Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs)

Jangdae Youn; Sureshraju Vegiraju; Jonathan D. Emery; Benjamin J. Leever; Sumit Kewalramani; Silvia J. Lou; Shiming Zhang; Kumaresan Prabakaran; Yamuna Ezhumalai; Choongik Kim; Peng Yi Huang; Charlotte Stern; Wen Chung Chang; Michael J. Bedzyk; Lin X. Chen; Ming Chou Chen; Antonio Facchetti; Tobin J. Marks

doi:10.1002/aelm.201500098

Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs)

Jangdae Youn, Sureshraju Vegiraju, Jonathan D. Emery, Benjamin J. Leever, Sumit Kewalramani, Silvia J. Lou, Shiming Zhang, Kumaresan Prabakaran, Yamuna Ezhumalai, Choongik Kim^*, Peng Yi Huang, Charlotte Stern, Wen Chung Chang, Michael J. Bedzyk, Lin X. Chen, Ming Chou Chen, Antonio Facchetti, Tobin J. Marks

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

46 Scopus citations

Abstract

Three new fused thiophene semiconductors, end-capped with diperfluorophenylthien-2-yl (DFPT) groups (DFPT-thieno[2′,3′:4,5]thieno[3,2-b]thieno[2,3-d]thiophene (TTA), DFPT-dithieno[2,3-b:3′,2′-d]thiophenes (DTT), and DFPT-thieno[3,2-b]thiophene (TT)), are synthesized and characterized in organic thin film transistors. Good environmental stability of the newly developed materials is demonstrated via thermal analysis as well as degradation tests under white light. The molecular structures of all three perfluorophenylthien-2-yl end-functionalized derivatives are determined by single crystal X-ray diffraction. DFPT-TTA and DFPT-TT exhibit good n-type TFT performance, with mobilities up to 0.43 and 0.33 cm² V⁻¹ s⁻¹, respectively. These are among the best performing n-type materials of all fused thiophenes reported to date. The best thin film transistor device performance is achieved via an n-octadecyltrichlorosilane dielectric surface treatment on the thermally grown Si/SiO₂ substrates prior to vapor-phase semiconductor deposition. Within the DFPT series, carrier mobility magnitudes depend strongly on the semiconductor growth conditions and the gate dielectric surface treatment.

Original language	English (US)
Article number	1500098
Journal	Advanced Electronic Materials
Volume	1
Issue number	8
DOIs	https://doi.org/10.1002/aelm.201500098
State	Published - Aug 2015

Funding

J.Y. and S.V. contributed equally to this work. This research was supported by the NSF MRSEC program (Grant No. DMR-1121262) at the Materials Research Center of Northwestern U., by AFOSR Grant No. FA9550-08-1-0331, by the National Science Council, Taiwan, Republic of China (Grant Nos. NSC102-2923-M-008-004-MY2 and MOST 103-2113-M-008-004), and by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (NRF-2014R1A1A1A05002158) and by the Center for Advanced Soft Electronics under the Global Frontier Research Program of the Ministry of Science, ICT and Future Planning (Code No. 2013M3A6A5073175). Use of the Advanced Photon Source, 33BM-C, was supported by the U.S. DOE, Office of Science, Office of Basic Energy Sciences, under Contract No. DE-AC02-06CH11357. This work made use of the J. B. Cohen X-ray Diffraction Facility.

Keywords

dithienothiophenes (DTTs)
fused thiophenes
organic semiconductors
organic thin film transistors (OTFTs)
perfluorophenyl
tetrathienoacens (TTAs)
thienothiophenes (TTs)

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials

Access to Document

10.1002/aelm.201500098

Cite this

Youn, J., Vegiraju, S., Emery, J. D., Leever, B. J., Kewalramani, S., Lou, S. J., Zhang, S., Prabakaran, K., Ezhumalai, Y., Kim, C., Huang, P. Y., Stern, C., Chang, W. C., Bedzyk, M. J., Chen, L. X., Chen, M. C., Facchetti, A., & Marks, T. J. (2015). Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs). Advanced Electronic Materials, 1(8), Article 1500098. https://doi.org/10.1002/aelm.201500098

@article{685d0632437445bf9b763d32e4778046,

title = "Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs)",

abstract = "Three new fused thiophene semiconductors, end-capped with diperfluorophenylthien-2-yl (DFPT) groups (DFPT-thieno[2′,3′:4,5]thieno[3,2-b]thieno[2,3-d]thiophene (TTA), DFPT-dithieno[2,3-b:3′,2′-d]thiophenes (DTT), and DFPT-thieno[3,2-b]thiophene (TT)), are synthesized and characterized in organic thin film transistors. Good environmental stability of the newly developed materials is demonstrated via thermal analysis as well as degradation tests under white light. The molecular structures of all three perfluorophenylthien-2-yl end-functionalized derivatives are determined by single crystal X-ray diffraction. DFPT-TTA and DFPT-TT exhibit good n-type TFT performance, with mobilities up to 0.43 and 0.33 cm2 V−1 s−1, respectively. These are among the best performing n-type materials of all fused thiophenes reported to date. The best thin film transistor device performance is achieved via an n-octadecyltrichlorosilane dielectric surface treatment on the thermally grown Si/SiO2 substrates prior to vapor-phase semiconductor deposition. Within the DFPT series, carrier mobility magnitudes depend strongly on the semiconductor growth conditions and the gate dielectric surface treatment.",

keywords = "dithienothiophenes (DTTs), fused thiophenes, organic semiconductors, organic thin film transistors (OTFTs), perfluorophenyl, tetrathienoacens (TTAs), thienothiophenes (TTs)",

author = "Jangdae Youn and Sureshraju Vegiraju and Emery, {Jonathan D.} and Leever, {Benjamin J.} and Sumit Kewalramani and Lou, {Silvia J.} and Shiming Zhang and Kumaresan Prabakaran and Yamuna Ezhumalai and Choongik Kim and Huang, {Peng Yi} and Charlotte Stern and Chang, {Wen Chung} and Bedzyk, {Michael J.} and Chen, {Lin X.} and Chen, {Ming Chou} and Antonio Facchetti and Marks, {Tobin J.}",

note = "Funding Information: J.Y. and S.V. contributed equally to this work. This research was supported by the NSF MRSEC program (Grant No. DMR-1121262) at the Materials Research Center of Northwestern U., by AFOSR Grant No. FA9550-08-1-0331, by the National Science Council, Taiwan, Republic of China (Grant Nos. NSC102-2923-M-008-004-MY2 and MOST 103-2113-M-008-004), and by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (NRF-2014R1A1A1A05002158) and by the Center for Advanced Soft Electronics under the Global Frontier Research Program of the Ministry of Science, ICT and Future Planning (Code No. 2013M3A6A5073175). Use of the Advanced Photon Source, 33BM-C, was supported by the U.S. DOE, Office of Science, Office of Basic Energy Sciences, under Contract No. DE-AC02-06CH11357. This work made use of the J. B. Cohen X-ray Diffraction Facility. Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2015",

month = aug,

doi = "10.1002/aelm.201500098",

language = "English (US)",

volume = "1",

journal = "Advanced Electronic Materials",

issn = "2199-160X",

publisher = "Wiley-VCH Verlag",

number = "8",

}

Youn, J, Vegiraju, S, Emery, JD, Leever, BJ, Kewalramani, S, Lou, SJ, Zhang, S, Prabakaran, K, Ezhumalai, Y, Kim, C, Huang, PY, Stern, C, Chang, WC, Bedzyk, MJ , Chen, LX, Chen, MC, Facchetti, A & Marks, TJ 2015, 'Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs)', Advanced Electronic Materials, vol. 1, no. 8, 1500098. https://doi.org/10.1002/aelm.201500098

TY - JOUR

T1 - Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs)

AU - Youn, Jangdae

AU - Vegiraju, Sureshraju

AU - Emery, Jonathan D.

AU - Leever, Benjamin J.

AU - Kewalramani, Sumit

AU - Lou, Silvia J.

AU - Zhang, Shiming

AU - Prabakaran, Kumaresan

AU - Ezhumalai, Yamuna

AU - Kim, Choongik

AU - Huang, Peng Yi

AU - Stern, Charlotte

AU - Chang, Wen Chung

AU - Bedzyk, Michael J.

AU - Chen, Lin X.

AU - Chen, Ming Chou

AU - Facchetti, Antonio

AU - Marks, Tobin J.

N1 - Funding Information: J.Y. and S.V. contributed equally to this work. This research was supported by the NSF MRSEC program (Grant No. DMR-1121262) at the Materials Research Center of Northwestern U., by AFOSR Grant No. FA9550-08-1-0331, by the National Science Council, Taiwan, Republic of China (Grant Nos. NSC102-2923-M-008-004-MY2 and MOST 103-2113-M-008-004), and by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (NRF-2014R1A1A1A05002158) and by the Center for Advanced Soft Electronics under the Global Frontier Research Program of the Ministry of Science, ICT and Future Planning (Code No. 2013M3A6A5073175). Use of the Advanced Photon Source, 33BM-C, was supported by the U.S. DOE, Office of Science, Office of Basic Energy Sciences, under Contract No. DE-AC02-06CH11357. This work made use of the J. B. Cohen X-ray Diffraction Facility. Publisher Copyright: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2015/8

Y1 - 2015/8

N2 - Three new fused thiophene semiconductors, end-capped with diperfluorophenylthien-2-yl (DFPT) groups (DFPT-thieno[2′,3′:4,5]thieno[3,2-b]thieno[2,3-d]thiophene (TTA), DFPT-dithieno[2,3-b:3′,2′-d]thiophenes (DTT), and DFPT-thieno[3,2-b]thiophene (TT)), are synthesized and characterized in organic thin film transistors. Good environmental stability of the newly developed materials is demonstrated via thermal analysis as well as degradation tests under white light. The molecular structures of all three perfluorophenylthien-2-yl end-functionalized derivatives are determined by single crystal X-ray diffraction. DFPT-TTA and DFPT-TT exhibit good n-type TFT performance, with mobilities up to 0.43 and 0.33 cm2 V−1 s−1, respectively. These are among the best performing n-type materials of all fused thiophenes reported to date. The best thin film transistor device performance is achieved via an n-octadecyltrichlorosilane dielectric surface treatment on the thermally grown Si/SiO2 substrates prior to vapor-phase semiconductor deposition. Within the DFPT series, carrier mobility magnitudes depend strongly on the semiconductor growth conditions and the gate dielectric surface treatment.

AB - Three new fused thiophene semiconductors, end-capped with diperfluorophenylthien-2-yl (DFPT) groups (DFPT-thieno[2′,3′:4,5]thieno[3,2-b]thieno[2,3-d]thiophene (TTA), DFPT-dithieno[2,3-b:3′,2′-d]thiophenes (DTT), and DFPT-thieno[3,2-b]thiophene (TT)), are synthesized and characterized in organic thin film transistors. Good environmental stability of the newly developed materials is demonstrated via thermal analysis as well as degradation tests under white light. The molecular structures of all three perfluorophenylthien-2-yl end-functionalized derivatives are determined by single crystal X-ray diffraction. DFPT-TTA and DFPT-TT exhibit good n-type TFT performance, with mobilities up to 0.43 and 0.33 cm2 V−1 s−1, respectively. These are among the best performing n-type materials of all fused thiophenes reported to date. The best thin film transistor device performance is achieved via an n-octadecyltrichlorosilane dielectric surface treatment on the thermally grown Si/SiO2 substrates prior to vapor-phase semiconductor deposition. Within the DFPT series, carrier mobility magnitudes depend strongly on the semiconductor growth conditions and the gate dielectric surface treatment.

KW - dithienothiophenes (DTTs)

KW - fused thiophenes

KW - organic semiconductors

KW - organic thin film transistors (OTFTs)

KW - perfluorophenyl

KW - tetrathienoacens (TTAs)

KW - thienothiophenes (TTs)

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UR - http://www.scopus.com/inward/citedby.url?scp=84952815817&partnerID=8YFLogxK

U2 - 10.1002/aelm.201500098

DO - 10.1002/aelm.201500098

M3 - Article

AN - SCOPUS:84952815817

SN - 2199-160X

VL - 1

JO - Advanced Electronic Materials

JF - Advanced Electronic Materials

IS - 8

M1 - 1500098

ER -

Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs)

Abstract

Funding

Keywords

ASJC Scopus subject areas

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CCDC 1043766: Experimental Crystal Structure Determination

CCDC 1043765: Experimental Crystal Structure Determination

CCDC 1043764: Experimental Crystal Structure Determination

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Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs)

Abstract

Funding

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1043766: Experimental Crystal Structure Determination

CCDC 1043765: Experimental Crystal Structure Determination

CCDC 1043764: Experimental Crystal Structure Determination

Cite this