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WO2007123030A1 - Matériau semi-conducteur organique, couche semi-conductrice organique, dispositif semi-conducteur organique, et transistor à couche mince organique - Google Patents

Matériau semi-conducteur organique, couche semi-conductrice organique, dispositif semi-conducteur organique, et transistor à couche mince organique Download PDF

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Publication number
WO2007123030A1
WO2007123030A1 PCT/JP2007/057956 JP2007057956W WO2007123030A1 WO 2007123030 A1 WO2007123030 A1 WO 2007123030A1 JP 2007057956 W JP2007057956 W JP 2007057956W WO 2007123030 A1 WO2007123030 A1 WO 2007123030A1
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group
organic semiconductor
general formula
semiconductor material
organic
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PCT/JP2007/057956
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English (en)
Japanese (ja)
Inventor
Rie Katakura
Hidekane Ozeki
Yasushi Okubo
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Konica Minolta Holdings, Inc.
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Publication of WO2007123030A1 publication Critical patent/WO2007123030A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
    • C07C15/62—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing four rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • 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
    • H10K19/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic element specially adapted for rectifying, amplifying, oscillating or switching, covered by group H10K10/00
    • H10K19/10—Integrated devices, or assemblies of multiple devices, comprising at least one organic element specially adapted for rectifying, amplifying, oscillating or switching, covered by group H10K10/00 comprising field-effect transistors

Definitions

  • Organic semiconductor materials organic semiconductor films, organic semiconductor devices, and organic thin film transistors
  • the present invention relates to an organic semiconductor material, an organic semiconductor film, an organic semiconductor device, and an organic thin film transistor.
  • a display medium is formed by using elements utilizing liquid crystal, organic EL (organic electoluminescence), electrophoresis, or the like.
  • a technology using an active drive element (TFT element) as an image drive element has become mainstream to ensure uniformity of screen brightness, screen rewriting speed, and the like!
  • TFT element active drive element
  • these TFT elements are formed on a glass substrate, and liquid crystal, organic EL elements, etc. are sealed.
  • TFT elements such as a—Si (amorphous silicon) and p—Si (polysilicon) can be mainly used for TFT elements, and these S ⁇ conductors (and metal films as required).
  • the TFT element is manufactured by forming a multi-layered structure and sequentially forming source, drain, and gate electrodes on the substrate. The production of such TFT elements usually requires sputtering and other vacuum-based manufacturing processes.
  • the substrate material is limited to a material that can withstand the process temperature. Become. For this reason, in practice, glass must be used, and when the above-mentioned electronic paper or digital paper! /, And a thin display using such a conventionally known TFT element are used, the display Will be heavy and inflexible, and may be broken by the impact of a drop.
  • a TFT element is formed on a transparent resin substrate and the display material can be driven by the TFT element, the display will be lighter and more flexible than conventional ones, and will not crack even if dropped. Will be difficult to crack))
  • the acenes such as pentacene and tetracene have been studied so far (see, for example, Patent Document 1), and phthalocyanines including lead phthalocyanine.
  • Low molecular weight compounds such as perylene and its tetracarboxylic acid derivatives (see, for example, Patent Document 2), and aromatic oligomers typically represented by thiophene hexamer called oc-chenyl or sexithiophene (for example, see Patent Document 3) ), Naphthalene, anthracene and a compound in which a 5-membered aromatic heterocyclic ring is condensed symmetrically (for example, see Patent Document 4), a modified oligo and a polydithienopyridine (for example, see Patent Document 5), Polythiophene, polyethylene biylene, poly-p-phenylene birene, and conjugated polymers are limited. A material exhibiting sufficient carrier mobility and ONZOFF ratio has been found while maintaining sufficient solubility in a solvent that can only be achieved with other types of compounds (for example, see Non-Patent Documents 1 to 3). Nah ...
  • acene compounds such as rubrene and pentacene are easily oxidized by air and converted into oxidants and dimers such as endoperoxide, and as field effect transistors. It is known that the performance is greatly deteriorated, and there are still problems to be solved regarding the storage stability in solution and the stability of the coating film.
  • acene-based compounds that are relatively stable with respect to acids include some compounds that are substituted with silylethynyl groups at positions 6 and 13 of pentacene and positions 5 and 11 of anthradithiophene. (For example, see non-patent documents 5, 6, 7 and patent document 7.)
  • a novel charge transporting material that is dissolved in a solvent having process suitability at a high concentration, has sufficient carrier mobility, onZoff ratio, and further has stability in a solution state.
  • the development of a semiconducting composition using bismuth is awaited.
  • the compound is not studied as a semiconductor material, and only its usage is illustrated, and sufficient TFT performance is obtained.
  • Patent Document 1 Japanese Patent Laid-Open No. 5-55568
  • Patent Document 2 JP-A-5-190877
  • Patent Document 3 JP-A-8-264805
  • Patent Document 4 JP-A-11-195790
  • Patent Document 5 Japanese Patent Laid-Open No. 2003-155289
  • Patent Document 6 Pamphlet of International Publication No. 03Z016599
  • Patent Document 7 US Pat. No. 6690029 Specification
  • Non-Patent Document 1 Science 289 ⁇ , 599 pages (2000)
  • Non-Patent Document 2 “Nature” 403ature, 521 pages (2000)
  • Non-Patent Document 3 "Advanced Material", 2002, No. 2, page 99
  • Non-Patent Document 4 Science, 2004, 303, 5664, 1644-1646
  • Non-Patent Document 5 Org. Lett., Vol. 4 (2002), p. 15
  • Non-Patent Document 6 J. Am. Chem. Soc., Vol. 127 (2005), p. 4986
  • Non-Patent Document 7 Adv. Mater., Vol. 15 (2003), 2009
  • An object of the present invention is to molecularly design an organic semiconductor material useful for thin film transistor applications, and to use the obtained organic semiconductor material to exhibit high carrier mobility, a high ONZOFF ratio, and high durability ( It is to provide an organic semiconductor film, an organic semiconductor device, and an organic thin film transistor having both oxidation stability and stability over time. Means for solving the problem
  • R represents a hydrogen atom, a halogen atom or a substituent, and a plurality of R may be the same or different. * Represents a bonding site with the aromatic condensed polycycle. ]
  • R and R each represent a hydrogen atom, a halogen atom or a substituent.
  • R and R each represent a hydrogen atom, a halogen atom or a substituent.
  • the aromatic condensed polycycle contains two or more partial structures represented by the general formula (2)
  • R to R each represents a hydrogen atom, a halogen atom or a substituent.
  • nl to n3 are 0
  • [0035] 15 It is formed by dissolving or dispersing the organic semiconductor material according to any one of 1 to 13 above in an organic solvent, and applying and drying the obtained solution or dispersion. An organic semiconductor film.
  • An organic thin film transistor wherein the organic semiconductor material according to any one of 1 to 13 is used for a semiconductor layer.
  • organic semiconductor materials useful for thin film transistor applications are molecularly designed, and the resulting organic semiconductor materials exhibit high carrier mobility, a high ONZOFF ratio, and high durability ( An organic semiconductor film, an organic semiconductor device, and an organic thin film transistor having both oxidation stability and stability over time have been provided.
  • FIG. 1 is a diagram showing a configuration example of an organic TFT according to the present invention.
  • FIG. 2 is a diagram showing an example of a schematic equivalent circuit diagram of an organic TFT sheet.
  • FIG. 3 is a schematic view showing an example of a display device constituted by an organic EL element cover.
  • FIG. 4 is a schematic diagram of display unit A.
  • FIG. 5 is a schematic diagram of a pixel.
  • organic semiconductor material of the present invention an organic semiconductor material useful for thin film transistor applications was obtained by using the structure defined in any one of claims 1 to 13.
  • organic semiconductor film an organic semiconductor device, and an organic thin film transistor (also referred to as organic TFT) exhibiting high carrier mobility and good ONZOf f characteristics were obtained. .
  • the organic electroluminescence device having the organic TFT of the present invention exhibits good light emission characteristics.
  • the present inventors have an aromatic condensed polycycle in which three or more rings are condensed as a partial structure, and the aromatic condensed polycycle is represented by the above general formula (1
  • an organic semiconductor material containing a compound according to the present invention having three or more substituents represented by (II) has high mobility and high stability against oxidation.
  • the compound according to the present invention has, as a partial structure, an aromatic condensed polycycle having a large ⁇ -conjugated surface that is advantageous for carrier transfer, and further in a solution that is a major problem with the condensed polycyclic compound.
  • the stability of the molecule can be reduced by introducing three or more alkynyl substituents to the extent that it is sufficiently stable against acid. .
  • the alkyl substituent since the alkyl substituent has few elements that inhibit the ⁇ stack between aromatic rings, a highly crystalline film in which molecules are arranged more closely is formed, and as a result, the mobility of the coating film is increased. It is presumed that not only can it be made high, but also deterioration factors such as oxygen and moisture hardly permeate, forming a thin film and improving durability.
  • the compound according to the organic semiconductor material of the present invention has an aromatic condensed polycycle in which three or more rings are condensed as a partial structure.
  • examples of the aromatic condensed polycycle in which three or more rings are condensed include an aromatic hydrocarbon ring and an aromatic heterocycle.
  • aromatic hydrocarbon rings condensed with three or more rings include naphthacene ring, anthracene ring, tetracene ring, pentacene ring, hexacene ring, phenanthrene ring, pyrene ring, benzopyrene ring, benzoazulene ring, and taricene ring.
  • Benzochrysene ring acenaphthene ring, acenaphthylene ring, triphenylene ring, coronene ring, benzocoronene ring, hexabenzocoronene ring, fluorene ring, benzofluorene ring, fluoranthene ring, perylene ring, naphthoperylene ring, pentabenzoperylene ring, benzoperylene Ring, pentaphen ring, picene ring, pyranthrene ring, coronene ring, naphtho coronene ring, ovalene ring, anthraanthrene ring and the like.
  • These rings may have a substituent represented by R in the general formula (1) described later.
  • the aromatic heterocycle condensed with 3 or more rings is preferably an aromatic heterofused ring containing a hetero atom selected from N, O and S as an element constituting the condensed ring.
  • a hetero atom selected from N, O and S as an element constituting the condensed ring.
  • atalidine ring benzoquinoline ring, force rubazole ring, phenazine ring, phenanthridine ring, phenanthorin ring, canoleporin ring, cyclazine ring, kindlin ring, thebesin ring, cundrin ring, triphenodithiazine ring , Triphenodioxazine ring, phenanthrazine ring, acrindrin ring, anthrazine ring, perimidine ring, diazacarbazole ring (representing any one of the carbon atoms constituting the carboline ring replaced by a nitrogen atom), Phosphorus ring
  • these condensed aromatic rings are more condensed than peri condensed rings (condensed rings having atoms shared as the vertices of the three aromatic rings among the elements constituting the condensed aromatic rings). It is preferable that the ring is a condensed ring in which an aromatic ring shared by the vertices of the three aromatic rings is linearly extended. It is preferable that the acene series (condensed ring in which the aromatic rings are condensed in a straight line) is preferable to the condensed ring of the condensed ring).
  • aromatic condensed polycycle according to the present invention is preferably those in which 3 to 8 rings are condensed, and more preferably those in which 4 to 7 rings are condensed.
  • the substituent represented by R includes an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert butyl group, a pentyl group).
  • an alkyl group for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert butyl group, a pentyl group.
  • An aromatic hydrocarbon ring or an aromatic heterocyclic ring which may have a substituent) or a phosphono group may have a substituent or a phosphono group.
  • substituents may be further substituted, or a plurality of these substituents may be bonded to each other to form a ring.
  • the aromatic condensed polycycle according to the present invention has a plurality of substituents represented by the general formula (1), the substituents represented by R of the substituents may be the same or different. May be.
  • the aromatic condensed polycycle in which three or more rings are condensed as a partial structure has three substituents represented by the general formula (1).
  • the above-mentioned compounds form a film with higher crystallinity, and as a result, not only can the mobility of the coating film be increased, but also a thin film that is difficult to permeate deterioration factors such as oxygen and moisture, resulting in durability (acid ⁇ stability and It is estimated that the stability over time) was improved.
  • preferred embodiments of the compound according to the present invention are as follows (a), (b), (c) or (d):
  • a kill group a cycloalkyl group, an alkyl group, an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, Si () or Ge () (where represents a substituent).
  • Aromatic hydrocarbon group aromatic heterocyclic group, Si () or Ge O ⁇ ) (where R 'is
  • R and R in the general formula (2) and R to R 1S in the general formula (3) are each represented by the same substituent.
  • the embodiment of the compound according to the present invention is represented by the following (e), (f), (g), (h) or (i).
  • the substituted position of the substituted fur group may be 3,4-substituted or 3,4,5-substituted, and the substituent is preferably an alkyl group, an alkoxy group or a phenyl group.
  • the organic semiconductor material of the present invention containing a compound having three or more substituents represented by the general formula (1) has high durability (oxidation stability and stability over time). In addition, it has become possible to provide materials with high carrier mobility.
  • the compound according to the organic semiconductor material of the present invention can be synthesized by referring to a conventionally known synthesis method.
  • a synthesis example of the exemplified compound 1 given as a specific example above is an example. As shown.
  • the organic semiconductor material of the present invention can be mixed with an appropriate organic solvent (described later) and used as a solution or a dispersion.
  • any organic solvent may be used, and two or more organic solvents may be mixed and used.
  • the composition preferably contains at least one non-halogen solvent, and more preferably comprises only a non-halogen solvent.
  • the organic semiconductor film of the present invention is preferably produced through a step of forming a film using a solution or dispersion at room temperature prepared by mixing the organic semiconductor material of the present invention with the organic solvent shown below.
  • a solution or dispersion at room temperature is preferably a dispersion in which a solution or dispersion is formed when an organic semiconductor material and an organic solvent are mixed under conditions of 10 ° C to 80 ° C.
  • the liquid represents a state in which the organic semiconductor material is dispersed in the form of particles, but includes a state in which the organic semiconductor material is partially dissolved in the dispersion.
  • the dispersion for example, it dissolves under a temperature condition of 80 ° C to form a solution, but when returned to room temperature (usually showing a temperature of around 25 ° C), the organic semiconductor material The particles, aggregates, precipitates and the like are dispersed in an organic solvent.
  • the organic solvent used for the preparation of the above solution or dispersion may be a single solvent or a mixed solvent without particular limitation, but preferably a non-halogen solvent is used.
  • Non-halogen solvents 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 and dioxane.
  • Ether solvents such as ethylene glycol jetyl ether, anisole, benzeno retinore ethere, ethino refenore enore, diphene nore ethenore, methino tert-butyl ether, etc., ester solvents such as methyl acetate, ethyl acetate, ethilce mouth solve , Alcohol solvents such as methanol, ethanol and isopropanol, ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, 2-hexanone, 2-heptanone and 3-heptanone, other dimethylformamide, dimethylsulfoxide Sid, Jetylform Amides, 1,3 dioxolane and the like.
  • Alcohol solvents such as methanol, ethanol and isopropanol
  • ketone solvents such as acetone, methyl ethyl ketone, cyclohexan
  • the organic solvent used in combination is not particularly limited, but preferable ones are methanol, ethanol, isopropanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, pyrrolidone, N-methylpyrrolidone, dimethyl.
  • oxyisobutyric acid alkyl ester may be used.
  • oxyisobutyric acid ester methyl ⁇ -methoxyisobutyrate, ethyl a-methoxyisobutyrate, methyl a-ethoxyisobutyrate, a-ethoxyisobutyric acid
  • A-alkoxyisobutyric acid alkyl esters such as ethyl
  • j8-alkoxyisobutyric acid alkyl esters such as methyl ⁇ -methoxyisobutyrate, ethyl ⁇ -methoxyisobutyrate, methyl j8-ethoxyisobutyrate, j8-ethoxyisobutyrate; and methyl ⁇ -hydroxyisobutyrate; such as ⁇ - hydroxy I Seo acid Echiru alpha - it includes hydroxyisobutyric esters, Tokunihi methoxyisobutyrate, Tokuni
  • Organic semiconductor device organic thin film transistor (also called organic TFT) >>
  • organic semiconductor device and organic thin film transistor also referred to as organic TFT in the present application
  • organic TFT organic thin film transistor
  • the organic semiconductor material of the present invention provides an organic semiconductor device and an organic TFT that drive well when used in a semiconductor layer such as an organic semiconductor film, an organic semiconductor device, and an organic thin film transistor (organic TFT). can do.
  • An organic TFT (organic thin film transistor) has a source electrode and a drain electrode connected by an organic semiconductor channel as a semiconductor layer on a support, and a top having a gate electrode on the gate electrode via a gate insulating layer.
  • a gate type and a bottom gate type having a gate electrode on a support and a source electrode and a drain electrode connected by an organic semiconductor channel through a gate insulating layer are roughly classified.
  • the organic semiconductor material of the present invention in the semiconductor layer of the organic TFT, it can be installed on the substrate by vacuum deposition, but it is dissolved in an appropriate solvent and an additive is added as necessary. It is preferable to place the prepared solution on the substrate by cast coating, spin coating, printing, inkjet method, abrasion method, etc.
  • the solvent for dissolving the organic semiconductor compound according to the present invention is not particularly limited as long as the organic semiconductor compound can be dissolved to prepare a solution with an appropriate concentration.
  • chain ether solvents such as jetyl ether and diisopropyl ether, cyclic ether solvents such as tetrahydrofuran and dioxane, ketone solvents such as acetone and methylethyl ketone, halogenated solvents such as chloroform and 1,2-dichloroethane.
  • Alkyl solvents, aromatic solvents such as toluene, o-dichlorobenzene, nitrobenzene, and m-talesol, N-methylpyrrolidone, and carbon dioxide disulfide can be mentioned.
  • a solvent containing a non-halogen solvent is preferable, and a non-halogen solvent is preferable.
  • the material for 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 bell, tantalum, indium, palladium, tellurium, rhenium, iridium, ano-remium, ruthenium, germanium, molybdenum, tungsten, tin oxide 'antimony, indium oxide' 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 monopotassium alloy, magnesium, Lithium, Anoleum, Ma Nesium Z copper mixture, magnesium Z silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z acid-aluminum mixture, lithium Z
  • conductive polymer whose conductivity has been improved by doping or the like, for example, conductive polyarlin, conductive polypyrrole, conductive polythiophene, a complex of polyethylene dioxythiophene and polystyrene sulfonic acid is preferably used. It is done. Among them, those having a low electrical resistance on the contact surface with the semiconductor layer are preferable.
  • a method for forming an electrode a method for forming an electrode using a known photolithographic method or a lift-off method using a conductive thin film formed by a method such as vapor deposition or sputtering using the above as a raw material, aluminum, copper, or the like Resist by thermal transfer, ink jet, etc. on metal foil There is a method of etching using a metal.
  • the conductive polymer solution or dispersion, or the conductive fine particle dispersion may be directly patterned by ink jetting, or may be formed from the 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 relief printing, intaglio printing, lithographic printing, or screen printing can also be used.
  • the gate insulating layer various insulating films can be used.
  • an inorganic oxide film having a high relative dielectric constant is 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, titanate
  • examples include lead lanthanum, strontium titanate, barium titanate, magnesium barium fluoride, bismuth titanate, strontium bismuth titanate, strontium bismuth tantanoate, bismuth tantalate niobate, and yttrium trioxide.
  • acid silicate, acid aluminum, acid tantalum, and acid titanium are preferred.
  • Inorganic nitrides such as silicon nitride and aluminum nitride can also be suitably used.
  • Examples of the film formation method include vacuum deposition, molecular beam epitaxy, ion cluster beam, low energy ion beam, ion plating, CVD, sputtering, and atmospheric pressure plasma. Dry process, spray coating method, spin coating method, blade coating method, dip coating method, casting method, roll coating method, bar coating method, die coating method and other coating methods, printing and ink jet patterning methods, etc. Can be used depending on the material.
  • the wet process includes 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 necessary, or an oxide precursor.
  • a so-called sol-gel method in which a solution of a body, for example, an alkoxide body is applied and dried is used.
  • the atmospheric pressure plasma method and the sol-gel method are preferable.
  • the method of forming an insulating film by plasma film formation under atmospheric pressure is a process in which a thin film is formed on a substrate by discharging at atmospheric pressure or a pressure near atmospheric pressure to excite reactive gas in plasma.
  • the method is disclosed in JP-A-11-61406, JP-A-11-133205, JP-A-2000-121804, JP-A-2000-147209, JP-A-2000-185362. (Hereinafter also referred to as atmospheric pressure plasma method).
  • atmospheric pressure plasma method As a result, a highly functional thin film can be formed with high productivity.
  • organic compound film polyimides, polyamides, polyesters, polyacrylates, photo-radical polymerization-type, photo-powered thione polymerization-type photocurable resins, or copolymers containing acrylonitrile components, polybules.
  • Phenolic alcohol, polybutyl alcohol, novolac resin, cyano ethyl pullulan and the like can also be used.
  • the wet process is preferable.
  • An inorganic oxide film and an organic oxide film can be stacked and used together. The thickness of these insulating films is generally 50 ⁇ ! ⁇ 3 m, preferably 100 nm to l ⁇ m.
  • the support is made of glass or a flexible resin sheet, and for example, a plastic film can be used as the sheet.
  • a plastic film examples include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyethylene-sulfuride, polyarylate, polyimide, polycarbonate ( PC), cellulose triacetate (TAC), and cellulose acetate propionate (CAP).
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PES polyethersulfone
  • polyetherimide polyetheretherketone
  • polyethylene-sulfuride polyarylate
  • PC polycarbonate
  • TAC cellulose triacetate
  • CAP cellulose acetate propionate
  • organic thin film transistor (organic TFT) using an organic thin film formed using the organic semiconductor compound 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.
  • a source electrode 2 and a drain electrode 3 are formed on a support 6 with a metal foil or the like, and an organic semiconductor layer 1 which is the 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. 1A so as to cover the entire surface of the electrode and the support using a coating method or the like.
  • FIG. 4 (C) shows that the organic semiconductor layer 1 is first formed on the support 6 by using 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.
  • the gate electrode 4 is formed on the support 6 with a metal foil or the like, and then the insulating layer 5 is formed thereon.
  • the organic semiconductor layer 1 formed by the organic thin film transistor material of the present invention is formed between the electrodes.
  • Other configurations such as those shown in (e) and (f) of FIG.
  • 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 a gate bus line of each TF T11, and 8 is a source bus line of each TFT11.
  • An output element 12 is connected to the source electrode of each TFT 11, and this output element 12 is, for example, a liquid crystal, an electrophoretic element or the like, and constitutes a pixel in the display device.
  • the pixel electrode may be used as an input electrode of the photosensor.
  • an equivalent circuit including a liquid crystal force resistor and a capacitor force is shown as an output element.
  • 13 is a storage capacitor
  • 14 is a vertical drive circuit
  • 15 is a horizontal drive circuit.
  • the organic TFT using the organic semiconductor material of the present invention can be applied to the technology introduced in, for example, SID2005, sessio n49-1, 2, 3, and an a-Si transistor of the present invention can be applied. Good characteristics can be obtained by replacing it with an organic semiconductor transistor.
  • organic electroluminescent element including the organic TFT of the present invention will be described as an example of technology application.
  • the organic semiconductor device or the organic thin film transistor of the present invention can be provided in an organic electroluminescence element (also referred to as an organic EL element).
  • the organic EL element is, for example, an organic EL layer (organic layer) between an anode and a cathode. Force, which includes a state in which the organic compound layer is sandwiched (also referred to as a sandwiched state).
  • These configurations include a conventionally known layer configuration, a material of an organic EL layer, and the like. I can do it. For example, reference can be made to the literature of Nature, 395, 151-154.
  • the organic semiconductor device of the present invention In emitting light from an organic EL element (for example, applied to a display device, a lighting device, etc.), the organic semiconductor device of the present invention is obtained from the viewpoint of obtaining high light emission luminance and a long light emission lifetime. Alternatively, it is preferable to have the organic thin film transistor of the present invention. [0116] ⁇ Display device ⁇
  • the organic EL element may be used as a kind of lamp such as an illumination or exposure light source, a projection device that projects images, or a display device that directly recognizes still images and moving images (displays) ) May be used.
  • a display device for video playback either the simple matrix (passive matrix) method or the active matrix method may be used.
  • FIG. 3 is a schematic diagram showing an example of a display device configured with organic EL element power.
  • Fig. 11 is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.
  • the display 21 also has a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
  • the control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside. Sequentially emit light according to the image data signal, scan the image, and display the image information on the display unit A.
  • FIG. 4 is a schematic diagram of the display unit A.
  • the display portion A includes a wiring portion including a plurality of scanning lines 25 and data lines 26, a plurality of pixels 23, and the like on a substrate.
  • the light power emitted from the pixel 23 is taken out in the direction of the white arrow (downward).
  • the scanning lines 25 and the plurality of data lines 26 in the wiring portion are each made of a conductive material, and the scanning lines 25 and the data lines 26 are orthogonal to each other in a grid pattern and are connected to the pixels 23 at the orthogonal positions (details). Is not shown).
  • the pixel 23 When a scanning signal is applied from the scanning line 25, the pixel 23 receives an image data signal from the data line 26. And emits light according to the received image data. Full color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
  • FIG. 5 is a schematic diagram of a pixel.
  • the pixel includes an organic EL element 100, a switching transistor 110, a driving transistor 120, a capacitor 130, and the like.
  • Full-color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 100 for a plurality of pixels and arranging them on the same substrate.
  • an image data signal is applied from the control unit B to the drain of the switching transistor 110 via the data line 60.
  • a scanning signal is applied from the control unit B to the gate of the switching transistor 110 via the scanning line 50, the switching transistor 110 is turned on, and the image data signal applied to the drain is driven by the capacitor 130. It is transmitted to the gate of transistor 120.
  • the capacitor 130 By transmitting the image data signal, the capacitor 130 is charged according to the potential of the image data signal, and the drive of the drive transistor 120 is turned on.
  • the drive transistor 120 has a drain connected to the power supply line 7, a source connected to the electrode of the organic EL element 100, and the power supply line 70 to the organic EL element 100 according to the potential of the image data signal applied to the gate. Current is supplied.
  • the driving of the switching transistor 11 is turned off.
  • the capacitor 130 maintains the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied.
  • the organic EL device 10 continues to emit light until it is released.
  • the driving transistor 120 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 100 emits light.
  • the organic EL element 100 emits light by providing a switching transistor 110 and a drive transistor 120 as active elements for the organic EL element 100 of each of a plurality of pixels. Accordingly, each of the organic EL elements 100 provided in the plurality of pixels 23 as shown in FIG. 4 emits light.
  • Such a light emitting method is called an active matrix method.
  • the light emission of the organic EL element 100 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or a predetermined light emission by a binary image data signal.
  • the amount can be on or off.
  • the potential of the capacitor 130 may be maintained until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
  • the present invention not only the active matrix method described above, but also a passive matrix light emission drive in which an organic EL element emits light according to a data signal only when a scanning signal is scanned.
  • a 2000 A thick thermal oxide film was formed on a Si wafer with a specific resistance of 0.01 ⁇ 'cm as the gate electrode to form a gate insulating layer, and then surface treatment with octadecyltrichlorosilane was performed.
  • Comparative Compound 1 (Pentacene, manufactured by Aldrich, used after sublimation purification of a commercially available reagent) was bubbled with nitrogen in a nitrogen atmosphere for 30 minutes. It is dissolved at a concentration of 0.5% by mass in toluene, spin-coated in a nitrogen atmosphere (rotation speed 2500 rpm, 15 seconds), and naturally dried to form a cast film, and then 50 ° in a nitrogen atmosphere. C, heat-treated for 30 minutes.
  • Comparative compound 2 (2, 3, 9, 10-tetrahexylpentacene) was synthesized by the method described in Organic Letters, vol. 2 (2000), p85.
  • Organic thin film transistor 2 was produced in the same manner as in the production of organic thin film transistor 1, except that comparative compound 1 was changed to comparative compound 2.
  • Comparative Compound 3 was synthesized by the method described in J. Am. Chem. Soc., Vol. 127 (2005), ⁇ 4986, supporting information.
  • Organic thin film transistor 3 was produced in the same manner as in the production of organic thin film transistor 1, except that comparative compound 1 was changed to comparative compound 3.
  • Comparative I ⁇ product 4 Comparative I ⁇ product 1 was changed to (rubrene, Aldrich, and was used sublimation purification commercially available reagent) in a similar manner, an organic thin film transistor 4 Produced.
  • Organic thin film transistors 5 to 19 were produced in the same manner as in the production of the organic thin film transistor 2, except that the organic semiconductor material of the present invention described in Table 1 was used instead of the comparative compound 1.
  • the carrier mobility and the ONZOFF value of each element were measured immediately after the element was created.
  • the carrier mobility is obtained from the saturation region of the IV characteristics
  • the ONZOFF ratio is obtained from the ratio of the drain current value when the drain bias is set to 50 V and the gate bias is set to 50 V and OV.
  • organic thin film transistors 5 to 19 fabricated using the organic semiconductor material of the present invention showed excellent characteristics in both carrier mobility and ONZOFF ratio immediately after fabrication, and the mobility was 10 after the durability test. — 2 or more, ON / OFF ratio is 10 5 or more, and there is little deterioration over time.

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

Abstract

La présente invention concerne une conception moléculaire pour un matériau semi-conducteur organique qui est utile pour les transistors à couche mince. Elle concerne également une couche semi-conductrice organique, un dispositif semi-conducteur organique et un transistor à couche mince organique utilisant respectivement le matériau semi-conducteur organique conçu selon l'invention et dont la mobilité de porteurs, le rapport marche/arrêt et la durabilité (stabilité à l'oxydation et stabilité à long terme améliorées) sont élevés. L'invention concerne spécifiquement un matériau semi-conducteur organique contenant un composé comportant une structure partielle composée d'un cycle polycyclique aromatique fusionné, trois cycles ou plus étant fusionnés. Ce matériau semi-conducteur organique est caractérisé en ce que le cycle polycyclique aromatique fusionné comporte trois substituants ou plus représentés par la formule générale (1) suivante.
PCT/JP2007/057956 2006-04-19 2007-04-11 Matériau semi-conducteur organique, couche semi-conductrice organique, dispositif semi-conducteur organique, et transistor à couche mince organique WO2007123030A1 (fr)

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WO2008120839A1 (fr) * 2007-03-30 2008-10-09 Gyeongsang National University Industrial And Academic Collaboration Foundation Nouveau composé semi-conducteur organique et transistor à couches minces organiques utilisant un tel composé
WO2009125721A1 (fr) * 2008-04-10 2009-10-15 出光興産株式会社 Composé chimique utilisé pour un transistor organique en couches minces et transistor organique en couches minces
JP2012520872A (ja) * 2009-03-20 2012-09-10 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 新規有機電界発光化合物およびこれを使用する有機電界発光素子

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TWI477579B (zh) * 2010-02-12 2015-03-21 Nippon Steel & Sumikin Chem Co Organic electroluminescent elements
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KR101918851B1 (ko) * 2017-06-22 2018-11-14 중앙대학교 산학협력단 반도체 특성을 갖는 전도성 고분자 박막의 제조방법 및 반도체 특성을 갖는 전도성 고분자 박막을 포함하는 박막 트랜지스터

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WO2009125721A1 (fr) * 2008-04-10 2009-10-15 出光興産株式会社 Composé chimique utilisé pour un transistor organique en couches minces et transistor organique en couches minces
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