WO2011138935A1 - Élément organique de conversion photoélectrique - Google Patents

Élément organique de conversion photoélectrique Download PDF

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WO2011138935A1
WO2011138935A1 PCT/JP2011/060494 JP2011060494W WO2011138935A1 WO 2011138935 A1 WO2011138935 A1 WO 2011138935A1 JP 2011060494 W JP2011060494 W JP 2011060494W WO 2011138935 A1 WO2011138935 A1 WO 2011138935A1
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group
compound
photoelectric conversion
condensed
organic photoelectric
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上谷　保則
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住友化学株式会社
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • H—ELECTRICITY
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
    • H—ELECTRICITY
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/50—Photovoltaic [PV] devices
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/115—Polyfluorene; Derivatives thereof
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/151—Copolymers
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
    • H10K85/211—Fullerenes, e.g. C60
    • H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
    • 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 present invention relates to an organic photoelectric conversion element.
  • an organic photoelectric conversion element such as an organic solar cell or an optical sensor
  • an organic photoelectric conversion element including a composition containing various polymer compounds has been studied.
  • an organic solar cell having an organic layer containing poly-3-hexylthiophene as a conjugated polymer compound and C60PCBM as a fullerene derivative is described (Advanced Functional Materials, Vol. 13, p.85, 2003).
  • the organic photoelectric conversion element has a problem that an open circuit voltage (Voc) is not always sufficient.
  • the present invention provides an organic photoelectric conversion element that can provide a high open-circuit voltage. That is, the present invention has a pair of electrodes and an organic layer provided between the electrodes, and the organic layer comprises a compound having a condensed ring in which 4 to 10 benzene rings are condensed and a conjugated polymer compound. An organic photoelectric conversion element is provided.
  • the organic photoelectric conversion device of the present invention has an organic layer containing a compound having a condensed ring in which 4 to 10 benzene rings are condensed, preferably a condensed ring in which 4 to 7 benzene rings are condensed, and a conjugated polymer compound.
  • the compound having a condensed ring in which 4 to 10 benzene rings are condensed means a compound having, as a partial structure, a condensed polycyclic hydrocarbon in which 4 to 10 optionally substituted benzene rings are condensed, Examples thereof include compounds having a pyrene ring, a tetracene ring, a chrysene ring, a triphenylene ring, a perylene ring, a pentacene ring, and a picene ring.
  • the substituents that these compounds may have include a halogen atom, an alkyl group that may be substituted with fluorine, an alkoxy group that may be substituted with fluorine, an alkylthio group that may be substituted with fluorine, and a substituted group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the alkyl group usually has 1 to 20 carbon atoms, and may be linear, branched or cyclic. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, sec-butyl group, 3-methylbutyl group, pentyl group, hexyl group and 2-ethylhexyl.
  • alkyl group in which a hydrogen atom is substituted with a fluorine atom examples include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, and a perfluorooctyl group.
  • the alkoxy group usually has 1 to 20 carbon atoms, and the alkyl portion thereof may be linear or branched, or may be cyclic.
  • alkoxy group examples include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyl
  • examples thereof include an oxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, and a lauryloxy group.
  • Examples of the alkoxy group in which a hydrogen atom is substituted with a fluorine atom include a trifluoromethoxy group, a pentafluoroethoxy group, a perfluorobutoxy group, a perfluorohexyloxy group, and a perfluorooctyloxy group.
  • the alkylthio group usually has 1 to 20 carbon atoms, and the alkyl portion may be linear or branched or may be cyclic.
  • alkylthio group examples include methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, sec-butylthio group, tert-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group.
  • Examples of the alkylthio group in which a hydrogen atom is substituted with a fluorine atom include a trifluoromethylthio group.
  • An aryl group is an atomic group obtained by removing one hydrogen atom on an aromatic ring from an aromatic hydrocarbon, having a benzene ring, a condensed ring, an independent benzene ring or two or more condensed rings directly Or the thing couple
  • the aryl group usually has 6 to 60 carbon atoms, preferably 6 to 48 carbon atoms.
  • the aryl group may have a substituent.
  • substituents examples include a linear or branched alkyl group having 1 to 20 carbon atoms or an alkoxy group having a cycloalkyl group having 3 to 20 carbon atoms in the structure thereof, formula (1): (In the formula, g represents an integer of 1 to 6, and h represents an integer of 0 to 5.) And a group represented by formula (I) and a fluorine atom.
  • aryl group which may be substituted include a phenyl group and a C 1 to C 12 alkoxyphenyl group (C 1 to C 12 represents 1 to 12 carbon atoms. The same applies hereinafter.
  • C 1 ⁇ C 12 alkylphenyl group 1-naphthyl, 2-naphthyl, 1-anthracenyl group, 9-anthracenyl group and a pentafluorophenyl group and the like
  • C 1 ⁇ C 12 alkoxy A phenyl group and a C 1 -C 12 alkylphenyl group are preferred.
  • C 1 to C 12 alkoxyphenyl group examples include a methoxyphenyl group, an ethoxyphenyl group, a propoxyphenyl group, an isopropoxyphenyl group, a butoxyphenyl group, an isobutoxyphenyl group, a sec-butoxyphenyl group, and a tert-butoxyphenyl group.
  • C 1 ⁇ C 12 alkyl phenyl group methylphenyl group, ethylphenyl group, dimethylphenyl group, propylphenyl group, mesityl group, methylethylphenyl group, isopropylphenyl group, butylphenyl group, isobutylphenyl group
  • Examples include sec-butylphenyl group, tert-butylphenyl group, pentylphenyl group, isoamylphenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonylphenyl group, decylphenyl group and dodecylphenyl group.
  • the aryloxy group usually has 6 to 60 carbon atoms, preferably 6 to 48 carbon atoms.
  • the aryloxy group may have a substituent. Specific examples of the substituent are the same as those described above as the substituent of the aryl group.
  • Specific examples of the optionally substituted aryloxy group include a phenoxy group, a C 1 to C 12 alkoxyphenoxy group, a C 1 to C 12 alkylphenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, and pentafluoro phenoxy group and the like, C 1 ⁇ C 12 alkoxyphenoxy groups and C 1 ⁇ C 12 alkylphenoxy group are preferable.
  • C 1 -C 12 alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2- Examples include ethylhexyloxy, nonyloxy, decyloxy, 3,7-dimethyloctyloxy and lauryloxy.
  • C 1 to C 12 alkylphenoxy group examples include methylphenoxy group, ethylphenoxy group, dimethylphenoxy group, propylphenoxy group, 1,3,5-trimethylphenoxy group, methylethylphenoxy group, isopropylphenoxy group, butyl Phenoxy group, isobutylphenoxy group, sec-butylphenoxy group, tert-butylphenoxy group, pentylphenoxy group, isoamylphenoxy group, hexylphenoxy group, heptylphenoxy group, octylphenoxy group, nonylphenoxy group, decylphenoxy group and dodecylphenoxy group Is mentioned.
  • the arylthio group usually has 6 to 60 carbon atoms.
  • the arylthio group may have a substituent. Specific examples of the substituent are the same as those described above as the substituent of the aryl group. Specific examples of the optionally substituted arylthio group, phenylthio group, C 1 ⁇ C 12 alkoxyphenyl-thio group, C 1 ⁇ C 12 alkyl phenylthio group, 1-naphthylthio group, 2-naphthylthio group and pentafluorophenyl A thio group is mentioned.
  • the arylalkyl group usually has 7 to 60 carbon atoms.
  • the arylalkyl group may have a substituent.
  • substituents are the same as those described above as the substituent of the aryl group.
  • arylalkyl group which may be substituted include a phenyl-C 1 -C 12 alkyl group, a C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkyl group, and a C 1 -C 12 alkylphenyl-C. Examples include 1 to C 12 alkyl groups, 1-naphthyl-C 1 to C 12 alkyl groups, and 2-naphthyl-C 1 to C 12 alkyl groups.
  • the arylalkoxy group usually has 7 to 60 carbon atoms.
  • the arylalkoxy group may have a substituent.
  • substituents are the same as those described above as the substituent of the aryl group.
  • optionally substituted arylalkoxy group include phenyl-C 1 -C 12 alkoxy group, C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkoxy group, C 1 -C 12 alkylphenyl-C Examples include a 1 to C 12 alkoxy group, a 1-naphthyl-C 1 to C 12 alkoxy group, and a 2-naphthyl-C 1 to C 12 alkoxy group.
  • the arylalkylthio group usually has 7 to 60 carbon atoms.
  • the arylalkylthio group may have a substituent.
  • substituents are the same as those described above as the substituent of the aryl group.
  • optionally substituted arylalkylthio group include a phenyl-C 1 -C 12 alkylthio group, a C 1 -C 12 alkoxyphenyl-C 1 -C 12 alkylthio group, and a C 1 -C 12 alkylphenyl-C. Examples include 1 to C 12 alkylthio groups, 1-naphthyl-C 1 to C 12 alkylthio groups, and 2-naphthyl-C 1 to C 12 alkylthio groups.
  • the aromatic heterocyclic group is a group obtained by removing one hydrogen atom on an aromatic ring from an aromatic heterocyclic compound which may have a substituent.
  • the carbon number of the aromatic heterocyclic group is usually 2 to 60.
  • Specific examples of the aromatic heterocyclic group include pyridyl group, furyl group, piperidyl group, quinolyl group, isoquinolyl group, pyrrolyl group, carbazolyl group, and these groups having a substituent.
  • the substituent include a straight-chain alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, and a straight chain having 1 to 20 carbon atoms.
  • Examples thereof include an alkoxy group having a chain or branched alkyl group or a cycloalkyl group having 1 to 20 carbon atoms in its structure.
  • the acyl group means a group obtained by removing a hydroxyl group (OH of —COOH moiety) from carboxylic acid, and is, for example, a group represented by the following formula.
  • R ′ represents an alkyl group which may be substituted with fluorine or an aryl group which may be substituted.
  • Specific examples of the optionally substituted alkyl group and optionally substituted aryl group represented by R ′ include the above-described optionally substituted alkyl group and optionally substituted aryl group. The same.
  • An imide group means a group obtained by removing a hydrogen atom on a nitrogen atom in an imide part from an imide compound, and specific examples are a succinimide group and a phthalimide group.
  • the boric acid ester residue is a group obtained by removing a hydroxyl group from a boric acid diester, and examples of the boric acid diester include dialkyl esters, diaryl esters, diarylalkyl esters and the like. Specific examples of the boric acid ester residue include groups represented by the following formulas.
  • stannyl group examples include a stannyl group, a trichlorostannyl group, a trimethylstannyl group, a triethylstannyl group, a tributylstannyl group, a triphenylstannyl group, and a tribenzylstannyl group.
  • the sulfonic acid residue is a group obtained by removing an acidic hydrogen atom (H of the —SO 3 H moiety) from sulfonic acid.
  • the sulfonic acid include alkanesulfonic acid (for example, methanesulfonic acid, ethanesulfone).
  • the substituent of the condensed ring in which 4 to 10 benzene rings are condensed is preferably an alkyl group or a halogen atom.
  • Examples of the compound having a condensed ring in which 4 to 10 benzene rings are condensed include the following compounds.
  • a preferred embodiment of the compound having a condensed ring in which 4 to 10 benzene rings are condensed is a compound having a pyrene ring.
  • a substituent which this compound has a halogen atom, an alkyl group, and an aryl group are preferable.
  • Another preferred embodiment of the compound having a condensed ring in which 4 to 10 benzene rings are condensed is a compound having a perylene ring.
  • a substituent which this compound has, a halogen atom, an alkyl group, an aryl group, an aryloxy group, and an imide group are preferable.
  • the compound having a condensed ring in which 4 to 10 benzene rings are condensed contained in the organic layer of the organic photoelectric conversion device of the present invention may be one type or two or more types.
  • the conjugated polymer compound used in the organic photoelectric conversion device of the present invention includes (1) a polymer compound substantially composed of a structure in which double bonds and single bonds are alternately arranged, and (2) double bonds and single bonds. Or (3) a structure in which double bonds and single bonds are alternately arranged, and a double bond and single bond through a nitrogen atom.
  • conjugated polymer compound when the repeating units are bonded via a linking group, examples of the linking group include phenylene, biphenyldiyl, naphthalenediyl, anthracenediyl, and the like.
  • the conjugated polymer compound used in the present invention preferably has one or more repeating units selected from the group consisting of formula (2) and formula (3) from the viewpoint of charge transportability. [Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are the same or different and may be substituted with a hydrogen atom or fluorine.
  • Alkyl group optionally substituted fluorine group alkoxy group, optionally substituted fluorine atom substituted alkylthio group, optionally substituted aryl group, optionally substituted aryloxy group, optionally substituted arylthio group Represents an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group or an optionally substituted arylalkylthio group.
  • a fluorine-substituted alkyl group represented by R 1 to R 10 a fluorine-substituted alkoxy group, a fluorine-substituted alkylthio group, a substituted aryl group, a substituted Definition and specifics of aryloxy group which may be substituted, arylthio group which may be substituted, arylalkyl group which may be substituted, arylalkoxy group which may be substituted and arylalkylthio group which may be substituted Examples include a fluorine-substituted alkyl group, a fluorine-substituted alkoxy group, a fluorine-substituted alkyl compound which may have a compound having a condensed ring in which 4 to 10 benzene rings are condensed.
  • the conjugated polymer compound preferably has a polystyrene-equivalent weight average molecular weight of 5 ⁇ 10 2 to 1 ⁇ 10 7 from the viewpoint of film forming ability and solubility in a solvent, and is preferably 1 ⁇ 10 3 to 1 ⁇ . 10 6 is more preferable.
  • the conjugated polymer compound contained in the organic layer of the organic photoelectric conversion element of the present invention may be one type or two or more types.
  • the conjugated polymer compound is prepared by synthesizing a monomer having a functional group suitable for the polymerization reaction used for its production, and then, if necessary, dissolving the monomer in an organic solvent to obtain an alkali or a suitable catalyst. It can be produced by polymerizing the monomer by a known polymerization method such as aryl coupling using a ligand.
  • the organic layer of the organic photoelectric conversion device of the present invention includes a compound having a condensed ring in which 4 to 10 benzene rings are condensed and a conjugated polymer compound.
  • the weight of the compound having a condensed ring in which 4 to 10 benzene rings are condensed in the organic layer is preferably 0.1 to 10000 parts by weight, more preferably 1 to 100 parts by weight with respect to 100 parts by weight of the conjugated polymer compound. 1000 parts by weight.
  • the organic layer of the organic photoelectric conversion device of the present invention may contain only a compound having a condensed ring in which 4 to 10 benzene rings are condensed and a conjugated polymer compound, and further contains an electron-accepting compound. It may be.
  • Examples of the electron-accepting compound include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and metal complexes of derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and its derivatives, polyfluorene and its derivatives, fullerene and derivatives thereof such as C 60, carbon nanotube, 2,9 Examples include phenanthroline derivatives such as -dimethyl-4,7-diphenyl-1,10-phenanthroline, and fullerene and derivatives thereof are particularly preferable.
  • the weight of the electron accepting compound in the organic layer is 100 parts by weight of the total weight of the compound having a condensed ring in which 4 to 10 benzene rings are condensed and the weight of the conjugated polymer compound. Then, it is preferably 1 to 10,000 parts by weight, and more preferably 10 to 2000 parts by weight.
  • Fullerenes and derivatives thereof include C 60 , C 70 , C 84 and derivatives thereof.
  • the fullerene derivative represents a fullerene having a substituent.
  • Specific examples of the C 60 derivative include the following.
  • Specific examples of the C 70 derivative include the following.
  • the organic layer of the organic photoelectric conversion device of the present invention may further contain an electron donating compound.
  • Examples of the electron donating compound include pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, oligothiophene and derivatives thereof, polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, and aromatic amines in side chains or main chains. And polysiloxane derivatives, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, polyphenylene vinylene and derivatives thereof, and polythienylene vinylene and derivatives thereof.
  • the weight of the electron donating compound in the organic layer is 100 parts by weight of the total weight of the compound having a condensed ring in which 4 to 10 benzene rings are condensed and the weight of the conjugated polymer compound. Then, it is preferably 1 to 100,000 parts by weight, and more preferably 10 to 1000 parts by weight.
  • the organic layer of the organic photoelectric conversion device of the present invention has a compound having a condensed ring in which 4 to 10 benzene rings are condensed, a conjugated polymer compound, and an electron donating property within a range not impairing the charge transport property and the charge injection property. Components other than the compound and the electron-accepting compound may be included.
  • the organic photoelectric conversion device of the present invention has an organic layer containing a pair of electrodes, a compound having a condensed ring in which 4 to 10 benzene rings are condensed between the electrodes, and a conjugated polymer compound.
  • a composition of a compound having a condensed ring in which 4 to 10 benzene rings are condensed and a conjugated polymer compound can be used as an electron-accepting compound or an electron-donating compound.
  • the conjugated polymer compound is an electron donating compound and the other is an electron accepting compound, It may have both functions of a receptor.
  • the composition is preferably used as an electron donating compound. It is preferable that at least one of the pair of electrodes is transparent or translucent.
  • the operation mechanism of the organic photoelectric conversion element will be described. Light energy incident from a transparent or translucent electrode is absorbed by the electron-accepting compound and / or the electron-donating compound to generate excitons in which electrons and holes are combined. When the generated excitons move and reach the heterojunction interface where the electron-accepting compound and the electron-donating compound are adjacent to each other, electrons and holes are separated due to the difference in HOMO energy and LUMO energy at the interface. Electric charges (electrons and holes) that can move are generated. The generated charges can be taken out as electric energy (current) by moving to the electrodes.
  • Voc open-circuit voltage
  • a high value of Voc is one factor that develops high photoelectric conversion efficiency.
  • Specific examples of the organic photoelectric conversion device of the present invention include the following 1. ⁇ 5.
  • the organic photoelectric conversion element of this is mentioned. 1. A first organic layer containing a pair of electrodes, a compound having a condensed ring in which 4 to 10 benzene rings are condensed between the electrodes, and a conjugated polymer compound; and provided adjacent to the first organic layer An organic photoelectric conversion device having a second organic layer containing the obtained electron donating compound; 2.
  • An organic photoelectric conversion device having a pair of electrodes and an organic layer containing a compound having a condensed ring in which 4 to 10 benzene rings are condensed between the electrodes, a conjugated polymer compound, and an electron-accepting compound; 5.
  • An organic photoelectric conversion element comprising a pair of electrodes and at least one organic layer containing a compound having a condensed ring in which 4 to 10 benzene rings are condensed between the electrodes, a conjugated polymer compound, and an electron accepting compound.
  • An organic photoelectric conversion element in which the electron-accepting compound is a fullerene derivative; In addition, said 5.
  • the weight of the fullerene derivative in the organic layer is 100 parts by weight of the total of the weight of the compound having a condensed ring in which 4 to 10 benzene rings are condensed and the weight of the conjugated polymer compound
  • the amount is preferably 10 to 1000 parts by weight, and more preferably 50 to 500 parts by weight.
  • the organic photoelectric conversion element of the present invention 3. 4. 5. From the standpoint of including a large number of heterojunction interfaces, the above organic photoelectric conversion element is preferable.
  • the organic photoelectric conversion element is more preferable.
  • an additional layer may be provided between at least one electrode and the organic layer in the element.
  • the additional layer examples include a charge transport layer that transports holes or electrons.
  • the electron acceptor suitably used for the organic photoelectric conversion element is a HOMO of the electron acceptor.
  • the energy is higher than the HOMO energy of the conjugated polymer compound and the HOMO energy of the compound having a condensed ring in which 4 to 10 benzene rings are condensed, and the LUMO energy of the electron acceptor is the LUMO energy and benzene ring of the conjugated polymer compound.
  • an electron donor preferably used for an organic photoelectric conversion element is an electron donor.
  • the HOMO energy of the conjugated polymer compound is lower than the HOMO energy of the conjugated polymer compound and the HOMO energy of the compound having a condensed ring in which 4 to 10 benzene rings are condensed, and the LUMO energy of the electron donor is the LUMO energy of the conjugated polymer compound.
  • the organic photoelectric conversion element of the present invention is usually formed on a substrate.
  • the substrate may be any substrate that does not chemically change when an electrode is formed and an organic layer is formed.
  • the material for the substrate include glass, plastic, polymer film, and silicon.
  • the opposite electrode that is, the electrode far from the substrate
  • the opposite electrode is preferably transparent or translucent.
  • a material of the pair of electrodes a metal, a conductive polymer, or the like can be used, and one of the pair of electrodes is preferably a material having a low work function.
  • metals such as lithium, sodium, potassium, rubidium, cesium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and two of them
  • One or more alloys, or one or more of them and an alloy of one or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, graphite, or a graphite intercalation compound are used. It is done.
  • the alloy examples include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy.
  • the material of the transparent or translucent electrode include a conductive metal oxide film and a translucent metal thin film. Specifically, a film formed using a conductive material made of indium oxide, zinc oxide, tin oxide, and indium tin oxide (ITO), indium zinc oxide, etc., which is a composite thereof, NESA Gold, platinum, silver, and copper are used, and ITO, indium / zinc / oxide, and tin oxide are preferable.
  • Examples of the method for producing the electrode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and the like.
  • organic transparent conductive films such as polyaniline and its derivative (s), polythiophene, and its derivative (s) as an electrode material.
  • the charge transport layer As the material used for the charge transport layer as the additional layer, that is, the hole transport layer and the electron transport layer, the aforementioned electron donating compound and electron accepting compound can be used, respectively.
  • As a material used for the buffer layer as an additional layer an alkali metal such as lithium fluoride, an alkaline earth metal halide, an oxide, or the like can be used.
  • an organic thin film containing a compound having a condensed ring in which 4 to 10 benzene rings are condensed and a conjugated polymer compound can be used as the organic layer in the organic photoelectric conversion element of the present invention.
  • the organic thin film generally has a thickness of 1 nm to 100 ⁇ m, preferably 2 nm to 1000 nm, more preferably 5 nm to 500 nm, and further preferably 20 nm to 200 nm.
  • a polymer other than the conjugated polymer compound can be mixed and used.
  • the organic layer contained in the organic photoelectric conversion device of the present invention can be produced using a composition of a compound having a condensed ring in which 4 to 10 benzene rings are condensed and a conjugated polymer compound.
  • the organic layer when the organic layer further contains an electron-accepting compound, it can be produced using a composition of a compound having a condensed ring in which 4 to 10 benzene rings are condensed, a conjugated polymer compound, and an electron-accepting compound. it can.
  • the organic layer when the organic layer further contains an electron donating compound, it is produced using a composition comprising a compound having a condensed ring in which 4 to 10 benzene rings are condensed, a conjugated polymer compound and an electron donating compound. be able to.
  • the weight of the compound having a condensed ring in which 4 to 10 benzene rings are condensed in the composition is preferably 0.1 to 10000 parts by weight, more preferably 1 to 100 parts by weight of the conjugated polymer compound.
  • the weight of the electron accepting compound in the composition is the sum of the weight of the compound having a condensed ring in which 4 to 10 benzene rings are condensed and the weight of the conjugated polymer compound. Is 100 parts by weight, preferably 1 to 10,000 parts by weight, more preferably 10 to 2000 parts by weight.
  • the weight of the electron donating compound in the composition is the sum of the weight of the compound having a condensed ring in which 4 to 10 benzene rings are condensed and the weight of the conjugated polymer compound.
  • Is 100 to 100 parts by weight preferably 1 to 100,000 parts by weight, and more preferably 10 to 1000 parts by weight.
  • the method for producing the organic thin film is not particularly limited, and examples thereof include a method by film formation from a solution containing the composition and a solvent, but the thin film may be formed by a vacuum deposition method.
  • Examples of a method for producing an organic thin film by film formation from a solution include a method of producing an organic thin film by applying the solution on one electrode and then evaporating the solvent.
  • the solvent used for film formation from a solution is not particularly limited as long as it dissolves a compound having a condensed ring in which 4 to 10 benzene rings are condensed and a conjugated polymer compound.
  • solvent examples include hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexyl, butylbenzene, sec-butylbesen, and tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, and bromobutane.
  • hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexyl, butylbenzene, sec-butylbesen, and tert-butylbenzene
  • carbon tetrachloride chloroform
  • dichloromethane dichloroethane
  • chlorobutane chlorobutane
  • bromobutane bromobutane
  • Aliphatic halogenated hydrocarbon solvents such as chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, aromatic halogenated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, tetrahydrofuran, tetrahydropyran, etc. Of ether solvents.
  • the composition of the compound having a condensed ring in which 4 to 10 benzene rings are condensed and the conjugated polymer compound used in the present invention can be usually dissolved in the solvent in an amount of 0.1% by weight or more.
  • spin coating method For film formation from solution, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic method Coating methods such as a printing method, an offset printing method, an ink jet printing method, a dispenser printing method, a nozzle coating method, a capillary coating method can be used, and a spin coating method, a flexographic printing method, an ink jet printing method, and a dispenser printing method are preferable.
  • the organic photoelectric conversion element By irradiating light such as sunlight from a transparent or translucent electrode, the organic photoelectric conversion element generates a photovoltaic force between the electrodes and can be operated as an organic thin film solar cell.
  • It can also be used as an organic thin film solar cell module by integrating a plurality of organic thin film solar cells.
  • a photocurrent flows and it can be operated as an organic photosensor.
  • It can also be used as an organic image sensor by integrating a plurality of organic photosensors.
  • the molecular weight of the conjugated polymer compound was determined by GPC Laboratories GPC (PL-GPC2000).
  • the conjugated polymer compound was dissolved in o-dichlorobenzene to a concentration of about 1% by weight.
  • As the mobile phase of GPC o-dichlorobenzene was used and allowed to flow at a measurement temperature of 140 ° C. at a flow rate of 1 mL / min.
  • the column three PLGEL 10 ⁇ m MIXED-B (manufactured by PL Laboratory) were connected in series.
  • conjugated polymer compound 1 a pentathienyl-fluorene copolymer represented by the following (hereinafter referred to as “conjugated polymer compound 1”) was obtained.
  • the conjugated polymer compound 1 had a polystyrene-equivalent number average molecular weight of 5.4 ⁇ 10 4 and a polystyrene-equivalent weight average molecular weight of 1.1 ⁇ 10 5 .
  • Example 1 (Production and Evaluation of Organic Thin Film Solar Cell) The conjugated polymer compound 1 was dissolved in o-dichlorobenzene at a concentration of 0.5% (weight%). Thereafter, C60PCBM (phenyl C61-butyric acid methyl ester, trade name E100, manufactured by Frontier Carbon Co., Ltd.) 3 times the weight of conjugated polymer compound 1 was mixed into the solution as an electron acceptor.
  • C60PCBM phenyl C61-butyric acid methyl ester, trade name E100, manufactured by Frontier Carbon Co., Ltd.
  • an equal weight of the compound (E) was mixed into the solution with respect to the weight of the conjugated polymer compound 1.
  • the solution was filtered through a Teflon (registered trademark) filter having a pore size of 1.0 ⁇ m to prepare a coating solution.
  • a glass substrate provided with an ITO film with a thickness of 150 nm by a sputtering method was subjected to surface treatment by ozone UV treatment.
  • the coating solution was applied onto the ITO film by spin coating to obtain an active layer (film thickness of about 100 nm) of the organic thin film solar cell.
  • lithium fluoride was vapor-deposited with a thickness of 4 nm by a vacuum vapor deposition machine, and then Al was vapor-deposited with a thickness of 100 nm.
  • the degree of vacuum at the time of vapor deposition was 1 to 9 ⁇ 10 ⁇ 3 Pa in all cases.
  • the shape of the obtained organic thin-film solar cell was a regular square of 2 mm ⁇ 2 mm.
  • the organic thin film solar cell obtained was measured with Voc (open end voltage was measured with a solar simulator (trade name OTENTO-SUNII: AM1.5G filter, irradiance 100 mW / cm 2 , manufactured by Spectrometer Co., Ltd.). .
  • Example 2 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin film solar cell was produced in the same manner as in Example 1 except that the compound (F) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Example 3 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin film solar cell was produced in the same manner as in Example 1 except that the compound (G) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Example 4 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin film solar cell was produced in the same manner as in Example 1 except that the compound (H) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Compound H can be synthesized by the method described in US Pat. No. 4,845,223.
  • Comparative Example 1 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin film solar cell was produced in the same manner as in Example 1 except that a compound having a condensed ring in which 4 to 10 benzene rings were condensed was used, and Voc was measured. The measurement results are shown in Table 1.
  • the organic photoelectric conversion element of the present invention exhibits a high open-circuit voltage, the present invention is extremely useful.

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Abstract

L'invention concerne un élément organique de conversion photoélectrique qui comporte une paire d'électrodes et une couche organique disposée entre les électrodes, la couche organique comportant un composé doté d'un cycle fusionné constitué de 4 à 10 cycles benzéniques fusionnés ensemble, de préférence un composé doté d'un cycle pyrène ou un composé doté d'un cycle pérylène, et un composé polymérique conjugué. L'élément organique de conversion photoélectrique est capable d'appliquer une tension élevée en circuit ouvert, d'où son utilité.
PCT/JP2011/060494 2010-05-07 2011-04-22 Élément organique de conversion photoélectrique WO2011138935A1 (fr)

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ITMI20120512A1 (it) * 2012-03-29 2013-09-30 Eni Spa Dispositivo fotovoltaico comprendente fullereni e derivati pirenici
WO2014000860A1 (fr) * 2012-06-29 2014-01-03 Merck Patent Gmbh Polymères contenant des unités structurelles de 2,7-pyrène
RU2532164C1 (ru) * 2013-07-30 2014-10-27 Федеральное государственное автономное образовательное учреждение высшего профессионального образования "Уральский федеральный университет имени первого Президента России Б.Н. Ельцина" Способ синтеза 5,5'-(2,3,7,8-бис-(9н,10н-антрацен-9,10-диил)пирен-1,6-диил)бис(2-додецилтиофена) - мономолекулярного оптического сенсора для обнаружения нитроароматических соединений
RU2532903C1 (ru) * 2013-07-09 2014-11-20 Федеральное государственное автономное образовательное учреждение высшего профессионального образования "Уральский федеральный университет имени первого Президента России Б.Н. Ельцина" Способ синтеза 2-додецил-5-(2,3,7,8-бис-(9н,10н-антрацен-9,10-диил)пирен-1-ил)тиофена - мономолекулярного оптического сенсора для обнаружения нитроароматических соединений
US10550056B2 (en) * 2015-03-19 2020-02-04 Board Of Regents Of The Nevada System Of Higher Education, On Behalf Of The University Of Nevada, Reno Aryl compounds and polymers and methods of making and using the same

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JP2007335760A (ja) * 2006-06-16 2007-12-27 Fujifilm Corp 光電変換膜、並びに、該光電変換膜を含む太陽電池、光電変換素子、又は撮像素子
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WO2014000860A1 (fr) * 2012-06-29 2014-01-03 Merck Patent Gmbh Polymères contenant des unités structurelles de 2,7-pyrène
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RU2532164C1 (ru) * 2013-07-30 2014-10-27 Федеральное государственное автономное образовательное учреждение высшего профессионального образования "Уральский федеральный университет имени первого Президента России Б.Н. Ельцина" Способ синтеза 5,5'-(2,3,7,8-бис-(9н,10н-антрацен-9,10-диил)пирен-1,6-диил)бис(2-додецилтиофена) - мономолекулярного оптического сенсора для обнаружения нитроароматических соединений
US10550056B2 (en) * 2015-03-19 2020-02-04 Board Of Regents Of The Nevada System Of Higher Education, On Behalf Of The University Of Nevada, Reno Aryl compounds and polymers and methods of making and using the same
AU2016232761B2 (en) * 2015-03-19 2020-09-17 Nevada Research & Innovation Corporation Aryl compounds and polymers and methods of making and using the same
US11174211B2 (en) 2015-03-19 2021-11-16 Nevada Research & Innovation Corporation Aryl compounds and polymers and methods of making and using the same

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