WO2017194917A1 - Séparation de phase pour une mobilité de porteuse améliorée dans des dispositifs de transistor à couches minces organique - Google Patents

Séparation de phase pour une mobilité de porteuse améliorée dans des dispositifs de transistor à couches minces organique Download PDF

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WO2017194917A1
WO2017194917A1 PCT/GB2017/051269 GB2017051269W WO2017194917A1 WO 2017194917 A1 WO2017194917 A1 WO 2017194917A1 GB 2017051269 W GB2017051269 W GB 2017051269W WO 2017194917 A1 WO2017194917 A1 WO 2017194917A1
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Prior art keywords
thin film
otft
phase
film transistor
organic semiconductor
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PCT/GB2017/051269
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English (en)
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Richard Wilson
James Morey
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Sumitomo Chemical Company Limited
Cambridge Display Technology Limited
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Publication of WO2017194917A1 publication Critical patent/WO2017194917A1/fr

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    • 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]
    • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • 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]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • 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]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • H10K10/488—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising a layer of composite material having interpenetrating or embedded materials, e.g. a mixture of donor and acceptor moieties, that form a bulk heterojunction
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass

Definitions

  • This invention relates to organic thin-film transistors (OTFTs), wherein charge carrier mobility is improved by effecting vertical phase separation to form a phase- separated thin film comprising an organic semiconductor phase and a fluoropolymer phase.
  • the present invention relates to a method of manufacturing the aforementioned OTFTs and to biosensors comprising the same.
  • OTFTs Organic thin-film transistors
  • OTFTs are an excellent alternative for use in sensing applications, where there is a demand on inexpensive, disposable devices that provide accurate measurements.
  • biosensor applications are of particular interest.
  • a vast number OTFT-based sensor device architectures employ a configuration, wherein an organic semiconductor with a high carrier mobility is deposited close to the gate/channel area, and which further require a top coat layer of a polymer for device encapsulation and to allow attachment of a sensing element for ions or biomolecules, for example.
  • a top coat layer of a polymer for device encapsulation and to allow attachment of a sensing element for ions or biomolecules, for example.
  • phase-separated organic semiconductor and insulating layers may be mentioned (see e. g. A. Arias et al. Adv. Mater. 2006, 19, 2900).
  • P3HT polymethylmethacrylate
  • PMMA polymethylmethacrylate
  • the present invention solves these problems by effecting vertical phase separation in a blend comprising an organic semiconductor and fluorinated polymer having a low surface energy and thereby simultaneously depositing organic semiconductor material a top coat layer polymer having favourable hydrophobicity, which allows to produce an organic thin film transistor (OTFT) with excellent carrier mobility.
  • OTFT organic thin film transistor
  • an organic thin film transistor as specified in claims 1 to 9.
  • the present invention relates to an organic thin film transistor (OTFT) comprising: a substrate; a gate electrode formed on the substrate; a gate dielectric on the gate electrode; source and drain electrodes over the gate dielectric with a channel region therebetween; and a phase-separated thin film comprising an organic semiconductor phase and a fluoropolymer phase over at least the channel region formed by vertical phase separation from a blend comprising a small-molecule organic semiconductor and a semiconducting fluorinated polymer.
  • the fluoropolymer is preferably a conjugated semiconducting fluorinated polymer.
  • the present invention relates to methods of manufacturing of said organic thin film transistor (OTFT), and to sensing devices (such as e.g. biosensors) comprising the same.
  • OTFT organic thin film transistor
  • sensing devices such as e.g. biosensors
  • the present invention relates to the use of a blend solution comprising a small-molecule organic semiconductor and a fluorinated polymer to promote vertical phase separation during manufacture of an organic thin film transistor (OTFT).
  • OTFT organic thin film transistor
  • OFT organic thin film transistor
  • WO2015/133376 and WO2010/015833 disclose OTFTs formed by phase separation of a liquid comprising a polymer and an organic semiconductor, but in these cases the polymer is an electrical insulator, is not a conjugated polymer, and the polymer does not comprise an active semiconductive part of the device after phase separation.
  • the fluorinated polymer is semiconductive and comprises an active semiconductive part of the device.
  • FIG. 1 schematically illustrates the general architecture of an exemplary bottom- gate OTFT according to the present invention.
  • FIG. 2 schematically shows the configuration of the bottom-gate OTFT as used in the examples of the invention.
  • FIG. 3 shows the transfer characteristics of OTFTs using a non-fluorinated host polymer.
  • FIG. 4 shows the transfer characteristics of OTFTs using a fluorinated host polymer according to the present invention.
  • the present invention relates to the use of a blend solution comprising a small-molecule organic semiconductor and a fluorinated polymer to promote vertical phase separation during the manufacture of a bottom-gate organic thin film transistor (OTFT).
  • OTFT organic thin film transistor
  • vertical phase separation describes the phenomenon that a blend comprising at least two different materials, usually in a solvent, changes from one mixed phase to two individual phases during processing (e.g. evaporation of solvent), so that the resulting separated phases are parallel to the surface of the substrate on which the blend is deposited. It is to be noted that in phase-separated thin film, regions may be present at the interface between the phases wherein both phases coexist, e.g. a region with a phase gradient morphology.
  • organic thin film transistors prepared accordingly not only allow the provision of two distinct phases in one single step and thereby simplify their manufacturing process, but that their charge carrier mobility may also be surprisingly enhanced.
  • the use according to the present invention enables to provide the combination of an organic semiconductor layer and a polymer layer having low surface energy in a simple manner. Further details on the use according to the present invention will be described below with respect to the embodiments related to the organic thin film transistor (OTFT) and its manufacturing methods.
  • an organic thin film transistor comprises: a substrate; a gate electrode formed on the substrate; a gate dielectric on the gate electrode; source and drain electrodes over the gate dielectric with a channel region therebetween; and a phase-separated thin film comprising an organic semiconductor phase and a fluoropolymer phase over at least the channel region formed by vertical phase separation from a blend comprising a small-molecule organic semiconductor and a fluorinated polymer.
  • the organic thin film transistor exhibits a bottom-gate configuration, an example of which is shown in Fig. 1.
  • the structure comprises a gate electrode (2) deposited on a substrate (1) with a gate dielectric/insulating layer (3) provided thereover.
  • Source and drain electrodes (4) and (5) are deposited on the gate dielectric (3) and spaced apart from each other to form a channel region (6) therebetween over the gate electrode (2).
  • a phase-separated thin film (7) comprising a fluoropolymer phase (7a) and an organic semiconductor phase (7b) is provided over at least the channel region (6) and may extend over a portion of the source and drain electrodes (4) and (5), with the organic semiconductor phase (7b) being preferably provided in contact therewith.
  • the fluoropolymer phase (7a) may serve as the polymer top coat layer at the air interface. Thereby, a surface layer with low surface energy is provided, which is particularly advantageous when the layer is exposed to an aqueous environment (e.g. in sensor applications).
  • additional layers may be provided on top of the fluoropolymer phase (7a) or the phase may be modified by attaching sensing elements (e.g. ions, specific biomolecules) on its upper surface.
  • the OTFT according to the present invention is a single-gate OTFT, as opposed to double-gate OTFTs.
  • the surface energy of the fluorinated polymer is lower than that of the small-molecule organic semiconductor.
  • the surface energy may be quantified (in mN-rrv 1 ) by conventional methods known in the art, e.g. by measuring the contact angle of a drop of liquid placed on the surface of the inspected object and calculating the surface energy from the contact angle based on Young's equation.
  • the fluorinated polymer has preferably a fluorine content of at least 10 wt.-%, more preferably at least 20 wt.-%, especially preferably at least 30 wt.-%, based on the total weight of the fluorinated polymer.
  • the fluorinated polymer is a conjugated polymer, which may contribute to the charge transport within the OTFT.
  • the fluorinated polymer is a conjugated polymer comprising alternating single and double bonds or aromatic units along the polymer chain and pendant fluorinated side groups. While not being limited thereto, polymers comprising fluorenyl repeating units according to General Formula (I) may be mentioned as examples:
  • R', R", R'" and R" independently represent a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C6-C60 heteroaryl group; n and m are independently 0 to 3; and at least one of R', R", R'" and R"" - preferably R' or R" or both R' and R" - represents a fluorinated alkyl group or comprises the same as a substituent.
  • the fluorinated alkyl group may have the formulae F 2 HC-(CF2)p-, F3C-(CF2) P -, or H 3 C-(CF 2 ) P -, with p being 2 to 30, in embodiments 3 to 15.
  • the fluorinated polymer may be exclusively derived from fluorinated monomers or may be a co-polymer formed from a single or multiple different fluorinated monomers and a single or multiple different non-fluorinated monomers. If the fluorinated polymer is a copolymer comprising fluorinated and non-fluorinated repeating units, it is preferable that the content of fluorinated repeating units is 10 to 99 mol-%, more preferably 25 to 99 mol%, further preferably 35 to 99 mol-%, based on the total content of repeating units.
  • the small-molecule organic semiconductor may be appropriately chosen by the skilled artisan from known materials, including soluble derivatives of acenes such as tetracene, chrysene, pentacene, pyrene, perylene, coronene, benzodithiophene, anthradithiophene, and other condensed aromatic and hetero-aromatic hydrocarbons; and soluble, suitably substituted, aniline-, thiophene-, pyrrole-, furan-, or pyridine-based oligomers.
  • soluble derivatives of acenes such as tetracene, chrysene, pentacene, pyrene, perylene, coronene, benzodithiophene, anthradithiophene, and other condensed aromatic and hetero-aromatic hydrocarbons
  • the small- molecule organic semiconductor is a heteroacene derivative, preferably a thiophene- based derivative comprising linear or branched C3-C30 alkyl groups, preferably linear C3- C30 alkyl groups.
  • the substrate may generally be rigid or flexible, the substrate material being usually selected from glass, silicon, and plastics (such as poly(ethylene terephthalate) (PET), poly(ethylene-naphthalate) (PEN), polycarbonate and polyimide, for example).
  • PET poly(ethylene terephthalate)
  • PEN poly(ethylene-naphthalate)
  • polycarbonate polycarbonate
  • polyimide polyimide
  • the source and drain electrodes may be made of materials suitably selected by the skilled artisan.
  • the source and drain electrodes comprise a high workfunction material, preferably a metal, with a workfunction of greater than 3.5 eV, for example gold, platinum, palladium, molybdenum, tungsten, or chromium. More preferably, the metal has a workfunction in the range of from 4.5 to 5.5 eV.
  • Metal alloys and oxides e.g. molybdenum trioxide and indium tin oxide
  • conductive polymers may be deposited as the source and drain electrodes.
  • the source and drain electrodes preferably comprise either a metal having a workfunction of less than 3.5 eV such as calcium or barium or a thin layer of metal compound, in particular an oxide or fluoride of an alkali or alkali earth metal for example lithium fluoride, barium fluoride and barium oxide, or conductive polymers. While the source and drain electrodes may be preferably formed from the same material for ease of manufacture, it is also possible that the source and drain electrodes may be formed of different materials for optimization of charge injection and extraction respectively.
  • a metal having a workfunction of less than 3.5 eV such as calcium or barium or a thin layer of metal compound, in particular an oxide or fluoride of an alkali or alkali earth metal for example lithium fluoride, barium fluoride and barium oxide, or conductive polymers. While the source and drain electrodes may be preferably formed from the same material for ease of manufacture, it is also possible that the source and drain electrodes may be formed of different materials for optimization of charge injection and extraction respectively.
  • the length of the channel defined between the source and drain electrodes may be up to 800 ⁇ , but preferably the length is less than 500 ⁇ .
  • a wide range of conducting materials may be used for the preparation of the gate electrode, e.g. metals (e.g. aluminum or gold) or metal compounds (e.g. indium tin oxide).
  • metals e.g. aluminum or gold
  • metal compounds e.g. indium tin oxide
  • conductive polymers may be deposited as the gate electrode.
  • the thicknesses of the gate electrode, source and drain electrodes may be in the region of 1 to 250 nm, preferably from 2 to 100 nm, as measured by Atomic Force Microscopy (AFM), for example.
  • AFM Atomic Force Microscopy
  • the gate dielectric may be formed by depositing dielectric material which may be suitably selected by the skilled artisan.
  • Organic or inorganic electrically insulating material may be used as gate dielectric material, with polymeric material (polyvinylidenefluoride (PVDF), cyanocelluloses, polyimides, epoxies, etc.) and strontiates, tantalates, titanates, zirconates, aluminum oxides, silicon oxides, tantalum oxides, titanium oxides, silicon nitrides, barium titanate, barium strontium titanate, barium zirconate titanate, zinc selenide, and zinc sulfide being mentioned as examples.
  • PVDF polyvinylidenefluoride
  • cyanocelluloses polyimides
  • epoxies etc.
  • strontiates tantalates, titanates, zirconates, aluminum oxides, silicon oxides, tantalum oxides, titanium oxides, silicon nitrides, barium titanate, barium stront
  • alloys, combinations, and multilayers of these can be used for the gate dielectric.
  • these materials aluminum oxides, silicon oxides, silicon nitrides, and zinc selenide are preferred.
  • the gate dielectric can be deposited in the OTFT as a separate layer, or alternatively, if the gate electrode is made of a oxidizable metal (e.g. Al), the gate dielectric layer may be formed on the gate electrode by oxidation of the metal surface to the respective metal oxide (e.g. AI2O 3 ), e.g. via O2 plasma processes.
  • a self-assembled monolayer or other surface treatment is applied on the gate dielectric at the channel region to improve the charge carrier mobility and the on/off ratio of the OTFT, to promote crystallinity, to reduce contact resistance, to repair surface characteristics and to promote adhesion where required.
  • a first self-assembled monolayer is deposited on the gate dielectric on at least part of the surface of the channel region on which the phase-separated thin film is formed.
  • the self-assembled monolayer decreases the surface energy of the substrate onto which the organic semiconductor is deposited.
  • the surface may be altered from hydrophilic to hydrophobic.
  • the organic semiconductor can form an organized or patterned structure (e.g. lamellar structure) more uniformly when compared to the deposition on a higher surface energy substrate, which may lead to an improvement in ⁇ - ⁇ interactions between the neighbouring polymer chains or small molecules/oligomers, which in turn leads to an improvement in the field effect mobility of the transistor.
  • the charge carrier transport in the horizontal axis across the channel region is favoured.
  • the source electrode and/or drain electrode comprise(s) a second self-assembled monolayer on at least a part of a surface thereof, and the phase- separated thin film is formed in contact with said surface. More preferably, both source electrode and the drain electrode comprise a self-assembled monolayer which may be the same or different. By using such a configuration, the average saturation charge carrier mobility may be further improved.
  • the provision of a first and/or second self-assembled monolayer has the advantage that vertical phase separation between the fluoropolymer phase and the organic semiconductor phase is enhanced.
  • the type of self-assembled monolayers used for the first and second self- assembled monolayers is not particularly limited as long as the surface energy of the substrate surface is decreased. While not being limited thereto, examples of suitable self- assembled layers and their preparation are disclosed in WO 2010/015833 A1 and in DiBenedetto et al., Adv. Mater. 2009, 21 , 1407-1433.
  • octadecyltrichlorosilane ODTS
  • the choice of materials for the second self-assembled monolayer is wider than that for the first self-assembled monolayer as the vertical phase separation and interaction with the organic semiconductor layer over the source and drain electrodes is less critical than over the channel region.
  • Preferred materials for use as the second self-assembled monolayer include thiols (such as alkyl thiols, functionalized thiols, dithiols, ring thiols), one prominent example being pentafluorobenzene thiol (PFB thiol).
  • thiols such as alkyl thiols, functionalized thiols, dithiols, ring thiols
  • PFB thiol pentafluorobenzene thiol
  • the present invention relates to a method of manufacturing an organic thin film transistor (OTFT) comprising: preparing a substrate; forming a gate electrode on the substrate; providing a gate dielectric on the gate electrode; disposing source and drain electrodes over the gate dielectric with a channel region therebetween; and forming a phase-separated thin film comprising an organic semiconductor phase and a fluoropolymer phase over at least the channel region by vertical phase separation using depositing a blend solution comprising a small-molecule organic semiconductor and a fluorinated polymer. Details regarding the preferred embodiments of each of the components correspond to those outlined above with respect to the embodiment related to the OTFT.
  • the method according to the present invention has the advantage that it enables to provide the combination of an organic semiconductor layer and a polymer layer having low surface energy in one single step and thereby simplifies the OTFT manufacturing process, without the difficulties conventionally observed when combining fluorous polymers with dissimilar non-fluorinated materials. Moreover, the method ensures that the organic semiconductor layer is provided in the desired location in the OTFT layer stack, thereby enhancing the carrier mobility.
  • each of the gate, source and drain electrodes, the gate dielectric, and the optional first and second self-assembled monolayers present in the OTFT according to the present invention is not particularly limited to specific techniques and may be suitably chosen by the skilled artisan depending on the material to be deposited. While not being limited thereto, exemplary coating and deposition techniques include thermal deposition, vacuum deposition, laser deposition, screen printing, printing, imprinting, spin casting, dipping, ink-jetting, roll coating, flow coating, drop casting, spray coating, and/or roll printing.
  • the blend solution of organic semiconductor and fluorinated polymer should be formed at a weight ratio adequate for the phase separation.
  • the weight ratio of the fluorinated polymer and the organic semiconductor may be set in the range of from about 1 :99 to about 99: 1 , preferably in the range of from about 1 :50 to 99: 1 in view of the reduction of manufacturing costs.
  • the solvent should be appropriately chosen so as to be capable of simultaneously dissolving the organic semiconductor and the fluorinated polymer, the typical amount of solvent used being in the range of 0.1 to 20 wt % based on the total weight of the blend solution.
  • An annealing step as described in the method of US 8,828,793 B2 may be performed in order to further increase the degree of vertical phase separation and/or to increase the crystallinity of the organic semiconductor phase.
  • the OTFTs according to the present invention may be used in various electronic devices including flat panel displays, photovoltaic devices and sensors.
  • the present invention relates to a sensing device comprising the above-described OTFT, preferably a biosensor.
  • the fluoropolymer phase exhibiting a favorably low surface energy and high hydrophobicity may form the surface exposed to the material to be detected, the applicability particularly in aqueous environments may be widened.
  • OTFT devices having the configuration illustrated in Fig. 2 have been prepared as testing devices, using a substrate (11) made of glass, onto which a gate electrode (12) made of aluminum has been deposited, with AI2O3 serving as the gate dielectric/insulating layer (13).
  • AI2O3 serving as the gate dielectric/insulating layer (13).
  • Au was deposited on the gate dielectric (13) so as to form a channel region therebetween over the gate electrode (12).
  • Contacts (16a and 16b) made of silver were provided on each side of the OTFT.
  • a first self-assembled monolayer (18c) was provided in the channel region by using octadecyltrichlorosilane (ODTS) and second self-assembled monolayers (18a and 18b) were provided on the source and drain electrodes (14) by using pentafluorobenzene thiol (PFB thiol). Thereafter, a substance selected from the materials shown in Tab. 1 have been deposited on the resulting structures, with FP1 denoting a co-polymer comprising the monomer units (A) and (B) (1 : 1), FP2 being a co-polymer comprising the monomer units (A) and (C) (1 : 1), and OSC1 denoting a small-molecule organic semiconductor (D),
  • ODTS octadecyltrichlorosilane
  • PFB thiol pentafluorobenzene thiol
  • Deposition of the materials was accomplished by spin-coating solutions using trifluorotoluene (FP1), xylene (FP2, OSC1 , FP2-OSC1), or xylene/trifluorotoluene (FP1- OSC1) as solvents (0.9% w/v in case of FP1-OSC1 , 1.2% w/v in all other cases).
  • FP1- OSC1 trifluorotoluene
  • solvents 0.9% w/v in case of FP1-OSC1 , 1.2% w/v in all other cases.
  • the transfer characteristics of OTFT devices having the same configuration as the above testing devices have been studied, wherein in one OTFT, the layer comprising organic semiconductor (17) has been provided by using a blend comprising OSC1 as a small-molecule organic semiconductor and FP1 as a fluorinated polymer, and in the other OTFT, P1 , a non-fluorinated analogue of FP1 , has been used instead of FP1.
  • the transfer performance of OTFTs comprising the fluoropolymer FP1 is shown in Fig. 3.
  • the transfer performance of OTFTs comprising the non-fluorinated analogue P1 is shown in Fig. 4, each in comparison with a control OTFT without OSC1.
  • Figures 3 and 4 demonstrate that carrier mobility is remarkably increased by using a fluorinated polymer in a blend with a small-molecule organic semiconductor, which thus shows that migration of the organic semiconductor OSC1 to the gate/channel region has occurred and a phase-separated thin film has been formed.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Composite Materials (AREA)
  • Thin Film Transistor (AREA)

Abstract

La présente invention concerne la réalisation d'une séparation de phase verticale dans un mélange comprenant un semi-conducteur organique et un polymère fluoré semi-conducteur ayant une faible énergie de surface et ainsi le dépôt simultané d'un matériau semi-conducteur organique et d'un polymère de couche de revêtement supérieur ayant une hydrophobicité favorable, ce qui permet de produire des transistors à couches minces organiques (OTFT) avec une mobilité de porteur de charge améliorée d'une manière simple.
PCT/GB2017/051269 2016-05-10 2017-05-08 Séparation de phase pour une mobilité de porteuse améliorée dans des dispositifs de transistor à couches minces organique WO2017194917A1 (fr)

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GB201900834D0 (en) * 2019-01-21 2019-03-13 Sumitomo Chemical Co Organic thin film transistor gas sensor

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