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DOI: 10.1055/s-0030-1261191
First Tetrabutylanthradithiophene (TBADT) Derivatives for Solution-Processed Thin-Film Transistors
Publication History
Publication Date:
24 August 2011 (online)

Abstract
Three new solution-processable tetrabutylanthradithiophene (TBADT)-based organic semiconductors bearing two phenylethynyl, thiophen-2-ylethynyl, and thieno[3,2-b]thiophen-5-ylethynyl substituents have been synthesized and their thermal, optical, and electrochemical properties have been characterized. Preliminary tests of these compounds via drop-casting for thin-film transistors showed p-channel TFT transport with hole mobilities as high as 1.510-³ cm²/Vs and with a current on/off ratio of 104.
Key words
organic semiconductor - organic thin-film transistor - anthradithiophene - solution process - pentacene
- Supporting Information for this article is available online:
- Supporting Information (PDF)
- 1a
Arias AC.MacKenzie JD.McCulloch I.Rivnay J.Salleo A. Chem. Rev. 2010, 110: 3Reference Ris Wihthout Link - 1b
Di C A.Liu Y.Yungi Y.Gui Z.Zhu D. Acc. Chem. Res. 2009, 42: 1573Reference Ris Wihthout Link - 1c
Chabinyc M.Loo Y.-L. J. Macromol. Sci. Polym. Rev. 2006, 46: 1Reference Ris Wihthout Link - 1d
Dodabalapur A. Nature (London) 2005, 434: 151Reference Ris Wihthout Link - 1e
Sirringhaus H. Adv. Mater. 2005, 17: 2411Reference Ris Wihthout Link - 2a
Gao X.Di C.Hu Y.Yang X.Fan H.Zhang F.Liu Y.Li H.Zhu D. J. Am. Chem. Soc. 2010, 132: 3697Reference Ris Wihthout Link - 2b
Kim C.Chen M.-C.Chiang Y.-J.Guo Y.-J.Youn J.Huang H.Liang Y.-J.Lin Y.-J.Huang Y.-W.Hu T.-S.Lee G.-H.Facchetti A.Marks TJ. Org. Electron. 2010, 11: 801Reference Ris Wihthout Link - 2c
Pal BN.Dhar BM.See KC.Katz HE. Nat. Mater. 2010, 9: 279Reference Ris Wihthout Link - 2d
Beverina L.Salice P. Eur. J. Org. Chem. 2010, 7: 1207Reference Ris Wihthout Link - 2e
Yan H.Chen Z.Zheng Y.Newman CE.Quinn JR.Dolz F.Kastler M.Facchetti A. Nature (London) 2009, 457: 679Reference Ris Wihthout Link - 2f
Cheng X.Noh Y.-Y.Wang J.Tello M.Frisch J.Blum R.-P.Vollmer A.Rabe JP.Koch N.Sirringhaus H. Adv. Funct. Mater. 2009, 19: 2407Reference Ris Wihthout Link - 2g
Reese C.Roberts ME.Parkin SR.Bao Z. Adv. Mater. 2009, 21: 3678Reference Ris Wihthout Link - 2h
Kim C.Facchetti A.Marks TJ. Science 2007, 318: 76Reference Ris Wihthout Link - 3a
Park SK.Mourey DA.Han J.-I.Anthony JE.Jackson TN. Org. Electron. 2009, 10: 486Reference Ris Wihthout Link - 3b
Kelly TW.Baude PF.Gerlach C.Ender DE.Muyres D.Hasse MA.Vogel DE.Theiss SD. Chem. Mater. 2004, 16: 4413Reference Ris Wihthout Link - 3c
Payne MM.Parkin SR.Anthony JE. J. Am. Chem. Soc. 2005, 127: 8028Reference Ris Wihthout Link - 3d
Gundlach DJ.Lin YY.Jackson TN.Nelson SF. Appl. Phys. Lett. 2002, 80: 2925Reference Ris Wihthout Link - 3e
Meng H.Bendikov M.Mitchell G.Helgeson R.Wudl F.Bao Z.Siegrist T.Kloc C.Chen CH. Adv. Mater. 2003, 15: 1090Reference Ris Wihthout Link - 4a
Laquindanum JG.Katz HE.Lovinger AJ. J. Am. Chem. Soc. 1998, 120: 664Reference Ris Wihthout Link - 4b
Payne MM.Odom SA.Parkin SR.Anthony JE. Org. Lett. 2004, 6: 3325Reference Ris Wihthout Link - 4c
Jurchescu OD.Subramanian S.Kline RJ.Hudson SD.Anthony JE.Jackson TN.Gundlach DJ. Chem. Mater. 2008, 20: 6733Reference Ris Wihthout Link - 4d
Chen M.-C.Kim C.Chen S.-Y.Chiang Y.-J.Chung M.-C.Facchetti A.Marks TJ. J. Mater. Chem. 2008, 18: 1029Reference Ris Wihthout Link - 5a
Youn J.Chen M.-C.Liang Y.-J.Huang H.Ortiz RP.Kim C.Stern C.Hu T.-S.Chen L.-H.Yan J.-Y.Facchetti A.Marks TJ. Chem. Mater. 2010, 22: 5031Reference Ris Wihthout Link - 5b
Mauldin CE.Puntambekar K.Murphy AR.Liao F.Subramanian V.Frechet JMJ.Delongchamp DM.Fischer DA.Toney MF. Chem. Mater. 2009, 21: 1927Reference Ris Wihthout Link - 5c
Chen M.-C.Chiang Y.-J.Kim C.Guo Y.-J.Chen S.-Y.Liang Y.-J.Huang Y.-W.Hu T.-S.Lee G.-H.Facchetti A.Marks TJ. Chem. Commun. 2009, 1846Reference Ris Wihthout Link - 5d
Takimiya K.Kunugi Y.Konda Y.Ebata H.Toyoshima Y.Otsubo T. J. Am. Chem. Soc. 2006, 128: 3044Reference Ris Wihthout Link - 5e
Xiao K.Liu Y.Qi T.Zhang W.Wang F.Gao J.Qiu W.Ma Y.Cui G.Chen S.Zhan X.Yu G.Qin J.Hu W.Zhu D. J. Am. Chem. Soc. 2005, 127: 13281Reference Ris Wihthout Link - 5f
Ando S.Nishida J.Tada H.Inoue Y.Tokito S.Yamashita Y. J. Am. Chem. Soc. 2005, 127: 5336Reference Ris Wihthout Link - For example, the C-6/C-13 positions of pentacene are sensitive to oxygen in solution when exposed to visible light in air, see:
- 6a
Wolak MA.Jang BB.Palilis LC.Kafafi ZH. J. Phys. Chem. B 2004, 108: 5492Reference Ris Wihthout Link - 6b
Reddy AR.Bendikov M. Chem. Commun. 2006, 1179Reference Ris Wihthout Link - 7a
Anthony JE.Brooks JS.Eaton DL.Parkin SR. J. Am. Chem. Soc. 2001, 123: 9482Reference Ris Wihthout Link - 7b
Sheraw CD.Jackson TN.Eaton DL.Anthony JE. Adv. Mater. 2003, 15: 2009Reference Ris Wihthout Link - 7c
Li Y.Wu Y.Liu P.Prostran Z.Gardner S.Ong BS. Chem. Mater. 2007, 19: 418Reference Ris Wihthout Link - 7d
Benard CP.Geng Z.Heuft MA.VanCrey K.Fallis AG. J. Org. Chem. 2007, 72: 7229Reference Ris Wihthout Link - 7e
Lehnherr D.McDonald R.Tykwinski RR. Org. Lett. 2008, 10: 4163Reference Ris Wihthout Link - 8a
Payne MM.Parkin SR.Anthony JE.Kuo C.-C.Jackson TN. J. Am. Chem. Soc. 2005, 127: 4986Reference Ris Wihthout Link - 8b
Subramanian S.Park SK.Parkin SR.Podzorov V.Jackson TN.Anthony JE. J. Am. Chem. Soc. 2008, 130: 2706Reference Ris Wihthout Link - 9
Kim C.Huang P.-Y.Jhuang J.-W.Chen M.-C.Ho J.-C.Hu T.-S.Yan J.-Y.Chen L.-H.Lee G.-H.Facchetti A.Marks TJ. Org. Electron. 2010, 11: 1363 - 10
Anthony JE. Chem. Rev. 2006, 106: 5028 - 12
Reinecke MG.Adickes HW.Pyun C. J. Org. Chem. 1971, 36: 2690 - 13
Zhao C.Zhang Y.Ng M.-K. J. Org. Chem. 2007, 72: 6364 - 14
Corey EJ.Fuchs PL. Tetrahedron Lett. 1972, 4831 - 15
Beny JP.Dhawan SN.Kagan J.Sundlass S. J. Org. Chem. 1982, 11: 2201 - 16 The endotherm was not observed in
the second run of DSC measurement. After performing the second run
(samples were heated above the decomposition temperature), the residues
in the DSC cell were monitored by ¹H NMR and were
found to be different from the starting ADT. In addition to the
color change, the solubility of these ADT (residues) was also dramatically
decreased. Since there was no weight loss from TGA, dimerization
of the ADT is suspected, see:
Coppo P.Yeates SG. Adv. Mater. 2005, 17: 3001 - 17
Maliakal A.Raghavachari K.Katz HE.Chandross E.Siegrist T. Chem. Mater. 2004, 16: 4980 - 18 It has been reported that alkynyl
substitution lowers the LUMO energy for pentacene derivatives as
compared to that of unsubstituted pentacene, which hinders their photooxidation.
See:
Akhtaruzzaman M.Kamata N.Nishida J.Ando S.Tada H.Tomura M.Yamashita Y. Chem. Commun. 2005, 3183 ; see also ref. 7c - 19
Yamada H.Yamashita Y.Kikuchi M.Watanabe H.Okujima T.Uno H.Ogawa T.Ohara K.Ono N. Chem. Eur. J. 2005, 11: 6212 - 20 Measured with a Pt working electrode
in an o-dichloro-benzene solution using
0.1 mol dm-³ Bu4NPF6 as
the supporting electrolyte. See:
Naraso Nishida J.Kumaki D.Tokito S.Yamashita Y. J. Am. Chem. Soc. 2006, 128: 9598 - 21 Similar trends are reported in:
Wang J.Liu K.Liu Y.-Y.Song C.-L.Shi Z.-F.Peng J.-B.Zhang H.-L.Cao X.-P. Org. Lett. 2009, 11: 2563
References and Notes
Since three new TBADT derivatives are very soluble in common solvents, no crystal structures were obtained. Thus, the elucidation of interrelationships between molecular structure and the characterization of organic thin-film transistors are not available so far.
22The solubility of TBADT derivatives
was ca. 20 (for 3)
to 40 (for 1 and 2) mg/mL
in CHCl3.