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Photoelectric conversion material containing fullerene derivative

外国特許コード F110003820
整理番号 E07905WO
掲載日 2011年7月5日
出願国 アメリカ合衆国
出願番号 29989407
公報番号 20090101200
公報番号 8304643
出願日 平成19年5月2日(2007.5.2)
公報発行日 平成21年4月23日(2009.4.23)
公報発行日 平成24年11月6日(2012.11.6)
国際出願番号 JP2007059811
国際公開番号 WO2007129768
国際出願日 平成19年5月2日(2007.5.2)
国際公開日 平成19年11月15日(2007.11.15)
優先権データ
  • 特願2006-129857 (2006.5.9) JP
  • 2007JP059811 (2007.5.2) WO
発明の名称 (英語) Photoelectric conversion material containing fullerene derivative
発明の概要(英語) The present invention provides a photoelectric conversion material comprising a fullerene derivative represented by the formula C60(R1)5(MLn), wherein: each R1 independently represents an organic group having a substituent; M represents a metal atom; L is a ligand of M; and n is the number of Ls.
Further, the present invention also provides a photoelectric conversion device having a self-assembled monomolecular film of the photoelectric conversion material, and a solar cell having the photoelectric conversion device.
従来技術、競合技術の概要(英語) BACKGROUND ART
Since the method for synthesizing a carbon cluster (hereinafter also referred to as "fullerene"), in which carbon atoms are arranged to form a spherical shape or a rugby ball shape, was established, fullerene has been energetically studied.
As a result, many fullerene derivatives have been synthesized.
In general, fullerene derivatives have a widely-extended pi electron system.
Further, characteristically, fullerene derivatives have a relatively small HOMO-LUMO gap (about 1.5-2.0 eV), and also have optical absorption property in a wide wavelength range and highly-efficient light-emitting property via Singlet-to-Triplet intersystem crossing.
Further, fullerenes are constituted only by carbon atoms, and at the same time, exhibit multistep reversible redox reaction (6-electron reduction).
Attributed to these properties, there are wide range of possibilities for application of fullerene derivatives.
For example, it is thought that fullerene derivatives can be utilized for FET, organic EL, solar cells, catalysts, etc.
Regarding a photoelectric conversion device utilizing optical absorption property of fullerene metal complexes, studies of the development of artificial photosynthesis utilizing high electron acceptor ability of fullerenes have been reported.
Specifically, there are the following reports: a wet solar cell comprising a monomolecular film prepared by molecules, which are joined via chemical bond using ferrocene (electron donor)-porphyrin (optical absorption center)-fullerene (electron acceptor) on a gold electrode [Eur. J. Org. Chem. 2445. (1999) (non-patent document 1)]; and a wet solar cell, wherein molecules in which fullerene metal complex and porphyrin are joined together are immobilized on an ITO electrode [J.
Am. Chem. Soc. 127, 2380, (2005) (non-patent document 2)].
However, regarding such solar cells, synthesis of fullerene derivatives to be used in photoelectric conversion devices thereof is complicated.
In addition, there is a problem that desired properties cannot be sufficiently exerted.

特許請求の範囲(英語) [claim1]
1. A photoelectric conversion device having a self-assembled monomolecular film of a photoelectric conversion material comprising a fullerene derivative represented by the following formula (1):
wherein: each R1 independently represents an organic group having a substituent; M represents a metal atom; L is a ligand of M; and n is the number of Ls.
[claim2]
2. A solar cell having the photoelectric conversion device according to claim 1.
[claim3]
3. A photoelectric conversion material comprising a fullerene derivative represented by the following formula (11):
wherein:
each R2 is independently a group represented by the following formula (A):
wherein: X1 represents a carboxylic acid group, a phosphate group or a phosphonate group; each R20 independently represents an organic group; and n is an integer from 0 to 4; and M represents a metal atom.
[claim4]
4. A photoelectric conversion material comprising a fullerene derivative represented by the following formula (12):
wherein:
each R3 is independently a group represented by the following formula (B):
wherein: X1 represents a carboxylic acid group, a phosphate group, a phosphonate group; each R20 independently represents an organic group; n is an integer from 0 to 4; and m is an integer from 0 to 4; and M represents a metal atom.
[claim5]
5. A photoelectric conversion device having a self-assembled monomolecular film of a photoelectric conversion material comprising a fullerene derivative represented by the following formula (10):
wherein: each R1 independently represents a C1-C30 hydrocarbon group, a C1-C30 alkoxy group, a C6-C30 aryloxy group, an amino group, a silyl group, an alkylthio group ( -- SY1: in the formula, Y1 represents a substituted or unsubstituted group C1-C30 alkyl group), an arylthio group ( -- SY2: in the formula, Y2 represents a substituted or unsubstituted C6-C18 aryl group), an alkylsulfonyl group ( -- SO2Y3: in the formula, Y3 represents a substituted or unsubstituted C1C30 alkyl group), or an arylsulfonyl group ( -- SO2Y4: in the formula, Y4 represents a substituted or unsubstituted C6-C18 aryl group), which has a carboxylic acid group, a phosphate group, or a phosphonate group; and M represents a metal atom.
[claim6]
6. A photoelectric conversion device having an ITO electrode on which the self-assembled monomolecular film of a photoelectric conversion material is formed and wherein the photoelectric conversion material comprises a fullerene derivative represented by the following formula (10):
wherein: each R1 independently represents a C1-C30 hydrocarbon group; a C1-C30 alkoxy group, a C6-C30 aryloxy group, an amino group, a silyl group, an alkylthio group ( -- SY1: in the formula, Y1 represents a substituted or unsubstituted C1-C30 alkyl group), an arylthio group ( -- SY2: in the formula, Y2 represents a substituted or unsubstituted C6-C18 aryl group), an alkylsulfonyl group ( -- SO2Y3: in the formula, Y3 represents a substituted or unsubstituted C1-C30 alkyl group), or an arylsulfonyl group ( -- SO2Y4: in the formula, Y4 represents a substituted or unsubstituted C6-C18 aryl group), which has a carboxylic acid group, a phosphate group, or a phosphonate group; and M represents a metal atom.
[claim7]
7. A solar cell having the photoelectric conversion device according to claim 5 or 6.
[claim8]
8. A photoelectric conversion device having a self-assembled monomolecular film of a photoelectric conversion material comprising a fullerene derivative represented by the following formula (10):
wherein: each R1 independently represents a C1-C30 hydrocarbon group, a C1-C30 alkoxy group, a C6-C30 aryloxy group, an amino group, a silyl group, an alkylthio group ( -- SY1: in the formula, Y1 represents a substituted or unsubstituted C1-C30 alkyl group), an arylthio group ( -- SY2: in the formula, Y2 represents a substituted or unsubstituted C6-C18 aryl group), an alkylsulfonyl group ( -- SO2Y3: in the formula, Y3 represents a substituted or unsubstituted C1-C30 alkyl group), or an arylsulfonyl group ( -- SO2Y4: in the formula, Y4 represents a substituted or unsubstituted C6-C18 aryl group), which has a thiol group or a disulfide group; and M represents a metal atom.
[claim9]
9. A photoelectric conversion device having a gold electrode on which a self-assembled monomolecular film of a photoelectric conversion material is formed and wherein the photoelectric conversion material comprises a fullerene derivative represented by the following formula (10):
wherein: each R1 independently represents a C1-C30 hydrocarbon group, a C1-C30 alkoxy group, a C6-C30 aryloxy group, an amino group, a silyl group, an alkylthio group ( -- SY1: in the formula, Y1 represents a substituted or unsubstituted C1-C30 alkyl group), an arylthio group ( -- SY2: in the formula, Y2 represents a substituted or unsubstituted C6-C18 aryl group), an alkylsulfonyl group ( -- SO2Y3: in the formula, Y3 represents a substituted or unsubstituted C1-C30 alkyl group), or an arylsulfonyl group ( -- SO2Y4: in the formula, Y4 represents a substituted or unsubstituted C6-C18 aryl group), which has a thiol group or a disulfide group; and M represents a metal atom.
[claim10]
10. A solar cell having the photoelectric conversion device according to claim 8.
[claim11]
11. A photoelectric conversion device having a self-assembled monomolecular film of a photoelectric conversion material comprising a fullerene derivative represented by the following formula (10):
wherein: each R1 independently represents a C1-C30 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C4-C30 alkyldienyl group, C6-C18 aryl group, a C7-C30 arylalkyl group, a C7-C30 cycloalkyl group, or a C4- C30 cycloalkenyl group, which has a thiol group or a disulfide group; and M represents a metal atom.
[claim12]
12. A photoelectric conversion device having a gold electrode on which a self-assembled monomolecular film of a photoelectric conversion material is formed and wherein the photoelectric conversion material comprises a fullerene derivative represented by the following formula (10):
wherein: each R1 independently represents a C1-C30 alkly group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C4-C30 alkyldienyl group, a C6-C18 aryl group, a C7-C30 alkylaryl group, a C7-C30 arylalkyl group, a C4-C30 cycloalkyl group or a C4-C30 cycloalkenyl group, which has a thiol group or a disulfide group; and M represents a metal atom.
[claim13]
13. A solar cell having the photoelectric conversion device according to claim 9.
  • 発明者/出願人(英語)
  • NAKAMURA EIICHI
  • MATSUO YUTAKA
  • KANAIZUKA KATSUHIKO
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
米国特許分類/主・副
  • 136/243
  • 136/252
  • 556/136
  • 556/143
参考情報 (研究プロジェクト等) ERATO NAKAMURA Functional Carbon Cluster AREA
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