WO2005122278A1 - 有機半導体薄膜、有機半導体デバイス、有機薄膜トランジスタ及び有機エレクトロルミネッセンス素子 - Google Patents
有機半導体薄膜、有機半導体デバイス、有機薄膜トランジスタ及び有機エレクトロルミネッセンス素子 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
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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 a potential-jump barrier or a surface barrier
- 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
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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 a potential-jump barrier or a surface barrier
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
Definitions
- Organic semiconductor thin film organic semiconductor device, organic thin film transistor, and organic electroluminescent device
- the present invention relates to an organic semiconductor thin film, an organic semiconductor device, an organic thin film transistor, and an organic electroluminescent device.
- a display medium is formed by using an element utilizing liquid crystal, an organic electroluminescent element (hereinafter, also referred to as an organic EL element), electrophoresis, or the like.
- an organic electroluminescent element hereinafter, also referred to as an organic EL element
- electrophoresis or the like.
- display media in order to ensure uniformity of screen luminance and screen rewriting speed, a technique using an active driving element (TFT element) as an image driving element has become mainstream.
- TFT element active driving element
- these TFT elements are formed on a glass substrate, and a liquid crystal, an organic EL element, and the like are sealed.
- TFT element semiconductors such as a-Si (amorphous silicon) and p-Si (polysilicon) can be mainly used for the TFT element, and these S ⁇ conductors (and metal films as necessary) can be used.
- the TFT device is manufactured by multi-layering and sequentially forming source, drain and gate electrodes on the substrate. The manufacture of such TFT devices typically requires sputtering and other vacuum-based manufacturing processes.
- each layer must be formed by repeating the manufacturing process of the vacuum system including the vacuum chamber many times, and the equipment cost and the running cost are extremely enormous. Had become something.
- a TFT device it is usually necessary to repeat processes such as vacuum deposition, doping, photolithography, and development many times to form each layer.
- An element is formed on a substrate through dozens of steps.
- semiconductor part that is the key to switching operation multiple types of semiconductor layers such as P-type and n-type are stacked.
- it is not easy to change the equipment such as a need for a large design change of a manufacturing apparatus such as a vacuum chamber in response to a need for a large display screen.
- organic semiconductor materials as organic compounds having a high charge transport property has been energetically advanced.
- the organic semiconductor material can be subjected to a solution treatment by appropriately improving its molecular structure, and the obtained organic semiconductor solution is converted into an ink by a printing method including an ink-jet method, or by an application method. Layers can be formed.
- TFT elements can be formed on a transparent resin substrate. If a TFT element can be formed on a transparent resin substrate and the display element can be driven by the TFT element, the display will be lighter and more flexible than the conventional one, and will not break when dropped. It can be made into a display that is hard to crack.
- a thiophene polymer represented by P3HT is soluble in an organic solvent and can be used for production by a low-temperature process as described above.
- an organic semiconductor layer is formed using a material having a molecular weight distribution such as a polymer, many amorphous portions with disordered arrangement are formed in the layer. In such an amorphous part, the overlapping of the ⁇ -conjugated planes of the thiophene ring is small and the carrier movement is rate-limiting, so satisfactory TFT performance has not been obtained.
- polyascene conjugates such as pentacene have high crystallinity due to strong intermolecular cohesion, thereby exhibiting high carrier mobility and excellent semiconductor device characteristics. It has been reported that Further, by using a vapor deposition film pentacene arranged with high regularity, have been reported to express high carrier mobility (e.g., Non-Patent Document 4 reference.) 0
- the organic semiconductor thin film in order to obtain an organic semiconductor thin film exhibiting excellent TFT performance, the organic semiconductor thin film must have a crystalline structure in which molecules are arranged with high and regularity. Is considered important. However, there is a problem that many of these polyasenyl conjugates cannot be produced by coating because they are insoluble or hardly soluble in organic solvents.
- Patent Document 1 JP-A-5-55568
- Patent Document 2 JP-A-8-264805
- Non-Patent Document 1 “Science”, Vol. 289, 599 pages (2000)
- Non-patent Document 2 “Naturer” (Nature), vol. 403, p. 521 (2000)
- Non-Patent Document 3 "Advanced Material", 2002, Issue 2, p. 99
- Non-Patent Document 4 Appl.Phys. Lett., 1998, 72, 1854
- Non-Patent Document 5 Proc. ICSM- 2004
- Non-Patent Document 6 “Chemical Material”, 1998, Issue 10, p. 633
- An object of the present invention is to solve the above-mentioned problems of the prior art, to form an organic semiconductor thin film by coating, and to obtain a high carrier mobility by using the obtained organic semiconductor thin film.
- An object of the present invention is to provide an organic semiconductor device, an organic thin film transistor, and an organic EL element including the device or the transistor.
- An organic semiconductor thin film characterized in that the half-width of the diffraction peak having the maximum intensity in the vector is 0.4 ° or less.
- the organic semiconductor compound is mixed with an organic solvent, and is manufactured through a step of forming a film using a solution or a dispersion liquid at room temperature, and the X-ray diffraction vector of the film
- Item 3 The organic semiconductor thin film according to Item 1 or 2, wherein the organic solvent contains a non-halogen solvent.
- Item 3 The organic semiconductor thin film according to any one of Items 1 to 3, wherein the organic semiconductor compound has a weight average molecular weight Mw of 10,000 or less.
- Item 6 The organic semiconductor thin film according to any one of Items 1 to 5, wherein the content of the organic semiconductor conjugate is 95% or more.
- organic semiconductor thin film according to any one of Items 1 to 6, wherein the organic semiconductor compound is a ⁇ -conjugated compound containing two or more aromatic rings.
- Item 8 The organic semiconductor thin film according to Item 7, wherein the organic semiconductor conjugate has, as a partial structure, two or more types of aromatic hydrocarbon rings or two or more types of aromatic heterocycles.
- Item 8 The organic semiconductor thin film according to Item 7, wherein the organic semiconductor conjugate has three or more types of aromatic hydrocarbon rings or three or more types of aromatic heterocycles as a partial structure.
- the organic semiconductor compound includes a thiophene oligomer having a thiophene ring having a substituent and a partial structure in which at least two or more unsubstituted thione ring repeating units are continuous.
- Item 12 The organic semiconductor thin film according to Item 11, wherein the thiophene oligomer contains 3 to 20 thiophene rings.
- Item 12 The organic semiconductor thin film according to Item 11, wherein the thiophene ring contained in the thiophene oligomer has a ring force of up to 10.
- Item 13 The organic semiconductor thin film according to any one of Items 11 to 13, wherein the thiophene oligomer has a partial structure represented by the following general formula (1).
- R represents a substituent
- Item 15 The organic semiconductor thin film according to any one of Items 11 to 14, wherein a terminal group of the thiophene oligomer does not have a chenyl group. [0034] (Term 16)
- Item 16 The organic semiconductor thin film according to any one of Items 11 to 15, wherein the structure of the thiophene oligomer does not have a head-to-head structure.
- Item 18 An organic semiconductor device comprising the organic semiconductor thin film according to any one of items 1 to 16.
- Item 18 An organic thin film transistor, wherein the organic semiconductor thin film according to any one of items 1 to 16 is used for an organic semiconductor layer.
- Item 18 An organic electroluminescent device comprising the organic semiconductor device according to Item 17 or the organic thin film transistor according to Item 18.
- the organic semiconductor thin film of the present invention has provided an organic TFT and a field-effect transistor having high carrier mobility, and a switching element having the organic TFT and the field-effect transistor.
- FIG. 1 is a diagram showing a configuration example of an organic TFT according to the present invention.
- FIG. 2 is an example of a schematic equivalent circuit diagram of the organic TFT of the present invention.
- FIG. 3 is an example of an X-ray diffraction spectrum of the organic semiconductor thin film of the present invention.
- FIG. 4 is an example of an X-ray diffraction spectrum of the organic semiconductor thin film of the present invention.
- FIG. 5 is an example of an X-ray diffraction spectrum of the organic semiconductor thin film of the present invention.
- FIG. 6 is an example of an X-ray diffraction spectrum of a comparative organic semiconductor thin film.
- FIG. 7 is a schematic view showing an example of an organic EL device having a sealing structure.
- FIG. 8 is a schematic view showing an example of a substrate having a TFT used for an organic EL element.
- organic semiconductor thin film of the present invention by using the structure defined in any one of claims 1 to 16, an organic semiconductor thin film useful for thin film transistor use can be obtained.
- organic TFT organic thin film transistor
- the present inventors have found that a material such as a single crystal in which molecules are regularly arranged and which has high crystallinity has an X-ray It is known that a diffraction peak having a very small half width is obtained in the diffraction spectrum. Therefore, the material that forms a film that exhibits a diffraction peak with a smaller half-value width is an organic semiconductor thin film that exhibits excellent TFT performance, using the half-width of the diffraction peak as an index of the regularity of the molecular arrangement in the film. was found to form.
- the thiophene oligomer like the thiophene oligomer according to the present invention, it has a solubility site (thione ring site having a substituent) and a ⁇ stack formation site (continuous site of unsubstituted thiophene ring).
- a solubility site thione ring site having a substituent
- a ⁇ stack formation site continuous site of unsubstituted thiophene ring.
- an oligomer whose molecular weight is adjusted to a specific range (this is synonymous with adjusting the number of repeating units to a specific range) is molecularly designed and the oligomer is used. It became possible to form a coating film having an ideal molecular arrangement as seen in known pentacene and the like, and as a result, TFT performance was greatly improved.
- the organic semiconductor thin film of the present invention is an organic semiconductor conjugate (for an organic semiconductor conjugate, , which will be described later) and an organic solvent shown below, and prepared at room temperature using a solution or dispersion to form a film.
- the solution or dispersion at room temperature means that the solution or dispersion is formed when the organic semiconductor conjugate and the organic solvent are mixed under the conditions of 10 ° C to 80 ° C.
- the term “dispersion liquid” refers to a state in which the organic semiconductor compound is dispersed in the form of particles, but also includes a state in which the organic semiconductor compound is partially dissolved in the dispersion liquid. Further, as one embodiment of the dispersion, for example, it dissolves under a temperature condition of 80 ° C. to form a solution, but when the temperature returns to room temperature (usually a temperature around 25 ° C.), particles of the organic semiconductor compound are dispersed. , Aggregates, precipitates and the like are dispersed in an organic solvent.
- the organic solvent according to the invention is not particularly limited, and may be a single solvent or a mixed solvent.
- a non-halogen solvent is used.
- the non-halogen solvent used in the present invention include aliphatic solvents such as hexane and octane, alicyclic solvents such as cyclohexane, aromatic solvents such as benzene, toluene and xylene, tetrahydrofuran, dioxane, and the like.
- Ether-based solvents such as ethylene glycolone retinole ethere, Aniso monole, benzinooletinoleateneole, ethylenolefeinoleateneole, diphenineoleateneole, methylinolate Ethyl acetate, Ethyl acetate, Solvents such as ethyl solvent, alcohols such as methanol, ethanol, isopropanol, etc., Ketones such as acetone, methyl ethyl ketone, cyclohexanone, 2-hexanone, 2-heptanone, 3-heptanone Solvents, other dimethylformamide, dimethyl sulfoxide, di Ethylformamide, 1,3-dioxolan and the like.
- the organic solvent used in combination is not particularly limited, but is preferably methanol, ethanol, isopropanol, acetone, methylethylketone, methylisobutylketone, pyrrolidone, N-methylpyrrolidone.
- an alkyl ester of oxyisobutyrate or the like may be used as the ester solvent.
- the oxyisobutyrate ester include methyl ⁇ -methoxyisobutyrate, ethyl a-methoxyisobutyrate, methyl a-ethoxyisobutyrate, and methyl a-ethoxyisobutyrate.
- A-alkoxyisobutyric acid alkyl esters such as ethyl; j8-alkoxyisobutyric acid alkyl esters such as ⁇ -methoxyisobutyric acid, ⁇ -methoxyisobutyric acid, j8-ethoxyisobutyric acid, j8-ethoxyisobutyric acid; and methyl ⁇ -hydroxyisobutyrate; such as ⁇ - hydroxy I Seo acid Echiru alpha - it includes hydroxyisobutyric esters, Tokunihi methoxyisobutyrate methyl butyrate, beta-methoxyisobutyrate methyl butyrate, beta-Etokishiiso methyl butyrate addition Wahi primary hydroxy methyl isobutyrate It can be used.
- the organic semiconductor compound according to the present invention is mixed with the above-mentioned organic solvent, and after forming a film using the prepared solution, the X-ray diffraction spectrum of the obtained film shows a half of the diffraction peak of the maximum intensity. It is characterized in that the value range is 0.4 ° or less, preferably 0.3 ° or less, and more preferably 0.2 ° or less.
- the high crystallinity of a compound can be estimated from the half width power of a diffraction peak in an X-ray diffraction spectrum, and the material power in which molecules are regularly arranged in a wide range has a very small half width. A diffraction peak is obtained.
- the X-ray diffraction spectrum measurement according to the present invention is performed under the following apparatus and under the following measurement conditions.
- the substrate (base) used for the X-ray diffraction measurement of the organic thin film of the present invention and the organic thin-film transistor of the present invention may be the same or different, but a smaller value is obtained as the half-width of the maximum intensity obtained from the obtained X-ray diffraction spectrum.
- the obtained data is used as “half-width of the diffraction peak of the maximum intensity in the X-ray diffraction pattern of the film” according to the present invention.
- the thickness of the thin film used in the measurement is in the range of 5 nm to 100 nm, and preferably, ⁇ ! ⁇ 50 nm.
- the background is taken on the low-angle and wide-angle sides of the diffraction peak, and the sum of the intensities of the respective measurement points above the background is obtained, and this is defined as the peak area.
- the highest intensity of each measurement point is defined as the peak height, and the half width is calculated by the following formula.
- Half width SF X area Z height
- SF a constant related to the peak shape, set to 0.85 in the present invention.
- a film used for X-ray diffraction measurement is formed by coating an organic semiconductor solution in which an organic semiconductor compound is dissolved using an organic solvent or the like on a base such as a substrate, and then heating the solvent by a method such as heating. It can be obtained by vaporizing.
- Methods for coating the organic semiconductor-containing solution on the base include coating, spraying, and directly contacting the base with the solution.Specifically, casting, spin coating, dip coating, screen printing, ink jet printing, etc. And a known method such as blade coating.
- Such an operation can be performed in the air or in an atmosphere of an inert gas such as nitrogen or argon.
- an inert gas such as nitrogen or argon.
- the base temperature when evaporating the solvent, the base temperature, atmospheric pressure, temperature, etc. It is also possible to control.
- the organic semiconductor thin film formed on the base by these methods is further subjected to treatment such as heating and cooling, application of an electric field, a magnetic field, a temperature gradient, and the like, pressurization, friction, and the like, whereby the orientation in the film is improved. It is possible to improve.
- the thickness of the organic semiconductor thin film to be formed is not limited, but is preferably lOOnm or less.
- the base used is not limited, and may be anything such as a Si substrate, a glass substrate, or a polymer film.
- the surface of the base serving as a boundary between the base and the organic semiconductor thin film may be treated by known means such as a thermal oxidation film, or may be surface-modified by treatment using an alkyltrichlorosilane or the like. Well.
- the molecular weight (weight average molecular weight) of the organic semiconductor compound according to the present invention is preferably 10,000 or less, more preferably 100 to 5,000. Furthermore, the ratio (molecular weight distribution) between the weight average molecular weight (Mw) and the number average molecular weight (Mn) according to the present invention is preferably 2 or less.
- the weight average molecular weight (Mw) and number average molecular weight (Mn) of the organic semiconductor compound of the present invention are measured by using GPC (gel permeation chromatography) using THF (tetrahydrofuran) as a column solvent. Perform the measurement.
- GPC measurement conditions are as follows: the column is stabilized at 40 ° C., THF is flowed at a flow rate of 1 ml per minute, and about 100 1 of a sample having a concentration of 1 mg Zml is injected for measurement.
- the column it is preferable to use a commercially available polystyrene die column in combination.
- a refractive index detector (RI detector) or a UV detector is preferably used.
- the molecular weight distribution of the sample is calculated using a calibration curve created using monodispersed polystyrene standard particles. It is preferable to use about 10 points as polystyrene for preparing a calibration curve.
- the molecular weight was measured under the following measurement conditions.
- HLC-8020 manufactured by Tosoh Corporation
- the content of the organic semiconductor conjugate in the organic semiconductor film is preferably 95% by mass or more, more preferably 98% by mass or more. Also, do not affect the characteristics of the organic thin film transistor of the present invention!
- specific compounds of the organic semiconductor compound according to the present invention may be the same compound or a mixture of a plurality of compounds having different structures, which will be described later.
- the content of the organic semiconductor compound was determined by using HPLC (high performance liquid chromatography).
- the following shows the measuring device and the measuring conditions.
- HPLC apparatus GULLIVER manufactured by JASCO Corporation
- a ⁇ -conjugated compound can be preferably used, and further, a compound having the following characteristics is preferably used.
- the organic semiconductor compound is a ⁇ -conjugated compound containing two or more aromatic rings.
- the aromatic ring means any one of an aromatic hydrocarbon ring, an aromatic heterocycle, and an aromatic condensed ring.
- the aromatic rings contained therein may be the same or different.
- the ⁇ -conjugated compound has two or more aromatic hydrocarbon rings or two or more aromatic heterocycles as a partial structure.
- the ⁇ -conjugated compound has at least three types of aromatic hydrocarbon rings or at least three types of aromatic heterocycles as a partial structure.
- the ⁇ -conjugated compound according to (a), (b) or (c) is an unsubstituted aromatic hydrocarbon ring having no condensed ring or an unsubstituted aromatic It has a heterocycle as a partial structure.
- the ⁇ -conjugated compound according to the present invention is required as the above-mentioned organic semiconductor conjugate under the following conditions (soluble at room temperature in an organic solvent, the half-width of the maximum intensity of the X-ray diffraction spectrum of the formed film is 0%). (4 ° or less), a conventionally known semiconductor material may be used.
- acenes such as pentacene-tetracene, phthalocyanines including lead phthalocyanine, low molecular weight compounds such as perylene and its tetracarboxylic acid derivative, thiophene hexamers called hexenyl or sexityofen, and fluorene oligomers
- Aromatic oligomers furthermore, conjugated polymers such as polythiophene, polychelenvinylene, poly ⁇ -phen-lenbilene, and the like can be given.
- the ⁇ according to the present invention is preferred.
- the conjugated compound is preferably a ⁇ -conjugated compound containing two or more aromatic rings. Further, the conjugated compound which satisfies the requirement described in (b) or (c) above, It is preferable to use a minor compound.
- the ⁇ -conjugated compound according to the present invention preferably has two or more aromatic hydrocarbon rings or two or more aromatic heterocycles as a partial structure.
- the aromatic hydrocarbon ring includes a benzene ring, a biphenyl ring, a naphthalene ring, an azulene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a thalicene ring, a naphthacene ring, a triphenylene ring, —Tenorefe-nore ring, m-tenorefe-nore ring, p-tenorefe-nore ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphene ring, picene ring, Examples include a pyrene ring, a pyranthrene ring, and an anthranthrene ring. Further, it has
- Examples of the aromatic heterocyclic ring include a furan ring, a thiophene ring, an oxazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a benzimidazole ring, an oxadiazole ring, a triazole ring, an imidazole ring, Pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, carbazole ring, carbolin ring, diaza lvazole ring (carboline ring Represents a ring in which one of the carbon atoms of the hydrocarbon ring constituting the ring is further substituted with a nitrogen
- the organic semiconductor compound according to the present invention was prepared by a normal pressure process such as coating and printing.
- a thin film can be formed on a variety of substrates (which may be a substrate constituting an organic thin film transistor or another substrate), that is, a thin film transistor which is not a conventionally known organic semiconductor can be manufactured.
- the thiophene oligomer according to the present invention will be described.
- the thiophene oligomer according to the present invention has a partial structure in which at least two or more thiophene ring repeating units having a substituent and at least two or more unsubstituted thiophene ring repeating units are continuous. And the number of thiophene rings contained in the thiophene oligomer is 3 to 40. Is preferably in the range of 3 to 20. More preferably, it is in the range of 4 to 10. More preferably, the thiophene oligomer has a partial structure represented by the general formula (1).
- the thiophene oligomer represented by the general formula (1) according to the present invention will be described.
- examples of the substituent represented by R include an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, Hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (eg, buryl group, aryl group, etc.) ), An alkyl group (eg, ethynyl group, propargyl group, etc.), an aryl group (eg, phenyl group, p-chlorophenyl group, mesityl group, tolyl group, xylyl group, naphthyl group, An alkyl group (
- a preferred substituent is an alkyl group, and more preferably a substituent having 2 to 2 carbon atoms.
- the terminal group of the thiophene oligomer according to the present invention will be described.
- the terminal group of the thiophene oligomer according to the present invention preferably does not have a chain group, and a preferable group as the terminal group is an aryl group (for example, a phenyl group, p -Chlorophenyl group, mesityl group, tolyl group, xylyl group, naphthyl group, anthryl group, azulyl group, acenaphthenyl group, fluoryl group, phenanthryl group, indul group, pyrenyl group, biphenyl group, etc.)
- An alkyl group for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.
- the thiophene oligomer according to the present invention preferably has a Head-to-Tail structure or a Head-to-Tail structure in the structure, in addition to the fact that the structure preferably does not have a Head-to-Head structure.
- head-to-head structure head-to-tail structure, and tail-to-tail structure according to the present invention are described in, for example, "Pi-Organic Organic Solids” (published by Gakkai Shuppan Center in 1998. This can be referred to on pages 27-32, Adv. Mater. 1998, 10, No. 2, pages 93-116, etc.
- specific structural features are shown below.
- the present invention is not limited to these examples showing specific examples of the thiophene oligomer according to the present invention.
- Organic thin film transistor also referred to as organic TFT
- organic thin film transistor organic TFT
- the organic semiconductor thin film according to the present invention when used in an organic thin film transistor (organic TFT), can provide an organic TFT that can drive well.
- An organic TFT organic thin film transistor
- An organic TFT has a top electrode having a source electrode and a drain electrode connected by an organic semiconductor channel as a semiconductor layer on a support, and having a gate electrode thereon via a gate insulating layer.
- a bottom-gate type which has a gate electrode on the support, and has a source electrode and a drain electrode connected by an organic semiconductor channel via a gate insulating layer.
- the thiophene oligomer can be installed on the substrate by vacuum deposition.
- the thiophene oligomer is prepared by dissolving in an appropriate solvent and adding an additive as needed. It is preferable that the solution obtained is set on a substrate by cast coating, spin coating, printing, an inkjet method, an abrasion method, or the like.
- the solvent for dissolving the organic semiconductor compound according to the present invention is not particularly limited as long as the solvent can dissolve the organic semiconductor compound to prepare a solution having an appropriate concentration.
- chain ether solvents such as getyl ether and diisopropyl ether, cyclic ether solvents such as tetrahydrofuran and dioxane, acetone and methylethyl Ketone solvents such as ketones, halogenated alkyl solvents such as chloroform and 1,2-dichloroethane, aromatic solvents such as toluene, o-dichlorobenzene, nitrobenzene, m-talesol, N-methylpyrrolidone; 2 Sulfur carbon and the like.
- the material forming the source electrode, the drain electrode, and the gate electrode is not particularly limited as long as it is a conductive material, and platinum, gold, silver, nickel, chromium, copper, iron, tin, Antimony tin, tantalum, indium, palladium, tellurium, rhenium, iridium, anolemmium, ruthenium, germanium, molybdenum, tungsten, tin oxide 'antimony, indium' tin (ITO), fluorine-doped zinc oxide, zinc , Carbon, graphite, glassy carbon, silver paste and carbon paste, lithium, beryllium, sodium, magnesium, potassium, calcium, scandium, titanium, manganese, zirconium, gallium, niobium, sodium, sodium-potassium alloy, magnesium, Lithium, Anoremi-Pam, Ma Nesium Z-copper mixture, magnesium Z-silver mixture, magnesium Z-aluminum mixture, magnesium Z-indium
- a known conductive polymer whose conductivity has been improved by doping or the like, for example, a conductive polyaline, a conductive polypyrrole, a conductive polythiophene, a complex of polyethylenedioxythiophene and polystyrene sulfonic acid, etc., is preferably used.
- a conductive polyaline a conductive polypyrrole, a conductive polythiophene, a complex of polyethylenedioxythiophene and polystyrene sulfonic acid, etc.
- a method of forming an electrode a method of forming an electrode using a known photolithographic method or a lift-off method on a conductive thin film formed by using the above materials as a raw material by vapor deposition, sputtering, or the like; There is a method of etching using a resist by thermal transfer, ink jet, or the like on the metal foil.
- a conductive polymer solution or dispersion, or a conductive fine particle dispersion may be directly patterned by ink jetting, or may be formed from a coating film by lithography or laser ablation.
- a method of patterning an ink containing a conductive polymer or conductive fine particles, a conductive paste, or the like by a printing method such as letterpress, intaglio, lithographic, or screen printing can also be used.
- Inorganic oxides include silicon oxide, aluminum oxide, tantalum oxide, titanium oxide, tin oxide, vanadium oxide, barium strontium titanate, barium zirconate titanate, lead zirconate titanate, and titanate.
- Examples thereof include lead lanthanum, strontium titanate, barium titanate, barium magnesium fluoride, bismuth titanate, strontium bismuth titanate, strontium bismuth tantanoleate, bismuth niobate tantalate and yttrium trioxide.
- preferred are Sidani silicon, Sidani aluminum, Tidani tantalum and Tidani titanium.
- Inorganic nitrides such as silicon nitride and aluminum nitride can also be suitably used.
- Examples of the method of forming the film include vacuum deposition, molecular beam epitaxy, ion cluster beam, low energy ion beam, ion plating, CVD, sputtering, and atmospheric pressure plasma. Dry process, application method such as spray coating method, spin coating method, blade coating method, dip coating method, casting method, roll coating method, bar coating method, die coating method, etc. And a wet process according to the material.
- the wet process includes a method of applying and drying a liquid in which fine particles of an inorganic oxide are dispersed in an optional organic solvent or water using a dispersing aid such as a surfactant as necessary.
- a so-called sol-gel method of applying and drying a solution of an alkoxide body is used.
- the atmospheric pressure plasma method and the sol-gel method are preferred.
- a method for forming an insulating film by plasma film formation under atmospheric pressure is a process in which discharge is performed under atmospheric pressure or a pressure close to atmospheric pressure, a reactive gas is plasma-excited, and a thin film is formed on a substrate.
- the method is described in JP-A-11-61406, JP-A-11133205, JP-A-2000-121804, JP-A-2000-147209, JP-A-2000-185362, etc. , Atmospheric pressure plasma method).
- a highly functional thin film can be formed with high productivity.
- Examples of the organic compound film include polyimide, polyamide, polyester, polyatarylate, a photo-curable resin of a photo-radical polymerization system, a photo-thion polymerization system, or a copolymer containing an acrylonitrile component; Phenol, polyvinyl alcohol, novolak resin, cyanoethyl pullulan, and the like can also be used.
- Organic compound film formation method Is preferably the wet process.
- the inorganic oxide film and the organic oxide film can be laminated and used together. The thickness of these insulating films is generally 50 ⁇ ! 33 m, preferably 100 nm to 1 ⁇ m.
- the support is made of glass or a flexible resin sheet.
- a plastic film can be used as the sheet.
- the plastic film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylenesulfide, polyarylate, polyimide, and polycarbonate.
- PC polyethylene terephthalate
- PEN polyethylene naphthalate
- PES polyethersulfone
- PC polyetherimide
- polyetherketone polyetherketone
- polyphenylenesulfide polyarylate
- polyimide polyarylate
- PC polycarbonate
- PC cellulose triacetate
- CAP cellulose acetate propionate
- organic thin film transistor using an organic thin film formed using the organic semiconductor conjugate according to the present invention will be described.
- FIG. 1 is a diagram showing a configuration example of an organic TFT according to the present invention.
- FIG. 3A shows that a source electrode 2 and a drain electrode 3 are formed on a support 6 by a metal foil or the like, and an organic semiconductor layer 1 made of an organic thin film transistor material of the present invention is formed between both electrodes.
- An insulating layer 5 is formed thereon, and a gate electrode 4 is further formed thereon to form a field effect transistor.
- FIG. 2B shows the organic semiconductor layer 1 formed between the electrodes in FIG. 2A and formed so as to cover the entire surface of the electrodes and the support using a coating method or the like.
- (C) shows a structure in which the organic semiconductor layer 1 is first formed on the support 6 by a coating method or the like, and then the source electrode 2, the drain electrode 3, the insulating layer 5, and the gate electrode 4 are formed.
- FIG. 11 (d) shows that after forming a gate electrode 4 on a support 6 with a metal foil or the like, an insulating layer 5 is formed, and a source electrode 2 and a drain electrode 3 are formed on the insulating layer 5 with a metal foil or the like.
- the organic semiconductor layer 1 formed of the organic thin film transistor material of the present invention is formed between the electrodes.
- FIG. 2 is a diagram showing an example of a schematic equivalent circuit diagram of an organic TFT sheet.
- the organic TFT sheet 10 has a large number of organic TFTs 11 arranged in a matrix. 7 is each TF Reference numeral 8 denotes a gate bus line of Ti1, and 8 denotes a source bus line of each TFT 11.
- An output element 12 is connected to a source electrode of each TFT 11, and the output element 12 is, for example, a liquid crystal or an electrophoretic element, and constitutes a pixel in a display device.
- the pixel electrode may be used as an input electrode of an optical sensor.
- the output element is shown by an equivalent circuit including a liquid crystal force resistance and a capacitor force. 13 is a storage capacitor, 14 is a vertical drive circuit, and 15 is a horizontal drive circuit.
- the organic EL device of the present invention includes, for example, a device in which an organic EL layer (also referred to as an organic compound layer) is sandwiched between an anode and a cathode. It can be manufactured using the material of the organic EL layer. For example, reference can be made to Nature, 395, pp. 151-154.
- the organic EL device of the present invention is made to emit light (for example, applied to a display device, a lighting device, and the like), from the viewpoint of obtaining effects such as high emission luminance and long light emission life, It is preferable to include the organic semiconductor device of the present invention or the organic thin film transistor of the present invention.
- the coating was applied to the surface of the thermal oxidation film (silicon oxide film) using an applicator under a nitrogen gas atmosphere of 1.013 ⁇ 10 2 kPa, and dried at room temperature. At this time, the thickness of the semiconductor layer was 20 nm.
- the organic thin-film transistor 1 satisfactorily operated as a p-channel enhancement-type TFT.
- the saturation region force of the IV characteristic was also determined to be the carrier mobility. As a result, it was 0.10 cm 2 ZV's.
- the thickness of the semiconductor layer was 20 nm.
- Heat treatment was performed for 2 and 30 minutes. At this time, the thickness of the semiconductor layer was 20 nm.
- a 200-nm-thick thermal oxide film was formed on a Si wafer with a specific resistance of 0.02 ⁇ 'cm as a gate electrode to form a gate electrode.
- the solution was applied to the surface of the thermal oxidation film (oxygen silicon film) using an applicator under a nitrogen gas atmosphere of 1.013 ⁇ 10 2 kPa, and dried at room temperature. I let it.
- the thickness of the semiconductor layer was 20 nm.
- the thickness of the semiconductor layer was 20 nm.
- the obtained thin film was evaluated by X-ray diffraction. As a result, the half value width of the 18.2A diffraction peak showing the maximum intensity was 0.4 °.
- the surface of the gate insulating film subjected to the surface treatment was applied in an atmosphere of two gases using an applicator, and dried at room temperature. At this time, the thickness of the semiconductor layer was 20 nm.
- the organic TFT element of the present invention exhibits excellent transistor characteristics immediately after fabrication and excellent transistor characteristics of high carrier mobility as compared with the comparative organic TFT element. You can see that.
- a top emission type organic EL device having a sealing structure as shown in FIG. 7 was prepared with reference to the method described in Nature, Vol. 395, pp. 151-154.
- 101 is a substrate
- 102a is an anode
- 102b is an organic EL layer (specifically, an electron transport layer, a light emitting layer, a hole transport layer, etc. are included)
- 102c is a cathode
- 102a is a cathode.
- the light emitting element 102 is formed by the organic EL layer 102b and the cathode 102c.
- 103 denotes a sealing film.
- the organic EL device of the present invention may be either a bottom emission type or a top emission type.
- the organic EL device of the present invention and the organic thin film transistor of the present invention (here, the organic thin film of the present invention A transistor is used as a switching transistor, a driving transistor, or the like) to produce an active matrix light-emitting element.
- the organic thin film of the present invention A transistor is used as a switching transistor, a driving transistor, or the like to produce an active matrix light-emitting element.
- a mode in which a substrate on which a thin film transistor 602 is formed is used.
- a known method of manufacturing a TFT can be referred to.
- the TFT may be a conventionally known top gate type TFT or a bottom gate type TFT.
- the organic EL device produced as described above exhibited good light emission characteristics in various light emission modes such as monochromatic, full color, and white.
Abstract
Description
Claims
Priority Applications (3)
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US11/628,695 US20080048181A1 (en) | 2004-06-10 | 2005-06-06 | Organic Semiconductor Thin Film, Organic Semiconductor Device, Organic Thin Film Transistor and Organic Electronic Luminescence Element |
EP05750987A EP1758172A1 (en) | 2004-06-10 | 2005-06-06 | Organic semiconductor thin film, organic semiconductor device, organic thin film transistor, and organic electro-luminescence element |
JP2006514489A JPWO2005122278A1 (ja) | 2004-06-10 | 2005-06-06 | 有機半導体薄膜、有機半導体デバイス、有機薄膜トランジスタ及び有機エレクトロルミネッセンス素子 |
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WO2008093663A1 (ja) * | 2007-01-31 | 2008-08-07 | Konica Minolta Holdings, Inc. | 有機薄膜トランジスタ、その製造方法及び有機半導体デバイス |
JP2008287928A (ja) * | 2007-05-15 | 2008-11-27 | Mitsubishi Chemicals Corp | RuTe2を含む燃料電池用触媒と、この燃料電池用触媒を用いた燃料電池用電極材料及び燃料電池 |
US20080315186A1 (en) * | 2006-03-10 | 2008-12-25 | Sony Corporation | Organic Semiconductor Device and Organic Semiconductor Thin Film |
WO2009069687A1 (ja) * | 2007-11-30 | 2009-06-04 | Osaka University | 共役系化合物、含窒素縮合環化合物、含窒素縮合環重合体、有機薄膜及び有機薄膜素子 |
EP2113944A1 (en) * | 2007-02-23 | 2009-11-04 | Konica Minolta Holdings, Inc. | Organic thin film transistor and method for manufacturing organic thin film transistor |
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JP2008255097A (ja) * | 2007-03-09 | 2008-10-23 | Sumitomo Chemical Co Ltd | 含フッ素多環芳香族化合物、含フッ素重合体、有機薄膜及び有機薄膜素子 |
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- 2005-06-06 US US11/628,695 patent/US20080048181A1/en not_active Abandoned
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US20080315186A1 (en) * | 2006-03-10 | 2008-12-25 | Sony Corporation | Organic Semiconductor Device and Organic Semiconductor Thin Film |
WO2008093663A1 (ja) * | 2007-01-31 | 2008-08-07 | Konica Minolta Holdings, Inc. | 有機薄膜トランジスタ、その製造方法及び有機半導体デバイス |
JPWO2008093663A1 (ja) * | 2007-01-31 | 2010-05-20 | コニカミノルタホールディングス株式会社 | 有機薄膜トランジスタ、その製造方法及び有機半導体デバイス |
EP2113944A1 (en) * | 2007-02-23 | 2009-11-04 | Konica Minolta Holdings, Inc. | Organic thin film transistor and method for manufacturing organic thin film transistor |
EP2113944A4 (en) * | 2007-02-23 | 2012-08-22 | Konica Minolta Holdings Inc | ORGANIC THIN FILM TRANSISTOR AND METHOD FOR MANUFACTURING ORGANIC THIN FILM TRANSISTOR |
JP2008287928A (ja) * | 2007-05-15 | 2008-11-27 | Mitsubishi Chemicals Corp | RuTe2を含む燃料電池用触媒と、この燃料電池用触媒を用いた燃料電池用電極材料及び燃料電池 |
WO2009069687A1 (ja) * | 2007-11-30 | 2009-06-04 | Osaka University | 共役系化合物、含窒素縮合環化合物、含窒素縮合環重合体、有機薄膜及び有機薄膜素子 |
US8378338B2 (en) | 2007-11-30 | 2013-02-19 | Sumitomo Chemical Company, Limited | Conjugated compound, nitrogenated condensed-ring compound, nitrogenated condensed-ring polymer, organic thin film, and organic thin film element |
US9812657B2 (en) | 2014-01-07 | 2017-11-07 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
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JPWO2005122278A1 (ja) | 2008-04-10 |
US20080048181A1 (en) | 2008-02-28 |
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