WO2006064896A1 - Materiau conducteur, composition pour le materiau conducteur, couche conductrice et dispositif et equipement electroniques - Google Patents

Materiau conducteur, composition pour le materiau conducteur, couche conductrice et dispositif et equipement electroniques Download PDF

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WO2006064896A1
WO2006064896A1 PCT/JP2005/023102 JP2005023102W WO2006064896A1 WO 2006064896 A1 WO2006064896 A1 WO 2006064896A1 JP 2005023102 W JP2005023102 W JP 2005023102W WO 2006064896 A1 WO2006064896 A1 WO 2006064896A1
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conductive material
layer
group
organic
compound
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Harunobu Komatsu
Yuji Shinohara
Koichi Terao
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Seiko Epson Corp
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Seiko Epson Corp
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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
    • C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
    • C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C08G64/1641—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
    • C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
    • C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C08G64/165—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
    • C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
    • C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C08G64/1683—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing other elements
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H10K85/6565—Oxadiazole compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • CONDUCTIVE MATERIAL COMPOSITION FOR THE CONDUCTIVE MATERIAL, CONDUCTIVE LAYER, ELECTRONIC DEVICE, AND ELECTRONIC EQUIPMENT
  • the present invention relates to a conductive material, a composition for the conductive material, a conductive layer, an electronic device, and electronic equipment, and more specifically to a conductive material, a composition for the conductive material from which a conductive layer having a high carrier transport ability can be made, a conductive layer formed using the conductive material as a main material, an electronic device provided with the conductive layer and having high reliability, and electronic equipment provided with the electronic device.
  • Electroluminescent devices using organic materials have been extensively developed in expectation of their use as solid-state luminescent devices or emitting devices for use in inexpensive large full-color displays.
  • organic EL device has a structure in which a light emitting layer is provided between a cathode and an anode. When an electric field is appliedbetween the cathode and the anode, electrons are injected into the light emitting layer from the cathode side, and holes are injected into the light emitting layer from the anode side.
  • the injected electrons and holes are recombined in the light emitting layer, which then causes their energy level to return from the conduction band to the valence band. At this time, excitation energy is released as light energy so that the light emitting layer emits light.
  • organic layers having different carrier transport properties from eachother (hereinafter, these layers are collectively referred to as "organic layers") on the electrode.
  • organic layers organic layers having different carrier transport properties from eachother
  • JP-A No. 2000-208254 Another method for improving the solvent resistance of a lower organic layer is found in JP-A No. 2000-208254.
  • This publication discloses a method in which a curing resin is added to an organic material constituting the lower organic layer to cure the organic material together with the curing resin.
  • the present invention is directedto a conductivematerialwhich is obtained by polycondensation reaction of substituents X 1 of compounds each represented by the following general formula (Al) through phosgene and/or its derivative to link the compounds:
  • R 1 S may be the same or different and each independently represents a straight-chain alkyl group having 2 to 8 carbon atoms
  • four R 2 S may be the same or different and each independently represents a hydrogen atom, a methyl group or an ethyl group
  • Y represents a group containing at least one substituted or unsubstituted aromatic hydrocarbon ring or substituted or unsubstituted heterocycle
  • two X 1 S may be the same or different and each independently represents a substituent represented by the following general formula (A2) :
  • n 1 is an integer of 2 to 8
  • the group Y contains at least one substituted or unsubstituted aromatic hydrocarbon ring.
  • the phosgene derivative is a compound represented by the following general formula (A3) :
  • Z 1 S may be the same or different and each independently represents an alkyl group, a phenyl group or a benzyl group each having 1 to 6 carbon atoms.
  • the two substituents X 1 are identical with each other.
  • the main skeletons mean portions of the compounds other than their substituents X 1 .
  • each substituent X 1 is bonded to the 3-, 4- or 5-position of the benzene ring.
  • the two substituents R 1 are identical with each other.
  • each substituent R 1 is bonded to the 4-position of the benzene ring.
  • the group Y consists of carbon atoms and hydrogen atoms.
  • the conductive material makes it possible for the conductive material to have a high hole transport ability, and therefore the resultant conductive layer to be formed of the conductive material can also have a high hole transport ability.
  • the group Y contains 6 to 30 carbon atoms in total.
  • the group Y contains 1 to 5 aromatic hydrocarbon rings.
  • the group Y is a biphenylene group or a derivative thereof.
  • the group Y contains at least one substitutedor unsubstitutedheterocycle.
  • the phosgene derivative is a compoundrepresentedby the following general formula (A3) :
  • Z 1 S may be the same or different and each independently represents an alkyl group, a phenyl group or a benzyl group each having 1 to 6 carbon atoms.
  • the two substituents X 1 are identical with each other.
  • each substituent X 1 is bonded to the 3-, 4- or 5-position of the benzene ring.
  • the two substituents R 1 are identical with each other.
  • each substituent R 1 is bonded to the 4-position of the benzene ring.
  • the heterocycle contains at least one heteroatom selectedfromthe group comprisingnitrogen, oxygen, sulfur, selenium and tellurium.
  • the heterocycle may be either of an aromatic heterocycle or a nonaromatic heterocycle, but the aromatic heterocycle is more preferable.
  • the group Y contains 1 to 5 heterocycles.
  • the group Y By allowing the group Y to have such a number of heterocyclic rings, it is possible to change the energy level of the valence and conduction bands or the size of the band gap of the conductive material sufficiently.
  • the group Y contains at least one substituted or unsubstituted aromatic hydrocarbon ring in addition to the heterocycle.
  • the group Y contains two aromatic hydrocarbon rings respectively bonded to each N in the general formula (Al) directly and at least one heterocycle existing between these aromatic hydrocarbon rings.
  • the group Y contains 2 to 75 carbon atoms in total.
  • composition for the conductive material which contains a compound represented by the following general formula (Al) and a phosgene derivative:
  • R 1 S may be the same or different and each independently represents a straight-chain alkyl group having 2 to 8 carbon atoms
  • four R 2 S may be the same or different and each independently represents a hydrogen atom, a methyl group or an ethyl group
  • Y represents a group containing at least one substituted or unsubstituted aromatic hydrocarbon ring or substituted or unsubstituted heterocycle
  • two X 1 S may be the same or different and each independently represents a substituent represented by the following general formula (A2) :
  • n 1 is an integer of 2 to 8.
  • composition for the conductive material described above it is possible to produce a conductive layer (polymer) having a high carrier transport ability.
  • a conductive layer mainly formed of the conductive material described above.
  • Such a conductive layer can have a high hole transport ability.
  • the conductive layer is used for a hole transport layer.
  • a hole transport layer can also have a high hole transport ability.
  • the average thickness of the hole transport layer is in the range of 10 to 150 nm.
  • the average thickness of the hole transport layer is in the range of 10 to 150 nm.
  • the conductive layer of the present invention described above may be used for an electron transport layer.
  • Such an electron transport layer can also have a high electron transport ability.
  • the average thickness of the electron transport layer is in the range of 10 to 100 nm.
  • the average thickness of the electron transport layer is in the range of 10 to 100 nm.
  • the conductive layer of the present invention described above may be used for an organic semiconductor layer.
  • Such an organic semiconductor layer can exhibit excellent semiconductor characteristics.
  • the average thickness of the organic semiconductor layer is in the range of 0.1 to 1,000 nm.
  • the average thickness of the organic semiconductor layer is in the range of 0.1 to 1,000 nm.
  • the other aspect of the present invention is directed to an electronic device comprising a laminated bodywhich includes the conductive layer as described above.
  • Such an electronic device can have high reliability.
  • Examples of the electronic device may include a light emitting device and a photoelectric transducer. These light emitting device and photoelectric transducer can also have high reliability.
  • the light emitting device includes an organic EL device.
  • Such an organic EL device can also have high reliability.
  • examples of the electronic device may also include a switching element.
  • a switching element can also have high reliability.
  • the switching element includes an organic thin film transistor.
  • Such an organic thin film transistor can also have high reliability.
  • Yet other aspect of the present invention is directed to electronic equipment comprising the electronic device described above.
  • Such electronic equipment can also have high reliability.
  • FIG. 1 is a cross-sectional view which shows an example of an organic EL device
  • FIG. 2(a) is a cross-sectional view of an organic TFT
  • FIG. 2(b) is a plan view of the organic TFT
  • FIG. 3(a) to FIG. 3(d) are illustrations which explain the manufacturing method of the organic TFT shown in FIG. 2;
  • FIG. 4(a) to FIG. 4(d) are illustrations which explain the manufacturing method of the organic TFT shown in FIG. 2;
  • FIG. 5 is a perspective view which shows the structure of a personal mobile computer (or a personal notebook computer) to which the electronic equipment according to the present invention is applied;
  • FIG. 6 is a perspective view which shows the structure of a mobile phone (including the personal handyphone system (PHS)) to which the electronic equipment according to the present invention is applied; and
  • PHS personal handyphone system
  • FIG. 7 is a perspective view which shows the structure of a digital still camera to which the electronic equipment according to the present invention is applied.
  • a conductive material according to the present invention contains as its main ingredient a polymer obtained by polycondensation reaction of substituents X 1 of compounds (which are an arylamine derivative) each represented by the following general formula (Al) through phosgene or its derivative to link or bond the compounds.
  • R 1 S may be the same or different and each independently represents a straight-chain alkyl group having 2 to 8 carbon atoms; four R 2 S may be the same or different and each independently represents a hydrogen atom, a methyl group, or an ethyl group; two X 1 S may be the same or different and each independently represents a substituent represented by the following general formula (A2); and Y represents a group containing at least one substituted or unsubstituted aromatic ring hydrocarbon or a group containing at least one substituted or unsubstituted heterocycle.
  • n 1 is an integer of 2 to 8.
  • the conductive material according to the present invention contains as its main gradient a polymer obtainedby linkingmain skeletons (arylamine skeletons) of the compounds each represented by the above-mentioned general formula (Al) via a chemical structure produced by polycondensation reaction of their substituents X 1 and phosgene representedbythe chemical formula COCl 2 and/or its derivative.
  • the main skeleton is a portion of each compound other than its substituents X 1
  • the chemical structure is represented by the following chemical formula (A4) (hereinafter, this chemical structure will be simply referred to as "link structure" on occasions).
  • n x s may be the same or different and each independently represents an integer of 2 to 8.
  • Such a polymer has a structure in which the main skeletons are repeatedly linked via the link structure represented by the general formula (A4), that is, a chemical structure in which two straight-chain carbon-carbon bonds (alkylene group) are bonded by a carbonate bond. Due to the chemical structure, the main skeletons repeatedly exist at a predetermined interval. Therefore, the interaction between the adjacent main skeletons can be decreased.
  • A4 the link structure represented by the general formula (A4)
  • Each main skeleton has a conjugated chemical structure, and a unique spread of the electron cloud thereof contributes to smooth transportation of carriers (holes or electrons) in the polymer.
  • the polymer exhibits a high carrier transport ability. Therefore, a conductive layer formed of such a polymer as its main material also has a high carrier transport ability.
  • substituent X 1 that is, the substituent X 1 represented by the general formula (A2)
  • phosgene and its derivative those such as follows are preferably selected.
  • the substituent X 1 has a straight-chain carbon-carbon link (i.e. , an alkylene group) in which n 1 is 2 to 8, in particular 3 to 6.
  • n 1 is 2 to 8, in particular 3 to 6.
  • each of the two substituents X 1 contains substantially the same number of carbon atoms, more preferably the same number of carbon atoms. This makes it possible for the adjacent main skeletons to exist at an interval of a certain distance. As a result, it is possible to prevent the electron density in the polymer from being biased. This makes it possible to improve the carrier transport ability of the polymer.
  • each substituent X 1 may be bonded to the 2- , 3-, 4-, 5- or 6-position of the benzene ring, but preferably bonded to the 3-, 4- or 5-position. This makes it possible to exhibit the effect obtained by linking the adjacent main skeletons via the link structure conspicuously. Namely, it is possible for the adjacent main skeletons to exist at a suitable interval more reliably.
  • Phosgene and/or its derivative is not limited to a specific one so long as it is possible to form the chemical structure represented by the general formula (A4) by the polycondensation reaction with the substituents X 1 (hydrated alkyl group) , but it is preferred to use one containing as its main ingredient phosgene and/or a compound represented by the following general formula (A3) (hereinafter, simply referred to as "compound (A3)" on occasions).
  • two Z 1 S may be the same or different and each independently represents an alkyl group, a phenyl group or a benzyl group each having 1 to 6 carbon atoms.
  • the link structure represented by the general formula (A4) has a structure having many conjugated ⁇ bonds such as a benzene ring, interaction occurs between the adjacent main skeletons through such a structure, which cancels the effect obtained by allowing the adjacent main skeletons to exist at a suitable interval.
  • each substituent R 1 has a straight-chain alkyl group having 2 to 8 carbon atoms, preferably a straight-chain alkyl group having 3 to 6 carbon atoms.
  • the two substituents R 1 contain substantially the same number of carbon atoms, more preferably the same number of carbon atoms. This makes it possible for the adjacent polymers to exist at an interval of a certain distance in the conductive layer. As a result, the density of the polymers in the conductive layer becomes uniform.
  • each substituent R 1 may be bonded to any of the 2- to 6-position of a benzene ring, but preferably it is bonded to the 4-position. This makes it possible to exhibit the effect of introduction of the substituents R 1 more conspicuously. Namely, it is possible to prevent reliably the adjacent polymers from closely approaching to each other.
  • the substituent R 2 is a hydrogen atom, a methyl group, or an ethyl group, and the substituent R 2 is selected in accordance with the number of carbon in the substituent R 1 . Specifically, when the number of carbon in the substituent R 1 is large, a hydrogen atom is selected as the substituent R 2 , while when the number of carbon in the substituent R 1 is small, a methyl group or an ethyl group is selected as the substituent R 2 .
  • the group Y contains at least one substituted or unsubstituted aromatic hydrocarbon ring or at least one substituted or unsubstituted heterocyclic ring.
  • the group Y has 6 to 30 carbon atoms, more preferably 10 to 25 carbon atoms, and even more Dreferablv 10 to 20 carbon atoms, in total. Further, in the group Y, it is preferred that the number of aromatic hydrocarbon ring is 1 to 5, more preferably 2 to 5, and even more preferably 2 to 3.
  • the hole transport ability of the resultant polymer becomes excellent, and thus the resultant conductive layer can also have an excellent hole transport ability.
  • such a heterocyclic ring contains at least one heteroatom selected from among nitrogen, oxygen, sulfur, selenium, and tellurium.
  • the heterocyclic ring may be either an aromatic heterocycle or a nonaromatic heterocycle, but an aromatic heterocycle is preferably used.
  • an aromatic heterocycle it is possible to prevent appropriately the electron density of themain skeletonwith a conjugated chemical structure from being biased, that is, it is possible to prevent localization of ⁇ electrons appropriately. As a result, the carrier transport ability of the polymer is prevented frombeing impaired.
  • the group Y contains 1 to 5 heterocyclic rings, more preferably 1 to 3 heterocyclic rings.
  • the group Y By allowing the group Y to have such a number of heterocyclic rings, it is possible to change the energy level of the valence and conduction bands or the size of the band gap of the polymer sufficiently.
  • the group Y may further contain at least one aromatic hydrocarbon ring in addition to the at least one heterocyclic ring.
  • the group Y contains two aromatic hydrocarbon rings each bonded to each N in the general formula (Al) directly and at least one heterocyclic ring which exists between these aromatichydrocarbonrings. Byusing suchagroup Y, it is possible to prevent the electron density of the polymer from being biased reliably. As a result, the polymer can have an even (uniform) carrier transport ability.
  • the group Y has 2 to 75 carbon atoms, more preferably 2 to 50 carbon atoms, in total. If the group Y has too many carbon atoms in total, the solubility of the compound represented by the general formula (Al) in a solvent tends to be lowered depending on the kind of its substituent X 1 , creating a possibility that the range of the choices of solvents to be used in preparing the composition for conductive materials according to the present invention becomes narrow.
  • each Q 1 may be the same or different and each independently represent N-T 1 , S, O, Se, or Te (where T 1 represents H, CH 3 , or Ph)
  • each Q 2 may be the same or different and each independently represent S or O
  • each Q 3 may be the same or different and each independently represent N-T 3 , S, O, Se, or Te (where T 3 represents H, CH 3 , C 2 H 5 or Ph) .
  • a polymer obtained by selecting any one of the chemical formulas (D2), (D16), (D18) and (D20) as the group Y can exhibit a high hole transport ability as compared to a polymer obtained by selecting the chemical formula (D17) and can exhibit an especially high hole transport ability as compared to a polymer obtained by selecting the chemical formula (D8) or (D19).
  • a polymer obtained by selecting any one of the chemical formulas (D8), (D17) and (D19) as the group Y can exhibit a high electron transport ability as compared to a polymer obtained by the chemical formula (D2) or (D16). Further, the polymer obtained by selecting any one of the chemical formulas (D8) , (D17) and (D19) as the group Y can also exhibit an especially high electron transport ability as compared to a polymer obtainedby selecting the chemical formula (D18) or (D20).
  • the unsubstituted heterocyclic ring and/or the unsubstituted aromatic hydrocarbon ring contained in the group Y may introduce a substituent so long as the planarity of the main skeleton is not greatly affected.
  • a substituent include an alkyl group having a relatively small number of carbon atoms such as a methyl group or an ethyl group or and a halogen group and the like.
  • the conductive layer since such a conductive material is mainly formed of a polymer obtained by the polycondensation reaction, the conductive layer also has excellent solvent resistance. As a result, in the case where an upper layer is formed onto the conductive layer in contact therewith, it is possible toprevent assuredly the conductive layer from being swelled up or dissolved by the solvent or dispersant contained in a material for forming the upper layer.
  • the electronic device of the present invention is embodied as an organic electroluminescent device (hereinafter, simply referred to as an "organic EL device”) that is a light emitting device.
  • organic EL device organic electroluminescent device
  • FIG. 1 is a cross-sectional view which shows an example of the organic EL device.
  • the organic EL device 1 shown in FIG. 1 includes a transparent substrate 2, an anode 3 provided on the substrate 2, an organic EL layer 4 provided on the anode 3, a cathode 5 provided on the organic EL layer 4 and a protection layer 6 provided so as to cover these layers 3, 4 and 5.
  • the substrate 2 serves as a support for the organic EL device 1, and the layers described above are formed on the substrate 2.
  • a material having a light-transmitting property and a good optical property can be used as a constituent material of the substrate 2.
  • Such a material examples include various resins such as polyethylene terephthalate, polyethylene naphthalate, polypropylene, cycloolefin polymer, polyamide, polyethersulfone, polymethylmethacrylate, polycarbonate, and polyarylate, and various glass materials, and the like. At least one of these materials can be used as a constituent material of the substrate 2.
  • the thickness of the substrate 2 is not particularly limited, but is preferably in the range of about 0.1 to 30 mm, more preferably in the range of about 0.1 to 10 mm.
  • the anode 3 is an electrode which injects holes into the organic EL layer 4 (that is, into a hole transport layer 41 described later) .
  • This anode 3 is made substantially transparent (which includes transparent and colorless, colored and transparent, or translucent) so that light emission from the organic EL layer 4 (that is, from a light emitting layer 42 described later) can be visually identified.
  • anode material a material having a high work function, excellent conductivity, and a light transmitting property is preferably used as the constituent material of the anode 3 (hereinafter, referred to as "anode material").
  • anode material examples include oxides such as ITO (Indium Tin Oxide), SnO 2 , Sb-containing SnO 2 , and Al-containing ZnO, Au, Pt, Ag, Cu, and alloys containing two or more of them. At least one of these materials can be used as an anode material.
  • the thickness of the anode 3 is not limited to any specific value, but is preferably in the range of about 10 to 200 nm, more preferably in the range of about 50 to 150 nm. If the thickness of the anode 3 is too thin, there is a case that a function of the anode 3 will not be sufficiently exhibited.
  • conductive resins such as polythiophene, polypyrrole, and the like can also be used as the anode material.
  • the cathode 5 is an electrode which injects electrons into the organic EL layer 4 (that is, into an electron transport layer 43 described later) .
  • cathode material As a constituent material of the cathode 5 (hereinafter, referred to as "cathode material” ) , amaterial having a lowwork function is preferably used.
  • cathode material examples include Li, Mg, Ca, Sr, La, Ce, Er, Eu, Sc, Y, Yb, Ag, Cu, Al, Cs, Rb, and alloys containing two or more of them. At least one of these materials can be used as a cathode material.
  • an alloy containing a stable metallic element such as Ag, Al, or Cu specifically an alloy such as MgAg, AlLi, or CuLi is preferablyused.
  • an alloy containing a stable metallic element such as Ag, Al, or Cu
  • an alloy such as MgAg, AlLi, or CuLi is preferablyused.
  • the use of such an alloy as a cathode material makes it possible to improve the electron injection efficiency and stability of the cathode 5.
  • the thickness of the cathode 5 is preferably in the range of about 1 nm to 1 ⁇ m, more preferably in the range of about 100 to 400 nm. If the thickness of the cathode 5 is too thin, there is a case that a function of the cathode 5 will not be sufficiently exhibited. On the other hand, if the cathode 5 is too thick, there is a case that the light emitting efficiency of the organic EL device 1 will be lowered.
  • the organic EL layer 4 is provided between the anode 3 and the cathode 5.
  • the organic EL layer 4 includes the hole transport layer 41, the light emitting layer 42, and the electron transport layer 43. These layers 41, 42 and 43 are formed on the anode 3 in this order.
  • the hole transport layer 41 has the function of transporting holes, which are injected from the anode 3, to the light emitting layer 42.
  • the electron transport layer 43 has the function of transporting electrons, which are injected from the cathode 5, to the light emitting layer 42.
  • the conductive material according to the present invention can be used as a constituent material for one of the hole transport layer 41 and the electron transport layer 43 or for both the layers 41, 43.
  • the conductive material according to the present invention can be used as the constituent material of the hole transport layer 41.
  • a compound having a chemical structure of the group Ywhich is constituted from a substituted or unsubstituted aromatic hydrocarbon ring can be used as the constituent material of the hole transport layer 41.
  • constituent material of the electron transport layer 43 are not limited to specific materials, and various materials can be used for the electron transport layer 43.
  • Examples of such materials that can be used for the electron transport layer 43 include: benzene-based compounds (starburst-based compounds) such as 1,3,5-tris[ (3-phenyl-6-tri-fluoromethyl)quinoxaline-2-yl] benzene (TPQl), and
  • TPQ2 1,3,5-tris[ ⁇ 3-(4-t-butylphenyl) -6-trisfluoromethyl ⁇ quinoxal ine-2-yl]benzene
  • naphthalene-based compounds such as naphthalene
  • phenanthrene-based compounds such as phenanthrene
  • chrysene-based compounds such as chrysene
  • perylene-based compounds such as perylene
  • anthracene-based compounds such as anthracene
  • pyrene-based compounds such as pyrene
  • acridine-based compounds such as acridine,- stilbene-based compounds such as stilbene
  • thiophene-based compounds such as BBOT
  • butadiene-based compounds such as butadiene
  • coumarin-based compounds such as coumarin
  • quinoline-based compounds such as quinoline
  • bistyryl-based compounds such as bistyryl
  • both of the hole transport layer 41 and the electron transport layer 43 are formed using the conductive material according to the present invention as a main material.
  • a constituent material of the hole transport layer 41 and a constituent material of the electron transport layer 43 are selected in consideration of their hole transport ability and electron transport ability.
  • these constituent materials are selected so that the hole transport ability of the hole transport layer 41 becomes relativelyhigher than that of the electron transport layer 43 and the electron transport ability of the hole transport layer 41 becomes relatively lower than that of the electron transport layer 43.
  • these constituent materials are selected so that the electron transport ability of the electron transport layer 43 becomes relatively higher than that of the hole transport layer 41 and the hole transport ability of the electron transport layer 43 becomes relatively lower than that of the hole transport layer 41.
  • a conductive material for forming an electron transport layer 43 is preferably a polymer of a compound represented by the general formula (1) in which the group Y has a chemical structure represented by the chemical formula (D7) or (D19).
  • a polymer of a compound represented by the general formula (1) in which the group Y has a chemical structure represented by the chemical formula (D17) may also be used as a conductive material for forming the electron transport layer 43.
  • the conductive material for forming the hole transport layer 41 may also be a polymer of a compound represented by the general formula (1) in which the group Y has a chemical structure represented by the chemical formula (D2) or (D16).
  • the volume resistivity of the hole transport layer 41 is preferably 10 ⁇ -cm or larger, more preferably 10 2 ⁇ -cm or larger. This makes it possible to provide an organic EL device 1 having a higher light emitting efficiency.
  • the thickness of thehole transport layer 41 is not limited to any specific value, but is preferably in the range of about 10 to 150 nm, more preferably in the range of about 50 to 100 nm. If the thickness of the hole transport layer 41 is too thin, there is a case that a pin hole may be produced. On the other hand, if the thickness of the hole transport layer 41 is too thick, there is a case that the transmittance of the hole transport layer 41 may be lowered so that the chromaticity (hue) of luminescent color of the organic EL device 1 is changed.
  • the thickness of the electron transport layer 43 is not limited to any specific value, but is preferably in the range of about 1 to 100 nm, more preferably in the range of about 20 to 50 nm. If the thickness of the electron transport layer 43 is too thin, there is a case that a pin hole may be produced, thereby causing a short-circuit. On the other hand, if the electron transport layer 43 is too thick, there is a case that the value of resistance may become high.
  • the conductivematerial according to the present invention is particularly useful for forming a relatively thin hole transport layer 41 or electron transport layer 43.
  • any material can be used as a constituent material of the light emitting layer 42 (hereinafter, referred to as "light emittingmaterial” ) so long as it can provide a fieldwhere holes can be injected from the anode 3 and electrons can be injected from the cathode 5 during the application of a voltage to allow the holes and the electrons to be recombined.
  • Such light emitting materials include various low-molecular light emitting materials and various high-molecular light emitting materials (which will be mentioned below) • At least one of these materials can be used as a light emitting material.
  • a low-molecular light emitting material makes it possible to obtain a dense light emitting layer 42, thereby improving the light emitting efficiency of the light emitting layer 42.
  • a high-molecular light emitting material is relatively easily dissolved in a solvent, the use of such a high-molecular light emitting material makes it easy to form a light emitting layer 42 by means of various application methods such as an ink-jet method and the like.
  • the low-molecular light emitting material and the high-molecular light emitting material are used together, it is possible to obtain the synergistic effect resulting from the effect of the low-molecular light emitting material and the effect of the high-molecular light emittingmaterial. That is, it is possible to obtain the effect that a dense light emitting layer 42 having excellent light emitting efficiency can be easily formed by means of various application methods such as the ink-jet method and the like.
  • Examples of such a low-molecular light emitting material include: benzene-based compounds such as distyrylbenzene (DSB) , and diaminodistyrylbenzene (DADSB) ; naphthalene-based compounds such as naphthalene and Nile red; phenanthrene-based compounds such as phenanthrene; chrysene-based compounds such as chrysene and 6-nitrochrysene; perylene-based compounds such as perylene and
  • benzene-based compounds such as distyrylbenzene (DSB) , and diaminodistyrylbenzene (DADSB)
  • naphthalene-based compounds such as naphthalene and Nile red
  • phenanthrene-based compounds such as phenanthrene
  • chrysene-based compounds such as chrysene and 6-nitrochrysene
  • perylene-based compounds such as perylene
  • N,N' -bis(2, 5-di-t-butylphenyl)-3,4,9,10-perylene-di-carboxy imide BPPC
  • coronene-based compounds such as coronene
  • anthracene-based compounds such as anthracene and bisstyrylanthracene
  • pyr ⁇ ne-based compounds such as pyrene
  • pyran-based compounds such as 4-(di-cyanomethylene) -2-methyl-6-(para-dimethylaminostyryl) -4H-pyran (DCM);
  • acridine-based compounds such as acridine
  • stilbene-based compounds such as stilbene
  • thiophene-based compounds such as 2, 5-dibenzooxazolethiophene
  • benzooxazole-based compounds such as benzooxazole
  • benzoimidazole-based compounds such as benzoimidazole
  • benzothiazole-based compounds such
  • Examples of a high-molecular light emitting material include polyacetylene-based compounds such as trans-type polyacetylene, cis-type polyacetylene, poly(di-phenylacetylene) (PDPA), and poly(alkyl, phenylacetylene) (PAPA); polyparaphenylenevinylene-based compounds such as poly(para-phenylenevinylene) (PPV), poly(2,5-dialkoxy-para-phenylenevinylene) (RO-PPV) , cyano-substituted-poly(para-phenylenevinylene) (CN-PPV) , poly(2-dimethyloctylsilyl-para-phenylenevinylene) (DMOS-PPV), and poly(2-methoxy-5-(2' -ethylhexoxy)-para-phenylenevinylene)_ (MEH-PPV) ; polythiophene-based compounds such as poly(3-alkylthi
  • poly(thiophene/styrenesulfonic acid) such as poly(3,4-ethylenedioxythiophene/styrenesulfonic acid) or an arylamine compound such as
  • N,N' -bis(l-naphthyl)-N,N' -diphenyl-benzidine( ⁇ -NPD) is used as a constituent material of the hole transport layer 41 and a triazole-based compound such as 3,4,5-triphenyl-l,2,4-triazole or an oxadiazole compound such as 2-(4-t-butylphenyl)-5-(biphenyl-4-yl) -1,3,5-oxadiazole (PBD) is used as a constituent material of the electron transport layer 43, a polymer of the compound represented by the general formula (1) in which the group Y has a chemical structure represented by the chemical formula (D12) or (D14) can be used as a conductive material for forming a light emitting layer 42.
  • a triazole-based compound such as 3,4,5-triphenyl-l,2,4-triazole or an oxadiazole compound such as 2-(4-t-butylphenyl)
  • the thickness of the light emitting layer 42 is not limited to any specific value, but is preferably in the range of about 10 to 150 nm, more preferably in the range of about 50 to 100 nm. By setting the thickness of the light emitting layer to a value within the above range, recombination of holes and electrons efficiently occurs, thereby enabling the light emitting efficiency of the light emitting layer 42 to be further improved. It is to be noted here that any one of the electron transport layer 41, the light emitting layer 42, and the electron transport layer 43 in the organic EL device 1 may be formed using the conductive material according to the present invention or all the layers 41, 42, and 43 may be formed using the conductive material according to the present invention.
  • each of the light emitting layer 42, the hole transport layer 41, and the electron transport layer 43 is separately provided, they may be formed into a hole-transportable light emitting layer which combines the hole transport layer 41 with the light emitting layer 42 or an electron-transportable light emitting layer which combines the electron transport layer 43 with the light emitting layer 42.
  • an area in the vicinity of the boundary between the hole-transportable light emitting layer and the electron transport layer 43 or an area in the vicinity of the boundary between the electron-transportable light emitting layer and the hole transport layer 41 functions as the light emitting layer 42.
  • holes injected from an anode into the hole-transportable light emitting layer are trapped by the electron transport layer
  • electrons injected from a cathode into the electron-transportable light emitting layer are trapped in the electron-transportable light emitting layer.
  • any additional layer may be provided according to its purpose.
  • a hole injecting layer for improving the injection efficiency of holes from the anode 3 may be providedbetween the hole transport layer 41 and the anode 3, or an electron injecting layer for improving the injection efficiency of electrons from the cathode 5 may be provided between the electron transport layer 43 and the cathode 5.
  • the conductive material according to the present invention can be used as a constituent material of the hole injecting layer and/or the electron injecting layer.
  • a constituent material of a hole injecting layer other than the conductive material according to the present invention for example, copper phthalocyanine, 4,4' ,4' ' -tris(N,N-phenyl-3-methylphenylamino)triphenylamine (M-MTDATA), or the like can be used.
  • M-MTDATA 4,4' ,4' ' -tris(N,N-phenyl-3-methylphenylamino)triphenylamine
  • the protection layer 6 is provided so as to cover the layers 3, 4 and 5 constituting the organic EL device 1.
  • This protection layer 6 has the function of hermetically sealing the layers 3, 4 and 5 constituting the organic EL device 1 to shut off oxygen and moisture.
  • Examples of a constituent material of the protection layer 6 include Al, Au, Cr, Nb, Ta and Ti, alloys containing them, silicon oxide, various resin materials, and the like.
  • a conductive material is used as a constituent material of the protection layer 6, it is preferred that an insulating film is provided between the protection layer 6 and each of the layers 3, 4 and 5 to prevent a short circuit therebetween, if necessary.
  • the organic EL device 1 can be used for a display, for example, but it can also be used for various optical purposes such as a light source and the like.
  • the drive system thereof is not particularly limited, and either of an active matrix system or a passive matrix system may be employed.
  • the organic EL device 1 as described above can be manufactured in the following manner, for example.
  • a substrate 2 is prepared, and then an anode 3 is formed on the substrate 2.
  • the anode 3 can be formed by, for example, chemical vapor deposition (CVD) such as plasma CVD, thermal CVD, and laser CVD, vacuum deposition, sputtering, dry plating such as ion plating, wet plating such as electrolytic plating, immersion plating, and electroless plating, thermal spraying, a sol-gel method, a MOD method, bonding of a metallic foil, or the like.
  • CVD chemical vapor deposition
  • thermal CVD thermal CVD
  • laser CVD vacuum deposition
  • vacuum deposition sputtering
  • dry plating such as ion plating
  • wet plating such as electrolytic plating, immersion plating, and electroless plating
  • thermal spraying a sol-gel method, a MOD method, bonding of a metallic foil, or the like.
  • the method for forming the hole transport layer 41 various methods can be employed if the methods allow the substituents X 1 of the compounds each represented by the above-mentioned general formula (Al) (hereinafter, simply referred to as "the compound (Al)” on occasions) to make polycondensation reaction with phosgene and/or its derivative.
  • various application methods such as a spin coating method, a casting method, a micro gravure coating method, a gravure coating method, a bar coating method, a roll coating method, awire-bar coatingmethod, a dip coating method, a spray coating method, a screen printing method, a flexographic printing method, an offset printing method, an ink-jet method, and the like can be employed.
  • a spin coating method a casting method, a micro gravure coating method, a gravure coating method, a bar coating method, a roll coating method, awire-bar coatingmethod, a dip coating method, a spray coating method, a screen printing method, a flexographic printing method, an offset printing method, an ink-jet method, and the like
  • a spin coating method a casting method
  • a micro gravure coating method e.g., a gravure coating method
  • bar coating method e.g., a bar coating method
  • a roll coating method e.g., a roll coating method
  • organic solvent examples include halogen compound-based solvents such as dichloromethane (methylene chloride), trichloromethane, carbon tetrachloride, 1,1-dichloroethane, 1,2-dichloroethane,
  • halogen compound-based solvents such as dichloromethane (methylene chloride), trichloromethane, carbon tetrachloride, 1,1-dichloroethane, 1,2-dichloroethane,
  • 1, 1,1-trichloroethane, and pentachloroethane aromatic hydrocarbon-based solvents such as toluene, xylene, and benzene; ether-based solvents such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane (DME), 1,4-dioxane, tetrahydrofuran (THF), tetrahydropyran (THP), anisole, diethylen glycol dimethyl ether, and diethylen glycol ethyl ether.
  • DME 1,2-dimethoxyethane
  • THF tetrahydrofuran
  • TTP tetrahydropyran
  • anisole diethylen glycol dimethyl ether
  • diethylen glycol ethyl ether diethylen glycol ethyl ether.
  • the base is used for stabilizing a ⁇ arbonyl group supplied from phosgene.
  • the base include basic organic solvents such as pyridine, triethylamine, tributhylamine, dimethyl aniline, formyldimethylamine, and triphenylamine; alkali metal hydroxide such as potassium hydroxide, lithium hydroxide, and cesium hydroxide.
  • basic organic solvents such as pyridine, triethylamine, tributhylamine, dimethyl aniline, formyldimethylamine, and triphenylamine
  • alkali metal hydroxide such as potassium hydroxide, lithium hydroxide, and cesium hydroxide.
  • one containing the basic organic solvent as its major component is preferably used.
  • the basic organic solvent can be eliminated or removed from the obtained hole transport layer 41 relatively easily. Therefore, it is possible to prevent reliably the basic organic solvent from remaining in the hole transport layer 41 as impurities.
  • pyridine, triethylamine, tributhylamine, and dimethyl aniline are preferably used because they function as a catalyst for promoting the polycondensation reaction between the substituents X 1 and phosgene in the next step (A2-Ib) . This makes it possible to promote the polycondensation reaction more effectively.
  • examples of the catalyst further include in addition to the above substances quaternary ammonium salts such as trimethyl benzyl ammonium chloride, triethyl benzyl ammonium chloride, and tributhyl benzyl ammonium chloride, and they may be contained in the hole transport material.
  • the mixing ratio of the organic solvent and the base is preferably in the range of 10:1 to 2:1 in volume ratio, and more preferably in the range of 5:1 to 3:1.
  • the temperature of the mixture upon promoting the polycondensation reaction is preferably in the range of -20 to 20°C, and more preferably in the range of -20 to 0 0 C.
  • reaction time is preferably in the range of 1 minute to 4 hours, and more preferably in the range of 15 minutes to 2 hours, though this is slightly changed depending on the temperature of the mixture.
  • the thus obtained hole transport layer 41 maybe subjected to aheat treatment, as needed, in an atmosphere or an inert atmosphere or under reduced pressure (in a vacuum) . In this way, it is possible to dry (eliminate the solvent or dispersion medium) or solidify the hole transport layer 41, for example. In this regard, it is to be noted that the hole transport layer 41 may be dried without such a heat treatment.
  • phosgene is preferably used for the reaction with the compound (Al), but triphosgene, bromphosgene, bis(2,4,6-trichlorophenyl) carbonate, bis(2,4-dichlorophenyl) carbonate, bis(2-cyanophenyl) carbonate, chloroformate trichloromethyl, and the like may be used other than phosgene. They can be used singly or in combination with two or more of them.
  • composition for the conductive material according to the present invention (a hole transport material) containing the compound (Al) and the phosgene derivative described above is applied (or supplied) onto the anode 3.
  • the organic solvents described above with reference to the step ⁇ A2-Ia ⁇ can be used.
  • examples of solvents that can be used in this ester exchangemethod other than the above-mentioned organic solvents include: inorganic solvents such as nitric acid, sulfuric acid, ammonia, hydrogen peroxide, water, carbon disulfide, carbon tetrachloride, and ethylene carbonate,- and various organic solvents such as ketone-based, solvents e.g.
  • methyl ethyl ketone MEK
  • MIBK methyl isobutyl ketone
  • MIPK methyl isopropyl ketone
  • alcohol-based solvents e.g. methanol, ethanol, isopropanol, ethylene glycol, diethylene glycol (DEG), and glycerin
  • cellosolve-based solvents e.g. methyl cellosolve, ethyl cellosolve, and phenyl cellosolve
  • aliphatic hydrocarbon-based solvents e.g.
  • aromatic heterocyclic compound-based solvents e-9- pyridine, pyrazine, furan, pyrrole, thiophene, and methyl pyrrolidone; amide-based solvents e.g. N,N-dimethylformamide (DMF) and N,N-dimethylacetamide (DMA); ester-based solvents e.g. ethyl acetate, methyl acetate, and ethyl formate; sulfur compound-based solvents e.g. dimethyl sulfoxide (DMSO) and sulfolane; nitrile-based solvents e.g.
  • DMF N,N-dimethylformamide
  • DMA N,N-dimethylacetamide
  • ester-based solvents e.g. ethyl acetate, methyl acetate, and ethyl formate
  • sulfur compound-based solvents e.g. dimethyl sulfoxide (DMSO) and
  • acetonitrile e.g. formic acid, acetic acid, trichloroacetic acid, and trifluoroacetic acid; and mixed solvents containing them.
  • organic acid-based solvents e.g. formic acid, acetic acid, trichloroacetic acid, and trifluoroacetic acid; and mixed solvents containing them.
  • the mixing ratio of the compound (Al) and the phosgene derivative in the composition for the conductive material is preferably in the range of 1:1 to 1:12 in a molar ratio, and more preferably in the range of 1:2 to 1:6. This makes it possible to promote the polycondensation reaction between the substituents X 1 and the phosgene derivative effectively, and to thereby prevent effectively the compound (Al) from remaining unreacted in the obtained hole transport layer 41. Further, by containing the phosgene derivative of which amount is larger than the compound (Al) as the mixing ratio mentioned above, it is possible for the phosgene derivative to exhibit a function of a reaction solvent.
  • a catalyst for promoting the ester exchange reaction may be added to the composition for the conductive material.
  • catalysts same as those mentioned above with reference to the step (A2-Ia) may be used.
  • the ester exchange reaction (polycondensation reaction) between the substituents X 1 and the phosgene derivative is progressed, and therefore it is possible to obtain a polymer (that is, the conductive material of the present invention) which is linked by the link structure. Further, it is also possible to eliminate the by-product and the unreacted phosgene derivative from the hole transport layer 41 reliably. As a result, the hole transport layer 41 which is mainly formed of the conductive material of the present invention is formed on the anode 3.
  • the temperature for heating the composition for the conductive material is preferably in the range of 120 to 200 0 C, andmore preferably in the range of 150 to 180°C. If the heating temperature is lower than the above-mentioned lower limit value, there is a case that formation of polymer does not progress adequately depending on the kind of the phosgene derivative used. On the other hand, if the heating temperature is higher than the above-mentioned upper limit value, there is a possibility that aresultant polymerwill be degraded or deteriorated, which is undesirable. However, by setting the heating temperature within the above-mentioned range, it is possible to eliminate the by-product and the unreacted phosgene derivative from the obtained hole transport layer 41 assuredly.
  • reaction time is preferably in the range of 1 minute to 4 hours, and more preferably in the range of 15 minutes to 2 hours, though this is slightly changed depending on the temperature of the mixture.
  • the heating of the composition for the conductive material is carried out under reduced pressure.
  • examples of the by-product represented by the chemical formula Z 1- -OH include methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, tert-butyl alcohol, b-amyl alcohol, isoamyl alcohol, sec-amyl alcohol, tert-amyl alcohol, sec-isoamyl alcohol, diethyl carbinol, tert-butyl carbinol, 1-hexanol, 2-hexanol, 3-hexanol, 2-methyl-2-pentanol, 2-methyl-3-pentanol, 3-methyl-1-pentanol, 3-methyl-2-pentanol,
  • the degree of the reduced pressure is preferably 10 5 Pa or less, and more preferably 10 3 Pa or less. This makes it possible to eliminate the by-product and the unreacted phosgene derivative from the hole transport layer 41 reliably.
  • the heating is carried out in an inert gas atmosphere such as nitrogen gas and rare gas e.g. argon gas, helium gas, xenon gas, or the like.
  • an inert gas atmosphere such as nitrogen gas and rare gas e.g. argon gas, helium gas, xenon gas, or the like.
  • the hole transport layer 41 By forming the hole transport layer 41 using the conductive material according to the present invention as its main material by means of the method described above, it is possible to prevent the hole transport layer 41 from being swelled up or dissolved by a solvent or a dispersion medium contained in a light emitting layer material when the light emitting layermaterial is supplied in the next step [3A] . With this result, it is possible to prevent mutual dissolution from occurring between the hole transport layer 41 and the light emitting layer 42 reliably.
  • the hole transport layer 41 using the conductive material (polymer) according to the present invention as its main material, it is possible to prevent reliably the constituent materials of the hole transport layer 41 and the light emitting layer 42 frombeing mixed to each other with the elapse of time at the boundary of these layers 41, 42 in the obtained organic EL device.
  • the weight average molecular weight of the polymer is not particularly limitedto any specificvalue, but it is preferably in the range of 2,000 to 1,000,000, and more preferably in the range of 5,000 to 300,000. This makes it possible to prevent reliably swelling-up andmutual dissolution of the polymer from occurring.
  • the hole transport layer 41 may contain the compound (Al) and the phosgene derivative to such an extent that occurrence of the mutual dissolution of the hole transport layer 41 and the light emitting layer 42 is prevented.
  • a light emitting layer 42 is formed on the hole transport layer 41.
  • the light emitting layer 42 can be formed by, for example, applying onto the hole transport layer 41, a light emitting layermaterial (that is, amaterial for forming a light emitting layer) obtained by dissolving the light emitting material as described above in a solvent or dispersing the light emitting material in a dispersion medium.
  • a light emitting layermaterial that is, amaterial for forming a light emitting layer
  • solvents or dispersion media in which the light emitting material is to be dissolved or dispersed the same solvents or dispersion media that have been mentioned with reference to the step of forming the hole transport layer [A2] can be used.
  • an electron transport layer 43 is formed on the light emitting layer 42.
  • the electron transport layer 43 can be formed using the composition for conductive materials according to the present invention in the same manner that has been described with reference to the step of forming the hole transport layer [A2].
  • the electron transport layer 43 can be formed using the known electron transport materials described above in the same manner that has been described with reference to the step of forming the light emitting layer [A3].
  • a solvent or dispersion medium in which the composition for conductive materials for use in forming the electron transport layer 43 is to be dissolved or dispersed is selected from among those which do not cause swelling and dissolution of the light emitting layer 42.
  • the cathode 5 can be formed by, for example, vacuum deposition, sputtering, bonding of ametallic foil, or the like.
  • a protection layer 6 is formed so as to cover the anode 3, the organic EL layer 4, and the cathode 5.
  • the protection layer 6 can be formed or provided by, for example, bonding a box-like protection cover made of the material as mentioned above by the use of various curable resins (adhesives) .
  • thermosetting resins As for such curable resins, all of thermosetting resins, photocurable resins, reactive curable resins, and anaerobic curable resins can be used.
  • the organic EL device 1 is manufactured through these steps as described above.
  • the electronic device of the present invention is embodied as an organic thin film transistor that is a switching element (hereinafter, simply referred to as an "organic TFT") .
  • FIG. 2(a) is a cross-sectional view of an organic TFT 10
  • FIG. 2(b) is a plan view of the organic TFT 10. It is to be noted that in the following description, the upper side and the lower side in FIG. 2(a) will be referred to as “upper side” and “lower side”, respectively.
  • the organic TFT 10 shown in FIG. 2 is provided on a substrate 20.
  • a source electrode 30, a drain electrode 40, an organic semiconductor layer (that is, a conductive layer according to the present invention) 50, a gate insulating layer 60, and a gate electrode 70 are laminated in this order from the side of the substrate 20.
  • the source electrode 30 and the drain electrode 40 are separately provided on the substrate 20, and the organic semiconductor layer 50 is provided so as to cover these electrodes 30 and 40.
  • the gate insulating layer 60 is provided on the organic semiconductor layer 50.
  • the gate electrode 70 is provided so as to overlap with at least a region between the source electrode 30 and the drain electrode 40.
  • the region in the organic semiconductor layer 50 which is existed between the source electrode 30 and the drain electrode 40 functions as a channel region 510 where carriers are moved.
  • channel length L the length of the channel region 510 in a direction that carriers are moved, that is, the distance between the source electrode 30 and the drain electrode 40
  • channel width W the length of the channel region 510 in a direction orthogonal to the direction of the channel length L.
  • the organic TFT 10 is an organic TFT having a structure in which the source electrode 30 and the drain electrode 40 are provided so as to be closer to the substrate 20 than the gate electrode 70 provided through the gate insulating layer 60. That is, the organic TFT 10 is an organic TFT having a top gate structure.
  • the substrate 20 supports the layers (or the components) constituting the organic TFT 10.
  • a substrate 20 for example, the same substrate that has been described with reference to the substrate 2 of the organic EL device 1 can be used.
  • a silicon substrate or a gallium arsenide substrate may be used as the substrate 20.
  • the source electrode 30 and the drain electrode 40 are provided side by side at a predetermined distance in the direction of the channel length L.
  • the constituent material of the source electrode 30 and the drain electrode 40 is not particularly limited so long as it has conductivity.
  • Examples of such a constituent material include metallic materials such as Pd, Pt, Au, W, Ta, Mo, Al, Cr, Ti, Cu, and alloys containing two ormore of them, conductive oxidematerials suchas ITO, FTO, ATO, and SnO 2 , carbonmaterials such as carbon black, carbon nanbtube, and fullerene, and conductive polymeric materials such as polyacetylene, polypyrrole, polythiophene e.g., PEDOT (poly-ethylenedioxythiophene) , polyaniline, poly(p-phenylene) , poly(p-phenylenevinylene) , polyfluorene, polycarbazole, polysilane, and derivatives thereof.
  • metallic materials such as Pd, Pt, Au, W, Ta, Mo, Al, Cr, Ti, Cu, and alloys containing two ormore of them
  • the conductive polymeric materials are usually dopedwith iron chloride, iodine, strong acid, organic acid, or a polymer such as polystyrenesulfonic acid so as to have conductivitywhen used. These conductive materials can be used singly or in combination of two or more of them.
  • each of the source electrode 30 and the drain electrode 40 is not particularly limited, but is preferably in the range of about 30 to 300 nm, more preferably in the range of about 50 to 200 nm.
  • the distance between the source electrode 30 and the drain electrode 40, that is, the channel length L is preferably in the range of about 2 to 30 ⁇ m, more preferably in the range of about 2 to 20 ⁇ m.
  • the channel width W is preferably in the range of about 0.1 to 5 mm, more preferably in the range of about 0.3 to 3 mm.
  • the organic semiconductor layer 50 is provided on the substrate 20 so as to cover the source electrode 30 and the drain electrode 40.
  • the conductive material according to the present invention can be used as a constituent material of the organic semiconductor layer 50.
  • the chemical structure of the group Y of the compound represented by the general formula (Al) it is possible to impart a desired carrier transport property to a resultant polymer (that is, to a conductive material according to the present invention) .
  • the conductive material according to the present invention is useful for forming an organic semiconductor layer 50 because it is possible to impart good semiconductivity to the polymer by appropriately setting the chemical structure of the group Y.
  • a polymer of the compound represented by the general formula (Al) in which the group Y has a chemical structure represented by any one of the chemical formulas (D2), (D3), (D16), (D17) and (D20) is preferably selected.
  • the thickness of the organic semiconductor layer 50 is preferably in the range of about 0.1 to 1,000 nm, more preferably in the range of about 1 to 500 nm, and even more preferably in the range of about 10 to 100 nm.
  • the organic semiconductor layer 50 which is obtained by using a polymer such as the conductive material according to the present invention as its main material, it is possible to obtain an organic TFT 10 having reduced size and weight. In addition, it is also possible for the organic TFT 10 to have excellent flexibility. Such an organic TFT 10 is suitably used for a switching element of a flexible display provided with the organic EL devices described above.
  • the organic semiconductor layer 50 is not limited to one provided so as to cover the source electrode 30 and the drain electrode 40.
  • the organic semiconductor layer 50 should be provided in at least the region between the source electrode 30 and the drain electrode 40 (that is, in at least the channel region 510) .
  • the gate insulating layer 60 is provided on the organic semiconductor layer 50.
  • the gate insulating layer 60 is provided to insulate the gate electrode 70 from the source electrode 30 and the drain electrode 40.
  • the gate insulating layer 60 is preferably formed using an organicmaterial (especially, an organic polymericmaterial) as its main material.
  • an organic material especially, an organic polymericmaterial
  • organic polymeric material examples include polystyrene, polyimide, polyamideimide, polyvinylphenylene, polycarbonate (PC), acrylic resins such as polymethylmethacrylate (PMMA), fluorinated resins such as polytetrafluoroethylene (PTFE), phenolic resins such as polyvinyl phenol and novolac resins, and olefin-based resins such as polyethylene, polypropylene, polyisobutylene, and polybutene.
  • acrylic resins such as polymethylmethacrylate (PMMA)
  • fluorinated resins such as polytetrafluoroethylene (PTFE)
  • phenolic resins such as polyvinyl phenol and novolac resins
  • olefin-based resins such as polyethylene, polypropylene, polyisobutylene, and polybutene.
  • the thickness of the gate insulating layer 60 is not particularly limited, but is preferably in the range of about 10 to 5,000 nm, more preferably in the range of about 100 to 1,000 nm. By setting the thickness of the gate insulating layer 60 to a value within the above range, it is possible to prevent the size of the organic TFT 10 from being increased (especially, an increase in thickness of the organic TFT 10) while reliably insulating the gate electrode 70 from the source electrode 3 and the drain electrode 40.
  • the gate insulating layer 60 is not limited to one comprised of a single layer and may have two or more layers.
  • the gate electrode 70 is provided on the gate insulating layer 60.
  • constituent materials of the gate electrode 70 the same constituent materials that have been mentioned with reference to the source electrode 30 and the drain electrode 40 can be used.
  • the thickness of the gate electrode 70 is not particularly limited, but is preferably in the range of about 0.1 to 5,000 nm, more preferably in the range of about 1 to 5,000 nm, even more preferably in the range of about 10 to 5,000 nm.
  • the amount of current flowing between the source electrode 30 and the drain electrode 40 is controlled by changing voltage applied to the gate electrode 70.
  • Such an organic TFT 10 as described above can be manufactured in the following manner, for example.
  • FIGs. 3 and 4 are drawings (cross-sectional views) to be used for explaining a manufacturing method of the organic TFT 10 shown in FIG. 2. It is to be noted that, in the following description, the upper side and lower side in FIGs. 3 and 4 will be referred to as the “upper side” and the “lower side”, respectively.
  • a substrate 20 as shown in FIG. 3 (a) is prepared.
  • the substrate 20 is washed with, for example, water (e.g. , pure water) and/or organic solvents.
  • Water and organic solvents may be used singly or in combination of two or more of them.
  • a photoresist is supplied onto the substrate 20 to form a film 80' (see FIG. 3 (b)).
  • a photoresist to be supplied onto the substrate 20 either a negative-type photoresist or a positive-type photoresist may be used.
  • the negative-type photoresist an area irradiated with light (that is, an area exposed to light) is cured and then an area other than the area exposed to light is dissolved by development to be removed.
  • the positive-type photoresist an area exposed to light is dissolved by development to be removed.
  • Examples of such a negative-type photoresist include water-soluble photoresists such as rosin-dichromate, polyvinyl alcohol (PVA) -di ⁇ hrom ' ate, shellac-dichromate. casein-dichromate, PVA-diazo, and acrylic photoresists and oil-soluble photoresists such as polyvinyl cinnamate, cyclized rubber-azide, polyvinyl cinnamylidene acetate, and polycinnamic acid ⁇ -vinyloxyethyl ester.
  • water-soluble photoresists such as rosin-dichromate, polyvinyl alcohol (PVA) -di ⁇ hrom ' ate, shellac-dichromate. casein-dichromate, PVA-diazo, and acrylic photoresists and oil-soluble photoresists such as polyvinyl cinnamate, cyclized rubber-azide
  • Examples of a positive-type photoresist include oil-soluble photoresists such as o-naphthoquinonediazide.
  • Any method can be used for supplying a photoresist onto the substrate 20, but various application methods are preferably employed.
  • the film 80 ' is exposed to light through a photomask and is then developed to form a resist layer 80 having openings 820 where a source electrode 30 and a drain electrode 40 are to be formed (see FIG. 3(C)).
  • a predetermined amount of a liquid material 90 containing a constituent material of a source electrode 30 and a drain electrode 40 to be formed or a precursor thereof is supplied to the openings 820 provided on the substrate 20.
  • solvents or dispersion media in which a constituent material of a source electrode 30 and a drain electrode 40 or a precursor thereof is dissolved or dispersed for preparing a liquid material 90 the same solvents or dispersion media that have been mentioned with reference to the step of forming hole transport layer [A2] can be used.
  • an inkjet method that is, a liquid droplet ejecting method
  • a liquid droplet ejecting method By employing the inkjet method, it is possible to eject the liquid material 90 in the form of liquid droplets from a nozzle of a liquid droplet ejecting head, thereby enabling the liquid material 90 to be reliably supplied to the openings 820. As a result, adhesion of the liquid material 90 to the resist layer 80 is reliably prevented.
  • the solvent or dispersion medium contained in the liquid material 90 supplied to the openings 820 is removed to form a source electrode 30 and a drain electrode 40.
  • the temperature at which the solvent or dispersion medium is removed is not particularly limited, and slightly varies depending on the kind of solvent or dispersion medium used. However, the temperature at which the solvent or dispersion medium is removed is preferably in the range of about 20 to 200°C, more preferably in the range of about 50 to 100 0 C. By removing the solvent or dispersion medium at a temperature within the above range, it is possible to reliably remove the solvent or dispersion medium from the liquid material 90.
  • the solvent or dispersion medium contained in the liquid material 90 may be removed by heating under reduced pressure. By doing so, it is possible to more reliably remove the solvent or dispersion medium from the liquid material 90.
  • the resist layer 80 provided on the substrate 20 is removed to obtain the substrate 20 on which the source electrode 30 and the drain electrode 40 are formed (see FIG. 4(a)).
  • Amethod for removing the resist layer 80 is appropriately selected depending on the kind of resist layer 80.
  • ashing such as plasma treatment or ozone treatment, irradiation with ultraviolet rays, or irradiation with a laser such as a Ne-He laser, an Ar laser, a CO 2 laser, a ruby laser, a semiconductor laser, a YAG laser, a glass laser, a YVO 4 laser, or an excimer laser may be carried out.
  • the resist layer 80 may removed by being brought into contact with a solvent capable of dissolving or decomposing the resist layer 80 by, for example, immersing the resist layer 80 in such a solvent.
  • an organic semiconductor layer 50 is formed on the substrate 20 so as to cover the source electrode 30 and the drain electrode 40 provided on the substrate 20.
  • a channel region 510 is formed between the source electrode 30 and the drain electrode 40 (that is, in an area corresponding to an area where a gate electrode 70 is to be formed) .
  • the organic semiconductor layer 50 can be formed by the same methods as those described with reference to the step of forming the hole transport layer [A2] in the manufacturing method of the organic EL device 1.
  • the organic semiconductor layer 50 is formed using the conductive material (that is, the polymer) according to the present invention as its main material. Therefore, when a gate insulating layer material is supplied onto the organic semiconductor layer 50 in the next step [B3], swelling and dissolution of the polymer due to a solvent or dispersion medium contained in the gate insulating layer material is properly inhibited or prevented. As a result, mutual dissolution between the organic semiconductor layer 50 and a gate insulating layer 60 is reliably prevented.
  • the conductive material that is, the polymer
  • a gate insulating layer 60 is formed on the organic semiconductor layer 50 by an application method.
  • the gate insulating layer 60 can be formed by applying or supplying a solution containing an insulating material or a precursor thereof onto the organic semiconductor layer 50 by the application method described above.
  • the thus obtained layer is subjected to aftertreatment such as heating, irradiationwith infraredrays, or exposure to ultrasound.
  • a gate electrode 70 is formed on the gate insulating layer 60 by an application method.
  • the gate electrode 70 can be formed by applying or supplying a solution containing an electrode material or a precursor thereof onto the gate insulating layer 60 by the applicationmethod.
  • the thus obtained layer is subjected to aftertreatment such as heating, irradiation with infrared rays, or exposure to ultrasound.
  • an inkjet method is preferably employed.
  • the inkjet method it is possible to eject a solution containing an electrode material or a precursor thereof in the form of liquid droplets from a nozzle of a liquid droplet ejectinghead to carry out patterning.
  • a gate electrode 70 having a predetermined shape is easily and reliably formed on the gate insulating layer 60.
  • the organic TFT 10 is manufactured through the steps described above.
  • the electronic devices according to the present invention such as the organic EL device (which is a light emitting device) 1 and the organic TFT (which is a switching element) 10 as described above can be used for various electronic equipment.
  • FIG. 5 is a perspective view which shows the structure of a personal mobile computer (or a personal notebook computer) to which the electronic equipment according to the present invention is applied.
  • a personal computer 1100 is comprised of a main body 1104 provided with a keyboard 1102 and a display unit 1106 provided with a display.
  • the display unit 1106 is rotatably supported by the main body 1104 via a hinge structure.
  • the display unit 1106 includes the organic EL device (which is a light emitting device) 1 and the organic TFT (which is a switching element) 10 described above.
  • FIG. 6 is a perspective view ' which shows the structure of a mobile phone (including the personal handyphone system (PHS)) to which the electronic equipment according to the present invention is applied.
  • PHS personal handyphone system
  • the mobile phone 1200 shown in FIG. 6 includes a plurality of operation buttons 1202, an earpiece 1204, a mouthpiece 1206, and a display.
  • the display includes the organic EL device (which is a light emitting device) 1 and the organic TFT (which is a switching element) 10 described above.
  • FIG. 7 is a perspective view which shows the structure of a digital still camera to which the electronic equipment accordingto thepresent invention is applied. In this drawing, interfacing to external devices is simply illustrated.
  • an image pickup device such as a CCD (Charge Coupled Device) generates an image pickup signal (or an image signal) by photoelectric conversion of the optical image of an object.
  • CCD Charge Coupled Device
  • the display which provides an image based on the image pickup signal generated by the CCD. That is, the display functions as a finder which displays the object as an electronic image.
  • the display includes the organic EL device (which is a light emitting device) 1 and the organic TFT (which is a switching element) 10 described above.
  • the circuit board 1308 has a memory capable of storing an image pickup signal.
  • a light receiving unit 1304 including an optical lens (an image pickup optical system) and a CCD.
  • an image pickup signal generated by the CCD at that time is transferred to the memory in the circuit board 1308 and then stored therein.
  • a video signal output terminal 1312 and an input-output terminal for data communication 1314 there are provided a video signal output terminal 1312 and an input-output terminal for data communication 1314.
  • a television monitor 1430 and a personal computer 1440 are connected to the video signal output terminal 1312 and the input-output terminal for data communication 1314, respectively.
  • an image pickup signal stored in the memory of the circuit board 1308 is outputted to the television monitor 1430 or the personal computer 1440 by carrying out predetermined operation.
  • the electronic equipment according to the present invention can be applied not only to the personal computer (which is apersonal mobile computer) shown in FIG.5, the mobile phone shown in FIG. 6, and the digital still camera shown in FIG. 7 but also to a television set, avideo camera, a view-finer or monitor type of video tape recorder, a laptop-type personal computer, a car navigation device, a pager, an electronic notepad (which may have communication facility) , an electronic dictionary, an electronic calculator, a computerized game machine, a word processor, a workstation, a videophone, a security television monitor, an electronic binocular, a POS terminal, an apparatus providedwith a touch panel (e.g., a cash dispenser located on a financial institute, a ticket vending machine), medical equipment (e.g., an electronic thermometer, a sphygmomanometer, a blood glucose meter, an electrocardiograph monitor, ultrasonic diagnostic equipment, an endoscope monitor) , a fish detector, various measuring instruments, gages (e
  • the conductive material, the composition for the conductive material, the conductive layer, the electronic device, and the electronic equipment according to the present invention have been described based on the embodiments shown in the drawings, but the present invention is not limited thereto.
  • the electronic device according to the present invention has a hole transport layer as a conductive layer
  • such an electronic device can be used for, for example, a solar cell that is an example of light receiving devices (or photoelectric transducers) as well as the organic EL device as described above that is an example of display devices (or light emitting devices).
  • the electronic device according to the present invention has an organic semiconductor layer as a conductive layer
  • such an electronic device can be used for, for example, a semiconductor device as well as the organic TFT as described above that is an example of switching elements.
  • the conductive layer according to the present invention can be used as, for example, wiring or an electrode as well as the hole transport layer as described above.
  • a resultant electronic device according to the present invention can be used for a wiring board and the like.
  • the thus obtained compound was then reduced by hydrogen gas under Pd-C catalyst so that transformation was made from the benzyl ether group to the hydroxyl group to carry out deprotection, and then it was allowed to cool for crystallization to obtain a compound. Then, the thus obtained compound was confirmed to be the following compound (AI) bymeans of amass spectrum (MS) method, a """H-nuclear magnetic resonance ( 1 H-NMR) spectrum method, a 13 C-nuclear magnetic resonance ( 13 C-NMR) spectrum method, and a Fourier transform infrared absorption (FT-IR) spectrum method.
  • MS amass spectrum
  • 1 H-NMR 13 C-nuclear magnetic resonance
  • 13 C-NMR 13 C-nuclear magnetic resonance
  • FT-IR Fourier transform infrared absorption
  • a compound (BI) was obtained in the same manner as the compound (AI) except that l-bromo-4-hexylbenzene was changed to l-bromo-3,5-dimethyl-4 ⁇ hexylbenzene.
  • a compound (CI) was obtained in the same manner as the compound (AI) except that 6-(p-aminophenyl)hexanol was changed to 2-(p-aminophenyl)ethanol and l-bromo-4-hexylbenzene was changed to l-bromo-4-ethylbenzene, respectively.
  • a compound (EI) was obtained in the same manner as the compound (AI) except that 6- (p-aminophenyl)hexanol was changed to 8-(p-aminophenyl)octanol and l-bromo-4-hexylbenzene was changed to l-bromo-4-octylbenzene, respectively.
  • a compound (FI) was obtained in the same manner as the compound (AI) except that 6-(p-aminophenyl)hexanol was changed to 1- (p-aminophenyl)methanol and l-bromo-4-hexylbenzene was changed to 4-bromotoluene, respectively.
  • a compound (BII) was obtained in the same manner as the compound (All) except that l-bromo-4-hexylbenzene was changed to l-bromo-3,5-dimethyl-4-hexylbenzene.
  • a compound (CII) was obtained in the same manner as the compound (All) except that 6- (p-aminophenyl)hexanol was changed to 2- (p-aminophenyl)ethanol and l-bromo-4-hexylbenzene was changed to l-bromo-4-ethylbenzene, respectively.
  • a compound (DII) was obtained in the same manner as the compound (CII) except that 2,5-bis(4-iodophenyl) -thiophene was changed to 2,5-bis(2-methyl-4-iodophenyl)-thiophene.
  • a compound (EII) was obtained in the same manner as the compound (All) except that 6-(p-aminophenyl)hexanol was changed to 8-(p-aminophenyl)octanol and l-bromo-4-hexylbenzene was changed to l-bromo-4-octylbenzene, respectively.
  • a compound (FII) was obtained in the same manner as the compound (All) except that 6-(p-aminophenyl)hexanol was changed to 1-(p-aminophenyl)methanol and l-bromo-4-hexylbenzene was changed to 4-bromotoluene, respectively.
  • a compound (HII) was obtained in the same manner as the compound (All) except that 2,5-bis(4-iodophenyl) -thiophene was changed to 3,5-diiodo-l,2,4-triazole.
  • a compound (III) was obtained in the same manner as the compound (All) except that 2,5-bis(4-iodophenyl) -thiophene was changed to 2,5-(4-iodophenyl) -1,3,4-oxadiazole.
  • a compound (JII) was obtained in the same manner as the compound (All) except that 2,5-bis(4-iodophenyl) -thiophene was changed to 3,3' -diiodo-1, 1' -biisobenzothiophene.
  • a compound (KII) was obtained in the same manner as the compound (JII) except that 6-(p-aminophenyl)hexanol was changed to 2-(p-aminophenyl)ethanol and l-bromo-4-hexylbenzene was changed to l-bromo-4-ethylbenzene, respectively.
  • a compound (LII) was obtained in the same manner as the compound (JII) except that 6-(p-aminophenyl)hexanol was changed to 8-(p-aminophenyl)octanol and l-bromo-4-hexylbenzene was changed to l-bromo-4-octylbenzene, respectively.
  • a compound (Mil) was obtained in the same manner as the compound (JII) except that 6- (p-aminophenyl)hexanol was changed to 1-(p-aminophenyl)methanol and l-bromo-4-hexylbenzene was changed to 4-bromotoluene, respectively.
  • a compound (Oil) was obtained in the same manner as the compound (All) except that 2,5-bis(4-iodophenyl)-thiophene was changed to 5, 5' ' -diiodo-2,2' :5' ,2' ' -ter-selenophene.
  • a compound (PII) was obtained in the same manner as the compound (All) except that 2,5-bis(4-iodophenyl) -thiophene was changed to
  • the thus obtained compound was found to be the following compound (QII) bymeans of amass spectrum (MS) method, a ⁇ -nuclear magnetic resonance ( 1 H-NMR) spectrum method, a 13 C-nuclear magnetic resonance ( 13 C-NMR) spectrum method, and a Fourier transform infrared absorption (FT-IR) spectrum method.
  • MS amass spectrum
  • 1 H-NMR ⁇ -nuclear magnetic resonance
  • 13 C-NMR 13 C-nuclear magnetic resonance
  • FT-IR Fourier transform infrared absorption
  • a compound (SII) was obtained in the same manner as the compound (QII) except that 2,5-bis(4-iodophenyl) -thiophene was changed to 3,5-diiodo-l,2,4-triazole.
  • Example IA preparation of hole transport material>
  • the compound (AI) was used as an arylamine derivative, pyridine was used as a base, and tetrahydrofuran (THF) was used as an organic solvent, respectively, and then the compound (AI) was dissolved in a mixed solution of the pyridine solution and the THF in a volume ratio of 5:1 to prepare a hole transport material.
  • an ITO electrode that is, an anode
  • a transparent glass substrate having an average thickness of 0.5 mmbyvacuumevaporation so as tohave an average thickness of 100 nm.
  • the glass substrate onwhich the ITO electrode was formed was placed in a chamber, and then the hole transport material was applied onto the ITO electrode by a spin coating method.
  • an electron transport layer having an average thickness of 20 nm was formed on the light emitting layer by vacuum evaporation of 3,4, 5-triphenyl-l,2,4-triazole.
  • an AlLi electrode that is, a cathode
  • an AlLi electrode that is, a cathode
  • a protection cover made of polycarbonate was provided so as to cover these layers described above, and was then secured and sealed with an ultraviolet curable resin to obtain an organic EL device.
  • the compound (AI) was used as an arylamine derivative, and diethyl carbonate was used as a phosgene derivative, respectively, and then the compound (AI) and the diethyl carbonate were dissolved in a solution of tetrahydrofuran (THF) to prepare a hole transport material (a composition for the conductive material).
  • THF tetrahydrofuran
  • the mixing ratio of the compound (AI) to the diethyl carbonate was 1:4 in a mole ratio.
  • Organic EL devices were manufactured in the same manner as in Example IA except that the hole transport material applied onto the ITO electrode in the above described step 2A was subjected to a heat treatment in a nitrogen gas atmosphere with the treatment conditions at a temperature of 150°C and apressure of 10 3 Pa for 30 minutes so that the hydrated alkyl group of the compound (AI) was allowed to make ester exchange reaction with the diethyl carbonate to thereby form a hole transport layer having an average thickness of 50 nm.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example IA except that as for the arylamine derivatives, the compound (BI) was used.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example 2A except that as for the arylamine derivatives, the compound (BI) was used.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example IA except that as for the arylamine derivatives, the compound (CI) was used.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example 2A except that as for the arylamine derivatives, the compound (CI) was used.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example IA except that as for the arylamine derivatives, the compound (DI) was used.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example 2A except that as for the arylamine derivatives, the compound (DI) was used.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example IA except that as for the arylamine derivatives, the compound (EI) was used.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example 2A except that as for the arylamine derivatives, the compound (EI) was used.
  • Organic EL devices were manufactured in the same manner as in Example IA except that the hole transport layer was formed by drying the hole transport material applied (supplied) onto the ITO electrode in the step 2A.
  • the compound (RII) was dispersed in water to prepare a
  • Organic EL devices were manufactured in the same manner as in Comparative Example IA except that the hole transport material was changed to the hole transport material prepared in this Comparative Example 2A.
  • the compound (AI) was used as an arylamine derivative, and the compound (AI) and a polycarbonate resin ("Panlite L 1250" produced by Teijin Chemicals LTD.) in a weight ratio of 3: 7 were mixed with dichloroethane to prepare a hole transport material.
  • Organic EL devices were manufactured in the same manner as in Comparative Example IA except that the hole transport material was changed to the hole transport material prepared in this Comparative Example 3A.
  • the compound (GI) was used as an arylamine derivative, and a bisphenol A epoxy compound ("ADEKA RESIN EP” produced by ASAHI DENKA CO., LTD.) was used as a photocrosslinking agent, and then the compound (GI) , the bisphenol A epoxy compound and a cationic photopolymerization initiator ( "FC-508" produced by Sumitomo 3M Limited) in a weight ratio of 85:14:1 were mixed with dichloroethane to obtain a hole transport material.
  • a bisphenol A epoxy compound (“ADEKA RESIN EP” produced by ASAHI DENKA CO., LTD.
  • FC-508 cationic photopolymerization initiator
  • Organic EL devices were manufactured in the same manner as in Example IA except that the hole transport layer was formed by drying the hole transport material applied (supplied) onto the ITO electrode in the step 2A, irradiating the dried hole transport material in an atmosphere with ultraviolet rays having a wavelength of 365 nm from a mercury lamp ("UM-452", USHIO Inc.) through a filter at an intensity of irradiation of 400 mW/cm 2 for 10 seconds, and then heating the hole transport material at a temperature of 110 0 C for 60 minutes.
  • a mercury lamp "UM-452", USHIO Inc.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example IA except that as for the arylamine derivatives, the compound (FI) was used.
  • Organic EL devices were manufactured after a hole transport material was prepared in the same manner as in Example 2A except that as for the arylamine derivatives, the compound (FI) was used.
  • the compound (All) was used as an arylamine derivative, pyridine was used as a base, and tetrahydrofuran (THF) was used as an organic solvent, respectively, and then the compound (All) was dissolved in a mixed solution of the pyridine solution and the THF in a volume ratio of 5:1 to prepare a hole transport material.
  • An electron transport material (that is, a composition for the conductive material) was obtained in the same manner as the hole transport material prepared in this Example except that the compound (HII) was used as an arylamine derivative.
  • an ITO electrode that is, an anode
  • a transparent glass substrate so as to have an average thickness of 100 nm in the same manner as the step IA.
  • the glass substrate onwhich the ITO electrode was formed was placed in a chamber, and then the prepared hole transport material was applied onto the ITO electrode by a spin coating method.
  • the inside of the closed chamber where the hole transport material was placed was maintained at a temperature of 0 0 C and phosgene was introduced thereinto so as to establish a pressure of 10 5 Pa (at 0 0 C) .
  • phosgene was introduced thereinto so as to establish a pressure of 10 5 Pa (at 0 0 C) .
  • an electron transport layer having an average thickness of 20 nm was formed on the light emitting layer by polycondensation reaction of the hydrated alkyl group of the compound (HII) and phosgene in the same manner as the above described step 2B excepting that the prepared electron transport material was used instead of the hole transport material
  • an AlLi electrode that is, a cathode
  • an AlLi electrode that is, a cathode
  • organic EL devices were manufactured after a hole transport material and an electron transport material were prepared using the phosgene method in the same manner as in Example IB except that as for the arylamine derivatives for use in the hole transport material and the electron transport material, the compounds shown in Table 2 were used, respectively.
  • ⁇ Preparation of hole transport material> The compound (All) was used as an arylamine derivative, and diethyl carbonate was used as a phosgene derivative, respectively, and then the compound (All) and the diethyl carbonatewere dissolved in a solution of tetrahydrofuran (THF) to prepare a hole transport material (a composition for the conductive material) .
  • THF tetrahydrofuran
  • the mixing ratio of the compound (All) to the diethyl carbonate was 1:4 in a mole ratio.
  • An electron transport material (that is, a composition for the conductive material) was obtained in the same manner as the hole transport material prepared in this Example except that the compound (HII) was used as an arylamine derivative.
  • Organic EL devices were manufactured in the same manner as in Example IB except that the hole transport material applied onto the ITO electrode in the above described step 2B was subjected to a heat treatment in a nitrogen gas atmosphere with the treatment conditions at a temperature of 150°C and apressure of 10 3 Pa for 30 minutes so that the hydrated alkyl group of the compound (All) was allowed to make ester exchange reaction with the diethyl carbonate to thereby form a hole transport layer having an average thickness of 50 nm, and in addition the electron transport material applied onto the light emitting layer in the above described step 4B was subjected to a heat treatment in a nitrogen gas atmosphere with the treatment conditions at a temperature of 150°C and a pressure of 10 3 Pa for 30 minutes so that the hydrated alkyl group of the compound (HII) was allowed to make ester exchange reaction with the diethyl carbonate to thereby form an electron transport layer having an average thickness of 20 nm.
  • Organic EL devices were manufactured in the same manner as in Example IB except that the hole transport layer was formed by drying the hole transport material applied (supplied) onto the ITO electrode in the above described step 2B, and the electron transport layer was formed by the vacuum evaporation of the compound (SII) in the above described step 4B.
  • the compound (RII) was dispersed in water to prepare a
  • Organic EL devices were manufactured in the same manner as in Comparative Example IB except that the hole transport material was changed to the hole transport material prepared in this Comparative Example.
  • the compound (All) was used as an arylamine derivative, and the compound (All) and a polycarbonate resin ("Panlite L 1250" produced by Teijin Chemicals LTD.) in a weight ratio of 3:7 were mixed with dichloroethane to prepare a hole transport material.
  • a polycarbonate resin "Panlite L 1250" produced by Teijin Chemicals LTD.
  • Organic EL devices were manufactured in the same manner as in Example IB except that the hole transport layer was formed by drying the hole transport material applied (supplied) onto the ITO electrode in the above described step 2B, and the electron transport layer was formed by drying the electron transport material applied (supplied) onto the light emitting laeyr.
  • the compound (QII) was used as an arylamine derivative, and a bisphenol A epoxy compound ("ADEKA RESIN EP” produced by ASAHI DENKA CO., LTD.) was used as a photocrosslinking agent, and then the compound (QII) , the bisphenol A epoxy compound and a cationic photopolymerization initiator ( "FC-508" produced by Sumitomo 3M Limited) in a weight ratio of 85:14:1 were mixed with dichloroethane to obtain a hole transport material.
  • a bisphenol A epoxy compound (“ADEKA RESIN EP” produced by ASAHI DENKA CO., LTD.) was used as a photocrosslinking agent, and then the compound (QII) , the bisphenol A epoxy compound and a cationic photopolymerization initiator ( "FC-508" produced by Sumitomo 3M Limited) in a weight ratio of 85:14:1 were mixed with dichloroethane to obtain a hole transport material.
  • An electron transport material was obtained in the same manner as the hole transport material prepared in this Comparative Example except that the compound (SII) was used as an arylamine derivative.
  • Organic EL devices were manufactured in the same manner as in Example IB except that the hole transport layer was formed by drying the hole transport material applied (supplied) onto the ITO electrode in the step 2B, irradiating the dried hole transport material in an atmosphere with ultraviolet rays having a wavelength of 365 nm from a mercury lamp ("UM-452", USHIO Inc. ) through a filter at an intensity of irradiation of 400 mW/cm 2 for 10 seconds, and then heating the hole transport material at a temperature of 110 0 C for 60 minutes to form a hole transport layer.
  • UM-452 ultraviolet rays having a wavelength of 365 nm from a mercury lamp ("UM-452", USHIO Inc. ) through a filter at an intensity of irradiation of 400 mW/cm 2 for 10 seconds
  • the electron transport layer was formed by drying the electron transport material applied onto the light emitting layer in the above described step 4B, irradiating the dried electron transport material in an atmosphere with ultraviolet rays having a wavelength of 365 nm using the same mercury lamp at an intensity of irradiation of 400 mW/cm 2 for 10 seconds, and. then heating the electron transport material at a temperature of 110°C for 60 minutes to form an electron transport layer.
  • Organic EL devices were manufactured in the same manner as in Example IB except that a hole transport layer was formed using the hole transport material obtained in this Comparative Example, and the electron transport layer was formed by the vacuum evaporation of the compound (SII) in the above described step 4B.
  • Organic EL devices were manufactured in the same manner as in Example 14B except that a hole transport layer was formed using the hole transport material obtained in this Comparative Example, and the electron transport layer was formed by the vacuum evaporation of the compound (SII) in the above described step 4B.
  • the luminous brightness (cd/m 2 ), the maximum luminous efficiency (lm/W) , and the time that elapsedbefore the luminous brightness became half of the initial value (that is, a half-life) of each of the organic EL devices obtained in the Examples and the Comparative Examples mentioned above were measured. Based on the measurement values for the five organic EL devices, an average was calculated.
  • the luminous brightness was measured by applying a voltage of 6V across the ITO electrode and the AlLi electrode.
  • the measurement values (that is, the luminous brightness, the maximum luminous efficiency, and the half-life) of each of the Examples IA to 1OA and the Comparative Examples 2A to 6A were evaluated based on the measurement values of the Comparative Example IA according to the following four criteria, respectively.
  • Themeasurement values (that is, the luminous brightness, the maximum luminous efficiency, and the half-life) of each of the Examples IB to 26B and the Comparative Examples 2B to 6B were evaluated based on the measurement values of the Comparative Example IB according to the following four criteria, respectively.
  • the conductive materials of the Examples which were formed of the compounds containing the substituents X 1 each having an appropriate n 1 value in the general formula (A2) that is the conductive materials formed of the compounds containing the substituents X 1 by which the adjacent main skeletons are allowed to exist at a suitable interval, could have more superior luminous brightness, maximum luminous efficiency, and half-life as compared to the conductive materials which do not have such a substituent X 1 .
  • the organic EL devices in the Examples each obtained by appropriately selecting conductive materials for respectively constituting the hole transport material and the electron transport material namely, the organic EL devices in the Examples each having a preferred combination of the hole transport layer and the electron transport layer by appropriately selecting the group Y of the compound represented by the above-mentioned general formula (Al) couldhave superior luminous brightness, maximum luminous efficiency, and half-life.
  • Example 1C preparation of organic semiconductor material>
  • the compound (JII) was used as an arylamine derivative, pyridine was used as a base, and tetrahydrofuran (THF) was used as an organic solvent, respectively, and then the compound (JII) was dissolved in a mixed solution of the pyridine solution and the THF in a volume ratio of 5:1 to prepare an organic semiconductor material.
  • a glass substrate having an average thickness of 1 mm was prepared, and it was then washedwithwater (that is, with a cleaning fluid).
  • a photoresist was applied onto the glass substrate by a spin coating method, and then the photoresist was prebaked to form a film.
  • the film was irradiated with (or exposed to) ultraviolet rays through a photomask to develop it. In this way, a resist layer having openings where a source electrode and a drain electrode were to be provided was formed.
  • an aqueous gold colloidal solution was supplied to the openings by an inkjet method. Then, the glass substrate to which the aqueous gold colloidal solution had been supplied was dried by heating to obtain a source electrode and a drain electrode.
  • the resist layer was removed by oxygen plasma treatment. Then, the glass substrate on which the source electrode and the drain electrode had been formed was washed with water, and was then washed with methanol.
  • the glass substrate on which the source electrode and the drain electrode was placed in a chamber was placed in a chamber, and then the prepared organic semiconductor material was applied onto the glass substrate by a spin coating method.
  • phosgene was introduced into the chamber which was being kept at a temperature of 0 0 C and in which the organic semiconductor material was placed so that the internal pressure became 10 5 Pa (at 0°C) , and then such a state was being kept for one hour so that hydrated alkyl group of the compound (JII) was allowed to make polycondensation reaction with phosgene. Thereafter, the organic semiconductor material was dried to obtain an organic semiconductor layer having an average thickness of 50 nm.
  • a butyl acetate solution of polymethylmethacrylate (PMMA) was applied onto the organic semiconductor layer by a spin coating method, andwas then dried to form a gate insulating layer having an average thickness of 500 nm.
  • PMMA polymethylmethacrylate
  • a water dispersion of polyethylenedioxythiophene was applied to an area on the gate insulating layer corresponding to the area between the source electrode and the drain electrode by an inkjet method, and was then dried to form a gate electrode having an average thickness of 100 nm.
  • organic TFTs were manufactured after the organic semiconductor material was prepared in the same manner as in Example 1C except that as for an arylamine derivative for use in preparing the organic semiconductor material, those shown in Table 3 were used.
  • Organic TFTs were manufactured after the organic semiconductor material was prepared in the same manner as in Example 14A of the hole transport material except that the compound (JII) was used as an arylamine derivative.
  • Organic TFTs were manufactured in the same manner as in Example 1C except that the organic semiconductor layer was formed by subjecting the organic semiconductor material which was applied (supplied) onto the glass substrate and prepared in this Example in the above described step 4C to aheat treatment in a nitrogen gas atmosphere with the treatment conditions at a temperature of 15O 0 C and a pressure of 10 3 Pa for 30 minutes so that the hydrated alkyl group of the compound (JII) was allowed to make ester exchange reaction with the diethyl carbonate to thereby form an organic semiconductor layer having an average thickness of 50 nm.
  • organic TFTs were manufactured in the same manner as in Example 8C using the ester exchange method except that as for the arylamine derivative for use in the organic semiconductor material, those shown in Table 3 were used.
  • Organic TFTs were manufactured in the same manner as in Example 1C except that by drying the organic semiconductor material prepared in this Comparative Example and applied onto the glass substrate on which the source electrode and the drain electrode were formed, an organic semiconductor layer was formed.
  • the compound (JII) was used as an arylamine derivative, and the compound (JII) and a polycarbonate resin ("Panlite L
  • Organic TFTs were manufactured, in the same manner as in Example 1C except that as for the organic semiconductormaterial, the organic semiconductormaterial preparedin this Comparative Example was used.
  • Organic TFTs were manufactured in the same manner as in Example 1C except that the organic semiconductor layer was formed by drying the organic semiconductor material applied (supplied) onto the ITO electrode in the step 4C, irradiating the dried organic semiconductor material in an atmosphere with ultraviolet rays having a wavelength of 365 nm from a mercury lamp ("UM-452", USHIO Inc.) through a filter at an intensity of irradiation of 400 mW/cm 2 for 10 seconds, and then heating the organic semiconductor material at a temperature of 110°C for 60 minutes.
  • UM-452 ultraviolet rays having a wavelength of 365 nm from a mercury lamp ("UM-452", USHIO Inc.)
  • Organic TFTs were manufactured after the organic semiconductor material was prepared in the same manner as in Example 1C except that as for the arylamine derivative for use in the organic semiconductor material the compound (Mil) was used.
  • Organic TFTs were manufactured after the organic semiconductor material was prepared in the same manner as in Example 8C except that as for the arylamine derivative for use in the organic semiconductor material the compound (Mil) was used.
  • the word “OFF-state current” means the value of current flowing between the source electrode and the drain electrode when a gate voltage is not applied
  • the word “ON-state current” means the value of current flowing between the source electrode and the drain electrode when a gate voltage is applied.
  • a larger value of ratio of the absolute value of the ON-state current to the absolute value of the OFF-state current means that an organic TFT has better characteristics.
  • the OFF-state current was measured at a potential difference between the source electrode and the drain electrode of 30 V
  • the ON-state current was measured at a potential difference between the source electrode and the drain electrode of 30 V and an absolute value of gate voltage of 40 V.
  • A The value of ON/OFF ratio was 10 4 or more.
  • the polymer contained in the conductive material has a structure in which main skeletons of compounds are repeatedly bonded or linked through a chemical structure which is produced by the polycondensation reaction between the substituents X 1 of the compounds and phosgene represented by the chemical formula COCl 2 or its derivative, that is, a structure in which adjacent main skeletons are allowed to exist at a suitable interval repeatedly. Therefore, it is possible to decrease the interaction between the adjacent main skeletons in the polymer.
  • the constituent material of the conductive layer from such a polymer, when an upper layer is formed on the conductive layer using a liquid material, it is possible to properly suppress or prevent the polymer from being swelled or dissolved by the solvent or dispersion medium contained in the liquid material. As a result, it is possible to prevent mutual dissolution from occurring between the conductive layer and the upper layer to be formed.
  • the polymer can exhibit a high carrier transport ability, and thus a conductive material constituted from the polymer as its main material can also have a high carrier transport ability. Consequently, both an electronic device provided with such a conductive layer and electronic equipment provided such an electronic device can have high reliability. Therefore, the present invention has industrial adaptability required by PCT.

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Abstract

L'objet de la présente invention est de proposer un matériau conducteur ayant une grande capacité de transport de porteuse, une composition pour le matériau conducteur à partir duquel une couche conductrice ayant une grande capacité de transport de porteuse peut être fabriquée, un matériau conducteur formé de la composition et ayant une grande capacité de transport de porteuse, une couche conductrice formée à l’aide du matériau conducteur comme principal matériau, un dispositif électronique fourni avec la couche conductrice et ayant une fiabilité élevée et un équipement électronique pourvu du dispositif électronique. Le matériau conducteur de la présente invention est obtenu par une réaction de polycondensation des substituants X1 des composés, chacun représenté par la formule générale suivante (A1) via du phosgène et/ou son dérivé pour lier les composés : où deux R1 peuvent être identiques ou différents et chacun indépendamment représente un groupe alkyle à chaîne linéaire ayant de 2 à 8 atomes de carbone, quatre R2 peuvent être identiques ou différents et chacun représente indépendamment un atome d’hydrogène, un groupe méthyle ou un groupe éthyle, Y représente un groupe contenant au moins un anneau d’hydrocarbure aromatique substitué ou non ou un hétérocycle substitué ou non et deux X1 peuvent être identiques ou différents et chacun indépendamment représente un substituant représenté par la formule générale suivante (A2) : où n1 est un entier compris entre 2 et 8.
PCT/JP2005/023102 2004-12-13 2005-12-09 Materiau conducteur, composition pour le materiau conducteur, couche conductrice et dispositif et equipement electroniques Ceased WO2006064896A1 (fr)

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US8618561B2 (en) 2006-06-24 2013-12-31 Qd Vision, Inc. Methods for depositing nanomaterial, methods for fabricating a device, and methods for fabricating an array of devices
US9006753B2 (en) 2006-09-12 2015-04-14 Qd Vision, Inc. Electroluminescent display useful for displaying a predetermined pattern
US9054329B2 (en) 2006-06-02 2015-06-09 Qd Vision, Inc. Light-emitting devices and displays with improved performance
US9096425B2 (en) 2006-06-24 2015-08-04 Qd Vision, Inc. Methods for depositing nanomaterial, methods for fabricating a device, methods for fabricating an array of devices and compositions

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US4801517A (en) * 1987-06-10 1989-01-31 Xerox Corporation Polyarylamine compounds and systems utilizing polyarylamine compounds
US4935487A (en) * 1987-06-10 1990-06-19 Xerox Corporation Carbonate-arylamine polymer
US5698359A (en) * 1997-01-13 1997-12-16 Xerox Corporation Method of making a high sensitivity visible and infrared photoreceptor
US5976418A (en) * 1998-11-05 1999-11-02 Xerox Corporation Conducting compositions

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US4801517A (en) * 1987-06-10 1989-01-31 Xerox Corporation Polyarylamine compounds and systems utilizing polyarylamine compounds
US4935487A (en) * 1987-06-10 1990-06-19 Xerox Corporation Carbonate-arylamine polymer
US5698359A (en) * 1997-01-13 1997-12-16 Xerox Corporation Method of making a high sensitivity visible and infrared photoreceptor
US5976418A (en) * 1998-11-05 1999-11-02 Xerox Corporation Conducting compositions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9054329B2 (en) 2006-06-02 2015-06-09 Qd Vision, Inc. Light-emitting devices and displays with improved performance
US9853184B2 (en) 2006-06-02 2017-12-26 Samsung Electronics Co., Ltd. Light-emitting devices and displays with improved performance
US10770619B2 (en) 2006-06-02 2020-09-08 Samsung Electronics Co., Ltd. Light-emitting devices and displays with improved performance
US8618561B2 (en) 2006-06-24 2013-12-31 Qd Vision, Inc. Methods for depositing nanomaterial, methods for fabricating a device, and methods for fabricating an array of devices
US9096425B2 (en) 2006-06-24 2015-08-04 Qd Vision, Inc. Methods for depositing nanomaterial, methods for fabricating a device, methods for fabricating an array of devices and compositions
US9006753B2 (en) 2006-09-12 2015-04-14 Qd Vision, Inc. Electroluminescent display useful for displaying a predetermined pattern

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