Organic compounds and organic light-emitting devices

Abstract

To provide an organic compound exhibiting a high oscillator strength. 【Solution means】A compound characterized by being represented by the general formula G1. TIFF2026093344000031.tif5278 (Ring C is an aromatic hydrocarbon ring or a heteroaromatic ring. A 11 to A 15 , A 21 to A 25 is CR A or N. R A is H or a substituent. X 1 and X 2 are O, S, Te, Se or NR B , R B is H or a substituent. Adjacent R A to each other, or adjacent R A and R B may combine to form a ring.)

Description

[Technical Field]

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

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

[0003] Incidentally, there has been a lot of effort to create compounds suitable for organic light-emitting devices. Non-patent document 1 describes C1 and C2 as heteroaromatic ring compounds.

[0004] [ka] [Prior art documents] [Non-patent literature]

[0005] [Non-Patent Document 1] Zhang, Y., Fukuma, S., Shang, R. et al. “Iron-catalysed C(sp2)-H activation for aza-annulation with alkynes on extended π-conjugated systems.” Nat.Synth(2024), 09 July 2024, 3, 1349-1359. [Overview of the project] [Problems that the invention aims to solve]

[0006] However, compound C1, described in Non-Patent Document 1, exhibits a small transition dipole moment because the orbital distribution of its HOMO (Highest Occupied Molecular Orbital) is not distributed throughout the entire molecule. Similarly, compound C2 exhibits a small transition dipole moment because the direction of the elongation of its conjugate length differs from the direction of its transition dipole moment. Since a smaller transition dipole moment corresponds to a smaller oscillator strength, compounds C1 and C2 have room for improvement in terms of oscillator strength.

[0007] This invention has been made in view of the above problems, and its purpose is to provide an organic compound with excellent luminescence efficiency. [Means for solving the problem]

[0008] The organic compound according to the present invention is characterized by being represented by the general formula G1.

[0009] [ka]

[0010] In general formula G1, ring C is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 5 to 50 carbon atoms.

[0011] A 11 Or A 15 , A 21 Or A 25 CR A R is independently selected from the group consisting of nitrogen atoms. Ais 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 alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted thioaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted thioheteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a nitro group. R A When there are a plurality of R A may be the same or different from each other.

[0012] X 1 and X 2 are independently selected from the group consisting of an oxygen atom, a sulfur atom, a tellurium atom, a selenium atom, and NR B R B is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted thioaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted thioheteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a nitro group. R B When there are a plurality of R B may be the same or different from each other.

[0013] Adjacent R A to each other, or adjacent R A and R B may combine to form a ring.

Advantages of the Invention

[0014] According to the present invention, it is possible to provide organic compounds with high oscillator strength. [Brief explanation of the drawing]

[0015] [Figure 1] (a) A schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention. (b) A schematic cross-sectional view showing an example of a display device using an organic EL element according to one embodiment of the present invention. [Figure 2] This is a schematic diagram illustrating an example of a display device according to one embodiment of the present invention. [Figure 3] (a) A schematic diagram showing an example of an imaging device according to one embodiment of the present invention. (b) A schematic diagram showing an example of an electronic device according to one embodiment of the present invention. [Figure 4] (a) A schematic diagram showing an example of a display device according to one embodiment of the present invention. (b) A schematic diagram showing an example of a foldable display device. [Figure 5] (a) A schematic diagram showing an example of a lighting device according to one embodiment of the present invention. (b) A schematic diagram showing an example of an automobile having a vehicle light fixture according to one embodiment of the present invention. [Figure 6] (a) A schematic diagram showing an example of a wearable device according to one embodiment of the present invention. (b) A schematic diagram showing an example of a wearable device according to one embodiment of the present invention, which includes an imaging device. [Figure 7] (a) A schematic diagram of a head-mounted display as a display device according to one embodiment of the present invention. (b) A schematic diagram showing an example in which a display device according to one embodiment of the present invention is connected to an external device. [Figure 8] (a) A schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. (b) A schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. (c) A schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. [Figure 9] This figure shows the HOMO orbital distribution, LUMO orbital distribution, and direction and magnitude of the transition dipole moment of the organic compound according to the present invention. [Figure 10]This figure shows the HOMO orbital distribution, LUMO orbital distribution, and direction and magnitude of the transition dipole moment of the organic compound in the comparative example. [Modes for carrying out the invention]

[0016] In this specification, halogen atoms include, but are not limited to, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0017] The alkyl group may be an alkyl group having 1 to 50 carbon atoms, an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or an alkyl group having 1 to 4 carbon atoms. Specifically, examples include, but are not limited to, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, secondary butyl group, octyl group, cyclohexyl group, tert-pentyl group, 3-methylpentan-3-yl group, 1-adamantyl group, and 2-adamantyl group.

[0018] The alkenyl group may be either an E-alkenyl group or a Z-alkenyl group. The E-alkenyl group and the Z-alkenyl group may have 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 8 carbon atoms.

[0019] The alkynyl group may be an alkynyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 10 carbon atoms, or an alkynyl group having 1 to 8 carbon atoms.

[0020] The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. Specifically, examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-octyloxy group, a benzyloxy group, etc.

[0021] A thioalkoxy group is a structure in which the oxygen atom that would normally substitute for an alkyl group in an alkoxy group is replaced by a sulfur atom. A thioalkoxy group may have 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 4 carbon atoms. Specifically, examples include, but are not limited to, thiomethoxy, thioethoxy, thiopropoxy, 2-ethyl-octylthio, and benzylthio groups.

[0022] The aryl group may be an aryl group having 6 to 50 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 18 carbon atoms, or an aryl group having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, anthranyl, perilenyl, chrysenyl, and fluoranthenyl groups.

[0023] A thioaryl group is a structure in which the oxygen atom bonded to the aryl group in an aryloxy group is replaced by a sulfur atom. Examples include, but are not limited to, the thiophenoxy group.

[0024] Examples of aryloxy groups include, but are not limited to, phenoxy groups.

[0025] The heteroaryl group may be a heteroaryl group having 3 to 50 carbon atoms, a heteroaryl group having 5 to 50 carbon atoms, a heteroaryl group having 3 to 24 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, a heteroaryl group having 5 to 18 carbon atoms, or a heteroaryl group having 5 to 12 carbon atoms. Specifically, examples include, but are not limited to, pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, and phenanthrolyl groups.

[0026] A thioheteroaryl group is a heteroaryloxy group in which the oxygen atom bonded to the heteroaryl group is replaced by a sulfur atom. Examples include, but are not limited to, the thienylthio group.

[0027] Examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0028] Examples of silyl groups include, but are not limited to, trimethylsilyl and triphenylsilyl groups.

[0029] 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 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, N-methylamino group, N-ethylamino group, N,N-dimethylamino group, N,N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N,N-dibenzyloamino group, anilino group, N,N-diphenylamino group, N,N-dinaphthylamino group, N,N-difluorenylamino group, N-phenyl-N-tolylamino group, N,N-ditolylamino group, N-methyl-N-phenylamino group, N,N-dianisorylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tert-butylphenyl)amino group, N-phenyl-N-(4-trifluoromethylphenyl)amino group, N-piperidyl group, etc.

[0030] The aromatic hydrocarbon ring may be an aromatic hydrocarbon ring having 6 to 50 carbon atoms, an aromatic hydrocarbon ring having 6 to 20 carbon atoms, an aromatic hydrocarbon ring having 6 to 18 carbon atoms, or an aromatic hydrocarbon ring having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, benzene, naphthalene, indene, fluorene, phenanthrene, triphenylene, pyrene, anthracene, perylene, chrysene, fluorantene, etc.

[0031] The heteroaromatic ring may be a heteroaromatic ring having 5 to 50 carbon atoms, a heteroaromatic ring having 5 to 24 carbon atoms, a heteroaromatic ring having 5 to 18 carbon atoms, or a heteroaromatic ring having 5 to 12 carbon atoms. Specifically, examples include, but are not limited to, pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, oxazoline, oxadiazoline, thiazoline, thiadiazoline, carbazole group, acridine, phenanthroline, etc.

[0032] The alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, thioalkoxy groups, aryl groups, thioaryl groups, aryloxy groups, heteroaryl groups, thioheteroaryl groups, heteroaryloxy groups, silyl groups, amino groups, aromatic hydrocarbon rings, and heteroaromatic rings may further contain substituents such as halogen atoms like fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl groups; alkoxy groups such as methoxy, ethoxy, and propoxy groups; amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino groups; aryloxy groups such as phenoxy; aryl groups such as phenyl and biphenyl; heteroaryl groups such as pyridyl and pyrrolyl groups; and cyano groups, but are not limited to these.

[0033] (1)Organic compounds The organic compound according to the present invention is characterized by being represented by the general formula G1.

[0034] [ka]

[0035] <Ring C> In general formula G1, ring C is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 5 to 50 carbon atoms. Ring C may be a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 5 to 12 carbon atoms, and may be a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 12 carbon atoms. Specifically, it may be benzene, naphthalene, anthracene, phenanthrene, furan, thiophene, benzofuran, benzothiophene, dibenzothiofuran, or dibenzothiophene, and is preferably benzene, naphthalene, anthracene, or phenanthrene, more preferably benzene or naphthalene, and more preferably benzene. When ring C is benzene or naphthalene, blue to green emission can be obtained. Furthermore, when ring C is benzene, blue emission with excellent color purity can be obtained, which is preferable.

[0036] 11 Or A 15 , A 21 Or A 25 > In general formula G1, A 11 Or A 15 , A 21 Or A 25 CR A R is independently selected from the group consisting of nitrogen atoms. A Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups.​A When there are multiple R A They may be the same or different.

[0037] R A This may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted thioalkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted thioaryl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted thioheteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, or a nitro group. A This may be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms, a thioaryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 3 to 13 carbon atoms, a triphenylsilyl group, an amino group having an alkyl group having 1 to 4 carbon atoms, or an amino group having an aryl group having 6 to 12 carbon atoms. A This may be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a phenoxy group, a heteroaryl group having 5 to 12 carbon atoms, or an amino group having a substituted or unsubstituted phenyl group.

[0038] Specifically, R AThis may be a methyl group, a trifluoromethyl group, an iso-propyl group, a tert-butyl group, a C(C2H5)2 group, a cyclohexyl group, a phenyl group, a phenyl group having a deuterium atom, a phenyl group having 1 to 3 methyl groups, a phenyl group having 1 to 2 iso-propyl groups, a phenyl group having a tert-butyl group, a phenyl group having a cyano group, a ter-phenyl group, a fluorenyl group, a naphthyl group, a phenoxy group, a thiophenoxy group, a carbazolyl group, a phenoxazine group, an acridine group having a methyl group, a pyridyl group, a thiophenyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a triazine having 1 to 2 phenyl groups, an amino group having a phenyl group, an amino group having a phenyl group having a methyl group, an amino group having an ethyl group, or a triphenylsilyl group. A This may be a methyl group, a phenyl group, a phenyl group having 1 to 3 methyl groups, a fluorenyl group, an amino group having a phenyl group, a pyridyl group, or a phenoxy group.

[0039] Furthermore, the skeleton represented by general formula G1 preferably has 2 to 6 nitrogen atoms in the entire skeleton. Having 2 to 6 nitrogen atoms improves the stability of the molecule. Specifically, in general formula G1, A 11 Or A 15 One of them is a nitrogen atom, and the others are CR A And A 21 Or A 25 One of them is a nitrogen atom, and the others are CR A It is fine if A 11 Or A 15 and A 21 Or A 25 CR A That's fine.

[0040] <X 1 and X 2 > In general formula G1, X 1 and X 2 These are oxygen atoms, sulfur atoms, tellurium atoms, selenium atoms, and NR B Each is independently selected from the group consisting of R.B Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups.

[0041] X 1 and X 2 These may be the same or different, but from the viewpoint of ease of synthesis, it is preferable that they be the same.

[0042] R B When there are multiple R B They may be the same or different. From the viewpoint of ease of synthesis, R B When there are multiple R B It is preferable that they are the same.

[0043] R BThis may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted thioalkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted thioaryl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted thioheteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, or a nitro group.

[0044] X 1 and X 2 It consists of oxygen atoms, sulfur atoms, and NR B It is preferable to select each independently from the group consisting of R. B This may be an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a phenyl group substituted with a deuterium atom, and is preferably a phenyl group.

[0045] <Other> In general formula G1, adjacent R A Allies, R B and substituents on ring C, or adjacent R A and R B They may combine to form a ring. For example, A 11 Or A 15 , and, A 21 Or A 25 R A It has X 1 and X 2 R B When A 11 and A 12 R possessed A Fellow, A 12 and A13 The R possessed by A each other, A 13 and A 14 The R possessed by A each other, A 14 and A 15 The R possessed by A each other, A 15 The R possessed by A and X 2 The R possessed by B , the substituent possessed by ring C and X 2 The R possessed by B , A 21 and A 22 The R possessed by A each other, A 22 and A 23 The R possessed by A each other, A 23 and A 24 The R possessed by A each other, A 24 and A 25 The R possessed by A each other, A 25 The R possessed by A and X 1 The R possessed by B , the substituent possessed by ring C and X 1 The R possessed by B At least one of them may combine to form a ring.

[0046] Also, A 11 to A 15 , and, A 21 to A 25 possess R A , X 1 and X 2 ​​​​​​​​​​​​​​​​​​​​​​​​​​​​​15 R possessed A Fellow, A 15 R possessed A and X 2 R possessed B , A 21 and A 22 R possessed A Fellow, A 22 and A 23 R possessed A Fellow, A 23 and A 24 R possessed A Fellow, A 24 and A 25 R possessed A Fellow, or A 25 R possessed A and X 1 R possessed B At least one of them may be joined to form a ring.

[0047] Also, A 11 Or A 15 , and, A 21 Or A 25 R A When there is an adjacent R A They may join together to form a ring. Specifically, A 11 and A 12 R possessed A Fellow, A 12 and A 13 R possessed A Fellow, A 13 and A 14 R possessed A Fellow, A 14 and A 15 R possessed A Fellow, A 21 and A 22 R possessed A Fellow, A 22 and A 23 R possessed A Fellow, A 23 and A 24 R possessed A Fellow, A 24 and A 25 R possessed A At least one of them may be joined together to form a ring.

[0048] Furthermore, in general formula G1, adjacent R A Allies, R B and substituents on ring C, or adjacent R A and R B However, when they bond to form a ring, the ring may be a 5-membered ring or a 6-membered ring. The ring may also be an aromatic hydrocarbon ring or a heteroaromatic ring, an aromatic hydrocarbon ring having 6 to 14 carbon atoms or a heteroaromatic ring having 5 to 16 carbon atoms, an aromatic hydrocarbon ring having 6 to 10 carbon atoms or a heteroaromatic ring having 5 to 12 carbon atoms, an aromatic hydrocarbon ring having 6 to 10 carbon atoms or a heteroaromatic ring having 5 to 8 carbon atoms. Specifically, it may be benzene, naphthalene, anthracene, phenanthrene, furan, benzofuran, dibenzofuran, thiophene, benzothiophene, or dibenzothiophene, or benzene, naphthalene, furan, benzofuran, thiophene, or benzothiophene, or benzene, naphthalene, benzofuran, or benzothiophene.

[0049] The organic compound according to this embodiment is preferably an organic compound represented by general formula G2 or G3, and more preferably an organic compound represented by general formula G2.

[0050] [ka]

[0051] 31 , A 32 , A 41 , A 42 > In general formulas G2 and G3, A 31 , A 32 , A 41 , and A 42 CR C R is independently selected from the group consisting of nitrogen atoms. A ​Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. C When there are multiple R C They may be the same or different.

[0052] R C This may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted thioalkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted thioaryl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted thioheteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, or a nitro group. C Each of these may be independently selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group having 1 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 5 carbon atoms. Or, R CEach of these may be independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, and a substituted or unsubstituted triazine ring. Or, R C Each of these may be independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted pyridyl group.

[0053] Specifically, R C Each of these may be independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, a C(C3H7)2, a phenyl group, a phenyl group having an alkyl group with 1 to 4 carbon atoms, a pyridyl group, a triazine ring, and a triazine ring having a phenyl group. C Each of these may be independently selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, a phenyl group, a phenyl group having an alkyl group with 1 to 4 carbon atoms, and a triazine ring. C R may be a hydrogen atom, a methyl group, or a pyridyl group. C This may be a hydrogen atom or a methyl group.

[0054] Also, adjacent R C R that are the same or adjacent to each other B and R C They may combine to form a ring. For example, X 1 and X 2 R B It has A 31 and A 32 R C When X 1 R possessed B and A 32 R possessed C , or X 2 R possessed B and A 32 R possessed C They may combine to form a ring. Also, for example, X 1 and X2 R B It has A 31 , A 32 , A 41 , and A 42 R C When X 1 R possessed B and A 32 R possessed C , A 32 R possessed C and A 42 R possessed C , A 42 R possessed C and X 2 R possessed B , A 31 R possessed C and A 41 R possessed C At least one of them may be joined together to form a ring.

[0055] Also, adjacent R C R that are the same or adjacent to each other B and R C They do not bond to form a ring, but adjacent R A They may join together to form a ring.

[0056] Furthermore, the organic compounds according to the present invention are preferably represented by general formulas G4-1 to G4-10 and G5-1 to G5-12.

[0057] [ka]

[0058] [ka]

[0059] <R 11 ~R 15 , R 21 ~R 25 , R 31 , R 32 , R 111 ~R116 , R 211 ~R 216 > In general formulas G5-1 to G-12, R 11 ~R 15 , R 21 ~R 25 , R 31 , R 32 , R 111 ~R 116 , R 211 ~R 216 Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups.

[0060] R 11 ~R 15 , R 21 ~R 25 , R 31 , R 32 , R 111 ~R 116 , R 211 ~R 216 Each of these may be independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 10 carbon atoms. Or, R 11 ~R 15 , R 21 ~R 25 , R 31 , R 32 , R 111 ~R 116 , R 211 ~R 216Each of these may be independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. Or, R 111 ~R 117 , R 211 ~R 217 may be a hydrogen atom or a deuterium atom. Or, R 111 ~R 117 , R 211 ~R 217 It may be a hydrogen atom.

[0061] R 11 ~R 15 , R 21 ~R 25 , R 31 , R 32 , R 111 ~R 116 , R 211 ~R 216 , R B Adjacent elements may or may not join to form a ring. The ring may be a five-membered ring or a six-membered ring, or it may be a six-membered ring. 11 ~R 15 , R 21 ~R 25 , R 31 , R 32 , R 111 ~R 116 , R 211 ~R 216 , R B When adjacent elements join together to form a ring, R 15 and X 1 R possessed B , R 25 and X 1 R possessed B They may combine to form a ring.

[0062] <X 3 and X 4 > X 3 and X 4 These are oxygen atoms, sulfur atoms, tellurium atoms, selenium atoms, C=O, and NR DEach is independently selected from the group consisting of . Also, X 3 and X 4 R may be an oxygen atom, a sulfur atom, or C=O. D Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups.

[0063] R D R may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. D This may be a hydrogen atom, a deuterium atom, an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted phenyl group.

[0064] X 3 and X 4 These may be the same or different, but from the viewpoint of ease of synthesis, it is preferable that they be the same.

[0065] R D When there are multiple R D They may be the same or different. From the viewpoint of ease of synthesis, R D When there are multiple R D It is preferable that they are the same.

[0066] <Other> In the organic compounds according to this embodiment, the organic compounds represented by general formulas G4-1 to G4-10 are preferably organic compounds represented by general formulas G4-1 to G4-5, and more preferably organic compounds represented by general formula G4-1. Organic compounds represented by general formulas G4-1 to G4-5 are preferred because they tend to exhibit a small full width at half maximum of the emission peak in the emission spectrum, and are therefore expected to have particularly excellent color purity. Among these, the organic compound represented by general formula G4-1 is particularly preferred because it is easy to synthesize.

[0067] Furthermore, in the organic compounds according to this embodiment, the organic compounds represented by general formulas G5-1 to G5-15 are preferably organic compounds represented by general formulas G5-1 to G5-12, and more preferably organic compounds represented by general formulas G5-1 to G5-8. Since the organic compounds represented by general formulas G5-1 to G5-12 are skeletons that exhibit high oscillator strength, when the organic compounds according to this embodiment are used in an organic light-emitting device, high luminescence efficiency can be expected to be obtained. In addition, the organic compounds represented by general formulas G5-1 to G5-8 are preferred because they tend to have particularly small molecular weights and excellent sublimation properties compared to the organic compounds represented by general formulas G5-9 to G5-12.

[0068] The characteristics of the organic compound according to this embodiment will be described below.

[0069] The organic compounds according to this embodiment have a transition dipole moment oriented along the long axis of the molecule, and their conjugate length is more elongated compared to the comparative organic compounds C1 and C2. The oscillator strength tends to be high when the direction in which the conjugate length is elongated and the direction of the transition dipole moment are roughly coincide. Therefore, the organic compounds according to this embodiment are organic compounds that exhibit high oscillator strength.

[0070] Here, we will explain the relationship between oscillator strength and quantum yield (luminescence efficiency). As described in paragraph

[0262] of JP 2020-47930 and paragraph

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

[0071] Therefore, when the organic compound according to this embodiment is used in an organic light-emitting device, it is expected that high luminescence efficiency can be obtained.

[0072] Figures 9 and 10 show the orbital distribution of the HOMO and LUMO, and the direction and magnitude of the transition dipole moment, for the organic compound according to this embodiment and for the organic compound in the comparative example. According to Figures 9 and 10, in the organic compound according to this embodiment, the HOMO is distributed throughout the entire general formula G1, and the direction of the transition dipole moment is along the long axis of the molecule. Therefore, the transition dipole moment shows a large value. Specifically, the HOMO is A of the general formula G1. 13 , A 14 , A 23 , and A 24 The orbitals are sufficiently distributed throughout the entire skeleton. On the other hand, among the organic compounds in the comparative example, compound C1 had a small transition dipole moment because the HOMO orbitals were not distributed throughout the entire skeleton. Also, compound C2 had a small transition dipole moment because the direction of the transition dipole moment was along the short axis of the molecule. Compounds with larger transition dipole moments exhibit higher oscillator strengths; therefore, the organic compounds according to this embodiment exhibit high oscillator strengths.

[0073] The HOMO and LUMO orbital distributions, as well as the transition dipole moment, were plotted using Gaussian 16 (Gaussian 16, Revision C.01, MJ Frisch, et al, Gaussian, Inc., Wallingford CT, 2019), molecular orbital calculation software from Gaussian, Inc., USA.

[0074] Furthermore, if the organic compound according to this embodiment has a fused ring structure, it is preferable that the fused ring structure is in the direction of the transition dipole moment. In the organic compound according to this embodiment, the direction of the transition dipole moment coincides with the direction of the long axis of general formula G1, so the transition dipole moment exhibits a higher value. Therefore, if general formula G1 further has a fused ring structure, it is preferable that the fused ring structure is in the direction of the long axis of general formula G1. Specifically, it is preferable that the organic compound is represented by general formulas G5-3 to G5-5, and more preferably that it is represented by general formulas G5-3 and G5-4.

[0075] Among the organic compounds according to this embodiment, the synthesis route for E14 is, for example, the following synthesis route, but is not limited thereto.

[0076] [ka]

[0077] The following are specific examples of organic compounds according to this embodiment. However, the present invention is not limited to the following compounds.

[0078] [ka]

[0079] [ka]

[0080] [ka]

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] (2) Organic light-emitting element Next, an organic light-emitting element according to one embodiment of the present invention will be described. The organic light-emitting element 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 element 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 a light-emitting layer. The organic compound according to the present invention may be contained in the organic compound layer, and preferably it is contained in the light-emitting layer. Here, if the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have a hole injection layer, a hole transport layer, an electron blocking layer, a hole-exciton blocking layer, an electron transport layer, an electron injection layer, etc., in addition to the light-emitting layer. The light-emitting layer may be a single layer or a laminate consisting of multiple layers. If there are multiple light-emitting layers, a charge generation layer may be provided between the light-emitting layers. The charge generation layer may be composed of a compound whose LUMO (Lowest Unoccupied Molecular Orbital) energy level is lower than that of the hole transport layer, and the LUMO energy level of the charge generation layer may be lower than that of the HOMO energy level of the hole transport layer. Here, the HOMO and LUMO energy levels of the organic compound layer may be those of the organic compound with the largest weight ratio in the organic compound layer.

[0085] In an organic light-emitting element according to one embodiment of the present invention, if the organic compound according to the present invention is included in the light-emitting layer, the light-emitting layer may consist only of the organic compound according to the present invention, or it may consist of the organic compound according to the present invention and other compounds. Here, if the light-emitting layer consists 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 for the light-emitting layer, or as a guest material. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host material is also called the "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 called the "guest," "dopant material," "dopant," or "third compound," and is a compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and is the compound that is primarily responsible for light emission. For this reason, the guest material is sometimes also called the light-emitting material. The assist material is also called the "assist" or "second compound," and is a compound with a smaller mass ratio than the host material among the compounds constituting the light-emitting layer, and assists the light emission of the guest material. The assist material is also called the second host.

[0086] Here, let S1(H) be the lowest singlet excitation energy of the host material, S1(D) be the lowest singlet excitation energy of the guest material, and S1(A) be the lowest singlet excitation energy of the assist material. The guest material may be considered to be an organic compound according to the present invention. In this case, it is preferable that the organic light-emitting device according to this embodiment satisfies S1(H)>S1(D) or S1(H)>S1(A)>S1(D). By satisfying the above relationship between the lowest singlet excitation energy of the compound included in the organic light-emitting device according to this embodiment, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting device with superior luminescence efficiency.

[0087] When the organic compound according to the present invention is used as a guest material for the light-emitting layer, the concentration of the guest material may be 0.01% by mass or more and less than 50% by mass relative to the entire light-emitting layer, preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.01% by mass or more and 5% by mass or less. When the light-emitting layer has an assist material, the assist material may be 1% by mass or more and less than 50% by mass relative to the entire light-emitting layer, preferably 10% by mass or more and less than 50% by mass.

[0088] This light-emitting layer may be a single layer or multiple layers, and by including light-emitting materials having other light-emitting colors, it is possible to mix the light emission with the blue light emission of this embodiment. Multiple layers mean a state in which one light-emitting layer and another light-emitting layer are stacked on top of each other. In this case, the light-emitting color of the organic light-emitting element is not limited to blue. More specifically, it may be white or an intermediate color. In the case of white, the other light-emitting layer emits a color other than blue, i.e., red or green. Furthermore, the film is formed by vapor deposition or coating.

[0089] The organic compound according to the present invention can be used as a constituent material for organic compound layers other than the light-emitting layer constituting the organic light-emitting device according to this embodiment. Specifically, it may be used as a constituent material for electron transport layers, electron injection layers, hole transport layers, hole injection layers, hole blocking layers, etc. In this case, the light-emitting color of the organic light-emitting device is not limited to blue. More specifically, it may be white light or an intermediate color.

[0090] (3) Other compounds In addition to the organic compounds according to the present invention, conventionally known low-molecular-weight and high-molecular-weight hole-implanting or hole-transporting compounds, host materials, luminescent compounds, electron-injecting or electron-transporting compounds, etc., can be used together as needed. Examples of these compounds are listed below.

[0091] As hole-injection transport materials, materials with high hole mobility are preferred to facilitate hole injection from the anode and to transport the injected holes to the light-emitting layer. Furthermore, materials with a high glass transition temperature are preferred to suppress crystallization of organic compounds in the organic light-emitting element. Examples of low-molecular-weight and high-molecular-weight materials with hole-injection transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. In addition, the above-mentioned hole-injection transport materials are also suitably used in electron-blocking layers. Moreover, when the hole-injection layer is fabricated by a coating method, a mixture of polyethylenedioxythiophene and polystyrene sulfonic acid (PEDOT:PSS), which is commonly used as a hole-injection material, may be used. Specific examples of compounds used as hole-injection transport materials are shown below, but are not limited to these.

[0092] [ka]

[0093] Among the hole-injection transportable materials listed, HT16 to HT18 can reduce the driving voltage when used in the layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2 to HT7, HT10, HT12, and HT22 to 28 may be used in the organic compound layer adjacent to HT16. Hole-transportable polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives may also be used. In addition, inorganic insulating layers such as SiO2 and SiN, or organosilicon polymers such as siloxanes can also be used. Furthermore, multiple materials may be used in a single organic compound layer.

[0094] Guest materials primarily involved in luminescence include donor-acceptor type organic compounds, boron-containing complexes, indolocarbazole 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-quinolinolate)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Furthermore, when creating a luminescent layer by coating, polymer compounds with luminescence properties are mainly used. This is because polymer compounds tend to exhibit high glass transition temperatures, making them less prone to crystallization compared to low-molecular-weight systems. Specific examples of materials used include polymer compounds such as polyphenylene vinylene (PPV), polyfluorene (PF), polyvinylcarbazole (PVK), and their derivatives.

[0095] The following are some specific examples of compounds used as luminescent materials, but of course, they are not the only ones.

[0096] [ka]

[0097] [ka]

[0098] The following are specific examples of compounds used as host or assist materials in the light-emitting layer, but of course, they are not the only ones that can be used.

[0099] [ka]

[0100] As electron-transporting materials, any material capable of transporting electrons injected from the cathode to the light-emitting layer can be arbitrarily selected, taking into consideration the balance with the hole mobility of the hole-transporting material. Examples of materials with electron-transporting properties include oxadiazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron-transporting materials are also suitably used in the hole-blocking layer.

[0101] The following are specific examples of compounds used as electron transport materials, but of course, they are not the only ones.

[0102] [ka]

[0103] Electron-injectable materials can be arbitrarily selected from those that allow for easy electron injection from the cathode, taking into consideration the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. Examples include alkali metal compounds such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fluvalene derivatives, and acridine derivatives.

[0104] It can also be used in combination with the electron transport materials mentioned above.

[0105] Furthermore, the organic compounds according to the present invention can also be used as ink compositions.

[0106] The ink composition according to this embodiment contains at least one compound represented by general formula G1. By using the ink composition according to this embodiment, it becomes possible to fabricate a layer made of organic compounds constituting an organic light-emitting element, particularly a light-emitting layer, by a coating method, making it possible to easily produce large-area elements at relatively low cost. Examples of solvents for dissolving the compound represented by general formula G1 include toluene, xylene, mesitylene, dioxane, methylnaphthalene, tetrahydrofuran, diglyme, 1,2-dichlorobenzene, and 1,2-dichloropropane. These solvents can be used alone or in combination of two or more. Among these, it is preferable to use a solvent with a moderate evaporation rate, specifically one with a boiling point of about 70 to 200°C, as it is easier to obtain a thin film with a uniform thickness. The ink composition according to this embodiment may also contain other additive compounds. Examples of additive compounds include the above-mentioned known light-emitting layer host or light-emitting assist material, hole transport material, light-emitting material, electron transport material, etc.

[0107] In the ink composition according to this embodiment, the concentration of the compound represented by general formula G1 is preferably 0.05% by weight or more and 20% by weight or less, and more preferably 0.1% by weight or more and 5% by weight or less, relative to the entire composition.

[0108] The ink composition according to this embodiment can be formed into a film by methods such as spin coating, bar coating, slit coating, inkjet, nozzle coating, casting, or gravure printing to create the organic light-emitting element described later.

[0109] (4) Configuration of organic light-emitting element The following describes the components that make up the organic light-emitting element of this embodiment.

[0110] An organic light-emitting element is provided on a substrate by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode. A protective layer, a color filter, a microlens, etc., may be provided on the second electrode. If a color filter is provided, a planarization layer may be provided between it and the protective layer. The planarization layer can be made of acrylic resin or the like. The same applies when a planarization layer is provided between the color filter and the microlens.

[0111] [substrate] Examples of substrates include quartz, glass, silicon wafers, resins, and metals. The substrate may also be equipped with switching elements such as transistors and wiring, and an insulating layer may be provided on top of them. The insulating layer can be made of any material that allows for the formation of contact holes between it and the first electrode, while ensuring insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, and silicon nitride can be used.

[0112] [electrode] A pair of electrodes can be used. This pair consists of 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 the higher potential is the anode, and the other is the cathode. Alternatively, the electrode that supplies holes to the light-emitting layer can be the anode, and the electrode that supplies electrons can be the cathode.

[0113] The anode material should ideally have a high work function. For example, elemental metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, or mixtures containing these, or alloys combining them, as well as metal oxides such as tin oxide, zinc oxide, indium oxide, tin-indium oxide (ITO), and zinc-indium oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0114] These electrode materials may be used individually or in combination of two or more types. Furthermore, the anode may consist of a single layer or multiple layers.

[0115] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys thereof, laminated materials, etc. can be used. The above materials can also function as a reflective film without having the role of an electrode. When used as a transparent electrode, an oxide transparent conductive layer such as indium tin oxide (ITO), indium zinc oxide, etc. can be used, but it is not limited thereto. For the formation of the electrode, photolithography technology can be used.

[0116] As the constituent material of the cathode, those with a small work function are preferable. For example, alkali metals such as lithium, alkaline earth metals such as calcium, metals such as aluminum, titanium, manganese, silver, lead, chromium, etc. alone or mixtures containing these can be mentioned. Alternatively, alloys combining these metal elements can also be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver, etc. can be used. The use of metal oxides such as indium tin oxide (ITO) is also possible. These electrode materials can be used alone or in combination of two or more. Also, the cathode may have a single-layer structure or a multi-layer structure. Among them, it is preferable to use silver, and in order to reduce the aggregation of silver, it is more preferable to use a silver alloy. As long as the aggregation of silver can be reduced, the ratio of the alloy is not limited. For example, silver: other metals may be 1:1, 3:1, etc.

[0117] 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. As the formation method of the cathode, although not particularly limited, the use of direct current and alternating current sputtering methods, etc. is more preferable because the film coverage is good and the resistance is easily reduced.

[0118] [Organic Compound Layer] The organic compound layer may be formed as a single layer or as multiple layers. If there are multiple layers, they may be called a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on their function. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms and inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be placed between the first electrode and the second electrode, or it may be placed in contact with the first electrode and the second electrode.

[0119] The organic compound layers constituting the organic light-emitting element according to this embodiment (hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) are formed by the method shown below.

[0120] The organic compound layer constituting the organic light-emitting element according to this embodiment can be formed using dry processes such as vacuum deposition, ionization deposition, sputtering, or plasma deposition. Alternatively, a wet process can be used instead of a dry process, in which the organic compound is dissolved in a suitable solvent and the layer is formed by a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0121] By forming layers using methods such as vacuum deposition or solution coating, crystallization is less likely to occur, resulting in excellent stability over time. Furthermore, when forming films using coating methods, it is possible to combine the film with an appropriate binder resin.

[0122] Examples of the binder resins mentioned above include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0123] Furthermore, these binder resins may be used individually as homopolymers or copolymers, or as a mixture of two or more types. Additionally, known additives such as plasticizers, antioxidants, and UV absorbers may be used in combination as needed.

[0124] [Protective layer] A protective layer may be provided on the cathode. For example, by bonding glass with a desiccant to the cathode, the intrusion of water and other substances into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water and other substances into the organic compound layer. For example, after forming the cathode, it may be transported to another chamber without breaking the vacuum and a silicon nitride film with a thickness of 2 μm may be formed by the CVD method to serve as a protective layer. A protective layer may also be provided using atomic deposition (ALD) after film formation by the CVD method. The material of the film formed by the ALD method is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed on the film formed by the ALD method by the CVD method. The film formed by the ALD method may have a smaller film thickness than the film formed by the CVD method. Specifically, the film thickness of the film formed by the ALD method may be 50% or less, or even 10% or less, of the film thickness of the film formed by the CVD method.

[0125] [Color Filter] A color filter may be provided on top of the protective layer. For example, a color filter that takes into account the size of the organic light-emitting element may be provided on a separate substrate and bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer as described above using photolithography technology. The color filter may be made of polymer.

[0126] [Planarization layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer is provided to reduce the unevenness of the layer below. It may also be called a material resin layer without limiting its purpose. The planarizing layer may be composed of an organic compound, which may be low molecular weight or high molecular weight, but high molecular weight is preferred.

[0127] The planarization layer may be provided above or below the color filter, and its constituent materials may be the same or different. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, urea resin, etc.

[0128] [Microlens] The organic light-emitting element according to this embodiment may have an optical element 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. If it has a hemispherical shape, among the tangents that are tangent to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between that tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be similarly determined in any cross-sectional view. That is, among the tangents that are tangent 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 that tangent and the semicircle is the vertex of the microlens.

[0129] Furthermore, the midpoint of a microlens can also be defined. In the cross-section of a microlens, a line segment can be imagined from the point where one arc shape begins to the point where another arc shape begins, and the midpoint of this line segment can be called the midpoint of the microlens. The cross-section used to determine the vertices and midpoints may be a cross-section perpendicular to the insulating layer.

[0130] [Opposite substrate] A counter substrate may be provided on the planarized layer. The counter substrate is called a counter substrate because it is provided in a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. The counter substrate may be the second substrate if the aforementioned substrate is referred to as the first substrate.

[0131] [Pixel circuit] The light-emitting device may have a pixel circuit connected to a light-emitting element. The pixel circuit may be an active matrix type that independently controls light emission of a first light-emitting element and a second light-emitting element. The active matrix type circuit may be voltage programming or current programming. The driving circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the light emission luminance of the light-emitting element, a transistor that controls the light emission timing, a capacitor that holds the gate voltage of the transistor that controls the light emission luminance, and a transistor for connecting to GND without passing through the light-emitting element.

[0132] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of the transistor constituting the pixel circuit may be smaller than the mobility of the transistor constituting the display control circuit.

[0133] The slope of the current-voltage characteristics of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistor constituting the display control circuit. The slope of the current-voltage characteristics can be measured by so-called Vg-Ig characteristics.

[0134] The transistor constituting the pixel circuit is a transistor connected to a light-emitting element such as a first light-emitting element.

[0135] [Pixel] The organic light-emitting device has a plurality of pixels. The pixels have sub-pixels that emit different colors from each other. The sub-pixels may have light emission colors of RGB, for example.

[0136] In the pixel, a region also called a pixel aperture emits light. This region is the same as the first region. The pixel aperture may be 15 μm or less and may be 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc.

[0137] The distance between sub-pixels may be 10 μm or less, and specifically, may be 8 μm, 7.4 μm, 6.4 μm.

[0138] Pixels can take on known arrangements in a plan view. For example, they may be in a stripe arrangement, delta arrangement, pentile arrangement, or Bayer arrangement. The shape of subpixels in a plan view may be any known shape. For example, rectangles, rhombuses, hexagons, etc. Of course, even if it is not a precise shape, if it is close to a rectangle, it is included in the category of rectangles. The shape of subpixels and the pixel arrangement can be used in combination.

[0139] (5) Applications of the organic light-emitting element according to this embodiment The organic light-emitting element according to this embodiment can be used as a component of image display devices, display devices, lighting devices, and the like. Other applications include exposure light sources for electrophotographic image forming apparatuses, backlights for liquid crystal display devices, and light-emitting devices with a color filter in a white light source.

[0140] The display device may also be an image information processing device that has an image input unit for receiving image information from an area CCD, linear CCD, memory card, etc., an information processing unit for processing the input information, and displays the input image on the display unit.

[0141] Furthermore, the display unit of the imaging device or inkjet printer may have a touch panel function. The driving method for this touch panel function may be infrared, capacitive, resistive, or electromagnetic induction, and is not particularly limited. The display device may also be used as the display unit of a multifunction printer.

[0142] Next, the display device according to this embodiment will be described with reference to the drawings.

[0143] Figure 1 is a schematic cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to this organic light-emitting element. The transistor is an example of an active element. The transistor may also be a thin-film transistor (TFT).

[0144] Figure 1(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The light emission color may be distinguished by the wavelength emitted from the light-emitting layer, or the light emitted from the sub-pixel may be selectively transmitted or color-converted by a color filter or the like. Each sub-pixel has a reflective electrode 2 which is a first electrode, an insulating layer 3 covering the end of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, a transparent electrode 5, a protective layer 6, and a color filter 7 on an interlayer insulating layer 1.

[0145] The interlayer insulating layer 1 may have transistors and capacitive elements placed in the layer below or inside it. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0146] The insulating layer 3 is also called the bank or pixel isolation layer. It covers the edge of the first electrode and surrounds the first electrode. The portion without the insulating layer is in contact with the organic compound layer 4 and becomes the light-emitting region.

[0147] 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.

[0148] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0149] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is shown as a single layer, it may consist of multiple layers. Each layer may contain an inorganic compound layer and an organic compound layer.

[0150] The color filters 7 are classified into 7R, 7G, and 7B according to their color. The color filters may be formed on a planarization film (not shown). The color filters may also have a resin protective layer (not shown). Alternatively, the color filters may be formed on a protective layer 6, or they may be bonded together after being placed on an opposing substrate such as a glass substrate.

[0151] The display device 100 in Figure 1(b) shows an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided, with an insulating layer 12 on top of it. An active element 18 such as a TFT is placed on the insulating layer, and the gate electrode 13, gate insulating film 14, and semiconductor layer 15 of the active element are arranged therein. The active element 18 is also composed of a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on top of the active element 18. The anode 21 and the source electrode 17 that constitute the organic light-emitting element 26 are connected via a contact hole 20 provided in the insulating film.

[0152] Note that the method of electrical connection between the electrodes (anode, cathode) included in the organic light-emitting element 26 and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the configuration shown in Figure 1(b). In other words, it is sufficient if either the anode or cathode is electrically connected to either the source electrode or the drain electrode of the TFT. TFT refers to a thin-film transistor.

[0153] In the display device 100 shown in Figure 1(b), the organic compound layer is depicted as a single layer, but the organic compound layer 22 may consist of multiple layers. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce the degradation of the organic light-emitting element.

[0154] In the display device 100 shown in Figure 1(b), a transistor is used as the switching element, but other switching elements may be used instead.

[0155] Furthermore, the transistor used in the display device 100 in Figure 1(b) is not limited to a transistor using a single-crystal silicon wafer, but may also be a thin-film transistor having an active layer on an insulating surface of the substrate. Examples of active layers include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0156] The transistors included in the display device 100 in Figure 1(b) may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the transistors are manufactured by processing the substrate itself, such as a Si substrate. In other words, having transistors within a substrate can be seen as the substrate and transistors being formed as a single unit.

[0157] The organic light-emitting element according to this embodiment has its luminescence controlled by a TFT, which is an example of a switching element, and by providing multiple organic light-emitting elements on the surface, an image can be displayed using the luminescence of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor made of low-temperature polysilicon, or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "within the substrate." Whether to provide a transistor within the substrate or to use a TFT is selected depending on the size of the display area; for example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0158] Figure 2 is a schematic diagram showing an example of a display device according to this embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The display panel 1005 may have 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 does not need to be provided if the display device is not a portable device, or it may be provided in a different location even if it is a portable device.

[0159] The display device according to this embodiment may have a color filter having red, green, and blue colors. The color filter may have the red, green, and blue colors arranged in a delta array.

[0160] The display device according to this embodiment may be used in the display unit of a mobile terminal. In that case, it may have both display and operation functions. Examples of mobile terminals include smartphones and other mobile phones, tablets, and head-mounted displays.

[0161] The display device according to this embodiment may be used in the display unit of an imaging device having an image sensor that receives light. The imaging device may have a display unit that displays information acquired by the image sensor. The display unit may be an external display unit or a display unit located inside the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0162] Figure 3(a) is a schematic diagram showing an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operating unit 1103, and a housing 1104. The viewfinder 1101 and the rear display 1102 may have organic light-emitting elements according to this embodiment. In that case, the viewfinder 1101 and the rear display 1102 may display not only the image to be captured, but also environmental information, imaging instructions, etc. Environmental information may include the intensity of ambient light, the direction of ambient light, the speed at which the subject is moving, the possibility of the subject being obscured by an obstacle, etc.

[0163] Since the optimal timing for imaging is very short, it is best to display the information as quickly as possible. Therefore, it is preferable to use a display device using the organic light-emitting element according to this embodiment, because organic light-emitting elements have a fast response speed.

[0164] The imaging device 1100 may further include an optical section (not shown). The lenses in the optical section may be one or more, and they form an image on the image sensor housed in the housing 1104. The focus can be adjusted by adjusting the relative positions of the multiple lenses. This operation can also be performed automatically. The imaging device may also be called a photoelectric converter. The photoelectric converter may not capture images sequentially, but may include methods of capturing images such as detecting the difference from the previous image or extracting from an image that is always being recorded.

[0165] Figure 3(b) is a schematic diagram showing an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type response unit. The operation unit may also be a biometric recognition unit that recognizes fingerprints to unlock or otherwise perform actions. An electronic device having a communication unit can also be called a communication device. The electronic device may further have a camera function by including a lens and an image sensor. Images captured by the camera function are displayed on the display unit. Examples of electronic devices include smartphones and laptop computers.

[0166] Figure 4 is a schematic diagram showing an example of a display device according to this embodiment. Figure 4(a) is a display device such as a television monitor or a PC monitor. The display device 1300 has a housing 1301 and a display unit 1302. An organic light-emitting element according to this embodiment may be used in the display unit 1302.

[0167] The display device 1300 may have a housing 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in Figure 4(a). The lower edge of the housing 1301 may also serve as the base.

[0168] Furthermore, the housing 1301 and the display unit 1302 may be curved. Their radius of curvature may be between 5000 mm and 6000 mm.

[0169] Figure 4(b) is a schematic diagram showing another example of the display device according to this embodiment. The display device 1310 in Figure 4(b) is configured to be foldable and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have organic light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single display device without seams. The first display unit 1311 and the second display unit 1312 can be separated by a bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may together display a single image.

[0170] Figure 5(a) is a schematic diagram showing an example of a lighting device according to this embodiment. The lighting device 1400 may have a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may have an organic light-emitting element according to this embodiment. The lighting device 1400 may have an optical film 1404 to improve the color rendering of the light source. The lighting device 1400 may also have a light diffusion section 1405 to effectively diffuse the light from the light source. The lighting device 1400 having a light diffusion section 1405 allows light to be delivered over a wide area. The optical film 1404 and the light diffusion section 1405 may be provided on the light-emitting side of the lighting. A cover may be provided on the outermost part as needed.

[0171] The lighting device is, for example, a device for illuminating a room. The lighting device may emit white light, daylight white light, or any other color from blue to red. The lighting device according to this embodiment may have a dimming circuit for adjusting the brightness of these colors. The lighting device according to this embodiment may also have a power supply circuit 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. White light has a color temperature of 4200K, and daylight white light has a color temperature of 5000K. The lighting device according to this embodiment may further have a color filter.

[0172] Furthermore, the lighting device according to this embodiment may have a heat dissipation section. The heat dissipation section releases heat from inside the device to the outside, and examples include metals, ceramics, and the like with high thermal conductivity.

[0173] Figure 5(b) is a schematic diagram of an automobile, which is an example of a mobile body according to this embodiment. The automobile has a taillight, which is an example of a lighting device. The automobile 1500 has a taillight 1501 and a body 1503, and the taillight may illuminate when the brakes are applied or the like. The body 1503 may also be called the machine body. The automobile 1500 may have a window 1502 attached to the body 1503.

[0174] The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp may have a protective member to protect the light source. The protective member has a reasonably high strength and can be made of any transparent material, but it is preferably made of polycarbonate or the like. A frangic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.

[0175] Window 1502 may be a transparent display if it is not a window for checking the front and rear of the vehicle. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials such as electrodes of the organic light-emitting element according to the present invention are made of transparent material.

[0176] Furthermore, as shown in Figure 5(c), the automobile 1500 includes a steering wheel 1504 for controlling the direction of movement of the moving body, a display unit 1505 mounted on the vehicle body 1503 for displaying a map, the position of the moving body, the direction of turns, etc. The display unit 1505 may have an organic light-emitting element according to this embodiment.

[0177] The mobile body according to this embodiment includes a drive force generating unit that generates a driving force mainly used for the movement of the mobile body, and one or both of a rotating body mainly used for the movement of the mobile body. The drive force generating unit may be an engine, a motor, etc. The rotating body may be a tire, a wheel, a ship's propeller, etc. Specifically, it may be a bicycle, an automobile, a train, a ship, an aircraft, a drone, etc. The mobile body may have a body and a light fixture or display unit provided on the body. The light fixture may emit light to indicate the position of the body.

[0178] Referencing Figure 6, examples of applications of the display devices of each embodiment described above will be explained. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, head-mounted displays, and smart contact lenses. A display device that can be used in a wearable device may have an imaging device capable of photoelectric conversion of visible light and a display device capable of emitting visible light.

[0179] Figure 6 is a schematic diagram showing an example of eyeglasses (smart glasses) according to this embodiment. The eyeglasses 1600 (smart glasses) will be explained using Figure 6(a). The eyeglasses 1600 has a display unit on the back side of the lens 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 SPAD may be provided on the front side of the lens 1601.

[0180] The eyeglasses 1600 further include a control device 1603. The control device 1603 functions as a power supply that provides power to the imaging device 1602 and the display unit. The control device 1603 also controls the operation of the imaging device 1602 and the display unit. The lens 1601 has an optical system formed therein for focusing light from the imaging device 1602 and the display unit.

[0181] Figure 6(b) illustrates the eyeglasses 1610 (smart glasses). The eyeglasses 1610 have a control device 1612, which is equipped 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. An optical system for projecting light emitted from the control device 1612 is formed on the lens 1611, and an image is projected onto the lens 1611. The control device 1612 functions as a power supply to provide power to the imaging device and the display device, and also controls the operation of the imaging device and the display device. The control device may have a gaze detection unit for detecting the wearer's gaze. Gaze detection may use infrared light. The infrared light-emitting unit emits infrared light towards the eyeball of the user who is gazing at the displayed image. An image of the eyeball is obtained by detecting the reflected light from the eyeball of the emitted infrared light using an imaging unit having a photodetector. By having a reduction means for reducing the light from the infrared light-emitting unit to the display unit in a planar view, the degradation of image quality is reduced.

[0182] The control device 1612 detects the user's gaze toward the displayed image from the image of the eyeball obtained by imaging with infrared light. Any known method can be applied to gaze detection using the image of the eyeball. For example, a gaze detection method based on the Purkinje image obtained by the reflection of the irradiated light from the cornea can be used.

[0183] More specifically, gaze detection processing is performed based on the pupil-corneal reflection method. Using the pupil-corneal reflection method, a gaze vector representing the orientation (rotation angle) of the eyeball is produced based on the pupil image and Purkinje image contained in the captured image of the eyeball, thereby detecting the user's gaze.

[0184] The display device according to this embodiment includes an imaging device having a light-receiving element, and may control the display image of the display device based on the user's gaze information from the imaging device.

[0185] Specifically, the display device determines a first field of view that the user is fixated on, and a second field of view other than the first field of view, based on gaze information. The first and second field of view may be determined by the display device's control unit, or they may be determined by an external control unit and received by the display device. Within the display area of ​​the display device, the display resolution of the first field of view may be controlled to be higher than that of the second field of view. In other words, the resolution of the second field of view may be lower than that of the first field of view.

[0186] Furthermore, the display area has a first field of view and a second field of view different from the first field of view, and based on gaze information, a higher priority area is determined from the first and second field of view. The first and second field of view areas may be determined by the control device of the display device, or they may be determined by an external control device and received. The resolution of the higher priority area may be controlled to be higher than the resolution of the areas other than the higher priority area. In other words, the resolution of areas with relatively lower priority may be set lower.

[0187] AI may be used to determine the first field of view and the field of view with higher priority. The AI ​​may be a model configured to estimate the angle of gaze and the distance to the target object at the end of the line of sight from the image of the eye, using the image of the eye and the direction the eye was actually looking in the image as training data. The AI ​​may be included in the display device, the imaging device, or an external device. If the external device includes the AI, it can preferably be applied to smart glasses that further include an imaging device for capturing images of the outside. The smart glasses can display the captured external information in real time.

[0188] Figure 7 is a schematic diagram of an HMD (head-mounted display) 2301 as a display device according to one embodiment of the present invention. Figure 7(a) is a schematic diagram showing a head-mounted display and an observer wearing it. The HMD 2301 is worn on the observer's head. Reference numeral 2302 indicates the observer's right eye, and reference numeral 2303 indicates the observer's left eye. Display lenses 2304 and 2305 constitute the right eye eyepiece optical system OR1, and display lenses 2306 and 2307 constitute the left eye eyepiece optical system OL1. Each eyepiece optical system is a coaxial optical system composed of multiple (two) display lenses. The observer's right eye 2302 is positioned in the exit pupil ER1 of the right eye eyepiece optical system OR1, and the observer's left eye 2303 is positioned in the exit pupil EL1 of the left eye eyepiece optical system OL1. The exit pupil ER1 is located at a distance E1 from the right eye eyepiece optical system OR1. Similarly, the exit pupil EL1 is located at a distance E1 from the left eyepiece optical system OL1. Optical films 2314 are provided on the surface of the right eyepiece optical system OR1 (the surface on the right eye 2302 side) and the surface of the left eyepiece optical system OL1 (the surface on the left eye 2303 side) for lens protection and light focusing.

[0189] Reference numerals 2308 and 2309 indicate display devices for the right eye and left eye, respectively. These display devices may be the display devices according to Embodiment 1. Figure 7(b) is a schematic diagram showing an example in which a display device according to one embodiment of the present invention is connected to an external device, and shows the appearance of the HMD2301 and the personal computer 2350 connected thereto. Each display device displays a display image (original image) corresponding to the image signal output from the personal computer 2350. In this configuration, the connection is wired, but it may also be wireless. Furthermore, the HMD2301 may be a standalone device with an image processing device built inside.

[0190] The eyepiece optical systems OR1 and OL1 guide light from the display devices 2308 and 2309 to the exit pupils ER1 and EL1, respectively, projecting an enlarged virtual image of the displayed image onto the observer's right eye 2302 and left eye 2303. This allows the observer to observe the displayed image (or virtual image) shown on the display devices 2308 and 2309 through the eyepiece optical systems OR1 and OL1.

[0191] Although not shown in the diagram, the HMD2301 may have a control device. The control device functions as a power supply that provides power to the display devices 2308 and 2309, and also controls the operation of the display devices 2308 and 2309.

[0192] Figure 8(a) is a schematic diagram showing an example of an image forming apparatus according to this embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fuser 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoreceptor 27. This exposure light source 28 may have an organic light-emitting element according to this embodiment. The developing unit 31 has toner or the like. The charging unit 30 charges the photoreceptor 27. The transfer unit 32 transfers the developed image to a storage medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fuser 35 fixes the image formed on the recording medium 34.

[0193] Figures 8(b) and 8(c) are diagrams showing the exposure light source 28, schematic diagrams showing how multiple light-emitting units 36 are arranged on a long substrate. Arrows 37 indicate the column direction in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis of rotation of the photoreceptor 27. This direction can also be called the long axis direction of the photoreceptor 27. Figure 8(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoreceptor 27. Figure 8(c) is a different configuration from Figure 8(b), in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are located at different positions in the row direction. In the first column, multiple light-emitting units 36 are arranged with intervals between them. In the second column, light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. That is, multiple light-emitting units 36 are also arranged with intervals between them in the row direction. The arrangement in Figure 8(c) can also be described as a grid pattern, a houndstooth pattern, or a checkerboard pattern.

[0194] As described above, by using the device employing the organic light-emitting element according to this embodiment, stable display with good image quality is possible even during long-term display. [Examples]

[0195] The present invention will be described below with reference to examples. However, the present invention is not limited to these examples.

[0196] [Example 1] The oscillator intensities of the organic compound according to the present invention and comparative examples compounds C1 and C2 were determined using Gaussian 16 (Gaussian 16, Revision C.01, MJ Frisch, et al, Gaussian, Inc., Wallingford CT, 2019), molecular orbital calculation software manufactured by Gaussian, Inc., USA. The results are shown in Table 1.

[0197] [Table 1]

[0198] [Table 2]

[0199] [Table 3]

[0200] Table 1 shows that the organic compound according to this embodiment exhibited higher oscillator strength compared to the organic compound in the comparative example. This is thought to be because the skeleton represented by general formula G1 has a structure in which the HOMO is distributed throughout the entire skeleton, and as a result, it exhibits a large transition dipole moment.

[0201] [Example 38 (Synthesis of Compound E14)]

[0202] [ka]

[0203] [Synthesis of intermediate E14a] 2-chlorobenzoic acid (15.66 g), resorcinol (5.5 g), and polyphosphate (PPA) (50 g) were mixed and stirred at 130°C for 12 hours. After cooling to room temperature, 150 ml of water was added, and extraction was performed with chloroform. Sodium bicarbonate aqueous solution was added, and extraction was performed with chloroform to separate the organic layer. The organic layer was removed by vacuum distillation, and the resulting residue was washed with a small amount of methanol and filtered by suction to obtain E14a as a pale yellow powder (16.27 g).

[0204] [Synthesis of intermediate E14b] Intermediate E14a (3.87 g), methylhydroxylamine hydrochloride (8.35 g), and pyridine (100 ml) were added and stirred at 125°C for 20 hours. After cooling, water was added and extraction was performed with methylene chloride. The resulting residue was subjected to silica gel column chromatography (solvent: hexane / methylene chloride = 1:1, v / v) to obtain E14b as a colorless powder (4.6 g).

[0205] [Synthesis of intermediate E14c] Intermediate E14b (4.05 g), cesium carbonate (5.93 g), and N,N-dimethylformamide (DMF) (160 mL) were added and the mixture was stirred at 100°C for 12 hours. After cooling, water was added and the mixture was filtered. The filtered material was vacuum-dried to obtain the crude product (3.32 g).

[0206] [Synthesis of Compound E14] Intermediate E14c (100 mg), diphenylacetylene (143 mg), iron acetate (19 mg), 1,2-bis(diphenylphosphin)ethane (24 mg), catechol (118 mg), and xylene (5 mL) were added. Under an argon atmosphere, 1.0 mol / L triisobutylaluminum-toluene solution (1.1 mL) was added and the mixture was stirred at 140 °C for 20 hours. After cooling, methanol was added, then methylene chloride was added, and silica gel column chromatography (solvent: methylene chloride) was performed. The organic layer was removed by reduced pressure. The resulting residue was dissolved in chloroform and purified by GPC (gel permeation chromatography) to obtain E14 as a yellow powder (8 mg). The obtained compound was identified by the following method.

[0207] MS(HPLC-IMS-QToFMS)m / z 665.2232(M+H,calcd for C 48 H 29 N2O2, 665.2229) [Example 39 and Comparative Example 3 (Evaluation of Compound E14 and Compound C1)] Compound E14 was dissolved in toluene, and the toluene solution was irradiated with excitation light at 360 nm. The emission quantum yield (PLQY) was then measured. The result showed that the PLQY of compound E14 was 0.835.

[0208] Compound C1 was dissolved in toluene, and its PLQY was measured in the same manner. As a result, the PLQY of compound C1 was 0.566.

[0209] The organic compound according to this embodiment has a structure represented by the general formula G1, and therefore its transition dipole moment coincides with the long axis of the molecule and exhibits a larger value than compound C1. As a result, the organic compound according to this embodiment is thought to have shown excellent luminescence efficiency.

[0210] For the reasons stated above, it is expected that using the organic compound according to the present invention in an organic light-emitting device will result in high luminescence efficiency.

[0211] Furthermore, the present invention can also take the following configuration.

[0212] (Composition 1) An organic compound characterized by being represented by the general formula G1.

[0213] [ka]

[0214] In general formula G1, ring C is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 5 to 50 carbon atoms.

[0215] A 11 Or A 15 , A 21 Or A 25 CR A R is independently selected from the group consisting of nitrogen atoms. A Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. AWhen there are multiple R A They may be the same or different.

[0216] X 1 and X 2 These are oxygen atoms, sulfur atoms, tellurium atoms, selenium atoms, and NR B Each is independently selected from the group consisting of R. B Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. B When there are multiple R B They may be the same or different.

[0217] Adjacent R A Allies, R B and substituents on ring C, or adjacent R A and R B They may combine to form a ring.

[0218] (Configuration 2) The organic compound according to composition 1, characterized by being represented by general formula G2 or G3.

[0219] [ka]

[0220] In general formulas G2 and G3, A 31 , A 32 , A 41 , and A 42 CR CR is independently selected from the group consisting of nitrogen atoms. C Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. C When there are multiple R C They may be the same or different.

[0221] Adjacent R C R that are the same or adjacent to each other B and R C They may combine to form a ring.

[0222] (Composition 3) An organic compound according to configuration 1 or 2, characterized by being represented by any one of the general formulas G4-1 to G4-10.

[0223] [ka]

[0224] (Composition 4) The organic compound according to configuration 3, characterized by being represented by any one of the general formulas G4-1 to G4-5.

[0225] (Composition 5) The organic compound described in configuration 3, characterized by being represented by the general formula G4-1.

[0226] (Composition 6) The organic compound according to configuration 1, characterized by being represented by any one of the general formulas G5-1 to G5-15.

[0227] [ka]

[0228] In general formulas G5-1 to G5-15, R 11 ~R 15 , R 21 ~R 25 , R 31 , R 32 , R 111 ~R 116 , R 211 ~R 216 Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups.

[0229] X 3 and X 4 These are oxygen atoms, sulfur atoms, tellurium atoms, selenium atoms, C=O, and NR D Each is independently selected from the group consisting of R. D Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. D When there are multiple RD They may be the same or different.

[0230] R 11 ~R 15 , R 21 ~R 25 , R 31 , R 32 , R 111 ~R 116 , R 211 ~R 216 , R B Adjacent elements may be joined together to form a ring.

[0231] (Composition 7) The organic compound according to composition 6, characterized by being represented by any one of the general formulas G5-1 to G5-12.

[0232] (Composition 8) The organic compound according to composition 6, characterized by being represented by any of the general formulas G5-1 to G5-8.

[0233] (Composition 9) The organic compound according to configuration 1, characterized in that ring C is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms.

[0234] (Composition 10) X 1 and X 2 It consists of oxygen atoms, sulfur atoms, and NR B Each is independently selected from the group consisting of R B The organic compound according to any one of the configurations 1 to 9, characterized in that it is an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a phenyl group substituted with a deuterium atom.

[0235] (Composition 11) X 1 and X 2 The organic compound according to any one of configurations 1 to 10, characterized in that each is independently selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom having a phenyl group.

[0236] (Composition 12) X 3 and X 4 The organic compound according to configuration 6, characterized in that each of the atoms is independently selected from the group consisting of an oxygen atom, a sulfur atom, and C=O.

[0237] (Composition 13) A 11 Or A 15 One of them is a nitrogen atom, and the others are CR A And A 21 Or A 25 One of them is a nitrogen atom, and the others are CR A An organic compound according to any one of configurations 1 to 12, characterized in that it is such.

[0238] (Composition 14) A 11 Or A 15 and A 21 Or A 25 CR A An organic compound according to any one of the configurations 1 to 13, characterized in that it is such.

[0239] (Composition 15) R A The organic compound according to any one of configurations 1 to 14, characterized by comprising a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms, a thioaryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 3 to 13 carbon atoms, a triphenylsilyl group, an amino group having an alkyl group having 1 to 4 carbon atoms, or an amino group having an aryl group having 6 to 12 carbon atoms.

[0240] (Composition 16) R AThe organic compound according to any one of configurations 1 to 15, characterized in that it is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a phenoxy group, a heteroaryl group having 5 to 12 carbon atoms, or an amino group having a substituted or unsubstituted phenyl group.

[0241] (Composition 17) The first electrode and the second electrode, An organic light-emitting element having an organic compound layer disposed between the first electrode and the second electrode, The organic light-emitting element is characterized in that the organic compound layer has an organic compound as described in any of configurations 1 to 16.

[0242] (Composition 18) The aforementioned organic compound layer has a light-emitting layer, The organic light-emitting element according to configuration 17, characterized in that the light-emitting layer has the organic compound.

[0243] (Composition 19) The light-emitting layer further comprises the first compound, The organic light-emitting element according to configuration 18, characterized in that the lowest singlet excitation energy of the first compound is higher than the lowest singlet excitation energy of the organic compound.

[0244] (Composition 20) The light-emitting layer further comprises a second compound, The organic light-emitting element according to configuration 19, characterized in that the lowest singlet excitation energy of the second compound is higher than the lowest singlet excitation energy of the organic compound and lower than the lowest singlet excitation energy of the first compound.

[0245] (Composition 21) A display device having a plurality of pixels, wherein at least one of the plurality of pixels comprises an organic light-emitting element according to any one of configurations 17 to 20 and a transistor connected to the organic light-emitting element.

[0246] (Composition 22) It has an image sensor that receives light and a display unit that displays the image captured by the image sensor, The photoelectric conversion device is characterized in that the display unit has an organic light-emitting element as described in any of configurations 17 to 20.

[0247] (Composition 23) An image display device characterized by comprising a display unit having an organic light-emitting element as described in any of configurations 17 to 20, and a housing on which the display unit is provided.

[0248] (Composition 24) An electronic device comprising: a display unit having an organic light-emitting element as described in any of configurations 17 to 20; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

[0249] (Composition 25) A wearable device comprising: a display unit having an organic light-emitting element as described in any of configurations 17 to 20; an optical system for focusing light from the display unit; and a control device for controlling the display of the display unit.

[0250] (Composition 26) A lighting device characterized by comprising a light source having an organic light-emitting element as described in any of configurations 17 to 20, and a housing on which the light source is provided.

[0251] (Composition 27) A mobile body characterized by comprising a lamp having an organic light-emitting element as described in any of configurations 17 to 20, and a body on which the lamp is provided. [Explanation of symbols]

[0252] Single-layer insulating layer 2 reflective electrode 3. Insulating layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color Filters 10 subpixels 11 circuit boards 12 Insulating layer 13 gates 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrodes 18 Thin-film transistors 19 Insulating film 20 contact holes 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting diodes 27 Photoreceptor 28 Exposure light source 29 light 30 Charged parts 31. Developing Department 32 Transfer section 33 Conveying section 34 Recording media 35 Fixing section 36 Light-emitting part 37. First direction parallel to the long axis of the photoreceptor. 40 Image forming apparatus 100 display device 1000 display devices 1001 Top cover 1002 Flexible Printed Circuit 1003 Touch Panel 1004 Flexible Printed Circuit 1005 Display Panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation unit 1104 cabinet 1200 Electronic equipment 1201 Display section 1202 Operation unit 1203 enclosure 1300 display device 1301 Picture frame 1302 Display section 1303 Base 1310 Display device 1311 First display section 1312 Second display section 1313 cabinet 1314 Inflection point 1400 Lighting devices 1401 cabinet 1402 Light source 1403 Circuit board 1404 Optical Film 1405 Light Diffusion Section 1500 cars 1501 Taillight 1502 Window 1503 Body 1600 Smart Glasses 1601 Lens 1602 Imaging device 1603 Control device 1610 Smart Glasses 1611 Lens 1612 Control device

Claims

1. An organic compound characterized by being represented by the general formula G1. 【Chemistry 1】 In general formula G1, ring C is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaromatic ring having 5 to 50 carbon atoms. A １１ Even A １５ A ２１ Even A ２５ CR Ａ R is independently selected from the group consisting of nitrogen atoms. Ａ Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. Ａ When there are multiple R Ａ They may be the same or different. X １ and X ２ are each independently selected from the group consisting of an oxygen atom, a sulfur atom, a tellurium atom, a selenium atom, and NR Ｂ where R Ｂ is 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 alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted thioaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted thioheteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a cyano group, and a nitro group. When there are a plurality of R Ｂ the plurality of R Ｂ may be the same or different. Adjacent R Ａ Allies, R Ｂ and substituents on ring C, or adjacent R Ａ and R Ｂ They may combine to form a ring.

2. The organic compound according to claim 1, characterized by being represented by general formula G2 or G3. 【Chemistry 2】 In general formulas G2 and G3, A ３１ A ３２ A ４１ , and A ４２ CR Ｃ R is independently selected from the group consisting of nitrogen atoms. Ｃ Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. Ｃ When there are multiple R Ｃ They may be the same or different. Adjacent R Ｃ R that are the same or adjacent to each other Ｂ and R Ｃ They may combine to form a ring.

3. The organic compound according to claim 2, characterized by being represented by any one of the general formulas G4-1 to G4-10. 【Transformation 3】

4. The organic compound according to claim 3, characterized by being represented by any one of the general formulas G4-1 to G4-5.

5. The organic compound according to claim 3, characterized by being represented by the general formula G4-1.

6. The organic compound according to claim 1, characterized by being represented by any one of the general formulas G5-1 to G5-15. 【Chemistry 4】 In general formulas G5-1 to G5-15, R １１ ~R １５ , R ２１ ~R ２５ , R ３１ , R ３２ , R １１１ ~R １１６ , R ２１１ ~R ２１６ Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. X ３ and X ４ These are oxygen atoms, sulfur atoms, tellurium atoms, selenium atoms, C=O, and NR Ｄ Each is independently selected from the group consisting of R. Ｄ Each of these is independently selected from the group consisting of hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted thioalkoxy groups, substituted or unsubstituted aryl groups, substituted or unsubstituted thioaryl groups, substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted thioheteroaryl groups, substituted or unsubstituted heteroaryloxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, cyano groups, and nitro groups. Ｄ When there are multiple R Ｄ They may be the same or different. R １１ ~R １５ , R ２１ ~R ２５ , R ３１ , R ３２ , R １１１ ~R １１６ , R ２１１ ~R ２１６ , R Ｂ Adjacent elements may be joined together to form a ring.

7. The organic compound according to claim 6, characterized by being represented by any one of the general formulas G5-1 to G5-12.

8. The organic compound according to claim 6, characterized by being represented by any one of the general formulas G5-1 to G5-8.

9. The organic compound according to claim 1, characterized in that ring C is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms.

10. X １ and X ２ It consists of oxygen atoms, sulfur atoms, and NR Ｂ Each of the groups consisting of R is independently selected, Ｂ The organic compound according to claim 1, characterized in that is an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a phenyl group substituted with a deuterium atom.

11. X １ and X ２ The organic compound according to claim 1, characterized in that each of the atoms is independently selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom having a phenyl group.

12. X ３ and X ４ The organic compound according to claim 6, characterized in that each of the atoms is independently selected from the group consisting of an oxygen atom, a sulfur atom, and C=O.

13. A １１ Even A １５ One of them is a nitrogen atom, and the others are CR Ａ And A ２１ Even A ２５ One of them is a nitrogen atom, and the others are CR Ａ The organic compound according to claim 1, characterized in that it is the same as the one described in claim 1.

14. A １１ Even A １５ and A ２１ Even A ２５ CR Ａ The organic compound according to claim 1, characterized in that it is the same as the one described in claim 1.

15. R Ａ The organic compound according to claim 1, characterized in that it is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms, a thioaryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, a heteroaryl group having 3 to 13 carbon atoms, a triphenylsilyl group, an amino group having an alkyl group having 1 to 4 carbon atoms, or an amino group having an aryl group having 6 to 12 carbon atoms.

16. R Ａ The organic compound according to claim 1, characterized in that it is an amino group having a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a phenoxy group, a heteroaryl group having 5 to 12 carbon atoms, or a substituted or unsubstituted phenyl group.

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

18. The aforementioned organic compound layer has a light-emitting layer, The organic light-emitting element according to claim 17, characterized in that the light-emitting layer has the organic compound.

19. The light-emitting layer further comprises the first compound, The organic light-emitting element according to claim 18, characterized in that the lowest singlet excitation energy of the first compound is higher than the lowest singlet excitation energy of the organic compound.

20. The light-emitting layer further comprises a second compound, The organic light-emitting element according to claim 19, characterized in that the lowest singlet excitation energy of the second compound is higher than the lowest singlet excitation energy of the organic compound and lower than the lowest singlet excitation energy of the first compound.

21. A display device having a plurality of pixels, wherein at least one of the plurality of pixels comprises an organic light-emitting element according to any one of claims 17 to 20 and a transistor connected to the organic light-emitting element.

22. It has an image sensor that receives light and a display unit that displays the image captured by the image sensor, The photoelectric conversion device is characterized in that the display unit has an organic light-emitting element as described in any one of claims 17 to 20.

23. An image display device comprising a display unit having an organic light-emitting element as described in any one of claims 17 to 20, and a housing on which the display unit is provided.

24. An electronic device comprising: a display unit having an organic light-emitting element as described in any one of claims 17 to 20; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

25. A wearable device comprising: a display unit having an organic light-emitting element as described in any one of claims 17 to 20; an optical system for focusing light from the display unit; and a control device for controlling the display of the display unit.

26. A lighting device comprising a light source having an organic light-emitting element according to any one of claims 17 to 20, and a housing on which the light source is provided.

27. A mobile body characterized by comprising a lamp having an organic light-emitting element as described in any one of claims 17 to 20, and a body on which the lamp is provided.

Images