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WO2013114966A1 - Composé complexe d'iridium, matériau pour élément électroluminescent organique, élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage - Google Patents

Composé complexe d'iridium, matériau pour élément électroluminescent organique, élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage Download PDF

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WO2013114966A1
WO2013114966A1 PCT/JP2013/050892 JP2013050892W WO2013114966A1 WO 2013114966 A1 WO2013114966 A1 WO 2013114966A1 JP 2013050892 W JP2013050892 W JP 2013050892W WO 2013114966 A1 WO2013114966 A1 WO 2013114966A1
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organic
hydrocarbon ring
aromatic hydrocarbon
aromatic
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大津　信也
大野　香織
加藤　栄作
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Konica Minolta Inc
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Definitions

  • the present invention relates to an iridium complex compound, an organic electroluminescence element material, an organic electroluminescence element, an illumination device, and a display device.
  • 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 a positive electrode injected from the anode by applying an electric field.
  • This is a light emitting device that uses the emission of light (fluorescence / phosphorescence) when excitons are generated by recombining electrons injected from holes and cathodes in the light emitting layer to generate excitons. is there.
  • An organic EL element is an all-solid-state element composed of an organic material film with a thickness of only a submicron between electrodes, and can emit light at a voltage of several volts to several tens of volts. It is expected to be used for next-generation flat display and lighting.
  • Non-Patent Document 1 As for development of organic EL elements for practical use, Princeton University has reported organic EL elements that use phosphorescence emission from excited triplets (see, for example, Non-Patent Document 1), and since then phosphorescence at room temperature. Research on materials exhibiting the above has become active (see, for example, Patent Document 1 and Non-Patent Document 2).
  • 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 previous 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 (see Non-Patent Document 3, for example).
  • the phosphorescence emission method is a method having a very high potential.
  • an organic EL device using phosphorescence emission is greatly different from an organic EL device using fluorescence emission, and controls the position of the emission center.
  • the method particularly how to recombine within the light emitting layer and how to stably emit light, is an important technical issue in capturing the efficiency and lifetime of the device.
  • a multi-layered element having a hole transport layer located on the anode side of the light emitting layer and an electron transport layer located on the cathode side of the light emitting layer in a form adjacent to the light emitting layer is well known.
  • a mixed layer using a host compound and a phosphorescent compound as a dopant is often used for the light emitting layer.
  • FIrpic is known as a typical blue phosphorescent compound, and a short wave is realized by substituting fluorine for the main ligand phenylpyridine and using picolinic acid as a secondary ligand. Yes.
  • These dopants have achieved high-efficiency devices by combining carbazole derivatives and triarylsilanes as host compounds. However, since the light emission lifetime of the devices is greatly deteriorated, improvement of the trade-off has been demanded. .
  • Patent Document 3 metal complexes having specific ligands are disclosed in Patent Document 3 and Patent Document 4 as blue phosphorescent compounds having high potential.
  • the stability of an organic EL device is improved by using a specific host compound in combination with a blue phosphorescent compound having a 2-phenylimidazole ligand having a twisted aryl component with extended conjugation. It is described that high luminous efficiency and low driving voltage can be realized.
  • a bulky substituent such as a branched alkyl group at the ortho position of the twisted aryl component bonded to the imidazole ring, the steric effect inhibits packing between molecules, and there are few decomposition products at a lower temperature. It has been described that sublimation of can now be performed.
  • the doping concentration of the phosphorescent light emitting material in the light emitting layer changes from several% to several tens%, the light emission efficiency and the light emission lifetime of the element change.
  • the dope concentration is low, the carrier transportability and recombination probability are lowered, and the drive voltage and the light emission efficiency are liable to be lowered. Therefore, the carrier transportability needs to be improved.
  • the doping concentration is high, the light emitting material is likely to aggregate, resulting in triplet-triplet annihilation (TT annihilation) and generation of trap sites with low energy levels.
  • TT annihilation triplet-triplet annihilation
  • the emission lifetime is reduced.
  • the blue phosphorescent light emitting material since the blue phosphorescent light emitting material has a high T 1 , it is easily affected by external factors such as trap sites, and the aggregation between the light emitting materials is suppressed and uniform regardless of the concentration adjustment. It is important to disperse.
  • a material having a large dependence on the doping concentration with respect to the performance of these elements is preferable because it has a low production suitability because a slight change in the doping concentration during production affects the performance of the device. I can't say that.
  • the carrier transportability in the light emitting layer is also lowered, and as a result, the light emitting life of the device tends to be reduced.
  • the luminous efficiency and lifetime of the organic EL element are improved, but the thermal stability and sublimation property of the metal complex that is the organic EL element material.
  • the decomposition lifetime is generated when an organic layer is formed by vapor deposition using the metal complex, so that the light emission lifetime of the device may be reduced.
  • the white light-emitting organic EL device using a plurality of light-emitting materials has problems such as the chromaticity stability during continuous driving and the dependency of the doping concentration on the device performance, and the relationship between the dispersibility of the light-emitting materials and the lifetime. It has not been done.
  • an object of the present invention is to improve the thermal stability and sublimation property of an organometallic complex as an organic electroluminescence element material, thereby providing an organic electroluminescence element having a high luminous efficiency and a long lifetime, and an illumination device using the element And providing a display device.
  • a further object of the present invention is to eliminate the problem of chromaticity stability (chromaticity shift) during continuous driving in a white light-emitting organic electroluminescence device, and to improve the dope concentration dependency in device performance.
  • Another object of the present invention is to provide a long-life organic electroluminescence device by providing an iridium complex compound having high dispersibility.
  • An iridium complex compound represented by the following general formula (5 ′) is provided.
  • ring An, ring Bm and ring Bn each independently represent a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle.
  • R 1 m, R 2 m, R 1 n and R 2 n 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, Rc and Ra 3 are each independently hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl.
  • na and nc represent 1 or 2
  • nb represents an integer of 1 to 4
  • nR3 represents an integer of 1 to 4.
  • X represents O, S, SiRz1Rz2, NRz1 or CRz1Rz2, and Rz1 and Rz2 each independently represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n 3. Note that the structures of the three ligands coordinated to Ir are not all the same. ]
  • An iridium complex compound represented by the following general formula (5) is provided.
  • R 1 m, R 2 m, R 1 n and R 2 n are each independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, It represents a non-aromatic 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, 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, It represents a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • na and nc represent 1 or 2
  • nR3 represents an integer of 1 to 4.
  • X represents O, S, SiRz1Rz2, NRz1 or CRz1Rz2, and Rz1 and Rz2 each independently represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n 3.
  • An electroluminescence element material represented by the following general formula (5 ′) is provided.
  • ring An, ring Bm and ring Bn each independently represent a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle.
  • R 1 m, R 2 m, R 1 n and R 2 n 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, Rc and Ra 3 are each independently hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl.
  • na and nc represent 1 or 2
  • nb represents an integer of 1 to 4
  • nR3 represents an integer of 1 to 4.
  • X represents O, S, SiRz1Rz2, NRz1 or CRz1Rz2, and Rz1 and Rz2 each independently represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n 3. Note that the structures of the three ligands coordinated to Ir are not all the same. ]
  • An organic electroluminescence element material represented by the following general formula (5) is provided.
  • R 1 m, R 2 m, R 1 n and R 2 n are each independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, It represents a non-aromatic 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, 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, It represents a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • na and nc represent 1 or 2
  • nR3 represents an integer of 1 to 4.
  • X represents O, S, SiRz1Rz2, NRz1 or CRz1Rz2, and Rz1 and Rz2 each independently represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n 3.
  • an organic electroluminescence device in which at least one organic layer including a light emitting layer is sandwiched between an anode and a cathode
  • An organic electroluminescence device characterized in that an iridium complex compound represented by the following general formula (5 ′) is contained in at least one of the organic layers.
  • ring An, ring Bm and ring Bn each independently represent a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle.
  • R 1 m, R 2 m, R 1 n and R 2 n 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, Rc and Ra 3 are each independently hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group, heteroaryl.
  • na and nc represent 1 or 2
  • nb represents an integer of 1 to 4
  • nR3 represents an integer of 1 to 4.
  • X represents O, S, SiRz1Rz2, NRz1 or CRz1Rz2, and Rz1 and Rz2 each independently represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n 3. Note that the structures of the three ligands coordinated to Ir are not all the same. ]
  • an organic electroluminescence device in which at least one organic layer including a light emitting layer is sandwiched between an anode and a cathode
  • An organic electroluminescence device characterized in that an iridium complex compound represented by the following general formula (5) is contained in at least one of the organic layers.
  • R 1 m, R 2 m, R 1 n and R 2 n are each independently an alkyl group having 2 or more carbon atoms, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, It represents a non-aromatic 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, 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, It represents a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • na and nc represent 1 or 2
  • nR3 represents an integer of 1 to 4.
  • X represents O, S, SiRz1Rz2, NRz1 or CRz1Rz2, and Rz1 and Rz2 each independently represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic group. Represents a heterocyclic group.
  • m represents 1 or 2
  • n represents 1 or 2
  • m + n 3.
  • a lighting device comprising the organic electroluminescence element.
  • a display device comprising the organic electroluminescence element is provided.
  • an organometallic complex as an organic electroluminescence device material having excellent thermal stability and sublimation properties, and by using this, an organic electroluminescence device having high emission efficiency and a long lifetime, An illumination device and a display device using the element can be provided.
  • the compound of the present invention has high carrier transportability and dispersibility, and as a result, a longer life can be achieved by improving the carrier balance.
  • an organic electroluminescence element having a small chromaticity shift at the time of continuous driving in a white light emitting organic EL element using a plurality of light emitting materials and having a small dependence on the doping concentration of the light emitting material, and an illumination device and a display device using the element Can be provided.
  • FIG. 4 is a schematic diagram of a display unit A.
  • FIG. It is a schematic diagram of a pixel. It is a schematic diagram of a passive matrix type full-color display device. It is the schematic of an illuminating device. It is a schematic diagram of an illuminating device.
  • the schematic block diagram of an organic electroluminescent full color display apparatus is shown.
  • the schematic block diagram of an organic electroluminescent full color display apparatus is shown.
  • the schematic block diagram of an organic electroluminescent full color display apparatus is shown.
  • the schematic block diagram of an organic electroluminescent full color display apparatus is shown.
  • the schematic block diagram of an organic electroluminescent full color display apparatus is shown.
  • the schematic block diagram of an organic electroluminescent full color display apparatus is shown.
  • the schematic block diagram of an organic electroluminescent full color display apparatus is shown.
  • the schematic block diagram of an organic electroluminescent full color display apparatus is shown.
  • 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 generation layer includes ITO (indium tin oxide), IZO (indium zinc oxide), ZnO 2 , TiN, ZrN, HfN, TiO x , VO x , CuI, InN, GaN, CuAlO 2.
  • the light emitting layer in the organic EL element of the present invention is preferably a white light emitting layer, and an illumination device using these is preferable.
  • 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 also be the interface between the light emitting layer and the adjacent layer.
  • the total thickness of the light emitting layer is not particularly limited, from the viewpoint of improving the stability of the emitted color against the uniformity of the film, preventing unnecessary application of high voltage during light emission, and driving current. It is preferably adjusted to a range of 2 to 5000 nm, more preferably adjusted to a range of 2 to 200 nm, and particularly preferably adjusted to a range of 5 to 100 nm.
  • a light-emitting dopant or a host compound which will be described later, is used. And the like can be formed by a method, an inkjet method, a printing method, a spray coating method, a curtain coating method, an LB method (Langmuir Brodgett method, etc.).
  • a hexadentate ortho metal iridium complex based on this invention it is preferable to form into a film by a wet process.
  • the light emitting layer of the organic EL device of the present invention contains a light emitting dopant (phosphorescent dopant (also referred to as phosphorescent dopant, phosphorescent dopant group) or fluorescent dopant) compound and a light emitting host compound. Is preferred.
  • a light emitting dopant phosphorescent dopant (also referred to as phosphorescent dopant, phosphorescent dopant group) or fluorescent dopant) compound and a light emitting host compound. Is preferred.
  • Luminescent dopant compound The luminescent dopant compound (a luminescent dopant, a dopant compound, and also only a dopant) is demonstrated.
  • a fluorescent dopant also referred to as a fluorescent compound
  • a phosphorescent dopant also referred to as a phosphorescent emitter, a phosphorescent compound, a phosphorescent compound, or the like
  • a fluorescent dopant also referred to as a fluorescent compound
  • a phosphorescent dopant also referred to as a phosphorescent emitter, a phosphorescent compound, a phosphorescent compound, or the like
  • the phosphorescent dopant according to the present invention 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 has a phosphorescence quantum yield of 25. Although it is defined as a compound of 0.01 or more at ° C., a preferable phosphorescence quantum yield is 0.1 or more.
  • the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7. 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. It ’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 an 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 serves as a carrier trap, carrier recombination occurs on the phosphorescent dopant, and light emission from the phosphorescent dopant compound 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 present inventors contain an iridium complex dopant represented by the following general formula (5 ′) in the organic layer of the organic EL element. It was clarified that the thermal stability and sublimation property of the organic EL element can be improved. That is, any one of the plurality of ligands coordinated to the iridium atom is made different from each other, and R 1 m, R 2 m, R 1 n and R 2 n in the general formula (5 ′) are carbon atoms.
  • the interaction between the iridium complexes was relaxed to improve the sublimation property, and further the thermal stability of the iridium complex was improved.
  • the iridium complex dopant is formed into a film by vapor deposition and an organic layer was formed, continuous repetition vapor deposition became possible.
  • the present inventors have found that the iridium complex dopant is contained in the organic EL element, thereby achieving high emission luminance and longer emission lifetime of the organic EL element.
  • the organic EL element of the present invention is constituted by containing an iridium complex compound represented by the following general formula (5 ′) as an organic EL element material in at least one of the organic layers.
  • an iridium complex compound represented by the following general formula (5 ′) is contained as an organic EL element material in the light emitting layer of the organic layer.
  • Iridium Complex Compound Represented by General Formula (5 ′) The iridium complex compound contained as the organic EL element material in the organic EL element of the present invention will be described.
  • the iridium complex compound according to the present invention is represented by the following general formula (5 ′).
  • each of ring An, ring Bn, and ring Bm independently represents a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle.
  • examples of the 5-membered or 6-membered aromatic hydrocarbon ring represented by the ring An, the ring Bn, and the ring Bm include a benzene ring.
  • examples of the 5-membered or 6-membered aromatic heterocycle represented by ring An, ring Bn and ring Bm include a furan ring, a thiophene ring, an oxazole ring, a pyrrole ring, a pyridine ring, Examples include pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, oxadiazole ring, triazole ring, imidazole ring, pyrazole ring, thiazole ring and the like.
  • at least one of the rings Bn and Bm is a benzene ring, more preferably the ring An is a benzene ring.
  • R 1 m and R 2 m 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.
  • examples of the alkyl group represented by R 1 m and R 2 m include an ethyl group, isopropyl group, n-butyl group, t-butyl group, n-hexyl group, 2-methyl group, Examples thereof include a hexyl group, a pentyl group, an adamantyl group, an n-decyl group, and an n-dodecyl group.
  • examples of the aromatic hydrocarbon ring group represented by R 1 m or R 2 m include a benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, and pyrene ring.
  • examples of the aromatic heterocyclic group represented by R 1 m or R 2 m include a silole ring, a furan ring, a thiophene ring, an oxazole ring, a pyrrole ring, a pyridine ring, a 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
  • examples of the non-aromatic hydrocarbon ring group represented by R 1 m or R 2 m include a cycloalkane (for example, a cyclopentane ring, a cyclohexane ring, etc.), a cycloalkoxy group (for example, , Cyclopentyloxy group, cyclohexyloxy group, etc.), cycloalkylthio group (eg, cyclopentylthio group, cyclohexylthio group, etc.), cyclohexylaminosulfonyl group, tetrahydronaphthalene ring, 9,10-dihydroanthracene ring, biphenylene ring, etc. And monovalent groups.
  • a cycloalkane for example, a cyclopentane ring, a cyclohexane ring, etc.
  • a cycloalkoxy group for example, , Cyclopenty
  • examples of the non-aromatic heterocyclic group represented by R 1 m or R 2 m include an epoxy ring, an aziridine ring, a thiirane ring, an oxetane ring, an azetidine ring, a thietane ring, and a tetrahydrofuran ring.
  • these groups represented by R 1 m or R 2 m may have a substituent, and the substituents may be bonded to each other to form a ring. good.
  • both R 1 m and R 2 m are an alkyl group or a cycloalkyl group having 2 or more carbon atoms, and one of R 1 m and R 2 m is A branched alkyl group having 3 or more carbon atoms is also preferred. More preferably, R 1 m and R 2 m are both branched alkyl groups having 3 or more carbon atoms.
  • R 1 n and R 2 n have the same meanings as R 1 m and R 2 m in general formula (5 ′).
  • Ra, Rb, 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, aryl. It represents an alkyl group, an aryl group, a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group, and may further have a substituent.
  • the aryl group and heteroaryl group represented by Ra, Rb, Rc, and Ra 3 include the aromatic hydrocarbon ring group represented by the above R 1 m or R 2 m and the aromatic group. Group heterocyclic group.
  • the non-aromatic hydrocarbon ring group and the non-aromatic heterocyclic group represented by Ra, Rb, Rc and Ra 3 are represented by the above-mentioned R 1 m or R 2 m.
  • Non-aromatic hydrocarbon ring group and non-aromatic heterocyclic group are mentioned.
  • na and nc represent 1 or 2
  • nb represents an integer of 1 to 4
  • nR3 represents an integer of 1 to 4.
  • X represents O, S, SiRz1Rz2, NRz1 or CRz1Rz2, and Rz1 and Rz2 each independently represents an alkyl group, an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic group Represents an aromatic hydrocarbon ring group or a non-aromatic heterocyclic group.
  • the aromatic hydrocarbon ring group, aromatic heterocyclic group, non-aromatic hydrocarbon ring group or non-aromatic heterocyclic group represented by Rz1 or Rz2 is represented by the above-mentioned R 1 m or R 2 m.
  • An aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic hydrocarbon ring group may be mentioned.
  • Iridium Complex Compound Represented by General Formula (5) The iridium complex compound represented by the above general formula (5 ′) is preferably represented by the following general formula (5).
  • R 1 m, R 2 m, R 1 n, R 2 n, Ra, Rc, Ra 3 , na, nc, nR 3, X, m, and n are the same as those in the general formula (5 ′).
  • R 1 m, R 2 m, R 1 n, R 2 n, Ra, Rc, Ra 3, na, is nc, nR3, X, same meaning as m and n.
  • Fluorescent dopant also called fluorescent compound
  • fluorescent dopants coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes , Polythiophene dyes, rare earth complex phosphors, and the like, and compounds having a high fluorescence quantum yield such as laser dyes.
  • the light-emitting dopant according to the present invention may be used in combination with a plurality of types of compounds, a combination of phosphorescent dopants having different structures, a phosphorescent dopant and A combination of fluorescent dopants may also be used.
  • luminescent dopant examples of conventionally known luminescent dopants that may be used in combination with the iridium complex compound represented by the general formula (5 ′) or (5) according to the present invention will be given as the luminescent dopant. Is not limited to these.
  • Luminescent host compound also referred to as luminescent host or host compound
  • the host compound has a mass ratio of 20% or more in the layer, and the phosphorescence quantum yield of phosphorescence emission is 0 at room temperature (25 ° C.). Defined as less than 1 compound.
  • 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 light-emitting host 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 known light emitting host may be used alone, or a plurality of types may be used in combination.
  • the movement of charges can be adjusted, and the organic EL element can be made highly efficient.
  • it becomes possible to mix different light emission by using multiple types of the metal 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 light emitting host used in the present invention may be a low molecular compound, a high molecular compound having a repeating unit, or a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (polymerizable light emitting host). It is also possible to use one or a plurality of such compounds.
  • a compound represented by the following general formula (B) or general formula (E) is particularly preferable as a light emitting host of the light emitting layer of the organic EL device of the present invention.
  • Xa represents O or S
  • Xb, Xc, Xd and Xe each represents a hydrogen atom, a substituent or a group represented by the following general formula (C)
  • Xb , Xc, Xd and Xe represent a group represented by the following general formula (C)
  • at least one of the groups represented by the following general formula (C) represents Ar as a carbazolyl group.
  • L 4 represents a divalent linking group derived from an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • n represents an integer of 0 to 3, and when n is 2 or more, the plurality of L 4 may be the same or different.
  • * represents a linking site with the general formula (B) or (E).
  • Ar represents a group represented by the following general formula (D).
  • Xf represents N (R ′′), O or S
  • E 1 to E 8 represent C (R ′′ 1 ) or N
  • R ′′ and R ′′ 1 are hydrogen atoms, substituents or it represents a linking site with L 4 in formula (C).
  • * Represents a linking site with L 4 in the general formula (C).
  • a compound represented by the following general formula (B ′) is particularly preferably used as a light-emitting host of the light-emitting layer of the organic EL device of the present invention.
  • Xa represents O or S
  • Xb and Xc each represents a substituent or a group represented by General Formula (C).
  • At least one of Xb and Xc represents a group represented by the above general formula (C), and at least one of the groups represented by the general formula (C) represents Ar as a carbazolyl group.
  • Ar in the general formula (C) represents a carbazolyl group which may have a substituent, and more preferably, in the general formula (C).
  • Ar may have a substituent and represents a carbazolyl group linked to L 4 in formula (C) at the N-position.
  • the compound represented by the general formula (B ′) that is preferably used as the host compound (also referred to as a light-emitting host) of the light-emitting layer of the organic EL device of the present invention is specifically a specific example that is previously used as a light-emitting host. OC-9, OC-11, OC-12, OC-14, OC-18, OC-18, OC-29, OC-30, OC-31, and OC-32 mentioned above, but the present invention is not limited thereto. .
  • 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 one of conventionally known compounds 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, Ring tetracarboxylic anhydride, carbodiimide, fluorenylidenemethane derivative, anthraquinodimethane and anthrone derivative, oxadiazole derivative, carboline derivative, or at least carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative Derivatives having a ring structure, one of which is substituted with a nitrogen atom, hexaazatriphenylene derivatives and the like.
  • polycyclic aromatic hydrocarbons such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, Ring tetracarboxylic anhydride, carbod
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, or 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 also 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 layer 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 complex or a metal compound such as a metal halide may be doped.
  • 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 layer thickness is usually selected in the range of 10 to 5000 nm, preferably 50 to 200 nm.
  • a transparent or semi-transparent cathode can be produced by producing a conductive transparent material mentioned in the explanation of the anode described later on the cathode after producing the metal with a layer thickness of 1 to 20 nm. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
  • 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, it exists between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. May be.
  • An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance.
  • Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) ) ”, Chapter 2,“ Electrode Materials ”(pages 123 to 166), which has a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • anode buffer layer hole injection layer
  • copper phthalocyanine is used.
  • 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 layer thickness is preferably in the range of 0.1 to 5000 nm, although it depends on the material.
  • ⁇ Blocking layer hole blocking layer, electron blocking layer>
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on November 30, 1998)” on page 237. There is a hole blocking (hole blocking) layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the structure of the electron transport layer described above can be used as a hole blocking layer according to the present invention, if necessary.
  • the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
  • the hole blocking layer 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 mentioned as the host compound described above. It is preferable to contain (represented by).
  • the light emitting layer having the shortest wavelength of light emission is preferably closest to the anode among all the light emitting layers.
  • 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.
  • the ionization potential is defined by the energy required to emit electrons at the HOMO (highest occupied orbital) level of the compound to the vacuum level, and can be determined by, for example, the following method.
  • Gaussian 98 Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.
  • a molecular orbital calculation software manufactured by Gaussian, USA.
  • eV unit converted value As a value (eV unit converted value) calculated by performing structure optimization using B3LYP / 6-31G *. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
  • the ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy. For example, a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd. or a method known as ultraviolet photoelectron spectroscopy can be suitably used.
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved.
  • the structure of the hole transport layer described later can be used as an electron blocking layer as necessary.
  • the 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 one of hole injection or transport and electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • azatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as 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 described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used.
  • these materials are preferably used because a light-emitting element with higher efficiency can be obtained.
  • the hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can.
  • the layer thickness of the hole transport layer is not particularly limited, but is usually about 5 to 5000 nm, preferably 5 to 200 nm.
  • the hole transport layer may have a single layer structure composed of one or more of the above materials.
  • a hole transport layer having a high p property doped with impurities can 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.
  • anode As the anode in the organic EL element, 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. Specific examples of such electrode substances include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) that can form a transparent conductive film may be used.
  • the anode may be a thin film 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 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.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the layer thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
  • a support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. May be opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.
  • polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones Cycloolefin resins such as polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, 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 further, oxygen measured by a method according to JIS K 7126-1987.
  • a high barrier film having a permeability of 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less and a water vapor permeability of 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less is preferable.
  • the material for forming the barrier film may be any material as long as it has a function of suppressing entry 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 device of the present invention is preferably 1% or more, and 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.
  • a thin film made of a desired electrode material for example, a material for an anode is formed on a suitable substrate so as to have a thickness of 1 ⁇ m or less, preferably 10 to 200 nm, thereby producing 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.
  • the 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 high suitability for a roll-to-roll method such as a die coating method, a roll coating method, an ink jet method, and a spray coating method is preferable.
  • a different film formation method may be applied for each layer.
  • 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 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 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 the reverse order.
  • the organic EL device of the present invention it is preferable to produce 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.
  • ⁇ 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 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 a method according to JIS K 7129-1992. It is preferable that the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) measured in (1) is 1 ⁇ 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less.
  • sealing member For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.
  • the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant may be dispersed in the adhesive.
  • Application of the adhesive to the sealing portion may use a commercially available dispenser, or may be printed like screen printing.
  • the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
  • the material for forming the film may be 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 may be used. it can.
  • vacuum deposition sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma
  • a polymerization method a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil
  • a vacuum is also possible.
  • a hygroscopic compound can also be enclosed inside.
  • hygroscopic compound examples include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
  • metal oxides for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
  • sulfates for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate.
  • metal halides eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.
  • perchloric acids eg perchloric acid Barium, magnesium perchlorate, and the like
  • anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
  • a protective film or a protective plate may be provided outside the sealing film on the side facing the support substrate with the organic layer interposed therebetween or on the outside of the sealing film.
  • the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, and the like used for the sealing can be used, but the polymer film is light and thin. Is preferably used.
  • the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light undergoes total reflection between the light and the light, and the light is guided through the transparent electrode or the light emitting layer.
  • a method of improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate and preventing total reflection at the transparent substrate and the air interface (US Pat. No. 4,774,435), A method for improving efficiency by giving light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on the side surface of an element (Japanese Patent Laid-Open No. 1-220394), light emission from a substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the bodies (Japanese Patent Laid-Open No.
  • these methods can be used in combination with the organic EL device of the present invention.
  • a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • the light extracted from the transparent electrode has a higher extraction efficiency to the outside as the refractive index of the medium is lower.
  • the low refractive index layer examples include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.
  • the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low-refractive index layer is reduced when the thickness of the low-refractive index medium is about the wavelength of light and the thickness of the electromagnetic wave exuded by evanescent enters the substrate.
  • the method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.
  • This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
  • Light that cannot be emitted due to total internal reflection between layers is diffracted by introducing a diffraction grating in any layer or medium (in a transparent substrate or transparent electrode), and the light is removed. I want to take it out.
  • the diffraction grating to be introduced has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much.
  • the refractive index distribution a two-dimensional distribution
  • the light traveling in all directions is diffracted, and the light extraction efficiency is increased.
  • the position where the diffraction grating is introduced may be in any 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 so as to provide, for example, a microlens array structure, or combined with a so-called condensing sheet, for example, with respect to a specific direction, for example, the device light emitting surface.
  • a specific direction for example, the device light emitting surface.
  • quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably 10 to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
  • the condensing sheet for example, a sheet that has been put into practical use for an LED backlight of a liquid crystal display device can be used.
  • a sheet for example, a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • BEF brightness enhancement film
  • the shape of the prism sheet for example, the base material may be formed by forming a ⁇ -shaped stripe with 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 / film may be used in combination with the light collecting sheet.
  • 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 a display device, a display, and various light emission sources.
  • lighting devices home lighting, interior lighting
  • clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light
  • the light source of a sensor etc. are mentioned, It is not limited to this, It can use effectively for the use as a backlight of a liquid crystal display device, and an illumination light source especially.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like as needed during film formation.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned.
  • a conventionally known method is used. Can do.
  • the light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with a total of CS-1000 (manufactured by Konica Minolta Sensing Co., Ltd.) is applied to the CIE chromaticity coordinates.
  • the display device of the present invention will be described.
  • 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, but here, the multicolor display device will be described.
  • a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by 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 included 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 in the one aspect
  • a DC voltage When a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state.
  • the alternating current waveform to be applied may be arbitrary.
  • the multicolor display device can be used as a display device, a display, and various light 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.
  • Display devices and displays include televisions, personal computers, mobile devices, AV devices, teletext displays, information displays in automobiles, and the like. In particular, it may be used as a display device for reproducing still images and moving images, and 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, and the like.
  • the control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside, and the pixels for each scanning line respond to the image data signal by the scanning signal.
  • the image information is sequentially emitted to scan the image and display the image information on the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A.
  • the display unit A includes a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate.
  • the main members of the display unit A will be described below.
  • FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).
  • 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) When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6 and emits light according to the received image data. Full-color display is possible by appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
  • FIG. 3 is a schematic diagram of a pixel.
  • the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
  • 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.
  • the power supply line 7 connects the organic EL element 10 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 elements 10 of the plurality of pixels, and the organic EL elements 10 of the plurality of pixels 3 emit light. 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 diagram 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 lighting device of the present invention has the said organic EL element.
  • the organic EL element of the present invention may be used as an organic EL element having a resonator structure.
  • the purpose of use of the organic EL element having such a resonator structure is as follows.
  • the light source of a machine, the light source of an optical communication processing machine, the light source of a photosensor, etc. are mentioned, However It is not limited to these. Moreover, you may use for the said use by making a laser oscillation.
  • the organic EL device of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display). When used as a display device for reproducing moving images, either a simple matrix (passive matrix) method or an active matrix method may be used. Alternatively, it is possible to produce a full-color display device by using two or more organic EL elements of the present invention having different emission colors.
  • the organic EL material of the present invention can be applied to an organic EL element that emits substantially white light as a lighting device.
  • a plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials to obtain white light emission by color mixing.
  • As a combination of a plurality of light emission colors one containing three light emission maximum wavelengths of three primary colors of red, green, and blue may be used, or two of the complementary colors such as blue and yellow, blue green and orange may be used. The thing containing the light emission maximum wavelength may be used.
  • a combination of light emitting materials for obtaining a plurality of emission colors is a combination of a plurality of phosphorescent or fluorescent materials, a light emitting material that emits fluorescence or phosphorescence, and light from the light emitting material as excitation light.
  • a plurality of light emitting dopants may be mixed and mixed.
  • an electrode film can be formed by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, or the like, and productivity is also improved. According to this method, unlike the white organic EL device in which light emitting elements of a plurality of colors are arranged in parallel in an array, the elements themselves are luminescent white.
  • luminescent material used for a light emitting layer For example, if it is a backlight in a liquid crystal display element, the metal complex which concerns on this invention so that it may suit the wavelength range corresponding to CF (color filter) characteristic, Any one of known luminescent materials may be selected and combined to whiten.
  • CF color filter
  • One aspect of the lighting device of the present invention that includes the organic EL element of the present invention will be described.
  • the non-light emitting surface of the organic EL device of the present invention is covered with a glass case, a 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. 5 shows a schematic diagram of a lighting device, and the organic EL element 101 of the present invention is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is to bring the organic EL element 101 into contact with the atmosphere. And a glove box under a nitrogen atmosphere (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more).
  • FIG. 6 shows a cross-sectional view of the lighting device.
  • 105 denotes a cathode
  • 106 denotes an organic EL layer
  • 107 denotes a glass substrate with a transparent electrode.
  • the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
  • This ITO transparent electrode was patterned after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (Indium Tin Oxide) as an anode on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm.
  • the transparent support substrate provided with was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • PEDOT / PSS polystyrene sulfonate
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of ⁇ -NPD is placed in a molybdenum resistance heating boat as a hole transport material and OC-as a host compound in another molybdenum resistance heating boat.
  • 200 mg of 30 was put, 200 mg of ET-8 as an electron transport material was put in another resistance heating boat made of molybdenum, and 100 mg of Comparative 1 was put as a dopant compound in another resistance heating boat made of molybdenum, and attached to a vacuum deposition apparatus.
  • the vacuum chamber was then depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing ⁇ -NPD, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second, with a layer thickness of 20 nm.
  • the second hole transport layer was provided.
  • the heating boat containing OC-30 as a host compound and Comparative Example 1 as a dopant compound was energized and heated, and on the second hole transport layer at a deposition rate of 0.1 nm / second and 0.006 nm / second, respectively.
  • a light emitting layer having a layer thickness of 40 nm was provided by co-evaporation.
  • the heating boat containing ET-8 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a layer thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride was vapor-deposited to form a cathode buffer layer having a layer thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a layer thickness of 110 nm.
  • an organic EL element 1-1 was produced.
  • the organic EL device 1-13 of the present invention shows higher luminous efficiency and longer life than the organic EL devices 1-1 and 1-2 of the comparative example, and the voltage rise during driving. It can be seen that the characteristics as an element are improved. Furthermore, the organic EL elements 1-1 and 1-2 of the comparative example are the elements manufactured for the first time, the elements manufactured for the third time, the elements manufactured for the fifth time, and the half-life is gradually reduced. On the other hand, the organic EL device 1-13 of the present invention is almost the same as the first device, the third device, the fifth device, and the half-life. It can be seen that the dopant compound used in the organic EL device of the present invention is excellent in thermal stability.
  • Preparation of white light-emitting organic EL element 2-1 A transparent substrate provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) as an anode on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm.
  • the supporting substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of ⁇ -NPD is placed in a molybdenum resistance heating boat as a hole transport material and OC-as a host compound in another molybdenum resistance heating boat.
  • each of the heating boats containing ⁇ -NPD was separately energized, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second.
  • a first hole transport layer was provided.
  • the deposition rate of Compound 9, Comparative 1, and D-10 was 100: 5: 0.6.
  • the light emitting layer was provided by vapor deposition so as to have a layer thickness of 30 nm.
  • the heating boat containing ET-11 was energized and heated, and was deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a layer thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride was vapor-deposited to form a cathode buffer layer having a layer thickness of 0.5 nm
  • aluminum was further vapor-deposited to form a cathode having a layer thickness of 110 nm to produce an organic EL element 2-1.
  • the organic EL element 2-9 of the present invention exhibits higher luminous efficiency and longer life than the organic EL elements 2-1 and 2-2 of the comparative example, and suppresses a voltage increase during driving. It turns out that the characteristic as an element is improving. Furthermore, the organic EL elements 2-1 and 2-2 of the comparative example are the elements manufactured for the first time, the elements manufactured for the third time, the elements manufactured for the fifth time, and the half-life is gradually reduced. On the other hand, the organic EL device 2-9 of the present invention is almost the same as the first device, the third device, the fifth device, and the half-life. It can be seen that the dopant compound used in the organic EL device of the present invention is excellent in thermal stability.
  • FIG. 7 shows a schematic configuration diagram of an organic EL full-color display device.
  • a hole injection layer composition having the following composition is ejected and injected on the ITO electrode 202 between the partition walls 203 using an inkjet head (manufactured by Epson Corporation; MJ800C), irradiated with ultraviolet light for 200 seconds, and 60 ° C.
  • a hole injection layer 204 having a layer thickness of 40 nm was provided by a drying process for 10 minutes (see FIG. 7C).
  • a blue light-emitting layer composition, a green light-emitting layer composition, and a red light-emitting layer composition having the following compositions are similarly ejected and injected onto the hole injection layer 204 using an inkjet head, and dried at 60 ° C. for 10 minutes.
  • light emitting layers 205B, 205G, and 205R for each color were provided (see FIG. 7D).
  • an electron transport material (ET-10) is deposited so as to cover each of the light emitting layers 205B, 205G, and 205R to provide an electron transport layer (not shown) having a layer thickness of 20 nm, and further lithium fluoride is deposited to form a layer.
  • a cathode buffer layer (not shown) with a thickness of 0.6 nm was provided, Al was vapor-deposited, and a cathode 106 with a layer thickness of 130 nm was provided to produce an organic EL device (see FIG. 7E).
  • the produced organic EL elements showed blue, green, and red light emission by applying a voltage to the electrodes, respectively, and were found to be usable as a full-color display device.
  • the dopant of the present invention since the dopant of the present invention has a high carrier transport property, the driving voltage does not increase greatly even in a region where the dopant concentration is low, and the external extraction quantum efficiency is also high. On the other hand, high external quantum efficiency and half-life are obtained even in a high doping concentration region, which is presumed to be because the dispersibility of the dopant of the present invention is improved and aggregation is suppressed. Furthermore, due to the effects described above, the element according to the present invention is less dependent on the concentration of the dopant in the external quantum efficiency, the driving voltage, and the half-life compared to the comparative example.
  • ⁇ Preparation of organic EL element 5-1 A transparent substrate provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) as an anode on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm.
  • the supporting substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • PEDOT / PSS polystyrene sulfonate
  • This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of ⁇ -NPD as a hole transport material was placed in a molybdenum resistance heating boat, and Compound 30 as a host compound was placed in another molybdenum resistance heating boat.
  • the vacuum chamber was then depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing ⁇ -NPD, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second, with a layer thickness of 20 nm.
  • the second hole transport layer was provided.
  • the heating boat containing the compound 30 as the host compound, the comparison 3 as the blue dopant compound and the D-10 as the red dopant was energized and heated, and the deposition rates were 0.1 nm / second, 0.010 nm / second, 0, respectively.
  • a light emitting layer having a layer thickness of 40 nm was provided by co-evaporation on the second hole transport layer at a rate of .0002 nm / second.
  • the compound 24 was deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a hole blocking layer having a layer thickness of 5 nm.
  • the heating boat containing ET-8 was energized and heated, and deposited on the hole blocking layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a layer thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride was vapor-deposited to form a cathode buffer layer having a layer thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a layer thickness of 110 nm.
  • an organic EL element 5-1 was produced.
  • the dopant of the present invention has high emission efficiency, good emission lifetime in a region where the dopant concentration is high, and small chromaticity shift during continuous driving.
  • a quartz substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • This quartz substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus. Meanwhile, 200 mg of OC-29 as a host compound was put in a molybdenum resistance heating boat, and 100 mg of Comparative 4 was put as a dopant in another resistance heating boat made of molybdenum. It was attached to a vacuum evaporation system.
  • the heating boat containing OC-29 and Comparative 4 was energized and heated, and the deposition rate was 0.1 nm / second and 0.005 nm / second, respectively.
  • the organic EL element 6-1 was obtained by co-evaporation on a quartz substrate to provide a light-emitting layer having a thickness of 40 nm.
  • concentration of the comparison 4 after vapor deposition was 5%.
  • the measurement was performed with a Hitachi spectrophotometer U-3300 and a fluorimeter F-4500.
  • the peak areas obtained in the organic EL elements 6-1 and 6-4 having a dopant concentration of 5% were set to 100, and evaluation was performed by comparing the cases where the dopant concentrations were 15% and 25%.
  • the dopant of the present invention exhibits high PL intensity even in a region where the dopant concentration is high. This is presumably because the dispersibility of the dopant of the present invention is high and aggregation is suppressed even in a high concentration region. Furthermore, the organic EL elements 6-3 and 6-6 were also evaluated for stability during storage at high temperature and high humidity as described below.
  • the dopant of the present invention exhibits high PL strength even after storage, and has high stability during storage at high temperature and high humidity.
  • a poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) diluted to 70% with pure water was used to spin. After forming a thin film by the coating method, it was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a layer thickness of 30 nm.
  • a hole transport material Poly N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- A thin film was formed by spin coating using the chlorobenzene solution of No. 254). Heat drying at 150 ° C. for 1 hour to provide a second hole transport layer having a layer thickness of 30 nm.
  • This transparent support substrate was fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of OC-29 as a host compound was put in a molybdenum resistance heating boat, and ET-42 was used as an electron transport material in another molybdenum resistance heating boat. 200 mg was added, and 100 mg of Comparative 2 was added as a dopant to another molybdenum resistance heating boat and attached to a vacuum deposition apparatus.
  • the vacuum chamber was then depressurized to 4 ⁇ 10 ⁇ 4 Pa, and then heated by energizing the heating boat containing OC-29 as a host compound and Comparative 2 as a dopant, respectively, with a deposition rate of 0.1 nm / second, 0.
  • a light-emitting layer having a layer thickness of 40 nm was provided by co-evaporation on the second hole transport layer at 009 nm / second.
  • the heating boat containing ET-42 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a layer thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride was vapor-deposited to form a cathode buffer layer having a layer thickness of 0.5 nm, and aluminum was further vapor-deposited to form a cathode having a layer thickness of 110 nm.
  • an organic EL element 7-1 was produced.
  • the organic EL elements 7-3 to 7-16 of the present invention show higher luminous efficiency and longer life than the organic EL elements 7-1 and 7-2 of the comparative examples, and the voltage rise during driving It can be seen that the characteristics of the device are improved, such as suppressing the above.
  • the present invention improves the thermal stability and sublimation property of an organometallic complex as an organic electroluminescence element material, thereby providing a light-emitting efficiency and a long-life organic electroluminescence element, and illumination using the element Suitable for providing a device and a display device.
  • the present invention is suitable for solving the problem of chromaticity stability (chromaticity shift) during continuous driving in a white light emitting organic electroluminescence device and improving the doping concentration dependency in device performance.
  • an iridium complex compound having high dispersibility it is suitable for extending the lifetime of the organic electroluminescence device.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/JP2013/050892 2012-02-02 2013-01-18 Composé complexe d'iridium, matériau pour élément électroluminescent organique, élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage Ceased WO2013114966A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013235994A (ja) * 2012-05-10 2013-11-21 Konica Minolta Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JPWO2014038677A1 (ja) * 2012-09-07 2016-08-12 出光興産株式会社 新規芳香族複素環誘導体、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子用材料溶液及び有機エレクトロルミネッセンス素子
JP2018181916A (ja) * 2017-04-04 2018-11-15 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器及び照明装置
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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010135467A (ja) * 2008-12-03 2010-06-17 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置
US20110057559A1 (en) * 2007-12-28 2011-03-10 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
US20110204333A1 (en) * 2010-02-25 2011-08-25 Universal Display Corporation Phosphorescent emitters

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5157916B2 (ja) * 2007-01-26 2013-03-06 コニカミノルタホールディングス株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5347262B2 (ja) * 2007-11-22 2013-11-20 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、表示装置及び照明装置
JP5742586B2 (ja) * 2011-08-25 2015-07-01 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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110057559A1 (en) * 2007-12-28 2011-03-10 Universal Display Corporation Phosphorescent emitters and host materials with improved stability
JP2010135467A (ja) * 2008-12-03 2010-06-17 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置
US20110204333A1 (en) * 2010-02-25 2011-08-25 Universal Display Corporation Phosphorescent emitters

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013235994A (ja) * 2012-05-10 2013-11-21 Konica Minolta Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JPWO2014038677A1 (ja) * 2012-09-07 2016-08-12 出光興産株式会社 新規芳香族複素環誘導体、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子用材料溶液及び有機エレクトロルミネッセンス素子
JP2018181916A (ja) * 2017-04-04 2018-11-15 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器及び照明装置
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
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

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