WO2013031794A1 - Élément électroluminescent organique, dispositif d'affichage, et dispositif d'éclairage - Google Patents

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

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WO2013031794A1
WO2013031794A1 PCT/JP2012/071762 JP2012071762W WO2013031794A1 WO 2013031794 A1 WO2013031794 A1 WO 2013031794A1 JP 2012071762 W JP2012071762 W JP 2012071762W WO 2013031794 A1 WO2013031794 A1 WO 2013031794A1
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ring
organic
aromatic hydrocarbon
hydrocarbon ring
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西関　雅人
加藤　栄作
大野　香織
三浦　紀生
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コニカミノルタホールディングス株式会社
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Definitions

  • the present invention relates to an organic electroluminescence element, a display device, and a lighting device.
  • ELD electroluminescence display
  • the constituent elements of ELD include inorganic electroluminescent elements and organic electroluminescent elements (hereinafter also referred to as organic EL elements).
  • Inorganic electroluminescent elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements.
  • an organic EL device has a structure in which a light-emitting layer containing a light-emitting compound is sandwiched between a cathode and an anode, and excitons (excitons) are generated by injecting electrons and holes into the light-emitting layer and recombining them.
  • Japanese Patent No. 3093796 discloses a technique for doping a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative with a trace amount of a phosphor to improve emission luminance and extend the lifetime of the device. It is disclosed. Further, an element having an organic light-emitting layer in which 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of phosphor is doped to the host compound (for example, Japanese Patent Laid-Open No. 63-264692), 8-hydroxyquinoline aluminum complex is used as a host compound. For example, an element having an organic light emitting layer doped with a quinacridone dye (for example, JP-A-3-255190) is known.
  • a quinacridone dye for example, JP-A-3-255190
  • the limit of the external extraction quantum efficiency ( ⁇ ) is set to 5%.
  • ortho-metalated complexes in which the central metal of the iridium complex is platinum are attracting attention.
  • many examples are known in which ligands are characterized.
  • the light emission luminance and light emission efficiency of the light emitting device are greatly improved compared to conventional devices because the emitted light is derived from phosphorescence.
  • phosphorescent high-efficiency light-emitting materials are difficult to improve the light emission life of the device, and it is difficult to shorten the emission wavelength, and the performance that can withstand practical use cannot be sufficiently achieved.
  • a metal complex having phenylpyrazole as a ligand is a light-emitting material having a short emission wavelength (see, for example, Patent Document 1). Further, it is disclosed that a metal complex having phenylimidazole as a ligand is also a light emitting material having a short emission wavelength (see, for example, Patent Documents 2, 3, and 4). Furthermore, there is a disclosure of a metal complex that is a condensed aromatic heterocyclic ligand of an 18 ⁇ electron system such as a phenanthridine skeleton (see, for example, Patent Documents 5 and 6).
  • the reason why the luminous efficiency in the high-luminance emission region decreases in the conventional device configuration is that the doping amount of the phosphorescent dopant in the light emitting layer is insufficient with respect to the current, and the doping amount of the dopant is increased. Although the luminous efficiency can be improved, this method cannot simultaneously improve the luminous lifetime.
  • a main object of the present invention is to provide an organic EL element, an illumination device, and a display device using an organic EL element material that exhibits high light emission efficiency in a high luminance light emission region (over 2000 cd / m 2 ) and has a long light emission lifetime. Is to provide. Furthermore, another object of the present invention is to provide an organic EL element material that exhibits high luminous efficiency, has a low driving voltage, and has a long emission lifetime in white light emission, and productivity of such an organic EL element material. Is to provide a high wet process.
  • Organic electroluminescence characterized in that at least one layer of the organic layer contains a phosphorescent organometallic complex in which a ligand represented by the general formula (1) is coordinated to a metal atom. An element is provided.
  • ring A, ring B and ring C represent a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle, and Z represents CH or N.
  • Cy represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocycle, non-aromatic hydrocarbon ring or non-aromatic heterocycle.
  • R1 and R2 are each independently a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a cycloalkyloxy group, an amino group, a silyl group, An arylalkyl group, an aryl group, a heteroaryl group, an aryloxy group, a heteroaryloxy group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group.
  • Ra, Rb and Rc are each independently a hydrogen atom, halogen atom, cyano group, optionally substituted alkyl group, cycloalkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group Represents an aryl group, a heteroaryl group, an aryloxy group, a heteroaryloxy group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, na and nc represent 1 or 2, and nb represents 1 to 3 Represents an integer.
  • R is a halogen atom, a cyano group, an optionally substituted alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, an aryloxy group Represents a heteroaryloxy group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and n0 represents an integer of 1 to 5.
  • Ra, Rb, Rc and R may be the same or different from each other.
  • an organic EL element that exhibits high light emission efficiency in a high-luminance light emission region (over 2000 cd / m 2 ), has a low driving voltage, and has a long light emission lifetime. Further, as a result of the study by the inventors, the present invention can greatly reduce the initial deterioration at the start of element driving, and further reduce the occurrence of dark spots in the light emitting element during element driving. Successful and useful organic EL devices can be provided. In addition, it is possible to provide a highly efficient white light-emitting illumination device and a white light-emitting light source for a display device using the element. Furthermore, an organic EL element material useful for an organic EL element using a highly productive wet process can be obtained.
  • the blue light emitting layer preferably has an emission maximum wavelength of 430 nm to 480 nm
  • the green light emitting layer has an emission maximum wavelength of 510 nm to 550 nm
  • the red light emitting layer has an emission maximum wavelength of 600 nm to 640 nm.
  • a monochromatic light emitting layer in the range is preferable, and the display device of the present invention is preferably configured using such an organic EL element.
  • the organic EL element may be a white light emitting layer formed by laminating at least three light emitting layers. Further, a non-light emitting intermediate layer may be provided between the light emitting layers.
  • the organic EL element of the present invention is preferably a white light emitting layer, and the lighting device of the present invention is preferably configured using these.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.
  • the total film thickness of the light emitting layer is not particularly limited, but from the viewpoint of improving the uniformity of the film, preventing unnecessary application of high voltage during light emission, and improving the stability of the emission color with respect to the drive current. It is preferably adjusted to a range of 2 nm to 5 ⁇ m, more preferably adjusted to a range of 2 nm to 200 nm, and particularly preferably adjusted to a range of 10 nm to 20 nm.
  • a light emitting dopant or a host compound which will be described later, is formed by a known thinning method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink jet method. it can.
  • the light emitting layer of the organic EL device of the present invention preferably contains a light emitting host compound and at least one kind of light emitting dopant (such as a phosphorescent dopant (also referred to as a phosphorescent dopant) or a fluorescent dopant).
  • a light emitting host compound such as a phosphorescent dopant (also referred to as a phosphorescent dopant) or a fluorescent dopant).
  • Host compound also referred to as light-emitting host
  • the host compound used in the present invention will be described.
  • the host compound has a mass ratio of 20% or more among the compounds contained in the light emitting layer, and has a phosphorescence quantum yield of phosphorescence of 0 at room temperature (25 ° C.). Defined as less than 1 compound.
  • the phosphorescence quantum yield is preferably less than 0.01.
  • the host compound one kind of known host compound may be used alone, or a plurality of kinds may be used in combination. By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the efficiency of the organic EL element can be further increased. Moreover, it becomes possible to mix different light emission by using multiple types of light emission dopants mentioned later, and, thereby, arbitrary luminescent colors can be obtained.
  • 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 vinyl group or an epoxy group (evaporation polymerizable light emitting host). Alternatively, one or a plurality of such compounds may be used.
  • a compound having a hole transporting ability and an electron transporting ability, that prevents the emission of light from becoming longer in wavelength, and has a high Tg (glass transition temperature) is preferable.
  • a fluorescent dopant also referred to as a fluorescent compound
  • a phosphorescent dopant also referred to as a phosphorescent emitter, a phosphorescent compound, a phosphorescent compound, or the like
  • the light emitting dopant used in the light emitting layer or the light emitting unit of the organic EL device of the present invention (sometimes simply referred to as a light emitting material) contains the above host compound. At the same time, it is preferable to contain a phosphorescent dopant.
  • the phosphorescent dopant according to the present invention is a compound in which light emission from an excited triplet is observed.
  • the phosphorescent dopant is a compound that emits phosphorescence at room temperature (25 ° C.) and has a phosphorescence quantum yield of 25. Although it is defined as a compound of 0.01 or more at ° C., a preferable phosphorescence quantum yield is 0.1 or more.
  • the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of Experimental Chemistry Course 4 of the 4th edition. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence dopant according to the present invention achieves the phosphorescence quantum yield (0.01 or more) in any solvent. That's fine.
  • the energy transfer type that obtains light emission from the phosphorescent dopant, and the other is that the phosphorescent dopant becomes a carrier trap, carrier recombination occurs on the phosphorescent dopant, and light emission from the phosphorescent dopant is obtained.
  • the excited state energy of the phosphorescent dopant is required to be lower than the excited state energy of the host compound.
  • the phosphorescent dopant according to the present invention is preferably a complex compound containing a group 8-10 metal in the periodic table of elements, more preferably an iridium compound, an osmium compound, or a platinum compound (platinum complex compound), Rare earth complexes, most preferably iridium compounds.
  • an organic compound having a ligand (also referred to as a ligand compound) represented by the following general formula (1) or general formula (1-1): Metal complexes and organometallic complexes represented by general formula (2), general formula (2-1), or general formula (3) are used.
  • a ligand compound also referred to as a ligand compound
  • Metal complexes and organometallic complexes represented by general formula (2), general formula (2-1), or general formula (3) are used.
  • Organometallic complex also called metal complex compound
  • the organometallic complex according to the present invention will be described.
  • the present inventors paid attention to the organic EL element material used for the light emitting layer of the organic EL element, and examined various organometallic complexes used as a light emitting dopant.
  • the present inventors By introducing a specific substituent into the basic skeleton of the organometallic complex, the present inventors suppress the interaction of excitons of the luminescent dopant that causes a decrease in luminous efficiency, and excess electrons or Various complexes were studied under the focus of improving the lifetime degradation due to hole injection.
  • excitons are generated by recombination of charges on an organometallic complex while suppressing the injection of excessive electrons or holes into the light-emitting dopant by introducing the specific substituent disclosed in the present invention. Further, by suppressing the interaction of excitons of the light emitting dopant, the light emission efficiency was improved, and at the same time, the light emission lifetime of the light emitting element could be extended.
  • the initial deterioration at the start of element driving can be greatly reduced, and further, the dark spot of the light emitting element has been greatly reduced, and a useful organic EL element is provided. I was able to.
  • the transition metal complex compound represented by general formula (2), general formula (2-1), or general formula (3) according to the present invention has a plurality of arrangements depending on the valence of the transition metal element represented by M.
  • the ligand can have a ligand, all of the ligands may be the same or may have ligands having different structures.
  • one organometallic complex is preferably composed of 1 to 2 types of ligands, more preferably 1 type of ligand.
  • ligands include various known ligands.
  • Nitrogen heterocyclic ligands for example, bipyridyl, phenanthroline, etc.
  • diketone ligands for example, bipyridyl, phenanthroline, etc.
  • a metal used for forming a functional organometallic complex also referred to as a metal complex or a metal complex compound
  • a transition metal element belonging to Group 8 to 10 in the periodic table of elements also simply referred to as a transition metal, specifically Ru, Rh
  • Pd, Os, Ir, and Pt. is a preferred transition metal element.
  • Organometallic Complex Content Layer According to the Present Invention
  • the efficiency of external extraction quantum efficiency of the organic EL device of the present invention is increased (higher brightness) by using it as a light emitting dopant in the light emitting layer. In addition, it is possible to achieve a longer light emission lifetime.
  • ring A, ring B and ring C represent a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle, and Z represents CH. Or represents N.
  • Benzene ring as 6-membered aromatic hydrocarbon ring, furan ring, thiophene ring, oxazole ring, pyrrole ring, imidazole ring, thiazole ring, etc. as 6-membered aromatic heterocyclic ring, pyridine as 6-membered aromatic heterocyclic ring Ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring and the like.
  • Cy represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocycle, non-aromatic hydrocarbon ring or non-aromatic heterocycle.
  • the 6-membered aromatic hydrocarbon ring is a benzene ring
  • the 5-membered aromatic heterocycle is an oxazole ring, thiazole ring, oxadiazole ring, oxatriazole ring, isoxazole ring, tetrazole ring, thiadiazole ring, thiatriazole ring
  • 6-membered aromatic heterocycles such as isothiazole ring, thiophene ring, furan ring, pyrrole ring, imidazole ring, pyrazole ring, triazole ring, tetrazole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, etc.
  • Examples of the 5-membered non-aromatic hydrocarbon ring include cyclopentane ring and cyclopentene ring
  • examples of the 6-membered non-aromatic hydrocarbon ring include cyclohexane ring, cyclohexene ring, 1,2,3,4-tetrahydronaphthalene ring, 9,9 , 10,10-Tetramethyl-9,10-dihydroanthra 5-membered non-aromatic heterocycle such as pyrrolidine ring, imidazolidine ring, oxazolidine ring, etc., 6-membered non-aromatic heterocycle such as piperidine ring, piperazine ring, morpholyl ring, thiomorpholine ring, tetrahydrofuran ring, And 10H-phenoxazine ring, phenoxathiin ring, chroman-2-one ring, 2,3,4,9-tetrahydro-1H-carbazole
  • R1 and R2 are each independently a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl group (eg, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group) , An octyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, or the like, or a hydrogen atom of these alkyl groups substituted, a cycloalkyl group (for example, a cyclopentyl group, a cyclohexyl group, etc.), an alkenyl group ( For example, vinyl group, allyl group, etc.), alkynyl group (for example, ethynyl group, propargyl group, etc.), alkoxy group (for example, meth
  • Ra, Rb and Rc are each independently a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group (for example, 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 or the like, or a hydrogen atom of these alkyl groups substituted, a cycloalkyl group (for example, a cyclopentyl group, a cyclohexyl group, etc.), an alkenyl Group (for example, vinyl group, allyl group, etc.), alkynyl group (for example, ethynyl group, propargyl group, etc.), al
  • Na and nc represent 1 or 2, and nb represents an integer of 1 to 3.
  • R represents a halogen atom, a cyano group, or an optionally substituted alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group) , Tetradecyl group, pentadecyl group, etc., or those in which hydrogen atoms of these alkyl groups are substituted), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (eg, vinyl group, allyl group, etc.) Alkynyl group (eg, ethynyl group, propargyl group, etc.), alkoxy group (eg, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy
  • Ligand Compound Represented by General Formula (1-1) The ligand compound represented by the general formula (1-1) according to the present invention will be described. Among the ligand compounds represented by the general formula (1) according to the present invention, the ligand compound represented by the general formula (1-1) is preferable.
  • ring A, ring B and ring C represent a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle
  • Z represents CH or N Represents.
  • the 6-membered aromatic hydrocarbon ring is a benzene ring
  • the 5-membered aromatic heterocycle is a 6-membered aromatic heterocycle such as a furan ring, a thiophene ring, an oxazole ring, a pyrrole ring, an imidazole ring, an oxazole ring, or a thiazole ring.
  • Examples thereof include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring.
  • Cy represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocycle, non-aromatic hydrocarbon ring or non-aromatic heterocycle.
  • the 6-membered aromatic hydrocarbon ring is a benzene ring
  • the 5-membered aromatic heterocycle is an oxazole ring, thiazole ring, oxadiazole ring, oxatriazole ring, isoxazole ring, tetrazole ring, thiadiazole ring, thiatriazole ring
  • 6-membered aromatic heterocycles such as isothiazole ring, thiophene ring, furan ring, pyrrole ring, imidazole ring, pyrazole ring, triazole ring, tetrazole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, etc.
  • Examples of the 5-membered non-aromatic hydrocarbon ring include cyclopentane ring and cyclopentene ring
  • examples of the 6-membered non-aromatic hydrocarbon ring include cyclohexane ring, cyclohexene ring, 1,2,3,4-tetrahydronaphthalene ring, 9,9 , 10,10-Tetramethyl-9,10-dihydroanthra 5-membered non-aromatic heterocycle such as pyrrolidine ring, imidazolidine ring, oxazolidine ring, etc., 6-membered non-aromatic heterocycle such as piperidine ring, piperazine ring, morpholyl ring, thiomorpholine ring, tetrahydrofuran ring, And 10H-phenoxazine ring, phenoxathiin ring, chroman-2-one ring, 2,3,4,9-tetrahydro-1H-carbazole
  • R1, R2, R3 and R4 are each independently a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl group (for example, 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, etc., or a hydrogen atom of these alkyl groups substituted, a cycloalkyl group (for example, a cyclopentyl group, a cyclohexyl group, etc.) ), Alkenyl groups (for example, vinyl group, allyl group, etc.), alkynyl groups (for example, ethynyl group, propargyl group,
  • At least one of R3 and R4 is a halogen atom, a cyano group, or an optionally substituted alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group) , Dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc., or those in which hydrogen atoms of these alkyl groups are substituted, cycloalkyl groups (for example, cyclopentyl group, cyclohexyl group, etc.), alkenyl groups (for example, vinyl) Group, allyl group, etc.), alkynyl group (eg, ethynyl group, propargyl group, etc.), alkoxy group (eg, methoxy group, ethoxy group, propyloxy group, pent
  • Ra, Rb, Rc and Rd are each independently a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl group (eg, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group).
  • an optionally substituted alkyl group eg, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group.
  • cycloalkyl group for example, cyclopentyl group, cyclohexyl group, etc.
  • An alkenyl group for example, vinyl group, allyl group, etc.
  • an alkynyl group for example, ethynyl group, propargyl group, etc.
  • an alkoxy group for example, methoxy group, ethoxy group, propyloxy group, pentyloxy group, hexyloxy group, Octyloxy group, dodecyloxy group, etc.
  • cycloalkyloxy group For example, cyclopentyloxy group, cyclohexyloxy group, etc.), amino group (for example, amino group, ethyloxy group, etc.
  • na and nc represent 1 or 2
  • nb and nd represent an integer of 1 to 3.
  • Ra, Rb, Rc and Rd may be the same or different from each other. Arbitrary two of Ra, Rb, Rc and Rd may be bonded to form a cyclic structure.
  • the phosphorescent organometallic complex represented by the general formula (2) according to the present invention will be described.
  • the phosphorescent organometallic complex having the compound represented by the general formula (1) as a ligand of the present invention is a compound represented by the general formula (2).
  • Ring A, ring B and ring C represent a 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocycle, and Z represents CH or N.
  • Cy represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocycle, non-aromatic hydrocarbon ring or non-aromatic heterocycle
  • R1 and R2 each independently represent a hydrogen atom, a halogen atom, or a cyano group Or an optionally substituted alkyl group, cycloalkyl group, alkenyl group, alkynyl group, alkoxy group, cycloalkyloxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl group, aryloxy group, It represents a heteroaryloxy group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group.
  • Ra, Rb and Rc are each independently a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl group, cycloalkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl.
  • R is a halogen atom, a cyano group, an optionally substituted alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, a heteroaryl group, an aryloxy group Represents a heteroaryloxy group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and n0 represents an integer of 1 to 5.
  • Ra, Rb, Rc and R may be the same or different from each other.
  • L is one or more of monoanionic bidentate ligands coordinated to M.
  • monoanionic bidentate ligands are shown below, but the present invention is not limited thereto.
  • M represents a transition metal atom having an atomic number of 40 or more and a group 8 to 10 in the periodic table.
  • Specific metal atoms include Ru, Rh, Pd, Os, Ir, and Pt.
  • M represents 2 or 3, and n represents an integer of 1 to 3. However, m ⁇ n.
  • Ring A, ring B and ring C represent a 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocycle, and Z represents CH or N.
  • Cy represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocycle, non-aromatic hydrocarbon ring or non-aromatic heterocycle.
  • R1, R2, R3 and R4 are each independently a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a cycloalkyloxy group, an amino group ,
  • R3 and R4 may be the same or different.
  • Ra, Rb, Rc and Rd are each independently a hydrogen atom, halogen atom, cyano group, optionally substituted alkyl group, cycloalkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, aryl
  • An alkyl group, an aryl group, a heteroaryl group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group is represented, na and nc represent 1 or 2, and nb and nd represent an integer of 1 to 3.
  • Ra, Rb, Rc and Rd may be the same as or different from each other.
  • L is one or more of monoanionic bidentate ligands coordinated to M.
  • M represents a transition metal atom having an atomic number of 40 or more and a group 8 to 10 in the periodic table.
  • m represents 2 or 3
  • n represents an integer of 1 to 3. However, m ⁇ n.
  • Ring A, ring B, ring C, R1, R2, R3, R4, Ra, Rb, Rc, Rd, L, M, m, n, and Cy are described in detail in formulas (1) and (1-1). , (2) in the description.
  • Ring A and Ring C represent a 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocycle
  • Cy represents a 5- or 6-membered aromatic hydrocarbon ring, aromatic heterocycle, or non-aromatic hydrocarbon
  • R1, R2, R3 and R4 are each independently a hydrogen atom, a halogen atom, a cyano group, an optionally substituted alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a cycloalkyloxy group, an amino group ,
  • R3 and R4 may be the same or different.
  • Ra, Rb, Rc and Rd are each independently a hydrogen atom, halogen atom, cyano group, optionally substituted alkyl group, cycloalkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, aryl Represents an alkyl group, an aryl group, a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, na and nc represent 1 or 2, and nb and nd represent an integer of 1 to 3.
  • Ra, Rb, Rc and Rd may be the same as or different from each other.
  • L is one or more of monoanionic bidentate ligands coordinated to M.
  • M represents a transition metal atom having an atomic number of 40 or more and a group 8 to 10 in the periodic table.
  • m represents 2 or 3
  • n represents an integer of 1 to 3. However, m ⁇ n.
  • a 500 ml four-headed flask was charged with 60 g (234 mmol) of 4-bromo-2,6-diisopropylaniline, 61 g (500 mmol) of phenylboronic acid, 200 ml of toluene, and 50 ml of ethanol, and a condenser tube was attached.
  • 110 g (800 mmol) of potassium carbonate was added, and nitrogen gas was blown in for about 1 hour to substitute with nitrogen.
  • 10.4 g (9 mmol) of tetrakistriphenylphosphine palladium (0) complex was added, and the reaction was carried out under heating and reflux for 10 hours.
  • reaction solution was cooled to room temperature, insolubles were removed by filtration, washed with brine to neutrality, and concentrated under reduced pressure.
  • Fluorescent dopant also called fluorescent compound
  • Fluorescent dopants include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes , Polythiophene dyes, or rare earth complex phosphors.
  • Injection layer electron injection layer, hole injection layer >> The injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, it exists between the anode and the light emitting layer or the hole transport layer and between the cathode and the light emitting layer or the electron transport layer. May be.
  • An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance.
  • Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • anode buffer layer (hole injection layer) The details of the anode buffer layer (hole injection layer) are described in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069 and the like.
  • copper phthalocyanine is used.
  • Representative phthalocyanine buffer layer oxide buffer layer typified by vanadium oxide, amorphous carbon buffer layer, polymer buffer layer using conductive polymer such as polyaniline (emeraldine) or polythiophene, tris (2-phenylpyridine) )
  • Orthometalated complex layers represented by iridium complexes and the like.
  • azatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as the hole injection material.
  • cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc.
  • Metal buffer layer typified by lithium, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide, etc.
  • the buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m, although it depends on the material.
  • ⁇ Blocking layer hole blocking layer, electron blocking layer>
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on November 30, 1998)” on page 237. There is a hole blocking (hole blocking) layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the structure of the electron transport layer described later can be used as a hole blocking layer according to the present invention, if necessary.
  • the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
  • the hole blocking layer contains the carbazole derivative, carboline derivative, or diazacarbazole derivative (shown in which any one of the carbon atoms constituting the carboline ring of the carboline derivative is replaced by a nitrogen atom). It is preferable to contain.
  • the organic EL element when the organic EL element has a plurality of light emitting layers having different emission colors, it is preferable that the light emitting layer whose emission maximum wavelength is the shortest is the closest to the anode among all the light emitting layers. In such a case, it is preferable to additionally provide a hole blocking layer between the shortest wave layer and the light emitting layer next to the anode next to the layer. Furthermore, it is preferable that 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.
  • the ionization potential is defined by the energy required to emit electrons at the HOMO (highest occupied molecular orbital) level of the compound to the vacuum level, and can be obtained by the following method, for example.
  • Gaussian 98 Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.
  • the ionization potential can be obtained as a value obtained by rounding off the second decimal place of the value (eV unit converted value) calculated by performing structural optimization using B3LYP / 6-31G *. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
  • the ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy.
  • a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd. or a method known as ultraviolet photoelectron spectroscopy can be suitably used.
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved.
  • the structure of the hole transport layer described later can be used as an electron blocking layer as necessary.
  • the film thickness of the hole blocking layer and the electron transport layer according to the present invention is preferably 3 nm to 100 nm, and more preferably 5 nm to 30 nm.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • azatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as the hole transport material.
  • the above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminoph
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
  • cyclometalated complexes and orthometalated complexes such as copper phthalocyanine and tris (2-phenylpyridine) iridium complex can also be used as the hole transport material.
  • JP-A-11-251067 J. Org. Huang et. al.
  • a so-called p-type hole transport material described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used.
  • these materials are preferably used because a light-emitting element with higher efficiency can be obtained.
  • the hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can.
  • the thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the hole transport layer may have a single layer structure composed of one or more of the above materials.
  • a hole transport layer having a high p property doped with impurities examples thereof include JP-A-4-297076, JP-A-2000-196140, and JP-A-2001-102175. Appl. Phys. 95, 5773 (2004), and the like.
  • a hole transport layer having such a high p property because a device with lower power consumption can be produced.
  • the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • the electron transport layer can be provided as a single layer or a plurality of layers.
  • an electron transport material also serving as a hole blocking material used for an electron transport layer adjacent to the light emitting layer on the cathode side is injected from the cathode.
  • Any material may be used as long as it has a function of transferring electrons to the light-emitting layer, and any material known in the art can be selected and used alone or in combination.
  • nitro-substituted fluorene Derivatives diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum, Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc.
  • the central metals of these metal complexes are In, Mg, Cu , Ca, Sn, Ga, or Pb can also be used as an electron transport material.
  • metal-free or metal phthalocyanine or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
  • the distyrylpyrazine derivative exemplified as the material for the light emitting layer can also be used as an electron transport material, and an inorganic semiconductor such as n-type-Si, n-type-SiC, etc. as in the case of the hole injection layer and the hole transport layer. Can also be used as an electron transporting material.
  • the electron transport layer can be formed by thinning the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method.
  • the thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the electron transport layer may have a single layer structure composed of one or more of the above materials.
  • an electron transport layer having a high n property doped with impurities examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. Appl. Phys. 95, 5773 (2004), and the like.
  • an electron transport layer having such a high n property because an element with lower power consumption can be produced.
  • an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not so high (about 100 ⁇ m or more)
  • a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • a wet film forming method such as a printing method or a coating method can be used.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 nm to 1000 nm, preferably 10 nm to 200 nm.
  • cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 nm to 200 nm.
  • the anode or the cathode of the organic EL element is transparent or translucent, the light emission luminance is improved, which is convenient.
  • a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a film thickness of 1 nm to 20 nm. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
  • a support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. May be opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.
  • polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfone , Polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylates, cyclone resins such as Arton (trade name JSR) or Appel (trade name Mits
  • an inorganic film, an organic film or a hybrid film of both may be formed on the surface of the resin film.
  • the water vapor permeability (25 ⁇ 0.5 ° C.) measured by a method according to JIS K 7129-1992. , Relative humidity (90 ⁇ 2)% RH) is preferably 0.01 g / (m 2 ⁇ 24 h) or less, and further, oxygen measured by a method according to JIS K 7126-1987.
  • a high barrier film having a permeability of 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less and a water vapor permeability of 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less is preferable.
  • the material for forming the barrier film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
  • the method for forming the barrier film is not particularly limited.
  • the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, and the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.
  • the opaque support substrate examples include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
  • the external extraction efficiency at room temperature of light emission of the organic EL element of the present invention is preferably 1% or more, more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element ⁇ 100.
  • a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination.
  • the ⁇ max of light emission of the organic EL element is preferably 480 nm or less.
  • ⁇ Sealing> As a sealing means used for this invention, the method of adhere
  • the sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Further, transparency and electrical insulation are not particularly limited.
  • Specific examples include a glass plate, a polymer plate / film, and a metal plate / film.
  • the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
  • the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
  • a polymer film and a metal film can be preferably used because the element can be thinned.
  • the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 ⁇ 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less, and a method according to JIS K 7129-1992. It is preferable that the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) measured in (1) is 1 ⁇ 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less.
  • sealing member For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.
  • the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant may be dispersed in the adhesive.
  • Application of the adhesive to the sealing portion may be performed using a commercially available dispenser or may be printed like screen printing.
  • the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
  • the material for forming the film may be a material having a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
  • vacuum deposition method sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma
  • a polymerization method a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil
  • a vacuum is also possible.
  • a hygroscopic compound can also be enclosed inside.
  • hygroscopic compound examples include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
  • metal oxides for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
  • sulfates for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate.
  • metal halides eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.
  • perchloric acids eg perchloric acid Barium, magnesium perchlorate, and the like
  • anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
  • a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the support substrate with the organic layer interposed therebetween or on the sealing film.
  • the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, and the like used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
  • the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light undergoes total reflection between the light and the light, and the light is guided through the transparent electrode or the light emitting layer.
  • a method of improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate and preventing total reflection at the transparent substrate and the air interface (US Pat. No. 4,774,435), A method for improving efficiency by giving light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on the side surface of an element (Japanese Patent Laid-Open No. 1-220394), light emission from a substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the bodies (Japanese Patent Laid-Open No.
  • these methods can be used in combination with the organic EL device of the present invention.
  • a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • the low refractive index layer examples include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.
  • the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.
  • the method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.
  • This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
  • Light that cannot be emitted due to total internal reflection between layers is diffracted by introducing a diffraction grating in any layer or medium (in a transparent substrate or transparent electrode), and the light is removed. I want to take it out.
  • the diffraction grating to be introduced has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much.
  • the refractive index distribution a two-dimensional distribution
  • the light traveling in all directions is diffracted, and the light extraction efficiency is increased.
  • the position where the diffraction grating is introduced may be in any of the layers or in the medium (in the transparent substrate or the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.
  • the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction grating is preferably two-dimensionally repeated such as a square lattice, a triangular lattice, or a honeycomb lattice.
  • the organic EL device of the present invention is processed on the light extraction side of the substrate so as to provide, for example, a microlens array structure, or combined with a so-called condensing sheet, for example, with respect to a specific direction, for example, the device light emitting surface.
  • a specific direction for example, the device light emitting surface.
  • quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably 10 ⁇ m to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
  • the condensing sheet it is possible to use, for example, a sheet that has been put to practical use in an LED backlight of a liquid crystal display device.
  • a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • BEF brightness enhancement film
  • the shape of the prism sheet for example, the base material may be formed by forming a ⁇ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.
  • a light diffusion plate / film may be used in combination with the light collecting sheet.
  • a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
  • a desired electrode material for example, a thin film made of an anode material is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm.
  • organic compound thin films such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer, which are organic EL element materials, are formed thereon.
  • a method for forming each of these layers there are a vapor deposition method, a wet process (spin coating method, casting method, ink jet method, printing method) and the like as described above.
  • film formation by a coating method such as a spin coating method, an ink jet method, or a printing method is preferable in the present invention.
  • liquid medium for dissolving or dispersing the organic EL material according to the present invention examples include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene.
  • Aromatic hydrocarbons such as cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, and organic solvents such as DMF and DMSO can be used.
  • a dispersion method it can disperse
  • a thin film made of a cathode material is formed thereon by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 50 nm to 200 nm.
  • a desired organic EL element can be obtained.
  • a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode.
  • An alternating voltage may be applied.
  • the alternating current waveform to be applied may be arbitrary.
  • the organic EL element of the present invention can be used as a display device, a display, and various light emission sources.
  • lighting devices home lighting, interior lighting
  • clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light
  • the light source of a sensor etc. are mentioned, It is not limited to this, It can use effectively for the use as a backlight of a liquid crystal display device, and an illumination light source especially.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like during film formation, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned.
  • a conventionally known method is used. Can do.
  • the light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with a total CS-1000 (manufactured by Konica Minolta Sensing) is applied to the CIE chromaticity coordinates.
  • the display device of the present invention comprises the organic EL element of the present invention.
  • the display device of the present invention may be single color or multicolor, the multicolor display device will be described here.
  • 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 vapor deposition, casting, spin coating, ink jet, printing, or the like.
  • the method is not limited.
  • the vapor deposition method, the ink jet method, the spin coating method, and the printing method are preferable.
  • the configuration of the organic EL element included in the display device is selected from the organic EL elements of the present invention as necessary.
  • the manufacturing method of an organic EL element is as having shown in the one aspect
  • the multicolor display device can be used as a display device, a display, and various light emission sources.
  • full-color display is possible by using three types of organic EL elements of red, green, and blue light emission.
  • the display device and display include a television, a personal computer, a mobile device, an AV device, a character broadcast display, and an information display in an automobile.
  • the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.
  • Light emitting sources include household 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 sources for optical sensors, etc.
  • the present invention is not limited to these examples.
  • FIG. 1 is a schematic perspective view showing an example of the configuration of a display device composed of the organic EL element of the present invention, which displays image information by light emission of the organic EL element, for example, a display such as a mobile phone FIG.
  • the display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
  • the control unit B is electrically connected to the display unit A.
  • the control unit B sends a scanning signal and an image data signal to each of the plurality of pixels based on image information from the outside.
  • each pixel sequentially emits light according to the image data signal for each scanning line by the scanning signal, and the image information is displayed on the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A shown in FIG.
  • the display unit A includes a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate.
  • the main members of the display unit A will be described below.
  • FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).
  • Each of the scanning lines 5 and the plurality of data lines 6 in the wiring portion is made of a conductive material.
  • 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 are not shown).
  • the pixel 3 When a scanning signal is transmitted from the scanning line 5, the pixel 3 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 appropriately arranging pixels in the red region, the green region, and the blue region in the same substrate on the same substrate.
  • the lighting device of the present invention will be described.
  • the lighting device of the present invention has the organic EL element of the present invention.
  • the organic EL element of the present invention may be used as an organic EL element having a resonator structure, and the purpose of use of the organic EL element having such a resonator structure is as follows.
  • the light source of a machine, the light source of an optical communication processing machine, the light source of a photosensor, etc. are mentioned, However It is not limited to these. Moreover, you may use for the said use by making a laser oscillation.
  • the organic EL element 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, or a display for directly viewing a still image or a moving image. It may be used as a device (display).
  • the driving method when used as a display device for moving image reproduction may be either a simple matrix (passive matrix) method or an active matrix method.
  • a simple matrix (passive matrix) method or an active matrix method.
  • 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 to obtain white light emission by color mixing.
  • the combination of a plurality of emission colors may include three emission maximum wavelengths of the three primary colors of red, green and blue, or two using the complementary colors such as blue and yellow, blue green and orange.
  • the thing containing the light emission maximum wavelength may be used.
  • a combination of light emitting materials for obtaining a plurality of emission colors is a combination of a plurality of phosphorescent or fluorescent materials, a light emitting material that emits fluorescence or phosphorescence, and light from the light emitting material as excitation light. Any of those combined with a dye material that emits 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.
  • an electrode film or the like can be formed by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, or the like, 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 are luminescent white.
  • a luminescent material used for a light emitting layer For example, if it is a backlight in a liquid crystal display element, the metal complex which concerns on this invention so that it may suit the wavelength range corresponding to CF (color filter) characteristic, Any one of known light emitting materials may be selected and combined to be whitened.
  • CF color filter
  • FIG. 3 and FIG. 3 One aspect of the lighting device of the present invention that includes the organic EL element of the present invention will be described.
  • the non-light emitting surface of the organic EL device of the present invention is covered with a glass case, a glass substrate having a thickness of 300 ⁇ m is used as a sealing substrate, and an epoxy photocurable adhesive (LUX TRACK manufactured by Toagosei Co., Ltd.) is used as a sealing material around LC0629B) is applied, and this is overlaid on the cathode to be in close contact with the transparent support substrate, irradiated with UV light from the glass substrate side, cured and sealed, and as shown in FIG. 3 and FIG. Can be formed.
  • FIG. 3 shows a schematic diagram of the illumination device.
  • the organic EL element 101 is covered with a glass cover 102.
  • the sealing operation with the glass cover 102 is performed in a glove box (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more) in a nitrogen atmosphere without bringing the organic EL element 101 into contact with the atmosphere.
  • FIG. 4 shows a cross-sectional view of the lighting device.
  • the cathode 105 and the organic EL layer 106 are formed on a glass substrate 107 with a transparent electrode.
  • the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of the hole injection material 1 is put into a molybdenum resistance heating boat, and 200 mg of the hole transport material 1 is put into another molybdenum resistance heating boat, 200 mg of OC-6 as a host compound is put into another molybdenum resistance heating boat, 100 mg of Comparative Compound 1 as a dopant compound is put into another molybdenum resistance heating boat, and 200 mg of the electron transport material 1 is put into another molybdenum resistance heating boat. Further, 200 mg of the electron transport material 2 was put in another resistance heating boat made of molybdenum, and attached to a vacuum deposition apparatus.
  • the pressure in the vacuum chamber is reduced to 4 ⁇ 10 ⁇ 4 Pa, and then the heating boat containing the hole injection material 1 is heated and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second.
  • a hole injection layer having a thickness of 20 nm was provided.
  • the heating boat containing the hole transport material 1 is energized and heated, and deposited on the hole injection layer at a deposition rate of 0.1 nm / second. Then, a hole transport layer having a thickness of 20 nm was provided.
  • the hole transport layer was heated by energizing the heating boat containing OC-6 as a host compound and Comparative Compound 1 as a dopant compound, respectively, at a deposition rate of 0.2 nm / second and 0.012 nm / second, respectively.
  • a 40 nm-thick luminescent layer was provided by co-evaporation.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the heating boat containing the electron transport material 1 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a 10 nm thick hole blocking layer.
  • the heating boat containing the electron transporting material 2 is further energized and heated, and deposited on the hole blocking layer at a deposition rate of 0.1 nm / second to provide an electron transporting layer having a thickness of 20 nm. It was.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride 0.5 nm and aluminum 110 nm were vapor-deposited to form a cathode, and an organic EL element 1-1 was produced.
  • Luminescence half-life The luminescence half-life was evaluated according to the measurement method shown below. It is necessary for each organic EL element to be driven at a constant current at room temperature (about 23 to 25 ° C.) and with a current that gives an initial luminance of 2000 cd / m 2 so that the emission luminance becomes 1/2 of the initial luminance (1000 cd / m 2 ). Time (half-life) was determined and used as a measure of the luminescence half-life. The light emission half-life was expressed as a relative value where the half-life of the organic EL device 1-1 was 100.
  • the organic EL elements 1-9 to 1-28 of the present invention have higher external extraction quantum efficiency than the organic EL elements 1-1 to 1-8 of the comparative example, It can be seen that the initial luminance degradation is small and the lifetime is accordingly increased. Further, it can be seen that in the organic EL elements 1-9 to 1-28 of the present invention, the generation of dark spots is also suppressed.
  • the substrate was transferred to a nitrogen atmosphere, and a thin film was formed on the first hole transport layer by spin coating using a solution of 50 mg of hole transport material 3 dissolved in 10 ml of toluene at 1000 rpm for 30 seconds. Formed. Further, ultraviolet light was irradiated for 180 seconds to perform photopolymerization / crosslinking, and then vacuum-dried at 60 ° C. for 1 hour to form a second hole transport layer.
  • a solution obtained by dissolving 100 mg of the host material 1 as a host compound and 15 mg of the comparative compound 1 as a dopant compound in 10 ml of butyl acetate is spinned at 600 rpm for 30 seconds.
  • a thin film was formed by a coating method. Further, ultraviolet light was irradiated for 15 seconds to perform photopolymerization / crosslinking, and then vacuum-dried at 60 ° C. for 1 hour to obtain a light emitting layer having a thickness of about 70 nm.
  • a thin film was formed on this light emitting layer by spin coating under a condition of 1000 rpm and 30 seconds using a solution in which 50 mg of the electron transport material 3 was dissolved in 10 ml of hexafluoroisopropanol (HFIP). Furthermore, it vacuum-dried at 60 degreeC for 1 hour, and was set as the electron carrying layer with a film thickness of about 30 nm.
  • HFIP hexafluoroisopropanol
  • this substrate was fixed to a substrate holder of a vacuum evaporation apparatus, and after the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa, 0.4 nm of potassium fluoride was evaporated to form a cathode buffer layer, and further, aluminum 110 nm.
  • the organic EL element 2-1 was produced by forming a cathode by vapor deposition.
  • the organic EL elements 2-9 to 2-28 of the present invention have a higher external extraction quantum efficiency and an initial luminance deterioration as compared with the organic EL elements 2-1 to 2-8 of the comparative example. It can be seen that is small and has a long life. Furthermore, it can be seen that in the organic EL elements 2-9 to 2-28 of the present invention, the generation of dark spots is also suppressed.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of the hole injection material 1 is put into a molybdenum resistance heating boat, and 200 mg of the hole transport material 1 is put into another molybdenum resistance heating boat, In another molybdenum resistance heating boat, 200 mg of OC-6 as a host compound was placed, and in another molybdenum resistance heating boat, 100 mg of Comparative Compound 1 as the first dopant compound was placed.
  • Ir-9 100 mg was added as a dopant compound, 200 mg of the electron transport material 1 was placed in another molybdenum resistance heating boat, and 200 mg of the electron transport material 2 was placed in another resistance heating boat made of molybdenum, and attached to a vacuum deposition apparatus.
  • the pressure in the vacuum chamber is reduced to 4 ⁇ 10 ⁇ 4 Pa, and then the heating boat containing the hole injection material 1 is heated and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second.
  • a hole injection layer having a thickness of 20 nm was provided.
  • the heating boat containing the hole transport material 1 is energized and heated, and deposited on the hole injection layer at a deposition rate of 0.1 nm / second. Then, a hole transport layer having a thickness of 20 nm was provided.
  • the heating boat containing OC-6 as a host compound, Comparative compound 1 as a first dopant compound and Ir-9 as a second dopant compound was heated by energization, and the deposition rate was 0.2 nm, respectively.
  • a light emitting layer having a thickness of 40 nm was provided by co-evaporation on the hole transport layer at a rate of 0.020 nm / second, 0.020 nm / second, and 0.0010 nm / second.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the heating boat containing the electron transport material 1 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a 10 nm thick hole blocking layer.
  • the heating boat containing the electron transporting material 2 is further energized and heated, and deposited on the hole blocking layer at a deposition rate of 0.1 nm / second to provide an electron transporting layer having a thickness of 20 nm. It was.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride 0.5 nm and aluminum 110 nm were vapor-deposited to form a cathode, and an organic EL element 3-1 was produced.
  • the organic EL elements 3-9 to 3-28 of the present invention have a higher external extraction quantum efficiency than the organic EL elements 3-1 to 3-8 of the comparative example, and the initial luminance degradation. It can be seen that is small and has a long life. Furthermore, it can be seen that in the organic EL elements 3-9 to 3-28 of the present invention, the generation of dark spots is also suppressed.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of the hole injection material 1 is put into a molybdenum resistance heating boat, and 200 mg of the hole transport material 1 is put into another molybdenum resistance heating boat, In another molybdenum resistance heating boat, 200 mg of OC-1 as a host compound was placed, and in another molybdenum resistance heating boat, 100 mg of Comparative Compound 1 as a first dopant compound was placed.
  • the heating boat containing the hole injection material 1 was energized and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / sec.
  • the hole injection layer was provided.
  • the heating boat containing the hole transport material 1 is energized and heated, and deposited on the hole injection layer at a deposition rate of 0.1 nm / second. Then, a hole transport layer having a thickness of 20 nm was provided.
  • the heating boat containing OC-1 as a host compound and comparative compound 1 as a first dopant compound was heated by energization, and the positive rate was increased at a deposition rate of 0.2 nm / second and 0.020 nm / second, respectively.
  • a blue light emitting layer having a thickness of 20 nm was provided by co-evaporation on the hole transport layer.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the heating boat containing OC-1 as the host compound, Ir-9 as the second dopant compound, and Ir-2 as the third dopant compound was heated by energization, and the deposition rate was 0.2 nm, respectively.
  • / Yellow, 0.0010 nm / second, and 0.010 nm / second were co-evaporated on the blue light emitting layer to provide a yellow light emitting layer having a thickness of 20 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the heating boat containing the electron transport material 1 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a 10 nm thick hole blocking layer.
  • the heating boat containing the electron transport material 2 is further energized and heated, and deposited on the hole blocking layer at a deposition rate of 0.1 nm / second to form an electron transport layer having a thickness of 20 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride 0.5 nm and aluminum 110 nm were vapor-deposited to form a cathode, and an organic EL element 3-1 was produced.
  • the organic EL elements 4-9 to 4-28 of the present invention have higher external extraction quantum efficiency and initial luminance degradation as compared with the organic EL elements 4-1 to 4-8 of the comparative examples. It can be seen that is small and has a long life. Furthermore, it can be seen that in the organic EL elements 4-9 to 4-28 of the present invention, the formation of dark spots is also suppressed.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of the hole injection material 1 is put into a molybdenum resistance heating boat, and 200 mg of the hole transport material 1 is put into another molybdenum resistance heating boat, Another molybdenum resistance heating boat is charged with 200 mg of OC-1 as the first host compound, and another molybdenum resistance heating boat is charged with 200 mg of OC-6 as the second host compound 2, and another molybdenum resistance heating boat.
  • Comparative Compound 1 as a first dopant compound, 100 mg of Ir-9 as a second dopant compound in another molybdenum resistance heating boat, and Ir as a third dopant compound in another molybdenum resistance heating boat -2 is put in 100mg, and the electron transport material 1 is put on another molybdenum resistance heating boat. It placed 200 mg, further an electron transporting material 2 placed 200mg in a third resistive heating molybdenum boat, mounted in a vacuum deposition apparatus.
  • the pressure in the vacuum chamber is reduced to 4 ⁇ 10 ⁇ 4 Pa, and then the heating boat containing the hole injection material 1 is heated and heated, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second.
  • a hole injection layer having a thickness of 20 nm was provided.
  • the heating boat containing the hole transport material 1 is energized and heated, and deposited on the hole injection layer at a deposition rate of 0.1 nm / second. Then, a hole transport layer having a thickness of 20 nm was provided.
  • the heating boat containing OC-1 as a host compound and comparative compound 1 as a first dopant compound was heated by energization, and the positive rate was increased at a deposition rate of 0.2 nm / second and 0.020 nm / second, respectively.
  • a blue light emitting layer having a thickness of 20 nm was provided by co-evaporation on the hole transport layer.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the heating boat containing OC-6) as the host compound, Ir-9 as the second dopant compound, and Ir-2 as the third dopant compound was heated while being energized.
  • a 20 nm-thick yellow light emitting layer was provided by co-evaporation on the blue light emitting layer at 2 nm / second, 0.0010 nm / second, and 0.010 nm / second.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the heating boat containing the electron transport material 1 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a 10 nm thick hole blocking layer.
  • the heating boat containing the electron transporting material 2 is further energized and heated, and deposited on the hole blocking layer at a deposition rate of 0.1 nm / second to provide an electron transporting layer having a thickness of 20 nm. It was.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride 0.5 nm and aluminum 110 nm were vapor-deposited to form a cathode, and an organic EL element 3-1 was produced.
  • the organic EL elements 5-9 to 5-28 of the present invention have higher external extraction quantum efficiency and initial luminance degradation than the organic EL elements 5-1 to 5-8 of the comparative examples. It can be seen that is small and has a long life. Further, it can be seen that in the organic EL elements 5-9 to 5-28 of the present invention, the generation of dark spots is suppressed.
  • Preparation of white light-emitting organic EL element 6-1 After patterning on a substrate (NA-45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) as an anode on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm, this ITO transparent electrode is provided.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • the substrate was transferred to a nitrogen atmosphere, and a thin film was formed on the first hole transport layer by spin coating using a solution of 50 mg of hole transport material 3 dissolved in 10 ml of toluene at 1000 rpm for 30 seconds. Formed. Further, ultraviolet light was irradiated for 180 seconds to perform photopolymerization / crosslinking, and then vacuum-dried at 60 ° C. for 1 hour to form a second hole transport layer.
  • a thin film was formed on this light emitting layer by spin coating under a condition of 1000 rpm and 30 seconds using a solution in which 50 mg of the electron transport material 3 was dissolved in 10 ml of hexafluoroisopropanol (HFIP). Furthermore, it vacuum-dried at 60 degreeC for 1 hour, and was set as the electron carrying layer with a film thickness of about 30 nm.
  • HFIP hexafluoroisopropanol
  • this substrate was fixed to a substrate holder of a vacuum evaporation apparatus, and after the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa, 0.4 nm of potassium fluoride was evaporated to form a cathode buffer layer, and further, aluminum 110 nm.
  • the organic EL element 6-1 was produced by forming a cathode by vapor deposition.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the organic EL elements 6-9 to 6-28 of the present invention have higher external extraction quantum efficiency and initial luminance degradation than the organic EL elements 6-1 to 6-8 of the comparative example. It can be seen that is small and has a long life. Furthermore, it can be seen that in the organic EL elements 6-9 to 6-28 of the present invention, the formation of dark spots is also suppressed.
  • the substrate was transferred to a nitrogen atmosphere, and a thin film was formed on the first hole transport layer by spin coating using a solution of 50 mg of hole transport material 3 dissolved in 10 ml of toluene at 1000 rpm for 30 seconds. Formed. Further, ultraviolet light was irradiated for 180 seconds to perform photopolymerization / crosslinking, and then vacuum-dried at 60 ° C. for 1 hour to form a second hole transport layer.
  • a second hole transport layer 100 mg of host material 1 as a host compound, 10 mg of comparative compound 1 as a first dopant compound, 1 mg of Ir-2 as a second dopant compound, and a third dopant Using a solution of 0.5 mg Ir-21 as a compound dissolved in 10 ml butyl acetate, a thin film was formed by spin coating under conditions of 1000 rpm and 30 seconds. Further, ultraviolet light was irradiated for 15 seconds to perform photopolymerization / crosslinking, and then vacuum-dried at 60 ° C. for 1 hour to obtain a light emitting layer having a thickness of about 70 nm.
  • a thin film was formed on the light emitting layer by spin coating under a condition of 1000 rpm for 30 seconds using a solution of 50 mg of the electron transport material 4 dissolved in 10 ml of methanol. Further, ultraviolet light was irradiated for 60 seconds to perform photopolymerization / crosslinking, and then vacuum-dried at 60 ° C. for 1 hour to obtain an electron transport layer having a film thickness of about 30 nm.
  • this substrate was fixed to a substrate holder of a vacuum evaporation apparatus, and after the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa, 0.4 nm of potassium fluoride was evaporated to form a cathode buffer layer, and further, aluminum 110 nm.
  • the organic EL element 7-1 was produced by forming a cathode by vapor deposition.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • the organic EL elements 7-9 to 7-28 of the present invention have higher external extraction quantum efficiency and initial luminance degradation as compared with the organic EL elements 7-1 to 7-8 of the comparative example. It can be seen that is small and has a long life. Furthermore, it can be seen that in the organic EL elements 7-9 to 7-28 of the present invention, the formation of dark spots is also suppressed.
  • the present invention provides an organic EL element, an illuminating device, and a display device using an organic EL element material that exhibits high light emission efficiency in a high luminance light emission region (over 2000 cd / m 2 ) and has a long light emission lifetime. Suitable for doing. Furthermore, the present invention provides an organic EL element material that exhibits high luminous efficiency, has a low driving voltage, and has a long emission lifetime in white light emission, and a wet process with high productivity of such an organic EL element material. Suitable for providing in.

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

Abstract

La présente invention concerne un élément électroluminescent organique, dans lequel au moins une couche organique contenant une couche électroluminescente est intercalée entre une électrode positive et une électrode négative. Au moins une des couches organiques contient un complexe métallique organique électroluminescent phosphorescent, dans lequel un ligand représenté par la formule générale (1) est coordonné sur un atome métallique.
PCT/JP2012/071762 2011-09-02 2012-08-29 Élément électroluminescent organique, dispositif d'affichage, et dispositif d'éclairage WO2013031794A1 (fr)

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JP2015174824A (ja) * 2014-03-13 2015-10-05 住友化学株式会社 金属錯体およびそれを用いた発光素子
JP2017108135A (ja) * 2015-12-07 2017-06-15 住友化学株式会社 発光素子及び金属錯体
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EP3266789A1 (fr) 2013-07-02 2018-01-10 UDC Ireland Limited Complexes métalliques contenant des ligands diazabenzimidazole-carbéniques monosubstitués destinés à être utilisés dans des diodes électroluminescentes organiques
WO2015000955A1 (fr) 2013-07-02 2015-01-08 Basf Se Complexes de métal et de carbène de type diazabenzimidazole monosubstitué destinés à être utilisés dans des diodes électroluminescentes organiques
JP2015174824A (ja) * 2014-03-13 2015-10-05 住友化学株式会社 金属錯体およびそれを用いた発光素子
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US9862739B2 (en) 2014-03-31 2018-01-09 Udc Ireland Limited Metal complexes, comprising carbene ligands having an O-substituted non-cyclometalated aryl group and their use in organic light emitting diodes
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JP2017108135A (ja) * 2015-12-07 2017-06-15 住友化学株式会社 発光素子及び金属錯体
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US20180062084A1 (en) * 2016-08-29 2018-03-01 Semiconductor Energy Laboratory Co., Ltd. Light-Emitting Element, Light-Emitting Device, Electronic Device, Lighting Device, and Organometallic Complex
WO2019065388A1 (fr) * 2017-09-29 2019-04-04 住友化学株式会社 Composition et dispositif électroluminescent utilisant celui-ci
JPWO2019065388A1 (ja) * 2017-09-29 2020-11-05 住友化学株式会社 組成物及びそれを用いた発光素子
JPWO2019065389A1 (ja) * 2017-09-29 2020-11-26 住友化学株式会社 発光素子
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WO2020211128A1 (fr) * 2019-04-16 2020-10-22 武汉华星光电半导体显示技术有限公司 Matériau à fluorescence retardée activé thermiquement, procédé de préparation correspondant et dispositif à diode électroluminescente organique
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