WO2016056562A1 - Complexe d'iridium, matériau électroluminescent organique, élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage - Google Patents

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

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WO2016056562A1
WO2016056562A1 PCT/JP2015/078371 JP2015078371W WO2016056562A1 WO 2016056562 A1 WO2016056562 A1 WO 2016056562A1 JP 2015078371 W JP2015078371 W JP 2015078371W WO 2016056562 A1 WO2016056562 A1 WO 2016056562A1
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atom
iridium complex
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general formula
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大津　信也
北　弘志
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コニカミノルタ株式会社
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials

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  • the present invention relates to an iridium complex, an organic electroluminescence material using the iridium complex, an organic electroluminescence element, and a display device and an illumination device provided with the organic electroluminescence element. More specifically, the present invention relates to an iridium complex having improved luminous efficiency and durability.
  • An organic electroluminescence element (hereinafter also referred to as an organic EL element) has a configuration in which a light emitting layer containing a light emitting compound is sandwiched between a cathode and an anode, and is injected from the anode by applying an electric field.
  • a light emitting device that utilizes excitons (excitons) by recombining electrons injected from holes and cathodes in the light emitting layer, and light emission (fluorescence / phosphorescence) when the excitons are deactivated It is.
  • An organic EL element is an all-solid-state element composed of an organic material film having a thickness of only a submicron between electrodes, and can emit light at a voltage of about several volts to several tens of volts. Therefore, it is expected to be used for next-generation flat display and lighting.
  • organic EL elements As for the development of organic EL elements for practical application, Princeton University has reported on organic EL elements that use phosphorescence from excited triplets, and since then, research on materials that exhibit phosphorescence at room temperature has become active. It is coming. In addition, organic EL elements that utilize phosphorescence emission can in principle achieve a light emission efficiency that is approximately four times that of organic EL elements that utilize fluorescence emission. Research and development of device layer configurations and electrodes are performed all over the world. For example, many compounds have been studied focusing on heavy metal complexes such as iridium complexes. As described above, the phosphorescence emission method is a method having a very high potential.
  • an organic EL element using phosphorescence emission is greatly different from an organic EL element using fluorescence emission, and the position of the emission center is controlled.
  • the method, particularly how to recombine within the light emitting layer and how to stably emit light, is an important technical issue in improving the efficiency and lifetime of the device.
  • the luminous efficiency is determined by the ratio of the radiation speed that transitions with light emission to the non-radiative transition that transitions with heat. It is known that there is a close connection between the non-radiative transition and the structural change of the phosphorescent compound. That is, when a large structural change occurs, the transition occurs with heat, and the light emission efficiency decreases (for example, see Non-Patent Document 1).
  • the phosphorescent compound is composed of a transition metal and a ligand.
  • a ligand for example, a compound in which an aromatic heterocycle and an aromatic ring (or aromatic heterocycle) are connected by a single bond (hereinafter, also referred to as a biaryl-type ligand) is often used. It is considered that the main cause of the increase in transition is a structural change of the biaryl type ligand. Specifically, the aromatic ring and aromatic heterocycle (or two aromatic heterocycles) constituting the biaryl-type ligand coordinated with the transition metal are bonded with a single bond, Structural changes occur and non-radiative transitions increase.
  • the present invention has been made in view of the above-described problems and circumstances, and the problem to be solved is an iridium complex with improved luminous efficiency and durability, an organic electroluminescent material using the iridium complex, an organic electroluminescent element, and the organic It is to provide a display device and a lighting device provided with an electroluminescence element.
  • the present inventor is that the bidentate ligand of the iridium complex has a hydrogen bond in the ligand and immobilizes the structure in the process of examining the cause of the above-mentioned problem.
  • the present invention has been achieved. That is, the said subject which concerns on this invention is solved by the following means.
  • An iridium complex having a bidentate ligand containing an aromatic heterocycle The bidentate ligand is a ligand in which the aromatic heterocycle and another aromatic heterocycle or aromatic ring are bonded by a single bond, and has a hydrogen bond in the ligand.
  • a 1 and A 2 each represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a 3 represents an aromatic heterocyclic ring.
  • X 1 , X 5 , X 1a and X 5a represents a nitrogen atom or a carbon atom
  • X 2 to X 4 each represents a nitrogen atom, a carbon atom, an oxygen atom, or a sulfur atom
  • X 6 represents an oxygen atom, a nitrogen atom, a sulfur atom
  • Ra represents a hydrogen atom, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkyl group or a cycloalkyl group
  • n represents 0 or 1
  • l represents Represents 1 to 3.
  • m represents 0 to 2.
  • l + m 3)
  • the iridium complex according to any one of items 1 to 3, wherein the iridium complex has a partial structure represented by the following general formula (2).
  • a 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a 3 represents an aromatic heterocyclic ring containing X 1a and X 5a.
  • a 4 represents X 6 .
  • X 1 , X 5 , X 1a and X 5a each represent a nitrogen atom or a carbon atom
  • X 2 to X 4 represent a nitrogen atom, a carbon atom, an oxygen atom or a sulfur atom, respectively.
  • X 6 represents an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a silicon atom
  • X 7 and X 8 represent CRc and N
  • Rc represents a hydrogen atom or a substituent
  • ns represents 0 or 1 represents 1.
  • l represents 1 to 3.
  • m represents 0 to 2.
  • l + m 3.
  • the iridium complex according to any one of items 1 to 3, wherein the iridium complex has a partial structure represented by the following general formula (3).
  • a 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a 3 represents an aromatic heterocyclic ring.
  • X 1 , X 5 , X 1a and X 5a are each represented by X 2 to X 4 each represent a nitrogen atom, a carbon atom, an oxygen atom, or a sulfur atom
  • X 6 represents an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, or a silicon atom.
  • Ra represents a hydrogen atom, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkyl group or a cycloalkyl group
  • R 1 represents an electron withdrawing group
  • n is 0 or 1
  • L represents 1 to 3.
  • m represents 0 to 2.
  • l + m 3.
  • a 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a 3 represents an aromatic heterocyclic ring.
  • X 1 , X 5 , X 1a and X 5a are each represented by X 2 to X 4 each represent a nitrogen atom, a carbon atom, an oxygen atom, or a sulfur atom, and
  • X 6 represents an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, or a silicon atom.
  • Ra represents a hydrogen atom, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkyl group or a cycloalkyl group
  • R 2 represents an electron donating group
  • n is 0 or 1
  • L represents 1 to 3.
  • m represents 0 to 2.
  • l + m 3.
  • iridium complex according to any one of items 1 to 3, wherein the iridium complex has a partial structure represented by the following general formula (5).
  • V represents a trivalent linking group. It is linked to L 1 , L 2 and L 3 by a covalent bond.
  • L 1 to L 3 are each represented by the following general formula (6).
  • X 1 represents a nitrogen atom or a carbon atom.
  • X 2 to X 4 each represent a nitrogen atom, a carbon atom, an oxygen atom, or a sulfur atom.
  • X 6 represents an oxygen atom
  • Ra represents a hydrogen atom, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkyl group or a cycloalkyl group
  • n is 0 or 1 represents *. * Represents a binding site to V.
  • An organic electroluminescent material comprising the iridium complex according to any one of items 1 to 10.
  • An organic electroluminescence device having at least a light emitting layer between an anode and a cathode, The said light emitting layer contains the organic electroluminescent material of 11th term
  • a display device comprising the organic electroluminescence element according to item 12.
  • An illuminating device comprising the organic electroluminescence element according to item 12.
  • an iridium complex with improved luminous efficiency and durability an organic electroluminescent material using the iridium complex, an organic electroluminescent element, and a display device and an illumination device including the organic electroluminescent element. be able to.
  • the expression mechanism or action mechanism of the effect of the present invention is not clear, but is presumed as follows.
  • the overall structure of the iridium complex (hereinafter also referred to as an Ir complex) can be changed. It was possible to suppress the fluctuation in the film constituting the light emitting layer, and to suppress the association / aggregation of the dopants. As a result, the non-radiative transition can be reduced, the light-emitting property of the organic EL element using the iridium complex is improved, and it is presumed that the voltage increase during driving can be suppressed.
  • the iridium complex used for an organic EL element it is common to make it react with a ligand using iridium chloride. In this reaction, hydrochloric acid is generated as a by-product. Therefore, when the ligand contains, for example, imidazole, if H is present at the N-position of imidazole, charge exchange occurs between H and Cl, such as formation of hydrochloride. Therefore, it is difficult to synthesize an Ir complex unless some substituent such as a methyl group is introduced at the N position. Therefore, even if H is present at the N position, it was found that by introducing an intramolecular hydrogen bond in the ligand, exchange of charge with hydrochloric acid as a reaction by-product is eliminated, and an Ir complex can be produced. .
  • the iridium complex of the present invention is an iridium complex having a bidentate ligand containing an aromatic heterocycle, wherein the bidentate ligand is the aromatic heterocycle and another aromatic heterocycle or aromatic ring. Is a ligand bonded by a single bond, and has a hydrogen bond in the ligand. This feature is a technical feature common to the inventions according to claims 1 to 14.
  • the dissociation energy of the hydrogen atom forming the hydrogen bond is preferably 390 kJ / mol or less because it is a hydrogen bond that can suppress the structural change of the ligand.
  • the hydrogen atom forming the hydrogen bond is a nitrogen atom, an oxygen atom, a phosphorus atom, or a silicon atom because a strong hydrogen bond is formed.
  • the iridium complex has a partial structure represented by the general formula (1) from the viewpoint of manifesting the effect of the present invention.
  • the ring formed by X 1 to X 5 in the iridium complex is preferably an imidazole ring or a triazole ring. Thereby, the radiation speed can be increased.
  • a 1 in the iridium complex is preferably a benzene ring. Thereby, the radiation speed can be increased.
  • the iridium complex has a partial structure represented by the general formula (2) from the viewpoint of manifesting the effect of the present invention.
  • the iridium complex has a partial structure represented by the general formula (3) from the viewpoint of manifesting the effect of the present invention.
  • the iridium complex has a partial structure represented by the general formula (4) from the viewpoint of manifesting the effect of the present invention.
  • the iridium complex has a partial structure represented by the general formula (5) from the viewpoint of manifesting the effect of the present invention.
  • the organic electroluminescent material of the present invention is characterized by containing the iridium complex of the present invention. Thereby, an organic EL material with improved luminous efficiency and durability can be obtained.
  • the organic electroluminescent device of the present invention is an organic electroluminescent device having at least a light emitting layer between an anode and a cathode, and the light emitting layer contains the organic electroluminescent material of the present invention. To do. Thereby, the organic EL element which improved luminous efficiency and durability can be obtained.
  • the organic electroluminescence element of the present invention can be suitably provided in a display device. Thereby, luminous efficiency and durability can be improved.
  • the organic electroluminescence element of the present invention can be suitably provided in a lighting device. Thereby, luminous efficiency and durability can be improved.
  • the luminous efficiency of the phosphorescent compound is determined by the ratio of the radiative transition that transitions with light emission to the non-radiative transition that transitions with heat. It is known that the non-radiative transition and the structural change of the phosphorescent compound have a close connection, and when a large structural change occurs, the transition occurs with heat and the luminous efficiency is lowered.
  • the phosphorescent compound is composed of a transition metal and a ligand.
  • a ligand for example, a biaryl type ligand in which an aromatic heterocycle and an aromatic ring (or an aromatic heterocycle) are connected by a single bond is often used, and the main cause of increasing non-radiative transition is biaryl.
  • the “biaryl type ligand” is not a compound in which two aromatic rings are connected by a single bond, but a compound in which an aromatic ring and an aromatic heterocyclic ring are connected by a single bond, It is a compound in which aromatic heterocycles are connected by a single bond, and these aromatic rings and / or aromatic heterocycles may further have a substituent.
  • the aromatic ring and aromatic heterocycle (or two aromatic heterocycles) constituting the biaryl-type ligand coordinated with the transition metal are single bonds. Since they are coupled, it is considered that structural change occurs and non-radiative transition increases.
  • the means for fixing the structure of the biaryl ligand is a means that can also suppress association and aggregation of dopants that cause concentration quenching and excimer emission.
  • the association / aggregation between the dopants may occur immediately after the film formation, but it occurs more prominently when electrolysis or local Joule heat is applied to the light-emitting layer thin film over time.
  • the association / aggregation of the dopants with the passage of time changes the state of the film in the light emitting layer, which changes the ease of hole flow and the ease of electron flow. It is necessary to suppress the value from changing and causing a voltage increase during driving.
  • the manufacturing method of the iridium complex used for an organic EL element it is common to make it react with a ligand using iridium chloride. In this reaction, hydrochloric acid is generated as a by-product. Therefore, when the ligand contains, for example, an imidazole ring, if H is present at the N-position of the imidazole, charge exchange occurs between H and Cl, such as formation of hydrochloride. Therefore, it is difficult to synthesize an Ir complex unless some substituent such as a methyl group is introduced at the N position.
  • the light emitting layer unit may have a non-light emitting intermediate layer between a plurality of light emitting layers, and may have a multi-photon unit configuration in which the intermediate layer is a charge generation layer.
  • the charge generating layer ITO (indium tin oxide), IZO (indium zinc oxide), ZnO 2, TiN, ZrN , HfN, TiOx, VOx, CuI, InN, GaN, CuAlO 2, CuGaO 2 , conductive inorganic compound layers such as SrCu 2 O 2 , LaB 6 , RuO 2 , double-layer films such as Au / Bi 2 O 3 , SnO 2 / Ag / SnO 2 , ZnO / Ag / ZnO, Bi 2 Multilayer films such as O 3 / Au / Bi 2 O 3 , TiO 2 / TiN / TiO 2 , TiO 2 / ZrN / TiO 2 , fullerenes such as C 60
  • 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 or the electron transport layer and the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.
  • the total thickness of the light emitting layer is not particularly limited, but from the viewpoint of improving the stability of the emission color against the drive current and the uniformity of the film, preventing unnecessary application of high voltage during light emission. It is preferably adjusted in the range of 2 nm to 5 ⁇ m, more preferably adjusted in the range of 2 to 200 nm, particularly preferably in the range of 5 to 100 nm.
  • the light emitting layer of the organic EL device of the present invention preferably contains a light emitting dopant (phosphorescent dopant, fluorescent light emitting dopant, etc.) compound and a host compound.
  • the luminescent dopant (a luminescent dopant, a dopant compound, and only a dopant) is demonstrated.
  • a fluorescent luminescent dopant also referred to as a fluorescent dopant, a fluorescent compound, or a fluorescent luminescent compound
  • a phosphorescent dopant also referred to as a phosphorescent dopant, a phosphorescent compound, a phosphorescent compound, or the like.
  • a phosphorescent dopant is a compound in which light emission from an excited triplet is observed, specifically a compound that emits phosphorescence at room temperature (25 ° C.), and a phosphorescence quantum yield. Is defined as a compound of 0.01 or more at 25 ° C., but a preferable phosphorescence quantum yield is 0.1 or more.
  • the phosphorescence quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of Experimental Chemistry Course 4 of the 4th edition. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence dopant according to the present invention achieves the phosphorescence quantum yield (0.01 or more) in any solvent. That's fine.
  • the phosphorescent dopant There are two types of light emission of the phosphorescent dopant in principle. One is the recombination of carriers on the host compound to which carriers are transported to generate the excited state of the luminescent host compound, and this energy is used as the phosphorescent dopant. It is an energy transfer type in which light emission from a phosphorescent dopant is obtained by moving to. The other is a carrier trap type in which a phosphorescent dopant becomes a carrier trap, and carrier recombination occurs on the phosphorescent dopant, and light emission from the phosphorescent dopant is obtained. In any case, it is a condition that the excited state energy of the phosphorescent dopant is lower than the excited state energy of the host compound.
  • the iridium complex of the present invention has a bidentate ligand containing an aromatic heterocyclic ring.
  • the bidentate ligand is a ligand in which the aromatic heterocycle and another aromatic heterocycle or an aromatic ring are bonded by a single bond, and has a hydrogen bond in the ligand.
  • the hydrogen bond is a non-covalent bond formed by a hydrogen atom covalently bonded to an atom having a large electronegativity with a lone electron pair of a nitrogen atom, an oxygen atom or a sulfur atom located at a predetermined distance and angle. It is an attractive interaction of sex.
  • an atom covalently bonded to a hydrogen atom forming a hydrogen bond can be expressed as X—H. Assume that hydrogen bonds are formed when the distance between them is in the range of 1.4 to 2.5 mm and the angle formed by XH... Y is in the range of 110 to 125 °.
  • the hydrogen bond formed in the ligand of the iridium complex of this invention is Gaussian98 (Gaussian98, Revision A.11.4, MJ Frisch, Software for molecular orbital calculation made by Gaussian, USA). et al, Gaussian, Inc., Pittsburgh PA, 2002.)
  • B3LYP / 6-31G * as a keyword as a keyword, the structure-optimized iridium complex is hydrogenated based on distance and angle. Judgment was made.
  • an atom hydrogen-bonded with the hydrogen atom forming the hydrogen bond is a nitrogen atom, an oxygen atom, a phosphorus atom, or a silicon atom because a strong hydrogen bond is formed.
  • the structure change can be suppressed by having a hydrogen bond in the ligand of the iridium complex, the site involved in light emission can be immobilized, and the non-radiative transition is suppressed. can do.
  • the iridium complex of the present invention preferably further has interligand hydrogen bonds, intermolecular hydrogen bonds, and other interactions.
  • the iridium complex of the present invention preferably has a partial structure represented by the following general formula (1).
  • a 1 and A 2 each represent an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a 3 represents an aromatic heterocyclic ring.
  • X 1 , X 5 , X 1a and X 5a each represent a nitrogen atom or a carbon atom.
  • X 2 to X 4 each represent a nitrogen atom, a carbon atom, an oxygen atom or a sulfur atom.
  • X 6 represents an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a silicon atom.
  • Ra represents a hydrogen atom, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkyl group or a cycloalkyl group.
  • n represents 0 or 1.
  • l represents 1 to 3.
  • m represents 0-2.
  • l + m 3.
  • the ring formed by X 1 to X 5 in the iridium complex is preferably an imidazole ring or a triazole ring.
  • a 1 in the iridium complex is preferably a benzene ring.
  • the iridium complex of this invention has the partial structure represented by following General formula (2).
  • a 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a 3 represents an aromatic heterocyclic ring containing X 1a and X 5a .
  • a 4 represents an aromatic heterocyclic ring containing X 6 .
  • X 1 , X 5 , X 1a and X 5a each represent a nitrogen atom or a carbon atom.
  • X 2 to X 4 represent a nitrogen atom, a carbon atom, an oxygen atom or a sulfur atom.
  • X 6 represents an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a silicon atom.
  • X 7 and X 8 represent CRc and N, and Rc represents a hydrogen atom or a substituent.
  • ns represents 0 or 1.
  • l represents 1 to 3.
  • m represents 0-2.
  • l + m 3.
  • the iridium complex of this invention has the partial structure represented by following General formula (3).
  • a 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a 3 represents an aromatic heterocyclic ring.
  • X 1 , X 5 , X 1a and X 5a each represent a nitrogen atom or a carbon atom.
  • X 2 to X 4 each represent a nitrogen atom, a carbon atom, an oxygen atom or a sulfur atom.
  • X 6 represents an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a silicon atom.
  • Ra represents a hydrogen atom, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkyl group or a cycloalkyl group.
  • R 1 represents an electron withdrawing group.
  • n 0 or 1.
  • l 1 to 3.
  • m 0-2.
  • l + m 3.
  • an alkoxycarbonyl group in addition to the electron withdrawing groups included in the structural formulas of the iridium complexes D-1 to D-38 shown in the following specific examples, an alkoxycarbonyl group, an aryloxycarbonyl group, a sulfamoyl group, an acyl group Amide groups, carbamoyl groups, sulfinyl groups, alkylsulfonyl groups, arylsulfonyl groups, heteroarylsulfonyl groups, cyano groups, nitro groups, and the like are also preferably used.
  • the iridium complex of this invention has the partial structure represented by following General formula (4).
  • a 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • a 3 represents an aromatic heterocyclic ring.
  • X 1 , X 5 , X 1a and X 5a each represent a nitrogen atom or a carbon atom.
  • X 2 to X 4 each represent a nitrogen atom, a carbon atom, an oxygen atom or a sulfur atom.
  • X 6 represents an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a silicon atom.
  • Ra represents a hydrogen atom, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkyl group or a cycloalkyl group.
  • R 2 represents an electron donating group.
  • n 0 or 1.
  • l 1 to 3.
  • m 0-2.
  • l + m 3.
  • an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkylthio group, Groups such as cycloalkylthio group, arylthio group, amino group, hydroxy group, mercapto group and silyl group are also preferably used.
  • the iridium complex of this invention has a structure represented by following General formula (5).
  • V represents a trivalent linking group. It is linked to L 1 , L 2 and L 3 by a covalent bond.
  • L 1 to L 3 are each a partial structure represented by the following general formula (6).
  • X 1 represents a nitrogen atom or a carbon atom.
  • X 2 to X 4 each represent a nitrogen atom, a carbon atom, an oxygen atom or a sulfur atom.
  • X 6 represents an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a silicon atom.
  • Ra represents a hydrogen atom, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a heterocyclic group, an alkyl group or a cycloalkyl group.
  • n represents 0 or 1. * Represents a binding site to V.
  • the partial structure represented by the general formulas (1) to (6) and the aromatic ring contained in the structure may further have a substituent, and the substituent is bonded to another group to form a condensed ring. It may be formed.
  • substituents include an alkyl group (for example, a methyl group, an ethyl group, a trifluoromethyl group, and an isopropyl group), an alkoxy group (for example, a methoxy group and an ethoxy group), and a halogen atom (for example, a fluorine atom).
  • Nitro group dialkylamino group (for example, dimethylamino group), trialkylsilyl group (for example, trimethylsilyl group), triarylsilyl group (for example, triphenylsilyl group), triheteroarylsilyl group (for example, triphenylsilyl group) Pyridylsilyl group etc.), benzyl group, aryl group (eg phenyl group etc.), heteroaryl group (eg pyridyl group, carbazolyl group etc.) and the like.
  • dialkylamino group for example, dimethylamino group
  • trialkylsilyl group for example, trimethylsilyl group
  • triarylsilyl group for example, triphenylsilyl group
  • triheteroarylsilyl group for example, triphenylsilyl group
  • the iridium complex of the present invention is Gaussian 03 (Gaussian 98, Revision C.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.), which is software for molecular orbital calculation manufactured by Gaussian, USA.
  • Gaussian 03 Gaussian 98, Revision C.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.
  • B3LYP / 6-31G * as a keyword, structural optimization is performed, and using this optimal structure, 6-311 ++ G (2df, 2p) is used as a keyword to perform one-point calculation, and the dissociation energy of the hydrogen atom is calculated. Asked.
  • the dissociation energy of a hydrogen atom that forms a hydrogen bond in the ligand of the iridium complex of the present invention is preferably 390 kJ / mol or less, more preferably 375 kJ / mol or less, and 360 kJ / mol or less. It is particularly preferred. Table 1 shows the calculated dissociation energy.
  • the dissociation energy of the hydrogen atom forming the hydrogen bond is 390 kJ / mol or less because the hydrogen bond can suppress the structural change of the ligand.
  • Fluorescent dopant examples include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, Examples include perylene dyes, stilbene dyes, polythiophene dyes, rare-earth complex phosphors, and compounds having high fluorescence quantum yields typified by laser dyes.
  • the light emitting dopant used in the present invention may be used in combination of a plurality of types of compounds, a combination of phosphorescent dopants having different structures, or a combination of a phosphorescent dopant and a fluorescent dopant.
  • the luminescent dopant a conventionally known luminescent dopant may be used in combination with the iridium complex of the present invention.
  • the compounds described in International Publication No. 2013/061850 can be preferably used, but the present invention is not limited thereto.
  • a host compound (also referred to as a light-emitting host or a light-emitting host compound) that can be used in the present invention has a mass ratio in the layer of 20% or more among the compounds contained in the light-emitting layer, and a room temperature ( 25 ° C.) is defined as a compound having a phosphorescence quantum yield of phosphorescence of less than 0.1.
  • the phosphorescence quantum yield is preferably less than 0.01.
  • the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.
  • the host compound that can be used in the present invention 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.
  • a conventionally well-known host compound may be used independently, and may be used in combination of multiple types. By using a plurality of types of host compounds, it is possible to adjust the movement of charges, and the organic EL element can be made highly efficient. Moreover, it becomes possible to mix different light emission by using multiple types of the iridium complex of this invention used as the said phosphorescence dopant, and / or a conventionally well-known compound, and, thereby, arbitrary luminescent colors can be obtained.
  • the host compound used in the present invention may be a low molecular compound, a high molecular compound having a repeating unit, or a low molecular compound (polymerizable host compound) having a polymerizable group such as a vinyl group or an epoxy group. Of course, one or more of such compounds may be used.
  • host compounds include compounds described in the following documents. JP-A-2001-257076, 2002-308855, 2001-313179, 2002-319491, 2001-357777, 2002-334786, 2002-8860, 2002-334787, 2002-15871, 2002-334788, 2002-43056, 2002-334789, 2002-75645, 2002-338579, 2002-105445 gazette, 2002-343568 gazette, 2002-141173 gazette, 2002-352957 gazette, 2002-203683 gazette, 2002-363227 gazette, 2002-231453 gazette, No. 003-3165, No. 2002-234888, No. 2003-27048, No. 2002-255934, No. 2002-260861, No. 2002-280183, No. 2002-299060, No. 2002. -302516, 2002-305083, 2002-305084, 2002-308837, and the like.
  • the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • the electron transport layer can be provided with a single layer or a plurality of layers.
  • the electron transport layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer.
  • any conventionally known compound may be selected and used in combination. Is possible.
  • electron transport materials examples include polycyclic aromatic hydrocarbons such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, Heterocyclic tetracarboxylic anhydride, carbodiimide, fluorenylidenemethane derivative, anthraquinodimethane and anthrone derivative, oxadiazole derivative, carboline derivative, or carbon atom of the hydrocarbon ring constituting the carboline ring of the carboline derivative Derivatives having a ring structure in which at least one is substituted with a nitrogen atom, hexaazatriphenylene derivatives, and the like can be mentioned.
  • polycyclic aromatic hydrocarbons such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, Heterocyclic tetrac
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron-withdrawing group can also be used as an electron transport material. It is also possible to use a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain.
  • metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the like, and the central metals of these metal complexes are In, Mg, Metal complexes replaced with Cu, Ca, Sn, Ga, or Pb can also be used as the electron transport material.
  • metal-free or metal phthalocyanine or those having a terminal substituted with an alkyl group or a sulfonic acid group can be used as the electron transport material.
  • An inorganic semiconductor such as n-type-Si and n-type-SiC can also be used as an electron transport material.
  • the electron transport layer is made of an electron transport material such as a vacuum deposition method, a wet method (also referred to as a wet process, such as a spin coating method, a casting method, a die coating method, a blade coating method, a roll coating method, an ink jet method, a printing method, or a spraying method.
  • the film is preferably formed by thinning by a coating method, curtain coating method, LB method (Langmuir Brodgett method, etc.).
  • the thickness of the electron transport layer is not particularly limited, but is usually about 5 to 5000 nm, preferably 5 to 200 nm.
  • the electron transport layer may have a single layer structure composed of one or more of the above materials.
  • an n-type dopant such as a metal compound such as a metal complex or a metal halide may be doped.
  • the compounds described in International Publication No. 2013/061850 can be preferably used. It is not limited to.
  • cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • the emission luminance is advantageously improved.
  • a transparent or semi-transparent cathode can be produced by producing a conductive transparent material, which will be described later in the description of the anode, after producing the above metal with a thickness of 1 to 20 nm on the cathode.
  • a transparent or semi-transparent cathode can be produced by producing a conductive transparent material, which will be described later in the description of the anode, after producing the above metal with a thickness of 1 to 20 nm on the cathode.
  • Injection layer electron injection layer (cathode buffer layer), hole injection layer >>
  • the injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. You may let them.
  • An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance. “Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • anode buffer layer hole injection layer
  • anode buffer layer hole injection layer
  • copper phthalocyanine is used.
  • Examples thereof include a buffer layer, a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) and polythiophene, and an orthometalated complex layer represented by tris (2-phenylpyridine) iridium complex.
  • a buffer layer a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) and polythiophene
  • an orthometalated complex layer represented by tris (2-phenylpyridine) iridium complex.
  • cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc.
  • Metal buffer layer typified by, alkali metal compound buffer layer typified by lithium fluoride and potassium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride and cesium fluoride, typified by aluminum oxide Examples thereof include an oxide buffer layer.
  • the buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m, although it depends on the material.
  • ⁇ Blocking layer hole blocking layer, electron blocking layer>
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film. For example, it is described in JP-A Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on November 30, 1998)” on page 237. There is a hole blocking (hole blocking) layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking. Moreover, the structure of the electron carrying layer mentioned above can be used as a hole-blocking layer as needed.
  • the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
  • the hole blocking layer includes a carbazole derivative, a carboline derivative, a diazacarbazole derivative (the diazacarbazole derivative is a nitrogen atom in which any one of carbon atoms constituting the carboline ring is cited as the host compound described above. It is preferable to contain the thing replaced by.
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.
  • the thickness of the hole blocking layer and the electron transporting layer according to the present invention is preferably 3 to 100 nm, and more preferably 5 to 30 nm.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has any of hole injection or transport and electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, particularly thiophene oligomers.
  • azatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as hole transport materials.
  • the above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminoph
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
  • JP-A-11-251067, J. Org. Huang et. al. A so-called p-type hole transport material as described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used. In the present invention, these materials are preferably used because a light-emitting element with higher efficiency can be obtained.
  • the hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can.
  • the layer thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 to 200 nm.
  • This hole transport layer may have a single layer structure composed of one or more of the above materials.
  • a hole transport layer having a high p property doped with impurities can be used.
  • examples thereof include JP-A-4-297076, JP-A-2000-196140, JP-A-2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
  • an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • an electrode substance include metals such as Au, and conductive transparent materials such as CuI, 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.
  • a thin film may be formed by vapor deposition or sputtering of these electrode materials, and a pattern of a desired shape may be formed by photolithography, or when pattern accuracy is not required (about 100 ⁇ m or more) A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • a wet film forming method such as a printing method or a coating method can also be used.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
  • 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 (TAC), cellulose acetate butyrate, cellulose acetate propionate ( CAP), cellulose esters such as cellulose acetate phthalate, cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones Cycloolefin resins such as polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylates, 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. , And a relative humidity (90 ⁇ 2)%) of 0.01 g / m 2 ⁇ 24 h or less is preferable, and the oxygen permeability measured by a method according to JIS K 7126-1987 is also preferable. It is preferably a high-barrier film having 1 ⁇ 10 ⁇ 3 ml / m 2 ⁇ 24 h ⁇ atm or less and a water vapor permeability of 1 ⁇ 10 ⁇ 5 g / m 2 ⁇ 24 h or less.
  • the material for forming the barrier layer may be any material as long as it 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 layer is not particularly limited.
  • a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or 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 include metal plates such as aluminum and stainless steel, films, opaque resin substrates, and ceramic substrates.
  • the external extraction yield at room temperature for light emission of the organic EL device of the present invention is preferably 1% or more, and more preferably 5% or more.
  • the external extraction quantum yield (%) 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.
  • a device comprising an anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer (electron injection layer) / cathode Will be described.
  • a desired electrode material for example, a thin film made of an anode material is formed on a suitable substrate so as to have a thickness of 1 ⁇ m or less, preferably 10 to 200 nm, to produce an anode.
  • a thin film containing an organic compound such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, or a cathode buffer layer, which is an element material, is formed thereon.
  • a thin film can be formed by a vacuum deposition method, a wet method (also referred to as a wet process), or the like.
  • Wet methods include spin coating, casting, die coating, blade coating, roll coating, ink jet, printing, spray coating, curtain coating, and LB, but precise thin films can be formed.
  • a method having a high suitability for a roll-to-roll method such as a die coating method, a roll coating method, an ink jet method, or a spray coating method is preferable. Different film formation methods may be applied for each layer.
  • liquid medium for dissolving or dispersing the organic EL material such as a luminescent dopant used in the present invention include, for example, ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, 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 dimethylformamide (DMF) and DMSO can be used.
  • a dispersion method it can disperse
  • a thin film made of a cathode material is formed thereon so as to have a thickness of 1 ⁇ m or less, preferably in the range of 50 to 200 nm, and a desired organic EL device can be obtained by providing a cathode.
  • the order can be reversed, and the cathode, cathode buffer layer, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, and anode can be formed in this order.
  • the organic EL device of the present invention is preferably produced from the hole injection layer to the cathode consistently by a single evacuation, but it may be taken out halfway and subjected to different film forming methods. At that time, it is preferable to perform the work in a dry inert gas atmosphere.
  • 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 those formed from polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like.
  • Examples of the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
  • a polymer film and a metal film can be preferably used because the element can be thinned.
  • the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 ⁇ 10 ⁇ 3 ml / m 2 ⁇ 24 h ⁇ atm or less, and measured by a method according to JIS K 7129-1992.
  • the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)%) is preferably 1 ⁇ 10 ⁇ 3 g / m 2 ⁇ 24 h or less.
  • the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant may be dispersed in the adhesive.
  • 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.
  • a material for forming the film any material may be used as long as it has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
  • vacuum deposition 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 is also possible.
  • a hygroscopic compound can also be enclosed inside. Examples of the hygroscopic compound include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
  • metal halides eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.
  • perchloric acids eg perchloric acid Barium, magnesium perchlorate, and the like
  • anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
  • a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the support substrate with the organic layer interposed therebetween or the sealing film.
  • the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, etc. used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
  • the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15 to 20% of the light generated in the light emitting layer. Is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light is totally reflected between the light and the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the direction of the element side surface.
  • a method 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
  • 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 one of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • by combining these means it is possible to obtain an element having higher brightness or durability.
  • the low refractive index layer include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less. Further, 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 or second-order diffraction.
  • Light that cannot be emitted due to total internal reflection, etc. is diffracted by introducing a diffraction grating in any layer or medium (in the transparent substrate or transparent electrode), and the light is emitted outside. I want to take it out.
  • the introduced diffraction grating desirably 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 one of the layers or in the medium (in the transparent substrate or the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.
  • the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction grating is preferably two-dimensionally repeated such as a square lattice, a triangular lattice, or a honeycomb lattice.
  • the organic EL device of the present invention is processed on the light extraction side of the substrate, for example, so as to provide a microlens array-like structure, or in combination with a so-called condensing sheet, for example, with respect to a specific direction, for example, the device light emitting surface.
  • a specific direction for example, the device light emitting surface.
  • the luminance in a specific direction can be increased.
  • the microlens array quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably 10 to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
  • the condensing sheet for example, a sheet that is put into practical use in an LED backlight of a liquid crystal display device can be used.
  • a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • the shape of the prism sheet for example, the base material may be formed by forming a ⁇ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.
  • a light diffusing plate and a film with a condensing sheet for example, a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
  • the organic EL element of the present invention can be used as an electronic device, a display device, a display, and various light emitting devices.
  • light emitting devices include lighting devices (home lighting, interior lighting), clocks and backlights for liquid crystals, billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light Although the light source of a sensor etc. are mentioned, It is not limited to this, Especially, it can use effectively for the use as a backlight of a liquid crystal display device, and a light source for illumination.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like during film formation, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned.
  • a conventionally known method is used. Can do.
  • the light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 7.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with a total of CS-1000 (manufactured by Konica Minolta Co., Ltd.) is applied to the CIE chromaticity coordinates.
  • CS-1000 manufactured by Konica Minolta Co., Ltd.
  • the display device of the present invention comprises the organic EL element of the present invention.
  • the display device of the present invention may be single color or multicolor, the multicolor display device will be described here.
  • a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by vapor deposition, casting, spin coating, ink jet, printing, or the like.
  • the method is not limited. However, the vapor deposition method, the ink jet method, the spin coating method, and the printing method are preferable.
  • the configuration of the organic EL element provided in the display device is selected from the above-described configuration examples of the organic EL element as necessary.
  • the manufacturing method of an organic EL element is as having shown to the one aspect
  • the multicolor display device can be used as a display device, a display, and various light emission sources.
  • a display device or display full-color display is possible by using three types of organic EL elements of blue, red, and green light emission.
  • the display device and display include a television, a personal computer, a mobile device, an AV device, a character broadcast display, and an information display in an automobile.
  • the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.
  • Light sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sources for optical sensors, etc.
  • the present invention is not limited to these examples.
  • FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements. It is a schematic diagram of a display such as a mobile phone that displays image information by light emission of an organic EL element.
  • the display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, a wiring unit C that electrically connects the display unit A and the control unit B, and the like.
  • the control unit B is electrically connected to the display unit A via the wiring unit C, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside. Sequentially emit light according to the image data signal, scan the image, and display the image information on the display unit A.
  • FIG. 2 is a schematic diagram of a display device using an active matrix method.
  • the display unit A includes a wiring unit C including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate.
  • the main members of the display unit A will be described below.
  • FIG. 2 shows a case where the light emitted from the pixel 3 (the emitted light L) is extracted in the white arrow direction (downward).
  • the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at the orthogonal positions (details are illustrated Not)
  • the pixel 3 receives an image data signal from the data line 6 and emits light according to the received image data.
  • Full-color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
  • FIG. 3 is a schematic diagram showing a pixel circuit.
  • the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
  • a full color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 in a plurality of pixels, and juxtaposing them on the same substrate.
  • an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
  • a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5
  • the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is supplied to the capacitor 13 and the driving transistor 12. Is transmitted to the gate.
  • the capacitor 13 is charged according to the potential of the image data signal, and the drive transistor 12 is turned on.
  • the drive transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10, and the power supply line 7 connects to the organic EL element 10 according to the potential of the image data signal applied to the gate. Current is supplied.
  • the driving of the switching transistor 11 is turned off.
  • the driving of the driving transistor 12 is kept on and the next scanning signal is applied. Until then, the light emission of the organic EL element 10 continues.
  • the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
  • the organic EL element 10 emits light by the switching transistor 11 and the drive transistor 12 that are active elements for the organic EL element 10 of each of the plurality of pixels, and the light emission of the organic EL element 10 of each of the plurality of pixels 3. It is carried out.
  • Such a light emitting method is called an active matrix method.
  • the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or by turning on / off a predetermined light emission amount by a binary image data signal. Good.
  • the potential of the capacitor 13 may be held continuously until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
  • a passive matrix light emission drive in which the organic EL element emits light according to the data signal only when the scanning signal is scanned.
  • FIG. 4 is a schematic view of a passive matrix display device.
  • a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
  • the scanning signal of the scanning line 5 is applied by sequential scanning, the pixels 3 connected to the applied scanning line 5 emit light according to the image data signal.
  • the pixel 3 has no active element, and the manufacturing cost can be reduced.
  • the organic EL element of the present invention By using the organic EL element of the present invention, a display device with improved luminous efficiency was obtained.
  • the organic EL element of the present invention can also be used for a lighting device.
  • the organic EL element of the present invention may be used as an organic EL element having a resonator structure.
  • Examples of the purpose of use of the organic EL element having such a resonator structure include a light source of an optical storage medium, a light source of an electrophotographic copying machine, a light source of an optical communication processing machine, and a light source of an optical sensor. It is not limited. Moreover, you may use for the said use by making a laser oscillation.
  • the organic EL element of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a type for directly viewing a still image or a moving image. It may be used as a display device (display).
  • the driving method when used as a display device for reproducing a moving image may be either a passive matrix method or an active matrix method.
  • a full-color display device can be manufactured by using two or more organic EL elements of the present invention having different emission colors.
  • the luminescent compound of the present invention can be applied to an organic EL element that emits substantially white light as a lighting device.
  • white light emission can be obtained by simultaneously emitting a plurality of light emission colors and mixing the colors.
  • the light emission may include three light emission maximum wavelengths of three primary colors of red, green and blue, or two light emission utilizing a complementary color relationship such as blue and yellow, blue green and orange, etc. It may contain a maximum wavelength.
  • the method for forming the organic EL device of the present invention may be simply arranged by providing a mask only when forming a light emitting layer, a hole transport layer, an electron transport layer, or the like, and separately coating with the mask. Since the other layers are common, patterning of a mask or the like is unnecessary, and for example, an electrode film can be formed on one surface by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, or the like, and productivity is improved. According to this method, unlike a white organic EL device in which light emitting elements of a plurality of colors are arranged in parallel in an array, the elements themselves are luminescent white.
  • FIG. 1 One Embodiment of Lighting Device of the Present Invention.
  • the non-light emitting surface of the organic EL device of the present invention is covered with a glass case, a 300 ⁇ m thick glass substrate is used as a sealing substrate, and an epoxy photocurable adhesive (LUX The track LC0629B) is applied, and this is overlaid on the cathode and brought into close contact with the transparent support substrate, irradiated with UV light from the glass substrate side, cured, sealed, and illuminated as shown in FIGS.
  • a device can be formed.
  • FIG. 1 An epoxy photocurable adhesive
  • FIG. 5 shows a schematic diagram of the lighting device, and the organic EL element of the present invention (organic EL element 101 in the lighting device) is covered with a glass cover 102 (note that the sealing operation with the glass cover is performed by lighting. This was performed in a glove box under a nitrogen atmosphere (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more) without bringing the organic EL element 101 in the apparatus into contact with the air.
  • FIG. 6 is a cross-sectional view of the lighting device.
  • reference numeral 105 denotes a cathode
  • 106 denotes an organic layer
  • 107 denotes a glass substrate with a transparent electrode.
  • the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum deposition apparatus, while ⁇ -NPD (N, N′-Diphenyl-N, N′-bis (1-naphthalenyl) -1,1 is attached to a resistance heating boat made of molybdenum.
  • the hole-transporting layer was heated by energizing the heating boat containing the host compound OC-4 and the heating boat containing the comparative compound 1 at a deposition rate of 0.1 nm / second and 0.010 nm / second, respectively.
  • a 40 nm light-emitting layer was provided by co-evaporation.
  • the heating boat containing BCP was energized and heated, and was deposited on the hole blocking layer at a deposition rate of 0.1 nm / second to provide an electron transport layer of 30 nm. Subsequently, lithium fluoride 0.5 nm was deposited as a cathode buffer layer, and aluminum 110 nm was further deposited to form a cathode, thereby fabricating an organic EL device 1-1.
  • the external quantum efficiency (EQE) can be expressed by the product of the internal quantum efficiency (IQE) and the light extraction efficiency (OC) (see formula (A)).
  • Formula (A): EQE IQE ⁇ OC
  • EQE and OC obtained by measurement and analysis are applied to the formula (A) to calculate the internal quantum efficiency of the light emitting material of the organic EL element 1-1.
  • the internal quantum efficiency was calculated in the same manner for the organic EL elements 1-2 to 1-20.
  • Table 2 shows relative values when the internal quantum efficiency of the organic EL element 1-1 is 100.
  • Table 2 shows that the organic EL element using the iridium complex of the present invention has higher internal quantum efficiency (luminous efficiency) than the organic EL element of the comparative example.
  • the organic EL element was measured for the resistance value of the light emitting layer before and after driving for 1000 hours under room temperature (25 ° C.) and constant current conditions of 2.5 mA / cm 2 , and the calculation results are shown below.
  • the change rate of the resistance value was obtained by calculation.
  • Table 2 shows the relative ratio when the rate of change of the resistance value of the organic EL element 1-1 is 100.
  • Change rate of resistance value before and after driving
  • a value closer to 0 indicates a smaller rate of change before and after driving. From Table 2, it was found that the organic EL device using the iridium complex of the present invention had a smaller change rate of the resistance value of the light emitting layer than the organic EL device of the comparative example, and had an excellent emission lifetime.
  • the iridium complex of the present invention can be suitably used in the field of organic EL elements, and further, display devices, displays, home lighting, interior lighting, clocks and liquid crystal backlights equipped with organic EL elements.
  • Wide light-emitting sources such as signboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light sources of optical sensors, and general household appliances that require display devices can be suitably used.

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

Abstract

　La présente invention vise à fournir un complexe d'iridium ayant une efficacité d'émission de lumière et une durabilité améliorées, un matériau électroluminescent organique et un élément électroluminescent organique qui utilisent le complexe d'iridium, un dispositif d'éclairage et un dispositif d'affichage dotés de l'élément électroluminescent organique. Ce complexe d'iridium présente un ligand bidenté comprenant un noyau hétéroaromatique et est caractérisé en ce que le ligand bidenté est un ligand dans lequel le noyau hétéroaromatique et un autre noyau hétéroaromatique ou un cycle aromatique sont liés par une liaison simple, et le ligand a une liaison hydrogène à l'intérieur de ce dernier.
PCT/JP2015/078371 2014-10-07 2015-10-06 Complexe d'iridium, matériau électroluminescent organique, élément électroluminescent organique, dispositif d'affichage et dispositif d'éclairage WO2016056562A1 (fr)

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US10720587B2 (en) 2016-07-19 2020-07-21 Universal Display Corporation Organic electroluminescent materials and devices
US11370809B2 (en) 2019-02-08 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
US11912724B2 (en) 2021-02-05 2024-02-27 Samsung Electronics Co., Ltd. Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device
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US10720587B2 (en) 2016-07-19 2020-07-21 Universal Display Corporation Organic electroluminescent materials and devices
CN109280064A (zh) * 2017-07-20 2019-01-29 三星电子株式会社 有机金属化合物和包括其的有机发光器件
US11370809B2 (en) 2019-02-08 2022-06-28 Universal Display Corporation Organic electroluminescent materials and devices
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US11912724B2 (en) 2021-02-05 2024-02-27 Samsung Electronics Co., Ltd. Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

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