Organic compound and organic light-emitting device

Abstract

To provide an organic compound that enables formation of a film with superior thermal stability, and an organic light-emitting device that contains the organic compound and demonstrates a superior service life.SOLUTION: The present invention provides an organic compound that has an oligophenylene structure with 4 to 7 phenylene groups in a molecule, with the phenyl groups at both terminals being substituted with an aryl group or a heterocyclic group constituted by three or more fused rings.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 pair of electrodes 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 light-emitting element emits light.

[0003] Recent advances in organic light-emitting devices are remarkable, enabling low drive voltage, diverse emission wavelengths, fast response times, and miniaturization and weight reduction of light-emitting devices.

[0004] Incidentally, there has been a great deal of effort to create compounds suitable for organic light-emitting devices. This is because creating compounds with excellent device lifespan is crucial for providing high-performance organic light-emitting devices.

[0005] As an example of compounds created to date, compound 1-A is described in Patent Document 1, compound 1-B is described in Patent Document 2, compound 1-C is described in Patent Document 3, and compound 1-D is described in Patent Document 4. [ka] [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] International Publication No. 2009 / 021126 [Patent Document 2] International Publication No. 2012 / 133644 [Patent Document 3] International Publication No. 2012 / 153780 [Patent Document 4] International Publication No. 2012 / 050008 [Overview of the project] [Problems that the invention aims to solve]

[0007] Because the molecules of all the above compounds tend to aggregate in the film, using these compounds in organic light-emitting devices presents challenges in terms of device lifespan.

[0008] This invention has been made in view of the above problems, and its purpose is to provide an organic compound in which molecules are less likely to aggregate in a membrane. [Means for solving the problem]

[0009] The organic compound according to the present invention is characterized by being represented by the general formula [1]. [ka] In general formula [1], Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl groups consisting of three or more rings, or substituted or unsubstituted heterocyclic groups consisting of three or more rings. Ar1 and Ar2 are represented by different skeletons. When Ar1 and Ar2 are dibenzothiophene skeletons or dibenzofuran skeletons, the organic compound has at least one substituent.

[0010] The substituent represented by R is selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, or a cyano group. If there are multiple Rs, they may be the same or different.

[0011] n is an integer from 2 to 5, and m1 to m3 are each an integer from 0 to 4.

Advantages of the Invention

[0012] According to the present invention, when the organic compound according to the present invention is used in an organic light-emitting device, an organic light-emitting device excellent in element lifetime can be provided.

Brief Description of the Drawings

[0013] [Figure 1] (a) It is a schematic cross-sectional view showing an example of a pixel of a display device according to an embodiment of the present invention. (b) It is a schematic cross-sectional view of an example of a display device using an organic light-emitting device according to an embodiment of the present invention. [Figure 2] It is a schematic diagram showing an example of a display device according to an embodiment of the present invention. [Figure 3] (a) It is a schematic diagram showing an example of an imaging device according to an embodiment of the present invention. (b) It is a schematic diagram showing an example of an electronic device according to an embodiment of the present invention. [Figure 4] (a) It is a schematic diagram showing an example of a display device according to an embodiment of the present invention. (b) It is a schematic diagram showing an example of a foldable display device. [Figure 5] (a) It is a schematic diagram showing an example of a lighting device according to an embodiment of the present invention. (b) It is a schematic diagram showing an example of an automobile having a vehicle lamp according to an embodiment of the present invention. [Figure 6] (a) It is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. (b) It is a schematic diagram showing a form having an imaging device as an example of a wearable device according to an embodiment of the present invention. [Figure 7] (a) It is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the present invention. (b) It is a schematic diagram showing an example of an exposure light source of an image forming apparatus according to an embodiment of the present invention. (c) It is a schematic diagram showing an example of an exposure light source of an image forming apparatus according to an embodiment of the present invention. [Figure 8] It is an emission spectrum of exemplary compound A4 and comparative compound 1-B obtained by phosphorescence mode measurement. [Modes for carrying out the invention]

[0014] In this specification, examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, and iodine.

[0015] 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 1-adamantyl group, and a 2-adamantyl group.

[0016] The alkoxy group may be any alkoxy group having 1 to 10 carbon atoms. Examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, and a benzyloxy group.

[0017] Examples of amino groups include, but are not limited to, N-methylamino group, N-ethylamino group, N,N-dimethylamino group, N,N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N,N-dibenzyloamino group, anilino group, N,N-diphenylamino group, N,N-dinaphthylamino group, N,N-difluorenylamino group, N-phenyl-N-tolylamino group, N,N-ditolylamino group, N-methyl-N-phenylamino group, N,N-dianisorylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tert-butylphenyl)amino group, N-phenyl-N-(4-trifluoromethylphenyl)amino group, and N-piperidyl group.

[0018] Examples of aryloxy groups include, but are not limited to, phenoxy groups.

[0019] Examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0020] Examples of silyl groups include, but are not limited to, trimethylsilyl and triphenylsilyl groups.

[0021] 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, fluoranthenyl, and triphenylenyl groups.

[0022] The heterocyclic group may be any heterocyclic group having 3 to 20 carbon atoms. Examples include, but are not limited to, pyridyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, phenanthrolyl, dibenzofuranyl, and dibenzothiophenyl groups.

[0023] The substituents that the alkyl groups, alkoxy groups, amino groups, aryloxy groups, silyl groups, aryl groups, and heterocyclic groups may further have include, but are not limited to, halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl groups; alkoxy groups such as methoxy, ethoxy, and propoxy groups; amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino groups; aryloxy groups such as phenoxy groups; aryl groups such as phenyl and biphenyl groups; heterocyclic groups such as pyridyl and pyrrolyl groups; and cyano groups.

[0024] (1)Organic compounds First, let me explain the organic compounds according to the present invention.

[0025] In this specification, "different skeletons" means that even if the skeletons are the same, if the bond positions are different, they are considered to be different skeletons. Specifically, the 2-dibenzofuranyl group and the 3-dibenzofuranyl group have the same dibenzofuran skeleton, but because their bond positions are different, they are considered to be different skeletons.

[0026] The organic compound according to the present invention is a compound represented by the general formula [1]. [ka] In general formula [1], Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl groups consisting of three or more rings, or substituted or unsubstituted heterocyclic groups consisting of three or more rings. Ar1 and Ar2 are represented by different skeletons. When Ar1 and Ar2 are dibenzothiophene and dibenzofuran skeletons, the organic compound has at least one substituent.

[0027] The substituent represented by R is selected from a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, and a cyano group. If there are multiple Rs, they may be the same or different.

[0028] n is an integer between 2 and 5, and m1 through m3 are integers between 0 and 4.

[0029] Furthermore, in general formula [1], it is preferable that among Ar1 and Ar2, Ar1 is a substituted or unsubstituted aryl group consisting of three or more rings, and Ar2 is a substituted or unsubstituted aryl group consisting of three or more rings different from Ar1, or a substituted or unsubstituted heterocyclic group consisting of three or more rings. This is because, as will be described later, it is preferable that the organic compounds according to the present invention have low molecular structural symmetry. It is even more preferable that there is a large difference in electron density between Ar1 and Ar2. This is because it results in low charge symmetry. Therefore, it is even more preferable that one of Ar1 and Ar2 is a substituted or unsubstituted aryl group consisting of three or more rings, and the other is a substituted or unsubstituted heterocyclic group consisting of three or more rings. Specifically, the substituted or unsubstituted aryl group consisting of three or more rings is selected from the triphenylene skeleton, the fluorene skeleton, and the spirobifluorene skeleton. Furthermore, substituted or unsubstituted heterocyclic groups consisting of three or more rings are selected from the dibenzothiophene skeleton, dibenzofuran skeleton, azatriphenylene skeleton, azadibenzothiophene skeleton, or azadibenzofuran skeleton. The azadibenzothiophene skeleton refers to a skeleton in which the dibenzothiophene skeleton has a nitrogen atom. The azadibenzofuran skeleton refers to a skeleton in which the dibenzofuran skeleton has a nitrogen atom. More specifically, substituted or unsubstituted aryl groups consisting of three or more rings are substituent group A below, and substituted or unsubstituted heterocyclic groups consisting of three or more rings are substituent group B. [ka] [ka] [ka] In substituent group A and substituent group B, R 101 ~R 583R is independently selected from hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted silyl groups, and cyano groups. 101 ~R 583 The group is preferably selected from a hydrogen atom, a deuterium atom, a C1-C4 alkyl group, a C6-C18 aryl group, a C5-C15 heterocyclic group, a trimethylsilyl group, a triphenylsilyl group, and a cyano group, and more preferably selected from a hydrogen atom, a phenyl group, and a tert-butyl group. * indicates the bond position to the phenylene group.

[0030] Substituents A are more preferably from group C below. Furthermore, substituent B is more preferably from group D or group E below. This is because the oxygen, sulfur, and nitrogen atoms included in substituent group D have many lone pairs of electrons and are a group of substituents that are more electron-rich. As a result, the difference in electron density between Ar1 and Ar2 becomes larger, and the molecular symmetry is further reduced. Also, if Ar1 and Ar2 have nitrogen atoms, the HOMO and LUMO become lower (further from the vacuum level), which may disrupt the carrier balance. Furthermore, if a nitrogen atom is present in the fused ring, the fused ring tends to become more nucleophilic, which may reduce the device lifetime. Therefore, it is particularly preferable that Ar1 and Ar2 do not contain nitrogen atoms. Specifically, of Ar1 and Ar2, one is a triphenylene skeleton and the other is a dibenzothiophene skeleton or a dibenzofuran skeleton. More specifically, it is particularly preferable that one of Ar1 and Ar2 is from group C below and the other is from group D below. [ka] [ka] [ka] In substituent group C to substituent group E, R 701 ~R 868 R is independently selected from hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted silyl groups, and cyano groups. 701 ~R 868 The group is preferably selected from a hydrogen atom, a deuterium atom, a C1-C4 alkyl group, a C6-C18 aryl group, a C5-C15 heterocyclic group, a trimethylsilyl group, a triphenylsilyl group, and a cyano group, and more preferably selected from a hydrogen atom, a phenyl group, and a tert-butyl group. * indicates the bond position to the phenylene group.

[0031] Organic compounds represented by general formula (1) have the following characteristics.

[0032] (1-1) Having a phenylene chain with four or more benzene rings bonded to it results in a high glass transition temperature (Tg) and excellent thermal stability of the film.

[0033] (1-2) The benzene rings that make up the phenylene chain are bonded at the meta (m) position, resulting in a high triplet (T1) energy.

[0034] (1-3) Because the structures of Ar1 and Ar2 attached to the phenylene chain are different, the molecule has low symmetry and does not easily aggregate in the membrane.

[0035] Because it has the structure of (1-4)(1-1) to (1-3), it has excellent sublimation properties.

[0036] The following describes these features.

[0037] (1-1) Having a phenylene chain with four or more benzene rings bonded to it results in a high glass transition temperature (Tg) and excellent thermal stability of the film.

[0038] In inventing the organic compound according to the present invention, the inventors focused on the structure of the phenylene chain.

[0039] Specifically, the organic compound according to the present invention has a phenylene chain in which four or more benzene rings are bonded. Therefore, the molecular weight of the compound itself is large, resulting in a high Tg. As a result, the organic compound according to the present invention exhibits excellent thermal stability of the film.

[0040] Table 1 shows the Tg of exemplary compounds A3 and A4, which are embodiments of one embodiment of the present invention, and the Tg of comparative compound 1-A. The Tg of each compound was evaluated by differential scanning calorimetry (DSC). Approximately 2 mg of the sample was sealed in an aluminum pan and rapidly cooled from a high temperature above its melting point. After the sample was made amorphous, the Tg was measured by increasing the temperature at a heating rate of 10°C / min. A DSC 204 F1 manufactured by NETZSCH was used as the measuring instrument. [Table 1] In Table 1, the Tg of comparative compound 1-A was 108°C, indicating a low Tg. In other words, comparative compound 1-A is a compound with undesirable thermal stability of the film.

[0041] On the other hand, the Tg values ​​of example compounds A3 and A4 are 136°C and 149°C, respectively, indicating that they are compounds with high Tg values. Therefore, example compounds A3 and A4 are compounds with excellent thermal stability of the film. In other words, when the organic compounds according to the present invention are used in an organic light-emitting element, a film with excellent thermal stability can be formed, thus providing an organic light-emitting element with excellent device lifetime.

[0042] (1-2) The benzene rings that make up the phenylene chain are bonded at the meta (m) position, resulting in a high triplet (T1) energy.

[0043] In inventing the organic compound according to the present invention, the inventors focused on the structure of the phenylene chain.

[0044] Specifically, the organic compound according to the present invention has a high T1 energy because the benzene constituting the phenylene chain is bonded at the meta position.

[0045] Here, Table 2 shows the T1 energies of the exemplary compound A4, which is an embodiment of the present invention, and the comparative compound 1-B. The measurement of the T1 energy was performed by fluorescence (PL) measurement of a diluted toluene solution and a vapor-deposited film at 77 K and an excitation wavelength of 300 nm using Hitachi F-4500. Thereafter, it was calculated from the emission end of the rising edge on the short wavelength side of the emission spectrum obtained by the phosphorescence mode measurement built into the F-4500. The vapor-deposited film sample was measured using a film vapor-deposited on a quartz substrate at a vacuum degree of 5×10 -4 Pa or less. [Table 2] Solution T1 is the T1 energy when each compound is dissolved in toluene, and vapor-deposited film T1 refers to the T1 energy of a film formed by vapor deposition. ΔT1 represents the difference between solution T1 and vapor-deposited film T1.

[0046] From Table 2, it can be seen that the vapor-deposited film T1 of the exemplary compound A4 has a higher T1 energy compared to the vapor-deposited film T1 of the comparative compound 1-B.

[0047] Here, the effect due to the high T1 energy will be explained.

[0048] The phosphorescent light-emitting device is an organic light-emitting device that uses T1 energy for light emission. The light-emitting layer host material and peripheral materials of the organic light-emitting device need to have a T1 energy sufficiently larger than that of the phosphorescent light-emitting material that emits phosphorescence.

[0049] For example, when the light-emitting layer host material does not have a T1 energy sufficiently larger than that of the phosphorescent light-emitting material, sufficient energy transfer cannot occur to the phosphorescent light-emitting material, resulting in a decrease in the light-emitting efficiency.

[0050] Furthermore, if the light-emitting layer host material does not have a sufficiently large T1 energy compared to the phosphorescent material, reverse energy transfer from the phosphorescent material to the host material is more likely to occur. As a result, the host material remains in an unstable triplet state for a longer period, raising concerns about degradation of the host material. Consequently, the device lifespan is reduced, which is undesirable. In other words, it is preferable for the host material to have a sufficiently large T1 energy. As a result, energy transfer from the host material to the phosphorescent material can be promoted, leading to an excellent device lifespan.

[0051] Specifically, in the case of an organic light-emitting element that emits green phosphorescence, it is preferable that the T1 energy of the host material is at least 0.1 eV greater than 2.43 eV (equivalent to a wavelength of 510 nm). In the case of an organic light-emitting element that emits red phosphorescence, it is preferable that the T1 energy of the host material is at least 0.1 eV greater than 2.07 eV (equivalent to a wavelength of 600 nm).

[0052] In Table 2, the vapor-deposited film T1 of example compound A4 is 2.57 eV, making it more preferable than comparative compound 1-B as a host material for organic light-emitting devices that emit green and red phosphorescence.

[0053] Furthermore, as shown in Table 2, the ΔT1 of comparative compound 1-B is larger than that of example compound A4. In other words, comparative compound 1-B is a compound that tends to have a lower T1 energy during film formation. Comparative compound 1-B has a structure in which the benzene rings constituting the phenylene chain are bonded at the para (p) position (the square dotted line in Table 2), so the molecules tend to aggregate in the film. As a result, it is thought that the T1 energy is lower. On the other hand, in example compound A4, all the benzene rings constituting the phenylene chain are bonded at the m position, so the molecules do not aggregate in the film. As a result, it is thought that the T1 energy is higher.

[0054] Here, we will explain the effects of the fact that molecules are less likely to aggregate within the membrane.

[0055] When molecules tend to aggregate, the formation of grain boundaries, trap levels, and quenchers associated with minute crystallization is likely to occur, which is undesirable from the viewpoint of carrier transport capacity and luminescence efficiency. On the other hand, when molecules do not aggregate easily, the formation of grain boundaries, trap levels, and quenchers associated with minute crystallization is less likely to occur, and good carrier transport and highly efficient luminescence characteristics can be maintained. As a result, it is possible to provide an organic light-emitting device with excellent device lifetime and luminescence efficiency.

[0056] Furthermore, as shown in Figure 8, comparative compound 1-B exhibited a greater emission intensity from singlet (S1) energy around 400 nm during phosphorescent mode measurement compared to example compound A4. In other words, comparative compound 1-B has a longer fluorescence lifetime (excitation lifetime) in the S1 state compared to example compound A4. It is thought that comparative compound 1-B has a longer fluorescence lifetime (excitation lifetime) because its molecules overlap easily within the film and its intermolecular interactions are strong. As shown in the equation below, the rate constant of Förster energy transfer is inversely proportional to the fluorescence lifetime (excitation lifetime) of the host material. As a result, using comparative compound 1-B in an organic light-emitting device is undesirable because the luminescence efficiency decreases.

number

[0057] (1-3) Because the structures of Ar1 and Ar2 attached to the phenylene chain are different, the molecule has low symmetry and does not easily aggregate in the membrane.

[0058] In inventing the organic compound according to the present invention, the inventors focused on the structures of Ar1 and Ar2.

[0059] In general formula [1], Ar1 and Ar2 are different skeletons. Therefore, the organic compounds according to the present invention have reduced symmetry in their molecular structure, making them less prone to aggregation in a film.

[0060] Here, we will explain the effect when the molecular structure of a compound has low symmetry.

[0061] The reduced symmetry suppresses molecular packing, where molecules overlap, making them less prone to aggregation. Therefore, the molecules are less likely to crystallize, and it is easier to maintain an amorphous state. Maintaining an amorphous state is advantageous when used in organic light-emitting devices. This is because, even during device operation, the formation of grain boundaries, trap levels, and quenchers associated with minute crystallization is less likely, thus maintaining good carrier transport and highly efficient light emission characteristics. As a result, it is possible to provide organic light-emitting devices with excellent device lifetime and luminous efficiency.

[0062] Furthermore, the low symmetry of the compound's molecular structure suppresses overlapping between molecules, thereby reducing intermolecular interactions. Consequently, a high T1 energy can be maintained even during film formation.

[0063] Table 3 shows the results of comparing the symmetry of example compound A4, which is one embodiment of the present invention, with comparative compounds 1-C and 1-D. [Table 3] When the molecular structure is viewed in a planar plane, comparative compounds 1-C and 1-D, which have the same Ar1 and Ar2 structures, exhibit high symmetry. Specifically, they have a twofold rotation axis on the dotted line in Table 3. On the other hand, example compound A4 does not have a rotation axis in the molecular plane because the Ar1 and Ar2 structures are different. Therefore, example compound A4 has lower symmetry compared to comparative compounds 1-C and 1-D.

[0064] Table 3 shows that the Tg of comparative compound 1-C was 95°C, while the Tg of example compound A4 was 149°C. Therefore, as stated above, example compound A4 is an organic compound with superior thermal stability compared to comparative compound 1-C.

[0065] Furthermore, the ΔT1 values ​​of comparative compounds 1-C and 1-D, which have high molecular structural symmetry, were 0.30 eV and 0.22 eV, respectively. On the other hand, the ΔT1 value of example compound A4, which has low molecular structural symmetry, was 0.18 eV, which was lower than that of comparative compounds 1-C and 1-D. In other words, example compound A4 is a compound in which the T1 energy does not easily decrease when a vapor-deposited film is formed. For this reason, when used in organic light-emitting devices, the organic compounds according to the present invention are preferred because they easily produce a high T1 energy.

[0066] Furthermore, due to their large ΔT1, comparative compounds 1-C and 1-D, which have high molecular structural symmetry, are compounds that tend to aggregate with each other. As mentioned above, compounds that tend to aggregate with each other as host materials are undesirable because they are more likely to form trap levels and quenchers.

[0067] In the organic compound according to the present invention, it is preferable that one of Ar1 and Ar2 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. It is even more preferable that one of Ar1 and Ar2 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heterocyclic group. This is because the difference in electron density becomes larger, and the symmetry of the molecule decreases further. As a result, overlapping between molecules can be further suppressed. Specifically, it is preferable that one of Ar1 and Ar2 is a substituent from group C, and the other is a substituent from group D or E. Also, as mentioned above, it is particularly preferable that Ar1 and Ar2 do not contain nitrogen atoms. Therefore, it is particularly preferable that one of Ar1 and Ar2 is a substituent from group C, and the other is a substituent from group D.

[0068] Because it has the structure of (1-4)(1-1) to (1-3), it has excellent sublimation properties.

[0069] The organic compound according to the present invention has the structures (1-1) to (1-3) described above, and therefore exhibits excellent sublimation properties. Specifically, it has a phenylene chain in which four or more benzenes are bonded at the m position, and Ar1 and Ar2 which have different structures, and therefore exhibits excellent sublimation properties.

[0070] Here, Table 4 shows the results of comparing the sublimation properties of example compound A4, which is one embodiment of the present invention, with comparative compounds 1-B and 1-D.

[0071] Furthermore, to evaluate sublimation properties, the temperature difference (ΔT) between the sublimation temperature and the decomposition temperature is compared. A larger ΔT indicates higher sublimation properties. The decomposition temperature was determined by thermogravimetric / differential thermal analysis (TG / DTA), and the temperature at which the weight loss reached 5% was defined as the decomposition temperature. The sublimation temperature was 1 × 10⁻⁶ -1 Under a vacuum of Pa, the temperature was slowly increased while flowing Ar, and sublimation purification was performed. The temperature at which a sufficient sublimation rate was reached was defined as the sublimation temperature. A sufficient sublimation rate of 0.01 g / min is acceptable. [Table 4] Table 4 shows that the ΔT of example compound A4 is larger than that of comparative compound 1-B. Furthermore, despite having a larger molecular weight, example compound A4 has a larger ΔT than comparative compound 1-D. Therefore, example compound A4 can be said to be a compound with superior sublimation properties compared to comparative compounds 1-B and 1-D.

[0072] This can be explained as follows:

[0073] As described above, example compound A4 has a phenylene chain in which four or more benzenes are bonded at the meta position, so its conjugation length is not easily elongated and molecular overlapping can be suppressed. In addition, because it has Ar1 and Ar2 with different structures, the symmetry of the molecular structure is reduced, which also suppresses molecular overlapping. Therefore, it is a compound with excellent sublimation properties. On the other hand, comparative compound 1-B has a site where the benzene constituting the phenylene chain is bonded at the para position, so its conjugation length is elongated and molecular overlapping is easy. In addition, comparative compound 1-D has Ar1 and Ar2 with the same structure, so its molecular symmetry is high and molecular overlapping is easy. Therefore, it is a compound with undesirable sublimation properties.

[0074] The compound's excellent sublimation properties make it less prone to decomposition during sublimation purification. This translates to high deposition stability in the fabrication of organic light-emitting devices. In other words, it is possible to produce highly pure deposited films and provide organic light-emitting devices with excellent device lifespan.

[0075] Furthermore, the organic compound according to the present invention is preferable if it has the following characteristics, as it can be suitably used in organic light-emitting devices. Note that multiple of the following conditions may be met simultaneously.

[0076] (1-5) In the general formula [1], when Ar1 and Ar2 do not have SP3 carbon atoms, the bond stability is excellent.

[0077] (1-6) In general formula [1], the substituent represented by R is bonded at the m position of the benzene ring constituting the phenylene chain, resulting in excellent bond stability.

[0078] (1-7) In the general formula [1], the fact that n is 3 or 4 makes it difficult for molecules to aggregate in the membrane.

[0079] The following describes these features.

[0080] (1-5) In the general formula [1], when Ar1 and Ar2 do not have SP3 carbon atoms, the bond stability is excellent.

[0081] In the organic compound according to the present invention, it is preferable that Ar1 and Ar2 do not have SP3 carbon atoms. This is because the carbon-carbon bond with SP3 carbon atoms has a low bond energy, making it prone to bond cleavage during operation of the organic light-emitting device. By having no SP3 carbon atoms in Ar1 and Ar2, bond cleavage can be suppressed. Therefore, 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 lifetime, making it preferable. Furthermore, even when Ar1 and Ar2 have substituents, it is preferable that these substituents do not have SP3 carbons. Particularly preferable is that Ar1 and Ar2 do not have substituents.

[0082] (1-6) In general formula [1], the substituent represented by R is bonded at the m position of the benzene ring constituting the phenylene chain, resulting in excellent bond stability.

[0083] In the organic compound according to the present invention, it is preferable that the substituent represented by R is bonded at a substitution position where steric interference with the phenylene chain is minimal. Specifically, it is preferable that the substituent represented by R is bonded at the m position of the benzene ring constituting the phenylene chain. This is because if the substituent represented by R and the phenylene chain interfere due to steric hindrance, the bond distance between the substituent and the phenylene chain increases. As a result, bond stability decreases, and the bond becomes more prone to cleavage.

[0084] Table 5 shows a comparison of the bond distances between the phenylene chain and substituents of exemplary compounds A5 and A22, which are embodiments of one example. In Table 5, 'a' represents the bond site between the phenylene chain and substituent of each exemplary compound compared. [Table 5] Table 5 shows that the bond distance between the phenylene chain and the substituent in example compound A5 was 1.486 Å, while the bond distance between the phenylene chain and the substituent in example compound A22 was 1.497 Å. This is because example compound A22 is more susceptible to steric hindrance from hydrogen atoms compared to example compound A5.

[0085] Therefore, it is preferable that the substituent and the phenylene chain are bonded at a substitution position where steric interference is minimal. Specifically, it is preferable that the substituent is bonded at the m-position of the benzene ring constituting the phenylene chain. Furthermore, it is preferable that the substituent is one that exhibits minimal steric interference. Specifically, it is preferable that the substituent be an aryl group having 6 to 18 carbon atoms or a heterocyclic group having 5 to 9 carbon atoms. In particular, from the viewpoint of bond stability, it is even more preferable that the substituent be a phenyl group or a pyridyl group.

[0086] In general formula [1], when Ar1 and Ar2 are a dibenzofuran skeleton or a dibenzothiophene skeleton, the organic compound according to the present invention has at least one substituent. This is preferable because it further improves the Tg. In particular, it is even more preferable when the substituent is at the m position of the benzene ring constituting the phenylene chain, because the conjugation length is less likely to elongate and it is easier to maintain a high T1. Furthermore, it is preferable that the substituent is a phenyl group. This is because having a phenyl group as a substituent improves the planarity of the molecule and improves the Tg while suppressing molecular aggregation.

[0087] Furthermore, when the organic compound according to the present invention does not have substituents on the phenylene chain, it is preferable because it is less susceptible to interference due to steric hindrance between the substituent and the phenylene chain. Table 6 shows the results of comparing the bond distances of exemplary compound A2 and exemplary compound A5, which are one embodiment of the present invention. In Table 6, b represents the bond that results in the longest bond distance of the compound. [Table 6] Table 6 shows that the maximum bond distance of example compound A2 was 1.488 Å, while the maximum bond distance of example compound A5 was 1.489 Å. Since example compound A2 does not have substituents on the phenylene chain, it is less susceptible to interference due to steric hindrance between substituents and the phenylene chain. Therefore, the maximum bond distance is even smaller, resulting in a compound with particularly excellent bond stability. Accordingly, it is most preferable that the organic compound according to the present invention does not have substituents on the phenylene chain. In other words, it is particularly preferable that m is 0 in general formula [1].

[0088] (1-7) In the general formula [1], the fact that n is 3 or 4 makes it difficult for molecules to aggregate in the membrane.

[0089] In general formula [1], the organic compound according to the present invention is preferable when n is 3 or 4 because the molecules are less likely to aggregate in the membrane. This is because as the number of n increases, the molecular weight of the compound increases and the Tg tends to increase as well. In addition, as the phenylene chain is elongated, the number of conformations of the molecular structure increases, making the molecules less likely to aggregate. In particular, when n is 3 or 4, it is preferable because it is possible to maintain high sublimation properties.

[0090] Specific examples of organic compounds according to the present invention are shown below. However, the present invention is not limited to these. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] Among the example compounds listed above, the example compounds belonging to group A are compounds in which Ar1 and Ar2 do not have SP3 carbons. Because Ar1 and Ar2 do not have SP3 carbons, these compounds are particularly stable among compounds represented by general formula [1]. It is especially preferable when one of Ar1 and Ar2 is a triphenylene skeleton and the other is a dibenzothiophene skeleton, as this increases T1. More preferably, from the viewpoint of bonding stability, it is preferable that the bond is at position 2 of the triphenylene skeleton, or at position 2, 3, or 4 of the dibenzothiophene skeleton.

[0091] Among the example compounds listed above, the example compounds belonging to group B are compounds in which Ar1 and Ar2 have a dibenzofuran skeleton or a dibenzothiophene skeleton. Because Ar1 and Ar2 have oxygen and sulfur atoms, these compounds can enhance charge transportability due to the abundant lone pairs of electrons on these atoms. Therefore, they are compounds that are particularly easy to adjust the carrier balance with. From the viewpoint of bonding stability, it is preferable that the dibenzofuran skeleton or dibenzothiophene skeleton is bonded to the phenylene chain at either the 2nd, 3rd, or 4th position of the dibenzofuran skeleton or dibenzothiophene skeleton.

[0092] Among the exemplary compounds described above, the exemplary compounds belonging to group C are compounds in which at least one of Ar1 and Ar2 contains a fluorene skeleton. These compounds further have a substituent at the 9th position of fluorene. As a result, the substituent is oriented perpendicular to the in-plane direction of the fluorene skeleton, which particularly suppresses the overlapping of fused rings. For this reason, these compounds have particularly excellent sublimation properties. The substituent at the 9th position of fluorene is preferably an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms. In particular, the bulkier the substituent, the greater the effect of suppressing the overlapping of fused rings, so it is even more preferable that the 9th position of fluorene has a phenyl group.

[0093] Among the example compounds listed above, those belonging to group D are compounds in which at least one of Ar1 and Ar2 contains an azine ring. Because these compounds contain a nitrogen atom in the fused ring, their charge transport properties can be enhanced by the lone pair of electrons and high electronegativity of the nitrogen atom. Therefore, they are particularly well-suited for adjusting the carrier balance.

[0094] (2) Organic light-emitting element Next, an organic light-emitting element according to this embodiment will be described.

[0095] A specific element configuration of the organic light-emitting element according to this embodiment is a multilayer element configuration in which electrode layers and organic compound layers shown in (a) to (f) below are sequentially stacked on a substrate. That is, the organic light-emitting element of this embodiment has at least a pair of electrodes, a first electrode and a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode may be an anode and the other a cathode. In any element configuration, the organic compound layer always includes a light-emitting layer having a light-emitting material. (a) Anode / Emitting layer / Negative (b) Anode / Hole transport layer / Emitting layer / Electron transport layer / Antide (c) Anode / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Another (d) Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport layer / Antide (e) Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Antide (f) Anode / Hole transport layer / Electron blocking layer / Emitting layer / Hole blocking layer / Electron transport layer / Cathode

[0096] However, these examples of element configurations are merely very basic configurations, and the element configuration of the organic light-emitting element of the present invention is not limited to these. For example, an insulating layer, an adhesive layer, or an interference layer may be provided at the interface between the electrode and the organic compound layer. Alternatively, the electron transport layer or hole transport layer may have a multilayer structure with two layers having different ionization potentials. The light-emitting layer may have a multilayer structure with two layers each containing different light-emitting materials. That is, a first light-emitting layer that emits a first light and a second light-emitting layer that emits a second light may be provided between the anode and the cathode. By making the first light and the second light different colors, for example, by making the light white when mixed, an organic light-emitting element that emits white light can be created. Many other diverse layer configurations can also be adopted.

[0097] In this embodiment, the method of extracting light output from the light-emitting layer (element configuration) may be a so-called bottom emission method in which light is extracted from the electrode on the substrate side, or a so-called top emission method in which light is extracted from the opposite side of the substrate. Furthermore, a double-sided extraction method in which light is extracted from both the substrate side and the opposite side of the substrate can also be adopted.

[0098] In the device configurations shown in (a) to (f) above, configuration (f) is preferred because it has both an electron blocking layer and a hole blocking layer. In other words, in configuration (f), which has both an electron blocking layer and a hole blocking layer, both hole and electron carriers can be reliably confined within the light-emitting layer, resulting in an organic light-emitting element with no carrier leakage and high light-emitting efficiency.

[0099] The organic light-emitting element according to this embodiment contains an organic compound represented by the above-mentioned general formula [1] in the organic compound layer. Preferably, the organic light-emitting element according to this embodiment contains an organic compound represented by the above-mentioned general formula [1] in the light-emitting layer. However, the present invention is not limited thereto and 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, electron blocking layers, hole transport layers, hole injection layers, hole blocking layers, etc.

[0100] In the organic light-emitting element according to this embodiment, if the organic compound represented by general formula [1] is included in the light-emitting layer, the light-emitting layer may be a layer consisting of the organic compound represented by general formula [1] and a first compound which is another compound. Here, if the light-emitting layer is a layer consisting of the organic compound represented by general formula [1] and another compound, the organic compound according to the present invention may be used as a host (hereinafter also referred to as "host material") or as an assist (hereinafter also referred to as "assist material") for the light-emitting layer. When the organic compound according to the present invention is used as a host material, the first compound may be a guest (hereinafter also referred to as "guest material").

[0101] Here, the host is the compound with the largest mass ratio among the compounds that make up the light-emitting layer. The guest is the compound that has a smaller mass ratio than the host among the compounds that make up the light-emitting layer and is responsible for the primary light emission. The assist material is the compound that has a smaller mass ratio than the host among the compounds that make up the light-emitting layer and assists the light emission of the guest. The assist material is also called the second host. Alternatively, if the guest is considered the first compound, the assist can be called the second compound.

[0102] Furthermore, it is preferable that the host material has a higher LUMO (closer to the vacuum level) than the guest material. This allows electrons supplied to the host in the light-emitting layer to be efficiently transferred to the guest, improving the luminescence efficiency. In addition, when an assist material is used in addition to the host and guest, it is preferable that the host material has a higher LUMO than the assist material (a material whose LUMO is closer to the vacuum level). This allows electrons supplied to the host in the light-emitting layer to be efficiently transferred to the assist material, enabling the assist material to take on the role of exciton recombination. As a result, it becomes possible to efficiently transfer energy to the guest.

[0103] Furthermore, let Sh1 be the lowest singlet excitation energy of the host and Th1 be the lowest triplet excitation energy, while let Sg1 be the lowest singlet excitation energy of the guest and Tg1 be the lowest triplet excitation energy. In this case, it is preferable that Sh1 > Sg1 be satisfied. It is even more preferable that Th1 > Tg1 be satisfied. Moreover, if Sa1 is the energy of S1 of the assisting material and Ta1 is the energy of T1, then it is preferable that Sa1 > Sg1 be satisfied, and it is even more preferable that Ta1 > Tg1 be satisfied. Furthermore, it is even more preferable that Sh1 > Sa1 > Sg1 be satisfied, and it is even more preferable that Th1 > Ta1 > Tg1 be satisfied.

[0104] The inventors conducted various studies and found that when an organic compound represented by general formula [1] is used as a host or assist for the light-emitting layer, and in particular as a host for the light-emitting layer, an organic light-emitting element with excellent luminescence efficiency and durability can be obtained.

[0105] The organic compound according to the present invention is more preferably used in the light-emitting layer of an organic light-emitting device under the following conditions. Note that multiple of the following conditions may be satisfied simultaneously.

[0106] (2-1) The light-emitting layer has excellent thermal stability because it contains an organic compound represented by general formula [1] at a concentration of 30% to 99% by weight relative to the entire light-emitting layer.

[0107] (2-2) The first compound exhibits excellent luminescence efficiency due to having a fused ring structure as a ligand.

[0108] (2-3) The second compound exhibits excellent luminescence efficiency by having at least one of the following structures: a carbazole skeleton, an azine skeleton, or a xanthone skeleton.

[0109] The following describes these features.

[0110] (2-1) The light-emitting layer has excellent thermal stability because it contains an organic compound represented by general formula [1] at a concentration of 30% to 99% by weight relative to the entire light-emitting layer.

[0111] The organic compound according to the present invention is suitable as a host material for a light-emitting layer because it easily maintains an amorphous state. When using the organic compound according to the present invention in a light-emitting layer, it is preferable that the concentration of the organic compound according to the present invention is 30% by weight or more and 99% by weight or less of the entire light-emitting layer. It is preferable that the concentration of the organic compound according to the present invention relative to the entire light-emitting layer is 50% by weight or more and 99% by weight or less, and more preferably 70% by weight or more and 99% by weight or less. Furthermore, since the organic compound according to the present invention is a compound that easily maintains an amorphous state and does not easily crystallize, it is a compound with excellent device lifetime even at a concentration of 99% by weight of the entire light-emitting layer.

[0112] Furthermore, from the viewpoint of improving the thermal stability of the light-emitting layer film, the organic compound according to the present invention may be used as an assisting material. When used as an assisting material, the concentration of the organic compound according to the present invention relative to the entire light-emitting layer can be 30% by mass or more and 50% by mass or less.

[0113] (2-2) The first compound exhibits excellent luminescence efficiency due to having a fused ring structure as a ligand.

[0114] The organic compound according to the present invention is a compound in which one of Ar1 and Ar2 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heterocyclic group. Specifically, it is a compound in which one of Ar1 and Ar2 is a substituted or unsubstituted aryl group composed of three or more rings, and the other is a substituted or unsubstituted heterocyclic group composed of three or more rings. For this reason, it is preferable that the guest material used with the organic compound according to the present invention in the light-emitting layer has a ligand with a fused ring structure. Specifically, it is preferable that the ligand has a more extended π-conjugation structure, and it is even more preferable that it is a compound having a fused ring structure composed of three or more rings. This is because, if the organic compound according to the present invention and the guest material have highly planar structures, the highly planar structures of the organic compound according to the present invention and the guest material can approach each other through interaction. Specifically, at least one of Ar1 or Ar2 of the organic compound according to the present invention and the ligand of the guest material can easily approach each other. For this reason, it can be expected that the intermolecular distance between the organic compound according to the present invention and the guest material will be shortened.

[0115] It is known that the triplet energy used in phosphorescent light-emitting devices is transferred via the Dexter mechanism. In the Dexter mechanism, energy is transferred through contact between molecules. In other words, by shortening the intermolecular distance between the host material and the guest material, energy is efficiently transferred from the host material to the guest material.

[0116] As described above, by using a highly planar compound having a fused ring structure in its ligand as a guest material, the intermolecular distance between the organic compound according to the present invention and the guest material is shortened. Therefore, energy transfer from the organic compound according to the present invention to the guest material by the Dexter mechanism becomes easier. As a result, an organic light-emitting device with high luminescence efficiency can be provided.

[0117] Specifically, the first compound can be represented by the general formula [2].

[0118] Ir(L)q(L')r(L'')s [2] In the general formula [2], L, L', and L'' represent different bidentate ligands.

[0119] q is an integer between 1 and 3, and r and s are integers between 0 and 2, respectively, where q + r + s = 3. When r is 2, multiple L' elements may be the same or different from each other. When s is 2, multiple L'' elements may be the same or different from each other.

[0120] The substructure Ir(L)q is a structure represented by the following general formulas [Ir-1] to [Ir-12]. [ka] In general formulas [Ir-1] to [Ir-12], Ar3 and Ar4 are a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, or a cyano group. Specifically, Ar3 is preferably a deuterium atom, a fluorine atom, a C1 to C6 alkyl group, a C1 to C4 alkoxy group, a C6 to C10 aryl group, an alkyl-substituted silyl group, or a cyano group, and more preferably a methyl group, a tert-butyl group, or a phenyl group.

[0121] X is selected from oxygen atoms, sulfur atoms, C(R1)(R2), or NR3.

[0122] R1 to R3 are independently selected from hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted silyl groups, and cyano groups. R1 and R2 may bond to each other to form a ring. Specifically, R1 to R3 are preferably C1 to C3 alkyl groups or phenyl groups, and more preferably methyl groups.

[0123] p1 and p2 are each integers between 0 and 4.

[0124] More specifically, the first compound is more preferably a ligand containing a triphenylene skeleton, a phenanthrene skeleton, a fluorene skeleton, a benzofluorene skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, a benzoisoquinoline skeleton, or a naphthoisoquinoline skeleton. By using the first compound having at least one of these skeletons as a ligand, the organic compound according to this embodiment can provide an organic light-emitting element with superior luminescence efficiency.

[0125] Specific examples of the first compound according to this embodiment are shown below. However, the present invention is not limited to these. In the following structural formulas, both bonds between the ligand and the iridium atom may be represented by solid lines; in this case, one bond may be a covalent bond and the other a coordinate bond. On the other hand, if solid and dotted lines are mixed, the solid lines may represent covalent bonds and the dotted lines may represent coordinate bonds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] Among the organometallic complexes described above, the exemplary compounds belonging to groups AA and BB are compounds that have at least a phenanthrene skeleton as a ligand in the Ir complex. For this reason, they are compounds with particularly excellent stability.

[0126] Among the organometallic complexes mentioned above, the exemplary compounds belonging to the CC group are compounds that have at least a triphenylene skeleton as a ligand in the Ir complex. For this reason, they are compounds with particularly excellent stability.

[0127] Among the organometallic complexes described above, the exemplary compounds belonging to the DD group are compounds that have at least a dibenzofuran skeleton or a dibenzothiophene skeleton as a ligand in the Ir complex. Therefore, these compounds contain oxygen and sulfur atoms in the fused ring, and the abundant lone pairs of electrons on these atoms can enhance charge transport. For this reason, they are particularly easy to adjust the carrier balance in.

[0128] Among the organometallic complexes described above, the exemplary compounds belonging to the EE, FF, and GG groups are compounds that have at least a benzofluorene skeleton as a ligand for the Ir complex. These compounds also have a substituent at the 9-position of the fluorene ring. Therefore, because the substituent is oriented perpendicular to the in-plane direction of the fluorene ring, overlapping of fused rings can be particularly suppressed. As a result, these compounds exhibit particularly excellent sublimation properties.

[0129] Among the organometallic complexes described above, the exemplary compounds belonging to the HH group are compounds that have at least a benzoisoquinoline skeleton as a ligand in the Ir complex. Because these compounds contain nitrogen atoms in the fused ring, their charge transport properties can be enhanced by the lone pairs of electrons and high electronegativity of these atoms. Therefore, they are compounds that are particularly good at adjusting the carrier balance.

[0130] Among the organometallic complexes described above, the exemplary compounds belonging to Group II are those that have at least a naphthoisoquinoline skeleton as a ligand in the Ir complex. Because these compounds contain nitrogen atoms in the fused ring, their charge transport properties can be enhanced by the lone pairs of electrons and high electronegativity of these atoms. Therefore, they are particularly well-suited for adjusting the carrier balance.

[0131] (2-3) The second compound exhibits excellent luminescence efficiency by having at least one of the following structures: a carbazole skeleton, an azine ring, or a xanthone skeleton.

[0132] The organic compounds according to the present invention have a large band gap when Ar1 and Ar2 have a fused ring structure of three or more rings. Therefore, when the organic compounds according to the present invention are used in the light-emitting layer, the barrier to carrier injection from the surrounding layer may become large.

[0133] Therefore, materials having a carbazole skeleton, an azine ring, or a xanthone skeleton are preferred as assisting materials. This is because these materials have excellent electron-donating and electron-withdrawing properties, making it easier to adjust the HOMO and LUMO and promoting carrier injection from the surrounding layer.

[0134] When these assisting materials are combined with the organic compound according to the present invention, a good carrier balance can be achieved. In other words, by using these assisting materials, the organic compound according to the present invention can provide an organic light-emitting element with superior luminescence efficiency.

[0135] (3) Other compounds The following are examples of other compounds that can be used in the organic light-emitting device of this embodiment.

[0136] For hole injection and transport layers, materials with high hole mobility are preferred to facilitate hole injection from the anode and transport the injected holes to the light-emitting layer. Furthermore, materials with a high glass transition temperature are preferred to suppress film quality degradation such as crystallization within the organic light-emitting element. Examples of low-molecular-weight and high-molecular-weight materials with hole injection and transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. These hole injection and transport materials are also suitable for use in electron blocking layers.

[0137] The following are specific examples of compounds used as hole injection transport materials, but of course, they are not the only ones. [ka] In addition to organometallic complexes represented by the general formula [2], 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.

[0138] The following are some specific examples of compounds used as luminescent materials, but of course, they are not the only ones. [ka] [ka] In addition to the example compounds A through D described above, the host material or assist material included in the light-emitting layer can also be aromatic hydrocarbon compounds or their derivatives, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, and organoberylium complexes.

[0139] In particular, materials having a carbazole skeleton, materials having an azine ring, or materials having a xanthone skeleton are preferred as assisting materials. This is because these materials have high electron-donating and electron-withdrawing properties, making it easy to adjust the HOMO and LUMO. When these assisting materials are combined with the organic compound according to the present invention, a good carrier balance can be achieved.

[0140] 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.

[0141] Furthermore, among the specific examples below, materials having a carbazole skeleton are EM32 to EM38. Materials having an azine ring are EM35 to EM40. Materials having a xanthone skeleton are EM28 and EM30. [ka] 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.

[0142] The following are specific examples of compounds used as electron transport materials, but of course, they are not the only ones. [ka]

[0143] (4) Configuration of organic light-emitting element The following describes the components other than the organic compound layer that constitute the organic light-emitting element of this embodiment.

[0144] 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 cathode. 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.

[0145] [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.

[0146] [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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] [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.

[0153] [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.

[0154] [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.

[0155] [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.

[0156] 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.

[0157] [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.

[0158] 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.

[0159] [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.

[0160] [Organic 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.

[0161] 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.).

[0162] 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.

[0163] 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.

[0164] 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.

[0165] [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.

[0166] 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.

[0167] 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.

[0168] The transistors that make up the pixel circuit are transistors connected to light-emitting elements, such as the first light-emitting element.

[0169] [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.

[0170] 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.

[0171] The distance between subpixels may be 10 μm or less, specifically 8 μm, 7.4 μm, or 6.4 μm.

[0172] 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.

[0173] (5) Applications of the organic light-emitting element according to this embodiment 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.

[0174] 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.

[0175] 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.

[0176] Next, the display device according to this embodiment will be described with reference to the drawings.

[0177] 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).

[0178] 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.

[0179] 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).

[0180] 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.

[0181] 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.

[0182] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0183] 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.

[0184] 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.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] 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.

[0190] 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.

[0191] 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.

[0192] 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 does not need to 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.

[0193] 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.

[0194] 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.

[0195] 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.

[0196] 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.

[0197] 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.

[0198] The imaging device 1100 has an optical unit (not shown). The optical unit has a plurality of lenses and forms an image on an imaging element housed in the housing 1104. The plurality of lenses can adjust the focus by adjusting their relative positions. This operation can also be performed automatically. The imaging device may be called a photoelectric conversion device. The photoelectric conversion device may include, as imaging methods, a method of detecting the difference from a previous image instead of sequential imaging, a method of cutting out from an image that is always recorded, and the like.

[0199] FIG. 3(b) is a schematic diagram showing an example of an electronic device according to the present 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 reaction unit of a touch panel method. The operation unit may be a biometric recognition unit that recognizes a fingerprint and performs unlocking or the like. 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 imaging element. An image captured by the camera function is displayed on the display unit. Examples of the electronic device include a smartphone, a notebook personal computer, and the like.

[0200] FIG. 4 is a schematic diagram showing an example of a display device according to the present embodiment. FIG. 4(a) shows a display device such as a TV monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The light-emitting device according to the present embodiment may be used for the display unit 1302.

[0201] 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 FIG. 4(a). The lower side of the frame 1301 may also serve as the base.

[0202] Further, the frame 1301 and the display unit 1302 may be bent. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0203] FIG. 4(b) is a schematic diagram showing another example of the display device according to the present embodiment. The display device 1310 in FIG. 4(b) is configured to be foldable and is a so-called foldable display device. The display device 1310 includes a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include a light-emitting device according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be a single seamless display device. The first display unit 1311 and the second display unit 1312 can be separated at the bending point. The first display unit 1311 and the second display unit 1312 may display different images, or may display a single image together with the first and second display units.

[0204] FIG. 5(a) is a schematic diagram showing an example of the lighting device according to the present 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 diffusing portion 1405. The light source may include an organic light-emitting element according to the present embodiment. The optical filter may be a filter that improves the color rendering property of the light source. The light diffusing portion can effectively diffuse the light of the light source, such as lighting up, and deliver the light to a wide range. The optical filter and the light diffusing portion may be provided on the light-emitting side of the lighting. If necessary, a cover may be provided on the outermost side.

[0205] The lighting device is, for example, a device for lighting an interior. The lighting device may emit any color from white, warm white, or other colors from blue to red. It may have a dimming circuit for dimming them. The lighting device may include 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 an AC voltage into a DC voltage. Also, white has a color temperature of 4200K and warm white has a color temperature of 5000K. The lighting device may include a color filter.

[0206] In addition, the lighting device according to the present embodiment may include a heat radiating portion. The heat radiating portion releases the heat inside the device to the outside of the device, and examples thereof include a metal with a high specific heat, liquid silicone, etc.

[0207] 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.

[0208] 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.

[0209] 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.

[0210] 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.

[0211] 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.

[0212] 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.

[0213] 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.

[0214] 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.

[0215] 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.

[0216] 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.

[0217] 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.

[0218] 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.

[0219] 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 set lower.

[0220] 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.

[0221] 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.

[0222] 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.

[0223] Figures 7(b) and 7(c) are diagrams showing the exposure light source 28, and are 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 in which the photoreceptor 27 rotates. 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 column and the second column. The first column and the second column are arranged 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.

[0224] As described above, by using the device using the organic light-emitting element according to the present embodiment, it is possible to display with good image quality and stable display even for long-time display.

Example

[0225] Hereinafter, the present invention will be described by way of examples. However, the present invention is not limited thereto.

[0226] [Example 1 (Synthesis of Exemplary Compound A2)]

Chemical formula

[0227] [[ID=XX]] (1) Synthesis of Compound m-3 A 200 ml eggplant flask was charged with the following reagents and solvents. Compound m-1: 4.0 g (11.1 mmol) Compound m-2: 1.7 g (11.1 mmol) Pd(PPh3)4: 0.13 g Toluene: 40 ml Ethanol: 20 ml 2M aqueous sodium carbonate solution: 20 ml Next, the reaction solution was heated under reflux with stirring in a nitrogen stream and stirred for 6 hours. After completion of the reaction, water was added and liquid separation was performed. Then, it was dissolved in chloroform and purified by column chromatography (chloroform: heptane), and recrystallized with toluene / heptane to obtain 3.0 g (yield: 78%) of white solid compound m-3.

[0228] (2) Synthesis of Compound m-5 A 200 ml eggplant flask was charged with the following reagents and solvents. Compound m-3: 2.5 g (7.3 mmol) Compound m-4: 1.8 g (8.0 mmol) Pd(PPh3)4: 0.08 g Toluene: 25 ml Ethanol: 13 ml 2M aqueous sodium carbonate solution: 20 ml Next, the reaction solution was heated under a nitrogen atmosphere and stirred under reflux for 6 hours. After the reaction was complete, water was added and liquid-liquid was separated, then dissolved in chloroform. This was purified by column chromatography (chloroform:heptane), and then recrystallized with toluene / heptane to obtain 4.0 g (yield: 82%) of compound m-5 as a white solid.

[0229] (3) Synthesis of compound A2 The following reagents and solvents were placed in a 200 ml round-bottom flask. Compound m-5: 2.0g (4.5mmol) Compound m-6: 1.4g (5.0mmol) Pd(dba)2: 0.52g Sphos: 0.74g Potassium phosphate: 2.88g Toluene: 100ml H2O: 10ml Next, the reaction solution was heated under a nitrogen atmosphere and stirred under reflux for 6 hours. After the reaction was complete, water was added and liquid-liquid was separated, then dissolved in chloroform. This was purified by column chromatography (chloroform:heptane), and then recrystallized with toluene / heptane to obtain 5.2 g (yield: 74%) of exemplary compound A2 as a white solid.

[0230] The example compound A2 was analyzed by mass spectrometry using MALDI-TOF-MS (Bruker Autoflex LRF).

[0231] [MALDI-TOF-MS] Measured value: m / z = 714 Calculated value: C 54 H 34 S=71

[0232] [Examples 2 to 20 (Synthesis of Exemplary Compounds)] Tables 7-1 to 7-3 show the example compounds shown in Examples 2 to 20, synthesized in the same manner as in Example 1, except that the starting materials m-4 and m-6 were changed. The measured values ​​(m / z) of the mass spectrometry results, measured in the same manner as in Example 1, are also shown. [Table 7-1] [Table 7-2] [Table 7-3]

[0233] [Comparative Examples 1 to 4 (Synthesis of Comparative Compounds)] Table 8 shows the comparative compounds shown in Comparative Examples 1 to 3, synthesized in the same manner as in Example 1, except that the raw materials m-1, m-2, m-4, and m-6 were changed. The measured mass spectrometry results (m / z) obtained in the same manner as in Example 1 are also shown. [Table 8] Furthermore, comparative compound 1-A was synthesized according to the scheme shown below. Mass spectrometry was also performed in the same manner as in Example 1. [ka]

[0234] [MALDI-TOF-MS] Measured value: m / z = 562 Calculated value: C 42 H 26 S=56

[0235] [Example 21] An organic light-emitting device with a bottom-emission structure was fabricated on a substrate, in which an anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, and cathode were sequentially formed.

[0236] First, an ITO film was deposited on a glass substrate, and an ITO electrode (anode) was formed by applying the desired patterning process. At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrode was formed in this way was used as the ITO substrate in the following process. Next, 1.33 × 10 -4Vacuum deposition was performed by resistance heating in a Pa vacuum chamber to continuously deposit the organic compound layer and electrode layer shown in Table 11 onto the ITO substrate. At this time, the electrode area of ​​the opposing electrodes (metal electrode layer, cathode) was 3 mm². 2 I made it so that it would be like that. [Table 9] The characteristics of the obtained organic light-emitting device were measured and evaluated. The maximum emission wavelength of the organic light-emitting device was 522 nm, and the maximum external quantum efficiency (EQE) was 13%.

[0237] Furthermore, the current density is 100 mA / cm². 2 A continuous operation test was conducted, and the time it took for the brightness degradation rate to reach 5% was measured. When the time it took for the brightness degradation rate to reach 5% in Comparative Example 1 was set to 1.0, the brightness degradation ratio in this example was 1.4.

[0238] In this embodiment, the measuring device specifically measured the current-voltage characteristics with a Hewlett-Packard 4140B micro-ammeter, and the luminous intensity with a Topcon BM7.

[0239] [Examples 22 to 41, Comparative Examples 5 to 8] In Examples 22 to 41, organic light-emitting devices were fabricated in the same manner as in Example 21, except that the compounds shown in Tables 10-1 and 10-2 were appropriately changed. The characteristics of the obtained organic light-emitting devices were measured and evaluated in the same manner as in Example 21. The measurement results are shown in Table 10. [Table 10-1] [Table 10-2] Tables 10-1 and 10-2 show that the EQE of Comparative Examples 5 to 8 were 10%, 8%, 10%, and 8%, respectively. The brightness degradation ratios of Comparative Examples 5 to 8 were 1.0, 0.7, 0.7, and 0.9, respectively. Comparative Compound 1-A's low Tg is thought to be the reason for its poor film stability. Comparative Compound 1-B's low T1 energy and long excitation lifetime are thought to be the reasons for its poor film stability. Comparative Compound 1-C's low Tg is thought to be the reason for its poor film stability. Comparative Compound 1-D's low T1 energy and low sublimation properties are thought to be the reasons for its poor film stability. Furthermore, film stability refers to the resistance to changes in film quality during the operation of the organic light-emitting device. In other words, poor film stability means that the film quality is easily altered during the operation of the organic light-emitting device.

[0240] On the other hand, the organic light-emitting element according to the present invention exhibited excellent luminous efficiency and excellent device lifetime. This is because the exemplary compound according to the present invention has a high T1 energy and a high Tg.

[0241] Furthermore, by selecting a light-emitting material having a condensed ring consisting of three or more rings as a ligand, which is suitable for combination with the organic compound of the present invention, we were able to obtain an organic light-emitting element that is particularly excellent in terms of luminous efficiency and device lifetime.

[0242] Based on the above, by using the organic compound according to the present invention, it is possible to provide an organic light-emitting element with excellent luminescence efficiency and device lifetime.

[0243] [Example 42] An organic light-emitting element was fabricated in the same manner as in Example 21, except that the organic compound layer and electrode layer shown in Table 11 were continuously fabricated. [Table 11] The characteristics of the obtained organic light-emitting element were measured and evaluated. The emission color of the organic light-emitting element was green, and the EQE was 19%.

[0244] [Examples 43 to 67] In Examples 43 to 67, organic light-emitting devices were fabricated in the same manner as in Example 42, except that the compounds shown in Tables 12-1 and 12-2 were appropriately changed. The characteristics of the obtained organic light-emitting devices were measured and evaluated in the same manner as in Example 42. The measurement results are shown in Table 12. [Table 12-1] [Table 12-2] Tables 12-1 and 12-2 show that the luminous efficiency of the organic light-emitting element was improved by using the organic compound according to the present invention as an assist material suitable for combinations with the organic compound according to the present invention. When a compound having at least one of the following as the assist material was used, the luminous efficiency of the organic light-emitting element was excellent. Furthermore, the organic light-emitting elements used in Examples 42 to 67 all showed excellent brightness degradation ratios equivalent to or better than those of Examples 21 to 41.

[0245] Based on the above, the organic compound according to the present invention is an organic compound with excellent thermal stability and sublimation properties of the film. Furthermore, it is an organic compound whose molecules do not easily aggregate. For this reason, by using the organic compound according to the present invention in an organic light-emitting device, an organic light-emitting device with good luminescence characteristics and device life can be obtained.

[0246] Furthermore, the present invention can also take the following configuration.

[0247] (Composition 1) An organic compound characterized by being represented by the following general formula [1]. [ka] In general formula [1], Ar1 and Ar2 are independently selected from substituted or unsubstituted aryl groups consisting of three or more rings, or substituted or unsubstituted heterocyclic groups consisting of three or more rings. Ar1 and Ar2 are represented by different skeletons. When Ar1 and Ar2 are dibenzothiophene skeletons or dibenzofuran skeletons, the organic compound has at least one substituent. The substituent represented by R is independently selected from deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted silyl groups, and cyano groups. If there are multiple Rs, the multiple Rs may be the same or different. n is an integer from 2 to 5, and m1 to m3 are integers from 0 to 4.

[0248] (Configuration 2) The organic compound according to configuration 1, characterized in that, in general formula [1], of Ar1 and Ar2, Ar1 is the aryl group and Ar2 is a different aryl group or heterocyclic group from Ar1.

[0249] (Composition 3) The organic compound according to configuration 2, characterized in that, in general formula [1], of Ar1 and Ar2, Ar1 is the aryl group and Ar2 is the heterocyclic group.

[0250] (Composition 4) The organic compound according to configuration 3, characterized in that, in general formula [1], Ar1 is selected from substituent group A and Ar2 is selected from substituent group B. [ka] [ka] [ka] In substituent group A and substituent group B, R 101 ~R 583 The group is independently selected from hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted silyl groups, and cyano groups. * indicates the bond position to the phenylene group.

[0251] (Composition 5) The organic compound according to configuration 4, characterized in that, in general formula [1], Ar1 is selected from the substituent group C and Ar2 is selected from the substituent group D among Ar1 and Ar2. [ka] [ka] In substituent group C and substituent group D, R 701 ~R 731 The group is independently selected from hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted silyl groups, and cyano groups. * indicates the bond position to the phenylene group.

[0252] (Composition 6) In substituent group A to substituent group D, R 101 ~R 868 The organic compound according to configuration 4 or 5, characterized in that is selected from a hydrogen atom, a deuterium atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 5 to 15 carbon atoms, a trimethylsilyl group, a triphenylsilyl group, and a cyano group.

[0253] (Composition 7) In substituent group A to substituent group D, R 101 ~R868 The organic compound according to configuration 6, characterized in that it is selected from a hydrogen atom, a phenyl group, and a tert-butyl group.

[0254] (Composition 8) An organic compound according to any one of constructs 1 to 7, characterized in that, in the general formula [1], R is an aryl group having 6 to 18 carbon atoms or a heterocyclic group having 5 to 9 carbon atoms.

[0255] (Composition 9) The organic compound according to composition 8, characterized in that R is a phenyl group or a pyridyl group in the general formula [1].

[0256] (Composition 10) An organic compound according to any one of the constructs 1 to 9, characterized in that n is 3 or 4 in the general formula [1].

[0257] (Composition 11) An organic compound according to any one of the configurations 1 to 10, characterized in that m is 0 in the general formula [1].

[0258] (Composition 12) 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 any one of the components 1 to 11.

[0259] (Composition 13) The aforementioned organic compound layer has a light-emitting layer, The organic light-emitting element according to configuration 12, characterized in that the light-emitting layer has the organic compound.

[0260] (Composition 14) The light-emitting layer further comprises the first compound, The organic light-emitting element according to configuration 13, characterized in that the lowest singlet excitation energy of the organic compound is higher than the lowest triplet excitation energy of the first compound.

[0261] (Composition 15) The organic light-emitting element according to configuration 14, characterized in that the first compound has a fused ring structure of at least three rings.

[0262] (Composition 16) The organic light-emitting element according to configuration 15, characterized in that the first compound has a structure represented by the general formula [Ir-1] to [Ir-12]. [ka] In general formulas [Ir-1] to [Ir-12], Ar3 and Ar4 are a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, or a cyano group. X is selected from an oxygen atom, a sulfur atom, C(R1)(R2), or NR3. 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 alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, or a cyano group. p1 and p2 are integers from 0 to 4, and q is an integer from 1 to 3.

[0263] (Composition 17) The organic light-emitting element according to configuration 16, characterized in that the first compound has one of the following skeletons: triphenylene skeleton, phenanthrene skeleton, fluorene skeleton, benzofluorene skeleton, dibenzofuran skeleton, dibenzothiophene skeleton, benzoisoquinoline skeleton, or naphthoisoquinoline skeleton.

[0264] (Composition 18) The light-emitting layer further comprises a second compound, The organic light-emitting element according to any one of configurations 14 to 17, characterized in that the lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the first compound.

[0265] (Composition 19) The organic light-emitting element according to configuration 18, characterized in that the second compound has at least one skeleton selected from a carbazole skeleton, an azine ring, or a xanthone skeleton.

[0266] (Composition 20) 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 12 to 19 and a transistor connected to the organic light-emitting element.

[0267] (Composition 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 the configurations 12 to 19.

[0268] (Composition 22) An electronic device comprising: a display unit having an organic light-emitting element as described in any one of the configurations 12 to 19; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

[0269] (Composition 23) A lighting device characterized by comprising a light source having an organic light-emitting element as described in any one of the configurations 12 to 19, and a light-diffusing part or optical film that transmits light emitted by the light source.

[0270] (Composition 24) A mobile body characterized by comprising a lamp having an organic light-emitting element as described in any one of the configurations 12 to 19, and a body on which the lamp is provided.

[0271] (Composition 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 the configurations 12 to 19. [Explanation of Symbols]

[0272] Single-layer insulating layer 2 reflective electrode 3. Insulating layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color Filters 10 subpixels 11 circuit boards 12 Insulating layer 13 gates 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrodes 18 Thin-film transistors 19 Insulating film 20 contact holes 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting diodes 100 display device 1000 display devices 1001 Top 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 cabinet 1200 Electronic equipment 1201 Display section 1202 Operation unit 1203 enclosure 1300 display device 1301 Picture frame 1302 Display section 1303 Base 1310 Display device 1311 First display section 1312 Second display section 1313 cabinet 1314 Inflection point 1400 Lighting devices 1401 cabinet 1402 Light source 1403 Circuit board 1404 Optical Film 1405 Light Diffusion Section 1500 cars 1501 Taillight 1502 Window 1503 Body 1600 Smart Glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart Glasses 1611 Lens 1612 Control device

Claims

1. An organic compound characterized by being represented by the following general formula [1]. 【Chemical 1】 In the general formula [1], Ar １ and Ar ２ Among them, Ar1 is selected from the group of substituent A, and Ar2 is selected from the group of substituent B. n is an integer from 2 to 5, and m １ to m ３ are each 0. 【Chemical 2】 【Chemical Formula 3】 [Chemical Formula 4] In the substituent A group and the substituent B group, R101 to R583 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, and a cyano group. * represents the bonding position to the phenylene group.

2. In the general formula [1], Ar １ and Ar ２ Among them, Ar １ is a group of substituent C, and Ar ２ is a group of substituent D, and the organic compound according to claim 1, characterized in that it is selected from the group of substituent D. 【Chemical Formula 5】 [[Chemical Formula 6]] In the substituent C group and the substituent D group, R ７０１ to R ７３１ is independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, and a cyano group. * represents the bonding position to the phenylene group.

3. In the group of substituents A to the group of substituents D, R １０１ to R ８６８ is selected from a hydrogen atom, a deuterium atom, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heterocyclic group having 5 to 15 carbon atoms, a trimethylsilyl group, a triphenylsilyl group, and a cyano group. The organic compound according to claim 1 or 2, characterized in that.

4. In the group of substituent A to the group of substituent D, R １０１ to R ８６８ is selected from a hydrogen atom, a phenyl group, and a tert-butyl group, and the organic compound according to claim 3, characterized in that.

5. The organic compound according to claim 1, wherein in the general formula [1], n is 3 or 4.

6. A first electrode and a second electrode, An organic light-emitting device having an organic compound layer disposed between the first electrode and the second electrode, wherein The organic compound layer contains the organic compound according to claim 1.

7. The organic compound layer has a light-emitting layer, The light-emitting layer has the organic compound, and the organic light-emitting device according to claim 6.

8. The light-emitting layer further has a first compound, The lowest excited singlet energy of the organic compound is higher than the lowest excited triplet energy of the first compound, and the organic light-emitting device according to claim 7.

9. The first compound has a condensed ring structure of at least 3 rings or more, and the organic light-emitting device according to claim 8.

10. The first compound has a structure represented by general formulas [Ir-1] to [Ir-12], and the organic light-emitting device according to claim 9. 【Chemical Formula 7】 In general formulas [Ir-1] to [Ir-12], Ar ３ and Ar ４ are a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, or a cyano group. X is selected from an oxygen atom, a sulfur atom, C(R １ )(R ２ ), or NR ３ . 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 alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted silyl group, or a cyano group. p １ and p ２ are each an integer from 0 to 4, and q is an integer from 1 to 3.

11. The first compound has any one of a triphenylene skeleton, a phenanthrene skeleton, a fluorene skeleton, a benzofluorene skeleton, a dibenzofuran skeleton, a dibenzothiophene skeleton, a benzoisoquinoline skeleton, or a naphthoisoquinoline skeleton, and the organic light-emitting device according to claim 10.

12. The light-emitting layer further has a second compound, The lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the first compound, and the organic light-emitting device according to claim 8.

13. The organic light-emitting device according to claim 12, wherein the second compound has at least one skeleton selected from a carbazole skeleton, an azine ring, or a xanthone skeleton.

14. A display device, comprising a plurality of pixels, wherein at least one of the plurality of pixels includes the organic light-emitting device according to any one of claims 6 to 13 and a transistor connected to the organic light-emitting device.

15. An optoelectronic conversion device, comprising an optical unit having a plurality of lenses, an imaging element that receives light that has passed through the optical unit, and a display unit that displays an image captured by the imaging element, wherein the display unit includes the organic light-emitting device according to any one of claims 6 to 13.

16. An electronic device, comprising a display unit including the organic light-emitting device according to any one of claims 6 to 13, a housing in which the display unit is provided, and a communication unit provided in the housing and communicating with the outside.

17. A lighting device, comprising a light source including the organic light-emitting device according to any one of claims 6 to 13 and a light diffusing unit or an optical film that transmits light emitted by the light source.

18. A moving body, comprising a lighting fixture including the organic light-emitting device according to any one of claims 6 to 13 and a body in which the lighting fixture is provided.

19. An image forming apparatus, comprising a photoreceptor and an exposure light source that exposes the photoreceptor, wherein the exposure light source includes the organic light-emitting device according to any one of claims 6 to 13.

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