WO2012090462A1 - 有機半導体材料、当該材料を含んでなる塗布液、及び有機薄膜トランジスタ - Google Patents
有機半導体材料、当該材料を含んでなる塗布液、及び有機薄膜トランジスタ Download PDFInfo
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- WO2012090462A1 WO2012090462A1 PCT/JP2011/007241 JP2011007241W WO2012090462A1 WO 2012090462 A1 WO2012090462 A1 WO 2012090462A1 JP 2011007241 W JP2011007241 W JP 2011007241W WO 2012090462 A1 WO2012090462 A1 WO 2012090462A1
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- Prior art keywords
- organic
- film transistor
- thin film
- organic semiconductor
- organic thin
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Images
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- H10K85/731—Liquid crystalline materials
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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]
- H10K10/464—Lateral top-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
- 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
- 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
Definitions
- the present invention relates to an organic semiconductor material, a coating liquid containing the material, and an organic thin film transistor manufactured using the coating liquid. Moreover, this invention relates to the apparatus provided with the said organic thin-film transistor.
- a thin film transistor (TFT: Thin Film Transistor) is widely used as a switching element for display of a liquid crystal display device or the like.
- a typical TFT is formed by laminating 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 at a predetermined interval on the semiconductor layer. .
- the organic 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.
- a CVD apparatus used for manufacturing such a TFT using silicon is very expensive, and a display device using the TFT.
- Such an increase in size has a problem in that it involves a significant increase in manufacturing costs.
- 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 thus there is a problem that a lightweight resin substrate cannot be used. there were.
- a TFT using an organic substance instead of amorphous or polycrystalline silicon (hereinafter sometimes abbreviated as an organic TFT) has been proposed.
- a film forming method used for forming a TFT with an organic material a vacuum deposition method, a coating method, or the like is known.
- an increase in the size of a device (TFT High density and large size integrated circuit) can be realized.
- the process temperature required for film formation can be made relatively low, there is an advantage that there are few restrictions when selecting the material to be used for the substrate, and its practical application is expected.
- the use of a coating method as a film forming method is expected to improve the use efficiency of the material and significantly reduce the cost. Therefore, an organic semiconductor material suitable for the coating method is more demanded.
- a practical organic TFT requires high carrier mobility and excellent storage stability.
- the organic semiconductor material to be used needs to be soluble in a solvent, unlike the case of using a film forming method by a vacuum evaporation method.
- an organic semiconductor material having high mobility (hereinafter, carrier mobility may be simply referred to as mobility) is an organic compound in which a ⁇ -conjugated system is spread, and is often difficult to dissolve in a solvent.
- the solubility in a solvent is improved by heating, the coating liquid of the organic semiconductor material may be manufactured by heating.
- parameters to be controlled such as consideration of the amount of evaporation of the solvent in the manufacturing process of the coating liquid, temperature control in the film forming process, and the like may increase power consumption. Therefore, there has been a demand for an organic semiconductor material having higher solubility while having high carrier mobility and excellent storage stability.
- Non-Patent Document 1 discloses 2,7-dioctylnaphtho [1,2- as an organic semiconductor material having solubility and oxidation stability as a tetracyclic condensed ring compound in which two thiophene skeletons are condensed on a naphthalene ring.
- b: 5,6-b ′] dithiophene is disclosed.
- Patent Document 1 discloses an organic transistor using a six-ring condensed ring compound in which two benzothiophene skeletons are condensed on a naphthalene ring as an organic semiconductor layer, and has a high charge mobility and a large current on / off ratio. And it is disclosed that it is excellent in storage stability. Moreover, the organic transistor which formed the organic-semiconductor layer using the said compound using the wet process is disclosed. However, this organic semiconductor material is not sufficiently soluble, and no improvement in the mobility of the organic TFT was observed.
- An organic semiconductor material represented by the following formula (1) (Wherein R 1 , R 3 , R 4 and R 6 are each independently a hydrogen atom, a linear alkyl group having 3 to 20 carbon atoms, or a branched alkyl group having 3 to 40 carbon atoms. R 2 and R 5 are each independently a hydrogen atom, a linear alkyl group having 3 to 11 carbon atoms, or a branched alkyl group having 3 to 40 carbon atoms. However, two or more of R 1 to R 6 are alkyl groups. ) 2. 2. The organic semiconductor material according to 1, wherein R 1 , R 3 , R 4 and R 6 are hydrogen atoms. 3. 2.
- a coating solution comprising the organic semiconductor material according to any one of 1 to 6 and an organic solvent.
- the organic thin-film transistor provided with the organic-semiconductor layer manufactured using the coating liquid as described in 9.7. 10. 10.
- 11. The organic thin film transistor according to 10, wherein one of the source electrode and the drain electrode is made of a material having a work function of 4.2 eV or more and the other is made of a material having a work function of 4.3 eV or less.
- 12 12.
- An apparatus comprising the organic thin film transistor according to any one of 13.8 to 12.
- an organic semiconductor material having high carrier mobility, storage stability in the air, and high solubility in a solvent can be provided.
- the organic semiconductor material of the present invention is a compound represented by the following formula (1).
- R 1 , R 3 , R 4 and R 6 are each independently a hydrogen atom, a linear alkyl group having 3 to 20 carbon atoms, or a branched alkyl group having 3 to 40 carbon atoms.
- R 2 and R 5 are each independently a hydrogen atom, a linear alkyl group having 3 to 11 carbon atoms, or a branched alkyl group having 3 to 40 carbon atoms.
- two or more of R 1 to R 6 are alkyl groups.
- the “organic semiconductor” is a material that functions as a semiconductor layer of an organic TFT and exhibits TFT characteristics.
- the field-effect mobility obtained by the following formula (A) is 1 ⁇ 10 ⁇ 3 cm 2 / Vs or more, or 1 ⁇ 10 ⁇ 2 cm 2 / Vs or more.
- the organic semiconductor material of the present invention has a basic structure of a six-ring condensed ring structure in which two thiophene rings are condensed on a naphthalene ring and benzene rings are condensed on both sides of the thiophene ring.
- a condensed ring structure there are a plurality of structural isomers.
- the naphtho [1,2-b: 5: , 6-b ′] benzo [b] dithiophene skeleton is preferred.
- this skeleton alone is insoluble in organic solvents.
- a positive influence on mobility due to the alkyl substituents of R 1 to R 6 cannot be expected.
- the alkyl substituents of R 1 to R 6 contribute to the intermolecular interaction due to van der Waals force, thereby preventing the decrease in crystallinity and favorably affecting mobility. It is considered that the degree of freedom of conformational change of R 1 to R 6 affects the solubility. For this reason, the organic semiconductor material of the present invention has a crystalline property that affects mobility, particularly when two or more of R 1 to R 6 are linear alkyl groups or branched alkyl groups having a specific number of carbon atoms. The decrease can be suppressed and high solubility in a solvent can be obtained.
- R 1 to R 6 are preferably such that R 1 , R 3 , R 4 and R 6 are hydrogen atoms; R 1 , R 2 , R 4 and R 5 are hydrogen atoms; or R 2 , R 3 , R 5 and R 6 are hydrogen atoms. That is, the compound represented by the formula (1) is preferably any one of the compounds represented by the following formula. Among the above compounds, the following compounds are more preferable because high mobility and high solubility can be obtained. As a reason for the high mobility expression, it is conceivable to suppress the decrease in crystallinity.
- R 1 to R 6 are more preferably R 1 , R 3 , R 4 and R 6 are hydrogen atoms, and R 2 and R 5 are each a straight chain having 3 to 11 carbon atoms.
- R 2 and R 5 are linear alkyl groups having 4 to 6 carbon atoms because the solubility is obtained while the crystallinity is high, and thus the mobility is high. In addition, improvement in heat resistance can be expected.
- R 2 and R 5 are more preferably straight chain alkyl groups having 8 to 11 carbon atoms, since high solubility is obtained, which is suitable for the coating process.
- R 2 and R 5 may be the same or different, and can be a linear alkyl group having 5 to 11 carbon atoms.
- R 1 to R 6 are more preferably R 1 , R 2 , R 4 and R 5 are hydrogen atoms, and R 3 and R 6 are each a straight chain having 3 to 20 carbon atoms.
- R 3 and R 6 may be the same or different, and can be a linear alkyl group having 5 to 12 carbon atoms.
- R 1 to R 6 are more preferably R 2 , R 3 , R 5 and R 6 are hydrogen atoms, and R 1 and R 4 are each a group having 3 to 20 carbon atoms.
- R 1 and R 4 may be the same or different and may be a linear alkyl group having 4 to 12, 6 to 10 or 8 carbon atoms.
- Another organic semiconductor material of the present invention is a compound represented by the following formula (5).
- R 13 , R 14 , R 15 and R 16 are each independently a linear alkyl group having 3 to 11 carbon atoms or a branched alkyl group having 3 to 40 carbon atoms.
- Examples of the linear alkyl group of R 1 to R 6 and R 13 to R 16 include n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n -Nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n -Nonadecyl group, n-icosane group and the like.
- Examples of the branched alkyl group of R 1 to R 6 and R 13 to R 16 include isopropyl group, s-butyl group, isobutyl group, t-butyl group, 2-ethylbutyl group, 2-propylpentyl group, and 3-ethylpentyl group.
- 4-propylheptyl group, 5-ethylheptyl group, 5-propyloctyl group, 6-methylheptyl group, 6-ethyloctyl group, 6-propylnonyl group, 7-methyloctyl group, 7-ethylnonyl group, 6- A propyl decyl group etc. are mentioned.
- organic semiconductor material of the present invention is not limited to the following specific examples.
- the organic semiconductor material of the present invention comprises a Kumada / Tamao / Colleu coupling reaction as shown in the following reaction (A), a boronic acid synthesis reaction as shown in (B), a bromination reaction as shown in (C), It can be synthesized by Suzuki-Miyaura coupling reaction as in D) and cyclization reaction as in (E).
- an electronic device such as a transistor
- a device with high field-effect mobility and a high on / off ratio can be obtained by using a material with high purity. Therefore, it is desirable to add purification by techniques such as column chromatography, recrystallization, distillation, sublimation, etc. as necessary. Preferably, it is possible to improve the purity by repeatedly using these purification methods or combining a plurality of methods. Furthermore, it is desirable to repeat sublimation purification at least twice as a final step of purification. By using these methods, it is preferable to use a material having a purity of 90% or more measured by HPLC, more preferably 95% or more, and particularly preferably 99% or more. In addition, the on / off ratio can be increased and the performance inherent to the material can be extracted.
- the organic semiconductor material of the present invention can be used as a coating material or a deposition material.
- the coating liquid of the present invention comprises the organic semiconductor material of the present invention and an organic solvent.
- the coating liquid of the present invention can be prepared, for example, by mixing an organic semiconductor material and an organic solvent and heating the solvent to the minimum temperature necessary for dissolution.
- concentration of a coating liquid can be suitably set in the range which does not impair the objective of this invention, it can illustrate as follows.
- organic solvent examples include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexane, and N-methyl-2-pyrrolidone (NMP); ester solvents such as ethyl acetate, butyl acetate, and ⁇ -butyl lactone; diethyl Ether solvents such as ether, dioxane, tetrahydrofuran (THF), anisole; aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, tetralin, indane; 1,2,4-trichlorobenzene, o-dichlorobenzene, etc.
- ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexane, and N-methyl-2-pyrrolidone (NMP)
- Aromatic halogenated hydrocarbon solvents such as 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, chloroform and dichloromethane; sulfoxide solvents such as dimethyl sulfoxide (DMSO) Can Of these, two or more organic solvents may be mixed and used.
- halogenated hydrocarbon solvents such as 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, chloroform and dichloromethane
- sulfoxide solvents such as dimethyl sulfoxide (DMSO)
- the concentration of the organic semiconductor material in the coating solution is, for example, in the range of 0.1% by mass to 10% by mass, and preferably 0.4% by mass or more for the reason described later.
- the coating liquid of this invention may further contain well-known organic-semiconductor materials, such as a pentacene and a thiophene oligomer, in the range which does not impair the effect of this invention.
- the element configuration of the organic thin film transistor of the present invention is controlled by applying at least a gate electrode, a source electrode and a drain electrode, an insulator layer and an organic semiconductor layer, and applying a voltage to the gate electrode.
- an organic-semiconductor layer contains the organic-semiconductor material of this invention mentioned above, It is characterized by the above-mentioned.
- the structure of the transistor is not particularly limited, and components other than the components of the organic semiconductor layer may have a known element configuration. A specific example of the element configuration of the organic thin film transistor will be described with reference to the drawings.
- 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.
- 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 organic semiconductor layer 13 forms a channel region, and is turned on / off by controlling a current flowing between the source electrode 11 and the drain electrode 12 with a 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.
- the insulating layer 14 and the gate electrode 15 are provided in this order.
- the organic thin film transistor of the present invention has a field effect transistor (FET: Field Effect Transistor) structure.
- FET Field Effect Transistor
- 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.
- the distance between the source electrode and the drain electrode is determined by the application using the organic thin film transistor of the present invention, and is usually about 0.1 ⁇ m to 1 mm.
- the organic thin film transistor of the present invention can be applied to any of these elements as long as the current applied between the source electrode and the drain electrode is controlled by the voltage applied to the gate electrode so that effects such as on / off operation and amplification are realized.
- the configuration is not limited.
- the top-and-bottom contact type organic thin film transistor 5 (Fig. 5) proposed by Yoshida et al. Of the National Institute of Advanced Industrial Science and Technology in the 49th Applied Physics Related Conference Lecture Collection 27a-M-3 (March 2002)
- a vertical organic thin film transistor 6 proposed by Kudo et al. Of Chiba University in the IEEJ Transactions 118-A (1998), page 1440.
- the 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 includes the organic semiconductor material of the present invention. It is important for the organic semiconductor layer to be a continuous crystal film with connected conduction paths. In order to obtain the film continuity, the coating method, coating solvent, coating solvent concentration, etc. were selected appropriately. A film formed with the coating liquid of the present invention is preferred. For example, in the spin coating method, when the solvent is toluene, a continuous film is easily obtained when the concentration of the organic semiconductor material of the present invention is 0.4% by mass or more.
- the coating method used for the method of forming the organic semiconductor layer is not particularly limited, and a known method can be applied.
- a molecular beam deposition method MBE method
- a vacuum deposition method a vacuum deposition method
- a chemical deposition method or a material dissolved in a solvent.
- Dipping method spin coating method, casting method, bar coating method, roll coating method, ink jet method, etc., coating method and baking, electropolymerization, molecular beam deposition, self assembly from solution, and these
- the above-described means is used to form the organic semiconductor layer material as described above.
- the crystallinity of the organic semiconductor layer is improved, field effect mobility is improved.
- the annealing temperature is preferably 50 to 200 ° C., more preferably 70 to 200 ° C., and the time is preferably 10 minutes to 12 hours, more preferably 1 to 10 hours.
- the organic semiconductor layer one kind of the compound represented by the formula (1) or (5) may be used, or a plurality of them may be combined, or a plurality of known semiconductors such as pentacene and thiophene oligomer may be used. A mixed thin film or a laminated film may be used.
- 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 is often 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 for the gate electrode, the source electrode and the drain electrode is not particularly limited as long as it is a conductive material.
- 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. It is done.
- 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. If it is in this preferable range, the resistance is increased due to the thin film thickness, 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.
- another source electrode, drain electrode, gate electrode and a method for forming the source electrode are formed using a fluid electrode material such as a solution, paste, ink, or dispersion containing the above conductive material.
- a fluid electrode material such as a solution, paste, ink, or dispersion containing the above conductive material.
- a fluid electrode material containing a 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 metal fine 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 has been 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 (PEDOT) and polystyrene sulfonic acid is 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.
- the material for forming the source electrode and the drain electrode is preferably a material having a small electric resistance at the contact surface with the organic semiconductor layer among the examples described above.
- the electrical resistance at this time corresponds to the field effect mobility when the current control device is manufactured, and the resistance needs to be as small as possible in order to obtain a large mobility.
- This is generally determined by the magnitude relationship between the work function of the electrode material and the energy level of the organic semiconductor layer.
- the work function (W) of the electrode material is a
- the ionization potential of the organic semiconductor layer is (Ip) b
- the electron affinity (Af) of the organic semiconductor layer is c
- the following relational expression is preferably satisfied.
- a, b, and c are all positive values based on the vacuum level.
- ba ⁇ 1.5 eV (formula (I)) is preferable, and ba ⁇ 1.0 eV is more preferable. If the above relationship can be maintained in relation to the organic semiconductor layer, a high-performance device can be obtained.
- the electrode material has a work function as large as possible, and the work function is 4.0 eV or more.
- the work function is preferably 4.2 eV or more.
- the value of the work function of a metal is, for example, an effective metal having a work function of 4.0 eV or higher as described in Chemistry Handbook Fundamentals II-493 (revised 3 edition, published by The Chemical Society of Japan, Maruzen 1983)
- the high work function metal is mainly Ag (4.26, 4.52, 4.64, 4.74 eV), Al (4.06, 4.24, 4.41 eV), Au (5.1, 5.37, 5.47 eV), Be (4.98 eV), Bi (4.34 eV), Cd (4.08 eV), Co (5.0 eV), Cu (4.65 eV), Fe (4.5, 4.67, 4.81 eV), Ga (4.3 eV), Hg (4.4 eV), Ir (5.42, 5.76 eV), Mn (4.1 eV), Mo (4 .53, 4.55, 4.95 eV), Nb (4.02, 4.3) , 4.87 eV), Ni (5.04, 5.22, 5.35 eV), Os (5.93
- the work function of the electrode material is preferably as small as possible, and the work function is preferably 4.3 eV or less. More preferably, the work function is 3.7 eV or less.
- the low work function metal it has a work function of 4.3 eV or less as described in, for example, Chemical Handbook, Basics, pages II-493 (revised 3rd edition, published by The Chemical Society of Japan, Maruzen Co., Ltd.
- the electrode material contains one or more of these low work function substances, there is no particular limitation as long as the work function satisfies the above formula (II).
- the low work function metal easily deteriorates when exposed to moisture and oxygen in the atmosphere, it is desirable to coat with a stable metal in the air such as Ag or Au as necessary.
- the film thickness necessary for the coating is 10 nm or more, and as the film thickness increases, the film can be protected from oxygen and water. However, for practical reasons, the thickness is preferably 1 ⁇ m or less for the purpose of increasing productivity.
- 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 for n-type organic thin film transistors, LiF, Li 2 O, CsF, Na 2 CO 3 , KCl, MgF 2 , CaCO 3 and other alkali metal and alkaline earth metal ion bonds used for the cathode of organic EL A compound having Moreover, you may insert the compound used as an electron injection layer and an electron carrying layer by organic EL, such as Alq.
- 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 has the effect of lowering the threshold voltage by lowering the carrier injection barrier and driving the transistor at a low voltage. This is because there is a carrier trap at the interface between the organic semiconductor and the insulator layer.
- the first injected carrier is used to fill the trap, but by inserting a buffer layer, the trap is filled at a low voltage and the mobility is improved.
- 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, lanthanum oxide, fluorine oxide, magnesium oxide, bismuth oxide, bismuth titanate, niobium oxide, strontium bismuth titanate, strontium bismuth tantalate, tantalum pentoxide, bismuth tantalate niobate, trioxide Examples thereof include 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, A novolac resin, cyanoethyl pullulan, or the like can also be used.
- wax polyethylene, polychloropyrene, polyethylene terephthalate, polyoxymethylene, polyvinyl chloride, polyvinylidene fluoride, polysulfone, polyimide cyanoethyl pullulan, poly (vinylphenol) (PVP), poly (methyl methacrylate) (PMMA), polycarbonate (PC ), Polystyrene (PS), polyolefin, polyacrylamide, poly (acrylic acid), novolac resin, resole resin, polyimide, polyxylylene, epoxy resin, and also high molecular materials with high dielectric constant such as pullulan can be used. It is.
- a material having water repellency is particularly preferable.
- the interaction between the insulator layer and the organic semiconductor layer can be suppressed, and the crystallinity of the organic semiconductor layer can be improved by utilizing the cohesiveness inherent in the organic semiconductor, thereby improving the device performance.
- Examples of this include Yasuda et al. Jpn. J. et al. Appl. Phys. Vol. 42 (2003) p. 6614-6618 and Janos Veres et al. Chem. Mater. , Vol. 16 (2004) p. 4543-4555 can be mentioned.
- the organic semiconductor layer can be formed with less damage. Therefore, it is an effective method.
- 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 thickness 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. According to a desired element configuration, the substrate is charged, the gate electrode is formed, the insulator layer is formed, the organic semiconductor layer is formed, and the source electrode is formed. It is preferable to form a series of device manufacturing steps up to the formation of the drain electrode without being exposed to the atmosphere at all, because the device performance can be prevented from being impaired by moisture, oxygen, etc. in the atmosphere due to contact with the atmosphere.
- the process after film formation of the organic semiconductor layer is not exposed to the atmosphere at all, and the surface on which the organic semiconductor layer is laminated is irradiated with ultraviolet rays immediately before the film formation of the organic semiconductor layer. It is preferable to stack the organic semiconductor layer after cleaning and activation with ultraviolet / ozone irradiation, oxygen plasma, argon plasma or the like.
- 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.
- 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.
- the inorganic substance which has the insulation illustrated in the said insulator layer can also be used.
- an organic thin film light emitting transistor that emits light using a current flowing between a source electrode and a drain electrode and controls light emission by applying a voltage to the gate electrode. That is, an organic thin film transistor can be used as a light emitting element (organic EL). Since the transistor for controlling light emission and the light emitting element can be integrated, the aperture ratio of the display can be improved and the cost can be reduced by the simplification of the manufacturing process, which provides a great practical advantage. When used as an organic light emitting transistor, it is necessary to inject holes from one of the source electrode and the drain electrode and electrons from the other, and the following conditions are preferably satisfied in order to improve the light emitting performance.
- At least one of the source electrode and the drain electrode is a hole injecting electrode in order to improve the hole injecting property.
- a hole injection electrode is an electrode containing a substance having a work function of 4.2 eV or higher.
- at least one of the source electrode and the drain electrode is preferably an electron injectable electrode.
- An electron injecting electrode is an electrode containing a substance having a work function of 4.3 eV or less. More preferably, it is an organic thin-film light-emitting transistor provided with an electrode in which one is hole-injecting and the other is electron-injecting.
- the hole injection layer In order to improve the hole injection property, it is preferable to insert a hole injection layer between at least one of the source electrode and the drain electrode and the organic semiconductor layer.
- the hole injection layer include amine-based materials used as a hole injection material and a hole transport material in an organic EL device.
- an electron injecting layer between at least one of the source electrode and the drain electrode and the organic semiconductor layer.
- the electron injection material used for the organic EL element can be used for the electron injection layer as well as the hole. More preferably, one of the electrodes is provided with a hole injection layer and the other electrode is provided with an electron injection layer. It is a thin film light emitting transistor.
- the device using the organic thin film transistor of the present invention may be a device using the organic thin film transistor of the present invention, and examples thereof include a circuit, a personal computer, a display, and a mobile phone.
- the reactor was charged with 15.0 g (86 mmol) of 1-bromo-3-fluorobenzene and purged with nitrogen. 15 ml of dehydrated THF and Pd (dppf) Cl 2 .CH 2 Cl 2 (dichloro (diphenylphosphinoferrocene) palladium-methylene chloride complex) ) 0.70 g (0.86 mmol) was added. Next, 130 ml (0.13 mol) of 1M-n-pentylmagnesium bromide was added and stirred at room temperature for 10 minutes, and then heated and stirred at 60 ° C. for 11 hours.
- a reaction vessel was charged with 20.0 g (90.7 mmol) of 1,5-bis-methylsulfanyl-naphthalene and 400 ml of CH 2 Cl 2 and heated and stirred at 40 ° C. 31.9 g (199 mmol) of bromine was added dropwise, and the mixture was heated and stirred at 40 ° C. for 8 hours. The mixture was allowed to stand at room temperature for 12 hours, and the precipitated yellow needle crystals were filtered to obtain a crude product of compound (c). Recrystallization from ethyl acetate gave 22.1 g (yield 64%) of compound (c).
- Example 2 Compound (A-5) was synthesized in the same manner as in Example 1 except that n-heptylmagnesium bromide was used instead of n-pentylmagnesium bromide.
- Example 3 Compound (A-6) was synthesized in the same manner as in Example 1 except that n-octylmagnesium bromide was used instead of n-pentylmagnesium bromide.
- Example 4 Compound (A-9) was synthesized in the same manner as in Example 1 except that n-undecylmagnesium bromide was used instead of n-pentylmagnesium bromide.
- Example 5 Compound (B-3) was synthesized in the same manner as in Example 1 except that 1-bromo-4-fluorobenzene was used instead of 1-bromo-3-fluorobenzene.
- the structure of the compound (B-3) was confirmed by measurement by FD-MS (field desorption mass analysis). The measurement results of FD-MS are shown below.
- Example 6 Compound (B-5) was synthesized in the same manner as in Example 5 except that n-heptylmagnesium bromide was used instead of n-pentylmagnesium bromide.
- Example 7 Compound (B-6) was synthesized in the same manner as in Example 5 except that n-octylmagnesium bromide was used instead of n-pentylmagnesium bromide.
- Example 8 Compound (B-7) was synthesized in the same manner as in Example 5 except that n-nonylmagnesium bromide was used instead of n-pentylmagnesium bromide.
- Example 9 Compound (B-10) was synthesized in the same manner as in Example 5 except that n-dodecylmagnesium bromide was used instead of n-pentylmagnesium bromide.
- the structure of the compound (B-10) was confirmed by measurement by FD-MS (field desorption mass analysis). The measurement results of FD-MS are shown below.
- Example 10 Compound (C-7) was synthesized in the same manner as in Example 3, except that 1-bromo-2-fluorobenzene was used instead of 1-bromo-3-fluorobenzene.
- Example 11 Example 1 except that 1,2-dichloro-4-fluorobenzene was used in place of 1-bromo-3-fluorobenzene and n-butylmagnesium chloride was used in place of n-pentylmagnesium bromide.
- Comparative Example 1 Comparative compound (1) was synthesized in the same manner as in Example 1, except that n-dodecylmagnesium bromide was used instead of n-pentylmagnesium bromide.
- Comparative Compound (1) is a solution (coating solution) obtained at a high temperature of 90 ° C.
- parameters to be controlled such as solvent evaporation in the coating liquid manufacturing process and temperature control in the film forming process, are increased, and power consumption is also increased.
- Example 12 An organic thin film transistor was produced by the following procedure. The glass substrate was ultrasonically cleaned with a neutral detergent, pure water, acetone and ethanol for 30 minutes each, and then gold (Au) was formed to a thickness of 40 nm by a sputtering method to produce a gate electrode. Next, this substrate was set in a film forming section of a thermal CVD apparatus. In the raw material evaporation section, 250 mg of polyparaxylene derivative [polyparaxylene chloride (Parylene)] (trade name; diX-C, manufactured by Daisan Kasei Co., Ltd.) as a raw material for the insulator layer was placed in a petri dish.
- Parylene polyparaxylene derivative
- diX-C manufactured by Daisan Kasei Co., Ltd.
- the thermal CVD apparatus was evacuated with a vacuum pump and depressurized to 5 Pa, and then the evaporation part was heated to 180 ° C. and the polymerization part was heated to 680 ° C. and left for 2 hours to form an insulating layer having a thickness of 1 ⁇ m on the gate electrode. .
- toluene is added to the compound (A-3) to a concentration of 0.4% by mass, and the toluene is heated to 80 ° C. to dissolve the compound (A-3) to prepare a coating solution. did.
- An organic semiconductor layer having a thickness of 50 nm is formed by applying a coating solution prepared by a spin coater (Mikasa Co., Ltd .: 1H-D7) onto the substrate on which the insulator layer has been formed, and drying it at 80 ° C. in a nitrogen atmosphere. As a film formation. Next, gold (Au) was deposited to a thickness of 50 nm through a metal mask using a vacuum deposition apparatus, so that source and drain electrodes that were not in contact with each other were formed so that the distance (channel length L) was 250 ⁇ m. At that time, an organic thin film transistor was manufactured by forming a film so that the width (channel width W) of the source electrode and the drain electrode was 5 mm (see FIG. 3).
- the source - a current was passed by applying a voltage between the drain.
- the field effect mobility ⁇ of the holes was calculated from the following formula (A) and found to be 1.1 ⁇ 10 ⁇ 1 cm 2 / Vs.
- I D (W / 2L) ⁇ C ⁇ ⁇ ⁇ (V G ⁇ V T ) 2 (A)
- 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
- ⁇ is the field effect mobility
- VT is the gate threshold voltage
- V G is a gate voltage.
- Example 13 On the insulator layer produced in the same manner as in Example 12, 0.4% by mass of the compound (B-3) was dissolved in 70 ° C. toluene, and a film was formed with a spin coater (Mikasa Co., Ltd .: 1H-D7). The film was dried at 80 ° C. in a nitrogen atmosphere to form a 50 nm organic semiconductor layer. Thereafter, an electrode was produced in the same manner as in Example 12 to produce an organic thin film transistor. The obtained organic thin film transistor, in the same manner as in Example 12 was p-type driving at a gate voltage V G of -70V. The on / off ratio of the current between the source and drain electrodes was measured, and the hole field-effect mobility ⁇ was calculated. The results are shown in Table 2.
- Example 14 On the insulator layer produced in the same manner as in Example 12, 0.4% by mass of the compound (B-6) was dissolved in toluene at 50 ° C., and a film was formed with a spin coater (Mikasa Co., Ltd .: 1H-D7). The film was dried at 80 ° C. in a nitrogen atmosphere to form a 50 nm organic semiconductor layer. Thereafter, an electrode was produced in the same manner as in Example 12 to produce an organic thin film transistor. The obtained organic thin film transistor, in the same manner as in Example 12 was p-type driving at a gate voltage V G of -70V. The on / off ratio of the current between the source and drain electrodes was measured, and the hole field-effect mobility ⁇ was calculated. The results are shown in Table 2.
- Example 15 On the insulator layer produced in the same manner as in Example 12, 0.4% by mass of the compound (B-10) was dissolved in 70 ° C. toluene, and a film was formed with a spin coater (Mikasa Co., Ltd .: 1H-D7). The film was dried at 80 ° C. in a nitrogen atmosphere to form a 50 nm organic semiconductor layer. Thereafter, an electrode was produced in the same manner as in Example 12 to produce an organic thin film transistor. The obtained organic thin film transistor, in the same manner as in Example 12 was p-type driving at a gate voltage V G of -70V. The on / off ratio of the current between the source and drain electrodes was measured, and the hole field-effect mobility ⁇ was calculated. The results are shown in Table 2.
- Example 16 On the insulator layer produced in the same manner as in Example 12, 0.4% by mass of the compound (D-2) was dissolved in toluene at room temperature, and a film was formed with a spin coater (Mikasa Corp .: 1H-D7). The film was dried at 80 ° C. in an atmosphere to form a 50 nm organic semiconductor layer. Thereafter, an electrode was produced in the same manner as in Example 12 to produce an organic thin film transistor. The obtained organic thin film transistor, in the same manner as in Example 12 was p-type driving at a gate voltage V G of -70V. The on / off ratio of the current between the source and drain electrodes was measured, and the hole field-effect mobility ⁇ was calculated. The results are shown in Table 2.
- Comparative Example 2 An organic thin film transistor was fabricated in the same manner as in Example 12 except that the comparative compound (1) was used instead of the compound (A-3) as the material of the organic semiconductor layer and the coating liquid was prepared by heating to 90 ° C. .
- the obtained organic thin film transistor in the same manner as in Example 12, but was p-type driving at a gate voltage V G of -70V, the field effect mobility was very low. This is because in Comparative Example 2, the organic semiconductor layer was not uniformly formed because the film was formed at 90 ° C. close to the boiling point of toluene in order to maintain the solubility of the organic semiconductor material. It is conceivable that the mobility has greatly decreased due to reasons such as continuity.
- Example 17 An organic thin film transistor was produced by the following procedure. First, the surface of a Si substrate (also used as a P-type specific resistance 1 ⁇ cm gate electrode) was oxidized by a thermal oxidation method to produce a 300 nm thermal oxide film on the substrate to form an insulator layer. Further, after the SiO 2 film formed on one side of the substrate is completely removed by dry etching, chromium is deposited to a thickness of 20 nm by sputtering, and further gold (Au) is sputtered by 100 nm by sputtering. A film was formed and taken out as an electrode.
- a Si substrate also used as a P-type specific resistance 1 ⁇ cm gate electrode
- This substrate was ultrasonically cleaned with a neutral detergent, pure water, acetone and ethanol for 30 minutes each, and further subjected to ozone cleaning.
- the substrate is placed in a vacuum deposition apparatus (ULVAC, EX-400), and the compound (A-3) is deposited on the insulator layer at a deposition rate of 0.05 nm / s and a 50 nm thick organic semiconductor layer.
- a vacuum deposition apparatus UUV deposition apparatus
- gold was deposited to a thickness of 50 nm through a metal mask, so that a source electrode and a drain electrode that were not in contact with each other were formed so that a distance (channel length L) was 50 ⁇ m.
- an organic thin film transistor was manufactured by forming a film so that the width of the source electrode and the drain electrode (channel width W) was 1 mm.
- a gate voltage of 0 to ⁇ 100 V was applied to the gate electrode of the obtained organic thin film transistor, and a voltage of 0 to ⁇ 100 V was applied between the source and drain to pass a current.
- electrons are induced in the channel region (between source and drain) of the organic semiconductor layer, and operate as a p-type transistor.
- the field effect mobility ⁇ of holes in the current saturation region was 1.1 cm 2 / Vs.
- Example 18 On the insulator layer produced in the same manner as in Example 17, the compound (A-6) was formed. Thereafter, an electrode was produced in the same manner as in Example 17 to produce an organic thin film transistor. About the obtained organic thin-film transistor, it carried out similarly to Example 17, and computed the field effect mobility (micro
- Example 19 On the insulator layer produced in the same manner as in Example 17, the compound (A-9) was formed. Thereafter, an electrode was produced in the same manner as in Example 17 to produce an organic thin film transistor. About the obtained organic thin-film transistor, it carried out similarly to Example 17, and computed the field effect mobility (micro
- Example 20 On the insulator layer produced in the same manner as in Example 17, the compound (B-3) was formed. Thereafter, an electrode was produced in the same manner as in Example 17 to produce an organic thin film transistor. About the obtained organic thin-film transistor, it carried out similarly to Example 17, and computed the field effect mobility (micro
- Example 21 On the insulator layer produced in the same manner as in Example 17, the compound (B-5) was formed. Thereafter, an electrode was produced in the same manner as in Example 17 to produce an organic thin film transistor. About the obtained organic thin-film transistor, it carried out similarly to Example 17, and computed the field effect mobility (micro
- Example 22 On the insulator layer produced in the same manner as in Example 17, the compound (B-6) was formed. Thereafter, an electrode was produced in the same manner as in Example 17 to produce an organic thin film transistor. About the obtained organic thin-film transistor, it carried out similarly to Example 17, and computed the field effect mobility (micro
- Example 23 On the insulator layer produced in the same manner as in Example 17, the compound (B-10) was formed. Thereafter, an electrode was produced in the same manner as in Example 17 to produce an organic thin film transistor. About the obtained organic thin-film transistor, it carried out similarly to Example 17, and computed the field effect mobility (micro
- Comparative Example 3 An organic thin film transistor was produced in the same manner as in Example 17 except that the comparative compound (1) was used instead of the compound (A-3) as the material of the organic semiconductor layer. About the obtained organic thin-film transistor, it carried out similarly to Example 17, and computed the field effect mobility (micro
- Table 3 shows that the material of the present invention is excellent as an organic semiconductor material.
- Example 24 The carrier mobility after storing the organic thin film transistor produced in Example 17 in the atmosphere for 9 days was 1.1 cm 2 / Vs, and no deterioration was observed.
- Comparative Example 4 An organic thin film transistor was produced in the same manner as in Example 17 except that the following pentacene was used instead of the compound (A-3) as the material of the organic semiconductor layer. With respect to the obtained organic thin film transistor, the field effect mobility ⁇ of holes was calculated in the same manner as in Example 17. As a result, it showed 3.8 ⁇ 10 ⁇ 1 cm 2 / Vs, but it was stored in the atmosphere for 9 days. After that, the carrier mobility decreased to 1.3 ⁇ 10 ⁇ 3 cm 2 / Vs.
- the organic semiconductor material of the present invention can be used as a material for an organic semiconductor layer of an organic thin film transistor produced by a coating method. Since the organic semiconductor material of the present invention has high carrier mobility as a material of the organic semiconductor layer, the organic thin film transistor has a high response speed (driving speed) and high performance as a transistor.
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Abstract
Description
基本的には、加熱することにより溶媒への溶解度が向上するため、加熱により有機半導体材料の塗布液を製造できる場合がある。しかし、この場合、塗布液の製造工程における溶媒の蒸発量の配慮、成膜工程での温度制御等、制御すべきパラメーターが増加し、さらには、消費電力の増加も招くおそれがある。このため、高いキャリア移動度と優れた保存安定性を兼ね備えた上で、溶解性がより高い有機半導体材料が求められていた。
特にアセン系の縮合環化合物であるペンタセンは、その拡大したπ共役系によりアモルファスシリコン並みの高いキャリア移動度を示す材料として注目され、研究が盛んに行われている。しかしながら、ペンタセンは、溶媒への溶解性が低いために塗布法に適しておらず、また、大気中での保存安定性が低いという問題点があった。
また、ポリ-3-ヘキシルチオフェンに代表されるポリチオフェン類は、溶媒に可溶であり、溶解性という点では、塗布法に適した有機半導体材料であるが、大気中での保存安定性が低いという課題がある。
非特許文献1には、溶解性と酸化安定性を備えた有機半導体材料として、ナフタレン環にチオフェン骨格が2個縮合した4環の縮合環化合物として、2,7-ジオクチルナフト[1,2-b:5,6-b’]ジチオフェンが開示されている。この文献において前記の化合物は、溶解性を有するものの得られる塗布フィルムの物性が悪く、キャリア移動度が良くないと結論されている。
本発明の他の目的は、上記有機半導体材料を含んでなる塗布液、及び当該塗布液を用いて製造した有機薄膜トランジスタを提供することである。
1.下記式(1)で表される有機半導体材料。
R2及びR5は、それぞれ独立に、水素原子、炭素数3~11の直鎖アルキル基、又は炭素数3~40の分岐アルキル基である。
但し、R1~R6のうちの2以上がアルキル基である。)
2.R1、R3、R4及びR6が水素原子である1に記載の有機半導体材料。
3.R1、R2、R4及びR5が水素原子である1に記載の有機半導体材料。
4.R2、R3、R5及びR6が水素原子である1に記載の有機半導体材料。
5.下記に示される1に記載の有機半導体材料。
7.1~6のいずれかに記載の有機半導体材料と有機溶剤を含んでなる塗布液。
8.7に記載の塗布液を用いて製造した有機薄膜トランジスタ。
9.7に記載の塗布液を用いて製造した有機半導体層を備えた有機薄膜トランジスタ。
10.ソース電極及びドレイン電極を有し、ソース-ドレイン間を流れる電流を利用して発光し、ゲート電極に電圧を印加することによって発光を制御する8又は9に記載の有機薄膜トランジスタ。
11.前記ソース電極及びドレイン電極の一方が仕事関数4.2eV以上の物質からなり、他方が仕事関数4.3eV以下の物質からなる10に記載の有機薄膜トランジスタ。
12.前記ソース及びドレイン電極と有機半導体層の間にバッファ層を有する10又は11に記載の有機薄膜トランジスタ。
13.8~12のいずれかに記載の有機薄膜トランジスタを備えた装置。
R2及びR5は、それぞれ独立に、水素原子、炭素数3~11の直鎖アルキル基、又は炭素数3~40の分岐アルキル基である。
但し、R1~R6のうちの2以上がアルキル基である。)
本発明の有機半導体材料では、R1~R6のアルキル置換基がファン・デル・ワールス力による分子間の相互作用に寄与して結晶性の低下を防いで移動度に好影響を与え、且つR1~R6のコンホメーション変化の自由度が溶解性に影響を与えると考えられる。
このため、本発明の有機半導体材料は、特にR1~R6のうち2以上が、特定の炭素数の直鎖アルキル基又は分岐アルキル基であることにより、移動度に影響を与える結晶性の低下を抑制し、かつ溶媒に対する高い溶解性を得ることができる。
即ち、式(1)で表わされる化合物は、好ましくは下記式で表わされる化合物のいずれかである。
式(1)において、R1~R6は、より好ましくは、R1、R2、R4及びR5が水素原子であり、R3及びR6が、それぞれ炭素数3~20の直鎖アルキル基又は炭素数3~40の分岐アルキル基である。R3及びR6が炭素数4~12の直鎖アルキル基であると結晶性が高いまま溶解性が得られるため移動度が高く、また、塗布プロセスに好適であるためさらに好ましい。R3及びR6を、同一でも異なってもよくて、炭素数5~12の直鎖アルキル基とすることができる。
また、式(1)において、R1~R6は、より好ましくは、R2、R3、R5及びR6が水素原子であり、R1及びR4が、それぞれ炭素数3~20の直鎖アルキル基又は炭素数3~40の分岐アルキル基である。R1及びR4を、同一でも異なってもよくて、炭素数4~12,6~10又は8の直鎖アルキル基とすることができる。
R1~R6及びR13~R16の分岐アルキル基としては、イソプロピル基、s-ブチル基、イソブチル基、t-ブチル基、2-エチルブチル基、2-プロピルペンチル基、3-エチルペンチル基、4-プロピルヘプチル基、5-エチルヘプチル基、5-プロピルオクチル基、6-メチルヘプチル基、6-エチルオクチル基、6-プロピルノニル基、7-メチルオクチル基、7-エチルノニル基、6-プロピルデシル基等が挙げられる。
本発明の塗布液は、本発明の有機半導体材料と有機溶剤を含んでなる。
本発明の塗布液は、例えば有機半導体材料と有機溶媒を混合し、溶解に必要な最低限の温度まで溶媒を加熱することにより調製することができる。
有機溶媒の種類、及び塗布液の濃度は、本発明の目的が損なわれない範囲で適宜設定できるが、次のように例示することができる。
また、本発明の塗布液は、本発明の効果を損なわない範囲で、ペンタセン、チオフェンオリゴマー等の公知の有機半導体材料をさらに含んでもよい。
次に、本発明の有機薄膜トランジスタの素子構成について説明する。
本発明の有機薄膜トランジスタの素子構成は、少なくともゲート電極、ソース電極及びドレイン電極の3端子、絶縁体層並びに有機半導体層が設けられ、ソース-ドレイン間電流をゲート電極に電圧を印加することによって制御する薄膜トランジスタである。そして、有機半導体層が上述した本発明の有機半導体材料を含むことを特徴とする。
トランジスタの構造は、特に限定されず、有機半導体層の成分以外が公知の素子構成を有するものであってもよい。有機薄膜トランジスタの素子構成の具体例を図を用いて説明する。
図1の有機薄膜トランジスタ1は、基板10上に、相互に所定の間隔をあけて対向するように形成されたソース電極11及びドレイン電極12を有する。そして、ソース電極11、ドレイン電極12及びそれらの間の間隙を覆うように有機半導体層13が形成され、さらに、絶縁体層14が積層されている。絶縁体層14の上部であって、かつソース電極11及びドレイン電極12の間の間隙上にゲート電極15が形成されている。
例えば、産業技術総合研究所の吉田らにより第49回応用物理学関係連合講演会講演予稿集27a-M-3(2002年3月)において提案されたトップアンドボトムコンタクト型有機薄膜トランジスタ5(図5参照)や、千葉大学の工藤らにより電気学会論文誌118-A(1998)1440頁において提案された縦形の有機薄膜トランジスタ6(図6参照)のような素子構成を有するものであってもよい。
以下、有機薄膜トランジスタの構成部材について説明する。
本発明の有機薄膜トランジスタにおける有機半導体層は、本発明の有機半導体材料を含む。有機半導体層は、伝導パスがつながった連続性のある結晶膜であることが重要であり、膜の連続性を得るためには、塗布法、塗布溶媒、塗布溶媒の濃度等を適切に選んだ本発明の塗布液で成膜した膜であると好ましい。例えば、スピンコーティング法においては、溶媒をトルエンとした場合、本発明の有機半導体材料が0.4質量%以上の濃度であると、連続性のある膜が得られやすい。
有機半導体層の結晶性を向上させると電界効果移動度が向上するため、成膜方法に関わらず成膜後にアニーリングを実施することも高性能デバイスが得られるため好ましい。アニーリングの温度は50~200℃が好ましく、70~200℃であるとさらに好ましく、時間は10分~12時間が好ましく、1~10時間であるとさらに好ましい。
本発明において、有機半導体層には、式(1)又は(5)で示される化合物の1種類を用いてもよく、複数を組み合わせたり、ペンタセンやチオフェンオリゴマー等の公知の半導体を用いて複数の混合薄膜又は積層して用いてもよい。
本発明の有機薄膜トランジスタにおける基板は、有機薄膜トランジスタの構造を支持する役目を担うものであり、材料としてはガラスの他、金属酸化物や窒化物等の無機化合物、プラスチックフィルム(PET,PES,PC)や金属基板又はこれら複合体や積層体等も用いることが可能である。また、基板以外の構成要素により有機薄膜トランジスタの構造を十分に支持し得る場合には、基板を使用しないことも可能である。また、基板の材料としてはシリコン(Si)ウエハが用いられることが多い。この場合、Si自体をゲート電極兼基板として用いることができる。また、Siの表面を酸化し、SiO2を形成して絶縁層として活用することも可能である。この場合、基板兼ゲート電極のSi基板にリード線接続用の電極として、Au等の金属層を成膜することもある。
本発明の有機薄膜トランジスタにおける、ゲート電極、ソース電極及びドレイン電極の材料としては、導電性材料であれば特に限定されず、白金、金、銀、ニッケル、クロム、銅、鉄、錫、アンチモン、鉛、タンタル、インジウム、パラジウム、テルル、レニウム、イリジウム、アルミニウム、ルテニウム、ゲルマニウム、モリブデン、タングステン、酸化スズ・アンチモン、酸化インジウム・スズ(ITO)、フッ素ドープ酸化亜鉛、亜鉛、炭素、グラファイト、グラッシーカーボン、銀ペースト及びカーボンペースト、リチウム、ベリリウム、ナトリウム、マグネシウム、カリウム、カルシウム、スカンジウム、チタン、マンガン、ジルコニウム、ガリウム、ニオブ、ナトリウム-カリウム合金、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム混合物、リチウム/アルミニウム混合物等が用いられる。
電極材料の仕事関数(W)をa、有機半導体層のイオン化ポテンシャルを(Ip)b、有機半導体層の電子親和力(Af)をcとすると、以下の関係式を満たすことが好ましい。ここで、a、b及びcはいずれも真空準位を基準とする正の値である。
これらの中でも、貴金属(Ag,Au,Cu,Pt),Ni,Co,Os,Fe,Ga,Ir,Mn,Mo,Pd,Re,Ru,V,Wが好ましい。金属以外では、ITO、ポリアニリンやPEDOT:PSSのような導電性ポリマー及び炭素が好ましい。電極材料としてはこれらの高仕事関数の物質を1種又は複数含んでいても、仕事関数が前記式(I)を満たせば特に制限を受けるものではない。
低仕事関数金属の具体例としては、例えば化学便覧 基礎編II-493頁(改訂3版 日本化学会編 丸善株式会社発行1983年)に記載されている4.3eV又はそれ以下の仕事関数をもつ有効金属の前記リストから選別すればよく、Ag(4.26eV),Al(4.06,4.28eV),Ba(2.52eV),Ca(2.9eV),Ce(2.9eV),Cs(1.95eV),Er(2.97eV),Eu(2.5eV),Gd(3.1eV),Hf(3.9eV),In(4.09eV),K(2.28eV),La(3.5eV),Li(2.93eV),Mg(3.66eV),Na(2.36eV),Nd(3.2eV),Rb(4.25eV),Sc(3.5eV),Sm(2.7eV),Ta(4.0,4.15eV),Y(3.1eV),Yb(2.6eV),Zn(3.63eV)等が挙げられる。これらの中でも、Ba,Ca,Cs,Er,Eu,Gd,Hf,K,La,Li,Mg,Na,Nd,Rb,Y,Yb,Znが好ましい。電極材料としてはこれらの低仕事関数の物質を1種又は複数含んでいても、仕事関数が前記式(II)を満たせば特に制限を受けるものではない。ただし、低仕事関数金属は、大気中の水分や酸素に触れると容易に劣化してしまうので、必要に応じてAgやAuのような空気中で安定な金属で被覆することが望ましい。被覆に必要な膜厚は10nm以上必要であり、膜厚が厚くなるほど酸素や水から保護することができるが、実用上、生産性を上げる等の理由から1μm以下にすることが望ましい。
本発明の有機薄膜トランジスタでは、例えば、注入効率を向上させる目的で、有機半導体層とソース電極及びドレイン電極との間に、バッファ層を設けてもよい。バッファ層としてはn型有機薄膜トランジスタに対しては有機ELの陰極に用いられるLiF、Li2O、CsF、Na2CO3、KCl、MgF2、CaCO3等のアルカリ金属、アルカリ土類金属イオン結合を持つ化合物が望ましい。また、Alq等有機ELで電子注入層、電子輸送層として用いられる化合物を挿入してもよい。
p型有機薄膜トランジスタに対してはFeCl3、TCNQ、F4-TCNQ、HAT等のシアノ化合物、CFxやGeO2、SiO2、MoO3、V2O5、VO2、V2O3、MnO、Mn3O4、ZrO2、WO3、TiO2、In2O3、ZnO、NiO、HfO2、Ta2O5、ReO3、PbO2等のアルカリ金属、アルカリ土類金属以外の金属酸化物、ZnS、ZnSe等の無機化合物が望ましい。これらの酸化物は多くの場合、酸素欠損を起こし、これが正孔注入に好適である。さらにはTPDやNPD等のアミン系化合物やCuPc等有機EL素子において正孔注入層、正孔輸送層として用いられる化合物でもよい。また、上記の化合物二種類以上からなるものが望ましい。
本発明の有機薄膜トランジスタにおける絶縁体層の材料としては、電気絶縁性を有し薄膜として形成できるものであるのなら特に限定されず、金属酸化物(珪素の酸化物を含む)、金属窒化物(珪素の窒化物を含む)、高分子、有機低分子等室温での電気抵抗率が10Ωcm以上の材料を用いることができ、特に、比誘電率の高い無機酸化物皮膜が好ましい。
無機酸化物としては、酸化ケイ素、酸化アルミニウム、酸化タンタル、酸化チタン、酸化スズ、酸化バナジウム、チタン酸バリウムストロンチウム、ジルコニウム酸チタン酸バリウム、ジルコニウム酸チタン酸鉛、チタン酸鉛ランタン、チタン酸ストロンチウム、チタン酸バリウム、ランタン酸化物、フッ素酸化物、マグネシウム酸化物、ビスマス酸化物、チタン酸ビスマス、ニオブ酸化物,チタン酸ストロンチウムビスマス、タンタル酸ストロンチウムビスマス、五酸化タンタル、タンタル酸ニオブ酸ビスマス、トリオキサイドイットリウム及びこれらを組合せたもの等が挙げられ、酸化ケイ素、酸化アルミニウム、酸化タンタル、酸化チタンが好ましい。
また、窒化ケイ素(Si3N4、SixNy(x、y>0))、窒化アルミニウム等の無機窒化物も好適に用いることができる。
前記アルコキシド金属における金属としては、例えば、遷移金属、ランタノイド、又は主族元素から選択され、具体的には、バリウム(Ba)、ストロンチウム(Sr)、チタン(Ti)、ビスマス(Bi)、タンタル(Ta)、ジルコン(Zr)、鉄(Fe)、ニッケル(Ni)、マンガン(Mn)、鉛(Pb)、ランタン(La)、リチウム(Li)、ナトリウム(Na)、カリウム(K)、ルビジウム(Rb)、セシウム(Cs)、フランシウム(Fr)、ベリリウム(Be)、マグネシウム(Mg)、カルシウム(Ca)、ニオブ(Nb)、タリウム(Tl)、水銀(Hg)、銅(Cu)、コバルト(Co)、ロジウム(Rh)、スカンジウム(Sc)及びイットリウム(Y)等が挙げられる。また、前記アルコキシド金属におけるアルコキシドとしては、例えば、メタノール、エタノール、プロパノール、イソプロパノール、ブタノール、イソブタノール等を含むアルコール類、メトキシエタノール、エトキシエタノール、プロポキシエタノール、ブトキシエタノール、ペントキシエタノール、ヘプトキシエタノール、メトキシプロパノール、エトキシプロパノール、プロポキシプロパノール、ブトキシプロパノール、ペントキシプロパノール、ヘプトキシプロパノールを含むアルコキシアルコール類等から誘導されるものが挙げられる。
有機化合物を用いた絶縁体層としては、ポリイミド、ポリアミド、ポリエステル、ポリアクリレート、光ラジカル重合系、光カチオン重合系の光硬化性樹脂、アクリロニトリル成分を含有する共重合体、ポリビニルフェノール、ポリビニルアルコール、ノボラック樹脂、及びシアノエチルプルラン等を用いることもできる。
絶縁体層に用いる有機化合物材料、高分子材料として、特に好ましいのは撥水性を有する材料である。撥水性を有することにより絶縁体層と有機半導体層との相互作用を抑え、有機半導体が本来保有している凝集性を利用して有機半導体層の結晶性を高めデバイス性能を向上させることができる。このような例としては、Yasudaら Jpn.J.Appl.Phys.Vol.42(2003)pp.6614-6618に記載のポリパラキシリレン誘導体やJanos Veresら Chem.Mater.,Vol.16(2004)pp.4543-4555に記載のものが挙げられる。
また、前記絶縁体層は、陽極酸化膜、又は該陽極酸化膜を構成として含んでもよい。陽極酸化膜は封孔処理されることが好ましい。陽極酸化膜は、陽極酸化が可能な金属を公知の方法により陽極酸化することにより形成される。陽極酸化処理可能な金属としては、アルミニウム又はタンタルを挙げることができ、陽極酸化処理の方法には特に制限はなく、公知の方法を用いることができる。陽極酸化処理を行なうことにより、酸化被膜が形成される。陽極酸化処理に用いられる電解液としては、多孔質酸化皮膜を形成することができるものならばいかなるものでも使用でき、一般には、硫酸、燐酸、蓚酸、クロム酸、ホウ酸、スルファミン酸、ベンゼンスルホン酸等あるいはこれらを2種類以上組み合わせた混酸又はそれらの塩が用いられる。陽極酸化の処理条件は使用する電解液により種々変化するので一概に特定し得ないが、一般的には、電解液の濃度が1~80質量%、電解液の温度5~70℃、電流密度0.5~60A/cm2、電圧1~100ボルト、電解時間10秒~5分の範囲が適当である。好ましい陽極酸化処理は、電解液として硫酸、リン酸又はホウ酸の水溶液を用い、直流電流で処理する方法であるが、交流電流を用いることもできる。これらの酸の濃度は5~45質量%であることが好ましく、電解液の温度20~50℃、電流密度0.5~20A/cm2で20~250秒間電解処理するのが好ましい。
絶縁体層の厚さとしては、層の厚さが薄いと有機半導体に印加される実効電圧が大きくなるので、デバイス自体の駆動電圧、閾値電圧を下げることができるが、逆にソース-ゲート間のリーク電流が大きくなるので、適切な膜厚を選ぶ必要があり、通常10nm~5μm、好ましくは50nm~2μm、さらに好ましくは100nm~1μmである。
さらに、例えば、大気中に含まれる酸素、水等の有機半導体層に対する影響を考慮し、有機トランジスタ素子の外周面の全面又は一部に、ガスバリア層を形成してもよい。ガスバリア層を形成する材料としては、この分野で常用されるものを使用でき、例えば、ポリビニルアルコール、エチレン-ビニルアルコール共重合体、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリクロロトリフロロエチレン等が挙げられる。さらに、前記絶縁体層で例示した、絶縁性を有する無機物も使用できる。
また、電子の注入性を向上させるため、ソース電極及びドレイン電極の少なくとも一方は電子注入性電極であることが好ましい。電子注入性電極とは上記仕事関数4.3eV以下の物質を含む電極である。
さらに好ましくは一方が正孔注入性であり、且つ、もう一方が電子注入性である電極を備える有機薄膜発光トランジスタである。
また、電子の注入性を向上させるため、ソース電極及びドレイン電極の少なくとも一方電極と有機半導体層の間に電子注入性層を挿入すること好ましい。正孔と同じく電子注入層には有機EL素子に用いられる電子注入材料を用いることができる
さらに好ましくは一方の電極に正孔注入層を備え、且つ、もう一方の電極に電子注入層を備える有機薄膜発光トランジスタである。
化合物(A-3)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C32H32S2=480,found,m/z=480(M+,100)
装置:HX110(日本電子社製)
条件:加速電圧 8kV
スキャンレンジ m/z=50~1500
n-ペンチルマグネシウムブロミドの代わりに、n-ヘプチルマグネシウムブロミドを用いた他は実施例1と同様にして化合物(A-5)を合成した。
化合物(A-5)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C36H40S2=536,found,m/z=536(M+,100)
n-ペンチルマグネシウムブロミドの代わりに、n-オクチルマグネシウムブロミドを用いた他は実施例1と同様にして化合物(A-6)を合成した。
化合物(A-6)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C38H44S2=564,found,m/z=564(M+,100)
n-ペンチルマグネシウムブロミドの代わりに、n-ウンデシルマグネシウムブロミドを用いた他は実施例1と同様にして化合物(A-9)を合成した。
化合物(A-9)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C44H52S2=644,found,m/z=644(M+,100)
1-ブロモ-3-フルオロベンゼンの代わりに1-ブロモ-4-フルオロベンゼンを用いた他は実施例1と同様にして化合物(B-3)を合成した。
化合物(B-3)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C32H32S2=480,found,m/z=480(M+,100)
n-ペンチルマグネシウムブロミドの代わりに、n-ヘプチルマグネシウムブロミドを用いた他は実施例5と同様にして化合物(B-5)を合成した。
化合物(B-5)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C36H40S2=536,found,m/z=536(M+,100)
n-ペンチルマグネシウムブロミドの代わりに、n-オクチルマグネシウムブロミドを用いた他は実施例5と同様に化合物(B-6)を合成した。
化合物(B-6)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C38H44S2=564,found,m/z=564(M+,100)
n-ペンチルマグネシウムブロミドの代わりに、n-ノニルマグネシウムブロミドを用いた他は、実施例5と同様にして化合物(B-7)を合成した。
化合物(B-7)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C40H48S2=592,found,m/z=592(M+,100)
n-ペンチルマグネシウムブロミドの代わりに、n-ドデシルマグネシウムブロミドを用いた他は、実施例5と同様にして化合物(B-10)を合成した。
化合物(B-10)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C46H60S2=676,found,m/z=676(M+,100)
1-ブロモ-3-フルオロベンゼンの代わりに、1-ブロモ-2-フルオロベンゼンを用いた他は、実施例3と同様にして化合物(C-7)を合成した。
化合物(C-7)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C38H44S2=564,found,m/z=564(M+,100)
1-ブロモ-3-フルオロベンゼンの代わりに1,2-ジクロロ-4-フルオロベンゼンを用い、n-ペンチルマグネシウムブロミドの代わりにn-ブチルマグネシウムクロリドを用た他は、実施例1と同様にして化合物(D-2)を合成した。
化合物(D-2)の構造は、FD-MS(フィールドディソープションマス分析)の測定により確認した。FD-MSの測定結果を以下に示す。
FD-MS,calcd for C38H44S2=564,found,m/z=564(M+,100)
n-ペンチルマグネシウムブロミドの代わりに、n-ドデシルマグネシウムブロミドを用いた他は、実施例1と同様にして比較化合物(1)を合成した。
FD-MS,calcd for C46H60S2=676,found,m/z=676(M+,100)
実施例1~11及び比較例1で得た化合物(A-3)、(A-5)、(A-6)、(A-9)、(B-3)、(B-5)、(B-6)、(B-7)、(B-10)、(C-7)、(D-2)及び比較化合物(1)の溶解性を、トルエンに0.4質量%濃度溶解するために必要なトルエンの温度をそれぞれ測定することにより評価した。結果を表1に示す。
また、公知の方法で調製した下記比較例化合物(2)についても上記と同様に溶解性の評価を実施したが、溶媒に十分に溶解しなかった。
実施例12
有機薄膜トランジスタを以下の手順で作製した。
ガラス基板を中性洗剤、純水、アセトン及びエタノールで各30分超音波洗浄した後、スパッタ法にて金(Au)を40nm成膜してゲート電極を作製した。次いで、この基板を熱CVD装置の成膜部にセットした。
原料の蒸発部には、絶縁体層の原料のポリパラキシレン誘導体[ポリパラ塩化キシレン(Parylene)](商品名;diX-C,第三化成社製)250mgをシャーレに入れて設置した。熱CVD装置を真空ポンプで真空に引き、5Paまで減圧した後、蒸発部を180℃、重合部を680℃まで加熱して2時間放置しゲート電極上に厚さ1μmの絶縁体層を形成した。
次に、化合物(A-3)に濃度が0.4質量%となるようにトルエンを加えて、当該トルエンを80℃に加熱して、化合物(A-3)を溶解させて塗布液を調製した。前記絶縁体層まで成膜した基板の上にスピンコーター(ミカサ社製:1H‐D7)で調製した塗布液を塗布して成膜し、窒素雰囲気下80℃にて乾燥させ50nmの有機半導体層として成膜した。次いで、真空蒸着装置で金属マスクを通して金(Au)を50nmの膜厚で成膜することにより、互いに接しないソース及びドレイン電極を、間隔(チャンネル長L)が250μmになるように形成した。そのときソース電極とドレイン電極の幅(チャンネル幅W)は5mmとなるように成膜して有機薄膜トランジスタを作製した(図3参照)。
ID=(W/2L)・C・μ・(VG-VT)2 (A)
式中、IDはソース-ドレイン間電流、Wはチャンネル幅、Lはチャンネル長、Cはゲート絶縁体層の単位面積あたりの電気容量、μは電界効果移動度、VTはゲート閾値電圧、VGはゲート電圧である。各電圧の印加及びソース-ドレイン電極間電流の測定は、半導体特性評価システム(ケースレーインスツルメンツ(株)製 4200SCS)を用いて行った。
実施例12と同様に作製した絶縁体層上に、化合物(B-3)を70℃のトルエンに0.4質量%溶解させ、スピンコーター(ミカサ社製:1H‐D7)で成膜し、窒素雰囲気下80℃にて乾燥させ50nmの有機半導体層として成膜した。その後、実施例12と同様にして電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例12と同様にして、-70Vのゲート電圧VGにてp型駆動させた。ソース-ドレイン電極間の電流のオン/オフ比を測定し、正孔の電界効果移動度μを算出した。結果を表2に示す。
実施例12と同様に作製した絶縁体層上に、化合物(B-6)を50℃のトルエンに0.4質量%溶解させ、スピンコーター(ミカサ社製:1H‐D7)で成膜し、窒素雰囲気下80℃にて乾燥させ50nmの有機半導体層として成膜した。その後、実施例12と同様に電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例12と同様にして、-70Vのゲート電圧VGにてp型駆動させた。ソース-ドレイン電極間の電流のオン/オフ比を測定し、正孔の電界効果移動度μを算出した。結果を表2に示す。
実施例12と同様に作製した絶縁体層上に、化合物(B-10)を70℃のトルエンに0.4質量%溶解させ、スピンコーター(ミカサ社製:1H‐D7)で成膜し、窒素雰囲気下80℃にて乾燥させ50nmの有機半導体層として成膜した。その後、実施例12と同様にして電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例12と同様にして、-70Vのゲート電圧VGにてp型駆動させた。ソース-ドレイン電極間の電流のオン/オフ比を測定し、正孔の電界効果移動度μを算出した。結果を表2に示す。
実施例12と同様に作製した絶縁体層上に、化合物(D-2)を室温のトルエンに0.4質量%溶解させ、スピンコーター(ミカサ社製:1H‐D7)で成膜し、窒素雰囲気下80℃にて乾燥させ50nmの有機半導体層として成膜した。その後、実施例12と同様にして電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例12と同様にして、-70Vのゲート電圧VGにてp型駆動させた。ソース-ドレイン電極間の電流のオン/オフ比を測定し、正孔の電界効果移動度μを算出した。結果を表2に示す。
有機半導体層の材料として、化合物(A-3)の代わりに比較化合物(1)を用い、90℃に加熱して塗布液を調製した以外は、実施例12と同様にして有機薄膜トランジスタを作製した。得られた有機薄膜トランジスタについて、実施例12と同様にして、-70Vのゲート電圧VGにてp型駆動させたが、電界効果移動度は非常に低いものであった。
これは、比較例2では、有機半導体材料の溶解性を維持するため、トルエンの沸点に近い90℃で成膜しているために、有機半導体層が均一に形成されず、結晶粒間に不連続性が生じる等の理由で、移動度が大きく低下したことが考えられる。
実施例17
有機薄膜トランジスタを以下の手順で作製した。まず、Si基板(P型比抵抗1Ωcmゲート電極兼用)を熱酸化法にて表面を酸化させ、基板上300nmの熱酸化膜を作製して絶縁体層とした。さらに基板の一方に成膜したSiO2膜をドライエッチングにて完全に除去した後、スパッタ法にてクロムを20nmの膜厚で成膜し、さらにその上に金(Au)を100nmスパッタにて成膜し取り出し電極とした。この基板を、中性洗剤,純水,アセトン及びエタノールで各30分超音波洗浄し、さらにオゾン洗浄を行った。
次に、上記基板を真空蒸着装置(ULVAC社製,EX-400)に設置し、絶縁体層上に化合物(A-3)を0.05nm/sの蒸着速度で50nm膜厚の有機半導体層として成膜した。次いで、金属マスクを通して金を50nmの膜厚で成膜することにより、互いに接しないソース電極及びドレイン電極を、間隔(チャンネル長L)が50μmになるように形成した。そのときソース電極とドレイン電極の幅(チャンネル幅W)は1mmとなるように成膜して有機薄膜トランジスタを作製した。
実施例17と同様に作製した絶縁体層上に、化合物(A-6)を成膜した。その後、実施例17と同様にして電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例17と同様にして、正孔の電界効果移動度μを算出した。結果を表3に示す。
実施例17と同様に作製した絶縁体層上に、化合物(A-9)を成膜した。その後、実施例17と同様にして電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例17と同様にして、正孔の電界効果移動度μを算出した。結果を表3に示す。
実施例17と同様に作製した絶縁体層上に、化合物(B-3)を成膜した。その後、実施例17と同様にして電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例17と同様にして、正孔の電界効果移動度μを算出した。結果を表3に示す。
実施例17と同様に作製した絶縁体層上に、化合物(B-5)を成膜した。その後、実施例17と同様にして電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例17と同様にして、正孔の電界効果移動度μを算出した。結果を表3に示す。
実施例17と同様に作製した絶縁体層上に、化合物(B-6)を成膜した。その後、実施例17と同様にして電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例17と同様にして、正孔の電界効果移動度μを算出した。結果を表3に示す。
実施例17と同様に作製した絶縁体層上に、化合物(B-10)を成膜した。その後、実施例17と同様にして電極を作製し有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例17と同様にして、正孔の電界効果移動度μを算出した。結果を表3に示す。
有機半導体層の材料として、化合物(A-3)の代わりに比較化合物(1)を用いた以外は、実施例17と同様にして有機薄膜トランジスタを作製した。
得られた有機薄膜トランジスタについて、実施例17と同様にして、正孔の電界効果移動度μを算出した。結果を表3に示す。
実施例24
実施例17において作製した有機薄膜トランジスタを9日間大気中に保管した後のキャリア移動度は1.1cm2/Vsで劣化は見られなかった。
この明細書に記載の文献の内容を全てここに援用する。
Claims (13)
- R1、R3、R4及びR6が水素原子である請求項1に記載の有機半導体材料。
- R1、R2、R4及びR5が水素原子である請求項1に記載の有機半導体材料。
- R2、R3、R5及びR6が水素原子である請求項1に記載の有機半導体材料。
- 請求項1~6のいずれかに記載の有機半導体材料と有機溶剤を含んでなる塗布液。
- 請求項7に記載の塗布液を用いて製造した有機薄膜トランジスタ。
- 請求項7に記載の塗布液を用いて製造した有機半導体層を備えた有機薄膜トランジスタ。
- ソース電極及びドレイン電極を有し、ソース-ドレイン間を流れる電流を利用して発光し、ゲート電極に電圧を印加することによって発光を制御する請求項8又は9に記載の有機薄膜トランジスタ。
- 前記ソース電極及びドレイン電極の一方が仕事関数4.2eV以上の物質からなり、他方が仕事関数4.3eV以下の物質からなる請求項10に記載の有機薄膜トランジスタ。
- 前記ソース及びドレイン電極と有機半導体層の間にバッファ層を有する請求項10又は11に記載の有機薄膜トランジスタ。
- 請求項8~12のいずれかに記載の有機薄膜トランジスタを備えた装置。
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US13/997,929 US20140061616A1 (en) | 2010-12-28 | 2011-12-23 | Organic semiconductor material, coating liquid containing the material, and organic thin film transistor |
JP2012550720A JPWO2012090462A1 (ja) | 2010-12-28 | 2011-12-23 | 有機半導体材料、当該材料を含んでなる塗布液、及び有機薄膜トランジスタ |
CN2011800633969A CN103299446A (zh) | 2010-12-28 | 2011-12-23 | 有机半导体材料、含有该材料而成的涂布液以及有机薄膜晶体管 |
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WO2014156773A1 (ja) * | 2013-03-29 | 2014-10-02 | 新日鉄住金化学株式会社 | 芳香族複素環化合物、その製造方法、有機半導体材料及び有機半導体デバイス |
WO2015105059A1 (ja) * | 2014-01-09 | 2015-07-16 | 富士フイルム株式会社 | 有機トランジスタ、化合物、非発光性有機半導体デバイス用有機半導体材料、有機トランジスタ用材料、非発光性有機半導体デバイス用塗布溶液および非発光性有機半導体デバイス用有機半導体膜 |
WO2016051977A1 (ja) * | 2014-09-29 | 2016-04-07 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及びこれを用いた有機電界発光素子 |
JP2016092179A (ja) * | 2014-11-04 | 2016-05-23 | 山本化成株式会社 | 有機トランジスタ |
US10040794B2 (en) | 2014-05-07 | 2018-08-07 | Samsung Electronics Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
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US8901547B2 (en) * | 2012-08-25 | 2014-12-02 | Polyera Corporation | Stacked structure organic light-emitting transistors |
US9564604B2 (en) * | 2012-10-18 | 2017-02-07 | Nippon Kayaku Kabushiki Kaisha | Fused polycyclic aromatic compounds, organic semiconductor material and thin film including the same, and method for producing an organic semiconductor device |
WO2014136898A1 (ja) * | 2013-03-07 | 2014-09-12 | Dic株式会社 | 有機薄膜、これを用いた有機半導体デバイスおよび有機トランジスタ |
KR101764043B1 (ko) * | 2013-03-22 | 2017-08-01 | 후지필름 가부시키가이샤 | 유기 박막 트랜지스터, 유기 반도체 박막 및 유기 반도체 재료 |
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CN109461660A (zh) * | 2018-11-14 | 2019-03-12 | 合肥鑫晟光电科技有限公司 | 一种金属氧化物薄膜及其制备方法、薄膜晶体管和阵列基板 |
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CN103299446A (zh) | 2013-09-11 |
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