[1]Benzothieno[3,2-b][1]benzothiophene-based liquid crystalline organic semiconductor for solution-processed organic thin film transistors

다국어 초록 (Multilingual Abstract)

Liquid crystalline organic semiconductors have drawn tremendous interest due to potentials of applicationsin organic thin-film transistors (OTFTs) with their high electrical performance and solutionprocessability.
However, alkylated liquid crystals often encounter poor thermal durability and mobilitydrop at smectic E (SmE) phase. Here, we introduce new solution-processable [1]benzothieno[3,2-b][1]benzothiophene-based small molecules with different types of alkyl side chains for OTFTs. All BTBT derivativesshowed smectic phase; dialkylated 2-octyl-7-(50-octyl-[2,20-bithiophen]-5-yl)benzo[b]benzo[4,5]thieno[2,3-d]thiophene (O-2Th-BTBT) and 2-(50-(2-ethylhexyl)-[2,20-bithiophen]-5-yl)-7-octylbenzo[b]benzo[4,5]thieno[2,3-d]thiophene (E-2Th-BTBT) suffered mobility degradation at SmE phase. However,monoalkylated 2-([2,20-bithiophen]-5-yl)-7-octylbenzo[b]benzo[4,5]thieno[2,3-d]thiophene (2Th-BTBT)did not exhibit SmE phase over temperature range, resulting in high carrier mobility up to 0.31 cm2/Vsthrough molecular bilayer transition by thermal annealing. Physicochemical and liquid crystal propertieswere analyzed, and thin film characterization by atomic force microscopy and X-ray diffraction wasdiscussed.

참고문헌 (Reference)

1 K.T. H. Junichi,

2 H. Iino, 647 : 37-, 2017

3 Gloria Zanotti, "[1]Benzothieno[3,2‐b][1]benzothiophene‐Phthalocyanine Derivatives: A Subclass of Solution‐Processable Electron‐Rich Hole Transport Materials" Wiley 85 (85): 2376-2386, 2020

4 Yusuke Tsutsui, "Unraveling Unprecedented Charge Carrier Mobility through Structure Property Relationship of Four Isomers of Didodecyl[1]benzothieno[3,2‐ b ][1]benzothiophene" Wiley 28 (28): 7106-7114, 2016

5 S. Lai, "Ultralow Voltage, OTFT-Based Sensor for Label-Free DNA Detection" Wiley 25 (25): 103-107, 2012

6 D. J. Gundlach, "Thin-film transistors based on well-ordered thermally evaporated naphthacene films" AIP Publishing 80 (80): 2925-2927, 2002

7 Kazuo Takimiya, "Thienoacene-Based Organic Semiconductors" Wiley 23 (23): 4347-4370, 2011

8 Claude Niebel, "Thienoacene dimers based on the thieno[3,2-b]thiophene moiety: synthesis, characterization and electronic properties" Royal Society of Chemistry (RSC) 3 (3): 674-685, 2015

9 Claude Niebel, "Thienoacene dimers based on the thieno[3,2-b]thiophene moiety: synthesis, characterization and electronic properties" Royal Society of Chemistry (RSC) 3 (3): 674-685, 2015

10 Motonori Watanabe, "The synthesis, crystal structure and charge-transport properties of hexacene" Springer Science and Business Media LLC 4 (4): 574-578, 2012

11 John F. Sebastian, "The electronic effects of alkyl groups" American Chemical Society (ACS) 48 (48): 97-, 1971

12 O. V. Borshchev, "Synthesis of organosilicon derivatives of [1]benzothieno[3,2-b][1]-benzothiophene for efficient monolayer Langmuir–Blodgett organic field effect transistors" Royal Society of Chemistry (RSC) 53 (53): 885-888, 2017

13 Sureshraju Vegiraju, "Synthesis and characterization of solution-processable diketopyrrolopyrrole (DPP) and tetrathienothiophene (TTA)-based small molecules for organic thin film transistors and organic photovoltaic cells" Elsevier BV 133 : 280-291, 2016

14 Kwanghee Cho, "Synthesis and characterization of fluorene derivatives as organic semiconductors for organic field-effect transistor" Informa UK Limited 690 (690): 56-66, 2019

15 Yongchul Lee, "Synthesis and characterization of benzo[b]thieno[2,3-d]thiophene (BTT) derivatives as solution-processable organic semiconductors for organic field-effect transistors" Elsevier BV 282 : 116944-, 2021

16 Y.-Y. Lin, "Stacked pentacene layer organic thin-film transistors with improved characteristics" Institute of Electrical and Electronics Engineers (IEEE) 18 (18): 606-608, 1997

17 Yuze Lin, "Small molecule semiconductors for high-efficiency organic photovoltaics" Royal Society of Chemistry (RSC) 41 (41): 4245-, 2012

18 Wen Shi, "Search for Organic Thermoelectric Materials with High Mobility: The Case of 2,7-Dialkyl[1]benzothieno[3,2-b][1]benzothiophene Derivatives" American Chemical Society (ACS) 26 (26): 2669-2677, 2014

19 Zhimin Chai, "Scalable Directed Assembly of Highly Crystalline 2,7-Dioctyl[1]benzothieno[3,2-b][1]benzothiophene (C8-BTBT) Films" American Chemical Society (ACS) 10 (10): 18123-18130, 2018

20 Gilles Horowitz, "Role of the semiconductor/insulator interface in the characteristics of π-conjugated-oligomer-based thin-film transistors" Elsevier BV 51 (51): 419-424, 1992

21 M. Dohr, "Reversibility of temperature driven discrete layer-by-layer formation of dioctyl-benzothieno-benzothiophene films" Royal Society of Chemistry (RSC) 13 (13): 2322-2329, 2017

22 Alexandra F. Paterson, "Recent Progress in High-Mobility Organic Transistors: A Reality Check" Wiley 30 (30): 1801079-, 2018

23 Congyan Lu, "Progress in flexible organic thin-film transistors and integrated circuits" Elsevier BV 61 (61): 1081-1096, 2016

24 V. Subramanian, "Printed organic transistors for ultra-low-cost RFID applications" Institute of Electrical and Electronics Engineers (IEEE) 28 (28): 742-747, 2005

25 C. D. Sheraw, "Organic thin-film transistor-driven polymer-dispersed liquid crystal displays on flexible polymeric substrates" AIP Publishing 80 (80): 1088-1090, 2002

26 Yongqiang Ma, "Organic thin film transistors based on stable amorphous ladder tetraazapentacenes semiconductors" Royal Society of Chemistry (RSC) 15 (15): 4894-, 2005

27 Yoshiro Yamashita, "Organic semiconductors for organic field-effect transistors" Informa UK Limited 10 (10): 024313-, 2009

28 Kazuo Takimiya, "Organic Semiconductors Based on [1]Benzothieno[3,2-b][1]benzothiophene Substructure" American Chemical Society (ACS) 47 (47): 1493-1502, 2014

29 Bedrˇich Kosˇata, "Novel liquid crystals based on [1]benzothieno[3,2- b][1]benzothiophene" Informa UK Limited 30 (30): 603-610, 2003

30 David Bilger, "Multi-Scale Assembly of Polythiophene-Surfactant Supramolecular Complexes for Charge Transport Anisotropy" American Chemical Society (ACS) 50 (50): 1047-1055, 2017

31 Yaowu He, "Molecular phase engineering of organic semiconductors based on a [1]benzothieno[3,2-b][1]benzothiophene core" Royal Society of Chemistry (RSC) 6 (6): 95149-95155, 2016

32 Atefeh Y. Amin, "Low-Voltage Organic Field Effect Transistors with a 2-Tridecyl[1]benzothieno[3,2-b][1]benzothiophene Semiconductor Layer" American Chemical Society (ACS) 134 (134): 16548-16550, 2012

33 Alessandra Operamolla, "Low band gap poly(1,4-arylene-2,5-thienylene)s with benzothiadiazole units: Synthesis, characterization and application in polymer solar cells" Elsevier BV 95 (95): 3490-3503, 2011

34 Hiroaki Iino, "Liquid crystals for organic thin-film transistors" Springer Science and Business Media LLC 6 (6): 6828-, 2015

35 Hiroaki Iino, "Liquid crystalline organic semiconductors for organic transistor applications" Springer Science and Business Media LLC 49 (49): 23-30, 2016

36 Q. Ye, "Liquid Crystalline Polymers" Springer International Publishing 417-436, 2015

37 Jianguo Mei, "Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors" American Chemical Society (ACS) 135 (135): 6724-6746, 2013

38 Adam Welford, "Influence of alkyl side-chain type and length on the thin film microstructure and OFET performance of naphthalene diimide-based organic semiconductors" Elsevier BV 75 : 105378-, 2019

39 Zhiying Ma, "Influence of alkyl side-chain length on the carrier mobility in organic semiconductors: herringbone vs. pi–pi stacking" Royal Society of Chemistry (RSC) 4 (4): 4546-4555, 2016

40 Hiroaki Iino, "Improved thermal stability in organic FET fabricated with a soluble BTBT derivative" Elsevier BV 358 (358): 2516-2519, 2012

41 Moon Jong Han, "Highly Oriented Liquid Crystal Semiconductor for Organic Field-Effect Transistors" American Chemical Society (ACS) 4 (4): 1495-1502, 2018

42 Hiroaki Iino, "High Uniformity and High Thermal Stability of Solution-Processed Polycrystalline Thin Films by Utilizing Highly Ordered Smectic Liquid Crystals" IOP Publishing 51 : 11PD02-, 2012

43 Yaowu He, "High Performance OTFTs Fabricated Using a Calamitic Liquid Crystalline Material of 2-(4-Dodecyl phenyl)[1]benzothieno[3,2-b][1]benzothiophene" Wiley 2 (2): 1600179-, 2016

44 Yaowu He, "High Performance OTFTs Fabricated Using a Calamitic Liquid Crystalline Material of 2-(4-Dodecyl phenyl)[1]benzothieno[3,2-b][1]benzothiophene" Wiley 2 (2): 1600179-, 2016

45 Hakan Usta, "High Electron Mobility in [1]Benzothieno[3,2-b][1]benzothiophene-Based Field-Effect Transistors: Toward n-Type BTBTs" American Chemical Society (ACS) 31 (31): 5254-5263, 2019

46 Seul-ong Kim, "H-Aggregation Strategy in the Design of Molecular Semiconductors for Highly Reliable Organic Thin Film Transistors" Wiley 21 (21): 1616-1623, 2011

47 C.D. Sheraw, "Functionalized Pentacene Active Layer Organic Thin-Film Transistors" Wiley 15 (15): 2009-2011, 2003

48 Tatsuya Yamamoto, "Facile Synthesis of Highly π-Extended Heteroarenes, Dinaphtho[2,3-b:2‘,3‘-f]chalcogenopheno[3,2-b]chalcogenophenes, and Their Application to Field-Effect Transistors" American Chemical Society (ACS) 129 (129): 2224-2225, 2007

49 Satoru Inoue, "Extended and Modulated Thienothiophenes for Thermally Durable and Solution-Processable Organic Semiconductors" American Chemical Society (ACS) 30 (30): 5050-5060, 2018

50 Satoru Inoue, "Emerging Disordered Layered-Herringbone Phase in Organic Semiconductors Unveiled by Electron Crystallography" American Chemical Society (ACS) 34 (34): 72-83, 2021

51 Satoru Inoue, "Effects of Substituted Alkyl Chain Length on Solution-Processable Layered Organic Semiconductor Crystals" American Chemical Society (ACS) 27 (27): 3809-3812, 2015

52 Chong-Kyu Shin, "Effect of alkyl side-chain length and solvent on the luminescent characteristics of poly(3-n-alkylthiophene)" Elsevier BV 140 (140): 177-181, 2004

53 Jangdae Youn, "Diperfluorophenyl Fused Thiophene Semiconductors for n-Type Organic Thin Film Transistors (OTFTs)" Wiley 1 (1): 1500098-, 2015

54 Christian Ruzié, "Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives" Royal Society of Chemistry (RSC) 4 (4): 4863-4879, 2016

55 Kazuo Takimiya, "Design strategy for air-stable organic semiconductors applicable to high-performance field-effect transistors" Informa UK Limited 8 (8): 273-276, 2007

56 Xiaojun Guo, "Current Status and Opportunities of Organic Thin-Film Transistor Technologies" Institute of Electrical and Electronics Engineers (IEEE) 64 (64): 1906-1921, 2017

57 Yiliang Wu, "Controlled orientation of liquid-crystalline polythiophene semiconductors for high-performance organic thin-film transistors" AIP Publishing 86 (86): 142102-, 2005

58 Yulan Huang, "Controllable thin-film morphology and structure for 2,7-dioctyl[1]benzothieno[3,2- b ][1]benzothiophene (C8BTBT) based organic field-effect transistors" Elsevier BV 36 : 73-81, 2016

59 Takamichi Mori, "Consecutive Thiophene-Annulation Approach to π-Extended Thienoacene-Based Organic Semiconductors with [1]Benzothieno[3,2-b][1]benzothiophene (BTBT) Substructure" American Chemical Society (ACS) 135 (135): 13900-13913, 2013

60 Wolfgang Rao Bodlos, "Cold Crystallization of the Organic n-Type Small Molecule Semiconductor 2-Decyl-7-phenyl-[1]benzothieno[3,2-b][1]benzothiophene S,S,S′,S′-Tetraoxide" American Chemical Society (ACS) 21 (21): 325-332, 2020

61 J. W. Goodby, "Characterization of a new helical smectic liquid crystal" Springer Science and Business Media LLC 337 (337): 449-452, 1989

62 Hiroaki Iino, "Availability of Liquid Crystallinity in Solution Processing for Polycrystalline Thin Films" Wiley 23 (23): 1748-1751, 2011

63 Keqiang He, "Asymmetric Conjugated Molecules Based on [1]Benzothieno[3,2-b][1]benzothiophene for High-Mobility Organic Thin-Film Transistors: Influence of Alkyl Chain Length" American Chemical Society (ACS) 9 (9): 35427-35436, 2017

64 Shenghui Guo, "Alkoxy substituted [1]benzothieno[3,2-b][1]benzothiophene derivative with improved performance in organic thin film transistors" Elsevier BV 56 : 68-75, 2018

65 Luisa Torsi, "A sensitivity-enhanced field-effect chiral sensor" Springer Science and Business Media LLC 7 (7): 412-417, 2008

66 Song Hee Park, "A polymer brush organic interlayer improves the overlying pentacene nanostructure and organic field-effect transistor performance" Royal Society of Chemistry (RSC) 21 (21): 15580-, 2011

67 M. Rajeshkumar Reddy, "2-Thiopene[1]benzothieno[3,2-b]benzothiophene derivatives as solution-processable organic semiconductors for organic thin-film transistors" Elsevier BV 235 : 153-159, 2018

68 Kazuo Takimiya, "2,7-Diphenyl[1]benzothieno[3,2-b]benzothiophene, A New Organic Semiconductor for Air-Stable Organic Field-Effect Transistors with Mobilities up to 2.0 cm² V^-1 s^-1" American Chemical Society (ACS) 128 (128): 12604-12605, 2006