl group.
  • the phenacene compounds of the present invention have particular good semiconducting activity. Materials prepared from these compounds have demonstrated unexpected properties. It has been discovered that compounds of the present invention have exceptionally high carrier mobility and/or good current modulation characteristics in field-effect devic- es (e.g., thin-film transistors). In addition, it has been discovered that compounds of the present invention possess certain processing advantages compared to related representative compounds such as better solubility to permit solution-processability and/or good stability at ambient conditions, for example, air stability. Further, the compounds can be embedded with other components for utilization in a variety of semiconductor-based devices.
  • R 1 and R 2 can be linear or branched C1-C20 alkyl.
  • Examples are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tert. -butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, 1 ,1 ,3,3-tetramethylpentyl, n-hexyl, 1 -methylhexyl, 1 ,1 ,3,3,5,5-hexamethylhexyl, n-heptyl, isoheptyl, 1 ,1 ,3,3-tetramethylbutyl, 1 -methylheptyl, 3- methylheptyl, n-octyl, 1 ,1 ,3,3-tetramethylbutyl and 2-ethylhexyl, n-nonyl, decyl, undecyl, do- decyl, tridecyl
  • R 1 and R 2 are independently of each other a linear or branched C6- CM alkyl group.
  • R 1 and R 2 are selected from the group consisting of n-hexadecyl, n-tetradecyl, n-dodecyl, n-decyl, n-octyl, n-hexyl and 1 -methylpentyl.
  • R 1 and R 2 are the same alkyl group. However, R 1 and R 2 can be different alkyl groups.
  • R alkyl
  • the present invention can offer processing advantages in fabricating electrical devices such as thin film semiconductors, field-effect devices, organic light emitting diodes (OLEDs), organic photovoltaics, photodetec- tors, capacitors, and sensors.
  • electrical devices such as thin film semiconductors, field-effect devices, organic light emitting diodes (OLEDs), organic photovoltaics, photodetec- tors, capacitors, and sensors.
  • OLEDs organic light emitting diodes
  • a compound can be considered soluble in a sol- vent when at least 1 mg of the compound can be dissolved in 1 ml. of the solvent.
  • Examples of common 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-/sopropyl ether, and f-butyl methyl ether; alcohols such as methanol, ethanol, butanol, and /sopropyl alco- hoi; aliphatic hydrocarbons such as hexanes; acetates such as methyl acetate, ethyl acetate, methyl formate, ethyl formate, isopropyl acetate, and butyl acetate; amides such as dimethyl- formamide and dimethylacetamide; sulfoxides such as dimethylsul
  • the present invention further provides compositions that include one or more compounds of formula (I) disclosed herein dissolved or dispersed in a liquid medium, for example, an organic solvent, an inorganic solvent, or combinations thereof (e.g., a mixture of organic solvents, inorganic solvents, or organic and inorganic solvents).
  • the composition can further include one or more additives independently selected from detergents, dis- persants, binding agents, compatibilizing agents, curing agents, initiators, humectants, anti- foaming agents, wetting agents, pH modifiers, biocides, and bactereriostats.
  • sur- factants and/or other polymers can be included as a disper- sant, a binding agent, a compatibilizing agent, and/or an antifoaming agent.
  • such compositions can include one or more compounds disclosed herein, for example, two or more different compounds of the present invention can be dissolved in an organic solvent to prepare a composition for deposition.
  • the composition can include two or more regioisomers.
  • the devices described herein also can comprise one or more compounds of the present invention, for example, two or more regioisomers as described herein.
  • Various deposition techniques including various solution-processing techniques, have been used in preparing organic electronics. For example, much of the printed electronics technology has focused on inkjet printing, primarily because this technique offers greater control over feature position and multilayer registration. Inkjet printing is a noncontact process, which offers the benefits of not requiring a preformed master (compared to contact printing techniques), as well as digital control of ink ejection, thereby providing drop-on-demand printing. Micro dispensing is another non-contact method of printing. However, contact printing techniques have the key advantage of being well-suited for very fast roll-to-roll processing.
  • Exemplary contact printing techniques include, but are not limited to, screen-printing, gravure printing, offset printing, flexo- graphic printing, lithographic printing, pad printing, and microcontact printing.
  • printing includes a noncontact process, for example, inkjet printing, micro dispensing, and the like, and a contact process, for example, screen-printing, gravure printing, offset printing, flexo- graphic printing, lithographic printing, pad printing, microcontact printing, and the like.
  • Other solution processing techniques include, for example, spin coating, drop-casting, zone casting, dip coating, blade coating, or spraying.
  • the deposition step can be carried out by vacuum vapor-deposition.
  • the present invention therefore, further provide methods of preparing a semiconductor material.
  • the methods can include preparing a composition that includes one or more compounds of formula (I) disclosed herein dissolved or dispersed in a liquid medium such as a solvent or a mixture of solvents, and depositing the composition on a substrate to provide a semiconductor material (e.g., a thin film semiconductor) that includes one or more compounds of formula (I) disclosed herein.
  • the liquid medium can be an organic solvent, an inorganic solvent such as water, or combinations thereof.
  • the composition can further include one or more additives independently selected from viscosity modulators, detergents, dispersants, binding agents, compatibilizing agents, curing agents, initiators, hu- mectants, antifoaming agents, wetting agents, pH modifiers, biocides, and bactereriostats.
  • additives independently selected from viscosity modulators, detergents, dispersants, binding agents, compatibilizing agents, curing agents, initiators, hu- mectants, antifoaming agents, wetting agents, pH modifiers, biocides, and bactereriostats.
  • surfactants and/or polymers e.g., polystyrene, polyethylene, poly-alpha-methyl- styrene, polyisobutene, polypropylene, polymethylmethacrylate, and the like
  • dispersant e.g., polystyrene, polyethylene, poly-alpha-methyl- styrene, polyisobutene,
  • 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.
  • Various articles of manufacture including electronic devices, optical devices, and optoelectronic devices such as field effect transistors (e.g., thin film transistors), photovoltaics, organic light emitting diodes (OLEDs), complementary metal oxide semiconductors (CMOSs), complemen- tary inverters, D flip-flops, rectifiers, and ring oscillators, that make use of the compounds and the semiconductor materials disclosed herein also as well as methods of making the same are within the scope of the present invention.
  • field effect transistors e.g., thin film transistors
  • OLEDs organic light emitting diodes
  • CMOSs complementary metal oxide semiconductors
  • complemen- tary inverters e.g., D flip-flops, rectifiers, and ring oscillators
  • the present invention provides articles of manufacture such as the various devices described herein that include a composite having a semiconductor material of the present invention comprising compound of formula (I), a substrate component, and/or a dielectric component.
  • the substrate component can be selected from materials including 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 or other poly- mers, and the like.
  • the dielectric component can be prepared from inorganic dielectric materials such as various oxides (e.g., S1O2, AI2O3, Hf02), organic dielectric materials such as various polymeric materials (e.g., polycarbonate, polyester, polystyrene, polyhaloethylene, polyacry- late), self-assembled superlattice/self-assembled nanodielectric (SAS/SAND) materials (e.g., described in Yoon, M-H. et al., PNAS, 102 (13): 4678-4682 (2005), the entire disclosure of which is incorporated by reference herein), and hybrid organic/inorganic dielectric materials (e.g., described in U.S. Patent Application Serial No. 1 1/642,504, the entire disclosure of which is incorporated by reference herein).
  • the dielectric component can include the crosslinked polymer blends described in U.S. Patent Application Serial Nos.
  • 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)).
  • One or more of the composites described herein can be incorporated 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, complementary circuits (e.g., inverter circuits), and the like.
  • An aspect of the present invention therefore, relates to methods of fabricating an organic field effect transistor that incorporates a semiconductor material of the present invention comprising compounds of formula (I).
  • the semiconductor materials of the present invention can be used to fabricate various types of organic field effect transistors including top-gate top-contact capacitor structures, top-gate bottom-contact capacitor structures, bottom-gate top-contact capacitor structures, and bottom-gate bottom-contact capacitor structures.
  • OTFT devices can be fabricated with the present compounds of formula (I) on doped silicon substrates, using S1O2 as the dielectric, in top-contact geometries.
  • the active semiconducting layer which incorporates at least a compound of the present invention can be deposited by vacuum vapor deposition at room temperature or at an elevated temperature.
  • the active semiconducting layer which incorporates at least a compound of the present invention can be applied by solution-based process, for example, spin-coating or jet printing.
  • metallic contacts can be patterned on top of the films using shadow masks.
  • OTFT devices can be fabricated with the present compounds of formula (I) on plastic foils, using polymers as the dielectric, in top-gate bottom-contact geometries.
  • the active semiconducting layer which incorporates at least a compound of the present invention can be deposited at room temperature or at an elevated temperature.
  • the active semiconducting layer which incorporates at least a compound of the present invention 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. Other articles of manufacture in which compounds of formula (I) of the present invention are useful as photovoltaics or solar cells.
  • the compounds of formula (I) described herein can be used as a p-type semiconductor in a photovoltaic design, which includes an adjacent n-type semiconduct- ing material that forms a p-n junction.
  • the compounds can be in the form of a thin film semiconductor, which can be a composite of the thin film semiconductor deposited on a substrate. Exploitation of compounds of the present invention in such devices is within the knowledge of the skilled artisan.
  • another aspect of the present invention relates to methods of fabricating an organic light-emitting transistor, an organic light-emitting diode (OLED), or an organic photovoltaic device that incorporates one or more semiconductor materials of the present invention.
  • OLED organic light-emitting diode
  • OLED organic photovoltaic device
  • iPrMgCI (2M, 77 mL, 153 mmol) was added drop wise to a solution of 2,3-dibromo-1 ,4-diiodo- benzene at -78 °C over 45 min and the resultant mixture stirred at -78 °C for 3 h.
  • 2-lsopropoxy- 4,4, 5, 5-tetramethyl-1 ,3,2-dioxaborolane 38 g, 42 mL, 205 mmol was added drop wise to the stirring mixture at -78 °C over 30 minutes the resultant reaction mixture was stirred at room temperature for 16 h.
  • a commercial LDA solution (2 M, 24 ml, 47 mmol) was diluted in THF (65 ml) solution at 0 °C.
  • a solution of 2-bromo-5-tetradecylthiophene (14 g, 39 mmol) in THF (65 ml) was added drop wise to the dilute LDA solution at 0 °C over 60 mins using a dropping funnel.
  • the resultant mixture was gradually warmed to room temperature and stirred for 3 hrs.
  • the reaction mixture was quenched with water (150 ml) and extracted with Et.20 (2 x 100 ml).
  • n-BuLi (1.6 M, 24.4 mL, 39 mmol) was added dropwise to a solution of ethynyltrimethylsilane (4.0 g, 41 mmol) in THF (40 mL) at -78 °C and gradually warmed to 0 °C over 30 min.
  • the reaction mixture was cooled to -78 °C again and tributyltin chloride (1 1.4 mL, 39 mmol) in THF (30 mL) was added dropwise to the resultant mixture.
  • the reaction mixture was stirred for 18 h at room temperature and quenched with water (20 mL).
  • Tetrakis(triphenylphosphine)palladium(0) (1.8 g, 1.47 mmol) was added to a solution of 2-[2,3- dibromo-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1 ,3,2- dioxaborolane (7.2 g, 14.76 mmol), 3-bromo-5-tetradecylthiophene (16.53 g, 46 mmol) and aqueous sodium carbonate solution (2M, 32 mL, 65 mmol) in DME (64 mL) and stirred at 100 °C for 6 h.
  • Tetrakis(triphenylphosphine)palladium(0) (1 .3 g, 0.95 mmol) was added to a solution of trime- thyl-tributylstannanylethynyl-silane (1 1 .1 g, 28.5 mmol) and 2,3-dibromo-1 ,4-bis(5-tetradecyl- thiophen-2-yl) benzene (7.5 g, 9.5 mmol) in toluene (100 mL) and stirred at 100 °C for 3 h. The reaction mixture was cooled to room temperature and diluted with aqueous saturated ammonium chloride solution (100 mL).
  • Tetrabutylammonium fluoride (1 M, 23 ml_, 22.8 mmol) was added to a solution of 2,3- bis(ethynyltrimethylsilane)-1 ,4-bis(5-tetradecyl-thiophen-2-yl)benzene (7.86 g, 9.5 mmol) at room temperature and the reaction was stirred for 1 h.
  • the reaction mixture was diluted with aqueous saturated ammonium chloride solution (100 ml_).
  • the mixture was extracted with diethyl ether (3 x 50 ml_).
  • the combined organic phases were dried and concentrated to give brown solids, which were purified by column chromatography to yield brown solids (3.6 g, 55%).
  • W(CO) 5 (THF) (3.0 g, 8.5 mmol) was formed by irradiating W(CO) 6 in THF (75ml_) under UVA lamp at 60 °C for 2 h where the colorless reaction mixture turns to yellow-green after 2 h.
  • the solution of W(CO)5(THF) in THF was transferred quickly into a flask of stirring 2,3-diethynyl-1 ,4- bis(5-tetradecyl-thiophen-2-yl)benzene in THF (50ml_) at room temperature and the reaction mixture stirred for 48 h in the dark.
  • Examples 12-16 Compounds 2, 3, 4, 5 and 6 were synthesized in the same way as described above.
  • n-BuLi 1.6 M, 96 mL, 154 mmol
  • 2-bromothiophene 25.0 g, 154 mmol
  • 2-Hexanone 17 mL, 139 mmol
  • THF 50 mL
  • the reaction mixture was warmed to room temperature and quenched with saturated aqueous ammonium chloride solution (200 mL) and extracted with diethyl ether (3 x 100 mL).
  • N-Bromosuccinimide (16 g, 82 mmol) was added portion wise (4 x 4 g portions) to a stirring solution of 2-(1 -methylpentyl)thiophene (13.6 g, 81 mmol) at 0 °C over 40 min at 10-minute inter- vals and stirred for 90 min at room temperature.
  • the reaction was completed by 1 H NMR analysis and water (100 mL) was added.
  • the resultant mixture was extracted with methylene chloride (3 x 75 mL).
  • the combined organic phases were dried over MgSC , filtered and concentrated to give the crude product.
  • the crude product was purified by column chromatography on silica gel using 100% hexanes to yield red oil (14.0 g, 70%).
  • LDA solution (2 M, 57 ml, 1 14 mmol) was diluted in THF (90 ml) solution at 0 °C.
  • the resultant mixture was gradually warmed to room temperature and stirred for 3 hrs.
  • the reaction mixture was quenched with water (100 ml) and extracted with Et.20 (3 x 75 ml).
  • Tetrakis(triphenylphosphine)palladium(0) (2.8 g, 2.5 mmol) was added to a solution of 2-[2,3- dibromo-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1 ,3,2- dioxaborolane (12 g, 25.0 mmol), 4-bromo-2-(1 -methylpentyl)thiophene (14.8 g, 60 mmol) and aqueous sodium carbonate solution (2M, 50 mL, 1 10 mmol) in DME (100 mL) and stirred at 100 °C for 6 h.
  • 2-[2,3- dibromo-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1 ,3,2- dioxaborolane (12 g, 25.0
  • Tetrakis(triphenylphosphine)palladium(0) (1 .9 g, 1.7 mmol) was added to a solution of 2,3- dibromo-1 ,4-bis[5-(1 -methylpentyl)thiophen-2-yl]benzene (9.7 g, 17 mmol)and trimethyl- tributylstannanylethynyl-silane (15.8 g, 40.8 mmol) in toluene (90 mL) and stirred at 100 °C for 3 h. The reaction mixture was cooled to room temperature and diluted with aqueous saturated ammonium chloride solution (90 mL).
  • Tetrabutylammonium fluoride solution in THF (1 M, 45 ml_, 47.6 mmol) was added to a solution of 2,3-bis(ethynyltrimethylsilane)-1 ,4-bis[5-(1 -methylpentyl)thiophen-2-yl]benzene (10.25 g, 9.5 mmol) in THF (50 ml.) at room temperature and the reaction was stirred for 3 h. The reaction mixture was diluted with aqueous saturated ammonium chloride solution (50 ml_). The mixture was extracted with diethyl ether (3 x 50 ml_).
  • W(CO) 5 (THF) was formed by irradiating W(CO) 6 (1 .8 g, 2.6 mmol) in THF (75ml_) under UVA lamp at 60 °C for 2 h where the colorless reaction mixture turns to yellow-green after 2 h.
  • the solution of W(CO)5(THF) in THF was transferred quickly into a flask of stirring 2,3-diethynyl-1 ,4- bis[5-(1 -methylpentyl)thiophen-2-yl]benzene (3.0 g, 12.9 mmol) in THF (50ml_) at room temperature and the reaction mixture stirred for 48 h in the dark.
  • reaction mixture was concentrated in vacuo and the resultant residue redissolved in warm hexanes (30 °C) and wet loaded onto silica gel column. Column chromatography using 100% hexanes gave a crude product. The crude product was recrystallized from ethanol and then subjected to sublimation to give pale yellow solids (380 mg, 12%).
  • Figures 1A, 2A and 3A show the respective output characteristics of vacuum deposited OFETs for compounds 1 , 2, and 7. In these figures, the drain current is plotted against the drain-source voltage.
  • Figures 1 B, 2B and 3B show the transfer characteristics for these compounds, respectively. In these figures, the drain current is plotted against the gate-source voltage.

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  • 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)

Abstract

La présente invention concerne des composés phénancène de formule (I) dans laquelle R1 et R2 sont indépendamment l'un de l'autre un groupe alkyle en C1-20 linéaire ou ramifié.
PCT/EP2015/074756 2014-11-04 2015-10-26 Composés phénacène pour l'électronique organique WO2016071140A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109791983A (zh) * 2016-09-29 2019-05-21 富士胶片株式会社 微晶有机半导体膜、有机半导体晶体管及有机半导体晶体管的制造方法
CN111892696A (zh) * 2020-07-23 2020-11-06 华南理工大学 一种二噻吩并苯稠环喹喔啉共轭聚合物及其制备方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013168048A1 (fr) * 2012-05-07 2013-11-14 Basf Se Composés de phénacène pour composants électroniques organiques
JP2014139143A (ja) * 2013-01-21 2014-07-31 Idemitsu Kosan Co Ltd ジチエノフェナントレン化合物、当該化合物を含む有機薄膜トランジスタ用組成物、及び有機薄膜トランジスタ
WO2014148614A1 (fr) * 2013-03-22 2014-09-25 富士フイルム株式会社 Transistor à couches minces organiques

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013168048A1 (fr) * 2012-05-07 2013-11-14 Basf Se Composés de phénacène pour composants électroniques organiques
JP2014139143A (ja) * 2013-01-21 2014-07-31 Idemitsu Kosan Co Ltd ジチエノフェナントレン化合物、当該化合物を含む有機薄膜トランジスタ用組成物、及び有機薄膜トランジスタ
WO2014148614A1 (fr) * 2013-03-22 2014-09-25 富士フイルム株式会社 Transistor à couches minces organiques

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 201457, Derwent World Patents Index; AN 2014-N95229, XP002735248 *
DATABASE WPI Week 201470, Derwent World Patents Index; AN 2014-R60475, XP002735247 *
Y. NISHIHARA ET AL.: "Phenanthro[1,2-b:8,7-b']dithiophene: a new picene-type molecule for transistor applications", RSC ADVANCES, vol. 3, no. 42, 12 August 2013 (2013-08-12), pages 19341 - 19347, XP002735249, ISSN: 2046-2069, Retrieved from the Internet <URL:http://pubs.rsc.org/en/Content/ArticleLanding/2013/RA/c3ra44050h#!divAbstract> [retrieved on 20150128], DOI: 10.1039/c3ra44050h *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109791983A (zh) * 2016-09-29 2019-05-21 富士胶片株式会社 微晶有机半导体膜、有机半导体晶体管及有机半导体晶体管的制造方法
CN109791983B (zh) * 2016-09-29 2023-06-16 富士胶片株式会社 微晶有机半导体膜、有机半导体晶体管及其制造方法
CN111892696A (zh) * 2020-07-23 2020-11-06 华南理工大学 一种二噻吩并苯稠环喹喔啉共轭聚合物及其制备方法和应用

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