WO2007058255A1 - Compose complexe de metal de transition - Google Patents

Compose complexe de metal de transition Download PDF

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Publication number
WO2007058255A1
WO2007058255A1 PCT/JP2006/322852 JP2006322852W WO2007058255A1 WO 2007058255 A1 WO2007058255 A1 WO 2007058255A1 JP 2006322852 W JP2006322852 W JP 2006322852W WO 2007058255 A1 WO2007058255 A1 WO 2007058255A1
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group
substituent
carbon atoms
nuclear
atom
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PCT/JP2006/322852
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Japanese (ja)
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Kazushi Mashima
Masami Watanabe
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Idemitsu Kosan Co., Ltd.
Osaka University
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Priority claimed from US11/516,759 external-priority patent/US20080233410A1/en
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Priority to JP2007545290A priority Critical patent/JPWO2007058255A1/ja
Publication of WO2007058255A1 publication Critical patent/WO2007058255A1/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
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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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
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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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
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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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
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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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/186—Metal complexes of the light metals other than alkali metals and alkaline earth metals, i.e. Be, Al or Mg
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to a transition metal complex compound, and more particularly to a transition metal complex compound having an electoluminescence property that can provide an organic electroluminescence element having high luminous efficiency and a method for producing the transition metal compound. It is.
  • Organic electoluminescence (EL) devices use the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. Self-luminous element. Report of low-voltage driven organic EL devices using stacked devices by Eastman Kodak's CW Tang et al. (CW Tang, SA Vanslyke, Applied Physics Letters, 51 ⁇ , 913, 1987, etc.) ) Since then, research on organic EL devices using organic materials as constituent materials has been actively conducted. Tang et al. Used tris (8-hydroxyquinolinol aluminum) for the light-emitting layer and triphenyldiamine derivative for the hole-transporting layer.
  • the advantages of the stacked structure are that it increases the efficiency of hole injection into the light-emitting layer, blocks the electrons injected from the cathode, and increases the generation efficiency of excitons generated by recombination. For example, confining excitons.
  • the device structure of the organic EL device includes a hole transport (injection) layer, a two-layer type of an electron transport light-emitting layer, or a hole transport (injection) layer, a light-emitting layer, and an electron transport (injection).
  • the three-layer type is well known.
  • the structure of the element and the formation method have been devised.
  • the light-emitting material of the organic EL element is a tris (8-quinolinolato) aluminum complex.
  • Luminescent materials such as chelate complexes, coumarin derivatives, tetraphenylbutadiene derivatives, distyrylarylene derivatives, oxadiazole derivatives, etc. are known, and it has been reported that they can emit light in the visible region from blue to red. Therefore, it is expected to realize a color display element (for example, see Patent Document 1).
  • Patent Document 1 In recent years, it has also been proposed to use a phosphorescent material in addition to a fluorescent material for the light emitting layer of an organic EL element (see, for example, Non-Patent Document 1 and Non-Patent Document 2).
  • the triplet excited state or triplet exciton is not sequentially quenched so that the anode, the hole transport layer, the organic light emitting layer, the electron transport layer (hole blocking layer),
  • a structure in which layers are stacked such as an electron transport layer and a cathode has been used, and a host compound and a phosphorescent compound have been used for an organic light emitting layer (see, for example, Patent Document 2 and Patent Document 3).
  • These patent documents are technologies related to phosphorescent materials that emit red to green light.
  • techniques relating to a light emitting material having a blue emission color have been disclosed (see, for example, Patent Document 4, Patent Document 5, and Patent Document 6).
  • Patent Documents 5 and 6 describe a ligand skeleton in which an Ir metal and a phosphorus atom are bonded, and these emit light blue but have weak bonds. The heat resistance is extremely poor.
  • Patent Document 7 similarly describes a complex in which an oxygen atom and a nitrogen atom are bonded to the central metal, but there is no description about the specific effect of the group bonded to the oxygen atom, and it is unclear.
  • Patent Document 8 discloses a complex in which nitrogen atomic energy contained in different ring structures is bonded to a central metal, and a device using the same emits blue light, but the external quantum efficiency is as low as about 5%. It has become.
  • a carbene is a two-coordinate carbon that has two electrons in the sp 2 hybrid orbit and the 2p orbit, and the combined force of the orbit into which the two electrons enter and the spin direction can have four types of structures.
  • carbene complexes are short-lived 'unstable, and are intermediates or organic intermediates in organic synthesis reactions. Power that has been used as a synthetic conversion reagent such as addition to refin Around 1991, stable carbene complexes consisting of aromatic heterocyclic structures and stable carbene complexes consisting of non-aromatic cyclic structures were discovered.
  • the acyclic carbene complex was stably obtained by stabilizing with nitrogen and phosphorus.
  • the catalytic performance is improved by combining it with a transition metal as a ligand, in recent years, expectations for a stable carbene complex have increased in the catalytic reaction in organic synthesis.
  • complexes having a carbene iridium bond include the following non-patent document 12 (tris (carbene) iridium complex that also has a non-heterocyclic carbene ligand force) and non-patent document 13 (monodentate coordination type mono-). Carbene iridium complex), but the application to the organic EL device field is described.
  • Patent Document 9 discloses the synthesis of an iridium complex having a carbene bond and its emission wavelength and device performance.
  • the energy efficiency and external quantum efficiency are low, and the emission wavelength is distributed in the ultraviolet region.
  • the sensitivity is poor. Therefore, it is not suitable for light-emitting devices in the visual wavelength range such as organic EL.
  • impurities could be mixed during device fabrication because vacuum deposition could not be performed because the decomposition temperature was low or the molecular weight was high, and the complex was decomposed during the deposition.
  • Patent Document 1 JP-A-8-239655
  • Patent Document 2 U.S. Patent No. 6,097,147
  • Patent Document 3 International Publication WO01Z41512
  • Patent Document 4 US2001Z0025108 Publication
  • Patent Document 5 US 2002/0182441 Publication
  • Patent Document 6 Japanese Patent Laid-Open No. 2002-170684
  • Patent Document 7 Japanese Unexamined Patent Publication No. 2003-123982
  • Patent Document 8 Japanese Patent Laid-Open No. 2003-133074
  • Patent Document 9 International Publication WO05Z019373
  • Non-Patent Document 2 M. A. Baldo et al Very high-efficiency green organic li ght -emitting devices based on electrophosphorescence "Applied Phys ics Letters Vol. 75 No. 1, pp4-6, July 5, 1999
  • Non-Patent Document 3 Chem. Rev. 2000, 100, p39
  • Non-Patent Document 4 Am. Chem. Soc., 1991, 113, p361
  • Non-Patent Document 5 Angew. Chem. Int. Ed., 2002, 41, pi 290
  • Non-Patent Document 6 Am. Chem. Soc., 1999, 121, p2674
  • Non-Patent Document 7 Organometallics, 1999, 18, p2370
  • Non-Patent Document 8 Angew. Chem. Int. Ed., 2002, 41, pl363
  • Non-Patent Document 9 Angew. Chem. Int. Ed., 2002, 41, pi 745
  • Non-Patent Document 10 Organometallics, 2000, 19, p3459
  • Non-Patent Document 12 Organomet. Chem., 1982, 239, C26-C30
  • Non-Patent Document 13 Chem. Commun., 2002, ⁇ 2518
  • the present invention has been made to solve the above-described problems, and an object of the present invention is to provide a novel transition metal complex compound and a method for producing a transition metal compound that realize an organic EL device having high luminous efficiency. To do.
  • the present invention provides a transition metal complex compound having a metal carbene bond represented by the following general formulas (1), (3) and (4).
  • C (carbon atom) ⁇ M represents a metal carbene bond
  • the bond indicated by a solid line (1) indicates a covalent bond
  • the bond indicated by an arrow ( ⁇ ) indicates a coordinate bond.
  • M represents a metal atom of iridium (Ir), platinum (Pt), rhodium (Rh) or palladium (Pd).
  • L 1 and L 2 each independently represent a monodentate ligand or a bridged bidentate ligand (L 1 -L 2 ) in which L 1 and L 2 are bridged.
  • k is an integer from 1 to 3
  • i is an integer from 0 to 2
  • k + i represents the valence of metal M.
  • j represents an integer of 0 to 4. When there are a plurality of i and j, L 1 and L 2 may be the same or different, and adjacent ones may be bridged together.
  • L 1 is a monovalent aromatic hydrocarbon group having 6 to 30 nuclear carbon atoms which may have a substituent, or a monovalent heterocyclic group having 3 to 30 nucleus atoms which may have a substituent.
  • L 2 is a heterocyclic ring having 3 to 30 nuclear atoms that may have a substituent, a carboxylic acid ester having 1 to 30 carbon atoms that may have a substituent, a carboxylic acid amide having 1 to 30 carbon atoms, May have a substituent, phosphine which may have a substituent, iso-tolyl which may have a substituent, It may have a substituent, may have an ether having 1 to 30 carbon atoms, or may have a substituent! ⁇ may have a thioether having 1 to 30 carbon atoms, or may have a substituent.
  • the double bond-containing compound is a monovalent group of the above-mentioned ligands when L 1 and L 2 are cross-linked.
  • Z 1 is an atom that forms a covalent bond with the metal M and is a carbon, silicon, nitrogen, or phosphorus atom
  • Z 2 is an atom that forms a covalent bond with the substituent R 1 , such as carbon
  • the B ring may have an aromatic hydrocarbon group having 3 to 40 nuclear carbon atoms or a substituent which may have a substituent. It is a good heterocyclic group having 3 to 40 nuclear atoms, Z 3 represents a nitrogen atom or CR 2, and when CR 2 is plural, plural R 2 may be the same or different.
  • R 18 each independently represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, a substituted group.
  • It may have a aralkyl group having 7 to 40 carbon atoms, a substituent, a alkenyl group having 2 to 30 carbon atoms, or a substituent, a heterocyclic group having 3 to 30 nuclear atoms, An optionally substituted alkoxy group having 1 to 30 carbon atoms, which may have a substituent, an aryloxy group having 6 to 30 nuclear carbon atoms, or a substituent, which has 3 to 30 carbon atoms of An alkylamino group, an arylamino group having 6 to 30 carbon atoms which may have a substituent, a substituent, an alkylsilyl group having 3 to 30 carbon atoms, and a substituent; It is a carboxyl-containing group having 1 to 30 carbon atoms which may have an arylylsilyl group having 6 to 30 carbon atoms or a substituent. )
  • Rings A and B may be the same or different and may be bridged by adjacent ones.
  • C (carbon atom) ⁇ M represents a metal carbene bond, and the bond indicated by an arrow ( ⁇ ) represents a coordinate bond.
  • M is the same as above, and L 2 represents a monodentate ligand.
  • j is the same as above, and when j is plural, each L 2 may be the same or different, or may be cross-linked.
  • L 2 is the same ligand as described above, and L 3 is a super strong acid, a carboxylic acid, an aldehyde, a ketone, an alcohol, a thioalcohol, a phenol, an amine having a pKa value of 10 or less.
  • Z 1 is a carbon, silicon, nitrogen or phosphorus atom; Z 3 and R 1 are the same as described above.
  • Rings A and B may be the same or different and may be bridged by adjacent ones.
  • C (carbon atom) ⁇ M represents a metal carbene bond
  • the bond indicated by a solid line (1) is a covalent bond
  • the bond indicated by an arrow ( ⁇ ) is a coordinate bond.
  • Means. M is the same as described above
  • L 2 represents a monodentate ligand.
  • j is the same as above, and when j is plural, each L 2 may be the same or different and may be cross-linked.
  • L 2 is the same ligand as defined above, L 3 , ⁇ 3 and R 1 are the same as above.
  • Rings A and B may be the same or different and may be bridged by adjacent ones.
  • the present invention also includes reacting an iridium compound represented by the following general formula (5) and an imidazolium salt represented by the following general formula (6) in the presence of a solvent and a base.
  • the present invention provides a method for producing a transition metal compound having a metal carbene bond for producing a transition metal compound represented by
  • C (carbon atom) ⁇ Ir (iridium) represents a metal carbene bond
  • the bond indicated by a solid line (one) represents a covalent bond
  • an arrow ( ⁇ The bond indicated by) means a coordination bond.
  • L 2 represents a monodentate ligand. j is the same as described above, and when j is plural, each L 2 may be the same or different and may be cross-linked.
  • L 2 is the same ligand as defined above, L 3 , ⁇ 3 and R 1 are the same as above.
  • Rings A and B may be the same or different and may be bridged by adjacent ones.
  • the present invention provides an organic EL device in which an organic thin film layer composed of one or more layers having at least a light emitting layer is sandwiched between an anode and a cathode, wherein at least one layer of the organic thin film layer is the metal
  • An organic EL element containing a transition metal complex compound having a carbene bond is provided.
  • the transition metal complex compound having a metal carbene bond of the present invention can provide an organic EL device having electoluminescence properties and high luminous efficiency. Moreover, according to the method for producing a transition metal complex compound of the present invention, the transition metal complex compound can be produced efficiently.
  • FIG. 1 is a diagram showing a 1 H-NMR ⁇ vector of intermediate c obtained in Example 1.
  • FIG. 2 is a diagram showing a 1 H-NMR ⁇ vector of intermediate d obtained in Example 1.
  • FIG. 3 is a diagram showing a 1 H-NMR spectrum of transition metal complex compound 1 obtained in Example 1.
  • FIG. 4 is a diagram showing a 1 H-NMR spectrum of transition metal complex compound 1 obtained in Example 2.
  • FIG. 5 is a diagram showing cyclic voltammetry of the transition metal complex compound 1 obtained in Example 3.
  • FIG. 6 is an X-ray crystal structure analysis of transition metal complex compound 1 obtained in Example 3.
  • FIG. 7 shows a 1 H-NMR spectrum of transition metal complex compound 2 obtained in Example 4.
  • FIG. 8 is a view showing cyclic voltammetry of the transition metal complex compound 1 obtained in Example 4.
  • FIG. 9 is a diagram showing an X-ray crystal structure analysis of transition metal complex compound 2 obtained in Example 4.
  • FIG. 10 is a diagram showing a 1 H-NMR spectrum of transition metal complex compound 3 obtained in Example 5.
  • FIG. 11 is a diagram showing a 1 H-NMR spectrum of transition metal complex compound 4 obtained in Example 6.
  • FIG. 12 is a view showing cyclic voltammetry of the transition metal complex compound 4 obtained in Example 6.
  • FIG. 13 is a diagram showing an emission spectrum at room temperature of the transition metal complex compound 4 obtained in Example 6.
  • FIG. 14 is a graph showing an emission spectrum at 77K of the transition metal complex compound 4 obtained in Example 6.
  • the transition metal complex compound of the present invention is a transition metal complex compound having a metal carbene bond represented by the following general formulas (1), (3) and (4).
  • C (carbon atom) ⁇ M represents a metal carbene bond
  • a bond indicated by a solid line (-) represents a covalent bond
  • a bond indicated by an arrow ( ⁇ ) represents a coordinate bond.
  • M represents a metal atom of iridium (Ir), platinum (Pt), rhodium (Rh) or palladium (Pd), and Ir is preferred! /.
  • L 1 and L 2 each independently represent a monodentate ligand or a bridged bidentate ligand (L 1 L 2 ) in which L 1 and L 2 are bridged.
  • k is an integer from 1 to 3
  • i is an integer from 0 to 2
  • k + i represents the valence of metal M.
  • j represents an integer of 0 to 4.
  • L 1 and L 2 may be the same or different from each other, and may be cross-linked with each other.
  • L 1 is a monovalent aromatic hydrocarbon group having 6-30 nuclear carbon atoms which may have a substituent, and 3-30 nuclear atoms optionally having a substituent.
  • a monovalent heterocyclic group a monovalent carboxyl-containing group having 1 to 30 carbon atoms which may have a substituent, a monovalent amino group or a hydroxyl group-containing hydrocarbon group which may have a substituent, a substituent;
  • These alkenyl groups, substituents, aralkyl groups having 7 to 40 carbon atoms, and when L 1 and L 2 are crosslinked, are divalent groups of the above groups.
  • the aromatic hydrocarbon group is preferably one having a nuclear carbon number of 6 to 18, for example, a phenol group, 1 naphthyl group, 2 naphthyl group, 1 anthryl group, 2 anthryl group, 9-a Enthryl group, 1 phenanthryl group, 2 phenanthryl group, 3 phenanthryl group, 4 phenanthryl group, 9 phenanthryl group, 1 naphthacene group, 2 naphthacetyl group, 9-naphthaphthal group, 1-pyrole group , 2 pyreyl group, 4 pyreyl group, 2 biphenyl group, 3—biphenyl group, 4-biphenyl group, p terferyl group 4 —yl group, p terferlu group 3— P-group, p-Terfer-Lu 2-yl group, m-Ter-Fel-Lu 4-Yel group, m-Ter-Fel-Lu 3-
  • a phenyl group 1 naphthyl group, 2 naphthyl group, 9 phenanthryl group, 2 biphenylyl group, 3 biphenylyl group, 4 biphenylyl group, p-tolyl group, 3, 4 Xylylenyl group and the like and divalent groups thereof.
  • heterocyclic group examples include those having 3 to 18 nuclear atoms.
  • 2-pyridyl group 1-indolidyl group, 2-indolidyl group, 3-indolidyl group, 5-indolidyl group, 6-indolidyl group, 7 —Indolizyl group, 8 Indolizyl group, 2 Imidazopyridyl group, 3 Imidazopyridinyl group, 5 Imidazopyridinyl group, 6—Imidazopyridyl group, 7—Imidazopyridyl group, 8—Imidazopyridyl group Group, 3-pyridyl group, 4 pyridyl group, 1 indolyl group, 2 indolyl group, 3—indolyl group, 4 indolyl group, 5—indolyl group, 6—indolyl group, 7—in Drill group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindodolyl
  • Examples of the cycloalkyl and cycloalkylene groups include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1 norbornyl group, and 2- And norborol groups and the like and divalent groups thereof.
  • alkyl group and alkylene group those having 110 carbon atoms are preferable, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group.
  • methyl, ethyl, propyl, isopropyl, n-butyl, sbutyl, isobutyl, tbutyl, n-pentyl, n-hexyl, and n- are preferred.
  • the alkaryl group and the alkellene group are preferably those having 2 to 16 carbon atoms.
  • bur group, aralkyl group, 1-butenyl group, 2 butenyl group, 3 butenyl group, 1, 3 Butane gel group 1-methyl beryl group, styryl group, 2,2 diphenyl beryl group, 1,2-diphenyl beryl group, 1-methyl beryl group, 1,1-dimethyl allyl group, 2-methyl beryl group 1-Furaryl group, 2-Feraryl group, 3-Feraryl group, 3, 3-Difuryl-Rulyl group, 1,2 Dimethylaryl group, 1-Fu-Lu 1-Butul group, 3-Fuenyl 1-Butenyl And a group having these as a divalent group, preferably a styryl group, a 2,2-diphenyl-vinyl group, a 1,2-diphenyl-vinyl group, and a divalent group thereof. It is what.
  • Preferred examples of the aralkyl group and the aralkylene group include those having 7 to 18 carbon atoms, such as benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2 —Phenylisopropyl group, phenyl t-butyl group, ⁇ -naphthylmethyl group, 1 ⁇ -naphthylethyl group, 2-a naphthylethyl group, 1-a naphthylisopropyl group, 2-a naphthylisopropyl group, 13 naphthylmethyl group, 1 ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolylmethyl group,
  • L 2 is a heterocyclic ring having 3 to 30 nuclear atoms which may have a substituent, a carboxylic acid ester having 1 to 30 carbon atoms which may have a substituent, A carboxylic acid amide having 1 to 30 carbon atoms, an amine that may have a substituent, a phosphine that may have a substituent, an iso-tolyl that may have a substituent, and a substituent. From ethers having 1 to 30 carbon atoms, substituents, thioethers having 1 to 30 carbon atoms, or substituents having double bond containing compounds having 1 to 30 carbon atoms When L 1 and L 2 are bridged, they are monovalent groups of the respective ligands.
  • heterocyclic ring examples include those in which the group in the example similar to that described above for L 1 is zero-valent.
  • carboxylic acid esters examples include methyl formate, ethyl formate, methyl acetate, ethyl acetate, methyl propionate, ethyl propionate, methyl benzoate, ethyl benzoate, methyl 2-pyridinecarboxylate, ethyl pyridinecarboxylate, 3 Methyl pyridine carboxylate, ethyl 3-pyridinecarboxylate, 4 methyl pyridinecarboxylate, 4 ethyl pyridinecarboxylate, methyl chloroacetate, ethyl chloroacetate, methyl 2-pyridine acetate, ethyl pyridine pyridine, 3 Methyl pyridine acetate, 3 Pyridine acetate
  • Examples include chill, methyl 4-pyridineacetate, ethyl 4-pyridineacetate, methyl 2-pyrrolecarboxylate, methyl 3-pyrrolecarboxylate, methyl 2-thiophenecarboxylate
  • Examples of the carboxylic acid amide include N, N dimethylformamide, N, N dimethylacetamide, N, N dimethylbenzoic acid amide, N, N dimethyl-2-pyridine, rubonic acid amide, N, N dimethyl-3- Pyridinecarboxylic acid amide, N, N dimethyl-4-pyridinecarboxylic acid amide, N, N dimethylphenol acetate, N, N dimethyl-2-pyridine acetate, N, N dimethyl-3 pyridine acetate, N, N dimethyl Cyl-4 pyridineacetamide, N, N dimethyl-2-pyrrolecarboxylic acid amide, N, N dimethyl-3 pyrrolecarboxylic acid amide, N, N dimethyl-2-thiophenecarbonic acid amide, N, N dimethyl-3-thiophenecarboxylic acid amide , N-methylformamide, N-methylacetamide, N-methylbenzoic acid amide, N-methyl-2-pyridine Rubonic acid amide, N-methylform
  • Examples of the amine include triethylenamine, tri-n-propylamine, tri-n-butylamine, N, N dimethylaniline, methyldiphenylamine, triphenylamine, dimethyl (2 Pyridine) amine, dimethyl (3 pyridine) amine, dimethyl (4 pyridine) amine, methylbis (2 pyridine) amine, methylbis (3-pyridine) amine, methylbis (4-pyridine) amine, tris (2 pyridine) amine, tris (3 pyridine) amine, tris (4 pyridine) amine, diisopropylamine, di-n-propylamine, di-n-butylamine, N -Methylamine, methylphenolamine, diphenylamine, methyl (2-pyridine) amine, methyl (3 pyridine) amine, methyl (4 pyridine) amine, methyl (2 pyridine) amine, methyl (3 pyridine) amine, Methyl (4 pyridine),
  • Examples of the phosphine include those obtained by replacing nitrogen of the amine with phosphorus.
  • iso-tolyl examples include butyl isocyanide, isobutyl isocyanide, sec-butyl isocyanide, t-butyl isocyanide, phenol isocyanide, 2-tolyl isocyanide, 3 tolyl isocyanide, 4 tolyl isocyanide, 2 pyridine isocyanide, 3 pyridine isocyanide. 4-pyridine isocyanide, benzyl isocyanide and the like.
  • ether examples include jetyl ether, di- n -propyl ether, di-n-butinoleethenole, diisobutinoleethenole, di-sec butinoleethenole, di-t-butyl ether, anisole, diphenyl ether, furan, Tetrahydrofuran, dioxane and the like can be mentioned.
  • Examples of the thioether include those obtained by replacing oxygen in the ether with sulfur.
  • Examples of the compound having a double bond having 1 to 30 carbon atoms include ethylene, propylene, 1-butene, 1 pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene and 1 eicosene.
  • Z 1 is an atom that forms a covalent bond with the metal M, and includes carbon, silicon, A nitrogen or phosphorus atom
  • Z 2 is an atom that forms a covalent bond with the substituent R 1 and is a carbon, silicon, nitrogen or phosphorus atom
  • the A ring and the B ring containing Z 1 and Z 2 are V, an aromatic hydrocarbon group having 3 to 40 carbon atoms, or a heterocyclic group having 3 to 40 nuclear atoms.
  • Examples of this aromatic hydrocarbon group are the same as those mentioned above, and examples of this aromatic heterocyclic group include those which are aromatic heterocyclic groups among the examples of the heterocyclic group. It is
  • Is preferably a structure represented by the following.
  • M is other than the force Ir exemplified as Ir.
  • X represents a ring structure including an adjacent B ring.
  • the bond between X and Ir ( ⁇ ) is omitted.
  • Is preferably a structure represented by the following.
  • M is other than the force Ir exemplified as Ir.
  • the A ring structure containing R 1 and Z 1 and Z 2 is simply abbreviated as A ring. Also, the A ring and Ir bond (one) is omitted.
  • Z 3 represents a nitrogen atom or CR 2, and when CR 2 is plural, plural R 2 may be the same or different! /! /.
  • each R 18 is independently a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, Aromatic hydrocarbon group with 6 to 30 carbon atoms, may have a substituent!
  • Heterocyclic group having 3 to 30 nucleus atoms, alkoxy group having 1 to 30 carbon atoms which may have a substituent, and substituents having 6 to 30 nucleus carbon atoms May have an aryloxy group, a substituent, an alkylamino group having 3 to 30 carbon atoms, an arylamino group having 6 to 30 carbon atoms which may have a substituent, or a substituent, may have a carbon number It may be an alkylsilyl group having 3 to 30 carbon atoms, a substituent, an arylsilylsilyl group having 6 to 30 carbon atoms, or a substituent, or a carboxyl-containing group having 1 to 30 carbon atoms. )
  • the alkyl group is preferably one having 1 to LO carbon atoms, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n Pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n tridecyl group, n- tetradecyl group, n Pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1 pentylhexyl
  • methyl, ethyl, propyl, isopropyl, n-butyl, sbutyl, isobutyl, tbutyl, n-pentyl, and n-hexyl are preferred.
  • the halogenated alkyl group is preferably one having 1 to 10 carbon atoms.
  • a fluoromethyl group preferred are a trifluoromethyl group, a pentafluoroethyl group, a perfluoroisopropyl group, a perfluorobutyl group, and a perfluorocyclohexyl group.
  • the aromatic hydrocarbon group is preferably one having a nuclear carbon number of 6 to 18, for example, a phenol group, 1 naphthyl group, 2 naphthyl group, 1 anthryl group, 2 anthryl group, 9-a Enthryl group, 1 phenanthryl group, 2 phenanthryl group, 3 phenanthryl group, 4 phenanthryl group, 9 phenanthryl group, 1 naphthacene group, 2 naphthacetyl group, 9-naphthaphthal group, 1-pyrole group , 2 pyreyl group, 4 pyreyl group, 2 biphenyl group, 3—biphenyl group, 4-biphenyl group, p terferyl group 4 —yl group, p terferlu group 3— P-group, p-terferreux 2—sil-group, m-terferreux 4 Group, m-terferyl 3-myl group, m-terfer
  • a phenyl group 1 naphthyl group, 2 naphthyl group, 9 phenanthryl group, 2 biphenylyl group, 3 biphenylyl group, 4 biphenylyl group, p-tolyl group, 3, 4-Xylylenyl group.
  • cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group. Groups and the like.
  • aralkyl group those having 7 to 18 carbon atoms are preferred, for example, a benzyl group,
  • the alkenyl group is preferably one having 2 to 16 carbon atoms.
  • a bur group a allyl group, a 1-butur group, a 2 butur group, a 3 butur group, a 1, 3 butane angel group.
  • the heterocyclic group preferably has 3 to 18 nuclear atoms.
  • 2-pyridyl group 1-indolidyl group, 2-indolidyl group, 3-indolidyl group, 5-indolidyl group, 6-indolidyl group, 7 —Indolizyl group, 8 Indolizyl group, 2 Imidazopyridyl group, 3 Imidazopyridinyl group, 5 Imidazopyridinyl group, 6—Imidazopyridyl group, 7—Imidazopyridyl group, 8—Imidazopyridyl group Group, 3-pyridyl group, 4 pyridyl group, 1 indolyl group, 2 indolyl group, 3—indolyl group, 4 indolyl group, 5—indolyl group, 6—indolyl group, 7—indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoin
  • the alkylamino group and the arylamino group are groups represented by — ⁇ ⁇ 2 , and examples of X 1 and X 2 are those described for the alkyl group, the halogenated alkyl group, and the aryl group, respectively. Similar examples are given.
  • Examples of the carboxyl-containing group include methyl ester, ethyl ester, and butyester.
  • alkylsilyl group examples include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a butyldimethylsilyl group, and a propyldimethylsilyl group.
  • arylsilyl group examples include a triphenylsilyl group, a phenyldimethylsilyl group, and a t-butyldiphenylsilyl group.
  • Examples of the ring structure formed by crosslinking R 1 and R 2 include the same examples as those given for the heterocyclic group.
  • a ring and B ring may be the same or different, and may be bridged with each other.
  • the compound power represented by the general formula (1) is preferably a transition metal complex compound having a metal carbene bond represented by the following general formula (2).
  • C (carbon atom) ⁇ M represents a metal carbene bond.
  • M and k are the same as described above, m is an integer of 0 to 2, and k + m represents the valence of metal M.
  • alkyl group having 1 to 30 carbon atoms which may have a substituent a halogenated alkyl group having 1 to 30 carbon atoms which may have a substituent, and a substituent.
  • -30 aromatic hydrocarbon group optionally substituted cycloalkyl group having 3 to 30 carbon atoms, cycloalkyl group having 7 to 40 carbon atoms, aralkyl group having 7 to 40 carbon atoms and substituents.
  • L 2 represents a monodentate ligand. j is the same as above, and when j is plural, each L 2 may be the same or different and may be cross-linked. In the general formula (3), L 2 is the same ligand as described above, and the same specific examples can be given.
  • L 3 is a super strong acid having a pKa value of ⁇ 10 or less, Examples include carboxylic acids, aldehydes, ketones, alcohols, thioalcohols, phenols, amines, amides, aromatic or alkane conjugate bases, hydrogen ions, halide ions, and pKa values. — Conjugated bases and halides of super strong acids that are 10 or less are preferred.
  • conjugate bases of super strong acids whose pKa value is -10 or less, SbF-, FSO-, CIO
  • conjugate base of amamines As the conjugate base of amamines, RR 'N—Issue As conjugated bases of amides, RR' NCOR “" isosity Examples of aromatic conjugate bases include (substituted) cyclopentadenyl-one, Ar—, and examples of alkane conjugate bases include Me—, tBu— (Me is methane, Bu is butane), and the like. As halide ions,
  • R ′ and R ′′ include the same examples as R 18 described above.
  • L 3 -L 2 ligands in which L 3 and L 2 are bridged
  • L 3 and L 2 include, for example, conjugate bases of (substituted) acetylethylacetones, conjugate bases of j8 ketoimines Conjugated bases of j8 diimines, conjugated bases of (substituted) picolinic acid, conjugated bases of (substituted) malonic acid diesters, conjugated bases of (substituted) acetoacetic esters, conjugated bases of (substituted) acetoacetamides, (Substituted) conjugate bases of amidinates and the like.
  • Z 1 is a carbon, silicon, nitrogen or phosphorus atom
  • Z 3 and R 1 are the same as those described above, and specific examples are the same.
  • a ring and B ring may be the same or different. It may be, or it may be cross-linked between adjacent ones.
  • C (carbon atom) ⁇ M represents a metal carbene bond
  • a bond indicated by a solid line (-) represents a covalent bond
  • a bond indicated by an arrow ( ⁇ ) represents a coordinate bond.
  • M is the same as described above
  • L 2 represents a monodentate ligand.
  • j is the same as above, and when j is plural, each L 2 may be the same or different and may be cross-linked.
  • L 2 is the same ligand as defined above, L 3 , Zeta 3 and R 1, Ri same der as defined above, a similar embodiment can be mentioned.
  • L 3 - Examples of L 2 include the same examples as (L 3 and L 2 are ligands crosslinked). Also, The A ring and the B ring may be the same or different, and may be bridged with each other.
  • C (carbon atom) ⁇ Ir (iridium) represents a metal carbene bond
  • a bond indicated by a solid line (one) represents a covalent bond
  • an arrow ( ⁇ ) The bond shown by means a coordination bond.
  • L 2 represents a monodentate ligand. j is the same as described above, and when j is plural, each L 2 may be the same or different and may be cross-linked.
  • L 2 is the same ligand as defined above, L 3 , Zeta 3 and R 1, Ri same der as defined above, a similar embodiment can be mentioned.
  • Rings A and B may be the same or different and may be bridged by adjacent ones.
  • the solvent includes (substituted) aromatic hydrocarbons, (substituted) heteroatom-containing aromatics, (substituted) straight chain monoters, (substituted) cyclic cages. Ters, (substituted) cyclic thioethers, (substituted) alcohols, (substituted) aliphatic hydrocarbons, and the like.
  • the (substituted) aromatic hydrocarbon examples include benzene, toluene, xylene, mesitylene, 1,2,3,4-tetrahydronaphthalene, and the (substituted) hetero atom-containing aromatic includes Pyridine derivatives such as pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,6-dimethylpyridine, quinoline, isoquinoline, furan, 2-methyl Examples include furan derivatives such as tilfuran, 3-methylfuran, 2,5 dimethylfuran, and benzofuran, thiophene derivatives such as thiophene, 2-methylthiophene, 3-methylthiophene, 2,5 dimethylthiophene, and benzothiophene.
  • Pyridine derivatives such as pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,6-dimethylpyridine, quinoline, isoquinoline, furan, 2-methyl
  • furan derivatives such as til
  • linear ethers examples include diisopropyl ether, dibutyl ether, and diethylene glycol diethyl ether.
  • (substituted) cyclic ethers include tetrahydrofuran, 2-methyltetrahydrofuran, 3-methyltetrahydrofuran, and 2,5 dimethyltetrahydrofuran.
  • tetrahydrofuran derivatives such as 2, 2, 5, 5-tetramethyltetrahydrofuran
  • (substituted) cyclic thioethers include tetrahydrothiophene, 2-methyltetrahydrothiophene, 3-methyltetrahydride.
  • Examples include tetrahydrothiophene derivatives such as thiophene, 2,5 dimethyltetrahydrothiophene, 2,2,5,5-tetramethyltetrahydrothiophene, and (substituted) alcohols include 2-methoxyethanol, diethyleneglycol , Tetrahydrofurfuryl alcohol, 1,4 butanediol, 1,6 hexanediol, glycerol, etc.
  • (Substituted) aliphatic hydrocarbons include n decane, n dodecane, n-undecane, decalin, etc. It is done.
  • the metal oxide which is is mentioned.
  • the acid conjugate base having an acid dissociation constant (pKa value) of 15 or more and 40 or less include alkoxyadonone, acid amide aon, amide, alkylamido aon, arylamido aon and the like.
  • alkoxy door-on examples include methoxy door-on, ethoxy door-on, etc.
  • acid amido-on examples include benzoic acid amide-on, acetic acid amide-on, and the like.
  • -on examples include methylamido-on and ethylamido-on.
  • aryl-on examples include arylido-on.
  • the metal to be combined with these conjugated bases include lithium cation, sodium cation, potassium cation and magnesium cation.
  • the metal oxide that is a basic oxide examples include magnesium oxide, lithium oxide, acid sodium, acid calcium, copper oxide, and silver oxide. Acid silver is preferred.
  • Examples of the substituent of each group in the general formulas (1) to (7) include a substituted or unsubstituted aryl group having 5 to 50 nuclear carbon atoms and a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
  • Substituted or unsubstituted alkoxy groups having 1 to 50 carbon atoms substituted or unsubstituted aralkyl groups having 6 to 50 nuclear carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 50 nuclear carbon atoms, substituted or unsubstituted Examples thereof include aryloxy groups having 5 to 50 nuclear carbon atoms, substituted or unsubstituted alkoxycarbon groups having 1 to 50 carbon atoms, amino groups, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and carboxyl groups. .
  • an alkyl group having 1 to 10 carbon atoms a cycloalkyl group having 5 to 7 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkyl group having 1 to 6 carbon atoms, and 5 to 7 carbon atoms are preferable.
  • Cycloalkyl groups are more preferred methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, cyclopentyl
  • Particularly preferred is the cyclohexyl group.
  • the organic EL device of the present invention is an organic EL device in which an organic thin film layer comprising at least one light emitting layer or a plurality of layers is sandwiched between a pair of electrodes also having an anode and a cathode force.
  • the content of the metal complex compound of the present invention in the organic thin film layer is usually 0.1 to L00% by weight and preferably 1 to 30% by weight with respect to the total mass of the light emitting layer. .
  • the light emitting layer preferably contains the transition metal complex compound of the present invention as a light emitting material or a dopant.
  • the light emitting layer can be made thin by vacuum deposition or coating. Since the coating process can simplify the manufacturing process, the layer containing the transition metal complex compound of the present invention is formed by coating. This is preferable.
  • the organic EL device of the present invention when the organic thin film layer is of a single layer type, the organic thin film layer is a light emitting layer, and this light emitting layer contains the transition metal complex compound of the present invention. Also many As a layer type organic EL device, (Anode Z Hole injection layer (Hole transport layer) Z Light emitting layer Z Cathode)
  • Electron injection layer (electron transport layer) Z cathode) (Anode Z hole injection layer (hole transport layer) Z light-emitting layer Z electron injection layer (electron transport layer) Z cathode), etc. It is done.
  • the anode of the organic EL device of the present invention supplies holes to a hole injection layer, a hole transport layer, a light emitting layer, and the like, and is effective to have a work function of 4.5 eV or more. is there.
  • a material for the anode a metal, an alloy, a metal oxide, an electrically conductive compound, or a mixture thereof can be used.
  • Specific examples of the material of the anode include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), or metals such as gold, silver, chromium, nickel, and conductive materials thereof. Mixture or laminate of conductive metal oxide and metal
  • Inorganic conductive materials such as copper iodide and copper sulfide, organic conductive materials such as polyarlin, polythiophene and polypyrrole, and laminates of these with ITO, preferably conductive metal oxide
  • ITO inorganic conductive materials
  • the film thickness of the anode can be appropriately selected depending on the material.
  • the cathode of the organic EL device of the present invention supplies electrons to an electron injection layer, an electron transport layer, a light emitting layer, and the like.
  • the cathode material include metals, alloys, metal halides, metal oxides. , Electrically conductive compounds, or mixtures thereof.
  • Specific examples of cathode materials include alkali metals (eg, Li, Na, K, etc.) and their fluorides or oxides, alkaline earth metals (eg, Mg, Ca, etc.), and their fluorides or oxides.
  • aluminum and lithium-aluminum are preferable.
  • the cathode may have a single layer structure of the material or a laminated structure of layers containing the material.
  • a laminated structure of aluminum Z lithium fluoride and aluminum / lithium oxide is preferable.
  • the film thickness of the cathode can be appropriately selected depending on the material.
  • the hole injection layer and the hole transport layer of the organic EL device of the present invention inject holes from the anode. Any one having a function, a function of transporting holes, or a function of blocking the injected electrons from the cathode can be used. Specific examples thereof include strength rubazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine amines, amino substituted chalcone derivatives, styrylanthracene.
  • the hole injection layer and the hole transport layer may have a single layer structure composed of one or more of the materials, or a multilayer structure having a multi-layer force of the same composition or different compositions. It may be.
  • the electron injection layer and the electron transport layer of the organic EL device of the present invention have any one of a function of injecting electrons from the cathode, a function of transporting electrons, and a function of blocking holes injected from the anode. What is necessary is just to have. Specific examples thereof include triazole derivatives, oxazol derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carpositimide derivatives, fluorenylidenemethane derivatives.
  • Metal complexes of aromatic ring tetracarboxylic acid anhydrides such as distyrylvirazine derivatives, naphthalene and perylene, phthalocyanine derivatives, 8-quinolinol derivatives, metal phthalocyanines, metal complexes having benzoxazole and benzothiazole as ligands.
  • Examples include various metal complexes, organosilane derivatives, and transition metal complex compounds of the present invention.
  • the electron injection layer and the electron transport layer may have a single-layer structure composed of one or more of the materials, or a multilayer structure having a multi-layer force of the same composition or different compositions. Moyo.
  • examples of the electron transport material used for the electron injection layer and the electron transport layer include the following compounds.
  • the electron injection layer and the Z or electron transport layer contain a ⁇ electron deficient nitrogen-containing heterocyclic derivative as a main component.
  • a nitrogen-containing 5-membered ring derivative selected from benzimidazole ring, benztriazole ring, pyridinoimidazole ring, pyrimidinoimidazole ring, pyridazinoimidazole ring,
  • a nitrogen-containing 6-membered ring derivative composed of a pyridine ring, a pyrimidine ring, a pyrazine ring, or a triazine ring is preferred.
  • Preferred examples of the nitrogen-containing 6-membered ring derivative include structures represented by the following general formulas C—I, c—n, c—m, C—IV, Ji and Hide- ⁇ , and particularly preferred. Is a structure represented by general formulas CI and C-II. [0072] [Chemical 21]
  • L B represents a divalent or higher linking group, preferably carbon, Keimoto, nitrogen, boron, oxygen, sulfur, metals, a linking group formed like a metal ion More preferably a carbon atom, a nitrogen atom, a carbon atom, a boron atom, an oxygen atom, a sulfur atom, an aromatic hydrocarbon ring or an aromatic heterocycle, and still more preferably a carbon atom, a carbon atom or an aromatic. It is a hydrocarbon ring or an aromatic hetero ring.
  • L B is preferably an alkyl group as Yogu substituent may have a substituent, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, an amino group, an alkoxy group, Ariruokishi group, ⁇ sill group, an alkoxy Carbon group, aryloxycarbol group, acyloxy group, acylamino group, alkoxy carbolumino group, aryloxycarbolamino group, sulfo-lumino group, sulfamoyl group, rubamoyl group, alkylthio Group, aryl group, sulfonyl group, halogen atom, cyano group and aromatic heterocyclic group, more preferably alkyl group, aryl group, alkoxy group, aryloxy group, halogen atom, cyan group and aromatic heterocyclic group.
  • an alkyl group More preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or an aromatic heterocyclic group. Particularly preferably an alkyl group, Ariru group, an alkoxy group, an aromatic heterocyclic group.
  • [0074] include those of the following specific examples of the linking group represented by L B.
  • R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group, or a heterocyclic group.
  • the aliphatic hydrocarbon group represented by R B2 is a linear, branched or cyclic alkyl group (preferably an alkyl group having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms).
  • alkyl group preferably an alkyl group having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, particularly preferably 1 to 8 carbon atoms.
  • a alkenyl group (preferably a alkenyl group having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms. Group, 2-buture group, 3-pentane group, etc.), alkyl group (preferably having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms).
  • Alkynyl groups such as propargyl group, 3-pentynyl Etc. can be mentioned, et al are.), More preferably an alkyl group.
  • the aryl group represented by R B2 is a monocyclic or condensed aryl group, preferably having 6 to 6 carbon atoms. 30, more preferably an aryl group having 6 to 20 carbon atoms, and still more preferably 6 to 12 carbon atoms, such as a phenyl group, a 2-methylphenol group, a 3-methylphenol group, a 4-methylphenol group, Examples include 2-methoxyphenyl group, 3-trifluoromethylphenol group, pentafluorophenyl group, 1-naphthyl group, 2-naphthyl group.
  • the heterocyclic group represented by R B2 is a monocyclic or condensed heterocyclic group (preferably having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and further preferably 2 to 10 carbon atoms).
  • Heteroaromatic group preferably an aromatic heterocyclic group containing at least one of a nitrogen atom, an oxygen atom, a sulfur atom, and a selenium atom, such as pyrrolidine, piperidine, piperazine, Morpholine, thiophene, selenophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, Isoquinoline, phthalazine
  • Aliphatic hydrocarbon group represented by R B2 Ariru group, heterocyclic group include the same device it may also have a substituent wherein L B.
  • Z B2 represents an atomic group necessary for forming an aromatic ring.
  • the aromatic ring formed by Z B2 is Specific examples of the aromatic hydrocarbon ring and the aromatic heterocycle include, for example, a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, a pyrrole ring, a furan ring, and a thiophene ring.
  • Selenophene ring, terorophene ring, imidazole ring, thiazole ring, selenazole ring, tellurazole ring, thiadiazole ring, oxadiazole ring, pyrazole ring, etc. preferably benzene ring, pyridine ring, pyrazine ring, pyrimidine ring, A pyridazine ring, more preferably a benzene ring, a pyridine ring, or a pyrazine ring.
  • the aromatic ring formed by z B 2 may further form a condensed ring with another ring or may have a substituent.
  • a substituent preferably an alkyl group, an alkyl group, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonyl group, an arylcarbonyl group, an acyloxy group.
  • acylamino group alkoxy carbo-lumino group, aryloxy carbo-lumino group, sulfo-lumino group, sulfamoyl group, strong rubamoyl group, alkylthio group, arylothio group, sulfol group, halogen atom, cyano group
  • a heterocyclic group more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, a halogen atom, a cyano group, or a heterocyclic group, and even more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group.
  • aromatic heterocyclic group particularly preferably alkyl group, aryl group, alkoxy group.
  • Ru heterocyclic group der aromatic.
  • n B2 is an integer of 1 to 4, preferably 2 to 3.
  • R B71 , R B72 and R B73 are the same as R B2 in general formula (BI), respectively, and the preferred ranges are also the same.
  • Z B72 and Zeta Beta73 are similar to Zeta B2 in the general formula (Beta iota) respectively, also are similar ranges have preferred.
  • L B71, L B72 and L B73 each represent a linking group
  • the general formula (B- I) can be mentioned those divalent examples of L B in, preferably, a single bond, a divalent aromatic hydrocarbon A hydrogen ring group, a divalent aromatic heterocyclic group, and a linking group having a combination force thereof, more preferably a single bond.
  • L m , L B72 and L B73 may have a substituent. Examples of the substituent may be the same as L B in the general formula (BI).
  • Y represents a nitrogen atom, a 1, 3, 5-benzenetriyl group or a 2, 4, 6-triazine triyl group.
  • the 1, 3, 5-benzenetriyl group may have a substituent at the 2, 4, 6-position, and examples thereof include an alkyl group, an aromatic hydrocarbon ring group, and a halogen atom. It is possible.
  • Cz is a substituted or unsubstituted carbazolyl group, aryl carbazolyl group or force rubazolylalkylene group
  • A is a group formed from a site represented by the following general formula (A).
  • n and m are integers from 1 to 3, respectively.
  • M and M ′ are each independently a nitrogen-containing heteroaromatic ring having 2 to 40 carbon atoms to form a ring, and the ring may or may not have a substituent.
  • M and M ' Can be the same or different.
  • L is a single bond, an arylene group having 6 to 30 carbon atoms, a cycloalkylene group having 5 to 30 carbon atoms, or a heteroaromatic ring having 2 to 30 carbon atoms, and having a substituent bonded to the ring. May not be included.
  • p is an integer from 0 to 2
  • q is an integer from 1 to 2
  • r is an integer from 0 to 2. However, p + r is 1 or more.
  • the bonding mode of the group represented by the general formula (A) depends on the number of parameters p, q, r, specifically, the forms described in (1) to (16) in the following table. It is.
  • Ar to Ar each represent the same group as R B2 in the general formula (B—I), and specific examples thereof are also the same.
  • Ar to Ar represent divalent groups similar to R B2 in the general formula (B—I).
  • the example is similar. )
  • R to R each represent the same group as R B2 in the general formula (B—I), and specific examples thereof are also the same.
  • an insulator or a semiconductor inorganic compound as a substance constituting the electron injection / transport layer.
  • the electron injection / transport layer is composed of an insulator or a semiconductor, current leakage can be effectively prevented and electron injection can be improved.
  • an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkali earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides. . If the electron injecting / transporting layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injecting property can be further improved.
  • alkali metal chalcogenides include, for example, Li 0, LiO, Na
  • alkaline earth metal chalcogenides include
  • alkali metal halide examples include LiF, NaF, KF, LiCl, KC1, and NaCl.
  • alkaline earth metal halides examples include fluorides such as Ca F, BaF, SrF, MgF and BeF, and halides other than fluorides.
  • the electron injection 'transport layer at least one of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb and Zn is used.
  • the inorganic compound constituting the electron transport layer is preferably a microcrystalline or amorphous insulating thin film. If the electron transport layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include the alkali metal chalcogenides and alkaline earths described above. Metal halide chalcogenides, alkali metal halides and alkaline earth metal halides.
  • the electron injection layer and / or the electron transport layer may contain a reducing dopant having a work function of 2.9 eV or less.
  • the reducing dopant is a compound that increases the electron injection efficiency.
  • reducing dopants include alkali metal, alkaline earth metal oxide, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkaline earth metal oxide, alkali It is at least one compound selected from the group consisting of earth metal halides, rare earth metal oxides or rare earth metal halides, alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes.
  • preferred reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV) and Cs (work function: 1 95eV) Force Group Force At least one selected alkali metal, Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV) and Ba (work function: 2.52 eV) Powerful group power At least one alkaline earth metal selected is mentioned, and a work function of 2.9 eV is particularly preferred.
  • a more preferable reducing dopant is at least one alkali metal selected from the group consisting of K, Rb, and Cs, more preferably Rb or Cs, and most preferably Cs. .
  • These alkali metals can improve emission brightness and extend the life of organic EL devices by adding a relatively small amount to the electron injection region, which has a particularly high reducing ability.
  • alkaline earth metal oxides examples include BaO, SrO, CaO and Ba Sr O (0 ⁇ x ⁇ 1) mixed with these and Ba Ca O (0 ⁇ x ⁇ 1). are listed as preferred
  • alkali oxides or alkali fluorides include LiF, Li 0, and NaF.
  • the alkali metal complex, alkaline earth metal complex, and rare earth metal complex are not particularly limited as long as they contain at least one of alkali metal ions, alkaline earth metal ions, and rare earth metal ions as metal ions.
  • the ligand include quino Linol, benzoquinolinol, attaridinol, phenanthridinol, hydroxyphenyl thiazole, hydroxyphenyl thiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylvinylidine, hydroxyphenylbenzo Imidazole, hydroxybenzotriazole, hydroxyfulborane, bipyridyl
  • the reducing dopant is formed in a layer shape or an island shape.
  • the preferred film thickness is 0.05 to 8 nm.
  • an organic substance that is a light-emitting material or an electron injecting material that forms an interface region is simultaneously deposited while a reducing dopant is deposited by resistance heating vapor deposition.
  • a method in which a reducing dopant is dispersed therein is preferred.
  • the dispersion concentration is 100: 1 to 1: 100, preferably 5: 1 to 1: 5, as a molar ratio.
  • the reducing dopant is vapor-deposited by resistance heating evaporation method, preferably 0.05 to ln. Form with m.
  • the light emitting layer of the organic EL device of the present invention can inject holes from the anode or the hole injection layer when an electric field is applied, and can inject electrons from the cathode or the electron injection layer. It provides a function to move the generated charges (electrons and holes) by the force of an electric field, a field for recombination of electrons and holes, and a function to connect this to light emission.
  • the light emitting layer of the organic EL device of the present invention may contain a host material using the transition metal complex compound as a guest material, which preferably contains at least the transition metal complex compound of the present invention.
  • Examples of the host material include those having a force rubazole skeleton, those having a diarylamine skeleton, those having a pyridine skeleton, those having a pyrazine skeleton, those having a triazine skeleton, and those having an allylsilane skeleton. . T1 (minimum triple) of the host material
  • the energy level of the excited state is preferably greater than the T1 level of the guest material.
  • the host material may be a low molecular compound or a high molecular compound.
  • the light emitting material such as the transition metal complex compound
  • a method for forming each layer is not particularly limited, but a vacuum deposition method, an LB method, a resistance heating deposition method, an electron beam method, a sputtering method, a molecular lamination method, a coating method, and the like.
  • Various methods such as a spin coating method, a casting method, a dip coating method, an ink jet method, and a printing method can be used.
  • a coating method that is a coating method is preferred.
  • the organic thin film layer containing the transition metal complex compound of the present invention can be prepared by vacuum deposition, molecular beam deposition (MBE), solution dating, solvent coating, spin coating, casting, bar coating. It can be formed by a known method using a coating method such as a coating method or a roll coating method.
  • MBE molecular beam deposition
  • the coating method can be formed by dissolving the transition metal complex compound of the present invention in a solvent to prepare a coating solution, and coating and drying the coating solution on a desired layer (or electrode). .
  • rosin which may contain rosin can be dissolved in a solvent or dispersed.
  • a non-conjugated polymer for example, polyvinyl carbazole
  • a conjugated polymer for example, a polyolefin polymer
  • each organic layer of the organic EL element of the present invention is not particularly limited. In general, however, if the film thickness is too thin, defects such as pinholes are generated. Usually, the range of several nm to 1 ⁇ m is preferable because of worsening.
  • Compound b was synthesized using compound a synthesized in (i) above. In the presence of Sichus, 2.82 g (0.0153 monole) of compound a and 2.90 milliliters of formic acid (0.007 65 mol, 5 equivalents) were added and stirred at 95 ° C for 4 hours. Was done. This was cooled to room temperature, 100 ml of water was removed, and extraction was performed with methylene chloride (5 times each in 50 ml). Magnesium sulfate was added to this solution for dehydration, the solid component was filtered off, and the solvent was distilled off under reduced pressure to obtain a brown oil.
  • Compound c was synthesized using compound b synthesized in (ii) above.
  • Compound B (1.03 g, 4.85 millimonoles), aged salted salt, 0.50 milliliter Nore (5.34 millimonoles), and 10 milliliters of toluene at 80 ° C for 12 hours.
  • This solution was distilled off under reduced pressure to obtain 1.97 g of a greenish gray solid as a crude product.
  • 40 ml of methylene chloride was added to 0.602 g of this crude product, and after sufficient stirring, solid components were removed using a centrifugal separator to obtain a greenish brown solution.
  • Compound 1 was synthesized through the following reaction steps.
  • Compound 1 was synthesized through the following reaction steps.
  • Compound 1 was synthesized through the following reaction steps.
  • Compound 2 was synthesized by the following reaction process.
  • Compound 3 was synthesized in the following reaction process.
  • Compound 4 was synthesized by the following reaction process.
  • the measurement conditions of FD-MS measurement were as follows.
  • Cyclic voltammetry was measured under the following conditions.
  • HV HV
  • 5 100 electrochemical instruments (HoKuto DenKo corp.), LOOmVZs scan rate of 0.001M compound 4 and 0.1M TBAPF [hexa
  • the transition metal complex compound having a metal carbene bond of the present invention has an electroluminescence property, has high luminous efficiency, and can provide an organic EL device. Moreover, according to the method for producing a transition metal complex compound of the present invention, a transition metal complex compound can be produced efficiently.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé complexe de métal de transition avec une structure spécifique ayant une liaison carbène ; et son procédé de production. La présente invention concerne un dispositif électroluminescent organique comprenant une électrode positive et une électrode négative et, interposées entre celles-ci, une, deux ou plusieurs couches de film mince organique comprenant au moins une couche luminescente, au moins une des couches de film mince organique contient le composé complexe de métal de transition ayant une liaison métal carbène. Le nouveau composé complexe de métal de transition proposé avec une liaison carbène présente des propriétés d’électroluminescence et peut proposer un dispositif électroluminescent organique de rendement lumineux élevé, et la présente invention concerne le procédé de production du composé complexe de métal de transition.
PCT/JP2006/322852 2005-11-17 2006-11-16 Compose complexe de metal de transition WO2007058255A1 (fr)

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US11/516,759 US20080233410A1 (en) 2005-11-17 2006-09-07 Transition metal complex compound

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009532549A (ja) * 2006-04-04 2009-09-10 ビーエーエスエフ ソシエタス・ヨーロピア １つの非カルベン配位子と１もしくは２つのカルベン配位子を有する遷移金属錯体並びにｏｌｅｄにおけるその使用
CN101787542A (zh) * 2010-03-16 2010-07-28 浙江大学 金属氮杂环卡宾配合物的电化学合成方法
WO2012046715A1 (fr) * 2010-10-06 2012-04-12 シャープ株式会社 Matière luminescente et élément électroluminescent organique, élément électroluminescent convertisseur de longueur d'onde, élément électroluminescent convertisseur de lumière, élément électroluminescent à diode laser organique, laser à colorant, dispositif d'affichage et dispositif d'éclairage utilisant ceux-ci
WO2012046714A1 (fr) * 2010-10-06 2012-04-12 シャープ株式会社 Matière luminescente et élément électroluminescent organique, élément électroluminescent convertisseur de longueur d'onde, élément électroluminescent convertisseur de lumière, élément électroluminescent à diode laser organique, laser à colorant, dispositif d'affichage et dispositif d'éclairage utilisant ceux-ci
US8377332B2 (en) 2008-06-10 2013-02-19 Basf Se Transition metal complexes and use thereof in organic light emitting diodes—III
US8410270B2 (en) 2008-06-10 2013-04-02 Basf Se Transition metal complexes and use thereof in organic light-emitting diodes V
US8492749B2 (en) 2004-12-23 2013-07-23 Basf Se Electroluminescent metal complexes with nucleophilic carbene ligands
JP2014170820A (ja) * 2013-03-04 2014-09-18 Konica Minolta Inc 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
US8859110B2 (en) 2008-06-20 2014-10-14 Basf Se Cyclic phosphazene compounds and use thereof in organic light emitting diodes
CN105859790A (zh) * 2016-04-07 2016-08-17 瑞声光电科技(常州)有限公司 铱配合物及其制备方法和应用铱配合物的电致发光器件
CN106084188A (zh) * 2016-06-23 2016-11-09 福建师范大学 一种咪唑基多孔有机离子聚合物的制备方法
WO2018236199A1 (fr) * 2017-06-23 2018-12-27 광주과학기술원 Ligand pour former un complexe de cuivre, ligand pour former un complexe de palladium, catalyseur de complexe de cuivre, catalyseur de complexe de palladium, procédé de production et utilisation associés
KR20190107264A (ko) * 2018-03-09 2019-09-19 삼성디스플레이 주식회사 유기금속 화합물 및 이를 포함한 유기 발광 소자
EP3978583A1 (fr) * 2020-10-02 2022-04-06 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005019373A2 (fr) * 2003-08-19 2005-03-03 Basf Aktiengesellschaft Complexes de metal de transition comportant des ligands de carbene faisant office d'emetteurs pour diodes electroluminescentes organiques (delo)

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005019373A2 (fr) * 2003-08-19 2005-03-03 Basf Aktiengesellschaft Complexes de metal de transition comportant des ligands de carbene faisant office d'emetteurs pour diodes electroluminescentes organiques (delo)

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ALCARAZO M. ET AL.: "Imidazo[1,5-a]pyridine: A Versatile Architecture for Stable N-Heterocyclic Carbenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 127, no. 10, 2005, pages 3290 - 3291, XP003009080 *
BURSTEIN C. ET AL.: "Imidazo[1,5-a]pyridine-3-ylidenes-pyridine derived N-heterocyclic carbene ligands", TETRAHEDRON, vol. 61, no. 26, 2005, pages 6207 - 6217, XP004923085 *

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US9012899B2 (en) 2004-12-23 2015-04-21 Basf Se Electroluminescent metal complexes with nucleophilic carbene ligands
US8492749B2 (en) 2004-12-23 2013-07-23 Basf Se Electroluminescent metal complexes with nucleophilic carbene ligands
JP2009532549A (ja) * 2006-04-04 2009-09-10 ビーエーエスエフ ソシエタス・ヨーロピア １つの非カルベン配位子と１もしくは２つのカルベン配位子を有する遷移金属錯体並びにｏｌｅｄにおけるその使用
US8377332B2 (en) 2008-06-10 2013-02-19 Basf Se Transition metal complexes and use thereof in organic light emitting diodes—III
US8410270B2 (en) 2008-06-10 2013-04-02 Basf Se Transition metal complexes and use thereof in organic light-emitting diodes V
US8592586B2 (en) 2008-06-10 2013-11-26 Basf Se Transition metal complexes and use thereof in organic light-emitting diodes V
US8859110B2 (en) 2008-06-20 2014-10-14 Basf Se Cyclic phosphazene compounds and use thereof in organic light emitting diodes
CN101787542A (zh) * 2010-03-16 2010-07-28 浙江大学 金属氮杂环卡宾配合物的电化学合成方法
WO2012046715A1 (fr) * 2010-10-06 2012-04-12 シャープ株式会社 Matière luminescente et élément électroluminescent organique, élément électroluminescent convertisseur de longueur d'onde, élément électroluminescent convertisseur de lumière, élément électroluminescent à diode laser organique, laser à colorant, dispositif d'affichage et dispositif d'éclairage utilisant ceux-ci
WO2012046714A1 (fr) * 2010-10-06 2012-04-12 シャープ株式会社 Matière luminescente et élément électroluminescent organique, élément électroluminescent convertisseur de longueur d'onde, élément électroluminescent convertisseur de lumière, élément électroluminescent à diode laser organique, laser à colorant, dispositif d'affichage et dispositif d'éclairage utilisant ceux-ci
JP2014170820A (ja) * 2013-03-04 2014-09-18 Konica Minolta Inc 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
CN105859790A (zh) * 2016-04-07 2016-08-17 瑞声光电科技(常州)有限公司 铱配合物及其制备方法和应用铱配合物的电致发光器件
CN106084188A (zh) * 2016-06-23 2016-11-09 福建师范大学 一种咪唑基多孔有机离子聚合物的制备方法
WO2018236199A1 (fr) * 2017-06-23 2018-12-27 광주과학기술원 Ligand pour former un complexe de cuivre, ligand pour former un complexe de palladium, catalyseur de complexe de cuivre, catalyseur de complexe de palladium, procédé de production et utilisation associés
KR20190107264A (ko) * 2018-03-09 2019-09-19 삼성디스플레이 주식회사 유기금속 화합물 및 이를 포함한 유기 발광 소자
KR102654922B1 (ko) * 2018-03-09 2024-04-05 삼성디스플레이 주식회사 유기금속 화합물 및 이를 포함한 유기 발광 소자
EP3978583A1 (fr) * 2020-10-02 2022-04-06 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4358685A3 (fr) * 2020-10-02 2024-07-10 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs

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