WO2013168534A1 - Élément à électroluminescence organique, procédé de production d'un élément à électroluminescence organique, dispositif d'affichage et dispositif d'éclairage - Google Patents

Élément à électroluminescence organique, procédé de production d'un élément à électroluminescence organique, dispositif d'affichage et dispositif d'éclairage Download PDF

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WO2013168534A1
WO2013168534A1 PCT/JP2013/061538 JP2013061538W WO2013168534A1 WO 2013168534 A1 WO2013168534 A1 WO 2013168534A1 JP 2013061538 W JP2013061538 W JP 2013061538W WO 2013168534 A1 WO2013168534 A1 WO 2013168534A1
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ring
general formula
aromatic
organic electroluminescence
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和博 及川
岩崎　利彦
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コニカミノルタ株式会社
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Definitions

  • the present invention relates to an organic electroluminescence element, a method for manufacturing an organic electroluminescence element, a display device, and a lighting device.
  • an electroluminescence display is known as a light-emitting electronic display device.
  • Examples of the constituent elements of ELD include inorganic electroluminescence elements (inorganic EL elements) and organic electroluminescence elements (organic EL elements).
  • Inorganic EL elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements.
  • an organic EL element has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and excitons (exciton) are injected by injecting electrons and holes into the light emitting layer and recombining them. ) And emits light by utilizing light emission (fluorescence / phosphorescence) when the exciton is deactivated.
  • Organic EL elements can emit light at a voltage of several volts to several tens of volts, and are self-luminous, so they have a wide viewing angle, high visibility, and are thin-film completely solid elements. In particular, it is attracting attention from the viewpoints of space saving and portability. Furthermore, the organic EL element has a feature that it is a surface light source.
  • ⁇ Applications that can make effective use of this characteristic include illumination light sources and various display backlights.
  • illumination light sources and various display backlights.
  • it has become suitable to be used as a backlight for liquid crystal full-color displays where the demand has increased significantly.
  • an organic EL element When an organic EL element is used as such a light source for illumination or a backlight of a display, it is used as a light source whose emission color is white or a so-called light bulb color (hereinafter collectively referred to as white).
  • a method of stacking layers (for example, refer to Patent Document 1), a method of obtaining multicolored light emitting pixels, for example, blue, green, and red, separately, emitting light at the same time, and mixing them to obtain white, color conversion
  • a method of obtaining white using a dye for example, a combination of a blue light emitting dopant and a color conversion fluorescent dye
  • a method of preparing a plurality of light emitting dopants having different emission wavelengths in one element and obtaining white by color mixing, etc.
  • White light emission can be achieved by these methods.
  • the light emitting layers having different light emission colors are laminated, there is a problem that the light emission color is changed because the light emission position is shifted due to the fluctuation of the drive current amount or the change with time during continuous driving.
  • the method using different colors of light-emitting pixels has a problem that the manufacturing process such as mask alignment is complicated and the yield is low, and the color conversion method has a problem that the light emission efficiency is low.
  • Patent Document 2 discloses a method for improving efficiency by using energy transfer between light-emitting dopants coexisting in the same layer.
  • Patent Document 2 even when light emitting dopants having different light emission colors are mixed, only one light emitting dopant emits light, which is not suitable for obtaining white light emission. That is, in order to obtain preferable white light emission with a single light emitting layer, white light emission cannot be obtained with the same ratio of light emitting dopant as in the multilayer structure, and the light emission energy is higher than the light emission dopant with a high light emission energy level.
  • wet processes spin coating method, casting method, ink jet method, spray method, printing method, etc.
  • the wet process is a manufacturing method that has attracted attention in recent years because it does not require a vacuum process and is convenient for continuous production.
  • it is possible to form a light-emitting layer having a desired composition by adjusting the material mixing ratio at the time of preparing the coating liquid, and this is advantageous even in the case of forming a light-emitting layer having a composition with a greatly different mixing ratio. is there.
  • Patent Document 3 by using two types of host materials for one type of phosphorescent light emitting dopant, both the emission inhibition mitigation by energy transfer and the reduction of the injection barrier from the adjacent layer are achieved, and high efficiency and high color purity are achieved. In addition, a long-life organic EL element is achieved.
  • the main object of the present invention is to provide an organic EL device that suppresses aggregation and crystallization of luminescent dopants and is excellent in driving voltage, luminescent efficiency, luminescent lifetime, and solubility. It is to provide a display device, a lighting device, and a method for manufacturing an organic EL element.
  • Another object of the present invention is to suppress aggregation and crystallization of light emitting dopants even when a white light emitting layer containing a plurality of light emitting dopants of different emission colors is formed by a wet process.
  • An organic EL device having excellent luminous efficiency, luminous lifetime and solubility is provided.
  • an organic electroluminescence device in which at least one organic compound layer including a light emitting layer is disposed between an anode and a cathode, At least one of the organic compound layers is formed by a wet process and includes an iridium complex represented by the general formula (1) and a host compound represented by the general formula (A).
  • An organic electroluminescence device is provided.
  • Ring Am”, “Ring An”, “Ring Bm” and “Ring Bn” represent a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocyclic ring.
  • Ar represents an aromatic hydrocarbon ring, an aromatic heterocyclic ring, a non-aromatic hydrocarbon ring or a non-aromatic heterocyclic ring.
  • R1m”, “R2m”, “R1n” and “R2n” are each independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or It represents a non-aromatic heterocyclic group and may further have a substituent.
  • Ra”, “Rb” and “Rc” are each independently a hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group Represents a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent, and “Ra” may form a ring with “Ar”.
  • na represents an integer of 1 to 3
  • nb represents an integer of 1 to 4
  • nc represents 1 or 2.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n is 3. Note that the structures of the three ligands coordinated to Ir are not all the same.
  • X represents NR ′, O, S, CR′R ′′ or SiR′R ′′.
  • R ′ and R ′′ each independently represents a hydrogen atom or a substituent.
  • Ar represents an aromatic ring.
  • n represents an integer of 0 to 8.
  • the organic EL element which suppressed aggregation and crystallization of light emission dopants, was excellent in drive voltage, luminous efficiency, light emission lifetime, and solubility can be provided, and the display apparatus provided with this together And a manufacturing method of an illuminating device and an organic EL element can be provided.
  • the conventional tris body all three bidentate ligands have the same structure
  • iridium complex dopant has at least six dopant-dopant interaction sites, so the probability of the same molecular interaction is high.
  • the iridium complex dopant according to the present invention is asymmetric, two or four interaction sites between the dopants are specified, and it is difficult to form a cluster in which a large number of the same molecules are connected. As a result, the solubility becomes high and does not precipitate, so that the coating solution can be stored for a long time, and the production efficiency is improved, leading to cost reduction.
  • the conventional tris iridium complex in the combination of the conventional tris iridium complex and the host compound, there are six dopant-dopant interaction sites as described above, and the probability of the same molecule interaction is high.
  • the site for stabilizing the interaction energy can be limited to two or four, and the dopant can be prevented from aggregating in a chain.
  • the dopant can be dispersed with fewer host molecules, and as a result, the dopant can be doped at a high concentration.
  • the dopant-host interaction will be stronger than when a conventional tris body is used. It is estimated that the stagnation of the trapped solvent can be suppressed.
  • a host compound represented by the general formula (A) is preferably used as the host compound, and more preferably an asymmetric host compound having a dibenzofuran skeleton is used.
  • the combination of the iridium complex of the present invention and the host compound can also reduce the performance deterioration due to the solvent remaining in the film, which is a problem of the coating film.
  • ⁇ is used to mean that the numerical values described before and after it are included as a lower limit value and an upper limit value.
  • the organic EL element 100 is configured by sequentially laminating an anode 2, an organic compound layer stack 20, and a cathode 8 on a support substrate 1.
  • the laminate 20 is composed of layers containing an organic compound, and includes a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and an electron injection layer 7.
  • an organic compound layer such as a hole blocking layer or an electron blocking layer may be provided.
  • the anode 2, the laminate 20, and the cathode 8 are sealed with a sealing member 10 through a sealing adhesive 9.
  • these layer structures (refer FIG. 1) of the organic EL element 100 show the preferable specific example, and this invention is not limited to these.
  • the organic EL element 100 may have the following layer structures (i) to (ii).
  • the light emission maximum wavelength of the blue light-emitting dopant is preferably in the range of 430 to 480 nm
  • the light emission maximum wavelength of the green light-emitting dopant is in the range of 510 to 550 nm
  • the light emission maximum of the red light-emitting dopant is preferably in the range of 600 to 640 nm, and a display device using these is preferable.
  • the light emitting layer of at least three colors may be laminated to form a white light emitting layer, or a plurality of light emitting colors may be mixed in the same layer. Further, a non-light emitting intermediate layer may be provided between the light emitting layers.
  • the organic EL element 100 of the present invention is preferably a white light emitting layer, and is preferably a lighting device using these.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is within the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.
  • the total film thickness of the light emitting layer is not particularly limited, but from the viewpoint of improving the uniformity of the film, preventing unnecessary application of high voltage during light emission, and improving the stability of the emission color with respect to the drive current. It is preferable to adjust in the range of 2 nm to 5 ⁇ m, more preferably in the range of 2 to 200 nm, and particularly preferably in the range of 10 to 100 nm.
  • the light emitting layer of the organic EL device of the present invention contains a light emitting dopant (such as a phosphorescent light emitting dopant or a fluorescent light emitting dopant) and a host compound.
  • a light emitting dopant such as a phosphorescent light emitting dopant or a fluorescent light emitting dopant
  • Luminescent dopant examples include a fluorescent luminescent dopant and a phosphorescent luminescent dopant (also referred to as a phosphorescent compound, a phosphorescent luminescent compound, etc.).
  • a phosphorescent dopant that is easily affected is preferable from the viewpoint of suppressing molecular aggregation, and specifically, an iridium complex represented by the following general formula (1) that is at least a blue phosphorescent dopant is used. .
  • a phosphorescent light emitting dopant As the light emitting dopant, a phosphorescent light emitting dopant (also referred to as a phosphorescent compound) is preferable because high luminous efficiency is obtained.
  • the phosphorescent dopant is a compound in which light emission from an excited triplet is observed, and is preferably a compound having a phosphorescent quantum yield of 0.01 or more at 25 ° C. More preferably, it is 0.1 or more. In the present invention, any other compound contained in the light emitting layer is used as the host compound.
  • the ratio of the host compound to the phosphorescent light emitting dopant in the light emitting layer is any ratio between 1 and 99% by mass for each compound, assuming that the mass of the compound contained in the entire light emitting layer is 100%. However, it is preferable that the proportion of the host compound is larger than the proportion of the phosphorescent dopant, and more preferably the proportion of the phosphorescent dopant is 1 to 30% by mass.
  • the phosphorescent quantum yield can be measured by the method described in Spectrophoto II, page 398 (1992 edition, Maruzen) of the 4th edition Experimental Chemistry Course 7. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence emission dopant used in the present invention is a compound that achieves the phosphorescence quantum yield in any solvent. .
  • the maximum emission wavelength of the luminescent dopant is the wavelength at which the emission intensity is maximum at the maximum value of the emission spectrum.
  • the emission spectrum of the luminescent dopant is measured as follows. First, the absorption spectrum of the luminescent dopant is measured, and the maximum absorption wavelength in the range of 300 to 350 nm is set as the excitation light. Using the set excitation light, an emission spectrum is measured with a fluorometer F-4500 (manufactured by Hitachi, Ltd.) while performing nitrogen bubbling.
  • the solvent that can be used is not limited, but 2-methyltetrahydrofuran, dichloromethane and the like are preferably used from the viewpoint of solubility of the compound.
  • the concentration at the time of measurement is preferably sufficiently diluted, and specifically, it is preferably measured in the range of 10 ⁇ 6 to 10 ⁇ 4 mol / L.
  • the temperature at the time of measurement is not particularly limited, but it is generally preferable to set the temperature in the range of room temperature to 77K.
  • phosphorescent dopants There are two types of light emission principles of phosphorescent dopants. One is the recombination of carriers on the host compound to which carriers are transported, generating an excited state of the host compound, and this energy is used as the phosphorescent dopant.
  • the energy transfer type of obtaining light emission from the phosphorescent dopant by moving it, 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
  • the excited state energy of the phosphorescent light emitting dopant is required to be lower than the excited state energy of the host compound.
  • the phosphorescent dopant according to the present invention includes at least one blue phosphorescent material, and more specifically includes an iridium complex represented by the following general formula (1).
  • the organic EL element in addition to at least one blue phosphorescent material, at least two phosphorescent materials having a band gap energy lower than that of the blue phosphorescent material are used.
  • the phosphorescent dopant having a lower band gap energy than that of the blue phosphorescent material it can be appropriately selected from conventionally known phosphorescent dopants used in the light emitting layer of the organic EL element, and preferably a periodic table of elements.
  • a complex compound containing a group 8-10 metal more preferably an iridium compound, an osmium compound, a platinum compound (platinum complex compound), or a rare earth complex, and most preferably an iridium compound.
  • Ring Am”, “Ring An”, “Ring Bm” and “Ring Bn” represent a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle
  • Ar represents An aromatic hydrocarbon ring, an aromatic heterocycle, a non-aromatic hydrocarbon ring or a non-aromatic heterocycle
  • R1m”, “R2m”, “R1n” and “R2n” are each independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group, and may further have a substituent.
  • Ra”, “Rb” and “Rc” are each independently a hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, hetero It represents an aryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, may further have a substituent, and “Ra” may form a ring with “Ar”.
  • na represents an integer of 1 to 3
  • nb represents an integer of 1 to 4
  • nc represents 1 or 2.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n is 3. Note that the structures of the three ligands coordinated to Ir are not all the same.
  • examples of the 5-membered or 6-membered aromatic hydrocarbon ring represented by “ring An”, “ring Am”, “ring Bn” and “ring Bm” include a benzene ring. It is done.
  • examples of the 5-membered or 6-membered aromatic heterocycle represented by “ring An”, “ring Am”, “ring Bn” and “ring Bm” include a furan ring and a thiophene ring.
  • at least one of “ring Bn” and “ring Bm” is a benzene ring, more preferably at least one of “ring An” and “ring Am” is a benzene ring.
  • examples of the aromatic hydrocarbon ring represented by “Ar” include a benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene ring, and naphthacene ring.
  • Triphenylene ring Triphenylene ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring , Pyrene ring, pyranthrene ring, anthraanthrene ring and the like.
  • examples of the aromatic heterocycle represented by “Ar” include a silole ring, furan ring, thiophene ring, oxazole ring, pyrrole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, Triazine ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzthiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, thienothiophene ring, carbazole ring , Azacarbazole ring (representing any one or more of the carbon atoms constituting the carbazole ring replaced by a nitrogen atom), dibenzosilole ring, dibenzofuran
  • examples of the non-aromatic hydrocarbon ring represented by “Ar” include cycloalkane (eg, cyclopentane ring, cyclohexane ring, etc.), cycloalkoxy group (eg, cyclopentyloxy group, cyclohexyl). Oxy group, etc.), cycloalkylthio group (for example, cyclopentylthio group, cyclohexylthio group, etc.), cyclohexylaminosulfonyl group, tetrahydronaphthalene ring, 9,10-dihydroanthracene ring, biphenylene ring and the like.
  • examples of the non-aromatic heterocycle represented by “Ar” include an epoxy ring, an aziridine ring, a thiirane ring, an oxetane ring, an azetidine ring, a thietane ring, a tetrahydrofuran ring, a dioxolane ring, and a pyrrolidine ring.
  • these rings represented by “Ar” may have a substituent, and the substituents may be bonded to each other to form a ring.
  • “Ar” is preferably an aromatic hydrocarbon ring or an aromatic heterocyclic ring, more preferably an aromatic hydrocarbon ring, and still more preferably a benzene ring.
  • examples of the alkyl group represented by “R1m” and “R2m” include, for example, methyl group, ethyl group, trifluoromethyl group, isopropyl group, n-butyl group, t-butyl group, n -Hexyl group, 2-methylhexyl group, pentyl group, adamantyl group, n-decyl group, n-dodecyl group and the like.
  • substituent that the heterocyclic group may further have include, for example, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, an arylalkyl group, an aryl group, and a hetero group.
  • both “R1m” and “R2m” are an alkyl group or a cycloalkyl group having 2 or more carbon atoms, and any one of “R1m” and “R2m” is carbon.
  • a branched alkyl group having 3 or more atoms is also preferred. More preferably, both “R1m” and “R2m” are branched alkyl groups having 3 or more carbon atoms.
  • R1n and R2n have the same meanings as “R1m” and “R2m” in the above general formula (1).
  • the aryl group and heteroaryl group represented by “Ra”, “Rb” and “Rc” are aromatic hydrocarbons represented by “Ar” in the above general formula (1). And monovalent groups derived from a ring and an aromatic heterocycle.
  • na represents an integer of 1 to 3, but na in the left ligand as viewed from the front represents 1 or 2, and na in the right ligand as viewed from the front represents 1 to 2.
  • An integer of 3 is represented.
  • the iridium complex represented by the general formula (1) is preferably represented by the following general formula (2).
  • “Ar” represents an aromatic hydrocarbon ring, an aromatic heterocyclic ring, a non-aromatic hydrocarbon ring or a non-aromatic heterocyclic ring.
  • “R1m”, “R2m”, “R1n” and “R2n” are each independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group, and may further have a substituent.
  • Ra and “Rc” are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl 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, a non-group It represents an aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, may further have a substituent, and “Ra” may form a ring with “Ar”.
  • na represents an integer of 1 to 3
  • nc represents 1 or 2.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n is 3. Note that the structures of the three ligands coordinated to Ir are not all the same.
  • the iridium complexes represented by the general formulas (1) and (2) according to the present invention can be synthesized by referring to known methods described in International Publication No. 2006/121811, etc.
  • the iridium complex represented by the general formula (2) is preferably represented by the following general formula (3).
  • R1m”, “R2m”, “R1n” and “R2n” are each independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group or a non-aromatic group. It represents a hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • Ra”, “Rc” and “Ra 3 ” are each independently a hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, It represents a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • na represents an integer of 1 to 3
  • nc represents 1 or 2
  • nR3 represents an integer of 1 to 5.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n is 3. Note that the structures of the three ligands coordinated to Ir are not all the same.
  • R1m”, “R2m”, “R1n”, “R2n”, “Ra”, “Rc”, na, nc, m and n are “R1m” in the general formula (1), It is synonymous with “R2m”, “R1n”, “R2n”, “Ra”, “Rc”, na, nc, m and n.
  • Ra 3 has the same meaning as “Ra”, “Rb”, and “Rc” in the general formula (1).
  • the iridium complex represented by the general formula (1) is preferably represented by the following general formula (4).
  • R1m”, “R2m”, “R1n” and “R2n” are each independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group or a non-aromatic group. It represents a hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • Ra”, “Rc” and “Ra 3 ” are each independently a hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, It represents a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • na represents an integer of 1 to 3
  • nc represents 1 or 2
  • nR3 represents an integer of 1 to 4.
  • X represents O, S, SiRz1Rz2, NRz1 or CRz1Rz2, wherein Rz1 and Rz2 are alkyl groups, aromatic hydrocarbon ring groups, aromatic heterocyclic groups, non-aromatic hydrocarbon ring groups or non-aromatic heterocyclic groups.
  • Rz1 and Rz2 are alkyl groups, aromatic hydrocarbon ring groups, aromatic heterocyclic groups, non-aromatic hydrocarbon ring groups or non-aromatic heterocyclic groups.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n is 3.
  • R1m”, “R2m”, “R1n”, “R2n”, “Ra”, “Rc”, na, nc, m and n are “R1m” in the general formula (1), It is synonymous with “R2m”, “R1n”, “R2n”, “Ra”, “Rc”, na, nc, m and n.
  • Ra 3 has the same meaning as “Ra”, “Rb”, and “Rc” in the general formula (1).
  • the aromatic hydrocarbon ring group, aromatic heterocyclic group, non-aromatic hydrocarbon ring group or non-aromatic heterocyclic group represented by Rz1 and Rz2 is And monovalent groups derived from an aromatic hydrocarbon ring, aromatic heterocycle, non-aromatic hydrocarbon ring or non-aromatic hydrocarbon ring represented by “Ar” in formula (1).
  • the iridium complex represented by the general formula (1) is preferably represented by the following general formula (5).
  • R1m”, “R2m”, “R1n” and “R2n” are each independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group or a non-aromatic group. It represents a hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • Ra”, “Rc” and “Ra 3 ” are each independently a hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, It represents a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • na represents an integer of 1 to 3
  • nc represents 1 or 2
  • nR3 represents an integer of 1 to 4.
  • X represents O, S, SiRz1Rz2, NRz1 or CRz1Rz2, wherein Rz1 and Rz2 are alkyl groups, aromatic hydrocarbon ring groups, aromatic heterocyclic groups, non-aromatic hydrocarbon ring groups or non-aromatic heterocyclic groups.
  • Rz1 and Rz2 are alkyl groups, aromatic hydrocarbon ring groups, aromatic heterocyclic groups, non-aromatic hydrocarbon ring groups or non-aromatic heterocyclic groups.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n is 3.
  • R1m”, “R2m”, “R1n”, “R2n”, “Ra”, “Rc”, na, nc, m and n are “R1m” in the general formula (1), It is synonymous with “R2m”, “R1n”, “R2n”, “Ra”, “Rc”, na, nc, m and n.
  • Ra 3 has the same meaning as “Ra”, “Rb”, and “Rc” in the general formula (1).
  • “X” has the same meaning as “X” in the general formula (4).
  • the iridium complex represented by the general formula (1) according to the present invention may be used in combination with a plurality of types of compounds, and phosphorescence having different structures.
  • a combination with a light emitting dopant or a combination with a fluorescent dopant may be used.
  • Host compound (2.1) Host compound represented by general formula (A)
  • the host compound according to the present invention is represented by the following general formula (A).
  • X represents NR ′, O, S, CR′R ′′ or SiR′R ′′.
  • R ′ and R ′′ each represent a hydrogen atom or a substituent.
  • Ar represents an aromatic ring.
  • n represents an integer of 0 to 8.
  • the substituents represented by R ′ and R ′′ are each an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, pentyl group).
  • X is preferably NR ′ or O
  • R ′ is an aromatic hydrocarbon group (also called an aromatic carbocyclic group, aryl group, etc., for example, phenyl group, p-chlorophenyl group, mesityl, etc.
  • aromatic hydrocarbon group and aromatic heterocyclic group may each have a substituent represented by R ′ or R ′′ in “X” of the general formula (A).
  • examples of the aromatic ring represented by “Ar” include an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
  • the aromatic ring may be a single ring or a condensed ring, and may be unsubstituted or may have a substituent represented by R ′ or R ′′ in “X” of the general formula (A).
  • the aromatic hydrocarbon ring represented by “Ar” includes a benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene ring, naphthacene ring, triphenylene Ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring, pyrene Ring, pyranthrene ring, anthraanthrene ring and the like.
  • These rings may further have substituents represented by R ′ and R ′′ in “X” of the partial structure represented by the general
  • examples of the aromatic heterocycle represented by “Ar” include a furan ring, a dibenzofuran ring, a thiophene ring, an oxazole ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, Triazine ring, benzimidazole ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring, indole ring, indazole ring, benzimidazole ring, benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, cinnoline ring , Quinoline ring, isoquinoline ring, phthalazine ring, naphthyridine ring, carbazole ring,
  • the aromatic ring represented by “Ar” is preferably a carbazole ring, carboline ring, dibenzofuran ring, or benzene ring, and more preferably carbazole.
  • the aromatic ring represented by “Ar” is preferably a condensed ring having three or more rings
  • the aromatic hydrocarbon condensed ring in which three or more rings are condensed includes: Specifically, naphthacene ring, anthracene ring, tetracene ring, pentacene ring, hexacene ring, phenanthrene ring, pyrene ring, benzopyrene ring, benzoazulene ring, chrysene ring, benzochrysene ring, acenaphthene ring, acenaphthylene ring, triphenylene ring, coronene ring , Benzocoronene ring, hexabenzocoronene ring, fluorene ring, benzofluorene ring, fluoranthene ring, perylene ring, naphthperylene ring, penta
  • aromatic heterocycle condensed with three or more rings include an acridine ring, a benzoquinoline ring, a carbazole ring, a carboline ring, a phenazine ring, a phenanthridine ring, a phenanthroline ring, a carboline ring, a cyclazine ring, Kindin ring, tepenidine ring, quinindrin ring, triphenodithiazine ring, triphenodioxazine ring, phenanthrazine ring, anthrazine ring, perimidine ring, diazacarbazole ring (any one of the carbon atoms constituting the carboline ring is a nitrogen atom Phenanthroline ring, dibenzofuran ring, dibenzothiophene ring, naphthofuran ring, naphthothiophene ring, benzodifuran ring, benzod
  • n represents an integer of 0 to 8, preferably 0 to 2, particularly preferably 1 to 2 when “X” is O or S. .
  • a low molecular compound having both a dibenzofuran ring and a carbazole ring is particularly preferable.
  • the host compound according to the present invention may be used in combination of a plurality of types of compounds.
  • the mobility (movement amount) of charges (holes and / or electrons) can be adjusted, and the light emission efficiency of the organic EL element can be improved.
  • a known host compound can be used as the host compound that may be used in combination with the host compound represented by the general formula (A).
  • the host compound that can be used in combination is not particularly limited, and compounds conventionally used in organic EL devices can be used.
  • a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
  • the known host compound 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 (polymerizable light emitting host). ), Or two or more of such compounds may be used.
  • the host compound preferably has a carbazole skeleton, a triarylamine skeleton, a thiophene skeleton, a furan skeleton, a carboline skeleton, or a diazacarbazole skeleton, and has a carbazole skeleton, a thiophene skeleton, or a furan skeleton. Is more preferable.
  • host compounds include, for example, JP-A Nos. 2001-257076, 2002-308855, 2001-313179, 2002-319491, 2001-357777, 2002. -334786, 2002-8860, 2002-334787, 2002-15871, 2002-334788, 2002-43056, 2002-334789, 2002 No. 75645, No. 2002-338579, No. 2002-105445, No. 2002-343568, No. 2002-141173, No. 2002-352957, No. 2002-203683, No. 2002-363. No. 27, No. 2002-231453, No. 2003-3165, No. 2002-234888, No. 2003-27048, No. 2002-255934, No. 2002-260861, No. 2002-280183. And host compounds described in JP-A Nos. 2002-299060, 2002-302516, 2002-305083, 2002-305084, 2002-308837 and the like.
  • the light emitting layer according to the present invention is a layer containing a light emitting dopant uniformly by being formed by a wet process.
  • the wet process is preferably film formation by a coating method such as a spin coating method, an ink jet method, or a printing method.
  • liquid medium for dissolving or dispersing the organic EL device material examples include ketones such as methyl ethyl ketone and cyclohexanone, and fatty acid esters such as ethyl acetate, isopropyl acetate, propylene glycol monomethyl ether acetate, and 3-methoxybutyl acetate.
  • Use halogenated hydrocarbons such as dichlorobenzene, aromatic hydrocarbons such as toluene, xylene, mesitylene, and cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane, and organic solvents such as DMF and DMSO.
  • a solvent having a boiling point in the range of 50 to 180 ° C. is preferably used.
  • a dispersion method it can disperse
  • the solvent content contained in the organic EL device is in the range of 0.01 to 1 ⁇ g / cm 2 .
  • the solvent content is 0.01 ⁇ g / cm 2 or less, the organic film becomes sparse, causing a high voltage when driving the element.
  • the solvent content is 1 ⁇ g / cm 2 or more, material diffusion during driving the element is caused. Or aggregation of the light emitting material, resulting in low efficiency and low driving life.
  • These solvent contents can be determined by temperature programmed desorption gas spectroscopy.
  • the organic EL device according to the present invention is a white device, not only the interaction between specific light emitting dopants but also the interaction between light emitting dopants of different wavelengths can be reduced.
  • a white element in addition to the blue phosphorescent light emitting dopant, a green light emitting dopant and a red light emitting dopant are used, but these two light emitting dopants have a long wave, that is, a long ⁇ conjugate length, Intermolecular aggregation is facilitated by the ⁇ - ⁇ interaction.
  • a hetero iridium complex is used as a short-wave blue phosphorescent light emitting dopant, there are two or four sites for stabilizing the interaction energy as compared with conventional tris isomers. It can limit and can suppress intermolecular aggregation. As a result, it is possible to reduce the energy transfer probability from the short wave luminescent dopant to the long wave green or red luminescent dopant, and to increase the amount of long wave luminescent dopants that could be doped only at low concentrations so far. Long life can be achieved.
  • the dopant-dopant interaction sites since there are six dopant-dopant interaction sites, the probability of the same molecular interaction is high, and the dopant-host interaction is dominant. In order to disperse the molecules uniformly, it was necessary to increase the mixing ratio of the host compound.
  • the interaction energy stabilization sites can be limited to two or four in comparison with conventional tris, and the dopants aggregate in a chain. Can be suppressed. As a result, the dopant can be dispersed with fewer host molecules, and the dopant compound can be doped at a high concentration.
  • the mixing molar ratio of the dopant and the host compound is preferably 1: 3 to 1: 9, more preferably 1: 4 to 1: 8, and further preferably 1: 5 to 1: 7. If the dopant concentration is less than this, the performance is not different from that of a normal tris body, which is not preferable from the viewpoint of synthetic load. On the other hand, when the concentration is higher than this, the distance between the dopant and the dopant becomes physically close, and the effect reaches a peak, which is not preferable.
  • another iridium complex (byproduct) having a different coordination ratio between the target complex (main product) and the ligand may be generated.
  • IrABB is produced as a by-product (A and B are different ligands).
  • the allowable mixing molar ratio of the main product and the by-product may be 99.95: 0.05 to 99.50: 0.50. Since the main product and the by-product have a common ligand, the emission wavelength and the HOMO-LUMO level are very close.
  • the phosphorescent light-emitting dopant having a 5-membered ring structure in the ligand of the present invention is considered to receive holes from the adjacent hole transport layer and electrons from the host molecule of the light-emitting layer in the light-emitting layer. If it is bad, the hole-excessive part will attack nearby complexes and cause decomposition. In the present invention, a very small amount of by-products are mixed in the presence of many main products, so that the LUMO level becomes stepped in part and the electron injection becomes smooth. It is thought that it is suppressing.
  • the average concentration of the luminescent dopant in the range of 0 to 10 nm from the interface with the adjacent layer is 50% or more with respect to the average concentration of all the luminescent dopants. It is preferable that a range having an average concentration of 50% or more with respect to the average concentration of all the luminescent dopants is present on the side close to the anode in the light emitting layer. Moreover, it is preferable that the molecular weight of the light emission host of the said light emitting layer is 1500 or less.
  • the range having an average concentration of 50% or more with respect to the average concentration of all luminescent dopants in the present invention is the average concentration of luminescent dopants of 50% or more with respect to the average concentration of all luminescent dopants contained in the light emitting layer. It refers to a certain range and includes that all are luminescent dopants.
  • the present invention is characterized in that the range is 0 to 5 nm from the interface with the adjacent layer, and preferably 0 to 10 nm. Even if the range which is an average concentration of 50% or more with respect to the average concentration of all the luminescent dopants contained in the light emitting layer is present on both sides of the light emitting layer near the anode and near the cathode, May be present only. When it exists only on one side, it is preferable to exist on the side close to the anode.
  • a method of drying the solvent at a high speed during coating film formation of the light-emitting layer. for example, a method of drying the solvent at a high speed during coating film formation of the light-emitting layer.
  • means for drying the solvent at high speed include using a solvent having a high vapor pressure and drying the solvent by blowing air.
  • a solvent having a high vapor pressure is a solvent having a vapor pressure at 20 ° C. of 1.0 kPa or more. Examples of such a solvent include toluene (20 ° C. vapor pressure: 2.9 kPa), ethyl acetate (20 ° C. vapor).
  • Drying the solvent by blowing is to blow and blow immediately after applying the light emitting layer, and depends on the characteristics and material purity of the host compound or luminescent dopant used, or the characteristics of the solvent used. In general, it cannot be specified. However, as long as the air temperature and the air speed do not affect the formation of the light emitting layer according to the present invention, the higher the drying speed, the faster the drying.
  • Secondary ion mass spectrometry is preferably used because it is possible and can follow the concentration change of the element in the depth direction.
  • Secondary ion mass spectrometry for example, Japanese Society of Surface Science “Secondary ion mass spectrometry (Surface Science and Technology Selection)” (Maruzen) can be referred to.
  • sputtering is performed by irradiating a sample surface with an ion beam called primary ions under a high vacuum of about 10 ⁇ 8 Pa.
  • This is a method of analyzing elements present on the surface by mass spectrometry of secondary ions in the constituent particles released thereby.
  • it is a destructive analysis in which the surface is sputtered and scraped off, it is possible to analyze the change in element concentration from the surface to a depth of ⁇ m or more.
  • metal ion species such as Cs + , In + , and Ga + are preferable. Which ion species is preferably used depends on the element to be measured.
  • ADEPT 1010 manufactured by Physical Electronics is used, the primary ion species is Cs + , and the acceleration voltage of the primary ions is 2 kV.
  • the distribution amounts of various elements in the depth direction in the organic EL element was measured.
  • the adjacent layer is a layer having a function different from that of the light emitting layer adjacent to the light emitting layer containing the host compound and the light emitting dopant, and the adjacent layer may be between the anode and the light emitting layer or between the cathode and the light emitting layer.
  • the adjacent layer is not particularly limited, but for example, a hole injection layer (anode buffer layer), an electron injection layer (cathode buffer layer), a hole blocking layer, an electron blocking layer, a hole transport layer, an electron transport layer, an intermediate layer
  • the adjacent layer is preferably an electron transport layer or a hole transport layer.
  • the light emitting layer was formed as described above, it was possible to suppress a decrease in light emission luminance and an increase in driving voltage. Although the reason is not clear, there is a factor that hinders carrier injection by setting the vicinity of the interface with the adjacent layer to an average concentration of 50% or more with respect to the average concentration of all light-emitting dopants contained in the light-emitting layer. Therefore, it is estimated that a decrease in light emission luminance and an increase in driving voltage are suppressed, and driving at a low voltage is possible.
  • two or more host compounds may be used. Combining two or more kinds of host compounds can not only prevent a decrease in light emission efficiency due to aggregation and crystallization, but also increase the recombination efficiency and improve the light emission efficiency.
  • the LUMO (or HOMO) energy levels of the respective host compounds influence, and the case where the host compound consists of a single host compound or LUMO (or HOMO)
  • the carrier trap and hopping are balanced, and it has the role of LUMO (or HOMO) that forms a pseudo wide energy band.
  • the LUMO (or HOMO) energy level of a host compound that forms a pseudo wide energy band not only facilitates carrier movement from an adjacent electron (or hole) transport layer, but also LUMO. (Or HOMO) It has a feature that carrier transfer to a plurality of phosphorescent dopants having different energy levels is facilitated. Therefore, not only can injection inhibition due to the energy barrier generated when different organic layers are joined not only be minimized, but also a problem carrier during carrier transfer from a host-injected host compound to a plurality of light-emitting dopants having different energy levels. The trap problem can be minimized, and it is excellent in that the improvement of the recombination probability and the expansion of the recombination region can simultaneously improve the light emission efficiency and extend the lifetime.
  • the absolute values of the LUMO (or HOMO) energy levels of these two or more host compounds are not particularly limited, but the difference between the absolute values of the respective LUMO energy levels is 0.1 to 1.0 eV. Preferably, it is 0.2 to 1.0 eV.
  • the difference in the absolute value of the LUMO energy level is smaller than 0.1 eV, the effect of improving the recombination probability is small, and when it is larger than 1.0 eV, the charge injection efficiency is adversely affected. Can be considered.
  • a plurality of host molecules having different molecular van der Waals volumes may be mixed with the molecular van der Waals volume of the luminescent dopant.
  • the recombination probability and hence the luminous efficiency differed, and it was difficult to adjust the emission color and the color change after the lifetime, but different molecular van der Waals between the emission dopant molecules. It is considered that the above problem can be solved by interposing a plurality of host compounds having a volume.
  • the difference in the molecular van der Waals volume between the host compounds is at least 10 3 or more.
  • the molecular van der Waals volume refers to a volume inside the surface of the molecule when the atoms constituting the molecule are replaced with spheres having van der Waals radii and the spheres are arranged in the form of molecules.
  • van der Waals distance the equilibrium molecular spacing in molecular crystals, that is, the molecular spacing at the minimum point of the potential curve of intermolecular interaction, is called van der Waals distance, but very large force is required to bring the two molecules within the distance. I need. In this sense, it is reasonable to consider a molecule as a rigid body with a certain volume and shape, and it is generally assumed that each atom in the molecule occupies a spherical volume with a specific radius. Therefore, the radius inherent to these atoms is called the van der Waals radius.
  • a method of mixing a plurality of these host compounds is effective for a single color light emitting device, but is particularly suitable for a white light emitting device including a plurality of light emitting dopants having different emission wavelengths.
  • the molecular van der Waals volumes of the luminescent dopant and the host compound are values obtained by molecular orbital calculation support software “Tencube / WM”.
  • LUMO is the lowest unoccupied molecular orbital of a compound.
  • the LUMO energy level is energy in which electrons in the vacuum level fall to the LUMO of the compound and stabilize, and are defined as energy when the vacuum level is zero.
  • HOMO is the highest occupied molecular orbital of a compound.
  • the HOMO energy level is defined by a value obtained by multiplying the energy required to move the electrons in the HOMO to the vacuum level by “ ⁇ 1”.
  • the values of the HOMO energy level and the LUMO energy level are determined by Gaussian 98 (Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, software for molecular orbital calculation manufactured by Gaussian, USA). , Inc., Pittsburgh PA, 2002.) and is defined as a value (eV unit converted value) calculated by performing structural optimization using B3LYP / LanL2DZ as a keyword. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
  • the inventors of the present invention found that the molecular weight of the host compound in the formation of the light-emitting layer is particularly low in the slope of the Guinier plot of the scattered light due to the low-molecular-weight organic substance in the X-ray small angle scattering measurement of the light-emitting layer after coating film formation
  • the molecular weight of the low molecular weight organic substance, particularly the host compound, in the light emitting layer is preferably in the range of 400 to 2000, more preferably in the range of 400 to 800.
  • “Molecular weight” as used herein is obtained using a conventionally known mass spectrum. For polymers (for example, those having a molecular weight of 10,000 or more), a conventionally known GPC (gel permeation chromatography) is used. It is measured.
  • a general-purpose device such as a nanoscale X-ray structure evaluation device NANO-Viewer manufactured by Rigaku Corporation may be used, preferably KEK / PF, SP-ring8,
  • An X-ray small angle scattering device using a large synchrotron radiation facility such as SAGA-LS can be used. The measurement conditions are shown below.
  • the thin film sample was irradiated at a wavelength of 1 mm using SP-ring 8 radiation as X-rays.
  • the measurement uses a HUBER multi-axis diffractometer, the X-ray incident angle ⁇ is fixed at 0.2 °, and the thin film sample is irradiated.
  • the detector uses a scintillation counter to measure scattered radiation from 1 to 43 °. went.
  • the particle size / hole size analysis software NANO-Solver manufactured by Rigaku Corporation was used for analysis of the obtained X-ray small angle scattering data.
  • a part is scattered by an electron cloud of each atom constituting the X-ray.
  • the scattering vector q is generally used instead of the scattering angle ⁇ . q is given by the following formula (i).
  • the small region of q is called the Guinier region, and the large region is called the Porod region. From the former, larger spatial information, particle dispersion state and long-period structure, from the latter, smaller region information, high It is possible to obtain molecular polymerization state, surface shape of dispersed particles, protein structural analysis, and the like.
  • I (q) I (0) exp ( ⁇ q ⁇ 2 * Rg ⁇ 2/3) (ii)
  • I (q) represents the scattering intensity
  • Rg represents the radius of inertia.
  • This equation is called Guinier's law, and when the scattering intensity I (q) is plotted against q ⁇ 2, the inclination depends on the inertia radius of the scatterer. That is, information on the size of aggregated clusters and voids having different molecular densities in the film is included. In general, it is known that when the particles of the scatterer are small and uniformly dispersed, the slope of this Guinier plot becomes gentle, and when the particles are knitted large, the slope becomes steep.
  • the hole injection layer (also referred to as “anode buffer layer”) according to the present invention is a layer provided between the anode and the light emitting layer in order to lower the driving voltage and improve the light emission luminance. It is described in detail in Volume 2, Chapter 2, “Electrode Materials” (pages 123 to 166) of “The Forefront of Industrialization (issued by NTT Corporation on November 30, 1998)”.
  • the hole injection layer is provided as necessary, and may be present between the anode and the light emitting layer or between the anode and the hole transport layer as described above.
  • the details of the hole injection layer are described in JP-A-9-45479, JP-A-9-260062, JP-A-8-288069, etc.
  • Examples of the material used for the hole injection layer include: Examples thereof include materials used for the hole transport layer described later.
  • phthalocyanine derivatives represented by copper phthalocyanine, hexaazatriphenylene derivatives as described in JP-T-2003-519432, JP-A-2006-135145, etc.
  • metal oxides represented by vanadium oxide metal oxides represented by vanadium oxide
  • amorphous Conductive polymers such as carbon, polyaniline (emeraldine) and polythiophene, orthometalated complexes represented by tris (2-phenylpyridine) iridium complex, and triarylamine derivatives are preferred.
  • the materials used for the hole injection layer may be used alone or in combination of two or more.
  • the electron injection layer (also referred to as “cathode buffer layer”) according to the present invention is a layer provided between the cathode and the light emitting layer for the purpose of lowering the driving voltage and improving the light emission luminance. It is described in detail in Chapter 2 “Electrode Materials” (pages 123 to 166) of the second edition of “The Forefront of Industrialization (issued by NTT Corporation on November 30, 1998)”.
  • the electron injection layer is provided as necessary, and may be present between the cathode and the light emitting layer or between the cathode and the electron transport layer as described above.
  • the electron injection layer is preferably a very thin film, and the film thickness is preferably in the range of 0.1 to 5 nm, depending on the material. Moreover, the nonuniform film
  • Metals typified by strontium and aluminum alkali metal compounds typified by lithium fluoride, sodium fluoride, potassium fluoride, etc., alkaline earth metal compounds typified by magnesium fluoride, calcium fluoride, etc., oxidation Examples thereof include metal oxides typified by aluminum, metal complexes typified by lithium 8-hydroxyquinolate (Liq), and the like.
  • the below-mentioned electron transport material it is also possible to use the below-mentioned electron transport material.
  • the material used for said electron injection layer may be used independently, and may be used in combination of multiple types.
  • the hole blocking layer is a layer having the function of an electron transport layer in a broad sense, and is preferably made of a material having a function of transporting electrons and a small ability to transport holes. By blocking the holes, the probability of recombination of electrons and holes can be improved. Moreover, the structure of the electron carrying layer mentioned later can be used as a hole-blocking layer concerning this invention as needed.
  • the hole blocking layer provided in the organic EL device of the present invention is preferably provided adjacent to the cathode side of the light emitting layer.
  • the thickness of the hole blocking layer according to the present invention is preferably in the range of 3 to 100 nm, more preferably in the range of 5 to 30 nm.
  • the material used for a hole-blocking layer the material used for the below-mentioned electron carrying layer is used preferably, and the material used as the above-mentioned host compound is also preferably used for a hole-blocking layer.
  • the electron blocking layer is a layer having a function of a hole transport layer in a broad sense, and is preferably made of a material having a function of transporting holes and a small ability to transport electrons, while transporting holes. By blocking electrons, the probability of recombination of electrons and holes can be improved. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer concerning this invention as needed.
  • the electron blocking layer provided in the organic EL device of the present invention is preferably provided adjacent to the anode side of the light emitting layer.
  • the thickness of the electron blocking layer according to the present invention is preferably in the range of 3 to 100 nm, more preferably in the range of 5 to 30 nm.
  • a material used for the electron blocking layer a material used for a hole transport layer described later is preferably used, and a material used as the above-described host compound is also preferably used for the electron blocking layer.
  • the hole transport layer is made of a material having a function of transporting holes and may have a function of transmitting holes injected from the anode to the light emitting layer.
  • the total thickness of the hole transport layer of the present invention is not particularly limited, but is usually in the range of 5 nm to 5 ⁇ m, more preferably 2 to 500 nm, and further preferably 5 to 200 nm.
  • the material used for the hole transport layer may have any of the hole injection property or the transport property and the electron barrier property. Any one can be selected and used.
  • a hole transport material may have any of the hole injection property or the transport property and the electron barrier property. Any one can be selected and used.
  • triarylamine derivatives examples include a benzidine type typified by ⁇ NPD, a starburst type typified by MTDATA, and a compound having fluorene or anthracene in the triarylamine linking core part.
  • hexaazatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as hole transport materials.
  • a hole transport layer having a high p property doped with impurities can also be used.
  • Examples thereof include JP-A-4-297076, JP-A-2000-196140, and JP-A-2001-102175. Appl. Phys. 95, 5773 (2004), and the like. JP-A-11-251067, J. Pat. Huang et. al. It is also possible to use so-called p-type hole transport materials and inorganic compounds such as p-type-Si and p-type-SiC, as described in the literature (Applied Physics Letters 80 (2002), p. 139). Further, ortho-metalated organometallic complexes having Ir or Pt as a central metal as typified by Ir (ppy) 3 are also preferably used.
  • the above-mentioned materials can be used as the hole transport material, a triarylamine derivative, carbazole derivative, indolocarbazole derivative, azatriphenylene derivative, organometallic complex, aromatic amine is introduced into the main chain or side chain.
  • the polymer materials or oligomers used are preferably used.
  • the electron transport layer is made of a material having a function of transporting electrons, and may have a function of transmitting electrons injected from the cathode to the light emitting layer.
  • the total thickness of the electron transport layer of the present invention is not particularly limited, but is usually in the range of 2 nm to 5 ⁇ m, more preferably 2 to 500 nm, and further preferably 5 to 200 nm.
  • the organic EL element when the light generated in the light emitting layer is extracted from the electrode, the light extracted directly from the light emitting layer interferes with the light extracted after being reflected by the electrode from which the light is extracted and the electrode located at the counter electrode. It is known to wake up.
  • the electron mobility of the electron transport layer is preferably 10 ⁇ 5 cm 2 / Vs or more, particularly when the thickness is large. .
  • the material used for the electron transporting layer may be any of electron injecting or transporting properties and hole blocking properties, and can be selected from conventionally known compounds. Can be selected and used.
  • a nitrogen-containing aromatic heterocyclic derivative (carbazole derivative, azacarbazole derivative (one or more of carbon atoms constituting the carbazole ring is substituted with a nitrogen atom), pyridine derivative, pyrimidine derivative, pyrazine derivative, pyridazine derivative, Triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, azatriphenylene derivatives, oxazole derivatives, thiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, triazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, etc.), dibenzofuran derivatives, And dibenzothiophene
  • 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.
  • a distyrylpyrazine derivative used as a material for the light-emitting layer can also be used as an electron transport material, and an inorganic material such as n-type-Si, n-type-SiC, etc., like the hole injection layer and the hole transport layer.
  • a semiconductor 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.
  • the electron transport layer may be doped with a doping material as a guest material to form an electron transport layer having a high n property (electron rich).
  • the doping material include n-type dopants such as metal complexes and metal compounds such as metal halides.
  • Specific examples of the electron transport layer having such a structure include, for example, JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J. Pat. Appl. Phys. , 95, 5773 (2004) and the like.
  • More preferable electron transport materials in the present invention include pyridine derivatives, pyrimidine derivatives, pyrazine derivatives, triazine derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, carbazole derivatives, azacarbazole derivatives, and benzimidazole derivatives.
  • An electron transport material may be used independently and may be used in combination of multiple types.
  • an electrode material made of a metal, an alloy, an electrically conductive compound and a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode substances include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • 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.
  • wet film-forming methods such as a printing system and a coating system, can also be used.
  • the transmittance be greater than 10%
  • the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually in the range of 10 to 1000 nm, preferably in the range of 10 to 200 nm.
  • Cathode 8 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 within the range of 10 nm to 5 ⁇ m, preferably within the range of 50 to 200 nm.
  • the light emission luminance is improved, which is convenient.
  • a transparent or translucent cathode can be prepared by forming the above metal on the cathode with a film thickness in the range of 1 to 20 nm and then forming the conductive transparent material mentioned in the description of the anode thereon.
  • an element in which both the anode and the cathode are transmissive can be manufactured.
  • the 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 is not particularly limited in the type of glass, plastic, etc., and is transparent. Or 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 and cellulose nitrate or their derivatives, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide, polyether Sulfone (PES), polyphenylene sulfide, polysulfones, poly -Cycloolefin resins such as etherimide, polyether ketone imide, polyamide, fluororesin, nylon, polymethyl methacrylate, acrylic or polyarylate, Arton (trade name, manufactured by JSR) or Appel
  • the surface of the resin film may be formed with an inorganic film, an organic film, or a hybrid film of both, and 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 oxygen measured by a method according to JIS K 7126-1987.
  • a high barrier film having a permeability of 10 ⁇ 3 cm 3 / (m 2 ⁇ 24 h ⁇ atm) or less and a water vapor permeability of 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less is preferable. More preferably, the transmittance is 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less.
  • 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 cm 3 / (m 2 ⁇ 24 h ⁇ atm) or less, and conforms to JIS K 7129-1992.
  • the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) measured by the above method is preferably 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.
  • fever and chemical curing types (two liquid mixing), such as an epoxy type, can be mentioned.
  • 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. Further, a desiccant may be dispersed in the adhesive. Application
  • coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.
  • the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
  • the material for forming the film may be any material that has a function of suppressing infiltration 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.
  • a vacuum can also be used.
  • a hygroscopic compound can also be enclosed inside.
  • hygroscopic compound examples include metal oxides (eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide), sulfates (eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
  • metal oxides eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
  • sulfates eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate.
  • metal halides for example, calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide, etc.
  • perchloric acids for example, perchloric acid
  • Barium, magnesium perchlorate, etc. and the like, and 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 or the sealing film on the side facing the support substrate with the organic layer interposed therebetween.
  • 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, etc. used for sealing can be used. It is preferable to use it.
  • the organic EL element emits light inside a layer having a higher refractive index than air (with a refractive index in the range of 1.7 to 2.1), and about 15% to 20% of the light generated in the light emitting layer. It is generally said that only light can be extracted. 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 for improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate to prevent total reflection at the interface between the transparent substrate and the air (US Pat. No. 4,774,435), condensing on the substrate.
  • a method of improving the efficiency by imparting a property Japanese Patent Laid-Open No. 63-314795
  • a method of forming a reflective surface on the side surface of the element Japanese Patent Laid-Open No. 1-220394
  • Japanese Patent Laid-Open No. 1-220394 Japanese Patent Laid-Open No. 1-220394
  • Japanese Patent Laid-Open No. 1-220394 Japanese Patent Laid-Open No. 1-220394
  • Japanese Patent Laid-Open No. 2001-202827 Japanese Patent Laid-Open No. 2001-202827
  • Japanese Patent Laid-Open No. 11-283951 Japanese Patent Laid-Open No. 11-283951
  • 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 in the range of 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.
  • Bragg diffraction such as first-order diffraction and second-order diffraction.
  • light that cannot go out due to total reflection between layers, etc. is diffracted by introducing a diffraction grating into any layer or medium (inside a transparent substrate or transparent electrode). 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. However, by making the refractive index distribution a two-dimensional distribution, light traveling in all directions is diffracted, and 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 in the range of 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 electroluminescence device of the present invention is processed to provide, for example, a microlens array-like structure on the light extraction side of the support substrate, or is combined with a so-called condensing sheet, for example, in a specific direction. Condensing light in the front direction with respect to the light emitting surface can increase the luminance in a specific direction.
  • a quadrangular pyramid having a side of 30 ⁇ m and an apex angle of 90 degrees is arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably within a range of 10 to 100 ⁇ m. If it is smaller than this, the effect of diffraction is generated and colored, and if it is too large, the thickness becomes thick, which is not preferable.
  • 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 with 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 in the range of 10 to 200 nm. Is made.
  • the organic compound layer containing the iridium complex represented by formula (A) and the host compound represented by the general formula (A) is formed by a wet process and is particularly preferably used for forming a light emitting layer.
  • the materials can be mixed at an arbitrary ratio, and a wet process is preferable from the viewpoint that pinholes are not easily generated.
  • Film formation by a coating method such as an inkjet method or a printing method is preferable.
  • 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 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 in the range of 2 to 40 V with the anode being + and the cathode being-.
  • An alternating voltage may be applied.
  • the alternating current waveform to be applied may be arbitrary.
  • the organic EL element of the present invention can be used as a display device, a display, and various light emission sources.
  • lighting devices home lighting, interior lighting
  • clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light
  • the light source of a sensor etc. are mentioned, It is not limited to this, Especially, it can use effectively for the use as a backlight of a liquid crystal display device, and a light source for illumination.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like as needed during film formation. In the case of 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. In the fabrication of the element, a conventionally known method is used. Can do.
  • a gas barrier film having a thickness of 500 nm and having an oxygen permeability of 0.001 cm 3 / (m 2 ⁇ 24 h) or less and a water vapor permeability of 0.001 g / (m 2 ⁇ 24 h) or less is flexible.
  • a conductive film was prepared.
  • ITO indium tin oxide
  • each light-emitting layer composition having the following composition was formed by spin coating at 1500 rpm for 30 seconds, and then held at 120 ° C. for 30 minutes to form a light-emitting layer with a thickness of 50 nm. did.
  • a sealing member As a sealing member, a flexible aluminum foil (made by Toyo Aluminum Co., Ltd.) having a thickness of 30 ⁇ m, a polyethylene terephthalate (PET) film (12 ⁇ m thickness) and an adhesive for dry lamination (two-component reaction type urethane) (Adhesive layer thickness 1.5 ⁇ m) was used.
  • PET polyethylene terephthalate
  • Adhesive layer thickness 1.5 ⁇ m Adhesive layer thickness 1.5 ⁇ m
  • thermosetting adhesive was uniformly applied to the aluminum surface as a sealing adhesive with a thickness of 20 ⁇ m along the adhesive surface (glossy surface) of the aluminum foil using a dispenser. This was dried under a vacuum of 100 Pa or less for 12 hours. Furthermore, it moved to a nitrogen atmosphere with a dew point temperature of ⁇ 80 ° C. or lower and an oxygen concentration of 0.8 ppm, dried for 12 hours or longer, and adjusted the water content of the sealing adhesive to 100 ppm or lower.
  • an epoxy adhesive mixed with the following (A) to (C) was used as the thermosetting adhesive.
  • the sealing substrate is closely attached and arranged so as to cover the joint portion between the extraction electrode and the electrode lead, and the thickening condition, the pressure roll temperature of 120 ° C., the pressure of 0.5 MPa, and the apparatus using the pressure roll Sample 1 was manufactured by tightly sealing at a speed of 0.3 m / min.
  • ⁇ Colorless and transparent, no precipitation ⁇ : Some particles are seen in the coating solution container, but dissolves without any problem as soon as re-stirring ⁇ : Grains are confirmed in the coating solution container, and re-stirring must be continued for 5 minutes or more ⁇ : The coating solution becomes cloudy and does not dissolve at all even after re-stirring.
  • the organic EL element of the present invention is useful when used in a display device and a lighting device.
  • the samples 2-1 and 2-2 of the present invention were compared with the samples 2-3 and 2-4 of the comparative examples, the deposition of the device material, the solvent content, the luminous efficiency, the driving voltage It is clear that the lifetime is excellent.
  • the present invention can be used particularly suitably to provide an organic EL device that suppresses aggregation and crystallization of luminescent dopants and is excellent in driving voltage, luminous efficiency, luminous lifetime, and solubility.

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  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un élément EL organique (100) comportant, disposée entre une électrode positive (2) et une électrode négative (8), au moins une couche organique composée comprenant une couche (5) émettant de la lumière. Au moins une couche de la couche organique composée est formée à l'aide d'un processus par voie humide et comprend un complexe d'iridium indiqué par la formule générale (1) et un complexe hôte indiqué par la formule générale (A).
PCT/JP2013/061538 2012-05-09 2013-04-18 Élément à électroluminescence organique, procédé de production d'un élément à électroluminescence organique, dispositif d'affichage et dispositif d'éclairage WO2013168534A1 (fr)

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KR101739024B1 (ko) * 2015-07-27 2017-05-24 희성소재 (주) 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
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CN107840835A (zh) * 2016-09-19 2018-03-27 株式会社Lg化学 新的杂环化合物及利用它的有机发光元件
WO2018139767A1 (fr) * 2017-01-26 2018-08-02 주식회사 엘지화학 Nouveau composé à base d'amine et dispositif électroluminescent organique l'utilisant
KR20180088262A (ko) * 2017-01-26 2018-08-03 주식회사 엘지화학 신규한 아민계 화합물 및 이를 이용한 유기발광 소자
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CN111747938A (zh) * 2020-07-03 2020-10-09 长春海谱润斯科技有限公司 一种芳胺化合物及其有机电致发光器件
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US9847501B2 (en) 2011-11-22 2017-12-19 Idemitsu Kosan Co., Ltd. Aromatic heterocyclic derivative, material for organic electroluminescent element, and organic electroluminescent element
JPWO2015087795A1 (ja) * 2013-12-10 2017-03-16 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、照明装置及び表示装置
WO2015087795A1 (fr) * 2013-12-10 2015-06-18 コニカミノルタ株式会社 Élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage
US9780312B2 (en) 2014-10-17 2017-10-03 Samsung Electronics Co., Ltd. Carbazole-based compound and organic light emitting device including the same
WO2016143508A1 (fr) * 2015-03-06 2016-09-15 コニカミノルタ株式会社 Élément électroluminescent organique et matériau d'élément électroluminescent organique
JPWO2016143508A1 (ja) * 2015-03-06 2017-12-14 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子及び有機エレクトロルミネッセンス素子材料
KR101739024B1 (ko) * 2015-07-27 2017-05-24 희성소재 (주) 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
WO2017018795A3 (fr) * 2015-07-27 2017-05-11 희성소재(주) Composé hétérocyclique et diode électroluminescente organique utilisant ce composé
CN107922837A (zh) * 2015-07-27 2018-04-17 喜星素材株式会社 杂环化合物和使用其的有机发光二极管
CN107922837B (zh) * 2015-07-27 2021-02-26 Lt素材株式会社 杂环化合物和使用其的有机发光二极管
US10381577B2 (en) 2015-07-27 2019-08-13 Heesung Material Ltd. Hetero-cyclic compound and organic light emitting device using the same
JP2018522898A (ja) * 2015-07-27 2018-08-16 ヒソン・マテリアル・リミテッドＨｅｅｓｕｎｇ Ｍａｔｅｒｉａｌ Ｌｔｄ． ヘテロ環化合物およびこれを用いた有機発光素子
WO2017090918A1 (fr) * 2015-11-02 2017-06-01 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique le comprenant
CN108290836A (zh) * 2015-11-02 2018-07-17 德山新勒克斯有限公司 有机电子元件用化合物、利用该化合物的有机电子元件及其电子装置
KR20170057660A (ko) * 2015-11-17 2017-05-25 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 전자 소자
KR101991428B1 (ko) * 2015-11-17 2019-06-20 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 전자 소자
CN107840835B (zh) * 2016-09-19 2021-08-31 株式会社Lg化学 新的杂环化合物及利用它的有机发光元件
CN107840835A (zh) * 2016-09-19 2018-03-27 株式会社Lg化学 新的杂环化合物及利用它的有机发光元件
KR101967383B1 (ko) * 2017-01-26 2019-04-10 주식회사 엘지화학 신규한 아민계 화합물 및 이를 이용한 유기발광 소자
KR20180088262A (ko) * 2017-01-26 2018-08-03 주식회사 엘지화학 신규한 아민계 화합물 및 이를 이용한 유기발광 소자
CN109803966B (zh) * 2017-01-26 2022-06-10 株式会社Lg化学 新的基于胺的化合物和使用其的有机发光器件
CN109803966A (zh) * 2017-01-26 2019-05-24 株式会社Lg化学 新的基于胺的化合物和使用其的有机发光器件
WO2018139767A1 (fr) * 2017-01-26 2018-08-02 주식회사 엘지화학 Nouveau composé à base d'amine et dispositif électroluminescent organique l'utilisant
US11261176B2 (en) 2017-01-26 2022-03-01 Lg Chem, Ltd. Amine-based compound and organic light emitting device using the same
US11081655B2 (en) 2017-04-13 2021-08-03 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device using the same
US11518769B2 (en) 2017-07-20 2022-12-06 Lg Chem, Ltd. Heterocyclic compounds and organic light emitting device using the same
US11578076B2 (en) 2017-07-20 2023-02-14 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device using the same
US11840538B2 (en) 2017-07-20 2023-12-12 Lg Chem, Ltd. Heterocyclic compounds and organic light emitting device using the same
CN111320614B (zh) * 2018-12-14 2023-11-03 乐金显示有限公司 具有优异的耐热性和发光性的有机化合物、具有该化合物的有机发光二极管和有机发光装置
CN111320614A (zh) * 2018-12-14 2020-06-23 乐金显示有限公司 具有优异的耐热性和发光性的有机化合物、具有该化合物的有机发光二极管和有机发光装置
US11683982B2 (en) 2018-12-14 2023-06-20 Lg Display Co., Ltd. Organic compound having excellent thermal resistance property and luminescent property, organic light emitting diode and organic light emitting device having the compound
CN111747938A (zh) * 2020-07-03 2020-10-09 长春海谱润斯科技有限公司 一种芳胺化合物及其有机电致发光器件
US20230107826A1 (en) * 2020-12-28 2023-04-06 Boe Technology Group Co., Ltd. Organic Light Emitting Device and Display Apparatus

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