WO2011138889A1 - Élément organique de conversion photoélectrique - Google Patents

Élément organique de conversion photoélectrique Download PDF

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WO2011138889A1
WO2011138889A1 PCT/JP2011/059129 JP2011059129W WO2011138889A1 WO 2011138889 A1 WO2011138889 A1 WO 2011138889A1 JP 2011059129 W JP2011059129 W JP 2011059129W WO 2011138889 A1 WO2011138889 A1 WO 2011138889A1
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group
optionally substituted
substituted
formula
fluorine
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上谷　保則
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住友化学株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • 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
    • H10K85/20—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 has the formula (1): (In the formula, T represents an n-valent aromatic group. N represents an integer of 2 to 4. R represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, or a fluorine-substituted group.
  • the organic photoelectric conversion element containing the compound represented by these and a conjugated polymer compound is provided.
  • the organic photoelectric conversion element of the present invention has an organic layer containing the compound represented by the above formula (1) and a conjugated polymer compound.
  • examples of the halogen atom represented by R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the alkyl group represented by R usually has 1 to 20 carbon atoms, and may be linear, branched or cyclic.
  • alkyl group examples 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.
  • the hydrogen atom in the alkyl group may be substituted with a fluorine atom.
  • 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 represented by R usually has 1 to 20 carbon atoms, and the alkyl portion 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.
  • a hydrogen atom in the alkoxy group may be substituted with a fluorine atom.
  • alkoxy group in which a hydrogen atom is substituted with a fluorine atom examples include a trifluoromethoxy group, a pentafluoroethoxy group, a perfluorobutoxy group, a perfluorohexyloxy group, and a perfluorooctyloxy group.
  • the alkylthio group represented by R usually has 1 to 20 carbon atoms, and the alkyl portion may be linear or branched or 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.
  • a hydrogen atom in the alkylthio group may be substituted with a fluorine atom.
  • Examples of the alkylthio group in which a hydrogen atom is substituted with a fluorine atom include a trifluoromethylthio group.
  • the alkoxyalkyl group represented by R usually has 2 to 20 carbon atoms. Specific examples thereof include the formula (9): (In the formula, p represents an integer of 1 to 10, and q represents an integer of 0 to 9.) The group represented by these is mentioned.
  • the aryl group represented by R is an atomic group obtained by removing one hydrogen atom on an aromatic ring from an aromatic hydrocarbon, having a benzene ring, having a condensed ring, independent And those obtained by bonding two or more benzene rings or condensed rings directly or via a group such as vinylene.
  • 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 (6): (In the formula, g represents an integer of 1 to 6, and h represents an integer of 0 to 5.) And an alkoxyalkoxy group represented by the formula:
  • aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, and a linear alkyl group having 1 to 20 carbon atoms.
  • a phenyl group substituted with a branched alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms include C 1 ⁇ C 12 Alkoxyphenyl group (C 1 ⁇ C 12 Indicates that the number of carbon atoms is 1-12. The same applies to the following. ) And pentafluorophenyl groups.
  • a preferred optionally substituted aryl group is C 1 ⁇ C 12 Alkoxyphenyl group and C 1 ⁇ C 12 An alkylphenyl group; C 1 ⁇ C 12 Specific examples of the alkoxyphenyl group include a methoxyphenyl group, an ethoxyphenyl group, a propoxyphenyl group, an isopropoxyphenyl group, a butoxyphenyl group, an isobutoxyphenyl group, a sec-butoxyphenyl group, a tert-butoxyphenyl group, and a pentyloxyphenyl group.
  • alkylphenyl group examples include methylphenyl group, ethylphenyl group, dimethylphenyl group, propylphenyl group, mesityl group, methylethylphenyl group, isopropylphenyl group, butylphenyl group, isobutylphenyl group, sec-butylphenyl group, A tert-butylphenyl group, a pentylphenyl group, an isoamylphenyl group, a hexylphenyl group, a heptylphenyl group, an octylphenyl group, a nonylphenyl group, a decylphenyl group, and a dodecylphenyl group.
  • the aryloxy group represented by R 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 represented by R.
  • Specific examples of the optionally substituted aryloxy group include a phenoxy group, C 1 ⁇ C 12 Alkylphenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, C 1 ⁇ C 12 An alkoxyphenoxy group and a pentafluorophenyloxy group, and C 1 ⁇ C 12 Alkoxyphenoxy group and C 1 ⁇ C 12 Alkylphenoxy groups are preferred.
  • alkoxy examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, Examples include decyloxy, 3,7-dimethyloctyloxy and lauryloxy.
  • alkylphenoxy group examples include methylphenoxy group, ethylphenoxy group, dimethylphenoxy group, propylphenoxy group, 1,3,5-trimethylphenoxy group, methylethylphenoxy group, isopropylphenoxy group, butylphenoxy group, isobutylphenoxy group.
  • the arylthio group represented by R 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 represented by R.
  • Specific examples of the optionally substituted arylthio group include a phenylthio group, C 1 ⁇ C 12 Alkoxyphenylthio group, C 1 ⁇ C 12 Examples thereof include an alkylphenylthio group, a 1-naphthylthio group, a 2-naphthylthio group, and a pentafluorophenylthio group.
  • the arylalkyl group represented by R usually has 7 to 60 carbon atoms.
  • the arylalkyl group may have a substituent.
  • Specific examples of the substituent are the same as those described above as the substituent of the aryl group represented by R.
  • Specific examples of the optionally substituted arylalkyl group include phenyl-C 1 ⁇ C 12 Alkyl group, C 1 ⁇ C 12 Alkoxyphenyl-C 1 ⁇ C 12 Alkyl group, C 1 ⁇ C 12 Alkylphenyl-C 1 ⁇ C 12 Alkyl group, 1-naphthyl-C 1 ⁇ C 12 Alkyl group and 2-naphthyl-C 1 ⁇ C 12 An alkyl group is mentioned.
  • the arylalkoxy group represented by R usually has 7 to 60 carbon atoms.
  • the arylalkoxy group may have a substituent.
  • Specific examples of the substituent are the same as those described above as the substituent of the aryl group represented by R.
  • Specific examples of the 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 1 ⁇ C 12 Alkoxy group, 1-naphthyl-C 1 ⁇ C 12 Alkoxy groups and 2-naphthyl-C 1 ⁇ C 12 An alkoxy group is mentioned.
  • the arylalkylthio group represented by R usually has 7 to 60 carbon atoms.
  • the arylalkylthio group may have a substituent. Specific examples of the substituent are the same as those described above as the substituent of the aryl group represented by R.
  • arylalkylthio group examples include phenyl-C 1 ⁇ C 12 Alkylthio group, C 1 ⁇ C 12 Alkoxyphenyl-C 1 ⁇ C 12 Alkylthio group, C 1 ⁇ C 12 Alkylphenyl-C 1 ⁇ C 12 Alkylthio group, 1-naphthyl-C 1 ⁇ C 12 Alkylthio group and 2-naphthyl-C 1 ⁇ C 12 An alkylthio group is mentioned.
  • the acyl group represented by R is a group obtained by removing a hydroxyl group (OH of the —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 represented by R ′ and the optionally substituted aryl group include the optionally substituted fluorine group represented by R and the optionally substituted aryl group. Same as aryl group.
  • R is preferably a hydrogen atom, an alkyl group or a halogen atom from the viewpoint of charge transportability.
  • T in Formula (1) is an n-valent aromatic group, and represents an n-valent aromatic carbocyclic group or an n-valent aromatic heterocyclic group.
  • An n-valent aromatic carbocyclic group is an n-valent organic group obtained by removing n hydrogen atoms on an aromatic ring from an aromatic carbocyclic compound, and an n-valent aromatic heterocyclic group is an aromatic complex.
  • aromatic carbocyclic compound examples include benzene, naphthalene, anthracene, pyrene, perylene, fluorene, benzofluorene, biphenyl, terphenyl, and these compounds having a substituent.
  • aromatic heterocyclic compound examples include pyrrole, pyridine, indole, imidazole, quinoline, isoquinoline, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran and these compounds having a substituent.
  • substituent of the aromatic carbocyclic compound and aromatic heterocyclic compound include those described above as the substituent of the aryl group represented by R and alkyl groups having 1 to 20 carbon atoms.
  • Examples of the compound represented by the formula (1) include the following compounds. In the formula (1), a preferred embodiment of n is 2.
  • a preferred embodiment of the aromatic group represented by T is the formula (2): (Wherein R 1 Is a hydrogen atom, 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, an alkoxyalkyl group, or an aryl group that may be substituted An optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group or an optionally substituted arylalkylthio group; To express. 4 R 1 May be the same or different. ) It is group represented by these.
  • R 1 A halogen atom represented by: an alkyl group which may be fluorine-substituted, an alkoxy group which may be fluorine-substituted, an alkylthio group which may be fluorine-substituted, an alkoxyalkyl group, an aryl group which may be substituted, Definitions of an optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group, and an optionally substituted arylalkylthio group And specific examples include a halogen atom represented by R, an alkyl group which may be substituted with fluorine, an alkoxy group which may be substituted with fluorine, an alkylthio group which may be substituted with fluorine, an alkoxyalkyl group, substituted Optionally substituted aryl group, optionally substituted aryloxy group, substituted Which may be aryl
  • R 1 are preferably a hydrogen atom or an alkyl group.
  • Another preferred embodiment of the aromatic group represented by T is the formula (3): (Wherein R 2 Is a hydrogen atom, 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, an alkoxyalkyl group, or an aryl group that may be substituted An optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group or an optionally substituted arylalkylthio group; To express.
  • R 2 It is an organic group represented by.
  • R 2 A halogen atom represented by: an alkyl group which may be fluorine-substituted, an alkoxy group which may be fluorine-substituted, an alkylthio group which may be fluorine-substituted, an alkoxyalkyl group, an aryl group which may be substituted, Definitions of an optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group, and an optionally substituted arylalkylthio group And specific examples include a halogen atom represented by R, an alkyl group which may be substituted with fluorine, an alkoxy group which may be substituted with fluorine, an alkylthio group which may be substituted with fluorine, an alkoxyalkyl group, substituted Optionally substituted aryl group
  • R 2 are preferably a hydrogen atom or an alkyl group.
  • Another preferred embodiment of the aromatic group represented by T is the formula (4): (In the formula, A ring and B ring are the same or different and each represents an aromatic carbocyclic ring or an aromatic heterocyclic ring. 2 Represents a divalent group which forms a 5-membered ring or a 6-membered ring by bonding to -S-, -O- or A ring and B ring. ) It is an organic group represented by.
  • examples of the aromatic carbocycles of the A ring and the B ring include a benzene ring, a naphthalene ring, and an anthracene ring.
  • Examples of the aromatic heterocycle include a thiophene ring, a pyridine ring, and a furan ring.
  • the A ring and the B ring are preferably a benzene ring and a naphthalene ring, and more preferably a benzene ring.
  • a 2 Represents a divalent group which forms a 5-membered ring or a 6-membered ring by bonding to -S-, -O- or A ring and B ring.
  • Examples of the divalent group that forms a 5-membered or 6-membered ring include -C (R 4 ) 2 -, -O-C (R 5 ) 2 , -N (R 6 )-, -Si (R 7 ) 2 -, -B (R 8 )-, -C (R 9 ) 2 -C (R 9 ) 2 -Etc. are mentioned.
  • R 4 ⁇ R 9 Are the same or different and each represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted arylalkyl group or a heterocyclic group. 2 R 4 May be the same or different.
  • 2 R 4 may be bonded to each other to form a ring structure.
  • 2 R 5 May be the same or different.
  • 2 R 7 May be the same or different.
  • 4 R 9 May be the same or different.
  • R 4 ⁇ R 9 Definitions and specific examples of the optionally substituted alkyl group, the optionally substituted aryl group, and the optionally substituted arylalkyl group represented by R are as follows: The definition and specific examples of a good alkyl group, an optionally substituted aryl group and an optionally substituted arylalkyl group are the same.
  • R 4 ⁇ R 9 Is generally an aromatic heterocyclic group, and specific examples thereof include an optionally substituted pyridyl group, furyl group, piperidyl group, quinolyl group. , Isoquinolyl group and pyrrolyl group.
  • a 2 Is -C (R 4 ) 2 -, -N (R 6 )-Is preferred.
  • R 4 Is preferably an alkyl group or an aryl group.
  • R 6 Is preferably an alkyl group or an aryl group.
  • R 20 Is a hydrogen atom, 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, an alkoxyalkyl group, or an aryl group that may be substituted
  • R 20 May be the same or different.
  • R 20 A halogen atom represented by: an alkyl group which may be fluorine-substituted, an alkoxy group which may be fluorine-substituted, an alkylthio group which may be fluorine-substituted, an alkoxyalkyl group, an aryl group which may be substituted, Definitions of an optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group, and an optionally substituted arylalkylthio group And specific examples include a halogen atom represented by R, an alkyl group which may be substituted with fluorine, an alkoxy group which may be substituted with fluorine, an alkylthio group which may be substituted with fluorine, an alkoxyalkyl group, substituted Optionally substituted aryl group, optionally substituted aryloxy group, substituted Which may be aryl
  • R 20 are preferably a hydrogen atom or an alkyl group.
  • Another preferred embodiment of the aromatic group represented by T is the formula (21): (Wherein R 21 Is a hydrogen atom, 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, an alkoxyalkyl group, or an aryl group that may be substituted An optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group or an optionally substituted arylalkylthio group; To express.
  • R 21 It is an organic group represented by.
  • R 21 A halogen atom represented by: an alkyl group which may be fluorine-substituted, an alkoxy group which may be fluorine-substituted, an alkylthio group which may be fluorine-substituted, an alkoxyalkyl group, an aryl group which may be substituted, Definitions of an optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group, and an optionally substituted arylalkylthio group And specific examples include a halogen atom represented by R, an alkyl group which may be substituted with fluorine, an alkoxy group which may be substituted with fluorine, an alkylthio group which may be substituted with fluorine, an alkoxyalkyl group, substituted Optionally substituted aryl group
  • R 21 are preferably a hydrogen atom or an alkyl group.
  • n is 4.
  • Another preferred embodiment of the aromatic group represented by T is the formula (5): (Wherein R 3 Is a hydrogen atom, 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, an alkoxyalkyl group, or an aryl group that may be substituted An optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group or an optionally substituted arylalkylthio group; To express.
  • R 3 It is an organic group represented by.
  • R 3 A halogen atom represented by: an alkyl group which may be fluorine-substituted, an alkoxy group which may be fluorine-substituted, an alkylthio group which may be fluorine-substituted, an alkoxyalkyl group, an aryl group which may be substituted, Definitions of an optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group, and an optionally substituted arylalkylthio group And specific examples include a halogen atom represented by R, an alkyl group which may be substituted with fluorine, an alkoxy group which may be substituted with fluorine, an alkylthio group which may be substituted with fluorine, an alkoxyalkyl group, substituted Optionally substituted aryl group
  • R 6 are preferably a hydrogen atom or an alkyl group.
  • the compound represented by the formula (1) 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 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.
  • conjugated polymer compound when the repeating units are bonded via a linking group, examples of the linking group include phenylene, biphenyl-4.4′-diyl, 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 (7) and formula (8) from the viewpoint of charge transportability.
  • R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 And R 19 are the same or different and are a hydrogen atom, an alkyl group which may be substituted with fluorine, an alkoxy group which may be substituted with fluorine, an alkylthio group which may be substituted with fluorine, an alkoxyalkyl group, which may be substituted
  • An aryl group, an optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group or an optionally substituted arylalkylthio Represents a group.
  • R 10 ⁇ R 19 An optionally substituted fluorine-substituted alkyl group, an optionally substituted fluorine-substituted alkoxy group, an optionally substituted fluorine-substituted alkylthio group, an alkoxyalkyl group, an optionally substituted aryl group, Definitions and specific examples of an optionally substituted aryloxy group, an optionally substituted arylthio group, an optionally substituted arylalkyl group, an optionally substituted arylalkoxy group and an optionally substituted arylalkylthio group Is a fluorine-substituted alkyl group, a fluorine-substituted alkoxy group, a fluorine-substituted alkylthio group, a alkoxyalkyl group, or a substituted aryl represented by the aforementioned R.
  • the conjugated polymer compound has a polystyrene-equivalent weight average molecular weight of 5 ⁇ 10 5 from the viewpoint of film forming ability and solubility in a solvent.
  • 2 ⁇ 1 ⁇ 10 7 Is preferably 1 ⁇ 10 3 ⁇ 1 ⁇ 10 6 More preferably, 1 ⁇ 10 4 ⁇ 1 ⁇ 10 6 More preferably.
  • 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 element of the present invention includes a compound represented by the formula (1) and a conjugated polymer compound.
  • the weight of the compound represented by the formula (1) in the organic layer is preferably 0.1 to 10000 parts by weight, more preferably 1 to 1000 parts by weight with respect to 100 parts by weight of the conjugated polymer compound.
  • the organic layer of the organic photoelectric conversion device of the present invention may contain only the compound represented by the formula (1) and the conjugated polymer compound, and may further contain an electron accepting compound.
  • 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 derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene and derivatives thereof, C 60 And phenanthroline derivatives such as carbon nanotubes and 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline.
  • Fullerene and derivatives thereof are particularly preferable.
  • the weight of the electron-accepting compound in the organic layer is 1 to 1 when the total weight of the compound represented by the formula (1) and the weight of the conjugated polymer compound is 100 parts by weight.
  • the amount is preferably 10,000 parts by weight, and more preferably 10 to 2000 parts by weight.
  • Fullerene and its derivatives include C 60 , C 70 , C 84 And derivatives thereof.
  • the fullerene derivative represents a compound in which at least a part of fullerene is modified. Examples of the fullerene derivative include a compound represented by the formula (11), a compound represented by the formula (12), a compound represented by the formula (13), and a compound represented by the formula (14).
  • R a Is a group having an alkyl group which may be substituted with fluorine, an aryl group which may be substituted, an aromatic heterocyclic group or an ester structure. Multiple R a May be the same or different.
  • R b Represents an alkyl group which may be fluorine-substituted or an aryl group which may be substituted. Multiple R b May be the same or different.
  • R a And R b The definition and specific examples of the optionally substituted fluorine group and optionally substituted aryl group represented by the formula are as follows: the optionally substituted fluorine group represented by R and optionally substituted The definition and specific examples of the aryl group are the same.
  • R a In general, the aromatic heterocyclic group represented by the formula has 3 to 60 carbon atoms, and examples thereof include a thienyl group, a pyrrolyl group, a furyl group, a pyridyl group, a piperidyl group, a quinolyl group, and an isoquinolyl group.
  • R c Definitions and specific examples of an optionally substituted alkyl group, an optionally substituted aryl group and an aromatic heterocyclic group represented by a
  • the definition and specific examples of the optionally substituted fluorine-substituted alkyl group, the optionally substituted aryl group and the aromatic heterocyclic group are as follows.
  • C 60 Specific examples of the derivatives include the following.
  • C 70 Specific examples of the derivatives 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 1 to 1 when the total of the weight of the compound represented by the formula (1) and the weight of the conjugated polymer compound is 100 parts by weight.
  • the amount is preferably 100,000 parts by weight, more preferably 10 to 1,000 parts by weight.
  • the organic layer of the organic photoelectric conversion device of the present invention has a compound represented by the formula (1), a conjugated polymer compound, an electron donating compound, and an electron accepting property as long as the charge transporting property and the charge injecting property are not impaired. Components other than the compound may be included.
  • the organic photoelectric conversion element of the present invention has a pair of electrodes and an organic layer containing a compound represented by the formula (1) and a conjugated polymer compound between the electrodes.
  • the composition of the compound represented by the formula (1) and the conjugated polymer compound can be used as an electron accepting compound or an electron donating compound.
  • 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.
  • An organic photoelectric conversion element having a pair of electrodes and an organic layer containing a compound represented by the formula (1), a conjugated polymer compound, and an electron-accepting compound between the electrodes; 5.
  • the weight of the fullerene derivative in the organic layer is 10 to 1000 parts by weight when the total of the weight of the compound represented by the formula (1) and the weight of the conjugated polymer compound is 100 parts by weight.
  • the amount is 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. Examples of the additional layer include a charge transport layer that transports holes or electrons.
  • the electron acceptor suitably used for the organic photoelectric conversion element has a conjugated polymer in which the HOMO energy of the electron acceptor is The HOMO energy of the compound and the HOMO energy of the compound represented by the formula (1) are higher, and the LUMO energy of the electron acceptor is the LUMO energy of the conjugated polymer compound and the LUMO energy of the compound represented by the formula (1) Is a higher compound.
  • the electron donor used suitably for an organic photoelectric conversion element has the HOMO energy of an electron donor.
  • the HOMO energy of the conjugated polymer compound is lower than the HOMO energy of the compound represented by the formula (1), and the LUMO energy of the electron donor is the LUMO energy of the conjugated polymer compound and the compound represented by the formula (1) This is a compound having a lower LUMO energy.
  • 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. Examples of the material for the substrate include glass, plastic, polymer film, and silicon.
  • the opposite electrode that is, the electrode far from the substrate is preferably transparent or translucent.
  • 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.
  • 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 examples 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.
  • the organic thin film containing the compound and conjugated polymer compound which are represented by Formula (1) can be used, for example.
  • 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 low molecular compound and / or a conjugated polymer compound other than the compound represented by the formula (1) as an electron donating compound and / or an electron accepting compound in the organic thin film Polymers other than these can also be mixed and used.
  • the organic layer contained in the organic photoelectric conversion element of the present invention can be produced using a composition of a compound represented by the formula (1) and a conjugated polymer compound.
  • the organic layer further contains an electron-accepting compound it can be produced using a composition of the compound represented by formula (1), a conjugated polymer compound, and an electron-accepting compound.
  • the organic layer further contains an electron donating compound it can be produced by using a composition of a compound represented by the formula (1), a conjugated polymer compound and an electron donating compound.
  • the weight of the compound represented by the formula (1) in the composition is preferably 0.1 to 10000 parts by weight, more preferably 1 to 1000 parts by weight with respect to 100 parts by weight of the conjugated polymer compound. is there.
  • the weight of the electron-accepting compound in the composition is 100 parts by weight of the sum of the weight of the compound represented by formula (1) and the weight of the conjugated polymer compound. Then, it is preferably 1 to 10000 parts by weight, and more preferably 10 to 2000 parts by weight.
  • the weight of the electron donating compound in the composition is 100 parts by weight of the sum of the weight of the compound represented by the formula (1) 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 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 the compound represented by the formula (1) and the 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.
  • ether solvents ether solvents.
  • the composition of the compound represented by formula (1) 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.
  • the compound (E) was mixed with the solution in an equal weight 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.
  • Example 5 (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 (I) produced by the method of Synthesis Example 14 of JP-A-2006-97008 was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Example 6 (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 (J) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Example 7 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin film solar cell was produced in the same manner as in Example 5 except that the amount of compound (J) added was 0.5 times the weight of the conjugated polymer compound 1, and Voc was measured. The measurement results are shown in Table 1.
  • Example 8 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin-film solar cell was prepared in the same manner as in Example 1 except that the compound (K) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Example 9 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin-film solar cell was prepared in the same manner as in Example 1 except that the compound (L) was used instead of the compound (E), and Voc was measured.
  • Example 10 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin-film solar cell was prepared in the same manner as in Example 1 except that the compound (M) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Example 11 (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 (N) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Example 12 (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 (O) was used instead of the compound (E), and Voc was measured.
  • Example 13 (Production and Evaluation of Organic Thin Film Solar Cell) An organic thin-film solar cell was prepared in the same manner as in Example 1 except that the compound (P) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Synthesis Example 2 (Synthesis of Compound (Q-1)) Under an argon atmosphere, 125.0 g (0.379 mol) of 1,4-diiodobenzene, 15.84 g (0.095 mol) of carbazole, and 39.3 g (0.284 mol) of potassium carbonate in a 1000 ml three-necked flask.
  • the reaction product was filtered, and solid content on a filter was wash
  • the filtrate and the washing solution were combined and concentrated under reduced pressure with an evaporator at 70 to 75 ° C. to obtain 132.3 g of a light brown resinous product.
  • the resinous product was purified by silica gel chromatography to obtain 19.7 g of white crystals.
  • the volume ratio of hexane to chloroform was 10. To this crystal, 200 ml of hexane was added, stirred under reflux for 1 hour, and then cooled to room temperature (25 ° C.).
  • the product was filtered, washed with 20 ml of toluene, and then the filtrate was dried under reduced pressure at 70 to 75 ° C. to obtain 3.60 g of a skin-colored solid.
  • This solid was dissolved in 500 ml of tetrahydrofuran under the conditions of 50 to 55 ° C., 4.0 g of activated carbon was added, and the mixture was stirred at 50 to 55 ° C. for 1 hour. Thereafter, the activated carbon was filtered off, and the activated carbon was washed with 30 ml of tetrahydrofuran. Using an evaporator, the filtrate was concentrated under reduced pressure at 75 ° C. to obtain 3.40 g of a white solid.
  • the volume ratio of hexane to chloroform was set to 1.
  • the collected solution was concentrated, and the resulting crude product was repulped with 20 times the weight of toluene with respect to the crude product, and purified again by column chromatography to obtain 2.53 g of the purified product.
  • 500 g of silica gel was used, and a solvent in which hexane and chloroform were mixed was used as a solvent.
  • the volume ratio of hexane to chloroform was 1.
  • the purified product was dissolved in 500 ml of tetrahydrofuran while heating at 50 ° C., 2.3 g of activated carbon was added, and the mixture was further heated and stirred at 50 ° C. for 30 minutes.
  • Example 14 (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 (Q) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Example 15 (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 (R) was used instead of the compound (E), and Voc was measured.
  • Example 16 (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 (T) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • Example 17 (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 (U) was used instead of the compound (E), and Voc was measured. The measurement results are shown in Table 1.
  • 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 the compound represented by the formula (1) was not 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.

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 représenté par la formula (1) (où T représente un groupe aromatique ; n représente un entier de 2 à 4 ; et R représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle, un groupe alcoxy, un groupe alkylthio, un groupe aryle, un groupe aryloxy, un groupe arylthio, un groupe arylalkyle, un groupe arylalcoxy, un groupe arylalkylthio, un groupe acyle ou similaire) et un composé polymérique conjugué. L'élément organique de conversion photoélectrique est capable d'appliquer une tension élevée en circuit ouvert.
PCT/JP2011/059129 2010-05-07 2011-04-06 Élément organique de conversion photoélectrique WO2011138889A1 (fr)

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