High-mobility bottom-contact n-channel organic transistors and their use in complementary ring oscillators

Yoo, Byung Woo; Jung, Taeho; Basu, Debarshi; Dodabalapur, Ananth; Jones, Brian; Facchetti, Antonio; Wasielewski, Michael R.; Marks, Tobin J.

doi:10.1063/1.2177627

Cited by 134 publications

(99 citation statements)

References 21 publications

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“…For example, the crystal structure of an edible ingredient can influence its taste and texture; in the pharmaceutical industry, different crystal polymorphs of the same drug can have drastically different dissolution rates, bioavailability and chemical stability 2,6 . In the field of organic electronics, small aromatic molecules are widely used as the organic semiconductors (OSCs) for thin-film transistors (TFTs) to fabricate a variety of flexible, transparent and bendable electronics [7][8][9][10][11][12] . The OSC chemical structure, together with p-p stacking and van der Waals intermolecular interactions, collectively determine the molecular packing structure.…”

mentioning

confidence: 99%

One-dimensional self-confinement promotes polymorph selection in large-area organic semiconductor thin films

RuiPeng²,

et al. 2014

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A crystal's structure has significant impact on its resulting biological, physical, optical and electronic properties. In organic electronics, 6,13(bis-triisopropylsilylethynyl)pentacene (TIPS-pentacene), a small-molecule organic semiconductor, adopts metastable polymorphs possessing significantly faster charge transport than the equilibrium crystal when deposited using the solution-shearing method. Here, we use a combination of high-speed polarized optical microscopy, in situ microbeam grazing incidence wide-angle X-ray-scattering and molecular simulations to understand the mechanism behind formation of metastable TIPS-pentacene polymorphs. We observe that thin-film crystallization occurs first at the air-solution interface, and nanoscale vertical spatial confinement of the solution results in formation of metastable polymorphs, a one-dimensional and large-area analogy to crystallization of polymorphs in nanoporous matrices. We demonstrate that metastable polymorphism can be tuned with unprecedented control and produced over large areas by either varying physical confinement conditions or by tuning energetic conditions during crystallization through use of solvent molecules of various sizes.

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confidence: 99%

One-dimensional self-confinement promotes polymorph selection in large-area organic semiconductor thin films

RuiPeng²,

et al. 2014

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“…While operating under vacuum, a saturation regime mobility of 2. [12] because of morphological/microstructural irregularities; however, it is the highest organic n-channel solution-processed OFET mobility obtained to date for channel lengths smaller than 10 lm.…”

Section: Nn′-bis(n-octyl)-(17and16)-dicyanoperylene-34:910-bis(dicar-mentioning

confidence: 94%

“…The enabling advance reported here is the successful development of an air-stable n-type organic semiconductor, PDI-8CN 2 , along with compatible solution-deposition processing techniques. Experimental PDI-8CN 2 was synthesized and purified as reported previously [11,12]. The compound was pure, as confirmed by 1 H NMR and elemental analysis.…”

Section: Nn′-bis(n-octyl)-(17and16)-dicyanoperylene-34:910-bis(dicar-mentioning

confidence: 99%

“…[11,12] Because PDI-8CN 2 is soluble in common solvents such as chloroform, toluene, and dichlorobenzene, an intriguing question of whether it could be used for fabricating complex complementary organic circuits using solution-based processing techniques is raised. We report here the first fabrication of highperformance n-channel organic transistors and their complementary circuits from a PDI-8CN 2 solution with a micro-injector patterning technique.…”

Section: Nn′-bis(n-octyl)-(17and16)-dicyanoperylene-34:910-bis(dicar-mentioning

confidence: 99%

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High‐Performance Solution‐Deposited n‐Channel Organic Transistors and their Complementary Circuits

Jones²,

et al. 2007

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Printed electronic circuits have been explored for low-cost, large-area applications, such as displays and radio frequency identification tags, where the promise of inexpensive solutionbased fabrication techniques is more crucial than the fast circuit speeds associated with conventional inorganic semiconductors. [1][2][3][4][5][6][7][8] In order for such low-cost, portable devices to become a reality, high-mobility, air-stable, n-channel organic field-effect transistors (OFETs) are required to enable the fabrication of organic complementary metal oxide semiconductor (CMOS) circuits that would operate at sufficient speeds and with low power dissipation. Additionally, the semiconductors must be solution processable to be compatible with the inexpensive fabrication techniques envisioned for printed electronics. Whereas most examples of printed organic semiconductors are conjugated p-type polymers, solution-processed OFETs with small molecules are far less common. [9,10] Previously, the small molecule semiconductor N,N′-bis(n-octyl)-(1,7&1,6)-dicyanoperylene-3,4:9,10-bis(dicar-boximide) (PDI-8CN 2 ) was used to fabricate promising vapordeposited n-channel OFETs with excellent electrical performance and remarkable environmental stability. [11,12] Because PDI-8CN 2 is soluble in common solvents such as chloroform, toluene, and dichlorobenzene, an intriguing question of whether it could be used for fabricating complex complementary organic circuits using solution-based processing techniques is raised. We report here the first fabrication of highperformance n-channel organic transistors and their complementary circuits from a PDI-8CN 2 solution with a micro-injector patterning technique. This work advances the pioneering results of Katz et al., [13] who fabricated a simple organic complementary inverter with a shadow-masked top-contact geometry. Unfortunately, such simple fabrication methods are not scalable for shrinking channel lengths to technologically useful sizes or for increasing the circuit complexity beyond inverter structures. These last two points represent the crossing of major technical hurdles in the development of organic complementary circuit technology. For the present OFET device fabrication, the organic semiconductor solutions were patterned in a nitrogen atmosphere using an Intracel Picospritzer, a pneumatically actuated micro-injector where droplet size is controlled by gas pressure and jetting time. The OFET gate dielectric and gold source/ drain electrode surfaces were treated with self-assembled monolayers (SAMs) to improve the surface energy match with the organic semiconductors and to produce approximately hemispherical solution droplets. Solvent selection proved crucial to the formation of uniform semiconductor films-for example, low-boiling solvents, such as chloroform, leave residue on the micropipette tip, adversely affecting the deposition process and the resultant film morphology. However, high-boiling solvents, such as 1,2-dichlorobenzene (bp 174°C) do not adversely affect the solution de...

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“…N , NЈ-dialkyl-3,4,9,10-perylene tetracarboxylic diimide ͑PTCDI-Cn͒, especially, is very promising n-type materials with a high electron mobility, and studied intensively from the first stage of researches on OTFTs. [14][15][16][17][26][27][28][29][30][31][32][33][34][35][36][37][38][39] For example, Horowitz et al have reported the first n-type organic TFT made of N , NЈ-diphenyl PTCDI 14 yr ago. 26 After 6 yr, Malenfant et al have reported a N,NЈ-dioctyl PTCDI TFT with fairly high electron mobility as high as 0.6 cm 2 / V s. 27 Jones et al have synthesized corecyanated PTCDI with fluorinated alkyl chains, and reported an air-stable TFT with electron mobility of 0.64 cm 2 / V s. 28 Chesterfield et al have reported strikingly high electron mobility in N , NЈ-dioctyl PTCDI TFT of up to 1.7 cm 2 / V s through exquisite control of deposition condition, 29 and after that many research groups have poured their efforts to develop high-mobility n-type PTCDI OTFTs by modifying the molecular structure with core-substitution or with changing the substituent on the imide N atoms, by controlling deposition condition, by optimizing device structure such as the surface state of dielectrics and electrode contact, and so on.…”

Section: Introductionmentioning

confidence: 99%

Thermal treatment effects on N-alkyl perylene diimide thin-film transistors with different alkyl chain

Jeon¹,

Hattori²,

Kato³

et al. 2010

Journal of Applied Physics

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The authors report that thermal treatment effect on various N , NЈ-dialkyl-3,4,9,10-perylene tetracarbxylic diimides ͓PTCDI-Cn, alkyl-dodecyl ͑n=12͒, butadecyl ͑n=14͒, octadecyl ͑n=18͔͒ thin-film transistors ͑TFTs͒ depends on the substituted alkyl chain length. It is clearly demonstrated that there are two kinds of molecular movements during the thermal treatment on PTCDI films; molecular rearrangement in the same layer and molecular migration from the lower layer to the upper layer. The former is directly related to the grain growth and can be controllable by applying an external electric field. The latter is also related not only to the grain growth but also to the formation of cracks between grains. These two movements show opposite dependence on the alkyl chain length during the thermal treatment; the former is more active in longer alkyl chain, but the latter in shorter one. However, they also have opposite effect to TFT performance, and PTCDI films with longer alkyl chains have great advantage on TFT performance for the thermal treatment. Consequently, PTCDI-C18 TFTs show the highest electron mobility as large as 1.2 cm 2 / V s after the thermal treatment at 140°C.

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High-mobility bottom-contact n-channel organic transistors and their use in complementary ring oscillators

Cited by 134 publications

References 21 publications

One-dimensional self-confinement promotes polymorph selection in large-area organic semiconductor thin films

One-dimensional self-confinement promotes polymorph selection in large-area organic semiconductor thin films

High‐Performance Solution‐Deposited n‐Channel Organic Transistors and their Complementary Circuits

Thermal treatment effects on N-alkyl perylene diimide thin-film transistors with different alkyl chain

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