WO2010032663A1 - Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage et matériau d'élément électroluminescent organique - Google Patents

Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage et matériau d'élément électroluminescent organique Download PDF

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WO2010032663A1
WO2010032663A1 PCT/JP2009/065716 JP2009065716W WO2010032663A1 WO 2010032663 A1 WO2010032663 A1 WO 2010032663A1 JP 2009065716 W JP2009065716 W JP 2009065716W WO 2010032663 A1 WO2010032663 A1 WO 2010032663A1
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organic
aromatic hydrocarbon
general formulas
ring
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Japanese (ja)
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智寛 押山
栄作 加藤
雅人 西関
大 池水
信也 大津
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コニカミノルタホールディングス株式会社
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    • 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 Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium 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
    • H10K85/30—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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
    • 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
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • 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
    • C09K2211/1018—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
    • C09K2211/18—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
    • 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

Definitions

  • the present invention relates to an organic electroluminescence element, a display device, a lighting device, and an organic electroluminescence element material.
  • ELD electroluminescence display
  • organic EL elements organic electroluminescent elements
  • Inorganic electroluminescent elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements.
  • an organic EL device has a structure in which a light-emitting layer containing a light-emitting compound is sandwiched between a cathode and an anode, and excitons (excitons) are generated by injecting electrons and holes into the light-emitting layer and recombining them.
  • It is an element that emits light by using light emission (fluorescence / phosphorescence) when the exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts. Therefore, it has a wide viewing angle, high visibility, and since it is a thin-film type completely solid element, it has attracted attention from the viewpoints of space saving and portability.
  • a small amount of a phosphor is doped into a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative to achieve improvement in light emission luminance and a longer device lifetime.
  • an element having an organic light-emitting layer in which 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of phosphor is doped to the host compound for example, Japanese Patent Laid-Open No. 63-264692
  • 8-hydroxyquinoline aluminum complex is used as a host compound.
  • an element having an organic light emitting layer doped with a quinacridone dye for example, JP-A-3-255190 is known.
  • the generation ratio of singlet excitons and triplet excitons is 1: 3, and thus the generation probability of luminescent excited species is 25%. Since the efficiency is about 20%, the limit of the external extraction quantum efficiency ( ⁇ ) is set to 5%.
  • the upper limit of the internal quantum efficiency is 100%.
  • the luminous efficiency is four times that of the excited singlet, and there is a possibility that almost the same performance as a cold cathode tube can be obtained. Therefore, it is attracting attention as a lighting application.
  • Ikai et al Uses a hole transporting compound as a host of a phosphorescent compound.
  • M.M. E. Thompson et al. Use various electron transporting materials as a host of phosphorescent compounds, doped with a novel iridium complex.
  • the light emission brightness and light emission efficiency of the light emitting device are greatly improved compared to conventional devices because the emitted light is derived from phosphorescence. There was a problem that it was lower than the conventional element.
  • wavelength shortening introduction of an electron withdrawing group such as a fluorine atom, a trifluoromethyl group, a cyano group or the like into phenylpyridine as a substituent, and picolinic acid or a pyrazabole-based ligand as a ligand. It is known to introduce.
  • an electron withdrawing group such as a fluorine atom, a trifluoromethyl group, a cyano group or the like into phenylpyridine as a substituent, and picolinic acid or a pyrazabole-based ligand as a ligand. It is known to introduce.
  • the emission wavelength of the light-emitting material is shortened to achieve blue, and a high-efficiency device can be achieved.
  • the light-emitting lifetime of the device is greatly deteriorated, so an improvement in the trade-off is required. It was.
  • a metal complex having phenylpyrazole as a ligand is a light emitting material having a short emission wavelength (see, for example, Patent Documents 1 and 2). Furthermore, a metal complex formed from a ligand having a partial structure in which a 6-membered ring is condensed to a 5-membered ring of phenylpyrazole is disclosed (for example, see Patent Documents 3 and 4). There is disclosure of metal complexes having a phenanthridine skeleton. (For example, refer to Patent Documents 5 and 6.)
  • the present invention has been made in view of such problems, and an object of the present invention is to use an organic EL device material that exhibits specific short-wave light emission, exhibits high light emission efficiency, and has a long light emission lifetime.
  • An organic EL element, an illumination device, and a display device are provided.
  • organic EL element material that exhibits high luminous efficiency with short-wave light emission of blue to blue-green, low driving voltage, and long emission life.
  • the light emitting layer includes a partial structure represented by the following general formula (A), (B), (C), or (D)
  • An organic electroluminescence device comprising at least one compound.
  • E1b to E1o and E1q represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and E1a and E1p are different from each other and represent a carbon atom or a nitrogen atom.
  • the skeleton composed of E1a to E1q has a total of 18 ⁇ electrons.
  • R1a to R1i each represents a hydrogen atom or a substituent, and at least two of R1a to R1i represent an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table.
  • the partial structures represented by any one of the general formulas (A), (B), (C), and (D) are represented by the following general formulas (1), (2), (3), or (4), respectively. 2.
  • E1b to E1o and E1q represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and E1a and E1p are different from each other and represent a carbon atom or a nitrogen atom.
  • the skeleton composed of E1a to E1q has a total of 18 ⁇ electrons.
  • R1a to R1i each represents a hydrogen atom or a substituent, but at least one of R1a and R1b is an aromatic hydrocarbon group or an aromatic heterocyclic group, and at least one of R1c to R1f, Alternatively, at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table.
  • 3. 3 The organic electrolysis according to 2 above, wherein the partial structure represented by any one of the general formulas (1) to (4) is represented by any one of the following general formulas (5) to (8): Luminescence element.
  • E1b to E1o and E1q represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom
  • the ring formed by E1a to E1e represents a 5-membered aromatic heterocyclic ring and is formed by E1l to E1p.
  • the ring represents a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle.
  • E1a and E1p are different from each other and represent a carbon atom or a nitrogen atom.
  • R1a to R1i each represents a hydrogen atom or a substituent, but at least one of R1a and R1b is an aromatic hydrocarbon group or an aromatic heterocyclic group, and at least one of R1c to R1f, Alternatively, at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table. ] 4).
  • E1f to E1o and E1q represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom
  • the ring formed by E1f to E1k represents a 5-membered aromatic heterocyclic ring and is formed by E1l to E1q.
  • the ring represents a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle.
  • E1p represents a carbon atom.
  • R1a to R1i each represents a hydrogen atom or a substituent, but at least one of R1a and R1b is an aromatic hydrocarbon group or an aromatic heterocyclic group, and at least one of R1c to R1f, Alternatively, at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table. ] 6). Any one of 1 to 5 above, wherein the partial structure represented by any one of the general formulas (5) to (8) is represented by any one of the following general formulas (13) to (16): 2.
  • E1f to E1o and E1q represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom
  • the ring formed by E1f to E1k represents a 5-membered aromatic heterocyclic ring and is formed by E1l to E1q.
  • the ring represents a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle.
  • E1p represents a carbon atom.
  • R1a to R1i each represents a hydrogen atom or a substituent, but at least one of R1a and R1b is an aromatic hydrocarbon group or an aromatic heterocyclic group, and at least one of R1c to R1f, Alternatively, at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table. ] 7). 7.
  • the organic electroluminescence device as described in 6 above, wherein the partial structure represented by the general formula (13) is represented by the following general formula (17).
  • R1a to R1i each represents a hydrogen atom or a substituent, but at least one of R1a and R1b is an aromatic hydrocarbon group or an aromatic heterocyclic group, and R1c to R1f At least one or at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table.
  • R1a and R1b is an aromatic hydrocarbon group
  • at least one of R1c to R1f is an aromatic hydrocarbon group. 8.
  • the organic electroluminescence device according to any one of 1 to 7 above.
  • R1b is an aromatic hydrocarbon group.
  • the organic layer As a constituent layer, it has an organic layer containing at least one compound containing a partial structure represented by any one of the general formulas (1) to (17), and the organic layer was formed using a wet process 11.
  • the organic electroluminescence device as described in any one of 1 to 10 above, wherein
  • An organic electroluminescent device having at least a light emitting layer sandwiched between an anode and a cathode, comprising at least one compound represented by the following general formula (18):
  • E1l to E1o and E1q represent a carbon atom or a nitrogen atom, and the ring formed by E1l to E1q represents a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocycle.
  • E1p represents a carbon atom.
  • R1a to R1i each represents a hydrogen atom or a substituent, and at least one of R1a and R1b is an aromatic hydrocarbon group or an aromatic heterocyclic group, and at least one of R1c to R1f, Alternatively, at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • n represents 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table. ] 13. 13
  • the organic electroluminescence device according to any one of 1 to 12, wherein M is platinum or iridium.
  • An organic electroluminescence device material comprising a partial structure represented by any one of the general formulas (1) to (17) according to any one of 1 to 7.
  • a display device comprising the organic electroluminescence element as described in any one of 1 to 13 above.
  • An illumination device comprising the organic electroluminescence element according to any one of 1 to 13 above.
  • an organic EL element material useful for an organic EL element is obtained.
  • the organic EL element material By using the organic EL element material, specific short-wave light emission is observed, high luminous efficiency is exhibited, and driving voltage is low. It was possible to provide an organic EL element having a long emission lifetime, and an illumination device and a display device using the element.
  • the structure defined in any one of 1 to 12 above shows an organic electroluminescent element exhibiting high light emission efficiency and having a long emission lifetime, and an illumination device using the element And a display device could be provided.
  • the present inventors have succeeded in molecular design of an organic EL element material useful for the organic electroluminescence element of the present invention.
  • the organic electroluminescence element material of the present invention was observed to emit light with a specific short wave, and the lifetime of the organic electroluminescence element of the present invention could be remarkably improved.
  • the present inventors focused on the organic EL element material used for the light emitting layer of the organic EL element, and in particular, studied various metal complex compounds used as the light emitting dopant.
  • the present inventors have introduced a substituent into the basic skeleton of a metal complex, and thus it is not a conventionally known approach to control the wavelength or improve the lifetime, but to expand the ⁇ -conjugated surface of the condensed ring.
  • Various complexes were studied under the focus of increasing stability.
  • the present inventors have further studied and are shown in the compounds (also referred to as metal complexes) containing partial structures represented by the general formulas (A) to (D) and (1) to (17) according to the present invention.
  • the emission wavelength shift of the light emitting material is small, and a light emitting dopant having a long lifetime at a desired emission wavelength has been successfully developed.
  • transition metal complex compound containing a partial structure represented by any of them can have a plurality of ligands depending on the valence of the transition metal element represented by M. Moreover, you may have a ligand which has a respectively different structure.
  • the ligands are general formulas (A) to (D), (1) to (4), (5) to (8), (9) to (12), (13) to (16). And the part remove
  • the type of ligand in the complex is preferably composed of 1 to 2 types, and more preferably 1 type.
  • Transition metal elements of groups 8 to 10 of the periodic table The metal used for forming the compound (also referred to as a transition metal complex, a metal complex, or a metal complex compound) containing a partial structure represented by any one of the general formulas (A) to (D) according to the present invention is an element. Transition metal elements belonging to Group 8 to 10 of the periodic table (also simply referred to as transition metals) are used, among which iridium and platinum are preferable transition metal elements.
  • transition metal complex compound-containing layer containing a partial structure represented by any one is not particularly limited as long as it is a charge transporting layer (charge transporting layer), but is not limited thereto.
  • An electron blocking layer is preferable, a light emitting layer or an electron blocking layer is more preferable, and a light emitting layer is particularly preferable.
  • the efficiency improvement (high brightness) of the external extraction quantum efficiency of the organic EL element of this invention and the lifetime improvement of a light emission lifetime are achieved. be able to.
  • the constituent layers of the organic EL element of the present invention will be described in detail later.
  • the ring formed by E1a to E1e represents a 5-membered aromatic heterocycle, such as an oxazole ring, thiazole ring, oxadi
  • a 5-membered aromatic heterocycle such as an oxazole ring, thiazole ring, oxadi
  • examples thereof include an azole ring, an oxatriazole ring, an isoxazole ring, a tetrazole ring, a thiadiazole ring, a thiatriazole ring, an isothiazole ring, a thiophene ring, a furan ring, a pyrrole ring, an imidazole ring, a pyrazole ring, and a triazole ring.
  • a pyrazole ring, an imidazole ring, an oxazole ring, and a thiazole ring are preferable, and a pyrazole ring and an imidazole ring are particularly preferable.
  • Each of these rings may further have a substituent described later.
  • the ring formed by E1f to E1k is a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle.
  • Examples of the 6-membered aromatic hydrocarbon ring formed by E1f to E1k include a benzene ring. Furthermore, you may have the substituent mentioned later.
  • Examples of the 5- or 6-membered aromatic heterocycle formed by E1f to E1k include a furan ring, a thiophene ring, an oxazole ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring. Can be mentioned.
  • Each of these rings may further have a substituent described later.
  • the ring formed by E1l to E1q is a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle. These rings are each synonymous with the 6-membered aromatic hydrocarbon ring or 5-membered or 6-membered aromatic heterocycle formed by E1f to E1k.
  • R1a to R1i each represents a hydrogen atom or a substituent, and at least two of R1a to R1i each represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table.
  • the substituents represented by R1a to R1i are each an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group etc.), alkenyl group (eg, vinyl group, Allyl group, etc.), alkynyl group (eg, ethynyl group, propargyl group, etc.), aromatic hydrocarbon ring group (aromatic carbocyclic group, aryl group, etc.), for example, phenyl group, p-chloroph
  • Acyloxy groups for example, acetyloxy group, ethylcarbonyloxy group, butylcarbonyloxy group, octylcarbonyloxy group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.
  • amide groups for example, methylcarbonylamino group, ethylcarbonyl
  • Amino group dimethylcarbonylamino group, propylcarbonylamino group, pentylcarbonylamino group, cyclohexylcarbonylamino group, 2-ethylhexylcarbonyl group Group, octylcarbonylamino group, dodecylcarbonylamino group, phenylcarbonylamino group, naphthylcarbonylamino group, etc.
  • carbamoyl group for example, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, propylamin
  • a plurality of these substituents may be bonded to each other to form a ring, and when a plurality of substituents are present, each substituent may be the same or different, and linked to each other to form a ring. May be formed.
  • the substituent is preferably an alkyl group, an aromatic hydrocarbon ring group, or an aromatic heterocyclic group.
  • the partial structure represented by any of the general formulas (A) to (D) is preferable.
  • Partial structure represented by any one of general formulas (1) to (4) >> The partial structures represented by the general formulas (1) to (4) according to the present invention will be described.
  • the 5-membered aromatic heterocycle formed by E1a to E1e is represented by any one of the general formulas (A) to (D). In the partial structure, it is synonymous with the 5-membered aromatic heterocycle formed by E1a to E1e.
  • the 6-membered aromatic hydrocarbon ring formed by E1l to E1q is any one of the general formulas (A) to (D). In the partial structure represented, it is synonymous with the 6-membered aromatic hydrocarbon ring formed by E1l to E1q.
  • the 5- or 6-membered aromatic heterocycle formed by E1l to E1q is any of the general formulas (A) to (D). Are the same as the 5-membered or 6-membered aromatic heterocycle formed by E1l to E1q.
  • R1a to R1i each represents a hydrogen atom or a substituent, and at least one of R1a and R1b is an aromatic hydrocarbon group, or And at least one of R1c to R1f or at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • R1a and R1b are aromatic hydrocarbon group. It is preferable that at least one of R1c to R1f or at least one of R1g to R1i is an aromatic hydrocarbon group.
  • R1d or R1e is preferably an aromatic hydrocarbon group.
  • R1a to R1i are each a hydrogen atom or a substituent represented by any one of the general formulas (A) to (D)
  • the structure is synonymous with the substituents represented by R1a to R1i.
  • the partial structure represented by the general formula (1) is most preferable.
  • the partial structure represented by any of the above general formulas (1) to (4) is preferable.
  • the 5-membered aromatic heterocycle formed by E1a to E1e is represented by any one of the general formulas (1) to (4). In the partial structure, it is synonymous with the 5-membered aromatic heterocycle formed by E1a to E1e.
  • the 6-membered aromatic hydrocarbon ring formed by E1l to E1q is any one of the general formulas (1) to (4). In the partial structure represented, it is synonymous with the 6-membered aromatic hydrocarbon ring formed by E1l to E1q.
  • the 5-membered or 6-membered aromatic heterocycle formed by E1l to E1q is any of the general formulas (1) to (4). Are the same as the 5-membered or 6-membered aromatic heterocycle formed by E1l to E1q.
  • R1a to R1i each represents a hydrogen atom or a substituent, and at least one of R1a and R1b is an aromatic hydrocarbon group, or And at least one of R1c to R1f or at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • R1a and R1b are aromatic hydrocarbon group. It is preferable that at least one of R1c to R1f or at least one of R1g to R1i is an aromatic hydrocarbon group.
  • R1d or R1e is preferably an aromatic hydrocarbon group.
  • R1a to R1i are each a hydrogen atom or a substituent represented by any one of the general formulas (1) to (4)
  • the structure is synonymous with the substituents represented by R1a to R1i.
  • the partial structure represented by the general formula (5) is most preferable.
  • the partial structure represented by any of the above general formulas (5) to (8) is preferable.
  • the 5-membered aromatic heterocycle formed by E1f to E1k is represented by any one of the general formulas (1) to (4). In the partial structure, it is synonymous with the 5-membered aromatic heterocycle formed by E1a to E1e.
  • the 6-membered aromatic hydrocarbon ring formed by E1l to E1q is any one of the general formulas (1) to (4). In the partial structure represented, it is synonymous with the 6-membered aromatic hydrocarbon ring formed by E1l to E1q.
  • the 5-membered or 6-membered aromatic heterocycle formed by E1l to E1q is any of the general formulas (1) to (4). Are the same as the 5-membered or 6-membered aromatic heterocycle formed by E1l to E1q.
  • R1a to R1i each represents a hydrogen atom or a substituent, and at least one of R1a and R1b is an aromatic hydrocarbon group, or And at least one of R1c to R1f or at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • R1a and R1b are aromatic hydrocarbon group. It is preferable that at least one of R1c to R1f or at least one of R1g to R1i is an aromatic hydrocarbon group.
  • R1d or R1e is preferably an aromatic hydrocarbon group.
  • the partial structure represented by the general formula (9) is most preferable.
  • the substituents represented by R1a to R1i are the partial structures represented by any one of the general formulas (1) to (4). Are the same as the substituents represented by R1a to R1i.
  • the partial structure represented by any of the general formulas (5) to (8) is preferable. It is mentioned as one aspect.
  • the 5-membered aromatic heterocycle formed by E1f to E1k is represented by any one of the general formulas (1) to (4). In the partial structure, it is synonymous with the 5-membered aromatic heterocycle formed by E1a to E1e.
  • the 6-membered aromatic hydrocarbon ring formed by E1l to E1q is any one of the general formulas (1) to (4). In the partial structure represented, it is synonymous with the 6-membered aromatic hydrocarbon ring formed by E1l to E1q.
  • the 5-membered or 6-membered aromatic heterocycle formed by E1l to E1q is any of the general formulas (1) to (4). Are the same as the 5-membered or 6-membered aromatic heterocycle formed by E1l to E1q.
  • R1a to R1i each represents a hydrogen atom or a substituent, and at least one of R1a and R1b is an aromatic hydrocarbon group, or And at least one of R1c to R1f or at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • R1a and R1b are aromatic hydrocarbon group. It is preferable that at least one of R1c to R1f or at least one of R1g to R1i is an aromatic hydrocarbon group.
  • R1d or R1e is preferably an aromatic hydrocarbon group.
  • the substituents represented by R1a to R1i are the partial structures represented by any one of the general formulas (1) to (4). Are the same as the substituents represented by R1a to R1i.
  • the partial structure represented by the general formula (13) is preferable.
  • the partial structure represented by the general formula (17) is most preferable.
  • R1a to R1i each represents a hydrogen atom or a substituent, and at least one of R1a and R1b is an aromatic hydrocarbon group or an aromatic heterocyclic group. And at least one of R1c to R1f or at least one of R1g to R1i represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • R1a and R1b are aromatic hydrocarbon group. It is preferable that at least one of R1c to R1f or at least one of R1g to R1i is an aromatic hydrocarbon group.
  • R1d or R1e is preferably an aromatic hydrocarbon group.
  • the substituents represented by R1a to R1i have the same meanings as the substituents represented by R1a to R1i in the partial structure represented by the general formula (17). It is.
  • At least one of R1a and R1b is an aromatic hydrocarbon group or an aromatic heterocyclic group
  • at least one of R1c to R1f is The case where it is an aromatic hydrocarbon group or an aromatic heterocyclic group is preferable.
  • At least one of R1a and R1b is an aromatic hydrocarbon group, and at least one of R1c to R1f is an aromatic hydrocarbon group Is preferred.
  • the compound according to the present invention is preferably a compound represented by the general formula (18).
  • the 6-membered aromatic hydrocarbon ring or 6-membered aromatic heterocycle formed by E1l to E1q is formed of E1l to E1q in the partial structure represented by any one of the general formulas (1) to (4) The 6-membered aromatic hydrocarbon ring or the 6-membered aromatic heterocycle.
  • the substituents represented by R1a to R1i have the same meaning as the substituents represented by R1a to R1i in the partial structure represented by the general formula (17).
  • at least one of R1a and R1b is an aromatic hydrocarbon group or an aromatic heterocyclic group
  • One represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • n represents 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table.
  • Synthesis Example 1 Synthesis of Exemplified Compound (DA2) >>: Synthesis Example of Organic EL Element Material of the Present Invention An exemplified compound (DA2) which is an organic EL element material of the present invention was synthesized by the steps shown below.
  • reaction mixture was cooled to room temperature, filtered, thoroughly washed with methanol and dried to obtain 0.5 g of ⁇ complex (2).
  • Step 5 Synthesis of acac complex (3)
  • ⁇ complex (2) 0.5 g of ⁇ complex (2), 0.1 g of acetylacetone, 0.1 g of sodium carbonate and 20 ml of 2-ethoxyethanol were introduced, and nitrogen was blown into the flask.
  • a tube, a thermometer and a condenser were attached and set on an oil bath stirrer.
  • the reaction was performed for 2 hours at an internal temperature of about 90 ° C. under nitrogen flow.
  • reaction mixture was cooled to room temperature and the crystals were filtered.
  • the crystals were washed with 30 ml of water and 10 ml of MeOH and dried to obtain 0.4 g of acac complex (3).
  • reaction mixture was cooled to room temperature and the crystals were filtered.
  • the blue light emitting layer preferably has an emission maximum wavelength of 430 nm to 480 nm
  • the green light emitting layer has an emission maximum wavelength of 510 nm to 550 nm
  • the red light emitting layer is preferably a monochromatic light
  • a white light emitting layer may be formed by laminating at least three light emitting layers. Further, a non-light emitting intermediate layer may be provided between the light emitting layers.
  • the organic EL element of the present invention is preferably a white light emitting layer, and is preferably a lighting device using these.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.
  • the total film thickness of the light emitting layer is not particularly limited, but from the viewpoint of improving the uniformity of the film, preventing unnecessary application of high voltage during light emission, and improving the stability of the emission color with respect to the drive current. It is preferable to adjust in the range of 2 nm to 5 ⁇ m, more preferably in the range of 2 nm to 200 nm, and particularly preferably in the range of 10 nm to 20 nm.
  • a light-emitting dopant or a host compound which will be described later, is formed by a known thinning method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink-jet method. it can.
  • the light emitting layer of the organic EL device of the present invention preferably contains a light emitting host compound and at least one kind of light emitting dopant (such as a phosphorescent dopant (also referred to as a phosphorescent dopant) or a fluorescent dopant).
  • a light emitting host compound such as a phosphorescent dopant (also referred to as a phosphorescent dopant) or a fluorescent dopant).
  • the host compound in the present invention is a phosphorescent quantum yield of phosphorescence emission at a room temperature (25 ° C.) having a mass ratio of 20% or more in the compound contained in the light emitting layer. Is defined as a compound of less than 0.1.
  • the phosphorescence quantum yield is preferably less than 0.01.
  • the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.
  • known host compounds may be used alone or in combination of two or more.
  • the organic EL element can be made highly efficient.
  • the light emitting host used in the present invention may be a conventionally known low molecular compound or a high molecular compound having a repeating unit, and a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (deposition polymerization property). Light emitting host).
  • a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
  • Luminescent dopant The light emitting dopant according to the present invention will be described.
  • a fluorescent dopant also referred to as a fluorescent compound
  • a phosphorescent dopant also referred to as a phosphorescent emitter, a phosphorescent compound, a phosphorescent compound, or the like
  • the light emitting dopant used in the light emitting layer or the light emitting unit of the organic EL device of the present invention (sometimes simply referred to as a light emitting material) contains the above host compound. At the same time, it is preferable to contain a phosphorescent dopant.
  • the phosphorescent dopant according to the present invention is a compound in which light emission from an excited triplet is observed.
  • the phosphorescent dopant is a compound that emits phosphorescence at room temperature (25 ° C.) and has a phosphorescence quantum yield of 25. Although it is defined as a compound of 0.01 or more at ° C., a preferable phosphorescence quantum yield is 0.1 or more.
  • the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence dopant according to the present invention achieves the phosphorescence quantum yield (0.01 or more) in any solvent. That's fine.
  • the energy transfer type that obtains light emission from the phosphorescent dopant, and the other is that the phosphorescent dopant becomes a carrier trap, carrier recombination occurs on the phosphorescent dopant, and light emission from the phosphorescent dopant is obtained.
  • the excited state energy of the phosphorescent dopant is required to be lower than the excited state energy of the host compound.
  • the phosphorescent dopant can be appropriately selected from known materials used for the light emitting layer of the organic EL element.
  • the phosphorescent dopant according to the present invention is preferably a complex compound containing a group 8-10 metal in the periodic table of elements, more preferably an iridium compound, an osmium compound, or a platinum compound (platinum complex compound), Among the rare earth complexes, iridium compounds are most preferred.
  • Examples of the compound used as the phosphorescent dopant according to the present invention include the partial structure represented by any one of the general formulas (1) to (4) according to the present invention and any one of the general formulas (5) to (8). Or a transition metal comprising a partial structure represented by any one of the general formulas (9) to (12) or a partial structure represented by any one of the general formulas (13) to (16) Complex compounds are preferred.
  • Fluorescent dopants include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes Examples thereof include dyes, stilbene dyes, polythiophene dyes, and rare earth complex phosphors.
  • Injection layer electron injection layer, hole injection layer >> The injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, it exists between the anode and the light emitting layer or the hole transport layer and between the cathode and the light emitting layer or the electron transport layer. May be.
  • An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance.
  • Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • anode buffer layer hole injection layer
  • copper phthalocyanine is used.
  • examples thereof include a phthalocyanine buffer layer represented by an oxide, an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.
  • cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc.
  • Metal buffer layer typified by lithium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide, etc.
  • the buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m, although it depends on the material.
  • ⁇ Blocking layer hole blocking layer, electron blocking layer>
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on November 30, 1998)” on page 237. There is a hole blocking (hole blocking) layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the structure of the electron transport layer described later can be used as a hole blocking layer according to the present invention, if necessary.
  • the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
  • the carbazole derivative, carboline derivative, or diazacarbazole derivative (shown in which any one of the carbon atoms constituting the carboline ring of the carboline derivative is replaced by a nitrogen atom) is used for the hole blocking layer. It is preferable to contain.
  • the light emitting layer having the shortest wavelength of light emission is preferably closest to the anode among all the light emitting layers.
  • 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.
  • the ionization potential is defined by the energy required to emit electrons at the HOMO (highest occupied molecular orbital) level of the compound to the vacuum level, and can be obtained by the following method, for example.
  • Gaussian 03 Gaussian 03, Revision D.02, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2004.
  • the ionization potential can be obtained by rounding off the second decimal place of the value (eV unit converted value) calculated by performing structural optimization using / 6-31G *.
  • the reason why this calculated value is effective is that there is a high correlation between the calculated value obtained by this method and the experimental value.
  • the ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy.
  • a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd. or a method known as ultraviolet photoelectron spectroscopy can be suitably used.
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved.
  • the structure of the hole transport layer described later can be used as an electron blocking layer as necessary.
  • the film thickness of the hole blocking layer and the electron transport layer according to the present invention is preferably 3 nm to 100 nm, and more preferably 5 nm to 30 nm.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives
  • Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • the above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminoph
  • No. 5,061,569 Having a condensed aromatic ring of, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), JP-A-4-308 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type ( MTDATA) and the like.
  • NPD 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • JP-A-4-308 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type ( MTDATA) and the
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
  • JP-A-11-251067 J. Org. Huang et. al.
  • a so-called p-type hole transport material described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used.
  • these materials are preferably used because a light-emitting element with higher efficiency can be obtained.
  • the hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can.
  • the thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the hole transport layer may have a single layer structure composed of one or more of the above materials.
  • a hole transport layer having a high p property doped with impurities examples thereof include JP-A-4-297076, JP-A-2000-196140, JP-A-2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
  • a hole transport layer having such a high p property because a device with lower power consumption can be produced.
  • the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • the electron transport layer can be provided as a single layer or a plurality of layers.
  • an electron transport material also serving as a hole blocking material used for an electron transport layer adjacent to the light emitting layer on the cathode side is injected from the cathode.
  • any material can be selected and used from among conventionally known compounds. For example, nitro-substituted fluorene derivatives, diphenylquinone derivatives Thiopyrandioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum, Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc.
  • the central metals of these metal complexes are In, Mg, Cu , Ca, Sn, Ga, or Pb can also be used as an electron transport material.
  • metal-free or metal phthalocyanine or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
  • the distyrylpyrazine derivative exemplified as the material for the light emitting layer can also be used as an electron transport material, and an inorganic semiconductor such as n-type-Si, n-type-SiC, etc. as in the case of the hole injection layer and the hole transport layer. Can also be used as an electron transporting material.
  • the electron transport layer can be formed by thinning the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • the thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the electron transport layer may have a single layer structure composed of one or more of the above materials.
  • an electron transport layer having a high n property doped with impurities examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. Appl. Phys. 95, 5773 (2004), and the like.
  • an electron transport layer having such a high n property because an element with lower power consumption can be produced.
  • an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not so high (about 100 ⁇ m or more)
  • a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • a wet film forming method such as a printing method or a coating method can be used.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 nm to 1000 nm, preferably 10 nm to 200 nm.
  • cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 nm to 200 nm.
  • the light emission luminance is improved, which is convenient.
  • a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a film thickness of 1 nm to 20 nm. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
  • a support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. May be opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.
  • polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfone , Polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylates, cyclone resins such as Arton (trade name, manufactured by JSR) or Appel (trade
  • an inorganic film, an organic film or a hybrid film of both may be formed on the surface of the resin film.
  • the water vapor permeability (25 ⁇ 0.5 ° C.) measured by a method according to JIS K 7129-1992. , Relative humidity (90 ⁇ 2)% RH) is preferably 0.01 g / (m 2 ⁇ 24 h) or less, and further, oxygen measured by a method according to JIS K 7126-1987.
  • a high barrier film having a permeability of 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less and a water vapor permeability of 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less is preferable.
  • the material for forming the barrier film may be any material that has a function of suppressing the intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
  • the method for forming the barrier film is not particularly limited.
  • the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, and the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.
  • the opaque support substrate examples include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
  • the external extraction efficiency at room temperature of light emission of the organic EL element of the present invention is preferably 1% or more, more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element ⁇ 100.
  • a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination.
  • the ⁇ max of light emission of the organic EL element is preferably 480 nm or less.
  • ⁇ Sealing> As a sealing means used for this invention, the method of adhere
  • the sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Further, transparency and electrical insulation are not particularly limited.
  • Specific examples include a glass plate, a polymer plate / film, and a metal plate / film.
  • the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
  • the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
  • a polymer film and a metal film can be preferably used because the element can be thinned.
  • the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 ⁇ 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less, and a method according to JIS K 7129-1992. It is preferable that the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) measured in (1) is 1 ⁇ 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less.
  • sealing member For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.
  • the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant may be dispersed in the adhesive.
  • Application of the adhesive to the sealing portion may be performed using a commercially available dispenser or may be printed like screen printing.
  • the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
  • the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
  • vacuum deposition sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma
  • a polymerization method a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil
  • a vacuum is also possible.
  • a hygroscopic compound can also be enclosed inside.
  • Examples of the hygroscopic compound include metal oxides (eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide), sulfates (eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate). Etc.), metal halides (eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.), perchloric acids (eg perchloric acid) Barium, magnesium perchlorate, and the like), and anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
  • metal oxides eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
  • sulfates eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt
  • a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the support substrate with the organic layer interposed therebetween or on the sealing film.
  • the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, and the like used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
  • the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light is totally reflected between the light and the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the direction of the element side surface.
  • a method of improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate and preventing total reflection at the transparent substrate and the air interface (US Pat. No. 4,774,435), A method for improving efficiency by giving light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on the side surface of an element (Japanese Patent Laid-Open No. 1-220394), and light emission from the substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the bodies (Japanese Patent Laid-Open No.
  • these methods can be used in combination with the organic EL device of the present invention.
  • a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • the low refractive index layer examples include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.
  • the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.
  • the method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.
  • This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
  • Light that cannot be emitted due to total internal reflection between layers is diffracted by introducing a diffraction grating in any layer or medium (in a transparent substrate or transparent electrode), and the light is removed. I want to take it out.
  • the diffraction grating to be introduced has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much.
  • the refractive index distribution a two-dimensional distribution
  • the light traveling in all directions is diffracted, and the light extraction efficiency is increased.
  • the position where the diffraction grating is introduced may be in any of the layers or in the medium (in the transparent substrate or the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.
  • the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction grating is preferably two-dimensionally repeated such as a square lattice, a triangular lattice, or a honeycomb lattice.
  • the organic EL device of the present invention is processed on the light extraction side of the substrate so as to provide, for example, a microlens array structure, or combined with a so-called condensing sheet, for example, with respect to a specific direction, for example, the light emitting surface By condensing in the front direction, the luminance in a specific direction can be increased.
  • quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably 10 ⁇ m to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
  • the condensing sheet it is possible to use, for example, a sheet that has been put to practical use in an LED backlight of a liquid crystal display device.
  • a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • BEF brightness enhancement film
  • the shape of the prism sheet for example, the base material may be formed by forming a ⁇ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.
  • a light diffusion plate / film may be used in combination with the light collecting sheet.
  • a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
  • a desired electrode material for example, a thin film made of an anode material is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm.
  • organic compound thin films such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer, which are organic EL element materials, are formed thereon.
  • a method for forming each of these layers there are a vapor deposition method, a wet process (spin coating method, casting method, ink jet method, printing method) and the like as described above, but it is easy to obtain a homogeneous film and it is difficult to generate pinholes.
  • film formation by a coating method such as a spin coating method, an ink jet method, or a printing method is preferable in the present invention.
  • liquid medium for dissolving or dispersing the organic EL material according to the present invention examples include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene.
  • Aromatic hydrocarbons such as cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, and organic solvents such as DMF and DMSO can be used.
  • a dispersion method it can disperse
  • a thin film made of a cathode material is formed thereon by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 50 nm to 200 nm.
  • a desired organic EL element can be obtained.
  • a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode.
  • An alternating voltage may be applied.
  • the alternating current waveform to be applied may be arbitrary.
  • the organic EL element of the present invention can be used as a display device, a display, and various light emission sources.
  • lighting devices home lighting, interior lighting
  • clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light
  • the light source of a sensor etc. are mentioned, It is not limited to this, Especially, it can use effectively for the use as a backlight of a liquid crystal display device, and a light source for illumination.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like during film formation, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned.
  • a conventionally known method is used. Can do.
  • the light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with a total CS-1000 (manufactured by Konica Minolta Sensing) is applied to the CIE chromaticity coordinates.
  • Example 1 Production of Organic EL Element 1-1 >> Transparent support provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm as an anode The substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a substrate NH45 manufactured by NH Techno Glass Co., Ltd.
  • ITO indium tin oxide
  • This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus. Meanwhile, 200 mg of ⁇ -NPD was put into a molybdenum resistance heating boat, and 200 mg of H-1 as a host compound was put into another molybdenum resistance heating boat. 200 mg of BAlq was put into another resistance heating boat made of molybdenum, 100 mg of Comparative 1 was put into another resistance heating boat made of molybdenum, and 200 mg of Alq 3 was put into another resistance heating boat made of molybdenum, and attached to a vacuum deposition apparatus.
  • the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing ⁇ -NPD, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / sec.
  • the hole transport layer was provided.
  • the heating boat containing H-1 and Comparison 1 was energized and heated, and co-deposited on the hole transport layer at a deposition rate of 0.2 nm / second and 0.012 nm / second, respectively.
  • a 40 nm light emitting layer was provided.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the heating boat containing BAlq was energized and heated, and was deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a 10 nm thick hole blocking layer.
  • the heating boat containing Alq 3 is further energized and heated, and deposited on the hole blocking layer at a deposition rate of 0.1 nm / second to further provide an electron transport layer having a thickness of 40 nm. It was.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride 0.5 nm and aluminum 110 nm were vapor-deposited to form a cathode, and an organic EL element 1-1 was produced.
  • FIG. 3 is a schematic diagram of the lighting device, and the organic EL element 101 is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is performed in a nitrogen atmosphere without bringing the organic EL element 101 into contact with the atmosphere. (In a high purity nitrogen gas atmosphere with a purity of 99.999% or more).
  • FIG. 4 shows a cross-sectional view of the lighting device.
  • 105 denotes a cathode
  • 106 denotes an organic EL layer
  • 107 denotes a glass substrate with a transparent electrode.
  • the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
  • the external extraction quantum efficiency was expressed as a relative value with the organic EL element 1-1 as 100.
  • the 50 ° C. driving life was evaluated according to the measurement method shown below.
  • Each organic EL element is driven at a constant current with a current that gives an initial luminance of 1000 cd / m 2 under a constant condition of 50 ° C., and a time that is 1 ⁇ 2 of the initial luminance (500 cd / m 2 ) is obtained.
  • the 50 ° C. drive life is expressed as a relative value when the comparative organic EL element 1-1 is taken as 100.
  • the organic EL device was visually evaluated for the luminescent color when the organic EL device was continuously lit under a constant current condition of 2.5 mA / cm 2 at room temperature. The obtained results are shown in Table 1.
  • the lifetime measurement results in Table 1 are expressed as relative values when the organic EL element 1-1 is taken as 100.
  • the film was co-evaporated on the hole transport layer at a deposition rate of 0.2 nm / second and 0.024 nm / second compared with H-1 to obtain a film thickness of 40 nm.
  • the organic EL device 1-1A of the present invention was produced in the same manner except that the above light emitting layer was provided.
  • organic EL elements 1-2A to 1-37A were respectively produced in the same manner in the production of the light emitting layers of the organic EL elements 1-2 to 1-37.
  • the obtained organic EL device was subjected to continuous lighting under a constant current condition of 2.5 mA / cm 2 at room temperature using CS-1000 (manufactured by Konica Minolta Sensing) as the CIE chromaticity of the device. Coordinates were measured.
  • the CIE chromaticity coordinates of the organic EL element 1-1 are represented by (x1, y1), and the CIE chromaticity coordinates of the organic EL element 1-1A are represented. , (X2, y2), the DC value was obtained using the following formula (1).
  • the organic EL device of the present invention has a high external extraction quantum efficiency, a small deterioration in lifetime under high temperature, and a luminescent color depending on the mixing ratio of the host and the dopant. It is clear that there is no deviation.
  • Example 2 ⁇ Production of full-color display device> (Production of blue light emitting element)
  • the organic EL device 1-5 of Example 1 was used as a blue light emitting device.
  • a green light emitting device was produced in the same manner as in the organic EL device 1-1 of Example 1, except that Comparative 1 was changed to Ir-1, and this was used as the green light emitting device.
  • a red light emitting device was produced in the same manner as in the organic EL device 1-1 of Example 1 except that Comparative 1 was changed to Ir-9, and this was used as a red light emitting device.
  • the red, green, and blue light emitting organic EL elements produced above were juxtaposed on the same substrate to produce an active matrix type full color display device having a configuration as shown in FIG. In FIG. 2, only the schematic diagram of the display part A of the produced display device is shown.
  • a plurality of pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.) juxtaposed with a wiring portion including a plurality of scanning lines 5 and data lines 6 on the same substrate.
  • the scanning lines 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a lattice shape and are connected to the pixels 3 at the orthogonal positions (for details, see FIG. Not shown).
  • the plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5.
  • the image data signal is received from the data line 6 and light is emitted according to the received image data. In this way, a full color display device was produced by appropriately juxtaposing red, green, and blue pixels.
  • Example 3 Production of White Light Emitting Element and White Lighting Device-2 >> This ITO transparent electrode was provided after patterning was performed on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate as an anode.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • the substrate was transferred to a nitrogen atmosphere, and a solution of 50 mg of compound A dissolved in 10 ml of toluene was formed on the first hole transport layer by spin coating at 1000 rpm for 30 seconds. After irradiating with ultraviolet light for 180 seconds to carry out photopolymerization / crosslinking, vacuum drying was performed at 60 ° C. for 1 hour to form a second hole transport layer.
  • this substrate was fixed to a substrate holder of a vacuum vapor deposition apparatus, and 200 mg of Alq 3 was put into a molybdenum resistance heating boat and attached to the vacuum vapor deposition apparatus.
  • the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa, and then heated by energizing the heating boat containing Alq 3 , and deposited on the hole blocking layer at a deposition rate of 0.1 nm / second.
  • An electron transport layer having a thickness of 40 nm was provided.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • Example 4 Preparation of organic EL element 4-1 >> This ITO transparent electrode was provided after patterning was performed on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate as an anode.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing BAlq, and deposited on the electron transport layer at a deposition rate of 0.1 nm / second.
  • a 40 nm electron transport layer was provided.
  • the substrate temperature at the time of vapor deposition was room temperature. Then, 0.5 nm of lithium fluoride and 110 nm of aluminum were vapor-deposited, the cathode was formed, and the light emitting organic EL element was produced.
  • FIG. 3 is a schematic diagram of the lighting device, and the organic EL element 101 is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is performed in a nitrogen atmosphere without bringing the organic EL element 101 into contact with the atmosphere.
  • 4 shows a cross-sectional view of the lighting device.
  • reference numeral 105 denotes a cathode
  • 106 denotes an organic EL layer
  • 107 denotes a glass substrate with a transparent electrode.
  • the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
  • the half-life was expressed as a relative value when the comparative organic EL element 4-1 was set to 100.
  • the organic EL device of the present invention has higher efficiency (external extraction quantum efficiency), longer half-life, and no dark spots compared to the comparative device.

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Abstract

L'invention porte sur un matériau d'élément électroluminescent organique dans lequel une lumière émise à courte longueur d'onde spécifique est visible, qui présente un rendement d'émission de lumière élevé et qui possède une longue durée de vie d'émission, ainsi que sur un élément électroluminescent organique, un dispositif d'éclairage et un dispositif d'affichage utilisant le matériau. L'élément électroluminescent organique comprend au moins une couche émettrice de lumière prise en sandwich entre une anode et une cathode et est caractérisé en ce que la couche émettrice de lumière contient au moins un composé qui contient une structure partielle représentée par la formule générale (A), (B), (C) ou (D).
PCT/JP2009/065716 2008-09-17 2009-09-09 Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage et matériau d'élément électroluminescent organique WO2010032663A1 (fr)

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