Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/04—Ortho-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
  • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
  • C07F15/0046—Ruthenium compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
  • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
  • H05B33/00—Electroluminescent light sources
  • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
  • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
• • 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
  • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
  • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1003—Carbocyclic compounds
  • C09K2211/1007—Non-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1003—Carbocyclic compounds
  • C09K2211/1011—Condensed systems
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1003—Carbocyclic compounds
  • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1018—Heterocyclic compounds
  • C09K2211/1025—Heterocyclic compounds characterised by ligands
  • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1018—Heterocyclic compounds
  • C09K2211/1025—Heterocyclic compounds characterised by ligands
  • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1018—Heterocyclic compounds
  • C09K2211/1025—Heterocyclic compounds characterised by ligands
  • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/18—Metal complexes
  • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K2101/00—Properties of the organic materials covered by group H10K85/00
  • H10K2101/10—Triplet emission
• • 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
  • H10K50/00—Organic light-emitting devices
  • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
  • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K50/00—Organic light-emitting devices
  • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
  • H10K50/14—Carrier transporting layers
• • 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
  • H10K85/30—Coordination compounds
  • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
  • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
• • 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
  • H10K85/30—Coordination compounds
  • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
  • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
• • 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

Definitions

• the present invention relates to a material for organic electroluminescence devices (organic EL devices) and an organic EL device using the material and, more particularly, to an organic EL device emitting bluish light with a high purity of color.
• an organic EL device which utilize organic substances are expected to be useful for application as an inexpensive full color display device of the solid light emission type having a great size and various developments on the organic EL devices are being conducted.
• an organic EL device has a construction comprising a light emitting layer and a pair of electrodes disposed at both sides of the light emitting layer.
• the light emission of the organic EL device is a phenomenon in which, when an electric field is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side, the electrons are recombined with the holes in the light emitting layer to form an excited state, and energy generated when the excited state returns to the ground state is emitted as light.
• chelate complexes such as tris(8quinolinolato)aluminum, coumarine derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives and oxadiazole derivatives are known. It has been reported that these light emitting materials emit light in the visible region of blue to red and it is expected that color display devices can be obtained by using these light emitting materials (for example, Japanese Patent Application Laid-Open Nos. Heisei 8(1996)239655, Heisei 7(1995)-138561 and Heisei 3(1991)-200289).
• a device using a phenylanthracene derivative as the material emitting blue light is disclosed in Japanese Patent Application Laid-Open No. Heisei 8(1996)-12600.
• the phenylanthracene derivative is used as the material emitting blue light and, in general, used as a laminate composed of a layer of the material emitting blue light and a layer of a complex of tris(8quinolinolato)aluminum (Alq).
• Alq tris(8quinolinolato)aluminum
• a device emitting blue light in which an amine-based aromatic compound is used for the light emitting layer is disclosed.
• the efficiency of light emission of this device is as insufficient as 2 to 4 cd/A.
• a device in which an azafluoranthene compound is added to the light emitting layer is disclosed.
• this device emits light of yellow to green and cannot emit blue light having a sufficiently high purity of color.
• the present invention is made to overcome the above problems and has an object of providing a material for organic EL devices which emits bluish light with excellent purity of color and an organic EL device utilizing the material.
• the present invention provides a material for organic electroluminescence devices which comprises a compound represented by following general formula (1) or (2):
• Cz represents a substituted or unsubstituted arylcarbazolyl group or carbazolylalkylene group
• A represents a group represented by following general formula (A):
• M and M′ each independently represent a heteroaromatic ring having 2 to 40 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring
• M and M′ may represent a same ring or different rings
• L represents a single bond, a substituted or unsubstituted aryl group or arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms
• p represents an integer of 0 to 2
• q represents an integer of 1 or 2
• r represents an integer of 0 to 2
• p+r represents an integer of 1 or greater
• n and m each represent an integer of 1 to 3.
• the present invention also provides an organic electroluminescence device comprising an anode, a cathode and an organic thin film layer comprising at least one layer and disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises a material for organic electroluminescence devices described above.
• the light emitting layer, the electron transporting layer or the hole transporting layer may comprise the above material for organic EL devices.
• the material for organic electroluminescence devices of the present invention comprises a compound represented by following general formula (1) or (2):
• Cz represents a substituted or unsubstituted arylcarbazolyl group or carbazolylalkylene group and n and m each represent an integer of 1 to 3.
• the aryl group in the arylcarbazolyl group has 6 to 30 carbon atoms.
• the aryl group include phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, pyrenyl group, fluorenyl group, biphenyl group and terphenyl group. Among these groups, phenyl group, naphthyl group, biphenyl group and terphenyl group are preferable.
• the alkylene group in the carbazolylalkylene group has 1 to 10 carbon atoms.
• the alkylene group include methylene group, ethylene group, propylene group, isopropylene group, n-butylene group, s-butylene group, isobutylene group, t-butylene group, n-pentylene group, n-hexylene group, n-heptylene group, n-octylene group, hydroxymethylene group, chloromethylene group and aminomethylene group.
• methylene group, ethylene group, propylene group, isopropylene group, n-butylene group, t-butylene group and n-pentylene group are preferable.
• A represents a group represented by the following general formula (A):
• M and M′ each independently represent a heteroaromatic ring having 2 to 40 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring, and M and M′ may represent the same ring or different rings.
• heteroaromatic ring having nitrogen atom examples include rings of pyridine, pyrimidine, pyrazine, triazine, aziridine, azaindolidine, indolidine, imidazole, indole, isoindole, indazole, purine, puteridine, ⁇ -carboline, naphthylidine, quinoxaline, terpyridine, bipyridine, acridine, phenanthroline, phenazine and imidazopyridine.
• rings of pyridine, terpyridine, pyrimidine, imidazopyridine and triazine are preferable.
• L represents a single bond, a substituted or unsubstituted aryl group or arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms.
• p represents an integer of 0 to 2
• q represents an integer of 1 or 2
• r represents an integer of 0 to 2
• p+r represents an integer of 1 or greater.
• Examples of the aryl group having 6 to 30 carbon atoms include phenyl group, biphenyl group, terphenyl group, naphthyl group, anthranyl group, phenanthryl group, pyrenyl group, chrysenyl group, fluoranthenyl group and perfluoroaryl groups.
• phenyl group, biphenyl groups, terphenyl group and perfluoroaryl groups are preferable.
• Examples of the arylene group having 6 to 30 carbon atoms include phenylene group, biphenylene group, terphenylene group, naphthylene group, anthranylene group, phenanthrylene group, pyrenylene group, chrysenylene group, fluoranthenylene group and perfluroarylene groups.
• phenylene group, biphenylene group, terphenylene group and perfluoroarylene groups are preferable.
• Examples of the cycloalkylene group having 5 to 30 carbon atoms include cyclopentylene group, cyclohexylene group and cycloheptylene group. Among these groups, cyclohexylene group is preferable.
• heteroaromatic group having 2 to 30 carbon atoms examples include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyradinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group, 6benzofuranyl group, 7
• Examples of the substituent in the group represented by Cz, M or M′ in general formulae (1), (2) and (A) include halogen atoms such as chlorine atom, bromine atom and fluorine atom, carbazole group, hydroxyl group, substituted and unsubstituted amino groups, nitro group, cyano group, silyl group, trifluoromethyl group, carbonyl group, carboxyl group, substituted and unsubstituted alkyl groups, substituted and unsubstituted alkenyl groups, substituted and unsubstituted arylalkyl groups, substituted and unsubstituted aromatic groups, substituted and unsubstituted heteroaromatic heterocyclic groups, substituted and unsubstituted aralkyl groups, substituted and unsubstituted aryloxy groups and substituted and unsubstituted alkyloxyl groups.
• halogen atoms such as chlorine atom, bromine atom and fluorine atom, carb
• fluorine atom methyl group, perfluorophenylene group, phenyl group, naphthyl group, pyridyl group, pyrazyl group, pyrimidyl group, adamantyl group, benzyl group, cyano group and silyl group are preferable.
• the group represented by Cz which is bonded to the group represented by A may be bonded to any of the groups represented by M, L or M′ in general formula (A) representing the group represented by A.
• the bonding mode includes three bonding modes of Cz—M—L—M′, M—L(Cz)—M′ and M—L—M′—Cz.
• the bonding mode includes bonding modes shown in the following:
• Cz represents a substituted or unsubstituted arylcarbazolyl group or carbazolylalkylene group
• M represents a heterocyclic six-membered or seven-membered ring having 4 or 5 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring, a heterocyclic five-membered ring having 2 to 4 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring, a heterocyclic ring having 8 to 11 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring or a substituted or unsubstituted imidazopyridinyl ring, and L represents a substituted or unsubstituted aryl group or arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms.
• Cz represents a substituted or unsubstituted arylcarbazolyl group or carbazolylalkylene group
• M represents a heterocyclic six-membered or seven-membered ring having 4 or 5 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring, a heterocyclic five-membered ring having 2 to 4 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring, a heterocyclic ring having 8 to 11 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring or a substituted or unsubstituted imidazopyridinyl ring, and L represents a substituted or unsubstituted aryl group or arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms.
• Cz represents a substituted or unsubstituted arylcarbazolyl group or carbazolylalkylene group
• M represents a heteroaromatic ring having 2 to 40 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring
• L represents a substituted or unsubstituted aryl group or arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms.
• Cz represents a substituted or unsubstituted arylcarbazolyl group or carbazolylalkylene group
• M and M′ each independently represent a heteroaromatic ring having 2 to 40 carbon atoms and nitrogen atom and forming a substituted or unsubstituted ring, and M and M′ may represent a same ring or different rings, and L represents a substituted or unsubstituted aryl group or arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms or a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms.
• Cz represents a substituted or unsubstituted arylcarbazolyl group and, more preferably, phenylcarbazolyl group. It is preferable that the aryl portion of the arylcarbazolyl group is substituted with carbazolyl group.
• the energy gap of the triplet state of a compound represented by general formula (1) or (2) is 2.5 to 3.3 eV and more preferably 2.5 to 3.2 eV. It is preferable that the energy gap of the singlet state of a compound represented by general formula (1) or (2) is 2.8 to 3.8 eV and more preferably 2.9 to 3.7 eV.
• the organic EL device of the present invention comprises an anode, a cathode and an organic thin film layer comprising at least one layer disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises the material for organic electroluminescence devices comprising the compound represented by the above general formula (1) or (2).
• the organic EL device of the present invention comprises the material for organic electroluminescence devices comprising the compounds represented by the above general formula (1) or (2) in the light emitting layer, the electron transporting layer or the hole transporting layer.
• the organic EL device of the present invention emits bluish light and the purity of color of the emitted light is as excellent as (0.12, 0.10) to (0.17, 0.20). This property is exhibited since the material for organic EL devices comprising the compound represented by general formula (1) or (2) of the present invention has a great energy gap.
• the organic EL device of the present invention emits light by a multiplet excitation which is the excitation to the triplet state or higher.
• the material for organic electroluminescence devices is a host material of the organic EL device.
• the host material is a material into which holes and electrons can be injected and which has the function of transporting holes and electrons and emitting fluorescent light by recombination of holes and electrons.
• the compounds represented by general formulae (1) and (2) in the present invention are useful also as the organic host material for phosphorescence devices since the energy gap of the singlet state is as high as 2.8 to 3.8 eV and the energy gap of the triplet state is as high as 2.5 to 3.3 eV.
• the phosphorescence device is the organic device which comprises a substance emitting light based on the transition from the energy level of the triplet state to the energy level of the ground singlet state with a stronger intensity than those emitted from other substances, i.e., a phosphorescent material such as organometallic complexes comprising at least one metal selected from Groups 7 to 11 of the Periodic Table, and emits light under an electric field utilizing the so-called phosphorescence.
• a phosphorescent material such as organometallic complexes comprising at least one metal selected from Groups 7 to 11 of the Periodic Table
• the singlet exciton and the triplet exciton are mixed in the formed excited molecules and it is said that the ratio of the amount of the singlet exciton to the amount of the triplet exciton is 1:3 and the triplet exciton is formed in a greater amount.
• the exciton contributing to the light emission is the singlet exciton and the triplet exciton does not emit light. Therefore, the triplet exciton is ultimately consumed as heat and the light is emitted by the singlet exciton which is formed in a smaller amount. Therefore, in these organic EL devices, the energy transferred to the triplet exciton in the energy generated by the recombination of holes and electrons causes a great loss.
• an excited triplet state having an energy state higher than the excited triplet state of a phosphorescent organometallic complex comprising a metal selected from the Group 7 to 11 of the Periodic Table is formed; the film having a more stable form is formed; the glass transition temperature is higher (Tg: 80 to 160° C.); the holes and the electrons are efficiently transported; the compound is electrochemically and chemically stable; and the formation of impurities which may work as a trap or causes the loss in the light emission is suppressed during the preparation and the use.
• the organic EL device of the present invention comprises, as described above, one or more organic thin film layers formed between the anode and the cathode.
• a light emitting layer is formed between the anode and the cathode.
• the light emitting layer comprises a light emitting material and, further, a hole injecting material for transporting holes injected from the anode to the light emitting material or an electron injecting material for transporting electrons injected from the cathode to the light emitting material. It is preferable that the light emitting material exhibits a very excellent phosphorescent quantum efficiency, has a great ability of transporting both holes and electrons and forms a uniform thin layer.
• Examples of the organic EL device of the multi-layer type include organic EL device comprising a laminate having a multi-layer construction such as (the anode/the hole injecting layer/the light emitting layer/the cathode), (the anode/the light emitting layer/the electron injecting layer/the cathode) and (the anode/the hole injecting layer/the light emitting layer/the electron injecting layer).
• the light emitting layer in addition to the compound represented by general formula (1) or (2) of the present invention, conventional host materials, light emitting materials, doping materials, hole injecting materials and electron injecting materials and combinations of these materials may be used, where necessary.
• a multi-layer structure for the organic EL device decreases in the luminance and the life due to quenching can be prevented and the luminance of emitted light and the efficiency of light emission can be improved with other doping materials.
• doping materials contributing to the light emission of the phosphorescence in combination, the luminance of emitted light and the efficiency of light emission can be improved in comparison with conventional devices.
• the hole injecting layer, the light emitting layer and the electron injecting layer may each have a multi-layer structure.
• the layer into which holes are injected from the electrode is called the hole injecting layer and the layer which receives holes from the hole injecting layer and transports holes to the light emitting layer is called the hole transporting layer.
• the layer into which electron are injected from the electrode is called the electron injecting layer and the layer which receives electrons from the electron injecting layer and transports electrons to the light emitting layer is called the electron transporting layer.
• the layers are selected in accordance with the energy levels of the material, heat resistance and adhesion with the organic thin film layers or the metal electrodes.
• the electron transporting layer and/or the hole transporting layer may comprise the material for organic EL devices of the present invention which comprises any of the compounds represented by general formulae (1) and (2).
• the hole injecting layer, the electron injecting layer and the hole barrier layer may comprise the material for organic EL devices of the present invention.
• a phosphorescent light emitting compound and the material for organic EL materials of the present invention may be used as a mixture.
• Examples of the light emitting material and the host material which can be used for the organic thin film layer in combination with the compound represented by general formula (1) or (2) include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronen, chrysene, fluoresceine, perylene, phthaloperylene, naphthaloperylene, perynone, phthaloperynone, naphthaloperynone, diphenylbutadiene, tetraphenylbutadiene, coumarine, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, metal complexes of quinoline, metal complexes of aminoquinoline, metal complexes of benzoquinoline, imines, diphenylethylene, vinylanthracene, diaminoanthracene, diaminocarbazole,
• phosphorescent organometallic complexes are preferable since the external quantum efficiency of the device can be improved.
• the metal in the phosphorescent organometallic complex include ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold. It is preferable that the organometallic complex is an organometallic compound represented by the following general formula (3):
• Al represents a substituted or unsubstituted aromatic hydrocarbon cyclic group or aromatic heterocyclic group which is preferably phenyl group, biphenyl group, naphthyl group, anthryl group, thienyl group, pyridyl group, quinolyl group or isoquinolyl group.
• substituents examples include halogen atoms such as fluorine atom; alkyl groups having 1 to 30 carbon atoms such as methyl group and ethyl group; alkenyl groups such as vinyl group; alkoxycarbonyl groups having 1 to 30 carbon atoms such as methoxycarbonyl group and ethoxycarbonyl group; alkoxyl groups having 1 to 30 carbon atoms such as methoxy group and ethoxyl group; aryloxy groups such as phenoxyl group and benzyloxyl group; dialkylamino groups such as dimethylamino group and diethylamino group; acyl groups such as acetyl group; haloalkyl groups such as trifluoromethyl group; and cyano group.
• halogen atoms such as fluorine atom
• alkyl groups having 1 to 30 carbon atoms such as methyl group and ethyl group
• alkenyl groups such as vinyl group
• a 2 represents a substituted or unsubstituted aromatic heterocyclic group having nitrogen atom as the atom forming the heterocyclic ring, which is preferably pyridyl group, pirimidyl group, pyrazine group, triazine group, benzothiazole group, benzoxazole group, benzimidazole group, quinolyl group, isoquinolyl group, quinoxaline group or phenanthridine group.
• substituents described as the examples of the substituent for the group represented by A 1 are examples of the substituent for the group represented by A 1 .
• the ring having the group represented by A 1 and the ring having the group represented by A 2 may form one condensed ring.
• Examples of the condensed ring include 7,8-benzoquinoline group.
• Q represents a metal selected from metals of Groups 7 to 11 of the Periodic Table, which is preferably ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum or gold.
• L represents a bidentate ligand, which is preferably selected from ligands of the ⁇ -diketone type such as acetylacetonates and pyromellitic acid.
• n and n each represent an integer.
• Q represents a divalent metal
• Q represents a trivalent metal
• organometallic complex represented by the above general formula (3) are shown in the following. However, the organometallic complex is not limited to these compounds.
• the hole injecting material compounds which have the ability to transport holes, exhibits the excellent effect of receiving holes injected from the anode and the excellent effect of injecting holes to the light emitting layer or the light emitting material, prevents transfer of excitons formed in the light emitting layer to the electron injecting layer or the electron injecting material and has the excellent ability of forming a thin film, are preferable.
• the hole injecting compound examples include phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxazoles, oxadiazoles, triazoles, imidazoles, imidazolones, imidazolethiones, pyrazolines, pyrazolones, tetrahydroimidazoles, hydrazones, acylhydrazones, polyarylalkanes, stilbene, butadiene, triphenylamine of the benzidine type, triphenylamine of the styrylamine type, triphenylamine of the diamine type, derivatives of the above compounds and macromolecular materials such as polyvinyl-carbazoles, polysilanes and electrically conductive macromolecules.
• the hole injecting material is not limited to these materials.
• the more effective hole injecting materials are aromatic tertiary amine derivatives and phthalocyanine derivatives.
• aromatic tertiary amine derivatives include triphenylamine, tritolylamine, tolyldiphenylamine, N,N′-diphenyl-N,N′-(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine, N,N,N′,N′-(4-methylphenyl)-1,1′-phenyl-4,4′-diamine, N,N,N′,N′-(4-methylphenyl)-1,1′-biphenyl-4,4′-diamine, N,N′-diphenyl-N,N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N,N′-(methylphenyl)-N,N′-(4-n-butylpheny
• the aromatic tertiary amine is not limited to these compounds.
• the phthalocyanine (Pc) derivative include phthalocyanine derivatives and naphthalocyanine derivatives such as H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO)AlPc, (HO)GaPc, VOPc, TiOPc, MoOPc and GaPc—O—GaPc.
• the phthalocyanine derivative is not limited to these compounds.
• the electron injecting material compounds which have the ability to transport electrons, exhibits the excellent effect of receiving electrons injected from the anode and the excellent effect of injecting electrons to the light emitting layer or the light emitting material, prevents transfer of excitons formed in the light emitting layer to the hole injecting layer and has the excellent ability of forming a thin film, are preferable.
• the electron injecting compound examples include fluorenone, anthraquinodimethane, diphenoquinone, thiopyrane dioxide, oxazoles, oxadiazoles, triazoles, imidazoles, perylenetetracarboxylic acid, quinoxaline, fluorenylidenemethane, anthraquinodimethane, anthrone and derivatives of these compounds.
• the electron injecting material is not limited to these compounds.
• the more effective electron injecting materials are metal complex compounds and five-membered derivatives having nitrogen.
• the metal complex compound include 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2methyl-8-hydroxyquinolinato)aluminum, tris(8- hydroxyquinolinato)-gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2- methyl- 8-quinolinato)chlorogallium, bis(2methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato) (1naphtholato)aluminum and bis(2-methyl-8-quinolinato)(2-napht
• the five-membered derivative having nitrogen oxazoles, thiazoles, oxadiazoles, thiadiazoles, triazoles and derivatives of these compounds are preferable.
• the five-membered derivative having nitrogen include bis(1-phenyl)-1,3,4-oxazole, dimethylPOPOP, 2,5bis(1-phenyl)-1,3,4-thiazole, 2,5-bis(1-phenyl)-1,3,4-oxadiazole, 2-(4′-tertbutylphenyl)-5-(4′′-biphenyl)-1,3,5-oxadiazole, 2,5-bis(1-naphthyl)-1,3,4-oxadiazole, 1,4-bis[2-(5-phenyloxadiazolyl)]benzene, 1 ,4-bis [2-(5-phenyloxadiazolyl)-4-tert-butylbenzene], 2-(4′-tert-
• the property of charge injection can be improved by adding an electron-accepting compound to the hole injecting material and an electron-donating compound to the electron injecting material.
• the electrically conductive material used for the anode of the organic EL device of the present invention a material having a work function greater than 4 eV is suitable and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, alloys of these metals, metal oxides such as tin oxides and indium oxide used for ITO substrates and NESA substrates and organic electrically conductive resins such as polythiophene and polypyrrol are used.
• the electrically conductive material used for the cathode a material having a work function smaller than 4 eV is suitable and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum and alloys of these metals are used.
• the electrically conductive material used for the cathode is not limited to these materials.
• Typical examples of the alloy include magnesium/silver, magnesium/indium and lithium/aluminum.
• the alloy is not limited to these alloys.
• the composition of the alloy is controlled by the temperature of the source of vaporization, the atmosphere and the degree of vacuum and a suitable composition is selected.
• the anode and the cathode may be formed with a structure having two or more layers, where necessary.
• the organic EL device of the present invention may comprise an inorganic compound layer between at least one of the electrodes and the above organic thin film layer.
• the inorganic compound used for the inorganic compound layer include various types of oxides, nitrides and oxide nitrides such as alkali metal oxides, alkaline earth metal oxides, rare earth oxides, alkali metal halides, alkaline earth metal halides, rare earth halides, SiO x , AlO x , SiN x , SiON, AlON, GeO x , LiO x , LiON, TiO x , TiON, TaO x , TaON, TaN x and C.
• SiO x , AlO x , SiN x , SiON, AlON, GeO x and C are preferable since a stable interface layer of injection is formed.
• LiF, MgF 2 , CaF 2 and NaF are preferable.
• the organic EL device of the present invention it is preferable that at least one face is sufficiently transparent in the region of the wavelength of the light emitted by the device so that the light emission is achieved efficiently. It is preferable that the substrate is also transparent.
• the conditions in the vapor deposition or the sputtering are set so that the prescribed transparency is surely obtained using the above electrically conductive material. It is preferable that the electrode of the light emitting face has a transmittance of light of 10% or greater.
• the substrate is not particularly limited as long as the substrate has the mechanical and thermal strength and is transparent. Examples of the substrate include glass substrates and transparent films of resins.
• Examples of the transparent film of a resin include films of polyethylene, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, polystyrene, polymethyl methacrylate, polyvinyl chloride, polyvinyl alcohol, polyvinyl butyral, nylon, polyether ether ketones, polysulfones, polyether sulfones, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymers, polyvinyl fluoride, tetrafluoro-ethylene-ethylene copolymers, tetrafluoroethylene-hexafluoropropylene copolymers, polychlorotrifluoroethylene, polyvinylidene fluoride, polyesters, polycarbonates, polyurethanes, polyether imides, polyimides and polypropylene.
• a protective layer is formed on the surface of the device or the entire device is covered with a silicone oil or a resin so that stability to the temperature, the humidity and the atmosphere is improved.
• each layer of the organic EL device of the present invention any of the dry processes of film formation such as the vacuum vapor deposition, the sputtering, the plasma plating and the ion plating and the wet processes of film formation such as the spin coating, the dipping and the flow coating, can be applied.
• the thickness of each film is not particularly limited. However, it is necessary that the thickness of the film be set at a suitable value. When the thickness is excessively great, application of a greater voltage is necessary to obtain the same output of the light and the efficiency of light emission decreases. When the thickness is excessively small, pin holes are formed and sufficient light emission cannot be obtained even when an electric field is applied. In general, a thickness in the range of 5 nm to 10 ⁇ m is suitable and a thickness in the range of 10 nm to 0.2 ⁇ m is preferable.
• the material forming each layer is dissolved or suspended in a suitable solvent such as ethanol, chloroform, tetrahydrofuran and dioxane and a thin film is formed from the obtained solution or suspension. Any of the above solvents can be used.
• suitable resins and additives may be used to improve the property for film formation and to prevent formation of pin holes in the film.
• the resin which can be used examples include insulating resins such as polystyrene, polycarbonates, polyarylates, polyesters, polyamides, polyurethanes, polysulfones, polymethyl methacrylate, polymethyl acrylate, cellulose and copolymers of these resins; photoconductive resins such as poly-N-vinylcarbazole and polysilanes; and electrically conductive resins such as polythiophene and polypyrrol.
• the additive include antioxidants, ultraviolet light absorbents and plasticizers.
• the organic EL device emitting blue light with a high purity of color can be obtained.
• This organic EL device can be advantageously used for a photosensitive member for electronic photograph, a planar light emitting member such as a flat panel display of wall televisions, a back light of copiers, printers and liquid crystal displays, a light source for instruments, a display panel, a marking light and an accessory.
• the lowest excited triplet energy level T1 was measured.
• a tangent was drawn to the increasing line at the short wavelength side of the phosphorescence spectrum and the wavelength at the intersection of the tangent and the abscissa (the end of light emission) was obtained. The obtained wavelength was converted into the energy.
• the excited singlet energy gap was measured. Using a toluene solution (10 ⁇ 5 moles/liter) of a sample, the absorption spectrum was obtained by a spectrometer for absorption of ultraviolet and visible light manufactured by HITACHI Co. Ltd. A tangent was drawn to the increasing line at the long wavelength side of the spectrum and the wavelength at the intersection of the tangent and the abscissa (the end of absorption) was obtained. The obtained wavelength was converted into the energy.
• the formed solid substance was separated by filtration under a reduced pressure and a gray solid substance was obtained.
• the obtained solid substance was recrystallized from benzene and 1.7 g (the yield: 17%) of white crystals were obtained. It was confirmed by 90 MHz 1 H-NMR and FD-MS that the obtained crystals were the target substance (A26).
• the result of the measurement by FD-MS is shown in the following:
• the organic layer was washed with a 5% aqueous solution of hydrochloric acid and water, successively, and dried with anhydrous sodium sulfate. After the organic solvent was removed by distillation, 15 ml of ethyl acetate was added. The formed crystals were separated by filtration and washed with ethyl acetate and 3.5 g (the yield: 83%) of yellowish white crystals were obtained. It was confirmed by 90 MHz 1 H-NMR and FD-MS that the obtained crystals were the target substance (A72). The result of the measurement by FD-MS is shown in he following:
• the organic layer was washed with water and dried with anhydrous sodium sulfate. After the organic solvent was removed by distillation under a reduced pressure, the residue of distillation was suspended into 21 ml of dioxane. To the obtained suspension, 0.12 g (0.6 mmoles) of copper iodide, 2.9 g (14 mmoles) of potassium phosphate and 0.8 ml (6mmoles) of trans-1,2-cyclohexanediamine were added. Under the atmosphere of argon, the resultant mixture was heated for 18 hours under the refluxing condition. The reaction solution was then cooled at the room temperature. Methylene chloride and water were added and the resultant mixture was separated into two layers.
• 1,3,5-Tribromobenzene in an amount of 13.0 g (41 mmoles), 10.0 g (45 mmoles) of 3,5-diphenylpyrazole, 0.8 g (4 mmoles) of copper iodide and 11.9 g (86 mmoles) of potassium carbonate were suspended into 50 ml of 1,4-dioxane.
• 4.9 ml (41 mmoles) of trans-1,2-cyclohexanediamine was added. Under the atmosphere of argon, the resultant mixture was heated for 18 hours under the refluxing condition. The reaction solution was then cooled at the room temperature. Methylene chloride and water were added and the resultant mixture was separated into two layers.
• the organic layer was washed with water and dried with anhydrous sodium sulfate. After the organic solvent was removed by distillation, the residue of distillation was suspended into 15 ml of 1,4-dioxane. To the obtained suspension, 0.08 g (0.4 mmoles) of copper iodide, 2.9 g (14 mmoles) of potassium phosphate and 0.5 ml (4 mmoles) of trans-1,2-cyclohexanediamine were added. Under the atmosphere of argon, the resultant mixture was heated for 14 hours under the refluxing condition. The reaction solution was then cooled at the room temperature. Methylene chloride and water were added and the resultant mixture was separated into two layers.
• the organic layer was washed with water and dried with anhydrous sodium sulfate. After the organic solvent was removed by distillation under a reduced pressure, 5 ml of ethanol and 15 ml of ethyl acetate were added. The formed crystals were separated by filtration and washed with a mixed solvent containing ethyl acetate and ethanol in relative amounts by volume of 5:2 and 2.4 g (the yield: 87%) of yellowish white crystals were obtained. It was confirmed by 90 MHz 1 H—NMR and FD-MS that the obtained crystals were the target substance (A108). The result of the measurement by FD-MS is shown in the following:
• a glass substrate manufactured by GEOMATEC Company of 25 mm ⁇ 75 mm ⁇ 1.1 mm thickness having an ITO transparent electrode was cleaned by application of ultrasonic wave in isopropyl alcohol for 5 minutes and then by exposure to ozone generated by ultraviolet light for 30 minutes.
• the glass substrate having the transparent electrode lines which had been cleaned was attached to a substrate holder of a vacuum vapor deposition apparatus.
• a film of N,N′-bis(N,N′-diphenyl-4-aminophenyl)-N, N′-diphenyl-4,4′-diamino-1,1′-biphenyl (a film of TPD232) having a thickness of 60 nm was formed in a manner such that the formed film covered the transparent electrode.
• the formed film of TPD232 worked as the hole injecting layer.
• a film of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (a film of NPD) having a thickness of 20 nm was formed by vapor deposition.
• the formed film of NPD worked as the hole transporting layer.
• a film of the above Compound (A5) having a thickness of 40 nm was formed by vapor deposition.
• Compound (D1) shown in the following was vapor deposited in an amount such that the ratio of the amounts by weight of Compound (A5) to Compound (D1) was 40:3.
• Compound (D1) is a light emitting compound having a singlet energy as low as 2.79 eV so that blue light is emitted.
• the formed mixed film of Compound (A5) and Compound (D1) worked as the light emitting layer.
• a film of BAlq shown in the following (Me means methyl group) having a thickness of 20 nm was formed.
• the film of BAlq worked as the electron injecting layer.
• Li the source of lithium: manufactured by SAES GETTERS Company
• Alq binary vapor deposited and an Alq:Li film having a thickness of 10 nm was formed as the second electron injecting layer (the cathode).
• metallic aluminum was vapor deposited to form a metal cathode and an organic EL device was prepared.
• a glass substrate (manufactured by GEOMATEC Company) of 25 mm ⁇ 75 mm ⁇ 0.7 mm thickness having an ITO transparent electrode was cleaned by application of ultrasonic wave in isopropyl alcohol for 5 minutes and then by exposure to ozone generated by ultraviolet light for 30 minutes.
• the glass substrate having the transparent electrode lines which had been cleaned was attached to a substrate holder of a vacuum vapor deposition apparatus.
• a film of copper phthalocyanine shown in the following (a film of CuPc) having a thickness of 10 nm was formed in a manner such that the formed film covered the transparent electrode.
• the formed film of CuPc worked as the hole injecting layer.
• a film of 1,1′-bis[4-N,N-di(p-tolyl)aminophenyl]cyclohexane (a film of TPAC) having a thickness of 30 nm was formed.
• the formed film of TPAC worked as the hole transporting layer.
• a film of the above Compound (A72) having a thickness of 30 nm was formed by vapor deposition and the light emitting layer was formed.
• Ir bis[(4,6-difluorophenyl)pyridinato-N,C 2 ′] picolinate (FIrpic shown in the following) as the phosphorescent Ir metal complex was added.
• the concentration of FIrpic in the light emitting layer was set at 7% by weight. This layer worked as the light emitting layer.
• a film of Alq having a thickness of 30 nm was formed on the film formed above.
• the film of Alq worked as the electron injecting layer.
• LiF as the alkali metal halide was vapor deposited in an amount such that the formed film had a thickness of 0.2 nm and, then, aluminum was vapor deposited in an amount such that the formed film had a thickness of 150 nm
• the formed film of Alq:Li film worked as the cathode.
• an organic EL device was prepared.
• the organic EL devices using the compounds of the present invention could be driven at a lower voltage and emit blue light at a higher efficiency. Since the energy gap of the compounds of the present invention is great, light emitting molecules having a great energy gap could be mixed into the light emitting layer and used for the light emission.
• the organic electroluminescence device As described above in detail, by utilizing the material for organic electroluminescence devices comprising the compound represented by general formula (1) or (2) of the present invention, the organic electroluminescence device emitting blue light with a high efficiency of light emission and an excellent purity of color can be obtained. Therefore, the organic electroluminescence device of the present invention is very useful as the light source for various electronic instruments.

Priority Applications (3)

Applications Claiming Priority (4)

Related Child Applications (1)

Publications (1)

Family

ID=28456229

Family Applications (4)

Family Applications After (3)

Country Status (6)

Cited By (92)

Families Citing this family (129)

Citations (1)

Family Cites Families (40)

• 2003
  • 2003-03-19 EP EP03712758A patent/EP1489155A4/fr not_active Withdrawn
  • 2003-03-19 JP JP2003578493A patent/JP4316387B2/ja not_active Expired - Lifetime
  • 2003-03-19 WO PCT/JP2003/003329 patent/WO2003080760A1/fr active Application Filing
  • 2003-03-19 KR KR1020047014947A patent/KR100948700B1/ko active IP Right Review Request
  • 2003-03-19 EP EP08156371.0A patent/EP2169028B1/fr not_active Expired - Lifetime
  • 2003-03-21 TW TW092106356A patent/TWI306890B/zh not_active IP Right Cessation
  • 2003-03-21 TW TW097115521A patent/TW200904942A/zh not_active IP Right Cessation
  • 2003-03-24 US US10/393,988 patent/US20040086745A1/en not_active Abandoned
• 2005
  • 2005-06-13 US US11/150,342 patent/US8580391B2/en active Active
• 2008
  • 2008-11-07 JP JP2008286590A patent/JP5584406B2/ja not_active Expired - Lifetime
• 2012
  • 2012-05-31 US US13/485,111 patent/US20120298975A1/en not_active Abandoned
  • 2012-08-31 US US13/601,300 patent/US8741450B2/en not_active Expired - Lifetime
• 2013
  • 2013-04-18 JP JP2013087646A patent/JP5771644B2/ja not_active Expired - Lifetime

Patent Citations (1)

Also Published As

Similar Documents