Organic compounds and organic light-emitting devices

Abstract

To provide an organic compound with light emission characteristics excellent in sublimability or solubility.SOLUTION: The organic compound is represented by general formula (1): Ip-L1-Ar-L2-FL (1). In general formula (1), Ip is an indenopyrene-containing skeleton, Ar is a heteroaryl group or a spirofluorene-containing skeleton, FL is an indenopyrene skeleton or a skeleton having a structure represented by general formula (2), and L1 and L2 are each independently selected from the group consisting of a direct bond and an arylene group. In general formula (2), X is an oxygen atom, a sulfur atom, a nitrogen atom, or the like.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This invention relates to an organic compound and an organic light-emitting device using the same. [Background technology]

[0002] An organic light-emitting element (hereinafter sometimes referred to as an "organic electroluminescent element" or "organic EL element") is an electronic element having a first electrode, a second electrode, and an organic compound layer placed between these electrodes. By injecting electrons and holes from this pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and when these excitons return to the ground state, the organic EL element emits light.

[0003] Recent advances in organic EL elements are remarkable, including low drive voltage, diverse emission wavelengths, fast response times, and the ability to make light-emitting devices thinner and lighter.

[0004] To improve the performance of light-emitting devices, the development of even higher-performance light-emitting organic compounds is required, and active development efforts are underway.

[0005] Patent Document 1 discloses the following compound A as a material for an organic light-emitting element that has extremely high efficiency, high brightness, and high color purity. [ka] [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] Japanese Patent Publication No. 2010-111620 [Overview of the project] [Problems that the invention aims to solve]

[0007] However, since the linking group connecting two indenopyrenes in Compound A described in Patent Document 1 is a highly planar biphenyl group, the sublimability and solubility of the compound are not sufficient, resulting in low luminescence properties. Therefore, there is room for improvement in the luminescence properties of Compound A described in Patent Document 1.

[0008] The present invention has been made in view of the above problems, and an object thereof is to provide an organic compound having excellent luminescence properties.

Means for Solving the Problems

[0009] The organic compound according to the present invention is characterized by being represented by the general formula (1).

[0010] Ip-L<0000I04>-Ar-L 2 -FL (1) In the general formula (1), Ip represents a skeleton having indenopyrene, Ar represents a substituted or unsubstituted heteroaryl group or a skeleton having spirofluorene, and FL represents an indenopyrene skeleton or a skeleton having a structure represented by the general formula (2). L 1 and L 2 are each independently selected from a direct bond or a substituted or unsubstituted arylene group.

Chemical formula

[0011] In the general formula (^), X represents an oxygen atom, a sulfur atom, a nitrogen atom, CR 1 R 2 or NR 3 and R 1 to R 3 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. [[ID=^7]]

Effects of the Invention

[0012] According to the present invention, it is possible to provide an organic compound with excellent luminescence properties. [Brief explanation of the drawing]

[0013] [Figure 1] (a) A schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention. (b) 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] This is a schematic diagram illustrating an example of a display device according to one embodiment of the present invention. [Figure 3] (a) A schematic diagram showing an example of an imaging device according to one embodiment of the present invention. (b) A schematic diagram showing an example of an electronic device according to one embodiment of the present invention. [Figure 4] (a) A schematic diagram showing an example of a display device according to one embodiment of the present invention. (b) A schematic diagram showing an example of a foldable display device. [Figure 5] (a) A schematic diagram showing an example of a lighting device according to one embodiment of the present invention. (b) A schematic diagram showing an example of an automobile having a vehicle light fixture according to one embodiment of the present invention. [Figure 6] (a) A schematic diagram showing an example of a wearable device according to one embodiment of the present invention. (b) A schematic diagram showing an example of a wearable device according to one embodiment of the present invention, which includes an imaging device. [Figure 7] (a) A schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. (b) A schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. (c) A schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. [Figure 8] (a) Normalized EL spectrum of compound (1). (b) Normalized EL spectra of compound (25), compound (29), and compound A. [Modes for carrying out the invention]

[0014] In this specification, the alkyl group may be an alkyl group having 1 to 20 carbon atoms. Examples include, but are not limited to, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a tert-pentyl group, a 3-methylpentan-3-yl group, a 1-adamantyl group, and a 2-adamantyl group.

[0015] The aryl group may be any aryl group having 6 to 20 carbon atoms. Examples include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, anthranyl, perilenyl, chrysenyl, and fluoranthenyl groups.

[0016] The heteroaryl group may be any heteroaryl group having 3 to 24 carbon atoms. Examples include, but are not limited to, pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, and phenanthrolyl groups.

[0017] Examples of substituents that the alkyl, aryl, and heteroaryl groups mentioned above may further have include, but are not limited to, alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl groups; aralkyl groups such as benzyl groups; aryl groups such as phenyl and biphenyl groups; heteroaryl groups such as pyridyl and pyrrolyl groups; amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino groups; alkoxy groups such as methoxy, ethoxy, and propoxy groups; aryloxy groups such as phenoxy groups; halogen atoms such as fluorine, chlorine, bromine, and iodine; deuterium atoms; and cyano groups.

[0018] (1)Organic compounds First, let me explain the organic compounds according to the present invention.

[0019] The organic compound according to the present invention is characterized by being represented by general formula (1). Ip-L 1 -Ar-L 2 -FL (1)

[0020] In general formula (1), Ip is a skeleton having an indenopyrene skeleton. Ip may have a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group as substituents. Specifically, it is preferable to have an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or a tert-butyl group. This is because these substituents are bulkier than hydrogen atoms, and therefore the aggregation of molecules can be further suppressed by having these substituents. Furthermore, among indenopyrene skeletons, it is particularly preferable that Ip has a 7H-indeno[1,2-a]pyrene skeleton. Among indenopyrene skeletons, the 7H-indeno[1,2-a]pyrene skeleton has a particularly high oscillator intensity, and therefore a higher luminescence efficiency can be obtained. Also, when Ip is a 7H-indeno[1,2-a]pyrene skeleton, it is preferable that the substituent is located at the 2 position of the skeleton. Furthermore, when Ip is a 7H-indeno[1,2-a]pyrene skeleton, it is preferable that it is bonded to Ar at position 9 of 7H-indeno[1,2-a]pyrene. This is because bonding to Ar at position 9 of 7H-indeno[1,2-a]pyrene (the numbers in the structural formula below indicate the substitution position of 7H-indeno[1,2-a]pyrene) improves the oscillator strength of the skeleton and thus improves the luminescence efficiency. [ka]

[0021] In general formula (1), Ar is a skeleton having a substituted or unsubstituted heteroaryl group or a spirofluorene. Ar may further have a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Specifically, it is preferable to have an alkyl group having 1 to 4 carbon atoms, and more preferably to have a tert-butyl group.

[0022] When Ar is a substituted or unsubstituted heteroaryl group, it is preferable that the heteroaryl group has a nitrogen atom as a heteroatom, and more preferably has at least one skeleton from among the pyridine skeleton, pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton, triazine skeleton, quinoline skeleton, isoquinoline skeleton, and naphthyridine skeleton, and more preferably has at least one skeleton from among the pyridine skeleton, pyrimidine skeleton, and triazine skeleton. This is because the pyridine skeleton, pyrimidine skeleton, and triazine skeleton have excellent chemical stability even at high temperatures. Furthermore, these skeletons are preferred from the viewpoint of emitting blue light with excellent color purity because their conjugation length is particularly short. In addition, when Ar is a pyridine skeleton, pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton, or triazine skeleton, it is preferable that it is bonded to Ip and FL at the meta position of the skeleton. This is because bonding to Ip and FL at the meta position of Ar shortens the conjugation length, thus enabling the emission of blue light with excellent color purity.

[0023] Furthermore, when Ar has a spirofluorene skeleton, it is preferable that Ar has a spirobifluorene skeleton. Specifically, examples include 9,9'-spirobifluorene, spiro[7H-benzo[c]fluorene-7,9'-[9H]fluorene], spiro[9H-fluorene-9,9'-[9H]indeno[2,1-c]phenanthrene], spiro[13H-dibenzo[a,i]fluorene-13,9'-[9H]fluorene], spiro[4H-cyclopenta[def]phenanthrene-4,9'-[9H]fluorene], and spiro[fluorene-9,7'-fluoreno[4,3-b]benzofuran]. Among these, the 9,9'-spirobifluorene skeleton is particularly preferred. This is because the 9,9'-spirobifluorene skeleton has a particularly short conjugation length, allowing it to emit blue light with excellent color purity. Furthermore, when Ar is the 9,9'-spirobifluorene skeleton, it is preferable for it to bond with Ip and FL at the 2, 2', 7, or 7' position of 9,9'-spirobifluorene (the numbers in the structural formula on the left below indicate the substitution position of 9,9'-spirobifluorene). This is because the binding of fluorene to Ip and FL at the 2 or 7 position (the numbers in the structural formula on the right below indicate the substitution position of fluorene) improves oscillator strength and thus improves luminescence efficiency. [ka]

[0024] In general formula (1), FL has an indenopyrene skeleton or a skeleton having a structure represented by general formula (2). In particular, it is preferable to have an indenopyrene skeleton, a fluorene skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, or a carbazole skeleton. This is because the indenopyrene skeleton and the fluorene skeleton have high oscillator intensity and excellent luminescence efficiency. Furthermore, when a dibenzofuran skeleton, a dibenzothiophene skeleton, or a carbazole skeleton is present, the abundant lone pairs of electrons on the oxygen, sulfur, and nitrogen atoms contained in the skeleton can enhance charge transport. Therefore, it is preferable as a compound that allows for easy adjustment of the carrier balance. In particular, from the viewpoint of improving luminescence efficiency, it is even more preferable to have an indenopyrene skeleton or a fluorene skeleton, and it is especially preferable to have a 7H-indeno[1,2-a]pyrene skeleton.

[0025] Furthermore, FL may have a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group as substituents. Specifically, the substituent is preferably a C1 to C4 alkyl group, and more preferably a tert-butyl group. [ka]

[0026] In general formula (2), X is an oxygen atom, a sulfur atom, a nitrogen atom, and CR. 1 R 2 , or NR 3 Represents R 1 ~R 3 R is independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 ~R 3The substituent is preferably an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms, and more preferably a methyl group. This is because the substituent is bulkier than a hydrogen atom, and therefore its presence can suppress molecular aggregation.

[0027] In general formula (1), L 1 and L 2 L is independently selected from directly bonded, substituted, or unsubstituted arylene groups. 1 and L 2 It is preferable that the direct bond or the phenylene group be selected independently.

[0028] Furthermore, when the organic compound according to the present invention contains a deuterium atom, it exhibits excellent durability. As a result, when the organic compound according to the present invention is used in an organic light-emitting device, it is possible to provide an organic light-emitting device with excellent device lifespan.

[0029] Organic compounds represented by general formula (1) have the following characteristics. (1-1) The presence of a substituted or unsubstituted heteroaryl group of Ar results in excellent sublimation properties. (1-2) The Ar group has a spirofluorene skeleton, which gives it excellent solubility.

[0030] The following describes these features.

[0031] (1-1) The presence of a substituted or unsubstituted heteroaryl group of Ar results in excellent sublimation properties.

[0032] As a result of diligent research, the inventors of the present invention have found that the organic compound according to the present invention exhibits excellent sublimation properties when Ar is a substituted or unsubstituted heteroaryl group.

[0033] Compound A, described in Patent Document 1, uses a biphenylene group as a linking group to connect two indenopylene skeletons. The biphenylene group is an aromatic compound composed of hydrocarbons and has a highly planar structure, making it easy to perform intermolecular stacking. Therefore, it tends to have a high sublimation temperature.

[0034] On the other hand, organic compounds represented by general formula (1) are heteroaryl groups in which Ar is substituted or unsubstituted. It is thought that intermolecular stacking can be suppressed because the electron density or polarizability of Ar is biased, which weakens intermolecular interactions.

[0035] Based on the above, the organic compound according to the present invention is an organic compound with a low sublimation temperature when Ar is a substituted or unsubstituted heteroaryl group. In other words, it can be said to be an organic compound with excellent sublimation properties.

[0036] (1-2) The Ar group has a spirofluorene skeleton, which gives it excellent solubility.

[0037] As a result of further diligent research, the inventors discovered that the organic compound according to the present invention exhibits excellent solubility because Ar has a spirofluorene-containing skeleton.

[0038] The organic compound represented by general formula (1) has a skeleton in which Ar has a spirofluorene group, and therefore can have higher solubility than compound A which has a biphenylene group.

[0039] Based on the above, organic compounds in which Ar has a spirofluorene skeleton in general formula (1) are organic compounds with excellent solubility.

[0040] Specific examples of organic compounds according to the present invention are shown below. However, the present invention is not limited to these. [ka] [ka]

[0041] Of the example compounds listed above, compounds (1) to (24) are organic compounds in which Ar is a substituted or unsubstituted heteroaryl group. Therefore, they are organic compounds with particularly excellent sublimation properties.

[0042] Of the example compounds listed above, compounds (25) to (48) are organic compounds in which Ar has a spirofluorene skeleton. Therefore, they are organic compounds with particularly excellent solubility.

[0043] (2) Organic light-emitting element Next, the organic light-emitting element of this embodiment will be described. The organic light-emitting element of this embodiment comprises at least a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. The first electrode and the second electrode may be an anode and the other a cathode. In the organic light-emitting element of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, provided that it has a light-emitting layer. If the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the light-emitting layer, 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 light-emitting layer may also be a single layer or a laminate consisting of multiple layers.

[0044] In the organic light-emitting element of this embodiment, at least one layer of the organic compound layer contains the organic compound according to this embodiment. Specifically, the organic compound according to this embodiment is included in any of the above-mentioned light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, hole-exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound according to this embodiment is preferably included in the light-emitting layer.

[0045] In the organic light-emitting element of this embodiment, when the organic compound according to this embodiment is included in the light-emitting layer, the light-emitting layer may consist only of the organic compound according to this embodiment, or it may consist of the organic compound according to this embodiment and other compounds. Here, when the light-emitting layer consists of the organic compound according to this embodiment and other compounds, the organic compound according to this embodiment may be used as a host or a guest in the light-emitting layer. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. The guest is a compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and is responsible for the main light emission. The assist material is a compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and assists the light emission of the guest. The assist material is also called the second host. The host material can also be called the first compound, and the assist material can be called the second compound.

[0046] When the organic compound according to this embodiment is used as a guest in the light-emitting layer, the concentration of the guest is preferably 0.01% by mass or more and 20% by mass or less relative to the entire light-emitting layer, and more preferably 0.01% by mass or more and 5.0% by mass or less.

[0047] The inventors conducted various studies and found that when the organic compound according to this embodiment is used as a host or guest for the light-emitting layer, particularly as a guest for the light-emitting layer, a device exhibiting high efficiency, high brightness, and high durability can be obtained. This light-emitting layer may be a single layer or a multi-layer, and it is also possible to mix it with the blue light emission of this embodiment by including a light-emitting material having another light-emitting color. A multi-layer means a state in which one light-emitting layer and another light-emitting layer are stacked. In this case, the light-emitting color of the organic light-emitting element is not limited to blue. More specifically, it may be white or an intermediate color. In the case of white, the other light-emitting layer emits a color other than blue, i.e., red or green. Furthermore, the film is formed by vapor deposition or coating. Details of this will be explained in detail in the examples described later.

[0048] The organic compound according to this embodiment can be used as a constituent material for organic compound layers other than the light-emitting layer constituting the organic light-emitting element of this embodiment. Specifically, it may be used as a constituent material for electron transport layers, electron injection layers, hole transport layers, hole injection layers, hole blocking layers, etc. In this case, the light-emitting color of the organic light-emitting element is not limited to blue. More specifically, it may be white light or an intermediate color.

[0049] In addition to the organic compounds according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injection compounds or hole-transport compounds, host compounds, luminescent compounds, electron-injection compounds or electron-transport compounds, etc., can be used together as needed. Examples of these compounds are listed below.

[0050] As hole-injection transport materials, materials with high hole mobility are preferred to facilitate hole injection from the anode and to transport the injected holes to the light-emitting layer. Furthermore, materials with a high glass transition temperature are preferred to suppress deterioration of the film quality, such as crystallization, in the organic light-emitting element. Examples of low-molecular-weight and high-molecular-weight materials with hole-injection transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. In addition, the above-mentioned hole-injection transport materials are also suitably used in electron-blocking layers. Alternatively, a mixture of polyethylenedioxythiophene and polystyrene sulfonic acid (PEDOT:PSS), which is commonly used as a hole injection material when manufactured by coating methods, may be used. Specific examples of compounds used as hole-injection transport materials are shown below, but are not limited to these. [ka]

[0051] Among the hole transport materials listed, HT16 to HT18 can reduce the driving voltage when used in the layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2, HT3, HT4, HT5, HT6, HT7, HT10, and HT12 may be used in the organic compound layer adjacent to HT16. Polymer compounds such as hole-transporting polyphenylene vinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives may also be used. In addition, inorganic insulating layers such as SiO2 and SiN, or organosilicon polymers such as siloxanes can also be used. Furthermore, multiple materials may be used in a single organic compound layer.

[0052] Luminescent materials primarily involved in light emission include fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Furthermore, when producing a luminescent layer by coating, polymer compounds with luminescent properties are mainly used. This is because polymer compounds have high amorphous properties, making them less prone to crystallization compared to low molecular weight systems. Specifically, materials used include polymer compounds such as polyphenylenevinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives.

[0053] The following are some specific examples of compounds used as luminescent materials, but of course, they are not the only ones. [ka] [ka]

[0054] When the luminescent material is a hydrocarbon compound, it is preferable because it can reduce the decrease in luminescence efficiency due to excyplex formation and the decrease in color purity due to changes in the emission spectrum of the luminescent material caused by excyplex formation.

[0055] Hydrocarbon compounds are compounds composed only of carbon and hydrogen, and among the example compounds listed above, these include BD7, BD8, GD5 through GD9, and RD1.

[0056] When the luminescent material is a condensed polycyclic material containing a five-membered ring, it is preferable because its ionization potential is high, making it less susceptible to oxidation and resulting in a highly durable device with a long lifespan. Among the example compounds listed above, BD7, BD8, GD5 to GD9, and RD1 are preferred.

[0057] Examples of light-emitting layer hosts or light-emitting assist materials included in the light-emitting layer include aromatic hydrocarbon compounds or their derivatives, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, organoberylium complexes, and organoplatum complexes.

[0058] The following are specific examples of compounds used as luminescent layer hosts or luminescence assist materials contained in the luminescent layer, but of course, they are not limited to these. [ka]

[0059] When the host material is a hydrocarbon compound, the compound of the present invention is more likely to trap electrons and holes, thus greatly improving efficiency, which is preferable. A hydrocarbon compound is a compound composed only of carbon and hydrogen, and among the example compounds above, these are EM1 to EM12 and EM16 to EM27.

[0060] As electron-transporting materials, any material capable of transporting electrons injected from the cathode to the light-emitting layer can be arbitrarily selected, taking into consideration the balance with the hole mobility of the hole-transporting material. Examples of materials with electron-transporting properties include oxadiazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron-transporting materials are also suitably used in the hole-blocking layer.

[0061] The following are specific examples of compounds used as electron transport materials, but of course, they are not the only ones. [ka]

[0062] Electron-injectable materials can be arbitrarily selected from those that allow for easy electron injection from the cathode, taking into consideration the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. Examples include alkali metal compounds such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fluvalene derivatives, and acridine derivatives.

[0063] It can also be used in combination with the electron transport materials mentioned above.

[0064] [Ink composition] Next, the ink composition according to this embodiment will be described.

[0065] The ink composition according to this embodiment contains at least one compound represented by general formula (2).

[0066] Compounds of general formula (2) have good solubility in organic solvents and can therefore be used as ink compositions. Furthermore, by using the ink composition according to this embodiment, it becomes possible to fabricate layers made of the organic compounds constituting the organic light-emitting element according to this embodiment, particularly the light-emitting layer, by a coating method, making it possible to easily produce large-area elements at relatively low cost. Examples of solvents for dissolving the compound represented by general formula (2) include toluene, xylene, mesitylene, dioxane, methylnaphthalene, tetrahydrofuran, diglyme, 1,2-dichlorobenzene, and 1,2-dichloropropane. These solvents can be used individually or in combination of two or more. Among these, it is preferable to use a solvent with a suitable evaporation rate, specifically one with a boiling point of about 70 to 200°C, as it is easier to obtain a thin film with a uniform thickness. In addition, the ink composition according to this embodiment may also contain other additive compounds. Examples of additive compounds include the above-mentioned known light-emitting layer host or light-emitting assist material, hole transport material, light-emitting material, electron transport material, etc.

[0067] The concentration of the compound represented by general formula (2) in the ink composition according to this embodiment is preferably 0.05% by weight or more and 20% by weight or less, and more preferably 0.1% by weight or more and 5% by weight or less, relative to the entire composition.

[0068] The ink composition according to this embodiment can be formed by spin coating, bar coating, slit coating, inkjet, nozzle coating, casting, gravure printing, etc. The organic light-emitting element of the present invention can be used to construct a display device such as a screen by forming the organic light-emitting element of the present invention on electrodes formed in a pixel pattern.

[0069] [Configuration of organic light-emitting element] An organic light-emitting element is provided on a substrate by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode. A protective layer, a color filter, a microlens, etc., may be provided on the second electrode. If a color filter is provided, a planarization layer may be provided between it and the protective layer. The planarization layer can be made of acrylic resin or the like. The same applies when a planarization layer is provided between the color filter and the microlens. Either the first electrode or the second electrode may be the anode and the other the cathode.

[0070] [substrate] Examples of substrates include quartz, glass, silicon wafers, resins, and metals. The substrate may also be equipped with switching elements such as transistors and wiring, and an insulating layer may be provided on top of them. The insulating layer can be made of any material that allows for the formation of contact holes between it and the first electrode, while ensuring insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, and silicon nitride can be used.

[0071] [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 the higher potential is the anode, and the other is the cathode. Alternatively, the electrode that supplies holes to the light-emitting layer can be the anode, and the electrode that supplies electrons can be the cathode.

[0072] For the anode, materials with the largest possible work function are preferable. For example, elemental metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, or mixtures containing these, or alloys combining them, as well as metal oxides such as tin oxide, zinc oxide, indium oxide, tin-indium oxide (ITO), and zinc-indium oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0073] These electrode materials may be used individually or in combination of two or more types. Furthermore, the anode may consist of a single layer or multiple layers.

[0074] When used as a reflective electrode, materials such as chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. It is also possible to use the above materials as a reflective film without serving as an electrode. Furthermore, when used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO) or indium zinc oxide can be used, but are not limited to these. Photolithography can be used to form the electrodes.

[0075] On the other hand, materials with a small work function are preferred for the cathode. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and elemental metals or mixtures containing aluminum, titanium, manganese, silver, lead, and chromium. Alternatively, alloys combining these elemental metals can also 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 may be used individually or in combination of two or more. The cathode may also be 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 important as long as silver aggregation is reduced. For example, the ratio of silver to other metals may be 1:1, 3:1, etc.

[0076] 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 using DC and AC sputtering methods is more preferable because it provides good film coverage and makes it easier to reduce resistance.

[0077] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. If there are multiple layers, they may be called a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on their function. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms and inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be placed between the first electrode and the second electrode, or it may be placed in contact with the first electrode and the second electrode.

[0078] [Protective layer] A protective layer may be provided on the cathode. For example, by bonding glass with a desiccant to the cathode, the intrusion of water and other substances 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 cathode to reduce the intrusion of water and other substances into the organic compound layer. For example, after forming the cathode, it may be transported to another chamber without breaking the vacuum and a silicon nitride film with a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer may also be provided using atomic deposition (ALD) after the film formation by the CVD method. The material of the film formed by the ALD method is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed on the film formed by the ALD method by the CVD method. The film formed by the ALD method may have a thinner film thickness than the film formed by the CVD method. Specifically, it may be 50% or less, or even 10% or less.

[0079] [Color Filter] A color filter may be provided on top of the protective layer. For example, a color filter that takes into account the size of the organic light-emitting element may be provided on a separate substrate and bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer as described above using photolithography technology. The color filter may be made of polymer.

[0080] [Planarization layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer is provided to reduce the unevenness of the layer below. It may also be called a material resin layer without limiting its purpose. The planarizing layer may be composed of an organic compound, which may be low molecular weight or high molecular weight, but high molecular weight is preferred.

[0081] The planarization layer may be provided above or below the color filter, and its constituent materials may be the same or different. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, urea resin, etc.

[0082] [Microlens] An organic light-emitting device may have optical elements such as microlenses on its light-emitting side. Microlenses may be made of acrylic resin, epoxy resin, or the like. Microlenses may be used to increase the amount of light extracted from the organic light-emitting device or to control the direction of the extracted light. Microlenses may have a hemispherical shape. If they have a hemispherical shape, among the tangents tangent to the hemisphere, there is a tangent parallel to the insulating layer, and the point of contact between that tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be similarly determined in any cross-sectional view. That is, among the tangents tangent to the semicircle of the microlens in the cross-sectional view, there is a tangent parallel to the insulating layer, and the point of contact between that tangent and the semicircle is the vertex of the microlens.

[0083] Furthermore, the midpoint of a microlens can also be defined. In the cross-section of a microlens, a line segment can be imagined from the point where one arc ends to the point where another arc ends, and the midpoint of this line segment can be called the midpoint of the microlens. The cross-section used to determine the vertices and midpoints may be a cross-section perpendicular to the insulating layer.

[0084] [Opposite substrate] A counter substrate may be provided on the planarized layer. The counter substrate is called a counter substrate because it is provided in a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. The counter substrate may be the second substrate if the aforementioned substrate is referred to as the first substrate.

[0085] [Formation of an organic compound layer] The organic compound layer (hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light-emitting element according to one embodiment of the present invention is formed by the method shown below.

[0086] The organic compound layer constituting the organic light-emitting element according to one embodiment of the present invention can be formed using a dry process such as vacuum deposition, ionization deposition, sputtering, or plasma deposition. Alternatively, instead of a dry process, a wet process can be used in which the layer is formed by dissolving the compound in a suitable solvent and applying a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0087] When layers are formed using methods such as vacuum deposition or solution coating, crystallization is less likely to occur, resulting in excellent stability over time. Furthermore, when forming films using coating methods, it is possible to combine the film with an appropriate binder resin.

[0088] Examples of the binder resins mentioned above include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0089] Furthermore, these binder resins may be used individually as homopolymers or copolymers, or as a mixture of two or more types. Additionally, known additives such as plasticizers, antioxidants, and UV absorbers may be used in combination as needed.

[0090] [Formation of the luminescent layer] In the organic light-emitting element of the present invention, the light-emitting layer is formed by a coating method because the compound represented by general formula (1) has high solubility in organic solvents. Examples of coating methods include spin coating, slit coating, printing, inkjet, dispensing, and spraying.

[0091] [Pixel circuit] The light-emitting device may have a pixel circuit connected to a light-emitting element. The pixel circuit may be an active-matrix type that independently controls the light emission of a first light-emitting element and a second light-emitting element. 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 light emission brightness of the light-emitting element, a transistor that controls the light emission timing, a capacitor that holds the gate voltage of the transistor that controls the light emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0092] 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 the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit.

[0093] The slope of the current-voltage characteristics of the transistors constituting the pixel circuit can be smaller than the slope of the current-voltage characteristics of the transistors constituting the display control circuit. The slope of the current-voltage characteristics can be measured using the so-called Vg-Ig characteristic.

[0094] The transistors that make up the pixel circuit are transistors connected to light-emitting elements, such as the first light-emitting element.

[0095] [Pixels] The organic light-emitting device has multiple pixels. Each pixel has subpixels that emit light of a different color from the others. The subpixels may each have, for example, RGB light-emitting colors.

[0096] A pixel emits light in a region also called the pixel aperture. This region is the same as the first region. 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.

[0097] The distance between subpixels may be 10 μm or less, specifically 8 μm, 7.4 μm, or 6.4 μm.

[0098] Pixels can take on known arrangements in a plan view. For example, they may be in a stripe arrangement, delta arrangement, pentile arrangement, or Bayer arrangement. The shape of subpixels in a plan view may be any known shape. For example, rectangles, rhombuses, hexagons, etc. Of course, even if it is not a precise shape, if it is close to a rectangle, it is included in the category of rectangles. The shape of subpixels and the pixel arrangement can be used in combination.

[0099] [Applications of the organic light-emitting element according to one embodiment of the present invention] An organic light-emitting element according to one embodiment of the present invention can be used as a component of a display device or lighting device. Other applications include exposure light sources for electrophotographic image forming apparatuses, backlights for liquid crystal display devices, and light-emitting devices with a color filter in a white light source.

[0100] The display device may also be an image information processing device that has an image input unit for receiving image information from an area CCD, linear CCD, memory card, etc., an information processing unit for processing the input information, and displays the input image on the display unit.

[0101] Furthermore, the display unit of the imaging device or inkjet printer may have a touch panel function. The driving method for this touch panel function may be infrared, capacitive, resistive, or electromagnetic induction, and is not particularly limited. The display device may also be used as the display unit of a multifunction printer.

[0102] Next, the display device according to this embodiment will be described with reference to the drawings.

[0103] Figure 1 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to this organic light-emitting element. The transistor is an example of an active element. The transistor may also be a thin-film transistor (TFT).

[0104] Figure 1(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The light emission color may be distinguished by the wavelength emitted from the light-emitting layer, or the light emitted from the sub-pixel may be selectively transmitted or color-converted by a color filter or the like. Each sub-pixel has a reflective electrode 2 which is a first electrode, an insulating layer 3 covering the end of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, a transparent electrode 5, a protective layer 6, and a color filter 7 on an interlayer insulating layer 1.

[0105] The interlayer insulating layer 1 may have transistors and capacitive elements placed in the layer below or inside it. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0106] The insulating layer 3 is also called the bank or pixel isolation layer. It covers the edge of the first electrode and surrounds the first electrode. The portion without the insulating layer is in contact with the organic compound layer 4 and becomes the light-emitting region.

[0107] The organic compound layer 4 includes a hole injection layer 41, a hole transport layer 42, a first light-emitting layer 43, a second light-emitting layer 44, and an electron transport layer 45.

[0108] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0109] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is shown as a single layer, it may consist of multiple layers. Each layer may contain an inorganic compound layer and an organic compound layer.

[0110] The color filters 7 are classified into 7R, 7G, and 7B according to their color. The color filters may be formed on a planarization film (not shown). The color filters may also have a resin protective layer (not shown). Alternatively, the color filters may be formed on a protective layer 6, or they may be bonded together after being placed on an opposing substrate such as a glass substrate.

[0111] The display device 100 in Figure 1(b) shows an organic light-emitting element 26 and a TFT 18 as 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 18 such as a TFT is placed on the insulating layer, and the gate electrode 13, gate insulating film 14, and semiconductor layer 15 of the active element are arranged therein. The TFT 18 is also composed of a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. The anode 21 and the source electrode 17 that constitute the organic light-emitting element 26 are connected via a contact hole 20 provided in the insulating film.

[0112] Note that the method of electrical connection between the electrodes (anode, cathode) included in the organic light-emitting element 26 and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the configuration shown in Figure 1(b). In other words, it is sufficient if either the anode or cathode is electrically connected to either the source electrode or the drain electrode of the TFT. TFT refers to a thin-film transistor.

[0113] In the display device 100 shown in Figure 1(b), the organic compound layer is depicted as a single layer, but the organic compound layer 22 may consist of multiple layers. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce the degradation of the organic light-emitting element.

[0114] In the display device 100 shown in Figure 1(b), a transistor is used as the switching element, but other switching elements may be used instead.

[0115] Furthermore, the transistor used in the display device 100 in Figure 1(b) is not limited to a transistor using a single-crystal silicon wafer, but may also be a thin-film transistor having an active layer on an insulating surface of the substrate. Examples of active layers include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0116] The transistors included in the display device 100 in Figure 1(b) may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the transistors are manufactured by processing the substrate itself, such as a Si substrate. In other words, having transistors within a substrate can be seen as the substrate and transistors being formed as a single unit.

[0117] The organic light-emitting element according to this embodiment has its luminescence controlled by a TFT, which is an example of a switching element, and by providing multiple organic light-emitting elements on the surface, an image can be displayed using the luminescence of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor made of low-temperature polysilicon, or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "within the substrate." Whether to provide a transistor within the substrate or to use a TFT is selected depending on the size of the display area; for example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0118] Figure 2 is a schematic diagram showing 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. Flexible printed circuits FPCs 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, or it may be provided in a different location even if it is a portable device.

[0119] The display device according to this embodiment may have a color filter having red, green, and blue colors. The color filter may have the red, green, and blue colors arranged in a delta array.

[0120] The display device according to this embodiment may be used in the display unit of a mobile terminal. In that case, it may have both display and operation functions. Examples of mobile terminals include smartphones and other mobile phones, tablets, and head-mounted displays.

[0121] The display device according to this embodiment may be used in the display unit of an imaging device having an optical unit with multiple lenses and an image sensor that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the image sensor. Furthermore, the display unit may be a display unit exposed to the outside of the imaging device or a display unit located inside the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0122] Figure 3(a) 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 have a display device according to this embodiment. In that case, the display device may display not only the image to be captured, but also environmental information, imaging instructions, etc. Environmental information may include the intensity of ambient light, the direction of ambient light, the speed at which the subject is moving, the possibility of the subject being obscured by an obstacle, etc.

[0123] Since the optimal timing for imaging is very short, it is best to display the information as quickly as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of the present invention, because organic light-emitting elements have a fast response speed. Display devices using organic light-emitting elements can be used more suitably than liquid crystal display devices, which require a fast display speed.

[0124] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses that form an image on the image sensor housed in the housing 1104. The focus can be adjusted by adjusting the relative positions of the multiple lenses. This operation can also be performed automatically. The imaging device may also be called a photoelectric converter. The photoelectric converter may not capture images sequentially, but may include imaging methods such as detecting the difference from the previous image or extracting from an image that is always being recorded.

[0125] Figure 3(b) is a schematic diagram showing 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 response unit. The operation unit may also be a biometric recognition unit that recognizes fingerprints to unlock or otherwise perform actions. An electronic device having a communication unit can also be called a communication device. The electronic device may further have a camera function by including a lens and an image sensor. Images captured by the camera function are displayed on the display unit. Examples of electronic devices include smartphones and laptop computers.

[0126] Figure 4 is a schematic diagram showing an example of a display device according to this embodiment. Figure 4(a) is 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 the light-emitting device according to this embodiment.

[0127] It has a frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in Figure 4(a). The bottom edge of the frame 1301 may also serve as the base.

[0128] Furthermore, the frame 1301 and the display section 1302 may be curved. Their radius of curvature may be between 5000 mm and 6000 mm.

[0129] Figure 4(b) is a schematic diagram showing another example of the display device according to this embodiment. The display device 1310 in Figure 4(b) is configured to be foldable and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have light-emitting devices according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single display device without seams. The first display unit 1311 and the second display unit 1312 can be separated at a 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 together display a single image.

[0130] Figure 5(a) is a schematic diagram showing 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 film 1404, and a light diffusion section 1405. The light source may have an organic light-emitting element according to this embodiment. The optical filter may be a filter that improves the color rendering of the light source. The light diffusion section can effectively diffuse the light from the light source, such as for lighting up, and deliver light over a wide area. The optical filter and light diffusion section may be provided on the light-emitting side of the lighting. A cover may be provided on the outermost part as needed.

[0131] The lighting device is, for example, a device for illuminating a room. The lighting device may emit white light, cool white light, or any other color from blue to red. It may have a dimming circuit to adjust the brightness of these lights. The lighting device may have the organic light-emitting element of the present invention and a power supply circuit connected thereto. The power supply circuit is a circuit that converts AC voltage to DC voltage. White light has a color temperature of 4200K, and cool white light has a color temperature of 5000K. The lighting device may have a color filter.

[0132] Furthermore, the lighting device according to this embodiment may have a heat dissipation section. The heat dissipation section releases heat from inside the device to the outside, and examples include metals with high specific heat, liquid silicon, etc.

[0133] Figure 5(b) is a schematic diagram of an automobile, which is an example of a mobile body according to this embodiment. The automobile has a taillight, which is an example of a lighting device. The automobile 1500 has a taillight 1501, and may be configured to illuminate when the brakes are applied or the like.

[0134] The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp may have a protective member to protect the organic EL element. The protective member has a reasonably high strength and can be made of any transparent material, but it is preferably made of polycarbonate or the like. A frangic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.

[0135] The automobile 1500 may have a body 1503 and windows 1502 attached thereto. The windows may be transparent displays, unless they are windows for checking the front and rear of the automobile. The transparent displays may have organic light-emitting elements according to this embodiment. In this case, the constituent materials such as electrodes of the organic light-emitting element are made of transparent members.

[0136] The mobile body according to this embodiment may be a ship, aircraft, drone, etc. The mobile 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 an organic light-emitting element according to this embodiment.

[0137] Referencing Figure 6, examples of applications of the display devices of each embodiment described above will be explained. The display device can be applied to systems that can be worn as wearable devices such as smart glasses, HMDs, and smart contact lenses. The imaging display device used in such applications comprises an imaging device capable of photoelectric conversion of visible light and a display device capable of emitting visible light.

[0138] Figure 6(a) illustrates a pair of glasses 1600 (smart glasses) according to one application example. An imaging device 1602, such as a CMOS sensor or SPAD, is provided on the front surface of the lens 1601 of the glasses 1600. In addition, the display devices of each embodiment described above are provided on the back surface of the lens 1601.

[0139] The eyeglasses 1600 further include a control device 1603. The control device 1603 functions as a power supply that provides power to the imaging device 1602 and the display device according to each embodiment. The control device 1603 also controls the operation of the imaging device 1602 and the display device. The lens 1601 has an optical system formed therein for focusing light onto the imaging device 1602.

[0140] Figure 6(b) illustrates a pair of glasses 1610 (smart glasses) according to one application example. The glasses 1610 have a control device 1612, which is equipped with an imaging device equivalent to an imaging device 1602 and a display device. The lens 1611 has an optical system formed therein for projecting light emitted from the imaging device and the display device within the control device 1612, and an image is projected onto the lens 1611. The control device 1612 functions as a power supply to provide power to the imaging device and the display device, and also controls the operation of the imaging device and the display device. The control device may have a gaze detection unit that detects the wearer's gaze. Gaze detection may use infrared light. The infrared light emitter emits infrared light towards the eyeball of the user who is fixating on the displayed image. The imaging unit, which has a photodetector, detects the reflected light from the eyeball of the emitted infrared light, thereby obtaining an image of the eyeball. By having a reduction means that reduces the light from the infrared light emitter to the display unit in planar view, the degradation of image quality is reduced.

[0141] The user's gaze towards the displayed image is detected from an image of the eyeball obtained by imaging with infrared light. Any known method can be applied to gaze detection using an image of the eyeball. For example, a gaze detection method based on the Purkinje image obtained by the reflection of the irradiated light from the cornea can be used.

[0142] More specifically, gaze detection processing is performed based on the pupil-corneal reflection method. Using the pupil-corneal reflection method, a gaze vector representing the orientation (rotation angle) of the eyeball is calculated based on the pupil image and Purkinje image contained in the captured image of the eyeball, thereby detecting the user's gaze.

[0143] A display device according to one embodiment of the present invention includes an imaging device having a light-receiving element, and may control the display image of the display device based on the user's gaze information from the imaging device.

[0144] Specifically, the display device determines a first field of view that the user is fixated on, and a second field of view other than the first field of view, based on gaze information. The first and second field of view may be determined by the control device of the display device, or they may be determined by an external control device and received by the display device. Within the display area of ​​the display device, the display resolution of the first field of view may be controlled to be higher than the display resolution of the second field of view. In other words, the resolution of the second field of view may be lower than that of the first field of view.

[0145] Furthermore, the display area has a first display area and a second display area different from the first display area, and based on gaze information, the area with higher priority is determined from the first display area and the second display area. The first and second view areas may be determined by the control device of the display device, or they may be determined by an external control device and received. The resolution of the high-priority area may be controlled to be higher than the resolution of the areas other than the high-priority area. In other words, the resolution of areas with relatively lower priority may be lowered.

[0146] AI may be used to determine the primary field of view and high-priority areas. The AI ​​may be a model configured to estimate the angle of gaze and the distance to the target object at the end of the line of sight from the image of the eye, using the image of the eye and the direction the eye was actually looking in that image as training data. The AI ​​program may be installed in the display device, the imaging device, or an external device. If installed in an external device, it will be transmitted to the display device via communication.

[0147] When display control is based on visual detection, this method is preferably applicable to smart glasses that further include an imaging device for capturing images of the surrounding environment. The smart glasses can display the captured external information in real time.

[0148] As described above, by using the device employing the organic light-emitting element according to this embodiment, stable display with good image quality is possible even during long-term display.

[0149] Figure 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 photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fuser 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoreceptor 27. This exposure light source 28 has an organic light-emitting element according to this embodiment. The developing unit 31 has toner or the like. The charging unit 30 charges the photoreceptor 27. The transfer unit 32 transfers the developed image to a storage medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fuser 35 fixes the image formed on the recording medium 34.

[0150] Figures 7(b) and 7(c) are diagrams showing the exposure light source 28, schematic diagrams showing how multiple light-emitting units 36 are arranged on a long substrate. Arrows 37 indicate the direction of the column in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis of rotation of the photoreceptor 27. This direction can also be called the long axis direction of the photoreceptor 27. Figure 7(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoreceptor 27. Figure 7(c) is a different configuration from Figure 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 located at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged with intervals between them. 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. That is, multiple light-emitting units 36 are also arranged with intervals between them in the row direction. The arrangement in Figure 7(c) can also be described as a grid pattern, a houndstooth pattern, or a checkerboard pattern. [Examples]

[0151] The present invention will be described below with reference to examples. However, the present invention is not limited to these examples.

[0152] [Example 1 (Synthesis of Compound (1)] Compound (1) was synthesized using the following procedure. [ka]

[0153] 2-(2-(tert-butyl)-7,7-dimethyl-7H-indeno[1,2-a]pyren-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (270 mg), 4,6-dichloropyrimidine (40 mg), tetrakistriphenylphosphine palladium (5 mg), potassium carbonate (177 mg), dioxane (10 mL), and water (5 mL) were added to a 50 ml round-bottom flask and stirred at 90°C for 10 hours. After extraction with dichloromethane, the mixture was purified by silica gel column chromatography. Toluene (60 ml) was added for dispersion washing, the precipitated solid was filtered and dried to obtain 138 mg of compound (1) as a yellow solid.

[0154] [Example 2 (Synthesis of Compound (5)] Compound (5) was synthesized using the following procedure. [ka]

[0155] 2-(2-(tert-butyl)-7,7-dimethyl-7H-indeno[1,2-a]pyren-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (325 mg), 2,4-dichloro-1,3,5-triazine (46 mg), tetrakistriphenylphosphine palladium (6 mg), potassium carbonate (214 mg), dioxane (15 mL), and water (7.5 mL) were added to a 50 ml round-bottom flask and stirred at 90°C for 14 hours. After extraction with dichloromethane, the mixture was purified by silica gel column chromatography. Toluene (20 ml) was added and recrystallized, and the precipitated solid was filtered and dried to obtain 100 mg of compound (5) as a yellow-green solid.

[0156] [Examples 4 to 6, Comparative Example 1 (Evaluation of Thermal Properties)] The weight loss onset temperatures under atmospheric pressure for compounds (1), (5), (10), and compound A (as a comparative example) were measured using a thermogravimetric differential thermal analyzer STA7200 (manufactured by Hitachi High-Tech Science Corporation). Additionally, the sublimation temperature was defined as the temperature at which the weight decay rate reached 5% under vacuum (2 Pa) and measured using a thermogravimetric differential thermal analyzer TA7000 (manufactured by Hitachi High-Tech Science Corporation). The results are shown in Table 1. [Table 1]

[0157] Table 1 shows that the organic compound represented by general formula (1) exhibited lower weight loss onset temperatures and sublimation temperatures compared to Comparative Example 1. This is considered to be due to the use of a heteroaryl group having a nitrogen atom in Ar. Therefore, it was found that organic compounds in general formula (1) in which Ar is a substituted or unsubstituted heteroaryl group are organic compounds with excellent sublimation properties.

[0158] [Example 7, Comparative Example 2 (Evaluation of Organic EL Devices)] In Example 7, compound (1) was used as a guest in the light-emitting layer, and an organic light-emitting device was fabricated using the method described below, with the configuration of an anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode sequentially provided on a substrate.

[0159] A transparent conductive support substrate (ITO substrate) was used, on which ITO was deposited as the anode to a thickness of 100 nm by sputtering on a glass substrate. On this ITO substrate, the following organic compound layer and electrode layer were added. -5 The film was continuously deposited by vacuum deposition using resistance heating in a Pa vacuum chamber. The electrode area at this time was 3 mm². 2 It was made to achieve this. [Table 2]

[0160] Next, to prevent degradation of the organic light-emitting element due to moisture adsorption, a protective glass plate was placed over it in a dry air atmosphere and sealed with an acrylic resin adhesive. The organic light-emitting element was obtained in this manner. For the obtained organic light-emitting element, an IVL (current-voltage-luminance) measurement was performed with the ITO electrode as the anode and the Al electrode as the cathode. The normalized EL spectrum is shown in Figure 8(a).

[0161] Furthermore, an organic light-emitting element was fabricated in the same manner as in Example 7, except that the guest material was changed to compound A, and this was designated as Comparative Example 2. The obtained element was also subjected to IVL measurement in the same manner as in Example 7.

[0162] 10 mA / cm² for organic light-emitting elements in Example 7 and Comparative Example 2 2 External quantum efficiency (EQE) at time, and 5 mA / cm² for organic light-emitting diodes. 2 When the initial brightness is set to 100%, the current is 5mA / cm². 2 Table 3 shows the relative values ​​of the durability time (LT80) until the brightness reaches 80% when continuously operated (compound A is set to 1). [Table 3]

[0163] Table 3 shows that in general formula (1), organic compounds in which Ar is a substituted or unsubstituted heteroaryl group exhibited superior external quantum efficiency and device lifetime compared to comparative example compound A.

[0164] [Example 8] Synthesis of compound (25) Compound (25) was synthesized using the following procedure. [ka]

[0165] 2-(2-(tert-butyl)-7,7-dimethyl-7H-indeno[1,2-a]pyren-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (280 mg), 2,7-dibromo-9,9'-spirobi[fluorene] (126 mg), tetrakistriphenylphosphine palladium (9 mg), potassium carbonate (147 mg), dioxane (10 mL), and water (5 mL) were added to a 50 mL round-bottom flask and stirred at 90°C for 10 hours. After extraction with dichloromethane, the mixture was purified by gel permeation chromatography. 60 mg of compound (1) was obtained as a yellow solid.

[0166] [Example 9] Synthesis of compound (29) Compound (29) was synthesized using the following procedure. [ka]

[0167] 2-(2-(tert-butyl)-7,7-dimethyl-7H-indeno[1,2-a]pyren-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (280 mg), 2,2'-dibromo-9,9'-spirobi[fluorene] (126 mg), tetrakistriphenylphosphine palladium (9 mg), potassium carbonate (147 mg), dioxane (10 mL), and water (5 mL) were added to a 50 ml round-bottom flask and stirred at 90°C for 10 hours. After extraction with dichloromethane, the mixture was purified by gel permeation chromatography. 50 mg of compound (5) was obtained as a yellow solid.

[0168] [Examples 10 and 11, Comparative Example 3] (Evaluation of solubility) 50 mg each of compounds (25) and (29) obtained in the examples, and compound A as a comparative example, were placed in a sample bottle with 1 ml of toluene and stirred at room temperature to check for dissolution. The results are shown in Table 4. In Table 4, ○ indicates that the compound dissolved in the solvent, and △ indicates that the compound was poorly soluble in the solvent and that the compound remained in the solution as visually confirmed. [Table 4]

[0169] Table 4 shows that compounds (25) and (29), which are embodiments of one invention, exhibited improved solubility compared to Comparative Example 3. Therefore, it was found that organic compounds in which Ar has a spirofluorene skeleton are organic compounds with excellent solubility.

[0170] [Example 12 (PL spectrum in solution)] Compounds (25), (29), and compound A as a comparative example were each added to toluene in a 10-minute solution. -5 The wavelength of the peak top in the PL spectrum of the adjusted solution to which mol / L was added was measured.

[0171] [Examples 13 and 14, Comparative Example 4 (Evaluation of Organic EL Devices)] In Example 13, compound (25) was used as the guest compound for the light-emitting layer, and an organic light-emitting device was fabricated using the method described below, with the configuration of an anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode sequentially provided on a substrate.

[0172] A transparent conductive support substrate (ITO substrate) was used, which consisted of a glass substrate on which an ITO film was deposited as the anode to a thickness of 100 nm using the sputtering method. Next, this glass substrate with the ITO film was ultrasonically cleaned sequentially with acetone and isopropyl alcohol (IPA), followed by boiling with IPA and drying. Then, it was UV / ozone cleaned. The glass substrate processed in this manner was used as a transparent conductive support substrate.

[0173] Next, as the hole transport layer, PEDOT:PSS (product name: CLEVIOS) TM P VP AI 4083) was deposited by spin coating. The thickness of the hole injection transport layer is 70 nm.

[0174] Next, a toluene solution of compound (25):EM33 (concentration: 1.0 wt%, compound (25):EM33 = 1:99) was prepared as the light-emitting layer, and this solution was then deposited onto the hole injection transport layer by spin coating. The thickness of the light-emitting layer was 20 nm.

[0175] On this light-emitting layer, a hole blocking (HB) layer, an electron transport layer, and a metal electrode layer are placed. -5 The film was continuously deposited by vacuum deposition using resistance heating in a Pa vacuum chamber. The electrode area at this time was 3 mm². 2 It was manufactured to achieve the following. The layer structure is shown below. [Table 5]

[0176] Next, to prevent degradation of the organic light-emitting element due to moisture adsorption, a protective glass plate was placed over it in a dry air atmosphere and sealed with an acrylic resin adhesive. The organic light-emitting element was obtained in this manner. The obtained organic light-emitting element was subjected to EL spectrum measurement with the ITO electrode as the anode and the Al electrode as the cathode.

[0177] An organic light-emitting element was fabricated in the same manner as in Example 13, except that the guest compound was changed to compound (29), and this was designated as Example 14. The resulting element was then subjected to EL spectrum measurement in the same manner as in Example 13.

[0178] An organic light-emitting element was fabricated in the same manner as in Example 13, except that the guest compound was changed to compound A, and this was designated as Comparative Example 4. The resulting element was then subjected to EL spectrum measurement in the same manner as in Example 13.

[0179] The normalized EL spectra obtained in Examples 13 and 14 and Comparative Example 4 are shown in Figure 8(b).

[0180] The wavelength change of the first peak top was calculated between the obtained EL spectrum and the PL spectrum in the solution measured in Example 12. The full width at half maximum (FWHM) of the EL spectrum was also measured. The results are shown in Table 6. [Table 6]

[0181] Table 6 shows that compounds (25) and (29), which are embodiments of the present invention, exhibit less change in the emission wavelength of the first peak top in solution and in the device compared with comparative example compound A, and also have a smaller full width at half maximum.

[0182] In general formula (1), when Ar is a skeleton having spirofluorene, the organic compound according to the present invention has a bulky skeleton, and therefore it is thought that intermolecular stacking can be suppressed. As a result, it is thought that the full width at half maximum of the absorption wavelength can be narrowed.

[0183] Based on the above, the present invention can provide organic compounds and organic light-emitting devices with excellent luminescence properties. Specifically, it can provide organic compounds with excellent sublimation properties or solubility. Therefore, it can provide organic light-emitting devices with excellent luminescence efficiency or device lifetime. Furthermore, it can provide organic light-emitting devices with minimal color change between the solution state and the organic light-emitting device, and with excellent color purity.

[0184] Furthermore, the present invention can also take the following configuration.

[0185] (Composition 1) An organic compound characterized by being represented by general formula (1). Ip-L 1 -Ar-L 2 -FL (1) In general formula (1), Ip represents a skeleton having an indenopylene, Ar represents a skeleton having a substituted or unsubstituted heteroaryl group or a spirofluorene, and FL represents an indenopylene skeleton or a skeleton having the structure represented by general formula (2). 1 and L 2 The group is independently selected from directly bonded, substituted, or unsubstituted arylene groups. [ka] In general formula (2), X is an oxygen atom, a sulfur atom, a nitrogen atom, and CR. 1 R 2 , or NR 3 Represents R 1 ~R 3 Each of these is independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0186] (Configuration 2) The organic compound according to configuration 1, characterized in that Ip has a 7H-indeno[1,2-a]pyrene skeleton in general formula (1).

[0187] (Composition 3) The organic compound according to configuration 1 or 2, characterized in that in general formula (1), FL has an indenopylene skeleton or a fluorene skeleton.

[0188] (Composition 4) An organic compound according to any one of the constructs 1 to 3, characterized in that, in general formula (1), Ar is a heteroaryl group having a nitrogen atom.

[0189] (Composition 5) The organic compound according to configuration 4, characterized in that in general formula (1), Ar has at least one skeleton from among the pyridine skeleton, pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton, triazine skeleton, quinoline skeleton, isoquinoline skeleton, and naphthyridine skeleton.

[0190] (Composition 6) The organic compound according to configuration 5, characterized in that in general formula (1), Ar has at least one skeleton from among a pyridine skeleton, a pyrimidine skeleton, and a triazine skeleton.

[0191] (Composition 7) An organic compound according to any one of the constructs 1 to 6, characterized in that in general formula (1), Ar is a 9,9'-spirobifluorene skeleton.

[0192] (Composition 8) An organic compound according to any one of the claims 1 to 7, characterized in that Ip has an alkyl group having 1 to 4 carbon atoms in general formula (1).

[0193] (Composition 9) The organic compound according to configuration 8, characterized in that Ip in general formula (1) is a methyl group or a tert-butyl group.

[0194] (Composition 10) The organic compound according to any one of the claims 1 to 9, characterized in that in general formula (1), FL has an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms.

[0195] (Composition 11) The organic compound according to configuration 10, characterized in that in general formula (1), FL has a methyl group or a tert-butyl group.

[0196] (Composition 12) An organic compound according to any one of the constructs 1 to 11, characterized in that Ar has an alkyl group having 1 to 4 carbon atoms in general formula (1).

[0197] (Composition 13) The organic compound according to configuration 12, characterized in that Ar has a tert-butyl group in general formula (1).

[0198] (Composition 14) The first electrode and the second electrode, An organic light-emitting element having an organic compound layer disposed between the aforementioned first electrode and the aforementioned second electrode, The organic light-emitting element is characterized in that the organic compound layer contains the organic compound described in any one of the components 1 to 13.

[0199] (Composition 15) The aforementioned organic compound layer has a light-emitting layer, The organic light-emitting element according to configuration 14, characterized in that the light-emitting layer contains the organic compound.

[0200] (Composition 16) The light-emitting layer further comprises the first compound, The organic light-emitting element according to configuration 15, characterized in that the first compound is a compound with a lower minimum excitation singlet energy than the organic compound.

[0201] (Composition 17) The organic light-emitting element according to configuration 15 or 16, characterized in that the first compound is composed of a hydrocarbon.

[0202] (Composition 18) The light-emitting layer further comprises a second compound, The organic compound according to configuration 16 or 17, characterized in that the second compound is a compound with a lower excitation singlet energy than the organic compound.

[0203] (Composition 19) A display device having a plurality of pixels, wherein at least one of the plurality of pixels comprises an organic light-emitting element according to any one of the configurations 14 to 18 and a transistor connected to the organic light-emitting element.

[0204] (Composition 20) It comprises an optical unit having multiple lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays the image captured by the image sensor. The photoelectric conversion device is characterized in that the display unit has the organic light-emitting element according to any one of Configurations 14 to 18.

[0205] (Configuration 21) An electronic device comprising: a display unit having the organic light-emitting element according to any one of Configurations 14 to 18; a housing provided with the display unit; and a communication unit provided in the housing and communicating with the outside.

[0206] (Configuration 22) An illumination device comprising: a light source having the organic light-emitting element according to any one of Configurations 14 to 18; and a light diffusing unit or an optical film that transmits light emitted from the light source.

[0207] (Configuration 23) A moving body comprising: a lamp having the organic light-emitting element according to any one of Configurations 14 to 18; and a body provided with the lamp. [[ID=​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​19 Insulating film 20 Contact hole 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting device 100 Display device 1000 Display device 1001 Upper cover 1002 Flexible printed circuit 1003 Touch panel 1004 Flexible printed circuit 1005 Display panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation unit 1104 Housing 1200 Electronic device 1201 Display unit 1202 Operation unit 1203 Housing 1300 Display device 1301 Frame 1302 Display unit 1303 Base 1310 Display device 1311 First display unit 1312 Second display unit 1313 Housing 1314 Bend point 1400 Lighting device * 1401 Housing 1402 Light source 1403 Circuit board 1404 Optical film 1405 Light diffusing part 1500 Automobile 1501 Tail lamp 1502 Window 1503 Body 1600 Smart Glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart Glasses 1611 Lens 1612 Control device

Claims

1. An organic compound characterized by being represented by general formula (1). I0-L １ -A-L ２ -FL (1) In general formula (1), Ip represents a skeleton containing indenopylene, Ar represents a skeleton containing spirofluorene, and FL represents an indenopylene skeleton or a skeleton having a structure represented by general formula (2). １ and L ２ The group is independently selected from directly bonded, substituted, or unsubstituted arylene groups. 【Chemistry 1】 In general formula (2), X represents an oxygen atom, a sulfur atom, a nitrogen atom, CR １ R ２ , or NR ３ , and R １ to R ３ are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

2. An organic compound characterized by being represented by general formula (1). Ip-L 1 -Ar-L 2 -FL (1) In general formula (1), Ip represents a skeleton having an indenopylene, Ar represents a heteroaryl group having a substituted or unsubstituted nitrogen atom, and FL represents an indenopylene skeleton or a skeleton having the structure represented by general formula (2). L1 and L2 are independently selected from directly bonded or substituted or unsubstituted arylene groups. In general formula (2), X represents CR1 R2, where R1 to R3 are independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

3. The organic compound according to claim 1 or 2, characterized in that Ip in general formula (1) has a 7H-indeno[1,2-a]pyrene skeleton.

4. The organic compound according to claim 1, characterized in that in general formula (1), FL has an indenopylene skeleton or a fluorene skeleton.

5. The organic compound according to claim 2, characterized in that, in general formula (1), the heteroaryl group having a nitrogen atom is a heteroaryl group having 3 to 12 carbon atoms.

6. The organic compound according to claim 5, characterized in that in general formula (1), Ar has at least one skeleton from among the pyridine skeleton, pyrimidine skeleton, pyrazine skeleton, pyridazine skeleton, triazine skeleton, quinoline skeleton, isoquinoline skeleton, and naphthyridine skeleton.

7. The organic compound according to claim 6, characterized in that in general formula (1), Ar has at least one skeleton selected from a pyridine skeleton, a pyrimidine skeleton, and a triazine skeleton.

8. The organic compound according to claim 1, characterized in that Ar is a 9,9'-spirobifluorene skeleton in general formula (1).

9. The organic compound according to claim 1 or 2, characterized in that Ip has an alkyl group having 1 to 4 carbon atoms in general formula (1).

10. The organic compound according to claim 9, characterized in that Ip in general formula (1) is a methyl group or a tert-butyl group.

11. The organic compound according to claim 1 or 2, characterized in that in general formula (1), FL has an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms.

12. The organic compound according to claim 11, characterized in that in general formula (1), FL has a methyl group or a tert-butyl group.

13. The organic compound according to claim 1 or 2, characterized in that Ar has an alkyl group having 1 to 4 carbon atoms in general formula (1).

14. The organic compound according to claim 13, characterized in that Ar has a tert-butyl group in general formula (1).

15. The first electrode and the second electrode, An organic light-emitting element having an organic compound layer disposed between the first electrode and the second electrode, The organic light-emitting element is characterized in that the organic compound layer contains the organic compound described in claim 1 or 2.

16. The aforementioned organic compound layer has a light-emitting layer, The organic light-emitting element according to claim 15, characterized in that the light-emitting layer contains the organic compound.

17. The light-emitting layer further comprises the first compound, The organic light-emitting element according to claim 16, characterized in that the first compound is a compound with a lower minimum excitation singlet energy than the organic compound.

18. The organic light-emitting element according to claim 17, characterized in that the first compound is composed of a hydrocarbon.

19. The light-emitting layer further comprises a second compound, The organic light-emitting element according to claim 17, characterized in that the second compound is a compound with a lower excitation singlet energy than the organic compound.

20. A display device having a plurality of pixels, wherein at least one of the plurality of pixels is an organic light-emitting element according to any one of claims 15 to 19 and a transistor connected to the organic light-emitting element.

21. It comprises an optical unit having multiple lenses, an image sensor that receives light that has passed through the optical unit, and a display unit that displays the image captured by the image sensor. The photoelectric conversion device is characterized in that the display unit has an organic light-emitting element as described in any one of claims 15 to 19.

22. An electronic device comprising: a display unit having an organic light-emitting element as described in any one of claims 15 to 19; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

23. A lighting device comprising a light source having an organic light-emitting element as described in any one of claims 15 to 19, and a light-diffusing portion or optical film that transmits light emitted by the light source.

24. A mobile body which is an automobile, ship, aircraft, or drone, The mobile body is characterized by comprising a lamp having an organic light-emitting element as described in any one of claims 15 to 19, and a body on which the lamp is provided.

25. It comprises a photoreceptor and an exposure light source for exposing the photoreceptor, The image forming apparatus is characterized in that the exposure light source has an organic light-emitting element as described in any one of claims 15 to 19.

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