WO2011102390A1 - Composé aromatique, film mince organique l'utilisant, et élément de film mince organique pourvu de ce film mince organique - Google Patents

Composé aromatique, film mince organique l'utilisant, et élément de film mince organique pourvu de ce film mince organique Download PDF

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WO2011102390A1
WO2011102390A1 PCT/JP2011/053287 JP2011053287W WO2011102390A1 WO 2011102390 A1 WO2011102390 A1 WO 2011102390A1 JP 2011053287 W JP2011053287 W JP 2011053287W WO 2011102390 A1 WO2011102390 A1 WO 2011102390A1
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thin film
organic thin
aromatic compound
formula
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三浦　雅博
淳 熊谷
康次 平野
佐藤　哲也
上田　将人
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住友化学株式会社
国立大学法人大阪大学
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic 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
    • 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
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • the present invention relates to an aromatic compound, an organic thin film using the same, an organic thin film element including the organic thin film, an organic thin film transistor, and an organic photoelectric conversion element.
  • An organic thin film containing an organic semiconductor material having a charge (meaning electron or hole, hereinafter the same) transportability is expected to be applied to organic thin film elements such as organic thin film transistors, organic solar cells, and optical sensors.
  • organic thin film elements such as organic thin film transistors, organic solar cells, and optical sensors.
  • organic p-type semiconductor materials shown hole transport properties
  • organic n-type semiconductor materials shown electron transport properties
  • a compound having a thiophene ring such as oligothiophene or polythiophene can take a stable radical cation state, and thus is expected to exhibit high hole transportability.
  • oligothiophenes having a long chain length are expected to have higher hole transportability because the conjugation length becomes longer.
  • EDOT ethylenedioxythiophene
  • the present invention has been made in view of such circumstances, and an object of the present invention is to provide an aromatic compound that can be applied as an organic semiconductor material having excellent charge transportability and high stability.
  • Another object of the present invention is to provide an organic thin film obtained by using such an aromatic compound, and an organic thin film element provided with the organic thin film, particularly an organic thin film transistor and an organic photoelectric conversion element.
  • the aromatic compound of the present invention is represented by the formula (1).
  • Ar 11 represents a group forming a conjugated structure with X 11 and X 12 include an aromatic ring
  • X 11 and X 12 independently formula (1a) or (1b)
  • the group represented by these is shown.
  • Ar 12 and Ar 13 each independently represent an aromatic hydrocarbon group having 6 or more carbon atoms
  • R 11 , R 12 , R 13 and R 14 are each independently Represents a hydrogen atom, a halogen atom or a monovalent group
  • X 13 , X 14 , X 15 and X 16 each independently represent an oxygen atom, a sulfur atom or a selenium atom.
  • the aromatic compound of the present invention has a long and high planar conjugated structure as a whole by having a group represented by the formula (1a) or (1b) at the terminal portion. Therefore, when applied as an organic semiconductor material, excellent charge transport properties can be exhibited.
  • the group represented by the formula (1a) or (1b) has an aromatic hydrocarbon group represented by Ar 12 or Ar 13 at a portion located at the end of the conjugated structure.
  • Ar 12 or Ar 13 an aromatic hydrocarbon group represented by Ar 12 or Ar 13 at a portion located at the end of the conjugated structure.
  • the aromatic compound has a stable molecular structure, and the charge transfer as an organic semiconductor material is repeated or a voltage is applied.
  • Ar 11 is preferably a group represented by the formula (2).
  • Ar 21 , Ar 22 and Ar 23 each independently have an aromatic hydrocarbon group having 6 or more carbon atoms which may have a substituent, or have a substituent.
  • Ar 11 is a group having a structure containing only an aromatic hydrocarbon group and / or a heterocyclic group, the conjugation property of the aromatic compound is further increased, and a more excellent charge transport property can be obtained. become.
  • At least one of X 13 and X 14 is preferably a sulfur atom, and at least one of X 15 and X 16 is preferably a sulfur atom.
  • An aromatic compound having such a structure can exhibit further excellent charge transport properties.
  • Ar 12 and Ar 13 are preferably a phenyl group or a naphthyl group. By having these groups at the terminal of the conjugated structure, the aromatic compound can exhibit extremely excellent stability in addition to high charge transportability.
  • Ar 11 is a group represented by the formula (2), and X 13 , X 14 , X 15 and X 16 are sulfur atoms.
  • Ar 12 and Ar 13 are preferably phenyl groups.
  • At least one of Ar 21 , Ar 22 and Ar 23 is preferably a thiophenediyl group which may have a substituent or a thienothiophenediyl group which may have a substituent.
  • the present invention also provides an organic thin film containing the aromatic compound of the present invention, and an organic thin film element comprising such an organic thin film, particularly an organic thin film transistor and an organic photoelectric conversion element. Since the organic thin film of the present invention contains the aromatic compound of the present invention, it is possible to obtain excellent charge transportability and maintain such high charge transportability over a long period of time. Therefore, an organic thin film element such as an organic thin film transistor or an organic photoelectric conversion element provided with such an organic thin film can stably exhibit high charge transportability and has excellent practicality.
  • the aromatic compound applicable as an organic-semiconductor material which has the outstanding charge transport property and has high stability.
  • an organic thin film containing such an aromatic compound and capable of stably exhibiting high charge transportability, and an organic thin film element such as an organic thin film transistor or an organic photoelectric conversion element having such an organic thin film are provided. It becomes possible to provide.
  • the aromatic compound of the present embodiment is a conjugated compound having a structure represented by the above formula (1).
  • the conjugated compound has a structure in which a single bond and an unsaturated bond, a lone electron pair, a radical, or a non-bonding orbital are alternately connected in the main skeleton of a molecule, Refers to a compound that is delocalized.
  • the aromatic compound according to a preferred embodiment has a group that includes an aromatic ring and forms a conjugated structure with X 11 and X 12 as Ar 11 .
  • a group may be any group as long as it has at least one aromatic ring such as an aromatic hydrocarbon ring or an aromatic heterocyclic ring and can form a conjugated structure as a whole compound. Therefore, Ar 11 may be a group that includes a chain structure other than an aromatic ring to form a conjugated structure.
  • the aromatic compound according to a preferred embodiment is one in which a group represented by the formula (1a) or the formula (1b) is bonded to the group represented by Ar 11 as X 11 or X 12 .
  • the group represented by the formula (1a) or the formula (1b) is included in the group represented by Ar 11 in addition to X 11 or X 12. May be.
  • the aromatic compound according to a preferred embodiment has a plurality of groups represented by the formula (1a) or the formula (1b), or groups represented by the formula (1a) and the formula (1b). In combination, this has high molecular planarity as a whole. Therefore, when used as an organic semiconductor material, the aromatic compound according to a preferred embodiment is a p-type semiconductor with good molecular packing and excellent charge transportability.
  • X 11 and X 12 may each independently be any of the groups represented by Formula (1a) and Formula (1b). Since the production of the aromatic compound according to the preferred embodiment can be facilitated and the packing of the molecule can be further improved, both X 11 and X 12 are groups represented by the formula (1a), or both are A group represented by the formula (1b) is more preferable. From this point of view, X 11 and X 12 are particularly preferably groups having the same structure.
  • Ar 12 and Ar 13 each independently represent an aromatic hydrocarbon group having 6 or more carbon atoms.
  • This aromatic hydrocarbon group may have groups represented by R 11 and R 13 .
  • the aromatic hydrocarbon group refers to a group composed of the remaining atomic group obtained by removing a hydrogen atom at a site used for bonding from an aromatic hydrocarbon ring.
  • the aromatic hydrocarbon group has preferably 6 to 60 carbon atoms, more preferably 6 to 20 carbon atoms.
  • the aromatic hydrocarbon ring includes a benzene ring and a condensed ring
  • examples of the condensed ring include a naphthalene ring, an anthracene ring, a tetracene ring, a pentacene ring, a pyrene ring, a perylene ring, and a fluorene ring.
  • the aromatic hydrocarbon group a group consisting of the remaining atomic group obtained by removing two hydrogen atoms from a benzene ring or naphthalene ring is preferable.
  • the aromatic hydrocarbon group may have one or more groups represented by R 11 and R 13 , but the carbon number of the aromatic hydrocarbon group described above includes the carbon number of the substituent. Suppose that it is not possible. Specific examples of the group represented by R 11 and R 13 will be described later.
  • a hydrogen atom, a halogen atom, a saturated or unsaturated hydrocarbon group, an aryl group, an alkoxy group, an alkylthio group, an arylalkyl group examples include an aryloxy group, a monovalent heterocyclic group, an amino group, a nitro group, and a cyano group.
  • R 11 , R 12 , R 13 and R 14 (referred to as “R 11 to R 14 ”, hereinafter, the same expressions are also expressed in the same manner) are each independently.
  • a halogen atom a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, for example.
  • Examples of the monovalent group include a group consisting of a linear or branched low molecular chain, a monovalent cyclic group having 3 to 60 carbon atoms (monocyclic, condensed ring, carbocyclic or heterocyclic ring, saturated Or may be unsaturated), saturated or unsaturated hydrocarbon group, hydroxyl group, alkoxy group, alkylthio group, alkanoyloxy group, amino group, oxyamino group, alkylamino group, dialkylamino group, alkanoylamino group, cyano group , A nitro group, a sulfo group, an alkyl group substituted with a halogen atom, an alkoxysulfonyl group, an alkylsulfonyl group, a sulfamoyl group, an alkylsulfamoyl group, a carboxyl group, a carbamoyl group, an alkylcarbamoyl group, an
  • R 11 to R 14 are each a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms. It is more preferably an alkylthio group, and further preferably a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. Further, since the solubility in an organic solvent is improved, it is preferable that at least one of R 11 and R 12 and at least one of R 13 and R 14 are an alkyl group having 6 to 12 carbon atoms. In particular, since the solubility in an organic solvent is enhanced while improving the stability of the aromatic compound, R 11 and R 13 are hydrogen atoms, and R 12 and R 14 are alkyl groups having 6 to 12 carbon atoms. It is preferable.
  • alkyl group examples include linear, branched or cyclic alkyl groups having 1 to 20 carbon atoms, and linear, branched or cyclic alkyl groups having 1 to 12 carbon atoms are preferable.
  • alkoxy group and the alkylthio group examples include an alkoxy group having 1 to 20 carbon atoms and an alkylthio group, and those having the above alkyl group in the structure can be exemplified.
  • alkoxy group and the alkylthio group those containing a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms are preferable.
  • X 13 to X 16 each independently represents an oxygen atom, a sulfur atom or a selenium atom.
  • at least one of X 13 and X 14 is a sulfur atom
  • at least one of X 15 and X 16 is a sulfur atom
  • all of X 13 to X 16 are sulfur. More preferably, it is an atom.
  • the Ar 11 is a group represented by the above formula (2) because a more excellent charge transport property tends to be obtained.
  • Ar 21 , Ar 22 and Ar 23 are each independently an aromatic hydrocarbon group having 6 or more carbon atoms which may have a substituent, or a substituent. It is a heterocyclic group having 4 or more carbon atoms which may be present.
  • aromatic hydrocarbon group include the same groups as the aromatic hydrocarbon groups exemplified as Ar 12 and Ar 13 described above.
  • the heterocyclic group refers to a group consisting of the remaining atomic group obtained by removing a hydrogen atom at a site used for bonding from a heterocyclic compound.
  • a heterocyclic compound is an organic compound having a cyclic structure, and the elements constituting the ring are not only carbon atoms, but also heteroatoms such as oxygen atoms, sulfur atoms, nitrogen atoms, phosphorus atoms, boron atoms, silicon atoms, etc. In the ring.
  • Ar 21 , Ar 22 or Ar 23 is a heterocyclic group, the corresponding group constitutes a corresponding heterocyclic ring.
  • the heterocyclic group an aromatic heterocyclic group is preferable.
  • the number of carbon atoms of the heterocyclic group is preferably 4 to 60, and more preferably 4 to 20.
  • the heterocyclic group may have one or more substituents. In that case, the carbon number of the heterocyclic group does not include the carbon number of the substituent.
  • Substituents include halogen atoms, saturated or unsaturated hydrocarbon groups, aryl groups, alkoxy groups, alkylthio groups, arylalkyl groups, aryloxy groups, monovalent heterocyclic groups, amino groups, nitro groups, and cyano groups. Can be mentioned.
  • Heterocyclic groups include thiophene rings, rings with 2-6 condensed thiophene rings (thienothiophene ring, dithienothiophene ring, etc.), rings with 2-6 thiophene rings and benzene rings (benzothiophene ring) , Benzodithiophene ring, benzothienothiophene ring, dibenzothienothiophene ring, etc.), cyclopentadithiophene ring, thiazole ring, pyrrole ring, pyridine ring, pyrimidine ring, pyrazine ring, remaining after removing two hydrogen atoms from triazine ring The group which consists of these atomic groups is illustrated.
  • a thiophene ring a group consisting of the remaining atomic groups obtained by removing 2 hydrogen atoms from a ring condensed with 2 to 6 thiophene rings (thienothiophene ring, dithienothiophene ring), thiophene ring and benzene ring are 2
  • a group consisting of the remaining atomic groups obtained by removing 2 hydrogen atoms from a ring condensed with 6 to 6 rings is preferred.
  • a group composed of the remaining atomic group obtained by removing two hydrogen atoms from a thiophene ring or thienothiophene ring is preferable.
  • These suitable heterocyclic groups exhibit characteristic electrical properties such that they can emit electrons at a desired potential to assume a stable radical cation state.
  • Aromatic compounds are expected to have high charge transport properties as organic p-type semiconductors. Therefore, in order to enhance this effect, the planarity of the ⁇ -conjugated structure of the group represented by Ar 11 , particularly the group represented by the formula (2), is enhanced, and a ⁇ - ⁇ stack structure is easily obtained. It is preferable. From such a viewpoint, Ar 21 , Ar 22 and Ar 23 are preferably a structure containing a condensed ring or a thiophene ring. In particular, a structure including a thiophene ring is more preferable because the plane spacing of the ⁇ - ⁇ stack structure can be reduced.
  • At least one of Ar 21 , Ar 22 and Ar 23 is preferably a thiophenediyl group which may have a substituent or a thienothiophenediyl group which may have a substituent, and Ar 21 , Ar It is particularly preferable that all of 22 and Ar 23 are a thiophenediyl group which may have a substituent or a thienothiophenediyl group which may have a substituent.
  • Ar ⁇ 21 >, Ar ⁇ 22 > and Ar ⁇ 23 > has a substituent.
  • this substituent an alkyl group is preferable, and an alkyl group having 6 to 12 carbon atoms is more preferable.
  • n, n and p are each independently an integer of 0 to 6
  • m + n + p is an integer of 1 to 10.
  • m + n + p is more preferably an integer of 1 to 3 because high charge transportability and stability can be obtained and the production of the aromatic compound can be facilitated.
  • X 11 and X 12 are groups represented by the formula (1a)
  • Ar 11 is a group represented by the formula (2)
  • a compound in which Ar 12 is a phenyl group and X 13 and X 14 are sulfur atoms is preferable because the effects of the present invention can be obtained particularly well.
  • Such an aromatic compound is represented by Formula (3).
  • R 11 , R 12 , Ar 21 , Ar 22 , Ar 23 , m, n and p are all as defined above, and a plurality of groups having the same sign present in the molecule are Each may be the same or different.
  • Examples of the aromatic compound represented by the formula (1) include compounds represented by the following formulas (11) to (24).
  • m ′ and n ′ each independently represent an integer of 1 to 20, and preferably an integer of 6 to 12.
  • the aromatic compound represented by the formula (1) is, for example, a raw material compound for forming a group represented by X 11 and X 12, that is, a group represented by the formula (1a) and / or the formula (1b). And a raw material compound for forming a group represented by Ar 11 can be prepared, and then reacted.
  • a method for forming a group represented by the typical formula (1a) will be described as an example of X 11 and X 12 .
  • a compound represented by the following formula (30) As a raw material compound for forming a group represented by the formula (1a), a compound represented by the following formula (30), and as a raw material compound for forming a group represented by Ar 11 , Examples thereof include compounds represented by the following formula (31).
  • R 11 , R 12 , Ar 11 , Ar 12 , X 13 and X 14 are all as defined above.
  • W 0 , W 1 and W 2 are hydrogen atom, halogen atom, alkylsulfonate group, arylsulfonate group, arylalkylsulfonate group, alkylstannyl group, arylstannyl group, arylalkylstannyl group, boric acid ester residue Group, sulfonium methyl group, phosphonium methyl group, phosphonate methyl group, monohalogenated methyl group, boric acid residue (—B (OH) 2 ), formyl group and vinyl group.
  • a halogen atom, an alkylstannyl group, and a borate ester residue are preferable.
  • the boric acid ester residue include a group represented by the following formula.
  • W 1 and W 2 are each independently a halogen atom, an alkyl sulfonate group, an aryl sulfonate group, An arylalkyl sulfonate group, a boric acid ester residue, a boric acid residue or a trialkylstannyl group is preferred.
  • the raw material compound represented by Formula (30) can be synthesized, for example, according to the procedure represented by the following reaction scheme.
  • R 11 , R 12 , Ar 12 , X 13 , X 14 and W 0 are as defined above, and X 31 and X 32 are each independently Represents a halogen atom.
  • Examples of the method for producing an aromatic compound using the raw material compound described above include, for example, a method using a Suzuki coupling reaction, a method using a Grignard reaction, a method using a Stille reaction, a method using a Ni (0) catalyst, A method using an oxidant such as FeCl 3, a method using an anion oxidation reaction, a method using palladium acetate and an organic base, a method of oxidative coupling by preparing an ⁇ -unsubstituted or halogenated lithio isomer, and electrochemical Examples thereof include a method using an oxidation reaction and a method by decomposing an intermediate compound having an appropriate leaving group. These can be selected according to the structure of the raw material compound and the target aromatic compound.
  • a method using a Suzuki coupling reaction a method using a Grignard reaction, a method using a Stille reaction, a method using a Ni (0) catalyst, a method using an anion oxidation reaction, a method using palladium acetate and an organic base
  • a method using a Suzuki coupling reaction a method using a Grignard reaction, a method using a Stille reaction, a method using a Ni (0) catalyst, a method using an anion oxidation reaction, a method using palladium acetate and an organic base
  • an inorganic base such as potassium carbonate, sodium carbonate, or barium hydroxide, an organic base such as triethylamine, or a fluoride.
  • An inorganic salt such as cesium is added in an amount equal to or greater than the monomer, preferably 1 to 10 equivalents, and the raw material compound is reacted.
  • Examples of the solvent used in this reaction include N, N-dimethylformamide, toluene, dimethoxyethane, and tetrahydrofuran.
  • the reaction temperature depends on the solvent used, but is preferably 50 to 160 ° C. In the reaction, the temperature may be raised to near the boiling point of the solvent and refluxed.
  • the preferred reaction time is 1 to 200 hours.
  • Suzuki coupling reaction can be performed in accordance with, for example, the method described in Chemical Review (Chem. Rev.), Vol. 95, p. 2457 (1995).
  • Ni (0) catalyst in addition to a method using a zero-valent nickel complex as a Ni (0) catalyst, a method in which a nickel salt is reacted in the presence of a reducing agent to generate zero-valent nickel in the system.
  • the zerovalent nickel complex include bis (1,5-cyclooctadiene) nickel (0), (ethylene) bis (triphenylphosphine) nickel (0), and tetrakis (triphenylphosphine) nickel. Of these, bis (1,5-cyclooctadiene) nickel (0) is preferred because of its high versatility and low cost.
  • the neutral ligand is a ligand having no anion or cation.
  • nitrogen-containing ligands such as 2,2′-bipyridyl, 1,10-phenanthroline, methylenebisoxazoline, N, N′-tetramethylethylenediamine; triphenylphosphine, tolylphosphine, tributylphosphine, triphenoxyphosphine, etc.
  • nitrogen-containing ligands are preferred because they are versatile and inexpensive.
  • 2,2'-bipyridyl is preferable because high reactivity can be obtained and a high yield can be achieved. More specifically, since the yield of the aromatic compound is improved, 2,2′-bipyridyl is added as a neutral ligand to a system containing bis (1,5-cyclooctadiene) nickel (0). It is preferable to carry out the reaction.
  • nickel chloride or nickel acetate can be used as the nickel salt.
  • the reducing agent include zinc, sodium hydride, hydrazine and derivatives thereof, and lithium aluminum hydride.
  • reaction for example, palladium [tetrakis (triphenylphosphine)] or palladium acetate is used as a catalyst, and the reaction is performed using an organic tin compound as a monomer.
  • the solvent used in this reaction include N, N-dimethylformamide, toluene, dimethoxyethane, and tetrahydrofuran.
  • the reaction temperature depends on the solvent used, but is preferably 50 to 160 ° C. Further, the temperature may be raised to near the boiling point of the solvent and refluxed.
  • the reaction time is preferably 1 to 200 hours.
  • a halogen-substituted product or hydrogen-substituted product such as a raw material compound is used as a monomer and reacted with n-butyllithium to prepare a lithiated compound, which is obtained by using copper (II) bromide, Treat with an oxidizing agent such as copper (II) chloride or iron (III) acetylacetonate.
  • the solvent used in this reaction include toluene, dimethoxyethane, tetrahydrofuran, hexane, heptane, and octane.
  • the reaction temperature depends on the solvent used, but is preferably 50 to 160 ° C. Further, the temperature may be raised to near the boiling point of the solvent and refluxed.
  • the reaction time is preferably 5 minutes to 200 hours.
  • a halogen-substituted product is used as a monomer, and the reaction is carried out by adding palladium (II) acetate and an organic base such as diisopropylamine or triethylamine.
  • the solvent used in this reaction include N, N-dimethylformamide, toluene, dimethoxyethane, and tetrahydrofuran.
  • the reaction temperature depends on the solvent used, but is preferably 50 to 160 ° C. Further, the temperature may be raised to near the boiling point of the solvent and refluxed.
  • the reaction time is preferably 5 minutes to 200 hours.
  • Organic thin film Next, an organic thin film according to a preferred embodiment will be described.
  • the organic thin film according to a preferred embodiment contains the above-described aromatic compound.
  • the organic thin film may contain one kind of aromatic compound independently, and may contain two or more kinds of aromatic compounds.
  • the organic thin film in order to increase the electron transport property or hole transport property, has a low molecular compound having electron transport property or hole transport property other than the aromatic compound, or an electron transport property different from the aromatic compound or A polymer compound having a hole transport property (these low molecular compounds and polymer compounds are collectively referred to as “electron transport material” and “hole transport material”) may be included.
  • Examples of the hole transport material include pyrazoline, arylamine, stilbene, triaryldiamine, oligothiophene, polyvinylcarbazole, polysilane, polysiloxane having an aromatic amine in the side chain or main chain, polyaniline, polythiophene, polypyrrole, polyarylene.
  • Examples include vinylene, polythienylene vinylene, and derivatives thereof.
  • Examples of the electron transporting material include oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, diphenoquinone, 8-hydroxyquinoline metal complex, polyquinoline, polyquinoline, quinoxaline, polyfluorenes, fullerenes such as C 60, and derivatives thereof.
  • the organic thin film of this embodiment may include a charge generation material in order to generate a charge by light absorbed in the organic thin film.
  • a charge generation material for example, azo compounds, diazo compounds, metal-free phthalocyanine compounds, metal phthalocyanine compounds, perylene compounds, polycyclic quinone compounds, squarylium compounds, azulenium compounds, fullerenes such thiapyrylium compounds and C 60 and the like .
  • the organic thin film may further contain materials necessary for developing various functions.
  • materials include, for example, a sensitizer for sensitizing the function of generating charge by absorbed light, a stabilizer for increasing stability, and UV absorption for absorbing ultraviolet (UV) light. Agents.
  • the organic thin film may contain a polymer compound material other than the compounds exemplified as the above-described components as a polymer binder in order to improve mechanical properties.
  • a polymer binder those that do not extremely inhibit the electron transport property or hole transport property are preferable, and those that do not strongly absorb visible light are preferable.
  • polymer binder examples include poly (N-vinylcarbazole), polyaniline, polythiophene, poly (p-phenylene vinylene), poly (2,5-thienylene vinylene), polycarbonate, polyacrylate, polymethyl acrylate, and polymethyl.
  • examples include methacrylate, polystyrene, polyvinyl chloride, polysiloxane, and derivatives thereof.
  • Examples of the method for producing the organic thin film of the present embodiment include, for example, an aromatic compound, an electron transporting material, a hole transporting material, a solution containing a polymer binder and a solvent to be mixed as necessary (that is, a composition).
  • the method by the film-forming using is mentioned.
  • an organic thin film can also be formed by a vacuum evaporation method.
  • the purity affects the device characteristics. Therefore, even if purification is performed by a method such as sublimation purification or recrystallization before the production of the organic thin film. Good.
  • the solvent used in the solution may be any solvent that can dissolve the aromatic compound, the electron transporting material or hole transporting material to be mixed, and the polymer binder.
  • unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexyl, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, Halogenated saturated hydrocarbon solvents such as bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, and trichlorobenz
  • Film formation methods include spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing.
  • Application methods such as offset printing, ink jet printing, dispenser printing, nozzle coating and capillary coating can be used. Of these, spin coating, flexographic printing, ink jet printing, dispenser printing, nozzle coating, and capillary coating are preferred.
  • the thickness of the organic thin film is preferably 1 nm to 100 ⁇ m, more preferably 2 nm to 1000 nm, still more preferably 5 nm to 500 nm, and particularly preferably 20 nm to 200 nm.
  • the step of manufacturing the organic thin film may include a step of orienting the aromatic compound.
  • a method for aligning the aromatic compound a method known as a liquid crystal alignment method can be used.
  • the rubbing method, the photo-alignment method, the sharing method (shear stress application method) and the pulling coating method tend to be simple and useful as the alignment method and easy to use.
  • the rubbing method and the sharing method are preferable.
  • the organic thin film Since the organic thin film has a charge transporting property, it can control the transport of charges injected from the electrodes and the charges generated by light absorption.
  • the organic thin film transistor, the organic photoelectric conversion element (organic solar cell, It can be used for organic thin film elements such as optical sensors. When an organic thin film is used for these organic thin film elements, the charge transporting property tends to be further improved if the aromatic compound is aligned by the alignment treatment.
  • organic thin film element Next, an organic thin film element according to a preferred embodiment will be described.
  • the organic thin film element to which the organic thin film containing the aromatic compound described above is applied include an organic thin film transistor and an organic photoelectric conversion element.
  • a solar cell and an optical sensor which are examples of the organic thin film transistor and the organic photoelectric conversion element will be described.
  • an organic thin film transistor includes, for example, a source electrode and a drain electrode, an active layer (organic thin film layer) made of an organic thin film containing an aromatic compound as a current path between them, and a gate electrode for controlling the amount of current passing through the current path. It has the structure provided. Examples of such an organic thin film transistor include a field effect type and an electrostatic induction type.
  • a field-effect organic thin film transistor includes a source electrode and a drain electrode, an active layer containing an aromatic compound as a current path between them, a gate electrode for controlling the amount of current passing through the current path, and between the active layer and the gate electrode. It is preferable to provide an insulating layer disposed on the surface.
  • the source electrode and the drain electrode are preferably provided in contact with the active layer containing an aromatic compound
  • the gate electrode is preferably provided with an insulating layer in contact with the active layer interposed therebetween.
  • the electrostatic induction type organic thin film transistor has a source electrode and a drain electrode, an active layer that becomes a current path between them and contains an aromatic compound, and a gate electrode that controls an amount of current passing through the current path.
  • the source electrode, the drain electrode, and the gate electrode provided in the active layer are preferably provided in contact with the active layer containing the aromatic compound.
  • the structure of the gate electrode may be any structure as long as a current path flowing from the source electrode to the drain electrode is formed and the amount of current flowing through the current path can be controlled by a voltage applied to the gate electrode. It is done.
  • FIG. 1 is a schematic cross-sectional view of an organic thin film transistor (field effect organic thin film transistor) according to a first embodiment.
  • An organic thin film transistor 100 shown in FIG. 1 includes a substrate 1, a source electrode 5 and a drain electrode 6 formed on the substrate 1 with a predetermined interval, and a source electrode 5 and a drain electrode 6 so as to cover the substrate 1. Formed on the insulating layer 3 so as to cover the region of the insulating layer 3 between the source electrode 5 and the drain electrode 6, the insulating layer 3 formed on the active layer 2, and the insulating layer 3 formed between the source electrode 5 and the drain electrode 6. And a gate electrode 4.
  • FIG. 2 is a schematic cross-sectional view of an organic thin film transistor (field effect organic thin film transistor) according to a second embodiment.
  • An organic thin film transistor 110 shown in FIG. 2 includes a substrate 1, a source electrode 5 formed on the substrate 1, an active layer 2 formed on the substrate 1 so as to cover the source electrode 5, a source electrode 5 and a predetermined electrode.
  • the drain electrode 6 formed on the active layer 2 with an interval of the insulating layer 3 formed on the active layer 2 and the drain electrode 6, and the insulating layer 3 between the source electrode 5 and the drain electrode 6.
  • a gate electrode 4 formed on the insulating layer 3 so as to cover the region.
  • FIG. 3 is a schematic cross-sectional view of an organic thin film transistor (field effect organic thin film transistor) according to a third embodiment.
  • the organic thin film transistor 120 shown in FIG. 3 includes a substrate 1, an active layer 2 formed on the substrate 1, a source electrode 5 and a drain electrode 6 formed on the active layer 2 with a predetermined interval, and a source electrode. 5 and the drain electrode 6 so as to partially cover the insulating layer 3 formed on the active layer 2, the region of the insulating layer 3 where the source electrode 5 is formed below, and the drain electrode 6 are formed below.
  • a gate electrode 4 formed on the insulating layer 3 so as to partially cover the region of the insulating layer 3.
  • FIG. 4 is a schematic cross-sectional view of an organic thin film transistor (field effect organic thin film transistor) according to a fourth embodiment.
  • 4 includes a substrate 1, a gate electrode 4 formed on the substrate 1, an insulating layer 3 formed on the substrate 1 so as to cover the gate electrode 4, and the gate electrode 4 at the bottom.
  • the source electrode 5 and the drain electrode 6 formed on the insulating layer 3 at a predetermined interval so as to partially cover the region of the insulating layer 3 formed on the substrate, and the source electrode 5 and the drain electrode 6 are partially covered.
  • the active layer 2 formed on the insulating layer 3 is provided.
  • FIG. 5 is a schematic cross-sectional view of an organic thin film transistor (field effect organic thin film transistor) according to a fifth embodiment.
  • An organic thin film transistor 140 shown in FIG. 5 includes a substrate 1, a gate electrode 4 formed on the substrate 1, an insulating layer 3 formed on the substrate 1 so as to cover the gate electrode 4, and the gate electrode 4 at the bottom.
  • a source electrode 5 formed on the insulating layer 3 so as to partially cover the region of the insulating layer 3 formed on the active layer 2 and an active layer 2 formed on the insulating layer 3 so as to partially cover the source electrode 5.
  • a drain electrode 6 formed on the insulating layer 3 at a predetermined interval so as to partially cover the region of the active layer 2 formed below the gate electrode 4 It is.
  • FIG. 6 is a schematic cross-sectional view of an organic thin film transistor (field effect organic thin film transistor) according to a sixth embodiment.
  • An organic thin film transistor 150 shown in FIG. 6 includes a substrate 1, a gate electrode 4 formed on the substrate 1, an insulating layer 3 formed on the substrate 1 so as to cover the gate electrode 4, and the gate electrode 4 at the bottom.
  • the active layer 2 is formed on the insulating layer 3 so as to partially cover the region of the active layer 2 formed under the active layer 2 and the gate electrode 4 formed below.
  • the source electrode 5 and the drain electrode 6 formed on the insulating layer 3 with a predetermined distance from the source electrode 5 so as to partially cover the region of the active layer 2 where the gate electrode 4 is formed below. , Are provided.
  • FIG. 7 is a schematic cross-sectional view of an organic thin film transistor (static induction organic thin film transistor) according to a seventh embodiment.
  • the organic thin film transistor 160 shown in FIG. 7 includes a substrate 1, a source electrode 5 formed on the substrate 1, an active layer 2 formed on the source electrode 5, and a plurality on the active layer 2 with a predetermined interval.
  • a drain electrode 6 formed on the active layer 2a.
  • the active layer 2 and / or the active layer 2a contains the aromatic compound of the present invention, and the current path between the source electrode 5 and the drain electrode 6 ( Channel).
  • the gate electrode 4 controls the amount of current passing through the current path (channel) in the active layer 2 and / or the active layer 2a by applying a voltage.
  • the field effect organic thin film transistor of the above-described form can be manufactured by a known method, for example, a method described in JP-A-5-110069.
  • the electrostatic induction organic thin film transistor can be produced by a known method, for example, a method described in JP-A-2004-006476.
  • a glass substrate, a flexible film substrate, and a plastic substrate can be used as long as the characteristics as an organic thin film transistor are not impaired.
  • the aromatic compound is soluble in an organic solvent.
  • the organic thin film used as the active layer 2 can be formed by applying the manufacturing method of the organic thin film by application
  • any material having high electrical insulation may be used, and a known material can be used.
  • a known material can be used.
  • the surface of the insulating layer 3 is treated with a surface treatment agent such as a silane coupling agent. It is also possible to form the active layer 2 after surface modification.
  • a surface treatment agent such as a silane coupling agent.
  • the surface treatment agent include silylamine compounds such as long-chain alkylchlorosilanes, long-chain alkylalkoxysilanes, fluorinated alkylchlorosilanes, fluorinated alkylalkoxysilanes, and hexamethyldisilazane.
  • the surface of the insulating layer 3 can be treated with ozone UV or O 2 plasma.
  • an organic thin-film transistor after manufacturing the organic thin film transistor, it is preferable to form a protective film on the organic thin film transistor in order to protect the element.
  • an organic thin-film transistor can be interrupted
  • the influence on the organic thin-film transistor by the manufacturing process of a display device can be reduced with a protective film.
  • Examples of the method for forming the protective film include a method of covering the organic thin film transistor with a UV curable resin, a thermosetting resin, or an inorganic SiONx film.
  • a UV curable resin for example, a UV curable resin, a thermosetting resin, or an inorganic SiONx film.
  • the steps from the preparation of the organic thin film transistor to the formation of the protective film are performed without exposure to the atmosphere (for example, in a dry nitrogen atmosphere or in a vacuum). Is preferred.
  • organic photoelectric conversion element Typical examples of the organic photoelectric conversion element include a solar cell and an optical sensor as described above.
  • FIG. 8 is a schematic cross-sectional view showing a solar cell according to a preferred embodiment.
  • the solar cell 200 shown in FIG. 8 includes an active layer 2 made of a substrate 1, a first electrode 7a formed on the substrate 1, and an organic thin film containing an aromatic compound formed on the first electrode 7a. And a second electrode 7 b formed on the active layer 2.
  • a transparent or translucent electrode is used for one of the first electrode 7a and the second electrode 7b.
  • an electrode material metals such as aluminum, gold, silver, copper, alkali metal, alkaline earth metal, and semi-transparent films and transparent conductive films thereof can be used.
  • the electrode material is preferably selected so that the work function difference between the first electrode 7a and the second electrode 7b is large in order to obtain a high open circuit voltage.
  • a charge generating agent, a sensitizer, or the like may be added to the active layer 2 in order to increase photosensitivity.
  • the substrate 1 a silicon substrate, a glass substrate, a plastic substrate, or the like can be used.
  • FIG. 9 is a schematic cross-sectional view showing the photosensor according to the first embodiment.
  • An optical sensor 300 shown in FIG. 9 includes an active layer 2 made of a substrate 1, a first electrode 7a formed on the substrate 1, and an organic thin film containing an aromatic compound formed on the first electrode 7a. And a charge generation layer 8 formed on the active layer 2 and a second electrode 7b formed on the charge generation layer 8.
  • FIG. 10 is a schematic cross-sectional view of an optical sensor according to the second embodiment.
  • An optical sensor 310 illustrated in FIG. 10 is formed on the substrate 1, the first electrode 7a formed on the substrate 1, the charge generation layer 8 formed on the first electrode 7a, and the charge generation layer 8.
  • FIG. 11 is a schematic cross-sectional view of an optical sensor according to the third embodiment.
  • An optical sensor 320 shown in FIG. 11 includes an active layer 2 made of an organic thin film containing a substrate 1, a first electrode 7a formed on the substrate 1, and an aromatic compound formed on the first electrode 7a. And a second electrode 7 b formed on the active layer 2.
  • a transparent or translucent electrode is used as one of the first electrode 7a and the second electrode 7b.
  • an electrode material metals such as aluminum, gold, silver, copper, alkali metal, alkaline earth metal, and their translucent films and transparent conductive films can be used.
  • the charge generation layer 8 is a layer that absorbs light and generates charges.
  • a carrier generating agent, a sensitizer, or the like may be added to the active layer 2 in order to increase photosensitivity.
  • the base material 1 a silicon substrate, a glass substrate, a plastic substrate, etc. can be used as the base material 1.
  • Cyclic voltammetry uses the product name “CV-50W” manufactured by BAS Co., Ltd. (BAS) as a measuring device, a Pt electrode manufactured by BAS as a working electrode, a Pt wire as a counter electrode, and a reference electrode It measured using the Ag line. During this measurement, the sweep speed was 100 mV / second, and the scanning potential region was 0 to 1.2V. The oxidation potential was measured by completely dissolving 3 ⁇ 10 ⁇ 3 mol / L of the compound and 0.1 mol / L of tetrabutylammonium hexafluorophosphate (TBAPF6) as a supporting electrolyte in a dichloromethane solvent.
  • BAS BAS Co., Ltd.
  • the oxidation potential (E 1/2 ox) was determined as the rising potential of the oxidation wave.
  • the HOMO (maximum occupied molecular orbital) level was determined from the first oxidation potential with ferrocene as an internal standard (oxidation potential -0.21 V, 4.8 eV from the vacuum level).
  • the ultraviolet (UV) absorption spectrum was measured by using a trade name “UV-2500PC” manufactured by Shimadzu Corporation as a measuring apparatus and dissolving the compound in chloroform at a concentration of 5 ⁇ 10 ⁇ 6 M.
  • the energy band gap was determined from the UV absorption edge wavelength.
  • Tridecan-1-one (Compound B represented by the following formula (B) was obtained in the form of a yellowish white solid (213 mg, yield 49%).
  • Synthesis Example 3 Synthesis of ethyl 3-dodecylbenzo [4,5] thieno [3,2-b] -2-thiophenecarboxylate
  • 213 mg (0.58 mmol) of the compound B obtained above 77.0 mg (0.64 mmol) of ethyl thioglycolate, 160 mg (1.16 mmol) of potassium carbonate, N, N-dimethyl 3 mL of formamide (DMF) was added respectively, and these were stirred at room temperature for 18 hours. Thereafter, an ethanol solution of sodium hydroxide (0.5 M, 0.4 mL) was added, and the mixture was further stirred for 2 hours.
  • sodium hydroxide 0.5 M, 0.4 mL
  • reaction solution after this reaction was extracted with ether and dried over sodium sulfate, and then the solvent was distilled off. Thereafter, the obtained reaction solution is purified by silica gel column chromatography using hexane containing 0.5% by weight of ethyl acetate as a developing solvent, whereby the desired 3-dodecylbenzo [4,5] thieno [3, 2-b] -ethyl 2-thiophenecarboxylate (compound C represented by the following formula (C)) was obtained in the form of a yellow solid (224 mg, yield 90%).
  • Synthesis Example 4 Synthesis of 3-dodecylbenzo [4,5] thieno [3,2-b] -2-thiophenecarboxylic acid To a 100 mL eggplant flask, 294 mg (0.68 mmol) of Compound C obtained above, 114 mg (2.04 mmol) of potassium hydroxide, 1 mL of water and 5 mL of ethanol were added, and the mixture was stirred at 100 ° C. for 8 hours. did.
  • the energy band gap obtained from the UV absorption spectrum of Compound G was 2.6 eV. Further, the first / second oxidation potential obtained by cyclic voltammetry was 0.59 / 0.89V, and the HOMO level obtained from the first oxidation potential was 5.18 eV. The ionization potential determined by AC-2 was 5.4 eV.
  • the energy band gap obtained from the UV absorption spectrum of Compound H was 2.7 eV.
  • the first / second oxidation potential obtained by cyclic voltammetry was 0.67 / 1.07V, and the HOMO level obtained from the first oxidation potential was 5.26 eV.
  • the ionization potential obtained by AC-2 was 5.6 eV.
  • 3-Chlorobenzo [b] thiophene (260 mg, 1.54 mmol) was placed in a 20 mL three-necked flask and dissolved in THF (5 mL). Next, the gas in the three-necked flask was replaced with nitrogen and cooled to -78 ° C. Subsequently, n-butyllithium (1.57 M hexane solution, 1.1 mL, 1.7 mmol) was added and stirred for 1 hour. Thereafter, decanal (266 mg, 1.7 mmol) was added and the mixture was returned to room temperature, and further stirred for 3 hours.
  • the ionization potential of Compound N determined by AC-2 was 5.3 eV.
  • the ionization potential of Compound O determined by AC-2 was 5.3 eV.
  • Example 5 (Preparation of organic thin film transistor 1 and evaluation of transistor characteristics) A substrate was prepared in which a silicon oxide film serving as an insulating layer was formed by thermal oxidation on the surface of a heavily doped p-type silicon substrate serving as a gate electrode. This substrate was set on a spin coater, and a ⁇ -phenethyltrichlorosilane / toluene (100 ⁇ L / 10 mL) solution was dropped and spun to modify the surface of the silicon oxide film.
  • the obtained organic thin film transistor 1 was applied with a gate voltage Vg of 0 to ⁇ 60 V and a source-drain voltage Vsd of 0 to ⁇ 60 V in a vacuum, and when the transistor characteristics were measured, a good drain current-gate voltage (Id ⁇ Vg) characteristics were obtained.
  • the mobility at this time was 6.8 ⁇ 10 ⁇ 3 cm 2 / Vs
  • the threshold voltage was ⁇ 16 V
  • the on / off ratio was 7 ⁇ 10 4 . From this, it was confirmed that the organic thin film transistor 1 using the compound G functions effectively as a p-type organic transistor. Further, the organic thin film transistor 1 operated stably even when it was repeatedly measured.
  • Example 6 Manufacture of organic thin film transistor 2 and evaluation of transistor characteristics
  • An organic thin film transistor 2 was produced in the same manner as in Example 5 except that the compound N synthesized in Example 3 was used in place of the compound G synthesized in Example 1.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Junction Field-Effect Transistors (AREA)
  • Photovoltaic Devices (AREA)
  • Light Receiving Elements (AREA)

Abstract

La présente invention concerne un composé aromatique qui fait preuve d'excellentes propriétés de transport de charges, et qui convient comme substance semi-conductrice organique dotée d'une haute stabilité. Ce composé aromatique est représenté par la formule (1). Dans cette formule, Ar11 est un groupe contenant un noyau aromatique, et X11 et X12 sont des groupes représentés par les formules (1a) et (1b). Dans les formules (1a) et (1b), Ar12 et Ar13 sont chacun un groupe hydrocarbure aromatique portant au moins 6 atomes de carbone, R11, R12, R13, et R14 sont chacun un atome d'hydrogène, un atome halogène, ou un groupe monovalent, et enfin, X13, X14, X15, et X16 sont chacun un atome d'oxygène, un atome de soufre, ou un atome de sélénium.
PCT/JP2011/053287 2010-02-18 2011-02-16 Composé aromatique, film mince organique l'utilisant, et élément de film mince organique pourvu de ce film mince organique WO2011102390A1 (fr)

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