Title:
COMPOUND, HOLE TRANSPORT MATERIAL, AND PHOTOELECTRIC CONVERSION ELEMENT INCLUDING SAME
Document Type and Number:
WIPO Patent Application WO/2022/153962
Kind Code:
A1
Abstract:
The problem to be solved by the present invention is to provide: a compound useful as a hole transport material for photoelectric conversion elements whereby electric current can be efficiently taken out; and a photoelectric conversion element and a solar cell which have satisfactory photoelectric conversion characteristics and include a hole transport layer comprising the compound. This compound is represented by general formula (1). In the formula, R1 to R20 each represent a hydrogen atom, a C1-C20 alkoxy group, etc., and Y represents an oxygen atom or CR21R22 (R21 and R22 each represent a nitryl group, a C1-C10 acyl group, etc.).
Inventors:
OHKURA YUYA (JP)
TAKAHASHI HIDEAKI (JP)
SATO HIROSHI (JP)
TAKAHASHI HIDEAKI (JP)
SATO HIROSHI (JP)
Application Number:
PCT/JP2022/000486
Publication Date:
July 21, 2022
Filing Date:
January 11, 2022
Export Citation:
Assignee:
HODOGAYA CHEMICAL CO LTD (JP)
International Classes:
C07C225/22; C07C229/44; C07C255/42; C07D209/88; C07D239/66; C07D265/38; C07D279/22; C07D333/22; C07D333/24; C07D409/14; H01L51/46
Foreign References:
| CN110627667A | 2019-12-31 | |||
| CN102214800A | 2011-10-12 | |||
| CN108586289A | 2018-09-28 | |||
| CN106467529A | 2017-03-01 | |||
| CN107046100A | 2017-08-15 | |||
| CN113087726A | 2021-07-09 | |||
| US10937972B2 | 2021-03-02 |
Other References:
CAO YULIN, CHEN WEI, SUN HUILIANG, WANG DONG, CHEN PENG, DJURIŠIĆ ALEKSANDRA B., ZHU YUDONG, TU BAO, GUO XUGANG, TANG BEN-ZHONG, H: "Efficient Perovskite Solar Cells with a Novel Aggregation‐Induced Emission Molecule as Hole‐Transport Material", SOLAR RRL, vol. 4, no. 2, 1 February 2020 (2020-02-01), pages 1900189, XP055950147, ISSN: 2367-198X, DOI: 10.1002/solr.201900189
YU XINYU, LI ZHEN, SUN XIANGLANG, ZHONG CHENG, ZHU ZONGLONG, LI ZHONG’AN, JEN ALEX K.-Y.: "Dopant-free dicyanofluoranthene-based hole transporting material with low cost enables efficient flexible perovskite solar cells", NANO ENERGY, ELSEVIER, NL, vol. 82, 1 April 2021 (2021-04-01), NL , pages 105701, XP055950150, ISSN: 2211-2855, DOI: 10.1016/j.nanoen.2020.105701
GAO, Z.Q. ; XIA, P.F. ; LO, P.K. ; MI, B.X. ; TAM, H.L. ; WONG, M.S. ; CHEAH, K.W. ; CHEN, C.H.: "p-Doped p-phenylenediamine-substituted fluorenes for organic electroluminescent devices", ORGANIC ELECTRONICS, ELSEVIER, AMSTERDAM, NL, vol. 10, no. 4, 1 July 2009 (2009-07-01), AMSTERDAM, NL, pages 666 - 673, XP026119399, ISSN: 1566-1199, DOI: 10.1016/j.orgel.2009.02.025
ZHONG HU; VEDBAR S. KHADKA; WEI WANG; DAVID W. GALIPEAU; XINGZHONG YAN: "Theoretical study of two-photon absorption properties and up-conversion efficiency of new symmetric organic π-conjugated molecules for photovoltaic devices", JOURNAL OF MOLECULAR MODELING, SPRINGER, DE, vol. 18, no. 8, 23 February 2012 (2012-02-23), DE , pages 3657 - 3667, XP035091276, ISSN: 0948-5023, DOI: 10.1007/s00894-012-1378-3
WIELOPOLSKI MATEUSZ, MARSZALEK MAGDALENA, BRUNETTI FULVIO G., JOLY DAMIEN, CALBO JOAQUÍN, ARAGÓ JUAN, MOSER JACQUES-E., HUMPHRY-BA: "Synthesis and optoelectronic properties of chemically modified bi-fluorenylidenes", JOURNAL OF MATERIALS CHEMISTRY C, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 4, no. 17, 7 May 2016 (2016-05-07), GB , pages 3798 - 3808, XP055950153, ISSN: 2050-7526, DOI: 10.1039/C5TC03501E
HUANG JIACHEN, YANG JIE, SUN HUILIANG, FENG KUI, LIAO QIAOGAN, LI BOLIN, YAN HE, GUO XUGANG: "Material Enabling 20% Efficiency Inverted Perovskite Solar Cells †", CHINESE JOURNAL OF CHEMISTRY, ZHONGGUO KEXUEYUAN, CN, vol. 39, no. 6, 1 June 2021 (2021-06-01), CN , pages 1545 - 1552, XP055950155, ISSN: 1001-604X, DOI: 10.1002/cjoc.202100022
YAO PEIGEN, WANG YIXUAN, QIAO WEIGUO, SUN XIANGLANG, PENG HAIYAN, XIE XIAOLIN, LI ZHONG'AN: "Insights into molecular packing effects on the emission properties of fluorenone-based molecules in the aggregate state", JOURNAL OF MATERIALS CHEMISTRY C, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 9, no. 39, 14 October 2021 (2021-10-14), GB , pages 13687 - 13696, XP055950157, ISSN: 2050-7526, DOI: 10.1039/D1TC03459F
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, 2009, pages 6050 - 6051
SCIENCE, vol. 388, 2012, pages 643 - 647
CHEM. SCI., vol. 10, 2019, pages 6748 - 6769
YU XINYU, LI ZHEN, SUN XIANGLANG, ZHONG CHENG, ZHU ZONGLONG, LI ZHONG’AN, JEN ALEX K.-Y.: "Dopant-free dicyanofluoranthene-based hole transporting material with low cost enables efficient flexible perovskite solar cells", NANO ENERGY, ELSEVIER, NL, vol. 82, 1 April 2021 (2021-04-01), NL , pages 105701, XP055950150, ISSN: 2211-2855, DOI: 10.1016/j.nanoen.2020.105701
GAO, Z.Q. ; XIA, P.F. ; LO, P.K. ; MI, B.X. ; TAM, H.L. ; WONG, M.S. ; CHEAH, K.W. ; CHEN, C.H.: "p-Doped p-phenylenediamine-substituted fluorenes for organic electroluminescent devices", ORGANIC ELECTRONICS, ELSEVIER, AMSTERDAM, NL, vol. 10, no. 4, 1 July 2009 (2009-07-01), AMSTERDAM, NL, pages 666 - 673, XP026119399, ISSN: 1566-1199, DOI: 10.1016/j.orgel.2009.02.025
ZHONG HU; VEDBAR S. KHADKA; WEI WANG; DAVID W. GALIPEAU; XINGZHONG YAN: "Theoretical study of two-photon absorption properties and up-conversion efficiency of new symmetric organic π-conjugated molecules for photovoltaic devices", JOURNAL OF MOLECULAR MODELING, SPRINGER, DE, vol. 18, no. 8, 23 February 2012 (2012-02-23), DE , pages 3657 - 3667, XP035091276, ISSN: 0948-5023, DOI: 10.1007/s00894-012-1378-3
WIELOPOLSKI MATEUSZ, MARSZALEK MAGDALENA, BRUNETTI FULVIO G., JOLY DAMIEN, CALBO JOAQUÍN, ARAGÓ JUAN, MOSER JACQUES-E., HUMPHRY-BA: "Synthesis and optoelectronic properties of chemically modified bi-fluorenylidenes", JOURNAL OF MATERIALS CHEMISTRY C, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 4, no. 17, 7 May 2016 (2016-05-07), GB , pages 3798 - 3808, XP055950153, ISSN: 2050-7526, DOI: 10.1039/C5TC03501E
HUANG JIACHEN, YANG JIE, SUN HUILIANG, FENG KUI, LIAO QIAOGAN, LI BOLIN, YAN HE, GUO XUGANG: "Material Enabling 20% Efficiency Inverted Perovskite Solar Cells †", CHINESE JOURNAL OF CHEMISTRY, ZHONGGUO KEXUEYUAN, CN, vol. 39, no. 6, 1 June 2021 (2021-06-01), CN , pages 1545 - 1552, XP055950155, ISSN: 1001-604X, DOI: 10.1002/cjoc.202100022
YAO PEIGEN, WANG YIXUAN, QIAO WEIGUO, SUN XIANGLANG, PENG HAIYAN, XIE XIAOLIN, LI ZHONG'AN: "Insights into molecular packing effects on the emission properties of fluorenone-based molecules in the aggregate state", JOURNAL OF MATERIALS CHEMISTRY C, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 9, no. 39, 14 October 2021 (2021-10-14), GB , pages 13687 - 13696, XP055950157, ISSN: 2050-7526, DOI: 10.1039/D1TC03459F
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, 2009, pages 6050 - 6051
SCIENCE, vol. 388, 2012, pages 643 - 647
CHEM. SCI., vol. 10, 2019, pages 6748 - 6769
Attorney, Agent or Firm:
SHOWA INTERNATIONAL PATENT FIRM (JP)
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