Title:
METHANOFULLERENE DERIVATIVES AND PHOTOELECTRIC CONVERSION ELEMENTS USING SAME
Document Type and Number:
WIPO Patent Application WO/2011/010526
Kind Code:
A1
Abstract:
Provided are novel methanofullerene derivatives which can be applied as organic semiconductor materials to electronic elements such as organic FET and electroluminescent elements or solar cells. Specifically provided are methanofullerene derivatives represented by general formula (I), which are characterized in that the average of the chemical shift values of C2 and C2 in 13C-NMR is 80.10ppm or more, C2 and C2 being carbon atoms which are present on a fullerene (FL) and which are bonded to C1. In general formula (I), FL is a fullerene; X1 and X2 are each an aromatic hydrocarbon group, an alkyl group, or the like; C2 and C2 are carbon atoms which are present on FL and to which C1 is bonded; and n is an integer of 1 to 10.
Inventors:
OHNO TOSHINOBU (JP)
TAKAO YUKO (JP)
MORIWAKI KAZUYUKI (JP)
MATSUMOTO FUKASHI (JP)
UCHIDA SOUICHI (JP)
IKEDA SATORU (JP)
TAKAO YUKO (JP)
MORIWAKI KAZUYUKI (JP)
MATSUMOTO FUKASHI (JP)
UCHIDA SOUICHI (JP)
IKEDA SATORU (JP)
Application Number:
PCT/JP2010/060844
Publication Date:
January 27, 2011
Filing Date:
June 25, 2010
Export Citation:
Assignee:
OSAKA MUNICIPAL TECHNICAL RSEARCH INST (JP)
NIPPON OIL CORP (JP)
OHNO TOSHINOBU (JP)
TAKAO YUKO (JP)
MORIWAKI KAZUYUKI (JP)
MATSUMOTO FUKASHI (JP)
UCHIDA SOUICHI (JP)
IKEDA SATORU (JP)
NIPPON OIL CORP (JP)
OHNO TOSHINOBU (JP)
TAKAO YUKO (JP)
MORIWAKI KAZUYUKI (JP)
MATSUMOTO FUKASHI (JP)
UCHIDA SOUICHI (JP)
IKEDA SATORU (JP)
International Classes:
C07C13/68; C07D333/10; C07D333/24; H01L51/42
Domestic Patent References:
| WO2008006071A2 | 2008-01-10 | |||
| WO2009087948A1 | 2009-07-16 |
Foreign References:
| JP2009196965A | 2009-09-03 | |||
| US5331183A | 1994-07-19 | |||
| JP2009057356A | 2009-03-19 |
Other References:
MAYOROVA, JULIA YU. ET AL.: "Synthesis and investiagtion of fulleren-based acceptor materials", MENDELEEV COMMUNICATIONS, vol. 17, no. 3, May 2007 (2007-05-01), pages 175 - 177, XP022095747
ZHANG YONG ET AL.: "A Simple and Effective Way of Achieving Highly Efficient and Thermally Stable Bulk-Heterojunction Polymer Solar Cells Using Amorphous Fullerene Derivatives as Electron Acceptor", CHEMISTRY OF MATERIALS, vol. 21, no. 13, 14 July 2009 (2009-07-14), pages 2598 - 2600, XP008149307
KITAMURA, HIROSHI ET AL.: "Stereoelectronic Effects in Diastereoselective Formation of Fulleroids", ORGANIC LETTERS, vol. 9, no. 20, 2007, pages 4045 - 4048, XP008149411
TADA, TOMOYUKI ET AL.: "Synthesis and Reactions of 2,2-[60]Fullerenoalkanoyl Chlorides", JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 4, 2006, pages 1633 - 1639, XP008149311
CHUNHE YANG ET AL.: "Thinner-film plastic photovoltaic cells based on different C60 derivatives", POLYMERS FOR ADVANCED TECHNOLOGIES, vol. 17, no. 7-8, 2006, pages 500 - 505, XP008149414
PAVEL A. TROSHIN ET AL.: "Cover Picture: Sustainable Conversion of Glucose into Hydrogen Peroxide in a Solid Polymer Electrolyte Microbial Fuel Cell (ChemSusChem 3/2010)", CHEMSUSCHEM, vol. 3, March 2010 (2010-03-01), pages 356 - 366, XP008149303
N.S. SARICIFTCI; L. SMILOWITZ; A.J. HEEGER; F. WUDL, SCIENCE, vol. 258, 1992, pages 1474 - 1476
C.J. BRABEC; F. PADINGER; N.S. SARICIFTCI; J.C. HUMMELEN, JOURNAL OF APPLIED PHYSICS, vol. 85, 1999, pages 6866
F. PADINGER; R.S. RITTBERGER; N.S. SARICIFTCI, ADVANCED FUNCTIONAL MATERIAL, vol. 13-1, 2003, pages 85 - 88
M. R-REYES; K. KIM; D.L. CARROLL, APPLIED PHYSICS LETTERS, vol. 87, 2005, pages 083506
W. MA; C. YANG; X. GONG; K. LEE; A.J. HEEGER, ADVANCED FUNCTIONAL MATERIAL, vol. 15, pages 1617 - 1622
F.B. KOOISTRA; J. KNOL; F. KASTENBERG; L.M. POPESCU; W.J.H. VERHEES; J.M. KROON, ORGANIC LETTERS, vol. 9, 2007, pages 551 - 554
J.C. HUMMELEN; B.W. KNIGHT; F. LEPEQ; F. WUDL, JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 60, 1995, pages 532 - 538
See also references of EP 2468704A4
ZHANG YONG ET AL.: "A Simple and Effective Way of Achieving Highly Efficient and Thermally Stable Bulk-Heterojunction Polymer Solar Cells Using Amorphous Fullerene Derivatives as Electron Acceptor", CHEMISTRY OF MATERIALS, vol. 21, no. 13, 14 July 2009 (2009-07-14), pages 2598 - 2600, XP008149307
KITAMURA, HIROSHI ET AL.: "Stereoelectronic Effects in Diastereoselective Formation of Fulleroids", ORGANIC LETTERS, vol. 9, no. 20, 2007, pages 4045 - 4048, XP008149411
TADA, TOMOYUKI ET AL.: "Synthesis and Reactions of 2,2-[60]Fullerenoalkanoyl Chlorides", JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 4, 2006, pages 1633 - 1639, XP008149311
CHUNHE YANG ET AL.: "Thinner-film plastic photovoltaic cells based on different C60 derivatives", POLYMERS FOR ADVANCED TECHNOLOGIES, vol. 17, no. 7-8, 2006, pages 500 - 505, XP008149414
PAVEL A. TROSHIN ET AL.: "Cover Picture: Sustainable Conversion of Glucose into Hydrogen Peroxide in a Solid Polymer Electrolyte Microbial Fuel Cell (ChemSusChem 3/2010)", CHEMSUSCHEM, vol. 3, March 2010 (2010-03-01), pages 356 - 366, XP008149303
N.S. SARICIFTCI; L. SMILOWITZ; A.J. HEEGER; F. WUDL, SCIENCE, vol. 258, 1992, pages 1474 - 1476
C.J. BRABEC; F. PADINGER; N.S. SARICIFTCI; J.C. HUMMELEN, JOURNAL OF APPLIED PHYSICS, vol. 85, 1999, pages 6866
F. PADINGER; R.S. RITTBERGER; N.S. SARICIFTCI, ADVANCED FUNCTIONAL MATERIAL, vol. 13-1, 2003, pages 85 - 88
M. R-REYES; K. KIM; D.L. CARROLL, APPLIED PHYSICS LETTERS, vol. 87, 2005, pages 083506
W. MA; C. YANG; X. GONG; K. LEE; A.J. HEEGER, ADVANCED FUNCTIONAL MATERIAL, vol. 15, pages 1617 - 1622
F.B. KOOISTRA; J. KNOL; F. KASTENBERG; L.M. POPESCU; W.J.H. VERHEES; J.M. KROON, ORGANIC LETTERS, vol. 9, 2007, pages 551 - 554
J.C. HUMMELEN; B.W. KNIGHT; F. LEPEQ; F. WUDL, JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 60, 1995, pages 532 - 538
See also references of EP 2468704A4
Attorney, Agent or Firm:
MORITA NOBUYUKI (JP)
Yoriyuki Morita (JP)
Yoriyuki Morita (JP)
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