ChemInform Abstract: General Synthesis of Dinaphtho[2,3‐b:2′,3′‐f]thieno[3,2‐b]thiophene (DNTT) Derivatives.

Niimi, Kazuki; Kang, Myeong Jin; Miyazaki, Eigo; Osaka, Itaru; Takimiya, Kazuo

doi:10.1002/chin.201145094

Cited by 3 publications

(7 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Some examples are single-crystal transistors, OFETs with a vertical three-dimensional (3D) channel structure, carbon nanotube enabled vertical OFETs, and devices and circuits fabricated on alkylphosphate-SAM on flexible plastic substrates . Slightly higher mobilities (∼3.5 cm 2 V –1 s –1 ) than those of the parent-DNTT-based devices were recorded by DPh-DNTT-based OFETs . On the other hand, field-effect mobility was further enhanced by the alkylation of DNTT; 2,9-C 10 -DNTT-based OFETs fabricated by vapor deposition showed impressively high mobilities of up to 8 cm 2 V –1 s –1 , which are among the highest for OFETs that are based on a polycrystalline thin film.…”

Section: Molecular Properties and Fet Performancesmentioning

confidence: 90%

“…Although the introduction of the 3-methylthio substituent on 2-naphthaldehyde can be easily done, a concomitant 1-methylthiolated isomer should be removed from the reaction mixture by column chromatography, which hinders its application to scalable synthesis. Alternatively, 2-methoxynaphthalenes are versatile starting materials in the synthesis of DNTT derivatives . After selective introduction of the methylthio moiety at the 3-position of 2-methoxynaphthalenes, conversion of the 2-methoxy into the trifluoromethanesulfonate functionality followed by the Stille-cross coupling reaction with trans -1,2-bis(tributylstannyl)ethene gives the corresponding bis(3-methylthionaphthalen-2-yl)ethenes.…”

Section: Synthesis and Materials Variationmentioning

confidence: 99%

“…The latter synthetic route to the precursors of DNTTs is superior to the former one in terms of easy experimental operation (no chromatographic separation of the isomer is necessary), cost of starting materials, scalability, and total yield (79% for the latter vs 39% total yield for the former in the synthesis of parent DNTT). Taking advantage of those merits, the use of various 2-methoxynaphthalenes with a substituent at the 6- and/or 7-postion has allowed us to synthesize new DNTT derivatives, including 2,9- and 3,10-diphenyl- and 3,10-didecyl-DNTT, and π-extended dianthra[2,3- b :2′,3′- f ]thieno[3,2- b ]thiophene (DATT) …”

Section: Synthesis and Materials Variationmentioning

confidence: 99%

See 2 more Smart Citations

Organic Semiconductors Based on [1]Benzothieno[3,2-b][1]benzothiophene Substructure

et al. 2014

Self Cite

View full text Add to dashboard Cite

The design, synthesis, and characterization of organic semiconductors applicable to organic electronic devices, such as organic field-effect transistors (OFETs) and organic photovoltaics (OPVs), had been one of the most important topics in materials chemistry in the past decade. Among the vast number of materials developed, much expectation had been placed on thienoacenes, which are rigid and planar structures formed by fusing thiophenes and other aromatic rings, as a promising candidate for organic semiconductors for high-performance OFETs. However, the thienoacenes examined as an active material in OFETs in the 1990s afforded OFETs with only moderate hole mobilities (approximately 0.1 cm(2) V(-1) s(-1)). We speculated that this was due to the sulfur atoms in the thienoacenes, which hardly contributed to the intermolecular orbital overlap in the solid state. On the other hand, we have focused on other types of thienoacenes, such as [1]benzothieno[3,2-b][1]benzothiophene (BTBT), which seem to have appropriate HOMO spatial distribution for effective intermolecular orbital overlap. In fact, BTBT derivatives and their related materials, including dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DNTT), have turned out to be superior organic semiconductors, affording OFETs with very high mobilities. To illustrate some examples, we have developed 2,7-diphenyl BTBT (DPh-BTBT) that yields vapor-deposited OFETs having mobilities of up to 2.0 cm(2) V(-1) s(-1) under ambient conditions, highly soluble dialkyl-BTBTs (Cn-BTBTs) that afford solution-processed OFETs with mobilities higher than 1.0 cm(2) V(-1) s(-1), and DNTT and its derivatives that yield OFETs with even higher mobilities (>3.0 cm(2) V(-1) s(-1)) and stability under ambient conditions. Such high performances are rationalized by their solid-state electronic structures that are calculated based on their packing structures: the large intermolecular orbital overlap and the isotropic two-dimensional electronic structure are the key regardless of the molecular size and substituents on the BTBT and its related thienoacene cores. Along with the discovery of such attracting performances, versatile and practical methods for the synthesis of BTBT and its derivatives, and the π-extended derivatives including DNTT, dianthra[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DATT), and the thienoacenes with two thieno[3,2-b]thiophene moieties, have been developed. In addition, the materials have been recently utilized in sophisticated devices and circuits, including all-printed transistor arrays, flexible circuits on ultrathin plastic substrates, and biomedical applications, underscoring their promise as practical semiconductors for electronic device applications. These exciting results of the present BTBT-based materials are expected to open doors to new horizons of organic semiconductors in terms of practical application and the design and synthesis of far more superior materials.

show abstract

Section: Molecular Properties and Fet Performancesmentioning

confidence: 90%

Section: Synthesis and Materials Variationmentioning

confidence: 99%

Section: Synthesis and Materials Variationmentioning

confidence: 99%

See 1 more Smart Citation

Organic Semiconductors Based on [1]Benzothieno[3,2-b][1]benzothiophene Substructure

et al. 2014

Self Cite

View full text Add to dashboard Cite

show abstract

“…The gate dielectric is a stack of plasma-grown aluminum oxide (AlO x ) and a phosphonic acid self-assembled monolayer (SAM) with a thickness of 8 nm and a unit-area capacitance of 0.7 μF/cm 2 ( 36 ). Two different vacuum-deposited small-molecule organic semiconductors, namely, 2,9-diphenyl-dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (DPh-DNTT) ( 37 ) and ActivInk N1100 ( 38 ), were used for the p-channel and n-channel TFTs, respectively. Before the deposition of the organic semiconductors, the surface of the source and drain contacts was functionalized with a chemisorbed monolayer of either pentafluorobenzenethiol (PFBT) or benzyl mercaptan (BM) to minimize the contact resistance in the p-channel and n-channel TFTs, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…In the last process step, the organic semiconductor was deposited by thermal sublimation in vacuum (background pressure, 10 −7 mbar; deposition rate, 0.03 nm/s) through a manually aligned stencil mask ( 24 ). The small-molecule semiconductors DPh-DNTT (Nippon Kayaku; provided by K. Ikeda, Y. Sadamitsu, and S. Inoue) and N , N ′-bis(2,2,3,3,4,4,4-heptafluorobutyl)-1,7-dicyano-perylene-(3,4:9,10)-tetracarboxylic diimide [PTCDI-(CN) 2 -(CH 2 C 3 F 7 ) 2 ; ActivInk N1100; Polyera Corp., Skokie, IL, USA] were used for the p-channel and n-channel TFTs, respectively ( 37 , 38 ). During the organic-semiconductor deposition, the substrate holder was heated to a temperature of 90°C (DPh-DNTT) or 140°C (N1100).…”

Section: Methodsmentioning

confidence: 99%

Nanoscale flexible organic thin-film transistors

et al. 2022

View full text Add to dashboard Cite

Direct-write electron-beam lithography has been used to fabricate low-voltage p-channel and n-channel organic thin-film transistors with channel lengths as small as 200 nm and gate-to-contact overlaps as small as 100 nm on glass and on flexible transparent polymeric substrates. The p-channel transistors have on/off current ratios as large as 4 × 10 9 and subthreshold swings as small as 70 mV/decade, and the n-channel transistors have on/off ratios up to 10 8 and subthreshold swings as low as 80 mV/decade. These are the largest on/off current ratios reported to date for nanoscale organic transistors. Inverters based on two p-channel transistors with a channel length of 200 nm and gate-to-contact overlaps of 100 nm display characteristic switching-delay time constants between 80 and 40 ns at supply voltages between 1 and 2 V, corresponding to a supply voltage–normalized frequency of about 6 MHz/V. This is the highest voltage-normalized dynamic performance reported to date for organic transistors fabricated by maskless lithography.

show abstract

High-gain, low-voltage unipolar logic circuits based on nanoscale flexible organic thin-film transistors with small signal delays

et al. 2023

View full text Add to dashboard Cite

One of the circuit topologies for the implementation of unipolar integrated circuits (circuits that use either p-channel or n-channel transistors, but not both) is the zero- V GS architecture. Zero- V GS circuits often provide excellent static performance (large small-signal gain and large noise margins), but they suffer from the large signal delay imposed by the load transistor. To address this limitation, we have used electron-beam lithography to fabricate zero- V GS circuits based on organic transistors with channel lengths as small as 120 nm on flexible polymeric substrates. For a supply voltage of 3 V, these circuits have characteristic signal-delay time constants of 14 ns for the low-to-high transition and 560 ns for the high-to-low transition of the circuit’s output voltage. These signal delays represent the best dynamic performance reported to date for organic transistor–based zero- V GS circuits. The signal-delay time constant of 14 ns is also the smallest signal delay reported to date for flexible organic transistors.

show abstract

ChemInform Abstract: General Synthesis of Dinaphtho[2,3‐b:2′,3′‐f]thieno[3,2‐b]thiophene (DNTT) Derivatives.

Cited by 3 publications

References 1 publication

Organic Semiconductors Based on [1]Benzothieno[3,2-b][1]benzothiophene Substructure

Organic Semiconductors Based on [1]Benzothieno[3,2-b][1]benzothiophene Substructure

Nanoscale flexible organic thin-film transistors

High-gain, low-voltage unipolar logic circuits based on nanoscale flexible organic thin-film transistors with small signal delays

Contact Info

Product

Resources

About