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WO2008035664A1 - Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, dispositif d'affichage et d'éclairage - Google Patents

Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, dispositif d'affichage et d'éclairage Download PDF

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WO2008035664A1
WO2008035664A1 PCT/JP2007/068063 JP2007068063W WO2008035664A1 WO 2008035664 A1 WO2008035664 A1 WO 2008035664A1 JP 2007068063 W JP2007068063 W JP 2007068063W WO 2008035664 A1 WO2008035664 A1 WO 2008035664A1
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group
organic
ring
layer
light
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Japanese (ja)
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Masato Nishizeki
Noboru Sekine
Dai Ikemizu
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Konica Minolta Holdings, Inc.
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Priority to JP2008535350A priority Critical patent/JP5644050B2/ja
Publication of WO2008035664A1 publication Critical patent/WO2008035664A1/fr

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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
    • 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
    • C07F15/0086—Platinum compounds
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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    • 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
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    • 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
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
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    • 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
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    • 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

Definitions

  • Organic-elect mouth luminescence element material organic-elect-mouth luminescence element, display device and lighting device
  • the present invention relates to an organic electoluminescence device material, an organic electroluminescence device, a display device, and a lighting device.
  • ELD components include inorganic-electric luminescence elements and organic-electric luminescence elements (hereinafter also referred to as organic EL elements! /).
  • Inorganic electoric luminescence elements require high alternating current voltage to drive the force light-emitting elements that have been used as planar light sources.
  • An organic EL device has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and electrons and holes are injected into the light emitting layer and recombined to generate excitons.
  • a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative is doped with a trace amount of a phosphor to improve emission luminance and extend the lifetime of the element.
  • an element having an organic light emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of phosphor is doped to the host compound for example, JP-A 63-264692
  • an 8-hydroxyquinoline aluminum complex is used as a host
  • an element having an organic light emitting layer doped with a quinacridone dye for example, Japanese Patent Publication No. 3-255190
  • the upper limit of the internal quantum efficiency is 100%, so that in principle the luminous efficiency is four times that of the excited singlet, and almost the same performance as a cold cathode tube is obtained. It is also attracting attention as a lighting application.
  • an electron-withdrawing group such as a fluorine atom, a trifluoromethyl group, and a cyano group has been introduced into phenylpyridine as a substituent, and a picolinic acid villaza ball type as a ligand.
  • the force S which is known to introduce sub-ligands, allows the emission wavelength of the light-emitting material to be shortened to achieve blue color and achieve a highly efficient device. Since it deteriorated significantly, there was a need to improve the trade-off.
  • Patent Document 1 International Publication No. 04/085450 Pamphlet
  • Patent Document 2 JP 2005-53912 A
  • Patent Document 3 International Publication No. 05/007767 Pamphlet
  • Patent Document 4 Pamphlet of International Publication No. 06/046980
  • Patent Document 5 Japanese Patent Application Laid-Open No. 2002-332291
  • Patent Document 6 Japanese Unexamined Patent Application Publication No. 2004-67658
  • Patent Document 7 International Publication No. 04/111066 Pamphlet
  • the present invention has been made in view of the above problems, and an object of the present invention is to provide an organic EL element material having a controlled emission wavelength, high emission efficiency, and a long emission lifetime. It is. In particular, it is to provide an organic EL element material that exhibits high luminous efficiency and has a long light emission lifetime with blue to blue-green short-wave light emission. Furthermore, an organic EL element, a display device, and a lighting device using the same are provided.
  • An organic electoluminescence device material characterized by being a metal complex represented by the following general formula (1).
  • X represents R—N, 0, S, Se or Te.
  • R represents a substituted or unsubstituted alkyl group
  • Y, Y and Y are R—N
  • R represents a substituted, unsubstituted alkyl group, a cycloalkyl group, an aryl group or an aromatic heterocyclic group.
  • R is a hydrogen atom or a substituent
  • G represents a substituent, and n represents 0, 1 or 2.
  • X—L—X is a bidentate ligand
  • X and X each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L is X, X
  • the central metal M is in the periodic table
  • 1 represents a group 1 metal.
  • ml represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • ml + m2 is 2 or 3, which is the same number as the positive charge of the central metal.
  • X represents R—N, 0, S, Se or Te.
  • R represents a substituted, unsubstituted alkyl group
  • Y and Y represent R—N, N or R—C, and N—C ⁇ N together with imidazole ring, triazole ring, tetrazole ring
  • R represents a substituted, unsubstituted alkyl group, cycloanolalkyl group, aryl group or aromatic heterocyclic group.
  • R is a hydrogen atom or a substituent
  • G represents a substituent, and n represents 0, 1 or 2.
  • X—L —X represents a bidentate ligand
  • X and X each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L is X, X and
  • 1 represents a group 1 metal.
  • ml represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • ml + m2 is 2 or 3, which is the same number as the positive charge of the central metal.
  • R represents a substituted or unsubstituted alkyl group
  • R represents a substituted, unsubstituted alkyl group, cycloalkyl group, aryl group or aromatic heterocyclic group.
  • G represents a substituent, and n represents 0, 1 or 2.
  • X—L—X represents a bidentate ligand, and X and X are each
  • L is X, X and bidentate ligand
  • the central metal, M is 8 ⁇ in the periodic table; 1 Group 1 gold
  • ml represents an integer of 1, 2 or 3
  • m2 represents a force m representing an integer of 0, 1 or 2 m l + m2 is 2 or 3, which is the same number as the positive charge of the central metal.
  • R is 2,6-dimethylphenyl group, mesityl group (2,4,6-trimethylphenyl group), tetramethylphenyl group. 5.
  • the center metal M is platinum
  • An organic electoluminescence device comprising the organic electroluminescence device material according to item 1, wherein any one of 1 to 9 is used.
  • the light-emitting layer has a ring structure in which at least one carbon atom of a hydrocarbon ring constituting a force rubazole ring or a force rubazole ring of the carbazolone derivative is substituted with a nitrogen atom as a host compound. 10.
  • the organic electoluminescence device according to any one of 10 to 12 above, comprising a body.
  • a display device comprising the organic electoluminescence device according to any one of 10 to 13.
  • An illuminating device comprising the organic-electric-luminescence element according to any one of 10 to 13.
  • an organic EL element material useful for an organic EL element can be obtained.
  • the emission wavelength is controlled, the emission efficiency is high, and the emission lifetime is long.
  • FIG. 1 is an emission spectrum of the metal complex (Compound 4) of the present invention.
  • FIG. 2 is an emission spectrum of the metal complex (Compound 4) of the present invention.
  • FIG. 3 is an emission spectrum of the metal complex (Compound 14) of the present invention.
  • FIG. 4 is an emission spectrum of the metal complex (Compound 14) of the present invention.
  • FIG. 5 is an emission spectrum of the metal complex of the present invention (Compound 27).
  • FIG. 6 is an emission spectrum of the metal complex of the present invention (Compound 27).
  • FIG. 7 is a schematic view showing an example of a display device composed of organic EL elements.
  • FIG. 8 is a schematic diagram of display unit A.
  • FIG. 9 is a schematic diagram of a pixel.
  • FIG. 10 is a schematic diagram of a passive matrix type full-color display device.
  • FIG. 11 is a schematic view of a lighting device.
  • FIG. 12 is a schematic diagram of a lighting device.
  • the organic EL element material of the present invention it is possible to molecularly design a useful organic EL element material for an organic EL element by any one of claims 1 to 9, and the configuration specified in item 1. It worked. In addition, by using the organic EL element material, it was possible to provide an organic EL element, an illuminating device, and a display device that exhibit high luminous efficiency and have a long emission lifetime.
  • the inventors have found that the luminous efficiency and luminous lifetime are greatly improved.
  • the stability of the complex of the phenylazole derivative is greatly influenced by the influence of the substitution position and type of the substituent on the phenyl nucleus, which is the mother nucleus, which affects the emission lifetime. I found it to have a big impact.
  • the metal complex according to the present invention by introducing a specific partial structure into phenylazole, light is emitted only by a blue metal complex having a conventional phenylpyridine derivative as a ligand, particularly only by an electron withdrawing group. We found that the light emission lifetime, which was a problem with organic EL devices manufactured using organic EL device materials that had been controlled to have a short wavelength, was significantly improved.
  • 2-phenylimidazole derivatives 2-phenylimidazole derivatives are used, and by introducing specific substituents into nitrogen atoms that are not liganded to metals on the imidazole ring, excellent color purity is achieved. As a result, it was found that the lifetime of the blue light-emitting device could be further extended.
  • the metal complex according to the present invention is, for example, described by the above general formula (1).
  • the partial structure shown in the parenthesis having ml, or the partial structure represented by a tautomer thereof is the main ligand, m
  • a partial structure shown in parentheses having 2 or a partial structure represented by a tautomer thereof is called a subligand.
  • the metal complex is a main ligand or a tautomer thereof and a subligand or a combination of tautomers thereof.
  • m2 0, that is, all the ligands of the metal complex are composed only of a partial structure represented by the main ligand or its tautomer! /, constitution!
  • the type of ligand in the complex is preferably composed of 1 to 2 types, and more preferably 1 type.
  • the metal used for forming the metal complex represented by the general formula (1), (2) or (3) according to the present invention includes a transition metal element of group 8 to 11 of the periodic table (simply a transition).
  • a transition metal element of group 8 to 11 of the periodic table implies a transition.
  • iridium and platinum are preferable transition metal elements.
  • a light emitting layer and / or an electron blocking layer is preferred and contained in the light emitting layer.
  • it is possible to improve the external extraction quantum efficiency (increase the luminance) and prolong the light emission lifetime of the organic EL device of the present invention.
  • X represents R—N, ⁇ , S, Se or Te.
  • X is preferably R—N, 0, S in that the optical maximum wavelength is shorter.
  • X is RN in that the color purity of light emission is higher.
  • R represents a substituted, unsubstituted alkyl group, cycloalkyl group, aryl group, or aromatic complex.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert butyl group, a pentyl group, a hexyl group, an octyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, and the like. Is mentioned.
  • Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
  • Examples of the aryl group include a phenyl group, a mesityl group, a tolyl group, a xylyl group, a naphthyl group, an anthryl group, an azulenyl group, an acenaphthyl group, a fluorenyl group, a phenanthryl group, an indur group, a pyrenyl group, and a biphenyl group.
  • Examples include a tolyl group.
  • aromatic heterocyclic group examples include a pyridyl group, pyrimidinyl group, furyl group, pyrrolinole group, imidazolyl group, benzimidazolyl group, pyrazolyl group, pyrazyl group, and triazolyl group.
  • substituents examples include alkyl groups (for example, methyl group, ethyl group, propyl group, isopropyl group, tert butyl group, pentyl group, hexyl group, octyl group).
  • cycloalkyl group eg, cyclopentyl group, cyclohexyl group, etc.
  • alkenyl group eg, bur group, aryl group, etc.
  • alkynyl group eg, Etul group, propargyl group, etc.
  • aromatic hydrocarbon ring group also called aromatic carbocyclic group, aryl group, etc.
  • aromatic heterocyclic groups for example, pyr
  • G represents a substituent, and n represents 0, 1 or 2.
  • substituents include R substituent examples
  • Y, Y and Y represent R—N, N, or R—C, together with C and N, an imidazole ring,
  • R represents a substituted, unsubstituted alkyl group, a cycloalkyl group, an aryl group or an aromatic heterocyclic group.
  • alkyl group, cycloalkyl group, aryl group, and aromatic heterocyclic group are the same as those exemplified as R.
  • R is preferably a methyl group, a substituted or unsubstituted aryl group, or an aromatic heterocyclic group from the viewpoint of light emission lifetime, and particularly preferably a substituted, unsubstituted aryl group, or aromatic heterocyclic group.
  • aryl groups those in which at least one methyl group is substituted at the two ortho positions of the binding site with imidazole are more preferable than the point that the emission wavelength is shortened.
  • the two ortho positions of the binding site with imidazole are both substituted with methyl groups. Specifically, it is a 2,6-dimethylphenyl group, a mesityl group (2,4,6-trimethylphenyl group), a tetramethylphenyl group or a pentamethylphenyl group.
  • An example of a substituent that may be further substituted in the 2,6-dimethylphenyl group is the same force S as the substituent for R.
  • R is a hydrogen atom! / Represents a substituent.
  • substituent the same ones as exemplified as the substituent for R can be used.
  • a hydrogen atom or a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group or aromatic heterocyclic group is preferred, and a hydrogen atom or a substituted or unsubstituted aryl group is more preferred.
  • M as a central metal represents a group 8 to 11 metal in the periodic table.
  • preferred central metals include ruthenium, rhodium, palladium, silver, osmium, iridium, platinum, gold and the like. More preferred are iridium and platinum.
  • X, G, n, R, R, and M represent the same as those in the general formula (1).
  • Y is R—N in terms of high emission quantum yield.
  • Y is preferably H—C in that it is a force beam shortwave.
  • the emission lifetime is longer when both Y and Y are R–C.
  • the structures of imidazole-1, triazole-1, triazole-2 and tetrazole-1 are more preferable, and imidazolone 1 and triazole-1 are more preferable. Most preferred is the structure of imidazole-1.
  • a group of atoms forming a ligand is represented.
  • Specific examples of the bidentate ligand represented by XL-X include substituted or unsubstituted phenyl
  • Examples thereof include norepyridine, phenylpyrazonole, phenylimidazole, phenyltriazolene, phenyltetrazole, virazabol, acetylacetone, and picolinic acid.
  • m2 is preferably 0.
  • Figures 1 and 2 show the emission spectra.
  • Figures 3 and 4 show the emission spectra.
  • Figures 5 and 6 show the emission spectra.
  • the organic EL element material of the present invention for the light emitting layer or the electron blocking layer.
  • the light emitting layer it is preferably used as a light emitting dopant as described above.
  • the mixing ratio of the light-emitting dopant to the light-emitting host is preferably adjusted to a range of 0.;! To less than 30% by mass.
  • the luminescent dopant may be a mixture of two or more types of compounds.
  • the mixed partner may have a different structure, and other metal complexes or phosphorescent dopants or fluorescent dopants having other structures may also be used. Good.
  • Luminescent dopants can be broadly divided into two types: fluorescent dopants that emit fluorescence and phosphorescent dopants that emit phosphorescence.
  • fluorescent dopant include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes. And pyrylium dyes, perylene dyes, stilbene dyes, polythiophene dyes, and rare earth complex phosphors.
  • a typical example of the latter is preferably a complex compound containing a transition metal element of Group 8, 9, or 10 in the periodic table of elements, and more preferably an iridium compound. And osmium compounds, and most preferred is an iridium compound.
  • JP 2002-332291 A JP 2002-50484 A, JP 2002-33 2292 A, JP 2002-83684 A, Special Table 2002 — 540572, JP 20 02-117978, JP 2002-338588, JP 2002-170684, JP 2002-352960, WO 01/93642, JP 2002
  • JP 2002-100476 JP 2002-173674, JP 2002-359082, JP 2002-175884, JP 2002-363552, JP 2002-184582 Publication, JP 2003-7469, JP 2002-525 808, JP 2003-7471, JP 2002-525833, JP 2003
  • the host compound used in the present invention represents a compound having a phosphorescence quantum yield of phosphorescence emission of less than 0.01 at room temperature (25 ° C.) among compounds contained in the light emitting layer.
  • the luminescent host used in the present invention is not particularly limited in terms of structure, but is typically a power rubazole derivative, a triarylamine derivative, an aromatic borane derivative, a nitrogen-containing bicyclic compound, a thiophene derivative.
  • Basic bones such as furan derivatives and oligoarylene compounds
  • a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the force rubazole ring of the force rubazole derivative is substituted with a nitrogen atom.
  • a canolevazole derivative or a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carbazole ring of the carbazole derivative is substituted with a nitrogen atom is preferably used.
  • a plurality of known host compounds may be used in combination as a host compound.
  • These known host compounds have a hole transporting ability and an electron transporting ability, prevent the emission of longer wavelengths, and have a high Tg of 90 ° C or higher, more preferably 100 ° C or higher.
  • Glass transition temperature) compounds are preferred.
  • the glass transition point (Tg) is a value determined by a method based on JIS-K-7121 using DSC (Differential Scanning Colorimetry).
  • the light-emitting host used in the present invention may be a low-molecular compound or a high-molecular compound having a repeating unit, and a low-molecular compound having a polymerizable group such as a bur group or an epoxy group (evaporation polymerizable light-emitting). Even the host)
  • the light emitting layer may further contain a host compound having a fluorescence maximum wavelength as a host compound.
  • a host compound having a fluorescence maximum wavelength is a compound having a high fluorescence quantum yield in a solution state.
  • the fluorescence quantum yield is preferably 10% or more, particularly preferably 30% or more.
  • host compounds having a maximum fluorescence wavelength include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes. And pyrylium dyes, perylene dyes, stilbene dyes, polythiophene dyes, and the like.
  • the fluorescence quantum yield can be measured by the method described in the third edition of Experimental Chemistry Course 7, Spectroscopy II, page 362 (1992 edition, Maruzen).
  • Preferable specific examples of the layer structure of the organic EL device of the present invention are as follows. The present invention is not limited thereto.
  • the blocking layer for example, electron blocking layer, hole blocking layer
  • the blocking layer for example, electron blocking layer, hole blocking layer
  • the organic EL device material of the present invention for a hole blocking layer, an electron blocking layer, and the like.
  • the organic EL device material of the present invention is contained in a hole blocking layer and an electron blocking layer
  • the organic EL device material of the present invention described in any one of 1 to 7 above is used as a hole. It may be contained in a state of 100% by mass as a layer constituting component such as a blocking layer or an electron blocking layer, or may be mixed with other organic compounds.
  • the thickness of the blocking layer according to the present invention is preferably 3 to 100 nm, more preferably
  • the hole blocking layer has the function of an electron transport layer and the function of transporting electrons.
  • it is made of a material having a remarkably small ability to transport holes, and the recombination probability of electrons and holes can be improved by blocking holes while transporting electrons.
  • Examples of the hole blocking layer include, for example, Japanese Patent Application Laid-Open Nos. 11 204258 and 11 204359, and “The Organic EL Element and the Forefront of Industrialization (November 30, 1998, NTT Corporation)
  • the hole blocking layer described in page 237 of “Issuance)” is applicable as the hole blocking layer according to the present invention.
  • the structure of the electron carrying layer mentioned later can be used as a hole-blocking layer concerning this invention as needed.
  • the organic EL device of the present invention has a hole blocking layer as a constituent layer, and the hole blocking layer serves as a hole blocking material and forms the carbazole ring of the force rubazole derivative or the carbazole derivative. It is preferred to contain a derivative having a ring structure in which at least one of the carbon atoms of the hydrogen ring is replaced by a nitrogen atom!
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material having a function of transporting holes and an extremely small capacity of transporting electrons. The probability of recombination of electrons and holes can be improved by blocking the children. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.
  • the organic EL device material of the present invention for the adjacent layer adjacent to the light-emitting layer, that is, the hole blocking layer and the electron blocking layer, particularly for the electron blocking layer. It is preferable.
  • the hole transport layer includes a 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.
  • a single hole or multiple hole transport layers should be provided.
  • a hole transport material there is no particular limitation. Conventionally, it is commonly used as a hole charge injection / transport material in a photoconductive material, or used in a hole injection layer or a hole transport layer of an organic EL device. Any known medium force can be selected and used.
  • the hole transport material has either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives Sadiazole 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, stilbene derivatives, silazane derivatives Aniline-based copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • Typical examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N-tetraphenenole 4, A'-diaminophenolinore; N, N-diphenylenole N, N'-bis (3-Methylphenyl) 1 [1, 1'-Biphenyl] 1, 4, 4'-Diamine (TPD); 2, 2 Bis (4 di-l-triamylaminophenyl) propane; 1, 1-bis (4 di-p-tri-noraminophenyl) cyclohexane; N, N, N ', N' —tetra-p-trinore 4, A'-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) 4-aminophenyl) Hexane; bis (4-dimethylamino-2-methylphenenyl) phenylmethane; bis (4-di-p-triamylamin
  • No. 5,061,569 for example, 4, 4′-bis [ N- (1-naphthyl) N phenylamino] biphenyl (NPD), three triphenylamine units described in JP-A-4308688 are connected in a starburst type 4, 4 ', A' —Tris [N— (3-methylphenyl) N phenyla Roh] triphenyl ⁇ Min (MTD ATA) and the like.
  • these materials are introduced into the polymer chain, or these materials are combined with the polymer main chain.
  • the polymer material 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.
  • This hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • 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.
  • an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • a single layer or a plurality of layers are provided.
  • 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 as follows. The following materials are known.
  • the electron transport layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer, and any material selected from conventionally known compounds should be used. Touch with force S.
  • electron transport materials examples include heterocyclic tetrafluoride derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, and the like.
  • derivatives having a cyclic structure examples include heterocyclic tetrafluoride derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, and the like.
  • a quinoxaline derivative having a quinoxaline ring can also be used as an electron transport material.
  • these materials were introduced into the polymer chain, or these materials were combined with the polymer main chain.
  • the polymer material can also be used.
  • Metal complexes of 8 quinolinol derivatives such as tris (8 quinolinol) aluminum (Alq), tris (5, 7-dichloro-l-quinolinol) aluminum, tris (5, 7-dive mouth 8 quinolinol) Aluminum, tris (2methyl-8quinolinol) 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 Metal complexes replaced with Sn, Ga or Pb can also be used as electron transport materials.
  • 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 transport material.
  • the distyrylvirazine derivative exemplified as the material of the light emitting layer can also be used as an electron transport material, and inorganic semiconductors such as n-type Si and n-type SiC can be used as well as the hole injection layer and the hole transport layer. It can be used as an electron transport material.
  • This 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, an ink jet method, or an LB method. S can. Although there is no restriction
  • This electron transport layer may have a single layer structure composed of one or more of the above materials.
  • the injection layer is provided as necessary, and has an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or hole transport layer and between the cathode and the light emitting layer or electron transport layer. May be.
  • the injection layer is a layer provided between the electrode and the organic layer in order to lower the drive voltage and improve the luminance of the light emission.
  • the organic EL element and the forefront of industrialization June 30, 1998, NTT) 2) Chapter 2 “Electrode Materials” (pages 123-166) ”of the 2nd volume of“ E.S. Co., Ltd.) ”, the hole injection layer (anode buffer layer), the electron injection layer (cathode buffer layer) There is.
  • Lid Examples include a phthalocyanine buffer layer represented by cyanine, 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-917574, JP-A-10-74586, and the like.
  • Metal buffer layer typified by aluminum, etc., alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer typified by aluminum oxide One layer and so on.
  • the buffer layer is preferably a very thin film
  • the film thickness is preferably in the range of 0.;! To lOOnm.
  • This injection layer can be formed by thinning the above material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method.
  • the thickness of the injection layer is not particularly limited, but is usually about 5 to 5000 nm.
  • This injection layer may have a single layer structure composed of one or more of the above materials.
  • 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 Cul, indium tin oxide (ITO), SnO, and ZnO.
  • conductive transparent materials such as Cul, indium tin oxide (ITO), SnO, and ZnO.
  • ITO indium tin oxide
  • ZnO 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 can be formed into a thin film by vapor deposition or sputtering, and a pattern of the desired shape can be formed by photolithography, 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 when the electrode material is deposited or sputtered.
  • the transmittance greater than 10%
  • the sheet resistance as the anode is preferably several hundred ⁇ / mouth or less.
  • the film thickness depends on the material, it is usually selected from 10 to 1000 nm, preferably 10 to 200 nm.
  • the 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 is used.
  • an electron injecting metal a material having a low work function (4 eV or less) metal
  • an alloy a material having a low work function (4 eV or less) metal
  • an alloy a material having a low work function (4 eV or less) metal
  • an alloy referred to as an electron injecting metal
  • an alloy an electrically conductive compound
  • a mixture thereof a mixture thereof.
  • Specific examples of such electrode materials include sodium, sodium isotropic lithium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al O) 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 value 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 suitable.
  • the cathode can be made by forming a thin film of these electrode materials by vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / mouth or less.
  • the film thickness is usually 10 to 1000 nm, preferably 50 to 200 nm.
  • it is convenient that either the anode or the cathode of the organic EL element is transparent or translucent to improve the light emission luminance.
  • Substrate also referred to as substrate, substrate, support, etc.
  • the substrate of the organic EL device of the present invention is not particularly limited as long as it is transparent or transparent, and there are no particular restrictions on the type of glass, plastic, etc.
  • Examples of substrates that are preferably used include glass, Examples thereof include quartz and a light-transmitting resin film.
  • a particularly preferred substrate is a resin film that can give flexibility to the organic EL element.
  • Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheroletherketone, polyphenylenesulfide, polyarylate, polyimide, polycarbonate (PC ), A film made of cellulose triacetate (TAC), cellulose acetate propionate (CAP) or the like.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PES polyethersulfone
  • PES polyetherimide
  • polyetheroletherketone polyphenylenesulfide
  • PC polycarbonate
  • a film made of cellulose triacetate (TAC), cellulose acetate propionate (CAP) or the like On the surface of the resin film, an inorganic or organic film or a hybrid film of both of them may be formed, and the water vapor transmission rate is 0.01 g / m 2 'day atm or less.
  • a film is preferred.
  • the external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 2% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted outside the organic EL element / the number of electrons X I 00 flowed to the organic EL element.
  • a hue improving filter such as a color filter may be used in combination.
  • a roughened film such as anti-glare phenolic
  • a roughened film may be used in combination in order to reduce unevenness in light emission.
  • anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode force I will explain to you!
  • a desired electrode material for example, a thin film having a material force for an anode
  • a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 111 m or less, preferably 10 to 200 nm.
  • an anode is produced.
  • a thin film containing an organic compound such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, or an electron transport layer, which is an element material, is formed thereon.
  • a method of thinning a thin film containing an organic compound there are a spin coat method, a cast method, an ink jet method, a vapor deposition method, a printing method, and the like.
  • the vacuum deposition method or the spin coating method is particularly preferable because it is difficult to form. Further, different film forming methods may be applied for each layer.
  • the deposition conditions may vary due to kinds of materials used, generally boat temperature 50 to 450 ° C, vacuum degree of 10- 6 ⁇ ; 10- 2 Pa, deposition rate 0 0;! -50 nm / sec, substrate temperature 50-300 ° C., film thickness 0.1-5 m are preferably selected as appropriate.
  • a thin film made of a cathode material is formed thereon with a thickness of 1 ⁇ m or less, preferably 50
  • a desired organic EL device can be obtained by forming the film so as to have a film thickness in the range of ⁇ 200 nm by, for example, vapor deposition or sputtering, and providing a cathode.
  • the organic EL device is preferably manufactured from the hole injection layer to the cathode consistently by a single vacuum, but it may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
  • the display device of the present invention will be described.
  • the display device of the present invention has the organic EL element.
  • the display device of the present invention may be monochromatic or multicolor, but here, a multicolor display device will be described.
  • a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by a vapor deposition method, a casting method, a spin coating method, an ink jet method, a printing method, or the like.
  • the method is not limited, but the vapor deposition method, the ink jet method, and the printing method are preferable.
  • patterning with a shadow mask is preferred.
  • the production order can be reversed, and the cathode, the electron transport layer, the hole blocking layer, the light emitting layer, the hole transport layer, and the anode can be produced in this order.
  • the multicolor display device can be used as a display device, a display, and various light emitting sources.
  • full-color display is possible by using three organic EL elements, blue, red, and green light emission.
  • Examples of display devices and displays include televisions, personal computers, mopile devices, AV devices, character broadcast displays, and information displays in automobiles.
  • it may be used as a display device for playing back still images and moving images
  • the drive method when used as a display device for moving image playback is either a simple matrix (passive matrix) method or an active matrix method. It may be.
  • Light emitting sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sensors Examples include light sources, but are not limited to this!
  • the lighting device of the present invention will be described.
  • the lighting device of the present invention has the organic EL element.
  • the organic EL element having the resonator structure may be used as an organic EL element having a resonator structure in the organic EL element of the present invention.
  • Examples include a light source of an electrophotographic copying machine, a light source of an optical communication processor, a light source of an optical sensor, and the like. Moreover, you may use for the said use by making a laser oscillation.
  • the organic EL device of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, a still image or a moving image directly visible It may be used as a type of display device (display).
  • the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
  • a full-color display device can be manufactured by using two or more organic EL elements of the present invention having different emission colors.
  • FIG. 7 is a schematic view showing an example of a display device composed of organic EL elements.
  • FIG. 2 is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.
  • the display 1 includes a display section A having a plurality of pixels, a control section B that performs image scanning of the display section A based on image information, and the like.
  • the control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside. Sequentially emits light according to the image data signal, scans the image, and sends the image information to the display unit A.
  • FIG. 8 is a schematic diagram of display unit A.
  • the display portion A includes a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of pixels on a substrate.
  • the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).
  • 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 grid pattern and are connected to the pixels 3 at the orthogonal positions (details Is not shown).
  • the pixel 9 When a scanning signal is applied from the scanning line 5, the pixel 9 receives an image data signal from the data line 6, and emits light according to the received image data.
  • Full color display is possible by arranging pixels in the red region, the green region, and the blue region as appropriate on the same substrate.
  • FIG. 9 is a schematic diagram of a pixel.
  • the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
  • organic EL elements that emit red, green, and blue as the organic EL elements 10 in multiple pixels, and arranging them on the same substrate in parallel, full-color display can be achieved with power S.
  • an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
  • a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5
  • the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is transferred to the capacitor 13 and the driving transistor. It is transmitted to the gate of the star 12.
  • the capacitor 13 is charged according to the potential of the image data signal.
  • Drive transistor 12 has a drain Is connected to the power supply line 7 and the source is connected to the electrode of the organic EL element 10, and current is supplied from the power supply line 7 to the organic EL element 10 according to the potential of the image data signal applied to the gate. .
  • the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied.
  • the organic EL device 10 continues to emit light until it is seen.
  • the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
  • the organic EL element 10 emits light by providing a switching transistor 11 and a driving transistor 12 as active elements for each of the plurality of pixels.
  • Element 10 is emitting light.
  • Such a light emitting method is called an active matrix method.
  • the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials.
  • the light emission amount may be on or off.
  • the potential of the capacitor 13 can be maintained until the next scanning signal is applied, or can be discharged immediately before the next scanning signal is applied! /.
  • the present invention is not limited to the above-described active matrix method, and may be a passive matrix type light emission drive in which an organic EL element emits light according to a data signal only when a scanning signal is scanned. .
  • FIG. 10 is a schematic diagram of a display device using a passive matrix method.
  • a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
  • the pixel 3 connected to the applied scanning line 5 emits light in accordance with the image data signal.
  • the noisy matrix method has no active element in pixel 3, and can reduce manufacturing costs.
  • the organic EL material of the present invention can be applied to an organic EL element that emits substantially white light as a lighting device.
  • a plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials, and white light emission is obtained by mixing colors.
  • the combination of multiple emission colors may include three emission maximum wavelengths of the three primary colors of blue, green, and blue, or the complementary colors such as blue and yellow, and blue-green and orange are used 2 It may be one containing two emission maximum wavelengths.
  • a combination of light emitting materials for obtaining a plurality of light emission colors is a combination of a plurality of phosphorescent or fluorescent materials, a light emitting material that emits fluorescence or phosphorescence, and a combination of light emitting materials. Any combination with a dye material that emits light as excitation light may be used, but in the white organic EL device according to the present invention, only a combination of a plurality of light-emitting dopants may be mixed.
  • a mask is provided only at the time of formation of the light emitting layer, hole transport layer, electron transport layer, etc.
  • an electrode film can be formed on one side by vapor deposition, casting, spin coating, ink jet, printing, etc., and productivity is improved. According to this method, unlike the white organic EL device in which light emitting elements of a plurality of colors are arranged in parallel in an array, the elements themselves emit white light.
  • the white light-emitting organic EL device is not only the display device and the display, but also a variety of light-emitting light sources and lighting devices, such as home lighting, interior lighting, and exposure light source. It is also useful for display devices such as backlights for liquid crystal display devices.
  • backlights for watches, signboard advertisements, traffic lights, optical storage media and other light sources, light sources for electronic photocopiers, light sources for optical communication processors, light sources for optical sensors, and display devices are required. And a wide range of uses such as general household appliances.
  • the transparent support substrate with this ITO transparent electrode was ultrasonically cleaned with isopropyl alcohol Then, it was dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • This transparent support substrate is fixed to the substrate holder of a commercially available vacuum evaporation system, while ⁇ -NPD, H4, Ir 12, BCP, and Alq are placed in five tantalum resistance heating boats, respectively. Attached to the tank).
  • lithium fluoride was put in a resistance heating boat made of tantalum, and aluminum was put in a resistance heating boat made of tungsten, respectively, and attached to the second vacuum chamber of the vacuum evaporation apparatus.
  • the heating boat containing H4 and the boat containing Ir 12 are independently energized, so that the deposition rate of H4 as a light emitting host and Ir-12 as a light emitting dopant is 100: 6.
  • the light emitting layer was provided by vapor deposition so that the film thickness was 30 nm.
  • the heating boat containing BCP was energized and heated, and a hole blocking layer having a thickness of 10 nm was provided at a deposition rate of 0.2;! To 0.2 nm / sec. Further, the heating boat containing Alq was energized and heated, and an electron transport layer having a film thickness of 20 nm was provided at a deposition rate of 0.2; /-0.2 nm / sec.
  • the organic EL devices 1-2-1 to 26 were prepared in the same manner except that the light emitting host, the light emitting dopant, and the hole blocking material were changed as shown in Table 1.
  • the non-light emitting surface of each organic EL device after fabrication was covered with a glass case, and a glass substrate having a thickness of 300 m was used as a sealing substrate.
  • the epoxy photo-curing adhesive (Latus Track LC0629B manufactured by Toagosei Co., Ltd.) is applied as a sealant around the periphery, and this is overlaid on the cathode and brought into close contact with the transparent support substrate. It was irradiated with UV light, cured, sealed, and evaluated by forming an illumination device as shown in FIGS.
  • FIG. 11 shows a schematic diagram of a lighting device, in which the organic EL element 101 is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is to bring the organic EL element 101 into contact with the atmosphere.
  • a glove box under a nitrogen atmosphere under a high purity nitrogen gas atmosphere with a purity of 99.999% or more.
  • FIG. 12 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 organic EL device was continuously lit at room temperature at a constant current of 2.5 mA / cm 2 and the time required to reach half the initial luminance was measured.
  • Luminous lifetime is organic EL
  • the element 1 1 is expressed as a relative value set to 100.
  • the organic EL device was visually evaluated for the luminescent color when it was lit continuously at room temperature under a constant current condition of 2.5 mA / cm2.
  • the organic EL device produced using the metal complex according to the present invention has higher emission efficiency and longer lifetime while having a short-wave emission of pure blue to blue-green compared to the organic EL device of the comparative example. It is clear that a long life can be achieved.
  • Polyburcarbazole hole transporting binder polymer
  • Ir 1 13 blue light emitting orthometalated complex
  • 4-Oxadiazole electron transport material
  • a mass patterned on this organic compound layer (A mask with a light emitting area of 5 mm x 5 mm), and depositing 0.5 nm of lithium fluoride as the cathode buffer layer and 150 nm of aluminum as the cathode in the vapor deposition system, providing the cathode, and emitting blue organic EL Element 2-1 was produced.
  • Organic EL elements 2-2 to 2-11 were prepared in the same manner as in the preparation of organic EL element 2-1, except that the luminescent dopant was changed as shown in Table 2.
  • the non-light emitting surface of each organic EL device after fabrication was covered with a glass case, and a glass substrate having a thickness of 300 m was used as the sealing substrate.
  • the epoxy-based photo-curing adhesive (Latus Track LC0629B manufactured by Toagosei Co., Ltd.) is applied as a sealant around the glass substrate, and this is overlaid on the cathode and brought into close contact with the transparent support substrate. Then, UV light was irradiated, cured, sealed, and an illumination device as shown in FIGS. 11 and 12 was formed and evaluated.
  • the organic EL device produced using the metal complex according to the present invention has high luminous efficiency and high luminance while having a short blue light emission of pure blue to blue green compared with the organic EL device of the comparative example. It is clear that can be achieved.
  • the organic EL device 1-118 of Example 1 was used as a blue light emitting device.
  • a green light-emitting device was produced in the same manner as in Example 1 except that Ir-12 was changed to Ir-1 in the organic EL device 11 of Example 1, and this was used as a green light-emitting device.
  • a red light-emitting device was produced in the same manner as in Example 1 except that Ir-12 was changed to Ir-9 in the organic EL device 1-11, and this was used as a red light-emitting device.
  • FIG. 8 shows only a schematic diagram of the display portion A of the display device thus manufactured. That is, 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.
  • a plurality of pixels 3 light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.
  • Scanning line of wiring part 5 and the plurality of data lines 6 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 (details are not shown).
  • the plurality of pixels 3 are driven by switches that are organic EL elements and active elements corresponding to the respective emission colors.
  • the pixel 3 receives and receives an image data signal from the data line 6. Emits light according to the image data. In this way, a full-color display device was produced by appropriately juxtaposing red, green, and blue pixels.
  • the electrode of the transparent electrode substrate of Example 1 was patterned to 20 mm x 20 mm, and ⁇ -NPD was deposited to a thickness of 25 nm as a hole injection / transport layer on the same as in Example 1, and then H4
  • the heating boat containing, the boat containing Illustrative Compound (4), and the boat containing Ir 9 were energized independently, respectively, and CBP as the luminescent host and Illustrative Compound (4) and Ir as the luminescent dopant were respectively supplied.
  • the deposition rate of 9 was adjusted to 100: 5: 0.6, deposition was performed to a thickness of 30 nm, and a light emitting layer was provided.
  • a 10-nm BCP film was formed to provide a hole blocking layer. Furthermore, Alq was deposited at 40 nm to provide an electron transport layer.
  • Example 2 a square perforated mask having substantially the same shape as the transparent electrode made of stainless steel was placed on the electron injection layer, and lithium fluoride 0.5 nm was used as a cathode buffer layer and a cathode. Aluminum 150nm was deposited.
  • This element was provided with a sealing can having the same method and the same structure as in Example 1, and FIG.
  • the ITO transparent electrode is formed after patterning on a substrate ( ⁇ Techno Glass Co., Ltd. 45-45) made of ITO (Indium Toxide) on a lOOmmX lOOmm X l. 1mm 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.
  • PEDOT / PSS polystyrene sulfonate
  • 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 perform photopolymerization / crosslinking, vacuum drying was performed at 60 ° C. for 1 hour to form a second hole transport layer.
  • this substrate was fixed to the substrate holder of the vacuum evaporation apparatus, and the resistance made of molybdenum was added.
  • 200 mg of Alq was put into a heat boat and attached to a vacuum evaporation system. After pressure in the vacuum tank was reduced by 4 X 10- 4 Pa or, and heated by supplying an electric current to the boat charged with Alq, it is deposited on the electron transport layer at a deposition rate of 0. lnm / sec, further film An electron transport layer with a thickness of 40 nm was provided.
  • the substrate temperature during vapor deposition was room temperature.
  • a white light emitting organic EL device was produced.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un matériau de dispositif électroluminescent organique ayant une longueur d'onde d'émission contrôlée, un rendement lumineux élevé et une longue durée de vie d'émission. En particulier, l'invention concerne un matériau de dispositif électroluminescent organique qui émet une lumière de courte longueur d'onde se situant dans la plage du bleu au bleu-vert, tout en ayant un rendement lumineux élevé et une longue durée de vie d'émission. L'invention concerne également un dispositif électroluminescent organique, un dispositif d'affichage et un dispositif d'éclairage, chacun utilisant un tel matériau de dispositif électroluminescent organique. Le matériau de dispositif électroluminescent organique est caractérisé par le fait qu'il est composé d'un complexe métallique représenté par la formule générale suivante (1).
PCT/JP2007/068063 2006-09-20 2007-09-18 Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, dispositif d'affichage et d'éclairage WO2008035664A1 (fr)

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Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2008035571A1 (ja) * 2006-09-20 2010-01-28 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子
JP2013010752A (ja) * 2011-06-03 2013-01-17 Semiconductor Energy Lab Co Ltd 有機金属錯体、有機発光素子、発光装置、電子機器、及び照明装置
WO2013027633A1 (fr) * 2011-08-19 2013-02-28 コニカミノルタホールディングス株式会社 Elément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage
EP2565249A1 (fr) * 2011-08-31 2013-03-06 Universal Display Corporation Complexes de Pt (II) cyclométallés tétradentés
WO2013038843A1 (fr) 2011-09-12 2013-03-21 新日鉄住金化学株式会社 Élément électroluminescent organique
WO2013038929A1 (fr) 2011-09-12 2013-03-21 新日鉄住金化学株式会社 Matériau pour élément électroluminescent organique ayant une structure de cycle à quatre chaînons contenant du silicium, et élément électroluminescent organique l'utilisant
WO2013038804A1 (fr) 2011-09-12 2013-03-21 新日鉄住金化学株式会社 Élément électroluminescent organique
WO2013088934A1 (fr) 2011-12-12 2013-06-20 新日鉄住金化学株式会社 Matériau d'élément électroluminescent organique et élément électroluminescent organique qui utilise ce dernier
KR20130084615A (ko) * 2012-01-17 2013-07-25 유니버셜 디스플레이 코포레이션 신규한 헤테로렙틱 이리듐 착물
WO2013137162A1 (fr) * 2012-03-15 2013-09-19 コニカミノルタ株式会社 Élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage
WO2013137001A1 (fr) 2012-03-12 2013-09-19 新日鉄住金化学株式会社 Élément électroluminescent organique
WO2014002629A1 (fr) 2012-06-28 2014-01-03 新日鉄住金化学株式会社 Élément à électroluminescence organique et matériau pour un élément à électroluminescence organique
WO2014013936A1 (fr) 2012-07-19 2014-01-23 新日鉄住金化学株式会社 Élément électroluminescent organique
WO2014050904A1 (fr) 2012-09-28 2014-04-03 新日鉄住金化学株式会社 Composé pour éléments électroluminescents organiques, et élément électroluminescent organique
KR20140070412A (ko) 2012-11-30 2014-06-10 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
WO2014097813A1 (fr) 2012-12-17 2014-06-26 新日鉄住金化学株式会社 Élément électroluminescent à champ électrique organique
KR20140109270A (ko) 2013-03-01 2014-09-15 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 금속 착체, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
US8889858B2 (en) 2012-04-20 2014-11-18 Semiconductor Energy Laboratory Co., Ltd. Phosphorescent organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
US9127032B2 (en) 2011-12-23 2015-09-08 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
US9260463B2 (en) 2011-11-30 2016-02-16 Semiconductor Energy Laboratory Co., Ltd. Substituted pyrimidinato iridium complexes and substituted pyrazinato iridium complexes having an alicyclic diketone ligand
KR20160019926A (ko) 2013-06-14 2016-02-22 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 금속 이리듐 착체, 발광 소자, 발광 장치, 및 조명 장치
US9276222B2 (en) 2013-06-28 2016-03-01 Semiconductor Energy Laboratory Co., Ltd. Organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
US9273079B2 (en) 2011-06-29 2016-03-01 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
US9412956B2 (en) 2013-09-12 2016-08-09 Semiconductor Energy Laboratory Co., Ltd. Organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
JP2016186082A (ja) * 2010-11-26 2016-10-27 株式会社半導体エネルギー研究所 発光材料、発光素子、発光装置、電子機器、照明装置
US9741946B2 (en) 2012-12-20 2017-08-22 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element containing organic iridium exhibits blue-green to blue light emission
JP2018050056A (ja) * 2009-11-02 2018-03-29 株式会社半導体エネルギー研究所 発光素子、表示装置、電子機器、及び照明装置
US9978962B2 (en) 2014-05-30 2018-05-22 Semiconductor Energy Laboratory Co., Ltd. Organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
US10388891B2 (en) 2015-04-01 2019-08-20 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004067658A (ja) * 2002-06-10 2004-03-04 Mitsubishi Chemicals Corp 有機金属錯体、およびこれを用いた有機電界発光素子
WO2006009024A1 (fr) * 2004-07-23 2006-01-26 Konica Minolta Holdings, Inc. Dispositif et affichage électroluminescents organiques et dispositif d’éclairage
WO2007029461A1 (fr) * 2005-09-02 2007-03-15 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, son procédé de fabrication, affichage comprenant un tel dispositif électroluminescent organique, et dispositif d'éclairage
WO2007108362A1 (fr) * 2006-03-17 2007-09-27 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, dispositif d'éclairage et d'affichage
WO2007108459A1 (fr) * 2006-03-23 2007-09-27 Konica Minolta Holdings, Inc. Dispositif electroluminescent organique, dispositif d'affichage et dispositif d'eclairage
WO2007108327A1 (fr) * 2006-03-17 2007-09-27 Konica Minolta Holdings, Inc. Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage
JP2007262135A (ja) * 2006-03-27 2007-10-11 Showa Denko Kk 高分子発光材料、有機エレクトロルミネッセンス素子および表示装置

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4427947B2 (ja) * 2002-11-18 2010-03-10 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子及び表示装置
ATE522539T1 (de) * 2003-07-22 2011-09-15 Idemitsu Kosan Co Iridiumorganischer komplex und elektrolumineszenzgerät, in dem dieser verwendet wird
JP4337475B2 (ja) * 2003-08-27 2009-09-30 三菱化学株式会社 有機金属錯体、発光材料、および有機電界発光素子
JP2006074176A (ja) * 2004-08-31 2006-03-16 Mitsubishi Materials Corp 通信機器
JP4894513B2 (ja) * 2004-06-17 2012-03-14 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5151001B2 (ja) * 2004-07-15 2013-02-27 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP5040077B2 (ja) * 2004-07-23 2012-10-03 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子
JP2006074177A (ja) * 2004-08-31 2006-03-16 Toshiba Corp 電子機器
JP4285754B2 (ja) * 2004-09-09 2009-06-24 近畿車輌株式会社 鉄道車両用灯具
JP4961664B2 (ja) * 2004-10-22 2012-06-27 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置
CN101087863B (zh) * 2004-12-23 2012-06-20 西巴特殊化学品控股有限公司 具有亲核卡宾配体的电致发光金属络合物
JP2006254127A (ja) * 2005-03-10 2006-09-21 Ricoh Co Ltd 画像記録装置および画像表示方法
JP3845106B2 (ja) * 2005-03-14 2006-11-15 株式会社エヌ・ティ・ティ・ドコモ 携帯端末、及び、認証方法
WO2008035595A1 (fr) * 2006-09-19 2008-03-27 Konica Minolta Holdings, Inc. Dispositifs électroluminescents organiques
JP5556014B2 (ja) * 2006-09-20 2014-07-23 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004067658A (ja) * 2002-06-10 2004-03-04 Mitsubishi Chemicals Corp 有機金属錯体、およびこれを用いた有機電界発光素子
WO2006009024A1 (fr) * 2004-07-23 2006-01-26 Konica Minolta Holdings, Inc. Dispositif et affichage électroluminescents organiques et dispositif d’éclairage
WO2007029461A1 (fr) * 2005-09-02 2007-03-15 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, son procédé de fabrication, affichage comprenant un tel dispositif électroluminescent organique, et dispositif d'éclairage
WO2007108362A1 (fr) * 2006-03-17 2007-09-27 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, dispositif d'éclairage et d'affichage
WO2007108327A1 (fr) * 2006-03-17 2007-09-27 Konica Minolta Holdings, Inc. Élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage
WO2007108459A1 (fr) * 2006-03-23 2007-09-27 Konica Minolta Holdings, Inc. Dispositif electroluminescent organique, dispositif d'affichage et dispositif d'eclairage
JP2007262135A (ja) * 2006-03-27 2007-10-11 Showa Denko Kk 高分子発光材料、有機エレクトロルミネッセンス素子および表示装置

Cited By (61)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5556014B2 (ja) * 2006-09-20 2014-07-23 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子
JPWO2008035571A1 (ja) * 2006-09-20 2010-01-28 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子
US10424745B2 (en) 2009-11-02 2019-09-24 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, display device, electronic device, and lighting device
JP2018050056A (ja) * 2009-11-02 2018-03-29 株式会社半導体エネルギー研究所 発光素子、表示装置、電子機器、及び照明装置
JP2016186082A (ja) * 2010-11-26 2016-10-27 株式会社半導体エネルギー研究所 発光材料、発光素子、発光装置、電子機器、照明装置
US9406894B2 (en) 2011-06-03 2016-08-02 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, organic light-emitting element, light-emitting device, electronic device, and lighting device
JP2013010752A (ja) * 2011-06-03 2013-01-17 Semiconductor Energy Lab Co Ltd 有機金属錯体、有機発光素子、発光装置、電子機器、及び照明装置
US9273079B2 (en) 2011-06-29 2016-03-01 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device
JPWO2013027633A1 (ja) * 2011-08-19 2015-03-19 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
WO2013027633A1 (fr) * 2011-08-19 2013-02-28 コニカミノルタホールディングス株式会社 Elément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage
US9493698B2 (en) 2011-08-31 2016-11-15 Universal Display Corporation Organic electroluminescent materials and devices
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EP2565249A1 (fr) * 2011-08-31 2013-03-06 Universal Display Corporation Complexes de Pt (II) cyclométallés tétradentés
WO2013038804A1 (fr) 2011-09-12 2013-03-21 新日鉄住金化学株式会社 Élément électroluminescent organique
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US9260463B2 (en) 2011-11-30 2016-02-16 Semiconductor Energy Laboratory Co., Ltd. Substituted pyrimidinato iridium complexes and substituted pyrazinato iridium complexes having an alicyclic diketone ligand
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JP2019178345A (ja) * 2012-01-17 2019-10-17 ユニバーサル ディスプレイ コーポレイション 新規なヘテロレプティックイリジウム錯体
KR20190057044A (ko) * 2012-01-17 2019-05-27 유니버셜 디스플레이 코포레이션 신규한 헤테로렙틱 이리듐 착물
WO2013137001A1 (fr) 2012-03-12 2013-09-19 新日鉄住金化学株式会社 Élément électroluminescent organique
JPWO2013137162A1 (ja) * 2012-03-15 2015-08-03 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
WO2013137162A1 (fr) * 2012-03-15 2013-09-19 コニカミノルタ株式会社 Élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage
US9059414B2 (en) 2012-04-20 2015-06-16 Semiconductor Energy Laboratory Co., Ltd. Phosphorescent organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
US8889858B2 (en) 2012-04-20 2014-11-18 Semiconductor Energy Laboratory Co., Ltd. Phosphorescent organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
WO2014002629A1 (fr) 2012-06-28 2014-01-03 新日鉄住金化学株式会社 Élément à électroluminescence organique et matériau pour un élément à électroluminescence organique
WO2014013936A1 (fr) 2012-07-19 2014-01-23 新日鉄住金化学株式会社 Élément électroluminescent organique
WO2014050904A1 (fr) 2012-09-28 2014-04-03 新日鉄住金化学株式会社 Composé pour éléments électroluminescents organiques, et élément électroluminescent organique
US9929356B2 (en) 2012-11-30 2018-03-27 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic appliance, and lighting device
KR20140070412A (ko) 2012-11-30 2014-06-10 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
WO2014097813A1 (fr) 2012-12-17 2014-06-26 新日鉄住金化学株式会社 Élément électroluminescent à champ électrique organique
US9741946B2 (en) 2012-12-20 2017-08-22 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element containing organic iridium exhibits blue-green to blue light emission
KR20210008109A (ko) 2013-03-01 2021-01-20 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 금속 착체, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
KR20140109270A (ko) 2013-03-01 2014-09-15 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 금속 착체, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
US10431752B2 (en) 2013-06-14 2019-10-01 Semiconductor Energy Laboratory Co., Ltd. Organometallic iridium complex, light-emitting element, light-emitting device, and lighting device
KR20160019926A (ko) 2013-06-14 2016-02-22 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 금속 이리듐 착체, 발광 소자, 발광 장치, 및 조명 장치
US9978960B2 (en) 2013-06-14 2018-05-22 Semiconductor Energy Laboratory Co., Ltd. Organometallic iridium complex, light-emitting element, light-emitting device, and lighting device
US9276222B2 (en) 2013-06-28 2016-03-01 Semiconductor Energy Laboratory Co., Ltd. Organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
US9412956B2 (en) 2013-09-12 2016-08-09 Semiconductor Energy Laboratory Co., Ltd. Organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
US9978962B2 (en) 2014-05-30 2018-05-22 Semiconductor Energy Laboratory Co., Ltd. Organometallic iridium complex, light-emitting element, light-emitting device, electronic device, and lighting device
US10388891B2 (en) 2015-04-01 2019-08-20 Semiconductor Energy Laboratory Co., Ltd. Organometallic complex, light-emitting element, light-emitting device, electronic device, and lighting device

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