Organic compound and organic light-emitting element

Abstract

The organic compound is characterized by being represented by formula (1). In formula (1), rings A to C are independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 50 carbon atoms and substituted or unsubstituted heterocyclic groups having 3 to 50 carbon atoms. EWG is an electron withdrawing group, an aryl group having at least one electron withdrawing group, or a heterocyclic group having at least one electron withdrawing group. n is an integer of 1 or more.

Description

Organic compound and organic light-emitting device

[0001] The present invention relates to an organic compound and an organic light-emitting device using the same.

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

[0003] Incidentally, there has been active research into compounds suitable for organic light-emitting devices. Patent Document 1 describes compound Ref-1 as a compound having an indolocarbazole skeleton.

[0004]

[0005] International Publication No. 2019 / 111971

[0006] However, the compounds specifically described in Patent Document 1 are compounds in which, when the central benzene in the indolocarbazole skeleton has a substituent, the substituent is an aryl group or an aryl group having an alkyl group, and therefore the oxidation stability of the compounds leaves room for improvement.

[0007] The present invention has been made in view of the above problems, and an object of the present invention is to provide an organic compound having excellent oxidation stability.

[0008] The organic compound according to the present invention is characterized by being represented by formula (1).

[0009]

[0010] In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having from 6 to 50 carbon atoms and substituted or unsubstituted heterocyclic groups having from 3 to 50 carbon atoms. When rings A to C have a substituent, the substituent is a deuterium atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heteroaryloxy group, a silyl group, an amino group, or a cyano group.

[0011] EWG is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one or more electron-withdrawing groups.

[0012] n is an integer of 1 or more.

[0013] According to the present invention, an organic compound having excellent oxidation stability can be provided.

[0014] FIG. 1 is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention. FIG. 2 is a schematic cross-sectional view showing an example of a display device using an organic EL element according to one embodiment of the present invention. FIG. 3 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 4 is a schematic view showing an example of an imaging device according to one embodiment of the present invention. FIG. 5 is a schematic view showing an example of an electronic device according to one embodiment of the present invention. FIG. 6 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 7 is a schematic view showing an example of a bendable display device. FIG. 8 is a schematic view showing an example of a lighting device according to one embodiment of the present invention. FIG. 9 is a schematic view showing an example of an automobile having a vehicle lamp according to one embodiment of the present invention. FIG. 10 is a schematic view showing an example of a wearable device according to one embodiment of the present invention. FIG. 11 is a schematic view showing an example of a wearable device according to one embodiment of the present invention, having an imaging device. FIG. 12 is a schematic view showing an example of an image forming apparatus according to one embodiment of the present invention. FIG. 13 is a schematic view showing an example of an exposure light source of an image forming apparatus according to one embodiment of the present invention. FIG. 14 is a schematic view showing an example of an exposure light source of an image forming apparatus according to one embodiment of the present invention.

[0015] In this specification, examples of halogen atoms include, but are not limited to, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0016] The alkyl group may have from 1 to 20 carbon atoms, from 1 to 10 carbon atoms, or from 1 to 4 carbon atoms. Specific examples include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a tertiary pentyl group, a 3-methylpentan-3-yl group, a 1-adamantyl group, and a 2-adamantyl group, but are not limited to these.

[0017] The aryl group may have from 6 to 50 carbon atoms, from 6 to 20 carbon atoms, from 6 to 14 carbon atoms, or from 6 to 12 carbon atoms. Specific examples include, but are not limited to, a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, an anthranyl group, a perylenyl group, a chrysenyl group, and a fluoranthenyl group.

[0018] The heterocyclic group may have from 3 to 50 carbon atoms, from 3 to 20 carbon atoms, from 3 to 17 carbon atoms, or from 3 to 12 carbon atoms. Specific examples include, but are not limited to, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a carbazolyl group, an acridinyl group, and a phenanthrolyl group.

[0019] The amino group may be a substituted amino group substituted with an alkyl group or an aryl group, and may be a substituted amino group substituted with an alkyl group having from 1 to 4 carbon atoms or an aryl group having from 6 to 12 carbon atoms. Specific examples include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisolylamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, and an N-piperidyl group.

[0020] The alkoxy group may have from 1 to 10 carbon atoms, or from 1 to 4 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, and a benzyloxy group.

[0021] Specific examples of the aryloxy group include, but are not limited to, a phenoxy group.

[0022] Specific examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0023] Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0024] Examples of substituents that the alkyl group, alkoxy group, amino group, aryloxy group, silyl group, aryl group, and heterocyclic group may further have include, but are not limited to, halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, and tertiary butyl group; alkoxy groups such as methoxy group, ethoxy group, and propoxy group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group; aryloxy groups such as phenoxy group; aryl groups such as phenyl group and biphenyl group; heterocyclic groups such as pyridyl group and pyrrolyl group; and cyano group.

[0025] (1) Organic Compound First, the organic compound according to the present invention will be described.

[0026] The organic compound according to the present invention is an organic compound represented by formula (1).

[0027]

[0028] In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having from 6 to 50 carbon atoms and substituted or unsubstituted heterocyclic groups having from 3 to 50 carbon atoms.

[0029] When ring A to ring C have a substituent, the substituent is a deuterium atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heteroaryloxy group, a silyl group, an amino group, or a cyano group.

[0030] When rings A to C have a substituent, the substituent may be an alkyl group, an aryl group, an amino group, or a heterocyclic group, and is preferably an alkyl group, an aryl group, or a heterocyclic group. Specifically, the substituent may be an alkyl group having from 1 to 4 carbon atoms, an aryl group having from 6 to 14 carbon atoms, or a heterocyclic group having from 3 to 12 carbon atoms. More specifically, the substituent may be a methyl group, an isopropyl group, a tert-butyl group, a phenyl group, a phenyl group having a tert-butyl group, a phenyl group having a methyl group, or a dibenzofuranyl group. Furthermore, the amino group may be a diphenylamino group, and the phenyl group in the diphenylamino group may have an alkyl group having from 1 to 4 carbon atoms. Specifically, the alkyl group may be an isopropyl group or a tert-butyl group.

[0031] Rings A to C may be a substituted or unsubstituted aryl group having from 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having from 3 to 17 carbon atoms.

[0032] Specifically, ring A may be a benzene skeleton, a naphthalene skeleton, or a fluorene skeleton, or may be a benzene skeleton or a naphthalene skeleton. Ring B may be a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton, or may be a benzene skeleton or a benzofuran skeleton. Ring C may be a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton, or may be a benzene skeleton or a benzofuran skeleton.

[0033] EWG is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group. EWG may be an aryl group having from 6 to 20 carbon atoms and having at least one electron-withdrawing group, or a heterocyclic group having from 3 to 17 carbon atoms and having at least one electron-withdrawing group.

[0034] Here, the electron-withdrawing group is a trifluoromethyl group, a trichloromethyl group, a nitro group, a cyano group, an aldehyde group, a ketone group, an ester group, a carboxylic acid group, a sulfonyl group, a sulfonic acid group, a pyridyl group, a triazinyl group, a halogen atom, etc. Among these, the electron-withdrawing group preferably has a Hammett's substituent constant of 0.01 or more and 0.70 or less, and more specifically, a trifluoromethyl group, a cyano group, or a fluorine atom is preferred.

[0035] On the other hand, a bipyridyl group is defined as a structure in which a heterocyclic pyridyl group has an electron-withdrawing pyridyl group, and a benzonitrile group is defined as a structure in which an aryl phenyl group has an electron-withdrawing cyano group.

[0036] n is an integer of 1 or more. The possible values ​​of n are defined by the structure of ring A. For example, when ring A is a benzene skeleton, n is 1 or 2, and when ring B is a naphthalene skeleton, n is an integer of 1 or more and 4 or less.

[0037] Formula (1) may have a structure represented by the following formula (2) or formula (3). Formula (2) is a compound in which ring A in formula (1) is a benzene skeleton. Formula (3) is a compound in which ring A in formula (1) is a naphthalene skeleton.

[0038]

[0039] In formula (2), R １ ~R １６ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ５ and R ６ , R６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １２ and R １３ , R １３ and R １４ may be bonded to each other to form a ring. ３ and R ４ , and R １０ and R １１ are preferably bonded to each other to form a ring. ５ and R ６ , and R １２ and R １３ are preferably bonded to each other to form a ring. The ring may be a substituted or unsubstituted aryl group having 6 to 12 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms. Specifically, it may be a substituted or unsubstituted benzofuran skeleton or a substituted or unsubstituted benzothiophene skeleton. However, R １５ and R １６ At least one of the groups is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

[0040] In formula (2), when the organic compound according to the present invention has a substituent, R ３ , R ４ , R ５ , R ６ , R １０ , R １１ , R １２ , R １３ may have a substituent, and R ３ , R ６ , R １０ , and R １３ , or R ３ and R １０ , or R ４ and R １１ , or R ５ and R １２ Either pair may have a substituent.

[0041] In formula (3), R ２１ ~R ３８ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２６ and R ２７ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and R ３１ , R ３２ and R ３３ , R ３３ and R ３４ may be bonded to each other to form a ring. ２３ and R ２４ , and R ３０ and R ３１ are preferably bonded to each other to form a ring. ２５ and R ２６ , and R ３２ and R ３３ are preferably bonded to each other to form a ring. The ring may be a substituted or unsubstituted aryl group having 6 to 12 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms. Specifically, it may be a substituted or unsubstituted benzofuran skeleton or a substituted or unsubstituted benzothiophene skeleton. However, R ３５ ~R ３８ At least one of the groups is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

[0042] In formula (3), when the organic compound according to the present invention has a substituent, R ２３ , R ２４ , R ２５ , R ２６ , R ３０ , R ３１ , R ３２ , R ３３ may have a substituent, and R ２３ , R ２６ , R ３０ , and R ３３ , or R ２３ and R ３０ , or R ２４ and R ３１ , or R ２５ and R ３２ Either pair may have a substituent.

[0043] Next, the characteristics of the organic compound according to the present invention will be described.

[0044] In the organic compound according to the present invention, the ring A in formula (1) has an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group, so that the HOMO (Highest Occupied Molecular Orbital) is low (far from the vacuum level), and as a result, the organic compound according to the present invention has excellent oxidation stability.

[0045] Here, the HOMO values ​​of compounds A-1 and A-2, which are examples of organic compounds according to the present invention, and compound Ref-1, which is a comparative compound, were determined using Gaussian 16 (Gaussian 16, Revision C.01, M.J. Frisch, et al., Gaussian, Inc. Wallingford, CT, 2019), a molecular orbital calculation software manufactured by Gaussian, Inc. The keyword used was B3LYP / 6-31G*. The results are shown in Table 1.

[0046]

[0047] As can be seen from Table 1, the HOMOs of compounds A-1 and A-2, which are examples of organic compounds according to the present invention, are -5.25 eV and -5.29 eV, respectively, whereas the HOMO of compound Ref-1, a comparative compound, is -5.11 eV. This is thought to be because the organic compounds according to the present invention have electron-withdrawing groups. Therefore, compared to the HOMO of compound Ref-1, the organic compounds according to the present invention are organic compounds with excellent oxidation stability.

[0048] Furthermore, the organic compound according to the present invention can achieve the effects of the present invention by having at least one of an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group. Using the calculation method described above, the HOMO values ​​of compounds A-2, A-3, and A-4, which are examples of organic compounds according to the present invention, and compounds Ref-2 and Ref-3, which are comparative compounds to A-5, were determined. The results are shown in Table 2.

[0049]

[0050] As can be seen from Table 2, the organic compounds according to the present invention exhibited lower HOMO values ​​than the comparative compounds Ref-2 and Ref-3. Therefore, the organic compounds according to the present invention can achieve the effects of the present invention by having at least one of an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group.

[0051] Furthermore, the organic compound according to the present invention is expected to exhibit a smaller half-width value of the emission spectrum, since ring A in formula (1) has an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group.

[0052] Patent Document 1 describes the following compounds Ref-4 and Ref-5, which are compounds in which ring B in formula (1) has an aryl group having an electron-withdrawing group.

[0053]

[0054] The organic compound according to the present invention differs from compounds Ref-4 and Ref-5 in that ring A in formula (1) has an electron-withdrawing group, an aryl group having an electron-withdrawing group, or a heterocyclic group having an electron-withdrawing group. Therefore, the organic compound according to the present invention is expected to have superior color purity compared to compounds Ref-4 and Ref-5.

[0055] The HOMO orbital distributions and LUMO orbital distributions of compounds A-1 and A-2, which are examples of organic compounds according to the present invention, and compounds Ref-4 and Ref-5, which are comparative compounds, were depicted using Gaussian 16 (Gaussian 16, Revision C.01, M.J. Frisch, et al., Gaussian, Inc., Wallingford, CT, 2019), a molecular orbital calculation software manufactured by Gaussian, Inc., USA. The isoelectron density surface (Isosurface Value) was set to 0.02. The results are shown in FIG. 8.

[0056] 8, the HOMO orbital distributions and LUMO orbital distributions of compounds A-1 and A-2, which are examples of organic compounds according to the present invention, are distributed at the center of the structure represented by formula (1). On the other hand, there is a difference between the HOMO orbital distributions and LUMO orbital distributions of compounds Ref-4 and Ref-5, which are comparative compounds (shown by black dotted circles in FIG. 8). In other words, compared to the organic compounds according to the present invention, there is less overlap between the HOMO orbital distributions and LUMO orbital distributions of compounds Ref-4 and Ref-5, which are comparative compounds.

[0057] Generally, when the overlap between the HOMO orbital distribution and the LUMO orbital distribution is small, the structural relaxation between the excited state and the ground state increases, and the emission spectrum tends to be broad. On the other hand, when the overlap between the HOMO orbital distribution and the LUMO orbital distribution is large, the structural relaxation between the excited state and the ground state can be suppressed, and the emission spectrum tends to be sharp.

[0058] Therefore, the organic compound according to the present invention is expected to have a sharper emission spectrum than the comparative compounds Ref-4 and Ref-5. In other words, the organic compound according to the present invention is expected to exhibit superior color purity.

[0059] More preferred embodiments of the organic compound according to the present invention will be described below.

[0060] Among the organic compounds according to the present invention, it is preferable that in formula (1), EWG is an aryl group having at least one electron-withdrawing group. The oscillator strengths of compounds A-1, A-4, and A-6, which are examples of organic compounds according to this embodiment, were determined using Gaussian 16 (Gaussian 16, Revision C.01, M.J. Frisch, et al., Gaussian, Inc., Wallingford, CT, 2019), a molecular orbital calculation software manufactured by Gaussian, Inc., USA. B3LYP / 6-31G* was used as the keyword. The results are shown in Table 3.

[0061]

[0062] From Table 3, it can be seen that the oscillator strength of Compound A-1 is greater than that of Compound A-4 and Compound A-6.

[0063] Here, the relationship between oscillator strength and quantum yield (luminescence efficiency) will be described. As described in paragraph

[0262] of JP 2020-47930 A and paragraph

[0035] of JP 2022-46999 A, compounds with high oscillator strength are known to exhibit high quantum yield (luminescence efficiency).

[0064] Therefore, among the organic compounds according to the present invention, it is preferable that EWG in formula (1) is an aryl group having at least one electron-withdrawing group from the viewpoint of quantum yield (luminous efficiency).

[0065] Furthermore, among the organic compounds according to the present invention, when EWG in formula (1) is an aryl group having at least one electron-withdrawing group, the aryl group preferably has a benzene skeleton. This is because the oscillator strength exhibits a higher value compared to when the aryl group having at least one electron-withdrawing group has a naphthalene skeleton. Using the same calculation method as in Table 3, the oscillator strengths of compounds A-1 and A-7, which are examples of organic compounds according to this embodiment, were determined. The results are shown in Table 4.

[0066]

[0067] Table 4 shows that Compound A-1 exhibits a higher oscillator strength than Compound A-7. As described above, it is known that a high oscillator strength also leads to a high quantum yield (luminescence efficiency). Therefore, from the viewpoint of quantum yield (luminescence efficiency), it is preferable that the aryl group having at least one electron-withdrawing group has a benzene skeleton.

[0068] Furthermore, among the organic compounds according to the present invention, when EWG in formula (1) is an aryl group having at least one electron-withdrawing group and the aryl group is a benzene skeleton, the electron-withdrawing group is preferably bonded to the meta or para position relative to ring A. This is because, in this case, the organic compounds according to this embodiment exhibit higher oscillator strengths. Using the same calculation method as in Table 3, the oscillator strengths of compounds A-1, A-2, and A-8, which are examples of organic compounds according to this embodiment, were determined. The results are shown in Table 5.

[0069]

[0070] Table 5 shows that Compound A-1 and Compound A-2 exhibit higher oscillator strengths than Compound A-8. As described above, it is known that a high oscillator strength also leads to a high quantum yield (luminous efficiency). Therefore, from the viewpoint of quantum yield (luminous efficiency), when EWG in Formula (1) is an aryl group having at least one electron-withdrawing group and the aryl group is a benzene skeleton, the electron-withdrawing group is preferably bonded to the meta or para position relative to Ring A.

[0071] Furthermore, among the organic compounds according to the present invention, the electron-withdrawing group is preferably a trifluoromethyl group, a cyano group, or a fluorine atom. This is because these electron-withdrawing groups have an appropriately strong electron-withdrawing property, resulting in a greater overlap between the HOMO orbital distribution and the LUMO orbital distribution. As a result, the organic compound according to this embodiment is expected to have a smaller half-width. In other words, the organic compound according to this embodiment is expected to have superior color purity.

[0072] Specific examples of the organic compound according to the present invention are shown below, but the present invention is not limited to these.

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] (2) Organic Light-Emitting Device Next, an organic light-emitting device according to one embodiment of the present invention will be described. An organic light-emitting device according to one embodiment of the present invention has a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode, and the other is a cathode. In the organic light-emitting device according to this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has an emitting layer. The organic compound according to the present invention may be contained in the organic compound layer, and preferably contained in the emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the emitting layer may be a single layer or a laminate consisting of multiple layers. When the emitting layer is a multi-layer structure, a charge generation layer may be present between the emitting layers. The charge generation layer may be composed of a compound having a LUMO (Lowest Unoccupied Molecular Orbital) energy level lower than the LUMO energy level of the hole transport layer, and the LUMO energy level of the charge generation layer may be lower than the HOMO energy level of the hole transport layer. Here, the HOMO energy level and the LUMO energy level of the organic compound layer may be the HOMO energy level and the LUMO energy level of the organic compound layer having the largest weight ratio.

[0099] Here, the closer the HOMO energy level and LUMO energy level are to the vacuum level, the higher they are described as being. The LUMO energy level of the charge generation layer being lower than the HOMO energy level of the hole transport layer means that the LUMO energy level of the charge generation layer is farther from the vacuum level than the HOMO energy level of the hole transport layer.

[0100] In this specification, the HOMO energy level and the LUMO energy level can be calculated using molecular orbital calculations. The molecular orbital calculations may be performed using density functional theory (DFT) or the like, using the B3LYP functional and the 6-31G* basis function or the like.The molecular orbital calculation can be carried out, for example, using Gaussian09 (Gaussian09, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasagawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2010.).

[0101] The HOMO energy level and LUMO energy level herein can be calculated using the ionization potential and band gap. The HOMO energy level can be estimated by measuring the ionization potential. The ionization potential can be measured using a measurement device such as an AC-3 after dissolving the compound to be measured in a solvent such as toluene or after forming a vapor-deposited film of the compound to be measured on a substrate such as glass. The band gap can be measured by dissolving the compound to be measured in a solvent such as toluene and irradiating it with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum of the excitation light. Alternatively, the compound to be measured can be vapor-deposited on a substrate such as glass and irradiating the vapor-deposited film with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum where the vapor-deposited film absorbs excitation light.

[0102] The LUMO energy level can be calculated using the band gap and the ionization potential value. The LUMO energy level can be estimated by subtracting the ionization potential value from the band gap.

[0103] The LUMO energy level can also be estimated from the reduction potential. For example, the one-electron reduction potential is estimated using CV (cyclic volmetry) measurements. CV measurements can be performed, for example, in a 0.1 M tetrabutylammonium perchlorate DMF solution using an Ag / Ag+ reference electrode, a Pt counter electrode, and a glassy carbon working electrode. The LUMO energy level can be estimated by adding -4.8 eV, the difference between the reduction potential of the obtained compound and the reduction potential of ferrocene.

[0104] In an organic light-emitting device according to one embodiment of the present invention, when the organic compound according to the present invention is contained in the light-emitting layer, the light-emitting layer may be a layer consisting solely of the organic compound according to the present invention, or may be a layer consisting of the organic compound according to the present invention and other compounds. Here, when the light-emitting layer is a layer consisting of the organic compound according to the present invention and other compounds, the organic compound according to the present invention may be used as a host material or a guest material of the light-emitting layer. It may also be used as an assist material that can be contained in the light-emitting layer. Here, the host material is also referred to as a "host" or "first compound" and is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. The guest material is also referred to as a "guest," "dopant material," "dopant," or "third compound," and is a compound that has a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer and is responsible for the primary emission of light. Therefore, the guest material is sometimes also referred to as an emitting material. The assist material is also referred to as an "assist" or "second compound," and is a compound that has a mass ratio smaller than that of the host material among the compounds constituting the light-emitting layer and assists the emission of the guest material. The assist material is also referred to as a second host.

[0105] Here, the lowest excited singlet energy of the host material is S1(H), the lowest excited singlet energy of the guest material is S1(D), and the lowest excited singlet energy of the assist material is S1(A). The guest material may be considered to be the organic compound according to the present invention. In this case, the organic light-emitting element according to this embodiment preferably satisfies S1(H)>S1(D) or S1(H)>S1(A)>S1(D). When the lowest excited singlet energy of the compound contained in the organic light-emitting element according to this embodiment satisfies the above relationship, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting element with superior luminous efficiency.

[0106] When the organic compound according to the present invention is used as a guest material in the light-emitting layer, the concentration of the guest material may be from 0.01% by mass to less than 50% by mass, preferably from 0.01% by mass to 10% by mass, and more preferably from 0.01% by mass to 5% by mass, based on the total mass of the light-emitting layer.

[0107] When the light-emitting layer further contains an assist material, the content of the assist material may be 1% by mass or more and less than 50% by mass, and preferably 10% by mass or more and less than 50% by mass, based on the total mass of the light-emitting layer. The content of the guest may be 0.01% by mass or more and 20% by mass, and preferably 0.01% by mass or more and 5% by mass or less.

[0108] The present inventors have conducted various studies and found that when the organic compound according to the present invention is used as a host material or guest material for the light-emitting layer, particularly as a guest material for the light-emitting layer, an element exhibiting high efficiency and high luminance light output and extremely high durability can be obtained. This light-emitting layer may be a single layer or multiple layers, and by including a light-emitting material having another luminescent color, it is possible to mix the color with the blue light emitted by this embodiment. "Multiple layers" refers to a state in which the light-emitting layer and another luminescent layer are stacked. In this case, the luminescent color of the organic light-emitting element is not limited to blue. More specifically, it may be white or a neutral color. In the case of white, the other luminescent layer emits a color other than blue, i.e., red or green. Furthermore, the film is formed by vapor deposition or coating. Details of this will be explained in detail in the examples below.

[0109] The organic compound according to the present invention can be used as a constituent material of an organic compound layer other than the light-emitting layer that constitutes the organic light-emitting device according to this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to blue. More specifically, it may emit white light or an intermediate color.

[0110] (3) Other Compounds In addition to the organic compound according to the present invention, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host materials, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may also be used together as needed. Examples of these compounds are listed below.

[0111] As the hole injection / transport material, a material with high hole mobility is preferred, facilitating the injection of holes from the anode and transporting the injected holes to the light-emitting layer. Furthermore, a material with a high glass transition temperature is preferred to suppress crystallization of organic compounds in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole injection / transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above-mentioned hole injection / transport materials are also suitable for use in electron blocking layers. Furthermore, when the hole injection layer is prepared by a coating method, a mixture of polyethylenedioxythiophene and polystyrene sulfonic acid (PEDOT:PSS), which is commonly used as a hole injection material, may also be used. Specific examples of compounds that can be used as hole injection / transport materials are listed below, but of course, the present invention is not limited to these.

[0112]

[0113] Among the hole injection and transport materials listed above, HT16 to HT18 can reduce the driving voltage when used in a layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2 to HT7, HT10, HT12, and HT22 to HT28 may be used in an organic compound layer adjacent to HT16. Hole-transporting polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinyl carbazole (PVK), and derivatives thereof may also be used. In addition, inorganic insulator layers such as SiO2 and SiN, and organic silicon polymers such as siloxane may also be used. Furthermore, multiple materials may be used in a single organic compound layer.

[0114] Examples of light-emitting materials primarily involved in light-emitting function include donor-acceptor organic compounds, boron-containing complexes, indocarbazole fused ring compounds, fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Furthermore, when preparing a light-emitting layer by a coating method, polymer compounds with luminescent properties are primarily used. This is because polymer compounds are highly amorphous and therefore less likely to crystallize than low-molecular-weight compounds. Specific examples of materials that can be used include polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinyl carbazole (PVK), and derivatives of these.

[0115] Specific examples of compounds that can be used as light-emitting materials are shown below, but the present invention is not limited to these.

[0116]

[0117]

[0118] Specific examples of compounds that can be used as the light-emitting layer host or light-emitting assist dopant contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0119]

[0120] The host material of EM1 to EM47 may be a hydrocarbon compound having a condensed polycyclic hydrocarbon group, specifically EM1 to EM26, EM46, and EM47.

[0121] The electron transporting material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transporting material. Examples of materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transporting materials are also suitable for use in hole-blocking layers.

[0122] Specific examples of compounds that can be used as electron transporting materials are shown below, but the present invention is not limited to these.

[0123]

[0124] The electron injection material can be arbitrarily selected from those that allow easy electron injection from the cathode, and is selected in consideration of the balance with hole injection properties, etc. Organic compounds include n-type dopants and reducing dopants. Examples include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives.

[0125] It can also be used in combination with the above electron transporting material.

[0126] (4) Configuration of the Organic Light-Emitting Device Hereinafter, the components that make up the organic light-emitting device of this embodiment will be described.

[0127] The organic light-emitting element is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate. A protective layer, a color filter, a microlens, etc. may be provided on the second electrode. When a color filter is provided, a planarizing layer may be provided between the color filter and the protective layer. The planarizing layer may be made of an acrylic resin, etc. The same applies when a planarizing layer is provided between the color filter and the microlens.

[0128] [Substrate] Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. Furthermore, the substrate may be provided with a switching element such as a transistor and wiring, and an insulating layer thereon. The insulating layer may be made of any material as long as it can form a contact hole so that wiring can be formed between the first electrode and the insulating layer, and can ensure insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0129] [Electrodes] A pair of electrodes can be used. The pair of electrodes is a first electrode and a second electrode. Specifically, the pair of electrodes may be an anode and a cathode. When an electric field is applied in the direction in which the organic light-emitting element emits light, the electrode with a higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.

[0130] The anode material should have as large a work function as possible. Examples of such materials include simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures containing these metals, alloys of these metals, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and zinc indium oxide. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0131] These electrode materials may be used alone or in combination of two or more. The anode may be composed of one layer or multiple layers.

[0132] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without functioning as an electrode. When used as a transparent electrode, transparent conductive oxide layers such as indium tin oxide (ITO) and indium zinc oxide can be used, but are not limited to these. Photolithography techniques can be used to form the electrode.

[0133] The cathode material preferably has a low work function. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and metals such as aluminum, titanium, manganese, silver, lead, and chromium, as well as mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, and zinc-silver can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials can be used alone or in combination. The cathode can have either a single-layer or multi-layer structure. Among these, silver is preferred, and a silver alloy is even more preferred to reduce silver aggregation. The alloy ratio is not critical as long as silver aggregation can be reduced. For example, the silver:other metal ratio can be 1:1, 3:1, or the like.

[0134] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but DC and AC sputtering methods are more preferable because they provide good film coverage and make it easier to reduce resistance.

[0135] [Organic Compound Layer] The organic compound layer may be formed as a single layer or as multiple layers. When multiple layers are present, they may be called hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer depending on their functions. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms or inorganic compounds. For example, the organic compound layer may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, or the like. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0136] The organic compound layers (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 device according to this embodiment are formed by the method shown below.

[0137] The organic compound layer constituting the organic light-emitting element according to this embodiment can be formed by a dry process such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively, instead of the dry process, a wet process can be used in which a compound is dissolved in an appropriate solvent and a layer is formed by a known coating method (for example, spin coating, dipping, casting, LB method, inkjet method, etc.).

[0138] Here, forming a layer by a vacuum deposition method, a solution coating method, etc. makes it difficult for crystallization to occur and provides excellent stability over time. When forming a film by a coating method, it is also possible to form a film by combining with an appropriate binder resin.

[0139] Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0140] These binder resins may be used singly or in combination as homopolymers or copolymers, and may further contain known additives such as plasticizers, antioxidants, and ultraviolet absorbers, if necessary.

[0141] [Protective Layer] A protective layer may be provided on the cathode. For example, by adhering glass provided with a moisture absorbent on the cathode, the intrusion of water and the like into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water and the like into the organic compound layer. For example, after forming the cathode, the cathode may be transported to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm may be formed by a CVD method to serve as a protective layer. A protective layer may be provided using atomic layer deposition (ALD) after the CVD film formation. The material of the film formed by the ALD method is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed on the film formed by the ALD method by a CVD method. The film formed by the ALD method may have a smaller thickness than the film formed by the CVD method. Specifically, the thickness of the film formed by the ALD method may be 50% or less, or even 10% or less, of the thickness of the film formed by the CVD method.

[0142] [Color Filter] A color filter may be provided on the protective layer. For example, a color filter taking into consideration the size of the organic light-emitting element may be provided on a separate substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using photolithography technology. The color filter may be made of a polymer.

[0143] [Planarization Layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing the unevenness of the underlying layer. It may also be called a material resin layer without limiting its purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but is preferably a high molecular weight.

[0144] The planarizing layer may be provided above or below the color filter, and may be made of the same or different materials, such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0145] [Microlens] The organic light-emitting element according to this embodiment may have an optical component such as a microlens on the light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be used to increase the amount of light extracted from the organic light-emitting element and to control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be determined in the same way in any cross-sectional view. In other words, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the semicircle is the vertex of the microlens.

[0146] It is also possible to define the midpoint of the microlens. In the cross section of the microlens, a line segment is imaginary, from the point where one arc shape starts to the point where another arc shape starts, and the midpoint of this line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0147] [Counter Substrate] An counter substrate may be provided on the planarization layer. The counter substrate is called a counter substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is defined as a first substrate, the counter substrate may be a second substrate.

[0148] [Pixel Circuit] The light-emitting device may have a pixel circuit connected to the light-emitting element. The pixel circuit may be an active matrix type that controls the emission of the first light-emitting element and the second light-emitting element independently. The active matrix type circuit may be voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission brightness of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0149] The light-emitting device has a display region and a peripheral region arranged around the display region. The display region has pixel circuits, and the peripheral region has a display control circuit. The mobility of a transistor constituting the pixel circuit may be lower than the mobility of a transistor constituting the display control circuit.

[0150] The slope of the current-voltage characteristics of the transistors that make up the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistors that make up the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics.

[0151] The transistors that make up the pixel circuit are transistors connected to light-emitting elements such as the first light-emitting element.

[0152] [Pixels] The organic light emitting device has a plurality of pixels. Each pixel has sub-pixels that emit different colors. The sub-pixels may emit, for example, RGB colors.

[0153] The pixel emits light from an area called the pixel aperture. This area is the same as the first area. The pixel aperture may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc.

[0154] The distance between the subpixels may be 10 μm or less, and specifically may be 8 μm, 7.4 μm, or 6.4 μm.

[0155] The pixels may be arranged in a known manner in a plan view. For example, they may be in a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in a plan view may be any known shape. For example, they may be rectangular, quadrilaterals such as diamonds, or hexagons. Of course, a shape that is close to a rectangle, rather than an exact shape, is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0156] (5) Uses of the Organic Light-Emitting Device According to the Present Embodiment The organic light-emitting device according to the present embodiment can be used as a component of a display device or a lighting device. Other uses include an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, and a light-emitting device having a white light source and a color filter.

[0157] The display device may be an image information processing device that has an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., has an information processing unit that processes the input information, and displays the input image on the display unit.

[0158] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. The display device may also be used in the display unit of a multifunction printer.

[0159] Next, the display device according to this embodiment will be described with reference to the drawings.

[0160] 1A and 1B are cross-sectional views showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin film transistor (TFT).

[0161] 1A shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel includes sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The emitted colors may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the sub-pixels may be selectively transmitted or color-converted using a color filter or the like. Each sub-pixel includes a reflective electrode 2, which serves as a first electrode, on an interlayer insulating layer 1; an insulating layer 3 covering the edge 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.

[0162] A transistor and a capacitor element may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0163] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edges of the first electrodes and surrounds the first electrodes. The portions where the insulating layer is not provided are in contact with the organic compound layer 4 and become light-emitting regions.

[0164] 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 .

[0165] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0166] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is illustrated as a single layer, it may be a multi-layer structure. Each layer may include an inorganic compound layer and an organic compound layer.

[0167] The color filters 7 are divided into 7R, 7G, and 7B depending on their colors. The color filters may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters. The color filters may be formed on a protective layer 6. Alternatively, the color filters may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0168] The display device 100 in FIG. 1B includes an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided with an insulating layer 12 on top of it. An active element 18 such as a TFT is disposed on the insulating layer, along with a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element. The active element 18 also includes the semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is disposed on top of the active element 18. An anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film.

[0169] Note that the method of electrical connection between the electrodes (anode, cathode) included in the organic light-emitting element 26 and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the mode shown in FIG. 1B. That is, it is sufficient that either one of the anode or the cathode is electrically connected to either one of the TFT source electrode or the drain electrode. TFT refers to a thin-film transistor.

[0170] In the display device 100 of FIG. 1B, the organic compound layer is illustrated as if it were a single layer, but the organic compound layer 22 may be a plurality of layers. On the cathode 23, a first protective layer 24 and a second protective layer 25 for reducing the deterioration of the organic light-emitting element are provided.

[0171] In the display device 100 of FIG. 1B, a transistor is used as the switching element, but other switching elements may be used instead.

[0172] Also, the transistor used in the display device 100 of FIG. 1B is not limited to a transistor using a single-crystalline silicon wafer, and may be a thin-film transistor having an active layer on an insulating surface of a substrate. Examples of the active layer include non-single-crystalline silicon such as single-crystalline silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystalline oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Note that the thin-film transistor is also called a TFT element.

[0173] The transistor included in the display device 100 of FIG. 1B may be formed in a substrate such as a Si substrate. Here, forming in the substrate means manufacturing a transistor by processing the substrate itself such as a Si substrate. That is, having a transistor in the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0174] The organic light-emitting element according to this embodiment has its emission brightness controlled by a TFT, which is an example of a switching element. By providing multiple organic light-emitting elements on a surface, an image can be displayed based on the emission brightness of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor formed from low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also be referred to as "inside the substrate." Whether to provide a transistor within the substrate or to use a TFT is determined by the size of the display unit. For example, for a display unit of about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0175] 2 is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The display panel 1005 may include an organic light-emitting element according to this embodiment. Flexible printed circuits FPCs 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005, respectively. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position even if the display device is a portable device.

[0176] The display device according to this embodiment may have color filters having red, green, and blue colors, which may be arranged in a delta arrangement.

[0177] The display device according to the present embodiment may be used as a display unit of a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

[0178] The display device according to this embodiment may be used as a display unit of an imaging device having an imaging element that receives light. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0179] 3A is a schematic diagram illustrating an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 and the rear display 1102 may include the organic light-emitting element according to this embodiment. In this case, the viewfinder 1101 and the rear display 1102 may display not only the image to be captured, but also environmental information, imaging instructions, and the like. The environmental information may include the intensity of external light, the direction of external light, the speed at which the subject is moving, the possibility that the subject will be blocked by an obstruction, and the like.

[0180] Since the optimum timing for capturing an image is very short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element according to this embodiment, because the organic light-emitting element has a fast response speed.

[0181] The imaging device 1100 may further include an optical unit (not shown). The optical unit may include a single lens or multiple lenses, which form an image on an imaging element housed in a housing 1104. The focus of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may also be called a photoelectric conversion device. Instead of sequentially capturing images, the photoelectric conversion device may include an imaging method that detects the difference from the previous image, or a method of cutting out an image from a constantly recorded image.

[0182] FIG. 3B is a schematic diagram illustrating an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit may be a biometric recognition unit that recognizes a fingerprint to perform operations such as unlocking. An electronic device having a communication unit can also be called a communication device. The electronic device may further have a camera function by including a lens and an image sensor. An image captured by the camera function is displayed on the display unit. Examples of the electronic device include a smartphone and a laptop computer.

[0183] 4A and 4B are schematic diagrams illustrating an example of a display device according to this embodiment. Fig. 4A illustrates a display device such as a television monitor or a PC monitor. The display device 1300 includes a housing 1301 and a display unit 1302. The display unit 1302 may include the organic light-emitting element according to this embodiment.

[0184] The display device 1300 may include a housing 1301 and a base 1303 that supports a display portion 1302. The base 1303 is not limited to the form shown in Fig. 4A. The bottom side of the housing 1301 may also serve as the base.

[0185] The housing 1301 and the display unit 1302 may be curved. The radius of curvature may be 5000 mm or more and 6000 mm or less.

[0186] FIG. 4B is a schematic diagram illustrating another example of a display device according to the present embodiment. The display device 1310 in FIG. 4B is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include an organic light-emitting element according to the present embodiment. The first display unit 1311 and the second display unit 1312 may be a single, seamless display device. The first display unit 1311 and the second display unit 1312 can be separated by the bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may display a single image.

[0187] FIG. 5A is a schematic diagram illustrating an example of a lighting device according to this embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may include an organic light-emitting element according to this embodiment. The lighting device 1400 may include an optical film 1404 to improve the color rendering properties of the light source. The lighting device 1400 may also include a light diffusion unit 1405 to effectively diffuse light from the light source. By including the light diffusion unit 1405, the lighting device 1400 can deliver light over a wide range. The optical film 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting device. If necessary, a cover may be provided on the outermost surface.

[0188] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white, daylight white, or any other color from blue to red. The lighting device according to this embodiment may have a dimming circuit that dims these colors. The lighting device according to this embodiment may also have a power supply circuit that is connected to the organic light-emitting element according to this embodiment. The power supply circuit may be a circuit that converts AC voltage to DC voltage. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device according to this embodiment may further have a color filter.

[0189] The lighting device according to this embodiment may also include a heat dissipation section, which dissipates heat from within the device to the outside and is made of a material such as metal or ceramic with high thermal conductivity.

[0190] FIG. 5B is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has a tail lamp, which is an example of a lamp. The automobile 1500 has a tail lamp 1501 and a body 1503, and the tail lamp may be turned on when the brakes are applied, for example. The body 1503 may also be referred to as a vehicle body. The automobile 1500 may have a window 1502 attached to the body 1503. The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp may have a protective member that protects the light source. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. A furandicarboxylic acid derivative, an acrylonitrile derivative, or the like may be mixed with polycarbonate.

[0191] The window 1502 may be a transparent display other than a window for checking the front and rear of the vehicle. The transparent display may include the organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element according to the present invention are made of transparent materials.

[0192] The moving body according to this embodiment includes one or both of a driving force generating unit that generates a driving force that is mainly used to move the moving body, and a rotating body that is mainly used to move the moving body. The driving force generating unit may be an engine, a motor, etc. The rotating body may be a tire, a wheel, a ship's screw, a propeller of an aircraft, etc. Specifically, the moving body may be a bicycle, an automobile, a train, a ship, an aircraft, a drone, etc. The moving body may have a body and a lighting device provided on the body. The lighting device may emit light to indicate the position of the body.

[0193] 6A and 6B , application examples of the display devices of the above-described embodiments will be described. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, head-mounted displays, and smart contact lenses. A display device that can be used in a wearable device may include an imaging device that can photoelectrically convert visible light and a display device that can emit visible light.

[0194] 6A and 6B are schematic diagrams showing an example of glasses (smart glasses) according to this embodiment. Glasses 1600 (smart glasses) will be described using FIG. 6A . The glasses 1600 have a display unit on the rear side of lenses 1601. The display unit may have an organic light-emitting element according to the present invention. Furthermore, an imaging device 1602 such as a CMOS sensor or a SPAD may be provided on the front side of the lenses 1601.

[0195] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display unit. The control device 1603 also controls the operations of the image capture device 1602 and the display unit. The lens 1601 is formed with an optical system for condensing light from the image capture device 1602 and the display unit.

[0196] Using FIG. 6B , glasses 1610 (smart glasses) are described. The glasses 1610 include a control device 1612, which is provided with a display device having an organic light-emitting element according to the present invention. The control device 1612 may further include an imaging device corresponding to the imaging device 1602. A lens 1611 is formed with an optical system for projecting light emitted from the control device 1612, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operation of the imaging device and the display device. The control device may include a gaze detection unit that detects the wearer's gaze. Infrared light may be used for gaze detection. The infrared light emitting unit emits infrared light toward the eyeball of a user gazing at a displayed image. An imaging unit having a light receiving element detects the emitted infrared light reflected from the eyeball, thereby obtaining an image of the eyeball. By including a reduction unit that reduces light from the infrared light emitting unit to the display unit in a planar view, degradation of image quality is reduced.

[0197] The control device 1612 detects the user's line of sight with respect to the displayed image from the captured image of the eyeball obtained by capturing infrared light. Any known method can be applied to gaze detection using the captured image of the eyeball. As an example, a gaze detection method can be used based on a Purkinje image formed by reflection of irradiated light on the cornea.

[0198] More specifically, gaze detection processing is performed based on the pupil-corneal reflex method, which uses the pupil-corneal reflex method to generate a gaze vector representing the orientation (rotation angle) of the eyeball based on the pupil image and Purkinje image contained in the captured image of the eyeball, thereby detecting the user's gaze.

[0199] The display device according to this embodiment may have an imaging device having a light receiving element, and may control the image displayed on the display device based on information about the user's line of sight from the imaging device.

[0200] Specifically, the display device determines a first field of view area where the user gazes and a second field of view area other than the first field of view area based on the line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0201] The display area has a first field of view area and a second field of view area different from the first field of view area, and a high-priority area is determined from the first field of view area and the second field of view area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. The resolution of the high-priority area may be controlled to be higher than the resolution of areas other than the high-priority area. In other words, the resolution of an area with a relatively low priority may be lowered.

[0202] In addition, AI may be used to determine the first field of view area or the field of view area with high priority. The AI ​​may be a model configured to estimate the angle of gaze and the distance to the object in the line of sight from the image of the eyeball, using as training data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI ​​may be included in the display device, the imaging device, or an external device. When the external device includes AI, it can be preferably applied to smart glasses that further include an imaging device that captures images of the outside. The smart glasses can display captured external information in real time.

[0203] 7A is a schematic diagram showing an example of an image forming apparatus according to the present embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27. The exposure light source 28 may include an organic light-emitting element according to the present embodiment. The developing unit 31 includes toner and the like. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a storage medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0204] 7B and 7C are diagrams showing an exposure light source 28 and are schematic diagrams illustrating a state in which multiple light-emitting units 36 are arranged on a long substrate. Arrow 37 indicates the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the axis direction about which the photoconductor 27 rotates. This direction can also be referred to as the long axis direction of the photoconductor 27. FIG. 7B shows a configuration in which the light-emitting units 36 are arranged along the long axis of the photoconductor 27. FIG. 7C shows a different configuration from FIG. 7B, in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are arranged at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged at intervals. In the second column, the light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. In other words, multiple light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in FIG. 7C can also be described as a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0205] As described above, by using a device using the organic light-emitting element according to this embodiment, it is possible to provide a stable display with good image quality even over a long period of time.

[0206] The present invention will be described below with reference to examples, although the present invention is not limited to these examples.

[0207] Example 1 (Synthesis of Compound A-1) Compound A-1 was synthesized according to the following synthetic route.

[0208]

[0209] Intermediate 1 (0.300g), (3-cyanophenyl)boronic acid (0.225g), Pd ２ (dba) ３ (0.014 g), XPhos (0.015 g), sodium carbonate (0.240 g), toluene (45 mL), tetrahydrofuran (45 mL), and water (15 mL) were added, and the mixture was stirred at 80°C for 16 hours. Extraction with toluene was performed, and purification was carried out using an organic solvent GPC column (JAIGEL-2H-40 manufactured by Japan Analytical Industry Co., Ltd., eluent: chloroform), to obtain 238 mg of compound A-1 as a yellow powder. A solution obtained by adding THF to this yellow powder was subjected to mass analysis by UPLC (Ultra High Performance Liquid Chromatography)-MS, and the compound was identified (m / z = 830.435, C ６０ H ５４ N ４ ).

[0210] Example 2 (Synthesis of Compound A-2) Compound A-2 was synthesized according to the following synthetic route.

[0211]

[0212] Intermediate 1 (0.400g), (4-cyanophenyl)boronic acid (0.600g), Pd(dppf)CH ２ Cl ２ (0.033 g), sodium carbonate (0.323 g), toluene (100 mL), dioxane (100 mL), and water (30 mL) were added, and the mixture was stirred at 150°C for 16 hours. The mixture was extracted with toluene and purified using an organic solvent GPC column (JAIGEL-2H-40 manufactured by Japan Analytical Industry Co., Ltd., eluent: chloroform), to obtain 288 mg of compound A-2 as a yellow powder. The solution obtained by adding THF to this yellow powder was subjected to mass analysis by UPLC (Ultra High Performance Liquid Chromatography)-MS and identified (m / z = 830.435, C ６０ H ５４ N４ ).

[0213] Example 3 (Fabrication and Evaluation of Organic Light-Emitting Device) In Example 3, Compound A-1 was used as a guest material in the light-emitting layer. An organic light-emitting device having 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, and a cathode provided in this order on a substrate was fabricated by the method described below.

[0214] A glass substrate was used as a transparent conductive support substrate (ITO substrate) by forming a 100 nm thick ITO film as an anode by sputtering. The glass substrate with the ITO film was then ultrasonically cleaned with acetone and isopropyl alcohol (IPA) in succession, then boiled and cleaned with IPA, and then dried. It was then UV / ozone cleaned. The glass substrate thus treated was used as a transparent conductive support substrate.

[0215] Next, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and a metal electrode layer were formed on the substrate. －５ The film was continuously formed by vacuum deposition using resistance heating in a vacuum chamber at 1000 Pa. At this time, the electrode area was 3 mm ２ The layer structure is shown below.

[0216]

[0217] Next, in order to prevent deterioration of the organic light emitting element due to absorption of moisture, the organic light emitting element was covered with a protective glass plate in a dry air atmosphere and sealed with an acrylic resin adhesive. In this way, an organic light emitting element was obtained.

[0218] The characteristics of the obtained organic light-emitting device were measured and evaluated. ２ The external quantum efficiency (EQE) of the organic light-emitting device at this temperature was 4.46%.

[0219] Furthermore, the current density is 20 mA / cm ２ A continuous driving test was carried out at 100°C, and the time (LT80) when the luminance degradation rate reached 20% from the initial luminance was measured. When the time when the luminance degradation rate of Comparative Example 1 reached 20% was set to 1.0, the relative value of LT80 of this example was 2.41.

[0220] The half-width of the emission spectrum was determined to be 29 nm.

[0221] In this example, the measuring device was a DC voltage / current source / monitor 6253 manufactured by ADC Corporation to measure the current-voltage characteristics, and a spectroradiometer SR-LEDW manufactured by Topcon Corporation to measure the luminance.

[0222] Example 4, Comparative Example 1 (Preparation and Evaluation of Organic Light-Emitting Device) An organic light-emitting device was prepared in the same manner as in Example 3, except that compound A-1 was changed to compound A-2, and was designated as Example 4. Furthermore, an organic light-emitting device was prepared in the same manner as in Example 3, except that compound A-1 was changed to compound Ref-1, and was designated as Comparative Example 1. The characteristics of the prepared organic light-emitting device were measured and evaluated in the same manner as in Example 3. The results are shown in Table 7.

[0223]

[0224] As can be seen from Table 7, the organic compounds according to the present invention exhibited superior device lifetimes compared to the comparative compound Ref-1. This is thought to be because the organic compounds according to the present invention have electron-withdrawing groups, which result in a lower HOMO (farther from the vacuum level). Furthermore, the organic compounds according to the present invention exhibited a smaller full width at half maximum than the comparative compound Ref-1.

[0225] As described above, the organic compound according to the present invention is an organic compound having excellent oxidation stability. Therefore, by using the organic compound according to the present invention in an organic light-emitting element, an organic light-emitting element having excellent element life can be provided. Furthermore, by using an organic compound having excellent oscillator strength among the organic compounds according to the present invention in an organic light-emitting element, an organic light-emitting element having excellent quantum yield (luminous efficiency) can be provided. Furthermore, by using an organic compound having excellent color purity among the organic compounds according to the present invention in an organic light-emitting element, an organic semiconductor that emits light having even more excellent color purity can be provided.

[0226] The present invention can also have the following configuration.

[0227] (Configuration 1) An organic compound represented by formula (1):

[0228]

[0229] In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having from 6 to 50 carbon atoms and substituted or unsubstituted heterocyclic groups having from 3 to 50 carbon atoms. When rings A to C have a substituent, the substituent is a deuterium atom, an alkyl group, an aryl group, a heterocyclic group, a silyl group, an amino group, or a cyano group.

[0230] EWG is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one or more electron-withdrawing groups.

[0231] n is an integer of 1 or more.

[0232] (Configuration 2) The organic compound according to Configuration 1, wherein in formula (1), the electron-withdrawing group is a trifluoromethyl group, a trichloromethyl group, a nitro group, a cyano group, an aldehyde group, a ketone group, an ester group, a carboxylic acid group, a sulfonyl group, a sulfonic acid group, a pyridyl group, a triazinyl group, or a halogen atom.

[0233] (Configuration 3) The organic compound according to configuration 1 or 2, wherein in formula (1), the electron-withdrawing group is a trifluoromethyl group, a cyano group, or a fluorine atom.

[0234] (Structure 4) In the formula (1), EWG is an aryl group having 6 to 20 carbon atoms and having at least one electron-withdrawing group, or a heterocyclic group having 3 to 17 carbon atoms and having at least one electron-withdrawing group. The organic compound according to any one of Structures 1 to 3.

[0235] (Configuration 5) The organic compound according to any one of Configurations 1 to 4, wherein in formula (1), the aryl group possessed by EWG is benzene.

[0236] (Structure 6) In the formula (1), rings A to C are a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heterocyclic group having 3 to 17 carbon atoms.

[0237] (Configuration 7) The organic compound according to any one of configurations 1 to 6, wherein in formula (1), ring A is a benzene skeleton or a naphthalene skeleton, and n is an integer of 1 or more and 4 or less.

[0238] (Configuration 8) The organic compound according to any one of Configurations 1 to 7, wherein in formula (1), ring B is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

[0239] (Configuration 9) The organic compound according to any one of Configurations 1 to 8, wherein in formula (1), ring C is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

[0240] (Configuration 10) An organic compound represented by formula (2) or formula (3).

[0241]

[0242] In formula (2), R １ ~R １６ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R１０ and R １１ , R １２ and R １３ , R １３ and R １４ may be bonded to each other to form a ring. １５ and R １６ At least one of the groups is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

[0243] In formula (3), R ２１ ~R ３８ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２６ and R ２７ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and R ３１ , R ３２ and R ３３ , R ３３ and R ３４ may be bonded to each other to form a ring. ３５ ~R ３８ At least one of the groups is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

[0244] (Configuration 11) The organic compound according to configuration 10, wherein in formulas (2) and (3), the electron-withdrawing group is a trifluoromethyl group, a trichloromethyl group, a nitro group, a cyano group, an aldehyde group, a ketone group, an ester group, a carboxylic acid group, a sulfonyl group, a sulfonic acid group, a pyridyl group, a triazinyl group, or a halogen atom.

[0245] (Configuration 12) The organic compound according to configuration 10 or 11, wherein in formula (2) and (3), the electron-withdrawing group is a trifluoromethyl group, a cyano group, or a fluorine atom.

[0246] (Structure 13) The organic compound according to any one of Structures 10 to 12, characterized in that in formulas (2) and (3), the ring is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms or a substituted or unsubstituted heterocyclic group having 3 to 12 carbon atoms.

[0247] (Structure 14) The organic compound according to any one of Structures 10 to 13, wherein in the formulas (2) and (3), the ring is a substituted or unsubstituted benzofuran skeleton or a substituted or unsubstituted benzothiophene skeleton.

[0248] (Structure 15) An organic light-emitting element having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer contains the organic compound according to any one of Structures 1 to 14.

[0249] (Configuration 16) The organic light-emitting element according to Configuration 15, wherein the organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound.

[0250] (Structure 17) The organic light-emitting element according to Structure 16, wherein the light-emitting layer further comprises a first compound, and the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the organic compound.

[0251] (Configuration 18) The organic light-emitting device according to Configuration 17, wherein the first compound is a hydrocarbon compound having a condensed polycyclic hydrocarbon group.

[0252] (Structure 19) The organic light-emitting element according to Structure 17 or 18, wherein the light-emitting layer further comprises a second compound, and the lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the organic compound and lower than the lowest excited singlet energy of the first compound.

[0253] (Configuration 20) A display device having a plurality of pixels, at least one of the plurality of pixels having the organic light-emitting element according to any one of Configurations 15 to 19 and a transistor connected to the organic light-emitting element.

[0254] (Configuration 21) A photoelectric conversion device comprising: an imaging element that receives light; and a display unit that displays an image captured by the imaging element, wherein the display unit has the organic light-emitting element according to any one of Configurations 15 to 19.

[0255] (Configuration 22) An image display device comprising: a display section having the organic light-emitting element according to any one of Configurations 15 to 19; and a housing in which the display section is provided.

[0256] (Configuration 23) An electronic device comprising: a display unit having the organic light-emitting element according to any one of Configurations 15 to 19; a housing in which the display unit is provided; and a communication unit provided in the housing and communicating with an external device.

[0257] (Configuration 24) A wearable device comprising: a display unit having the organic light-emitting element according to any one of Configurations 15 to 19; an optical system that focuses light from the display unit; and a control device that controls display on the display unit.

[0258] (Configuration 25) A lighting device comprising: a light source having the organic light-emitting element according to any one of Configurations 15 to 19; and a housing in which the light source is provided.

[0259] (Configuration 26) A moving body comprising: a lighting fixture having the organic light-emitting element according to any one of Configurations 15 to 19; and a vehicle on which the lighting fixture is provided.

[0260] (Configuration 27) An image forming apparatus comprising: a photosensitive member; and an exposure light source for exposing the photosensitive member, wherein the exposure light source comprises the organic light-emitting element according to any one of Configurations 15 to 19.

[0261] The present invention is not limited to the above-described embodiments, and various modifications and variations can be made without departing from the spirit and scope of the present invention. Therefore, the following claims are appended to apprise the public of the scope of the present invention.

[0262] This application claims priority based on Japanese Patent Application No. 2023-145293, filed September 7, 2023, the entire contents of which are incorporated herein by reference.

[0263] REFERENCE SIGNS LIST 1 Interlayer insulating layer 2 Reflective electrode 3 Insulating layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color filter 10 Subpixel 11 Substrate 12 Insulating layer 13 Gate electrode 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrode 18 Thin film transistor 19 Insulating film 20 Contact hole 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting element 27 Photosensitive member 28 Exposure light source 29 Light 30 Charging section 31 Developing section 32 Transfer section 33 Transport section 34 Recording medium 35 Fixing section 36 Light-emitting section 37 First direction parallel to the major axis of the photosensitive member 40 Image forming apparatus 100 Display device 1000 Display device 1001 Upper cover 1002 Flexible printed circuit 1003 Touch panel 1004 Flexible printed circuit 1005 Display panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation unit 1104 Housing 1200 Electronic device 1201 Display unit 1202 Operation unit 1203 Housing 1300 Display device 1301 Frame 1302 Display unit 1303 Base 1310 Display device 1311 First display unit 1312 Second display unit 1313 Housing 1314 Bend point 1400 Illumination device 1401 Housing 1402 Light source 1403 Circuit board 1404 Optical film 1405 Light diffusion unit 1500 Automobile 1501 Tail lamp 1502 Window 1503 Vehicle body 1600 Smart glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart glasses 1611 Lens 1612 Control device

Claims

1. An organic compound represented by formula (1): In formula (1), rings A to C are each independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 50 carbon atoms and substituted or unsubstituted heterocyclic groups having 3 to 50 carbon atoms. When rings A to C have a substituent, the substituent is a deuterium atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heteroaryloxy group, a silyl group, an amino group, or a cyano group. EWG is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one or more electron-withdrawing groups. n is an integer of 1 or more.

2. The organic compound according to claim 1, characterized in that in formula (1), the electron-withdrawing group is a trifluoromethyl group, a trichloromethyl group, a nitro group, a cyano group, an aldehyde group, a ketone group, an ester group, a carboxylic acid group, a sulfonyl group, a sulfonic acid group, a pyridyl group, a triazinyl group, or a halogen atom.

3. The organic compound according to claim 1, characterized in that in formula (1), the electron-withdrawing group is a trifluoromethyl group, a cyano group, or a fluorine atom.

4. The organic compound according to claim 1, characterized in that in formula (1), EWG is an aryl group having 6 to 20 carbon atoms and at least one electron-withdrawing group, or a heterocyclic group having 3 to 17 carbon atoms and at least one electron-withdrawing group.

5. The organic compound according to claim 1, characterized in that in formula (1), the aryl group possessed by EWG is benzene.

6. The organic compound according to claim 1, characterized in that, in formula (1), rings A to C are a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 17 carbon atoms.

7. The organic compound according to claim 1, wherein in formula (1), ring A is a benzene skeleton or a naphthalene skeleton, and n is an integer of 1 or more and 4 or less.

8. The organic compound according to claim 1, wherein in formula (1), ring B is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

9. The organic compound according to claim 1, wherein in formula (1), ring C is a benzene skeleton, a benzofuran skeleton, or a benzothiophene skeleton.

10. An organic compound represented by formula (2) or formula (3). In formula (2), R １ ~R １６ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ５ and R ６ , R ６ and R ７ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １２ and R １３ , R １３ and R １４ may be bonded to each other to form a ring. １５ and R １６ At least one of R is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group. ２１ ~R ３８ are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２６ and R ２７ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and R ３１ , R ３２ and R ３３ , R ３３ and R ３４ may be bonded to each other to form a ring. ３５ ~R ３８ At least one of is an electron-withdrawing group, an aryl group having at least one electron-withdrawing group, or a heterocyclic group having at least one electron-withdrawing group.

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

12. The organic light-emitting device according to claim 11, wherein the organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound.

13. The organic light-emitting element according to claim 12, characterized in that the light-emitting layer further comprises a first compound, and the lowest excited singlet energy of the first compound is higher than the lowest excited singlet energy of the organic compound.

14. The organic light-emitting device according to claim 13, wherein the first compound is a hydrocarbon compound having a condensed polycyclic hydrocarbon group.

15. The organic light-emitting element described in claim 13, characterized in that the light-emitting layer further comprises a second compound, and the lowest excited singlet energy of the second compound is higher than the lowest excited singlet energy of the organic compound and lower than the lowest excited singlet energy of the first compound.

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

17. A photoelectric conversion device comprising an image sensor that receives light, and a display unit that displays an image captured by the image sensor, the display unit having an organic light-emitting element according to any one of claims 11 to 15.

18. An image display device comprising: a display section having an organic light-emitting element according to any one of claims 11 to 15; and a housing in which the display section is provided.

19. An electronic device comprising: a display unit having an organic light-emitting element according to any one of claims 11 to 15; a housing in which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

20. A wearable device comprising: a display unit having an organic light-emitting element according to any one of claims 11 to 15; an optical system for concentrating light from the display unit; and a control device for controlling the display of the display unit.

21. A lighting device comprising: a light source having an organic light-emitting element according to any one of claims 11 to 15; and a housing in which the light source is provided.

22. A moving object comprising a lighting device having an organic light-emitting element according to any one of claims 11 to 15, and a body on which the lighting device is mounted.

23. An image forming apparatus comprising: a photoconductor; and an exposure light source for exposing said photoconductor, said exposure light source comprising an organic light-emitting element according to any one of claims 11 to 15.

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