Organic compound and organic light-emitting element

Abstract

To provide a useful organic compound for constituting an organic light-emitting element having excellent external quantum efficiency.SOLUTION: An organic compound represented by formula (1): A-B (1). In formula (1), A is represented by formula (2), and B is represented by formula (3). In formula (2), one of the X moieties represents a carbon atom bonded to B, and each of the other X moieties represents a nitrogen atom or the like. In formula (3), each of R1 to R3 is a hydrogen atom, an alkyl group or the like, n is 1 or 2, m and p each are an integer of 0-2, and * indicates the bonding position to A.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an organic compound and an organic light-emitting device. [Background technology]

[0002] An organic electroluminescent device (hereinafter sometimes referred to as "organic light-emitting device") is an electronic device having a pair of electrodes, a first electrode and a second electrode, and an organic compound layer disposed between the pair of electrodes. The organic light-emitting device injects electrons and holes from the pair of electrodes into the organic compound layer, thereby activating the light-emitting organic compound in the organic compound layer from a ground state to an excited state, and emitting excess energy as light when the organic compound returns from this excited state to the ground state. The organic light-emitting device is also called an organic electroluminescent device or an organic EL device. In order to improve various properties of organic light-emitting devices, various improvements have been made to the compounds that constitute the organic compound layer. Compound 1 described in Patent Document 1 is a specific carbazole derivative containing a heteroaryl group, and it is disclosed that an organic light-emitting device containing this compound as a constituent component has improved applied voltage and external quantum efficiency.

[0003] [ka] Organic light-emitting devices are mainly manufactured by a vapor deposition method, in which compounds for forming various functional layers such as organic compound layers, inorganic compound layers, and electrodes are heated and vapor-deposited onto a substrate under high vacuum. Meanwhile, in recent years, printing methods have also been considered from the perspectives of material utilization efficiency and manufacturing costs. Patent Document 2 describes a compound in which an oligophenylene structure linked in a linear chain at meta positions is bonded to a compound that forms an organic compound layer by a printing method, and discloses that this improves solubility in organic solvents. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2014 / 157574 [Patent Document 2] Japanese Patent Application Laid-Open No. 2016-88927 Summary of the Invention [Problem to be solved by the invention]

[0005] The present inventors investigated various properties of the compounds described in Patent Documents 1 and 2. As a result, it was found that the external quantum efficiency of Compound 1 described in Patent Document 1 has not yet reached a satisfactory level. In addition, it was found that the compound described in Patent Document 2 has a feature of being soluble in organic solvents, but has a problem with its external quantum efficiency. Therefore, an object of the present invention is to provide an organic compound useful for constructing an organic light-emitting device having excellent external quantum efficiency. Another object of the present invention is to provide an organic compound having excellent solubility in organic solvents. [Means for solving the problem]

[0006] The organic compound of the present invention is characterized by being represented by the following general formula (1). AB (1) (In general formula (1), A is represented by the following general formula (2), and B is represented by the following general formula (3).)

[0007] [ka] (In general formula (2), one of X's is a carbon atom bonded to B, and the other X's are each independently CR or a nitrogen atom. Each R is independently selected from the group consisting of 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group. Adjacent R's may be bonded to each other to form a ring.)

[0008] [ka] (In general formula (3), R1 to R3 are each independently selected from the group consisting of 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group. n is 1 or 2, and m and p are each an integer of 0 or more and 2 or less. * indicates the bonding position to A. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide an organic compound useful as a charge transport material for an organic light-emitting device having excellent external quantum efficiency, and also to provide an organic compound having excellent solubility in organic solvents. [Brief explanation of the drawings]

[0010] [Figure 1]1A is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention, and FIG. 1B is a schematic cross-sectional view showing an example of a display device using an organic light-emitting element according to one embodiment of the present invention. [Figure 2] 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. [Figure 3] 1A is a schematic diagram illustrating an example of an imaging device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of an electronic device according to an embodiment of the present invention. [Figure 4] 1A is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of a foldable display device. [Figure 5] 1A is a schematic diagram showing an example of an illumination device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing an example of a moving body having a vehicle lamp according to an embodiment of the present invention. [Figure 6] 1A is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. [Figure 7] 1A is a schematic diagram illustrating an example of an image forming apparatus according to an embodiment of the present invention, and FIGS. 1B and 1C are schematic diagrams illustrating an example of an exposure light source of the image forming apparatus according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention will be described in further detail below with reference to preferred embodiments. The present invention is not limited to the following description, and it will be readily understood by those skilled in the art that various changes can be made in form and detail without departing from the spirit and scope of the present invention. In other words, the present invention should not be interpreted as being limited by the following description.

[0012] As a result of intensive research, the present inventors have found that although a unit represented by the following general formula (2) exhibits excellent electron transport ability, a compound containing only this unit reduces the external quantum efficiency of an organic light-emitting device due to the formation of trap sites caused by crystallization of the organic thin film. On the other hand, the present inventors have found that a compound in which a specific oligophenylene skeleton, i.e., a unit represented by the following general formula (3), is introduced into the unit represented by general formula (2), particularly a compound in which the unit is introduced at a specific site, improves the external quantum efficiency.

[0013] The compound according to the present invention is represented by the following general formula (1), and is characterized by containing a unit represented by general formula (2) and a unit represented by general formula (3), and preferably has the unit represented by general formula (3) at a specific position. It is presumed that having such a skeleton not only can suppress the formation of trap sites due to crystallization of an organic thin film, but also that bonding to a specific position can control molecular orientation and improve the external quantum efficiency of an organic light-emitting device.

[0014] ≪Organic compounds≫ The organic compound of this embodiment is represented by the following general formula (1). AB (1)

[0015] In the general formula (1), A is represented by the following general formula (2).

[0016] [ka]

[0017] [X] In general formula (2), one of X is a carbon atom bonded to B, and the others are each independently CR or a nitrogen atom. The others of X are preferably CR.

[0018] Each R is independently selected from the group consisting of 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group. Adjacent Rs may be bonded to form a ring.

[0019] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc. Among these, fluorine atoms are preferred from the viewpoint of thermal stability.

[0020] Examples of the alkyl group include linear or branched alkyl groups having from 1 to 30 carbon atoms, preferably from 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, and an n-hexyl group.

[0021] Examples of the cycloalkyl group include monocyclic or polycyclic cycloalkyl groups having from 3 to 12 carbon atoms, preferably from 3 to 6 carbon atoms. Specific examples of the cycloalkyl group include a cyclopropyl group and a cyclohexyl group.

[0022] Examples of the alkoxy group include an alkoxy group having from 1 to 20 carbon atoms, preferably from 1 to 6 carbon atoms. Specific examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, and a 2-ethyl-octyloxy group.

[0023] The aryl group may be an aryl group having from 6 to 30 carbon atoms, and may be a single ring or a fused ring. Specific examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, a phenanthrenyl group, and an anthracenyl group.

[0024] Examples of heteroaryl groups include heteroaryl groups having 3 to 15 atoms constituting the ring, and may be a single ring or a condensed ring. Examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and germanium atoms, and may contain multiple atoms thereof. Specific examples of heteroaryl groups include pyridyl groups, pyrimidyl groups, pyrazyl groups, triazyl groups, benzofuranyl groups, benzothiophenyl groups, dibenzoyl groups, dibenzothienyl groups, oxazolyl groups, oxadiazolyl groups, thiazolyl groups, thiadiazolyl groups, carbazolyl groups, acridinyl groups, and phenanthrolyl groups.

[0025] The aryloxy group includes an aryloxy group in which the carbon number of the aryl moiety is from 6 to 30. Specific examples of the aryloxy group include a phenoxy group and a naphthoxy group.

[0026] Examples of heteroaryloxy groups include heteroaryloxy groups having 3 to 15 atoms constituting the ring of the heteroaryl moiety, and the heteroaryloxy group may be a monocyclic or fused ring. Examples of heteroatoms include the same heteroatoms as those of heteroaryl groups. Specific examples of heteroaryloxy groups include pyridyloxy groups, pyrimidyloxy groups, pyrazyloxy groups, triazyloxy groups, benzofuryloxy groups, dibenzofuryloxy groups, benzothienyloxy groups, dibenzothienyloxy groups, pyryloxy groups, indolyloxy groups, and N-methylcarbazolyloxy groups.

[0027] The silyl group is preferably a group in which an alkyl group, an aryl group, or an alkoxy group is substituted on a silicon atom. Examples of the silyl group include a trialkylsilyl group, a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. Among these, a silyl group substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms is preferred. Specific examples include a trimethylsilyl group, a tert-butyldimethylsilyl group, a triisopropylsilyl group, and a tert-butyldiphenylsilyl group.

[0028] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having carbon atoms of 2 to 20. Specific examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, and a hexyloxycarbonyl group.

[0029] Examples of the acyl group include acyl groups having carbon atoms of 1 to 20. Specific examples of the acyl group include a formyl group, an acetyl group, a propionyl group, and a benzoyl group.

[0030] Examples of the substituent that may be possessed by the alkyl group, cycloalkyl group, alkoxy group, aryl group, heteroaryl group, aryloxy group, heteroaryloxy group, silyl group, alkoxycarbonyl group, and acyl group include a deuterium atom, a halogen atom, an alkyl group, cycloalkyl group, alkoxy group, aryl group, heteroaryl group, aryloxy group, heteroaryloxy group, silyl group, alkoxycarbonyl group, acyl group, and cyano group. Specific examples of the halogen atom, alkyl group, cycloalkyl group, alkoxy group, aryl group, heteroaryl group, aryloxy group, heteroaryloxy group, silyl group, alkoxycarbonyl group, and acyl group that may be possessed by the group include the same as those described for each group above.

[0031] A is preferably represented by the following general formula (4), more preferably represented by the following general formula (5) or (5a), and even more preferably represented by the following general formula (7).

[0032] [ka] In general formula (4), * indicates the bonding position to B.

[0033] [ka] In the general formula (5), X is CR. * indicates the bonding position to B.

[0034] In the general formula (5a), X is CR. * indicates the bonding position to B.

[0035] [Y] In general formula (5a), Y is an oxygen atom, a sulfur atom, N—R′, or C—R″R′″. In particular, when Y is an oxygen atom or a sulfur atom, electron mobility is increased, and the effects of this embodiment can be more effectively achieved.

[0036] R', R'', and R''' are each independently selected from the group consisting of a hydrogen atom, a deuterium 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group.

[0037] Examples of the alkyl group, cycloalkyl group, alkoxy group, aryl group, heteroaryl group, aryloxy group, heteroaryloxy group, silyl group, alkoxycarbonyl group, and acyl group include the same groups as those described above for X.

[0038] [ka] In general formula (7), * indicates the bonding position to B.

[0039] In general formula (1), B is represented by the following general formula (3): In general formula (3), * indicates the bonding position to A.

[0040] [ka]

[0041] [R1 to R3] In general formula (3), R1 to R3 are each independently selected from the group consisting of 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group.

[0042] Examples of the halogen atom, alkyl group, cycloalkyl group, alkoxy group, aryl group, heteroaryl group, aryloxy group, heteroaryloxy group, silyl group, alkoxycarbonyl group, and acyl group include the same groups as those described above for X.

[0043] Examples of the substituent that the alkyl group, cycloalkyl group, alkoxy group, aryl group, heteroaryl group, aryloxy group, heteroaryloxy group, silyl group, alkoxycarbonyl group, and acyl group may have include the same as those described above for X.

[0044] [n,m,p] n is 1 or 2, and m and p are each an integer of 0 or more and 2 or less. By setting n, m, and p within these ranges, the organic compound of this embodiment is densely packed in the organic compound layer, sufficient charge transport ability is maintained, and external quantum efficiency can be increased. To achieve even higher external quantum efficiency, m is more preferably 1 or 2. The sum of m and p may be an integer of 1 or more, in which case m may be an integer of 0 or more and p may be an integer of 1 or more, or m may be an integer of 1 or more and p may be an integer of 0 or more.

[0045] B is preferably represented by the following general formula (6).

[0046] [ka] In the general formula (6), the sum of m and p is an integer of 1 or more.

[0047] <Example> Specific examples of compounds are shown below. Of course, the present invention is not limited to the following specific examples as long as they are included in the definition of general formula (1). Among the following exemplary compounds, exemplary compounds 55 to 57 are particularly preferred.

[0048] [ka]

[0049] [ka]

[0050] [ka] TIFF2025141799000013.tif49157

[0051] <Synthesis method> The organic compound of this embodiment can be synthesized based on a known method. Taking the example of Exemplary Compound 5 as an example, an example of the synthesis scheme is shown below.

[0052] [ka]

[0053] [ka]

[0054] <Organic light-emitting element (organic electroluminescent element)> The organic light-emitting device according to this embodiment includes 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 device according to this embodiment, the organic compound layer may be a single layer or a laminate of multiple layers, as long as it includes a light-emitting layer. The pair of electrodes may be an anode and a cathode.

[0055] When the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have an emitting layer. In addition to the emitting layer, the organic compound layer may 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. The emitting layer may be a single layer or a laminate consisting of multiple layers. The hole transport layer and the electron transport layer are also called charge transport layers.

[0056] In the organic light-emitting device of this embodiment, the organic compound of this embodiment is contained in at least one of the organic compound layers. The organic compound of this embodiment is preferably contained in the light-emitting layer. The transport layers between the first electrode and the light-emitting layer can be collectively referred to as the first charge transport layer. The transport layers between the second electrode and the light-emitting layer can be collectively referred to as the second charge transport layer. That is, the light-emitting layer can be said to be in contact with the first charge transport layer and the second charge transport layer. The lowest excited triplet energy of the layer of the first charge transport layer that is in contact with the first electrode is preferably higher than the lowest excited triplet energy of the organic compound of this embodiment. Furthermore, the lowest excited triplet energy of the layer of the second charge transport layer that is in contact with the second electrode is preferably higher than the lowest excited triplet energy of the organic compound of this embodiment. The lowest excited triplet energy of the charge transport layer can be estimated by the lowest excited triplet energy of the constituent materials of that layer. When the charge transport layer is composed of multiple materials, it may be the lowest excited triplet energy of the compound with the largest mass ratio.

[0057] When the organic compound of this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer consisting solely of the organic compound of this embodiment, or may be a layer containing, in addition to the organic compound of this embodiment, an organometallic complex and another organic compound. The lowest excited triplet energy of the organic compound of this embodiment is preferably equal to or greater than the lowest excited triplet energy of the organometallic complex, and more preferably greater than the lowest excited triplet energy of the organometallic complex. The lowest excited triplet energy of the other organic compound may be equal to or greater than the lowest excited triplet energy of the organometallic complex but less than the lowest excited triplet energy of the organic compound of this embodiment. When the light-emitting layer is a layer containing the organic compound of this embodiment, the organometallic complex, and another organic compound, the organic compound of this embodiment may serve as a host for the light-emitting layer. The organometallic complex may serve as a guest or dopant. The other organic compound may serve as an assist material. The host is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. The guest or dopant is the compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and is responsible for the primary emission of light. The assist material is a compound that has a smaller mass ratio than the host among the compounds that make up the light-emitting layer and assists the guest in emitting light. The assist material is also called the second host.

[0058] When an organometallic complex is used as a guest in the light-emitting layer, the concentration of the guest is preferably 0.01% by mass to 20% by mass, more preferably 5% by mass to 10% by mass, based on the mass of the host.

[0059] The present inventors have conducted various studies and found that high efficiency can be achieved when the organic compound according to this embodiment is used as a host for the light-emitting layer. This light-emitting layer may be a single layer or multiple layers, and it is also possible to mix the light-emitting color of this embodiment with that of the other light-emitting layers by including a light-emitting material having another light-emitting color. "Multiple layers" refers to 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, the white color may be achieved by emitting red, blue, and green light from each light-emitting layer, or by combining complementary light-emitting colors.

[0060] The organic compound according to this embodiment can also be used as a constituent material for organic compound layers other than the light-emitting layer that constitutes the organic light-emitting device, specifically, as a constituent material for an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc.

[0061] <Other compounds> When manufacturing the organic light-emitting device according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may be used together as needed. Examples of these compounds are listed below.

[0062] As the hole injection / transport material, a material with high hole mobility is preferred, facilitating the injection of holes from the anode and transporting the injected holes to the light-emitting layer. Furthermore, a material with a high glass transition temperature is 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 injection / 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. Furthermore, the above-mentioned hole injection / transport materials are also suitable for use in electron blocking layers. Specific examples of compounds that can be used as hole injection / transport materials are listed below, but the present invention is not limited to these.

[0063] [ka]

[0064] [ka]

[0065] The organometallic complex primarily involved in the light-emitting function is a compound capable of emitting light from a triplet excited state. While there are no particular limitations on the organometallic complex as long as it emits light from a triplet excited state, it is preferably an organometallic complex containing at least one metal selected from iridium, platinum, osmium, gold, copper, rhenium, and ruthenium and a ligand. The ligand preferably has an orthometal bond. Metal complexes containing a metal atom selected from iridium, osmium, and platinum are preferred in terms of high phosphorescence quantum yield and further improving the external quantum efficiency of the light-emitting device. Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are more preferred, with orthometallated iridium complexes being even more preferred. Specific examples of compounds usable as organometallic complexes are listed below, but of course, the present invention is not limited to these.

[0066] [ka]

[0067] Examples of the assist material contained in the light-emitting layer include aromatic hydrocarbon compounds or derivatives thereof, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, triazine derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, organic beryllium complexes, polymers such as polyphenylene derivatives, polyphenylenevinylene derivatives, polyfluorene derivatives, and polyvinylcarbazole derivatives, as well as copolymers or mixtures thereof. Specific examples of compounds used as assist materials contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0068] [ka]

[0069] [ka]

[0070] The electron transport material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected taking into consideration the balance with the hole mobility of the hole transport material. Examples of materials having electron transport properties include oxadiazole derivatives, oxazole 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 transport materials are also suitable for use in hole-blocking layers. Specific examples of compounds used as electron transport materials are shown below, but of course, the present invention is not limited to these.

[0071] [ka]

[0072] The electron injection material can be selected from those that allow easy electron injection from the cathode, taking into consideration the balance with hole injection properties, etc. Organic compounds include n-type dopants and reducing dopants. Examples include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives.

[0073] <Configuration of organic light-emitting element> The organic light-emitting element is provided by forming a first electrode, an organic compound layer, and a second electrode on a substrate. An insulating layer may be provided on the substrate. A protective layer, a color filter, a microlens, etc. may be provided on the second electrode. When a color filter is provided, a planarizing layer may be provided between the protective layer. The planarizing layer may be made of acrylic resin, etc. The same applies when a planarizing layer is provided between the color filter and the microlens. Either the first electrode or the second electrode may be an anode, and the other may be a cathode.

[0074] [substrate] Examples of the substrate include quartz, glass, a silicon wafer, a resin, and a metal. Furthermore, the substrate may be provided with a switching element such as a transistor and wiring, and an insulating layer thereon. Any material can be used for the insulating layer, as long as it allows for the formation of a contact hole so that wiring can be formed between the first electrode and the insulating layer, and ensures insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0075] [electrode] A pair of electrodes can be used. The pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0076] The anode material should have as high a work function as possible. Examples include simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures containing these metals, alloys of these metals, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and zinc indium oxide. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0077] These electrode materials may be used alone or in combination of two or more. The anode may be composed of one layer or multiple layers.

[0078] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without functioning as an electrode. When used as a transparent electrode, transparent conductive oxide layers such as indium tin oxide (ITO) and indium zinc oxide can be used, but are not limited to these. Photolithography techniques can be used to form the electrode.

[0079] On the other hand, materials with a low work function are preferred for the cathode. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and metals such as aluminum, titanium, manganese, silver, lead, and chromium, as well as mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, and zinc-silver can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials can be used alone or in combination. The cathode can have either a single-layer or multi-layer structure. Among these, silver is preferred, and a silver alloy is even more preferred to reduce silver aggregation. The alloy ratio is not critical as long as silver aggregation can be reduced. For example, the silver:other metal ratio can be 1:1, 3:1, or the like.

[0080] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but DC and AC sputtering methods are more preferred because they provide good film coverage and make it easier to reduce resistance.

[0081] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. When multiple layers are included, they may be called hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer depending on their functions. The organic compound layer is mainly composed of organic compounds but may also contain inorganic atoms or inorganic compounds. For example, the organic compound layer may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, or the like. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0082] The thickness of each layer in the organic light-emitting device is preferably 1 nm to 10 μm in general, and particularly the thickness of the light-emitting layer of the organic compound layer is preferably 10 nm to 100 nm to obtain effective light-emitting characteristics.

[0083] [Protective layer] A protective layer may be provided on the second electrode. For example, by adhering glass with a moisture absorbent on the second electrode, the infiltration of water and other contaminants into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the infiltration of water and other contaminants into the organic compound layer. For example, after forming the second electrode, the second electrode may be transferred to another chamber without breaking the vacuum, and a 2 μm-thick silicon nitride film may be formed by CVD to serve as a protective layer. A protective layer may be provided using atomic layer deposition (ALD) after the CVD film formation. The material of the film formed by ALD is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed on the film formed by ALD by CVD. The film formed by ALD may have a thickness smaller than that of the film formed by CVD. Specifically, the thickness may be 50% or less, or even 10% or less.

[0084] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on a separate substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using photolithography technology. The color filter may be made of a polymer.

[0085] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing the unevenness of the underlying layer. It may also be called a material resin layer without limiting its purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but a high molecular weight is preferred.

[0086] The planarizing layer may be provided above or below the color filter, and may be made of the same or different materials, such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0087] [Microlens] The organic light-emitting element may have an optical component such as a microlens on its light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be intended to increase the amount of light extracted from the organic light-emitting element and control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be determined in the same way in any cross-sectional view. In other words, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the semicircle is the vertex of the microlens.

[0088] It is also possible to define the midpoint of a microlens. In the cross section of the microlens, a line segment is imagined from the point where an arc shape ends to the point where another arc shape ends, and the midpoint of this line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0089] [Counter substrate] An opposing substrate may be provided on the planarization layer. The opposing substrate is called an opposing substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the opposing substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is defined as a first substrate, the opposing substrate may be a second substrate.

[0090] [Pixel circuit] An organic light-emitting device having an organic light-emitting element may have a pixel circuit connected to the organic light-emitting element. The pixel circuit may be an active matrix type that controls the emission of the first light-emitting element and the second light-emitting element independently. The active matrix type circuit may be voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission brightness of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0091] The 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 a transistor constituting the pixel circuit may be smaller than the mobility of a transistor constituting the display control circuit. The slope of the current-voltage characteristics of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistor constituting the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics. The transistor constituting the pixel circuit is a transistor connected to a light-emitting element, such as a first light-emitting element.

[0092] [Pixels] An organic light emitting device having an organic light emitting element may have a plurality of pixels, each of which has sub-pixels that emit different colors, for example, RGB colors.

[0093] A pixel emits light from an area called a pixel aperture. This area is the same as the first area. The pixel aperture may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc. The distance between subpixels may be 10 μm or less, more specifically, it may be 8 μm, 7.4 μm, or 6.4 μm.

[0094] The pixels may be arranged in a known manner in a plan view. For example, they may be in a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in a plan view may be any known shape. For example, they may be rectangular, quadrilaterals such as diamonds, or hexagons. Of course, a shape that is close to a rectangle, rather than an exact shape, is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0095] <Luminescent composition> The luminescent composition of this embodiment contains the organic compound of this embodiment and an organometallic complex. The concentration of the organometallic complex is preferably 0.01% by mass or more and 20% by mass or less, and more preferably 5% by mass or more and 10% by mass or less, relative to the mass of the organic compound of this embodiment. The luminescent composition may contain various additives, such as a charge transport material, a resin, a plasticizer, an antioxidant, and an ultraviolet absorber, as needed. It is particularly preferable to contain a resin or a charge transport material (e.g., an electron transport material). The resin is preferably a binder resin. Specific 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 a copolymer, and one or more types of resins may be used. Known materials may be used as the electron transport material. Examples of the electron transporting material include 1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl]benzene. Commercially available electron transporting materials (e.g., trade name "OXD-7" manufactured by Lumnescence Technology) can also be used. The content (ppm) of the electron transporting material in the luminescent composition is preferably 10 ppm or more and 5,000 ppm or less based on the total mass of the luminescent composition.

[0096] The luminescent composition may also be in a liquid state. To obtain a liquid luminescent composition, an organic solvent is added. The organic solvent is not particularly limited as long as it can dissolve or disperse the organic compound of the present embodiment. In particular, it is preferable to use an organic solvent having a boiling point of 70°C or higher and 300°C or lower at 1 atmosphere. The content of the organic solvent in the liquid luminescent composition is preferably 85% by mass or higher and 95% by mass or lower, based on the total mass of the luminescent composition.

[0097] Specific examples of organic solvents include toluene, o-xylene, p-xylene, mesitylene, 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, dimethylimidazolidinone, etc. One or more organic solvents can be used to adjust various properties such as the compatibility of various materials in the luminescent composition, and the viscosity and surface tension of the liquid.

[0098] <Method for manufacturing organic light-emitting element> The method for producing an organic light-emitting device of this embodiment includes a step of applying the light-emitting composition of this embodiment to a substrate. The step of applying the light-emitting composition to the substrate may be a step of applying the light-emitting composition to the substrate by a coating method or a printing method.

[0099] A method for producing an organic light-emitting device having organic compound layers (such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer) is described below. The organic light-emitting device is produced by a production method including a step of applying a light-emitting composition to a substrate to form an organic compound layer.

[0100] Examples of methods for forming an organic compound layer include dry processes and wet processes. Examples of dry processes include vacuum deposition, ionization deposition, sputtering, and plasma deposition. Examples of wet processes include known coating methods such as spin coating, casting, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, capillary coating, and slit coating, and printing methods such as screen printing, flexographic printing, offset printing, and inkjet printing. Among these, from the viewpoint of achieving both film uniformity in thin film formation with a thickness of several nanometers and large-area pixel formation, vacuum deposition, ionization deposition, spray coating, slit coating, and inkjet methods are preferred. Among these, spray coating, slit coating, and inkjet methods can be used for compounds with high solubility in organic solvents.

[0101] The wet process will now be described in more detail. The wet process is a method in which a liquid luminescent composition is applied to a substrate by a known method, and an organic compound layer is formed by drying the organic solvent. Drying conditions can be appropriately set depending on the constituent materials of the organic compound layer, etc. Drying is preferably carried out in an air or inert gas (nitrogen, argon, etc.) atmosphere. The heating temperature for drying is preferably 100°C or higher and 250°C or lower, more preferably 110°C or higher and 200°C or lower. The heating time for drying is preferably 5 minutes or higher and 60 minutes or lower. The pressure during heating for drying may be either normal pressure (1 atmosphere) or reduced pressure (100 Pa to 0.1 MPa). The various conditions (temperature, pressure, and time) in the drying step may be set so as to remove the organic solvent from the organic compound layer, etc.

[0102] 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 in the luminescent composition is preferably 10.0 to 100.0 times the total mass of the solid components constituting the organic compound layer. Examples of solid components constituting the organic compound layer include the organic compound of this embodiment and organometallic complexes.

[0103] When forming an organic compound layer by applying a liquid luminescent composition to a substrate using an inkjet method, it is preferable to appropriately control the physical properties of the composition. 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 controlling the viscosity within the above range, clogging and ejection failures in the liquid ejection head when ejecting the composition using an inkjet method can be suppressed.

[0104] <<Uses of organic light-emitting devices>> The organic light-emitting device according to this embodiment can be used as a component of a display device or a lighting device, and can also be used as an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, or a light-emitting device having a white light source and a color filter.

[0105] The display device may be an image information processing device having an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., an information processing unit that processes the input information, and displays the input image on a display unit. The display device has a plurality of pixels, at least one of which may have an organic light-emitting element of this embodiment and an active element such as a transistor connected to the organic light-emitting element. In this case, the substrate may be a semiconductor substrate such as silicon, and the transistor may be a MOSFET formed on the substrate. The image display device has an input unit for inputting image information and a display unit for outputting an image, and the display unit has the display device of this embodiment.

[0106] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. The display device may also be used in the display unit of a multifunction printer.

[0107] Next, a display device according to this embodiment will be described with reference to the drawings. Fig. 1 is a cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin-film transistor (TFT).

[0108] FIG. 1(a) is a cross-sectional schematic diagram of an example of a pixel, which is a component of a display device according to this embodiment. The pixel includes subpixels 10. The subpixels are divided into 10R, 10G, and 10B based on their light emission. The emitted colors may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the subpixels may be selectively transmitted or color-converted using a color filter or the like. Each subpixel 10 includes a reflective electrode serving as a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the edges of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode serving as a second electrode 5, a protective layer 6, and a color filter 7.

[0109] A transistor and a capacitor element may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown).

[0110] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edges of the first electrode 2 and is disposed to surround the first electrode 2. The portion where the insulating layer 3 is not disposed is in contact with the organic compound layer 4 and becomes a light-emitting region.

[0111] The organic compound layer 4 includes a hole injection layer 41 , a hole transport layer 42 , a light emitting layer 43 , a hole blocking layer 44 , and an electron transport layer 45 .

[0112] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0113] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is illustrated as being one layer, it may be multiple layers, and each layer may be an inorganic compound layer and an organic compound layer.

[0114] The color filters 7 are divided into 7R, 7G, and 7B depending on their colors. The color filters 7 may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters 7. The color filters 7 may be formed on a protective layer 6. Alternatively, the color filters 7 may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0115] The display device 100 in FIG. 1(b) has an organic light-emitting element 26 and a TFT 18, which is an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided with an insulating layer 12 on top of it. An active element such as the TFT 18 is disposed on the insulating layer 12, and a gate electrode 13 of the active element, a gate insulating film 14, and a semiconductor layer 15 are provided. The TFT 18 has a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. An anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film 19.

[0116] The electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the embodiment shown in Fig. 1(b). In other words, it is sufficient that either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT 18.

[0117] 1(b), the organic compound layer 22 is illustrated as a single layer, but may be a multi-layer organic compound layer 22. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26.

[0118] In the display device 100 of FIG. 1(b), transistors are used as switching elements, but other switching elements such as MIM elements may be used instead.

[0119] The transistors used in the display device 100 of Fig. 1(b) are not limited to thin-film transistors having an active layer on an insulating surface of a substrate, but may also be transistors using a single-crystal silicon wafer. Examples of active layers include single-crystal silicon, amorphous silicon, microcrystalline silicon, and other non-single-crystal silicon, as well as non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0120] The transistors included in the display device 100 of Fig. 1(b) may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the substrate itself, such as a Si substrate, is processed to form the transistors. In other words, having a transistor within a substrate can be seen as the substrate and the transistor being integrally formed.

[0121] The organic light-emitting element according to this embodiment has its emission brightness controlled by a TFT, which is an example of a switching element. By providing multiple organic light-emitting elements on a surface, an image can be displayed based on the emission brightness of each element. Note that the switching element according to this embodiment is not limited to a TFT, and may be a transistor formed from low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also be referred to as "inside the substrate." Whether to provide a transistor in the substrate or to use a TFT is determined by the size of the display unit. For example, for a display size of about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0122] 2 is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may have 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. The touch panel 1003 and the display panel 1005 are connected by flexible printed circuits FPCs 1002 and 1004. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position even if the display device is a portable device.

[0123] The display device according to this embodiment may have color filters having red, green, and blue colors, which may be arranged in a delta arrangement.

[0124] The display device according to the present embodiment may be used as a display unit of a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

[0125] The display device according to this embodiment may be used as a display unit of an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0126] 3A is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may include a display device according to this embodiment. In this case, the display device may display not only an image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject is moving, the possibility that the subject will be blocked by an obstruction, and the like.

[0127] Since the optimum timing for capturing an image is very short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment. This is because the organic light-emitting element has a fast response speed. Display devices using organic light-emitting elements require high display speed, and these devices can be used more preferably than liquid crystal display devices.

[0128] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses, which form an image on an imaging element housed in a housing 1104. The focus of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may also be called a photoelectric conversion device. Instead of sequentially capturing images, the photoelectric conversion device can include an imaging method that detects the difference from the previous image, or a method of cutting out an image from a constantly recorded image, etc.

[0129] FIG. 3(b) is a schematic diagram illustrating an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint to perform unlocking or the like. 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. An image captured by the camera function is displayed on the display unit 1201. Examples of the electronic device 1200 include a smartphone and a laptop computer.

[0130] FIG. 4 is a schematic diagram illustrating an example of a display device according to this embodiment. FIG. 4(a) illustrates a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The display unit 1302 may use a light-emitting element according to this embodiment. The display device 1300 has the frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 4(a). The lower side of the frame 1301 may also serve as the base. The frame 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0131] FIG. 4(b) is a schematic diagram illustrating another example of a display device according to this embodiment. The display device 1310 in FIG. 4(b) is configured to be bendable, 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 include light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single, seamless display unit. The first display unit 1311 and the second display unit 1312 can be separated by the bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may display a single image.

[0132] FIG. 5(a) is a schematic diagram illustrating an example of a lighting device according to this embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may include an organic light-emitting element according to this embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse light from the light source, such as for illumination, and deliver the light over a wide area. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting device. If necessary, a cover may be provided on the outermost surface.

[0133] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white, daylight white, or any other color from blue to red. It may have a dimming circuit for dimming them or a color tuning circuit for tuning the emitted color. The lighting device may have the organic light-emitting element of this embodiment and a power supply circuit connected to it. The power supply circuit is a circuit that converts AC voltage to DC voltage. The lighting device may have an inverter circuit. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device may have a color filter.

[0134] The lighting device according to this embodiment may also include a heat dissipation unit, which dissipates heat from within the device to the outside, and may be made of a material such as a metal with a high specific heat capacity or liquid silicon.

[0135] 5(b) is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has tail lamps, which are an example of lighting fixtures. The automobile 1500 has tail lamps 1501, and may be configured to turn on the tail lamps when braking or the like is performed.

[0136] The tail lamp 1501 may include an organic light-emitting element according to this embodiment. The tail lamp 1501 may include a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0137] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display as long as it is not a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent materials.

[0138] The moving body according to this embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a body and a lighting device provided on the body. The lighting device may emit light to indicate the position of the body. The lighting device has the organic light-emitting element according to this embodiment.

[0139] An application example of the display device of each of the above-described embodiments will be described with reference to Fig. 6. The display device can be applied to a system that can be attached as a wearable device, such as smart glasses, an HMD, or a smart contact lens. An image capturing and displaying device used in such an application example includes an image capturing device capable of photoelectrically converting visible light and a displaying device capable of emitting visible light.

[0140] Fig. 6(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 6(a), glasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or SPAD is provided on the front side of a lens 1601 of the glasses 1600. In addition, a display device according to each of the above-mentioned embodiments is provided on the back side of the lens 1601.

[0141] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display device. The control device 1603 also controls the operations of the image capture device 1602 and the display device. The lens 1601 is formed with an optical system for focusing light onto the image capture device 1602.

[0142] FIG. 6(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 6(b), glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, which is equipped with an imaging device corresponding to the imaging device 1602 in FIG. 6(a) and a display device. A lens 1611 is formed with an optical system for projecting light emitted from the imaging device in the control device 1612 and the display device, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and also controls the operation of the imaging device and the display device.

[0143] The control device 1612 may include a gaze detection unit that detects the wearer's gaze. The gaze detection may use infrared light. The infrared light emitter emits infrared light toward the eyeball of the user gazing at the display image. An imaging unit with a light-receiving element detects the reflected infrared light from the eyeball, thereby obtaining a captured image of the eyeball. A reduction unit that reduces light from the infrared light emitter to the display unit in a planar view reduces degradation of image quality. The user's gaze toward the displayed image is detected from the captured image of the eyeball obtained by capturing infrared light. Any known method can be applied to gaze detection using the captured image of the eyeball. As an example, a gaze detection method based on a Purkinje image formed by reflection of irradiated light on the cornea can be used. More specifically, gaze detection processing based on the pupil-corneal reflex method is performed. Using the pupil-corneal reflex method, a gaze vector representing the orientation (rotation angle) of the eyeball is calculated based on the image of the pupil and the Purkinje image included in the captured image of the eyeball, thereby detecting the user's gaze.

[0144] A display device according to one embodiment of the present invention may include an imaging device having a light receiving element, and may control the display image of the display device based on user line-of-sight information from the imaging device. Specifically, the display device determines a first field of view area where the user gazes and a second field of view area other than the first field of view area based on the line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0145] The display area includes a first display area and a second display area different from the first display area, and a high-priority area is determined from the first display area and the second display area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or 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 areas other than the high-priority area. In other words, the resolution of an area with a relatively low priority may be lowered.

[0146] Note that AI may be used to determine the first field of view area and areas with high priority. The AI ​​may be a model configured to estimate the angle of gaze and the distance to an object in the line of sight from an image of the eyeball, using as training data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI ​​program may be included in the display device, the imaging device, or an external device. If included in an external device, it is transmitted to the display device via communication.

[0147] When display control is performed based on visual recognition detection, the smart glasses can be preferably applied to smart glasses that further include an imaging device for capturing images of the outside world. The smart glasses can display captured external information in real time.

[0148] 7(a) is a schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 includes the organic light-emitting element according to this embodiment. The developing unit 31 includes toner and the like. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0149] 7(b) and 7(c) are diagrams showing an exposure light source 28 and are schematic diagrams illustrating a state in which multiple light-emitting units 36 are arranged on a long substrate. Arrow 37 indicates the direction parallel to the axis of the photoconductor, the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the axis direction about which the photoconductor 27 rotates. This direction can also be referred to as the long axis direction of the photoconductor 27. FIG. 7(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoconductor 27. FIG. 7(c) shows a configuration different from FIG. 7(b), in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are arranged at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged at intervals. In the second column, light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. In other words, multiple light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in FIG. 7(c) can also be described as a grid arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0150] As described above, by using the device using the organic light-emitting element according to this embodiment, it is possible to achieve a display with good image quality and stability even over a long period of time. Furthermore, by using the device using the organic light-emitting element according to this embodiment, it is possible to achieve both good visibility outdoors due to highly efficient and bright light output and power-saving display. [Example]

[0151] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples as long as the gist of the invention is not exceeded. "Parts" and "percent" used to describe the amounts of components are based on mass unless otherwise specified.

[0152] Example 1 (Synthesis of Exemplary Compound 5) <Synthesis of intermediates> [ka]

[0153] 0.49 g (2.0 mmol, 1.0 eq) of starting material 1, 0.76 g (1.1 eq.) of starting material 2, 0.62 g (3.0 eq.) of sodium carbonate, and 0.06 g (0.03 eq.) of tetrakis(triphenylphosphine)palladium(0) were weighed into a 100 mL three-neck round-bottom flask and subjected to vacuum degassing / Ar purging five times. After thorough vacuum degassing and nitrogen purging, 20 mL of toluene, 5.0 mL of ethanol, and 3.0 mL of water were added under a nitrogen atmosphere. The mixture was refluxed and stirred at 74°C for 8 hours, then the heating was stopped and the reaction mixture was allowed to return to room temperature. After three extractions with toluene, the organic solvent layers were combined, anhydrous sodium sulfate was added, and the mixture was allowed to stand for a while. The sodium sulfate was removed by filtration, and the solution was concentrated under reduced pressure. The resulting oil was subjected to silica gel short column chromatography using toluene as the eluent, and the fraction containing the target product was collected and concentrated under reduced pressure. The oil was purified by silica gel column chromatography using heptane-toluene as the eluent, and the fractions containing the intermediate were collected and concentrated under reduced pressure. The identity of the intermediate was confirmed by MALDI-MS (m / z=471.20).

[0154] The structural formulae of starting material 1 and starting material 2 used in the synthesis, the structural formulae of intermediates, yields and identification data are shown in Table 1 (Table 1-1).

[0155] <Synthesis of Exemplary Compound 5> [ka]

[0156] The synthesized intermediate (0.75 g, 1.6 mmol), starting material 3 (0.38 g, 1.0 eq), Pd(dba)2 (7.0 mg, 0.02 eq), NaOt-buthyl acetate (0.23 g, 1.5 eq), and P(t-buthyl acetate)⋅HBF4 (0.037 g, 0.08 eq) were weighed into a 100 mL three-neck round-bottom flask and subjected to vacuum degassing and Ar purging five times. After thorough vacuum degassing and nitrogen purging, 20 mL of p-xylene was added under a nitrogen atmosphere. The mixture was refluxed and stirred at 180 °C for 8 hours, then the heating was stopped and the reaction mixture was allowed to return to room temperature. After three extractions with toluene, the organic solvent layers were combined, anhydrous sodium sulfate was added, and the mixture was allowed to stand for a while. The sodium sulfate was removed by filtration, and the solution was concentrated under reduced pressure. The resulting oil was subjected to silica gel short column chromatography using toluene as the eluent, and the fractions containing the target product were collected and concentrated under reduced pressure. The resulting oil was subjected to silica gel column chromatography using heptane-toluene as the eluent, and the fractions containing the final product were collected and concentrated under reduced pressure. MALDI-MS confirmed that the product was the desired product (m / z=675.27).

[0157] The structural formulae of the intermediates and starting material 3 used in the synthesis, the structural formulae of the final product, the yield and identification data are shown in Table 2 (Table 2-1).

[0158] Example 2 (Synthesis of exemplified compounds and comparative compounds) <Synthesis of intermediates> For the exemplary compounds and comparative compounds shown in Table 1 (Tables 1-1 to 1-4), intermediates were synthesized in the same manner as in Example 1. The structural formulae of starting material 1 and starting material 2 used in the synthesis, the structural formulae of the intermediates, the yields, and identification data are shown in Table 1 (Tables 1-1 to 1-4).

[0159] [Table 1-1]

[0160] [Table 1-2]

[0161] [Table 1-3]

[0162] [Table 1-4]

[0163] <Synthesis of exemplary compounds and comparative compounds> The exemplary compounds and comparative compounds were synthesized in the same manner as in Example 1. The structural formulae of the intermediates and starting material 3 used in the synthesis, the structural formulae of the final products, the yields and identification data are shown in Table 2 (Tables 2-1 to 2-4).

[0164] [Table 2-1]

[0165] [Table 2-2]

[0166] [Table 2-3]

[0167] [Table 2-4]

[0168] Example 3 (Preparation of luminescent composition) The components shown in Table 3 were mixed in the ratios shown below and stirred for 24 hours at 25° C. After that, the mixture was filtered through a filter with a pore size of 0.2 μm to prepare a luminescent composition. Organometallic complex: 0.25 mass percent Host: 4.75 mass percent Organic solvent: 95.0 mass percent

[0169] [Table 3]

[0170] Example 4 (Fabrication and Evaluation of Element) <Fabrication of element 101> An organic electroluminescent device 101 was fabricated by sequentially depositing an anode, a hole injection layer, a light-emitting layer, an electron transport layer, and a cathode on a substrate according to the following procedure.

[0171] The transparent conductive support substrate (ITO substrate) was a glass substrate on which an ITO film was formed as an anode by sputtering to a thickness of 100 nm. The ITO substrate was washed with pure water and then with isopropanol, and subjected to UV-ozone treatment. A hole injection layer was then formed by spin coating under the following film formation conditions. Coating solution: Poly(3,4-ethylenedioxythiophene) polystyrene sulfonate aqueous solution (PEDOT;PSS aqueous solution, manufactured by Aldrich, conductivity 1 × 10 -5 S / cm, compound concentration 2.8% by mass Spin coating conditions: 3,000 rpm, 60 seconds Annealing conditions: 200°C, 1 hour Film thickness: 40nm

[0172] Next, a light-emitting layer was formed by spin coating under the following film forming conditions. Coating liquid: Luminescent composition No. 1 Spin coating conditions: 2,000 rpm, 60 seconds Annealing conditions: 110°C, 10 minutes Film thickness: 45nm

[0173] Finally, an electron transport layer and an electrode layer were formed by vacuum deposition using resistance heating. 2 The film formation conditions were as follows: Vacuum degree: 1×10 -5 Pa Electron transport layer: TPBi (50nm) Metal electrode layer: LiF (0.5nm), Al (90nm)

[0174] Thereafter, in order to prevent deterioration of the element due to absorption of moisture, the element was covered with a protective glass plate in a dry air atmosphere and sealed with an acrylic resin adhesive.

[0175] <Fabrication of Elements 102 to 114, 201, and 202> Devices 102 to 114, 201 and 202 were produced in the same manner as Device 101, except that in forming the light-emitting layer, the coating liquid was changed to the light-emitting composition shown in Table 4.

[0176] <Fabrication of element 115> The device 115 was fabricated by sequentially depositing an anode, a hole injection layer, a light-emitting layer, an electron transport layer, and a cathode on a substrate according to the following procedure.

[0177] A transparent conductive supporting substrate was prepared in the same manner as in the device 101, and a hole injection layer was formed in the same manner as in the device 101.

[0178] Next, a light-emitting layer was formed by vacuum deposition under the following conditions. Vacuum degree: 1×10 -5 Pa Light-emitting layer: organometallic complex D-8: exemplary compound 5 = 5:95 (mass ratio) (45 nm)

[0179] Thereafter, an electron transport layer and an electrode layer were formed and sealed in the same manner as in the device 101.

[0180] <Fabrication of elements 203 and 204> Devices were fabricated in the same manner as Device 115, except that Example Compound 5 in the light-emitting layer was changed to Comparative Compound 1 or Comparative Compound 2, respectively.

[0181] <Evaluation> For each device, the ITO electrode was used as the anode and the Al electrode as the cathode, and the illumination was 300 cd / m 2 The external quantum efficiency was measured at this time, and the ratio to the measurement result of device 201 was calculated. The evaluation results are shown in Table 4.

[0182] [Table 4]

[0183] From the results in Table 4, it was found that the external quantum efficiency of the devices 101 to 114 of the examples was relatively superior to that of the devices 201 and 202 of the comparative examples.

[0184] Furthermore, among the devices 101 to 114 of the examples, the devices 103 to 114, in which A was a compound represented by general formula (4) as a host, were found to have superior external quantum efficiencies. Furthermore, among the devices 103 to 114, the devices 106 to 114, in which A was a compound represented by general formula (5) or (5a) as a host, were found to have superior external quantum efficiencies. Furthermore, among the devices 106 to 114, the devices 110 to 114, in which B was a compound represented by general formula (6) as a host, were found to have superior external quantum efficiencies. Furthermore, among the devices 110 to 114, the devices 112 to 114, in which A was a compound represented by general formula (7) as a host, were found to have superior external quantum efficiencies.

[0185] Furthermore, the evaluation of the external quantum efficiency of the device 115 of the example was found to be relatively superior to that of the devices 203 and 204 of the comparative examples.

[0186] The present invention is not limited to the above-described embodiments, and various changes and modifications can be made without departing from the spirit and scope of the present invention. Therefore, the following claims are appended to apprise the public of the scope of the present invention.

[0187] ≪Included components≫ The disclosure of this embodiment includes the following configuration. (Configuration 1) An organic compound represented by the following general formula (1): AB (1) (In general formula (1), A is represented by general formula (2) and B is represented by general formula (3).) (In general formula (2), one of X's is a carbon atom bonded to B, and the other X's are each independently CR or a nitrogen atom. Each R is independently selected from the group consisting of 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group. Adjacent R's may be bonded to each other to form a ring.) (In general formula (3), R1 to R3 are each independently selected from the group consisting of 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group. n is 1 or 2, and m and p are each an integer of 0 or more and 2 or less. * indicates the bonding position to A. (Configuration 2) The organic compound according to configuration 1, wherein A is represented by general formula (4). (Configuration 3) 3. The organic compound according to claim 2, wherein A is represented by general formula (5) or (5a). (Configuration 4) 4. The organic compound according to any one of structures 1 to 3, wherein B is represented by general formula (6). (Configuration 5) 5. The organic compound according to any one of structures 1 to 4, wherein A is represented by general formula (7). (Configuration 6) 8. The organic compound according to any one of structures 1 to 7, which is at least one of formulas (55) to (57).

[0188] (Configuration 7) A luminescent composition comprising the organic compound according to any one of Configurations 1 to 6 and an organometallic complex. (Configuration 8) 8. The luminescent composition according to configuration 7, wherein the concentration of the organometallic complex relative to the organic compound is 5% by mass or more and 10% by mass or less. (Configuration 9) 9. The luminescent composition according to aspect 7 or 8, further comprising an organic solvent. (Configuration 10) 10. The luminescent composition according to claim 9, wherein the content of the organic solvent is 85% by mass or more and 95% by mass or less, based on the total mass of the luminescent composition.

[0189] (Configuration 11) An organic light-emitting device having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, 7. An organic light-emitting device, wherein at least one of the organic compound layers comprises the organic compound according to any one of the first to sixth aspects. (Configuration 12) the layer containing the organic compound is a light-emitting layer, and the light-emitting layer further contains an organometallic complex; 12. The organic light-emitting device according to claim 11, wherein the lowest excited triplet energy of the organic compound is equal to or higher than the lowest excited triplet energy of the organometallic complex. (Configuration 13) The organic light-emitting device according to Structure 12, further comprising a first charge transport layer between the first electrode and the light-emitting layer, and a second charge transport layer between the second electrode and the light-emitting layer. (Configuration 14) The organic light-emitting element according to Structure 13, wherein the lowest excited triplet energy of the layer of the first charge transport layer in contact with the first electrode is greater than the lowest excited triplet energy of the organic compound, and the lowest excited triplet energy of the layer of the second charge transport layer in contact with the second electrode is greater than the lowest excited triplet energy of the organic compound.

[0190] (Configuration 15) A display device having a plurality of pixels, at least one of the plurality of pixels having an organic light-emitting element according to any one of structures 11 to 14 and a transistor connected to the organic light-emitting element. (Configuration 16) an optical unit having a plurality of lenses, an image pickup element that receives light that has passed through the optical unit, and a display unit that displays an image picked up by the image pickup element; 15. An imaging device, wherein the display section comprises the organic light-emitting element according to any one of the 11 to 14 configurations. (Configuration 17) 15. An electronic device comprising: a display unit having the organic light-emitting element according to any one of configurations 11 to 14; a housing in which the display unit is provided; and a communication unit provided in the housing and communicating with an external device. (Configuration 18) 15. A lighting device comprising: a light source having the organic light-emitting element according to any one of configurations 11 to 14; and a light diffusion section or an optical filter that transmits light emitted by the light source. (Configuration 19) 15. A moving body comprising: a lighting fixture having the organic light-emitting element according to any one of configurations 1 to 14; and a vehicle on which the lighting fixture is provided. (Configuration 20) a photosensitive member and an exposure light source that exposes the photosensitive member; 15. An image forming apparatus, wherein the exposure light source comprises the organic light-emitting element according to any one of the 11 to 14 configurations.

[0191] (Configuration 21) 11. A method for producing an organic light-emitting device, comprising the step of applying the light-emitting composition according to any one of Configurations 7 to 10 to a substrate. (Configuration 22) 22. The method for producing an organic light-emitting element according to claim 21, wherein the step of applying the luminescent composition to the substrate is a step of applying the luminescent composition to the substrate by a coating method or a printing method. (Configuration 23) 23. The method for producing an organic light-emitting element according to claim 22, wherein the coating method is a spin coating method, a casting method, a gravure coating method, a bar coating method, a roll coating method, a wire bar coating method, a dip coating method, a spray coating method, a capillary coating method, a spray coating method, or a slit coater method. (Configuration 24) 24. The method for producing an organic light-emitting element according to claim 22 or 23, wherein the printing method is a screen printing method, a flexographic printing method, an offset printing method, or an inkjet method. [Explanation of symbols]

[0192] 1: interlayer insulating layer, 2: first electrode, 3: insulating layer, 4: organic compound layer, 5: second electrode, 6: protective layer, 7: color filter, 10: subpixel, 11: substrate, 12: insulating layer, 13: gate electrode, 14: gate insulating film, 15: semiconductor layer, 16: drain electrode, 17: source electrode, 18: TFT, 19: insulating film, 20: contact hole, 21: anode, 22: organic compound layer, 23: cathode, 24: first protective layer, 25: second protective layer, 26: organic light-emitting element, 100: display device

Claims

1. An organic compound represented by the following general formula (1): A-B (1) (In general formula (1), A is represented by the following general formula (2), and B is represented by the following general formula (3).) 【Chemical 1】 (In general formula (2), one of X's is a carbon atom bonded to B, and the other X's are each independently C—R or a nitrogen atom. Each R is independently selected from the group consisting of 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group.) Adjacent R's may be bonded to form a ring. 【Chemistry 2】 (In general formula (3), R 1 ~R 3 are each independently selected from the group consisting of 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group. n is 1 or 2, and m and p are each an integer of 0 or more and 2 or less. * indicates the bonding position to A.

2. 2. The organic compound according to claim 1, wherein A is represented by the following general formula (4): 【Chemistry 3】 (In general formula (4), * indicates the bonding position to B.)

3. 3. The organic compound according to claim 2, wherein A is represented by the following general formula (5) or (5a): 【Chemistry 4】 (In general formula (5), X is C—R. In general formula (5a), X is C—R. Y is O, S, NR', or CR''R'''. R', R'', and R''' are each independently selected from the group consisting of a hydrogen atom, a deuterium 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, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyl group, and a cyano group.

4. 4. The organic compound according to claim 1, wherein B is represented by the following general formula (6): 【Chemistry 5】 (In general formula (6), the sum of m and p is an integer of 1 or more.)

5. 4. The organic compound according to claim 1, wherein A is represented by the following general formula (7): 【Chemistry 6】 (In general formula (7), * indicates the bonding position to B.)

6. 4. The organic compound according to claim 1, which is at least one of the following formulae (55) to (57): 【Chemistry 7】

7. A luminescent composition comprising the organic compound according to claim 1 and an organometallic complex.

8. 8. The luminescent composition according to claim 7, wherein the concentration of the organometallic complex relative to the organic compound is 5% by mass or more and 10% by mass or less.

9. 8. The luminescent composition according to claim 7, further comprising an organic solvent.

10. 10. The luminescent composition according to claim 9, wherein the content of the organic solvent is 85% by mass or more and 95% by mass or less based on the total mass of the luminescent composition.

11. An organic light-emitting device having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic compound layers comprises the organic compound according to claim 1 .

12. the layer containing the organic compound is a light-emitting layer, and the light-emitting layer further contains an organometallic complex; The organic light-emitting device according to claim 11, wherein the lowest excited triplet energy of the organic compound is equal to or higher than the lowest excited triplet energy of the organometallic complex.

13. 13. The organic light-emitting element according to claim 12, further comprising a first charge transport layer between the first electrode and the light-emitting layer, and a second charge transport layer between the second electrode and the light-emitting layer.

14. 14. The organic light-emitting element according to claim 13, wherein the lowest excited triplet energy of the layer of the first charge transport layer in contact with the first electrode is greater than the lowest excited triplet energy of the organic compound, and the lowest excited triplet energy of the layer of the second charge transport layer in contact with the second electrode is greater than the lowest excited triplet energy of the organic compound.

15. A display device comprising a plurality of pixels, at least one of the plurality of pixels comprising the organic light-emitting element according to claim 11 and a transistor connected to the organic light-emitting element.

16. an optical unit having a plurality of lenses, an image pickup element that receives light that has passed through the optical unit, and a display unit that displays an image picked up by the image pickup element; An imaging device, wherein the display unit comprises the organic light-emitting element according to claim 11.

17. 12. An electronic device comprising: a display unit having the organic light-emitting element according to claim 11; a housing in which the display unit is provided; and a communication unit provided in the housing for communicating with an external device.

18. 12. A lighting device comprising: a light source having the organic light-emitting element according to claim 11; and a light diffusion section or an optical filter that transmits light emitted by the light source.

19. A moving body comprising: a lighting fixture having the organic light-emitting element according to claim 11; and a vehicle on which the lighting fixture is provided.

20. a photosensitive member and an exposure light source that exposes the photosensitive member; 12. An image forming apparatus, wherein the exposure light source comprises the organic light emitting element according to claim 11.

21. A method for producing an organic light-emitting device, comprising the step of applying the light-emitting composition according to claim 7 to a substrate.

22. 22. The method for producing an organic light-emitting element according to claim 21, wherein the step of applying the light-emitting composition to the substrate is a step of applying the light-emitting composition to the substrate by a coating method or a printing method.

23. 23. The method for manufacturing an organic light-emitting element according to claim 22, wherein the coating method is a spin coating method, a casting method, a gravure coating method, a bar coating method, a roll coating method, a wire bar coating method, a dip coating method, a spray coating method, a capillary coating method, or a slit coater method.

24. The method for manufacturing an organic light-emitting device according to claim 22, wherein the printing method is a screen printing method, a flexographic printing method, an offset printing method, or an inkjet method.

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