Title:
TETRACENE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/078217
Kind Code:
A1
Abstract:
Disclosed are a 2,8-disubstituted tetracene derivative represented by formula (I), a preparation method therefor, and the use thereof. The compound can be used for preparing an organic semiconductor device, particularly an organic field-effect transistor (OFET). A single crystal and a thin-film device, as prepared from the above-mentioned tetracene derivative, have a higher mobility, threshold voltage and switch ratio. The preparation method is simple, can greatly increase the yield of 2,8-dibromotetracene, reduces the number of post-treatment steps of intermediates, increases the synthetic efficiency, reduces the preparation time, and has a relatively low cost. The total yield of the synthesis route reaches approximately 50%. The present invention is very suitable for scaled-up preparation in a laboratory, and can provide sufficient raw materials for the preparation of a photoelectronic device containing the tetracene derivative.
Inventors:
HU WENPING (CN)
SHU ZHIBIN (CN)
DONG HUANLI (CN)
WANG PU (CN)
SHU ZHIBIN (CN)
DONG HUANLI (CN)
WANG PU (CN)
Application Number:
PCT/CN2020/123012
Publication Date:
April 29, 2021
Filing Date:
October 22, 2020
Export Citation:
Assignee:
INST CHEMISTRY CAS (CN)
International Classes:
C07C15/38; C07C25/22; C07D405/10; C07D409/10; C07D417/10; H01L51/30; H01L51/54
Domestic Patent References:
| WO2019150988A1 | 2019-08-08 | |||
| WO2009028460A1 | 2009-03-05 |
Foreign References:
| JP2006028054A | 2006-02-02 | |||
| JP2006028055A | 2006-02-02 | |||
| CN102718741A | 2012-10-10 | |||
| CN103145524A | 2013-06-12 |
Other References:
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OMACHI HARUKA, SEGAWA YASUTOMO, ITAMI KENICHIRO: "Synthesis and Racemization Process of Chiral Carbon Nanorings: A Step toward the Chemical Synthesis of Chiral Carbon Nanotubes", ORGANIC LETTERS ., AMERICAN CHEMICAL SOCIETY, US, vol. 13, no. 9, 6 May 2011 (2011-05-06), US, pages 2480 - 2483, XP055805778, ISSN: 1523-7060, DOI: 10.1021/ol200730m
HOU, LIMEI ET AL.: "Theoretical Study on Electronic Structure and Photophysical Properties of 2,6-dithienyl Acene Oligomers", JOURNAL OF HUAIYIN TEACHERS COLLEGE(NATURAL SCIENCE EDITION), vol. 8, no. 2, 30 June 2009 (2009-06-30), pages 148 - 153, XP055805811, ISSN: 1671-6876
KIMOTO TAKAKAZU, TANAKA KENRO, SAKAI YOSHIMASA, OHNO AKIRA, YOZA KENJI, KOBAYASHI KENJI: "2,8- and 2,9-Diboryltetracenes as Useful Building Blocks for Extended π-Conjugated Tetracenes", ORGANIC LETTERS ., AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 16, 20 August 2009 (2009-08-20), US, pages 3658 - 3661, XP055805824, ISSN: 1523-7060, DOI: 10.1021/ol901420p
LIU HONGMEI, YU CUI, GAO NENGYUE, ZHAO JIANWEI: "The Diversity of Electron-Transport Behaviors of Molecular Junctions: Correlation with the Electron-Transport Pathway", CHEMPHYSCHEM - A EUROPEAN JOURNAL OF CHEMICAL PHYSICS & PHYSICALCHEMISTRY., WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 11, 8 April 2010 (2010-04-08), DE, pages 1895 - 1902, XP055805831, ISSN: 1439-4235, DOI: 10.1002/cphc.201000092
SIMON WOODWARD, MIRIAM ACKERMANN, SAURABH K. AHIRWAR, LAURENCE BURROUGHS, MARY ROBERT GARRETT, JOHN RITCHIE, JONATHAN SHINE, BJ�RK: "Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, vol. 23, no. 32, 7 June 2017 (2017-06-07), pages 7819 - 7824, XP055436261, ISSN: 0947-6539, DOI: 10.1002/chem.201701170
OMACHI HARUKA, SEGAWA YASUTOMO, ITAMI KENICHIRO: "Synthesis and Racemization Process of Chiral Carbon Nanorings: A Step toward the Chemical Synthesis of Chiral Carbon Nanotubes", ORGANIC LETTERS ., AMERICAN CHEMICAL SOCIETY, US, vol. 13, no. 9, 6 May 2011 (2011-05-06), US, pages 2480 - 2483, XP055805778, ISSN: 1523-7060, DOI: 10.1021/ol200730m
HOU, LIMEI ET AL.: "Theoretical Study on Electronic Structure and Photophysical Properties of 2,6-dithienyl Acene Oligomers", JOURNAL OF HUAIYIN TEACHERS COLLEGE(NATURAL SCIENCE EDITION), vol. 8, no. 2, 30 June 2009 (2009-06-30), pages 148 - 153, XP055805811, ISSN: 1671-6876
KIMOTO TAKAKAZU, TANAKA KENRO, SAKAI YOSHIMASA, OHNO AKIRA, YOZA KENJI, KOBAYASHI KENJI: "2,8- and 2,9-Diboryltetracenes as Useful Building Blocks for Extended π-Conjugated Tetracenes", ORGANIC LETTERS ., AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 16, 20 August 2009 (2009-08-20), US, pages 3658 - 3661, XP055805824, ISSN: 1523-7060, DOI: 10.1021/ol901420p
LIU HONGMEI, YU CUI, GAO NENGYUE, ZHAO JIANWEI: "The Diversity of Electron-Transport Behaviors of Molecular Junctions: Correlation with the Electron-Transport Pathway", CHEMPHYSCHEM - A EUROPEAN JOURNAL OF CHEMICAL PHYSICS & PHYSICALCHEMISTRY., WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 11, 8 April 2010 (2010-04-08), DE, pages 1895 - 1902, XP055805831, ISSN: 1439-4235, DOI: 10.1002/cphc.201000092
SIMON WOODWARD, MIRIAM ACKERMANN, SAURABH K. AHIRWAR, LAURENCE BURROUGHS, MARY ROBERT GARRETT, JOHN RITCHIE, JONATHAN SHINE, BJ�RK: "Straightforward Synthesis of 2- and 2,8-Substituted Tetracenes", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, vol. 23, no. 32, 7 June 2017 (2017-06-07), pages 7819 - 7824, XP055436261, ISSN: 0947-6539, DOI: 10.1002/chem.201701170
Attorney, Agent or Firm:
BEIJING ORIGINTELLIGENCE IP LAW FIRM (CN)
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