+

WO2018226865A1 - Modificateurs d'électrode polymères - Google Patents

Modificateurs d'électrode polymères Download PDF

Info

Publication number
WO2018226865A1
WO2018226865A1 PCT/US2018/036311 US2018036311W WO2018226865A1 WO 2018226865 A1 WO2018226865 A1 WO 2018226865A1 US 2018036311 W US2018036311 W US 2018036311W WO 2018226865 A1 WO2018226865 A1 WO 2018226865A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
electrodes
layer
contact
organic semiconductor
Prior art date
Application number
PCT/US2018/036311
Other languages
English (en)
Inventor
Zhihua Chen
Darwin Scott Bull
Mark Seger
Timothy Chiu
Yu Xia
Antonio Facchetti
Original Assignee
Flexterra, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Flexterra, Inc. filed Critical Flexterra, Inc.
Priority to US16/620,094 priority Critical patent/US10886471B2/en
Publication of WO2018226865A1 publication Critical patent/WO2018226865A1/fr

Links

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/80—Constructional details
    • H10K10/82—Electrodes
    • H10K10/84—Ohmic electrodes, e.g. source or drain electrodes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/464—Lateral top-gate IGFETs comprising only a single gate

Definitions

  • This application relates to optical, electronic, and optoelectronic device having surface-modified electrodes.
  • SAM Self-assembled monolayers
  • a typical example of a SAM is the adsorption of alkylthiols onto a gold surface.
  • the thiol "head group” initially physisorbs to the gold surface and is eventually converted to a chemisorbed Au-thiolate.
  • the alkyl "tails” also interact with each other via van der Waals interactions to form ordered structures.
  • SAMs have been extensively studied from a theoretical and practical perspective and have found utility in the fields of corrosion prevention, adhesives, and lubrication.
  • Thiolate-based SAMs also have found use in organic electronic devices to achieve higher charge carrier mobility and increased on-current. The actual mechanism is thought to be related to either the reduction of the Schottky energy barrier between metal electrodes and organic semiconductors, and/or the modification of the crystal morphology of the organic semiconductor.
  • OOTFT organic thin film transistor
  • different thiols have been shown to either increase the work function of metal electrodes to match the highest occupied molecular orbital (HOMO) energy of p-type semiconductors, or to lower the work function of metal electrodes to match the lowest unoccupied molecular orbital (LUMO) energy of n-type semiconductors.
  • the present teachings relate to polymeric electrode modifiers that can be used to improve the performance of organic electronic devices. Unlike current thiolate-based SAM treatment, the present polymeric electrode modifiers can provide more stabilized surfaces, which in turn leads to more stable device performance.
  • the present polymeric electrode modifiers are derived from an episulfide monomer (also known as a thiirane) of the formula:
  • the episulfide monomer polymerizes into a polymer having a repeating unit of the formula:
  • n can be an integer ranging from 3 to 1,000 (inclusive).
  • the present teachings provide a method for modifying one or more metal or metal alloy electrodes in an optical, electronic, or optoelectronic device.
  • the method includes contacting the one or more electrodes with a composition including a polymeric electrode modifier according to the present teachings, forming a surface-modifying layer in contact with the surfaces of the one or more electrodes.
  • a composition including a polymeric electrode modifier according to the present teachings forming a surface-modifying layer in contact with the surfaces of the one or more electrodes.
  • the present teachings relate to optical, electronic, or optoelectronic device that include one or more electrodes composed of a metal or metal alloy, wherein the surface of at least one of the one or more electrodes is in contact with a surface- modifying layer that includes the present polymer.
  • the device for example, can be an organic thin film transistor that includes a substrate, an organic semiconductor layer, source and drain electrodes in contact with the organic semiconductor layer, a gate dielectric layer, and a gate electrode in contact with the gate dielectric layer, where the surfaces of the source and drain electrodes are in contact with the surface-modifying layer.
  • Fig. 1 illustrates a thin film transistor structure incorporating source and drain electrodes treated with a polymeric surface-modifying layer according to the present teachings.
  • the thin film transistor as shown has a top-gate bottom-contact configuration, which includes a substrate 1, a buffer/planarization layer 2, source and drain electrodes 3, a polymeric surface-modifying layer 4, an organic semiconductor layer 5, a gate dielectric 6, and a gate electrode 7.
  • Fig. 2 is a schematic diagram illustrating how PCHES may arrange itself on the surface of a silver (Ag) electrode.
  • Fig. 3 shows the 1H NMR spectrum of PCHES.
  • Fig. 4 illustrates the transfer characteristics and mobility evolution (inset) of thin- film transistors including source and drain electrodes treated according to the present teachings (specifically, with PCHES).
  • Fig. 5 illustrates the transfer characteristics of TFTs employing different contact treatments. Specifically, the transfer plots of two different thin film transistors including source and drain electrodes treated according to the present teachings (respectively, with PCHES, and a 1 : 1 CHES: PCHES mixture formulation) are compared against those of two comparative thin film transistors including source and drain electrodes either with no treatment or treated with the monomer CHES only.
  • Fig. 6 compares the mobility evolution of TFTs employing different
  • Fig. 7 shows the effect of annealing (before and after annealing at 130°C for 5 minutes, 15 minutes, and 45 minutes) on the saturation mobility of thin film transistors.
  • Thin film transistors including source and drain electrodes treated according to the present teachings specifically, with PCHES
  • PCHES PCHES
  • MOTP a standard thiol work-function modifier
  • Fig. 8 shows the long term stability of thin film transistors including source and drain electrodes treated according to the present teachings (specifically, with PCHES) compared to thin film transistors including source and drain electrodes treated with a standard thiol (specifically, MoTP), where long term stability was demonstrated via the lack of on- current degradation.
  • Fig. 9 compares the transfer characteristics of TFTs having contacts treated with PCHES (as a separate step from the deposition of the organic semiconductor layer) versus TFTs having contacts treated via a one-step process using a formulation including both PCHES and the organic semiconductor.
  • compositions are described as having, including, or comprising specific components, or where processes are described as having, including, or comprising specific process steps, it is contemplated that compositions of the present teachings also consist essentially of, or consist of, the recited components, and that the processes of the present teachings also consist essentially of, or consist of, the recited process steps.
  • a ' ⁇ polymeric compound refers to a molecule including a plurality of one or more repeating units connected by covalent chemical bonds.
  • a polymeric compound can be represented by the general formula: wherein M is the repeating unit or monomer.
  • the polymeric compound can have only one type of repeating unit as well as two or more types of different repeating units. When a polymeric compound has only one type of repeating unit, it can be referred to as a homopolymer. When a polymeric compound has two or more types of different repeating units, the term "copolymer” or “copolymeric compound” can be used instead.
  • a copolymeric compound can include repeating units
  • the assembly of the repeating units in the copolymer can be head-to-tail, head-to-head, or tail-to- tail.
  • the copolymer can be a random copolymer, an alternating copolymer, or a block copolymer. For example, the general formula:
  • a polymeric compound can be further characterized by its degree of polymerization (n) and molar mass (e.g., number average molecular weight (Mn) and/or weight average molecular weight (M w ) depending on the measuring technique(s)).
  • solution-processable refers to compounds (e.g., polymers), materials, or compositions that can be used in various solution-phase processes including spin-coating, printing (e.g., inkjet printing, gravure printing, offset printing and the like), spray coating, electrospray coating, drop casting, dip coating, and blade coating.
  • a "p-type semiconductor material” or a “donor” material refers to a semiconductor material, for example, an organic semiconductor material, having holes as the majority current or charge carriers.
  • a p-type semiconductor material when deposited on a substrate, it can provide a hole mobility in excess of about 10" 5 cm 2 /Vs.
  • a p-type semiconductor In the case of field-effect devices, a p-type semiconductor also can exhibit a current on/off ratio of greater than about 10.
  • an "n-type semiconductor material” or an “acceptor” material refers to a semiconductor material, for example, an organic semiconductor material, having electrons as the majority current or charge carriers.
  • an n-type semiconductor material when deposited on a substrate, it can provide an electron mobility in excess of about 10 "3 cm 2 /Vs. In the case of field-effect devices, an n-type semiconductor also can exhibit a current on/off ratio of greater than about 10.
  • mobility refers to a measure of the velocity with which charge carriers, for example, holes (or units of positive charge) in the case of a p-type semiconductor material and electrons (or units of negative charge) in the case of an n-type semiconductor material, move through the material under the influence of an electric field.
  • charge carriers for example, holes (or units of positive charge) in the case of a p-type semiconductor material and electrons (or units of negative charge) in the case of an n-type semiconductor material
  • the present teachings relate to novel polymeric materials for electrode treatment that can yield the performance benefits offered by current self-assembled monolayer technology (typically, via small-molecule thiols) without the drawback of unstable device performance.
  • the present polymeric electrode modifiers can be used to achieve high charge carrier mobility and increased on-current in organic electronic devices, while conferring advantages such as improved thermal stability and long-term environmental stability over small-molecule thiol treatment.
  • the present polymeric electrode modifiers can be derived from an episulfide monomer of the formula:
  • the episulfide monomer can be selected from the group consisting of cyclohexene episulfide (C6), cyclopentene episulfide (C5), cycloheptene episulfide (C7), and cyclooctene episulfide (C8):
  • the episulfide monomer can include larger (e.g., having 10-20 carbon atoms) polycyclic (e.g., bicyclic or tricyclic) group, an example of which is dicyclopentene episulfide.
  • the episulfide monomer can be cyclohexene sulfide
  • the episulfide monomer can polymerize into a polymer having a repeating unit of the formula:
  • n which defines the degree of polymerization of the polymer
  • n can be an integer ranging from 3 to 1,000 (inclusive).
  • the present polymer can have a degree of polymerization (n) ranging from 10 to 50 (inclusive).
  • the polymer can have a repeating unit selected from the group consisting of:
  • the polymerization reaction can be self-limiting, and the end groups of the present polymer can be a thiol group. In other embodiments, the polymerization reaction can be terminated by adding a quencher or an inhibitor.
  • a specific embodiment of the present polymer can be poly-CHES (PCHES): where Ei and E2 are identical or different end groups selected from the group consisting of H, R 1 , NH2, NHR 1 , N(R 1 ) 2 , SH, SR 1 , and OR 1 , where R 1 , at each occurrence, independently can be selected from the group consisting of a Ci-10 alkyl group, a Ci-10 alkenyl group, and a phenyl group. More generally, the present polymer can be of the formula:
  • the present polymeric electrode modifier can be soluble in various common organic solvents.
  • a compound can be considered soluble in a solvent when at least 0.1 mg of the compound can be dissolved in 1 mL of the solvent.
  • common organic solvents include petroleum ethers; acetonitrile; aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; ketones such as acetone, and methyl ethyl ketone; ethers such as tetrahydrofuran, dioxane, bis(2-methoxyethyl) ether, diethyl ether, di-isopropyl ether, and t-butyl methyl ether; alcohols such as methanol, ethanol, butanol, and isopropyl alcohol; aliphatic hydrocarbons such as hexanes; esters such as methyl acetate, ethyl acetate, methyl formate, e
  • halogenated aliphatic and aromatic hydrocarbons such as dichloromethane, chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, and trichlorobenzene; and cyclic solvents such as cyclopentanone, cyclohexanone, and 2-methypyrrolidone.
  • the present polymers can have room temperature solubilities in aromatic solvents such as anisole as high as 10 g/L.
  • the polymeric electrode modifiers described herein can be dissolved, dispersed or suspended in a single solvent or mixture of solvents to provide a composition suitable for solution processing techniques.
  • the composition can include the polymeric electrode modifiers as the only active component.
  • the composition also can include an episulfide compound such as any of the episulfide monomers described hereinabove.
  • Common solution-phase processing techniques include, for example, spin coating, slot coating, doctor blading, drop-casting, zone casting, dip coating, blade coating, or spraying.
  • Another example of solution-phase processing technique is printing. As used herein, "printing" includes a noncontact process such as inkjet printing,
  • microdispensing and the like and a contact process such as screen-printing, gravure printing, offset printing, flexographic printing, lithographic printing, pad printing, microcontact printing and the like.
  • the present polymeric electrode modifiers can be dissolved in an organic solvent or solvent mixture to provide a composition which is used to contact one or more electrodes in an optical, electronic, or optoelectronic device, where the one or more electrodes are composed of a metal or metal alloy.
  • the one or more electrodes can be composed of silver, gold, platinum, copper, aluminum, molybdenum, palladium, nickel, or combinations thereof.
  • the electrode can be made of silver.
  • the electrode can be made of gold.
  • the electrodes can be made of molybdenum.
  • the composition including the present polymeric electrode modifier can be contacted with the electrodes by immersing the electrodes into the composition.
  • the composition can be deposited on the electrodes by other solution-phase processing techniques such as spin-coating and blade-coating. Subsequently, any excess amount of the composition can be removed by spin-drying and any unbound polymeric electrode modifiers can be rinsed off. The resulting suiface-modifying layer can form conformally on the surfaces of the electrodes.
  • the sulfur atoms of the present polymeric electrode modifiers can adsorb to metal surfaces in a self-assembled manner similar to standard thiols and sulfides, which helps limit the thickness of the polymeric surface-modifying layer, thereby preventing the polymer film from becoming an electrically insulating layer.
  • a surface-modifying layer composed of the present polymeric electrode modifiers can confer advantages such as thermal stability and long-term environmental stability.
  • treating the electrodes with the present polymeric electrode modifiers can improve charge injection (e.g., by modifying the work function of the metal electrodes to match the orbital energy of the channel layer material), increase the device charge carrier mobility and/or increase the on-current.
  • Fig. 1 illustrates an organic thin film transistor incorporating a surface-modifying layer according to the present teachings. While the top gate-bottom contact architecture is illustrated, other configurations (e.g., bottom gate-bottom contact) also can be used.
  • the thin film transistor generally includes a substrate 1 (usually glass or plastic).
  • An optional planarization layer 2 can be present on the substrate.
  • the source and drain electrodes 3 are formed either directly on the substrate or on the planarization layer (if present).
  • the source/drain electrodes can be formed using various deposition techniques. For example, the electrodes can be deposited through a mask, or can be deposited then etched or lifted off (photolithography). Suitable deposition techniques include electrodeposition, vaporization, sputtering, electroplating, coating, laser ablation and offset printing, from metal or metal alloy including copper, aluminum, gold, silver, molybdenum, platinum, palladium, and/or nickel.
  • the source and drain electrodes can be treated with the present polymeric electrode modifiers as described above to provide a surface-modifying layer 4.
  • the organic semiconductor layer (i.e., the channel layer) 5 can be deposited via various solution-phase processing techniques. With respect to the composition of the channel layer, various p-type
  • n-type semiconductors can be used.
  • Examples of p-type semiconductors include to oligothiophenes, polythiophenes, and various pentacene compounds known in the art.
  • Examples of n-type semiconductors include fluorocarbon-substituted thiophene oligomers and polymers, cyanated perylene diimides and cyanated naphthalene diimides, to name a few.
  • a gate dielectric layer 6 is deposited on top of the organic semiconductor layer, and the gate electrode 7 can be formed on top of the gate dielectric layer using the same deposition techniques as the source and drain electrodes.
  • a composition including both the present polymeric electrode modifier and a suitable organic semiconducting compound can be used instead of carrying two separate steps to form the surface-modifying layer and the channel layer.
  • a composition including both the present polymeric electrode modifier and a suitable organic semiconducting compound can be used instead.
  • the composition including both the present polymeric electrode modifier and a suitable organic semiconducting compound can be contacted with the source and drain electrodes.
  • the sulfur atoms of the present polymeric electrode modifiers can adsorb to the surfaces of the metal (e.g., Ag) source and drain electrodes in a self-assembled manner as illustrated in Fig. 2.
  • the organic semiconducting compound in the composition can provide the channel layer adjacent to the surface-modifying layer.
  • devices prepared by this one-step process manifested similar electrical characteristics as conventional devices where the surface-modifying layer and the organic semiconductor layer were formed in two separate steps.
  • the present surface modifiers also provide the advantage of simplifying the device fabrication process.
  • Example la Preparation of PCHES-1: A solution of cyclohexene sulfide (CHES) (0.82 g, 6.92 mmol) in THF (5 mL) was well stirred at room temperature.
  • CHES cyclohexene sulfide
  • Fig. 3 provides the 1H NMR spectrum of PCHES-2.
  • Example 2 Synthesis of Additional Polymeric Electrode Modifiers
  • cyclic thiirane monomers having different ring sizes could be used to synthesize additional polymeric electrode modifiers according to the present teachings.
  • thiirane monomers such as cyclopentene sulfide, cycloheptene sulfide, and cyclooctene sulfide, could be synthesized from their corresponding epoxides by employing potassium thiocyanate or thiourea. See e.g., Chen et al., Tetrahedron Lett..
  • the present polymer also can be achieved from various cyclic thiirane monomers described herein via nucleophilic polymerization. See e.g., Lautenschlaeger et al, J. Polvm. Sci. Part A-1. 8: 2579-2594 (1970), and Culvenor et al, J. Chem. Soc. 282-287 (1949).
  • Scheme 4 illustrates the preparation of PCHES via nucleophilic polymerization from cyclohexene sulfide.
  • Example 3 Thin-Film Transistors with PCHES-Treated Electrodes
  • a photocurable planarization layer 2 was spin-coated, then UV -cured and baked.
  • the source and drain contacts (silver) 3 were then formed via thermal evaporation through a shadow mask.
  • the contacts were treated by immersion in an anisole solution of PCHES (1 mg/ml PCHES- 1 in anisole, see Example la) for 30 seconds, followed by spin-drying and rinsing with fresh anisole to remove unbound PCHES.
  • the resulting layer is illustrated as a work-function modifier layer (or surface-modifying layer) 4 in Fig. 1.
  • the devices were completed by spin- coating the semiconductor layer 5 (in this case, composed of an N-type organic
  • the channel dimensions were 60 um (L) by 1000 um (W).
  • the capacitance of the gate insulator layer was 3.0 nF/cm 2 .
  • L and W are the device channel length and width, respectively
  • G is the capacitance of the oxide insulator (1 x 10-8 F/cm 2 for 300 nm S1O2)
  • Vt is the threshold voltage
  • Fig. 4 shows the device performance of a representative PCHES-treated transistor.
  • the mean charge carrier mobility was around 0.8 cmWs as shown in the inset.
  • FIG. 5 shows the device performance of a representative PCHES:CHES-treated transistor.
  • the mean charge carrier mobility was around 0.6 cm 2 /Vs.
  • Comparative Example 3 Comparative Thin-Film Transistors
  • Comparative transistors were fabricated in a manner similar to Example 3, except that the source and drain electrodes were treated with different conditions: a) no work- function modifier, and b) the monomer cyclohexene sulfide (CHES) was used in lieu of PCHES. Representative electrical performance of the two comparative devices is shown in Fig. 5 (versus the electrical performance of the two devices of Example 3).
  • the mean charge carrier mobilities were 0.04 cmWs for the no-work function modifier devices, and 0.09 cm 2 /Vs for the monomer CHES-treated devices, respectively.
  • Comparative transistors were fabricated with a standard small molecule thiol (2- methoxythiophenol, MOTP) known to be a good work-function modifier for N-type organic TFTs. See Boudinet et al., Organic Electronics, 11: 227-237 (2010).
  • Fig. 6 shows the mobility evolution of TFTs employing different concentrations of a) PCHES and b) MOTP treatment. It can be seen that to achieve a mobility of around 0.8 cm 2 /V s, only a concentration of 1 mg/ml or less is needed when PCHES treatment was employed. By comparison, to achieve a mobility of around 0.8 cmWs, a much higher concentration, i.e., at least 10 mg/ml, of MOTP was needed, which is 10 times higher than the PCHES treatment.
  • PCHES-treated transistors were fabricated according to the procedures described in Example 1, except that they were also annealed at 130°C in air on a hot plate after the device was completed. Electrical characteristics were measured under room temperature before annealing (0 min), after a 5 -minute annealing cycle (5 min), after a second 10-minute annealing cycle (total annealing time: 15 min), and after a third 30-minute annealing cycle (total annealing time: 45 min).
  • Comparative transistors were fabricated with MOTP electrode treatment according to the procedures described in Example 4. The completed devices were annealed at 130°C in air on a hot plate for different durations. Similar to the PCHES-treated devices, electrical characteristics of the comparative devices were measured under room temperature before annealing (0 min), after a 5-minute annealing cycle (5 min), after a second 10-minute annealing cycle (total annealing time: 15 min), and after a third 30-minute annealing cycle (total annealing time: 45 min). [0069] As shown in Fig. 7, the PCHES-treated transistors showed negligible variations in mobility after continuous annealing, suggesting that the source and drain treatment according to the present teachings helps maintain device stability against heat treatment.
  • the thiol-treated transistors experienced a pronounced degradation in mobility upon continuous annealing (from -1.2 cm 2 /Vs before annealing to -0.9 cmWs after 45 minutes of annealing at 130°C).
  • This example illustrates the long-term stability of PCHES-treated transistors.
  • PCHES-treated transistors were fabricated according to the procedures described in Example 1. The completed devices were stored in an environmental chamber under 70°C and 23% relative humidity. Electrical characterization was performed in-situ to investigate the TFT stability over the course of 10 days.
  • Comparative transistors were fabricated with MOTP electrode treatment according to the procedures described in Example 4. Similar to the PCHES-treated devices, the completed devices were stored in an environmental chamber under 70°C and 23% relative humidity, and electrical characterization was performed in-situ to investigate the TFT stability over the course of 10 days.
  • Fig. 8 shows the observed changes in on-current over time. As shown in Fig. 8, the PCHES-treated transistors showed less than 20% degradation in the on-current after being in storage for 10 consecutive days.
  • Example 7 One-Step Process Evaluation
  • Fig. 9 illustrates the electrical characteristics of the one-step TFT vis-a-vis the PCHES-treated TFT fabricated according to the procedures described in Example 1. As shown in Fig. 9, the electrical characteristics of the two types of devices are comparable, demonstrating that the surface treatment according to the present teachings further provides an advantage of simplifying the device fabrication process.
  • sample devices were prepared. First, a photocurable planarization layer 2 was spin-coated onto a suitable substrate 1, then UV-cured and baked. Next, a metal layer composed of either silver or gold 3 was formed via thermal evaporation without a mask. The metal layer was treated by immersion in an anisole solution of PCHES (1 mg/ml PCHES-1 in anisole) for 30 seconds, followed by spin-drying and rinsing with fresh anisole to remove unbound PCHES. The work function of the metal layer surfaces was measured by Ultraviolet Photoelectron Spectroscopy (UPS) and compared with untreated metal surfaces.
  • UPS Ultraviolet Photoelectron Spectroscopy

Landscapes

  • Thin Film Transistor (AREA)

Abstract

La présente invention concerne de nouveaux matériaux polymères pour le traitement d'électrodes. Les présents modificateurs d'électrode polymères peuvent être dérivés d'un monomère épisulfure par l'intermédiaire d'une réaction de polymérisation par ouverture de cycle catalysée par un acide ou d'une réaction de polymérisation nucléophile.
PCT/US2018/036311 2017-06-07 2018-06-06 Modificateurs d'électrode polymères WO2018226865A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US16/620,094 US10886471B2 (en) 2017-06-07 2018-06-06 Polymeric electrode modifiers

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201762516630P 2017-06-07 2017-06-07
US62/516630 2017-06-07
IT201700076313 2017-07-06
IT102017000076313 2017-07-06

Publications (1)

Publication Number Publication Date
WO2018226865A1 true WO2018226865A1 (fr) 2018-12-13

Family

ID=60570017

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2018/036311 WO2018226865A1 (fr) 2017-06-07 2018-06-06 Modificateurs d'électrode polymères

Country Status (1)

Country Link
WO (1) WO2018226865A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040161873A1 (en) * 2002-11-25 2004-08-19 Dimitrakopoulos Christos D. Organic underlayers that improve the performance of organic semiconductors
GB2536426A (en) * 2015-03-13 2016-09-21 Cambridge Display Tech Ltd Polymer blends for a semiconducting layer of an organic electronic device

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040161873A1 (en) * 2002-11-25 2004-08-19 Dimitrakopoulos Christos D. Organic underlayers that improve the performance of organic semiconductors
GB2536426A (en) * 2015-03-13 2016-09-21 Cambridge Display Tech Ltd Polymer blends for a semiconducting layer of an organic electronic device

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
AZIZI ET AL., SYNLETT., vol. 5, 2014, pages 1085 - 1088
BOUDINET D ET AL: "Modification of gold source and drain electrodes by self-assembled monolayer in staggered n- and p-channel organic thin film transistors", ORGANIC ELECTRONICS, ELSEVIER, AMSTERDAM, NL, vol. 11, no. 2, 30 October 2009 (2009-10-30), pages 227 - 237, XP026836245, ISSN: 1566-1199, [retrieved on 20091030] *
BOUDINET ET AL., ORGANIC ELECTRONICS, vol. 11, 2010, pages 227 - 237
CHEN ET AL., TETRAHEDRON LET, vol. 58, 2017, pages 1651 - 1654
CULVENOR ET AL., J. CHEM. SOC., 1949, pages 282 - 287
DARENSBOURG ET AL., MACROMOLECULES, vol. 46, 2013, pages 8102 - 8110
EISAVI ET AL., J. SULFUR CHEM., vol. 37, 2016, pages 537 - 545
EISAVI ET AL., PHOSPHORUS, SULFUR. SILICON RELAT. ELEM., vol. 191, 2016, pages 65 - 69
LAUTENSCHLAEGER ET AL., J. POLVM. SCI. PART A-1, vol. 8, 1970, pages 2579 - 2594
MIRZA-AGHAYAN ET AL., J. SULFUR CHEM., vol. 36, 2015, pages 30 - 35
VERESHCHAGINA ET AL., PETROLEUM CHEM., vol. 54, 2014, pages 207 - 212

Similar Documents

Publication Publication Date Title
US9537102B2 (en) Fused polycyclic heteroaromatic compound, organic thin film including compound and electronic device including organic thin film
JP5745278B2 (ja) 有機半導体配合物
EP3050887B1 (fr) Composé hétéroaromatique polycyclique fusionné, film mince organique comprenant un composé et dispositif électronique comprenant le film mince organique
US8329915B2 (en) Thienothiophene derivatives
US20070275501A1 (en) Fabricating tft having fluorocarbon-containing layer
TW201302744A (zh) 作為有機半導體之萘－二醯亞胺－雜環－萘二醯亞胺低聚物以及自其產生之電晶體
EP2910556A1 (fr) Nouveau composé aromatique polycyclique condensé et son utilisation
EP3275884B1 (fr) Composé organique, matériau organique semi-conducteur, film organique mince et son procédé de production, composition organique semi-conductrice et dispositif organique semi-conducteur
CA2583020C (fr) Polyalkynylthiophenes et composants ainsi crees
EP3656775B1 (fr) Composé, film mince organique, transistor à film mince et dispositif électronique
JP6465799B2 (ja) 有機半導体配合物
WO2009105041A1 (fr) Dérivés de dithiénothiophène
US7468329B2 (en) Dedoping of organic semiconductors
US20100090201A1 (en) Organic thin film transistors
US20200225186A1 (en) Ofet-based ethylene gas sensor
KR101450137B1 (ko) 유기반도체용 공중합체 및 이를 이용한 유기박막트랜지스터 및 유기 전자소자
KR101888617B1 (ko) 유기 반도체 화합물, 이를 포함하는 유기 박막, 상기 유기 박막을 포함하는 전자 소자 및 유기 박막의 제조방법
JP2010138395A (ja) ポリチオフェンおよびポリチオフェンを含む電子デバイス
EP2207218B1 (fr) Transistor a effet de champ
US10886471B2 (en) Polymeric electrode modifiers
KR101455600B1 (ko) 유기 박막 트랜지스터 및 그 제조방법
US20090242878A1 (en) Optimization of new polymer semiconductors for better mobility and processibality
WO2018226865A1 (fr) Modificateurs d'électrode polymères
WO2018029160A1 (fr) Procédé pour obtenir une injection de charge efficace pour le transport d'électrons et/ou de trous dans des couches semiconductrices
Kazarinoff et al. OTFT performance of air-stable ester-functionalized polythiophenes

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18732215

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18732215

Country of ref document: EP

Kind code of ref document: A1

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载