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WO2014136436A1 - Transistor à film mince organique et procédé de fabrication dudit transistor - Google Patents

Transistor à film mince organique et procédé de fabrication dudit transistor Download PDF

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Publication number
WO2014136436A1
WO2014136436A1 PCT/JP2014/001176 JP2014001176W WO2014136436A1 WO 2014136436 A1 WO2014136436 A1 WO 2014136436A1 JP 2014001176 W JP2014001176 W JP 2014001176W WO 2014136436 A1 WO2014136436 A1 WO 2014136436A1
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Prior art keywords
organic semiconductor
film transistor
organic
thin film
organic thin
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PCT/JP2014/001176
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English (en)
Japanese (ja)
Inventor
栗原　直樹
聡 蜂屋
恒太 寺井
篤史 八百
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出光興産株式会社
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    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes

Definitions

  • the present invention relates to an organic thin film transistor.
  • Thin film transistors are widely used as display switching elements for liquid crystal display devices and the like.
  • a typical TFT has a gate electrode, an insulator layer, and a semiconductor layer in this order on a substrate, and has a source electrode and a drain electrode formed on the semiconductor layer at a predetermined interval.
  • a semiconductor layer forms a channel region, and an on / off operation is performed by controlling a current flowing between the source electrode and the drain electrode with a voltage applied to the gate electrode.
  • this TFT has been manufactured using amorphous or polycrystalline silicon, but a chemical vapor deposition (CVD) apparatus used for manufacturing a TFT using such silicon is very expensive.
  • CVD chemical vapor deposition
  • Increasing the size of a display device or the like using the method has a problem that it involves a significant increase in manufacturing cost.
  • the process of forming amorphous or polycrystalline silicon is performed at a very high temperature, the types of materials that can be used as a substrate are limited, and a lightweight resin substrate cannot be used. It was.
  • TFTs organic TFTs
  • a vacuum deposition method, a coating method, or the like is known. According to these film forming methods, it is possible to increase the size of an electronic device having a large number of TFTs while suppressing an increase in manufacturing cost, and the process temperature required for film formation can be made relatively low. it can.
  • the organic TFT has an advantage that there are few restrictions on the selection of the material used for the substrate, and its practical use is expected, and research reports have been actively made.
  • Patent Document 1 discloses a method for manufacturing a crystalline organic semiconductor film and a thin film transistor.
  • Patent Document 2 discloses an organic crystal structure, an organic transistor, and a method for manufacturing the organic crystal structure.
  • Patent Document 3 discloses a thin film transistor characterized in that the thickness of a semiconductor layer forming a channel portion between a source electrode and a drain electrode is thin at the center of the channel portion and thick at both ends of the channel portion. ing.
  • Patent Document 4 a solution containing an organic semiconducting compound is applied to at least a channel formation region on a substrate and dried so that the film thickness distribution is within 30% of the film thickness at the center of the channel region.
  • a method of manufacturing an organic field effect transistor for forming an organic semiconductor layer is described.
  • Patent Document 5 has a source electrode, a drain electrode, and an organic semiconductor layer formed by an ink jet method for forming a channel portion between the source electrode and the drain electrode on a substrate. Discloses an organic thin film transistor that does not include a midpoint of a line segment that gives the maximum width of the contour of the organic semiconductor layer and that satisfies the predetermined relationship between the maximum width and the channel length.
  • An object of the present invention is to provide an organic thin film transistor with improved mobility.
  • the present inventors have found that in an organic TFT using an organic semiconductor material for the channel portion, the crystal structure of the organic semiconductor material in the channel portion affects the mobility of the TFT.
  • the inventors have found that an organic TFT having high mobility can be obtained when a relatively thin crystal grown in a smooth flat plate exists in the channel portion, and the present invention has been completed.
  • a channel portion made of an organic semiconductor layer containing an organic semiconductor material between a source electrode and a drain electrode, and the channel portion has an average surface roughness Ra of 5 ⁇ m square of 2 nm or less.
  • an organic thin film transistor containing a flat organic semiconductor crystal wherein the thickness of the flat organic semiconductor crystal is 40 nm or less.
  • an organic thin film transistor with improved mobility can be provided.
  • FIG. 2 is an example of a film thickness measurement result of an organic semiconductor layer of an organic thin film transistor fabricated in Example 1.
  • FIG. FIG. 10 is an enlarged view of FIG. 9.
  • 3 is a measurement result of average surface roughness (Ra) in a 5 ⁇ m square image of a channel portion of the organic thin film transistor manufactured in Example 1. It is a figure which shows the relationship between the gate voltage of the organic thin-film transistor produced in Example 2, and drain current.
  • 4 is a polarization micrograph of an organic semiconductor layer of an organic thin film transistor produced in Example 2. It is an example of the film thickness measurement result of the organic-semiconductor layer of the organic thin-film transistor produced in Example 2.
  • FIG. 3 is a measurement result of average surface roughness (Ra) in a 5 ⁇ m square image of a channel portion of an organic thin film transistor manufactured in Example 2. It is a figure which shows the relationship between the gate voltage of the organic thin-film transistor produced in Example 3, and drain current.
  • 4 is a polarizing micrograph of an organic semiconductor layer of an organic thin film transistor produced in Example 3. It is a film thickness measurement result of the organic-semiconductor layer of the organic thin-film transistor produced in Example 3.
  • FIG. 6 is an example of a measurement result of average surface roughness (Ra) in a 5 ⁇ m square image of a channel portion of an organic thin film transistor manufactured in Example 3.
  • FIG. 1 It is a figure which shows the relationship between the gate voltage and drain current of the organic thin-film transistor produced by the comparative example 1.
  • 2 is a polarization micrograph of an organic semiconductor layer of an organic thin film transistor produced in Comparative Example 1. It is an example of the film thickness measurement result of the organic-semiconductor layer of the organic thin-film transistor produced by the comparative example 1.
  • 3 is a measurement result of average surface roughness (Ra) in a 5 ⁇ m square image of a channel portion of an organic thin film transistor manufactured in Comparative Example 1.
  • An organic thin film transistor includes an organic semiconductor layer containing an organic semiconductor material between a source electrode and a drain electrode, for example, a gap between the source electrode and the drain electrode, and an upper surface portion or a lower surface portion of the gap.
  • the channel portion contains a flat organic semiconductor crystal having an average surface roughness Ra of 5 ⁇ m square of 2 nm or less, and the film thickness of the flat organic semiconductor crystal is 40 nm or less.
  • the channel portion is a region sandwiched between the source electrode and the drain electrode in the semiconductor facing the gate insulating film and facing the gate electrode, and has the thickness of the semiconductor. More specifically, the region range is defined by the thickness of the semiconductor film, the channel length (the distance between the source electrode and the drain electrode), and the channel width (the width between the source electrode and the drain electrode).
  • FIG. 1 to FIG. 4 are diagrams showing examples of the element configuration of an organic thin film transistor according to an embodiment of the present invention.
  • the organic thin film transistor 1 of FIG. 1 has a source electrode 11 and a drain electrode 12 formed on a substrate 10 so as to face each other with a predetermined interval. And the organic-semiconductor layer 13 is formed so that the source electrode 11, the drain electrode 12, and the gap
  • a gate electrode 15 is formed on the insulator layer 14 and on the gap between the source electrode 11 and the drain electrode 12. In the organic thin film transistor 1, the channel portion is a region indicated by 13a in the figure.
  • the organic thin film transistor 2 in FIG. 2 has a gate electrode 15 and an insulator layer 14 in this order on a substrate 10, and a pair of source electrode 11 and drain formed on the insulator layer 14 with a predetermined interval therebetween.
  • An electrode 12 is provided, and an organic semiconductor layer 13 is formed thereon.
  • the region 13 a of the organic semiconductor layer 13 forms a channel portion, and is turned on / off by controlling the current flowing between the source electrode 11 and the drain electrode 12 with the voltage applied to the gate electrode 15.
  • the organic thin film transistor 3 in FIG. 3 has a gate electrode 15, an insulator layer 14, and an organic semiconductor layer 13 in this order on a substrate 10.
  • a source electrode 11 and a drain electrode 12 are provided.
  • a region 13a of the organic semiconductor layer 13 is a channel portion.
  • a region 13a of the organic semiconductor layer 13 is a channel portion.
  • the organic thin film transistor has a field effect transistor (FET) structure. As described above, there are several configurations depending on the position of the electrodes, the layer stacking order, and the like.
  • An organic thin film transistor is formed with a predetermined distance from an organic semiconductor layer (organic compound layer), a source electrode and a drain electrode that are formed to face each other with a predetermined space therebetween, and a source electrode and a drain electrode. And a current flowing between the source and drain electrodes is controlled by applying a voltage to the gate electrode.
  • FET field effect transistor
  • the distance between the source electrode and the drain electrode is determined depending on the use of the organic thin film transistor of the present invention, and is usually 0.1 ⁇ m to 1 mm, preferably 1 ⁇ m to 100 ⁇ m, more preferably 2 ⁇ m to 100 ⁇ m, and further preferably 2 to 60 ⁇ m. It is.
  • the channel portion includes a flat organic semiconductor crystal having an average surface roughness Ra of 5 ⁇ m square of 2 nm or less, and the thickness of the flat organic semiconductor crystal is 40 nm or less.
  • the thickness of the flat organic semiconductor crystal is preferably 20 nm or less, more preferably 0.5 nm to 20 nm, more preferably 2 nm to 20 nm, and even more preferably 10 nm to 20 nm.
  • the flat organic semiconductor crystal is a crystal in a channel portion and including a region having an average surface roughness Ra of 2 nm or less in a range of 5 ⁇ m ⁇ 5 ⁇ m.
  • the flat organic semiconductor crystal preferably includes a region having an average surface roughness Ra of 5 ⁇ m square of 1 nm or less.
  • SAICAS Surface And Interfacial Cutting Analysis System
  • FIB Focused Ion Beam
  • the average roughness can be measured by observing the cross section using an electron microscope or an atomic force microscope. Since the information obtained in this way is one-dimensional information, the surface information can be obtained by further cutting after the measurement to expose a new cross section and repeating the measurement.
  • the thickness (Tp) of the flat crystal is defined as the film thickness of a region having an average surface roughness Ra of 2 nm or less in a range of 5 ⁇ m ⁇ 5 ⁇ m. In this embodiment, it is preferable that the thickness change of the channel portion is within 175% of the thickness of the flat organic semiconductor crystal.
  • the maximum film thickness of the channel part is preferably 110 nm or less, and more preferably 55 nm or less.
  • the difference between the maximum film thickness (Tm) of the channel portion and the film thickness (Tp) of the plate crystal and the ratio of Tp [(Tm ⁇ Tp) ⁇ 100 / Tp):%] is defined as a change in film thickness. To do. In the channel portion, the film thickness of each plate-like crystal hardly changes and is smooth, but the plate-like crystal may overlap in a step shape and / or a terrace shape. Therefore, the film thickness may change as described above for the entire channel portion.
  • organic thin film transistors In addition to the element configurations of the organic thin film transistors 1 to 4, various configurations of organic thin film transistors have been proposed as organic thin film transistors.
  • the device configuration is not limited to these devices as long as the current flowing between the source electrode and the drain electrode is controlled by the voltage applied to the gate electrode so that an effect such as on / off operation or amplification is realized. Absent.
  • the top-and-bottom contact organic thin-film transistor proposed by Yoshida et al. Of the National Institute of Advanced Industrial Science and Technology in the 49th Conference on Applied Physics Related Lectures 27a-M-3 (March 2002) (see Fig. 5)
  • a vertical organic thin film transistor (see FIG. 6) proposed by Kudo et al. Of Chiba University in IEEJ Transactions 118-A (1998) 1440.
  • the organic semiconductor layer forming the channel portion which is a characteristic portion of the organic thin film transistor according to the embodiment of the present invention, is, for example, a position where a liquid containing an organic semiconductor material (hereinafter referred to as an organic semiconductor composition) becomes a channel portion.
  • the film can be formed by a film forming method having a step of attaching to the substrate and a step of removing the solvent from the attached composition liquid and growing a plate crystal.
  • the organic semiconductor composition contains a solvent and an organic semiconductor material.
  • the solvent used in the organic semiconductor composition include aromatic alkoxy groups such as 4-methoxytoluene, 1,2-dimethoxybenzene, anisole, phenetole, and anethole; aromatic alkanes such as phenylcyclohexane, tetralin, xylene, mesitylene, and ethylbenzene. And halogenated aromatic compounds such as o-dichlorobenzene and monochlorobenzene. Anisole or tetralin is preferred. These solvents may be used alone or in combination of two or more.
  • a known organic semiconductor material can be used as the organic semiconductor material.
  • ⁇ -conjugated polymers such as polypyrroles, polythiophenes, polyanilines, polyallylamines, fluorenes, polycarbazoles, polyindoles, poly (P-phenylene vinylene) s, and the like can be used.
  • low-molecular substances having solubility in solvents for example, polycyclic aromatic derivatives such as pentacene, phthalocyanine derivatives, perylene derivatives, tetrathiafulvalene derivatives, sulfur-containing heterocyclic compounds (for example, Benzothieno-benzothiophene (BTBT) ), 5,11-Bis (triethylsilylethynyl) anthra [2,3-b: 6,7-b '] dithiophene (TES-ADT, etc.), oxygen-containing heterocyclic compounds, nitrogen-containing heterocyclic compounds (carbazole, etc.) , Tetracyanoquinodimethane derivatives, fullerenes, carbon nanotubes, and the like can be used.
  • polycyclic aromatic derivatives such as pentacene, phthalocyanine derivatives, perylene derivatives, tetrathiafulvalene derivatives, sulfur-containing heterocyclic compounds (for example, Benzothieno
  • binder resin polystyrene, acrylic resin, polycarbonate, polydimethylsiloxane, nylon, polyimide, cyclic olefin copolymer, epoxy polymer, cellulose, polyoxymethylene, polyolefin polymer, polyvinyl polymer, polyester polymer, polyether polymer Polyamide polymers, fluorine polymers, biodegradable plastics, phenol resins, amino resins, unsaturated polyester resins, diallyl phthalate resins, polyurethane resins, silicone resins, and copolymers combining various polymers are used.
  • polystyrene poly ⁇ -methylstyrene or poly-2-vinylnaphthalene having a weight average molecular weight of 10,000 or less.
  • organic semiconductor polymers or conductive polymers may be used.
  • Examples of the surfactant include fatty acids.
  • Examples of the rheology control agent include inorganic fine particles.
  • the concentration of the binder resin is preferably 0.05 to 2.0% by mass, and particularly preferably 0.1 to 1.0% by mass.
  • the concentration of the surfactant is preferably 0.01 to 0.2% by mass, and particularly preferably 0.03 to 0.1% by mass.
  • the concentration of the rheology control agent is preferably 0.01 to 3% by mass, and particularly preferably 0.05 to 2% by mass.
  • an organic semiconductor composition containing the following components (A) to (C).
  • the composition may contain the above-described binder resin, surfactant, rheology control agent, and the like as necessary.
  • the organic semiconductor material of the above component (C) exhibits excellent performance such as high mobility, but has a problem in solubility. About this problem, it discovered that an organic-semiconductor material could be dissolved with sufficient density
  • the aliphatic group-substituted aromatic solvent of component (A) is the main solvent of the organic semiconductor composition.
  • the aliphatic group which is a substituent For example, a linear alkyl group, a branched alkyl group, a cyclic alkyl group etc. are mentioned.
  • the aliphatic ring which shares one side of an aromatic ring may be sufficient. Since the solubility of the organic semiconductor material is good, the total number of carbon atoms of the aliphatic group is preferably 6 or less.
  • Examples of the aliphatic group-substituted aromatic solvent include toluene, xylene, mesitylene, 1,2,4-trimethylbenzene, ethylbenzene, indene, indane, tetralin, and 1-methylnaphthalene, preferably mesitylene, 1, Examples include 2,4-trimethylbenzene and tetralin. These solvents may be used alone or in combination of two or more.
  • the mass ratio of the aliphatic group-substituted aromatic solvent is preferably 55 to 95%, more preferably 60 to 90% of the entire organic semiconductor composition. If it is from 55 to 95%, the harmony with the component (B) is good, and the solubility of the organic semiconductor material tends to be improved.
  • the N, N-substituted amide solvent of component (B) is a sub-solvent for the organic semiconductor composition.
  • a substituent on one nitrogen may be bonded to another site in one molecule to form a ring structure.
  • limiting in particular about a substituent As for the sum total of the number of elements except the hydrogen atom of the substituent on at least one nitrogen, 3 or less are preferable. If it is 3 or less, the solvation to an organic-semiconductor material is easy, and the solubility of an organic-semiconductor material improves.
  • the mass ratio of the component (B) is preferably 3 to 43%, more preferably 10 to 40% of the whole organic semiconductor solution of the present invention.
  • the mass ratio is 3 to 43%, the harmony with the component (A) is good and the solubility of the organic semiconductor material is likely to be improved.
  • an organic semiconductor material having a heteroaromatic ring for example, furan or thiophene
  • a benzene ring and having a condensed ring composed of 5 or more rings
  • the oligomer and polymer organic-semiconductor material containing multiple said 5 or more condensed rings can also be used.
  • the upper limit of the number of rings in the condensed ring structure portion is not particularly limited, but is, for example, 10 rings or less, 7 rings or less, or 6 rings or less.
  • the heteroaromatic ring preferably contains a sulfur atom or an oxygen atom, and particularly, the condensed ring compound preferably has a dibenzothiophene skeleton or a dibenzofuran skeleton.
  • the condensed ring portion having 5 or more rings having a heteroaromatic ring and a benzene ring are shown below. These may have a substituent such as a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic group.
  • WO2012 / 090462, JP-A-2009-267140, and WO2011 / 072232 can be referred to.
  • the mass ratio of the component (C) is preferably 0.05 to 0.5%, more preferably 0.08 to 0.3% of the whole organic semiconductor solution of the present invention, although it depends on the film forming method.
  • the low concentration of organic semiconductor material allows the organic semiconductor composition liquid to deposit on the substrate, so that crystals do not precipitate in the composition liquid, and crystals grow from the substrate, forming thin flat crystals. Therefore, it is possible to form a film with little change in film thickness.
  • the component (D) is not particularly limited as long as it does not impair the effects of the component (A) and the component (B), but an aliphatic solvent is preferable.
  • an aliphatic solvent is preferable.
  • the reason is that many organic semiconductor materials have a hydrocarbon chain in addition to the condensed ring portion described so far, and aliphatic solvents have a high affinity with the hydrocarbon chain portion.
  • the solvent that can be used as the component (D) include 1,2,4-trimethylcyclohexane, 1,3,5-trimethylcyclohexane, bicyclohexyl, decahydronaphthalene, decane, undecane, dodecane, dodecene, and the like. Includes bicyclohexyl and decahydronaphthalene. These may be used singly or in combination of two or more.
  • the mass ratio of the component (D) is preferably 1 to 20% of the whole organic semiconductor composition, more preferably 5 to 15%.
  • the organic semiconductor composition described above is attached (applied) to the upper portion of the source electrode 11 and the drain electrode 12 and the gap therebetween.
  • a plate printing method such as gravure printing or offset printing
  • a coating method such as a casting method, a spin coating method, or an ink jet method can be applied.
  • the organic semiconductor composition When used as, for example, an organic semiconductor solution for inkjet, it is excellent in ejection performance and thin film formation performance, and therefore can be suitably used for inkjet printing.
  • a flat organic semiconductor crystal can be formed in the channel portion of the organic semiconductor layer by applying the composition with an inkjet printing apparatus.
  • a plate-like crystal is grown from the deposited composition.
  • a film of an organic semiconductor material that is a solute is formed by removing the solvent component described above.
  • protrusions that are crystal aggregates extremely thicker than the plate-like crystals are formed at the outer peripheral portion where the composition first adheres and at the center portion of the composition where the solvent is finally volatilized.
  • a semiconductor crystal is hardly formed (see FIG. 8 described later).
  • the crystal aggregate means a structure in which large crystals are discontinuously stacked, unlike a plate-like crystal. Crystal aggregates contribute little to electrical conduction.
  • an annular or island-shaped protrusion can be formed in a region other than the channel portion of the organic semiconductor layer so that it does not exist in the channel portion.
  • the protrusions contain more binder resin than the channel part. Thereby, it is possible to form a flat crystal of an organic semiconductor that does not contain a binder resin in the channel portion.
  • the mass average molecular weight of the binder resin may be adjusted.
  • the content of the binder resin on the film surface can be measured by a surface enhanced Raman scattering method.
  • the organic thin-film transistor of this invention should just have the channel part mentioned above, and can apply a well-known thing about other components, such as an electrode.
  • other components such as an electrode.
  • examples of constituent members of the organic thin film transistor will be described.
  • the organic semiconductor layer in the organic thin film transistor of the present invention is a layer formed by using, for example, the above-described organic semiconductor composition of the present invention.
  • the thickness of the organic semiconductor layer is not particularly limited, but is usually 0.5 nm to 1 ⁇ m, preferably 2 nm to 250 nm.
  • the film thickness of the organic semiconductor layer is the film thickness of the entire film on which the organic semiconductor is formed regardless of the channel portion.
  • the maximum film thickness of the channel portion is preferably 110 nm or less, and more preferably 55 nm or less.
  • the annealing temperature is preferably 50 to 200 ° C., more preferably 70 to 200 ° C.
  • the time is preferably 10 minutes to 12 hours, more preferably 1 hour to 10 hours, and further preferably 30 minutes to 10 hours. .
  • the substrate in the organic thin film transistor of the present invention plays a role of supporting the structure of the organic thin film transistor.
  • a material in addition to glass, inorganic compounds such as metal oxides and nitrides, plastic films (PET, PES, PC) It is also possible to use metal substrates or composites or laminates thereof.
  • PET, PES, PC plastic films
  • metal substrates or composites or laminates thereof when the structure of the organic thin film transistor can be sufficiently supported by the components other than the substrate, it is possible not to use the substrate.
  • a silicon (Si) wafer may be used as a material for the substrate.
  • Si itself can be used as a gate electrode / substrate.
  • the surface of Si can be oxidized to form SiO 2 and used as an insulating layer.
  • a metal layer such as Au may be formed on the Si substrate serving as the substrate and gate electrode as an electrode for connecting the lead wire.
  • the material of the gate electrode, the source electrode and the drain electrode is not particularly limited as long as it is a conductive material.
  • Magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide mixture can be used lithium / aluminum mixtures.
  • Examples of the method for forming the electrode include means such as vapor deposition, electron beam vapor deposition, sputtering, atmospheric pressure plasma method, ion plating, chemical vapor deposition, electrodeposition, electroless plating, spin coating, printing, and ink jet. .
  • a conductive thin film formed using the above method is formed using a known photolithographic method or a lift-off method, on a metal foil such as aluminum or copper.
  • the thickness of the electrode formed in this way is not particularly limited as long as current is conducted, but is preferably in the range of 0.2 nm to 10 ⁇ m, more preferably 4 nm to 300 nm. Within this preferable range, the film thickness is too thin, so that the resistance increases and a voltage drop does not occur. In addition, since the film is not too thick, it does not take time to form the film, and when another layer such as a protective layer or an organic semiconductor layer is laminated, the laminated film can be smooth without causing a step.
  • the source electrode, drain electrode, and gate electrode can be formed using a fluid electrode material such as a solution, paste, ink, or dispersion containing the above-described conductive material.
  • a fluid electrode material containing conductive polymer or metal fine particles containing platinum, gold, silver, or copper is preferable.
  • the solvent or dispersion medium is preferably a solvent or dispersion medium containing 60% by mass or more, preferably 90% by mass or more of water, in order to suppress damage to the organic semiconductor.
  • the dispersion containing the metal fine particles for example, a known conductive paste or the like may be used, but a dispersion containing metal fine particles having a particle size of usually 0.5 nm to 50 nm, 1 nm to 10 nm is preferable.
  • the material of the fine metal particles include platinum, gold, silver, nickel, chromium, copper, iron, tin, antimony, lead, tantalum, indium, palladium, tellurium, rhenium, iridium, aluminum, ruthenium, germanium, molybdenum, Tungsten, zinc, or the like can be used.
  • an electrode using a dispersion in which these metal fine particles are dispersed in water or a dispersion medium which is an arbitrary organic solvent using a dispersion stabilizer mainly composed of an organic material.
  • a method for producing such a dispersion of metal fine particles metal ions can be reduced in the liquid phase, such as a physical generation method such as gas evaporation method, sputtering method, metal vapor synthesis method, colloid method, coprecipitation method, etc.
  • a chemical production method for producing metal fine particles preferably disclosed in JP-A-11-76800, JP-A-11-80647, JP-A-11-319538, JP-A-2000-239853, and the like.
  • metal fine particle dispersions may be directly patterned by an ink jet method, or may be formed from a coating film by lithograph or laser ablation. Moreover, the patterning method by printing methods, such as a letterpress, an intaglio, a lithographic plate, and screen printing, can also be used. After the electrode is formed and the solvent is dried, the metal fine particles are heat-fused by heating in a shape within a range of 100 ° C. to 300 ° C., preferably 150 ° C. to 200 ° C., if necessary. An electrode pattern having the following shape can be formed.
  • a known conductive polymer whose conductivity is improved by doping is also preferable to use as another gate electrode, source electrode, and drain electrode material.
  • conductive polyaniline, conductive polypyrrole, conductive polythiophene ( A complex of polyethylene dioxythiophene and polystyrene sulfonic acid and the like, and a complex of polyethylene dioxythiophene (PEDOT) and polystyrene sulfonic acid are also preferably used. These materials can reduce the contact resistance between the organic semiconductor layer of the source electrode and the drain electrode.
  • These forming methods may also be patterned by an ink jet method, or may be formed from a coating film by lithography, laser ablation, or the like.
  • the patterning method by printing methods such as a letterpress, an intaglio, a lithographic plate, and screen printing, can also be used.
  • a buffer layer may be provided between the organic semiconductor layer and the source and drain electrodes for the purpose of improving the injection efficiency.
  • the buffer layer has an alkali metal or alkaline earth metal ion bond such as LiF, Li 2 O, CsF, NaCO 3 , KCl, MgF 2 , and CaCO 3 used for an organic EL cathode for an n-type organic thin film transistor.
  • Alq alkali metal or alkaline earth metal ion bond
  • cyano compounds such as FeCl 3 , TCNQ, F4-TCNQ, HAT, CFx, GeO 2 , SiO 2 , MoO 3 , V 2 O 5 , VO 2 , V 2 O 3 , MnO, Mn 3 O 4 , ZrO 2 , WO 3 , TiO 2 , In 2 O 3 , ZnO, NiO, HfO 2 , Ta 2 O 5 , ReO 3 , metal oxides other than alkaline earth metals, such as PbO 2 , Inorganic compounds such as ZnS and ZnSe are desirable. In many cases, these oxides cause oxygen vacancies, which are suitable for hole injection. Further, amine compounds such as TPD and NPD, and compounds used as a hole injection layer and a hole transport layer in an organic EL device such as CuPc may be used. Moreover, what consists of two or more types of said compounds is desirable.
  • the buffer layer only needs to be thin between the electrode and the organic semiconductor layer, and the thickness is 0.1 nm to 30 nm, preferably 0.3 nm to 20 nm.
  • the material of the insulator layer in the organic thin film transistor of the present invention is not particularly limited as long as it has electrical insulation and can be formed as a thin film.
  • Metal oxide including silicon oxide
  • metal nitride (Including silicon nitride)
  • polymers low molecular organic molecules, and the like, materials having an electrical resistivity at room temperature of 10 ⁇ cm or more can be used, and an inorganic oxide film having a high relative dielectric constant is particularly preferable.
  • Inorganic oxides include silicon oxide, aluminum oxide, tantalum oxide, titanium oxide, tin oxide, vanadium oxide, barium strontium titanate, barium zirconate titanate, lead zirconate titanate, lead lanthanum titanate, strontium titanate, Barium titanate, barium magnesium fluoride, lanthanum oxide, fluorine oxide, magnesium oxide, bismuth oxide, bismuth titanate, niobium oxide, strontium bismuth titanate, strontium bismuth tantalate, tantalum pentoxide, niobium tantalate Examples thereof include bismuth acid, trioxide yttrium, and combinations thereof, and silicon oxide, aluminum oxide, tantalum oxide, and titanium oxide are preferable.
  • inorganic nitrides such as silicon nitride (Si 3 N 4 , SixNy (x, y> 0)) and aluminum nitride can be suitably used.
  • the insulator layer may be formed of a precursor containing an alkoxide metal, and the insulator layer is formed by coating a solution of the precursor on a substrate, for example, and subjecting the solution to a chemical solution treatment including heat treatment. It is formed.
  • the metal in the alkoxide metal is selected from, for example, a transition metal, a lanthanoid, or a main group element.
  • alkoxide in the alkoxide metal examples include, for example, alcohols including methanol, ethanol, propanol, isopropanol, butanol, isobutanol, methoxyethanol, ethoxyethanol, propoxyethanol, butoxyethanol, pentoxyethanol, heptoxyethanol, Examples thereof include those derived from alkoxy alcohols including methoxypropanol, ethoxypropanol, propoxypropanol, butoxypropanol, pentoxypropanol, heptoxypropanol, and the like.
  • the insulator layer when the insulator layer is made of the above-described material, polarization easily occurs in the insulator layer, and the threshold voltage for transistor operation can be reduced. Further, among the above materials, in particular, when an insulator layer is formed of silicon nitride such as Si 3 N 4 , SixNy, or SiONx (x, y> 0), a depletion layer is more easily generated, and the threshold of transistor operation is increased. The voltage can be further reduced.
  • polyimide, polyamide, polyester, polyacrylate, photo radical polymerization system, photo cation polymerization system photo-curable resin, copolymer containing acrylonitrile component, polyvinyl phenol, polyvinyl alcohol, Polysiloxane, polyurethane, novolac resin, melamine resin, cyanoethyl pullulan, and the like can also be used.
  • a photocurable acrylate is preferable.
  • wax polyethylene, polychloropyrene, polyethylene terephthalate, polyoxymethylene, polyvinyl chloride, polyvinylidene fluoride, polymethyl methacrylate, polysulfone, polycarbonate, polystyrene (PS), polyolefin, polyacrylamide, poly (acrylic acid), resole resin,
  • a polymer material having a high dielectric constant such as pullulan.
  • the organic material may be a fluororesin such as Cytop (registered trademark).
  • the insulator layer may be a mixed layer using a plurality of inorganic or organic compound materials as described above, or may be a laminated structure of these. In this case, the performance of the device can be controlled by mixing or laminating a material having a high dielectric constant and a material having water repellency, if necessary.
  • the insulator layer may include an anodic oxide film or the anodic oxide film as a configuration.
  • the anodized film is preferably sealed.
  • the anodized film is formed by anodizing a metal that can be anodized by a known method. Examples of the metal that can be anodized include aluminum and tantalum, and the anodizing method is not particularly limited, and a known method can be used.
  • An oxide film is formed by anodizing. Any electrolyte solution that can form a porous oxide film can be used as the anodizing treatment. Generally, sulfuric acid, phosphoric acid, oxalic acid, chromic acid, boric acid, sulfamic acid, benzenesulfone, and the like can be used. An acid or the like or a mixed acid obtained by combining two or more of these or a salt thereof is used.
  • the treatment conditions for anodization vary depending on the electrolyte used and cannot be specified in general. In general, however, the concentration of the electrolyte is 1 to 80% by mass, the temperature of the electrolyte is 5 to 70 ° C., and the current density.
  • a preferred anodizing treatment is a method in which an aqueous solution of sulfuric acid, phosphoric acid or boric acid is used as the electrolytic solution and the treatment is performed with a direct current, but an alternating current can also be used.
  • the concentration of these acids is preferably 5 to 45% by mass, and the electrolytic treatment is preferably performed for 20 to 250 seconds at an electrolyte temperature of 20 to 50 ° C. and a current density of 0.5 to 20 A / cm 2 .
  • the thickness of the insulator layer As the thickness of the insulator layer, if the layer is thin, the effective voltage applied to the organic semiconductor increases, so the drive voltage and threshold voltage of the device itself can be lowered, but conversely between the source and gate. Therefore, it is necessary to select an appropriate film thickness, which is normally 10 nm to 5 ⁇ m, preferably 50 nm to 2 ⁇ m, and more preferably 100 nm to 1 ⁇ m.
  • any orientation treatment may be performed between the insulator layer and the organic semiconductor layer.
  • a preferable example thereof is a method for improving the crystallinity of the organic semiconductor layer by reducing the interaction between the insulator layer and the organic semiconductor layer by performing a water repellent treatment or the like on the surface of the insulator layer.
  • Silane coupling agents such as hexamethyldisilazane, octadecyltrichlorosilane, trichloromethylsilazane, and self-organized alignment film materials such as alkane phosphoric acid, alkane sulfonic acid, and alkane carboxylic acid are insulated in a liquid phase or gas phase state.
  • An example is a method in which the film is brought into contact with the surface of the film to form a self-assembled film, followed by appropriate drying treatment.
  • a method in which a film made of polyimide or the like is provided on the surface of the insulating film and the surface is rubbed so as to be used for liquid crystal alignment is also preferable.
  • the insulator layer can be formed by vacuum deposition, molecular beam epitaxy, ion cluster beam, low energy ion beam, ion plating, CVD, sputtering, JP-A-11-61406, 11-133205, JP-A 2000-121804, 2000-147209, 2000-185362, etc., dry process such as atmospheric pressure plasma method, spray coating method, spin coating method, blade coating Examples thereof include wet processes such as a method by coating such as a method, a dip coating method, a cast method, a roll coating method, a bar coating method, and a die coating method, and a patterning method such as printing and ink jetting.
  • the wet process is a method of applying and drying a liquid in which fine particles of inorganic oxide are dispersed in an arbitrary organic solvent or water using a dispersion aid such as a surfactant as required, or an oxide precursor, for example,
  • a so-called sol-gel method in which a solution of an alkoxide body is applied and dried is used.
  • the method for forming the organic thin film transistor of the present invention is not particularly limited and may be a known method.
  • the steps after the formation of the organic semiconductor layer are steps which are not exposed to the atmosphere.
  • some p-type TFT materials are exposed to the atmosphere once, and the performance is improved by adsorbing oxygen or the like. Therefore, depending on the material, the materials are appropriately exposed to the atmosphere.
  • a gas barrier layer may be formed on the whole or a part of the outer peripheral surface of the organic transistor element.
  • the gas barrier layer As a material for forming the gas barrier layer, those commonly used in this field can be used, and examples thereof include polyvinyl alcohol, ethylene-vinyl alcohol copolymer, polyvinyl chloride, polyvinylidene chloride, and polychlorotrifluoroethylene. . Furthermore, the inorganic substance which has the insulation illustrated in the said insulator layer can also be used.
  • an electronic device may be an apparatus using the organic thin film transistor of the present invention, such as a circuit, a personal computer, a display, a mobile phone, an electronic device used for a thin film display, etc.
  • a circuit such as a personal computer, a display, a mobile phone, an electronic device used for a thin film display, etc.
  • These include display electronic devices, wearable electronic devices such as plastic IC cards and information tags, medical devices such as biosensors, and measuring devices.
  • Example 1 Fabrication of gate electrode A glass substrate was ultrasonically cleaned in the order of isopropyl alcohol (IPA), pure water, and IPA for 5 minutes each in these, and then chromium was deposited to a thickness of 50 nm by sputtering. Then, a gate electrode was produced. Next, the substrate was ultrasonically cleaned with IPA for 10 minutes, and then dried by blowing dry N 2 gas.
  • IPA isopropyl alcohol
  • Tricyclodecane dimethanol diacrylate (compound 1 below) represented by the following structural formula 0.6 g (colorless transparent liquid), 0.06 g of benzoin isobutyl ether as a polymerization initiator, solvent
  • a composition 2 g of propylene glycol 1-monomethyl ether 2-acetate (PGMEA) was mixed to obtain a composition for forming an insulating film.
  • PGMEA propylene glycol 1-monomethyl ether 2-acetate
  • composition for forming an insulating film was filtered through a 0.2 micron PTFE membrane filter, then dropped on the substrate in a nitrogen atmosphere, press-coated at 500 rpm for 3 seconds, and then spin-coated at 3000 rpm for 30 seconds. Then, a gate insulator layer having a thickness of 500 nm was formed by exposure to 365 nm ultraviolet light and crosslinking.
  • the source electrode and the drain electrode that are not in contact with each other have a gap (channel length L). It formed so that it might become 50 micrometers. At this time, the source electrode and the drain electrode were formed so that the width (channel width W) was 500 ⁇ m. Then, 0.0274 ml of 4- (trifluoromethyl) benzenethiol (TFMBT) and 200 ml of IPA were mixed and placed in a glass container, and the substrate was immersed in the thiol treatment for 10 minutes to perform thiol treatment.
  • TFMBT 4- (trifluoromethyl) benzenethiol
  • a gate voltage of 0 to ⁇ 30 V is applied to the gate electrode of the obtained organic thin film transistor, a voltage of ⁇ 30 V is applied between the source and the drain to pass a current, and the threshold voltage (Vth) and the field effect mobility ⁇ are evaluated.
  • Vth threshold voltage
  • Application of each voltage and measurement of the current between the source and drain electrodes were performed using a semiconductor characteristic evaluation system (4200SCS manufactured by Keithley Instruments Co., Ltd.). In this case, holes were induced in the channel region (between source and drain) of the organic semiconductor layer, and operated as a p-type transistor.
  • the field effect mobility ⁇ of holes in the current saturation region was calculated from the following formula (A).
  • ID (W / 2L) ⁇ C ⁇ ⁇ (VG-VT) 2 (A) (Where ID is the source-drain current, W is the channel width, L is the channel length, C is the capacitance per unit area of the gate insulator layer, VT is the gate threshold voltage, and VG is the gate voltage.)
  • FIG. 7 is a graph showing the relationship between the gate voltage and the drain current of the organic thin film transistor fabricated in Example 1.
  • FIG. 8 is a polarization micrograph of the organic semiconductor layer of the organic thin film transistor produced in Example 1. From the photograph, it can be confirmed that a substantially circular organic semiconductor layer is formed on the source electrode, the drain electrode, and the gap between them.
  • the thickness of the organic semiconductor layer was measured in the arrow direction shown in FIG. Using a micro shape measuring machine Surfcorder [Kosaka Laboratory: ET 3000], the height on the insulating film was set to a height of 0, and the measurement was performed several times in the above direction.
  • An example of the measurement result is shown in FIGS.
  • FIG. 10 is an enlarged view of FIG. FIG. 9 shows that there are thick portions at both ends of the organic semiconductor layer. This is considered as a protrusion (crystal aggregate) generated by the coffee stain phenomenon. Further, a large crystal aggregate having a thickness of 1 ⁇ m was observed at the center of the layer. As can be seen from FIG.
  • the surface roughness of the portion where the flat organic semiconductor crystal grew was evaluated. Using an atomic force microscope (AFM) [SII Nanotechnology, Inc. SPA-400], the average surface roughness (Ra) in a 5 ⁇ m square image was evaluated. The results are shown in FIG. Ra was 0.88 nm.
  • the average surface roughness Ra is a three-dimensional extension of the centerline average roughness Ra defined in JIS B0601 so that it can be applied to the measurement surface. A value obtained by averaging the absolute values of deviations from the reference surface to the designated surface, and is expressed by the following equation.
  • Example 2 An organic thin film transistor was fabricated and evaluated in the same manner as in Example 1 except that the droplet volume by the ink jet apparatus was changed to 720 pl. As a result, the threshold voltage in the current saturation region was ⁇ 0.3 V, and the field effect mobility ⁇ was 0.40 cm 2 / Vs. The results are shown in Table 1. 12 is a graph showing the relationship between the gate voltage and the drain current of the organic thin film transistor fabricated in Example 2. FIG. FIG. 13 is a polarization micrograph of the organic semiconductor layer of the organic thin film transistor fabricated in Example 2. FIG. 14 is an example of a result obtained by measuring the thickness of the organic semiconductor layer in the arrow direction shown in FIG.
  • FIG. 15 shows the measurement results of the average surface roughness (Ra) of the plate-like crystal part in the channel part of the organic thin film transistor produced in Example 2. From this, Ra was 0.39 nm.
  • Example 3 In the preparation of the organic semiconductor composition, an organic semiconductor material represented by the formula (2), polystyrene having a weight average molecular weight of 2500 as a binder resin, tetralin and N-methylpyrrolidone (NMP) in a mass ratio of 0.2: 0.
  • An organic thin film transistor was fabricated and evaluated in the same manner as in Example 1 except that the ratio was 25: 85: 14.55.
  • the threshold voltage in the current saturation region was ⁇ 2.3 V
  • the field effect mobility ⁇ was 0.24 cm 2 / Vs.
  • FIG. 16 is a diagram showing the relationship between the gate voltage and the drain current of the organic thin film transistor fabricated in Example 3.
  • FIG. 16 is a diagram showing the relationship between the gate voltage and the drain current of the organic thin film transistor fabricated in Example 3.
  • FIG. 17 is a polarization micrograph of the organic semiconductor layer of the organic thin film transistor fabricated in Example 3.
  • FIG. 18 is an example of a result obtained by measuring the thickness of the organic semiconductor layer in the arrow direction shown in FIG. The film thickness of the flat crystal in the channel portion was 13 nm, the film thickness of the channel portion was 18 nm at the maximum, and the film thickness change was 38%.
  • FIG. 19 shows the measurement results of the average surface roughness (Ra) of the plate-like crystal part in the channel part of the organic thin film transistor manufactured in Example 3. From this, Ra was 0.94 nm.
  • Example 4 In the preparation of the organic semiconductor composition, the organic semiconductor material represented by the formula (2), poly ⁇ -methylstyrene having a mass average molecular weight of 700 as a binder resin, tetralin and N-methylpyrrolidone (NMP) in a mass ratio of 0.1. : An organic thin film transistor was prepared and evaluated in the same manner as in Example 1 except that the ratio was set to 0.25: 85: 14.65. As a result, the threshold voltage in the current saturation region was ⁇ 3.9 V, and the field effect mobility ⁇ was 0.38 cm 2 / Vs.
  • NMP N-methylpyrrolidone
  • Example 5 In the preparation of the organic semiconductor composition, an organic semiconductor material represented by the formula (2), poly-2-vinylnaphthalene having a weight average molecular weight of 3500 as a binder resin, tetralin and N-methylpyrrolidone (NMP) in a mass ratio of 0. An organic thin film transistor was prepared and evaluated in the same manner as in Example 1 except that the ratio was set to 0.1: 0.25: 85: 14.65. As a result, the threshold voltage in the current saturation region was ⁇ 4.3 V, and the field effect mobility ⁇ was 0.13 cm 2 / Vs.
  • NMP N-methylpyrrolidone
  • Comparative Example 1 An organic thin film transistor was prepared and evaluated in the same manner as in Example 1 except that the organic semiconductor composition prepared in the same manner as in Example 3 was used and the volume of the droplets by the ink jet apparatus was changed to 2100 pl. As a result, the threshold voltage in the current saturation region was ⁇ 2.5 V, and the field effect mobility ⁇ was 0.072 cm 2 / Vs. The results are shown in Table 1.
  • FIG. 20 is a diagram showing the relationship between the gate voltage and the drain current of the organic thin film transistor fabricated in Comparative Example 1.
  • FIG. 21 is a polarization micrograph of the organic semiconductor layer of the organic thin film transistor fabricated in Comparative Example 1.
  • FIG. 22 is an example of a result obtained by measuring the thickness of the organic semiconductor layer in the arrow direction shown in FIG.
  • FIG. 23 shows the measurement results of the average surface roughness (Ra) of the smooth portion on the right side of the channel portion of the organic thin film transistor fabricated in Comparative Example 1.
  • Ra was 2.4 nm. The value is larger than that of the example, and it can be seen that a discontinuous crystal aggregate is formed instead of a flat crystal.
  • Example 6 (1) Fabrication of gate electrode Fabricated in the same manner as in Example 1.
  • Comparative Example 2 An organic semiconductor material represented by the formula (3), polystyrene having a weight average molecular weight of 2500 as a binder resin, mesitylene and 3,3,5-trimethylcyclohexanone in a mass ratio of 0.18: 0.12: 84.7: 15
  • the organic semiconductor composition was prepared by mixing and dissolving at a ratio of 0.0.
  • the organic semiconductor composition was applied to a substrate produced in the same manner as in Example 6 using a spin coater to produce an organic thin film transistor and evaluated. The evaluation results are shown in Table 2. As a result of microscopic observation, coarse crystal grains were present in the channel portion, which prevented the formation of tabular crystals. In Table 2, the thickness of the flat portion of the channel portion is shown in place of the thickness of the plate crystal.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)

Abstract

La présente invention vise à proposer un transistor à film mince organique présentant une mobilité améliorée. A cette fin, le transistor à film mince organique selon l'invention comprend une section canal (11a) ménagée entre une électrode de source (11) et une électrode de drain (13), ladite section canal étant configurée à partir d'une couche semi-conductrice organique (13) contenant un matériau semi-conducteur organique. La section canal contient un cristal semi-conducteur organique planaire présentant une rugosité de surface moyenne (Ra) de 2 nm ou moins pour 5 m carrés, et l'épaisseur de film du cristal semi-conducteur organique planaire est de 40 nm ou moins.
PCT/JP2014/001176 2013-03-04 2014-03-04 Transistor à film mince organique et procédé de fabrication dudit transistor WO2014136436A1 (fr)

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JPWO2015076171A1 (ja) * 2013-11-21 2017-03-16 株式会社ダイセル 有機トランジスタ製造用溶剤
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