Organic compound, organic light-emitting element, display device, photoelectric conversion device, electronic device, lighting device, and exposure light source

Abstract

The present invention relates to an organic compound, an organic light emitting element, a display device, a photoelectric conversion device, an electronic device, a lighting device and an exposure light source. An organic compound represented by the following general formula [1] is provided. m L' n wherein L and L' represent different bidentate ligands, the partial structure IrL represents a partial structure represented by the general formula [A-1] or [A-2], and the partial structure IrL' represents a partial structure represented by the general formula [B-1] or [B-2]. #imgabs0#

Description

Technical Field

[0001] The present disclosure relates to an organic compound, an organic light-emitting element, a display device, a photoelectric conversion device, an electronic device, a lighting device, a moving object, and an exposure light source. Background Art

[0002] An organic light-emitting element (hereinafter sometimes referred to as an "organic electroluminescent element" or "organic EL element") is an electronic device comprising a pair of electrodes and an organic compound layer between the electrodes. Electrons and holes are injected from the pair of electrodes to generate excitons of a light-emitting organic compound in the organic compound layer. When the excitons return to their ground state, the organic light-emitting element emits light.

[0003] With the recent remarkable progress in organic light-emitting elements, it is possible to realize light-emitting devices that feature low driving voltage, various emission wavelengths, high-speed responsiveness, and thinness and weight reduction.

[0004] The development of light-emitting organic compounds has been actively pursued because the development of compounds with good light-emitting properties is important for high-performance organic light-emitting devices.

[0005] As compounds developed so far, US Patent Application Publication No. 2010 / 0327736 (PTL 1) discloses the following compound 1-a.

[0006]

[0007] It has been found that compound 1-a described in PTL 1 has room for improvement in light-emitting properties. An organic light-emitting element having higher light-emitting efficiency is desired. Summary of the Invention

[0008] In view of such circumstances, the present disclosure provides an organic compound having good light-emitting properties. The present disclosure also provides an organic light-emitting element having good light-emitting properties.

[0009] The organic compound according to one aspect of the present disclosure is represented by the following general formula [1]:

[0010] Ir L m L' n [1]

[0011] wherein Ir represents iridium. L and L' represent different bidentate ligands. m represents an integer in the range of 1 to 3, and when m is 1, n is 2, when m is 2, n is 1, and when m is 3, n is 0. The partial structure IrL represents a partial structure represented by the following general formula [A-1] or [A-2], and the partial structure IrL' represents a partial structure represented by the following general formula [B-1] or [B-2]. When m is 2 or more, the multiple L's may be the same or different. When n is 2, the multiple L's may be the same or different.

[0012]

[0013]

[0014] Y1 to Y in the general formulas [A-1], [A-2] and [B-2] 24 are independently selected from carbon atoms and nitrogen atoms. 24 When Y1 to Y 24 When two or more of represent carbon atoms having a substituent R, the substituent R may have the same or different structures.

[0015] The substituent R represents a substituent independently selected from 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 silyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0016] When Y1 to Y 24 When any two adjacent carbon atoms simultaneously represent carbon atoms and have a substituent R, the substituent R may be combined to form a ring. The ring structure is a benzene ring, a naphthalene ring, an azine ring, a thiophene ring or a furan ring.

[0017] Z1 and Z2 in the general formulae [A-1] and [A-2] are independently selected from oxygen atoms, sulfur atoms, SiR1R2, CR1R2, GeR1R2, NR1 and CR1=CR2. R1 and R2 may be bonded together to form a ring.

[0018] R1 to R5 in the general formulae [A-1], [A-2] and [B-1] are independently selected from a halogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0019] Further features of the present disclosure will become apparent from the following description of exemplary embodiments with reference to the attached drawings. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1A is a schematic cross-sectional view of an example of a pixel of a display device according to an embodiment of the present disclosure.

[0021] Figure 1B is a schematic cross-sectional view of an example of a display device including an organic light emitting element according to an embodiment of the present disclosure.

[0022] Figure 2 is a schematic diagram of an example of a display device according to an embodiment of the present disclosure.

[0023] Figure 3A is a schematic diagram of an example of an imaging apparatus according to an embodiment of the present disclosure.

[0024] Figure 3B is a schematic diagram of an example of a mobile device according to an embodiment of the present disclosure.

[0025] Figure 4A is a schematic diagram of an example of a display device according to an embodiment of the present disclosure.

[0026] Figure 4B is a schematic diagram of an example of a foldable display device according to an embodiment of the present disclosure.

[0027] Figure 5A is a schematic diagram of an example of a lighting device according to an embodiment of the present disclosure.

[0028] Figure 5B A schematic diagram of a car which is an example of a moving object according to an embodiment of the present disclosure.

[0029] Figure 6A is a schematic diagram of an example of a wearable device according to an embodiment of the present disclosure.

[0030] Figure 6B Schematic diagram of an example of a wearable device according to an embodiment of the present disclosure having a camera device.

[0031] Figure 7 is a schematic diagram of an example of an image forming apparatus according to an embodiment of the present disclosure.

[0032] FIG. 8 is a schematic diagram of an example of an exposure light source of the image forming apparatus according to an embodiment of the present disclosure.

[0033] Figure 9 Schematic diagram of the structures of exemplary and comparative compounds and the symmetry of the ligands.

[0034] Figure 10 Schematic diagram of the structures of exemplary and comparative compounds and the symmetry of the ligands.

[0035] Figure 11Schematic diagram of the structures of exemplary and comparative compounds and the three-dimensional structure of the ligand. DETAILED DESCRIPTION

[0036] <<Organic Compounds>>

[0037] First, the organic compound according to the present embodiment is described below.

[0038] The organic compound according to the present embodiment is an organic compound represented by the following general formula [1]. The organic compound may also be called an organometallic complex because an organic ligand coordinates to a metal.

[0039] Ir L m L' n [1] In the general formula [1], Ir represents iridium. L and L' represent different bidentate ligands. m represents an integer in the range of 1 to 3, when m is 1, n is 2, when m is 2, n is 1, and when m is 3, n is 0. The partial structure IrL represents a partial structure represented by the following general formula [A-1] or [A-2], and the partial structure IrL' represents a partial structure represented by the following general formula [B-1] or [B-2]. When m is 2 or more, multiple L's may be the same or different. When n is 2, multiple L's may be the same or different.

[0040]

[0041] Y1 to Y in the general formulas [A-1], [A-2] and [B-2] 24 are independently selected from carbon atoms and nitrogen atoms. 24 When Y1 to Y 24 When two or more of represent carbon atoms having a substituent R, the substituent R may have the same or different structures.

[0042] The substituent R represents a substituent independently selected from 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 silyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0043] When Y1 to Y 24 When any two adjacent carbon atoms simultaneously represent carbon atoms and have a substituent R, the substituent R may be combined to form a ring. The ring structure is a benzene ring, a naphthalene ring, an azine ring, a thiophene ring or a furan ring.

[0044] Z1 and Z2 in the general formulae [A-1] and [A-2] are independently selected from oxygen atoms, sulfur atoms, SiR1R2, CR1R2, GeR1R2, NR1 and CR1=CR2. R1 and R2 may be bonded together to form a ring.

[0045] R1 to R5 in the general formulae [A-1], [A-2] and [B-1] are independently selected from a halogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0046] In the organic compound according to the present embodiment, the partial structure IrL in the general formula [1] may be a partial structure represented by one of the following general formulas [A-11] to [A-14] and [A-21] to [A-24].

[0047]

[0048] X1 to X2 in the general formulas [A-11] to [A-14] and [A-21] to [A-24] 68 are independently selected from carbon atoms and nitrogen atoms. 68 When X1 to X 68 When two or more of represent carbon atoms having a substituent R, the substituent R may have the same or different structures.

[0049] The substituent R represents a substituent independently selected from 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 silyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0050] When X1 to X2 in the general formulas [A-11] to [A-14] and [A-21] to [A-24] 68 When any two adjacent carbon atoms simultaneously represent carbon atoms and have a substituent R, the substituent R may be combined to form a ring. The ring structure is a benzene ring, a naphthalene ring, an azine ring, a thiophene ring or a furan ring.

[0051] R6 to R9 in the general formulae [A-11] and [A-21] are independently selected from a halogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0052] When Y1 to Y 24 represents a carbon atom, an optional substituent R of the carbon atom, and when X1 to X 68When representing a carbon atom, the optional substituent R of the carbon atom may represent a substituent independently selected from a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted amino group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 3 to 27 carbon atoms.

[0053] R1 to R5 in the general formulas [A-1], [A-2] and [B-1] can be independently selected from a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0054] R6 to R9 in the general formulae [A-11] and [A-21] may be independently selected from a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group, and a substituted or unsubstituted heterocyclic group.

[0055] As when Y1 to Y 24 represents a carbon atom, and optionally a substituent R of the carbon atom and when X1 to X 68 When representing a carbon atom, the optional halogen atom of the optional substituent R of the carbon atom and the halogen atom in R1 to R5 may be, but not limited to, fluorine, chlorine, bromine or iodine.

[0056] As when Y1 to Y 24 represents a carbon atom, and optionally a substituent R of the carbon atom and when X1 to X 68 When representing a carbon atom, the optional alkyl group of the optional substituent R of the carbon atom and the alkyl group in R1 to R5 can be, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, octyl, cyclohexyl, 1-adamantyl or 2-adamantyl.

[0057] As when Y1 to Y 24 represents a carbon atom, and optionally a substituent R of the carbon atom and when X1 to X 68 The optional alkoxy group of the optional substituent R of the carbon atom when representing a carbon atom may be, but is not limited to, methoxy, ethoxy, propoxy, 2-ethyl-octyloxy or benzyloxy.

[0058] As when Y1 to Y 24 represents a carbon atom, and optionally a substituent R of the carbon atom and when X1 to X 68The optional amino group of the optional substituent R of the carbon atom when it represents a carbon atom can be, but is not limited to, N-methylamino, N-ethylamino, N,N-dimethylamino, N,N-diethylamino, N-methyl-N-ethylamino, N-benzylamino, N-methyl-N-benzylamino, N,N-dibenzylamino, anilino, N,N-diphenylamino, N,N-dinaphthylamino, N,N-difluorenylamino, N-phenyl-N-tolylamino, N,N-ditolylamino, N-methyl-N-phenylamino, N,N-dianisolylamino, N-mesityl-N-phenylamino, N,N-bis-mesitylamino, N-phenyl-N-(4-tert-butylphenyl)amino, N-phenyl-N-(4-trifluoromethylphenyl)amino or N-piperidinyl.

[0059] As when Y1 to Y 24 represents a carbon atom, and optionally a substituent R of the carbon atom and when X1 to X 68 The optional aryloxy and heteroaryloxy groups of the optional substituents R of the carbon atom when representing a carbon atom may be, but are not limited to, phenoxy or thienyloxy.

[0060] As when Y1 to Y 24 represents a carbon atom, and optionally a substituent R of the carbon atom and when X1 to X 68 When representing a carbon atom, the optional silyl group of the optional substituent R of the carbon atom may be, but is not limited to, a trimethylsilyl group or a triphenylsilyl group.

[0061] As when Y1 to Y 24 represents a carbon atom, and optionally a substituent R of the carbon atom and when X1 to X 68 When representing a carbon atom, the optional aromatic hydrocarbon group of the optional substituent R of the carbon atom and the aromatic hydrocarbon group in R1 to R5 may be, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, fluoranthenyl or triphenylenyl.

[0062] As when Y1 to Y 24 represents a carbon atom, and optionally a substituent R of the carbon atom and when X1 to X 68 When representing a carbon atom, the optional heterocyclic group of the optional substituent R of the carbon atom and the heterocyclic group in R1 to R5 can be, but are not limited to, pyridyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, phenanthrolinyl, dibenzofuranyl or dibenzothiophenyl.

[0063] Additional optional substituents for the alkyl, alkoxy, amino, aryloxy, silyl, aromatic hydrocarbon and heterocyclic groups may be, but are not limited to, a halogen atom such as fluorine, chlorine, bromine or iodine; an alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl or tert-butyl; an alkoxy group such as methoxy, ethoxy or propoxy; an amino group such as dimethylamino, diethylamino, dibenzylamino, diphenylamino or ditolylamino; an aryloxy group such as phenoxy; an aromatic hydrocarbon group such as phenyl or biphenyl; a heterocyclic group such as pyridyl or pyrrolyl; or a cyano group.

[0064] Methods for synthesizing organic compounds

[0065] Next, a method for synthesizing the organic compound according to the present embodiment is described. For example, the organic compound according to the present embodiment is synthesized according to the following reaction scheme.

[0066]

[0067]

[0068]

[0069] Various compounds can be produced by appropriately changing the compounds represented by (a), (b), (f), (h), (j), (k), (n), (p), (q) and (r). The present disclosure is not limited to the above synthesis schemes and the compounds synthesized by the above synthesis schemes, and various synthesis schemes and reagents can be used. The synthesis method is described in detail in the exemplary embodiments.

[0070] Characteristics of the organic compound according to the present embodiment

[0071] Next, the characteristics of the organic compound according to this embodiment will be described. In the organic compound according to this embodiment, the partial structure IrL is a partial structure represented by the general formula [A-1] or [A-2]. Therefore, it can also be said that the ligand L has a dibenzo[f,h]quinoline skeleton.

[0072] The organic compound according to this embodiment has the following properties and characteristically has a high quantum yield. The organic compound according to this embodiment also has high sublimation properties. In addition, the organic compound can be used to provide an organic light-emitting element with high luminous efficiency. In addition, the organic compound can be used to provide an organic light-emitting element with high durability.

[0073] (1) The quantum yield is high because the ligand has a dibenzo[f,h]quinoline skeleton with a ring structure bridged by Z1 or Z2.

[0074] (2) Since the ligand has a ring structure in which a dibenzo[f,h]quinoline skeleton is bridged by Z1 or Z2, the ligand has low symmetry and high sublimability.

[0075] These characteristics are described below with reference to Comparative Compound 1-b as a comparison object. Comparative Compound 1-b is a compound in which the auxiliary ligand of Compound 1-a described in PTL 1 is changed from acetylacetone to phenylpyridine.

[0076] (1) The quantum yield is high because the ligand has a dibenzo[f,h]quinoline skeleton with a ring structure bridged by Z1 or Z2.

[0077] In developing organic compounds according to the present disclosure, the inventors focused on the structure of the organic compound's ligand. More specifically, in an Ir complex having a ligand with a dibenzo[f,h]quinoline skeleton, the dibenzo[f,h]quinoline skeleton of the ligand is bridged by Z1 or Z2 to form a ring structure and improve quantum yield.

[0078] Table 1 shows the comparative results of the luminescence characteristics of exemplary compound A21 and comparative compound 1-b as organic compounds according to the present embodiment. The luminescence wavelength was measured in a photoluminescence (PL) measurement of a diluted toluene solution at an excitation wavelength of 350 nm at room temperature using an F-4500 manufactured by Hitachi, Ltd. The quantum yield was determined by measuring the absolute quantum yield of the diluted toluene solution using an absolute PL quantum yield measurement system (C9920-02) manufactured by Hamamatsu Photonics KK. The quantum yield is represented by a value relative to the quantum yield of exemplary compound A21 set to 1.0.

[0079] Table 1

[0080]

[0081] Table 1 shows that exemplary compound A21 has higher quantum yield and better luminescence characteristics than comparative compound 1-b. The present inventors have considered this as follows.

[0082] The structural difference between the two compounds lies in whether the dibenzo[f,h]quinoline structure in the ligand forms a bridged ring structure. More specifically, in comparative compound 1-b, the ligand does not form a ring structure with two bridging carbon atoms within the dibenzo[f,h]quinoline backbone. In contrast, exemplary compound A21 has a ring structure in which two carbon atoms within the dibenzo[f,h]quinoline backbone are bridged by a dimethylmethylene group.

[0083] As represented by the following formula, the photoluminescence quantum yield (PLQY) is calculated from the rate constants of the radiative transition (luminescence) and the non-radiative transition (non-luminescence) from the excited state to the ground state. In the following formula, kr represents the rate constant of the radiative transition (radiative decay rate), and knr represents the rate constant of the non-radiative transition (non-radiative decay rate). As represented by the following formula, the radiative decay rate (kr) is proportional to the square of the transition dipole moment (TDM) (see Phys. Chem. Chem. Phys. 16, 1719-1758 (2014)).

[0084]

[0085]

[0086] ΔE: Energy difference between T1 and S0

[0087] h: Planck constant

[0088] c: speed of light

[0089] This formula shows that increasing the radiative decay rate (kr) is effective in increasing the photoluminescence quantum yield PLQY. As described above, since the radiative decay rate (kr) is proportional to the square of the transition dipole moment, increasing the transition dipole moment is effective.

[0090] The transition dipole moment in an Ir complex is proportional to the degree of charge transfer (CT) between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) (see J. Phys. Chem. 94, 239-243 (1990)). In Ir complexes, the HOMO is distributed in the aromatic ring that is σ-bound to the Ir metal, and the LUMO is distributed in the heterocyclic ring that is coordinated to the Ir metal. For example, in the representative Ir complex Ir(ppy)3, it is known that the HOMO is distributed in the benzene ring and the LUMO is distributed in the pyridine ring.

[0091] The present inventors have discovered that in Ir complexes containing ligands having a dibenzo[f,h]quinoline skeleton, bridging atoms in the dibenzo[f,h]quinoline skeleton to form a ring structure can improve the CT properties between the aromatic and heterocyclic rings. More specifically, they discovered that the CT properties can be improved by bridging the six-atom aromatic or heterocyclic ring in the dibenzo[f,h]quinoline skeleton, including the atoms that bind to the Ir metal, at positions corresponding to the para position relative to the Ir metal. More specifically, they discovered that the CT properties can be improved by bridging the 9- or 4-position of the dibenzo[f,h]quinoline skeleton. As a result, the transition dipole moment can be increased, and the photoluminescence quantum yield (PLQY) can be improved.

[0092] like Figure 9 As shown in , in exemplary compound A21, an aromatic ring composed of six atoms, including a carbon atom bonded to the Ir metal σ, has a bridged structure via a methylene chain (dimethylmethylene) at the position corresponding to the para position to the Ir metal. The electron-donating alkyl group in the aromatic ring in which the HOMO is distributed increases electron-donating ability, causes charge polarization, and improves CT properties.

[0093] In exemplary compound G1, a six-atom heterocyclic ring, including a nitrogen atom coordinated to the Ir metal, has a bridged structure via an oxygen atom at the para position relative to the Ir metal. The electronegative oxygen atoms in the heterocyclic ring, where the LUMO is distributed, enhance electron-withdrawing ability, causing charge polarization and improving CT properties.

[0094] While structures having aromatic rings bridged by electron-donating substituents and structures having heterocyclic rings bridged by electron-withdrawing substituents are exemplified, the present disclosure is not limited to these structures. More specifically, regardless of whether the substituents constituting the bridged structure are electron-donating or electron-withdrawing, the partial structure IrL represented by the general formula [A-1] or [A-2] can disrupt symmetry and induce charge polarization in the aromatic ring or heterocyclic ring. This improves CT properties, increases the transition dipole moment, and increases the radiative decay rate (kr). This is likely to result in an improved photoluminescence quantum yield (PLQY).

[0095] On the other hand, the ligand having a dibenzo[f,h]quinoline skeleton in Comparative Compound 1-b has higher symmetry and less charge polarization than the organic compound according to this embodiment, which is likely to result in poor CT properties, low transition dipole moment, and low quantum yield.

[0096] The above formula also shows that reducing the radiationless decay rate (knr) is also effective in improving the photoluminescence quantum yield (PLQY).

[0097] Nonradiative transitions (nonradiative deactivation) are deactivation processes caused by the conversion of excited-state energy into molecular vibrational modes. Nonradiative transitions can be reduced by reducing molecular vibrations. Molecular vibrations can be effectively reduced by increasing molecular rigidity. This is because molecules with high rigidity have fewer stretching, rotational, and bending vibrations in their bonds.

[0098] In the organic compound according to this embodiment, the ligand has a structure having a bridging atom in the dibenzo[f,h]quinoline skeleton. Therefore, the ligand has less vibration and improved rigidity compared to a simple dibenzo[f,h]quinoline ligand without a bridging structure. Therefore, it is believed that the ligand has a smaller non-radiative decay rate (knr) and a higher photoluminescence quantum yield (PLQY) than a ligand without a bridging structure.

[0099] (2) Since the ligand has a dibenzo[f,h]quinoline skeleton with a ring structure bridged by Z1 or Z2, the ligand has low symmetry and high sublimability.

[0100] In the development of organic compounds according to the present disclosure, the inventors focused on the structural symmetry of the ligands. For a brief discussion of the structural symmetry of the ligands, as Figure 10 As shown in the figure, the molecular structure of the ligand is compared by assuming that the nitrogen atom is a carbon atom. The ligand of the comparative compound 1-b has a triple axis perpendicular to the molecular plane and three double axes parallel to the molecular plane (by Figure 10 In contrast, the exemplary compound A21 has a high symmetry due to its bridged structure and only one two-fold axis parallel to the molecular plane (shown by Figure 10 ) and has lower symmetry than comparative compound 1-b.

[0101] The symmetry of the ligand can be reduced to lower the sublimation temperature. This is because, in the case of a ligand with lower symmetry, the organic compound is less likely to aggregate. In contrast, in the case of a ligand with higher symmetry, the organic compound is more likely to aggregate, resulting in a high sublimation temperature. A low sublimation temperature can result in a larger difference between the sublimation temperature and the thermal decomposition temperature, less thermal decomposition during sublimation, and higher sublimability.

[0102] Figure 10 The results of the comparison of sublimation properties of exemplary compound A21 and comparative compound 1-b, which are organic compounds according to the present embodiment, are shown. For the evaluation of sublimation properties, the difference between the sublimation temperature and the decomposition temperature is compared. A higher temperature difference indicates higher sublimation properties. The decomposition temperature is the temperature at which the weight loss reaches 5% in TG / DTA measurement. The sublimation temperature is the temperature at which the weight loss reaches 5% in 1×10 -1 The temperature at which a sufficient sublimation rate is achieved when sublimation purification is performed by slowly raising the temperature in an Ar flow under a vacuum degree of 100 Pa.

[0103] Figure 10Exemplary Compound A21, an organic compound according to this embodiment, is shown to be a material having a large difference between its sublimation temperature and its decomposition temperature and high sublimability. Furthermore, due to its high sublimability, sublimation purification can be performed stably without decomposition. This also demonstrates high vapor deposition stability in the production of organic light-emitting devices. More specifically, a high-purity vapor-deposited film can be formed without decomposition during vapor deposition, and a long-life organic light-emitting device can be provided.

[0104] Low symmetry also provides the following advantages. Comparative compound 1-b has a ligand with an extended π conjugated system in a dibenzo[f,h]quinoline structure. Therefore, the organic compound easily aggregates with the help of π-π interactions, which promotes concentration quenching in the organic light-emitting element. On the other hand, although the ligand has a dibenzo[f,h]quinoline skeleton, the organic compound according to this embodiment has lower symmetry due to the bridge structure. Compared with compounds without a bridge structure, this can reduce π-π interactions and reduce the aggregation of organic compounds. Therefore, a high-efficiency organic light-emitting element with less concentration quenching can be provided.

[0105] The evaluation of the characteristics (1) and (2) of the organic compound according to the present embodiment is described in more detail in the exemplary embodiments described later.

[0106] Next, other characteristics of the organic compound having the partial structure IrL represented by any one of the general formulas [A-11] to [A-14] and [A-21] to [A-24] are described. These organic compounds have the following characteristics and are therefore suitable for use in organic light-emitting elements.

[0107] (3) When Z1 or Z2 in the general formula [A-1] or [A-2] is any one of SiR1R2, CR1R2 and GeR1R2, the substituent extending in the direction perpendicular to the in-plane direction of the dibenzo[f,h]quinoline structure further improves the sublimation property.

[0108] (4) When Z1 or Z2 in the general formula [A-1] or [A-2] is an oxygen atom or a sulfur atom, the lone pair of electrons of the oxygen atom or the sulfur atom improves the CT property and further improves the quantum yield.

[0109] (5) When the partial structure IrL is represented by the general formula [A-14] or [A-24], the ligand has high chemical stability because the carbon atoms constituting the basic skeleton of the ligand are composed only of sp2 carbon atoms.

[0110] These characteristics are described below.

[0111] (3) When Z1 or Z2 in the general formula [A-1] or [A-2] is any one of SiR1R2, CR1R2 and GeR1R2, the substituent extending in the direction perpendicular to the in-plane direction of the dibenzo[f,h]quinoline structure further improves the sublimation property.

[0112] As shown in the general formula [A-1] or [A-2], the organic compound according to this embodiment has a highly planar ligand having a dibenzo[f,h]quinoline skeleton as a basic skeleton and an extended π-conjugated system. The bridged structure reduces the symmetry of the ligand and inhibits ligand stacking. When Z1 or Z2 is any of SiR1R2, CR1R2, and GeR1R2, the substituents R1 and R2 can reduce the planarity of the ligand and further inhibit ligand stacking.

[0113] The planarity of the ligands of exemplary compound A21 and comparative compound 1-b was compared. Figure 11 As shown in , in exemplary compound A21, the ligand has a bridged structure via a dimethylmethylene group, and the substituent (methyl) bonded to the methylene chain extends in a direction perpendicular to the plane of the ligand. Therefore, the steric hindrance of the substituent makes it difficult for the ligand to aggregate and can further reduce the aggregation of the organic compound. This can further reduce the sublimation temperature and further improve the sublimation property. Therefore, the organic compound can have a higher resistance to concentration quenching.

[0114] Specifically, Z1 or Z2 in the general formula [A-1] or [A-2] may be CR1R2. In other words, the partial structure IrL may be represented by the general formula [A-11] or [A-21].

[0115] (4) When Z1 or Z2 in the general formula [A-1] or [A-2] is an oxygen atom or a sulfur atom, the lone pair of electrons of the oxygen atom or the sulfur atom improves the CT property and further improves the quantum yield.

[0116] When Z1 or Z2 in the general formula [A-1] or [A-2] is an oxygen atom or a sulfur atom, the organic compound according to this embodiment has a structure in which the carbon atoms in the dibenzo[f,h]quinoline skeleton are bridged by oxygen atoms or sulfur atoms. Oxygen atoms have high electronegativity and abundant lone pairs of electrons, and sulfur atoms have abundant lone pairs of electrons. Therefore, the oxygen or sulfur atom of Z1 or Z2 enhances polarization in the ligand, increases the amount of change in electron density, and can further improve CT properties. As a result, as shown in Table 2, the organic compound has a higher quantum yield. The quantum yield is measured as described above and is represented by a value relative to the quantum yield of exemplary compound A21, which is set to 1.0.

[0117] Table 2

[0118]

[0119] Therefore, from the viewpoint of quantum yield, Z1 or Z2 in the general formula [A-1] or [A-2] may be an oxygen atom or a sulfur atom. In other words, the partial structure IrL may be represented by any of the general formulas [A-12], [A-13], [A-22], and [A-23].

[0120] (5) When the partial structure IrL is represented by the general formula [A-14] or [A-24], the ligand has high chemical stability because the carbon atoms constituting the basic skeleton of the ligand are composed only of sp2 carbon atoms.

[0121] When the partial structure IrL is represented by the general formula [A-14] or [A-24], the organic compound according to this embodiment has a structure in which the carbon atoms in the dibenzo[f,h]quinoline skeleton are bridged by ethylene chains. Such a structure can improve the chemical stability of the ligand of the organic compound. This is because the carbon atoms constituting the basic skeleton of the ligand are composed only of sp2 carbon atoms. In other words, the carbon atoms constituting the basic skeleton of the ligand L can be composed only of sp2 carbon atoms. The basic skeleton of the ligand in this specification refers to Y1 to Y2 in the general formula [A-1] or [A-2]. 16 All structures are carbon atoms with hydrogen atoms.

[0122] In an organic light-emitting element, redox cycles repeatedly occur while the element is driven, and the element contains high-energy molecules in an excited state. Therefore, the molecules that make up the element can be stable against redox and have a structure consisting only of high-energy bonds that do not break even in a high-energy state.

[0123] When the partial structure IrL is represented by the general formula [A-14] or [A-24], the carbon atoms constituting the basic skeleton of the ligand are composed only of sp2 carbon atoms. Therefore, when the organic compound is used in an organic light-emitting element, the organic light-emitting element can have particularly high driving durability. When X in the general formula [A-14] is 25 To X 34 and X in the general formula [A-24] 59 To X 68 When at least one of the atoms is a nitrogen atom, the bonds constituting the basic skeleton of the ligand are composed only of sp2 hybrid orbitals, as with carbon atoms. Therefore, the ligand has a basic skeleton composed of bonds with sufficiently high bond energy and thus has high chemical stability.

[0124] Examples of organic compounds according to this embodiment

[0125] Specific examples of the organic compound according to the present embodiment are described below. However, the present disclosure is not limited to these examples.

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] Among the exemplary compounds, exemplary compounds (A1 to A40) belonging to Group A are organic compounds represented by the general formula [A-1] in which Z1 represents CR1R2. In other words, the partial structure IrL of the organic compound is represented by the general formula [A-11]. These compounds have characteristics (1), (2), and (3) and have high sublimation properties among the above-mentioned compounds.

[0149] Among the exemplary compounds, exemplary compounds (B1 to B40) belonging to Group B are organic compounds represented by the general formula [A-1] in which Z1 represents a sulfur atom. In other words, the partial structure IrL of the organic compound is represented by the general formula [A-12]. These compounds have characteristics (1), (2), and (4) and have better luminescence characteristics than the above exemplary compounds.

[0150] Among the exemplary compounds, the exemplary compounds (C1 to C40) belonging to Group C are organic compounds represented by the general formula [A-1] in which Z1 represents an oxygen atom. In other words, the partial structure IrL of the organic compound is represented by the general formula [A-13]. These compounds have characteristics (1), (2), and (4) and have better luminescence characteristics than the above exemplary compounds.

[0151] Among the exemplary compounds, exemplary compounds (D1 to D40) belonging to Group D are organic compounds represented by the general formula [A-1] in which Z1 represents CR1=CR2. In other words, the partial structure IrL of the organic compound is represented by the general formula [A-14]. These compounds have characteristics (1), (2), and (5) and have higher chemical stability than the above exemplary compounds.

[0152] Among the exemplary compounds, exemplary compounds (E1 to E40) belonging to Group E are organic compounds represented by the general formula [A-2] in which Z1 represents CR1R2. In other words, the partial structure IrL of the organic compound is represented by the general formula [A-21]. These compounds have characteristics (1), (2), and (3) and have high sublimation properties among the above-mentioned compounds.

[0153] Among the exemplary compounds, exemplary compounds (F1 to F40) belonging to Group F are organic compounds represented by the general formula [A-2] in which Z1 represents a sulfur atom. In other words, the partial structure IrL of the organic compound is represented by the general formula [A-22]. These compounds have characteristics (1), (2), and (4) and have better luminescence characteristics than the above exemplary compounds.

[0154] Among the exemplary compounds, the exemplary compounds (G1 to G40) belonging to Group G are organic compounds represented by the general formula [A-2] in which Z1 represents an oxygen atom. In other words, the partial structure IrL of the organic compound is represented by the general formula [A-23]. These compounds have characteristics (1), (2), and (4) and have better luminescence characteristics than the above exemplary compounds.

[0155] Among the exemplary compounds, exemplary compounds (H1 to H40) belonging to Group H are organic compounds represented by the general formula [A-2] in which Z1 represents CR1=CR2. In other words, the partial structure IrL of the organic compound is represented by the general formula [A-24]. These compounds have characteristics (1), (2), and (5) and have higher chemical stability than the above exemplary compounds.

[0156] Among the exemplary compounds, exemplary compounds (I1 to I20) belonging to Group I are organic compounds represented by the general formula [A-1] in which Z1 represents SiR1R2. Exemplary compounds (J1 to J20) belonging to Group J are organic compounds represented by the general formula [A-1] in which Z1 represents GeR1R2. These compounds have characteristics (1), (2), and (3) and have high sublimation properties among the above-mentioned compounds.

[0157] Among the exemplary compounds, the exemplary compounds (K1 to K20) belonging to Group K are organic compounds represented by the general formula [A-1] in which Z2 represents NR1. These compounds have a structure in which carbon atoms in a dibenzo[f,h]quinoline skeleton are bridged by nitrogen atoms. Like oxygen atoms and sulfur atoms, nitrogen atoms have lone pairs of electrons and have characteristic (4), thereby obtaining compounds having good CT properties and high quantum yields. In addition, when the substituent (R1) of the nitrogen atom is a bulky substituent such as a benzene ring, the substituent can more effectively reduce the aggregation of ligands due to steric hindrance, so that the compound has higher sublimation properties.

[0158] Among the exemplary compounds, exemplary compounds (L1 to L20) belonging to the L group are organic compounds represented by the general formula [A-2] in which Z2 represents SiR1R2. Exemplary compounds (M1 to M20) belonging to the M group are organic compounds represented by the general formula [A-2] in which Z2 represents GeR1R2. These compounds have characteristics (1), (2), and (3) and have high sublimation properties among the above-mentioned compounds.

[0159] Among the exemplary compounds, the exemplary compounds (N1 to N20) belonging to Group N are organic compounds represented by the general formula [A-2] in which Z2 represents NR1. These compounds have a structure in which carbon atoms in a dibenzo[f,h]quinoline skeleton are bridged by nitrogen atoms. Like oxygen atoms and sulfur atoms, nitrogen atoms have lone pairs of electrons and have characteristic (4), thereby obtaining compounds having good CT properties and high quantum yields. In addition, when the substituent (R1) of the nitrogen atom is a bulky substituent such as a benzene ring, the substituent can more effectively reduce the aggregation of ligands due to steric hindrance, so that the compound has higher sublimation properties.

[0160] In the general formula [1], m is preferably 1 or 2, more preferably 2. In other words, it can be represented by Ir(L)(L')2. In this embodiment, the partial structure IrL is represented by the general formula [A-1] or [A-2], and the ligand L has a high molecular weight and a highly planar structure. Therefore, the organic compound having the ligand L easily associates due to the interaction between the organic compounds and tends to have a higher molecular weight. However, when m=1, the organic compound as a whole can have a smaller molecular weight, have smaller interactions between the organic compounds, and therefore have a lower sublimation temperature. As a result, sublimation purification can be performed at a lower temperature, and elements can be produced by vacuum deposition at a lower temperature.

[0161] In the general formula [A-1] or [A-2], the carbon atom adjacent to the carbon atom σ-bonded to the Ir metal in the aromatic ring may have a methyl group. This improves the balance between the metal-to-ligand charge transfer (MLCT) property of the interaction between the ligand and the Ir metal and the π-π* property of the ligand. This also applies to the general formulas [A-11] to [A-14] and [A-21] to [A-24].

[0162] Therefore, in the general formula [1], the partial structure IrL may be a partial structure represented by the following general formula [C-1] or [C-2].

[0163]

[0164] Furthermore, in the general formula [1], the partial structure IrL may be a partial structure represented by any one of the following general formulae [C-11] to [C-14] and [C-21] to [C-24].

[0165]

[0166] Y2 to Y in the general formulas [C-1] and [C-2] 16 and Y2 to Y in the general formulas [A-1] and [A-2] 16 In addition, X2 to X in the general formulas [C-11] to [C-14] and [C-21] to [C-24] are the same. 68 and X2 to X in the general formulae [A-11] to [A-14] and [A-21] to [A-24] 68 same.

[0167] In addition, in the general formula [1], all three ligands may have different structures. When all three ligands have different structures, the Ir complex as a whole can have lower symmetry, improved sublimation properties, and higher resistance to concentration quenching. In other words, it can be an organic compound represented by the following general formula [2].

[0168] Ir LL'L" [2]

[0169] In the general formula [2], Ir represents iridium. L, L' and L" represent different bidentate ligands. The partial structure IrL represents a partial structure represented by the general formula [A-1] or [A-2], and the partial structure IrL' represents a partial structure represented by the general formula [B-1] or [B-2]. The partial structure IrL" is a partial structure represented by any one of the general formulas [A-1], [A-2], [B-1] and [B-2]. The partial structure IrL" may be a partial structure represented by the general formula [B-1] or [B-2].

[0170] <<Organic Light Emitting Device>>

[0171] Next, the organic light emitting element according to this embodiment is described.

[0172] The specific element structure of the organic light-emitting element according to the present embodiment may be a multilayer element structure including electrode layers and organic compound layers shown in the following (1) to (6) stacked sequentially on a substrate. More specifically, the organic light-emitting element according to the present embodiment includes at least one pair of electrodes (a first electrode and a second electrode) and an organic compound layer between the electrodes. The first electrode may be an anode, and the second electrode may be a cathode. In any element structure, the organic compound layer always includes a light-emitting layer containing a light-emitting material.

[0173] (1) Anode / light-emitting layer / cathode

[0174] (2) Anode / Hole Transport Layer / Emitting Layer / Electron Transport Layer / Cathode

[0175] (3) Anode / Hole Transport Layer / Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0176] (4) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0177] (5) Anode / Hole Injection Layer / Hole Transport Layer / Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0178] (6) Anode / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0179] These element structure examples are only basic element structures, and the element structure of the organic light-emitting element disclosed herein is not limited to these element structures. 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. The electron transport layer or the hole transport layer may have a multilayer structure having two layers with different ionization potentials. The light-emitting layer may have a multilayer structure having two layers each containing a different light-emitting material. Therefore, a first light-emitting layer for emitting a first light and a second light-emitting layer for emitting a second light may be provided between the anode and the cathode. An organic light-emitting element for emitting white light may be produced in which the white light is composed of a first light and a second light of different colors. In addition to such a structure, various other layer structures may also be used.

[0180] In this embodiment, the mode (element form) for extracting light from the light-emitting layer can be a bottom emission mode in which light is extracted from the electrode on the substrate side, or a top emission mode in which light is extracted from the side opposite to the substrate side. This mode can also be a double-sided extraction mode in which light is extracted from both the substrate side and the side opposite to the substrate side.

[0181] Among the element structures shown in (1) to (6), structure (6) has both an electron blocking layer (electron blocking layer) and a hole blocking layer (hole blocking layer). Therefore, the electron blocking layer and the hole blocking layer in (6) can reliably confine both hole and electron carriers within the light-emitting layer. As a result, the organic light-emitting element does not have carrier leakage and has high luminous efficiency.

[0182] The organic light-emitting element according to this embodiment contains an organic compound represented by the general formula [1] in the organic compound layer. The organic light-emitting element according to this embodiment may contain an organic compound represented by the general formula [1] in the light-emitting layer. However, the present disclosure is not limited thereto, and it can be used as a constituent material of an organic compound layer other than the light-emitting layer of the organic light-emitting element according to this embodiment. More specifically, it can be used as a constituent material of an electron transport layer, an electron injection layer, an electron blocking layer, a hole transport layer, a hole injection layer, or a hole blocking layer.

[0183] In the organic light-emitting element according to the present embodiment, when the light-emitting layer contains an organic compound represented by the general formula [1], the light-emitting layer can be a layer consisting only of the organic compound represented by the general formula [1]. Alternatively, the light-emitting layer can be a layer consisting of the organic compound represented by the general formula [1] and another compound. When the organic compound represented by the general formula [1] is used as a guest (hereinafter also referred to as a guest material), the light-emitting layer can contain a first compound. The light-emitting layer can further contain a second compound. The first compound can be a host (hereinafter also referred to as a host material). The second compound can be an auxiliary agent (hereinafter also referred to as an auxiliary material). For the light-emitting layer consisting of the organic compound represented by the general formula [1] and another compound, the organic compound according to the present embodiment can be used as the host or guest of the light-emitting layer. The organic compound can also be used as an auxiliary material that can be contained in the light-emitting layer.

[0184] The host is the compound with the highest mass ratio among the compounds constituting the light-emitting layer. The guest is a compound with a lower mass ratio than the host among the compounds constituting the light-emitting layer and serves as the primary light-emitting compound. The auxiliary material is a compound with a lower mass ratio than the host among the compounds constituting the light-emitting layer and assists the guest in luminescence. The auxiliary material is also called a secondary host.

[0185] The host can be a material having a higher LUMO than the guest (a material having a LUMO closer to the vacuum level). This allows the electrons supplied to the host of the light-emitting layer to be efficiently delivered to the guest and improves the luminous efficiency. In addition, when an auxiliary material is used in addition to the host and the guest, the host can be a material having a higher LUMO than the auxiliary material (a material having a LUMO closer to the vacuum level). This allows the electrons supplied to the host of the light-emitting layer to be efficiently delivered to the auxiliary material, and the auxiliary material can play a role in exciton recombination. This enables efficient energy transfer to the guest.

[0186] The energy of the excited singlet state (S1) of the host (singlet energy) is given by S h1 The energy of the excited triplet state (T1) (triplet energy) is expressed by T h1 Indicates that the energy of the object S1 is determined by S g1 Represented by T1, and the energy of the object is represented by T g1 Then, S can be satisfied. h1 >S g1 . It can also satisfy T h1 >T g1 In addition, the energy S1 of the auxiliary material a1 and the energy T of T1 a1 Can satisfy S a1 >S g1 and T a1 >T g1In addition, S h1 >S a1 >S g1 , and can also satisfy T h1 >T a1 >T g1 .

[0187] The present inventors conducted various studies and found that when an organic compound represented by the general formula [1] is used as a host or guest in a light-emitting layer, particularly as a guest in a light-emitting layer, an organic light-emitting element having high light-emitting efficiency and durability can be produced.

[0188] When the organic light-emitting element according to this embodiment contains an organic compound represented by the general formula [1] in the light-emitting layer, the compound contained in the light-emitting layer satisfies the following conditions. Two or more of the following conditions may be satisfied simultaneously. As described above, the organic compound represented by the general formula [1] may be used as a guest in the light-emitting layer, and under each of the following conditions, the second organic compound may be a host in the light-emitting layer.

[0189] (7) The light-emitting layer contains the organic compound represented by the general formula [1] at a concentration within a range of 1% by mass to 30% by mass of the entire light-emitting layer.

[0190] (8) The light-emitting layer contains an organic compound represented by the general formula [1] and a structure selected from the group consisting of a triphenylene structure, a phenanthrene structure, A second organic compound having at least one structure selected from the group consisting of a fluoranthene structure and a fluoranthene structure.

[0191] (9) The light-emitting layer contains the organic compound represented by the general formula [1] and a second organic compound having a carbazole structure.

[0192] (10) The light-emitting layer contains the organic compound represented by the general formula [1] and a second organic compound having at least one of a dibenzothiophene structure and a dibenzofuran structure.

[0193] (11) The light-emitting layer contains the organic compound represented by the general formula [1] and a second organic compound having no sp3 carbon.

[0194] Each condition is described below.

[0195] (7) The light-emitting layer contains the organic compound represented by the general formula [1] at a concentration within a range of 1% by mass to 30% by mass of the entire light-emitting layer.

[0196] When the organic compound represented by the general formula [1] is used in the light-emitting layer, the amount of the organic compound is preferably in the range of 1% to 30% by mass of the entire light-emitting layer. In addition, the amount of the organic compound is more preferably in the range of 5% to 15% by mass of the entire light-emitting layer. When the organic compound represented by the general formula [1] is used in the light-emitting layer, the lower the concentration, the better the characteristics can be obtained. A low concentration can obtain a light-emitting element with high efficiency and color purity.

[0197] This is due to the structural characteristics of the organic compound represented by the general formula [1]. The organic compound represented by the general formula [1] has a ligand L having an extended π conjugated system. Therefore, when the organic compound represented by the general formula [1] is mixed in the light-emitting layer at an excessively high concentration, the organic compound may aggregate and cause concentration quenching, thereby reducing the luminous efficiency. On the other hand, the organic compound represented by the general formula [1] at a relatively low concentration in the range of 1% by mass to 30% by mass of the entire light-emitting layer is less likely to aggregate and can improve the luminous efficiency.

[0198] (8) The light-emitting layer contains an organic compound represented by the general formula [1] and a structure selected from the group consisting of a triphenylene structure, a phenanthrene structure, A second organic compound having at least one structure selected from the group consisting of a fluoranthene structure and a fluoranthene structure.

[0199] In the organic compound represented by the general formula [1], the ligand has a dibenzo[f,h]quinoline skeleton and a highly planar structure having an extended π conjugated system. Therefore, the second organic compound used in combination with the organic compound represented by the general formula [1] can have an aromatic ring and a highly planar structure. This is because the highly planar portion of the second organic compound having a highly planar structure can interact with and approach the highly planar portion of the organic compound represented by the general formula [1]. More specifically, the ligand L of the organic compound represented by the general formula [1] easily approaches the planar portion of the second organic compound. Therefore, it can be expected that the intermolecular distance between the organic compound represented by the general formula [1] and the second organic compound can be shortened.

[0200] It is known that triplet energy for phosphorescence in organic light-emitting devices is transferred via the Dexter mechanism. The Dexter mechanism involves energy transfer via intermolecular contact. More specifically, the intermolecular distance between a host and a guest is shortened to facilitate efficient energy transfer from the host to the guest.

[0201] The use of a highly planar organic compound as the second organic compound shortens the intermolecular distance between the organic compound represented by the general formula [1] and the second organic compound, leading to more efficient energy transfer between the two compounds via the Dexter mechanism. More specifically, the use of the second organic compound as a host improves the efficiency of energy transfer from the second organic compound to the organic compound represented by the general formula [1]. As a result, an organic light-emitting element that emits light with high efficiency can be provided.

[0202] The highly planar structure specifically refers to triphenylene structure, phenanthrene structure, A compound having at least one of these structures used as a second organic compound in combination with the organic compound represented by the general formula [1] can provide a light-emitting element with higher efficiency.

[0203] (9) The light-emitting layer contains the organic compound represented by the general formula [1] and a second organic compound having a carbazole structure.

[0204] As shown in Table 3 below, the organic compound represented by the general formula [1] has a HOMO site consisting of the Ir metal and an aromatic ring, and a LUMO site consisting of the Ir metal and a heterocyclic ring. In Table 3 below, the HOMO site and the LUMO site are surrounded by dotted circles. In Table 3, the portion surrounded by dotted squares represents an unoccupied orbital. Therefore, an orbital exists after the HOMO site is located near the Ir metal and the benzene ring bound to the Ir metal. Therefore, the organic compound represented by the general formula [1] tends to have a low hole transport ability due to this unoccupied orbital.

[0205] Therefore, the present inventors have discovered that an organic compound represented by the general formula [1] can be used in combination with an organic compound having a carbazole structure. The carbazole structure is a heterocyclic ring having a high hole-transporting ability. Therefore, the organic compound having a carbazole structure has a high hole-transporting ability. Therefore, it is expected that the combined use of an organic compound having a carbazole structure can compensate for the reduced hole-transporting ability of the organic compound represented by the general formula [1] and improve the hole-transporting ability of the light-emitting layer.

[0206] Furthermore, the organic compound represented by the general formula [1] can be used in combination with a second organic compound having a carbazole structure and an azine ring. For example, an azine ring such as pyridine, pyrazine, pyrimidine, or triazine is a heterocyclic ring having a high electron transport capacity. Therefore, further introducing an azine ring into an organic compound having a carbazole structure can not only improve the hole transport capacity, but also improve the electron transport capacity. As a result, a light-emitting layer having improved electron transport capacity and hole transport capacity can be formed.

[0207] Table 3

[0208]

[0209] (10) The light-emitting layer contains the organic compound represented by the general formula [1] and a second organic compound having at least one of a dibenzothiophene structure and a dibenzofuran structure.

[0210] Generally, Ir complexes are known as hole-trapping compounds. In addition, as described above, the organic compound represented by the general formula [1] has an empty orbital and therefore has a particularly low hole-transporting ability.

[0211] In order to improve the hole transporting ability, the second organic compound used in combination with the organic compound represented by the general formula [1] may be a material having a skeleton with a high hole transporting ability. A skeleton with a high hole transporting ability is a skeleton having abundant lone pairs of electrons and a high electron donating ability. More specifically, it is a skeleton having electron donating nitrogen atoms such as carbazole as described in (9) above, or a skeleton having chalcogen atoms such as a dibenzothiophene structure or a dibenzofuran structure, which are rich in lone pairs of electrons.

[0212] Among them, the second organic compound that can be suitably used in combination with the organic compound represented by the general formula [1] may have a skeleton having at least one of a dibenzothiophene structure and a dibenzofuran structure. A skeleton having a dibenzothiophene structure or a dibenzofuran structure is less likely to have an extremely shallow HOMO, and thus can adjust the carrier balance between holes and electrons, and is suitable for assisting the hole transporting ability of the organic compound represented by the general formula [1]. In particular, the second organic compound may have a dibenzothiophene structure rich in lone pair electrons.

[0213] (11) The light-emitting layer contains the organic compound represented by the general formula [1] and a second organic compound having no sp3 carbon.

[0214] As described in (8) above, shortening the intermolecular distance between the organic compound represented by the general formula [1] and the second organic compound can improve the luminescence characteristics of the organic light-emitting element. Using an organic compound without sp3 carbon as the second organic compound can further shorten the intermolecular distance with the organic compound represented by the general formula [1].

[0215] In the presence of sp3 carbons, the hydrophobic interaction and steric hindrance of the alkyl group increase the intermolecular distance between the organic compound represented by the general formula [1] and the second organic compound. In contrast, in the absence of sp3 carbons and therefore the hydrophobic interaction and steric hindrance of the alkyl group, the effect of increasing the intermolecular distance does not occur, and the intermolecular distance with the organic compound represented by the general formula [1] can be shortened. This can improve the luminescent properties of the organic light-emitting element.

[0216] The following are specific examples of the first compound according to the present embodiment, more specifically, specific examples of compounds suitable for the host material. However, the present disclosure is not limited to these examples.

[0217]

[0218]

[0219]

[0220]

[0221] Among these compounds, exemplary compounds (AA1 to AA21) belonging to the AA group are compounds having a carbazole structure. Therefore, these compounds have a high hole transport capability due to the carbazole structure. This can compensate for the relatively low hole transport capability of the organic compound represented by the general formula [1]. Therefore, a light-emitting layer having a high hole transport capability can be formed, and the organic light-emitting element can have a high luminous efficiency.

[0222] Among these compounds, exemplary compounds belonging to the BB group (BB1 to BB42) are compounds containing a structure selected from the group consisting of triphenylene structure, phenanthrene structure, Compounds having a skeleton of at least one of the group consisting of a fluoranthene structure and a fluoranthene structure and having no sp3 carbon. Therefore, when these compounds are combined with an organic compound represented by the general formula [1] to form a layer, the intermolecular distance between them can be shortened. This allows for efficient intermolecular energy transfer, more specifically, energy transfer from the second organic compound to the compound represented by the general formula [1], and can improve luminous efficiency. Among these compounds, compounds having a triphenylene structure, more specifically BB6 to BB8, BB10 to BB29, and BB34 to BB42, have particularly high planarity.

[0223] Among the above compounds, the exemplary compounds (CC1 to CC21) belonging to the CC group are compounds having a dibenzothiophene structure or a dibenzofuran structure in the skeleton and having no sp3 carbon. Therefore, when these compounds are combined with the organic compound represented by the general formula [1] to form a light-emitting layer, the balance between the HOMO and LUMO is improved. This results in an organic light-emitting element with good carrier balance and high luminous efficiency. Among these compounds, compounds having a dibenzothiophene structure, more specifically CC2 to CC5, CC7, CC9, CC13 to CC16, and CC18 to CC21, produce a good carrier balance.

[0224] Other compounds

[0225] Examples of other compounds that can be used for the organic light-emitting element according to this embodiment are described below.

[0226] The hole injection / transport material suitable for the hole injection layer or the hole transport layer can be a material with a high hole mobility that can promote hole injection from the anode and can transport the injected holes to the light-emitting layer. In addition, a material with a high glass transition temperature can be used to reduce the degradation of film quality such as crystallization in the organic light-emitting element. Examples of low molecular weight materials or high molecular weight materials with hole injection / transport capabilities include, but are not limited to, triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, polyvinylcarbazole, polythiophene, and other conductive polymers. Hole injection / transport materials are also suitable for electron blocking layers.

[0227] Specific examples of the compound that can be used as the hole injecting / transporting material include, but are not limited to, the following compounds.

[0228]

[0229] In addition to the organic compound represented by the general formula [1], examples of luminescent materials mainly related to the luminescent function include fused ring compounds (for example, fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organic aluminum complexes such as tris(8-hydroxyquinoline)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylene vinylene) derivatives, polyfluorene derivatives and polyphenylene derivatives.

[0230] Specific examples of compounds that can be used as the light-emitting material include, but are not limited to, the following compounds.

[0231]

[0232]

[0233] In addition to the materials of the AA group, the BB group, and the CC group, examples of the light-emitting layer main body or auxiliary material in the light-emitting layer include aromatic hydrocarbon compounds and their derivatives, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organic aluminum complexes such as tris(8-hydroxyquinoline)aluminum, and organic beryllium complexes.

[0234] The auxiliary material may be a compound having at least one structure selected from a xanthone structure, a thioxanthone structure, and a benzophenone structure, each having a deep LUMO (low-to-vacuum level) similar to an azine ring. More specifically, the following EM28 to EM31 may be used. The auxiliary material may also be a compound having an azine ring.

[0235] Specific examples of the compound that can be used as a host or an auxiliary material in the light-emitting layer include, but are not limited to, the following compounds.

[0236]

[0237] The electron transporting material can be selected from materials that can transport electrons injected from the cathode to the light-emitting layer and can be selected in consideration of the balance with the hole mobility of the hole transporting material. Examples of materials having electron transporting ability include, but are not limited to, oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, Derivatives and anthracene derivatives). In addition, electron transporting materials are also suitable for use in the hole blocking layer.

[0238] Specific examples of the compound that can be used as the electron transporting material include, but are not limited to, the following compounds.

[0239]

[0240] The following describes the components other than the organic compound layer that make up the organic light-emitting element according to this embodiment. The organic light-emitting element may include a first electrode, an organic compound layer, and a second electrode on a substrate. One of the first electrode and the second electrode is an anode, and the other is a cathode. A protective layer or a color filter may be provided on the second electrode. When a color filter is provided, a planarization layer may be provided between the color filter and the protective layer. The planarization layer may be formed of, for example, an acrylic resin.

[0241] The substrate can be made of quartz, glass, silicon, resin, or metal. The substrate can have switching elements such as transistors and wiring, and an insulating layer can be provided thereon. The insulating layer can be formed of any material, provided that the insulating layer has contact holes to ensure electrical connection between the anode and the wiring and can insulate from unconnected wiring. For example, the insulating layer can be formed of a resin such as polyimide, silicon oxide, or silicon nitride.

[0242] The constituent material of the anode can have a work function as large as possible. Examples of constituent materials include metal elements such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium and tungsten, mixtures thereof, alloys thereof, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide. Conductive polymers such as polyaniline, polypyrrole and polythiophene can also be used. These electrode materials can be used alone or in combination. The anode can be composed of a single layer or multiple layers. When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, alloys thereof or laminates thereof can be used. When used as a transparent electrode, an oxide transparent conductive layer such as indium tin oxide (ITO) or indium zinc oxide can be used. However, the present disclosure is not limited thereto. The anode can be formed by photolithography.

[0243] The constituent material of the cathode can be a material with a small work function. For example, alkali metals such as lithium, alkaline earth metals such as calcium, metal elements such as aluminum, titanium, manganese, silver, lead or chromium, or mixtures thereof can be used. Alloys of these metal elements can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper or zinc-silver can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials can be used alone or in combination. The cathode can be composed of a single layer or multiple layers. Among them, silver can be used, and silver alloys can be used to reduce the aggregation of silver. As long as the aggregation of silver can be reduced, the alloy can have any ratio. For example, it can be 1:1.

[0244] The cathode can be, but is not limited to, an oxide conductive layer such as ITO for top-emitting elements or a reflective electrode such as aluminum (Al) for bottom-emitting elements. The cathode can be formed by any method. DC or AC sputtering can achieve good film coverage and easily reduce resistance.

[0245] A protective layer may be provided after the cathode is formed. For example, a glass sheet with a moisture absorbent may be attached to the cathode to reduce the amount of water, etc. entering the organic compound layer and reduce the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the amount of water, etc. entering the organic compound layer. For example, after the cathode is formed, the cathode is transported to another chamber without breaking the vacuum, and a silicon nitride film having a thickness of 2 μm may be formed as a protective layer by a chemical vapor deposition (CVD) method. The protective layer may be formed by a CVD method and then by an atomic layer deposition (ALD) method.

[0246] In addition, each pixel may be provided with a color filter. For example, a color filter matching the size of the pixel may be provided on another substrate and attached to the substrate of the organic light-emitting element, or the color filter may be patterned using photolithography on a protective layer formed of silicon oxide or the like.

[0247] 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 the present embodiment is formed by the following method. That is, the organic compound layer can be formed by a dry method such as vacuum deposition, ionized deposition, sputtering or plasma. Instead of the dry method, a wet method in which a layer is formed by a known coating method (for example, spin coating, dipping, casting, LB method, inkjet method, etc.) using an appropriate solvent can also be adopted. The layer formed by vacuum deposition or solution coating method etc. hardly undergoes crystallization etc. and has high stability over time. When a film is formed by a coating method, it can also be formed in combination with a suitable binder resin. Examples of binder resins include, but are not limited to, polyvinyl carbazole resins, polycarbonate resins, polyester resins, ABS resins, acrylic resins, polyimide resins, phenolic resins, epoxy resins, silicone resins and urea-formaldehyde resins. The binder resin can be used alone as a homopolymer or a copolymer or can be used in combination. If necessary, additives such as known plasticizers, oxidation inhibitors, and / or ultraviolet absorbers may be used.

[0248] <<Device Including Organic Light-Emitting Element>>

[0249] The organic light emitting element according to this embodiment can be used as a component of a display device or a lighting device. Other uses include exposure light sources for electrophotographic image forming devices, backlights for liquid crystal displays, and light emitting devices having color filters in white light sources.

[0250] The display device may be an image information processing device that includes an image input unit for inputting image information from an area array CCD, a linear array CCD, or a memory card, an information processing unit for processing the input information, and displays the input image on a display unit. The display device may have a plurality of pixels, and at least one of the pixels may include an organic light-emitting element according to this embodiment and a transistor connected to the organic light-emitting element. The substrate may be a semiconductor substrate formed of silicon or the like, and the transistor may be a MOSFET formed on the substrate.

[0251] The display unit of an imaging device or inkjet printer may have a touchscreen function. The driving system of the touchscreen function may be, but is not limited to, an infrared irradiation system, an electrostatic capacitance system, an impedance film system, or an electromagnetic induction system. The display device may also be used in the display unit of a multifunction printer.

[0252] Next, a display device according to the present embodiment is described with reference to the drawings.

[0253] Figure 1A and Figure 1BSchematic cross-sectional view of an example of a display device including an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin film transistor (TFT).

[0254] Figure 1A An example of a pixel used as a component of a display device according to this embodiment is shown. The pixel includes sub-pixels 10. The sub-pixels are 10R, 10G, and 10B, each emitting different colors. The luminescent colors can be differentiated by the wavelength of light emitted from the light-emitting layer, or a color filter or the like can be used to selectively transmit or color-convert the light emitted from each sub-pixel. Each sub-pixel includes a reflective electrode 2 as a first electrode on an interlayer insulating layer 1, an insulating layer 3 covering the ends 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.

[0255] A transistor and / or a capacitor element may be provided below or inside the interlayer insulating layer 1. The transistor may be electrically connected to the first electrode via a contact hole (not shown) or the like.

[0256] The insulating layer 3 is also called a bank or a pixel separation film. The insulating layer 3 covers the end of the first electrode and surrounds the first electrode. The portion of the first electrode not covered with the insulating layer is in contact with the organic compound layer 4 and serves as a light emitting region.

[0257] 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 .

[0258] The second electrode 5 may be a transparent electrode, a reflective electrode or a semi-transparent electrode.

[0259] The protective layer 6 reduces the penetration of moisture into the organic compound layer. The protective layer is shown as a single layer, but may be a plurality of layers. The protective layer may include an inorganic compound layer and an organic compound layer.

[0260] Color filters 7 are divided into 7R, 7G, and 7B according to color. The color filters can be formed on a planarization film (not shown). In addition, a resin protective layer (not shown) can be provided on the color filters. The color filters can be formed on the protective layer 6. Alternatively, the color filters can be attached after being provided on a counter substrate such as a glass substrate.

[0261] Figure 1B The display device 100 shown in FIG. 1 includes an organic light-emitting element 26 and a TFT 18 as an example of a transistor. The display device 100 includes a substrate 11 made of glass, silicon, or the like, and an insulating layer 12 on the substrate 11. An active element such as the TFT 18, as well as a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element are provided on the insulating layer 12.

[0262] The TFT 18 includes a semiconductor layer 15, a drain electrode 16, and a source electrode 17. The TFT 18 is covered with an insulating film 19. An anode 21 constituting an organic light emitting element 26 is connected to the source electrode 17 via a contact hole 20.

[0263] The electrical connection between the electrodes (anode 21 and cathode 23) of the organic light emitting element 26 and the electrodes (source electrode 17 and drain electrode 16) of the TFT is not limited to Figure 1B More specifically, it is only necessary to electrically connect either the anode 21 or the cathode 23 to either the source electrode 17 or the drain electrode 16 of the TFT 18.

[0264] Although the organic compound layer 22 is Figure 1B Although the display device 100 shown in FIG. 1 is a single layer, the organic compound layer 22 may be composed of a plurality of layers. The cathode 23 is covered with a first protective layer 25 and a second protective layer 24 for preventing degradation of the organic light emitting element.

[0265] exist Figure 1B The transistor used as a switching element in the display device 100 shown in FIG. 1 may be replaced with another switching element such as a metal insulator metal (MIM) element.

[0266] Used for Figure 1B The transistors of display device 100 are not limited to thin-film transistors comprising an active layer on an insulating surface of a substrate and may also be transistors comprising a single-crystal silicon wafer. The active layer may be single-crystal silicon, non-single-crystal silicon such as amorphous silicon or microcrystalline silicon, or a non-single-crystal oxide semiconductor such as indium zinc oxide or indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0267] It can be formed in a substrate such as a Si substrate Figure 1B The phrase "formed in a substrate" means that the substrate itself, such as a Si substrate, is processed to form the transistor. Therefore, the transistor in the substrate can be considered to be formed by integrating the substrate and the transistor.

[0268] In the organic light emitting element according to the present embodiment, the luminous brightness is controlled by using a TFT as an example of a switching element. Organic light emitting elements can be arranged in multiple planes to display images at various luminous brightnesses. The switching element according to the present embodiment is not limited to a TFT and can be a transistor formed of low-temperature polycrystalline silicon or an active-matrix driver formed on a substrate such as a Si substrate. "On a substrate" can also be referred to as "in a substrate". Whether a transistor is arranged in a substrate or a TFT is used depends on the size of the display unit. For example, for a display unit of about 0.5 inches, an organic light emitting element can be arranged on a Si substrate.

[0269] Figure 2 1 is a schematic diagram of an example of a display device according to this embodiment. Display device 1000 may include a touch screen 1003, a display panel 1005, a frame 1006, a circuit substrate 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. Touch screen 1003 and display panel 1005 are connected to flexible printed circuits (FPCs) 1002 and 1004, respectively. Transistors are printed on circuit substrate 1007. If the display device is not a mobile device, battery 1008 may not be provided. Even if the display device is a mobile device, battery 1008 may be provided in another location.

[0270] The display device according to this embodiment can be used as a display unit of an imaging device including an optical unit having multiple lenses and an imaging element for receiving light passing through the optical unit. The imaging device can include a display unit for displaying information acquired by the imaging element. The display unit can be a display unit exposed from the outside of the imaging device or a display unit located within a viewfinder. The imaging device can be a digital camera or a digital video camera. The imaging device can also be referred to as a photoelectric conversion device.

[0271] Figure 3A 11 is a schematic diagram of an example of an imaging device according to this embodiment. Imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operating unit 1103, and a housing 1104. Viewfinder 1101 may include a display device according to this embodiment. In such cases, the display device may display environmental information and imaging instructions, as well as the image to be captured. Environmental information may include the intensity of external light, the direction of external light, the speed of the subject, and the possibility that the subject is obscured by an obstruction.

[0272] Since the appropriate imaging opportunity is short, it is desirable to display information as quickly as possible. Therefore, a display device including an organic light-emitting element according to this embodiment can be used. This is because organic light-emitting elements have a high response speed. Display devices including organic light-emitting elements are more suitable for use than these devices and liquid crystal displays, which require high display speeds.

[0273] The imaging device 1100 includes an optical unit (not shown). The optical unit has multiple lenses and focuses an image on an imaging element within a housing 1104. The focus of the lenses can be adjusted by adjusting the relative positions of the lenses. This operation can also be performed automatically.

[0274] The display device according to the present embodiment may include red, green, and blue color filters. In the color filters, red, green, and blue may be arranged in a delta arrangement.

[0275] The display device according to this embodiment can be used as a display unit of an electronic device such as a mobile terminal. Such a display device can have both a display function and an operation function. Examples of mobile terminals include mobile phones such as smartphones, tablet computers, and head-mounted displays.

[0276] Figure 3B 1 is a schematic diagram of an example of an electronic device according to this embodiment. Electronic device 1200 includes a display unit 1201, an operating unit 1202, and a housing 1203. Housing 1203 may include circuitry, a printed circuit board including the circuitry, a battery, and a communication unit. Operating unit 1202 may be a button or a touchscreen response unit. The operating unit may be a biometric recognition unit for fingerprint recognition and unlocking. An electronic device with a communication unit may also be referred to as a communication device.

[0277] Figure 4A and Figure 4B is a schematic diagram of an example of a display device according to this embodiment. Figure 4A 13. A display device such as a TV monitor or a PC monitor is shown. The display device 1300 includes a frame 1301 and a display unit 1302. The light emitting device according to this embodiment can be used for the display unit 1302. The display device 1300 includes a base 1303 for supporting the frame 1301 and the display unit 1302. The base 1303 is not limited to Figure 4A The structure shown in FIG. The lower side of the frame 1301 can also serve as a base. The frame 1301 and the display unit 1302 can be curved, so that the display surface of the display unit 1302 is curved. The radius of curvature can be in the range of 5000 mm to 6000 mm.

[0278] Figure 4B is a schematic diagram of another example of the display device according to this embodiment. Figure 4BDisplay device 1310 is configured to be foldable and is a so-called foldable display device. Display device 1310 includes a first display unit 1311, a second display unit 1312, a housing 1313, and a folding point 1314. First display unit 1311 and second display unit 1312 may include a light-emitting device according to this embodiment. First display unit 1311 and second display unit 1312 may be a single display device without a connection point. First display unit 1311 and second display unit 1312 may be separated by a folding point. First display unit 1311 and second display unit 1312 may display different images or a single image.

[0279] Figure 5A 14 is a schematic diagram of an example of a lighting device according to the present embodiment. Lighting device 1400 may include a housing 1401, a light source 1402, a circuit substrate 1403, an optical filter 1404 that transmits light emitted by light source 1402, and a light diffusion unit 1405. Light source 1402 may include an organic light-emitting element according to the present embodiment. The optical filter may be a filter for improving the color rendering of the light source. The light diffusion unit can effectively diffuse the light from the light source and diffuse the light widely as during illumination. The optical filter and the light diffusion unit may be provided on the light output side of the lighting. A cover may be provided on the outermost side as needed.

[0280] For example, the lighting device is an indoor lighting device. The lighting device can emit white light, daylight white light, or light of any color from blue to red. The lighting device can have a light control circuit for controlling such light or a color control circuit for controlling the color of the emitted light. The lighting device can include an organic light-emitting element according to this embodiment and a power supply circuit connected thereto. The power supply circuit is a circuit that converts AC voltage into DC voltage. The color temperature of white is 4200K, and the color temperature of daylight white is 5000K. The lighting device can have a color filter.

[0281] The lighting device according to the present embodiment may include a heat dissipation unit. The heat dissipation unit releases heat from the device to the outside and may be a metal with high specific heat or liquid silicon.

[0282] Figure 5B 15 is a schematic diagram of a car as an example of a mobile object according to this embodiment. The car has taillights as an example of lamps. The car 1500 may have taillights 1501 that light up when a braking operation is performed, etc.

[0283] Taillight 1501 may include an organic light-emitting element according to this embodiment. Taillight 1501 may include a protective member for protecting the organic light-emitting element. The protective member may be formed of any transparent material having a suitably high strength, such as polycarbonate. Polycarbonate may be mixed with a furandicarboxylic acid derivative or an acrylonitrile derivative.

[0284] Automobile 1500 may include a vehicle body 1503 and a window 1502 on vehicle body 1503. Window 1502 may be a transparent display, as long as it is not a window used to identify the front and rear of the vehicle. The transparent display may include an organic light-emitting element according to this embodiment. In such cases, the constituent materials of the organic light-emitting element, such as electrodes, are transparent materials.

[0285] The mobile object according to this embodiment can be a ship, an aircraft, or an unmanned aerial vehicle. The mobile object can include a body and a lamp disposed on the body. The lamp can emit light to indicate the position of the body. The lamp includes the organic light-emitting element according to this embodiment.

[0286] The following references Figure 6A and Figure 6B Application examples of the display device according to each embodiment will be described. The display device can be applied to a system that can be worn as a wearable device, such as smart glasses, a head-mounted display (HMD), or smart contact lenses. Image-display devices used in such applications include image-display devices that can photoelectrically convert visible light and display devices that can emit visible light.

[0287] Figure 6A 1 shows glasses 1600 (smart glasses) according to an application example. An imaging device 1602, such as a complementary metal oxide semiconductor (CMOS) sensor or a single-photon avalanche photodiode (SPAD), is provided on the front side of a lens 1601 of the glasses 1600. A display device according to an embodiment is provided on the back side of the lens 1601.

[0288] The glasses 1600 further include a controller 1603. The controller 1603 serves as a power source for supplying power to the camera 1602 and the display device according to one embodiment. The controller 1603 controls the operation of the camera 1602 and the display device. The lens 1601 has an optical system for focusing light on the camera 1602.

[0289] Figure 6BGlasses 1610 (smart glasses) according to an application example are shown. Glasses 1610 have a controller 1612, which includes a camera corresponding to the camera 1602, and a display device. Lenses 1611 include an optical system for projecting light from the camera and display device of the controller 1612, and projecting an image on the lenses 1611. The controller 1612 serves as a power source for supplying power to the camera and display device and controls the operation of the camera and display device. The controller may include a line of sight detection unit for detecting the wearer's line of sight. Line of sight can be detected using infrared irradiation. The infrared irradiation unit emits infrared light to the eyeball of the user who is looking at the displayed image. The infrared light reflected from the eyeball is detected by the camera unit including a light receiving element, thereby capturing an image of the eyeball. A reducing unit is provided for reducing light from the infrared irradiation unit to the display unit in a plan view to reduce degradation of image quality.

[0290] The user's line of sight for displaying an image is detected using an eyeball image captured using infrared imaging. Any known technique can be applied to line of sight detection using an eyeball image. For example, a line of sight detection method based on a Purkinje image obtained by reflecting irradiated light off the cornea can be used.

[0291] More specifically, gaze detection processing based on the pupil-corneal reflection method is performed. The user's gaze is detected by calculating a gaze vector representing the direction (rotation angle) of the eyeball based on an image of the pupil and a Purkinje image included in a captured image of the eyeball using the pupil-corneal reflection method.

[0292] A display device according to an embodiment of the present disclosure may include an imaging device including a light receiving element and may control a display image based on visual line information of a user from the imaging device.

[0293] More specifically, based on the line of sight information, the display device determines a first visible area at which the user is looking and a second visible area outside the first visible area. The first visible area and the second visible area can be determined by a controller of the display device or can be received by an external controller. Within the display area of ​​the display device, the first visible area can be controlled to have a higher display resolution than the second visible area. In other words, the second visible area can have a lower resolution than the first visible area.

[0294] The display area includes a first display area and a second display area different from the first display area, and the priority of the first display area and the second display area depends on the line of sight information. The first visible area and the second visible area can be determined by a controller of the display device or can be received by an external controller. The area with a higher priority can be controlled to have a higher resolution than the other area. In other words, the area with a lower priority can have a lower resolution.

[0295] The first visible area or the area with a higher priority can be determined by artificial intelligence (AI). The AI ​​can be a model configured to use an image of the eyeball and the actual direction of the eyeball's gaze in the image as teaching data to estimate the angle of sight and the distance to the target object in front of the sight line from the image of the eyeball. The AI ​​program can be stored in a display device, a camera device, or an external device. The AI ​​program stored in the external device is transmitted to the display device via communication.

[0296] Regarding display control based on visual recognition detection, the present disclosure can be applied to smart glasses that further have a camera for capturing external images. The smart glasses can display the captured external information in real time.

[0297] Figure 7 Schematic diagram of an example of an image forming apparatus according to the present embodiment. Image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photosensitive unit 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a conveying roller 33, and a fixing unit 35. The exposure light source 28 emits light 29 and forms an electrostatic latent image on the surface of the photosensitive unit 27. The exposure light source 28 includes an organic light emitting element according to the present embodiment. The developing unit 31 contains a toner, etc. The charging unit 30 charges the photosensitive unit 27. The transfer unit 32 transfers the developed image to a recording medium 34. The conveying roller 33 conveys the recording medium 34. For example, the recording medium 34 is paper. The fixing unit 35 fixes the image on the recording medium 34.

[0298] Figure 8A and Figure 8B Schematic diagram of the exposure light source 28, wherein a plurality of light emitting units 36 are arranged on a long substrate. Arrow 37 indicates the longitudinal direction of the arrangement of the organic light emitting elements. The longitudinal direction is the same as the direction of the rotation axis of the photosensitive unit 27. This direction can also be referred to as the long axis direction of the photosensitive unit 27. Figure 8A In the embodiment, the light emitting portion 36 is arranged along the long axis direction of the photosensitive unit 27. Figure 8B In, with Figure 8A Differently, the light emitting portions 36 are arranged alternately in the first and second rows along the length direction. The first and second rows are arranged at different positions along the transverse direction. In the first row, the light emitting portions 36 are arranged at intervals. In the second row, the light emitting portions 36 are arranged at positions corresponding to the spaces between the light emitting portions 36 in the first row. Therefore, the light emitting portions 36 are also arranged at intervals along the transverse direction. For example, Figure 8B The arrangement in may also be called a plaid pattern, a houndstooth pattern, or a checkered pattern.

[0299] As described above, a device including the organic light emitting element according to the present embodiment can be used to stably display high-quality images for a long time.

[0300] Example

[0301] The present disclosure is described below using exemplary embodiments, but is not limited to these exemplary embodiments.

[0302] [Exemplary Embodiment 1 (Synthesis of Exemplary Compounds A25 and A35)]

[0303] Exemplary compounds A25 and A35 were synthesized by the following synthetic scheme.

[0304]

[0305] (1) Synthesis of compound m-3

[0306] The following reagents and solvents were added to a 200 ml recovery flask.

[0307] Compound m-1: 4.0 g (16.8 mmol)

[0308] Compound m-2: 3.2 g (18.5 mmol)

[0309] Pd(PPh3)4:0.19g

[0310] Toluene: 20ml

[0311] Ethanol: 10ml

[0312] 2M sodium carbonate aqueous solution: 20ml

[0313] The reaction solution was then heated to reflux under nitrogen flow and stirred for 6 hours. After the reaction was complete, water was added to the product and separatory was performed. The products therefrom was then dissolved in chloroform and purified by column chromatography (chloroform). 3.7 g (yield: 76%) of compound m-3 as a light yellow solid was obtained from chloroform / methanol recrystallization.

[0314] (2) Synthesis of compound m-4

[0315] The following reagents and solvents were added to a 200 ml recovery flask.

[0316] Compound m-3: 3.5 g (12.2 mmol)

[0317] Phosphorus oxychloride: 105ml

[0318] The reaction solution was then heated to 130°C under a nitrogen stream and stirred for 3 days. After the reaction was complete, water was added to the product and the liquids were separated. The resulting product was then dissolved in chloroform and purified by column chromatography (chloroform). Recrystallization from chloroform / methanol gave 2.0 g (yield: 55%) of compound m-4 as a pale yellow solid.

[0319] (3) Synthesis of Compound m-5

[0320] The following reagents and solvents were added to a 200 ml recovery flask.

[0321] Compound m-4: 2.0 g (6.5 mmol)

[0322] Pd(dba)2:0.23g

[0323] P(Cy)3-HBF4:0.29g

[0324] DMAc: 20ml

[0325] Potassium carbonate: 2.7 g (19.6 mmol)

[0326] The reaction solution is then heated to 150 ° C and stirred for 6 hours under a nitrogen stream. After the reaction is complete, water is added to the product and liquid separation is carried out. The resulting product is then dissolved in chloroform and purified by column chromatography (chloroform). From chloroform / methanol recrystallization, 0.49 g (yield: 28%) of compound m-5 as a light yellow solid is obtained.

[0327] (4) Synthesis of Compound m-6

[0328] The following reagents and solvents were added to a 200 ml recovery flask.

[0329] 2-Ethoxyethanol: 12ml

[0330] Iridium(III) chloride hydrate: 0.19g

[0331] Compound m-5: 0.4 g (1.5 mmol)

[0332] The reaction solution was then heated to 120° C. and stirred for 6 hours. After cooling, water was added to the product, and the product was filtered and washed with water. The product was dried to obtain 0.5 g (yield: 90%) of compound m-6 as a yellow solid.

[0333] (5) Synthesis of Exemplary Compound A25

[0334] The following reagents and solvents were added to a 200 ml recovery flask.

[0335] 2-Ethoxyethanol: 30ml

[0336] Compound m-6: 0.5 g (0.3 mmol)

[0337] Compound m-7: 0.13 g (1.3 mmol)

[0338] Sodium carbonate: 0.3 g (3.3 mmol)

[0339] The reaction solution was then heated to 100° C. and stirred for 6 hours. After cooling, methanol was added to the product, and the product was filtered and washed with methanol. The product was dried to obtain 0.3 g (yield: 63%) of exemplary compound A25 as a yellow solid.

[0340] Mass spectrometry analysis of exemplary compound A25 was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[0341] [MALDI-TOF-MS]

[0342] Found: m / z = 828 Calculated: C 45 H 35 IrN2O2=828

[0343] (6) Synthesis of Exemplary Compound A35

[0344] The following reagents and solvents were added to a 50 ml recovery flask.

[0345] Exemplary compound A25: 0.2 g (0.2 mmol)

[0346] Compound m-5: 0.7 g (2.4 mmol)

[0347] Glycerin: 15ml

[0348] The reaction solution was then heated to 230°C and stirred for 3 hours. After cooling to 100°C, 2 mL of toluene was added to the product, which was then cooled to room temperature under stirring. Heptane was then added to the product and filtered. The filter residue was purified by silica gel column chromatography (ethyl acetate) to obtain 0.06 g (yield: 24%) of exemplary compound A35 as a dark yellow solid.

[0349] Mass spectrometry analysis of the exemplary compound A35 was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[0350] [MALDI-TOF-MS]

[0351] Found: m / z = 997 Calculated: C60 H 42 IrN3=997

[0352] [Exemplary Embodiments 2 to 7 (Synthesis of Exemplary Compounds)]

[0353] As shown in Table 4, the exemplary compounds of Exemplary Embodiments 2 to 7 were synthesized in the same manner as in Exemplary Embodiment 1, except that the raw materials m-1, m-2, and m-7 of Exemplary Embodiment 1 were changed. Measured values ​​m / z measured by mass spectrometry analysis in the same manner as in Exemplary Embodiment 1 are also shown.

[0354] Table 4

[0355]

[0356] [Exemplary Embodiment 8 (Synthesis of Exemplary Compounds E29 and E33)] Exemplary compounds E29 and E33 were synthesized by the following synthesis scheme.

[0357]

[0358] (1) Synthesis of compound n-3

[0359] The following reagents and solvents were added to a 200 ml recovery flask.

[0360] Compound n-1: 4.0 g (16.7 mmol)

[0361] Compound n-2: 3.5 g (18.4 mmol)

[0362] Pd(PPh3)4:0.19g

[0363] Toluene: 20ml

[0364] Ethanol: 10ml

[0365] 2M sodium carbonate aqueous solution: 20ml

[0366] The reaction solution was then heated to reflux under nitrogen flow and stirred for 6 hours. After the reaction was complete, water was added to the product and separatory was performed. The resulting product was then dissolved in chloroform and purified by column chromatography (chloroform). 3.3 g (yield: 64%) of compound n-3 as a light yellow solid was obtained from chloroform / methanol recrystallization.

[0367] (3) Synthesis of Compound m-4

[0368] The following reagents and solvents were added to a 200 ml recovery flask.

[0369] Compound n-3: 3.0 g (9.8 mmol)

[0370] P(dba)2:0.34g

[0371] P(Cy)3-HBF4:0.43g

[0372] DMAc: 30ml

[0373] Potassium carbonate: 4.1 g (29.4 mmol)

[0374] The reaction solution was then heated to 150° C. under a nitrogen stream and stirred for 6 hours. After the reaction was complete, water was added to the product and separation was performed. The resulting product was then dissolved in chloroform and purified by column chromatography (chloroform). 0.8 g (yield: 29%) of compound n-4 as a pale yellow solid was obtained from chloroform / methanol recrystallization.

[0375] (4) Synthesis of Compound n-5

[0376] The following reagents and solvents were added to a 200 ml recovery flask.

[0377] 2-Ethoxyethanol: 24ml

[0378] Iridium (III) chloride hydrate: 0.32g

[0379] Compound n-4: 0.7 g (2.6 mmol)

[0380] The reaction solution was then heated to 120° C. and stirred for 6 hours. After cooling, water was added to the product, and the product was filtered and washed with water. The product was dried to obtain 0.9 g (yield: 89%) of compound n-5 as a yellow solid.

[0381] (5) Synthesis of Exemplary Compound E29

[0382] The following reagents and solvents were added to a 200 ml recovery flask.

[0383] 2-Ethoxyethanol: 30ml

[0384] Compound n-5: 0.8 g (0.6 mmol)

[0385] Compound n-6: 0.2 g (2.5 mmol)

[0386] Sodium carbonate: 0.6 g (6.3 mmol)

[0387] The reaction solution was then heated to 100° C. and stirred for 6 hours. After cooling, methanol was added to the product, and the product was filtered and washed with methanol. The product was dried to obtain 0.5 g (yield: 61%) of exemplary compound E29 as a yellow solid.

[0388] Mass spectrometry analysis of the exemplary compound E29 was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[0389] [MALDI-TOF-MS]

[0390] Found: m / z = 828 Calculated: C 45 H 35 IrN2O2=828

[0391] (6) Synthesis of Exemplary Compound E33

[0392] The following reagents and solvents were added to a 50 ml recovery flask.

[0393] Exemplary compound E29: 0.5 g (0.5 mmol)

[0394] Compound n-4: 1.6 g (6.0 mmol)

[0395] Glycerin: 15ml

[0396] The reaction solution was then heated to 230°C and stirred for 3 hours. After cooling to 100°C, 2 mL of toluene was added to the product, which was then cooled to room temperature under stirring. Heptane was then added to the product and filtered. The filter residue was purified by silica gel column chromatography (ethyl acetate) to give 0.1 g (yield: 22%) of dark yellow solid E33.

[0397] Mass spectrometry analysis of exemplary compound E33 was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[0398] [MALDI-TOF-MS]

[0399] Found: m / z = 997 Calculated: C 60 H 42 IrN3=997

[0400] [Exemplary Embodiments 9 to 16 (Synthesis of Exemplary Compounds)]

[0401] As shown in Table 5, the exemplary compounds of Exemplary Embodiments 9 to 16 were synthesized in the same manner as in Exemplary Embodiment 8, except that the raw materials n-1, n-2, and n-6 ​​of Exemplary Embodiment 8 were changed. Measured values ​​m / z measured by mass spectrometry analysis in the same manner as in Exemplary Embodiment 8 are also shown.

[0402] Table 5

[0403]

[0404] [Exemplary Embodiments 17 to 25 (Synthesis of Exemplary Compounds)]

[0405] As shown in Table 6, the exemplary compounds of Exemplary Embodiments 17 to 21 were synthesized in the same manner as in Exemplary Embodiment 1, except that the starting materials m-1, m-2, and m-5 were changed in Exemplary Embodiment 1. As shown in Table 6, the exemplary compounds of Exemplary Embodiments 22 to 25 were synthesized in the same manner as in Exemplary Embodiment 8, except that the starting materials n-1, n-2, and n-4 were changed in Exemplary Embodiment 8. Measured values ​​m / z measured by mass spectrometry in the same manner as in Exemplary Embodiments 1 and 8 are also shown.

[0406] Table 6

[0407]

[0408] [Exemplary Embodiment 26 (Synthesis of Exemplary Compound A1)]

[0409] Exemplary Compound A1 was synthesized by the following synthetic scheme.

[0410]

[0411] The synthesis of compound k-2 is the same as that of compound m-6 (4) of Exemplary Embodiment 1 and will not be described here.

[0412] (2) Synthesis of Exemplary Compound A1

[0413] The following reagents and solvents were added to a 200 ml recovery flask.

[0414] Compound k-2: 1.0 g (0.9 mmol)

[0415] AgOTf: 0.5 g (1.9 mmol)

[0416] Dichloromethane: 50ml

[0417] Methanol: 2ml

[0418] The reaction solution was then stirred at room temperature for 6 hours.The solvent was then distilled off under reduced pressure, and a yellow solid was formed.

[0419] A 200 ml recovery flask was charged with the yellow solid and the following reagents and solvents.

[0420] Ethanol: 30ml

[0421] Compound k-3: 0.4 g (1.9 mmol)

[0422] The reaction solution was then heated to 85° C. and stirred for 3 hours. After cooling, it was filtered. The filter residue was purified by silica gel column chromatography (chloroform:heptane=1:1) to obtain 0.7 g (yield: 52%) of dark yellow solid A1.

[0423] Mass spectrometry analysis of the exemplary compound A1 was performed using MALDI-TOF-MS (Autoflex LRF manufactured by Bruker).

[0424] [MALDI-TOF-MS]

[0425] Found: m / z = 769 Calculated: C 42 H 30 IrN3=769

[0426] [Exemplary Embodiments 27 to 43 (Synthesis of Exemplary Compounds)]

[0427] As shown in Tables 7 and 8, the exemplary compounds of Exemplary Embodiments 27 to 43 were synthesized in the same manner as in Exemplary Embodiment 26, except that the starting materials k-1 and k-3 of Exemplary Embodiment 26 were changed. Measured values ​​m / z measured by mass spectrometry analysis in the same manner as in Exemplary Embodiment 26 are also shown.

[0428] Table 7

[0429]

[0430] Table 8

[0431]

[0432] [Exemplary embodiment 44]

[0433] A bottom-emitting organic light-emitting element is produced, which includes an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially formed on a substrate.

[0434] First, an ITO film was formed on a glass substrate and patterned as desired to form an ITO electrode (anode). The thickness of the ITO electrode was 100 nm. The substrate on which the ITO electrode was formed was used as an ITO substrate in the following process. -4 Vacuum deposition was performed by resistance heating in a vacuum chamber of 1000 Pa to continuously form the organic compound layer and electrode layer shown in Table 9 on the ITO substrate. The electrode area of ​​the counter electrode (metal electrode layer, cathode) was 3 mm 2 .

[0435] Table 9

[0436]

[0437] The characteristics of the element were measured and evaluated. The maximum emission wavelength of the light-emitting element was 522 nm and the maximum external quantum efficiency (EQE) was 12%. At 100 mA / cm 2 A continuous operation test was conducted at a current density of 1.5 to measure the time (LT95) when the luminance degradation rate reaches 5%. Assuming that the time (LT95) when the luminance degradation rate reaches 5% of Comparative Example 1 is 1.0, the LT95 (relative value) of this exemplary embodiment is 1.4.

[0438] In the present exemplary embodiment, regarding the measuring device, more specifically, the current-voltage characteristics were measured with a microammeter 4140B manufactured by Hewlett-Packard Co., and the light emission luminance was measured with a BM7 manufactured by Topcon Corporation.

[0439] [Exemplary Embodiments 45 to 68, Comparative Examples 1 and 2]

[0440] An organic light-emitting element was produced in the same manner as in Exemplary Embodiment 44, except that the materials for forming each layer were appropriately changed to the compounds shown in Table 10. The layers not shown in Table 10 had the same structures as in Exemplary Embodiment 44. The characteristics of the element were measured and evaluated in the same manner as in Exemplary Embodiment 44. Table 10 shows the measurement results together with the results of Exemplary Embodiment 44.

[0441] Table 10

[0442]

[0443] Table 10 shows that the maximum external quantum efficiency (EQE) of Comparative Examples 1 and 2 is in the range of 8% to 9%, and the maximum external quantum efficiency of exemplary embodiments 44 to 68 is in the range of 10% to 15%. Therefore, the organic light-emitting elements of exemplary embodiments 44 to 68 have higher luminous efficiency. This may be because the organic compounds contained as guests in the organic light-emitting elements of exemplary embodiments 44 to 68 have higher quantum yields than the organic compounds (comparative compound 1) contained as guests in the organic light-emitting elements of comparative examples 1 and 2. Comparative compound 1 is a compound in which the auxiliary ligand of compound 1-b described in PTL 1 is changed from acetylacetone to phenylpyridine. The organic compounds contained as guests in the organic light-emitting elements of exemplary embodiments 44 to 68 have a ring structure containing bridging carbon atoms constituting a dibenzo[f,h]quinoline skeleton. This results in a high radiative decay rate due to good CT properties and transition dipole moment, and a low non-radiative decay rate due to high rigidity. This results in a high quantum yield of each organic compound. Therefore, it is considered that the organic light emitting elements of Exemplary Embodiments 44 to 68 exhibit high light emitting efficiency.

[0444] Table 10 shows that the exemplary embodiments (Exemplary Embodiments 45, 51 to 53, 58, 60, 64, and 65) containing an organic compound having a partial structure IrL represented by the general formula [C-1] or [C-2] as a guest in the light-emitting layer have higher maximum external quantum efficiencies. This is probably because the carbon atom adjacent to the carbon atom σ-bonded to the Ir metal in the aromatic ring σ-bonded to the Ir metal has a methyl group, which improves the balance between the MLCT property and the π-π* characteristics of the ligand.

[0445] Table 10 also shows that exemplary embodiments 44 to 68 have longer LT95 and longer life (higher durability) than the organic light-emitting elements of Comparative Examples 1 and 2. This is probably because each organic compound contained in the organic light-emitting elements of exemplary embodiments 44 to 68 as a guest in the light-emitting layer has a ring structure containing a bridging carbon atom constituting a dibenzo[f,h]quinoline skeleton, resulting in a ligand with lower symmetry and high sublimability. Therefore, it is believed that each organic compound has high stability during sublimation purification or vapor deposition, and a high-purity evaporated film can be produced. Therefore, the organic light-emitting element has a long life.

[0446] [Exemplary embodiment 69]

[0447] An organic light emitting element was produced in the same manner as in Exemplary Embodiment 44, except that the organic compound layer and the electrode layer shown in Table 11 were successively formed.

[0448] Table 11

[0449]

[0450] The characteristics of the element were measured and evaluated. The light-emitting element had green emission color and a maximum external quantum efficiency (EQE) of 19%.

[0451] [Exemplary Embodiments 70 to 100]

[0452] An organic light-emitting element was produced in the same manner as in Exemplary Embodiment 69, except that the materials used to form each layer were appropriately changed to the compounds shown in Table 12. The layers not shown in Table 12 had the same structures as in Exemplary Embodiment 69. The characteristics of the element were measured and evaluated in the same manner as in Exemplary Embodiment 69. Table 12 shows the measurement results together with the results of Exemplary Embodiment 69.

[0453] Table 12

[0454]

[0455] As described above, use of the organic compound represented by the general formula [1] as a guest in a light-emitting layer can provide an organic light-emitting element having high maximum external quantum efficiency and light-emitting efficiency.

[0456] The present disclosure can provide an organic compound having good light-emitting properties.

[0457] While the present disclosure has been described with reference to exemplary embodiments, it is to be understood that the present disclosure is not limited to the exemplary embodiments. The scope of the following claims is to be accorded the broadest interpretation so as to encompass all such modifications and equivalent structures and functions.

Claims

1. An organic compound represented by the following general formula [1]: Ir L m L' n [1] It is characterized in that Ir represents iridium, L and L' represent different bidentate ligands, m represents an integer in the range of 1 to 3, when m is 1, n is 2, when m is 2, n is 1, and when m is 3, n is 0, the partial structure IrL represents a partial structure represented by the following general formula [A-1] or [A-2], and the partial structure IrL' represents a partial structure represented by the following general formula [B-1] or [B-2], when m is 2 or more, a plurality of L's are the same or different, and when n is 2, a plurality of L's are the same or different, Y1 to Y in the general formulas [A-1], [A-2] and [B-2] 24 is a carbon atom having a hydrogen atom, a deuterium atom or a substituent R, and when Y1 to Y 24 When two or more of represent carbon atoms having the substituent R, the substituent R has the same or different structures, The substituent R represents a substituent independently selected from a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a substituted or unsubstituted aromatic hydrocarbon group, wherein the aromatic hydrocarbon group is a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group or a fluorenyl group, When Y1 to Y 24 When any two adjacent ones of the carbon atoms simultaneously represent carbon atoms and have the substituent R, the substituent R can be combined together to form a ring, and the ring structure is a benzene ring or a naphthalene ring, Z1 and Z2 in the general formulas [A-1] and [A-2] are independently selected from oxygen atoms, sulfur atoms, SiR1R2, CR1R2, and CR1=CR2, and when Z1 and Z2 are independently CR1=CR2, R1 and R2 may be combined together to form a benzene ring or a naphthalene ring, and R1 and R2 in the general formulas [A-1], [A-2] and [B-1] are independently selected from fluorine atoms, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and substituted or unsubstituted aromatic hydrocarbon groups, and R3 to R5 are independently selected from fluorine atoms, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and substituted or unsubstituted aromatic hydrocarbon groups, wherein the aromatic hydrocarbon group is phenyl, naphthyl, indenyl, biphenyl, terphenyl or fluorenyl, and When the alkyl group, silyl group and aromatic hydrocarbon group have a substitution, the substitution is a fluoro group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a phenyl group or a biphenyl group.

2. The organic compound according to claim 1, wherein the general formula [A-1] is independently selected from the following general formulas [A-11] to [A-14], and the general formula [A-2] is independently selected from the following general formulas [A-21] to [A-24], X1 to X2 in the general formulas [A-11] to [A-14] and [A-21] to [A-24] 68 is a carbon atom having a hydrogen atom, a deuterium atom or a substituent R, and when X1 to X 68 When two or more of represent carbon atoms having the substituent R, the substituent R has the same or different structures, The substituent R represents a substituent independently selected from a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted silyl group, and a substituted or unsubstituted aromatic hydrocarbon group, wherein the aromatic hydrocarbon group is a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group or a fluorenyl group, When X1 to X2 in the general formulas [A-11] to [A-14] and [A-21] to [A-24] 68 When any two adjacent ones of the carbon atoms simultaneously represent carbon atoms and have the substituent R, the substituent R can be combined together to form a ring, and the ring structure is a benzene ring or a naphthalene ring, and R6 to R9 in the general formulas [A-11] and [A-21] are independently selected from a fluorine atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group, wherein the aromatic hydrocarbon group is a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group or a fluorenyl group, and When the alkyl group, silyl group and aromatic hydrocarbon group have a substitution, the substitution is a fluoro group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a phenyl group or a biphenyl group. 3 . The organic compound according to claim 2 , wherein the partial structure IrL in the general formula [1] is represented by the general formula [A-11]. 4 . The organic compound according to claim 2 , wherein the partial structure IrL in the general formula [1] is represented by the general formula [A-12]. 5 . The organic compound according to claim 2 , wherein the partial structure IrL in the general formula [1] is represented by the general formula [A-13]. 6 . The organic compound according to claim 2 , wherein the partial structure IrL in the general formula [1] is represented by the general formula [A-14].

7. The organic compound according to claim 2, wherein the partial structure IrL in the general formula [1] is represented by the general formula [A-21].

8. The organic compound according to claim 2, wherein the partial structure IrL in the general formula [1] is represented by the general formula [A-22].

9. The organic compound according to claim 2, wherein the partial structure IrL in the general formula [1] is represented by the general formula [A-23].

10. The organic compound according to claim 2, wherein the partial structure IrL in the general formula [1] is represented by the general formula [A-24].

11. An organic light-emitting element, comprising: a first electrode; a second electrode; and The organic compound layer located between the first electrode and the second electrode and having at least a light-emitting layer is characterized in that: the organic compound layer contains the organic compound according to claim 1, wherein the light-emitting layer comprises the organic compound, wherein the light-emitting layer comprises a first compound different from the organic compound, wherein the first compound has a carbazole structure, or the first compound has a structure selected from triphenylene structure, phenanthrene structure, The first compound has at least one structure selected from a dibenzothiophene structure and a dibenzofuran structure, or the first compound has at least one structure selected from a dibenzothiophene structure and a dibenzofuran structure. 12 . The organic light emitting element according to claim 11 , wherein the amount of the organic compound in the light emitting layer ranges from 1% by mass to 30% by mass. 13 . The organic light-emitting element according to claim 11 , wherein when the first compound has a carbazole structure, the first compound further has an azine ring. The organic light-emitting element according to claim 11 , wherein the first compound does not have sp 3 carbon.

15. The organic light-emitting element according to claim 11, wherein the light-emitting layer further comprises a second compound different from the organic compound and the first compound, the second compound having an azine ring, or the second compound having at least one structure selected from a xanthone structure, a thioxanthone structure, and a benzophenone structure.

16. The organic light emitting element according to claim 11, wherein the light emitting layer is a first light emitting layer, The organic light emitting element further includes a second light emitting layer that is different from the first light emitting layer and is disposed between the first light emitting layer and the first electrode or between the first light emitting layer and the second electrode, and The second light-emitting layer emits light of a different color from light emitted by the first light-emitting layer. The organic light-emitting element according to claim 16 , wherein the organic light-emitting element emits white light.

18. A display device comprising: Multiple pixels, It is characterized in that at least one of the plurality of pixels includes an organic light emitting element according to any one of claims 11 to 17 and an active element connected to the organic light emitting element. The display apparatus according to claim 18 , further comprising a color filter.

20. A photoelectric conversion device comprising: an optical unit having a plurality of lenses; an imaging element configured to receive light passing through the optical unit; and a display unit configured to display an image captured by the imaging element, It is characterized in that the display unit includes the organic light emitting element according to any one of claims 11 to 17.

21. An electronic device comprising: case; a communication unit configured to communicate with the outside; and Display unit, It is characterized in that the display unit includes the organic light emitting element according to any one of claims 11 to 17.

22. A lighting device comprising: light source; and light diffusion unit or optical filter, It is characterized in that the light source comprises the organic light emitting element according to any one of claims 11 to 17.

23. A mobile object comprising: body; and A lamp is provided on the body, It is characterized in that the lamp comprises the organic light emitting element according to any one of claims 11 to 17.

24. An exposure light source for an electrophotographic image forming apparatus, characterized in that: The exposure light source includes the organic light emitting element according to any one of claims 11 to 17.

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