Synthesis, characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer

Itaru Osaka, Masafumi Shimawaki, Hiroki Mori, Iori Doi, Eigo Miyazaki, Tomoyuki Koganezawa, Kazuo Takimiya

Research output: Contribution to journalArticle

237 Citations (Scopus)

Abstract

We report the synthesis and characterization of a novel donor-acceptor semiconducting polymer bearing naphthobisthiadiazole (NTz), a doubly benzothiadiazole (BTz)-fused ring, and its applications to organic field-effect transistors and bulk heterojunction solar cells. With NTz's highly π-extended structure and strong electron affinity, the NTz-based polymer (PNTz4T) affords a smaller bandgap and a deeper HOMO level than the BTz-based polymer (PBTz4T). PNTz4T exhibits not only high field-effect mobilities of ∼0.56 cm 2/(V s) but also high photovoltaic properties with power conversion efficiencies of ∼6.3%, both of which are significantly high compared to those for PBTz4T. This is most likely due to the more suitable electronic properties and, importantly, the more highly ordered structure of PNTz4T in the thin film than that of PBTz4T, which might originate in the different symmetry between the cores. NTz, with centrosymmetry, can lead to a more linear backbone in the present polymer system than BTz with axisymmetry, which might be favorable for better molecular ordering. These results demonstrate great promise for using NTz as a bulding unit for high-performance semiconducting polymers for both transistors and solar cells.

Original languageEnglish
Pages (from-to)3498-3507
Number of pages10
JournalJournal of the American Chemical Society
Volume134
Issue number7
DOIs
Publication statusPublished - Feb 22 2012
Externally publishedYes

Fingerprint

Semiconducting polymers
Solar cells
Polymers
Transistors
Bearings (structural)
Organic field effect transistors
Electron affinity
Electronic properties
Conversion efficiency
Heterojunctions
Energy gap
Thin films
benzo-1,2,3-thiadiazole
Electrons

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Synthesis, characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer. / Osaka, Itaru; Shimawaki, Masafumi; Mori, Hiroki; Doi, Iori; Miyazaki, Eigo; Koganezawa, Tomoyuki; Takimiya, Kazuo.

In: Journal of the American Chemical Society, Vol. 134, No. 7, 22.02.2012, p. 3498-3507.

Research output: Contribution to journalArticle

Osaka, Itaru ; Shimawaki, Masafumi ; Mori, Hiroki ; Doi, Iori ; Miyazaki, Eigo ; Koganezawa, Tomoyuki ; Takimiya, Kazuo. / Synthesis, characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 7. pp. 3498-3507.
@article{c2dcd0d178564c9d97dcce4c8bf794ba,
title = "Synthesis, characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer",
abstract = "We report the synthesis and characterization of a novel donor-acceptor semiconducting polymer bearing naphthobisthiadiazole (NTz), a doubly benzothiadiazole (BTz)-fused ring, and its applications to organic field-effect transistors and bulk heterojunction solar cells. With NTz's highly π-extended structure and strong electron affinity, the NTz-based polymer (PNTz4T) affords a smaller bandgap and a deeper HOMO level than the BTz-based polymer (PBTz4T). PNTz4T exhibits not only high field-effect mobilities of ∼0.56 cm 2/(V s) but also high photovoltaic properties with power conversion efficiencies of ∼6.3{\%}, both of which are significantly high compared to those for PBTz4T. This is most likely due to the more suitable electronic properties and, importantly, the more highly ordered structure of PNTz4T in the thin film than that of PBTz4T, which might originate in the different symmetry between the cores. NTz, with centrosymmetry, can lead to a more linear backbone in the present polymer system than BTz with axisymmetry, which might be favorable for better molecular ordering. These results demonstrate great promise for using NTz as a bulding unit for high-performance semiconducting polymers for both transistors and solar cells.",
author = "Itaru Osaka and Masafumi Shimawaki and Hiroki Mori and Iori Doi and Eigo Miyazaki and Tomoyuki Koganezawa and Kazuo Takimiya",
year = "2012",
month = "2",
day = "22",
doi = "10.1021/ja210687r",
language = "English",
volume = "134",
pages = "3498--3507",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "7",

}

TY - JOUR

T1 - Synthesis, characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based semiconducting polymer

AU - Osaka, Itaru

AU - Shimawaki, Masafumi

AU - Mori, Hiroki

AU - Doi, Iori

AU - Miyazaki, Eigo

AU - Koganezawa, Tomoyuki

AU - Takimiya, Kazuo

PY - 2012/2/22

Y1 - 2012/2/22

N2 - We report the synthesis and characterization of a novel donor-acceptor semiconducting polymer bearing naphthobisthiadiazole (NTz), a doubly benzothiadiazole (BTz)-fused ring, and its applications to organic field-effect transistors and bulk heterojunction solar cells. With NTz's highly π-extended structure and strong electron affinity, the NTz-based polymer (PNTz4T) affords a smaller bandgap and a deeper HOMO level than the BTz-based polymer (PBTz4T). PNTz4T exhibits not only high field-effect mobilities of ∼0.56 cm 2/(V s) but also high photovoltaic properties with power conversion efficiencies of ∼6.3%, both of which are significantly high compared to those for PBTz4T. This is most likely due to the more suitable electronic properties and, importantly, the more highly ordered structure of PNTz4T in the thin film than that of PBTz4T, which might originate in the different symmetry between the cores. NTz, with centrosymmetry, can lead to a more linear backbone in the present polymer system than BTz with axisymmetry, which might be favorable for better molecular ordering. These results demonstrate great promise for using NTz as a bulding unit for high-performance semiconducting polymers for both transistors and solar cells.

AB - We report the synthesis and characterization of a novel donor-acceptor semiconducting polymer bearing naphthobisthiadiazole (NTz), a doubly benzothiadiazole (BTz)-fused ring, and its applications to organic field-effect transistors and bulk heterojunction solar cells. With NTz's highly π-extended structure and strong electron affinity, the NTz-based polymer (PNTz4T) affords a smaller bandgap and a deeper HOMO level than the BTz-based polymer (PBTz4T). PNTz4T exhibits not only high field-effect mobilities of ∼0.56 cm 2/(V s) but also high photovoltaic properties with power conversion efficiencies of ∼6.3%, both of which are significantly high compared to those for PBTz4T. This is most likely due to the more suitable electronic properties and, importantly, the more highly ordered structure of PNTz4T in the thin film than that of PBTz4T, which might originate in the different symmetry between the cores. NTz, with centrosymmetry, can lead to a more linear backbone in the present polymer system than BTz with axisymmetry, which might be favorable for better molecular ordering. These results demonstrate great promise for using NTz as a bulding unit for high-performance semiconducting polymers for both transistors and solar cells.

UR - http://www.scopus.com/inward/record.url?scp=84857424718&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84857424718&partnerID=8YFLogxK

U2 - 10.1021/ja210687r

DO - 10.1021/ja210687r

M3 - Article

C2 - 22280564

AN - SCOPUS:84857424718

VL - 134

SP - 3498

EP - 3507

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 7

ER -