Organometallic complex, organic light-emitting element, display device, imaging device, electronic device, lighting device, mobile device, and method for manufacturing an organic light-emitting element.
The organometallic complex with specific aromatic substituents addresses trap site formation and luminescence quantum yield loss in platinum dinuclear complexes, enhancing performance in organic light-emitting devices by reducing molecular aggregation and improving exciton energy efficiency.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- CANON KK
- Filing Date
- 2025-01-17
- Publication Date
- 2026-07-30
AI Technical Summary
The platinum dinuclear complex described in Non-Patent Literature 1 is prone to trap site formation and a decrease in luminescence quantum yield due to concentration quenching, particularly under high doping concentrations in organic light-emitting devices.
An organometallic complex represented by general formulas (1) or (2), featuring specific aromatic substituents and π-π interactions between molecules, is developed to reduce trap site formation and luminescence quantum yield loss.
The organometallic complex effectively suppresses the decrease in luminescence quantum yield at high doping concentrations by minimizing molecular aggregation and enhancing exciton energy utilization.
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Abstract
Description
Technical Field
[0001] The present invention relates to an organometallic complex, an organic light-emitting device, a display device, an imaging device, an electronic device, a lighting device, a moving body, and a method for manufacturing an organic light-emitting device.
Background Art
[0002] An organic light-emitting device is an electronic device having a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. By injecting electrons and holes from these pair of electrodes, excitons of a light-emitting organic compound in the organic compound layer are generated, and when the excitons return to the ground state, the organic electroluminescent device emits light. According to the spin statistics rule, 75% of the energy of the excitons becomes triplet energy, so a phosphorescent light-emitting material that emits light from the triplet excited state is known to have a high luminescence quantum yield. Among phosphorescent light-emitting materials, a dinuclear platinum complex having a ligand with a highly planar structure is a material particularly having a high luminescence quantum yield. The level required for the luminescence quantum yield of phosphorescent light-emitting materials has been increasing year by year, and in order to further improve the luminescence quantum yield, attempts have been made to improve its structure. Non-Patent Document 1 describes the following dinuclear platinum complex 1.
[0003]
Chemical Formula
Prior Art Documents
Non-Patent Documents
[0004]
Non-Patent Document 1
Summary of the Invention
Problems to be Solved by the Invention
[0005] The platinum dinuclear complex 1 described in Non-Patent Literature 1 is prone to trap site formation and a decrease in luminescence quantum yield due to concentration quenching, due to its high planarity. When used in the luminescence layer of an organic light-emitting device, the above problems are particularly likely to occur under high doping concentration conditions.
[0006] This invention has been made in view of the above problems, and aims to provide an organometallic complex in which the formation of trap sites and the decrease in luminescence quantum yield due to concentration quenching are reduced. [Means for solving the problem]
[0007] The present invention provides an organometallic complex characterized by being represented by the following general formula (1) or the following general formula (2).
[0008] [ka]
[0009] In general formula (1), A is selected from carbon atoms and silicon atoms.
[0010] Each ring B is independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.
[0011] L is selected from carbon, nitrogen, oxygen, and sulfur atoms. n is either 0 or 1.
[0012] Ring C is a substituted or unsubstituted heteroaryl ring, and PtL1 and PtL2 are independently bidentate ligands represented by the following general formula (3).
[0013] [ka]
[0014] In general formula (3), R1 to R3 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.
Advantages of the Invention
[0015] According to the present invention, it is possible to provide an organometallic complex in which the formation of trap sites and the decrease in the luminescence quantum yield due to concentration quenching are reduced.
Brief Description of the Drawings
[0016] [Figure 1] (a) is a schematic cross-sectional view showing an example of a pixel of a display device according to an embodiment of the present invention. (b) is a schematic cross-sectional view of an example of a display device using an organic light-emitting element according to an embodiment of the present invention. [Figure 2] It is a schematic diagram showing an example of a display device according to an embodiment of the present invention. [Figure 3] (a) is a schematic diagram showing an example of an imaging device according to an embodiment of the present invention. (b) is a schematic diagram showing an example of an electronic device according to an embodiment of the present invention. [Figure 4] (a) is a schematic diagram showing an example of a display device according to an embodiment of the present invention. (b) is a schematic diagram showing an example of a foldable display device. [Figure 5] (a) is a schematic diagram showing an example of a lighting device according to an embodiment of the present invention. (b) is a schematic diagram showing an example of an automobile having a vehicle lamp according to an embodiment of the present invention. [Figure 6] (a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. (b) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, in a form having an imaging device.
Embodiments for Carrying Out the Invention
[0017] The present invention will be described in detail below with reference to preferred embodiments. It will be readily apparent to those skilled in the art that the present invention is not limited to the following description, and that its form and details can be modified in various ways without departing from the spirit and scope of the invention. In other words, the present invention should not be construed as being limited by the following description.
[0018] <Organometallic complexes> The organometallic complex according to the present invention is represented by the following general formula (1) or general formula (2). In general formula (1), ring B is independently selected from a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. In general formula (2), ring D is a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. That is, because aromatic substituents are substituted at specific positions, aggregation of organometallic complexes due to the size of their molecular volume can be reduced. Furthermore, since the utilization efficiency of exciton energy is improved due to π-π interactions between molecules, the decrease in luminescence quantum yield at high doping concentrations of the organometallic complex is suppressed.
[0019] [ka]
[0020] In general formula (1), A is selected from a carbon atom and a silicon atom. Each ring B is independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, and L is selected from a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom. If L is a carbon atom or a nitrogen atom, the carbon atom or nitrogen atom may have substituents. n is 0 or 1. Each ring C is independently a substituted or unsubstituted heteroaryl ring. PtL1 and PtL2 are independently bidentate ligands represented by the following general formula (3).
[0021] [ka]
[0022] In general formula (3), R1 to R3 are independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.
[0023] [ka]
[0024] In general formula (2), A is selected from carbon atoms and silicon atoms. Ring C is a substituted or unsubstituted teloaryl ring, ring D is independently selected from a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, and PtL1 and PtL2 are independently bidentate ligands represented by the above general formula (3).
[0025] In general formula (1), ring B is independently selected from substituted or unsubstituted aryl rings and substituted or unsubstituted heteroaryl rings.
[0026] In general formula (1), ring B is independently selected from a substituted or unsubstituted aryl ring and a substituted or unsubstituted heteroaryl ring. The aryl ring of ring B may be an aryl ring having 6 to 30 carbon atoms, and may be a monoring or a fused ring. In particular, the aryl ring of ring B in general formula (1) is preferably a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a 9,9-spirobifluorene ring, or a chrysene ring. The heteroaryl ring of ring B may be a heteroaryl ring having 6 to 30 carbon atoms, and may be a monoring or a fused ring. In particular, the heteroaryl ring of ring B in general formula (1) is preferably a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring. The substituents that ring B may have represent a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an aryloxy group, a heteroaryloxy group, a silyl group, an alkoxycarbonyl group, an acyl group, and a cyano group.
[0027] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine. Of these, fluorine is preferred from the viewpoint of thermal stability.
[0028] Examples of alkyl groups include linear or branched alkyl groups having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, sec-butyl, and octyl groups. Alkyl groups may have substituents within a range that does not impair the emission quantum yield. Examples of such substituents include halogen atoms, cyano groups, and nitro groups. Furthermore, one or more non-adjacent methylene groups of an alkyl group may be substituted with -O-, -S-, -C(=O)-, -C(=O)O-, -O(C=O)-, -CH=CH-, or -C≡C-.
[0029] Examples of cycloalkyl groups include those having 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 6 carbon atoms. Specific examples of cycloalkyl groups include cyclopropyl groups and cyclohexyl groups. Cycloalkyl groups may have substituents within a range that does not impair the emission quantum yield. Examples of such substituents include halogen atoms, cyano groups, and nitro groups.
[0030] Examples of alkoxy groups include alkoxy groups having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms. Specific examples of alkoxy groups include methoxy groups, ethoxy groups, propoxy groups, and 2-ethyl-octyloxy groups. The alkoxy group may have substituents within a range that does not impair the emission quantum yield. Examples of such substituents include halogen atoms, cyano groups, nitro groups, benzyl groups, and naphthyl groups. Examples of halogen atoms are the same as those described as halogen atoms among the substituents that ring B in general formula (1) may have.
[0031] Examples of aryl groups include aryl groups having 6 to 30 carbon atoms, and may be monocyclic or fused rings. Specific examples of aryl groups include phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, carbazolyl, dibenzofuryl, and dibenzothienyl groups. The aryl group may further have substituents to the extent that it does not impair the emission quantum yield. Such substituents may be halogen atoms, cyano groups, nitro groups, alkyl groups, alkoxy groups, benzyl groups, and naphthyl groups, or combinations thereof. Examples of halogen atoms, alkyl groups, and alkoxy groups are the same as those described for the substituents that ring B in general formula (1) may have.
[0032] Examples of heteroaryl groups include heteroaryl groups having 3 to 15 atoms constituting the ring, and may be monocyclic or fused rings. Examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and germanium atoms, and may contain multiple atoms of these. Specific examples of heteroaryl groups include pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, and phenanthrolyl groups. Heteroaryl groups may have substituents as long as they do not impair the luminescence quantum yield. Such substituents may include, for example, halogen atoms, cyano groups, nitro groups, alkyl groups, alkoxy groups, benzyl groups, and naphthyl groups, or combinations thereof. Examples of halogen atoms, alkyl groups, and alkoxy groups are the same as those described as substituents that ring B in general formula (1) may have.
[0033] Examples of aryloxy groups include those in which the aryl portion has 6 to 30 carbon atoms. Specifically, examples of aryloxy groups include phenoxy groups and naphthoxy groups. The aryloxy group may be substituted with a halogen atom, a cyano group, an alkyl group, or an alkoxy group. Examples of halogen atoms, alkyl groups, and alkoxy groups are the same as those described as substituents that ring B in general formula (1) may have.
[0034] Examples of heteroaryloxy groups include heteroaryloxy groups having 3 to 15 atoms constituting the ring of the heteroaryl moiety, and may be monocyclic or fused rings. Examples of heteroatoms include those similar to those described as heteroatoms of the heteroaryl group among the substituents that ring B in general formula (1) may have. Specific examples of heteroaryloxy groups include pyridyloxy, pyrimidyloxy, pyrazyloxy, triazyloxy, benzofuryloxy, dibenzofuryloxy, benzothienyloxy, dibenzothienyloxy, pyryloxy, indolyloxy, and N-methylcarbazolyloxy.
[0035] A silyl group is a group in which an alkyl group, aryl group, or alkoxy group is substituted on a silicon atom. Examples of silyl groups include trialkylsilyl groups, dialkylarylsilyl groups, alkyldiarylsilyl groups, and triarylsilyl groups. Among these, silyl groups substituted with an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 10 carbon atoms are preferred. Specifically, examples include trimethylsilyl groups, triphenylsilyl groups, tert-butyldimethylsilyl groups, triisopropylsilyl groups, and tert-butyldiphenylsilyl groups.
[0036] Examples of acyl groups include those having 1 to 20 carbon atoms. Specifically, examples of acyl groups include the formyl group, acetyl group, propionyl group, and benzoyl group.
[0037] Examples of alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 20 carbon atoms. Specific examples of alkylcarbonyl groups include methoxycarbonyl groups, ethoxycarbonyl groups, and hexyloxycarbonyl groups.
[0038] In general formula (1), L is selected from a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom. If L is a carbon atom or a nitrogen atom, the carbon atom or nitrogen atom may have substituents. The substituents are selected from linear or branched alkyl groups having 1 to 6 carbon atoms, fluorine atoms, silyl groups, aryl groups, and heteroaryl groups.
[0039] The alkyl groups that L may have as substituents include, specifically, methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, and sec-butyl groups. Of these, methyl, i-propyl, and tert-butyl groups are preferred.
[0040] The aryl group that L may have as a substituent is the same as the aryl group described as one of the substituents that ring B in general formula (1) may have. Of these, the phenyl group and the trimethylphenyl group are preferred.
[0041] The heteroaryl group that L may have as a substituent is the same as the aryl group described as one of the substituents that ring B in general formula (1) may have. Of these, the carbazolyl group is preferred.
[0042] In general formula (1), n is either 0 or 1. When n is 0, it indicates that the rings B are directly bonded to each other. To further suppress the decrease in the luminescence quantum yield of organometallic complexes at high doping concentrations, it is preferable that n be 0 from the viewpoint of ligand rigidity.
[0043] In general formulas (1) and (2), ring C is a substituted or unsubstituted heteroaryl ring. If there are multiple heteroaryl groups, they may be the same or different.
[0044] Each ring C is bonded to a Pt atom by one N atom. Ring C is a substituted or unsubstituted heteroaryl ring, similar to those described as ring B in general formula (1). Among these, pyridine rings, pyrazine rings, pyrimidine rings, pyrrole rings, pyrazole rings, triazole rings, and benzoquinoline rings are preferred.
[0045] The substituents that ring C may have are selected from linear or branched alkyl groups having 1 to 6 carbon atoms, fluorine groups, silyl groups, aryl groups, and heteroaryl groups, and may be in combination thereof. Furthermore, adjacent substituents may be bonded together.
[0046] The alkyl groups that can be substituents on ring C include, specifically, methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, and sec-butyl groups. Of these, methyl, i-propyl, and tert-butyl groups are preferred.
[0047] The aryl group as a substituent on ring C is the same as the aryl group described as a substituent that ring B in general formula (1) may have. Of these, the phenyl group and the trimethylphenyl group are preferred.
[0048] The heteroaryl group as a substituent on ring C is the same as the aryl group described as one of the substituents that ring B in general formula (1) may have. Of these, the carbazolyl group is preferred.
[0049] In general formula (2), ring D is independently selected from a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. Examples of this aryl ring and heteroaryl ring are the same as those described for ring B in general formula (1). Of these, a phenyl group, a naphthalene group, a dibenzofuranyl group, or a dibenzothiophenyl group is preferred.
[0050] In general formulas (1) and (2), PtL1 and PtL2 are bidentate ligands represented by general formula (3). In general formula (3), R1 to R3 are independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. Examples of halogen atoms, alkyl groups, cycloalkyl groups, alkoxy groups, aryl groups, and heteroaryl groups represented by R1 to R3 are the same as those described for each group of ring B in general formula (1). Among these, from the viewpoint of thermal stability, R1 and R3 are preferably the alkyl groups described above.
[0051] Specific examples of compounds represented by general formula (1) and general formula (2) are shown below. Of course, in the present invention, the following specific examples are not limited to those that fall under the definitions of general formula (1) and general formula (2).
[0052] [ka]
[0053] [ka]
[0054] [ka]
[0055] [ka]
[0056] <Configuration of an organic light-emitting element> An example of an organic light-emitting element is one having a structure in which an insulating layer, a first electrode, an organic compound layer, and a second electrode are laminated on a substrate in this order. A protective layer and a color filter may be provided on the second electrode (in the direction opposite to the substrate). If a color filter is provided, a planarization layer may be provided between the protective layer and the color filter. One of the first electrode and the second electrode is the anode and the other is the cathode.
[0057] (substrate) The substrate can be made of materials such as quartz, glass, silicon, resin, and metal. Alternatively, switching elements such as transistors and wiring may be placed on the substrate, and an insulating layer may be provided on top of them. The insulating layer can be made of any material that allows for the formation of contact holes to ensure conductivity between the anode and the wiring, and provides insulation from wiring that should not be connected. Specific examples of insulating layers include those made of resins such as polyimide, and silicon compounds such as silicon oxide and silicon nitride.
[0058] (electrode) An organic electroluminescent device is provided with a pair of electrodes. These electrodes are the anode and the cathode. When a voltage is applied in the direction of light emission, the electrode with the higher potential becomes the anode, and the other becomes the cathode. Alternatively, the electrode supplying holes to the light-emitting layer can be considered the anode, and the electrode supplying electrons can be considered the cathode.
[0059] The anode is preferably composed of materials with a high work function. Examples include metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten; metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide; mixtures and alloys thereof; and conductive polymers such as polyaniline, polypyrrole, and polythiophene. The electrode may be composed of one or more materials. The anode may also be composed of one or more layers.
[0060] For use as a reflective electrode, the anode can be made from materials such as metals like chromium, aluminum, silver, titanium, tungsten, and molybdenum; alloys or laminates of these metals can also be used. For use as a transparent electrode, oxides such as indium tin oxide (ITO) and indium zinc oxide can be used as the anode material. Photolithography can be used to form the anode.
[0061] On the other hand, materials with a small work function are preferred for the cathode. Examples include alkali metals such as lithium; alkaline earth metals such as calcium; other metals such as aluminum, titanium, manganese, silver, lead, and chromium; oxides, mixtures, and alloys thereof. Examples of alloys include magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-lithium, silver-copper, and zinc-silver. Metal oxides such as indium tin oxide (ITO) may also be used. One or more types of materials may be used for the electrode components. The cathode may also be composed of one or more layers. Among these, the use of silver is preferred, and a silver alloy is even more preferred in order to suppress silver aggregation. The ratio of the alloy is not a concern as long as silver aggregation is suppressed. For example, it may be 1:1.
[0062] The cathode may be a top-emission element using an oxide conductive layer such as indium tin oxide (ITO), or a bottom-emission element using a reflective electrode such as aluminum (Al). Photolithography can also be used to form the cathode. Among these methods, sputtering (DC or AC) is preferred for forming the cathode. This is because the film formed by sputtering has excellent coverage and makes it easy to reduce resistance.
[0063] (protective layer) The protective layer can be provided on the cathode. For example, by bonding a glass with a desiccant layer onto the cathode, the intrusion of water and other substances into the organic compound layer can be suppressed, thereby preventing display defects. Alternatively, a passivation film such as silicon nitride may be provided on the cathode to suppress the intrusion of water and other substances into the organic compound layer. The protective layer can be formed by chemical vapor deposition (CVD). Alternatively, after film formation by chemical vapor deposition, a two-layer protective layer may be provided by atomic deposition (ALD). For example, after forming the cathode, it can be transported to another chamber while maintaining a vacuum, and a silicon nitride film can be formed as a protective layer by CVD. The thickness of the protective layer is preferably 1 to 10 μm.
[0064] (Color filter) The color filter can be placed on top of the protective layer. For example, a color filter corresponding to the size of the organic electroluminescent element may be placed on a separate substrate and bonded to the substrate on which the organic electroluminescent element is placed, or the color filter may be patterned using photolithography technology. The color filter can be made of polymer material or the like.
[0065] (flattening layer) A planarization layer can be provided between the color filter and the protective layer. Examples of constituent materials for the planarization layer include organic compounds, with high-molecular-weight organic compounds being preferred. The planarization layer may be provided on both sides of the color filter, in which case the constituent materials of each planarization layer may be the same or different. Examples of constituent materials for the planarization layer include resins such as polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.
[0066] (Opposite substrate) The opposing substrate can be placed on top of the planarization layer. Because the opposing substrate is placed opposite the substrate, it is called an opposing substrate. The constituent materials of the opposing substrate are the same as those listed for the constituent materials of the substrate.
[0067] (organic compound layer) Next, an organic compound layer having an organic light-emitting element according to one embodiment of the present invention will be described.
[0068] The organic light-emitting element according to this embodiment comprises at least a pair of electrodes, a first electrode and a second electrode, and an organic compound layer disposed between these electrodes. In the organic light-emitting element of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer. The pair of electrodes may be an anode and a cathode.
[0069] If the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have an emissive layer. In addition to the emissive layer, the organic compound layer may also have a hole injection layer, a hole transport layer, an electron blocking layer, a hole-exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the emissive layer may be a single layer or a laminate consisting of multiple layers. The hole transport layer and electron transport layer are also called charge transport layers.
[0070] In the organic light-emitting element of this embodiment, at least one layer of the organic compound layer contains a luminescent composition. Specifically, the luminescent composition is contained in any of the hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole-exciton blocking layer, electron transport layer, electron injection layer, etc., and is preferably contained in the light-emitting layer. The transport layers between the first electrode and the light-emitting layer can be collectively called the first charge transport layer. The transport layers between the second electrode and the light-emitting layer can be collectively called the second charge transport layer. That is, the light-emitting layer is in contact with the first charge transport layer and the second charge transport layer.
[0071] In the organic light-emitting element of this embodiment, when the luminescent composition is included in the light-emitting layer, the light-emitting layer may consist only of an organometallic complex, or it may be a layer having an organometallic complex and an organic compound different from the organometallic complex. Preferably, the organometallic complex has a minimum excitation triplet energy lower than the minimum excitation triplet energy of the charge transport material. The organic compound used in the light-emitting layer together with the organometallic complex may have a minimum excitation triplet energy equal to or greater than the minimum excitation triplet energy of the organometallic complex. Here, when the light-emitting layer is a layer having an organometallic complex and an organic compound, the organic compound may be the host material of the light-emitting layer. The organometallic complex may also be a guest material or a dopant material. The organic compound may also be an assist material.
[0072] Here, the host material is a compound that is primarily responsible for charge injection and transport in the light-emitting layer. In organic light-emitting devices, the host material itself may not emit light substantially. Preferably, it is a compound with a phosphorescent emission quantum yield of less than 0.1% at room temperature (25°C), and more preferably, a compound with an emission quantum yield of less than 0.01%. The guest material or dopant material is a compound that is primarily responsible for light emission in the organic light-emitting device. The assist material is a compound that, by mass, is present in smaller quantities than the host and guest materials among the compounds constituting the light-emitting layer, and assists the light emission of the guest. The assist material is also called the second host material.
[0073] Here, the dope concentration according to this embodiment refers to the mass % concentration relative to the mass of the guest host. The dope concentration is preferably 50% by mass or more and 100% by mass or less.
[0074] In addition to the above-mentioned materials, the luminescent composition may contain various additives as needed, such as charge transporters, resins, plasticizers, antioxidants, and ultraviolet absorbers. Among these, it is preferable to include resins and charge transport materials (e.g., electron transport materials). The resin is preferably a binder resin. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin. The resin may be a homopolymer or copolymer, and one or more resins may be used. Known materials can be used as electron transport materials. For example, 1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl]benzene can be used. Commercially available electron transport materials (e.g., trade name "OXD-7," manufactured by Lumnescence Technology) can also be used.
[0075] The luminescent composition may also be a liquid. To make a liquid luminescent composition, an organic solvent must be included. The organic solvent is not particularly limited as long as it can dissolve or disperse the compound of the present invention. In particular, it is preferable to use an organic solvent having a boiling point of 70°C to 300°C at 1 atmosphere. The content (mass%) of the organic solvent in the liquid luminescent composition is preferably 85% to 99% by mass, based on the total mass of the luminescent composition.
[0076] Examples of organic solvents include toluene, o-xylene, p-xylene, mesitylene, chlorobenzene, dichlorobenzene, diethyl ether, dibutyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, anisole, 4-methylanisole, phenylcyclohexane, dimethoxyethane, diethylene glycol dimethyl ether, ethyl acetate, butyl acetate, methyl benzoate, cyclopentanone, cyclohexanone, dimethylformamide, dimethylacetamide, methyl ethyl ketone, N-methylpyrrolidone, and dimethylimidazolidinone. One or more organic solvents can be used to adjust various properties in the luminescent composition, such as the compatibility of various materials, the viscosity of the liquid, and the surface tension.
[0077] Furthermore, it is preferable that the lowest excited triplet energy of the charge transport layer is greater than the lowest excited triplet energy of the host material. Also, it is preferable that the lowest excited triplet energy of the second charge transport layer is greater than the lowest excited triplet energy of the first organic compound. The lowest excited triplet energy of a charge transport layer can be estimated using the lowest excited triplet energy of the constituent materials of that layer. If the charge transport layer is composed of multiple materials, it may be the lowest excited triplet energy of the compound with the largest weight ratio.
[0078] The inventors conducted various studies and found that using the organometallic complex according to this embodiment as a guest in the light-emitting layer yields high efficiency. This light-emitting layer may be a single layer or a multi-layer, and it is also possible to mix it with the light-emitting color of this embodiment by including light-emitting materials having other light-emitting colors. A multi-layer means a state in which multiple light-emitting layers are stacked. In this case, the light-emitting color of the organic light-emitting element is not limited to the same hue as the light-emitting color of the single layer. More specifically, it may be white or an intermediate color. In the case of white, white may be achieved by emitting red, blue, and green light in each light-emitting layer, or by combining light-emitting colors that are in a complementary color relationship.
[0079] The organometallic complex according to this embodiment can also be used as a constituent material for organic compound layers other than the light-emitting layer constituting the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material for electron transport layers, electron injection layers, hole transport layers, hole injection layers, hole blocking layers, etc. If there are multiple light-emitting layers, a charge generation layer may be provided between the light-emitting layers. The charge generation layer may be composed of a compound whose LUMO energy is lower than that of the hole transport layer. In other words, the LUMO energy of the charge generation layer may be lower than the HOMO energy of the hole transport layer. Here, the molecular orbital energy of the organic compound layer may be the molecular orbital energy of the organic compound with the largest weight ratio in the organic compound layer.
[0080] Here, the HOMO energy level and LUMO energy level are described as "higher" the closer they are to the vacuum level. When the LUMO energy of the charge generation layer is lower than the HOMO energy of the hole transport layer, it means that the LUMO energy of the charge generation layer is further from the vacuum level than the HOMO energy of the hole transport layer.
[0081] In this specification, HOMO and LUMO can be calculated using molecular orbital calculations. These calculations are performed using Density Functional Theory (DFT), with the functional being B3LYP and the basis set being 6-31G. *For example, the range of graphical designs is provided by Gaussian09(Gaussian09, RevisionC.01,MJFrisch,GWTrucks,HBSchlegel,GEScuse ria, MARobb,JRCheeseman,G.Scalmani,V.Barone,B.Mennucci,GAPetersson,H.Nakatsuji,M.Caricato,X.Li,HPHra tchian, AFIzmaylov, J. Bloino, G. Zheng, JLSonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishi da,T.Nakajima,Y.Honda,O.Kitao,H.Nakai,T.Vreven,JAMontgomery,Jr.,JEPeralta,F.Ogliaro,M.Bearpark,JJHe yd, E. Brothers, KNKudin, VNS Taroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, JCBurant ,SSIyengar,J.Tomasi,M.Cossi,N.Rega,JMMillam,M.Klene,JEKnox,JBCross,V.Bakken,C.Adamo,J.Jaramillo,R.G omperts,REStratmann,O.Yazyev,AJAustin,R.Cammi,C.Pomelli,JWOchterski,RLMartin,K.Morokuma,VGZakrzews ki,GAVoth,P.Salvador,JJDannenberg,S.Dapprich,ADDaniels,O.Farkas,JBForesman,JVOrtiz,JCioslowski,and DJFox,Gaussian,Inc.,Wallingford CT,2010.)
[0082] In this specification, HOMO and LUMO can be calculated using the ionization potential and band gap. The HOMO can be estimated by measuring the ionization potential. The ionization potential can be measured using a measuring device such as AC-3 after dissolving the compound to be measured in a solvent such as toluene, or after depositing the compound onto a substrate such as glass. The band gap can be measured by dissolving the compound to be measured in a solvent such as toluene and irradiating it with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum of the excitation light. Alternatively, the compound to be measured can be deposited onto a substrate such as glass, and the band gap can be measured by irradiating the deposited film with excitation light. The measurement can be performed by measuring the absorption edge of the absorption spectrum where the deposited film absorbs the excitation light.
[0083] The LUMO can be calculated using the band gap and ionization potential. By subtracting the ionization potential from the band gap, the LUMO can be estimated.
[0084] LUMO can also be estimated from the reduction potential. For example, the one-electron reduction potential can be estimated using cyclic volmetry (CV) measurement. CV measurement is performed, for example, in a 0.1 M tetrabutylammonium perchlorate DMF solution with an Ag / Ag reference electrode. + The measurement can be performed using Pt as the counter electrode and glassy carbon as the working electrode. The LUMO can be estimated by adding the difference of -4.8 eV between the reduction potential of the obtained compound and the reduction potential of ferrocene.
[0085] When manufacturing an organic light-emitting element according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injection compounds or hole-transport compounds, host compounds, luminescent compounds, electron-injection compounds or electron-transport compounds, etc., can be used together as needed. Examples of these compounds are given below.
[0086] As hole-implantation transport materials, materials with high hole mobility are preferred to facilitate hole injection from the anode and to transport the injected holes to the light-emitting layer. Furthermore, materials with a high glass transition temperature are preferred to reduce film quality degradation such as crystallization in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole-implantation transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, polyarylamine derivatives, polyvinylcarbazole derivatives, polythiophene derivatives, conductive polymers such as PEDOT-PSS, and copolymers or mixtures thereof. Moreover, the above-mentioned hole-implantation transport materials are also suitably used in electron-blocking layers.
[0087] The following are specific examples of compounds used as hole-injection transportable materials, but of course, they are not the only ones.
[0088] [ka]
[0089] [ka]
[0090] In addition to the organometallic complex according to one embodiment of the present invention, other luminescent materials can also be added as luminescent materials primarily involved in the luminescence function. Other luminescent materials include fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, iridium complexes such as tris(2-phenylpyridinate)iridium, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of compounds used as luminescent materials are shown below, but are not limited to these.
[0091] [ka]
[0092] [ka]
[0093] Examples of assisting materials included in the light-emitting layer include aromatic hydrocarbon compounds or their derivatives, as well as polymers such as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triazine derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, organoberylium complexes, polyphenylene derivatives, polyphenylenevinylene derivatives, polyfluorene derivatives, and polyvinylcarbazole derivatives, or copolymers or mixtures thereof.
[0094] The following are specific examples of compounds used as assist materials in the light-emitting layer, but of course, they are not the only ones that can be used.
[0095] [ka]
[0096] [ka]
[0097] As electron-transporting materials, any material capable of transporting electrons injected from the cathode to the light-emitting layer can be arbitrarily selected, taking into consideration the balance with the hole mobility of the hole-transporting material. Examples of materials with electron-transporting properties include oxadiazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron-transporting materials are also suitably used in the hole-blocking layer.
[0098] The following are specific examples of compounds used as electron transport materials, but of course, they are not the only ones.
[0099] [ka]
[0100] Electron-injectable materials can be arbitrarily selected from those that allow for easy electron injection from the cathode, taking into consideration the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. Examples include alkali metal compounds such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fluvalene derivatives, and acridine derivatives.
[0101] <Method for manufacturing organic field-emitting element> A method for manufacturing an organic field light-emitting device having an organic compound layer (such as a hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer) is described. The organic field light-emitting device is manufactured by a manufacturing method that includes the step of applying a light-emitting composition to a substrate to form an organic compound layer.
[0102] Methods for forming an organic compound layer include, for example, dry processes and wet processes. Dry processes include, for example, vacuum deposition, ionization deposition, sputtering, and plasma deposition. Wet processes include, for example, coating methods such as spin coating, casting, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, capillary coating, and spray coating; and known printing methods such as screen printing, flexographic printing, offset printing, and inkjet printing.
[0103] As methods for forming organic compound layers, vacuum deposition, ionization deposition, spray coating, and inkjet methods are preferred from the viewpoint of achieving both film uniformity in thin film formation with a thickness of several nanometers and the formation of large-area pixels. Furthermore, from the viewpoint of material utilization efficiency and manufacturing cost, spray coating and inkjet methods are preferred.
[0104] It is preferable to form an organic compound layer by a wet process and then dry the organic solvent. The drying conditions can be appropriately set according to the constituent materials such as the organic compound layer. It is preferable to dry in an air or inert gas (nitrogen, argon, etc.) atmosphere. The heating temperature for drying is preferably 100°C to 250°C, and more preferably 110°C to 200°C. The heating time for drying is preferably 5 minutes to 60 minutes. The pressure during heating for drying may be at normal pressure (1 atmosphere) or under reduced pressure (100 PA to 0.1 MPa). The various conditions (temperature, pressure, and time) in the drying process should be set so that the organic solvent can be removed from the organic compound layer, etc.
[0105] When forming an organic compound layer by a wet process using a liquid luminescent composition, it is preferable to appropriately determine the composition. The content (mass%) of the organic solvent as an organic solvent in the luminescent composition is preferably 10.0 to 100.0 times the total mass ratio of the content (mass%) of the solid components constituting the organic compound layer. Examples of solid components constituting the organic compound layer include organometallic complexes and charge transport materials.
[0106] When applying a liquid luminescent composition to a substrate using an inkjet method to form an organic compound layer, it is preferable to appropriately control its physical properties. The surface tension of the liquid luminescent composition at 25°C is preferably 15 mN / m to 75 mN / m, and more preferably 25 mN / m to 45 mN / m. The surface tension of the liquid luminescent composition can be adjusted by appropriately determining the type and content of the organic solvent in the luminescent composition. Furthermore, the viscosity of the liquid luminescent composition at 25°C is preferably 0.1 mPA·s to 20.0 mPA·s, and more preferably 0.5 mPA·s to 10.0 mPA·s. By setting the viscosity within the above range, clogging and ejection failures in the liquid ejection head during inkjet ejection can be suppressed.
[0107] <Pixel Circuit> The organic light-emitting device may have a pixel circuit connected to an organic electroluminescent element. The pixel circuit is preferably an active-matrix type that independently controls the light emission of each of the multiple organic electroluminescent elements. The active-matrix circuit may be voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may further include a transistor for controlling the light emission brightness of the organic electroluminescent element, a transistor for controlling the light emission timing, a capacitor for holding the gate voltage of the transistor controlling the light emission brightness, and a transistor for connecting to ground without going through the organic electroluminescent element.
[0108] The organic light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit. The slope of the current-voltage characteristic of the transistors constituting the pixel circuit may be smaller than the slope of the current-voltage characteristic of the transistors constituting the display control circuit. The slope of the current-voltage characteristic can be measured by the so-called Vg-Ig characteristic. The transistors constituting the pixel circuit are transistors connected to the organic electroluminescent device.
[0109] <Pixel> The organic light-emitting device has multiple pixels. Each of the multiple pixels has sub-pixels that emit light of a different color from the others. Each sub-pixel independently has an RGB emission color. The pixels emit light in a region also called the pixel aperture. The pixel aperture is preferably 15 μm or less, and preferably 5 μm or more. For example, the pixel aperture can be 11.0 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc. The distance between sub-pixels is preferably 10 μm or less. For example, the distance between sub-pixels can be 8.0 μm, 7.4 μm, 6.4 μm, etc.
[0110] The planar arrangement of pixels can be a known form. Specifically, examples include stripe arrangement, delta arrangement, pentile arrangement, and Bayer arrangement. The planar shape of subpixels can be a known shape. Specifically, examples include rectangles, rhombuses, and other quadrilaterals and hexagons. Here, the planar shape of subpixels does not need to be an exact figure; if it is close to a rectangle, it will be judged as a rectangle. The planar shape of subpixels and the pixel arrangement can be used in combination.
[0111] <Applications of organic electroluminescent devices> Organic electroluminescent elements can be used as components in display devices and lighting equipment. Other applications include exposure light sources for electrophotographic image recording devices, backlights for liquid crystal display devices, and light-emitting devices with color filters in a white light source.
[0112] The display device includes an image input unit that receives image information from an area CCD, linear CCD, memory card, etc., and an information processing unit that processes the input information. The display device may also be an image information processing unit that displays the input image on a display unit. Furthermore, the display unit of the imaging device or inkjet recording device may have a touch panel function. Specific examples of drive methods for the touch panel function include infrared, capacitive, resistive, and electromagnetic induction methods. The display device may also be used as the display unit of a so-called hybrid recording device.
[0113] Next, the display device will be described with reference to the drawings. Figure 1(A) is a schematic cross-sectional view of an example of a pixel constituting the display device. The pixel has sub-pixels 10. The sub-pixels 10 are divided into 10R, 10G, and 10B based on their light emission. The emitted color may be distinguished and determined by the wavelength emitted from the light-emitting layer, or it may be determined by selective transmission or color conversion of the light emitted from the sub-pixels 10 using a color filter or the like. Each sub-pixel 10 has a reflective electrode 2 which is the first electrode, an insulating layer 3 covering the end of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, a transparent electrode 5, a protective layer 6, and a color filter 7 on an interlayer insulating layer 1.
[0114] The interlayer insulating layer 1 may have transistors or capacitive elements placed beneath or inside it in the direction shown in the illustration. The transistors and the first electrode may be electrically connected via contact holes or the like (not shown). The insulating layer 3 is also called a bank or pixel isolation layer. The insulating layer 3 covers the end of the first electrode and is arranged surrounding the first electrode. The portion where the insulating layer 3 is not placed is in contact with the organic compound layer 4 and becomes a light-emitting region. The organic compound layer 4 has a hole injection layer 41, a hole transport layer 42, a first light-emitting layer 43, a second light-emitting layer 44, and an electron transport layer 45. The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode. The protective layer 6 reduces the penetration of liquid components such as water into the organic compound layer. The protective layer is shown as a single layer, but may consist of multiple layers. If it consists of multiple layers, it may include inorganic compound layers and organic compound layers. The color filter 7 is divided into 7R, 7G, and 7B according to its color. The color filter may be formed on a planarization film (not shown). Alternatively, the color filter may have a resin protective layer (not shown). Furthermore, the color filter may be formed on the protective layer 6, or it may be bonded to an opposing substrate such as a glass substrate after being provided on it.
[0115] Figure 1(B) is a schematic cross-sectional view showing an example of a display device comprising an organic electroluminescent element and a transistor connected to the organic electroluminescent element. The transistor is an example of an active element. The transistor may also be a thin-film transistor (TFT). The display device 100 in Figure 1(B) consists of a substrate 11 made of glass, silicon, or the like, and an insulating layer 12 provided on top of the substrate 11. An active element 18, such as a TFT, is arranged on top of the insulating layer 12, and the gate electrode 13, gate insulating film 14, and semiconductor layer 15 of the active element are arranged thereon. The TFT 18 consists of a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. The anode 21 and the source electrode 17 constituting the organic electroluminescent element are connected via contact holes 20 provided in the insulating film. Note that the method of electrical connection between the electrodes (anode, cathode) included in the organic electroluminescent element and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the embodiment shown in Figure 1(B). In other words, it is sufficient that the anode or cathode is electrically connected to the TFT source electrode or drain electrode.
[0116] In the display device 100 shown in Figure 1(B), the organic compound layer is depicted as a single layer, but the organic compound layer 22 may consist of multiple layers. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce the degradation of the organic electroluminescent element. In the display device 100 shown in Figure 1(B), a transistor is used as the switching element, but other switching elements may be used instead.
[0117] Furthermore, the transistor used in the display device 100 in Figure 2(B) is not limited to a transistor using a single-crystal silicon wafer, but may also be a thin-film transistor having an active layer on the insulating surface of the substrate. Examples of the active layer include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide.
[0118] The transistors included in the display device 100 in Figure 1(B) may be formed within a substrate such as a silicon substrate. Forming within a substrate means that the transistors are manufactured by processing a substrate such as a silicon substrate. In other words, having transistors within a substrate can be seen as the substrate and transistors being formed as a single unit.
[0119] The organic electroluminescent element's luminescence is controlled by a TFT, which is an example of a switching element. By arranging multiple organic electroluminescent elements on a surface, an image is displayed based on the luminescence of each element. The switching element is not limited to a TFT; it may also be a transistor made of low-temperature polysilicon or an active matrix driver formed on a substrate such as a silicon substrate. The term "top or inside the substrate" can also be interpreted as "within the substrate." Whether to provide a transistor within the substrate or use a TFT is selected depending on the size of the display area. For example, if the size is about 0.5 inches, it is preferable to provide the organic electroluminescent element on a silicon substrate.
[0120] Figure 2 is a schematic diagram representing an example of a display device. The display device 1000 has a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. Flexible printed circuits FPCs 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005. Transistors are printed on the circuit board 1007. If the display device is a portable device, a battery 1008 is provided. Alternatively, the battery 1008 may be provided in a different location.
[0121] The display device may have a color filter having red, green, and blue colors. The color filter may be arranged in a delta array, a stripe array, or a mosaic array.
[0122] The display device can be used in the display section of a mobile device. In this case, it may have both display and operation functions. Examples of mobile devices include smartphones and other mobile phones, tablets, and head-mounted displays.
[0123] The display device can be used in the display unit of an imaging device having an optical unit with multiple lenses and an image sensor that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the image sensor. The display unit may be an external display unit or a display unit located inside the viewfinder. The imaging device may be a digital camera or a digital video camera. The imaging device may also be called a photoelectric converter.
[0124] Figure 3(a) is a schematic diagram showing an example of an imaging device. The imaging device 1100 includes a viewfinder 1101, a rear display 1102, an operating unit 1103, and a housing 1104. The viewfinder 1101 can use a display device. In that case, the display device may display not only the image to be captured, but also environmental information, imaging instructions, etc. Environmental information may include the intensity of ambient light, the direction of ambient light, the speed at which the subject is moving, and the possibility that the subject may be obscured by an obstruction.
[0125] Since the optimal timing for imaging is only a short time, it is preferable to be able to display information quickly. Because organic electroluminescent elements have a fast response speed, the display device using the organic electroluminescent elements of the present invention can be suitably applied. The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses and forms an image on the image sensor housed in the housing 1104. The focus can be adjusted by adjusting the relative positions of the multiple lenses. This operation can also be performed automatically.
[0126] Figure 3(b) is a schematic diagram representing an example of an electronic device. The electronic device 1200 has a display unit 1201, an operating unit 1202, and a housing 1203. The housing 1203 has a circuit, a printed circuit board with the circuit, a battery, and a communication unit. The operating unit 1202 may be a button or a touch panel type response unit. The operating unit 1202 may also be a biometric recognition unit that recognizes fingerprints to unlock the device. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an image sensor. In this case, the image captured by the camera function is displayed on the display unit 1201. Examples of electronic devices 1200 include smartphones and laptop computers.
[0127] Figure 4 is a schematic diagram showing an example of a display device. Figure 4(a) is a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301, a display unit 1302, and a base that supports the display unit 1302. The display unit 1302 uses a light-emitting device. The base 1303 is not limited to the form shown in Figure 4(A), and the lower edge of the frame 1301 may also serve as the base. In addition, the frame 1301 and the display unit 1302 may be curved. The radius of curvature is preferably 5,000 mm or more and 6,000 mm or less.
[0128] Figure 4(b) is a schematic diagram representing another example of a display device. The display device 1310 in Figure 4(b) is configured to be foldable and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may be light-emitting devices. The first display unit 1311 and the second display unit 1312 may be a single display device without seams. The first display unit 1311 and the second display unit 1312 can be separated at the bending point. The first display unit 1311 and the second display unit 1312 may each display different images or may display a single image.
[0129] Figure 5(a) is a schematic diagram showing an example of a lighting device. The lighting device 1400 includes a housing 1401, a light source 1402, a circuit board 1403, an optical film 1404, and a light diffusion unit 1405. An organic electroluminescent element can be used as the light source. The optical filter may be a filter that improves the color rendering of the light source. The light diffusion unit effectively diffuses the light from the light source, such as for lighting up, and can deliver light over a wide area. The optical filter and light diffusion unit may be provided on the light output side of the lighting. A cover may be provided on the outermost part as needed.
[0130] A lighting device is, for example, a device for illuminating a room, and comprises a light source and a component that transmits the light emitted by the light source. The lighting device may emit light in any color from blue to red, not just white or cool white. Here, "white" refers to a color temperature of 4,200K, and "cool white" refers to a color temperature of 5,000K. The lighting device may have a dimming circuit to adjust the brightness. The lighting device may also have an organic electroluminescent element and a power supply circuit connected thereto. The power supply circuit is a circuit that converts AC voltage to DC voltage. The lighting device may have a light diffuser or a color filter as a component that transmits the light emitted by the light source. The lighting device may also have a heat dissipation section. The heat dissipation section releases heat from inside the device to the outside, and examples include metals with high specific heat or liquid silicon.
[0131] Figure 5(b) is a schematic diagram of an automobile, which is an example of a mobile vehicle. The automobile has a taillight, which is an example of a lighting device. The automobile 1500 may have a taillight 1501, and the taillight may be configured to illuminate when the brakes are applied or when other actions are taken.
[0132] The tail lamp 1501 may have an organic electroluminescent element. The tail lamp may also have a protective member to protect the organic electroluminescent element. Any protective member can be suitably used as long as it has a reasonably high strength and is transparent. Among these, it is preferable that it be composed of polycarbonate. A frangic acid derivative or an acrylonitrile derivative may be mixed with the polycarbonate.
[0133] The automobile 1500 may have a body 1503 and windows 1502 attached thereto. The windows may be transparent displays unless they are for checking the front and rear of the automobile. The transparent displays may have organic electroluminescent elements. In this case, the constituent materials such as electrodes having the organic electroluminescent elements are made of transparent components.
[0134] The mobile entity may be a ship, aircraft, drone, etc. The mobile entity may have a body and a light fixture installed on the body. The light fixture may emit light to indicate the position of the body. The light fixture has an organic electroluminescent element.
[0135] Refer to Figure 6 to describe examples of display device applications. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, head-mounted displays, and smart contact lenses. The imaging display device used in such applications comprises an imaging device capable of photoelectric conversion of visible light and a display device capable of emitting visible light.
[0136] Referring to Figure 6(a), the eyeglasses 1600 (smart glasses) will be described. An imaging device 1602, such as a CMOS sensor or SPAD, is provided on the front side of the lens 1601 of the eyeglasses 1600. A display device is provided on the back side of the lens 1601. The eyeglasses 1600 further includes a control device 1603. The control device 1603 functions as a power supply that provides power to the imaging device 1602 and the display device. The control device 1603 also controls the operation of the imaging device 1602 and the display device. An optical system is formed in the lens 1601 for focusing light onto the imaging device 1602.
[0137] Referring to Figure 6(b), the eyeglasses 1610 (smart glasses) will be described. The eyeglasses 1610 have a control device 1612, which is equipped with an imaging device equivalent to the imaging device 1602 and a display device. The lens 1611 has an optical system formed therein for projecting light emitted from the imaging device and display device in the control device 1612, and an image is projected onto the lens 1611. The control device 1612 functions as a power supply to supply power to the imaging device and display device, and also controls the operation of the imaging device and display device. The control device may have a gaze detection unit that detects the wearer's gaze. Gaze detection may use infrared light. The infrared light emitter emits infrared light towards the user's eyeball that is fixated on the displayed image. The imaging unit, which has a photodetector, detects the reflected light from the eyeball of the emitted infrared light, thereby obtaining an image of the eyeball. By having a reduction means that reduces the light from the infrared light emitter to the display unit in planar view, the deterioration of image quality is reduced.
[0138] The eyeglasses 1610 detect the user's gaze toward the displayed image from an image of the eyeball obtained by imaging with infrared light. Any known method can be applied to gaze detection using an image of the eyeball. As an example, a gaze detection method based on the Purkinje image obtained by the reflection of the irradiated light from the cornea can be used. Specifically, gaze detection processing based on the pupil-corneal reflection method is performed. Using the pupil-corneal reflection method, the user's gaze is detected by calculating a gaze vector representing the orientation (rotation angle) of the eyeball based on the pupil image and the Purkinje image included in the image of the eyeball.
[0139] The display device may have an imaging device with a light-receiving element, and may control the display image of the display device based on the user's gaze information from the imaging device. Specifically, the display device determines a first display area that the user is fixated on and a second display area other than the first display area based on the gaze information. The first display area and the second display area may be determined by the control device of the display device, or they may be determined by an external control device and received. In the display area of the display device, the display resolution of the first display area may be controlled to be higher than the display resolution of the second display area. In other words, the resolution of the second display area may be lower than that of the first display area.
[0140] Furthermore, the display area has a first display area and a second display area different from the first display area, and based on gaze information, the area with higher priority is determined from the first display area and the second display area. The first display area and the second display area may be determined by the control device of the display device, or they may be determined by an external control device and received. The resolution of the high-priority area may be controlled to be higher than the resolution of the areas other than the high-priority area. In other words, the resolution of areas with relatively lower priority may be lower.
[0141] AI may be used to determine the first display area and high-priority areas. The AI may be a model configured to estimate the angle of gaze and the distance to the target object in the line of sight from the image of the eye, using the image of the eye and the direction the eye was actually looking in the image as training data. The AI program may be contained in the display device, the imaging device, or an external device. If contained in an external device, it is transmitted to the display device via communication. When display control is based on visual detection, it is preferably applicable to smart glasses that further have an imaging device for capturing images of the outside. The smart glasses can display the captured external information in real time.
[0142] As described above, by using the device employing the organic light-emitting element of the present invention, it becomes possible to achieve stable display with good image quality even during long-term display. Furthermore, it becomes possible to achieve both good visibility outdoors due to high-efficiency, high-brightness light output and power-saving display.
[0143] The present invention includes the following configuration.
[0144] [Configuration 1] An organometallic complex characterized by being represented by the following general formula (1) or general formula (2).
[0145] [ka]
[0146] In general formula (1), A is either a carbon atom or a silicon atom.
[0147] Each ring B is independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.
[0148] L is selected from carbon, nitrogen, oxygen, and sulfur atoms. n is either 0 or 1.
[0149] Ring C is a substituted or unsubstituted heteroaryl ring, and PtL1 and PtL2 are independently bidentate ligands represented by the following general formula (3).
[0150] [ka]
[0151] In general formula (3), R1 to R3 are independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.
[0152] [Configuration 2] The organometallic complex according to configuration 1, characterized by being represented by the following general formula (2).
[0153] [ka]
[0154] In general formula (2), A is either a carbon atom or a silicon atom.
[0155] [Configuration 3] The organometallic complex according to configuration 1 or 2, characterized in that n is 0.
[0156] [Structure 4] The organometallic complex according to any one of configurations 1 to 3, characterized in that, in general formula (3), R1 and R3 are both alkyl groups and R2 is a hydrogen atom.
[0157] [Composition 5] The organometallic complex according to configuration 2, characterized in that, in the general formula (2), ring D is a phenyl group or a naphthalene group, and in the general formula (3), R1 and R3 are both alkyl groups and R2 is a hydrogen atom.
[0158] [Composition 6] An organometallic complex according to any one of configurations 1 to 5, characterized by being represented by any of the following structural formulas.
[0159] [ka]
[0160] [Composition 7] A luminescent composition characterized by comprising an organometallic complex according to any one of configurations 1 to 6, and a first organic compound different from the organometallic complex.
[0161] [Structure 8] The luminescent composition according to configuration 7, wherein the mass% concentration of the organometallic complex relative to the first organic compound is 50% by mass or more and 100% by mass or less.
[0162] [Composition 9] The luminescent composition according to configuration 8, wherein the first organic compound is a liquid.
[0163] [Configuration 10] An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, The organic light-emitting element is characterized in that the organic compound layer has an organometallic complex according to any one of configurations 1 to 6.
[0164] [Composition 11] The organic compound layer comprises the organometallic complex and a first organic compound different from the organometallic complex. The organic light-emitting element according to configuration 10, characterized in that the lowest excited triplet energy of the first organic compound is equal to or greater than the lowest excited triplet energy of the organometallic complex.
[0165] [Composition 12] The aforementioned organic compound layer is a light-emitting layer, A first charge transport layer is disposed between the first electrode and the light-emitting layer, The device comprises a second charge transport layer disposed between the second electrode and the light-emitting layer, The organic light-emitting element according to configuration 11, characterized in that the lowest excited triplet energy of the first charge transport layer is greater than the lowest excited triplet energy of the first organic compound, and the lowest excited triplet energy of the second charge transport layer is greater than the lowest excited triplet energy of the first organic compound.
[0166] [Composition 13] A display device having a plurality of pixels and transistors connected to the plurality of pixels, wherein at least one of the plurality of pixels is an organic light-emitting element according to any one of the configurations 10 to 12.
[0167] [Composition 14] An imaging device comprising an optical section having multiple lenses, an image sensor that receives light that has passed through the optical section, and a display section that displays an image captured by the image sensor, wherein the display section includes an organic light-emitting element as described in any one of the configurations 10 to 12.
[0168] [Composition 15] An electronic device comprising a display unit, a housing on which the display unit is provided, and a communication unit provided in the housing for communicating with the outside, wherein the display unit includes an organic light-emitting element as described in any one of the configurations 10 to 12.
[0169] [Composition 16] A lighting device comprising a light source and a member that transmits light emitted by the light source, wherein the light source includes an organic light-emitting element as described in any one of the configurations 10 to 12.
[0170] [Composition 17] A mobile body having a light fixture and a body on which the light fixture is provided, wherein the light fixture includes an organic light-emitting element as described in any one of the configurations 10 to 12. [Examples]
[0171] Examples are described below. However, the present invention is not limited to these examples.
[0172] (1) Synthesis Examples The synthesis methods for Example Compound 1, Comparative Example Compound 1, and Comparative Example Compound 2 are shown below.
[0173] <Method for synthesizing example compound 1> (Synthesis of tetradentate ligand related to example compound 1)
[0174] [ka]
[0175] 1.26 g (3 mmol, 1.0 eq) of the starting material, 1.42 g (3.0 eq) of 2-chloropyridine, 35.0 mg (0.03 eq) of tetrakis(triphenylphosphine)palladium(0), and 950 mg (3.0 eq) of sodium carbonate were weighed into a 100 mL three-necked round-bottom flask, and degassed under reduced pressure / Ar substitution was performed five times. After sufficient degassing under reduced pressure and nitrogen substitution, 20 mL of toluene, 5.0 mL of ethanol, and 3.0 mL of water were added under a nitrogen atmosphere, and the mixture was refluxed and stirred at 74 °C for 8 hours. After heating was stopped, the reaction mixture was allowed to return to room temperature. After extraction with toluene three times, the organic solvent layers were collected, anhydrous sodium sulfate was added, and the mixture was allowed to stand for a while. The sodium sulfate was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was passed through silica gel short column chromatography using toluene as the eluent, and the fraction containing the target product was recovered and concentrated under reduced pressure. The obtained oil was subjected to silica gel column chromatography using heptane-toluene as the eluent, and the fraction containing the intermediate was recovered and concentrated under reduced pressure. The presence of the intermediate was confirmed by MALDI-MS (m / z = 486.17).
[0176] The tetradentate ligands for example compounds 10, 17, 27, 29, 30, 46, 50, 51, comparative example compound 1, and comparative example compound 2 were synthesized using the same method as for example compound 1. The structural formulas of each starting material 1 and starting material 2 used in the synthesis, as well as the structural formulas, yields, and identification data of each tetradentate ligand are shown in Table 1 below.
[0177] [Table 1]
[0178] (Synthesis of intermediate related to example compound 1)
[0179] [ka]
[0180] The aforementioned tetradentate ligand [1.16 g, 2.40 mmol] and K2PtCl4 [1.86 g, 1.5 eq] were added to a mixed solvent (20 ml ethoxyethanol, 5 ml water) and heated and stirred at 90°C for 10 hours under a nitrogen atmosphere. The dark red precipitate was filtered and washed with methanol to obtain a dark yellow powder. For the sake of simplicity, a tetranuclear complex is shown in the reaction scheme, but it is possible that a polynuclear complex with 6 or more nuclei was formed. No identification was performed, and the next synthesis step was carried out.
[0181] The intermediates for example compounds 10, 17, 27, 29, 30, 46, 50, 51, comparative example compound 1, and comparative example compound 2 were synthesized using the same method as for the intermediate for example compound 1 described above.
[0182] (Synthesis of the final product related to Exemplary Compound 1)
[0183] [ka]
[0184] The above intermediate [0.25 mmol (assumed to be a tetranuclear complex)] and auxiliary ligands [368 mg, 2 mmol] were added to 10 ml of ethoxyethanol, refluxed and stirred under a nitrogen stream at 90°C for 5 hours, then heating was stopped and the reaction mixture was allowed to return to room temperature. After extraction three times with dichloromethane, the organic solvent layers were collected, anhydrous sodium sulfate was added, and the mixture was allowed to stand for a while. The sodium sulfate was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was passed through silica gel short column chromatography using toluene as the eluent, and the fraction containing the target product was recovered and concentrated under reduced pressure. The obtained oil was passed through silica gel column chromatography using heptane-toluene as the eluent, and the fraction containing the final product was recovered and concentrated under reduced pressure. The final product was confirmed by MALDI-MS (m / z = 1242.38).
[0185] The final products for Exemplary Compounds 10, 17, 27, 29, 30, 46, 50, 51, Comparative Example Compound 1, and Comparative Example Compound 2 were synthesized using the same method as for Exemplary Compound 1. The structural formulas of each starting material 1 and 2 used in the synthesis, as well as the structural formulas, yields, and identification data of each final product are shown in Tables 2-1 and 2-2 below.
[0186] [Table 2-1]
[0187] [Table 2-2]
[0188] <Preparation of liquid luminescent compositions> Each component (unit: mass%) shown in Table 3 was mixed and thoroughly stirred to dissolve. Then, pressure filtration was performed using a filter with a pore size of 0.2 μm to prepare each luminescent composition. • Organometallic complexes (types shown in Table 3): Usage amount (mass%) shown in Table 3 • Host material (EM33): Usage amount (mass%) shown in Table 3 • Organic solvent (toluene): 99.0 (mass%)
[0189] [Table 3]
[0190] <Preparation of neat membrane N by spin coating method> Next, thin films (neat films N) with a doping concentration of 100.0% by mass of each organometallic complex were fabricated using the spin coating method. The fabrication conditions were as follows: • Coating solution: Luminescent compositions No. 1, 4, 7, 10, 13, 16, 19, 22, 25, 28, and 31 listed in Table 3. • Spin court conditions: 3,000 rpm, 60 seconds Annealing conditions: 110°C, 10 minutes • Film thickness: 10nm <Preparation of doped film D1 and doped film D2 by spin coating method> Next, thin films with doping concentrations of 5.0 mass% of each organometallic complex (doped film D1) and 50.0 mass% (doped film D2) were fabricated by spin coating. The fabrication conditions were as follows. • Coating solution: Luminescent compositions No. 2, 3, 5, 6, 8, 9, 11, 12, 14, 15, 17, 18, 20, 21, 23, 24, 26, 27, 29, 30, 32, 33 listed in Table 3. • Spin court conditions: 3,000 rpm, 60 seconds Annealing conditions: 110°C, 10 minutes • Film thickness: 10nm <Preparation of neat film N by vapor deposition method> A thin film (neat film N) with a dope concentration of 100.0% by mass of Exemplary Compound 1 was deposited onto a quartz substrate by vacuum deposition under conditions of a vacuum of 5 × 10⁻⁶ Pa or less. The thickness of the light-emitting layer was 10 nm. Neat films N of Exemplary Compounds 10, 17, 27, 29, 30, 46, 50, 51, Comparative Example Compound 1, and Comparative Example Compound 2 were prepared using the same method as described above.
[0191] <Deposition of doped films D1 and D2 by vapor deposition method> On a quartz substrate, Exemplary Compound 1 and EM33 were deposited from different deposition sources using a vacuum deposition method under conditions of a vacuum of 5 × 10⁻⁶ Pa or less. Thin films with a doping concentration of Exemplary Compound 1 of 5.0 mass% (doped film D1) and thin films with a doping concentration of 50.0 mass% (doped film D2) were prepared with a thickness of 10 nm. Doped films D1 and D2 were prepared for Exemplary Compounds 10, 17, 27, 29, 30, 46, 50, 51, Comparative Example Compound 1, and Comparative Example Compound 2, respectively, using the same method as described above.
[0192] <Rating> For each neat film and each doped film obtained, the luminescence quantum yield (LQY) of the neat film (hereinafter also referred to as PLQY(N)), the luminescence quantum yield of doped film D1 (hereinafter also referred to as PLQY(D1)), and the luminescence quantum yield of doped film D2 (hereinafter also referred to as PLQY(D2)) were measured. The measurement conditions were 346 nm excitation light, 400-550 nm host emission region, and 550-800 nm dopant emission region, and the measurements were performed using an absolute luminescence quantum yield analyzer (product name "C11347-01", manufactured by Hamamatsu Photonics). From the PLQY(N)PLQY(D1) and PLQY(D2) values obtained from the above measurements, PLQY(N) / PLQY(D1) and PLQY(N) / PLQY(D2) were calculated, and the ratio of the luminescence quantum yield of the neat film to the dopant of the doped film was evaluated according to the evaluation criteria shown below. Larger values for PLQY(N) / PLQY(D1) and PLQY(N) / PLQY(D2) indicate that the reduction in luminescence quantum yield due to the aggregation of organometallic complexes is being suppressed. A: The value of PLQY(N) / PLQY(D1) or PLQY(N) / PLQY(D2) was greater than 1.5. B: The value of PLQY(N) / PLQY(D1) or PLQY(N) / PLQY(D2) was greater than 1.0 and less than or equal to 1.5. The value of C:PLQY(N) / PLQY(D1) or PLQY(N) / PLQY(D2) was 1.0 or less.
[0193] [Table 4]
[0194] Based on the above, it has been found that the organometallic complex of the present invention is useful as a phosphorescent material that suppresses the decrease in luminescence quantum yield at high doping concentrations. [Explanation of Symbols]
[0195] Single interlayer insulating layer 2 reflective electrode 3. Insulating layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color Filters 10 subpixels 11 circuit boards 12 Insulating layer 13 gates 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrodes 18 Thin-film transistors 19 Insulating film 20 contact holes 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting diodes 27 Photoreceptor 28 Exposure light source 29 light 30 Charged parts 31. Developing Department 32 Transfer section 33 Conveying section 34 Recording media 35 Fixing section 36 Light-emitting part 37. First direction parallel to the long axis of the photoreceptor. 40 Image forming apparatus 100 display device 1000 display devices 1001 Top cover 1002 Flexible Printed Circuits 1003 Touch Panel 1004 Flexible Printed Circuit 1005 Display Panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation unit 1104 cabinet 1200 Electronic equipment 1201 Display section 1202 Operation unit 1203 enclosure 1300 display device 1301 Picture frame 1302 Display section 1303 Base 1310 Display device 1311 First display section 1312 Second display section 1313 cabinet 1314 Inflection point 1400 Lighting devices 1401 cabinet 1402 Light source 1403 Circuit board 1404 Optical Film 1405 Light Diffusion Section 1500 cars 1501 Taillight 1502 Window 1503 Body 1600 Smart Glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart Glasses 1611 Lens 1612 Control device
Claims
1. An organometallic complex characterized by being represented by the following general formula (1) or general formula (2). 【Chemistry 1】 In general formula (1), A is either a carbon atom or a silicon atom. Each ring B is independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. L is selected from carbon, nitrogen, oxygen, and sulfur atoms. n is either 0 or 1. Ring C is a substituted or unsubstituted heteroaryl ring, and PtL 1 and PtL 2 Each of these is an independent bidentate ligand represented by the following general formula (3). 【Chemistry 2】 In general formula (3), R 1 ~R 3 Each of these is independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.
2. The organometallic complex according to claim 1, characterized by being represented by the following general formula (2). 【Transformation 3】 In general formula (2), A is either a carbon atom or a silicon atom.
3. The organometallic complex according to claim 1, characterized in that n is 0.
4. In general formula (3), R 1 and R 3 Both are alkyl groups, R 2 The organometallic complex according to claim 1, characterized in that is a hydrogen atom.
5. In the general formula (2), ring D is a phenyl group or a naphthalene group, and in the general formula (3), R 1 and R 3 are both alkyl groups, and R 2 is a hydrogen atom. The organometallic complex according to claim 2, characterized in that.
6. The organometallic complex according to claim 1, characterized by being represented by any of the following structural formulas. 【Chemistry 4】
7. A luminescent composition comprising an organometallic complex according to claim 1 and a first organic compound different from the organometallic complex.
8. The luminescent composition according to claim 7, wherein the mass percentage concentration of the organometallic complex relative to the first organic compound is 50% by mass or more and 100% by mass or less.
9. The luminescent composition according to claim 8, wherein the first organic compound is a liquid.
10. An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, The organic light-emitting device is characterized in that the organic compound layer has the organometallic complex described in claim 1.
11. The organic compound layer comprises the organometallic complex and a first organic compound different from the organometallic complex. The organic light-emitting element according to claim 10, characterized in that the lowest excited triplet energy of the first organic compound is equal to or greater than the lowest excited triplet energy of the organometallic complex.
12. The aforementioned organic compound layer is a light-emitting layer, A first charge transport layer is disposed between the first electrode and the light-emitting layer, The device comprises a second charge transport layer disposed between the second electrode and the light-emitting layer, The organic light-emitting element according to claim 11, characterized in that the lowest excited triplet energy of the first charge transport layer is greater than the lowest excited triplet energy of the first organic compound, and the lowest excited triplet energy of the second charge transport layer is greater than the lowest excited triplet energy of the first organic compound.
13. A display device having a plurality of pixels and transistors connected to the plurality of pixels, wherein at least one of the plurality of pixels is an organic light-emitting element according to any one of claims 10 to 12.
14. An imaging device comprising an optical section having a plurality of lenses, an image sensor that receives light that has passed through the optical section, and a display section that displays an image captured by the image sensor, wherein the display section includes an organic light-emitting element as described in any one of claims 10 to 12.
15. An electronic device having a display unit, a housing on which the display unit is provided, and a communication unit provided in the housing for communicating with the outside, wherein the display unit includes an organic light-emitting element as described in any one of claims 10 to 12.
16. A lighting device comprising a light source and a member that transmits light emitted by the light source, wherein the light source includes an organic light-emitting element as described in any one of claims 10 to 12.
17. A mobile body having a light fixture and a body on which the light fixture is provided, wherein the light fixture includes an organic light-emitting element as described in any one of claims 10 to 12.